KR20150133097A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound applied to an organic light emitting device. The organic light emitting compound: is represented by chemical formula 1; includes one or more substituted bodies represented by structural formula 1 or structural formula 2; and is capable of realizing an organic light emitting device having excellent luminous properties such as driving voltage, luminance, a long life and the like in the case of being applied as a phosphorescent host compound in a hole transporting functional layer or an emissive layer.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic light emitting compound, and more particularly, to an organic light emitting compound which is employed as a host compound or a hole transport material in an organic electroluminescent device, and an organic electroluminescent device .

The organic electroluminescent device can not only form an element on a transparent substrate but also can operate at a low voltage of 10 V or less as compared with a plasma display panel (Plasma Display Panel) or an inorganic electroluminescence (EL) display, It has the advantage of excellent color and has three colors of green, blue, and red. It has recently become a subject of interest as a next generation display device.

However, in order for such an organic electroluminescent device to exhibit such characteristics, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are materials forming an organic layer in a device, However, until now, stable and efficient development of an organic layer material for an organic electroluminescence element has not been sufficiently developed yet. Therefore, there is a continuing demand for development of new materials having low-voltage driving, high efficiency and long life.

In particular, conventional hole transport materials include copper phthalocyanine (CuPc), MTDATA, 4,4'-bis [N- (1-naphthyl) -N- phenylamino] biphenyl (NPB), N, N, N'-bis (3-methylphenyl) - (1,1'-biphenyl) -4,4'-diamine (TPD) has been known. However, Based compound having various substituents in order to improve it, but it still has a problem that it is not enough to satisfy efficiency and long life at the same time.

Further, the most important factor for determining the luminous efficiency in an organic light emitting device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, In particular, CBP is the most widely known phosphorescent host material, and an organic light emitting device using a BALq derivative as a host is known.

However, in the case of using a material such as BAlq or CBP as a host of a phosphorescent material, the organic electroluminescent device using the phosphorescent material has a higher current efficiency than the device using the fluorescent material, There is no great advantage in terms of power efficiency, and the life of the device can not be satisfactory. Thus, development of a more stable and high-performance host material is required.

Korean Patent Publication No. 10-2012-0131870

The present invention provides a novel organic electroluminescent compound which can be used for a light emitting layer, a hole injecting layer, and a hole transporting layer of an organic electroluminescent device to realize excellent luminescent characteristics, and an organic electroluminescent device including the same.

In order to solve the above problems, the present invention provides an organic electroluminescent compound having as a substituent the following structural formula 1 or structural formula 2 in a core skeleton represented by the following formula (1) and an organic electroluminescent device Lt; / RTI >

[Chemical Formula 1]

[Structural formula 1]

[Structural formula 2]

The specific structures and substituents of the organic luminescent compounds according to the above formulas (1) and (1) to (2) will be described later.

The organic luminescent compound according to the present invention has an excellent structure flatness and a high triplet state, which enables to realize a luminescent efficiency and a longevity characteristic which are higher than those of conventional phosphorescent host compounds and hole transport compounds, The light emitting device can be used for various display devices.

1 to 5 are cross-sectional views illustrating the structure of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described more specifically.

The present invention relates to a novel organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

Wherein X ₁ to X ₁₀ are each independently N or CR ₁ and X ₁₁ is a single bond or CR ₂ R ₃ , CR ₄ , NR ₅ , PR ₆ , SiR ₇ R ₈ , O and S, < / RTI >

Each of R ₁ to R ₈ is independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C1 to C30 arylthio group, An unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted C3 to C30 cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, an amino group, a thiol group, a cyano group, a hydroxyl group, a nitro group and a halogen group.

The adjacent substituents of R ₁ to R ₈ may be connected with each other to form a monocyclic or polycyclic ring of an alicyclic or aromatic group and the carbon atom of the monocyclic or aromatic monocyclic or polycyclic ring formed may be N, Lt; / RTI > may be substituted with any one or more heteroatoms selected from < RTI ID = 0.0 >

Each of R ₁ to R ₈ may further be substituted with at least one substituent, and the at least one substituent may be substituted with at least one substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, An alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, An alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms.

The organic electroluminescent compound of Formula 1 according to the present invention may be any one selected from the following Formulas 2 to 17:

In the above formulas (2) to (17), the definitions of X ₁ to X ₁₁ are as defined in the above formula (1).

Each of the substituents of X ₁ to X ₁₁ may be connected to adjacent substituents to form a monocyclic or polycyclic ring of an alicyclic or aromatic group, and the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be N , S and < RTI ID = 0.0 > O, < / RTI >

In addition, the present invention is characterized by having a substituent characteristic of the core skeleton as shown in the above formulas (2) to (17).

At least one of X ₂ to X ₆ in the formulas (1) to (17) is CR ₃ , and * -R ₃ is represented by the following structural formula (1) Has at least one substituent of the following structural formula 1 and has a very high molecular structure flatness and a high triplet energy, so that it can be used as a hole transport material.

[Structural formula 1]

In the structural formula 1,

L ₁ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which at least one unsubstituted or substituted unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms is fused.

n is an integer of 0 to 4, and when n is 2 or more, a plurality of L ₁ may be the same or different from each other.

Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 50 carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl substituted or unsubstituted aryl group having 5 to 50 carbon atoms, And a substituted or unsubstituted C2 to C50 heteroaryl group in which one or more ring-opened cycloalkyl having 3 to 30 carbon atoms is fused.

Ar ₁ and Ar ₂ may be bonded to each other or may be connected to adjacent substituents to form a monocyclic or polycyclic ring of an alicyclic or aromatic group. The carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be N, S and < RTI ID = 0.0 > O, < / RTI >

p is an integer of 0 to 3, and when p is 2 or more, a plurality of * - () may be the same or different from each other.

Further, L _1, Ar ₁ and Ar ₂ each may be further substituted with one or more substituents, the one or more substituents are deuterium, a cyano group, an alkyl group, a halogen group, a hydroxyl group, a nitro group, having 1 to 24 carbon atoms, A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms , An alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms.

In the formulas (1) to (17), at least one of X ₂ to X ₁₀ is CR ₃ , and * -R ₃ is [Structural Formula 2] Has at least one substituent of the following formula [2] and has a very high molecular structure flatness and a high triplet energy, so that it can be used as a phosphorescent host compound in a light emitting layer.

[Structural formula 2]

In the above formula 2,

L ₂ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which at least one unsubstituted or substituted unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms is fused.

m is an integer of 0 to 4, and when m is 2 or more, a plurality of L ₂ may be the same or different from each other.

And Ar ₃ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, And a substituted or unsubstituted C2 to C50 heteroaryl group in which at least one of 3 to 30 cycloalkyls is fused.

And q is an integer of 0 to 3, and when q is 2 or more, a plurality of Ar ₃ may be the same or different from each other, and the plurality of Ar ₃ and the substituent thereof may be linked to adjacent substituents to form alicyclic or aromatic groups And a carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S and O.

Each of L ₂ and Ar ₃ may be further substituted with one or more substituents. The substituent may be one or more substituents selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, An alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms.

In the present invention, examples of the substituents will be specifically described below, but the present invention is not limited thereto.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, A tert-butyl group, a tert-butyl group, a 2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.

In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably in the range of 1 to 30, which does not cause steric hindrance. Specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, a n-butoxy group, an isobutoxy group, a tert- , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n- , A benzyloxy group, a p-methylbenzyloxy group, and the like, but are not limited thereto.

In the present invention, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. [ Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluororanthrene group, but the scope of the present invention is not limited to these examples.

In the present invention, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofurancyl group, a phenanthroline group, An isothiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group and the like, but is not limited thereto.

In the present invention, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a ptert- Anthryloxy group, 2-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, Anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group and the like. Examples of the arylthioxy group include phenylthioxy group, 2- A 4-tert-butylphenyloxy group, and the like. Examples of the arylsulfoxy group include benzene sulfoxy group and p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, Methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo An octyl group, and the like, but are not limited thereto.

In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, But are not limited to, an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group and a triphenylamine group.

In the present invention, the silyl group is specifically exemplified by trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, But are not limited thereto.

In the present invention, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

In the present invention, the alkyloxy group in the alkylthio group and the alkyl group in the alkylsulfoxy group are the same as the aforementioned alkyl groups. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.

In the present invention, the "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, alkyl, cycloalkyl, , An arylsulfoxy group, an alkenyl group, a silyl group, a boron group, an alkylamine group, an aralkylamine group, an arylamine group, an aryl group, a fluorenyl group, a carbazole group and at least one of N, O and S atoms Substituted or unsubstituted with at least one substituent in the heterocyclic group.

In the present invention, the substituted arylene group means a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group. Anthracenyl group and the like are substituted with other substituents.

In the present invention, the substituted heteroarylene group includes a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and condensed heterocyclic groups, Such as a benzoquinoline group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzzcarbazole group, a dibenzothiophenyl group, a dibenzofurane group and the like are substituted with other substituents.

The organic luminescent compound according to the present invention represented by Formula 1 can be used as an organic material layer of an organic electroluminescent device due to its structural specificity and more specifically can be used as a hole transport material in a hole transport layer or a hole injection layer in an organic material layer. have.

Specific examples of the organic luminescent compound that can be employed as the hole transporting material represented by Formula 1 according to the present invention include, but are not limited to, the following compounds.

The organic luminescent compound according to the present invention represented by Formula 1 can be used as an organic material layer of an organic electroluminescent device due to its structural specificity and more specifically as a phosphorescent host compound in a luminescent layer.

Specific examples of the organic luminescent compound that can be employed as the phosphorescent host compound of the luminescent layer represented by Formula 1 according to the present invention include, but are not limited to, the following compounds.

An organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituents into the core structure having the above structure can be synthesized. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic electroluminescent device into the structure, a material meeting the requirements of each organic material layer is manufactured .

In particular, as described above, the organic luminescent compound represented by Formula 1 according to the present invention has a superior flat structure and a high triplet state as a result of introducing a substituent to the characteristic core structure. It is possible to realize an organic electroluminescent device exhibiting excellent characteristics in terms of efficiency, driving voltage and lifetime when the organic electroluminescent device is used in an organic material layer of the organic electroluminescent device.

The compound of the present invention can be applied to a device according to a conventional method of manufacturing an organic electroluminescent device.

