U.S. patent application number 17/526112 was filed with the patent office on 2022-03-10 for multi-component host material and organic electroluminescent device comprising the same.
The applicant listed for this patent is ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.. Invention is credited to Hee-Choon AHN, Young-Jun CHO, Kyung-Hoon CHOI, Chi-Sik KIM, Nam-Kyun KIM, Young-Kwang KIM, Kyung-Joo LEE, Seon-Woo LEE, Su-Hyun LEE, Doo-Hyeon MOON, Kyoung-Jin PARK, Jae-Hoon SHIM.
Application Number | 20220077405 17/526112 |
Document ID | / |
Family ID | |
Filed Date | 2022-03-10 |
United States Patent
Application |
20220077405 |
Kind Code |
A1 |
AHN; Hee-Choon ; et
al. |
March 10, 2022 |
MULTI-COMPONENT HOST MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE
COMPRISING THE SAME
Abstract
The present invention relates to an organic electroluminescent
device comprising at least one light-emitting layer between an
anode and a cathode, wherein the light-emitting layer comprises a
host and a phosphorescent dopant; the host consists of
multi-component host compounds; at least a first host compound of
the multi-component host compounds is a specific bicarbazole
derivative containing an aryl group, and a second host compound is
a specific carbazole derivative including a nitrogen-containing
heteroaryl group. According to the present invention, the organic
electroluminescent device using the multi-component host compounds
has a high efficiency and long lifespan compared with the
conventional device using one component host compound.
Inventors: |
AHN; Hee-Choon;
(Gyeonggi-do, KR) ; KIM; Young-Kwang;
(Gyeonggi-do, KR) ; MOON; Doo-Hyeon; (Gyeonggi-do,
KR) ; LEE; Su-Hyun; (Gyeonggi-do, KR) ; LEE;
Seon-Woo; (Gyeonggi-do, KR) ; KIM; Chi-Sik;
(Gyeonggi-do, KR) ; PARK; Kyoung-Jin;
(Gyeonggi-do, KR) ; KIM; Nam-Kyun; (Gyeonggi-do,
KR) ; CHOI; Kyung-Hoon; (Gyeonggi-do, KR) ;
SHIM; Jae-Hoon; (Seoul, KR) ; CHO; Young-Jun;
(Gyeonggi-do, KR) ; LEE; Kyung-Joo; (Seoul,
KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD. |
Chungcheongnam-do |
|
KR |
|
|
Appl. No.: |
17/526112 |
Filed: |
November 15, 2021 |
Related U.S. Patent Documents
|
|
|
|
|
|
Application
Number |
Filing Date |
Patent Number |
|
|
15301978 |
Oct 5, 2016 |
|
|
|
PCT/KR2015/003485 |
Apr 7, 2015 |
|
|
|
17526112 |
|
|
|
|
International
Class: |
H01L 51/00 20060101
H01L051/00; C09K 11/06 20060101 C09K011/06; C09K 11/02 20060101
C09K011/02 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 8, 2014 |
KR |
10-2014-0041844 |
Jul 10, 2014 |
KR |
10-2014-0086754 |
Mar 26, 2015 |
KR |
10-2015-0042704 |
Claims
1. An organic electroluminescent device comprising at least one
light-emitting layer between an anode and a cathode, wherein the
light-emitting layer comprises a host and a phosphorescent dopant;
the host consists of multi-component host compounds; at least a
first host compound of the multi-component host compounds is
represented by the following formula 1 which is a bicarbazole
derivative containing an aryl group, and a second host compound is
represented by the following formula 2 which is a carbazole
derivative including a nitrogen-containing heteroaryl group:
##STR00360## wherein A.sub.1 and A.sub.2 each independently
represent a deuterium substituted or unsubstituted (C6-C30)aryl
group; X.sub.1 to X.sub.16 each independently represent hydrogen,
deuterium, group, a substituted or unsubstituted (C1-C30)alkyl
group, group, a substituted or unsubstituted (C3-C30)cycloalkyl
group, a substituted or unsubstituted (C6-C60)aryl group, or a
substituted or unsubstituted 3- to 30-membered heteroaryl group; Ma
represents a substituted or unsubstituted nitrogen-containing 5- to
30-membered heteroaryl group; La represents a single bond, or a
substituted or unsubstituted (C6-C30)arylene group; Xa to Xh each
independently represent hydrogen, deuterium, a halogen, a cyano
group, a substituted or unsubstituted (C1-C30)alkyl group, a
substituted or unsubstituted (C2-C30)alkenyl group, a substituted
or unsubstituted (C2-C30)alkynyl group, a substituted or
unsubstituted (C3-C30)cycloalkyl group, a substituted or
unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3-
to 30-membered heteroaryl group selected from the group consisting
of furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl,
thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl,
triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl,
pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl,
isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl,
benzoimidazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl,
benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl,
quinoxalinyl, phenoxazinyl, phenanthridinyl, benzodioxolyl
benzothiazolyl, benzoisothiazolyl and benzoisoxazolyl, a
substituted or unsubstituted tri(C1-C30)alkylsilyl group, a
substituted or unsubstituted tri(C6-C30)arylsilyl group, a
substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl
group, or a substituted or unsubstituted mono- or
di-(C6-C30)arylamino group, with the proviso that at least one of
Xa to Xh is a substituted or unsubstituted 3- to 30-membered
heteroaryl group selected from the group consisting of
dibenzofuranyl and dibenzothiophenyl; or are linked between
adjacent substituents to form a substituted or unsubstituted mono-
or polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon
atom(s) ring may be replaced with at least one hetero atom selected
from nitrogen, oxygen and sulfur wherein the fused aromatic or
heteroaromatic ring is indole, indene, benzofuran and
benzothiophene, which may be further substituted with a
(C1-C10)alkyl group or a (C6-C15)aryl group; and the heteroaryl
group contains at least one hetero atom selected from B, N, O, S,
P(.dbd.O), Si and P.
2. The organic electroluminescent device according to claim 1,
wherein the compound of formula 1 is represented by the following
formula 3, 4, 5, or 6: ##STR00361## wherein A.sub.1 and A.sub.2
each independently represent a deuterium substituted or
unsubstituted (C6-C30)aryl group; and X.sub.1 to X.sub.16 each
independently represent hydrogen, deuterium, a halogen, a cyano
group, a substituted or unsubstituted (C1-C30)alkyl group, a
substituted or unsubstituted (C2-C30)alkenyl group, a substituted
or unsubstituted (C2-C30)alkynyl group, a substituted or
unsubstituted (C3-C30)cycloalkyl group, a substituted or
unsubstituted (C6-C60)aryl group, a substituted or unsubstituted 3-
to 30-membered heteroaryl group, a substituted or unsubstituted
tri(C1-C30)alkylsilyl group, a substituted or unsubstituted
tri(C6-C30)arylsilyl group, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or
unsubstituted mono- or di-(C6-C30)arylamino group; or are linked
between adjacent substituents to form a substituted or
unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring whose carbon atom(s) ring may be replaced with at least one
hetero atom selected from nitrogen, oxygen and sulfur.
