U.S. patent application number 15/121472 was filed with the patent office on 2019-02-14 for compound for organic electronic element, organic electronic element using the same, and an electronic device thereof.
This patent application is currently assigned to DUK SAN NEOLUX CO., LTD.. The applicant listed for this patent is DUK SAN NEOLUX CO., LTD.. Invention is credited to DaeSung KIM, Bum Sung LEE, Sun-Hee LEE, Soung Yun MUN, Jung Cheol PARK, Seong Je PARK.
Application Number | 20190051836 15/121472 |
Document ID | / |
Family ID | 54242929 |
Filed Date | 2019-02-14 |
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United States Patent
Application |
20190051836 |
Kind Code |
A2 |
MUN; Soung Yun ; et
al. |
February 14, 2019 |
COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT
USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
Abstract
Provided are a compound of Formula 1 and an organic electric
element including a first electrode, a second electrode, and an
organic material layer between the first electrode and the second
electrode and comprising the compound, the element showing improved
luminescence efficiency, stability, and life span.
Inventors: |
MUN; Soung Yun; (Cheonan-si,
Chungcheongnam-do, KR) ; LEE; Sun-Hee; (Cheonan-si,
Chungcheongnam-do, KR) ; PARK; Jung Cheol; (Suwon-si,
Gyeonggi-do, KR) ; KIM; DaeSung; (Yongin-si,
Gyeonggi-do, KR) ; LEE; Bum Sung; (Cheonan-si,
Chungcheongnam-do, KR) ; PARK; Seong Je; (Busan,
KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
DUK SAN NEOLUX CO., LTD. |
Cheonan-si, Chungcheongnam-do |
|
KR |
|
|
Assignee: |
DUK SAN NEOLUX CO., LTD.
Cheonan-si, Chungcheongnam-do
KR
|
Prior
Publication: |
|
Document Identifier |
Publication Date |
|
US 20160365517 A1 |
December 15, 2016 |
|
|
Family ID: |
54242929 |
Appl. No.: |
15/121472 |
Filed: |
February 25, 2015 |
PCT Filed: |
February 25, 2015 |
PCT NO: |
PCT/KR2015/001801 PCKC 00 |
371 Date: |
August 25, 2016 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
H01L 51/0073 20130101;
H01L 51/0074 20130101; C07D 409/12 20130101; H01L 51/0072 20130101;
H01L 51/5056 20130101; H01L 51/006 20130101; C09K 2211/185
20130101; H01L 51/0081 20130101; H01L 51/0085 20130101; C09K 11/06
20130101; H01L 51/5088 20130101; H01L 51/5012 20130101; C07D 409/04
20130101; Y02E 10/549 20130101; C07D 209/86 20130101; H01L 51/0059
20130101; H01L 51/0067 20130101; H01L 51/0061 20130101; H01L
51/0052 20130101 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C09K 11/06 20060101 C09K011/06; C07D 209/86 20060101
C07D209/86; C07D 409/12 20060101 C07D409/12; C07D 409/04 20060101
C07D409/04 |
Foreign Application Data
Date |
Code |
Application Number |
Feb 27, 2014 |
KR |
10-2014-0023356 |
May 28, 2014 |
KR |
10-2014-0064727 |
Feb 24, 2015 |
KR |
10-2015-0025588 |
Claims
1. A compound of Formula 1: ##STR00196## wherein, Ar.sup.1 to
Ar.sup.3 are each independently selected from the group consisting
of a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a
C.sub.2-C.sub.60 heterocyclic group containing at least one
heteroatom selected from the group consisting of O, N, S, Si, and
P; a fused ring formed by a C.sub.3-C.sub.60 aliphatic ring and a
C.sub.6-C.sub.60 aromatic ring; a C.sub.1-C.sub.50 alkyl group; a
C.sub.2-C.sub.20 alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a
C.sub.1-C.sub.30 alkoxy group; and a C.sub.6-C.sub.30 aryloxy
group, L is ##STR00197## m and o are each an integer of 0 to 4, n
is an integer of 0 to 3, R.sup.1, R.sup.2 and R.sup.3 are each
independently selected from the group consisting of i) deuterium;
halogen; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a
C.sub.2-C.sub.60 heterocyclic group containing at least one
heteroatom selected from the group consisting of O, N, S, Si, and
P; a fused ring formed by a C.sub.3-C.sub.60 aliphatic ring and a
C.sub.6-C.sub.60 aromatic ring; a C.sub.1-C.sub.50 alkyl group; a
C.sub.2-C.sub.20 alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a
C.sub.1-C.sub.30 alkoxy group; a C.sub.6-C.sub.30 aryloxy group;
-L'-N(R.sup.a)(R.sup.b); and combinations thereof, or ii) any two
adjacent groups of R.sup.1, R.sup.2 and R.sup.3 may be optionally
linked together to form at least one ring, and the group(s) not
forming a ring may be the same as defined in the above i), L' is
selected from the group consisting of single bond; a
C.sub.6-C.sub.60 arylene group; a fluorenylene group; a fused ring
formed by a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60
aromatic ring; and a C.sub.2-C.sub.60 heterocyclic group containing
at least one heteroatom selected from the group consisting of O, N,
S, Si, and P, R.sup.a and R.sup.b are each independently selected
from the group consisting of C.sub.6-C.sub.60 aryl group; a
fluorenyl group; a fused ring formed by a C.sub.3-C.sub.60
aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; and a
C.sub.2-C.sub.60 heterocyclic group containing at least one
heteroatom selected from the group consisting of O, N, S, Si, and
P, each of the above aryl group, fluorenyl group, heterocyclic
group, fused ring group, alkyl group, alkenyl group, alkynyl group,
alkoxy group, aryloxy group, arylene group and fluorenylene group
may be substituted with one or more substituents selected from the
group consisting of deuterium; halogen; a silane group; a siloxane
group; a boron group; a germanium group; a cyano group; a nitro
group; a C.sub.1-C.sub.20 alkylthio group; a C.sub.1-C.sub.20
alkoxy group; a C.sub.1-C.sub.20 alkyl group; a C.sub.2-C.sub.20
alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.6-C.sub.20
aryl group; a C.sub.6-C.sub.20 aryl group substituted with
deuterium; a fluorenyl group; a C.sub.2-C.sub.20 heterocyclic group
containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P; a C.sub.3-C.sub.20 cycloalkyl
group; a C.sub.7-C.sub.20 arylalkyl group; and a C.sub.8-C.sub.20
arylalkenyl group.
2. The compound of claim 1 represented by one of Formulas below:
##STR00198## wherein, R' and R'' are each independently selected
from the group consisting of hydrogen; deuterium; tritium; a
C.sub.6-C.sub.20 aryl group; a C.sub.1-C.sub.20 alkyl group; and a
C.sub.2-C.sub.20 alkenyl group, and R' and R'' may be linked
together to form a spiro compound with the carbon to which they are
attached, p is an integer of 0 to 4, q is an integer of 0 to 3,
R.sup.4 and R.sup.5 are each independently selected from the group
consisting of i) deuterium; tritium; halogen; a C.sub.6-C.sub.60
aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic
group containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P; a fused ring formed by a
C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxyl
group; and a C.sub.6-C.sub.30 aryloxy group, and ii) any two
adjacent groups of R.sup.4 and R.sup.5 may be optionally linked
together to form at least one ring, and the groups of R.sup.4s and
R.sup.5s not forming a ring may be the same as defined in the
above.
3. The compound of claim 1, wherein Ar.sup.2 to Ar.sup.3 are each
independently selected from the following structures: ##STR00199##
wherein, Ar.sup.4 is selected from the group consisting of a
C.sub.6-C.sub.60 aryl group; a fluorenyl group; and a
C.sub.2-C.sub.60 heterocyclic group containing at least one
heteroatom selected from the group consisting of O, N, S, Si, and
P, R.sup.6 and R.sup.7 are each independently selected from the
group consisting of i) deuterium; halogen; a C.sub.6-C.sub.60 aryl
group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group
containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P; a fused ring formed by a
C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxy
group; a C.sub.6-C.sub.30 aryloxy group; and
-L'-N(R.sup.a)(R.sup.b), wherein, L' is selected from the group
consisting of single bond; a C.sub.6-C.sub.60 arylene group; a
fluorenylene group; a fused ring formed by a C.sub.3-C.sub.60
aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; and a
C.sub.2-C.sub.60 heterocyclic group containing at least one
heteroatom selected from the group consisting of O, N, S, Si, and
P, and R.sup.a and R.sup.b are each independently selected from the
group consisting of C.sub.6-C.sub.60 aryl group; a fluorenyl group;
a fused ring formed by a C.sub.3-C.sub.60 aliphatic ring and a
C.sub.6-C.sub.60 aromatic ring; and a C.sub.2-C.sub.60 heterocyclic
group containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P, or ii) any two adjacent groups of
R.sup.6 and R.sup.7 may be independently linked together to form at
least one ring, and the groups of R.sup.6s and R.sup.7s not forming
a ring may be the same as defined in the above i), a is an integer
of 0 to 4, wherein plural R.sup.6s may be same or different each
other when a is each 2 or more, b is an integer of 0 to 3, wherein
plural R.sup.7s may be same or different each other when b is each
2 or more.
4. The compound of claim 1, wherein o is 0 (zero), or R.sup.3 is
selected from the following structures: ##STR00200##
5. The compound of claim 1, wherein at least one adjacent groups of
R.sup.1 or R.sup.2 is linked to form a ring.
6. The compound of claim 5 represented by one of Formulas below:
##STR00201## ##STR00202## wherein Ar.sup.1 to Ar.sup.3, L, R.sup.1,
m and n are the same as defined in claim 1.
7. The compound of claim 1 represented by one of Formulas below:
##STR00203## ##STR00204## ##STR00205## wherein Ar.sup.2, Ar.sup.3,
L, R.sup.1, R.sup.2, m and n are the same as defined in claim 1, X
is O, S or C(R')(R''), R' and R'' are each independently selected
from the group consisting of hydrogen; deuterium; tritium; a
C.sub.6-C.sub.20 aryl group; a C.sub.1-C.sub.20 alkyl group; and a
C.sub.2-C.sub.20 alkenyl group, and R' and R'' may be linked
together to form a spiro compound with the carbon to which they are
attached, p is an integer of 0 to 4, q is an integer of 0 to 3,
R.sup.4 and R.sup.5 are each independently selected from the group
consisting of i) deuterium; tritium; halogen; a C.sub.6-C.sub.60
aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic
group containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P; a fused ring formed by a
C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxyl
group; and a C.sub.6-C.sub.30 aryloxy group, and ii) any two
adjacent groups of R.sup.4 and R.sup.5 may be optionally linked
together to form at least one ring, and the groups of R.sup.4s and
R.sup.5s not forming a ring may be the same as defined in the
above.
8. The compound of claim 1 represented by the following Formula:
##STR00206## wherein R.sup.1, R.sup.2, m, n, Ar.sup.1, Ar.sup.3 and
L are the same as defined in Formula 1, Ar.sup.4 is selected from
the group consisting of a C.sub.6-C.sub.60 aryl group; a fluorenyl
group; and a C.sub.2-C.sub.60 heterocyclic group containing at
least one heteroatom selected from the group consisting of O, N, S,
Si, and P, R.sup.6 and R.sup.7 are each independently selected from
the group consisting of i) deuterium; halogen; a C.sub.6-C.sub.60
aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic
group containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P; a fused ring formed by a
C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxy
group; a C.sub.6-C.sub.30 aryloxy group; and
-L'-N(R.sup.a)(R.sup.b), wherein, L' is selected from the group
consisting of single bond; a C.sub.6-C.sub.60 arylene group; a
fluorenylene group; a fused ring formed by a C.sub.3-C.sub.60
aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; and a
C.sub.2-C.sub.60 heterocyclic group containing at least one
heteroatom selected from the group consisting of O, N, S, Si, and
P, and R.sup.a and R.sup.b are each independently selected from the
group consisting of C.sub.6-C.sub.60 aryl group; a fluorenyl group;
a fused ring formed by a C.sub.3-C.sub.60 aliphatic ring and a
C.sub.6-C.sub.60 aromatic ring; and a C.sub.2-C.sub.60 heterocyclic
group containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P, or ii) any two adjacent groups
may be independently linked together to form at least one ring, and
the groups of R.sup.6s and R.sup.7s not forming a ring may be the
same as defined in the above i), a is an integer of 0 to 4, wherein
plural R.sup.6s may be same or different each other when a is each
2 or more, b is an integer of 0 to 3, wherein plural R.sup.7s may
be same or different each other when b is each 2 or more.
9. The compound of claim 8 represented by the following Formulas:
##STR00207## wherein, R.sup.1, R.sup.2, R.sup.6, R.sup.7, a, b, m,
n, Ar.sup.1, Ar.sup.3, Ar.sup.4 and L are the same as defined in
claim 8.
10. The compound of claim 1, wherein Formula 1 is any one of the
compounds below: ##STR00208## ##STR00209## ##STR00210##
##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215##
##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220##
##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225##
##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230##
##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235##
##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240##
##STR00241## ##STR00242## ##STR00243##
11. An organic electric element comprising a first electrode, a
second electrode, and an organic material layer disposed between
the first electrode and the second electrode, wherein the organic
material layer comprises the compound of claim 1.
12. The organic electric element of claim 11, wherein the organic
material layer comprises at least one of a hole injection layer, a
hole transport layer, an emission-auxiliary layer and an emitting
layer, and at least one of the layers comprises the compound in the
same kind or two or more different kinds.
13. The organic electric element of claim 11, wherein the organic
electric element further comprises at least one layer to improve
luminescence efficiency, formed on at least one of the sides of the
first and second electrodes opposite to the organic material
layer.
14. The organic electric element of claim 11, wherein the organic
material layer is formed by any one of the processes of spin
coating, nozzle printing, inkjet printing, slot coating, dip
coating and roll-to-roll.
15. An electronic device comprising a display device, which
comprises the organic electric element of claim 11, and a control
unit for driving the display device.
16. The electronic device of claim 15, wherein the organic electric
element comprises at least one of an organic light emitting diode,
an organic solar cell, an organic photo conductor, an organic
transistor, and an element for monochromatic or white illumination.
Description
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This patent application claims benefit under 35 U.S.C.
119(e), 120, 121, or 365(c), and is a National Stage entry from
International Application No. PCT/KR2015/001801 filed on Feb. 25,
2015, which claims priority to Korean Patent Application No.
10-2014-0023356 filed on Feb. 27, 2014, Korean Patent Application
No. 10-2014-0064727 filed on May 28, 2014, and Korean Patent
Application No. 10-2015-0025588 filed on Feb. 24, 2015, the
contents of which are hereby incorporated by reference for all
purposes as if fully set forth herein.
BACKGROUND
Technical Field
[0002] The present invention relates to compounds for organic
electric elements, organic electric elements using the same, and
electronic devices thereof.
Background Art
[0003] In general, an organic light emitting phenomenon refers to a
phenomenon in which electric energy is converted into light energy
of an organic material. An organic electric element utilizing the
organic light emitting phenomenon usually has a structure including
an anode, a cathode, and an organic material layer interposed
therebetween. In many cases, the organic material layer may have a
multilayered structure including multiple layers made of different
materials in order to improve the efficiency and stability of an
organic electric element, and for example, may include a hole
injection layer, a hole transport layer, a light emitting layer, an
electron transport layer, an electron injection layer, or the
like.
[0004] A material used as an organic material layer in an organic
electric element may be classified into a light emitting material
and a charge transport material, for example, a hole injection
material, a hole transport material, an electron transport
material, an electron injection material, and the like according to
its function.
[0005] Currently, the power consumption is required more and more
as size of display becomes larger and larger in the portable
display market. Therefore, the power consumption is a very
important factor in the portable display with a limited power
source of the battery, and efficiency and life span issue also must
be solved.
[0006] Efficiency, life span, driving voltage, and the like are
correlated with each other. For example, if efficiency is
increased, then driving voltage is relatively lowered, and the
crystallization of an organic material due to Joule heating
generated during operation is reduced as driving voltage is
lowered, as a result of which life span shows a tendency to
increase.
[0007] However, efficiency cannot be maximized only by simply
improving the organic material layer. This is because long life
span and high efficiency can be simultaneously achieved when an
optimal combination of energy levels and T1 values, inherent
material properties (mobility, interfacial properties, etc.), and
the like among the respective layers included in the organic
material layer is given. Therefore it is required to develop a
light emitting material that has high thermal stability and can
achieve efficiently a charge balance in the light-emitting
layer.
[0008] Further, in order to solve the emission problem with a hole
transport layer in a recent organic electric element, an
emission-auxiliary layer is present between the hole transport
layer and a light emitting layer, and it is time to develop
different emission-auxiliary layers according to respective light
emitting layers (R, G, B).
[0009] In general, an electron transferred from an electron
transport layer to a light emitting layer and a hole transferred
from a hole transport layer to the light emitting layer are
recombined to form an exciton.
[0010] However, since a material used in a hole transporting layer
should have a low HOMO value, it mainly has a low T1 value. Due to
this, excitons generated from a light emitting layer are
transported to the hole transporting layer, resulting in a charge
unbalance in the light emitting layer. Thus, light emission occurs
in the hole transporting layer or at an interface of the hole
transporting layer so that the organic electroluminescent device is
reduced in color purity, efficiency, and lifespan.
[0011] Also, when using a material having rapid hole mobility for
reducing a driving voltage, this is tend to decrease the
efficiency. In an OLEDs, a charge unbalance in the light emitting
layer is caused because of that hole mobility is faster than
electron mobility, and reduced efficiency and lifespan is
happened.
[0012] Therefore, an emitting auxiliary layer must be formed by a
material what can solve the problems of an hole transport layer,
having hole mobility (within the driving voltage range of the blue
element of full device) to give the suitable driving voltage, high
T1 energy value (electron block) and wide band gap. These
requirements are not satisfied only by structural characteristics
about a core of the emitting auxiliary layer's material. Therefore,
it is necessary to develop of the material for the emitting
auxiliary layer having high T1 energy value and wide band gap, to
improve efficiency and lifespan of the organic electric element as
combined core of material and characteristics of sub substituents
appropriately.
[0013] In order to allow an organic electric element to fully
exhibit the above-mentioned excellent features, it should be
prerequisite to support a material constituting an organic material
layer in the element, for example, a hole injection material, a
hole transport material, a light emitting material, an electron
transport material, an electron injection material, or the like, by
a stable and efficient material. However, such a stable and
efficient organic material layer material for an organic electric
element has not yet been fully developed. Accordingly, there is a
continuous need to develop new materials for an organic material
layer.
SUMMARY
[0014] In order to solve one or more of the above-mentioned
problems occurring in the prior art, an aspect of the present
invention is to provide a compound which allows an organic electric
element to improve in luminescence efficiency, stability and
lifespan, an organic electric element containing the same, and an
electronic device including the organic electric element.
[0015] In accordance with an aspect of the present invention, the
compound represented by the following Formula is provided.
##STR00001##
[0016] In another aspect of the present invention, organic electric
elements containing the compound represented by the formula above
and electronic devices including the organic electric element are
provided.
[0017] By employing the compound of the present invention that has
wide band gap and high T1 energy value due to the non-linear linker
(L) attached to the carbazole core, the organic electric element
according to one or more embodiments of the present invention can
have not only high luminescence efficiency and high
heat-resistance, but also significantly improved color purity and
lifespan.
BRIEF DESCRIPTION OF THE DRAWINGS
[0018] FIG. 1 illustrates an example of an organic light emitting
diode according to an embodiment of the present invention.
DETAILED DESCRIPTION
[0019] Hereinafter, some embodiments of the present invention will
be described in detail with reference to the accompanying
illustrative drawings.
[0020] In designation of reference numerals to components in
respective drawings, it should be noted that the same elements will
be designated by the same reference numerals although they are
shown in different drawings. Further, in the following description
of the present invention, a detailed description of known functions
and configurations incorporated herein will be omitted when it may
make the subject matter of the present invention rather
unclear.
[0021] In addition, terms, such as first, second, A, B, (a), (b) or
the like may be used herein when describing components of the
present invention. Each of these terminologies is not used to
define an essence, order or sequence of a corresponding component
but used merely to distinguish the corresponding component from
other component(s). It should be noted that if it is described in
the specification that one component is "connected," "coupled" or
"joined" to another component, a third component may be
"connected," "coupled," and "joined" between the first and second
components, although the first component may be directly connected,
coupled or joined to the second component. In addition, it will be
understood that when an element such as a layer, film, region or
substrate is referred to as being "on" or "over" another element,
it can be directly on the other element or intervening elements may
also be present. In contrast, when an element is referred to as
being "directly on" another element, there are no intervening
elements present.
[0022] As used in the specification and the accompanying claims,
unless otherwise stated, the following is the meaning of the term
as follows.
[0023] Unless otherwise stated, the term "halo" or "halogen" as
used herein includes fluorine (F), chlorine (Cl), bromine (Br), or
iodine (I).
[0024] Unless otherwise stated, the term "alkyl" or "alkyl group"
as used herein has a single bond of 1 to 60 carbon atoms, and means
aliphatic functional radicals including a linear alkyl group, a
branched chain alkyl group, a cyclo alkyl group (alicyclic), or an
alkyl group substituted with a cyclo alkyl.
[0025] Unless otherwise stated, the term "halo alkyl" or "halogen
alkyl" as used herein includes an alkyl group substituted with a
halogen.
[0026] Unless otherwise stated, the term "alkenyl" or "alkynyl" as
used herein has, but not limited to, double or triple bonds of 2 to
60 carbon atoms, and includes a linear alkyl group, or a branched
chain alkyl group.
[0027] Unless otherwise stated, the term "cyclo alkyl" as used
herein means, but not limited to, alkyl forming a ring having 3 to
60 carbon atoms.
[0028] The term "alkoxyl group", "alkoxy group" or "alkyloxy group"
as used herein means an oxygen radical attached to an alkyl group,
but not limited to, and has 1 to 60 carbon atoms.
[0029] The term "alkenoxyl group", "alkenoxy group", "alkenyloxyl
group" or "alkenyloxy group" as used herein means an oxygen radical
attached to an alkyl group, but not limited to, and has 2 to 60
carbon atoms.
[0030] The term "aryloxyl group" or "aryloxy group" as used herein
means an oxygen radical attached to an aryl group, but not limited
to, and has 6 to 60 carbon atoms.
[0031] Unless otherwise stated, the term "aryl group" or "arylene
group" as used herein has, but not limited to, 6 to 60 carbon
atoms. Herein, the aryl group or arylene group means a monocyclic
or polycyclic aromatic group, and may also be formed in conjunction
with an adjacent group. Examples of "aryl group" or "arylene group"
may include a phenyl group, a biphenyl group, a fluorene group, or
a spirofluorene group or a spirobifluorene group.
[0032] Also, when prefixes are named subsequently, it means that
substituents are listed in the order described first. For example,
an aryl alkoxy means an alkoxy substituted with an aryl, an alkoxyl
carbonyl means a carbonyl substituted with an alkoxyl, and an aryl
carbonyl alkenyl also means an alkenyl substitutes with an aryl
carbonyl, wherein the aryl carbonyl may be a carbonyl substituted
with an aryl.
[0033] Unless otherwise stated, the "hetero aryl group" or "hetero
arylene group" as used herein means, but not limited to, a ring
containing one or more hetero atoms, and having 2 to 60 carbon
atoms. They include at least one monocyclic or polycyclic ring, and
may be linked together to form a fused ring.
[0034] Unless otherwise stated, the term "heterocyclic group" as
used herein means, but not limited to, a ring containing one or
more hetero atoms, and having 2 to 60 carbon atoms. They include at
least one monocyclic or polycyclic ring, and hetero aliphatic or
hetero aromatic ring, and may be linked together to form a fused
ring.
[0035] Unless otherwise stated, the term "heteroatom" as used
herein represents at least one of N, O, S, P, and Si.
[0036] Also, the term "heterocyclic group" may include SO.sub.2
instead of carbon consisting of cycle. For example, "heterocyclic
group" includes compound below.
##STR00002##
[0037] Unless otherwise stated, the term "aliphatic" as used herein
means aliphatic hydrocarbon, having 1 to 60 carbon atoms. The term
"aliphatic ring" means aliphatic hydrocarbon ring, having 1 to 60
carbon.
