U.S. patent application number 15/301975 was filed with the patent office on 2017-05-04 for multi-component host material and an organic electroluminescence 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, Ji-Song Jun, Chi-Sik Kim, Nam-Kyun Kim, Young-Kwang Kim, Kyung-Joo Lee, Seon-Woo Lee, Su-Hyun Lee, Kyoung-Jin Park, Jae-Hoon Shim.
Application Number | 20170125699 15/301975 |
Document ID | / |
Family ID | 53027471 |
Filed Date | 2017-05-04 |
United States Patent
Application |
20170125699 |
Kind Code |
A1 |
Ahn; Hee-Choon ; et
al. |
May 4, 2017 |
MULTI-COMPONENT HOST MATERIAL AND AN ORGANIC ELECTROLUMINESCENCE
DEVICE COMPRISING THE SAME
Abstract
The present invention relates to a multi-component host material
and an organic electroluminescent device comprising the same. By
comprising a specific combination of the multi-component host
compounds, the organic electroluminescent device according to the
present invention can provide high luminous efficiency and
excellent lifespan characteristics.
Inventors: |
Ahn; Hee-Choon; (Seoul,
KR) ; Kim; Young-Kwang; (Hwaseong, KR) ; Lee;
Su-Hyun; (Suwon, KR) ; Jun; Ji-Song;
(Hwaseong, KR) ; Lee; Seon-Woo; (Osan, KR)
; Kim; Chi-Sik; (Hwaseong, KR) ; Park;
Kyoung-Jin; (Seongnam, KR) ; Kim; Nam-Kyun;
(Yongin, KR) ; Choi; Kyung-Hoon; (Hwaseong,
KR) ; Shim; Jae-Hoon; (Seoul, KR) ; Cho;
Young-Jun; (Seongnam, KR) ; Lee; Kyung-Joo;
(Seoul, KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Rohm and Haas Electronic Materials Korea Ltd. |
Cheonan |
|
KR |
|
|
Family ID: |
53027471 |
Appl. No.: |
15/301975 |
Filed: |
April 17, 2015 |
PCT Filed: |
April 17, 2015 |
PCT NO: |
PCT/KR2015/003890 |
371 Date: |
October 5, 2016 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07D 401/14 20130101;
H01L 51/0071 20130101; C09K 2211/185 20130101; H01L 2251/5384
20130101; C07F 15/0033 20130101; H01L 51/0052 20130101; C07D 401/10
20130101; C09K 11/025 20130101; C09K 2211/1029 20130101; C07D
495/04 20130101; H01L 51/0074 20130101; H01L 51/0061 20130101; C07D
491/04 20130101; C09K 11/06 20130101; C09K 2211/1007 20130101; H01L
51/0094 20130101; C07D 209/86 20130101; C07D 401/04 20130101; H01L
51/0072 20130101; H01L 51/5064 20130101; C07D 405/14 20130101; H01L
51/0067 20130101; C07D 209/88 20130101; C09K 2211/1088 20130101;
H01L 51/0073 20130101; H01L 51/0085 20130101; C07D 487/04 20130101;
H01L 51/5016 20130101; C07D 409/14 20130101 |
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 18, 2014 |
KR |
10-2014-0046857 |
Jul 11, 2014 |
KR |
10-2014-0087769 |
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, and a second host compound
is represented by the following formula 2. ##STR00280## wherein
A.sub.1 and A.sub.2 each independently represent a substituted or
unsubstituted (C6-C30)aryl; L.sub.1 represents a substituted or
unsubstituted (C6-C30)arylene; X.sub.1 to X.sub.16 each
independently represent hydrogen, deuterium, a halogen, a cyano, a
substituted or unsubstituted (C1-C30)alkyl, a substituted or
unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted
(C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl,
a substituted or unsubstituted (C6-C60)aryl, a substituted or
unsubstituted (3- to 30-membered)heteroaryl, a substituted or
unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted
tri(C6-C30)arylsilyl, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted
(C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted
mono- or di-(C6-C30)arylamino; or are linked to an adjacent
substituent(s) 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; ##STR00281## wherein Ma represents a
substituted or unsubstituted nitrogen-containing (5- to
11-membered)heteroaryl; La represents a single bond, or a
substituted or unsubstituted (C6-C30)arylene; Xa to Xh each
independently represent hydrogen, deuterium, a halogen, a cyano, a
substituted or unsubstituted (C1-C30)alkyl, a substituted or
unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted
(C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl,
a substituted or unsubstituted (C6-C60)aryl, a substituted or
unsubstituted (3- to 30-membered)heteroaryl, a substituted or
unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted
tri(C6-C30)arylsilyl, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted
mono- or di-(C6-C30)arylamino; or are linked to an adjacent
substituent(s) 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; and the heteroaryl 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 in formula 1, A.sub.1 and A.sub.2 each independently are
selected from the group consisting of phenyl, biphenyl, terphenyl,
naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl,
triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, and
fluoranthenyl.
3. The organic electroluminescent device according to claim 1,
wherein in formula 1, L.sub.1 is represented by one of the
following formulae 7 to 19: ##STR00282## ##STR00283## ##STR00284##
wherein Xi to Xp each independently represent hydrogen, deuterium,
a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a
substituted or unsubstituted (C2-C30)alkenyl, a substituted or
unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted
(C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a
substituted or unsubstituted (3- to 30-membered)heteroaryl, a
substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted
or unsubstituted tri(C6-C30)arylsilyl, a substituted or
unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or
unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or
unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an
adjacent substituent(s) 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.
