U.S. patent application number 17/617263 was filed with the patent office on 2022-07-28 for compound and organic light-emitting device comprising same.
The applicant listed for this patent is LG CHEM, LTD.. Invention is credited to Ji Young Choi, Jae Seung Ha, Wanpyo Hong, Hoon Jun Kim, Joo Ho Kim, Seonwoo Kim, Hojung Lee, Woochul Lee.
Application Number | 20220238817 17/617263 |
Document ID | / |
Family ID | |
Filed Date | 2022-07-28 |
United States Patent
Application |
20220238817 |
Kind Code |
A1 |
Lee; Hojung ; et
al. |
July 28, 2022 |
COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME
Abstract
A compound of Chemical Formula 1: ##STR00001## and an organic
light emitting device including the same.
Inventors: |
Lee; Hojung; (Daejeon,
KR) ; Hong; Wanpyo; (Daejeon, KR) ; Ha; Jae
Seung; (Daejeon, KR) ; Choi; Ji Young;
(Daejeon, KR) ; Lee; Woochul; (Daejeon, KR)
; Kim; Joo Ho; (Daejeon, KR) ; Kim; Hoon Jun;
(Daejeon, KR) ; Kim; Seonwoo; (Daejeon,
KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
LG CHEM, LTD. |
Seoul |
|
KR |
|
|
Appl. No.: |
17/617263 |
Filed: |
January 20, 2021 |
PCT Filed: |
January 20, 2021 |
PCT NO: |
PCT/KR2021/095019 |
371 Date: |
December 7, 2021 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C07D 307/77 20060101 C07D307/77; C09K 11/06 20060101
C09K011/06 |
Foreign Application Data
Date |
Code |
Application Number |
Jan 21, 2020 |
KR |
10-2020-0007825 |
Claims
1. A compound of the following Chemical Formula 1: ##STR00219##
wherein in Chemical Formula 1, L1 is a direct bond or a substituted
or unsubstituted arylene group, D is deuterium, n1 is an integer of
0 to n2 is an integer of 0 to 8 n3 is an integer of 0 to and
1<n1+n2+n3<24.
2. The compound of claim 1, wherein the compound of Chemical
Formula 1 is a compound of the following Chemical Formula 1-1:
##STR00220## in Chemical Formula 1-1, L1, D and n1 to n3 are the
same as defined in claim 1.
3. The compound of claim 1, wherein the compound of Chemical
Formula 1 is any one of compounds of the following Chemical
Formulae 1-2 to 1-5: ##STR00221## ##STR00222## in Chemical Formulae
1-2 to 1-5, L1, D and n1 to n3 are the same as defined in claim
1.
4. The compound of claim 1, wherein L1 is a direct bond; or a
monocyclic or polycyclic arylene group having 6 to 30 carbon atoms
unsubstituted or substituted with deuterium.
5. The compound of claim 1, wherein the compound of Chemical
Formula 1 is any one selected from the following compounds:
##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##
##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312##
##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317##
##STR00318##
6. An organic light emitting device comprising: a first electrode;
a second electrode provided opposite to the first electrode; and an
organic material layer including one or more layers provided
between the first electrode and the second electrode, wherein one
or more layers of the organic material layer include the compound
of claim 1.
7. The organic light emitting device of claim 6, wherein the
organic material layer includes a hole injection layer, a hole
transfer layer or an electron blocking layer, and the hole
injection layer, the hole transfer layer or the electron blocking
layer includes the compound.
8. The organic light emitting device of claim 6, wherein the
organic material layer includes a light emitting layer, and the
light emitting layer includes the compound.
9. The organic light emitting device of claim 6, wherein the
organic material layer includes a light emitting layer, and the
light emitting layer includes the compound as a host of the light
emitting layer.
10. The organic light emitting device of claim 9, wherein the light
emitting layer includes a dopant, and the dopant includes one or
more selected from the group consisting of a fluorescent dopant, a
phosphorescent dopant and a thermal delayed fluorescence-based
dopant.
11. The organic light emitting device of claim 10, wherein the
fluorescent dopant includes one or more selected from the group
consisting of an arylamine-based compound and a boron-based
compound.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a National Stage Application of
International Application No. PCT/KR2021/095019 filed on Jan. 20,
2021, which claims priority to and the benefits of Korean Patent
Application No. 10-2020-0007825, filed with the Korean Intellectual
Property Office on Jan. 21, 2020, the disclosures of which are
incorporated herein by reference in their entirety.
FIELD OF DISCLOSURE
[0002] The present specification relates to a compound, and an
organic light emitting device including the same.
BACKGROUND
[0003] An organic light emission phenomenon generally refers to a
phenomenon converting electrical energy to light energy using an
organic material. An organic light emitting device using an organic
light emission phenomenon normally has a structure including an
anode, a cathode, and an organic material layer therebetween.
Herein, the organic material layer is often formed in a multilayer
structure formed with different materials in order to increase
efficiency and stability of the organic light emitting device, and
for example, may be formed with a hole injection layer, a hole
transfer layer, a light emitting layer, an electron transfer layer,
an electron injection layer and the like. When a voltage is applied
between the two electrodes in such an organic light emitting device
structure, holes and electrons are injected to the organic material
layer from the anode and the cathode, respectively, and when the
injected holes and electrons meet, excitons are formed, and light
emits when these excitons fall back to the ground state.
[0004] Development of new materials for such an organic light
emitting device has been continuously required.
SUMMARY
[0005] The present specification is directed to providing a
compound, and an organic light emitting device including the
same.
[0006] One embodiment of the present specification provides a
compound of the following Chemical Formula 1.
##STR00002##
[0007] In Chemical Formula 1,
[0008] L1 is a direct bond; or a substituted or unsubstituted
arylene group,
[0009] D is deuterium,
[0010] n1 is an integer of 0 to 9,
[0011] n2 is an integer of 0 to 8,
[0012] n3 is an integer of 0 to 7, and
[0013] 1.ltoreq.n1+n2+n3.ltoreq.24.
[0014] Another embodiment of the present specification provides an
organic light emitting device including a first electrode; a second
electrode provided opposite to the first electrode; and an organic
material layer including one or more layers provided between the
first electrode and the second electrode, where one or more layers
of the organic material layer include the compound.
Advantageous Effects
[0015] A compound described in the present specification can be
used as a material of an organic material layer of an organic light
emitting device. A compound according to another embodiment is
capable of enhancing efficiency, lowering a driving voltage and/or
enhancing lifetime properties in an organic light emitting
device.
DESCRIPTION OF DRAWINGS
[0016] FIG. 1 to FIG. 3 each illustrate an example of an organic
light emitting device according to one embodiment of the present
specification.
DESCRIPTION OF REFERENCE NUMERALS
[0017] 1: Substrate
[0018] 2: First Electrode
[0019] 3: Second Electrode
[0020] 4: Light Emitting Layer
[0021] 5: Hole Injection Layer
[0022] 5-1: First Hole Injection Layer
[0023] 5-2: Second Hole Injection Layer
[0024] 6: Hole Transfer Layer
[0025] 6-1: First Hole Transfer Layer
[0026] 6-2: Second Hole Transfer Layer
[0027] 7: Electron Blocking Layer
[0028] 8: Electron Transfer Layer
[0029] 8-1: First Electron Transfer Layer
[0030] 8-2: Second Electron Transfer Layer
[0031] 9: Electron Injection Layer
DETAILED DESCRIPTION
[0032] Hereinafter, the present specification will be described in
more detail.
[0033] One embodiment of the present specification provides a
compound of Chemical Formula 1.
[0034] Chemical Formula 1 according to one embodiment of the
present specification includes 1) a naphthyl group and 2)
benzonaphthofuran bonding through L1 as substituents in the
anthracene core, and Chemical Formula 1 has a structure in which at
least one hydrogen at a substitutable position is substituted with
deuterium, and therefore, has structural properties of enhancing
electron and hole mobility and improving molecular stability.
Accordingly, an organic light emitting device including the same is
superior in terms of driving voltage, efficiency and lifetime.
[0035] Examples of substituents in the present specification are
described below, however, the substituents are not limited
thereto.
[0036] In the present specification,
##STR00003##
means a linking site.
