KR20140018789A - Compound for organic electroluminescent device and organic electroluminescent device including the same - Google Patents

Abstract

Disclosed are a compound for an organic electroluminescent device and an organic electroluminescent device including the same. The present invention can improve thermal stability and luminous efficiency of the organic electroluminescent device including the compound for an organic electroluminescent device. The present invention can improve luminous efficiency of the organic electroluminescent device by enhancing triplet energy of phosphorescent luminous material using the compound of the present invention as a hole transportation material.

Description

Compound for organic electroluminescent device and organic electroluminescent device comprising same {COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME}

The present invention relates to a compound for an organic light emitting device and an organic light emitting device comprising the same, and more particularly to a compound for an organic light emitting device having a high luminous efficiency and low driving voltage and an organic light emitting device comprising the same. .

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 type organic electroluminescence 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.

Since the thin film formed by vacuum evaporation is not sufficiently thermally and electrically stable, the hole transport material of the organic light emitting device is known until now, the crystallization of the thin film is promoted by the heat generation during driving of the device, and the film quality is ultimately changed. The luminous efficiency of the device is lowered. Furthermore, there is a problem that a non-light emitting portion called a dark spot is generated and increased, and a voltage is increased at the time of constant current driving, and eventually the device is broken.

In addition, an organic electroluminescent device using a phosphorescent light emitting material due to low triplet energy has a disadvantage in that it can not confine the triplet anti-exciton generated in the light emitting material of the light emitting layer.

An object of the present invention is to provide a compound for an organic light emitting device having high thermal stability and high hole transporting properties of triplet energy.

In addition, another object of the present invention is to improve the thermal stability and luminous efficiency of the organic electroluminescent device using the compound for an organic electroluminescent device of the present invention, by using the compound as a hole transport layer material, triplet of a phosphorescent light emitting material Increasing the energy to improve the efficiency of the organic light emitting device.

According to one aspect of the present invention for achieving the above object there is provided a compound for an organic light emitting device represented by any one of the following structural formulas 1 to 6.

In the above Structural Formulas 1 to 6,

R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,

m is 0 or 1,

n is 0 or 1,

m + n = 1,

또는

이거나, 또는 R³ 내지 R¹⁴ 중 적어도 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로아릴기를 형성할 수 있고,R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,A ¹ and A ² may be the same or different from each other, and A ¹ and A ² each independently represents a valence bond or

ego,

R ¹⁸ and R ¹⁹ may be the same as or different from each other, R ¹⁸ and R ¹⁹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,

a1 is 0 or 1,

a2 is 0 or 1;

According to an embodiment of the present invention, preferably,

The organic electroluminescent device compound is represented by any one of the following structural formulas 7 to 9,

In the above Structural Formulas 7 to 9,

R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,

m is 0 or 1,

n is 0 or 1,

m + n = 1,

또는

이거나, 또는 R³ 내지 R¹⁴ 중 적어도 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로아릴기를 형성할 수 있고,R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,A < ^{1 >} is a valence bond or

ego,

R ¹⁸ and R ¹⁹ may be the same as or different from each other, R ¹⁸ and R ¹⁹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,

a1 may be 0 or 1;

According to another embodiment of the present invention, preferably,

The compound for an organic electroluminescence device is represented by the following structural formula 10,

 [Structural Formula 10]

In the above formula 1,

R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,

m is 0 or 1,

n is 0 or 1,

m + n = 1,

또는

이거나, 또는 R³ 내지 R¹⁴ 중 적어도 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로아릴기를 형성할 수 있고,R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 To C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween. Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted It may be a substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

According to another embodiment of the present invention, preferably,

,

,

,

, 치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이거나, 또는 R¹은 R¹이 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로아릴기를 형성할 수 있고, R ¹ and R ² may be the same or different from each other, and R ¹ and R ² are each independently a hydrogen atom,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or R ¹ is adjacent to a carbon atom to which R ¹ is bonded A substituted or unsubstituted fused C3 to C30 cycloalkyl group further substituted with a carbon atom, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or To form an unsubstituted fused C1 to C30 heteroaryl group,

또는

이고,Y ¹ and Y ² may be the same or different from each other, Y ¹ and Y ² are each independently an oxygen atom, a sulfur atom,

or

ego,

Ar ⁷ Is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

R ²⁹ and R ³⁰ may be the same as or different from each other, R ²⁹ and R ³⁰ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

Ar ³ to Ar ⁶ may be the same as or different from each other, Ar ³ to Ar ⁶ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ³ and Ar ⁴ , and Ar ⁵ and Ar ⁶ are each bonded to each other Or a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group together with a nitrogen atom of N, or at least one of Ar ³ to Ar ⁶ is a nitrogen to which any one is bonded Further bonding with a carbon atom at the β-position of the atom forms a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group May,

R ²⁰ to R ²⁸ may be the same as or different from each other, R ²⁰ to R ²⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

q can be 0 or 1.

According to another embodiment of the present invention, preferably,

Ar ³ to Ar ⁶ may be the same as or different from each other, Ar ³ to Ar ⁶ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ³ to Ar ⁶ is a β of the nitrogen atom to which one is bonded It may further combine with a carbon atom at the position to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.

According to another embodiment of the present invention, preferably,

Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to It may be a C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

 According to another aspect of the present invention, the compound for an organic light emitting device may be any one selected from compounds 1 to 48 represented by the following formula.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound for an organic electroluminescent device.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode, The organic electroluminescent device may further include at least one organic compound layer including the organic electroluminescent compound.

The singular or plural organic layers may include a light emitting layer.

The plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer, and a hole injecting layer.

The light emitting layer may include a host and a dopant.

