KR20170052777A - Novel compound and organic electroluminescent device comprising same - Google Patents

Novel compound and organic electroluminescent device comprising same Download PDF

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KR20170052777A
KR20170052777A KR1020150154217A KR20150154217A KR20170052777A KR 20170052777 A KR20170052777 A KR 20170052777A KR 1020150154217 A KR1020150154217 A KR 1020150154217A KR 20150154217 A KR20150154217 A KR 20150154217A KR 20170052777 A KR20170052777 A KR 20170052777A
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group
halogen
substituted
unsubstituted
nitrile
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함호완
안현철
배유진
김동준
민병철
한정우
이형진
임동환
안자은
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주식회사 동진쎄미켐
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract

More particularly, the present invention relates to a novel compound, and more particularly, to a compound having at least two arylamine groups when applied to an organic light emitting device to form a HOMO that facilitates hole injection, thereby facilitating hole injection, Tg can be realized. In particular, since the molecular arrangement of the thin film is excellent, it is possible to increase the mobility, the low driving voltage, the low power consumption, the high efficiency and the long life.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound and an organic light emitting device comprising the compound.

The present invention relates to a novel compound and an organic light emitting device comprising the same.

In recent years, an organic light emitting device capable of being driven by a low voltage in a self-luminous mode has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, It has been attracting attention as a next generation display device because it is advantageous in terms of power consumption and has a wide color reproduction range.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending largely on functions. The light emitting material may be classified into a polymer and a low molecular weight depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excitation state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism, Can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color depending on the emission color. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant and the host.

Especially, amine derivatives having a carbazole skeleton have been extensively studied in the hole injecting and hole transporting materials used in such organic light emitting devices, but they have been difficult to put to practical use due to higher driving voltage, lower efficiency and shorter lifetime. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a material having excellent characteristics.

Korean Patent Publication No. 2014-0087805

In order to solve the above-mentioned problems, the present invention provides an organic electroluminescent device having excellent hole injection and hole transporting characteristics, high Tg, and excellent molecular arrangement of thin film, , Low power consumption, high efficiency, and long life.

The present invention also provides an organic electroluminescent device which is excellent in hole injection and hole transporting properties and can realize a high Tg and is particularly excellent in the molecular arrangement of the thin film, And an organic electroluminescent device.

In order to accomplish the above object, the present invention provides a compound represented by the following formula 1:

[Chemical Formula 1]

Figure pat00001

In this formula,

L 1 is a single bond, a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -30, C 1 -30 alkoxy group, an alkenyl group, C 6 unsubstituted or substituted by Silane C of 2 -30 of the An arylene group of -50 ; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl Rengi,

L 2 is a biphenyl group substituted or unsubstituted with a silane group, a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl group, a C 1 -30 alkoxy group, a C 2 -30 alkenyl group, Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of 1 -30 C, -30 C 1, C 2 -30 alkenyl group, an emitter which is unsubstituted or substituted with a phenyl group of the silane; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkenyl group, a fluorenyl which is unsubstituted or substituted with a silane of the C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 of the fluorene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl groups, aryl fused three ring heteroatoms which is unsubstituted or substituted by a silane group of ego,

Ar 1, Ar 2, Ar 3 and Ar 4 are each independently a heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 of the alkenyl group, A C 6 -50 aryl group unsubstituted or substituted with a silane group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl Lt; / RTI &

R 1 , R 2 , R 3 , R 4 , and R 5 are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; A silane group; Alkyl group of deuterium, halogen group, amino group, nitrile group, C 1 -30, which is unsubstituted or substituted with nitro; A C 2 -C 30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2 -C 30 alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C 1 - 30 which is unsubstituted or substituted with a nitro group; A C 6 -C 30 aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; An aryl group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 6 -50 which is unsubstituted or substituted by a group of the silane of; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl .

Also, the present invention provides an organic light emitting device including the compound represented by Formula 1.

The compound of the present invention can be easily injected into a hole by injecting a hole injecting compound containing at least two arylamine groups into an organic light emitting device, and can exhibit high Tg, In particular, since the molecular arrangement of the thin film is excellent, it is possible to increase the mobility, the low driving voltage, the low power consumption, the high efficiency and the long life.

1 schematically shows a cross section of an OLED according to an embodiment of the present invention.
The sign
10: substrate
11: anode
12: Hole injection layer
13: hole transport layer
14:
15: electron transport layer
16: cathode

The compounds of the present invention are represented by the following formula (1).

