KR101554680B1 - Aromatic amine compound and organic electroluminescent device including the same - Google Patents

Abstract

The present invention relates to an aromatic amine compound and an organic electroluminescent device including the same. The present invention relates to an aromatic amine compound and an organic electroluminescent device including the same, which exhibit an excellent quantum efficiency as compared with a conventional organic electroluminescent compound, An aromatic amine compound and an organic electroluminescent device including the same are provided.

Description

TECHNICAL FIELD [0001] The present invention relates to an aromatic amine compound and an organic electroluminescent device including the same. BACKGROUND ART [0002]

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

The organic electroluminescent device has a simpler structure than other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP) and a field emission display (FED) And has a high response speed and a low driving voltage, so that it is being actively developed to be used as a light source for a flat panel display such as a wall-mounted TV or a backlight of a display, a lighting, and a billboard.

In general, when a direct current voltage is applied to an organic electroluminescent device, holes injected from the anode recombine with electrons injected from the cathode to form an electron-hole pair exciton, and the exciton returns to a stable ground state, It is converted into light by transmission to the material.

In order to improve the efficiency and stability of the organic electroluminescent device, a laminated organic thin film is formed between two opposing electrodes by CW Tang et al. Of Eastman Kodak Company, and a low voltage driven organic electroluminescent device is reported (CW Tang, SA Vanslyke, Applied Physics Letters, vol. 51, p. 913, 1987), studies on organic materials for multilayer thin film structure organic electroluminescent devices have been actively conducted. The efficiency and lifetime of such a stacked organic electroluminescent device are closely related to the molecular structure of the material constituting 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.

A variety of compounds are known as conventional arylamine-based compounds and have been used as a hole-transporting layer material or a light-emitting layer doping material for hole transporting properties and luminescent properties. However, when used as a light emitting host material, the hole mobility is very large compared to the electron mobility, and thus an additional lamination structure such as a hole blocking layer is required, which complicates the process. There is a problem that it is difficult to use it as a host material for a light-emitting layer because of its strong electron-donating property.

SUMMARY OF THE INVENTION Accordingly, the present invention has been made in view of the above problems, and it is an object of the present invention to provide an organic electroluminescent device and a method for manufacturing the same, The present invention provides an aromatic amine compound having improved driving voltage when applied to a device and exhibiting excellent quantum efficiency, power efficiency and current efficiency.

A second object of the present invention is to provide an organic electroluminescent device including 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 electroluminescence device represented by the following structural formula (1).

[Structural formula 1]

 In the above formula 1,

The ring a is 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 ¹ to R ³ may be the same or different from each other, and 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, preferably a hydrogen atom,

,

,

,

,

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

,

,

,

,

, Or a substituted or unsubstituted C _{1 -3} alkyl group, or may combine with the carbon atoms of adjacent benzene rings to form a covalently bonded aromatic ring of C _{6 -30} or a fused heteroaromatic ring of C _{2 -30} However,

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 -C ₃₀ aryl group or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, preferably a hydrogen atom or a substituted or unsubstituted C _{1 -6} alkyl group, A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or may combine with the carbon atoms of adjacent benzene rings to form a covalently bonded aromatic ring of C _{6 -30} or a fused heteroaromatic ring of C _{2 -30} 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 a substituted or unsubstituted C _{2 -30} hetero 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 aspect of the present invention provides an aromatic amine compound for an organic electroluminescence 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 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_1-9의 알킬기, 치환 또는 비치환된 C_5-30의 알킬환기, 치환 또는 비치환된 C_6-30의 아릴기, 또는 치환 또는 비치환된 C_2-30의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-6의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-3의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_6-30의 접합된 방향족 고리 또는 C_2-30의 접합된 헤테로 방향족 고리를 형성할 수 있고,R ⁹ to R ¹¹ , R ^{10 '} , and R ^11' may be the same or different from each other, and R ⁹ to R ¹¹ , R ^{10 '} , and R ^11'

