KR20140091487A - Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same - Google Patents

Abstract

Disclosed are a compound for an organic electroluminescent device and an organic electroluminescent device including the same. Accordingly, provided are a compound for an organic electroluminescent device and an organic electroluminescent device, the compound having excellent electric stability and electron- and hole-transporting capabilities and being usable as a host which is capable of enhancing the luminous efficiency of phosphorescent and luminescent materials due to its high triplet-state energy and as an electron transporting material.

Description

TECHNICAL FIELD [0001] The present invention relates to a compound for a novel organic electroluminescent device and an organic electroluminescent device including the same. BACKGROUND OF THE INVENTION [0002]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic electroluminescent device and an organic electroluminescent device including the same, and more particularly to a compound for an organic electroluminescent device capable of improving the luminous efficiency of the organic electroluminescent device, Device.

As the move to the information society accelerates, the proportion of flat panel displays is gradually increasing. LCD (liquid crystal display) is the most widely used method, but it is a method to make a screen by applying voltage to liquid crystal and passing light from backlight through color filter to obtain three primary colors. Organic light emitting diodes (OLED) As a self-luminous element, it has excellent viewing angle and contrast ratio, is lightweight and thin, can be used for a substrate having a bending property, and is capable of transparent and flexible display, and has attracted attention as a next generation display element.

Organic EL is a phenomenon in which excitons are formed by recombination of electrons and holes injected through a cathode and an anode into an organic thin film, and light of a specific wavelength is generated from the excitons formed. In 1963, Pope et al. Reported that an anthracene single crystal (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, No. 913p, 1987) by Eastman Kodak Co., Ltd. (CW Tang) et al.

Organic materials used in organic electroluminescent devices are classified into polymer and small molecule, and small molecules can be divided into pure organic material and metal complex which forms metal and chelate.

Polymers can combine diverse functional units into polymer chains to produce multifunctional materials. However, it is difficult to purify compounds or to form devices, while low-molecular materials can synthesize materials of various properties. There is a limit to the synthesis of the substances.

The organic electroluminescent device can be formed in a laminated structure. In general, the device structure is formed by forming a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer between an anode and a cathode to form a light emitting layer It is possible to facilitate the formation of excitons and increase the luminous efficiency.

The luminescent material can be roughly divided into a host material and a luminescent material (dopant) material, and the luminescent material is distinguished by fluorescence and phosphorescence depending on the luminescence mechanism.

The excited state of the electrons in the compound is 1: 3 ratio of singlet to triplet, and triplet state is generated about 3 times more. Thus, the internal quantum efficiency of phosphorescence falling from the triplet state to the base state is 75% while the internal quantum efficiency of the fluorescence falling from the singlet state to the ground state is only 25%. In addition, the theoretical limit of internal quantum efficiency reaches 100% when the interplanar transition from singlet state to triplet state occurs. A light emitting material that improves the light emitting efficiency by using this point is a phosphorescent material.

Due to the nature of organic materials, it is difficult to emit phosphorescence. As a phosphorescent material, transition metal (iridium) is utilized as an organometallic compound, and an organic material is used as a host material to assist it. The material that assists the phosphorescent material (host) should have a wide bandgap and a high half-energy state energy. A phosphorescent material having excellent current efficiency and luminous efficiency is received in the spotlight, but the electron transporting ability, the hole transporting ability, the host material which is thermally and electrically stable, and the organic electroluminescent device It is necessary to develop a compound for use.

The present invention relates to a compound capable of being used for a light emitting layer as a host which is excellent in electrical stability, electron and hole transporting ability, and has high triplet state energy and can improve the luminous efficiency of a phosphorescent light emitting material, A light emitting element can be provided.

In addition, the present invention can provide an organic electroluminescent compound that can be used for an electron transporting material and a hole transporting material of an organic electroluminescent device, and an organic electroluminescent device including the same.

However, the problems to be solved by the present invention are not limited to the above-mentioned problems, and other problems not mentioned can be clearly understood by those skilled in the art from the following description.

According to an aspect of the present invention, a compound for an organic electroluminescence device represented by the following structural formula 1 may be provided.

[Structural formula 1]

In the above formula 1,

,

,

, 또는

이고,X ¹ represents an oxygen atom, a sulfur atom,

,

,

, or

ego,

Ar ¹ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ⁷ to R ¹¹ may be the same or different from each other, and R ⁷ to R ¹¹ each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,Y ¹ And Y ² may be the same or different from each other, and Y ¹ And Y < ² > are each independently a nitrogen atom, or

ego,

R ¹² represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ¹ to R ⁶ may be the same or different from each other and each of R ¹ to R ⁶ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

According to an embodiment of the present invention, preferably,

The organic electroluminescent device compound is represented by any one of the following structural formulas 2 to 4,

In the above Structural Formulas 2 to 4,

Ar ¹ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

이고,Y ¹ And Y ² may be the same or different from each other, and Y ¹ And Y < ² > are each independently a nitrogen atom, or

ego,

R ¹² represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ¹ to R ⁶ may be the same or different from each other and each of R ¹ to R ⁶ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C1 to C30 heteroaryl groups.

According to another embodiment of the present invention, preferably,

,

,

,

,

,

,

,

,

,

,

,

,

,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,R ¹ to R ⁴ , and R ¹² may be the same or different from each other, and R ¹ to R ⁴ and R ¹² are each independently a hydrogen atom,

,

,

,

,

,

,

,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,

, 또는

이고,X ² to X ⁹ may be the same or different from each other, and each of X ² to X ⁹ independently represents an oxygen atom, a sulfur atom,

, or

ego,

Ar ² represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ⁵⁷ and R ⁵⁸ may be the same or different from each other, and R ⁵⁷ and R ⁵⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,Y ³ To Y ¹⁶ may be the same or different from each other, and Y ³ To Y ¹⁶ each independently represents a nitrogen atom, or

ego,

R ⁵⁹ represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ¹³ to R ⁵⁶ may be the same or different from each other, and each of R ¹³ to R ⁵⁶ independently represents a hydrogen atom, a silyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Or an unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

According to another embodiment of the present invention, preferably,

,

,

,

,

,

,

,

,

,

,

,

,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,R ¹³ to R ⁵⁶ may be the same or different from each other, and R ¹³ to R ⁵⁶ each independently represent a hydrogen atom,

,

,

,

,

,

,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,

Ar ³ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

, 또는

이고,X ¹⁰ to X ¹⁴ may be the same or different from each other, and X ¹⁰ to X ¹⁴ each independently represent an oxygen atom, a sulfur atom,

, or

ego,

Ar ⁴ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ¹⁰⁵ and R ¹⁰⁶ may be the same or different from each other, and each of R ¹⁰⁵ and R ¹⁰⁶ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

Y ¹⁷ And Y ¹⁸ may be the same or different from each other, and Y ¹⁷ And Y ¹⁸ are each independently a carbon atom or a silicon atom,

이고,Y ¹⁹ to Y ²³ may be the same or different from each other, Y ¹⁹ to Y ²³ each independently represent a nitrogen atom, or

ego,

R ¹⁰⁷ represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ⁶⁰ to R ¹⁰⁴ may be the same or different from each other, and each of R ⁶⁰ to R ¹⁰⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C1 to C30 heteroaryl groups.

According to another embodiment of the present invention, preferably,

,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,Ar ¹ is

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,

, 또는

이고,X ¹⁵ represents an oxygen atom, a sulfur atom,

, or

ego,

Ar ⁵ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ¹¹³ and R ¹¹⁴ may be the same or different from each other, and each of R ¹¹³ and R ¹¹⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ¹⁰⁸ to R ¹¹² may be the same or different from each other, and each of R ¹⁰⁸ to R ¹¹² independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C1 to C30 heteroaryl groups.

According to another embodiment of the present invention, preferably,

,

,

,

,

,

,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,R ⁵ and R ⁶ may be the same or different from each other, and R ⁵ and R ⁶ are each independently a hydrogen atom,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,

Ar ⁶ and Ar ⁷ may be the same or different from each other, Ar ⁶ and Ar ⁷ each independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

, 또는

이고,X ¹⁶ represents an oxygen atom, a sulfur atom,

, or

ego,

Ar ⁸ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ¹⁴¹ and R ¹⁴² may be the same or different from each other, and R ¹⁴¹ and R ¹⁴² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ¹¹⁵ to R ¹⁴⁰ may be the same or different from each other, and each of R ¹¹⁵ to R ¹⁴⁰ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C1 to C30 heteroaryl groups.

According to another embodiment of the present invention, preferably,

,

,

,

,

,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,Ar ⁶ and Ar ⁷ may be the same or different from each other, Ar ⁶ and Ar ⁷ are each independently

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,

Ar ⁹ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

, 또는

이고,X ¹⁷ and X ¹⁸ may be the same or different from each other, and X ¹⁷ and X ¹⁸ are each independently an oxygen atom, a sulfur atom,

, or

ego,

Ar ¹⁰ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,

R ¹⁶¹ and R ¹⁶² may be the same or different from each other, and R ¹⁶¹ and R ¹⁶² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,

이고,Y ²⁴ To Y ²⁶ may be the same or different from each other, and Y ²⁴ To Y < ²⁶ > each independently represent a nitrogen atom, or

ego,

R ¹⁶³ represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ¹⁴³ to R ¹⁶⁰ may be the same or different from each other, and each of R ¹⁴³ to R ¹⁶⁰ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C1 to C30 heteroaryl groups.

According to another embodiment of the present invention, preferably,

,

,

, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 시클로알킬기, 또는 치환 또는 비치환된 C1 내지 C30 헤테로시클로알킬기이고,R ¹¹⁵ to R ¹⁴⁰ may be the same or different from each other, and R ¹¹⁵ to R ¹⁴⁰ each independently represent a hydrogen atom,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,

이고,Y ²⁷ To Y ²⁹ may be the same or different from each other, and Y ²⁷ To Y ²⁹ each independently represent a nitrogen atom, or

ego,

R ¹⁷³ represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,

R ¹⁶⁴ to R ¹⁷² may be the same or different from each other and each of R ¹⁶⁴ to R ¹⁷² independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Substituted C1 to C30 heterocycloalkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C1 to C30 heteroaryl groups.

Examples of the substituted or unsubstituted C6 to C30 aryl group include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthalenyl group, a substituted or unsubstituted naphthalenyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted furanyl group, Lt; / RTI >

Examples of the substituted or unsubstituted C2 to C30 heteroaryl group include a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted thiophenyl group , A substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo [1,2-a] pyridinyl group, a substituted or unsubstituted A substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzoyl group, Substituted or unsubstituted imidazolyl groups, substituted or unsubstituted thiazolyl groups, substituted or unsubstituted tetrazolyl groups, substituted or unsubstituted oxadiazolyl groups, substituted or unsubstituted oxatriazolyl groups, However, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyridinyl group, Or a substituted or unsubstituted phenanthrolinyl group, preferably a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted aryidinyl group, a substituted or unsubstituted pyrazolinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, A substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzothiazolyl group, , A substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.

The compound for an organic electroluminescence device may be any one selected from compounds 1 to 441 represented by the following formulas.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound for an organic electroluminescent device.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode, The organic electroluminescent device may further include at least one organic compound layer including the organic electroluminescent compound.

The singular or plural organic layers may include a light emitting layer.

The plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer, and a hole injecting layer.

The light emitting layer may include a host and a dopant.

The present invention relates to a compound for an organic electroluminescent device which can be used for a light emitting layer as a host which is excellent in electrical stability and electron and hole transporting ability and has high triplet state energy and can improve the luminous efficiency of a phosphorescent light emitting material, An organic electroluminescent device can be provided.

In addition, the present invention can provide an organic electroluminescent compound which can be used for an electron transporting material and a hole transporting material of an organic electroluminescent device, and an organic electroluminescent device including the same.

1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view illustrating an organic electroluminescent device according to another embodiment of the present invention.

The invention is capable of various modifications and may have various embodiments, and particular embodiments are exemplified and will be described in detail in the detailed description. It is to be understood, however, that the invention is not to be limited to the specific embodiments, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

Furthermore, terms including an ordinal number such as first, second, etc. to be used below can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.

Also, when an element is referred to as being "formed" or "laminated" on another element, it may be directly attached or laminated to the front surface or one surface of the other element, It will be appreciated that other components may be present in the < / RTI >

The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

As used herein, "atomic bond" means a single bond, a double bond or a triple bond, unless otherwise defined.

As used herein, unless otherwise defined, "substituent" means that at least one hydrogen in the substituent or compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C30 silyl group, An alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C1 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, It means that it has been replaced by anger.

A C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 aryl group, a C1 to C30 aryl group, a C1 to C30 aryl group, An alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group may be fused to form a ring.

As used herein, unless otherwise defined, it is meant that one functional group contains 1 to 4 heteroatoms selected from the group consisting of N, O, S, and P, and the remainder is carbon.

In the present specification, the term "combination thereof" means that two or more substituents are bonded to each other via a linking group or two or more substituents are condensed and bonded.

As used herein, "hydrogen" means monohydrogen, double hydrogen, or tritium, unless otherwise defined.

As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group.

The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

The alkyl group may be an "unsaturated alkyl group" comprising at least one double bond or triple bond.

"Alkynylene group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynylene group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding. The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.

The alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group, a C1 to C10 alkyl group or a C1 to C6 alkyl group.

For example, the C1 to C4 alkyl groups may have 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.

The "amine group" includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.

"Cycloalkyl group" includes monocyclic or fused-ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

"Heterocycloalkyl group" means that the cycloalkyl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the remainder is carbon. When the heterocycloalkyl group is a fused ring, at least one ring of the fused rings may contain from 1 to 4 heteroatoms.

"An aromatic group" means a functional group in which all elements of a functional group in the form of a ring have a p-orbital, and these p-orbital forms a conjugation. Specific examples thereof include an aryl group and a heteroaryl group.

An "aryl group" includes a monocyclic or fused ring polycyclic (i. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

"Heteroaryl group" means that the aryl group contains 1 to 4 hetero atoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, at least one ring of the fused rings may contain from 1 to 4 heteroatoms.

In the aryl group and the heteroaryl group, the number of atoms in the ring is the sum of carbon number and non-carbon atom number.

When used in combination, such as "alkylaryl" or "arylalkyl group ", the terms alkyl and aryl of each of the above have the meanings and contents indicated above.

The term "arylalkyl group " means an aryl substituted alkyl radical, such as benzyl, and is included in the alkyl group.

The term "alkylaryl group " means an alkyl substituted aryl radical and is included in the aryl group.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT Hereinafter, embodiments of the present invention will be described with reference to the accompanying drawings. Referring to the accompanying drawings, the same or corresponding components are denoted by the same reference numerals, .

Referring to FIGS. 1 and 2, an organic electroluminescent device 1 including the compound for an organic electroluminescent device according to the present invention can be provided according to an embodiment of the present invention.

According to another embodiment of the present invention, the organic electroluminescent device includes a first electrode 110; A second electrode (150); And one or more organic layers 130 between the first and second electrodes and at least one organic layer selected from the single or plurality of organic layers 130 include the compound for an organic light emitting device according to the present invention can do.

Here, the single or plural organic layers 130 may include a light emitting layer 134.

The plurality of organic layers 130 may include a light emitting layer 134 and the plurality of organic layers may include an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, Transporting layer 136 and hole-injecting layer 137 may be further included.

The light emitting layer 134 may include a host and a dopant.

The organic electroluminescent device is preferably supported by a transparent substrate. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof include glass, transparent plastic film, and the like.

As the cathode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of 4 eV or more can be used. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO ₂ and ZnO, which are metals, can be mentioned. The thickness of the positive electrode film is preferably 10 to 200 nm.

As the anode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV may be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy and aluminum alloy can be mentioned. In addition, aluminum / AlO ₂ , aluminum / lithium, magnesium / silver or magnesium / indium may be used. The thickness of the negative electrode film is preferably 10 to 200 nm.

In order to increase the luminous efficiency of the organic EL device, at least one electrode preferably has a light transmittance of 10% or more. The sheet resistance of the electrode is preferably several hundreds? / Mm or less. The thickness of the electrode is 10 nm to 1 탆, more preferably 10 to 400 nm. Such an electrode can be manufactured by forming the electrode material into a thin film by a vapor deposition method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) or a sputtering method.

When the compound for an organic electroluminescence device of the present invention is used for the purpose of the present invention, the known hole transporting material, hole injecting material, light emitting layer material, host material of the light emitting layer, electron transporting material, Or may be used in combination with the organic electroluminescent device compound of the present invention selectively.

N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrenesulfonate (PEDOT: PSS), N, N'- (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'- diaminobiphenyl (TPD) N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N'N'N'N'- Porphyrin compound derivatives such as tetraphenyl-4,4'-diaminobiphenyl, copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin and the like, aromatic tertiary (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, phthalocyanine derivatives such as nonmetal phthalocyanine and copper phthalocyanine, An aminostilbene derivative, a derivative of an aromatic tertiary amine and a styrylamine compound, and polysilane.

The diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq 3, 2,5- diaryl silole derivatives (PyPySPyPy), perfluoro rineyi suited compound (PF-6P), Octasubstituted cyclooctatetraene compound (COTs) as an electron transport material .

In the organic electroluminescent device of the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be formed of a single layer containing at least one kind of the above-mentioned compounds, And the like.

Examples of the light emitting material include a phosphorescent fluorescent material, a fluorescent whitening agent, a laser dye, an organic scintillator, and a reagent for fluorescence analysis. Specifically, a carbazole compound, a phosphine oxide compound, a carbazole-based phosphine oxide compound, bis (3,5-difluoro-4-cyanophenyl) pyridine, iridium picolinate (FCNIrpic), tris (8-hydroxyquinoline) aluminum Alq ₃ ), polyaromatic compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, 1,4- Bis (4-methylstyryl) benzene, 1,4-bis (4-methyl- Bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, 1,6- Liquid scintillation scintillators such as 3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, dicyanomethylenepyran dyes, dicyanomethylene Cyopyran pigment, polymethine pigment, oxobenzanthracene There may be mentioned a colorant, a xanthene colorant, a carbostyryl colorant, a perylene colorant, an oxazine compound, a stilbene derivative, a spiro compound, and an oxadiazole compound.

Each layer constituting the organic EL device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be manufactured using a material used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected according to the characteristics of the material, but may be determined usually in the range of 2 nm to 5,000 nm.

The compound for an organic electroluminescence device according to the present invention can be formed by a vacuum deposition method, so that it is advantageous that a thin film forming process is simple and a homogeneous thin film having almost no pinhole can be easily obtained.

 [Example]

Hereinafter, the compound for an organic electroluminescent device according to the present invention and the method for manufacturing the organic electroluminescent device including the same will be described in more detail with reference to the following examples. However, this is for the purpose of illustration only and is not intended to limit the scope of the invention.

Example  1: Synthesis of compound 1

(One) Manufacturing example  1-1: Intermediate 1-1 Synthesis

2,7-dibromophenanthrene (10.5 g, 0.032 mol / sigma Aldrich) was placed under 200 ml of hexane. TMEDA (24ml, 0.16mol / Sigma Aldrich), n-BuLi (1.6M, 100ml, 0.16mol) was placed through the dropping funnel. After stirring for 3 hours under N ₂ , S2Cl2 (6.4 ml, 0.08 mol / Sigma Aldrich) was slowly added and reacted at room temperature for 24 hours. The reaction mixture was cooled, layered under H ₂ O: methylene chloride (MC), and subjected to column purification (n-hexane: methylene chloride) to obtain 7.1 g (yield: 60%) of Intermediate 1-1.

LC / MS: m / z = 366 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  1-2: Compound 1 synthesis

Pd (PPh3) 4 (1.1 g, 0.001 mol / P & H TECH) and potassium carbonate (7.9 g, 0.057 mol) were added to Intermediate 1-1 (7.1 g, 0.019 mol) mol / Sigma Aldrich) was added 260 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.6 g (yield 67%) of Compound 1.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.41 / M, 8.34 / S, 7.71 / D, 8.10 / S) 4H (7.51 / M, 7.52 / D)

LC / MS: m / z = 361 [(M + 1) ^< ^{+ &}

Example  2: Synthesis of compound 2

2-ylboronic acid (8.0 g, 0.0465 mol / sigma Aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol), potassium carbonate (7.9 g, 0.057 mol ), 300 ml of THF was added, and the mixture was reacted at 65 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 5.3 g (yield: 61%) of Compound 2.

(7.59 / M, 8.00 / D): 1 H-NMR (200 MHz, CDCl ₃ ):? Ppm, 2H (7.92 / D, 7.73 / D, 7.58 /

LC / MS: m / z = 461 [(M + 1) ^< ^{+ &}

Example  3: Synthesis of compound 3

Pd (dba) 2 (0.9 g, 0.001 mol / p & h tech) and sodium tert-butoxide (5.5 g, 0.0465 mol) were added to Intermediate 1-1 (7.1 g, 0.019 mol) , 0.057 mol / sigma aldrich), and the mixture was reacted at 95 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 6.5 g (64%) of Compound 3.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.12 / D, 7.29 / M, 7.50 / M, 7.63 / D, 7.70 / D , 8.10 / S, 7.90 / S)

LC / MS: m / z = 539 [(M + 1) ^< ^{+ &}

Example  4: Synthesis of compound 4

Phenylboronic acid (14.6 g, 0.0465 mol / sigma Aldrich), Pd (PPh3) 4 (0.1 g, 0.019 mol) was added to Intermediate 1-1 1.1 g, 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 420 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 8.4 g (yield: 59%) of Compound 4.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.41 / M, 7.59 / D, 8.56 / D, 7.71 / D, 8.34 / S, 8.10 / S) 4H (7.22 / M, 7.51 / M, 8.28 / D, 7.79 / D, 7.68 / D)

LC / MS: m / z = 745 [(M + 1) ^< ^{+ &}

Example  5: Synthesis of compound 5

Dibenzo [b, d] thiophen-1-ylboronic acid (10.6 g, 0.0465 mol / Sigma Aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol), potassium carbonate (7.9 g, 0.057 mol), 340 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 6.1 g (yield: 56%) of Compound 5.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.50 / M, 7.94 / D, 7.56 / M, 7.98 / D, 7.52 / M, 7.71 / D, 7.82 / D, 8.45 / D, 8.34 / S , 8.10 / S)

