KR20140009095A - New imidazole derivatives and organic electronic device using the same - Google Patents

Abstract

The present invention provides a new imidazole derivative and an organic electronic device using the same. The organic electronic device of the present invention has excellent efficiency, driving voltage, and lifetime. The organic electronic device includes a first electrode, a second electrode, and more than one layer of organic matter layers located in between the first and second electrodes.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel imidazole derivative, and an organic electronic device using the same. BACKGROUND OF THE INVENTION < RTI ID =

The present invention relates 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 the exchange of holes and / or electrons between the electrode and the 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. These devices include an electron / hole injecting material, an electron / hole extracting material, Materials or luminescent materials. 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.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on 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. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host 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, organometallic complexes having a relatively high stability to electrons and an electron transfer rate as organic monomolecular materials are preferable as electron transporting materials. 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. Flavon derivatives of sanyo or germanium and silicon clopetadiene derivatives of Chisso are known (Japanese Patent Laid-Open Publication No. 1998-017860, Japanese Laid-Open Patent Publication 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 arbitrary luminescent color by changing the structure of an organic monomolecular material used in an organic luminescent device or obtaining various high efficiencies by a host dopant system have been proposed, Characteristics, life span and durability.

For example, Korean Patent Publication No. 2003-0067773 discloses a compound having a benzoimidazole ring and an anthracene skeleton.

Further, there are cases where the organic EL device has a further improved light emission luminance, efficiency, and lifetime through the additional charge generation capability in addition to the charge to be injected. Examples thereof include inorganic salts and the like in a transport layer Or an injection layer), or an organic material or a complex thereof is used together. (2002) pp. L800-L803, "Organic electroluminescent devices having metal complexes as cathode interface layer ", Junji, Kido et al., Jpn. J. Appl. Phys.

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.

The present inventors have found imidazole derivatives having a novel structure. In addition, when the organic imide layer of the organic electronic device is formed using the new imidazole derivative, it has been found that the efficiency of the device can be increased, the driving voltage can be lowered, the lifetime can be increased, and the stability can be increased.

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

The present invention provides novel imidazole derivatives.

The present invention provides 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 comprises the novel imidazole derivative Wherein the organic electronic device is an organic electronic device.

The novel imidazole derivatives according to the present invention can be used as organic material layers of organic electronic devices including organic light emitting devices. The novel imidazole derivatives according to the present invention exhibit excellent properties in terms of efficiency, driving voltage and lifetime, as well as organic electronic devices including organic light emitting devices used as materials for organic materials.

1 illustrates an example of an organic light emitting device according to the present invention.
2 is an MS graph of a compound of Formula 2-67 of the present invention.

Imidazole derivatives according to the present invention include compounds represented by the following formula (1):

In Formula 1,

At least one of R 1 to R 10 is a compound represented by the following general formula (2), and the others are the same or different and each independently represents hydrogen; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, Substituted or unsubstituted with at least one group selected from the group consisting of a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, -SiR ₃ , -GeR ₃ , -SnR ₃ and C ₅ to C ₄₀ heteroaryl groups, A substituted C ₆ to C ₄₀ aryl group; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, Substituted or unsubstituted with at least one group selected from the group consisting of a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, -SiR ₃ , -GeR ₃ , -SnR ₃ and C ₅ to C ₄₀ heteroaryl groups, A substituted C ₅ -C ₄₀ heteroaryl group; And a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₁ to C ₄₀ alkoxy group, a C ₃ to C ₄₀ cycloalkyl group , A C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, -SiR ₃ , -GeR ₃ , -SnR ₃ and a C ₅ to C ₄₀ heteroaryl group, Unsubstituted amino groups, wherein R may be the same or different and are each independently C ₆ to C ₄₀ aryl or C ₅ to C ₄₀ heteroaryl,

In Formula 2,

L ₁ is a direct bond; An alkoxy group of C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, C ₁ -C ₄₀ of, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group with one or more groups selected from the group consisting of A C ₂ to C ₄₀ alkenylene group substituted or unsubstituted by a group; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C over one selected from the heteroaryl group consisting of ₄₀ group a substituted or unsubstituted C ₆ ~ C _40; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ by at least one group selected from the heteroaryl group consisting of a substituted or unsubstituted C ₅ ~ C ₄₀ of; Heterocycloalkyl group of 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 of, C ₆ ~ C ₄₀ the aryl group and the arylamine group of C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₆ ~ C ₄₀ of; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ A C ₂₅ to C ₄₀ spiro group substituted or unsubstituted with at least one group 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; And a halogen, an amino group, a nitrile group, a 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 open is selected from the group consisting of a spiro of the heteroaryl group substituted or unsubstituted with one or more groups selected from the group consisting of C ₂₅ ~ C ₄₀ of ,

Ar ₁ is hydrogen; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, C ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group, and a C ₅ ~ C ₄₀ heteroaryl substituted with an aryl group by at least one group selected from the group consisting of or unsubstituted alkyl group of C ₁ ~ C ₄₀ of; Deuterium, 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 substituted with an aryl group by at least one group selected from the group consisting of or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group of; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, C ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl substituted with an aryl group by at least one group selected from the group consisting of or unsubstituted C ₂ ~ C ₄₀ alkenyl group a; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, A C ₃ to C ₄₀ alkoxy group substituted or unsubstituted with at least one group selected from the group consisting of a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, An amino group substituted or unsubstituted with at least one group selected from the group consisting of a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, From the group consisting of C ₂ to C ₄₀ heterocycloalkyl groups, C ₆ to C ₄₀ aryl groups, C ₅ to C ₄₀ heteroaryl groups, C ₂₅ to C ₄₀ spiro groups and C ₂₅ to C ₄₀ open spiro groups. A C ₆ to C ₄₀ aryl group substituted or unsubstituted with at least one group selected; And a halogen, an amino group, a nitrile group, a 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, C ₅ ~ C ₄₀ heteroaryl group, C ₂₅ ~ C ₄₀ of a spiro group and a C ₂₅ ~ C ₄₀ open spiro group with one or more groups selected from the group consisting of A substituted or unsubstituted C ₅ -C ₄₀ heteroaryl group; -SiR _3; -GeR ₃ ; And -SnR ₃ , wherein R may be the same or different and are each independently C ₆ -C ₄₀ aryl or C ₅ -C ₄₀ heteroaryl.

The compounds represented by Formula 1 include compounds represented by the following Formulas 3 to 5:

In the above formulas (3) to (5)

R1 to R10, L ₁ and Ar ₁ are as defined in formula (I).

In the imidazole derivative according to the present invention, it is preferable that at least one of R 1 to R 10 in the above formula (1) is a compound represented by the above formula (2), and at least one of them is a C ₆ to C ₄₀ aryl group.

In the imidazole derivative according to the present invention, at least one of R 1 to R 10 in the formula (1) is a compound represented by the above formula (2), and at least one of them is a C ₅ to C ₄₀ heteroaryl group.

In the imidazole derivative according to the present invention, at least one of R1 to R10 of Chemical Formula 1 is a compound represented by Chemical Formula 2, and at least one of the others is selected from an amino group substituted with an aryl group or a heteroaryl group.

In the imidazole derivative according to the present invention, it is preferable that at least one of R 1 to R 10 in Formula 1 is the compound represented by Formula 2, and at least one of the others is hydrogen.

In the imidazole derivative according to the present invention, it is preferable that at least one of R 1 to R 10 in Formula 1 is a compound represented by Formula 2, and at least one of R 1 to R 10 is a C ₁ to C ₄₀ alkyl group.

