U.S. patent application number 14/902225 was filed with the patent office on 2016-05-05 for composition for organic optoelectronic device, organic optoelectronic device, and display device.
This patent application is currently assigned to SAMSUNG SDI CO., LTD.. The applicant listed for this patent is SAMSUNG SDI CO., LTD. Invention is credited to Pyeong-Seok CHO, Eui-Su KANG, Gi-Wook KANG, Hun KIM, Youn-Hwan KIM, Han-III LEE, Nam-Heon LEE, Jae-Jin OH, Yong-Tak YANG, Eun-Sun YU.
Application Number | 20160126472 14/902225 |
Document ID | / |
Family ID | 52628577 |
Filed Date | 2016-05-05 |
United States Patent
Application |
20160126472 |
Kind Code |
A1 |
OH; Jae-Jin ; et
al. |
May 5, 2016 |
COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC
OPTOELECTRONIC DEVICE, AND DISPLAY DEVICE
Abstract
Disclosed are a composition for an organic optoelectronic device
including at least one kind of a first host compound represented by
the Chemical Formula 1 and at least one kind of a second host
compound represented by the Chemical Formula 2, and an organic
optoelectronic device and a display device including the
composition.
Inventors: |
OH; Jae-Jin; (Suwon-si,
Gyeonggi-do, KR) ; KANG; Gi-Wook; (Suwon-si,
Gyeonggi-do, KR) ; KANG; Eui-Su; (Suwon-si,
Gyeonggi-do, KR) ; KIM; Youn-Hwan; (Suwon-si,
Gyeonggi-do, KR) ; KIM; Hun; (Suwon-si, Gyeonggi-do,
KR) ; YANG; Yong-Tak; (Suwon-si, Gyeonggi-do, KR)
; YU; Eun-Sun; (Suwon-si, Gyeonggi-do, KR) ; LEE;
Nam-Heon; (Suwon-si, Gyeonggi-do, KR) ; LEE;
Han-III; (Suwon-si, Gyeonggi-do, KR) ; CHO;
Pyeong-Seok; (Suwon-si, Gyeonggi-do, KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
SAMSUNG SDI CO., LTD |
Gyeonggi-do |
|
KR |
|
|
Assignee: |
SAMSUNG SDI CO., LTD.
Yongin-si, Gyeonggi
KR
|
Family ID: |
52628577 |
Appl. No.: |
14/902225 |
Filed: |
October 1, 2013 |
PCT Filed: |
October 1, 2013 |
PCT NO: |
PCT/KR2013/008790 |
371 Date: |
December 30, 2015 |
Current U.S.
Class: |
257/40 ;
252/500 |
Current CPC
Class: |
C07D 405/04 20130101;
H01L 51/0054 20130101; C09K 2211/1092 20130101; H01L 2251/5384
20130101; H01L 51/5012 20130101; C09K 2211/185 20130101; C07D
401/14 20130101; H01L 51/0072 20130101; C09K 2211/1044 20130101;
H01L 51/5016 20130101; C09K 11/06 20130101; C09K 2211/1059
20130101; H01L 51/0067 20130101; C09K 2211/1029 20130101; C09K
2211/1011 20130101; C07D 251/24 20130101; C09K 2211/1007 20130101;
C07D 401/04 20130101; C07D 405/14 20130101; C09K 2211/1088
20130101; C07D 409/04 20130101; C07D 409/14 20130101; C07D 209/86
20130101 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C09K 11/06 20060101 C09K011/06 |
Foreign Application Data
Date |
Code |
Application Number |
Sep 6, 2013 |
KR |
10-2013-0107391 |
Claims
1. A composition for an organic optoelectronic device, comprising
at least one kind of a first host compound represented by the
following Chemical Formula 1, and at least one kind of a second
host compound represented by the following Chemical Formula 2:
##STR00124## wherein, in the above Chemical Formula 1, Z is
independently N or CR.sup.a, at least one of Z is N, R.sup.1 to
R.sup.10 and R.sup.a are independently hydrogen, deuterium, a
substituted or unsubstituted C1 to C10 alkyl group, a substituted
or unsubstituted C6 to C12 aryl group, or a combination thereof, in
the above Chemical Formula 1, the total number of 6-membered rings
substituting the triphenylene group is less than or equal to 6, L
is a substituted or unsubstituted phenylene group, a substituted or
unsubstituted biphenylene group or a substituted or unsubstituted
terphenylene group, n1 to n3 are independently 0 or 1, and
n1+n2+n3.gtoreq.1, ##STR00125## wherein, in the above Chemical
Formula 2, Y.sup.1 is a single bond, a substituted or unsubstituted
C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20
alkenylene group, a substituted or unsubstituted C6 to C30 arylene
group, a substituted or unsubstituted C2 to C30 heteroarylene
group, or a combination thereof, Ar.sup.1 is a substituted or
unsubstituted C6 to C30 aryl group, a substituted or unsubstituted
C2 to C30 heteroaryl group, or a combination thereof, R.sup.11 to
R.sup.14 are independently hydrogen, deuterium, a substituted or
unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted
C6 to C50 aryl group, a substituted or unsubstituted C2 to C50
heteroaryl group, or a combination thereof, and at least one of
R.sup.11 to R.sup.14 and Ar.sup.1 comprises a substituted or
unsubstituted triphenylene group or a substituted or unsubstituted
carbazole group.
2. The composition for an organic optoelectronic device of claim 1,
wherein the first host compound is represented by the following
Chemical Formula 1-I or 1-II: ##STR00126## wherein, in the above
Chemical Formula 1-I and 1-II, Z is independently N or CR.sup.a, at
least one of Z is N, R.sup.1 to R.sup.10 and R.sup.a are
independently hydrogen, deuterium, a substituted or unsubstituted
C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12
aryl group, or a combination thereof, in the above Chemical Formula
1-I and 1-II, the total number of 6-membered rings substituting the
triphenylene group is less than or equal to 6, L is a substituted
or unsubstituted phenylene group, a substituted or unsubstituted
biphenylene group or a substituted or unsubstituted terphenylene
group, n1 to n3 are independently 0 or 1, and
n1+n2+n3.gtoreq.1.
3. The composition for an organic optoelectronic device of claim 1,
wherein L of the above Chemical Formula 1 is a single bond, a
substituted or unsubstituted phenylene group having a kink
structure, a substituted or unsubstituted biphenylene group having
a kink structure, or a substituted or unsubstituted terphenylene
group having a kink structure.
4. The composition for an organic optoelectronic device of claim 3,
wherein L of the above Chemical Formula 1 is selected from a single
bond or substituted or unsubstituted groups listed in the following
Group 1: ##STR00127## wherein, in the Group 1, R.sup.15 to R.sup.42
are independently hydrogen, deuterium, a substituted or
unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted
C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to
C30 heterocycloalkyl group, a substituted or unsubstituted C6 to
C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl
group, a substituted or unsubstituted amine group, a substituted or
unsubstituted C6 to C30 arylamine group, a substituted or
unsubstituted C6 to C30 heteroarylamine group, a substituted or
unsubstituted C1 to C30 alkoxy group, a halogen, a
halogen-containing group, a cyano group, a hydroxyl group, an amino
group, a nitro group, a carboxyl group, a ferrocenyl group, or a
combination thereof.
5. The composition for an organic optoelectronic device of claim 1,
wherein the first host compound has at least two kink
structures.
6. The composition for an organic optoelectronic device of claim 1,
wherein the first host compound is represented by the following
Chemical Formula 1a or 1b: ##STR00128## wherein, in the above
Chemical Formula 1a or 1b, Z is independently N or CR.sup.a, at
least one of Z is N, wherein in the above Chemical Formula 1a and
1b, the total number of 6-membered rings substituting the
triphenylene group is less than or equal to 6, and R.sup.1 to
R.sup.10 and R.sup.a are independently hydrogen, deuterium, a
substituted or unsubstituted C1 to C10 alkyl group, a substituted
or unsubstituted C6 to C12 aryl group, or a combination
thereof.
7. The composition for an organic optoelectronic device of claim 1,
wherein the first host compound is represented by one of the
following Chemical Formulae 1c to 1t: ##STR00129## ##STR00130##
##STR00131## ##STR00132## ##STR00133## ##STR00134## wherein, in the
above Chemical Formulae 1c to 1t, Z is independently N or CR.sup.a,
at least one of Z is N, wherein, in the above Chemical Formulae 1c
to 1t, the total number of 6-membered rings substituting the
triphenylene group is less than or equal to 6, R.sup.1 to R.sup.10
and R.sup.a are independently hydrogen, deuterium, a substituted or
unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted
C6 to C12 aryl group, or a combination thereof, and R.sup.60 to
R.sup.77 are independently hydrogen, deuterium, a substituted or
unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted
C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to
C30 heterocycloalkyl group, a substituted or unsubstituted C6 to
C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl
group, a substituted or unsubstituted amine group, a substituted or
unsubstituted C6 to C30 arylamine group, a substituted or
unsubstituted C6 to C30 heteroarylamine group, a substituted or
unsubstituted C1 to C30 alkoxy group, a halogen, a
halogen-containing group, a cyano group, a hydroxyl group, an amino
group, a nitro group, a carboxyl group, a ferrocenyl group, or a
combination thereof.
