KR20100007143A - New anthracene derivatives and organic electronic device using the same - Google Patents

Abstract

PURPOSE: An anthracene derivative is provided to be used as an organic layer material of an organic electronic device including an organic light-emitting device, to improve efficiency, lifetime, and stability and to lower driving voltage. CONSTITUTION: An anthracene derivative has a structure represented by chemical formula 1. An organic electronic device comprises a first electrode, a second electrode, and at least one organic material layer arranged between the first and second electrodes. The organic material layer comprises the anthracene derivative. The organic material device is selected from the group consisting of an organic light-emitting device, an organic solar cell, a organic photoconducting drum and an organic transistor.

Description

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

The present invention relates to a novel anthracene derivative 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 the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor, all of which are electron / hole injection materials, electron / hole extraction materials, electron / holes for driving the device. Requires a transport material or a luminescent material. 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. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. 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 may be classified into blue, green, and red luminescent materials and yellow and orange luminescent materials required to achieve better natural colors according to 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 a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than a host mainly constituting the light emitting layer is mixed in the light emitting layer, and 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. Must be preceded.

Among them, as the electron transporting material, organometallic complexes having excellent stability to electrons and an electron moving speed as organic monomolecular materials are preferable. Among them, Alq ₃ having excellent stability and high electron affinity has been reported to be the most excellent, but when used in a blue light emitting device, there is a problem in that color purity is poor due to light emission due to exciton diffusion. In addition, Sanyo's flavone derivatives or Chiso's germanium and silicon chloropetadiene derivatives are known (Japanese Laid-Open Patent Publication No. 1998-017860, Japanese Laid-Open Patent Publication No. 1999-087067). .

In addition, as the organic monomolecular substance, PBD (2-biphenyl-4-yl-5- (4-t-butylphenyl) -1,3,4-oxadiazole) derivative bonded to a spiro compound and hole blocking ability And TPBI (2,2 ', 2 "-(benzene-1,3,5-triyl) -tris (1-phenyl-1H-benzimidazole), which has good electron transport ability (Adv. Mater. 10). , 1998, 1136 & Tao et al, Appl. Phys. Lett. 77, 2000, 1575. In particular, benzo imidazole derivatives published by LG Chem are widely known for their excellent durability.

The organic light emitting device using the organic monomolecular material as an electron transporting layer has short light emission lifetime, low durability, and low reliability. These problems are due to the lack of physical or chemical changes of organic materials, photochemical or electrochemical changes of organic materials, oxidation of the cathode, peeling and durability.

Therefore, organic light emitting devices using a method of obtaining an arbitrary emission color by changing the structure of the organic monomolecular material used in the organic light emitting device or obtaining various high efficiency by the host dopant system have been proposed. It lacks properties, life and durability.

As a solution to the above problems, for example, Korean Patent Laid-Open Publication No. 2003-0067773 discloses a compound having a benzo imidazole wheel and anthracene skeleton.

However, there is a continuous demand for the development of new materials having improved light emission luminance, light emission efficiency, lifespan, and the like than organic EL devices using such compounds.

In order to solve the above problems of the prior art, the inventors have discovered a novel anthracene derivative. In addition, it has been found that when the organic layer of the organic electronic device is formed using the novel anthracene derivative, effects such as efficiency increase, driving voltage drop, life extension, and stability increase of the device may be exhibited.

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

One aspect of the present invention for achieving the above object provides a novel anthracene derivative.

A second aspect of the present invention for achieving the above object, 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 layer of the organic material layer provides an organic electronic device comprising the novel anthracene derivative.

The novel anthracene derivative according to the present invention can be used as an organic material layer of organic electronic devices including organic light emitting devices, and organic electronic devices including organic light emitting devices using the same have excellent efficiency in increasing efficiency, lowering driving voltage, extending life, and increasing stability. Characteristics.

Hereinafter, the present invention will be described in more detail.

One aspect of the present invention relates to a novel anthracene derivative represented by the 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 ~ C ₄₀ cycloalkyl group, C ₂ ~ C ₄₀ of the heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted carbazolyl group, and a C ₅ ~ least one selected from the heteroaryl group consisting of C ₄₀ of C ₆ ~ C ₄₀ aryl group unsubstituted or substituted with a 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 ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ 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 ₂ ~ C ₄₀ A fluorenyl 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 ₅ -C ₄₀ heteroaryl group; 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 ₂ ~ C _Is selected from the group consisting of an amino group unsubstituted or substituted with at least one group selected from the group consisting of ₄₀ heterocycloalkyl groups, C ₆ -C ₄₀ aryl groups and C ₅ -C ₄₀ heteroaryl groups,

R3 is a group represented by any one of the following Formulas 2 to 9,

 [Formula 2] [Formula 3] [Formula 4]

 [Formula 5] [Formula 6] [Formula 7]

 [Formula 8] [Formula 9]

In Chemical Formulas 2 to 9,

X and Y are each CH or N,

R11 to R24 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 ₂ ~ 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 ₅ -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 ₂ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl 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 ₅ -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 ₂ ~ C ₄₀ A C ₂ -C ₄₀ alkenyl group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -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 ₂ ~ C ₄₀ A C ₁ to C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to 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 ₂ ~ C An amino group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl groups, C ₆ -C ₄₀ aryl groups, and C ₅ -C ₄₀ heteroaryl 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 ₂ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or 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 ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of a group is selected from the group consisting of a heteroaryl unsubstituted C ₅ ~ C ₄₀ of Can and

R11 and R12, and R14 and R15 may be connected to each other to form a condensed ring,

In Formula 9, when Y is CH, it may be connected to R23 or R24 group to form a condensed ring.