[0038] Unless otherwise stated, the term "ring" as used herein
means aliphatic ring having 3 to 60 carbon or aromatic ring having
6 to 60 carbon, or heterocyclic ring having 2 to 60 carbon or a
fused ring formed by combinations thereof, includes saturated or
unsaturated ring.
[0039] The other hetero cyclic compounds or hetero radicals may
include, but not limited to, at least one hetero atom, except to
the described hetero cyclic compound above.
[0040] Unless otherwise stated, the term "substituted or
unsubstituted" as used herein means that substitution is carried
out by at least one substituent selected from the group consisting
of, but not limited to, deuterium, halogen, an amino group, a
nitrile group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a
C.sub.1-C.sub.20 alkoxy group, a C.sub.1-C.sub.20 alkylamine group,
a C.sub.1-C.sub.20 alkylthio group, a C.sub.6-C.sub.20 arylthio
group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.2-C.sub.20 alkynyl
group, a C.sub.3-C.sub.20 cycloalkyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.20 aryl group substituted by deuterium, a
C.sub.8-C.sub.20 arylalkenyl group, a silane group, a boron group,
a germanium group, and a C.sub.2-C.sub.20 heterocyclic group.
[0041] Otherwise specified, the Formulas used in the present
invention are as defined in the index definition of the substituent
of the following Formula.
##STR00003##
[0042] Wherein, when a is an integer of zero, the substituent
R.sup.1 is absent, when a is an integer of 1, the sole R.sup.1 is
linked to any one of the carbon atoms constituting the benzene
ring, when a is an integer of 2 or 3, the substituent R.sup.1s may
be the same and different, and are linked to the benzene ring as
follows. when a is an integer of 4 to 6, the substituents R.sup.1s
may be the same and different, and are linked to the benzene ring
in a similar manner to that when a is an integer of 2 or 3,
hydrogen atoms linked to carbon constituents of the benzene ring
being not represented as usual.
##STR00004##
[0043] FIG. 1 illustrates an organic electric element according to
an embodiment of the present invention.
[0044] Referring to FIG. 1, an organic electric element 100
according to an embodiment of the present invention includes a
first electrode 120 formed on a substrate 110, a second electrode
180, and an organic material layer between the first electrode 110
and the second electrode 180, which contains the inventive
compound. Here, the first electrode 120 may be an anode (positive
electrode), and the second electrode 180 may be a cathode (negative
electrode). In the case of an inverted organic electric element,
the first electrode may be a cathode, and the second electrode may
be an anode.
[0045] The organic material layer includes a hole injection layer
130, a hole transport layer 140, a light emitting layer 150, an
electron transport layer 160, and an electron injection layer 170
formed in sequence on the first electrode 120. Here, the layers
included in the organic material layer, except the light emitting
layer 150, may not be formed. The organic material layer may
further include a hole blocking layer, an electron blocking layer,
an emission-auxiliary layer 151, a buffer layer 141, etc., and the
electron transport layer 160 and the like may serve as the hole
blocking layer.
[0046] Although not shown, the organic electric element according
to an embodiment of the present invention may further include at
least one protective layer or one capping layer formed on at least
one of the sides the first and second electrodes, which is a side
opposite to the organic material layer.
[0047] The inventive compound employed in the organic material
layer may be used as a host material, a dopant material, or a
capping layer material in the hole injection layer 130, the hole
transport layer 140, the electron transport layer 160, the electron
injection layer 170, or the light emitting layer 150. For example,
the inventive compound may be used as the light emitting layer 150,
the hole transport layer 140, and/or the emission-auxiliary layer
151.
[0048] Since depending on the type and position of a substituent to
be attached, a band gap, electrical properties, interfacial
properties, and the like may vary even in the same core, it is very
important what the types of core and a combination of substituent
attached to the core are. Specially, long life span and high
efficiency can be simultaneously achieved when an optimal
combination of energy levels and T1 values, inherent material
properties (mobility, interfacial properties, etc.), and the like
among the respective layers included in the organic material layer
is given.
[0049] As already described above, in order to solve the emission
problem with a hole transport layer in a conventional organic
electric element, an emission-auxiliary layer is preferably formed
between the hole transport layer and a light emitting layer, and it
is time to develop different emission-auxiliary layers according to
respective light emitting layers (R, G, B). However, even when a
similar core is used, it is very difficult to infer the
characteristics of an emission-auxiliary layer if a used organic
material layer varies because the correlation between the
emission-auxiliary layer and a hole transport layer and the
correlation between the emission-auxiliary layer and a light
emitting layer (host) mused be discovered.
[0050] Accordingly, in the present invention, a combination of
energy levels and T1 values, inherent material properties
(mobility, interfacial properties, etc.), and the like among the
respective layers included in the organic material layer is
optimized by forming a light emitting layer and/or an
emission-auxiliary layer by using the compound represented by
Formula 1, and thus the life span and efficiency of the organic
electric element can be improved at the same time.
[0051] The organic electric element according to an embodiment of
the present invention may be manufactured using various deposition
methods. The organic electric element according to an embodiment of
the present invention may be manufactured using a PVD (physical
vapor deposition) method or CVD (chemical vapor deposition) method.
For example, the organic electric element may be manufactured by
depositing a metal, a conductive metal oxide, or a mixture thereof
on the substrate to form the anode 120, forming the organic
material layer including the hole injection layer 130, the hole
transport layer 140, the light emitting layer 150, the electron
transport layer 160, and the electron injection layer 170 thereon,
and then depositing a material, which can be used as the cathode
180, thereon. Also, an emitting auxiliary layer 151 may be
comprised between the hole transport layer 140 and the light
emitting layer 150.
[0052] And also, the organic material layer may be manufactured in
such a manner that a smaller number of layers are formed using
various polymer materials by a soluble process or solvent process,
for example, spin coating, dip coating, doctor blading, screen
printing, inkjet printing, or thermal transfer, instead of
deposition. Since the organic material layer according to the
present invention may be formed in various ways, the scope of
protection of the present invention is not limited by a method of
forming the organic material layer.
[0053] According to used materials, the organic electric element
according to an embodiment of the present invention may be of a top
emission type, a bottom emission type, or a dual emission type.
[0054] A WOLED (White Organic Light Emitting Device) readily allows
for the formation of ultra-high definition images, and is of
excellent processability as well as enjoying the advantage of being
produced using conventional color filter technologies for LCDs. In
this regard, various structures for WOLEDs, used as back light
units, have been, in the most part, suggested and patented.
Representative among the structures are a parallel side-by-side
arrangement of R(Red), G (Green), B (Blue) light-emitting units, a
vertical stack arrangement of RGB light-emitting units, and a CCM
(color conversion material) structure in which electroluminescence
from a blue (B) organic light emitting layer, and photoluminescence
from an inorganic luminescent using the electroluminescence are
combined. The present invention is applicable to these WOLEDs.
[0055] Further, the organic electric element according to an
embodiment of the present invention may be any one of an organic
light emitting diode (OLED), an organic solar cell, an organic
photo conductor (OPC), an organic transistor (organic TFT), and an
element for monochromatic or white illumination.
[0056] Another embodiment of the present invention provides an
electronic device including a display device, which includes the
above described organic electric element, and a control unit for
controlling the display device. Here, the electronic device may be
a wired/wireless communication terminal which is currently used or
will be used in the future, and covers all kinds of electronic
devices including a mobile communication terminal such as a
cellular phone, a personal digital assistant (PDA), an electronic
dictionary, a point-to-multipoint (PMP), a remote controller, a
navigation unit, a game player, various kinds of TVs, and various
kinds of computers.
[0057] Hereinafter, an organic electric element according to an
aspect of the present invention will be described.
[0058] The compound according to an aspect of the present invention
is represented by the following Formula 1.
##STR00005##
[0059] In Formula 1 above, Ar.sup.1 to Ar.sup.3 may be each
independently selected from the group consisting of a
C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60
heterocyclic group containing at least one heteroatom selected from
the group consisting of O, N, S, Si, and P; a fused ring formed by
a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxy
group; and a C.sub.6-C.sub.30 aryloxy group. For example, Ar.sup.1
to Ar.sup.3 may be each independently phenyl, naphthyl, biphenyl,
terphenyl, phenyl substituted with deuterium, methyl phenyl,
t-butyl phenyl, methoxy phenyl, terphenyl substituted with
deuterium, 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl,
7,7-diphenyl-7H-benzo[c]fluorenyl, spirobifluorenyl,
9-phenyl-9H-carbazolyl, 9-naphthyl-9H-carbazolyl,
9-biphenyl-9H-carbazolyl, 9-triazinyl-9H-carbazolyl,
9-dibenzothienyl-9H-carbazolyl, 7-phenyl-7H-benzo[c]carbazolyl,
5-phenyl-5H-benzo[b]carbazolyl, 11-phenyl-11H-benzo[a]carbazolyl,
dibenzothienyl, dibenzofuryl, naphto[2,1-b]benzothienyl,
naphto[2,1-b]benzofuryl or phenylpyrimidinyl.
[0060] L may be
##STR00006##
wherein, R.sup.3 may be selected from the group consisting of i)
deuterium; halogen; a C.sub.6-C.sub.60 aryl group; a fluorenyl
group; a C.sub.2-C.sub.60 heterocyclic group containing at least
one heteroatom selected from the group consisting of O, N, S, Si,
and P; a fused ring formed by a C.sub.3-C.sub.60 aliphatic ring and
a C.sub.6-C.sub.60 aromatic ring; a C.sub.1-C.sub.50 alkyl group; a
C.sub.2-C.sub.20 alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a
C.sub.1-C.sub.30 alkoxy group; a C.sub.6-C.sub.30 aryloxy group;
-L'-N(R.sup.a)(R.sup.b); and combinations thereof, or ii) two
adjacent groups, may be optionally linked together to form at least
one ring, and the group(s) of R.sup.3s not forming a ring may be
the same as defined in the above i). For example, R.sup.3 may be
phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, quinolyl,
isoquinolyl, quinazolyl, or adjacent R.sup.3s may be linked
together to form at least one aromatic ring such as naphthalene or
phenanthrene, or hetero cyclic ring such as isoquinoline,
quinoline, quinazoline or quinoxaline with the benzene ring to
which R.sup.3s are attached.
[0061] o may be an integer of 0 to 4, plural R.sup.3s may be same
or different each other when o is 2 or more. And all of or some of
the adjacent groups, R.sup.3s, may be linked together to form a
ring, and the group(s) of R.sup.3s not forming a ring may be any
one of substituents as defined in the above i).
[0062] In Formula 1 above, m may be an integer of 0 to 4, and n may
be an integer of 0 to 3.
[0063] R.sup.1 and R.sup.2 may be each independently selected from
the group consisting of i) deuterium; halogen; a C.sub.6-C.sub.60
aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic
group containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P; a fused ring formed by a
C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxy
group; a C.sub.6-C.sub.30 aryloxy group; and
-L'-N(R.sup.a)(R.sup.b), or ii) any two adjacent groups may be
optionally linked together to form at least one ring, and the
group(s) of R.sup.1 and R.sup.2 not forming a ring may be the same
as defined in the above i). For example, R.sup.1 and R.sup.2 may be
each independently propenyl, phenyl, dibenzothienyl, triazinyl,
quinolyl or quinazolyl, adjacent R.sup.1s and/or R.sup.2s may be
linked together to form an aromatic ring such as naphthalene or
phenanthrene, or hetero cyclic ring such as isoquinoline,
quinoline, quinazoline or quinoxaline, with the benzene ring to
which they are attached.
[0064] Plural R.sup.1s may be same or different each other when m
is 2 or more, and all of some of the adjacent groups, R.sup.1s, may
be linked together to form a ring. The same applies to plural
R.sup.2s where n is 2 or more, and all of or some of the adjacent
groups, R.sup.2s, may be linked together to form a ring.
[0065] Meanwhile, a fused ring formed by adjacent groups may be a
C.sub.3-C.sub.60 aliphatic ring or a C.sub.6-C.sub.60 aromatic
ring, a C.sub.2-C.sub.60 hetero cyclic ring, a C.sub.3-C.sub.60
alicyclic ring, or a fused ring formed y combinations thereof, and
it may be a monocyclic or polycyclic ring, and/or a saturated or
unsaturated ring.
[0066] L' may be selected from the group consisting of single bond;
a C.sub.6-C.sub.60 arylene group; a fluorenylene group; a fused
ring formed by a C.sub.3-C.sub.60 aliphatic ring and a
C.sub.6-C.sub.60 aromatic ring; and a C.sub.2-C.sub.60 heterocyclic
group containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P, R.sup.a and R.sup.b may be each
independently selected from the group consisting of
C.sub.6-C.sub.60 aryl group; a fluorenyl group; a fused ring formed
by a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60
aromatic ring; and a C.sub.2-C.sub.60 heterocyclic group containing
at least one heteroatom selected from the group consisting of O, N,
S, Si, and P.
[0067] For example, in Formula 1 above, Ar.sup.1 may be selected
from the following structures:
##STR00007##
[0068] wherein R' and R'' may be each independently selected from
the group consisting of hydrogen; deuterium; tritium; a
C.sub.6-C.sub.20 aryl group; a C.sub.1-C.sub.20 alkyl group; and a
C.sub.2-C.sub.20 alkenyl group. For example, R' and R'' may be each
independently methyl or phenyl, and R' and R'' may be linked
together to form a spiro compound with the carbon to which they are
attached.
[0069] R.sup.4 and R.sup.5 may be each independently selected from
the group consisting of deuterium; tritium; halogen; a
C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60
heterocyclic group containing at least one heteroatom selected from
the group consisting of O, N, S, Si, and P; a fused ring formed by
a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxyl
group; and a C.sub.6-C.sub.30 aryloxy group, and any two adjacent
groups may be optionally linked together to form at least one ring.
Herein, the groups of R.sup.4s and R.sup.5s not forming a ring may
be the same as defined in the above.
[0070] p may be an integer of 0 to 4, q may be an integer of 0 to
3. When p and/or q are 2 or more, plural R.sup.4s may be same or
different each other, and plural R.sup.5s may be same or different
each other. Further, all of or some of adjacent R.sup.4s may be
linked together to form one or more ring, and all of or some of
adjacent R.sup.5s may be linked together to form one or more ring.
Furthermore, for example, adjacent R.sup.4s may be linked together
to form a ring, and adjacent R.sup.5s may be each independently
aryl group or hetero cyclic ring.
[0071] The ring formed by linking between adjacent groups may be a
C.sub.3-C.sub.60 aliphatic ring or a C.sub.6-C.sub.60 aromatic
ring, a C.sub.2-C.sub.60 hetero ring, a C.sub.3-C.sub.60 alicyclic
ring, or a fused ring formed by combinations thereof, and the ring
may be a mono cyclic or poly cyclic ring, and/or saturated or
unsaturated ring.
[0072] Also, Ar.sup.2 and Ar.sup.3 in Formula 1 above may be
selected from the following structures:
##STR00008##
[0073] wherein, Ar.sup.4 may be selected from the group consisting
of a C.sub.6-C.sub.60 aryl group; a fluorenyl group; and a
C.sub.2-C.sub.60 heterocyclic group containing at least one
heteroatom selected from the group consisting of O, N, S, Si, and
P. For example, Ar.sup.4 may be phenyl, biphenyl, naphthyl,
pyridyl, 9,9-dimethyl-9H-fluorenyl, triazinyl, phenyl substituted
with deuterium, or dibenzothienyl.
[0074] R.sup.6 and R.sup.7 may be each independently selected from
the group consisting of deuterium; halogen; a C.sub.6-C.sub.60 aryl
group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group
containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P; a fused ring formed by a
C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxy
group; a C.sub.6-C.sub.30 aryloxy group; and
-L'-N(R.sup.a)(R.sup.b). Herein L', R.sup.a and R.sup.b may be the
same as defined in above R.sup.1 to R.sup.3.
[0075] Further, any two adjacent R.sup.6s and R.sup.7s may be
independently linked together to form at least one ring, and the
groups of R.sup.6s and R.sup.7s not forming a ring may be the same
as defined in the above. For example, adjacent R.sup.6s and/or
R.sup.7s may be optionally linked together to form an aromatic ring
such as naphthalene or phenanthrene, or hetero cyclic ring such as
isoquinoline, quinoline, quinazoline or quinoxaline, with the
benzene ring to which they are attached.
[0076] Further, a may be an integer of 0 to 4, b may be an integer
of 0 to 3. wherein each of plural R.sup.6s and plural R.sup.7s may
be same or different each other when a and b are each 2 or more.
All of or some of adjacent R.sup.6s may be linked together to form
at least one ring, all of or some of adjacent R.sup.7s may be
linked together to form at least one ring, and even though adjacent
R.sup.6s may be linked together to form a ring, adjacent R.sup.7s
may be each independently aryl group or hetero cyclic ring.
[0077] The ring formed by adjacent groups may be a C.sub.3-C.sub.60
aliphatic ring or a C.sub.6-C.sub.60 aromatic ring, a
C.sub.2-C.sub.60 hetero ring, a C.sub.3-C.sub.60 alicyclic ring, or
a fused ring formed by combinations thereof, and it may be a mono
cyclic or poly cyclic ring, and/or saturated or unsaturated
ring.
[0078] Each of the above aryl group, fluorenyl group, heterocyclic
group, fused ring group, alkyl group, alkenyl group, alkynyl group,
alkoxy group, aryloxy group, arylene group and fluorenylene group
may be substituted with one or more substituents selected from the
group consisting of deuterium; halogen; a silane group; a siloxane
group; a boron group; a germanium group; a cyano group; a nitro
group; a C.sub.1-C.sub.20 alkylthio group; a C.sub.1-C.sub.20
alkoxy group; a C.sub.1-C.sub.20 alkyl group; a C.sub.2-C.sub.20
alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.6-C.sub.20
aryl group; a C.sub.6-C.sub.20 aryl group substituted with
deuterium; a fluorenyl group; a C.sub.2-C.sub.20 heterocyclic group
containing at least one heteroatom selected from the group
consisting of O, N, S, Si, and P; a C.sub.3-C.sub.20 cycloalkyl
group; a C.sub.7-C.sub.20 arylalkyl group; and a C.sub.8-C.sub.20
arylalkenyl group.
[0079] Specifically, the compounds represented by Formula 1 above
may be represented any one of the following Formulas, and the
following Formulas represent the cases when adjacent R.sup.1s
and/or adjacent R.sup.2s may be linked together to form a ring.
##STR00009## ##STR00010##
[0080] In Formulas 2 to 10 above, each symbols of Ar.sup.1 to
Ar.sup.3, L, R.sup.1, m and n may be the same as defined in Formula
1 above.
[0081] Specifically, the compounds represented by Formula 1 above
may be represented any one of the following Formulas:
##STR00011## ##STR00012## ##STR00013##
[0082] In Formulas 11 to 20, each symbols of Ar.sup.2, Ar.sup.3, L,
R.sup.1, R.sup.2, m, and n may be the same as defined in Formula 1
above.
[0083] R.sup.4 and R.sup.5 may be each independently selected from
the group consisting of hydrogen; deuterium; tritium; halogen; a
C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60
heterocyclic group containing at least one heteroatom selected from
the group consisting of O, N, S, Si, and P; a fused ring formed by
a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic
ring; a C.sub.1-C.sub.50 alkyl group; a C.sub.2-C.sub.20 alkenyl
group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxy
group; and a C.sub.6-C.sub.30 aryloxy group, or the adjacent groups
may be optionally linked together to form at least one ring.
Herein, the group(s) not forming a ring may be the same as defined
in the above.
[0084] X may be O, S or C(R')(R''), and R' and R'' may be the same
as defined in the structural formula of Ar.sup.1 above. This is, R'
and R'' may be each independently selected from the group
consisting of hydrogen; deuterium; tritium; a C.sub.6-C.sub.20 aryl
group; a C.sub.1-C.sub.20 alkyl group; and a C.sub.2-C.sub.20
alkenyl group. Further, R' and R'' may be optionally linked
together to form a spiro compound with the carbon to which they are
attached.
[0085] The Formula 1 may be represented by the following
formula:
##STR00014##
[0086] In Formula 21 above, the symbols are defined as the same in
Formula 1 above. For example, R.sup.1, R.sup.2, m, n, Ar.sup.1,
Ar.sup.3, L and the like may be the same as defined in Formula 1
above. Ar.sup.4 may be the same as defined in the structural
formula of Ar.sup.2 above. This is, Ar.sup.4 may be selected from
the group consisting of a C.sub.6-C.sub.60 aryl group; a fluorenyl
group; and a C.sub.2-C.sub.60 heterocyclic group containing at
least one heteroatom selected from the group consisting of O, N, S,
Si, and P.
[0087] R.sup.6, R.sup.7, a, and b may be the same as defined in the
structure of Ar.sup.2 above. This is, R.sup.6 and R.sup.7 may be
each independently selected from the group consisting of i)
deuterium; halogen; a C.sub.6-C.sub.60 aryl group; a fluorenyl
group; a C.sub.2-C.sub.60 heterocyclic group containing at least
one heteroatom selected from the group consisting of O, N, S, Si,
and P; a fused ring formed by a C.sub.3-C.sub.60 aliphatic ring and
a C.sub.6-C.sub.60 aromatic ring; a C.sub.1-C.sub.50 alkyl group; a
C.sub.2-C.sub.20 alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a
C.sub.1-C.sub.30 alkoxy group; a C.sub.6-C.sub.30 aryloxy group;
and -L'-N(R.sup.a)(R.sup.b), herein, L' may be selected from the
group consisting of single bond; a C.sub.6-C.sub.60 arylene group;
a fluorenylene group; a fused ring formed by a C.sub.3-C.sub.60
aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; and a
C.sub.2-C.sub.60 heterocyclic group containing at least one
heteroatom selected from the group consisting of O, N, S, Si, and
P, and R.sup.a and R.sup.b may be each independently selected from
the group consisting of a C.sub.6-C.sub.60 aryl group; a fluorenyl
group; a fused ring formed by a C.sub.3-C.sub.60 aliphatic ring and
a C.sub.6-C.sub.60 aromatic ring; and a C.sub.2-C.sub.60
heterocyclic group containing at least one heteroatom selected from
the group consisting of O, N, S, Si, and P. ii) adjacent groups of
R.sup.6 and R.sup.7 may be optionally linked together to form at
least one ring, and the group of R.sup.6s and R.sup.7s not forming
a ring may be the same as defined in above i).
[0088] Further, a may be an integer of 0 to 4, and R.sup.6 may be
same or different each other when a is 2 or more, b may be an
integer of 0 to 3, and R.sup.7 may be same or different each other
when b is 2 or more.
[0089] More specifically, the above Formula 21 may represent any
one of the following formulas:
##STR00015##
[0090] In Formulas 22 and 23, the symbols are defined as the same
in Formula 1 or 21 above.
[0091] More specifically, the compounds represented by Formulas 1
to 21 may be any one of the following compounds.
##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020##
##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025##
##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030##
##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035##
##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040##
##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045##
##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050##
##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055##
##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060##
##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065##
##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070##
##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075##
##STR00076##
[0092] In another aspect of the present invention, a compound for
an organic electric element represented by Formula 1 above is
provided.
[0093] In another aspect of the present invention, an organic
electric element comprising the compound represented by Formula 1
above is provided.
[0094] The organic electric element can comprise a first electrode,
a second electrode, and an organic material layer disposed between
the first electrode and the second electrode. The organic material
layer can comprise the compound represented by Formula 1. The
compound represented Formula 1 can be contained in at least one
layer of a hole injection layer, a hole transport layer, an
emission-auxiliary layer and a light emitting layer of the organic
material layer. That is, the compound represented by Formula 1 may
be used as a material in the hole injection layer, a material in
the hole transport layer, a material in the emission-auxiliary
layer, or a material in the light emitting layer, preferably, as a
material a hole transport layer and/or an emission-auxiliary
layer.
[0095] Specifically, the organic electric element comprising the
organic material layer comprising at least one of the compounds
represented by Formula 2 to 23 is provided, and more specifically,
the organic electric element comprising the organic material layer
comprising at least one of the compounds P1-1 to P1-112, P2-1 to
P2-112, P3-1 to P3-39 and P4-1 to P4-36 is provided.