According to one embodiment of the present invention, a compound in which one or two diarylamines are substituted in the ortho or meta position of a phenyl group in a carbazole derivative having a phenyl group bonded thereto, and the organic electroluminescent device It is included in the organic layer of, and by using the same to increase the triplet energy of the phosphorescent light emitting material of the organic light emitting device there is an effect that can improve the thermal stability and luminous efficiency.

1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

The invention is capable of various modifications and may have various embodiments, and particular embodiments are exemplified and will be described in detail in the detailed description. It is to be understood, however, that the invention is not to be limited to the specific 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 >

Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms "comprise" or "having" 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 used herein, "atomic bond" means a single bond, a double bond or a triple bond, unless otherwise defined.

As used herein, unless otherwise defined, "substituent" means that at least one hydrogen in the substituent or compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C30 silyl group, An alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C1 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, It means that it has been replaced by anger.

A C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 aryl group, a C1 to C30 aryl group, a C1 to C30 aryl group, An alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group may be fused to form a ring.

As used herein, unless otherwise defined, it is meant that one functional group contains 1 to 4 heteroatoms selected from the group consisting of N, O, S, and P, and the remainder is carbon.

In the present specification, the term "combination thereof" means that two or more substituents are bonded to each other via a linking group or two or more substituents are condensed and bonded.

As used herein, "hydrogen" means monohydrogen, double hydrogen, or tritium, unless otherwise defined.

As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group.

The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

The alkyl group may be an "unsaturated alkyl group" comprising at least one double bond or triple bond.

"Alkynylene group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynylene group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding. The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.

The alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group, a C1 to C10 alkyl group or a C1 to C6 alkyl group.

For example, the C1 to C4 alkyl groups may have 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.

The "amine group" includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.

"Cycloalkyl group" includes monocyclic or fused-ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

"Heterocycloalkyl group" means that the cycloalkyl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the remainder is carbon. When the heterocycloalkyl group is a fused ring, it may contain 1 to 4 heteroatoms in each ring.

"An aromatic group" means a functional group in which all elements of a functional group in the form of a ring have a p-orbital, and these p-orbital forms a conjugation. Specific examples thereof include an aryl group and a heteroaryl group.

An "aryl group" includes a monocyclic or fused ring polycyclic (i. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

"Heteroaryl group" means that the aryl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 4 heteroatoms in each ring.

In the aryl group and the heteroaryl group, the number of atoms in the ring is the sum of carbon number and non-carbon atom number.

When used in combination, such as "alkylaryl" or "arylalkyl group ", the terms alkyl and aryl of each of the above have the meanings and contents indicated above.

The term "arylalkyl group " means an aryl substituted alkyl radical, such as benzyl, and is included in the alkyl group.

The term "alkylaryl group " means an alkyl substituted aryl radical and is included in the aryl group.

The "carbon atom at the β-position" of an atom refers to the carbon atom adjacent to another atom to which that atom is bonded. For example, a carbon atom at the β-position of a nitrogen atom is a carbon atom indicated by an arrow in the following structural formula.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT Hereinafter, embodiments of the present invention will be described with reference to the accompanying drawings. Referring to the accompanying drawings, the same or corresponding components are denoted by the same reference numerals, .

According to one aspect of the present invention, there is provided an organic electroluminescent device compound represented by any one of the following Structural Formulas 1 to 6.

In the above Structural Formulas 1 to 6,

R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,

m is 0 or 1,

n is 0 or 1,

m + n = 1,

또는

이거나, 또는 R³ 내지 R¹⁴ 중 적어도 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로아릴기를 형성할 수 있고,R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,A ¹ and A ² may be the same or different from each other, and A ¹ and A ² each independently represents a valence bond or

ego,

R ¹⁸ and R ¹⁹ may be the same as or different from each other, R ¹⁸ and R ¹⁹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,

a1 is 0 or 1,

a2 is 0 or 1;

According to an embodiment of the present invention, preferably,

The organic electroluminescent device compound is represented by any one of the following structural formulas 7 to 9,

In the above Structural Formulas 7 to 9,

R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,

m is 0 or 1,

n is 0 or 1,

m + n = 1,

또는

이거나, 또는 R³ 내지 R¹⁴ 중 적어도 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로아릴기를 형성할 수 있고,R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,A < ^{1 >} is a valence bond or

ego,

R ¹⁸ and R ¹⁹ may be the same as or different from each other, R ¹⁸ and R ¹⁹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,

a1 may be 0 or 1;

According to another embodiment of the present invention, preferably,

The compound for an organic electroluminescence device is represented by the following structural formula 10,

 [Structural Formula 10]

In the above formula 1,

R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,

m is 0 or 1,

n is 0 or 1,

m + n = 1,

또는

이거나, 또는 R³ 내지 R¹⁴ 중 적어도 어느 하나는 그 어느 하나가 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로아릴기를 형성할 수 있고,R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 To C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween. Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,

R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted It may be a substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

According to another embodiment of the present invention, preferably,

,

,

,

, 치환 또는 비치환된 C1 내지 C30의 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이거나, 또는 R¹은 R¹이 결합된 탄소원자의 이웃한 탄소원자와 추가로 결합하여 치환 또는 비치환된 융합된 C3 내지 C30 시클로알킬기, 치환 또는 비치환된 융합된 C1 내지 C30 헤테로시클로알킬기, 치환 또는 비치환된 융합된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 융합된 C1 내지 C30 헤테로아릴기를 형성할 수 있고, R ¹ and R ² may be the same or different from each other, and R ¹ and R ² are each independently a hydrogen atom,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or R ¹ is adjacent to a carbon atom to which R ¹ is bonded A substituted or unsubstituted fused C3 to C30 cycloalkyl group further substituted with a carbon atom, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or To form an unsubstituted fused C1 to C30 heteroaryl group,

또는

이고,Y ¹ and Y ² may be the same or different from each other, Y ¹ and Y ² are each independently an oxygen atom, a sulfur atom,

or

ego,

Ar ⁷ Is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,

R ²⁹ and R ³⁰ may be the same as or different from each other, R ²⁹ and R ³⁰ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

Ar ³ to Ar ⁶ may be the same as or different from each other, Ar ³ to Ar ⁶ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ³ and Ar ⁴ , and Ar ⁵ and Ar ⁶ are each bonded to each other Or a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group together with a nitrogen atom of N, or at least one of Ar ³ to Ar ⁶ is a nitrogen to which any one is bonded Further bonding with a carbon atom at the β-position of the atom forms a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group May,

R ²⁰ to R ²⁸ may be the same as or different from each other, R ²⁰ to R ²⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

q can be 0 or 1.

