TW201412715A - Compound for organic electroluminescent device and organic electroluminescent device including the same - Google Patents

Abstract

This invention relates to a compound for an organic electroluminescent device represented by Chemical Formula 1 below and to an organic electroluminescent device including the same. This compound for an organic electroluminescent device has high thermal stability, high triplet energy and hole transport capability, and the organic electroluminescent device including the same is improved in thermal stability and light emission efficiency. When this compound is used as a hole transport layer material, a triplet exciton of a phosphorescent light emitting material is confined, thus improving efficiency of the organic electroluminescent device.

Description

Compound for organic electroluminescent device and organic electroluminescent device comprising the same

The present invention relates to a compound for use in an organic electroluminescent device and an organic electroluminescent device comprising the same, and more particularly to an amine-based compound having a heterocyclic structure and used in an organic electroluminescent device and An organic electroluminescent device comprising the amine compound.

Organic electroluminescent (EL) devices have a relatively simple structure, various processing advantages, high brightness, excellent viewing angle properties, faster reaction rates, and other flat panel displays (such as liquid crystal displays (LCD), plasma Display panels (PDPs), field emission displays (FEDs, etc.) are completely developed in comparison to lower driving voltages, so as to be utilized as light sources for flat panel displays (eg, wall mountable televisions, etc.) or as backlight units for displays, illumination , advertising billboards, etc.

Typically, when a direct current voltage is applied to the organic EL device, electrons injected from the anode and electrons injected from the cathode recombine to form an electron-hole pair, That is, excitons. When the excitons return to the stable ground state, the energy corresponding thereto is transferred to the luminescent material and thereby converted into light.

In order to increase the efficiency and stability of the organic EL device, CWTang et al. of Eastman Kodak Company have fabricated an organic EL operating at a low voltage by forming a tandem organic film between two opposite electrodes. After the device (CWTang, SA Vanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987), extensive and intensive research into organic materials for organic EL devices having a multilayer film structure has continued. The efficiency and lifetime of such tandem organic EL devices are closely related to the molecular structure of the materials used for the films. For example, quantum efficiency can vary greatly depending on the structure of the material used for the film, particularly the host material, the hole transport layer material, or the electron transport layer material. When the thermal stability of the material is reduced, the material may crystallize at high temperatures or at the driving temperature, which undesirably shortens the life of the device.

Hole-transporting materials that are currently known to be useful for organic EL devices are problematic because the film formed from the hole-transporting material using vacuum deposition is thermally and electrically unstable, and thus may be rapidly due to heat generated after the device is driven. The crystals are crystallized, and the film material may also change, undesirably degrading the luminous efficiency of the device. In addition, there may be more and more non-illuminating portions called dark spots, and the voltage may be increased under constant current driving, and the device is not ideally damaged.

Meanwhile, the organic EL device using the phosphorescent luminescent material does not limit the triplet excitons generated in the luminescent material of the luminescent layer due to the low triplet energy, and the luminous efficiency of the device is undesirably lowered.

Accordingly, it is an object of the present invention to provide a compound for an organic EL device which can have high thermal stability, high triplet energy, and hole transporting ability.

Another object of the present invention is to provide an organic EL device comprising the above compound, and thus improving thermal stability and luminous efficiency, and wherein the above compound is used as a material for a hole transport layer, thereby limiting phosphorescence The triplet excitons of the luminescent material ultimately improve the efficiency of the organic EL device.

In order to achieve the above object, an aspect of the present invention provides a compound for an organic EL device, which is represented by the following Chemical Formula 1.

In Chemical Formula 1, Ar ¹ to Ar ⁴ are the same or different from each other, and Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, and a substitution. Or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C1 to C30 heteroaryl, or Ar ¹ and Ar ² and Ar ³ and Ar ⁴ , respectively, forming a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group having an intermediate nitrogen atom together, and R ¹ is a hydrogen atom, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or Unsubstituted C1 to C30 heteroaryl, R ² to R ⁵ are the same or different from each other, and R ² to R ⁵ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C1 to C30 a heteroaryl group, or at least one of R ² to R ⁵ , is further coupled to a carbon atom adjacent to a carbon atom to which it is attached to form a substituted or unsubstituted fused C 3 to C 30 cycloalkyl group, substituted or unsubstituted Substituted fused C1 to C30 heterocycloalkyl, substituted or unsubstituted fused C6 to C30 aryl, or substituted or unsubstituted fused C1 to C30 heteroaryl, X and Y being the same or different from each other, And X and Y are each independently a valence bond or Wherein Z is a carbon atom or a ruthenium atom, R ⁶ and R ⁷ are the same or different from each other, and R ⁶ and R ⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted a 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, q is 0. Or 1, m is 0 or 1, n is 0 or 1, and m+n≠0.

According to a preferred embodiment of the present invention, the compound for an organic EL device is represented by any one of the following Chemical Formulas 2 and 3.

In Chemical Formulas 2 and 3, Ar ¹ to Ar ⁴ are the same or different from each other, and Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group. , substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C1 to C30 heteroaryl, or Ar ¹ and Ar ² and Ar ³ And Ar ⁴ are respectively linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group having an intermediate nitrogen atom together, and R ¹ is a hydrogen atom, a substituted or Unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted Or unsubstituted C1 to C30 heteroaryl, R ² to R ⁵ are the same or different from each other, and R ² to R ⁵ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, substituted or not Substituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C1 C30 heteroaryl group, or R ² to R ⁵ is at least one carbon atom is further coupled with carbon atoms adjacent thereto are linked to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or Unsubstituted fused C1 to C30 heterocycloalkyl, substituted or unsubstituted fused C6 to C30 aryl, or substituted or unsubstituted fused C1 to C30 heteroaryl, and X and Y are the same or Different, and X and Y are each independently a valence bond or Wherein Z is a carbon atom or a halogen atom, and R ⁶ and R ⁷ are the same or different from each other, and R ⁶ and R ⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted a 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.

According to a preferred embodiment of the present invention, the compound for an organic EL device is represented by any one of the following Chemical Formulas 4 and 5.

[Chemical Formula 4]

In Chemical Formulas 4 and 5, Ar ¹ to Ar ⁴ are the same or different from each other, and Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group. , substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C1 to C30 heteroaryl, or Ar ¹ and Ar ² and Ar ³ And Ar ⁴ are respectively linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group having an intermediate nitrogen atom together, and R ¹ is a hydrogen atom, a substituted or Unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted Or unsubstituted C1 to C30 heteroaryl, R ² to R ⁵ are the same or different from each other, and R ² to R ⁵ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, substituted or not Substituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C1 C30 heteroaryl group, or R ² to R ⁵ is at least one carbon atom is further coupled with carbon atoms adjacent thereto are linked to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or Unsubstituted fused C1 to C30 heterocycloalkyl, substituted or unsubstituted fused C6 to C30 aryl, or substituted or unsubstituted fused C1 to C30 heteroaryl, and X and Y are the same or Different, and X and Y are each independently a valence bond or Wherein Z is a carbon atom or a halogen atom, and R ⁶ and R ⁷ are the same or different from each other, and R ⁶ and R ⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted a 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.

According to a preferred embodiment of the present invention, the compound for an organic EL device is represented by any one of the following Chemical Formulas 6 and 7.

In Chemical Formulas 6 and 7, Ar ¹ to Ar ⁴ are the same or different from each other, and Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group. , substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C1 to C30 heteroaryl, or Ar ¹ and Ar ² and Ar ³ And Ar ⁴ are respectively linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group having an intermediate nitrogen atom together, and R ¹ is a hydrogen atom, a substituted or Unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted Or unsubstituted C1 to C30 heteroaryl, R ² to R ⁵ are the same or different from each other, and R ² to R ⁵ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, substituted or not Substituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C1 C30 heteroaryl group, or R ² to R ⁵ is at least one carbon atom is further coupled with carbon atoms adjacent thereto are linked to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or Unsubstituted fused C1 to C30 heterocycloalkyl, substituted or unsubstituted fused C6 to C30 aryl, or substituted or unsubstituted fused C1 to C30 heteroaryl, and X and Y are the same or Different, and X and Y are each independently a valence bond or Wherein Z is a carbon atom or a halogen atom, and R ⁶ and R ⁷ are the same or different from each other, and R ⁶ and R ⁷ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted a 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.

In a preferred embodiment of the present invention, Ar ¹ to Ar ⁴ are the same or different from each other, and Ar ¹ to Ar ⁴ are each independently 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 Ar ¹ and Ar ² and Ar ³ and Ar ^{4 is} respectively linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group having an intermediate nitrogen atom together, wherein R ⁸ to R ¹³ are the same or different from each other And R ⁸ to R ¹³ 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 C1 to C30 heterocycloalkane. A substituted, 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 may include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted one. Naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracene A benzyl, substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted fluorenyl group.