8. The composition for an organic optoelectronic device of claim 1,
wherein the first host compound is compounds listed in the
following Group 2: ##STR00135## ##STR00136## ##STR00137##
##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142##
##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147##
##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152##
##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157##
##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162##
##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167##
##STR00168## ##STR00169##
9. The composition for an organic optoelectronic device of claim 1,
wherein the second host compound is represented by at least one of
the following Chemical Formulae 2-I to 2-III: ##STR00170## wherein,
in the above Chemical Formulae 2-I to 2-III, Y.sup.1 to Y.sup.3 are
independently a single bond, a substituted or unsubstituted C1 to
C20 alkylene group, a substituted or unsubstituted C2 to C20
alkenylene group, a substituted or unsubstituted C6 to C30 arylene
group, a substituted or unsubstituted C2 to C30 heteroarylene
group, or a combination thereof, Ar.sup.1 and Ar.sup.2 are
independently a substituted or unsubstituted C6 to C30 aryl group,
a substituted or unsubstituted C2 to C30 heteroaryl group, or a
combination thereof, and R.sup.11 to R.sup.14 and R.sup.43 to
R.sup.54 are independently hydrogen, deuterium, a substituted or
unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted
C6 to C50 aryl group, a substituted or unsubstituted C2 to C50
heteroaryl group, or a combination thereof.
10. The composition for an organic optoelectronic device of claim
9, wherein Ar.sup.1 and Ar.sup.2 of the above Chemical Formula 2-I
are independently a substituted or unsubstituted phenyl group, a
substituted or unsubstituted biphenyl group, a substituted or
unsubstituted terphenyl group, a substituted or unsubstituted
naphthyl group, a substituted or unsubstituted anthracenyl group, a
substituted or unsubstituted carbazolyl group, a substituted or
unsubstituted benzofuranyl group, a substituted or unsubstituted
benzothiophenyl group, a substituted or unsubstituted fluorenyl
group, a substituted or unsubstituted pyridyl group, a substituted
or unsubstituted pyrimidinyl group, a substituted or unsubstituted
pyrazinyl group, a substituted or unsubstituted triazinyl group, a
substituted or unsubstituted triphenylene group, a substituted or
unsubstituted dibenzofuranyl group, a substituted or unsubstituted
dibenzothiopheneyl group, or combination thereof.
11. The composition for an organic optoelectronic device of claim
9, wherein the compound represented by the Chemical Formula 2-I is
selected from compounds listed in the following Group 5:
##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175##
##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180##
##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185##
##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190##
##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195##
##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200##
##STR00201## ##STR00202##
12. The composition for an organic optoelectronic device of claim
9, wherein the compound represented by the above Chemical Formula
2-II is selected from compounds listed in the following Group 6:
##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207##
##STR00208##
13. The composition for an organic optoelectronic device of claim
9, wherein the compound represented by the above Chemical Formula
2-III is selected from compounds listed in the following Group 7:
##STR00209## ##STR00210## ##STR00211## ##STR00212##
##STR00213##
14. The composition for an organic optoelectronic device of claim
1, wherein the first host compound and the second host compound are
included in a weight ratio of 1:10 to 10:1.
15. The composition for an organic optoelectronic device of claim
1, further comprising a phosphorescent dopant.
16. An organic optoelectronic device, comprising an anode and a
cathode facing each other, at least one organic layer interposed
between the anode and the cathode, wherein the organic layer
comprises the composition of claim 1.
17. The organic optoelectronic device of claim 16, wherein the
organic layer comprises an emission layer, and the emission layer
comprises the composition.
18. A display device comprising the organic optoelectronic device
of claim 16.
Description
TECHNICAL FIELD
[0001] A composition for an organic optoelectric device, an organic
optoelectric device and a display device using the same are
disclosed.
BACKGROUND ART
[0002] An organic optoelectric device is a device that converts
electrical energy into photoenergy, and vice versa.
[0003] An organic optoelectric device may be classified as follows
in accordance with its driving principles. One is an electronic
device where excitons generated by photoenergy are separated into
electrons and holes and the electrons and holes are transferred to
different electrodes respectively and electrical energy is
generated, and the other is a light emitting device to generate
photoenergy from electrical energy by supplying a voltage or a
current to electrodes.
[0004] Examples of the organic optoelectric device include an
organic photoelectric device, an organic light emitting diode, an
organic solar cell, and an organic photo-conductor drum, and the
like.
[0005] Among them, the organic light emitting diode (OLED) has
recently drawn attention due to an increase in demand for flat
panel displays. The organic light emitting diode converts
electrical energy into light by applying current to an organic
light emitting material, and has a structure in which an organic
layer is interposed between an anode and a cathode. Herein, the
organic layer may include an emission layer, and optionally an
auxiliary layer, and the auxiliary layer may include at least one
layer selected from, for example a hole injection layer, a hole
transport layer, an electron blocking layer, an electron transport
layer, an electron injection layer, and a hole blocking layer in
order to improve efficiency and stability of an organic light
emitting diode.
[0006] Performance of an organic light emitting diode may be
affected by characteristics of the organic layer, and among them,
may be mainly affected by characteristics of an organic material of
the organic layer.
[0007] Particularly, development for an organic material being
capable of increasing hole and electron mobility and simultaneously
increasing electrochemical stability is needed so that the organic
light emitting diode may be applied to a large-size flat panel
display.
DISCLOSURE
Technical Object
[0008] One embodiment provides a composition for an organic
optoelectric device capable of realizing an organic optoelectric
device having high efficiency, a long life-span, and the like.
[0009] Another embodiment provides an organic optoelectric device
including the composition.
[0010] Yet another embodiment provides a display device including
the organic optoelectric device.
Technical Solving Method
[0011] According to one embodiment, a composition for an organic
optoelectric device including at least one of a first host compound
represented by the following Chemical Formula 1 and at least one
kind of a second host compound represented by the following
Chemical Formula 2 is provided.
##STR00001##
[0012] In the above Chemical Formula 1,
[0013] Z is independently N or CR.sup.a,
[0014] at least one of Z is N,
[0015] R.sup.1 to R.sup.10 and R.sup.a are independently hydrogen,
deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a
substituted or unsubstituted C6 to C12 aryl group, or a combination
thereof,
[0016] in the above Chemical Formula 1, the total number of
6-membered rings substituting the triphenylene group is less than
or equal to 6,
[0017] L is a substituted or unsubstituted phenylene group, a
substituted or unsubstituted biphenylene group or a substituted or
unsubstituted terphenylene group,
[0018] n1 to n3 are independently 0 or 1, and
n1+n2+n3.gtoreq.1.
##STR00002##
[0019] In the above Chemical Formula 2,
[0020] Y.sup.1 is a single bond, a substituted or unsubstituted C1
to C20 alkylene group, a substituted or unsubstituted C2 to C20
alkenylene group, a substituted or unsubstituted C6 to C30 arylene
group, a substituted or unsubstituted C2 to C30 heteroarylene
group, or a combination thereof,
[0021] Ar.sup.1 is a substituted or unsubstituted C6 to C30 aryl
group, a substituted or unsubstituted C2 to C30 heteroaryl group,
or a combination thereof,
[0022] R.sup.11 to R.sup.14 are independently hydrogen, deuterium,
a substituted or unsubstituted C1 to C20 alkyl group, a substituted
or unsubstituted C6 to C50 aryl group, a substituted or
unsubstituted C2 to C50 heteroaryl group, or a combination thereof,
and
[0023] at least one of R.sup.11 to R.sup.14 and Ar.sup.1 includes a
substituted or unsubstituted triphenylene group or a substituted or
unsubstituted carbazole group.
[0024] According to another embodiment, an organic optoelectric
device includes an anode and a cathode facing each other, and at
least one organic layer interposed between the anode and the
cathode, wherein the organic layer includes the composition.
[0025] According to yet another embodiment, a display device
including the organic optoelectric device is provided.
Advantageous Effect
[0026] An organic optoelectric device having high efficiency and
long life-span may be realized.
DESCRIPTION OF DRAWINGS
[0027] FIGS. 1 and 2 are cross-sectional views of each organic
light emitting diode according to one embodiment.
BEST MODE
[0028] Hereinafter, embodiments of the present invention are
described in detail. However, these embodiments are exemplary, and
this disclosure is not limited thereto.
[0029] As used herein, when a definition is not otherwise provided,
the term "substituted" refers to one substituted with a deuterium,
a halogen, a hydroxy group, an amino group, a substituted or
unsubstituted C1 to C30 amine group, a nitro group, a substituted
or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a
C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C3 to
C30 heterocycloalkyl group, a C6 to C30 aryl group, a C6 to C30
heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to
C10 trifluoroalkyl group such as a trifluoromethyl group, and the
like, or a cyano group, instead of at least one hydrogen of a
substituent or a compound.
[0030] In addition, two adjacent substituents of the substituted
halogen, hydroxy group, amino group, substituted or unsubstituted
C1 to C20 amine group, a nitro group, substituted or unsubstituted
C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl
group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl
group, C6 to C30 aryl group, C6 to C30 heteroaryl group, C1 to C20
alkoxy group, fluoro group, C1 to C10 trifluoroalkyl group such as
trifluoromethyl group and the like, or cyano group may be fused
with each other to form a ring. For example, the substituted C6 to
C30 aryl group may be fused with another adjacent substituted C6 to
C30 aryl group to form a substituted or unsubstituted fluorene
ring.
[0031] In the present specification, when specific definition is
not otherwise provided, the term "hetero" refers to one including 1
to 3 hetero atoms selected from N, O, S, P, and Si, and remaining
carbons in one compound or substituent.
