KR20130105192A - Aromatic amine compound and organic electroluminescent device including the same - Google Patents

Abstract

PURPOSE: An aromatic amine compound is provided to show superior quantum efficiency compared with a compound for a conventional organic electroluminescent device and to lower driving voltage. CONSTITUTION: An aromatic amine compound for an organic electroluminescent device is denoted by structural formula 1. The organic electroluminescent device comprises a first electrode, a second electrode, and organic layers between the first and second electrodes. The organic layers contain the aromatic amine compound. The organic layers are a light emitting layer, a hole transport layer, or a hole injection layer.

Description

Aromatic amine compound and organic light emitting device including the same {AROMATIC AMINE COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME}

The present invention relates to an aromatic amine compound, and more particularly, to an aromatic amine compound that implements low-voltage driving and high efficiency light emitting characteristics when applied to an organic light emitting device, and an organic light emitting device including the same.

The organic light emitting device has a simpler structure, has various advantages in manufacturing process, and has high luminance and viewing angle compared to other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP), and a field emission display (FED). Due to its excellent characteristics, fast response speed and low driving voltage, development is being actively conducted to be used as a light source for a flat panel display such as a wall-mounted TV or a back light of a display, an illumination, a billboard.

In general, an organic light emitting diode recombines holes injected from an anode and electrons injected from a cathode when a DC voltage is applied to form an exciton, an electron-hole pair, and the excitons return to a stable ground state to emit corresponding energy. It is converted to light by transmitting it to the material.

In order to increase the efficiency and stability of organic light emitting devices, a low-voltage driving organic light emitting device is reported by forming a stacked organic thin film between two opposite electrodes by CW Tang of Eastman Kodak Corporation (CW Tang, SA Vanslyke, Applied Physics). Letters, Vol. 51, p. 913, 1987), studies on organic materials for multilayer thin film structured organic light emitting diodes have been actively conducted. The efficiency and lifespan of such stacked organic light emitting diodes is deeply related to the molecular structure of the material of the thin film. For example, the quantum efficiency is greatly influenced by the structure of the host material, the hole transporting layer material, or the electron transporting layer material among the materials constituting the thin film, and when the thermal stability is deteriorated, the crystallization of the material occurs at a high temperature or a driving temperature, Is shortened.

As a conventional aryl amine compound, various compounds are known, and have been used as hole layer materials or light emitting layer dopant materials in terms of hole transport characteristics and light emission characteristics. However, when used as a light emitting host material, the hole mobility is very large compared to the electron mobility, and an additional layered structure such as a hole blocking layer is required. The electron donor characteristic is strong, so that it is difficult to use as a light emitting layer host material.

Therefore, the first technical problem to be achieved by the present invention is to solve the problems of the prior art, the organic electroluminescence with a hole transport material, a hole injection material, a light emitting layer material, a host material of the light emitting layer, an electron transport material, and an electron injection material The present invention provides an aromatic amine compound having improved driving voltage and excellent quantum efficiency, power efficiency and current efficiency when applied to a device.

The second technical problem to be achieved by the present invention is to provide an organic electroluminescent device comprising an aromatic amine compound having a low driving voltage and high quantum efficiency, power efficiency and current efficiency.

 One embodiment of the present invention provides an aromatic amine compound for an organic light emitting device represented by the following structural formula 1.

[Structural formula 1]

 In the above formula 1,

Ring a is an aromatic ring having 5 to 7 nuclear atoms and having 1 to 3 nitrogen atoms in the nuclear atom,

,

,

,

,

, 치환 또는 비치환된 C_{1 -9}의 알킬기, 치환 또는 비치환된 C_{5 -30}의 알킬환기, 치환 또는 비치환된 C_{6 -30}의 아릴기, 또는 치환 또는 비치환된 C_{2 -30}의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -6}의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -3}의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_{6 -30}의 접합된 방향족 고리 또는 C_{2 -30}의 접합된 헤테로 방향족 고리를 형성할 수 있고, R ¹ to R ³ may be the same as or different from each other, R ¹ to R ³ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring Heteroaryl group, preferably hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted alkyl group of C _{1 -6,} more preferably a hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted C _{1 -3} alkyl group, or can be bonded to a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated hetero aromatic ring together. There is,

R ⁴ to R ⁸ may be the same or different from each other, R ⁴ to R ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring heteroaryl group, preferably a hydrogen atom or an alkyl group substituted or unsubstituted C _{1 -6} ring, more preferably A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or combine with a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated heteroaromatic ring Can,

Ar ¹ to Ar ⁴ may be the same or different from each other, Ar ¹ to Ar ⁴ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or hetero-substituted or unsubstituted C _{2 -30} Exchange aryl group, preferably a heteroaryl group, more preferably a hydrogen atom, a substituted or unsubstituted C ₆ a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted C _{2 -14} of the ring a heteroaryl group of _-10 aryl group or a substituted or unsubstituted C _{2 -10} of, still more preferably a hydrogen atom or a phenyl group,

Y ¹ is an oxygen atom or a sulfur atom, preferably an oxygen atom,

Ar ¹ to Ar ⁴ and R ¹ to R groups for "substituted" in ⁸ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of.

 Another embodiment of the present invention provides an aromatic amine compound for an organic light emitting device represented by the following Structural Formula 2.

[Structural formula 2]

In the above formula 2,

Ring b and ring c may be the same as or different from each other, ring b and ring c are each independently an aromatic ring having 5 to 7 nuclear atoms and 1 to 3 nitrogen atoms in the nuclear atom,

,

,

,

,

, 치환 또는 비치환된 C_{1 -9}의 알킬기, 치환 또는 비치환된 C_{5 -30}의 알킬환기, 치환 또는 비치환된 C_{6 -30}의 아릴기, 또는 치환 또는 비치환된 C_{2 -30}의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -6}의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -3}의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_{6 -30}의 접합된 방향족 고리 또는 C_{2 -30}의 접합된 헤테로 방향족 고리를 형성할 수 있고,R ⁹ to R ¹¹ may be the same as or different from each other, R ⁹ to R ¹¹ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring Heteroaryl group, preferably hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted alkyl group of C _{1 -6,} more preferably a hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted C _{1 -3} alkyl group, or can be bonded to a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated hetero aromatic ring together. There is,

R ¹² to R ¹⁶ may be the same or different from each other, R ¹² to R ¹⁶ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted heterocyclic ring of the C _{2 -30} aryl group, preferably a hydrogen atom or a substituted or unsubstituted alkyl group of unsubstituted C _1-6, more preferably A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or combine with a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated heteroaromatic ring Can,

Ar ⁵ to Ar ⁸ may be the same or different from each other, Ar ⁵ to Ar ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or hetero-substituted or unsubstituted C _{2 -30} aryl group, preferably a heteroaryl group, more preferably a hydrogen atom, a substituted or unsubstituted C ₆ a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted C _{2 -14} of the ring a heteroaryl group of _-10 aryl group or a substituted or unsubstituted C _{2 -10} of, still more preferably a hydrogen atom or a phenyl group,

Y ² is an oxygen atom or a sulfur atom, preferably an oxygen atom,

Ar ⁵ to Ar ⁸ and R ⁹ to R groups for "substituted" at ¹⁶ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of.