,

,

,

,

, 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 A heteroaryl group, preferably a hydrogen atom,

,

,

,

,

, Or a substituted or unsubstituted C _1-6 alkyl group, more preferably a hydrogen atom,

,

,

,

,

, Or a substituted or unsubstituted C _1-3 alkyl group, or may combine with the carbon atoms of neighboring benzene rings to form a C _6-30 fused aromatic ring or a C _2-30 fused heteroaromatic ring However,

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 -C ₃₀ aryl group or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, preferably a hydrogen atom or a substituted or unsubstituted C _1-6 alkyl group, more preferably a A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or may combine with the carbon atoms of adjacent benzene rings to form a covalently bonded aromatic ring of C _{6 -30} or a fused heteroaromatic ring of C _{2 -30} 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.

 Another embodiment of the present invention provides an aromatic amine compound for an organic electroluminescence device represented by the following structural formula (3).

[Structural Formula 3]

In the above formula 3,

The ring d, the ring e and the ring f may be the same or different from each other, and the ring d, the ring e and the ring f are each independently an aromatic ring having 5 to 7 nuclear atoms and having 1 to 3 nitrogen atoms ego,

,

,

,

,

, 치환 또는 비치환된 C_1-9의 알킬기, 치환 또는 비치환된 C_5-30의 알킬환기, 치환 또는 비치환된 C_6-30의 아릴기, 또는 치환 또는 비치환된 C_2-30의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-6의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-3의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_6-30의 접합된 방향족 고리 또는 C_2-30의 접합된 헤테로 방향족 고리를 형성할 수 있고, R ¹⁷ to ^{R 19, R 17 ', R} 18', and R ^{19 'may} be the same or different from each other, R ¹⁷ to ^{R 19, R 17', R} 18 ', and 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 A heteroaryl group, preferably a hydrogen atom,

,

,

,

,

, Or a substituted or unsubstituted C _1-6 alkyl group, more preferably a hydrogen atom,

,

,

,

,

, Or a substituted or unsubstituted C _1-3 alkyl group, or may combine with the carbon atoms of neighboring benzene rings to form a C _6-30 fused aromatic ring or a C _2-30 fused heteroaromatic ring However,

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 -C ₃₀ aryl group or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, preferably a hydrogen atom or a substituted or unsubstituted C _1-6 alkyl group, more preferably a A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or may combine with the carbon atoms of adjacent benzene rings to form a covalently bonded aromatic ring of C _{6 -30} or a fused heteroaromatic ring of C _{2 -30} Can,

Ar ⁹ to Ar ¹² may be the same or different from each other and each independently represents a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted C _{2 -30} heteroaryl group, 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.

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode; And an organic material layer between the first electrode and the second electrode, the organic electroluminescent device comprising:

Wherein the organic material layer comprises an 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 transporting 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 transporting layer.

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

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode; And a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer comprises a host and a dopant,

The organic electroluminescent device of the present invention comprises the aromatic amine compound according to the present invention.

The present invention relates to an organic electroluminescent device having improved driving voltage and excellent quantum efficiency, power efficiency and current efficiency when applied to a hole transport material, a hole injecting material, a light emitting layer material, a host material of a light emitting layer, an electron transporting material, ≪ / RTI > can be provided.

The present invention also provides an organic electroluminescent device comprising an aromatic amine compound having a low driving voltage and high quantum efficiency, power efficiency and current efficiency.

FIG. 1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention. Referring to FIG.
2 is a schematic cross-sectional view of an organic electroluminescent device according to another embodiment of the present invention.
FIG. 3 is a diagram showing an absorption spectrum, a solution (THF) emission spectrum, a solid emission spectrum and a low temperature emission spectrum of Compound 2. FIG.

Hereinafter, preferred embodiments of an aromatic amine compound for an organic electroluminescence device and an organic electroluminescence device including the same will be described in detail with reference to the drawings and the accompanying drawings, wherein like reference numerals refer to like or corresponding components Elements are denoted by the same reference numerals, and redundant description thereof will be omitted.

