U.S. patent application number 16/162833 was filed with the patent office on 2019-03-14 for organic electroluminescent compound and organic electroluminescent device containing the same.
The applicant listed for this patent is INT TECH CO., LTD.. Invention is credited to MENG-HUNG HSIN.
Application Number | 20190081247 16/162833 |
Document ID | / |
Family ID | 64176724 |
Filed Date | 2019-03-14 |
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United States Patent
Application |
20190081247 |
Kind Code |
A1 |
HSIN; MENG-HUNG |
March 14, 2019 |
ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT
DEVICE CONTAINING THE SAME
Abstract
The present disclosure provides an organic electroluminescent
compound represented by the following formula (II): ##STR00001##
wherein each of R.sub.1 to R.sub.12 independently represents
hydrogen, deuterium, a halogen, a substituted or unsubstituted
(C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl
group, or a substituted or unsubstituted 3- to 30-membered
heteroaryl group; or is linked to one or more adjacent substituents
to form a mono- or polycyclic, alicyclic or aromatic ring whose
carbon atom(s) may be replaced by at least one atom selected from
nitrogen, oxygen and sulfur; and the heteroaryl group contains at
least one atom selected from B, N, O, S, P(.dbd.O), Si and P.
Inventors: |
HSIN; MENG-HUNG; (NEW TAIPEI
CITY, TW) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
INT TECH CO., LTD. |
HSINCHU COUNTY |
|
TW |
|
|
Family ID: |
64176724 |
Appl. No.: |
16/162833 |
Filed: |
October 17, 2018 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
15703506 |
Sep 13, 2017 |
10135001 |
|
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16162833 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07D 213/06 20130101;
C07D 405/14 20130101; C07D 409/14 20130101; H01L 51/0068 20130101;
C09K 2211/1018 20130101; H01L 51/0065 20130101; H01L 51/0067
20130101; C07D 401/14 20130101; C07F 7/0812 20130101; H01L 51/0054
20130101; H01L 51/005 20130101; H01L 51/0055 20130101; H01L 51/0094
20130101; C09K 11/06 20130101; H01L 51/0052 20130101; H01L 51/5016
20130101; C07D 471/04 20130101; C07F 5/027 20130101; H01L 51/0058
20130101; H01L 51/0072 20130101; C09K 2211/1011 20130101; H01L
51/5012 20130101 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C09K 11/06 20060101 C09K011/06 |
Claims
1. An organic electroluminescent compound represented by the
following formula (II): ##STR00006## wherein each of R.sub.1 to
R.sub.12 independently represents hydrogen, deuterium, a halogen, a
substituted or unsubstituted (C1-C30) alkyl group, a substituted or
unsubstituted (C6-C30) aryl group, or a substituted or
unsubstituted 3- to 30-membered heteroaryl group; or is linked to
one or more adjacent substituents to form a mono- or polycyclic,
alicyclic or aromatic ring whose carbon atom(s) may be replaced by
at least one atom selected from nitrogen, oxygen and sulfur; and
the heteroaryl group contains at least one atom selected from B, N,
O, S, P(.dbd.O), Si and P.
2. The organic electroluminescent compound of claim 1, wherein each
of the substituents of the substituted groups in R.sub.1 to
R.sub.12 independently includes at least one selected from the
group consisting of deuterium, a halogen, a (C1-C30)alkyl group, a
(C1-C30)alkyl group substituted with a halogen, a (C6-C30)aryl
group, a 3- to 30-membered heteroaryl group, a 3- to 30-membered
heteroaryl group substituted with a (C6-C30)aryl group, a
(C6-C30)aryl group substituted with a 3- to 30-membered heteroaryl
group, a (C3-C30)cycloalkyl group, a 5- to 7-membered
heterocycloalkyl group, 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, a (C2-C30)alkenyl
group, a (C2-C30)alkynyl group, a cyano group, a
di(C1-C30)alkylamino group, a di(C6-C30)arylamino group, a
(C1-C30)alkyl(C6-C30)arylamino 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, a (C1-C30)alkyl(C6-C30)aryl group, a carboxyl group, a nitro
group, and a hydroxyl group.
2. The organic electroluminescent compound of claim 2, wherein each
of R.sub.1 to R.sub.12 is independently substituted with at least
one selected from the group consisting of deuterium, chloro,
fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,
t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl,
2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl,
perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl,
phenyl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl,
chrysenyl, naphthacenyl, perylenyl, fluorotrimethylsilyl,
triethylsilyl, tripropylsilyl, tri(t-butyl)silyl,
t-butyldimethylsilyl, dimethylphenylsilyl, carbazolyl and
triphenylsilyl, and more preferably at least one selected from the
group consisting of deuterium, chloro, fluoro, methyl, ethyl,
n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl,
n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl and decyl.
