U.S. patent application number 16/617297 was filed with the patent office on 2020-08-20 for material for forming underlayer film, resist underlayer film, method of producing resist underlayer film, and laminate.
This patent application is currently assigned to MITSUI CHEMICALS, INC.. The applicant listed for this patent is MITSUI CHEMICALS, INC.. Invention is credited to Koji INOUE, Keisuke KAWASHIMA, Takashi ODA.
Application Number | 20200264511 16/617297 |
Document ID | 20200264511 / US20200264511 |
Family ID | 1000004829640 |
Filed Date | 2020-08-20 |
Patent Application | download [pdf] |
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United States Patent
Application |
20200264511 |
Kind Code |
A1 |
INOUE; Koji ; et
al. |
August 20, 2020 |
MATERIAL FOR FORMING UNDERLAYER FILM, RESIST UNDERLAYER FILM,
METHOD OF PRODUCING RESIST UNDERLAYER FILM, AND LAMINATE
Abstract
A material for forming an underlayer film according to the
present invention is a material for forming an underlayer film
which is used to form a resist underlayer film used in a
multi-layer resist process, the material including a cyclic olefin
polymer which has a repeating structural unit [A] represented by
Formula (1) and a repeating structural unit [B] represented by
Formula (2), in which a molar ratio [A]/[B] of the structural unit
[A] to the structural unit [B] in the cyclic olefin polymer is
greater than or equal to 5/95 and less than or equal to 95/5.
##STR00001##
Inventors: |
INOUE; Koji; (Ichihara-shi,
Chiba, JP) ; ODA; Takashi; (Ichihara-shi, Chiba,
JP) ; KAWASHIMA; Keisuke; (Ichihara-shi, Chiba,
JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
MITSUI CHEMICALS, INC. |
Minato-ku, Tokyo |
|
JP |
|
|
Assignee: |
MITSUI CHEMICALS, INC.
Minato-ku, Tokyo
JP
|
Family ID: |
1000004829640 |
Appl. No.: |
16/617297 |
Filed: |
May 30, 2018 |
PCT Filed: |
May 30, 2018 |
PCT NO: |
PCT/JP2018/020744 |
371 Date: |
November 26, 2019 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C08G 2261/418 20130101;
G03F 7/094 20130101; C08G 2261/3325 20130101; C08G 61/08 20130101;
C09D 165/00 20130101; G03F 7/168 20130101; C08G 2261/228 20130101;
G03F 7/11 20130101 |
International
Class: |
G03F 7/11 20060101
G03F007/11; C08G 61/08 20060101 C08G061/08; C09D 165/00 20060101
C09D165/00; G03F 7/09 20060101 G03F007/09; G03F 7/16 20060101
G03F007/16 |
Foreign Application Data
Date |
Code |
Application Number |
May 31, 2017 |
JP |
2017-108506 |
Oct 6, 2017 |
JP |
2017-196260 |
Claims
1. A material for forming an underlayer film which is used to form
a resist underlayer film used in a multi-layer resist process, the
material comprising: a cyclic olefin polymer which has a repeating
structural unit [A] represented by Formula (1) and a repeating
structural unit [B] represented by Formula (2), wherein a molar
ratio [A]/[B] of the structural unit [A] to the structural unit [B]
in the cyclic olefin polymer is greater than or equal to 5/95 and
less than or equal to 95/5. ##STR00014## (in Formula (1), at least
one of R.sup.1 to R.sup.4 is selected from hydrogen, an alkyl group
having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon
atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy
group having 6 to 20 carbon atoms, an alkoxyalkyl group having 2 to
10 carbon atoms, an aryloxyalkyl group having 7 to 20 carbon atoms,
an alkoxycarbonyl group having 2 to 20 carbon atoms, a
dialkylaminocarbonyl group having 3 to 10 carbon atoms, an
aryloxycarbonyl group having 7 to 20 carbon atoms, an
alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.1 to R.sup.4 may be bonded to one another to form a ring
structure, and n represents an integer of 0 to 2), and ##STR00015##
(in Formula (2), at least one of R.sup.5 to R.sup.8 is selected
from hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl
group having 6 to 20 carbon atoms, an alkoxy group having 1 to 10
carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an
alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 10
carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms,
an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.5 to R.sup.8 may be bonded to one another to form a ring
structure, n represents an integer of 0 to 2, and X.sub.1
represents --O-- or --S--)
2. The material for forming an underlayer film according to claim
1, wherein a temperature showing an intersection between a storage
modulus (G') curve and a loss modulus (G'') curve in a solid
viscoelasticity of the cyclic olefin polymer which are measured
under conditions of a measurement temperature range of 30.degree.
C. to 300.degree. C., a heating rate of 3.degree. C./min, and a
frequency of 1 Hz in a nitrogen atmosphere in a shear mode using a
rheometer is higher than or equal to 40.degree. C. and lower than
or equal to 200.degree. C.
3. The material for forming an underlayer film according to claim
1, wherein a temperature showing an intersection between a storage
modulus (G') curve and a loss modulus (G'') curve in a solid
viscoelasticity of the material for forming an underlayer film
which is measured under conditions of a measurement temperature
range of 30.degree. C. to 300.degree. C., a heating rate of
3.degree. C./min, and a frequency of 1 Hz in a nitrogen atmosphere
in a shear mode using a rheometer is higher than or equal to
40.degree. C. and lower than or equal to 200.degree. C.
4. The material for forming an underlayer film according to claim
2, wherein the temperature showing the intersection between the
storage modulus (G') curve and the loss modulus (G'') curve in the
solid viscoelasticity is higher than or equal to 80.degree. C. and
lower than or equal to 200.degree. C.
5. The material for forming an underlayer film according to claim
1, wherein an amount of a volatile component in the cyclic olefin
polymer which is measured using the following method 1 is greater
than or equal to 0.0% by mass to 1.0% by mass in a case where a
total amount of the cyclic olefin polymer is set to 100% by mass.
(method 1: the cyclic olefin polymer is dissolved in
tetrahydrofuran to prepare a solution having a solid content
concentration of 20% by mass, the obtained solution is weighed
using an aluminum plate, heated at 200.degree. C. for 3 minutes in
a nitrogen flow such that the tetrahydrofuran is removed, and
cooled to room temperature such that the cyclic olefin polymer is
solidified, the cyclic olefin polymer is heated in a temperature
range of 30.degree. C. to 300.degree. C. at a heating rate of
10.degree. C./min in a nitrogen atmosphere, and the amount of the
volatile component in the cyclic olefin polymer is calculated based
on a weight reduction amount in a temperature range of 100.degree.
C. to 250.degree. C.)
6. The material for forming an underlayer film according to claim
1, wherein a weight-average molecular weight (Mw) of the cyclic
olefin polymer in terms of polystyrene which is measured using gel
permeation chromatography is greater than or equal to 1000 and less
than or equal to 20000.
7. The material for forming an underlayer film according to claim
1, wherein a refractive index (n value) of the cyclic olefin
polymer at a wavelength of 193 nm which is measured using the
following method 2 is greater than or equal to 1.5 and less than or
equal to 2.0. (method 2: a coating film which is formed of the
cyclic olefin polymer and has a thickness of 250 nm is formed on a
silicon wafer, and the refractive index (n value) of the obtained
coating film at a wavelength of 193 nm is set as the refractive
index (n value) of the cyclic olefin polymer)
8. The material for forming an underlayer film according to claim
1, wherein a refractive index (n value) of the material for forming
an underlayer film at a wavelength of 193 nm which is measured
using the following method 2 is greater than or equal to 1.5 and
less than or equal to 2.0. (method 2: a coating film which is
formed of the material for forming an underlayer film and has a
thickness of 250 nm is formed on a silicon wafer, and the
refractive index (n value) of the obtained coating film at a
wavelength of 193 nm is set as the refractive index (n value) of
the material for forming an underlayer film)
9. The material for forming an underlayer film according to claim
1, wherein an extinction coefficient (k value) of the cyclic olefin
polymer which is measured using the following method 3 is greater
than or equal to 0.0001 and less than or equal to 0.5. (method 3: a
coating film which is formed of the cyclic olefin polymer and has a
thickness of 250 nm is formed on a silicon wafer, and the
extinction coefficient (k value) of the obtained coating film is
set as the extinction coefficient (k value) of the cyclic olefin
polymer)
10. The material for forming an underlayer film according to claim
1, wherein an extinction coefficient (k value) of the material for
forming an underlayer film which is measured using the following
method 3 is greater than or equal to 0.0001 and less than or equal
to 0.5. (method 3: a coating film which is formed of the material
for forming an underlayer film and has a thickness of 250 nm is
formed on a silicon wafer, and the extinction coefficient (k value)
of the obtained coating film is set as the extinction coefficient
(k value) of the material for forming an underlayer film)
11. The material for forming an underlayer film according to claim
1, which is formed on an uneven structure of a substrate having the
uneven structure and is used for an underlayer film for embedding a
recess in the uneven structure.
12. The material for forming an underlayer film according to claim
1, wherein a content of a crosslinking agent in the material for
forming an underlayer film is less than 5 parts by mass in a case
where a total content of polymer components contained in the
material for forming an underlayer film is set to 100 parts by
mass.
13. The material for forming an underlayer film according to claim
1, wherein a content of the cyclic olefin polymer in the material
for forming an underlayer film is greater than or equal to 50% by
mass and less than or equal to 100% by mass in a case where a total
content of the material for forming an underlayer film is set to
100% by mass.
14. A material for forming an underlayer film which is used to form
a resist underlayer film used in a multi-layer resist process,
wherein the material for forming an underlayer film is a material
of a film containing a cyclic olefin polymer, the cyclic olefin
polymer is soluble in an organic solvent at any concentration of at
least greater than or equal to 0.01% by mass and less than or equal
to 50% by mass, and a residual film rate of the cyclic olefin
polymer in the film which is measured using the following method 4
is greater than or equal to 50% and less than or equal to 100%.
(method 4: a coating film which is formed of the cyclic olefin
polymer and has a thickness (.alpha.) of greater than or equal to
200 nm and less than or equal to 500 nm is formed on a silicon
wafer, the obtained coating film is treated at 200.degree. C. for
10 minutes, immersed in propylene glycol-1-monomethyl
ether-2-acetate at 23.degree. C. for 10 minutes, and dried under
conditions of 150.degree. C. for 3 minutes, and a remaining solvent
in the coating film is removed, and a thickness (.beta.) of the
coating film obtained by removing the remaining solvent is
measured, and the residual film rate (=.beta./.alpha..times.100)
(%) is calculated)
15. A material for forming an underlayer film which is used to form
a resist underlayer film used in a multi-layer resist process, the
material comprising: a cyclic olefin polymer, wherein a residual
film rate of the material for forming an underlayer film which is
measured using the following method 4 is greater than or equal to
50% and less than or equal to 100%. (method 4: a coating film which
is formed of the material for forming an underlayer film and has a
thickness (.alpha.) of greater than or equal to 200 nm and less
than or equal to 500 nm is formed on a silicon wafer, the obtained
coating film is treated at 200.degree. C. for 10 minutes, immersed
in propylene glycol-1-monomethyl ether-2-acetate at 23.degree. C.
for 10 minutes, and dried under conditions of 150.degree. C. for 3
minutes, and a remaining solvent in the coating film is removed,
and a thickness (.beta.) of the coating film obtained by removing
the remaining solvent is measured, and the residual film rate
(=.beta./.alpha..times.100) (%) is calculated)
16. The material for forming an underlayer film according to claim
14, wherein the cyclic olefin polymer has a repeating structural
unit [A] represented by Formula (1) and a repeating structural unit
[B] represented by Formula (2), a molar ratio [A]/[B] of the
structural unit [A] to the structural unit [B] in the cyclic olefin
polymer is greater than or equal to 5/95 and less than or equal to
95/5. ##STR00016## (in Formula (1), at least one of R.sup.1 to
R.sup.4 is selected from hydrogen, an alkyl group having 1 to 10
carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy
group having 1 to 10 carbon atoms, an aryloxy group having 6 to 20
carbon atoms, an alkoxyalkyl group having 2 to 10 carbon atoms, an
aryloxyalkyl group having 7 to 20 carbon atoms, an alkoxycarbonyl
group having 2 to 20 carbon atoms, a dialkylaminocarbonyl group
having 3 to 10 carbon atoms, an aryloxycarbonyl group having 7 to
20 carbon atoms, an alkylarylaminocarbonyl group having 8 to 20
carbon atoms, an alkoxycarbonylalkyl group having 3 to 30 carbon
atoms, an alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.1 to R.sup.4 may be bonded to one another to form a ring
structure, and n represents an integer of 0 to 2), and ##STR00017##
(in Formula (2), at least one of R.sup.5 to R.sup.8 is selected
from hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl
group having 6 to 20 carbon atoms, an alkoxy group having 1 to 10
carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an
alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 10
carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms,
an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.5 to R.sup.8 may be bonded to one another to form a ring
structure, n represents an integer of 0 to 2, and X.sub.1
represents --O-- or --S--)
17. The material for forming an underlayer film according to claim
14, wherein a weight-average molecular weight (Mw) of the cyclic
olefin polymer in terms of polystyrene which is measured using gel
permeation chromatography is greater than or equal to 1000 and less
than or equal to 20000.
18. The material for forming an underlayer film according to claim
14, wherein a refractive index (n value) of the cyclic olefin
polymer at a wavelength of 193 nm which is measured using the
following method 2 is greater than or equal to 1.5 and less than or
equal to 2.0. (method 2: a coating film which is formed of the
cyclic olefin polymer and has a thickness of 250 nm is formed on a
silicon wafer, and the refractive index (n value) of the obtained
coating film at a wavelength of 193 nm is set as the refractive
index (n value) of the cyclic olefin polymer)
19. The material for forming an underlayer film according to claim
14, wherein a refractive index (n value) of the material for
forming an underlayer film at a wavelength of 193 nm which is
measured using the following method 2 is greater than or equal to
1.5 and less than or equal to 2.0. (method 2: a coating film which
is formed of the material for forming an underlayer film and has a
thickness of 250 nm is formed on a silicon wafer, and the
refractive index (n value) of the obtained coating film at a
wavelength of 193 nm is set as the refractive index (n value) of
the material for forming an underlayer film)
20. The material for forming an underlayer film according to claim
14, wherein an extinction coefficient (k value) of the cyclic
olefin polymer which is measured using the following method 3 is
greater than or equal to 0.0001 and less than or equal to 0.5.
(method 3: a coating film which is formed of the cyclic olefin
polymer and has a thickness of 250 nm is formed on a silicon wafer,
and the extinction coefficient (k value) of the obtained coating
film is set as the extinction coefficient (k value) of the cyclic
olefin polymer)
21. The material for forming an underlayer film according to claim
14, wherein an extinction coefficient (k value) of the material for
forming an underlayer film which is measured using the following
method 3 is greater than or equal to 0.0001 and less than or equal
to 0.5. (method 3: a coating film which is formed of the material
for forming an underlayer film and has a thickness of 250 nm is
formed on a silicon wafer, and the extinction coefficient (k value)
of the obtained coating film is set as the extinction coefficient
(k value) of the material for forming an underlayer film)
22. The material for forming an underlayer film according to claim
14, which is formed on an uneven structure of a substrate having
the uneven structure and is used for an underlayer film for
embedding a recess in the uneven structure.
23. The material for forming an underlayer film according claim 14,
wherein a content of a crosslinking agent in the material for
forming an underlayer film is less than 5 parts by mass in a case
where a total content of polymer components contained in the
material for forming an underlayer film is set to 100 parts by
mass.
24. The material for forming an underlayer film according to claim
14, wherein a content of the cyclic olefin polymer in the material
for forming an underlayer film is greater than or equal to 50% by
mass and less than or equal to 100% by mass in a case where a total
content of the material for forming an underlayer film is set to
100% by mass.
25. A resist underlayer film comprising: the material for forming
an underlayer film according to claim 1.
26. A method of producing a resist underlayer film, comprising: a
step of forming a coating film which contains the material for
forming an underlayer film according to claim 1 on a substrate.
27. The method of producing a resist underlayer film according to
claim 26, further comprising: heating the coating film.
28. A laminate comprising: a substrate; and a resist underlayer
film containing the material for forming an underlayer film
according to claim 1, which is formed on one surface of the
substrate.
29. The laminate according to claim 28, wherein a flatness
.DELTA.FT of a surface (.alpha.) of the resist underlayer film on a
side opposite to the substrate which is calculated using the
following equation is greater than or equal to 0% and less than or
equal to 5%. flatness
(.DELTA.FT)=[(H.sub.max-H.sub.min)/H.sub.av].times.100(%) (where
film thicknesses of the resist underlayer film are measured in ten
optional sites of the surface (.alpha.), an average value of these
measured values is set as Hav, a maximum value in the film
thicknesses of the resist underlayer film is set as H.sub.max, and
a minimum value in the film thicknesses of the resist underlayer
film is set as H.sub.min)
30. The laminate according to claim 28, wherein an average value
Hav of the film thickness of the resist underlayer film is greater
than or equal to 5 nm and less than or equal to 1000 nm. (where
film thicknesses of the resist underlayer film are measured in ten
optional sites of the surface (.alpha.) of the resist underlayer
film on the side opposite to the substrate, and the average value
of these measured values is set as Hav)
31. The laminate according to claim 28, wherein the substrate has
an uneven structure on at least one surface thereof, the resist
underlayer film is formed on the uneven structure, the uneven
structure has a height of greater than or equal to 5 nm and less
than or equal to 500 nm, and an interval between projections is
greater than or equal to 1 nm and less than or equal to 10 mm.
Description
TECHNICAL FIELD
[0001] The present invention relates to a material for forming an
underlayer film, a resist underlayer film, a method of producing a
resist underlayer film, and a laminate.
BACKGROUND ART
[0002] In production of a semiconductor device, a multi-layer
resist process has been used to achieve a high degree of
integration. In this process, typically, a resist underlayer film
is firstly formed on a substrate using a material for forming an
underlayer film, a resist layer is formed on an upper surface side
of the resist underlayer film, and the resist layer is baked and
exposed to form a resist pattern. Next, a desired pattern can be
obtained by transferring the resist pattern to the resist
underlayer film through etching and transferring the resist
underlayer film pattern to the substrate.
[0003] A shape of a circuit whose dimension size is large is
further processed using not only a substrate having a flat shape
but also a substrate having an uneven structure preliminarily
formed in a large circuit shape in order to form a more complicated
circuit, and a multi-patterning method for forming a fine circuit
is introduced to the most advanced circuit forming process.
[0004] Such a resist underlayer film used in the multi-layer resist
process is required to have characteristics such as an embedding
property for an uneven portion of a substrate having an uneven
structure, the flatness of a surface on a side where a resist is
applied, a moderate refractive index, and an extinction
coefficient, and characteristics such as excellent etching
resistance.
[0005] In recent years, pattern refinement has been further
promoted in order to increase the degree of integration. In order
to deal with such refinement, various examinations have been
conducted on structures, functional groups, and the like of
compounds used in materials for forming underlayer films (for
example, see Patent Document 1).
[0006] Meanwhile, in the refinement for pattern formation in order
to obtain a high degree of integration, the influence of irregular
reflection or stationary waves from a semiconductor substrate in a
lithography step carried out using an ArF excimer laser which is a
current mainstream has been a major problem. In order to solve this
problem, materials with an anti-reflection function as a function
required for an underlayer film have been widely examined. As a
form in which the anti-reflection function is imparted to an
underlayer film, a form in which an uneven structure of a surface
of a substrate is embedded with a certain kind of a material and a
bottom anti-reflective coating (BARC) is provided on a layer having
a flatness or a form in which an anti-reflection function is
imparted to a material embedding an uneven structure of a surface
of a substrate has been examined.
[0007] Particularly in the former material for forming an
anti-reflective film, various examinations have been conducted on
an organic anti-reflective film formed of a polymer and the like
having a light absorbing site. For example, Patent Document 2
discloses a resist underlayer film (anti-reflective film) which is
not intermixed with a resist film formed on an upper layer and in
which desired optical constants (a refractive index and an
extinction coefficient) are obtained and a selection ratio of a
large dry etching rate with respect to a resist film is obtained in
a case of being exposed to an ArF excimer laser.
RELATED DOCUMENT
Patent Document
[0008] [Patent Document 1] Japanese Unexamined Patent Publication
No. 2004-177668
[0009] [Patent Document 2] International Publication No.
WO2009/008446
SUMMARY OF THE INVENTION
Technical Problem
[0010] Recently, the number of cases of forming finer patterns with
multi-patterning according to a multi-layer resist method, using a
substrate that has a plurality of kinds of trenches and
particularly trenches having aspect ratios different from one
another, that is, a substrate that has a finer uneven structure,
has been increasing. In such cases, a resist layer formed on the
uppermost layer is required to have a high flatness in order to
accurately transfer the pattern on a reticle. In the recent trend
of the pattern refinement, the film thickness of the resist layer
has been decreased in order to avoid pattern collapse in a resist
development step, and thus the resist layer is more strongly
affected by the flatness of the underlayer film. Therefore, a
resist underlayer film formed on a substrate having a surface
structure into which a resin is unlikely to infiltrate as described
above is formed such that these trenches are sufficiently embedded
and is required to have a high flatness. In addition, it is
considered that a material that does not generate volatile
components (outgas) in a baking step after application is
preferable.
[0011] According to the examination conducted by the present
inventors, it was found that a material which satisfies the
requirement for the flatness and does not generate volatile
components is unlikely to be realized in materials for forming a
resist underlayer film of the related art.
[0012] In the lithography that employs EUV (abbreviation for
extreme ultraviolet, a wavelength of 13.5 nm) which is another fine
processing technology, particularly, generation of volatile
components (outgas) of a material that forms a resist underlayer
film for exposure to high energy ray of EUV light may become a
major problem, in addition to the embedding property of the related
art even though there is no reflection from a substrate.
[0013] Further, in a case where a circuit view is drawn with a line
width less than or equal to the wavelength of exposure light, a
method of forming a plurality of uneven layers and combining the
formed layers has been known. In order to realize such an aspect, a
method of forming an intermediate layer on an underlayer film for
the purpose of smoothing the uneven layer and further forming a new
resist layer thereon can be exemplified.
[0014] According to the examination conducted by the present
inventors, for example, in a case where this intermediate layer is
formed according to a spin coating method or the like, a wrong
choice of a solvent may lead to intermixing of the underlayer film
with the intermediate film. As the result, it was found that the
interface strength between the underlayer film and the intermediate
layer may be degraded or the smoothness of the underlayer film may
be lost.
[0015] The first present invention has been made in consideration
of the above-described circumstances, and an object thereof is to
provide a material for forming an underlayer film which enables
realization of a resist underlayer film having sufficient optical
characteristics, etching resistance, excellent flatness, and a
suppressed generation of volatile components.
[0016] Further, another object of the first present invention is to
provide a material for forming an underlayer film, which enables
formation of a resist underlayer film having an excellent embedding
property for an uneven structure, sufficient optical
characteristics, etching resistance, excellent flatness, and a
suppressed generation of volatile components on a substrate having
a complicated shape.
[0017] Further, the second present invention has been made in
consideration of the above-described circumstances, and an object
thereof is to provide a material for forming an underlayer film
which enables realization of a laminate having excellent
adhesiveness and excellent flatness without causing intermixing of
an intermediate layer with a resist underlayer film.
Solution to Problem
[0018] According to the present invention, provided are a material
for forming an underlayer film, a resist underlayer film, a method
of producing a resist underlayer film, and a laminate described
below.
[1]
[0019] A material for forming an underlayer film which is used to
form a resist underlayer film used in a multi-layer resist process,
the material including: a cyclic olefin polymer which has a
repeating structural unit [A] represented by Formula (1) and a
repeating structural unit [B] represented by Formula (2), in which
a molar ratio [A]/[B] of the structural unit [A] to the structural
unit [B] in the cyclic olefin polymer is greater than or equal to
5/95 and less than or equal to 95/5.
##STR00002##
[0020] (in Formula (1), at least one of R.sup.1 to R.sup.4 is
selected from hydrogen, an alkyl group having 1 to 10 carbon atoms,
an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1
to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms,
an alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 10
carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms,
an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.1 to R.sup.4 may be bonded to one another to form a ring
structure, and n represents an integer of 0 to 2), and
##STR00003##
[0021] (in Formula (2), at least one of R.sup.5 to R.sup.8 is
selected from hydrogen, an alkyl group having 1 to 10 carbon atoms,
an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1
to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms,
an alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 10
carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms,
an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.5 to R.sup.8 may be bonded to one another to form a ring
structure, n represents an integer of 0 to 2, and X.sub.1
represents --O-- or --S--)
[2]
[0022] The material for forming an underlayer film according to
[1], in which a temperature showing an intersection between a
storage modulus (G') curve and a loss modulus (G'') curve in a
solid viscoelasticity of the cyclic olefin polymer which is
measured under conditions of a measurement temperature range of
30.degree. C. to 300.degree. C., a heating rate of 3.degree.
C./min, and a frequency of 1 Hz in a nitrogen atmosphere in a shear
mode using a rheometer is higher than or equal to 40.degree. C. and
lower than or equal to 200.degree. C.
[3]
[0023] The material for forming an underlayer film according to
[1], in which a temperature showing an intersection between a
storage modulus (G') curve and a loss modulus (G'') curve in a
solid viscoelasticity of the material for forming an underlayer
film which is measured under conditions of a measurement
temperature range of 30.degree. C. to 300.degree. C., a heating
rate of 3.degree. C./min, and a frequency of 1 Hz in a nitrogen
atmosphere in a shear mode using a rheometer is higher than or
equal to 40.degree. C. and lower than or equal to 200.degree.
C.
[4]
[0024] The material for forming an underlayer film according to [2]
or [3], in which the temperature showing the intersection between
the storage modulus (G') curve and the loss modulus (G'') curve in
the solid viscoelasticity is higher than or equal to 80.degree. C.
and lower than or equal to 200.degree. C.
[5]
[0025] The material for forming an underlayer film according to any
one of [1] to [4], in which an amount of a volatile component in
the cyclic olefin polymer which is measured using the following
method 1 is greater than or equal to 0.0% by mass to 1.0% by mass
in a case where a total amount of the cyclic olefin polymer is set
to 100% by mass.
(method 1: the cyclic olefin polymer is dissolved in
tetrahydrofuran to prepare a solution having a solid content
concentration of 20% by mass, the obtained solution is weighed
using an aluminum plate, heated at 200.degree. C. for 3 minutes in
a nitrogen flow such that the tetrahydrofuran is removed, and
cooled to room temperature such that the cyclic olefin polymer is
solidified, the cyclic olefin polymer is heated in a temperature
range of 30.degree. C. to 300.degree. C. at a heating rate of
10.degree. C./min in a nitrogen atmosphere, and the amount of the
volatile component in the cyclic olefin polymer is calculated based
on a weight reduction amount in a temperature range of 100.degree.
C. to 250.degree. C.) [6]
[0026] The material for forming an underlayer film according to any
one of [1] to [5], in which a weight-average molecular weight (Mw)
of the cyclic olefin polymer in terms of polystyrene which is
measured using gel permeation chromatography is greater than or
equal to 1000 and less than or equal to 20000.
[7]
[0027] The material for forming an underlayer film according to any
one of [1] to [6], in which a refractive index (n value) of the
cyclic olefin polymer at a wavelength of 193 nm which is measured
using the following method 2 is greater than or equal to 1.5 and
less than or equal to 2.0.
(method 2: a coating film which is formed of the cyclic olefin
polymer and has a thickness of 250 nm is formed on a silicon wafer,
and the refractive index (n value) of the obtained coating film at
a wavelength of 193 nm is set as the refractive index (n value) of
the cyclic olefin polymer) [8]
[0028] The material for forming an underlayer film according to any
one of [1] to [6], in which a refractive index (n value) of the
material for forming an underlayer film at a wavelength of 193 nm
which is measured using the following method 2 is greater than or
equal to 1.5 and less than or equal to 2.0.
(method 2: a coating film which is formed of the material for
forming an underlayer film and has a thickness of 250 nm is formed
on a silicon wafer, and the refractive index (n value) of the
obtained coating film at a wavelength of 193 nm is set as the
refractive index (n value) of the material for forming an
underlayer film) [9]
[0029] The material for forming an underlayer film according to any
one of [1] to [8], in which an extinction coefficient (k value) of
the cyclic olefin polymer which is measured using the following
method 3 is greater than or equal to 0.0001 and less than or equal
to 0.5.
(method 3: a coating film which is formed of the cyclic olefin
polymer and has a thickness of 250 nm is formed on a silicon wafer,
and the extinction coefficient (k value) of the obtained coating
film is set as the extinction coefficient (k value) of the cyclic
olefin polymer) [10]
[0030] The material for forming an underlayer film according to any
one of [1] to [8], in which an extinction coefficient (k value) of
the material for forming an underlayer film which is measured using
the following method 3 is greater than or equal to 0.0001 and less
than or equal to 0.5.
(method 3: a coating film which is formed of the material for
forming an underlayer film and has a thickness of 250 nm is formed
on a silicon wafer, and the extinction coefficient (k value) of the
obtained coating film is set as the extinction coefficient (k
value) of the material for forming an underlayer film) [11]
[0031] The material for forming an underlayer film according to any
one of [1] to [10], which is formed on an uneven structure of a
substrate having the uneven structure and is used for an underlayer
film for embedding a recess in the uneven structure.
[12]
[0032] The material for forming an underlayer film according to any
one of [1] to [11], in which a content of a crosslinking agent in
the material for forming an underlayer film is less than 5 parts by
mass in a case where a total content of polymer components
contained in the material for forming an underlayer film is set to
100 parts by mass.
[13]
[0033] The material for forming an underlayer film according to any
one of [1] to [12], in which a content of the cyclic olefin polymer
in the material for forming an underlayer film is greater than or
equal to 50% by mass and less than or equal to 100% by mass in a
case where a total content of the material for forming an
underlayer film is set to 100% by mass.
[14]
[0034] A material for forming an underlayer film which is used to
form a resist underlayer film used in a multi-layer resist process,
in which the material for forming an underlayer film is a material
of a film containing a cyclic olefin polymer, the cyclic olefin
polymer is soluble in an organic solvent at any concentration of at
least greater than or equal to 0.01% by mass and less than or equal
to 50% by mass, and a residual film rate of the cyclic olefin
polymer in the film which is measured using the following method 4
is greater than or equal to 50% and less than or equal to 100%.
(method 4: a coating film which is formed of the cyclic olefin
polymer and has a thickness (a) of greater than or equal to 200 nm
and less than or equal to 500 nm is formed on a silicon wafer, the
obtained coating film is treated at 200.degree. C. for 10 minutes,
immersed in propylene glycol-1-monomethyl ether-2-acetate at
23.degree. C. for 10 minutes, and dried under conditions of
150.degree. C. for 3 minutes, and a remaining solvent in the
coating film is removed, and a thickness (.beta.) of the coating
film obtained by removing the remaining solvent is measured, and
the residual film rate (=.beta./.alpha..times.100) (%) is
calculated) [15]
[0035] A material for forming an underlayer film which is used to
form a resist underlayer film used in a multi-layer resist process,
the material including: a cyclic olefin polymer, in which a
residual film rate of the material for forming an underlayer film
which is measured using the following method 4 is greater than or
equal to 50% and less than or equal to 100%.
(method 4: a coating film which is formed of the material for
forming an underlayer film and has a thickness (a) of greater than
or equal to 200 nm and less than or equal to 500 nm is formed on a
silicon wafer, the obtained coating film is treated at 200.degree.
C. for 10 minutes, immersed in propylene glycol-1-monomethyl
ether-2-acetate at 23.degree. C. for 10 minutes, and dried under
conditions of 150.degree. C. for 3 minutes, and a remaining solvent
in the coating film is removed, and a thickness (.beta.) of the
coating film obtained by removing the remaining solvent is
measured, and the residual film rate (=.beta./.alpha..times.100)
(%) is calculated) [16]
[0036] The material for forming an underlayer film according to
[14] or [15], in which the cyclic olefin polymer has a repeating
structural unit [A] represented by Formula (1) and a repeating
structural unit [B] represented by Formula (2), a molar ratio
[A]/[B] of the structural unit [A] to the structural unit [B] in
the cyclic olefin polymer is greater than or equal to 5/95 and less
than or equal to 95/5.
##STR00004##
[0037] (in Formula (1), at least one of R.sup.1 to R.sup.4 is
selected from hydrogen, an alkyl group having 1 to 10 carbon atoms,
an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1
to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms,
an alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 10
carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms,
an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.1 to R.sup.4 may be bonded to one another to form a ring
structure, and n represents an integer of 0 to 2), and
##STR00005##
[0038] (in Formula (2), at least one of R.sup.5 to R.sup.8 is
selected from hydrogen, an alkyl group having 1 to 10 carbon atoms,
an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1
to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms,
an alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 10
carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms,
an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.5 to R.sup.8 may be bonded to one another to form a ring
structure, n represents an integer of 0 to 2, and X.sub.1
represents --O-- or --S--)
[17]
[0039] The material for forming an underlayer film according to any
one of [14] to [16], in which a weight-average molecular weight
(Mw) of the cyclic olefin polymer in terms of polystyrene which is
measured using gel permeation chromatography is greater than or
equal to 1000 and less than or equal to 20000.
[18]
[0040] The material for forming an underlayer film according to any
one of [14] to [17], in which a refractive index (n value) of the
cyclic olefin polymer at a wavelength of 193 nm which is measured
using the following method 2 is greater than or equal to 1.5 and
less than or equal to 2.0.
(method 2: a coating film which is formed of the cyclic olefin
polymer and has a thickness of 250 nm is formed on a silicon wafer,
and the refractive index (n value) of the obtained coating film at
a wavelength of 193 nm is set as the refractive index (n value) of
the cyclic olefin polymer) [19]
[0041] The material for forming an underlayer film according to any
one of [14] to [17],
[0042] in which a refractive index (n value) of the material for
forming an underlayer film at a wavelength of 193 nm which is
measured using the following method 2 is greater than or equal to
1.5 and less than or equal to 2.0.
(method 2: a coating film which is formed of the material for
forming an underlayer film and has a thickness of 250 nm is formed
on a silicon wafer, and the refractive index (n value) of the
obtained coating film at a wavelength of 193 nm is set as the
refractive index (n value) of the material for forming an
underlayer film) [20]
[0043] The material for forming an underlayer film according to any
one of [14] to [19], in which an extinction coefficient (k value)
of the cyclic olefin polymer which is measured using the following
method 3 is greater than or equal to 0.0001 and less than or equal
to 0.5.
(method 3: a coating film which is formed of the cyclic olefin
polymer and has a thickness of 250 nm is formed on a silicon wafer,
and the extinction coefficient (k value) of the obtained coating
film is set as the extinction coefficient (k value) of the cyclic
olefin polymer) [21]
[0044] The material for forming an underlayer film according to any
one of [14] to [19], in which an extinction coefficient (k value)
of the material for forming an underlayer film which is measured
using the following method 3 is greater than or equal to 0.0001 and
less than or equal to 0.5.
(method 3: a coating film which is formed of the material for
forming an underlayer film and has a thickness of 250 nm is formed
on a silicon wafer, and the extinction coefficient (k value) of the
obtained coating film is set as the extinction coefficient (k
value) of the material for forming an underlayer film) [22]
[0045] The material for forming an underlayer film according to any
one of [14] to [21], which is formed on an uneven structure of a
substrate having the uneven structure and is used for an underlayer
film for embedding a recess in the uneven structure.
[23]
[0046] The material for forming an underlayer film according to any
one of [14] to [22], in which a content of a crosslinking agent in
the material for forming an underlayer film is less than 5 parts by
mass in a case where a total content of polymer components
contained in the material for forming an underlayer film is set to
100 parts by mass.
[24]
[0047] The material for forming an underlayer film according to any
one of [14] to [23], in which a content of the cyclic olefin
polymer in the material for forming an underlayer film is greater
than or equal to 50% by mass and less than or equal to 100% by mass
in a case where a total content of the material for forming an
underlayer film is set to 100% by mass.
[25]
[0048] A resist underlayer film including: the material for forming
an underlayer film according to any one of [1] to [24].