[0096] Furthermore, the compounds comprising of an organic material
layer can be one kind or two or more different kinds of the
compounds represented by Formula 1 above. For example, a hole
transport layer and/or an emission-auxiliary layer of an organic
material layer may be formed as a single kind, 2 or more different
kinds of individual compounds P1-1 or P1-2, or 3 or more different
kinds of compound P1-1, P1-2 and P1-3.
[0097] In another aspect of the present invention, the present
invention provides an organic electric element further including at
least a layer to improve luminescence efficiency which is formed on
at least one of the sides the first and second electrodes, which is
opposite to the organic material layer.
[0098] Hereinafter, Synthesis Examples of the inventive compound
represented by Formula 1 above and Preparation Examples of an
organic electric element will be described in detail by way of
example. However, the following examples are only for illustrative
purposes and are not intended to limit the scope of the
invention.
Synthesis Example
[0099] The final product of the present invention can be
synthesized by reaction of Sub 1 and Sub 2 as illustrated in the
following Reaction Scheme 1, but the present invention is not
limited to the following examples.
##STR00077##
I. Synthesis Example of Sub 1
[0100] Sub 1 of the Reaction Scheme 1 can be synthesized according
to, but not limited to, the following Reaction Scheme 2.
##STR00078## ##STR00079##
1. Synthesis Example of Sub 1-1
(1) Synthesis of Sub 1-I-1
##STR00080##
[0102] Phenylboronic acid (76.84 g, 630.2 mmol) was dissolved in
THF (2780 ml) in a round bottom flask. Then,
4-bromo-1-iodo-2-nitrobenzene (309.96 g, 945.3 mmol),
Pd(PPh.sub.3).sub.4 (36.41 g, 31.5 mmol), K.sub.2CO.sub.3 (261.3 g,
1890.6 mmol) and water (1390 ml) were added into the round bottom
flask, and the mixture was stirred at 80.degree. C. After the
completion of the reaction, the reaction product was extracted with
CH.sub.2Cl.sub.2 and water. The extracted organic layer was dried
over MgSO.sub.4 and concentrated. The concentrated resultant was
separated by silica gel column chromatography, and was then
recrystallized, whereby a compound Sub 1-I-1 was obtained in an
amount of 122.68 g in 70% yield.
(2) Synthesis of Sub 1-II-1
##STR00081##
[0104] The compound Sub 1-I-1 (122.68 g, 441.1 mmol) obtained above
was dissolved in o-dichlorobenzene (1810 ml) in a round bottom
flask. Then, triphenylphosphine (289.26 g, 1102.8 mmol) was added
into the round bottom flask, and the mixture was stirred at
200.degree. C. After the completion of the reaction,
o-dichlorobenzene from the reaction product was removed by
distillation and the reaction product was extracted with
CH.sub.2Cl.sub.2 and water. The extracted organic layer was dried
over MgSO.sub.4 and concentrated. The concentrated resultant was
separated by silica gel column chromatography, and was then
recrystallized, whereby a compound Sub 1-II-1 was obtained in an
amount of 80.34 g in 74% yield.
(3) Synthesis of Sub 1-III-1
##STR00082##
[0106] The compound Sub 1-II-1 (80.34 g, 326.5 mmol) obtained above
was dissolved in nitrobenzene (653 ml) in a round bottom flask.
Then, iodobenzene (99.9 g, 489.7 mmol), Na.sub.2SO.sub.4 (46.37 g,
326.5 mmol), K.sub.2CO.sub.3 (45.12 g, 326.5 mmol) and Cu (6.22 g,
97.9 mmol) were added into the round bottom flask, and the mixture
was stirred at 200.degree. C. After the completion of the reaction,
nitrobenzene from the reaction product was removed by distillation
and the reaction product was extracted with CH.sub.2Cl.sub.2 and
water. The extracted organic layer was dried over MgSO.sub.4 and
concentrated. The concentrated resultant was separated by silica
gel column chromatography, and was then recrystallized, whereby a
compound Sub 1-III-1 was obtained in an amount of 76.78 g in 73%
yield.
(4) Synthesis of Sub 1-IV-1
##STR00083##
[0108] The compound Sub 11-III-1 (76.78 g, 238.3 mmol) obtained
above was dissolved in DMF in a round bottom flask. Then,
Bis(pinacolato)diboron (66.57 g, 262.1 mmol), Pd(dppf)Cl2 (5.84 g,
7.1 mmol) and KOAc (70.16 g, 714.9 mmol) were added into the round
bottom flask, and the mixture was stirred at 90.degree. C. After
the completion of the reaction, DMF from the reaction product was
removed by distillation and the reaction product was extracted with
CH.sub.2Cl.sub.2 and water. The extracted organic layer was dried
over MgSO.sub.4 and concentrated. The concentrated resultant was
separated by silica gel column chromatography, and was then
recrystallized, whereby a compound Sub 1-IV-1 was obtained in an
amount of 73.92 g in 84% yield.
(5) Synthesis of Sub 1-1
##STR00084##
[0110] The compound Sub 1-IV-1 (73.92 g, 200.2 mmol) obtained above
was dissolved in THF (880 ml) in a round bottom flask. Then,
1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), Pd(PPh.sub.3).sub.4
(11.6 g, 10 mmol), K.sub.2CO.sub.3 (83 g, 600.6 mmol) and water
(440 mL) were added into the round bottom flask, and the mixture
was stirred at 80.degree. C. After the completion of the reaction,
the reaction product was extracted with CH.sub.2Cl.sub.2 and water.
The extracted organic layer was dried over MgSO.sub.4 and
concentrated. The concentrated resultant was separated by silica
gel column chromatography, and was then recrystallized, whereby a
compound Sub 1-1 was obtained in an amount of 55.8 g in 70%
yield.
2. Synthesis Examples of Sub 1-7
(1) Synthesis of Sub 1-I-7
##STR00085##
[0112] The compound Sub 1-I-7 was synthesized by using
(4-(dibenzo[b,d]thiophen-2-yl)phenyl)boronic acid (95.8 g, 315.1
mmol), THF (1390 ml), 4-bromo-1-iodo-2-nitrobenzene (155 g, 472.7
mmol), Pd(PPh.sub.3).sub.4 (18.2 g, 15.8 mmol), K.sub.2CO.sub.3
(130.7 g, 945.3 mmol) and water (695 ml) in the same manner as
described in the synthesis method of the compound Sub 1-I-1 above,
whereby a compound Sub 1-I-7 was obtained in an amount of 103 g in
71% yield.
(2) Synthesis of Sub 1-II-7
##STR00086##
[0114] The compound Sub 1-II-7 was synthesized by using Sub 1-I-7
(103 g, 223.7 mmol), o-dichlorobenzene (917 ml), and
triphenylphosphine (146.7 g, 559.3 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-II-1 above,
whereby a compound Sub 1-II-7 was obtained in an amount of 69 g in
72% yield.
(3) Synthesis of Sub 1-III-7
##STR00087##
[0116] The compound Sub 1-III-7 was synthesized by using Sub 1-II-7
(69 g, 161.1 mmol), nitrobenzene (322 ml), iodobenzene (49.4 g, 242
mmol), Na.sub.2SO.sub.4 (22.9 g, 161.1 mmol), K.sub.2CO.sub.3 (22.3
g, 161.1 mmol) and Cu (3.1 g, 48.3 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-III-1
above, whereby a compound Sub 1-III-7 was obtained in an amount of
57 g in 70% yield.
(4) Synthesis of Sub 1-IV-7
##STR00088##
[0118] The compound Sub 1-IV-7 was synthesized by using Sub 1-III-7
(57 g, 113 mmol), DMF (712 ml), Bis(pinacolato)diboron (31.6 g,
124.3 mmol), Pd(dppf)Cl.sub.2 (2.8 g, 3.4 mmol) and KOAc (33.3 g,
339 mmol) in the same manner as described in the synthesis method
of the compound Sub 1-IV-1 above, whereby a compound Sub 1-IV-7 was
obtained in an amount of 49.2 g in 79% yield.
(5) Synthesis of Sub 1-7
##STR00089##
[0120] The compound Sub 1-7 was synthesized by using Sub 1-IV-7
(49.2 g, 89.2 mmol), 1-bromo-2-iodobenzene (39.9 g, 134 mmol),
Pd(PPh.sub.3).sub.4 (5.2 g, 4.5 mmol), K.sub.2CO.sub.3 (37 g, 268
mmol), THF (392 ml) and water (196 ml) in the same manner as
described in the synthesis method of the compound Sub 1-1 above,
whereby a compound Sub 1-7 was obtained in an amount of 35.7 g in
69% yield.
3. Synthesis Examples of Sub 1-13
(1) Synthesis of Sub 1-III-13
##STR00090##
[0122] The compound Sub 1-III-13 was synthesized by using Sub
1-II-1 (70 g, 284.4 mmol), nitrobenzene (570 ml),
2-iodo-9,9-diphenyl-9H-fluorene (189.6 g, 426.7 mmol),
Na.sub.2SO.sub.4 (40.4 g, 284.4 mmol), K.sub.2CO.sub.3 (39.3 g,
284.4 mmol) and Cu (5.42 g, 85.3 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-III-1
above, whereby a compound Sub 1-III-13 was obtained in an amount of
108.8 g in 68% yield.
(2) Synthesis of Sub 1-IV-13
##STR00091##
[0124] The compound Sub 1-IV-13 was synthesized by using (108.8 g,
193.4 mmol), DMF (1220 ml), Bis(pinacolato)diboron (54.0 g, 212.76
mmol), Pd(dppf)Cl.sub.2 (4.73 g, 5.8 mmol) and KOAc (56.94 g, 580.3
mmol) in the same manner as described in the synthesis method of
the compound Sub 1-IV-1 above, whereby a compound Sub 1-IV-13 was
obtained in an amount of 86.1 g in 73% yield.
(3) Synthesis of Sub 1-13
##STR00092##
[0126] The compound Sub 1-13 was synthesized by using Sub 1-IV-13
(86.1 g, 141.2 mmol), THF (620 ml), 1-bromo-2-iodobenzene (59.9 g,
211.9 mmol), Pd(PPh.sub.3).sub.4 (8.2 g, 7.06 mmol),
K.sub.2CO.sub.3 (58.6 g, 423.7 mmol) and water (310 ml) in the same
manner as described in the synthesis method of the compound Sub 1-1
above, whereby a compound Sub 1-13 was obtained in an amount of
58.6 g in 65% yield.
4. Synthesis of Sub 1-14
(1) Synthesis of Sub 1-III-14
##STR00093##
[0128] The compound Sub 1-III-14 was synthesized by using Sub
1-II-1 (63 g, 255.9 mmol), nitrobenzene (512 ml),
3-iodo-9,9-diphenyl-9H-fluorene (170.6 g, 383.9 mmol),
Na.sub.2SO.sub.4 (36.4 g, 256 mmol), K.sub.2CO.sub.3 (35.4 g, 256
mmol) and Cu (4.88 g, 76.8 mmol) in the same manner as described in
the synthesis method of the compound Sub 1-III-1 above, whereby a
compound Sub 1-III-14 was obtained in an amount of 99.3 g in 69%
yield.
(2) Synthesis of Sub 1-IV-14
##STR00094##
[0130] The compound Sub 1-IV-14 was synthesized by using Sub
1-III-14 (99.3 g, 193.4 mmol), DMF (1110 ml),
Bis(pinacolato)diboron (49.3 g, 194.2 mmol), Pd(dppf)Cl.sub.2 (4.32
g, 5.3 mmol) and KOAc (52 g, 529.6 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-IV-1 above,
whereby a compound Sub 1-IV-14 was obtained in an amount of 80.7 g
in 75% yield.
(3) Synthesis of Sub 1-14
##STR00095##
[0132] The compound Sub 1-14 was synthesized by using Sub 1-IV-14
(80.7 g, 132.3 mmol), THF (582 ml), 1-bromo-2-iodobenzene (56.2 g,
198.6 mmol), Pd(PPh.sub.3).sub.4 (7.65 g, 6.62 mmol),
K.sub.2CO.sub.3 (54.9 g, 397.2 mmol) and water (291 ml) in the same
manner as described in the synthesis method of the compound Sub 1-1
above, whereby a compound Sub 1-14 was obtained in an amount of
52.4 g in 62% yield.
5. Synthesis of Sub 1-17
(1) Synthesis of Sub 1-III-17
##STR00096##
[0134] The compound Sub 1-III-17 was synthesized by using Sub
1-II-1 (60 g, 244 mmol), nitrobenzene (487 ml),
5'-iodo-1,1':3',1''-terphenyl (130.3 g, 365.7 mmol),
Na.sub.2SO.sub.4 (34.6 g, 244 mmol), K.sub.2CO.sub.3 (33.7 g, 244
mmol) and Cu (4.65 g, 73.1 mmol) in the same manner as described in
the synthesis method of the compound Sub 1-III-1 above, whereby a
compound Sub 1-III-17 was obtained in an amount of 82.1 g in 71%
yield.
(2) Synthesis of Sub 1-IV-17
##STR00097##
[0136] The compound Sub 1-IV-17 was synthesized by using Sub
1-III-17 (82.1 g, 173.1 mmol), DMF (1090 ml),
Bis(pinacolato)diboron (48.3 g, 190.4 mmol), Pd(dppf)Cl.sub.2 (4.24
g, 5.2 mmol) and KOAc (51 g, 519.2 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-IV-1 above,
whereby a compound Sub 1-IV-17 was obtained in an amount of 65.9 g
in 73% yield.
(3) Synthesis of Sub 1-17
##STR00098##
[0138] The compound Sub 1-17 was synthesized by using Sub 1-IV-17
(65.9 g, 126.4 mmol), THF (556 ml), 1-bromo-2-iodobenzene (53.8 g,
190 mmol), Pd(PPh.sub.3).sub.4 (7.3 g, 6.32 mmol), K.sub.2CO.sub.3
(52.4 g, 319.1 mmol) and water (278 ml) in the same manner as
described in the synthesis method of the compound Sub 1-1 above,
whereby a compound Sub 1-17 was obtained in an amount of 45.2 g in
65% yield.
6. Synthesis of Sub 1-32
(1) Synthesis of Sub 1-I-32
##STR00099##
[0140] The compound Sub 1-I-32 was synthesized by using
naphthalen-1-ylboronic acid (70 g, 407 mmol), THF (1790 ml),
4-bromo-1-iodo-2-nitrobenzene (200 g, 610.5 mmol),
Pd(PPh.sub.3).sub.4 (23.5 g, 20.35 mmol), K.sub.2CO.sub.3 (168.8 g,
1221 mmol) and water (895 ml) in the same manner as described in
the synthesis method of the compound Sub 1-I-1 above, whereby a
compound Sub 1-I-32 was obtained in an amount of 94.8 g in 71%
yield.
(2) Synthesis of Sub 1-II-32
##STR00100##
[0142] The compound Sub 1-II-32 was synthesized by using Sub 1-I-32
(94.8 g, 288.9 mmol), o-dichlorobenzene (1184 ml) and
triphenylphosphine (189.4 g, 722.2 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-II-1 above,
whereby a compound Sub 1-II-32 was obtained in an amount of 61.2 g
in 75% yield.
(3) Synthesis of Sub 1-III-32
##STR00101##
[0144] The compound Sub 1-III-32 was synthesized by using Sub
1-II-32 (61.2 g, 206.6 mmol), nitrobenzene (413 ml),
2-iodo-9,9-diphenyl-9H-fluorene (137.7 g, 310 mmol),
Na.sub.2SO.sub.4 (29.35 g, 206.6 mmol), K.sub.2CO.sub.3 (28.6 g,
206.6 mmol) and Cu (3.9 g, 62 mmol) in the same manner as described
in the synthesis method of the compound Sub 1-III-1 above, whereby
a compound Sub 1-III-32 was obtained in an amount of 89.86 g in 71%
yield.
(4) Synthesis of Sub 1-IV-32
##STR00102##
[0146] The compound Sub 1-IV-32 was synthesized by using Sub
1-III-32 (89.86 g, 146.7 mmol), DMF (924 ml),
Bis(pinacolato)diboron (41 g, 161.4 mmol), Pd(dppf)Cl.sub.2 (3.59
g, 4.4 mmol) and KOAc (43.2 g, 440.1 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-IV-1 above,
whereby a compound Sub 1-IV-32 was obtained in an amount of 74.5 g
in 77% yield.
(5) Synthesis of Sub 1-32
##STR00103##
[0148] The compound Sub Sub 1-32 was synthesized by using Sub
1-IV-32 (74.5 g, 112.9 mmol), THF (496 ml), 2-iodobenzene (47.9 g,
169.4 mmol), Pd(PPh.sub.3).sub.4 (6.53 g, 5.65 mmol),
K.sub.2CO.sub.3 (46.8 g, 338.8 mmol) and water (248 ml) in the same
manner as described in the synthesis method of the compound Sub 1-1
above, whereby a compound Sub Sub 1-32 was obtained in an amount of
47.4 g in 61% yield.
7. Synthesis of 1-34
(1) Synthesis of Sub 1-I-34
##STR00104##
[0150] The compound Sub 1-I-34 was synthesized by using
naphthalen-2-ylboronic acid (70 g, 407 mmol), THF (1790 ml),
4-bromo-1-iodo-2-nitrobenzene (200 g, 610.5 mmol),
Pd(PPh.sub.3).sub.4 (23.5 g, 20.35 mmol), K.sub.2CO.sub.3 (168.8 g,
1221 mmol) and water (895 ml) in the same manner as described in
the synthesis method of the compound Sub 1-I-1 above, whereby a
compound Sub 1-I-34 was obtained in an amount of 97.5 g in 73%
yield.
(2) Synthesis of Sub 1-II-34
##STR00105##
[0152] The compound Sub 1-II-34 was synthesized by using Sub 1-I-34
(97.5 g, 297.1 mmol), o-dichlorobenzene (1220 ml) and
triphenylphosphine (194.8 g, 742.8 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-II-1 above,
whereby a compound Sub 1-II-34 was obtained in an amount of 65.1 g
in 74% yield.
(3) Synthesis of Sub 1-III-34
##STR00106##
[0154] The compound Sub 1-III-34 was synthesized by using Sub
1-II-34 (65.1 g, 220 mmol), nitrobenzene (440 ml),
3-iodo-9,9-diphenyl-9H-fluorene (146.5 g, 330 mmol),
Na.sub.2SO.sub.4 (31.2 g, 220 mmol), K.sub.2CO.sub.3 (30.4 g, 220
mmol) and Cu (4.2 g, 66 mmol) in the same manner as described in
the synthesis method of the compound Sub 1-III-1 above, whereby a
compound Sub 1-III-34 was obtained in an amount of 95.6 g in 71%
yield.
(4) Synthesis of Sub 1-IV-34
##STR00107##
[0156] The compound Sub 1-IV-34 was synthesized by using Sub
1-III-34 (95.6 g, 156.1 mmol), DMF (980 ml), Bis(pinacolato)diboron
(43.6 g, 171.7 mmol), Pd(dppf)Cl.sub.2 (3.82 g, 4.7 mmol) and KOAc
(46 g, 468.2 mmol) in the same manner as described in the synthesis
method of the compound Sub 1-IV-1 above, whereby a compound Sub
1-IV-34 was obtained in an amount of 77.2 g in 75% yield.
(5) Synthesis of Sub 1-34
##STR00108##
[0158] The compound Sub 1-34 was synthesized by using Sub 1-IV-34
(77.2 g, 117 mmol), THF (510 ml), 1-bromo-2-(49.7 g, 175.6 mmol),
Pd(PPh.sub.3).sub.4 (6.76 g, 5.85 mmol), K.sub.2CO.sub.3 (48.5 g,
351 mmol) and water (255 ml) in the same manner as described in the
synthesis method of the compound Sub 1-1 above, whereby a compound
Sub 1-34 was obtained in an amount of 49.1 g in 63% yield.
8. Synthesis of 1-35
(1) Synthesis of Sub 1-I-35
##STR00109##
[0160] The compound Sub 1-I-35 was synthesized by using
phenanthren-9-ylboronic acid (70 g, 315.2 mmol), THF (1388 ml),
4-bromo-1-iodo-2-nitrobenzene (155.1 g, 472.9 mmol),
Pd(PPh.sub.3).sub.4 (18.2 g, 15.8 mmol), K.sub.2CO.sub.3 (130.7 g,
945.7 mmol) and water (694 ml) in the same manner as described in
the synthesis method of the compound Sub 1-I-1 above, whereby a
compound Sub 1-I-35 was obtained in an amount of 85.8 g in 72%
yield.
(2) Synthesis of Sub 1-II-35
##STR00110##
[0162] The compound Sub 1-II-35 was synthesized by using Sub 1-I-35
(85.8 g, 226.9 mmol), o-dichlorobenzene (930 ml) and
triphenylphosphine (148.8 g, 567.1 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-II-1 above,
whereby a compound Sub 1-II-35 was obtained in an amount of 60.5 g
in 77% yield.
(3) Synthesis of Sub 1-III-35
##STR00111##
[0164] The compound Sub 1-III-35 was synthesized by using Sub
1-II-35 (60.5 g, 174.7 mmol), nitrobenzene (350 ml),
3-iodo-9,9-diphenyl-9H-fluorene (116.5 g, 262.1 mmol),
Na.sub.2SO.sub.4 (24.8 g, 174.7 mmol), K.sub.2CO.sub.3 (24.2 g,
174.7 mmol) and Cu (3.33 g, 52.4 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-III-1
above, whereby a compound Sub 1-III-35 was obtained in an amount of
84.5 g in 73% yield.
(4) Synthesis of Sub 1-IV-35
##STR00112##
[0166] The compound Sub 1-IV-35 was synthesized by using Sub
1-III-35 (84.5 g, 127.5 mmol), DMF (854 ml), Bis(pinacolato)diboron
(35.6 g, 140.3 mmol), Pd(dppf)Cl.sub.2 (3.12 g, 3.82 mmol) and KOAc
(37.5 g, 382.5 mmol) in the same manner as described in the
synthesis method of the compound Sub 1-IV-1 above, whereby a
compound Sub 1-IV-35 was obtained in an amount of 70.6 g in 78%
yield.
(5) Synthesis of Sub 1-35
##STR00113##
[0168] The compound Sub 1-IV-35 (70.6 g, 99.5 mmol), THF (438 ml),
1-bromo-2-iodobenzene (42.2 g, 149.2 mmol), Pd(PPh.sub.3).sub.4
(5.75 g, 4.97 mmol), K.sub.2CO.sub.3 (41.2 g, 298.4 mmol) and water
(219 ml) in the same manner as described in the synthesis method of
the compound Sub 1-1 above, whereby a compound Sub 1-35 was
obtained in an amount of 45.6 g in 62% yield.
9. Synthesis of Sub 1-44
(1) Synthesis of Sub 1-III-44
##STR00114##
[0170] The compound Sub 1-III-44 was synthesized by using Sub
1-II-1 (60 g, 244 mmol), nitrobenzene (487 ml),
2-iododibenzo[b,d]furan (107.6 g, 365.7 mmol), Na.sub.2SO.sub.4
(34.6 g, 244 mmol), K.sub.2CO.sub.3 (33.7 g, 244 mmol) and Cu (4.65
g, 73.1 mmol) in the same manner as described in the synthesis
method of the compound Sub 1-III-1 above, whereby a compound Sub
1-III-44 was obtained in an amount of 68.4 g in 68% yield.
(2) Synthesis of Sub 1-IV-44
##STR00115##
[0172] The compound Sub 1-IV-44 was synthesized by using Sub
1-III-44 (68.4 g, 166 mmol), DMF (1045 ml), Bis(pinacolato)diboron
(46.3 g, 182.5 mmol), Pd(dppf)Cl.sub.2 (4.06 g, 5 mmol) and KOAc
(48.8 g, 497.7 mmol) in the same manner as described in the
synthesis method of the compound Sub 1-IV-1 above, whereby a
compound Sub 1-IV-44 was obtained in an amount of 56.4 g in 74%
yield.