[Chemical Formula 1]

Figure pat00002

In this formula,

L 1 is a single bond, a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -30, C 1 -30 alkoxy group, an alkenyl group, C 6 unsubstituted or substituted by Silane C of 2 -30 of the An arylene group of -50 ; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl Rengi,

L 2 is a biphenyl group substituted or unsubstituted with a silane group, a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl group, a C 1 -30 alkoxy group, a C 2 -30 alkenyl group, Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of 1 -30 C, -30 C 1, C 2 -30 alkenyl group, an emitter which is unsubstituted or substituted with a phenyl group of the silane; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkenyl group, a fluorenyl which is unsubstituted or substituted with a silane of the C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 of the fluorene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl groups, aryl fused three ring heteroatoms which is unsubstituted or substituted by a silane group of ego,

Ar 1, Ar 2, Ar 3 and Ar 4 are each independently a heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 of the alkenyl group, A C 6 -50 aryl group unsubstituted or substituted with a silane group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl Lt; / RTI &

R 1 , R 2 , R 3 , R 4 , and R 5 are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; A silane group; Alkyl group of deuterium, halogen group, amino group, nitrile group, C 1 -30, which is unsubstituted or substituted with nitro; A C 2 -C 30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2 -C 30 alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C 1 - 30 which is unsubstituted or substituted with a nitro group; A C 6 -C 30 aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; An aryl group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 6 -50 which is unsubstituted or substituted by a group of the silane of; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl .

Specifically, the compound of Formula 1 is preferably a compound represented by Formula 2 or 3 below. In particular, since the molecular arrangement of the thin film is excellent, it is possible to increase the mobility, the low driving voltage, the low power consumption, the high efficiency and the long life.

(2)

Figure pat00003

(3)

Figure pat00004

Wherein L 1 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined in Formula (1)

X is O, S, CR 6 R 7 or SiR 8 R 9 , wherein R 6 , R 7 , R 8 and R 9 are each independently the same as defined for R 1 to R 5 .

More specifically, the compound represented by Formula 2 or 3 is preferably a compound represented by any one of the following formulas. In this case, the life and efficiency can be further improved.

[Formula 2-1]

Figure pat00005

[Formula 2-2]

Figure pat00006

[Formula 2-3]

Figure pat00007

[Formula 3-1]

Figure pat00008

[Formula 3-2]

Figure pat00009

[Formula 3-3]

Figure pat00010

In the above formulas, L 1 , Ar 1 , Ar 3 , Ar 4 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined in Formula (1)

Ar 5 and Ar 6 are each independently Ar 1 To Ar < 4 >.

In the present invention, specific examples of the compound represented by the formula (1) are as follows:

Figure pat00011
,
Figure pat00012
,
Figure pat00013
,
Figure pat00014
,
Figure pat00015
,
Figure pat00016
,
Figure pat00017
,
Figure pat00018
,
Figure pat00019
,
Figure pat00020
,
Figure pat00021
,
Figure pat00022
,
Figure pat00023
,
Figure pat00024
,
Figure pat00025
,
Figure pat00026
,
Figure pat00027
,
Figure pat00028
,
Figure pat00029
,
Figure pat00030
,
Figure pat00031
,
Figure pat00032
,
Figure pat00033
,
Figure pat00034
,
Figure pat00035
,
Figure pat00036
,
Figure pat00037
, ,
Figure pat00039
,
Figure pat00040
,
Figure pat00041
,
Figure pat00042
,
Figure pat00043
,
Figure pat00044
,
Figure pat00045
,
Figure pat00046
,
Figure pat00047
,
Figure pat00048
,
Figure pat00049
,
Figure pat00050
,
Figure pat00051
,
Figure pat00052
,
Figure pat00053
,
Figure pat00054
,
Figure pat00055
,
Figure pat00056
,
Figure pat00057
,
Figure pat00058
,
Figure pat00059
,
Figure pat00060
,
Figure pat00061
,
Figure pat00062
,
Figure pat00063
,
Figure pat00064
,
Figure pat00065
,
Figure pat00066
,
Figure pat00067
,
Figure pat00068
,
Figure pat00069
,
Figure pat00070
,
Figure pat00071
,
Figure pat00072
,
Figure pat00073
,
Figure pat00074
,
Figure pat00075
,
Figure pat00076
,
Figure pat00077
,
Figure pat00078
,
Figure pat00079
,
Figure pat00080
,
Figure pat00081
,
Figure pat00082
,
Figure pat00083
,
Figure pat00084
,
Figure pat00085
,
Figure pat00086
,
Figure pat00087
,
Figure pat00088
,
Figure pat00089
,
Figure pat00090
,
Figure pat00091