4. The organic electroluminescent compound of claim 1, wherein the
aryl group includes a monocyclic ring or fused ring, each of whose
rings has 4 to 7 ring backbone atoms.
5. The organic electroluminescent compound of claim 1, wherein the
aryl group includes phenyl, biphenyl, terphenyl, naphthyl, anthryl,
indenyl, fluorenyl, phenanthrenyl, triphenylenyl, pyrenyl,
perylenyl, chrysenyl, naphthacenyl, and fluoranthenyl, wherein said
naphthyl includes 1-naphthyl and 2-naphthyl, said anthryl includes
1-anthryl, 2-anthryl and 9-anthryl and said fluorenyl includes
1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and
9-fluorenyl.
6. The organic electroluminescent compound of claim 1, wherein the
heteroaryl group includes a monocyclic ring-type heteroaryl, a
fused ring-type heteroaryl, N-oxides thereof, and quaternary salts
thereof.
7. The organic electroluminescent compound of claim 6, wherein the
monocyclic ring-type heteroaryl includes furyl, thiophenyl,
pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl,
isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl,
tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl,
pyrimidinyl, and pyridazinyl.
8. The organic electroluminescent compound of claim 6, wherein the
fused ring-type heteroaryl includes benzofuranyl, benzothiophenyl,
isobenzofuranyl, benzoimidazolyl, benzothiazolyl,
benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl,
indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl,
cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl,
phenanthridinyl, benzodioxolyl, dibenzofuranyl, and
dibenzothiophenyl.
Description
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This application is a Divisional Application of U.S. patent
application Ser. No. 15/703,506, filed Sep. 13, 2017. The entire
disclosure of the patent application is incorporated herein by
reference.
BACKGROUND
[0002] Due to great potential application to flexible display
devices, organic light emitting diodes (OLEDs) have recently become
very important to the scientific community and the display
industry, and now attract much focus in research and development.
An OLED is a light-emitting diode (LED) in which a film of organic
compounds is placed between two conductors and emits light in
response to excitation such as by an electric current. OLEDs are
useful in displays such as television screens, computer monitors,
mobile phones, and tablets. OLED devices are self-luminous devices,
and have been actively studied for their brightness, superior
visibility, and the ability to display clearer images in comparison
with liquid crystal devices.
[0003] However, the OLED device technology is currently
experiencing an obstacle in the development process. A main issue
is that light-emitting efficiency cannot meet practical demand, so
the development of the OLED technology is greatly limited. One of
the factors affecting the luminous efficiency of the OLED device is
the efficiency of transporting carriers, including electrons and
holes.
BRIEF DESCRIPTION OF THE DRAWINGS
[0004] Aspects of the present disclosure are best understood from
the following detailed description when read with the accompanying
figures. It is emphasized that, in accordance with the standard
practice in the industry, various features are not drawn to scale.
In fact, the dimensions of the various features may be arbitrarily
increased or reduced for clarity of discussion.
[0005] FIG. 1 is a view showing an embodiment of an organic
electroluminescent device in accordance with some embodiments of
the present disclosure.
DETAILED DESCRIPTION OF THE DISCLOSURE
[0006] The following disclosure provides many different
embodiments, or examples, for implementing different features of
the provided subject matter. Specific examples of components and
arrangements are described below to simplify the present
disclosure. These are, of course, merely examples and are not
intended to be limiting.
[0007] OLED compounds rely on the radiative decay of molecular
excited states (excitons) generated by recombination of electrons
and holes in a host transport material. The nature of excitation
results in interactions between electrons and holes that split the
excited states into bright singlets and dark triplets. Traditional
phosphorescent OLEDs rely on the mixing of singlet and triplet
states due to spin-orbital (SO) interaction. This results in energy
harvesting from all higher singlet and triplet states, followed by
phosphorescence (relatively short-lived emission from the excited
triplet). The shortened triplet lifetime reduces triplet exciton
annihilation by charges and other excitons.