LC / MS: m / z = 573 [(M + 1) ^< ^{+ &}

Example  6: Synthesis of Compound 6

4-ylboronic acid (12.8 g, 0.0465 mol / sigma Aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol), potassium carbonate (7.9 g, g, 0.057 mol), 400 ml of THF was added, and the mixture was reacted at 65 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 6.3 g (yield 50%) of Compound 6.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.10 / S, 8.34 / S, 7.71 / D) 4H (7.47 / M, 8.20 / S) 8H (7.54 / M, 8.30 / D)

LC / MS: m / z = 667 [(M + 1) ^< ^{+ &}

Example  7: Synthesis of Compound 7

Pd (PPh3) 4 (1.1 g, 0.001 mol), potassium carbonate (13.4 g, 0.0465 mol / Sigma Aldrich), 9-phenyl-9H-carbazol-2-ylboronic acid (7.1 g, 0.019 mol) (7.9 g, 0.057 mol), 400 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 7.1 g (yield: 54%) of Compound 7.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.45 / M, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 7.62 / S, 8.18 / D, 7.79 / D, 8.10 / S , 8.34 / S, 7.71 / D) 4H (7.50 / D, 7.58 / M)

LC / MS: m / z = 691 [(M + 1) ^< ^{+ &}

Example  8: Compound 8 Synthesis

3,5-diphenyl-4H-1,2,4-triazole (10.3 g, 0.0465 mol / sigma Aldrich) and Pd (dba) 2 (0.9 g, 0.001 mol) were added to Intermediate 1-1 (7.1 g, 0.019 mol) and sodium-tert-butoxide (5.5 g, 0.057 mol), and the mixture was reacted at 95 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 7.2 g (yield: 59%) of Compound 8.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.9 / S, 7.7 / D, 8.1 / S) 4H (7.41 / M) 8H (8.28 / D, 7.51 / M)

LC / MS: m / z = 647 [(M + 1) ^< ^{+ &}

Example  9: Synthesis of Compound 9

4- (3,5-diphenyl-4H-1,2,4-triazol-4-yl) phenylboronic acid (15.9 g, 0.0465 mol / sigma Aldrich), Pd pph3) 4 (1.1 g, 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 460 ml of THF and reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 8.5 g (yield: 56%) of Compound 9.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.10 / S, 8.34 / S, 7.71 / D) 4H (7.41 / M, 7.68 / D, 7.79 / D) 8H (8.28 / D) 7.51 / M )

LC / MS: m / z = 799 [(M + 1) ^< ^{+ &}

Example  10: Compound 10 Synthesis

Pyridine-2-ylboronic acid (13.4 g, 0.0465 mol / Sigma Aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 400 ml of THF and reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 7.8 g (yield: 59%) of Compound 10.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.12 / D, 7.29 / M, 7.50 / M, 7.63 / D, 7.38 / M , 7.26 / D, 7.50 / D, 8.61 / S, 8.85 / S, 7.71 / D)

LC / MS: m / z = 693 [(M + 1) ^< ^{+ &}

Example  11: Compound 11 Synthesis

(One) Manufacturing example  11-1: Intermediate 11-1 Synthesis

1,3,6,8-tetrabromophenanthrene (15.8 g, 0.032 mol / sigma Aldrich) is placed under 300 ml of hexane. Add TMEDA (24 ml, 0.16 mol) and n-BuLi (1.6 M, 100 ml, 0.16 mol) through the dropping funnel. After stirring for 3 hours under N ₂ , S ₂ Cl ₂ (6.4 ml, 0.08 mol) was slowly added and reacted at room temperature for 24 hours. The reaction mixture was cooled, layered under H ₂ O: methylene chloride (MC), and subjected to column purification (n-hexane: methylene chloride) to obtain 9.3 g (yield: 55%) of intermediate 11-1.

LC / MS: m / z = 524 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  11-2: Compound 11 Synthesis

To the intermediate 11-1 (9.3 g, 0.018 mol) was added 380 ml of THF to phenylboronic acid (10.5 g, 0.0864 mol), Pd (pph3) 4 (1.0 g, 0.0009 mol) and potassium carbonate (7.4 g, 0.054 mol) The mixture was stirred at 65 캜 for 4 hours to react. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.8 g (yield: 52%) of Compound 11.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.26 / S, 7.71 / D) 4H (7.41 / M) 8H (7.51 / M, 7.79 / D)

LC / MS: m / z = 513 [(M + 1) ^< ^{+ &}

Example  12: Compound 12 Synthesis

2-ylboronic acid (14.9g, 0.0864mol), Pd (PPh3) 4 (1.0g, 0.0009mol) and potassium carbonate (7.4g, 0.054mol) were added to intermediate 11-1 (9.3g, 0.018mol) And the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 8.1 g (yield: 63%) of Compound 12.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.26 / S, 7.71 / D) 4H (7.58 / S, 7.73 / D, 7.92 / D) 8H (8.00 / D, 7.59 / M)

LC / MS: m / z = 713 [(M + 1) ^< ^{+ &}

Example  13: Compound 13 Synthesis

Benzo [b] thiophen-2-ylboronic acid (15.4 g, 0.0864 mol / sigma aldrich), Pd (PPh3) 4 (1.0 g, 0.0009 mol), potassium carbonate (7.4 g, 0.054 mol), 480 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 8.4 g (yield: 63%) of Compound 13.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.26 / S, 7.71 / D) 4H (7.98 / D, 7.50 / M, 7.52 / M, 7.79 / D, 7.30 / S)

LC / MS: m / z = 738 [(M + 1) ^< ^{+ &}

Example  14: Compound 14 Synthesis

To the intermediate 11-1 (9.3 g, 0.018 mol) was added benzo [b] thiophen-2-ylboronic acid (15.4 g, 0.0864 mol), Pd (PPh3) 4 (1.0 g, 0.0009 mol) mol), 480 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain Compound (14) (10.8 g, yield 64%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.26 / S, 7.71 / D) 4H (7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D, 8.41 / D, 7.58 / M, 8.20 / D)

LC / MS: m / z = 938 [(M + 1) ^< ^{+ &}

Example  15: Compound 15 Synthesis

Benzo [d] phenanthro [9,10-b] thiophene-10-ylboronic acid (15.3 g, 0.0465 mol / sigma Aldrich), Pd (PPh3) 4 (1.1 g, 0.019 mol) 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 440 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 5.3 g (yield: 53%) of Compound 15.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.10 / S, 7.71 / D, 8.34 / S, 7.58 / M, 8.41 / D) 4H (8.93 / D, 7.88 / M, 7.82 / M, 8.12 / D)

LC / MS: m / z = 774 [(M + 1) ^< ^{+ &}

Example  16: Compound 16 Synthesis

(One) Manufacturing example  16-1: Synthesis of intermediate 16-1

4-ylboronic acid (5.2 g, 0.0228 mol / Sigma Aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol), potassium carbonate (7.9 g, 0.057 mol), 240 ml of THF was added, and the mixture was reacted at 65 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 5.3 g (yield: 59%) of intermediate 16-1.

LC / MS: m / z = 470 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  16-2: Compound 16 Synthesis

2-ylboronic acid (3.1 g, 0.0132 mol / sigma Aldrich) and Pd (PPh3) 4 (0.6 g, 0.0006 mol) were added to Intermediate 16-1 (5.3 g, 0.011 mol) ) and potassium carbonate (4.5 g, 0.033 mol) were added 160 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 3.8 g (yield: 59%) of Compound 16.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 8.56 / D, 7.59 / D, 8.20 / M, 8.41 / D, 8.45 / D, 7.52 / M, 7.50 / M, 7.98 / D ) 2H (7.71 / D, 8.34 / S, 7.22 / M, 8.10 / S, 7.50 / D)

LC / MS: m / z = 583 [(M + 1) ^< ^{+ &}

Example  17: Compound 17 Synthesis

D] imidazol-2-ylboronic acid (5.3 g, 0.0132 mol / sigma Aldrich) was added to Intermediate 16-1 (5.3 g, 0.011 mol) , Pd (pph3) 4 (0.6 g, 0.0006 mol) and potassium carbonate (4.5 g, 0.033 mol) were added 200 ml of THF and reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 5.1 g (yield: 62%) of Compound 17.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / M, 8.41 / D, 8.45 / D, 7.52 / M, 7.50 / M, 7.98 / D, 8.20 / D, 7.59 / D, 7.15 / D , 7.63 / D, 7.50 / M, 7.29 / M, 8.12 / D, 8.55 / D, 7.25 / M, 7.33 / M, 7.94 / D, 7.70 / , 7.50 / D) 3H (7.58 / M)

LC / MS: m / z = 748 [(M + 1) ^< ^{+ &}

Example  18: Compound 18 Synthesis

(One) Manufacturing example  18-1: Synthesis of Intermediate 18-1

Tert-butoxide (5.5 g, 0.057 mol) was added to 9 g of Intermediate 1-1 (7.1 g, 0.019 mol) in the presence of 9H-carbazole (3.8 g, 0.0228 mol), Pd (dba) And the mixture was reacted at 95 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 5.3 g (yield: 62%) of Intermediate 18-1.

LC / MS: m / z = 453 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  18-2: Compound 18 Synthesis

2-ylboronic acid (5.3 g, 0.0132 mol / sigma Aldrich), Pd (PPh3) 4 (0.6 g, 0.0006 mol) and potassium carbonate (4.5 g, 0.033 mol) were added to Intermediate 18-1 ), 200 ml of THF was added and the mixture was reacted at 65 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.7 g (yield: 58%) of Compound 18.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.70 / S, 8.30 / S, 7.90 / S, 7.15 / D, 7.59 / D, 7.45 / M) 2H (7.58 / M, 7.70 / D, 7.50 D, 7.50 / M, 7.29 / M, 8.12 / D, 7.63 / D, 8.55 / D, 7.25 / M, 7.33 /

LC / MS: m / z = 731 [(M + 1) ^< ^{+ &}

Example  19: Compound 19 Synthesis

(One) Manufacturing example  19-1: Synthesis of intermediate 19-1

Phenylboronic acid (8.3 g, 0.0228 mol / sigma Aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol) was added to Intermediate 1-1 (7.1 g, 0.019 mol) mol) and potassium carbonate (7.9 g, 0.057 mol) were added 300 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 6.6 g (yield: 58%) of Intermediate 19-1.