The compound of formula (1) according to the present invention is excellent in hole injection and hole transporting characteristics when applied to an organic light emitting device, has excellent electron blocking properties, can realize high triplet energy and high Tg, Power, high efficiency, and long life. In particular, when L 2 in the formula (1) includes a biphenyl group or a fluorene group, the molecular arrangement of the thin film is excellent, so that the mobility can be increased, the driving voltage can be reduced, the power consumption can be reduced, and high efficiency and long life can be obtained.

The compounds of the present invention may also be prepared via the following Reaction Scheme 1 or 2:

[Reaction Scheme 1]

Figure pat00092

[Reaction Scheme 2]

Figure pat00093

Wherein L 1 , L 2 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined in Chemical Formula (1).

Also, the present invention provides an organic light emitting device comprising a compound represented by Formula 1 in an organic material layer. Specifically, it is included as a hole injecting material or a hole transporting material, At this time, the compound of the present invention may be used alone or in combination with a known organic light emitting compound.

In addition, the organic light emitting device of the present invention includes one or more organic layers including the compound represented by Formula 1, and the method of manufacturing the organic light emitting device will now be described.

The organic light emitting device includes an organic layer such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode One or more can be included.

First, an anode electrode material having a high work function is deposited on the substrate to form an anode. At this time, the substrate can be a substrate used in a conventional organic light emitting device, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. The anode electrode material can be deposited by a conventional anode formation method, and specifically, it can be deposited by a deposition method or a sputtering method.

Then, a hole injecting layer may be formed on the anode electrode. Specifically, the hole injecting layer may be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, or a Langmuir-Blodgett (LB) method. More specifically, when the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal characteristics of the desired hole injection layer, and the like. A deposition temperature, a degree of vacuum of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 Å / sec, and a layer thickness range of 10 Å to 5 μm.

The hole injection layer material may be a compound represented by the formula (1) of the present invention, or may be used together with a known material. The known material is not particularly limited, and a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a star burst type amine derivative TCTA (4,4 ', 4 "-tri (N-carbazolyl) M-MTDAPA (4,4 ', 4 "-tris (3-methylphenylamino) phenoxybenzene) , HI-406 (N 1, N 1 '- ( biphenyl-4,4'-diyl) bis (N 1 - (naphthalen-1-yl) -N 4, N 4 - diphenyl-1,4-benzene Diamine) can be used as the hole injection layer material.

Next, a hole transport layer may be formed on the hole injection layer. Specifically, the hole transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. More specifically, in the case of forming the hole transporting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, the conditions can be selected in substantially the same range as the formation of the hole injection layer.

The hole transport layer material may be a compound represented by the general formula (1) of the present invention, or may be used in combination with a known material. The known material is not particularly limited and may be selected arbitrarily from common known materials used in the hole transport layer. Specifically, the hole transport layer material may be a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a carbazole derivative such as N, N'-bis (3-methylphenyl) -N, N'- Phenyl) -4,4'-diamine (TPD), and N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine Derivatives and the like can be used.

Thereafter, a light emitting layer may be formed on the hole transporting layer. Specifically, the light emitting layer material can be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, a LB method and the like. More specifically, in the case of forming a light emitting layer by the vacuum vapor deposition method, the deposition conditions depend on the compound used Generally, it can be selected in a substantially same condition range as the formation of the hole injection layer. The light emitting layer material may be a known compound as a host or a dopant.

In addition, in addition to the compound as an example as a light emitting layer material is a fluorescent dopant Idemitsu Co. (Idemitsu Co.), available IDE102 or IDE105, or BD142 (N 6, N 12 in-bis (3,4-dimethylphenyl) -N 6, N 12 -dimethyisilclycene-6,12-diamine), phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium) as the phosphorescent dopant, F2Irpic (III) bis [4,6-difluorophenyl) -pyridinate-N, C2 '] picolinate) and UDC's red phosphorescent dopant RD61 can be vacuum vacuum deposited (doped).