3. The organic electroluminescent device according to claim 1,
wherein the compound of formula 2 is represented by the following
formula 7 or 8: ##STR00362## wherein V and W each independently
represent a single bond, NR.sub.15, CR.sub.16R.sub.17, S, or O,
provided that both V and W neither represent a single bond nor
represent NR.sub.15, A.sub.2 represents a substituted or
unsubstituted (C6-C30)aryl group and may be bonded to Xn or Xo,
L.sub.3 and L.sub.4 each independently represent a single bond, or
a substituted or unsubstituted (C6-C60)arylene group; Xi represents
hydrogen, deuterium, a halogen, a cyano group, a substituted or
unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted
(C2-C30)alkenyl group, a substituted or unsubstituted
(C2-C30)alkynyl group, a substituted or unsubstituted
(C3-C30)cycloalkyl group, a substituted or unsubstituted
(C6-C60)aryl group, a substituted or unsubstituted 3- to
30-membered heteroaryl group, a substituted or unsubstituted
tri(C1-C30)alkylsilyl group, a substituted or unsubstituted
tri(C6-C30)arylsilyl group, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or
unsubstituted mono- or di-(C6-C30)arylamino group; or are linked
between adjacent substituents to form a substituted or
unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring whose carbon atom(s) ring may be replaced with at least one
hetero atom selected from nitrogen, oxygen and sulfur; Xj to Xr
each independently represent hydrogen, deuterium, a halogen, a
cyano group, a carboxyl group, a nitro group, a hydroxyl group, a
substituted or unsubstituted (C1-C30)alkyl group, a substituted or
unsubstituted (C3-C30)cycloalkyl group, a substituted or
unsubstituted (C3-C30)cycloalkenyl group, a substituted or
unsubstituted 3- to 7-membered heterocycloalkyl group, a
substituted or unsubstituted (C6-C60)aryl group, a substituted or
unsubstituted 3- to 30-membered heteroaryl group,
--NR.sub.5R.sub.6, or --SiR.sub.7R.sub.8R.sub.9; or are linked
between adjacent substituents to form a substituted or
unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring whose carbon atom(s) ring may be replaced with at least one
hetero atom selected from nitrogen, oxygen and sulfur; Ma, La, and
Xe to Xh are as defined in formula 2; R.sub.5 to R.sub.9 each
independently represent hydrogen, deuterium, a halogen, a cyano
group, a carboxyl group, a nitro group, a hydroxyl group, a
substituted or unsubstituted (C1-C30)alkyl group, a substituted or
unsubstituted (C3-C30)cycloalkyl group, a substituted or
unsubstituted (C3-C30)cycloalkenyl group, a substituted or
unsubstituted 3- to 7-membered heterocycloalkyl group, a
substituted or unsubstituted (C6-C60)aryl group, or a substituted
or unsubstituted 3- to 30-membered heteroaryl group; or are linked
between adjacent substituents to form a substituted or
unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring whose carbon atom(s) ring may be replaced with at least one
hetero atom selected from nitrogen, oxygen and sulfur; R.sub.16 and
R.sub.17 each independently represent hydrogen, deuterium, a
halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl
group, a substituted or unsubstituted (C1-C30)alkyl group, a
substituted or unsubstituted (C3-C30)cycloalkyl group, a
substituted or unsubstituted (C3-C30)cycloalkenyl group, a
substituted or unsubstituted 3- to 7-membered heterocycloalkyl
group, a substituted or unsubstituted (C6-C60)aryl group, or a
substituted or unsubstituted 3- to 30-membered heteroaryl group;
and R.sub.15 represents hydrogen, deuterium, a halogen, a cyano
group, a carboxyl group, a nitro group, a hydroxyl group, a
substituted or unsubstituted (C1-C30)alkyl group, a substituted or
unsubstituted (C3-C30)cycloalkyl group, a substituted or
unsubstituted (C3-C30)cycloalkenyl group, a substituted or
unsubstituted 3- to 7-membered heterocycloalkyl group, a
substituted or unsubstituted (C6-C60)aryl group, or a substituted
or unsubstituted 3- to 30-membered heteroaryl group.
4. The organic electroluminescent device according to claim 1,
wherein La in formula 2 represents a single bond, or is represented
by one selected from the following formulas 10 to 19: ##STR00363##
##STR00364## wherein Xi to Xp each independently represent
hydrogen, deuterium, a halogen, a cyano group, a substituted or
unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted
(C2-C30)alkenyl group, a substituted or unsubstituted
(C2-C30)alkynyl group, a substituted or unsubstituted
(C3-C30)cycloalkyl group, a substituted or unsubstituted
(C6-C60)aryl group, a substituted or unsubstituted 3- to
30-membered heteroaryl group, a substituted or unsubstituted
tri(C1-C30)alkylsilyl group, a substituted or unsubstituted
tri(C6-C30)arylsilyl group, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or
unsubstituted mono- or di-(C6-C30)arylamino group; or are linked
between adjacent substituents to form a substituted or
unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring whose carbon atom(s) ring may be replaced with at least one
hetero atom selected from nitrogen, oxygen and sulfur.
5. The organic electroluminescent device according to claim 1,
wherein Ma in formula 2 is a monocyclic-based heteroaryl group
selected from the group consisting of pyrrolyl, imidazolyl,
pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl,
pyrazinyl, pyrimidinyl and pyridazinyl, or a fused ring-based
heteroaryl group selected from the group consisting of
benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl,
quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl,
quinoxalinyl, carbazolyl and phenanthridinyl.
6. The organic electroluminescent device according to claim 1,
wherein A.sub.1 and A.sub.2 in formula 1 each independently
represent phenyl, biphenyl, terphenyl, naphthyl, fluorenyl,
phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl,
tetracenyl, perylenyl, chrysenyl, naphthacenyl, or
fluoranthenyl.
7. The organic electroluminescent device according to claim 1,
wherein Xa to Xh in formula 2 each independently represent
hydrogen; a cyano group; a (C6-C15)aryl group which is
unsubstituted or substituted with a tri(C6-C10)arylsilyl group, or
a 10- to 20-membered heteroaryl group which is unsubstituted or
substituted with a (C6-C12)aryl group; or are linked between
adjacent substituents to form a substituted or unsubstituted
indole, a substituted or unsubstituted indene, a substituted or
unsubstituted benzofuran, or a substituted or unsubstituted
benzothiophene.
8. The organic electroluminescent device according to claim 1,
wherein the compound represented by formula 1 is selected from the
group consisting of the following compounds: ##STR00365##
##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370##
##STR00371## ##STR00372## ##STR00373## ##STR00374## ##STR00375##
##STR00376## ##STR00377## ##STR00378## ##STR00379## ##STR00380##
##STR00381## ##STR00382## ##STR00383## ##STR00384## ##STR00385##
##STR00386## ##STR00387## ##STR00388## ##STR00389## ##STR00390##
##STR00391## ##STR00392## ##STR00393## ##STR00394## ##STR00395##
##STR00396## ##STR00397## ##STR00398## ##STR00399## ##STR00400##
##STR00401## ##STR00402## ##STR00403## ##STR00404## ##STR00405##
##STR00406## ##STR00407## ##STR00408## ##STR00409## ##STR00410##
##STR00411## ##STR00412## ##STR00413## ##STR00414## ##STR00415##
##STR00416## ##STR00417## ##STR00418## ##STR00419## ##STR00420##
##STR00421## ##STR00422## ##STR00423## ##STR00424## ##STR00425##
##STR00426## ##STR00427## ##STR00428##
9. The organic electroluminescent device according to claim 1,
wherein the compound represented by formula 2 is selected from the
group consisting of the following compounds: ##STR00429##
##STR00430## ##STR00431## ##STR00432## ##STR00433## ##STR00434##
##STR00435## ##STR00436## ##STR00437## ##STR00438## ##STR00439##
##STR00440## ##STR00441## ##STR00442## ##STR00443## ##STR00444##
##STR00445## ##STR00446## ##STR00447## ##STR00448## ##STR00449##
##STR00450## ##STR00451## ##STR00452## ##STR00453## ##STR00454##
##STR00455## ##STR00456## ##STR00457## ##STR00458## ##STR00459##
##STR00460## ##STR00461## ##STR00462## ##STR00463## ##STR00464##
##STR00465## ##STR00466## ##STR00467## ##STR00468## ##STR00469##
##STR00470## ##STR00471## ##STR00472## ##STR00473## ##STR00474##
##STR00475## ##STR00476## ##STR00477## ##STR00478## ##STR00479##
##STR00480## ##STR00481## ##STR00482## ##STR00483## ##STR00484##
##STR00485## ##STR00486## ##STR00487## ##STR00488## ##STR00489##
##STR00490## ##STR00491## ##STR00492## ##STR00493## ##STR00494##
##STR00495## ##STR00496## ##STR00497## ##STR00498## ##STR00499##
##STR00500## ##STR00501## ##STR00502## ##STR00503## ##STR00504##
##STR00505## ##STR00506## ##STR00507## ##STR00508## ##STR00509##
##STR00510## ##STR00511## ##STR00512## ##STR00513## ##STR00514##
##STR00515## ##STR00516## ##STR00517## ##STR00518## ##STR00519##
##STR00520## ##STR00521## ##STR00522## ##STR00523## ##STR00524##
##STR00525## ##STR00526## ##STR00527## ##STR00528## ##STR00529##
##STR00530## ##STR00531## ##STR00532## ##STR00533## ##STR00534##
##STR00535## ##STR00536## ##STR00537## ##STR00538## ##STR00539##
##STR00540## ##STR00541## ##STR00542## ##STR00543## ##STR00544##
##STR00545## ##STR00546## ##STR00547## ##STR00548## ##STR00549##
##STR00550## ##STR00551## ##STR00552## ##STR00553## ##STR00554##
##STR00555## ##STR00556## ##STR00557## ##STR00558## ##STR00559##
##STR00560## ##STR00561## ##STR00562## ##STR00563## ##STR00564##
##STR00565## ##STR00566## ##STR00567## ##STR00568## ##STR00569##
##STR00570## ##STR00571## ##STR00572## ##STR00573## ##STR00574##
Description
CLAIM OF BENEFIT OF PRIOR APPLICATION
[0001] This application claims priority under 35 U.S.C. .sctn. 120
from U.S. patent application Ser. No. 15/301,978, filed Oct. 5,
2016, which is the National Stage Entry of PCT/KR2015/003485, filed
Apr. 7, 2015, both of which are incorporated by reference herein in
their entirety.