[0037] The term "substitution" means a hydrogen atom bonding to a
carbon atom of a compound being changed to another substituent, and
the position of substitution is not limited as long as it is a
position at which the hydrogen atom is substituted, that is, a
position at which a substituent can substitute, and when two or
more substituents substitute, the two or more substituents may be
the same as or different from each other.
[0038] In the present specification, a term "substituted or
unsubstituted" means being substituted with one or more
substituents selected from the group consisting of deuterium; a
halogen group; a hydroxyl group; a cyano group; a nitro group; an
alkyl group; a cycloalkyl group; an alkoxy group; an alkenyl group;
a haloalkyl group; a silyl group; a boron group; an amine group; an
aryl group; and a heteroaryl group, or being substituted with a
substituent linking two or more substituents among the substituents
illustrated above, or having no substituents.
[0039] In the present specification, linking two or more
substituents refers to linking hydrogen of any one substituent to
another substituent. For example, linking two or more substituents
may include a phenyl group and a naphthyl group being linked to
become a substituent of
##STR00004##
[0040] In addition, linking three substituents includes not only
continuously linking (substituent 1)-(substituent 2)-(substituent
3), but also linking (substituent 2) and (substituent 3) to
(substituent 1). For example, a phenyl group, a naphthyl group and
an isopropyl group may be linked to become a substituent of
##STR00005##
[0041] The same rule described above applies to cases of linking
four or more substituents.
[0042] In the present specification, examples of the halogen group
may include fluorine, chlorine, bromine or iodine.
[0043] In the present specification, the alkyl group may be linear
or branched, and although not particularly limited thereto, the
number of carbon atoms is preferably from 1 to 30.
[0044] Specific examples thereof may include methyl, ethyl, propyl,
n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl,
sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl,
isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl,
2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl,
heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl,
cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl,
2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl,
1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl,
4-methylhexyl, 5-methylhexyl and the like, but are not limited
thereto.
[0045] In the present specification, the cycloalkyl group is not
particularly limited, but preferably has 3 to 30 carbon atoms.
Specific examples thereof may include cyclopropyl, cyclobutyl,
cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl,
cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl,
2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl,
4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, an adamantyl group
and the like, but are not limited thereto.
[0046] In the present specification, the alkoxy group may be
linear, branched or cyclic. The number of carbon atoms of the
alkoxy group is not particularly limited, but is preferably from 1
to 30. Specific examples thereof may include methoxy, ethoxy,
n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy,
sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy,
3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy,
n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not
limited thereto.
[0047] In the present specification, the alkenyl group may be
linear or branched, and although not particularly limited thereto,
the number of carbon atoms is preferably from 2 to 30.
[0048] Specific examples thereof may include vinyl, 1-propenyl,
isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl,
2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl,
1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl,
2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl,
2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl
group and the like, but are not limited thereto.
[0049] In the present specification, the haloalkyl group means, in
the definition of the alkyl group, hydrogen of the alkyl group
being substituted with at least one halogen group.
[0050] In the present specification, the aryl group is not
particularly limited, but preferably has 6 to 30 carbon atoms, and
the aryl group may be monocyclic or polycyclic.
[0051] When the aryl group is a monocyclic aryl group, the number
of carbon atoms is not particularly limited, but is preferably from
6 to 30. Specific examples of the monocyclic aryl group may include
a phenyl group, a biphenyl group, a terphenyl group and the like,
but are not limited thereto.
[0052] When the aryl group is a polycyclic aryl group, the number
of carbon atoms is not particularly limited, but is preferably from
10 to 30. Specific examples of the polycyclic aryl group may
include a naphthyl group, an anthracene group, a phenanthrene
group, a triphenylene group, a pyrene group, a phenalene group, a
perylene group, a chrysene group, a fluorene group and the like,
but are not limited thereto.
[0053] In the present specification, the fluorene group may be
substituted, and adjacent groups may bond to each other to form a
ring.
[0054] When the fluorene group is substituted,
##STR00006##
and the like may be included, however, the structure is not limited
thereto.
[0055] In the present specification, an "adjacent" group may mean a
substituent substituting an atom directly linked to an atom
substituted by the corresponding substituent, a substituent
sterically most closely positioned to the corresponding
substituent, or another substituent substituting an atom
substituted by the corresponding substituent. For example, two
substituents substituting ortho positions in a benzene ring, and
two substituents substituting the same carbon in an aliphatic ring
may be interpreted as groups "adjacent" to each other.
[0056] In the present specification, the heteroaryl group is a
group including one or more atoms that are not carbon, that is,
heteroatoms, and specifically, the heteroatom may include one or
more atoms selected from the group consisting of O, N, Se, S and
the like. The number of carbon atoms is not particularly limited,
but is preferably from 2 to 30, and the heteroaryl group may be
monocyclic or polycyclic. Examples of the heteroaryl group may
include a thiophene group, a furan group, a pyrrole group, an
imidazole group, a thiazole group, an oxazole group, an oxadiazole
group, a pyridine group, a bipyridine group, a pyrimidine group, a
triazine group, a triazole group, an acridine group, a pyridazine
group, a pyrazine group, a quinoline group, a quinazoline group, a
quinoxaline group, a phthalazine group, a pyridopyrimidine group, a
pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline
group, an indole group, a carbazole group, a benzoxazole group, a
benzimidazole group, a benzothiazole group, a benzocarbazole group,
a benzothiophene group, a dibenzothiophene group, a benzofuran
group, a phenanthridine group, a phenanthroline group, an isoxazole
group, a thiadiazole group, a dibenzofuran group, dibenzosilole
group, a phenoxanthine group, a phenoxazine group, a phenothiazine
group, a dihydroindenocarbazole group, a spirofluorenexanthene
group, a spirofluorenethioxanthene group and the like, but are not
limited thereto.
[0057] In the present specification, the silyl group may be an
alkylsilyl group, an arylsilyl group, a heteroarylsilyl group or
the like. As the alkyl group in the alkylsilyl group, the examples
of the alkyl group described above may be applied, and as the aryl
group in the arylsilyl group, the examples of the aryl group
described above may be applied, and as the heteroaryl group in the
heteroarylsilyl group, the examples of the heteroaryl group may be
applied.
[0058] In the present specification, the boron group may be
--BR.sub.100R.sub.101. R.sub.100 and R.sub.101 are the same as or
different from each other, and may be each independently selected
from the group consisting of hydrogen; deuterium; halogen; a
nitrile group; a substituted or unsubstituted monocyclic or
polycyclic cycloalkyl group having 3 to 30 carbon atoms; a
substituted or unsubstituted linear or branched alkyl group having
1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or
polycyclic aryl group having 6 to 30 carbon atoms; and a
substituted or unsubstituted monocyclic or polycyclic heteroaryl
group having 2 to 30 carbon atoms. Specific examples of the boron
group may include a trimethylboron group, a triethylboron group, a
t-butyldimethylboron group, a triphenylboron group, a phenylboron
group and the like, but are not limited thereto.
[0059] In the present specification, the amine group may be
selected from the group consisting of --NH.sub.2, an alkylamine
group, an N-alkylarylamine group, an arylamine group, an
N-arylheteroarylamine group, an N-alkylheteroarylamine group and a
heteroarylamine group, and although not particularly limited
thereto, the number of carbon atoms is preferably from 1 to 30.
Specific examples of the amine group may include a methylamine
group, a dimethylamine group, an ethylamine group, a diethylamine
group, a phenylamine group, a naphthylamine group, a biphenylamine
group, an anthracenylamine group, a 9-methyl-anthracenylamine
group, a diphenylamine group, a ditolylamine group, an
N-phenyltolylamine group, a triphenylamine group, an
N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an
N-biphenylnaphthylamine group, an N-naphthylfluorenylamine group,
an N-phenylphenanthrenylamine group, an
N-biphenylphenanthrenylamine group, an N-phenylfluorenylamine
group, an N-phenylterphenylamine group, an
N-phenanthrenylfluorenylamine group, an N-biphenylfluorenylamine
group and the like, but are not limited thereto.
[0060] In the present specification, the N-alkylarylamine group
means an amine group in which N of the amine group is substituted
with an alkyl group and an aryl group. The alkyl group and the aryl
group in the N-alkylarylamine group are the same as the examples of
the alkyl group and the aryl group described above.