Examples of the substituted or unsubstituted C1 to C30 heteroaryl group may include a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted one. Thiophenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted imidazo[1,2-a]pyridine Base, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted phenothiazine, substituted or unsubstituted cyanozinyl, substituted or unsubstituted Carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl, substituted or not Substituted oxadiazolyl, substituted or unsubstituted oxatriazole, substituted or unsubstituted thiatriazole, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted pyrazinyl , substituted or unsubstituted pyridazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted a substituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted naphthylpyridyl group, a substituted or unsubstituted quinone A substituted, unsubstituted quinazolinyl group, a substituted or unsubstituted acridine group, or a substituted or unsubstituted morpholinyl group. More useful are substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted pyrrolyl , substituted or unsubstituted benzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted imidazo[1,2-a]pyridyl, substituted or unsubstituted benzimidazolyl , substituted or unsubstituted carbazolyl, An substituted or unsubstituted phenothiazine group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted oxazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.

According to a preferred embodiment of the present invention, the compound for an organic EL device is selected from any one of the compounds 1 to 65 represented by the following chemical formula.

According to an embodiment of the present invention, an organic electroluminescence (EL) device including a compound for an organic EL device according to the present invention can be provided.

According to an embodiment of the present invention, an organic EL device may include a first electrode, a second electrode, and a single organic layer or a plurality of organic layers interposed between the first electrode and the second electrode, wherein one or more The organic layer selected from the single organic layer or the plurality of organic layers may include a compound for an organic EL device according to the present invention.

According to an embodiment of the invention, the single organic layer or the plurality of organic layers may comprise a light-emitting layer.

According to an embodiment of the present invention, the plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transport layer, and electricity. One or more of the holes are injected into the layer.

According to an embodiment of the invention, the light emitting layer may include a body and a dopant.

According to an embodiment of the invention, a compound comprising one or more derivatives having a substituted phenyl group is provided, such that it is possible to provide various derivatives, such that the compound can be adjusted Nature. When this compound is contained in the organic layer of the organic EL device, various properties can be exhibited. Further, the thermal stability and luminous efficiency of the organic EL device using the compound can be improved, and the use of the compound as a material for the hole transport layer can limit the triplet excitons of the phosphorescent material, with the result that the efficiency of the organic EL device is improved.

1‧‧‧Organic EL device

110‧‧‧First electrode

130‧‧‧Organic layer

131‧‧‧Electronic injection layer

132‧‧‧Electronic transport layer

133‧‧‧ hole barrier

134‧‧‧Lighting layer

135‧‧‧Electronic barrier

136‧‧‧ hole transport layer

137‧‧‧ hole injection layer

150‧‧‧second electrode

The above and other objects, features and advantages of the present invention will become more apparent from And Fig. 2 is a cross-sectional view showing an organic EL device according to another embodiment of the present invention.

The invention may be variously modified, and various embodiments may be made and the specific embodiments are described. However, the following description is not intended to limit the invention to the specific embodiment, and is intended to include all modifications, equivalents or alternatives within the spirit and scope of the invention. Further, in the description of the present invention, when it is determined that the detailed description of the related art may obscure the gist of the present invention, the description of the related art will be deleted.

Also, in the following description, the terms "first", "second" and the like are used to distinguish some components from other components, but the configuration of such components should not be construed as being limited by the terms. For example, within the scope of the invention, a first component may be referred to as a second component and a second component may be referred to as a first component.

Also, when any component is referred to as being "formed" or "stacked" on another component, the component can be attached directly to the entire surface or surface of the other component, or another component can be Extra inserts in between.

Unless otherwise stated, the singular representation includes the plural. In this application, the terms "including" and "having" are used to indicate the specification. The existence of features, quantities, steps, operations, components, components, or combinations of the above described are not intended to exclude the existence or additional possibilities of one or more different features, quantities, steps, operations, components, components or combinations of the above. Sex.

As used herein, unless otherwise defined, the term "valent bond" means a single bond, a double bond, or a reference bond.

As used herein, unless otherwise defined, the term "substituted" means that at least one hydrogen on a substituent or compound is oxime, halo, hydroxy, amine, C1 to C30 amine, nitro, C1 to C30. Mercapto, C1 to C30 alkyl, C1 to C30 alkyl fluorenyl, C3 to C30 cycloalkyl, C1 to C30 heterocycloalkyl, C6 to C30 aryl, C1 to C30 heteroaryl, C1 to C20 alkoxy , C1 to C10 trifluoroalkyl or cyano substituted.

Further, in the substituted halo, hydroxy, amine, C1 to C30 amine, C3 to C30 decyl, C1 to C30 alkyl, C1 to C30 alkyl fluorenyl, C3 to C30 cycloalkyl, C6 to C30 aryl In the C1 to C20 alkoxy group, the C1 to C10 trifluoroalkyl group or the cyano group, two adjacent substituents may be fused to form a ring.

As used herein, unless otherwise defined, the term "hetero" means a functional group containing from 1 to 4 heteroatoms selected from the group consisting of N, O, S, and P, with the remainder being carbon.

As used herein, unless otherwise defined, the term "combination of the above" means that two or more substituents are fused to each other by a linker or two or more substituents.

As used herein, unless otherwise defined, the term "hydrogen" means hydrogen, hydrazine or hydrazine.

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

The alkyl group may be a "saturated alkyl group" without any double bond or reference bond.

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

The term "alkenylene group" means a functional group having at least one carbon-carbon double bond between at least two carbon atoms, and the term "alkynylene group" means at least two carbons A functional group having at least one carbon-carbon bond between atoms. The alkyl group may be branched, linear or cyclic, whether saturated or unsaturated.

The alkyl group may be a C1 to C30 alkyl group, preferably a C1 to C20 alkyl group, more preferably a C1 to C10 alkyl group, and still more preferably a C1 to C6 alkyl group.

For example, a C1 to C4 alkyl group means an alkyl chain having 1 to 4 carbon atoms, particularly selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and secondary. An alkyl chain of the group consisting of a butyl group and a tertiary butyl group.

Specific examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, vinyl, propenyl, butenyl, cyclopropyl , cyclobutyl, cyclopentyl, cyclohexyl and the like.

The "amino group" includes an arylamino group, an alkylamino group, an aralkylamino group or an alkylarylamine group.

The term "cycloalkyl" refers to a monocyclic or fused polycyclic (ie, a ring that shares a pair of adjacent carbon atoms) functional groups.

The term "heterocycloalkyl" means a cycloalkyl group containing from 1 to 4 heteroatoms selected from the group consisting of N, O, S and P, the balance being carbon. In the case where the heterocycloalkyl group is a fused ring, each ring may contain from 1 to 4 hetero atoms.

The term "aryl" means a cyclic functional group in which all of the ring atoms have a p-orbital domain, and these p-orbital domains form a conjugation. Specific examples of the aromatic group include an aryl group and a heteroaryl group.

The term "aryl" refers to a monocyclic or fused polycyclic (ie, a ring that shares a pair of adjacent carbon atoms) functional groups.

The term "heteroaryl" means an aryl group containing from 1 to 4 hetero atoms selected from the group consisting of N, O, S and P, the balance being carbon. In the case where the heteroalkyl group is a fused ring, each ring may contain from 1 to 4 hetero atoms.

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

When an alkyl group and an aryl group are used in a combination such as "alkylaryl" or "aralkyl", "alkyl" and "aryl" have the above meanings, respectively.

The term "aralkyl" means an aryl-substituted alkyl radical, such as a benzyl group, and is incorporated into an alkyl group.

The term "alkaryl" means an alkyl-substituted aromatic radical and is incorporated into an aryl group.

The description of the embodiments of the present invention with reference to the accompanying drawings, in which the same or similar components are referred to, and the repeated description of the embodiments are omitted.

Referring to Figures 1 and 2, an organic EL device 1 comprising a compound for use in an organic EL device according to the present invention can be provided in accordance with an embodiment of the present invention.

According to another embodiment of the present invention, an organic EL device includes a first electrode 110, a second electrode 150, and the first electrode and the second electrode A single organic layer or a plurality of organic layers 130 may be interposed, and one or more organic layers selected from the single organic layer or the plurality of organic layers 130 may include a compound for use in an organic EL device according to the present invention.

As such, the single organic layer or the plurality of organic layers 130 may include the light emitting layer 134.

