KR20170065291A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the same. More specifically, the present invention relates to a novel compound having a hole injecting ability, a light emitting ability, an electron injecting ability, , A high luminous efficiency, a low driving voltage, a long lifetime, and the like.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel compound having excellent hole injecting and transporting ability, electron injecting ability, To an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and life span.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as "organic EL devices") led to blue electroluminescence using anthracene single crystals in 1965 based on observation of organic thin film luminosity of Bernanose in the 1950s, (Tang) and a functional layer of a light emitting layer. Since then, in order to make a high efficiency and high number of organic EL devices, each organic EL element has been developed into a form of introducing a characteristic organic material layer in the EL device, leading to the development of a specialized material used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

The light emitting layer forming material of the organic EL device can be classified into blue, green and red light emitting materials depending on the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve luminous efficiency up to four times that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

As the hole injecting layer, the hole transporting layer, the hole blocking layer, and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formulas are widely known and anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material . Particularly, as a phosphorescent material having a great advantage in improving the efficiency of a light emitting material, a metal complex compound containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like is used as a blue, green and red dopant material . So far, CBP has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of light emitting properties, but their glass transition temperature is low and their thermal stability is not very good, which is not satisfactory in terms of lifetime in organic EL devices.

Japanese Patent Application Laid-Open No. 2001-160489

In order to solve the above problems, the present invention aims at providing a novel organic compound which can be applied to an organic electroluminescent device and has excellent hole injecting ability, transporting ability, electron injecting ability, transporting ability and light emitting ability .

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage and a high luminous efficiency and having an improved lifetime.

In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).

In Formula 1,

X ₁ and X ₂ are the same or different and are each independently N (Ar ₁ ) or C (Ar ₂ ) (Ar ₃ ), wherein at least one of X ₁ and X ₂ is N (Ar ₁ );

Ar ₁ to Ar ₃ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of, or adjacent groups combine to form a condensed ring Can be;

Y ₁ to Y ₁₂ are the same or different and are each independently N or C;

a to c are each independently an integer of 0 to 4, and when a to c are each independently an integer of 1 to 3, R ₁ to R ₃ are the same as or different from each other and each independently represents a substituent selected from the group consisting of deuterium, halogen, A nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C An aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C of the group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of the C ₆₀ group and selected from the group consisting of C ₆ ~ C ₆₀ aryl amine, or, or in adjacent group bonded may form a fused ring, where R ₁ to R ₃ are respectively the case of a plurality, these same or Different and each;

Provided that at least one of R ₁ to R ₃ is selected from the group consisting of a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms;

The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group and arylsilyl group of Ar ₁ to Ar ₃ and R ₁ to R ₃ , An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, and an arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkynyl group, ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ one or more substituents selected from the group consisting of C ₆₀ arylamine And when the substituent is plural, they may be the same or different.

Also, the present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes an organic electroluminescent Device.

Here, the one or more organic layers may include a hole injecting layer, a hole transporting layer, a light emitting layer, a life improving layer, an electron transporting layer, and an electron injecting layer. In this case, Transporting layer, electron transporting layer, light emitting layer, or life improving layer.

The compound represented by the formula (1) according to the present invention has excellent thermal stability and luminescent properties and can be used as an organic material layer of an organic electroluminescent device.

In particular, when the compound represented by Formula 1 of the present invention is applied to an organic electroluminescent device, it is possible to manufacture an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long life, An improved full color display panel can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New compound

A novel compound according to the present invention is a 5-membered heterocyclic moiety in which benzene is condensed with dibenzo [b, f] azepine or 5H-dibenzo [a, d] cycloheptene moiety is condensed to form a basic skeleton and is represented by the general formula (1).

More specifically, the compound represented by the formula (1) may be prepared by condensation of an indole moiety with 5H-dibenzo [b, f] azepine or condensation of 5Hdibenzo [a, d] cycloheptene ), An indole moiety is condensed and each N is substituted with an aryl group (specifically, a phenyl group), a heteroaryl group, or an arylamine group, and the basic skeleton is a structure in which the structure is replaced with a basic skeleton .

The compound represented by the formula (1) has higher molecular weight than conventional organic electroluminescent device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')] But the hole injecting ability, hole transporting ability, and light emitting ability are excellent. Therefore, when the compound of Formula 1 is applied to an organic compound layer of an organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.

More specifically, the compound of Chemical Formula (1) according to the present invention can have excellent hole transporting ability and / or electron transporting ability as various kinds of substituents are introduced into a benzene ring which is not N in the basic skeleton. Accordingly, the compound of Formula 1 can be used as an organic material layer (specifically, a hole transport layer) of an organic electroluminescent device having hole mobility or electron mobility of a certain level or higher.

The compound of formula (I) according to the present invention is a compound represented by the general formula (1) wherein the benzene ring of the basic skeleton has a large electron absorbing property such as an aryl group, a nitrogen-containing heteroaryl group (e.g., pyridine group, pyrimidine group, triazine group, When an electron-attracting device (EWG) is combined, since the entire molecule has a bipolar characteristic, the binding force between holes and electrons can be enhanced. Accordingly, the compound of Formula 1 can exhibit excellent luminescent characteristics, and thus can be effectively applied to blue, green or red phosphorescent light-emitting layer materials of organic electroluminescent devices.

In the compound of formula (I) according to the present invention, when the carbon and nitrogen are directly bonded (C-N bond), the bond structure may be distorted or the conjugate may be broken as compared with the case where carbon and carbon are directly bonded (C-C bond). Accordingly, the compound of Formula 1 can extend the conjugated system by arranging the carbon of the basic skeleton and the carbon of the electron-attracting group (EWG) to bond, and as a result, the luminescent auxiliary material having a long- As shown in FIG.

Generally, in the phosphorescent light emitting layer of the organic electroluminescent device, the triplet energy gap of the host material must be higher than the triplet energy gap of the dopant material. That is, in order to effectively provide phosphorescent emission from the dopant, the lowest excitation state of the host must be higher energy than the lowest emission state of the dopant. The compound represented by the above formula (1) has a specific substituent group (for example, an aryl group, a heteroaryl group, or an arylamine group) introduced into a condensed indole moiety having a broad singlet energy level and a high triplet energy level, And can be used as a host material.

As described above, the compound represented by Formula 1 not only improves the phosphorescence characteristics of the organic electroluminescent device but also improves the hole injecting / transporting ability, luminous efficiency, driving voltage, lifetime characteristics and the like, The electron transporting ability and the like can be improved. Accordingly, the compound of Chemical Formula (1) according to the present invention is useful as an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), a hole and electron transport layer material, , A lifetime improving layer material, more preferably a phosphorescent light emitting layer material, a hole and an electron transporting layer material, and a life improving layer material.

In addition, the compound of Formula (1) has various substituents, especially an aryl group and / or a heteroaryl group, introduced into the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, For example, CBP). ≪ / RTI > The compound represented by the formula (1) is also effective for inhibiting crystallization of the organic material layer. Therefore, the organic electroluminescent device comprising the compound of Formula 1 according to the present invention can greatly improve performance and lifetime characteristics. As a result, the organic light emitting device having such improved performance and lifetime characteristics can maximize the performance of the full color organic light emitting panel.

That is, when the compound of Formula 1 according to the present invention is used as a hole and electron injection / transport layer material of an organic electroluminescent device or a blue, green and / or red phosphorescent host material, a conventional organic layer material (for example, CBP) The efficiency and lifetime of the organic electroluminescent device can be greatly improved. Further, such lifetime enhancement of the organic electroluminescent device can maximize the performance of the full color organic luminescent panel.

The novel compound according to the present invention is a compound represented by the above formula (1).

More specifically, in the compound represented by Formula 1, X ₁ and X ₂ are the same or different from each other and each independently N (Ar ₁ ) or C (Ar ₂ ) (Ar ₃ ). At least one of X ₁ and X ₂ is N (Ar ₁ ).

Ar ₁ to Ar ₃ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of, or adjacent groups combine to form a condensed ring . Preferably, Ar ₁ to Ar ₃ are the same or different and each independently represents hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms And an arylamine group of C ₆ to C ₆₀ , or may be bonded to an adjacent group to form a condensed ring.