[0008] Therefore, there is a need for OLEDs that can reach higher
excitation states without rapid degradation. It has now been
discovered that thermally activated delayed fluorescence (TADF) can
transfer population between singlet levels and triplet sublevels in
a relevant timescale, such as, for example, 110 .mu.s. The present
disclosure provides organic electroluminescent compounds that are
capable of fluorescing or phosphorescing at higher energy
excitation states than the traditional organic electroluminescent
compounds. The organic electroluminescent compounds of the present
disclosure may improve carrier transporting ability. In some
embodiments, the organic electroluminescent compounds of the
present disclosure can be used in an electronic device or an
optoelectronic device such as a light-emitting element,
light-emitting device or lighting device.
[0009] In some embodiments, the present invention provides an
organic electroluminescent compound represented by the following
formula (I):
##STR00002## [0010] wherein [0011] R.sub.1, R.sub.2, R.sub.3 and
R.sub.4 each independently represents a substituted or
unsubstituted (C6-C30) aryl group, a substituted or unsubstituted
3- to 30-membered heteroaryl group, --NR.sub.5R.sub.6,
--SiR.sub.7R.sub.8R.sub.9, a cyano group, a nitro group or a
hydroxyl group; [0012] R.sub.5 to R.sub.11 each independently
represents hydrogen, deuterium, a halogen, a substituted or
unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted
(C6-C30) aryl group or a substituted or unsubstituted 3- to
30-membered heteroaryl group; or is linked to one or more adjacent
substituents to form a mono- or polycyclic, alicyclic or aromatic
ring whose carbon atom(s) may be replaced by at least one atom
selected from nitrogen, oxygen and sulfur;
[0013] a and c each independently represents an integer of 1 to 3;
wherein a or c is an integer of 1 or more, and each of R.sub.1 or
each of R.sub.3 is the same or different;
[0014] b and d each independently represents an integer of 1 to 3;
wherein b or d is an integer of 1 or more, and each of R.sub.2 or
each of R.sub.4 is the same or different; and wherein the
heteroaryl group contains at least one atom selected from B, N, O,
S, P(.dbd.O), Si and P.
[0015] In some embodiments of the present disclosure, substituents
of the substituted groups in R.sub.1 to R.sub.4 and R.sub.5 to
R.sub.11 each independently includes at least one selected from the
group consisting of deuterium, a halogen, a (C1-C30)alkyl group, a
(C1-C30)alkyl group substituted with a halogen, a (C6-C30)aryl
group, a 3- to 30-membered heteroaryl group, a 3- to 30-membered
heteroaryl group substituted with a (C6-C30)aryl group, a
(C6-C30)aryl group substituted with a 3- to 30-membered heteroaryl
group, a (C3-C30)cycloalkyl group, a 5- to 7-membered
heterocycloalkyl group, a tri(C1-C30)alkylsily group, a
tri(C6-C30)arylsilyl group, a di(C1-C30)alkyl(C6-C30)arylsilyl
group, a (C1-C30)alkyldi(C6-C30)arylsilyl group, a (C2-C30)alkenyl
group, a (C2-C30)alkynyl group, a cyano group, a
di(C1-C30)alkylamino group, a di(C6-C30)arylamino group, a
(C1-C30)alkyl(C6-C30)arylamino 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, a (C1 -C30)alkyl(C6-C30)aryl group, a carboxyl group, a
nitro group and a hydroxyl group.
[0016] In some embodiments of the present disclosure, the terms
"alkyl" and "alkoxy," and any alkyl moiety that is comprised in
substituents, include both a linear structure and a branched
structure; and the term "cycloalkyl" includes a mono- or polycyclic
hydrocarbon or a substituted or unsubstituted (C7-C30) bicycloalkyl
group. The term "aryl" refers to an organic radical derived from an
aromatic hydrocarbon by removing one hydrogen atom; includes a
monocyclic ring or fused ring each of whose rings has 4 to 7,
preferably 5 or 6, ring backbone atoms; may be formed by linking
two or more aryl groups to one another via one or more single
bonds; and includes phenyl, biphenyl, terphenyl, naphthyl, anthryl,
indenyl, fluorenyl, phenanthrenyl, triphenylenyl, pyrenyl,
perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., wherein
said naphthyl includes 1-naphthyl and 2-naphthyl, said anthryl
includes 1-anthryl, 2-anthryl and 9-anthryl, and said fluorenyl
includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and
9-fluorenyl. The term "heteroaryl" refers to an aryl having 1 to 4
heteroatoms selected from the group consisting of B, N, O, S,
P(.dbd.O), Si and P, and carbon atoms as remaining ring backbone
atoms other than said heteroatom; is a monocyclic ring or fused
ring condensed with at least one benzene ring; may be partially
saturated; may be formed by linking at least one heteroaryl group
to another heteroaryl or aryl group via one or more single bonds;
may be a divalent aryl group whose ring backbone heteroatom is
oxidized or quaternarized, for example, to form an N-oxide or a
quaternary salt; 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., a
fused ring-type heteroaryl including benzofuranyl, benzothiophenyl,
isobenzofuranyl, henzoimidazolyl, benzothiazolyl,
benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl,
indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl,
cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl,
phenanthridinyl, benzodioxolyl, dibenzofuranyl, dibenzothiophenyl,
etc., N-oxides thereof (for example, pyridyl N-oxide, quinolyl
N-oxide), and quaternary salts thereof.