The plurality of organic layers 130 includes a light emitting layer 134, and the plurality of organic layers 130 may further include an electron injecting layer 131, an electron transporting layer 132, a hole blocking layer 133, an electron blocking layer 135, a hole transport layer 136, and a hole. One or more of the layers 137 are implanted.

Similarly, one or more selected from the group consisting of the electron injection layer 131, the electron transport layer 132, the hole barrier layer 133, the light emitting layer 134, the electron blocking layer 135, the hole transport layer 136, and the hole injection layer 137 may be selected. Formed as a plurality of layers.

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

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

The anode material of the organic EL device according to the present invention may include a metal, an alloy, a conductive compound or a mixture of the above having a work function of 4 electron volts (eV) or higher. Specific examples of the anode material may include gold (Au) metal or a transparent conductive material such as CuI, ITO (Indium Tin Oxide), SnO _{2 ,} and ZnO. The thickness of the anode film is preferably set to 10 to 200 nm.

The cathode material of the organic EL device according to the present invention may include a metal, an alloy, a conductive compound or a mixture of the above having a work function of less than 4 eV. Specific examples of the cathode material may include sodium (Na), sodium-potassium (Na-K) alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy or aluminum alloy. In addition, aluminum/AlO ₂ , aluminum/lithium, magnesium/silver or magnesium/indium can also be used. The thickness of the cathode film is preferably set to 10 to 200 nm.

In order to increase the luminous efficiency of the organic EL device, one or more electrodes preferably have a light transmittance of 10% or more. The sheet resistance of the electrode is preferably several hundred Ω/mm or less. The thickness of the electrode falls within the range of 10 nm to 1 μm, preferably 10 to 400 nm. Such an electrode may be formed into a film form by vapor deposition (for example, chemical vapor deposition (CVD), physical vapor deposition (PVD), or the like) or sputtering method using the above electrode material.

When a compound for an organic EL device according to the present invention is used in order to be suitable for the purpose of the present invention, a conventional hole transporting material, a hole injecting material, a light emitting layer material, a host material for a light emitting layer, an electron transporting material, and an electron The injection material may be used alone in each organic layer or may be used in combination with a compound for use in an organic EL device according to the present invention.

Examples of the hole transporting material may include porphyrin compound derivatives including N,N-dicarbazolyl-3,5-benzene (mCP), poly(3,4-ethylenedioxythiophene): poly(styrenesulfonate) Acid salt) (PEDOT:PSS), N,N'-bis(1-naphthyl--N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'- Bis(3-methylphenyl)-4,4'-diaminobiphenyl (TPD), N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diamino Biphenyl, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'- Diaminobiphenyl, 1,10,15,20-tetraphenyl-21H, 23H-porphyrin copper (II), etc.; triarylamine derivative, including polymerization having an aromatic tertiary amine in a main chain or a side chain 1,1-bis(4-di-p-tolylamidophenyl)cyclohexane, N,N,N- Tris(p-tolyl)amine and 4,4',4'-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine; carbazole derivatives, including N- Phenyl oxazole and polyvinyl carbazole; indigo derivatives, including metal-free indigo and beryllium bronze; starburst amine derivatives; enaminostilbene derivatives, styrylamine compounds containing aromatic tertiary amines Derivatives; polydecane, etc.

Examples of the electron transporting material may include diphenylphosphine oxide-4-(triphenylindenyl)phenyl (TSPO1), Alq ₃ , 2,5-diaryl sylol derivative, (PyPySPyPy) ), a perfluorinated compound (PF-6P), an octasubstituted cyclooctatetraene compound (COT), and the like.

In the organic EL device according to the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be provided in a single layer form containing one or more of the above compounds, or may be different The compound is provided in the form of a plurality of stacked layers.

The luminescent material may include, for example, a photoluminescent phosphor material, a fluorescent brightener, a laser dye, an organic scintillator, and a fluorescent analysis reagent. Specific examples of the luminescent material include a carbazolyl compound, a phosphine oxide compound, a carbazolyl phosphine oxide compound, and a polyaromatic compound (including bis((3,5-difluoro-4-cyanophenyl)pyridine) hydrazine. Pyridinecarboxylic acid (FCNIrpic), tris(8-hydroxyquinoline)aluminum (Alq3), ruthenium, phenanthrene, anthracene, benzophenanthrene, anthracene, anthracene, erythridene and quinophthalone), oligomeric benzene compounds (including four Biphenyl), scintillator for liquid scintillation (including 1,4-bis(2-methylstyryl)benzene, 1,4-bis(4-methylstyryl)benzene, 1,4-double (4-methyl-5-phenyl-2-oxazolyl)benzene, 1,4-bis(5-phenyl-2-oxazolyl)benzene, 2,5-bis(5-tert-butyl- 2-benzoxazolyl)thiophene, 1,4-diphenyl-1,3-butadiene, 1,6-diphenyl-1,3,5-hexanetriene and 1,1,4, 4-tetraphenyl-1,3-butadiene), oxin derivative Metal complex, coumarin dye, dicyanomethylene piperazine dye, dicyanomethylene thiopyran dye, polymethine dye, oxobenzanthracene dye, two A xanthene dye, a carbostyryl dye, an anthraquinone dye, an oxazine compound, a stilbene derivative, a spiro compound, an oxadiazole compound, and the like.

Each layer of the organic EL device according to the present invention may be provided in the form of a film using a conventional process (e.g., vacuum deposition, spin coating or casting), or may be fabricated using each layer material. The thickness of each layer is not particularly limited, but may be appropriately set depending on the nature of the material, and is typically measured in the range of 2 to 5000 nm.

Since the compound for an organic EL device according to the present invention can be subjected to vacuum deposition, the film formation process is simple, and a uniform film substantially free of pin holes can be easily obtained.

A better understanding of the present invention (on the synthesis of a compound for an organic EL device and the manufacture of an organic EL device including the same) can be obtained by the following examples, which are presented to illustrate the present invention, rather than being This is to be construed as limiting the invention.

[Example]

Preparation Example 1. Synthesis of Intermediate 1 (3-Bromo-tert-butyl-9H-carbonylcarbazole)

A 1 liter round bottom three-necked flask under nitrogen atmosphere was charged with 12.3 g of 3-bromocarbazole, 16.4 g of t-butyldicarbazole, 0.9 g of 4-dimethylaminopyridine, and 850 ml of THF. And stirred at room temperature for 3 hours. The reaction solution was concentrated, and then subjected to column chromatography using n-hexane to obtain 16.1 g of Intermediate 1 (yield 93%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 8.27 (d, 1H), 8.19 (d, 1H), 8.08 (d, 1H), 7.92 (d, 1H), 7.54 (dd, 1H), 748 (td, 1H ), 7.35 (t, 1H), 1.76 (s, 9H)

Preparation Example 2. Synthesis of Intermediate 2 (3-Diphenylamino-9H-tert-butylcarbonylcarbazole)

In a 500 ml round bottom three-necked flask under nitrogen atmosphere, 16.1 g of intermediate 1, 7.9 g of diphenylamine, 0.7 g of tris(dibenzylideneacetone)dipalladium (0), 1.9 g were placed. 15% tri(tert-butyl)phosphine, 29.2 g of cesium carbonate and 300 ml of toluene were refluxed for 24 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 13.1 g of Intermediate 2 (yield 64%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 8.29 (d, 1H), 8.19 (d, 1H), 7.82 (d, 1H), 7.73 (s, 1H), 7.44 (t, 1H), 7.28 (t, 1H) ), 7.25-7.23 (m, 5H), 7.11 (d, 4H), 6.99 (t, 2H), 1.74 (s, 9H)

Preparation Example 3. Synthesis of Intermediate 3(3-Diphenylamino-9H-carbazole)

In a 250 ml round bottom three-necked flask under a nitrogen atmosphere, 9.0 g of an intermediate 2, 0.44 g of anisole, 50 ml of trifluoroacetic acid and 80 ml of dichloromethane were placed, and stirred at room temperature for 30 minutes. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and then neutralized with a sodium bicarbonate aqueous solution, and then the organic layer was removed from water, filtered, and concentrated. The concentrated solution was recrystallized from dichloromethane and methanol, thus obtaining 4.7 g of Intermediate 3 (yield 68%).

¹ H NMR (Acetone, d ₆ , 600 MHz) δ 10.36 (s, 1H), 8.1 (d, 1H), 7.89 (d, 1H), 7.49 (t, 2H), 7.35 (t, 1H), 7.23-7.19 (m, 4H), 7.16 (dd, 1H), 7.11 (t, 1H), 7.02 (d, 4H), 6.91 (t, 2H)

Preparation Example 4. Synthesis of Intermediate 4 (9-(3,5-Dibromophenyl)-3-diphenylamino-9H-indazole)

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 2.5 g of 1,3-dibromo-5-fluorobenzene, 3.3 g of intermediate 3, 0.8 g of 60% sodium hydride and 50 ml of DMF were placed. It was stirred at 110 ° C for 4 hours. After the completion of the reaction, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane, and then the organic layer was removed from water and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 4.3 g of Intermediate 4 (yield 75%).