When the phosphorescent dopant is used together with the phosphorescent dopant, a hole blocking material (HBL) may be further deposited by vacuum evaporation or spin coating to prevent triplet excitons or holes from diffusing into the electron transport layer. The hole blocking material that can be used at this time is not particularly limited, but any known hole blocking material may be used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open Publication No. 11-329734 (A1) can be exemplified. Typically, Balq (bis Phenanthrolines based compounds such as UDC company BCP (bassocouroin), and the like can be used.

The electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like. Specifically, the electron transporting layer may be formed by a vacuum deposition method.

The electron transport layer material serves to stably transport electrons injected from the electron injection electrode. The material is not particularly limited, and examples thereof include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3 ), Or ET4 (6,6 '- (3,4-dimemethyl-1,1-dimethyl-1H-silanol-2,5-diyl) di-2,2'-bipyridine). In addition, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transport layer. Examples of the electron injection layer material include LiF, NaCl, CsF, Li 2 O, BaO Can be used.

The deposition condition of the electron transport layer varies depending on the compound used, but can be generally selected within the same range of conditions as the formation of the hole injection layer.

Then, an electron injecting layer may be formed on the electron transporting layer, and the electron transporting layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like, Can be formed by a vapor deposition method. Finally, a metal for forming a cathode is formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like, and used as a cathode. As the metal for cathode formation, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof can be used. Specific examples thereof include Li, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic light emitting device of the present invention can have an organic light emitting device having various structures as well as an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode structure, Layer or an intermediate layer of two layers may be further formed.

The organic light emitting device of the present invention includes a compound having at least two arylamine groups represented by Formula 1 to form HOMO that facilitates hole injection, thereby facilitating hole injection, excellent hole transporting property, and high Tg In particular, the molecular arrangement of the thin film is excellent, resulting in increased mobility, low driving voltage, low power consumption, high efficiency and long life.

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.

Synthesis of OP

Figure pat00094

Preparation of various OPs for the synthesis of the target compound was synthesized through the above steps.

The synthesis method of the following OP1 is as follows.

Figure pat00095

To a round bottom flask was added 4-bromo-N, N- diphenylaniline 25.0 g, N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine 26.0 g, t-BuONa 11.1 g, Pd 2 ( dba) 3 and 3.1 ml of (t-Bu) 3 P were dissolved in 500 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 25.5 g (yield: 57%) of intermediate OP1.

Synthesis method of OP2

Figure pat00096

OP2 was synthesized by following the procedure for the synthesis of OP1 except that N- (4-bromophenyl) -N-phenylnaphthalen-1-amine was used instead of 4-bromo-N and N-diphenylaniline in the synthesis of OP1 . (Yield: 56%)

Synthesis method of OP3

Figure pat00097

N4, N4'-di (naphthalen-1-yl) - [1,1 '-biphenyl] -4,4'-diamine was substituted for N4, N4'- -biphenyl] -4,4'-diamine was used to synthesize OP3 (yield: 53%).

Synthesis method of OP4

Figure pat00098

OP4 was synthesized by following the procedure for the synthesis of OP1 except that 3-bromo-9-phenyl-9H-carbazole was used instead of 4-bromo-N and N-diphenylaniline in the synthesis of OP1. %)

Synthesis method of OP5

Figure pat00099

OP5 was synthesized by following the procedure for the synthesis of OP1 except that 3-bromo-1-phenyl-1H-indole was used instead of 4-bromo-N, N-diphenylaniline in the synthesis of OP1. %)

Synthesis method of OP6

Figure pat00100

OP6 was synthesized by following the procedure for the synthesis of OP1 except that 3- (4-bromophenyl) -1-phenyl-1H-indole was used instead of 4-bromo-N and N-diphenylaniline in the synthesis of OP1 . (Yield: 55%).