4. The organic electroluminescent device according to claim 1,
wherein in formula 2, Ma represents a monocyclic heteroaryl
selected from the group consisting of pyrrolyl, imidazolyl,
pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl,
pyrazinyl, pyrimidinyl, and pyridazinyl, or a fused heteroaryl
selected from the group consisting of benzoimidazolyl, isoindolyl,
indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl,
cinnolinyl, quinazolinyl, naphthyridinyl, and quinoxalinyl.
5. The organic electroluminescent device according to claim 1,
wherein in formula 2, La is a single bond, or represented by one of
the following formulae 7 to 19: ##STR00285## ##STR00286##
##STR00287## wherein Xi to Xp each independently represent
hydrogen, deuterium, a halogen, a cyano, a substituted or
unsubstituted (C1-C30)alkyl, a substituted or unsubstituted
(C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a
substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or
unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to
30-membered)heteroaryl, a substituted or unsubstituted
tri(C1-C30)alkylsilyl, a substituted or unsubstituted
tri(C6-C30)arylsilyl, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted
(C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted
mono- or di-(C6-C30)arylamino; or are linked to an adjacent
substituent(s) 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.
6. The organic electroluminescent device according to claim 1,
wherein in formula 2, Xa to Xh each independently represent
hydrogen; a cyano; a (C6-C15)aryl unsubstituted or substituted with
a tri(C6-C10)arylsilyl; a (10- to 20-membered)heteroaryl
unsubstituted or substituted with a (C6-C12)aryl or a
cyano(C6-C12)aryl; or an unsubstituted tri(C6-C10)arylsilyl; or are
linked to an adjacent substituent(s) to form a substituted or
unsubstituted benzene, a substituted or unsubstituted indole, a
substituted or unsubstituted benzoindole, a substituted or
unsubstituted indene, a substituted or unsubstituted benzofuran, or
a substituted or unsubstituted benzothiophene.
7. The organic electroluminescent device according to claim 1,
wherein in formula 1, a triarylsilyl as X.sub.1 to X.sub.16 is a
triphenylsilyl.
8. The organic electroluminescent device according to claim 1,
wherein the compound represented by formula 1 is selected from the
group consisting of: ##STR00288## ##STR00289## ##STR00290##
##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295##
##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300##
##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305##
##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310##
##STR00311## ##STR00312## ##STR00313## ##STR00314##
##STR00315##
9. The organic electroluminescent device according to claim 1,
wherein the compound represented by formula 2 is selected from the
group consisting of: ##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## ##STR00357## ##STR00358##
##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363##
##STR00364## ##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##
##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##
Description
TECHNICAL FIELD
[0001] The present invention relates to a multi-component host
material and an organic electroluminescence device comprising the
same.
BACKGROUND ART
[0002] An electroluminescence device (EL device) is a
self-light-emitting device which has advantages in that it provides
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 [Appl.
Phys. Lett. 51, 913, 1987].
[0003] An organic EL device (OLED) is a device changing electronic
energy to light by applying electricity to an organic
electroluminescent material, and generally has a structure
comprising an anode, a cathode, and an organic layer between the
anode and the cathode. The organic layer of an organic EL device
may be comprised of a hole injection layer, a hole transport layer,
an electron blocking layer, a light-emitting layer (which comprises
host and dopant materials), an electron buffer layer, a hole
blocking layer, an electron transport layer, an electron injection
layer, etc., and the materials used for the organic layer are
categorized by their functions in hole injection material, hole
transport material, electron blocking material, light-emitting
material, electron buffer material, hole blocking material,
electron transport material, electron injection material, etc. In
the organic EL device, due to an application of a voltage, holes
are injected from the anode to the light-emitting layer, electrons
are injected from the cathode to the light-emitting layer, and
excitons of high energies are formed by a recombination of the
holes and the electrons. By this energy, luminescent organic
compounds reach an excited state, and light emission occurs by
emitting light from energy due to the excited state of the
luminescent organic compounds returning to a ground state.
[0004] The most important factor determining luminous efficiency in
an organic EL device is the light-emitting material. A
light-emitting material must have high quantum efficiency, high
electron and hole mobility, and the formed light-emitting material
layer must be uniform and stable. Light-emitting materials are
categorized into blue, green, and red light-emitting materials
dependent on the color of the light emission, additionally yellow
or orange light-emitting materials. In addition, Light-emitting
materials can also be categorized into host and dopant materials
according to their functions. Recently, the development of an
organic EL device providing high efficiency and long lifespan is an
urgent issue. In particular, considering EL characteristic
requirements for a middle or large-sized panel of OLED, materials
showing better characteristics than conventional ones must be
urgently developed. The host material which acts as a solvent in a
solid state and transfers energy needs to have high purity and a
molecular weight appropriate for vacuum deposition. Furthermore,
the host material needs to have high glass transition temperature
and high thermal degradation temperature to achieve thermal
stability, high electro-chemical stability to achieve long
lifespan, ease of forming amorphous thin film, good adhesion to
materials of adjacent layers, and non-migration to other
layers.
[0005] A light-emitting material can be used as a combination of a
host and a dopant to improve color purity, luminous efficiency, and
stability. Generally, an EL device having excellent characteristics
has a structure comprising a light-emitting layer formed by doping
a dopant to a host. Since host materials greatly influence the
efficiency and lifespan of the EL device when using a dopant/host
material system as a light emitting material, their selection is
important.
[0006] International Publication Nos. WO 2013/168688 A1 and WO
2009/060757 A1, and Japanese Patent Appln. Laying-Open No.