Preparation Example 5. Synthesis of Intermediate 5 (9-(3-Bromo-5-fluorophenyl)-9H-carbazole)

In a 500 ml round bottom three-necked flask under nitrogen atmosphere, 29 g of 1-bromo-3,5-difluorobenzene, 8.5 g of carbazole, 4.0 g of 60% sodium hydride and 250 ml of DMF were placed. Stir at 110 ° C for 4 hours. After the completion of the reaction, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane, and then the organic layer was removed from water and filtered. Filtrate Concentration and column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 8.6 g of Intermediate 5 (yield 50%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 8.13 (d, 2H), 7.57 (s, 1H), 7.43 (d, 4H), 7.36-7.30 (m, 4H)

Preparation Example 6. Synthesis of Intermediate 6 (1,3-Didiphenylamino-5-fluorobenzene)

In a 250 ml round bottom three-necked flask under nitrogen atmosphere, 5.0 g of 1,3-dibromo-5-fluorobenzene, 6.7 g of diphenylamine, and 0.2 g of tris(dibenzylideneacetone) were placed. Di-palladium (0), 0.3 g of 15% tris(tert-butyl)phosphine, 7.6 g of sodium t-butoxide and 100 ml of toluene were stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then recrystallized from dichloromethane and methanol to give 5.5 g of Intermediate 6 (yield 65%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 7.23 (t, 8H), 7.07 (d, 8H), 7.00 (t, 4H), 6.53 (s, 1H), 6.28 (dd, 2H)

Preparation Example 7. Synthesis of Intermediate 7 (1-Bromo-3-diphenylamine-5-fluorobenzene)

In a 250 ml round bottom three-necked flask under nitrogen atmosphere, 10.2 g of 1-bromo-3,5-difluorobenzene, 3.4 g of diphenylamine, and 0.4 g of tris(dibenzylideneacetone) were placed. Di-palladium (0), 0.2 g of triphenylphosphine, 5.8 g of sodium t-butoxide and 100 ml of toluene were stirred at 100 ° C for 4 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 4.8 g of Intermediate 7 (yield 70%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 7.31 (t, 4H), 7.12-7.07 (m, 6H), 6.90 (s, 1H), 6.77 (d, 1H), 6.60 (d, 1H)

PREPARATION EXAMPLE 8. Synthesis of Intermediate 8 (9-(3-Bromo-5-diphenylaminophenyl)-3-diphenylamino-9H-indazole)

A 100 ml round bottom three-necked flask under nitrogen atmosphere was charged with 3.4 g of Intermediate 7, 3.3 g of Intermediate 3, 0.8 g of 60% sodium hydride and 50 ml of DMF, and stirred at 110 ° C for 2 hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane. The organic layer was then removed with anhydrous magnesium sulfate and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 4.9 g of Intermediate 8 (yield 75%).

PREPARATION EXAMPLE 9. Synthesis of Intermediate 9 (9-(3-Bromo-5-(9H-carbazolyl)phenyl)-3-diphenylamino-9H-indazole)

A 100 ml round bottom three-necked flask under nitrogen atmosphere was charged with 4.1 g of Intermediate 5, 4.0 g of Intermediate 3, 1.0 g of 60% sodium hydride and 60 ml of DMF, and stirred at 110 ° C for 4 hours. After the completion of the reaction, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane, and then the organic layer was removed from water and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 5.5 g of Intermediate 9 (yield 70%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 8.15 (d, 2H), 7.98 (d, 1H), 7.91 (s, 1H), 7.85 (d, 2H), 7.79 (s, 1H), 7.54-7.52 (m , 3H), 7.48-7.43 (m, 4H), 7.32 (t, 2H), 7.27-7.20 (m, 6H), 7.12 (d, 4H), 6.96 (t, 2H)

Preparation Example 10. Synthesis of Intermediate 10 (3,6-Diphenyl-9H-carbazole)

In a 250 ml round bottom three-necked flask under nitrogen atmosphere, 5.0 g of 3,6-dibromocarbazole, 4.1 g of phenylboronic acid, and 0.4 g of tetrakis(triphenylphosphine)palladium(0) were placed. 5.9 g of sodium t-butoxide and 150 ml of toluene were stirred under reflux for 24 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 3.3 g of Intermediate 10 (yield 68%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 8.33 (s, 2H), 8.11 (s, 1H), 7.72 (d, 4H), 7.69 (d, 2H), 7.51-7.46 (m, 6H), 7.34 (t , 2H)

PREPARATION EXAMPLE 11. Synthesis of Intermediate 11 (9-(3-Bromo-5-fluorophenyl)-3,6-diphenyl-9H-carbazole)

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 5.7 g of 1-bromo-3,5-difluorobenzene, 3.3 g of intermediate 10, 0.8 g of 60% sodium hydride and 50 ml of DMF were placed. It was stirred at 110 ° C for 4 hours. After the reaction is completed, the reaction solution is transferred to a separatory funnel so that the layer is water and dichloride. The methane was separated, and then the organic layer was removed with anhydrous magnesium sulfate and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 3.1 g of Intermediate 11 (yield 62%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 8.39 (s, 2H), 7.75 (d, 4H), 7.70 (d, 2H), 7.60 (s, 1H), 7.55-7.48 (m, 6H), 7.41-7.36 (m, 3H), 7.32 (d, 1H)

PREPARATION EXAMPLE 12. Intermediate 12 (9-(3-Bromo-5-(3,6-diphenyl-9H-carbazolyl)phenyl)-3-diphenylamino-9H-carbazole) Synthesis

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 3.1 g of Intermediate 11, 2.2 g of Intermediate 3, 0.5 g of 60% sodium hydride and 35 ml of DMF were placed, and stirred at 110 ° C for 4 hours. After the completion of the reaction, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane, and then the organic layer was removed from water and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane. There was obtained 5.2 g of Intermediate 12 (yield 67%).

Preparation Example 13. Synthesis of Intermediate 13 (3,6-Dimethyl-9H-carbazole)

In a 1 liter round bottom three-necked flask under nitrogen atmosphere, 16 g of 3,6-dibromocarbazole, 1.4 g of nickel (diphenylphosphinoferrocene) chloride (2) and 600 ml were placed. Diethyl ether and slowly added dropwise 30 ml of 3M magnesium bromide at room temperature. The reaction mixture was refluxed for 8 hours, after which the reaction solution was cooled, washed with aqueous ammonium chloride and neutralized with aqueous sodium carbonate. The organic layer was then dried over magnesium sulfate, filtered and concentrated. The concentrated solution was subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 2.4 g of Intermediate 13 (yield 24%).

¹ H NMR (Acetone, d ₆ , 600 MHz) δ 10.02 (s, 1H), 7.83 (s, 2H), 7.32 (d, 2H), 7.15 (d, 2H), 2.45 (s, 6H)

PREPARATION EXAMPLE 14. Synthesis of Intermediate 14 (9-(3-Bromo-5-fluorophenyl)-3,6-dimethyl-9H-carbazole)

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 5.7 g of 1-bromo-3,5-difluorobenzene, 2.0 g of intermediate 13, 0.8 g of 60% sodium hydride and 50 ml of DMF were placed. It was stirred at 110 ° C for 4 hours. After the completion of the reaction, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane, and then the organic layer was removed from water and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 2.4 g of Intermediate 14 (yield 65%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 7.87 (s, 2H), 7.54 (s, 1H), 7.33 (d, 2H), 7.30 (d, 1H), 7.26 (d, 1H), 7.22 (d, 2H ), 2.53 (s, 6H)

PREPARATION EXAMPLE 15. Intermediate 15 (9-(3-Bromo-5-(3,6-dimethyl-9H-carbazolyl)phenyl)-3-diphenylamino-9H-indazole) Synthesis

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 2.4 g of Intermediate 14, 2.2 g of Intermediate 3, 0.5 g of 60% sodium hydride and 35 ml of DMF were placed, and stirred at 110 ° C for 4 hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane. The organic layer was then removed with anhydrous magnesium sulfate and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus yielding 3.7 g of Intermediate 15 (yield 83%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 7.98 (d, 1H), 7.90 (s, 1H), 7.88 (s, 2H), 7.81 (d, 2H), 7.76 (s, 1H), 7.51 (d, 1H ), 7.46 (d, 1H), 7.43-7.40 (m, 3H), 7.26-7.21 (m, 8H), 7.10 (d, 4H), 6.96 (t, 2H), 2.53 (s, 6H)

