KR101317531B1 - New imidazole derivatives and organic electronic device using the same - Google Patents

Abstract

The present invention provides a novel imidazole derivative and an organic electronic device using the same. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and lifetime.

Imidazole, anthracene, organic electronic device, organic light emitting device

Description

Novel imidazole derivatives and organic electronic devices using the same {NEW IMIDAZOLE DERIVATIVES AND ORGANIC ELECTRONIC DEVICE USING THE SAME}

The present invention relates to a novel imidazole derivative having an anthracene group bonded to an imidazole 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 that injects holes and / or electrons into an organic semiconductor material layer that interfaces with the electrode by applying a voltage or current to two or more electrodes, and operates by 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, but in the organic electronic devices, the electron / hole injecting material, the electron / hole extracting material, the electron / hole transporting material, or the light emitting material all have a similar principle.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic layer between them. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected into the anode, electrons are injected into the organic layer, electrons are injected into the organic layer, excitons are formed when injected holes and electrons meet, When it falls to a state, it becomes a light. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, 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 light emitting material can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent 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 is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the organic light emitting device, a material constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material is supported by a stable and efficient material Should 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 Flavon derivatives or Chiso's germanium and silicon chloropetadiene derivatives are known. (Japanese Patent Laid-Open No. 1998-017860, Japanese Patent Laid-Open No. 1999-087067) ).

In addition, the organic monomolecular substance includes PBD (2-biphenyl-4-yl-5- (4-t-butylphenyl) -1,3,4-oxadiazole) derivative coupled 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.

Organic light emitting devices using the organic single molecular material as an electron transporting layer have short lifetime, low storage durability and low reliability. These problems are caused by physical or chemical changes of organic materials, photochemical or electrochemical changes of organic materials, oxidation and peeling of the cathodes, 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 continuing need for the development of new materials having improved luminescence brightness, luminescence efficiency, and lifetime, as compared with organic EL devices using such compounds.

Thus, the present inventors have found an imidazole derivative having a novel structure to which an anthracene group is bound. In addition, it has been found that the formation of an organic material layer of an organic electronic device using the novel imidazole derivative may have the effect of increasing the efficiency of the device, lowering the driving voltage, extending the life, and increasing the stability.

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

The present invention provides novel imidazole derivatives.

In addition, 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, at least one of the organic layer is the novel imidazole It provides an organic electronic device comprising a derivative.

The novel imidazole derivatives according to the present invention are introduced with various anthracene substituents, and can be used as organic material layers of organic electronic devices including organic light emitting devices, and organic electronic devices including organic light emitting devices using the same have increased efficiency and driving voltage. It shows excellent characteristics in falling, extending life and increasing stability.

The novel imidazole derivatives according to the invention are characterized in that the compounds represented by the following formula (1).

In 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 and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or unsubstituted 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 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 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 _It 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 group, C ₆ ~ C ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group,

At least one of R3 to R10 is a group represented by the following formula (2) or formula (3),

In Chemical Formulas 2 and 3,

R11 to R16 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 a group is selected from the group consisting of a heteroaryl unsubstituted C ₅ ~ C ₄₀ of Can and

L ₁ and L ₂ 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 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 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 heteroaryl group substituted with one or more groups selected from the group consisting of 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 C ₂₅ ~ C ₄₀ open spiro 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 ₅ ~ C ₄₀ heteroaryl group ,

R3 to R10 other than the group represented by the formula (2) or (3) is 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 C ₃ ~ C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and 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 imidazole derivative represented by Formula 1, R1 and R2 are preferably the same aryl group. The aryl group is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, and the like.

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

In addition, in the imidazole derivative represented by the 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 imidazole 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 A C ₁ -C ₄₀ alkyl 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 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 be.

Two or more selected from R 11, R 12, and R 13 in Formula 2; And at least two selected from R 14, R 15, and R 16 in Formula 3 are the same aryl group.

Two or more selected from R 11, R 12, and R 13 in Formula 2; And at least two selected from R 14, R 15 and R 16 in Formula 3 are the same heteroaryl group.

