U.S. patent application number 14/021769 was filed with the patent office on 2014-01-09 for asymmetric monoanthracene derivative, material for organic electroluminescent device and organic electroluminescent device utilizing the same.
This patent application is currently assigned to IDEMITSU KOSAN, CO.. The applicant listed for this patent is Masakazu Funahashi, Mineyuki KUBOTA. Invention is credited to Masakazu Funahashi, Mineyuki KUBOTA.
Application Number | 20140008640 14/021769 |
Document ID | / |
Family ID | 34649960 |
Filed Date | 2014-01-09 |
United States Patent
Application |
20140008640 |
Kind Code |
A1 |
KUBOTA; Mineyuki ; et
al. |
January 9, 2014 |
ASYMMETRIC MONOANTHRACENE DERIVATIVE, MATERIAL FOR ORGANIC
ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE
UTILIZING THE SAME
Abstract
Provided are an asymmetric monoanthracene derivative having a
specific structure, a material for an organic EL device comprising
the above asymmetric monoanthracene derivative and an organic EL
device in which an organic thin film layer comprising a single
layer or plural layers including a luminescent layer is interposed
between a cathode and an anode, wherein at least one of the above
organic thin film layers contains the asymmetric monoanthracene
derivative described above in the form of a single component or a
mixed component. Provided are an organic electroluminescent (EL)
device having a high luminous efficiency and a long life, an
asymmetric monoanthracene derivative which materializes the same
and a material for an organic EL device.
Inventors: |
KUBOTA; Mineyuki;
(Sodegaura-shi, JP) ; Funahashi; Masakazu;
(Sodegaura-shi, JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
KUBOTA; Mineyuki
Funahashi; Masakazu |
Sodegaura-shi
Sodegaura-shi |
|
JP
JP |
|
|
Assignee: |
IDEMITSU KOSAN, CO.
Tokyo
JP
|
Family ID: |
34649960 |
Appl. No.: |
14/021769 |
Filed: |
September 9, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10572586 |
Mar 20, 2006 |
8568902 |
|
|
PCT/JP04/18111 |
Nov 30, 2004 |
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14021769 |
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Current U.S.
Class: |
257/40 |
Current CPC
Class: |
H05B 33/14 20130101;
C07C 2603/26 20170501; C09K 2211/1014 20130101; C07C 15/30
20130101; C07C 15/38 20130101; C09K 2211/1011 20130101; C07C
2603/24 20170501; H01L 51/5012 20130101; C09K 2211/1007 20130101;
C09K 2211/1048 20130101; H01L 51/0059 20130101; H01L 2251/308
20130101; H01L 51/006 20130101; H01L 51/0081 20130101; H01L 51/0058
20130101; C09K 11/06 20130101; C07C 2603/50 20170501; C07C 15/28
20130101; H01L 51/0052 20130101; C07C 13/573 20130101 |
Class at
Publication: |
257/40 |
International
Class: |
H01L 51/00 20060101
H01L051/00 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 1, 2003 |
JP |
2003-401038 |
Claims
1-13. (canceled)
14. An organic electroluminescent device in which an organic thin
film layer comprising a single layer or plural layers including a
luminescent layer is interposed between a cathode and an anode,
wherein at least one of the above organic thin film layers contains
an asymmetric monoanthracene derivative represented by formula (1)
and an arylamine compound represented by the following Formula (B):
##STR00031## wherein Ar.sup.1 and Ar.sup.2 each are independently a
substituted or non-substituted aromatic hydrocarbon ring group
having 6 to 50 nuclear carbon atoms, and m and n each are an
integer of 1 to 4, provided that when m and n are 1 and the bonding
positions of Ar.sup.1 and Ar.sup.2 in the benzene wrings are
symmetric in right and left, Ar.sup.1 is not the same as Ar.sup.2
and that when m or n is an integer of 2 to 4, m and n are different
integers; R.sup.1 to R.sup.8 each are independently a hydrogen
atom, a substituted or non-substituted aromatic hydrocarbon ring
group having 5 to 50 nuclear carbon atoms, a substituted or
non-substituted aromatic heterocyclic group having 5 to 50 nuclear
atoms, a substituted or non-substituted alkyl group having 1 to 50
carbon atoms, a substituted or non-substituted cycloalkyl group, a
substituted or non-substituted alkoxy group having 1 to 50 carbon
atoms, a substituted or non-substituted aralkyl group having 6 to
50 carbon atoms, a substituted or non-substituted aryloxy group
having 5 to 50 nuclear atoms, a substituted or non-substituted
arylthio group having 5 to 50 nuclear atoms, a substituted or
non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a
substituted or non-substituted silyl group, a carboxyl group, a
halogen atom, a cyano group, a nitro group or a hydroxyl group;
R.sup.9 and R.sup.10 each are independently a hydrogen atom, a
substituted or non-substituted aromatic hydrocarbon ring group
having 5 to 50 nuclear carbon atoms, a substituted or
non-substituted alkyl group having 1 to 50 carbon atoms, a
substituted or non-substituted cycloalkyl group, a substituted or
non-substituted alkoxy group having 1 to 50 carbon atoms, a
substituted or non-substituted aralkyl group having 6 to 50 carbon
atoms, a substituted or non-substituted aryloxy group having 5 to
50 nuclear atoms, a substituted or non-substituted arylthio group
having 5 to 50 nuclear atoms, a substituted or non-substituted
alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or
non-substituted silyl group, a carboxyl group, a halogen atom, a
cyano group, a nitro group or a hydroxyl group, and any groups are
not an alkenyl group; and R.sup.1 to R.sup.10, Ar.sup.1 and
Ar.sup.2 are not an anthracenyl group and fluorenyl group,
##STR00032## wherein in formula (B): Ar.sup.6 to Ar.sup.8 each
independently represents a substituted or unsubstituted aryl group
having 5 to 40 carbon atoms forming the aromatic ring, and q
represents an integer of 1 to 4.
15. The organic electroluminescent device as described in claim 14,
wherein the Formula (1) is the following Formula (2): ##STR00033##
wherein Ar.sup.1 and Ar.sup.2 each are independently a substituted
or non-substituted aromatic hydrocarbon rang group having 6 to 50
nuclear carbon atoms, and n is an integer of 1 to 4, provided that
when n is 1 and the bonding positions of Ar.sup.1 and Ar.sup.2 in
the benzene ring are symmetric in right and left, Ar.sup.1 is not
the same as Ar.sup.2; R.sup.1 to R.sup.8 each are independently a
hydrogen atom, a substituted or non-substituted aromatic
hydrocarbon rang group having 6 to 50 nuclear carbon atoms, a
substituted or non-substituted aromatic heterocyclic group having 5
to 50 nuclear atoms, a substituted or non-substituted alkyl group
having 1 to 50 carbon atoms, a substituted or non-substituted
cycloalkyl group, a substituted or non-substituted alkoxy group
having 1 to 50 carbon atoms, a substituted or non-substituted
aralkyl group having 6 to 50 carbon atoms, a substituted or
non-substituted aryloxy group having 5 to 50 nuclear atoms, a
substituted or non-substituted arylthio group having 5 to 50
nuclear atoms, a substituted or non-substituted alkoxycarbonyl
group having 1 to 50 carbon atoms, a substituted or non-substituted
silyl group, a carboxyl group, a halogen atom, a cyano group, a
nitro group or a hydroxyl group; R.sup.9 and R.sup.10 each are
independently a hydrogen atom, a substituted or non-substituted
aromatic hydrocarbon ring group having 6 to 50 nuclear carbon
atoms, a substituted or non-substituted alkyl group having 1 to 50
carbon atoms, a substituted or non-substituted cycloalkyl group, a
substituted or non-substituted alkoxy group having 1 to 50 carbon
atoms, a substituted or non-substituted aralkyl group having 6 to
50 carbon atoms, a substituted or non-substituted aryloxy group
having 5 to 50 nuclear atoms, a substituted or non-substituted
arylthio group having 5 to 50 nuclear atoms, a substituted or
non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a
substituted or non-substituted silyl group, a carboxyl group, a
halogen atom, a cyano group, a nitro group or a hydroxyl group, and
any groups are not an alkenyl group; and R.sup.1 to R.sup.10,
Ar.sup.1 and Ar.sup.2 are not an anthracenyl group and fluorenyl
group.
16. The organic electroluminescent device as described in claim 14,
wherein the Formula (1) is the following Formula (3): ##STR00034##
wherein Ar.sup.1 and Ar.sup.2 each are independently a substituted
or non-substituted aromatic hydrocarbon ring group having 6 to 50
nuclear carbon atoms, and n is an integer of 1 to 4, provided that
when n is 1 and the bonding positions of Ar.sup.1 and Ar.sup.2 in
the benzene ring are symmetric in right and left, Ar.sup.1 is not
the same as Ar.sup.2; R.sup.1 to R.sup.8 each are independently a
hydrogen atom, a substituted or non-substituted aromatic
hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a
substituted or non-substituted aromatic heterocyclic group having 5
to 50 nuclear atoms, a substituted or non-substituted alkyl group
having 1 to 50 carbon atoms, a substituted or non-substituted
cycloalkyl group, a substituted or non-substituted alkoxy group
having 1 to 50 carbon atoms, a substituted or non-substituted
aralkyl group having 6 to 50 carbon atoms, a substituted or
non-substituted aryloxy group having 5 to 50 nuclear atoms, a
substituted or non-substituted arylthio group having 5 to 50
nuclear atoms, a substituted or non-substituted alkoxycarbonyl
group having 1 to 50 carbon atoms, a substituted or non-substituted
silyl group, a carboxyl group, a halogen atom, a cyano group, a
nitro group or a hydroxyl group; R.sup.9 and R.sup.10 each are
independently a hydrogen atom, a substituted or non-substituted
aromatic hydrocarbon ring group having 6 to 50 nuclear carbon
atoms, a substituted or non-substituted alkyl group having 1 to 50
carbon atoms, a substituted or non-substituted cycloalkyl group, a
substituted or non-substituted alkoxy group having 1 to 50 carbon
atoms, a substituted or non-substituted aralkyl group having 6 to
50 carbon atoms, a substituted or non-substituted aryloxy group
having 5 to 50 nuclear atoms, a substituted or non-substituted
arylthio group having 5 to 50 nuclear atoms, a substituted or
non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a
substituted or non-substituted silyl group, a carboxyl group, a
halogen atom, a cyano group, a nitro group or a hydroxyl group, and
any groups are not an alkenyl group; and R.sup.1 to R.sup.10,
Ar.sup.1 and Ar.sup.2 are not an anthracenyl group and fluorenyl
group.
17. The organic electroluminescent device as described in claim 14,
wherein the Formula (1) is the following Formula (4): ##STR00035##
wherein Ar.sup.1 and Ar.sup.2 each are independently a substituted
or non-substituted aromatic hydrocarbon ring group having 6 to 50
nuclear carbon atoms, and n is an integer of 1 to 4, provided that
when n is 1 and the bonding positions of Ar.sup.1 and Ar.sup.2 in
the benzene ring are symmetric in right and left, Ar.sup.1 is not
the same as Ar.sup.2; R.sup.1 to R.sup.8 each are independently a
hydrogen atom, a substituted or non-substituted aromatic
hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a
substituted or non-substituted aromatic heterocyclic group having 5
to 50 nuclear atoms, a substituted or non-substituted alkyl group
having 1 to 50 carbon atoms, a substituted or non-substituted
cycloalkyl group, a substituted or non-substituted alkoxy group
having 1 to 50 carbon atoms, a substituted or non-substituted
aralkyl group having 6 to 50 carbon atoms, a substituted or
non-substituted aryloxy group having 5 to 50 nuclear atoms, a
substituted or non-substituted arylthio group having 5 to 50
nuclear atoms, a substituted or non-substituted alkoxycarbonyl
group having 1 to 50 carbon atoms, a substituted or non-substituted
silyl group, a carboxyl group, a halogen atom, a cyano group, a
nitro group or a hydroxyl group; R.sup.9 and R.sup.10 each are
independently a hydrogen atom, a substituted or non-substituted
aromatic hydrocarbon ring group having 6 to 50 nuclear carbon
atoms, a substituted or non-substituted alkyl group having 1 to 50
carbon atoms, a substituted or non-substituted cycloalkyl group, a
substituted or non-substituted alkoxy group having 1 to 50 carbon
atoms, a substituted or non-substituted aralkyl group having 6 to
50 carbon atoms, a substituted or non-substituted aryloxy group
having 5 to 50 nuclear atoms, a substituted or non-substituted
arylthio group having 5 to 50 nuclear atoms, a substituted or
non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a
substituted or non-substituted silyl group, a carboxyl group, a
halogen atom, a cyano group, a nitro group or a hydroxyl group, and
any groups are not an alkenyl group; and R.sup.1 to R.sup.10,
Ar.sup.1 and Ar.sup.2 are not an anthracenyl group and fluorenyl
group.
18. The organic electroluminescent device as described in claim 14,
wherein in Formula (1), Ar.sup.1 and Ar.sup.2 described above each
are independently any of phenyl, 1-naphthyl, 2-naphthyl,
9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl,
1-pyrenyl, 2-pyxenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl,
4-biphenylyl, o-tolyl, m-tolyl, p-tolyl and p-t-butylphenyl.
19. The organic electroluminescent device as described in claim 14,
wherein in Formula (1), Ar.sup.1 and Ar.sup.2 described above each
are independently any of phenyl, 1-naphthyl, 2-naphthyl and
9-phenanthryl.
20. The organic electroluminescent device as described in claim 14,
wherein the asymmetric monoanthracene derivative represented by
formula (1) is a host material.
Description
TECHNICAL FIELD
[0001] The present invention relates to an asymmetric
monoanthracene derivative, a material for an organic
electroluminescent device and an organic electroluminescent device
making use of it, more specifically to an organic
electroluminescent device having a high luminous efficiency and a
long life, an asymmetric monoanthracene derivative which
materializes the same and a material for an organic
electroluminescent device.