The organic electroluminescent device according to one embodiment of the present invention may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic electroluminescent compound according to the present invention may be used for an organic material layer And can be manufactured using conventional device manufacturing methods and materials.

The organic material layer of the organic electroluminescent device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. However, it is not limited to this and may include a smaller number of organic layers.

Therefore, in the organic electroluminescent device of the present invention, the organic material layer may be a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously injecting and transporting holes, a layer simultaneously performing electron injection and electron transporting, One or more layers may be included, and at least one of the layers may include a compound represented by the above formula (1).

In particular, the organic luminescent compound according to the present invention may be contained in the hole transporting functional layer or the luminescent layer, and may be included as a host material in the luminescent layer.

In the case where the compound represented by Formula 1 is included as a host material in the light emitting layer, the light emitting layer may include at least one phosphorescent dopant. When the light emitting layer includes a host and a dopant, In the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host.

According to an embodiment of the present invention, the light emitting layer may further contain at least one dopant compound selected from the following [structural formulas 2] to [structural formula 8] in the host compound represented by the general formula [1] have.

[Structural formula 2]

[Structural Formula 3]

[Structural Formula 4]

[Structural Formula 5]

[Structural Formula 6]

[Structural Formula 7]

[Structural formula 8]

In the organic compound layer having such a multilayer structure, the compound represented by the formula (1) may be used in combination with a light emitting layer, a layer that simultaneously transports holes and holes, a layer that simultaneously transports holes and emits light, .

For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.

1 shows an organic electronic device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially laminated on a substrate 1 Structure is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, the light emitting layer 5, or the electron transporting layer 6.

2 shows the structure of an organic electronic device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5 and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, or the electron transporting layer 6.

3 illustrates the structure of an organic electronic device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially stacked on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.

4 illustrates the structure of an organic electronic device in which an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound represented by Formula 1 may be included in the light-emitting layer 5 or the electron-transporting layer 6.

5 illustrates the structure of an organic electronic device in which an anode 2, a light-emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1. As shown in Fig. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 5.

For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.

1 shows an organic electroluminescent device 1 in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially laminated on a substrate 1 Are illustrated. In this structure, the compound represented by the formula (1) may be included in the hole injection layer (3), the hole transport layer (4), the light emitting layer (5) or the electron transport layer (6).

2 shows a structure of an organic electroluminescent device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5 and a cathode 7 are sequentially laminated on a substrate 1 . In such a structure, the compound represented by the formula (1) may be included in the hole injection layer (3), the hole transport layer (4), or the electron transport layer (6).

3 illustrates the structure of an organic electroluminescent device in which an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by the formula (1) may be included in the hole transport layer (4), the light emitting layer (5), or the electron transport layer (6).

4 shows the structure of an organic electroluminescent device in which an anode 2, a light emitting layer 5, an electron transport layer 6 and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by the formula (1) may be included in the light-emitting layer (5) or the electron-transporting layer (6).

5 illustrates the structure of an organic electroluminescent device in which an anode 2, a light-emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. As shown in FIG. In such a structure, the compound represented by the formula (1) may be included in the luminescent layer (5).

For example, the organic electroluminescent device according to the present invention can be manufactured by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal oxide or a conductive metal oxide on the substrate, An anode is formed by depositing an alloy on the anode, and an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and then a substance usable as a cathode is deposited thereon.

In addition to such a method, an organic electroluminescent device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) metal oxides, ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) , Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

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

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

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

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazol-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and A benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, and the like.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable. Specific examples thereof include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex.

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

In addition, the organic electroluminescent compound according to the present invention can act on a principle similar to that applied to an organic electroluminescent device in an organic electronic device including an organic solar cell, an organophotoreceptor, an organic transistor and the like.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

Example  1: Synthesis of Compound 366

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

Phenylmethanamine (7.0 g, 0.066 mol) and ferric chloride (0.07 g, 0.0004 mol) were added to 2-nitroaniline (3.0 g, 0.022 mol) and the mixture was reacted at 120 ° C for 48 hours with stirring. After completion of the reaction, the reaction mixture was cooled to room temperature, and 50 mL of MC was added thereto, followed by stirring for 30 minutes, followed by filtration. The obtained solid was subjected to column purification (n-hexane: EA) to obtain 3.1 g (yield 80%) of Intermediate 1-1. (M / z = 194)

(2) Manufacturing example  2: Synthesis of intermediate 1-2

Potassium carbonate (2.8 g, 0.020 mol), Copper (0.1 g, 0.0020 mol), iodine copper (1.1 g, 0.020 mol) were added to intermediate 1-1 (2.0 g, 0.010 mol) , 0.006 mol) were dissolved in 70 mL of n-butyl ether and reacted under nitrogen for 48 hours with stirring. After completion of the reaction, the reaction mixture was cooled to room temperature, and subjected to column separation (n-hexane: EA) after separation of H ₂ O: MC layer to obtain 2.8 g (m / z = 407)