[26]
[0049] A method of producing a resist underlayer film, including: a
step of forming a coating film which contains the material for
forming an underlayer film according to any one of [1] to [24] on a
substrate.
[27]
[0050] The method of producing a resist underlayer film according
to [26], further including: heating the coating film.
[28]
[0051] A laminate including: a substrate; and a resist underlayer
film containing the material for forming an underlayer film
according to any one of [1] to [24], which is formed on one surface
of the substrate.
[29]
[0052] The laminate according to [28], in which a flatness
.DELTA.FT of a surface (.alpha.) of the resist underlayer film on a
side opposite to the substrate which is calculated using the
following equation is greater than or equal to 0% and less than or
equal to 5%.
flatness
(.DELTA.FT)=[(H.sub.max-H.sub.min)/H.sub.av].times.100(%)
[0053] (where film thicknesses of the resist underlayer film are
measured in ten optional sites of the surface (.alpha.), an average
value of these measured values is set as Hay, a maximum value in
the film thicknesses of the resist underlayer film is set as
H.sub.max, and a minimum value in the film thicknesses of the
resist underlayer film is set as H.sub.min)
[30]
[0054] The laminate according to [28] or [29], in which an average
value Hav of the film thickness of the resist underlayer film is
greater than or equal to 5 nm and less than or equal to 1000
nm.
[0055] (where film thicknesses of the resist underlayer film are
measured in ten optional sites of the surface (.alpha.) of the
resist underlayer film on the side opposite to the substrate, and
the average value of these measured values is set as Hav)
[31]
[0056] The laminate according to any one of [28] to [30], in which
the substrate has an uneven structure on at least one surface
thereof, the resist underlayer film is formed on the uneven
structure, the uneven structure has a height of greater than or
equal to 5 nm and less than or equal to 500 nm, and an interval
between projections is greater than or equal to 1 nm and less than
or equal to 10 mm.
Advantageous Effects of Invention
[0057] According to the first present invention, it is possible to
provide a material for forming an underlayer film which enables
realization of a resist underlayer film having sufficient optical
characteristics, etching resistance, excellent flatness, and a
suppressed generation of volatile components.
[0058] Further, according to the present invention, since the
material for forming an underlayer film of the first present
invention has an excellent embedding property for an uneven
structure, it is possible to form a resist underlayer film having
an excellent embedding property for an uneven structure, sufficient
optical characteristics, etching resistance, excellent flatness,
and a suppressed generation of volatile components on a substrate
having a complicated shape.
[0059] Further, according to the second present invention, it is
possible to provide a material for forming an underlayer film which
enables realization of a laminate having excellent adhesiveness and
excellent flatness without causing intermixing of an intermediate
layer with a resist underlayer film.
BRIEF DESCRIPTION OF THE DRAWINGS
[0060] The above-described objects, other objects, features, and
advantages will become more apparent based on preferred embodiments
described below and the accompanying drawings.
[0061] FIG. 1 shows a storage modulus (G') curve, a loss modulus
(G'') curve, and an intersection of these curves in measurement of
the solid viscoelasticity of a polymer 1 described in Example
1.
[0062] FIG. 2 is a schematic view for describing the thickness of a
resist underlayer film, the height of an uneven structure, and an
interval between a recess and a projection of the uneven structure
in a laminate according to an embodiment of the present
invention.
[0063] FIG. 3 is a schematic view for describing an uneven
structure in which the intervals between recesses and projections,
the heights of the projections, and the widths of the projections
according to an embodiment of the present invention are not
uniform.
[0064] FIG. 4 is a TEM microphotograph showing a cross section of a
wafer obtained by being overcoated with a polymer 19 described in
Example 28 and TiO.sub.2.
DESCRIPTION OF EMBODIMENTS
[0065] Hereinafter, embodiments of the present invention will be
described.
[0066] A numerical range of "A to B" indicates greater than or
equal to A and less than or equal to B unless otherwise
specified.
[First Invention]
[0067] Hereinafter, an embodiment according to the first invention
will be described.
<Material for Forming Underlayer Film>
[0068] A material for forming an underlayer film according to the
present embodiment is a material for forming an underlayer film
which is used to form a resist underlayer film used in a
multi-layer resist process. The material includes a cyclic olefin
polymer which has a repeating structural unit [A] represented by
Formula (1) and a repeating structural unit [B] represented by
Formula (2), and the molar ratio [A]/[B] of the structural unit [A]
to the structural unit [B] in the cyclic olefin polymer is greater
than or equal to 5/95 and less than or equal to 95/5.
[0069] The material for forming an underlayer film according to the
present embodiment is a material for forming a layer disposed
between a resist layer and a substrate (preferably a substrate
having an uneven structure) in a step of producing a semiconductor
device. The layer disposed between the resist layer and the
substrate is typically referred to as a resist underlayer film,
based on a resist layer formed of a resist material that transfers
a mask pattern in a photolithography process. The surface of the
substrate which comes into contact with the resist underlayer film
may be in a state in which a coating film is formed of a low
dielectric material, such as a silica (SiO.sub.2) film, a SiCN
film, a SiOC film obtained by doping silica (SiO.sub.2) with carbon
(C), a methylsiloxane-based organic film (SOG), or a silica
insulating film in which minute holes having a size of several
nanometers or less are uniformly distributed.
[0070] In a case where the material for forming an underlayer film
according to the present embodiment contains a cyclic olefin
polymer having a repeating structural unit [A] represented by
Formula (1) and a repeating structural unit [B] represented by
Formula (2), a resist underlayer film having sufficient optical
characteristics, etching resistance, excellent flatness, and a
suppressed generation of volatile components can be formed. In
other words, the material for forming an underlayer film according
to the present embodiment can be suitably used for forming a resist
underlayer film.
[0071] In the material for forming an underlayer film according to
the present embodiment, the content of the cyclic olefin polymer
having a repeating structural unit [A] represented by Formula (1)
and a repeating structural unit [B] represented by Formula (2) is
preferably greater than or equal to 50% by mass and less than or
equal to 100% by mass, more preferably greater than or equal to 70%
and less than or equal to 100% by mass, still more preferably
greater than or equal to 80% and less than or equal to 100% by
mass, and particularly preferably greater than or equal to 90% by
mass and less than or equal to 100% by mass with respect to 100% by
mass which is the total content of the material for forming an
underlayer film.
[0072] It is preferable that the same applies to a cyclic olefin
polymer in the second invention described below.
[0073] The molar ratio [A]/[B] of the structural unit [A] to the
structural unit [B] in the cyclic olefin polymer is greater than or
equal to 5/95 and less than or equal to 95/5, preferably greater
than or equal to 7/93 and less than or equal to 93/7, more
preferably greater than or equal to 10/90 and less than or equal to
90/10, and still more preferably greater than or equal to 15/85 and
less than or equal to 85/15.
[0074] According to the present inventors, it is considered that in
a case where the composition of the cyclic olefin polymer is in the
above-described range, the density of elements such as oxygen and
sulfur in the main chain of the polymer is in a suitable range,
appropriate adhesiveness to the interface of the substrate can be
exhibited at the time of embedding the uneven structure of the
substrate, occurrence of voids and the like can be suppressed, and
the embedding property in an excellent state while maintaining high
flatness can be realized. Further, the interaction with the
substrate due to the presence of elements such as oxygen and sulfur
in the main chain of the cyclic olefin polymer is assumed to become
a driving force for the cyclic olefin polymer to enter the fine
uneven structure.
[0075] In other words, the material for forming an underlayer film
according to the present embodiment is formed on the uneven
structure of the substrate having the uneven structure and can be
particularly suitably used to form an underlayer film for embedding
recesses in the uneven structure.
[0076] In a case where the ratio [A]/[B] is out of the
above-described ranges of the upper limit and the lower limit, the
adhesiveness to the interface of the substrate is not exhibited in
a cooling process after application to the uneven substrate and
baking, and the material is contracted and this may cause defects
such as voids.
[0077] In the present embodiment, the repeating structural unit [A]
represented by Formula (1) and the repeating structural unit [B]
represented by Formula (2) are represented by the following
formulae. Here, the dotted lines in the main chain portions in
Formulae (1) and (2) each indicate one covalent bond constituting a
double bond or a state in which a double bond is hydrogenated and
one covalent bond constituting the double bond is lost.
##STR00006##
(In Formula (1), at least one of R.sup.1 to R.sup.4 is selected
from hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl
group having 6 to 20 carbon atoms, an alkoxy group having 1 to 10
carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an
alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms (preferably 2 to 10 carbon atoms), a
dialkylaminocarbonyl group having 3 to 10 carbon atoms, an
aryloxycarbonyl group having 7 to 20 carbon atoms, an
alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms (preferably 3
to 20 carbon atoms), an alkoxycarbonylaryl group having 8 to 30
carbon atoms, an aryloxycarbonylalkyl group having 8 to 20 carbon
atoms, an alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms,
and an alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon
atoms (preferably 4 to 20 carbon atoms), R.sup.1 to R.sup.4 may be
bonded to one another to form a ring structure, and n represents an
integer of 0 to 2.)
##STR00007##
(In Formula (2), at least one of R.sup.5 to R.sup.8 is selected
from hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl
group having 6 to 20 carbon atoms, an alkoxy group having 1 to 10
carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an
alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms (preferably 2 to 10 carbon atoms), a
dialkylaminocarbonyl group having 3 to 10 carbon atoms, an
aryloxycarbonyl group having 7 to 20 carbon atoms, an
alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms (preferably 3
to 20 carbon atoms), an alkoxycarbonylaryl group having 8 to 30
carbon atoms, an aryloxycarbonylalkyl group having 8 to 20 carbon
atoms, an alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms,
and an alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon
atoms (preferably 4 to 20 carbon atoms), R.sup.5 to R.sup.8 may be
bonded to one another to form a ring structure, n represents an
integer of 0 to 2, and X.sub.1 represents --O-- or --S--.)
[0078] Examples of the alkyl group having 1 to 10 carbon atoms as
R.sup.1 to R.sup.4 in Formula (1) include a methyl group, an ethyl
group, an n-propyl group, an i-propyl group, an n-butyl group, a
tert-butyl group, an n-pentyl group, a cyclopentyl group, a
cyclohexyl group, and a cyclooctyl group. Examples of the aryl
group having 6 to 20 carbon atoms include a phenyl group, a
naphthyl group, an anthracenyl group, an o-tolyl group, an m-tolyl
group, a p-tolyl group, a biphenyl group, and a phenol group.
Examples of the alkoxy group having 1 to 10 carbon atoms include a
methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy
group, an n-butoxy group, a tert-butoxy group, an n-pentoxy group,
a cyclopentoxy group, a cyclohexyloxy group, and a cyclooctyloxy
group. Examples of the aryloxy group having 6 to 20 carbon atoms
include a phenyloxy group, a naphthyloxy group, an anthracenyloxy
group, an o-tolyloxy group, an m-tolyloxy group, a p-tolyloxy
group, a 4-oxy-1,1'-biphenyl group, and a 4-hydroxyphenyloxy group.
Examples of the alkoxyalkyl group having 2 to 10 carbon atoms
include a methoxymethyl group, a methoxyethyl group, an
ethoxymethyl group, an ethoxyethyl group, an n-propoxymethyl group,
an isopropoxymethyl group, an n-butoxymethyl group, an
isobutoxymethyl group, a tert-butoxymethyl group, a
cyclopentyloxymethyl group, a cyclohexyloxymethyl group, and a
cyclooctyloxymethyl group. Examples of the aryloxyalkyl group
having 7 to 20 carbon atoms include a phenyloxymethyl group, a
naphthyloxymethyl group, an anthracenyloxymethyl group, an
o-tolyloxymethyl group, an m-tolyloxymethyl group, a
p-tolyloxymethyl group, a 4-oxy-1,1'-biphenylmethyl group, and a
4-hydroxyphenyloxymethyl group. Examples of the alkoxycarbonyl
group having 2 to 20 carbon atoms include a methoxycarbonyl group,
an ethoxycarbonyl group, an n-propoxycarbonyl group, an
n-butoxycarbonyl group, an isobutoxycarbonyl group, a
tert-butoxycarbonyl group, an n-pentyloxycarbonyl group, a
cyclopentyloxycarbonyl group, an n-hexyloxycarbonyl group, a
cyclohexyloxycarbonyl group, a 3-methylbutoxycarbonyl group, a
2-methylpentoxycarbonyl group, a 3-methylpentoxycarbonyl group, a
4-methylpentoxycarbonyl group, a 1-ethylcyclopentyloxycarbonyl
group, a 1-methylcyclohexyloxycarbonyl group, a
norbornyloxycarbonyl group, and an adamantyloxycarbonyl group.
Examples of the dialkylaminocarbonyl group having 3 to 10 carbon
atoms include a dimethylaminocarbonyl group, a diethylaminocarbonyl
group, an ethylmethylaminocarbonyl group, a
methylbutylaminocarbonyl group, a butylethylaminocarbonyl group,
and a cyclohexylmethylaminocarbonyl group. Examples of the
aryloxycarbonyl group having 7 to 20 carbon atoms include a
phenoxycarbonyl group, a benzyloxycarbonyl group, a
4-methylphenoxycarbonyl group, a 3,4-dimethylphenoxycarbonyl group,
a 1-naphthoxycarbonyl group, a 2-naphthoxycarbonyl group, and a
1-anthracenoxycarbonyl group. Examples of the
alkylarylaminocarbonyl group having 8 to 20 carbon atoms include a
methylphenylaminocarbonyl group, an ethylphenylaminocarbonyl group,
a butylphenylaminocarbonyl group, and a
cyclohexylphenylaminocarbonyl group. Examples of the
alkoxycarbonylalkyl group having 3 to 30 carbon atoms include a
methoxycarbonylmethyl group, a methoxycarbonylethyl group, an
ethoxycarbonylmethyl group, an ethoxycarbonylethyl group, an
n-propoxycarbonylmethyl group, an i-propoxycarbonylmethyl group, an
n-butoxycarbonylmethyl group, a tert-butoxycarbonylmethyl group, an
n-pentyloxycarbonylmethyl group, a cyclopentyloxycarbonylmethyl
group, an n-hexyloxycarbonylmethyl group, a
cyclohexyloxycarbonylmethyl group, an n-octyloxycarbonylmethyl
group, a cyclooctyloxycarbonylmethyl group, a
1-ethylcyclopentyloxycarbonylmethyl group, and a
1-methylcyclohexyloxycarbonylmethyl group. Examples of the
alkoxycarbonylaryl group having 8 to 30 carbon atoms include a
methoxycarbonylphenyl group, a methoxycarbonyl-o-tolyl group, a
methoxycarbonyl-m-tolyl group, a methoxycarbonyl-p-tolyl group, a
methoxycarbonylsilyl group, a methoxycarbonyl-.alpha.-naphthyl
group, a methoxycarbonyl-.beta.-naphthyl group, an
ethoxycarbonylphenyl group, a propoxycarbonylphenyl group, a
butoxycarbonylphenyl group, an ethoxycarbonylphenyl group, an
n-propoxycarbonylphenyl group, an i-propoxycarbonylphenyl group, an
n-butoxycarbonylphenyl group, a tert-butoxycarbonylphenyl group, an
n-pentyloxycarbonylphenyl group, a cyclopentyloxycarbonylphenyl
group, an n-hexyloxycarbonylphenyl group, a
cyclohexyloxycarbonylphenyl group, an n-octyloxycarbonylphenyl
group, a cyclooctyloxycarbonylphenyl group, a
1-ethylcyclopentyloxycarbonylphenyl group, a
1-methylcyclohexyloxycarbonylphenyl group, a
methoxycarbonylnaphthyl group, a methoxycarbonylethyl group, an
ethoxycarbonylnaphthyl group, an n-propoxycarbonylnaphthyl group,
an i-propoxycarbonylnaphthyl group, an n-butoxycarbonylnaphthyl
group, a tert-butoxycarbonylnaphthyl group, an
n-pentyloxycarbonylnaphthyl group, a cyclopentyloxycarbonylnaphthyl
group, an n-hexyloxycarbonylnaphthyl group, a
cyclohexyloxycarbonylnaphthyl group, an n-octyloxycarbonylnaphthyl
group, a cyclooctyloxycarbonylnaphthyl group, a
1-ethylcyclopentyloxycarbonylnaphthyl group, and a
1-methylcyclohexyloxycarbonylnaphthyl group. Examples of the
aryloxycarbonylalkyl group having 8 to 20 carbon atoms include a
phenoxycarbonylmethyl group, a benzyloxycarbonylmethyl group, a
4-methylphenoxycarbonylmethyl group, a
3,4-dimethylphenoxycarbonylmethyl group, a
1-naphthoxycarbonylmethyl group, a 2-naphthoxycarbonylmethyl group,
and a 1-anthracenoxycarbonylmethyl group. Examples of the
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms include a
methoxymethyloxycarbonyl group, an ethoxymethyloxycarbonyl group,
an n-propoxymethyloxycarbonyl group, an isopropoxymethyloxycarbonyl
group, an n-butoxymethyloxycarbonyl group, a
tert-butoxymethyloxycarbonyl group, a
cyclopentyloxymethyloxycarbonyl group, a
cyclohexyloxymethyloxycarbonyl group, a
cyclooctyloxymethyloxycarbonyl group, a
norbornyloxymethyloxycarbonyl group, a
1-methylcyclopentyloxymethyloxycarbonyl group, a
1-ethylcyclopentyloxymethyloxycarbonyl group, a
1-methylcyclohexyloxymethyloxycarbonyl group, a
1-methylnorbornyloxymethyloxycarbonyl group, a
1-ethylnorbornyloxymethyloxycarbonyl group, a
1-ethoxypropyloxymethyloxycarbonyl group, a
1-ethoxy-1-methylethyloxymethyloxycarbonyl group, a
tetrahydrofuran-2-yloxymethyloxycarbonyl group, a
tetrahydropyran-2-yloxymethyloxycarbonyl group, a
1-adamantyloxymethyloxycarbonyl group, and a
2-adamantyloxymethyloxycarbonyl group. Examples of the
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms
include a methoxycarbonylmethyloxycarbonyl group, an
ethoxycarbonylmethyloxycarbonyl group, an
n-propoxycarbonylmethyloxycarbonyl group, an
isopropoxycarbonylmethyloxycarbonyl group, an
n-butoxycarbonylmethyloxycarbonyl group, a
tert-butoxycarbonylmethyloxycarbonyl group, a
cyclopentyloxycarbonylmethyloxycarbonyl group, a
cyclohexyloxycarbonylmethyloxycarbonyl group, a
cyclooctyloxycarbonylmethyloxycarbonyl group, a
norbornyloxycarbonylmethyloxycarbonyl group, a
1-methylcyclopentyloxycarbonylmethyloxycarbonyl group, a
1-ethylcyclopentyloxycarbonylmethyloxycarbonyl group, a
1-methylcyclohexyloxycarbonylmethyloxycarbonyl group, a
1-methylnorbornyloxycarbonylmethyloxycarbonyl group, a
1-ethylnorbornyloxycarbonylmethyloxycarbonyl group, a
1-ethoxypropyloxycarbonylmethyloxycarbonyl group, a
1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl group, a
tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl group, a
tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl group, a
1-adamantyloxycarbonylmethyloxycarbonyl group, and a
2-adamantyloxycarbonylmethyloxycarbonyl group.
[0079] Further, R.sup.1 to R.sup.4 may form a ring structure.
Specifically, R.sup.1 to R.sup.4 are each independently bonded to
one another or at least two of these are bonded to each other to
form a ring structure optionally through a --C-- bond, a --O--
bond, or a --NR.sup.9-- bond. Examples thereof include a cyclic
alkyl structure, a cyclic ester structure, a cyclic acid anhydride
structure, a cyclic amide structure, and a cyclic imide
structure.
[0080] In a case where at least two of R.sup.1 to R.sup.4 form a
cyclic alkyl structure through a --C-- bond, examples of the
structure include cyclopentyl and cyclohexyl. In a case where a
cyclic ester structure is formed through a --O-- bond, examples of
the structure include .gamma.-butyrolactone and
.delta.-valerolactone. In a case of a cyclic acid anhydride
structure, a maleic anhydride structure is exemplified. In a case
where a lactam ring is formed through a --NR.sup.9-- bond,
.gamma.-lactam and .delta.-lactam are exemplified. In a case where
a maleimide ring which is a lactam ring or a cyclic imide structure
is formed, R.sup.9 on a nitrogen atom may represent an alkyl group
having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon
atoms. Examples of the alkyl group having 1 to 10 carbon atoms
include a methyl group, an ethyl group, an n-propyl group, an
i-propyl group, an n-butyl group, a tert-butyl group, a
1-methylbutyl group, a 2-methylbutyl group, a n-pentyl group, a
1-methylpentyl group, a 1-ethylbutyl group, a 2-methylhexyl group,
a 2-ethylhexyl group, a 4-methylheptyl group, a cyclopentyl group,
a cyclohexyl group, and a cyclooctyl group. Examples of the aryl
group having 6 to 20 carbon atoms include phenyl, naphthyl,
anthracenyl, o-tolyl, m-tolyl, p-tolyl, biphenyl, and phenol.
[0081] Among these, it is preferable that R.sup.1 to R.sup.4 in
Formula (1) represent an alkoxycarbonyl group, an aryloxycarbonyl
group, an alkoxycarbonylalkyl group, an alkoxycarbonylaryl group,
an alkoxyalkyloxycarbonyl group, an alkoxycarbonylalkyloxycarbonyl
group, a .gamma.-butyrolactone ring, maleic anhydride, or a
maleimide ring.
[0082] Further, X.sub.1 indicates a structure derived from an
element selected from oxygen and sulfur. A structure derived from
oxygen is preferable. As described above, it is considered that the
material for forming an underlayer film according to the present
embodiment, which contains a cyclic olefin polymer having the
repeating structural unit [B] represented by Formula (2) in which
X.sub.1 satisfies the above-described definition, is capable of
exhibiting appropriate adhesiveness to the interface of the
substrate at the time of embedding the uneven structure of the
substrate, suppressing occurrence of voids and the like, and
realizing the embedding property in an excellent state while
maintaining high flatness. Further, the interaction with the
substrate due to the presence of elements such as oxygen and sulfur
in the main chain of the cyclic olefin polymer is assumed to become
a driving force for the cyclic olefin polymer to enter the fine
uneven structure.
[0083] The cyclic olefin polymer according to the present
embodiment may have two or more structural units in which at least
one of R.sup.1 to R.sup.4 in the repeating structural unit [A]
represented by Formula (1) is different from the rest.
[0084] In the repeating structural unit [A] represented by Formula
(1) according to the present embodiment, examples of the cyclic
olefin polymer in which n represents 0 include
poly(bicycle[2.2.1]hept-2-ene) in a case where all of R.sup.1 to
R.sup.4 represent hydrogen;
poly(5-methyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyl-bicyclo[2.2.1]hept-2-ene), and
poly(5-cyclooctyl-bicyclo[2.2.1]hept-2-ene) in a case where at
least one of R.sup.1 to R.sup.4 represents an alkyl group;
poly(5-phenyl-bicyclo[2.2.1]hept-2-ene),
poly(5-naphthyl-bicyclo[2.2.1]hept-2-ene),
poly(5-anthracenyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(o-tolyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(m-tolyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-p-tolyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-biphenyl-bicyclo[2.2.1]hept-2-ene), and
poly(5-(4-hydroxyphenyl)-bicyclo[2.2.1]hept-2-ene) in a case where
at least one of R.sup.1 to R.sup.4 represents an aryl group;
poly(5-methoxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxy)-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxy)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxy)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxy)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentoxy)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-cyclooctyloxy-bicyclo[2.2.1]hept-2-ene) in a case where at
least one of R.sup.1 to R.sup.4 represents an alkoxy group;
poly(5-phenyloxy-bicyclo[2.2.1]hept-2-ene),
poly(5-naphthyloxy-bicyclo[2.2.1]hept-2-ene),
poly(5-anthracenyloxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(o-tolyloxy)-bicyclo[2.2.1]hept-2-ene),
poly(5-(m-tolyloxy)-bicyclo[2.2.1]hept-2-ene),
poly(5-(p-tolyloxy)-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-oxy-1,1'-biphenyl)-bicyclo[2.2.1]hept-2-ene), and
(5-(4-hydroxyphenyloxy)-bicyclo[2.2.1]hept-2-ene) in a case where
at least one of R.sup.1 to R.sup.4 represents an aryloxy group;
poly(5-methoxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-methoxyethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxyethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxymethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-isopropoxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxymethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-isobutoxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxymethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxymethyl-bicyclo[2.2.1]hept-2-ene) in a case
where at least one of R.sup.1 to R.sup.4 represents an alkoxyalkyl
group; poly(5-phenyloxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-naphthyloxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-anthracenyloxymethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(o-tolyloxymethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(m-tolyloxymethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-p-tolyloxymethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-oxy-1,1'-biphenylmethyl)-bicyclo[2.2.1]hept-2-ene), and
poly(5-(4-hydroxyphenyloxymethyl)-bicyclo[2.2.1]hept-2-ene) in a
case where at least one of R.sup.1 to R.sup.4 represents an
aryloxyalkyl group;
poly(5-methoxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-isobutoxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-hexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3-dimethyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3,3-trimethyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-hexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethyl-3-hexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methylbutoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methylpentoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methylpentoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylpentoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-heptyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclopentylethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarboxyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclooctyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclooctyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-methyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-bic-
yclo[2.2.1]hept-2-ene),
poly(5-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-bicyclo[2.2.1]hept-2-ene), and
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-bicyclo[2.2.1]hept-2-ene) in a case where at least one of
R.sup.1 to R.sup.4 represents an alkoxycarbonyl group;
poly(5-dimethylaminocarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-diethylaminocarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethylmethylaminocarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-methylbutylaminocarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-butylethylaminocarbonyl-bicyclo[2.2.1]hept-2-ene), and
poly(5-cyclohexylmethylaminocarbonyl-bicyclo[2.2.1]hept-2-ene) in a
case where at least one of R.sup.1 to R.sup.4 represents a
dialkylaminocarbonyl group;
poly(5-phenoxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-benzyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylphenoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethylphenoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-naphthoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-naphthoxycarbonyl)-bicyclo[2.2.1]hept-2-ene), and
poly(5-(1-anthracenoxycarbonyl)-bicyclo[2.2.1]hept-2-ene) in a case
where at least one of R.sup.1 to R.sup.4 represents an
aryloxycarbonyl group;
poly(5-methylphenylaminocarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethylphenylaminocarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-butylphenylaminocarbonyl-bicyclo[2.2.1]hept-2-ene), and
poly(5-cyclohexylphenylaminocarbonyl-bicyclo[2.2.1]hept-2-ene) in a
case where at least one of R.sup.1 to R.sup.4 represents an
alkylarylaminocarbonyl group;
poly(5-methoxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-methoxycarbonylethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-butoxycarbonyl)methyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3-dimethyl-2-butoxycarbonyl)methyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-hexyloxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-octyloxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonyl)methyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-cyclopentyl-2-propoxycarbonyl)methyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-methylcyclopentyloxycarbonyl)methyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-ethylcyclopentyloxycarbonyl)methyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(1-methylcyclohexyloxycarbonyl)methyl)-bicyclo[2.2.1]hept-2-ene),
and
poly(5-(1-ethylcyclohexyloxycarbonyl)methyl)-bicyclo[2.2.1]hept-2-ene-
) in a case where at least one of R.sup.1 to R.sup.4 represents an
alkoxycarbonylalkyl group;
poly(5-methoxycarbonylphenyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylphenyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-(2-methyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-2,3-dimethyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(2-methyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-
-2-ene), poly(5-methoxycarbonylnaphthyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylnaphthyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(5-(l-ethylcyclopentyloxycarbonyl)naphthyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-bicyclo[2.2.1-
]hept-2-ene), and
poly(5-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-en-
e) in a case where at least one of R.sup.1 to R.sup.4 represents an
alkoxycarbonylaryl group;
poly(5-phenoxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-benzyloxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylphenoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethylphenoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-naphthoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-naphthoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene), and
poly(5-(1-anthracenoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene) in
a case where at least one of R.sup.1 to R.sup.4 represents an
aryloxycarbonylalkyl group;
poly(5-methoxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-isopropoxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-norbornyloxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-ethylcyclopentyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-methylcyclohexyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-ethylcyclohexyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-methylnorbornyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-ethylnorbornyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-ethoxypropyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethoxy-1-methylethyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-tetrahydrofuran-2-yloxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-
-ene),
poly(5-tetrahydropyran-2-yloxymethyloxycarbonyl-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-adamantyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-adamantyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-methoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-ethoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-propoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-isopropoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-butoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-tert-butoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclooctyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-norbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-tetrahydropyran-2-yloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-adamantyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene-
), and
poly(5-(1-(2-adamantyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene)
in a case where at least one of R
.sup.1 to R.sup.4 represents an alkoxyalkyloxycarbonyl group; and
poly(5-methoxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene)
poly(5-(n-propoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(isopropoxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl)-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl)-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl)-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-norbornyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(1-methylnorbornyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-ethylnorbornyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-ethoxypropyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-(2-(1-adamantyl)-2-propoxycarbonyl)ethoxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(3-(2-(1-adamantyl)-2-propoxycarbonyl)propoxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)-cyclopentyloxycarbonyl-
)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(5-1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-b-
icyclo[2.2.1]hept-2-ene),
poly(5-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(6-tert-butoxycarbonyl-tetrahydronaphthalene-2-yloxycarbonyl)-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodec-
ane-4-yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene), and
poly(5-(9-1-methylcyclohexyloxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.-
2,7]-dodecane-4-yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene) in a case
where at least one of R.sup.1 to R.sup.4 represents an
alkoxycarbonylalkyloxycarbonyl group.
[0085] In a case where R.sup.1 to R.sup.4 are bonded to one another
to form a ring structure, examples of the cyclic alkyl structure
include poly(1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene).
Examples of the cyclic ester structure which can form a lactone
ring include poly(4-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one)
as a .gamma.-butyrolactone structure;
poly(4-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one) as a
.delta.-valerolactone structure; and
poly(4-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione) as acyclic
acid anhydride structure. Examples of the cyclic amide structure
which can form a lactam ring include
poly(4-methyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-ethyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-(n-propyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-(n-butyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-(1-methylbutyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-cyclopentyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-cyclohexyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-phenyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one), and
poly(4-(4-hydroxyphenyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one)
as .gamma.-lactam; and
poly(4-methyl-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-ethyl-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-(n-propyl)-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-(n-butyl)-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-(1-methylbutyl)-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-cyclopentyl-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-cyclohexyl-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-phenyl-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
and
poly(4-(4-hydroxyphenyl)-4-aza-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one-
) as .delta.-lactam. Examples of the cyclic imide structure which
can form a maleimide ring include
poly(4-methyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(ethyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(n-propyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(n-butyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(1-methylbutyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione-
),
poly(4-cyclopentyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-cyclohexyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-phenyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-decene-3,5-dione)
and
poly(4-(4-hydroxyphenyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-
-dione).
[0086] Among these, in the repeating structural unit [A]
represented by Formula (1) according to the present embodiment, as
the cyclic olefin polymer in which n represents 0,
poly(5-methoxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-isobutoxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-hexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3-dimethyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3,3-trimethyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-2-methyl-2-hexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethyl-3-hexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methylbutoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methylpentoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methylpentoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylpentoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-heptyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclopentylethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclophexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclooctyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclooctyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-methyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-bic-
yclo[2.2.1]hept-2-ene),
poly(5-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-methoxycarbonylphenyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylphenyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-n-pentyloxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-(2-methyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-2,3-dimethyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(2-methyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-
-2-ene), poly(5-methoxycarbonylnaphthyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylnaphthyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-en-
e), poly(5-phenoxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-benzyloxycarbonylmethyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylphenoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethylphenoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-naphthoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-naphthoxycarbonylmethyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-anthracenoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-methoxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-isopropoxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxymethyloxycarbony-bicyclo[2.2.1]hept-2-ene),
poly(5-norbornyloxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-ethylcyclopentyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-methylcyclohexyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-ethylcyclohexyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-methylnorbornyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-ethylnorbornyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-ethoxypropyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethoxy-1-methylethyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-tetrahydrofuran-2-yloxymethyloxycarbonyl-bicyclo[2.2.1]hept-2-
-ene),
poly(5-tetrahydropyran-2-yloxymethyloxycarbonyl-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-adamantyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-adamantyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-methoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-ethoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-propoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-isopropoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-butoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-tert-butoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclooctyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-norbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-tetrahydropyran-2-yloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-adamantyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-(2-adamantyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl)-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl)-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl)-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-norbornyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(1-methylnorbornyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-ethylnorbornyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-ethoxypropyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-(2-(1-adamantyl)-2-propoxycarbonyl)ethoxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(3-(2-(1-adamantyl)-2-propoxycarbonyl)propoxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)-cyclopentyloxycarbonyl-
)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(5-1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-b-
icyclo[2.2.1]hept-2-ene),
poly(5-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(6-tert-butoxycarbonyl-tetrahydronaphthalene-2-yloxycarbonyl)-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodec-
ane-4-yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene), or
poly(5-(9-1-methylcyclohexyloxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.-
2,7]-dodecane-4-yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene) is
preferable.
[0087] Among these, from the viewpoints of improving the solubility
in a solvent (PGMEA) during preparation of a coating solution and
greatly changing the polarity of the cyclic olefin polymer after
application, in the repeating structural unit [A] represented by
Formula (1) according to the present embodiment, as the cyclic
olefin polymer in which n represents 0,
poly(5-(tert-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3-dimethyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3,3-trimethyl-2-butoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-2-methyl-2-hexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethyl-3-hexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-heptyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclopentylethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclooctyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclooctyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-methyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-bic-
yclo[2.2.1]hept-2-ene),
poly(5-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-(2-methyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-2,3-dimethyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(2-methyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylnaphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-bicyclo[2.2.
1]hept-2-ene),
poly(5-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(tert-butoxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-ethylcyclopentyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-methylcyclohexyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-ethylcyclohexyloxymethyloxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-(1-methoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-ethoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-propoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-isopropoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-butoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-tert-butoxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclooctyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-norbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2--
ene),
poly(5-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(1-tetrahydropyran-2-yloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-adamantyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-(2-adamantyloxy)ethoxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl)-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl)-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl)-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(1-(2-(1-adamantyl)-2-propoxycarbonyl)ethoxycarbonyl)-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(3-(2-(1-adamantyl)-2-propoxycarbonyl)propoxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)-cyclopentyloxycarbonyl-
)-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-bicyclo[2.2.1]hept--
2-ene),
poly(5-(5-1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-b-
icyclo[2.2.1]hept-2-ene),
poly(5-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene),
poly(5-(6-tert-butoxycarbonyl-tetrahydronaphthalene-2-yloxycarbonyl)-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodec-
ane-4-yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene), or
poly(5-(9-1-methylcyclohexyloxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.-
2,7]-dodecane-4-yloxycarbonyl)-bicyclo[2.2.1]hept-2-ene) is more
preferable.
[0088] In the repeating structural unit [A] represented by Formula
(1) according to the present embodiment, in a case where R.sup.1 to
R.sup.4 are bonded to one another to form a ring structure, as the
cyclic olefin polymer in which n represents 0,
poly(4-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-methyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(ethyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(n-propyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(n-butyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(1-methylbutyl)-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-di
one),
poly(4-cyclopentyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dio-
ne),
poly(4-cyclohexyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione)-
,
poly(4-phenyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
or
poly(4-(4-hydroxyphenyl-4-aza-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dion-
e) is preferable.