In the imidazole derivative represented by Formula 1 according to the present invention, at least one of R 1 to R 10 is a compound represented by Formula 2, and at least one of R 1 to R 10 is preferably selected from the group consisting of:

Z1 to Z3 in the structural formula are the same or different from each other, and each independently hydrogen; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, an aryl group of 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 C ₆ ~ C ₄₀ of the; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ by at least one group selected from the heteroaryl group consisting of a substituted or unsubstituted C ₅ ~ C ₄₀ of; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ An amino group substituted or unsubstituted with at least one group 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; -SiR _3; -GeR ₃ ; And -SnR ₃ , wherein R may be the same or different and are each independently C ₆ -C ₄₀ aryl or C ₅ -C ₄₀ heteroaryl.

In the imidazole derivative according to the present invention, when Ar _{1 in} Formula 2 is an aryl group, it is preferably selected from the group consisting of the following structural formulas:

In the above formulas, Z4 is each independently hydrogen; Deuterium; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a 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 a C ₆ ~ C _40; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ by at least one group selected from the heteroaryl group consisting of a substituted or unsubstituted C ₅ ~ C ₄₀ of; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ An amino group substituted or unsubstituted with at least one group 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; A spiro group of C ₂₅ to C ₄₀ ; An open spiro group of C ₂₅ to C ₄₀ ; -SiR _3; -GeR ₃ ; And -SnR ₃ , wherein R may be the same or different and are each independently C ₆ -C ₄₀ aryl or C ₅ -C ₄₀ heteroaryl.

In addition, L < ₁ > in the above formula (2) is preferably selected from the group consisting of the following structural formulas:

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

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

The alkenyl group is preferably an alkenyl group having 2 to 40 carbon atoms.

The alkoxy group is preferably an alkoxy group having 1 to 40 carbon atoms.

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

Examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl- Amine, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole and a triphenylamine group, but is not limited thereto.

Examples of the heteroaryl group include a pyridyl group, bipyridyl group, triazine group, acridyl group, thiophene group, furan group, imidazole group, oxazole group, thiazole group, triazole group, quinoline group, But are not limited to these.

Examples of the halogen group include fluorine, chlorine, bromine or iodine.

Spiro groups are structures in which two ring organic compounds are connected to one atom,

등이 있다.

.

,

등이 있다. An open spiro group is a structure in which two ring compounds are disconnected in a structure in which two ring organic compounds are connected to one atom,

,

.

R 1 to R 4 in the above formula (1) are phenyl substituted with at least one member selected from naphthyl, phenyl, biphenyl and carbazolyl; Pyridyl substituted with phenanthryl or pyridyl; An amino group substituted with two phenyls; Pyranyl substituted with two phenyl; Isoquinolyl substituted with two phenyls; More preferably an alkyl group.

L ₁ is preferably a direct bond, phenylene, naphthylene, pyridylene, biphenylene or thienylene.

Ar ₁ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted pyrene group, a chrysene group, a tetracene group, a -SiR ₃ ; -GeR ₃ ; Or -SnR < ₃ >, wherein R is a phenyl group.

Preferable specific examples of the compound represented by the formula (3) include, but are not limited to, the following compounds.

Preferable specific examples of the compound represented by the formula (4) include, but are not limited to, the following compounds.

Specific examples of the compound represented by the formula (5) include, but are not limited to, the following compounds.

Hereinafter, a method for producing the compounds represented by the above Formulas 3 to 5 will be described.

Compounds represented by the formula (3) Ar ₁ to imidazole derivatives Lt; / RTI > may be prepared by introducing a substituent. Specifically, the compound represented by Chemical Formula 3 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 a phenanthrenequinone derivative. The resulting imidazole halide derivative and an Ar ₁ -boranic acid or an Ar ₁ -borone ester derivative can be produced by a Suzuki coupling reaction under a Pd catalyst.

Among the methods used in the preparation of the compound represented by the general formula (3), the reactions other than the Suzuki coupling reaction can be performed by a general method known in the art.

Specifically, the compound represented by the general formula (3)

1) preparing an imidazole ring through an acid catalyst by mixing an L ₁ derivative substituted with a halogen group and an aldehyde group, a phenanthrene quinone derivative having an R 3 to R 10 substituent, ammonium acetate, and an amine derivative having an R 2 substituent; And

2) preparing an imidazole derivative in which Ar ₁ is substituted by subjecting an imidazole derivative substituted with a halogen group and a boronic acid or boron ester compound having an Ar ₁ substituent group to Suzuki coupling reaction under a Pd catalyst .

Such a preparation method can be represented by the following reaction formula (1).

In the above Reaction Scheme 1, R 2 to R 10, L ₁ and Ar ₁ are as defined in Formula 3 above.

Hereinafter, the method for producing the compound represented by the above formula (4) will be described.

The compound represented by the above formula (4) Ar ₁ to imidazole derivatives Lt; / RTI > may be prepared by introducing a substituent. Specifically, the compound represented by Formula 4 may be prepared using an amine derivative substituted with a halide element, ammonium acetate, an aldehyde derivative, and a phenanthrene quinone derivative under an acid catalyst. The resulting imidazole halide derivative and an Ar ₁ -boranic acid or an Ar ₁ -borone ester derivative can be prepared by a Suzuki coupling reaction under a Pd catalyst.

Reactions other than the Suzuki binding reaction among the methods used when preparing the compound represented by Chemical Formula 4 may use a general method known in the art.

Specifically, the compound represented by the general formula (4)

1) Halide element and L ₁ Preparing an imidazole ring by an acid catalyst by mixing an amine derivative having a substituent, a phenanthrenequinone derivative having an R3 to R10 substituent, an ammonium acetate, and an aldehyde derivative having an R1 substituent, and

2) preparing an imidazole derivative in which Ar ₁ is substituted by subjecting an imidazole derivative substituted with a halogen group and a boronic acid or boron ester compound having an Ar ₁ substituent group to Suzuki coupling reaction under a Pd catalyst .

Such a preparation method can be represented by the following reaction formula (2).

In the above Reaction Scheme 2, R 1, R 2 to R 10, L _1, and Ar ₁ are as defined in Formula 4 above.

Hereinafter, the method for producing the compound represented by the above formula 5 will be described.

The compound represented by Formula 5 may be prepared by introducing an Ar ₁ substituent into an imidazole derivative. Specifically, the compound of Formula 5 may be prepared by using an acid catalyst such as a phenanthrene quinone derivative substituted with a halide element, an amine derivative, ammonium acetate, or an aldehyde derivative. The resulting imidazole halide derivative and an Ar ₁ -boranic acid or an Ar ₁ -borone ester derivative can be prepared by a Suzuki coupling reaction under a Pd catalyst.

The reactions other than the Suzuki coupling reaction among the methods used in the preparation of the compound of formula (5) can be performed by a general method known in the art.

Specifically, the compound represented by the general formula (5)

1) preparing an imidazole ring under acid catalyst by mixing a halide element and a phenanthrene quinone derivative having an L ₁ substituent, an amine derivative having an R 2 substituent, ammonium acetate, and an aldehyde derivative having an R 1 substituent, and

2) preparing an imidazole derivative in which Ar ₁ is substituted by Suzuki coupling reaction of a halogen-substituted imidazole derivative and a boronic acid or boron ester compound having an Ar ₁ substituent under a Pd catalyst; .

Such a preparation method can be represented by the following reaction formula (3).

In the above Reaction Scheme 3, R 1 to R 8, L ₁ and Ar ₁ are as defined in Formula 5 above.

The present invention also provides 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 represented by Formula 1 Wherein the organic compound is a compound represented by formula (I).