L ₁ to L ₈ are direct bonds; 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 a C ₅ ~ 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 ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted aryl group of C ₆ ~ C ₄₀ 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 ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; 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 ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ the aryl group and the C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C ₄₀ arylamine 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 ₂ ~ C ₄₀ A C ₂₅ -C ₄₀ spiro 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 ₅ -C ₄₀ heteroaryl group; 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 ₂ ~ C Selected from the group consisting of C ₂₅ -C ₄₀ open spiro groups unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl groups, C ₆ -C ₄₀ aryl groups and C ₅ -C ₄₀ heteroaryl groups Become,

R4 to R10 are each independently 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 ₂ ~ 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 ₅ -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 ₂ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl 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 ₅ -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 ₂ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or 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 ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or 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 ₂ 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 ₅ ~ C ₄₀ heteroaryl group.

In the anthracene derivative represented by Formula 1, R1 and R2 are preferably the same aryl group, and more preferably substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, and the like.

In addition, in the anthracene derivative represented by Formula 1, R1 and R2 are preferably the same heteroaryl group, more preferably a substituted or unsubstituted pyridyl group, bipyridyl group, quinoline group, isoquinoline group and the like.

In addition, in the anthracene derivative represented by Formula 1, R1 and R2 is preferably an amino group substituted with the same C ₆ ~ C ₄₀ aryl group or C ₅ ~ C ₄₀ heteroaryl group.

In addition, in the anthracene derivative represented by Formula 1, R1 and R2 are preferably selected from the group consisting of:

Z 1 to Z 3 in the formula 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 ₂ ~ 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 ₅ -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 ₂ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -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 ₂ ~ C ₄₀ A C ₂ -C ₄₀ alkenyl group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -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 ₂ ~ C ₄₀ A C ₁ to C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to 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 ₂ ~ C ₄₀ An 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 ₅ -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 ₂ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or 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 ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ 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 ₅ ~ C ₄₀ Can be.

L ₁ to L ₈ are each independently a direct bond or preferably selected from the group consisting of:

Substituents used in the present invention can be defined as follows.

It is preferable that an alkyl group is C1-C40, and does not give a steric hindrance. Specific examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, hexyl group and heptyl group, but are not limited thereto.

It is preferable that a cycloalkyl group is C3-C40 and does not give a steric hindrance. Specifically, there are cyclopentyl group, cyclohexyl group, and the like, but is not limited thereto.

As the alkenyl group having 2 to 40 carbon atoms, an alkenyl group in which an aryl group such as a stilbenyl group or a styrenyl group is substituted is preferable, but is not limited thereto.

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

As an aryl group, it is preferable that it is C6-C40. Specifically, phenyl group, naphthyl group, anthracenyl group, biphenyl group, pyrenyl group, perylene group and derivatives thereof, and the like, but are not limited thereto.

Examples of the aryl amine group include a phenylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, and 2-methyl-biphenylamine group. , 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole, triphenyl amine group and the like, but are not limited thereto.

Examples of the heterocyclic group include 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. It is not limited only to these.

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

Spiro is a structure in which two ring organic compounds are connected to one atom,

Etc., but is not limited thereto.

An open spiro is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected to one atom.

Etc., but is not limited thereto.

The substituted C ₂ -C ₄₀ alkenylene group is C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₁ -C ₄₀ alkoxy group, C _6- It is preferably substituted with one or more groups selected from the group consisting of C ₄₀ aryl groups and C ₃ -C ₄₀ heteroaryl groups.

In addition, it is preferred that R3 of formula (I) is represented by the general formula (2), when the R4 to R10 is a hydrogen, R1, R2, L _1, and R11 to R13 is represented by the following formula.

In particular, when R3 of Formula 1 is represented by Formula 2, and R11 and R12 are connected to each other to form a condensed ring, the anthracene derivative represented by Formula 1 preferably includes a compound represented by the following formula Do.

In addition, when R3 of Formula 1 is represented by Formula 3, and R4 to R10 is hydrogen, R1, R2, L ₂ and R14 to R16 are preferably represented by the following formula.

In particular, when R3 of Formula 1 is represented by Formula 3, and R14 and R15 are connected to each other to form a condensed ring, the anthracene derivative represented by Formula 1 preferably includes a compound represented by the following formula Do.

In addition, it is preferred that R3 of formula (I) is represented by the general formula (4), when the R4 to R10 is a hydrogen, R1, R2, L _3, R17 and R18 is represented by the following formula.

