U.S. patent application number 13/171986 was filed with the patent office on 2011-10-27 for compound for organic photoelectric device, organic photoelectric device including the same, and display device including the same.
Invention is credited to Mi-Young Chae, Kyu-Yeol In, Ho-Kuk Jung, Eui-Su Kang, Myeong-Soon Kang, Nam-Soo Kim, Jin-Seong Park.
Application Number | 20110260153 13/171986 |
Document ID | / |
Family ID | 42310706 |
Filed Date | 2011-10-27 |
United States Patent
Application |
20110260153 |
Kind Code |
A1 |
In; Kyu-Yeol ; et
al. |
October 27, 2011 |
COMPOUND FOR ORGANIC PHOTOELECTRIC DEVICE, ORGANIC PHOTOELECTRIC
DEVICE INCLUDING THE SAME, AND DISPLAY DEVICE INCLUDING THE
SAME
Abstract
A compound for an organic photoelectric device, an organic
photoelectric device including the same, and a display device
including the same the compound being represented by the following
Chemical Formula 1: ##STR00001##
Inventors: |
In; Kyu-Yeol; (Uiwang-si,
KR) ; Kang; Myeong-Soon; (Uiwang-si, KR) ;
Jung; Ho-Kuk; (Uiwang-si, KR) ; Kim; Nam-Soo;
(Uiwang-si, KR) ; Kang; Eui-Su; (Uiwang-si,
KR) ; Chae; Mi-Young; (Uiwang-si, KR) ; Park;
Jin-Seong; (Uiwang-si, KR) |
Family ID: |
42310706 |
Appl. No.: |
13/171986 |
Filed: |
June 29, 2011 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
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PCT/KR2009/007521 |
Dec 16, 2009 |
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13171986 |
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Current U.S.
Class: |
257/40 ;
257/E51.024; 546/256; 548/131 |
Current CPC
Class: |
C09K 11/06 20130101;
H01L 51/5012 20130101; C07D 417/04 20130101; C07D 417/10 20130101;
H05B 33/10 20130101; C07D 413/10 20130101; H01L 51/0071 20130101;
H01L 51/007 20130101; C07D 403/10 20130101; C09B 1/00 20130101;
C09K 2211/1037 20130101; H01L 51/0072 20130101; H01L 2251/308
20130101; C09K 2211/1044 20130101; C09B 57/001 20130101; H01L
51/0058 20130101; C09K 2211/1029 20130101; H01L 51/0054 20130101;
C09K 2211/1096 20130101; C09K 2211/1007 20130101; C09K 2211/1059
20130101; C09K 2211/1011 20130101; C09K 2211/1033 20130101; H01L
51/0052 20130101; H01L 51/5072 20130101; C09K 2211/1048 20130101;
C09B 57/00 20130101; H01L 51/0067 20130101 |
Class at
Publication: |
257/40 ; 546/256;
548/131; 257/E51.024 |
International
Class: |
H01L 51/54 20060101
H01L051/54; C07D 413/10 20060101 C07D413/10; C07D 401/14 20060101
C07D401/14; C07D 413/14 20060101 C07D413/14; C07D 417/14 20060101
C07D417/14 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 30, 2008 |
KR |
10-2008-0137222 |
Claims
1. A compound for an organic photoelectric device, the compound
being represented by the following Chemical Formula 1: ##STR00085##
wherein, in Chemical Formula 1, A.sub.1 to A.sub.5 are each
independently selected from the group of CR.sub.1 to CR.sub.5 and
N, provided that three or less of A.sub.1 to A.sub.5 are N, R.sub.1
to R.sub.5 are each independently selected from the group of
hydrogen, a halogen, a nitrile, a cyano, a nitro, an amide, a
carbonyl, an ester, a substituted or unsubstituted alkyl, a
substituted or unsubstituted alkoxy, a substituted or unsubstituted
alkenyl, a substituted or unsubstituted cycloalkyl, a substituted
or unsubstituted aryl, a substituted or unsubstituted arylamine, a
substituted or unsubstituted heteroarylamine, a substituted or
unsubstituted heterocycle, a substituted or unsubstituted amino,
BR.sub.6R.sub.7, and SiR.sub.6R.sub.7R.sub.8, R.sub.6 to R.sub.8
are each independently selected from the group of a substituted or
unsubstituted alkyl and a substituted or unsubstituted aryl, when
only one of A.sub.1 to A.sub.5 is N, the remaining four of A.sub.1
to A.sub.5 are respectively selected from the group of CR.sub.1 to
CR.sub.5, provided that at least two of R.sub.1 to R.sub.5 are not
hydrogen, when A.sub.1 to A.sub.5 are respectively CR.sub.1 to
CR.sub.5, at least two of R.sub.1 to R.sub.5 are not hydrogen, Z is
selected from the group of O, S, Se, and NR'', U and D are each
independently selected from the group of CR' and N, provided that
when Z is O, S, or Se, U is N, R' and R'' are each independently
selected from the group of hydrogen, a halogen, a nitrile, a cyano,
a nitro, an amide, a carbonyl, an ester, a substituted or
unsubstituted alkyl, a substituted or unsubstituted alkoxy, a
substituted or unsubstituted alkenyl, a substituted or
unsubstituted cycloalkyl, a substituted or unsubstituted aryl, a
substituted or unsubstituted arylamine, a substituted or
unsubstituted heteroarylamine, a substituted or unsubstituted
heterocycle, a substituted or unsubstituted amino, BR.sub.6R.sub.7,
and SiR.sub.6R.sub.7R.sub.3, E is selected from the group of
hydrogen, a nitrile, a cyano, a nitro, an amide, a carbonyl, a
substituted or unsubstituted alkyl, a substituted or unsubstituted
fluoroalkyl, a substituted or unsubstituted cycloalkyl, a
substituted or unsubstituted aryl, a substituted or unsubstituted
heterocycle, and SO.sub.2R.sub.9, R.sub.9 is selected from the
group of a nitrile, a cyano, a nitro, an amide, a carbonyl, a
substituted or unsubstituted alkyl, a substituted or unsubstituted
cycloalkyl, a substituted or unsubstituted aryl, and a substituted
or unsubstituted heterocycle, L is selected from the group of a
substituted or unsubstituted arylene and a substituted or
unsubstituted heteroarylene, and n is 0 or 1.
2. The compound as claimed in claim 1, wherein the compound has an
asymmetric structure such that upper and lower substituents are
different from each other with respect to an axis including
A.sub.3.
3. The compound as claimed in claim 1, wherein: A.sub.1 and A.sub.5
are different from each other, and A.sub.2 and A.sub.4 are
different from each other.
4. The compound as claimed in claim 1, wherein, in Chemical Formula
1, R.sub.1, R.sub.1', and R.sub.1'' are each independently a
substituted or unsubstituted C6 to C40 aryl.
5. The compound as claimed in claim 1, wherein, in Chemical Formula
1, R.sub.1, R.sub.1', and R.sub.1'' are each independently an
arylamine, the arylamine including one of a diphenyl amine, a
dinaphthyl amine, a dibiphenyl amine, a phenyl naphthyl amine, a
phenyl diphenyl amine, a ditolyl amine, a phenyl tolyl amine, a
carbazolyl, and a triphenyl amine.
6. The compound as claimed in claim 1, wherein, in Chemical Formula
1, R.sub.1, R.sub.1', and R.sub.1'' are each independently a
substituted or unsubstituted heterocycle, the substituted or
unsubstituted heterocycle including one of a thiophenyl, a furanyl,
a pyrrolyl, an imidazolyl, a thiazolyl, an oxazolyl, an
oxadiazolyl, a triazolyl, a pyridinyl, a pyridazinyl, a quinolinyl,
an isoquinolinine, an acridyl, an imidazopyridinyl, and an
imidazopyrimidinyl.
7. The compound as claimed in claim 1, wherein, in Chemical Formula
1, R.sub.1, R.sub.1', and R.sub.1'' are each independently a
substituted imidazolyl or a substituted triazolyl, the substituent
thereof: being linked to nitrogen (N) of the imidazolyl or
triazolyl, and including one of a substituted or unsubstituted
alkyl, a substituted or unsubstituted cycloalkyl, a substituted or
unsubstituted aryl, and a substituted or unsubstituted
heterocycle.
8. The compound as claimed in claim 1, wherein, in Chemical Formula
1: one of R.sub.1, R.sub.1', and R.sub.1'' is substituted with a
substituent, the substituent including one of an amine-substituted
alkyl, an amine-substituted cycloalkyl, an amine-substituted aryl,
and an amine-substituted heterocycle, and another of R.sub.1,
R.sub.1', and R.sub.1'' is substituted with a substituent, the
substituent including one of a nitrile, a nitrile, a nitro, an
amide, a carbonyl, and a heterocycle.
9. A compound for an organic photoelectric device, the compound
being represented by the following Chemical Formula 112:
##STR00086## wherein, in Chemical Formula 112, A.sub.1 to A.sub.12
are each independently selected from the group of CR.sub.1 to
CR.sub.12 and N, provided that at least one of A.sub.7 to A.sub.12
is N, and R.sub.1 to R.sub.6 adjacent to each other optionally form
a fused ring, and R.sub.7 to R.sub.12 adjacent to each other
optionally form a fused ring, X is selected from the group of O, S,
Se, and NR.sub.13, and Y is CR.sub.14 or N, provided that when X is
selected from the group of O, S, and Se, Y is N, L is a substituted
or unsubstituted C6 to C50 arylene, a is 0 or 1, provided that when
a is 0, A.sub.1 to A.sub.6 are each independently CR.sub.1 to
CR.sub.6, and when a is 1, at least one of A.sub.1 to A.sub.6 is N,
b and c are each independently an integer of 1 to 3, and R.sub.1 to
R.sub.14 are each independently selected from the group of
hydrogen, a halogen, a nitrile, a cyano, a nitro, an amide, a
carbonyl, an ester, a substituted or unsubstituted alkyl, a
substituted or unsubstituted alkylene, a substituted or
unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a
substituted or unsubstituted alkenylene, a substituted or
unsubstituted alkynyl, a substituted or unsubstituted alkynylene, a
substituted or unsubstituted cycloalkyl, a substituted or
unsubstituted cycloalkylene, a substituted or unsubstituted aryl, a
substituted or unsubstituted arylene, a substituted or
unsubstituted arylamine, a substituted or unsubstituted
heteroarylamine, a substituted or unsubstituted heterocycle, a
substituted or unsubstituted amino, BRR', or SiRR'R'', wherein R,
R' and R'' are the same or different, and each independently a
substituted or unsubstituted alkyl, or a substituted or
unsubstituted aryl.