 Yet another aspect of the present invention provides an aromatic amine compound for an organic light emitting device represented by Structural Formula 3 below.

[Structural Formula 3]

In the above formula 3,

Ring d, ring e and ring f may be the same or different from each other, and ring d, ring e and ring f each independently have 5 to 7 nuclear atoms, and aromatic rings having 1 to 3 nitrogen atoms in the nuclear atoms ego,

,

,

,

,

, 치환 또는 비치환된 C_{1 -9}의 알킬기, 치환 또는 비치환된 C_{5 -30}의 알킬환기, 치환 또는 비치환된 C_{6 -30}의 아릴기, 또는 치환 또는 비치환된 C_{2 -30}의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -6}의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-3의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_{6 -30}의 접합된 방향족 고리 또는 C_{2 -30}의 접합된 헤테로 방향족 고리를 형성할 수 있고, R ¹⁷ to R ¹⁹ may be the same as or different from each other, R ¹⁷ to R ¹⁹ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring Heteroaryl group, preferably hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted alkyl group of C _{1 -6,} more preferably a hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted alkyl group or a C _1-3 ring, in combination with the carbon atom of the neighboring benzene rings together may form a conjugated heteroaromatic ring of C _{6 -30} bonded aromatic ring or C _{2 -30} of the There is,

R ²⁰ to R ²⁴ may be the same or different from each other, R ²⁰ to R ²⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted heterocyclic ring of the C _{2 -30} aryl group, preferably a hydrogen atom or a substituted or unsubstituted alkyl group of unsubstituted C _1-6, more preferably A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or combine with a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated heteroaromatic ring Can,

Ar ⁹ to Ar ¹² are each the same or may be different, each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group or a substituted heteroaryl or unsubstituted C _{2 -30} group, preferably a a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted heteroaryl group of C _{2 -14,} more preferably an aryl group, a hydrogen atom, a substituted or unsubstituted ring or C _{6 -10} a substituted or unsubstituted heteroaryl groups in the ring C _{2 -10,} still more preferably a hydrogen atom or a phenyl group,

Y ³ is an oxygen atom or a sulfur atom, preferably an oxygen atom,

Ar ⁹ to Ar ¹² and R ¹⁷ to group for the "substituted" in R ²⁴ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of.

Another aspect of the invention, the first electrode; A second electrode; And an organic material layer between the first electrode and the second electrode.

The organic material layer provides an organic light emitting device comprising the aromatic amine compound according to the present invention.

In the present invention, the organic material layer may be a light emitting layer.

In the present invention, the organic material layer may be a hole transport layer.

In the present invention, the organic material layer may be a hole injection layer.

In the present invention, the organic material layer may be an electron transport layer.

In the present invention, the organic material layer may be an electron injection layer.

Another aspect of the invention, the first electrode; A second electrode; And a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer includes a host and a dopant.

The host provides an organic light emitting device, characterized in that it comprises an aromatic amine compound according to the present invention.

According to the present invention, the driving voltage is improved when applied to an organic light emitting device with a hole transport material, a hole injection material, a light emitting layer material, a host material of the light emitting layer, an electron transport material, and an electron injection material, and excellent quantum efficiency, power efficiency and current efficiency. The aromatic amine compound which shows can be provided.

In another aspect, the present invention provides an organic EL device comprising an aromatic amine compound having a low driving voltage and high quantum efficiency, power efficiency and current efficiency.

1 is a view schematically showing a cross section of an organic light emitting diode according to an embodiment of the present invention.
2 is a view schematically showing a cross section of an organic light emitting diode according to another exemplary embodiment of the present invention.
FIG. 3 is a graph showing an absorption spectrum, a solution (THF) emission spectrum, a solid emission spectrum, and a low temperature emission spectrum of Compound 2. FIG.

Hereinafter, a preferred embodiment of an aromatic amine compound for an organic light emitting device and an organic light emitting device including the same according to the present invention will be described in detail with reference to the chemical formula and the accompanying drawings, the same or corresponding configuration in referring to the accompanying drawings Elements are given the same reference numerals and redundant description thereof will be omitted.

However, the following description is not intended to limit the present invention to specific embodiments, and it is to be understood that the present invention includes all conversions, equivalents, and substitutes included in the spirit and technical scope of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

Furthermore, terms including an ordinal number such as first, second, etc. to be used below can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.

Also, when an element is referred to as being "formed" or "laminated" on another element, it may be directly attached or laminated to the front surface or one surface of the other element, It will be appreciated that other components may be present in the < / RTI >

Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms "comprise" or "have" are intended to indicate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, and one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, components, or a combination thereof.

As a technical means for achieving the above technical problem, an aspect of the present invention provides an aromatic amine compound for an organic light emitting device represented by the following structural formula (1).

[Structural formula 1]

In the above formula 1,

Ring a is an aromatic ring having 5 to 7 nuclear atoms and having 1 to 3 nitrogen atoms in the nuclear atom,

,

,

,

,

, 치환 또는 비치환된 C_1-9의 알킬기, 치환 또는 비치환된 C_{5 -30}의 알킬환기, 치환 또는 비치환된 C_{6 -30}의 아릴기, 또는 치환 또는 비치환된 C_{2 -30}의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -6}의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -3}의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_{6 -30}의 접합된 방향족 고리 또는 C_{2 -30}의 접합된 헤테로 방향족 고리를 형성할 수 있고, R ¹ to R ³ may be the same as or different from each other, R ¹ to R ³ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _1-9 alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the Heteroaryl group, preferably hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted alkyl group of C _{1 -6,} more preferably a hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted C _{1 -3} alkyl group, or can be bonded to a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated hetero aromatic ring together. There is,

R ⁴ to R ⁸ may be the same or different from each other, R ⁴ to R ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring heteroaryl group, preferably a hydrogen atom or an alkyl group substituted or unsubstituted C _{1 -6} ring, more preferably A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or combine with a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated heteroaromatic ring Can,

Ar ¹ to Ar ⁴ may be the same or different from each other, Ar ¹ to Ar ⁴ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or hetero-substituted or unsubstituted C _{2 -30} Exchange aryl group, preferably a heteroaryl group, more preferably a hydrogen atom, a substituted or unsubstituted C ₆ a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted C _{2 -14} of the ring a heteroaryl group of _-10 aryl group or a substituted or unsubstituted C _{2 -10} of, still more preferably a hydrogen atom or a phenyl group,

Y ¹ is an oxygen atom or a sulfur atom, preferably an oxygen atom,

Ar ¹ to Ar ⁴ and R ¹ to R groups for "substituted" in ⁸ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of.

 Another embodiment of the present invention provides an aromatic amine compound for an organic light emitting device represented by the following Structural Formula 2.