[0061] In the present specification, the N-arylheteroarylamine
group means an amine group in which N of the amine group is
substituted with an aryl group and a heteroaryl group. The aryl
group and the heteroaryl group in the N-arylheteroarylamine group
are the same as the examples of the aryl group and the heteroaryl
group described above.
[0062] In the present specification, the N-alkylheteroarylamine
group means an amine group in which N of the amine group is
substituted with an alkyl group and a heteroaryl group. The alkyl
group and the heteroaryl group in the N-alkylheteroarylamine group
are the same as the examples of the alkyl group and the heteroaryl
group described above. In the present specification, examples of
the alkylamine group include a substituted or unsubstituted
monoalkylamine group, or a substituted or unsubstituted
dialkylamine group. The alkyl group in the alkylamine group may be
a linear or branched alkyl group. The alkylamine group including
two or more alkyl groups may include linear alkyl groups, branched
alkyl groups, or both linear alkyl groups and branched alkyl
groups. For example, the alkyl group in the alkylamine group may be
selected from among the examples of the alkyl group described
above.
[0063] In the present specification, examples of the arylamine
group include a substituted or unsubstituted monoarylamine group,
or a substituted or unsubstituted diarylamine group. The aryl group
in the arylamine group may be a monocyclic aryl group or a
polycyclic aryl group. The arylamine group including two or more
aryl groups may include monocyclic aryl groups, polycyclic aryl
groups, or both monocyclic aryl groups and polycyclic aryl groups.
For example, the aryl group in the arylamine group may be selected
from among the examples of the aryl group described above.
[0064] In the present specification, examples of the
heteroarylamine group include a substituted or unsubstituted
monoheteroarylamine group, or a substituted or unsubstituted
diheteroarylamine group. The heteroarylamine group including two or
more heteroaryl groups may include monocyclic heteroaryl groups,
polycyclic heteroaryl groups, or both monocyclic heteroaryl groups
and polycyclic heteroaryl groups. For example, the heteroaryl group
in the heteroarylamine group may be selected from among the
examples of the heteroaryl group described above.
[0065] In the present specification, the arylene group means the
aryl group having two bonding sites, that is, a divalent group. The
descriptions on the aryl group provided above may be applied
thereto except for those that are each a divalent group.
[0066] In the present specification, "deuteration" or "deuterated"
means that hydrogen at a substitutable position of a compound is
substituted with deuterium.
[0067] In the present specification, "perdeuterated" means a
compound or a group in which all hydrogens in the molecule are
substituted with deuterium, and has the same meaning as "100%
deuterated".
[0068] In the present specification, "X% deuterated", "degree of
deuteration of X%" or "deuterium substitution rate of X%" means
that, in the corresponding structure, X% of hydrogens at
substitutable positions are substituted with deuterium. For
example, when the corresponding structure is dibenzofuran, the
dibenzofuran being "25% deuterated", the dibenzofuran having a
"degree of deuteration of 25%", or the dibenzofuran having a
"deuterium substitution rate of 25%" means that two of eight
hydrogens at substitutable positions of the dibenzofuran are
substituted with deuterium.
[0069] In the present specification, the degree of deuteration may
be identified using known methods such as nuclear magnetic
resonance spectroscopy (1H NMR), TLC/MS (thin-layer
chromatography/mass spectrometry) or MALDI-TOF MS (matrix assisted
laser desorption/ionization time-of-flight mass spectrometry).
[0070] Unless defined otherwise in the present specification, all
technological and scientific terms used in the present
specification have the same meanings as terms commonly understood
by those skilled in the art. Although methods and materials similar
or equivalent to those described in the present specification may
be used in implementing or experimenting embodiments of the present
disclosure, suitable methods and materials are described later. All
publications, patent applications, patents and other reference
documents mentioned in the present specification are incorporated
by reference in the present specification as a whole, and when
conflicting, the present specification including definitions has
priority unless specific passage is mentioned. Furthermore,
materials, methods and examples are for illustrative purposes only,
and not to limit the present specification. According to one
embodiment of the present specification, 0 in the definition of n1
to n3 means that hydrogen bonds instead of deuterium.
[0071] According to one embodiment of the present specification,
the compound of Chemical Formula 1 may be a compound of the
following Chemical Formula 1-1.
##STR00007##
[0072] In Chemical Formula 1-1, L1, D and n1 to n3 have the same
definitions as in Chemical Formula 1.
[0073] According to one embodiment of the present specification,
the compound of Chemical Formula 1 may be any one of compounds of
the following Chemical Formulae 1-2 to 1-5.
##STR00008## ##STR00009##
[0074] In Chemical Formulae 1-2 to 1-5,
[0075] L1, D and n1 to n3 have the same definitions as in Chemical
Formula 1.
[0076] According to one embodiment of the present specification,
the compound of Chemical Formula 1 may be a compound of the
following Chemical Formula 1-6 or 1-7.
##STR00010##
[0077] In Chemical Formulae 1-6 and 1-7, L1, D and n1 to n3 have
the same definitions as in Chemical Formula 1.
[0078] According to one embodiment of the present specification,
the compound of Chemical Formula 1 is a compound of the following
Chemical Formula 1-8 or 1-9.
##STR00011##
[0079] In Chemical Formulae 1-8 and 1-9, D and n1 to n3 have the
same definitions as in Chemical Formula 1, and
[0080] L11 is a substituted or unsubstituted arylene group.
[0081] According to one embodiment of the present specification, L1
is a direct bond; or a substituted or unsubstituted monocyclic or
polycyclic arylene group having 6 to 30 carbon atoms.
[0082] According to one embodiment of the present specification, L1
is a direct bond; or a substituted or unsubstituted monocyclic or
polycyclic arylene group having 6 to 20 carbon atoms.
[0083] According to one embodiment of the present specification, L1
is a direct bond; or a substituted or unsubstituted monocyclic or
polycyclic arylene group having 6 to 10 carbon atoms.
[0084] According to one embodiment of the present
specification,
[0085] L1 is a direct bond; or an arylene group unsubstituted or
substituted with deuterium.
[0086] According to one embodiment of the present specification, L1
is a direct bond; or a monocyclic or polycyclic arylene group
having 6 to 30 carbon atoms unsubstituted or substituted with
deuterium.
[0087] According to one embodiment of the present specification, L1
is a direct bond; or a monocyclic or polycyclic arylene group
having 6 to 20 carbon atoms unsubstituted or substituted with
deuterium.
[0088] According to one embodiment of the present specification, L1
is a direct bond; or a monocyclic or polycyclic arylene group
having 6 to 10 carbon atoms unsubstituted or substituted with
deuterium.
[0089] According to one embodiment of the present specification, L1
is a direct bond; a phenylene group unsubstituted or substituted
with deuterium; or a naphthylene group unsubstituted or substituted
with deuterium.
[0090] According to one embodiment of the present specification, L1
is a direct bond.
[0091] According to one embodiment of the present specification, L1
is a phenylene group.
[0092] According to one embodiment of the present specification, L1
is a naphthylene group.
[0093] According to one embodiment of the present specification, L1
is a phenylene group substituted with deuterium.
[0094] According to one embodiment of the present specification, L1
is a naphthylene group substituted with deuterium.
[0095] According to one embodiment of the present specification,
the compound of Chemical Formula 1 is a compound of the following
Chemical Formula 1-10 or 1-11.
##STR00012##
[0096] In Chemical Formulae 1-10 and 1-11,
[0097] D and n1 to n3 have the same definitions as in Chemical
Formula 1,
[0098] n4 is an integer of 0 to 4, and
[0099] n5 is an integer of 0 to 6.
[0100] According to one embodiment of the present specification,
the compound of Chemical Formula 1 is any one selected from
compounds of the following structural formulae.
##STR00013## ##STR00014## ##STR00015##
[0101] In the structural formulae,
[0102] L1 and D have the same definitions as in Chemical Formula
1,
[0103] n11 is an integer of 1 to 9,
[0104] n12 is an integer of 1 to 8, and
[0105] n13 is an integer of 1 to 7.
[0106] According to one embodiment of the present specification,
the compound of Chemical Formula 1 is any one selected from
compounds of the following structural formulae.
