KR20180041361A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more specifically, to a novel organic compound with excellent luminous power, and an organic electroluminescent device having improved characteristics such as high luminous efficiency, low driving voltage, and long lifetime by containing the novel compound in one or more organic material layers.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device using the organic compound.

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a compound having excellent light-emitting ability and a compound having at least one organic compound in the organic compound layer, Device.

A study on organic electroluminescent devices that resulted in blue electroluminescence using anthracene single crystals in 1965 based on observation of organic thin film emission of Bernanose in the 1950s was made by Tang in 1987 divided by the functional layer of the hole layer and the light emitting layer An organic electroluminescent device having a laminated structure has been proposed. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials 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 at 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 electroluminescent device can be classified into blue, green and red light emitting materials according to 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 the luminous efficiency up to 4 times as compared with that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq ₃ and the like represented by the following chemical formulas are widely known as substances used as a hole blocking layer and an electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host materials. As a phosphorescent dopant material having a great advantage in terms of efficiency improvement 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 a blue, green, It is used as a material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional luminescent materials are advantageous from the viewpoint of luminescence characteristics, but they are not satisfactory in terms of lifetime in an organic electroluminescent device because the glass transition temperature is low and the thermal stability is not very good. Therefore, development of a luminescent material having excellent performance is required.

Japanese Patent Application Laid-Open No. 2001-160489

In order to solve the above problems, it is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and has excellent 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).

[Chemical Formula 1]

In Formula 1,

L ₁ and L ₂ are the same or different and are each independently 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 nucleus atoms,

Plural R ₁ are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group and C ₂ ~ C Or an alkynyl group having 1 to ₄₀ carbon atoms, or may be bonded to adjacent groups to form a condensed ring, but at least one condensed ring is formed,

B is a substituent represented by the following formula (2)

(2)

In Formula 2,

* Represents a moiety bonded to Formula 1,

X is selected from the group consisting of C (R ₃ ) (R ₄ ), O and S,

Ar ₁ and Ar ₂ are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ alkynyl group of C _40, C 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 ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C the group of boron ₆₀ aryl, C ₆ ~ C ₆₀ aryl phosphine group, is selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of,

m is an integer of 0 to 3,

R ₂ to R ₄ are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ alkynyl group of C _40, C 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 ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group of ₆₀ arylboronic, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of or, or adjacent groups bonded fused to the A ring can be formed,

Wherein L _1, and arylene group of L ₂ and a heteroarylene group, an alkyl group of said Ar ₁ and Ar _2, R ₁ to R _4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, 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 C ₆ -C An arylamine group having 1 to ₆₀ carbon atoms, and when the substituent is plural, they may be the same or different from each other.

The present invention also provides an organic electroluminescent device comprising 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 a compound represented by the general formula An electroluminescent device is provided. Here, the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. At this time, the compound represented by Formula 1 may be used as a phosphorescent host of the light emitting layer.

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

In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer lifetime than conventional host materials can be manufactured. Further, This improved full color display panel can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel organic compound according to the present invention can be produced by directly coupling 'acridine, phenoxazine or phenothiazine' to 'benzocarbazole' or linker (eg, arylene group or hetero Arylene group), and a variety of substituents are introduced into the basic skeleton to be represented by the formula (1).

Specifically, the compound of formula (1) includes acridine, phenoxazine or phenoxyazine having sublimation properties and excellent thermal stability. When the compound of Formula 1 is used in an organic electroluminescent device, the lifetime of the device is prolonged and can be used for a long time.

Compounds of formula (I) can be conjugated with acridine, phenoxazine or phenoxyazine to form benzoglucarb which is conjugated with band gap ) Can be reduced. In addition, the compound of Formula 1 is bonded to 'acridine, phenoxazine or phenoxyazine' by benzocarbazole to increase the conjugation length compared to the case of binding to 'carbazole' band gap can be reduced (see Table 1 below). The compound of Formula 1 may be used as an organic material layer of an organic electroluminescent device, and when used as a light emitting layer material, it may exhibit a long wavelength and be used as a red phosphorescent host material.

rescue

　

HOMO 5.02 eV 4.48 eV 5.04 eV 4.66 eV LUMO 2.01 eV 2.01 eV 2.10 eV 2.00 eV Band gap 3.01 eV 2.47 eV 2.94 eV 2.66 eV T1 2.37 eV 2.15 eV 2.42 eV 2.26 eV

In addition, the compound of Formula 1 can control HOMO and LUMO energy levels according to various types of substituents introduced into the basic skeleton, and can have a wide band gap as well as a high carrier transportability. When the electron donating group (EWG) having a high electron absorbing property such as a nitrogen-containing heterocycle (for example, a pyridine group, a pyrimidine group, a quinazoline group or a triazine group) is bonded to the basic skeleton, Since the entire molecule has a bipolar characteristic, the bonding force between holes and electrons can be enhanced. The compound of the formula (1) can be used as an organic material layer material of an organic electroluminescence device, particularly a light emitting layer material.

The compound represented by the formula (1) has higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as "CBP")] But also has excellent luminous efficiency. Accordingly, when the compound of Formula 1 is applied to an organic material layer of an organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved. The compound of the formula (1) can be used as an organic layer material of an organic electroluminescence device, and can preferably be used as a light emitting layer material (blue, green and / or red phosphorescent host material).

Accordingly, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifetime characteristics, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize the performance.

The novel compounds according to the present invention are represented by the above formula (1) in which various substituents are introduced into benzocarbazole through acridine, phenoxazine or phenoxyazine directly or through a linker.

Specifically, in the compound represented by Formula 1, L ₁ and L ₂ may be the same or different and each independently a single bond or a divalent linking group. Wherein the bivalent linking group is selected from the group consisting of C ₆ to C ₁₈ arylene groups and heteroarylene groups having 5 to 18 nuclear atoms. Examples of the arylene group and the heteroarylene group include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenylene group, a carbazolylene group, a thiophenylene group, An imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group and the like.

Preferably, L < _{1 >} and L < ₂ &_gt; are the same as or different from each other, and each independently may be a single bond or a C ₆ -C ₁₈ arylene group.

Plural R ₁ are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group and C ₂ ~ C Or an alkynyl group having 1 to ₄₀ carbon atoms, or may be bonded to adjacent groups to form a condensed ring, but at least one condensed ring is formed.

Preferably, the plurality of R ₁ forms a fused ring one by one and the other of R ₁ R ₁ is bonded, and the remaining R ₁ may be hydrogen. The compound of the formula (1) may be embodied as a compound represented by the following formulas (3) to (8).

X is selected from the group consisting of C (R ₁ ) (R ₂ ), O and S.

Ar ₁ and Ar ₂ are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ alkynyl group of C _40, C 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 ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C ₆₀ arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, is selected from C ₆ ~ C ₆₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of.

Preferably, Ar ₁ and Ar ₂ are the same or different and each independently represents 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 C ₆ To C ₆₀ arylamine groups. More preferably, Ar ₁ may be a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms, and Ar ₂ may be a C ₆ to C ₆₀ aryl group. When Ar ₁ is a heteroaryl group and Ar ₂ is an aryl group, when Ar ₁ is an aryl group and Ar ₂ is a heteroaryl group, or both Ar ₁ and Ar ₂ are C ₆ to C ₆₀ heteroaryl The bandgap can be further reduced compared to the case of ' Such a compound can be used as a light emitting layer material of an organic electroluminescent device, and can be preferably used as a red phosphorescent host material.

and m is an integer of 0 to 3. In this case, when m is 0, it means that hydrogen is not substituted with substituent R ₂ . when m is an integer of 1 to 3, it means that the substituent is hydrogen substituted with R _2, and R ₂ are the same or different, each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C _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 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 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 of the group, C ₁ ~ C ₄₀ group of an 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 ~ C ₆₀ of the And an arylamine group.