[0017] In some embodiments of the present disclosure, R.sub.1 to
R.sub.4 each independently represents hydrogen, deuterium, chloro,
fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,
t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl,
2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl,
perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl,
phenyl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl,
chrysenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl,
thiophenyl, imidazolyl, benzoimidazolyl, indenyl, pyrazinyl,
pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl,
dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl,
indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl,
benzoxazolyl, phenanthrolinyl or N-carbazolyl.
[0018] In some embodiments of the present disclosure, each of
R.sub.1 to R.sub.4 and R.sub.5 to R.sub.11 may independently be
further substituted with at least one selected from the group
consisting of deuterium, chloro, fluoro, methyl, ethyl, n-propyl,
i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl,
n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl,
hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl,
perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl,
fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl,
perylenyl, fluorotrimethylsilyl, triethylsilyl, tripropylsilyl,
tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl,
carbazolyl and triphenylsilyl, and more preferably at least one
selected from the group consisting of deuterium, chloro, fluoro,
methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl,
n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl,
n-nonyl and decyl.
[0019] Accordingly, in one embodiment, the present invention is an
organic electroluminescent compound represented by the following
formula (II):
##STR00003## [0020] wherein R.sub.1 to R.sub.12 each independently
represents hydrogen, deuterium, a halogen, a substituted or
unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted
(C6-C30) aryl group or a substituted or unsubstituted 3- to
30-membered heteroaryl group; or is linked to one or more adjacent
substituents to form a mono- or polycyclic, alicyclic or aromatic
ring whose carbon atom(s) may be replaced by at least one atom
selected from nitrogen, oxygen and sulfur; and the heteroaryl group
contains at least one atom selected from B, N, S, P(.dbd.O), Si and
P.
[0021] In some embodiments of the present disclosure, substituents
of the substituted groups in R.sub.1 to R.sub.12 include
independently at least one selected from the group consisting of
deuterium, a halogen, a (C1-C30)alkyl group, a (C1-C30)alkyl group
substituted with a halogen, a (C6-C30)aryl group, a 3- to
30-membered heteroaryl group, a 3- to 30-membered heteroaryl group
substituted with a (C6-C30)aryl group, a (C6-C30)aryl group
substituted with a 3- to 30-membered heteroaryl group, a
(C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl
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, a (C2-C30)alkenyl group, a
(C2-C30)alkynyl group, a cyano group, a di(C1-C30)alkyl amino
group, a di(C6-C30)arylamino group, a
(C1-C30)alkyl(C6-C30)arylamino group, a di(C6-C30)arylboronyl
group, di(C1-C30)alkylboronyl group, a
(C1-C30)alkyl(C6-C30)arylboronyl group, a (C6-C30)aryl(C1-C30)alkyl
group, a (C1-C30)alkyl(C6-C30)aryl group, a carboxyl group, a nitro
group, and a hydroxyl group.