Y ₁ to Y ₁₂ are the same or different and are each independently N or C; Preferably, Y ₁ to Y ₁₂ are all C's.

a to c are each independently an integer of 0 to 4; Here, when a to c are each independently 0, it means that hydrogen is not substituted with each substituent R ₁ to R ₃ . When each of a to c is independently an integer of 1 to 4, R ₁ to R ₃ are the same as or different from each other and each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ or an alkenyl group of C _40, C ₂ to C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 of to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ group of the C ₄₀ alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ Or may combine with adjacent groups to form a condensed ring, wherein when R ₁ to R ₃ are each plural, they are the same or different. Preferably, R ₁ to R ₃ are the same or different and each independently represents hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms And an arylamine group of C ₆ to C ₆₀ , or may be bonded to an adjacent group to form a condensed ring. Provided that at least one of R ₁ to R ₃ is selected from the group consisting of a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

In this case, the alkyl group of said Ar ₁ to Ar _3, R ₁ to R _3, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an aryl silyl groups, alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group , A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, aryl of C ₆ ~ C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylamine It may be substituted with a group, wherein when the substituent is plural, they may be the same or different from each other.

The compound represented by the formula (1) may be represented by the following formula (2) or (3).

In the above Formulas 2 and 3,

Ar ₁ to Ar ₃ , Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are as defined in Formula 1, respectively.

More specifically, the compound represented by the formula (2) may be represented by any one of the following formulas (4) to (7).

In the above formulas 4 to 7,

Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are as defined in Formula 1, respectively.

d and e are each independently an integer of 0 to 5, and f is an integer of 0 to 4. Here, when d to f are each independently 0, it means that hydrogen is not substituted with each of substituents R ₄ to R ₆ . When d and e are each independently an integer of 1 to 5 and f is an integer of 1 to 4, R ₄ to R ₆ are the same or different and are each independently selected from the group consisting of deuterium, a C ₁ to C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, or to the adjacent group bonded may form a fused ring, wherein R ₄ to R < ₆ > are plural, they are the same or different.

The compound represented by the formula (3) may be represented by any one of the following formulas (8) to (11).

In the general formulas (8) to (11)

Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are as defined in Formula 1, respectively.

f is an integer of 0 to 4; In this case, when f is 0, it means that hydrogen is not substituted with substituent R ₆ . Further, f is the case of 1 to 4 integer, R ₆ are each independently a heavy hydrogen, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ of C ₆₀ arylamine group, or may be bonded to adjacent groups to form a condensed ring. When R ₆ is plural, they are the same or different.

In the compound represented by Formula 1, at least one of Ar ₁ to Ar ₃ and R ₁ to R ₃ may be a substituent represented by Formula 12 below.

In Formula 12,

* Represents a moiety bonded to Formula 1 above.

L ₁ is a single bond or a group selected from the group consisting of a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms.

Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₇ ), provided that at least one of Z ₁ to Z ₅ is N, provided that when R ₇ is plural, It is different.

R ₇ is hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₆₀ heteroaryl group, -aryl silyl group of C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ of, C ₁ - C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine group, C ₆ of the C ₆₀ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an arylamine, or a C _60, or by bonding adjacent groups may form a condensed ring.

Here, the arylene group and a heteroarylene group, an alkyl group of R _7, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group of L _1, alkylsilyl group , aryl silyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently selected from deuterium, halogen, cyano, C alkyl group of _{1 ~ C 40, C 2 ~} C 40 alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 of the heteroaryl A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ line from the group consisting of C ₆₀ arylamine When the first plurality may be substituted, and wherein the substituents of the substituents of two or more, they may be the same or different from each other.

The substituent represented by the formula (12) may be further represented by any one of substituents represented by the following formulas (A1) to (A15). However, it is not particularly limited.

In the formulas (A1) to (A15), L ₁ and R ₇ are the same as defined in the above formula (12).

n is an integer of 0 to 4; In this case, when n is 0, it means that hydrogen is not substituted with substituent R ₈ . When n is an integer of 1 to 4, R ₈ is each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of, or by an adjacent group bonded may form a condensed ring, Here, when a plurality of R < ₈ > are plural, they are the same or different from each other.

In this case, the alkyl group of said R _8, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an arylboronic The arylphosphine oxide group and the arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl , A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group , A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group , C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine can be substituted by one or more substituent species selected from the group consisting of It said, at this time if the plurality of substituents, they may be the same or different from each other.

Thus, the compounds represented by the formula (1) according to the present invention are represented by the following compounds A-1 to A-10, B-1 to B-10, C-1 to C-10, D-1 to D- E-1 to E-10, and F-1 to F-10. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples of such alkynyls include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl; N-imidazolyl; 2-isoxazolyl; 2-pyridinyl; 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and R represents aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and may be a linear, branched or cyclic structure . ≪ / RTI > Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "alkylboron" means boron substituted with alkyl having 1 to 40 carbon atoms, and "arylboron" means boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compound represented by formula (1) of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.

2. Organic Field  Light emitting element

The present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).

More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, a life improving layer, an electron transporting layer and an electron injecting layer. . ≪ / RTI > Specifically, the organic compound layer containing the compound of Formula 1 is preferably a light emitting layer, an electron transporting layer, a hole transporting layer, and a life improving layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material (preferably, a phosphorescent host material), which may include a compound of the above formula (1) as a host material. The light emitting layer of the organic electroluminescent device of the present invention may contain a compound other than the compound of Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode are sequentially stacked . At this time, a light emitting auxiliary layer may intervene between the hole transporting layer and the light emitting layer, and a life improving layer may be interposed between the light emitting layer and the electron transporting layer. In addition, an electron injection layer may be further stacked on the electron transport layer. One or more of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the lifetime improving layer, the electron transporting layer and the electron injecting layer may include the compound represented by the above formula (1) A light emitting layer, and a life improving layer may include a compound represented by the above formula (1). Here, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula have.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and ordinary materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[ Preparation Example  One] EIAz - 1 of  synthesis

≪ Step 1 > 5-phenyl-5H- dibenzo [b, f] azepine  Synthesis of

Iodobenzene (126.7 g, 621.0 mmol), Cu (16.4 g, 258.7 mmol), K ₂ CO ₃ (143.0 g, 1,035.0 mmol), and a mixture of 5H-dibenzo [b, f] azepine (100 g, 517.5 mmol) nitrobenzene (1000 ml) were mixed and stirred at 210 캜 for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and then concentrated and recrystallized from ethanol to obtain 5-phenyl-5H-dibenzo [b, f] azepine (100.4 g, yield 72%).

^{1 H-NMR: δ 6.63-6.81 (} m, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.20 (d, 2H), 7.26-7.45 (m, 8H)

≪ Step 2 > 6-phenyl-6,10b- dihydro - 1aH - dibenzo [b, f] oxirno [2,3-d] azepine  Synthesis of

(100 g, 372.6 mmol), meta- chloroperoxybenzoic acid (mCPBA) (77.2 g, 447.1 mmol), silica (200.7 g), NaOCl (200.7 g) and acetonitrile (ACN) (1000 ml) were mixed and stirred at 80 ° C for 2 hours.

After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and recrystallized from ethanol to obtain 6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3- d] azepine (84.0 g, yield 79%).

¹ H-NMR:? 4.31 (s, 2H), 6.63-6.81 (m, 3H), 7.24-7.53 (m,

≪ Step 3 > 5-phenyl-5H- dibenzo [b, f] azepine -10 (11H) - one's  synthesis

(84.0 g, 294.3 mmol) and lithium iodide (LiI) (47.3 g, 353.2 mmol) in a stream of nitrogen were added to a solution of 6-phenyl-6,10b-dihydro- And chloroform (CHL) (840 ml) were mixed and stirred at 60 ° C for 1 hour.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and recrystallized in ethanol to obtain 68.0 g (yield: 81%) of 5-phenyl-5H-dibenzo [b, f] azepin- ≪ / RTI >

^{1 H-NMR: δ 3.42 (} d, 1H), 4.21 (d, 1H), 6.62-6.74 (m, 3H), 7.25-7.40 (m, 7H), 7.51-7.59 (m, 2H), 8.10 (d , 1H)

<Step 4> Synthesis of 5-phenyl-10,11- (5- chloro -1H- indole ) -5H- dibenzo [b, f] azepine  Synthesis of

Biphenyl-10 (11H) -one (68.0 g, 238.4 mmol) and (4-chlorophenyl) hydrazine (37.4 g, 262.3 mmol) and acetic acid (700 ml) were added thereto, followed by stirring at 120 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5-phenyl-10,11- (5-chloro-1H- indole) -5H-dibenzo [ , f] azepin (66.5 g, 71% yield).