It is to be understood, however, that the following description is not intended to limit the invention to the particular embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the 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 >

The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

As one of technical means for achieving the above technical object, one aspect of the present invention provides an aromatic amine compound for an organic electroluminescence element represented by the following structural formula (1).

[Structural formula 1]

In the above formula 1,

The ring a is an aromatic ring having 5 to 7 nuclear atoms and 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 or different from each other, and 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 A heteroaryl group, preferably a hydrogen atom,

,

,

,

,

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

,

,

,

,

, Or a substituted or unsubstituted C _{1 -3} alkyl group, or may combine with the carbon atoms of adjacent benzene rings to form a covalently bonded aromatic ring of C _{6 -30} or a fused heteroaromatic ring of C _{2 -30} However,

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 -C ₃₀ aryl group or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, preferably a hydrogen atom or a substituted or unsubstituted C _{1 -6} alkyl group, A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or may combine with the carbon atoms of adjacent benzene rings to form a covalently bonded aromatic ring of C _{6 -30} or a fused heteroaromatic ring of C _{2 -30} 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 a substituted or unsubstituted C _{2 -30} hetero 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 aspect of the present invention provides an aromatic amine compound for an organic electroluminescence 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 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_1-9의 알킬기, 치환 또는 비치환된 C_5-30의 알킬환기, 치환 또는 비치환된 C_6-30의 아릴기, 또는 치환 또는 비치환된 C_2-30의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-6의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-3의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_6-30의 접합된 방향족 고리 또는 C_2-30의 접합된 헤테로 방향족 고리를 형성할 수 있고,R ⁹ to R ¹¹ , R ^{10 '} , and R ^11' may be the same or different from each other, and R ⁹ to R ¹¹ , R ^{10 '} , and R ^11'

,

,

,

,

, 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 A heteroaryl group, preferably a hydrogen atom,

,

,

,

,

, Or a substituted or unsubstituted C _1-6 alkyl group, more preferably a hydrogen atom,

,

,

,

,

, Or a substituted or unsubstituted C _1-3 alkyl group, or may combine with the carbon atoms of neighboring benzene rings to form a C _6-30 fused aromatic ring or a C _2-30 fused heteroaromatic ring However,

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 -C ₃₀ aryl group or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, preferably a hydrogen atom or a substituted or unsubstituted C _1-6 alkyl group, more preferably a A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or may combine with the carbon atoms of adjacent benzene rings to form a covalently bonded aromatic ring of C _{6 -30} or a fused heteroaromatic ring of C _{2 -30} 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.

 Another embodiment of the present invention provides an aromatic amine compound for an organic electroluminescence device represented by the following structural formula (3).

[Structural Formula 3]

In the above formula 3,

The ring d, the ring e and the ring f may be the same or different from each other, and the ring d, the ring e and the ring f are each independently an aromatic ring having 5 to 7 nuclear atoms and having 1 to 3 nitrogen atoms ego,

,

,

,

,

, 치환 또는 비치환된 C_1-9의 알킬기, 치환 또는 비치환된 C_5-30의 알킬환기, 치환 또는 비치환된 C_6-30의 아릴기, 또는 치환 또는 비치환된 C_2-30의 헤테로 아릴기, 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-6의 알킬기, 보다 바람직하게는 수소원자,

,

,

,

,

, 또는 치환 또는 비치환된 C_1-3의 알킬기이거나, 이웃한 벤젠고리의 탄소원자와 결합하여 함께 C_6-30의 접합된 방향족 고리 또는 C_2-30의 접합된 헤테로 방향족 고리를 형성할 수 있고, R ¹⁷ to ^{R 19, R 17 ', R} 18', and R ^{19 'may} be the same or different from each other, R ¹⁷ to ^{R 19, R 17', R} 18 ', and 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 A heteroaryl group, preferably a hydrogen atom,