The organic electronic device of the present invention can be produced by a conventional method and materials for producing an organic electronic device, except that one or more organic material layers are formed using the above-described compounds.

Hereinafter, the organic light emitting device will be described.

In one embodiment of the present invention, the organic light emitting device may have a structure including a first electrode, a second electrode, and an organic layer disposed therebetween. The organic layer in the organic light emitting device of the present invention may have a single layer structure of one layer or a multilayer structure of two or more layers including a light emitting layer. When the organic material layer of the organic light emitting diode of the present invention has a multilayer structure, it may have a structure in which, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer 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. 1, reference numeral 1 denotes a substrate, 2 denotes an anode, 3 denotes a hole injecting layer, 4 denotes a hole transporting layer, 5 denotes an organic light emitting layer, 6 denotes an electron transporting layer and 7 denotes 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.

In the case where the organic light emitting device according to the present invention has an organic layer having a multilayer structure, the compound of the general formula (1) includes a light emitting layer, a hole transporting layer, a layer simultaneously transporting and emitting light, a layer simultaneously emitting light and electron transporting, And an injection layer, an electron injection layer, and the like. In the present invention, it is preferable that the compound of Chemical Formula 1 is included in at least one layer selected from the group consisting of electron injection and transport layer, electron transport layer, electron injection layer and luminescent layer.

In addition, when the organic light emitting device according to the present invention includes an organic material layer including at least one layer selected from the group consisting of an electron transport layer, an electron injection layer, and an electron injection and transport layer, the electron transport layer, electron injection layer, and electron injection. And at least one of the transport layers comprises the imidazole derivative, and the remaining layers preferably comprise a metal or metal compound.

When the organic light emitting device according to the present invention includes an organic material layer including at least one layer selected from the group consisting of an electron transporting layer, an electron injecting layer, and an electron injecting and transporting layer, the electron transporting layer, the electron injecting layer, And the transport layer preferably include the imidazole derivative, and the remaining layers include one selected from the group consisting of an alkali metal, an alkaline earth metal, an alkali metal compound, and an alkaline earth metal compound.

The organic electroluminescent device according to the present invention can be manufactured using conventional organic electroluminescent device manufacturing methods and materials, except that the compound of Formula 1 is used for at least one layer of the organic electroluminescent device. For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, A hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and the like, and then depositing a material usable as a cathode thereon . In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate in order to fabricate an organic light emitting device having a reverse structure as described above.

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 or a thermal transfer process, .

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

Hereinafter, preferred 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.

1. Method for producing the compound represented by the general formula (3)

< Manufacturing example  1> Synthesis of Compound of Formula 1-A

To a solution of 9-bromo-10- [naphthalene-2-yl] -anthracene (6.85 g, 17.9 mmol) in 150 ml of purified THF under nitrogen atmosphere, Was completely dissolved and then tert-butyllithium (31.5 mL, 1.7 M pentane solution) was added slowly at -78 ° C. After stirring at the same temperature for one hour, trimethyl borate (8 mL, 71.5 mmol) was added. The cooling vessel was removed and the reaction mixture was stirred at ambient temperature for 3 h. To the reaction mixture was added a 2 N aqueous hydrochloric acid solution (100 ml) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ethyl ether, and vacuum dried. Dried, dispersed in ethyl ether, stirred for 2 hours, filtered and dried to obtain the compound represented by the formula (1-A) (4.43 g, yield 71%) as white.

MS: [M + H] &lt; ⁺ &gt; = 349

< Manufacturing example  2> Synthesis of Compound of Formula 1-B

The synthesis of the compound of the formula 1-A of Preparation Example 1 was repeated except that 9-bromo-10- [naphthalene-2-yl] -anthracene was used instead of 9- The same procedure as in the synthesis of the compound of the above formula (I-A) was repeated except for using bromo-10- [naphthalen-1-yl] -anthracene (9-bromo-10- [naphthalene- To prepare the compound of the above formula (1-B).

MS: [M + H] &lt; ⁺ &gt; = 557

< Manufacturing example  3> 1-C, 1-D, 1- E of  Synthesis of compounds

[Chemical Formula 1-C]

Under N ₂ stream, 9-bromo-anthracene (8.2 g, 31.9 mmol), biphenyl boronic acid (7.6 g, 38.6 mmol), Pd (PPh 3) 4 (0.7 g, 0.6 mmol) K ₂ CO ₃ aqueous solution to 2M (300 mL) and THF (300 mL), and the mixture was refluxed and stirred for about 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture. The organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized from THF / EtOH to obtain the compound of the formula 1-C (8.5 g, 81%).

MS: [M] ^&lt; ⁺ & gt ^; = 330

[Chemical Formula 1-D]

The compound of the above formula (1-C) (8.0 g, 24.2 mmol) was dissolved in chloroform (150 mL) under N ₂ flow and acetic acid (150 mL) was added. Br ₂ (1.3 mL, 25.4 mmol) Respectively. The mixture was warmed to room temperature and stirred for 5 hours. After completion of the reaction, the reaction solution was concentrated and recrystallized with EtOH to obtain the compound of the above formula (1-D) (7 g, 71%).

MS: [M] ^&lt; ⁺ & gt ^; = 408

[Chemical Formula 1-E]

Ether (80 mL) dehydrated and dehydrated toluene (80 mL) were added to the compound of the above formula (1-D) (7 g, 17.1 mmol) under N ₂ stream and cooled to -64 ° C in an ice bath. A 2.5 M butyllithium / hexane solution (9 mL) was added dropwise thereto over 30 minutes, and the mixture was reacted at -64 캜 for 2 hours. To this was added boric acid triisoste (12 mL) dropwise over 15 minutes. After the addition, the mixture was stirred at room temperature for 12 hours. The mixture was ice-cooled and 2N hydrochloric acid (70 mL) was added at 10 DEG C or lower, and toluene (30 mL) was added thereto. This was separated, dried over magnesium sulfate, concentrated under reduced pressure and recrystallized from hexane to obtain a yellow solid. To the solid was added concentrated hydrochloric acid (7 mL) and tetrabutylammonium bromide (0.04 g, 0.1 mmol), dissolved in THF (100 mL), and reacted at room temperature for 12 hours. After completion of the reaction, H ₂ O was added to the reaction solution to solidify it, followed by filtration to obtain the compound of Formula 1-E (3.2 g, 50%).

MS: [M] ^&lt; ⁺ & gt ^; = 374

< Manufacturing example  4> Synthesis of Compound of Formula 1-F

2-Naphthaleneboronic acid (10 g, 48.3 mmol) and 2-bromo-6-naphthol (10.8 g, 48.3 mmol) were completely dissolved in tetrahydrofuran (100 mL), and a 2M aqueous potassium carbonate solution Tetraquistriphenylphosphinopalladium (1.11 g, 2 mol%) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the water layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then subjected to column chromatography with tetrahydrofuran: hexane = 1: 6 to prepare the compound of Formula 1-F (8.5 g, 65%).

MS: [M + H] &lt; ⁺ &gt; = 271

< Manufacturing example  5> Synthesis of Compound of Formula 1-G

The compound of Formula 1-F (7.2 g, 26.8 mmol) was dissolved in dichloromethane, triethylamine (7.47 mL, 53.6 mmol) was added, and the mixture was stirred for 10 minutes. After the temperature was lowered to 0 ° C, trifluoromethanesulfonic anhydride (4.4 mL, 40.2 mmol) was slowly added thereto, the temperature was raised to room temperature, and the mixture was stirred for 1 hour. The aqueous sodium bicarbonate solution was added, the water layer was removed, and water was removed with anhydrous magnesium sulfate. Filtered, concentrated under reduced pressure, and recrystallized with hexane to obtain the compound of the formula 1-G (8.74 g, 81%).