LC / MS: m / z = 604 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  19-2: Compound 19 Synthesis

4,6-diphenyl-1,3,5-triazin-2-ylboronic acid (3.7 g, 0.0132 mol / sigma Aldrich) and Pd (PPh3) 4 (0.6 g, 0.011 mol) were added to Intermediate 19-1 0.0006 mol) and potassium carbonate (4.5 g, 0.033 mol) were added 200 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 3.8 g (yield: 46%) of Compound 19.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.26 / M) 2H (7.29 / D, 7.28 / M, 7.38 / M, 7.87 / D, 7.11 / D, 7.55 / D, 8.10 / S, 8.34 7.41 / M, 7.33 / D) 4H (8.28 / D, 7.51 / M)

LC / MS: m / z = 756 [(M + 1) ^< ^{+ &}

Example  20: Compound 20 Synthesis

Phenylboronic acid (16.7 g, 0.0465 mol), Pd (PPh3) 4 (1.1 g, 0.001 mol), 4- (9-phenyl-9H- Potassium carbonate (7.9 g, 0.057 mol) was added with 460 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 10.9 g (yield: 68%) of Compound 20.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.63 / D, 7.93 / D, 7.87 / D, 7.38 / M, 7.28 / M, 8.10 / S, 8.34 / S, 7.71 / D) 4H (7.26 / M, 7.55 / D) 8H (7.11 / D, 7.33 / M)

LC / MS: m / z = 842 [(M + 1) ^< ^{+ &}

Example  21: Compound 21 Synthesis

(One) Manufacturing example  21-1: Synthesis of Intermediate 21-1

2-bromophenanthrene (8.2 g, 0.032 mol / sigma Aldrich) is placed under 160 ml of hexane. Add TMEDA (24 ml, 0.16 mol) and n-BuLi (1.6 M, 100 ml, 0.16 mol) through the dropping funnel. N ₂ , S ₂ Cl ₂ (6.4 ml, 0.08 mol) was added slowly, and the reaction was allowed to proceed at room temperature for 24 hours. The reaction mixture was cooled, layered under H ₂ O: methylene chloride (MC), and subjected to column purification (n-hexane: methylene chloride) to obtain 5.4 g (yield: 59%) of Intermediate 21-1.

LC / MS: m / z = 287 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  21-2: Compound 21 Synthesis

(Dibenzo [b, d] thiophen-4-yl) phenylboronic acid (6.9 g, 0.0228 mol / Sigma Aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 220 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.6 g (yield: 52%) of Compound 21.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.10 / S, 8.34 / S, 7.88 / D, 7.82 / M, 8.12 / D, 7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D , 8.41 / D, 7.58 / M, 8.20 / D) 2H (7.71 / D)

LC / MS: m / z = 467 [(M + 1) ^< ^{+ &}

Example  22: Compound 22 Synthesis

Phenylboronic acid (7.2 g, 0.0228 mol / sigma Aldrich), Pd (PPh3) 4 (5.4 g, 0.019 mol) 1.1 g, 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 240 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 5.9 g (yield: 65%) of Compound 22.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.56 / D, 7.45 / M, 7.59 / D, 8.10 / S, 8.34 / S, 7.88 / D, 7.82 / M, 8.12 / D) 2H (7.25 / D, 7.85 / D, 7.50 / D, 7.58 / M, 7.22 / M, 7.71 / D)

LC / MS: m / z = 477 [(M + 1) ^< ^{+ &}

Example  23: Compound 23 Synthesis

(One) Manufacturing example  23-1: Synthesis of Intermediate 23-1

3,8-dibromo-4,7-phenanthroline (10.8 g, 0.032 mol / sigma Aldrich) is placed under 200 ml of hexane. Add TMEDA (24 ml, 0.16 mol) and n-BuLi (1.6 M, 100 ml, 0.16 mol) through the dropping funnel. After stirring for 3 hours under N ₂ , S ₂ Cl ₂ (6.4 ml, 0.08 mol) was slowly added and reacted at room temperature for 24 hours. The reaction mixture was cooled, layered under H ₂ O: methylene chloride (MC), and subjected to column purification (n-hexane: methylene chloride) to obtain 7.0 g (yield: 59%) of Intermediate 23-1.

LC / MS: m / z = 368 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  23-2: Compound 23 Synthesis

220 ml of THF was added to intermediate 23-1 (7.0 g, 0.019 mol), phenylboronic acid (5.7 g, 0.0465 mol), Pd (pph3) 4 (1.1 g, 0.001 mol) and potassium carbonate (7.9 g, C < / RTI > for 4 hours. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 4.5 g of Compound 23 (yield 65%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.47 / M, 7.42 / S, 7.76 / D) 4H (8.30 / D, 7.54 / M)

LC / MS: m / z = 363 [(M + 1) ^< ^{+ &}

Example  24: Compound 24 Synthesis

2-boronobenzo [b] thiophen-6-ylium (8.0 g, 0.0465 mol), Pd (PPh3) 4 (1.1 g, 0.001 mol), potassium carbonate (7.9 g, 0.057 mol), 300 ml of THF was added, and the mixture was reacted at 65 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.9 g (yield: 54%) of Compound 24.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.98 / D, 7.50 / M, 7.52 / M, 7.79 / D, 7.30 / S, 7.76 / D, 7.48 / S)

LC / MS: m / z = 475 [(M + 1) ^< ^{+ &}

Example  25: Compound 25 Synthesis

To the intermediate 23-1 (7.0 g, 0.019 mol), 9H-carbazole (7.8 g, 0.0465 mol), Pd (dba) 2 (0.9 g, 0.001 mol) and sodium tert- And the mixture was reacted at 95 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 5.7 g (yield: 55%) of Compound 25.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.63 / D, 7.50 / M, 7.29 / M, 8.12 / D, 8.55 / D, 7.25 / M, 7.33 / M, 7.94 / D, 7.30 / S , 7.76 / D)

LC / MS: m / z = 541 [(M + 1) ^< ^{+ &}

Example  26: Compound 26 Synthesis

1-phenyl-3a, 7a-dihydro-1H-benzo [d] imidazol-2-ylboronic acid (11.2 g, 0.0465 mol) and Pd (PPh3) 4 (1.1 g , 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 360 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 6.0 g of Compound 26 (yield: 53%).

(7.50 / D, 7.22 / M, 7.58 / M): 1 H-NMR (200 MHz, CDCl ₃ ):? Ppm, 2H (7.48 / S, 7.76 / D, 8.56 / D, 7.59 / D, 7.45 /

LC / MS: m / z = 595 [(M + 1) ^< ^{+ &}

Example  27: Compound 27 Synthesis

Phenylboronic acid (14.6 g, 0.0465 mol), Pd (PPh3) 4 (1.1 g, 0.06 mol) was added to Intermediate 23-1 (7.0 g, 0.019 mol) 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol), 420 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 8.3 g (yield: 58%) of Compound 27.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.42 / S, 7.76 / D, 7.41 / M, 7.59 / D, 8.56 / D) 4H (8.30 / D, 7.71 / D, 7.51 / M, 8.28 / D, 7.22 / M)

LC / MS: m / z = 747 [(M + 1) ^< ^{+ &}

Example  28: Compound 28 Synthesis

Phenylboronic acid (10.6 g, 0.0465 mol), Pd (PPh3) 4 (1.1 g, 0.0465 mol) was added to Intermediate 23-1 (7.0 g, 0.019 mol) 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 340 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 6.8 g (yield: 62%) of Compound 28.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.33 / D, 7.59 / M, 8.00 / D, 7.98 / D, 7.50 / M, 7.52 / M, 8.45 / D, 7.76 / D, 7.42 / S )

LC / MS: m / z = 575 [(M + 1) ^< ^{+ &}

Example  29: Compound 29 Synthesis

Phenylboronic acid (12.9 g, 0.0465 mol), Pd (PPh3) 4 (1.1 g, 0.0465 mol) was added to Intermediate 23-1 (7.0 g, 0.019 mol) 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol), 220 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 7.3 g (yield: 57%) of Compound 29.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.48 / S, 7.76 / D) 4H (7.41 / M) 8H (8.28 / D, 7.51 / M)

LC / MS: m / z = 673 [(M + 1) ^< ^{+ &}

Example  30: Compound 30 Synthesis

(13.3 g, 0.0465 mol / sigma aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol), and potassium carbonate (7.9 g, 0.057 mol), 400 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 8.8 g (yield 67%) of Compound 30.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.42 / S, 7.76 / D, 7.45 / M, 8.30 / D, 8.21 / D, 8.13 / S, 8.55 / D, 7.25 / M, 7.33 / M , 7.94 / D) 4H (7.50 / D, 7.58 / M)

LC / MS: m / z = 693 [(M + 1) ^< ^{+ &}

Example  31: Compound 31 Synthesis

4-yl) phenylboronic acid (15.9 g, 0.0465 mol), Pd (PPh3) 4 (0.1 g, (1.1 g, 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 440 ml of THF and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 8.9 g (yield: 58%) of Compound 31.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.42 / S, 7.76 / D) 4H (8.30 / D, 7.71 / D, 7.41 / M) 8H (8.28 / D, 7.51 / M)

LC / MS: m / z = 801 [(M + 1) ^< ^{+ &}

Example  32: Compound 32 Synthesis

Pyrrolidin-2-ylboronic acid (13.4g, 0.0465mol), Pd (PPh3) 4 (1.1g, 0.001mol) was added to Intermediate 23-1 (7.0g, 0.019mol) 400 ml of THF was added to potassium carbonate (7.9 g, 0.057 mol), and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 7.9 g (yield: 60%) of Compound 32.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.76 / D, 8.38 / S, 7.94 / D, 7.33 / M, 7.25 / M, 8.55 / D, 8.12 / D, 7.29 / M, 7.50 / M , 7.63 / D, 7.64 / D, 7.57 / M, 9.30 / D)

LC / MS: m / z = 695 [(M + 1) ^< ^{+ &}

Example  33: Compound 33 Synthesis

3- (9-phenyl-9H-fluoren-9-yl) phenylboronic acid (16.8 g, 0.0465 mol), Pd (pph3) 4 (1.1 g, 0.001 mol) 220 ml of THF was added to potassium carbonate (7.9 g, 0.057 mol), and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 8.0 g (yield: 50%) of Compound 33.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.42 / S, 7.42 / M, 8.11 / D, 8.30 / D, 7.26 / M, 7.76 / D, 7.13 / D) 4H (7.87 / D, 7.38 / M, 7.28 / M, 7.55 / D, 7.11 / D, 7.33 / M)

LC / MS: m / z = 844 [(M + 1) ^< ^{+ &}

Example  34: Compound 34 Synthesis

(One) Manufacturing example  34-1: Synthesis of Intermediate 34-1

Dibenzo [b, d] thiophen-4-ylboronic acid (5.2 g, 0.0228 mol), Pd (PPh3) 4 (1.1 g, 0.001 mol), potassium carbonate (7.9 g, , 0.057 mol) was added 240 ml of THF, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 5.9 g (yield: 66%) of Intermediate 34-1.