,

,

,

,

, Or a substituted or unsubstituted C _1-6 alkyl group, more preferably a hydrogen atom,

,

,

,

,

, Or a substituted or unsubstituted C _1-3 alkyl group, or may combine with the carbon atoms of neighboring benzene rings to form a C _6-30 fused aromatic ring or a C _2-30 fused heteroaromatic ring However,

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 -C ₃₀ aryl group or a substituted or unsubstituted C ₂ -C ₃₀ heteroaryl group, preferably a hydrogen atom or a substituted or unsubstituted C _1-6 alkyl group, more preferably a A hydrogen atom or a substituted or unsubstituted C _{1 -3} alkyl group, or may combine with the carbon atoms of adjacent benzene rings to form a covalently bonded aromatic ring of C _{6 -30} or a fused heteroaromatic ring of C _{2 -30} Can,

Ar ⁹ to Ar ¹² may be the same or different from each other and each independently represents a hydrogen atom, a substituted or unsubstituted C _{6 -30} aryl group, or a substituted or unsubstituted C _{2 -30} heteroaryl group, 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 specific examples of the C ₆ -C ₃₀ aryl group of Ar ¹ to Ar ¹² include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, Naphthacene group, 9-naphthacene group, 1-naphthacenyl group, 1-naphthacenyl group, 2-naphthacenyl group, , A p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl group, An o-tolyl group, an m-tolyl group, a p-tolyl group, a p-tolyl group, a p- methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4-methylbiphenyl group, 4-tert-butyl-p-terphenyl-4-yl group and the like.

The above R ¹ to R ²⁴ And specific examples of the C _{2 -30} heteroaryl group of Ar ¹ to Ar ¹² include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, pyrimidyl, Indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group Isoindolinyl, 3-isoindolinyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2- furyl, 3- A benzofuranyl group, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranyl group, Isobenzofuranyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 3-isobenzofuransulfonyl group, A diazo group, a 6-dibenzofuranyl group, a 7-dibenzo Benzothiophene, 6-benzothiophene, 6-benzothiophene, 7-benzothiophene, 2-benzothiophene, Dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 6-dibenzothiophene, 7-dibenzothiophene, 8-dibenzothiophene, Benzophenone, benzothiophene, octane, octene, 9-dibenzothiophene, 2-benzofospor, 3-benzophosphole, Dibenzofospor, 8-dibenzofospor, 9-iben zofospor, 2-dibenzofospor, 3-dibenzofospor, 4- Benzophenes such as benzoyl peroxide, benzoyl peroxide, benzoyl peroxide, benzoyl peroxide, benzoyl peroxide, benzoyl peroxide, benzoyl peroxide, benzoyl peroxide, Dibenzo phosphoxide, 3-di Dibenzo phosphoxide, 8-dibenzo phosphoxide, 9-dibenzo phosphoxide, quinolyl, 3- (4-dibenzoyl) phospholene, Quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-quinolyl group, 4-quinolyl group, Isoquinolinyl group, 5-isoquinolinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, , 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, Acridine group, 9-acridine group, 9-acridine group, 1-acridine group, 1-acridine group, 1-acridine group, , A 7-phenanthroline-2-yl group, a 1,7-phenanthroline-3-yl group, a 1,7-phenanthroline- Yl group, a 1,7-phenanthroline-8-yl group, a 1,7-phenanthroline-9-yl group, a 1,7-phenanthroline- Dienes, 1,8-phenanthroline-2-yl groups, 1,8-phenanthroline-3-yl groups, 1,8-phenanthroline- A 1,8-phenanthroline-6-yl group, a 1,8-phenanthroline-7-yl group, a 1,8-phenanthroline- A 1,9-phenanthroline-4-yl group, a 1,9-phenanthroline-5-yl group, a 1,9-phenanthroline- 6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline- Phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group, 2,9-phenanthrol Yl group, a 2,9-phenanthroline-4-yl group, a 2,9-phenanthroline-5-yl group, a 2,9-phenanthroline- 6-yl group, 2,9-phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline- Yl group, a 2,8-phenanthroline-5-yl group, a 2,8-phenanthroline-3-yl group, 6-yl group, 2,8-phenanthroline-7-yl group, 2,8-phenanthroline-9-yl group, 2,8-phenanthrolineyl group, 2,7- , 2,7-phenanthroline-5-yl group, 2,7-phenanthroline-6-yl group, 2,7-phenanthroline- A phenanthroline-8-yl group, a 2,7-phenanthroline-9-yl group, a 2,7-phenanthroline-10-yl group, A 2-phenothiazyl group, a 3-phenothiazyl group, a 4-phenothiazinyl group, a 10-phenothiazinyl group, a 1- Oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-oxazolyl group, 2- Thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2- Methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-tert-butyl Indolyl group, 2-methyl-3-indolyl group, 4-methyl-1-indolyl group, Indolyl group, 2-tert-butyl-1-indolyl group, 4-tert-butyl-1-indolyl group, 2-tert- .