Two or more selected from R 11, R 12, and R 13 in Formula 2; And at least two selected from R 14, R 15, and R 16 in Formula 3 are amino groups substituted with the same aryl group or heteroaryl group.

At least one of R 11, R 12 and R 13 in Formula 2; And at least one of R 14, R 15 and R 16 in Formula 3 is hydrogen.

R11, R12, and R13 of Chemical Formula 2; And R14, R15 and R16 of the formula (3) is preferably selected from the group consisting of alkyl groups.

L ₁ and L ₂ in Formula 2 is preferably a direct bond or selected from the group consisting of the following formula.

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

It is preferable that the alkyl group does not cause steric hindrance of 1 to 40 carbon atoms. 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 does not give a steric hindrance of 3 to 40 carbon atoms. Specifically, there are cyclopentyl group, cyclohexyl group, and the like, but is not limited thereto.

The alkenyl group is preferably an alkenyl group having 2 to 40 carbon atoms, and in particular, an alkenyl group in which an aryl group such as a stylbenyl group or a styrenyl group is substituted, 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, isoquinoline group, and the like. It is not limited only to these.

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

등이 있으나, 이에 한정되는 것은 아니다.Spiro is a structure in which two ring organic compounds are connected to one atom,

And the like, but the present invention is not limited thereto.

등이 있으나, 이에 한정되는 것은 아니다.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.

And the like, but the present invention 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.

The novel imidazole derivatives according to the present invention are preferably selected from compounds represented by the following formulas 4 to 7, but are not limited thereto:

In Formulas 4 to 7, wherein R1 to R16, L ₁ and L ₂ are as defined in the formula (1).

The imidazole derivatives represented by Formulas 4 to 7 are specifically illustrated in Tables 1 to 4 below.

Specifically, the compound represented by Formula 4 includes a compound represented by the formula of Table 1 below, wherein R3 to R10 are hydrogen:

Specifically, the compound represented by Formula 5 includes a compound represented by the formula of Table 2 wherein R 3 to R 10 are hydrogen:

Specifically, the compound represented by Formula 6 includes a compound represented by the formula of Table 3 below, wherein R3 to R10 are hydrogen:

Specifically, the compound represented by Formula 7 includes a compound represented by the formula of Table 4 wherein R3 to R10 are hydrogen:

Hereinafter, the manufacturing method of the novel imidazole derivative which concerns on this invention is demonstrated.

The novel imidazole derivative represented by Chemical Formula 1 may be prepared by introducing an anthracene substituent to the imidazole derivative. Specifically, the compound of Formula 1 is prepared by Suzuki bond reaction of 2-anthracene boronic acid or 2-anthracene boron ester derivative with an aryl halide derivative under a Pd catalyst, and an anthraquinone derivative prepared as a dialcohol derivative, followed by reduction. can do.

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

Specifically, the anthracene substituent in the imidazole derivative represented by Formula 1

1) preparing an anthraquinone derivative substituted with R9 by suzuki bonding an anthraquinone derivative substituted with a halogen group and a boronic acid or boron ester compound having an R9 substituent under a Pd catalyst,

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

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

In Scheme 1, R1 to R10 are the same as defined in Chemical Formula 1.

In addition, the anthracene substituent in the imidazole derivative represented by 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) It may also be prepared by a method comprising the step of Suzuki bonding the anthracene boron ester derivative prepared in step 3) and a halide of R9 under a Pd catalyst. Such a manufacturing method may be represented by the following Scheme 2.

In Scheme 2, R1 to R10 are the same as defined in Chemical Formula 1.

In addition, a method for preparing an imidazole derivative represented by Formulas 2 to 3 will be described.

The imidazole derivative represented by Formula 2 may be prepared by introducing an amine substituent into the ethanedione derivative. Specifically, the imidazole derivative represented by Formula 2 may be prepared under an acid catalyst using a derivative in which a halide element and an aldehyde are substituted, ammonium acetate (NH ₄ OAc), an amine derivative, and an ethanedione derivative.

The reaction used when preparing the imidazole derivative represented by Chemical Formula 2 may use a general method known in the art.

