KR20130100948A - New anthracene derivatives and organic electronic device using the same - Google Patents

Abstract

PURPOSE: An organic electronic device is provided to have excellent efficiency, driving voltage, and lifetime. CONSTITUTION: A compound of chemical formula 1 is provided. An organic electronic device contains a first electrode, a second electrode, and one or more organic layers placed between the first and second electrodes. The organic layers contain the compound. The organic electronic device is an organic light-emitting device. The organic electronic device is prepared by laminating an anode, one or more organic layers, and a cathode on a substrate.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel anthracene derivative and an organic electronic device using the same.

The present invention relates to a novel anthracene derivative having a triazine group bonded to anthracene and an organic electronic device using the same.

In the present specification, an organic electronic device is an electronic device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and an organic semiconductor material. The organic electronic device can be divided into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form. The second type is an electronic device 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 organic electronic devices include organic light emitting devices, organic solar cells, organic photoconductor (OPC) drums and organic transistors, all of which are electron / hole injection materials, electron / hole extraction materials, electron / hole transport materials for driving the devices. Materials or luminescent materials are required. Hereinafter, the organic light emitting device will be described in detail, 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. The organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer 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 organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like depending on their functions. The 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 fully exhibit the excellent characteristics of the above-described organic light emitting device, a material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material and an electron injection material, is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been sufficiently achieved, and therefore, the development of new materials is continuously required.

The inventors have discovered anthracene derivatives having a novel structure in which triazine groups are bound. In addition, it has been found that when the organic layer of the organic electronic device is formed using the novel anthracene derivative, effects such as an increase in efficiency of the device, a decrease in driving voltage, and an increase in stability may be exhibited.

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

The present invention provides a compound of Formula 1 below.

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, independently halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ alkoxy group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ of the heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or unsubstituted C ₆ ~ C ₄₀ aryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C _It is selected from the group consisting of C ₆ ~ C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group,

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

[Formula 2]

In Formula 2,

R5 and R6 are the same or different from each other and represent hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ amino group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of a group is selected from the group consisting of a heteroaryl unsubstituted C ₅ ~ C ₄₀ of Can and

L1 is a direct bond; A C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, a C ₂ -C ₄₀ alkynyl group of, C ₁ -C ₄₀ alkoxy group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ C ₂ -C ₄₀ alkenylene group unsubstituted or substituted with one or more groups selected from the group consisting of a heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C ₄₀ arylamine group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group substituted with one or more groups selected from the group consisting of groups or unsubstituted C ₅ ~ C ₄₀ heteroaryl group of; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₂₅ -C ₄₀ spiro group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ Is selected from the group consisting of C ₂₅ ~ C ₄₀ open spiro group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group, In the case of a substituted or unsubstituted C ₆ ~ C ₄₀ arylene group, except for the anthracene connected to the 9, 10 position, the two arylene groups may be connected.

A group other than the group represented by the formula (2) in R3 and R4 is hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C _It is selected from the group consisting of C ₆ ~ C ₄₀ arylamine group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group.

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

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

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 1-1 of the present invention.

The present invention provides a compound of Formula 1 below.

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, independently halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ alkoxy group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ of the heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or unsubstituted C ₆ ~ C ₄₀ aryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C _It is selected from the group consisting of C ₆ ~ C ₄₀ amino group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group,

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

[Formula 2]

In Formula 2,

R5 and R6 are the same or different from each other and represent hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ amino group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of a group is selected from the group consisting of a heteroaryl unsubstituted C ₅ ~ C ₄₀ of Can and

L1 is a direct bond; A C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, a C ₂ -C ₄₀ alkynyl group of, C ₁ -C ₄₀ alkoxy group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ C ₂ -C ₄₀ alkenylene group unsubstituted or substituted with one or more groups selected from the group consisting of a heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C ₄₀ arylamine group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group substituted with one or more groups selected from the group consisting of groups or unsubstituted C ₅ ~ C ₄₀ heteroaryl group of; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₂₅ -C ₄₀ spiro group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ Is selected from the group consisting of C ₂₅ ~ C ₄₀ open spiro group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group, In the case of a substituted or unsubstituted C ₆ ~ C ₄₀ arylene group, except for the anthracene connected to the 9, 10 position, the two arylene groups may be connected.

