KR20080016005A - New anthracene derivatives and organic electronic device using the same - Google Patents

Abstract

An anthracene derivative is provided to exhibit effects such as efficiency increase, driving voltage lowering, and stability rise of an organic electronic device when used a material of an organic material layer. An anthracene derivative has a structure represented by the following formula 1, wherein R1 and R2 are identical to or different from each other and are selected from the group consisting of substituted or unsubstituted C6-40 aryl groups, substituted or unsubstituted C3-40 heteroaryl groups, and substituted or unsubstituted C6-40 amine groups, and at least one of R3 and R4 is a group of the following formula 2 or a group of the following formula 3.

Description

Novel Anthracene Derivatives and Organic Electronic Devices Using Them {NEW ANTHRACENE DERIVATIVES AND ORGANIC ELECTRONIC DEVICE USING THE SAME}

1 illustrates an example of an organic light emitting device according to the present invention.

[Description of Symbols for Main Parts of Drawing]

1. Substrate 2. Anode

3. Hole injection layer 4. Hole transport layer

5. organic light emitting layer 6. electron transport layer

7. Cathode

2 is an MS graph of a compound represented by Chemical Formula 1-1 of the present invention.

3 is an MS graph of a compound represented by Chemical Formula 1-51 of the present invention.

4 is an MS graph of a compound represented by Chemical Formula 1-151 of the present invention.

5 is an MS graph of a compound represented by Formula 2-201 of the present invention.

The present invention relates to a novel anthracene derivative in which a triazole group is bonded to anthracene, and an organic electronic device using the same.

In the present specification, an organic electronic device is an electronic device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and an organic semiconductor material. The organic electronic device can be divided into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form. The second type is an electronic device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.

Examples of organic electronic devices include organic light emitting devices, organic solar cells, organic photoconductor (OPC) drums and organic transistors, all of which are electron / hole injection materials, electron / hole extraction materials, and electron / hole transport materials for driving the devices. Materials or luminescent materials are required. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, an electron / hole injection material, an electron / hole extraction material, an electron / hole transport material, or a light emitting material all operate on a similar principle.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. In this case, the organic material layer is often formed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. . When the voltage is applied between the two electrodes in the structure of the organic light emitting diode, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet, and the excitons are at the bottom. When it falls to the state, it becomes light. Such organic light emitting diodes are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions. The luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order to fully exhibit the excellent characteristics of the organic light emitting device described above, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic layer material for an organic light emitting device has not been sufficiently achieved, and therefore, the development of new materials is still required.

The inventors have discovered an anthracene derivative having a novel structure in which a triazole group is introduced into anthracene. In addition, it has been found that the formation of an organic material layer of an organic electronic device using the novel anthracene derivative may have effects such as an increase in efficiency of the device, a decrease in driving voltage, and an increase in stability.

Accordingly, an object of the present invention is to provide a novel anthracene derivative coupled to triazole and an organic electronic device using the same.

The present invention provides a compound of Formula 1 below.

In Chemical Formula 1,

R1 and R2 are the same as or different from each other, independently halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ alkoxy group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ of, C ₃ Unsubstituted or substituted with one or more groups selected from the group consisting of -C ₄₀ cycloalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, C ₆ -C ₄₀ aryl group, C ₃ -C ₄₀ heteroaryl group, and arylamine group An aryl group of C ₆ to C ₄₀ ; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C _It is selected from the group consisting of C ₆ ~ C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group,

At least one of R3 and R4 is a group of formula (2) or a group of formula (3),

In Chemical Formula 2,

L 1 is a direct bond; An alkoxy group of C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C ₂ -C ₄₀ alkynyl group, C ₁ -C ₄₀ of the, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ C ₂ ~ C ₄₀ alkenylene group unsubstituted or substituted with one or more groups selected from the group consisting of a heteroaryl group of; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C _It is selected from the group consisting of C ₆ ~ C ₄₀ arylamine group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group,

R5 and R6 are the same as or different from each other, and hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted cycloalkyl group of C ₃ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an alkoxy group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or selected from the group consisting of a heteroaryl unsubstituted C ₃ ~ C ₄₀ of ,

In Chemical Formula 3,

L 2 is a direct bond; A C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, a C ₂ -C ₄₀ alkynyl group of, C ₁ -C ₄₀ alkoxy group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ C ₂ -C ₄₀ alkenylene group unsubstituted or substituted with one or more groups selected from the group consisting of a heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C _It is selected from the group consisting of C ₆ ~ C ₄₀ arylamine group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group,

R7 and R8 are the same as or different from each other, hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted cycloalkyl group of C ₃ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an alkoxy group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or is selected from the group consisting of a heteroaryl unsubstituted C ₃ ~ C ₄₀ ,

When group or a date of formula (3) in one of R3 and R4 is the formula (2), the other is halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ A group consisting of a -C ₄₀ alkoxy group, C ₃ -C ₄₀ cycloalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, C ₆ -C ₄₀ aryl group, C ₃ -C ₄₀ heteroaryl group and arylamine group C ₆ ~ C ₄₀ aryl group unsubstituted or substituted with one or more groups selected from; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C _It may be selected from the group consisting of C ₆ ~ C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group have.

In one embodiment of the present invention, R1 and R2 of Formula 1 may be the same aryl group. This aryl group is preferably a substituted or unsubstituted phenyl group, biphenyl group or naphthyl group.

In another exemplary embodiment of the present invention, R1 and R2 of Formula 1 may be the same heteroaryl group. This heteroaryl group is preferably a substituted or unsubstituted pyridyl group, bipyridyl group, quinolyl group or isoquinolyl group.

In another exemplary embodiment of the present invention, R1 and R2 of Chemical Formula 1 may be amino groups substituted with the same C ₆ to C ₄₀ aryl group or C ₃ to C ₄₀ heteroaryl group.