According to another embodiment of the present invention, preferably,

Ar ³ to Ar ⁶ may be the same as or different from each other, Ar ³ to Ar ⁶ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ³ to Ar ⁶ is a β of the nitrogen atom to which one is bonded It may further combine with a carbon atom at the position to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group.

According to another embodiment of the present invention, preferably,

Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to It may be a C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

Examples of the substituted or unsubstituted C6 to C30 aryl group include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthalenyl group, a substituted or unsubstituted naphthalenyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted furanyl group, Lt; / RTI >

Examples of the substituted or unsubstituted C1 to C30 heteroaryl group include a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted thiophenyl group , A substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo [1,2-a] pyridinyl group, a substituted or unsubstituted A substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzoyl group, Substituted or unsubstituted imidazolyl groups, substituted or unsubstituted thiazolyl groups, substituted or unsubstituted tetrazolyl groups, substituted or unsubstituted oxadiazolyl groups, substituted or unsubstituted oxatriazolyl groups, However, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyridinyl group, Or a substituted or unsubstituted phenanthrolinyl group, preferably a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted aryidinyl group, a substituted or unsubstituted pyrazolinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, A substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzothiazolyl group, , A substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.

According to another aspect of the present invention, there may be provided a compound for an organic electroluminescent device which is any one selected from compounds 1 to 48 represented by the following structural formula.

Referring to FIGS. 1 and 2, an organic electroluminescent device 1 including the compound for an organic electroluminescent device according to the present invention can be provided according to an embodiment of the present invention.

According to another embodiment of the present invention, the organic electroluminescent device includes a first electrode 110; A second electrode (150); And one or more organic layers 130 between the first and second electrodes and at least one organic layer selected from the single or plurality of organic layers 130 include the compound for an organic light emitting device according to the present invention can do.

Here, the single or plural organic layers 130 may include a light emitting layer 134.

The plurality of organic layers 130 may include a light emitting layer 134 and the plurality of organic layers may include an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, Transporting layer 136 and hole-injecting layer 137 may be further included.

The light emitting layer 134 may include a host and a dopant.

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 compound for an organic electroluminescence device of the present invention is used for the purpose of the present invention, the known hole transporting material, hole injecting material, light emitting layer material, host material of the light emitting layer, electron transporting material, Or may be used in combination with the organic electroluminescent device compound of the present invention selectively.

N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS), N, N'- (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, An aminostilbene derivative, a derivative of an aromatic tertiary amine and a styrylamine compound, and polysilane.

The diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq 3, 2,5- diaryl silole derivatives (PyPySPyPy), perfluoro rineyi suited compound (PF-6P), Octasubstituted cyclooctatetraene compound (COTs) as an electron transport material .

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.

Examples of the light emitting material include 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 There may be mentioned a colorant, a xanthene colorant, a carbostyryl colorant, a perylene colorant, an oxazine compound, a stilbene derivative, a spiro compound, and an oxadiazole compound.

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.

The compound for an organic electroluminescence device according to the present invention can be formed by a vacuum deposition method, so that it is advantageous that a thin film forming process is simple and a homogeneous thin film having almost no pinhole can be easily obtained.

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

[Example]

Manufacturing example  1.Intermediate (1) 3,5- Dibromobiphenyl  synthesis

In a 250 ml round bottom three necked flask under nitrogen atmosphere, 6 g of 1,3-dibromo-5-iodobenzene, 2.2 g of phenylboronic acid, 1.5 g of tetrakis triphenylphosphine palladium (0), 4.6 g of potassium carbonate, toluene 60 ml and 20 ml of methanol were added and stirred at 65 ° C. for 4 hours. The reaction solution is cooled, extracted with dichloromethane and water, and the extracted solution is concentrated. The solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane, and the solution was concentrated to obtain 6.08 g of 3,5-dibromobiphenyl. (71% yield)

1 H NMR (CDCl ₃ , 600 MHz) δ 7.64 (s, 2H), 7.62 (s, 1H), 7.52-7.50 (d, 2H), 7.46-7.43 (dd, 2H), 7.40-7.38 (dd, 1H)

Manufacturing example  2. Intermediate (2) 2,6- Dibromobiphenyl  synthesis

Except for using 1,3-dibromo-5-iodobenzene in Preparation Example 1, except that 6g of 1,3-dibromo-2-iodobenzene was used, 2,6-dibro 4.2 g of mobiphenyl was obtained. (70% yield)

_{1H NMR (CDCl 3, 600MHz)} δ 7.64-7.62 (d, 2H), 7.47-7.44 (dd, 2H), 7.43-7.42 (d, 1H), 7.21-7.20 (dd, 2H), 7.08-7.04 (dd , 1H)

Manufacturing example  3. Intermediate (3) 3- (3,5- Dibromophenyl ) -9- Phenyl -9H- Carbazole  synthesis

3- (3,5-dibromophenyl) -9-phenyl-9H-carba in the same manner as in Production Example 1, except that 4.7 g of N-phenylcarbazole-3-boronic acid was added instead of phenylboronic acid. 3.5 g of sol was obtained. (Yield: 56%)