A group other than the group represented by the formula (2) in R3 and R4 is hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C _It is selected from the group consisting of C ₆ ~ C ₄₀ arylamine group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group.

In another exemplary embodiment of the present invention, R1 and R2 of Formula 1 may be the same aryl group. It is preferable that this aryl group is a substituted or unsubstituted phenyl group, a biphenyl group, or a naphthyl group.

In another exemplary embodiment of the present invention, R1 and R2 of Formula 1 may be the same heteroaryl group. It is preferable that this heteroaryl group is a substituted or unsubstituted pyridyl group, bipyridyl group, quinoline group, or isoquinoline group.

In another exemplary embodiment of the present invention, R1 and R2 of Formula 1 may be an amino group substituted with the same C ₆ ~ C ₄₀ aryl group or C ₅ ~ C ₄₀ heteroaryl group.

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

Z 1 to Z 3 in the structural formulas may be the same as or different from each other, and may be independently selected from groups defined for R 5 and R 6 of Chemical Formula 2.

In another exemplary embodiment of the present invention, one of R5 and R6 of Formula 2 may be a hydrogen atom, and both R5 and R6 may be hydrogen atoms.

L1 may be specifically selected from the group consisting of the following structural formulas, but is not limited thereto.

In the above description, the alkyl group preferably does not cause steric hindrance of 1 to 40 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

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

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

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

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

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

Examples of heterocyclic groups include pyridyl, bipyridyl, triazine, acridil, thiophene, furan, imidazole, oxazole, thiazole, triazole, quinolinyl and isoquinoline groups It is not limited only to these.

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

R 1 and R 2 are the same naphthyl, phenyl, biphenyl, carbazolyl substituted phenyl, phenanthryl, pyridyl substituted pyridyl, two phenyl substituted amino groups, pyridyl, pyrenyl, or isoquinolyl It is preferable.

L1 is preferably a direct bond, phenylene, naphthylene, pyridylene, biphenylene or thiylene.

R5 and R6 are preferably the same or different, phenyl, naphthyl, biphenyl, pyridyl substituted pyridyl, or vinyl substituted phenyl.

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

Hereinafter, a method for preparing the compound of Formula 1 will be described.

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

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

Specifically, the compound of Formula 1

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

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

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

[Reaction Scheme 1]

In addition, the compound of Formula 1

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

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

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

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

[Reaction Scheme 2]

In addition, a method for preparing an R 4 group corresponding to the substituent of Formula 2 will be described.

The R 4 group corresponding to the substituent of Formula 2 may be prepared by introducing an aryl substituent into the triazine derivative. Specifically, the compound of Formula 2 may be prepared by Grignard reaction of 1,3,5-triazine derivative, aryl magnesium halide derivative, or heteroaryl magnesium halide derivative in which a halide element is substituted at 2, 4, 6 positions. have.

Reactions other than the Grignard reaction among the methods used when preparing the R 4 group corresponding to the substituent of Formula 2 may use a general method known in the art.

Specifically, the R4 group corresponding to the substituent of Formula 2

1) preparing a triazine derivative substituted with R5 through a Grignard reaction of a triazine derivative substituted with a halogen group and a Grignard compound having an R5 substituent,

2) preparing a triazine derivative substituted with R5 and R6 through a Grignard reaction of a Grignard compound having an R6 substituent from the triazine derivative prepared in step 1);

3) a method of preparing triazine derivatives substituted with R5, R6 and L1 by suzuki-bonding boronic acid or boron ester compound substituted with L1 to the triazine derivative prepared in step 2) under a Pd catalyst; Manufacturing by, and

4) If necessary, the derivatives substituted R5, R6 and L1 prepared in step 3) may be prepared by a method comprising preparing a boron ester compound under a Pd catalyst.