2013-183036 A1, etc. disclose organic electroluminescent devices
using a biscarbazole derivative as a host material. However, the
references fail to disclose an organic electroluminescent device
using a multi-component host comprising a biscarbazole derivative
and a carbazole derivative including a nitrogen-containing
heteroaryl.
DISCLOSURE OF THE INVENTION
Problems to be Solved
[0007] The objective of the present invention is to provide an
organic electroluminescent device having high efficiency and long
lifespan.
Solution to Problems
[0008] The present inventors found that 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, and a
second host compound is represented by the following formula 2:
##STR00001##
[0009] wherein
[0010] A.sub.1 and A.sub.2 each independently represent a
substituted or unsubstituted (C6-C30)aryl;
[0011] L.sub.1 represents a substituted or unsubstituted
(C6-C30)arylene;
[0012] X.sub.1 to X.sub.16 each independently represent hydrogen,
deuterium, a halogen, a cyano, a substituted or unsubstituted
(C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a
substituted or unsubstituted (C2-C30)alkynyl, a substituted or
unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted
(C6-C60)aryl, a substituted or unsubstituted (3- to
30-membered)heteroaryl, a substituted or unsubstituted
tri(C1-C30)alkylsilyl, a substituted or unsubstituted
tri(C6-C30)arylsilyl, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted
(C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted
mono- or di-(C6-C30)arylamino; or are linked to an adjacent
substituent(s) 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;
##STR00002##
[0013] wherein
[0014] Ma represents a substituted or unsubstituted
nitrogen-containing (5- to 11-membered)heteroaryl;
[0015] La represents a single bond, or a substituted or
unsubstituted (C6-C30)arylene;
[0016] Xa to Xh each independently represent hydrogen, deuterium, a
halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a
substituted or unsubstituted (C2-C30)alkenyl, a substituted or
unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted
(C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a
substituted or unsubstituted (3- to 30-membered)heteroaryl, a
substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted
or unsubstituted tri(C6-C30)arylsilyl, a substituted or
unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or
unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an
adjacent substituent(s) 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; and the heteroaryl
contains at least one hetero atom selected from B, N, O, S,
P(.dbd.O), Si, and P.
Effects of the Invention
[0017] According to the present invention, an organic
electroluminescent device having high efficiency and long lifespan
is provided, and it is possible to manufacture a display device or
a lighting device using the organic electroluminescent device.
EMBODIMENTS OF THE INVENTION
[0018] 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.
[0019] Hereinafter, the organic electroluminescent device
comprising the organic electroluminescent compounds of formulae 1
and 2 will be described in detail.
[0020] The compound represented by formula 1 can be represented by
formula 3, 4, 5, or 6:
##STR00003##
wherein
[0021] A.sub.1, A.sub.2, L.sub.1, and X.sub.1 to X.sub.16 are as
defined in formula 1.
[0022] In formula 1 above, A.sub.1 and A.sub.2 each independently
represent a substituted or unsubstituted (C6-C30)aryl, preferably,
each independently represent a substituted or unsubstituted
(C6-C18)aryl, more preferably, each independently represent a
(C6-C18)aryl unsubstituted or substituted with a cyano, a
(C1-C6)alkyl, a (C6-C12)aryl, or a tri(C6-C12)arylsilyl, and even
more preferably, each independently represent phenyl, biphenyl,
terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl,
indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl,
or fluoranthenyl.
[0023] In formula 1 above, X.sub.1 to X.sub.16 each independently
represent hydrogen, deuterium, a halogen, a cyano, a substituted or
unsubstituted (C1-C30)alkyl, a substituted or unsubstituted
(C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a
substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or
unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to
30-membered)heteroaryl, a substituted or unsubstituted
tri(C1-C30)alkylsilyl, a substituted or unsubstituted
tri(C6-C30)arylsilyl, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted
(C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted
mono- or di-(C6-C30)arylamino; or are linked to an adjacent
substituent(s) 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, preferably, each independently
represent hydrogen, a cyano, a substituted or unsubstituted
(C6-C20)aryl, a substituted or unsubstituted (5- to
20-membered)heteroaryl, or a substituted or unsubstituted
tri(C6-C12)arylsilyl, and more preferably, each independently
represent hydrogen, a cyano, a (C6-C20)aryl unsubstituted or
substituted with a cyano, an unsubstituted (5- to
20-membered)heteroaryl, or an unsubstituted
tri(C6-C12)arylsilyl.
[0024] In formula 1 above, L.sub.1 represents a substituted or
unsubstituted (C6-C30)arylene, preferably, represents a substituted
or unsubstituted (C6-C15)arylene, and more preferably, represents a
(C6-C15)arylene unsubstituted or substituted with a cyano, a
(C1-C6)alkyl, or a tri(C6-C12)arylsilyl.
[0025] In addition, L.sub.1 can be represented by one of formulae 7
to 19:
##STR00004## ##STR00005## ##STR00006##
[0026] wherein
[0027] Xi to Xp each independently represent hydrogen, deuterium, a
halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a
substituted or unsubstituted (C2-C30)alkenyl, a substituted or
unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted
(C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a
substituted or unsubstituted (3- to 30-membered)heteroaryl, a
substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted
or unsubstituted tri(C6-C30)arylsilyl, a substituted or
unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or
unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or
unsubstituted mono- or di-(C6-C30)arylamino; or are linked to an
adjacent substituent(s) 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.