In another exemplary embodiment of the present invention, R1 and R2 of Chemical Formula 1 may be specifically selected from the group consisting of the following structural formulas.

Z1 to Z3 in the structural formula may be the same as or different from each other, and may be independently selected from the groups defined for R1 and R2 of the formula (1).

In another embodiment of the present invention, in the general formula 2, L1 is a direct bond; Unsubstituted C ₆ ~ C ₄₀ arylene group; Or an unsubstituted C ₅ to C ₄₀ heteroarylene group, and at least one of R 5 and R 6 is C ₆ to C ₄₀ unsubstituted or substituted with an alkyl group of C ₁ to C ₄₀ or an aryl group of C ₆ to C ₄₀ An aryl group is preferable.

In another embodiment of the present invention, in the general formula 3, L2 is a direct bond; Unsubstituted C ₆ ~ C ₄₀ arylene group; Or an unsubstituted C ₅ to C ₄₀ heteroarylene group, and one of R 7 and R 8 is C ₆ to C ₄₀ unsubstituted or substituted with an alkyl group of C ₁ to C ₄₀ or an aryl group of C ₆ to C ₄₀ An aryl group is preferable.

Specifically, each substituent will be described as follows.

It is preferable that the alkyl group does not cause steric hindrance of 1 to 40 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, and the like.

It is preferable that a cycloalkyl group does not give a steric hindrance of 3 to 40 carbon atoms. As a specific example, a cyclopentyl group or a cyclohexyl group is more preferable.

As the alkenyl group, an alkenyl group having 2 to 40 carbon atoms is preferable, and an alkenyl group in which aryl groups such as stylbenyl and styrenyl are substituted is particularly preferable.

It is preferable that an alkoxy group is a C1-C40 alkoxy group.

Examples of the aryl group include, but are not limited to, phenyl group, naphthyl group, anthracenyl group, biphenyl group, pyrenyl group, perylene group, derivatives thereof, and the like.

Examples of aryl amine groups include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenyl Amine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole, triphenyl amine group and the like. It is not limited to these.

Examples of the heterocyclic group include pyridyl group, bipyridyl group, triazine group, acridil group, thiopene group, furan group, imidazole group, oxazole group, thiazole group, triazole group, quinolinyl group, isoquinoline group, and the like. It is not limited to these.

Examples of halogen groups are fluorine, chlorine, bromine or iodine.

As used herein, the term "adjacent group" refers to a substituent immediately next to a corresponding substituent, and the next substituent includes a hydrogen atom not represented in the formula.

When a C ₂ to C ₄₀ alkenylene group is substituted, the substituent is substituted or unsubstituted C ₁ -C ₄₀ alkyl group, substituted or unsubstituted C ₂ -C ₄₀ alkenyl group, substituted or unsubstituted C ₂ -C ₄₀ At least _one selected from the group consisting of alkynyl groups, substituted or unsubstituted C ₁ -C ₄₀ alkoxy groups, substituted or unsubstituted C ₆ -C ₄₀ aryl groups, and substituted or unsubstituted C ₃ -C ₄₀ heteroaryl groups Qi.

Preferred specific examples of the compound of Formula 1 include the following compounds, but are not limited thereto.

Hereinafter, a method for preparing an anthracene derivative in which at least one triazole group of Formula 2 and Formula 3 is introduced into the compound of Formula 1 will be described.

The compound of Formula 1 may be prepared by introducing an aryl substituent to the anthracene derivative. Specifically, the compound of Formula 1 may be prepared by Suzuki bond reaction of 2-anthracene boronic acid or 2-anthracene boron ester derivative with an aryl halide derivative or heteroaryl halide derivative under a Pd catalyst.

Reactions other than the Suzuki binding reaction among the methods used when preparing the compound of Formula 1 may use a general method known in the art.

Specifically, the compound of Formula 1

1) preparing an anthraquinone derivative substituted with R4 by suzuki-coupling an anthraquinone derivative substituted with a halogen group and a boronic acid or boron ester compound having an R4 substituent under a Pd catalyst,

2) preparing a dialcohol derivative from the anthraquinone derivative prepared in step 1), and

3) by reducing the dialcohol derivative prepared in step 2) may be prepared by a method comprising the step of preparing an anthracene derivative. Such a manufacturing method may be represented by the following Scheme 1.

Scheme 1

In addition, the compound of Formula 1

1) preparing a dialcohol derivative from a halogen-substituted anthraquinone derivative,

2) preparing an anthracene derivative by reducing the dialcohol derivative prepared in step 1);

3) preparing the anthracene derivative prepared in step 2) as an anthracene boron ester derivative, and

4) Suzuki-coupling the anthracene boron ester derivative prepared in step 3) and the halide of R4 under a Pd catalyst to prepare a compound of Formula 1 wherein R4 is substituted. Such a manufacturing method may be represented by the following Scheme 2.

Scheme 2

Specifically, the substituent of Formula 2

1) reacting a L1 derivative substituted with a halogen group and methyl or ethyl ester with hydrazine monohydrate to form a L1 derivative substituted with a hydrazide group

2) introducing an R6 derivative having an acid chloride to the L1 derivative prepared in step 1), and

3) The material prepared in step 2) may be prepared by treating the R5 derivative having an NH ₂ group with POCl ₃ to prepare a triazole derivative substituted with L1, R5 and R6.

Such a manufacturing method may be represented by the following Scheme 3.

Scheme 3

Specifically, the substituent of Formula 3

1) a methyl or ethyl ester is substituted to react the R7 derivative with hydrazine monohydrate to form a R7 derivative substituted with a hydrazide group,

2) introducing an R8 derivative having an acid chloride into the R7 derivative prepared in step 1), and

3) treating the material prepared in step 2) with POCl ₃ together with the L 2 derivative having an NH ₂ group and a halogen group to prepare a triazole derivative substituted with L 2, R 7 and R 8; Can be.