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

Scheme 3

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

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

Hereinafter, the organic light emitting device will be described.

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

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

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

The organic material layer may be formed by using a variety of polymer materials in a smaller number of layers by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Can be manufactured.

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

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

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

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

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

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

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The 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.

Example

Manufacturing example  One

Synthesis of Compound of Formula 1-A

[Chemical Formula 1-A]

2-bromo-9,10-dinaphthylanthracene (5.00 g, 9.82 mmol), bis (pinacolato) diboron (2.75 g, 10.9 mmol) and potassium acetate (2.89 g, 29.4 mmol) were added to dioxane ( 50 mL). To the suspension was added palladium (diphenylphosphinoferrocene) chloride (0.24 g, 3 mol%). The resulting mixture was stirred at 80 ° C. for about 6 hours and cooled to room temperature. The mixture was diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mL). The organic extract was dried over magnesium sulfate and concentrated in vacuo. The crude product was washed with ethanol and dried in vacuo to give the compound of formula 1-A (5.46 g, 92%) which was 9,10-dinaphthylanthracenyl-2-borate.

MS: [M + H] ⁺ = 557

Synthesis of Compound of Formula 1-B

[Chemical Formula 1-B]

2,4,6-trichloro-1,3,5-triazine (20 g, 108.5 mmol) was dissolved in anhydrous tetrahydrofuran (50 mL), followed by 1 M phenylmagnesium bromide (228 mL, 227.8 mmol). It was slowly added dropwise at 占 폚. The temperature was raised to room temperature and then stirred for 4 hours. The remaining Grignard compound was removed with an aqueous solution of ammonium chloride (200 mL), neutralized with an aqueous solution of sodium bicarbonate (300 mL), and extracted with tetrahydrofuran (3 × 50 mL). Water was removed with anhydrous magnesium sulfate, followed by filtration. The excess was removed by distillation under reduced pressure of a solvent, and recrystallized with hexane to obtain a compound of Formula 1-B (15 g, 52%).

MS: [M + H] ⁺ = 268

Synthesis of Compound of Formula 1-1

[Formula 1-1]

After completely dissolving the compound of Formula 1-A (3.5 g, 8.0 mmol) and the compound of Formula 1-B (1.7 g, 6.3 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added thereto. 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 1-1 (1.5 g, 36%).

MS: [M + H] < ⁺ > = 662

Manufacturing example  2

Synthesis of Compound of Formula 2-A

[Chemical Formula 2-A]

After completely dissolving the compound of Formula 1-A (15 g, 27.9 mmol) and 3-bromophenol (4.5 g, 25.7 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added thereto and tetra Keystriphenylphosphinopalladium (626 mg, 0.54 mmol) was added thereto, followed by heating and stirring for 5 hours. The mixture was cooled to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and recrystallized with petroleum ether to obtain the compound of formula 2-A (13 g, 97%).

MS: [M + H] ⁺ = 523

Synthesis of Compound of Formula 2-B

[Chemical Formula 2-B]

The compound of formula 2-A (14 g, 26.8 mmol) was dissolved in dichloromethane, triethylamine (7.47 mL, 53.6 mmol) was added, followed by stirring for 10 minutes. After the temperature was lowered to 0 ° C., trifluoromethanesulfonic anhydride (4.4 mL, 40.2 mmol) was added slowly, and then the temperature was raised to room temperature, followed by stirring for 1 hour. After adding an aqueous sodium hydrogen carbonate solution, the water layer was removed and water was removed with anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, recrystallization with hexane to obtain the compound of formula 2-B (14.2 g, 81%).