[0032] As used herein, when a definition is not otherwise provided,
the term "alkyl group" may refer to an aliphatic hydrocarbon group.
The alkyl group may refer to "a saturated alkyl group" without any
double bond or triple bond.
[0033] The alkyl group may be a C1 to C30 alkyl group. More
specifically, the alkyl group may be a C1 to C20 alkyl group or a
C1 to C10 alkyl group. For example, a C1 to C4 alkyl group includes
1 to 4 carbons in alkyl chain, and may be selected from methyl,
ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and
t-butyl.
[0034] Specific examples of the alkyl group may be a methyl group,
an ethyl group, a propyl group, an isopropyl group, a butyl group,
an isobutyl group, a t-butyl group, a pentyl group, a hexyl group,
a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a
cyclohexyl group, and the like.
[0035] As used herein, the term "aryl group" refers to a
substituent including all element of the cycle having p-orbitals
which form conjugation, and may be monocyclic, polycyclic or fused
ring polycyclic (i.e., rings sharing adjacent pairs of carbon
atoms) functional group.
[0036] As used herein, the term "heteroaryl group" may refer to
aryl group including 1 to 3 hetero atoms selected from N, O, S, P,
and Si and remaining carbons in one functional group. The
heteroaryl group may be a fused ring where each ring may include
the 1 to 3 heteroatoms.
[0037] More specifically, the substituted or unsubstituted C6 to
C30 aryl group and/or the substituted or unsubstituted C2 to C30
heteroaryl group may be a substituted or unsubstituted phenyl
group, a substituted or unsubstituted naphthyl group, a substituted
or unsubstituted anthracenyl group, a substituted or unsubstituted
phenanthryl group, a substituted or unsubstituted naphthacenyl
group, a substituted or unsubstituted pyrenyl group, a substituted
or unsubstituted biphenyl group, a substituted or unsubstituted
p-terphenyl group, a substituted or unsubstituted m-terphenyl
group, a substituted or unsubstituted chrysenyl group, a
substituted or unsubstituted triphenylenyl group, a substituted or
unsubstituted perylenyl group, a substituted or unsubstituted
indenyl group, a substituted or unsubstituted furanyl group, a
substituted or unsubstituted thiophenyl group, a substituted or
unsubstituted pyrrolyl group, a substituted or unsubstituted
pyrazolyl group, a substituted or unsubstituted imidazolyl group, a
substituted or unsubstituted triazolyl group, a substituted or
unsubstituted oxazolyl group, a substituted or unsubstituted
thiazolyl group, a substituted or unsubstituted oxadiazolyl group,
a substituted or unsubstituted thiadiazolyl group, a substituted or
unsubstituted pyridyl group, a substituted or unsubstituted
pyrimidinyl group, a substituted or unsubstituted pyrazinyl group,
a substituted or unsubstituted triazinyl group, a substituted or
unsubstituted benzofuranyl group, a substituted or unsubstituted
benzothiophenyl group, a substituted or unsubstituted
benzimidazolyl group, a substituted or unsubstituted indolyl group,
a substituted or unsubstituted quinolinyl group, a substituted or
unsubstituted isoquinolinyl group, a substituted or unsubstituted
quinazolinyl group, a substituted or unsubstituted quinoxalinyl
group, a substituted or unsubstituted naphthyridinyl group, a
substituted or unsubstituted benzoxazinyl group, a substituted or
unsubstituted benzothiazinyl group, a substituted or unsubstituted
acridinyl group, a substituted or unsubstituted phenazinyl group, a
substituted or unsubstituted phenothiazinyl group, a substituted or
unsubstituted phenoxazinyl group, a substituted or unsubstituted
fluorenyl group, a substituted or unsubstituted dibenzofuranyl
group, a substituted or unsubstituted dibenzothiopheneyl group, a
substituted or unsubstituted carbazole group, or a combination
thereof, but are not limited thereto.
[0038] In the specification, hole characteristics refer to
characteristics capable of donating an electron to form a hole when
electric field is applied, and characteristics that hole formed in
the anode is easily injected into the emission layer and
transported in the emission layer due to conductive characteristics
according to HOMO level.
[0039] In addition, electron characteristics refer to
characteristics capable of accepting an electron when electric
field is applied, and characteristics that electron formed in the
cathode is easily injected into the emission layer and transported
in the emission layer due to conductive characteristics according
to LUMO level.
[0040] Hereinafter, a composition according to one embodiment is
described.
[0041] The composition according to one embodiment includes at
least two kinds of host compounds and a dopant, and the host
compounds include a first host compound having bipolar
characteristics having relatively stronger electron characteristics
and a second host compound having bipolar characteristics having
relatively stronger hole characteristics.
[0042] The first host compound is a compound having bipolar
characteristics having relatively stronger electron
characteristics, and represented by the following Chemical Formula
1.
##STR00003##
[0043] In the above Chemical Formula 1,
[0044] Z is independently N or CR.sup.a,
[0045] at least one of Z is N,
[0046] R.sup.1 to R.sup.10 and R.sup.a are independently hydrogen,
deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a
substituted or unsubstituted C6 to C12 aryl group, or a combination
thereof,
[0047] in the above Chemical Formula 1, the total number of
6-membered rings substituting the triphenylene group is less than
or equal to 6,
[0048] L is a substituted or unsubstituted phenylene group, a
substituted or unsubstituted biphenylene group or a substituted or
unsubstituted terphenylene group,
[0049] n1 to n3 are independently 0 or 1, and
n1+n2+n3.gtoreq.1.
[0050] The 6-membered rings substituting the triphenylene group
indicate all the 6-membered rings directly or indirectly linked to
the triphenylene group and include 6-membered rings consisting of a
carbon atom, a nitrogen atom, or a combination thereof.
[0051] The first host compound may be represented by for example
the following Chemical Formula 1-I or 1-II depending on the bonding
position of the triphenylene group.
##STR00004##
[0052] In the above Chemical Formula 1-I or 1-II, Z, R.sup.1 to
R.sup.10, L and n1 to n3 are the same as described above.
[0053] The first host compound includes the triphenylene group and
at least one nitrogen-containing heteroaryl group.
[0054] The first host compound includes at least one
nitrogen-containing ring and thereby, may have a structure of
easily accepting electrons when an electric field is applied
thereto and thus, decrease a driving voltage of an organic
optoelectric device including the first host compound.
[0055] In addition, the first host compound has a bipolar structure
by including both a triphenylene moiety of easily accepting holes
and a nitrogen-containing ring moiety of easily accepting electrons
and may appropriately balance a flow of the holes and the
electrons, and accordingly, improve efficiency of an organic
optoelectric device when applied thereto.
[0056] The first host compound represented by the above Chemical
Formula 1 has at least one kink structure as a center of an arylene
group and/or a heteroarylene group.
[0057] The kink structure is a structure that two linking parts of
the arylene group and/or the heteroarylene group are not a linear
structure. For example, as for phenylene, ortho phenylene
o-phenylene) and meta phenylene (m-phenylene) have the kink
structure where two linking parts do not form a linear structure,
while para phenylene (p-phenylene) has no kink structure because
where two linking parts form a linear structure.
[0058] In the above Chemical Formula 1, the kink structure may be
formed as a center of a linking group (L) and/or an arylene group/a
heteroarylene group.
[0059] For example, when n1 in the above Chemical Formula 1 is 0,
that is, there is no linking group (L), a kink structure may be
formed as a center of an arylene group/a heteroarylene group, and
for example, the compound may be represented by the following
Chemical Formula 1a or 1b.
##STR00005##
[0060] In the above Chemical Formula 1a or 1b, Z, R.sup.1 to
R.sup.10 and L are the same as described above.
[0061] For example, when n1 in the above Chemical Formula 1 is 1, a
kink structure may be formed as a center of a linking group (L),
and for example, the L is may be a substituted or unsubstituted
phenylene having the kink structure, a substituted or unsubstituted
biphenylene group having the kink structure, or a substituted or
unsubstituted terphenylene group having the kink structure. The L
may be selected from, for example substituted or unsubstituted
groups listed in the following Group 1.
##STR00006## ##STR00007##
[0062] In the Group 1,
[0063] R.sup.15 to R.sup.42 are independently hydrogen, deuterium,
a substituted or unsubstituted C1 to C10 alkyl group, a substituted
or unsubstituted C3 to C30 cycloalkyl group, a substituted or
unsubstituted C3 to C30 heterocycloalkyl group, a substituted or
unsubstituted C6 to C30 aryl group, a substituted or unsubstituted
C2 to C30 heteroaryl group, a substituted or unsubstituted amine
group, a substituted or unsubstituted C6 to C30 arylamine group, a
substituted or unsubstituted C6 to C30 heteroarylamine group, a
substituted or unsubstituted C1 to C30 alkoxy group, a halogen, a
halogen-containing group, a cyano group, a hydroxyl group, an amino
group, a nitro group, a carboxyl group, ferrocenyl group, or a
combination thereof.
[0064] The first host compound may have at least two kink
structures and for example, two to four kink structures.
[0065] The first host compound may appropriately localize charges,
which are electrons and holes, and control a conjugation-system
flow due to the above kink structure, and thus improve a life-span
of an organic optoelectric device to which the composition is
applied.
[0066] In addition, in Chemical Formula 1, the total number of
6-membered rings substituting the triphenylene group is limited to
be less than or equal to 6, and thereby thermal decomposition of
the compound by a high temperature during a deposition process may
be decreased.