10. The compound as claimed in claim 9, wherein in Chemical Formula
112: one of R.sub.7 to R.sub.12 is substituted with a substituent
selected from the group of an amine-substituted alkyl, an
amine-substituted cycloalkyl, an amine substituted aryl, and an
amine-substituted heterocycle, and one of R.sub.1 to R.sub.6 is
substituted with a substituent selected from the group of a
nitrile, a nitro, an amide, a carbonyl, and a substituted or
unsubstituted heterocycle.
11. The compound as claimed in claim 9, wherein the compound is
represented by the following Chemical Formula 113: ##STR00087##
wherein, in Chemical Formula 113, A.sub.2, A.sub.4 to A.sub.12 and
A.sub.7' to A.sub.12' are each independently selected from the
group of CR.sub.2, CR.sub.4 to CR.sub.12, CR.sub.7' to CR.sub.12'
and N, provided at least one of A.sub.7 to A.sub.12 is N, and at
least one of A.sub.7' to A.sub.12' is N, wherein R.sub.4 to R.sub.6
adjacent to each other optionally form a fused ring, R.sub.7 to
R.sub.12 adjacent to each other optionally form a fused ring, and
R.sub.7' to R.sub.12' adjacent to each other optionally form a
fused ring, X is selected from the group of O, S, Se, and
NR.sub.13, and Y is CR.sub.14 or N, provided that when X is
selected from the group of O, S, and Se, Y is N, L and L' are each
independently a substituted or unsubstituted C6 to C50 arylene, a
and a' are each independently 0 or 1, provided that when a and a'
are each independently 0, A.sub.2, A.sub.4 to A.sub.6 are each
independently CR.sub.2 and CR.sub.4 to CR.sub.6, and when a and a'
are each independently 1, at least one of A, and A.sub.4 to A.sub.6
is N, b and b' are each independently an integer of 1 to 3, and
R.sub.2, R.sub.4 to R.sub.14, and R.sub.7' to R.sub.12' are each
independently hydrogen, a halogen, a nitrile, a cyano, a nitro, an
amide, a carbonyl, an ester, a substituted or unsubstituted alkyl,
a substituted or unsubstituted alkylene, a substituted or
unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a
substituted or unsubstituted alkenylene, a substituted or
unsubstituted alkynyl, a substituted or unsubstituted alkynylene, a
substituted or unsubstituted cycloalkyl, a substituted or
unsubstituted cycloalkylene, a substituted or unsubstituted aryl, a
substituted or unsubstituted arylene, a substituted or
unsubstituted arylamine, a substituted or unsubstituted
heteroarylamine, a substituted or unsubstituted heterocycle, a
substituted or unsubstituted amino, BRR', or SiRR'R'', wherein R,
R' and R'' are the same or different, and each independently a
substituted or unsubstituted alkyl, or a substituted or
unsubstituted aryl.
12. The compound as claimed in claim 9, wherein, in Chemical
Formula 112, R.sub.1 to R.sub.14 are each independently an
arylamine, the arylamine including one of a diphenyl amine, a
dinaphthyl amine, a dibiphenyl amine, a phenyl naphthyl amine, a
phenyl diphenyl amine, a ditolyl amine, a phenyl tolyl amine, a
carbazolyl, and a triphenyl amine.
13. The compound as claimed in claim 9, wherein, in Chemical
Formula 112, R.sub.1 to R.sub.14 are each independently a
substituted or unsubstituted heterocycle, the substituted or
unsubstituted heterocycle including one of a thiophenyl, a furanyl,
a pyrrolyl, an imidazolyl, a thiazolyl, an oxazolyl, an
oxadiazolyl, a triazolyl, a pyridinyl, a pyridazinyl, a quinolinyl,
an isoquinolinine, an acridyl, an imidazopyridinyl, and an
imidazopyrimidinyl.
14. An organic photoelectric device, comprising: an anode, a
cathode, and at least one organic thin layer between the anode and
cathode, wherein the at least one organic thin layer includes the
compound as claimed in claim 1.
15. The organic photoelectric device as claimed in claim 14,
wherein the compound is a host material or a charge transport
material.
16. The organic photoelectric device as claimed in claim 14,
wherein the at least one organic thin layer includes one of an
emission layer, an electron transport layer (ETL), an electron
injection layer (EIL), a hole transport layer (HTL), a hole
injection layer (HIL), and a hole blocking layer.
17. The organic photoelectric device as claimed in claim 14,
wherein the at least one organic thin layer further includes a
reducing dopant.
18. The organic photoelectric device as claimed in claim 17,
wherein the reducing dopant includes one of an alkaline metal, an
alkaline earth metal, a rare earth element metal, an oxide of an
alkaline metal, a halide of an alkaline metal, an organic complex
of an alkaline metal, an oxide of an alkaline earth metal, a halide
of an alkaline earth metal, an organic complex of an alkaline earth
metal, an oxide of an alkaline earth metal, a halide of an alkaline
earth metal, an organic complex of an alkaline earth metal, an
oxide of a rare earth element metal, a halide of a rare earth
element metal, and an organic complex of a rare earth element
metal.
19. A display device comprising an organic photoelectric device as
claimed in claim 14.
20. An organic photoelectric device, comprising: an anode, a
cathode, and at least one organic thin layer between the anode and
cathode, wherein the at least one organic thin layer includes the
compound as claimed in claim 9.
Description
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This application is a continuation of pending International
Application No. PCT/KR2009/007521, entitled "Novel Compound for
Organic Photoelectric Device and Organic Photoelectric Device
Including the Same," which was filed on Dec. 16, 2009, which is
incorporated herein by reference in its entirety.
BACKGROUND
[0002] 1. Field
[0003] Embodiments relate to a compound for an organic
photoelectric device, an organic photoelectric device including the
same, and a display device including the same.
[0004] 2. Description of the Related Art
[0005] An organic photoelectric device transforms electrical energy
into light by applying current to an organic light emitting
material. It has a structure in which a functional organic material
layer is interposed between an anode and a cathode.
[0006] The organic light emitting diode has similar electrical
characteristics to those of light emitting diodes (LEDs) in which
holes are injected from an anode and electrons are injected from a
cathode, then the holes and electrons move to opposite electrodes
and are recombined to form excitons having high energy. The
excitons generate light having a certain wavelength while shifting
to a ground state.
[0007] Light emission of an anthracene organic material was first
discovered in 1960, but was found have a high driving voltage. A
polymer light emitting diode may use poly(p-phenylenevinylene)
(PPV). Research has been conducted on a low molecular weight light
emitting element (SMOLED) and a polymer organic light emitting
diode (POLED). The low molecular organic light emitting diode may
be manufactured as a thin film in a vacuum deposition method, and
may have good efficiency and life-span performance. A polymer
organic light emitting diode may be manufactured by an Inkjet or
spin coating method and may have an advantage of low initial cost
and being large-sized.
SUMMARY
[0008] Embodiments are directed to a compound for an organic
photoelectric device, an organic photoelectric device including the
same, and a display device including the same.
[0009] The embodiments may be realized by providing a compound for
an organic photoelectric device, the compound being represented by
the following Chemical Formula 1:
##STR00002##
[0010] wherein, in Chemical Formula 1, A.sub.1 to A.sub.5 are each
independently selected from the group of CR.sub.1 to CR.sub.5 and
N, provided that three or less of A.sub.1 to A.sub.5 are N, R.sub.1
to R.sub.5 are each independently selected from the group of
hydrogen, a halogen, a nitrile, a cyano, a nitro, an amide, a
carbonyl, an ester, a substituted or unsubstituted alkyl, a
substituted or unsubstituted alkoxy, a substituted or unsubstituted
alkenyl, a substituted or unsubstituted cycloalkyl, a substituted
or unsubstituted aryl, a substituted or unsubstituted arylamine, a
substituted or unsubstituted heteroarylamine, a substituted or
unsubstituted heterocycle, a substituted or unsubstituted amino,
BR.sub.6R.sub.7, and SiR.sub.6R.sub.7R.sub.8, R.sub.6 to R.sub.8
are each independently selected from the group of a substituted or
unsubstituted alkyl and a substituted or unsubstituted aryl, when
only one of A.sub.1 to A.sub.5 is N, the remaining four of A.sub.1
to A.sub.5 are respectively selected from the group of CR.sub.1 to
CR.sub.5, provided that at least two of R.sub.1 to R.sub.5 are not
hydrogen, when A.sub.1 to A.sub.5 are respectively CR.sub.1 to
CR.sub.5, at least two of R.sub.1 to R.sub.5 are not hydrogen, Z is
selected from the group of O, S, Se, and NR'', U and D are each
independently selected from the group of CR' and N, provided that
when Z is O, S, or Se, U is N, R' and R'' are each independently
selected from the group of hydrogen, a halogen, a nitrile, a cyano,
a nitro, an amide, a carbonyl, an ester, a substituted or
unsubstituted alkyl, a substituted or unsubstituted alkoxy, a
substituted or unsubstituted alkenyl, a substituted or
unsubstituted cycloalkyl, a substituted or unsubstituted aryl, a
substituted or unsubstituted arylamine, a substituted or
unsubstituted heteroarylamine, a substituted or unsubstituted
heterocycle, a substituted or unsubstituted amino, BR.sub.6R.sub.7,
and SiR.sub.6R.sub.7R.sub.8, E is selected from the group of
hydrogen, a nitrile, a cyano, a nitro, an amide, a carbonyl, a
substituted or unsubstituted alkyl, a substituted or unsubstituted
fluoroalkyl, a substituted or unsubstituted cycloalkyl, a
substituted or unsubstituted aryl, a substituted or unsubstituted
heterocycle, and SO.sub.2R.sub.9, R.sub.9 is selected from the
group of a nitrile, a cyano, a nitro, an amide, a carbonyl, a
substituted or unsubstituted alkyl, a substituted or unsubstituted
cycloalkyl, a substituted or unsubstituted aryl, and a substituted
or unsubstituted heterocycle, L is selected from the group of a
substituted or unsubstituted arylene and a substituted or
unsubstituted heteroarylene, and n is 0 or 1.