MS: [M + H] ⁺ = 655

Synthesis of Compound of Formula 2-C

[Chemical formula 2-C]

The compound of Formula 2-C was obtained by the same method as the method of preparing Formula 1-A, except that Formula 2-B was used instead of 2-bromo-9,10-dinaphthylanthracene.

MS: [M + H] ⁺ = 633

Synthesis of Compound of Formula 2-D

[Chemical Formula 2-D]

2,4,6-trichloro-1,3,5-triazine (10 g, 54.2 mmol) was dissolved in anhydrous tetrahydrofuran (250 mL), then the temperature was lowered to 0 ° C. and 1 M phenylmagnesium bromine (54.2 mL) was added. After raising the temperature to room temperature and stirring for 2 hours, the temperature was lowered to 0 ° C. and 1 M 2-naphthyl magnesium bromide (54.2 mL) was added slowly, and then the temperature was raised to room temperature and stirred for 3 hours. The remaining Grignard compound was removed with an aqueous ammonium chloride solution (100 mL), neutralized with an aqueous sodium hydrogen carbonate solution (100 mL), and then extracted with tetrahydrofuran (3 × 50 mL). Water was removed with anhydrous magnesium sulfate, followed by filtration. The excess was removed by distillation under reduced pressure of a solvent, and then recrystallized with hexane to obtain the compound of formula 2-D (10.2 g, 59%).

MS: [M + H] ⁺ = 318

Synthesis of Compound of Formula 1-85

[Formula 1-85]

After completely dissolving the compound of Formula 2-C (5 g, 7.9 mmol) and the compound of Formula 2-D (2.1 g, 6.6 mmol) in tetrahydrofuran (80 mL), an aqueous 2 M potassium carbonate solution was added thereto. Tetrakis (triphenylphosphino) palladium (183 mg, 0.16 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 1-85 (4.1 g, 79%).

MS: [M + H] ⁺ = 788

Manufacturing example  3

Synthesis of Compound of Formula 3-A

[Formula 3-A]

The compound of Chemical Formula 3-A was prepared by the same method as the method of preparing Chemical Formula 1-A, except that 2-bromo-6-naphthol was used instead of 2-bromo-9,10-dinaphthylanthracene. .

MS: [M + H] ⁺ = 271

Synthesis of Compound of Formula 3-B

[Formula 3-B]

After completely dissolving the compound of Formula 3-A (9 g, 33.3 mmol) and the compound of Formula 1-B (7.43 g, 27.8 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (644 mg, 0.56 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 recrystallized with hexane to prepare the compound of Chemical Formula 3-B (8.2 g, 79%).

MS: [M + H] ⁺ = 376

Synthesis of Compound of Formula 3-C

[Formula 3-C]

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

MS: [M + H] ⁺ = 488

Synthesis of Compound of Formula 1-217

[Formula 1-217]

After completely dissolving the compound of Formula 1-A (5 g, 9.0 mmol) and the compound 3-C (3.6 g, 7.5 mmol) in tetrahydrofuran (100 mL), 2 M aqueous potassium carbonate solution is added and tetra Keystriphenylphosphinopalladium (173 mg, 0.15 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 purified by column purification to recrystallize the compound of Chemical Formula 1-217 (3.0 g, 51%).

MS: [M + H] ⁺ = 788

Manufacturing example  4

Synthesis of Compound of Formula 4-A

[Formula 4-A]

The compound of Formula 4-A was prepared by the same method as the method of preparing Formula 1-A, except that 1-bromo-4-phenol was used instead of 2-bromo-9,10-dinaphthylanthracene. .

MS: [M + H] ⁺ = 221

Synthesis of Compound of Formula 4-B

[Formula 4-B]

After completely dissolving the compound of Formula 4-A (9 g, 40.9 mmol) and the compound of Formula 1-B (9.1 g, 34.1 mmol) in tetrahydrofuran (400 mL), 2 M aqueous potassium carbonate solution was added and tetra Keystriphenylphosphinopalladium (790 mg, 0.68 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 recrystallized with hexane to prepare the compound of Chemical Formula 4-B (7.1 g, 64%).