[0067] In addition, the first host compound may be effectively
prevented from stacking due to the structure and improve process
stability and simultaneously, lower a deposition temperature. This
stacking prevention effect may be further increased when the
compound includes the linking group (L) of the above Chemical
Formula 1.
[0068] The first host compound may be represented by one of, for
example the following Chemical Formulae 1c to 1t.
##STR00008## ##STR00009## ##STR00010## ##STR00011## ##STR00012##
##STR00013##
[0069] In the above Chemical Formulae 1c to 1t,
[0070] Z and R.sup.1 to R.sup.10 are the same as described above,
and
[0071] R.sup.60 to R.sup.77 are independently hydrogen, deuterium,
a substituted or unsubstituted C1 to C10 alkyl group, a substituted
or unsubstituted C3 to C30 cycloalkyl group, a substituted or
unsubstituted C3 to C30 heterocycloalkyl group, a substituted or
unsubstituted C6 to C30 aryl group, a substituted or unsubstituted
C2 to C30 heteroaryl group, a substituted or unsubstituted amine
group, a substituted or unsubstituted C6 to C30 arylamine group, a
substituted or unsubstituted C6 to C30 heteroarylamine group, a
substituted or unsubstituted C1 to C30 alkoxy group, a halogen, a
halogen-containing group, a cyano group, a hydroxyl group, an amino
group, a nitro group, a carboxyl group, a ferrocenyl group, or a
combination thereof.
[0072] The first host compound may be, for example, a compound
listed in the following Group 2, but is not limited thereto.
##STR00014## ##STR00015## ##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##
[0073] At least one or more kinds of the first host compound may be
used.
[0074] The second host compound is represented by the following
Chemical Formula 2.
##STR00050##
[0075] In the above Chemical Formula 2,
[0076] Y.sup.1 is a single bond, a substituted or unsubstituted C1
to C20 alkylene group, a substituted or unsubstituted C2 to C20
alkenylene group, a substituted or unsubstituted C6 to C30 arylene
group, a substituted or unsubstituted C2 to C30 heteroarylene
group, or a combination thereof,
[0077] Ar.sup.1 is a substituted or unsubstituted C6 to C30 aryl
group, a substituted or unsubstituted C2 to C30 heteroaryl group,
or a combination thereof,
[0078] R.sup.11 to R.sup.14 are independently hydrogen, deuterium,
a substituted or unsubstituted C1 to C20 alkyl group, a substituted
or unsubstituted C6 to C50 aryl group, a substituted or
unsubstituted C2 to C50 heteroaryl group, or a combination thereof,
and
[0079] at least one of R.sup.11 to R.sup.14 and Ar.sup.1 includes a
substituted or unsubstituted triphenylene group or a substituted or
unsubstituted carbazole group.
[0080] The second host compound is a compound having bipolar
characteristics in which hole characteristics are relatively
stronger than electron charaterictics and thus, increases charge
mobility and stability when used with the first host compound and
resultantly, may improve luminous efficiency and life-span
characteristics.
[0081] The second host compound may be, for example represented by
at least one of the following Chemical Formulae 2-I to 2-III.
##STR00051##
[0082] In the above Chemical Formulae 2-I to 2-III,
[0083] Y.sup.1 to Y.sup.3 are independently a single bond, a
substituted or unsubstituted C1 to C20 alkylene group, a
substituted or unsubstituted C2 to C20 alkenylene group, a
substituted or unsubstituted C6 to C30 arylene group, a substituted
or unsubstituted C2 to C30 heteroarylene group, or a combination
thereof,
[0084] Ar.sup.1 and Ar.sup.2 are independently a substituted or
unsubstituted C6 to C30 aryl group, a substituted or unsubstituted
C2 to C30 heteroaryl group, or a combination thereof, and
[0085] R.sup.11 to R.sup.14 and R.sup.43 to R.sup.54 are
independently hydrogen, deuterium, a substituted or unsubstituted
C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50
aryl group, a substituted or unsubstituted C2 to C50 heteroaryl
group, or a combination thereof.
[0086] The second host compound represented by the above Chemical
Formula 2-I has a structure where two carbazole groups having a
substituent are linked to each other.
[0087] Ar.sup.1 and Ar.sup.2 of the above Chemical Formula 2-I are
a substituent having electron or hole characteristics, and may be,
for example a substituted or unsubstituted phenyl group, a
substituted or unsubstituted biphenyl group, a substituted or
unsubstituted terphenyl group, a substituted or unsubstituted
naphthyl group, a substituted or unsubstituted anthracenyl group, a
substituted or unsubstituted carbazolyl group, a substituted or
unsubstituted benzofuranyl group, a substituted or unsubstituted
benzothiophenyl group, a substituted or unsubstituted fluorenyl
group, a substituted or unsubstituted pyridyl group, a substituted
or unsubstituted pyrimidinyl group, a substituted or unsubstituted
pyrazinyl group, a substituted or unsubstituted triazinyl group, a
substituted or unsubstituted triphenylene group, a substituted or
unsubstituted dibenzofuranyl group, a substituted or unsubstituted
dibenzothiopheneyl group, or a combination thereof.
[0088] At least one of Ar.sup.1 and Ar.sup.2 of the above Chemical
Formula 2-I may be, for example a substituent having electron
characteristics, and may be, for example a substituent represented
by the following Chemical Formula A.
##STR00052##
[0089] In the above Chemical Formula A,
[0090] Z is independently N or CR.sup.b,
[0091] A1 and A2 are independently a substituted or unsubstituted
C6 to C30 aryl group, a substituted or unsubstituted C3 to C30
heteroaryl group, or a combination thereof,
[0092] at least one of the Z, A1 and A2 includes N, and
[0093] a and b are independently 0 or 1.
[0094] The substituent represented by the above Chemical Formula A
may be, for example a functional group listed in the following
Group 3.
##STR00053## ##STR00054## ##STR00055## ##STR00056##
[0095] In addition, at least one of Ar.sup.1 and Ar.sup.2 of the
above Chemical Formula 2-I may be, for example a substituent having
hole characteristics, and may be, for example substituents listed
in the following Group 4.
##STR00057## ##STR00058##
[0096] The compound represented by the above Chemical Formula 2-I
may be, for example compounds selected from compounds listed in the
following Group 5, but is not limited thereto.
##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063##
##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068##
##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073##
##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078##
##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083##
##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088##
##STR00089##
[0097] A compound represented by the above Chemical Formula 2-II or
2-III has a structure where a substituted or unsubstituted
carbazole group and a substituted or unsubstituted triphenylene
group are bonded.
[0098] The Ar.sup.1 of the above Chemical Formula 2-II is a
substituent having hole or electron characteristics, and may be,
for example a substituted or unsubstituted phenyl group, a
substituted or unsubstituted biphenyl group, a substituted or
unsubstituted terphenyl group, a substituted or unsubstituted
naphthyl group, a substituted or unsubstituted anthracenyl group, a
substituted or unsubstituted carbazolyl group, a substituted or
unsubstituted benzofuranyl group, a substituted or unsubstituted
benzothiophenyl group, a substituted or unsubstituted fluorenyl
group, a substituted or unsubstituted pyridyl group, a substituted
or unsubstituted pyrimidinyl group, a substituted or unsubstituted
pyrazinyl group, a substituted or unsubstituted triazinyl group, a
substituted or unsubstituted triphenylene group, a substituted or
unsubstituted dibenzothiopheneyl group, a substituted or
unsubstituted dibenzofuranyl group, or a combination thereof.
[0099] The compound represented by the above Chemical Formula 2-II
may be, for example compounds selected from compounds listed in the
following Group 6, but is not limited thereto.
##STR00090## ##STR00091## ##STR00092## ##STR00093##
##STR00094##
[0100] The compound represented by the above Chemical Formula 2-III
may be, for example compounds selected from the following Group 7,
but is not limited thereto.
##STR00095## ##STR00096## ##STR00097## ##STR00098##
##STR00099##
[0101] At least one or more kinds of the second host compound may
be used.
[0102] The first and second host compounds may be variously
combined and thus, provide various compositions.
[0103] As described above, since the first host compound has
bipolar characteristics in which electron characteristics are
relatively strong, while the second host compound has bipolar
characteristics in which hole characteristic is relatively strong,
the first and second host compounds may be used together to
increase mobility of electrons and holes and thus, to remarkably
improve luminous efficiency compared with when the first and second
host compounds are used alone.
[0104] When the material having only electron or hole
characteristics is used to form an emission layer, excitons are
relatively more produced due to recombination of electrons and
holes at the interface of the emission layer and the electron
transport layer (ETL) or hole transport layer (HTL). As a result,
the excitons in the emission layer may interact with the exitons
produced at the interface of of the emission layer and the electron
transport layer (ETL) or hole transport layer (HTL) and thus, may
cause a roll-off, which is that luminous efficiency is sharply
deteriorated and thus, light emitting life-span characteristics is
also sharply deteriorated. In order to solve this problem, the
first and second host compounds are simultaneously introduced into
the emission layer to balance carriers in the emission layer, so
that a light emitting area may not be either the interface of the
emission layer and the electron transport layer or hole transport
layer (HTL) and thus, remarkably improving roll-off and
simultaneously life-span characteristics.
[0105] The first host compound and the second host compound may be
included in a weight ratio of, for example 1:10 to 10:1. Within the
range, bipolar characteristics may be realized more efficiently and
efficiency and life-span may be improved.
[0106] The composition may further include at least one host
compound except the above first host compound and the second host
compound.