Compound 1  synthesis

Figure pat00101

0.2 g of Pd 2 (dba) 3 and 0.2 ml of (t-Bu) 3 P were added to a round bottom flask with toluene 50 ml, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 2.51 g (yield 63%) of Compound 1.

m / z: 770.34 (100.0%), 771.34 (62.0%), 772.35 (18.3%), 773.35

Compound 2  synthesis

Figure pat00102

Compound 2 was synthesized by using OP4 instead of OP1 in the same manner as Compound 1. [ (Yield: 59%)

m / z: 768.33 (100.0%), 769.33 (61.0%), 770.33 (19.2%), 771.34 (3.6%), 769.32

Compound 3  synthesis

Figure pat00103

Preparation of 2- (4-bromophenyl) -1-phenyl-1H-indole

30.0 g of 2-bromo-1-phenyl-1H-indole, 36.4 g of bis (pinacolato) diboron, 0.4 g of Pd (dppf) Cl 2 and 32.5 g of KOAc were dissolved in 650 ml of toluene and then stirred under reflux in a round bottom flask. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then purified by column to obtain 28.85 g (yield) of intermediate 1-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- Yield: 82%). 19.35 g of the 1-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H- indole, 15 g of 1-bromo- dioxane (150 ml), K 2 CO 3 (2M) ml and Pd (PPh 3 ) 4 ( 1.9 g) were added, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 13.6 g (yield 71%) of 2- (4-bromophenyl) -1-phenyl-1H-indole.

Prepared in a round bottom flask 2.5 g OP1, the 2- (4-bromophenyl) -1- phenyl-1H-indole 1.65 g, t-BuONa 0.6 g, Pd 2 (dba) 3 0.16 g, (t-Bu) 3 P Was dissolved in 45 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure and then subjected to column purification to obtain 2.16 g (yield 59%) of Compound 3.

m / z: 846.37 (100.0%), 847.38 (67.6%), 848.38 (22.5%), 849.38 (5.1%), 847.37

Compound 4  synthesis

Figure pat00104

Compound 4 was synthesized by using OP2 instead of OP1 in the same manner as Compound 3. [ (Yield: 57%)

m / z: 896.39 (100.0%), 897.39 (71.9%), 898.39 (26.2%), 899.40 (5.9%), 897.38

Compound 5  synthesis

Figure pat00105

Compound 5 was synthesized by using OP3 in place of OPl in the same manner as Compound 3. [ (Yield: 57%)

m / z: 946.40 (100.0%), 947.41 (76.3%), 948.41 (28.7%), 949.41 (7.3%), 947.40 (1.5%), 950.42

Compound 6  synthesis

Figure pat00106

Compound 6 was synthesized by using OP4 instead of OP1 in the same manner as Compound 3. [ (Yield 60%)

m / z: 844.36 (100.0%), 845.36 (67.6%), 846.36 (23.1%), 847.37 (4.9%), 845.35

Compound 7  synthesis

Figure pat00107

Compound 7 was synthesized by using OP5 in place of OPl in the same manner as in Compound 3. [ (Yield: 55%)

m / z: 794.34 (100.0%), 795.34 (64.2%), 796.35 (19.6%), 797.35

Compound 8  synthesis

Figure pat00108

Compound 8 was synthesized by using OP6 in place of OPl in the same manner as Compound 3. [ (Yield: 61%)

m / z: 870.37 (100.0%), 871.38 (69.7%), 872.38 (24.0%), 873.38 (5.6%), 871.37 (1.5%), 872.37

Compound 9  synthesis

Figure pat00109

0.2 g of Pd 2 (dba) 3 and 0.2 ml of (t-Bu) 3 P were added to a round bottom flask with a solution of 3.0 g of OP1, 1.6 g of 3-bromo-1-phenyl- ml, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 2.59 g (yield 65%) of Compound 9.

m / z: 770.34 (100.0%), 771.34 (62.0%), 772.35 (18.3%), 773.35

Compound 10  synthesis

Figure pat00110

Compound 10 was synthesized by using OP4 instead of OP1 in the same manner as in Compound 9. [ (Yield: 63%)

m / z: 768.33 (100.0%), 769.33 (61.0%), 770.33 (19.2%), 771.34 (3.6%), 769.32

Compound 11  synthesis

Figure pat00111

Compound 11 was synthesized by using OP6 instead of OP1 in the same manner as in Compound 9. [ (Yield 67%)

m / z: 794.34 (100.0%), 795.34 (64.2%), 796.35 (19.6%), 797.35

Compound 12  synthesis

Figure pat00112

Preparation of 3- (4-bromophenyl) -1-phenyl-1H-indole

1-phenyl-1H-indole was used instead of 2-bromo-1-phenyl-1H-indole in the same manner as in the production of 2- (4-bromophenyl) .