LC / MS: m / z = 472 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  34-2: Compound 34 Synthesis

1-phenyl-1H-benzo [d] imidazol-2-ylboronic acid (3.4 g, 0.0144 mol), Pd (PPh3) 4 (0.7 g, 0.0006 mol), potassium (4.9 g, 0.036 mol), and the mixture was reacted at 65 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.1 g (yield: 58%) of Compound 34.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.42 / S, 8.31 / D, 7.61 / M, 8.47 / D, 8.45 / D, 7.52 / M, 7.50 / M, 7.98 / D, 7.54 / D 7.58 / M, 7.26 / M), 7.98 / D, 7.45 /

LC / MS: m / z = 585 [(M + 1) ^< ^{+ &}

Example  35: Compound 35 Synthesis

Yl) -1H-benzo [d] imidazol-2-ylboronic acid (18.8g, 0.0465mol / Sigma aldrich) was added to Intermediate 23-1 (7.0g, 0.019mol) , Pd (pph3) 4 (1.1 g, 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 500 ml of THF and reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 8.0 g (yield: 46%) of Compound 35.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.76 / D, 7.48 / S, 7.70 / S, 7.63 / D, 7.50 / M, 7.29 / M, 8.12 / D, 8.55 / D, 7.25 / M , 7.33 / M, 7.94 / D, 7.15 / D, 7.59 / D) 4H (7.50 / D, 7.58 /

LC / MS: m / z = 926 [(M + 1) ^< ^{+ &}

Example  36: Compound 36 Synthesis

4- (triphenylsilyl) phenylboronic acid (17.7 g, 0.0465 mol / sigma aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol), potassium carbonate (7.9 g, 0.057 mol), 480 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 8.8 g (yield: 53%) of Compound 36.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.42 / S, 7.76 / D) 4H (7.55 / M, 8.40 / D) 16H (7.46 / D, 7.37 / M)

LC / MS: m / z = 880 [(M + 1) ^< ^{+ &}

Example  37: Compound 37 Synthesis

2-phenyl-5H-pyrido [3,2-b] indol-5-ylboronic acid (13.4 g, 0.0465 mol / sigma aldrich), Pd (PPh3) 4 (1.1 g, 0.001 mol) and potassium carbonate (7.9 g, 0.057 mol) were added 400 ml of THF and reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 7.3 g (yield: 55%) of Compound 37.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.30 / S, 7.76 / D, 7.94 / D, 7.33 / M, 7.25 / M, 8.74 / D, 7.90 / D, 7.97 / D, 7.47 / M ) 4H (7.54 / M, 8.30 / D)

LC / MS: m / z = 695 [(M + 1) ^< ^{+ &}

Example  38: Compound 38 Synthesis

To the intermediate 23-1 (7.0 g, 0.019 mol) was added 9,9-diphenyl-9H-fluoren-2-ylboronic acid (16.8 g, 0.0465 mol), Pd (PPh3) 4 (1.1 g, 0.001 mol) 7.9 g, 0.057 mol), 460 ml of THF was added, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 10.0 g (yield: 62%) of Compound 38.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.42 / S, 7.76 / D, 8.14 / D, 7.96 / D, 7.87 / D, 7.38 / M, 7.28 / M, 8.28 / S, 7.55 / D ) 4H (7.26 / M) 8H (7.11 / D, 7.33 / M)

LC / MS: m / z = 844 [(M + 1) ^< ^{+ &}

Example  39: Compound 39 Synthesis

(One) Manufacturing example  39-1: Synthesis of Intermediate 39-1

3-bromo-4,7-phenanthroline (8.3 g, 0.032 mol / sigma Aldrich) is placed under 160 ml of hexane. Add TMEDA (24 ml, 0.16 mol) and n-BuLi (1.6 M, 100 ml, 0.16 mol) through the dropping funnel. After stirring for 3 hours under N ₂ , S ₂ Cl ₂ (6.4 ml, 0.08 mol) was slowly added and reacted at room temperature for 24 hours. The reaction mixture was cooled, layered under H ₂ O: methylene chloride (MC), and subjected to column purification (n-hexane: methylene chloride) to obtain 3.4 g (yield: 34%) of Intermediate 39-1.

LC / MS: m / z = 290 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  39-2: Compound 39 Synthesis

(Dibenzo [b, d] thiophen-4-yl) phenylboronic acid (4.0 g, 0.0132 mol), Pd (PPh3) 4 (0.6 g, 0.0006 mol) 140 ml of THF was added to potassium carbonate (4.5 g, 0.033 mol), and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 2.9 g (yield: 56%) of Compound 39.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.50 / M, 7.52 / M, 8.45 / D, 8.41 / D, 7.58 / M, 8.20 / D, 7.42 / S, 7.26 / D, 8.83 / D , 7.54 / D) 2H (8.81 / D, 7.28 / D, 7.98 / D)

LC / MS: m / z = 469 [(M + 1) ^< ^{+ &}

Example  40: Compound 40 Synthesis

4- (9,9-diphenyl-9H-fluoren-2-yl) phenylboronic acid (5.8 g, 0.0132 mol / sigma aldrich) and Pd (PPh3) 4 (0.6 g , 0.0006 mol) and potassium carbonate (4.5 g, 0.033 mol) were added 180 ml of THF, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.3 g (yield 65%) of Compound 40.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.63 / D, 7.93 / D, 7.87 / D, 7.38 / M, 7.28 / M, 7.55 / D, 7.42 / S, 7.26 / D, 8.83 / D , 7.54 / D, 7.98 / D, 7.77 / D) 2H (7.26 / M, 7.88 / D, 8.81 / D)

LC / MS: m / z = 603 [(M + 1) ^< ^{+ &}

Example  41: Compound 41 Synthesis

(One) Manufacturing example  41-1: Synthesis of Intermediate 41-1

800 ml of tetrachloride was added to 6-H-benzo [def] carbazole (5.0 g, 0.026 mol / sigma Aldrich) and bromine (18.3 g, 0.11 mol / sigma Aldrich) and stirred at room temperature for 1 hour. The reaction product was recrystallized to obtain 6.7 g (yield: 83%) of Intermediate 41-1.

LC / MS: m / z = 349 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  41-2: Intermediate 41-2 Synthesis

Pd (dba) 2 (0.6 g, 0.0007 mol / P & H TECH) and sodium tert-butoxide (2.7 g, 0.028 mol) were added to intermediate 41-1 (5.0 g, 0.014 mol) mol / Sigma Aldrich), and the mixture was reacted at 95 DEG C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.1 g (yield: 69%) of Intermediate 41-2.

LC / MS: m / z = 425 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  41-3: Compound 41 Synthesis

Pd (PPh3) 4 (0.6g, 0.0006mol / P & H TECH), potassium carbonate (3.0g, 0.022mol) were added to a solution of intermediate 41-2 (5.0g, 0.011mol) / sigma Aldrich), 100 ml of THF was added, and the mixture was reacted at 65 DEG C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (n-hexane: MC) to obtain 3.3 g (yield: 72%) of Compound 41.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m) 2H (8.34 / s, 8.10 / s, 7.71 / d, 7.58 / m, 7.50 / d, 7.41 / m) 4H (7.52 / d , 7.51 / m)

LC / MS: m / z = 420 [(M + 1) ^< ^{+ &}

Example  42: Compound 42 Synthesis

To a solution of Intermediate 41-2 (5.0 g, 0.011 mol) and 4- (2-phenyl-1H-benzo [d] imidazol-1-yl) phenylboronic acid (8.2 g, 0.026 mol / Synthesis was carried out in the same manner as used to give 42, 6.5 g (yield 73%) of the compound.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m) 2H (8.56 / d, 8.34 / d, 8.10 / s, 7.71 / m, 7.59 / d, 7.58 / m, 7.50 / d, 7.41 / m) 4H (8.28 / d, 7.79 / d, 7.68 / d, 7.51 / m, 7.22 /

LC / MS: m / z = 804 [(M + 1) ^< ^{+ &}

Example  43: Compound 43 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, with the intermediate 41-2 (5.0 g, 0.011 mol) and triphenylen-2-ylboronic acid (7.1 g, 0.026 mol / 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m) 2H (9.15 / s, 8.34 / s, 8.18 / d, 8.10 / s, 8.04 / d, 7.71 / m, 7.58 / m, 7.50 / d) 4H (8.93 / d, 8.12 / d, 7.88 / m, 7.82 / m)

LC / MS: m / z = 720 [(M + 1) ^< ^{+ &}

Example  44: Compound 44 Synthesis

(One) Manufacturing example  44-1: Synthesis of Intermediate 44-1

Synthesis was conducted in the same manner as in Production Example 41-3 using 3,5-dichlorophenylboronic acid (5.0 g, 0.026 mol / Chemosyntha) and phenyl boronic acid (7.1 g, 0.031 mol / TCI) (Yield: 71%).

LC / MS: m / z = 277 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  44-2: Compound 44 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, from the intermediate 41-2 (5.0 g, 0.011 mol) and the intermediate 44-1 (3.7 g, 0.013 mol) to obtain 5.44 g .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m) 2H (8.34 / s, 8.10 / s, 7.71 / d, 7.58 / m, 7.50 / d) 4H (7.41 / m) 8H (8.28 / d, 7.51 / m)

LC / MS: m / z = 730 [(M + 1) ^< ^{+ &}

Example  45: Compound 45 Synthesis

(One) Manufacturing example  45-1: Synthesis of Intermediate 45-1

4.5 g (yield 70%) of Intermediate 45-1 was obtained by the same method as in Production Example 41-2, except that 4-bromo-9H-carbazole (5.0 g, 0.020 mol) and bromobenzene (3.2 g, ≪ / RTI >

LC / MS: m / z = 322 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  45-2: Intermediate 45-2 Synthesis

Intermediate 45-1 (5 g, 0.016 mol) was dissolved in THF (100 ml), and 8 ml (0.001 mol) of 2M n-buLi was dropwise added thereto at -78 ° C. After stirring for 1 hour, trimethylborate (3 ml, 0.027 mol) was added and stirred at room temperature for 12 hours . After completion of the reaction, the reaction product was cooled, and the product was separated into H + 0: MC and column-purified (n-hexane: MC) to obtain 2.3 g (yield: 51%) of Intermediate 45-2.

LC / MS: m / z = 287 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  45-3: Compound 45 Synthesis

Intermediate 41-2 (5.0 g, 0.011 mol) and Intermediate 45-2 (3.3 g, 0.013 mol) were added to the residue to obtain 45 (5.8 g, yield 70%) of the compound 45 .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.55 / d, 8.34 / s, 8.10 / s, 7.94 / d, 7.79 / d, 7.71 / d, 7.59 / d, 7.43 / m, 7.33 / m , 7.25 / m) 3H (7.45 / m) 6H (7.58 / m, 7.50 / d)

LC / MS: m / z = 750 [(M + 1) ^< ^{+ &}

Example  46: Compound 46 Synthesis

(One) Manufacturing example  46-1: Synthesis of Intermediate 46-1

1100 ml of tetrachloride was added to 6-benzo [def] carbazole (5.0 g, 0.026 mol) and bromine (36.6 g, 0.22 mol) and the mixture was stirred at room temperature for 1 hour. The reaction product was recrystallized to obtain 10.5 g (yield: 80%) of Intermediate 46-1.

LC / MS: m / z = 506 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  46-2: Intermediate 46-2 Synthesis

Intermediate 46-1 (5.0 g, 0.010 mol) and bromobenzene (1.6 g, 0.011 mol) were added and the compound was synthesized by the same method as in Production Example 41-2 to give 4.3 g (yield 67%) of Compound 46-2.