MS: [M + H] &lt; ⁺ &gt; = 403

< Manufacturing example  6> Synthesis of Compound of Formula 1-H

(3.95 g, 9.82 mmol), bis (pinacolato) diboron (2.75 g, 10.9 mmol) and potassium acetate (2.89 g, 29.4 mmol) were suspended in dioxane (50 mL) . Palladium (diphenylphosphinoferrocene) chloride (0.24 g, 3 mol%) was added to the suspension. The resulting mixture was stirred at 80 &lt; 0 &gt; 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-H (3.36 g, 90%).

MS: [M + H] &lt; ⁺ &gt; = 381

< Manufacturing example  7> Synthesis of Compound of Formula 1-I

A mixture of 9,10-Phenanthrenequinone (2.08 g, 10 mmol), ammonium acetate (1.16 g, 15 mmol), aniline (4.67 g, 50 mmol), 4-bromo-benzaldehyde g, 10 mmol) was suspended in acetic acid (20 mL). The resulting mixture was stirred at 100 &lt; 0 &gt; C for about 6 hours and cooled to room temperature. The mixture was diluted with water (50 mL), and the resulting solid was filtered, washed with water and ethyl ether to obtain the compound of the formula (I-I) (2.7 g, 62%).

MS: [M + H] &lt; ⁺ &gt; = 450

< Manufacturing example  8> Synthesis of Compound of Formula 1-J

The compound of the formula (I-J) was prepared in the same manner as the compound of the formula (I-I) except that 3-bromo-benzaldehyde was used instead of 4-bromo-benzaldehyde.

MS: [M + H] &lt; ⁺ &gt; = 450

< Manufacturing example  Synthesis of Compound of Formula 1-K

The compound of the formula 1-K was prepared in the same manner as the compound of the formula 1-I except that 1-amino-naphthalene was used instead of aniline.

MS: [M + H] &lt; ⁺ &gt; = 500

< Manufacturing example  10> Synthesis of Compound of Formula 1-L

(1.16 g, 15 mmol), aniline (4.67 g, 50 mmol), 6-bromo-2-naphthalenaldehyde (2.56 g, 10 mmol) was suspended in acetic acid (20 mL). The resulting mixture was stirred at 100 &lt; 0 &gt; 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 to obtain the compound of formula 1-L (3.0 g, 60%).

MS: [M + H] &lt; ⁺ &gt; = 500

< Manufacturing example  11> Synthesis of Compound of Formula 1-M

Except that 1-bromo-phenylene was used in place of 9-bromo-10- [naphthalen-2-yl] -anthracene instead of 9- Compound (1-M) was prepared in the same manner as Compound (A-1).

MS: [M] ^&lt; ⁺ & gt ^; = 246

< Manufacturing example  12 Synthesis of Compound of Formula 11-A

2-bromo-9,10-dinaphthylanthracene (5.00 g, 9.82 mmol), bis (pinacolato) diboron (2.75 g, 10.9 mmol) and potassium acetate (2.89 g, 29.4 mmol) were added to dioxane ( 50 mL). Palladium (diphenylphosphinoferrocene) chloride (0.24 g, 3 mol%) was added to the suspension. The resulting mixture was stirred at 80 &lt; 0 &gt; 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 11-A (5.46 g, 92%) as 9,10-dinaphthylanthracenyl-2-borate.

MS: [M + H] &lt; ⁺ &gt; = 557

< Manufacturing example  Synthesis of the compound of the following formula 11-B

1-Bromonaphthalene (34.8 g, 168.2 mmol) was dissolved in tetrahydrofuran (170 ml), the temperature was lowered to -78 ° C, n-butyllithium (67.3 ml, 168.2 mmol) Lt; / RTI &gt; 2-Bromoanthraquinone (21 g, 73.1 mmol) was added, the temperature was raised to room temperature and stirred for 3 hours. Saturated aqueous ammonium chloride solution was added to remove water layer, dried with anhydrous magnesium sulfate, filtered and dried under reduced pressure. Recrystallization with ethyl ether and petroleum ether to prepare the compound of formula 11-B (32.3 g, 82%).

MS: [M + H] &lt; ⁺ &gt; = 544

< Manufacturing example  14> Synthesis of Compound of Formula 11-C

Sodium hypophosphite (38 g, 256.8 mmol) was added to the above compound (32.3 g, 59.5 mmol), potassium iodide (29.6 g, 178.4 mmol) and acetic acid (40 mL) The precipitate was filtered and then recrystallized from ethanol to obtain the compound of the formula 11-C (25.5 g, 84%).

MS: [M + H] &lt; ⁺ &gt; = 509

< Manufacturing example  15> Synthesis of the compound of the following formula 11-D

Method for synthesizing the compound of Formula 11-A, except that Formula 11-C was used instead of 2-bromo-9,10-dinaphthylanthracene in the synthesis of Compound 11-A of Preparation Example 12 Synthesis was performed in the same manner as to prepare a compound of Formula 11-D.

MS: [M + H] &lt; ⁺ &gt; = 557

< Manufacturing example  16> Synthesis of the compound of the following formula 11-E

Iodobenzene (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 was refluxed under a nitrogen atmosphere. After cooling to room temperature, the product was extracted with ethyl acetate, the water was removed with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The product was passed through a silica gel column using a hexane solvent to obtain a compound. The solvent was removed under reduced pressure and vacuum drying was conducted to prepare the compound of the above formula (11-E) (1.6 g, 25%) as a white solid.

MS: [M + H] &lt; ⁺ &gt; = 322

< Manufacturing example  Synthesis of the compound of the following formula 11-F

The compound of formula 11-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-butyllithium (6.6 mL, 2.5 M hexane solution) was added slowly to the cooled solution over 10 minutes and then stirred at -78 ° C for about 40 minutes. The 2-bromoanthraquinone compound (3.59 g, 5.5 mmol) was added to the reaction mixture and further stirred at -78 [deg.] C for about 3 hours. The mixture was stirred at room temperature for about 1 hour. 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 in diethyl ether, stirred for 1 hour, and then filtered. After drying, the compound of formula 11-F (3.32 g, 73%) as a dialcohol compound was prepared.

MS [M + H] &lt; ⁺ &gt; = 773

< Manufacturing example  Synthesis of the compound of the following formula 11-G

The compound of Formula 11-F (2.82 g, 3.65 mmol) was added to a dispersion of acetic acid (60 mL), potassium iodate (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 then vacuum dried to give the compound of formula 11-G (2.87 g, 90%).

MS: [M + H] &lt; ⁺ &gt; = 739

< Manufacturing example  19> Synthesis of a compound of the following formula 11-H

The compound of Chemical Formula 11-A, except that the compound of Chemical Formula 11-G was used instead of 2-bromo-9,10-dinaphthylanthracene in the method for preparing the compound of Chemical Formula 11-A of Preparation Example 12 In the same manner as in the preparation of the compound of Formula 11-H was prepared.

MS [M + H] &lt; ⁺ &gt; = 787

< Manufacturing example  Synthesis of the compound of the following formula 11-I

4-Bromo-1-phenyl boronic acid (9.66 g 48.3 mmol) and bromobenzene _{-D 5 (7.77 g, 48.3 mmol} ) of 2M aqueous solution of potassium carbonate was completely dissolved in tetrahydrofuran (100 mL) (100 mL) And tetrakistriphenylphosphinopalladium (1.11 g, 2 mol%) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then subjected to column chromatography using hexane to prepare 8.1 g (70%) of the compound of formula 11-I.