PREPARATION EXAMPLE 16. Synthesis of Intermediate 16 (9-(1,3-bis(diphenylamino)phenyl)-3-bromo-9H oxazole)

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 5.5 g of intermediate 6, 3.2 g of 3-bromocarbazole, 1.0 g of 60% sodium hydride and 65 ml of DMF were placed and stirred under reflux 24 hour. After the completion of the reaction, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane, and then the organic layer was removed from water and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 4.0 g of Intermediate 16 (yield 47%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 8.14 (s, 1H), 8.98 (d, 1H), 7.42-7.37 (m, 3H), 7.28-7.22 (m, 10H), 7.15 (d, 8H), 6.99 (t, 4H), 6.87 (s, 1H), 6.70 (s, 2H)

PREPARATION EXAMPLE 17. Synthesis of Intermediate 17 (1-Bromo-(3,5-bisdiphenylamino)benzene)

In a 500 ml round bottom three-necked flask under nitrogen atmosphere, 9.0 g of 1,3,5-tribromobenzene, 8.0 g of diphenylamine, and 0.3 g of tris(dibenzylideneacetone)dipalladium were placed. (0), 0.3 g of triphenylphosphine, 19.4 g of sodium t-butoxide and 200 ml of toluene, and stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 6.3 g of Intermediate 17 (yield 85%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 7.23 (t, 8H), 7.07 (d, 8H), 7.01 (t, 4H), 6.75 (d, 2H), 6.71 (d, 1H)

PREPARATION EXAMPLE 18. Synthesis of Intermediate 18 (4'-Bromo-2-nitro-1,1'-biphenyl)

Put 4.9 into a 250 ml round bottom three-necked flask under nitrogen Grams of 2-iodonitrobenzene, 4.3 grams of 4-bromophenylboronic acid, 0.2 grams of palladium(II) acetate, 0.8 grams of triphenylphosphine, 6.0 grams of potassium carbonate, 20 ml of ethanol, 20 ml of water And 175 ml of toluene and stirred under reflux for 24 hours. The reaction solution was cooled, then extracted with dichloromethane and water, then the organic layer was concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 4.4 g of intermediate 18 (yield 81%) ).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 7.88 (d, 1H), 7.62 (t, 1H), 7.56-7.51 (m, 2H), 7.50 (t, 1H), 7.39 (d, 1H), 7.19-7.17 (m, 2H)

PREPARATION EXAMPLE 19. Synthesis of Intermediate 19 (4'-Diphenylamino-2-nitro-1,1'-biphenyl)

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 4.4 g of intermediate 18, 2.7 g of diphenylamine, 0.5 g of tris(dibenzylideneacetone)dipalladium (0), 0.6 g were placed. 15% tri(tert-butyl)phosphine, 4.6 g of sodium t-butoxide and 80 ml of toluene were stirred at 80 ° C for 12 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 4.9 g of Intermediate 19 (yield 84%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 7.80 (d, 1H), 7.57 (t, 1H), 7.46-7.42 (m, 2H), 7.29-7.26 (m, 4H), 7.17-7.14 (m, 6H) , 7.08-7.04(m,4H)

Preparation Example 20. Synthesis of Intermediate 20 (2-Diphenylamino-9H-carbazole)

In a 100 ml round bottom three-necked flask under a nitrogen atmosphere, 4.9 g of an intermediate 19, 8.8 g of triphenylphosphine and 20 ml of o-dichlorobenzene were placed, and stirred under reflux for 24 hours. The reaction solution was cooled, and then the organic layer was concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thereby obtaining 2.4 g of Intermediate 20 (yield 53%).

¹ H NMR (Acetone, d ₆ , 600 MHz) δ 10.15 (s, 1H), 8.02 (d, 1H), 7.99 (d, 1H), 7.43 (d, 1H), 7.30 (t, 1H), 7.28-7.25 (m, 4H), 7.13 (t, 2H), 7.07 (d, 4H), 7.00 (t, 2H), 6.91 (d, 1H)

Preparation Example 21. Synthesis of Intermediate 21 (2'-Diphenylamino-2-nitro-1,1'-biphenyl)

Place 6.2 in a 500 ml round bottom three-necked flask under nitrogen atmosphere. Grams of 2-iodonitrobenzene, 5.5 grams of 2-bromophenylboronic acid, 0.3 grams of palladium(II) acetate, 1.0 grams of triphenylphosphine, 7.6 grams of potassium carbonate, 25 ml of ethanol, 25 ml of water And 200 ml of toluene and stirred under reflux for 24 hours. The reaction solution was cooled, then extracted with dichloromethane and water, and then the organic layer was concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 5.0 g of intermediate 21 (yield 72%) ).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 8.12 (d, 1H), 7.69 (t, 1H), 7.65 (d, 1H), 7.60 (d, 1H), 7.38 (t, 1H), 7.37 (d, 1H ), 7.31-7.25 (m, 2H)

PREPARATION EXAMPLE 22. Synthesis of Intermediate 22 (2'-Diphenylamino-2-nitro-1,1'-biphenyl)

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 5.0 g of intermediate 21, 3.0 g of diphenylamine, 0.5 g of tris(dibenzylideneacetone)dipalladium (0), 0.6 g were placed. 15% tri(tert-butyl)phosphine, 5.2 g of sodium t-butoxide and 90 ml of toluene were stirred at 80 ° C for 12 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 5.1 g of Intermediate 22 (yield 77%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 7.69 (d, 1H), 7.34 (t, 1H), 7.27-7.22 (m, 4H), 7.18 (t, 1H), 7.02 (t, 4H), 6.91 (d ,1H), 6.83(t,2H),6.76(d,4H)

Preparation Example 23. Synthesis of Intermediate 23 (4-Diphenylamino-9H-carbazole)

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 5.1 g of Intermediate 22, 9.2 g of triphenylphosphine and 25 ml of o-dichlorobenzene were placed, and stirred under reflux for 24 hours. The reaction solution was cooled, and then the organic layer was concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 2.9 g of Intermediate 23 (yield 62%).

¹ H NMR (Acetone, d ₆ , 600 MHz) δ 10.53 (s, 1H), 7.69 (d, 1H), 7.99 (d, 1H), 7.46-7.43 (m, 2H), 7.40 (t, 1H), 7.27 (t, 1H), 7.21-7.18 (m, 4H), 7.03 (d, 4H), 6.90 (t, 2H), 6.86 (d, 1H)

Preparation Example 24. Synthesis of Intermediate 24 (9-(1,3-Dibromophenyl)-3-bromo-9H-indazole)

In a 250 ml round bottom three-necked flask under nitrogen atmosphere, 6.0 g of 1,3-dibromo-5-fluorobenzene, 5.8 g of 3-bromocarbazole, 1.9 g of 60% sodium hydride and 120 ml were placed. DMF and stirred at 160 ° C for 12 hours. After the completion of the reaction, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane, and then the organic layer was removed from water and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 8.0 g of Intermediate 24 (yield 71%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 8.23 (s, 1H), 8.06 (d, 1H), 7.78 (s, 1H), 7.65 (s, 1H), 7.64 (s, 1H), 7.51 (d, 1H) ), 7.46 (t, 1H), 7.39 (d, 1H), 7.32 (d, 1H), 7.27 (d, 1H)

Preparation Example 25. Synthesis of Intermediate 25 (9-(1,3-Dibromophenyl)-4-bromo-9H-indazole)

In a 250 ml round bottom three-necked flask under nitrogen atmosphere, 6.0 g of 1,3-dibromo-3-fluorobenzene, 5.8 g of 4-bromocarbazole, 1.9 g of 60% sodium hydride and 120 ml were placed. DMF and stir at 160 ° C for 24 hours. After the completion of the reaction, the reaction solution was transferred to a separatory funnel so that the layer was separated from water and dichloromethane, and then the organic layer was removed from water and filtered. The filtrate was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 7.3 g of Intermediate 25 (yield 65%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 8.83 (s, 1H), 7.80 (s, 1H), 7.65 (s, 1H), 7.64 (s, 1H), 7.50-7.47 (m, 2H), 7.38-7.35 (m, 2H), 7.31 (d, 1H), 7.27 (d, 1H)