TECHNICAL FIELD
[0002] The present invention relates to a multi-component host
material and an organic electroluminescent device comprising the
same.
BACKGROUND ART
[0003] An electroluminescent (EL) device is a self-light-emitting
device with the advantage of providing a wider viewing angle, a
greater contrast ratio, and a faster response time. An organic EL
device was first developed by Eastman Kodak, by using small
aromatic diamine molecules and aluminum complexes as materials for
forming a light-emitting layer (see Appl. Phys. Lett. 51, 913,
1987).
[0004] The organic EL device changes electric energy into light by
the injection of a charge into an organic light-emitting material
and commonly comprises an anode, a cathode, and an organic layer
formed between the two electrodes. The organic layer of the organic
EL device may be composed of a hole injection layer (HIL), a hole
transport layer (HTL), an electron blocking layer (EBL), a
light-emitting layer (EML) (containing host and dopant materials),
an electron buffer layer, a hole blocking layer (HBL), an electron
transport layer (ETL), an electron injection layer (EIL), etc.; the
materials used in the organic layer can be classified into a hole
injection material, a hole transport material, an electron blocking
material, a light-emitting material, an electron buffer material, a
hole blocking material, an electron transport material, an electron
injection material, etc., depending on functions. In the organic EL
device, holes from an anode and electrons from a cathode are
injected into a light-emitting layer by the injection of a charge,
and an exciton having high energy is produced by the recombination
of holes and electrons. The organic light-emitting compound moves
into an excited state by the energy and emits light which changes
from energy when the organic light-emitting compound returns to the
ground state from the excited state.
[0005] The most important factor determining luminescent efficiency
in an organic EL device is the light-emitting material. The
light-emitting material is required to have the following features:
high quantum efficiency, high movement degree of an electron and a
hole, formability of a uniform layer, and stability. The
light-emitting material is classified into blue light-emitting
materials, green light-emitting materials, and red light-emitting
materials according to the light-emitting color, and further
includes yellow light-emitting materials or orange light-emitting
materials. Furthermore, the light-emitting material is classified
into a host material and a dopant material in the functional
aspect. Recently, an urgent task is the development of an organic
EL device having high efficacy and long operating lifespan. In
particular, the development of highly excellent light-emitting
material over conventional light-emitting materials is urgent
considering EL properties required in medium- and large-sized OLED
panels. For this, preferably, as a solvent in a solid state and
energy transmitter, a host material should have high purity and
suitable molecular weight in order to be deposited under vacuum.
Furthermore, a host material is required to have high glass
transition temperature and pyrolysis temperature to guarantee
thermal stability, high electrochemical stability to provide long
lifespan, easy formability of an amorphous thin film, good adhesion
with adjacent layers, and no movement between layers.
[0006] A mixed system of a dopant/host material can be used as a
light-emitting material to improve color purity, luminescent
efficiency, and stability. Generally, the device having the most
excellent EL properties comprises the light-emitting layer, wherein
a dopant is doped onto a host. If the dopant/host material system
is used, the selection of the host material is important since the
host material greatly influences on efficiency and performance of a
light-emitting device.
[0007] WO 2013/168688 A1, Japanese Patent No. 3139321, Korean
Patent No. 10-1170666, Korean Patent Application Laying-open No.
10-2012-0013173, and WO 2013/112557 A1 disclose organic EL devices
comprising a dopant/host material system. The above literature use
one host component having a carbazole-carbazole skeleton or exclude
a host having a cabazole skeleton from second and third hosts.
[0008] The present inventors have found that an organic EL device
using a multi-component host compounds having a specific
bicarbazole derivative which contains an aryl group and a specific
carbazole derivative which includes a nitrogen-containing
heteroaryl group has high efficiency and long lifespan, compared
with using one component host compound in a light-emitting
layer.
DISCLOSURE OF THE INVENTION
Problems to be Solved
[0009] The object of the present invention is to provide an organic
EL device having high efficiency and long lifespan.
Solution to Problems
[0010] The above objective can be achieved by an organic
electroluminescent device comprising at least one light-emitting
layer between an anode and a cathode, wherein the light-emitting
layer comprises a host and a phosphorescent dopant; the host
consists of multi-component host compounds; at least a first host
compound of the multi-component host compounds is represented by
the following formula 1 which is a specific bicarbazole derivative
containing an aryl group, and a second host compound is represented
by the following formula 2 which is a specific carbazole derivative
including a nitrogen-containing heteroaryl group:
##STR00001##
[0011] wherein
[0012] A.sub.1 and A.sub.2 each independently represent a
substituted or unsubstituted (C6-C30)aryl group;
[0013] X.sub.1 to X.sub.16 each independently represent hydrogen,
deuterium, a halogen, a cyano group, a substituted or unsubstituted
(C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl
group, a substituted or unsubstituted (C2-C30)alkynyl group, a
substituted or unsubstituted (C3-C30)cycloalkyl group, a
substituted or unsubstituted (C6-C60)aryl group, a substituted or
unsubstituted 3- to 30-membered heteroaryl group, a substituted or
unsubstituted tri(C1-C30)alkylsilyl group, a substituted or
unsubstituted tri(C6-C30)arylsilyl group, a substituted or
unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or a
substituted or unsubstituted mono- or di-(C6-C30)arylamino group;
or are linked between adjacent substituents to form a substituted
or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or
aromatic ring whose carbon atom(s) may be replaced with at least
one hetero atom selected from nitrogen, oxygen and sulfur;
[0014] Ma represents a substituted or unsubstituted
nitrogen-containing 5- to 30-membered heteroaryl group;
[0015] La represents a single bond, or a substituted or
unsubstituted (C6-C30)arylene group;
[0016] Xa to Xh each independently represent hydrogen, deuterium, a
halogen, a cyano group, a substituted or unsubstituted
(C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl
group, a substituted or unsubstituted (C2-C30)alkynyl group, a
substituted or unsubstituted (C3-C30)cycloalkyl group, a
substituted or unsubstituted (C6-C60)aryl group, a substituted or
unsubstituted 3- to 30-membered heteroaryl group, a substituted or
unsubstituted tri(C1-C30)alkylsilyl group, a substituted or
unsubstituted tri(C6-C30)arylsilyl group, a substituted or
unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or a
substituted or unsubstituted mono- or di-(C6-C30)arylamino group;
or are linked between adjacent substituents to form a substituted
or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or
aromatic ring whose carbon atom(s) ring may be replaced with at
least one hetero atom selected from nitrogen, oxygen and
sulfur;
[0017] the fused aromatic or heteroaromatic ring is selected from
the group consisting of benzene, indole, indene, benzofuran and
benzothiophene, which may be further substituted with a
(C1-C10)alkyl group or a (C6-C15)aryl group; and
[0018] the heteroaryl group contains at least one hetero atom
selected from B, N, O, S, P(.dbd.O), Si and P.
Effects of the Invention
[0019] According to the present invention, the organic EL device
having high efficiency and long lifespan is provided and the
production of a display device or a lighting device is possible by
using the organic EL device.
EMBODIMENTS OF THE INVENTION
[0020] Hereinafter, the present invention will be described in
detail. However, the following description is intended to explain
the invention, and is not meant in any way to restrict the scope of
the invention.
[0021] The compound of formula 1 is represented by the following
formula 3, 4, 5, or 6:
##STR00002##
[0022] wherein
[0023] A.sub.1, A.sub.2 and X.sub.1 to X.sub.16 are as defined in
formula 1.
[0024] In formula 1, A.sub.1 and A.sub.2 each independently
represent a substituted or unsubstituted (C6-C30)aryl group;
preferably, a substituted or unsubstituted (C6-C18)aryl group; more
preferably, a (C6-C18)aryl group which is unsubstituted or
substituted with a (C1-C6)alkyl group, a (C6-C12)aryl group, or a
tri(C6-C12)arylsilyl group; and even more preferably, phenyl,
biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl,
anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl,
perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl.