(3) Synthesis of Sub 1-44
##STR00116##
[0174] The compound Sub 1-44 was synthesized by using Sub 1-IV-44
(56.4 g, 122.8 mmol), THF (540 ml), 1-bromo-2-iodobenzene (52.1 g,
184 mmol), Pd(PPh.sub.3).sub.4 (7.1 g, 6.14 mmol), K.sub.2CO.sub.3
(50.9 g, 368.4 mmol) and water (270 ml) in the same manner as
described in the synthesis method of the compound Sub 1-1 above,
whereby a compound Sub 1-44 was obtained in an amount of 17.9 g in
65% yield.
10. Synthesis of Sub 1-54
(1) Synthesis of Sub 1-III-54
##STR00117##
[0176] The compound Sub 1-III-54 was synthesized by using Sub
1-II-1 (50 g, 203.2 mmol), nitrobenzene (406 ml),
4-iodo-1,1'-biphenyl(85.4 g, 304.7 mmol), Na.sub.2SO.sub.4 (28.9 g,
203.2 mmol), K.sub.2CO.sub.3 (28.1 g, 203.2 mmol) and Cu (3.87 g,
61 mmol) in the same manner as described in the synthesis method of
the compound Sub 1-III-1 above, whereby a compound Sub 1-III-54 was
obtained in an amount of 54.2 g in 68% yield.
(2) Synthesis of Sub 1-IV-54
##STR00118##
[0178] The compound Sub 1-IV-54 was synthesized by using Sub
1-III-54 (54.2 g, 136.1 mmol), DMF (857 ml), Bis(pinacolato)diboron
(38.0 g, 150 mmol), Pd(dppf)Cl.sub.2 (3.33 g, 4.1 mmol) and KOAc
(40.1 g, 408 mmol) in the same manner as described in the synthesis
method of the compound Sub 1-IV-1 above, whereby a compound Sub
1-IV-54 was obtained in an amount of 42.4 g in 70% yield.
(3) Synthesis of Sub 1-54
##STR00119##
[0180] The compound Sub 1-54 was synthesized by using Sub 1-IV-54
(42.4 g, 95.2 mmol), THF (418 ml), 1-bromo-3-iodobenzene (40.4 g,
142.8 mmol), Pd(PPh.sub.3).sub.4 (5.5 g, 4.76 mmol),
K.sub.2CO.sub.3 (39.5 g, 285.6 mmol) and water (209 ml) in the same
manner as described in the synthesis method of the compound Sub 1-1
above, whereby a compound Sub 1-54 was obtained in an amount of
30.7 g in 68% yield.
11. Synthesis of Sub 1-66
(1) Synthesis of Sub 1-III-66
##STR00120##
[0182] The compound Sub 1-III-66 was synthesized by using Sub
1-II-1 (50 g, 203.2 mmol), nitrobenzene (406 ml),
1-iodo-9,9-diphenyl-9H-fluorene (135.4 g, 305 mmol),
Na.sub.2SO.sub.4 (28.9 g, 203.2 mmol), K.sub.2CO.sub.3 (28.1 g,
203.2 mmol) and Cu (3.87 g, 61 mmol) in the same manner as
described in the synthesis method of the compound Sub 1-III-1
above, whereby a compound Sub 1-III-66 was obtained in an amount of
70.9 g in 62% yield.
(2) Synthesis of Sub 1-IV-66
##STR00121##
[0184] The compound Sub 1-IV-66 was synthesized by using Sub
1-III-66 (70.9 g, 126 mmol), DMF (794 ml), Bis(pinacolato)diboron
(35.2 g, 138.7 mmol), Pd(dppf)Cl.sub.2 (3.09 g, 3.78 mmol) and KOAc
(37.11 g, 378.1 mmol) in the same manner as described in the
synthesis method of the compound Sub 1-IV-1 above, whereby a
compound Sub 1-IV-66 was obtained in an amount of 51.5 g in 67%
yield.
(3) Synthesis of Sub 1-66
##STR00122##
[0186] The compound Sub Sub 1-66 was synthesized by using Sub
1-IV-66 (51.5 g, 84.5 mmol), THF (370 ml), 1-bromo-3-iodobenzene
(35.8 g, 126.7 mmol), Pd(PPh.sub.3).sub.4 (4.88 g, 4.22 mmol),
K.sub.2CO.sub.3 (35.03 g, 253.5 mmol) and water (185 ml) in the
same manner as described in the synthesis method of the compound
Sub 1-1 above, whereby a compound Sub Sub 1-66 was obtained in an
amount of 33.5 g in 62% yield.
12. Synthesis of Sub 1-103
##STR00123##
[0188] The compound Sub 1-103 was synthesized by Sub 1-IV-1 (31.2
g, 84.5 mmol), THF (370 mL), 3-bromo-5-iodo-1,1'-biphenyl(46.8 g,
126.7 mmol), Pd(PPh.sub.3).sub.4 (4.88 g, 4.22 mmol),
K.sub.2CO.sub.3 (35.03 g, 253.5 mmol) and water (185 mL) in the
same manner as described in the synthesis method of the compound
Sub 1-1 above, whereby a compound Sub 1-103 was obtained in an
amount of 26.1 g in 65% yield.
13. Synthesis of Sub 1-115
##STR00124##
[0190] The compound Sub 1-115 was synthesized by Sub 1-IV-1 (31.2
g, 84.5 mmol), THF (370 mL), 3-bromo-5-iodo-1,1'-biphenyl(46.8 g,
126.7 mmol), Pd(PPh.sub.3).sub.4 (4.88 g, 4.22 mmol),
K.sub.2CO.sub.3 (35.03 g, 253.5 mmol) and water (185 mL) in the
same manner as described in the synthesis method of the compound
Sub 1-1 above, whereby a compound Sub 1-115 was obtained in an
amount of 24.5 g in 61% yield.
[0191] Examples of Sub 1 compounds include, but are not limited to,
the following compounds, and FD-MS (Field Desorption-Mass
Spectrometry) data of the compounds are given in Table 1 below.
##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129##
##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134##
##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139##
##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144##
##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149##
##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154##
##STR00155##
TABLE-US-00001 TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z =
397.05(C.sub.24H.sub.16BrN = 398.29) Sub 1-2 m/z =
447.06(C.sub.28H.sub.18BrN = 448.35) Sub 1-3 m/z =
473.08(C.sub.30H.sub.20BrN = 474.39) Sub 1-4 m/z =
447.06(C.sub.28H.sub.18BrN = 448.35) Sub 1-5 m/z =
473.08(C.sub.30H.sub.20BrN = 474.39) Sub 1-6 m/z =
473.08(C.sub.30H.sub.20BrN = 474.39) Sub 1-7 m/z =
579.07(C.sub.36H.sub.22BrNS = 580.54) Sub 1-8 m/z =
476.06(C.sub.27H.sub.17BrN.sub.4 = 477.35) Sub 1-9 m/z =
437.08(C.sub.27H.sub.20BrN = 438.36) Sub 1-10 m/z =
600.12(C.sub.39H.sub.25BrN.sub.2 = 601.53) Sub 1-11 m/z =
473.08(C.sub.30H.sub.20BrN = 474.39) Sub 1-12 m/z =
601.12(C.sub.38H.sub.24BrN.sub.3 = 602.52) Sub 1-13 m/z =
637.14(C.sub.43H.sub.28BrN = 638.59) Sub 1-14 m/z =
637.14(C.sub.43H.sub.28BrN = 638.59) Sub 1-15 m/z =
637.14(C.sub.43H.sub.28BrN = 638.59) Sub 1-16 m/z =
637.14(C.sub.43H.sub.28BrN = 638.59) Sub 1-17 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-18 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-19 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-20 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-21 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-22 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-23 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-24 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-25 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-26 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-27 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-28 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-29 m/z =
559.2(C.sub.36H.sub.14D.sub.10BrN = 560.6) Sub 1-30 m/z = 559.17
(C.sub.36H.sub.14D.sub.10BrN = 560.6) Sub 1-31 m/z =
554.1(C.sub.36H.sub.19D.sub.5BrN = 555.52) Sub 1-32 m/z =
687.16(C.sub.47H.sub.30BrN = 688.65) Sub 1-33 m/z =
687.16(C.sub.47H.sub.30BrN = 688.65) Sub 1-34 m/z =
687.16(C.sub.47H.sub.30BrN = 688.65) Sub 1-35 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-36 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-37 m/z =
687.16(C.sub.47H.sub.30BrN = 688.65) Sub 1-38 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-39 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-40 m/z =
503.03(C.sub.30H.sub.18BrNS = 504.44) Sub 1-41 m/z =
503.03(C.sub.30H.sub.18BrNS = 504.44) Sub 1-42 m/z =
503.03(C.sub.30H.sub.18BrNS = 504.44) Sub 1-43 m/z =
503.03(C.sub.30H.sub.18BrNS = 504.44) Sub 1-44 m/z =
487.06(C.sub.30H.sub.18BrNO = 488.37) Sub 1-45 m/z =
487.1(C.sub.30H.sub.18BrNO = 488.37) Sub 1-46 m/z =
487.06(C.sub.30H.sub.18BrNO = 488.37) Sub 1-47 m/z =
487.1(C.sub.30H.sub.18BrNO = 488.37) Sub 1-48 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-49 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-50 m/z =
553.05(C.sub.34H.sub.20BrNS = 554.50) Sub 1-51 m/z =
537.07(C.sub.34H.sub.20BrNO = 538.43) Sub 1-52 m/z =
397.05(C.sub.24H.sub.16BrN = 398.29) Sub 1-53 m/z =
447.06(C.sub.28H.sub.18BrN = 448.35) Sub 1-54 m/z =
473.08(C.sub.30H.sub.20BrN = 474.39) Sub 1-55 m/z =
447.06(C.sub.28H.sub.18BrN = 448.35) Sub 1-56 m/z =
473.08(C.sub.30H.sub.20BrN = 474.39) Sub 1-57 m/z =
473.08(C.sub.30H.sub.20BrN = 474.39) Sub 1-58 m/z =
579.07(C.sub.36H.sub.22BrNS = 580.54) Sub 1-59 m/z =
476.06(C.sub.27H.sub.17BrN.sub.4 = 477.35) Sub 1-60 m/z =
437.08(C.sub.27H.sub.20BrN = 438.36) Sub 1-61 m/z =
600.12(C.sub.39H.sub.25BrN.sub.2 = 601.53) Sub 1-62 m/z =
473.08(C.sub.30H.sub.20BrN = 474.39) Sub 1-63 m/z =
601.12(C.sub.38H.sub.24BrN.sub.3 = 602.52) Sub 1-64 m/z =
637.14(C.sub.43H.sub.28BrN = 638.59) Sub 1-65 m/z =
637.14(C.sub.43H.sub.28BrN = 638.59) Sub 1-66 m/z =
637.14(C.sub.43H.sub.28BrN = 638.59) Sub 1-67 m/z =
637.14(C.sub.43H.sub.28BrN = 638.59) Sub 1-68 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-69 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-70 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-71 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-72 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-73 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-74 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-75 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-76 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-77 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-78 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-79 m/z =
549.11(C.sub.36H.sub.24BrN = 550.49) Sub 1-80 m/z = 559.17
(C.sub.36H.sub.14D.sub.10BrN = 560.6) Sub 1-81 m/z = 559.2
(C.sub.36H.sub.14D.sub.10BrN = 560.6) Sub 1-82 m/z =
554.14(C.sub.36H.sub.19D.sub.5BrN = 555.52) Sub 1-83 m/z =
687.16(C.sub.47H.sub.30BrN = 688.65) Sub 1-84 m/z =
687.16(C.sub.47H.sub.30BrN = 688.65) Sub 1-85 m/z =
687.16(C.sub.47H.sub.30BrN = 688.65) Sub 1-86 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-87 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-88 m/z =
687.16(C.sub.47H.sub.30BrN = 688.65) Sub 1-89 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-90 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-91 m/z =
503.03(C.sub.30H.sub.18BrNS = 504.44) Sub 1-92 m/z =
503.03(C.sub.30H.sub.18BrNS = 504.44) Sub 1-93 m/z =
503.03(C.sub.30H.sub.18BrNS = 504.44) Sub 1-94 m/z =
503.03(C.sub.30H.sub.18BrNS = 504.44) Sub 1-95 m/z =
487.1(C.sub.30H.sub.18BrNO = 488.37) Sub 1-96 m/z =
487.06(C.sub.30H.sub.18BrNO = 488.37) Sub 1-97 m/z =
487.1(C.sub.30H.sub.18BrNO = 488.37) Sub 1-98 m/z =
487.06(C.sub.30H.sub.18BrNO = 488.37) Sub 1-99 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-100 m/z =
737.17(C.sub.51H.sub.32BrN = 738.71) Sub 1-101 m/z =
553.05(C.sub.34H.sub.20BrNS = 554.50) Sub 1-102 m/z =
537.07(C.sub.34H.sub.20BrNO = 538.43) Sub 1-103 m/z =
473.08(C30H20BrN = 474.39) Sub 1-104 m/z = 549.11(C36H24BrN =
550.49) Sub 1-105 m/z = 549.11(C36H24BrN = 550.49) Sub 1-106 m/z =
599.12(C40H26BrN = 600.55) Sub 1-107 m/z = 599.12(C40H26BrN =
600.55) Sub 1-108 m/z = 599.12(C40H26BrN = 600.55) Sub 1-109 m/z =
599.12(C40H26BrN = 600.55) Sub 1-110 m/z = 474.07(C29H19BrN2 =
475.38) Sub 1-111 m/z = 524.09(C33H21BrN2 = 525.44) Sub 1-112 m/z =
525.08(C32H20BrN3 = 526.43) Sub 1-113 m/z = 475.07(C28H18BrN3 =
476.37) Sub 1-114 m/z = 473.08(C30H20BrN = 474.39) Sub 1-115 m/z =
473.08(C30H20BrN = 474.39) Sub 1-116 m/z = 473.08(C30H20BrN =
474.39) Sub 1-117 m/z = 523.09 (C34H22BrN = 524.45) Sub 1-118 m/z =
523.09 (C34H22BrN = 524.45) Sub 1-119 m/z = 549.11(C36H24BrN =
550.49) Sub 1-120 m/z = 549.11(C36H24BrN = 550.49) Sub 1-121 m/z =
599.12(C40H26BrN = 600.55) Sub 1-122 m/z = 599.12(C40H26BrN =
600.55) Sub 1-123 m/z = 599.12(C40H26BrN = 600.55) Sub 1-124 m/z =
599.12(C40H26BrN = 600.55) Sub 1-125 m/z = 474.07(C29H19BrN2 =
475.38) Sub 1-126 m/z = 524.09(C33H21BrN2 = 525.44) Sub 1-127 m/z =
525.08(C32H20BrN3 = 526.43) Sub 1-128 m/z = 475.07(C28H18BrN3 =
476.37)
II. Synthesis Examples of Sub 2
[0192] Sub 2 of the Reaction Scheme 1 can be synthesized according
to, but not limited to, the following Reaction Scheme 48.
##STR00156##
[0193] The synthesis examples of compounds included in Sub 2 are as
below.
1. Synthesis of Sub 2-1
##STR00157##
[0195] Bromobenzene (37.1 g, 236.2 mmol) was dissolved in toluene
(2200 ml) in a round bottom flask. Then, aniline (20 g, 214.8
mmol), Pd.sub.2(dba).sub.3 (9.83 g, 10.7 mmol), P(t-Bu).sub.3 (4.34
g, 21.5 mmol) and NaOt-Bu (62 g, 644.3 mmol) were added into the
round bottom flask, and the mixture was stirred 100.degree. C.
After the completion of the reaction, the reaction product was
extracted with ether and water. The extracted organic layer was
dried over MgSO.sub.4 and concentrated. The concentrated resultant
was separated by silica gel column chromatography, and was then
recrystallized, whereby a compound Sub 2-1 was obtained in an
amount of 28 g in 77% yield.
2. Synthesis of Sub 2-3
##STR00158##
[0197] The compound Sub 2-3 was synthesized by using
3-bromo-1,1'-biphenyl (55.1 g, 236.2 mmol), aniline (20 g, 214.8
mmol), Pd.sub.2(dba).sub.3 (9.83 g, 10.7 mmol), P(t-Bu).sub.3 (4.34
g, 21.5 mmol), NaOt-Bu (62 g, 644.3 mmol) and toluene (2200 ml) in
the same manner as described in the synthesis method of the
compound Sub 2-1 above, whereby a compound Sub 2-3 was obtained in
an amount of 41.1 g in 78% yield.
3. Synthesis of Sub 2-4
##STR00159##
[0199] The compound Sub 2-4 was synthesized by using
4-bromo-1,1'-biphenyl (37.88 g, 162.5 mmol),
[1,1'-biphenyl]-4-amine (25 g, 147.7 mmol), Pd.sub.2(dba).sub.3
(6.76 g, 7.4 mmol), P(t-Bu).sub.3 (3 g, 14.8 mmol) and NaOt-Bu
(66.62 g, 693.2 mmol) in the same manner as described in the
synthesis method of the compound Sub 2-1 above, whereby a compound
Sub 2-4 was obtained in an amount of 35.6 g in 75% yield.
4. Synthesis of Sub 2-7
##STR00160##
[0201] The compound Sub 2-7 was synthesized by using
2-bromonaphthalene (39.8 g, 192.1 mmol), naphthalen-1-amine (25 g,
174.6 mmol), Pd.sub.2(dba).sub.3 (8.0 g, 8.73 mmol), P(t-Bu).sub.3
(3.53 g, 17.5 mmol), NaOt-Bu (50.3 g, 523.8 mmol) and toluene (1800
ml) in the same manner as described in the synthesis method of the
compound Sub 2-1 above, whereby a compound Sub 2-7 was obtained in
an amount of 36.2 g in 77% yield.
5. Synthesis of Sub 2-9
##STR00161##
[0203] The compound Sub 2-9 was synthesized by using
2-bromo-9,9-diphenyl-9H-fluorene (93.9 g, 236.2 mmol), toluene
(2250 ml), aniline (20 g, 214.8 mmol), Pd.sub.2(dba).sub.3 (9.83 g,
10.7 mmol), P(t-Bu).sub.3 (4.34 g, 21.5 mmol) and NaOt-Bu (62 g,
644.3 mmol) in the same manner as described in the synthesis method
of the compound Sub 2-1 above, whereby a compound Sub 2-9 was
obtained in an amount of 63.3 g in 72% yield.
6. Synthesis of Sub 2-12
##STR00162##
[0205] The compound Sub 2-12 was synthesized by using
2-bromo-9,9-diphenyl-9H-fluorene (64.6 g, 162.5 mmol), toluene
(1550 ml), [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol),
Pd.sub.2(dba).sub.3 (6.76 g, 162.5 mmol), P(t-Bu).sub.3 (3 g, 14.8
mmol) and NaOt-Bu (42.6 g, 443.2 mmol) in the same manner as
described in the synthesis method of the compound Sub 2-1 above,
whereby a compound Sub 2-12 was obtained in an amount of 53.8 g in
75% yield.
7. Synthesis of Sub 2-13
##STR00163##
[0207] The compound Sub 2-13 was synthesized by using
3-bromodibenzo[b,d]thiophene (42.8 g, 162.5 mmol), toluene (1550
ml), [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol),
Pd.sub.2(dba).sub.3 (6.76 g, 162.5 mmol), P(t-Bu).sub.3 (3 g, 14.8
mmol) and NaOt-Bu (42.6 g, 443.2 mmol) in the same manner as
described in the synthesis method of the compound Sub 2-1 above,
whereby a compound Sub 2-13 was obtained in an amount of 37.9 g in
73% yield.
8. Synthesis of Sub 2-17
##STR00164##
[0209] The compound Sub 2-17 was synthesized by using
1-bromo-4-methoxybenzene (36 g, 192.1 mmol), naphthalen-1-amine (25
g, 174.6 mmol), Pd.sub.2(dba).sub.3 (8.0 g, 8.73 mmol),
P(t-Bu).sub.3 (3.53 g, 17.5 mmol), NaOt-Bu (50.3 g, 523.8 mmol) and
toluene (1800 ml) in the same manner as described in the synthesis
method of the compound Sub 2-1 above, whereby a compound Sub 2-17
was obtained in an amount of 32.2 g in 74% yield.
9. Synthesis of Sub 2-26
##STR00165##
[0211] The compound Sub 2-26 was synthesized by using
5'-bromo-1,1':3',1''-terphenyl (73.04 g, 236.2 mmol), amine (20 g,
214.8 mmol), Pd.sub.2(dba).sub.3 (9.83 g, 10.7 mmol), P(t-Bu).sub.3
(4.34 g, 21.5 mmol), NaOt-Bu (62 g, 644.3 mmol) and toluene (2250
ml) in the same manner as described in the synthesis method of the
compound Sub 2-1 above, whereby a compound Sub 2-26 was obtained in
an amount of 49 g in 71% yield.
10. Synthesis of Sub 2-31
##STR00166##
[0213] The compound Sub 2-31 was synthesized by
2-bromo-9-phenyl-9H-carbazole (52.4 g, 162.5 mmol), toluene (1550
mL), [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol),
Pd.sub.2(dba).sub.3 (6.76 g, 162.5 mmol), P(t-Bu).sub.3 (3 g, 14.8
mmol) and NaOt-Bu (42.6 g, 443.2 mmol) in the same manner as
described in the synthesis method of the compound Sub 2-1 above,
whereby a compound Sub 2-26 was obtained in an amount of 45.4 g in
68% yield.
[0214] Examples of Sub 2 compounds include, but are not limited to,
the following compounds, and FD-MS data of the compounds are given
in Table 2 below.