MS: [M + H] ⁺ = 326

Synthesis of Compound of Formula 4-C

[Formula 4-C]

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

MS: [M + H] ⁺ = 438

Synthesis of Compound of Formula 1-145

After completely dissolving the compound of Formula 1-A (5 g, 9.0 mmol) and the compound 4-C (3.3 g, 7.5 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added thereto and tetrakis Triphenylphosphinopalladium (174 mg, 0.15 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 column purified to prepare the compound of Chemical Formula 1-145 (3.3 g, 60%).

MS: [M + H] ⁺ = 738

Synthesis of Compound of Formula 1-433

[Formula 1-433]

After completely dissolving the compound of Formula 2-C (5 g, 7.9 mmol) and the compound 4-C (2.9 g, 6.6 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added and tetrakis Triphenylphosphinopalladium (153 mg, 0.13 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 column purified to prepare the compound of Chemical Formula 1-433 (2.9 g, 54%).

MS: [M + H] ⁺ = 815

Manufacturing example  5

Synthesis of Compound of Formula 5-A

[Formula 5-A]

Carbazole (3.3 g, 20 mmol), 1-bromo-4-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 were refluxed under a nitrogen atmosphere. After cooling to room temperature, the product was extracted with ethyl acetate, water was removed with anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. After passing through a silica gel column using a hexane solvent to obtain a compound, the solvent was removed under reduced pressure and dried under vacuum to prepare the compound of formula 5-A (1.6 g, 25%) as a white solid.

MS: [M + H] ⁺ = 322

Synthesis of Compound of Formula 5-B

[Formula 5-B]

The compound of formula 5-A (4.38 g, 13.2 mmol) was dissolved in dry tetrahydrofuran (80 mL) under nitrogen atmosphere. The solution was cooled to -78 ° C and n-butyl lithium (6.6 mL, 2.5 M hexane solution) was slowly added to the cooled solution over 10 minutes and then stirred at -78 ° C for about 40 minutes. 2-Bromoanthraquinone compound (3.59 g, 5.5 mmol) was added to the reaction mixture and further stirred at −78 ° C. for about 3 hours. The mixture was stirred at rt for about 1 h. To the mixture was added aqueous ammonium chloride solution (50 mL). The organic layer was separated and the aqueous layer was extracted with diethyl ether (60 mL). The extracted organic solution layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained solid was suspended with diethyl ether, stirred for 1 hour and then filtered. After drying, a compound of formula 5-B (3.32 g, 73%) was prepared as a dialcohol compound.

MS [M + H] ⁺ = 773

Synthesis of Compound of Formula 5-C

[Formula 5-C]

The compound of formula 5-B (2.82 g, 3.65 mmol) was added to a dispersion of acetic acid (60 mL), potassium iodide (3.32 g, 20 mmol) and sodium hypophosphite hydrate (3.52 g, 40 mmol). The mixture was refluxed for about 3 hours with continued stirring and then cooled to room temperature. The mixture was filtered, washed with water and dried in vacuo to give the compound of formula 5-C (2.87 g, 90%).

MS: [M + H] ⁺ = 739

Synthesis of Compound of Formula 5-D

[Formula 5-D]

Except for using the compound of Formula 5-C instead of 2-bromo-9,10-dinaphthylanthracene and bis (pinacolato) diboron in the method for preparing the compound of Formula 1-A of Preparation Example 1 Was prepared in the same manner as the method for preparing the compound of Formula 1-A.

MS [M + H] ⁺ = 787

Synthesis of Compound of Formula 1-149

[Formula 1-149]

After completely dissolving the compound of Formula 5-D (5 g, 6.4 mmol) and the compound of Formula 4-C (2.3 g, 5.3 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added thereto. Tetrakistriphenylphosphinopalladium (123 mg, 0.11 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 purified by column purification to recrystallize to obtain the compound of Chemical Formula 1-149 (2.7 g, 53%).