[Structural formula 2]

In the above formula 2,

Ring b and ring c may be the same as or different from each other, ring b and ring c are each independently an aromatic ring having 5 to 7 nuclear atoms and 1 to 3 nitrogen atoms in the nuclear atom,

,

,

,

,

, 치환 또는 비치환된 C_{1 -9}의 알킬기, 치환 또는 비치환된 C_{5 -30}의 알킬환기, 치환 또는 비치환된 C_{6 -30}의 아릴기, 또는 치환 또는 비치환된 C_{2 -30}의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -6}의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -3}의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_{6 -30}의 접합된 방향족 고리 또는 C_{2 -30}의 접합된 헤테로 방향족 고리를 형성할 수 있고,R ⁹ to R ¹¹ may be the same as or different from each other, R ⁹ to R ¹¹ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring Heteroaryl group, preferably hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted alkyl group of C _{1 -6,} more preferably a hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted C _{1 -3} alkyl group, or can be bonded to a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated hetero aromatic ring together. There is,

R ¹² to R ¹⁶ may be the same or different from each other, R ¹² to R ¹⁶ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted heterocyclic ring of the C _{2 -30} aryl group, preferably a hydrogen atom or a substituted or unsubstituted alkyl group of unsubstituted C _1-6, more preferably A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or combine with a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated heteroaromatic ring Can,

Ar ⁵ to Ar ⁸ may be the same or different from each other, Ar ⁵ to Ar ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or hetero-substituted or unsubstituted C _{2 -30} aryl group, preferably a heteroaryl group, more preferably a hydrogen atom, a substituted or unsubstituted C ₆ a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted C _{2 -14} of the ring a heteroaryl group of _-10 aryl group or a substituted or unsubstituted C _{2 -10} of, still more preferably a hydrogen atom or a phenyl group,

Y ² is an oxygen atom or a sulfur atom, preferably an oxygen atom,

Ar ⁵ to Ar ⁸ and R ⁹ to R groups for "substituted" at ¹⁶ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of.

 Yet another aspect of the present invention provides an aromatic amine compound for an organic light emitting device represented by Structural Formula 3 below.

[Structural Formula 3]

In the above formula 3,

Ring d, ring e and ring f may be the same or different from each other, and ring d, ring e and ring f each independently have 5 to 7 nuclear atoms, and aromatic rings having 1 to 3 nitrogen atoms in the nuclear atoms ego,

,

,

,

,

, 치환 또는 비치환된 C_{1 -9}의 알킬기, 치환 또는 비치환된 C_{5 -30}의 알킬환기, 치환 또는 비치환된 C_{6 -30}의 아릴기, 또는 치환 또는 비치환된 C_{2 -30}의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_{1 -6}의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-3의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_{6 -30}의 접합된 방향족 고리 또는 C_{2 -30}의 접합된 헤테로 방향족 고리를 형성할 수 있고, R ¹⁷ to R ¹⁹ may be the same as or different from each other, R ¹⁷ to R ¹⁹ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring Heteroaryl group, preferably hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted alkyl group of C _{1 -6,} more preferably a hydrogen atom,

,

,

,

,

Or a substituted or unsubstituted alkyl group or a C _1-3 ring, in combination with the carbon atom of the neighboring benzene rings together may form a conjugated heteroaromatic ring of C _{6 -30} bonded aromatic ring or C _{2 -30} of the There is,

R ²⁰ to R ²⁴ may be the same or different from each other, R ²⁰ to R ²⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted heterocyclic ring of the C _{2 -30} aryl group, preferably a hydrogen atom or a substituted or unsubstituted alkyl group of unsubstituted C _1-6, more preferably A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or combine with a carbon atom of a neighboring benzene ring to form a C _{6 -30} conjugated aromatic ring or a C _{2 -30} conjugated heteroaromatic ring Can,

Ar ⁹ to Ar ¹² are each the same or may be different, each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group or a substituted heteroaryl or unsubstituted C _{2 -30} group, preferably a a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted heteroaryl group of C _{2 -14,} more preferably an aryl group, a hydrogen atom, a substituted or unsubstituted ring or C _{6 -10} a substituted or unsubstituted heteroaryl groups in the ring C _{2 -10,} still more preferably a hydrogen atom or a phenyl group,

Y ³ is an oxygen atom or a sulfur atom, preferably an oxygen atom,

Ar ⁹ to Ar ¹² and R ¹⁷ to group for the "substituted" in R ²⁴ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of.

R ¹ to R ²⁴ And Ar ¹ to Ar ¹² in the C _{6 -30} aryl group, as specific examples, a phenyl group, 1-naphthyl, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1- Phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group , 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terter Phenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p- tert-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4-methylbiphenylyl group or 4-tert-butyl-p-terphenyl-4-yl group etc. are mentioned.

Also R ¹ to R ²⁴ And Ar ¹ to Ar ¹² in the specific heteroaryl group of C _{2 -30} Examples of the 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl the group, pyrimidinyl group, a pyrido chewy, 2-pyridine group, 3 -Pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindoleyl group , 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3- Furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzo Furanyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuran Diary, 6-dibenzofuranyl group, 7-dibenzo Lanyl group, 8-dibenzofuranyl group, 9-dibenzofuranyl group, 2-benzothiophene, 3-benzothiophene, 4-benzothiophene, 5-benzothiophene, 6-benzothiophene, 7-benzo Ciophene, 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 6-dibenzothiophene, 7-dibenzothiophene, 8-dibenzosai Offen, 9-dibenzothiophene, 2-benzophosphole, 3-benzophosphole, 4-benzophosphole, 5-benzophosphole, 6-benzophosphole, 7-benzophosphole, 1-dibenzoforce Pole, 2-Dibenzophosphole, 3-Dibenzophosphole, 4-Ibenzophosphole, 6-Ibenzophosphole, 7-Dibenzophosphole, 8-Dibenzophosphole, 9-Ibenzophosphole, 2- Benzophosphole oxide, 3-benzophosphole oxide, 4-benzophosphole oxide, 5-benzophosphole oxide, 6-benzophosphole oxide, 7-benzophosphole oxide, 1-dibenzophosphole oxide, 2- Dibenzophosphoxide, 3-di Crude phosphol oxide, 4-dibenzophosphole oxide, 6-dibenzophosphole oxide, 7-dibenzophosphole oxide, 8-dibenzophosphole oxide, 9-dibenzophospholeoxide, quinolyl group, 3- Quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4- Isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group , 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1 , 7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenan Roline-5-Diary, 1,7-phenanthroline-6-diary, 1,7-phenanthroline-8-diary, 1,7-phenanthroline-9-diary, 1,7-phenanthroline- 10-diary, 1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthroline-5- Diary, 1,8-phenanthroline-6-diary, 1,8-phenanthroline-7-diary, 1,8-phenanthroline-9-diary, 1,8-phenanthroline-10-diary, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1, 9-phenanthroline-6-diary, 1,9-phenanthroline-7-diary, 1,9-phenanthroline-8-diary, 1,9-phenanthroline-10-diary, 1,10- Phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-diary, 2,9-phenanthrole Lin-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-diary, 2,9-phenanthroline- 6-diary, 2,9-phenanthroline-7-diary, 2,9-phenanthroline-8-diary, 2,9-phenanthroline-10-diary, 2,8-phenant Rollin-1-yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-diary, 2,8-phenanthroline- 6-diary, 2,8-phenanthroline-7-diary, 2,8-phenanthroline-9-diary, 2,8-phenanthrolineyl group, 2,7-phenanthroline-1-yl group, 2 , 7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-diary, 2,7-phenanthroline-6-diary, 2,7 -Phenanthroline-8-diary, 2,7-phenanthroline-9-diary, 2,7-phenanthroline-10-diary, 1-phenazineyl group, 2-phenazinediary group, 1-phenothiazin Diary, 2-phenothiazin diary, 3-phenothiazin diary, 4-phenothiazin diary, 10-phenothiazin diary, 1-phenoxazine diary, 2-phenoxazine diary, 3-phenoxazine diary, 4- Phenoxazineyl group, 10-phenoxazineyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2- Thienyl group, 3-thienyl group, 2-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrole-1-yl group, 3-methylpyrrole-2-yl group, 3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group, 2-tert-butyl Pyrrole-4-yl group, 3- (2-phenylpropyl) pyrrole-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl 3-indolyl group, 2-tert-butyl-1-indolyl group, 4-tert-butyl-1-indolyl group, 2-tert-butyl-3-indolyl group, or 4-tert-butyl-3-indolyl group Can be mentioned.