##STR00016## ##STR00017## ##STR00018##
[0107] In the structural formulae,
[0108] D has the same definition as in Chemical Formula 1,
[0109] n11 is an integer of 1 to 9,
[0110] n12 is an integer of 1 to 8, and
[0111] n13 is an integer of 1 to 7.
[0112] According to one embodiment of the present specification,
the compound of Chemical Formula 1 is any one selected from
compounds of the following structural formulae.
##STR00019## ##STR00020## ##STR00021## ##STR00022##
[0113] In the structural formulae,
[0114] D has the same definition as in Chemical Formula 1,
[0115] n11 is an integer of 1 to 9,
[0116] n12 is an integer of 1 to 8,
[0117] n13 is an integer of 1 to 7, and
[0118] n14 is an integer of 1 to 4.
[0119] According to one embodiment of the present specification,
the compound of Chemical Formula 1 is any one selected from
compounds of the following structural formulae.
##STR00023## ##STR00024## ##STR00025## ##STR00026##
[0120] In the structural formulae,
[0121] D has the same definition as in Chemical Formula 1,
[0122] n11 is an integer of 1 to 9,
[0123] n12 is an integer of 1 to 8,
[0124] n13 is an integer of 1 to 7, and
[0125] n15 is an integer of 1 to 6.
[0126] According to one embodiment of the present specification, at
least one hydrogen at a substitutable position is substituted with
deuterium in Chemical Formula 1.
[0127] According to one embodiment of the present specification,
Chemical Formula 1 has a deuterium substitution rate of 100%.
[0128] According to one embodiment of the present specification,
Chemical Formula 1 has a deuterium substitution rate of 10% to
90%.
[0129] According to one embodiment of the present specification,
Chemical Formula 1 has a deuterium substitution rate of 20% to
80%.
[0130] According to one embodiment of the present specification,
Chemical Formula 1 has a deuterium substitution rate of 30% to
70%.
[0131] According to one embodiment of the present specification,
Chemical Formula 1 has a deuterium substitution rate of 40% to
60%.
[0132] According to one embodiment of the present specification,
Chemical Formula 1 has a deuterium substitution rate of 50%.
[0133] According to one embodiment of the present specification,
Chemical Formula 1 is any one selected from among the following
compounds.
##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## ##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##
[0134] One embodiment of the present specification provides an
organic light emitting device including the compound described
above.
[0135] In the present specification, a description of a certain
member being placed "on" another member includes not only a case of
the one member being in contact with the another member but a case
of still another member being present between the two members.
[0136] In the present specification, a description of a certain
part "including" certain constituents means capable of further
including other constituents, and does not exclude other
constituents unless particularly stated on the contrary. In the
present specification, the "layer" has a meaning compatible with a
`film` mainly used in the art, and means coating covering a target
area. The size of the "layer" is not limited, and each "layer" may
have the same or a different size. According to one embodiment, the
size of the "layer" may be the same as the whole device, may
correspond to the size of a specific functional area, or may be as
small as a single sub-pixel.
[0137] In the present specification, a meaning of a specific A
material being included in a B layer includes both i) one or more
types of A materials being included in one B layer, and ii) a B
layer being formed in one or more layers, and an A material being
included in one or more of the B layers that is a multilayer.
[0138] In the present specification, a meaning of a specific A
material being included in a C layer or a D layer includes both i)
being included in one or more layers of one or more C layers, ii)
being included in one or more layers of one or more D layers, or
iii) being included in each of one or more C layers and one or more
D layers.
[0139] One embodiment of the present specification provides an
organic light emitting device including a first electrode; a second
electrode provided opposite to the first electrode; and an organic
material layer including one or more layers provided between the
first electrode and the second electrode, wherein one or more
layers of the organic material layer include the compound of
Chemical Formula 1.
[0140] The organic material layer of the organic light emitting
device of the present specification may be formed in a single layer
structure, but may also be formed in a multilayer structure in
which two or more organic material layers are laminated. For
example, the organic light emitting device of the present
specification may have a structure including a hole injection
layer, a hole transfer layer, a light emitting layer, an electron
transfer layer, an electron injection layer, an electron blocking
layer, a hole blocking layer and the like.
[0141] However, the structure of the organic light emitting device
is not limited thereto, and may include a smaller number of organic
layers.
[0142] According to one embodiment of the present specification,
the organic material layer includes a hole injection layer, a hole
transfer layer or an electron blocking layer, and the hole
injection layer, the hole transfer layer or the electron blocking
layer includes the compound.
[0143] According to one embodiment of the present specification,
the organic material layer includes a light emitting layer, and the
light emitting layer includes the compound.
[0144] According to one embodiment of the present specification,
the organic material layer includes a light emitting layer, and the
light emitting layer includes the compound as a host of the light
emitting layer.
[0145] According to one embodiment of the present specification,
the light emitting layer includes a dopant, and the dopant includes
one or more selected from the group consisting of a fluorescent
dopant, a phosphorescent dopant and a thermal delayed
fluorescence-based dopant.
[0146] According to one embodiment of the present specification,
the fluorescent dopant includes one or more selected from the group
consisting of an arylamine-based compound and a boron-based
compound.
[0147] According to one embodiment of the present specification,
the fluorescent dopant is an arylamine-based compound.
[0148] According to one embodiment of the present specification,
the fluorescent dopant is a boron-based compound.
[0149] According to one embodiment of the present specification,
the organic material layer includes a light emitting layer, the
light emitting layer includes a host and a dopant, the host
includes the compound, and the dopant includes one or more selected
from the group consisting of the fluorescent dopant, the
phosphorescent dopant and the thermal delayed fluorescence-based
dopant.
[0150] According to one embodiment of the present specification,
the arylamine-based compound is a compound of the following
Chemical Formula D-1.
##STR00189##
[0151] In Chemical Formula D-1,
[0152] L101 and L102 are the same as or different from each other,
and each independently a direct bond; or a substituted or
unsubstituted arylene group, and
[0153] Ar101 to Ar104 are the same as or different from each other,
and each independently a substituted or unsubstituted aryl group;
or a substituted or unsubstituted heteroaryl group.
[0154] According to one embodiment of the present specification,
L101 and L102 are a direct bond.
[0155] According to one embodiment of the present specification,
Ar101 to Ar104 are the same as or different from each other, and
each independently a substituted or unsubstituted monocyclic or
polycyclic aryl group having 6 to 30 carbon atoms; or a substituted
or unsubstituted monocyclic or polycyclic heteroaryl group having 2
to 30 carbon atoms.
[0156] According to one embodiment of the present specification,
Ar101 to Ar104 are the same as or different from each other, and
each independently a monocyclic or polycyclic aryl group having 6
to 30 carbon atoms unsubstituted or substituted with a linear or
branched alkyl group having 1 to 30 carbon atoms; or a monocyclic
or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to one embodiment of the present specification,
[0157] Ar101 to Ar104 are the same as or different from each other,
and each independently a phenyl group substituted with a methyl
group; or a dibenzofuran group.
[0158] According to one embodiment of the present specification,
the compound of Chemical Formula D-1 is the following compound.
##STR00190##
[0159] According to one embodiment of the present specification,
the boron-based compound is a compound of the following Chemical
Formula D-2.
##STR00191##
[0160] In Chemical Formula D-2,
[0161] T1 to T5 are the same as or different from each other, and
each independently hydrogen; a substituted or unsubstituted alkyl
group; a substituted or unsubstituted amine group; or a substituted
or unsubstituted aryl group,
[0162] t3 and t4 are each an integer of 1 to 4,
[0163] t5 is an integer of 1 to 3,
[0164] when t3 is 2 or greater, the two or more T3s are the same as
or different from each other,
[0165] when t4 is 2 or greater, the two or more T4s are the same as
or different from each other, and
[0166] when t5 is 2 or greater, the two or more T5s are the same as
or different from each other.
[0167] According to one embodiment of the present specification, T1
to T5 are the same as or different from each other, and each
independently hydrogen; a substituted or unsubstituted linear or
branched alkyl group having 1 to 30 carbon atoms; a substituted or
unsubstituted monocyclic or polycyclic arylamine group having 6 to
30 carbon atoms; or a substituted or unsubstituted monocyclic or
polycyclic aryl group having 6 to 30 carbon atoms.