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 Propyl group, sec-butyl group, isobutyl group, tert-butyl group and the like.

Specific examples of the C _{5 -30} alkyl group of R ¹ to R ²⁴ include a cyclohexyl group, a cycloheptyl group and a cyclooctyl group.

Specific examples of the thio group of C _{1 -30} as the group corresponding to the above "substitution" include methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, tri (isopropyl) thio, tri (isobutyl) alkylthio, tri (tert - butyl) thio, tri (2-butyl) thio, phenylthio, naphthylthio, biphenyl thio, (3-methylphenyl) thio, (4-methyl-naphthyl) thio, (2-methyl-by Phenyl) thio group and the like.

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 - Tri (3-methylphenyl) silyl, tri (4-methylnaphthyl) silyl, triphenylsilyl, tri (Isopropyl) silyl, naphthyl (isopropyl) silyl, or phenyl or naphthyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, Biphenyl (isopropyl) silyl group and the like.

In order to solve the problems of the conventional arylamine compounds, the present invention is applied to an organic electroluminescent device using a hole transporting material, a hole injecting material, a light emitting layer material, a host material of a light emitting layer, an electron transporting material, And an aromatic amine compound exhibiting excellent quantum efficiency was prepared.

In the following, the formulas 1 to 22 of the aromatic amine compounds of the present invention are shown in Table 1, but the present invention is not limited to the compounds represented by these 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 electroluminescent device according to the present invention will now be described with reference to the accompanying drawings. 1 is a schematic view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device including the aromatic amine compound represented by the structural formulas 1 to 3 may be realized in various structures.

Referring to FIG. 1, one embodiment of the present invention includes 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. 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 layer may be a light emitting layer (130).

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

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

 According to another embodiment of the present invention, the organic material layer 130 may be an electron transport layer.

According to another embodiment of the present invention, the organic material layer 130 may be an electron injection layer.

Referring to FIG. 2, another embodiment of the present invention includes a plasma display panel including a first electrode 110; A second electrode (150); And a light emitting layer 135 between the first electrode 110 and the second electrode 150. The organic electroluminescent device includes a host and a dopant, An aromatic amine compound according to the present invention can be provided.

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

According to another embodiment of the present invention, an electron transport layer 137 may be additionally provided 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 additionally provided 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 cathode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of 4 eV or more 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 the anode material of the organic electroluminescent 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 may 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 hundreds? / Mm or less. The thickness of the electrode is 10 nm to 1 탆, more preferably 10 to 400 nm. Such an electrode can be manufactured by forming the electrode material into a thin film by a vapor deposition method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) or a sputtering method.