BACKGROUND ART
[0002] An organic electroluminescent device (hereinafter
"electroluminescent" shall be abbreviated as EL) is a spontaneous
luminescent device making use of the principle that a fluorescent
substance emits light by recombination energy of holes injected
from an anode and electrons injected from a cathode by applying an
electric field. Since a low voltage-driven organic EL device of a
laminate type was reported by C. W. Tang of Eastman Kodak Company
(C. W. Tang and S. A. Vanslyke, Applied Physics Letters, Vol. 51,
p. 913, 1987), researches on organic EL devices comprising organic
materials as structural materials have actively been carried out.
Tang et al. use tris(8-hydroxyquinolinolaluminum) for the
luminescent layer and a triphenyldiamine derivative for the hole
transporting layer. The advantages of a laminate structure include
an elevation in an efficiency of injecting holes into a luminescent
layer, a rise in a forming efficiency of excitons formed by
blocking electrons injected from a cathode to recombine them and
shutting up of excitons formed in the luminescent layer. As shown
in the above example, a two layer type comprising a hole
transporting (injecting) layer and an electron transporting and
luminescent layer and a three layer type comprising a hole
transporting (injecting) layer, a luminescent layer and an electron
transporting (injecting) layer are well known as the device
structures of the organic EL device. In such laminate type
structural devices, device structures and forming methods are
studied in order to enhance a recombination efficiency of holes and
electrons injected.
[0003] Known as luminescent materials are luminescent materials
such as chelate complexes such as a tris(8-quinolinolate)aluminum
complex, coumarin derivatives, tetraphenylbutadiene derivatives,
bisstyrylarylene derivatives and oxadiazole derivatives. It is
reported that luminescence of a blue color to a red color in a
visible region is obtained from them, and it is expected that a
color display device is materialized (for example, patent document
1, patent document 2 and patent document 3).
[0004] Further, a device using a phenylanthracene derivative as a
luminescent material is disclosed in patent document 4. Such
anthracene derivative is used as a blue color luminescent material,
and it has been desired to extend the device life. A material
having a naphthyl group in 9 and 10 positions of anthracene is
disclosed in patent document 5, and a material having a
fluoranthene group in 9 and 10 positions of anthracene is disclosed
in patent document 6. These anthracene derivatives are also used as
a blue color luminescent material, and it has been desired as well
to improve the device life. Further, it is disclosed in patent
document 7 to use various anthracene derivatives as a hole
transporting material. However, they have not yet been evaluated as
a luminescent material. [0005] [Patent document 1]: Japanese Patent
Application Laid-Open No. 239655/1996 [0006] [Patent document 2]:
Japanese Patent Application Laid-Open No. 138561/1995 [0007]
[Patent document 3]: Japanese Patent Application Laid-Open No.
200289/1991 [0008] [Patent document 4]: Japanese Patent Application
Laid-Open No. 012600/1996 [0009] [Patent document 5]: Japanese
Patent Application Laid-Open No. 3782/1999 [0010] [Patent document
6]: Japanese Patent Application Laid-Open No. 257074/2001 [0011]
[Patent document 7]: Japanese Patent Application Laid-Open No.
182776/2000
Disclosure of the Invention
[0012] The present invention has been made in order to solve the
problems described above, and an object thereof is to provide an
organic EL device having a high luminous efficiency and a long
life, an asymmetric monoanthracene derivative which materializes
the same and a material for an organic EL device.
[0013] Intensive researches repeated by the present inventors in
order to achieve the object described above have resulted in
finding that if a compound having a specific monoanthracene
structure of an asymmetric type represented by Formula (1) shown
below is used as a luminescent material in an organic EL device,
the organic EL device having a high luminous efficiency and a long
life is obtained, and thus they have come to complete the present
invention. Further, use of the compound having a specific
monoanthracene structure of an asymmetric type represented by
Formula (1) shown below makes it possible to lower a depositing
temperature of the compound and inhibits the compound from being
thermally decomposed in deposition.
[0014] That is, the present invention provides an asymmetric
monoanthracene derivative represented by Formula (1) shown below, a
material for an organic EL device comprising the above asymmetric
monoanthracene derivative and an organic EL device in which an
organic thin film layer comprising a single layer or plural layers
including a luminescent layer is interposed between a cathode and
an anode, wherein at least one of the above organic thin film
layers contains the asymmetric monoanthracene derivative
represented by Formula (1) in the form of a single component or a
mixed component:
##STR00001##
wherein Ar.sup.1 and Ar.sup.2 each are independently a substituted
or non-substituted aromatic hydrocarbon ring group having 6 to 50
nuclear carbon atoms, and m and n each are an integer of 1 to 4,
provided that when m and n are 1 and the bonding positions of
Ar.sup.1 and Ar.sup.2 in the benzene rings are symmetric in right
and left, Ar.sup.1 is not the same as Ar.sup.2 and that when m or n
is an integer of 2 to 4, m and n are different integers.
[0015] R.sup.1 to R.sup.8 each are independently a hydrogen atom, a
substituted or non-substituted aromatic hydrocarbon ring group
having 6 to 50 nuclear carbon atoms, a substituted or
non-substituted aromatic heterocyclic group having 5 to 50 nuclear
atoms, a substituted or non-substituted alkyl group having 1 to 50
carbon atoms, a substituted or non-substituted cycloalkyl group, a
substituted or non-substituted alkoxy group having 1 to 50 carbon
atoms, a substituted or non-substituted aralkyl group having 6 to
50 carbon atoms, a substituted or non-substituted aryloxy group
having 5 to 50 nuclear atoms, a substituted or non-substituted
arylthio group having 5 to 50 nuclear atoms, a substituted or
non-substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a
substituted or non-substituted silyl group, a carboxyl group, a
halogen atom, a cyano group, a nitro group or a hydroxyl group.
[0016] R.sup.9 to R.sup.10 each are independently a hydrogen atom,
a substituted or non-substituted aromatic hydrocarbon ring group
having 6 to 50 nuclear carbon atoms, a substituted or
non-substituted alkyl group having 1 to 50 carbon atoms, a
substituted or non-substituted cycloalkyl group, a substituted or
non-substituted alkoxy group having 1 to 50 carbon atoms, a
substituted or non-substituted aralkyl group having 6 to 50 carbon
atoms, a substituted or non-substituted aryloxy group having 5 to
50 nuclear atoms, a substituted or non-substituted arylthio group
having 5 to 50 nuclear atoms, a substituted or non-substituted
alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or
non-substituted silyl group, a carboxyl group, a halogen atom, a
cyano group, a nitro group or a hydroxyl group, and any groups are
not an alkenyl group.
Effect of the Invention
[0017] An organic EL device prepared by using the asymmetric
monoanthracene derivative of the present invention as a material
for the organic EL device has a high luminous efficiency and a long
life.
BEST MODE FOR CARRYING OUT THE INVENTION
[0018] The asymmetric monoanthracene derivative of the present
invention is represented by Formula (1) described above.
[0019] In Formula (1) described above, m and n each are an integer
of 1 to 4, and they are preferably an integer of 1 to 2.
[0020] Provided that when m and n are 1 and the bonding positions
of Ar.sup.1 and Ar.sup.2 in the benzene ring are symmetric in right
and left, Ar.sup.1 is not the same as Ar.sup.2 and that when m or n
is an integer of 2 to 4, m and n are different integers. In the
present invention, the symmetric type in right and left means a
case where when Ar.sup.1 and R.sup.9 are substituted in an X.sup.1
position and an X.sup.2 position in the benzene ring bonded to a 9
position of the anthracene ring, Ar.sup.2 and R.sup.10 also are
substituted respectively in an X.sup.1 position and an X.sup.2
position in the benzene ring bonded to a 10 position of the
anthracene ring.
[0021] That is, the anthracene derivative represented by Formula
(1) assumes a structure in which the right and left benzene rings
bonded to the anthracene ring and substituted with the aromatic
hydrocarbon ring groups are asymmetric in right and left, and the
anthracene derivative described above has an asymmetric
structure.
[0022] For example, if substituents in a 2 position and a 3
position in the anthracene nucleus are different but substituents
bonded to a 9 position and a 10 position are the same, it is not
included in the asymmetric type defined in the present
invention.
[0023] The derivative in which m and/or n are 1 in Formula (1)
described above is more preferred, and when m is, for example, 1,
the derivative represented by any of Formulas (2) to (4) is further
preferred:
##STR00002##
[0024] In Formulas (2) to (4), Ar.sup.1, Ar.sup.2, n and R.sup.1 to
R.sup.10 are the same as in Formula (1).
[0025] As is the case with what was described above, in a case
where n is 1 and the positions of Ar.sup.1 and Ar.sup.2 bonded to
the benzene rings are symmetric in right and left, Ar.sup.1 is not
the same as Ar.sup.2.
[0026] In Formula (1), Ar.sup.1 and Ar.sup.2 each are independently
a substituted or non-substituted aromatic hydrocarbon ring group
having 6 to 50 nuclear carbon atoms.
[0027] The substituted or non-substituted aromatic hydrocarbon ring
group represented by Ar.sup.1 and Ar.sup.2 include, for example,
phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl,
1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl,
9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl,
1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl,
4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl,
m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl,
m-tolyl, p-tolyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl,
3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthryl,
4'-methylbiphenylyl and 4''-t-butyl-p-terphenyl-4-yl.
[0028] Among them, preferred are phenyl, 1-naphthyl, 2-naphthyl,
9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl,
1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl,
4-biphenylyl, o-tolyl, m-tolyl, p-tolyl and p-t-butylphenyl.
[0029] In Formula (1), R.sup.1 to R.sup.8 each are independently a
hydrogen atom, a substituted or non-substituted aromatic
hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a
substituted or non-substituted aromatic heterocyclic group having 5
to 50 nuclear atoms, a substituted or non-substituted alkyl group
having 1 to 50 carbon atoms, a substituted or non-substituted
cycloalkyl group, a substituted or non-substituted alkoxy group
having 1 to 50 carbon atoms, a substituted or non-substituted
aralkyl group having 6 to 50 carbon atoms, a substituted or
non-substituted aryloxy group having 5 to 50 carbon atoms, a
substituted or non-substituted arylthio group having 5 to 50
nuclear atoms, a substituted or non-substituted alkoxycarbonyl
group having 1 to 50 carbon atoms, a substituted or non-substituted
silyl group, a carboxyl group, a halogen atom, a cyano group, a
nitro group or a hydroxyl group.
[0030] R.sup.9 to R.sup.10 each are independently a hydrogen atom,
a substituted or non-substituted aromatic hydrocarbon ring group
having 6 to 50 nuclear carbon atoms, a substituted or
non-substituted alkyl group having 1 to 50 carbon atoms, a
substituted or non-substituted cycloalkyl group, a substituted or
non-substituted alkoxy group having 1 to 50 carbon atoms, a
substituted or non-substituted aralkyl group having 6 to 50 carbon
atoms, a substituted or non-substituted aryloxy group having 5 to
50 nuclear atoms, a substituted or non-substituted arylthio group
having 5 to 50 nuclear atoms, a substituted or non-substituted
alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or
non-substituted silyl group, a carboxyl group, a halogen atom, a
cyano group, a nitro group or a hydroxyl group, and any groups are
not an alkenyl group.
[0031] The examples of the substituted or non-substituted aromatic
hydrocarbon ring group represented by R.sup.1 to R.sup.10 include
phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl,
1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl,
9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl,
1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl,
4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl,
m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl,
m-tolyl, p-tolyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl,
3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthryl,
4'-methylbiphenylyl and 4''-t-butyl-p-terphenyl-4-yl.
[0032] The examples of the substituted or non-substituted aromatic
heterocyclic group represented by R.sup.1 to R.sup.8 include
1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl,
3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl,
4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl,
2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl,
6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl,
3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl,
7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl,
4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl,
7-isobenzofuranyl, quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl,
6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl,
4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl,
8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl,
1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl,
9-carbazolyl, 1-phenanthridinyl, 2-phenanthridinyl,
3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl,
7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl,
10-phenanthryldinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl,
4-acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl,
1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl,
1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl,
1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl,
1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl,
1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl,
1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl,
1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl,
1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl,
1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl,
1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl,
1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl,
1,9-phenanthroline-10-yl, 1,10-phenanthroline-2-yl,
1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl,
1,10-phenanthroline-5-yl, 2,9-phenanthroline-1-yl,
2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl,
2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl,
2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl,
2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl,
2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl,
2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl,
2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl,
2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl,
2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl,
2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl,
2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl,
2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl,
1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl,
4-phenothiazinyl, 10-phenothiazinyl, 1-phenoxazinyl,
2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl,
2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl,
3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl,
2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl,
3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl,
3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl,
3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl,
4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl,
2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl and
4-t-butyl-3-indolyl.
[0033] The examples of the substituted or non-substituted alkyl
group represented by R.sup.1 to R'' include methyl, ethyl, propyl,
isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl,
n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl,
2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl,
2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl,
1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl,
1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl,
bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl,
1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl,
1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl,
2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl,
2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl,
2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl,
1,3-diaminoisopropyl, 2,3-diamino-t-butyl, 1,2,3-triaminopropyl,
cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl,
1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl,
1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl,
2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl,
2,3-dinitro-t-butyl and 1,2,3-trinitropropyl.
[0034] The examples of the substituted or non-substituted
cycloalkyl group represented by R.sup.1 to R.sup.10 include
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
4-methylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl and
2-norbornyl.
[0035] The substituted or non-substituted alkoxy group represented
by R.sup.1 to R.sup.10 is a group represented by --OY, and the
examples of Y include methyl, ethyl, propyl, isopropyl, n-butyl,
s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl,
hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl,
1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl,
1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl,
2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl,
2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl,
1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl,
1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromopropyl,
iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl,
1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-t-butyl,
1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl,
2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl,
2,3-diamino-t-butyl, 1,2,3-triaminopropyl, cyanomethyl,
1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl,
1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl,
nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl,
1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-t-butyl and
1,2,3-trinitropropyl.