In addition, the R ¹ to specific examples include methyl and ethyl for the alkyl group of R ²⁴ of C _{1 -9,} n- propyl, n- pentyl, n- butyl, n- hexyl, n- heptyl, n- octyl, iso A propyl group, sec-butyl group, isobutyl group, tert- butyl group, etc. are mentioned.

In addition, the R ¹ to R ²⁴ of C _{5 -30} Specific examples of the alkyl ventilation may be mentioned cyclohexyl, cyclo heptyl, cyclo-octyl group and the like.

Specific examples of the thio group of C _{1 -30} as a group corresponding to the "substituted", methylthio, ethylthio, propyl thio, butyl-thio, pentylthio, hexylthio, tri (isopropyl) thio, tri (isobutyl) Thio, tri ( tert -butyl) thio, tri (2-butyl) thio, phenylthio, naphthylthio, biphenylthio, (3-methylphenyl) thio, (4-methylnaphthyl) thio, (2-methylbi Phenyl) thio group etc. are mentioned.

As a group corresponding to the "substituted" Specific examples of the group of C _{1 -30} silyl, trimethyl silyl, triethyl silyl, tributyl silyl, tri (isopropyl) silyl, tri (isobutyl) silyl, tri (tert - Butyl) silyl, tri (2-butyl) silyl, triphenylsilyl, trinaphthylsilyl, tribiphenylsilyl, tri (3-methylphenyl) silyl, tri (4-methylnaphthyl) silyl, tri (2-methylbi Phenyl) silyl, phenylmethylsilyl, phenylethylsilyl, naphthylmethylsilyl, naphthylethylsilyl, biphenylmethylsilyl, 3-methyl-phenylmethylsilyl, phenyl (isopropyl) silyl, naphthyl (isopropyl) silyl or A biphenyl (isopropyl) silyl group etc. are mentioned.

In order to improve the problems of the conventional aryl amine compounds, the present invention provides a driving voltage when applied to an organic light emitting device as a hole transport material, a hole injection material, a light emitting layer material, a host material of the light emitting layer, an electron transport material, and an electron injection material An aromatic amine compound was prepared, which improved and exhibited excellent quantum efficiency.

Hereinafter, although the chemical formula of 1-22 is illustrated in Table 1 as a chemical formula of the aromatic amine compound of this invention, this invention is not limited to the compound represented by these chemical formulas.

compound The compound The One

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

An organic EL device according to the present invention will be described with reference to the accompanying drawings. 1 is a view schematically showing the structure of an organic EL device of the present invention. The organic light emitting device including the aromatic amine compound represented by the above structural formulas 1 to 3 may be realized in various structures.

Referring to FIG. 1, one embodiment of the present invention may include a first electrode 110; A second electrode (150); And an organic material layer 130 formed between the first electrode 110 and the second electrode 150, wherein the organic material layer 130 includes the aromatic amine compound. An organic electroluminescent device is provided.

 According to another embodiment of the present invention, the organic material layer 130 may be a light emitting layer.

In addition, according to another embodiment of the present invention, the organic layer 130 may be a hole transport layer.

In addition, according to another embodiment of the present invention, the organic layer 130 may be a hole injection layer.

 In addition, according to another embodiment of the present invention, the organic layer 130 may be an electron transport layer.

In addition, according to another embodiment of the present invention, the organic layer 130 may be an electron injection layer.

Referring to Figure 2, another embodiment of the present invention, the first electrode 110; A second electrode (150); And a light emitting layer 135 between the first electrode 110 and the second electrode 150, wherein the light emitting layer 135 includes a host and a dopant. It can provide an organic light emitting device comprising an aromatic amine compound according to.

According to another embodiment of the present invention, a hole transport layer 133 may be further included between the first electrode 110 and the light emitting layer 135.

According to another embodiment of the present invention, a hole injection layer 131 may be further included between the first electrode 110 and the emission layer 135.

According to another embodiment of the present invention, an electron transport layer 137 may be further included between the second electrode 150 and the light emitting layer 135.

According to another embodiment of the present invention, an electron injection layer 139 may be further included between the second electrode 150 and the light emitting layer 135.

The organic electroluminescent device is preferably supported by a transparent substrate. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof include glass, transparent plastic film, and the like.

As the anode material of the organic EL device of the present invention, a metal, an alloy, an electrically conductive compound having a work function of 4 eV or more, or a mixture thereof can be used. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO ₂ and ZnO, which are metals, can be mentioned. The thickness of the positive electrode film is preferably 10 to 200 nm.

As a negative electrode material of the organic EL device of the present invention, a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV can be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy and aluminum alloy can be mentioned. In addition, aluminum / AlO ₂ , aluminum / lithium, magnesium / silver or magnesium / indium may be used. The thickness of the negative electrode film is preferably 10 to 200 nm. In order to increase the luminous efficiency of the organic EL device, at least one electrode preferably has a light transmittance of 10% or more. The sheet resistance of the electrode is preferably several hundred Ω / mm or less. The thickness of the electrode is 10 nm to 1 m, more preferably 10 to 400 nm. Such an electrode may be manufactured by forming the above electrode material into a thin film through vapor deposition or sputtering such as chemical vapor deposition (CVD), physical vapor deposition (PVD), or the like.

When the aromatic amine compound for an organic EL device of the present invention is used in at least one selected from the group consisting of a hole transport material, a hole injection material, a light emitting layer material, a host material of the light emitting layer, an electron transport material, and an electron injection material, Other hole transport materials, hole injection materials, hole injection materials, light emitting layer materials, host materials of the light emitting layer, electron transport materials, and electron injection material materials which are not used in the aromatic amine compound for the organic light emitting device of the present invention. At least one selected from the group consisting of a light emitting layer material, a host material of the light emitting layer, an electron transport material, and an electron injection material may be used.

Hereinafter, a hole transport material, a hole injection material, a light emitting layer material, a host material of the light emitting layer, an electron transport material, and an electron injection material will be described.