When the aromatic amine compound for an organic electroluminescence device of the present invention is used as at least one member selected from the group consisting of a hole transporting material, a hole injecting material, a light emitting layer material, a host material of a light emitting layer, an electron transporting material, The hole transporting material, the hole injecting material, the light emitting layer material, the host material of the light emitting layer, the electron transporting material, and the electron injecting material, which are not used in the aromatic amine compound for the organic electroluminescence device of the present invention, , A light emitting layer material, a host material of a light emitting layer, an electron transporting material, and an electron injecting material may be used.

Hereinafter, the hole transporting material, the hole injecting material, the light emitting layer material, the host material of the light emitting layer, the electron transporting material, and the electron injecting material will be described.

The hole transporting layer or the hole injecting layer of the present invention can be used as a hole transporting material and a hole injecting material in a material commonly used as a hole transporting material in a photoconductive material and a known material used for forming a hole transporting layer or a hole injecting layer . ≪ / RTI > For example, N, N-dicarbazolyl-3,5-benzene (mCP), poly (3,4- ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS) (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'- diaminobiphenyl (TPD) N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N'N'N'N'- Porphyrin compound derivatives such as tetraphenyl-4,4'-diaminobiphenyl, copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin and the like, aromatic tertiary (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives such as nonmetal phthalocyanine and copper phthalocyanine, Amine May be a conductor, enamine stilbene derivatives, derivatives of aromatic tertiary amines and styrylamine compounds, polysilane and the like.

An electron transport layer of the present invention, a known electron transport material, for example, diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq 3, 2,5- diaryl silole derivatives (PyPySPyPy), perfluoro rineyi suited compound (PF -6P), octasubstituted cyclooctatetraene compounds (COTs).

In the organic electroluminescent device of the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be formed of a single layer containing at least one kind of the above-mentioned compounds, And the like.

The light emitting layer of the organic electroluminescent device of the present invention may include known light emitting materials such as a phosphorescent fluorescent material, a fluorescent whitening agent, 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 A dyestuff, a dyestuff, a xanthene dye, a carbostyryl dye, a perylene dye, an oxazine compound, a stilbene derivative, a spiro compound, an oxadiazole compound 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 Structural Formulas 1 to 3 according to the present invention can be formed by a vacuum deposition method, there is an advantage that a thin film forming process is simple and a homogeneous thin film having almost no pinhole can be easily obtained.

Hereinafter, an aromatic amine compound according to the present invention and a method of manufacturing an organic electroluminescent device including the same 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 prepared using this compound. The following Preparation Examples and Examples are intended to illustrate the present invention specifically and should not be construed as limiting the invention.

Manufacturing example  One. Chemicals  Synthesis of 1

Synthesis of Intermediate 1

 To a solution of 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 tert-butoxide (17.7 g, 184 mmol ) Was dissolved in anhydrous toluene. Tri-t-butylphosphine (1 M toluene solution, 9.2 mL) was slowly added to the reaction solution under a nitrogen atmosphere, followed by reflux stirring 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 resultant product 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

(1.2 g, 3.81 mmol), 3-biphenylboronic acid (1.81 g, 9.12 mmol), tetrakis (triphenylphosphine) palladium (0) (0.26 g, 0.23 mmol) and THF (100 mL) were charged into a two-necked flask and bubbled with nitrogen for 30 minutes. 30 mL (3.16 g) of the degassed potassium carbonate aqueous solution was added thereto, followed by reflux stirring for 24 hours. The reaction solution was extracted with dichloromethane and distilled water, and the organic layer was separated and dried with magnesium sulfate. After the solvent was removed, the residue was subjected to column chromatography 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 ~ 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 551 [(M + H) < ⁺ & gt ^; ].

Manufacturing example  2. Chemicals  Synthesis of 2

 (1.0 g, 3.17 mmol) and 3-biphenylboronic acid were reacted with 3- (9H-carbazol-9-yl) phenylboronic acid (2.19 g, 7.61 mmol), Compound 2 was synthesized in the same manner as Compound 1 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

MS (FAB) m / z 729 [(M + H) < ⁺ & gt ^; ].