[0089] In the repeating structural unit [A] represented by Formula
(1) according to the present embodiment, examples of the cyclic
olefin polymer in which n represents 1 include
poly(tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene) in a case
where all of R.sup.1 to R.sup.4 represent hydrogen;
poly(8-methyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-ethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-propyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-i-propyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-n-butyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tert-butyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-pentyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
and
poly(8-cyclohexyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclooctyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)
in a case where at least one of R.sup.1 to R.sup.4 represents an
alkyl group;
poly(8-phenyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-naphthyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-anthracenyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(o-tolyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(m-tolyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(p-tolyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-biphenyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
and
poly(8-(4-hydroxyphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecen-
e) in a case where at least one of R.sup.1 to R.sup.4 represents an
aryl group;
poly(8-methoxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-ethoxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-propoxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(i-propoxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-butoxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-pentoxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclohexyloxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
and
poly(8-cyclooctyloxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecen-
e) in a case where at least one of R.sup.1 to R.sup.4 represents an
alkoxy group;
[0090]
poly(8-phenyloxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-naphthyloxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-anthracenyloxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(o-tolyloxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(m-tolyloxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(p-tolyloxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-oxy-1,1'-biphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene), and
(8-(4-hydroxyphenyloxy)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene-
) in a case where at least one of R.sup.1 to R.sup.4 represents an
aryloxy group;
poly(8-methoxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dode-
cene),
poly(8-methoxyethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-ethoxyethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-(n-propoxymethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-isopropoxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dode-
cene),
poly(8-(n-butoxymethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-do-
decene),
poly(8-isobutoxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene),
poly(8-tert-butoxymethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-cyclopentyloxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dode-
cene),
poly(8-cyclohexyloxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene), and
poly(8-cyclooctyloxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodec-
ene) in a case where at least one of R.sup.1 to R.sup.4 represents
an alkoxyalkyl group;
poly(8-phenyloxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-naphthyloxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-anthracenyloxymethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(o-tolyloxymethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(m-tolyloxymethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(p-tolyloxymethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-do-
decene),
poly(8-4-oxy-1,1'-biphenylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene), and
poly(8-(4-hydroxyphenyloxymethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene) in a case where at least one of R.sup.1 to R.sup.4
represents an aryloxyalkyl group;
poly(8-methoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-ethoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-(n-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dode-
cene),
poly(8-(n-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-isobutoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(tert-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(n-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(2-methyl-2-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(3-methyl-3-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-do-
decene),
poly(8-(n-hexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-cyclohexyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(2-methyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(2,3-dimethyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(2,3,3-trimethyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(2-methyl-2-hexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(3,4-dimethyl-3-hexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(3-methylbutoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(2-methylpentoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(3-methylpentoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(4-methylpentoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(3-methyl-3-heptyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(2-cyclopentyl)-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1,1-dicyclopentylethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-methylcyclooctyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-ethylcyclooctyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene), and
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene) in a case
where at least one of R.sup.1 to R.sup.4 represents an
alkoxycarbonyl group;
poly(8-dimethylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-diethylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-ethylmethylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-methylbutylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-butylethylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene), and
poly(8-cyclohexylmethylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene) in a case where at least one of R.sup.1 to R.sup.4
represents an alkylaminocarbonyl group;
poly(8-phenoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-benzyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(4-methylphenoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(3,4-dimethylphenoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1-naphthoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(2-naphthoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene), and
poly(8-(1-anthracenoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene) in a case where at least one of R.sup.1 to R.sup.4
represents an aryloxycarbonyl group;
poly(8-methylphenylaminocarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-ethylphenylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-butylphenylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene), and
poly(8-cyclohexylphenylaminocarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene) in a case where at least one of R.sup.1 to R.sup.4
represents an alkylarylaminocarbonyl group;
poly(8-methoxycarbonylmethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-methoxycarbonylethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-ethoxycarbonylmethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dode-
cene),
poly(8-ethoxycarbonylethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(n-propoxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(i-propoxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(n-butoxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(tert-butoxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(2-methyl-2-butoxycarbonyl)methyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(2,3-dimethyl-2-butoxycarbonyl)methyl)-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonylmethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(n-hexyloxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-cyclohexyloxycarbonylmethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(n-octyloxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-cyclooctyloxycarbonylmethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(2-cyclopentyl-2-propoxycarbonyl)methyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonyl)methyl)-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonyl)methyl)-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonyl)methyl)-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonyl)methyl)-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene), and
poly(8-(1-ethylcyclohexyloxycarbonyl)methyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene) in a case where at least one of R.sup.1 to
R.sup.4 represents an alkoxycarbonylalkyl group;
poly(8-methoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-do-
decene),
poly(8-ethoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(n-propoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(i-propoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(n-butoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(tert-butoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(3-(2-methyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,51.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-methyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-methoxycarbonylnaphthyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene),
poly(8-ethoxycarbonylnaphthyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(n-propoxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(i-propoxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(n-butoxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(n-pentyloxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene), and
poly(8-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene) in a case where at least one of R.sup.1
to R.sup.4 represents an alkoxycarbonylaryl group;
poly(8-phenoxycarbonylmethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-benzyloxycarbonylmethyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(4-methylphenoxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(3,4-dimethylphenoxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(1-naphthoxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(2-naphthoxycarbonylmethyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene), and
poly(8-(1-anthracenoxycarbonylmethyl)-tetracyclo[4.4.0.1
.sup.2,5.1.sup.7,10]-3-dodecene) in a case where at least one of
R.sup.1 to R.sup.4 represents an aryloxycarbonylalkyl group;
poly(8-(methoxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(ethoxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(n-propoxymethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-isopropoxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(n-butoxymethyloxycarbony)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-(tert-butoxymethyloxycarbony)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-cyclopentyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-cyclohexyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-cyclooctyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-norbornyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1-methylcyclopentyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(1-methylnorbornyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(1-ethylnorbornyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(1-ethoxypropyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.
1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxy-1-methylethyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydrofuran-2-yloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydropyran-2-yloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-adamantyloxymethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-adamantyloxymethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-(1-methoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1-(1-ethoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(1-(1-n-propoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-(1-isopropoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-(1-n-butoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-(1-tert-butoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-(1-cyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(1-(1-cyclooctyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(1-(1-norboryloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydropyran-2-yloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-adamantyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene), and
poly(8-(1-(2-adamantyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene) in a case where at least one of R.sup.1 to
R.sup.4 represents an alkoxyalkyloxycarbonyl group; and
poly(8-methoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-ethoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(n-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-isopropoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxy-
carbonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene)
poly(8-cyclohexyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene)
poly(8-cyclooctyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-norbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylnorbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylnorbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxypropyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-1-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-(1-adamantyl)-2-propoxycarbonyl)-ethoxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-(1-adamantyl)-2-propoxycarbonyl)-propoxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)-cyclopentyloxycarbonyl)-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(6-tert-butoxycarbonyl-decahydronaphthalene-2-yloxycarbonyl)-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodec-
ane-4-yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
and
poly(8-(9-(1-methylcyclohexyloxycarbonyl)-tetracyclo[6.2.1.1.sup.3,6.-
0.sup.2,7]-dodecane-4-yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene) in a case where at least one of R.sup.1 to R.sup.4
represents an alkoxycarbonylalkyloxycarbonyl group.
[0091] In a case where R.sup.1 to R.sup.4 are bonded to each other
to form a ring structure, examples of the cyclic alkyl structure
include
poly(1,4,4a,5,6,7,8,8a,9,9a,10,10a-dodecahydro-1,4:9,10-dimethano-anthrac-
ene). Examples of the cyclic ester structure which can form a
lactone ring include
poly(4-oxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-pe-
ntadecene-3-one) as a .gamma.-butyrolactone structure; and
poly(4-oxy-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.9,14]-11-hexadecen-
e-3-one) as a .delta.-valerolactone structure. Examples of the
cyclic acid anhydride structure include
poly(4-oxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-pentadecen-
e-3-one). Examples of the cyclic amide structure which can form a
lactam ring include
poly(4-methyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3-one),
poly(4-ethyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-pe-
ntadecene-3-one),
poly(4-(n-propyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]--
10-pentadecene-3-one),
poly(4-(n-butyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-1-
0-pentadecene-3-one),
poly(4-(1-methylbutyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8-
,13]-10-pentadecene-3-one),
poly(4-cyclopentyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-
-10-pentadecene-3-one),
poly(4-cyclohexyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]--
10-pentadecene-3-one),
poly(4-phenyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3-one), and
poly(4-(4-hydrophenyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8-
,13]-10-pentadecene-3-one) as .gamma.-lactam; and
poly(4-methyl-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.9,14]-11--
hexadecene-3-one),
poly(4-methyl-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.9,14]-11--
hexadecene-3-one),
poly(4-(n-propyl)-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.9,14]-
-11-hexadecene-3-one),
poly(4-(n-butyl)-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.9,14]--
11-hexadecene-3-one),
poly(4-(1-methylbutyl)-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.-
9,14]-11-hexadecene-3-one),
poly(4-cyclopentyl-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.9,14-
]-11-hexadecene-3-one),
poly(4-cyclohexyl-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.9,14]-
-11-hexadecene-3-one),
poly(4-phenyl-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.sup.9,14]-11--
hexadecene-3-one), and
poly(4-(4-hydroxyphenyl)-4-aza-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.su-
p.9,14]-11-hexadecene-3-one) as .delta.-lactam. Examples of the
cyclic imide structure which can form a maleimide ring include
poly(4-methyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3,5-dione),
poly(4-ethyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-pe-
ntadecene-3,5-dione),
poly(4-(n-propyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]--
10-pentadecene-3,5-dione),
poly(4-(n-butyl)-4-aza-pentacyclo[9.2.1.1.sup.1.0.sup.2,6.0.sup.8,13]-10--
pentadecene-3,5-dione),
poly(4-(1-methylbutyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8-
,13]-10-pentadecene-3,5-dione),
poly(4-cyclopentyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13-
]-10-pentadecene-3,5-dione),
poly(4-cyclohexyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]--
10-pentadecene-3,5-dione),
poly(4-phenyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3,5-dione), and
poly(4-(4-hydroxyphenyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup-
.8,13]-10-pentadecene-3,5-dione). Among these, in the repeating
structural unit [A] represented by Formula (1) according to the
present embodiment, as the cyclic olefin polymer in which n
represents 1,
poly(8-methoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-ethoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-(n-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dode-
cene),
poly(8-(n-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-isobutoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(tert-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(n-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(2-methyl-2-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(3-methyl-3-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-do-
decene),
poly(8-(n-hexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-cyclohexyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(2-methyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(2,3-dimethyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(2,3,3-trimethyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(2-methyl-2-hexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(3,4-dimethyl-3-hexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(3-methylbutoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(2-methylpentoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(3-methylpentoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(4-methylpentoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(3-methyl-3-heptyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(2-cyclopentyl)-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene,
poly(8-(2-cyclohexyl-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1,1-dicyclopentylethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-methylcyclooctyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-ethylcyclooctyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-methoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-do-
decene),
poly(8-ethoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(n-propoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(i-propoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(n-butoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(tert-butoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(3-(2-methyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-methyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-methoxycarbonylnaphthyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene),
poly(8-ethoxycarbonylnaphthyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(n-propoxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(i-propoxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(n-butoxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(n-pentyloxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-phenoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-benzyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(4-methylphenoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(3,4-dimethylphenoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1-naphthoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(2-naphthoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(1-anthracenoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(methoxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(ethoxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(n-propoxymethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-isopropoxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(n-butoxymethyloxycarbony)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-(tert-butoxymethyloxycarbony)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-cyclopentyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-cyclohexyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-cyclooctyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-norbornyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1-methylcyclopentyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(1-methylnorbornyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(1-ethylnorbornyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(1-ethoxypropyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(1-ethoxy-1-methylethyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydrofuran-2-yloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydropyran-2-yloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-adamantyloxymethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-adamantyloxymethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-(1-methoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1-(1-ethoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(1-(1-n-propoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-(1-isopropoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-(1-n-butoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-(1-tert-butoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-(1-cyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(1-(1-cyclooctyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(1-(1-norboryloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydropyran-2-yloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-adamantyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(1-(2-adamantyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxy-
carbonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-cyclohexyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-cyclooctyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-norbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene,
poly(8-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylnorbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylnorbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxypropyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-1-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-(1-adamantyl)-2-propoxycarbonyl)-ethoxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-(1-adamantyl)-2-propoxycarbonyl)-propoxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)-cyclopentyloxycarbonyl)-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(6-tert-butoxycarbonyl-decahydronaphthalene-2-yloxycarbonyl)-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodec-
ane-4-yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
or
poly(8-(9-(1-methylcyclohexyloxycarbonyl)-tetracyclo[6.2.1.1.sup.3,6.0-
.sup.2,7]-dodecane-4-yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene is preferable.
[0092] Among these, from the viewpoints of improving the solubility
in a solvent (PGMEA) during preparation of a coating solution and
greatly changing the polarity of the cyclic olefin polymer after
application, in the repeating structural unit [A] represented by
Formula (1) according to the present embodiment, as the cyclic
olefin polymer in which n represents 0,
poly(8-(tert-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(2-methyl-2-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3-methyl-3-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(2,3-dimethyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(2,3,3-trimethyl-2-butoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(2-methyl-2-hexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(3,4-dimethyl-3-hexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.25.1.sup.-
7,10]-3-dodecene),
poly(8-(3-methyl-3-heptyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(2-cyclopentyl)-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1,1-dicyclopentylethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-methylcyclooctyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-ethylcyclooctyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7 1.sup.0]-3-dodecene),
poly(8-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(3-(2-methyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-methyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(n-pentyloxycarbonylnaphthyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxymethyloxycarbony)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1-methylcyclopentyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxymethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1-(1-ethoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(1-(1-n-propoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(1-(1-isopropoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(1-(1-n-butoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(1-(1-tert-butoxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-(1-cyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,51.su-
p.7,10]-3-dodecene),
poly(8-(1-(1-cyclooctyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-(1-(1-norboryloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydropyran-2-yloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-adamantyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(1-(2-adamantyloxy)ethoxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)-
,
poly(8-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxy-
carbonylmethyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-(1-adamantyl)-2-propoxycarbonyl)-ethoxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-(1-adamantyl)-2-propoxycarbonyl)-propoxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)-cyclopentyloxycarbonyl)-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(6-tert-butoxycarbonyl-decahydronaphthalene-2-yloxycarbonyl)-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodec-
ane-4-yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
or
poly(8-(9-(1-methylcyclohexyloxycarbonyl)-tetracyclo[6.2.1.1.sup.3,6.0-
.sup.2,7]-dodecane-4-yloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene is more preferable.
[0093] In the repeating structural unit [A] represented by Formula
(1) according to the present embodiment, in a case where R.sup.1 to
R.sup.4 are bonded to one another to form a ring structure, as the
cyclic olefin polymer in which n represents 1,
poly(4-oxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-pentadecen-
e-3-one),
poly(4-oxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3,5-dione),
poly(4-methyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3,5-dione),
poly(4-ethyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-pe-
ntadecene-3,5-dione),
poly(4-(n-propyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]--
10-pentadecene-3,5-dione),
poly(4-(n-butyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-1-
0-pentadecene-3,5-dione),
poly(4-(1-methylbutyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8-
,13]-10-pentadecene-3,5-dione),
poly(4-cyclopentyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13-
]-10-penta decene-3,5-dione),
poly(4-cyclohexyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]--
10-pentadecene-3,5-dione),
poly(4-phenyl-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3,5-dione), or
poly(4-(4-hydroxyphenyl)-4-aza-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup-
.8,13]-10-pentadecene-3,5-dione) is preferable.
[0094] R.sup.5 to R.sup.8 in Formula (2) each have the same
definition as that for R.sup.1 to R.sup.4 in Formula (1). Further,
R.sup.5 to R.sup.8 may form a ring structure. Specifically, R.sup.5
to R.sup.8 are each independently bonded to one another or at least
two of these are bonded to each other to form a ring structure
optionally through a --C-- bond, a --O-- bond, or a --NR.sup.9--
bond. Examples thereof include a cyclic alkyl structure, a cyclic
ester structure, a cyclic acid anhydride structure, a cyclic amide
structure, and a cyclic imide structure.
[0095] The cyclic olefin polymer according to the present
embodiment may have two or more structural units in which at least
one of R.sup.5 to R.sup.8 in the repeating structural unit [B]
represented by Formula (2) is different from the rest.
[0096] In the repeating structural unit [B] represented by Formula
(2) according to the present embodiment, examples of the cyclic
olefin polymer in which n represents 0 include
poly(5-methyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyl-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-cyclooctyl-7-oxy-bicyclo[2.2.1]hept-2-ene) in a case where
at least one of R.sup.5 to R.sup.8 represents an alkyl group;
poly(5-phenyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-naphthyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-anthracenyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(o-tolyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(m-tolyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(p-tolyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-biphenyl-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-(4-hydroxyphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene) in a case
where at least one of R.sup.5 to R.sup.8 represents an aryl group;
poly(5-methoxy-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxy-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxy)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxy)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxy)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxy)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentoxy)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxy-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxy-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-cyclopentyloxy-7-oxy-bicyclo[2.2.1]hept-2-ene) in a case
where at least one of R.sup.5 to R.sup.8 represents an alkoxy
group; poly(5-phenyloxy-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-naphthyloxy-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-anthracenyloxy-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(o-tolyloxy)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(m-tolyloxy)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(p-tolyloxy)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-oxy-1,1'-biphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-(4-hydroxyphenyloxy)-7-oxy-bicyclo[2.2.1]hept-2-ene) in a
case where at least one of R.sup.5 to R.sup.8 represents an aryloxy
group; poly(5-methoxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-methoxyethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxyethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxymethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-isopropoxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxymethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-isobutoxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxymethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-cyclooctyloxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene) in a
case where at least one of R.sup.5 to R.sup.8 represents an
alkoxyalkyl group;
poly(5-phenyloxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-naphthyloxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-anthracenyloxymethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(o-tolyloxymethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(m-tolyloxymethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(p-tolyloxymethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-oxy-1,1'-biphenylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-hydroxyphenyloxymethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
in a case where at least one of R.sup.5 to R.sup.8 represents an
aryloxyalkyl group;
poly(5-methoxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-isobutoxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2--
ene),
poly(5-cyclopentyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-hexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3-dimethyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3,3-trimethyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-methyl-2-hexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethyl-3-hexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methylbutoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methylpentoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methylpentoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylpentoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-heptyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclopentylethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclooctyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclooctyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-methyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene) in a case where at least one
of R.sup.5 to R.sup.8 represents an alkoxycarbonyl group;
poly(5-dimethylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-diethylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethylmethylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-methylbutylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-butylethylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-cyclohexylmethylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene)
in a case where at least one of R.sup.5 to R.sup.8 represents a
dialkylaminocarbonyl group;
poly(5-phenoxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-benzyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylphenoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethylphenoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-naphthoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-naphthoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-(1-anthracenoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene) in
a case where at least one of R.sup.5 to R.sup.8 represents an
aryloxycarbonyl group;
poly(5-methylphenylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethylphenylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-butylphenylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
and
poly(5-cyclohexylphenylaminocarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene)
in a case where at least one of R.sup.5 to R.sup.8 represents an
alkylarylaminocarbonyl group;
poly(5-methoxycarbonylmethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-methoxycarbonylethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylmethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-butoxycarbonyl)methyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2,3-dimethyl-2-butoxycarbonyl)methyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-cyclopentyloxycarbonylmethyl-7-oxy-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(n-hexyloxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxycarbonylmethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-octyloxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxycarbonylmethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonyl)methyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonyl)methyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonyl)methyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(1-ethylcyclopentyloxycarbonyl)methyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonyl)methyl)-7-oxy-bicyclo[2.2.1]hept-2--
ene), and
poly(5-(1-ethylcyclohexyloxycarbonyl)methyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene) in a case where at least one of R.sup.5 to R.sup.8
represents an alkoxycarbonylalkyl group;
poly(5-methoxycarbonylphenyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylphenyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-(2-methyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-(2-methyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-methoxycarbonylnaphthyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylnaphthyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene), and
poly(5-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene) in a case where at least one of R.sup.5 to R.sup.8
represents an alkoxycarbonylaryl group;
poly(5-phenoxycarbonylmethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-benzyloxycarbonylmethyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylphenoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethylphenoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-naphthoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-naphthoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
and
poly(5-(1-anthracenoxycarbonylmethyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)
in a case where at least one of R.sup.5 to R.sup.8 represents an
aryloxycarbonylalkyl group;
poly(5-methoxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-isopropoxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-norbornyloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-ethylcyclopentyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-ethylcyclohexyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-methylnorbornyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(1-ethylnorbornyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(1-ethoxypropyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-ethoxy-1-methylethyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-tetrahydrofuran-2-yloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-tetrahydropyran-2-yloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-adamantyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-adamantyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-methoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-ethoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-propoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-isopropoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-butoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-tert-butoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-(1-cyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2--
ene),
poly(5-(1-(1-cyclooctyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-norbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1-tetrahydropyran-2-yloxy)ethoxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(1-(1-adamantyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)-
, and
poly(5-(1-(2-adamantyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene) in a case where at least one of R
.sup.5 to R.sup.8 represents an alkoxyalkyloxycarbonyl group; and
poly(5-methoxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(isopropoxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(n-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(tert-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-cyclopentyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-cyclohexyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-cyclooctyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2--
ene),
poly(5-norbornyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-7-oxy-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-methylnorbornyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-ethylnorbornyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-ethoxypropyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1-(2-(1-adamantyl)-2-propoxycarbonyl)ethoxycarbonyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(3-(2-(1-adamantyl)-2-propoxycarbonyl)propoxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-7-oxy-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)-cyclopentyloxycarbonyl)-7-oxy-b-
icyclo[2.2.1]hept-2-ene),
poly(5-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(5-(1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-b-
icyclo[2.2.1]hept-2-ene),
poly(5-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(6-tert-butoxycarbonyl-tetrahydronaphthalene-2-yloxycarbonyl)-7-ox-
y-bicyclo[2.2.1]hept-2-ene),
poly(5-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodec-
ane-4-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-(9-(1-methylcyclohexyloxycarbonyl)-tetracyclo[6.2.1.1.sup.3,6.0.su-
p.2,7]-dodecane-4-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene) in
a case where at least one of R.sup.5 to R.sup.8 represents an
alkoxycarbonylalkyloxycarbonyl group.
[0097] In a case where R.sup.5 to R.sup.8 are bonded to one another
to form a ring structure, examples of the cyclic alkyl structure
include poly(1,4,4a,5,6,7,8,8a-octahydro-1,4-ethano-naphthalene).
Examples of the cyclic ester structure which can form a lactone
ring include
poly(4,10-dioxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one) as a
.gamma.-butyrolactone structure;
poly(4,10-dioxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one) as a
.delta.-valerolactone structure; and
poly(4,10-dioxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione) as a
cyclic acid anhydride structure. Examples of the cyclic amide
structure which can form a lactam ring include
poly(4-methyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-ethyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-(n-propyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4-(n-butyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one
poly(4-(1-methylbutyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3--
one),
poly(4-cyclopentyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-
-one),
poly(4-cyclohexyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-
-one),
poly(4-phenyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one-
), and
poly(4-(4-hydroxyphenyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-d-
ecene-3-one) as .gamma.-lactam;
poly(4-methyl-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-ethyl-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one),
poly(4-(n-propyl)-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-one-
),
poly(4-(n-butyl)-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3-on-
e),
poly(4-cyclobutyl-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-3--
one),
poly(4-cyclopentyl-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-
-3-one),
poly(4-cyclohexyl-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undece-
ne-3-one),
poly(4-phenyl-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecene-
-3-one), and
poly(4-(4-hydroxyphenyl)-4-aza-10-oxy-tricyclo[6.2.1.0.sup.2,7]-9-undecen-
e-3-one) as .delta.-lactam. Examples of the cyclic imide structure
which can form a maleimide ring include
poly(4-methyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(ethyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-(n-propyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dio-
ne),
poly(4-(n-butyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5--
dione),
poly(4-cyclobutyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene--
3,5-dione),
poly(4-cyclopentyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-di-
one),
poly(4-cyclohexyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,-
5-dione),
poly(4-phenyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,-
5-dion e), and
poly(4-(4-hydroxyphenyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene--
3,5-dione).
[0098] Among these, in the repeating structural unit [B]
represented by Formula (2) according to the present embodiment, as
the cyclic olefin polymer in which n represents 0,
poly(5-methoxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-isobutoxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2--
ene),
poly(5-cyclopentyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-hexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3-dimethyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3,3-trimethyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-methyl-2-hexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethyl-3-hexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methylbutoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methylpentoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methylpentoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylpentoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-heptyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclopentylethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclooctyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclooctyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-methyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene), and
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-methoxycarbonylphenyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylphenyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-(2-methyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-2,3-dimethyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-(2-methyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-methoxycarbonylnaphthyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxycarbonylnaphthyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(i-propoxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene), poly(5-phenoxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-benzyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-methylphenoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethylphenoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-naphthoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-naphthoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-anthracenoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-methoxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-ethoxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-propoxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-isopropoxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-butoxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclopentyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclohexyloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-cyclooctyloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-norbornyloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-ethylcyclopentyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-ethylcyclohexyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-methylnorbornyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(1-ethylnorbornyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(1-ethoxypropyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-ethoxy-1-methylethyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-tetrahydrofuran-2-yloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-tetrahydropyran-2-yloxymethyloxycarbonyl-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-adamantyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-adamantyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-methoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-ethoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-propoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-isopropoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-butoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-tert-butoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-(1-cyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2--
ene),
poly(5-(1-(1-cyclooctyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-norbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1-tetrahydropyran-2-yloxy)ethoxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(1-(1-adamantyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(1-(2-adamantyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(n-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(tert-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy--
bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-cyclopentyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-cyclohexyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-cyclooctyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hept-2--
ene),
poly(5-norbornyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-7-oxy-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-methylnorbornyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-ethylnorbornyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-ethoxypropyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1-(2-(1-adamantyl)-2-propoxycarbonyl)ethoxycarbonyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(3-(2-(1-adamantyl)-2-propoxycarbonyl)propoxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-7-oxy-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)-1-cyclopentyloxycarbonyl)-7-oxy-
-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(5-(1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-b-
icyclo[2.2.1]hept-2-ene),
poly(5-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(6-tert-butoxycarbonyl-tetrahydronaphthalene-2-yloxycarbonyl)-7-ox-
y-bicyclo[2.2.1]hept-2-ene),
poly(5-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1
.sup.3,6.0.sup.2,7]-dodecane-4-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-e-
ne), or
poly(5-(9-(1-methylcyclohexyloxycarbonyl)-tetracyclo[6.2.1.1.sup.3-
,6.0.sup.2,7]-dodecane-4-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)
is preferable.
[0099] Among these, from the viewpoints of improving the solubility
in a solvent (PGMEA) during preparation of a coating solution and
greatly changing the polarity of the cyclic olefin polymer after
application, in the repeating structural unit [B] represented by
Formula (2) according to the present embodiment, as the cyclic
olefin polymer in which n represents 0,
poly(5-(tert-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2--
ene),
poly(5-(2-methyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3-dimethyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,3,3-trimethyl-2-butoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(2-methyl-2-hexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3,4-dimethyl-3-hexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-methyl-3-heptyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclopentylethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methylcyclooctyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-ethylcyclooctyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(2-methyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(3-(2-methyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-(2-methyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-2-e-
ne),
poly(5-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(tert-butoxycarbonylphenyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(n-pentyloxycarbonylnaphthyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]-
hept-2-ene),
poly(5-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-7-oxy-bicyclo[2.2.1]hep-
t-2-ene),
poly(5-(tert-butoxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(1-methylcyclopentyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-methylcyclohexyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxymethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(1-(1-methoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(1-(1-ethoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-propoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-isopropoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-n-butoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-tert-butoxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1-(1-cyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-en-
e),
poly(5-(1-(1-cyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2--
ene),
poly(5-(1-(1-cyclooctyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-norbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-
-2-ene),
poly(5-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-
-ene),
poly(5-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]he-
pt-2-ene),
poly(5-(1-tetrahydropyran-2-yloxy)ethoxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(1-(1-adamantyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene)-
,
poly(5-(1-(2-adamantyloxy)ethoxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene-
),
poly(5-(tert-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept--
2-ene),
poly(5-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2-
.2.1]hept-2-ene),
poly(5-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.2.-
1]hept-2-ene),
poly(5-(1-(2-(1-adamantyl)-2-propoxycarbonyl)ethoxycarbonyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(3-(2-(1-adamantyl)-2-propoxycarbonyl)propoxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-7-oxy-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-bicyclo[2.2.1]h-
ept-2-ene),
poly(5-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-7-oxy-bicy-
clo[2.2.1]hept-2-ene),
poly(5-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[2.-
2.1]hept-2-ene),
poly(5-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-7-oxy-bicycl-
o[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-7-oxy-bicyclo[-
2.2.1]hept-2-ene),
poly(5-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-7-oxy-bicyc-
lo[2.2.1]hept-2-ene),
poly(5-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-7-oxy-bicyclo[2.2-
.1]hept-2-ene),
poly(5-(3-(1-methylcyclohexyloxycarbonyl)-cyclopentyloxycarbonyl)-7-oxy-b-
icyclo[2.2.1]hept-2-ene),
poly(5-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-7-oxy-bicyclo[2.2.1-
]hept-2-ene),
poly(5-(5-1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-bi-
cyclo[2.2.1]hept-2-ene),
poly(5-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-7-oxy-bicyclo-
[2.2.1]hept-2-ene),
poly(5-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene),
poly(5-(6-tert-butoxycarbonyl-tetrahydronaphthalene-2-yloxycarbonyl)-7-ox-
y-bicyclo[2.2.1]hept-2-ene),
poly(5-(9-tert-butoxycarbonyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodec-
ane-4-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene), or
poly(5-(9-(1-methylcyclohexyloxycarbonyl)-tetracyclo[6.2.1.1.sup.3,6.0.su-
p.2,7]-dodecane-4-yloxycarbonyl)-7-oxy-bicyclo[2.2.1]hept-2-ene) is
more preferable.
[0100] Further, in the repeating structural unit [B] represented by
Formula (2) according to the present embodiment, in a case where
R.sup.5 to R.sup.8 are bonded to one another to form a ring
structure, as the cyclic olefin polymer in which n represents 0,
poly(4,10-dioxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one),
poly(4,10-dioxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-methyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione),
poly(4-ethyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione
poly(4-(n-propyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dio-
ne),
poly(4-(n-butyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5--
dione),
poly(4-cyclobutyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene--
3,5-dione),
poly(4-cyclopentyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-di-
one),
poly(4-cyclohexyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,-
5-dione),
poly(4-phenyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,-
5-dione), or
poly(4-(4-hydroxyphenyl)-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene--
3,5-dione) is preferable.
[0101] In the repeating structural unit [B] represented by Formula
(2) according to the present embodiment, examples of the cyclic
olefin polymer in which n represents 1 include
poly(8-methyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-ethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(n-propyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(i-propyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-do-
decene),
poly(8-(n-butyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(tert-butyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(n-pentyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-cyclopentyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene),
poly(8-cyclohexyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene), and
poly(8-cyclooctyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-do-
decene) in a case where at least one of R.sup.5 to R.sup.8
represents an alkyl group;
poly(8-phenyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-naphthyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-anthracenyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(o-tolyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-(m-tolyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(p-tolyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-biphenyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene), and
poly(8-(4-hydroxyphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene) in a case where at least one of R.sup.5 to R.sup.8
represents an aryl group;
poly(8-methoxy-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodec-
ene),
poly(8-ethoxy-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene),
poly(8-(n-propoxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(i-propoxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene),
poly(8-(n-butoxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(tert-butoxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-(n-pentoxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene),
poly(8-cyclopentyloxy-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-cyclohexyloxy-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene), and
poly(8-cyclooctyloxy-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene) in a case where at least one of R.sup.5 to R.sup.8
represents an alkoxy group;
poly(8-phenyloxy-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dod-
ecene),
poly(8-naphthyloxy-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-anthracenyloxy-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-(o-tolyloxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(m-tolyloxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(p-tolyloxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-(4-oxy-1,1'-biphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene), and
poly(8-(4-hydroxyphenyloxy)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene) in a case where at least one of R.sup.5 to
R.sup.8 represents an aryloxy group;
poly(8-methoxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-
-dodecene),
poly(8-methoxyethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3--
dodecene),
poly(8-ethoxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-ethoxyethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-d-
odecene),
poly(8-(n-propoxymethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-isopropoxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-(n-butoxymethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10-
]-3-dodecene),
poly(8-isobutoxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(tert-butoxymethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-cyclopentyloxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-cyclohexyloxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene), and
poly(8-cyclooctyloxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene) in a case where at least one of R.sup.5 to R.sup.8
represents an alkoxyalkyl group;
poly(8-phenyloxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-naphthyloxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-anthracenyloxymethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-(o-tolyloxymethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(m-tolyloxymethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(p-tolyloxymethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-(4-oxy-1,1'-biphenylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene), and
poly(8-(4-hydroxyphenyloxymethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,51-
.sup.7,10]-3-dodecene) in a case where at least one of R.sup.5 to
R.sup.8 represents an aryloxyalkyl group;
poly(8-methoxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-ethoxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-(n-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(n-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-isobutoxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(tert-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-methyl-2-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-methyl-3-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(n-hexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-cyclohexyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-methyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(2,3-dimethyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2,3,3-trimethyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-hexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3,4-dimethyl-3-hexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-methylbutoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(2-methylpentoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3-methylpentoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(4-methylpentoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3-methyl-3-heptyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl)-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclopentylethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclooctyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclooctyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
and
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-ylox-
ycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene)
in a case where at least one of R.sup.5 to R.sup.8 represents an
alkoxycarbonyl group;
(5-dimethylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(5-diethylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(5-ethylmethylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(5-methylbutylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(5-butylethylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene), and
poly(5-cyclohexylmethylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene) in a case where at least one of R.sup.5
to R.sup.8 represents an alkylaminocarbonyl group;
poly(8-phenoxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-benzyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(4-methylphenoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3,4-dimethylphenoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-naphthoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-naphthoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene), and
poly(8-(1-anthracenoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene) in a case where at least one of R.sup.5 to
R.sup.8 represents an aryloxycarbonyl group;
poly(8-methylphenylaminocarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-ethylphenylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-butylphenylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene), and
poly(8-cyclohexylphenylaminocarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene) in a case where at least one of R.sup.1
to R.sup.4 represents an alkylarylaminocarbonyl group;
poly(8-methoxycarbonylmethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-methoxycarbonylethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-ethoxycarbonylmethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-ethoxycarbonylethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(n-propoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(i-propoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-butoxycarbonyl)methyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2,3-dimethyl-2-butoxycarbonyl)methyl)-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonylmethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(n-hexyloxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-cyclohexyloxycarbonylmethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-octyloxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-cyclooctyloxycarbonylmethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-propoxycarbonyl)methyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonyl)methyl)-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonyl)methyl)-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonyl)methyl)-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonyl)methyl)-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene), and
poly(8-(1-ethylcyclohexyloxycarbonyl)methyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene) in a case where at least one of
R.sup.5 to R.sup.8 represents an alkoxycarbonylalkyl group;
poly(8-methoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-ethoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-propoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(i-propoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-methyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-methyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-methoxycarbonylnaphthyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.
1.sup.7,10]-3-dodecene),
poly(8-ethoxycarbonylnaphthyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(n-propoxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(i-propoxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-11,12-dioxy-tetracycl-
o[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-11,12-dioxy-tetracycl-
o[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene), and
poly(8-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene) in a case where at least
one of R.sup.5 to R.sup.8 represents an alkoxycarbonylaryl group;
poly(8-phenoxycarbonylmethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-benzyloxycarbonylmethyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.
1.sup.7,10]-3-dodecene),
poly(8-(4-methylphenoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3,4-dimethylphenoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-naphthoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(2-naphthoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene), and
poly(8-(1-anthracenoxycarbonylmethyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene) in a case where at least one of R.sup.5
to R.sup.8 represents an aryloxycarbonylalkyl group;
poly(8-(methoxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(ethoxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(n-propoxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-isopropoxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-butoxymethyloxycarbony)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclohexyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclooctyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-norbornyloxymnethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxymnethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxymnethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxymnethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylnorbornyloxymnethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylnorbornyloxymnethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxypropyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxy-1-methylethyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydrofuran-2-yloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydropyran-2-yloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-adamantyloxymnethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-adamantyloxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-n-propoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-isopropoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-n-butoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-tert-butoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclooctyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-norboryloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydropyran-2-yloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-adamantyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene), and
poly(8-(1-(2-adamantyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene) in a case where at least one of
R.sup.5 to R.sup.8 represents an alkoxyalkyloxycarbonyl group; and
poly(8-methoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-ethoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-isopropoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetr-
acyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tet-
racyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetr-
acyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclohexyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclooctyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-norbornyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylnorbornyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylnorbornyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxypropyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetracycl-
o[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-(1-adamantyl)-2-propoxycarbonyl)-ethoxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-(1-adamantyl)-2-propoxycarbonyl)-propoxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-11,12-di-
oxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tet-
racyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetr-
acyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy--
tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10
]-3-dodecene),
poly(8-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)-1-cyclopentyloxycarbonyl)-11,12-
-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-11,12-d-
ioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(6-tert-butoxycarbonyl-decahydronaphthalene-2-yloxycarbonyl)-1-
1,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(9-tert-butoxycarbonyl-11,12-dioxy-tetracyclo[6.2.1.1.sup.3,6.0.su-
p.2,7]-dodecane-4-yloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene), and
poly(8-(9-(1-methylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo[6.2.1.1.-
sup.3,6.0.sup.2,7]-dodecane-4-yloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene) in a case where at least one of
R.sup.5 to R.sup.8 represents an alkoxycarbonylalkyloxycarbonyl
group.