[0107] The composition may further include a dopant. The dopant may
be a red, green, or blue dopant, for example a phosphorescent
dopant.
[0108] The dopant is mixed with the first host compound and the
second host compound in a small amount to cause light emission, and
may be generally a material such as a metal complex that emits
light by multiple excitation into a triplet or more. The dopant may
be, for example an inorganic, organic, or organic/inorganic
compound, and one or more kinds thereof may be used.
[0109] Examples of the phosphorescent dopant may be an organic
metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe,
Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent
dopant may be, for example a compound represented by the following
Chemical Formula Z, but is not limited thereto.
L.sub.2MX [Chemical Formula Z]
[0110] In the above Chemical Formula Z, M is a metal, and L and X
are the same or different, and are a ligand to form a complex
compound with M.
[0111] The M may be, for example Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb,
Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and the L and
X may be, for example a bidentate ligand.
[0112] The composition may form a film using a dry film-forming
method such as chemical vapor deposition or a solution method.
[0113] Hereinafter, an organic optoelectric device to which the
composition is applied is described.
[0114] The organic optoelectric device may be any device to convert
electrical energy into photoenergy and vice versa without
particular limitation, and may be, for example an organic
photoelectric device, an organic light emitting diode, an organic
solar cell, and an organic photo-conductor drum.
[0115] The organic optoelectric device includes an anode and a
cathode facing each other, and at least one organic layer
interposed between the anode and the cathode, wherein the organic
layer includes the above composition.
[0116] Herein, an organic light emitting diode as one example of an
organic optoelectric device is described referring to drawings.
[0117] FIGS. 1 and 2 are cross-sectional views of each organic
light emitting diode according to one embodiment.
[0118] Referring to FIG. 1, an organic light emitting diode 100
according to one embodiment includes an anode 120 and a cathode 110
facing each other and an organic layer 105 interposed between the
anode 120 and cathode 110.
[0119] The anode 120 may be made of a conductor having a high work
function to help hole injection, and may be for example metal,
metal oxide and/or a conductive polymer. The anode 120 may be, for
example a metal nickel, platinum, vanadium, chromium, copper, zinc,
gold, and the like or an alloy thereof; metal oxide such as zinc
oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide
(IZO), and the like; a combination of metal and oxide such as ZnO
and Al or SnO2 and Sb; 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.
[0120] The cathode 110 may be made of a conductor having a low work
function to help electron injection, and may be for example metal,
metal oxide and/or a conductive polymer. The cathode 110 may be for
example a metal or an alloy thereof such as magnesium, calcium,
sodium, potassium, titanium, indium, yttrium, lithium, gadolinium,
aluminum silver, tin, lead, cesium, barium, and the like; a
multi-layer structure material such as LiF/Al, LiO2/Al, LiF/Ca,
LiF/Al and BaF2/Ca, but is not limited thereto.
[0121] The organic layer 105 may include an emission layer 130
including the above composition.
[0122] The emission layer 130 may include, for example the above
composition.
[0123] Referring to FIG. 2, an organic light emitting diode 200
further includes a hole auxiliary layer 140 as well as an emission
layer 230. The hole auxiliary layer 140 may further increase hole
injection and/or hole mobility between the anode 120 and emission
layer 230 and block electrons. The hole auxiliary layer 140 may be,
for example a hole transport layer (HTL), a hole injection layer
(HIL), and/or an electron blocking layer, and may include at least
one layer.
[0124] In one embodiment, an organic light emitting diode may
further include an electron transport layer (ETL), an electron
injection layer (EIL), a hole injection layer (HIL), and the like,
as an organic layer 105 in FIG. 1 or FIG. 2.
[0125] The organic light emitting diodes 100 and 200 may be
manufactured by forming an anode or a cathode on a substrate,
forming an organic layer in accordance with a dry coating method
such as evaporation, sputtering, plasma plating, and ion plating;
and forming a cathode or an anode thereon.
[0126] The organic light emitting diode may be applied to an
organic light emitting diode (OLED) display.
MODE FOR INVENTION
[0127] Hereinafter, the embodiments are illustrated in more detail
with reference to examples. These examples, however, are not in any
sense to be interpreted as limiting the scope of the invention.
Synthesis of First Host Compound
Synthesis Example 1
Synthesis of Intermediate I-1
##STR00100##
[0129] 100 g (326 mmol) of 2-bromotriphenylene was dissolved in 1 L
of dimethylformamide (DMF) under a nitrogen environment, 99.2 g
(391 mmol) of bis(pinacolato)diboron, 2.66 g (3.26 mmol) of
1,1'-bis(diphenylphosphine)dichloropalladium (II), and 80 g (815
mmol) of potassium acetate were added thereto, and the mixture was
heated and refluxed at 150.degree. C. for 5 hours. When the
reaction was complete, water was added to the reaction solution,
and the mixture was filtered and then, dried in a vacuum oven. The
obtained residue was separated and purified through flash column
chromatography, obtainin 113 g (98%) of the compound I-1.
[0130] HRMS (70 eV, EI+): m/z calcd for C24H23BO2: 354.1791. found:
354.
[0131] Elemental Analysis: C, 81%; H, 7%
Synthesis Example 2
Synthesis of Intermediate I-2
##STR00101##
[0133] 32.7 g (107 mmol) of 2-bromotriphenylene was dissolved in
0.3 L of tetrahydrofuran (THF) in a nitrogen environment, 20 g (128
mmol) of 3-chlorophenyl boronic acid and 1.23 g (1.07 mmol) of
tetrakis(triphenylphosphine)palladium were added thereto, and the
mixture was agitated. 36.8 g (267 mmol) of potassium carbonate
saturated in water was added to the agitated resultant, and the
resulting mixture was heated and refluxed at 80.degree. C. for 24
hours. When the reaction was complete, water was added to the
reaction solution, the mixture was extracted with dichloromethane
(DCM), and the extract was treated with anhydrous MgSO.sub.4 to
remove moisture therefrom, filtered, and concentrated under a
reduced pressure. The obtained residue was separated and purified
through flash column chromatography, obtaining 22.6 g (63%) of the
compound I-2.
[0134] HRMS (70 eV, EI+): m/z calcd for C24H15Cl: 338.0862. found:
338.
[0135] Elemental Analysis: C, 85%; H, 5%
Synthesis Example 3
Synthesis of Intermediate I-3
##STR00102##
[0137] 22.6 g (66.7 mmol) of the compound I-2 was dissolved in 0.3
L of dimethylformamide (DMF) under a nitrogen environment, 25.4 g
(100 mmol) of bis(pinacolato)diboron, 0.54 g (0.67 mmol) of
(1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium (II), and
16.4 g (167 mmol) of potassium acetate were added thereto, and the
mixture was heated and refluxed at 150.degree. C. for 48 hours.
When the reaction was complete, water was added to the reaction
solution, and the mixture was filtered and dried in a vacuum oven.
The obtained residue was separated and purified through flash
column chromatography, obtaining 18.6 g (65%) of a compound
I-3.
[0138] HRMS (70 eV, EI+): m/z calcd for C30H27BO2: 430.2104. found:
430.
[0139] Elemental Analysis: C, 84%; H, 6%
Synthesis Example 4
Synthesis of Intermediate I-4
##STR00103##
[0141] 100 g (282 mmol) of the compound I-1 was dissolved in 1 L of
tetrahydrofuran (THF) under a nitrogen environment, 95.9 g (339
mmol) of 1-bromo-2-iodobenzene and 3.26 g (2.82 mmol) of
tetrakis(triphenylphosphine)palladium were added thereto, and the
mixture was agitated. 97.4 g (705 mmol) of potassium carbonate
saturated in water was added thereto, and the resulting mixture was
heated and refluxed at 80.degree. C. for 53 hours. When the
reaction was complete, water was added to the reaction solution,
the mixture was extracted with dichloromethane (DCM), and the
extract was treated with anhydrous MgSO.sub.4 to remove moisture
therefrom, filtered, and concentrated under a reduced pressure. The
obtained residue was separated and purified through flash column
chromatography, obtaining 95.1 g (88%) of the compound I-4.
[0142] HRMS (70 eV, EI+): m/z calcd for C24H15Br: 382.0357. found:
382.
[0143] Elemental Analysis: C, 75%; H, 4%
Synthesis Example 5
Synthesis of Intermediate I-5
##STR00104##
[0145] 90 g (235 mmol) of the compound I-4 was dissolved in 0.8 L
of dimethylformamide (DMF) under a nitrogen environment, 71.6 g
(282 mmol) of bis(pinacolato)diboron, 1.92 g (2.35 mmol) of
1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium (II), and
57.7 g (588 mmol) of potassium acetate were added thereto, and the
mixture was heated and refluxed at 150.degree. C. for 35 hours.
When the reaction was complete, water was added to the reaction
solution, and the mixture was filtered and dried in a vacuum oven.
The obtained residue was separated and purified through flash
column chromatography obtaining 74.8 g (74%) of the compound
I-5.
[0146] HRMS (70 eV, EI+): m/z calcd for C30H27BO2: 430.2104. found:
430.