In addition, it is preferred that R3 of formula (I) is represented by the general formula (5), when the R4 to R10 is a hydrogen, R1, R2, L _4, R19 and R20 is represented by the following formula.

In addition, when R3 of Formula 1 is represented by Formula 6, and R4 to R10 is hydrogen, R1, R2, L ₅ , R21 and R22 is preferably represented by the following formula.

In addition, when R3 of Formula 1 is represented by Formula 7 and R4 to R10 is hydrogen, the compound represented by Formula 1 preferably includes a compound represented by the following formula.

In addition, when R 3 of Formula 1 is represented by Formula 8, and R4 to R10 is hydrogen, the compound represented by Formula 1 preferably includes a compound represented by the following formula.

In addition, when R 3 of Formula 1 is represented by Formula 9, and R4 to R10 is hydrogen, the compound represented by Formula 1 preferably includes a compound represented by the following formula.

The anthracene derivative represented by Formula 1 according to the present invention can be synthesized using a known synthesis method such as Suzuki coupling reaction.

A second aspect of the present invention is an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers is claim 1 to 16 It relates to an organic electronic device comprising any one of the anthracene derivatives.

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 above-described compounds.

Hereinafter, an organic light emitting diode 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 organic light emitting devices 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 anthracene derivative represented by the 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 And electron transport and / or injection layers. 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 is an anthracene derivative represented by the above formula (1) except that it is used in at least one layer of the organic material layer of the organic light emitting device, can be prepared using a conventional method and material for manufacturing an organic light emitting device Can be. 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 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, an 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 positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection 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 transport material, a material capable of transporting holes from the anode or the hole injection layer to be transferred 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; Bis-methyl-8-hydroxyquinoline paraphenylphenol aluminum complex (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 transport 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 novel anthracene derivatives 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 photoconductor (OPC) drums, organic transistors, and the like.

That is, the organic electronic device is preferably 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 material layer of the organic light emitting device includes an electron transport and / or injection layer, it is preferable that the layer includes the anthracene derivative.

In addition, the organic material layer of the organic light emitting device may include a layer for simultaneously transporting holes and emitting light, or may include a layer for simultaneously emitting light and transport electrons.

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.

< Production Example  1> Synthesis of Compound of Formula 1-A

[Formula 1-A]

Under nitrogen atmosphere, 1,8-dichloroanthraquinone (50 g, 0.18 mol), phenylboronic acid (48 g, 0.4 mol), Pd (PPh ₃ ) ₄ (6.3 g, 2.17 mmol) were added to a 2M K ₂ CO ₃ aqueous solution. (200 mL) and THF (400 mL) were stirred at reflux for about 12 hours. After the reaction, the mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with THF / EtOH to obtain Compound 1-A (47 g, 72%). MS [M] = 360

< Production Example  2> Synthesis of Compound of Formula 1-B

[Formula 1-B]

Under nitrogen atmosphere, 1,8-dichloroanthraquinone (20 g, 72.2 mmol), 2-naphthalene boronic acid (27.3 g, 158 mmol), Pd (PPh ₃ ) ₄ (2.5 g, 2.17 mmol) was added to 2M K ₂ CO ₃ The solution was added to an aqueous solution (100 mL) and THF (500 mL) and stirred at reflux for about 12 hours. After the reaction, the mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with THF / EtOH to obtain Compound 1-B (17 g, 52%). MS [M] = 460

< Production Example  3> Synthesis of Compound of Formula 1-C

[Formula 1-C]

Compound 1-A (11.2 g, 20.5 mmol) prepared in Preparation Example 1 was dispersed in acetic acid (200 mL) under a nitrogen atmosphere, followed by 57% HI (500 mL) and 50% H ₃ PO ₂ (250 mL). After the addition, the mixture was stirred while boiling for 4 days. After cooling to room temperature, the mixture was separated with chloroform, and the organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with EtOH to obtain Compound 1-C (58 g, 65%). MS [M] = 330

< Production Example  4> Synthesis of Compound of Formula 1-D

[Formula 1-D]

Compound 1-B (16 g, 34.7 mmol) prepared in Preparation Example 2 was dispersed in acetic acid (750 mL) under a nitrogen atmosphere, followed by 57% HI (100 mL) and 50% H ₃ PO ₂ (50 mL). After addition, the mixture was stirred at reflux for 3 days. After the reaction, the mixture was cooled to room temperature, and the solid produced during the reaction was filtered and dissolved in chloroform to be treated with magnesium sulfate. The organic layer was distilled under reduced pressure and recrystallized with EtOH to obtain a yellow solid compound 1-D (7.96 g, 53%). MS [M] = 430

< Production Example  5> Synthesis of Compound of Formula 1-E

[Formula 1-E]

Under nitrogen atmosphere, the compound 1-C (11.6 g, 35 mmol) prepared in Preparation Example 3 was dissolved in chloroform (200 mL), NBS (6.25 g, 35 mmol) was added thereto, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, the solid produced during the reaction was filtered, washed with distilled water and dried to obtain the compound 1-E (5 g, 36%). MS [M] = 409