MS: [M + H] ⁺ = 969

Manufacturing example  6

Synthesis of Compound of Formula 6-A

[Formula 6-A]

Dissolve 1-bromonaphthalene (34.8 g, 168.2 mmol) in tetrahydrofuran (170 ml), lower the temperature to -78 ° C and slowly add n-butyllithium (67.3 ml, 168,2 mmol) for 1 hour. Was stirred. 2-bromoanthraquinone (21 g, 73.1 mmol) was added and the temperature was raised to room temperature and stirred for 3 hours. Aqueous solution of saturated ammonium chloride was added thereto, the water layer was removed, dried over anhydrous magnesium sulfate, filtered and dried under reduced pressure. Recrystallization with ethyl ether and petroleum ether to prepare the compound of formula 6-A (32.3 g, 82%).

MS: [M + H] ⁺ = 544

Synthesis of Compound of Formula 6-B

[Formula 6-B]

The compound of Chemical Formula 6-A (32.3 g, 59.5 mmol), potassium iodide (29.6 g, 178.4 mmol), sodium hypophosphite (38 g, 256.8 mmol) was added to acetic acid (40 mL), and the mixture was heated and stirred for 3 hours at room temperature. After lowering the temperature, the precipitate was filtered and recrystallized with ethanol to prepare the compound of Chemical Formula 6-B (25.5 g, 84%).

MS: [M + H] ⁺ = 509

Synthesis of Compound of Formula 6-C

[Formula 6-C]

Method for synthesizing the compound of Formula 1-A, except that Formula 6-B was used instead of 2-bromo-9,10-dinaphthylanthracene in the synthesis of Compound 1-A of Preparation Example 1 Synthesis was carried out in the same manner as to prepare a compound of Chemical Formula 6-C.

MS: [M + H] ⁺ = 557

Synthesis of Compound of Formula 1-219

[Formula 1-219]

After completely dissolving the compound of Formula 6-C (5 g, 9.0 mmol) and the compound of Formula 3-C (3.6 g, 7.5 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added thereto. Tetrakistriphenylphosphinopalladium (174 mg, 0.15 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 purified by column purification to recrystallize the compound of Chemical Formula 1-219 (4.1 g, 69%).

MS: [M + H] ⁺ = 789

Manufacturing example  7

Synthesis of Compound of Formula 7-A

[Formula 7-A]

A compound of Chemical Formula 6-A was synthesized except that 1-bromo-4- (2-naphthyl) benzene was used instead of 1-bromonaphthalene in the synthesis of Chemical Formula 6-A of Preparation Example 6. In the same manner as one method to prepare a compound of Formula 7-A.

MS: [M + H] ⁺ = 696

Synthesis of Compound of Formula 7-B

[Formula 7-B]

Except for using the compound of Formula 7-A instead of the compound of Formula 6-A in the synthesis of the compound of Formula 6-B of Preparation Example 6 in the same manner as the method of synthesizing the compound of Formula 6-B The compound of Formula 7-B was prepared.

MS: [M + H] ⁺ = 661

Synthesis of Compound of Formula 7-C

[Formula 7-C]

A compound of Chemical Formula 1-A was synthesized except that the compound of Chemical Formula 7-B was used instead of 2-bromo-9,10-dinaphthylanthracene in the synthesis of Chemical Formula 1-A of Preparation Example 1 In the same manner as one method to prepare a compound of Formula 7-C.

MS: [M + H] ⁺ = 709

Synthesis of Compound of Formula 1-222

[Formula 1-222]

After completely dissolving the compound of Formula 7-C (5 g, 7.1 mmol) and the compound 3-C (2.9 g, 5.9 mmol) in tetrahydrofuran (100 mL), an aqueous 2 M potassium carbonate solution was added thereto and tetrakis Triphenylphosphinopalladium (137 mg, 0.12 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 purified by column purification to recrystallize the compound of Chemical Formula 1-222 (2.6 g, 47%).