[0168] According to one embodiment of the present specification, T1
to T5 are the same as or different from each other, and each
independently hydrogen; a linear or branched alkyl group having 1
to 30 carbon atoms; a monocyclic or polycyclic arylamine group
having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl
group having 6 to 30 carbon atoms unsubstituted or substituted with
a linear or branched alkyl group having 1 to 30 carbon atoms.
[0169] According to one embodiment of the present specification, T1
to T5 are the same as or different from each other, and each
independently hydrogen; a tert-butyl group; a diphenylamine group;
or a phenyl group unsubstituted or substituted with a tert-butyl
group.
[0170] According to one embodiment of the present specification,
the compound of Chemical Formula D-2 is the following compound.
##STR00192##
[0171] According to one embodiment of the present specification,
those known in the art may be used as the phosphorescent dopant and
the thermal delayed fluorescence-based dopant, however, the
phosphorescent dopant and the thermal delayed fluorescence-based
dopant are not limited thereto.
[0172] According to one embodiment of the present specification,
the light emitting layer includes the host and the dopant in a
weight ratio of 99:1 to 1:99. Specifically, the light emitting
layer includes the host and the dopant in a weight ratio of 99:1 to
50:50, and more specifically in a weight ratio of 99:1 to 95:5.
[0173] According to one embodiment of the present specification,
the organic light emitting device further includes one, two or more
layers selected from the group consisting of a hole injection
layer, a hole transfer layer, a light emitting layer, an electron
transfer layer, an electron injection layer, a hole blocking layer
and an electron blocking layer.
[0174] According to one embodiment of the present specification,
the organic light emitting device includes a first electrode; a
second electrode provided to face the first electrode; a light
emitting layer provided between the first electrode and the second
electrode; and two or more organic material layers provided either
between the light emitting layer and the first electrode or between
the light emitting layer and the second electrode.
[0175] According to one embodiment of the present specification, as
the two or more organic material layers provided either between the
light emitting layer and the first electrode or between the light
emitting layer and the second electrode, two or more may be
selected from the group consisting of a light emitting layer, a
hole transfer layer, a hole injection layer, a hole injection and
transfer layer, an electron blocking layer, a hole blocking layer,
an electron injection layer, an electron transfer layer, and an
electron injection and transfer layer.
[0176] According to one embodiment of the present specification,
two or more hole injection layers are included between the light
emitting layer and the first electrode. The two or more hole
injection layers may include materials the same as or different
from each other.
[0177] According to one embodiment of the present specification,
two or more hole transfer layers are included between the light
emitting layer and the first electrode. The two or more hole
transfer layers may include materials the same as or different from
each other.
[0178] According to one embodiment of the present specification,
two or more electron transfer layers are included between the light
emitting layer and the second electrode. The two or more electron
transfer layers may include materials the same as or different from
each other.
[0179] According to one embodiment of the present specification,
the first electrode is an anode or a cathode.
[0180] According to one embodiment of the present specification,
the second electrode is a cathode or an anode. According to one
embodiment of the present specification, the organic light emitting
device may be an organic light emitting device having a structure
in which an anode, an organic material layer including one or more
layers, and a cathode are consecutively laminated on a substrate
(normal type).
[0181] According to one embodiment of the present specification,
the organic light emitting device may be an organic light emitting
device having a structure in a reverse direction in which a
cathode, an organic material layer including one or more layers,
and an anode are consecutively laminated on a substrate (inverted
type).
[0182] For example, structures of the organic light emitting device
according to one embodiment of the present specification are
illustrated in FIG. 1 to FIG. 3. FIG. 1 to FIG. 3 only illustrate
the organic light emitting device, and the organic light emitting
device is not limited thereto.
[0183] FIG. 1 illustrates a structure of the organic light emitting
device in which a first electrode (2), a light emitting layer (4)
and a second electrode (3) are consecutively laminated on a
substrate (1). The compound of Chemical Formula 1 is included in
the light emitting layer.
[0184] FIG. 2 illustrates a structure of the organic light emitting
device in which a first electrode (2), a hole injection layer (5),
a first hole transfer layer (6-1), a second hole transfer layer
(6-2), a light emitting layer (4), an electron transfer layer (8),
an electron injection layer (9) and a second electrode (3) are
consecutively laminated on a substrate (1). The compound of
Chemical Formula 1 is included in the light emitting layer.
[0185] FIG. 3 illustrates a structure of the organic light emitting
device in which a first electrode (2), a first hole injection layer
(5-1), a second hole injection layer (5-2), a hole transfer layer
(6), an electron blocking layer (7), a light emitting layer (4), a
first electron transfer layer (8-1), a second electron transfer
layer (8-2), an electron injection layer (9) and a second electrode
(3) are consecutively laminated on a substrate (1). The compound of
Chemical Formula 1 is included in the light emitting layer. The
organic light emitting device of the present specification may be
manufactured using materials and methods known in the art, except
that the light emitting layer includes the compound, that is, the
compound of Chemical Formula 1.
[0186] When the organic light emitting device includes a plurality
of organic material layers, the organic material layers may be
formed with the same materials or different materials.
[0187] For example, the organic light emitting device of the
present specification may be manufactured by consecutively
laminating a first electrode, an organic material layer and a
second electrode on a substrate. Herein, the organic light emitting
device may be manufactured by forming an anode on a substrate by
depositing a metal, a metal oxide having conductivity, or an alloy
thereof using a physical vapor deposition (PVD) method such as
sputtering or e-beam evaporation, and forming an organic material
layer including a hole injection layer, a hole transfer layer, a
light emitting layer and an electron transfer layer thereon, and
then depositing a material usable as a cathode thereon. In addition
to such a method, the organic light emitting device may also be
manufactured by consecutively depositing a second electrode
material, an organic material layer and a first electrode material
on a substrate.
[0188] In addition, the compound of Chemical Formula 1 may be
formed into an organic material layer using a solution coating
method as well as a vacuum deposition method when manufacturing the
organic light emitting device. Herein, the solution coating method
means spin coating, dip coating, doctor blading, inkjet printing,
screen printing, a spray method, roll coating and the like, but is
not limited thereto.
[0189] In addition to such a method, the organic light emitting
device may also be manufactured by consecutively laminating a
second electrode material, an organic material layer and a first
electrode material on a substrate. However, the manufacturing
method is not limited thereto.
[0190] As the first electrode material, materials having large work
function are normally preferred so that hole injection to an
organic material layer is smooth. Examples thereof include metals
such as vanadium, chromium, copper, zinc and gold, or alloys
thereof; metal oxides such as zinc oxide, indium oxide, indium tin
oxide (ITO) and indium zinc oxide (IZO); combinations of metals and
oxides such as ZnO:Al or SnO.sub.2:Sb; conductive polymers such as
poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene]
(PEDOT), polypyrrole and polyaniline, but are not limited
thereto.
[0191] As the second electrode material, materials having small
work function are normally preferred so that electron injection to
an organic material layer is smooth. Examples thereof include
metals such as magnesium, calcium, sodium, potassium, titanium,
indium, yttrium, lithium, gadolinium, aluminum, silver, tin and
lead, or alloys thereof; multilayer structure materials such as
LiF/Al or LiO.sub.2/Al, and the like, but are not limited
thereto.
[0192] The light emitting layer may include a host material and a
dopant material. When an additional light emitting layer is
included in addition to the light emitting layer including the
compound of Chemical Formula 1 according to one embodiment of the
present specification, the host material includes fused and/or
non-fused aromatic ring derivatives, heteroring-containing
compounds or the like. Specifically, the fused aromatic ring
derivative includes anthracene derivatives, pyrene derivatives,
naphthalene derivatives, pentacene derivatives, phenanthrene
compounds, fluoranthene compounds and the like, and the
heteroring-containing compound includes dibenzofuran derivatives,
ladder-type furan compounds, pyrimidine derivatives and the like,
however, the material is not limited thereto.