LC / MS: m / z = 583 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  46-3: Compound 46 Synthesis

The compound 46 (5.9 g, yield 70%) was synthesized by the same method as in Production Example 41-2 except that Intermediate 46-2 (5.0 g, 0.009 mol) and 9H-carbazole (5.7 g, 0.034 mol / .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m) 2H (7.80 / s, 7.70 / d, 7.58 / m) 4H (8.55 / d, 8.12 / d, 7.94 / d, 7.63 / d , 7.33 / m, 7.29 / m, 7.25 / m) 6H (7.50 / m)

LC / MS: m / z = 929 [(M + 1) ^< ^{+ &}

Example  47: Compound 47 Synthesis

(One) Manufacturing example  47-1: Intermediate 47-1 Synthesis

4-ylboronic acid (3.0 g, 0.013 mol / TCI) was added to a solution of Intermediate 41-2 (5.0 g, 0.011 mol) and dibenzo [b, d] thiophen- -1, 4.3 g (yield: 74%). (M / z = 529)

LC / MS: m / z = 529 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  47-2: Compound 47 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, except that Intermediate 47-1 (5.0 g, 0.010 mol) and triphenylen-2-ylboronic acid (3.3 g, 0.012 mol) ≪ / RTI >

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.45 / d, 8.41 / d, 8.20 / d, 8.18 / d, 8.04 / d, 7.98 / d, 7.52 / m, 7.45 / m (7.58 / m, 7.50 / d)) 2H (8.93 / d, 8.34 / s, 8.12 / d, 8.10 / s, 7.88 /

LC / MS: m / z = 676 [(M + 1) ^< ^{+ &}

Example  48: Compound 48 Synthesis

(One) Manufacturing example  48-1: Synthesis of Intermediate 48-1

 Intermediate 48-1 (4.5 g, 71%) was synthesized in the same manner as in Production Example 41-3, except that Intermediate 41-2 (5.0 g, 0.011 mol) and Intermediate 44-1 (3.7 g, 0.013 mol) ≪ / RTI >

LC / MS: m / z = 578 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  48-2: Intermediate 48-2 Synthesis

(5.0 g, 0.016 mol / matrix scientific) and 9H-carbazole (2.7 g, 0.016 mol) were added to a solution of (Yield: 73%) of Intermediate 48-2.

LC / MS: m / z = 403 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  48-3: Compound 48 Synthesis

Intermediate 48-1 (5.0 g, 0.009 mol) and Intermediate 48-2 (4.4 g, 0.011 mol) were added and the compound 48 was synthesized in the same manner as in Production Example 41-3 to give 5.6 g (yield 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.12 / d, 7.94 / d, 7.70 / s, 7.63 / d, 7.59 / d, 7.50 / m, 7.33 / m, 7.29 / m M, 7.55 / d) 2H (8.34 / s, 8.10 / s, 7.71 / d, 7.45 / m, 7.41 /

LC / MS: m / z = 856 [(M + 1) ^< ^{+ &}

Example  49: Compound 49 Synthesis

(One) Manufacturing example  49-1: Synthesis of intermediate 49-1

Tetrachloride (400 ml) was added to 6-benzo [def] carbazole (5.0 g, 0.026 mol) and bromine (9.2 g, 0.06 mol) and the mixture was stirred at room temperature for 1 hour. The reaction product was recrystallized to obtain 5.4 g (yield: 77%) of Intermediate 49-1.

LC / MS: m / z = 270 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  49-2: Intermediate 49-2 Synthesis

Intermediate 49-1 (5.0 g, 0.019 mol) and bromobenzene (15.9 g, 0.0465 mol) were added and the reaction mixture was reacted in the same manner as in Production Example 41-2 to give intermediate 49-2 (yield: 71%).

LC / MS: m / z = 346 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  49-3: Compound 49 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, from Intermediate 49-2 (5.0 g, 0.014 mol) and Intermediate 44-1 (4.7 g, 0.017 mol) to obtain Compound 49 (5.7 g, 71% .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / s, 7.45 / m) 2H (8.12 / d, 7.88 / d, 7.85 / d, 7.82 / m, 7.58 / m, 7.50 / d, 7.41 / m, 7.25 / d) 4H (8.28 / d, 7.51 / m)

LC / MS: m / z = 575 [(M + 1) ^< ^{+ &}

Example  50: Compound 50 Synthesis

(One) Manufacturing example  50-1: Synthesis of Intermediate 50-1

2-ylboronic acid (5.0 g, 0.018 mol) and 4- (triphenylen-2-yl) phenylboronic acid (4.2 g, 0.021 mol) 1, 4.5 g (yield: 72%).

LC / MS: m / z = 348 [(M + 1) ^< ^{+ &}

(One) Manufacturing example  50-2: Compound 50 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, with the intermediate 49-2 (5.0 g, 0.014 mol) and Intermediate 50-1 (5.9 g, 0.017 mol) added thereto to obtain 5.7 g (yield 72% .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.93 / s, 7.45 / m) 2H (8.93 / d, 7.58 / m, 7.50 / d) 4H (8.12 / d, 7.88 / d, 7.82 / m, 7.25 / d)

LC / MS: m / z = 570 [(M + 1) ^< ^{+ &}

Example  51: Compound 57 Synthesis

(One) Manufacturing example  51-1: Intermediate 57-1 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, with the intermediate 49-2 (5.0 g, 0.014 mol) and 4-bromophenylboronic acid (3.4 g, 0.017 mol / TCI) %).

LC / MS: m / z = 422 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  51-2: Compound 57 Synthesis

(4.3 g, 0.012 mol / matrix science) was added to a solution of Intermediate 57-1 (5.0 g, 0.012 mol) and N- (biphenyl-4-yl) -9,9- -2, the compound 57 (5.7 g, yield 67%) was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / s, 7.87 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.41 / m, 7.38 / m, 7.28 / m, 6.75 / s 7.58 d) 2H (8.12 / d, 7.88 / d, 7.82 / m, 7.58 / m, 7.52 / d, 7.51 / m, 7.50 / d, 1.72 / s)

LC / MS: m / z = 703 [(M + 1) ^< ^{+ &}

Example  52: Compound 58 Synthesis

(5.0 g, 0.012 mol) and N- (biphenyl-4-yl) -9,9-dimethyl-7-phenyl-9H-fluoren-2-amine (5.3 g, 0.012 mol / 2daybiochem) Synthesis was conducted in the same manner as in Production Example 41-2 to give compound 58 (6.8 g, yield 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / s, 7.93 / d, 7.77 / s, 7.63 / d, 7.62 / d, 7.45 / m, 6.75 / s, 6.58 / d) 2H (8.12 7.58 / d, 7.51 / m, 6.69 / d), 7.48 / d, 7.88 / d, 7.82 /

LC / MS: m / z = 779 [(M + 1) ^< ^{+ &}

Example  53: Compound 59 Synthesis

(One) Manufacturing example  53-1: Synthesis of intermediate 59-1

9,9-dimethyl-9H-fluoren-2-amine (5.0g, 0.024mol / 2daybiochem) and 9,9-dimethyl-9H- -2, 5.7 g (71%) of the intermediate 59-1 was obtained.

LC / MS: m / z = 324 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  53-2: Intermediate 59-2 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-2, except that Intermediate 55-1 (5.0 g, 0.012 mol) and Intermediate 59-1 (3.9 g, 0.012 mol) were added and the intermediate 59-2 and 5.7 g (71% ≪ / RTI >

LC / MS: m / z = 665 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  53-3: Compound 59 Synthesis

The compound 59 (4.6 g, Yield: 72%) was synthesized in the same manner as in Production Example 41-2, except that Intermediate 59-2 (5.0 g, 0.008 mol) and 4-bromobiphenyl (1.9 g, 0.011 mol / ≪ / RTI >

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.94 / d, 7.93 / d, 7.87 / d, 7.60 / s, 7.55 / d, 7.50 / d, 7.45 / m, 7.41 / m, 7.38 / m D, 7.88 / d, 7.82 / d, 7.62 / d, 7.62 / d, 7.58 / m, 7.54 / d , 7.52 / d, 7.51 / m, 7.50 / d, 6.69 / d, 1.72 / s)

LC / MS: m / z = 805 [(M + 1) ^< ^{+ &}

Example  54: Compound 60 Synthesis

(One) Manufacturing example  54-1: Synthesis of intermediate 60-1

9,9-dimethyl-9H-fluorene (5.0g, 0.016mol / 2day biochem), 4- (9,9-dimethyl-9H- fluoren- 2- yl) aniline (4.6g, 0.016 mol / 2day biochem) was added thereto to obtain Intermediate 60-1, 5.6 g (yield: 63%) by the same method as in Production Example 41-2.

LC / MS: m / z = 553 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  54-2: Compound 60 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-2, except that Intermediate 55-1 (5.0 g, 0.012 mol) and Intermediate 60-1 (6.6 g, 0.012 mol) were added to obtain Compound 60 (7.5 g, yield 70% .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / d, 7.45 / m) 2H (8.12 / d, 7.93 / d, 7.88 / d, 7.87 / d, 7.82 / m, 7.77 / s, 7.63 7.58 / d, 7.50 / d, 7.38 / 7.28 / m) 4H (1.72 / s) 6H (7.54 / d, 6.69 / d)

LC / MS: m / z = 896 [(M + 1) ^< ^{+ &}

Example  55: Compound 51 Synthesis

(One) Manufacturing example  55-1: Synthesis of Intermediate 51-1

Synthesis was conducted in the same manner as in Production Example 41-2, except that Intermediate 55-1 (5.0 g, 0.012 mol) and 3,6-dibromo-9H-carbazole (3.9 g, 0.012 mol / , 5.4 g (yield: 68%).

LC / MS: m / z = 666 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  55-2: Compound 51 Synthesis

The compound 51 (5.0 g, 0.008 mol) and 9H-carbazole (2.6 g, 0.016 mol) were added to the reaction mixture to obtain the compound 51 (5.0 g, yield 75%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / s, 7.63 / d, 7.62 / d, 7.45 / m, 7.31 / d) 2H (8.55 / d, 7.88 / d, 7.82 / m, 7.79 7.50 / d, 7.50 / d, 7.50 / m, 7.33 / m, 7.29 / m, 7.25 / )

LC / MS: m / z = 839 [(M + 1) ^< ^{+ &}

Example  56: Compound 52 Synthesis

(One) Manufacturing example  56-1: Synthesis of Intermediate 52-1

Synthesis was conducted in the same manner as in Production Example 41-2 except that Intermediate 55-1 (5.0 g, 0.012 mol) and 3-bromo-9H-carbazole (3.0 g, 0.011 mol / g (yield: 76%).

LC / MS: m / z = 587 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  56-2: Compound 52 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-2, except that Intermediate 52-1 (5.0 g, 0.009 mol) and 2-phenyl-1H-benzo [d] imidazole (1.7 g, 0.009 mol / , 4.7 g (75% yield).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.56 / d, 8.55 / d, 7.94 / d, 7.93 / d, 7.63 / d, 7.59 / d, 7.50 / s, 7.45 / m, 7.41 / m M, 7.31 / d, 7.25 / m) 2H (8.28 d, 8.12 d, 7.88 d, 7.82 m, 7.79 d, 7.68 d, 7.58 m, 7.51 m, , 7.22 / m)

LC / MS: m / z = 701 [(M + 1) ^< ^{+ &}

Example  57: Compound 54 Synthesis

(One) Manufacturing example  57-1: Synthesis of Intermediate 54-1

3-ylboronic acid (5.0 g, 0.024 mol / TCI) and 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 0.017 mol / 2, 7.3 g (yield 70%) of Intermediate 54-1 was obtained.