MS: [M + H] ⁺ = 941

Experimental Example  One

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

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

[LINE]

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

[NPB]

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

[Alq ₃ ]

The compound of Formula 1-85 prepared in Preparation Example 1 was vacuum deposited to a thickness of 200 kPa on the light emitting layer to form an electron injection and transport layer.

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.

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

As a result of applying a forward electric field of 6.0 V to the organic light emitting device, green light corresponding to x = 0.37, y = 0.55 was observed based on 1931 CIE color coordinate at a current density of 50 mA / cm 2, and 7.1 V of When the forward electric field was applied, green light of 2.75 cd / A was observed at a current density of 100 mA / cm 2.

Experimental Example  2

Hexanitrile hexaaza triphenylene (500 Hz), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) on an ITO electrode prepared in the same manner as in Example 1 (400 kPa), Alq ₃ (300 kPa), and compounds of formula 1-217 (200 kPa) were sequentially vacuum-deposited to form a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer in that order.

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

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

When a forward electric field of 6.2 V was applied to the organic light emitting device manufactured above, green light corresponding to x = 0.39 and y = 0.58 was observed based on 1931 CIE color coordinate at a current density of 50 mA / cm 2, and 7.5 V of When the forward electric field was applied, green light of 2.62 cd / A was observed at a current density of 100 mA / cm 2.

Experimental Example  3

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

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

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

As a result of applying a forward electric field of 7.1 V to the organic light emitting device manufactured above, blue light corresponding to x = 0.20 and y = 0.24 was observed based on 1931 CIE color coordinate at a current density of 50 mA / cm 2, and 7.8 V When a forward electric field was applied, blue light of 2.0 cd / A was observed at a current density of 100 mA / cm 2.

Experimental Example  4

Hexanitrile hexaazatriphenylene (500 Å), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400 Å) on the ITO electrode prepared in Experimental Example 1 ), And the compound of formula 1-219 (300 Å), Alq ₃ (200 Å), lithium fluoride (LiF) 12 순차적 sequentially vacuum evaporation hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron Injection layers were formed in turn. 2000 nm thick aluminum was deposited thereon to form a cathode to manufacture an organic light emitting device.

As a result of applying a forward electric field of 6.3 V to the organic light emitting device, green light corresponding to x = 0.34 and y = 0.59 was observed based on a 1931 CIE color coordinate at a current density of 50 mA / cm 2. In addition, when a forward electric field of 7.3 V was applied, green light of 3.8 cd / A was observed at a current density of 100 mA / cm 2.

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

Claims (21)

A compound of formula
[Formula 1]

In Formula 1,
R1 and R2 are the same as or different from each other, independently halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ alkoxy group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ of the heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or unsubstituted C ₆ ~ C ₄₀ aryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or selected from the group consisting of an aryl amine of the unsubstituted C ₆ ~ C ₄₀ ,
At least one of R3 and R4 is a group of formula (2),
(2)