##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171##
##STR00172## ##STR00173## ##STR00174## ##STR00175##
##STR00176##
TABLE-US-00002 [ 2] Compound FD-MS compound FD-MS Sub 2-1 m/z =
169.09(C.sub.12H.sub.11N = 169.22) Sub 2-2 m/z =
245.12(C.sub.18H.sub.15N = 245.32) Sub 2-3 m/z =
245.12(C.sub.18H.sub.15N = 245.32) Sub 2-4 m/z =
321.15(C.sub.24H.sub.19N = 321.41) Sub 2-5 m/z = 321.15
(C.sub.24H.sub.19N = 321.41) Sub 2-6 m/z = 269.12(C.sub.20H.sub.15N
= 269.34) Sub 2-7 m/z = 269.12(C.sub.20H.sub.15N = 269.34) Sub 2-8
m/z = 295.14(C.sub.22H.sub.17N = 295.38) Sub 2-9 m/z =
409.18(C.sub.31H.sub.23N = 409.52) Sub 2-10 m/z =
483.20(C.sub.37H.sub.25N = 483.60) Sub 2-11 m/z =
459.20(C.sub.35H.sub.25N = 459.58) Sub 2-12 m/z =
485.21(C.sub.37H.sub.27N = 485.62) Sub 2-13 m/z =
351.11(C.sub.34H.sub.17NS = 351.46) Sub 2-14 m/z =
335.13(C.sub.24H.sub.17NO = 335.40) Sub 2-15 m/z =
297.13(C.sub.20H.sub.15N.sub.3 = 297.35) Sub 2-16 m/z =
219.10(C.sub.16H.sub.13N = 219.28) Sub 2-17 m/z =
249.12(C.sub.17H.sub.15NO = 249.31) Sub 2-18 m/z =
197.12(C.sub.14H.sub.15N = 197.28) Sub 2-19 m/z =
229.11(C.sub.14H.sub.15NO.sub.2 = 229.27) Sub 2-20 m/z =
174.12(C.sub.12H.sub.6D.sub.5N = 174.25) Sub 2-21 m/z =
281.21(C.sub.20H.sub.27N = 281.44) Sub 2-22 m/z =
321.15(C.sub.24H.sub.19N = 321.41) Sub 2-23 m/z =
321.15(C.sub.24H.sub.19N = 321.41) Sub 2-24 m/z =
321.15(C.sub.24H.sub.19N = 321.41) Sub 2-25 m/z =
321.15(C.sub.24H.sub.19N = 321.41) Sub 2-26 m/z =
321.15(C.sub.24H.sub.19N = 321.41) Sub 2-27 m/z =
297.13(C.sub.20H.sub.15N.sub.3 = 297.35) Sub 2-28 m/z =
275.08(C.sub.18H.sub.13NS = 275.37) Sub 2-29 m/z =
361.18(C.sub.27H.sub.23N = 361.48) Sub 2-30 m/z =
499.20(C.sub.36H.sub.25N.sub.3 = 499.60) Sub 2-31 m/z =
499.20(C.sub.36H.sub.22N.sub.2 = 410.51) Sub 2-32 m/z =
424.16(C.sub.30H.sub.20N.sub.2O = 424.49) Sub 2-33 m/z =
440.13(C.sub.30H.sub.20N.sub.2S = 440.56) Sub 2-34 m/z =
384.16(C.sub.28H.sub.20N.sub.2 = 384.47) Sub 2-35 m/z =
334.15(C.sub.24H.sub.18N.sub.2 = 334.41) Sub 2-36 m/z =
450.21(C.sub.33H.sub.26N.sub.2 = 450.57) Sub 2-37 m/z =
410.18(C.sub.30H.sub.22N.sub.2 = 410.51) Sub 2-38 m/z =
410.18(C.sub.30H.sub.22N.sub.2 = 410.51) Sub 2-39 m/z =
575.24(C.sub.42H.sub.29N.sub.3 = 575.70) Sub 2-40 m/z =
574.24(C.sub.43H.sub.30N.sub.2 = 574.71) Sub 2-41 m/z =
460.19(C.sub.34H.sub.24N.sub.2 = 460.57) Sub 2-42 m/z =
460.19(C.sub.34H.sub.24N.sub.2 = 460.57) Sub 2-43 m/z =
461.19(C.sub.33H.sub.23N.sub.3 = 461.56) Sub 2-44 m/z =
626.27(C.sub.47H.sub.34N.sub.2 = 626.79) Sub 2-45 m/z =
565.23(C.sub.39H.sub.27N.sub.5 = 565.67) Sub 2-46 m/z =
415.21(C.sub.30H.sub.17D.sub.5N.sub.2 = 415.54) Sub 2-47 m/z =
486.21(C.sub.36H.sub.26N.sub.2 = 486.61) Sub 2-48 m/z =
415.21(C.sub.30H.sub.17D.sub.5N.sub.2 = 415.54)
III. Synthesis Examples of Final Products
[0215] Sub 2 (1 eq) was dissolved in toluene in a round bottom
flask. Then, 1 (1.1 eq), Pd.sub.2(dba).sub.3 (0.05 eq),
P(t-Bu).sub.3 (0.1 eq) and NaOt-Bu (3 eq) were added into the round
bottom flask, and the mixture was stirred 100.degree. C. After the
completion of the reaction, the reaction product was extracted with
CH.sub.2Cl.sub.2 and water. The extracted organic layer was dried
over MgSO.sub.4 and concentrated. The concentrated resultant was
separated by silica gel column chromatography, and was then
recrystallized, whereby Final products was obtained.
1. Synthesis of Product P1-1
##STR00177##
[0217] Sub 2-1 (8 g, 47.3 mmol) was dissolved in in toluene (500
ml) in a round bottom flask. Then, Sub 1-1 (20.7 g, 52.0 mmol),
Pd.sub.2(dba).sub.3 (2.2 g, 2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73
mmol) and NaOt-Bu (13.6 g, 141.8 mmol) were added into the round
bottom flask, and the mixture was stirred at 100.degree. C. After
the completion of the reaction, the reaction product was extracted
with CH.sub.2Cl.sub.2 and water. The extracted organic layer was
dried over MgSO.sub.4 and concentrated. The concentrated resultant
was separated by silica gel column chromatography, and was then
recrystallized, whereby a compound P1-1 was obtained in an amount
of 16.2 g in 70% yield.
2. Synthesis of Product P1-4
##STR00178##
[0219] The compound P1-4 was synthesized by using Sub 2-4 (7.8 g,
24.9 mmol), Sub 1-1 (10.7 g, 27.4 mmol), Pd.sub.2(dba).sub.3 (1.14
g, 1.24 mmol), P(t-Bu).sub.3 (0.5 g, 2.49 mmol), NaOt-Bu (7.17 g,
74.7 mmol) and toluene (265 ml) in the same manner as described in
the synthesis method of the compound Product P1-1 above, whereby a
compound P1-4 was obtained in an amount of 10.6 g in 68% yield.
3. Synthesis of Product P1-8
##STR00179##
[0221] The compound P1-8 was synthesized by using Sub 2-9 (10 g,
24.4 mmol), Sub 2-9 (10 g, 24.4 mmol), Sub 1-1 (10.7 g, 27.4 mmol),
Pd.sub.2(dba).sub.3 (1.14 g, 1.24 mmol), P(t-Bu).sub.3 (0.5 g, 2.49
mmol), NaOt-Bu (7.17 g, 74.7 mmol) and toluene (265 ml) in the same
manner as described in the synthesis method of the compound Product
P1-1 above, whereby a compound P1-8 was obtained in an amount of
11.5 g in 77% yield.
4. Synthesis of Product P1-17
##STR00180##
[0223] The compound P1-17 was synthesized by using Sub 2-13 (10.0
g, 28.5 mmol), Sub 1-4 (14.0 g, 31.3 mmol), Pd.sub.2(dba).sub.3
(1.3 g, 1.42 mmol), P(t-Bu).sub.3 (0.6 g, 2.85 mmol), NaOt-Bu (8.2
g, 85.4 mmol) and toluene (300 ml) in the same manner as described
in the synthesis method of the compound Product P1-1 above, whereby
a compound P1-17 was obtained in an amount of 13.5 g in 66%
yield.
5. Synthesis of Product P1-49
##STR00181##
[0225] The compound P2-49 was synthesized by using Sub 2-6 (11.0 g,
37.13 mmol), Sub 1-65 (23.7 g, 40.84 mmol), Pd.sub.2(dba).sub.3
(1.7 g, 1.9 mmol), P(t-Bu).sub.3 (0.8 g, 3.7 mmol), NaOt-Bu (10.7
g, 111.4 mmol) and toluene (390 ml) in the same manner as described
in the synthesis method of the compound Product P1-1 above, whereby
a compound P2-49 was obtained in an amount of 24.7 g in 73%
yield.
6. Synthesis of Product P2-77
##STR00182##
[0227] The compound P2-77 was synthesized by using Sub 2-1 (8.0 g,
47.3 mmol), Sub 1-68 (28.6 g, 52 mmol), Pd.sub.2(dba).sub.3 (2.2 g,
2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8
mmol) and toluene (500 ml) in the same manner as described in the
synthesis method of the compound Product P1-1 above, whereby a
compound P2-77 was obtained in an amount of 22.7 g in 75%
yield.
7. Synthesis of Product P3-2
##STR00183##
[0229] The compound P3-4 was synthesized by Sub 2-28 (22.4 g, 47.3
mmol), Sub 1-103 (14.3 g, 52 mmol), Pd.sub.2(dba).sub.3 (2.2 g, 2.4
mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol)
and toluene (500 mL) in the same manner as described in the
synthesis method of the compound Product P1-1 above, whereby a
compound P3-2 was obtained in an amount of 23.1 g in 73% yield.
8. Synthesis of Product P3-22
##STR00184##
[0231] The compound P3-22 was synthesized by using Sub 2-29 (22.4
g, 47.3 mmol), Sub 1-121 (18.8 g, 52 mmol), Pd.sub.2(dba).sub.3
(2.2 g, 2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g,
141.8 mmol) and toluene (500 mL) in the same manner as described in
the synthesis method of the compound Product P1-1 above, whereby a
compound P3-22 was obtained in an amount of 24.3 g in 68%
yield.
9. Synthesis of Product P4-2
##STR00185##
[0233] The compound P4-2 was synthesized by using Sub 2-31 (19.4 g,
47.3 mmol), Sub 1-1 (20.7 g, 52 mmol), Pd.sub.2(dba).sub.3 (2.2 g,
2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8
mmol) and toluene (500 mL) in the same manner as described in the
synthesis method of the compound Product P1-1 above, whereby a
compound P4-2 was obtained in an amount of 30.3 g in 80% yield.
10. Synthesis of Product P4-9
##STR00186##
[0235] The compound P4-9 was synthesized by using Sub 2-36 (21.3,
47.3 mmol), Sub 1-1 (20.7 g, 52 mmol), Pd.sub.2(dba).sub.3 (2.2 g,
2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8
mmol) and toluene (500 mL) in the same manner as described in the
synthesis method of the compound Product P1-1 above, whereby a
compound P4-9 was obtained in an amount of 32.7 g in 82% yield.
11. Synthesis of Product P4-15
##STR00187##
[0237] The compound P4-15 was synthesized by using Sub 2-33 (20.8
g, 47.3 mmol), Sub 1-129 (24.7 g, 52 mmol), Pd.sub.2(dba).sub.3
(2.2 g, 2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g,
141.8 mmol) and toluene (500 mL) in the same manner as described in
the synthesis method of the compound Product P1-1 above, whereby a
compound P4-15 was obtained in an amount of 33.8 g in 78%
yield.
12. Synthesis of Product P4-20
##STR00188##
[0239] The compound P4-20 was synthesized by using Sub 2-35 (15.8
g, 47.3 mmol), Sub 1-130 (26.8 g, 52 mmol), Pd.sub.2(dba).sub.3
(2.2 g, 2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g,
141.8 mmol) and toluene (500 mL) in the same manner as described in
the synthesis method of the compound Product P1-1 above, whereby a
compound P4-20 was obtained in an amount of 32.3 g in 81%
yield.
13. Synthesis of Product P4-29
##STR00189##
[0241] The compound P4-29 was synthesized by using Sub 2-41 (21.8
g, 47.3 mmol), Sub 1-56 (20.7 g, 52 mmol), Pd.sub.2(dba).sub.3 (2.2
g, 2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g,
141.8 mmol) and toluene (500 mL) in the same manner as described in
the synthesis method of the compound Product P1-1 above, whereby a
compound P4-29 was obtained in an amount of 32.0 g in 79%
yield.
14. Synthesis of Product P4-33
##STR00190##
[0243] The compound P4-33 was synthesized by using Sub 2-45 (26.8
g, 47.3 mmol), Sub 1-56 (20.7 g, 52 mmol), Pd.sub.2(dba).sub.3 (2.2
g, 2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g,
141.8 mmol) and toluene (500 mL) in the same manner as described in
the synthesis method of the compound Product P1-1 above, whereby a
compound P4-33 was obtained in an amount of 36.7 g in 80%
yield.
15. Synthesis of Product P4-36
##STR00191##
[0245] The compound P4-36 was synthesized by using Sub 2-48 (19.7
g, 47.3 mmol), Sub 1-56 (20.7 g, 52 mmol), Pd.sub.2(dba).sub.3 (2.2
g, 2.4 mmol), P(t-Bu).sub.3 (1 g, 4.73 mmol), NaOt-Bu (13.6 g,
141.8 mmol) and toluene (500 mL) in the same manner as described in
the synthesis method of the compound Product P1-1 above, whereby a
compound P4-36 was obtained in an amount of 29.0 g in 76%
yield.
[0246] FD-MS data of the final products, P1-1 to P1-112, P2-1 to
P2-112, P3-1 to P3-38, and P4-1 to P4-36, synthesized according to
the above synthesis example are given in Table 3 below.
TABLE-US-00003 TABLE 3 Compound FD-MS compound FD-MS P1-1 m/z =
486.21(C.sub.36H.sub.26N.sub.2 = 486.61) P1-2 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P1-3 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P1-4 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P1-5 m/z =
586.24(C.sub.44H.sub.30N.sub.2 = 586.72) P1-6 m/z =
586.24(C.sub.44H.sub.30N.sub.2 = 586.72) P1-7 m/z =
612.26(C.sub.46H.sub.32N.sub.2 = 612.76) P1-8 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P1-9 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P1-10 m/z =
800.32(C.sub.61H.sub.40N.sub.2 = 800.98) P1-11 m/z =
536.23(C.sub.40H.sub.28N.sub.2 = 536.66) P1-12 m/z =
688.29(C.sub.52H.sub.36N.sub.2 = 688.86) P1-13 m/z =
852.35(C.sub.65H.sub.44N.sub.2 = 853.06) P1-14 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P1-15 m/z =
688.29(C.sub.52H.sub.36N.sub.2 = 688.86) P1-16 m/z =
662.27(C.sub.50H.sub.34N.sub.2 = 662.82) P1-17 m/z =
718.24(C.sub.52H.sub.34N.sub.2S = 718.90) P1-18 m/z =
702.27(C.sub.52H.sub.34N.sub.2O = 702.84) P1-19 m/z =
664.26(C.sub.48H.sub.32N.sub.4 = 664.79) P1-20 m/z =
664.26(C.sub.48H.sub.32N.sub.4 = 664.79) P1-21 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P1-22 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P1-23 m/z =
780.35(C.sub.56H.sub.48N.sub.2S = 781.06) P1-24 m/z =
665.26(C.sub.47H.sub.31N.sub.5 = 665.78) P1-25 m/z =
526.24(C.sub.39H.sub.30N.sub.2 = 526.67) P1-26 m/z =
739.30(C.sub.55H.sub.37N.sub.3 = 739.90) P1-27 m/z =
642.27(C.sub.47H.sub.34N.sub.2O = 642.79) P1-28 m/z =
790.31(C.sub.58H.sub.38N.sub.4 = 790.95) P1-29 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P1-30 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P1-31 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P1-32 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-33 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P1-34 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P1-35 m/z =
852.35(C.sub.65H.sub.44N.sub.2 = 853.06) P1-36 m/z =
1016.41(C.sub.78H.sub.52N.sub.2 = 1017.26) P1-37 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-38 m/z =
1040.41(C.sub.80H.sub.52N.sub.2 = 1041.28) P1-39 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P1-40 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-41 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-42 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-43 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-44 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-45 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P1-46 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P1-47 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P1-48 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-49 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-50 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-51 m/z =
852.35(C.sub.65H.sub.44N.sub.2 = 853.06) P1-52 m/z =
1016.41(C.sub.78H.sub.52N.sub.2 = 1017.26) P1-53 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-54 m/z =
1040.41(C.sub.80H.sub.52N.sub.2 = 1041.28) P1-55 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P1-56 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-57 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-58 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-59 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-60 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-61 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P1-62 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P1-63 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P1-64 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-65 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-66 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-67 m/z =
852.35(C.sub.65H.sub.44N.sub.2 = 853.06) P1-68 m/z =
1016.41(C.sub.78H.sub.52N.sub.2 = 1017.26) P1-69 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-70 m/z =
1040.41(C.sub.80H.sub.52N.sub.2 = 1041.28) P1-71 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P1-72 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-73 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-74 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-75 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-76 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P1-77 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P1-78 m/z =
714.30(C.sub.54H.sub.38N.sub.2 = 714.89) P1-79 m/z =
714.30(C.sub.54H.sub.38N.sub.2 = 714.89) P1-80 m/z =
790.33(C.sub.60H.sub.42N.sub.2 = 790.99) P1-81 m/z =
738.30(C.sub.56H.sub.38N.sub.2 = 738.91) P1-82 m/z =
738.30(C.sub.56H.sub.38N.sub.2 = 738.91) P1-83 m/z =
764.32(C.sub.58H.sub.40N.sub.2 = 764.95) P1-84 m/z =
928.38(C.sub.71H.sub.48N.sub.2 = 929.15) P1-85 m/z =
790.33(C.sub.60H.sub.42N.sub.2 = 790.99) P1-86 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P1-87 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80)) P1-88 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P1-89 m/z =
648.33(C.sub.48H.sub.24D.sub.10N.sub.2 = 648.86) P1-90 m/z =
724.37(C.sub.54H.sub.28D.sub.10N.sub.2 = 724.95) P1-91 m/z =
795.37(C.sub.60H.sub.37D.sub.5N.sub.2 = 796.02) P1-92 m/z =
643.30(C.sub.48H.sub.29D.sub.5N.sub.2 = 643.83) P1-93 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P1-94 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-95 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P1-96 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-97 m/z =
854.37(C.sub.65H.sub.46N.sub.2 = 855.07) P1-98 m/z =
836.34(C.sub.61H.sub.44N.sub.2O.sub.2 = 837.01) P1-99 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-100 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-101 m/z =
692.23(C.sub.50H.sub.32N.sub.2S = 692.87) P1-102 m/z =
692.23(C.sub.50H.sub.32N.sub.2S = 692.87) P1-103 m/z =
718.24(C.sub.52H.sub.34N.sub.2S = 718.90) P1-104 m/z =
882.31(C.sub.65H.sub.42N.sub.2S = 883.11) P1-105 m/z =
676.25(C.sub.50H.sub.32N.sub.2O = 676.80) P1-106 m/z =
676.25(C.sub.50H.sub.32N.sub.2O = 676.80) P1-107 m/z =
702.27(C.sub.52H.sub.34N.sub.2O = 702.84) P1-108 m/z =
866.33(C.sub.65H.sub.42N.sub.2O = 867.04) P1-109 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-110 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P1-111 m/z =
742.24(C.sub.54H.sub.34N.sub.2S = 742.93) P1-112 m/z =
726.27(C.sub.54H.sub.34N.sub.2O = 726.86) P2-1 m/z =
486.21(C.sub.36H.sub.26N.sub.2 = 486.61) P2-2 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P2-3 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P2-4 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P2-5 m/z =
586.24(C.sub.44H.sub.30N.sub.2 = 586.72) P2-6 m/z =
586.24(C.sub.44H.sub.30N.sub.2 = 586.72) P2-7 m/z =
612.26(C.sub.46H.sub.32N.sub.2 = 612.76) P2-8 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P2-9 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P2-10 m/z =
800.32(C.sub.61H.sub.40N.sub.2 = 800.98) P2-11 m/z =
536.23(C.sub.40H.sub.28N.sub.2 = 536.66) P2-12 m/z =
688.29(C.sub.52H.sub.36N.sub.2 = 688.86) P2-13 m/z =
852.35(C.sub.65H.sub.44N.sub.2 = 853.06) P2-14 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P2-15 m/z =
688.29(C.sub.52H.sub.36N.sub.2 = 688.86) P2-16 m/z =
662.27(C.sub.50H.sub.34N.sub.2 = 662.82) P2-17 m/z =
718.24(C.sub.52H.sub.34N.sub.2S = 718.90) P2-18 m/z =
702.27(C.sub.52H.sub.34N.sub.2O = 702.84) P2-19 m/z =
664.26(C.sub.48H.sub.32N.sub.4 = 664.79) P2-20 m/z =
664.26(C.sub.48H.sub.32N.sub.4 = 664.79) P2-21 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P2-22 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P2-23 m/z =
780.35(C.sub.56H.sub.48N.sub.2S = 781.06) P2-24 m/z =
665.26(C.sub.47H.sub.31N.sub.5 = 665.78) P2-25 m/z =
526.24(C.sub.39H.sub.30N.sub.2 = 526.67) P2-26 m/z =
739.30(C.sub.55H.sub.37N.sub.3 = 739.90) P2-27 m/z =
642.27(C.sub.47H.sub.34N.sub.2O = 642.79) P2-28 m/z =
790.31(C.sub.58H.sub.38N.sub.4 = 790.95) P2-29 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P2-30 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P2-31 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P2-32 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-33 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P2-34 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P2-35 m/z =
852.35(C.sub.65H.sub.44N.sub.2 = 853.06) P2-36 m/z =
1016.41(C.sub.78H.sub.52N.sub.2 = 1017.26) P2-37 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-38 m/z =
1040.41(C.sub.80H.sub.52N.sub.2 = 1041.28) P2-39 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P2-40 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-41 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-42 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-43 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-44 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-45 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P2-46 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P2-47 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P2-48 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-49 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-50 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-51 m/z =
852.35(C.sub.65H.sub.44N.sub.2 = 853.06) P2-52 m/z =
1016.41(C.sub.78H.sub.52N.sub.2 = 1017.26) P2-53 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-54 m/z =
1040.41(C.sub.80H.sub.52N.sub.2 = 1041.28) P2-55 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P2-56 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-57 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-58 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-59 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-60 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-61 m/z =
726.30(C.sub.55H.sub.38N.sub.2 = 726.90) P2-62 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P2-63 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P2-64 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-65 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-66 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-67 m/z =
852.35(C.sub.65H.sub.44N.sub.2 = 853.06) P2-68 m/z =
1016.41(C.sub.78H.sub.52N.sub.2 = 1017.26) P2-69 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-70 m/z =
1040.41(C.sub.80H.sub.52N.sub.2 = 1041.28) P2-71 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P2-72 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-73 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-74 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-75 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-76 m/z =
878.37(C.sub.67H.sub.46N.sub.2 = 879.10) P2-77 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P2-78 m/z =
714.30(C.sub.54H.sub.38N.sub.2 = 714.89) P2-79 m/z =
714.30(C.sub.54H.sub.38N.sub.2 = 714.89) P2-80 m/z =
790.33(C.sub.60H.sub.42N.sub.2 = 790.99) P2-81 m/z =
738.30(C.sub.56H.sub.38N.sub.2 = 738.91) P2-82 m/z =
738.30(C.sub.56H.sub.38N.sub.2 = 738.91) P2-83 m/z =
764.32(C.sub.58H.sub.40N.sub.2 = 764.95) P2-84 m/z =
928.38(C.sub.71H.sub.48N.sub.2 = 929.15) P2-85 m/z =
790.33(C.sub.60H.sub.42N.sub.2 = 790.99) P2-86 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P2-87 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80)) P2-88 m/z =
638.27(C.sub.48H.sub.34N.sub.2 = 638.80) P2-89 m/z =
648.33(C.sub.48H.sub.24D.sub.10N.sub.2 = 648.86) P2-90 m/z =
724.37(C.sub.54H.sub.28D.sub.10N.sub.2 = 724.95) P2-91 m/z =
795.37(C.sub.60H.sub.37D.sub.5N.sub.2 = 796.02) P2-92 m/z =
643.30(C.sub.48H.sub.29D.sub.5N.sub.2 = 643.83) P2-93 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P2-94 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-95 m/z =
776.32(C.sub.59H.sub.40N.sub.2 = 776.96) P2-96 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-97 m/z =
854.37(C.sub.65H.sub.46N.sub.2 = 855.07) P2-98 m/z =
836.34(C.sub.61H.sub.44N.sub.2O.sub.2 = 837.01) P2-99 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-100 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-101 m/z =
692.23(C.sub.50H.sub.32N.sub.2S = 692.87) P2-102 m/z =
692.23(C.sub.50H.sub.32N.sub.2S = 692.87) P2-103 m/z =
718.24(C.sub.52H.sub.34N.sub.2S = 718.90) P2-104 m/z =
882.31(C.sub.65H.sub.42N.sub.2S = 883.11) P2-105 m/z =
676.25(C.sub.50H.sub.32N.sub.2O = 676.80) P2-106 m/z =
676.25(C.sub.50H.sub.32N.sub.2O = 676.80) P2-107 m/z =
702.27(C.sub.52H.sub.34N.sub.2O = 702.84) P2-108 m/z =
866.33(C.sub.65H.sub.42N.sub.2O = 867.04) P2-109 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-110 m/z =
826.33(C.sub.63H.sub.42N.sub.2 = 827.02) P2-111 m/z =
742.24(C.sub.54H.sub.34N.sub.2S = 742.93) P2-112 m/z =
726.27(C.sub.54H.sub.34N.sub.2O = 726.86) P3-1 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P3-2 m/z =
668.23(C.sub.48H.sub.32N.sub.2S = 668.85) P3-3 m/z =
728.28(C.sub.54H.sub.36N.sub.2O = 728.88) P3-4 m/z =
754.33(C.sub.57H.sub.42N.sub.2 = 754.96) P3-5 m/z =
802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P3-6 m/z =
800.32(C.sub.16H.sub.40N.sub.2 = 800.98) P3-7 m/z =
612.26(C.sub.46H.sub.32N.sub.2 = 612.76) P3-8 m/z =
718.24(C.sub.52H.sub.34N.sub.2S = 718.90) P3-9 m/z =
804.31(C.sub.60H.sub.40N.sub.2O = 804.97) P3-10 m/z =
754.33(C.sub.57H.sub.42N.sub.2 = 754.96) P3-11 m/z =
928.38(C.sub.17H.sub.48N.sub.2 = 929.15) P3-12 m/z =
926.37(C.sub.71H.sub.46N.sub.2 = 927.14) P3-13 m/z =
688.29(C.sub.52H.sub.36N.sub.2 = 688.86) P3-14 m/z =
794.28(C.sub.58H.sub.38N.sub.2S = 795.00) P3-15 m/z =
729.28(C.sub.53H.sub.35N.sub.3O = 729.86) P3-16 m/z =
805.35(C.sub.60H.sub.43N.sub.3 = 806.00) P3-17 m/z =
854.34(C.sub.63H.sub.42N.sub.4 = 855.03) P3-18 m/z =
802.31(C.sub.59H.sub.38N.sub.4 = 802.96) P3-19 m/z =
562.24(C.sub.42H.sub.30N.sub.2 = 562.70) P3-20 m/z =
668.23(C.sub.48H.sub.32N.sub.2S = 668.85) P3-21 m/z =
728.28(C.sub.54H.sub.36N.sub.2O = 728.88) P3-22 m/z =
754.33(C.sub.57H.sub.42N.sub.2 = 754.96)
P3-23 m/z = 802.33(C.sub.61H.sub.42N.sub.2 = 803.00) P3-24 m/z =
800.32(C.sub.61H.sub.40N.sub.2 = 800.98) P3-25 m/z =
612.26(C.sub.46H.sub.32N.sub.2 = 612.76) P3-26 m/z =
718.24(C.sub.52H.sub.34N.sub.2S = 718.90) P3-27 m/z =
804.31(C.sub.60H.sub.40N.sub.2O = 804.97) P3-28 m/z =
754.33(C.sub.57H.sub.42N.sub.2 = 754.96) P3-29 m/z =
928.38(C.sub.71H.sub.48N.sub.2 = 929.15) P3-30 m/z =
926.37(C.sub.71H.sub.46N.sub.2 = 927.14) P3-31 m/z =
688.29(C.sub.52H.sub.36N.sub.2 = 688.86) P3-32 m/z =
794.28(C.sub.58H.sub.38N.sub.2S = 795.00) P3-33 m/z =
729.28(C.sub.53H.sub.35N.sub.3O = 729.86) P3-34 m/z =
805.35(C.sub.60H.sub.43N.sub.3 = 806.00) P3-35 m/z =
854.34(C.sub.63H.sub.42N.sub.4 = 855.03) P3-36 m/z =
802.31(C.sub.59H.sub.38N.sub.4 = 802.96) P3-37 m/z =
714.30(C.sub.54H.sub.38N.sub.2 = 714.89) P3-38 m/z =
714.30(C.sub.54H.sub.38N.sub.2 = 714.89) P4-1 m/z =
816.33(C.sub.60H.sub.40N.sub.4 = 816.99) P4-2 m/z =
727.30(C.sub.54H.sub.37N.sub.3 = 727.89) P4-3 m/z =
741.28(C.sub.54H.sub.35N.sub.3O = 741.88) P4-4 m/z =
757.26(C.sub.54H.sub.35N.sub.3S = 757.94) P4-5 m/z =
701.28(C.sub.52H.sub.35N.sub.3 = 701.85) P4-6 m/z =
803.33(C.sub.60H.sub.41N.sub.3 = 803.99) P4-7 m/z =
757.26(C.sub.54H.sub.35N.sub.3S = 757.94) P4-8 m/z =
909.32(C.sub.66H.sub.43N.sub.3S = 910.13) P4-9 m/z =
767.33(C.sub.57H.sub.41N.sub.3 = 767.96) P4-10 m/z =
833.29(C.sub.60H.sub.39N.sub.3S = 834.04) P4-11 m/z =
701.28(C.sub.52H.sub.35N.sub.3 = 701.85) P4-12 m/z =
807.27(C.sub.58H.sub.37N.sub.3S = 808.00) P4-13 m/z =
803.33(C.sub.60H.sub.41N.sub.3 = 803.99) P4-14 m/z =
727.30(C.sub.54H.sub.37N.sub.3 = 727.89) P4-15 m/z =
833.29(C.sub.60H.sub.39N.sub.3S = 834.04) P4-16 m/z =
777.31(C.sub.58H.sub.39N.sub.3 = 777.95) P4-17 m/z =
727.30(C.sub.54H.sub.37N.sub.3 = 727.89) P4-18 m/z =
777.31(C.sub.58H.sub.39N.sub.3 = 777.95) P4-19 m/z =
757.26(C.sub.54H.sub.35N.sub.3S = 757.94) P4-20 m/z =
767.33(C.sub.57H.sub.41N.sub.3 = 767.96) P4-21 m/z =
817.35(C.sub.61H.sub.43N.sub.3 = 818.01) P4-22 m/z =
727.30(C.sub.54H.sub.37N.sub.3 = 727.89) P4-23 m/z =
892.36(C.sub.66H.sub.44N.sub.4 = 893.08) P4-24 m/z =
891.36(C.sub.67H.sub.45N.sub.3 = 892.09) P4-25 m/z =
777.31(C.sub.58H.sub.39N.sub.3 = 777.95) P4-26 m/z =
817.35(C.sub.61H.sub.43N.sub.3 = 818.01) P4-27 m/z =
803.33(C.sub.60H.sub.41N.sub.3 = 803.99) P4-28 m/z =
777.31(C.sub.58H.sub.39N.sub.3 = 777.95) P4-29 m/z =
777.31(C.sub.58H.sub.39N.sub.3 = 777.95) P4-30 m/z =
777.31(C.sub.58H.sub.39N.sub.3 = 777.95) P4-31 m/z =
778.31(C.sub.57H.sub.38N.sub.4 = 778.94) P4-32 m/z =
943.39(C.sub.71H.sub.49N.sub.3 = 944.17) P4-33 m/z =
882.35(C.sub.63H.sub.42N.sub.6 = 883.05) P4-34 m/z =
732.33(C.sub.54H.sub.32D.sub.5N.sub.3 = 732.92) P4-35 m/z =
833.29(C.sub.60H.sub.39N.sub.3S = 834.04) P4-36 m/z =
732.33(C.sub.54H.sub.32D.sub.5N.sub.3 = 732.92)
Fabrication and Evaluation of Organic Electronic Element
[Example 1] Green OLEDs (A Hole Transport Layer)
[0247] Organic light emitting diodes (OLEDs) were fabricated
according to a conventional method by using a compound of the
present invention as a hole transport layer material.
