KR20100131629A - Heteroarylamine derivatives and organoelectroluminescent device using the same - Google Patents

Abstract

PURPOSE: A heteroarylamine derivative and an organic electro luminescence containing the same are provided to lower driving voltage and to improve luminescence efficiency. CONSTITUTION: A heteroarylamine derivative is denoted by chemical formula 1. In chemical formula 1, Het1 is pyrrol group, pyrazole group, imidazole group, triazole group, oxazole group, pyridine group, dipyridyl group, terpyridyl group, pyrimidine group or triazine group. An organic electro luminescence device comprises an anode, cathode and a layer having an heteroarylamine derivative between the anode and cathode.

Description

Heteroarylamine derivatives and organoelectroluminescent device using the same

The present invention relates to an aromatic compound and an organic light emitting device using the same, and more particularly to a heteroarylamine derivative and an organic light emitting device having a low driving voltage and excellent luminous efficiency using the same.

The organic light emitting device is gradually expanding its application field to the display and lighting field of various electronic products, but the efficiency and lifespan characteristics are restricting the expansion of the application field. There is a lot of research going on. In terms of materials, the host-dopant system is mainly adopted as a method for maximizing luminous efficiency, and the dopant as a luminescent material is phosphorescent material, and CBP (4, 4'-N, N'-dicarbazolbipheny) and substances in which various substituents are introduced into carbazole (Japanese Patent Laid-Open No. 2008-0214244, Japanese Patent Laid-Open No. 2003-0133075) are known, but further improvement is required in terms of efficiency and lifetime characteristics.

The first object of the present invention is to provide a novel heteroarylamine derivative capable of manufacturing an organic electroluminescent device having a low driving voltage and high luminous efficiency.

In addition, a second problem to be solved by the present invention is to provide an organic electroluminescent device having improved properties by employing the heteroarylamine derivative.

In order to achieve the first object of the present invention provides a heteroarylamine derivative represented by the following formula (1).

 (Formula 1)

(In Chemical Formula 1,

m is an integer of 1 to 3, n is an integer of 0 to 3, wherein the sum of m and n is 3, when n or m is 2 or more, a plurality of Het ₁ , L and A are each independently the same Or different,

Het ₁ is a substituted or unsubstituted heteroaryl group having 2 to 5 carbon atoms containing 1 to 3 nitrogens or a substituted or unsubstituted condensed aromatic heterocycle having 8 to 40 carbon atoms,

L is a divalent linking group connecting N and A ₁ and is any one selected from a single bond, a phenylene group, a biphenylene group, and a naphthylene group,

A ₁ is substituted or unsubstituted condensed aromatic heterocyclic ring having 8 to 40 carbon atoms, substituted or unsubstituted styryl group, substituted or unsubstituted aryl group, substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, substituted or unsubstituted C 3 -40 cycloalkenyl group, substituted or unsubstituted aryl group having 6-40 carbon atoms, substituted or unsubstituted aralkyl group having 7-40 carbon atoms, substituted or unsubstituted heteroaryl group having 3-40 carbon atoms, substituted or unsubstituted C3 Selected from the group consisting of -40 heteroaralkyl groups)

According to one embodiment of the present invention, the substituents of Het ₁ and A ₁ are a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, an alkylsilyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 40 carbon atoms, and a carbon number 1-40 alkoxy group, C1-40 alkylamino group, C6-40 aryl group, C6-40 aryloxy group, C6-40 arylamino group, C6-40 arylsilyl group, carbon number It may be selected from the group consisting of 3-40 heteroaryl groups, the substituents of Het ₁ and A ₁ may be substituted monovalent, divalent or fused, or are bonded to each other substituted or unsubstituted saturated or unsaturated ring Can be formed.

In addition, according to another embodiment of the present invention, the substituents of Het ₁ and A ₁ may be substituted by other substituents, for example, hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, carbon number 1 -10 alkylsilyl groups, alkyl groups of 1-40 carbon atoms, alkoxy groups of 1-40 carbon atoms, alkylamino groups of 1-40 carbon atoms, aryl groups of 6-40 carbon atoms, aryloxy groups of 6-40 carbon atoms, 6- It may be substituted with one or more substituents selected from the group consisting of an arylamino group of 40, an arylsilyl group of 6-40 carbon atoms, a heteroaryl group of 3-40 carbon atoms.

According to another embodiment of the present invention, Het1 is a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, a pyridine group, a dipyridyl group, a terpyridine group, a pyridazine group, a pyrimidine group, It is preferably any one selected from the group consisting of triazine groups.