OP1 3.0 prepared in a round bottom flask g, the 3- (4-bromophenyl) -1- phenyl-1H-indole 1.98 g, t-BuONa 0.75 g, Pd 2 (dba) 3 0.2 g, (t-Bu) 3 P Was dissolved in 55 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 2.41 g (yield: 55%) of Compound 12.

m / z: 846.37 (100.0%), 847.38 (67.6%), 848.38 (22.5%), 849.38 (5.1%), 847.37

Compound 13  synthesis

Figure pat00113

Compound 13 was synthesized by using OP4 instead of OP1 in the same manner as compound 12. [ (Yield: 57%)

m / z: 844.36 (100.0%), 845.36 (67.6%), 846.36 (23.1%), 847.37 (4.9%), 845.35

Compound 14  synthesis

Figure pat00114

2.05 g of N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine, 4.55 g of 3- (4-bromophenyl) 0.9 g of Pd 2 (dba) 3, 0.2 g of Pd 2 (dba) 3 and 0.5 ml of (t-Bu) 3 P were dissolved in 80 ml of toluene, After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 3.11 g (yield: 60%) of Compound 14.

m / z: 870.37 (100.0%), 871.38 (69.7%), 872.38 (24.0%), 873.38 (5.6%), 871.37 (1.5%), 872.37

Compound 15  synthesis

Figure pat00115

9,9-dimethyl-N2, N7-diphenyl-9H-fluorene-2,7-diamine instead of N4, N4'- diphenyl- [1,1'- biphenyl] -4,4'- Was used to synthesize compound 15. (Yield: 55%)

m / z: 910.40 (100.0%), 911.41 (73.0%), 912.41 26.3%, 913.41 6.4%, 911.40 1.5%, 912.40 1.1%

Compound 16  synthesis

Figure pat00116

Compound 16 was synthesized by using 3- (4-bromophenyl) -1-phenyl-1H-indole-d5 instead of 3- (4-bromophenyl) -1- (Yield: 55%)

m / z: 851.40 (100.0%), 852.41 (67.5%), 853.41 (22.4%), 854.41 (5.1%), 852.40

Compound 17  synthesis

Figure pat00117

Compound 17 was synthesized in the same manner as in Compound 12 using 3- (4-bromophenyl) -1-phenyl-1H-indole-d5 instead of 3- (4-bromophenyl) Respectively. (Yield: 58%)

m / z: 849.39 (100.0%), 850.39 (69.0%), 851.39 (23.1%), 852.40 (4.9%

Manufacture of organic light emitting device

An organic light emitting device was prepared according to the structure shown in FIG. The organic light emitting device includes an anode (hole injecting electrode 11) / a hole injecting layer 12 / a hole transporting layer 13 / a light emitting layer 14 / an electron transporting layer 15 / a cathode (electron injecting electrode 16) Respectively.

The following materials were used for the hole injecting layer 12, the hole transporting layer 13, the light emitting layer 14, and the electron transporting layer 15 of the following examples and comparative examples.

Figure pat00118
Figure pat00119
Figure pat00120
Figure pat00121
Figure pat00122
Figure pat00123
Figure pat00124
Figure pat00125
Figure pat00126
Figure pat00127
Figure pat00128
Figure pat00129

Manufacture of organic light emitting device

Example  One

The glass substrate coated with thin film of indium tin oxide (ITO) 1500 Å in thickness was washed with distilled water ultrasonic waves. After the distilled water was cleaned, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator evaporator) to form a hole injection layer compound 1 600 Å and a hole transport layer NPB 250 Å. Next, the light emitting layer was doped with BH01: BD01 5% to form a 300 Å layer. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transport layer, LiF 10 Å and aluminum (Al) 1000 Å were formed, and the device was encapsulated in a glove box to produce an organic light emitting device.

Example  2 to Example  17

An organic light emitting device was manufactured in the same manner as in Example 1, in which the hole injection layers were formed using the compounds 2 to 17, respectively.

Comparative Example  One

The device was fabricated in the same manner except that the hole injection layer of Example 1 was used as DNTPD instead of the compound 1.

Comparative Example  2 to Comparative Example  7

Except that the hole injection layer of Example 1 was used in Ref.1 to Ref.6 instead of Compound 1, respectively.

Evaluation of performance of organic light emitting device

A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). The performance of the organic light emitting devices of the examples and comparative examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under the atmospheric pressure condition, and the results are shown in Table 1.