[0011] The compound may be represented by the following Chemical
Formula 112:
##STR00003##
[0012] wherein, in Chemical Formula 112, A.sub.1 to A.sub.12 are
each independently selected from the group of CR.sub.1 to CR.sub.12
and N, provided that at least one of A.sub.7 to A.sub.12 is N, and
R.sub.1 to R.sub.6 adjacent to each other optionally form a fused
ring, and R.sub.7 to R.sub.12 adjacent to each other optionally
form a fused ring, X is selected from the group of O, S, Se, and
NR.sub.13, and Y is CR.sub.14 or N, provided that when X is
selected from the group of O, S, and Se, Y is N, L is a substituted
or unsubstituted C6 to C50 arylene, a is 0 or 1, provided that when
a is 0, A.sub.1 to A.sub.6 are each independently CR.sub.1 to
CR.sub.6, and when a is 1, at least one of A.sub.1 to A.sub.6 is N,
b and c are each independently an integer of 1 to 3, and R.sub.1 to
R.sub.14 are each independently selected from the group of
hydrogen, a halogen, a nitrile, a cyano, a nitro, an amide, a
carbonyl, an ester, a substituted or unsubstituted alkyl, a
substituted or unsubstituted alkylene, a substituted or
unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a
substituted or unsubstituted alkenylene, a substituted or
unsubstituted alkynyl, a substituted or unsubstituted alkynylene, a
substituted or unsubstituted cycloalkyl, a substituted or
unsubstituted cycloalkylene, a substituted or unsubstituted aryl, a
substituted or unsubstituted arylene, a substituted or
unsubstituted arylamine, a substituted or unsubstituted
heteroarylamine, a substituted or unsubstituted heterocycle, a
substituted or unsubstituted amino, BRR', or SiRR'R'', wherein R,
R' and R'' are the same or different, and each independently a
substituted or unsubstituted alkyl, or a substituted or
unsubstituted aryl.
[0013] In Chemical Formula 112 one of R.sub.7 to R.sub.12 may be
substituted with a substituent selected from the group of an
amine-substituted alkyl, an amine-substituted cycloalkyl, an amine
substituted aryl, and an amine-substituted heterocycle, and one of
R.sub.1 to R.sub.6 may be substituted with a substituent selected
from the group of a nitrile, a nitro, an amide, a carbonyl, and a
substituted or unsubstituted heterocycle.
[0014] The compound may be represented by the following Chemical
Formula 113:
##STR00004##
[0015] wherein, in Chemical Formula 113, A.sub.2, A.sub.4 to
A.sub.12 and A.sub.7' to A.sub.12' are each independently selected
from the group of CR.sub.2, CR.sub.4 to CR.sub.12, CR.sub.7' to
CR.sub.12' and N, provided at least one of A.sub.7 to A.sub.12 is
N, and at least one of A.sub.7' to A.sub.12' is N, wherein R.sub.4
to R.sub.6 adjacent to each other optionally form a fused ring,
R.sub.7 to R.sub.12 adjacent to each other optionally form a fused
ring, and R.sub.7' to R.sub.12' adjacent to each other optionally
form a fused ring, X is selected from the group of O, S, Se, and
NR.sub.13, and Y is CR.sub.14 or N, provided that when X is
selected from the group of O, S, and Se, Y is N, L and L' are each
independently a substituted or unsubstituted C6 to C50 arylene, a
and a' are each independently 0 or 1, provided that when a and a'
are each independently 0, A.sub.2, A.sub.4 to A.sub.6 are each
independently CR.sub.2 and CR.sub.4 to CR.sub.6, and when a and a'
are each independently 1, at least one of A, and A.sub.4 to A.sub.6
is N, b and b' are each independently an integer of 1 to 3, and
R.sub.2, R.sub.4 to R.sub.14, and R.sub.7' to R.sub.12' are each
independently hydrogen, a halogen, a nitrile, a cyano, a nitro, an
amide, a carbonyl, an ester, a substituted or unsubstituted alkyl,
a substituted or unsubstituted alkylene, a substituted or
unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a
substituted or unsubstituted alkenylene, a substituted or
unsubstituted alkynyl, a substituted or unsubstituted alkynylene, a
substituted or unsubstituted cycloalkyl, a substituted or
unsubstituted cycloalkylene, a substituted or unsubstituted aryl, a
substituted or unsubstituted arylene, a substituted or
unsubstituted arylamine, a substituted or unsubstituted
heteroarylamine, a substituted or unsubstituted heterocycle, a
substituted or unsubstituted amino, BRR', or SiRR'R'', wherein R,
R' and R'' are the same or different, and each independently a
substituted or unsubstituted alkyl, or a substituted or
unsubstituted aryl.
[0016] The compound may have an asymmetric structure such that
upper and lower substituents are different from each other with
respect to an axis including A.sub.3.
[0017] A.sub.1 and A.sub.5 may be different from each other, and
A.sub.2 and A.sub.4 may be different from each other.
[0018] In Chemical Formula 1, R.sub.1, R.sub.1', and R.sub.1'' may
each independently be a substituted or unsubstituted C6 to C40
aryl.
[0019] In Chemical Formula 1, R.sub.1, R.sub.1', and R.sub.1'' may
each independently be an arylamine, the arylamine including one of
a diphenyl amine, a dinaphthyl amine, a dibiphenyl amine, a phenyl
naphthyl amine, a phenyl diphenyl amine, a ditolyl amine, a phenyl
tolyl amine, a carbazolyl, and a triphenyl amine.
[0020] In Chemical Formula 1, R.sub.1, R.sub.1', and R.sub.1'' may
each independently be a substituted or unsubstituted heterocycle,
the substituted or unsubstituted heterocycle including one of a
thiophenyl, a furanyl, a pyrrolyl, an imidazolyl, a thiazolyl, an
oxazolyl, an oxadiazolyl, a triazolyl, a pyridinyl, a pyridazinyl,
a quinolinyl, an isoquinolinine, an acridyl, an imidazopyridinyl,
and an imidazopyrimidinyl.
[0021] In Chemical Formula 1, R.sub.1, R.sub.1', and R.sub.1'' may
each independently be a substituted imidazolyl or a substituted
triazolyl, the substituent thereof being linked to nitrogen (N) of
the imidazolyl or triazolyl, and including one of a substituted or
unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a
substituted or unsubstituted aryl, and a substituted or
unsubstituted heterocycle.
[0022] In Chemical Formula 1, one of R.sub.1, R.sub.1', and
R.sub.1'' may be substituted with a substituent, the substituent
including one of an amine-substituted alkyl, an amine-substituted
cycloalkyl, an amine-substituted aryl, and an amine-substituted
heterocycle, and another of R.sub.1, R.sub.1', and R.sub.1'' may be
substituted with a substituent, the substituent including one of a
nitrile, a nitrile, a nitro, an amide, a carbonyl, and a
heterocycle.
[0023] The embodiments may also be realized by providing an organic
photoelectric device including an anode, a cathode, and at least
one organic thin layer between the anode and cathode, wherein the
at least one organic thin layer includes the compound according to
an embodiment.
[0024] The compound may be a host material or a charge transport
material.
[0025] The at least one organic thin layer may include one of an
emission layer, an electron transport layer (ETL), an electron
injection layer (EIL), a hole transport layer (HTL), a hole
injection layer (HIL), and a hole blocking layer.
[0026] The at least one organic thin layer may further include a
reducing dopant.
[0027] The reducing dopant may include one of an alkaline metal, an
alkaline earth metal, a rare earth element metal, an oxide of an
alkaline metal, a halide of an alkaline metal, an organic complex
of an alkaline metal, an oxide of an alkaline earth metal, a halide
of an alkaline earth metal, an organic complex of an alkaline earth
metal, an oxide of an alkaline earth metal, a halide of an alkaline
earth metal, an organic complex of an alkaline earth metal, an
oxide of a rare earth element metal, a halide of a rare earth
element metal, and an organic complex of a rare earth element
metal.
[0028] The embodiments may also be realized by providing a display
device including an organic photoelectric device according to an
embodiment.
BRIEF DESCRIPTION OF THE DRAWINGS
[0029] The embodiments will become more apparent to those of
ordinary skill in the art by describing in detail exemplary
embodiments with reference to the attached drawings, in which:
[0030] FIGS. 1 to 5 illustrate cross-sectional views of organic
photoelectric devices including organic compounds according to
various embodiments.
[0031] FIGS. 6-14 illustrate .sup.1H NMR spectra of compounds
according to Examples 1 to 9, respectively.
[0032] FIG. 15 illustrates a graph showing voltage-luminescence
characteristics of organic light emitting diodes according to
Examples 10 to 13 and Comparative Example 2.
[0033] FIG. 16 illustrates a graph showing voltage-luminescence
characteristics of organic light emitting diodes according to
Examples 14 to 16 and Comparative Example 2.
[0034] FIG. 17 illustrates a graph showing electrical power
efficiency of the organic light emitting diodes according to
Examples 10 to 13 and Comparative Example 2.
[0035] FIG. 18 illustrates a graph showing electrical power
efficiency of the organic light emitting diodes according to
Examples 14 to 16 and Comparative Example 2.
[0036] FIG. 19 illustrates a graph showing thermal properties of
the compound according to Example 5.
[0037] FIG. 20 illustrates a graph showing thermal properties of
the compound according to Comparative Example 1.
DETAILED DESCRIPTION
[0038] This application claims the benefits of priority of Korean
Patent Application No. 10-2008-0137222, filed on Dec. 30, 2008, in
the Korean Intellectual Property Office, which is incorporated by
reference herein in its entirety.
[0039] Example embodiments will now be described more fully
hereinafter with reference to the accompanying drawings; however,
they may be embodied in different forms and should not be construed
as limited to the embodiments set forth herein. Rather, these
embodiments are provided so that this disclosure will be thorough
and complete, and will fully convey the scope of the invention to
those skilled in the art.
[0040] In the drawing figures, the dimensions of layers and regions
may be exaggerated for clarity of illustration. It will also be
understood that when a layer or element is referred to as being
"on" another layer or substrate, it can be directly on the other
layer or substrate, or intervening layers may also be present.
Further, it will be understood that when a layer is referred to as
being "under" another layer, it can be directly under, and one or
more intervening layers may also be present. In addition, it will
also be understood that when a layer is referred to as being
"between" two layers, it can be the only layer between the two
layers, or one or more intervening layers may also be present. Like
reference numerals refer to like elements throughout.
[0041] As used herein, when specific definition is not provided,
the term "alkyl" may refer to a C1 to C30 alkyl, and preferably a
C1 to C15 alkyl; the term "alkoxy" may refer to a C1 to 30 alkoxy,
and preferably a C1 to C15 alkoxy; the term "alkenyl" may refer to
a C 2 to C30 alkenyl, and preferably a C2 to C15 alkenyl; the term
"cycloalkyl" may refer to a C 3 to C30 cycloalkyl, and preferably a
C3 to C15 cycloalkyl; the term "aryl" may refer to a C 6 to C50
aryl, and preferably a C6 to C25 aryl; the term "arylamine" may
refer to a C 7 to C50 arylamine, and preferably a C7 to C25
arylamine; the term "heteroarylamine" may refer to a C7 to C50
heteroarylamine, and preferably a C7 to C25 hetero arylamine; the
term "heterocycle" may refer to a C5 to C50 heterocycle, and
preferably a C5 to C25 heterocycle; and the term "fluoroalkyl" may
refer to a C 1 to C10 fluoroalkyl.