[0193] The dopant material includes aromatic amine derivatives,
styrylamine compounds, boron complexes, fluoranthene compounds,
metal complexes and the like. Specifically, the aromatic amine
derivative is a fused aromatic ring derivative having a substituted
or unsubstituted arylamine group and includes arylamine
group-including pyrene, anthracene, chrysene, peryflanthene and the
like. In addition, the styrylamine compound is a compound in which
substituted or unsubstituted arylamine is substituted with at least
one arylvinyl group, and one, two or more substituents selected
from the group consisting of an aryl group, a silyl group, an alkyl
group, a cycloalkyl group and an arylamine group are substituted or
unsubstituted. Specifically, styrylamine, styryldiamine,
styryltriamine, styryltetramine or the like is included, however,
the styrylamine compound is not limited thereto. In addition, the
metal complex includes iridium complexes, platinum complexes or the
like, but is not limited thereto.
[0194] The hole injection layer is a layer receiving holes from an
electrode. The hole injection material preferably has, by having an
ability to transfer holes, a hole receiving effect from an anode
and an excellent hole injection effect for a light emitting layer
or a light emitting material. In addition, the hole injection
material is preferably a material having an excellent ability to
prevent excitons generated in the light emitting layer from moving
to an electron injection layer or an electron injection material.
In addition, a material having an excellent thin film foaming
ability is preferred. In addition, the highest occupied molecular
orbital (HOMO) of the hole injection material is preferably in
between the work function of an anode material and the HOMO of
surrounding organic material layers. Specific examples of the hole
injection material include metal porphyrins, oligothiophene,
arylamine-based organic materials; hexanitrile
hexaazatriphenylene-based organic materials; quinacridone-based
organic materials; perylene-based organic materials;
polythiophene-based conductive polymers such as anthraquinone or
polyaniline, and the like, but are not limited thereto.
[0195] The hole transfer layer is a layer receiving holes from a
hole injection layer and transferring the holes to a light emitting
layer. As the hole transfer material, materials having, as a
material capable of receiving holes from an anode or a hole
injection layer and moving the holes to a light emitting layer,
high mobility for the holes are preferred. Specific examples
thereof include arylamine-based organic materials, conductive
polymers, block copolymers having conjugated parts and
non-conjugated parts together, and the like, but are not limited
thereto.
[0196] The electron transfer layer is a layer receiving electrons
from an electron injection layer and transferring the electrons to
a light emitting layer. As the electron transfer material,
materials capable of favorably receiving electrons from a cathode,
moving the electrons to a light emitting layer, and having high
mobility for the electrons are preferred. Specific examples thereof
include Al complexes of 8-hydroxyquinoline; complexes including
Alq.sub.3; organic radical compounds; hydroxyflavon-metal complexes
and the like, but are not limited thereto. The electron transfer
layer may be used together with any desired cathode material as
used in the art. Particularly, the suitable cathode material is a
common material having low work function and having an aluminum
layer or a silver layer following. Specifically, cesium, barium,
calcium, ytterbium, samarium and the like are included, and in each
case, an aluminum layer or a silver layer follows.
[0197] The electron injection layer is a layer receiving electrons
from an electrode. As the electron injection material, materials
having an excellent electron transferring ability, having an
electron receiving effect from a second electrode, and having an
excellent electron injection effect for a light emitting layer or
light emitting material are preferred. In addition, materials
preventing excitons generated in the light emitting layer from
moving to a hole injection layer, and having an excellent thin film
forming ability are preferred. Specific examples thereof include
fluorenone, anthraquinodimethane, diphenoquinone, thiopyran
dioxide, oxazole, oxadiazole, triazole, imidazole, perylene
tetracarboxylic acid, fluorenylidene methane, anthrone or the like,
and derivatives thereof, metal complex compounds,
nitrogen-containing 5-membered ring derivatives, and the like, but
are not limited thereto.
[0198] The metal complex compound includes 8-hydroxyquinolinato
lithium, bis(8-hydroxyquinolinato)zinc,
bis(8-hydroxyquinolinato)copper,
bis(8-hydroxyquinolinato)manganese,
tris(8-hydroxyquinolinato)aluminum,
tris(2-methyl-8-hydroxyquinolinato)aluminum,
tris(8-hydroxyquinolinato)gallium,
bis(10-hydroxybenzo[h]quinolinato)beryllium,
bis(10-hydroxybenzo[h]quinolinato)zinc,
bis(2-methyl-8-quinolinato)chlorogallium,
bis(2-methyl-8-quinolinato) (o-cresolato)gallium,
bis(2-methyl-8-quinolinato) (1-naphtholato)aluminum,
bis(2-methyl-8-quinolinato) (2-naphtholato)gallium and the like,
but is not limited thereto. The electron blocking layer is a layer
capable of enhancing lifetime and efficiency of a device by
preventing electrons injected from an electron injection layer from
passing through a light emitting layer and entering a hole
injection layer. Known material may be used without limit, and the
electron blocking layer may be formed between the light emitting
layer and the hole injection layer, between the light emitting
layer and a hole transfer layer, or between the light emitting
layer and a layer carrying out hole injection and hole transfer at
the same time.
[0199] The hole blocking layer is a layer blocking holes from
reaching a cathode, and may be generally formed under the same
condition as the electron injection layer. Specific examples
thereof may include oxadiazole derivatives, triazole derivatives,
phenanthroline derivatives, aluminum complexes and the like, but
are not limited thereto.
[0200] The organic light emitting device according to the present
specification may be a top-emission type, a bottom-emission type or
a dual-emission type depending on the materials used.
[0201] Hereinafter, the present specification will be described in
detail with reference to examples, comparative examples and the
like. However, the examples and the comparative examples according
to the present specification may be modified to various other
forms, and the scope of the present specification is not to be
construed as being limited to the examples and the comparative
examples described below. Examples and comparative examples of the
present specification are provided in order to more fully describe
the present specification to those having average knowledge in the
art.
SYNTHESIS EXAMPLE 1. Synthesis of BH-1
##STR00193##
[0203] <1-a> Preparation of Compound BH-1-a
[0204] 9-(Naphthalen-1-yl)anthracene (23.4 g, 76.9 mmol) and
aluminum chloride (AlCl.sub.3) (5.0 g ,38.4 mmol) were introduced
to C.sub.6D.sub.6 (800 ml), and the mixture was stirred for 3
hours. After the reaction was finished, D.sub.2O (100 ml) was
introduced thereto, the result was stirred for 30 minutes, and
trimethylamine (10 ml) was added dropwise thereto. The reaction
solution was transferred to a separatory funnel, and extracted with
water and toluene. The result was dried with anhydrous magnesium
sulfate, and, after removing the organic solvent under vacuum,
purified using column chromatography to obtain Compound BH-1-a
(18.9 g, yield 77%).
[0205] MS: [M+H]+=321
[0206] <1-b> Preparation of Compound BH-1-b
[0207] After dispersing Compound BH-1-a (15 g, 46.8 mmol) to
dimethylformamide (230 ml), an n-bromosuccinimide (8.4 g, 46.8
mmol) solution dissolved in dimethylformamide (25 ml) was slowly
added dropwise thereto. The result was reacted for 2 hours at room
temperature, and then water (500 ml) was added dropwise thereto.
Produced solids were filtered, dissolved in ethyl acetate,
transferred to a separatory funnel, and washed several times with
distilled water. The result was recrystallized in ethyl acetate to
obtain Compound BH-1-b (13.2 g, yield 72%).
[0208] MS: [M+H]+=399
[0209] <1-c> Preparation of Compound BH-1
[0210] After dissolving Compound BH-1-b (10 g, 25.2 mmol) and
naphtho[2,1-b]benzofuran-11-ylboronic acid (37.6 g, 143.44 mmol) in
tetrahydrofuran (200 ml), an aqueous 2 M K.sub.2CO.sub.3 solution
(40 ml) was introduced thereto. After that, Pd(PPh.sub.3).sub.4
(0.29 g, 0.25 mmol) was introduced thereto, and the result was
refluxed for 3 hours. The reaction solution was cooled, and the
organic layer was extracted with ethyl acetate and then dried with
anhydrous magnesium sulfate. The organic solvent was removed under
vacuum, and the result was purified using column chromatography to
obtain Compound BH-1 (10.1 g, yield 75%).
[0211] MS: [M+H]+=536
SYNTHESIS EXAMPLE 2. Synthesis of BH-2
##STR00194##
[0213] <2-a> Preparation of Compound BH-2-a
[0214] Compound BH-2-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of
Compound BH-1-b.