LC / MS: m / z = 442 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  57-2: Compound 54 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, with the intermediate 49-2 (5.0 g, 0.014 mol) and Intermediate 54-1 (7.5 g, 0.017 mol) added thereto to obtain 6.25 g (74% .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.93 / s, 7.87 / d, 7.77 / s, 7.69 / d, 7.45 / m, 7.33 / m, 7.25 / m 7.58 / d, 7.88 / d, 7.8 / m, 7.58 /

LC / MS: m / z = 664 [(M + 1) ^< ^{+ &}

Example  58: Compound 55 Synthesis

(One) Manufacturing example  58-1: Intermediate 55-1 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, except that Intermediate 49-2 (5.0 g, 0.014 mol) and 3,5-dibromophenylboronic acid (4.8 g, 0.017 mol / sigma aldrich) (Yield: 74%).

LC / MS: m / z = 521 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  58-2: Compound 55 Synthesis

Compound 55 (5.3 g, 0.010 mol) was synthesized by the same method as in Production Example 41-2, except that Intermediate 55-1 (5.0 g, 0.010 mol) and 2-phenyl-1H-benzo [d] imidazole (Yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / d, 7.45 / m, 7.2 / s) 2H (8.56 / d, 8.12 / d, 8.09 / d, 7.88 / d, 7.82 / m, 7.59 7.58 / d, 7.41 / m) 4H (8.28 / d, 7.51 / m, 7.22 /

LC / MS: m / z = 728 [(M + 1) ^< ^{+ &}

Example  59: Compound 56 Synthesis

(One) Manufacturing example  59-1: Intermediate 56-1 Synthesis

(3.3 g, 0.012 mol / ark pharm) was added to a solution of the intermediate 55-1 (5.0 g, 0.012 mol) and 5-bromo-2-phenyl-1H- To obtain 5.2 g (yield 70%) of Intermediate 56-1.

LC / MS: m / z = 614 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  59-2: Compound 56 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-2 except that Intermediate 56-1 (5.0 g, 0.008 mol) and 2-phenyl-1H-benzo [d] imidazole (1.5 g, 0.010 mol) (Yield 69%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.56 / d, 7.93 / s, 7.70 / s, 7.45 / m, 7.15 / d) 2H (8.12 / d, 7.88 / d, 7.82 / m, 7.79 7.58 / d, 7.58 / d, 7.50 / d, 7.41 / m, 7.22 /

LC / MS: m / z = 728 [(M + 1) ^< ^{+ &}

Example  60: Compound 53 Synthesis

(One) Manufacturing example  60-1: Intermediate 53- 1 synthesis

Synthesis was conducted in the same manner as in Production Example 41-2 except that Intermediate 49-1 (5.0 g, 0.019 mol) and 4-bromodibenzo [b, d] thiophene (5.0 g, 0.019 mol) (Yield: 71%).

LC / MS: m / z = 452 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  60-2: Compound 53 Synthesis

(Yield: 74%) was obtained by the same method as in Production Example 41-3, with the intermediate 53-1 (5.0 g, 0.011 mol) and triphenylen-2-ylboronic acid (3.6 g, ≪ / RTI >

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.98 / d, 7.93 / s, 7.50 / m, 7.3 / d) 2H (8.93 / d, 8.45 / d, 7.52 / m) 4H (8.12 / d, 7.88 / d, 7.82 / m)

LC / MS: m / z = 600 [(M + 1) ^< ^{+ &}

Example  61: Compound 61 Synthesis

(One) Manufacturing example  61-1: Synthesis of intermediate 61-1

800 ml of tetrachloride was added to phenanthro [4,5-bcd] furan (5.0 g, 0.026 mol / TCI) and bromine (18.3 g, 0.11 mol) and stirred at room temperature for 1 hour. The reaction product was recrystallized to obtain Intermediate 61-1 (7.4 g, yield: 81%).

LC / MS: m / z = 350 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  61-2: Compound 61 Synthesis

The compound 61 (2.7 g, yield 70%) was synthesized by the same method as in Production Example 41-3, with the intermediate 61-1 (5.0 g, 0.011 mol) and phenyl boronic acid (7.1 g, 0.026 mol / ≪ / RTI >

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.34 / s, 8.10 / s, 7.71 / m, 7.41 / m) 4H (7.52 / d, 7.51 / m)

LC / MS: m / z = 345 [(M + 1) ^< ^{+ &}

Example  62: Compound 62 Synthesis

Synthesis was conducted according to the same method as in Production Example 41-3, from Intermediate 61-1 (5.0 g, 0.011 mol) and Intermediate 44-1 (7.4 g, 0.026 mol) to obtain 62 (5.3 g, 74% .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.34 / s, 8.10 / s, 7.71 / d) 4H (7.41 / m) 8H (8.28 / d, 7.51 / m)

LC / MS: m / z = 655 [(M + 1) ^< ^{+ &}

Example  63: Compound 63 Synthesis

(One) Manufacturing example  63-1: Synthesis of intermediate 63-1

phenanthro [4,5-bcd] furan (5.0 g, 0.026 mol) and bromine (36.6 g, 0.22 mol) were added 1100 ml of tetrachloride and stirred at room temperature for 1 hour. The reaction product was recrystallized to obtain 10.9 g (83% yield) of Intermediate 63-1.

LC / MS: m / z = 507 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  63-2: Compound 63 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, with the intermediate 63-1 (5.0 g, 0.011 mol) and triphenylen-2-ylboronic acid (14.2 g, 0.052 mol / 75%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.26 / s, 7.71 / d) 4H (8.45 / d, 8.41 / d, 8.20 / d, 7.98 / d, 7.58 / m, 7.52 / m, 7.50 / m)

LC / MS: m / z = 601 [(M + 1) ^< ^{+ &}

Example  64: Compound 64 Synthesis

(One) Manufacturing example  64-1: Synthesis of intermediate 64-1

Synthesis was conducted in the same manner as in Production Example 41-3, with the intermediate 61-1 (5.0 g, 0.011 mol) and dibenzo [b, d] thiophen-4-ylboronic acid (3.0 g, 0.013 mol) , 3.7 g (yield: 74%).

LC / MS: m / z = 454 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  64-2: Compound 64 Synthesis

Synthesis was conducted in the same manner as in Production Example 41-3, with the intermediate 64-1 (5.0 g, 0.011 mol) and triphenylen-2-ylboronic acid (3.6 g, 0.013 mol / 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.26 / s, 7.71 / d) 4H (8.45 / d, 8.41 / d, 8.20 / d, 7.98 / d, 7.58 / m, 7.52 / m, 7.50 / m)

LC / MS: m / z = 922 [(M + 1) ^< ^{+ &}

Example  65: Compound 68 Synthesis

(One) Manufacturing example  65-1: Synthesis of Intermediate 68-1

phenanthro [4,5-bcd] furan (5.0 g, 0.026 mol) and bromine (9.2 g, 0.06 mol) were added 400 ml of tetrachloride and stirred at room temperature for 1 hour. The reaction product was recrystallized to obtain 5.4 g (yield: 77%) of Intermediate 68-1.

LC / MS: m / z = 271 [(M + 1) ^< ^{+ &}

(2) Manufacturing example  65-2: Intermediate 68-2 Synthesis

(Yield: 74%) was obtained by the same method as in Production Example 41-3, except that Intermediate 68-1 (5.0 g, 0.018 mol) and 4-bromophenylboronic acid (3.5 g, ≪ / RTI >

LC / MS: m / z = 347 [(M + 1) ^< ^{+ &}

(3) Manufacturing example  65-3: Compound 68 Synthesis

4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.1 g, 0.014 mol) was added to a solution of Intermediate 68-2 (5.0 g, 0.014 mol) Synthesis was carried out in the same manner as used to obtain 68, 5.0 g (yield 68%) of compound 68.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / s, 7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.38 / m, 7.28 / m, 6.75 / s, 6.58 / d ) 2H (8.12 / d, 7.88 / d, 7.82 / m, 7.52 / d, 7.51 /

LC / MS: m / z; 628 < RTI ID = 0.0 > [(M + 1) ⁺ ]

Example  66: Compound 69 Synthesis

(5.0 g, 0.014 mol) and bis (9,9-dimethyl-7-phenyl-9H-fluoren-2-yl) amine (7.8 g, 0.014 mol) Synthesis was conducted in the same manner as above to obtain Compound 69 (7.7 g, yield 67%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.93 / s) 2H (8.12 / d, 7.93 / d, 7.88 / d, 7.82 / m, 7.77 / s, 7.63 / d, 7.62 / d, 7.54 (7.52 / d, 7.51 / m, 1.72 / s)

LC / MS: m / z = 821 [(M + 1) ^< ^{+ &}

Abbreviations used in the embodiment of the present invention are as follows.

NPB: N, N'-bis (naphthalen-1-yl) -N,

Ir (ppy) ₃ : Iridium, tris (2-phenylpyidine)

Balq: Bis (2-methyl-8-quinolinolato-N1, O8) - (1,1'-Biphenyl-4-olato) aluminum

Alq ₃ : tris (8-quinolinolato) -aluminium (III)

CBP: (4,4-N, N-dicarbazole) biphenyl

Device Example  1: Compound 1 The light-  As a host material Organic electroluminescent device  Produce

Depositing NPB on the glass substrate coated with ITO to form a hole transport layer was of 120nm, followed by Ir (ppy) the deposition rate of the compounds 1 to ₃ as the dopant 0.1nm / sec, Ir (ppy) ₃ deposition rate 0.009nm / sec, and Ir (ppy) ₃ was doped so that the deposition rate ratio was 9% to form a light emitting layer with a thickness of 30 nm on the hole transport layer.

Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and Alq3 was deposited thereon to form an electron transporting layer of 40 nm, and lithium fluoride was deposited thereon Thereby forming an electron injection layer having a thickness of 1 nm. Aluminum was deposited on the electron injecting layer to form a 120 nm cathode, thereby fabricating an organic electroluminescent device.

At this time, the deposition rate of each material was set to 0.1 nm / sec for compound 1, NPB, Alq ₃ , Balq, 0.01 nm / sec for lithium fluoride, and 0.5 nm / sec for aluminum.

Device Example  2 to 66

Organic electroluminescent devices of Device Examples 2 to 66 were fabricated in the same manner as in the device example 1, except that the luminescent material described in the following Table 1 was used in place of the compound 2.