R ₃ and R ₄ are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ alkynyl group of C _40, C 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 ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group of ₆₀ arylboronic, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of or, or adjacent groups bonded fused to the A ring can be formed.

Preferably, R ₃ and R ₄ are the same or different from each other and each independently represents hydrogen, deuterium (D), halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₆ to C ₆₀ aryl group, a 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 of, or adjacent groups combine to form a condensed ring.

Wherein L _1, and arylene group of L ₂ and a heteroarylene group, an alkyl group of said Ar ₁ and Ar _2, R ₁ to R _4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, 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 C ₆ -C An arylamine group having 1 to ₆₀ carbon atoms, and when the substituent is plural, they may be the same or different from each other.

The compound represented by the formula (1) may be embodied as at least one of the following formulas (3) to (5). However, it is not particularly limited.

(3)

[Chemical Formula 4]

[Chemical Formula 5]

Wherein L ₁ , L ₂ , Ar ₁ , Ar ₂ , m and R ₂ are the same as defined in the above formula (1).

Further, the compound represented by the formula (1) may be further formulated into at least one of the following formulas (6) to (8). However, it is not particularly limited.

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In Formula 6 to 8, L ₁ , L ₂ , Ar ₁ , Ar ₂ , m and R ₂ are as defined in Formula 1, respectively.

According to a preferred embodiment of the present invention, Ar ₁ may be a substituent represented by the following general formula (9).

[Chemical Formula 9]

In the above formula (9), * denotes a moiety bonded to the formula (1).

Z ₁ to Z ₅ are the same as or different from each other and each independently N or C (R ₅ ), wherein when R ₅ is plural, they are the same as or different from each other.

R ₅ is hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of the A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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 An 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, a C ₆ to C ₆₀ An arylphosphine group, an arylphosphine oxide group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring.

Alkyl groups of the R _5, 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 a heavy hydrogen (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C _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 alkenyl group, C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, substituted with one or more substituents selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of And when the substituent is plural, they may be the same or different from each other.

The substituent represented by the above formula (9) may be further formulated by any one of the following A-1 to A-15. However, it is not particularly limited.

In the above A-1 to A-15, R < ₅ >

p is an integer of 0 to 4; When p is 0, it means that hydrogen is not substituted with substituent R ₆ . If the p is 1 to 4 integer, R ₆ is deuterium (D), a halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ alkyloxy 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 ~ selected from the group consisting of an aryl amine of the C ₆₀ or, or the group bonded adjacent to form a condensed ring And when R < ₆ > is plural, they may be the same or different from each other.

Alkyl group of the R _6, 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 a heavy hydrogen (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C _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 alkenyl group, C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, substituted with one or more substituents selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of And when the substituent is plural, they may be the same or different from each other.

The compound represented by the formula (1) of the present invention described above can be further represented by a compound represented by any one of the following compounds 1 to 576. 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.

&Quot; 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.

&Quot; 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, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 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-, and R 'means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include linear, branched or cyclic structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

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

&Quot; 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.

&Quot; 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" is 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, "alkyl boron" is boron substituted with alkyl having 1 to 40 carbon atoms, and "aryl boron" 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, and "arylphosphine oxide group" means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O do.

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 include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. have. Specifically, the organic compound layer containing the compound of Formula 1 is preferably a light emitting layer.

The light emitting layer of the organic electroluminescence device of the present invention may include a host material (preferably, a phosphorescent 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 auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially stacked . At least one of the hole injecting layer, the hole transporting layer, the light-emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, ≪ / RTI > compounds. Here, an electron injection layer may be further stacked on the electron transport layer. Further, 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 1] Core 1 of  synthesis

(50 g, 168.82 mmol), (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) boronic acid (55.58 g, 168.82 mmol) _{mmol), Pd (PPh 3)} 4 (9.76 g, 5 mol%) , NaOH (20.26 g, 506.47 mmol) were dissolved in _{THF / H 2 O (400 ml} / 100 ml) was stirred at 80 for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, Core 1 (72.7 g, yield 86%) was obtained by column chromatography.

^{1 H-NMR: δ 1.68 (} s, 6H), 7.14 (m, 9H), 7.33 (d, 1H), 7.69 (m, 5H), 7.74 (m, 2H), 7.86 (s, 1H), 7.95 ( d, 2H), 8.52 (d, 1H), 11.63 (s, 1H)

[ Preparation Example 2] Core 2 of  synthesis

(9,9-dimethyl-10-phenyl-9,10-dihydroacridin-3-yl) boronic acid was used instead of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin- , 168.82 mmol) was used as a starting material, to obtain Core 2 (69.3 g, yield 82%).

^{1 H-NMR: δ 1.68 (} s, 6H), 7.11 (m, 12H), 7.62 (m, 4H), 7.74 (d, 1H), 7.85 (s, 1H), 7.97 (d, 2H), 8.56 ( d, 1 H), 11.63 (s, 1 H)

[ Preparation Example 3] Core 3 of  synthesis

Phenyl-10H-phenoxazin-3-yl) boronic acid (51.2 g, 168.8 mmol) was used instead of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin- , Core 3 (67.3 g, yield 84%) was obtained in the same manner as in Preparation Example 1, except that

¹ H-NMR:? 7.19 (m, 12H), 7.58 (m, 4H), 7.76 (d, s, 1 H)

[ Preparation Example 4] Core 4 of  synthesis

Phenyl-10H-phenoxazin-2-yl) boronic acid (51.2 g, 168.8 mmol) instead of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin- , Core 4 (63.3 g, yield 79%) was obtained in the same manner as in Preparation Example 1, except that

¹ H-NMR:? 7.17 (m, 12H), 7.57 (m, 4H), 7.74 (d, s, 1 H)

[ Preparation Example 5] Core 5 of  synthesis

Phenyl-10H-phenothiazin-3-yl) boronic acid (53.9 g, 168.8 mmol) was used in place of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin- , Core 5 (68.7 g, yield 83%) was obtained in the same manner as in Preparation Example 1, except that

¹ H-NMR:? 7.18 (m, 12H), 7.58 (m, 4H), 7.75 (d,

[ Preparation Example 6] Core 6 of  synthesis

10-phenyl-10H-phenothiazin-2-yl) boronic acid (53.9 g, 168.8 mmol) was used instead of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin- , Core 6 (67.1 g, yield 81%) was obtained in the same manner as in Preparation Example 1, except that

^{1 H-NMR: δ 7.13 (} m, 11H), 7.34 (d, 1H), 7.57 (m, 4H), 7.78 (d, 1H), 7.85 (s, 1H), 7.97 (d, 2H), 8.52 ( d, 1 H), 11.63 (s, 1 H)

[ Preparation Example 7] Core 7's  synthesis

The procedure of Preparation Example 1 was repeated except that 9-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used in place of 10-bromo-7H- g, yield: 82%).