¹ H-NMR:? 6.63-6.69 (m, 4H), 6.81-6.87 (m, 3H), 6.98 , 7.68 (s, IH), 8.83 (d, IH), 11.36 (b, IH)

<Step 5> Synthesis of 5-phenyl-10,11- (5- chloro -1-phenyl-1H- indole ) -5H-dibenzo [b, f] azepin

5H-dibenzo [b, f] azepine (66.5 g, 169.3 mmol), iodobenzene (41.4 g, 203.1 mmol), Cu (5.4 g, 84.6 mmol), K ₂ CO ₃ (46.8 g, 338.6 mmol) and nitrobenzene (665 ml) were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 5-phenyl-10,11- (5-chloro- -dibenzo [b, f] azepin (58.0 g, yield 73%).

^{1 H-NMR: δ 6.63-6.69 (} m, 4H), 6.81-6.87 (m, 3H), 7.16-7.20 (m, 5H), 7.45-7.69 (m, 8H), 8.83 (d, 1H)

<Step 6> EIAz - 1 of  synthesis

5-dibenzo [b, f] azepine (57.8 g, 123.6 mmol), 4,4,4 ', 4'- (34.5 g, 135.9 mmol), Pd (dppf) Cl ₂ (10.8 g, 12.4 mmol), 5,5,5,5,5-octamethyl-2,2'- , KOAc (34.9 g, 370.7 mmol) and 1,4-dioxane (600 ml) were mixed and stirred at 130 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain EIAz-1 (56.1 g, yield 81% .

^{1 H-NMR: δ 1.24 (} s, 12H), 6.63-6.69 (m, 4H), 6.81-6.87 (m, 3H), 7.16-7.20 (m, 4H), 7.45-7.60 (m, 8H), 7.71 (d, 1 H), 8.83 (d, 1 H)

[ Preparation Example  2] EIAz - 2 of  synthesis

<Step 1> Synthesis of 1- (4- klorophenyl ) -1H- indole  Synthesis of

1-chloro-4-iodobenzene (244.3 g, 1024.8 mmol), Cu (27.2 g, 427.0 mmol), K ₂ CO ₃ (236.1 g, 1.70 mol) and nitrobenzene (3000 ml) were mixed and stirred at 210 占 폚 for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 8: 1 (v / v)) to obtain 1- (4-chlorophenyl) 163.3 g, yield 84%).

^{1 H-NMR: δ 6.52 (} d, 1H), 6.87 (dd, 1H), 7.33-7.37 (m, 3H), 7.49 (d, 2H), 7.60 (d, 1H), 7.93-7.94 (m, 2H )

&Lt; Step 2 > 2- chloro -5H- dibenzo [b, f] azepine  Synthesis of

1- (4-chlorophenyl) -1H-indole (163.3 g, 717.4 mmol) and polyphosphoric acid (PPA) (817 g) were mixed in a nitrogen stream and stirred at 100 ° C for 12 hours.

After the reaction was completed, it was extracted from water and then filtered to obtain 2-chloro-5H-dibenzo [b, f] azepine (49 g, yield 30%).

^{1 H-NMR: δ 6.57 (} d, 1H), 6.81 (dd, 1H), 6.99-7.09 (m, 4H), 7.17 (s, 1H), 7.25 (d, 1H), 8.21 (d, 1H), 8.42 (b, 1 H)

<Step 3> 2- chloro -5-phenyl-5H- dibenzo [b, f] azepine  Synthesis of

(49.5 g, 215.2 mmol), iodobenzene (52.7 g, 258.1 mmol), Cu (6.8 g, 107.6 mmol), K ₂ CO ₃ (59.5 g, 430 mmol) and nitrobenzene (1000 ml) were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to obtain 2-chloro-5-phenyl-5H-dibenzo [ b, f] azepine (52.3 g, yield 80%).

^{1 H-NMR: δ 6.57-6.63 (} m, 4H), 6.80-6.81 (m, 2H), 6.99-7.09 (m, 4H), 7.17-7.25 (m, 4H)

&Lt; Step 4 > 3- chloro -6-phenyl-6,10b- dihydro - 1aH - dibenzo [b, f] oxirno Synthesis of [2,3-d] azepine

(52.6 g, 172.1 mmol), meta- chloroperoxybenzoic acid (35.6 g, 206.5 mmol), silica (104.6 g), NaOCl (104.6 g) and acetonitrile (550 ml) were mixed and stirred at 80 ° C for 2 hours.

After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was recrystallized from ethanol to obtain 45.1 g (yield: 82%) of 3-chloro-6-phenyl-6,10b-dihydro-1aH- dibenzo [b, f] oxireno [2,3- &Lt; / RTI &gt;

^{1 H-NMR: δ 4.20 (} s, 2H), 6.63-6.56 (m, 4H), 6.74-6.81 (m, 2H), 7.11-7.20 (m, 5H), 7.31 (s, 1H)

<Step 5> 2- chloro -5-phenyl-5H- dibenzo [b, f] azepine -10 (11H) - one's  synthesis

(45.1 g, 141.1 mmol) and lithium iodide (22.7 g, 169.3 mmol) in a stream of nitrogen under a stream of nitrogen, ) And chloroform (500 ml) were mixed and stirred at 60 ° C for 1 hour.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was recrystallized from ethanol to obtain 38.4 g of 2-chloro-5-phenyl-5H-dibenzo [b, f] azepin- Yield: 85%).

^{1 H-NMR: δ 3.80 (} s, 2H), 6.45 (d, 1H), 6.63 (d, 2H), 6.74-6.81 (m, 2H), 6.92 (dd, 1H), 7.05 (d, 1H), 7.18-7.20 (m, 3H), 7.39 (dd, IH), 7.54 (d, IH)

<Step 6> Synthesis of 2- chloro -5-phenyl-10,11- (1-phenyl-1H- indole ) -5H-dibenzo [b, f] azepin

(38.4 g, 120.0 mmol), 1,1-diphenylhydrazine (24.3 g, 131.9 mmol), and acetic acid were added to a solution of 2-chloro-5-phenyl-5H-dibenzo [b, f] azepin- (400 ml) was added thereto, followed by stirring at 120 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 2-chloro-5-phenyl-10,11- (1-phenyl- -dibenzo [b, f] azepin (42.8 g, yield 76%).

^{1 H-NMR: δ 6.63-6.69 (} m, 4H), 6.81-6.87 (m, 2H), 7.16-7.20 (m, 4H), 7.42-7.58 (m, 7H), 7.71-7.76 (m, 2H) , 8.17 (d, 1 H), 8.83 (d, 1 H)

<Step 7> EIAz - 2 of  synthesis

5H-dibenzo [b, f] azepine (42.8 g, 91.1 mmol), 4,4,4 ', 4'- (25.5 g, 100.3 mmol), Pd (dppf) Cl ₂ (8.0 g, 9.1 mmol), 5,5,5,5,5-octamethyl-2,2'-bi (1,3,2-dioxaborolane) , KOAc (25.7 g, 273.5 mmol) and 1,4-dioxane (400 ml) were mixed and stirred at 130 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain EIAz-2 (39.9 g, yield 78% .

¹ H-NMR:? 1.24 (s, 12H), 6.63-6.69 (m, 4H), 6.81-6.87 (m, 2H), 7.16-7.20 (m, 3H), 7.41-7.58 (d, 1 H), 8.17 (d, 1 H), 8.83 (d, 1 H)

[ Preparation Example  3] EIAz - 3 of  synthesis

&Lt; Step 1 > 5-H- Dibenzo [a, d] cycloheptene  Synthesis of

After mixing 5-dibenzosuberenone (100g, 484.9 mmol ), N 2 H 2 · H 2 O (830 mL) in a nitrogen stream and sealed reaction vessel was stirred at 180 ℃ for 15 hours.

After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, dried over MgSO ₄ and precipitated with methanol to obtain 5-H-Dibenzo [a, d] cycloheptene (69.9 g, yield 75%).