Example 1. Synthesis of Compound 1

A 100 ml round bottom three-necked flask under nitrogen atmosphere was charged with 3.3 g of the intermediate 4 synthesized in Preparation Example 4, 3.4 g of diphenylamine, and 0.3 g of tris(dibenzylideneacetone)dipalladium ( 0), 0.4 g of 15% tris(tert-butyl)phosphine, 5.8 g of sodium t-butoxide and 50 ml of toluene, and stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 6.3 g of Compound 1 (yield 85%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 7.88 (d, 1H), 7.81 (s, 1H), 7.35 (d, 1H), 7.34-7.32 (m, 2H), 7.25-7.14 (m, 22H), 7.07 (d, 4H), 6.98 (t, 4H), 6.93 (t, 2H), 6.86 (t, 1H), 6.77 (d, 2H)

MS (ESI): [M+H] ⁺ 745

Tg: 111 ° C

Tm: 267 ° C

Example 2. Synthesis of Compound 2

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 3.3 g of the intermediate synthesized in Preparation Example 8, 8, 1.0 g of di-p-tolylamine, 0.1 g of tris(dibenzylideneacetone) were placed. Di-palladium (0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.4 g of sodium t-butoxide and 50 ml of toluene were stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 3.3 g of Compound 2 (yield 85%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) 7.88 (d, 1H), 7.81 (s, 1H), 7.38 (d, 1H), 7.35-7.31 (m, 2H), 7.25-7.13 (m, 14H), 7.07 ( d, 4H), 7.05-7.00 (m, 8H), 6.98 (t, 2H), 6.94 (t, 2H), 6.82 (s, 1H), 6.72 (d, 2H)

MS (ESI): [M+H] ⁺ 773

Example 3. Synthesis of Compound 5

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 3.0 g of the intermediate 9 synthesized in Preparation Example 9 was placed, and the reaction solution was cooled, filtered with a silica gel, concentrated, and then a solvent of dichloromethane and n-hexane was used. The mixture was subjected to column chromatography to give 3.1 g of Compound 5 (yield: 92%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 8.10 (d, 2H), 7.94 (d, 1H), 7.86 (s, 1H), 7.53-7.50 (m, 3H), 7.46 (d, 1H), 7.42-7.37 (m, 4H), 7.36-7.26 (m, 12H), 7.24-7.19 (m, 6H), 7.07-7.08 (m, 6H), 6.95 (t, 2H)

MS (ESI): [M+H] ⁺ 743

Tg: 133 ° C

Example 4. Synthesis of Compound 6

A 100 ml round bottom three-necked flask under nitrogen atmosphere was charged with 4.0 g of the intermediate 12 synthesized in Preparation Example 12, 1.0 g of diphenylamine, and 0.1 g of tris(dibenzylideneacetone)dipalladium ( 0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.4 g of sodium t-butoxide and 50 ml of toluene, and stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 4.0 g of Compound 6 (yield 90%).

¹ H NMR (CDCl ₃ , 600 MHz) 8.36 (s, 2H), 7.95 (d, 1H), 7.78 (s, 1H), 7.71 (d, 4H), 7.67 (dd, 2H), 7.60 (d, 2H) , 7.54 (d, 1H), 7.48-7.46 (m, 5H), 7.43-7.31 (m, 12H), 7.31 (s, 2H), 7.25-7.20 (m, 6H), 7.12-7.06 (m, 6H) , 6.95(t, 2H)

MS (ESI): [M+H] ⁺ 895

Example 5. Synthesis of Compound 7

A 100 ml round bottom three-necked flask under nitrogen atmosphere was charged with 3.4 g of the intermediate 15 synthesized in Preparation Example 15, 0.8 g of diphenylamine, and 0.1 g of tris(dibenzylideneacetone)dipalladium ( 0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.4 g of sodium t-butoxide and 50 ml of toluene, and stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, whereby 3.4 g of Compound 7 (yield 88%) was obtained.

¹ H NMR (CDCl ₃ , 600 MHz) δ 7.94 (d, 1H), 7.87 (s, 1H), 7.85 (s, 2H), 7.51 (d, 1H), 7.46 (d, 1H), 7.41-7.30 (m) , 13H), 7.23-7.19 (m, 9H), 7.10-7.08 (m, 6H), 6.95 (t, 2H), 2.51 (s, 6H)

MS (ESI): [M+H] ⁺ 771

Example 6. Synthesis of Compound 8

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 3.1 g of the intermediate synthesized in Preparation Example 8, 8, 1.0 g of 9,9-dimethyl-9,10-dihydroacridine, 0.1 g were placed. Tris(dibenzylideneacetone)dipalladium (0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.4 g of sodium t-butoxide and 50 ml of toluene were stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, whereby 3.1 g of Compound 8 (yield 80%) was obtained.

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 7.92 (d, 1H), 7.85 (s, 1H), 7.46 (d, 1H), 7.43-7.40 (m, 3H), 7.38-7.29 (m, 6H), 7.26 -7.24(m,4H),7.22-7.18(m,6H),7.12-7.04(m,10H),6.94(t,4H),6.56(d,2H)

MS (ESI): [M+H] ⁺ 785

Example 7. Synthesis of Compound 12

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 2.5 g of the intermediate 9 synthesized in Preparation Example 9, 0.8 g of di-p-tolylamine, and 0.1 g of tris(dibenzylideneacetone) were placed. Di-palladium (0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.1 g of sodium t-butoxide and 50 ml of toluene were stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus yielding 2.6 g of Compound 12 (yield 90%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 8.11 (d, 2H), 7.95 (d, 1H), 7.78 (s, 1H), 7.53-7.50 (m, 3H), 7.46 (d, 1H), 7.43-7.36 (m, 3H), 7.28-7.19 (m, 15H), 7.13 (d, 4H), 7.11 (d, 4H), 6.96 (t, 2H), 2.30 (s, 6H)

MS (ESI): [M+H] ⁺ 771

Tg: 134 ° C

Example 8. Synthesis of Compound 19

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 3.1 g of the intermediate 16 synthesized in Preparation Example 16 and 1.0 g of 9,9-dimethyl-9,10-dihydroacridine, 0.1 g were placed. Tris(dibenzylideneacetone)dipalladium (0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.4 g of sodium t-butoxide and 50 ml of toluene were stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus yielding 3.1 g of Compound 19 (yield 85%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 8.00 (s, 1H), 7.97 (d, 1H), 7.60 (d, 1H), 7.47-7.44 (m, 3H), 7.41 (t, 1H), 7.27-7.21 (m, 10H), 7.18 (d, 8H), 7.00 (t, 4H), 6.91-6.88 (m, 5H), 6.84 (d, 2H), 6.28-6.27 (m, 2H), 1.72 (s, 6H) )

MS (ESI): [M+H] ⁺ 785

Tg: 122 ° C

Example 9. Synthesis of Compound 47

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 4.9 g of the intermediate 17 synthesized in Preparation Example 17, 0.5 g of aniline, 0.3 g of tris(dibenzylideneacetone) dipalladium (0), 0.4 g of 15% tri(tert-butyl)phosphine, 2.9 g of sodium t-butoxide and 50 ml of toluene were stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, whereby 4.3 g of Compound 47 (yield 93%) was obtained.

¹ H NMR (CDCl ₃ , 600 MHz) δ 7.16 (t, 16H), 7.05 (t, 2H), 6.98 (d, 16H), 6.95-6.90 (m, 10H), 6.78 (t, 1H), 6.37-6. (m, 6H)

MS (ESI): [M+H] ⁺ 914

Example 10. Synthesis of Compound 31

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 1.8 g of the intermediate 17 synthesized in Preparation Example 17, 1.2 g of the intermediate synthesized in Preparation Example 20, and 0.1 g of tris(dibenzylidene) were placed. Acetone) dipalladium (0), 0.1 g of 15% tris(tert-butyl)phosphine, 1.0 g of sodium t-butoxide and 20 ml of toluene were stirred at 80 ° C for 3 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to afford 2.1 g of Compound 31 (yield 79%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 7.94 (d, 1H), 7.89 (d, 1H), 7.31-7.27 (m, 2H), 7.23-7.15 (m, 14H), 7.08-7.06 (m, 12H) , 6.99-6.94 (m, 7H), 6.76 (s, 1H), 6.65 (s, 2H)

MS (ESI): [M+H] ⁺ 745

Example 11. Synthesis of Compound 34

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 2.4 g of the intermediate 17 synthesized in Preparation Example 17, 1.6 g of the intermediate synthesized in Preparation Example 23, and 0.1 g of tris(dibenzylidene) were placed. Acetone) dipalladium (0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.4 g of sodium t-butoxide and 25 ml of toluene were stirred at 80 ° C for 3 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to obtain 2.9 g of Compound 34 (yield 81%).