[0042] As used herein, when a definition is not otherwise provided,
the term "ester" may refer to --COOR; and the term "carbonyl" may
refer to --COR'. Herein R and R' may each independently be
hydrogen, a C1 to C10 alkyl, a C6 to C20 aryl, a C3 to C20
cycloalkyl, a C2 to C10 alkenyl, a C2 to C10 alkynyl, or a
combination thereof.
[0043] As used herein, when specific definition is not otherwise
provided, the term "substituted" may refer to one substituted with
at least a substituent selected from the group of a halogen, a
nitrile, a cyano, a nitro, an amide, a carbonyl, an acetylene, a C1
to C10 alkyl, a C2 to C10 alkenyl, a C1 to C10alkoxy, a C6 to
C20arylamine, a C6 to C20aryl, a C6 to C20arylalkyl, a C6 to
C20arylalkenyl, a C2 to C20heterocycle, a C1 to C20amine, a C3 to
C20 cycloalkyl, BR.sub.6R.sub.7, and SiR.sub.6R.sub.7R.sub.8, where
R.sub.6 to R.sub.8 are each independently selected from the group
of a C1 to C30 alkyl and a C6 to C50 aryl.
[0044] As used herein, when a definition is not otherwise provided,
the prefix "hetero" may refer to one including 1 to 3, including N,
O, S, or P, in one ring.
[0045] As used herein, when specific definition is not provided,
the term "heterocycle" may refer to one selected from the group of
a C5 to C50 heteroaryl, a C5 to C50 heterocycloalkyl, a C5 to C50
heterocycloalkenyl, a C5 to C50 heterocycloalkynyl, and fused rings
thereof. The heterocycle preferably includes 1 to 20 heteroatoms,
and more preferably 1 to 15 heteroatoms.
[0046] An embodiment provides a compound for an organic
photoelectric device, the compound being represented by the
following Formula 1:
##STR00005##
[0047] In Chemical Formula 1, A.sub.1 to A.sub.5 may each
independently be selected from the group of CR.sub.1 to CR.sub.5
and N, provided that three or less of A.sub.1 to A.sub.5 are N.
R.sub.1 to R.sub.5, R', and R'' (R' and R'' being described in
greater detail below) may each independently be selected from the
group of hydrogen, a halogen, a nitrile, a cyano, a nitro, an
amide, a carbonyl, an ester, a substituted or unsubstituted alkyl,
a substituted or unsubstituted alkoxy, a substituted or
unsubstituted alkenyl, a substituted or unsubstituted cycloalkyl, a
substituted or unsubstituted aryl, a substituted or unsubstituted
arylamine, a substituted or unsubstituted heteroarylamine, a
substituted or unsubstituted heterocycle, a substituted or
unsubstituted amino, BR.sub.6R.sub.7, and SiR.sub.6R.sub.7R.sub.8.
R.sub.6 to R.sub.8 may each independently be selected from the
group of a substituted or unsubstituted alkyl and a substituted or
unsubstituted aryl.
[0048] When only one of A.sub.1 to A.sub.5 is N, the remaining four
of A.sub.1 to A.sub.5 may be respectively selected from the group
of CR.sub.1 to CR.sub.5, provided that at least two of R.sub.1 to
R.sub.5 are not hydrogen, and
[0049] when A.sub.1 to A.sub.5 are respectively CR.sub.1 to
CR.sub.5, at least two of R.sub.1 to R.sub.5 are not hydrogen.
[0050] Z may be selected from the group of O, S, Se, and NR''.
[0051] U and D may each independently be selected from the group of
CR' and N, provided that when Z is O, S, or Se, U is N.
[0052] E may be selected from the group of hydrogen, a nitrile, a
cyano, a nitro, an amide, a carbonyl, a substituted or
unsubstituted alkyl, a substituted or unsubstituted fluoroalkyl, a
substituted or unsubstituted cycloalkyl, a substituted or
unsubstituted aryl, a substituted or unsubstituted heterocycle, and
SO.sub.2R.sub.9, and R.sub.9 may be selected from the group of a
nitrile, a cyano, a nitro, an amide, a carbonyl, a substituted or
unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a
substituted or unsubstituted aryl, and a substituted or
unsubstituted heterocycle.
[0053] L may be selected from the group of a substituted or
unsubstituted arylene and a substituted or unsubstituted
heteroarylene, and n may be 0 or 1.
[0054] The compound for an organic photoelectric device of the
above Chemical Formula 1 may include a part including A.sub.1 to
A.sub.5, a linking group of L including an arylene group or a
heteroarylene group, and a functional substitutent including a
five-member ring.
[0055] As noted above, A.sub.1 to A.sub.5 may each independently be
CR.sub.1 to CR.sub.5 or N, provided that three or fewer of A.sub.1
to A.sub.5 are N. When any one among A.sub.1 to A.sub.5 is N, the
LUMO (lowest unoccupied molecular orbital) energy level may be
lowered and electron affinity of a molecule may be increased.
Accordingly, injection and transport characteristics of electrons
may be improved. Thus, voltage required for driving an organic
light emitting diode may be reduced and electrical power efficiency
may be improved. However, when more than four among A.sub.1 to
A.sub.5 are N, too low a LUMO energy level may occur such that it
may be difficult to inject electrons.
[0056] For example, when any one among A.sub.1 to A.sub.5 is N,
four among A.sub.1 to A.sub.5 may respectively be selected from the
group of CR.sub.1 to CR.sub.5. Here, at least two of the R.sub.1 to
R.sub.5 may not be hydrogen. When at least one of the R.sub.1 to
R.sub.5 is not hydrogen but is a substituent, rigidity of the
compound may be increased and crystallization may easily occur.
When the R.sub.1 to R.sub.5 are all hydrogen, thermal stability may
be decreased and injection of electrons may be difficult.
[0057] When A.sub.1 to A.sub.5 are all substituted with N, A.sub.1
to A.sub.5 may be selected from the group of CR.sub.1 to CR.sub.5.
Here, at least two of the R.sub.1 to R.sub.5 may not be hydrogen.
When at least one of the R.sub.1 to R.sub.5 is not hydrogen but is
a substituent, rigidity of the compound may be increased. When the
R.sub.1 to R.sub.5 are all hydrogen, thermal stability may be
decreased, and it may also be difficult to inject electrons.
[0058] For example, when at least two of the R.sub.1 to R.sub.5 are
not hydrogen (but rather are a substituent), an amorphous
characteristic may be increased by introducing a different
substituent into a position of the substituent. Accordingly,
crystallization (caused by the Joule heat generated from a device
during the operation) may be suppressed and life-span
characteristic of an organic light emitting diode may be
improved.
[0059] In an implementation, A.sub.1 and A.sub.5 may be different
from each other, and A.sub.2 and A.sub.4 may be different from each
other. For example, the compound according to an embodiment may
have an asymmetric structure where upper and lower substituents are
different from each other with respect to an axis including
A.sub.3. This asymmetric structure may fortify the amorphous
characteristic and may suppress crystallization. Thus, life-span
characteristics may be improved when an organic photoelectric
device is driven. In addition, driving voltage of the organic
photoelectric device may be decreased and an organic photoelectric
device having excellent effects in terms of efficiency and thermal
stability may be provided.
[0060] The linking group, L (including an arylene group or a
heteroarylene group) may increase intermolecular interaction, and
thereby improve thermal stability. In addition, L may adjust the
.pi.-conjugation length and also light emitting in a visual region.
Accordingly, the compound according to an embodiment may be
usefully applied to an emission layer.
[0061] In addition, Z (in the functional substituent including a
five-member ring) may be selected from the group of O, S, Se, and
NR'', and U and D are different or the same. U and D may be
independently selected from the group of CR' and N. However, when Z
is not NR'', e.g., when Z is O, S, or Se, then U is N. The
functional substituent including a five-member ring may make the
structure of the compound generally asymmetric and may thereby
provide the compound with thermal stability.
[0062] In Chemical Formula 1, R.sub.1 to R.sub.5, R', and R'' may
each independently be aryls, and it is preferable that the aryls
are substituted or unsubstituted C6 to C40 aryls. When the aryls
are monocyclic aryls, e.g., phenyl, biphenyl, terphenyl, styrene,
and so on, or polycyclic aryls, e.g., naphthyl, anthracenyl,
phenanthrenyl, pyrenyl, peryenyl, and so on, the compound may be
useful for a material of an emission layer.
[0063] In an implementation, R.sub.1 to R.sub.5, R', and R'' may
each independently be an arylamine. The arylamine is preferably
selected from the group of diphenyl amine, dinaphthyl amine,
dibiphenyl amine, phenyl naphthyl amine, phenyl diphenyl amine,
ditolyl amine, phenyl tolyl amine, carbazolyl, and triphenyl
amine.
[0064] In an implementation, R.sub.1 to R.sub.5, R', and R'' may
each independently be a substituted or unsubstituted heterocycle,
and the heterocycle may be selected from the group of thiophenyl,
furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl,
triazolyl, pyridinyl, pyridazinyl, quinolinyl, isoquinolinine,
acridyl, imidazopyridinyl, and imidazopyrimidinyl.
[0065] When the substituted or unsubstituted heterocycle is an
imidazolyl or a triazolyl, the substituent linked to nitrogen (N)
of the imidazolyl or triazolyl may be selected from the group of a
substituted or unsubstituted alkyl such as a substituted or
unsubstituted methyl, a substituted or unsubstituted ethyl, a
substituted or unsubstituted propyl, a substituted or unsubstituted
isopropyl, a substituted or unsubstituted butyl, a substituted or
unsubstituted t-butyl, a substituted or unsubstituted pentyl, a
substituted or unsubstituted hexyl, and a substituted or
unsubstituted heptyl; a substituted or unsubstituted cycloalkyl
such as a substituted or unsubstituted cyclopentyl, a substituted
or unsubstituted cyclohexyl, and so on; a substituted or
unsubstituted aryl such as a substituted or unsubstituted phenyl, a
substituted or unsubstituted biphenyl, a substituted or
unsubstituted naphthyl, and so on; and a substituted or
unsubstituted heterocycle. The heterocycle is preferably a
heteroaryl, e.g., pyridyl, bipyridyl, quinolyl, isoquinolyl, and so
on.
[0066] In an implementation, R.sub.1 to R.sub.5, R', and R'' may be
functional groups having excellent electron injection
characteristics or functional groups being capable of improving
thermal stability. The functional groups may selectively provide
the compounds with hole injection/transport capabilities and
electron injection/transport capabilities, and thus may enable
efficient hole-electron combination in an emission layer.
[0067] For example, when one of R.sub.1 to R.sub.5, R', and R''
includes a substituent selected from the group of an
amine-substituted alkyl, an amine-substituted cycloalkyl, an
amine-substituted aryl, and an amine-substituted heterocycle, the
compound may be useful for a material of a hole injection layer
(HIL) and a hole transport layer (HTL).