Such a preparation method may be represented by the following Scheme 4.

Scheme 4

In addition, the present invention is an organic electronic device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, at least one of the organic material layer of Formula 1 It provides an organic electronic device comprising a compound.

The organic electronic device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electronic device, except that at least one organic material layer is formed using the anthracene derivative of the present invention described above.

Hereinafter, an organic light emitting device using the anthracene derivative of the present invention will be exemplified.

In one exemplary embodiment of the present invention, the organic light emitting diode may have a structure including a first electrode, a second electrode, and an organic material layer disposed therebetween. The organic material layer of the organic light emitting device of the present invention may be a single layer structure consisting of one layer, may be a multilayer structure of two or more layers including a light emitting layer. When the organic material layer of the organic light emitting device of the present invention has a multi-layer structure, for example, it may be a structure in which a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and the like are stacked. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers. For example, the organic light emitting device of the present invention may have a structure as shown in FIG. In Fig. 1, reference numeral 1 denotes a substrate, 2 an anode, 3 a hole injection layer, 4 a hole transport layer, 5 an organic light emitting layer, 6 an electron transport layer, and 7 a cathode. An organic light emitting device having a structure as shown in FIG. 1 is generally referred to as an organic light emitting device having a forward structure, but the present invention is not limited thereto and includes an organic light emitting device having a reverse structure. That is, the organic light emitting device of the present invention may have a structure in which a substrate, a cathode, an electron transport layer, an organic light emitting layer, a hole transport layer, a hole injection layer, and an anode are sequentially stacked.

When the organic light emitting device according to the present invention has an organic material layer of a multi-layer structure, the compound of Formula 1 is a light emitting layer, a hole transport layer, a layer for simultaneously transporting holes and light emission, a layer for simultaneously emitting light and electron transport, an electron transport layer, electron transport And / or injection layers and the like. In the present invention, the compound of Formula 1 is particularly preferably included in the electron injection and / or transport layer or light emitting layer.

The organic light emitting device according to the present invention may be manufactured using a conventional method and material for manufacturing an organic light emitting device, except that the anthracene derivative of Chemical Formula 1 is used in at least one layer of the organic material layer of the organic light emitting device. . For example, the organic light emitting device according to the present invention is a metal oxide or a metal oxide or alloy thereof having a conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, in order to fabricate an organic light emitting device having a reverse structure as described above, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic layer may be formed into a smaller number of layers by using a variety of polymer materials, but not by a deposition process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can manufacture.

As the cathode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the negative electrode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injecting materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer and transferring the holes to the light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.

The compound according to the present invention may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.

Hereinafter, preferred examples are provided to aid in understanding the present invention. However, the following examples are intended to illustrate the invention, whereby the scope of the invention is not limited.

<Manufacture example 1>

1-1. Compound Synthesis of Formulas 1-A, 1-B and 1-C

              [Formula 1-A] [Formula 1-B] [Formula 1-C]

6-bromo-2-naphthoic acid methyl ester compound (8.0 g, 30 mmol) and hydrazine monohydrate (6 mL, 120 mmol) were dissolved in 150 mL of methanol, stirred at room temperature for 2 hours, and then stirred at 80 ° C. Stir for 20 hours. After cooling to room temperature, the white solid formed was filtered and washed (methanol) and dried to prepare the compound of Formula 1-A (7.5 g, yield 94%). MS: [M + H] ⁺ = 265

After dissolving the compound of Formula 1-A (3.5 g, 13.2 mmol) and diisopropylethylamine (4.6 mL, 26.4 mmol) in 50 mL of xylene, benzoyl chloride (1.8 mL, 19.8 mmol) was added dropwise at 0 ° C. It was. After 20 minutes, the mixture was reacted at 140 ° C., and cooled to room temperature to form a white solid. The white solid formed was filtered, washed and dried to prepare the compound of Formula 1-B (3.5 g, yield 72%). MS: [M + H] ⁺ = 369

The compound of Formula 1-B (3.1 g, 8.5 mmol) and aniline (4.7 g, 51 mmol) were dispersed in 1,2-dichlorobenzene, and POCl ₃ (0.8 mL, 8.5 mmol) was slowly added dropwise. The reaction temperature was adjusted to 180 ° C., stirred for 4 hours, and cooled to room temperature again to form a white solid. After filtering this, the obtained solid was dispersed in 2M NaOH and stirred while heating to 70 ℃. The solid was filtered again, washed with plenty of water and dried to prepare the compound of Formula 1-C (2.6 g, 72% yield). MS: [M + H] ⁺ = 426

1-2. Synthesis of Compounds of Formulas 1-D and 1-E

                    [Formula 1-D] [Formula 1-E]

3-Bromobenzoic hydrazide (2.85 g, 13.2 mmol) and diisopropylethylamine (4.6 mL, 26.4 mmol) were dissolved in 50 mL of xylene, followed by benzoyl chloride (1.8 mL, 19.8). mmol) was added dropwise at 0 ° C. After 20 minutes, the mixture was reacted at 140 ° C., and cooled to room temperature to form a white solid. It was filtered and washed and dried to prepare the compound of Formula 1-D (3.0 g, 72% yield). MS: [M + H] ⁺ = 320

The compound of Formula 1-D (2.7 g, 8.5 mmol) and 1-aminonaphthalene (7.3 g, 51 mmol) were dispersed in 1,2-dichlorobenzene and POCl ₃ (0.8 mL, 8.5 mmol) was slowly added dropwise. . The reaction temperature was stirred at 180 ° C. for 6 hours, and then cooled to room temperature to form a white solid. The solid obtained after the filtration was dispersed in 2M NaOH and stirred while heating to 70 ℃. The solid was filtered again, washed with plenty of water and dried to prepare the compound of formula 1-E (2.07 g, yield 57%). MS: [M + H] ⁺ = 427