[0028] Preferably, Xi to Xp may each independently represent
hydrogen, a halogen, a cyano, a (C1-C10)alkyl, a
(C3-C20)cycloalkyl, a (C6-C12)aryl, a
(C1-C6)alkyldi(C6-C12)arylsilyl, or a tri(C6-C12)arylsilyl, and
more preferably, each independently represent hydrogen, a cyano, a
(C1-C6)alkyl, or a tri(C6-C12)arylsilyl.
[0029] In formula 2 above, Ma represents a substituted or
unsubstituted nitrogen-containing (5- to 11-membered)heteroaryl,
preferably, represents a substituted or unsubstituted
nitrogen-containing (6- to 10-membered)heteroaryl, and more
preferably, represents a nitrogen-containing (6- to
10-membered)heteroaryl substituted with an unsubstituted
(C6-C18)aryl, a (C6-C12)aryl substituted with a cyano, a
(C6-C12)aryl substituted with a (C1-C6)alkyl, a (C6-C12)aryl
substituted with a tri(C6-C12)arylsilyl, or a (6- to
15-membered)heteroaryl.
[0030] In addition, Ma may represent a monocyclic heteroaryl
selected from the group consisting of pyrrolyl, imidazolyl,
pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl,
pyrazinyl, pyrimidinyl, and pyridazinyl, or a fused heteroaryl
selected from the group consisting of benzoimidazolyl, isoindolyl,
indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl,
cinnolinyl, quinazolinyl, naphthyridinyl, and quinoxalinyl, and
preferably may represent triazinyl, pyrimidinyl, pyridyl, quinolyl,
isoquinolyl, quinazolinyl, naphthyridinyl, or quinoxalinyl.
[0031] In formula 2 above, La represents a single bond, or a
substituted or unsubstituted (C6-C30)arylene, preferably,
represents a single bond, or a substituted or unsubstituted
(C6-C12)arylene, and more preferably, represents a single bond, or
a (C6-C12)arylene unsubstituted or substituted with a
tri(C6-C10)arylsilyl.
[0032] In addition, La can represent a single bond, or be
represented by one of formulae 7 to 19 as above.
[0033] In formula 2 above, Xa to Xh each independently represent
hydrogen, deuterium, a halogen, a cyano, a substituted or
unsubstituted (C1-C30)alkyl, a substituted or unsubstituted
(C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a
substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or
unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to
30-membered)heteroaryl, a substituted or unsubstituted
tri(C1-C30)alkylsilyl, a substituted or unsubstituted
tri(C6-C30)arylsilyl, a substituted or unsubstituted
di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted
mono- or di-(C6-C30)arylamino; or are linked to an adjacent
substituent(s) 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, preferably, each independently
represent hydrogen, a cyano, a substituted or unsubstituted
(C6-C15)aryl, a substituted or unsubstituted (10- to
20-membered)heteroaryl, or a substituted or unsubstituted
tri(C6-C10)arylsilyl; or are linked to an adjacent substituent(s)
to form a substituted or unsubstituted, mono- or polycyclic,
(C6-C20) aromatic ring, and more preferably, each independently
represent hydrogen; a cyano; a (C6-C15)aryl unsubstituted or
substituted with a tri(C6-C10)arylsilyl; a (10- to
20-membered)heteroaryl unsubstituted or substituted with a
(C6-C12)aryl or a cyano(C6-C12)aryl; or an unsubstituted
tri(C6-C10)arylsilyl; or are linked to an adjacent substituent(s)
to form a substituted or unsubstituted benzene, a substituted or
unsubstituted indole, a substituted or unsubstituted benzoindole, a
substituted or unsubstituted indene, a substituted or unsubstituted
benzofuran, or a substituted or unsubstituted benzothiophene.
[0034] Herein, "(C1-C30)alkyl" is meant to be a linear or branched
alkyl 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 meant to be 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 3 to 7 ring
backbone atoms, preferably 5 to 7, including at least one
heteroatom selected from B, N, O, S, P(.dbd.O), Si and P,
preferably O, S and N, 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, binaphthyl, phenylnaphthyl, naphthylphenyl,
fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl,
phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl,
triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl,
naphthacenyl, fluoranthenyl, etc.; "(3- to 30-membered)heteroaryl"
is an aryl having 3 to 30 ring backbone atoms, including at least
one, preferably 1 to 4 heteroatoms selected from the group
consisting of B, N, O, S, P(.dbd.O), Si and P; 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
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, benzoindolyl,
indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl,
quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl,
phenanthridinyl, benzodioxolyl, etc.; "nitrogen-containing (5- to
30-membered)heteroaryl" is an aryl having 5 to 30 ring backbone
atoms, preferably 5 to 20, and more preferably 5 to 15, including
at least one heteroatom, N; 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.
Further, "halogen" includes F, Cl, Br, and I.
[0035] 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.
The substituents of the substituted alkyl, the substituted alkenyl,
the substituted alkynyl, the substituted cycloalkyl, the
substituted aryl(ene), the substituted heteroaryl, the substituted
trialkylsilyl, the substituted triarylsilyl, the substituted
dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted
mono- or di-arylamino, and the substituted nitrogen-containing
heteroaryl in A.sub.1, A.sub.2, L.sub.1, X.sub.1 to X.sub.16, Ma,
La, and Xa to Xh in formulae 1 and 2 each independently are at
least one selected from the group consisting of deuterium, a
halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl,
a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a
(C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a
(C3-C30)cycloalkenyl, a (3- to 7-membered)heterocycloalkyl, a
(C6-C30)aryloxy, a (C6-C30)arylthio, a (3- to
30-membered)heteroaryl unsubstituted or substituted with a
(C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a
cyano, a (3- to 30-membered)heteroaryl, or a tri(C6-C30)arylsilyl,
a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a
di(C1-C30)alkyl(C6-C30)arylsilyl, a
(C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono- or
di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a
(C1-C30)alkyl(C6-C30)arylamino, a (C1-C30)alkylcarbonyl, a
(C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a
di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a
(C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and
a (C1-C30)alkyl(C6-C30)aryl, and preferably are at least one
selected from the group consisting of a cyano, a (C1-C6)alkyl, a
(5- to 15-membered)heteroaryl, a (C6-C18)aryl unsubstituted or
substituted with a cyano or a tri(C6-C12)arylsilyl, a
tri(C6-C12)arylsilyl, and a (C1-C6)alkyl(C6-C12)aryl.