[0025] In formula 1, X.sub.1 to X.sub.16 each independently
represent hydrogen, deuterium, a halogen, a cyano group, a
substituted or unsubstituted (C1-C30)alkyl group, a substituted or
unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted
(C2-C30)alkynyl group, a substituted or unsubstituted
(C3-C30)cycloalkyl group, a substituted or unsubstituted
(C6-C60)aryl group, a substituted or unsubstituted 3- to
30-membered heteroaryl group, a substituted or unsubstituted
tri(C1-C30)alkylsilyl group, a substituted or unsubstituted
tri(C6-C30)arylsilyl group, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or
unsubstituted mono- or di-(C6-C30)arylamino group; or are linked
between adjacent substituents to form a substituted or
unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring whose carbon atom(s) ring may be replaced with at least one
hetero atom selected from nitrogen, oxygen and sulfur; preferably,
hydrogen, a substituted or unsubstituted (C6-C20)aryl group, a
substituted or unsubstituted tri(C6-C12)arylsilyl group, or a
substituted or unsubstituted 3- to 15-membered heteroaryl group;
and more preferably, hydrogen, a substituted or unsubstituted
(C6-C18)aryl group, an unsubstituted triphenylsilyl group, a
substituted or unsubstituted dibenzothiophene group, or a
substituted or unsubstituted dibenzofuran group.
[0026] The compound of formula 2 is represented by the following
formula 7, 8, or 9:
##STR00003##
[0027] wherein
[0028] V and W each independently represent a single bond,
NR.sub.15, CR.sub.16R.sub.17, S, or O, provided that both V and W
neither represent a single bond nor represent NR.sub.15;
[0029] A.sub.2 represents a substituted or unsubstituted
(C6-C30)aryl group and may be bonded to Xn or Xo;
[0030] L.sub.3 and L.sub.4 each independently represent a single
bond, or a substituted or unsubstituted (C6-C60)arylene group;
[0031] Xi represents hydrogen, deuterium, a halogen, a cyano group,
a substituted or unsubstituted (C1-C30)alkyl group, a substituted
or unsubstituted (C2-C30)alkenyl group, a substituted or
unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted
(C3-C30)cycloalkyl group, a substituted or unsubstituted
(C6-C60)aryl group, a substituted or unsubstituted 3- to
30-membered heteroaryl group, a substituted or unsubstituted
tri(C1-C30)alkylsilyl group, a substituted or unsubstituted
tri(C6-C30)arylsilyl group, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl group, or a substituted or
unsubstituted mono- or di-(C6-C30)arylamino group; or are linked
between adjacent substituents to form a substituted or
unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring whose carbon atom(s) ring may be replaced with at least one
hetero atom selected from nitrogen, oxygen and sulfur;
[0032] Xj to Xz each independently represent hydrogen, deuterium, a
halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl
group, a substituted or unsubstituted (C1-C30)alkyl group, a
substituted or unsubstituted (C3-C30)cycloalkyl group, a
substituted or unsubstituted (C3-C30)cycloalkenyl group, a
substituted or unsubstituted 3- to 7-membered heterocycloalkyl
group, a substituted or unsubstituted (C6-C60)aryl group, a
substituted or unsubstituted 3- to 30-membered heteroaryl group,
--NR.sub.5R.sub.6, or --SiR.sub.7R.sub.8R.sub.9; or are linked
between adjacent substituents to form a substituted or
unsubstituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring whose carbon atom(s) ring may be replaced with at least one
hetero atom selected from nitrogen, oxygen and sulfur;
[0033] Ma, La, Xa, Xb, and Xe to Xh are as defined in formula
2;
[0034] R.sub.5 to R.sub.9 each independently represent hydrogen,
deuterium, a halogen, a cyano group, a carboxyl group, a nitro
group, a hydroxyl group, a substituted or unsubstituted
(C1-C30)alkyl group, a substituted or unsubstituted
(C3-C30)cycloalkyl group, a substituted or unsubstituted
(C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to
7-membered heterocycloalkyl group, a substituted or unsubstituted
(C6-C60)aryl group, or a substituted or unsubstituted 3- to
30-membered heteroaryl group; or are linked between adjacent
substituents to form a substituted or unsubstituted mono- or
polycyclic, (C3-C30) alicyclic or aromatic ring whose carbon
atom(s) ring may be replaced with at least one hetero atom selected
from nitrogen, oxygen and sulfur; preferably, hydrogen, or a
substituted or unsubstituted (C6-C25)aryl group; more preferably,
hydrogen or an unsubstituted (C6-C18)aryl group; and specifically,
hydrogen, an unsubstituted phenyl group, a biphenyl group, or a
fluorenyl group;
[0035] R.sub.16 and R.sub.17 each independently represent hydrogen,
deuterium, a halogen, a cyano group, a carboxyl group, a nitro
group, a hydroxyl group, a substituted or unsubstituted
(C1-C30)alkyl group, a substituted or unsubstituted
(C3-C30)cycloalkyl group, a substituted or unsubstituted
(C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to
7-membered heterocycloalkyl group, a substituted or unsubstituted
(C6-C60)aryl group, or a substituted or unsubstituted 3- to
30-membered heteroaryl group; and
[0036] R.sub.15 represents hydrogen, deuterium, a halogen, a cyano
group, a carboxyl group, a nitro group, a hydroxyl group, a
substituted or unsubstituted (C1-C30)alkyl group, a substituted or
unsubstituted (C3-C30)cycloalkyl group, a substituted or
unsubstituted (C3-C30)cycloalkenyl group, a substituted or
unsubstituted 3- to 7-membered heterocycloalkyl group, a
substituted or unsubstituted (C6-C60)aryl group, or a substituted
or unsubstituted 3- to 30-membered heteroaryl group; preferably, a
substituted or unsubstituted (C6-C30)aryl group; and more
preferably, a substituted or unsubstituted phenyl group, an
unsubstituted biphenyl group, an unsubstituted naphthyl group, or a
substituted fluorenyl group.
[0037] In formula 2, La represents a single bond, or a substituted
or unsubstituted (C6-C30)arylene group; preferably, a single bond,
or a substituted or unsubstituted (C6-C12)arylene group; and more
preferably, a single bond, a (C6-C12)arylene group which is
unsubstituted or substituted with a tri(C6-C10)arylsilyl group or a
(C6-C12)aryl group.
[0038] Furthermore, La represents a single bond, or is represented
by one selected from the following formulas 10 to 19:
##STR00004## ##STR00005##
[0039] wherein
[0040] Xi to Xp each independently represent hydrogen, deuterium, a
halogen, a cyano group, a substituted or unsubstituted
(C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl
group, a substituted or unsubstituted (C2-C30)alkynyl group, a
substituted or unsubstituted (C3-C30)cycloalkyl group, a
substituted or unsubstituted (C6-C60)aryl group, a substituted or
unsubstituted 3- to 30-membered heteroaryl group, a substituted or
unsubstituted tri(C1-C30)alkylsilyl group, a substituted or
unsubstituted tri(C6-C30)arylsilyl group, a substituted or
unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, or a
substituted or unsubstituted mono- or di-(C6-C30)arylamino group;
or are linked between adjacent substituents to form a substituted
or unsubstituted mono- or polycyclic, (C3-C30) alicyclic or
aromatic ring whose carbon atom(s) ring may be replaced with at
least one hetero atom selected from nitrogen, oxygen and sulfur;
preferably, hydrogen, a cyano group, a substituted or unsubstituted
(C6-C15)aryl group, a substituted or unsubstituted 10- to
20-membered heteroaryl group, or a substituted or unsubstituted
tri(C6-C10)arylsilyl group; more preferably, hydrogen, a cyano
group, a (C6-C15)aryl group which is unsubstituted or substituted
with a tri(C6-C10)arylsilyl group, or a 10- to 20-membered
heteroaryl group which is unsubstituted or substituted with a
(C6-C15)aryl group.
[0041] In formula 2, Ma represents a substituted or unsubstituted
nitrogen-containing 5- to 11-membered heteroaryl group; preferably,
a substituted or unsubstituted nitrogen-containing 6- to
10-membered heteroaryl group; and more preferably, a
nitrogen-containing 6- to 10-membered heteroaryl group which is
substituted with a substituents(s) selected from the group
consisting of an unsubstituted (C6-C18)aryl group, a (C6-C12)aryl
group substituted with a cyano group, a (C6-C12)aryl group
substituted with a (C1-C6)alkyl group, a (C6-C12)aryl group
substituted with a tri(C6-C12)arylsilyl group, and a 6- to
15-membered heteroaryl group.