1-3. Synthesis of Compounds of Formulas 1-F and 1-G

                   [Formula 1-F] [Formula 1-G]

4-Bromobenzoic hydrazide (2-85 g, 13.2 mmol) and diisopropylethylamine (4.6 mL, 26.4 mmol) were dissolved in 50 mL of xylene, and then 4-tert-butyl benzoyl Chloride (3.9 g, 19.8 mmol) was added dropwise at 0 ° C. After 20 minutes, the mixture was reacted at 140 ° C., and cooled to room temperature to form a white solid. It was filtered and washed and dried to prepare the compound of Formula 1-F (3.5 g, yield 70%).

MS: [M + H] ⁺ = 376

The compound of Formula 1-F (3.2 g, 8.5 mmol) and aniline (4.7 g, 51 mmol) were dispersed in 1,2-dichlorobenzene and POCl ₃ (0.8 mL, 8.5 mmol) was slowly added dropwise. The reaction temperature was stirred at 180 ° C. for 4 hours, and then cooled to room temperature to form a white solid. The solid obtained after the filtration was dispersed in 2M NaOH and stirred while heating to 70 ℃. The solid was filtered again, washed with plenty of water and dried to prepare the compound of Formula 1-G (2.64 g, 72% yield). MS: [M + H] ⁺ = 433

1-4. Formulas 1-H and 1- Of I  Synthesis of Compound

                 Formula 1-H Formula 1-I

The compound of Chemical Formula 1-H was prepared by the same method as the preparation method of Chemical Formula 1-B, except that benzoic hydrazide was used instead of the 6-bromo-2-naphthoic acid methyl ester compound. MS: [M + H] ⁺ = 241

After dispersing the compound of Formula 1-H (3.2 g, 8.5 mmol) and 3-bromo-aniline (8.8 g, 51 mmol) in 1,2-dichlorobenzene, POCl ₃ (0.8 mL, 8.5 mmol) was slowly Added dropwise. The reaction temperature was 180 ° C., stirred for 4 hours, and cooled again to room temperature to obtain a white solid. The solid obtained after the filtration was dispersed in 2M NaOH and stirred while heating to 70 ℃. The solid was filtered again, washed with plenty of water and dried to prepare the compound of formula 1-I (2.1 g, yield 65%). MS: [M + H] ⁺ = 377

1-5. Synthesis of Compounds of Formulas 1-J and 1-K

                  [Formula 1-J] [Formula 1-K]

The compound of Chemical Formula 1-J was prepared by the same method as the preparation method of Chemical Formula 1-B, except that 4-bromo-benzoic hydrazide was used instead of the 6-bromo-2-naphthoic acid methyl ester compound. MS: [M + H] ⁺ = 320

The compound of Chemical Formula 1-K was obtained by the same method as the method of preparing Chemical Formula 1-C, except that Chemical Formula 1-J was used instead of Chemical Formula 1-B.

MS: [M + H] ⁺ = 377

1-6. Formulas 1-L and 1- M of  Synthesis of Compound

                 [Formula 1-L] [Formula 1-M]

The compound of Chemical Formula 1-L was prepared by the same method as the preparation method of Chemical Formula 1-H, except that 1-naphthoyl chloride was used instead of benzoyl chloride. MS: [M + H] ⁺ = 291

The compound of formula 1-L (2.4 g, 8.5 mmol) and 3-bromo-aniline (8.8 g, 51 mmol) were dispersed in 1,2-dichlorobenzene and POCl ₃ (0.8 mL, 8.5 mmol) was slowly Added dropwise. The reaction temperature was stirred at 180 ° C. for 4 hours, and then cooled to room temperature to give a white solid. The solid obtained after the filtration was dispersed in 2M NaOH and stirred while heating to 70 ℃. The solid was filtered again, washed with plenty of water and dried to prepare the compound of formula 1-M (2.35 g, yield 65%). MS: [M + H] ⁺ = 427

<Manufacture example 2>

2-1. Synthesis of Compound of Formula 2-A

[Formula 2-A]

2-bromo-9,10-dinaphthylanthracene (5.00 g, 9.82 mmol), bis (pinacolato) diboron (2.75 g, 10.9 mmol) and potassium acetate (2.89 g, 29.4 mmol) were added to dioxane ( 50 ml). Palladium (diphenylphosphinoferrocene) chloride (0.24 g, 3 mol%) was added to the suspension. The resulting mixture was stirred at 80 ° C. for about 6 hours and cooled to room temperature. The mixture was diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mL). The organic extract was dried over magnesium sulfate and concentrated in vacuo. The crude product was washed with ethanol and dried in vacuo to give the compound of formula 2-A (5.46 g, 92%) which was 9,10-dinaphthylanthracenyl-2-borate. MS: [M + H] ⁺ = 557

2-2. Synthesis of Compound of Formula 2-B

[Formula 2-B]

Carbazole (3.3 g, 20 mmol), 1-bromo-4-iodinebenzene (3.0 mL, 24 mmol), potassium carbonate (K ₂ CO ₃ , 5.6 g, 40 mmol), copper iodide (CuI, 1.9 g, 1.0 mmol) and 50 ml of xylene were refluxed under a nitrogen atmosphere. After cooling to room temperature, the product was extracted with ethyl acetate, water was removed with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. After passing through a silica gel column using a hexane solvent to obtain a compound, the solvent was removed under reduced pressure and dried under vacuum to prepare the compound of formula 2-B (1.6g, 25%) as a white solid. MS: [M + H] ⁺ = 322