[0068] When one of R.sub.1 to R.sub.5, R', and R'' includes a
substituent having excellent electron affinity selected from the
group of a nitrile, a nitro, an amide, a carbonyl, and a
heterocycle, the compound may be useful for a material of an
electron injection layer (EIL) or an electron transport layer
(ETL).
[0069] In an implementation, when one of R.sub.1 to R.sub.5, R',
and R'' includes a substituent selected from the group of an
amine-substituted alkyl, an amine-substituted cycloalkyl, an
amine-substituted aryl, and an amine-substituted heterocycle,
another of R.sub.1 to R.sub.5, R', and R'' may include a
substituent having excellent electron affinity selected from the
group of a nitrile, a nitro, an amide, a carbonyl, and a
heterocycle, the compound has both hole transport and electron
transport capabilities. A preferable amine-substituted heterocycle
is an amine-substituted heteroaryl, and a preferable heterocycle is
a heteroaryl.
[0070] In an implementation, when one of E and R'' includes a
substituent selected from the group of an amine-substituted alkyl,
an amine-substituted cycloalkyl, an amine-substituted aryl, and an
amine-substituted heterocycle, and the other of E and R'' includes
a nitrile, a nitro, an amide, a carbonyl, and a heterocycle,
amorphous characteristics may be more improved and hole and
electron transport characteristics may be finely controlled. A
preferable amine-substituted heterocycle is an amine-substituted
heteroaryl, and a preferable heterocycle is a heteroaryl.
[0071] L is preferably selected from the group of a substituted or
unsubstituted C6 to C30 arylene and a substituted or unsubstituted
C5 to C30 heteroarylene.
[0072] The various substituents of the above-described compound
represented by the above Chemical Formula 1 may not change
principal properties of the compound for an organic photoelectric
device according to an embodiment.
[0073] Examples of compounds for an organic photoelectric device
according to an embodiment may include compounds represented by the
following Chemical Formulae 2 to 111, but are not limited
thereto.
##STR00006## ##STR00007## ##STR00008## ##STR00009## ##STR00010##
##STR00011## ##STR00012## ##STR00013## ##STR00014## ##STR00015##
##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020##
##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025##
##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030##
##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035##
##STR00036##
[0074] In an implementation, the compound for an organic
photoelectric device may be represented by the following Chemical
Formula 112 and may include sequentially repeated aryls and
heterocycles.
##STR00037##
[0075] In Chemical Formula 112, A.sub.1 to A.sub.12 may each
independently be selected from the group of CR.sub.1 to CR.sub.12
and N, provided that at least one of A.sub.7 to A.sub.12 is N.
R.sub.1 to R.sub.6 adjacent to each other can form a fused ring,
and R.sub.7 to R.sub.12 adjacent to each other can form a fused
ring.
[0076] X may be selected from the group of O, S, Se, and NR.sub.13.
Y may be CR.sub.14 or N, provided that when X is selected from the
group of O, S, and Se, Y is N,
[0077] L may be a substituted or unsubstituted C6 to C50
arylene,
[0078] a may be 0 or 1, provided that when a is 0, A.sub.1 to
A.sub.6 are each independently CR.sub.1 to CR.sub.6, and when a is
1, at least one of A.sub.1 to A.sub.6 is N,
[0079] b and c may each independently be an integer of 1 to 3,
and
[0080] R.sub.1 to R.sub.14 may each independently be selected from
the group of hydrogen, a halogen, a nitrile, a cyano, a nitro, an
amide, a carbonyl, an ester, a substituted or unsubstituted alkyl,
a substituted or unsubstituted alkylene, a substituted or
unsubstituted alkoxy, a substituted or unsubstituted alkenyl, a
substituted or unsubstituted alkenylene, a substituted or
unsubstituted alkynyl, a substituted or unsubstituted alkynylene, a
substituted or unsubstituted cycloalkyl, a substituted or
unsubstituted cycloalkylene, a substituted or unsubstituted aryl, a
substituted or unsubstituted arylene, a substituted or
unsubstituted arylamine, a substituted or unsubstituted
heteroarylamine, a substituted or unsubstituted heterocycle, a
substituted or unsubstituted amino, BRR', or SiRR'R'', wherein R,
R' and R'' are each independently a substituted or unsubstituted
alkyl or a substituted or unsubstituted aryl.
[0081] When an adjacent two of R.sub.1 to R.sub.6 form a fused
ring, or an adjacent two of R.sub.7 to R.sub.12 form a fused ring,
a fused ring including A.sub.1 to A.sub.6 and a fused ring
including A.sub.7 to A.sub.12 may be polycyclic aryls, e.g.,
naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryenyl, pyrenyl,
fluorenyl, and the like. For example, when at least one of A.sub.7
to A.sub.12 is N, one or more carbons of the polycyclic aryls may
be substituted with N.
[0082] When R.sub.7 to R.sub.12 are each independently substituted
or unsubstituted aryl or substituted or unsubstituted arylene, the
compound may be usefully applicable to an emission layer.
[0083] When X is selected from the group of O, S, and Se, Y may be
N, such that at least one of X and Y is N. In this case, the LUMO
(lowest unoccupied molecular orbital) energy level may be lowered
and electron affinity of a molecule may be increased, thereby
improving injection and transport characteristics of electrons.
Accordingly, voltage required for driving an organic light emitting
diode may be decreased and electrical power efficiency may be
improved.
[0084] The functional substituents including X and Y may provide
the compound with a predetermined rigidity and thus may increase
intermolecular interaction. The compound for an organic
photoelectric device according to an embodiment may have thermal
stability due to a high glass transition temperature, and may
thereby improve life-span of an organic light emitting diode.
[0085] L may be a substituted or unsubstituted C6 to C50 arylene.
For example, aryls of R.sub.7 to R.sub.12 and L is a C6 to C50
aryl, and the aryl may be monocyclic aryls such as phenyl; or
polycyclic aryls such as naphthyl, anthracenyl, phenanthrenyl,
pyrenyl, peryenyl, and so on. The compound may be useful for a
material of an emission layer.
[0086] The linking group L may increase intermolecular interaction,
and may thereby improve thermal stability. In addition, L may
adjust the .pi.-conjugation length and also light emitting in a
visual region. Accordingly, a compound for an organic photoelectric
device according to an embodiment may be usefully applied to an
emission layer.
[0087] b and c may be integers of 1 to 3. When b and c are 2 or
more, each repeating unit may be different.
[0088] For example, when c is 2, two repeating units may be linked
to each other at a meta position of the benzene ring including
A.sub.1 to A.sub.6.
[0089] In another implementation, the compound for an organic
photoelectric device according to an embodiment may include a
compound represented by the following Chemical Formula 113:
##STR00038##
[0090] In Chemical Formula 113,
[0091] A.sub.2, A.sub.4 to A.sub.12 and A.sub.7' to A.sub.12' may
each independently be selected from the group of CR.sub.2, CR.sub.4
to CR.sub.12, CR.sub.7' to CR.sub.12', and N, provided at least one
of A.sub.7 to A.sub.12 is N, and at least one of A.sub.7' to
A.sub.12' is N. R.sub.4 to R.sub.6 adjacent to each other can form
a fused ring, R.sub.7 to R.sub.12 adjacent to each other can form a
fused ring, and R.sub.7' to R.sub.12' adjacent to each other can
form a fused ring,
[0092] X may be selected from the group of O, S, Se, and NR.sub.13.
Y may be CR.sub.14 or N, provided that when X is selected from the
group of O, S, and Se, Y is N,
[0093] L and L' may each independently be a substituted or
unsubstituted C6 to C50 arylene,
[0094] a and a' may each independently be 0 or 1, provided that
when a and a' are each independently 0, A.sub.2, A.sub.4 to A.sub.6
are each independently CR.sub.2, and CR.sub.4 to CR.sub.6, and when
a and a' are each independently 1, at least one of A.sub.2, and
A.sub.4 to A.sub.6 is N,
[0095] b and b' may each independently be an integer ranging from 1
to 3, and
[0096] R.sub.2, R.sub.4 to R.sub.14, and R.sub.7' to R.sub.12' may
each independently be hydrogen, a halogen, a nitrile, a cyano, a
nitro, an amide, a carbonyl, an ester, a substituted or
unsubstituted alkyl, a substituted or unsubstituted alkylene, a
substituted or unsubstituted alkoxy, a substituted or unsubstituted
alkenyl, a substituted or unsubstituted alkenylene, a substituted
or unsubstituted alkynyl, a substituted or unsubstituted
alkynylene, a substituted or unsubstituted cycloalkyl, a
substituted or unsubstituted cycloalkylene, a substituted or
unsubstituted aryl, a substituted or unsubstituted arylene, a
substituted or unsubstituted arylamine, a substituted or
unsubstituted hetero arylamine, a substituted or unsubstituted
heterocycle, a substituted or unsubstituted amino, BRR', or
SiRR'R'', wehrein R, R', and R'' may each independently be a
substituted or unsubstituted alkyl, or a substituted or
unsubstituted aryl.
[0097] An adjacent two of R.sub.4 to R.sub.6 can form a fused ring,
an adjacent two of R.sub.7 to R.sub.12 can form a fused ring, and
an adjacent two of R.sub.7' to R.sub.12' can form a fused ring. The
fused ring may be polycyclic aryls such as naphthyl, anthracenyl,
phenanthrenyl, pyrenyl, peryenyl, pyrenyl, fluorenyl, and the like.
For example, when at least one of A.sub.7 to A.sub.12 is N, and at
least one of A.sub.7' to A.sub.12' is N, one or more carbons of the
polycyclic aryls may be substituted with N.
[0098] L and L' may each independently be a substituted or
unsubstituted C6 to C50 arylene. For example, the aryl may be a C6
to C50 aryl, and the aryl may be monocyclic aryls such as phenyl;
or polycyclic aryls such as naphthyl, anthracenyl, phenanthrenyl,
pyrenyl, peryenyl, and so on. The compound may be useful for a
material of an emission layer.
[0099] b and b' may each independently integers of 1 to 3, and when
b and b' are 2 or more, each repeating unit may be different.
[0100] When R.sub.1 to R.sub.14 in Chemical Formula 112 and
R.sub.2, R.sub.4 to R.sub.14, and R.sub.7' to R.sub.12' in Chemical
Formula 113 are a substituted or unsubstituted aryl, a substituted
or unsubstituted arylene, or a substituted or unsubstituted
arylamine, the aryl may be a C6 to C50 aryl. For example, when the
aryls are monocyclic aryls such as phenyl, biphenyl, terphenyl,
styrene, and so on, or polycyclic aryls such as naphthyl,
anthracenyl, phenanthrenyl, pyrenyl, peryenyl, and so on, the
compound may be useful for a material of an emission layer.