[0248] First, an ITO layer (anode) was formed on a glass substrate,
and a film of 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine
("2-TNATA") was vacuum-deposited on the ITO layer to form a hole
injection layer with a thickness of 60 nm. Subsequently, P1-1 of
the present invention was vacuum-deposited with a thickness of 60
nm on the hole injection layer to form a hole transport layer.
[0249] Subsequently, a light emitting layer with a thickness of 30
nm was deposited on the hole transport layer by doping the hole
transport layer with 4,4'-N,N'-dicarbazole-biphenyl ("CBP") as a
host material and tris(2-phenylpyridine)-iridium ("Ir(ppy).sub.3)")
as a dopant material in a weight ratio of 90:10.
[0250] Next, a film of
((1,1'-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato) aluminum
("BAlq") was vacuum-deposited with a thickness of 10 nm on the
light emitting layer to form a hole blocking layer, and a film of
tris(8-quinolinolato)aluminum ("Alq.sub.3") was formed with a
thickness of 40 nm to form an electron transport layer.
[0251] Next, LiF as halogenated alkali metal was deposited with a
thickness of 0.2 nm on the electron transport layer to form an
electron injection layer, and then Al was deposited with a
thickness of 150 nm on the electron injection layer to form a
cathode. In this way, the OLED was completed.
[Example 2] to [Example 256] Green OLEDs (A Hole Transport
Layer)
[0252] The OLEDs were manufactured in the same manner as described
in Example 1, except that any one of the compounds P1-2 to P1-112,
P2-1 to P2-112, P3-1 to P3-6, P3-19 to P3-24, P3-37 and P3-38 of
the present invention in the Table 4 below was used as the hole
transport layer material, instead of the inventive compound
P1-1.
Comparative Example 1
[0253] An OLED was manufactured in the same manner as described in
Example 1, except that the following Comparative Compound 1 was
used as the hole transport layer material, instead of the inventive
compound P1-1.
##STR00192##
Comparative Example 2
[0254] An OLED was manufactured in the same manner as described in
Example 1, except that the following Comparative Compound 2 was
used as the hole transport layer material, instead of the inventive
compound P1-1.
##STR00193##
Comparative Example 3
[0255] An OLED was manufactured in the same manner as described in
Example 1, except that the following Comparative Compound 3 was
used as the hole transport layer material, instead of the inventive
compound P1-1.
##STR00194##
Comparative Example 4
[0256] An OLED was manufactured in the same manner as described in
Example 1, except that the following Comparative Compound 4 was
used as the hole transport layer material, instead of the inventive
compound P1-1.
##STR00195##
[0257] A forward bias DC voltage was applied to each of the OLEDs
manufactured through the Examples 1 to 238 and the Comparative
Examples 1 to 4, and electro-luminescence (EL) characteristics of
the OLED were measured by PR-650 (Photoresearch). Also, T90 life
span was measured by life span measuring equipment (Mcscience) at
the reference brightness of 5000 cd/m.sup.2. Evaluation results are
in the Table 4 below.
TABLE-US-00004 TABLE 4 Current Voltage Density Brightness
Efficiency Lifetime CIE Compound (V) (mA/cm.sup.2) (cd/m.sup.2)
(cd/A) T(95) x y Com. Ex (1) Com. Com (1) 5.6 17.9 5000.0 27.9 68.2
0.33 0.62 Com. Ex (2) Com. Com (2) 5.1 15.2 5000.0 33.0 115.9 0.33
0.61 Com. Ex (3) Com. Com (3) 5.3 13.0 5000.0 38.6 101.4 0.33 0.61
Com. Ex (4) Com. Com (4) 5.5 14.2 5000.0 35.1 100.9 0.33 0.61 Ex.
(1) P1-1 5.3 10.2 5000.0 49.1 125.1 0.33 0.62 Ex. (2) P1-2 5.4 10.0
5000.0 49.8 138.4 0.33 0.61 Ex. (3) P1-3 5.5 10.8 5000.0 46.4 121.2
0.33 0.61 Ex. (4) P1-4 5.4 11.0 5000.0 45.4 149.6 0.33 0.61 Ex. (5)
P1-5 5.4 10.2 5000.0 49.2 143.2 0.33 0.62 Ex. (6) P1-6 5.3 10.4
5000.0 48.3 134.7 0.33 0.62 Ex. (7) P1-7 5.3 10.5 5000.0 47.6 114.8
0.33 0.61 Ex. (8) P1-8 5.5 10.9 5000.0 45.9 140.2 0.33 0.62 Ex. (9)
P1-9 5.3 10.2 5000.0 49.0 104.7 0.33 0.61 Ex. (10) P1-10 5.5 10.4
5000.0 48.1 107.3 0.33 0.62 Ex. (11) P1-11 5.4 10.1 5000.0 49.4
140.6 0.33 0.61 Ex. (12) P1-12 5.3 10.0 5000.0 49.9 136.9 0.33 0.61
Ex. (13) P1-13 5.4 10.5 5000.0 47.5 125.9 0.33 0.61 Ex. (14) P1-14
5.4 10.3 5000.0 48.5 129.6 0.33 0.62 Ex. (15) P1-15 5.4 10.3 5000.0
48.7 117.2 0.33 0.61 Ex. (16) P1-16 5.4 11.0 5000.0 45.5 134.9 0.33
0.61 Ex. (17) P1-17 5.5 10.8 5000.0 46.3 124.6 0.33 0.62 Ex. (18)
P1-18 5.4 10.2 5000.0 48.9 117.8 0.33 0.61 Ex. (19) P1-19 5.5 11.0
5000.0 45.4 116.0 0.33 0.62 Ex. (20) P1-20 5.3 10.9 5000.0 45.9
118.4 0.33 0.62 Ex. (21) P1-21 5.5 10.7 5000.0 46.6 103.5 0.33 0.61
Ex. (22) P1-22 5.4 10.3 5000.0 48.7 126.5 0.33 0.62 Ex. (23) P1-23
5.5 11.0 5000.0 45.5 131.3 0.33 0.62 Ex. (24) P1-24 5.5 10.3 5000.0
48.4 139.0 0.33 0.62 Ex. (25) P1-25 5.5 10.8 5000.0 46.3 142.0 0.33
0.62 Ex. (26) P1-26 5.4 10.4 5000.0 48.2 112.5 0.33 0.61 Ex. (27)
P1-27 5.4 10.1 5000.0 49.4 125.0 0.33 0.61 Ex. (28) P1-28 5.3 10.7
5000.0 46.7 109.0 0.33 0.61 Ex. (29) P1-29 5.5 10.9 5000.0 45.8
116.8 0.33 0.62 Ex. (30) P1-30 5.3 10.6 5000.0 47.1 108.8 0.33 0.62
Ex. (31) P1-31 5.5 11.0 5000.0 45.4 122.0 0.33 0.62 Ex. (32) P1-32
5.3 11.1 5000.0 45.1 104.5 0.33 0.61 Ex. (33) P1-33 5.4 10.1 5000.0
49.4 113.6 0.33 0.61 Ex. (34) P1-34 5.4 10.9 5000.0 45.8 104.9 0.33
0.62 Ex. (35) P1-35 5.4 10.7 5000.0 46.8 112.4 0.33 0.62 Ex. (36)
P1-36 5.4 10.3 5000.0 48.6 140.7 0.33 0.61 Ex. (37) P1-37 5.3 10.1
5000.0 49.3 148.9 0.33 0.62 Ex. (38) P1-38 5.5 10.5 5000.0 47.6
141.1 0.33 0.61 Ex. (39) P1-39 5.5 10.1 5000.0 49.4 119.2 0.33 0.62
Ex. (40) P1-40 5.4 10.2 5000.0 49.1 140.0 0.33 0.61 Ex. (41) P1-41
5.4 10.6 5000.0 47.2 127.7 0.33 0.62 Ex. (42) P1-42 5.4 10.6 5000.0
47.3 126.2 0.33 0.61 Ex. (43) P1-43 5.3 11.1 5000.0 45.2 129.9 0.33
0.62 Ex. (44) P1-44 5.4 10.7 5000.0 46.6 146.3 0.33 0.62 Ex. (45)
P1-45 5.3 11.0 5000.0 45.6 116.5 0.33 0.62 Ex. (46) P1-46 5.4 10.2
5000.0 49.1 133.9 0.33 0.61 Ex. (47) P1-47 5.5 10.8 5000.0 46.2
124.9 0.33 0.62 Ex. (48) P1-48 5.5 10.2 5000.0 48.8 144.4 0.33 0.61
Ex. (49) P1-49 5.4 10.3 5000.0 48.3 148.9 0.33 0.61 Ex. (50) P1-50
5.5 10.3 5000.0 48.4 139.4 0.33 0.61 Ex. (51) P1-51 5.4 10.3 5000.0
48.4 112.3 0.33 0.61 Ex. (52) P1-52 5.3 10.5 5000.0 47.6 116.9 0.33
0.62 Ex. (53) P1-53 5.5 10.2 5000.0 49.1 132.5 0.33 0.61 Ex. (54)
P1-54 5.4 11.0 5000.0 45.6 115.2 0.33 0.62 Ex. (55) P1-55 5.5 10.5
5000.0 47.8 130.9 0.33 0.61 Ex. (56) P1-56 5.5 10.6 5000.0 47.0
101.8 0.33 0.61 Ex. (57) P1-57 5.3 10.3 5000.0 48.4 129.2 0.33 0.62
Ex. (58) P1-58 5.3 11.0 5000.0 45.6 138.7 0.33 0.61 Ex. (59) P1-59
5.5 10.5 5000.0 47.4 103.0 0.33 0.61 Ex. (60) P1-60 5.5 10.6 5000.0
47.2 144.0 0.33 0.61 Ex. (61) P1-61 5.3 10.8 5000.0 46.5 144.6 0.33
0.62 Ex. (62) P1-62 5.4 10.7 5000.0 46.9 136.5 0.33 0.61 Ex. (63)
P1-63 5.3 10.9 5000.0 45.8 136.9 0.33 0.62 Ex. (64) P1-64 5.4 10.9
5000.0 45.9 148.7 0.33 0.62 Ex. (65) P1-65 5.5 10.5 5000.0 47.6
102.2 0.33 0.61 Ex. (66) P1-66 5.4 10.0 5000.0 49.8 116.5 0.33 0.62
Ex. (67) P1-67 5.4 10.6 5000.0 47.1 108.9 0.33 0.61 Ex. (68) P1-68
5.4 10.4 5000.0 47.9 129.8 0.33 0.62 Ex. (69) P1-69 5.4 11.1 5000.0
45.1 138.5 0.33 0.62 Ex. (70) P1-70 5.4 10.6 5000.0 47.0 144.4 0.33
0.62 Ex. (71) P1-71 5.3 10.4 5000.0 48.2 137.4 0.33 0.61 Ex. (72)
P1-72 5.3 10.9 5000.0 45.7 127.3 0.33 0.62 Ex. (73) P1-73 5.3 10.3
5000.0 48.7 112.1 0.33 0.61 Ex. (74) P1-74 5.3 11.1 5000.0 45.0
140.8 0.33 0.61 Ex. (75) P1-75 5.3 10.1 5000.0 49.5 119.1 0.33 0.61
Ex. (76) P1-76 5.3 10.2 5000.0 49.2 127.2 0.33 0.62 Ex. (77) P1-77
5.5 10.1 5000.0 49.4 115.6 0.33 0.62 Ex. (78) P1-78 5.4 10.2 5000.0
48.8 121.9 0.33 0.61 Ex. (79) P1-79 5.4 10.3 5000.0 48.5 128.4 0.33
0.62 Ex. (80) P1-80 5.3 10.8 5000.0 46.3 142.9 0.33 0.61 Ex. (81)
P1-81 5.4 10.1 5000.0 49.7 126.1 0.33 0.61 Ex. (82) P1-82 5.4 10.7
5000.0 46.5 130.2 0.33 0.62 Ex. (83) P1-83 5.5 10.2 5000.0 48.9
128.7 0.33 0.61 Ex. (84) P1-84 5.4 10.3 5000.0 48.7 114.1 0.33 0.61
Ex. (85) P1-85 5.4 10.5 5000.0 47.8 119.6 0.33 0.61 Ex. (86) P1-86
5.3 10.9 5000.0 45.8 142.8 0.33 0.62 Ex. (87) P1-87 5.4 10.6 5000.0
47.0 114.0 0.33 0.61 Ex. (88) P1-88 5.5 10.6 5000.0 47.3 120.6 0.33
0.62 Ex. (89) P1-89 5.5 11.0 5000.0 45.4 121.9 0.33 0.62 Ex. (90)
P1-90 5.4 10.9 5000.0 45.8 108.0 0.33 0.61 Ex. (91) P1-91 5.3 10.8
5000.0 46.1 139.9 0.33 0.62 Ex. (92) P1-92 5.4 10.3 5000.0 48.7
111.4 0.33 0.61 Ex. (93) P1-93 5.5 10.0 5000.0 50.0 122.0 0.33 0.62
Ex. (94) P1-94 5.3 10.7 5000.0 46.8 109.5 0.33 0.61 Ex. (95) P1-95
5.5 10.3 5000.0 48.6 144.9 0.33 0.61 Ex. (96) P1-96 5.4 11.1 5000.0
45.1 137.9 0.33 0.62 Ex. (97) P1-97 5.4 10.1 5000.0 49.6 143.9 0.33
0.61 Ex. (98) P1-98 5.5 10.6 5000.0 47.1 130.9 0.33 0.62 Ex. (99)
P1-99 5.3 10.7 5000.0 46.5 147.2 0.33 0.62 Ex. (100) P1-100 5.3
10.8 5000.0 46.3 108.6 0.33 0.61 Ex. (101) P1-101 5.3 10.1 5000.0
49.3 124.4 0.33 0.61 Ex. (102) P1-102 5.3 10.3 5000.0 48.5 132.0
0.33 0.61 Ex. (103) P1-103 5.3 11.0 5000.0 45.6 142.0 0.33 0.62 Ex.