[0036] The examples of the substituted or non-substituted aralkyl
group represented by R.sup.1 to R.sup.10 include benzyl,
1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl,
phenyl-t-butyl, a-naphthylmethyl, 1-.alpha.-naphthylethyl,
2-.alpha.-naphthylethyl, 1-.alpha.-naphthylisopropyl,
2-.alpha.-naphthylisopropyl, .beta.-naphthylmethyl,
1-.beta.-naphthylethyl, 2-.beta.-naphthylethyl,
1-.beta.-naphthylisopropyl, 2-.beta.-naphthylisopropyl,
1-pyrrolylmethyl, 2-(1-pyrrolyl)ethyl, p-methylbenzyl,
m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl,
o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl,
p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl,
m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl,
o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl,
p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl,
1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl.
[0037] The substituted or non-substituted aryloxy group represented
by R.sup.1 to R.sup.10 is represented by --OY', and the examples of
Y' include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl,
9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl,
4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl,
9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl,
3-biphenylyl, 4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl,
p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl,
m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-t-butylphenyl,
p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl,
4-methyl-1-anthryl, 4'-methylbiphenylyl,
4''-t-butyl-p-terphenyl-4-yl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl,
2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-indolyl, 3-indolyl,
4-indolyl, 5-indonyl, 6-indolyl, 7-indolyl, 1-isoindolyl,
3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl,
7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl,
4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl,
1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl,
5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl,
2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl,
7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl,
4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl,
8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl,
1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl,
1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl,
4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl,
8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl,
1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl,
1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl,
1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl,
1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl,
1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl,
1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl,
1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl,
1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl,
1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl,
1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl,
1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl,
1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl,
1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl,
1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl,
1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl,
2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl,
2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl,
2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl,
2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl,
2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl,
2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl,
2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl,
2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl,
2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl,
2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl,
2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl,
2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl,
2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl,
4-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl,
4-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl,
5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl,
2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl,
2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl,
3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl,
3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl,
4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl,
2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl and
4-t-butyl-3-indolyl.
[0038] The substituted or non-substituted arylthio group
represented by R.sup.1 to R.sup.10 is represented by --SY'', and
the examples of Y'' include phenyl, 1-naphthyl, 2-naphthyl,
1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl,
3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl,
2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl,
2-biphenylyl, 3-biphenylyl, 4-biphenylyl, p-terphenyl-4-yl,
p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl,
m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl,
p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl,
4-methyl-1,-naphthyl, 4-methyl-1-anthryl, 4'-methylbiphenylyl,
4''-t-butyl-p-terphenyl-4-yl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl,
2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-indolyl, 3-indolyl,
4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl,
3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl,
7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl,
4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl,
1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl,
5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl,
2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl,
7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl,
4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl,
8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl,
1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl,
1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl,
4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl,
8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl,
1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl,
1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl,
1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl,
1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl,
1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl,
1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl,
1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl,
1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl,
1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl,
1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl,
1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl,
1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl,
1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl,
1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl,
1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl,
2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl,
2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl,
2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl,
2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl,
2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl,
2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl,
2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl,
2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl,
2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl,
2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl,
2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl,
2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl,
2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl,
4-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl,
4-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl,
5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl,
2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl,
2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl,
3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl,
3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl,
4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl,
2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl and
4-t-butyl-3-indolyl.
[0039] The substituted or non-substituted alkoxylcarbonyl group
represented by R.sup.1 to R.sup.10 is represented by --COOZ, and
the examples of Z include methyl, ethyl, propyl, isopropyl,
n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl,
n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl,
2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl,
2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl,
1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl,
1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl,
bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl,
1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl,
1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl,
2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl,
2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl,
2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl,
1,3-diaminoisopropyl, 2,3-diamino-t-butyl, 1,2,3-triaminopropyl;
cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl,
1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl,
1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl,
2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl,
2,3-dinitro-t-butyl and 1,2,3-trinitropropyl.
[0040] The halogen atom represented by R.sup.1 to R.sup.10 includes
fluorine, chlorine, bromine and iodine.
[0041] Substituents in the groups represented by Ar.sup.1, Ar.sup.2
and R.sup.1 to R.sup.10 each described above include a halogen
atom, a hydroxyl group, a nitro group, a cyano group, an alkyl
group, an aryl group, a cycloalkyl group, an alkoxy group, an
aralkyl group, an aryloxy group, an arylthio group, an
alkoxycarbonyl group or a carboxyl group.
[0042] The specific examples of the asymmetric monoanthracene
derivative represented by Formula (1) in the present invention
shall be shown below, but they shall not be restricted to these
compounds given as the examples.
TABLE-US-00001 ##STR00003## Compound Ar.sup.1 Ar.sup.2 AN-1
1-naphthyl 9-phenanthryl AN-2 1-naphthyl 1-pyrenyl AN-3 1-naphthyl
phenyl AN-4 1-naphthyl 2-biphenyl AN-5 1-naphthyl 3-biphenyl AN-6
1-naphthyl 4-biphenyl AN-7 1-naphthyl 2-p-terphenyl AN-8 2-naphthyl
1-naphthyl AN-9 2-naphthyl 9-phenanthryl AN-10 2-naphthyl 1-pyrenyl
AN-11 2-naphthyl phenyl AN-12 2-naphthyl 2-biphenyl AN-13
2-naphthyl 3-biphenyl AN-14 2-naphthyl 4-biphenyl AN-15 2-naphthyl
2-p-terphenyl AN-16 9-phenanthryl 1-pyrenyl AN-17 9-phenanthryl
phenyl AN-18 9-phenanthryl 2-biphenyl AN-19 9-phenanthryl
3-biphenyl AN-20 9-phenanthryl 4-biphenyl AN-21 9-phenanthryl
2-p-terphenyl AN-22 1-pyrenyl phenyl AN-23 1-pyrenyl 2-biphenyl
AN-24 1-pyrenyl 3-biphenyl AN-25 1-pyrenyl 4-biphenyl AN-26
1-pyrenyl 2-p-terphenyl AN-27 phenyl 2-biphenyl AN-28 phenyl
3-biphenyl AN-29 phenyl 4-biphenyl AN-30 phenyl 2-p-terphenyl AN-31
2-biphenyl 3-biphenyl AN-32 2-biphenyl 4-biphenyl AN-33 2-biphenyl
2-p-terphenyl AN-34 3-biphenyl 4-biphenyl AN-35 3-biphenyl
2-p-terphenyl
TABLE-US-00002 ##STR00004## Compound Ar.sup.1 Ar.sup.2 AN-36
1-naphthyl 1-naphthyl AN-37 1-naphthyl 2-naphthyl AN-38 1-naphthyl
9-phenanthryl AN-39 1-naphthyl 1-pyrenyl AN-40 1-naphthyl phenyl
AN-41 1-naphthyl 2-biphenyl AN-42 1-naphthyl 3-biphenyl AN-43
1-naphthyl 4-biphenyl AN-44 1-naphthyl 2-p-terphenyl AN-45
2-naphthyl 1-naphthyl AN-46 2-naphthyl 2-naphthyl AN-47 2-naphthyl
9-phenanthryl AN-48 2-naphthyl 1-pyrenyl AN-49 2-naphthyl phenyl
AN-50 2-naphthyl 2-biphenyl AN-51 2-naphthyl 3-biphenyl AN-52
2-naphthyl 4-biphenyl AN-53 2-naphthyl 2-p-terphenyl AN-54
9-phenanthryl 1-naphthyl AN-55 9-phenanthryl 2-naphthyl AN-56
9-phenanthryl 9-phenanthryl AN-57 9-phenanthryl 1-pyrenyl AN-58
9-phenanthryl phenyl AN-59 9-phenanthryl 2-biphenyl AN-60
9-phenanthryl 3-biphenyl AN-61 9-phenanthryl 4-biphenyl AN-62
9-phenanthryl 2-p-terphenyl AN-63 1-pyrenyl 1-naphthyl AN-64
1-pyrenyl 2-naphthyl AN-65 1-pyrenyl 9-phenanthryl AN-66 1-pyrenyl
1-pyrenyl AN-67 1-pyrenyl phenyl AN-68 1-pyrenyl 2-biphenyl AN-69
1-pyrenyl 3-biphenyl AN-70 1-pyrenyl 4-biphenyl AN-71 1-pyrenyl
2-p-terphenyl AN-72 phenyl 1-naphthyl AN-73 phenyl 2-naphthyl AN-74
phenyl 9-phenanthryl AN-75 phenyl 1-pyrenyl AN-76 phenyl phenyl
AN-77 phenyl 2-biphenyl AN-78 phenyl 3-biphenyl AN-79 phenyl
4-biphenyl AN-80 phenyl 2-p-terphenyl AN-81 2-biphenyl 1-naphthyl
AN-82 2-biphenyl 2-naphthyl AN-83 2-biphenyl 9-phenanthryl AN-84
2-biphenyl 1-pyrenyl AN-85 2-biphenyl phenyl AN-86 2-biphenyl