Device comparison example  One

An organic electroluminescent device of Comparative Example 1 was manufactured in the same manner as in Example 1 except that (4,4-N, N-dicarbazole) biphenyl (CBP)

Table 1 shows the results of comparing the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 66 and the device comparison example 1.

division Emitting material The driving voltage (V)
(at 1000 cd / m ² ) Luminous efficiency
(cd / A) Color coordinates
CIE_ (x, y) Device Embodiment 1 Compound 1 4.5 28 0.31, 0.62 Device Example 2 Compound 2 5.5 22 0.30, 0.60 Device Embodiment 3 Compound 3 5.0 24 0.32, 0.65 Device Example 4 Compound 4 5.1 24 0.33, 0.60 Element Embodiment 5 Compound 5 5.3 24 0.33, 0.61 Device Example 6 Compound 6 5.6 21 0.32, 0.63 Device Example 7 Compound 7 5.1 23 0.33, 0.62 Device Example 8 Compound 8 5.5 22 0.30, 0.64 Device Example 9 Compound 9 5.6 21 0.30, 0.66 Element Embodiment 10 Compound 10 5.1 24 0.33, 0.63 Element Embodiment 11 Compound 11 5.0 24 0.32, 0.62 Device Example 12 Compound 12 4.9 24 0.31, 0.63 Device Embodiment 13 Compound 13 4.5 28 0.32, 0.62 Device Embodiment 14 Compound 14 4.3 29 0.32, 0.65 Device Example 15 Compound 15 4.5 29 0.33, 0.60 Device Embodiment 16 Compound 16 4.8 25 0.33, 0.61 Device Example 17 Compound 17 5.0 24 0.32, 0.63 Element Embodiment 18 Compound 18 5.0 24 0.33, 0.63 Element Embodiment 19 Compound 19 5.1 24 0.32, 0.63 Device Embodiment 20 Compound 20 5.6 22 0.33, 0.62 Device Example 21 Compound 21 4.1 40 0.30, 0.64 Device Embodiment 22 Compound 22 4.1 31 0.30, 0.66 Device Example 23 Compound 23 4.2 30 0.33, 0.63 Device Embodiment 24 Compound 24 4.0 30 0.32, 0.62 Device Example 25 Compound 25 4.8 24 0.30, 0.64 Device Embodiment 26 Compound 26 4.2 30 0.30, 0.66 Device Example 27 Compound 27 4.1 49 0.33, 0.62 Device Example 28 Compound 28 4.0 30 0.30, 0.64 Element Embodiment 29 Compound 29 3.8 28 0.30, 0.66 Device Example 30 Compound 30 4.8 25 0.30, 0.66 Element Embodiment 31 Compound 31 4.3 29 0.33, 0.63 Device Example 32 Compound 32 4.5 30 0.33, 0.62 Device Example 33 Compound 33 4.8 25 0.33, 0.62 Device Example 34 Compound 34 4.8 25 0.30, 0.64 Device Example 35 Compound 35 4.3 29 0.30, 0.66 Device Example 36 Compound 36 4.8 26 0.30, 0.64 Device Example 37 Compound 37 4.2 39 0.30, 0.64 Device Example 38 Compound 38 4.9 24 0.30, 0.66 Device Example 39 Compound 39 5.1 24 0.33, 0.62 Device Example 40 Compound 40 5.2 23 0.30, 0.64 Device Example 41 Compound 41 5.3 31 0.33, 0.64 Device Example 42 Compound 42 4.6 43 0.30, 0.63 Device Embodiment 43 Compound 43 5.2 32 0.31, 0.62 Element Embodiment 44 Compound 44 4.5 40 0.32, 0.62 Device Example 45 Compound 45 5.1 31 0.34, 0.63 Device Embodiment 46 Compound 46 5.1 30 0.33, 0.63 Device Embodiment 47 Compound 47 5.4 28 0.31, 0.64 Device Example 48 Compound 48 5.7 29 0.30, 0.63 Device Example 49 Compound 49 4.6 45 0.32, 0.61 Device Example 50 Compound 50 5.5 31 0.33, 0.61 Device Embodiment 51 Compound 57 5.1 31 0.33, 0.64 Device Example 52 Compound 58 5.5 31 0.32, 0.64 Element Embodiment 53 Compound 59 5.2 32 0.31, 0.63 Device Example 54 Compound 60 5.1 32 0.33, 0.63 Device Example 55 Compound 51 5.3 33 0.33, 0.62 Device Example 56 Compound 52 5.5 29 0.31, 0.62 Device Example 57 Compound 54 5.4 28 0.31, 0.62 Element Embodiment 58 Compound 55 5.5 29 0.34, 0.63 Device Example 59 Compound 56 5.5 31 0.31, 0.63 Device Example 60 Compound 53 5.6 33 0.33, 0.61 Element Embodiment 61 Compound 61 6.0 27 0.33, 0.63 Device Embodiment 62 Compound 62 6.1 26 0.31, 0.64 Device Example 63 Compound 63 5.9 28 0.32, 0.62 Device Example 64 Compound 64 5.6 29 0.32, 0.63 Device Example 65 Compound 68 5.7 26 0.31, 0.61 Element Embodiment 66 Compound 69 5.9 26 0.32, 0.62 Device Comparative Example 1 CBP 6.5 19 0.30, 0.63

Measurement of driving voltage and luminous efficiency

The organic light emitting element made from above (substrate size: 25 * 25mm ² / deposition area: ² * 2mm 2) an IVL measuring set (CS-2000 + fixture + IVL program) by the current deposition raises by 1mA / m ² and then fixed to the the brightness of light emitted by the surface (cd / m ^2), a driving voltage (V), current density (a / m ^2), luminous efficiency (cd / a) drive voltage when measured brightness is 1000cd / m ² days and luminous efficiency Shown in Table 1 above.

According to Table 1, when the compound for an organic electroluminescence device according to the present invention is used as a host material of a light emitting layer of an organic electroluminescence device, the driving voltage is considerably lower than that of the conventional CBP as a light emitting material and the luminous efficiency is considerably improved Able to know.

Claims (14)

A compound for an organic electroluminescence device represented by Structural Formula (1) below.
[Structural formula 1]

In the above formula 1,
X ¹ represents an oxygen atom, a sulfur atom,

,

,

, or

ego,
Ar ¹ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
R ⁷ to R ¹¹ may be the same or different from each other, and R ⁷ to R ¹¹ each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
Y ¹ And Y ² may be the same or different from each other, and Y ¹ And Y < ² > are each independently a nitrogen atom, or

ego,
R ¹² represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ¹ to R ⁶ may be the same or different from each other and each of R ¹ to R ⁶ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. The method according to claim 1,
The organic electroluminescent device compound is represented by any one of the following structural formulas 2 to 4,

In the above Structural Formulas 2 to 4,
Ar ¹ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
Y ¹ And Y ² may be the same or different from each other, and Y ¹ And Y < ² > are each independently a nitrogen atom, or

ego,
R ¹² represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ¹ to R ⁶ may be the same or different from each other and each of R ¹ to R ⁶ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. 3. The method of claim 2,
R ¹ to R ⁴ , and R ¹² may be the same or different from each other, and R ¹ to R ⁴ and R ¹² are each independently a hydrogen atom,

,

,

,

,

,

,

,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,
X ² to X ⁹ may be the same or different from each other, and each of X ² to X ⁹ independently represents an oxygen atom, a sulfur atom,

, or

ego,
Ar ² represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
R ⁵⁷ and R ⁵⁸ may be the same or different from each other, and R ⁵⁷ and R ⁵⁸ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
Y ³ To Y ¹⁶ may be the same or different from each other, and Y ³ To Y ¹⁶ each independently represents a nitrogen atom, or

ego,
R ⁵⁹ represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ¹³ to R ⁵⁶ may be the same or different from each other, and each of R ¹³ to R ⁵⁶ independently represents a hydrogen atom, a silyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, Or an unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. The method of claim 3,
R ¹³ to R ⁵⁶ may be the same or different from each other, and R ¹³ to R ⁵⁶ each independently represent a hydrogen atom,

,

,

,

,

,

,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,
Ar ³ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
X ¹⁰ to X ¹⁴ may be the same or different from each other, and X ¹⁰ to X ¹⁴ each independently represent an oxygen atom, a sulfur atom,

, or

ego,
Ar ⁴ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
R ¹⁰⁵ and R ¹⁰⁶ may be the same or different from each other, and each of R ¹⁰⁵ and R ¹⁰⁶ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
Y ¹⁷ And Y ¹⁸ may be the same or different from each other, and Y ¹⁷ And Y ¹⁸ are each independently a carbon atom or a silicon atom,
Y ¹⁹ to Y ²³ may be the same or different from each other, Y ¹⁹ to Y ²³ each independently represent a nitrogen atom, or

ego,
R ¹⁰⁷ represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ⁶⁰ to R ¹⁰⁴ may be the same or different from each other, and each of R ⁶⁰ to R ¹⁰⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. 3. The method of claim 2,
Ar ¹ is

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,
X ¹⁵ represents an oxygen atom, a sulfur atom,

, or

ego,
Ar ⁵ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
R ¹¹³ and R ¹¹⁴ may be the same or different from each other, and each of R ¹¹³ and R ¹¹⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ¹⁰⁸ to R ¹¹² may be the same or different from each other, and each of R ¹⁰⁸ to R ¹¹² independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. 3. The method of claim 2,
R ⁵ and R ⁶ may be the same or different from each other, and R ⁵ and R ⁶ are each independently a hydrogen atom,

,

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,
Ar ⁶ and Ar ⁷ may be the same or different from each other, Ar ⁶ and Ar ⁷ each independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
X ¹⁶ represents an oxygen atom, a sulfur atom,

, or

ego,
Ar ⁸ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
R ¹⁴¹ and R ¹⁴² may be the same or different from each other, and R ¹⁴¹ and R ¹⁴² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ¹¹⁵ to R ¹⁴⁰ may be the same or different from each other, and each of R ¹¹⁵ to R ¹⁴⁰ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. The method according to claim 6,
Ar ⁶ and Ar ⁷ may be the same or different from each other, Ar ⁶ and Ar ⁷ are each independently

,

,

,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,
Ar ⁹ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
X ¹⁷ and X ¹⁸ may be the same or different from each other, and X ¹⁷ and X ¹⁸ are each independently an oxygen atom, a sulfur atom,

, or

ego,
Ar ¹⁰ represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, An unsubstituted C1 to C30 heteroaryl group,
R ¹⁶¹ and R ¹⁶² may be the same or different from each other, and R ¹⁶¹ and R ¹⁶² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
Y ²⁴ To Y ²⁶ may be the same or different from each other, and Y ²⁴ To Y < ²⁶ > each independently represent a nitrogen atom, or

ego,
R ¹⁶³ represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ¹⁴³ to R ¹⁶⁰ may be the same or different from each other, and each of R ¹⁴³ to R ¹⁶⁰ independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. The method according to claim 6,
R ¹¹⁵ to R ¹⁴⁰ may be the same or different from each other, and R ¹¹⁵ to R ¹⁴⁰ each independently represent a hydrogen atom,

,

,

, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted or unsubstituted C1 to C30 heterocycloalkyl group,
Y ²⁷ To Y ²⁹ may be the same or different from each other, and Y ²⁷ To Y ²⁹ each independently represent a nitrogen atom, or

ego,
R ¹⁷³ represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C1 to C30 heteroaryl group,
R ¹⁶⁴ to R ¹⁷² may be the same or different from each other and each of R ¹⁶⁴ to R ¹⁷² independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, A substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. The method according to claim 1,
Wherein the compound for an organic electroluminescence device is any one selected from compounds 1 to 441 represented by the following formulas.

An organic electroluminescent device comprising the compound for an organic electroluminescent device according to any one of claims 1 to 9. 1. An organic electroluminescent device comprising a first electrode, a second electrode, and a single or a plurality of organic layers between the first electrode and the second electrode,
Wherein at least one organic layer selected from the single or plural organic layers includes the organic electroluminescence compound according to any one of claims 1 to 9. 12. The method of claim 11,
Wherein the single or plural organic layers include a light emitting layer. 12. The method of claim 11,
Wherein the plurality of organic layers include a light emitting layer and the plurality of organic layers further include at least one selected from an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, a hole transporting layer and a hole injecting layer Organic electroluminescent device. 13. The method of claim 12,
Wherein the light emitting layer comprises a host and a dopant.

Images