[0042] Furthermore, Ma represents a monocyclic-based heteroaryl
group selected from the group consisting of pyrrolyl, imidazolyl,
pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl,
pyrazinyl, pyrimidinyl, pyridazinyl, etc., or a fused ring-based
heteroaryl group selected from the group consisting of
benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl,
quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, naphthyridinyl,
quinoxalinyl, carbazolyl, phenanthridinyl, etc.; preferably,
triazinyl, pyrimidinyl, pyridyl, quinolyl, isoquinolyl,
quinazolinyl, naphthyridinyl, or quinoxalinyl.
[0043] Herein, "(C1-C30)alkyl(ene)" is meant to be a linear or
branched alkyl(ene) having 1 to 30 carbon atoms, in which the
number of carbon atoms is preferably 1 to 20, more preferably 1 to
10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl,
isobutyl, tert-butyl, etc. "(C2-C30)alkenyl" is meant to be a
linear or branched alkenyl having 2 to 30 carbon atoms, in which
the number of carbon atoms is preferably 2 to 20, more preferably 2
to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl,
2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. "(C2-C30)alkynyl" is
a linear or branched alkynyl having 2 to 30 carbon atoms, in which
the number of carbon atoms is preferably 2 to 20, more preferably 2
to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,
2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
"(C3-C30)cycloalkyl" is a mono- or polycyclic hydrocarbon having 3
to 30 carbon atoms, in which the number of carbon atoms is
preferably 3 to 20, more preferably 3 to 7, and includes
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "3- to
7-membered heterocycloalkyl" is a cycloalkyl having at least one
heteroatom selected from the group consisting of B, N, O, S,
P(.dbd.O), Si and P, preferably O, S and N, and 3 to 7, preferably
5 to 7 ring backbone atoms, and includes tetrahydrofuran,
pyrrolidine, thiolan, tetrahydropyran, etc. "(C6-C30)aryl(ene)" is
a monocyclic or fused ring derived from an aromatic hydrocarbon
having 6 to 30 carbon atoms, in which the number of carbon atoms is
preferably 6 to 20, more preferably 6 to 15, and includes phenyl,
biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl,
anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl,
perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. "3- to
30-membered heteroaryl(ene)" is an aryl group having at least one,
preferably 1 to 4 heteroatom selected from the group consisting of
B, N, O, S, P(.dbd.O), Si and P, and 3 to 30 ring backbone atoms;
is a monocyclic ring, or a fused ring condensed with at least one
benzene ring; has preferably 3 to 20, more preferably 3 to 15 ring
backbone atoms; may be partially saturated; may be one formed by
linking at least one heteroaryl or aryl group to a heteroaryl group
via a single bond(s); and includes a monocyclic ring-type
heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl,
pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl,
oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl,
tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl,
pyridazinyl, etc., and a fused ring-type heteroaryl including
benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl,
dibenzothiophenyl, benzoimidazolyl, benzothiazolyl,
benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl,
indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl,
cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl,
phenanthridinyl, benzodioxolyl, etc. "Nitrogen-containing 5- to
30-membered heteroaryl(ene) group" is an aryl(ene) group having at
least one heteroatom N and 5 to 30 ring backbone atoms. 5 to 20
ring backbone atoms and 1 to 4 heteroatom are preferable, and 5 to
15 ring backbone atoms are more preferable. It is a monocyclic
ring, or a fused ring condensed with at least one benzene ring; may
be partially saturated; may be one formed by linking at least one
heteroaryl or aryl group to a heteroaryl group via a single
bond(s); and includes a monocyclic ring-type heteroaryl including
pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl,
tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and
a fused ring-type heteroaryl including benzoimidazolyl, isoindolyl,
indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl,
cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl,
phenanthridinyl, etc. "Halogen" includes F, Cl, Br and I.
[0044] Herein, "substituted" in the expression "substituted or
unsubstituted" means that a hydrogen atom in a certain functional
group is replaced with another atom or group, i.e., a substituent.
Substituents of the substituted alkyl(ene) group, the substituted
alkenyl group, the substituted alkynyl group, the substituted
cycloalkyl group, the substituted aryl(ene) group, the substituted
heteroaryl(ene) group, the substituted trialkylsilyl group, the
substituted triarylsilyl group, the substituted dialkylarylsilyl
group, the substituted mono- or di-arylamino group, or the
substituted mono- or polycyclic, (C3-C30) alicyclic or aromatic
ring are each independently at least one selected from the group
consisting of deuterium; a halogen; a cyano group; a carboxyl
group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a
halo(C1-C30)alkyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl
group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a
(C3-C30)cycloalkyl group; a (C3-C30)cycloalkenyl group; a 3- to
7-membered heterocycloalkyl group; a (C6-C30)aryloxy group; a
(C6-C30)arylthio group; a 3- to 30-membered heteroaryl group which
is unsubstituted or substituted with a (C6-C30)aryl group; a
(C6-C30)aryl group which is unsubstituted or substituted with a
cyano group, a 3- to 30-membered heteroaryl group, or a
tri(C6-C30)arylsilyl group; a tri(C1-C30)alkylsilyl group; a
tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl
group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a
mono- or di(C1-C30)alkylamino group; a mono- or di(C6-C30)arylamino
group; a (C1-C30)alkyl(C6-C30)arylamino group; a
(C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a
(C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a
di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl
group; a (C6-C30)aryl(C1-C30)alkyl group; and a
(C1-C30)alkyl(C6-C30)aryl group. Preferably, the substituents are
each independently at least one selected from the group consisting
of a (C1-C6)alkyl group; a 5- to 15-membered heteroaryl group; a
(C6-C18)aryl group which is unsubstituted or substituted with a
cyano group or a tri(C6-C12)arylsilyl group; a tri(C6-C12)arylsilyl
group; and a (C1-C6)alkyl(C6-C12)aryl group.
[0045] The compound of formula 1 as a first host compound may be
selected from the group consisting of following compounds, but is
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## ##STR00037## ##STR00038## ##STR00039## ##STR00040##
##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045##
##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050##
##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055##
##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060##
##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065##
##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070##
##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075##
##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080##
##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085##
##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090##
##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095##
##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100##
##STR00101## ##STR00102## ##STR00103## ##STR00104##
[0046] The compound of formula 2 as a second host compound may be
selected from the group consisting of following compounds, but is
not limited thereto:
##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109##
##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114##
##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119##
##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124##
##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129##
##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134##
##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139##
##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144##
##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149##
##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154##
##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159##
##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164##
##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169##
##STR00170## ##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## ##STR00203## ##STR00204## ##STR00205##
##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210##
##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215##
##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220##
##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225##
##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230##
##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235##
##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240##
##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245##
##STR00246##
##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251##
##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256##
##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261##
##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266##
##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271##
##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276##
##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281##
##STR00282## ##STR00283##
##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288##
##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293##
##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298##
##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303##
##STR00304## ##STR00305## ##STR00306## ##STR00307##
[0047] The organic EL device according to the present invention may
comprise an anode, a cathode, and at least one organic layer
between the two electrodes, wherein the organic layer comprises a
light-emitting layer, the light-emitting layer comprises a host and
a phosphorescent dopant; the host consists of multi-component host
compounds; at least a first host compound of the multi-component
host compounds is represented by formula 1 which is a specific
bicarbazole derivative containing an aryl group, and a second host
compound is represented by formula 2 which is a specific carbazole
derivative including a nitrogen-containing heteroaryl group
[0048] The light-emitting layer means a layer emitting light and
may be a single layer or multi-layers consisting of two or more
layers. The doping concentration of dopant compounds to host
compounds in the light-emitting layer is preferably less than 20 wt
%.
[0049] The dopants included in the organic EL device of the present
invention are preferably one or more phosphorescent dopants. The
phosphorescent dopant material applied to the organic
electroluminescent device of the present invention is not
specifically limited, but preferably may be selected from complex
compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum
(Pt), more preferably ortho metallated complex compounds of iridium
(Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more
preferably ortho metallated iridium complex compounds.