^{1 H-NMR: δ 1.68 (} s, 6H), 7.17 (m, 9H), 7.35 (d, 1H), 7.57 (m, 5H), 7.75 (s, 2H), 7.95 (d, 2H), 8.34 ( d, 1 H), 11.63 (s, 1 H)

[ Preparation Example 8] Core 8 of  synthesis

The procedure of Preparation Example 2 was repeated except that 9-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used instead of 10-bromo-7H- g, yield 78%).

¹ H-NMR:? 1.68 (s, 6H), 7.18 (m, 12H), 7.57 (m, 4H), 7.72 d, 1 H), 11.63 (s, 1 H)

[ Preparation Example 9] Core 9 of  synthesis

The procedure of Preparation Example 3 was repeated except that 9-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo- g, yield: 80%).

¹ H-NMR:? 7.19 (m, 12H), 7.55 (m, 4H), 7.96 (d, 2H), 8.29

[ Preparation Example 10] Core Ten  synthesis

The procedure of Preparation Example 4 was repeated except that 9-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used in place of 10-bromo-7H- g, yield: 76%).

¹ H-NMR:? 7.21 (m, 12H), 7.57 (m, 4H), 7.72 (s, s, 1 H)

[ Preparation Example 11] Core Eleven  synthesis

The procedure of Preparation Example 5 was repeated except that 9-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H- g, yield: 81%).

¹ H-NMR:? 7.29 (m, 12H), 7.57 (m, 4H), 7.72 (s, s, 1 H)

[ Preparation Example 12] Core 12 of  synthesis

The procedure of Preparation Example 6 was repeated except that 9-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H- g, yield: 77%).

^{1 H-NMR: δ 7.17 (} m, 11H), 7.37 (d, 1H), 7.57 (m, 4H), 7.79 (s, 1H), 8.01 (d, 2H), 8.34 (d, 1H), 8.57 ( d, 1 H), 11.63 (s, 1 H)

[ Preparation Example 13] Core Thirteen  synthesis

The procedure of Preparation Example 1 was repeated except that 8-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used in place of 10-bromo-7H- g, yield: 72%).

^{1 H-NMR: δ 1.68 (} s, 6H), 7.13 (m, 9H), 7.34 (d, 1H), 7.52 (m, 6H), 7.79 (s, 1H), 8.01 (d, 2H), 8.27 ( d, 1 H), 8.53 (d, 1 H), 11.63 (s, 1 H)

[ Preparation Example 14] Core 14 of  synthesis

The procedure of Preparation Example 2 was repeated except that 8-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used in place of 10-bromo-7H- g, yield 68%).

¹ H-NMR:? 7.17 (m, 12H), 7.56 (m, 5H), 8.03 (d, 2H), 8.27

[ Preparation Example 15] Core Fifteen  synthesis

The procedure of Preparation Example 3 was repeated except that 8-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo-7H- g, yield 70%).

¹ H-NMR:? 7.17 (m, 12H), 7.57 (m, 5H), 8.02 (d, 2H), 8.28

[ Preparation Example 16] Core 16  synthesis

The procedure of Preparation Example 4 was repeated except that 8-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo-7H- g, yield 66%).

¹ H-NMR:? 7.18 (m, 12H), 7.54 (m, 5H), 8.02 (d, 2H), 8.28

[ Preparation Example 17] Core 17  synthesis

The procedure of Preparation Example 5 was repeated except that 8-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H- g, yield 69%).

¹ H-NMR:? 7.43 (m, 17H), 8.07 (d, 2H), 8.27 (d,

[ Preparation Example 18] Core 18  synthesis

The procedure of Preparation Example 6 was repeated except that 8-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used in place of 10-bromo-7H- g, yield: 63%).

^{1 H-NMR: δ 7.21 (} m, 11H), 7.37 (d, 1H), 7.52 (m, 5H), 8.03 (d, 2H), 8.23 (d, 1H), 8.55 (d, 1H), 11.63 ( s, 1 H)

[ Preparation Example 19] Core 19's  synthesis

The procedure of Preparation Example 1 was repeated except that 11-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used in place of 10-bromo-7H- g, yield: 74%).

^{1 H-NMR: δ 1.68 (} s, 6H), 7.11 (m, 9H), 7.37 (d, 1H), 7.52 (m, 8H), 7.94 (d, 2H), 8.32 (d, 1H), 11.63 ( s, 1 H)

[ Preparation Example 20] Core Twenty  synthesis

The procedure of Preparation Example 2 was repeated except that 11-bromo-7H-benzo [c] carbazole (55.58 g, 168.82 mmol) was used in place of 10-bromo-7H- g, yield 69%).

¹ H-NMR:? 1.68 (s, 6H), 7.11 (m, 9H), 7.36 (d, s, 1 H)

[ Preparation Example 21] Core 21  synthesis

The procedure of Preparation Example 3 was repeated except that 11-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo-7H- g, yield: 72%).

¹ H-NMR:? 7.16 (m, 12H), 7.67 (m, 5H), 7.92

[ Preparation Example 22] Core 22 of  synthesis

The same procedure as in Preparation Example 4 was carried out except that 11-bromo-7H-benzo [c] carbazole (51.2 g, 168.8 mmol) was used in place of 10-bromo-7H- g, yield 66%).

¹ H-NMR:? 7.11 (m, 12H), 7.67 (m, 6H), 7.97

[ Preparation Example 23] Core 23 of  synthesis

The procedure of Preparation Example 5 was repeated except that 11-bromo-7H-benzo [c] carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H- g, yield 70%).

¹ H-NMR:? 7.21 (m, 12H), 7.57 (m, 6H), 7.92

[ Preparation Example 24] Core 24  synthesis

(53.1 g, 168.8 mmol) was used in place of 11-bromo-7H-benzo [c] g, yield 64%).

¹ H-NMR:? 7.11 (m, 11H), 7.37 (d, IH), 7.62 (m, 6H), 7.92 (d, 2H), 8.31

[ Synthetic example  1] Compound 1 of  synthesis

(5.00 g, 10.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.0 mmol) and Pd ₂ (dba) ₃ (0.27 g, 0.3 mmol _{), (t-Bu) 3} P (0.4 g, 2.0 mmol), sodium tert-butoxide (NaOBu-t) (1.92 g, 20.0 mmol) is put into a 100 ml toluene (PhMe) was stirred at 110 ℃ for 12 hours . After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound (6.21 g, yield 85%) was obtained by column chromatography.

Mass: [(M + H) < ⁺ & gt ^; ]: 732

[ Synthetic example  2] Compound 6 of  synthesis

4-yl) -6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5- (6.61 g, yield 82%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 808

[ Synthetic example  3] Compound 9 of  synthesis

2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl- , The target compound (6.46 g, yield 80%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 809

[ Synthetic example  4] Compound Thirteen  synthesis

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5- (5.49 g, yield 78%).

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Synthetic example  5] Compound 17  synthesis

The same procedure as in Synthesis Example 1 was carried out except that 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5- To obtain the desired compound (6.48 g, yield 83%).

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  6] compound Fifteen  synthesis

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.16 g, 10.00 mmol) was used in place of 2-chloro-4,6-diphenyl- , The target compound (6.32 g, yield 81%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  7] Compound 74 of  synthesis

Using Core 2 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- The procedure of Synthesis Example 1 was repeated to obtain the desired compound (5.77 g, yield 79%).