2-3. Synthesis of Compound of Formula 2-C

[Formula 2-C]

The compound of formula 2-B (4.38 g, 13.2 mmol) was dissolved in dry tetrahydrofuran (80 mL) under nitrogen atmosphere. The solution was cooled to −78 ° C., and n-butyl lithium (6.6 mL, 2.5 M hexane solution) was slowly added to the cooled solution over 10 minutes and then stirred at −78 ° C. for about 40 minutes. 2-Bromoanthraquinone compound (3.59 g, 5.5 mmol) was added to the reaction mixture and further stirred at −78 ° C. for about 3 hours. The mixture was stirred at rt for about 1 h. To the mixture was added aqueous ammonium chloride solution (50 mL). The organic layer was separated and the aqueous layer was extracted with diethyl ether (60 mL). The extracted organic solution layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained solid was suspended with diethyl ether, stirred for 1 hour and then filtered. After drying, the compound of formula 2-C (3.32 g, 73%) was prepared as a dialcohol compound.

MS [M + H] ⁺ = 773

2-4. Synthesis of Compound of Formula 2-D

[Formula 2-D]

The compound of formula 2-C (2.82 g, 3.65 mmol) was added to a dispersion of acetic acid (60 mL), potassium iodide (3.32 g, 20 mmol) and sodium hypophosphite hydrate (3.52 g, 40 mmol). The mixture was refluxed for about 3 hours with continued stirring and then cooled to room temperature. The mixture was filtered, washed with water and dried in vacuo to give the compound of formula 2-D (2.87 g, 90%). MS: [M + H] ⁺ = 739

2-5 Synthesis of Compound of Formula 2-E

[Formula 2-E]

Except for using the compound of formula 2-D instead of 2-bromo-9,10-dinaphthylanthracene and bis (pinacolato) diboron in the method for preparing a compound of formula 2-A of Preparation Example 2 Was prepared in the same manner as the method for preparing the compound of formula 2-A. MS [M + H] ⁺ = 787

2-6. Synthesis of Compound of Formula 2-F

[Formula 2-F]

Dissolve 1-bromonaphthalene (34.8 g, 168.2 mmol) in tetrahydrofuran (170 mL), lower the temperature to -78 ° C and slowly add n-butyllithium (67.3 mL, 168,2 mmol) for 1 hour. Was stirred. 2-bromoanthraquinone (21 g, 73.1 mmol) was added and the temperature was raised to room temperature and stirred for 3 hours. Aqueous solution of saturated ammonium chloride was added thereto, the water layer was removed, dried over anhydrous magnesium sulfate, filtered and dried under reduced pressure. Recrystallization with ethyl ether and petroleum ether to prepare the compound of formula 2-F (32.3 g, 82%). MS: [M + H] ⁺ = 544

2-7. Synthesis of Compound of Formula 2-G

[Formula 2-G]

The compound of Chemical Formula 2-F (32.3 g, 59.5 mmol), potassium iodide (29.6 g, 178.4 mmol) and sodium hypophosphite (38 g, 256.8 mmol) were added to acetic acid (40 mL), and the mixture was heated and stirred for 3 hours at room temperature. After lowering the temperature, the precipitate was filtered and then recrystallized with ethanol to prepare the compound of Chemical Formula 2-G (25.5 g, 84%). MS: [M + H] ⁺ = 509

2-8. Synthesis of Compound of Formula 2-H

[Formula 2-H]

Method of synthesizing the compound of Formula 2-A, except that Formula 2-G was used instead of 2-bromo-9,10-dinaphthylanthracene in the synthesis of Compound 2-A of Preparation Example 2 Synthesis was carried out in the same manner as to prepare a compound of Formula 2-H. MS: [M + H] ⁺ = 557

2-9. Synthesis of Compound of Formula 2-I

[Formula 2-I]

Except that 1-bromo-4- (2-naphthyl) benzene was used instead of 1-bromonaphthalene in the synthesis of the compound of Formula 2-F of Preparation Example 2, the compound of Formula 2-F was synthesized The compound of Formula 2-I was prepared in the same manner as one method.

MS: [M + H] ⁺ = 696

2-10. Synthesis of Compound of Formula 2-J

[Formula 2-J]

Except for using the compound of formula 2-I instead of the compound of formula 2-F in the synthesis of the compound of formula 2-G of Preparation Example 2 in the same manner as the method of synthesizing the compound of formula 2-G The compound of Formula 2-J was prepared.

MS: [M + H] ⁺ = 661

2-11. Synthesis of Compound of Formula 2-K

[Formula 2-K]

Except for using the compound of formula 2-J instead of 2-bromo-9,10- dinaphthylanthracene in the synthesis of the compound of formula 2-A of Preparation Example 2 to synthesize the compound of formula 2-A The compound of Chemical Formula 2-K was prepared in the same manner as one method. MS: [M + H] ⁺ = 709

Preparation Example 3 Synthesis of Compound of Formula 1-1

3-1. Synthesis of Compounds of Formulas 3-A, 3-B, 3-C and Formula 1-1

                         [Formula 3-A] [Formula 3-B]

                 [Formula 3-C] [Formula 1-1]

2-anthraquinonecarboxyl chloride (10.0 g, 37 mmol) and benzoic hydrazide (7.0 g, 51 mmol) were dissolved in 250 ml of xylene and stirred at room temperature for 1 hour. Then, refluxed for 3 hours. The white solid formed after cooling to room temperature was filtered, washed (benzene) and dried to prepare the compound of Chemical Formula 3-A (12.9 g, yield 94%). MS: [M + H] ⁺ = 371