(3) Manufacturing example  3: Synthesis of intermediate 1-3

Intermediate 1-2 (4.0 g, 0.010 mol) was dissolved in a 30 mL ehter, cooled to -78 ° C, and 2.5 M BuLi (0.01 mL, 0.0005 mol) was dropwise added thereto, followed by stirring for 1 hour. The mixture was slowly warmed to room temperature and stirred for 4 hours. After completion of the reaction, the reaction mixture was extracted with 100 mL of water, and the organic layer was dried under reduced pressure. This was recrystallized from EtOH: Acetone to give intermediate 1-3 (2.7 g, 67%). (M / z = 407)

(4) Manufacturing example  4: Synthesis of intermediate 1-4

Intermediate 1-3 (4.0 g, 0.010 mol) was dissolved in 50 mL of concentrated H ₃ PO ₄ and stirred for 5 h. It was extracted with 100 mL of water and 100 mL of Ethyl Acetate, and the organic layer was dried under reduced pressure. This was recrystallized from 100 mL of EtOH to obtain intermediate 1-4 (2.8 g, 72%). (m / z = 389)

(5) Manufacturing example  5: Synthesis of intermediate 1-4 '

To a solution of bis (pinacolato) dibron (2.5 g, 0.010 mol), PdCl ₂ (dppf) (0.3 g, 0.0004 mol) and potassium acetate (2.2 g, 0.016 mol) in Intermediate 1-4 (3.0 g, 0.008 mol) , 4-dioxane (80 mL), and the mixture was reacted at 95 ° C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 2.5 g (yield 71%) of intermediate 1-4 '. (m / z = 436)

(6) Manufacturing example  6: Synthesis of intermediate 1-5

Pd (dba) ₂ (0.5 g, 0.00006 mol) and sodium-tert-butoxide (2.2 g, 0.022 mol) in 1,4-dibromobenzene (1.3 g, 0.006 mol) Was added 80 mL of Tol, and the mixture was reacted at 95 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and the product was separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 2.1 g (m / z = 465)

(7) Manufacturing example  7: Synthesis of intermediate 1-5 '

Intermediate 1-5 'was synthesized in the same manner as in Example 1 (5) except that bis (pinacolato) dibron (2.0 g, 0.008 mol) was added to Intermediate 1-5 (3.0 g, 0.006 mol) 2.2 g (71% yield) was obtained. (m / z = 512)

(8) Manufacturing example  8: Synthesis of Compound 366

(2.5 g, 0.008 mol) was added to Intermediate 1-5 '(5.0 g, 0.010 mol) in the same manner as in Example 1 (6) except that 2-bromo-4,6-diphenyl- (Compound 366) (4.4 g, Yield: 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.71 / d, 7.61 / d, 7.41 / d, 7.33 / m, 7.22 / d, 7.14 / m) 2H (7.85 / d, 7.25 / d, 1.72 / s) 3H (7.41 / m) 6H (8.28 / d, 7.51 / m)

LC / MS: m / z = 618 [(M + 1) ^< ^{+ &}

Example  2: Synthesis of Compound 371

(One) Manufacturing example  1: Synthesis of Compound 371

(2.5 g, 0.008 mol) was added to Intermediate 1-5 '(5.0 g, 0.010 mol) in the same manner as in Example 1- (6) 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.71 / d, 7.61 / d, 7.41 / m, 7.41 / d, 7.33 / m, 7.22 / d , 7.14 / m) 2H (8.93 d, 8.28 d, 8.12 d, 7.88 m, 7.82 m, 7.51 m, 1.72 s)

LC / MS: m / z = 613 [(M + 1) ^< ^{+ &}

Example  3: Synthesis of Compound 380

(One) Manufacturing example  1: Synthesis of intermediate 3-1

3-ylboronic acid (2.1 g, 0.010 mol) was added to Intermediate 1-5 (3.0 g, 0.008 mol), and <Intermediate 3- 1> 2.8 g (yield: 73%). (m / z &lt; / RTI &gt; = 475)

(2) Manufacturing example  2: Synthesis of Compound 380

To the intermediate 3-1 (3.0 g, 0.011 mol) was added 2-bromo-4,6-diphenyl-1,3,5-triazine (3.5 g, 0.011 mol) Synthesis was conducted in the same manner to obtain 5.8 g (yield 75%) of Compound 380.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.87 / d, 7.77 / d, 7.71 / d, 7.69 / d, 7.61 / d, 7.41 / d, 7.25 / m (7.28 / d, 7.14 / m) 2H (7.33 / m, 1.72 / s)

LC / MS: m / z = 707 [(M + 1) ^&lt; ^{+ &}

Example 4: Synthesis of Compound 377

(One) Manufacturing example  1: Synthesis of Intermediate 4-1

Intermediate 4-1 was synthesized in the same manner as in Example 1 (1) except that phenylmethanamine (4.4 g, 0.041 mol) was added to 5-bromo-2-nitroaniline (3.0 g, 0.014 mol) (Yield: 79%). (M / z = 273)

(2) Manufacturing example  2: Synthesis of intermediate 4-2

Intermediate 4-2 was synthesized in the same manner as in Example 1 (2), except that methyl 2-iodobenzoate (2.9 g, 0.011 mol) was added to Intermediate 4-1 (3.0 g, 0.011 mol) (Yield: 77%). (M / z = 407)