[0101] When R.sub.1 to R.sub.14 in Chemical Formula 112 and
R.sub.2, R.sub.4 to R.sub.14, and R.sub.7' to R.sub.12' in Chemical
Formula 113 are a substituted or unsubstituted heteroarylamine, or
a substituted or unsubstituted heteroaryl, the aryl may be the same
as described above. The heteroaryl may refer to an aryl including 1
to 3 heteroatoms of N, O, S, or P, and remaining carbons.
[0102] R.sub.1 to R.sub.14 in Chemical Formula 112 and R.sub.2,
R.sub.4 to R.sub.14, and R.sub.7' to R.sub.12' in Chemical Formula
113 may be a substituted or unsubstituted arylamine, and the
arylamine may be selected from the group of diphenyl amine,
dinaphthyl amine, dibiphenyl amine, phenyl naphthyl amine, phenyl
diphenyl amine, ditolyl amine, phenyl tolyl amine, carbazolyl, and
triphenyl amine, which provides balance between electron and hole
mobility characteristics.
[0103] When R.sub.1 to R.sub.14 in Chemical Formula 112 and
R.sub.2, R.sub.4 to R.sub.14, and R.sub.7' to R.sub.12' in Chemical
Formula 113 are a substituted or unsubstituted heterocycle, the
heterocycle may be selected from the group of thiophenyl, furanyl,
pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl,
pyridinyl, pyridazinyl, quinolinyl, isoquinolinine, acridyl,
imidazopyridinyl, and imidazopyrimidinyl.
[0104] For example, a substituent linked to nitrogen (N) of the
imidazolyl or triazolyl may be selected from the group of a
substituted or unsubstituted alkyl such as a substituted or
unsubstituted methyl, a substituted or unsubstituted ethyl, a
substituted or unsubstituted propyl, a substituted or unsubstituted
isopropyl, a substituted or unsubstituted butyl, a substituted or
unsubstituted t-butyl, a substituted or unsubstituted pentyl, a
substituted or unsubstituted hexyl, and a substituted or
unsubstituted heptyl; a substituted or unsubstituted cycloalkyl
such as a substituted or unsubstituted cyclopentyl, a substituted
or unsubstituted cyclohexyl, and so on; a substituted or
unsubstituted aryl such as a substituted or unsubstituted phenyl, a
substituted or unsubstituted biphenyl, a substituted or
unsubstituted naphthyl, and so on; and a substituted or
unsubstituted heterocycle. The heterocycle is preferably a
heteroaryl such as pyridyl, bipyridyl, quinolyl, isoquinolyl, and
so on.
[0105] At least one of R.sub.1 to R.sub.12 in Chemical Formula 112
and at least one of R.sub.2, R.sub.4 to R.sub.12, and R.sub.7' to
R.sub.12' in Chemical Formula 113 may be substituted with at least
one of substituent selected from an amine-substituted alkyl, an
amine-substituted cycloalkyl, an amine-substituted aryl, and an
amine-substituted heterocycle, which makes the compound be
applicable to a hole injection layer (HIL) or a hole transport
layer (HTL).
[0106] At least one of R.sub.1 to R.sub.12 in Chemical Formula 112
and at least one of R.sub.2, R.sub.4 to R.sub.12, R.sub.7' to
R.sub.12' in Chemical Formula 113 may be substituted with a
substituent selected from the group consisting of a nitrile, a
nitro, an amide, a carbonyl, and a substituted or unsubstituted
heterocycle, which reinforces an electron injection or transport
capability and thereby makes the compound be applicable to an
electron injection layer (EIL) or an electron transport layer
(ETL). Accordingly, hole transport and electron transport
capabilities may be simultaneously improved.
[0107] The various substituents of the above-described compound
represented by the above Chemical Formulae 112 and 113 may not
change principal properties of the compound for an organic
photoelectric device according to one embodiment.
[0108] Examples of the compounds for an organic photoelectric
device according to an embodiment may include compounds represented
by the following Chemical Formulae 114 to 183, but are not limited
thereto.
##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##
[0109] The compound for an organic photoelectric device including
one of the above compounds may play a role of hole injection, hole
transport, light emitting, or electron injection and/or transport,
and also as a light emitting host with an appropriate dopant. The
compound for an organic photoelectric device may improve thermal
stability and may decrease a driving voltage, thereby improving
life-span and efficiency characteristics of an organic
photoelectric device when included in an organic thin layer.
[0110] The compound for an organic photoelectric device including
the above compound may play a role of hole and electron transport,
and also as a light emitting host with an appropriate dopant. For
example, the dopant may be a reducing dopant. The reducing dopant
may be selected from the group of an alkaline metal, an alkaline
earth metal, a rare earth element metal, an oxide of an alkaline
metal, a halide of an alkaline metal, an organic complex of an
alkaline metal, an oxide of an alkaline earth metal, a halide of an
alkaline earth metal, an organic complex of an alkaline earth
metal, an oxide of an alkaline earth metal, a halide of an alkaline
earth metal, an organic complex of an alkaline earth metal, an
oxide of a rare earth element metal, a halide of a rare earth
element metal, and an organic complex of a rare earth element
metal.
[0111] The compound for an organic photoelectric device may be
usefully used for a host material or a charge transfer material. In
an implementation, the organic photoelectric device may include an
organic light emitting diode, an organic solar cell, an organic
transistor, an organic memory device, and the like.
[0112] As for an organic solar cell, the compound of an embodiment
may be included in an electrode or an electrode buffer layer and
may thereby improve quantum efficiency. As for an organic
transistor, the compound can be used as an electrode material in a
gate, a source-drain electrode, and the like.
[0113] Hereinafter, an organic light emitting diode is illustrated
in more detail. An organic photoelectric device according to an
embodiment may include the compound for an organic photoelectric
device in at least one layer among organic thin layers, when an
organic photoelectric device in general includes an anode, a
cathode, and at least one organic thin layer disposed between the
anode and cathode.
[0114] An organic light emitting diode may include a compound
having various energy band gaps, and may thereby satisfy various
conditions desirable for a hole injection layer (HIL), a hole
transport layer (HTL), an emission layer, an electron injection
layer (EIL), an electron transport layer (ETL), and the like.
Accordingly, the organic light emitting diode may realize a low
driving voltage and high luminous efficiency.
[0115] The organic thin layer may include one selected from the
group of an emission layer, an electron transport layer (ETL), an
electron injection layer (EIL), a hole transport layer (HTL), a
hole injection layer (HIL), and a hole blocking layer. At least one
layer may include the compound for an organic photoelectric device
according to an embodiment.
[0116] FIGS. 1 to 5 illustrate cross-sectional views showing
organic photoelectric devices including the organic compounds
according to various embodiments.
[0117] Referring to FIGS. 1 to 5, the organic photoelectric devices
100, 200, 300, 400, and 500 according to an embodiment may include
at least one organic thin layer 105 interposed between an anode 120
and a cathode 110.
[0118] The anode 120 may include an anode material laving a large
work function to help hole injection into an organic thin layer.
The anode material may include a metal such as nickel, platinum,
vanadium, chromium, copper, zinc, and gold, or alloys thereof; a
metal oxide such as zinc oxide, indium oxide, indium tin oxide
(ITO), and indium zinc oxide (IZO); a combined metal and oxide such
as ZnO:Al or SnO.sub.2:Sb; or a conductive polymer such as
poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene]
(PEDT), polypyrrole, and polyaniline, but is not limited
thereto.
[0119] The cathode 110 may include a cathode material having a
small work function to help electron injection into an organic thin
layer. The cathode material may include a metal such as magnesium,
calcium, sodium, potassium, titanium, indium, yttrium, lithium,
gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or
a multi-layered material such as LiF/Al, Liq/Al, LiO.sub.2/Al,
LiF/Ca, LiF/Al, and BaF.sub.2/Ca, but is not limited thereto.
[0120] Referring to FIG. 1, the organic photoelectric device 100
may include an organic thin layer 105 including only an emission
layer 130.
[0121] Referring to FIG. 2, a double-layered organic photoelectric
device 200 may include an organic thin layer 105 including an
emission layer 230 including an electron transport layer (ETL), and
a hole transport layer (HTL) 140. The emission layer 130 also
functions as an electron transport layer (ETL), and the hole
transport layer (HTL) 140 layer has an excellent binding property
with a transparent electrode such as ITO or an excellent hole
transporting property.
[0122] Referring to FIG. 3, a three-layered organic photoelectric
device 300 may include an organic thin layer 105 including an
electron transport layer (ETL) 150, an emission layer 130, and a
hole transport layer (HTL) 140. The emission layer 130 is
independently installed, and layers having an excellent electron
transporting property or an excellent hole transporting property
are separately stacked.
[0123] As shown in FIG. 4, a four-layered organic photoelectric
device 400 may include an organic thin layer 105 including an
electron injection layer (EIL) 160, an emission layer 130, a hole
transport layer (HTL) 140, and a hole injection layer (HIL) 170 for
binding with the anode 120 of, e.g., ITO.
[0124] As shown in FIG. 5, a five layered organic photoelectric
device 500 may include an organic thin layer 105 including an
electron transport layer (ETL) 150, an emission layer 130, a hole
transport layer (HTL) 140, and a hole injection layer (HIL) 170,
and further includes an electron injection layer (EIL) 160 to
achieve a low voltage.
[0125] The light emitting diode may be fabricated by forming an
anode on a substrate, forming an organic thin layer, and forming a
cathode thereon. The organic thin layer may be formed by a dry
coating method such as evaporation, sputtering, plasma plating, and
ion plating, or a wet coating method such as spin coating, dipping,
and flow coating.
[0126] Another embodiment provides a display device including the
organic photoelectric device according to the above-described
embodiment.
[0127] The following Examples and Comparative Examples are provided
in order to set forth particular details of one or more
embodiments. However, it will be understood that the embodiments
are not limited to the particular details described. Further, the
Comparative Examples are set forth to highlight certain
characteristics of certain embodiments, and are not to be construed
as either limiting the scope of the invention as exemplified in the
Examples or as necessarily being outside the scope of the invention
in every respect.
Synthesis Example 1
Synthesis of
2-(3-(anthracen-9-yl)-5-bromophenyl)benzo[d]oxazole
##STR00064##
[0129] 10 g (27.7 mmol) of 3-(anthracen-9-yl)-5-bromobenzaldehyde
and 3.6 g (33.2 mmol) of 2-aminophenol were dissolved in 100 ml of
acetic acid, and then agitated at room temperature for 30 minutes.
Next, 14.7 g (33.2 mmol) of lead (IV) acetate was added thereto.
The resulting mixture was agitated at 50.degree. C. for 1 hour.
Then, water was poured therein. The resulting product was treated
with ethyl acetate to perform extraction, and then the solvent was
removed under a reduced pressure. The extract was separated through
a column and dried, obtaining 4.5 g (Y=33%) of a white solid.