[0036] In formula 1, a triarylsilyl as X.sub.1 to X.sub.16 is
preferably a triphenylsilyl.
[0037] The first host compound represented by formula 1 includes
the following compounds, but is not limited thereto:
##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##
[0038] The second host compound represented by formula 2 includes
the following compounds, but is not limited thereto:
##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## ##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##
[0039] The organic electroluminescent device according to the
present invention comprises an anode; a cathode; and at least one
organic layer between the anode and the cathode. The organic layer
comprises a light-emitting layer, and 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, and
a second host compound is represented by formula 2.
[0040] The light-emitting layer is a layer from which light is
emitted, and can be a single layer or a multi layer of which two or
more layers are stacked. In the light-emitting layer, it is
preferable that the doping concentration of the dopant compound
based on the host compound is less than 20 wt %.
[0041] The organic layer comprises a light-emitting layer, and may
further comprise at least one layer selected from the group
consisting of a hole injection layer, a hole transport layer, an
electron transport layer, an electron injection layer, an
interlayer, a hole blocking layer, and an electron blocking
layer.
[0042] According to the organic electroluminescent device of the
present invention, the weight ratio of the first host material to
the second host material is in the range of 1:99 to 99:1. The
dopant is preferably at least one phosphorescent dopant. The dopant
materials applied to the organic electroluminescent device
according to the present invention are not limited, but may be
preferably selected from metallated complex compounds of iridium,
osmium, copper and platinum, more preferably selected from
ortho-metallated complex compounds of iridium, osmium, copper and
platinum, and even more preferably ortho-metallated iridium complex
compounds.
[0043] The phosphorescent dopant is preferably selected from
compounds represented by the following formulae 101 to 103.
##STR00227##
[0044] wherein L is selected from the following structures:
##STR00228##
[0045] R.sub.100 represents hydrogen, a substituted or
unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted
(C3-C30)cycloalkyl;
[0046] 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 unsubstituted or substituted with deuterium or a
halogen(s), a cyano, a substituted or unsubstituted (C1-C30)alkoxy,
a substituted or unsubstituted (C6-C30)aryl, or a substituted or
unsubstituted (C3-C30)cycloalkyl; adjacent substituents of
R.sub.106 to R.sub.109 may be linked to each other to form a
substituted or unsubstituted fused ring, e.g., fluorene
unsubstituted or substituted with alkyl, dibenzothiophene
unsubstituted or substituted with alkyl, or dibenzofuran
unsubstituted or substituted with alkyl; and adjacent substituents
of R.sub.120 to R.sub.123 may be linked to each other to form a
substituted or unsubstituted fused ring, e.g., quinoline
unsubstituted or substituted with halogen, alkyl, or aryl;
[0047] R.sub.124 to R.sub.127 each independently represent
hydrogen, deuterium, a halogen, a substituted or unsubstituted
(C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and
adjacent substituents of R.sub.124 to R.sub.127 may be linked to
each other to form a substituted or unsubstituted fused ring, e.g.,
fluorene unsubstituted or substituted with alkyl, dibenzothiophene
unsubstituted or substituted with alkyl, or dibenzofuran
unsubstituted or substituted with alkyl;
[0048] R.sub.201 to R.sub.211 each independently represent
hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or
substituted with deuterium or a halogen(s), a substituted or
unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted
(C6-C30)aryl; and adjacent substituents of R.sub.205 to R.sub.211
may be linked to each other to form a substituted or unsubstituted
fused ring, e.g., fluorene unsubstituted or substituted with alkyl,
dibenzothiophene unsubstituted or substituted with alkyl, or
dibenzofuran unsubstituted or substituted with alkyl;
[0049] 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
[0050] e represents an integer of 1 to 3.
[0051] Specifically, the phosphorescent dopant materials include
the following:
##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##
[0052] The organic electroluminescent device according to the
present invention may further comprise at least one compound
selected from the group consisting of arylamine-based compounds and
styrylarylamine-based compounds in the organic layer.
[0053] In addition, in the organic electroluminescent device
according to 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
4.sup.th period, transition metals of the 5.sup.th period,
lanthanides and organic metals of d-transition elements of the
Periodic Table, or at least one complex compound comprising said
metal.
[0054] According to the present invention, at least one layer
(hereinafter, "a surface layer") is preferably placed on an inner
surface(s) of one or both electrode(s); selected from a
chalcogenide layer, a metal halide layer and a metal oxide layer.
Specifically, a chalcogenide (including oxides) layer of silicon or
aluminum is preferably placed on an anode surface of an
electroluminescent medium layer, and a metal halide layer or a
metal oxide layer is preferably placed on a cathode surface of an
electroluminescent medium layer. Such a surface layer provides
operation stability for the organic electroluminescent device.