Specifically, the imidazole derivative represented by Chemical Formula 2 is prepared under an acid catalyst by mixing an L ₁ derivative having a halogen group and an aldehyde group and an ethanedione derivative having an R 11 and R 12 substituent, an ammonium acetate, and an amine derivative having an R 13 substituent. It may be prepared by a manufacturing method comprising the step.

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

In Scheme 3, R11 to R13 and L ₁ are as defined in Chemical Formula 1.

In addition, the imidazole derivative represented by Chemical Formula 3 may be prepared under an acid catalyst using an amine derivative, an ammonium acetate, an aldehyde derivative, or an ethanedione derivative substituted with a halide element.

The reaction used when preparing the imidazole derivative represented by Chemical Formula 3 may use a general method known in the art.

Specifically, the imidazole derivative represented by Formula 3 is prepared under an acid catalyst by mixing a halide element with an amine derivative having an L ₂ derivative, an ethanedione derivative having an R14 and R15 substituent, an ammonium acetate, an aldehyde derivative having an R16 substituent, and the like. It may be prepared by a manufacturing method comprising the step.

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

In Reaction Scheme 4, R14 to R16 and L ₂ are the same as defined in Chemical Formula 1.

In addition, 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, at least one of the organic layer is represented by the formula (1) It provides an organic electronic device comprising an imidazole derivative.

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, the organic light emitting device will be described.

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 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. The organic light emitting device having the structure as shown in FIG. 1 is generally referred to as an organic light emitting device having a normal structure. However, the present invention is not limited to this 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 imidazole 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, electrons It may be included in the transport layer, electron transport and / or injection layer. 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 manufactured using a conventional organic light emitting device manufacturing method and materials, except that the imidazole derivative represented by Formula 1 is used in at least one layer of the organic material layer of the 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, 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 material layer may be formed by using a variety of polymer materials in a smaller number of layers by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process, Can be manufactured.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode 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), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

The negative electrode material is preferably 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

As the hole transporting material, a material having high mobility to holes is suitable for transporting holes from the anode or the hole injection layer to the light emitting layer. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; Bis-methyl-8-hydroxyquinoline paraphenylphenol aluminum complex (Balq); 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing 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 front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The novel imidazole 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 photoconductors, organic transistors, and the like.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention, whereby the scope of the invention is not limited.

Preparation Example 1 Synthesis of Compound of Formula 1-A

[Chemical Formula 1-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). To the suspension was added palladium (diphenylphosphinoferrocene) chloride (0.24 g, 3 mol%). 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 1-A (5.46 g, 92%) which was 9,10-dinaphthylanthracenyl-2-borate.

MS: [M + H] ⁺ = 557

Preparation Example 2 Synthesis of Compound of Formula 1-B

[Chemical Formula 1-B]

1-bromonaphthalene (34.8 g, 168.2 mmol) was dissolved in tetrahydrofuran (170ml), the temperature was lowered to -78 ° C, n-butyllithium (67.3 ml, 168.2 mmol) was slowly added, followed by stirring for 1 hour. . 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 gave the compound of Chemical Formula 1-B (32.3 g, 82%).

MS: [M + H] ⁺ = 544

Preparation Example 3 Synthesis of Compound of Formula 1-C

[Chemical Formula 1-C]

The compound of Chemical Formula 1-B (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 1-C (25.5 g, 84%).

MS: [M + H] ⁺ = 509

Preparation Example 4 Synthesis of Compound of Formula 1-D

[Chemical Formula 1-D]

Method of synthesizing the compound of Formula 1-A except that the compound of Formula 1-C was used instead of 2-bromo-9,10-dinaphthylanthracene in the synthesis of the compound of Formula 1-A of Preparation Example 1 Synthesis was performed in the same manner as to prepare a compound of Formula 1-D.

MS: [M + H] ⁺ = 557

Preparation Example 5 Synthesis of Compound of Formula 1-E

[Chemical Formula 1-E]

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 then 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 in vacuo to prepare the compound of formula 1-E (1.6g, 25%) as a white solid.

MS: [M + H] ⁺ = 322

Preparation Example 6 Synthesis of Compound of Formula 1-F

[Chemical Formula 1-F]

The compound of Formula 1-E (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, a compound of formula 1-F (3.32 g, 73%) was prepared as a dialcohol compound.