¹ H NMR (CDCl ₃ , 600 MHz) δ 7.69 (d, 1H), 7.32 (t, 2H), 7.29 (d, 1H), 7.27-7.23 (m, 10H), 7.17-7.14 (m, 12H), 7.07 (d, 4H), 6.99 (t, 4H), 6.94-6.88 (m, 4H), 6.80 (d, 2H)

MS (ESI): [M+H] ⁺ 745

Example 12. Synthesis of Compound 64

Put in a 100 ml round bottom three-necked flask under nitrogen atmosphere. The intermediate synthesized in Preparation Example 24, 3.0 g of bisbenzidine, 0.2 g of tris(dibenzylideneacetone)dipalladium (0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.4 Gram of sodium t-butoxide and 20 ml of toluene were stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane to afford 3.0 g of Compound 64 (yield 79%).

_{^{1 H NMR (CDCl 3, 600MHz}} ) δ 7.95 (s, 1H), 7.92 (d, 1H), 7.56 (d, 4H), 7.51-7.45 (m, 22H), 7.42-7.39 (m, 5H), 7.36 (t,8H),7.31-7.25(m,15H),7.19-7.18(m,5H),6.98(s,1H),6.96(s,2H)

MS (ESI): [M+H] ⁺ 1202

Example 13. Synthesis of Compound 65

In a 100 ml round bottom three-necked flask under nitrogen atmosphere, 1.5 g of the intermediate synthesized in Preparation Example 25, 3.0 g of bisbenzidine, 0.2 were placed. Glucose tris(dibenzylideneacetone)dipalladium (0), 0.2 g of 15% tris(tert-butyl)phosphine, 1.4 g of sodium t-butoxide and 20 ml of toluene were stirred at 80 ° C for 2 hours. The reaction solution was cooled, filtered with hydrazine, concentrated, and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, whereby 3.2 g of Compound 65 (yield 85%) was obtained.

¹ H NMR (CDCl ₃ , 600 MHz) δ 7.80 (d, 1H), 7.53-7.50 (m, 20H), 7.45-7.41 (m, 7H), 7.38-7.35 (m, 12H), 7.32-7.29 (m, 13H), 7.27-7.24 (m, 3H), 7.19 (d, 4H), 7.05 (d, 1H), 7.00 (s, 1H), 6.98 (s, 2H)

MS (ESI): [M+H] ⁺ 1202

Apparatus Example 1. Manufacturing of an organic EL device including Compound 1 as a hole transport layer

A glass substrate coated with a 100 nm thick ITO (indium tin oxide) film was ultrasonically washed, dried, and placed in a plasma cleaning system using an isopropyl alcohol solvent, so that the substrate was washed with oxygen plasma for 5 minutes. It is then transferred into the vacuum deposition system.

The prepared ITO transparent electrode was thus used as an anode, and DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolylamino)-phenyl ]-biphenyl-4,4'-diamine] was vacuum deposited on an ITO substrate, thereby forming a hole injection layer having a thickness of 55 nm. Thereafter, Compound 1 having a thickness of 30 nm was vacuum-deposited, thereby forming a hole transport layer, and CBP [4,4-N,N-dicarbazolebiphenyl] having a thickness of 25 nm was vacuum-deposited on the hole transport layer as a host and 6 vol% of Ir(PPy) ₃ [tris(2-phenylpyridine) fluorene] was used as a dopant, thereby forming a light-emitting layer.

After that, Bphen[4,7-diphenyl-1,10-morpholine] is used in the luminescent layer. An electron transport layer having a thickness of 30 nm was formed thereon. 2 nm thick Liq (lithium quinoline salt) and 100 nm thick Al were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby fabricating an organic EL device.

Apparatus Example 2. Manufacturing of an organic EL device including Compound 5 as a hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 1, except that Compound 5 was used instead of Compound 1.

Device Example 3. Manufacturing of an organic EL device including Compound 12 as a hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 1, except that Compound 12 was used instead of Compound 1.

Apparatus Example 4. Manufacturing of an organic EL device including Compound 19 as a hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 1, except that Compound 19 was used instead of Compound 1.

Apparatus Example 5. Manufacturing of an organic EL device including Compound 34 as a hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 1, except that Compound 34 was used instead of Compound 1.

Apparatus Example 6. Manufacturing of an organic EL device including Compound 47 as a hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 1, except that Compound 47 was used instead of Compound 1.

Apparatus Example 7. Manufacturing including Compound 64 as a hole transport layer Organic EL device

An organic EL device was fabricated in the same manner as in Device Example 1, except that Compound 64 was used instead of Compound 1.

Apparatus Example 8. Manufacturing of an organic EL device including Compound 65 as a hole transport layer

An organic EL device was manufactured in the same manner as in Device Example 1, except that Compound 65 was used instead of Compound 1.

Comparative Apparatus Example 1. Manufacturing of an organic EL device including NPB as a hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 1, except that NPB was used instead of Compound 1.

Apparatus Example 9. Manufacturing of an organic EL device including Compound 1 as a second hole transport layer

A glass substrate coated with an ITO film having a thickness of 100 nm was ultrasonically washed, dried, and placed in a plasma cleaning system using an isopropyl alcohol solvent, so that the substrate was washed with oxygen plasma for 5 minutes and then transferred to a vacuum. Deposition system.

The prepared ITO transparent electrode was thus used as an anode, and DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolylamino)-phenyl ]-biphenyl-4,4'-diamine] was vacuum deposited on an ITO substrate, thereby forming a hole injection layer having a thickness of 55 nm. Thereafter, NPB[N,N'-bis(naphthalen-1-yl)-N,N'-diphenyl-benzidine] having a thickness of 20 nm was vacuum-deposited, thereby forming a first hole transport layer, and using Compound 1 at A second hole transport layer having a thickness of 10 nm is formed on the first hole transport layer. Vacuum deposition of 25 nm thick CBP[4,4-N,N-dicarbazolebiphenyl] as the host and 6 vol% of Ir(PPy) ₃ [tris(2-benzene) on the second hole transport layer As a dopant, a pyridyl layer is formed as a dopant.

Thereafter, an electron transport layer having a thickness of 30 nm was formed on the light-emitting layer using Bphen [4,7-diphenyl-1,10-morpholine]. 2 nm thick Liq (lithium quinoline salt) and 100 nm thick Al were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby fabricating an organic EL device.

Device Example 10. Manufacturing of an organic EL device including Compound 5 as a second hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 9, except that Compound 5 was used instead of Compound 1.

Apparatus Example 11. Manufacturing of an organic EL device including Compound 12 as a second hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 9, except that Compound 12 was used instead of Compound 1.

Apparatus Example 12. Manufacturing of an Organic EL Device Comprising Compound 19 as a Second Hole Transport Layer

An organic EL device was fabricated in the same manner as in Device Example 9, except that Compound 19 was used instead of Compound 1.

Device Example 13. Fabrication of an Organic EL Device Comprising Compound 34 as a Second Hole Transport Layer

An organic EL device was fabricated in the same manner as in Device Example 9, except that Compound 34 was used instead of Compound 1.

Apparatus Example 14. Production of an Organic EL Device Comprising Compound 47 as a Second Hole Transport Layer

An organic EL device was fabricated in the same manner as in Device Example 9, except that Compound 47 was used instead of Compound 1.

Apparatus Example 15. Manufacturing of an Organic EL Device Comprising Compound 64 as a Second Hole Transport Layer

An organic EL device was fabricated in the same manner as in Device Example 9, except that Compound 64 was used instead of Compound 1.

Apparatus Example 16. Manufacturing of an Organic EL Device Comprising Compound 65 as a Second Hole Transport Layer

An organic EL device was fabricated in the same manner as in Device Example 9, except that Compound 65 was used instead of Compound 1.

Comparative device example 2. Manufacturing of an organic EL device including NPB as a second hole transport layer

An organic EL device was fabricated in the same manner as in Device Example 9, except that NPB was used instead of Compound 1.

The chemical formulas of DNTPD, NPB, CBP, and Bphen used in the examples are shown below.

Test example: Evaluating the properties of organic EL devices

The device properties of Device Examples 1 to 14 and Comparative Device Examples 1 to 2 were evaluated at a luminance of 1000 cd/m ² , and the results are shown in Table 1 and Table 2 below.

Current density

In the manufactured organic EL device, when the voltage is increased from 0 volt (V) to 10 V, the current of each unit device is measured using a current-voltage meter (Keithley 2635A Source Meter), and the measured current value is divided. The current density is obtained by the area.

Brightness efficiency

In the manufactured organic EL device, when the voltage was increased from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta CS-2000), and the measured luminance value was divided by the current value to obtain luminance efficiency.

Color coordinates

Color coordinates were measured using a luminance meter (Minolta CS-2000).

From the results of manufacturing an organic EL device using the compound according to the present invention as a material of a hole transport layer or a second hole transport layer, it is apparent that all devices exhibit superiority as compared with the case of using NPB as a conventional material. The nature.