[0215] MS: [M+H]+=521
[0216] <2-b> Preparation of Compound BH-2
[0217] Compound BH-2 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-2-a was used instead of
9-(naphthalen-1-yl)anthracene.
[0218] MS: [M+H]+=545
SYNTHESIS EXAMPLE 3. Synthesis of BH-3
##STR00195##
[0220] <3-a> Preparation of Compound BH-3-a
[0221] Compound BH-3-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromo-10-(naphthalen-2-yl)anthracene was used instead of
Compound BH-1-b.
[0222] MS: [M+H]+=521
[0223] <3-b> Preparation of Compound BH-3
[0224] Compound BH-3 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-3-a was used instead of 9-(naphthalen-1-yl)
anthracene.
[0225] MS: [M+H]+=545
SYNTHESIS EXAMPLE 4. Synthesis of BH-4
##STR00196## ##STR00197##
[0227] <4-a> Preparation of Compound BH-4-a
[0228] Compound BH-4-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 11-bromonaphtho[2,1-b]benzofuran was used instead of Compound
BH-1-b, and (4-chlorophenyl)boronic acid was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0229] MS: [M+H]+=329
[0230] <4-b> Preparation of Compound BH-4-b
[0231] Compound BH-4-a (30 g, 91.2 mmol), bis(pinacolato)diboron
(34.7 g, 136.8 mmol), tricyclohexylphosphine (1.0 g, 3.64 mmol),
potassium acetate (26.9 g, 273.6 mmol) and Pd(dba)2 (1.0 g, 1.82
mmol) were introduced to 1,4-dioxane (450 ml) and the mixture was
refluxed for 4 hours. The reaction solution was cooled, and the
organic layer was extracted with ethyl acetate and then dried with
anhydrous magnesium sulfate. The organic solvent was removed under
vacuum, and the result was purified using column chromatography to
obtain Compound BH-4-b (27.9 g, yield 73%).
[0232] MS: [M+H]+=421
[0233] <4-c> Preparation of Compound BH-4-c
[0234] Compound BH-4-c was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of
Compound BH-1-b, and Compound BH-4-b was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0235] MS: [M+H]+=597
[0236] <4-d> Preparation of Compound BH-4
[0237] Compound BH-4 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-4-c was used instead of 9-(naphthalen-1-yl)
anthracene.
[0238] MS: [M+H]+=625
SYNTHESIS EXAMPLE 5. Synthesis of BH-5
##STR00198##
[0240] <5-a> Preparation of Compound BH-5-a
[0241] Compound BH-5-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that 9-(naphthalen-2-yl)anthracene was used instead of
9-(naphthalen-1-yl)anthracene.
[0242] MS: [M+H]+=321
[0243] <5-b> Preparation of Compound BH-5-b
[0244] Compound BH-5-b was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-b except
that Compound BH-5-a was used instead of Compound BH-1-a.
[0245] MS: [M+H]+=398
[0246] <5-c> Preparation of Compound BH-5
[0247] Compound BH-5 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that Compound BH-5-b was used instead of Compound BH-1-b, and
naphtho[2,1-b]benzofuran-10-ylboronic acid was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0248] MS: [M+H]+=536
SYNTHESIS EXAMPLE 6. Synthesis of BH-6
##STR00199##
[0250] <6-a> Preparation of Compound BH-6-a
[0251] Compound BH-6-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 11-bromonaphtho[2,1-b]benzofuran was used instead of Compound
BH-1-b, and (3-chlorophenyl)boronic acid was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0252] MS: [M+H]+=329
[0253] <6-b> Preparation of Compound BH-6-b
[0254] Compound BH-6-b was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 4-b except
that Compound BH-6-a was used instead of Compound BH-4-a.
[0255] MS: [M+H]+=421
[0256] <6-c> Preparation of Compound BH-6
[0257] Compound BH-6 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that Compound BH-5-b was used instead of Compound BH-1-b, and
Compound BH-6-b was used instead of naphtho[2,1-b]
benzofuran-11-ylboronic acid.
[0258] MS: [M+H]+=612
SYNTHESIS EXAMPLE 7. Synthesis of BH-7
##STR00200##
[0260] <7-a> Preparation of Compound BH-7-a
[0261] Compound BH-7-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of
Compound BH-1-b, and naphtho[2,1-b]benzofuran-10-ylboronic acid was
used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0262] MS: [M+H]+=521
[0263] <7-b> Preparation of Compound BH-7
[0264] Compound BH-7 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-7-a was used instead of 9-(naphthalen-1-yl)
anthracene.
[0265] MS: [M+H]+=545
[0266] Synthesis Example 8. Synthesis of BH-8
##STR00201## ##STR00202##
[0267] <8-a> Preparation of Compound BH-8-a
[0268] Compound BH-8-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 10-bromonaphtho[2,1-b]benzofuran was used instead of Compound
BH-1-b, and (6-chloronaphthalen-2-yl)boronic acid was used instead
of naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0269] MS: [M+H]+=379
[0270] <8-b> Preparation of Compound BH-8-b
[0271] Compound BH-8-b was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 4-b except
that Compound BH-8-a was used instead of Compound BH-4-a.
[0272] MS: [M+H]+=471
[0273] <8-c> Preparation of Compound BH-8-c
[0274] Compound BH-8-c was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that Compound BH-8-b was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid, and
9-bromo-10-(naphthalen-1-yl)anthracene was used instead of Compound
BH-1-b.
[0275] MS: [M+H]+=647
[0276] <8-d> Preparation of Compound BH-8
[0277] Compound BH-8 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-8-c was used instead of 9-(naphthalen-1-yl)
anthracene.
[0278] MS: [M+H]+=677
SYNTHESIS EXAMPLE 9. Synthesis of BH-9
##STR00203## ##STR00204##
[0280] <9-a> Preparation of Compound BH-9-a
[0281] Compound BH-9-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromonaphtho[2,1-b]benzofuran was used instead of Compound
BH-1-b, and (4-chlorophenyl)boronic acid was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0282] MS: [M+H]+=329
[0283] <9-b> Preparation of Compound BH-9-b
[0284] Compound BH-9-b was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 4-b except
that Compound BH-9-a was used instead of Compound BH-4-a.
[0285] MS: [M+H]+=421
[0286] <9-c> Preparation of Compound BH-9-c
[0287] Compound BH-9-c was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that Compound BH-9-b was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid, and
9-bromo-10-(naphthalen-2-yl)anthracene was used instead of Compound
BH-1-b.
[0288] MS: [M+H]+=597
[0289] <9-d> Preparation of Compound BH-9
[0290] Compound BH-9 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-9-c was used instead of 9-(naphthalen
[0291] MS: [M+H]+=625
SYNTHESIS EXAMPLE 10. Synthesis of BH-10
##STR00205##
[0293] <10-a> Preparation of Compound BH-10-a
[0294] Compound BH-10-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromonaphtho[2,1-b]benzofuran was used instead of Compound
BH-1-b, and (3-chlorophenyl)boronic acid was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0295] MS: [M+H]+=329
[0296] <10-b> Preparation of Compound BH-10-b
[0297] Compound BH-10-b was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 4-b except
that Compound BH-10-a was used instead of Compound BH-4-a.
[0298] MS: [M+H]+=421
[0299] <10-c> Preparation of Compound BH-10-c
[0300] Compound BH-10-c was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that Compound BH-10-b was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid, and
9-bromo-10-(naphthalen-1-yl)anthracene was used instead of Compound
BH-1-b.
[0301] MS: [M+H]+=597
[0302] <10-d> Preparation of Compound BH-10
[0303] Compound BH-10 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-10-c was used instead of 9-(naphthalen-1-yl)
anthracene.
[0304] MS: [M+H]+=625
SYNTHESIS EXAMPLE 11. Synthesis of BH-11
##STR00206##
[0306] <11-a> Preparation of Compound BH-11-a
[0307] Compound BH-11-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromonaphtho[2,1-b]benzofuran was used instead of Compound
BH-1-b, and (3-chloronaphthalen-2-yl)boronic acid was used instead
of naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0308] MS: [M+H]+=379
[0309] <11-b> Preparation of Compound BH-11-b
[0310] Compound BH-11-b was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 4-b except
that Compound BH-11-a was used instead of Compound BH-4-a.