< Production Example  6> Synthesis of Compound of Formula 1-F

[Formula 1-F]

In a nitrogen atmosphere, Compound 1-D (7.96 g, 18.48 mmol) prepared in Preparation Example 4 was dissolved in chloroform (400 mL), followed by NBS (3.3 g, 18.48 mmol), followed by stirring at room temperature for 12 hours. After the reaction was completed, the solid produced during the reaction was filtered, washed with distilled water and dried to obtain the compound 1-F (5 g, 55%). MS [M] = 509

< Production Example  7> Synthesis of Compound of Formula 1-G

[Formula 1-G]

1-E (7.3 g, 17.9 mmol) prepared in Preparation Example 5 was completely dissolved in 150 mL of purified THF in a nitrogen atmosphere, and then tertiary-butyllithium (31.5 mL, 1.7 M pentane solution) at -78 ° C. Was added slowly. After stirring for one hour at the same temperature, trimethylborate (8 mL, 71.5 mmol) was added. The cold vessel was removed and the reaction mixture was stirred at room temperature for 3 hours. 2N aqueous hydrochloric acid solution (100 mL) was added to the reaction mixture, which was stirred for 1.5 hours at room temperature. The resulting precipitate was filtered off, washed successively with water and ethyl ether, and dried in vacuo. After drying, the mixture was dispersed in ethyl ether, stirred for 2 hours, filtered and dried to obtain a white compound (4.43 g, yield 71%) represented by Chemical Formula 1-G. MS: [M] = 374

< Production Example  8> Synthesis of Compound of Formula 1-H

[Formula 1-H]

The compound of Chemical Formula 1-H was prepared by the same method as the method of preparing Chemical Formula 1-G, except that Chemical Formula 1-F was used instead of Chemical Formula 1-E. MS: [M] = 474

< Production Example  9> Synthesis of Compound of Formula 2-A

[Formula 2-A]

Benzyl (2.1 g, 10 mmol), ammonium acetate (1.16 g, 15 mmol), aniline (4.67 g, 50 mmol), 4-bromo-benzaldehyde (1.85 g, 10 mmol) was acetic acid (20 mL ) Is suspended. The resulting mixture was stirred at 100 ° C. for about 6 hours and cooled to room temperature. After diluting the mixture with water (50 mL), the resulting solid was filtered, washed with water and ethyl ether to obtain the compound of formula 2-A (2.7 g, 62%). MS: [MH] ⁺ = 451

< Production Example  10> Synthesis of Compound of Formula 2-B

[Formula 2-B]

9,10-phenanthrenequinone (9,10-Phenanthrenequinone) (2.08 g, 10 mmol), ammonium acetate (1.16 g, 15 mmol), aniline (4.67 g, 50 mmol), 4-bromo-benzaldehyde (1.85 g, 10 mmol) was suspended in acetic acid (20 mL). The resulting mixture was stirred at 100 ° C. for about 6 hours and cooled to room temperature. After diluting the mixture with water (50 mL), the resulting solid was filtered and washed with water and ethyl ether (2.7 g, 62%). MS: [M] ⁺ = 449

< Production Example  11> Synthesis of Compound of Formula 2-C

[Formula 2-C]

Benzil (5 g, 23.8 mmol), ammonium acetate (2.75 g, 35.7 mmol), benzaldehyde (3.71 g, 23.7 mmol), 4-bromo-aniline (20.47 g, 119 mmol) was acetic acid (40 mL ) Is suspended. The resulting mixture was stirred at 100 ° C. for about 8 hours and cooled to room temperature. After diluting the mixture with water (100 mL), the resulting solid was filtered and washed with water and ethyl ether to give the compound of formula 2-C (5.9 g, 55%). MS: [M] ⁺ = 451

< Production Example  12> Synthesis of Compound of Formula 2-D

[Formula 2-D]

9,10-phenanthrenequinone (9,10-phenanthrenequinone) (4.95 g, 23.8 mmol), ammonium acetate (2.75 g, 35.7 mmol), benzaldehyde (3.71 g, 23.7 mmol), 4-bromo-aniline (20.47 g, 119 mmol) was suspended in acetic acid (40 mL). The resulting mixture was stirred at 100 ° C. for about 8 hours and cooled to room temperature. After diluting the mixture with water (100 mL), the resulting solid was filtered, washed with water and ethyl ether to give the compound of formula 2-D (5.9 g, 55%). MS: [M] ⁺ = 449

< Production Example  13> Synthesis of Compound of Formula 2-E

                             [Formula 2-E]

4-bromo-benzaldehyde (0.83 g, 4.5 mmol) was dispersed in 10 ml of nitrobenzene followed by N-phenyl-1,2-phenylenediamine (0.83 g, 4.5 mmol) was added and heated at 180 ° C for 6 h. After cooling to room temperature, nitro benzene was removed by distillation under reduced pressure, and then the obtained solid was filtered, washed with ethyl ether and dried under vacuum to obtain compound 2-E (0.94 g, 60%). MS: [M] = 349