(3) Manufacturing example  3: Synthesis of intermediate 4-3

2.3 g (yield 72%) of Intermediate 4-3 (m / z) was obtained by the same method as in Example 1- (3) except that Intermediate 4-2 (3.3 g, 0.008 mol) = 407)

(4) Manufacturing example  4: Synthesis of intermediate 4-4

2.2 g (yield 70%) of Intermediate 4-4 was obtained by the same procedure as in Example 1 (4) except that Intermediate 4-3 (3.3 g, 0.008 mol) was added. M / z = 389)

(5) Manufacturing example  5: Synthesis of intermediate 4-5

Synthesis was conducted in the same manner as in Example 1 (5), except that triisopropyl borate (2.6 g, 0.014 mol) was added to 2-bromo-9H-carbazole (3.0 g, 0.012 mol) g (yield: 75%). (m / z = 211)

(6) Manufacturing example  6: Synthesis of intermediate 4-6

Intermediate 4-6 (2.1 g, 0.010 mol) was added to Intermediate 4-4 (3.0 g, 0.008 mol) and 2.7 g of Intermediate 4-6 was synthesized in the same manner as in Example 1- (Yield: 70%). (M / z = 475)

(7) Manufacturing example  7: Synthesis of Compound 377

To the intermediate 4-6 (5.0 g, 0.010 mol) was added 2-bromo-4,6-diphenyl-1,3,5-triazine (3.1 g, 0.010 mol) Synthesis was conducted in the same manner to obtain 4.9 g (yield 70%) of <Compound 377>.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.18 / d, 7.99 / d, 7.94 / d, 7.79 / d, 7.62 / s, 7.47 / d, 7.40 / m, 7.37 / m M, 7,30 / d, 7.26 / d, 7.25 / m) 2H (1.72 / s) 3H (7.41 / m) 6H (8.28 / d, 7.51 /

LC / MS: m / z = 707 [(M + 1) ^&lt; ^{+ &}

Example  5: Synthesis of Compound 420

(One) Manufacturing example  1: Synthesis of Compound 420

Synthesis was conducted in the same manner as in Example 1 (6), except that 4-bromodibenzo [b, d] thiophene (1.8 g, 0.007 mol) was added to Intermediate 1-5 '(4.1 g, 0.008 mol) 420> 2.9 g (yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 8.41 / d, 8.20 / d, 7.98 / d, 7.71 / d, 7.61 / d, 7.58 / m, 7.52 / m, 7.50 / m , 7.41 / d, 7.41 / m, 7.33 / m, 7.22 / d, 7.14 / m) 2H (8.28 / d, 7.51 / m, 1.72 / s)

LC / MS: m / z = 569 [(M + 1) ^&lt; ^{+ &}

Example  6: Synthesis of Compound 435

(One) Manufacturing example  1: Synthesis of intermediate 6-1

Synthesis was conducted in the same manner as in Example 1 (6), except that 1,3,5-tribromobenzene (2.2 g, 0.007 mol) was added to Intermediate 1-4 '(3.05 g, 0.008 mol) 1> 2.7 g (yield 70%). (m / z = 544)

(2) Manufacturing example  2: Synthesis of Compound 435

Synthesis was conducted in the same manner as in Example 1-Preparation Example (2), except that 9H-carbazole (4.4 g, 0.018 mol) was added to Intermediate 6-1 (5.0 g, 0.009 mol) to obtain 4.7 g (yield: 73% %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.71 / d, 7.61 / d, 7.41 / m, 7.41 / d, 7.33 / m, 7.22 / d, 7.20 / s, 7.14 / m) 2H (8.55 7.51 / m, 7.50 / m, 7.33 / m, 7.29 / m, 7.25 / m, 1.72 / s)

LC / MS: m / z = 717 [(M + 1) ^&lt; ^{+ &}

Example  7: Synthesis of Compound 393

(One) Manufacturing example  1: Synthesis of Intermediate 7-1

100 mL of 1,2-dichlorobenzene was added to triphenylphosphine (4.5 g, 0.017 mol) in 2-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) and the mixture was reacted at 180 ° C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and the resultant product was separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 4.2 g (m / z = 246)

(2) Manufacturing example  2: Synthesis of intermediate 7-2

After dissolving 30 mL of anhydrous THF in Intermediate 7-1 (3.0 g, 0.012 mol), 5.9 mL of n-BuLi (2.5 M) was slowly added dropwise at -78 ° C. After maintaining for 1 hour, triisopropyl borate (3.4 g, 0.018 mol) was added and stirred at room temperature for 24 hours. After completion of the reaction, 1 N HCl was added and the mixture was stirred for 1 hour. After separation into EA: H ₂ O, the reaction product was recrystallized with n-hexane to obtain 1.8 g (yield 70% 211)

(3) Manufacturing example  3: Synthesis of intermediate 7-3

Intermediate 7-3 (2.7 g, 0.010 mol) was added to intermediate 1-4 (3.0 g, 0.008 mol) and synthesized in the same manner as in Example 1- (6) (Yield: 70%). (m / z < / RTI > = 475)