Preferably, said chalcogenide includes
SiO.sub.x(1.ltoreq.X.ltoreq.2), AlO.sub.x(1.ltoreq.X.ltoreq.1.5),
SiON, SiAlON, etc.; said metal halide includes LiF, MgF.sub.2,
CaF.sub.2, a rare earth metal fluoride, etc.; and said metal oxide
includes Cs.sub.2O, Li.sub.2O, MgO, SrO, BaO, CaO, etc.
[0055] Between the anode and the light-emitting layer, a layer
selected from a hole injection layer, a hole transport layer, or an
electron blocking layer, or formed by a combination thereof can be
used. Multi layers can be used for the hole injection layer in
order to lower the hole injection barrier (or hole injection
voltage) from the anode to the hole transport layer or the electron
blocking layer. Two compounds can be simultaneously used in each
layer. The hole transport layer and the electron blocking layer can
also be formed of multi layers.
[0056] Between the light-emitting layer and the cathode, a layer
selected from an electron buffer layer, a hole blocking layer, an
electron transport layer, or an electron injection layer, or formed
by a combination thereof can be used. Multi layers can be used for
the electron buffer layer in order to control the injection of the
electrons and enhance the interfacial characteristics between the
light-emitting layer and the electron injection layer. Two
compounds can be simultaneously used in each layer. The hole
blocking layer and the electron transport layer can also be formed
of multi layers, and each layer can comprise two or more
compounds.
[0057] In the organic electroluminescent device according to 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 is preferably 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
an electroluminescent 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 the electroluminescent
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
electroluminescent device having two or more electroluminescent
layers and emitting white light.
[0058] In order to form each layer of the organic
electroluminescent device of the present invention, dry
film-forming methods such as vacuum evaporation, sputtering, plasma
and ion plating methods, or wet film-forming methods such as ink
jet printing, nozzle printing, slot coating, spin coating, dip
coating, and flow coating methods can be used. The first and second
host compounds of the present invention may be co-evaporated or
mixture-evaporated.
[0059] When using a wet film-forming method, a thin film can be
formed by dissolving or diffusing materials forming each layer into
any suitable solvent such as ethanol, chloroform, tetrahydrofuran,
dioxane, etc. The solvent can be any solvent where the materials
forming each layer can be dissolved or diffused, and where there
are no problems in film-formation capability.
[0060] Herein, a co-evaporation indicates a process for two or more
materials to be deposited as a mixture, by introducing each of the
two or more materials into respective crucible cells, and applying
an electric current to the cells for each of the materials to be
evaporated. Herein, a mixture-evaporation indicates a process for
two or more materials to be deposited as a mixture, by mixing the
two or more materials in one crucible cell before the deposition,
and applying an electric current to the cell for the mixture to be
evaporated.
[0061] By using the organic electroluminescent device of the
present invention, a display system or a lighting system can be
produced.
[0062] Hereinafter, the luminescent properties of the device
comprising the host compound of the present invention will be
explained in detail with reference to the following examples.
Device Examples 1-1 to 1-6: Preparation of an OLED Device by
Co-Evaporating the First Host Compound and the Second Host Compound
of the Present Invention
[0063] An OLED device was produced using the organic
electroluminescent compound according to the present invention. A
transparent electrode indium tin oxide (ITO) thin film (10
.OMEGA./sq) on a glass substrate for an organic light-emitting
diode (OLED) device (Geomatec) was subjected to an ultrasonic
washing with trichloroethylene, acetone, ethanol, and distilled
water, sequentially, and then was stored in isopropanol. The ITO
substrate was then 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-carbazol-3-yl)-
-[1,1'-biphenyl]-4,4'-diamine (compound HI-1) was introduced into a
cell of said vacuum vapor depositing apparatus, and then the
pressure in the chamber of said apparatus was controlled to
10.sup.-6 torr. Thereafter, an electric current was applied to the
cell to evaporate the above introduced material, thereby forming a
first hole injection layer having a thickness of 80 nm on the ITO
substrate. Next, 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile
(compound HI-2) was introduced into another cell of said vacuum
vapor depositing apparatus, and was evaporated by applying an
electric current to the cell, thereby forming a second hole
injection layer having a thickness of 5 nm on the first hole
injection layer.
N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phe-
nyl)-9H-fluorene-2-amine (compound HT-1) was then introduced into
another cell of said vacuum vapor depositing apparatus, and was
evaporated by applying an electric current to the cell, thereby
forming a first hole transport layer having a thickness of 10 nm on
the second hole injection layer. Afterwards,
N,N-di([1,1'-biphenyl]-4-yl)-4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amin-
e (compound HT-2) was introduced into another cell of said vacuum
vapor depositing apparatus, and was evaporated by applying an
electric current to the cell, thereby forming a second hole
transport layer having a thickness of 60 nm on the first hole
transport layer. As a host material, a first host compound and a
second host compound were introduced into two cells of the vacuum
vapor depositing apparatus, respectively. A dopant compound D-96
was introduced into another cell. The two host materials were
evaporated at 1:1 rate, while the dopant was evaporated at a
different rate from the host materials, so that the dopant was
deposited in a doping amount of 3 wt % based on the total amount of
the host and dopant to form a light-emitting layer having a
thickness of 40 nm on the hole transport layer.
2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine
(compound ET-1) and lithium quinolate (compound EI-1) were then
introduced into two cells of the vacuum vapor depositing apparatus,
respectively, and evaporated at 1:1 rate to form an electron
transport layer having a thickness of 30 nm on the light-emitting
layer. After depositing lithium quinolate (compound EI-1) as an
electron injection layer having a thickness of 2 nm on the electron
transport layer, an Al cathode having a thickness of 80 nm was
deposited by another vacuum vapor deposition apparatus. Thus, an
OLED device was produced.