< Production Example  14> Synthesis of Compound of Formula 2-F

                            [Formula 2-F]

Benzaldehyde (1.06 g, 10 mmol) was dispersed in 20 ml nitrobenzene, then N- (4-bromo-phenyl) -1,2-phenylenediamine (2.63 g, 10 mmol) was added and 6 Heat at 180 ^° C. for hours. After cooling to room temperature, nitrobenzene was removed by distillation under reduced pressure, and then the obtained solid was filtered, washed with ethyl ether and dried under vacuum to obtain compound 2-F (2.09 g, 60%). MS: [M] = 349

< Production Example  15> Synthesis of Compound of Formula 2-G

                          [Formula 2-G]

Benzaldehyde (1.06 g, 10 mmol) is dispersed in 20 ml nitrobenzene followed by addition of 5-bromo-2- (N-phenyl) -1,2-phenylenediamine (2.63 g, 10 mmol). And heated at 180 ° C. for 6 hours. After cooling to room temperature, nitro benzene was removed by distillation under reduced pressure, and then the obtained solid was filtered, washed with ethyl ether and dried under vacuum to obtain compound 2-G (1.74 g, 50%). MS: [M] = 349

< Production Example  16> Formula 2- H of  Synthesis of Compound

                                [Formula 2-H]

Under nitrogen atmosphere, 8-amino-7-quinolinecarbaldehyde (0.25 g, 1.45 mmol) and 4-bromoacetophenone (2.88 g, 1.45 mmol) were dispersed in 15 mL of EtOH Then, slowly add 0.5 mL of a solution of saturated KOH in EtOH. The resulting mixture was stirred at reflux for 15 hours. After cooling to rt, 20 mL of water was added and extracted with CH ₂ Cl ₂ (3 × 30 mL). The combined organic layers were dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with ethyl acetate and hexane to prepare the compound of Chemical Formula 2-H (0.194 g, 40%). MS: [M] = 335

< Production Example  17> Synthesis of Compound of Formula 2-I

                                 [Formula 2-I]

Under nitrogen atmosphere, 1-amino-2-naphthalenecarbaldehyde (0.25 g, 1.45 mmol) and 4-bromoacetophenone (2.88 g, 1.45 mmol) were dispersed in 15 mL of EtOH. Then, slowly add 0.5 mL of a solution of saturated KOH in EtOH. The resulting mixture was stirred at reflux for 15 hours. After cooling to room temperature, the resulting solid was filtered, washed with EtOH and dried in vacuo to give the compound of formula 2-I (0.290 g, 60%). MS: [M] = 334

< Production Example  18> the following formula 2- Of J  Synthesis of Compound

                             [Formula 2-J]

Isoamyl nitrite (0.54 mL, 4.1 mmol) was added to 50 mL of dichloroethane, and then anthraninic acid (0.51 g, 3.7 mmol) dissolved in 25 mL of dichloroethane was slowly added dropwise while stirring. This resulted in the reaction mixture of 4-bromo-benzaldehyde (0.68 g, 3.7 mmol) and aniline (0.344 g, 3.7 mmol) dispersed in 50 mL of dichloroethane. After the addition, the mixture was stirred to reflux. When the reaction solution turns from yellow to dark brown, it is cooled to room temperature. Dichloroethane was removed by distillation under reduced pressure, and purified by column chromatography using hexane / ethyl acetate mixed solution to obtain the compound of formula 2-J (0.716 g, 58%). MS: [M] = 334

< Production Example  19> Formula 2- K  Synthesis of Compound

                                    [Formula 2-K]

4-bromo-N-benzylideneaniline (2 brog-N-benzylideneaniline) (25.9 g, 0.1 mol) and benzamidine (24 g, 0.2 mol) were dissolved in 100 mL of chloroform and stirred under reflux for 24 hours. Let's do it. After cooling to room temperature, the resulting solid was filtered, washed with chloroform and dried to obtain the compound of formula 2-K (5.82 g, 15%). MS: [M] = 388

< Production Example  20> Synthesis of Compound of Formula 2-L

                                    [Formula 2-L]

Under nitrogen, benzaldehyde (1.06 g, 10 mmol) and acetophenone (1.2 g, 10 mmol) were dispersed in 20 mL of ethanol, 1 mL of a solution of sodium methoxide 1N dissolved in methanol was added, followed by stirring at room temperature for 5 hours. It was. After further stirring for 4 hours, 4-bromobenzeneamidine (1.2 g, 6 mmol) and sodium hydroxide (0.8 g, 20 mmol) were added, and the mixture was stirred under reflux for 5 hours. After cooling to room temperature, the resulting solid was filtered and purified by column chromatography to give the formula 2-L (1.2g 30%). MS: [M] = 387

< Example  1> Synthesis of Compound of Formula 1-11

[Formula 1-11]