The hole transport layer or the hole injection layer of the present invention is a material commonly used as a hole transport material among photoconductive materials as a hole transport material and a hole injection material, and a known material used for the formation of a hole transport layer or a hole injection layer of an organic EL device. It may include. For example, N, N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS), N, N'-di (1-naphthyl) -N, N '-diphenylbenzidine (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'-diaminobiphenyl (TPD), N, N'-diphenyl-N, N'-Dinaphthyl-4,4'-diaminobiphenyl, N, N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N, N'N ' Porphyrin compound derivatives such as tetraphenyl-4,4'-diaminobiphenyl, copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin, aromatic tertiary in the main chain or side chain Polymer with amine, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (p-tolyl) amine, 4, 4 ', 4'-tris [N- Triarylamine derivatives such as (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives such as metal-free phthalocyanine, copper phthalocyanine, starburst Amine May be a conductor, enamine stilbene derivatives, derivatives of aromatic tertiary amines and styrylamine compounds, polysilane and the like.

The electron transport layer of the present invention is a known electron transport material, for example diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq ₃ , 2,5-diaryl silol derivative (PyPySPyPy), perfluorinated compound (PF -6P), Octasubstituted cyclooctatetraene compounds (COTs).

In the organic light emitting device of the present invention, the electron injection layer, the electron transport layer, the hole transport layer and the hole injection layer may be formed of a single layer containing one or more kinds of the above-mentioned compounds, or may be stacked on different kinds of compounds. It may consist of a plurality of layers to contain.

The light emitting layer of the organic electroluminescent device of the present invention may include a known light emitting material, for example, a phosphorescent fluorescent material, a fluorescent brightener, a laser dye, an organic scintillator and a reagent for fluorescence analysis. Specifically, a carbazole compound, a phosphine oxide compound, a carbazole-based phosphine oxide compound, bis (3,5-difluoro-4-cyanophenyl) pyridine, iridium picolinate (FCNIrpic), tris (8-hydroxyquinoline) aluminum Alq ₃ ), polyaromatic compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, 1,4- Bis (4-methylstyryl) benzene, 1,4-bis (4-methyl- Bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, 1,6- Liquid scintillation scintillators such as 3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, dicyanomethylenepyran dyes, dicyanomethylene Cyopyran pigment, polymethine pigment, oxobenzanthracene Pigments, xanthene pigments, carbostyryl pigments, perylene pigments, oxazine compounds, stilbene derivatives, spiro compounds, oxadiazole compounds and the like.

Each layer constituting the organic EL device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be manufactured using a material used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected according to the characteristics of the material, but may be determined usually in the range of 2 nm to 5,000 nm.

Since the compounds of Formulas 1 to 3 according to the present invention can be formed by a vacuum deposition method, there is an advantage that the thin film forming process is simple and can be easily obtained as a homogeneous thin film having little pin holes.

Hereinafter, the aromatic amine compound and the method of manufacturing the organic light emitting device including the same according to the present invention will be described in more detail with reference to Examples. However, this is for the purpose of illustration only and is not intended to limit the scope of the invention.

[Example]

An aromatic amine compound of the present invention was prepared, and an organic electroluminescent device was manufactured using this compound. The following Preparation Examples and Examples are intended to specifically illustrate the present invention, whereby the present invention should not be limited.

Manufacturing example  One. Chemical  Synthesis of 1

Synthesis of Intermediate 1

 4-amino-2,6-dichloropyridine (10.0 g, 61.4 mmol) bromobenzene (96.3 g, 614 mmol), palladium acetate (0.41 g, 1.84 mmol) and sodium t-butoxide (17.7 g, 184 mmol ) Was dissolved in anhydrous toluene. Tri-t-butylphosphine (1M toluene solution, 9.2 mL) was slowly added to the reaction solution under nitrogen atmosphere, followed by stirring under reflux for 24 hours. The reaction mixture was diluted with ethyl acetate and washed three times with distilled water. The organic layer was separated, the solvent was removed, and the residue was separated by column chromatography to obtain 15.0 g of Compound Intermediate 1.

¹ H NMR (500 MHz, CDCl ₃ ): δ 6.58 (s, 2H), 7.19 (d, 4H), 7.27 (t, 2H), 7.41 (t, 4H)

Synthesis of Compound 1

2,6-dichloro-N, N-diphenylpyridin-4-amine (1.2 g, 3.81 mmol), 3-biphenyl boronic acid (1.81 g, 9.12 mmol), tetrakis (triphenylphosphine) palladium (0) (0.26 g, 0.23 mmol) and THF (100 mL) were added to a two neck flask and nitrogen bubbled for 30 minutes. 30 mL (3.16 g) of degassed potassium carbonate solution was added thereto, and the mixture was stirred under reflux for 24 hours. The reaction solution was extracted with dichloromethane and distilled water, and the organic layer was separated and dried over magnesium sulfate. After the solvent was removed, column chromatography was separated using an ethyl acetate / hexane mixed solvent as a developing solvent, followed by vacuum drying to obtain 1.3 g of Compound 1.

¹ H NMR (500 MHz, CDCl ₃ ): δ 7.20 (t, 2H), 7.26 to 7.28 (m, 6H), 7.34 to 7.39 (m, 6H), 7.45 (t, 4H), 7.48 (t, 2H) , 7.60 (d, 2H), 7.64 (d, 4H), 7.89 (d, 2H), 8.24 (s, 2H).

MS (FAB) m / z 551 [(M + H) ⁺ ].

Manufacturing example  2. Chemical  Synthesis of 2

 2,6-dichloro-N, N-diphenylpyridin-4-amine (1.0 g, 3.17 mmol) and 3-biphenyl boronic acid were added to 3- (9H-carbazol-9-yl) phenyl boronic acid. Compound 2 was synthesized in the same manner as Compound 1 except that the compound was used as (2.19 g, 7.61 mmol) to obtain 2.0 g of a white solid.

¹ H NMR (500 MHz, CDCl ₃ ): δ 7.19 (t, 2H), 7.21-7.31 (m, 14H), 7.35 (t, 4H), 7.41 (d, 4H), 7.54 (d, 2H), 7.60 (t, 2H), 7.98 (d, 2H), 8.12 (d, 4H), 8.17 (s, 2H)

MS (FAB) m / z 729 [(M + H) ⁺ ].

Manufacturing example  3. Synthesis of Compound 3

 2,6-dichloro-N, N-diphenylpyridin-4-amine (1.5 g, 4.76 mmol) and 3-biphenyl boronic acid were converted to dibenzofuran-2-yl boronic acid (2.42 g, 11.4 mmol). ), And Compound 3 was synthesized in the same manner as in Compound 1 to obtain 1.6 g of a white solid.

¹ H NMR (500 MHz, CDCl ₃ ): δ 7.24 (t, 2H), 7.31 (s, 2H), 7.32 (d, 4H), 7.35 (t, 2H), 7.41 (t, 4H), 7.46 (t , 2H), 7.57 (d, 2H), 7.61 (d, 2H), 8.03 (d, 2H), 8.07 (d, 2H), 8.62 (s, 2H)

MS (FAB) m / z 579 [(M + H) ⁺ ].