2-biphenyl AN-87 2-biphenyl 3-biphenyl AN-88 2-biphenyl 4-biphenyl
AN-89 2-biphenyl 2-p-terphenyl AN-90 3-biphenyl 1-naphthyl AN-91
3-biphenyl 2-naphthyl AN-92 3-biphenyl 9-phenanthryl AN-93
3-biphenyl 1-pyrenyl AN-94 3-biphenyl phenyl AN-95 3-biphenyl
2-biphenyl AN-96 3-biphenyl 3-biphenyl AN-97 3-biphenyl 4-biphenyl
AN-98 3-biphenyl 2-p-terphenyl AN-99 4-biphenyl 1-naphthyl AN-100
4-biphenyl 2-naphthyl AN-101 4-biphenyl 9-phenanthryl AN-102
4-biphenyl 1-pyrenyl AN-103 4-biphenyl phenyl AN-104 4-biphenyl
2-biphenyl AN-105 4-biphenyl 3-biphenyl AN-106 4-biphenyl
4-biphenyl AN-107 4-biphenyl 2-p-terphenyl
TABLE-US-00003 ##STR00005## Compound Ar.sup.1 Ar.sup.2 AN-108
1-naphthyl 1-naphthyl AN-109 1-naphthyl 2-naphthyl AN-110
1-naphthyl 9-phenanthryl AN-111 1-naphthyl 1-pyrenyl AN-112
1-naphthyl phenyl AN-113 1-naphthyl 2-biphenyl AN-114 1-naphthyl
3-biphenyl AN-115 1-naphthyl 4-biphenyl AN-116 1-naphthyl
2-p-terphenyl AN-117 2-naphthyl 1-naphthyl AN-118 2-naphthyl
2-naphthyl AN-119 2-naphthyl 9-phenanthryl AN-120 2-naphthyl
1-pyrenyl AN-121 2-naphthyl phenyl AN-122 2-naphthyl 2-biphenyl
AN-123 2-naphthyl 3-biphenyl AN-124 2-naphthyl 4-biphenyl AN-125
2-naphthyl 2-p-terphenyl AN-126 9-phenanthryl 1-naphthyl AN-127
9-phenanthryl 2-naphthyl AN-128 9-phenanthryl 9-phenanthryl AN-129
9-phenanthryl 1-pyrenyl AN-130 9-phenanthryl phenyl AN-131
9-phenanthryl 2-biphenyl AN-132 9-phenanthryl 3-biphenyl AN-133
9-phenanthryl 4-biphenyl AN-134 9-phenanthryl 2-p-terphenyl AN-135
1-pyrenyl 1-naphthyl AN-136 1-pyrenyl 2-naphthyl AN-137 1-pyrenyl
9-phenanthryl AN-138 1-pyrenyl 1-pyrenyl AN-139 1-pyrenyl phenyl
AN-140 1-pyrenyl 2-biphenyl AN-141 1-pyrenyl 3-biphenyl AN-142
1-pyrenyl 4-biphenyl AN-143 1-pyrenyl 2-p-terphenyl AN-144 phenyl
1-naphthyl AN-145 phenyl 2-naphthyl AN-146 phenyl 9-phenanthryl
AN-147 phenyl 1-pyrenyl AN-148 phenyl phenyl AN-149 phenyl
2-biphenyl AN-150 phenyl 3-biphenyl AN-151 phenyl 4-biphenyl AN-152
phenyl 2-p-terphenyl AN-153 2-biphenyl 1-naphthyl AN-154 2-biphenyl
2-naphthyl AN-155 2-biphenyl 9-phenanthryl AN-156 2-biphenyl
1-pyrenyl AN-157 2-biphenyl phenyl AN-158 2-biphenyl 2-biphenyl
AN-159 2-biphenyl 3-biphenyl AN-160 2-biphenyl 4-biphenyl AN-161
2-biphenyl 2-p-terphenyl AN-162 3-biphenyl 1-naphthyl AN-163
3-biphenyl 2-naphthyl AN-164 3-biphenyl 9-phenanthryl AN-165
3-biphenyl 1-pyrenyl AN-166 3-biphenyl phenyl AN-167 3-biphenyl
2-biphenyl AN-168 3-biphenyl 3-biphenyl AN-169 3-biphenyl
4-biphenyl AN-170 3-biphenyl 2-p-terphenyl AN-171 4-biphenyl
1-naphthyl AN-172 4-biphenyl 2-naphthyl AN-173 4-biphenyl
9-phenanthryl AN-174 4-biphenyl 1-pyrenyl AN-175 4-biphenyl phenyl
AN-176 4-biphenyl 2-biphenyl AN-177 4-biphenyl 3-biphenyl AN-178
4-biphenyl 4-biphenyl AN-179 4-biphenyl 2-p-terphenyl
TABLE-US-00004 ##STR00006## Compound Ar.sup.1 Ar.sup.2 AN-180
1-naphthyl 1-naphthyl AN-181 1-naphthyl 2-naphthyl AN-182
1-naphthyl 9-phenanthryl AN-183 1-naphthyl 1-pyrenyl AN-184
1-naphthyl phenyl AN-185 1-naphthyl 2-biphenyl AN-186 1-naphthyl
3-biphenyl AN-187 1-naphthyl 4-biphenyl AN-188 2-naphthyl
1-naphthyl AN-189 2-naphthyl 2-naphthyl AN-190 2-naphthyl
9-phenanthryl AN-191 2-naphthyl 1-pyrenyl AN-192 2-naphthyl phenyl
AN-193 2-naphthyl 2-biphenyl AN-194 2-naphthyl 3-biphenyl AN-195
2-naphthyl 4-biphenyl AN-196 9-phenanthryl 1-naphthyl AN-197
9-phenanthryl 2-naphthyl AN-198 9-phenanthryl 9-phenanthryl AN-199
9-phenanthryl 1-pyrenyl AN-200 9-phenanthryl phenyl AN-201
9-phenanthryl 2-biphenyl AN-202 9-phenanthryl 3-biphenyl AN-203
9-phenanthryl 4-biphenyl AN-204 1-pyrenyl 1-naphthyl AN-205
1-pyrenyl 2-naphthyl AN-206 1-pyrenyl 9-phenanthryl AN-207
1-pyrenyl 1-pyrenyl AN-208 1-pyrenyl phenyl AN-209 1-pyrenyl
2-biphenyl AN-210 1-pyrenyl 3-biphenyl AN-211 1-pyrenyl 4-biphenyl
AN-212 phenyl 1-naphthyl AN-213 phenyl 2-naphthyl AN-214 phenyl
9-phenanthryl AN-215 phenyl 1-pyrenyl AN-216 phenyl phenyl AN-217
phenyl 2-biphenyl AN-218 phenyl 3-biphenyl AN-219 phenyl 4-biphenyl
AN-220 2-biphenyl 1-naphthyl AN-221 2-biphenyl 2-naphthyl AN-222
2-biphenyl 9-phenanthryl AN-223 2-biphenyl 1-pyrenyl AN-224
2-biphenyl phenyl AN-225 2-biphenyl 2-biphenyl AN-226 2-biphenyl
3-biphenyl AN-227 2-biphenyl 4-biphenyl AN-228 3-biphenyl
1-naphthyl AN-229 3-biphenyl 2-naphthyl AN-230 3-biphenyl
9-phenanthryl AN-231 3-biphenyl 1-pyrenyl AN-232 3-biphenyl phenyl
AN-233 3-biphenyl 2-biphenyl AN-234 3-biphenyl 3-biphenyl AN-235
3-biphenyl 4-biphenyl AN-236 4-biphenyl 1-naphthyl AN-237
4-biphenyl 2-naphthyl AN-238 4-biphenyl 9-phenanthryl AN-239
4-biphenyl 1-pyrenyl AN-240 4-biphenyl phenyl AN-241 4-biphenyl
2-biphenyl AN-242 4-biphenyl 3-biphenyl AN-243 4-biphenyl
4-biphenyl
TABLE-US-00005 ##STR00007## Compound Ar.sup.1 Ar.sup.2 AN-244
1-naphthyl 2-naphthyl AN-245 1-naphthyl 9-phenanthryl AN-246
1-naphthyl 1-pyrenyl AN-247 1-naphthyl phenyl AN-248 1-naphthyl
2-biphenyl AN-249 1-naphthyl 3-biphenyl AN-250 1-naphthyl
4-biphenyl AN-251 2-naphthyl 9-phenanthryl AN-252 2-naphthyl
1-pyrenyl AN-253 2-naphthyl phenyl AN-254 2-naphthyl 2-biphenyl
AN-255 2-naphthyl 3-biphenyl AN-256 2-naphthyl 4-biphenyl AN-257
9-phenanthryl 1-pyrenyl AN-258 9-phenanthryl phenyl AN-259
9-phenanthryl 2-biphenyl AN-260 9-phenanthryl 3-biphenyl AN-261
9-phenanthryl 4-biphenyl AN-262 1-pyrenyl phenyl AN-263 1-pyrenyl
2-biphenyl AN-264 1-pyrenyl 3-biphenyl AN-265 1-pyrenyl 4-biphenyl
AN-266 phenyl 2-biphenyl AN-267 phenyl 3-biphenyl AN-268 phenyl
4-biphenyl AN-269 2-biphenyl 3-biphenyl AN-270 2-biphenyl
4-biphenyl AN-271 3-biphenyl 4-biphenyl
TABLE-US-00006 ##STR00008## Compound Ar.sup.1 Ar.sup.2 AN-272
1-naphthyl 2-naphthyl AN-273 1-naphthyl 9-phenanthryl AN-274
1-naphthyl 1-pyrenyl AN-275 1-naphthyl phenyl AN-276 1-naphthyl
2-biphenyl AN-277 1-naphthyl 3-biphenyl AN-278 1-naphthyl
4-biphenyl AN-279 2-naphthyl 9-phenanthryl AN-280 2-naphthyl
1-pyrenyl AN-281 2-naphthyl phenyl AN-282 2-naphthyl 2-biphenyl
AN-283 2-naphthyl 3-biphenyl AN-284 2-naphthyl 4-biphenyl AN-285
9-phenanthryl 1-pyrenyl AN-286 9-phenanthryl phenyl AN-287
9-phenanthryl 2-biphenyl AN-288 9-phenanthryl 3-biphenyl AN-289
9-phenanthryl 4-biphenyl AN-290 1-pyrenyl phenyl AN-291 1-pyrenyl
2-biphenyl AN-292 1-pyrenyl 3-biphenyl AN-293 1-pyrenyl 4-biphenyl
AN-294 phenyl 2-biphenyl AN-295 phenyl 3-biphenyl AN-296 phenyl
4-biphenyl AN-297 2-biphenyl 3-biphenyl AN-298 2-biphenyl
4-biphenyl AN-299 3-biphenyl 4-biphenyl
TABLE-US-00007 ##STR00009## Compound Ar.sup.1 Ar.sup.2 AN-300
1-naphthyl 1-naphthyl AN-301 1-naphthyl 2-naphthyl AN-302
1-naphthyl 9-phenanthryl AN-303 1-naphthyl 1-pyrenyl AN-304
1-naphthyl phenyl AN-305 1-naphthyl 2-biphenyl AN-306 1-naphthyl
3-biphenyl AN-307 1-naphthyl 4-biphenyl AN-308 1-naphthyl
2-p-terphenyl AN-309 2-naphthyl 1-naphthyl AN-310 2-naphthyl
2-naphthyl AN-311 2-naphthyl 9-phenanthryl AN-312 2-naphthyl
1-pyrenyl AN-313 2-naphthyl phenyl AN-314 2-naphthyl 2-biphenyl
AN-315 2-naphthyl 3-biphenyl AN-316 2-naphthyl 4-biphenyl AN-317
2-naphthyl 2-p-terphenyl
TABLE-US-00008 ##STR00010## Compound Ar.sup.1 Ar.sup.2 AN-318
1-naphthyl 1-naphthyl AN-319 1-naphthyl 2-naphthyl AN-320
1-naphthyl 9-phenanthryl AN-321 1-naphthyl 1-pyrenyl AN-322
1-naphthyl phenyl AN-323 1-naphthyl 2-biphenyl AN-324 1-naphthyl
3-biphenyl AN-325 1-naphthyl 4-biphenyl AN-326 1-naphthyl
2-p-terphenyl AN-327 2-naphthyl 1-naphthyl AN-328 2-naphthyl
2-naphthyl AN-329 2-naphthyl 9-phenanthryl AN-330 2-naphthyl
1-pyrenyl AN-331 2-naphthyl phenyl AN-332 2-naphthyl 2-biphenyl
AN-333 2-naphthyl 3-biphenyl AN-334 2-naphthyl 4-biphenyl AN-335
2-naphthyl 2-p-terphenyl
TABLE-US-00009 ##STR00011## Compound Ar.sup.1 Ar.sup.2 AN-336
1-naphthyl 1-naphthyl AN-337 1-naphthyl 2-naphthyl AN-338
1-naphthyl 9-phenanthryl AN-339 1-naphthyl 1-pyrenyl AN-340
1-naphthyl phenyl AN-341 1-naphthyl 2-biphenyl AN-342 1-naphthyl
3-biphenyl AN-343 1-naphthyl 4-biphenyl AN-344 1-naphthyl
2-p-terphenyl AN-345 2-naphthyl 1-naphthyl AN-346 2-naphthyl
2-naphthyl AN-347 2-naphthyl 9-phenanthryl AN-348 2-naphthyl
1-pyrenyl AN-349 2-naphthyl phenyl AN-350 2-naphthyl 2-biphenyl
AN-351 2-naphthyl 3-biphenyl AN-352 2-naphthyl 4-biphenyl AN-353
2-naphthyl 2-p-terphenyl
TABLE-US-00010 ##STR00012## Compound Ar.sup.1 Ar.sup.2 AN-354
1-naphthyl 1-naphthyl AN-355 1-naphthyl 2-naphthyl AN-356
1-naphthyl 9-phenanthryl AN-357 1-naphthyl 1-pyrenyl AN-358
1-naphthyl phenyl AN-359 1-naphthyl 2-biphenyl AN-360 1-naphthyl
3-biphenyl AN-361 1-naphthyl 4-biphenyl AN-362 1-naphthyl
2-p-terphenyl AN-363 2-naphthyl 1-naphthyl AN-364 2-naphthyl
2-naphthyl AN-365 2-naphthyl 9-phenanthryl AN-366 2-naphthyl
1-pyrenyl AN-367 2-naphthyl phenyl AN-368 2-naphthyl 2-biphenyl
AN-369 2-naphthyl 3-biphenyl AN-370 2-naphthyl 4-biphenyl AN-371
2-naphthyl 2-p-terphenyl
TABLE-US-00011 ##STR00013## Compound Ar.sup.1 Ar.sup.2 AN-372
1-naphthyl 1-naphthyl AN-373 1-naphthyl 2-naphthyl AN-374
1-naphthyl 9-phenanthryl AN-375 1-naphthyl 1-pyrenyl AN-376
1-naphthyl phenyl AN-377 1-naphthyl 2-biphenyl AN-378 1-naphthyl
3-biphenyl AN-379 1-naphthyl 4-biphenyl AN-380 1-naphthyl
2-p-terphenyl AN-381 2-naphthyl 1-naphthyl AN-382 2-naphthyl
2-naphthyl AN-383 2-naphthyl 9-phenanthryl AN-384 2-naphthyl
1-pyrenyl AN-385 2-naphthyl phenyl AN-386 2-naphthyl 2-biphenyl
AN-387 2-naphthyl 3-biphenyl AN-388 2-naphthyl 4-biphenyl AN-389
2-naphthyl 2-p-terphenyl
##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018##
##STR00019## ##STR00020## ##STR00021##
[0043] The asymmetric monoanthracene derivative of the present
invention represented by Formula (1) can be synthesized by suitably
combining Suzuki coupling reaction, halogenation reaction and
boration reaction which are publicly known methods using
halogenated aryl derivatives and anthrylboronic acid derivative as
starting materials. The synthetic scheme thereof shall be shown
below.
##STR00022##
[0044] A lot of reports (Chem. Rev., Vol. 95, No. 7, 2457 (1995)
and the like) has so far been made on the Suzuki coupling reaction,
and it can be carried out on reaction conditions described in these
reports.
[0045] Usually, the reaction is carried out at atmospheric pressure
under inert atmosphere of nitrogen, argon and helium, and it can be
carried out as well, if necessary, under a pressurized condition.
The reaction temperature falls in a range of 15 to 300.degree. C.,
particularly preferably 30 to 200.degree. C.
[0046] Capable of being used as the reaction solvent alone or in a
mixture are water, aromatic hydrocarbons such as benzene, toluene
and xylene, ethers such as 1,2-dimethoxyethane, diethyl ether,
methyl t-butyl ether, tetrahydrofuran and dioxane, saturated
hydrocarbons such as pentane, hexane, heptane, octane and
cyclohexane, halides such as dichloromethane, chloroform, carbon
tetrachloride, 1,2-dichloroethane and 1,1,1-trichloroethane,
nitriles such as acetonitrile and benzonitrile, esters such as
ethyl acetate, methyl acetate and butyl acetate and amides such as
N,N-dimethylformamide, N,N-dimethylacetamide and
N-methylpyrrolidone. Among them, toluene, 1,2-dimethoxyethane,
dioxane and water are preferred. A use amount of the solvent is
usually 3 to 50 weight times, preferably 4 to 20 weight times based
on arylboronic acid or a derivative thereof.
[0047] The base used for the reaction includes, for example, sodium
carbonate, potassium carbonate, sodium hydroxide, potassium
hydroxide, sodium hydrogencarbonate, potassium hydrogencarbonate,
magnesium carbonate, lithium carbonate, potassium fluoride, cesium
fluoride, cesium chloride, cesium bromide, cesium carbonate,
potassium phosphate, sodium methoxide, potassium t-butoxide, sodium
t-butoxide and lithium t-butoxide, and it is preferably sodium
carbonate. A use amount of the above bases is usually 0.7 to 10
mole equivalent, preferably 0.9 to 6 mole equivalent based on
arylboronic acid or a derivative thereof.
[0048] The catalyst used for the reaction includes, for example,
palladium catalysts such as tetrakis(triphenylphosphine)palladium,
dichlorobis(triphenylphosphine)palladium,
dichloro[bis(diphenylphosphino)ethane]palladium,
dichloro[bis(diphenylphosphino)propane]palladium,
dichloro[bis(diphenylphosphino)butane]palladium and
dichloro[bis(diphenylphosphino)ferrocene]palladium and nickel
catalysts such as tetrakis(triphenylphosphine)nickel,
dichlorobis(triphenylphosphine)nickel,
dichloro[bis(diphenylphosphino)ethane]nickel,
dichloro[bis(diphenylphosphino)propane]nickel,
dichloro[bis(diphenylphosphino)butane]nickel and
dichloro[bis(diphenylphosphino)ferrocene]nickel, and it is
preferably tetrakis(triphenylphosphine)palladium. A use amount of
the above catalysts is usually 0.001 to 1 mole equivalent,
preferably 0.01 to 0.1 mole equivalent based on the halogenated
anthracene derivative.
[0049] Halogen of the halogenated anthracene derivative includes,
for example, an iodine atom, a bromine atom and a chlorine atom,
and it is preferably an iodine atom and a bromine atom.