##STR00277## ##STR00278## ##STR00279##
Comparative Examples 1-1 to 1-3: Preparation of an OLED Device
Using Only the Second Host Compound as a Host
[0064] An OLED device was produced in the same manner as in Device
Examples 1-1 to 1-6, except for using only the second host compound
as a host of the light-emitting layer.
[0065] The driving voltage at 1,000 nit, luminous efficiency, CIE
color coordinate, and the time taken for the luminance at 5,000 nit
to be reduced from 100% to 80% at a constant current of the OLEDs
produced as above were measured.
[0066] Table 1 below shows the luminous characteristics of the
organic electroluminescent devices produced as in the examples
above.
TABLE-US-00001 TABLE 1 Voltage Efficiency Color Lifespan Device No.
HTL Host Dopant [V] [cd/A] Coordinate (x, y) [hr] Example HT-1/HT-2
H1-1:H2-2 D-96 4.4 27.5 0.664, 0.335 1,280 1-1 Example HT-1/HT-2
H1-7:H2-29 D-96 3.9 27.7 0.665, 0.332 550 1-2 Example HT-1/HT-2
H1-19:H2-29 D-96 4.1 24.6 0.664, 0.332 470 1-3 Example HT-1/HT-2
H1-36:H2-154 D-96 4.6 27.8 0.663, 0.335 1,530 1-4 Example HT-1/HT-2
H1-36:H2-29 D-96 3.7 28.2 0.666, 0.331 780 1-5 Example HT-1/HT-2
H1-36:H2-155 D-96 4.6 26.9 0.664, 0.335 970 1-6 Comp. Ex. HT-1/HT-2
H2-2 D-96 4.1 28.2 0.662, 0.337 300 1-1 Comp. Ex. HT-1/HT-2 H2-154
D-96 4.5 27.1 0.662, 0.337 420 1-2 Comp. Ex. HT-1/HT-2 H2-29 D-96
3.6 27.5 0.668, 0.331 310 1-3
Device Examples 2-1 to 2-7: Preparation of an OLED Device by
Co-Evaporating the First Host Compound and the Second Host Compound
of the Present Invention
[0067] An OLED device was produced in the same manner as in Device
Examples 1-1 to 1-6, except for forming the second hole injection
layer of 3 nm; forming the first hole transport layer of 40 nm; not
forming the second hole transport layer; doping compound D-25 as
the dopant of the light-emitting layer in a doping amount of 15 wt
% based on the total amount of the host and dopant; forming the
electron transport layer of 35 nm by evaporating
2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine
and lithium quinolate at a rate of 4:6; and using other
combinations for the first host compound and the second host
compound used in the host of the light-emitting layer.
Device Examples 2-8 to 2-9: Preparation of an OLED Device by
Co-Evaporating the First Host Compound and the Second Host Compound
of the Present Invention
[0068] An OLED device was produced in the same manner as in Device
Examples 1-1 to 1-6, except for forming the second hole injection
layer of 3 nm; forming the first hole transport layer of 40 nm; not
forming the second hole transport layer; doping compound D-1 as the
dopant of the light-emitting layer in a doping amount of 15 wt %
based on the total amount of the host and dopant; forming the
electron transport layer of 35 nm by evaporating
2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine
and lithium quinolate at a rate of 4:6; and using other
combinations for the first host compound and the second host
compound used in the host of the light-emitting layer.
Device Example 2-10: Preparation of an OLED Device by
Co-Evaporating the First Host Compound and the Second Host Compound
of the Present Invention
[0069] An OLED device was produced in the same manner as in Device
Examples 1-1 to 1-6, except for forming the second hole injection
layer of 3 nm; forming the first hole transport layer of 40 nm; not
forming the second hole transport layer; doping compound D-136 as
the dopant of the light-emitting layer in a doping amount of 15 wt
% based on the total amount of the host and dopant; forming the
electron transport layer of 35 nm by evaporating
2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine
and lithium quinolate at a rate of 4:6; and using other
combinations for the first host compound and the second host
compound used in the host of the light-emitting layer.
Device Examples 3-1 to 3-3: Preparation of an OLED Device by
Co-Evaporating the First Host Compound and the Second Host Compound
of the Present Invention
[0070] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-7, except for forming the first hole injection
layer of 10 nm; forming the second hole transport layer of 30 nm
using compound HT-3; using compound D-136 as the dopant of the
light-emitting layer; and using other combinations for the first
host compound and the second host compound used in the host of the
light-emitting layer.
Device Example 3-4: Preparation of an OLED Device by Co-Evaporating
the First Host Compound and the Second Host Compound of the Present
Invention
[0071] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-7, except for forming the first hole injection
layer of 10 nm; forming the second hole transport layer of 30 nm
using compound HT-3; using compound D-168 as the dopant of the
light-emitting layer; and using other combinations for the first
host compound and the second host compound used in the host of the
light-emitting layer.
Comparative Examples 2-1 to 2-3: Preparation of an OLED Device
Using Only the First Host Compound as a Host
[0072] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-7, except for using only the first host compound
as a host of the light-emitting layer.
Comparative Examples 3-1 to 3-3: Preparation of an OLED Device
Using Only the Second Host Compound as a Host
[0073] An OLED device was produced in the same manner as in Device
Examples 2-1 to 2-7, except for using only the second host compound
as a host of the light-emitting layer.