Manufacturing example  4. Synthesis of Compound 4

Synthesis of Intermediate 2

4-amino-2,6-dichloropyridine (3.0 g, 18.4 mmol), bromobenzene (31.5 g, 184 mmol), palladium acetate (0.12 g, 0.55 mmol) and sodium t-butoxide (5.3 g, 55.2 mmol) was dissolved in anhydrous toluene. Tri-t-butylphosphine (1M toluene solution, 2.8 mL) was slowly added to the reaction solution under nitrogen atmosphere, followed by stirring under reflux for 24 hours. The reaction mixture was diluted with ethyl acetate and washed three times with distilled water. The organic layer was separated, the solvent was removed, and the residue was separated by column chromatography to obtain 3.9 g of Compound Intermediate 2.

¹ H NMR (500 MHz, CDCl ₃ ): δ 2.31 (s, 6H), 6.56 (s, 2H), 7.18 (d, 4H), 7.39 (t, 4H)

Synthesis of Compound 4

Intermediate 2 (1.5g, 4.37 mmol), 3-biphenyl boronic acid (2.08 g, 10.5 mmol), tetrakis (triphenylphosphine) palladium (0) (0.30g, 0.26mmol) and THF (45 mL) Was added to a two-necked flask and nitrogen bubbled for 30 minutes. 15 mL (3.62 g) of degassed potassium carbonate solution was added thereto, and the mixture was stirred under reflux for 24 hours. The reaction solution was extracted with dichloromethane and distilled water, and the organic layer was separated and dried over magnesium sulfate. After the solvent was removed, column chromatography was separated using an ethyl acetate / hexane mixed solvent as a developing solvent, followed by vacuum drying to obtain 1.5 g of Compound 4.

¹ H NMR (500 MHz, CDCl ₃ ): δ 2.3 (s, 6H), 7.26-7.28 (m, 6H), 7.34-7.39 (m, 6H), 7.45 (t, 4H), 7.48 (t, 2H) , 7.60 (d, 2H), 7.64 (d, 4H), 7.89 (d, 2H), 8.24 (s, 2H).

MS (FAB) m / z 580 [(M + H) ⁺ ].

Manufacturing example  5. Chemical  Synthesis of 5

Synthesis of Intermediate 3

Aniline (1.0 g, 10.7 mmol), 2,6-dichloro-4-iodopyridine (8.82 g, 32.2 mmol), palladium acetate (0.12 g, 0.54 mmol) and sodium t-butoxide (3.10 g, 32.2 mmol ) Was dissolved in anhydrous toluene. Tri-t-butylphosphine (1M toluene solution, 2.7 mL) was slowly added to the reaction solution under a nitrogen atmosphere, followed by stirring under reflux for 24 hours. The reaction mixture was diluted with ethyl acetate and washed three times with distilled water. The organic layer was separated, the solvent was removed, and the residue was separated by column chromatography to obtain 3.3 g of compound intermediate 3.

¹ H NMR (500 MHz, CDCl ₃ ): δ 6.72 (s, 4H), 7.28 (d, 2H), 7.32 (t, 1H), 7.45 (t, 2H)

Synthesis of Compound 5

Intermediate 3 (1.0 g, 2.60 mmol), 3-biphenyl boronic acid (2.57 g, 13.0 mmol), tetrakis (triphenylphosphine) palladium (0) (0.30 g, 0.26 mmol) and THF (100 mL) Was added to a two-necked flask and nitrogen bubbled for 30 minutes. 30 mL (3.59 g) of degassed potassium carbonate solution was added thereto, and the mixture was stirred under reflux for 24 hours. The reaction solution was extracted with dichloromethane and distilled water, and the organic layer was separated and dried over magnesium sulfate. After the solvent was removed, column chromatography was separated using an ethyl acetate / hexane mixed solvent as a developing solvent, followed by vacuum drying to obtain 1.3 g of Compound 1.

¹ H NMR (500 MHz, CDCl ₃ ): δ 7.28 (t, 1H), 7.31-7.45 (m, 20H), 7.48 (t, 4H), 7.58 (d, 4H), 7.62 (d, 8H), 7.88 (d, 4H), 8.30 (s, 4H).

MS (FAB) m / z 857 [(M + H) ⁺ ].

Manufacturing example  6. Synthesis of Compound 21

Synthesis of Intermediate 4

4-amino-2,6-dichloropyridine (3.0 g, 18.4 mmol), 2,6-dichloro-4-iodopyridine (15.1 g, 55.2 mmol), palladium acetate (0.21 g, 0.92 mmol) and sodium t-butoxide (5.3 g, 55.2 mmol) was dissolved in anhydrous toluene. Tri-t-butylphosphine (1 M toluene solution, 4.6 mL) was slowly added to the reaction solution under a nitrogen atmosphere, followed by stirring under reflux for 24 hours. The reaction mixture was diluted with ethyl acetate and washed three times with distilled water. The organic layer was separated, the solvent was removed, and the residue was separated by column chromatography to obtain 3.7 g of Compound Intermediate 4.

¹ H NMR (500 MHz, CDCl ₃ ): δ 6.67 (s, 6H)

Synthesis of Compound 21

Intermediate 4 (2.0 g, 4.4 mmol), phenyl boronic acid (4.8 g, 39.6 mmol), tetrakis (triphenylphosphine) palladium (0) (0.91 g, 0.79 mmol) and THF (150 mL) The flask was charged with nitrogen for 30 minutes. 50 mL of degassed potassium carbonate solution (10.9 g of potassium carbonate) was added thereto, and the mixture was stirred under reflux for 24 hours. The reaction solution was extracted with dichloromethane and distilled water, and the organic layer was separated and dried over magnesium sulfate. After the solvent was removed, column chromatography was separated using an ethyl acetate / hexane mixed solvent as a developing solvent, followed by vacuum drying to obtain 1.2 g of Compound 21.

¹ H NMR (500 MHz, CDCl ₃ ): δ 7.45 (t, 12H), 7.49 (t, 6H), 7.66 (d, 12H), 8.29 (s, 6H).

MS (FAB) m / z 706 [(M + H) ⁺ ].

Example  One

Compound 1 synthesized in the present invention was applied as a light emitting host material of a blue phosphor to prepare a blue phosphor. The structure of the device was ITO / DNTPD / NPB / mCP / Compound 1: FIrpic / TSPO1 / LiF / Al.

 The abbreviations and names of the materials used in the device are as follows: ITO; Indium tin oxide, DNTPD; N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl ] -biphenyl-4,4'-diamine, NPB; (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine), mCP; N, N-dicarbazolyl-3,5-benzene, FIrpic; Bis (4,6-difluorophenylpyridinato-N, C2) picolinatoiridium, TSPO1; diphenylphosphine oxide-4- (triphenylsilyl) phenyl.

Fabrication of the device was performed in the following manner.

The ITO substrate was cleaned with pure water and isopropyl alcohol for 30 minutes in ultrasonic waves, and the ITO substrate was surface treated with short wavelength ultraviolet light, and then the organic material was vacuum deposited under a pressure of ¹ × 10 ⁻⁶ torr. Common layer materials DNTPD, NPB, mCP, and TSPO1 were deposited at a rate of 0.1 nm / s to form films corresponding to each thickness. Compound 1, a blue phosphorescent host material, was vacuum deposited simultaneously with FIrpic, a phosphorescent dopant material. The deposition rate was 0.1 nm / s for mCP and 0.015 nm / s for FIrpic. LiF was formed at a thickness of 1 nm at a rate of 0.01 nm / s, and Al was formed at a thickness of 100 nm at a deposition rate of 0.5 nm / sec. After the device was formed, the device was sealed using a CaO absorbent and a glass cover glass.