MS [M + H] ⁺ = 773

Preparation Example 7 Synthesis of Compound of Formula 1-G

[Chemical Formula 1-G]

The compound of formula 1-F (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 1-G (2.87 g, 90%).

MS: [M + H] ⁺ = 739

Preparation Example 8 Synthesis of Compound of Formula 1-H

[Chemical Formula 1-H]

Except for using the compound of Formula 1-G instead of 2-bromo-9,10-dinaphthylanthracene and bis (pinacolato) diboron in the method for preparing the compound of Formula 1-A of Preparation Example 1 Was prepared in the same manner as the method for preparing the compound of Formula 1-A.

MS [M + H] ⁺ = 787

Preparation Example 9 Synthesis of Compound of Formula 1-I

[Formula I-I]

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 diluted with 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 1-I (2.7 g, 62%).

MS: [M + H] ⁺ = 452

Preparation Example 10 Synthesis of Compound of Formula 1-J

[Chemical Formula 1-J]

The compound of Chemical Formula 1-J was prepared by the same method as the method of preparing Chemical Formula 1-I, except that 3-bromo-benzaldehyde was used instead of 4-bromo-benzaldehyde.

MS: [M + H] ⁺ = 452

Preparation Example 11 Synthesis of Compound of Formula 1-K

[Formula 1-K]

The compound of Chemical Formula 1-K was prepared by the same method as the method of preparing Chemical Formula 1-I, except that β-naphthyl was used instead of benzyl.

MS: [M + H] ⁺ = 552

Preparation Example 12 Synthesis of Compound of Formula 1-L

[Formula 1-L]

The compound of Formula 1-L was prepared by the same method as the method of preparing Formula 1-I, except that 2-amino-naphthalene was used instead of aniline.

MS: [M + H] ⁺ = 502

Example 1 Synthesis of Compound of Formula 1-12

[Formula 1-12]

After completely dissolving the compound of Formula 1-A (3.5 g, 8.0 mmol) and the compound of Formula 1-I (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] ⁺ = 802

Example 2 Synthesis of Compound of Formula 1-13

[Formula 1-13]

The compound of Chemical Formula 1-13 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 1-D was used instead of Chemical Formula 1-A.

MS: [M + H] ⁺ = 802

Example 3 Synthesis of Compound of Formula 1-15

[Chemical Formula 1-15]

The compound of Chemical Formula 1-15 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 1-H was used instead of Chemical Formula 1-A.

MS: [M + H] ⁺ = 1032

Example 4 Synthesis of Compound of Formula 1-22

[Formula 1-22]

The compound of Chemical Formula 1-22 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 1-J was used instead of Chemical Formula 1-I.

MS: [M + H] ⁺ = 802

Example 5 Synthesis of Compound of Formula 1-55

[Formula 1-55]

The compound of Chemical Formula 1-55 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 1-K was used instead of Chemical Formula 1-I.

MS: [M + H] ⁺ = 902

Example 6 Synthesis of Compound of Formula 1-91

[Formula 1-91]

The compound of Chemical Formula 1-91 was prepared by the same method as the method of preparing Chemical Formula 1-12, except that Chemical Formula 1-L was used instead of Chemical Formula 1-I.

MS: [M + H] ⁺ = 852

Preparation Example 13 Synthesis of Compound of Formula 2-A

[Chemical Formula 2-A]

Benzyl (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, washed with water and ethyl ether to give the compound of formula 2-A (5.9 g, 55%).

MS: [M + H] ⁺ = 452

Preparation Example 14 Synthesis of Compound of Formula 2-B

[Chemical Formula 2-B]

The compound of Chemical Formula 2-B was prepared by the same method as the method of preparing Chemical Formula 2-A, except that 3-bromo-aniline was used instead of 4-bromo-aniline.

MS: [M + H] ⁺ = 452

Preparation Example 15 Synthesis of Compound of Formula 2-C

[Chemical formula 2-C]

The compound of Chemical Formula 2-C was prepared by the same method as the method of preparing Chemical Formula 2-A, except that β-naphthyl was used instead of benzyl.