Formula 3-A (3.0 g, 8 mmol) and phosphorus pentachloride (PCl ₅ , 8 g, 38 mmol) are mixed and left to melt at 145 ° C. for 30 minutes. After cooling, benzene was poured to precipitate a yellow solid, which was then filtered and washed (benzene) and dried. The yellow solid (1.8 g, 4.4 mol) was mixed with 10 ml of dimethylarylene and 0.44 ml of aniline and maintained at 180 ° C, followed by stirring for 1 hour. After lowering to room temperature, 1N HCl was poured to precipitate a solid, which was filtered. The resulting solid was recrystallized with acetic acid, filtered and dried to prepare the above Chemical Formula 3-B (0.66 g, 20% yield). MS: [M + H] ⁺ = 427

2-bromo naphthalene (1.3 g, 6.1 mmol) was dissolved in dry tetrahydrofuran (30 mL) under nitrogen atmosphere. The solution was cooled to −78 ° C. and n-butyl lithium (2.2 mL, 2.5 M hexane solution) was slowly added to the cooled solution over 10 minutes and then stirred at −78 ° C. for about 40 minutes. Formula 3-B (0.66 g, 1.54 mmol) was added to the reaction mixture and further stirred at −78 ° C. for about 3 hours. The mixture was stirred at rt for about 1 h. To the mixture was added aqueous ammonium chloride solution (5 mL). The organic layer was separated and the aqueous layer was extracted with diethyl ether (20 mL). The extracted organic solution layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained solid was suspended with diethyl ether, stirred for 1 hour and then filtered. After drying, a compound of formula 3-C (0.42 g, 40%) was prepared as a dialcohol compound. MS [M + H] ⁺ = 684

The compound of formula 3-C (0.4 g, 0.6 mmol) was added to a dispersion of acetic acid (10 mL), potassium iodide (1.0 g, 6 mmol) and sodium hypophosphite hydrate (1.3 g, 14 mmol). The mixture was refluxed for about 3 hours with continued stirring and then cooled to room temperature. The mixture was filtered, washed with water and dried in vacuo to give the compound of formula 1-1 (0.3 g, 77%). 2 shows the MS value of the compound of Formula 1-1 in a graph. MS: [M + H] ⁺ = 650

<Manufacture example 4>

4-1. Synthesis of Compound of Formula 1-51

[Formula 1-51]

After dissolving the compound of Formula 2-A (3.5 g, 6.3 mmol) and the compound of Formula 1-K (2.6 g, 6.9 mmol) in tetrahydrofuran (100 mL), 2 M aqueous potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and tetrahydrofuran: hexane = 1: 6 to prepare a compound of Chemical Formula 1-51 (3.0 g, 66%). 3 shows the MS value of the compound of Formula 1-51 in a graph. MS: [M + H] ⁺ = 726

4-2. Synthesis of Compound of Formula 1-91

[Formula 1-91]

After dissolving the compound of Formula 2-A (3.5 g, 6.3 mmol) and the compound of Formula 1-G (2.98 g, 6.9 mmol) in tetrahydrofuran (100 mL), 2 M potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and tetrahydrofuran: hexane = 1: 6 to prepare a compound of Chemical Formula 1-91 (2.95 g, 60%).

MS: [M + H] ⁺ = 783

4-3. Synthesis of Compound of Formula 1-111

[Formula 1-111]

After dissolving the compound of Formula 2-A (3.5 g, 6.3 mmol) and the compound of Formula 1-E (2.94 g, 6.9 mmol) in tetrahydrofuran (100 mL), 2 M potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and tetrahydrofuran: hexane = 1: 6 to prepare a compound of Chemical Formula 1-111 (3.4 g, 70%).

MS: [M + H] ⁺ = 776

4-4. Synthesis of Compound of Formula 1-113

[Formula 1-113]

The compound of formula 2-G (3.5 g, 6.3 mmol) and the compound of formula 1-E (2.94 g, 6.9 mmol) were completely dissolved in tetrahydrofuran (100 mL), followed by adding 2 M aqueous potassium carbonate solution. Keystriphenylphosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and tetrahydrofuran: hexane = 1: 6 to prepare a compound of Chemical Formula 1-113 (3.4 g, 70%).

MS: [M + H] ⁺ = 776

4-5. Synthesis of Compound of Formula 1-151

[Formula 1-151]

After dissolving the compound of Formula 2-A (3.5 g, 6.3 mmol) and the compound of Formula 1-C (2.94 g, 6.9 mmol) in tetrahydrofuran (100 mL), 2 M potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and tetrahydrofuran: hexane = 1: 6 to prepare a compound of Chemical Formula 1-151 (3.4 g, 70%). 4 shows the MS value of the compound of Formula 1-151 as a graph. MS: [M + H] ⁺ = 776

4-6. Synthesis of Compound of Formula 2-101

[Formula 2-101]

After dissolving the compound of Formula 2-A (3.5 g, 6.3 mmol) and the compound of Formula 1-I (2.6 g, 6.9 mmol) in tetrahydrofuran (100 mL), 2 M aqueous potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and tetrahydrofuran: hexane = 1: 6 to prepare the compound of Chemical Formula 2-101 (3.4 g, 75%). 5 is a graph showing the MS value of the compound of formula 2-101. MS: [M + H] ⁺ = 726

4-7. Synthesis of Compound of Formula 2-105

[Formula 2-105]

After completely dissolving the compound of Formula 2-E (4.95 g, 6.3 mmol) and the compound of Formula 1-I (2.6 g, 6.9 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and tetrahydrofuran: hexane = 1: 6 to prepare a compound of Chemical Formula 2-105 (4.2 g, 70%).

MS: [M + H] ⁺ = 957

4-8. Synthesis of Compound of Formula 2-116

[Formula 2-116]

After completely dissolving the compound of Formula 2-K (4.47 g, 6.3 mmol) and the compound of Formula 1-M (2.94 g, 6.9 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and tetrahydrofuran: hexane = 1: 6 to prepare a compound of Chemical Formula 2-116 (3.74 g, 64%).