MS: [M + H] &lt; ⁺ &gt; = 239

< Manufacturing example  Synthesis of a compound of the following formula 11-J

The compound of the above formula 11-A, except that the compound of the above formula 11-I was used instead of 2-bromo-9,10-dinaphthylanthracene in the preparation of the compound of the formula 11- The compound of the above formula 11-J was prepared in the same manner as the compound of the formula 11-J.

MS [M] ^&lt; ⁺ & gt ^; = 285

< Manufacturing example  Synthesis of a compound of the following formula 11-K

Dibromobenzene (23.5 g, 100 mmol) was dissolved in tetrahydrofuran (300 mL), the temperature was lowered to -78 ° C., 2.5 M n-butyllithium (40 ml, 100 mmol) Lt; / RTI &gt; Triphenylsilyl chloride (26.5 g, 90.0 mmol) was added and the temperature was raised to ambient temperature and stirred for 3 hours. Saturated aqueous ammonium chloride solution was added to remove water layer, dried with anhydrous magnesium sulfate, filtered and dried under reduced pressure. The residue was recrystallized from ethyl ether and petroleum ether to give the compound of formula 11-K (24.3 g, 65%).

MS: [M + H] &lt; ⁺ &gt; = 416

< Manufacturing example  Synthesis of Compound of Formula 11-L

The compound of the above formula 11-A, except that the compound of the formula 11-A was used instead of the compound of the formula 11-A in place of 2-bromo-9,10-dinaphthylanthracene in the above- The compound of the above formula 11-L was prepared in the same manner as in the preparation of the compound of the formula 11-L.

MS [M] ^&lt; ⁺ & gt ^; = 463

< Manufacturing example  Synthesis of the compound of the following formula 11-M

In the same manner as in the preparation of the compound of the formula 11-K, except for using the compound of the triphenylgermyl chloride instead of triphenylsilyl chloride in the preparation of the compound of the formula 11-K, To give the compound of the above formula (11-M).

MS [M] ^&lt; ⁺ & gt ^; = 460

< Manufacturing example  Synthesis of the compound of the following formula 11-N

In the same manner as in the preparation of the compound of the formula 11-L, except for using the compound of the formula 11-M instead of the compound of the formula 11-K in the process for the preparation of the compound of the formula 11-L of the preparation example 123, The compound of formula 11-N was prepared.

MS [M] ^&lt; ⁺ & gt ^; = 507

< Example  1> Synthesis of the compound of the following formula 1-5

The compound of Formula 1-A (2.79 g, 8.0 mmol) and the compound of Formula 1-I (2.83 g, 6.3 mmol) were completely dissolved in tetrahydrofuran (100 mL), and 2M aqueous potassium carbonate solution (20 mL) Tetrakistriphenylphosphinopalladium (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 subjected to column chromatography with tetrahydrofuran: hexane = 1: 6 to prepare the compound of Formula 1-5 (2.55 g, 60%).

MS: [M + H] &lt; ⁺ &gt; = 673

< Example  2> Synthesis of the compound of the following formula 1-6

The compound of Formula 1-6 was prepared in the same manner as the compound of Formula 1-5 except that the compound of Formula 1-I was used instead of the compound of Formula 1-I.

MS: [M + H] &lt; ⁺ &gt; = 723

< Example  3> Synthesis of the compound of the following formula 1-9

The compound of the above formula 1-9 was prepared in the same manner as in the preparation of the compound of the formula 1-5 except that the compound of the formula 1-J was used instead of the compound of the formula 1-I.

MS: [M + H] &lt; ⁺ &gt; = 673

< Example  4> Synthesis of the compound of the following formula 1-21

The compound of Formula 1-21 was prepared in the same manner as the compound of Formula 1-5 except that the compound of Formula 1-B was used instead of the compound of Formula 1-A.

MS: [M + H] &lt; ⁺ &gt; = 673

< Example  5> Synthesis of Compound of Formula 1-22

The compound of Formula 1-22 was prepared in the same manner as the compound of Formula 1-5 except that the compound of Formula 1-E was used instead of the compound of Formula 1-A.

MS: [M + H] &lt; ⁺ &gt; = 699

< Example  6> Synthesis of the compound of the following formula 1-33

The compound of Formula 1-33 was prepared in the same manner as the compound of Formula 1-5 except that the compound of Formula 1-A was used instead of the compound of Formula 1-A.

MS: [M + H] &lt; ⁺ &gt; = 623

< Example  7> Synthesis of the compound of the following formula 1-35

The compound of Formula 1-35 was prepared in the same manner as the compound of Formula 1-5 except that the compound of Formula 1-A was used instead of the compound of Formula 1-A.

MS: [M + H] &lt; ⁺ &gt; = 571

< Example  8> Synthesis of Compound of Formula 1-64

The compound of Formula 11-A (3.5 g, 8.0 mmol) and the compound of Formula I-I (2.83 g, 6.3 mmol) were completely dissolved in tetrahydrofuran (100 mL), and then 2 M aqueous potassium carbonate solution (20 mL) Tetrakistriphenylphosphinopalladium (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 1-64 (3.27 g, 65%).

MS: [M + H] &lt; ⁺ &gt; = 800

< Example  Synthesis of Compound of Formula 1-65

The compound of Formula 1-65 was prepared in the same manner as the compound of Formula 1-64 except for using the compound of Formula 11-D instead of the compound of Formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 800

< Example  10> Synthesis of the compound of the following formula 1-67

The compound of Formula 1-67 was prepared in the same manner as the compound of Formula 1-64 except for using the compound of Formula 11-H instead of the compound of Formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 1230

< Example  Synthesis of Compound of Formula 1-74

The compound of Chemical Formula 1-74 was prepared by the same method as the method of preparing Chemical Formula 1-64, except that Chemical Formula 1-J was used instead of Chemical Formula 1-I.

MS: [M + H] &lt; ⁺ &gt; = 800

< Example  12> Synthesis of the compound of the following formula 1-94

The compound of Formula 1-94 was prepared in the same manner as the compound of Formula 1-64 except for using the compound of Formula 1-L instead of the compound of Formula 1-I.

MS: [M + H] &lt; ⁺ &gt; = 850

< Example  13> Synthesis of Compound of Formula 1-128

The compound of the formula 1-128 was prepared in the same manner as the compound of the formula 1-64 except for using the compound of the formula 1-K instead of the compound of the formula 1-I.

MS: [M + H] &lt; ⁺ &gt; = 850

< Example  Synthesis of Compound of Formula 1-174

Compounds of the formula 1-174 were prepared in the same manner as the compound of the formula 1-64 except that the compound of the formula 11-J was used instead of the compound of the formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 528

< Example  Synthesis of a compound of the following formula 1-181

Compounds of the formula 1-181 were prepared in the same manner as the compound of the formula 1-64 except for using the compound of the formula 11-L instead of the compound of the formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 705

< Example  Synthesis of the compound of the following formula 1-182

The compound of Formula 1-182 was prepared in the same manner as the compound of Formula 1-64 except that the compound of Formula 11-N was used instead of the compound of Formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 750

2. Production method of the compound represented by the formula (4)

< Manufacturing example  20> Synthesis of Compound of Formula 2-A

(2.75 g, 35.7 mmol), benzaldehyde (3.71 g, 23.7 mmol), 4-bromo-aniline (20.47 g, g, 119 mmol) was suspended in acetic acid (40 mL). The resulting mixture was stirred at 100 &lt; 0 &gt; C for about 8 hours and cooled to room temperature. The mixture was diluted with water (100 mL), and the resulting solid was filtered, washed with water and ethyl, to obtain the compound of Formula 2-A (5.9 g, 55%).