1 H NMR (CDCl ₃ , 600 MHz) δ 8.28 (s, 1H), 8.20-8.18 (d, 1H), 7.78-7.77 (s, 2H), 7.63-7.61 (m, 3H), 7.58-7.55 (m, 3H ), 7.51-7.48 (dd, 1H), 7.45-7.40 (m, 3H), 7.34-7.31 (dd, 1H)

Manufacturing example  4. Intermediate (4) 3- (2,6- Dibromophenyl ) -9- Phenyl -9H- Carbazole  synthesis

Except for adding 4.7 g of N-phenylcarbazole-3-boronic acid instead of phenylboronic acid in Preparation Example 2, 3- (2,6-dibromophenyl) -9-phenyl-9H-carba 3.6 g of sol were obtained. (Yield: 56%)

_{1H NMR (CDCl 3, 600MHz)} δ 8.13-8.12 (d, 1H), 7.98 (s, 1H), 7.68-7.66 (d, 2H), 7.63-7.60 (m, 4H), 7.49-7.47 (m, 2H ), 7.42-7.40 (m, 2H), 7.33-7.23 (m, 2H), 7.10-7.071 (dd,

Manufacturing example  5. Intermediate (5) N, N- Diphenyl -3- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane -2 days) Benzeneamine  synthesis

In a round bottom three-necked flask under nitrogen atmosphere, 10 g of 3-bromo-N, N-diphenylbenzeneamine, 11.7 g of bispinolacholate diboron, 9.1 g of potassium acetate, [1,1'-bis (diphenylphosphinoferrocene) 0.76 g of dichloropalladium (II) and 100 ml of DMSO were added and stirred at 80 ° C for 10 hours. The reaction solution is cooled, extracted with dichloromethane and water, and the extracted solution is concentrated. N, N-diphenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 was concentrated by column chromatography using dichloromethane and n-hexane mixed solvent. -Yl) benzeneamine 3.9g was obtained. (Yield: 38%)

_{1H NMR (CDCl 3, 600MHz)} δ 7.57 (s, 1H), 7.49-7.48 (d, 1H), 7.26-7.24 (dd, 1H), 7.22-7.20 (m, 4H), 7.17 (d, 1H), 7.07-7.03 (d 4H), 6.98-6.95 (dd, 2H), 1.31-1.28 (m, 12H)

Manufacturing example  6. Intermediate (6) 3- Bromo -4- methyl -N, N-di-p- Of tolylbenzeneamine  synthesis

In a round bottom three-necked flask under nitrogen atmosphere, 20 g of 2-bromo-4-iodine toluene, 12.6 g of diphenylamine, 19.4 g of t-butoxy sodium, 0.5 g of tris (dibenzylideneacetone) dipalladium (0) , 0.3 g of triphenylphosphine and 200 ml of toluene are added to a round bottom flask, and the mixture is stirred while maintaining the temperature at 80 ° C. The reactor-wise solution is extracted with dichloromethane and water and concentrated. The solution, which was subjected to column chromatography with dichloromethane and n-hexane, was concentrated to give 17 g of 3-bromo-4-methyl-N, N-diphenylbenzeneamine compound. (Yield: 74%)

Manufacturing example  7. Intermediate (7) 4- methyl -3- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane -2-yl) -N, N-di-p- Of tolylbenzeneamine  synthesis

In the same manner as in Preparation Example 5, 2-bromo-4-iodine toluene was added instead of 3-bromo-N, N-diphenylbenzeneamine prepared in Preparation Example 6 to 4-methyl-3- (4,4, 10 g of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -N, N-di-p-tolylbenzeneamine were obtained. (Yield: 52%)

_{1H NMR (CDCl 3, 600MHz)} δ 7.79-7.78 (d, 1H), 7.12-7.16 (dd, 1H), 7.06-6.94 (m, 9H), 2.31-2.20 (m, 9H)

Manufacturing example  8. Intermediate (8) 3,5- Vis ( Diphenylamine )-One- Of bromobenzene  synthesis

5 g of 3,5-bis (diphenylamine) -1-bromobenzene using 9 g of 1,3,5-tribromobenzene and 8 g of diphenylamine in the same manner as in Preparation Example 6 (yield 35% )

_{1H NMR (CDCl 3, 600MHz)} δ 7.24-7.21 (t, 8H), 7.08-7.06 (d, 8H), 7.02-7.00 (t, 4H), 6.75-6.74 (d, 2H), 6.71-6.70 (d , 1H)

Manufacturing example  9. Intermediate (9) 3,5- Vis ( Diphenylamine )-One- Of pinacolyte boron benzene  synthesis

5 g of 3,5-bis (diphenylamine) -1-bromobenzene (yield 35%) using 10 g of 3,5-bis (diphenylamine) -1-bromobenzene in the same manner as in Preparation Example 5 Got.

_{1H NMR (CDCl 3, 600MHz)} δ 7.20-7.19 (d, 2H), 7.19-7.16 (t, 8H), 7.02-7.01 (d, 8H), 6.94-6.91 (m, 5H), 1.26 (s, 12H )

Manufacturing example  10. Intermediates (10) N, N, N ' - Triphenylbenzene -1,4- Diamine  synthesis

To a 250 ml three-neck round bottom flask under a nitrogen atmosphere were added 10 g of 4-bromo-N, N-diphenylbenzeneamine, 4.4 g of aniline, 6 g of t-butoxysodium, 0.8 g of tris (dibenzylideneacetone) dipalladium g, 0.4 g of tris (t-butyl) phosphine and 100 ml of toluene, and the mixture was stirred at 90 ° C for 12 hours. The reaction solution is extracted with dichloromethane and concentrated. Column chromatography with dichloromethane and n-hexane was concentrated to give 6.6 g of N, N, N'-triphenylbenzene-1,4-diamine. (Yield: 65%)