[0022] In some embodiments of the present disclosure, the terms
"alkyl" and "alkoxy," and any alkyl moiety which is comprised in
substituents, include both a linear structure and a branched
structure; and the term "cycloalkyl" includes a mono- or polycyclic
hydrocarbon such as a substituted or unsubstituted (C7-C30)
bicycloalkyl group. The term "aryl" refers to an organic radical
derived from an aromatic hydrocarbon by removing one hydrogen atom;
includes a monocyclic ring or fused ring each of whose rings has 4
to 7, preferably 5 or 6, ring backbone atoms; may be formed by
linking two or more aryl groups to one another via one or more
single bonds; and includes phenyl, biphenyl, terphenyl, naphthyl,
anthryl, indenyl, fluorenyl, phenanthrenyl, triphenyienyl, pyrenyl,
perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., wherein
said naphthyl includes 1-naphthyl and 2-naphthyl, said anthryl
includes 1-anthryl, 2-anthryl and 9-anthryl and said fluorenyl
includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and
9-fluorenyl. The term "heteroaryl" refers to an aryl having 1 to 4
heteroatoms selected from the group consisting of B, N, O, S,
P(.dbd.O), Si and P, and carbon atoms as remaining ring backbone
atoms other than said heteroatom; is a monocyclic ring or fused
ring condensed with at least one benzene ring; may be partially
saturated; may be one formed by linking at least one heteroaryl
group to other heteroaryl or aryl group via one or more single
bonds; may be a divalent aryl group whose ring backbone heteroatom
is oxidized or quaternarized, for example, to form an N-oxide or a
quaternary salt; 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., a
fused ring-type heteroaryl including benzofuranyl, benzothiophenyl,
isobenzofuranyl, benzoimidazolyl, benzothiazolyl,
benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl,
indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl,
cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl,
phenanthridinyl, benzodioxolyl, dibenzofuranyl, dibenzothiophenyl,
etc., N-oxides thereof (for example, pyridyl N-oxide, quinolyl
N-oxide), and quaternary salts thereof.
[0023] In some embodiments of the present disclosure, each of
R.sub.1 to R.sub.12 may independently be further substituted with
at least one selected from the group consisting of deuterium,
chloro, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl,
i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl,
2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl,
perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl,
phenyl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl,
chrysenyl, naphthacenyl, perylenyl, fluorotrimethylsilyl,
triethylsilyl, tripropylsilyl, tri(t-butyl)silyl,
t-butyldimethylsilyl, dimethylphenylsilyl, carbazolyl and
triphenylsilyl, and more preferably at least one selected from the
group consisting of deuterium, chloro, fluoro, methyl, ethyl,
n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl,
n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl and decyl.
[0024] In some embodiments of the present disclosure, an organic
electroluminescent device comprises: an anode, a cathode, and at
least an emitting layer and an electron-transporting layer provided
between the anode and the cathode; the emitting layer containing a
host material which is the organic electroluminescent compound
represented by the following formula (I):
##STR00004## [0025] wherein [0026] R.sub.1, R.sub.2, R.sub.3 and
R.sub.4 each independently represents a substituted or
unsubstituted (C6-C30) aryl group, a substituted or unsubstituted
3- to 30- membered heteroaryl group, --NR.sub.5R.sub.6,
--SiR.sub.7R.sub.8R.sub.9, a cyano group, a nitro group, or a
hydroxyl group; [0027] R.sub.5 to R.sub.11 each independently
represents hydrogen, deuterium, a halogen, a substituted or
unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted
(C6-C30) aryl group, or a substituted or unsubstituted 3- to
30-membered heteroaryl group; or is linked to one or more adjacent
substituents to form a mono- or polycyclic, alicyclic or aromatic
ring whose carbon atom(s) may be replaced by at least one atom
selected from nitrogen, oxygen and sulfur; [0028] a and c each
independently represents an integer of 1 to 3; wherein a or c is an
integer of 1 or more, and each of R.sub.1 or each of R.sub.3 is the
same or different; [0029] b and d each independently represents an
integer of 1 to 3; wherein b or d is an integer of 1 or more, each
of R.sub.2 or each of R.sub.4 is the same or different; and wherein
the heteroaryl group contains at least one atom selected from B, N,
O, S, P(.dbd.O), Si and P.
[0030] In some embodiments of the present disclosure, an organic
electroluminescent device comprises: an anode, a cathode, and at
least an emitting layer and an electron-transporting layer provided
between the anode and the cathode; the emitting layer containing a
host material which is the organic electroluminescent compound
represented by the following formula (II):
##STR00005## [0031] wherein R.sub.1 to R.sub.12 each independently
represents hydrogen, deuterium, a halogen, a substituted or
unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted
(C6-C30) aryl group, or a substituted or unsubstituted 3- to
30-membered heteroaryl group; or is linked to one or more adjacent
substituents to form a mono- or polycyclic, alicyclic or aromatic
ring whose carbon atom(s) may be replaced by at least one atom
selected from nitrogen, oxygen and sulfur.
[0032] In some embodiments of the present disclosure, in an organic
electroluminescent (EL) device comprising at least the emitting
layer and an electron-transporting layer provided between a cathode
and an anode, an emitting layer contains a host material which
includes the organic electroluminescent compounds represented by
the above-depicted formula I or (II).