MS: [M + H] ⁺ = 929

< Experimental Example  1>

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1500 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.

[HAT]

4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400 kPa) of the following formula, which is a material for transporting holes on the hole injection layer, is vacuum deposited to form a hole transport layer Formed.

[NPB]

Subsequently, Alq ₃ (aluminum tris (8-hydroxyquinoline)) of the following formula was vacuum deposited on the hole transport layer to a thickness of 300 Pa to form a light emitting layer.

[Alq ₃ ]

The compound of Formula 1-1 prepared in Preparation Example 1 was vacuum deposited to a thickness of 200 kPa on the light emitting layer to form an electron injection and transport layer.

On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to have a thickness of 12 kW in order to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å / sec, aluminum is 2 Å / sec, the vacuum degree during deposition is 2 × 10 ⁻⁷ to 5 × 10 ⁻⁸ torr was maintained.

When a forward electric field of 5.6 V was applied to the organic light emitting device, green light corresponding to x = 0.32 and y = 0.55 was observed based on the 1931 CIE color coordinate at a current density of 50 mA / cm 2. , A green light of 2.6 cd / A was observed at a current density of 100 mA / cm 2 with a forward electric field of 6.4 V.

< Experimental Example  2>

Hexanitrile hexaazatriphenylene (500 Hz), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) on an ITO electrode prepared in the same manner as in Experimental Example 1 (400 kPa), Alq ₃ (300 kPa), and the compounds of Formulas 1-51 (200 kPa) were sequentially thermally vacuum deposited to form a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer in that order.

An organic light emitting device was manufactured by sequentially depositing aluminum having a thickness of 12 Å and lithium fluoride (LiF) DHK 2000 Å on the electron transport layer to form a cathode.

The deposition rate of the organic material in the above process was maintained at 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was 0.3 Å / sec, the aluminum was deposited at a rate of 2 Å / sec, the deposition upon the degree of vacuum 2 × 10 ^{- 7} to 5 x 10 ^-8 torr was maintained.

As a result of applying a forward electric field of 5.7 V to the organic light emitting device, green light corresponding to x = 0.33 and y = 0.56 was observed based on the 1931 CIE color coordinate at a current density of 50 mA / cm 2, and the 6.8 V When the forward electric field was applied, green light of 2.49 cd / A was observed at a current density of 100 mA / cm 2.

< Experimental Example  3>

Hexanitrile hexaazatriphenylene (500 Hz), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) on an ITO electrode prepared in the same manner as in Experimental Example 1 (400 kPa) and the compound of Chemical Formula 1-151 (400 kPa) were sequentially thermally vacuum deposited to form a hole injection layer, a hole transport layer, and a layer for simultaneously emitting and electron transport.

An organic light emitting device was manufactured by depositing lithium fluoride (LiF) having a thickness of 12 kW and aluminum having a thickness of 2000 kW sequentially on the layer simultaneously emitting light and transporting electrons.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å / sec, aluminum is 2 Å / sec, the vacuum degree during deposition is 2 × 10 ⁻⁷ to 5 × 10 ⁻⁸ torr was maintained.

As a result of applying a forward electric field of 5.8 V to the organic light emitting device manufactured above, green light corresponding to x = 0.33 and y = 0.58 was observed based on the 1931 CIE color coordinate at a current density of 50 mA / cm 2, and a value of 6.9 V As a result of applying the forward electric field, 2.6 cd / A of green light was observed at a current density of 100 mA / cm 2.

< Experimental Example  4>

Hexanitrile hexaazatriphenylene (500 Hz), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) on an ITO electrode prepared in the same manner as in Experimental Example 1 (400 Å), Alq ₃ (300 Å), the compound of formula 2-101 (200 Å), and lithium fluoride (LiF) 12 순차적 in order to thermally vacuum deposit a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer And the electron injection layer were formed in order. 2000 nm thick aluminum was deposited thereon to form a cathode to manufacture an organic light emitting device.

As a result of applying a forward electric field of 4.8 V to the organic light emitting device, green light corresponding to x = 0.32 and y = 0.56 was observed based on a 1931 CIE color coordinate at a current density of 50 mA / cm 2. In addition, when a forward electric field of 5.7 V was applied, green light of 2.8 cd / A was observed at a current density of 100 mA / cm 2.

< Experimental Example  5>

Hexanitrile hexaazatriphenylene (500 Hz), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) on an ITO electrode prepared in the same manner as in Experimental Example 1 (400 Å), Alq ₃ (300 Å), the compound of formula 2-116 (200 Å), and lithium fluoride (LiF) 12 순차적 in succession by thermal vacuum deposition to form a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer And an electron injection layer were formed in turn. 2000 nm thick aluminum was deposited thereon to form a cathode to manufacture an organic light emitting device.

As a result of applying a forward electric field of 4.9 V to the organic light emitting device, green light corresponding to x = 0.33 and y = 0.58 was observed based on a 1931 CIE color coordinate at a current density of 50 mA / cm 2. In addition, when a forward electric field of 5.8 V was applied, green light of 2.7 cd / A was observed at a current density of 100 mA / cm 2.

The novel anthracene compound according to the present invention may be used as an organic material layer material of an organic electronic device including an organic light emitting device by introducing a triazole derivative into the anthracene compound. The organic electronic device including the organic light emitting device using the anthracene compound according to the present invention as a material of the organic material layer has excellent characteristics in efficiency, driving voltage, lifespan, and the like.