^{1 H-NMR: δ 3.51 (} s, 2H), 6.99 (s, 2H), 7.07 (d, 2H), 7.18 (dd, 2H), 7.26 (dd, 2H), 7.38 (d, 2H)

&Lt; Step 2 > 5,5- dimethyl -5-H- Dibenzo [a, d] cycloheptene  Synthesis of

Methyl iodide (MeI) (103.2 g, 727.3 mmol) and KI (6.64 g, 40.0 mmol) were mixed with 5-H-Dibenzo [a, d] cycloheptene (69.9 g, 363.7 mmol) and DMSO (1000 mL) mmol) is added dropwise and the reaction temperature is lowered to 0 ° C. KOH (85.7 g, 1,527.3 mmol) was added and the mixture was stirred at 0 ° C for 15 minutes, then heated to room temperature and stirred for 15 hours. Methyl iodide (34.6 g, 243.6 mmol) was added thereto, followed by stirring at 60 ° C for 7 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to obtain 5,5- a, d] cycloheptene (51.3 g, yield 62%).

^{1 H-NMR: δ 1.72 (} s, 6H), 6.99 (s, 2H), 7.22-7.30 (m, 6H), 7.42 (d, 2H)

&Lt; Step 3 > dimethyl -6,10b- dihydro - 1aH - dibenzo [b, f] oxirno Synthesis of [2,3-d] cycloheptene

(51.3 g, 225.5 mmol), meta- chloroperoxybenzoic acid (46.7 g, 270.6 mmol), silica (102.7 g), NaOCl (102.7 g) and acetonitrile (513.4 ml) were mixed and stirred at 80 ° C for 2 hours.

After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and recrystallized with ethanol to obtain 41.6 g (78% yield) of 6,6-dimethyl-6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] cycloheptene .

^{1 H-NMR: δ 1.72 (} s, 6H), 4.20 (s, 2H) 6.99 (s, 2H), 7.20-7.30 (m, 6H), 7.59 (d, 2H)

&Lt; Step 4 > dimethyl -5-H- Dibenzo [a, d] cycloheptane -10 (11H) - one's  synthesis

Dibenzo [b, f] oxireno [2,3-d] cycloheptene (41.6 g, 175.9 mmol) and lithium iodide (28.2 g, 211.0 mmol) in a nitrogen stream and a solution of 6,6-dimethyl-6,10b-dihydro- chloroform (500 ml) were mixed and stirred at 60 ° C for 1 hour.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and recrystallized in ethanol to obtain 5,5-dimethyl-5-H-Dibenzo [a, d] cycloheptane-10 (11H) Yield: 75%).

^{1 H-NMR: δ 1.72 (} s, 6H), 3.81 (s, 2H) 7.18 (dd, 1H), 7.38-7.44 (m, 4H), 7.54-7.56 (m, 2H), 7.86 (d, 1H)

<Step 5> EIAz - 3 of  synthesis

(31.2 g, 131.2 mmol), phenylhydrazine (15.7 g, 145.1 mmol), and acetic acid (350 ml) were added under a stream of nitrogen, And the mixture was stirred at 120 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain EIAz-3 (26.5 g, yield 65%).

^{1 H-NMR: δ 1.72 (} s, 6H), 7.06-7.08 (m, 2H), 7.33-7.44 (m, 7H), 7.56-7.60 (m, 2H), 7.71 (d, 1H), 11.36 (b , 1H)

[ Preparation Example  4] EIAz Synthesis of -4

<Step 1> to <Step 4>

The same procedure as in <Step 1> to <Step 4> of Preparation Example 3 was performed.

<Step 5> EIAz - 4 of  synthesis

(31.2 g, 131.2 mmol), naphthalen-1-ylhydrazine (23.0 g, 145.1 mmol), and acetic acid (10 mL) were added to a solution of 5,5-dimethyl-5-H-Dibenzo [a, d] cycloheptane- (350 ml), and the mixture was stirred at 120 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain EIAz-4 (26.1 g, yield 55%).

¹ H-NMR:? 1.72 (s, 6H), 7.33-7.36 (m, 6H), 7.60-7.71 (m, 6H), 8.16 (d, )

[ Preparation Example  5] EIAz Synthesis of -5

<Step 1> to <Step 4>

The same procedure as in <Step 1> to <Step 4> of Preparation Example 3 was performed.

&Lt; Step 5 > 5,5- dimethyl -10,11- (5- chloro -1H- indole ) -5-H-Dibenzo [a, d] cycloheptene Synthesis

(31.2 g, 131.2 mmol) and (4-chlorophenyl) hydrazine (20.7 g, 145.1 mmol) and acetic acid were added to a solution of 5,5-dimethyl-5-H-Dibenzo [a, d] cycloheptane- acid (350 ml) was added thereto, followed by stirring at 120 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain 5,5-dimethyl-10,11- (5-chloro-1H- indole) -Dibenzo [a, d] cycloheptene (26.8 g, yield 59%).

^{1 H-NMR: δ 1.72 (} s, 6H), 6.98 (d, 1H), 7.33-7.38 (m, 7H), 7.60 (d, 1H), 7.68-7.71 (m, 2H), 11.36 (b, 1H )

&Lt; Step 6 > dimethyl -10,11- (5- chloro -1-phenyl-1H- indole ) -5-H-Dibenzo [a, d] cycloheptene Synthesis

5-H-Dibenzo [a, d] cycloheptene (26.8 g, 77.8 mmol), iodobenzene (19.2 g, 93.4 mmol) , Cu (2.5 g, 38.9 mmol), K ₂ CO ₃ (21.5 g, 155.6 mmol) and nitrobenzene (300 ml) were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain 5,5-dimethyl-10,11- (5-chloro- -5-H-Dibenzo [a, d] cycloheptene (24.5 g, yield 75%).

^{1 H-NMR: δ 1.72 (} s, 6H), 7.18 (d, 1H), 7.33-7.38 (m, 6H), 7.45-7.71 (m, 9H)

<Step 7> EIAz - 5 of  synthesis

5-H-Dibenzo [a, d] cycloheptene (24.5 g, 58.4 mmol), 4,4- (16.3 g, 64.2 mmol), Pd (dppf) Cl ₂ (5.1 g, 16.2 mmol), 4 ', 4', 5,5,5 &apos;, 5 ' , 5.8 mmol), KOAc (16.5 g, 175.1 mmol) and 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain EIAz-5 (23.3 g, yield 78% .

^{1 H-NMR: δ 1.24 (} s, 12H), 1.72 (s, 6H), 7.33-7.36 (m, 6H), 7.45-7.50 (. M 3H), 7.58-7.60 (m, 5H), 7.71-7.72 (m, 2H)

[ Synthetic example  1] Synthesis of A-1

Synthesized from Preparation Example 1 was conducted in a nitrogen atmosphere EIAz-1 (3.8 g, 6.7 mmol), 4- (biphenyl-4-yl) -6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (PPh 3) ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol) and toluene / EtOH / H ₂ O (50/30/20 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with MC, and then water was removed with MgSO _{4. The} residue was purified by recrystallization to obtain target compound A-1 (3.5 g, yield 71%).

Mass (theory: 740.89, measurement: 740 g / mol)

[ Synthetic example  2] Synthesis of A-2

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6-chloro-2- The procedure of Example 1 was repeated to obtain the target compound A-2 (3.3 g, yield 73%).

Mass (theory: 665.78, found: 665 g / mol)

[ Synthetic example  3] Synthesis of A-3

Was obtained in the same manner as in Synthesis Example 1, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- (3.8 g, yield 77%) as a target compound A-3.

Mass (theory: 740.89, measurement: 740 g / mol)

[ Synthetic example  4] Synthesis of A-4

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound A-4 (3.5 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass (theory value: 741.88, measurement: 741 g / mol)

[ Synthetic example  5] Synthesis of A-5

2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound A-5 (3.6 g, yield 72%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass (theory value: 741.88, measurement: 741 g / mol)

[ Synthetic example  6] Synthesis of A-6

4-yl) -6- (4-bromophenyl) -2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound A-6 (3.7 g, yield 68%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass (theory: 816.98, measured: 816 g / mol)

[ Synthetic example  7] Synthesis of A-7

(Biphenyl-4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3,5-triazine in place of 4- (biphenyl-4-yl) -6- , 8.0 mmol), the target compound A-7 (4.3 g, yield 79%) was obtained.

Mass (theory: 817.97, measured: 817 g / mol)

[ Synthetic example  8] Synthesis of A-8

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) was used in the place of 4- (biphenyl-4-yl) -6- ) Was used instead of the compound A-8 (3.6 g, yield 65%) as a target compound.

Mass (theory: 817.97, measured: 817 g / mol)

[ Synthetic example  9] Synthesis of A-9

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- To obtain phosphorus A-9 (1.9 g, yield 67%).