MS: [M + H] &lt; ⁺ &gt; = 450

< Manufacturing example  21> Synthesis of Compound of Formula 2-B

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

MS: [M + H] &lt; ⁺ &gt; = 450

< Manufacturing example  22> Synthesis of the compound of the following formula 2-C

The compound of the formula 2-C was prepared in the same manner as the compound of the formula 2-A except that 6-bromo-2-aminonaphthalene was used instead of 4-bromo-aniline.

MS: [M + H] &lt; ⁺ &gt; = 500

< Manufacturing example  23> Synthesis of the compound of the following formula 2-D

The compound of the above formula 2-D was prepared in the same manner as the compound of the above formula 2-A except for using 2-naphthalene aldehyde instead of benzaldehyde.

MS: [M + H] &lt; ⁺ &gt; = 500

< Manufacturing example  24> Synthesis of the compound of the following formula 2-E

The compound of the above formula 2-E was prepared in the same manner as the compound of the above formula 2-A except for using 2-pyridine aldehyde instead of benzaldehyde.

MS: [M + H] &lt; ⁺ &gt; = 451

< Example  14> Synthesis of Compound of Formula 2-1 below

The compound of Formula 1-A (2.79 g, 8.0 mmol) and the compound of Formula 2-A (2.83 g, 6.3 mmol) were completely dissolved in tetrahydrofuran (100 mL), followed by 2 M aqueous potassium carbonate solution (20 mL). Tetrakistriphenylphosphinopalladium (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 2-1 (2.75 g, 65%).

MS: [M + H] &lt; ⁺ &gt; = 673

< Example  15> Synthesis of Compound of Formula 2-5

The compound of Formula 2-5 was prepared in the same manner as the compound of Formula 2-1 except that the compound of Formula 2-B was used instead of the compound of Formula 2-A.

MS: [M + H] &lt; ⁺ &gt; = 673

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

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

MS: [M + H] &lt; ⁺ &gt; = 723

< Example  17> Synthesis of Compound of Formula 2-3

The compound of Formula 2-3 was prepared in the same manner as the compound of Formula 2-1 except that the compound of Formula 2-E was used instead of the compound of Formula 2-A.

MS: [M + H] &lt; ⁺ &gt; = 674

< Example  18> Synthesis of the compound of the following formula 2-9

The compound of Chemical Formula 2-9 was prepared by the same method as the method of preparing Chemical Formula 2-1, except that Chemical Formula 2-C was used instead of Chemical Formula 2-A.

MS: [M + H] &lt; ⁺ &gt; = 723

< Example  19> Synthesis of Compound of Formula 2-17

The compound of Formula 2-17 was prepared in the same manner as the compound of Formula 2-1 except that the compound of Formula 1-B was used instead of the compound of Formula 1-A.

MS: [M + H] &lt; ⁺ &gt; = 673

< Example  20> Synthesis of Compound of Formula 2-18

The compound of Formula 2-18 was prepared in the same manner as the compound of Formula 2-1 except that the compound of Formula 1-A was used instead of the compound of Formula 1-A.

MS: [M + H] &lt; ⁺ &gt; = 699

< Example  21> Synthesis of Compound of Formula 2-29

The compound of Formula 2-29 was prepared in the same manner as the compound of Formula 2-1 except that the compound of Formula 1-A was used instead of the compound of Formula 1-A.

MS: [M + H] &lt; ⁺ &gt; = 623

< Example  22> Synthesis of Compound of Formula 2-31

The compound of Formula 2-31 was prepared in the same manner as the compound of Formula 2-1 except that the compound of Formula 1-M was used instead of the compound of Formula 1-A.

MS: [M + H] &lt; ⁺ &gt; = 571

< Example  22-A, 22-B, 2- 57 of  Synthesis of compounds

[Chemical Formula 22-A]

(5 g, 23.8 mmol), ammonium acetate (2.75 g, 35.7 mmol), benzaldehyde (3.71 g, 23.7 mmol), 2-aminoanthraquinone (26.53 g , 119 mmol) was suspended in acetic acid (40 mL). The resulting mixture was stirred at 100 &lt; 0 &gt; C for about 8 hours and cooled to room temperature. The mixture was diluted with water (100 mL), and the resulting solid was filtered and washed with water and ethyl to obtain the compound of Formula 22-A (5.9 g, 50%).

MS: [M + H] &lt; ⁺ &gt; = 501

[Chemical Formula 22-B]

After dissolving 2-bromonaphthalene (34.8 g, 168.2 mmol) in tetrahydrofuran (250 ml), the temperature was lowered to -78 ° C and n-butyllithium (67.3 ml, 168.2 mmol) Lt; / RTI &gt; The above-mentioned compound 22-A (36.6 g, 73.1 mmol) was added, the temperature was raised to room temperature, and the mixture was stirred for 3 hours. Saturated aqueous ammonium chloride solution was added to remove water layer, dried with anhydrous magnesium sulfate, filtered and dried under reduced pressure. Recrystallization with ethyl ether and petroleum ether to prepare the compound of formula 22-B (44.3 g, 80%).

MS: [M + H] &lt; ⁺ &gt; = 757

 [Formula 2-57]

Sodium hypophosphite (38 g, 256.8 mmol) was added to the above compound (45.0 g, 59.5 mmol), potassium iodide (29.6 g, 178.4 mmol) and acetic acid (40 mL) . The precipitate was filtered and recrystallized from ethanol to obtain 34.4 g (80%) of the compound of Formula 2-57.

MS: [M + H] &lt; ⁺ &gt; = 723

< Example  24> 67 of  Synthesis of compounds

The compound of Formula 11-A (3.5 g, 8.0 mmol) and the compound of Formula 2-A (2.83 g, 6.3 mmol) were completely dissolved in tetrahydrofuran (100 mL), and then 2 M aqueous potassium carbonate solution (20 mL) Tetrakistriphenylphosphinopalladium (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 2-67 (3.27 g, 65%).

MS: [M] ^&lt; ⁺ & gt ^; = 799

< Example  Synthesis of the compound of the following formula 2-68

The compound of Formula 2-68 was prepared in the same manner as the compound of Formula 2-67 except for using the compound of Formula 11-D instead of the compound of Formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 800

< Example  26> Synthesis of the compound of the following formula 2-70

The compound of Formula 2-70 was prepared in the same manner as the compound of Formula 2-67 except for using the compound of Formula 11-H instead of the compound of Formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 1230

< Example  27> Synthesis of Compound of Formula 2-77

The compound of Formula 2-77 was prepared in the same manner as the compound of Formula 2-67 except for using the compound of Formula 2-B instead of the compound of Formula 2-A.

MS: [M + H] &lt; ⁺ &gt; = 800

< Example  28> Synthesis of Compound of Formula 2-97

The compound of Formula 2-97 was prepared in the same manner as the compound of Formula 2-67 except for using the compound of Formula 2-C instead of the compound of Formula 2-A.

MS: [M + H] &lt; ⁺ &gt; = 850

< Example  Synthesis of Compound of Formula 2-151

The compound of Formula 2-151 was prepared in the same manner as the compound of Formula 2-67 except for using the compound of Formula 2-D instead of the compound of Formula 2-A.

MS: [M + H] &lt; ⁺ &gt; = 850

< Example  Synthesis of Compound of Formula 2-131

The compound of Formula 2-131 was prepared in the same manner as the compound of Formula 2-67 except for using the compound of Formula 2-E instead of the compound of Formula 2-A.