Manufacturing example  11.Intermediate (11) N- (3- Bromophenyl ) -N, N ' , N- Triphenylbenzene -1,4- Diamine  synthesis

In the same manner as in Preparation Example 10, 6.6 g of N, N, N'-triphenylbenzene-1,4-diamine prepared in Preparation Example 10 and 10 g of 3-bromo-iodinebenzene were added thereto to react with N- (3-bromine. 4.6 g of parent) -N, N ', N-triphenylbenzene-1,4-diamine was obtained. (Yield 50%)

Manufacturing example  12. Intermediate (12) N, N, N ' - Triphenyl - N ' -(3- (4,4,5,5- Tetramethyl -1,3,2-dioxaborolan-2-yl)- Phenyl ) Benzene-1,4- Diamine  synthesis

In the same manner as in Preparation Example 5, 4.6 g of N- (3-bromo) -N, N ', N'-triphenylbenzene-1,4-diamine prepared in Preparation Example 11 was added and reacted to form N, N, N. '-Triphenyl-N'-(3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -phenyl) benzene-1,4-diamine 2.2 g Got. (Yield 50%)

Manufacturing example  13. Intermediate (13) 2- Methoxycarbonyl -3 ', 5'- Dibromobiphenyl  synthesis

In the same manner as in Preparation Example 1, 10 g of 2- (methoxycarbonyl) phenylboronic acid and 19 g of 1,3,5-tribromobenzene were added thereto to react with 2-methoxycarbonyl-3 ', 5'-dibro. 11 g of mobiphenyl was obtained. (Yield: 54%)

Manufacturing example  14. Intermediate (14) 2- (3 ', 5,- Dibromobiphenyl Synthesis of 2-yl) -propan-2-ol

Intermediate (13) synthesized in Preparation Example 13 was dissolved in THF, 40 ml of methylmagnesium bromide diluted with 3M in THF was added dropwise, and the mixture was stirred at 60 占 폚 for 12 hours. The cooled reaction solution was extracted with ethyl acetate and water, subjected to column chromatography with dimethyl chloride and n-hexane and concentrated to 2- (3 ', 5, -dibromobiphenyl-2-yl) -propan-2-ol 11 g was obtained. (Yield: 82%)

Manufacturing example  15. Intermediate (15) 1,3- Dibromo -9,9-dimethyl-9H- Fluorene  synthesis

The intermediate (14) synthesized in Preparation Example 14 was dissolved in 200 ml of acetic acid and 300 ml of phosphoric acid, and the mixture was stirred at 120 占 폚 for 12 hours. The cooled reaction solution was washed with water, extracted with ethyl acetate, subjected to column chromatography with dimethyl chloride and n-hexane and concentrated to give 5 g of 1,3-dibromo-9,9-dimethyl-9H-fluorene. (Yield: 44%)

Manufacturing example  16. Intermediate (16) N- (biphenyl-4-yl) -N- (3- Bromophenyl ) -Biphenyl-4- Amine  synthesis

In the same manner as in Preparation Example 11, 5 g of 4,4'-bisbiphenylamine and 4.5 g of 3-bromo-iodinebenzene were added thereto, and reacted with N- (biphenyl-4-yl) -N- (3-bromophenyl ) 3.1 g of biphenyl-4-amine was obtained. (Yield: 42%)

1 H NMR (CDCl ₃ , 600 MHz) δ 7.61-7.57 (d, 4H), 7.53-7.50 (d, 4H), 7.44-7.41 (t, 4H), 7.33-7.31 (t, 2H), 7.29 (s, 1H ), 7.19-7.16 (d, 4H), 7.13-7.11 (d, 2H), 7.07-7.06 (d, 1H)

Manufacturing example  17. Intermediate (17) N- (biphenyl-4-yl) -N- (3- (4,4,5,5- Tetraethyl -1,3,2-dioxaboronlan-2-yl) Phenyl ) Biphenyl-4- Amine  synthesis

In the same manner as in Preparation Example 12, 3.1 g of Intermediate (16) prepared in Preparation Example 16 was added and reacted with N- (biphenyl-4-yl) -N- (3- (4,4,5,5-tetraethyl) 2 g of -1,3,2-dioxaborolan-2-yl) phenyl) biphenyl-4-amine were obtained. (Yield 77%)

1 H NMR (CDCl ₃ , 600 MHz) δ 7.65 (s, 1H), 7.59-7.57 (d, 4H), 7.55-7.54 (d, 1H), 7.49-7.47 (d, 4H), 7.43-7.40 (t, 4H ), 7.33-7.26 (m, 4H), 7.16-7.14 (d, 4H), 1.32 (s, 12H)

Manufacturing example  18. Synthesis of Intermediate 18

In the same manner as in Production Example 4, 10 g of dibenzofuran-4-boronic acid and 20 g of 4-bromo iodine benzene were added to the mixture, whereby 14.1 g of an intermediate (18) was obtained. (Yield: 94%)

_{1H NMR (CDCl 3, 600MHz)} δ 8.00-7.98 (d, 1H), 7.95-7.94 (d, 1H), 7.80-7.79 (d, 2H), 7.67-7.65 (d, 2H), 7.60-7.58 (d , 7.57-7.55 (d, 1H), 7.47-7.46 (t, 1H), 7.43-7.41 (t, 1H), 7.38-7.35

Manufacturing example  19. Synthesis of Intermediate (19)

In the same manner as in Production Example 17, 8 g of the intermediate (18) was added and reacted to obtain 7.7 g of the intermediate (19). (Yield: 84%)

_{1H NMR (CDCl 3, 600MHz)} δ 7.99-7.97 (d, 3H), 7.95-7.94 (d, 1H), 7.92-7.91 (d, 2H), 7.62-7.61 (d, 1H), 7.59-7.58 (d , 7.47-7.45 (t, 1H), 7.44-7.41 (t, 1H), 7.37-7.34 (t,