[0102] In a case where R.sup.5 to R.sup.8 are bonded to each other
to form a ring structure, examples of the cyclic alkyl structure
include
poly(1,4,4a,5,6,7,8,8a,9,9a,10,10a-dodecahydro-1,4:9,10-diepoxy-naphthale-
ne). Examples of the cyclic ester structure which can form a
lactone ring include
poly(4,14,15-trioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,-
13]-10-pentadecene-3-one) as a .gamma.-butyrolactone structure; and
poly(4,15,16-trioxy-pentacyclo[10.2.1.0.sup.1,8.0.sup.2,7.0.sup.9,14]-11--
hexadecene-3-one) as a .delta.-valerolactone structure. Examples of
the cyclic acid anhydride structure include
poly(4,14,15-trioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3-one). Examples of the cyclic amide structure which can
form a lactam ring include
poly(4-methyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.su-
p.8,13]-10-pentadecene-3-one),
poly(4-ethyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup-
.8,13]-10-pentadecene-3-one),
poly(4-(n-propyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.-
0.sup.8,13]-10-pentadecene-3-one),
poly(4-(n-butyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0-
.sup.8,13]-10-pentadecene-3-one),
poly(4-(1-methylbutyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup-
.2,6.0.sup.8,13]-10-pentadecene-3-one),
poly(4-cyclopentyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6-
.0.sup.8,13]-10-pentadecene-3-one),
poly(4-cyclohexyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.-
0.sup.8,13]-10-pentadecene-3-one),
poly(4-phenyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.su-
p.8,13]-10-pentadecene-3-one), and
poly(4-(4-hydroxyphenyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.
0.sup.2,6.0.sup.8,13]-10-pentadecene-3-one) as .gamma.-lactam; and
poly(4-methyl-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.s-
up.9,14]-11-hexadecene-3-one),
poly(4-methyl-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.s-
up.9,14]-11-hexadecene-3-one),
poly(4-(n-propyl)-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7-
.0.sup.9,14]-11-hexadecene-3-one),
poly(4-(n-butyl)-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.-
0.sup.9,14]-11-hexadecene-3-one),
poly(4-(1-methylbutyl)-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.su-
p.2,7.0.sup.9,14]-11-hexadecene-3-one),
poly(4-cyclopentyl-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,-
7.0.sup.9,14]-11-hexadecene-3-one),
poly(4-cyclohexyl-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7-
.0.sup.9,14]-11-hexadecene-3-one),
poly(4-phenyl-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.sup.2,7.0.s-
up.9,14]-11-hexadecene-3-one), and
poly(4-(4-hydroxyphenyl)-4-aza-15,16-dioxy-pentacyclo[10.2.1.1.sup.1,8.0.-
sup.2,7.0.sup.9,14]-11-hexadecene-3-one) as .delta.-lactam.
Examples of the cyclic imide structure which can form a maleimide
ring include
poly(4-methyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.su-
p.8,13]-10-pentadecene-3,5-dione),
poly(4-ethyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup-
.8,13]-10-pentadecene-3,5-dione),
poly(4-(n-propyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.-
0.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-(n-butyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0-
.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-(1-methylbutyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup-
.2,6.0.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-cyclopentyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,-
6.0.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-cyclohexyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.-
0.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-phenyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.su-
p.8,13]-10-pentadecene-3,5-dione), and
poly(4-(4-hydroxyphenyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.
0.sup.2,6.0.sup.8,13]-10-pentadecene-3,5-dione).
[0103] Among these, in the repeating structural unit [B]
represented by Formula (2) according to the present embodiment, as
the cyclic olefin polymer in which n represents 1,
poly(8-methoxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-ethoxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene),
poly(8-(n-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7-
,10]-3-dodecene),
poly(8-(n-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,-
10]-3-dodecene),
poly(8-isobutoxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(tert-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-methyl-2-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-methyl-3-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(n-hexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.-
7,10]-3-dodecene),
poly(8-cyclohexyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-methyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(2,3-dimethyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2,3,3-trimethyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-hexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3,4-dimethyl-3-hexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-methylbutoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(2-methylpentoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3-methylpentoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(4-methylpentoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3-methyl-3-heptyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl)-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclopentylethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclooctyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclooctyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-methoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-ethoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(n-propoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(i-propoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-methyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-methyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-methoxycarbonylnaphthyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.s-
up.7,10]-3-dodecene),
poly(8-ethoxycarbonylnaphthyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.su-
p.7,10]-3-dodecene),
poly(8-(n-propoxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(i-propoxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.-
1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-11,12-dioxy-tetracycl-
o[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-11,12-dioxy-tetracycl-
o[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-phenoxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-benzyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(4-methylphenoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(3,4-dimethylphenoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-naphthoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-naphthoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(1-anthracenoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(methoxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1-
.sup.7,10]-3-dodecene),
poly(8-(ethoxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(n-propoxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-isopropoxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-butoxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclohexyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclooctyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-norbornyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylnorbornyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylnorbornyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxypropyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxy-1-methylethyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydrofuran-2-yloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydropyran-2-yloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-adamantyloxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-adamantyloxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-n-propoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-isopropoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-n-butoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-tert-butoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclooctyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-norboryloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydropyran-2-yloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-adamantyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-adamantyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(n-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetr-
acyclo[4.4.0.1
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tet-
racyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetr-
acyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclopentyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclohexyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-cyclooctyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-norbornyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylnorbornyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylnorbornyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxypropyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetracycl-
o[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethoxy-1-methylethyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydrofuran-2-yloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-tetrahydropyran-2-yloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-1-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-(1-adamantyl)-2-propoxycarbonyl)-ethoxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-(1-adamantyl)-2-propoxycarbonyl)-propoxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-11,12-di-
oxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tet-
racyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetr-
acyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy--
tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)-1-cyclopentyloxycarbonyl)-11,12-
-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-11,12-d-
ioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(6-tert-butoxycarbonyl-decahydronaphthalene-2-yloxycarbonyl)-1-
1,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(9-tert-butoxycarbonyl-11,12-dioxy-tetracyclo[6.2.1.1.sup.3,6.0.su-
p.2,7]-dodecane-4-yloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene), or
poly(8-(9-(1-methylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo[6.2.1.1.-
sup.3,6.0.sup.2,7]-dodecane-4-yloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene) is preferable.
[0104] Among these, from the viewpoints of improving the solubility
in a solvent (PGMEA) during preparation of a coating solution and
greatly changing the polarity of the cyclic olefin polymer after
application, in the repeating structural unit [B] represented by
Formula (2) according to the present embodiment, as the cyclic
olefin polymer in which n represents 1,
poly(8-(tert-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup-
.7,10]-3-dodecene),
poly(8-(2-methyl-2-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-methyl-3-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-3-methyl-3-pentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(2,3-dimethyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2,3,3-trimethyl-2-butoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-hexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(3,4-dimethyl-3-hexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-methyl-3-heptyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl)-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclopentylethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclooctyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclooctyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.-
sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methyldecahydronaphthalene-1-yloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethyldecahydronaphthalene-1-yloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyldecahydronaphthalene-2-yloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyldecahydronaphthalene-2-yloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2,7,7-trimethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-7,7-dimethyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-methyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-ethyl-octahydro-4,7-methano-indene-5-yloxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-methyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxyca-
rbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene)
poly(8-(3-(2-methyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-ethylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-methyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2,3-dimethyl-2-butoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclopentyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(2-cyclohexyl-2-propoxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclopentyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-methylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-(1-ethylcyclohexyloxycarbonyl)phenyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylphenyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5-
.1.sup.7,10]-3-dodecene),
poly(8-(n-pentyloxycarbonylnaphthyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-methyl-2-butoxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2,3-dimethyl-2-butoxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclopentyl-2-propoxycarbonyl)naphthyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(2-cyclohexyl-2-propoxycarbonyl)naphthyl)-11,12-dioxy-tetracycl-
o[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclopentyloxycarbonyl)naphthyl)-11,12-dioxy-tetracycl-
o[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclopentyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-ethylcyclohexyloxycarbonyl)naphthyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxymethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxymethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2-
,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,-
5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-n-propoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup-
.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-isopropoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.su-
p.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-n-butoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.-
2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-tert-butoxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.-
1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-cyclooctyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1-
.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-norboryloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.s-
up.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[-
4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclopentyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4-
.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylcyclohexyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylnorbornyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.-
4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethylnorbornyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4-
.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxypropyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-ethoxy-1-methylethyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyc-
lo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydrofuran-2-yloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(tetrahydropyran-2-yloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo-
[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-adamantyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-adamantyloxy)ethoxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.-
sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(tert-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetracyclo[4.4.0-
.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetr-
acyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclopentyl-2-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-cyclohexyl-2-propoxycarbonyl)propoxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-cyclohexyl-2-butoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-cyclohexyl-3-pentyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tet-
racyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-norbornyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-norbornyl-2-propoxycarbonylmethyloxycarbonyl-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(4-ethyl-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycar-
bonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-
-3-dodecene),
poly(8-(2-tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yl)-2-propoxyc-
arbonylmethyloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,1-
0]-3-dodecene),
poly(8-(1,1-dicyclohexylethoxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetr-
acyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1,1-dicyclohexylpropoxycarbonylmethyloxycarbonyl)-tetracyclo[4.4.-
0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclopentyloxycarbonylmethyloxycarbonyl-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclopentyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-methylcyclohexyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-ethylcyclohexyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetrac-
yclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-(1-adamantyl)-2-propoxycarbonyl)-ethoxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-(1-adamantyl)-2-propoxycarbonyl)-propoxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-(1-adamantyl)-2-propoxycarbonyl)-2-propoxycarbonyl)-11,12-di-
oxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-methyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tet-
racyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(2-methyl-2-adamantyloxycarbonyl)propoxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(2-methyl-2-adamantyloxycarbonyl)-2-propoxycarbonyl)-11,12-diox-
y-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(2-methyl-2-adamantyloxycarbonyl)ethoxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-ethyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-tetr-
acyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-isopropyl-2-adamantyloxycarbonylmethyloxycarbonyl)-11,12-dioxy--
tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-propoxycarbonylmethyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(2-(1-adamantyl)-2-butoxycarbonylmethyloxycarbonyl)-11,12-dioxy-te-
tracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-adamantyl)-3-pentyloxycarbonylmethyloxycarbonyl)-11,12-dioxy-
-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-tert-butoxycarbonyl-1-cyclopentyloxycarbonyl)-11,12-dioxy-tetra-
cyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(3-(1-methylcyclohexyloxycarbonyl)-1-cyclopentyloxycarbonyl)-11,12-
-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-tert-butoxycarbonyl-2-norbornyloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5-(1-methylcyclohexyloxycarbonyl)-2-norbornyloxycarbonyl)-11,12-d-
ioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,5-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(5,6-di(tert-butoxycarbonyl)-2-norbornyloxycarbonyl)-11,12-dioxy-t-
etracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(1-(1-methylcyclohexyloxycarbonyl)-octahydro-4,7-methano-indene-5--
yloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodece-
ne),
poly(8-(6-tert-butoxycarbonyl-decahydronaphthalene-2-yloxycarbonyl)-1-
1,12-dioxy-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene),
poly(8-(9-tert-butoxycarbonyl-11,12-dioxy-tetracyclo[6.2.1.1.sup.3,6.0.su-
p.2,7]-dodecane-4-yloxycarbonyl)-11,12-dioxy-tetracyclo[4.4.0.1
.sup.2,5.1.sup.7,10]-3-dodecene), or
poly(8-(9-(1-methylcyclohexyloxycarbonyl)-11,12-dioxy-tetracyclo
[6.2.1.1.sup.3,6.0.sup.2,7]-dodecane-4-yloxycarbonyl)-11,12-dioxy-tetracy-
clo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene) is more preferable.
[0105] Further, in the repeating structural unit [B] represented by
Formula (2) according to the present embodiment, in a case where
R.sup.5 to R.sup.8 are bonded to one another to form a ring
structure, as the cyclic olefin polymer in which n represents 1,
poly(4,14,15-trioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3-one),
poly(4,14,15-trioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup.8,13]-10-p-
entadecene-3,5-dione),
poly(4-methyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.su-
p.8,13]-10-pentadecene-3,5-dione),
poly(4-ethyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.sup-
.8,13]-10-pentadecene-3,5-dione),
poly(4-(n-propyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.-
0.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-(n-butyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0-
.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-(1-methylbutyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup-
.2,6.0.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-cyclopentyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,-
6.0.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-cyclohexyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.-
0.sup.8,13]-10-pentadecene-3,5-dione),
poly(4-phenyl-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.0.sup.2,6.0.su-
p.8,13]-10-pentadecene-3,5-dione), or
poly(4-(4-hydroxyphenyl)-4-aza-14,15-dioxy-pentacyclo[9.2.1.1.sup.1,7.
0.sup.2,6.0.sup.8,13]-10-pentadecene-3,5-dione) is preferable.
[0106] The cyclic olefin polymer according to the present
embodiment can be obtained by polymerizing, for example, a cyclic
olefin monomer represented by Formula (3) shown below and a cyclic
olefin monomer represented by formula (4) shown below through ring
opening metathesis polymerization.
##STR00008##
[0107] In Formula (3), R.sup.1 to R.sup.4 and n each have the same
definition as that in Formula (1).
[0108] The cyclic olefin monomer according to the present
embodiment may have two or more structural units in which at least
one of R.sup.1 to R.sup.4 in the structural unit represented by
Formula (3) is different from the rest.
##STR00009##
[0109] In Formula (4), R.sup.5 to R.sup.8, X.sub.1, and n each have
the same definition as that in Formula (2).
[0110] The cyclic olefin monomer according to the present
embodiment may have two or more structural units in which at least
one of R.sup.5 to R.sup.8 in the structural unit represented by
Formula (4) is different from the rest.
[0111] The catalyst used at the time of polymerizing the cyclic
olefin polymer according to the present embodiment is not
particularly limited as long as the catalyst is capable of
performing ring opening metathesis polymerization on the cyclic
olefin monomer, and examples thereof include an organic transition
metal alkylidene complex catalyst such as molybdenum (Mo), tungsten
(W), or ruthenium (Ru); and a ring opening metathesis catalyst
obtained by combining an organic transition metal catalyst and a
Lewis acid serving as a co-catalyst. Further, it is preferable to
use an organic transition metal alkylidene complex catalyst such as
molybdenum (Mo), tungsten (W), or ruthenium (Ru).
[0112] In the present embodiment, particularly, a highly polar
cyclic olefin monomer containing a heteroatom can be copolymerized.
For example, a highly polar cyclic olefin monomer can be
efficiently copolymerized in a case where an organic transition
metal alkylidene complex such as molybdenum (Mo), tungsten (W), or
ruthenium (Ru) is used.
[0113] Examples of the ring opening metathesis polymerization
catalyst of the organic transition metal alkylidene catalyst
include a tungsten-based alkylidene catalyst such as
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHBu.sup.t)(OBu.sup.t).sub.2,
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHBu.sup.t)(OCMe.sub.2CF.sub.3).sub-
.2,
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHBu.sup.t)(OCMe(CF.sub.3).sub.2-
).sub.2,
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OBu.sup.t).s-
ub.2,
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OCMe.sub.2CF.su-
b.3).sub.2,
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OCMe(CF.sub.3).sub.2-
).sub.2,
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OC(CF.sub.3)-
.sub.3).sub.2, or
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OC(CF.sub.3).sub.3).sub.2
(in the formulae, Pr.sup.i represents an iso-propyl group, Bu.sup.t
represents a tert-butyl group, Me represents a methyl group, and Ph
represents a phenyl group); a tungsten-based alkylidene catalyst
such as
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCMePh)(OBu.sup.t).sub.2(PMe.sub.3),
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCMe.sub.2)(OBu.sup.t).sub.2(PMe.sub.3-
),
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCPh.sub.2)(OBu.sup.t).sub.2(PMe.sub-
.3),
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCMePh)(OCMe.sub.2(CF.sub.3)).sub.-
2(PMe.sub.3),
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCMe.sub.2)(OCMe.sub.2(CF.sub.3)).sub.-
2(PMe.sub.3),
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCPh.sub.2)(OCMe.sub.2(CF.sub.3)).sub.-
2(PMe.sub.3),
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCMe.sub.2)(OCMe(CF.sub.3).sub.2).sub.-
2(PMe.sub.3),
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCMe.sub.2)(OCMe(CF.sub.3).sub.2).sub.-
2(PMe.sub.3),
W(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCHCPh.sub.2)(OCMe(CF.sub.3).sub.2).sub.-
2(PMe.sub.3),
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCHCMePh)(OCMe.sub.2(CF.sub.3)).su-
b.2(PMe.sub.3),
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCHCMePh)(OCMe(CF.sub.3).sub.2).su-
b.2(PMe.sub.3), or
W(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCHCMePh)(OPh).sub.2(PMe.sub.3)
(in the formulae, Pr.sup.i represents an iso-propyl group, Bu.sup.t
represents a tert-butyl group, Me represents a methyl group, and Ph
represents a phenyl group); a molybdenum-based alkylidene catalyst
such as
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHBu.sup.t)(OBu.sup.t).sub.2,
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHBu.sup.t)(OCMe.sub.2CF.sub.3).su-
b.2,
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHBu.sup.t)(OCMe(CF.sub.3).sub-
.2).sub.2,
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHBu.sup.t)(OC(CF.sub.3)-
.sub.3).sub.2,
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OBu.sup.t).sub.2,
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OCMe.sub.2CF.sub.3)-
.sub.2,
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OCMe(CF.sub.-
3).sub.2).sub.2,
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OC(CF.sub.3).sub.3)-
.sub.2,
Mo(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OBu.sup.t).sub.2,
Mo(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OCMe.sub.2CF.sub.3).sub.2-
,
Mo(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OCMe(CF.sub.3).sub.2).su-
b.2, or
Mo(N-2,6-Me.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OC(CF.sub.3).sub.3-
).sub.2 (in the formulae, Pr.sup.i represents an iso-propyl group,
Bu.sup.t represents a tert-butyl group, Me represents a methyl
group, and Ph represents a phenyl group); and a ruthenium-based
alkylidene catalyst such as Ru(P(C.sub.6H.sub.11).sub.3).sub.2
(CHPh)Cl.sub.2 (in the formula, Ph represents a phenyl group). The
ring opening metathesis polymerization catalyst may be used alone
or in combination of two or more kinds thereof.
[0114] Examples of the polymerization catalyst metal component at
the time of polymerizing the cyclic olefin polymer according to the
present embodiment include transition metals such as molybdenum,
tungsten, rhenium, iridium, tantalum, ruthenium, vanadium,
titanium, palladium, and rhodium. Among these, molybdenum,
tungsten, ruthenium, or rhodium is preferable, and molybdenum or
tungsten is more preferable.
[0115] The molar ratio of the cyclic olefin monomer to the ring
opening metathesis polymerization catalyst of the organic
transition metal alkylidene catalyst in the polymerization reaction
is in a range of 10 equivalents to 50000 equivalents, preferably in
a range of 50 equivalents to 30000 equivalents, and more preferably
in a range of 100 equivalents to 20000 equivalents with respect to
1 mol of the ring opening metathesis polymerization catalyst.
[0116] The polymerization reaction may be carried out with or
without a solvent. Examples of the solvent include ethers such as
tetrahydrofuran, diethyl ether, dibutyl ether, dimethoxyethane, and
dioxane; an aromatic hydrocarbon such as benzene, toluene, xylene,
or ethylbenzene; an aliphatic hydrocarbon such as pentane, hexane,
or heptane; an aliphatic cyclic hydrocarbon such as cyclopentane,
cyclohexane, methyl cyclohexane, dimethyl cyclohexane, or decalin;
a halogenated hydrocarbon such as methylene dichloride,
dichloroethane, dichloroethylene, tetrachloroethane, chlorobenzene,
or trichlorobenzene; and an ester such as methyl acetate or ethyl
acetate. These solvents may be used alone or in combination of two
or more kinds thereof.
[0117] Further, the polymerization reaction may be carried out in
the coexistence of a chain transfer agent such as olefins or
dienes. Examples of the olefins used as a chain transfer agent
include .alpha.-olefin such as ethylene, propylene, butene,
pentene, hexene, or octene; and silicon-containing olefin such as
vinyl trimethylsilane, allyl trimethylsilane, allyl triethylsilane,
or allyl triisopropylsilane. Further, examples of the dienes
include non-conjugated diene such as 1,4-pentadiene, 1,5-hexadiene,
or 1,6-heptadiene. The chain transfer agent may be used alone or in
combination of two or more kinds thereof.
[0118] The amount of the chain transfer agent which is allowed to
coexist is preferably in a range of 0.001 equivalents to 1000
equivalents and more preferably in a range of 0.01 equivalents to
100 equivalents with respect to 1 mol of the cyclic olefin monomer.
The amount of the chain transfer agent is more preferably in a
range of 0.1 equivalents to 2000 equivalents and more preferably in
a range of 1 equivalent to 1000 equivalents with respect to 1 mol
of the ring opening metathesis polymerization catalyst. The size of
the molecular weight can be adjusted by optionally setting these
ratios.
[0119] The monomer concentration in the polymerization reaction is
not particularly limited since the monomer concentration varies
depending on the reactivity of the cyclic olefin monomer or the
solubility in a polymerization solvent, but the concentration of
the cyclic olefin monomer is, for example, in a range of 0.001
kg/kg to 3 kg/kg, preferably in a range of 0.01 kg/kg to 2 kg/kg,
and more preferably in a range of 0.02 kg/kg to 1 kg/kg with
respect to 1 kg of the solvent. The reaction temperature is not
particularly limited since the reaction temperature varies
depending on the kind or the amount of the cyclic olefin monomer
and the ring opening metathesis catalyst, but is preferably in a
range of -30.degree. C. to 150.degree. C., preferably in a range of
0.degree. C. to 120.degree. C., and still more preferably in a
range of 15.degree. C. to 100.degree. C. The reaction time is, for
example, in a range of 1 minute to 10 hours, preferably in a range
of 5 minutes to 8 hours, and more preferably in a range of 10
minutes to 6 hours.
[0120] After the polymerization reaction, a cyclic olefin polymer
solution can be obtained by stopping the reaction using aldehydes
such as butyl aldehyde; ketones such as acetone; or alcohols such
as methanol. At this time, from the viewpoint of further
suppressing generation of volatile components (outgas) by reducing
the amount of unpolymerized monomers in the obtained cyclic olefin
polymer, the rate of polymerization of the cyclic olefin monomer is
preferably 90% or greater, more preferably 95% or greater, and
still more preferably 100%.
[0121] Further, the method of obtaining a polymer from the solution
of the cyclic olefin polymer is not particularly limited, and
examples thereof include a method of discharging the reaction
solution to a poor solvent being stirred; a method of precipitating
a polymer using a steam stripping method of blowing steam into the
reaction solution; and a method of evaporating and removing a
solvent from the reaction solution through heating.
[0122] Further, the cyclic olefin polymer represented by Formulae
(1) and (2) according to the present embodiment may be in the form
in which a double bond in the main chain is hydrogenated (also
referred to as hydrogenation). In this manner, further excellent
heat melt fluidity can be exhibited by releasing restriction on the
movement of a polymer chain using a double bond in the main chain,
for example, lowering the glass transition temperature of the
polymer and adjusting the temperature of the intersection between a
storage modulus (G') curve and a loss modulus (G'') curve which are
measured using a rheometer described below. As the result, an
underlayer film in which defects such as voids are further
suppressed and which has excellent flatness and exhibits an
excellent embedding property can be formed.
[0123] The hydrogenation ratio during the hydrogenation reaction is
preferably in a range of 0.1% to 100% by mole, more preferably in a
range of 1.0% to 95% by mole, and still more preferably in a range
of 5% to 90% by mole.
[0124] The catalyst for hydrogenating a double bond moiety in the
main chain of the polymer obtained by the ring opening metathesis
polymerization may be a homogeneous metal complex catalyst or a
heterogeneous metal-supported catalyst as long as the catalyst is
capable of carrying out hydrogenation. Among these, a heterogeneous
metal-supported catalyst which can easily separate a catalyst is
suitable, and preferred examples thereof include activated
carbon-supported palladium, alumina-supported palladium, activated
carbon-supported rhodium, alumina-supported rhodium, activated
carbon-supported ruthenium, and alumina-supported ruthenium. These
catalysts may be used alone or in combination of two or more kinds
thereof.
[0125] The solvent used for hydrogenation is not particularly
limited as long as the polymer is dissolved therein and the solvent
itself is not hydrogenated, and examples thereof include ethers
such as tetrahydrofuran, diethyl ether, dibutyl ether,
dimethoxyethane, and dioxane; an aromatic hydrocarbon such as
benzene, toluene, xylene, or ethylbenzene; an aliphatic hydrocarbon
such as pentane, hexane, or heptane; an aliphatic cyclic
hydrocarbon such as cyclopentane, cyclohexane, methyl cyclohexane,
dimethyl cyclohexane, or decalin; a halogenated hydrocarbon such as
methylene dichloride, dichloroethane, dichloroethylene,
tetrachloroethane, chlorobenzene, or trichlorobenzene; and an ester
such as methyl acetate or ethyl acetate. These solvents may be used
alone or in combination of two or more kinds thereof. Further, it
is preferable that a step which is suitable for productivity can be
employed without carrying out a solvent substitution step by means
of using the same kind of solvent as the solvent selected based on
the polymerization reaction described above.
[0126] In the hydrogenation reaction of the olefin moiety in the
main chain described above, the hydrogen pressure is preferably in
a range of the normal pressure to 10 MPa, more preferably in a
range of 0.5 to 8 MPa, and particularly preferably in a range of 2
to 5 MPa. Further, the reaction temperature is preferably in a
range of 0.degree. C. to 200.degree. C., more preferably in a range
of room temperature to 150.degree. C., and particularly preferably
in a range of 50.degree. C. to 100.degree. C. The mode in which the
hydrogenation reaction is carried out is not particularly limited,
and examples of the method of carrying out the hydrogenation
reaction include a method of carrying out the reaction by
dispersing or dissolving a catalyst in a solvent; and a method of
carrying out the reaction by filling a column or the like with a
catalyst and circulating a polymer solution as a stationary
phase.
[0127] Further, the hydrogenation treatment of the olefin moiety in
the main chain is not particularly limited. Hydrogenation treatment
may be carried out to a polymer redissolved in a solvent, after the
polymer is isolated by adding a poor solvent to a polymerization
solution that contains the polymer before hydrogenation treatment.
Further, hydrogenation treatment may be carried out using the
above-described hydrogenation catalyst, without isolating the
polymer from the polymerization solution.
[0128] Particularly, the method of obtaining a polymer from a
polymer solution in a case of preferably using a heterogeneous
metal-supported catalyst such as activated carbon rhodium or
activated carbon ruthenium after the hydrogenation is not
particularly limited, and examples thereof include a method of
obtaining a polymer solution which does not contain a catalyst
using a method of filtration, centrifugation, or decantation and
discharging the reaction solution to a poor solvent being stirred;
a method of precipitating a polymer using a steam stripping method
of blowing steam into the reaction solution; and a method of
evaporating and removing a solvent from the reaction solution
through heating.
[0129] Further, in a case where the hydrogenation reaction is
carried out using a heterogeneous metal-supported catalyst, the
polymer can be obtained according to the above-described method
after a synthetic solution is filtered and the metal-supported
catalyst is separated by filtration. In order to obtain a polymer
solution particularly free of a metal which is used in a
semiconductor device manufacturing step, the polymer may be
obtained according to the above-described method after a solution
obtained by roughly removing a catalyst component is filtered.
Particularly, it is suitable to perform microfiltration on the
catalyst component, and the pore diameter of a filtration filter is
preferably in a range of 10 .mu.m to 0.05 .mu.m, particularly
preferably in a range of 10 .mu.m to 0.10 .mu.m, and still more
preferably in a range of 5 .mu.m to 0.10 .mu.m.
[0130] In the cyclic olefin polymer according to the present
embodiment, the weight-average molecular weight (Mw) thereof in
terms of polystyrene which is measured by gel permeation
chromatography (GPC) at a sample concentration of 3.0 to 9.0 mg/ml
is preferably in a range of 1000 to 20000, more preferably in a
range of 1500 to 19000, and still more preferably in a range of
2000 to 18000. In a case where the weight-average molecular weight
(Mw) is set to be in the above-described range, further excellent
heat melt fluidity can be exhibited at the time of heating the
surface of the uneven structure of the substrate at a temperature
of 200.degree. C. to 250.degree. C., which is applied in a typical
semiconductor device manufacturing step, the heating thereof is
performed in a baking step after the surface thereof is coated with
the material for forming an underlayer film according to the
present embodiment. As the result, an underlayer film in which
defects such as voids are further suppressed and which has
excellent flatness and exhibits an excellent embedding property can
be formed.
[0131] The molecular weight distribution (Mw/Mn), which is a ratio
between the weight-average molecular weight (Mw) and the number
average molecular weight (Mn) in a case where the molecular weight
(Mw) is in the above-described range, is preferably in a range of
1.3 to 5.0, more preferably in a range of 1.3 to 4.0, and still
more preferably in a range of 1.3 to 3.0. In a case where the
molecular weight distribution (Mw/Mn) is set to be in the
above-described range, the melt unevenness with respect to the
heating during the baking step can be further suppressed, and the
resin is further uniformly melted. As the result, an underlayer
film in which defects such as voids are further suppressed and
which has excellent flatness and exhibits an excellent embedding
property can be formed.
[0132] As a measure of showing the melt fluidity through the
heating described above, for example, the temperature showing an
intersection between a storage modulus (G') curve and a loss
modulus (G'') curve in measurement of the solid viscoelasticity of
the cyclic olefin polymer or the material for forming an underlayer
film according to the present embodiment can be used (see FIG.
1).
[0133] The intersection between the storage modulus (G') curve and
the loss modulus (G'') curve can be used as a measure of showing a
change of rheology of a substance (also referred to as a resin).
Typically, the substance in a temperature rising step up to the
intersection shows characteristics as an elastic body, and the
resin does not flow. Further, the substance shows characteristics
as a viscous fluid by being heated to a higher temperature through
the intersection, and thus the resin flows. In other words, in
order to embed the uneven surface of the substrate in a further
uniform state while suppressing defects such as voids, it is
preferable that moderate fluidity is exhibited. In other words, in
the cyclic olefin polymer or the material for forming an underlayer
film according to the present embodiment, in a case where the
intersection between the storage modulus (G') curve and the loss
modulus (G'') curve is preferably in a range of 40.degree. C. to
200.degree. C., more preferably in a range of 40.degree. C. to
195.degree. C., and still more preferably in a range of 40.degree.
C. to 190.degree. C., the cyclic olefin polymer or the material for
forming an underlayer film according to the present embodiment can
exhibit moderate fluidity required to uniformly embed the uneven
structure of the surface of the substrate under a heating condition
of 200.degree. C. to 250.degree. C. which has been typically used
in a semiconductor device manufacturing step.
[0134] The lower limit of the intersection between the storage
modulus (G') curve and the loss modulus (G'') curve is more
preferably 80.degree. C. or higher, still more preferably
90.degree. C. or higher, and particularly preferably 100.degree. C.
or higher. Further, the upper limit of the intersection between the
storage modulus (G') curve and the loss modulus (G'') curve is
preferably 200.degree. C. or lower, more preferably 195.degree. C.
or higher, and particularly preferably 190.degree. C. or lower.
[0135] Here, the solid viscoelasticity of the cyclic olefin polymer
or the material for forming an underlayer film according to the
present embodiment can be measured under conditions of a
measurement temperature range of 30.degree. C. to 300.degree. C.
(or in a range of 50.degree. C. to 250.degree. C.), a heating rate
of 3.degree. C./min, and a frequency of 1 Hz in a nitrogen
atmosphere in a shear mode using a rheometer.
[0136] In a case where the intersection between the storage modulus
(G') curve and the loss modulus (G'') curve is less than or equal
to the above-described upper limit, the cyclic olefin polymer or
the material for forming an underlayer film according to the
present embodiment shows the characteristics as a viscous fluid,
the resin flows, and the uneven surface of the substrate can be
embedded in a more uniform state while defects such as voids are
further suppressed.
[0137] Further, in a case where the intersection between the
storage modulus (G') curve and the loss modulus (G'') curve is
greater than or equal to the above-described lower limit, the
fluidity of the cyclic olefin polymer or the material for forming
an underlayer film according to the present embodiment can be
suppressed. As the result, shrinkage in the uneven surface of the
substrate can be further suppressed, and the uneven surface of the
substrate can be embedded in a more uniform state while defects
such as voids are further suppressed.
[0138] In addition, the amount of the volatile component in the
cyclic olefin polymer according to the present embodiment which is
measured using the following method 1 is preferably greater than or
equal to 0.0% by mass and less than or equal to 1.0% by mass, more
preferably greater than or equal to 0.0% by mass and less than or
equal to 0.7% by mass, still more preferably greater than or equal
to 0.0% by mass and less than or equal to 0.5% by mass, and
particularly preferably greater than or equal to 0.0% by mass and
less than or equal to 0.1% by mass.
[0139] In this manner, since generation of the volatile component
(outgas) accompanied by decomposition of the polymer at the time of
heating and melting can be suppressed, a resist underlayer film
with further excellent flatness can be formed.
[0140] In other words, a resist underlayer film which is capable of
suppressing intermixing of an intermediate layer provided as an
upper layer with the material used as a resist layer and
suppressing generation of voids or the like, and has an embedding
property in a further excellent state and further excellent
flatness can be formed.
[0141] The method 1: The cyclic olefin polymer according to the
present embodiment is dissolved in tetrahydrofuran to prepare a
solution having a solid content concentration (or a polymer
concentration) of 20% by mass, the obtained solution is weighed
using an aluminum plate, heated at 200.degree. C. for 3 minutes in
a nitrogen flow so that the tetrahydrofuran is removed, and cooled
to room temperature so that the cyclic olefin polymer is
solidified, the cyclic olefin polymer is heated in a temperature
range of 30.degree. C. to 300.degree. C. at a heating rate of
10.degree. C./min in a nitrogen atmosphere, and the amount of the
volatile component in the cyclic olefin polymer is calculated based
on a weight reduction amount in a temperature range of 100.degree.
C. to 250.degree. C.
[0142] Further, it is preferable that the cyclic olefin polymer or
the material for forming an underlayer film according to the
present embodiment can be dissolved in any organic solvent
(preferably propylene glycol-1-monomethylether-2-acetate (PGMEA))
used to prepare a varnish-like material for forming an underlayer
film at least at a concentration of greater than or equal to 0.01%
by mass and less than or equal to 50% by mass, and the residual
film rate of the cyclic olefin polymer or the material for forming
an underlayer film according to the present embodiment which is
measured using the following method 4 is preferably greater than or
equal to 50% and less than or equal to 100% and more preferably
greater than or equal to 60% and less than or equal to 100%.