After completely dissolving the compound of Formula 1-G (2.35 g, 6.3 mmol) and the compound of Formula 2-A (2.84 g, 6.3 mmol) in tetrahydrofuran (100 mL), an aqueous 2M potassium carbonate solution (20 mL) was added. Tetrakistriphenyl-phosphinopalladium (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 1-11 (3.1 g, 70%). MS: [M] ⁺ = 700

< Example  2> Synthesis of Compound of Formula 1-12

[Formula 1-12]

After completely dissolving the compound of Formula 1-H (3.0 g, 6.3 mmol) and the compound of Formula 2-A (2.84 g, 6.3 mmol) in tetrahydrofuran (100 mL), an aqueous 2M potassium carbonate solution (20 mL) was added. Tetrakistriphenyl-phosphinopalladium (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 1-12 (3.3 g, 65%). MS: [M + H] ⁺ = 800

< Example  3> Synthesis of Compound of Formula 1-128

[Formula 1-128]

The compound of Chemical Formula 1-128 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-B was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 798

< Example  4> Synthesis of Compound of Formula 2-12

[Formula 2-12]

The compound of Chemical Formula 1-12 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-C was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 800

< Example  5> Synthesis of Compound of Formula 2-128

[Formula 2-128]

The compound of Chemical Formula 2-128 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-D was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 798

< Example  6> Synthesis of Compound of Formula 3-12

[Formula 3-12]

The compound of Chemical Formula 3-12 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-E was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 698

< Example  7> Synthesis of Compound of Formula 4-12

[Formula 4-12]

The compound of Chemical Formula 4-12 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-F was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 698

< Example  8> Synthesis of Compound of Formula 5-2

[Formula 5-2]

The compound of Chemical Formula 5-2 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-G was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 698

< Example  9> Synthesis of Compound of Formula 6-2

[Formula 6-2]

After dissolving the compound of Formula 1-H (3.0 g, 6.3 mmol) and 2-chloro-1,10-phenanthroline (1.35 g, 6.3 mmol) in tetrahydrofuran (100 mL), 2M potassium carbonate solution ( 20 mL) was added and tetrakistriphenyl-phosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by stirring for 5 hours. The temperature was lowered to room temperature and the resulting solid was filtered, washed with water and ethanol, and dried to prepare the compound of Chemical Formula 6-2 (2.3 g, 60%). MS: [M] ⁺ = 608

< Example  10> Synthesis of Compound of Formula 6-5

[Formula 6-5]

The compound of Chemical Formula 6-5 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-H was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 684

< Example  11> Synthesis of Compound of Formula 6-16

[Formula 6-16]

The compound of Formula 1-H (3.0 g, 6.3 mmol) and 2-chlorobenzo [h] quinoline (1.35 g, 6.3 mmol) were completely dissolved in tetrahydrofuran (100 mL), followed by 2M aqueous potassium carbonate solution (20 mL). Tetrakistriphenyl-phosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature and the resulting solid was filtered, washed with water and ethanol, and dried to prepare the compound of Chemical Formula 6-16 (2.3 g, 60%). MS: [M] ⁺ = 607

< Example  12> Synthesis of Compound of Formula 6-19

[Formula 6-19]

The compound of Chemical Formula 6-19 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-I was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 683

< Example  13> Synthesis of Compound of Formula 7-2

[Formula 7-2]

The compound of Formula 1-H (3.0 g, 6.3 mmol) and 9-chlorophenanthridine (1.35 g, 6.3 mmol) were completely dissolved in tetrahydrofuran (100 mL), followed by adding 2M aqueous potassium carbonate solution (20 mL). Tetrakistriphenyl-phosphinopalladium (155 mg, 0.013 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the resulting solid was filtered, washed with water and ethanol, and dried to prepare the compound of Chemical Formula 7-2 (1.91 g, 50%). MS: [M] ⁺ = 607

< Example  14> Synthesis of Compound of Formula 7-5

[Formula 7-5]

The compound of Chemical Formula 7-5 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-J was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 683

< Example  15> Synthesis of Compound of Formula 8-5

[Formula 8-5]

The compound of Chemical Formula 8-5 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-K was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 737

< Example  16> Synthesis of Compound of Formula 8-11

[Formula 8-11]

The compound of Chemical Formula 8-11 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 2-L was used instead of Chemical Formula 2-A. MS: [M] ⁺ = 736

< 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. In this case, Fischer Co. product was used as the detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. 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), which is a substance for transporting holes on the hole injection layer, is vacuum deposited to form a hole transport layer Formed.

[NPB]

Subsequently, the light emitting layer was formed by vacuum depositing the following GH and GD with a film thickness of 20: 1 on the hole transport layer at a film thickness of 300 m 3.

         [GH] [GD]

The compound of Formula 1-11 prepared in Example 1 was vacuum deposited to a thickness of 200 kPa on the light emitting layer to form an electron injection and transport layer.

The cathode was formed by sequentially depositing lithium fluoride (LiF) and aluminum at a thickness of 2000 2000 on the electron injection and transport layer sequentially.