Manufacturing example  20. Synthesis of Intermediate 20

In the same manner as in Production Example 2, 4 g of Intermediate (19) and 4 g of 1,3-dibromo-2-iodobenzene were added thereto and reacted to obtain 2 g of Intermediate (20). (Yield: 40%)

_{1H NMR (CDCl 3, 600MHz)} δ 8.07-8.05 (d, 2H), 8.01-7.99 (d, 1H), 7.96-7.95 (d, 1H), 7.72-7.71 (d, 1H), 7.68-7.66 (d 2H), 7.65-7.64 (d, 1H), 7.49-7.44 (m, 2H), 7.39-7.38 (m, 3H), 7.11-7.08

Example  1. Synthesis of Compound (1)

질소 분위기 하의 250ml 둥근바닥 3구 플라스크에 제조예 1에서 제조된 중간체(1) 1.5g, 제조예 5에서 제조된 중간체(5) 3.6g, 테트라키스 트리페닐포스핀 팔라듐(0) 0.7g, 탄산칼륨 2.5g, 톨루엔 50ml와 메탄올 20ml를 넣고, 65℃로 4시간 교반한다. 반응액을 냉각 후 디클로로메탄과 물로 추출하고, 추출된 용액을 농축한다. 디클로로메탄과 n-헥산 혼합용매로 컬럼크로마토그래피 실시한 용액을 농축하고 재결정하여 화합물(1) 2.7g을 얻었다. (수율 90%)

1.5 g of intermediate (1) prepared in Preparation Example 1, 3.6 g of intermediate (5) prepared in Preparation Example 5, 0.7 g of tetrakis triphenylphosphine palladium (0) in a 250 ml round bottom three neck flask under nitrogen atmosphere, carbonic acid 2.5 g of potassium, 50 ml of toluene and 20 ml of methanol were added and stirred at 65 ° C for 4 hours. The reaction solution is cooled, extracted with dichloromethane and water, and the extracted solution is concentrated. The solution subjected to column chromatography with dichloromethane and n-hexane mixed solvent was concentrated and recrystallized to obtain 2.7 g of Compound (1). (Yield: 90%)

1 H NMR (CDCl ₃ , 600 MHz) δ 7.63 (s, 2H), 7.61-7.60 (d, 2H), 7.57 (s, 1H), 7.45-7.42 (t, 2H), 7.37-7.30 (m, 5H), 7.28-7.23 (m, 9H), 7.13-7.11 (d, 9H), 7.07-7.05 (d, 2H), 7.01-6.99 (t, 4H)

Example  2. Synthesis of Compound (6)

2.4g of compound (6) was obtained by the same method as the preparation method of Example 1 except that the intermediate (7) was used instead of the intermediate (5). (Yield: 80%)

1 H NMR (CDCl ₃ , 600 MHz) δ 7.58-7.57 (d, 2H), 7.43-7.40 (t, 4H), 7.34-7.32 (t, 1H), 7.16 (t, 1H), 7.12-7.10 (d, 2H ), 7.03-6.98 (m, 18H), 6.95-6.94 (d, 2H), 2.27-2.28 (s, 18H)

Example  3. Synthesis of Compound (2)

2.4 g of Compound (2) was obtained by the same method except that Intermediate (3) was used instead of Intermediate (1) in the preparation method of Example 2. (Yield: 87%)

1 H NMR (CDCl ₃ , 600 MHz) δ 8.33 (s, 1H), 8.17-8.16 (d, 1H), 7.63-7.57 (m, 5H), 7.53 (s, 2H), 7.47-7.44 (t, 1H), 7.43-7.41 (m, 3H), 7.31-7.29 (m, 1H), 7.16 (s, 1H), 7.13-7.12 (d, 2H), 7.07-7.06 (s, 2H), 7.04-7.00 (m, 16H ), 6.97-6.96 (dd, 2H)

Example  4. Synthesis of Compound (26)

1.4 g of Compound (26) was obtained by the same method except that Intermediate (4) was used instead of Intermediate (1) in the preparation method of Example 1. (Yield: 56%)

1 H NMR (CDCl ₃ , 600 MHz) δ 7.84-7.83 (d, 1H), 7.56-7.53 (t, 2H), 7.46-7.39 (m, 9H), 7.09-7.08 (d, 1H), 7.05-7.03 (t , 3H), 6.90-6.87 (m, 10H), 6.83-6.81 (d, 1H), 6.77-6.75 (t, 6H), 6.68-6.64 (m, 10H)

Example  5. Synthesis of Compound (3)

1.6 g of Compound (3) was obtained in the same manner as in Example 2, except that Intermediate (4) was used instead of Intermediate (1). (Yield: 74%)

1 H NMR (CDCl ₃ , 600 MHz) δ 7.90-7.89 (s, 1H), 7.84-7.83 (d, 1H), 7.59-7.57 (t, 4H), 7.53-7.52 (d, 4H), 7.46-7.40 (m , 7H), 7.33-7.32 (t, 2H), 7.27-7.24 (m, 2H), 7.10-7.07 (t, 2H), 6.93-6.60 (m, 14H), 2.25-2.23 (s, 18H)

Tg: 130 ℃

Example  6. Synthesis of Compound (14)

1.5 g of Compound (14) was obtained by the same method except that Intermediate (15) was used instead of Intermediate (1) in the preparation method of Example 2. (Yield: 73%)

Example  7. Synthesis of Compound (46)

In the same manner as in the preparation method of Example 2, 1.51 g of the intermediate (20) and 3.3 g of the intermediate (17) were added thereto, and reacted to obtain 2.6 g of the compound (46). (Yield: 74%)