In Chemical Formula 2,
R5 and R6 are the same or different from each other and represent hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ amino group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or or selected from the group consisting of a heteroaryl unsubstituted C ₅ ~ C ₄₀ , To form a condensed ring of aliphatic, aromatic, heteroaliphatic or heteroaromatic with adjacent groups or to form a spiro bond,
L1 is a direct bond; A C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl group, a C ₂ -C ₄₀ alkynyl group of, C ₁ -C ₄₀ alkoxy group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ C ₂ -C ₄₀ alkenylene group unsubstituted or substituted with one or more groups selected from the group consisting of a heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group of the aryl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and a C ₅ ~ heteroaryl group of C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting or unsubstituted substituted group unsubstituted C for ₆ ~ C ₄₀ aryl amine, or unsubstituted C ₅ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₂₅ -C ₄₀ spiro group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ Is selected from the group consisting of C ₂₅ ~ C ₄₀ open spiro group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group, Substituted or unsubstituted C ₆ ~ C ₄₀ arylene group, except for the anthracene connected to the 9, 10 position, the two arylene groups are connected,
A group other than the group represented by the formula (2) in R3 and R4 is hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, a heteroaryl group of C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₅ ~ C _40; And C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C _It is selected from the group consisting of C ₆ ~ C ₄₀ arylamine group unsubstituted or substituted with one or more groups selected from the group consisting of ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group. The compound of claim 1, wherein R 1 and R 2 in Formula 1 are the same aryl group. The compound of claim 1, wherein R 1 and R 2 in Formula 1 are the same heteroaryl group. The compound of claim 1, wherein R 1 and R 2 of Formula 1 are amino groups substituted with the same aryl group or heteroaryl group. The compound of claim 1, wherein R 1 and R 2 of Formula 1 are selected from the group consisting of the following structural formulas:

Z 1 to Z 3 in the structural formulas are the same as or different from each other, and hydrogen; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ A C ₃ -C ₄₀ amino group unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ a heterocycloalkyl group, an aryl group, a C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the group consisting of heteroaryl or unsubstituted C ₆ ~ C _40; And halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of a group is selected from the group consisting of a heteroaryl unsubstituted C ₅ ~ C ₄₀ of Can be. The compound of claim 1, wherein R 5 and R 6 in Formula 2 are the same aryl group. The compound of claim 1, wherein R 5 and R 6 in Formula 2 are the same heteroaryl group. The compound of claim 1, wherein R5 and R6 of Formula 2 are amino groups substituted with the same aryl group or heteroaryl group. The compound of claim 1, wherein at least one of R5 and R6 of Formula 2 is hydrogen. The compound of claim 1, wherein R 5 and R 6 of Formula 2 are hydrogen. The compound of claim 1, wherein L 1 of Chemical Formula 2 is selected from the group consisting of the following structural formulas.

The method according to claim 1, wherein the alkyl group is a methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, hexyl group or heptyl group, the cycloalkyl group is cyclopentyl group or cyclohexyl group, The alkenyl group is a stilbenyl group or styrenyl group, the aryl group is a phenyl group, naphthyl group, anthracenyl group, biphenyl group, pyrenyl group or perylene group, and the aryl amine group is phenylamine, naph Tylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine, diphenyl amine group, phenyl naphthyl Amine group, ditolyl amine group, phenyl tolyl amine group, carbazole or triphenyl amine group, and the heterocyclic group is a pyridyl group, bipyridyl group, acridil group, thiophene group, furan group, imidazole group, oxazole group , Thiazole group, triazole group, quinolinyl group or A compound bovine quinoline group, and that of the halogen group is fluorine, chlorine, bromine or iodine. The substituted C ₂ -C ₄₀ alkenylene group of claim 1, wherein the substituted C ₂ -C ₄₀ alkenylene group is C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₁ -C ₄₀ alkoxy A compound substituted with at least one group selected from the group consisting of a group, a C ₆ -C ₄₀ aryl group and a C ₃ -C ₄₀ heteroaryl group. An organic electronic device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of claim 1 Electronic devices. The organic electronic device of claim 14, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor. The organic electronic device of claim 14, wherein the organic electronic device is an organic light emitting device. The organic electronic device of claim 16, wherein the organic light emitting device is an organic light emitting device having a forward structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. The organic electronic device of claim 16, wherein the organic light emitting device is an organic light emitting device having a reverse structure in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. The organic electronic device of claim 16, wherein the organic material layer of the organic light emitting device includes a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer. The organic electronic device of claim 16, wherein the organic material layer of the organic light emitting device comprises a light emitting layer, and the light emitting layer comprises the compound of claim 1. The organic electronic device of claim 16, wherein the organic material layer of the organic light emitting device includes an electron transport and / or injection layer, and the layer includes the compound of claim 1.

Images