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 2 Å / sec, the vacuum degree during deposition was 2 × 10 ⁻⁷ to 5 × 10 ⁻⁸ torr was maintained.

As a result of applying a forward electric field of 5.2 V to the organic light emitting device, green light was observed at 17 mA / cm2 at a current density of 5 mA / cm 2.

< Experimental Example  2>

An organic EL device was manufactured in the same manner as in Experiment 1, except that the compound of Formula 1-12 was used instead of the compound of Formula 1-11.

As a result of applying a forward electric field of 4.6 V to the organic light emitting device, green light was observed at 18 mA / cm at a current density of 5 mA / cm 2.

< Experimental Example  3>

An organic EL device was manufactured in the same manner as in Experiment 1, except that the compound of Formula 2-12 was used instead of the compound of Formula 1-11.

As a result of applying a forward electric field of 4.0 V to the organic light emitting device prepared above, green light was observed at 20 mA / cm 2 at a current density of 5 mA / cm 2.

< Experimental Example  4>

An organic EL device was manufactured in the same manner as in Experiment 1, except that a compound of Formula 3-12 was used instead of a compound of Formula 1-11.

As a result of applying a forward electric field of 4.8 V to the organic light emitting device, green light was observed at 17 mA / cm2 at a current density of 5 mA / cm 2.

< Experimental Example  5>

An organic EL device was manufactured in the same manner as in Experiment 1, except that the compound of Formula 4-12 was used instead of the compound of Formula 1-11.

As a result of applying a forward electric field of 4.1 V to the organic light emitting device, green light was observed at 19 mA / cm at a current density of 5 mA / cm 2.

< Experimental Example  6>

An organic EL device was manufactured in the same manner as in Experiment 1, except that a compound of Formula 5-12 was used instead of a compound of Formula 1-11.

As a result of applying a forward electric field of 3.9 V to the organic light emitting device, green light was observed at 20 mA / cm 2 at a current density of 5 mA / cm 2.

< Experimental Example  7>

An organic EL device was manufactured in the same manner as in Experiment 1, except that a compound of Formula 6-5 was used instead of a compound of Formula 1-11.

As a result of applying a forward electric field of 4.1 V to the organic light emitting device prepared above, green light was observed at 25 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  8>

An organic EL device was manufactured in the same manner as in Experiment 1, except that a compound of Formula 6-16 was used instead of a compound of Formula 1-11.

As a result of applying a forward electric field of 4.5 V to the organic light emitting device prepared above, green light was observed at 19 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  9>

An organic EL device was manufactured in the same manner as in Experiment 1, except that a compound of Formula 7-5 was used instead of a compound of Formula 1-11.

As a result of applying a forward electric field of 4.3 V to the organic light emitting device, green light was observed at 17 mA / cm2 at a current density of 5 mA / cm 2.

< Experimental Example  10>

An organic EL device was manufactured in the same manner as in Experiment 1, except that a compound of Formula 8-5 was used instead of a compound of Formula 1-11.

As a result of applying a forward electric field of 4.8 V to the organic light emitting device, green light was observed at 19 mA / cm at a current density of 5 mA / cm 2.

< Comparative example  1>

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), GH: GD (film thickness ratio 20: 1) (300 kPa) and electron transport material (200 kPa) represented by the following chemical formula disclosed in Korean Patent Laid-Open Publication No. 2003-0067773, lithium fluoride (LiF) 12 kPa Were sequentially vacuumed to form a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. 2000 nm thick aluminum was deposited thereon to form a cathode to manufacture an organic light emitting device.

[Electron transport material]

As a result of applying a forward electric field of 4.8 V to the organic light emitting device, green light was observed to be 18 cd / A at a current density of 5 mA / cm 2.

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

2 is an MS graph of a compound of Formulas 2-12 of the present invention.

<Explanation of symbols for the main parts of the drawings>

1 substrate 2 anode

3 hole injection layer 4 hole transport layer

5 organic light emitting layer 6 electron transport layer

7 cathode

Claims (26)

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 ~ C ₄₀ cycloalkyl group, C ₂ ~ C ₄₀ of the heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted carbazolyl group, and a C ₅ ~ least one selected from the heteroaryl group consisting of C ₄₀ of C ₆ ~ C ₄₀ aryl group unsubstituted or substituted with a 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 ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ 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 ₂ ~ C ₄₀ A fluorenyl 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 ₅ -C ₄₀ heteroaryl group; 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 ₂ ~ C _Is selected from the group consisting of an amino group unsubstituted or substituted with at least one group selected from the group consisting of ₄₀ heterocycloalkyl groups, C ₆ -C ₄₀ aryl groups and C ₅ -C ₄₀ heteroaryl groups, R3 is a group represented by any one of the following Formulas 2 to 9,

 [Formula 2] [Formula 3] [Formula 4]

 [Formula 5] [Formula 6] [Formula 7]