[0050] A halogenating agent in the halogenation reaction shall not
specifically be restricted, and N-halogenated succinimide is
suitably used. A use amount of the halogenating agent is usually
0.8 to 10 mole equivalent, preferably 1 to 5 mole equivalent based
on the anthracene derivative.
[0051] Usually, the reaction is carried out in an inert solvent
under an inert atmosphere of nitrogen, argon and helium. The inert
solvent includes, for example, N,N-dimethylformamide,
N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide,
carbon tetrachloride, chlorobenzene, dichlorobenzene, nitrobenzene,
toluene, xylene, methyl cellosolve, ethyl cellosolve and water, and
it is preferably N,N-dimethylformamide and N-methylpyrrolidone. A
use amount of the solvent is usually 3 to 50 weight times,
preferably 5 to 20 weight times based on the anthracene derivative.
The reaction is carried out at a temperature of usually 0 to
200.degree. C., preferably 20 to 120.degree. C.
[0052] The boration reaction can be carried out by known methods
(Experimental Chemistry Course Fourth Edition, vol. 24, p. 61 to
90, edited by Japan Chemical Society, J. Org. Chem., Vol. 70, 7508
(1995) and the like). In the case of, for example, the reaction via
lithiation of halogenated anthracene derivatives or Grignard
reaction, it is carried out usually under an inert atmosphere of
nitrogen, argon and helium, and an inert solvent is used as the
reaction solvent. Capable of being used as the reaction solvent
alone or in a mixture are, for example, saturated hydrocarbons such
as pentane, hexane, heptane, octane and cyclohexane, ethers such as
1,2-dimethoxyethane, diethyl ether, methyl t-butyl ether,
tetrahydrofuran and dioxane and aromatic hydrocarbons such as
benzene, toluene and xylene, and it is preferably diethyl ether and
toluene. A use amount of the solvent is usually 3 to 50 weight
times, preferably 4 to 20 weight times based on the halogenated
anthracene derivative.
[0053] Capable of being used as the lithiation agent are, for
example, alkyl metal reagents such as n-butyllithium,
t-butyllithium, phenyllithium and methyllithium and amide bases
such as lithium diisopropylamide and lithium
bistrimethylsilylamide, and it is preferably n-butyllithium. The
Grignard reagent can be prepared by reacting the halogenated
anthracene derivative with metallic magnesium. Capable of being
used as trialkyl borate which is the boration agent are, for
example, trimethyl borate, triethyl borate, triisopropyl borate and
tributyl borate, and it is preferably trimethyl borate and
triisopropyl borate.
[0054] The use amounts of the lithiation agent and metallic
magnesium each are usually 1 to 10 mole equivalent, preferably 1 to
2 mole equivalent based on the halogenated anthracene derivative. A
use amount of trialkyl borate is usually 1 to 10 mole equivalent,
preferably 1 to 5 mole equivalent based on the halogenated
anthracene derivative. The reaction temperature is usually -100 to
50.degree. C., preferably -75 to 10'C.
[0055] The organic EL device of the present invention is an organic
EL device in which an organic thin film layer comprising a single
layer or plural layers including a luminescent layer is interposed
between a cathode and an anode, wherein at least one of the above
thin film layers contains the asymmetric monoanthracene derivative
represented by Formula (1) described above in the form of a single
component or a mixed component.
[0056] In the organic EL device of the present invention, the
luminescent layer described above preferably contains the
asymmetric monoanthracene derivative represented by Formula (1) as
a principal component.
[0057] Further, in the organic EL device of the present invention,
the luminescent layer described above preferably further contains
an arylamine compound and/or a styrylamine compound.
[0058] The styrylamine compound is preferably a compound
represented by the following Formula (A):
##STR00023##
(wherein Ar.sup.2 is a group selected from a phenyl group, a
biphenyl group, a terphenyl group, a stilbene group and a
distyrylaryl group; Ar.sup.3 and Ar.sup.4 each are a hydrogen atom
or an aromatic hydrocarbon ring group having 6 to 20 carbon atoms,
and Ar.sup.2, Ar.sup.3 and Ar.sup.4 may be substituted; p is an
integer of 1 to 4; and more preferably, at least one of Ar.sup.3
and Ar.sup.4 is substituted with a styryl group).
[0059] In this regard, the aromatic hydrocarbon ring group having 6
to 20 carbon atoms includes phenyl, naphthyl, anthranyl,
phenanthryl and terphenyl.
[0060] The arylamine compound is preferably a compound represented
by the following Formula (B):
##STR00024##
(wherein Ar.sup.y to Ar.sup.7 are a substituted or non-substituted
aryl group having 5 to 40 nuclear carbon atoms; and q is an integer
of 1 to 4).
[0061] In this regard, the aryl group having 5 to 40 nuclear carbon
atoms includes, for example, phenyl, naphthyl, anthranyl,
phenanthryl, pyrenyl, coronyl, biphenyl, terphenyl, pyrrolyl,
furanyl, thiophenyl, benzothiophenyl, oxadiazolyl,
diphenylanthranyl, indolyl, carbazolyl, pyridyl, benzoquinolyl,
fluoroanthenyl, acenaphthofluoranthenyl, stilbene, perylenyl,
chrysenyl, picenyl, triphenylenyl, rubicenyl, benzoanthracenyl,
phenylanthranyl, bisanthracenyl and aryl groups represented by the
following Formulas (C) and (D):
##STR00025##
(in Formula (C), r is an integer of 1 to 3).
[0062] Preferred substituents of the aryl group described above
include an alkyl group having 1 to 6 carbon atoms (ethyl, methyl,
i-propyl, n-propyl, s-butyl, t-butyl, pentyl, hexyl, cyclopentyl
and cyclohexyl), an alkoxy group having 1 to 6 carbon atoms
(ethoxy, methoxy, i-propoxy, n-propoxy, s-butoxy, t-butoxy,
pentoxy, hexyloxy, cyclopentoxy and cyclohexyloxy), an aryl group
having 5 to 40 nuclear carbon atoms, an amino group substituted
with an aryl group having 5 to 40 nuclear carbon atoms, an ester
group having an aryl group having 5 to 40 nuclear carbon atoms, an
ester group having an alkyl group having 1 to 6 carbon atoms, a
cyano group, a nitro group and a halogen atom.
[0063] Ar.sup.5 is particularly preferably naphthyl, anthranyl,
chrysenyl, pyrenyl or the aryl group represented by Formula (D),
which are substituted or non-substituted respectively.
[0064] The material for the organic EL device of the present
invention comprises the asymmetric monoanthracene derivative
represented by Formula (1) described above, and it is preferably a
luminescent material. Further, it is preferably a host
material.
[0065] The device structure of the organic EL device of the present
invention shall be explained below.
[0066] The typical examples of the device structure of the organic
EL device of the present invention include structure such as:
[0067] (1) anode/luminescent layer/cathode, [0068] (2) anode/hole
injecting layer/luminescent layer/cathode, [0069] (3)
anode/luminescent layer/electron injecting layer/cathode, [0070]
(4) anode/hole injecting layer/luminescent layer/electron injecting
layer/cathode, [0071] (5) anode/organic semiconductor
layer/luminescent layer/cathode, [0072] (6) anode/organic
semiconductor layer/electron barrier layer/luminescent
layer/cathode, [0073] (7) anode/organic semiconductor
layer/luminescent layer/adhesion improving layer/cathode, [0074]
(8) anode/hole injecting layer/hole transporting layer/luminescent
layer/electron injecting layer/cathode [0075] (9) anode/insulating
layer/luminescent layer/insulating layer/cathode, [0076] (10)
anode/inorganic semiconductor layer/insulating layer/luminescent
layer/insulating layer/cathode [0077] (11) anode/organic
semiconductor layer/insulating, layer/luminescent layer/insulating
layer/cathode, [0078] (12) anode/insulating layer/hole injecting
layer/hole transporting layer/luminescent layer/insulating
layer/cathode and [0079] (13) anode/insulating layer/hole injecting
layer/hole transporting layer/luminescent layer/electron injecting
layer/cathode
[0080] Among them, usually the structure of (8) is preferably used,
but it shall not be restricted to them.
[0081] The above organic EL device is usually prepared on a light
transmitting substrate. This light transmitting substrate is a
substrate supporting the organic EL device, and as far as a light
transmitting property thereof is concerned, a substrate in which
light in a visible region of 400 to 700 nm has a transmission
factor of 50% or more is preferred, and a flat substrate is
preferably used.
[0082] For example, a glass plate and a synthetic resin plate are
preferably used as the above light transmitting substrate. The
glass plate includes plates molded particularly by soda lime glass,
barium.strontium-containing glass, lead glass, aluminosilicate
glass, borosilicate glass, barium borosilicate glass and quartz.
The synthetic resin plate includes plates of polycarbonate resins,
acryl resins, polyethylene terephthalate resins, polyether sulfide
resins and polysulfone resins.
[0083] Next, the anode assumes a role to inject a hole into the
hole transporting layer or the luminescent layer, and it is
effective to provide the anode with a work function of 4.5 eV or
more. The specific examples of a material for the anode used in the
present invention include indium tin oxide alloy (ITO), tin oxide
(NESA), gold, silver, platinum and copper. The cathode is
preferably a material having a small work function for the purpose
of injecting an electron into the electron transporting layer or
the luminescent layer.
[0084] The anode can be prepared by forming a thin film of the
above electrode substances by a method such as a deposition method
and a sputtering method.
[0085] When light emitted from the luminescent layer is taken out
from the anode, a transmission factor of the anode based on light
emitted is preferably larger than 10%. A sheet resistance of the
anode is preferably several hundred .OMEGA./.quadrature. or less. A
film thickness of the anode is selected, though depending on the
material, in a range of usually 10 nm to 1 .mu.m, preferably 10 to
200 nm.
[0086] In the organic EL device of the present invention, the
luminescent layer has:
(1) an injecting function: a function in which a hole can be
injected from an anode or a hole injecting layer in applying an
electric field and in which an electron can be injected from a
cathode or an electron injecting layer, (2) a transporting
function: a function in which a charge injected (electron and hole)
is migrated by virtue of a force of an electric field and (3) a
luminescent function: a function in which a field for recombination
of an electron and a hole is provided and in which this is
connected to luminescence.
[0087] A publicly known method such as, for example, a deposition
method, a spin coating method and an LB method can be applied as a
method for forming the above luminescent layer. In particular, the
luminescent layer is preferably a molecular deposit film. In this
case, the molecular deposit film means a thin film formed by
depositing a material compound staying in a gas phase state and a
film formed by solidifying a material compound staying in a
solution state or a liquid phase state, and usually the above
molecular deposit film can be distinguished from a thin film
(molecular accumulation film) formed by the LB method by a
difference in an aggregation structure and a higher order structure
and a functional difference originating in it.
[0088] Further, as disclosed in Japanese Patent Application
Laid-Open No. 51781/1982, the luminescent layer can be formed as
well by dissolving a binding agent such as a resin and the material
compound in a solvent to prepare a solution and then coating the
solution by a spin coating method to form a thin film.
[0089] Other publicly known luminescent materials other than the
luminescent material of the present invention may be added, if
necessary, to the luminescent layer as long as the object of the
present invention is not damaged. Further, a luminescent layer
containing a different publicly known luminescent material may be
laminated on the luminescent layer containing the luminescent
material of the present invention.
[0090] Next, the hole injecting and transporting layers are layers
for assisting injection of a hole into the luminescent layer to
transport it to the luminescent region, and they have a large hole
mobility and have a small ionization energy of usually 5.5 eV or
less. A material which transports a hole to the luminescent layer
by a lower electric field strength is preferred as the above hole
injecting and transporting layers, and more preferred is a material
in which a mobility of a hole is at least 10.sup.-6
cm.sup.2/Vsecond in applying an electric field of, for example,
10.sup.4 to 10.sup.6 V/cm. Capable of being used as the above
material are optional materials selected from materials which have
so far conventionally been used as charge transporting materials of
holes in photoconductive materials and publicly known materials
which are used for a hole injecting layer in an organic EL
device.
[0091] The specific examples thereof include, for example, triazole
derivatives (refer to U.S. Pat. No. 3,112,197), oxadiazole
derivatives (refer to U.S. Pat. No. 3,189,447), imidazole
derivatives (refer to Japanese Patent Publication No. 16096/1962),
polyarylalkane derivatives (refer to U.S. Pat. No. 3,615,402, ditto
3,820,989 and ditto 3,542,544, Japanese Patent Publication No.
555/1970 and ditto 10983/1976 and Japanese Patent Application
Laid-Open No. 93224/1976, ditto 17105/1980, ditto 4148/1981, ditto
10866/1980, ditto 156953/1980 and ditto 36656/1981), pyrazoline
derivatives and pyrazolone derivatives (refer to U.S. Pat. No.
3,180,729 and ditto 4,278,746 and Japanese Patent Application
Laid-Open No. 88064/1980, ditto 88065/1980, ditto 105537/1974,
ditto 51086/1980, ditto 80051/1981, ditto 88141/1981, ditto
45545/1982, ditto 112637/1979 and ditto 74546/1980),
phenylenediamine derivatives (refer to U.S. Pat. No. 3,615,404,
Japanese Patent Publication No. 10105/1976, ditto 3712/1971 and
ditto 25336/1972 and Japanese Patent Application Laid-Open No.
53435/1979, ditto 110536/1979 and ditto 119925/1979), arylamine
derivatives (refer to U.S. Pat. No. 3,567,450, ditto 3,180,703,
ditto 3,240,597, ditto 3,658,520, ditto 4,232,103, ditto 4,175,961
and ditto 4,012,376, Japanese Patent Publication No. 35702/1974 and
ditto 27577/1964, Japanese Patent Application Laid-Open No.
144250/1980, ditto 119132/1981 and ditto 22437/1981 and German
Patent 1,110,518), amino-substituted chalcone derivatives (refer to
U.S. Pat. No. 3,526,501), oxazole derivatives (disclosed in U.S.
Pat. No. 3,257,203), styrylanthracene derivatives (refer to
Japanese Patent Application Laid-Open No. 46234/1981), fluorenone
derivatives (refer to Japanese Patent Application Laid-Open No.