Manufacturing example  3. Synthesis of Compound 3

 4-amine (1.5 g, 4.76 mmol) and 3-biphenylboronic acid were reacted with dibenzofuran-2-ylboronic acid (2.42 g, 11.4 mmol ), Compound 3 was synthesized in the same manner as 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

MS (FAB) m / z 579 [(M + H) < ⁺ & gt ^; ].

Manufacturing example  4. Synthesis of Compound 4

Synthesis of intermediate 2

To a solution of 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 tert- mmol) were dissolved in anhydrous toluene. Tri-t-butylphosphine (1 M toluene solution, 2.8 mL) was slowly added to the reaction solution under a nitrogen atmosphere, followed by reflux stirring 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 resultant product 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

(2.0 g, 10.5 mmol), tetrakis (triphenylphosphine) palladium (0) (0.30 g, 0.26 mmol) and THF (45 mL) were added to a solution of intermediate 2 (1.5 g, 4.37 mmol) Were charged into a two-necked flask and subjected to nitrogen bubbling for 30 minutes. 15 mL (3.62 g) of degassed potassium carbonate aqueous solution was added thereto, followed by reflux stirring for 24 hours. The reaction solution was extracted with dichloromethane and distilled water, and the organic layer was separated and dried with magnesium sulfate. After removing the solvent, the mixture was subjected to column chromatography 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) < ⁺ & gt ^; ].

Manufacturing example  5. Chemicals  Synthesis of 5

Synthesis of intermediate 3

Palladium acetate (0.12 g, 0.54 mmol) and sodium tert-butoxide (3.10 g, 32.2 mmol) in anhydrous tetrahydrofuran (10 mL) ) Was dissolved in anhydrous toluene. Tri-t-butylphosphine (1 M toluene solution, 2.7 mL) was slowly added to the reaction solution under a nitrogen atmosphere, followed by reflux stirring 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 resultant product 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

3-Biphenylboronic acid (2.57 g, 13.0 mmol), tetrakis (triphenylphosphine) palladium (0) (0.30 g, 0.26 mmol) and THF (100 mL) Were charged into a two-necked flask and subjected to nitrogen bubbling for 30 minutes. 30 mL (3.59 g) of degassed potassium carbonate aqueous solution was added, and the mixture was refluxed and stirred for 24 hours. The reaction solution was extracted with dichloromethane and distilled water, and the organic layer was separated and dried with magnesium sulfate. After the solvent was removed, the residue was subjected to column chromatography 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) < ⁺ & gt ^; ].

Manufacturing example  6. Synthesis of Compound 21

Synthesis of Intermediate 4

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 nitrogen atmosphere, followed by reflux stirring 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 resultant product 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

A solution of intermediate 4 (2.0 g, 4.4 mmol), phenylboronic acid (4.8 g, 39.6 mmol), tetrakis (triphenylphosphine) palladium (0) (0.91 g, 0.79 mmol) and THF The flask was charged with nitrogen bubbling for 30 minutes. 50 mL of an aqueous potassium carbonate solution degassed (10.9 g of potassium carbonate) was added thereto, followed by reflux stirring for 24 hours. The reaction solution was extracted with dichloromethane and distilled water, and the organic layer was separated and dried with magnesium sulfate. After the solvent was removed, the residue was subjected to column chromatography 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) < ⁺ & gt ^; ].

Example  One

Compound 1 synthesized in the present invention was applied as a light emitting host material of a blue phosphorescent device to produce a blue phosphorescent device. 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- ] -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.

The fabrication of the device was performed in the following manner.