Mass: [(M + H) < ⁺ & gt ^; ]: 731

[ Synthetic example  8] compound 77 of  synthesis

Core 1 and Core 2 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- The target compound (5.81 g, yield 72%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 809

[ Synthetic example  9] compound 83 of  synthesis

Core 1 and Core 2 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (6.54 g, yield 74%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 885

[ Synthetic example  10] compound 86  synthesis

Core 2 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used in place of Core 1 and 2-chloro-4,6-diphenyl- (5.35 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  11] compound 93  synthesis

Core 2 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (6.09 g, yield 78%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]:

[ Synthetic example  12] compound 94 of  synthesis

Core 2 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6-diphenyl- (6.36 g, yield 77%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the starting material (3.66 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 832

[ Synthetic example  13] Compound 25 of  synthesis

The procedure of Synthesis Example 1 was repeated except that Core 3 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (6.21 g, yield 88%).

Mass: [(M + H) < ⁺ & gt ^; ]: 706

[ Synthetic example  14] Compound 32  synthesis

Core 1 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (6.63 g, yield 85%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  15] Compound 33 of  synthesis

Core 3 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used in place of Core 1 and 2-chloro-4,6- -triazine (3.88 g, 10.00 mmol), the target compound (6.48 g, yield 83%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 782

[ Synthetic example  16] compound 37  synthesis

Excluding the use of Core 3 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (5.56 g, yield 82%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 679

[ Synthetic example  17] Compound 41 of  synthesis

Core 3 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (6.71 g, yield 89%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  18] compound 39 of  synthesis

Core 1 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The procedure of Synthesis Example 1 was repeated except that chloroquinazoline (3.16 g, 10.00 mmol) was used to obtain the desired compound (6.33 g, yield 84%).

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  19] Compound 99  synthesis

Using Core 4 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (5.07 g, yield 72%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Synthetic example  20] compound 101's  synthesis

Core 4 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (6.01 g, yield 77%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 782

[ Synthetic example  21] Compound 107  synthesis

Core 4 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (6.34 g, yield 74%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 859

[ Synthetic example  22] compound 110's  synthesis

Core 4 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.46 g, yield 75%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 729

[ Synthetic example  23] Compound 117's  synthesis

Core 4 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.96 g, yield 79%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  24] Compound 118  synthesis

Core 4 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used in place of Core 1 and 2-chloro-4,6- (3.66 g, 10.00 mmol), the target compound (5.79 g, yield 72%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 805

[ Synthetic example  25] Compound 49 of  synthesis

The procedure of Synthesis Example 1 was repeated, except that Core 5 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (6.13 g, yield 85%).

Mass: [(M + H) < ⁺ & gt ^; ]: 722

[ Synthetic example  26] compound 55  synthesis

Core 5 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (6.62 g, yield 83%) was obtained in the same manner as in Synthesis Example 1, except that chloro-6-phenylpyrimidine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 797

[ Synthetic example  27] Compound 57 of  synthesis

Core 5 (5.00 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine and 2- (3-bromophenyl) -triazine (3.88 g, 10.00 mmol), the target compound (6.70 g, yield 84%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 798

[ Synthetic example  28] Compound 61 of  synthesis

Except that Core 5 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (5.69 g, yield 82%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 695

[ Synthetic example  29] Compound 65  synthesis

Core 5 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- , The target compound (6.62 g, yield 86%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  30] Compound 63  synthesis

Core 5 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (6.70 g, yield 87%) was obtained by following the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  31] Compound 123  synthesis

Using Core 6 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (5.19 g, yield 72%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 721

[ Synthetic example  32] compound 125  synthesis

Core 1 and Core 6 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (5.98 g, yield 75%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 798

[ Synthetic example  33] Compound 131  synthesis

Core 1 and Core 6 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (6.37 g, yield 73%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 875

[ Synthetic example  34] Compound 134 of  synthesis

Core 6 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.51 g, yield 74%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 745

[ Synthetic example  35] Compound 141 of  synthesis

Core 6 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (6.08 g, yield 79%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  36] Compound 142  synthesis

Core 6 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6-diphenyl- (6.36 g, yield 77%) was obtained by following the same procedure as in Synthesis Example 1, except that the compound (3.66 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 822

[ Synthetic example  37] Compound 145's  synthesis

The procedure of Synthesis Example 1 was repeated except that Core 7 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (5.63 g, yield 77%).

Mass: [(M + H) < ⁺ & gt ^; ]: 732

[ Synthetic example  38] Compound 150  synthesis

Core 7 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6- The target compound (5.97 g, yield 74%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 808

[ Synthetic example  39] Compound 153's  synthesis

Except that Core 7 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used instead of Core 1 and 2-chloro-4,6- -triazine (3.88 g, 10.00 mmol), the target compound (5.81 g, yield 72%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 809

[ Synthetic example  40] Compound 157 of  synthesis

Except that Core 7 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (5.49 g, yield 78%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Synthetic example  41] Compound 161  synthesis

Core 3 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.62 g, yield 72%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  42] Compound Of 159  synthesis

Core 1 and Core 7 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (5.77 g, yield 74%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  43] Compound 219  synthesis

Using Core 8 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (5.11 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 731

[ Synthetic example  44] Compound 221  synthesis

Core 5 and 2 - ([1,1'-biphenyl] -4-yl) -4- (2-chloro-4,6-diphenyl- The target compound (5.73 g, yield 71%) was obtained in the same manner as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 809

[ Synthetic example  45] Compound 227  synthesis

Core 5 and 2 - ([1,1'-biphenyl] -4-yl) -4- (2-chloro-4,6-diphenyl- (6.09 g, yield 69%) was obtained in the same manner as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 885

[ Synthetic example  46] Compound 230  synthesis

Core 8 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.13 g, yield 68%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  47] Compound 237  synthesis

Core 8 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.62 g, yield 72%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  48] Compound 238  synthesis

Core 8 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6- (5.66 g, yield 69%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the starting material (3.66 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 832

[ Synthetic example  49] Compound 169  synthesis

The procedure of Synthesis Example 1 was repeated except that Core 9 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (5.43 g, yield 77%).

Mass: [(M + H) < ⁺ & gt ^; ]: 706

[ Synthetic example  50] Compound 176  synthesis

Core 1 (2.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- The target compound (5.70 g, yield 73%) was obtained by following the same procedure as in Synthesis Example 1 except that chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  51] Compound 177  synthesis

Core 9 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used in place of Core 1 and 2-chloro-4,6- -triazine (3.88 g, 10.00 mmol), the target compound (5.62 g, yield 72%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 782

[ Synthetic example  52] Compound 181  synthesis

Except that Core 9 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (5.36 g, yield 79%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 679

[ Synthetic example  53] Compound 185  synthesis

Core 9 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used in place of Core 1 and 2-chloro-4,6-diphenyl- (5.28 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  54] Compound 183  synthesis

Core 1 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (5.51 g, yield 73%) was obtained by following the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  55] Compound 242  synthesis

Using Core 10 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (5.07 g, yield 72%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Synthetic example  56] compound 245  synthesis

Core 1 and Core 10 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- The target compound (5.23 g, yield 67%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 782

[ Synthetic example  57] Compound 251  synthesis

Core 1 and Core 10 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (5.66 g, yield 66%) was obtained in the same manner as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 859

[ Synthetic example  58] Compound 254  synthesis

Core 10 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used in place of Core 1 and 2-chloro-4,6-diphenyl- (5.02 g, yield 69%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 729

[ Synthetic example  59] Compound 261  synthesis

Core 10 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.68 g, yield 62%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  60] Compound 262  synthesis

Core 10 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6- (3.66 g, 10.00 mmol), the target compound (5.07 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 805

[ Synthetic example  61] Compound 193's  synthesis

The procedure of Synthesis Example 1 was repeated except that Core 11 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (5.34 g, yield 74%).