[0143] Method 4: A coating film which is formed of the cyclic
olefin polymer or the material for forming an underlayer film
according to the present embodiment and has a thickness (.alpha.)
of greater than or equal to 200 nm and less than or equal to 500 nm
is formed on a silicon wafer. Next, the obtained coating film is
treated at 200.degree. C. for 10 minutes. Subsequently, the coating
film is immersed in at least one organic solvent selected from the
group consisting of an alcohol-based solvent, an ether-based
solvent, a ketone-based solvent, an amide-based solvent, an
ester-based solvent, and a hydrocarbon-based solvent (preferably
propylene glycol-1-monomethyl ether-2-acetate (PGMEA)) at
23.degree. C. for 10 minutes and dried under conditions of
150.degree. C. for 3 minutes so that a remaining solvent in the
coating film is removed. Next, a thickness (.beta.) of the coating
film obtained by removing the remaining solvent is measured, and
the residual film rate (=.beta./.alpha..times.100) (%) is
calculated.
[0144] Examples of the alcohol-based solvent include an aliphatic
monoalcohol-based solvent such as 4-methyl-2-pentanol or n-hexanol;
an alicyclic monoalcohol-based solvent having 3 to 18 carbon atoms
such as cyclohexanol; a polyhydric alcohol-based solvent having 2
to 18 carbon atoms such as 1,2-propylene glycol; and a polyhydric
alcohol partial ether-based solvent having 3 to 19 carbon atoms
such as propylene glycol monomethyl ether.
[0145] Examples of the ether-based solvent include a dialkyl
ether-based solvent such as diethyl ether, dipropyl ether, or
dibutyl ether; a cyclic ether-based solvent such as tetrahydrofuran
or tetrahydropyran; and an aromatic ring-containing ether-based
solvent such as diphenyl ether or anisole.
[0146] Examples of the ketone-based solvent include a chain-like
ketone-based solvent such as acetone, methyl ethyl ketone,
methyl-n-propyl ketone, methyl-n-butyl ketone, diethyl ketone,
methyl-iso-butyl ketone, 2-heptanone, ethyl-n-butyl ketone,
methyl-n-hexyl ketone, di-iso-butyl ketone, or trimethyl nonanone;
a cyclic ketone-based solvent such as cyclopentanone,
cyclohexanone, cycloheptanone, cyclooctanone, or methyl
cyclohexanone; and 2,4-pentanedione, acetonylacetone, or
acetophenone.
[0147] Examples of the amide-based solvent include a cyclic
amide-based solvent such as N,N'-dimethylimidazolidinone or
N-methylpyrrolidone; and a chain-like amide-based solvent such as
N-methylformamide, N,N-dimethylformamide, N,N-diethylformamide,
acetamide, N-methylacetamide, N,N-dimethylacetamide, or
N-methylpropionamide.
[0148] Examples of the ester-based solvent include a monocarboxylic
acid ester-based solvent such as n-butyl acetate or ethyl lactate;
a polyhydric alcohol carboxylate-based solvent such as propylene
glycol acetate; a polyhydric alcohol partial ether
carboxylate-based solvent such as polyhydric alcohol partial alkyl
ether acetate of propylene glycol-1-monomethyl ether-2-acetate or
the like; a polyhydric carboxylic acid diester-based solvent such
as diethyl oxalate; a lactone-based solvent such as
.gamma.-butyrolactone or .delta.-valerolactone; and a
carbonate-based solvent such as diethyl carbonate, ethylene
carbonate, or propylene carbonate.
[0149] Examples of the hydrocarbon-based solvent include a linear
or branched hydrocarbon having 5 to 10 carbon atoms, an alicyclic
hydrocarbon having 5 to 12 carbon atoms, and an aromatic
hydrocarbon having 6 to 18 carbon atoms. Some or all hydrogen atoms
on a ring of the alicyclic hydrocarbon and the aromatic hydrocarbon
may be substituted with a linear or branched alkyl group having 1
to 5 carbon atoms.
[0150] Among these, from the viewpoint of the adaptability to the
process or the like, at least one selected from the group
consisting of an alcohol-based solvent and an ester-based solvent
is preferable. Examples of the alcohol-based solvent include
propylene glycol monomethyl ether (PGME) and propylene glycol
monopropyl ether (PGPE) Examples of the ester-based solvent include
propylene glycol-1-monomethyl ether-2-acetate (PGMEA). These
solvents may be used alone or in the form of a mixture of two or
more kinds thereof.
[0151] In a case where the residual film rate of the cyclic olefin
polymer according to the present embodiment is greater than or
equal to the lower limit, intermixing can be suppressed during the
formation of an intermediate layer on the resist underlayer film.
As the result, a laminate which has excellent adhesiveness between
the intermediate layer and the resist underlayer film and excellent
flatness can be realized.
[0152] Here, the residual film rate may be in the above-described
range in a case where at least one organic solvent selected from
the group consisting of an alcohol-based solvent, an ether-based
solvent, a ketone-based solvent, an amide-based solvent, an
ester-based solvent, and a hydrocarbon-based solvent is used as an
organic solvent, and it is preferable that the residual film rate
is in the above-described range in a case where propylene
glycol-1-monomethyl ether-2-acetate (PGMEA) is used as an organic
solvent.
[0153] The glass transition temperature of the cyclic olefin
polymer according to the present embodiment based on the
differential scanning calorimetry is preferably in a range of
40.degree. C. to 220.degree. C., more preferably in a range of
40.degree. C. to 200.degree. C., and still more preferably in a
range of 40.degree. C. to 180.degree. C. Further, the glass
transition temperature of the cyclic olefin polymer according to
the present embodiment based on the differential scanning
calorimetry is preferably 40.degree. C. or higher, more preferably
50.degree. C. or higher, still more preferably 60.degree. C. or
higher, and even still more preferably 70.degree. C. or higher and
preferably 220.degree. C. or lower, more preferably 200.degree. C.
or lower, and still more preferably 180.degree. C. or lower. In a
case where the glass transition temperature thereof is in the
above-described range, the temperature of the intersection between
the storage modulus (G') curve and the loss modulus (G'') curve is
easily adjusted to be in the above-described range.
[0154] Further, for example, a method of performing SEM observation
on a sample obtained by embedding the uneven surface of the
substrate through formation of a coating film according to a spin
coating method and cutting out the cross section of the sample
after being baked is used for evaluation of the flatness of the
resist underlayer film. In this case, it is preferable that the
following flatness (.DELTA.FT) can be used as a measure of showing
the degree of fluctuation of the atmospheric surface. First, ten
heights from the bottoms of recesses to the atmospheric surface (a
surface (.alpha.) described below) in the uneven structure of the
substrate are measured, and the average value (H.sub.av) is set as
the film thickness. Next, based on the result obtained by measuring
the maximum value (H.sub.max) and the minimum value (H.sub.min)
among the film thicknesses in fluctuation, a value
([(H.sub.max-H.sub.min)/H.sub.av].times.100(%)) obtained by
dividing a difference (H.sub.max-H.sub.min) between the maximum
value and the minimum value by the average value of the film
thicknesses is set as the measure of the flatness (.DELTA.FT).
Here, in a case where the substrate does not have an uneven
structure, the "heights from the bottoms of recesses to the
atmospheric surface" may be replaced by the "height from the
surface of the substrate to the atmospheric surface".
[0155] FIG. 2 are schematic views for describing a film thickness 4
of a resist underlayer film 2, a height 5 of an uneven structure 7,
and an interval 6 between projections of the uneven structure 7 in
a laminate 10 according to the embodiment of the present invention.
As shown in FIG. 2, in a case where a substrate 1 has the uneven
structure 7, the height from the bottom of a recess to a surface
(.alpha.) 3 is set as a film thickness 4 of the resist underlayer
film 2. Further, in a case where the substrate 1 does not have the
uneven structure 7, the height from the surface of the substrate 1
to the surface (.alpha.) 3 is set as the film thickness 4 of the
resist underlayer film 2.
[0156] The flatness (.DELTA.FT) is preferably in a range of 0% to
5%, more preferably in a range of 0% to 3%, and still more
preferably in a range of 0% to 1%. In this manner, the thickness of
the resist layer can be made more uniform regardless of the
presence of the intermediate layer, and a desired pattern in
lithography can be obtained with excellent reproducibility.
[0157] Further, for example, a method of performing SEM observation
on a sample obtained by embedding the uneven surface of the
substrate through formation of a coating film according to a spin
coating method and cutting out the cross section of the sample
after being baked is used for evaluation of the difference in film
thickness in an isolated or dense pattern of the resist underlayer
film. In this case, in a switching portion of the isolated and
dense pattern, as shown in FIG. 3-2, in a case where the width
between projections (recess width) in the uneven structure of the
substrate is set as a and the projection width is set as b, the
ratio [a/(a+b)] of the width between projections to the pattern
pitch width represented by a+b is set as .alpha., and the .alpha.
value, .alpha..sub.1, and .alpha..sub.2 for each of the pattern
areas with different widths between projections and different
projection widths on the same substrate are acquired. The switching
portion of the isolated and dense pattern is obtained in a case
where the absolute value of the difference between .alpha.1 and
.alpha.2 is in a range of 0<|.alpha.1-.alpha.2|<1. In the
difference in film thickness in the switching portion of the
isolated and dense pattern, ten film thicknesses from the bottoms
of recesses to the atmospheric surface in each of the pattern
regions on the same substrate with different .alpha. values are
measured, an average value H.sub.1, an average value H.sub.2, and
an average value H.sub.3 of H.sub.1 and H.sub.2 are respectively
acquired, and a value (|H.sub.1-H.sub.2|/H.sub.3.times.100(%))
obtained by dividing the absolute value |H.sub.1-H.sub.2| of the
difference between the average film thicknesses from the bottoms of
recesses to the atmospheric surface in two pattern regions by
H.sub.3 is set as the measure of the flatness (.DELTA.FT).
[0158] In FIG. 3-2, "a.sub.1/(a.sub.1+b.sub.1)=.alpha..sub.1" and
"a.sub.2/(a.sub.2+b.sub.2)=.alpha..sub.2" are satisfied. H.sub.1
and H.sub.2 each indicate the average film thickness from the
bottoms of recesses to the atmospheric surface in the regions of
.alpha..sub.1 and .alpha..sub.2, and
"|H.sub.1-H.sub.2|/H.sub.3.times.100(%)=.DELTA.FT" is
satisfied.
[0159] The flatness (.DELTA.FT) is preferably in a range of 0% to
5%, more preferably in a range of 0% to 3%, and still more
preferably in a range of 0% to 1%. In this manner, the thickness of
the resist layer can be made more uniform regardless of the
presence of the intermediate layer, and a desired pattern in
lithography can be obtained with excellent reproducibility.
[0160] In an ArF photolithography step of transferring a pattern of
a photomask using an ArF excimer laser having a wavelength of 193
nm to a layer formed of a resist material formed over the
underlayer film, light having passed through the underlayer film
from the resist layer is reflected on the surface of the
semiconductor substrate and is incident on the resist layer on the
upper side from the underlayer film again. In other words, the
roughness of the pattern may deteriorate because optical
interference occurs due to the influence of a stationary wave and
this result in non-uniform concentration of an acid generated
inside the resist. Further, in a case where a substrate having a
plurality of trenches particularly with aspect ratios different
from one another, reflection of light causes irregular reflection
on a stepped portion, and the irregular-reflected light is incident
on the resist layer from the underlayer film again. Therefore, a
phenomenon in which the transfer accuracy deteriorates due to the
acid generated by the light which has been incident inside the
resist layer that should be an unexposed portion occurs.
[0161] In order to prevent deterioration of pattern roughness or
deterioration of transfer accuracy due to a stationary wave or
irregular reflection on the resist layer from the underlayer film,
the underlayer film is required to have a function as an
anti-reflection film. Practically, it is considered that the
reflectivity into the resist film from the underlayer film needs to
be suppressed to less than or equal to 1%.
[0162] As a specific method of allowing the underlayer film to
exhibit the function as an anti-reflection film, a method of
controlling an optical constant of the material for forming an
underlayer film has been known.
[0163] The reflectivity to the resist film from the underlayer film
can be set to less than or equal to 1% by controlling a refractive
index (n value) of the cyclic olefin polymer or the material for
forming an underlayer film according to the present embodiment at a
wavelength of 193 nm which is measured using the following method 2
and an extinction coefficient (k value) of the cyclic olefin
polymer or the material for forming an underlayer film according to
the present embodiment which is measured using the following method
3 such that the n value and the k value are preferably set to be in
a range of 1.5 to 2.0 and 0.0001 to 0.5 respectively, more
preferably set to be in a range of 1.55 to 1.95 and 0.0001 to 0.4
respectively, and still more preferably set to be in a range of 1.6
to 1.9 and 0.0001 to 0.3 respectively. Further, from the viewpoint
of exhibiting the anti-reflection performance, it is preferable
that the anti-reflection film has a flat shape. From the viewpoint
of forming an anti-reflection film it is preferable that the
present embodiment is employed since the surface of the base film
can be made flat.
[0164] Method 2: A coating film which is formed of the cyclic
olefin polymer or the material for forming an underlayer film and
has a thickness of 250 nm is formed on a silicon wafer, and the
refractive index (n value) of the obtained coating film at a
wavelength of 193 nm is set as the refractive index (n value) of
the material for forming an underlayer film.
[0165] Method 3: A coating film which is formed of the cyclic
olefin polymer or the material for forming an underlayer film and
has a thickness of 250 nm is formed on a silicon wafer, and the
extinction coefficient (k value) of the obtained coating film is
set as the extinction coefficient (k value) of the cyclic olefin
polymer or the material for forming an underlayer film.
[0166] Further, the average value Hay (the film thicknesses of the
resist underlayer film at ten optional sites of the surface
(.alpha.) of the resist underlayer film on a side opposite to the
substrate are measured, and the average value of these is set as
Hay) of the film thicknesses (the distances from the upper portion
of the substrate to the surface of the underlayer film at several
optional sites are measured in a case where the substrate that does
not have an uneven structure is used, and the distances from the
bottoms of recesses of the substrate to the surface of the
underlayer film are measured in a case where a substrate having an
uneven structure is used) of the underlayer film used here is
preferably in a range of 5 to 1000 nm, more preferably in a range
of 5 to 800 nm, still more preferably in a range of 5 to 600 nm,
even still more preferably in a range of 5 to 500 nm, even still
more preferably in a range of 7 to 450 nm, and even still more
preferably in a range of 10 to 400 nm. Further, the lower limit of
the average value H.sub.av of the film thicknesses of the resist
underlayer film is preferably 5 nm or greater, more preferably 7 nm
or greater, and still more preferably 10 nm or greater, and the
upper limit thereof is preferably 1000 nm or less, more preferably
800 nm or less, still more preferably 600 nm or less, even still
more preferably 500 nm or less, even still more preferably 450 nm
or less, and even still more preferably 400 nm or less. In a case
where the n value and the k value are respectively in the
above-described range and the thickness of the underlayer film is
in the above-described range, a processed substrate which is free
of roughness in the pattern of the photomask and is transferred
with high accuracy in the ArF photolithography step can be
obtained.
[0167] <Preparation of Varnish-Like Material for Forming
Underlayer Film>
[0168] The material for forming an underlayer film according to the
present embodiment can be made into a varnish-like material for
forming an underlayer film which is suitable for being applied to
the substrate by dissolving or dispersing the cyclic olefin polymer
according to the present embodiment in an organic solvent and
removing foreign matter through a filter having pores according to
the size of a desired pattern as necessary.
[0169] The organic solvent used here is not particularly limited as
long as the cyclic olefin polymer according to the present
embodiment can be dissolved or dispersed in the solvent.
[0170] Examples of the organic solvent include an alcohol-based
solvent, an ether-based solvent, a ketone-based solvent, an
amide-based solvent, an ester-based solvent, and a
hydrocarbon-based solvent.
[0171] Examples of the alcohol-based solvent include an aliphatic
monoalcohol-based solvent such as 4-methyl-2-pentanol or n-hexanol;
an alicyclic monoalcohol-based solvent having 1 to 18 carbon atoms
such as cyclohexanol; a polyhydric alcohol-based solvent having 2
to 18 carbon atoms such as 1,2-propylene glycol; and a polyhydric
alcohol partial ether-based solvent having 3 to 19 carbon atoms
such as propylene glycol monomethyl ether.
[0172] Examples of the ether-based solvent include a dialkyl
ether-based solvent such as diethyl ether, dipropyl ether, or
dibutyl ether; a cyclic ether-based solvent such as tetrahydrofuran
or tetrahydropyran; and an aromatic ring-containing ether-based
solvent such as diphenyl ether or anisole.
[0173] Examples of the ketone-based solvent include a chain-like
ketone-based solvent such as acetone, methyl ethyl ketone,
methyl-n-propyl ketone, methyl-n-butyl ketone, diethyl ketone,
methyl-iso-butyl ketone, 2-heptanone, ethyl-n-butyl ketone,
methyl-n-hexyl ketone, di-iso-butyl ketone, or trimethyl nonanone;
a cyclic ketone-based solvent such as cyclopentanone,
cyclohexanone, cycloheptanone, cyclooctanone, or methyl
cyclohexanone; and 2,4-pentanedione, acetonylacetone, or
acetophenone.
[0174] Examples of the amide-based solvent include a cyclic
amide-based solvent such as N,N'-dimethylimidazolidinone or
N-methylpyrrolidone; and a chain-like amide-based solvent such as
N-methylformamide, N,N-dimethylformamide, N,N-diethylformamide,
acetamide, N-methylacetamide, N,N-dimethylacetamide, or
N-methylpropionamide.
[0175] Examples of the ester-based solvent include a monocarboxylic
acid ester-based solvent such as n-butyl acetate or ethyl lactate;
a polyhydric alcohol carboxylate-based solvent such as propylene
glycol acetate; a polyhydric alcohol partial ether
carboxylate-based solvent such as polyhydric alcohol partial alkyl
ether acetate of propylene glycol-monomethyl ether-acetate or the
like; a polyhydric carboxylic acid diester-based solvent such as
diethyl oxalate; a lactone-based solvent such as
.gamma.-butyrolactone or .delta.-valerolactone; and a
carbonate-based solvent such as diethyl carbonate, ethylene
carbonate, or propylene carbonate.
[0176] Examples of the hydrocarbon-based solvent include a linear
or branched hydrocarbon having 5 to 10 carbon atoms, an alicyclic
hydrocarbon having 5 to 12 carbon atoms, and an aromatic
hydrocarbon having 6 to 18 carbon atoms. Some or all hydrogen atoms
on a ring of the alicyclic hydrocarbon and the aromatic hydrocarbon
may be substituted with a linear or branched alkyl group having 1
to 5 carbon atoms.
[0177] Among these, the solvent is selected in consideration of the
volatilization rate of the solvent at the time of application, the
adaptability to the process, and the productivity, and it is
preferable that an oxygen-containing solvent such as an
alcohol-based solvent, a chain-like ketone-based solvent, a cyclic
ether-based solvent, or an ester-based solvent is selected. The
material for forming an underlayer film according to the present
embodiment may contain one or two or more kinds of solvents.
[0178] Further, the concentration of the cyclic olefin polymer in
the varnish-like material for forming an underlayer film according
to the present embodiment is preferably in a range of 0.01% to
50.0% by mass, more preferably in a range of 0.1% to 45.0% by mass,
and still more preferably in a range of 1.0% to 40.0% by mass. The
concentration of the cyclic olefin polymer can be selected in
consideration of the solubility of the polymer, the adaptability to
the filtration process, the film forming property, the thickness of
the underlayer film, and the like.
[0179] Further, for the purpose of adjusting the physical
properties of the material as the underlayer film such as the
etching resistance and optical characteristics, a resin such as an
acrylic resin, an epoxy resin, a styrene resin, a hydroxystyrene
resin, a hydroxynaphthylene resin, or a silicone resin; a monomer
constituting the resin in a case of a combination of the resin and
a polymerization initiator; a thermosetting monomer; a polymer
material; and an oxide of a metal such as zirconium, hafnium,
ruthenium, or titanium may be mixed into the material for forming
an underlayer film according to the present embodiment within the
range where the effects of the present invention are not
impaired.
[0180] Further, in a case of providing the resist layer and the
resist underlayer film or an intermediate layer between the resist
layer and the resist underlayer film, the material for forming an
underlayer film according to the present embodiment may contain a
crosslinking agent within the range where the effects of the
present invention are not impaired, for the purpose of suppressing
intermixing of the intermediate layer with the resist underlayer
film. Meanwhile, in a case where a crosslinking agent is used, the
influence of reaction shrinkage at the time of curing may become
significant. For example, in a case where the pattern of unevenness
is irregular, the amount of the crosslinking agent is extremely
large, and the distance between projections is long, the influence
of the shrinkage cannot be ignored in some cases. Accordingly, the
flatness may be degraded. Therefore, it is preferable that the
content of the crosslinking agent in the material for forming an
underlayer film according to the present embodiment is small. From
this viewpoint, in a case where the total content of the polymer
component contained in the material for forming an underlayer film
is set as 100 parts by mass, the content of the crosslinking agent
is preferably less than 5 parts by mass, more preferably less than
3 parts by mass, and still more preferably less than 1 part by
mass.
[0181] A polyfunctional epoxy compound, an oxetane compound, or the
like is suitably used as the crosslinking agent, but the
crosslinking agent is not particularly limited to these
compounds.
[0182] Examples of the polyfunctional epoxy compound include epoxy
compounds, for example, alicyclic epoxy resins or glycidyl ether of
hydrogenated bisphenol A, such as 1,7-octadiene diepoxide, limonene
dioxide, 4-vinyl cyclohexene dioxide,
3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate,
di(3,4-epoxycyclohexyl)adipate,
(3,4-epoxy-6-methylcyclohexyl)methyl-3,4-epoxy-6-methylcyclohexane
carboxylate, ethylene 1,2-di(3,4-epoxycyclohexanecarboxylic acid)
ester, 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexane
carboxylate, bis(3,4-epoxycyclohexylmethyl) adipate, a bisphenol A
type epoxy resin, a halogenated bisphenol A type epoxy resin, a
bisphenol F type epoxy resin, an o-, m-, or p-cresol novolak type
epoxy resin, a phenol novolak type epoxy resin, polyglycidyl ether
of polyhydric alcohol, and
3,4-epoxycyclohexenylmethyl-3',4'-epoxycyclohexene carboxylate.
[0183] Examples of the polyfunctional oxetane compound include
bis(3-ethyl-3-oxetanylmethyl)ether,
1,2-bis[(3-ethyl-3-oxetanylmethoxy)]ethane,
1,3-bis[(3-ethyl-3-oxetanylmethoxy)]propane,
1,3-bis[(3-ethyl-3-oxetanylmethoxy)]-2,2-dimethyl-propane,
1,4-bis(3-ethyl-3-oxetanylmethoxy)butane,
1,6-bis(3-ethyl-3-oxetanylmethoxy)hexane,
1,4-bis[(3-methyl-3-oxetanyl)methoxy]benzene,
1,3-bis[(3-methyl-3-oxetanyl)methoxy]benzene,
1,4-bis{[(3-methyl-3-oxetanyl)methoxy]methyl}cyclohexane,
4,4'-bis{[3-methyl-3-oxetanyl]methoxy}methyl}biphenyl,
4,4'-bis{[(3-methyl-3-oxetanyl)methoxy]methyl}bicyclohexane,
2,3-bis[(3-methyl-3-oxetanyl)methoxy]bicyclo[2.2.1]heptane,
2,5-bis[(3-methyl-3-oxetanyl)methoxy]bicyclo[2.2.1]heptane,
2,6-bis[(3-methyl-3-oxetanyl)methoxy]bicyclo[2.2.1]heptane,
1,4-bis[(3-ethyl-3-oxetanyl)methoxy]benzene,
1,3-bis[(3-ethyl-3-oxetanyl)methoxy]benzene,
1,4-bis{[3-ethyl-3-oxetanyl]methoxy}methyl}benzene,
1,4-bis-{[(3-ethyl-3-oxetanyl)methoxy]methyl}cyclohexane,
4,4'-bis{[(3-ethyl-3-oxetanyl)methoxy]methyl}biphenyl,
4,4'-bis{[(3-ethyl-3-oxetanyl)methoxy]methyl}bicyclohexane,
2,3-bis[(3-ethyl-3-oxetanyl)methoxy]bicyclo[2.2.1]heptane,
.sup.2,5-bis[(3-ethyl-3-oxetanyl) methoxy]bicyclo[2.2.1]heptane,
and 2,6-bis[(3-ethyl-3-oxetanyl)methoxy]bicyclo[2.2.1]heptane.
Further, these crosslinking agents may be used alone or in
combination of two or more kinds thereof.
[0184] Next, the varnish-like material for forming an underlayer
film which has been prepared using the above-described method is
filtered by being allowed to pass through a filter. In this manner,
polymer insoluble, gels, or foreign matter can be removed from the
varnish-like material for forming an underlayer film, and a uniform
layer as an underlayer film can be formed between the resist film
layer and the surface of the substrate.
[0185] The pore diameter of the filtration filter is preferably in
a range of 1 .mu.m to 0.001 .mu.m, more preferably in a range of
0.5 .mu.m to 0.001 .mu.m, and still more preferably in a range of
0.1 .mu.m to 0.001 .mu.m. The filtration process may be carried out
by performing a multi-stage process of sending the varnish from a
filter having a large pore diameter to a filter having a small pore
diameter or a single process of directly sending the varnish to a
filter having a small pore diameter. Examples of the material of
the filter include organic materials such as
polytetrafluoroethylene (PTFE), polypropylene (PP), polyether
sulfone (PES), and cellulose; and inorganic materials such as glass
fibers and metals, and the material can be selected in
consideration of the varnish characteristics and the process
adaptability as long as the material does not affect the function
as the underlayer film.
[0186] Further, examples of the method of sending the varnish to
the filter include a method of using a pressure difference and a
method of sending the varnish to the filter using mechanical drive
through a screw or the like. In addition, the temperature for the
filtration can be selected in consideration of the filter
performance, the solution viscosity, and the solubility of the
polymer, and the temperature thereof is preferably in a range of
-10.degree. C. to 200.degree. C., more preferably in a range of
0.degree. C. to 150.degree. C., and still more preferably in a
range of room temperature to 100.degree. C. The temperature thereof
can be selected in consideration of the varnish characteristics or
the process adaptability unless precipitation or gelation of
dissolved components and the like, or modification of the
composition such as thermal decomposition or the like due to
heating is found.
[0187] <Resist Underlayer Film and Method of Producing Resist
Underlayer Film>
[0188] The resist underlayer film according to the present
embodiment can be formed using the material for forming an
underlayer film according to the present embodiment.
[0189] The method of producing the resist underlayer film according
to the present embodiment includes a step of forming a coating film
containing the material for forming an underlayer film according to
the present embodiment on the substrate (hereinafter, also referred
to as a "coating film forming step").
[0190] Further, the method may further include a step of heating
the coating film (hereinafter, also referred to as a "baking step")
as necessary.
[0191] According to the method of producing the resist underlayer
film according to the present embodiment, since the material for
forming an underlayer film according to the present embodiment is
used, a resist underlayer film having sufficient optical
characteristics, etching resistance, excellent flatness, and a
suppressed generation of volatile components can be obtained.
[0192] Further, the material for forming an underlayer film
according to the present embodiment has an excellent embedding
property with respect to the substrate having a complicated shape.
Therefore, according to the method of producing the resist
underlayer film according to the present embodiment, a resist
underlayer film having sufficient optical characteristics, etching
resistance, excellent flatness, and a suppressed generation of
volatile components can be prepared on a substrate having a
complicated shape, such as a substrate having a stepped portion or
a substrate having a plurality of trenches.
[0193] Hereinafter, each step will be described, but the present
invention is not limited thereto.
[0194] [Coating Film Forming Step]
[0195] In the present step, a coating film containing the material
for forming an underlayer film according to the present embodiment
is formed on the substrate using the material for forming an
underlayer film according to the present embodiment.
[0196] Examples of the substrate include a silicon wafer, an
aluminum wafer, and a nickel wafer. An uneven structure may be
imparted to a surface of the substrate. The uneven structure may be
in a state in which a coating film is formed of a low dielectric
material such as a silica (SiO.sub.2) film, a SiCN film, a SiOC
film obtained by doping silica (SiO.sub.2) with carbon (C), a
methylsiloxane-based organic film (SOG), or a silica insulating
film in which minute holes having a diameter of several nanometers
or less are uniformly distributed. As described above, according to
the method of forming the resist underlayer film according to the
present embodiment, a substrate having a stepped portion or a
substrate having a plurality of trenches can be suitably used as
the substrate. Therefore, a resist underlayer film having excellent
flatness can be formed even in a case where a substrate having such
a complicated shape is used.
[0197] As the substrate having a plurality of trenches, for
example, a substrate having different aspect ratios can also be
suitably used. A substrate having various aspect ratios can be
used. For example, in the trenches of the substrate, the ratio
between the maximum value and the minimum value among the aspect
ratios is preferably in a range of 1 to 30, more preferably in a
range of 1 to 25, and still more preferably in a range of 1 to
20.
[0198] The method of coating the substrate with the material for
forming an underlayer film according to the present embodiment is
not particularly limited, and examples thereof include a method of
coating the substrate with the above-described varnish-like
material for forming an underlayer film using a method such as spin
coating, solution cast coating, roll coating, slit coating, or ink
jet coating. As the film thicknesses of the resist underlayer film
from the bottoms of recesses to the atmospheric surface, which is
formed here, the average value Hav described above is preferably in
a range of 5 to 2000 nm, more preferably in a range of 7 to 1000
nm, and still more preferably in a range of 10 to 500 nm. Further,
the lower limit of the film thickness is preferably 15 nm or
greater.
[Baking Step]
[0199] In the present step, the coating film formed in the coating
film forming step is heated (baked). As a method of baking this
coating film, a method of heating the coating film is exemplified.
The temperature of heating the coating film is preferably in a
range of 100.degree. C. to 400.degree. C., more preferably in a
range of 150.degree. C. to 300.degree. C., and still more
preferably in a range of 180.degree. C. to 250.degree. C. The
heating time is preferably in a range of 5 seconds to 60 minutes,
more preferably in a range of 10 seconds to 10 minutes, and still
more preferably in a range of 30 seconds to 3 minutes. The coating
film may be heated in an air atmosphere or an inert gas atmosphere
such as nitrogen gas or argon gas.
[0200] Further, examples of the heating mode in the present step
include a mode in which the coating film is heated for the purpose
of removing a solvent in the coating film, the coating film is
allowed to flow by being heated thereafter and the coating film is
embedded in the uneven structure of the substrate; a mode in which
a foreign substance such as a thermosetting material mixed for the
purpose of compensating for the function while still achieving the
object of the present invention is cured, the coating film is
allowed to flow by being heated thereafter, and the coating film is
embedded in the uneven structure of the substrate; and a mode in
which the coating film is heated for the purpose of separating a
leaving group in the material for forming an underlayer film, the
coating film is allowed to flow by being heated thereafter, and the
coating film is embedded in the uneven structure of the
substrate.
[0201] The coating film may be heated in the baking step by
performing a multi-stage process of increasing the temperature in a
stepwise manner.
[0202] The average value Hay of the film thicknesses of the formed
resist underlayer film is preferably in a range of 5 to 1000 nm,
more preferably in a range of 5 to 800 nm, still more preferably in
a range of 5 to 600 nm, even still more preferably in a range of 5
to 500 nm, even still more preferably 7 to 450 nm, and even still
more preferably in a range of 10 to 400 nm. Further, the lower
limit of the average value Hay of the film thicknesses of the
resist underlayer film is preferably 5 nm or greater, more
preferably 7 nm or greater, and still more preferably 10 nm or
greater, and the upper limit thereof is preferably 1000 nm or less,
more preferably 800 nm or less, still more preferably 600 nm or
less, even still more preferably 500 nm or less, even still more
preferably 450 nm or less, and even still more preferably 400 nm or
less.
[0203] The resist underlayer film according to the present
embodiment can be used as a step member for forming a pattern using
photolithography.
<Laminate>
[0204] The laminate according to the present embodiment includes a
substrate (a) and a resist underlayer film (b) containing the
material for forming an underlayer film according to the present
embodiment which has been formed on one surface of the
substrate.
[0205] It is preferable that the laminate has a structure in which
the substrate (a) is in contact with the resist underlayer film
(b).
[0206] Here, the resist underlayer film (b) and the method of
producing the resist underlayer film are the same as the resist
underlayer film and the method of producing the resist underlayer
film according to the present embodiment, and thus the description
thereof will not be repeated.
[0207] FIG. 2 are schematic views for describing the film thickness
4 of the resist underlayer film 2, the height 5 of the uneven
structure 7, and the interval 6 between projections of the uneven
structure 7 in the laminate 10 according to the embodiment of the
present invention.
[0208] The substrate (a) may be a structure having a flat surface,
but it is preferable that one or both surfaces thereof have an
uneven structure with a height of preferably 5 to 500 nm, more
preferably 7 to 450 nm, and still more preferably 10 to 400 nm.
[0209] Here, the above-described height indicates the height 5 of
the uneven structure 7 shown in FIG. 2. For example, optional ten
heights 5 of the uneven structure 7 are measured, and the average
value of these heights can be employed as the height.
[0210] Further, the interval between projections in the uneven
structure is preferably greater than or equal to 1 nm and less than
or equal to 10 mm. The lower limit of the interval between
projections in the uneven structure is more preferably 3 nm or
greater, more preferably 5 nm or greater, and particularly
preferably 10 nm or greater.
[0211] Here, the interval between projections in the uneven
structure indicates the interval 6 between projections in the
uneven structure 7 shown in FIG. 2. For example, optional ten
intervals 6 between projections in the uneven structure 7 are
measured, and the average value of these intervals can be employed
as the interval.
[0212] Further, the upper limit of the interval between projections
in the uneven structure is more preferably 5 mm or less, more
preferably 1 mm or less, and particularly preferably 0.5 mm or
less.
[0213] From the viewpoint that the effects of the resist underlayer
film (b) tend to be significantly exhibited, it is preferable that
the substrate (a) has the above-described uneven structure.
[0214] The thickness of the substrate (a) is preferably in a range
of 0.01 to 10000 .mu.m. The lower limit of the thickness of the
substrate (a) is more preferably 0.03 .mu.m or greater, still more
preferably 0.05 .mu.m or greater, and particularly preferably 0.10
.mu.m or greater.
[0215] The upper limit of the thickness of the substrate (a) is
more preferably 5000 .mu.m or less, still more preferably 3000
.mu.m or less, and particularly preferably 1000 .mu.m or less.
[0216] In the laminate according to the present embodiment, the
flatness (.DELTA.FT) of the surface (.alpha.) of the resist
underlayer film (b) on a side opposite to the substrate (a) which
is calculated by the following equation is preferably in a range of
0% to 5%, more preferably in a range of 0% to 3%, and still more
preferably 0% to 1%.
Flatness(.DELTA.FT)=[(H.sub.max-H.sub.min)/H.sub.av].times.100(%)
[0217] Here, the film thicknesses of the resist underlayer film (b)
are measured in ten optional sites of the surface (.alpha.), the
average value of these measured values is set as H.sub.av, the
maximum value in the film thicknesses of the resist underlayer film
(b) is set as H.sub.max, and the minimum value in the film
thicknesses of the resist underlayer film (b) is set as
H.sub.min.
[0218] In this manner, the thickness of the resist layer can be
made more uniform regardless of the presence of the intermediate
layer, and a desired pattern in lithography can be obtained with
excellent reproducibility.
<Pattern Formation Method>
[0219] A pattern formation method according to the present
embodiment includes a step of forming a resist pattern on an upper
surface side of the resist underlayer film according to the present
embodiment (hereinafter, also referred to as a "resist pattern
forming step"); and a step of sequentially etching the resist
underlayer film and the substrate using the resist pattern as a
mask (hereinafter, also referred to as an "etching step").
[0220] Further, the pattern formation method according to the
present embodiment may be performed by forming an intermediate
layer on an upper surface side of the resist underlayer film to
form a resist pattern on an upper surface side of the intermediate
layer in the resist pattern forming step and etching the
intermediate layer in the etching step.
[0221] According to the pattern formation method according to the
present embodiment, an excellent pattern can be formed because the
resist underlayer film according to the present embodiment which
has sufficient optical characteristics, etching resistance,
excellent flatness, and a suppressed generation of volatile
components is used.
[0222] Hereinafter, each step will be described, but the present
invention is not limited thereto.