110837/1979), hydrazone derivatives (refer to U.S. Pat. No.
3,717,462, Japanese Patent Application Laid-Open No. 59143/1979,
ditto 52063/1980, ditto 52064/1980, ditto 46760/1980, ditto
85495/1980, ditto 11350/1982 and ditto 148749/1982 and Japanese
Patent Application Laid-Open No. 311591/1990), stilbene derivatives
(Japanese Patent Application Laid-Open No. 210363/1986, ditto
228451/1986, ditto 14642/1986, ditto 72255/1986, ditto 47646/1987,
ditto 36674/1987, ditto 10652/1987, ditto 30255/1987, ditto
93455/1985, ditto 94462/1985, ditto 174749/1985 and ditto
175052/1985), silazane derivatives (refer to U.S. Pat. No.
4,950,950), polysilane base (refer to Japanese Patent Application
Laid-Open No. 204996/1990), aniline base copolymers (refer to
Japanese Patent Application Laid-Open No. 282263/1990) and
electroconductive high molecular oligomers (particularly thiophene
oligomers) disclosed in Japanese Patent Application Laid-Open No.
211399/1989.
[0092] The compounds described above can be used as the material
for the hole injecting layer, and preferably used are porphyrin
compounds (disclosed in Japanese Patent Application Laid-Open No.
2956965/1988), aromatic tertiary amine compounds and styrylamine
compounds (refer to U.S. Pat. No. 4,127,412 and Japanese Patent
Application Laid-Open No. 27033/1978, ditto 58445/1979, ditto
149634/1979, ditto 64299/1979, ditto 79450/1980, ditto 144250/1980,
ditto 119132/1981, ditto 295558/1986, ditto 98353/1986 and ditto
295695/1988), and the aromatic tertiary amine compounds are
particularly preferably used.
[0093] Further, capable of being given are compounds having two
condensed aromatic rings in a molecule described in U.S. Pat. No.
5,061,569, for example,
4,4'-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (hereinafter
abbreviated as NPD) and
4,4',4''-tris(N-(3-methylphenyl)-N-phenylamino)triphenyl
(hereinafter abbreviated as MTDATA) in which three triphenylamine
units are combined in the form of a star burst type disclosed in
Japanese Patent Application Laid-Open No. 308688/1992.
[0094] Further, inorganic compounds such as p type Si, p type SiC
and the like in addition to the aromatic dimethylidene base
compounds described above shown as the material for the luminescent
layer can also be used as the material for the hole injecting
layer.
[0095] The hole injecting and transporting layers can be formed by
making a thin film from the compound described above by a publicly
known method such as, for example, a vacuum deposition method, a
spin coating method, a casting method and an LB method. A film
thickness of the hole injecting and transporting layers shall not
specifically be restricted, and it is usually 5 nm to 5 .mu.m. The
above hole injecting and transporting layers may be constituted
from a single layer comprising at least one of the materials
described above as long as the compound of the present invention is
contained in the hole transporting zone, and hole injecting and
transporting layers comprising compounds which are different from
those used in the hole injecting and transporting layers described
above may be laminated thereon.
[0096] Further, an organic semiconductor layer is a layer for
assisting injection of a hole or injection of an electron into the
luminescent layer, and the layer having an electric conductivity of
10.sup.-10 S/cm or more is suited. Capable being used as a material
for the above organic semiconductor layer are conductive oligomers
such as thiophene-containing oligomers and arylamine-containing
oligomers disclosed in Japanese Patent Application Laid-Open No.
193191/1996 and conductive dendrimers such as arylamine-containing
dendrimers.
[0097] Next, the electron injecting and transporting layers are
layers for assisting injection of an electron into the luminescent
layer to transport it to the luminescent region, and they have a
large electron mobility. Also, the adhesion improving layer is a
layer comprising particularly a material having a good adhesive
property with the cathode in the above electron injecting layer.
The metal complexes of 8-hydroxyquinoline or the derivatives
thereof and oxadiazole derivatives are suited as a material used
for the electron injecting layer. The specific examples of the
above metal complexes of 8-hydroxyquinoline or the derivatives
thereof include metal chelate oxynoid compounds containing chelates
of oxine (in general, 8-quinolinol or 8-hydroxyquinoline), and, for
example, tris(8-quinolinol)aluminum can be used as the electron
injecting material.
[0098] On the other hand, the oxadiazole derivative includes
electron transmitting compounds represented by the following
formulas:
##STR00026##
wherein Ar.sup.1', Ar.sup.2', Ar.sup.3', Ar.sup.5', Ar.sup.6' and
Ar.sup.9' each represent a substituted or non-substituted aryl
group, and they may be the same as or different from each other;
Ar.sup.4', Ar.sup.7' and Ar.sup.8' each represent a substituted or
non-substituted arylene group, and they may be the same as or
different from each other.
[0099] In this connection, the aryl group includes phenyl,
biphenyl, anthranyl, perylenyl and pyrenyl. Also, the arylene group
includes phenylene, naphthylene, biphenylene, anthranylene,
perylenylene and pyrenylene. The substituents therefor include an
alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1
to 10 carbon atoms and a cyano group. The above electron
transmitting compounds have preferably a thin film-forming
property.
[0100] The following compounds can be given as the specific
examples of the electron transmitting compounds described
above:
##STR00027##
[0101] The preferred mode of the organic EL device of the present
invention includes a device containing a reducing dopant in the
region which transports an electron or an interfacial region
between the cathode and the organic layer. In this case, the
reducing dopant is defined by a substance which can reduce an
electron transporting compound. Accordingly, various compounds can
be used as long as they have a reducing property of some extent,
and capable of being suitably used is at least one substance
selected from the group consisting of, for example, alkaline
metals, alkaline earth metals, rare earth metals, oxides of
alkaline metals, halides of alkaline metals, oxides of alkaline
earth metals, halides of alkaline earth metals, oxides of rare
earth metals or halides of rare earth metals, organic complexes of
alkaline metals, organic complexes of alkaline earth metals and
organic complexes of rare earth metals.
[0102] To be more specific, the preferred reducing dopant includes
at least one alkaline metal selected from the group consisting of
Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work
function: 2.16 eV) and Cs (work function: 1.95 eV) and at least one
alkaline earth metal selected from the group consisting of Ca (work
function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV) and Ba (work
function: 2.52 eV), and the compounds having a work function of 2.9
eV or less are particularly preferred. Among them, the more
preferred reducing dopant is at least one alkaline metal selected
from the group consisting of K, Rb and Cs, and it is more
preferably Rb or Cs. It is most preferably Cs. The above alkaline
metals have a particularly high reducing ability, and addition of a
relatively small amount thereof to the electron injecting zone
makes it possible to raise a light emitting luminance and extend
the life thereof in the organic EL device. The combination of two
or more kinds of the above alkaline metals is preferred as the
reducing dopant having a work function of 2.9 eV or less, and
particularly preferred is the combination containing Cs, for
example, Cs and Na, Cs and K, Cs and Rb or Cs, Na and K. Containing
Cs in combination makes it possible to efficiently exhibit the
reducing ability, and addition thereof to the electron injecting
zone makes it possible to raise a light emitting luminance and
extend the life thereof in the organic EL element.
[0103] In the present invention, an electron injecting layer
constituted from an insulator and a semiconductor may further be
provided between the cathode and the organic layer. In this case,
an electric current can effectively be prevented from leaking to
raise the electron injecting property. Preferably used as the above
insulator is at least one metal compound selected from the group
consisting of alkaline metal chalcogenides, alkaline earth metal
chalcogenides, halides of alkaline metals and halides of alkaline
earth metals. If the electron injecting layer is constituted from
the above alkaline metal chalcogenides, it is preferred from the
viewpoint that the electron injecting property can further be
enhanced. To be specific, the preferred alkaline metal
chalcogenides include, for example, Li.sub.2O, LiO, Na.sub.2S,
Na.sub.2Se and NaO, and the preferred alkaline earth metal
chalcogenides include, for example, CaO, BaO, SrO, BeO, BaS and
CaSe. Also, the preferred halides of alkaline metals include, for
example, LiF, NaF, KF, LiCl, KCl and NaCl. Further, the preferred
halides of alkaline earth metals include, for example, fluorides
such as CaF.sub.2, BaF.sub.2, SrF.sub.2, MgF.sub.2 and BeF.sub.2
and halides other than the fluorides.
[0104] The semiconductor constituting the electron transporting
layer includes one kind alone of oxides, nitrides or nitride oxides
containing at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li,
Na, Cd, Mg, Si, Ta, Sb and Zn or combinations of two or more kinds
thereof. The inorganic compound constituting the electron
transporting layer is preferably a crystallite or amorphous
insulating thin film. If the electron transporting layer is
constituted from the above insulating thin film, the more
homogeneous thin film is formed, and therefore picture element
defects such as dark spots can be reduced. The above inorganic
compound includes the alkaline metal chalcogenides, the alkaline
earth metal chalcogenides, the halides of alkaline metals and the
halides of alkaline earth metals each described above.
[0105] Next, electrodes using metals, alloys, electroconductive
compounds and mixtures thereof each having a small work function (4
eV or less) for the electrode material are used as the cathode. The
specific examples of the above electrode material include sodium,
sodium-potassium alloys, magnesium, lithium, magnesium silver
alloys, aluminum/aluminum oxide, Al/Li.sub.2O, Al/LiO.sub.2,
Al/LiF, aluminum.lithium alloys, indium and rare earth metals.
[0106] The above cathode can be prepared by forming a thin film
from the above electrode materials by a method such as deposition
and sputtering.
[0107] In this respect, when light emitted from the luminescent
layer is taken out from the cathode, a transmission factor of the
cathode based on light emitted is preferably larger than 10%. A
sheet resistance of the cathode is preferably several hundred
.OMEGA./.quadrature. or less, and a film thickness thereof is
usually 10 nm to 1 .mu.m, preferably 50 to 200 nm.
[0108] In general, in an organic EL device, an electric field is
applied to a ultrathin film, and therefore it is liable to cause
picture element defects by leak and short. In order to prevent
this, an insulating thin film layer may be interposed between a
pair of the electrodes.
[0109] A material used for the insulating layer includes, for
example, aluminum oxide, lithium fluoride, lithium oxide, cesium
fluoride, cesium oxide, magnesium oxide, magnesium fluoride,
calcium oxide, calcium fluoride, aluminum nitride, titanium oxide,
silicon oxide, germanium oxide, silicon nitride, boron nitride,
molybdenum oxide, ruthenium oxide and vanadium oxide, and mixtures
and laminates thereof may be used.
[0110] Next, in respect to a process for preparing the organic EL
device of the present invention, the anode, the luminescent layer,
if necessary, the hole injecting layer and, if necessary, the
electron injecting layer are formed according to the materials and
the methods each described above, and finally the cathode is
formed. Also, the organic EL device can be prepared as well from
the cathode to the anode in an order which is reverse to what was
described above.
[0111] A preparation example of the organic EL device having a
structure in which an anode/a hole injecting layer/a luminescent
layer/an electron injecting layer/a cathode are provided in order
on a light transmitting substrate shall be explained below.
[0112] First, a thin film comprising an anode material is formed on
a suitable light transmitting substrate by a deposition method or a
sputtering method so that a film thickness falls in a range of 1
.mu.m or less, preferably 10 to 200 nm, whereby an anode is
prepared. Next, a hole injecting layer is provided on the above
anode. The hole injecting layer can be formed, as described above,
by a method such as a vacuum deposition method, a spin coating
method, a casting method and an LB method, and it is preferably
formed by the vacuum deposition method from the viewpoints that the
homogeneous film is liable to be obtained and that pinholes are
less liable to be produced. When forming the hole injecting layer
by the vacuum deposition method, the depositing conditions thereof
are varied according to the compounds used (a material for the hole
injecting layer), the crystal structure of the intended hole
injecting layer and the recombination structure, and in general,
they are suitably selected preferably in the ranges of a depositing
source temperature of 50 to 450.degree. C., a vacuum degree of
10.sup.-7 to 10.sup.-3 torr, a depositing speed of 0.01 to 50
nm/second, a substrate temperature of -50 to 300.degree. C. and a
film thickness of 5 nm to 5 .mu.m.
[0113] Next, a luminescent layer is provided on the above hole
injecting layer. This luminescent layer can be formed by making a
thin film from the luminescent material according to the present
invention by a method such as a vacuum deposition method, a
sputtering method, a spin coating method and a casting method, and
it is preferably formed by the vacuum deposition method from the
viewpoints that the homogeneous film is liable to be obtained and
that pinholes are less liable to be produced. When forming the
luminescent layer by the vacuum deposition method, the depositing
conditions thereof are varied according to the compounds used, and
in general, they can be selected from the same condition ranges as
in forming the hole injecting layer. The layer thickness falls
preferably in a range of 10 to 90 nm.
[0114] Next, an electron injecting layer is provided on the above
luminescent layer. Also in this case, it is preferably formed by
the vacuum deposition method as is the case with the hole injecting
layer and the luminescent layer since the homogeneous film has to
be obtained. The depositing conditions thereof can be selected from
the same condition ranges as in the hole injecting layer and the
luminescent layer.
[0115] Lastly, a cathode is laminated, whereby an organic EL device
can be obtained. The cathode is constituted from metal, and
therefore the deposition method and the sputtering method can be
used. However, the vacuum deposition method is preferred in order
to protect the organic substance layer of the base from being
damaged in making the film.
[0116] The above organic EL device is preferably prepared serially
from the anode up to the cathode in one vacuuming.
[0117] The forming methods of the respective layers in the organic
EL device of the present invention shall not specifically be
restricted, and the forming methods carried out by the vacuum
deposition method and the spin coating method which have so far
publicly been known can be used. The organic thin film containing
the compound represented by Formula (1) described above which is
used for the organic EL device of the present invention can be
formed by a publicly known method carried out by a coating method
such as a vacuum deposition method, a molecular beam evaporation
method (MBE method), a dipping method using a solution prepared by
dissolving the compound in a solvent, a spin coating method, a
casting method, a bar coating method and a roll coating method.