(4) Manufacturing example  4: Synthesis of compound 393

Synthesis was conducted in the same manner as in Example 1 (2) except that 4-bromodibenzo [b, d] thiophene (2.9 g, 0.011 mol) was added to Intermediate 7-3 (3.0 g, 0.011 mol) > 5.6 g (yield 77%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.98 / d, 7.94 / d, 7.79 / d, 7.71 / d, 7.61 / d, 7.59 / d, 7.50 / m, 7.43 / m M, 7.32 / d, 7.14 / m) 2H (8.45 / d, 8.28 / d, 7.52 / m, 7.51 / m, 7.33 / m, 1.72 / s)

LC / MS: m / z = 658 [(M + 1) ^&lt; ^{+ &}

Example  8: Synthesis of Compound 395

(One) Manufacturing example  1: Synthesis of Intermediate 8-1

Intermediate 8-1 was synthesized in the same manner as in Example 1 (2) except that iodobenzene (1.8 g, 0.009 mol) was added to 3,6-dibromo-9H-carbazole (3.0 g, 0.009 mol) 2.6 g (yield 71%) was obtained. (M / z = 401)

(2) Manufacturing example  2: Synthesis of Intermediate 8-2

<Intermediate 8-2> 2.7 (2 g, 0.008 mol) was added to the intermediate 8-1 (3.0 g, 0.007 mol) and bis (pinacolato) dibron g (yield: 77%). (m / z = 495)

(3) Manufacturing example  3: Synthesis of Compound 395

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 8 (5.0 g, 0.010 mol) was added to intermediate 1-4 (6.0 g, 0.016 mol) 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d, 7.45 / m) 2H (7.77 / s, 7.71 / d, 7.61 / d, 7.58 7.41 / d, 7.33 / m, 7.22 / d, 7.14 / m) 4H (8.28 / d, 7.51 / m, 1.72 / s)

LC / MS: m / z = 861 [(M + 1) ^&lt; ^{+ &}

Example  9: Synthesis of Compound 405

(One) Manufacturing example  1: Synthesis of compound 405

Synthesis was conducted in the same manner as in Example 1 (6), except that triphenylen-2-ylboronic acid (5.4 g, 0.020 mol) was added to Intermediate 6-1 (3.0 g, 0.009 mol) (Yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.71 / d, 7.61 / d, 7.41 / d, 7.41 / m, 7.33 / m, 7.22 / d, 7.14 / m) 2H (9.15 / s, 8.28 d, 8.08 / d, 7.51 / m, 1.72 / s) 3H (7.66 /

LC / MS: m / z = 840 [(M + 1) ^&lt; ^{+ &}

Example  10: Synthesis of Compound 407

(One) Manufacturing example  1: Synthesis of compound 407

Was synthesized in the same manner as in Example 1 (6), except that Intermediate 6-1 (3.0 g, 0.009 mol) and dibenzo [b, d] thiophen-4-ylboronic acid (4.6 g, 0.020 mol) <Compound 407> 4.5 g (yield 67%) was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.71 / d, 7.61 / d, 7.41 / d, 7.41 / m, 7.33 / m, 7.22 / d, 7.14 / m) 2H (8.45 / d, 8.41 7.58 / m, 7.50 / m, 1.72 / s) 3H (7.66 / s)

LC / MS: m / z = 751 [(M + 1) ^&lt; ^{+ &}

Example  11: Synthesis of compound 441

(One) Manufacturing example  1: Synthesis of intermediate 11-1

The same procedure as in Example 1 (6) was repeated except that 9H-carbazol-3-ylboronic acid (3.0 g, 0.014 mol) and 2-bromo-9,9- Synthesis was conducted in the same manner to obtain 3.2 g (yield 67%) of Intermediate 11-1. (m / z = 359)

(2) Manufacturing example  2: Synthesis of compound 441

(3.2 g, 0.008 mol) was added to Intermediate 1-4 (3.0 g, 0.008 mol) in the same manner as in Example 1- (2) 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.93 / d, 7.69 / d, 7.63 / d, 7.61 / d, 7.55 / d, 7.41 / m, 7.41 / d 7.28 / m, 7.17 / m) 2H (8.28 / d, 7.87 / d, 7.77 / s, 7.51 / m, 7.26 / / s)

LC / MS: m / z = 668 [(M + 1) ^&lt; ^{+ &}

Example  12: Synthesis of Compound 450

(One) Manufacturing example  1: Synthesis of Intermediate 12-1

Synthesis was carried out in the same manner as in Example 1 (6) except that 1,4-dibromobenzene (3.5 g, 0.015 mol) and dibenzo [b, d] thiophen-4-ylboronic acid (4.1 g, 0.018 mol) To obtain 3.6 g (yield 71%) of Intermediate 12-1. (m / z < / RTI > = 339)

(2) Manufacturing example  2: Synthesis of intermediate 12-2

Intermediate 12-2 was obtained from Intermediate 7-2 (2.1 g, 0.010 mol) and Intermediate 12-1 (2.7 g, 0.008 mol) in the same manner as in Example 1- (6) (Yield: 67%). (m / z = 425)

(3) Manufacturing example  3: Synthesis of Compound 450

Synthesis was conducted in the same manner as in Example 1-Preparation Example (2), except that Intermediate 12 (3.4 g, 0.008 mol) was added to Intermediate 1-4 (3.0 g, 0.008 mol) 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.45 / d, 8.41 / d, 8.20 / d, 7.98 / d, 7.94 / d, 7.79 / d, 7.61 / d, 7.59 / d 7.58 m, 7.50 m, 7.50 m, 7.43 m, 7.41 / d, 7.41 m, 7.33 m, 7.27 m, 7.25 m, 7.14 m) , 7.26 / d, 1.72 / s) 4H (7.25 / d)