The ITO substrate was cleaned with pure water and isopropyl alcohol for 30 minutes by ultrasonic wave, and the ITO substrate was surface-treated with ultraviolet rays of short wavelength and vacuum was deposited on the ITO substrate under a pressure of ¹ × 10 ^-6 torr. DNTPD, NPB, mCP and TSPO1 as common layer materials were deposited at a rate of 0.1 nm / s to form a film corresponding to each thickness. Compound 1, which is a blue phosphorescent host material, was vacuum deposited at the same time as FIrpic, a phosphorescent dopant material. The deposition rates were 0.1 nm / s for mCP and 0.015 nm / s for FIrpic. LiF was formed to a thickness of 1 nm at a rate of 0.01 nm / s, and Al was formed to 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 wetting agent and a glass cover glass.

The above compound 1 was applied as a light emitting host material of a blue phosphorescent device and quantum efficiency of 14.0%, current efficiency of 24.3 cd / A, power efficiency of 16.9 lm / W at a voltage of 5 V and x = 0.15 and y = 0.31 And showed excellent blue phosphorescence characteristics.

Example  2

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

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

The above compound 2 was applied as a light emitting host material of a blue phosphorescent device and quantum efficiency of 15.6%, current efficiency of 27.5 cd / A, power efficiency of 19.1 lm / W at a voltage of 5 V and x = 0.15 and y = 0.32 And showed excellent blue phosphorescence characteristics.

Example  3

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

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

The above compound 3 was applied as a light emitting host material of a blue phosphorescent device and quantum efficiency of 16.1%, current efficiency of 27.8 cd / A, power efficiency of 19.3 lm / W at a voltage of 5 V and x = 0.14 and y = 0.31 based on CIE 1931 color coordinates And showed excellent blue phosphorescence characteristics.

Example  4

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

The compound 1 and the compound 21 were applied to the light emitting layer host and the electron transport layer material of the blue phosphorescent device, respectively, and a quantum efficiency of 18.1%, a current efficiency of 35.9 cd / A, a power efficiency of 22.7 lm / W and a CIE 1931 color coordinate x = 0.16 and y = 0.38, indicating excellent blue phosphorescence characteristics.

Comparative Example  One

In order to compare the characteristics of the compounds synthesized in the present invention, mCP was applied as a blue phosphorescent host material to fabricate an organic electroluminescent device.

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

The above mCP and TSPO1 were applied to the light emitting host of the blue phosphorescent device and the electron transport layer material, respectively. The quantum efficiency was 13.8%, the current efficiency was 25.2 cd / A, the power efficiency was 17.5 lm / 0.16 and y = 0.34, respectively.

The quantum efficiencies of Examples 1 to 4 and Comparative Example 1 are described in Forrest's paper (G. Gu and SR Forrest, IEEE Journal of Selected Topics in Quantum Electronics, Vol. 4, No. 1, January / February 1998, p. ).

Referring to FIG. 3, the absorption spectrum, the solution (THF) emission spectrum, the solid emission spectrum and the low temperature emission spectrum of Compound 2 are shown. As shown in FIG. 3, the maximum fluorescence emission wavelength of the compound 2 was 421 nm in the solution, and the phosphorescent emission wavelength was 449 nm in the low temperature emission spectrum, and the triplet energy was 2.76 eV. Thus, it can be used as a blue or green phosphorescent host material.

Claims (19)

The aromatic amine compound for an organic electroluminescence device according to any one of the following compounds 1 to 3.
[Compound 1]

[Compound 2]

[Compound 3]

delete delete delete delete delete delete delete A first electrode; A second electrode; And an organic material layer between the first electrode and the second electrode, the organic electroluminescent device comprising:
Wherein the organic material layer comprises the aromatic amine compound according to claim 1. 10. The method of claim 9,
Wherein the organic material layer is a light emitting layer. 10. The method of claim 9,
Wherein the organic material layer is a hole transport layer. 10. The method of claim 9,
Wherein the organic material layer is a hole injection layer. 10. The method of claim 9,
Wherein the organic material layer is an electron transporting layer. 10. The method of claim 9,
Wherein the organic material layer is an 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 comprises a host and a dopant,
The organic electroluminescent device according to claim 1, wherein the host comprises an aromatic amine compound according to claim 1. delete delete delete delete

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