[0147] Elemental Analysis: C, 84%; H, 6%
Synthesis Example 6
Synthesis of Intermediate I-6
##STR00105##
[0149] 50 g (116 mmol) of the compound I-3 was dissolved in 0.5 L
of tetrahydrofuran (THF) under a nitrogen environment, 39.4 g (139
mmol) of 1-bromo-3-iodobenzene and 1.34 g (1.16 mmol) of
tetrakis(triphenylphosphine)palladium were added thereto, and the
mixture was agitated. 40.1 g (290 mmol) of potassium carbonate
saturated in water was added thereto, and the resulting mixture was
heated and refluxed at 80.degree. C. for 12 hours. When the
reaction was complete, water was added to the reaction solution,
and the mixture was extracted with dichloromethane (DCM), and the
extract was treated with anhydrous MgSO.sub.4 to remove moisture
therefrom and then, filtered and concentrated under a reduced
pressure. This obtained residue was separated and purified through
flash column chromatography, obtaining 42.6 g (80%) of the compound
I-6.
[0150] HRMS (70 eV, EI+): m/z calcd for C30H19Br: 458.0670. found:
458.
[0151] Elemental Analysis: C, 78%; H, 4%
Synthesis Example 7
Synthesis of Intermediate I-7
##STR00106##
[0153] 40 g (87.1 mmol) of the compound I-6 was dissolved in 0.3 L
of dimethylformamide (DMF) under a nitrogen environment, 26.5 g
(104 mmol) of bis(pinacolato)diboron, 0.71 g (0.87 mmol) of
1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium (II), and
21.4 g (218 mmol) of potassium acetate were added thereto, and the
mixture was heated and refluxed at 150.degree. C. for 26 hours.
When the reaction was complete, water was added to the reaction
solution, and the mixture was filtered and dried in a vacuum oven.
The obtained residue was separated and purified through flash
column chromatography, obtaining 34 g (77%) of the compound
I-7.
[0154] HRMS (70 eV, EI+): m/z calcd for C36H31BO2: 506.2417. found:
506.
[0155] Elemental Analysis: C, 85%; H, 6%
Synthesis Example 8
Synthesis of Intermediate I-8
##STR00107##
[0157] 70 g (163 mmol) of the compound I-5 was dissolved in 0.6 L
of tetrahydrofuran (THF) in a nitrogen environment, 55.2 g (195
mmol) of 1-bromo-2-iodobenzene and 1.88 g (1.63 mmol) of
tetrakis(triphenylphosphine)palladium were added thereto, and the
mixture was agitated. 56.3 g (408 mmol) of potassium carbonate
saturated in water was added thereto, and the mixture was heated
and refluxed at 80.degree. C. for 12 hours. When the reaction was
complete, water was added to the reaction solution, the mixture was
extracted with dichloromethane (DCM), and the extract was treated
with anhydrous MgSO.sub.4 to remove moisture therefrom and then,
filtered and concentrated under a reduced pressure. This obtained
residue was separated and purified through flash column
chromatography, obtaining 68.1 g (91%) of the compound I-8.
[0158] HRMS (70 eV, EI+): m/z calcd for C30H19Br: 458.0670. found:
458.
[0159] Elemental Analysis: C, 78%; H, 4%
Synthesis Example 9
Synthesis of Intermediate I-9
##STR00108##
[0161] 40 g (87.1 mmol) of the compound I-8 was dissolved in 0.3 L
of dimethylformamide (DMF) under a nitrogen environment, 26.5 g
(104 mmol) of bis(pinacolato)diboron, 0.71 g (0.87 mmol) of
(1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium (II), and
21.4 g (218 mmol) of potassium acetate were added thereto, and the
mixture was heated and refluxed at 150.degree. C. for 23 hours.
When the reaction was complete, water was added to the reaction
solution, and the mixture was filtered and dried in a vacuum oven.
This obtained residue was separated and purified through flash
column chromatography, obtaining 30.4 g (69%) of the compound
I-9.
[0162] HRMS (70 eV, EI+): m/z calcd for C36H31BO2: 506.2417. found:
506.
[0163] Elemental Analysis: C, 85%; H, 6%
Synthesis Example 10
Synthesis of Intermediate I-10
##STR00109##
[0165] 30 g (59.2 mmol) of the compound I-9 was dissolved in 0.3 L
of tetrahydrofuran (THF) under a nitrogen environment, 20.1 g (71.1
mmol) of 1-bromo-2-iodobenzene and 0.68 g (0.59 mmol) of
tetrakis(triphenylphosphine)palladium were added thereto, and the
mixture was agitated. 20.5 g (148 mmol) of potassium carbonate
saturated in water was added thereto, and the mixture was heated
and refluxed at 80.degree. C. for 16 hours. When the reaction was
complete, water was added to the reaction solution, the mixture was
extracted with dichloromethane (DCM), and the extract was treated
with anhydrous MgSO.sub.4 to remove moisture therefrom and then,
filtered and concentrated under a reduced pressure. The obtained
residue was separated and purified through flash column
chromatography, obtaining 32.4 g (85%) of the compound I-10.
[0166] HRMS (70 eV, EI+): m/z calcd for C36H23Br: 534.0983. found:
534.
[0167] Elemental Analysis: C, 81%; H, 4%
Synthesis Example 11
Synthesis of Intermediate I-11
##STR00110##
[0169] 30 g (56 mmol) of the compound I-10 was dissolved in 0.3 L
of dimethylformamide (DMF) under a nitrogen environment, 17.1 g
(67.2 mmol) of bis(pinacolato)diboron, 0.46 g (0.56 mmol) of
(1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium (II), and
13.7 g (140 mmol) of potassium acetate were added thereto, and the
mixture was heated and refluxed at 150.degree. C. for 25 hours.
When the reaction was complete, water was added to the reaction
solution, and the mixture was filtered and dried in a vacuum oven.
The obtained residue was separated and purified through flash
column chromatography, obtaining 22.8 g (70%) of the compound
I-11.
[0170] HRMS (70 eV, EI+): m/z calcd for C42H35BO2: 582.2730. found:
582.
[0171] Elemental Analysis: C, 87%; H, 6%
Synthesis Example 12
Synthesis of Compound A-1
##STR00111##
[0173] 20 g (56.5 mmol) of the compound I-1 was dissolved in 0.2 L
of tetrahydrofuran (THF) in a nitrogen environment, 15.1 g (56.5
mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.65 g (0.57
mmol) of tetrakis(triphenylphosphine)palladium were added thereto,
and the mixture was agitated. 19.5 g (141 mmol) of potassium
carbonate saturated in water was added thereto, and the mixture was
heated and refluxed at 80.degree. C. for 20 hours. When the
reaction was complete, water was added to the reaction solution,
the mixture was extracted with dichloromethane (DCM), and the
extract was treated with anhydrous MgSO.sub.4 to remove moisture
therefrom and then, filtered and concentrated under a reduced
pressure. The obtained residue was separated and purified through
flash column chromatography, obtaining 22.1 g (85%) of the compound
A-1.
[0174] HRMS (70 eV, EI+): m/z calcd for C33H21N3459.1735. found:
459.
[0175] Elemental Analysis: C, 86%; H, 5%
Synthesis Example 13
Synthesis of Compound A-13
##STR00112##
[0177] 20 g (46.5 mmol) of the compound I-3 was dissolved in 0.2 L
of tetrahydrofuran (THF) under a nitrogen environment, 12.4 g (46.5
mmol) of 4-chloro-2,6-diphenylpyridine and 0.54 g (0.47 mmol) of
tetrakis(triphenylphosphine)palladium were added thereto, and the
mixture was agitated. 16.1 g (116 mmol) of potassium carbonate
saturated in water was added thereto, and the mixture was heated
and refluxed at 80.degree. C. for 17 hours. When the reaction was
complete, water was added to the reaction solution, the mixture was
extracted with dichloromethane (DCM), and the extract was treated
with anhydrous MgSO.sub.4 to remove moisture therefrom and then,
filtered and concentrated under a reduced pressure. This obtained
residue was separated and purified through flash column
chromatography, obtaining 18.9 g (76%) of the compound A-13.
[0178] HRMS (70 eV, EI+): m/z calcd for C41H27N: 533.2143. found:
533.
[0179] Elemental Analysis: C, 92%; H, 5%
Synthesis Example 14
Synthesis of Compound A-14
##STR00113##
[0181] 20 g (46.5 mmol) of the compound I-3 was dissolved in 0.2 L
of tetrahydrofuran (THF) under a nitrogen environment, 12.4 g (46.5
mmol) of 2-chloro-4,6-diphenylpyrimidine and 0.54 g (0.47 mmol) of
tetrakis(triphenylphosphine)palladium were added thereto, and the
mixture was agitated. 16.1 g (116 mmol) of potassium carbonate
saturated in water was added thereto, and the mixture was heated
and refluxed at 80.degree. C. for 15 hours. When the reaction was
complete, water was added to the reaction solution, the mixture was
extracted with dichloromethane (DCM), and the extract was treated
with anhydrous MgSO.sub.4 to remove moisture therefrom and then,
filtered and concentrated under a reduced pressure. The obtained
residue was separated and purified through flash column
chromatography, obtaining 20.4 g (82%) of the compound A-14.
[0182] HRMS (70 eV, EI+): m/z calcd for C40H26N2: 534.2096. found:
534.
[0183] Elemental Analysis: C, 90%; H, 5%
Synthesis Example 15
Synthesis of Compound A-15
##STR00114##
[0185] 20 g (46.5 mmol) of the compound I-3 was dissolved in 0.2 L
of tetrahydrofuran (THF) under a nitrogen environment, 12.4 g (46.5
mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.54 g (0.47
mmol) of tetrakis(triphenylphosphine)palladium were added thereto,
and the mixture was agitated. 16.1 g (116 mmol) of potassium
carbonate saturated in water was added thereto, and the mixture was
heated and refluxed at 80.degree. C. for 20 hours. When the
reaction was complete, water was added to the reaction solution,
the mixture was extracted with dichloromethane (DCM), and the
extract was treated with anhydrous MgSO.sub.4 to remove moisture
therefrom and filtered and then, concentrated under a reduced
pressure. The obtained residue was separated and purified through
flash column chromatography, obtaining 21.2 g (85%) of the compound
A-15.