(104) P1-104 5.4 10.6 5000.0 47.3 131.6 0.33 0.62 Ex. (105) P1-105
5.3 10.9 5000.0 46.0 126.8 0.33 0.62 Ex. (106) P1-106 5.4 10.5
5000.0 47.7 131.9 0.33 0.61 Ex. (107) P1-107 5.4 10.2 5000.0 49.0
138.4 0.33 0.61 Ex. (108) P1-108 5.5 10.6 5000.0 47.2 130.5 0.33
0.62 Ex. (109) P1-109 5.4 11.0 5000.0 45.4 104.3 0.33 0.62 Ex.
(110) P1-110 5.5 10.4 5000.0 48.3 105.0 0.33 0.62 Ex. (111) P1-111
5.5 10.2 5000.0 48.9 127.1 0.33 0.61 Ex. (112) P1-112 5.4 10.5
5000.0 47.8 121.9 0.33 0.61 Ex. (113) P2-1 5.4 12.0 5000.0 41.7
128.7 0.33 0.61 Ex. (114) P2-2 5.4 11.2 5000.0 44.6 139.5 0.33 0.61
Ex. (115) P2-3 5.3 12.3 5000.0 40.6 137.4 0.33 0.61 Ex. (116) P2-4
5.4 11.6 5000.0 43.2 143.3 0.33 0.62 Ex. (117) P2-5 5.4 11.8 5000.0
42.3 126.1 0.33 0.61 Ex. (118) P2-6 5.4 11.4 5000.0 44.0 117.9 0.33
0.62 Ex. (119) P2-7 5.4 11.3 5000.0 44.1 137.9 0.33 0.61 Ex. (120)
P2-8 5.5 11.1 5000.0 45.0 113.7 0.33 0.62 Ex. (121) P2-9 5.4 11.7
5000.0 42.6 136.6 0.33 0.61 Ex. (122) P2-10 5.4 11.3 5000.0 44.4
111.7 0.33 0.62 Ex. (123) P2-11 5.3 11.8 5000.0 42.3 147.2 0.33
0.61 Ex. (124) P2-12 5.4 11.3 5000.0 44.2 100.4 0.33 0.61 Ex. (125)
P2-13 5.4 12.3 5000.0 40.6 128.7 0.33 0.61 Ex. (126) P2-14 5.5 11.6
5000.0 43.0 125.4 0.33 0.62 Ex. (127) P2-15 5.4 11.6 5000.0 43.2
132.3 0.33 0.61 Ex. (128) P2-16 5.5 11.6 5000.0 43.0 120.3 0.33
0.62 Ex. (129) P2-17 5.3 12.2 5000.0 41.1 141.2 0.33 0.62 Ex. (130)
P2-18 5.4 12.3 5000.0 40.6 129.3 0.33 0.62 Ex. (131) P2-19 5.4 12.2
5000.0 41.0 126.2 0.33 0.61 Ex. (132) P2-20 5.3 11.7 5000.0 42.6
132.3 0.33 0.62 Ex. (133) P2-21 5.4 12.0 5000.0 41.8 127.9 0.33
0.62 Ex. (134) P2-22 5.5 11.3 5000.0 44.2 141.8 0.33 0.61 Ex. (135)
P2-23 5.4 11.6 5000.0 43.0 116.7 0.33 0.62 Ex. (136) P2-24 5.4 12.5
5000.0 40.1 113.0 0.33 0.61 Ex. (137) P2-25 5.3 12.3 5000.0 40.5
107.7 0.33 0.61 Ex. (138) P2-26 5.5 12.4 5000.0 40.4 107.7 0.33
0.61 Ex. (139) P2-27 5.3 12.5 5000.0 40.1 147.2 0.33 0.61 Ex. (140)
P2-28 5.4 11.4 5000.0 43.7 143.1 0.33 0.61 Ex. (141) P2-29 5.4 11.5
5000.0 43.6 104.9 0.33 0.62 Ex. (142) P2-30 5.4 11.9 5000.0 41.9
129.5 0.33 0.62 Ex. (143) P2-31 5.5 12.2 5000.0 41.1 129.9 0.33
0.62 Ex. (144) P2-32 5.5 12.3 5000.0 40.8 137.8 0.33 0.61 Ex. (145)
P2-33 5.4 11.2 5000.0 44.6 126.9 0.33 0.61 Ex. (146) P2-34 5.4 12.5
5000.0 40.1 108.1 0.33 0.62 Ex. (147) P2-35 5.4 11.9 5000.0 42.1
135.4 0.33 0.62 Ex. (148) P2-36 5.3 12.2 5000.0 40.9 106.3 0.33
0.62 Ex. (149) P2-37 5.5 11.9 5000.0 42.1 102.7 0.33 0.62 Ex. (150)
P2-38 5.3 11.3 5000.0 44.3 137.2 0.33 0.62 Ex. (151) P2-39 5.4 12.2
5000.0 41.0 132.0 0.33 0.61 Ex. (152) P2-40 5.4 11.7 5000.0 42.6
135.3 0.33 0.61 Ex. (153) P2-41 5.4 11.7 5000.0 42.9 130.5 0.33
0.62 Ex. (154) P2-42 5.5 11.4 5000.0 43.9 126.1 0.33 0.62 Ex. (155)
P2-43 5.3 11.9 5000.0 42.0 111.7 0.33 0.62 Ex. (156) P2-44 5.4 11.5
5000.0 43.4 121.9 0.33 0.61 Ex. (157) P2-45 5.4 11.7 5000.0 42.9
142.8 0.33 0.61 Ex. (158) P2-46 5.4 12.4 5000.0 40.2 121.0 0.33
0.61 Ex. (159) P2-47 5.5 12.1 5000.0 41.4 134.9 0.33 0.61 Ex. (160)
P2-48 5.5 12.0 5000.0 41.8 107.9 0.33 0.62 Ex. (161) P2-49 5.4 11.5
5000.0 43.3 109.4 0.33 0.62 Ex. (162) P2-50 5.4 11.4 5000.0 43.8
116.0 0.33 0.62 Ex. (163) P2-51 5.4 12.4 5000.0 40.2 128.9 0.33
0.62 Ex. (164) P2-52 5.4 11.8 5000.0 42.4 139.9 0.33 0.62 Ex. (165)
P2-53 5.5 11.2 5000.0 44.5 148.4 0.33 0.62 Ex. (166) P2-54 5.5 12.4
5000.0 40.4 108.1 0.33 0.62 Ex. (167) P2-55 5.5 11.2 5000.0 44.6
145.4 0.33 0.62 Ex. (168) P2-56 5.4 11.4 5000.0 44.0 108.7 0.33
0.61 Ex. (169) P2-57 5.4 12.1 5000.0 41.2 135.0 0.33 0.61 Ex. (170)
P2-58 5.5 12.3 5000.0 40.6 110.6 0.33 0.62 Ex. (171) P2-59 5.4 11.4
5000.0 43.9 147.2 0.33 0.61 Ex. (172) P2-60 5.4 12.5 5000.0 40.1
113.1 0.33 0.62 Ex. (173) P2-61 5.4 11.3 5000.0 44.2 143.9 0.33
0.62 Ex. (174) P2-62 5.4 11.7 5000.0 42.6 138.2 0.33 0.61 Ex. (175)
P2-63 5.5 11.4 5000.0 43.9 138.4 0.33 0.62 Ex. (176) P2-64 5.5 11.7
5000.0 42.8 102.3 0.33 0.61 Ex. (177) P2-65 5.4 12.3 5000.0 40.7
143.3 0.33 0.61 Ex. (178) P2-66 5.4 11.5 5000.0 43.5 105.8 0.33
0.62 Ex. (179) P2-67 5.4 11.7 5000.0 42.7 142.8 0.33 0.62 Ex. (180)
P2-68 5.4 11.4 5000.0 43.9 141.9 0.33 0.61 Ex. (181) P2-69 5.4 11.2
5000.0 44.7 146.5 0.33 0.62 Ex. (182) P2-70 5.5 11.3 5000.0 44.2
147.3 0.33 0.62 Ex. (183) P2-71 5.4 11.6 5000.0 43.1 142.0 0.33
0.61 Ex. (184) P2-72 5.4 11.6 5000.0 43.2 136.0 0.33 0.62 Ex. (185)
P2-73 5.4 12.1 5000.0 41.2 137.8 0.33 0.61 Ex. (186) P2-74 5.4 11.5
5000.0 43.3 111.1 0.33 0.62 Ex. (187) P2-75 5.3 11.8 5000.0 42.4
129.3 0.33 0.62 Ex. (188) P2-76 5.4 11.4 5000.0 43.9 100.8 0.33
0.61 Ex. (189) P2-77 5.4 11.4 5000.0 43.8 131.5 0.33 0.61 Ex. (190)
P2-78 5.3 11.2 5000.0 44.8 114.3 0.33 0.62 Ex. (191) P2-79 5.4 11.4
5000.0 44.0 116.1 0.33 0.61 Ex. (192) P2-80 5.5 11.6 5000.0 43.2
116.1 0.33 0.61 Ex. (193) P2-81 5.4 11.2 5000.0 44.7 123.3 0.33
0.62 Ex. (194) P2-82 5.4 11.4 5000.0 43.8 148.3 0.33 0.61 Ex. (195)
P2-83 5.5 11.3 5000.0 44.1 135.3 0.33 0.61 Ex. (196) P2-84 5.5 12.2
5000.0 40.9 128.0 0.33 0.61 Ex. (197) P2-85 5.5 11.6 5000.0 43.0
139.1 0.33 0.61 Ex. (198) P2-86 5.4 11.7 5000.0 42.7 125.3 0.33
0.62 Ex. (199) P2-87 5.3 11.1 5000.0 45.0 140.8 0.33 0.62 Ex. (200)
P2-88 5.5 11.6 5000.0 43.0 101.5 0.33 0.61 Ex. (201) P2-89 5.4 11.1
5000.0 45.0 133.6 0.33 0.61 Ex. (202) P2-90 5.5 11.2 5000.0 44.6
141.8 0.33 0.62 Ex. (203) P2-91 5.3 11.9 5000.0 42.0 149.2 0.33
0.62 Ex. (204) P2-92 5.3 11.5 5000.0 43.4 120.3 0.33 0.62 Ex. (205)
P2-93 5.4 11.6 5000.0 43.2 121.9 0.33 0.62 Ex. (206) P2-94 5.5 11.3
5000.0 44.4 145.6 0.33 0.61 Ex. (207) P2-95 5.5 11.8 5000.0 42.2
122.0 0.33 0.61 Ex. (208) P2-96 5.4 11.5 5000.0 43.5 134.2 0.33
0.61 Ex. (209) P2-97 5.3 11.7 5000.0 42.9 114.2 0.33 0.62 Ex. (210)
P2-98 5.4 11.7 5000.0 42.7 142.4 0.33 0.62 Ex. (211) P2-99 5.5 12.2
5000.0 40.9 112.8 0.33 0.62 Ex. (212) P2-100 5.4 11.7 5000.0 42.6
142.0 0.33 0.61 Ex. (213) P2-101 5.3 11.6 5000.0 43.1 127.1 0.33
0.61 Ex. (214) P2-102 5.5 11.7 5000.0 42.9 143.4 0.33 0.61 Ex.
(215) P2-103 5.5 12.2 5000.0 40.8 106.6 0.33 0.62 Ex. (216) P2-104
5.5 11.9 5000.0 42.0 100.8 0.33 0.61 Ex. (217) P2-105 5.4 11.7
5000.0 42.6 108.6 0.33 0.62 Ex. (218) P2-106 5.4 12.4 5000.0 40.2
138.3 0.33 0.62 Ex. (219) P2-107 5.5 12.1 5000.0 41.3 130.2 0.33
0.61 Ex. (220) P2-108 5.5 11.6 5000.0 43.0 111.0 0.33 0.62 Ex.
(221) P2-109 5.5 12.2 5000.0 41.0 126.4 0.33 0.62 Ex. (222) P2-110
5.4 11.6 5000.0 43.1 120.7 0.33 0.61 Ex. (223) P2-111 5.4 12.2
5000.0 41.0 107.3 0.33 0.61 Ex. (224) P2-112 5.5 12.4 5000.0 40.2
138.3 0.33 0.61 Ex. (225) P3-1 5.5 11.5 5000.0 43.3 128.1 0.33 0.62
Ex. (226) P3-2 5.5 12.1 5000.0 41.3 143.0 0.33 0.62 Ex. (227) P3-3
5.3 11.4 5000.0 43.9 96.3 0.33 0.61 Ex. (228) P3-4 5.4 12.2 5000.0
41.0 105.8 0.33 0.62 Ex. (229) P3-5 5.4 12.0 5000.0 41.7 145.1 0.33
0.62 Ex. (230) P3-6 5.5 11.6 5000.0 42.9 124.4 0.33 0.61 Ex. (231)
P3-19 5.5 10.1 5000.0 49.4 148.0 0.33 0.61 Ex. (232) P3-20 5.3 10.4
5000.0 48.1 94.6 0.33 0.61 Ex. (233) P3-21 5.4 10.4 5000.0 48.1
107.8 0.33 0.62 Ex. (234) P3-22 5.4 10.6 5000.0 47.3 104.9 0.33
0.62 Ex. (235) P3-23 5.4 10.9 5000.0 45.7 112.1 0.33 0.61 Ex. (236)
P3-24 5.5 10.2 5000.0 48.9 144.6 0.33 0.62 Ex. (237) P3-37 5.5 10.4
5000.0 48.1 99.5 0.33 0.62 Ex. (238) P3-38 5.4 11.4 5000.0 44.0
110.6 0.33 0.61
[0258] It can be seen from the results in Table 4 above, that the
OLEDs employing the inventive compounds as a hole transport layer
materials showed predominantly improved efficiency and lifespan,
compared to the OLEDs employing comparative compounds 1 to 4 as a
hole transport layer materials. Especially, it can be seen that the
OLEDs employing the inventive compounds showed predominantly
improved efficiency and lifespan, compared to the Comparative
Example 1 employing comparative compound 1 of which structure is
different from the inventive compound.
[0259] Further, referring to the Comparative Example 2 to 4
employing comparative compounds 2 to 4 that have carbazole as core
as the structure in the present invention, the OLED employing
comparative compound 2 where a linker is linked to 2-position of
the carbazole moiety (`Com. Ex(3) and `Com. Ex(4)`) showed higher
drive voltage and shorter life span yet higher efficiency, compared
to the OLED employing comparative compounds where a linker is
linked to 3-position of the carbazole moiety (`Com. Ex(2)).
Comparing OLEDs employing the inventive compounds having a
non-linear phenyl linker and the OLED of Com. Ex(4) having a
non-linear biphenyl linker, the efficiency of OLEDs employing the
inventive compounds is higher than the OLED of Com. Ex(4).
[0260] From the result in Table 4, it is seen that the OLEDs
employing as a hole transport layer material, the compound of the
present invention wherein the linker phenyl is linked to 2-position
of carbazole derivative and an amine group is linked on ortho- or
meta-position of the phenyl, showed high efficiency, compared to
the OLED of Com. Ex (4) wherein the linker biphenyl is linked to
2-position of carbazole derivative and the amine group is linked to
biphenyl on meta position.
[0261] These results are believed to come from that in a compound
where the linker is linked on 2-position of the carbazole core, the
conjugation length gets shorter than in a compound where the linker
is linked on 3-position of the carbazole core, and the band gap
gets widened and the HOMO value gets deepen.
[0262] Further, it is seen that where an amine group is linked on
ortho- or meta-position of a linker and the linker is not biphenyl
but phenyl as the inventive invention, the bonding angle gets
decreased than in a case where the amine group is linked linear to
the linker on para-position, and the T1 values get higher, and as a
result the electron blocking abilities are improved.
[0263] Therefore, the OLED employing the inventive compound as a
hole transport layer material has deep HOMO values and the improved
electron blocking abilities, and as a result the exciton is more
easily produced to improve efficiency and lengthen lifespan.
[0264] Considering the characteristics (deep HOMO energy level,
high T1 value, heat-stability) described above together, it can be
seen that the band gap and electrical properties, as well as the
surface properties can change much depending on the linking
position of the carbazole core and the amine, and which the linker
is phenyl or biphenyl, which can be main factors in improving
performance of the organic electric elements.
[0265] Furthermore, properties from the hole transport layer should
be considered in relation with the light emitting layer (host), and
one skilled in the art, even using a similar core compound, would
have difficulty in inferring the characteristics shown by the hole
transport layer using the compound of the present invention.
[Example 239] an Emission-Auxiliary Layer (Red)
[0266] Organic light emitting diodes (OLEDs) were fabricated
according to a conventional method by using a compound of the
present invention as an emission-auxiliary layer material.
[0267] First, an ITO layer (anode) was formed on a glass substrate,
and a film of 2-TNATA was vacuum-deposited on the ITO layer to form
a hole injection layer with a thickness of 60 nm. Subsequently,
N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine
("NPD") was vacuum-deposited with a thickness of 60 nm on the hole
injection layer to form a hole transport layer.
[0268] Subsequently, a film of the compound P1-1 of the present
invention was vacuum-deposited on the hole transport layer to form
a emission-auxiliary layer with a thickness of 20 nm.
[0269] A light emitting layer with a thickness of 30 nm was
deposited on the emission-auxiliary layer by using the CBP as a
host material and
bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate
("(piq).sub.2Ir(acac)") as a dopant material in a weight ratio of
95:5.
[0270] Next, a film of BAlq was vacuum-deposited with a thickness
of 10 nm on the light emitting layer to form a hole blocking layer,
and a film of Alq.sub.3 was formed with a thickness of 40 nm to
form an electron transport layer.
[0271] Next, LiF as halogenated alkali metal was deposited with a
thickness of 0.2 nm on the electron transport layer to form an
electron injection layer, and then Al was deposited with a
thickness of 150 nm on the electron injection layer to form a
cathode. In this way, the OLED was completed.
[Example 240] to [Example 365] an Emission-Auxiliary Layer
(Red)
[0272] The OLED was manufactured in the same manner as described in
Test Example 239, except that any one of the compounds P1-2 to
P1-20, P1-45 to P1-52, P1-61 to P1-64, P1-101 to P1-108, P2-1 to
P2-20, P2-45 to P2-52, P2-61 to P2-64, P2-101 to P2-108, P3-1 to
P3-38, P4-2, P4-5, P4-8 to P4-10, P4-17, P4-20, P4-22 and P4-24 of
the present invention in the Table 5 below was used as the
emission-auxiliary layer material, instead of the inventive
compound P1-1.
Comparative Example 5
[0273] An OLED was manufactured in the same manner as described in
Test Example 239, except that Comparative Compound 2 above was used
as the emission-auxiliary layer material, instead of the inventive
compound P1-1.
Comparative Example 6
[0274] An OLED was manufactured in the same manner as described in
Test Example 239, except that Comparative Compound 3 above was used
as the emission-auxiliary layer material, instead of the inventive
compound P1-1.
Comparative Example 7
[0275] An OLED was manufactured in the same manner as described in
Test Example 239, except that Comparative Compound 4 above was used
as the emission-auxiliary layer material, instead of the inventive
compound P1-1.
Comparative Example 8
[0276] An OLED was manufactured in the same manner as described in
Test Example 239, except not to form the emission-auxiliary
layer.
[0277] A forward bias DC voltage was applied to each of the OLEDs
manufactured through Test Examples 239 to 365 and Comparative
Examples 5 to 8, and electro-luminescence (EL) characteristics of
the OLED were measured by PR-650 (Photoresearch). Also, T95 life
span was measured by life span measuring equipment (Mcscience) at a
reference brightness of 2500 cd/m.sup.2. Table 5 below shows
evaluation results of OLEDs manufactured Test Examples and
Comparative Examples.
TABLE-US-00005 TABLE 5 Current Voltage Density Brightness
Efficiency Lifetime CIE Compound (V) (mA/cm.sup.2) (cd/m.sup.2)
(cd/A) T(95) x y Com. Ex (5) Com. Com (2) 5.9 26.5 2500.0 9.5 95.4
0.65 0.31 Com. Ex (6) Com. Com (3) 6.0 27.7 2500.0 9.0 96.1 0.64
0.34 Com. Ex (7) Com. Com (4) 6.1 26.4 2500.0 9.5 91.4 0.66 0.33
Com. Ex (8) -- 5.7 33.3 2500.0 7.5 71.3 0.64 0.31 Ex. (239) P1-1
5.7 23.5 2500.0 10.7 117.6 0.64 0.32 Ex. (240) P1-2 5.6 22.7 2500.0
11.0 116.9 0.65 0.31 Ex. (241) P1-3 5.6 19.5 2500.0 12.8 117.1 0.66
0.32 Ex. (242) P1-4 5.6 19.4 2500.0 12.9 115.1 0.66 0.30 Ex. (243)
P1-5 5.7 24.7 2500.0 10.1 116.9 0.66 0.32 Ex. (244) P1-6 5.6 19.7
2500.0 12.7 119.8 0.64 0.30 Ex. (245) P1-7 5.6 21.1 2500.0 11.8
116.2 0.66 0.33 Ex. (246) P1-8 5.6 19.8 2500.0 12.6 115.1 0.65 0.30
Ex. (247) P1-9 5.7 24.7 2500.0 10.1 110.0 0.65 0.31 Ex. (248) P1-10
5.7 24.4 2500.0 10.2 117.0 0.66 0.33 Ex. (249) P1-11 5.7 20.7
2500.0 12.1 115.9 0.65 0.32 Ex. (250) P1-12 5.6 21.9 2500.0 11.4
116.2 0.65 0.30 Ex. (251) P1-13 5.6 24.0 2500.0 10.4 114.4 0.65
0.34 Ex. (252) P1-14 5.7 23.7 2500.0 10.6 112.4 0.64 0.34 Ex. (253)
P1-15 5.7 19.4 2500.0 12.9 111.6 0.64 0.31 Ex. (254) P1-16 5.7 22.1
2500.0 11.3 114.8 0.65 0.32 Ex. (255) P1-17 5.6 22.1 2500.0 11.3
111.2 0.65 0.30 Ex. (256) P1-18 5.7 20.6 2500.0 12.2 112.2 0.66
0.32 Ex. (257) P1-19 5.6 22.0 2500.0 11.3 112.4 0.64 0.31 Ex. (258)
P1-20 5.6 22.3 2500.0 11.2 112.0 0.66 0.31 Ex. (259) P1-45 5.7 21.6
2500.0 11.6 111.0 0.65 0.30 Ex. (260) P1-46 5.6 20.0 2500.0 12.5
113.9 0.64 0.31 Ex. (261) P1-47 5.6 20.9 2500.0 12.0 110.8 0.64
0.31 Ex. (262) P1-48 5.6 19.3 2500.0 13.0 117.2 0.65 0.33 Ex. (263)
P1-49 5.6 25.0 2500.0 10.0 110.2 0.65 0.34 Ex. (264) P1-50 5.7 20.7
2500.0 12.1 118.1 0.64 0.31 Ex. (265) P1-51 5.6 19.8 2500.0 12.6
113.1 0.65 0.31 Ex. (266) P1-52 5.7 22.4 2500.0 11.1 116.0 0.65
0.31 Ex. (267) P1-61 5.7 24.2 2500.0 10.3 116.4 0.65 0.33 Ex. (268)
P1-62 5.6 23.8 2500.0 10.5 116.2 0.66 0.31 Ex. (269) P1-63 5.6 23.1
2500.0 10.8 115.0 0.64 0.33 Ex. (270) P1-64 5.7 20.5 2500.0 12.2
111.3 0.64 0.31 Ex. (271) P1-101 5.6 20.9 2500.0 12.0 119.3 0.64
0.31 Ex. (272) P1-102 5.7 19.7 2500.0 12.7 113.9 0.65 0.30 Ex.
(273) P1-103 5.7 23.8 2500.0 10.5 116.8 0.65 0.34 Ex. (274) P1-104
5.7 19.5 2500.0 12.8 116.2 0.66 0.33 Ex. (275) P1-105 5.6 20.3
2500.0 12.3 116.7 0.66 0.31 Ex. (276) P1-106 5.7 22.9 2500.0 10.9
119.3 0.65 0.31 Ex. (277) P1-107 5.7 21.1 2500.0 11.9 115.2 0.66
0.32 Ex. (278) P1-108 5.6 23.9 2500.0 10.5 116.1 0.65 0.33 Ex.
(279) P2-1 5.7 24.4 2500.0 10.3 118.8 0.65 0.33 Ex. (280) P2-2 5.6
22.4 2500.0 11.1 117.7 0.65 0.32 Ex. (281) P2-3 5.6 20.6 2500.0
12.1 119.9 0.65 0.31 Ex. (282) P2-4 5.7 20.5 2500.0 12.2 111.9 0.64
0.30 Ex. (283) P2-5 5.7 22.2 2500.0 11.3 115.8 0.65 0.33 Ex. (284)
P2-6 5.6 19.7 2500.0 12.7 113.5 0.66 0.31 Ex. (285) P2-7 5.6 19.3
2500.0 12.9 112.6 0.64 0.31 Ex. (286) P2-8 5.6 21.0 2500.0 11.9
111.7 0.66 0.30 Ex. (287) P2-9 5.7 23.2 2500.0 10.8 118.4 0.65 0.31
Ex. (288) P2-10 5.6 20.9 2500.0 12.0 117.3 0.66 0.30 Ex. (289)