[0118] The film thicknesses of the respective organic layers in the
organic EL device of the present invention shall not specifically
be restricted, and it falls preferably in a range of usually
several nm to 1 .mu.m in order to prevent defects such as pinholes
and improve the efficiency.
[0119] When applying a direct voltage to the organic EL device,
luminance can be observed by applying a voltage of 5 to 40 V
setting a polarity of the anode to plus and that of the cathode to
minus. An electric current does not flow by applying a voltage with
the reverse polarities, and luminance is not caused at all.
Further, when applying an AC voltage, uniform luminance can be
observed only when the anode has a polarity of plus and the cathode
has a polarity of minus. The waveform of an alternating current
applied may be optional.
EXAMPLES
[0120] Next, the present invention shall be explained in further
details with reference to examples, but the present invention shall
by no means be restricted by these examples.
Synthetic Example 1 synthesis of 2-(4-bromophenyl)naphthalene
[0121] 4-Bromoiodobenzene 25.0 g, 2-naphthaleneboronic acid 12.7 g
and tetrakis(triphenylphosphine)palladium 1.7 g were mixed and
substituted with argon. Toluene 220 ml and a 2M sodium carbonate
aqueous solution 110 ml were added thereto, and the mixture was
heated and refluxed for 7 hours.
[0122] After left cooling, the organic layer was extracted with
toluene, and the extract was washed with water and saturated brine.
The organic layer was dried on anhydrous sodium sulfate, and then
the solvent was distilled off. The crystallized product was
filtered and dried, whereby targeted 2-(4-bromophenyl)naphthalene
17.7 g (yield: 85%) was obtained in the form of white crystal.
Synthetic Example 2 synthesis of 9-anthraceneboronic acid
[0123] 9-Bromoanthracene 38.6 g was dissolved in dehydrated toluene
80 ml and dehydrated THF (tetrahydrofuran) 160 ml, and the solution
was cooled to -40.degree. C. A 1.58M n-butyllithium hexane solution
106 ml was dropwise added thereto and stirred at -40.degree. C. for
30 minutes, the temperature was elevated up to -10.degree. C. The
solution was cooled again down to -70.degree. C., and a dehydrated
THF solution of trimethyl borate 50.0 ml was gradually dropwise
added thereto. The solution was stirred at -70.degree. C. for 2
hours and then slowly heated up to room temperature. After left
standing for a night, a 10% hydrochloric acid aqueous solution 100
ml was added thereto and stirred, and then it was extracted twice
with toluene. The organic layer was washed with saturated brine and
dried on anhydrous sodium sulfate. The solvent was distilled off,
and the residue was crystallized from toluene/hexane, filtered and
dried, whereby targeted 9-anthraceneboronic acid 24.4 g was
obtained in the form of pale brown crystal (yield: 73%).
Synthetic Example 3 synthesis of
9-(4-naphthalene-2-yl-phenyl)anthracene
[0124] 9-Anthraceneboronic acid 10.7 g,
2-(4-bromophenyl)naphthalene 11.3 g and
tetrakis(triphenylphosphine)palladium 2.3 g were mixed and
substituted with argon. DME (dimethoxyethane) 140 ml and a 2M
sodium carbonate aqueous solution 60 ml were added thereto, and the
mixture was heated and refluxed for 5 hours.
[0125] After left cooling, the deposited crystal was filtered and
washed with ethanol and toluene. The crystal thus obtained was
recrystallized from toluene, filtered and dried, whereby targeted
(9-(4-naphthalene-2-yl-phenyl)anthracene 13.25 g was obtained
(yield: 87%).
Synthetic Example 4 synthesis of
9-bromo-10-(4-naphthalene-2-yl-phenyl)anthracene
[0126] 9-(4-Naphthalene-2-yl-phenyl)anthracene 13.25 g was
dispersed in DMF (dimethylformamide) 100 ml, and a DMF solution
(100 ml) of NBS (N-bromosuccinimide) 7.44 g was dropwise added
thereto at room temperature. The solution was stirred at room
temperature for 7 hours and then left standing for a nigh. Water
200 ml was added thereto, and the deposited crystal was filtered,
sufficiently washed with ethanol and dried, whereby targeted
(9-bromo-10-(4-naphthalene-2-yl-phenyl)anthracene 15.84 g was
obtained (yield: 99%).
Synthetic Example 5 synthesis of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid
[0127] 9-Bromo-10-(4-naphthalene-2-yl-phenyl)anthracene 13.8 g was
dispersed in dehydrated toluene 80 ml and dehydrated ether 80 ml,
and the mixture was cooled down to -30.degree. C. A 1.58M
n-butyllithium hexane solution 21. 0 ml was dropwise added thereto,
and after the solution was stirred at -40.degree. C. for 30
minutes, the temperature was elevated up to -10.degree. C. The
solution was cooled again down to -70.degree. C., and a dehydrated
ether solution of trimethyl borate 10.0 ml was gradually added
thereto. The solution was stirred at -70.degree. C. for 2 hours and
then gradually heated up to room temperature. After left standing
for a night, a 10% hydrochloric acid aqueous solution 100 ml was
added thereto and stirred, and then it was extracted twice with
toluene. The organic layer was washed with saturated brine and
dried on anhydrous sodium sulfate. The solvent was distilled off,
and the residue was crystallized from toluene/hexane, filtered and
dried, whereby targeted
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid 8.48 g was
obtained in the form of yellow crystal (yield: 67%).
Synthetic Example 6 synthesis of 1-(4-bromophenyl)naphthalene
[0128] 1-(4-Bromophenyl)naphthalene was synthesized by the same
method, except that in Synthetic Example 1, 1-naphthaleneboronic
acid was used in place of 2-naphthaleneboronic acid.
Synthetic Example 7 synthesis of 9-phenanthreneboronic acid
[0129] 9-Phenanthreneboronic acid was synthesized by the same
method, except that in Synthetic Example 2, 9-bromophenanthrene was
used in place of 9-bromoanthracene.
Synthetic Example 8 synthesis of 9-(4-bromophenyl)phenanthrene
[0130] 9-(4-Bromophenyl)phenanthrene was synthesized by the same
method, except that in Synthetic Example 1, 9-phenanthreneboronic
acid was used in place of 2-naphthaleneboronic acid.
Synthetic Example 9 synthesis of
10-(biphenyl-2-yl)anthracene-9-boronic acid
[0131] 10-(Biphenyl-2-yl)anthracene-9-boronic acid was synthesized
by the same method, except that in Synthetic Example 3,
2-bromobiphenyl was used as a starting material in place of
2-(4-bromophenyl)naphthalene.
Synthetic Example 10 synthesis of
9-(4-bromophenyl)-10-phenylanthracene
[0132] 10-Bromoanthracene-9-boronic acid was synthesized by the
same method, except that in Synthetic Example 3, bromobenzene was
used as a starting material in place of
2-(4-bromophenyl)naphthalene. Further, it was turned into
4-bromophenyl by the same method as in Synthetic Example 1 to
synthesize 9-(4-bromophenyl)-10-phenylanthracene.
Synthetic Example 11 synthesis of
10-(4-naphthalene-1-yl-phenyl)anthracene-9-boronic acid
[0133] 10-(4-Naphthalene-1-yl-phenyl)anthracene-9-boronic acid was
synthesized by the same method, except that in Synthetic Example 1,
1-naphthaleneboronic acid was used as a starting material in place
of 2-naphthaleneboronic acid.
Synthetic Example 12 synthesis of 2-(3-bromophenyl)naphthalene
[0134] 2-(3-Bromophenyl)naphthalene was synthesized by the same
method, except that in Synthetic Example 1, 3-bromoiodobenzene was
used in place of 4-bromoiodobenzene.
Synthetic Example 13 synthesis of 2-(2-bromophenyl)naphthalene
[0135] 2-(2-Bromophenyl)naphthalene was synthesized by the same
method, except that in Synthetic Example 1, 2-bromoiodobenzene was
used in place of 4-bromoiodobenzene.
Synthetic Example 14 synthesis of
10-(p-terphenyl-2-yl)anthracene-9-boronic acid
[0136] 10-(p-Terphenyl-2-yl)anthracene-9-boronic acid was
synthesized by the same method, except that in Synthetic Example 3,
2-bromo-p-terphenyl was used as a starting material in place of
2-(4-bromophenyl)naphthalene.
Synthetic Example 15 synthesis of 1-(3-bromophenyl)naphthalene
[0137] 1-(3-Bromophenyl)naphthalene was synthesized by the same
method, except that in Synthetic Example 1, 3-bromoiodobenzene was
used in place of 4-bromoiodobenzene and that 1-naphthaleneboronic
acid was used in place of 2-naphthaleneboronic acid.
Synthetic Example 16 synthesis of
9-(biphenyl-2-yl)-10-(3-bromophenyl)anthracene
[0138] 10-(2-Biphenyl)anthracene-9-boronic acid was synthesized by
the same method, except that in Synthetic Example 3,
2-bromobiphenyl was used as a starting material in place of
2-(4-bromophenyl)naphthalene. Further, it was turned into
3-bromophenyl by the same method as in Synthetic Example 1 to
synthesize 9-(biphenyl-2-yl)-10-(3-bromophenyl)anthracene.
Synthetic Example 17 synthesis of
10-(3-naphthalene-2-yl-phenyl)anthracene-9-boronic acid
[0139] 10-(3-Naphthalene-2-yl-phenyl)anthracene-9-boronic acid was
synthesized by the same method, except that in Synthetic Example 1,
3-bromoiodobenzene was used as a starting material in place of
4-bromoiodobenzene.
Synthetic Example 18 synthesis of 9-(3-bromophenyl)phenanthrene
[0140] 9-(3-Bromophenyl)phenanthrene was synthesized by the same
method, except that in Synthetic Example 1, 9-phenanthreneboronic
acid was used in place of 2-naphthaleneboronic acid and that
3-bromoiodobenzene was used in place of 4-bromoiodobenzene.
Synthetic Example 19 synthesis of 1-(2-bromophenyl)naphthalene
[0141] 1-(3-Bromophenyl)naphthalene was synthesized by the same
method, except that in Synthetic Example 1, 2-bromoiodobenzene was
used in place of 4-bromoiodobenzene and that 1-naphthaleneboronic
acid was used in place of 2-naphthaleneboronic acid.
Synthetic Example 20 synthesis of
2-(3-bromo-5-naphthalene-2-yl-phenyl)naphthalene
[0142] 1,3,5-Tribromoiodobenzene 10 g, 2-naphthaleneboronic acid 12
g and tetrakis(triphenylphosphine)palladium 1.1 g were mixed and
substituted with argon. Toluene 150 ml and a 2M sodium carbonate
aqueous solution 55 ml were added thereto, and the mixture was
heated and refluxed for 7 hours.
[0143] After left cooling, the organic layer was extracted with
toluene, and the extract was washed with water and saturated brine.
The organic layer was dried on anhydrous sodium sulfate, and then
the solvent was distilled off. The product was refined by silica
gel chromatography, whereby targeted
2-(3-bromo-5-naphthalene-2-yl-phenyl)naphthalene 5.5 g (yield: 42%)
was obtained in the form of white crystal.
Synthetic Example 21 synthesis of 2,5-dibromoiodobenzene
[0144] 2,5-Dibromoaniline 10 g was dispersed in diluted
hydrochloric acid (concentrated hydrochloric acid 40 ml+water 30
ml), and an aqueous solution of NaNO.sub.2 3 g was dropwise added
thereto at 0.degree. C. The reaction solution was stirred for 40
minutes and then dropwise added at room temperature to an aqueous
solution of potassium iodide 60 g which was separately prepared.
After stirring at room temperature for 2 hours, methylene chloride
and a small amount of sodium hydrogensulfite were added thereto,
and the organic layer was extracted. The organic layer was washed
with a 10% sodium hydrogensulfite aqueous solution and saturated
brine and dried on anhydrous sodium sulfate, and then the solvent
was distilled off. The product was refined by silica gel
chromatography, whereby targeted 2,5-dibromoiodobenzene 10.5 g
(yield: 73%) was obtained in the form of white crystal.
Synthetic Example 22 synthesis of
10-(4-biphenyl)anthracene-9-boronic acid
[0145] 10-(4-Biphenyl)anthracene-9-boronic acid was synthesized by
the same method, except that in Synthetic Example 3,
4-bromobiphenyl was used as a starting material in place of
2-(4-bromophenyl)naphthalene.
Synthetic Example 23 synthesis of
9-(2,5-dibromophenyl)-10-(4-biphenyl)anthracene
[0146] 9-(2,5-Dibromophenyl)-10-(4-biphenyl)anthracene was
synthesized by the same method, except that in Synthetic Example 3,
2,5-dibromoiodobenzene was used in place of
2-(4-bromophenyl)naphthalene and that
9-(4-biphenyl)anthracene-10-boronic acid was used in place of
9-anthraceneboronic acid.
Synthetic Example 24 synthesis of
2-(5-bromo-2-methylphenyl)naphthalene
[0147] 4-Bromo-2-iodotoluene was synthesized by the same method,
except that in Synthetic Example 21, 5-bromo-2-methylaniline was
used in place of 2,5-dibromoiodoaniline. Further,
2-(5-bromo-2-methylphenyl)naphthalene was synthesized by the same
method, except that in Synthetic Example 1, 4-bromo-2-iodotoluene
was used in place of 4-bromoiodobenzene.
Synthetic Example 25 synthesis of 9-bromo-2-t-butylanthracene
[0148] The same reaction was carried out using 2-t-butylanthracene
in place of 9-(4-naphthalene-2-yl-phenyl)anthracene in Synthetic
Example 4, and the product thus obtained was refined by silica gel
chromatography, whereby 9-bromo-2-t-butylanthracene was
synthesized.
Synthetic Example 26 synthesis of
3-t-butyl-10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic
acid
[0149] 3-t-Butyl-10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic
acid was synthesized by the same method using
9-bromo-2-t-butylanthracene as a starting material in place of
9-bromoanthracene in Synthetic Example 2.