[0050] The phosphorescent dopants may be selected from the group
consisting of the compounds represented by the following formulae
101 to 103:
##STR00308##
[0051] wherein
[0052] L is selected from the following structures:
##STR00309##
[0053] R.sub.100 represents hydrogen, or a substituted or
unsubstituted (C1-C30)alkyl group; R.sub.101 to R.sub.109 and
R.sub.111 to R.sub.123 each independently represent hydrogen,
deuterium, a halogen; a (C1-C30)alkyl group unsubstituted or
substituted with halogen(s); a cyano group, a substituted or
unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted
(C6-C30)aryl group, or a substituted or unsubstituted
(C3-C30)cycloalkyl group; R.sub.120 to R.sub.123 are linked to an
adjacent substituent(s) to form a substituted or unsubstituted
mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, for
example, quinoline; R.sub.124 to R.sub.127 each independently
represent hydrogen, deuterium, a halogen, a substituted or
unsubstituted (C1-C30)alkyl group, or a substituted or
unsubstituted (C6-C30)aryl group; when R.sub.124 to R.sub.127 are
aryl groups, they are linked to an adjacent substituent(s) to form
a substituted or unsubstituted mono- or polycyclic, (C3-C30)
alicyclic or aromatic ring, or a heteroaromatic ring, for example,
fluorene, dibenzothiophene, or dibenzofuran; R.sub.201 to R.sub.211
each independently represent hydrogen, deuterium, a halogen, a
(C1-C30)alkyl group unsubstituted or substituted with halogen(s),
or a substituted or unsubstituted (C6-C30)aryl group; R.sub.208 to
R.sub.211 may be linked to an adjacent substituent(s) to form a
substituted or unsubstituted mono- or polycyclic, (C3-C30)
alicyclic or aromatic ring, or a heteroaromatic ring, for example,
fluorene, dibenzothiophene, or dibenzofuran; r and s each
independently represent an integer of 1 to 3; where r or s is an
integer of 2 or more, each of R.sub.100 may be the same or
different; and e represents an integer of 1 to 3.
[0054] The phosphorescent dopant material includes the
following:
##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314##
##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319##
##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324##
##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329##
##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334##
##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339##
##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344##
##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349##
##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354##
##STR00355## ##STR00356##
[0055] The organic EL device of the present invention may further
include at least one compound selected from the group consisting of
arylamine-based compounds and styrylarylamine-based compounds in
the organic layer.
[0056] In the organic EL device of the present invention, the
organic layer may further comprise at least one metal selected from
the group consisting of metals of Group 1, metals of Group 2,
transition metals of the 4th period, transition metals of the 5th
period, lanthanides, and organic metals of d-transition elements of
the Periodic Table, or at least one complex compound comprising the
metal.
[0057] Preferably, in the organic electroluminescent device of the
present invention, at least one layer (hereinafter, "a surface
layer") selected from a chalcogenide layer, a metal halide layer
and a metal oxide layer may be placed on an inner surface(s) of one
or both electrode(s). Specifically, it is preferred that a
chalcogenide (including oxides) layer of silicon or aluminum is
placed on an anode surface of a light-emitting medium layer, and a
metal halide layer or metal oxide layer is placed on a cathode
surface of an electroluminescent medium layer. The surface layer
provides operating stability for the organic electroluminescent
device. Preferably, the chalcogenide includes
SiO.sub.X(1.ltoreq.X.ltoreq.2), AlO.sub.X(1.ltoreq.X.ltoreq.5),
SiON, SiAlON, etc.; the metal halide includes LiF, MgF.sub.2,
CaF.sub.2, a rare earth metal fluoride, etc.; and the metal oxide
includes Cs.sub.2O, Li.sub.2O, MgO, SrO, BaO, CaO, etc.
[0058] A hole injection layer, a hole transport layer, an electron
blocking layer, or their combinations can be used between an anode
and a light-emitting layer. The hole injection layer may be
multi-layers in order to lower a hole injection barrier (or hole
injection voltage) from an anode to a hole transport layer or an
electron blocking layer, wherein each of the multi-layers
simultaneously uses two compounds. The hole transport layer or the
electron blocking layer may also be multi-layers.
[0059] An electron buffer layer, a hole blocking layer, an electron
transport layer, an electron injection layer, or their combinations
can be used between a light-emitting layer and a cathode. The
electron buffer layer may be multi-layers in order to control the
injection of an electron and improve interface properties between
the light-emitting layer and the electron injection layer, wherein
each of the multi-layers simultaneously uses two compounds. The
hole blocking layer or the electron transport layer may also be
multi-layers, wherein each of the multi-layers may use a
multi-component of compounds.
[0060] Preferably, in the organic electroluminescent device of the
present invention, a mixed region of an electron transport compound
and a reductive dopant, or a mixed region of a hole transport
compound and an oxidative dopant may be placed on at least one
surface of a pair of electrodes. In this case, the electron
transport compound is reduced to an anion, and thus it becomes
easier to inject and transport electrons from the mixed region to a
light-emitting medium. Further, the hole transport compound is
oxidized to a cation, and thus it becomes easier to inject and
transport holes from the mixed region to a light-emitting medium.
Preferably, the oxidative dopant includes various Lewis acids and
acceptor compounds; and the reductive dopant includes alkali
metals, alkali metal compounds, alkaline earth metals, rare-earth
metals, and mixtures thereof. A reductive dopant layer may be
employed as a charge-generating layer to prepare an organic
electroluminescent device having two or more light-emitting layers
and emitting white light.
[0061] In order to form each layer constituting the organic
electroluminescent device of the present invention, dry
film-forming methods, such as vacuum deposition, sputtering,
plasma, ion plating methods, etc., or wet film-forming methods,
such as spin coating, dip coating, flow coating methods, etc., can
be used. When forming a layer by using a first host and a second
host according to the present invention, co-deposition or
mixed-deposition may be used.
[0062] When using a wet film-forming method, a thin film is formed
by dissolving or dispersing the material constituting each layer in
suitable solvents, such as ethanol, chloroform, tetrahydrofuran,
dioxane, etc. The solvents are not specifically limited as long as
the material constituting each layer is soluble or dispersible in
the solvents, which do not cause any problems in forming a
layer.
[0063] Furthermore, a display device or a light device can be
produced by using the organic EL device of the present
invention.
[0064] Hereinafter, the preparation methods of devices by using
host compounds and dopant compounds of the present invention will
be explained in detail with reference to the following
examples:
Device Example 1-1: Production of an OLED Device by Co-Deposition
of the First Host Compound and the Second Host Compound According
to the Present Invention as a Host
[0065] An OLED device comprising the organic electroluminescent
compound of the present invention was produced as follows: A
transparent electrode indium tin oxide (ITO) thin film (10
.OMEGA./sq) on a glass substrate for an OLED device (Samsung
Corning, Republic of Korea) was subjected to an ultrasonic washing
with trichloroethylene, acetone, ethanol, and distilled water,
sequentially, and was then stored in isopropanol. Next, the ITO
substrate was mounted on a substrate holder of a vacuum vapor
depositing apparatus.
N.sup.4,N.sup.4'-diphenyl-N.sup.4,N.sup.4'-bis(9-phenyl-9H-carbazole-3-yl-
)-[1,1'-biphenyl]-4,4'-diamine as HI-1 was introduced into a cell
of the vacuum vapor depositing apparatus, and the pressure in the
chamber of the apparatus was then controlled to 10.sup.-6 torr.
Thereafter, an electric current was applied to the cell to
evaporate the introduced material, thereby forming a hole injection
layer 1 having a thickness of 80 nm on the ITO substrate.
1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile as HI-2 was then
introduced into another cell of the vacuum vapor depositing
apparatus, and an electric current was applied to the cell to
evaporate the introduced material, thereby forming a hole injection
layer 2 having a thickness of 5 nm on hole injection layer 1.
N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)ph-
enyl)-9H-fluorene-2-amine as HT-1 was introduced into one cell of
the vacuum vapor depositing apparatus. Thereafter, an electric
current was applied to the cell to evaporate the introduced
material, thereby forming a hole transport layer 1 having a
thickness of 10 nm on hole injection layer 2.
N,N-di([1,1'-biphenyl]-4-yl)-4'-(9H-carbazole-9-yl)-[1,1'-biphen-
yl]-4-amine as HT-2 was then introduced into another cell of the
vacuum vapor depositing apparatus, and an electric current was
applied to the cell to evaporate the introduced material, thereby
forming a hole transport layer 2 having a thickness of 60 nm on
hole transport layer 1. Thereafter, compounds H1-1 and H2-2 as
hosts were respectively introduced into two cells of the vacuum
vapor depositing apparatus and compound D-96 as a dopant was
introduced into another cell. The two host materials were
evaporated at the same rates of 1:1, and the dopant was evaporated
at a different rate and deposited in a doping amount of 3 wt %,
based on the total weight of the host and dopant, to form a
light-emitting layer having a thickness of 40 nm on the hole
transport layer. Next,
2,4-bis(9,9-dimethyl-9H-fluorene-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazin-
e as ET-1 and lithium quinolate as EI-1 were evaporated at the same
rates of 1:1 on another two cells to form an electron transport
layer having a thickness of 30 nm on the light-emitting layer.