MS: [M + H] ⁺ = 552

Preparation Example 16 Synthesis of Compound of Formula 2-D

[Chemical Formula 2-D]

The compound of Chemical Formula 2-D was prepared by the same method as the method of preparing Chemical Formula 2-A, except that 2-naphthalenealdehyde was used instead of benzaldehyde.

MS: [M + H] ⁺ = 502

Preparation Example 17 Synthesis of Compound of Formula 2-E

The compound of Formula 2-E was prepared by the same method as the method of preparing Formula 2-A, except that 2-pyridinealdehyde was used instead of benzaldehyde.

MS: [M + H] ⁺ = 453

Example 7 Synthesis of Compound of Formula 2-12

[Formula 2-12]

After completely dissolving the compound of Formula 1-A (3.5 g, 8.0 mmol) and the compound of Formula 2-A (2.84 g, 6.3 mmol) in tetrahydrofuran (100 mL), 2M aqueous 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 2-12 (2.8 g, 55%).

MS: [M] ⁺ = 800.3

Example 8 Synthesis of Compound of Formula 2-13

[Formula 2-13]

The compound of Chemical Formula 2-13 was prepared by the same method as the method of preparing Chemical Formula 2-12, except that Chemical Formula 1-D was used instead of Chemical Formula 1-A.

MS: [M + H] ⁺ = 802

Example 9 Synthesis of Compound of Formula 2-22

The compound of Chemical Formula 2-22 was prepared by the same method as the method of preparing Chemical Formula 2-12, except that Chemical Formula 2-B was used instead of Chemical Formula 2-A.

MS: [M + H] ⁺ = 802

Example 10 Synthesis of Compound of Formula 2-55

The compound of Chemical Formula 2-55 was prepared by the same method as the method of preparing Chemical Formula 2-12, except that Chemical Formula 2-C was used instead of Chemical Formula 2-A.

MS: [M + H] ⁺ = 902

Example 11 Synthesis of Compound of Formula 2-91

[Formula 2-91]

The compound of Chemical Formula 2-91 was prepared by the same method as the method of preparing Chemical Formula 2-12, except that Chemical Formula 2-D was used instead of Chemical Formula 2-A.

MS: [M + H] ⁺ = 852

Example 12 Synthesis of Compound of Formula 2-118

The compound of Chemical Formula 2-118 was prepared by the same method as the method of preparing Chemical Formula 2-12, except that Chemical Formula 2-E was used instead of Chemical Formula 2-A.

MS: [M + H] ⁺ = 803

Preparation Example 18 Synthesis of Compound of Formula 3-A

2,6-diaminoanthraquinone (23.8 g, 100 mmol) was dispersed in an aqueous solution of hydrogen bromide at a concentration of 48 wt%, and sodium nitrite (NaNO ₂ , 14.1 g; 204 mmol) was slowly added at 20 ° C. After gas evolution, a solution of copper bromide (CuBr, 29.5 g; 206 mmol) in 48 wt% aqueous hydrogen bromide solution (63 mL) was slowly added with a small amount of ethanol (50 mL). The temperature of the reaction was slowly raised to room temperature and then refluxed for one hour. After cooling to room temperature, water was added, and the resulting precipitate was filtered, washed with water, and dried in vacuo. The obtained solid was dissolved in chloroform, passed through silica gel, and the solvent was removed under reduced pressure. After separation by column chromatography, and recrystallized with chloroform to give the compound of formula 3-A (10 g, yield 27%) of light yellow.

The analysis results of this compound are as follows.

1 H NMR (300 MHz, CDCl ₃ ), 8.44 (d, J = 2.1 Hz, 2H), 8.18 (d, J = 8.0 Hz, 2H), 7.95 (dd, J = 2.1, 8.0 Hz, 2H.)

MS: [M + H] ⁺ = 367

Preparation Example 19 Synthesis of Compound of Formula 3-B

[Formula 3-B]

The compound of Chemical Formula 3-B was prepared by the same method as the method of preparing Chemical Formula 2-B, except that Chemical Formula 3-A was used instead of 2-bromoanthraquinone.