[0186] HRMS (70 eV, EI+): m/z calcd for C39H25N3: 535.2048. found:
535.
[0187] Elemental Analysis: C, 87%; H, 5%
Synthesis Example 16
Synthesis of Compound A-24
##STR00115##
[0189] 20 g (46.5 mmol) of the compound I-5 was dissolved in 0.2 L
of tetrahydrofuran (THF) under a nitrogen environment, 12.4 g (46.5
mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.54 g (0.47
mmol) of tetrakis(triphenylphosphine)palladium were added thereto,
and the mixture was agitated. 16.1 g (116 mmol) of potassium
carbonate saturated in water was added thereto, and the mixture was
heated and refluxed at 80.degree. C. for 27 hours. When the
reaction was complete, water was added to the reaction solution,
the mixture was extracted with dichloromethane (DCM), and the
extract was treated with anhydrous MgSO.sub.4 to remove moisture
therefrom and then, filtered and concentrated under a reduced
pressure. This obtained residue was separated and purified through
flash column chromatography, obtaining 19.7 g (79%) of the compound
A-24.
[0190] HRMS (70 eV, EI+): m/z calcd for C39H25N3: 535.2048. found:
535.
[0191] Elemental Analysis: C, 87%; H, 5%
Synthesis Example 17
Synthesis of Compound A-33
##STR00116##
[0193] 20 g (39.5 mmol) of the compound I-7 was dissolved in 0.2 L
of tetrahydrofuran (THF) under a nitrogen environment, 10.6 g (39.5
mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.46 g (0.4 mmol)
of tetrakis(triphenylphosphine)palladium were added thereto, and
the mixture was agitated. 13.6 g (98.8 mmol) of potassium carbonate
saturated in water was added thereto, and the mixture was heated
and refluxed at 80.degree. C. for 23 hours. When the reaction was
complete, water was added to the reaction solution, the mixture was
extracted with dichloromethane (DCM), and the extract was treated
with anhydrous MgSO.sub.4 to remove moisture therefrom and then,
filtered and concentrated under a reduced pressure. The obtained
residue was separated and purified through flash column
chromatography, obtaining 17.9 g (74%) of the compound A-33.
[0194] HRMS (70 eV, EI+): m/z calcd for C45H29N3: 611.2361. found:
611.
[0195] Elemental Analysis: C, 88%; H, 5%
Synthesis Example 18
Synthesis of Compound A-69
##STR00117##
[0197] 20 g (39.5 mmol) of the compound I-9 was dissolved in 0.2 L
of tetrahydrofuran (THF) under a nitrogen environment, 10.6 g (39.5
mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.46 g (0.4 mmol)
of tetrakis(triphenylphosphine)palladium were added thereto, and
the mixture was agitated. 13.6 g (98.8 mmol) of potassium carbonate
saturated in water was added thereto, and the resulting mixture was
heated and refluxed at 80.degree. C. for 32 hours. When the
reaction was complete, water was added to the reaction solution,
the mixture was extracted with dichloromethane (DCM), and the
extract was treated with anhydrous MgSO.sub.4 to remove moisture
therefrom and then, filtered and concentrated under a reduced
pressure. This obtained residue was separated and purified through
flash column chromatography, obtaining 15.2 g (63%) the compound
A-69.
[0198] HRMS (70 eV, EI+): m/z calcd for C45H29N3: 611.2361. found:
611.
[0199] Elemental Analysis: C, 88%; H, 5%
Synthesis Example 19
Synthesis of Compound A-87
##STR00118##
[0201] 20 g (34.3 mmol) of the compound 1-11 was dissolved in 0.15
L of tetrahydrofuran (THF) under a nitrogen environment, 9.19 g
(34.3 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.4 g (0.34
mmol) of tetrakis(triphenylphosphine)palladium were added thereto,
and the mixture was agitated. 11.9 g (85.8 mmol) of potassium
carbonate saturated in water was added thereto, and the resulting
mixture was heated and refluxed at 80.degree. C. for 29 hours. When
the reaction was complete, water was added to the reaction
solution, the mixture was extracted with dichloromethane (DCM), and
the extract was treated with anhydrous MgSO.sub.4 to remove
moisture therefrom and then, filtered and concentrated under a
reduced pressure. The obtained residue was separated and purified
through flash column chromatography, obtaining 16.3 g (69%) of the
compound A-87.
[0202] HRMS (70 eV, EI+): m/z calcd for C51H33N3: 687.2674. found:
687.
[0203] Elemental Analysis: C, 89%; H, 5%
Synthesis 1 of Second Host Compound
Synthesis of Compound C-10
##STR00119##
[0205] 10 g (34.83 mmol) of phenylcarbazolyl boronic acid, 11.77 g
(38.31 mmol) of the compound 2, and 14.44 g (104.49 mmol) of
potassium carbonate, and 0.80 g (0.7 mmol) of
tetrakis-(triphenylphosphine)palladium (0) were suspended in 140 ml
of toluene and 50 ml of distilled water, and the suspended solution
was refluxed and agitated for 12 hours. Subsequently, the resultant
was extracted with dichloromethane and distilled water, and the
obtained organic layer was silica gel-filtered. Subsequently, after
removing an organic solution therefrom, a solid product was
obtained through a silica gel column with
hexane:dichloromethane=7:3(v/v) and then, recrystallized with
dichloromethane and n-hexane, obtaining 14.4 g (a yield: 88%) of a
compound C-10.
[0206] HRMS (70 eV, EI+): m/z calcd for C36H23N: 469.18. found:
469.
[0207] Elemental Analysis: C, 92%; H, 5%
Synthesis 2 of Second Host Compound
Synthesis of Compound B-10
##STR00120##
[0208] First Step: Synthesis of Compound J
[0209] 26.96 g (81.4 mmol) of N-phenyl carbazole-3-boronic acid
pinacolate and 23.96 g (97.36 mmol) of 3-bromo carbazole were mixed
with 230 mL of tetrahydrofuran and 100 ml of a 2 M-potassium
carbonate aqueous solution, and the mixture was heated and refluxed
under a nitrogen stream for 12 hours. When the reaction was
complete, a solid produced by pouring the reactant into methanol
was filtered and then, dissolved in chlorobenzene, activated carbon
and anhydrous magnesium sulfate were added thereto, and the mixture
was agitated. The solution was filtered and recrystallized by using
chlorobenzene and methanol, obtaining 22.6 g of a compound J (a
yield: 68%).
[0210] HRMS (70 eV, EI+): m/z calcd for C30H20N2: 408.16. found:
408.
[0211] Elemental Analysis: C, 88%; H, 5%
Second Step: Synthesis of Compound B-10
[0212] 22.42 g (54.88 mmol) of the compound J, 20.43 g (65.85 mmol)
of 2-bromo-4,6-diphenylpyridine, and 7.92 g (82.32 mmol) of
tertiarybutoxy sodium were dissolved in 400 ml of toluene, and 1.65
g (1.65 mmol) of palladium dibenzylideneamine and 1.78 g (4.39
mmol) of tertiarybutyl phosphorus were added in a dropwise fashion.
The reaction solution was heated and refluxed at 110.degree. C.
under a nitrogen stream for 12 hours. When the reaction was
complete, a solid produced by pouring methanol to the reactant was
filtered and then, dissolved in chlorobenzene, activated carbon and
anhydrous magnesium sulfate were added thereto, and the mixture was
agitated. The solution was filtered and recrystallized with
chlorobenzene and methanol, obtaining 28.10 g of a compound B-10 (a
yield: 80%).
[0213] HRMS (70 eV, EI+): m/z calcd for C47H31N3: 637.25. found:
637.
[0214] Elemental Analysis: C, 89%; H, 5%
Synthesis 3 of Second Host Compound
Synthesis of Compound B-31
##STR00121##
[0216] 9.97 g (30.95 mmol) of phenylcarbazolyl bromide, 9.78 g
(34.05 mmol) of phenylcarbazolyl boronic acid, 12.83 g (92.86 mmol)
of potassium carbonate, and 1.07 g (0.93 mmmol) of
tetrakis-(triphenylphosphine)palladium (0) were suspended in 120 ml
of toluene and 50 ml of distilled water, and the suspended solution
was refluxed and agitated for 12 hours. Subsequently, the resultant
was extracted with dichloromethane and distilled water, and an
organic layer was silica gel-filtered therefrom. Subsequently,
after removing an organic solution therefrom, a solid product
obtained therefrom was recrystallized with dichloromethane and
n-hexane, obtaining 13.8 g of a compound B-31 (a yield: 92%).
[0217] HRMS (70 eV, EI+): m/z calcd for C36H24N2: 484.19. found:
484.
[0218] Elemental Analysis: C, 89%; H, 5%
Synthesis 4 of Second Host Compound
Synthesis of Compound B-34
##STR00122##
[0220] 14.62 g (30.95 mmol) of triphenyl carbazolyl bromide, 9.78 g
(34.05 mmol) of phenylcarbazolyl boronic acid, 12.83 g (92.86 mmol)
of potassium carbonate, and 1.07 g (0.93 mmol) of
tetrakis-(triphenylphosphine)palladium (0) were suspended in 120 ml
of toluene and 50 ml of distilled water, and the suspended solution
was refluxed and agitated for 12 hours. Subsequently, the resultant
was extracted with dichloromethane and distilled water, and an
organic layer produced therein was silica gel-filtered.