Comparative Examples 3-4 to 3-6: Preparation of an OLED Device
Using Only the Second Host Compound as a Host
[0074] An OLED device was produced in the same manner as in Device
Examples 2-8 to 2-9, except for using only the second host compound
as a host of the light-emitting layer.
Comparative Examples 4-1 to 4-3: Preparation of an OLED Device
Using Only the Second Host Compound as a Host
[0075] An OLED device was produced in the same manner as in Device
Examples 3-1 to 3-3, except for using only the second host compound
as a host of the light-emitting layer.
[0076] The driving voltage at 1,000 nit, luminous efficiency, CIE
color coordinate, and the time taken for the luminance at 15,000
nit to be reduced from 100% to 80% at a constant current of the
OLEDs produced as above were measured.
[0077] Table 2 below shows the luminous characteristics of the
organic electroluminescent devices produced as in the examples
above.
TABLE-US-00002 TABLE 2 Color Voltage Efficiency Coordinate Lifespan
Device No. HTL Host Dopant [V] [cd/A] (x, y) [hr] Example HT-1
H1-1:H2-25 D-25 3.2 49.8 0.301, 0.658 350 2-1 Example HT-1
H1-1:H2-31 D-25 3 57.1 0.308, 0.655 380 2-2 Example HT-1 H1-1:H2-48
D-25 2.9 56.8 0.305, 0.656 400 2-3 Example HT-1 H1-1:H2-101 D-25 3
55.5 0.303, 0.657 230 2-4 Example HT-1 H1-1:H2-34 D-25 3.1 58.1
0.306, 0.655 440 2-5 Example HT-1 H1-4:H2-31 D-25 3 53.3 0.304,
0.656 120 2-6 Example HT-1 H1-37:H2-31 D-25 3 53.7 0.306, 0.655 300
2-7 Example HT-1 H1-1:H2-31 D-1 2.9 53 0.321, 0.656 560 2-8 Example
HT-1 H1-1:H2-48 D-1 2.8 55.3 0.319, 0.657 550 2-9 Example HT-1
H1-113:H2-31 D-136 2.8 59.4 0.331, 0.655 600 2-10 Example HT-1/HT-3
H1-1:H2-48 D-136 3.1 67.5 0.326, 0.658 590 3-1 Example HT-1/HT-3
H1-1:H2-273 D-136 3.1 66.2 0.328, 0.657 700 3-2 Example HT-1/HT-3
H1-113:H2-125 D-136 3.1 65.8 0.329, 0.657 700 3-3 Example HT-1/HT-3
H1-1:H2-273 D-168 3.0 57.2 0.288, 0.665 450 3-4 Comp. Ex. HT-1 H1-1
D-25 6.8 3.1 0.301, 0.653 x 2-1 Comp. Ex. HT-1 H1-4 D-25 7.2 3.6
0.295, 0.658 x 2-2 Comp. Ex. HT-1 H1-37 D-25 7.0 3.0 0.302, 0.653 x
2-3 Comp. Ex. HT-1 H2-31 D-25 2.9 42.8 0.314, 0.652 100 3-1 Comp.
Ex. HT-1 H2-101 D-25 2.8 50.3 0.315, 0.651 60 3-2 Comp. Ex. HT-1
H2-34 D-25 2.7 49.2 0.312, 0.652 100 3-3 Comp. Ex. HT-1 H2-31 D-1
2.9 33.5 0.323, 0.653 390 3-4 Comp. Ex. HT-1 H2-48 D-1 2.6 41.2
0.325, 0.653 380 3-5 Comp. Ex. HT-1 H2-87 D-1 2.8 37.9 0.323, 0.653
420 3-6 Comp. Ex. HT-1/HT-3 H2-48 D-136 2.6 51.9 0.334, 0.652 490
4-1 Comp. Ex. HT-1/HT-3 H2-125 D-136 3.0 64.9 0.337, 0.649 360 4-2
Comp. Ex. HT-1/HT-3 H2-273 D-136 3.3 68.2 0.332, 0.654 440 4-3
Device Example 4-1: Preparation of an OLED Device by Co-Evaporating
the First Host Compound and the Second Host Compound of the Present
Invention
[0078] An OLED device was produced in the same manner as in Device
Examples 1-1 to 1-6, except for using compound HT-4 for the second
hole transport layer, and using the compounds as listed in Table 3
below for the first host compound and the second host compound used
in the host of the light-emitting layer.
Comparative Example 5-1: Preparation of an OLED Device Using Only
the Second Host Compound as a Host
[0079] An OLED device was produced in the same manner as in Device
Example 4-1, except for using only the second host compound of
Table 3 as a host of the light-emitting layer.
[0080] The driving voltage at 1,000 nit, luminous efficiency, CIE
color coordinate, and the time taken for the luminance at 5,000 nit
to be reduced from 100% to 90% at a constant current of the OLEDs
produced as above were measured.
[0081] Table 3 below shows the luminous characteristics of the
organic electroluminescent devices produced as in the examples
above.
TABLE-US-00003 TABLE 3 Voltage Efficiency Color Lifespan Device No.
HTL Host Dopant [V] [cd/A] Coordinate (x, y) [hr] Example HT-1/HT-4
H1-7:H2-41 D-96 3.4 30.7 0.665, 0.333 400 4-1 Comp. Ex. HT-1/HT-4
H2-41 D-96 3.1 28.3 0.668, 0.331 300 5-1
[0082] The organic electroluminescent device of the present
invention comprises a light-emitting layer comprising a host and a
phosphorus dopant, and the host consists of a specific combination
of multi-component host compounds. The device of the present
invention provides superior lifespan characteristics to
conventional devices.
* * * * *