Applying Compound 1 as a light emitting host material of a blue phosphor, X = 0.15 and y = 0.31 based on 14.0% of quantum efficiency, 24.3 cd / A of current efficiency, 16.9 lm / W of power efficiency, and CIE 1931 color coordinates at a voltage of 5V. It showed excellent blue phosphorescence properties.

Example  2

Compound 2 synthesized in the present invention was applied as a blue phosphorescent host material to fabricate an organic EL device.

The structure of the device was ITO / DNTPD / NPB / mCP / Compound 2: FIrpic / TSPO1 / LiF / Al. The fabrication process of the device was the same as that in Example 1 except that Compound 2 was applied to the blue host material.

Applying Compound 2 as a light emitting host material of a blue phosphor, x = 0.15 and y = 0.32 based on quantum efficiency of 15.6%, current efficiency of 27.5 cd / A, power efficiency of 19.1 lm / W, and CIE 1931 color coordinates at a voltage of 5V. It showed excellent blue phosphorescence properties.

Example  3

Compound 3 synthesized in the present invention was applied as a blue phosphorescent host material to fabricate an organic EL device.

The structure of the device was ITO / DNTPD / NPB / mCP / Compound 3: FIrpic / TSPO1 / LiF / Al. The fabrication process of the device was the same as that in Example 1 except that Compound 3 was applied to the blue host material.

Applying Compound 3 as a light emitting host material of a blue phosphor, x = 0.14 and y = 0.31 based on 16.1% of quantum efficiency, 27.8 cd / A of current efficiency, 19.3 lm / W of power efficiency, and CIE 1931 color coordinates at a voltage of 5V. It showed excellent blue phosphorescence properties.

Example  4

Compound 1 synthesized in the present invention was applied as a light emitting layer host material of a blue phosphorescent device, and compound 21 was applied as an electron transporting layer material to fabricate an organic light emitting device. The structure of the device was ITO / DNTPD / NPB / mCP / Compound 1: FIrpic / Compound 21 / LiF / Al. The fabrication process of the device was the same as in Example 1 except that the electron transport layer material was applied to Compound 21.

Compound 1 and Compound 21 were applied as the light emitting layer host and the electron transporting layer material of the blue phosphor, respectively, based on quantum efficiency of 18.1%, current efficiency of 35.9 cd / A, power efficiency of 22.7 lm / W, and CIE 1931 color coordinates at a voltage of 5V. x = 0.16 and y = 0.38 showed excellent blue phosphorescence properties.

Comparative Example  One

In order to compare the characteristics of the compound synthesized in the present invention, an organic light emitting diode was manufactured by applying mCP as a blue phosphorescent host material.

The structure of the device was ITO / DNTPD / NPB / mCP / mCP: FIrpic / TSPO1 / LiF / Al. The fabrication process of the device was the same as that of Example 1 except that mCP was applied to the blue host material.

The mCP and TSPO1 are applied as the light emitting host and the electron transporting layer material of the blue phosphor, respectively, and x = 5 = quantum efficiency 13.8%, current efficiency 25.2 cd / A, power efficiency 17.5 lm / W and CIE 1931 color coordinates at a voltage of 5V. 0.16, y = 0.34.

The quantum efficiencies of Examples 1 to 4 and Comparative Example 1 are described in G. Gu and SR Forrest, IEEE Journal of Selected Topics in Quantum Electronics, Vol. 4, No. 1, January / February 1998, p. 83-99 Measurement as described in

Referring to FIG. 3, an absorption spectrum, a solution (THF) emission spectrum, a solid emission spectrum, and a low temperature emission spectrum of Compound 2 are shown. As shown in FIG. 3, the maximum fluorescence emission wavelength of Compound 2 was 421 nm in the solution. In particular, the phosphorescence emission wavelength was observed at 449 nm in the low temperature emission spectrum, and the triplet energy was confirmed to be 2.76 eV. It is therefore possible to use blue or green phosphorescent host materials.

Claims (19)

An aromatic amine compound for organic electroluminescent devices represented by Structural Formula 1 below.
[Structural formula 1]

In the above formula 1,
Ring a is an aromatic ring having 5 to 7 nuclear atoms and having 1 to 3 nitrogen atoms in the nuclear atom,
R ¹ to R ³ may be the same as or different from each other, R ¹ to R ³ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring a heteroaryl group, or, it is possible to form a bonding heteroaromatic ring of C _{6 -30} bonded aromatic ring or C _{2 -30} with the combination with the carbon atom of the adjacent benzene ring,
R ⁴ to R ⁸ may be the same or different from each other, R ⁴ to R ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted heteroaryl group or a C _{2 -30,} conjugated aromatic C _6-30 together in combination with the carbon atom of the adjacent benzene ring or ring may form a conjugated heteroaromatic ring of C _{2 -30,}
Ar ¹ to Ar ⁴ may be the same or different from each other, Ar ¹ to Ar ⁴ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or hetero-substituted or unsubstituted C _{2 -30} Exchange An aryl group,
Y ¹ is an oxygen atom or a sulfur atom,
Ar ¹ to Ar ⁴ and R ¹ to R groups for "substituted" in ⁸ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of. The method of claim 1,
R ¹ to R ³ may be the same as or different from each other, R ¹ to R ³ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -6} ring,
And R ⁴ to R ⁸ may be the same or different from each other, R ⁴ to R ⁸ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -6} ring,
Ar ¹ to Ar ⁴ may be the same or different from each other, and, Ar ¹ to Ar ⁴ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted C _{2 -14} heteroaryl Gigi,
Y ¹ is an aromatic amine compound, characterized in that an oxygen atom or a sulfur atom. 3. The method of claim 2,
R ¹ to R ³ may be the same as or different from each other, R ¹ to R ³ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -3} ring,
And R ⁴ to R ⁸ may be the same or different from each other, R ⁴ to R ⁸ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -3} ring,
Ar ¹ to Ar ⁴ may be the same or different from each other, and, Ar ¹ to Ar ⁴ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -10} aryl group or a substituted or unsubstituted C _{2 -10} heteroaryl Gigi,
Y ¹ is an oxygen atom, characterized in that an aromatic amine compound. The method of claim 3,
R ¹ to R ³ may be the same as or different from each other, R ¹ to R ³ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -3} ring,
And R ⁴ to R ⁸ may be the same or different from each other, R ⁴ to R ⁸ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -3} ring,
Ar ¹ to Ar ⁴ may be the same as or different from each other, Ar ¹ to Ar ⁴ are each independently a hydrogen atom or a phenyl group,
Y ¹ is an oxygen atom, characterized in that an aromatic amine compound. An aromatic amine compound for organic electroluminescent devices represented by the following Structural Formula 2.
[Structural formula 2]