[0033] FIG. 1 illustrates an example of the organic EL device
according to some embodiments of the present invention. An organic
EL device 10 has a configuration in which an anode 200, a
hole-injecting layer 300, a hole-transporting layer 400, an
emitting layer 500. an electron-transporting layer 600, an
electron-injecting layer 700, and a cathode 800 are stacked on a
substrate 100 in an order. In some embodiments, the emitting layer
500 contains a host material of the organic electroluminescent
compound represented by the above-depicted formula (I). In some
embodiments, the emitting layer 500 contains a host material of the
organic electroluminescent compound represented by the
above-depicted formula (II).
[0034] In some embodiments of the present disclosure, the organic
EL device is an under surface emission type or bottom emission type
where light is out through a substrate. In some embodiments, the
organic EL device of the present disclosure is formed on a
transparent substrate. In some embodiments, the transparent
substrate is a substrate for supporting the organic EL device, and
is preferably a flat and smooth substrate having a light ray
transmittance of 50% or more. In some embodiments, the organic EL
device is an upper surface emission type or top emission type where
light is out from the upper part of the device, and a
light-reflecting metal such as aluminum is provided on the above
substrate.
[0035] In some embodiments of the present disclosure, in the
organic electroluminescent device, 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 some embodiments,
the electron transport compound is reduced to an anion, thus
facilitating injection and transport of electrons from the mixed
region to the electroluminescent medium. In some embodiments, the
hole transport compound is oxidized to a cation, thus facilitating
injection and transport of holes from the mixed region to the
electroluminescent medium. In some embodiments, the oxidative
dopant includes various Lewis acids and acceptor compounds, wherein
the reductive dopant includes alkali metals, alkali metal
compounds, alkaline earth metals, rare-earth metals, or mixtures
thereof. In some embodiments, 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 a white light.
[0036] In some embodiments of the present disclosure, the organic
EL device comprises a first electrode, a second electrode and at
least one organic layer between the first electrode and the second
electrode. In some embodiments, the organic layer comprises a
light-emitting layer. In some embodiments, the light-emitting layer
comprises a composition for the organic electroluminescent device
of the present disclosure and a phosphorous dopant. In some
embodiments, the composition for the organic electroluminescent
device comprises a host material.
[0037] In some embodiments of the present disclosure, the organic
EL device may further comprise at least one compound selected from
the group consisting of arylamine-based compounds and
styrylarylamine-based compounds in the organic layer.
[0038] In some embodiments of the present disclosure, in the
organic EL device, the organic layer may further comprise the
organic electroluminescent compounds represented by the formulas
(I) and (II), 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 metals. In some
embodiments, the organic layer may further comprise a
light-emitting layer and a charge-generating layer.
[0039] In some embodiments of the present disclosure, the organic
EL device may emit a white light by further comprising at least one
light-emitting layer which comprises a blue electroluminescent
compound, a red electroluminescent compound or a green
electroluminescent compound, in addition to the compound of the
present disclosure. In some embodiments, the organic EL device may
further comprise a yellow light-emitting layer or an orange
light-emitting layer.
[0040] In some embodiments of the present disclosure, in the
organic EL device, at least one layer (referred to as "a surface
layer") selected from a chalcogenide layer, a metal-halide layer
and a metal-oxide layer may be placed on one or more inner surfaces
of one or both electrodes. In some embodiments, it is preferred
that the chalcogenide (including oxides) layer of silicon or
aluminum is placed on an anode surface of an electroluminescent
medium layer, and the metal-halide layer or metal-oxide layer is
placed on a cathode surface of an electroluminescent medium layer.
Such a surface layer provides operational 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.
[0041] In some embodiments of the present disclosure, the use of an
organic electroluminescent compound represented by the formula (I)
or (H) as a host material in an organic EL device can provide an
organic EL device with a practical efficiency and lifetime.
[0042] The foregoing outlines features of several embodiments so
that those skilled in the art may better understand the aspects of
the present disclosure. Those skilled in the art should appreciate
that they may readily use the present disclosure as a basis for
designing or modifying other processes and structures for carrying
out the same purposes and/or achieving the same advantages of the
embodiments introduced herein. Those skilled in the art should also
realize that such equivalent constructions do not depart from the
spirit and scope of the present disclosure, and that they may make
various changes, substitutions, and alterations herein without
departing from the spirit and scope of the present disclosure.
* * * * *