MS: [M + H] &lt; ⁺ &gt; = 801

< Example  231> Synthesis of Compound of Formula 2-177

The compound of Formula 2-177 was prepared by the same method as the method of preparing Formula 2-67, except that Formula 11-J was used instead of Formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 528

< Example  232> Synthesis of Compound of Formula 2-184

The compound of Formula 2-184 was prepared in the same manner as the compound of Formula 2-67 except that the compound of Formula 11-L was used instead of the compound of Formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 705

< Example  233> Synthesis of Compound of Formula 2-185

A compound of Formula 2-185 was prepared by the same method as the method of preparing Formula 2-67, except that Formula 11-N was used instead of Formula 11-A.

MS: [M + H] &lt; ⁺ &gt; = 750

3. Method for producing the compound represented by the general formula (5)

< Manufacturing example  Synthesis of Compound of Formula 3-A

(3.66 g, 10 mmol), ammonium acetate (1.16 g, 15 mmol), aniline (4.67 g, 50 mmol), benzaldehyde (1.06 g, 10 mmol) Was suspended in acetic acid (20 mL). The resulting mixture was stirred at 100 &lt; 0 &gt; C for about 6 hours and cooled to room temperature. The mixture was diluted with water (50 mL), and the resulting solid was filtered and washed with water and ethyl to obtain the compound of Formula 3-A (3.17 g, 60%).

MS: [M + H] &lt; ⁺ &gt; = 529

< Manufacturing example  Synthesis of Compound of Formula 3-B

Except that 3,6-dibromo-9,10-phenanthrenequinone was used in place of 2,7-dibromo-9,10-phenanthrenequinone, -B. &Lt; / RTI &gt;

MS: [M + H] &lt; ⁺ &gt; = 529

< Example  31> Synthesis of Compound of Formula 3-26

The compound of Formula 1-A (4.83 g, 13.9 mmol) and the compound of Formula 3-A (3.33 g, 6.3 mmol) were completely dissolved in tetrahydrofuran (100 mL), followed by the addition of 2M potassium carbonate aqueous solution, Triphenylphosphinopalladium (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: 4 to prepare the compound of Chemical Formula 3-26 (3.07 g, 50%).

MS: [M + H] &lt; ⁺ &gt; = 976

< Example  32> Synthesis of Compound of Formula 3-34

The compound of Formula 3-34 was prepared in the same manner as the compound of Formula 3-26 except that the compound of Formula 3-B was used instead of the compound of Formula 3-A.

MS: [M + H] &lt; ⁺ &gt; = 976

< Example  33> Synthesis of Compound of Formula 3-53

After completely dissolving the compound of Formula 1-M (3.42 g, 13.9 mmol) and the compound of Formula 3-A (3.33 g, 6.3 mmol) in tetrahydrofuran (100 mL), an aqueous 2M potassium carbonate solution was added and tetrakis Triphenylphosphinopalladium (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 aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and subjected to column chromatography with tetrahydrofuran: hexane = 1: 4 to prepare the compound of Formula 3-53 (2.43 g, 50%).

MS: [M + H] &lt; ⁺ &gt; = 771

< Example  Synthesis of Compound of Formula 3-55

The compound of Formula 3-55 was prepared in the same manner as the compound of Formula 3-53 except that the compound of Formula 3-B was used instead of the compound of Formula 3-A.

MS: [M + H] &lt; ⁺ &gt; = 771

< 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. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as 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.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the ITO transparent electrode thus prepared to a thickness of 500 Å to form a hole injection layer.

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

Subsequently, GH and GD were vacuum deposited on the hole transport layer at a film thickness of 300 Å at a film thickness ratio of 20: 1 to form a light emitting layer.

The compound of Formula 1-5 prepared in Example 1 was vacuum deposited on the light emitting layer to a thickness of 200 Å 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 4.9 V to the organic light emitting device manufactured above, green light was observed at 19 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  2>

An organic EL device was fabricated in the same manner as in Experimental Example 1, except that the compound of Formula 1-64 was used in place of the compound of Formula 1-5.

As a result of applying a forward electric field of 4.7 V to the organic light emitting device manufactured above, green light was observed at 20 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  3>

An organic EL device was fabricated in the same manner as in Experimental Example 1 except that the compound of Formula 1-74 was used in place of the compound of Formula 1-5.

As a result of applying a forward electric field of 4.3 V to the organic light emitting device manufactured above, green light was observed at 20 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  4>

An organic EL device was fabricated in the same manner as in Experimental Example 1 except that the compound of Formula 2-31 was used in place of the compound of Formula 1-5.

As a result of applying a forward electric field of 4.3 V to the organic light emitting device manufactured above, green light was observed at 21 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  5>

An organic EL device was fabricated in the same manner as in Experimental Example 1 except that the compound of Formula 2-57 was used in place of the compound of Formula 1-5.

As a result of applying a forward electric field of 3.8 V to the organic light emitting device manufactured above, green light was observed at 22 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  6>

An organic EL device was fabricated in the same manner as in Experimental Example 1 except that the compound of Formula 2-67 was used in place of the compound of Formula 1-5.

As a result of applying a forward electric field of 3.8 V to the organic light emitting device, green light was observed at 21 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  7>

An organic EL device was prepared in the same manner as in Experimental Example 1 except that the compound of Formula 2-77 was used in place of the compound of Formula 1-5.

As a result of applying a forward electric field of 3.7 V to the organic light emitting device manufactured above, green light was observed at 22 cd / A at a current density of 5 mA / cm 2.

< Experimental Example  8>

An organic EL device was fabricated in the same manner as in Experimental Example 1 except that the compound of Formula 3-34 was used in place of the compound of Formula 1-5.

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

< Comparative Example  1>

(500 Å), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) on the ITO electrode prepared in the same manner as in Experimental Example 1, (200 ANGSTROM), lithium fluoride (LiF) 12 ANGSTROM, represented by the following chemical formula described in Korean Patent Laid-open Publication No. 2003-0067773, A hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer were sequentially formed by thermal vacuum deposition. 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, the green light was observed at 18 cd / A at a current density of 5 mA / cm 2.

1 substrate 2 anode
3 hole injection layer 4 hole transport layer
5 organic light emitting layer 6 electron transport layer
7 cathode

Claims (24)

Imidazole derivatives represented by the following formula (1):

In Formula 1,
At least one of R 1 to R 10 is a compound represented by the following general formula (2), and the others are the same or different and each independently represents hydrogen; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, Substituted or unsubstituted with at least one group selected from the group consisting of a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, -SiR ₃ , -GeR ₃ , -SnR ₃ and C ₅ to C ₄₀ heteroaryl groups, A substituted C ₆ to C ₄₀ aryl group; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, Substituted or unsubstituted with at least one group selected from the group consisting of a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, -SiR ₃ , -GeR ₃ , -SnR ₃ and C ₅ to C ₄₀ heteroaryl groups, A substituted C ₅ -C ₄₀ heteroaryl group; And a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₁ to C ₄₀ alkoxy group, a C ₃ to C ₄₀ cycloalkyl group , A C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, -SiR ₃ , -GeR ₃ , -SnR ₃ and a C ₅ to C ₄₀ heteroaryl group, Unsubstituted amino groups, wherein R may be the same or different and are each independently C ₆ to C ₄₀ aryl or C ₅ to C ₄₀ heteroaryl,