In the above formula 2,
Ring b and ring c may be the same as or different from each other, ring b and ring c are each independently an aromatic ring having 5 to 7 nuclear atoms and 1 to 3 nitrogen atoms in the nuclear atom,
R ⁹ to R ¹¹ may be the same as or different from each other, R ⁹ to R ¹¹ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring a heteroaryl group, or, it is possible to form a bonding heteroaromatic ring of C _{6 -30} bonded aromatic ring or C _{2 -30} with the combination with the carbon atom of the adjacent benzene ring,
R ¹² to R ¹⁶ may be the same or different from each other, R ¹² to R ¹⁶ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted heteroaryl group or a C _{2 -30,} combines with the carbon atom of the adjacent benzene ring bonding with the aromatic ring of C _{6 -30} or may form a conjugated heteroaromatic ring of C _{2 -30,}
Ar ⁵ to Ar ⁸ may be the same or different from each other, Ar ⁵ to Ar ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or hetero-substituted or unsubstituted C _{2 -30} An aryl group,
Y ² is an oxygen atom or a sulfur atom,
Ar ⁵ to Ar ⁸ and R ⁹ to R groups for "substituted" at ¹⁶ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of. The method of claim 5,
R ⁹ to R ¹¹ may be the same as or different from each other, R ⁹ to R ¹¹ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -6} ring,
And R ¹² to R ¹⁶ may be the same or different from each other, R ¹² to R ¹⁶ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -6} ring,
Ar ⁵ to Ar ⁸ may be the same or different from each other, Ar ⁵ to Ar ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted C _{2 -14} heteroaryl Gigi,
Y ² is an aromatic amine compound, characterized in that an oxygen atom or a sulfur atom. The method according to claim 6,
R ⁹ to R ¹¹ may be the same as or different from each other, R ⁹ to R ¹¹ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -3} ring,
And R ¹² to R ¹⁶ may be the same or different from each other, R ¹² to R ¹⁶ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -3} ring,
Ar ⁵ to Ar ⁸ may be the same or different from each other, Ar ⁵ to Ar ⁸ each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -10} aryl group or a substituted or unsubstituted C _{2 -10} heteroaryl Gigi,
Y ² is an oxygen atom, characterized in that an aromatic amine compound. The method of claim 7, wherein
R ⁹ to R ¹¹ may be the same as or different from each other, R ⁹ to R ¹¹ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -3} ring,
And R ¹² to R ¹⁶ may be the same or different from each other, R ¹² to R ¹⁶ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -3} ring,
Ar ⁵ to Ar ⁸ may be the same as or different from each other, Ar ⁵ to Ar ⁸ are each independently a hydrogen atom or a phenyl group,
Y ² is an oxygen atom, characterized in that an aromatic amine compound. An aromatic amine compound for organic electroluminescent devices represented by Structural Formula 3 below.
[Structural Formula 3]

In the above formula 3,
Ring d, ring e and ring f may be the same or different from each other, and ring d, ring e and ring f each independently have 5 to 7 nuclear atoms, and aromatic rings having 1 to 3 nitrogen atoms in the nuclear atoms ego,
R ¹⁷ to R ¹⁹ may be the same as or different from each other, R ¹⁷ to R ¹⁹ are each independently a hydrogen atom,

,

,

,

,

, A substituted or unsubstituted C _{1 -9} alkyl group, a substituted or unsubstituted C _{5 -30} alkyl group, a substituted or unsubstituted C _{6 -30} aryl group or a substituted or unsubstituted C _{2 -30} of the ring of the ring a heteroaryl group, or, it is possible to form a bonding heteroaromatic ring of C _{6 -30} bonded aromatic ring or C _{2 -30} with the combination with the carbon atom of the adjacent benzene ring,
R ²⁰ to R ²⁴ may be the same or different from each other, R ²⁰ to R ²⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of C _{1 -9} ring, a substituted or unsubstituted alkyl ventilation of _{5 -30} C ring, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted heteroaryl group or a C _{2 -30,} combines with the carbon atom of the adjacent benzene ring bonding with the aromatic ring of C _{6 -30} or may form a conjugated heteroaromatic ring of C _{2 -30,}
Ar ⁹ through Ar ¹² may be the same or different from each other, each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group or a substituted heteroaryl or unsubstituted C _{2 -30} aryl group,
Y ³ is an oxygen atom or a sulfur atom,
Ar ⁹ to Ar ¹² and R ¹⁷ to group for the "substituted" in R ²⁴ may be the same as or different from each other, and each independently represent a group of a halogen atom, a cyano group, a nitro group, an aryl group of _{5 -30} C, ₂ C a heteroaryl group of _-30, a silyl group of the alkyl group of C _{1 -9,} alkyl ventilation of C _5-30, C _{1 -30} thio, or C _{1 -30} of. 10. The method of claim 9,
R ¹⁷ to R ¹⁹ may be the same as or different from each other, R ¹⁷ to R ¹⁹ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -6} ring,
R ²⁰ to R ²⁴ may be the same or different from each other, and R ²⁰ to R ²⁴ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -6} ring,
Ar ⁹ through Ar ¹² may be the same or different from each other, Ar ⁹ to Ar ¹² each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -14} aryl group or a substituted or unsubstituted C _{2 -14} heteroaryl Gigi,
Y ³ is an aromatic amine compound, characterized in that an oxygen atom or a sulfur atom. The method of claim 10,
R ¹⁷ to R ¹⁹ may be the same as or different from each other, R ¹⁷ to R ¹⁹ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -3} ring,
R ²⁰ to R ²⁴ may be the same or different from each other, and R ²⁰ to R ²⁴ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -3} ring,
Ar ⁹ through Ar ¹² may be the same or different from each other, Ar ⁹ to Ar ¹² each independently represent a hydrogen atom, a substituted or unsubstituted C _{6 -10} aryl group or a substituted or unsubstituted C _{2 -10} heteroaryl Gigi,
Y ³ is an oxygen atom, characterized in that an aromatic amine compound. 12. The method of claim 11,
R ¹⁷ to R ¹⁹ may be the same as or different from each other, R ¹⁷ to R ¹⁹ are each independently a hydrogen atom,

,

,

,

,

And, an alkyl group or a substituted or unsubstituted C _{1 -3} ring,
R ²⁰ to R ²⁴ may be the same or different from each other, and R ²⁰ to R ²⁴ each independently represents a hydrogen atom or a substituted or unsubstituted C _{1 -3} ring,
Ar ⁹ to Ar ¹² may be the same as or different from each other, Ar ⁹ to Ar ¹² are each independently a hydrogen atom or a phenyl group,
Y ³ is an oxygen atom, characterized in that an aromatic amine compound. A first electrode; A second electrode; And an organic material layer between the first electrode and the second electrode.
The organic material layer of the organic light emitting device, characterized in that it comprises an aromatic amine compound according to any one selected from claim 1, 5 and 9. The method of claim 13,
The organic material layer is an organic light emitting device, characterized in that the light emitting layer. The method of claim 13,
The organic material layer is an organic light emitting device, characterized in that the hole transport layer. The method of claim 13,
The organic material layer is an organic light emitting device, characterized in that the hole injection layer. The method of claim 13,
The organic material layer is an organic light emitting device, characterized in that the electron transport layer. The method of claim 13,
The organic material layer is an organic light emitting device, characterized in that the electron injection layer. A first electrode; A second electrode; And a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer includes a host and a dopant.
The host of claim 1, 5 and 9 characterized in that it comprises an aromatic amine compound according to any one selected from the organic electroluminescent device.

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