[Resist Pattern Forming Step]
[0223] In the present step, a resist pattern is formed on the upper
surface side of the resist underlayer film. An intermediate layer
is formed on the upper surface side of the resist underlayer film,
and the resist pattern is formed on the upper surface side of this
intermediate layer.
[0224] The intermediate layer indicates a layer that compensates
for the functions of the resist underlayer film and/or the resist
film or has these functions for imparting the functions that the
resist underlayer film and/or the resist film does not have in the
formation of the resist pattern or the like. For example, in a case
where an anti-reflection film (also referred to as an
anti-reflection layer) is formed as an intermediate layer, the
intermediate layer can compensate for the anti-reflection function
of the resist underlayer film. Further, in a case where a hard mask
layer is formed as an intermediate layer, the influence on the
resist underlayer film in case of using an alkali developer during
a developing step is suppressed and/or the insufficient etching
resistance of the resist pattern formation layer in case of etching
the substrate formed of silicon, aluminum, nickel, and the like of
the lower layer after etching the underlayer film according to the
present embodiment can be compensated.
[0225] Further, the intermediate layer formed on the underlayer
film according to the present embodiment may include one or both of
the anti-reflection layer and the hard mask layer, and the layers
may be configured such that the anti-reflection layer or the hard
mask layer is formed directly on the underlayer film according to
the present embodiment. The layer configuration is suitably
selected in consideration of the characteristics of the resist
material and the processed substrate material and the
productivity.
[0226] The intermediate layer can be formed of an organic compound
or an inorganic oxide. Examples of the organic compound include
DUV-42, DUV-44, ARC-28, and ARC-29 (all manufactured by Brewer
Science, Inc.); and AR-3 and AR-19 (both manufactured by Rohm and
Haas Company). Further, as the inorganic oxide, NFC SOG Series
(manufactured by JSR Corporation), and polysiloxane, titanium
oxide, alumina oxide, and tungsten formed using a CVD method oxide
can be used.
[0227] The method of forming the intermediate layer is not
particularly limited, and examples thereof include a coating method
and a CVD method. Among these, a coating method is preferable. In a
case of using the coating method, the intermediate layer can be
continuously formed after formation of the resist underlayer
film.
[0228] Further, the film thickness of the intermediate layer is not
particularly limited and can be appropriately selected depending on
the function required for the intermediate layer, and the film
thickness thereof is preferably in a range of 1 nm to 5 .mu.m, more
preferably in a range of 5 nm to 3 .mu.m, and still more preferably
in a range of 10 nm to 0.3 .mu.m.
[0229] Examples of the method of forming the resist pattern on the
upper surface side of the resist underlayer film or the
intermediate layer include a method of using photolithography. This
method will be described in detail layer, and the present invention
is not limited thereto.
[0230] The method of using photolithography includes a step of
forming a resist film on the upper surface side of the resist
underlayer film using a resist composition or the like
(hereinafter, also referred to as a "resist film forming step"); a
step of exposing the resist film (hereinafter, also referred to as
an "exposing step"), and a step of developing the exposed resist
film (hereinafter, also referred to as a "developing step").
[0231] (Resist Film Forming Step)
[0232] In the present step, the resist film is formed on the upper
surface side of the resist underlayer film.
[0233] Specifically, the resist film is formed by coating the
surface with the resist composition such that the obtained resist
film has a predetermined film thickness and allowing the solvent in
the coating film to volatilize by performing pre-baking.
[0234] Examples of the resist composition include a positive type
or negative type chemically amplified resist composition containing
a photoacid generator; a positive type resist composition formed of
an alkali-soluble resin and a quinone diazide-based photosensitive
agent; and a negative type resist composition formed of an
alkali-soluble resin and a crosslinking agent.
[0235] The solid content concentration of the resist composition is
preferably in a range of 0.1% by mass to 50% by mass, more
preferably in a range of 0.5% by mass to 50% by mass, and still
more preferably in a range of 1.0% by mass to 50% by mass, and the
solid content concentration thereof can be selected to be in an
appropriate range in consideration of the target film thickness and
the productivity.
[0236] Further, it is preferable that the resist composition is
prepared by being filtered through a filter having a pore diameter
of approximately 0.1 .mu.m. Further, in this step, a commercially
available resist composition can be used as it is. The method of
coating the surface with the resist composition is not particularly
limited and can be performed using a spin coating method, a cast
coating method, or a roll coating method.
[0237] Further, the pre-baking temperature is appropriately
selected depending on the kind of the resist composition to be
used, but is preferably in a range of 30.degree. C. to 200.degree.
C. and more preferably in a range of 50.degree. C. to 150.degree.
C.
[0238] (Exposing Step)
[0239] In the present step, the resist film formed in the resist
film forming step is exposed. The resist film is exposed through,
for example, a predetermined mask pattern and liquid immersion as
necessary.
[0240] The exposure light is appropriately selected from
electromagnetic waves such as visible light, ultraviolet rays, deep
ultraviolet rays, X rays, and .gamma. rays; and particle beams such
as electron beams, molecular beams, ion beams, and a rays depending
on the kind of the photoacid generator used in the resist
composition. In addition, deep ultraviolet rays are preferable; KrF
excimer laser light (248 nm), ArF excimer laser light (193 nm), F2
excimer laser light (wavelength of 157 nm), Kr2 excimer laser light
(wavelength of 147 nm), ArKr excimer laser light (wavelength of 134
nm), or extreme ultraviolet rays (wavelength of 13 nm and the like)
are more preferable, and ArF excimer laser light is still more
preferable.
[0241] After the exposure, post-baking can be performed in order to
improve the resolution, the pattern profile, and the developability
of the resist pattern to be formed.
[0242] The post-baking temperature is appropriately adjusted
depending on the kind of the resist composition to be used, but is
preferably in a range of 50.degree. C. to 200.degree. C. and more
preferably in a range of 70.degree. C. to 150.degree. C.
[0243] (Developing Step)
[0244] In the present step, the resist film exposed in the exposing
step is developed.
[0245] The developer used in the development is appropriately
selected depending on the kind of the resist composition to be
used. In a case of alkali development, examples of the developer
include an alkaline aqueous solution such as sodium hydroxide,
potassium hydroxide, sodium carbonate, sodium silicate, sodium
metasilicate, ammonia, ethylamine, n-propylamine, diethylamine,
di-n-propylamine, trimethylamine, methyl diethylamine, dimethyl
ethanolamine, triethanolamine, tetramethyl ammonium hydroxide,
tetraethyl ammonium hydroxide, pyrrole, piperidine, choline,
1,8-diazabicyclo[5.4.0]-7-undecene, or
1,5-diazabicyclo[4.3.0]-5-nonene. Further, in a case where the
intermediate layer is formed by performing the intermediate layer
forming step, the influence on the resist underlayer film of any of
these alkaline aqueous solutions can be suppressed.
[0246] An appropriate amount of a surfactant or a water-soluble
organic solvent such as methanol or ethanol can be added to these
alkaline aqueous solutions.
[0247] Further, a developer containing an organic solvent can be
used as the developer. Examples of the organic solvent include
esters, ketones, ethers, alcohols, amides, and hydrocarbons. The
solvent used in the organic solvent development is appropriately
selected depending on the characteristics of the resist underlayer
film.
[0248] After the development using the developer, a predetermined
resist pattern is formed by performing washing and drying on the
resist film.
[0249] Further, as the method of performing the resist pattern
forming step, a method of using a nanoimprint method or a method of
using a self-assembled composition can be used in addition to the
method of using photolithography described above.
[0250] [Etching Step]
[0251] In this step, the resist underlayer film and the substrate
are sequentially etched using the resist pattern as a mask. In this
manner, the pattern is formed on the substrate. Further, in a case
of forming an intermediate layer, the intermediate layer is also
etched.
[0252] The above-described etching may be dry etching or wet
etching. The dry etching can be performed using a known dry etching
device. In addition, the source gas at the time of dry etching is
not particularly limited because the source gas depends on the
elemental composition of the material to be etched, and examples of
the source gas include gas containing an oxygen element such as
O.sub.2, CO, or CO.sub.2; inert gas such as H.sub.e, N.sub.2, or
Ar; chlorine-based gas such as Cl.sub.2 or BCl.sub.3;
fluorine-based gas such as CHF.sub.3 or CF.sub.4; and gas such as
H.sub.2 or NH.sub.3. Further, these gases can be used by being
mixed.
[Method of Removing Underlayer Film Material after Formation of
Substrate Pattern]
[0253] In the present step, the resist underlayer film which
becomes unnecessary is removed after the resist pattern is
transferred to the substrate and formed thereon in the etching
step.
[0254] The removal method may be a dry method or a wet method using
a solvent or the like and is suitably selected in consideration of
the physical properties of the material and the process
adaptability. Further, a combination of the dry method and the wet
method may be used as the removal method.
[0255] In a case of the dry method, a dry etching device used in
the etching step can be used. Accordingly, the dry method is
preferable used from the viewpoint of the productivity since there
is no need to change the production line at the time of transition
from the etching step to the step of removing the underlayer film
material.
[0256] In the step of removing the underlayer film material, the
source gas at the time of using a dry etching device is suitably
selected depending on the elemental composition of the material to
be etched, and examples of the source gas include gas containing an
oxygen element such as O.sub.2, CO, or CO.sub.2; inert gas such as
H.sub.e, N.sub.2, or Ar; chlorine-based gas such as Cl.sub.2 or
BCl.sub.3; fluorine-based gas such as CHF.sub.3 or CF.sub.4; and
gas such as H.sub.2 or NH.sub.3. The gas source is suitably
selected depending on the substrate material or the low dielectric
material applied to the surface of the substrate. Further, these
gases can be used in the form of a mixture of two or more kinds
thereof.
[0257] [Second Invention]
[0258] Hereinafter, an embodiment according to the second invention
will be described.
<Material for Forming Underlayer Film>
[0259] A material for forming an underlayer film according to the
present embodiment is a material for forming an underlayer film
which is used to form a resist underlayer film used in a
multi-layer resist process. Further, the material for forming an
underlayer film contains a cyclic olefin polymer, and the residual
film rate of the material for forming an underlayer film which is
measured using the following method 4 is greater than or equal to
50% and less than or equal to 100% and preferably greater than or
equal to 60% and less than or equal to 100%. The lower limit of the
residual film rate of the material for forming an underlayer film
is more preferably 70% or greater. In addition, the upper limit of
the residual film rate of the material for forming an underlayer
film is more preferably 99% or less and still more preferably 98%
or less. As described above, in a case where the residual film rate
is extremely low, defects caused by mixing with the intermediate
layer may occur. Meanwhile, in a case where the residual film rate
is slightly lower than 100%, a moderate degree of entanglement of
polymers forming the intermediate layer and the base film occurs so
that the peeling strength is increased in some cases.
[0260] Method 4: A coating film which is formed of the material for
forming an underlayer film according to the present embodiment and
has a thickness (a) of greater than or equal to 200 nm and less
than or equal to 500 nm is formed on a silicon wafer. Next, the
obtained coating film is treated at 200.degree. C. for 10 minutes.
Next, the coating film is immersed in propylene glycol-1-monomethyl
ether-2-acetate at 23.degree. C. for 10 minutes and dried under
conditions of 150.degree. C. for 3 minutes so that a remaining
solvent in the coating film is removed. Next, the thickness
(.beta.) of the coating film obtained by removing the remaining
solvent is measured, and the residual film rate
(=.beta./.alpha..times.100) (%) is calculated.
[0261] Further, the material for forming an underlayer film
according to the present embodiment is a material for forming an
underlayer film which is used to form a resist underlayer film used
in a multi-layer resist process. Further, the material for forming
an underlayer film is a material of a film containing a cyclic
olefin polymer, the cyclic olefin polymer is soluble in an organic
solvent at any concentration of at least greater than or equal to
0.01% by mass and less than or equal to 50% by mass, and a residual
film rate of the cyclic olefin polymer in the film which is
measured using the following method 4 is greater than or equal to
50% and less than or equal to 100% and preferably greater than or
equal to 60% and less than or equal to 100%. The lower limit of the
residual film rate of the cyclic olefin polymer is more preferably
70% or greater. In addition, the upper limit of the residual film
rate of the cyclic olefin polymer is more preferably 99% or less
and still more preferably 98% or less. As described above, in a
case where the residual film rate is extremely low, defects caused
by mixing with the intermediate layer may occur. Meanwhile, in a
case where the residual film rate is slightly lower than 100%, a
moderate degree of entanglement of polymers forming the
intermediate layer and the base film occurs so that the peeling
strength is increased in some cases.
[0262] Method 4: A coating film which is formed of the cyclic
olefin polymer according to the present embodiment and has a
thickness (c) of greater than or equal to 200 nm and less than or
equal to 500 nm is formed on a silicon wafer. Next, the obtained
coating film is treated at 200.degree. C. for 10 minutes. Next, the
coating film is immersed in propylene glycol-1-monomethyl
ether-2-acetate at 23.degree. C. for 10 minutes and dried under
conditions of 150.degree. C. for 3 minutes so that a remaining
solvent in the coating film is removed. Next, the thickness
(.beta.) of the coating film obtained by removing the remaining
solvent is measured, and the residual film rate
(=.beta./.alpha..times.100) (%) is calculated.
[0263] Here, as a condition for treating the peeled film at a high
temperature, it is more preferable that the peeled film is treated
at 200.degree. C. for 30 minutes.
[0264] The residual film rate according to the method 4 indicates
the solubility of the film in a solvent. There is a tendency that
the film is unlikely to be dissolved in a solvent as the value
increases.
[0265] As described above, in a case where a circuit diagram is
drawn using the line width less than or equal to the wavelength of
exposure light, a method of forming a plurality of uneven layers
and combining the layers has been known. In order to realize such a
mode, a method of forming an intermediate layer on a resist
underlayer film for the purpose of smoothing the uneven layers and
forming a new resist layer thereon can be exemplified.
[0266] According to the examination conducted by the present
inventors, for example, in a case where this intermediate layer is
formed according to a spin coating method or the like, a wrong
choice of a solvent may lead to intermixing of the resist
underlayer film with the intermediate film. As the result, it was
found that the interface strength between the underlayer film and
the intermediate layer may be degraded or the smoothness of the
underlayer film may be lost.
[0267] The present inventors repeatedly conducted examination in
order to solve the above-described problems. As the result, it was
found that occurrence of intermixing of the resist underlayer film
with the intermediate layer can be suppressed in a case where the
resist underlayer film has a low affinity for the solvent used for
formation of the intermediate layer.
[0268] The present inventors repeatedly conducted examination based
on the above-described knowledge. As the result, it was found for
the first time that dissolution of the resist underlayer film or
mixing of the resist underlayer film with the intermediate layer
more than necessary can be effectively suppressed by using the
material for forming an underlayer film or the cyclic olefin
polymer whose residual film rate at the time of being immersed in
propylene glycol-1-monomethyl ether-2-acetate, which is measured
according to the method 4, is in the above-described range.
[0269] In other words, in a case where the residual film rate of
the material for forming an underlayer film or the cyclic olefin
polymer according to the present embodiment which is measured
according to the method 4 is greater than or equal to the
above-described lower limit, dissolution of the resist underlayer
film or mixing of the resist underlayer film with the intermediate
layer more than necessary can be suppressed at the time of forming
the intermediate layer on the resist underlayer film. As the
result, a laminate having excellent adhesiveness between the
intermediate layer and the resist underlayer film and excellent
flatness can be realized.
[0270] The cyclic olefin polymer used in the second invention is
not particularly limited as long as the polymer is dissolved in an
organic solvent in a temperature range of room temperature to
50.degree. C. and preferably at room temperature. As the organic
solvent, a solvent selected from the group consisting of an
alcohol-based solvent, an ether-based solvent, a ketone-based
solvent, an amide-based solvent, an ester-based solvent, and a
cyclic hydrocarbon-based solvent is preferable. Among these, an
alcohol-based solvent, an ether-based solvent, a ketone-based
solvent, an amide-based solvent, or an ester-based solvent is more
preferable, and an ether-based solvent, a ketone-based solvent, an
amide-based solvent, or an ester-based solvent is still more
preferable. A solvent having a polyether monoester structure is
particularly preferable.
[0271] More specific preferred examples of the cyclic olefin
polymer of the second invention include a cyclic olefin polymer
having a norbornane skeleton or a tetracyclododecane skeleton.
Further, it is preferable that the cyclic olefin polymer has a
substituent having heteroatoms contained in the above-described
organic solvent. Preferred examples of the substituent having
heteroatoms include an alkoxy group, an aryloxy group, an
alkoxyalkyl group, an aryloxyalkyl group, an alkoxycarbonyl group,
a dialkylaminocarbonyl group, an aryloxycarbonyl group, an
alkylarylaminocarbonyl group, an alkoxycarbonylalkyl group, an
alkoxycarbonylaryl group, an aryloxycarbonylalkyl group, an
alkoxyalkyloxycarbonyl group, and an alkoxycarbonylalkyloxycarbonyl
group. As the substituent, the above-described ester groups are
particularly preferable.
[0272] Other specific preferred examples of the cyclic olefin
polymer used in the second invention include a cyclic olefin
polymer having the structural unit [A] and the structural unit [B]
disclosed in the first invention. The preferable conditions such as
the proportions of these structural units are the same as those
disclosed in the first invention.
[0273] A known method can be used as the method of forming a film
using the material for forming an underlayer film according to the
present embodiment. Specific preferred examples thereof include a
spin coating method. As the solvent that forms a polymer solution
used for spin coating, the above-described solvent for spin coating
can be exemplified. Particularly preferred examples thereof include
polyether ester or polyether such as the above-described PGMEA,
ketone, alcohol, and ester. In consideration of the solubility or
the drying step after film formation, a mode of containing a
solvent having a cyclic structure is preferable in some cases.
Specifically, a cyclic ketone compound such as cycloalkanone is
exemplified, and cyclohexanone is preferable.
[0274] It is desirable that the material for forming an underlayer
film according to the present embodiment is treated at a high
temperature for a predetermined time. Specifically, a temperature
range of 100.degree. C. to 400.degree. C. can be exemplified as the
temperature condition. The lower limit of the temperature is
preferably 150.degree. C. or higher and more preferably 180.degree.
C. or higher. Meanwhile, the upper limit of the temperature is
preferably 300.degree. C. or lower and more preferably 250.degree.
C. or lower. Based on this reason, the present inventors speculated
as follows.
[0275] According to the examination conducted by the present
inventors, the film formed using the cyclic olefin polymer
containing a polar group according to the present embodiment is in
the form in which a relatively uniform change in polarity occurs in
the entire heated portion by the heat treatment. It is considered
that the solubility in a solvent is greatly changed, in other
words, the film is unlikely to be dissolved in the organic solvent
due to the change of the polarity. According to the present
inventors, it is considered that the above-described change may be
caused by the change of properties of the polar group in the cyclic
olefin polymer according to the present embodiment. The possibility
that the change is caused by a pseudo-crosslinked structure or a
crosslinked structure being employed. For example, the
configuration having the structure represented by Formula (2) is a
preferable aspect and the effects are high. Hereinafter, the
description will be provided in more detail.
[0276] In order to change the polarity of the film containing the
cyclic olefin polymer according to the present embodiment, it is
important that the polymer contains one or two repeating structural
units [B] represented by Formula (2) in some cases. In a case where
the repeating structural unit [B] represented by Formula (2) is
heated, this causes cleavage of an ether group and a thioether
group so that the polarity of a molecule can be changed.
[0277] As another aspect, in a case where at least one of R.sup.1
to R.sup.8 contains an alkoxycarbonyl group, an alkoxycarbonylalkyl
group, an alkoxycarbonylaryl group, or an
alkoxycarbonylalkyloxycarbonyl group and preferably one or more of
alkoxycarbonyl groups in which tertiary carbons are bonded to form
an ester group, alkoxycarbonylalkyl groups, alkoxycarbonylaryl
groups, alkoxycarbonylalkyloxycarbonyl groups, or
alkoxyalkyloxycarbonyl groups, generation of a carboxyl group due
to heating can be expected to be led to a large change in polarity
of a molecule.
[0278] Since the aspect of the present invention has such
characteristics, as described above, it is considered that a
sufficiently high intermixing resistance effect can be exhibited
even in a case where the content of the crosslinking agent is
decreased.
[0279] The material for forming an underlayer film according to the
present embodiment is a material for forming a layer disposed
between an intermediate layer and a substrate (preferably a
substrate having an uneven structure) in a step of manufacturing a
semiconductor device. The layer disposed between the intermediate
layer and the substrate is referred to as a resist underlayer film
based on a resist layer formed of a resist material that typically
transfers a mask pattern in a photolithography process. The surface
of the substrate which comes into contact with the resist
underlayer film may be in a state in which a coating film is formed
of a low dielectric material, such as a silica (SiO.sub.2) film, a
SiCN film, a SiOC film obtained by doping silica (SiO.sub.2) with
carbon (C), a methylsiloxane-based organic film (SOG), or a silica
insulating film in which minute holes having a size of several
nanometers or less are uniformly distributed.
[0280] The intermediate layer indicates a layer that compensates
for the functions of the resist underlayer film and/or the resist
film or has these functions for imparting the functions that the
resist underlayer film and/or the resist film does not have in the
formation of the resist pattern or the like. For example, in a case
where an anti-reflection film (also referred to as an
anti-reflection layer) is formed as an intermediate layer, the
intermediate layer can compensate for the anti-reflection function
of the resist underlayer film. Further, in a case where a hard mask
layer is formed as an intermediate layer, the influence on the
resist underlayer film in case of using an alkali developer during
a developing step is suppressed and/or the insufficient etching
resistance of the resist pattern formation layer at the time of
etching the substrate formed of silicon, aluminum, nickel, and the
like of the lower layer after etching the underlayer film according
to the present embodiment can be compensated.
[0281] Further, the intermediate layer formed on the underlayer
film according to the present embodiment may include one or both of
the anti-reflection layer and the hard mask layer, and the layers
may be configured such that the anti-reflection layer or the hard
mask layer is formed directly on the underlayer film according to
the present embodiment. The layer configuration is suitably
selected in consideration of the characteristics of the resist
material and the processed substrate material and the
productivity.
[0282] The intermediate layer can be formed of an organic compound
or an inorganic oxide. Examples of the organic compound include
DUV-42, DUV-44, ARC-28, and ARC-29 (all manufactured by Brewer
Science, Inc.); and AR-3 and AR-19 (both manufactured by Rohm and
Haas Company). Further, as the inorganic oxide, NFC SOG Series
(manufactured by JSR Corporation), and polysiloxane, titanium
oxide, alumina oxide, and tungsten formed using a CVD method oxide
can be used.
[0283] As the method of forming the intermediate layer, a coating
method is preferable. In a case of using the coating method, the
intermediate layer can be continuously formed after formation of
the resist underlayer film.
[0284] As the solvent used for forming the intermediate layer
according to the coating method, those exemplified as the solvents
for a spin coating solution are preferable. Among these, polyether
or polyether ester such as PGMEA is preferable.
[0285] Further, the film thickness of the intermediate layer is not
particularly limited and can be appropriately selected depending on
the function required for the intermediate layer, and the film
thickness thereof is preferably in a range of 1 nm to 5 .mu.m, more
preferably in a range of 5 nm to 3 .mu.m, and still more preferably
in a range of 10 nm to 0.3 .mu.m.
[0286] As a preferable cyclic olefin polymer related to the
material for forming an underlayer film according to the present
embodiment, the same polymer as the cyclic olefin polymer according
to the first invention as described above can be used.
[0287] Therefore, detailed description will not be provided.
[0288] The resist underlayer film, the method of forming a resist
underlayer film, and the pattern formation method according to the
present embodiment are based on the resist underlayer film, the
method of forming a resist underlayer film, and the pattern
formation method according to the first invention. Therefore,
detailed description will not be provided.
[0289] Hereinbefore, the embodiments of each of the inventions have
been described, but these are merely examples of the present
invention and various other configurations can be employed.
[0290] Further, the present invention is not limited to the
above-described embodiments, and modifications, improvements, and
the like for achieving the purpose of the present invention are
included in the present invention.
[0291] Further, the above-described present inventions can be
combined as long as the contents do not contradict each other.
EXAMPLES
[0292] Hereinafter, the present embodiment will be described in
detail with reference to examples and comparative examples. The
present embodiment is not limited to the description of these
examples.
[0293] The method of analyzing polymers in the examples and
comparative examples and the methods of evaluating the embedding
property and the flatness are as follows.
[Weight-Average Molecular Weight (Mw) and Molecular Weight
Distribution (Mw/Mn)]
[0294] The weight-average molecular weight (Mw) and the number
average molecular weight (Mn) of the polymer dissolved in
tetrahydrofuran (THF) or trifluorotoluene (TFT) were measured using
gel permeation chromatography (GPC) under the following conditions
and calculated by calibrating the molecular weight based on
polystyrene standards.
[0295] Detector: RI-2031 and 875-UV (manufactured by JASCO
Corporation) or Model 270 (manufactured by Viscotec GmbH.),
Serially connected column: Shodex K-806M, 804, 803, 802.5, Column
temperature: 40.degree. C., flow rate: 1.0 ml/min, sample
concentration: 3.0 to 9.0 mg/ml
[Measurement of Hydrogenation Ratio]
[0296] A polymer sample was dissolved in deuterated chloroform, and
the integral value of a peak belonging to hydrogen of double bond
carbon in a range of a chemical shift 5 of 5.0 to 7.0 ppm under
conditions of 270 MHz and the 1H-NMR spectrum.
[Glass Transition Temperature]
[0297] The glass transition temperature was measured by heating a
measurement sample at a heating rate of 10.degree./C in a nitrogen
atmosphere using DSC-50 (manufactured by Shimadzu Corporation).
[Method of Evaluating Volatile Component]
[0298] A THF solution of a polymer with a concentration of 20% by
mass was weighed using an aluminum plate having a diameter of 5 mm
such that the weight thereof was adjusted to 30 mg to 50 mg, and
baked at 200.degree. C. for 3 minutes in a nitrogen flow to remove
THF. Next, the resultant was cooled to room temperature, and the
weight thereof (W.sub.0) was measured. Using a sample in a state in
which a resin was solidified, the sample was heated to 30.degree.
C. to 300.degree. C. at a heating rate of 10.degree. C./min using
TGA-60 (manufactured by Shimadzu Corporation) in a nitrogen
atmosphere, and the weight thereof was continuously measured along
with an increase in temperature to obtain the temperature vs.
weight chart. Here, a weight reduction amount (W.sub.1) in a
temperature range of 100.degree. C. to 250.degree. C. was read from
the chart, and the amount of volatile components was calculated
based on the following equation.
Amount of volatile components (% by
mass)=W.sub.1/W.sub.0.times.100
[Measurement of Solid Viscoelasticity]
[0299] The solid viscoelasticity was measured under conditions of a
measurement temperature range of 30.degree. C. to 300.degree. C., a
heating rate of 3.degree. C./min, and a frequency of 1 Hz in a
nitrogen atmosphere in a shear mode using MCR302 (rheometer)
(manufactured by Anton Paar GmbH). More specifically, the
measurement was carried out according to the following method.
[0300] First, white powder (10 mg) of the cyclic olefin polymer
according to the present embodiment was placed in the center of a
parallel disk having a diameter of 8 mm which had been heated to
230.degree. C. Next, the powder was interposed using the disk,
melted in a nitrogen atmosphere, and cooled to 30.degree. C.
[0301] Thereafter, the sample was heated to 300.degree. C. at the
above-described heating rate and a frequency of 1 Hz in a shear
mode. A graph was prepared by plotting the relationship between the
obtained heating temperature, the storage modulus (G'), and the
loss modulus (G''), and the temperature of the intersection between
the storage modulus (G') curve and the loss modulus (G'') curve was
confirmed (see FIG. 1).
[Measurement of Residual Film Rate]
[0302] A coating film having a thickness (.alpha.) of nm which was
formed of a cyclic olefin polymer was formed on a silicon wafer.
Next, the obtained coating film was treated at 200.degree. C. for
10 minutes or 30 minutes. After the sample was cooled to room
temperature, the coating film was cut in a size of 20 mm.times.10
mm. This film was immersed in an organic solvent (propylene
glycol-1-monomethyl ether-2-acetate (PGMEA), propylene glycol
monomethyl ether (PGME), or a mixed solvent of PGME and PGMEA at a
mass ratio (PGME/PGMEA) of 7/3) at 23.degree. C. for 10 minutes and
dried under conditions of 150.degree. C. for 3 minutes so that the
residual solvent in the coating film was removed. Next, the
thickness (.beta.) of the coating film from which the residual
solvent had been removed was measured, and the residual film rate
(=.beta./.alpha..times.100) (%) was calculated.
[0303] Here, the coating film was prepared according to the
following method.
[0304] A solution obtained by dissolving the cyclic olefin polymer
according to the present embodiment in an organic solvent (a
solution containing propylene glycol-1-monomethyl ether-2-acetate
(PGMEA) and cyclohexanone at a mass ratio (PGMEA/cyclohexanone) of
5/5) at a concentration of 10% by mass was prepared, and a 4 inch
silicon wafer was spin-coated with 2.5 mL of the obtained solution.
Next, the resulting sample was dried at 120.degree. C. for 1 minute
in a nitrogen atmosphere and then dried in a vacuum at 80.degree.
C. for 5 hours. Subsequently, the sample was cooled to room
temperature and cut in a size of 20 mm.times.20 mm, thereby
obtaining a coating film.
[Substrate Having Surface Provided with Uneven Structure for
Evaluating Embedding Property]
[0305] Substrate A: A silicon substrate having a size of 3
cm.times.3 cm, in which a line and space pattern with a height of
200 nm, a projection width of 40 to 150 nm, and a width between
projections of 40 to 150 nm was formed on the surface of the
substrate was used.
[0306] Substrate B: A silicon substrate having a size of 3
cm.times.3 cm, in which a line and space pattern with a height of
200 nm, a projection width of 40 nm to 1000 .mu.m, and a width
between projections of 40 nm to 1000 .mu.m was formed on the
surface of the substrate was used.
[Evaluation of Embedding Property]
[0307] The steps up to the baking step were performed, and the
sample obtained by forming the resist underlayer film on the uneven
surface of the silicon substrate was divided to expose the surface
for observing the cross section. Thereafter, the embedding property
was evaluated by observing the cross section of the substrate A
having a width between projections of 40 nm or the cross section of
the substrate B having a.sub.1 of 900 .mu.m, b.sub.1 of 1000 nm,
a.sub.2 of 40 nm, and b.sub.2 of 1000 nm using a scanning electron
microscope JSM-6701F (manufactured by JASCO Corporation)
(hereinafter, also noted as a SEM).
[Evaluation of Flatness]
[0308] Ten heights from the bottoms of recesses to the atmospheric
surface in an area with a projection width of 40 nm and a width
between projections of 120 nm from the cross section of the
substrate A whose embedding property was evaluated were measured,
and the average value thereof was set as H.sub.av. Next, the
flatness showing the index of the flatness was calculated using the
following equation based on each of the maximum height (H.sub.max)
and the minimum height (H.sub.min) from the ten measured
heights.
Flatness(.DELTA.FT)=[(H.sub.max-H.sub.min)/H.sub.av].times.100(%)
[0309] Further, ten heights from the bottoms of recesses to the
atmospheric surface in each pattern region of an area having
a.sub.1 of 900 .mu.m, b.sub.1 of 900 .mu.m, a.sub.2 of 40 nm, and
b.sub.2 of 120 nm from the cross section of the substrate B whose
embedding property was evaluated were measured, and the average
value thereof was set as Hay, each of the average value H.sub.1
(a.sub.1 of 900 .mu.m and b.sub.1 of 900 .mu.m), the average value
H.sub.2 (a.sub.2 of 40 nm and b.sub.2 of 120 nm), and the average
value H.sub.3 of H.sub.1 and H.sub.2 was acquired, and the flatness
showing the index of the flatness was calculated using the
following equation.
Flatness(.DELTA.FT)=|H.sub.1-H.sub.2|/H.sub.3.times.100(%)
[Measurement of n Value and k Value]
[0310] The n value and the k value were measured at optional three
points of a measurement sample having a size of 20 mm.times.20 mm,
obtained by being applied to a silicon wafer such that the
thickness thereof was set to 250 nm, in an environment of a
temperature of 23.degree. C. to 25.degree. C. and a humidity of 50%
to 55% using a spectroscopic ellipsometer GES5E (manufactured by
Semilab Inc.). Based on the measurement results, the refractive
indices (n value) and the extinction coefficients (k value) at 193
nm were calculated, and the n value and the k value were
respectively acquired from the three average values.
[0311] Here, the measurement sample was prepared according to the
following method.
[0312] A solution obtained by dissolving the cyclic olefin polymer
according to the present embodiment in a PGMEA at a concentration
of 10% by mass was prepared, and a 4 inch silicon wafer was
spin-coated with the obtained solution. Next, the resulting sample
was baked at 200.degree. C. for 3 minutes in a nitrogen atmosphere.
Subsequently, the sample was cooled to room temperature and cut in
a size of 20 mm.times.20 mm, thereby obtaining a sample for
measurement.
[Evaluation of Plasma Etching Characteristics]
[0313] A parallel plate type plasma treatment device RIH1515Z
(manufactured by ULVAC, Inc.) was used. First, the plasma etching
treatment was performed by placing a sample in a chamber, reducing
the pressure inside the chamber to 1 Pa or less, introducing 30
sccm of CHF.sub.3 gas to the chamber, maintaining the pressure
inside the chamber at 7 Pa, and applying a high frequency powder of
13.56 MHz for plasma discharge. The plasma etching treatment was
performed for 30 seconds, 60 seconds, and 90 seconds.
[Method of Measuring Etching Rate]
[0314] The film thickness of the surface of the etched substrate
was measured at three points using a spectroscopic ellipsometer
GES5E (manufactured by Semilab Inc.), and the film thickness was
calculated from the average value. Next, the amount of decrease in
film thickness due to the etching was calculated from the film
thicknesses before and after the etching, and the time (sec) was
plotted on the horizontal axis and the amount (nm) of the reduced
film thickness was plotted on the vertical axis. The etching rate
(nm/sec) was calculated from the inclination of the obtained
graph.
[Evaluation of Ashing Characteristics Using O.sub.2 Etching]
[0315] The resist underlayer film was formed on a silicon substrate
having a size of 3 cm.times.3 cm, in which a line and space pattern
with a height of 200 nm, a projection width of 100 nm, and a width
between projections of 100 nm was formed on the surface of the
substrate.
[0316] The sample obtained by forming the resist underlayer film on
the uneven surface of the silicon substrate was divided to perform
observation using a SEM on the cross section of one of the sample
pieces before ashing.
[0317] The ashing characteristics resulting from O.sub.2 etching
were evaluated using the other sample piece according to the
following method.
[0318] The ashing characteristics were evaluated using the same
plasma treatment device as the device used for evaluation of the
plasma etching characteristics. First, the sample was placed in a
chamber, the pressure inside the chamber was reduced to 1 Pa or
less, 30 sccm of O.sub.2 gas was introduced to the chamber, and the
pressure inside the chamber was maintained at 7 Pa. Next, a high
frequency powder of 13.56 MHz was applied thereto for plasma
discharge. The plasma etching treatment was carried out in this
manner. The plasma etching treatment was performed for 60
seconds.
[0319] After the plasma etching treatment, the ashing
characteristics were evaluated by performing observation on the
cross section of the sample after ashing using a SEM and comparing
SEM observation images before and after the plasma etching.
[Formation of Intermediate Layer]
[0320] A silicon wafer having a size of 30 mm.times.30 mm was
spin-coated with a solution containing PGMEA and cyclohexanone at a
mass ratio of 5/5, which was obtained by dissolving the cyclic
olefin polymer according to the present embodiment at a
concentration of 10% by mass, in an environment of a temperature of
23.degree. C. to 25.degree. C. and a humidity of 50% to 55% such
that the thickness thereof was set to 250 nm under conditions of
1000 rpm for 10 sec, and the coating film was baked at 200.degree.
C. for 1 minute in a nitrogen atmosphere. The coating film was
cooled to room temperature, spin-coated with a PGMEA solution, in
which 10% by mass of titanium isopropoxide was dissolved, under
conditions of 1000 rpm for 10 sec, and baked at 200.degree. C. for
1 minute in a nitrogen atmosphere to prepare a sample for
evaluation, and the cross section thereof was observed using a
TEM.