According to another embodiment of the present invention, the Het ₁ is an indole group, a carbazole group, a dibenzoazine group, an azaandrodol group, an indolocarbazole group, a benzofuran group, a dibenzofuran group, a thianaphthene group (thianaphthene) , Dibenzothiophene group, indazole group, benzimidazole group, imidazopyridine group, benzotriazole group, benzothiazole group, benzothiadiazole group, triazolopyrimidine group, purine group, quinoline group, benzoquinoline group, azo It is preferably any one selected from the group consisting of a cridine group, an isoquinoline group, a phenanthroline group, a phthalazine group, a quinazoline group, a phenoxaline group, a phenazine group, a phenanthroline group, and a phenoxazine group.

The heteroarylamine derivative according to the present invention may be, for example, any one compound selected from the group represented by the following formulas (5) to (75), but is not limited to these exemplary compounds.

(5) (6) (7) (8) (9)

(10) (11) (12) (13) (14)

(15) (16) (17) (18) (19)

(20) (21) (22) (23) (24)

(25) (26) (27) (28) (29)

(30) (31) (32) (33) (34)

(35) (36) (37) (38) (39)

(40) (41) (42) (43) (44)

(45) (46) (47) (48) (49)

(50) (51) (52) (53)

(54) (55) (56)

(57) (58) (59) (60)

(61) (62) (63)

(64) (65) (66)

(67) (68)

(69) (70) (71) (72) (73)

(74) (75)

The present invention, in order to achieve the second technical problem, an anode; Cathode; And it provides an organic electroluminescent device having a layer comprising a heteroarylamine derivative represented by the formula (1) interposed between the anode and the cathode.

According to an embodiment of the present invention, the anode and the cathode further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer The heteroarylamine derivative may be included in the light emitting layer between the anode and the cathode, and the thickness of the light emitting layer is preferably 50 to 2,000 Pa.

According to another embodiment of the present invention, the hole injection layer, the hole transport layer, the hole blocking layer, the light emitting layer, the electron blocking layer, the electron transport layer and the electron injection layer is preferably formed by a single molecule deposition method or a solution process.

In addition, according to another embodiment of the present invention, the organic light emitting display device is preferably used for a display device, a display device and a monochrome or white lighting device.

By using the heteroarylamine derivative according to the present invention, it is possible to provide an organic light emitting device having a low driving voltage and excellent luminous efficiency.

The present invention is a derivative having a basic skeleton of the heteroarylamine represented by the formula (1) can be effectively used in all layers of the organic field device, especially when employed as a light emitting layer host, hole and electron movement is easy, the balance between holes and electrons Since it is possible to maximize the exciton formation in the light emitting layer.

Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like. Halogen atom, hydroxy group, nitro group, cyano group, silyl group (in this case referred to as "alkylsilyl group"), substituted or unsubstituted amino group (-NH2, -NH (R), -N (R ') (R' '), R' and R "are independently of each other an alkyl group having 1 to 10 carbon atoms, in this case referred to as an" alkylamino group "), a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 20 carbon atoms, Halogenated alkyl group of 1 to 20 carbon atoms, alkenyl group of 1 to 20 carbon atoms, alkynyl group of 1 to 20 carbon atoms, heteroalkyl group of 1 to 20 carbon atoms, aryl group of 6 to 20 carbon atoms, aralkyl group of 6 to 20 carbon atoms, carbon number 6 to 20 heteroaryl group or 6 to 20 carbon atoms It may be substituted with an alkyl group Le.

Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like. At least one hydrogen atom of the alkoxy group may be substituted with the same substituent as in the alkyl group.

The aryl group used in the compound of the present invention means an aromatic system including one or more rings, and the rings may be attached or fused together by a pendant method. The aryl group also includes non-condensed aromatic groups. Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, chrysenyl, and fluoranthenyl, and examples of the non-condensed aromatic group include biphenyl group, terphenyl group, and the like. Corresponding. At least one hydrogen atom of the aryl group may be substituted with the same substituent as in the alkyl group (for example, "arylamino group" when substituted with an amino group, "arylsilyl group" when substituted with a silyl group, oxy When substituted with a group, referred to as an "aryloxy group".