Example 1 Synthesis of Compound AN-8
[0150] 1-(4-Bromophenyl)naphthalene 4.0 g,
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid 5.0 g and
tetrakis(triphenylphosphine)palladium 0.41 g were mixed and
substituted with argon. DME 100 ml and a 2M sodium carbonate
aqueous solution 20 ml were added thereto, and the mixture was
heated and refluxed for 10 hours.
[0151] After left cooling, deposited crystal was filtered and
washed with water, methanol and toluene. The crystal thus obtained
was recrystallized from toluene, filtered and dried, whereby the
targeted compound (AN-8) 4.1 g was obtained in the form of pale
yellow crystal (yield: 60%).
[0152] FD-MS (field desorption mass analysis) of the above compound
gave m/z=582 versus C.sub.46H.sub.30=582.
Example 2 Synthesis of Compound AN-9
[0153] The targeted compound AN-9 was obtained in the form of
cream-colored crystal (yield: 63%) by the same method, except that
in Example 1, 9-(4-bromophenyl)phenanthrene was used in place of
1-(4-bromophenyl)naphthalene.
[0154] FD-MS of the above compound gave m/z=632 versus
C.sub.50H.sub.32=632.
Example 3 Synthesis of Compound NA-45
[0155] The targeted compound AN-45 was obtained in the form of
white crystal (yield: 50%) by the same method, except that in
Example 1,2-(3-bromophenyl)naphthalene was used in place of
1-(4-bromophenyl)naphthalene and that
10-(4-naphthalene-1-yl-phenyl)anthracene-9-boronic acid was used in
place of 10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic
acid.
[0156] FD-MS of the above compound gave m/z=582 versus
C.sub.46H.sub.30=582.
Example 4 Synthesis of Compound AN-117
[0157] The targeted compound AN-117 was obtained in the form of
pale yellow crystal (yield: 68%) by the same method, except that in
Example 1,2-(2-bromophenyl)naphthalene was used in place of
1-(4-bromophenyl)naphthalene and that
10-(4-naphthalene-1-yl-phenyl)anthracene-9-boronic acid was used in
place of 10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic
acid.
[0158] FD-MS of the above compound gave m/z=582 versus
C.sub.46H.sub.30=582.
Example 5 Synthesis of Compound AN-144
[0159] The targeted compound AN-144 was obtained in the form of
pale yellow crystal (yield: 44%) by the same method, except that in
Example 1, 2-bromobiphenyl was used in place of
1-(4-bromophenyl)naphthalene and that
10-(4-naphthalene-1-yl-phenyl)anthracene-9-boronic acid was used in
place of 10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic
acid.
[0160] FD-MS of the above compound gave m/z=532 versus
C.sub.42H.sub.28=532.
Example 6 Synthesis of Compound AN-145
[0161] The targeted compound AN-145 was obtained in the form of
white crystal (yield: 53%) by the same method, except that in
Example 1, 2-bromobiphenyl was used in place of
1-(4-bromophenyl)naphthalene.
[0162] FD-MS of the above compound gave m/z=532 versus
C.sub.42H.sub.28=532.
Example 7 Synthesis of Compound AN-171
[0163] The targeted compound AN-171 was obtained in the form of
pale yellow crystal (yield: 43%) by the same method, except that in
Example 1, 2-bromo-p-terphenyl was used in place of
1-(4-bromophenyl)naphthalene and that
10-(4-naphthalene-1-yl-phenyl)anthracene-9-boronic acid was used in
place of 10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic
acid.
[0164] FD-MS of the above compound gave m/z=608 versus
C.sub.48H.sub.32=608.
Example 8 Synthesis of Compound AN-179
[0165] The targeted compound AN-179 was obtained in the form of
pale yellow crystal (yield: 48%) by the same method, except that in
Example 1,2-(4-bromophenyl)-p-terphenyl was used in place of
1-(4-bromophenyl)naphthalene and that
10-(p-terphenyl-2-yl)anthracene-9-boronic acid was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0166] FD-MS of the above compound gave m/z=710 versus
C.sub.56H.sub.38=710.
Example 9 Synthesis of Compound AN-212
[0167] The targeted compound AN-212 was obtained in the form of
white crystal (yield: 58%) by the same method, except that in
Example 1,1-(3-bromophenyl)naphthalene was used in place of
1-(4-bromophenyl)naphthalene and that
10-(biphenyl-2-yl)anthracene-9-boronic acid was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0168] FD-MS of the above compound gave m/z=532 versus
C.sub.42H.sub.28=532.
Example 10 Synthesis of Compound AN-213
[0169] The targeted compound AN-213 was obtained in the form of
pale yellow crystal (yield: 43%) by the same method, except that in
Example 1,2-(3-bromophenyl)naphthalene was used in place of
1-(4-bromophenyl)naphthalene and that
10-(biphenyl-2-yl)anthracene-9-boronic acid was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0170] FD-MS of the above compound gave m/z=532 versus
C.sub.42H.sub.28=532.
Example 11 Synthesis of Compound AN-237
[0171] The targeted compound AN-237 was obtained in the form of
white crystal (yield: 58%) by the same method, except that in
Example 1,2-(3-bromophenyl)naphthalene was used in place of
1-(4-bromophenyl)naphthalene and that
10-(p-terphenyl-2-yl)anthracene-9-boronic acid was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0172] FD-MS of the above compound gave m/z=608 versus
C.sub.48H.sub.32=608.
Example 12 Synthesis of Compound AN-251
[0173] The targeted compound AN-251 was obtained in the form of
pale yellow crystal (yield: 58%) by the same method, except that in
Example 1,9-(3-bromophenyl)phenanthrene was used in place of
1-(4-bromophenyl)naphthalene and that
10-(3-naphthalene-2-yl-phenyl)anthracene-9-boronic acid was used in
place of 10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic
acid.
[0174] FD-MS of the above compound gave m/z=632 versus
C.sub.50H.sub.32=632.
Example 13 Synthesis of Compound AN-275
[0175] The targeted compound AN-275 was obtained in the form of
pale yellowish white crystal (yield: 45%) by the same method,
except that in Example 1, 1-(2-bromophenyl)naphthalene was used in
place of 1-(4-bromophenyl)naphthalene and that
10-(biphenyl-2-yl)anthracene-9-boronic acid was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0176] FD-MS of the above compound gave m/z=532 versus
C.sub.42H.sub.28=532.
Example 14 Synthesis of Compound NA-281
[0177] The targeted compound NA-281 was obtained in the form of
pale yellowish white crystal (yield: 48%) by the same method,
except that in Example 1, 2-(2-bromophenyl)naphthalene was used in
place of 1-(4-bromophenyl)naphthalene and that
10-(biphenyl-2-yl)anthracene-9-boronic acid was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0178] FD-MS of the above compound gave m/z=532 versus
C.sub.42H.sub.28=532.
Example 15 Synthesis of Compound AN-296
[0179] The targeted compound AN-296 was obtained in the form of
white crystal (yield: 35%) by the same method, except that in
Example 1, 2-bromophenyl-p-terphenyl was used in place of
1-(4-bromophenyl)naphthalene and that
10-(biphenyl-2-yl)anthracene-9-boronic acid was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0180] FD-MS of the above compound gave m/z=558 versus
C.sub.44H.sub.30=558.
Example 16 Synthesis of Compound AN-346
[0181] The targeted compound AN-346 was obtained in the form of
pale yellow crystal (yield: 70%) by the same method, except that in
Example 1,2-(3-bromo-5-naphthalene-2-yl-phenyl)naphthalene was used
in place of 1-(4-bromophenyl)naphthalene.
[0182] FD-MS of the above compound gave m/z=708 versus
C.sub.56H.sub.36=708.
Example 17 Synthesis of Compound AN-358
[0183] The targeted compound AN-358 was obtained in the form of
pale yellow crystal (yield: 62%) by the same method, except that in
Example 1,9-(2,5-dibromophenyl)-10-(4-biphenyl)anthracene was used
in place of 1-(4-bromophenyl)naphthalene and that a twice amount of
1-naphthaleneboronic acid was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0184] FD-MS of the above compound gave m/z=658 versus
C.sub.52H.sub.34=658.
Example 18 Synthesis of Compound AN-393
[0185] The targeted compound AN-393 was obtained in the form of
pale yellow crystal (yield: 64%) by the same method, except that in
Example 1, 2-(5-bromo-2-methylphenyl)naphthalene was used in place
of 1-(4-bromophenyl)naphthalene.
[0186] FD-MS of the above compound gave m/z=596 versus
C.sub.47H.sub.32=596.
Example 19 Synthesis of Compound AN-402
[0187] The targeted compound AN-402 was obtained in the form of
pale yellow crystal (yield: 42%) by the same method, except that in
Example 1, 2-bromobiphenyl was used in place of
1-(4-bromophenyl)naphthalene and that
3-t-butyl-10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid
was used in place of
10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid.
[0188] FD-MS of the above compound gave m/z=588 versus
C.sub.46H.sub.36=588.
Example 20 Production of Organic EL Device
[0189] A glass substrate (manufactured by Geomatech Co., Ltd.) of
25 mm.times.75 mm.times.1.1 mm thickness equipped with an ITO
transparent electrode was subjected to supersonic wave washing in
isopropyl alcohol for 5 minutes and then to UV ozone washing for 30
minutes. After washed, the glass substrate equipped with an ITO
transparent electrode line was loaded in a substrate holder of a
vacuum deposition apparatus, and a
N,N'-bis(N,N'-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4'-diamino-1,1'-biph-
enyl film (hereinafter referred to as a TPD 232 film) shown below
having a film thickness of 60 nm was formed on a face of a side at
which the transparent electrode line was formed so that it covered
the transparent electrode described above. This TPD 232 film
functions as a hole injecting layer. Next, the following
N,N,N',N'-tetra(4-biphenyl)-diaminobiphenylene film (hereinafter
referred to as a TBDB film) having a film thickness of 20 nm was
formed on the above TPD 232 film. This film functions as a hole
transporting layer. Further, the compound AN-8 described above was
deposited to form a film having a film thickness of 40 nm. At the
same time, the following amine compound D1 having a styryl group
was deposited as a luminescent material in a weight ratio of AN-8
to D1=40:3. This film functions as a luminescent layer. An Alq film
having a film thickness of 10 nm was formed on the above film. This
film functions as an electron injecting layer. Then, Li (Li source:
manufactured by Saesgetter Co., Ltd.) which was a reducing dopant
and the following Alq were subjected to binary deposition to form
an Alq:Li film (film thickness: 10 nm) as an electron injecting
layer (or cathode). Metal Al was deposited on the above Alq:Li film
to form a metal cathode, whereby an organic EL device was
formed.
[0190] The depositing temperature (deposition source temperature at
a depositing speed of 1 .ANG./sec) in forming the luminescent layer
was 300.degree. C. Further, a luminous efficiency of the organic EL
device obtained was measured, and a change in the luminance at an
initial luminance of 1000 nit was measured to find that the
luminance after 2443 hours passed since starting observation was
712 nit and that the measurement result of a half life of the above
device was 6050 hours.
##STR00028##
Examples 21 to 22
[0191] Organic EL devices were prepared in the same manner, except
that in Example 20, compounds described in Table 1 were used as
materials for the luminescent layers in place of the compound
AN-8.
[0192] Further, measured in the same manner as in Example 20 were
the depositing temperatures in forming the luminescent layers, the
luminous efficiencies of the organic EL devices obtained and the
half lives at an initial luminance of 1000 nit, and the results
thereof are shown in Table 1.
Example 23
[0193] An organic EL device was prepared in the same manner, except
that in Example 20, the following amine compound D2 was used as a
material for the luminescent layer in place of the amine compound
D1.
[0194] Further, measured in the same manner as in Example 20 were
the depositing temperature in forming the luminescent layer, a
luminous efficiency of the organic EL device obtained and the half
life at an initial luminance of 1000 nit, and the results thereof
are shown in Table 1.
##STR00029##
Examples 24 to 26
[0195] Organic EL devices were prepared in the same manner, except
that in Example 20, AN-45, AN-72 and AN-74 each were used, as
described in Table 1, as materials for the luminescent layers in
place of the compound AN-8.
[0196] Further, measured in the same manner as in Example 20 were
the depositing temperatures in forming the luminescent layers, the
luminous efficiencies of the organic EL devices obtained and the
half lives at an initial luminance of 1000 nit, and the results
thereof are shown in Table 1.
Comparative Examples 1 to 3
[0197] Organic EL devices were prepared in the same manner, except
that in Example 20, the compounds described below and in Table 1
were used as materials for the luminescent layers in place of the
compound AN-8.
[0198] Further, measured in the same manner as in Example 20 were
the depositing temperatures in forming the luminescent layers, the
luminous efficiencies of the organic EL devices obtained and the
half lives at an initial luminance of 1000 nit, and the results
thereof are shown in Table 1.
##STR00030##
TABLE-US-00012 TABLE 1 Compound in Luminous Half Depositing
luminescent efficiency life temperature layer (cd/A) (hour)
(.degree. C.) Example 20 AN-8/D1 11.1 6,050 300 Example 21
AN-213/D1 10.9 4,000 261 Example 22 AN-346/D1 10.7 3,300 254
Example 23 AN-8/D2 10.5 3,800 300 Example 24 AN-45/D1 11.2 6,200
298 Example 25 AN-72/D1 10.9 4,000 262 Example 26 AN-74/D1 11.0
5800 305 Comparative an-1/D1 8.7 900 349 Example 1 Comparative
an-2/D1 8.7 800 331 Example 2 Comparative an-3/D1 8.9 500 310
Example 3
INDUSTRIAL APPLICABILITY
[0199] As explained above in details, an organic EL device prepared
by using a material for an organic EL device comprising the
asymmetric monoanthracene derivative of the present invention
represented by Formula (1) has a high luminous efficiency and a
long life. Accordingly, it is useful as an organic EL device which
is assumed to be continuously used over a long period of time.
Further, use of the compound having a monoanthracene structure of
an asymmetric type represented by the following Formula (1) as a
material for an organic EL device makes it possible to lower a
depositing temperature of the compound and inhibits the compound
from being thermally decomposed in deposition.
* * * * *