[0311] MS: [M+H]+=471
[0312] <11-c> Preparation of Compound BH-11-c
[0313] Compound BH-11-c was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that Compound BH-11-b was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid, and
9-bromo-10-(naphthalen-1-yl)anthracene was used instead of Compound
BH-1-b.
[0314] MS: [M+H]+=647
[0315] <11-d> Preparation of Compound BH-11
[0316] Compound BH-11 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-11-c was used instead of 9-(naphthalen-1-yl)
anthracene.
[0317] MS: [M+H]+=677
SYNTHESIS EXAMPLE 12. Synthesis of BH-12
##STR00207##
[0319] <12-a> Preparation of Compound BH-12-a
[0320] Compound BH-12-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of
Compound BH-1-b, and naphtho[2,1-b]benzofuran-8-ylboronic acid was
used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0321] MS: [M+H]+=521
[0322] <12-b> Preparation of Compound BH-12
[0323] Compound BH-12 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-12-a was used instead of 9-(naphthalen-1-yl)
anthracene.
[0324] MS: [M+H]+=545
SYNTHESIS EXAMPLE 13. Synthesis of BH-13
##STR00208##
[0326] <13-a> Preparation of Compound BH-13-b
[0327] Compound BH-13-b was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 9-bromo-10-(naphthalen-2-yl)anthracene was used instead of
Compound BH-1-b, and naphtho[2,1-b]benzofuran-8-ylboronic acid was
used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0328] MS: [M+H]+=521
[0329] <13-b> Preparation of Compound BH-13
[0330] Compound BH-13 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-a except
that Compound BH-13-b was used instead of 9-(naphthalen-1-yl)
anthracene.
[0331] MS: [M+H]+=545
[0332] Synthesis Example 14. Synthesis of BH-14
##STR00209##
[0333] <14-a> Preparation of Compound BH-14-a
[0334] Compound BH-14-a was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that 8-bromonaphtho[2,1-b]benzofuran was used instead of Compound
BH-1-b, and (3-chlorophenyl)boronic acid was used instead of
naphtho[2,1-b]benzofuran-11-ylboronic acid.
[0335] MS: [M+H]+=329
[0336] <14-b> Preparation of Compound BH-14-b
[0337] Compound BH-14-b was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 4-b except
that Compound BH-14-a was used instead of Compound BH-4-a.
[0338] MS: [M+H]+=421
[0339] <14-c> Preparation of Compound BH-14
[0340] Compound BH-14 was obtained by conducting synthesis and
purification in the same manner as in Synthesis Example 1-c except
that Compound BH-14-b was used instead of naphtho[2,1-b]
benzofuran-11-ylboronic acid.
[0341] MS: [M+H]+=612
<EXPERIMENTAL EXAMPLE 1: Device Example>Example 1
[0342] A glass substrate on which indium tin oxide (ITO) was coated
as a thin film to a thickness of 1,400 .ANG. was placed in
detergent-dissolved distilled water and ultrasonic cleaned. Herein,
a product of Fischer Co. was used as the detergent, and as the
distilled water, distilled water filtered twice with a filter
manufactured by Millipore Co. was used. After the ITO was cleaned
for 30 minutes, ultrasonic cleaning was repeated twice using
distilled water for 10 minutes. After the cleaning with distilled
water was finished, the substrate was ultrasonic cleaned with
solvents of isopropyl alcohol, acetone and methanol, then dried,
and then transferred to a plasma cleaner. In addition, the
substrate was cleaned for 5 minutes using oxygen plasma, and then
transferred to a vacuum deposition apparatus.
[0343] On the transparent ITO electrode prepared as above, the
following HI-A and HATCN were thermal vacuum deposited to
thicknesses of 650 .ANG. and 50 .ANG., respectively, to form a
first hole injection layer and a second hole injection layer. On
the hole injection layer, a hole transfer layer was formed by
vacuum depositing the following HT-A to a thickness of 600 .ANG..
The following HT-B was vacuum deposited to a thickness of 50 .ANG.
on the hole transfer layer to form an electron blocking layer.
[0344] Subsequently, on the electron blocking layer, a light
emitting layer was formed to a thickness of 200 .ANG. by vacuum
depositing the following Compound BD-A as a blue light emitting
dopant in 4 wt% with respect to the total weight of the light
emitting layer, and the following BH-1 as a host in 96 wt% with
respect to the total weight of the light emitting layer.
[0345] Then, on the light emitting layer, the following Compound
ET-A was vacuum deposited to 50 A as a first electron transfer
layer, and subsequently, the following ET-B and LiQ were vacuum
deposited in a weight ratio of 1:1 to a thickness of 360 .ANG. to
form a second electron transfer layer. An electron injection layer
was formed on the second electron transfer layer by vacuum
depositing LiQ to a thickness of 5 A. On the electron injection
layer, a cathode was formed by depositing aluminum and silver in a
weight ratio of 10:1 to a thickness of 220 .ANG., and then
depositing aluminum thereon to a thickness of 1000 .ANG..
[0346] In the above-described process, the deposition rates of the
organic materials were maintained at 0.4 .ANG./sec to 0.9
.ANG./sec, the deposition rate of the aluminum of the cathode was
maintained at 2 .ANG./sec, and the degree of vacuum during the
deposition was maintained at 5.times.10.sup.-8 torr to
1.times.10.sup.-7 torr, and as a result, an organic light emitting
device was manufactured.
##STR00210## ##STR00211## ##STR00212##
[0347] EXAMPLES 2 to 14
[0348] Organic light emitting devices of Examples 2 to 14 were each
manufactured in the same manner as in Example 1 except that
compounds described in the following Table 1 were each used as the
host of the light emitting layer instead of Compound BH-1.
##STR00213## ##STR00214## ##STR00215## ##STR00216##
##STR00217##
COMPARATIVE EXAMPLES 1 and 2
[0349] Organic light emitting devices of Comparative Examples 1 and
2 were each manufactured in the same manner as in Example 1 except
that compounds described in the following Table 1 were each used as
the host of the light emitting layer instead of Compound BH-1.
##STR00218##
[0350] For each of the organic light emitting devices of
[0351] Examples 1 to 14 and Comparative Examples 1 and 2, voltage
and efficiency (cd/A/y) when applying current density of 10
mA/cm.sup.2 and a lifetime (LT95) when applying current density of
20 mA/cm.sup.2 were measured, and the results are shown in the
following Table 1. Herein, LT95 means time taken for luminance to
decrease to 95% when employing initial luminance at current density
of 20 mA/cm.sup.2 as 100%, and the percentage is shown based on
Comparative Example 1.
TABLE-US-00001 TABLE 1 10 mA/cm.sup.2 Light Driving Converted
Emitting Layer Voltage Efficiency 20 mA/cm.sup.2 Host (V) (cd/A/y)
LT95 (%) Example 1 BH-1 3.54 42.0 179 Example 2 BH-2 3.55 41.3 211
Example 3 BH-3 3.53 40.3 203 Example 4 BH-4 3.54 43.5 183 Example 5
BH-5 3.56 44.6 190 Example 6 BH-6 3.47 44.2 197 Example 7 BH-7 3.57
44.7 225 Example 8 BH-8 3.18 40.4 182 Example 9 BH-9 3.32 39.3 175
Example 10 BH-10 3.45 41.3 183 Example 11 BH-11 3.21 43.5 162
Example 12 BH-12 3.57 40.5 196 Example 13 BH-13 3.54 40.1 188
Example 14 BH-14 3.41 42.3 161 Comparative BH-A 3.72 38.3 100
Example 1 Comparative BH-B 3.68 36.0 109 Example 2
[0352] In Table 1, the compound of Chemical Formula 1 according to
one embodiment of the present specification has structural
properties of having excellent electron and hole transfer. In
addition, Chemical Formula 1 had improved molecular stability by
including deuterium as a substituent. Accordingly, Examples 1 to 14
including the compound in the light emitting layer of the organic
light emitting device had superior efficiency, driving voltage and
lifetime efficiency compared to the organic light emitting devices
of Comparative Examples 1 and 2 including a compound that does not
include deuterium.
* * * * *