The heteroaryl group which is a substituent used in the compound of the present invention means a ring aromatic system having 3 to 30 carbon atoms containing 1, 2 or 3 hetero atoms selected from N, O or S, and the remaining ring atoms are carbon. Can be attached together in a pendant manner. When the heteroaryl group is fused with an aryl group or another heteroaryl group, this is called a condensed aromatic heterocycle. Specific examples of the heteroaryl group include pyrrole group, furan group, thiophene group, bithiophene group, terthiophene group, pyrazole group, imidazole group, triazole group, isoxazole group, oxazole group, oxadiazole group, pyridine group, di Pyridyl groups, terpyridine groups, pyridazine groups, pyrimidine groups, pyrazine groups, triazine groups and the like.

Specific examples of the condensed aromatic heterocyclic group include indole group, carbazole group, dibenzoazepine group, azaanddol group, indolocarbazole group, benzofuran group, dibenzofuran group, thianaphthene group, dibenzothiophene group, Indazole group, benzimidazole group, imidazopyridine group, benzotriazole group, benzothiazole group, benzothiadiazole group, triazolopyrimidine group, purine group, quinoline group, benzoquinoline group, acridine group, isoquinoline group, Phenanthroline groups, phthalazine groups, quinazoline groups, phenoxaline groups, phenazine groups, phenanthroline groups, phenoxazine groups and the like.

At least one hydrogen atom of the heteroaryl group and the condensed aromatic heterocycle may be substituted with the same substituent as in the alkyl group.

In addition, the present invention, in order to achieve the second technical problem, an anode; Cathode; And it provides an organic electroluminescent device comprising a layer comprising a heteroarylamine derivative represented by the formula represented between the anode and the cathode.

Referring to the organic light emitting device according to the present invention in more detail, the organic light emitting device comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer between the anode and the cathode. The hole injection layer, the hole transport layer, the electron transport layer and the electron injection layer may further increase the probability of light emitting coupling in the light emitting layer by efficiently transferring holes or electrons to the light emitting layer.

The hole injection layer and the hole transport layer are laminated to facilitate the injection of holes from the anode and the transport of the injected holes. As the material for the hole transport layer, electron donor molecules having small ionization potential are used. Diamine, triamine or tetraamine derivatives based on amines are frequently used. In the present invention, as the material of the hole transport layer, as long as it is commonly used in the art, various materials can be used without limitation, for example, N, N'-bis (3-methylphenyl) -N, N '-Diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD ) Can be used. In addition, a hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc or Starburst type amines such as TCTA, m-MTDATA, IDE406 (manufactured by Idemitsu Corp.) and the like can be used.

CuPc TCTA

           m-MTDATA

An organic light emitting layer is stacked on the hole transport layer, and the organic light emitting layer may be made of a single material or may be made of a host / dopant.

In general, when the compound is used as a single material, a host / dopant-based light emitting layer is preferable, because an intermolecular interaction produces a mound peak at long wavelengths, resulting in poor color purity, and low efficiency due to a light emission decay effect. The heteroarylamine derivative may be used as a host material in the host / dopant light emitting layer. In the host / dopant light emitting layer, a host material generally uses CBP (4,4'-dicarbazolyl-1,1'-biphenyl), and a dopant material uses Ir (ppy) 3 a lot, but is generally used in the art. It is not particularly limited as long as it is used as. The electron transport layer serves to increase the chance of recombination in the light emitting layer by smoothly transporting electrons supplied from the cathode to the light emitting layer and suppressing movement of holes that are not bonded in the light emitting layer. Such electron transport layer material is not particularly limited as long as it is a material used in the art, for example, Alq 3 (tri-8-hydroxyquinoline aluminum), PBD (2- (4-biphenylyl) -5- ( 4-t-butylphenyl) -1,3,4-oxadiazole), TNF (2,4,7-trinitro fluorenone), BMD, BND and the like can be used.

Meanwhile, an electron injection layer (EIL), which facilitates electron injection from the cathode and ultimately improves power efficiency, may be further stacked on the electron transport layer. Also commonly used in the art may be used without particular limitation, for example, it may be used a material such as LiF, NaCl, CsF, Li2O, BaO.