Example 1
[0321] In a 5 L autoclave equipped with a magnetic stirrer in a
nitrogen atmosphere, 320 g (2 mol) of
tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene having the
structural unit [A], 304 g (2 mol) of
4,10-dioxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one having the
structural unit [B], and 21 g (0.25 mol) of 1,5-hexadiene were
dissolved in 3.4 kg of tetrahydrofuran (hereinafter, referred to as
THF), and the solution was stirred.
[0322] As a ring opening metathesis polymerization catalyst, 612 mg
(0.8 mmol) of
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OCMe(CF.su-
b.3).sub.2).sub.2 was added thereto to cause a reaction at
60.degree. C. for 3 hours. Thereafter, 173 mg (2.4 mmol) of
n-butylaldehyde was added thereto, and the solution was cooled,
thereby obtaining 4.0 kg of a ring opening metathesis polymer
solution. In the obtained polymer, the rate of polymerization
thereof was 100%, the Mw was 5700, the ratio of Mw/Mn was 1.61, and
the molar ratio ([A]/[B]) of the structural unit [A] to the
structural unit [B] which was analyzed by .sup.1HNMR was 50/50.
[0323] Next, the cyclic olefin polymer was precipitated from the
obtained ring opening metathesis polymer solution using methanol
and dried at 80.degree. C. under reduced pressure, thereby
obtaining a white powder solid (polymer 1).
[0324] The glass transition temperature of the polymer 1 was
151.degree. C.
[0325] Further, the amount of the volatile components in the
polymer 1 was 0.0% by mass.
[0326] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 1 was 173.degree. C. (see
FIG. 1).
[0327] Next, a solution containing propylene glycol-1-monomethyl
ether-2-acetate (hereinafter, noted as PGMEA) and cyclohexanone
(hereinafter, also referred to as CH) at a mass ratio
(PGMEA/cyclohexanone) of 5/5, in which the obtained polymer 1 was
dissolved at a concentration of 10% by mass, was prepared, and a
surface of a silicon substrate A in which a line and space pattern
with a height of 200 nm, a projection width of 40 to 150 nm, and a
width between projections of 40 to 150 nm was formed was coated
with the prepared solution under conditions of 1000 rpm for 10 sec.
Thereafter, the silicon substrate A was heated at 200.degree. C.
for 3 minutes in a nitrogen atmosphere.
[0328] The refractive index (n value) of the polymer 1 measured
using an ellipsometer was 1.66 and the extinction coefficient (k
value) was 0.08.
[0329] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 1 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness (H.sub.av) of the layer of the
polymer 1 obtained by measuring ten distances between the bottoms
of recesses to the atmospheric surface and averaging the obtained
values was 300 nm, the maximum height (H.sub.max) was 301 nm, the
minimum height (H.sub.min) was 300 nm, and the flatness (.DELTA.FT)
was 0.3%.
Example 2
[0330] 2.5 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 1 except
that the monomer having the structural unit [A] was changed to
8-methoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene.
In the obtained polymer, the rate of polymerization thereof was
100%, the Mw was 6300, the ratio of Mw/Mn was 1.50, and the molar
ratio ([A]/[B]) of the structural unit [A] to the structural unit
[B] which was analyzed by .sup.1HNMR was 50/50.
[0331] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 2).
[0332] The glass transition temperature of the polymer 2 was
150.degree. C.
[0333] Further, the amount of the volatile components in the
polymer 2 was 0.0% by mass.
[0334] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 2 was 167.degree. C.
[0335] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 2 was prepared according to
the same method as that in Example 1.
[0336] The refractive index (n value) of the polymer 2 measured
using an ellipsometer was 1.66 and the extinction coefficient (k
value) was 0.04.
[0337] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 2 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 299 nm, and the flatness (.DELTA.FT) was 0.0%.
Example 3
[0338] 4.1 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 1 except
that the monomer having the structural unit [A] was changed to
8-(1-ethylcyclopentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene. In the obtained polymer, the rate of polymerization
thereof was 100%, the Mw was 7200, the ratio of Mw/Mn was 1.50, and
the molar ratio ([A]/[B]) of the structural unit [A] to the
structural unit [B] which was analyzed by .sup.1HNMR was 50/50.
[0339] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 3).
[0340] The glass transition temperature of the polymer 3 was
130.degree. C.
[0341] Further, the amount of the volatile components in the
polymer 3 was 0.0% by mass.
[0342] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 3 was 151.degree. C.
[0343] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 3 was prepared according to
the same method as that in Example 1.
[0344] The refractive index (n value) of the polymer 3 measured
using an ellipsometer was 1.68 and the extinction coefficient (k
value) was 0.02.
[0345] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 3 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 3
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
302 nm, the maximum height (H.sub.max) was 303 nm, the minimum
height (H.sub.min) was 301 nm, and the flatness (.DELTA.FT) was
0.7%.
Example 4
[0346] 4.2 kg of a ring opening metathesis polymer solution was
obtained by dissolving 437 g (2 mol) of
8-methoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene
having the structural unit [A], 121 g (0.5 mol) of
4-phenyl-4-aza-10-oxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3,5-dione
having the structural unit [B], and 21 g (0.25 mol) of
1,5-hexadiene in 3.7 kg of THF and carrying out the rest of the
process according to the same method as that in Example 1.
[0347] Next, 11.4 g (dry mass of 5.6 g) of 5% Rh carbon having a
moisture content of 50.7% was added to the obtained ring opening
metathesis polymer solution as a hydrogenation catalyst to cause a
hydrogenation reaction at 100.degree. C. and a hydrogen pressure of
5 MPa for 12 hours. In the obtained polymer, the hydrogenation
ratio thereof was 100% by mole, the Mw was 7800, the ratio of Mw/Mn
was 1.57, and the molar ratio ([A]/[B]) of the structural unit [A]
to the structural unit [B] which was analyzed by .sup.1HNMR was
80/20.
[0348] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 4).
[0349] The glass transition temperature of the polymer 4 was
172.degree. C.
[0350] Further, the amount of the volatile components in the
polymer 4 was 0.0% by mass.
[0351] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 4 was 190.degree. C.
[0352] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 4 was prepared according to
the same method as that in Example 1.
[0353] The refractive index (n value) of the polymer 4 measured
using an ellipsometer was 1.71 and the extinction coefficient (k
value) was 0.09.
[0354] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 4 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 4
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
310 nm, the maximum height (H.sub.max) was 311 nm, the minimum
height (H.sub.min) was 309 nm, and the flatness (.DELTA.FT) was
0.6%.
Example 5
[0355] 3.7 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 1 except
that the monomer having the structural unit [A] was changed to
bicycle[2.2.1]hept-2-ene. In the obtained polymer, the rate of
polymerization thereof was 100%, the Mw was 6800, the ratio of
Mw/Mn was 2.84, and the molar ratio ([A]/[B]) of the structural
unit [A] to the structural unit [B] which was analyzed by
.sup.1HNMR was 50/50.
[0356] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 5).
[0357] The glass transition temperature of the polymer 5 was
72.degree. C.
[0358] Further, the amount of the volatile components in the
polymer 5 was 0.0% by mass.
[0359] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 5 was 84.degree. C.
[0360] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 5 was prepared according to
the same method as that in Example 1.
[0361] The refractive index (n value) of the polymer 5 measured
using an ellipsometer was 1.68 and the extinction coefficient (k
value) was 0.01.
[0362] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 5 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 315 nm, and the flatness (.DELTA.FT1) was 0.0%.
Example 6
[0363] 4.0 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 1 except
that the monomer having the structural unit [A] was changed to
5-(1-ethylcyclopentyloxycarbonyl)-bicycle[2.2.1]hept-2-ene. In the
obtained polymer, the rate of polymerization thereof was 100%, the
Mw was 5600, the ratio of Mw/Mn was 1.92, and the molar ratio
([A]/[B]) of the structural unit [A] to the structural unit [B]
which was analyzed by .sup.1HNMR was 50/50.
[0364] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 6).
[0365] The glass transition temperature of the polymer 6 was
56.degree. C. Further, the amount of the volatile components in the
polymer 6 was 0.0% by mass.
[0366] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 6 was 76.degree. C.
[0367] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 6 was prepared according to
the same method as that in Example 1.
[0368] The refractive index (n value) of the polymer 6 measured
using an ellipsometer was 1.78 and the extinction coefficient (k
value) was 0.02.
[0369] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 6 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 311 nm, and the flatness (.DELTA.FT1) was 0.0%.
Example 7
[0370] 4.0 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 1 except
that the monomer having the structural unit [A] was changed to
5-(1-methylcyclohexyloxycarbonyl)-bicycle[2.2.1]hept-2-ene. In the
obtained polymer, the rate of polymerization thereof was 100%, the
Mw was 7300, the ratio of Mw/Mn was 2.17, and the molar ratio
([A]/[B]) of the structural unit [A] to the structural unit [B]
which was analyzed by .sup.1HNMR was 50/50.
[0371] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 7).
[0372] The glass transition temperature of the polymer 7 was
58.degree. C.
[0373] Further, the amount of the volatile components in the
polymer 7 was 0.0% by mass.
[0374] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 7 was 81.degree. C.
[0375] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 7 was prepared according to
the same method as that in Example 1.
[0376] The refractive index (n value) of the polymer 7 measured
using an ellipsometer was 1.78 and the extinction coefficient (k
value) was 0.01.
[0377] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 7 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 305 nm, and the flatness (.DELTA.FT1) was 0.0%.
Example 8
[0378] 4.1 kg of a ring opening metathesis polymer solution was
obtained according to the same method as in Example 3. Next, 11.4 g
(dry mass of 5.6 g) of 5% Rh carbon having a moisture content of
50.7% was added to the obtained ring opening metathesis polymer
solution as a hydrogenation catalyst to cause a hydrogenation
reaction at 100.degree. C. and a hydrogen pressure of 5 MPa for 12
hours. In the obtained polymer, the hydrogenation ratio thereof was
100% by mole, the Mw was 9600, the ratio of Mw/Mn was 2.07, and the
molar ratio ([A]/[B]) of the structural unit [A] to the structural
unit [B] which was analyzed by .sup.1HNMR was 50/50.
[0379] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 8).
[0380] The glass transition temperature of the polymer 8 was
91.degree. C.
[0381] Further, the amount of the volatile components in the
polymer 8 was 0.0% by mass.
[0382] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 8 was 112.degree. C.
[0383] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 8 was prepared according to
the same method as that in Example 1.
[0384] The refractive index (n value) of the polymer 8 measured
using an ellipsometer was 1.66 and the extinction coefficient (k
value) was 0.02.
[0385] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 8 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 8
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
310 nm, the maximum height (H.sub.max) was 311 nm, the minimum
height (H.sub.min) was 309 nm, and the flatness (.DELTA.FT) was
0.6%.
Example 9
[0386] 3.7 kg of a ring opening metathesis polymer solution was
obtained according to the same method as in Example 5. Next, 11.4 g
(dry mass of 5.6 g) of 5% Rh carbon having a moisture content of
50.7% was added to the obtained ring opening metathesis polymer
solution as a hydrogenation catalyst to cause a hydrogenation
reaction at 100.degree. C. and a hydrogen pressure of 5 MPa for 12
hours. In the obtained polymer, the hydrogenation ratio thereof was
100% by mole, the Mw was 10400, the ratio of Mw/Mn was 3.18, and
the molar ratio ([A]/[B]) of the structural unit [A] to the
structural unit [B] which was analyzed by .sup.1HNMR was 50/50.
[0387] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 9).
[0388] The glass transition temperature of the polymer 9 was
45.degree. C.
[0389] Further, the amount of the volatile components in the
polymer 9 was 0.0% by mass.
[0390] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 9 was 50.degree. C.
[0391] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 9 was prepared according to
the same method as that in Example 1.
[0392] The refractive index (n value) of the polymer 9 measured
using an ellipsometer was 1.64 and the extinction coefficient (k
value) was 0.01.
[0393] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 9 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 316 nm, and the flatness (.DELTA.FT) was 0.0%.
Example 10
[0394] 3.8 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 1 except
that 75 g (0.8 mol) of bicycle[2.2.1]hept-2-ene having the
structural unit [A] was changed to 487 g (3.2 mol) of
4,10-dioxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one having the
structural unit [B]. In the obtained polymer, the rate of
polymerization thereof was 100%, the Mw was 5900, the ratio of
Mw/Mn was 2.32, and the molar ratio ([A]/[B]) of the structural
unit [A] to the structural unit [B] which was analyzed by
.sup.1HNMR was 20/80.
[0395] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 1 to obtain a white
powder solid (polymer 10).
[0396] The glass transition temperature of the polymer 10 was
68.degree. C.
[0397] Further, the amount of the volatile components in the
polymer 10 was 0.0% by mass.
[0398] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 10 was 82.degree. C.
[0399] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 10 was prepared according to
the same method as that in Example 1.
[0400] The refractive index (n value) of the polymer 10 measured
using an ellipsometer was 1.67 and the extinction coefficient (k
value) was 0.02.
[0401] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 10 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 320 nm, and the flatness (.DELTA.FT) was 0.0%.
Example 11
[0402] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which the polymer 5 obtained
in Example 5 was dissolved at a concentration of 7% by mass, was
prepared, and a surface of a silicon substrate A in which a line
and space pattern with a height of 200 nm, a projection width of 40
to 150 nm, and a width between projections of 40 to 150 nm was
formed was coated with the prepared solution under conditions of
1000 rpm for 10 sec. Thereafter, the substrate A was heated at
200.degree. C. for 3 minutes in a nitrogen atmosphere.
[0403] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 5 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 208 nm, and the flatness (.DELTA.FT) was 0.0%.
Example 12
[0404] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which the polymer 5 obtained
in Example 5 was dissolved at a concentration of 20% by mass, was
prepared, and a surface of a silicon substrate A in which a line
and space pattern with a height of 200 nm, a projection width of 40
to 150 nm, and a width between projections of 40 to 150 nm was
formed was coated with the prepared solution under conditions of
600 rpm for 10 sec. Thereafter, the surface was heated at
200.degree. C. for 3 minutes in a nitrogen atmosphere.
[0405] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 5 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 1622 nm, and the flatness (.DELTA.FT) was 0.0%.
Example 13
[0406] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which 10% by mass of the
polymer 8 obtained in Example 8 and 0.3% by mass of
3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (EEC)
were dissolved as a crosslinking agent, was prepared, and a sample
obtained by coating the uneven surface of the silicon substrate A
with the solution was prepared according to the same method as that
in Example 1.
[0407] The refractive index (n value) measured using an
ellipsometer was 1.67 and the extinction coefficient (k value) was
0.02.
[0408] Since it was understood that the temperature at which the
polarity of the cyclic olefin polymer changes is sufficiently
higher than the temperature of the intersection between G' and G'',
the temperature of the intersection between G' and G'' of the
material for forming an underlayer film formed of the cyclic olefin
and the crosslinking agent can be regarded as the same value as
described above.
[0409] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer was uniformly embedded
without defects such as voids with respect to grooves with a narrow
line width of 40 nm (height of 200 nm) between projections.
Further, the thickness of the layer of the polymer 8 obtained by
measuring ten distances between the bottoms of recesses to the
atmospheric surface and averaging the obtained values was 313 nm,
the maximum height (H.sub.max) was 313 nm, the minimum height
(H.sub.min) was 312 nm, and the flatness (.DELTA.FT) was 0.3%.
Examples 14 to 16
[0410] Each sample obtained by coating the uneven surface of the
silicon substrate B with the polymer 5 obtained in Example 5, the
polymer 8 obtained in Example 8, and the polymer 9 obtained in
Example 9 was prepared according to the same method as that in
Example 1.
[0411] As the result of observation performed on the cross section
of the substrate B using a SEM, all of the polymer 5, the polymer
8, and the polymer 9 were uniformly embedded without defects such
as voids with respect to grooves with a.sub.1 of 900 .mu.m, b.sub.1
of 900 .mu.m, a.sub.2 of 40 nm, and b.sub.2 of 120 nm (height of
200 nm). Further, the thickness of the H.sub.1 layer of the polymer
5 obtained by measuring ten distances between the bottoms of
recesses to the atmospheric surface and averaging the obtained
values was 306 nm, the thickness of the H.sub.2 layer was 306 nm,
and the flatness (.DELTA.FT) was 0.0%.
[0412] The thickness of the H.sub.1 layer of the polymer 8 obtained
by measuring ten distances between the bottoms of recesses to the
atmospheric surface and averaging the obtained values was 301 nm,
the thickness of the H.sub.2 layer was 302 nm, and the flatness
(.DELTA.FT) was 0.3%.
[0413] Further, the thickness of the H.sub.1 layer of the polymer 9
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
298 nm, the thickness of the H.sub.2 layer was 298 nm, and the
flatness (.DELTA.FT) was 0.0%.
[Evaluation of Plasma Etching Resistance]
[0414] Each silicon wafer was coated with each solution containing
PGMEA and cyclohexanone at a mass ratio of 5/5 obtained by
dissolving 10% by mass of each of the polymers 1 to 10 synthesized
in Examples 1 to 10, and the resulting wafer was baked at
200.degree. C. for 3 minutes. Next, each sample was dry-etched for
30 seconds, 60 seconds, and 90 seconds in a CHF.sub.3 gas
atmosphere. Next, the amount of decrease in film thickness due to
the etching was calculated from the film thicknesses before and
after the etching, and the time (sec) was plotted on the horizontal
axis and the amount (nm) of the reduced film thickness was plotted
on the vertical axis. The etching rate (nm/sec) was calculated from
the inclination of the obtained graph.
[0415] The etching rate was measured using SiO.sub.2 [formed using
tetraethoxysilane (TEOS) as a raw material and baking the material
on the surface of the silicon wafer] formed on the surface of the
silicon wafer as a target substance, and the etching resistance was
evaluated based on the value [SiO.sub.2 (nm/sec)/each sample
(nm/sec)]. As the value of [SiO.sub.2 (nm/sec)/each sample
(nm/sec)] increases, this indicates that the etching resistance is
excellent.
[0416] The value of the polymer 1 was 4.5, the value of the polymer
2 was 5.0, the value of the polymer 3 was 5.0, the value of the
polymer 4 was 5.5, the value of the polymer 5 was 4.5, the value of
the polymer 6 was 5.0, the value of the polymer 7 was 5.0, the
value of the polymer 8 was 5.0, the value of the polymer 9 was 5.0,
and value of the polymer 9 was 4.5. As the result, all polymers
showed high etching resistance to SiO.sub.2.
[Evaluation of Ashing Characteristics Using O.sub.2 Etching]
[0417] Each silicon substrate, in which a line and space pattern
with a height of 200 nm, a projection width of 100 nm, and a width
between projections of 100 nm was formed on the surface of the
substrate, was coated with each solution containing PGMEA and
cyclohexanone at a mass ratio (PGMEA/cyclohexanone) of 5/5 obtained
by dissolving 10% by mass of each of the polymer 1, the polymer 2,
the polymer 3, and the polymer 4 synthesized in Example 1, Example
2, Example 3 and Example 4 respectively, and the wafer was baked at
200.degree. C. for 3 minutes in a nitrogen atmosphere. Each sample
was divided to perform SEM observation before ashing using a piece
therein, and dry etching was performed using the other piece for 60
seconds in an O.sub.2 gas atmosphere for ashing. Next, SEM
observation was performed after ashing.
[0418] Based on the comparison between SEM observation images
before and after ashing, all of the polymer 1, the polymer 2, the
polymer 3, and the polymer 4 were removed through ashing without
polymer residues on the substrate.
[0419] For comparison, the ashing characteristic evaluation was
performed according to the same method as described above using a
siloxane resin in which a substituent on Si is propoxymethacrylate.
As the result, polymer residues were found on the substrate by SEM
observation, and the polymer was not able to be removed without
polymer residues even in a case where the etching time was extended
to 180 seconds.
Comparative Example 1
[0420] A cyclohexanone solution, in which 10% by mass of a novolak
resin KA1165 (manufactured by DIC Corporation) whose temperature
showing the intersection between the storage modulus (G') curve and
the loss modulus (G'') curve calculated from the result of the
solid viscoelasticity observation was 255.degree. C. was dissolved,
was prepared, and the uneven surface of the silicon substrate was
spin-coated with the solution according to the same method as that
in Example 1 and baked at 200.degree. C. for 3 minutes.
[0421] As the result of observation performed on the cross section
using a SEM, voids were generated in recess edge portions with
respect to grooves with a narrow line width of 40 nm (height of 200
nm) between projections, and the same voids were generated in areas
with a width between projections of 100 nm. Further, the thickness
of the layer of the polymer 1 obtained by measuring ten distances
between the bottoms of recesses to the atmospheric surface and
averaging the obtained values was 300 nm, the maximum height
(H.sub.max) was 317 nm, the minimum height (H.sub.min) was 285 nm,
and the flatness (.DELTA.FT) was 10.7%.
Comparative Example 2
[0422] A cyclohexanone solution containing 10% by mass of methyl
methacrylate was prepared. In the cyclohexanone solution, 2% by
mass with respect to the methyl methacrylate of
2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one as a
photopolymerization initiator was dissolved, and a solution was
obtained.
[0423] Next, a sample obtained by coating the uneven surface of the
silicon substrate B with the solution was prepared according to the
same method as that in Example 1.
[0424] Next, the coating film was cured by being irradiated with UV
rays at an irradiation dose of 1000 mJ/cm.sup.2.
[0425] Next, as the result of observation performed on the cross
section using a SEM, voids were generated in areas with a width
between projections of 900 .mu.m with respect to grooves with
a.sub.1 of 900 .mu.m, b.sub.1 of 900 .mu.m, a.sub.2 of 40 nm, and
b.sub.2 of 120 nm (height of 200 nm), and the same voids were
generated in areas with a width between projections of 40 nm.
Further, the thickness of the H.sub.1 layer obtained by measuring
ten distances between the bottoms of recesses to the atmospheric
surface and averaging the obtained values was 250 nm, the thickness
of the H.sub.2 layer was 264 nm, and the flatness (.DELTA.FT) was
11.2%. Further, the atmospheric surface was distorted.
[0426] The above-described results are listed in Table 1 and Table
2.
TABLE-US-00001 TABLE 1 Example 1 Example 2 Example 3 Example 4
Example 5 Example 6 Example 7 Example 8 Example 9 Polymer Polymer 1
Polymer 2 Polymer 3 Polymer 4 Polymer 5 Polymer 6 Polymer 7 Polymer
8 Polymer 9 Mw 5700 6300 7200 7800 6800 5600 7300 9600 10400 Mw/Mn
1.61 1.50 1.50 1.57 2.84 1.92 2.17 2.07 3.18 A structure/ 50/50
50/50 50/50 80/20 50/50 50/50 50/50 50/50 50/50 B structure Tg
151.degree. C. 150.degree. C. 130.degree. C. 172.degree. C.
72.degree. C. 56.degree. C. 58.degree. C. 91.degree. C. 45.degree.
C. Amount of 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% volatile
component to be generated Intersection 173.degree. C. 167.degree.
C. 151.degree. C. 190.degree. C. 84.degree. C. 76.degree. C.
81.degree. C. 112.degree. C. 50.degree. C. between G' and G''
Solution for PGMEA/CH PGMEA/CH PGMEA/CH PGMEA/CH PGMEA/CH PGMEA/CH
PGMEA/CH PGMEA/CH PGMEA/CH measurement of polymer of polymer of
polymer of polymer of polymer of polymer of polymer of polymer of
polymer 10 (%) = 10 (%) = 10 (%) = 10 (%) = 10 (%) = 10 (%) = 10
(%) = 10 (%) = 10 (%) = 50/50 50/50 50/50 50/50 50/50 50/50 50/50
50/50 50/50 Refractive 1.66 1.66 1.68 1.71 1.68 1.78 1.78 1.66 1.64
index (n value) Extinction 0.08 0.04 0.02 0.09 0.01 0.02 0.01 0.02
0.01 coefficient (k value) Substrate A A A A A A A A A Embedding
Uniform Uniform Uniform Uniform Uniform Uniform Uniform Uniform
Uniform property Average value 300 nm 299 nm 302 nm 310 nm 315 nm
311 nm 305 nm 310 nm 316 nm (Hav) of thicknesses of resist
underlayer film applied to substrate A Flatness (.DELTA.FT) 0.3%
0.0% 0.7% 0.6% 0.0% 0.0% 0.0% 0.6% 0.0%
TABLE-US-00002 TABLE 2 Comparative Comparative Example 10 Example
11 Example 12 Example 13 Example 14 Example 15 Example 16 Example 1
Example 2 Polymer Polymer 10 Polymer 5 Polymer 5 10 parts by
Polymer 5 Polymer 8 Polymer 9 Novolak PMMA mass of resin
(photocuring) polymer 8 0.3 parts by mass of crosslinking agent
(EEC) Mw 5900 -- -- -- -- -- -- -- -- Mw/Mn 2.32 -- -- -- -- -- --
-- -- A structure/ 20/80 -- -- -- -- -- -- -- -- B structure Tg
68.degree. C. -- -- -- -- -- -- -- -- Amount of 0.01 -- -- -- -- --
-- -- -- volatile component to be generated Intersection 82.degree.
C. -- -- -- -- -- -- 255.degree. C. between G' and G'' Solution for
PGMEA/CH -- -- PGMEA/CH -- -- -- Novolak Methyl measurement of
polymer of polymer resin/CH = methacrylate/ 10 (%) = 10 (%) = 10/90
CH = 10/90 50/50 50/50 Refractive 1.67 -- -- 1.67 -- -- -- -- --
index (n value) Extinction 0.02 -- -- 0.02 -- -- -- -- --
coefficient (k value) Substrate A A A A B B B A B Embedding Uniform
Uniform Uniform Uniform Uniform Uniform Uniform Non-uniform
Non-uniform property Average value 320 nm 208 1622 313 nm -- -- --
300 nm -- (Hav) of thicknesses of resist underlayer film applied to
substrate A Average value -- -- -- -- 306 nm 302 nm 298 nm -- 250
nm (H3) of thicknesses of resist underlayer film applied to
substrate B Flatness (.DELTA.FT) 0.0% 0.0% 0.0% 0.3% 0.0% 0.3% 0.0%
10.7% 11.2%
Example 17
[0427] In a 5 L autoclave equipped with a magnetic stirrer in a
nitrogen atmosphere, 320 g (2 mol) of
tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene having the
structural unit [A], 304 g (2 mol) of
4,10-dioxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one having the
structural unit [B], and 21 g (0.25 mol) of 1,5-hexadiene were
dissolved in 3.4 kg of tetrahydrofuran (hereinafter, referred to as
THF), and the solution was stirred.
[0428] As a ring opening metathesis polymerization catalyst, 612 mg
(0.8 mmol) of
Mo(N-2,6-Pr.sup.i.sub.2C.sub.6H.sub.3)(CHCMe.sub.2Ph)(OCMe(CF.su-
b.3).sub.2).sub.2 was added thereto to cause a reaction at
60.degree. C. for 3 hours. Thereafter, 173 mg (2.4 mmol) of
n-butylaldehyde was added thereto, and the solution was cooled,
thereby obtaining 4.0 kg of a ring opening metathesis polymer
solution. In the obtained polymer, the rate of polymerization
thereof was 100%, the Mw was 5700, the ratio of Mw/Mn was 1.61, and
the molar ratio ([A]/[B]) of the structural unit [A] to the
structural unit [B] which was analyzed by .sup.1HNMR was 50/50.
[0429] Next, the cyclic olefin polymer was precipitated from the
obtained ring opening metathesis polymer solution using methanol
and dried at 80.degree. C. under reduced pressure, thereby
obtaining a white powder solid (polymer 14).
[0430] The glass transition temperature of the polymer 14 was
151.degree. C.
[0431] Next, a solution containing propylene glycol-1-monomethyl
ether-2-acetate (hereinafter, noted as PGMEA) and cyclohexanone
(hereinafter, also referred to as CH) at a mass ratio
(PGMEA/cyclohexanone) of 5/5, in which the obtained polymer 14 was
dissolved at a concentration of 10% by mass was prepared, and a
surface of a silicon substrate A in which a line and space pattern
with a height of 200 nm, a projection width of 40 to 150 nm, and a
width between projections of 40 to 150 nm was formed was coated
with the prepared solution under conditions of 1000 rpm for 10 sec.
Thereafter, the silicon substrate A was heated at 200.degree. C.
for 3 minutes in a nitrogen atmosphere.
[0432] The refractive index (n value) of the polymer 14 measured
using an ellipsometer was 1.66 and the extinction coefficient (k
value) was 0.08.
[0433] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 14 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 14
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
300 nm, the maximum height (H.sub.max) was 301 nm, the minimum
height (H.sub.min) was 300 nm, and the flatness (.DELTA.FT) was
0.3%.
[0434] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which 10% by mass of the
obtained polymer 14 was dissolved was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0435] Next, the residual film rate of the polymer 14 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 88%. Further, the residual
film rate of the polymer 14 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 96%.
[0436] Reference information: The residual film rate thereof was 9%
in a case where the film in the intermediate stage was immersed in
PGMEA without being treated at 200.degree. C.
[0437] Further, the residual film rate of the polymer 14 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 99%. Further, the residual
film rate of the polymer 14 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 99%.
[0438] Reference information: The residual film rate thereof was
2.4% in a case where the film in the intermediate stage was
immersed in PGME without being treated at 200.degree. C.
[0439] Further, the residual film rate of the polymer 14 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 94%.
Further, the residual film rate of the polymer 14 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 98%.
[0440] Reference information: The residual film rate thereof was
3.7% in a case where the film in the intermediate stage was
immersed in PGME/PGMEA (7/3) without being treated at 200.degree.
C.
Example 18
[0441] 2.5 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 17 except
that the monomer having the structural unit [A] was changed to
8-methoxycarbonyl-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene.
In the obtained polymer, the rate of polymerization thereof was
100%, the Mw was 6300, the ratio of Mw/Mn was 1.50, and the molar
ratio ([A]/[B]) of the structural unit [A] to the structural unit
[B] which was analyzed by .sup.1HNMR was 50/50.
[0442] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 15).
[0443] The glass transition temperature of the polymer 15 was
150.degree. C.
[0444] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 15 was prepared according to
the same method as that in Example 17.
[0445] The refractive index (n value) of the polymer 15 measured
using an ellipsometer was 1.66 and the extinction coefficient (k
value) was 0.04.
[0446] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 15 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 299 nm, and the flatness (.DELTA.FT) was 0.0%.
[0447] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which 10% by mass of the
obtained polymer 15 was dissolved was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0448] Next, the residual film rate of the polymer 15 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 58%. Further, the residual
film rate of the polymer 15 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 92%.
[0449] Reference information: The residual film rate thereof was
0.3% in a case where the film in the intermediate stage was
immersed in PGMEA as it was.
[0450] Further, the residual film rate of the polymer 15 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 60%. Further, the residual
film rate of the polymer 15 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 94%.
[0451] Reference information: The residual film rate thereof was
0.3% in a case where the film in the intermediate stage was
immersed in PGME without being treated at 200.degree. C.
[0452] Further, the residual film rate of the polymer 15 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 60%.
Further, the residual film rate of the polymer 15 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 93%.
[0453] Reference information: The residual film rate thereof was
0.3% in a case where the film in the intermediate stage was
immersed in PGME/PGMEA (7/3) without being treated at 200.degree.
C.
Example 19
[0454] 4.1 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 17 except
that the monomer having the structural unit [A] was changed to
8-(1-ethylcyclopentyloxycarbonyl)-tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]--
3-dodecene. In the obtained polymer, the rate of polymerization
thereof was 100%, the Mw was 7200, the ratio of Mw/Mn was 1.50, and
the molar ratio ([A]/[B]) of the structural unit [A] to the
structural unit [B] which was analyzed by .sup.1HNMR was 50/50.
[0455] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 16).
[0456] The glass transition temperature of the polymer 16 was
130.degree. C.
[0457] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 16 was prepared according to
the same method as that in Example 17.
[0458] The refractive index (n value) of the polymer 16 measured
using an ellipsometer was 1.68 and the extinction coefficient (k
value) was 0.02.
[0459] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 16 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 16
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
302 nm, the maximum height (H.sub.max) was 303 nm, the minimum
height (H.sub.min) was 301 nm, and the flatness (.DELTA.FT) was
0.7%.
[0460] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which 10% by mass of the
obtained polymer 16 was dissolved was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0461] Next, the residual film rate of the polymer 16 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 97%. Further, the residual
film rate of the polymer 16 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 98%.
[0462] Reference information: The residual film rate thereof was
0.3% in a case where the film in the intermediate stage was
immersed in PGMEA as it was.
[0463] Further, the residual film rate of the polymer 16 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 81%. Further, the residual
film rate of the polymer 16 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 95%.
[0464] Reference information: The residual film rate thereof was
0.3% in a case where the film in the intermediate stage was
immersed in PGME without being treated at 200.degree. C.
[0465] Further, the residual film rate of the polymer 16 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 88%.
Further, the residual film rate of the polymer 16 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 96%.
[0466] Reference information: The residual film rate thereof was
0.3% in a case where the film in the intermediate stage was
immersed in PGME/PGMEA (7/3) without being treated at 200.degree.
C.
Example 20
[0467] 4.1 kg of a ring opening metathesis polymer solution was
obtained according to the same method as in Example 19. Next, 11.4
g (dry mass of 5.6 g) of 5% Rh carbon having a moisture content of
50.7% was added to the obtained ring opening metathesis polymer
solution as a hydrogenation catalyst to cause a hydrogenation
reaction at 100.degree. C. and a hydrogen pressure of 5 MPa for 12.
In the obtained polymer, the hydrogenation ratio thereof was 100%
by mole, the Mw was 7800, the ratio of Mw/Mn was 1.57, and the
molar ratio ([A]/[B]) of the structural unit [A] to the structural
unit [B] which was analyzed by .sup.1HNMR was 50/50.
[0468] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 17).
[0469] The glass transition temperature of the polymer 17 was
91.degree. C.
[0470] Further, the amount of the volatile components in the
polymer 17 was 0.0% by mass.
[0471] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 17 was 112.degree. C.
[0472] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 17 was prepared according to
the same method as that in Example 17.
[0473] The refractive index (n value) of the polymer 17 measured
using an ellipsometer was 1.66 and the extinction coefficient (k
value) was 0.02.
[0474] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 17 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 17
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
310 nm, the maximum height (H.sub.max) was 311 nm, the minimum
height (H.sub.min) was 309 nm, and the flatness (.DELTA.FT) was
0.6%.
[0475] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which 10% by mass of the
obtained polymer 17 was dissolved was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0476] Next, the residual film rate of the polymer 17 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 75%. Further, the residual
film rate of the polymer 17 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 93%.
[0477] Reference information: The residual film rate thereof was
0.5% in a case where the film in the intermediate stage was
immersed in PGMEA as it was.
[0478] Further, the residual film rate of the polymer 17 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 66%. Further, the residual
film rate of the polymer 17 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 92%.
[0479] Reference information: The residual film rate thereof was
0.2% in a case where the film in the intermediate stage was
immersed in PGME without being treated at 200.degree. C.
[0480] Further, the residual film rate of the polymer 17 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 69%.
Further, the residual film rate of the polymer 17 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 92%.
[0481] Reference information: The residual film rate thereof was
0.3% in a case where the film in the intermediate stage was
immersed in PGME/PGMEA (7/3) without being treated at 200.degree.
C.
Example 21
[0482] 3.7 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 17 except
that the monomer having the structural unit [A] was changed to
bicycle[2.2.1]hept-2-ene. In the obtained polymer, the rate of
polymerization thereof was 100%, the Mw was 6800, the ratio of
Mw/Mn was 2.84, and the molar ratio ([A]/[B]) of the structural
unit [A] to the structural unit [B] which was analyzed by
.sup.1HNMR was 50/50.
[0483] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 18).
[0484] The glass transition temperature of the polymer 18 was
72.degree. C.
[0485] Further, the amount of the volatile components in the
polymer 18 was 0.0% by mass.
[0486] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 18 was 84.degree. C.
[0487] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 18 was prepared according to
the same method as that in Example 17.