Op. V mA / cm 2 Cd / A lm / w CIEx CIEy LT95
(hr) Example 1 4.15 10 6.49 5.22 0.141 0.113 28 Example 2 4.17 10 6.45 5.20 0.141 0.113 30 Example 3 4.07 10 6.45 5.45 0.142 0.112 32 Example 4 4.08 10 6.42 5.40 0.139 0.112 32 Example 5 4.08 10 6.43 5.35 0.138 0.110 31 Example 6 4.02 10 6.40 5.37 0.140 0.111 32 Example 7 4.03 10 6.40 5.50 0.140 0.110 33 Example 8 3.95 10 6.71 5.55 0.140 0.111 40 Example 9 3.99 10 6.67 5.45 0.140 0.110 35 Example 10 3.98 10 6.68 5.49 0.141 0.110 37 Example 11 3.99 10 6.68 5.55 0.142 0.111 37 Example 12 3.90 10 6.70 5.60 0.141 0.110 44 Example 13 3.91 10 6.95 5.62 0.139 0.109 47 Example 14 3.91 10 6.90 5.65 0.140 0.110 48 Example 15 3.90 10 6.89 5.60 0.140 0.111 50 Example 16 3.90 10 6.69 5.35 0.141 0.110 56 Example 17 3.91 10 6.95 5.91 0.140 0.110 57 Comparative Example 1 4.53 10 5.55 4.45 0.143 0.114 10 Comparative Example 2 6.12 10 1.58 1.01 0.164 0.210 - Comparative Example 3 5.81 10 4.28 3.25 0.147 0.125 - Comparative Example 4 5.40 10 5.04 3.52 0.147 0.131 - Comparative Example 5 5.42 10 5.13 3.64 0.147 0.120 5 Comparative Example 6 4.27 10 5.91 4.72 0.142 0.113 18 Comparative Example 7 4.35 10 6.02 4.90 0.143 0.112 22

In Table 1, " - " indicates that the light emission phenomenon disappears within one hour.

As shown in Table 1, the compounds of the present invention are superior to the compounds of Comparative Examples 1 to 7 in all respects. Compared with the comparative examples 2 to 5, the compound of the present invention has a high HOMO which is easily injected by hole substitution with two or more arylamine groups, and thus the driving voltage is remarkably lowered. Compared with Comparative Examples 1, 6 and 7, when biphenyl and fluorene groups were used instead of the phenylamine group between indole 2,3 and arylamine substitution, the hole mobility was excellent and the thin film arrangement was excellent and the efficiency and lifetime were significantly It can be seen that it is improved.

Claims (7)

A compound represented by the following formula (1):
[Chemical Formula 1]
Figure pat00130

In this formula,
L 1 is a single bond, a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C 1 -30, C 1 -30 alkoxy group, an alkenyl group, C 6 unsubstituted or substituted by Silane C of 2 -30 of the An arylene group of -50 ; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl Rengi,
L 2 is a biphenyl group substituted or unsubstituted with a silane group, a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl group, a C 1 -30 alkoxy group, a C 2 -30 alkenyl group, Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group of 1 -30 C, -30 C 1, C 2 -30 alkenyl group, an emitter which is unsubstituted or substituted with a phenyl group of the silane; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkenyl group, a fluorenyl which is unsubstituted or substituted with a silane of the C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 of the fluorene group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl groups, aryl fused three ring heteroatoms which is unsubstituted or substituted by a silane group of ego,
Ar 1, Ar 2, Ar 3 and Ar 4 are each independently a heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 of the alkenyl group, A C 6 -50 aryl group unsubstituted or substituted with a silane group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl Lt; / RTI &
R 1 , R 2 , R 3 , R 4 , and R 5 are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; A silane group; Alkyl group of deuterium, halogen group, amino group, nitrile group, C 1 -30, which is unsubstituted or substituted with nitro; A C 2 -C 30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C 2 -C 30 alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C 1 - 30 which is unsubstituted or substituted with a nitro group; A C 6 -C 30 aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; An aryl group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 6 -50 which is unsubstituted or substituted by a group of the silane of; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C 1 -30 alkyl, C 1 -30 alkoxy group, C 2 -30 alkenyl, C 2 -50 which is unsubstituted or substituted with a silane of the heteroaryl . The method according to claim 1,
Wherein said compound is represented by the following formula (2) or (3):
(2)
Figure pat00131