Mass: [(M + H) < ⁺ & gt ^; ]: 722

[ Synthetic example  62] Compound 199  synthesis

Core 1 and Core 11 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (5.89 g, yield 74%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenylpyrimidine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 797

[ Synthetic example  63] compound Of 201  synthesis

Core 1 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5 -triazine (3.88 g, 10.00 mmol) was used in place of the compound obtained in Preparation Example 1 to obtain the desired compound (5.74 g, yield 72%).

Mass: [(M + H) < ⁺ & gt ^; ]: 798

[ Synthetic example  64] Compound 205's  synthesis

Excluding the use of Core 11 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (4.86 g, yield 70%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 695

[ Synthetic example  65] compound 209's  synthesis

Core 11 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- The procedure of Synthesis Example 1 was repeated to obtain the desired compound (5.47 g, yield 71%).

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  66] Compound Of 207  synthesis

Core 1 and Core 11 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (5.62 g, yield 73%) was obtained by following the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  67] Compound 267  synthesis

Using Core 12 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- The target compound (4.97 g, yield 69%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 721

[ Synthetic example  68] Compound 269 of  synthesis

Core 1 and Core 2 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (5.26 g, yield 66%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 798

[ Synthetic example  69] Compound 275  synthesis

Core 1 and Core 2 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (5.59 g, yield 64%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 875

[ Synthetic example  70] Compound 278  synthesis

Core 12 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.06 g, yield 68%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 745

[ Synthetic example  71] Compound 285  synthesis

Except that Core 12 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.85 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  72] Compound 286  synthesis

Core 2 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used in place of Core 1 and 2-chloro-4,6-diphenyl- (5.41 g, yield 66%) was obtained by following the same procedure as in Synthesis Example 1, except that the compound (3.66 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 822

[ Synthetic example  73] Compound 433  synthesis

The procedure of Synthesis Example 1 was repeated except that Core 13 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (4.24 g, yield 58%).

Mass: [(M + H) < ⁺ & gt ^; ]: 732

[ Synthetic example  74] Compound 438  synthesis

Core 1 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6- The target compound (4.76 g, yield 59%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 808

[ Synthetic example  75] Compound 441  synthesis

Core 13 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5 -triazine (3.88 g, 10.00 mmol), the target compound (4.68 g, yield: 58%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 809

[ Synthetic example  76] Compound 445  synthesis

Except that Core 13 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (3.73 g, yield 53%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Synthetic example  77] Compound 449  synthesis

Core 13 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used in place of Core 1 and 2-chloro-4,6-diphenyl- (4.29 g, yield 55%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  78] Compound 447  synthesis

Core 1 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (4.45 g, yield 57%) was obtained by following the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  79] compound 506  synthesis

Using Core 14 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- The procedure of Synthesis Example 1 was repeated to obtain the desired compound (3.72 g, yield 51%).

Mass: [(M + H) < ⁺ & gt ^; ]: 731

[ Synthetic example  80] Compound 509's  synthesis

4-yl) -4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was added to a solution of Core 14 (5.00 g, 10.00 mmol) (4.28 g, yield 53%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 809

[ Synthetic example  81] Compound 515  synthesis

Core 1 (2.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (4.77 g, yield 54%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 885

[ Synthetic example  82] Compound 518  synthesis

Core 14 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6- diphenyl- (4.15 g, yield 55%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  83] Compound 525  synthesis

Except that Core 14 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.06 g, yield 52%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  84] Compound 526  synthesis

Core 14 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.66 g, 10.00 mmol), the target compound (4.15 g, yield 50%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 832

[ Synthetic example  85] Compound 457  synthesis

The procedure of Synthesis Example 1 was repeated, except that Core 15 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (4.16 g, yield 59%).

Mass: [(M + H) < ⁺ & gt ^; ]: 706

[ Synthetic example  86] Compound 464  synthesis

Core 1 and Core 15 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (4.06 g, yield 52%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  87] compound 465  synthesis

Except that Core 15 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5 -triazine (3.88 g, 10.00 mmol) was used in place of the compound obtained in Preparation Example 1 (4.53 g, yield 58%).

Mass: [(M + H) < ⁺ & gt ^; ]: 782

[ Synthetic example  88] compound 469  synthesis

Except that Core 15 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (3.87 g, yield 57%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 679

[ Synthetic example  89] Compound 473 of  synthesis

Core 15 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.00 g, yield 53%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  90] Compound 471  synthesis

Core 1 and Core 15 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (4.15 g, yield 55%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  91] Compound 531  synthesis

Using Core 16 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- The procedure of Synthesis Example 1 was repeated to obtain the desired compound (3.52 g, yield 50%).

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Synthetic example  92] Compound 533  synthesis

Core 1 and Core 16 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (3.83 g, yield 49%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 782

[ Synthetic example  93] Compound 539  synthesis

Core 1 and Core 16 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (4.54 g, yield 53%) was obtained in the same manner as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 859

[ Synthetic example  94] Compound 542  synthesis

Core 16 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.86 g, yield 53%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 729

[ Synthetic example  95] compound 549  synthesis

Core 16 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.62 g, yield 48%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  96] Compound 550's  synthesis

Core 16 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.10 g, yield 51%) was obtained by following the same procedure as in Synthesis Example 1, except that the compound (3.66 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 805

[ Synthetic example  97] Compound 481  synthesis

The procedure of Synthesis Example 1 was repeated except that Core 17 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (4.25 g, yield 59%).

Mass: [(M + H) < ⁺ & gt ^; ]: 722

[ Synthetic example  98] Compound 486  synthesis

Core 1 and Core 17 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6- (4.62 g, yield 58%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 797

[ Synthetic example  99] compound Of 489  synthesis

Except that Core 17 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used in place of Core 1 and 2-chloro-4,6- -triazine (3.88 g, 10.00 mmol), the target compound (4.38 g, yield 55%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 798

[ Synthetic example  100] compound Of 493  synthesis

Except that Core 17 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.61 g, yield 52%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 695

[ Synthetic example  101] Compound 497  synthesis

Core 17 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.08 g, yield 53%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  102] Compound 495  synthesis

Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used instead of Core 17 (5.00 g, 10.00 mmol) and 4- (1,1'-biphenyl- The target compound (4.39 g, yield 57%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  103] Compound 554  synthesis

Using Core 18 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (3.53 g, yield 49%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 721

[ Synthetic example  104] Compound 557  synthesis

Core 1 and Core 18 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- The target compound (3.75 g, yield 47%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 798

[ Synthetic example  105] Compound 563  synthesis

Core 1 and Core 18 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (3.84 g, yield 44%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 875

[ Synthetic example  106] Compound 566  synthesis

Core 18 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.72 g, yield 50%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 745

[ Synthetic example  107] Compound 573  synthesis

Core 18 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.23 g, yield 42%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  108] Compound 574  synthesis

Core 18 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.66 g, yield: 48%) was obtained in the same manner as in Synthesis Example 1, except that the compound (3.66 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 822

[ Synthetic example  109] Compound 289 of  synthesis

The procedure of Synthesis Example 1 was repeated except that Core 19 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (5.05 g, yield 69%).