LC / MS: m / z = 734 [(M + 1) ^&lt; ^{+ &}

Example  13: Synthesis of compound 471

(One) Manufacturing example  1: Synthesis of compound 471

(2.5 g, 0.011 mol) was added to Intermediate 3-1 (3.0 g, 0.011 mol) and the compound obtained in Synthesis Example 2 (5.8 g, yield 75% %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.93 / d, 8.55 / d, 8.12 / d, 7.94 / d, 7.90 / m, 7.88 / m, 7.87 / d, 7.82 / m, 7.77 / s , 7.71 / d, 7.69 / d, 7.61 / d, 7.41 / d, 7.41 / m, 7.25 / m, 7.22 / d, 7.14 / , 7.51 / m, 7.33 / m, 7.20 / s)

LC / MS: m / z = 702 [(M + 1) ^&lt; ^{+ &}

Example  14: Synthesis of compound 476

(One) Manufacturing example  1: Synthesis of intermediate 14-1

Phenylboronic acid (1.8 g, 0.015 mol) was added to 2-bromo-5-chloro-1H-benzo [d] imidazole (3.0 g, 0.013 mol) in the same manner as in Example 1- To obtain 2.1 g (yield: 71%) of Intermediate 14-1 (m / z = 228)

(2) Manufacturing example  2: Synthesis of intermediate 14-2

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 14-1 (1.8 g, 0.008 mol) and Intermediate 14-2> 2.9 (4.4 g, 0.010 mol) g (yield: 71%). (m / z = 502)

(3) Manufacturing example  3: Synthesis of intermediate 14-3

Intermediate 14-3> 4.8 g (0.010 mol) was obtained by synthesizing 1,4-dibromobenzene (2.4 g, 0.010 mol) in Intermediate 14-2 (5.0 g, 0.010 mol) g (yield: 73%). (m / z = 657)

(4) Manufacturing example  4: Synthesis of intermediate 14-4

Synthesis was conducted in the same manner as in Example 1 (5), except that bis (pinacolato) dibron (2.5 g, 0.010 mol) was added to Intermediate 14-3 (5.0 g, 0.008 mol) g (yield: 73%). (m / z = 704)

(5) Manufacturing example  5: Synthesis of compound 476

Synthesis was conducted in the same manner as in Example 1-Preparation Example (6), except that 2-bromotriphenylene (2.1 g, 0.007 mol) was added to Intermediate 14-4 (5.6 g, 0.008 mol) %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.29 / d, 8.18 / d, 8.07 / d, 8.04 / d, 7.92 / d, 7.71 / d, 7.61 / d, 7.41 / d 8.38 / d, 7.88 / d, 7.79 / d, 7.68 / d, 7.41 / m, 1.72 / s) / d, 7.51 / m)

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

Example  15: Synthesis of Compound 531

(One) Manufacturing example  1: Synthesis of intermediate 15-1

(Intermediate 15-1) was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.7 g, 0.014 mol) was added to 3-iodo-1H-indole (3.0 g, 0.012 mol) 1.6 g (yield 68%) of (m / z = 193)

(2) Manufacturing example  2: Synthesis of intermediate 15-2

Intermediate 15-2 was synthesized in the same manner as in Example 1 (2) except that methyl 2,6-dibromobenzoate (2.9 g, 0.010 mol) was added to Intermediate 15-1 (1.4 g, 0.007 mol) 1.8 g (yield 62%) of (m / z = 406)

(3) Manufacturing example  3: Synthesis of intermediate 15-3

2.3 g (yield: 70%) of Intermediate 15-3 (3.2 g, 0.008 mol) was obtained in the same manner as in Example 1- (3) = 406)

(4) Manufacturing example  4: Synthesis of intermediate 15-4

3.1 g (yield: 73%) of Intermediate 15-4 was obtained by the same procedure as in Example 1 (4), except that Intermediate 15-3 (4.5 g, 0.011 mol) = 388)

(5) Manufacturing example  5: Synthesis of intermediate 15-4 '

Intermediate 15-4 'was synthesized in the same manner as in Example 1 (5) except that bis (pinacolato) dibron (2.5 g, 0.010 mol) was added to Intermediate 15-4 (3.0 g, 0.008 mol) 2.5 g (yield 71%) of the title compound was obtained (m / z = 435)

(6) Manufacturing example  6: Synthesis of intermediate 15-5

Intermediate 15-5 was synthesized in the same manner as in Example 1 (6) except that 1,4-dibromobenzene (1.8 g, 0.008 mol) was added to Intermediate 15-4 '(4.0 g, 0.009 mol) 2.6 g (yield: 71%) was obtained. (M / z = 464)

(7) Manufacturing example  7: Synthesis of intermediate 15-5 '

Intermediate 15-5 'was synthesized in the same manner as in Example 1 (5) except that bis (pinacolato) dibron (2.5 g, 0.010 mol) was added to Intermediate 15-5 (3.7 g, 0.008 mol) 2.9 g (71% yield) of the title compound was obtained. (M / z = 511)