MS: [M + H] ⁺ = 623

Preparation Example 20 Synthesis of Compound of Formula 3-C

[Formula 3-C]

The compound of Chemical Formula 3-C was prepared by the same method as the method of preparing Chemical Formula 1-C, except that Chemical Formula 3-B was used instead of Chemical Formula 1-B.

MS: [M + H] ⁺ = 589

PREPARATION EXAMPLE 21 Synthesis of Compound of Formula 3-D

[Formula 3-D]

Method for synthesizing the compound of Formula 1-A, except that Formula 1-I was used instead of 2-bromo-9,10-dinaphthylanthracene in the synthesis of Compound 1-A of Preparation Example 1 Synthesis was carried out in the same manner as to prepare a compound of Formula 3-D.

MS: [M + H] ⁺ = 499

Preparation Example 22 Synthesis of Compound of Formula 3-E

[Formula 3-E]

Method of synthesizing the compound of Formula 1-A except that the compound of Formula 1-J was used instead of 2-bromo-9,10-dinaphthylanthracene in the synthesis of the compound of Formula 1-A of Preparation Example 1 Synthesis was performed in the same manner as to prepare a compound of Formula 3-E.

MS: [M + H] ⁺ = 499

Example 13 Synthesis of Compound of Formula 3-12

(3-12)

After completely dissolving the compound of Formula 3-C (5.9 g, 10.0 mmol) and the compound of Formula 3-D (10.5 g, 21.0 mmol) in tetrahydrofuran (100 mL), 2M aqueous potassium carbonate solution (50 mL) was added. Tetrakistriphenylphosphinopalladium (231 mg, 0.02 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: 1 to prepare the compound of Chemical Formula 3-12 (5.9 g, 50%).

MS: [M + H] ⁺ = 1172

Example 14 Synthesis of Compound of Formula 3-22

Synthesis of the compound of Chemical Formula 3-12 in Preparation Example 3, except that Chemical Formula 3-E was used instead of Chemical Formula 3-D. The compound of 3-22 was prepared.

MS: [M + H] ⁺ = 1172

Preparation Example 23 Synthesis of Compound of Formula 4-A

In the same manner as in the synthesis of the compound of Formula 1-A, except that in the synthesis of the compound of Formula 1-A using the formula 2-A instead of 2-bromo-9,10- dinaphthylanthracene Synthesis to prepare the compound of formula 4-A.

MS: [M + H] ⁺ = 499

Preparation Example 24 Synthesis of Compound of Formula 4-B

Method of synthesizing the compound of Formula 1-A, except that Formula 2-B was used instead of 2-bromo-9,10-dinaphthylanthracene in the synthesis of Compound 1-A of Preparation Example 1 Synthesis was performed in the same manner as to prepare a compound of Formula 4-B.

MS: [M + H] ⁺ = 499

Example 15 Synthesis of Compound of Formula 4-12

Except for using the formula 4-A instead of the formula 3-D in the synthesis of the compound of Formula 3-12, synthesized in the same manner as the synthesis method of the compound of Formula 3-12 The compound was prepared.

MS: [M + H] ⁺ = 1172

Example 16 Synthesis of Compound of Formula 4-22

[Formula 4-22]

Except for using the formula 4-B instead of the formula 3-D in the synthesis of the compound of Formula 3-12, and synthesized in the same manner as the synthesis method of the compound of Formula 3-12 The compound was prepared.

MS: [M + H] ⁺ = 1172

Example 17 Synthesis of Compounds of Formulas 11-A, 11-B, and 2-2

[Formula 11-A]

Benzyl (5 g, 23.8 mmol), ammonium acetate (2.75 g, 35.7 mmol), benzaldehyde (3.71 g, 23.7 mmol), 2-amino anthraquinone (26.53 g, 119 mmol) was acetic acid (40 mL) Suspended in. 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 obtain the compound of formula 11-A (5.9 g, 50%).