Furthermore, in addition to the above-described hole injection layer, hole transport layer, electron transport layer, and electron injection layer, the organic light emitting device according to the present invention may further include additional functional laminated structures such as a hole blocking layer or an electron blocking layer. . At this time, the hole blocking layer serves to prevent such a problem by using a material having a very low HOMO level because the life and efficiency of the device is reduced when holes are introduced into the cathode through the organic light emitting layer. The material constituting the hole blocking layer is not particularly limited, but must have an ionization potential higher than that of the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

More specifically, FIGS. 1A to 1F illustrate organic light emitting diodes having various types of stacked structures. Referring to this, the organic light emitting diode of FIG. 1A includes an anode / hole injection layer / light emitting layer / cathode. The organic electroluminescent device of FIG. 1B has a structure consisting of an anode / hole injection layer / light emitting layer / electron injection layer / cathode. In addition, the organic light emitting display device of FIG. 1c has a structure of an anode / hole injection layer / hole transporting layer / light emitting layer / cathode, and the organic light emitting device shown in FIG. 1d includes an anode / hole injection layer / hole transporting layer / light emitting layer / electron injection. The organic electroluminescent device of FIG. 1E has a structure of a layer / cathode, and has an anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode. Finally, the organic electroluminescent device of FIG. 1F is an anode. It has a structure of / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode.

The organic electroluminescent device according to the present invention may include the heteroarylamine derivative in various laminated structures interposed between the anode and the cathode. Preferably, the heteroarylamine derivative is a host in the light emitting layer between the anode and the cathode. Can be used as a substance.

In addition, the thickness of the light emitting layer including the heteroarylamine derivative may be 50 to 2,000 kPa, but when the thickness is less than 50 kPa, the luminous efficiency is lowered, and when it exceeds 2,000 kPa, the driving voltage is uneconomical. to be.

A method of manufacturing an organic light emitting display device according to the present invention will be described with reference to FIGS. 1A to 1F.

First, an anode material is coated on the substrate. As the substrate, a substrate used in a conventional light emitting device is used. A glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, as the anode material, materials commonly used in the art, such as transparent and highly conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), or zinc oxide (ZnO), may be used. . A hole injection layer is stacked on the anode, and then a hole transport layer is formed on the hole injection layer.

Next, after the light emitting layer is laminated on the hole transport layer, a hole blocking layer is selectively formed thereon. Finally, after the electron transport layer is laminated on the hole blocking layer, the electron injection layer may be selectively formed, and the organic light emitting diode according to the present invention may be manufactured by vacuum thermal depositing a metal for forming a cathode on the electron injection layer. Will be. Lamination of the organic layer is performed by one or more methods selected from the methods of vacuum thermal deposition, spin coating or inkjet printing.

On the other hand, as the metal for forming the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminium-lithium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), Magnesium-silver (Mg-Ag) or the like may be used, and a transmissive cathode using ITO or IZO may be used to obtain a front light emitting device.

Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples. However, the following synthesis examples and experimental examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Example 1 Preparation of a Compound of Formula 8

Compounds (Scheme 8) were synthesized by the following Schemes 1 to 5.

Scheme 1

2-bromocarbazole (30 g, 121.9 mmol), iodobenzene (38.3 g, 243.8 mmol), copper chloride (I) (0.24 g, 2.4 mmol), potassium carbonate (20.2 g, 146.3 mmol), dimethyl in a 500 ml reactor 240 mL of sulfoxide was added and refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, 200 mL of ethyl acetate was added, and filtered through Buchner. After extracting the filtrate with 500 mL of water, the organic layer was anhydrous and then dried under reduced pressure to remove the organic solvent. Hexane: ethyl acetate (10: 1) was used as a developing solvent for column separation. 19.8 g of white solid 2-bromo-N-phenylcarbazole were obtained. (50.4%)

Scheme 2

Dissolve 2-bromo-N-phenyl-carbazole (19.8 g, 0.061 mol) in 200 mL of tetrahydrofuran in a 500 mL round-bottom flask in nitrogen atmosphere, lower the temperature to -78 ° C, and 1.6M butyllithium (45.6 mL , 0.073 mol) was added slowly. After stirring for 2 hours, trimethyl borate (13.6 mL, 0.122 mol) was added thereto, and stirred at room temperature for 4 hours. After the reaction was completed, 80 mL of 2N hydrochloric acid was added, extracted with ethyl acetate and water. The organic layer was separated, anhydrous treated, the organic layer was concentrated, and hexane was added to give pale yellow crystals (N-phenylcarbazole-2-boronic acid). Was precipitated to give 12.6 g. (72%)

Scheme 3

3-bromopyridine (20 g, 126.6 mmol), aniline (15.3 g, 164.6 mmol), palladium acetate (0.6 g, 2.67 mmol), BINAP (1.6 g, 2.67 mmol), Na (t-OBu) ( 24.3 g, 5.34 mmol) and 200 mL of toluene were added and refluxed for 20 hours. After the reaction was completed, the mixture was cooled to room temperature, 600 mL of hexane was poured to precipitate crystals, and the precipitated solid was filtered, dissolved in 2 liters of methylene chloride, and extracted with 1 liter of water. The organic layer was anhydrous treated and then decompressed to remove the organic solvent. Ethyl acetate: hexane (2: 1) was used as a developing solvent for column separation to obtain 15 g of a light brown solid (N-3-pyridylaniline). (69.6%)