[0488] The refractive index (n value) of the polymer 18 measured
using an ellipsometer was 1.68 and the extinction coefficient (k
value) was 0.01.
[0489] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 18 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 18
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
262 nm, the maximum height (H.sub.max) was 262 nm, the minimum
height (H.sub.min) was 262 nm, and the flatness (.DELTA.FT) was
0.0%.
[0490] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5 in which 10% by mass of the
obtained polymer 18 was dissolved was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0491] Next, the residual film rate of the polymer 18 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 99%. Further, the residual
film rate of the polymer 18 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 99%.
[0492] Reference information: The residual film rate thereof was
30% in a case where the film in the intermediate stage was immersed
in PGMEA as it was.
[0493] Further, the residual film rate of the polymer 18 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 96%. Further, the residual
film rate of the polymer 18 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 99%.
[0494] Reference information: The residual film rate thereof was
1.8% in a case where the film in the intermediate stage was
immersed in PGME without being treated at 200.degree. C.
[0495] Further, the residual film rate of the polymer 18 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 71%.
Further, the residual film rate of the polymer 18 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 99%.
[0496] Reference information: The residual film rate thereof was
9.4% in a case where the film in the intermediate stage was
immersed in PGME/PGMEA (7/3) without being treated at 200.degree.
C.
Example 22
[0497] 4.0 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 17 except
that the monomer having the structural unit [A] was changed to
5-(1-ethylcyclopentyloxycarbonyl)-bicycle[2.2.1]hept-2-ene. In the
obtained polymer, the rate of polymerization thereof was 100%, the
Mw was 5600, the ratio of Mw/Mn was 1.92, and the molar ratio
([A]/[B]) of the structural unit [A] to the structural unit [B]
which was analyzed by .sup.1HNMR was 50/50.
[0498] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 19).
[0499] The glass transition temperature of the polymer 19 was
56.degree. C.
[0500] Further, the amount of the volatile components in the
polymer 19 was 0.0% by mass.
[0501] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 19 was 76.degree. C.
[0502] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 19 was prepared according to
the same method as that in Example 17.
[0503] The refractive index (n value) of the polymer 19 measured
using an ellipsometer was 1.78 and the extinction coefficient (k
value) was 0.02.
[0504] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 19 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 19
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
264 nm, the maximum height (H.sub.max) was 266 nm, the minimum
height (H.sub.min) was 264 nm, and the flatness (.DELTA.FT) was
0.8%.
[0505] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5 in which 10% by mass of the
obtained polymer 19 was dissolved was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0506] Next, the residual film rate of the polymer 19 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 99%. Further, the residual
film rate of the polymer 19 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 100%.
[0507] Reference information: The residual film rate thereof was
3.0% in a case where the film in the intermediate stage was
immersed in PGMEA as it was.
[0508] Further, the residual film rate of the polymer 19 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 71%. Further, the residual
film rate of the polymer 19 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 95%.
[0509] Reference information: The residual film rate thereof was
2.2% in a case where the film in the intermediate stage was
immersed in PGME without being treated at 200.degree. C.
[0510] Further, the residual film rate of the polymer 19 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 76%.
Further, the residual film rate of the polymer 19 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 95%.
[0511] Reference information: The residual film rate thereof was
2.5% in a case where the film in the intermediate stage was
immersed in PGME/PGMEA (7/3) without being treated at 200.degree.
C.
Example 23
[0512] 4.0 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 17 except
that the monomer having the structural unit [A] was changed to
5-(1-methylcyclohexyloxycarbonyl)-bicycle[2.2.1]hept-2-ene. In the
obtained polymer, the rate of polymerization thereof was 100%, the
Mw was 7300, the ratio of Mw/Mn was 2.17, and the molar ratio
([A]/[B]) of the structural unit [A] to the structural unit [B]
which was analyzed by .sup.1HNMR was 50/50.
[0513] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 20).
[0514] The glass transition temperature of the polymer 20 was
58.degree. C.
[0515] Further, the amount of the volatile components in the
polymer 20 was 0.0% by mass.
[0516] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 20 was 81.degree. C.
[0517] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 20 was prepared according to
the same method as that in Example 17.
[0518] The refractive index (n value) of the polymer 20 measured
using an ellipsometer was 1.78 and the extinction coefficient (k
value) was 0.01.
[0519] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 20 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 20
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
263 nm, the maximum height (H.sub.max) was 264 nm, the minimum
height (H.sub.min) was 262 nm, and the flatness (.DELTA.FT) was
0.8%.
[0520] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5 in which 10% by mass of the
obtained polymer 20 was dissolved was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0521] Next, the residual film rate of the polymer 20 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 100%. Further, the residual
film rate of the polymer 20 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 100%.
[0522] Reference information: The residual film rate thereof was
10% in a case where the film in the intermediate stage was immersed
in PGMEA as it was.
[0523] Further, the residual film rate of the polymer 20 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 100%. Further, the residual
film rate of the polymer 20 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 100%.
[0524] Reference information: The residual film rate thereof was
10% in a case where the film in the intermediate stage was immersed
in PGME without being treated at 200.degree. C.
[0525] Further, the residual film rate of the polymer 20 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 98%.
Further, the residual film rate of the polymer 20 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 100%.
[0526] Reference information: The residual film rate thereof was
10% in a case where the film in the intermediate stage was immersed
in PGME/PGMEA (7/3) without being treated at 200.degree. C.
Example 24
[0527] 3.7 kg of a ring opening metathesis polymer solution was
obtained according to the same method as in Example 21. Next, 11.4
g (dry mass of 5.6 g) of 5% Rh carbon having a moisture content of
50.7% was added to the obtained ring opening metathesis polymer
solution as a hydrogenation catalyst to cause a hydrogenation
reaction at 100.degree. C. and a hydrogen pressure of 5 MPa for 12
hours. In the obtained polymer, the hydrogenation ratio thereof was
100% by mole, the Mw was 10400, the ratio of Mw/Mn was 3.18, and
the molar ratio ([A]/[B]) of the structural unit [A] to the
structural unit [B] which was analyzed by .sup.1HNMR was 50/50.
[0528] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 21).
[0529] The glass transition temperature of the polymer 21 was
45.degree. C.
[0530] Further, the amount of the volatile components in the
polymer 21 was 0.0% by mass.
[0531] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 21 was 50.degree. C.
[0532] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 21 was prepared according to
the same method as that in Example 17.
[0533] The refractive index (n value) of the polymer 21 measured
using an ellipsometer was 1.66 and the extinction coefficient (k
value) was 0.02.
[0534] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 21 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, the thickness of the layer of the polymer 21
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
273 nm, the maximum height (H.sub.max) was 273 nm, the minimum
height (H.sub.min) was 273 nm, and the flatness (.DELTA.FT) was
0.0%.
[0535] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5 in which 10% by mass of the
obtained polymer 21 was dissolved was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0536] Next, the residual film rate of the polymer 21 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 79%. Further, the residual
film rate of the polymer 21 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 97%.
[0537] Reference information: The residual film rate thereof was
0.8% in a case where the film in the intermediate stage was
immersed in PGMEA as it was.
[0538] Further, the residual film rate of the polymer 21 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 74%. Further, the residual
film rate of the polymer 21 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 93%.
[0539] Reference information: The residual film rate thereof was
6.2% in a case where the film in the intermediate stage was
immersed in PGME without being treated at 200.degree. C.
[0540] Further, the residual film rate of the polymer 21 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 76%.
Further, the residual film rate of the polymer 21 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 94%.
[0541] Reference information: The residual film rate thereof was
6.0% in a case where the film in the intermediate stage was
immersed in PGME/PGMEA (7/3) without being treated at 200.degree.
C.
Example 25
[0542] 3.8 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 17 except
that 75 g (0.8 mol) of bicycle[2.2.1]hept-2-ene having the
structural unit [A] was changed to 487 g (3.2 mol) of
4,10-dioxy-tricyclo[5.2.1.0.sup.2,6]-8-decene-3-one having the
structural unit [B]. In the obtained polymer, the rate of
polymerization thereof was 100%, the Mw was 5900, the ratio of
Mw/Mn was 2.32, and the molar ratio ([A]/[B]) of the structural
unit [A] to the structural unit [B] which was analyzed by
.sup.1HNMR was 20/80. Next, the cyclic olefin polymer was
precipitated and dried according to the same method as that in
Example 17 to obtain a white powder solid (polymer 22).
[0543] The glass transition temperature of the polymer 22 was
68.degree. C.
[0544] Further, the amount of the volatile components in the
polymer 22 was 0.0% by mass.
[0545] In addition, the temperature showing the intersection
between the storage modulus (G') curve and the loss modulus (G'')
curve which were calculated from the results obtained by measuring
the solid viscoelasticity of the polymer 22 was 82.degree. C.
[0546] Next, a sample obtained by coating the uneven surface of the
silicon substrate A with the polymer 22 was prepared according to
the same method as that in Example 17.
[0547] The refractive index (n value) of the polymer 22 measured
using an ellipsometer was 1.67 and the extinction coefficient (k
value) was 0.02.
[0548] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer 22 was uniformly
embedded without defects such as voids with respect to grooves with
a narrow line width of 40 nm (height of 200 nm) between
projections. Further, all measured values obtained by measuring ten
distances between the bottoms of recesses to the atmospheric
surface were 260 nm, and the flatness (.DELTA.FT) was 0.0%. A
solution containing PGMEA and cyclohexanone at a mass ratio
(PGMEA/cyclohexanone) of 5/5 in which 10% by mass of the obtained
polymer 22 was dissolved was prepared, and a 4 inch silicon wafer
was spin-coated with the obtained solution under conditions of 1000
rpm for 10 sec. Next, the resulting sample was baked at 80.degree.
C. for 5 hours under reduced pressure (intermediate stage).
[0549] Next, the residual film rate of the polymer 22 with respect
to PGMEA obtained by heating the film at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 99%. Further, the residual
film rate of the polymer 20 with respect to PGMEA obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 100%.
[0550] Reference information: The residual film rate thereof was
31% in a case where the film in the intermediate stage was immersed
in PGMEA as it was.
[0551] Further, the residual film rate of the polymer 22 with
respect to PGME obtained by heating the film at 200.degree. C. for
10 minutes in a nitrogen atmosphere was 98%. Further, the residual
film rate of the polymer 22 with respect to PGME obtained by
heating the film at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 100%.
[0552] Reference information: The residual film rate thereof was
26% in a case where the film in the intermediate stage was immersed
in PGME without being treated at 200.degree. C.
[0553] Further, the residual film rate of the polymer 22 with
respect to PGME/PGMEA (7/3) obtained by heating the film at
200.degree. C. for 10 minutes in a nitrogen atmosphere was 97%.
Further, the residual film rate of the polymer 22 with respect to
PGME/PGMEA (7/3) obtained by heating the film at 200.degree. C. for
30 minutes in a nitrogen atmosphere was 100%.
[0554] Reference information: The residual film rate thereof was
27% in a case where the film in the intermediate stage was immersed
in PGME/PGMEA (7/3) without being treated at 200.degree. C.
Example 26
[0555] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which 10% by mass of the
polymer 17 obtained in Example 20 and 0.3% by mass of
3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (EEC)
were dissolved as a crosslinking agent was prepared, and a sample
obtained by coating the uneven surface of the silicon substrate A
with the solution was prepared according to the same method as that
in Example 17.
[0556] The refractive index (n value) measured using an
ellipsometer was 1.67 and the extinction coefficient (k value) was
0.02. Since it was understood that the temperature at which the
polarity of the cyclic olefin polymer changes is sufficiently
higher than 112.degree. C. which is the temperature of the
intersection between G' and G'', the temperature of the
intersection between G' and G'' of the material for forming an
underlayer film formed of the cyclic olefin and the crosslinking
agent can be regarded as the same value as described above.
[0557] As the result of observation performed on the cross section
of the substrate A using a SEM, the polymer was uniformly embedded
without defects such as voids with respect to grooves with a narrow
line width of 40 nm (height of 200 nm) between projections.
[0558] Further, the thickness of the layer of the polymer 8
obtained by measuring ten distances between the bottoms of recesses
to the atmospheric surface and averaging the obtained values was
313 nm, the maximum height (H.sub.max) was 313 nm, the minimum
height (H.sub.min) was 312 nm, and the flatness (.DELTA.FT) was
0.3%.
[0559] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5, in which 10% by mass of the
obtained polymer 17 and 0.3% by mass of
3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (EEC)
were dissolved as a crosslinking agent was prepared, and a 4 inch
silicon wafer was spin-coated with the obtained solution under
conditions of 1000 rpm for 10 sec. Next, the resulting sample was
baked at 80.degree. C. for 5 hours under reduced pressure
(intermediate stage).
[0560] Next, the residual film rate of the film with respect to
PGMEA obtained by being heated at 200.degree. C. for 10 minutes in
a nitrogen atmosphere was 95%. Next, the residual film rate of the
film with respect to PGMEA obtained by being heated at 200.degree.
C. for 30 minutes in a nitrogen atmosphere was 100%.
[0561] Reference information: The residual film rate thereof was
0.5% in a case where the film in the intermediate stage was
immersed in PGMEA as it was.
[0562] Further, the residual film rate of the film with respect to
PGME obtained by being heated at 200.degree. C. for 10 minutes in a
nitrogen atmosphere was 94%. Further, the residual film rate of the
film with respect to PGME obtained by being heated at 200.degree.
C. for 30 minutes in a nitrogen atmosphere was 100%.
[0563] Reference information: The residual film rate thereof was
0.2% in a case where the film in the intermediate stage was
immersed in PGME without being treated at 200.degree. C.
[0564] Further, the residual film rate of the film obtained by
being heated at 200.degree. C. for 10 minutes in a nitrogen
atmosphere to PGME/PGMEA (7/3) was 94%. Further, the residual film
rate of the film with respect to PGME/PGMEA (7/3) obtained by being
heated at 200.degree. C. for 30 minutes in a nitrogen atmosphere
was 100%.
[0565] Reference information: The residual film rate thereof was
0.3% in a case where the film in the intermediate stage was
immersed in PGME/PGMEA (7/3) without being treated at 200.degree.
C.
Comparative Example 3
[0566] A solution in which 10% by mass of PGMEA was dissolved was
prepared in the same manner as in Example 17 except that
polyhydroxystyrene (hereinafter, noted as PHS, manufactured by
Polysciences, Inc., Mw=5300, Mw/Mn=1.48) was used, and a 4 inch
silicon wafer was spin-coated with this solution and baked at
200.degree. C. for 10 minutes.
[0567] As the result of evaluation of the residual film rate in the
same manner as in Example 17, the residual film rate of PHS with
respect to PGMEA obtained by performing only drying at 80.degree.
C. for 5 hours under reduced pressure was 0.2%. The residual film
rate of PHS obtained by performing heating at 200.degree. C. for 10
minutes in a nitrogen atmosphere was 0.4%. Further, the residual
film rate of PHS obtained by performing heating at 200.degree. C.
for 30 minutes in a nitrogen atmosphere was 0.6%, and the mode of
being insoluble in PGMEA during both heating times was not
observed.
[0568] Further, the residual film rate of PHS with respect to PGME
obtained by performing only drying at 80.degree. C. for 5 hours
under reduced pressure was 0.1%. The residual film rate of PHS
obtained by performing heating at 200.degree. C. for 10 minutes in
a nitrogen atmosphere was 0.4%. Further, the residual film rate of
PHS obtained by performing heating at 200.degree. C. for 30 minutes
in a nitrogen atmosphere was 0.5%, and the mode of being insoluble
in PGME during both heating times was not observed. Further, the
residual film rate of PHS with respect to PGME/PGMEA (7/3) obtained
by performing only drying at 80.degree. C. for 5 hours under
reduced pressure was 0.1%. The residual film rate of PHS obtained
by performing heating at 200.degree. C. for 10 minutes in a
nitrogen atmosphere was 0.4%. Further, the residual film rate of
PHS obtained by performing heating at 200.degree. C. for 30 minutes
in a nitrogen atmosphere was 0.5%, and the mode of being insoluble
in PGME/PGMEA (7/3) during both heating times was not observed.
Comparative Example 4
[0569] 4.1 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 17 except
that the monomer having the structural unit [A] was changed to
5,5,6-trifluoro-6-(trifluoromethyl)-bicyclo 8-[2.2.1]hept-2-ene),
and the monomer having the structural unit [B] was used.
[0570] Next, 51.7 g (dry mass of 24.8 g) of 5% Pd carbon having a
moisture content of 52.0% was added to the obtained ring opening
metathesis polymer solution as a hydrogenation catalyst to cause a
hydrogenation reaction at 130.degree. C. and a hydrogen pressure of
8.5 MPa for 20 hours. In the obtained polymer, the hydrogenation
ratio thereof was 100% by mole, the Mw was 9300, and the ratio of
Mw/Mn was 1.76.
[0571] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 23).
[0572] As the result of evaluation of the residual film rate in the
same manner as in Example 17, the residual film rate of the polymer
23 with respect to PGMEA obtained by performing only drying at
80.degree. C. for 5 hours under reduced pressure was 0.3%. The
residual film rate of the polymer 23 obtained by performing heating
at 200.degree. C. for 10 minutes in a nitrogen atmosphere was 0.5%.
Further, the residual film rate of the polymer 23 obtained by
performing heating at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 0.8%, and the mode of being insoluble in PGMEA
during both heating times was not observed.
[0573] Further, the residual film rate of the polymer 23 with
respect to PGME obtained by performing only drying at 80.degree. C.
for 5 hours under reduced pressure was 25%. The residual film rate
of the polymer 23 obtained by performing heating at 200.degree. C.
for 10 minutes in a nitrogen atmosphere was 27%. Further, the
residual film rate of the polymer 23 obtained by performing heating
at 200.degree. C. for 30 minutes in a nitrogen atmosphere was 28%,
and the mode of being insoluble in PGME during both heating times
was not observed. Further, the residual film rate of the polymer 23
with respect to PGME/PGMEA (7/3) obtained by performing only drying
at 80.degree. C. for 5 hours under reduced pressure was 33%. The
residual film rate of the polymer 23 obtained by performing heating
at 200.degree. C. for 10 minutes in a nitrogen atmosphere was 35%.
Further, the residual film rate of the polymer 23 obtained by
performing heating at 200.degree. C. for 30 minutes in a nitrogen
atmosphere was 35%, and the mode of being insoluble in PGME/PGMEA
(7/3) during both heating times was not observed.
Comparative Example 5
[0574] 4.2 kg of a ring opening metathesis polymer solution was
obtained according to the same method as that in Example 17 except
that the monomer having the structural unit [A] was changed to
tetracyclo[4.4.0.1.sup.2,5.1.sup.7,10]-3-dodecene and the monomer
having the structural unit [B] was not used. In the obtained
polymer, the hydrogenation ratio thereof was 100% by mole, the Mw
was 6800, and the ratio of Mw/Mn was 1.55.
[0575] Next, the cyclic olefin polymer was precipitated and dried
according to the same method as that in Example 17 to obtain a
white powder solid (polymer 24).
[0576] The residual film rate of the polymer 24 which had only been
dried at 80.degree. C. for 5 hours under reduced pressure was not
able to be measured with an ellipsometer because the film was
whitened due to a phenomenon in which the film was swollen at the
time of being immersed in PGMEA. The residual film rate of the
polymer 24 obtained by heating the film at 200.degree. C. for 10
minutes or 30 minutes in a nitrogen atmosphere was not able to be
measured with an ellipsometer due to the similar whitening. The
residual film rate with respect to PGME and PGME/PGMEA (7/3) was
not able to be measured with an ellipsometer because the film was
whitened due to a phenomenon in which the film was swollen at the
time of being immersed similar to PGMEA.
[0577] The results of the residual film rates described above are
listed in Table 3 and Table 4.
TABLE-US-00003 TABLE 3 80.degree. C. for 5 hours under 200.degree.
C. for 10 minutes in 200.degree. C. for 30 minutes in reduced
pressure nitrogen atmosphere nitrogen atmosphere Residual Residual
Residual .alpha. .beta. film rate .alpha. .beta. film rate .alpha.
.beta. film rate Solvent (nm) (nm) (%)* (nm) (nm) (%)* (nm) (nm)
(%)* Example 17 Polymer 14 PGMEA 436 49 9 387 351 88 377 366 96 436
35 387 330 375 357 442 39 386 340 374 357 PGME 440 11 2.4 389 386
99 372 369 99 437 10 386 381 368 363 438 11 385 381 374 371 PGME/
432 14 3.7 388 363 94 370 365 98 PGMEA = 433 16 383 360 369 360 7/3
439 18 386 363 375 366 Example 18 Polymer 15 PGMEA 367 1.1 0.3 331
191 58 315 296 92 369 1.2 331 189 322 290 368 1.5 326 193 318 293
PGME 366 1.2 0.3 333 197 60 318 298 94 366 1.1 325 196 312 292 363
1.2 325 193 320 299 PGME/ 369 1.0 0.3 329 198 60 317 295 93 PGMEA =
366 1.1 326 195 315 291 7/3 365 1.1 331 196 322 298 Example 19
Polymer 16 PGMEA 356 3.0 0.3 246 239 97 240 235 98 357 0.2 245 235
241 234 345 0.2 247 242 239 233 PGME 348 1.0 0.3 244 196 81 244 233
95 352 1.1 250 203 240 225 355 1.1 249 200 242 229 PGME/ 355 0.8
0.3 248 219 88 240 234 96 PGMEA = 349 1.0 251 216 236 227 7/3 351
1.0 242 214 243 230 Example 20 Polymer 17 PGMEA 412 2.2 0.5 323 239
75 323 390 93 413 2.0 325 235 325 383 411 2.1 324 251 324 373 PGME
416 0.8 0.2 328 217 66 322 297 92 417 0.9 325 213 318 292 411 0.8
327 220 326 300 PGME/ 412 1.5 0.3 319 222 69 320 296 92 PGMEA = 419
1.2 322 222 327 299 7/3 413 1.1 328 224 322 296 Example 21 Polymer
18 PGMEA 398 121 30 347 347 99 326 322 99 395 143 344 339 325 322
390 93 342 340 322 318 PGME 396 7.2 1.8 350 340 96 324 320 99 396
8.3 345 340 326 322 390 6.1 343 319 329 327 PGME/ 393 36 9.4 375
261 71 322 318 99 PGMEA = 399 39 375 249 325 322 7/3 390 36 359 278
323 321 Example 22 Polymer 19 PGMEA 233 3.3 3.0 156 153 99 144 143
100 235 9.6 156 155 140 142 231 7.8 154 153 139 138 PGME 235 3.4
2.2 155 111 71 140 130 95 232 7.8 155 107 141 135 230 4.4 153 112
145 138 PGME/ 234 5.4 2.5 154 110 76 142 138 95 PGMEA = 236 5.9 155
119 142 136 7/3 230 6.0 154 121 140 130 *Calculated from three
points of average values
TABLE-US-00004 TABLE 4 80.degree. C. for 5 hours under 200.degree.
C. for 10 minutes in 200.degree. C. for 30 minutes in reduced
pressure nitrogen atmosphere nitrogen atmosphere Residual Residual
Residual .alpha. .beta. film rate .alpha. .beta. film rate .alpha.
.beta. film rate Solvent (nm) (nm) (%)* (nm) (nm) (%)* (nm) (nm)
(%)* Example 23 Polymer 20 PGMEA 392 59 10 251 248 100 230 231 100
393 41 251 249 235 236 383 16 242 250 233 232 PGME 387 38 10 240
238 100 234 235 100 382 42 240 241 233 232 388 41 248 247 233 233
PGME/ 390 36 10 241 234 98 232 231 100 PGMEA = 392 42 240 238 232
231 7/3 393 39 246 240 235 238 Example 24 Polymer 21 PGMEA 406 2.2
0.8 320 260 79 318 303 97 402 3.5 316 245 316 308 403 3.8 315 248
315 309 PGME 410 29 6.2 318 230 74 317 297 93 405 22 319 238 317
288 405 25 320 240 310 294 PGME/ 408 22.0 6.0 317 240 76 315 290 94
PGMEA = 407 30.0 310 241 314 300 7/3 402 21.0 313 231 315 296
Example 25 Polymer 22 PGMEA 358 102 31 307 303 99 296 296 100 345
108 304 301 295 296 340 110 302 299 292 293 PGME 346 84 26 310 302
98 294 296 100 356 95 305 299 296 296 340 90 303 297 299 298 PGME/
343 95 27 305 296 97 292 293 100 PGMEA = 349 90 305 299 295 295 7/3
340 93 309 301 293 291 Example 26 10 parts by PGMEA 410 2.1 0.5 320
301 95 316 314 100 mass of 408 2.1 318 305 309 312 polymer 17 411
1.9 315 299 312 311 0.3 parts by PGME 407 0.9 0.2 319 300 94 311
313 100 mass of 409 0.7 316 298 314 314 crosslinking 405 0.7 318
295 308 309 agent (EEC) PGME/ 412 1.3 0.3 316 299 94 312 314 100
PGMEA = 407 1.3 319 301 316 315 7/3 406 1.2 315 297 310 309
Comparative PHS PGMEA 395 0.2 0.2 364 1.7 0.4 359 2.0 0.6 Example 3
400 1.6 375 1.8 356 1.8 394 0.3 372 1.4 358 2.2 PGME 396 0.4 0.1
370 1.3 0.4 355 1.8 0.5 399 0.5 374 1.2 356 1.6 397 0.4 375 1.6 358
1.9 PGME/ 397 0.3 0.1 375 1.6 0.4 360 2.1 0.5 PGMEA = 396 0.8 373
1.2 358 1.6 7/3 398 0.4 373 1.8 355 2.0 Comparative Polymer 23
PGMEA 336 1.3 0.3 296 1.8 0.5 282 2.0 0.8 Example 4 335 1.0 300 1.2
283 2.8 340 1.0 297 1.5 279 2.2 PGME 332 80 25 305 83 27 276 79 28
339 86 302 80 274 73 330 86 301 81 276 76 PGME/ 333 109 33 298 106
35 280 98 35 PGMEA = 335 114 301 102 278 99 7/3 336 112 300 105 278
92 Comparative Polymer 24 PGMEA 365 Impossible to 325 Impossible to
314 Impossible to Example 5 364 measure due to 328 measure due to
320 measure due to 368 whitening after 331 whitening after 320
whitening after immersion in PGMEA immersion in PGMEA immersion in
PGMEA PGME 366 Impossible to 326 Impossible to 316 Impossible to
364 measure due to 320 measure due to 317 measure due to 363
whitening after 323 whitening after 314 whitening after immersion
in PGME immersion in PGME immersion in PGME PGME/ 367 Impossible to
324 Impossible to 320 Impossible to PGMEA = 357 measure due to 325
measure due to 318 measure due to 7/3 365 whitening after 325
whitening after 215 whitening after immersion in immersion in
immersion in PGMEA/PGMEA (7/3) PGMEA/PGMEA (7/3) PGMEA/PGMEA (7/3)
*Calculated from three points of average values
Example 27
[0578] A solution containing PGMEA and cyclohexanone at a mass
ratio (PGMEA/cyclohexanone) of 5/5 in which 10% by mass of the
polymer 18 obtained in Example 21 was dissolved was prepared, and a
30 mm square silicon wafer was spin-coated with the obtained
solution under conditions of 1000 rpm for 10 sec. Next, the
resulting sample was heated at 200.degree. C. for 1 minute in a
nitrogen atmosphere. This wafer was spin-coated with a PGMEA
solution in which 10% by mass of titanium tetraisopropoxide was
dissolved after being cooled to room temperature under conditions
of 1000 rpm for 10 sec. Next, a wafer formed by heating 200.degree.
C. for 1 minute in a nitrogen atmosphere and overcoating the layer
of the polymer 18 with TiO.sub.2 was obtained.
[0579] As the result of observation of the cross section thereof
using a TEM, the interface between the polymer 18 and TiO.sub.2 was
clear and flat.
Example 28
[0580] A wafer formed by overcoating the layer of the polymer 19
with TiO.sub.2 was obtained in the same manner as that in Example
27 except that the polymer 18 was changed to the polymer 19
obtained in Example 22.
[0581] As the result of observation of the cross section thereof
using a TEM, the interface between the polymer 19 and TiO.sub.2 was
clear and flat. The microphotograph of the cross section is shown
in FIG. 4.
Comparative Example 6
[0582] A wafer formed by overcoating the layer of the PHS with
TiO.sub.2 was obtained in the same manner as that in Example 27
except that the polymer 18 was changed to polyhydroxystyrene
(PHS).
[0583] As the result of observation of the cross section thereof
using a TEM, the interface between PHS and TiO.sub.2 was not clear.
Therefore, it was considered that PHS was dissolved and completely
mixed with TiO.sub.2 at the time of spin-coating the layer with the
PGMEA solution of titanium tetraisopropoxide.
[0584] Based on the results described above, in a case where the
material of the present invention is used as a resist underlayer
film, it was found that the uneven surface of the wafer can be made
flat, and intermixing between the intermediate layer or the resist
layer and the resist underlayer film does not occur at the time of
spin-coating the resist underlayer film with the intermediate layer
or the resist layer.
[0585] The material for forming an underlayer film according to the
first present invention enables provision of a resist underlayer
film having sufficient optical characteristics, etching resistance,
excellent flatness, and a suppressed amount of volatile components.
Accordingly, in a semiconductor device manufacturing step, it is
possible to obtain a semiconductor circuit with high
integration.
[0586] The material for forming an underlayer film according to the
second present invention enables realization of a laminate having
excellent adhesiveness between the intermediate layer and the
resist underlayer film and excellent flatness. Accordingly, in the
semiconductor device manufacturing step, it is possible to obtain a
semiconductor circuit with high integration.
[0587] This application claims priority based on Japanese Patent
Application No. 2017-108506 filed on May 31, 2017 and Japanese
Patent Application No. 2017-196260 filed on Oct. 6, 2017, the
entire disclosure of which is incorporated herein.
[0588] The present invention includes the following aspects.
[0589] 1.
[0590] A material for forming an underlayer film which is used to
form a resist underlayer film used in a multi-layer resist process,
the material including:
[0591] a cyclic olefin polymer which has a repeating structural
unit [A] represented by Formula (1) and a repeating structural unit
[B] represented by Formula (2),
[0592] In which a molar ratio [A]/[B] of the structural unit [A] to
the structural unit [B] in the cyclic olefin polymer is greater
than or equal to 5/95 and less than or equal to 95/5.
##STR00010##
[0593] (In Formula (1), at least one of R.sup.1 to R.sup.4 is
selected from hydrogen, an alkyl group having 1 to 10 carbon atoms,
an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1
to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms,
an alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 10
carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms,
an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.1 to R.sup.4 may be bonded to one another to form a ring
structure, and n represents an integer of 0 to 2.)
##STR00011##
[0594] (In Formula (2), at least one of R.sup.5 to R.sup.8 is
selected from hydrogen, an alkyl group having 1 to 10 carbon atoms,
an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1
to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms,
an alkoxyalkyl group having 2 to 10 carbon atoms, an aryloxyalkyl
group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2
to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 10
carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms,
an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms, an
alkoxycarbonylaryl group having 8 to 30 carbon atoms, an
aryloxycarbonylalkyl group having 8 to 20 carbon atoms, an
alkoxyalkyloxycarbonyl group having 3 to 20 carbon atoms, and an
alkoxycarbonylalkyloxycarbonyl group having 4 to 30 carbon atoms,
R.sup.5 to R.sup.8 may be bonded to one another to form a ring
structure, n represents an integer of 0 to 2, and X.sub.1
represents --O-- or --S--.)
[0595] 2.
[0596] The material for forming an underlayer film according to
1.,
[0597] in which a temperature showing an intersection between a
storage modulus (G') curve and a loss modulus (G'') curve in a
solid viscoelasticity of the cyclic olefin polymer which are
measured under conditions of a measurement temperature range of
50.degree. C. to 250.degree. C., a heating rate of 3.degree.
C./min, and a frequency of 1 Hz in a nitrogen atmosphere in a shear
mode using a rheometer is higher than or equal to 80.degree. C. and
lower than or equal to 2000.
[0598] 3.
[0599] The material for forming an underlayer film according to 1.
or 2.,
[0600] in which an amount of a volatile component in the cyclic
olefin polymer which is measured using the following method 1 is
greater than or equal to 0.0% by mass to 1.0% by mass in a case
where a total amount of the cyclic olefin polymer is set to 100% by
mass.
(Method 1: the cyclic olefin polymer is dissolved in
tetrahydrofuran to prepare a solution having a solid content
concentration of 20% by mass, the obtained solution is weighed
using an aluminum plate, heated at 200.degree. C. for 3 minutes in
a nitrogen flow so that the tetrahydrofuran is removed, and cooled
to room temperature so that the cyclic olefin polymer is
solidified, the cyclic olefin polymer is heated in a temperature
range of 30.degree. C. to 300.degree. C. at a heating rate of
10.degree. C./min in a nitrogen atmosphere, and the amount of the
volatile component in the cyclic olefin polymer is calculated based
on a weight reduction amount in a temperature range of 100.degree.
C. to 250.degree. C.)
[0601] 4.
[0602] The material for forming an underlayer film according to any
one of 1. to 3.,
[0603] in which a weight-average molecular weight (Mw) of the
cyclic olefin polymer in terms of polystyrene which is measured
using gel permeation chromatography is greater than or equal to
1000 and less than or equal to 20000.
[0604] 5.
[0605] The material for forming an underlayer film according to any
one of 1. to 4.,
[0606] in which a refractive index (n value) of the cyclic olefin
polymer at a wavelength of 193 nm which is measured using the
following method 2 is greater than or equal to 1.5 and less than or
equal to 2.0.
(Method 2: a coating film which is formed of the cyclic olefin
polymer and has a thickness of 250 nm is formed on a silicon wafer,
and the refractive index (n value) of the obtained coating film at
a wavelength of 193 nm is set as the refractive index (n value) of
the cyclic olefin polymer)
[0607] 6.
[0608] The material for forming an underlayer film according to any
one of 1. to 5.,
[0609] in which an extinction coefficient (k value) of the cyclic
olefin polymer which is measured using the following method 3 is
greater than or equal to 0.0001 and less than or equal to 0.5.
(Method 3: a coating film which is formed of the cyclic olefin
polymer and has a thickness of 250 nm is formed on a silicon wafer,
and the extinction coefficient (k value) of the obtained coating
film is set as the extinction coefficient (k value) of the cyclic
olefin polymer)
[0610] 7.
[0611] The material for forming an underlayer film according to any
one of 1. to 6.,
[0612] which is formed on an uneven structure of a substrate having
the uneven structure and is used for an underlayer film for
embedding a recess in the uneven structure.
[0613] 8.
[0614] A material for forming an underlayer film which is used to
form a resist underlayer film used in a multi-layer resist
process,
[0615] in which the material for forming an underlayer film is a
material of a film containing a cyclic olefin polymer,
[0616] the cyclic olefin polymer is soluble in an organic solvent
at any concentration of at least greater than or equal to 0.01% by
mass and less than or equal to 50% by mass, and
[0617] a residual film rate of the cyclic olefin polymer in the
film which is measured using the following method 4 is greater than
or equal to 50% and less than or equal to 100%.
(method 4: a coating film which is formed of the cyclic olefin
polymer and has a thickness (.alpha.) of greater than or equal to
200 nm and less than or equal to 500 nm is formed on a silicon
wafer, the obtained coating film is treated at 200.degree. C. for
10 minutes, immersed in an organic solvent (propylene
glycol-1-monomethyl ether-2-acetate (PGMEA)) at 23.degree. C. for
10 minutes, and dried under conditions of 150.degree. C. for 3
minutes, and a remaining solvent in the coating film is removed, a
thickness (.beta.) of the coating film obtained by removing the
remaining solvent is measured, and the residual film rate
(=.beta./.alpha..times.100) (%) is calculated)
[0618] 9.
[0619] The material for forming an underlayer film according to
8.,
[0620] in which the cyclic olefin polymer has a repeating
structural unit [A] represented by Formula (1) and a repeating
structural unit [B] represented by Formula (2),
[0621] a molar ratio [A]/[B] of the structural unit [A] to the
structural unit [B] in the cyclic olefin polymer is greater than or
equal to 5/95 and less than or equal to 95