Mass: [(M + H) < ⁺ & gt ^; ]: 732

[ Synthetic example  110] compound 294  synthesis

Core 1 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6- The target compound (5.32 g, yield 66%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 808

[ Synthetic example  111] compound 297  synthesis

Core 19 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used in place of Core 1 and 2-chloro-4,6- -triazine (3.88 g, 10.00 mmol), the target compound (5.89 g, yield 73%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 809

[ Synthetic example  112] Compound 301's  synthesis

Except that Core 19 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (4.86 g, yield 69%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Synthetic example  113] Compound 305  synthesis

Core 19 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.46 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  114] Compound 303  synthesis

Core 1 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (5.31 g, yield 68%) was obtained by following the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  115] Compound 362  synthesis

Core 20 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- , The target compound (4.45 g, yield: 61%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 731

[ Synthetic example  116] Compound 365  synthesis

Except that Core 20 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- The target compound (4.84 g, yield 60%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 809

[ Synthetic example  117] compound 371  synthesis

Except that Core 20 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (5.12 g, yield 58%) was obtained in the same manner as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 885

[ Synthetic example  118] Compound 374  synthesis

Core 20 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.68 g, yield 62%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  119] Compound 381  synthesis

Core 20 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (5.15 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  120] Compound 382  synthesis

Core 20 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6- (3.63 g, 10.00 mmol) was used in place of the compound obtained in Preparation Example 1 to obtain the desired compound (5.23 g, yield 63%).

Mass: [(M + H) < ⁺ & gt ^; ]: 832

[ Synthetic example  121] Compound Of 313  synthesis

The procedure of Synthesis Example 1 was repeated except that Core 21 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (4.79 g, yield 68%).

Mass: [(M + H) < ⁺ & gt ^; ]: 706

[ Synthetic example  122] Compound 318  synthesis

Core 1 and Core 21 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6- The target compound (5.31 g, yield 68%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 781

[ Synthetic example  123] compound 321  synthesis

Except that Core 21 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5 -triazine (3.88 g, 10.00 mmol), the target compound (4.84 g, yield 62%) was obtained.

Mass: [(M + H) < ⁺ & gt ^; ]: 782

[ Synthetic example  124] Compound 325  synthesis

Except that Core 21 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (4.48 g, yield 66%) was obtained in the same manner as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 679

[ Synthetic example  125] compound 329  synthesis

Except that Core 21 (2.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.52 g, yield 60%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  126] compound 327  synthesis

Core 1 and Core 21 (5.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The target compound (5.20 g, yield 69%) was obtained by following the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  127] compound 386  synthesis

Using Core 22 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (4.30 g, yield 61%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Synthetic example  128] Compound 389  synthesis

Except that Core 22 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (4.53 g, yield 58%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 782

[ Synthetic example  129] Compound 395  synthesis

Except that Core 22 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (4.97 g, yield 58%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 859

[ Synthetic example  130] compound 398  synthesis

Core 22 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.51 g, yield 62%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 729

[ Synthetic example  131] compound 405  synthesis

(3.00 g, 10.00 mmol) and Core 22 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline in place of Core 1 and 2-chloro-4,6-diphenyl- (4.98 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 755

[ Synthetic example  132] compound 406  synthesis

Core 22 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used in place of Core 1 and 2-chloro-4,6- (4.66 g, yield 60%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the starting material (3.66 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 805

[ Synthetic example  133] compound 337  synthesis

The procedure of Synthesis Example 1 was repeated, except that Core 23 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the desired compound (4.47 g, yield 62%).

Mass: [(M + H) < ⁺ & gt ^; ]: 722

[ Synthetic example  134] Compound 342  synthesis

Core (1.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6- The target compound (5.02 g, yield 63%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 797

[ Synthetic example  135] compound 345  synthesis

Core 23 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5 -triazine (3.88 g, 10.00 mmol) was used in place of the compound obtained in Synthesis Example 1 to obtain the desired compound (5.26 g, yield 63%).

Mass: [(M + H) < ⁺ & gt ^; ]: 798

[ Synthetic example  136] Compound 349  synthesis

Except that Core 23 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (4.16 g, yield 60%) was obtained by the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 695

[ Synthetic example  137] Compound Of 353  synthesis

Core 23 (5.00 g, 10.00 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.70 g, yield: 61%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  138] Compound 351  synthesis

Core 1 (2.00 g, 10.00 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- The title compound (4.54 g, yield 59%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloroquinazoline (3.16 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  139] Compound 410  synthesis

Using Core 24 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- The procedure of Synthesis Example 1 was repeated to obtain the desired compound (4.18 g, yield 58%).

Mass: [(M + H) < ⁺ & gt ^; ]: 721

[ Synthetic example  140] Compound 413  synthesis

Except that Core 24 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (4.38 g, yield 55%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 798

[ Synthetic example  141] Compound 419  synthesis

Except that Core 24 (5.00 g, 10.00 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (4.98 g, yield: 57%) was obtained in the same manner as in Synthesis Example 1, except that 3-bromophenyl-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) ≪ / RTI >

Mass: [(M + H) < ⁺ & gt ^; ]: 875

[ Synthetic example  142] Compound 422  synthesis

Core 24 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo [h] quinazoline (2.90 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.72 g, yield 50%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

Mass: [(M + H) < ⁺ & gt ^; ]: 745

[ Synthetic example  143] Compound 429  synthesis

Core 24 (5.00 g, 10.00 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (3.61 g, 10.00 mmol) were used instead of Core 1 and 2-chloro-4,6-diphenyl- (3.93 g, yield 51%) was obtained by carrying out the same procedure as in Synthesis Example 1. [

Mass: [(M + H) < ⁺ & gt ^; ]: 771

[ Synthetic example  144] compound 430  synthesis

Core 24 (5.00 g, 10.00 mmol) and 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used instead of Core 1 and 2-chloro-4,6-diphenyl- (4.51 g, yield 55%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the starting material (3.66 g, 10.00 mmol) was used.

Mass: [(M + H) < ⁺ & gt ^; ]: 822

[ Synthetic example  145] Compound 27  synthesis

Core 3 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) were used in place of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- , The target compound (4.23 g, yield 60%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) < ⁺ & gt ^; ]: 705

[ Example  1 to 72] Red organic Field  Fabrication of light emitting device

The compounds 13, 15, 17, 37, 39, 41, 61, 63, 65, 86, 93, 94, 110, 117, 118, 134, 141, 142, 157, 159, 161, 181 , 183, 185, 205, 207, 209, 230, 237, 238, 254, 261, 262, 278, 285, 286, 301, 303, 305, 325, 327, 329, 349, 351, 353, 374, 381 , 382, 398, 405, 406, 422, 429, 430, 445, 447, 469, 471, 473, 493, 495, 497, 518, 525, 526, 542, 549, 550, 566, 573, The red organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with 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.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% Each compound of Table 2 + 10% (piq) ₂ Ir (acac) (300 nm) / 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] Red organic Field  Fabrication of light emitting device

A red organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of Compound 13 as a luminescent host material in forming the light emitting layer.

[ Comparative Example  2] Red organic Field  Fabrication of light emitting device

A red organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound A was used instead of Compound 13 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, (piq) ₂ Ir (acac), BCP, CBP and Compound A used in Examples 1 to 72 and Comparative Examples 1 and 2 are as follows.