Subsequently, a solid product obtained after removing an organic
solution therefrom was recrystallized with dichloromethane and
n-hexane, obtaining 16.7 g of a compound B-34 (a yield: 85%).
[0221] HRMS (70 eV, EI+): m/z calcd for C47H29N2: 621.23. found:
621.
[0222] Elemental Analysis: C, 91%; H, 5%
Synthesis 5 of Second Host Compound
Synthesis of Compound B-43
##STR00123##
[0224] 12.33 g (30.95 mmol) of biphenylcarbazolyl bromide, 12.37 g
(34.05 mmol) of biphenylcarbazolyl boronic acid, 12.83 g (92.86
mmol) of potassium carbonate, and 1.07 g (0.93 mmol) of
tetrakis-(triphenylphosphine)palladium (0) were suspended in 120 ml
of toluene and 50 ml of distilled water, and the suspended solution
was refluxed and agitated for 12 hours. Subsequently, the resultant
was extracted with dichloromethane and distilled water, and an
organic layer produced therein was silica gel-filtered.
Subsequently, a solid product obtained after removing an organic
solution therefrom was recrystallized with dichloromethane and
n-hexane, obtaining 18.7 g of a compound B-43 (a yield: 92%).
[0225] HRMS (70 eV, EI+): m/z calcd for C48H32N2: 636.26. found:
636.
[0226] Elemental Analysis: C, 91%; H, 5%
Manufacture of Organic Light Emitting Diode
Example 1
[0227] A glass substrate coated with ITO (Indium tin oxide) to be
1500 .ANG. thick was ultrasonic wave-washed with a distilled water.
Subsequently, the glass substrate was ultrasonic wave-washed with a
solvent such as isopropyl alcohol, acetone, methanol, and the like,
moved to a plasma cleaner, cleaned by using oxygen plasma for 10
minutes, and then, moved to a vacuum depositor. This obtained ITO
transparent electrode was used as a anode,
N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-diamin-
e) (a compound A) was vacuum-deposited on the ITO substrate upper
to form a 700 .ANG.-thick hole injection layer (HIL),
1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) (a
compound B) was deposited to be 50 .ANG.-thick on the injection
layer, and
N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-
-fluoren-2-amine (a compound C) was deposited to be 1020
.ANG.-thick to form a hole transport layer (HTL). On the hole
transport layer (HTL), a 400 .ANG.-thick emission layer was formed
by simultaneously using the synthesized compound A-33 and the
compound B-10 as a host, which was doped with 10 wt % of
tris(4-methyl-2,5-diphenylpyridine)iridium (III) (a compound D) as
a dopant. Herein, the compound A-33 and the compound B-10 were used
in a weight ratio of 4:1.
[0228] Subsequently,
8-(4-(4-(naphthalen-2-yl)-6-(naphthalen-3-yl)-1,3,5-triazin-2-yl)phenyl)q-
uinoline) (a compound E) and Liq were simultaneously
vacuum-deposited in a ratio of 1:1 on the emission layer upper to
form a 300 .ANG.-thick electron transport layer (ETL), and 15
.ANG.-thick Liq and 1200 .ANG.-thick Al were sequentially
vacuum-deposited to form a cathode on the electron transport layer
(ETL), manufacturing an organic light emitting diode.
[0229] The organic light emitting diode had a five-layered organic
thin film structure and specifically,
[0230] a structure of ITO/A 700 .ANG./B 50 .ANG./C 1020
.ANG./EML[A-33:B-10:D=X:X:10%] 400 .ANG./E:Liq 300 .ANG./Liq 15
.ANG./Al 1200 .ANG..
[0231] (X=a weight ratio)
Example 2
[0232] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound A-33
and the compound B-10 in a weight ratio of 1:1.
Example 3
[0233] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound A-33
and the compound B-10 in a weight ratio of 1:4.
Example 4
[0234] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound B-31
instead of the compound B-10.
Example 5
[0235] An organic light emitting diode was manufactured according
to the same method as Example 4 except for using the compound A-33
and the compound B-31 in a ratio of 1:1.
Example 6
[0236] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound C-10
instead of the compound B-10.
Example 7
[0237] An organic light emitting diode was manufactured according
to the same method as Example 6 except for using the compound A-33
and the compound C-10 in a weight ratio of 1:1.
Example 8
[0238] An organic light emitting diode was manufactured according
to the same method as Example 6 except for using the compound A-33
and the compound C-10 in a weight ratio of 1:4.
Example 9
[0239] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound B-34
instead of the compound B-10.
Example 10
[0240] An organic light emitting diode was manufactured according
to the same method as Example 9 except for using the compound A-33
and the compound B-34 in a weight ratio of 1:1.
Example 11
[0241] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound A-33
and the compound B-43 in a weight ratio of 1:1.
Comparative Example 1
[0242] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using
4,4'-di(9H-carbazol-9-yl)biphenyl (CBP) as a single host instead of
the two kinds of the compound A-33 and the compound B-10.
Comparative Example 2
[0243] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound A-33
as a single host instead of the two kinds of the compound A-33 and
the compound B-10.
Comparative Example 3
[0244] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound B-10
as a single host instead of the two kinds of the compound A-33 and
the compound B-10.
Comparative Example 4
[0245] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound B-31
as a single host instead of the two kinds of the compound A-33 and
the compound B-10.
Comparative Example 5
[0246] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound C-10
as a single host instead of the two kinds of the compound A-33 and
the compound B-10.
Comparative Example 6
[0247] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound B-34
as a single host instead of the two kinds of the compound A-33 and
the compound B-10.
Comparative Example 7
[0248] An organic light emitting diode was manufactured according
to the same method as Example 1 except for using the compound B-43
as a single host instead of the two kinds of the compound A-33 and
the compound B-10.
Evaluation
[0249] Luminous efficiency and life-span of each organic light
emitting diode according to Examples 1 to 11 and Comparative
Examples 1 to 7 were measured.
[0250] The measurements were specifically performed in the
following method, and the results were provided in the following
Table 1.
[0251] (1) Measurement of Current Density Change Depending on
Voltage Change
[0252] Current values flowing in the unit device of the
manufactured organic light emitting diodes were measured for, while
increasing the voltage from 0V to 10V using a current-voltage meter
(Keithley 2400), and the measured current values were divided by an
area to provide the results.
[0253] (2) Measurement of Luminance Change Depending on Voltage
Change
[0254] Luminance of the manufactured organic light emitting diodes
was measured for luminance, while increasing the voltage from 0V to
10V using a luminance meter (Minolta Cs-1000A).
[0255] (3) Measurement of Luminous Efficiency
[0256] Current efficiency (cd/A) at the same current density (10
mA/cm2) were calculated by using the luminance, current density,
and voltages obtained from items (1) and (2).
[0257] (4) Measurement of Roll-Off
[0258] An efficiency roll-off was calculated as a percentage by
using (Max value-value at 6000 cd/m.sup.2/Max value) in the
(3).
[0259] (5) Measurement of Life-Span
[0260] Luminance (cd/m.sup.2) was maintained at 6000 cd/m.sup.2 and
a time at current efficiency (cd/A) decreases to 97% was
measured.
TABLE-US-00001 TABLE 1 First Sec- host:Second Luminous Roll- Life-
First ond host efficiency off span host host (wt/wt) (cd/A) (%) T97
(h) Example 1 A-33 B-10 4:1 39.8 25.5 300 Example 2 A-33 B-10 1:1
45.1 17.3 350 Example 3 A-33 B-10 1:4 43.3 8.7 200 Example 4 A-33
B-31 4:1 45.6 19.2 350 Example 5 A-33 B-31 1:1 52.9 10.4 150
Example 6 A-33 C-10 4:1 38.6 27.5 350 Example 7 A-33 C-10 1:1 42.3
24.8 350 Example 8 A-33 C-10 1:4 46 17.5 220 Example 9 A-33 B-34
4:1 40.7 23.2 540 Example 10 A-33 B-34 1:1 47 14.4 630 Example 11
A-33 B-43 1:1 44 20.7 720 Comparative CBP -- 19.3 0.9 0.5 Example 1
Comparative A-33 -- 31.1 30.3 150 Example 2 Comparative B-10 --
34.8 6.2 10 Example 3 Comparative B-31 -- 2.3 2.5 -- Example 4
Comparative C-10 -- 15.3 4.1 10 Example 5 Comparative B-34 -- 17
3.8 10 Example 6 Comparative B-43 -- 2.6 1.4 10 Example 7 *
Impossible to measure life-span of a device having luminance of
less than or equal to 6000 cd/m.sup.2
[0261] Referring to Table 1, the organic light emitting diodes
according to Examples 1 to 11 showed remarkably improved luminous
efficiency, roll-off, and life-span characteristics compared with
the organic light emitting diodes according to Comparative Examples
1 to 7.
[0262] While this invention has been described in connection with
what is presently considered to be practical exemplary embodiments,
it is to be understood that the invention is not limited to the
disclosed embodiments, but, on the contrary, is intended to cover
various modifications and equivalent arrangements included within
the spirit and scope of the appended claims. Therefore, the above
embodiments should be understood to be exemplary but not limiting
the present invention in any way.
* * * * *