Synthesis Example 2
Synthesis of
2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-phenyl-1,3,4--
oxadiazole
##STR00065##
[0131] 5 g (16.6 mmol) of
2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole, 5.1 g (19.9 mmol) of
bis(pinacolato)diboron, 0.41 g (3 mol %) of a complex of
[1,1'-bis(diphenylphosphino)ferrocene]dichloro-palladium (II) with
dichloromethane, and 4.9 g (49.8 mmol) of potassium acetate were
dissolved in 100 ml of dimethylformaimde (DMF). The solution was
reacted at 80.degree. C. for 12 hours. The reactant was extracted
with ethyl acetate. The extract was treated under a reduced
pressure to remove the solvent and separated through a column,
obtaining 3.1 g (Y=53%) of a light yellow solid.
Synthesis Example 3
Synthesis of
2-(3,5-dibromophenyl)-1-phenyl-1H-benzo[d]imidazole
##STR00066##
[0133] 20 g (75.8 mmol) of 3,5-dibromobenzaldehyde and 16.8 g (90.9
mmol) of N-phenyl-o-phenylenediamine were dissolved in 150 mL of
acetic acid. The solution was agitated at room temperature for 30
minutes. Next, 37 g (83.4 mmol) of lead(IV) acetate was added
thereto. The resulting product was agitated at 50.degree. C. for 1
hour. Then, water was poured into the obtained reactant. The
resulting product was treated with ethyl acetate to perform
extraction and the solvent was removed under a reduced pressure.
The extract was separated through a column and dried, obtaining 9.5
g (Y=29%) of a yellow solid.
Synthesis Example 4
Synthesis of
2-(3-bromo-5-(pyridin-3-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole
##STR00067##
[0135] 9.4 g (22.0 mmol) of
2-(3,5-dibromophenyl)-1-phenyl-1H-benzo[d]imidazole according to
Synthesis Example 3, 2.7 g (22.0 mmol) of pyridine-3-boronic acid,
0.76 g (3 mol %) of tetrakis(triphenylphosphine)palladium (0), and
6.1 g (44.0 mmol) of potassium carbonate were dissolved in 300 ml
of tetrahydrofuran/H.sub.2O mixed in a volume ratio of 2/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent therein. The reactant was
separated through a column and dried, obtaining 5.15 g (Y=54%) of a
yellow solid.
Synthesis Example 5
Synthesis of 2-(3,5-dibromophenyl)benzo[d]thiazole
##STR00068##
[0137] 5.03 g (19.1 mmol) of 3,5-dibromobenzaldehyde and 3.1 mL
(28.6 mmol) of 2-aminothiophenol were dissolved in 60 mL of acetic
acid. The solution was agitated at room temperature for 30 minutes.
9.78 g (21.0 mmol) of lead(IV) acetate was added thereto. The
resulting mixture was agitated at 50.degree. C. for 1 hour. Then,
water was poured into the reactant. It was extracted with ethyl
acetate. The extract was separated through a column and dried,
obtaining 4.74 g (Y=67%) of a white solid.
Synthesis Example 6
Synthesis of 2-(3-bromo-5-(pyridin-3-yl)phenyl)benzo[d]thiazole
##STR00069##
[0139] 4.74 g (12.8 mmol) of 2-(3,5-dibromophenyl)benzo[d]thiazole)
according to Synthesis Example 5, 1.89 g (15.4 mmol) of
pyridine-3-boronic acid, 0.44 g (3 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 5.31 g (38.4 mmol)
of potassium carbonate were dissolved in 50 ml of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 4/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 2.54 g (Y=54%) of a white
solid.
Synthesis Example 7
Synthesis of 3-(2H-tetrazol-5-yl)pyridine
##STR00070##
[0141] 30 g (288 mmol) of 3-pyridinecarbonitrile, 28.1 g (432 mmol)
of sodium azide (NaN.sub.3), and 23.1 g (432 mmol) of ammonium
chloride were dissolved in 200 mL of DMF. The solution was reacted
at 100.degree. C. for 24 hours. Then, water was added to the
obtained reactant. The resulting product was neutralized with
hydrochloric acid and then filtered, obtaining 19.6 g (Y=46%) of a
white solid.
Synthesis Example 8
Synthesis of 3-(5-(3-bromophenyl)-1,3,4-oxadiazol-2-yl)pyridine
##STR00071##
[0143] 16.8 g (114 mmol) of 3-(2H-tetrazol-5-yl)pyridine) according
to Synthesis Example 7 and 25 g (114 mmol) of
3-bromobenzoylchloride were dissolved in 180 mL of o-xylene. The
solution was reacted at 150.degree. C. for 8 hours. The obtained
reactant was purified under a reduced pressure and washed with
methanol, obtaining 30 g (Y=87%) of a white solid.
Synthesis Example 9
Synthesis of
3-(5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadia-
zol-2-yl)pyridine
##STR00072##
[0145] 12 g (40 mmol) of
3-(5-(3-bromophenyl)-1,3,4-oxadiazol-2-yl)pyridine according to
Synthesis Example 8, 12.2 g (48 mmol) of bis(pinacolato)diboron,
0.98 g (3 mol %) of a complex of
[1,1'-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) with
dichloromethane, 5.9 g (60 mmol) of potassium acetate were
dissolved in 250 ml of dimethylformaimde (DMF). The solution was
reacted at 80.degree. C. for 12 hours. The obtained reactant was
extracted with ethyl acetate and treated under a reduced pressure
to remove the solvent. The extract was separated through a column
and dried, obtaining 10 g (Y=71%) of a white solid.
Synthesis Example 10
Synthesis of 2-(2,5-dibromophenyl)benzo[d]thiazole
##STR00073##
[0147] 5 g (18.5 mmol) of 2,5-dibromobenzaldehyde, 3 mL (27.7 mmol)
of 2-aminothiophenol, and 2.35 g (9.25 mmol) of iodine were
dissolved in 100 mL of DMF. The solution was reacted at 100.degree.
C. for 1 hour. The obtained reactant was purified through a column,
obtaining 4.64 g (Y=68%) of a white solid.
Synthesis Example 11
Synthesis of 2-(2-bromopyridin-3-yl)benzo[d]thiazole
##STR00074##
[0149] 6.58 g (34.0 mmol) of 2-bromo-3-pyrdinecarboxaldehyde and
5.5 mL (50.9 mmol) of 2-aminothiophenol were dissolved in 150 mL of
acetic acid. The solution was agitated at room temperature for 30
minutes. Next, 19.0 g (40.8 mmol) of lead (IV) acetate was added
thereto. The resulting product was agitated at 50.degree. C. for 1
hour. Then, water was added to the obtained reactant. The mixture
was extracted with ethyl acetate and treated under a reduced
pressure to remove the solvent, obtaining 5.55 g (Y=55%) of a white
solid.
Synthesis Example 12
Synthesis of 2-(3,5-dibromophenyl)benzo[d]oxazole
##STR00075##
[0151] 10 g (37.9 mmol) of 3,5-dibromobenzaldehyde and 5 g (45.5
mmol) of 2-aminophenol were dissolved in 200 mL of acetic acid. The
solution was agitated at room temperature for 30 minutes. Next,
20.2 g (45.5 mmol) of lead(IV) acetate was added thereto. The
resulting product was agitated at 50.degree. C. for 1 hour. Then,
water was added to the obtained reactant. The mixture was extracted
with ethyl acetate and treated under a reduced pressure to remove
the solvent, obtaining 5.7 g (Y=42%) of a white solid.
Example 1
Synthesis of a Compound of Chemical Formula 44
##STR00076##
[0153] 5 g (18.1 mmol) of 3,5-di-(3-pyridinyl)-benzene boronic
acid), 8.16 g (18.1 mmol) of
2-(3-(anthracen-9-yl)-5-bromophenyl)benzo[d]oxazole according to
Synthesis Example 1, 0.63 g (3 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 5 g (36.2 mmol) of
potassium carbonate were dissolved in 450 ml of a solvent of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 2/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 6 g (Y=55%) of a white
solid.
Example 2
Synthesis of a Compound of Chemical Formula 64
##STR00077##
[0155] 2.32 g (6.7 mmol) of
(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-phenyl-1,3,4-
-oxadiazole according to Synthesis Example 2, 2.5 g (5.5 mmol) of
2-(3-(anthracen-9-yl)-5-bromophenyebenzo[d]oxazole according to
Synthesis Example 1, 0.19 g (3 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 1.2 g (11.1 mmol) of
sodium carbonate were dissolved in 90 ml of a solvent of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 2/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 2.6 g (Y=79%) of a white
solid.
Example 3
Synthesis of a Compound of Chemical Formula 83
##STR00078##
[0157] 4.14 g (15.0 mmol) of 3,5-di-(3-pyridinyl)-benzene boronic
acid, 6.4 g (15.0 mmol) of
2-(3-bromo-5-(pyridin-3-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole
according to Synthesis Example 4, 0.52 g (3 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 4.15 g (30.0 mmol)
of potassium carbonate were dissolved in 300 ml of a solvent of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 2/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 1.2 g (Y=13%) of a white
solid.
Example 4
Synthesis of a Compound of Chemical Formula 87
##STR00079##
[0159] 0.84 g (3.1 mmol) of 3,5-di-(3-pyridinyl)-benzene boronic
acid), 1.0 g (2.8 mmol) of
2-(3-bromo-5-(pyridin-3-yl)phenyl)benzo[d]thiazole according to
Synthesis Example 6, 0.14 g (5 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 1.15 g (8.34 mmol)
of potassium carbonate were dissolved in 25 mL of a solvent of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 4/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 1.35 g (Y=92%) of a white
solid.
Example 5
Synthesis of a Compound of Chemical Formula 92
##STR00080##
[0161] 4.63 g (13.3 mmol) of
3-(5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadia-
zol-2-yl)pyridine according to Synthesis Example 9, 5.15 g (12.1
mmol) of
2-(3-bromo-5-(pyridin-3-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole)
according to Synthesis Example 4, 0.47 g (3 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 3.3 g (24.2 mmol) of
potassium carbonate were dissolved in 300 mL of a solvent
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 4/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 2 g (Y=33%) of a white
solid.
Example 6
Synthesis of a Compound of Chemical Formula 96
##STR00081##
[0163] 1 g (2.76 mmol) of 2-(2,5-dibromophenyl)benzo[d]thiazole
according to Synthesis Example 10, 0.85 g (6.9 mmol) of
pyridine-3-boronic acid, 0.28 g (10 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 2.3 g (16.6 mmol) of
potassium carbonate were dissolved in 25 mL of a solvent of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 4/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 0.8 g (Y=79%) of a white
solid.