Scheme 4

In a 500 mL reactor, N-3-pyridylaniline (26.6 g, 156.3 mmol), 4-bromoiodobenzene (66 g, 234.4 mmol), copper chloride (I) (0.3 g, 3.1 mmol), potassium carbonate (32 g, 234.4 mmol) and 200 mL of dimethyl sulfoxide were added and refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, 200 mL of ethyl acetate was added, and filtered through a Buchner funnel. The filtrate was extracted three times with 500 ml of water, and then the organic layer was anhydrous and the organic solvent was removed under reduced pressure. Column separated using hexane: ethyl acetate (15: 1) as a developing solvent to give 23 g of a white solid (N-4-bromophenyl-N-3-pyridylaniline). (45.3%)

Scheme 5

N-4-bromophenyl-N-3-pyridylaniline (8.6 g, 0.026 mol) and N-phenylcarbazole-2-boronic acid (9.11 g, 0.031 mol), tetrakistriphenylphosphine palladium (0 ) (0.61 g, 0.52 mmol) and potassium carbonate (7.31 g, 0.053 mol) were all added to a 500 mL round bottom flask, and 69 mL of tetrahydrofuran, 69 mL of ethanol, and 26 mL of water were refluxed for 24 hours. After the reaction was completed, the organic layer was separated using ethyl acetate and water and subjected to anhydrous treatment to remove the solvent under reduced pressure. The obtained organic substance was column separated using ethyl acetate: hexane (1: 3) as a developing solvent, and 6.3 g of white solid (formula 8) was obtained. (49.7%)

Compounds represented by the formula (27, 61, 63, 68, 72) was synthesized in a similar manner to the formula (8). However, the method of known literature, Journal of Organic Chemistry, 2005, 70, 5014 was used for the synthesis of carbazole intermediates with various substituents. Also known methods for synthesis of indolocarbazole, Journal of Organic Chemistry, 1961. 26 (5) 1509-1511 and Journal of Chemical Society, 1963. 3097-3099.

Experimental Example

Fabrication of Organic Light Emitting Diode

The light emitting area of the ITO glass was patterned to have a size of 2 mm x mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1x10 ^-6 torr, and the organic material was placed on the ITO, DNTPD (700 kPa), NPD (300 kPa), compound + Ir (ppy) 3 (10%) prepared by the invention (300 Hz), Alq3 (350 Hz), LiF (5 Hz), and Al (1,000 Hz) were formed in this order and measured at 0.4 mA.

Comparative example

The organic light emitting diode device for the comparative example was manufactured in the same manner except that CBP was used instead of the compound prepared by the invention in the device structure of the above embodiment.

Host Dopant Doping concentration% ETL V A J
(mA / cm2) Cd / A CIEx CIEy CBP Ir (ppy) 3 10 Alq3 8.21 0.0004 10 38.81 0.29 0.62 8 Ir (ppy) 3 10 Alq3 7.00 0.0004 10 48.65 0.34 0.62 27 Ir (ppy) 3 10 Alq3 7.61 0.0004 10 48.68 0.31 0.62 61 lr (ppy) 3 10 Alq3 6.92 0.0004 10 53.72 0.30 0.63 63 lr (ppy) 3 10 Alq3 6.64 0.0004 10 50.41 0.31 0.62 68 lr (ppy) 3 10 Alq3 5.33 0.0004 10 50.56 0.34 0.62 72 lr (ppy) 3 10 Alq3 5.37 0.0004 10 49.58 0.35 0.62

As shown in the above table, the organic compound obtained by the present invention has a low driving voltage and excellent luminous efficiency as compared to CBP which is used as a phosphorescent material.

1A to 1F are cross-sectional views illustrating a laminated structure of organic light emitting diodes according to an exemplary embodiment of the present invention.