[ Evaluation example  One]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the red organic electroluminescent devices manufactured in Examples 1 to 72 and Comparative Examples 1 and 2, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 1 Compound 13 4.7 11.9 Example 2 Compound 15 4.7 11.6 Example 3 Compound 17 4.7 12.4 Example 4 Compound 37 4.7 13.2 Example 5 Compound 39 4.8 12.5 Example 6 Compound 41 4.8 12.6 Example 7 Compound 61 4.8 12.3 Example 8 Compound 63 4.7 12.2 Example 9 Compound 65 4.7 12.5 Example 10 Compound 86 4.8 11.7 Example 11 Compound 93 4.8 11.6 Example 12 Compound 94 4.7 11.5 Example 13 Compound 110 4.7 12.4 Example 14 Compound 117 4.8 12.4 Example 15 Compound 118 4.8 12.3 Example 16 Compound 134 4.8 11.7 Example 17 Compound 141 4.8 12.3 Example 18 Compound 142 4.8 12.6 Example 19 Compound 157 4.8 12.6 Example 20 Compound 159 4.7 12.4 Example 21 Compound 161 4.7 11.2 Example 22 Compound 181 4.7 11.1 Example 23 Compound 183 4.7 11.3 Example 24 Compound 185 4.7 11.5 Example 25 Compound 205 4.8 12.3 Example 26 Compound 207 4.8 12.2 Example 27 Compound 209 4.8 12.2 Example 28 Compound 230 4.7 11.3 Example 29 Compound 237 4.7 11.4 Example 30 Compound 238 4.7 12.5 Example 31 Compound 254 4.8 12.4 Example 32 Compound 261 4.8 12.2 Example 33 Compound 262 4.7 11.7 Example 34 Compound 278 4.8 11.5 Example 35 Compound 285 4.7 12.4 Example 36 Compound 286 4.8 12.6 Example 37 Compound 301 4.7 12.4 Example 38 Compound 303 4.8 11.2 Example 39 Compound 305 4.7 11.5 Example 40 Compound 325 4.8 11.6 Example 41 Compound 327 4.8 12.6 Example 42 Compound 329 4.8 12.4 Example 43 Compound 349 4.8 12.4 Example 44 Compound 351 4.8 11.3 Example 45 Compound 353 4.7 12.5 Example 46 Compound 374 4.7 12.6 Example 47 Compound 381 4.8 12.7 Example 48 Compound 382 4.8 11.8 Example 49 Compound 398 4.8 12.9 Example 50 Compound 405 4.7 12.9 Example 51 Compound 406 4.7 12.7 Example 52 Compound 422 4.7 12.7 Example 53 Compound 429 4.8 11.6 Example 54 Compound 430 4.8 11.4 Example 55 Compound 445 4.8 11.3 Example 56 Compound 447 4.8 12.2 Example 57 Compound 449 4.8 12.3 Example 58 Compound 469 4.8 12.4 Example 59 Compound 471 4.9 12.5 Example 60 Compound 473 4.8 12.6 Example 61 Compound 493 4.7 11.3 Example 62 Compound 495 4.8 11.2 Example 63 Compound 497 4.7 11.5 Example 64 Compound 518 4.8 11.7 Example 65 Compound 525 4.8 11.8 Example 66 Compound 526 4.8 12.5 Example 67 Compound 542 4.7 12.4 Example 68 Compound 549 4.8 12.2 Example 69 Compound 550 4.7 12.3 Example 70 Compound 566 4.8 12.5 Example 71 Compound 573 4.8 11.7 Example 72 Compound 574 4.8 11.8 Comparative Example 1 CBP 5.25 8.2 Comparative Example 2 Compound A 5.12 9.7

As shown in Table 2, the red organic electroluminescent devices (Examples 1 to 72) using the compound according to the present invention in the light emitting layer were red organic electroluminescent devices (Comparative Example 1 or 2) using CBP or Compound A as the light emitting layer, Which is superior in current efficiency and driving voltage.

Further, for each red organic electroluminescent device manufactured in Examples 1, 5, 7, 8, 10, 13, 19, 22, 25, 28, 31 and 34 and Comparative Examples 1 and 2, the lifetime The time required for the luminance to decrease to 90%) was measured. The results are shown in Table 3 below.

Sample Host Life (T90) Example 1 Compound 13 80 Example 5 Compound 39 85 Example 7 Compound 61 90 Example 8 Compound 63 75 Example 10 Compound 86 70 Example 13 Compound 110 85 Example 19 Compound 157 65 Example 22 Compound 181 70 Example 25 Compound 205 85 Example 28 Compound 230 80 Example 31 Compound 254 65 Example 34 Compound 278 60 Comparative Example 1 CBP 20 Comparative Example 2 Compound A 40

As shown in Table 3, the red organic electroluminescent devices (Examples 1, 5, 7, 8, 10, 13, 19, 22, 25, 28, 31 and 34) using the compound according to the present invention in the light- (Comparative Example 1 or 2) using CBP or Compound A as a light emitting layer.

[ Example  73 to 145] Green organic Field  Fabrication of light emitting device

The compounds 1, 6, 9, 25, 27, 32, 33, 49, 55, 57, 74, 77, 83, 99, 101, 107, 123, 125, 131, 145, 150, 153 , 169, 176, 177, 193, 199, 201, 219, 221, 227, 242, 245, 251, 267, 269, 275, 289, 294, 297, 313, 318, 321, 337, 342, 345, 362 , 365, 371, 386, 389, 395, 410, 413, 419, 433, 438, 441, 457, 464, 465, 481, 486, 489, 506, 509, 515, 531, 533, 539, 554, 557 , 563 were purified by high purity sublimation by a conventionally known method, and then a green organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with 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.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% Each compound of Table 4 + 10% Ir (ppy) ₃ (300 nm) / 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  3] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 73, except that CBP was used instead of Compound 1 as a luminescent host material in forming the light emitting layer.

[ Comparative Example  4] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 73, except that Compound B was used instead of Compound 1 as a luminescent host material in forming the light emitting layer.

[ Comparative Example  5] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 73, except that Compound C was used instead of Compound 1 as a luminescent host material in forming the light emitting layer.

The structures of Ir (ppy) ₃ , Compound B and Compound C are as follows.

[ Evaluation example  2]