After depositing lithium quinolate of EI-1 having a thickness of 2
nm as an electron injection layer on the electron transport layer,
an Al cathode having a thickness of 80 nm was then deposited by
another vacuum vapor deposition apparatus on the electron injection
layer. Thus, an OLED device was produced.
[0066] The produced OLED device showed the driving voltage at a
luminance of 1,000 nit, luminescent efficiency, CIE color
coordinate, and the lifespan taken to be reduced from 100% to 90%
of the constant current at a luminance of 5,000 nit as provided in
Table 1 below.
##STR00357## ##STR00358##
Comparative Example 1-1: Production of an OLED Device by Using Only
the Second Host Compound According to the Present Invention as a
Host
[0067] An OLED device was produced in the same manner as in Device
Example 1-1, except that only the second host compound was used as
a host in a light-emitting layer.
[0068] The luminescent properties of the OLED devices produced in
Device Example 1-1 and Comparative Example 1-1 are provided in
Table 1 below.
TABLE-US-00001 TABLE 1 Hole Color Transport Efficiency Coordinate
T90 Layer Host Dopant Voltage (V) (cd/A) (x,y) lifespan (hr) Device
HT-1/HT-2 H1-1:H2-2 D-96 4.3 25.5 0.663, 360 Example 1-1 0.336
Comparative HT-1/HT-2 H2-2 D-96 4.1 28.2 0.662, 100 Example 1-1
0.337
Device Examples 2-1 to 2-13: Production of an OLED Device by
Co-Deposition of the First Host Compound and the Second Host
Compound According to the Present Invention as a Host
[0069] An OLED device was produced in the same manner as in Device
Example 1-1, except that hole injection layer 2 has a thickness of
3 nm, hole transport layer 1 has a thickness of 40 nm, hole
transport layer 2 is not present, D-25 as a dopant was deposited in
a doping amount on 15 wt % in a light-emitting layer, the electron
transport layer having a thickness of 35 nm was deposited via the
evaporation rate of 4:6, the combinations of the first host
compound and the second host compound used as hosts in a
light-emitting layer are based on Device Examples 2-1 to 2-13 as
provided in Table 2 below, and the lifespan taken to be reduced
from 100% to 90% of the constant current at a luminance of 15,000
nit as provided in Table 2 below.
Device Examples 2-14 to 2-18: Production of an OLED Device by
Co-Deposition of the First Host Compound and the Second Host
Compound According to the Present Invention as a Host
[0070] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-13, except that hole injection layer 2 has a
thickness of 3 nm, hole transport layer 1 has a thickness of 40 nm,
hole transport layer 2 is not present, D-1 as a dopant was used in
a light-emitting layer, the electron transport layer having a
thickness of 35 nm was deposited via the evaporation rate of 4:6,
the combinations of the first host compound and the second host
compound used as hosts in a light-emitting layer are based on
Device Examples 2-14 to 2-18 as provided in Table 2 below, and the
lifespan taken to be reduced from 100% to 90% of the constant
current at a luminance of 15,000 nit as provided in Table 2
below.
Device Examples 3-1 to 3-8: Production of an OLED Device by
Co-Deposition of the First Host Compound and the Second Host
Compound According to the Present Invention as a Host
[0071] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-13, except that hole transport layer 1 has a
thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness
of 30 nm, D-136 as a dopant was used in a light-emitting layer, and
the combinations of the first host compound and the second host
compound used as hosts in a light-emitting layer are based on
Device Examples 3-1 to 3-8 as provided in Table 2 below.
Device Example 3-9: Production of an OLED Device by Co-Deposition
of the First Host Compound and the Second Host Compound According
to the Present Invention as a Host
[0072] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-13, except that hole transport layer 1 has a
thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness
of 30 nm, D-164 as a dopant was used in a light-emitting layer, and
the combinations of the first host compound and the second host
compound used as hosts in a light-emitting layer are based on
Device Example 3-9 as provided in Table 2 below.
Device Examples 3-10 to 3-12: Production of an OLED Device by
Co-Deposition of the First Host Compound and the Second Host
Compound According to the Present Invention as a Host
[0073] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-13, except that hole transport layer 1 has a
thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness
of 30 nm, D-168 as a dopant was used in a light-emitting layer, and
the combinations of the first host compound and the second host
compound used as hosts in a light-emitting layer are based on
Device Examples 3-10 to 3-12 as provided in Table 2 below.
Device Example 3-13: Production of an OLED Device by Co-Deposition
of the First Host Compound and the Second Host Compound According
to the Present Invention as a Host
[0074] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-13, except that hole transport layer 1 has a
thickness of 10 nm, hole transport layer 2 of HT-3 has a thickness
of 30 nm, D-180 as a dopant was used in a light-emitting layer, and
the combinations of the first host compound and the second host
compound used as hosts in a light-emitting layer are based on
Device Example 3-13 as provided in Table 2 below.
Comparative Examples 2-1 to 2-3: Production of an OLED Device by
Using Only the First Host Compound According to the Present
Invention as a Host
[0075] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-13, except that the first host compound used as
hosts in a light-emitting layer is based on Comparative Examples
2-1 to 2-3 as provided in Table 2 below.
Comparative Examples 3-1 to 3-9: Production of an OLED Device by
Using Only the Second Host Compound According to the Present
Invention as a Host
[0076] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-13, except that the second host compound used as
hosts in a light-emitting layer is based on Comparative Examples
3-1 to 3-9 as provided in Table 2 below.
Comparative Example 4-1: Production of an OLED Device by Using Only
the Second Host Compound According to the Present Invention as a
Host
[0077] An OLED device was produced in the same manner as in Device
Examples 3-1 to 3-8, except that the second host compound used as
hosts in a light-emitting layer is based on Comparative Example 4-1
as provided in Table 2 below.
[0078] The luminescent properties of the OLED devices produced in
the above Device Examples and Comparative Examples are provided in
Table 2 below.