MS: [M + H] ⁺ = 503

[Formula 11-B]

Dissolve 2-bromonaphthalene (34.8 g, 168.2 mmol) in tetrahydrofuran (250 ml), lower the temperature to -78 ° C, slowly add n-butyllithium (67.3 ml, 168.2 mmol) and stir for 1 hour. It was. Formula 11-A (36.7 g, 73.1 mmol) was added thereto, 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 11-B (45.5 g, 82%).

MS: [M + H] ⁺ = 759

 [Formula 2-2]

The compound of Formula 11-B (45.1 g, 59.5 mmol), potassium iodide (29.6 g, 178.4 mmol), sodium hypophosphite (38 g, 256.8 mmol) was 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 2-2 (34.5 g, 80%).

MS: [M + H] < ⁺ > = 725

<Experimental Example 1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by 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.

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.

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

The compound of Formula 1-12 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.

Lithium fluoride (LiF) and aluminum having a thickness of 2000 Å were sequentially deposited on the electron injection and transport layer to a thickness of 12 Å to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr.

As a result of applying a forward electric field of 4.2 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 2>

An organic EL device was manufactured in the same manner as in Experiment 1, except that the compound of Formula 1-22 was used instead of the compound of Formula 1-12.

As a result of applying a forward electric field of 3.9 V to the organic light emitting device, green light was observed at 21 mA / cm2 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 a compound of Formula 2-12 was used instead of a compound of Formula 1-12.

As a result of applying a forward electric field of 3.4 V to the organic light emitting device prepared above, green light was observed at 27 cd / A 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 the compound of Formula 2-22 was used instead of the compound of Formula 1-12.

As a result of applying a forward electric field of 3.3 V to the organic light emitting device, 25 cd / A was observed 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 a compound of Formula 4-12 was used instead of a compound of Formula 1-12.

As a result of applying a forward electric field of 3.5 V to the organic light emitting device prepared above, green light was observed at 23 cd / A 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 2-2 was used instead of a compound of Formula 1-12.

As a result of applying a forward electric field of 3.4 V to the organic light emitting device prepared above, green light was observed at 26 cd / A at a current density of 5 mA / cm 2.

&Lt; 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 an 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.

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.

DESCRIPTION OF THE REFERENCE NUMERALS

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 of Formulas 2-12 of the present invention.

Claims (30)

Imidazole derivatives represented by the following formula (1): [Formula 1]

In 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 and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or unsubstituted 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 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 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, At least one of R3 to R10 is a group represented by the following formula (2) or formula (3), (2)

(3)

In Chemical Formulas 2 and 3, R11 to R16 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 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl substituted by at least one group selected from the group consisting of Al, or the unsubstituted C ₁ ~ C ₄₀ kilgi; 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 group heteroaryl is substituted by at least one group selected from the group true luer 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 L ₁ and L ₂ 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 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 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 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 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 C ₂₅ to C ₄₀ open spiro group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl groups, C ₆ to C ₄₀ aryl groups and C ₅ to C ₄₀ heteroaryl groups; , R3 to R10 other than the group represented by the formula (2) or (3) is 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 imidazole derivative according to claim 1, wherein R 1 and R 2 in Formula 1 are the same aryl group. The imidazole derivative of claim 1, wherein R 1 and R 2 in Formula 1 are the same heteroaryl group. The imidazole derivative according to claim 1, wherein R1 and R2 of Formula 1 are amino groups substituted with the same aryl group or heteroaryl group. The imidazole derivative of 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 aryl substituted with a H. interrogating by at least one group 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 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 be. The method according to claim 1, Two or more selected from R11, R12 and R13 of the formula (2); And at least two selected from R 14, R 15, and R 16 in Formula 3 are the same aryl group. The method according to claim 1, Two or more selected from R11, R12 and R13 of the formula (2); And at least two selected from R 14, R 15 and R 16 in Formula 3 are the same heteroaryl group. The method according to claim 1, Two or more selected from R11, R12 and R13 of the formula (2); And at least two selected from R14, R15, and R16 of Formula 3 are amino groups substituted with the same aryl group or heteroaryl group. The method according to claim 1, At least one of R11, R12 and R13 of the formula (2); And at least one of R14, R15, and R16 of Formula 3 is hydrogen. The imidazole derivative of claim 1, wherein L ₁ and L ₂ of Formula ₂ are a direct bond or selected from the group consisting of:

The imidazole derivative according to claim 1, wherein the imidazole derivative is selected from compounds represented by the following Chemical Formulas 4 to 7: [Formula 4]

[Chemical Formula 5]

[Formula 6]

[Formula 7]

In Formulas 4 to 7, wherein R1 to R16, L ₁ and L ₂ are as defined in claim 1. The imidazole derivative according to claim 11, wherein the compound represented by Chemical Formula 4 includes a compound represented by the following Chemical Formula wherein R3 to R10 are hydrogen:

The imidazole derivative according to claim 11, wherein the compound represented by Chemical Formula 5 includes a compound represented by the following Chemical Formula wherein R3 to R10 are hydrogen:

The imidazole derivative according to claim 11, wherein the compound represented by Chemical Formula 6 includes a compound represented by the following Chemical Formula wherein R3 to R10 are hydrogen:

The imidazole derivative according to claim 11, wherein the compound represented by Formula 7 includes a compound represented by the following formula wherein R3 to R10 are hydrogen:

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 includes an imidazole derivative. As an element, The imidazole derivative is an organic electronic device which is an imidazole derivative represented by Formula 1 below: [Formula 1]

In 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 and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or unsubstituted 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 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 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, At least one of R3 to R10 is a group represented by the following formula (2) or formula (3), (2)

(3)

In Chemical Formulas 2 and 3, R11 to R16 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 L ₁ is C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ of the alkynyl group, an alkoxy group of _{C 1 -C 40, C 6 ~} C 40 aryl group and a C ₅ ~ of C ₂ ~ C ₄₀ alkenylene group unsubstituted or substituted with one or more groups selected from the group consisting of 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 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 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 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 C ₂₅ to C ₄₀ open spiro group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl groups, C ₆ to C ₄₀ aryl groups and C ₅ to C ₄₀ heteroaryl groups; , 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 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 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 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 C ₂₅ to C ₄₀ open spiro group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl groups, C ₆ to C ₄₀ aryl groups and C ₅ to C ₄₀ heteroaryl groups; , R3 to R10 other than the group represented by the formula (2) or (3) is 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 organic electronic device of claim 16, 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 16, wherein the organic electronic device is an organic light emitting device. The organic electronic device of claim 18, wherein the organic light emitting device is an organic light emitting device having a forward structure in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate. The organic electronic device of claim 18, 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 18, wherein the organic material layer of the organic light emitting device includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer and a light emitting layer. . The organic electronic device of claim 18, wherein the organic material layer of the organic light emitting device includes a light emitting layer, and the light emitting layer includes the imidazole derivative. The organic electronic device of claim 18, wherein the organic material layer of the organic light emitting device includes one or more layers selected from the group consisting of an electron transport layer, an electron injection layer, and an electron transport and injection layer. The organic electronic device of claim 18, 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 18, wherein the organic material layer of the organic light emitting device includes a layer for simultaneously emitting light and transporting electrons. The organic electronic device of claim 16, wherein the imidazole derivative is an imidazole derivative selected from compounds represented by the following Chemical Formulas 4 to 7: [Formula 4]

[Chemical Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 4 to 7, wherein R1 to R16, L ₁ and L ₂ are as defined in claim 16. 27. The organic electronic device of claim 26, wherein the compound represented by Chemical Formula 4 comprises an imidazole derivative comprising a compound represented by the following formula wherein R3 to R10 are hydrogen:

The organic electronic device according to claim 26, wherein the compound represented by Chemical Formula 5 includes an imidazole derivative comprising a compound represented by the following Chemical Formula wherein R3 to R10 are hydrogen:

27. The organic electronic device of claim 26, wherein the compound represented by Chemical Formula 6 includes an imidazole derivative, wherein the compound represented by the following Chemical Formula wherein R3 to R10 is hydrogen:

27. The organic electronic device of claim 26, wherein the compound represented by Chemical Formula 7 includes an imidazole derivative comprising a compound represented by the following formula wherein R3 to R10 are hydrogen:

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