Current efficiency and emission peak at current density of 10 mA / cm < 2 > were measured for each of the green organic electroluminescent devices manufactured in Examples 73 to 145 and Comparative Examples 3 to 5, Respectively.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 73 Compound 1 6.1 516 42.9 Example 74 Compound 6 6.1 517 42.8 Example 75 Compound 9 6.1 518 42.7 Example 76 Compound 25 6.1 518 43.8 Example 77 Compound 27 6.2 517 43.5 Example 78 Compound 32 6.1 517 43.3 Example 79 Compound 33 6.1 516 43.6 Example 80 Compound 49 6.2 517 42.3 Example 81 Compound 55 6.2 518 42.5 Example 82 Compound 57 6.2 518 42.6 Example 83 Compound 74 6.2 517 43.3 Example 84 Compound 77 6.1 518 43.4 Example 85 Compound 83 6.1 517 43.7 Example 86 Compound 99 6.1 518 42.3 Example 87 Compound 101 6.2 515 42.3 Example 88 Compound 107 6.2 516 42.4 Example 89 Compound 123 6.2 516 42.7 Example 90 Compound 125 6.2 517 42.5 Example 91 Compound 131 6.2 518 43.6 Example 92 Compound 145 6.1 518 43.7 Example 93 Compound 150 6.1 517 43.6 Example 94 Compound 153 6.1 516 43.4 Example 95 Compound 169 6.1 517 43.3 Example 96 Compound 176 6.1 518 42.5 Example 97 Compound 177 6.2 518 42.6 Example 98 Compound 193 6.2 517 42.4 Example 99 Compound 199 6.2 518 43.2 Example 100 Compound 201 6.2 517 43.4 Example 101 Compound 219 6.1 518 42.6 Example 102 Compound 221 6.2 515 43.7 Example 103 Compound 227 6.2 516 42.5 Example 104 Compound 242 6.1 516 43.4 Example 105 Compound 245 6.2 517 42.3 Example 106 Compound 251 6.1 518 43.3 Example 107 Compound 267 6.2 518 42.4 Example 108 Compound 269 6.2 517 43.5 Example 109 Compound 275 6.1 516 42.6 Example 110 Compound 289 6.1 517 43.6 Example 111 Compound 294 6.1 518 43.7 Example 112 Compound 297 6.1 518 43.7 Example 113 Synthesis of Compound 313 6.1 517 43.6 Example 114 Compound 318 6.2 518 42.6 Example 115 Compound 321 6.2 517 42.5 Example 116 Compound 337 6.2 518 42.5 Example 117 Compound 342 6.2 515 42.3 Example 118 Compound 345 6.2 516 42.4 Example 119 Compound 362 6.1 516 43.5 Example 120 Compound 365 6.1 517 43.6 Example 121 Compound 371 6.1 518 43.6 Example 122 Compound 386 6.1 518 43.4 Example 123 Compound 389 6.2 517 43.2 Example 124 Compound 395 6.2 516 42.2 Example 125 Compound 410 6.2 517 42.1 Example 126 Compound 413 6.2 518 42.1 Example 127 Compound 419 6.1 518 42.0 Example 128 Compound 433 6.1 517 42.0 Example 129 Compound 438 6.1 518 43.9 Example 130 Compound 441 6.2 517 43.9 Example 131 Compound 457 6.2 518 43.8 Example 132 Compound 464 6.1 515 42.6 Example 133 Compound 465 6.1 516 42.6 Example 134 Compound 481 6.2 516 43.7 Example 135 Compound 486 6.2 517 43.7 Example 136 Compound 489 6.2 518 43.2 Example 137 Compound 506 6.1 518 43.2 Example 138 Compound 509 6.1 517 42.3 Example 139 Compound 515 6.1 516 42.8 Example 140 Compound 531 6.2 517 42.9 Example 141 Compound 533 6.2 518 43.7 Example 142 [ Compound 539 6.2 518 43.3 Example 143 Compound 554 6.2 517 43.5 Example 144 Compound 557 6.1 518 42.9 Example 145 Compound 563 6.1 517 42.3 Comparative Example 3 CBP 6.93 516 38.2 Comparative Example 4 Compound B 6.8 515 40.2 Comparative Example 5 Compound C 6.5 516 39.6

As shown in Table 4, the green organic electroluminescent devices (Examples 73 to 145) using the compound according to the present invention in the light emitting layer were the same as the green organic electroluminescent devices using the CBP, Compound B or Compound C in the light emitting layer , 4, or 5), the current efficiency and the driving voltage were superior to each other.

The green organic electroluminescent devices fabricated in Examples 73, 75, 76, 79, 85, 89, 91, 93, 94, 96, 97 and 99, The time required for the luminance to decrease to 90%) was measured. The results are shown in Table 5 below.

Sample Host Lifetime (T95) Example 73 Compound 1 25 Example 75 Compound 9 30 Example 76 Compound 25 35 Example 79 Compound 49 30 Example 85 Compound 99 40 Example 89 Compound 125 25 Example 91 Compound 145 20 Example 93 Compound 153 30 Example 94 Compound 169 25 Example 96 Compound 177 40 Example 97 Compound 193 30 Example 99 Compound 201 35 Comparative Example 3 CBP  10 Comparative Example 4 Compound B 15 Comparative Example 5 Compound C 15

The green organic electroluminescent devices (Examples 73, 75, 76, 79, 85, 89, 91, 93, 94, 96, 97, and 99) using the compound according to the present invention in the light emitting layer (Comparative Example 3, 4 or 5) in which CBP, Compound B or Compound C was used for the light emitting layer.

Claims (9)

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

In Formula 1,
L ₁ and L ₂ are the same or different and are each independently 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 nucleus atoms,
Plural R ₁ are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group and C ₂ ~ C Or an alkynyl group having 1 to ₄₀ carbon atoms, or may be bonded to adjacent groups to form a condensed ring, but at least one condensed ring is formed,
B is a substituent represented by the following formula (2)
(2)

In Formula 2,
* Represents a moiety bonded to Formula 1,
X is selected from the group consisting of C (R ₃ ) (R ₄ ), O and S,
Ar ₁ and Ar ₂ are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ alkynyl group of C _40, C 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 ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C the group of boron ₆₀ aryl, C ₆ ~ C ₆₀ aryl phosphine group, is selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of,
m is an integer of 0 to 3,
R ₂ to R ₄ are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ alkynyl group of C _40, C 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 ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group of ₆₀ arylboronic, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of or, or adjacent groups bonded fused to the A ring can be formed,
Wherein L _1, and arylene group of L ₂ and a heteroarylene group, an alkyl group of said Ar ₁ and Ar _2, R ₁ to R _4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, 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 C ₆ -C An arylamine group having 1 to ₆₀ carbon atoms, and when the substituent is plural, they may be the same or different from each other. The method according to claim 1,
Wherein Ar ₁ and Ar ₂ are the same or different and each independently represents 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 a C ₆ to C ₆₀ An arylamine group, and an arylamine group. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by at least one of the following formulas (3) to (5).
(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 3 to 5,
L ₁ , L ₂ , Ar ₁ , Ar ₂ , m and R ₂ are as defined in claim 1, respectively. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by at least one of the following formulas (6) to (8).
[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas (6) to (8)
L ₁ , L ₂ , Ar ₁ , Ar ₂ , m and R ₂ are as defined in claim 1, respectively. The method according to claim 1,
Wherein Ar < ₁ > is a substituent represented by the following formula (9).
[Chemical Formula 9]

In the above formula (9)
* Represents a moiety bonded to Formula 1,
Z ₁ to Z ₅ are the same or different and each independently N or C (R ₅ ), wherein when R ₅ is plural, they are the same or different,
R ₅ is hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of the A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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 An 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, a C ₆ to C ₆₀ An arylphosphine group, an arylphosphine oxide group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring,
Alkyl groups of the R _5, 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 a heavy hydrogen (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C _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 alkenyl group, C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, substituted with one or more substituents selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of And when the substituent is plural, they may be the same or different from each other. 6. The method of claim 5,
The substituent represented by the formula (9) is represented by any one of the following A-1 to A-15.

In the above A-1 to A-15,
R < ₅ > is as defined in claim 5,
p is an integer of 0 to 4,
R ₆ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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 An 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, a C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of, or by groups coupled to or adjacent to can form a fused ring, wherein R ₆ a plurality , They may be the same or different from each other,
Alkyl group of the R _6, 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 a heavy hydrogen (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C _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 alkenyl group, C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, substituted with one or more substituents selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of And when the substituent is plural, 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 6. 8. The method of claim 7,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. 9. The method of claim 8,
Wherein the organic compound layer containing the compound is a phosphorescent light-emitting layer.