Mass (theory: 638.75, found: 638 g / mol)

[ Synthetic example  10] Synthesis of A-10

The procedure of Synthesis Example 1 was repeated except that 2- (3-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- Compound A-10 (3.5 g, yield 70%) was obtained.

Mass (theory: 736.9, measured: 736 g / mol)

[ Synthetic example  11] Synthesis of B-1

(3.8 g, 6.7 mmol), 4- (biphenyl-4-yl) -6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol) synthesized in Preparation Example 2 and Pd (PPh ₃ ) ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol) and toluene / EtOH / H ₂ O (50/30/20 ml) were mixed and stirred at 110 ° C for 5 hours. After the reaction was completed, the reaction mixture was extracted with MC, and then water was removed with MgSO _{4. The} residue was purified by recrystallization to obtain the target compound B-1 (3.2 g, yield 65%).

Mass (theory: 740.89, measurement: 740 g / mol)

[ Synthetic example  12] Synthesis of B-2

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6-chloro-2- The procedure of Example 11 was repeated to obtain the target compound B-2 (3.1 g, yield 70%).

Mass (theory: 665.78, found: 665 g / mol)

[ Synthetic example  13] Synthesis of B-3

Was obtained in the same manner as in Synthesis Example 11, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- To obtain the target compound B-3 (3.7 g, yield 75%).

Mass (theory: 740.89, measurement: 740 g / mol)

[ Synthetic example  14] Synthesis of B-4

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound B-4 (3.4 g, yield 68%) was obtained by carrying out the same procedure as in Synthesis Example 11.

Mass (theory value: 741.88, measurement: 741 g / mol)

[ Synthetic example  15] Synthesis of B-5

2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound B-5 (3.6 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 11.

Mass (theory value: 741.88, measurement: 741 g / mol)

[ Synthetic example  16] Synthesis of B-6

4-yl) -6- (4-bromophenyl) -2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound B-6 (3.9 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 11.

Mass (theory: 816.98, measured: 816 g / mol)

[ Synthetic example  17] Synthesis of B-7

(Biphenyl-4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3,5-triazine in place of 4- (biphenyl-4-yl) -6- , 8.0 mmol), the target compound B-7 (4.1 g, yield 75%) was obtained.

Mass (theory: 817.97, measured: 817 g / mol)

[ Synthetic example  18] Synthesis of B-8

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) was used in the place of 4- (biphenyl-4-yl) -6- ), The target compound B-8 (3.7 g, yield 68%) was obtained by carrying out the same procedure as in Synthesis Example 11.

Mass (theory: 817.97, measured: 817 g / mol)

[ Synthetic example  19] Synthesis of B-9

The procedure of Synthesis Example 11 was repeated except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- B-9 (3.2 g, yield 74%).

Mass (theory: 638.75, found: 638 g / mol)

[ Synthetic example  20] Synthesis of B-10

The procedure of Synthesis Example 11 was repeated except that 2- (3-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- Compound B-10 (3.4 g, yield 69%) was obtained.

Mass (theory: 736.9, measured: 736 g / mol)

[ Synthetic example  21] Synthesis of C-1

The EIAz-3 prepared in Preparation Example 3 was conducted in a nitrogen atmosphere (2.1 g, 6.7 mmol), 4- (biphenyl-4-yl) -6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (OAc) 2 (0.08 g, 0.34 mmol), P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) Lt; / RTI &gt; After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound C-1 (2.8 g, yield 68%).

Mass (theory: 615.76, measured: 615 g / mol)

[ Synthetic example  22] Synthesis of C-2

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6-chloro-2- The procedure of Example 21 was repeated to obtain the target compound C-2 (2.3 g, yield 64%).

Mass (theory: 540.65, measured: 540 g / mol)

[ Synthetic example  23] Synthesis of C-3

Was obtained in the same manner as in Synthesis Example 21, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- To obtain C-3 (3.0 g, yield 73%) as a target compound.

Mass (theory: 615.76, measured: 615 g / mol)

[ Synthetic example  24] Synthesis of C-4

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound C-4 (2.7 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 21.

Mass (theory: 616.75, found: 616 g / mol)

[ Synthetic example  25] Synthesis of C-5

2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound C-5 (2.9 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 21.

Mass (theory: 616.75, found: 616 g / mol)

[ Synthetic example  26] Synthesis of C-6

4-yl) -6- (4-bromophenyl) -2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound C-6 (3.1 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 21.

Mass (theory: 691.85, measured: 691 g / mol)

[ Synthetic example  27] Synthesis of C-7

(Biphenyl-4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3,5-triazine in place of 4- (biphenyl-4-yl) -6- , 8.0 mmol), the target compound C-7 (3.3 g, yield 72%) was obtained.

Mass (theory: 692.84, measured: 692 g / mol)

[ Synthetic example  28] Synthesis of C-8

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) was used in the place of 4- (biphenyl-4-yl) -6- ), The target compound C-8 (3.5 g, yield 75%) was obtained by carrying out the same procedure as in Synthesis Example 21.

Mass (theory: 692.84, measured: 692 g / mol)

[ Synthetic example  29] Synthesis of C-9

The procedure of Synthesis Example 21 was repeated except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- C-9 (2.5 g, yield 73%) was obtained.

Mass (theory: 513.62, measurement: 513 g / mol)

[ Synthetic example  30] Synthesis of C-10

The procedure of Synthesis Example 21 was repeated except that 2- (3-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- Compound C-10 (2.8 g, yield 68%) was obtained.

Mass (theory: 611.8, measurement: 611 g / mol)

[ Synthetic example  31] Synthesis of D-1

Synthesized from Preparation Example 4 was conducted in a nitrogen atmosphere EIAz-4 (2.4 g, 6.7 mmol), 4- (biphenyl-4-yl) -6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (OAc) 2 (0.08 g, 0.34 mmol), P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) Lt; / RTI &gt; After completion of the reaction, toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound D-1 (3.2 g, yield 72%).

Mass (theory: 665.82, found: 665 g / mol)

[ Synthetic example  32] Synthesis of D-2

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6-chloro-2- The procedure of Example 31 was repeated to obtain the target compound D-2 (3.0 g, yield 75%).

Mass (theory: 590.71, measurement: 590 g / mol)

[ Synthetic example  33] Synthesis of D-3

Was obtained in the same manner as in Synthesis Example 31, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- To obtain the target compound D-3 (3.1 g, yield 70%).

Mass (theory: 665.82, found: 665 g / mol)

[ Synthetic example  34] Synthesis of D-4

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound D-4 (3.0 g, yield 68%) was obtained in the same manner as in Synthesis Example 31.

Mass (theory: 666.81, measurement: 666 g / mol)

[ Synthetic example  35] Synthesis of D-5

2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound D-5 (3.3 g, yield 74%) was obtained by carrying out the same procedure as in Synthesis Example 31.

Mass (theory: 666.81, measurement: 666 g / mol)

[ Synthetic example  36] Synthesis of D-6

4-yl) -6- (4-bromophenyl) -2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound D-6 (3.6 g, yield 72%) was obtained in the same manner as in Synthesis Example 31.

Mass (theory value: 741.91, measurement: 741 g / mol)

[ Synthetic example  37] Synthesis of D-7

(Biphenyl-4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3,5-triazine in place of 4- (biphenyl-4-yl) -6- , 8.0 mmol), D-7 (3.5 g, yield 70%) was obtained in the same manner as in Synthesis Example 31.

Mass (theory: 742.90, found: 742 g / mol)

[ Synthetic example  38] Synthesis of D-8

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) was used in the place of 4- (biphenyl-4-yl) -6- ), The target compound D-8 (3.4 g, yield 69%) was obtained by carrying out the same procedure as in Synthesis Example 31.

Mass (theory: 742.90, found: 742 g / mol)

[ Synthetic example  39] Synthesis of D-9

The procedure of Synthesis Example 31 was repeated except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- Of D-9 (2.8 g, yield 75%).

Mass (theory: 563.68, measurement: 563 g / mol)

[ Synthetic example  40] Synthesis of D-10

The procedure of Synthesis Example 31 was repeated except that 2- (3-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- To obtain compound D-10 (3.2 g, yield 72%).