 [Formula 8] [Formula 9] In Chemical Formulas 2 to 9, X and Y are each CH or N, R11 to R24 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 ₂ ~ 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 ₅ -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 ₂ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl 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 ₅ -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 ₂ ~ C ₄₀ A C ₂ -C ₄₀ alkenyl group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -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 ₂ ~ C ₄₀ A C ₁ to C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to 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 ₂ ~ C ₄₀ An 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 ₅ -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 ₂ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or 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 ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of a group is selected from the group consisting of a heteroaryl unsubstituted C ₅ ~ C ₄₀ of Can and R11 and R12, and R14 and R15 may be connected to each other to form a condensed ring, In Formula 9, when Y is CH, it may be connected to R23 or R24 group to form a condensed ring. L ₁ to L ₈ are direct bonds; 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 a C ₅ ~ 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 ₂ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more 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 ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; 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 ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ the aryl group and the C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C ₄₀ arylamine 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 ₂ ~ C ₄₀ A C ₂₅ -C ₄₀ spiro 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 ₅ -C ₄₀ heteroaryl group; 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 ₂ ~ C Selected from the group consisting of C ₂₅ -C ₄₀ open spiro groups unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl groups, C ₆ -C ₄₀ aryl groups and C ₅ -C ₄₀ heteroaryl groups Become, R4 to R10 are each independently 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 ₂ ~ 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 ₅ -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 ₂ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl 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 ₅ -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 ₂ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or 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 ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or 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 ₂ 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 ₅ ~ 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 of claim 1, wherein R 1 and R 2 in Formula 1 are the same heteroaryl group. The anthracene derivative according to claim 1, wherein R 1 and R 2 of Formula 1 are amino groups substituted with the same aryl group or heteroaryl group. The anthracene derivative according to claim 1, wherein R 1 and R 2 of Formula 1 are selected from the group consisting of

Z 1 to Z 3 in the formula 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 ₂ ~ 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 ₅ -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 ₂ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl 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 ₅ -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 ₂ ~ C ₄₀ A C ₂ -C ₄₀ alkenyl group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -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 ₂ ~ C ₄₀ A C ₁ to C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to 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 ₂ ~ C ₄₀ An 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 ₅ -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 ₂ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or 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 ₂ ~ C ₄₀ heterocycloalkyl group of, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or are selected from the group consisting of a heteroaryl unsubstituted C ₅ ~ C ₄₀ . The anthracene derivative according to claim 1, wherein L ₁ to L ₈ are each independently a direct bond or selected from the group consisting of the following formulas.

The anthracene derivative according to claim 1, wherein R 3 of Formula 1 is represented by Formula 2, R 4 to R 10 are hydrogen, and R 1, R 2, L ₁ , and R 11 to R 13 are represented by the following formulas. :

The anthracene derivative according to claim 1, wherein the anthracene derivative represented by Formula 1 includes a compound represented by the following Formula:

The anthracene derivative according to claim 1, wherein R3 of Formula 1 is represented by Formula 3, R4 to R10 are hydrogen, and R1, R2, L ₂ and R14 to R16 are represented by the following formulas:

The anthracene derivative according to claim 1, wherein the anthracene derivative represented by Chemical Formula 1 includes a compound represented by the following chemical formula.

The anthracene derivative according to claim 1, wherein R 3 of Formula 1 is represented by Formula 4, R 4 to R 10 are hydrogen, and R 1, R 2, L ₃ , R 17, and R 18 are represented by the following formulas.

The anthracene derivative according to claim 1, wherein R 3 of Formula 1 is represented by Formula 5, R 4 to R 10 are hydrogen, and R 1, R 2, L ₄ , R 19, and R 20 are represented by the following formulas.

The anthracene derivative according to claim 1, wherein R 3 of Formula 1 is represented by Formula 6, R 4 to R 10 are hydrogen, and R 1, R 2, L ₅ , R 21, and R 22 are represented by the following formulas.

The anthracene derivative according to claim 1, wherein the anthracene derivative represented by Chemical Formula 1 includes a compound represented by the following chemical formula.

The anthracene derivative according to claim 1, wherein the anthracene derivative represented by Chemical Formula 1 includes a compound represented by the following chemical formula.

The anthracene derivative according to claim 1, wherein the anthracene derivative represented by Chemical Formula 1 includes a compound represented by the following chemical formula.

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 anthracene according to any one of claims 1 to 16. Organic electronic device comprising a derivative. The organic electronic device of claim 17, 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 17, wherein the organic electronic device is an organic light emitting device. The organic electronic device of claim 19, 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 19, 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 electronic device of claim 19, wherein the organic material layer of the organic light emitting device includes a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and / or transport layer. The organic electronic device of claim 19, wherein the organic material layer of the organic light emitting device includes a light emitting layer, and the light emitting layer includes the anthracene derivative. The organic electronic device of claim 19, wherein the organic material layer of the organic light emitting device includes an electron transport and / or injection layer, and the layer includes the anthracene derivative. The organic electronic device of claim 19, wherein the organic material layer of the organic light emitting device includes a layer for simultaneously transporting holes and emitting light. The organic electronic device of claim 19, wherein the organic material layer of the organic light emitting device includes a layer for simultaneously emitting light and transporting electrons.

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