TABLE-US-00002 TABLE 2 Hole Color T90 Transport Voltage Efficiency
Coordinate lifespan Layer Host Dopant [V] [cd/A] (x,y) [hr] Device
HT-1 H1-1:H2-25 D-25 3.3 43.2 0.297, 0.660 100 Example 2-1 Device
HT-1 H1-1:H2-31 D-25 3 58.8 0.303, 0.657 143 Example 2-2 Device
HT-1 H1-1:H2-48 D-25 2.8 55.3 0.302, 0.657 124 Example 2-3 Device
HT-1 H1-1:H2-34 D-25 3 55.7 0.302, 0.657 127 Example 2-4 Device
HT-1 H1-11:H2-31 D-25 2.9 56.9 0.306, 0.656 147 Example 2-5 Device
HT-1 H1-12:H2-31 D-25 2.9 54.5 0.304, 0.657 206 Example 2-6 Device
HT-1 H1-14:H2-31 D-25 3.1 49.1 0.306, 0.655 124 Example 2-7 Device
HT-1 H1-4:H2-31 D-25 2.9 55.2 0.300, 0.657 131 Example 2-8 Device
HT-1 H1-35:H2-31 D-25 2.9 55.6 0.303, 0.656 161 Example 2-9 Device
HT-1 H1-1:H2-101 D-25 3 55.6 0.303, 0.656 124 Example 2-10 Device
HT-1 H1-9:H2-31 D-25 2.9 56 0.301, 0.657 203 Example 2-11 Device
HT-1 H1-2:H2-31 D-25 2.8 54.9 0.307, 0.656 116 Example 2-12 Device
HT-1 H1-34:H2-31 D-25 3 52.5 0.303, 0.657 160 Example 2-13 Device
HT-1 H1-1:H2-31 D-1 2.8 57.8 0.315, 0.658 254 Example 2-14 Device
HT-1 H1-1:H2-48 D-1 2.8 60.2 0.316, 0.659 240 Example 2-15 Device
HT-1 H1-11:H2-31 D-1 2.8 52.4 0.317, 0.658 274 Example 2-16 Device
HT-1 H1-11:H2-48 D-1 2.7 54.3 0.316, 0.659 272 Example 2-17 Device
HT-1 H1-11:H2-87 D-1 2.9 51.9 0.319, 0.655 240 Example 2-18 Device
HT-1/HT-3 H1-1:H2-30 D-136 3.3 63.9 0.324, 0.660 240 Example 3-1
Device HT-1/HT-3 H1-1:H2-31 D-136 3.2 71.2 0.326, 0.659 265 Example
3-2 Device HT-1/HT-3 H1-1:H2-48 D-136 3.1 68 0.325, 0.659 265
Example 3-3 Device HT-1/HT-3 H1-1:H2-87 D-136 3.3 67.4 0.327, 0.658
290 Example 3-4 Device HT-1/HT-3 H1-11:H2-31 D-136 3.1 69.2 0.327,
0.658 292 Example 3-5 Device HT-1/HT-3 H1-11:H2-48 D-136 3.2 64
0.326, 0.658 322 Example 3-6 Device HT-1/HT-3 H1-11:H2-87 D-136 3.1
65.2 0.327, 0.657 367 Example 3-7 Device HT-1/HT-3 H1-35:H2-125
D-136 3.1 65.2 0.330, 0.655 408 Example 3-8 Device HT-1/HT-3
H1-35:H2-31 D-164 3.2 61.5 0.316, 0.656 241 Example 3-9 Device
HT-1/HT-3 H1-1:H2-31 D-168 3.2 62.1 0.281, 0.665 148 Example 3-10
Device HT-1/HT-3 H1-35:H2-31 D-168 3.2 59.4 0.278, 0.668 162
Example 3-11 Device HT-1/HT-3 H1-12:H2-125 D-168 3.1 56.6 0.288,
0.665 164 Example 3-12 Device HT-1/HT-3 H1-12:H2-125 D-180 3.1 49.7
0.291, 0.664 240 Example 3-13 Comparative HT-1 H1-12 D-25 5.9 3.1
0.299, 0.656 x Example 2-1 Comparative HT-1 H1-4 D-25 6.7 3 0.289,
0.658 x Example 2-2 Comparative HT-1 H1-35 D-25 6.6 3.9 0.395,
0.658 x Example 2-3 Comparative HT-1 H2-25 D-25 3.1 54.2 0.308,
0.655 45 Example 3-1 Comparative HT-1 H2-31 D-25 2.9 42.8 0.314,
0.652 39 Example 3-2 Comparative HT-1 H2-48 D-25 2.6 49.6 0.314,
0.652 67 Example 3-3 Comparative HT-1 H2-101 D-25 2.8 50.3 0.315,
0.651 24 Example 3-4 Comparative HT-1 H2-34 D-25 2.7 49.2 0.312,
0.652 38 Example 3-5 Comparative HT-1 H2-30 D-25 2.8 55.3 0.314,
0.652 70 Example 3-6 Comparative HT-1 H2-31 D-1 2.9 33.5 0.323,
0.653 130 Example 3-7 Comparative HT-1 H2-48 D-1 2.6 41.2 0.325,
0.653 124 Example 3-8 Comparative HT-1 H2-87 D-1 2.8 37.9 0.323,
0.653 146 Example 3-9 Comparative HT-1/HT-3 H2-125 D-136 3.0 64.9
0.337, 0.649 124 Example 4-1
Device Examples 4-1 to 4-7: Production of an OLED Device by
Co-Deposition of the First Host Compound and the Second Host
Compound According to the Present Invention as a Host
[0079] An OLED device was produced in the same manner as in Device
Example 1-1, except that HT-4 was used as a hole transport layer 2,
the combinations of the first host compound and the second host
compound used as hosts in a light-emitting layer are based on
Device Examples 4-1 to 4-7 as provided in Table 3 below, and the
lifespan taken to be reduced from 100% to 95% of the constant
current at a luminance of 5,000 nit as provided in Table 3
below.
##STR00359##
Comparative Examples 5-1 and 5-2: Production of an OLED Device by
Using Only the Second Host Compound According to the Present
Invention as a Host
[0080] An OLED device was produced in the same manner as in Device
Examples 4-1 to 4-7, except that the second host compound used as
hosts in a light-emitting layer is based on Comparative Examples
5-1 and 5-2 as provided in Table 3 below.
[0081] The luminescent properties of the OLED devices produced in
Device Examples 4-1 to 4-7, and Comparative Examples 5-1 and 5-2
are provided in Table 3 below.
TABLE-US-00003 TABLE 3 Hole Color T95 Transport Voltage Efficiency
Coordinate lifespan Layer Host Dopant [V] [cd/A] (x,y) [hr] Device
HT-1/HT-4 H1-287:H2-496 D-96 3.8 30.8 0.667, 0.333 310 Example 4-1
Device HT-1/HT-4 H1-12:H2-504 D-96 3.5 30.7 0.667, 0.333 390
Example 4-2 Device HT-1/HT-4 H1-9:H2-496 D-96 3.9 31.1 0.665, 0.335
130 Example 4-3 Device HT-1/HT-4 H1-35:H2-496 D-96 3.8 31.1 0.665,
0.334 200 Example 4-4 Device HT-1/HT-4 H1-287:H2-504 D-96 3.7 31.3
0.666, 0.333 200 Example 4-5 Device HT-1/HT-4 H1-282:H2-504 D-96
3.7 31.4 0.666, 0.334 120 Example 4-6 Device HT-1/HT-4 H1-12:H2-496
D-96 3.6 29.2 0.667, 0.333 150 Example 4-7 Comparative HT-1/HT-4
H2-496 D-96 3.7 31.0 0.665, 0.334 90 Example 5-1 Comparative
HT-1/HT-4 H2-504 D-96 3.7 31 0.667, 0.333 70 Example 5-2
Device Examples 5-1 and 5-2: Production of an OLED Device by
Co-Deposition of the First Host Compound and the Second Host
Compound According to the Present Invention as a Host
[0082] An OLED device was produced in the same manner as in Device
Examples 3-1 to 3-11, except that D-134 was used as a dopant in a
light-emitting layer, the combinations of the first host compound
and the second host compound used as hosts in a light-emitting
layer are based on Device Examples 5-1 and 5-2 as provided in Table
4 below, and the lifespan taken to be reduced from 100% to 97% of
the constant current at a luminance of 15,000 nit as provided in
Table 4 below.
Comparative Examples 6-1 and 6-2: Production of an OLED Device by
Using Only the First Host Compound According to the Present
Invention as a Host
[0083] An OLED device was produced in the same manner as in Device
Examples 5-1 and 5-2, except that the first host compound used as
hosts in a light-emitting layer is based on Comparative Examples
6-1 and 6-2 as provided in Table 4 below.
Comparative Example 7-1: Production of an OLED Device by Using Only
the Second Host Compound According to the Present Invention as a
Host
[0084] An OLED device was produced in the same manner as in Device
Examples 5-1 and 5-2, except that the second host compound used as
hosts in a light-emitting layer is based on Comparative Example 7-1
as provided in Table 4 below.
[0085] The luminescent properties of the OLED devices produced in
Device Examples 5-1 and 5-2, Comparative Examples 6-1 and 6-2, and
Comparative Example 7-1 are provided in Table 4 below.
TABLE-US-00004 TABLE 4 Hole Color T97 Transport Voltage Efficiency
Coordinate lifespan Layer Host Dopant [V] [cd/A] (x,y) [hr] Device
HT-1/HT-3 H1-12:H2-660 D-134 3.1 63.2 0.313, 0.665 39 Example 5-1
Device HT-1/HT-3 H1-35:H2-660 D-134 3.2 64.8 0.312, 0.665 56
Example 5-2 Comparative HT-1/HT-3 H1-12 D-134 6.4 2.9 0.305, 0.660
x Example 6-1 Comparative HT-1/HT-3 H1-35 D-134 7.2 3.5 0.302,
0.664 x Example 6-2 Comparative HT-1/HT-3 H2-660 D-134 3.0 55.4
0.321, 0.659 5 Example 7-1
[0086] The organic electroluminescent device of the present
invention provides longer lifespan compared with conventional
devices by comprising a light-emitting layer containing a host and
a phosphorescent dopant, wherein the host consists of
multi-component host compounds, at least a first host compound of
the multi-component host compounds has a specific bicarbazole
derivative containing an aryl group, and a second host compound has
a specific carbazole derivative including a nitrogen-containing
heteroaryl group.
* * * * *