Mass (theory: 661.83, found: 661 g / mol)

[ Synthetic example  41] Synthesis of E-1

4-yl-6-chloro-2-phenylpyrimidine (2.74 g, 8.0 mmol), Pd (PPh ₃ ), prepared in Preparation Example 5, ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol) and toluene / EtOH / H ₂ O (50/30/20 ml) were mixed and stirred at 110 ° C for 5 hours. After the reaction was completed, the reaction mixture was extracted with MC, and then water was removed with MgSO _{4. The} residue was purified by recrystallization to obtain the target compound E-1 (3.2 g, yield 68%).

Mass (theory: 691.86, measurement: 691 g / mol)

[ Synthetic example  42] Synthesis of E-2

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6-chloro-2- The target compound E-2 (3.1 g, yield 75%) was obtained in the same manner as in Example 41.

Mass (theory: 616.75, found: 616 g / mol)

[ Synthetic example  43] Synthesis of E-3

Was obtained in the same manner as in Synthesis Example 41, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- To obtain the target compound E-3 (3.2 g, yield 69%).

Mass (theory: 691.86, measurement: 691 g / mol)

[ Synthetic example  44] Synthesis of E-4

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound E-4 (3.4 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 41.

Mass (theory: 692.85, measured: 692 g / mol)

[ Synthetic example  45] Synthesis of E-5

2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The objective compound E-5 (3.2 g, yield 70%) was obtained.

Mass (theory: 692.85, measured: 692 g / mol)

[ Synthetic example  46] Synthesis of E-6

4-yl) -6- (4-bromophenyl) -2-phenylpyrimidine (3.7 g, 8.0 mmol) instead of 4- (biphenyl-4-yl) -6-chloro-2- , The target compound E-6 (3.3 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 41.

Mass (theory: 767.95, found: 767 g / mol)

[ Synthetic example  47] Synthesis of E-7

(Biphenyl-4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3,5-triazine in place of 4- (biphenyl-4-yl) -6- , 8.0 mmol), the target compound E-7 (3.6 g, yield 70%) was obtained.

Mass (theory: 768.94, measured: 768 g / mol)

[ Synthetic example  48] Synthesis of E-8

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) was used in the place of 4- (biphenyl-4-yl) -6- ), The target compound E-8 (3.8 g, yield 74%) was obtained in the same manner as in Synthesis Example 41.

Mass (theory: 768.94, measured: 768 g / mol)

[ Synthetic example  49] Synthesis of E-9

The procedure of Synthesis Example 41 was repeated except that 2-chloro-4-phenylquinazoline (2.9 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- E-9 (2.7 g, yield 68%).

Mass (theory: 589.72, measurement: 589 g / mol)

[ Synthetic example  50] Synthesis of E-10

The procedure of Synthesis Example 41 was repeated except that 2- (3-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 4- (biphenyl-4-yl) -6- To obtain compound E-10 (3.3 g, yield 72%).

Mass (theory: 687.87, found: 687 g / mol)

[ Synthetic example  51] Synthesis of F-1

(3.8 g, 6.7 mmol), N, N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol) synthesized in Preparation Example 1, Pd (PPh ₃ ) ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol) and toluene / EtOH / H ₂ O (50/30/20 ml) were mixed and stirred at 110 ° C. for 5 hours Respectively. After completion of the reaction, the reaction mixture was extracted with MC. Then, water was removed with MgSO ₄ and purified by recrystallization to obtain the target compound F-1 (3.9 g, yield 65%).

Mass (theory: 906.12, measurement: 906 g / mol)

[ Synthetic example  52] F- 2 of  synthesis

4-yl) -N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) instead of N, N-di (biphenyl- (3.6 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 51, except that

Mass (theory: 803.99, measurement: 804 g / mol)

[ Synthetic example  53] F- 3 of  synthesis

(3.8 g, 6.7 mmol), N, N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol) synthesized in Preparation Example 2, Pd (PPh ₃ ) ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol) and toluene / EtOH / H ₂ O (50/30/20 ml) were mixed and stirred at 110 ° C. for 5 hours Respectively. After the reaction was completed, the reaction mixture was extracted with MC, and then water was removed with MgSO _{4. The} residue was purified by recrystallization to obtain the target compound F-3 (4.2 g, yield 70%).

Mass (theory: 906.12, measurement: 906 g / mol)

[ Synthetic example  54] F- 4 of  synthesis

(4'-bromobiphenyl-4-yl) -N-phenylnaphthalen-1-amine instead of N- (4'-bromobiphenyl- 4 (3.4 g, yield 63%) was obtained by carrying out the same procedure as in Synthetic Example 53, except that the title compound was used in an amount of 3.6 g (8.0 mmol) instead of 4- .

Mass (theory: 803.99, measurement: 804 g / mol)

[ Synthetic example  55] Synthesis of F-5

(2.1 g, 6.7 mmol), N, N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol) synthesized in Preparation Example 3, Pd _{(OAc) 2 (0.08 g,} 0.34 mmol), P (t -Bu) 3 (0.16 ml, 0.67 mmol), NaO (t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) mixture, and 110 to Lt; 0 &gt; C for 5 hours. After the reaction was completed, toluenen was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound F-5 (3.5 g, yield 66%).

Mass (theory: 780.99, measured: 780 g / mol)

[ Synthetic example  56] Synthesis of F-6

4-yl) -N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) instead of N, N-di (biphenyl- The procedure of Synthesis Example 55 was repeated to obtain the target compound F-6 (3.0 g, yield 65%).

Mass (theory: 678.86, found: 678 g / mol)

[ Synthetic example  57] Synthesis of F-7

(2.4 g, 6.7 mmol), N, N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol) synthesized in Preparation Example 4, Pd _{(OAc) 2 (0.08 g,} 0.34 mmol), P (t -Bu) 3 (0.16 ml, 0.67 mmol), NaO (t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) mixture, and 110 to Lt; 0 &gt; C for 5 hours. After completion of the reaction, toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound F-7 (3.3 g, yield 60%).

Mass (theory: 831.05, measurement: 831 g / mol)

[ Synthetic example  58] Synthesis of F-8

4-yl) -N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) instead of N, N-di (biphenyl- The procedure of Synthesis Example 57 was repeated to obtain the target compound F-8 (3.5 g, yield 71%).

Mass (theory: 728.92, measurement: 728 g / mol)

[ Synthetic example  59] Synthesis of F-9

(3.4 g, 6.7 mmol), N, N-di (biphenyl-4-yl) -4'-chlorobiphenyl-4-amine (4.1 g, 8.0 mmol) synthesized in Preparation Example 5, Pd (PPh ₃ ) ₄ (0.39 g, 0.34 mmol), K ₂ CO ₃ (2.32 g, 16.75 mmol) and toluene / EtOH / H ₂ O (50/30/20 ml) were mixed and stirred at 110 ° C. for 5 hours Respectively. After the reaction was completed, the reaction mixture was extracted with MC, and then water was removed with MgSO _{4. The} residue was purified by recrystallization to obtain the target compound F-9 (3.8 g, yield 67%).

Mass (theory: 857.09, found: 857 g / mol)

[ Synthetic example  60] Synthesis of F-10

4-yl) -N-phenylnaphthalen-1-amine (3.6 g, 8.0 mmol) instead of N, N-di (biphenyl- The procedure of Synthesis Example 59 was repeated to obtain the target compound F-10 (3.2 g, yield 64%).

Mass (theory: 754.96, measurement: 754 g / mol)

[ Example  1 to 45] green organic Field  Manufacturing of light emitting device

The compounds A-1 to A-8, A-10, B-1 to B-8, B-10, C-1 to C-8, C-10, D-1 to D- D-10, E-1 to E-8, and E-10 were subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) thin film having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

A-10, B-1 to B-8, and B-8 of m-MTDATA (60 nm) / TCTA (80 nm) / 90% on each ITO transparent electrode prepared as described above. Ir (ppy) ₃ (300 nm), Ir-10, C-1 to C-8, C-10, D-1 to D-8, D-10, E-1 to E- / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  1] Green organic Field  Manufacturing of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound A-1 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP, Alq ₃ and BCP used in Examples 1 to 45 and Comparative Example 1 are as follows.

[ Evaluation example  One]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the green organic electroluminescent devices prepared in Examples 1 to 45 and Comparative Example 1, respectively, and the results are shown in Tables 1 and 2 .