Although the preferred embodiment of the present invention has been disclosed for purposes of illustration, it will be understood by those of ordinary skill in the art repair It is possible to change, add and replace.

1‧‧‧Organic EL device

110‧‧‧First electrode

130‧‧‧Organic layer

150‧‧‧second electrode

Claims (11)

A compound for an organic electroluminescent device is represented by the following Chemical Formula 1: Wherein Ar ¹ to Ar ⁴ are the same or different from each other, and each of Ar ¹ to Ar ^{4 is} independently a substituted or unsubstituted C 1 to C 30 alkyl group, a monosubstituted or unsubstituted C 3 to C 30 cycloalkyl group, a monosubstituted group. Or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 aryl, or monosubstituted or unsubstituted C1 to C30 heteroaryl, or Ar ¹ and Ar ² and Ar ³ and Ar ^{4 is} bonded to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group, respectively, having an intermediate nitrogen atom, and R ¹ is a hydrogen atom, Monosubstituted or unsubstituted C1 to C30 alkyl, monosubstituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 To a C30 aryl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group, R ² to R ⁵ are the same or different from each other, and R ² to R ⁵ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl, monosubstituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 An aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R ² to R ⁵ is further coupled to a carbon atom adjacent to a carbon atom to which it is attached to form a substituted or Unsubstituted fused C3 to C30 cycloalkyl, monosubstituted or unsubstituted fused C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted fused C6 to C30 aryl, or monosubstituted or unsubstituted Substituted fused C1 to C30 heteroaryl, X and Y are the same or different from each other, and X and Y are each independently a monovalent bond or Wherein Z is a carbon atom or a fluorene atom, and R ⁶ and R ⁷ are the same or different from each other, and R ⁶ and R ⁷ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl group, Substituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 aryl, or monosubstituted or unsubstituted C1 To C30 heteroaryl, q is 0 or 1, m is 0 or 1, n is 0 or 1, and m+n≠0. The compound according to claim 1, which is represented by any one of the following Chemical Formulas 2 and 3: [Chemical Formula 2] Wherein Ar ¹ to Ar ⁴ are the same or different from each other, and each of Ar ¹ to Ar ^{4 is} independently a substituted or unsubstituted C 1 to C 30 alkyl group, a monosubstituted or unsubstituted C 3 to C 30 cycloalkyl group, a monosubstituted group. Or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 aryl, or monosubstituted or unsubstituted C1 to C30 heteroaryl, or Ar ¹ and Ar ² and Ar ³ and Ar ^{4 is} bonded to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group, respectively, having an intermediate nitrogen atom, and R ¹ is a hydrogen atom, Monosubstituted or unsubstituted C1 to C30 alkyl, monosubstituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 To a C30 aryl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group, R ² to R ⁵ are the same or different from each other, and R ² to R ⁵ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl, monosubstituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C3 The 0 aryl group, or the monosubstituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R ² to R ⁵ is further coupled to a carbon atom adjacent to a carbon atom to which it is linked to form a substituted Or unsubstituted fused C3 to C30 cycloalkyl, monosubstituted or unsubstituted fused C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted fused C6 to C30 aryl, or monosubstituted or Unsubstituted fused C1 to C30 heteroaryl, and X and Y are the same or different from each other, and X and Y are each independently a monovalent bond or Wherein Z is a carbon atom or a fluorene atom, and R ⁶ and R ⁷ are the same or different from each other, and R ⁶ and R ⁷ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl group, Substituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 aryl, or monosubstituted or unsubstituted C1 To C30 heteroaryl. The compound according to claim 1, which is represented by any one of the following Chemical Formulas 4 and 5: [Chemical Formula 4] Wherein Ar ¹ to Ar ⁴ are the same or different from each other, and each of Ar ¹ to Ar ^{4 is} independently a substituted or unsubstituted C 1 to C 30 alkyl group, a monosubstituted or unsubstituted C 3 to C 30 cycloalkyl group, a monosubstituted group. Or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 aryl, or monosubstituted or unsubstituted C1 to C30 heteroaryl, or Ar ¹ and Ar ² and Ar ³ and Ar ^{4 is} bonded to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group, respectively, having an intermediate nitrogen atom, and R ¹ is a hydrogen atom, Monosubstituted or unsubstituted C1 to C30 alkyl, monosubstituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 To a C30 aryl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group, R ² to R ⁵ are the same or different from each other, and R ² to R ⁵ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl, monosubstituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C3 The 0 aryl group, or the monosubstituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R ² to R ⁵ is further coupled to a carbon atom adjacent to a carbon atom to which it is linked to form a substituted Or unsubstituted fused C3 to C30 cycloalkyl, monosubstituted or unsubstituted fused C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted fused C6 to C30 aryl, or monosubstituted or Unsubstituted fused C1 to C30 heteroaryl, and X and Y are the same or different from each other, and X and Y are each independently a monovalent bond or Wherein Z is a carbon atom or a fluorene atom, and R ⁶ and R ⁷ are the same or different from each other, and R ⁶ and R ⁷ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl group, Substituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 aryl, or monosubstituted or unsubstituted C1 To C30 heteroaryl. The compound according to claim 1, which is represented by any one of the following Chemical Formulas 6 and 7: [Chemical Formula 6] Wherein Ar ¹ to Ar ⁴ are the same or different from each other, and each of Ar ¹ to Ar ^{4 is} independently a substituted or unsubstituted C 1 to C 30 alkyl group, a monosubstituted or unsubstituted C 3 to C 30 cycloalkyl group, a monosubstituted group. Or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 aryl, or monosubstituted or unsubstituted C1 to C30 heteroaryl, or Ar ¹ and Ar ² and Ar ³ and Ar ^{4 is} bonded to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group, respectively, having an intermediate nitrogen atom, and R ¹ is a hydrogen atom, Monosubstituted or unsubstituted C1 to C30 alkyl, monosubstituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 To a C30 aryl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group, R ² to R ⁵ are the same or different from each other, and R ² to R ⁵ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl, monosubstituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 An aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R ² to R ⁵ is further coupled to a carbon atom adjacent to a carbon atom to which it is attached to form a substituted or Unsubstituted fused C3 to C30 cycloalkyl, monosubstituted or unsubstituted fused C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted fused C6 to C30 aryl, or monosubstituted or unsubstituted Substituted fused C1 to C30 heteroaryl, and X and Y are the same or different from each other, and X and Y are each independently a monovalent bond or Wherein Z is a carbon atom or a fluorene atom, and R ⁶ and R ⁷ are the same or different from each other, and R ⁶ and R ⁷ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl group, Substituted or unsubstituted C3 to C30 cycloalkyl, monosubstituted or unsubstituted C1 to C30 heterocycloalkyl, monosubstituted or unsubstituted C6 to C30 aryl, or monosubstituted or unsubstituted C1 To C30 heteroaryl. The compound according to claim 1, wherein Ar ¹ to Ar ⁴ are the same or different from each other, and Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted C1 to C30 alkyl group, a monosubstituted or unsubstituted C3 to C30 cycloalkyl group, or a monosubstituted or unsubstituted C1 to C30 heterocycloalkyl group, or Ar ¹ and Ar ² and Ar ³ and Ar ⁴ are respectively linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group having an intermediate nitrogen atom together, wherein R ^{8 is} R ¹³ are the same or different from each other, and R ⁸ to R ¹³ are each independently a hydrogen atom, a monosubstituted or unsubstituted C1 to C30 alkyl group, a monosubstituted or unsubstituted C3 to C30 cycloalkyl group, a monosubstituted group. Or an unsubstituted C1 to C30 heterocycloalkyl group, a monosubstituted or unsubstituted C6 to C30 aryl group, or a monosubstituted or unsubstituted C1 to C30 heteroaryl group. The compound according to claim 1, which is selected from any one of the compounds 1 to 65 represented by the following chemical formula: An organic electroluminescent device comprising the compound of claim 1. An organic electroluminescent device comprising a first electrode, a second electrode and a single organic layer or a plurality of organic layers interposed between the first electrode and the second electrode, wherein one or more selected from the group consisting of The single organic layer or the organic layer of the plural organic layer includes the compound of claim 1. The organic electroluminescent device of claim 8, wherein the single organic layer or the plurality of organic layers comprises a light-emitting layer. The organic electroluminescent device of claim 8, wherein the plurality of organic layers comprise a light emitting layer, and the plurality of organic layers further comprises an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron One or more of a barrier layer, a hole transport layer, and a hole injection layer. The organic electroluminescent device of claim 9, wherein the luminescent layer comprises a body and a dopant.