P2-11 5.7 24.9 2500.0 10.0 111.8 0.65 0.33 Ex. (290) P2-12 5.6 19.4
2500.0 12.9 116.1 0.66 0.34 Ex. (291) P2-13 5.6 20.6 2500.0 12.1
119.4 0.66 0.31 Ex. (292) P2-14 5.6 20.6 2500.0 12.1 114.0 0.65
0.34 Ex. (293) P2-15 5.6 20.6 2500.0 12.1 116.0 0.65 0.32 Ex. (294)
P2-16 5.6 23.2 2500.0 10.8 114.7 0.65 0.32 Ex. (295) P2-17 5.6 22.6
2500.0 11.0 114.2 0.64 0.30 Ex. (296) P2-18 5.6 24.5 2500.0 10.2
114.1 0.66 0.32 Ex. (297) P2-19 5.7 21.5 2500.0 11.6 113.9 0.66
0.30 Ex. (298) P2-20 5.6 20.1 2500.0 12.5 112.6 0.64 0.31 Ex. (299)
P2-45 5.7 23.5 2500.0 10.6 116.1 0.66 0.30 Ex. (300) P2-46 5.6 23.3
2500.0 10.7 115.0 0.64 0.33 Ex. (301) P2-47 5.6 21.1 2500.0 11.9
112.1 0.66 0.33 Ex. (302) P2-48 5.6 21.8 2500.0 11.5 118.8 0.65
0.32 Ex. (303) P2-49 5.6 20.2 2500.0 12.4 114.8 0.65 0.32 Ex. (304)
P2-50 5.7 22.9 2500.0 10.9 119.3 0.64 0.31 Ex. (305) P2-51 5.7 19.8
2500.0 12.6 119.3 0.65 0.33 Ex. (306) P2-52 5.7 21.5 2500.0 11.6
115.3 0.65 0.33 Ex. (307) P2-61 5.7 19.9 2500.0 12.6 115.2 0.66
0.32 Ex. (308) P2-62 5.7 22.0 2500.0 11.3 111.6 0.66 0.31 Ex. (309)
P2-63 5.6 20.0 2500.0 12.5 111.5 0.65 0.31 Ex. (310) P2-64 5.7 24.9
2500.0 10.0 113.3 0.64 0.32 Ex. (311) P2-101 5.7 23.7 2500.0 10.5
115.6 0.65 0.31 Ex. (312) P2-102 5.7 23.6 2500.0 10.6 118.9 0.65
0.32 Ex. (313) P2-103 5.7 20.4 2500.0 12.3 113.0 0.65 0.31 Ex.
(314) P2-104 5.7 22.3 2500.0 11.2 116.4 0.66 0.33 Ex. (315) P2-105
5.7 23.7 2500.0 10.6 110.5 0.66 0.34 Ex. (316) P2-106 5.7 24.3
2500.0 10.3 115.3 0.66 0.31 Ex. (317) P2-107 5.7 21.6 2500.0 11.6
110.9 0.65 0.33 Ex. (318) P2-108 5.6 21.6 2500.0 11.6 111.9 0.66
0.34 Ex. (319) P3-1 5.5 17.5 2500.0 14.3 128.9 0.65 0.32 Ex. (320)
P3-2 5.6 17.6 2500.0 14.2 129.4 0.65 0.32 Ex. (321) P3-3 5.6 16.8
2500.0 14.9 127.3 0.66 0.32 Ex. (322) P3-4 5.6 17.5 2500.0 14.3
123.5 0.66 0.31 Ex. (323) P3-5 5.5 17.1 2500.0 14.7 127.8 0.66 0.32
Ex. (324) P3-6 5.5 17.3 2500.0 14.4 123.9 0.65 0.34 Ex. (325) P3-7
5.5 17.6 2500.0 14.2 128.1 0.66 0.33 Ex. (326) P3-8 5.6 17.4 2500.0
14.3 126.5 0.65 0.30 Ex. (327) P3-9 5.6 17.4 2500.0 14.4 123.9 0.65
0.32 Ex. (328) P3-10 5.6 16.8 2500.0 14.9 126.3 0.65 0.30 Ex. (329)
P3-11 5.5 17.6 2500.0 14.2 129.8 0.64 0.32 Ex. (330) P3-12 5.6 17.4
2500.0 14.3 123.4 0.65 0.32 Ex. (331) P3-13 5.5 17.1 2500.0 14.7
127.5 0.65 0.34 Ex. (332) P3-14 5.6 17.5 2500.0 14.3 125.8 0.66
0.34 Ex. (333) P3-15 5.6 17.4 2500.0 14.4 120.3 0.65 0.32 Ex. (334)
P3-16 5.6 17.5 2500.0 14.3 124.3 0.65 0.31 Ex. (335) P3-17 5.6 17.2
2500.0 14.6 121.3 0.65 0.34 Ex. (336) P3-18 5.6 17.6 2500.0 14.2
124.6 0.66 0.31 Ex. (337) P3-19 5.6 17.1 2500.0 14.6 129.0 0.64
0.30 Ex. (338) P3-20 5.6 17.1 2500.0 14.6 125.9 0.65 0.33 Ex. (339)
P3-21 5.5 17.5 2500.0 14.3 123.6 0.65 0.34 Ex. (340) P3-22 5.6 17.0
2500.0 14.7 122.6 0.65 0.31 Ex. (341) P3-23 5.5 17.3 2500.0 14.5
124.0 0.65 0.32 Ex. (342) P3-24 5.5 16.7 2500.0 14.9 127.4 0.65
0.32 Ex. (343) P3-25 5.5 17.6 2500.0 14.2 121.1 0.65 0.31 Ex. (344)
P3-26 5.5 17.7 2500.0 14.1 127.2 0.66 0.34 Ex. (345) P3-27 5.6 17.7
2500.0 14.1 124.5 0.66 0.32 Ex. (346) P3-28 5.6 17.0 2500.0 14.7
121.5 0.65 0.31 Ex. (347) P3-29 5.5 17.1 2500.0 14.6 126.6 0.65
0.32 Ex. (348) P3-30 5.6 16.7 2500.0 14.9 128.7 0.65 0.32 Ex. (349)
P3-31 5.6 17.3 2500.0 14.4 129.9 0.65 0.34 Ex. (350) P3-32 5.6 17.3
2500.0 14.5 124.3 0.64 0.32 Ex. (351) P3-33 5.6 16.8 2500.0 14.9
127.0 0.65 0.30 Ex. (352) P3-34 5.5 17.2 2500.0 14.6 125.5 0.66
0.32 Ex. (353) P3-35 5.6 16.9 2500.0 14.7 123.8 0.64 0.33 Ex. (354)
P3-36 5.5 16.9 2500.0 14.8 127.7 0.66 0.31 Ex. (355) P3-37 5.5 16.7
2500.0 15.0 126.7 0.66 0.30 Ex. (356) P3-38 5.6 16.7 2500.0 15.0
125.3 0.65 0.31 Ex. (357) P4-2 5.0 12.8 2500.0 19.5 138.7 0.65 0.31
Ex. (358) P4-5 5.0 12.9 2500.0 19.4 132.7 0.65 0.32 Ex. (359) P4-8
5.1 13.2 2500.0 18.9 131.6 0.65 0.32 Ex. (360) P4-9 5.0 13.4 2500.0
18.6 132.7 0.65 0.31 Ex. (361) P4-10 5.0 13.8 2500.0 18.2 139.3
0.66 0.34 Ex. (362) P4-17 5.2 14.9 2500.0 16.8 132.5 0.66 0.32 Ex.
(363) P4-20 5.2 14.2 2500.0 17.6 131.0 0.65 0.31 Ex. (364) P4-22
5.3 14.6 2500.0 17.1 130.8 0.65 0.32 Ex. (365) P4-24 5.2 14.0
2500.0 17.8 136.4 0.65 0.32
[Example 366] an Emission-Auxiliary Layer (Green)
[0278] Organic light emitting diodes (OLEDs) were fabricated
according to a conventional method by using a compound of the
present invention as an emission-auxiliary layer material
[0279] First, an ITO layer (anode) was formed on a glass substrate,
and a film of 2-TNATA was vacuum-deposited on the ITO layer to form
a hole injection layer with a thickness of 60 nm. Subsequently, NPD
was vacuum-deposited with a thickness of 60 nm on the hole
injection layer to form a hole transport layer.
[0280] Subsequently, a film of the compound P1-21 of the present
invention was vacuum-deposited on the hole transport layer to form
a emission-auxiliary layer with a thickness of 20 nm. A light
emitting layer with a thickness of 30 nm was deposited on the
emission-auxiliary layer by using the CBP as a host material and
Ir(ppy).sub.3 as a dopant material in a weight ratio of 95:5.
[0281] Next, a film of BAlq was vacuum-deposited with a thickness
of 10 nm on the light emitting layer to form a hole blocking layer,
and a film of Alq.sub.3 was formed with a thickness of 40 nm to
form an electron transport layer.
[0282] Next, LiF as halogenated alkali metal was deposited with a
thickness of 0.2 nm on the electron transport layer to form an
electron injection layer, and then Al was deposited with a
thickness of 150 nm on the electron injection layer to form a
cathode. In this way, the OLED was completed.
[Example 367] to [Example 485] an Emission-Auxiliary Layer
(Green)
[0283] The OLED was manufactured in the same manner as described in
Test Example 366, except that any one of the compounds P1-22 to
P1-44, P1-77 to P1-112, P2-21 to P2-44, and P2-77 to P2-112 of the
present invention in the Table 6 below was used as the
emission-auxiliary layer material, instead of the inventive
compound P1-21.
Comparative Example 9
[0284] An OLED was manufactured in the same manner as described in
Test Example 366, except that Comparative Compound 2 above was used
as the emission-auxiliary layer material, instead of the inventive
compound P1-21.
Comparative Example 10
[0285] An OLED was manufactured in the same manner as described in
Test Example 366, except that Comparative Compound 3 above was used
as the emission-auxiliary layer material, instead of the inventive
compound P1-21.
Comparative Example 11
[0286] An OLED was manufactured in the same manner as described in
Test Example 366, except that Comparative Compound 4 above was used
as the emission-auxiliary layer material, instead of the inventive
compound P1-21.
Comparative Example 12
[0287] An OLED was manufactured in the same manner as described in
Test Example 366, except not to form the emission-auxiliary
layer.
[0288] A forward bias DC voltage was applied to each of the OLEDs
manufactured through Test Examples 366 to 485 and Comparative
Example 9 to 12, and electro-luminescence (EL) characteristics of
the OLED were measured by PR-650 (Photoresearch). Also, T95 life
span was measured by life span measuring equipment (Mcscience) at a
reference brightness of 5000 cd/m.sup.2. Table 6 below shows
evaluation results of OLEDs manufactured Test Examples and
Comparative Examples.
TABLE-US-00006 TABLE 6 Current Voltage Density Brightness
Efficiency Lifetime CIE Compound (V) (mA/cm.sup.2) (cd/m.sup.2)
(cd/A) T(95) x y Com. Ex (9) Com. Com (2) 5.6 13.6 5000.0 36.8
116.9 0.33 0.61 Com. Ex (10) Com. Com (3) 5.9 12.1 5000.0 41.2
116.5 0.33 0.61 Com. Ex (11) Com. Com (4) 6.2 11.4 5000.0 44.0
110.1 0.33 0.61 Com. Ex (12) -- 5.6 21.7 5000.0 23.0 65.7 0.33 0.61
Ex. (366) P1-21 6.1 10.4 5000.0 48.2 147.9 0.33 0.62 Ex. (367)
P1-22 5.8 10.2 5000.0 49.0 114.2 0.33 0.62 Ex. (368) P1-23 5.8 10.1
5000.0 49.3 104.8 0.33 0.61 Ex. (369) P1-24 5.8 10.1 5000.0 49.4
143.6 0.33 0.61 Ex. (370) P1-25 6.0 10.0 5000.0 49.8 126.5 0.33
0.62 Ex. (371) P1-26 5.9 10.1 5000.0 49.5 118.2 0.33 0.61 Ex. (372)
P1-27 5.9 10.3 5000.0 48.4 109.7 0.33 0.62 Ex. (373) P1-28 6.0 10.4
5000.0 48.3 131.0 0.33 0.62 Ex. (374) P1-29 5.8 10.4 5000.0 48.3
103.4 0.33 0.62 Ex. (375) P1-30 6.0 10.3 5000.0 48.8 116.9 0.33
0.61 Ex. (376) P1-31 6.1 10.4 5000.0 47.9 112.7 0.33 0.62 Ex. (377)
P1-32 6.1 10.1 5000.0 49.5 106.9 0.33 0.61 Ex. (378) P1-33 5.9 10.3
5000.0 48.6 104.9 0.33 0.62 Ex. (379) P1-34 5.7 10.5 5000.0 47.6
127.4 0.33 0.61 Ex. (380) P1-35 6.0 10.5 5000.0 47.4 126.6 0.33
0.61 Ex. (381) P1-36 5.8 10.1 5000.0 49.7 140.1 0.33 0.62 Ex. (382)
P1-37 5.7 10.3 5000.0 48.6 134.4 0.33 0.61 Ex. (383) P1-38 5.9 10.3
5000.0 48.4 142.4 0.33 0.61 Ex. (384) P1-39 6.1 10.2 5000.0 49.2
129.9 0.33 0.62 Ex. (385) P1-40 6.0 10.5 5000.0 47.6 140.4 0.33
0.61 Ex. (386) P1-41 6.0 10.4 5000.0 48.1 145.4 0.33 0.61 Ex. (387)
P1-42 5.9 10.3 5000.0 48.5 129.9 0.33 0.62 Ex. (388) P1-43 6.0 10.6
5000.0 47.1 118.9 0.33 0.61 Ex. (389) P1-44 6.1 10.6 5000.0 47.2
114.1 0.33 0.62 Ex. (390) P1-77 5.9 10.4 5000.0 48.1 126.6 0.33
0.62 Ex. (391) P1-78 6.0 10.2 5000.0 48.8 140.4 0.33 0.61 Ex. (392)
P1-79 6.2 10.2 5000.0 49.1 131.8 0.33 0.61 Ex. (393) P1-80 5.8 10.3
5000.0 48.4 130.1 0.33 0.61 Ex. (394) P1-81 6.2 10.4 5000.0 48.1
115.5 0.33 0.62 Ex. (395) P1-82 6.1 10.2 5000.0 48.9 143.7 0.33
0.62 Ex. (396) P1-83 6.2 10.5 5000.0 47.5 119.2 0.33 0.61 Ex. (397)
P1-84 5.9 10.0 5000.0 50.0 128.0 0.33 0.62 Ex. (398) P1-85 5.9 10.6
5000.0 47.1 132.9 0.33 0.61 Ex. (399) P1-86 5.8 10.1 5000.0 49.6
115.8 0.33 0.61 Ex. (400) P1-87 5.8 10.1 5000.0 49.6 137.4 0.33
0.61 Ex. (401) P1-88 5.8 10.4 5000.0 48.2 105.4 0.33 0.62 Ex. (402)
P1-89 5.8 10.5 5000.0 47.5 109.9 0.33 0.62 Ex. (403) P1-90 5.8 10.2
5000.0 49.0 104.9 0.33 0.61 Ex. (404) P1-91 6.1 10.1 5000.0 49.3
125.1 0.33 0.61 Ex. (405) P1-92 6.2 10.0 5000.0 49.8 109.0 0.33
0.61 Ex. (406) P1-93 6.0 10.6 5000.0 47.3 139.3 0.33 0.62 Ex. (407)
P1-94 6.1 10.1 5000.0 49.3 143.5 0.33 0.62 Ex. (408) P1-95 5.8 10.3
5000.0 48.3 148.4 0.33 0.62 Ex. (409) P1-96 6.2 10.2 5000.0 49.0
129.1 0.33 0.62 Ex. (410) P1-97 6.0 10.3 5000.0 48.5 120.9 0.33
0.62 Ex. (411) P1-98 5.8 10.6 5000.0 47.3 118.2 0.33 0.62 Ex. (412)
P1-99 6.0 10.4 5000.0 48.2 100.5 0.33 0.62 Ex. (413) P1-100 6.1
10.2 5000.0 49.0 110.1 0.33 0.61 Ex. (414) P1-101 5.8 10.6 5000.0
47.3 103.9 0.33 0.62 Ex. (415) P1-102 5.9 10.6 5000.0 47.4 118.9
0.33 0.62 Ex. (416) P1-103 5.9 10.3 5000.0 48.7 107.0 0.33 0.61 Ex.
(417) P1-104 6.2 10.6 5000.0 47.2 112.5 0.33 0.62 Ex. (418) P1-105
6.2 10.0 5000.0 49.9 110.3 0.33 0.62 Ex. (419) P1-106 5.9 10.2
5000.0 49.0 141.6 0.33 0.61 Ex. (420) P1-107 6.0 10.4 5000.0 47.9
108.6 0.33 0.62 Ex. (421) P1-108 5.8 10.2 5000.0 48.9 130.0 0.33
0.62 Ex. (422) P1-109 5.9 10.6 5000.0 47.4 132.4 0.33 0.62 Ex.
(423) P1-110 5.7 10.4 5000.0 48.3 132.7 0.33 0.61 Ex. (424) P1-111
5.9 10.0 5000.0 49.8 140.1 0.33 0.61 Ex. (425) P1-112 6.2 10.1
5000.0 49.7 124.7 0.33 0.62 Ex. (426) P2-21 5.7 9.5 5000.0 52.4
149.6 0.33 0.61 Ex. (427) P2-22 6.0 9.1 5000.0 54.7 101.9 0.33 0.61
Ex. (428) P2-23 6.0 9.1 5000.0 54.8 103.2 0.33 0.61 Ex. (429) P2-24
6.1 9.4 5000.0 53.4 125.4 0.33 0.61 Ex. (430) P2-25 6.0 9.2 5000.0
54.2 141.2 0.33 0.62 Ex. (431) P2-26 6.0 9.3 5000.0 54.0 116.4 0.33
0.61 Ex. (432) P2-27 6.1 9.5 5000.0 52.6 138.5 0.33 0.61 Ex. (433)
P2-28 6.0 9.4 5000.0 53.1 132.0 0.33 0.61 Ex. (434) P2-29 6.0 9.9
5000.0 50.4 133.6 0.33 0.61 Ex. (435) P2-30 6.0 9.6 5000.0 52.2
117.4 0.33 0.61 Ex. (436) P2-31 6.0 9.2 5000.0 54.2 149.9 0.33 0.61
Ex. (437) P2-32 6.0 9.7 5000.0 51.4 105.8 0.33 0.62 Ex. (438) P2-33
5.7 9.7 5000.0 51.8 135.1 0.33 0.62 Ex. (439) P2-34 6.1 9.5 5000.0
52.7 127.6 0.33 0.62 Ex. (440) P2-35 5.9 9.3 5000.0 54.0 137.8 0.33
0.62 Ex. (441) P2-36 5.8 9.7 5000.0 51.7 115.8 0.33 0.61 Ex. (442)
P2-37 6.0 9.4 5000.0 53.4 142.9 0.33 0.61 Ex. (443) P2-38 6.0 9.6
5000.0 52.1 144.4 0.33 0.61 Ex. (444) P2-39 6.0 9.5 5000.0 52.4
126.3 0.33 0.62 Ex. (445) P2-40 5.8 9.5 5000.0 52.6 128.5 0.33 0.61
Ex. (446) P2-41 5.8 9.6 5000.0 52.3 109.2 0.33 0.61 Ex. (447) P2-42
5.7 9.9 5000.0 50.7 129.7 0.33 0.62 Ex. (448) P2-43 6.0 9.5 5000.0
52.7 110.0 0.33 0.61 Ex. (449) P2-44 6.0 9.9 5000.0 50.5 141.9 0.33
0.62 Ex. (450) P2-77 6.0 9.1 5000.0 54.7 128.6 0.33 0.62 Ex. (451)
P2-78 5.7 9.9 5000.0 50.5 109.1 0.33 0.61 Ex. (452) P2-79 6.1 9.1
5000.0 54.9 100.5 0.33 0.62 Ex. (453) P2-80 6.0 9.9 5000.0 50.6
132.8 0.33 0.62 Ex. (454) P2-81 5.8 9.7 5000.0 51.3 141.8 0.33 0.61
Ex. (455) P2-82 5.9 9.7 5000.0 51.3 148.1 0.33 0.61 Ex. (456) P2-83
5.9 9.2 5000.0 54.1 141.2 0.33 0.61 Ex. (457) P2-84 5.8 9.3 5000.0
53.6 142.6 0.33 0.61 Ex. (458) P2-85 5.8 9.6 5000.0 52.3 129.5 0.33
0.61 Ex. (459) P2-86 6.0 9.2 5000.0 54.5 127.9 0.33 0.62 Ex. (460)
P2-87 6.1 9.6 5000.0 52.3 112.8 0.33 0.61 Ex. (461) P2-88 5.8 9.4
5000.0 53.4 119.6 0.33 0.62 Ex. (462) P2-89 6.0 9.4 5000.0 53.2
101.3 0.33 0.62 Ex. (463) P2-90 5.9 9.6 5000.0 52.3 148.0 0.33 0.62
Ex. (464) P2-91 5.7 9.8 5000.0 50.9 136.2 0.33 0.62 Ex. (465) P2-92
5.8 9.2 5000.0 54.2 103.4 0.33 0.61 Ex. (466) P2-93 6.0 9.1 5000.0
54.8 137.7 0.33 0.62 Ex. (467) P2-94 5.8 9.8 5000.0 51.1 131.6 0.33
0.62 Ex. (468) P2-95 6.0 9.7 5000.0 51.7 144.1 0.33 0.62 Ex. (469)
P2-96 5.7 9.3 5000.0 53.6 109.9 0.33 0.62 Ex. (470) P2-97 6.0 9.8
5000.0 50.9 120.6 0.33 0.62 Ex. (471) P2-98 6.0 9.1 5000.0 54.8
139.7 0.33 0.62 Ex. (472) P2-99 5.9 9.3 5000.0 53.9 125.5 0.33 0.62
Ex. (473) P2-100 6.0 9.3 5000.0 53.7 127.2 0.33 0.61 Ex. (474)
P2-101 6.1 9.4 5000.0 53.3 137.4 0.33 0.62 Ex. (475) P2-102 6.2 9.9
5000.0 50.7 136.5 0.33 0.61 Ex. (476) P2-103 6.2 9.3 5000.0 53.5
115.7 0.33 0.62 Ex. (477) P2-104 6.1 9.8 5000.0 51.2 119.4 0.33
0.61 Ex. (478) P2-105 5.7 10.0 5000.0 50.0 125.9 0.33 0.61 Ex.
(479) P2-106 6.1 9.2 5000.0 54.3 143.8 0.33 0.62 Ex. (480) P2-107
5.8 9.9 5000.0 50.4 105.0 0.33 0.62 Ex. (481) P2-108 5.8 9.7 5000.0
51.5 107.6 0.33 0.61 Ex. (482) P2-109 5.8 9.2 5000.0 54.3 136.8
0.33 0.62 Ex. (483) P2-110 5.9 9.4 5000.0 53.3 121.4 0.33 0.62 Ex.
(484) P2-111 5.7 9.6 5000.0 52.0 134.9 0.33 0.62 Ex. (485) P2-112
5.9 9.7 5000.0 51.6 136.1 0.33 0.62
[0289] It can be seen from the results in Tables 5 and 6 above,
that the OLEDs using the inventive compounds as the auxiliary
emission layer material showed predominantly improved efficiency
and lifespan, compared to the OLEDs using comparative compounds 2
to 4 as the auxiliary emission layer material and the OLEDs not
having the auxiliary emission layer.
[0290] That is, the OLEDs using the present invention compounds
showed predominantly improved efficiency and long life span,
compared to the OLEDs not forming the auxiliary emission layer, and
the OLEDs using comparative compounds 2 to 4 as the auxiliary
emission layer material.
[0291] Especially, comparing the case that OLEDs employ comparative
compounds 3 and 4 and the case that OLEDs employ the inventive
compounds, it can be seen that significant difference in efficiency
and life span was shown between the compounds having a linker
equally linked to the same 2-position of the carbazole cores yet
the substituent amine group is linked on a different position of
the linker. This is believed because different bonding angle occurs
depending on to which position of the linker the amine group is
linked, so does the different T1 values, which causes different
electron blocking abilities.
[0292] In addition, referring to Table 5 showing the result in
OLEDs comprising red auxiliary emission layer, it can be seen that
although efficiency and driving voltage are similar or slightly
increased, life span is improved where compounds (P3-1 to P3-38) of
the present invention having R.sup.3 being a substituent other than
hydrogen are used as a red auxiliary emission layer, compared to
the compounds having R.sup.3 being hydrogen. It is inferred that
this result is caused because when the layer of OLED is formed,
packing density, Hole injection and mobility are dependent on the
kinds of substituent R.sup.3.
[0293] Further, the case that the inventive compounds
(P4-2.about.24) of which Ar.sup.2 is carbazole derivatives among
the inventive compounds are employed as red auxiliary emission
layer materials showed the best results, especially, showed
predominantly improved efficiency and driving voltage. These
results are believed to come from that heat-degradation in the
interfacial between ITO and a hole transport layer is decreased and
heat the life span of the organic elements is improved because the
abilities of a hole injection and a hole mobility are improved by
comprising another carbazole derivatives in the inventive compound,
and the driving voltage, efficiency and life span are optimized
because charge balance between a hole and an electron in a light
emitting layer is increased and the light emitting is well made in
the light emitting layer not the interfacial of the hole transport
layer by transferring more holes to the light emitting layer.
[0294] Furthermore, in compounds (P4-2.about.10) where Ar.sup.2 is
a carbazole derivatives and Ar.sup.2 is linked to L (linker) on
ortho position, the driving voltage of the organic element gets
lower than in compounds (P4-17.about.24) where Ar.sup.2 is a
carbazole derivatives and Ar.sup.2 is linked to L (linker) on meta
position, because packing density of the compound where Ar.sup.2 is
linked to L (linker) on ortho position gets well during
deposition.
[0295] As described above, it was shown that the linking position
of between the carbazole core and the linker substituted with a
amine group, between the linker and the amine group, and the kind
of the linker is important factor because the performance ability
of the organic elements in an auxiliary emission layer as well as a
hole transport layer changes depending on the linking position and
the kind of the linker.
[0296] Although exemplary embodiments of the present invention have
been described for illustrative purposes, those skilled in the art
will appreciate that various modifications, additions and
substitutions are possible, without departing from the scope and
spirit of the invention as disclosed in the accompanying claims.
Therefore, the embodiment disclosed in the present invention is
intended to illustrate the scope of the technical idea of the
present invention, and the scope of the present invention is not
limited by the embodiment. The scope of the present invention shall
be construed on the basis of the accompanying claims, and it shall
be construed that all of the technical ideas included within the
scope equivalent to the claims belong to the present invention.
* * * * *