1 H NMR (CDCl ₃ , 600 MHz): δ 7.94-7.93 (d, 1H), 7.85-7.83 (d, 1H), 7.81-7.80 (d, 2H), 7.65-7.64 (d, 1H), 7.43-7.41 ( d, 4H), 7.40-7.31 (m, 11H), 7.30-7.26 (m, 16H), 7.27-7.23 (m, 6H), 7.02-7.00 (d, 2H), 6.99-6.98 (d, 2H), 6.95-6.94 (d, 2H), 6.91-6.89 (d, 8H), 6.80 (s, 2H)

LC / Mass [M + H] ⁺ : 1112.8

Example  8. Synthesis of Compound (47)

In the same manner as in Example 2, 1.51 g of intermediate (20) and 1.85 g of 3- (9H-carbazol-9-yl) phenylboronic acid were added and reacted to obtain 1.8 g of compound (47). (71% yield)

1 H NMR (CDCl ₃ , 600 MHz): δ 8.08 (s, 2H) 8.07-8.05 (d, 2H), 7.91-7.90 (d, 1H), 7.81-7.79 (d, 1H), 7.65-7.64 (d, 2H ), 7.60-7.59 (d, 1H), 7.56-7.54 (d, 2H), 7.52-7.49 (m, 8H), 7.44-7.43 (d, 1H), 7.38-7.33 (m, 8H), 7.33-7.27 (m, 2H), 7.21-7.16 (m, 4H), 7.13-7.11 (m, 4H)

LC / Mass [M + H] < ⁺ >: 805.9

Example  9. Synthesis of Compound (48)

1.51 g of the intermediate (20) and 0.9 g of 3- (9H-carbazol-9-yl) phenylboronic acid were reacted in the same manner as in the preparation method of Example 2, followed by 3- (diphenylamino) phenylo in the same manner. 1 g of lonic acid was added and reacted to obtain 1 g of compound (48). (Yield: 40%)

1 H NMR (CDCl ₃ , 600 MHz): δ 8.08 (s, 2H) 8.07-8.05 (d, 2H), 7.91-7.90 (d, 1H), 7.81-7.79 (d, 1H), 7.65-7.64 (d, 2H ), 7.60-7.59 (d, 1H), 7.56-7.54 (d, 2H), 7.52-7.49 (m, 8H), 7.44-7.43 (d, 1H), 7.38-7.33 (m, 8H), 7.33-7.27 (m, 2H), 7.21-7.16 (m, 4H), 7.16-7.15 (d, 2H), 7.13-7.11 (m, 4H)

LC / Mass [M + H] ⁺ : 806.5

Device Example  1. Compound 1 was dissolved in a second hole With transport layer  Containing Organic electroluminescent device  Produce

The glass substrate coated with ITO (Indium Tin Oxide) thin film with a thickness of 100 nm was ultrasonically cleaned with isopropyl alcohol solvent, dried and transferred to a plasma cleaner, the substrate was cleaned using oxygen plasma for 5 minutes, and the substrate was vacuum- Respectively.

DNTPD [N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolylamino) -phenyl] -biphenyl-4,4 on an ITO substrate using the prepared ITO transparent electrode as an anode '-diamine] was vacuum deposited to form a hole injection layer having a thickness of 55 nm. Subsequently, NPB [N, N'-Di (naphthalen-1-yl) -N, N'-diphenyl-benzidine] was vacuum deposited to a thickness of 20 nm as a primary hole transport layer, and as a secondary hole transport layer on the primary hole transport layer. Compound 1 was formed to a thickness of 10 nm. CBP [4,4-N, N-dicarbazolebiphenyl] is used as a host on the secondary hole transport layer and doped with Ir (PPy) 3 [tris (2-phenylpyridine) iridium] at a volume of 6% by volume. By vacuum deposition to a thickness of 25nm to form a light emitting layer.

Thereafter, Bphen [4,7-diphenyl-1,10-phenanthroline] was formed to a thickness of 30 nm as an electron transport layer on the emission layer. Liq [lithium quinolate] 2 nm and Al 100 nm were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby fabricating an organic electroluminescent device.

Device Example  2. Secondary Hole in Compound 2 With transport layer  Containing Organic electroluminescent device  Produce

An organic light emitting diode was manufactured according to the same method as Device Example 1 except for using Compound 2 instead of Compound 1.

Device Example  3. Secondary Hole in Compound 3 With transport layer  Containing Organic electroluminescent device  Produce

An organic light emitting display device was manufactured according to the same method as Device Example 1, except that Compound 3 was used instead of Compound 1.

Device Example  4. Secondary Holes in Compound 46 With transport layer  Containing Organic electroluminescent device  Produce

An organic light emitting diode was manufactured according to the same method as Device Example 1 except for using Compound 46 instead of Compound 1.

Device Example  5. Secondary Holes for Compound 47 With transport layer  Containing Organic electroluminescent device  Produce

An organic light emitting diode device was manufactured according to the same method as Device Example 1, except that Compound 47 was used instead of Compound 1.

Device Example  6. Second Hole in Compound 48 With transport layer  Containing Organic electroluminescent device  Produce

An organic light emitting diode was manufactured according to the same method as Device Example 1 except for using Compound 48 instead of Compound 1.

Device comparison example  One. NPB The second hole With transport layer  Containing Organic electroluminescent device  Produce

An organic light emitting diode was manufactured according to the same method as Example 1 except for using NPB instead of Compound 1.

The structural formulas of DNTPD, NPB, CBP, and Bphen used in the above examples are as follows.

Test Example . The organic electroluminescent device  Character analysis

Device characteristics were analyzed at 1000 cd / m ² luminance of Device Examples 1 to 6 and Device Comparative Example 1, and are shown in Table 1 below.

Current density

For the organic light emitting device manufactured, the current value was measured in a unit device using a current-voltmeter (Keithley 2635A Source Meter) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result .