Claims (18)

Anthracene derivative represented by the following formula (1): <Formula 1>

In Chemical Formula 1, R1 and R2 are the same as or different from each other, independently halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ alkoxy group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ of, C ₃ Unsubstituted or substituted with one or more groups selected from the group consisting of -C ₄₀ cycloalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, C ₆ -C ₄₀ aryl group, C ₃ -C ₄₀ heteroaryl group, and arylamine group An aryl group of C ₆ to C ₄₀ ; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C _It is selected from the group consisting of C ₆ ~ C ₄₀ amine group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group, At least one of R3 and R4 is a group of formula (2) or a group of formula (3), <Formula 2>

In Chemical Formula 2, L 1 is a direct bond; A C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, a C ₂ -C ₄₀ alkynyl group of, C ₁ -C ₄₀ alkoxy group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ C ₂ -C ₄₀ alkenylene group unsubstituted or substituted with one or more groups selected from the group consisting of a heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C _It is selected from the group consisting of C ₆ ~ C ₄₀ arylamine group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group, R5 and R6 are the same as or different from each other, and hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted cycloalkyl group of C ₃ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an alkoxy group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or selected from the group consisting of a heteroaryl unsubstituted C ₃ ~ C ₄₀ of , <Formula 3>

In Chemical Formula 3, L 2 is a direct bond; A C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, a C ₂ -C ₄₀ alkynyl group of, C ₁ -C ₄₀ alkoxy group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ C ₂ -C ₄₀ alkenylene group unsubstituted or substituted with one or more groups selected from the group consisting of a heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C _It is selected from the group consisting of C ₆ ~ C ₄₀ arylamino group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group, R7 and R8 are the same as or different from each other, hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted cycloalkyl group of C ₃ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an alkoxy group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or is selected from the group consisting of a heteroaryl unsubstituted C ₃ ~ C ₄₀ , When one of R4 of R3 is a group of formula (2) or a group of formula (3), the other is halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ From a group consisting of a C ₄₀ alkoxy group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, a C ₃ to C ₄₀ heteroaryl group and an arylamine group A C ₆ -C ₄₀ aryl group unsubstituted or substituted with one or more selected groups; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C _It is selected from the group consisting of C ₆ ~ C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group. The anthracene derivative according to claim 1, wherein R 1 and R 2 in Formula 1 are the same aryl group. The anthracene derivative according to claim 1, wherein R 1 and R 2 in Formula 1 are the same heteroaryl group. The anthracene derivative according to claim 1, wherein R1 and R2 of Formula 1 are amino groups substituted with the same C ₆ -C ₄₀ aryl group or C ₃ -C ₄₀ heteroaryl group. The anthracene derivative according to claim 1, wherein R 1 and R 2 of Formula 1 are independently selected from the group consisting of the following structural formulas:

In the above structural formula, Z1 to Z3 are the same as or different from each other, and independently halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group Unsubstituted or substituted with one or more groups selected from the group consisting of C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₃ to C ₄₀ heteroaryl group C ₆ -C ₄₀ aryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group substituted with one or more selected from the group consisting of unsubstituted C ₃ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C _It is selected from the group consisting of C ₆ ~ C ₄₀ amine group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₃ ~ C ₄₀ heteroaryl group. The anthracene derivative according to claim 1, wherein L 1 in Formula 2 is any one selected from a direct bond, an unsubstituted C ₆ -C ₄₀ arylene group, and an unsubstituted C ₅ -C ₄₀ heteroarylene group. The anthracene derivative according to claim 1, wherein at least one of R5 and R6 of Formula 2 is a C ₆ to C ₄₀ aryl group unsubstituted or substituted with an alkyl group of C ₁ to C ₄₀ or an aryl group of C ₆ to C ₄₀ . The anthracene derivative according to claim 1, wherein L 2 of Formula 3 is any one selected from a direct bond, an unsubstituted C ₆ -C ₄₀ arylene group, and an unsubstituted C ₅ -C ₄₀ heteroarylene group. The anthracene derivative according to claim 1, wherein at least one of R7 and R8 of Formula 3 is a C ₆ -C ₄₀ aryl group unsubstituted or substituted with an alkyl group of C ₁ -C ₄₀ or an aryl group of C ₆ -C ₄₀ . The method of claim 1, wherein the alkyl group is selected from methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, hexyl group and heptyl group, the cycloalkyl group is cyclopentyl group and cyclohexyl group The alkenyl group is an alkenyl group substituted with an aryl group of a stylbenyl group or a styrenyl group, the alkoxy group is an alkoxy group having 1 to 40 carbon atoms, and the aryl group is a phenyl group, a naphthyl group, and an anthra group. A phenyl amine, a naphthylamine, a biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl, and a aryl amine group. -Naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group Is chosen and said The logoeri group is selected from pyridyl group, bipyridyl group, triazine group, acridil group, thiophene group, furan group, imidazole group, oxazole group, thiazole group, triazole group, quinolinyl group and isoquinoline group, and the halogen The group is an anthracene derivative selected from fluorine, chlorine, bromine and iodine. An organic electronic device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is an anthracene derivative according to any one of claims 1 to 10. Organic electronic device comprising a. The organic electronic device of claim 11, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor. The organic electronic device of claim 11, wherein the organic electronic device is an organic light emitting device. The organic electronic device of claim 13, wherein the organic light emitting device is an organic light emitting device having a forward structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. The organic electronic device of claim 13, wherein the organic light emitting device is an organic light emitting device having a reverse structure in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. The organic light emitting device of claim 13, wherein the organic light emitting device includes an anthracene derivative according to any one of claims 1 to 10, wherein the organic material layer including any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and a transport layer comprises an anthracene derivative according to any one of claims 1 to 10. device. The organic electronic device of claim 13, wherein the organic material layer comprises a light emitting layer, and the light emitting layer is formed of the anthracene derivative of claim 1. The organic electronic device of claim 13, wherein the organic material layer includes an electron transporting layer or an injection layer, and the layer includes the anthracene derivative of claim 1.

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