Example 7
Synthesis of a Compound of Chemical Formula 105
##STR00082##
[0165] 1.33 g (4.8 mmol) of 3,5-di-(3-pyridinyl)-benzene boronic
acid, 1.7 g (5.8 mmol) of 2-(2-bromopyridine-3-yl)benzo[d]thiazole
according to Synthesis Example 11, 0.28 g (5 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 2.0 g (14.4 mmol) of
potassium carbonate were dissolved in 30 mL of a solvent of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 4/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 2.28 g (Y=88%) of a white
solid.
Example 8
Synthesis of a Compound of Chemical Formula 108
##STR00083##
[0167] 2.3 g (8.4 mmol) of 3,5-di-(3-pyridinyl)-benzene boronic
acid, 1.5 g (4.0 mmol) of 2-(3,5-dibromophenyl)benzo[d]thiazole
according to Synthesis Example 5, 0.46 g (10 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 3.3 g (23.9 mmol) of
potassium carbonate were dissolved in 50 mL of a solvent of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 4/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 2.04 g (Y=75%) of a white
solid.
Example 9
Synthesis of a Compound of Chemical Formula 110
##STR00084##
[0169] 4.3 g (15.6 mmol) of 3,5-di-(3-pyridinyl)-benzene boronic
acid, 2.5 g (7.1 mmol) of 2-(3,5-dibromophenyl)benzo[d]oxazole
according to Synthesis Example 12, 0.82 g (10 mol %) of
tetrakis(triphenylphosphine)palladium (0), and 5.9 g (42.7 mmol) of
potassium carbonate were dissolved in 100 mL of a solvent of
tetrahydrofuran/H.sub.2O mixed in a volume ratio of 4/1. The
solution was reacted at 80.degree. C. for 12 hours. The obtained
reactant was extracted with ethyl acetate and treated under a
reduced pressure to remove the solvent. The extract was separated
through a column and dried, obtaining 3.37 g (Y=72%) of a white
solid.
[0170] The compounds according to Examples 1 to 9 were analyzed
through .sup.1H NMR (nuclear magnetic resonance spectroscopy). The
results are respectively provided in FIGS. 6 to 14.
Comparative Example 1
2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD)
[0171] 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD),
which is conventionally known to have an excellent charge transport
capability, was prepared.
Example 10
Fabrication of an Organic Light Emitting Diode
[0172] A 15 .OMEGA./cm.sup.2 (120 nm) ITO glass substrate (Corning
Inc.) was prepared to have a size of 25 mm.times.25 mm.times.0.7
mm, and was respectively washed in isopropyl alcohol and pure water
for 5 minutes, and was then cleaned again with UV and ozone.
[0173] Next, a 40 nm-thick
N,N'-di(4-(N,N'-diphenyl-amino)-phenyl)-N,N'-diphenylbenzidine
(DNTPD) hole injection layer (HIL) was formed on the substrate.
[0174] Then, N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidine
(NPB) was vacuum-deposited to form a 10 nm-thick hole transport
layer (HTL) on the hole injection layer (HIL).
[0175] EB-46 and EB-512 (e-Ray Optoelectronics Technology Co.,
Ltd.) as a light emitting material were vacuum-deposited in a
weight ratio of 94:6 to form a 40 nm-thick emission layer on the
hole transport layer (HTL).
[0176] The compound according to Example 2 as an electron transport
material was vacuum-deposited to form a 10 nm-thick electron
transport layer (ETL) on the emission layer.
[0177] On the electron transport layer (ETL), LiF 0.5 nm/Al 100 nm
were respectively and sequentially vacuum-deposited to form a
cathode including LiF/Al, fabricating an organic light emitting
diode of Example 10.
Example 11
Fabrication of an Organic Light Emitting Diode
[0178] An organic light emitting diode was fabricated according to
the same method as in Example 10, except for using a compound
according to Example 3 to form an electron transport layer
(ETL).
Example 12
Fabrication of an Organic Light Emitting Diode
[0179] An organic light emitting diode was fabricated according to
the same method as in Example 10, except for using a compound
according to Example 4 to form an electron transport layer
(ETL).
Example 13
Fabrication of an Organic Light Emitting Diode
[0180] An organic light emitting diode was fabricated according to
the same method as in Example 10, except for using a compound
according to Example 5 to form an electron transport layer
(ETL).
Example 14
Fabrication of an Organic Light Emitting Diode
[0181] An organic light emitting diode was fabricated according to
the same method as in Example 10, except for using a compound
according to Example 7 to form an electron transport layer
(ETL).
Example 15
Fabrication of an Organic Light Emitting Diode
[0182] An organic light emitting diode was fabricated according to
the same method as in Example 10, except for using a compound
according to Example 8 to form an electron transport layer
(ETL).
Example 16
Fabrication of an Organic Light Emitting Diode
[0183] An organic light emitting diode was fabricated according to
the same method as in Example 10, except for using a compound
according to Example 9 to form an electron transport layer
(ETL).
Comparative Example 2
Fabrication of an Organic Light Emitting Diode
[0184] An organic light emitting diode was fabricated according to
the same method as in Example 10, except for using an electron
transport material of Alq.sub.a to form an electron transport layer
(ETL).
[0185] Property Measurement and Analysis
[0186] 1) Driving Voltage, Luminance and Luminous Efficiency
[0187] The organic light emitting diodes of Examples 10 to 16 and
Comparative
[0188] Example 2 were measured regarding a driving voltage
(V.sub.d) required to produce luminance of 1000 nit, and current
efficiency (cd/A) and electrical power efficiency (lm/W) at the
same luminance. The results are shown in the following Table 1.
TABLE-US-00001 TABLE 1 At 1000 cd/m.sup.2 Max. Devices V.sub.d (V)
cd/A lm/W V.sub.on cd/A lm/W Comparative 7.40 4.68 1.99 3.60 4.72
2.88 Example 2 Example 10 6.20 5.19 2.63 3.20 5.35 3.25 Example 11
7.20 5.29 2.31 3.80 5.32 2.77 Example 12 6.40 5.00 2.45 3.00 5.32
3.34 Example 13 7.40 4.99 2.12 3.20 5.32 3.37 Example 14 6.40 5.80
2.85 3.00 5.88 3.51 Example 15 7.20 5.56 2.43 3.40 5.66 3.54
Example 16 6.00 6.04 3.16 3.20 6.32 4.14
[0189] Referring to Table 1 and FIGS. 15 and 16, the organic light
emitting diodes of Examples 10 to 16 generally had a sharply lower
driving voltage than those of Comparative Example 2. In addition,
referring to Table 1 and FIGS. 17 and 18, the organic light
emitting diodes of Examples 10 to 16 generally had a sharply lower
driving voltage but superbly high current efficiency and electrical
power efficiency.
[0190] These measurement results of the organic light emitting
diodes come from combination balance of holes and electrons in the
emission layer. The compounds of Examples 10 to 16 exhibited
excellent electron injection and transport characteristics compared
with Alq.sub.3, a general electron transport material.
[0191] 2) Thermal Stability
[0192] The compounds according to Examples 1 to 9 were analyzed in
a differential scanning calorimetry method (DSC), and then
secondarily analyzed in the same method. The analysis results of
the compounds according to Example 5 and Comparative Example 1 are
shown in FIGS. 19 and 20. Referring to FIGS. 19 and 20, the
compound of Example 5 had melting point peaks in the primary
analysis, but no melting point peak in the secondary analysis. On
the contrary, 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole
(PBD) according to Comparative Example 1 had a melting point peak
at 138.degree. C. in both primary and secondary analyses and a
crystallizing temperature at 65.degree. C. in the secondary
analysis. The compounds of Example 5 were identified to stably
exist in an amorphous state, compared with the conventional
material. Therefore, the organic light emitting diodes including
the compound of the embodiments exhibited reduced influence of
Joule heat generated during the operation, and thereby may have an
improved life-span characteristic compared with a conventional
organic light emitting diode.
[0193] By way of summation and review, both low molecular weight
organic light emitting and polymer organic light emitting diodes
have advantages of being self-light emitting and ultrathin, and
having a high speed response, a wide viewing angle, high image
quality, durability, a large driving temperature range, and the
like. For example, they have good visibility due to the self-light
emitting characteristic (compared with a conventional LCD (liquid
crystal display)) and have an advantage of decreasing thickness and
weight of LCD by up to a third (because they do not need a
backlight). In addition, since they have a response speed that is
1,000 times faster per microsecond unit than an LCD, they can
realize a perfect motion picture without an after-image. Based on
these advantages, they have been developed to have 80 times the
efficiency and more than 100 times the life-span since they were
first introduced. Recently, these diodes have been used in larger
displays, e.g., for a 40-inch organic light emitting diode
panel.
[0194] These large displays should simultaneously have improved
luminous efficiency and life-span. In order to increase the
luminous efficiency, smooth combination between holes and electrons
in an emission layer is desirable. However, an organic material may
generally have slower electron mobility than hole mobility and may
exhibit inefficient combination between holes and electrons.
[0195] In addition, devices may have a decreased life-span if the
material therein is crystallized due to Joule heat generated when
it is driven. 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole
(PBD) with a rapid transfer speed may have a good lifespan, but may
also lack thermal stability and may be crystallized when a device
is driven. In addition, BCP and an aluminum mixed coordination
complex (BAlq,
bis(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum) (which
is excellent in lowering hole mobility) have excellent
characteristic in lowering hole mobility but may deteriorate the
electron injection characteristic and may be crystallized when a
device is driven.
[0196] Accordingly, the embodiments provide a compound that
increases electron injection and mobility from a cathode and
simultaneously helps prevent movement of holes. The embodiments
also provide a compound having high thermal stability and that
suppresses crystallization when a device is driven.
[0197] The embodiments provide a compound that can act as a hole
injection, hole transport, light emitting, or electron injection
and/or transport material, and also as a light emitting host along
with an appropriate dopant.
[0198] The embodiments also provide an organic photoelectric device
including the compound for an organic photoelectric device, and
having decreased driving voltage and increased life-span and
efficiency.
[0199] The embodiments provide a compound for an organic
photoelectric device that is largely asymmetric. The asymmetric
structure may reinforce an amorphous characteristic and may thereby
suppress crystallization, thus improving thermal stability of the
compound for an organic photoelectric device. Accordingly, when an
organic photoelectric device is driven, the compound may decrease
the driving voltage and improve life-span and efficiency.
[0200] Example embodiments have been disclosed herein, and although
specific terms are employed, they are used and are to be
interpreted in a generic and descriptive sense only and not for
purpose of limitation. In some instances, as would be apparent to
one of ordinary skill in the art as of the filing of the present
application, features, characteristics, and/or elements described
in connection with a particular embodiment may be used singly or in
combination with features, characteristics, and/or elements
described in connection with other embodiments unless otherwise
specifically indicated. Accordingly, it will be understood by those
of skill in the art that various changes in form and details may be
made without departing from the spirit and scope of the present
invention as set forth in the following claims.
* * * * *