Claims (14)

Heteroarylamine derivatives represented by the following formula (1): (Formula 1)

(In Chemical Formula 1, m is an integer of 1 to 3, n is an integer of 0 to 3, wherein the sum of m and n is 3, when n or m is 2 or more, a plurality of Het ₁ , L and A are each independently the same Or different, Het ₁ is a substituted or unsubstituted heteroaryl group having 2 to 5 carbon atoms containing 1 to 3 nitrogens or a substituted or unsubstituted condensed aromatic heterocycle having 8 to 40 carbon atoms, L is a divalent linking group connecting N and A ₁ and is any one selected from a single bond, a phenylene group, a biphenylene group, and a naphthylene group, A ₁ is substituted or unsubstituted condensed aromatic heterocyclic ring having 8 to 40 carbon atoms, substituted or unsubstituted styryl group, substituted or unsubstituted aryl group, substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, substituted or unsubstituted C 3 -40 cycloalkenyl group, substituted or unsubstituted aryl group having 6-40 carbon atoms, substituted or unsubstituted aralkyl group having 7-40 carbon atoms, substituted or unsubstituted heteroaryl group having 3-40 carbon atoms, substituted or unsubstituted C3 Selected from the group consisting of -40 heteroaralkyl groups) The method of claim 1, The substituents of Het ₁ and A ₁ are hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, C1-10 alkylsilyl group, C1-40 alkyl group, C1-40 alkoxy group, C1 Group consisting of -40 alkylamino group, aryl group having 6-40 carbon atoms, aryloxy group having 6-40 carbon atoms, arylamino group having 6-40 carbon atoms, arylsilyl group having 6-40 carbon atoms, heteroaryl group having 3-40 carbon atoms Heteroarylamine derivatives, characterized in that at least one selected from. 3. The method of claim 2, Het ₁ and A ₁ substituent is a heteroarylamine derivative, characterized in that the monovalent, divalent or fused. The method of claim 3, wherein The substituents of Het ₁ and A ₁ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring heteroarylamine derivative. 3. The method of claim 2, The substituents of Het ₁ and A ₁ are hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, C1-10 alkylsilyl group, C1-40 alkyl group, C1-40 alkoxy group, C1 Group consisting of -40 alkylamino group, aryl group having 6-40 carbon atoms, aryloxy group having 6-40 carbon atoms, arylamino group having 6-40 carbon atoms, arylsilyl group having 6-40 carbon atoms, heteroaryl group having 3-40 carbon atoms Heteroarylamine derivatives, characterized in that further substituted with one or more substituents selected from. The method of claim 1, Het ₁ is any one selected from the group consisting of pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, pyridine group, dipyridyl group, terpyridine group, pyridazine group, pyrimidine group, triazine group Heteroarylamine derivatives. The method of claim 1, The Het ₁ is an indole group, a carbazole group, a dibenzoazine group, an azaandrodol group, an indolocarbazole group, a benzofuran group, a dibenzofuran group, a thianaphthene group, a dibenzothiophene group, an indazole group, a benz Imidazole group, imidazopyridine group, benzotriazole group, benzothiazole group, benzothiadiazole group, triazolopyrimidine group, purine group, quinoline group, benzoquinoline group, acridine group, isoquinoline group, phenanthroline group, Heteroarylamine derivatives, characterized in that any one selected from the group consisting of phthalazine group, quinazoline group, phenoxaline group, phenazine group, phenanthroline group, phenoxazine group. The method of claim 1, Heteroarylamine derivatives, characterized in that any one compound selected from compounds represented by formulas (5) to (75): (5) (6) (7) (8) (9)

(10) (11) (12) (13) (14)

(15) (16) (17) (18) (19)

(20) (21) (22) (23) (24)

(25) (26) (27) (28) (29)

(30) (31) (32) (33) (34)

(35) (36) (37) (38) (39)

(40) (41) (42) (43) (44)

(45) (46) (47) (48) (49)

(50) (51) (52) (53)

(54) (55) (56)

(57) (58) (59) (60)

(61) (62) (63)

(64) (65) (66)

(67) (68)

(69) (70) (71) (72) (73)

(74) (75)

Anode; Cathode; And a layer comprising a heteroarylamine derivative according to any one of claims 1 to 9 interposed between the anode and the cathode. 10. The method of claim 9, further comprising one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode. An organic light emitting display device. The organic electroluminescent device according to claim 10, wherein the heteroarylamine derivative is included in a light emitting layer between the anode and the cathode. The organic light emitting device of claim 11, wherein the light emitting layer has a thickness of 50 to 2,000 μm. The organic light emitting device of claim 12, wherein the hole injection layer, the hole transport layer, the hole blocking layer, the light emitting layer, the electron blocking layer, the electron transport layer, and the electron injection layer are formed by a single molecule deposition method or a solution process. . The organic light emitting device of claim 13, wherein the organic light emitting device is used in a display device, a display device, and a monochrome or white light emitting device.

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