(3)
Figure pat00132

Wherein L 1 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined in Formula (1)
X is O, S, CR 6 R 7 or SiR 8 R 9 , wherein R 6 , R 7 , R 8 and R 9 are each independently the same as defined for R 1 to R 5 . The method according to claim 1,
Wherein said compound is represented by any one of the following formulas:
[Formula 2-1]
Figure pat00133

[Formula 2-2]
Figure pat00134

[Formula 2-3]
Figure pat00135

[Formula 3-1]
Figure pat00136

[Formula 3-2]
Figure pat00137

[Formula 3-3]
Figure pat00138


In the above formulas, L 1 , Ar 1 , Ar 3 , Ar 4 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined in Formula (1)
Ar 5 and Ar 6 are each independently Ar 1 To Ar < 4 >. 3. The method according to claim 1 or 2,
A compound represented by any one of the following formulas:
Figure pat00139
,
Figure pat00140
,
Figure pat00141
,
Figure pat00142
,
Figure pat00143
,
Figure pat00144
,
Figure pat00145
,
Figure pat00146
,
Figure pat00147
,
Figure pat00148
,
Figure pat00149
,
Figure pat00150
,
Figure pat00151
,
Figure pat00152
,
Figure pat00153
,
Figure pat00154
,
Figure pat00155
,
Figure pat00156
,
Figure pat00157
,
Figure pat00158
,
Figure pat00159
,
Figure pat00160
,
Figure pat00161
,
Figure pat00162
,
Figure pat00163
,
Figure pat00164
,
Figure pat00165
,
Figure pat00166
,
Figure pat00167
,
Figure pat00168
,
Figure pat00169
,
Figure pat00170
,
Figure pat00171
,
Figure pat00172
,
Figure pat00173
,
Figure pat00174
,
Figure pat00175
,
Figure pat00176
,
Figure pat00177
,
Figure pat00178
,
Figure pat00179
,
Figure pat00180
,
Figure pat00181
,
Figure pat00182
,
Figure pat00183
,
Figure pat00184
,
Figure pat00185
,
Figure pat00186
,
Figure pat00187
,
Figure pat00188
,
Figure pat00189
,
Figure pat00190
,
Figure pat00191
,
Figure pat00192
,
Figure pat00193
,
Figure pat00194
,
Figure pat00195
,
Figure pat00196
,
Figure pat00197
,
Figure pat00198
,
Figure pat00199
,
Figure pat00200
,
Figure pat00201
,
Figure pat00202
,
Figure pat00203
,
Figure pat00204
,
Figure pat00205
,
Figure pat00206
,
Figure pat00207
,
Figure pat00208
,
Figure pat00209
,
Figure pat00210
,
Figure pat00211
,
Figure pat00212
,
Figure pat00213
,
Figure pat00214
,
Figure pat00215
,
Figure pat00216
,
Figure pat00217
,
Figure pat00218
,
Figure pat00219
 An organic light-emitting device comprising at least one organic compound layer containing an anode, a cathode and a compound according to any one of claims 1 to 4 between two electrodes. 6. The method of claim 5,
Wherein the organic material layer comprises two or more compounds according to claim 4. 6. The method of claim 5,
Wherein the organic material layer contains the compound of claim 1 as a hole injecting material or a hole transporting material.








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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190078040A (en) * 2017-12-26 2019-07-04 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR20190088248A (en) * 2018-01-18 2019-07-26 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
WO2020262925A1 (en) * 2019-06-24 2020-12-30 덕산네오룩스 주식회사 Organic electric element

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190078040A (en) * 2017-12-26 2019-07-04 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR20190088248A (en) * 2018-01-18 2019-07-26 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
US11758806B2 (en) 2018-01-18 2023-09-12 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using the same, and an electronic device thereof
WO2020262925A1 (en) * 2019-06-24 2020-12-30 덕산네오룩스 주식회사 Organic electric element
KR20210000203A (en) * 2019-06-24 2021-01-04 덕산네오룩스 주식회사 Organic electric device
CN114008812A (en) * 2019-06-24 2022-02-01 德山新勒克斯有限公司 Organic electric element
US11812657B2 (en) 2019-06-24 2023-11-07 Duk San Neolux Co., Ltd. Organic electric element
CN117202755A (en) * 2019-06-24 2023-12-08 德山新勒克斯有限公司 Organic electronic component

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