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 A-1 6.86 518 38.9 Example 2 A-2 6.48 518 41.3 Example 3 A-3 6.48 517 41.3 Example 4 A-4 6.86 515 41.3 Example 5 A-5 6.77 518 41.2 Example 6 A-6 6.66 518 38.9 Example 7 A-7 6.65 517 41.3 Example 8 A-8 6.77 515 41.2 Example 9 A-10 6.77 518 38.9 Example 10 B-1 6.66 518 41.3 Example 11 B-2 6.65 517 41.3 Example 12 B-3 6.77 515 41.3 Example 13 B-4 6.66 518 41.2 Example 14 B-5 6.66 518 38.9 Example 15 B-6 6.81 517 41.3 Example 16 B-7 6.68 515 41.3 Example 17 B-8 6.66 518 41.3 Example 18 B-10 6.70 518 41.2 Example 19 C-1 6.66 517 42.2 Example 20 C-2 6.66 515 42.0 Example 21 C-3 6.81 518 39.7 Example 22 C-4 6.68 518 38.9 Example 23 C-5 6.66 518 41.3 Example 24 C-6 6.70 517 41.3 Example 25 C-7 6.70 515 43.1 Example 26 C-8 6.51 518 43.5 Example 27 C-10 6.77 518 41.4 Example 28 D-1 6.70 517 43.1 Example 29 D-2 6.51 515 41.3 Example 30 D-3 6.77 515 41.3 Example 31 D-4 6.46 515 41.3 Example 32 D-5 6.51 515 41.2 Example 33 D-6 6.77 518 38.9 Example 34 D-7 6.70 518 41.3 Example 35 D-8 6.51 517 41.3 Example 36 D-10 6.77 515 41.3

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 37 E-1 6.86 518 41.2 Example 38 E-2 6.77 517 42.0 Example 39 E-3 6.66 518 39.7 Example 40 E-4 6.66 517 38.9 Example 41 E-5 6.77 518 41.3 Example 42 E-6 6.70 518 41.3 Example 43 E-7 6.51 518 43.1 Example 44 E-8 6.77 517 41.3 Example 45 E-10 6.77 518 38.9 Comparative Example 1 CBP 6.93 516 38.2

As shown in Tables 1 and 2, the green organic electroluminescent devices (Examples 1 to 45) using the compound according to the present invention in the light emitting layer are superior to the green organic electroluminescent device (Comparative Example 1) using CBP as the light emitting layer It was confirmed that the current efficiency and the driving voltage were excellent.

[ Example  46 to 50] Red organic Field  Manufacturing of light emitting device

The compounds A-9, B-9, C-9, D-9 and E-9 synthesized in the synthesis examples were subjected to high purity sublimation purification by a conventionally known method and then red organic electroluminescent devices were manufactured according to the following procedure .

First, a glass substrate coated with ITO (Indium tin oxide) thin film having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

B-9, C-9, D-9, E-9 + 10% of m-MTDATA (60 nm) / TCTA (80 nm) / 90% by _{piq) 2 Ir (acac) (} 300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) stacked in order to prepare an organic electroluminescent device.

[ Comparative Example  2]

A red organic electroluminescent device was manufactured in the same manner as in Example 46 except that CBP was used instead of the compound A-9 as a luminescent host material in forming the light emitting layer.

The structures of (piq) ₂ Ir (acac) used in Examples 46 to 50 and Comparative Example 2 are as follows.

[ Evaluation example  2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for the organic electroluminescent devices prepared in Examples 46 to 50 and Comparative Example 2, respectively, and the results are shown in Table 3 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 46 A-9 4.94 12.5 Example 47 B-9 4.81 10.8 Example 48 C-9 4.64 13.2 Example 49 D-9 4.87 11.9 Example 50 E-9 4.78 13.1 Comparative Example 2 CBP 5.25 8.2

As shown in Table 3, the red organic electroluminescent devices (Examples 46 to 50) using the compound according to the present invention in the light emitting layer had a higher current efficiency than the red organic electroluminescent device using the CBP as the light emitting layer (Comparative Example 2) And the driving voltage were excellent.

[ Example  51 to 60] Organic Field  Manufacturing of light emitting device

Compounds F-1 to F-10 synthesized in Synthesis Example were subjected to high purity sublimation purification by a conventionally known method, and then an organic electroluminescent device was manufactured according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes And the substrate was transferred to the back vacuum deposition machine.

DS-501 (Doosan Electronics, 30 nm) / 5% of m-MTDATA (60 nm) / each of the compounds F-1 to F-10 (80 nm) / DS- The organic electroluminescent device was fabricated by stacking BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

[ Comparative Example  3] Organic Field  Manufacturing of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Example 51 except that NPB was used instead of the compound F-1 as the hole transport layer material in forming the hole transport layer.

The structure of NPB used in Comparative Example 3 is as follows.

[ Evaluation example  3]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 51 to 60 and Comparative Example 3, respectively, and the results are shown in Table 4 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 51 F-1 4.9 21.1 Example 52 F-2 4.6 19.4 Example 53 F-3 4.8 20.0 Example 54 F-4 4.3 19.3 Example 55 F-5 4.8 19.2 Example 56 F-6 4.6 21.1 Example 57 F-7 4.8 19.4 Example 58 F-8 4.3 20.0 Example 59 F-9 4.6 19.3 Example 60 F-10 4.8 19.2 Comparative Example 3 NPB 5.2 18.1

As shown in Table 4, the organic electroluminescent devices (Examples 51 to 60) using the compound according to the present invention as the hole transporting layer were superior to the organic electroluminescent device using the NPB as the hole transporting layer (Comparative Example 3) And the driving voltage were excellent.

[ Example  61 to 100] Blue organic Field  Manufacturing of light emitting device

The compounds A-1 to A-8, B-1 to B-8, C-1 to C-8, D-1 to D-8 and E-1 to E- After the high-purity sublimation purification was performed, a blue organic electroluminescent device was produced as follows.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

DS-405 (Doosan Electronics Co., Ltd.) (30 nm) / each of Compound A-5% of DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / AND + 5% 1 to A-8, B-1 to B-8, C-1 to C-8, D-1 to D-8, E-1 to E-8 (5 nm) / Alq ₃ (1 nm) / Al (200 nm) in this order to form an organic electroluminescent device.

[ Comparative Example  4] Blue organic Field  Manufacturing of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 61, except that the lifetime improving layer was not formed and Alq ₃ , which is an electron transporting layer material, was deposited at 30 nm instead of 25 nm.

[ Comparative Example  5] Blue organic Field  Manufacturing of light emitting device

Lifetime Improvement in the Formation of the Life-improving Layer A blue organic electroluminescent device was produced in the same manner as in Example 61 except that BCP was used instead of Compound A-1 as a layer material.

The structure of the AND used in Examples 61 to 100 and Comparative Examples 4 and 5 is as follows.

[ Evaluation example  4]

The driving voltage, current efficiency, light emitting wavelength and lifetime (T ₉₇ ) at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 61 to 100 and Comparative Examples 4 and 5, Are shown in Tables 5 and 6 below.

Sample Life improvement layer The driving voltage (V) Current efficiency (cd / A) Emission peak (nm) Lifetime (hr, T ₉₇ ) Example 61 A-1 4.3 6.2 459 38 Example 62 A-2 4.2 6.1 451 37 Example 63 A-3 4.4 6.1 460 32 Example 64 A-4 4.3 6.0 461 39 Example 65 A-5 4.3 6.1 461 44 Example 66 A-6 4.2 6.3 462 45 Example 67 A-7 4.7 6.1 463 32 Example 68 A-8 4.3 6.1 457 39 Example 69 B-1 4.6 6.2 459 38 Example 70 B-2 4.5 6.0 459 37 Example 71 B-3 4.8 6.1 459 32 Example 72 B-4 4.3 6.1 451 39 Example 73 B-5 4.4 6.3 459 44 Example 74 B-6 4.3 6.0 459 45 Example 75 B-7 4.2 6.2 459 45 Example 76 B-8 4.2 6.1 451 32 Example 77 C-1 4.3 6.1 460 39 Example 78 C-2 4.7 6.0 460 38 Example 79 C-3 4.2 6.1 459 37 Example 80 C-4 4.8 6.2 459 32 Example 81 C-5 4.9 6.1 451 39 Example 82 C-6 4.5 6.1 460 44 Example 83 C-7 4.3 6.0 461 42 Example 84 C-8 4.2 6.0 461 44 Example 85 D-1 4.2 6.0 462 43 Example 86 D-2 4.9 6.2 463 48 Example 87 D-3 4.6 6.4 460 49 Example 88 D-4 4.3 6.0 459 41 Example 89 D-5 4.6 6.0 459 48 Example 90 D-6 4.3 6.0 451 49 Example 91 D-7 4.1 6.2 460 41 Example 92 D-8 4.3 6.4 461 42

Sample Life improvement layer The driving voltage (V) Current efficiency (cd / A) Emission peak (nm) Lifetime (hr, T ₉₇ ) Example 93 E-1 4.2 6.3 461 47 Example 94 E-2 4.4 6.4 462 43 Example 95 E-3 4.8 6.2 463 48 Example 96 E-4 4.4 6.1 469 49 Example 97 E-5 4.7 6.0 461 41 Example 98 E-6 4.5 6.0 462 48 Example 99 E-7 4.9 6.0 463 49 Example 100 E-8 4.6 6.0 469 41 Comparative Example 4 - 4.7 5.6 458 32 Comparative Example 5 BCP 5.3 5.9 458 28

As shown in Tables 5 and 6, the blue organic electroluminescent devices (Examples 61 to 100) in which the compound according to the present invention was used for the life improving layer (Examples 61 to 100) (Comparative Example 5) in which the conventional BCP was used for the lifetime improving layer, as compared with the conventional organic electroluminescent device (Comparative Example 5), and the lifetime was remarkably improved I could confirm.