Luminance efficiency

For the organic light-emitting device manufactured, the luminance at that time was measured using a luminance meter (Minolta CS-2000) while increasing the voltage from 0 V to 10 V, and the measured luminance value was divided by the current value to obtain a result.

Color coordinates

Color coordinates were measured using a luminance meter (Minolta CS-2000) to obtain the results.

Secondary hole transport layer material Current density
(mA / cm ² ) Luminance efficiency
(cd / A) Color coordinates
(CIE (x, y)) Device Embodiment 1 Compound 1 7.69 37.1 0.31,0.60 Device Example 2 Compound 2 4.62 35.1 0.32, 0.61 Device Embodiment 3 Compound 3 3.99 39.4 0.32, 0.61 Device Example 4 Compound 46 9.26 35.5 0.31,0.61 Element Embodiment 5 Compound 47 8.86 37.1 0.31,0.62 Device Example 6 Compound 48 9.16 35.9 0.31,0.62 Device Comparative Example 1 NPB 10.65 30.9 0.31,0.61

According to Table 1, as a result of using the compounds 1 to 3, and 46 to 48 according to the present invention in the organic light emitting device as a secondary hole transport layer material, it was confirmed that the excellent properties compared to the conventional material NPB.

Claims (12)

A compound for an organic electroluminescence device represented by any one of Structural Formulas 1 to 6 below.

In the above Structural Formulas 1 to 6,
R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,
m is 0 or 1,
n is 0 or 1,
m + n = 1,
R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
A ¹ and A ² may be the same or different from each other, and A ¹ and A ² each independently represents a valence bond or

ego,
R ¹⁸ and R ¹⁹ may be the same as or different from each other, R ¹⁸ and R ¹⁹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,
a1 is 0 or 1,
a2 is 0 or 1; The method of claim 1,
The organic electroluminescent device compound is represented by any one of the following structural formulas 7 to 9,

In the above Structural Formulas 7 to 9,
R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,
m is 0 or 1,
n is 0 or 1,
m + n = 1,
R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
A < ^{1 >} is a valence bond or

ego,
R ¹⁸ and R ¹⁹ may be the same as or different from each other, R ¹⁸ and R ¹⁹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group,
lt; 1 > is 0 or 1. The method of claim 1,
The compound for an organic electroluminescence device is represented by the following structural formula 10,
[Structure 10]

In the above formula 1,
R ¹ and R ² may be the same as or different from each other, R ¹ and R ² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R ¹ is an adjacent carbon atom of R ¹ bonded to a carbon atom Further bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted Form a fused C1 to C30 heteroaryl group,
m is 0 or 1,
n is 0 or 1,
m + n = 1,
R ³ to R ¹⁴ may be the same as or different from each other, R ³ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group,

or

Or at least one of R ³ to R ¹⁴ is further bonded with a neighboring carbon atom of the carbon atom to which one is bonded to a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 To C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ¹ and Ar ² are bonded to each other and substituted or unsubstituted with a nitrogen atom therebetween. Form a substituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ¹ and Ar ² is selected from the carbon atom at the β-position of the nitrogen atom to which any one is bonded; May be further joined to form a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
R ¹⁵ to R ¹⁷ may be the same as or different from each other, R ¹⁵ to R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted A compound for an organic electroluminescent device, wherein the compound is a substituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. The method of claim 1,
R ¹ and R ² may be the same or different from each other, and R ¹ and R ² are each independently a hydrogen atom,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or R ¹ is adjacent to a carbon atom to which R ¹ is bonded A substituted or unsubstituted fused C3 to C30 cycloalkyl group further substituted with a carbon atom, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or To form an unsubstituted fused C1 to C30 heteroaryl group,
Y ¹ and Y ² may be the same or different from each other, Y ¹ and Y ² are each independently an oxygen atom, a sulfur atom,

or

ego,
Ar ⁷ Is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, RTI ID = 0.0 > Cl-C30 < / RTI > heteroaryl group,
R ²⁹ and R ³⁰ may be the same as or different from each other, R ²⁹ and R ³⁰ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
Ar ³ to Ar ⁶ may be the same as or different from each other, Ar ³ to Ar ⁶ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar ³ and Ar ⁴ , and Ar ⁵ and Ar ⁶ are each bonded to each other Or a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group together with a nitrogen atom of N, or at least one of Ar ³ to Ar ⁶ is a nitrogen to which any one is bonded Further bonding with a carbon atom at the β-position of the atom forms a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group May,
R ²⁰ to R ²⁸ may be the same as or different from each other, R ²⁰ to R ²⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
q is 0 or 1 compound for an organic light emitting device. 5. The method of claim 4,
Ar ³ to Ar ⁶ may be the same as or different from each other, Ar ³ to Ar ⁶ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar ³ to Ar ⁶ is a β of the nitrogen atom to which one is bonded A compound for an organic electroluminescent device, further comprising a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group or a substituted or unsubstituted fused C1 to C30 heteroaryl group. The method of claim 1,
Ar ¹ and Ar ² may be the same as or different from each other, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, a compound for an organic light emitting device. The method of claim 1,
Wherein the compound for an organic electroluminescence device is any one selected from compounds 1 to 48 represented by the following formula.

An organic electroluminescent device comprising the compound for organic electroluminescent device according to claim 1. A first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode, the organic electroluminescent device comprising:
The organic electroluminescent device according to claim 1, wherein the at least one organic layer selected from the single or plural organic layers comprises the compound for organic electroluminescent devices according to claim 1. 10. The method of claim 9,
Wherein the single or plural organic layers include a light emitting layer. 10. The method of claim 9,
Wherein the plurality of organic layers include a light emitting layer and the plurality of organic layers further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer and a hole injecting layer Organic electroluminescent device. 11. The method of claim 10,
Wherein the light emitting layer comprises a host and a dopant.

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