In Formula 2,
L ₁ is a direct bond; An alkoxy group of C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, C ₁ -C ₄₀ of, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group with one or more groups selected from the group consisting of A C ₂ to C ₄₀ alkenylene group substituted or unsubstituted by a group; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C over one selected from the heteroaryl group consisting of ₄₀ group a substituted or unsubstituted C ₆ ~ C _40; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ by at least one group selected from the heteroaryl group consisting of a substituted or unsubstituted C ₅ ~ C ₄₀ of; Heterocycloalkyl group of 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 of, C ₆ ~ C ₄₀ the aryl group and the arylamine group of C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₆ ~ C ₄₀ of; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ A C ₂₅ to C ₄₀ spiro group substituted or unsubstituted with at least one group 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; And a halogen, an amino group, a nitrile group, a 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 open is selected from the group consisting of a spiro of the heteroaryl group substituted or unsubstituted with one or more groups selected from the group consisting of C ₂₅ ~ C ₄₀ of ,
Ar ₁ is hydrogen; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, C ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group, and a C ₅ ~ C ₄₀ heteroaryl substituted with an aryl group by at least one group selected from the group consisting of or unsubstituted alkyl group of C ₁ ~ C ₄₀ of; Deuterium, 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 substituted with an aryl group by at least one group selected from the group consisting of or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group of; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, C ₂ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl substituted with an aryl group by at least one group selected from the group consisting of or unsubstituted C ₂ ~ C ₄₀ alkenyl group a; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, A C ₃ to C ₄₀ alkoxy group substituted or unsubstituted with at least one group selected from the group consisting of a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, An amino group substituted or unsubstituted with at least one group selected from the group consisting of a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, From the group consisting of C ₂ to C ₄₀ heterocycloalkyl groups, C ₆ to C ₄₀ aryl groups, C ₅ to C ₄₀ heteroaryl groups, C ₂₅ to C ₄₀ spiro groups and C ₂₅ to C ₄₀ open spiro groups. A C ₆ to C ₄₀ aryl group substituted or unsubstituted with at least one group selected; And a halogen, an amino group, a nitrile group, a 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, C ₅ ~ C ₄₀ heteroaryl group, C ₂₅ ~ C ₄₀ of a spiro group and a C ₂₅ ~ C ₄₀ open spiro group with one or more groups selected from the group consisting of A substituted or unsubstituted C ₅ -C ₄₀ heteroaryl group; -SiR _3; -GeR ₃ ; And -SnR ₃ , wherein R may be the same or different and are each independently C ₆ -C ₄₀ aryl or C ₅ -C ₄₀ heteroaryl. The imidazole derivative according to claim 1, wherein the imidazole derivative represented by Chemical Formula 1 is selected from the group consisting of imidazole derivatives represented by the following Chemical Formulas 3-5:

In the above formulas (3) to (5)
R1 to R10, L ₁ and Ar ₁ are as defined in formula (I). The imidazole derivative according to claim 1, wherein at least one of R1 to R10 of Chemical Formula 1 is a compound represented by Chemical Formula 2, and at least one of the remaining ones is an aryl group. The imidazole derivative according to claim 1, wherein at least one of R1 to R10 of Chemical Formula 1 is a compound represented by Chemical Formula 2, and at least one of the remaining ones is a heteroaryl group. The imidazole derivative according to claim 1, wherein at least one of R1 to R10 of Chemical Formula 1 is a compound represented by Chemical Formula 2, and at least one of others is a C ₁ to C ₄₀ alkyl group substituted with an aryl group or a heteroaryl group. . The imidazole derivative according to claim 1, wherein at least one of R 1 to R 10 in the formula (1) is a compound represented by the formula (2), and at least one of the others is hydrogen. The imidazole derivative according to claim 1, wherein at least one of R1 to R10 of Formula 1 is a compound represented by Formula 2, and at least one of the others is selected from the group consisting of the following structural formulas:

Z1 to Z3 in the structural formula are the same or different from each other, and each independently hydrogen; Heavy hydrogen (deuterium), a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ of the cycloalkyl group, an aryl group of 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 C ₆ ~ C ₄₀ of the; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ by at least one group selected from the heteroaryl group consisting of a substituted or unsubstituted C ₅ ~ C ₄₀ of; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ An amino group substituted or unsubstituted with at least one group 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; -SiR _3; -GeR ₃ ; And -SnR ₃ , wherein R may be the same or different and are each independently C ₆ -C ₄₀ aryl or C ₅ -C ₄₀ heteroaryl. The imidazole derivative according to claim 1, wherein Formula 2 is selected from the group consisting of the following structural formulas:

In the above formulas, Z4 is each independently hydrogen; Deuterium; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a 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 a C ₆ ~ C _40; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ by at least one group selected from the heteroaryl group consisting of a substituted or unsubstituted C ₅ ~ C ₄₀ of; A halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ cycloalkyl group of C ₄₀ of, C ₂ ~ C ₄₀ An amino group substituted or unsubstituted with at least one group 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; -SiR _3; -GeR ₃ ; And -SnR ₃ , wherein R may be the same or different and are each independently C ₆ -C ₄₀ aryl or C ₅ -C ₄₀ heteroaryl. The imidazole derivative according to claim 1, wherein L ₁ in the formula (2) is selected from the group consisting of the following structural formulas:

The imidazole derivative according to claim 1, wherein the imidazole derivative represented by Chemical Formula 1 is selected from the group consisting of the following structural formulas:

The imidazole derivative according to claim 1, wherein the imidazole derivative represented by Chemical Formula 1 is selected from the group consisting of the following structural formulas:

The imidazole derivative according to claim 1, wherein the imidazole derivative represented by Chemical Formula 1 is selected from the group consisting of the following structural formulas:

1. An organic electronic device comprising a first electrode, a second electrode, and at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the imidazole derivative of claim 1 Organic electronic device. 14. The organic electronic device according to claim 13, 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. 14. The organic electronic device according to claim 13, wherein the organic electronic device is an organic light emitting device. 16. The organic electronic device according to claim 15, wherein the organic light emitting device is an organic light emitting device having a forward structure in which an anode, at least one organic material layer, and a cathode are sequentially stacked on a substrate. 16. The organic electronic device according to claim 15, wherein the organic light emitting device is an organic light emitting device having a reverse structure in which a cathode, one or more organic compound layers and an anode are sequentially stacked on a substrate. 16. The organic electronic device according to claim 15, wherein the organic material layer of the organic light emitting device comprises at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron injecting layer, an electron transporting layer and an electron injecting and transporting layer. 16. The organic electronic device according to claim 15, wherein the organic material layer of the organic light emitting device comprises a light emitting layer, and the light emitting layer comprises the imidazole derivative. 16. The organic electroluminescent device according to claim 15, wherein the organic material layer of the organic light emitting device comprises at least one layer selected from the group consisting of an electron transporting layer, an electron injecting layer, and an electron injecting and transporting layer, and the electron transporting layer, Wherein at least one layer selected from the group consisting of said imidazole derivatives is included. 16. The organic electronic device according to claim 15, wherein the organic material layer of the organic light emitting device comprises a layer simultaneously transporting and emitting light. 16. The organic electronic device according to claim 15, wherein the organic material layer of the organic light emitting device comprises a layer simultaneously emitting light and electron. The method according to claim 15, wherein the organic material layer of the organic light emitting device comprises at least one layer selected from the group consisting of an electron transport layer, an electron injection layer, and an electron injection and transport layer,
At least one of the electron transport layer, the electron injection layer, and the electron injection and transport layer includes the imidazole derivative, and the remaining layers include a metal or a metal compound. The method according to claim 15, wherein the organic material layer of the organic light emitting device comprises at least one layer selected from the group consisting of an electron transport layer, an electron injection layer, and an electron injection and transport layer,
At least one of the electron transport layer, the electron injection layer, and the electron injection and transport layer includes the imidazole derivative, and the remaining layers include one selected from the group consisting of alkali metals, alkaline earth metals, alkali metal compounds and alkaline earth metal compounds. The organic electronic device.

Images