[ Example  101 to 110] blue organic Field  Manufacturing of light emitting device

The compounds A-1, A-6, B-1, B-6, C-1, C-6, D-1, D-6, E- , The blue organic electroluminescent device was prepared as described below.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

DS-405 (Doosan Electronics Co., Ltd.) (30 nm) / each of Compound A-5% of DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / AND + 5% (30 nm) / LiF (1 nm) / Al (1 nm), A-6, B-1, B-6, C-1, C-6, D- 200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  6] blue organic Field  Manufacturing of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 101 except that Alq ₃ was used instead of Compound A-1 as an electron transporting layer material in forming the electron transporting layer.

[ Evaluation example  5]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices prepared in Examples 101 to 110 and Comparative Example 6, respectively, and the results are shown in Table 7 below.

Sample Electron transport layer The driving voltage (V) Current Efficiency (V) Emission peak (nm) Example 101 A-1 4.2 6.3 462 Example 102 A-6 4.0 6.1 460 Example 103 B-1 4.1 5.8 457 Example 104 B-6 4.6 5.8 463 Example 105 C-1 4.5 6.1 460 Example 106 C-6 4.6 5.8 457 Example 107 D-1 4.5 5.8 463 Example 108 D-6 4.2 5.8 462 Example 109 E-1 4.0 6.0 460 Example 110 E-6 4.1 6.1 463 Comparative Example 6 - 4.7 5.6 458

As shown in Table 7, the blue organic electroluminescent devices (Examples 101 to 110) using the compound according to the present invention as the electron transport layer were driven in comparison with the blue organic electroluminescent device (Comparative Example 4) Voltage and current efficiency.

As described above, it was confirmed that the organic electroluminescent device using the compound represented by the formula (1) according to the present invention in the lifetime improving layer and the electron transporting layer can improve the driving voltage and the current efficiency, and further improve the lifetime characteristics.

Claims (9)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X ₁ and X ₂ are the same or different and are each independently N (Ar ₁ ) or C (Ar ₂ ) (Ar ₃ ), wherein at least one of X ₁ and X ₂ is N (Ar ₁ );
Ar ₁ to Ar ₃ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of, or adjacent groups combine to form a condensed ring Can be;
Y ₁ to Y ₁₂ are the same or different and are each independently N or C;
a to c are each independently an integer of 0 to 4, and when a to c are each independently an integer of 1 to 3, R ₁ to R ₃ are the same as or different from each other and each independently represents a substituent selected from the group consisting of deuterium, halogen, A nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C An aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C of the group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of the C ₆₀ group and selected from the group consisting of C ₆ ~ C ₆₀ aryl amine, or, or in adjacent group bonded may form a fused ring, where R ₁ to R ₃ are respectively the case of a plurality, these same or Different and each;
Provided that at least one of R ₁ to R ₃ is selected from the group consisting of a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms;
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group and arylsilyl group of Ar ₁ to Ar ₃ and R ₁ to R ₃ , An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, and an arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkynyl group, ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ one or more substituents selected from the group consisting of C ₆₀ arylamine And when the substituent is plural, they may be the same or different. The method according to claim 1,
Wherein Ar ₁ to Ar ₃ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and C ₆ of each other An arylamine group having a carbon number of 1 to ₆₀ , or may be bonded to an adjacent group to form a condensed ring;
Wherein R ₁ to R ₃ are the same or different and are each independently hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, a heteroaryl group of nuclear atoms of 5 to 60 and C ₆ of the Or an arylamine group having a carbon number of 1 to ₆₀ , or may be bonded to an adjacent group to form a condensed ring,
The alkyl, aryl, heteroaryl and arylamine groups of Ar ₁ to Ar ₃ and R ₁ to R ₃ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroatom having 5 to 60 nuclear atoms An aryl group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkyl boron group, one member selected from the group consisting of C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ with an aryl amine of the C ₆₀ of the And when the substituent is plural, they may be the same or different from each other. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)

(3)

In the above Formulas 2 and 3,
Ar ₁ to Ar ₃ , Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are as defined in claim 1, respectively. The method of claim 3,
Wherein the compound represented by Formula 2 is represented by any one of the following Formulas 4 to 7:
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 4 to 7,
Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are each as defined in claim 1;
d and e are each independently an integer of 0 to 5, f is an integer of 0 to 4, d to f are each independently an integer of 1 to 5, f is an integer of 1 to 4, R ₄ to R ₆ are the same or different and are each independently selected from the group consisting of deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and an arylamine group of C ₆ to C ₆₀ Or may combine with adjacent groups to form a condensed ring, wherein when each of R ₄ to R ₆ is plural, they are the same or different The method of claim 3,
Wherein the compound represented by the formula (3) is represented by any one of the following formulas (8) to (11):
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the general formulas (8) to (11)
Y ₁ to Y ₁₂ , a to c, and R ₁ to R ₃ are each as defined in claim 1;
f is an integer of 0 to 4, and when f is an integer of 1 to 4, R ₆ is each independently selected from the group consisting of deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A heteroaryl group, and an arylamine group having ₆ to ₆₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring. When R ₆ is plural, they are the same or different. The method according to claim 1,
Wherein at least one of Ar ₁ to Ar ₃ and R ₁ to R ₃ is a substituent represented by the following formula (12):
[Chemical Formula 12]

In Formula 12,
* Represents a moiety bonded to Formula 1;
L ₁ is a single bond or a group selected from the group consisting of a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Z ₁ to Z ₅ are the same as or different from each other and each independently N or C (R ₇ ), provided that at least one of Z ₁ to Z ₅ is N, and when R ₇ is plural, Different;
R ₇ is hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₆₀ heteroaryl group, -aryl silyl group of C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ of, C ₁ - C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine group, C ₆ of the C ₆₀ ~ C aryl phosphine oxide ₆₀ group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine, or, or in adjacent groups combine to form a condensed ring;
Aryl group and a heteroaryl group of the alkylene group, R ₇ of the L _1, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an aryl silyl groups, alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group , A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, group C ₆ to C ₆₀ aryl boronic, C ₆ to C ₆₀ aryl phosphine group of, C ₆ to C ₆₀ aryl phosphine oxide group, and a C ₆ to C ₆₀ aryl amine group selected from the group consisting of 1 If it may be substituted with one substituent, wherein the substituent of the plurality, they may be the same or different from each other. The method according to claim 6,
Wherein the substituent of the formula (12) is represented by any one of the substituents represented by the following formulas (A1) to (A15):

In the above formulas A1 to A15,
L ₁ and R ₇ are as defined in claim 6;
n is an integer of 0 to 4, and when n is an integer of 1 to 4, R ₈ is each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ heteroaryl group of C ₆₀ aryl group, the nuclear atoms of 5 to 60, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ of the aryloxy group, an alkyl boronic of C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide ₆₀ group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, or adjacent groups bonded to the condensation of And when R ₈ is plural, they may be the same or different from each other;
Alkyl group of the R _8, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C of ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ may be substituted by one or more substituents selected from the group consisting of an aryl amine of the C ₆₀ of, For the substituent, when a plurality, they may be the same or different from each other. An organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein at least one organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting layer, a life improving layer, an electron transporting layer, and an electron injecting layer.