(8) Manufacturing example  8: Synthesis of Compound 531

Synthesis was conducted in the same manner as in Example 1 (4) except that 3-bromo-9-phenyl-9H-carbazole (2.6 g, 0.008 mol) was added to Intermediate 15-5 '(5.0 g, 0.010 mol) <Compound 531> 3.6 g (yield: 71%) was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.99 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.71 / d, 7.69 / d, 7.45 / m, 7.41 / m 7.51 / m, 7.50 / d, 7.33 / m, 1.72 / s) 4H (7.25 / m, 7.36 / s, 7.34 / m, 7.25 / / d)

LC / MS: m / z = 627 [(M + 1) ^&lt; ^{+ &}

Example  16: Synthesis of compound 540

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

Intermediate 16-1 (1.4 g, 0.007 mol) was synthesized in the same manner as in Example 1 (2), except that methyl 2-bromobenzoate (2.1 g, 0.010 mol) (Yield: 62%). (M / z = 327)

(2) Manufacturing example  2: Synthesis of intermediate 16-2

1.8 g (yield 70%) of <Intermediate 16-2> was obtained by the same method as employed in the preparation example (3) of Example 1, except that Intermediate 16-1 (2.6 g, 0.008 mol) = 327)

(3) Manufacturing example  3: Synthesis of intermediate 16-3

2.5 g (yield 73%) of <Intermediate 16-3> was obtained by the same method as in Example 1 (4), except that Intermediate 16-2 (3.6 g, 0.011 mol) = 309)

(4) Manufacturing example  4: Synthesis of intermediate 16-4

100 mL of DMF was added to N-bromosuccinimide (1.8 g, 0.010 mol) in Intermediate 16-3 (3.0 g, 0.010 mol) and the mixture was reacted at 20 ° C for 8 hours with stirring. After completion of the reaction H ₂ 0: After phase separation with ethyl acetate and column purification (n-Hexane: MC) to give the intermediate 16-4 1.9 g (48%) ( m / z = 388).

(5) Manufacturing example  5: Synthesis of intermediate 16-5

Intermediate 16-5 was synthesized by the same method as in Example 1 (5) except that bis (pinacolato) dibron (2.5 g, 0.010 mol) was added to Intermediate 16-4 (3.0 g, 0.008 mol) 2.5 g (73%) of (m / z = 435)

(6) Manufacturing example  6: Synthesis of intermediate 16-6

Intermediate 16-6 was synthesized in the same manner as in Example 1- (6), except that 1,4-dibromobenzene (1.4 g, 0.006 mol) was added to Intermediate 16-5 (3.0 g, 0.007 mol) 2.0 g (73%) of (m / z = 464)

(7) Manufacturing example  7: Synthesis of intermediate 16-7

(2.5 g, 0.020 mol) and N-bromosuccinimide (3.5 g, 0.020 mol) were added to the reaction mixture and the mixture was reacted in the same manner as in Example 16 (4) (M / z = 335) of <Intermediate 16-7> (yield: 43%).

(8) Manufacturing example  8: Synthesis of intermediate 16-8

To the intermediate 25-1 (5.0 g, 0.020 mol) was added 100 mL of THF to phenyl-boronic acid (2.4 g, 0.024 mol) and the mixture was reacted at -78 ° C for 5 hours with stirring. After completion of the reaction H ₂ 0: column purification after separating layer on MC: the (n-HEXANE MC) to afford the intermediate 16-8 4.9 g (72%) ( m / z = 339)

(9) Manufacturing example  9: Synthesis of intermediate 16-9

100 mL of THF was added to intermediate 16-8 (6.3 g, 0.020 mol) and methyl magnesium iodide (4.0 g, 0.024 mol), and the mixture was reacted at -78 ° C for 5 hours with stirring. After completion of the reaction H ₂ 0: column purification after separating layer on MC: the (n-HEXANE MC) to afford the intermediate 16-9 5.3 g (90%) ( m / z = 296)

(10) Manufacturing example  10: Synthesis of intermediate 16-10

(2.5 g, 0.010 mol) was added to intermediate 16-9 (3.0 g, 0.010 mol), and 2.8 g of Intermediate 16-10 (yield: 75%) was obtained in the same manner as in Example 1- %). (M / z = 372)

(11) Manufacturing example  11: Synthesis of compound 540

Compound 16 was synthesized in the same manner as in Example 1 (2) except that Intermediate 16-10 (4.1 g, 0.011 mol) was added to Intermediate 16-6 (5.0 g, 0.011 mol) 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.19 / d, 8.12 / d, 7.93 / d, 7.76 / d, 7.63 / d, 7.50 / m, 7.45 / m, 7.41 / m, 7.40 / m 7.7 / d, 7.68 / d, 7.29 / d, 7.36 / d, 7.26 / d, 7.25 / , 7.51 / m, 7.50 / d) 4H (1.72 / s)

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

Example  17: Synthesis of compound 572

(One) Manufacturing example  1: Synthesis of intermediate 17-1

Intermediate 17 (3.0 g, 0.008 mol) was added to 3,6-dibromo-9H-carbazole (2.6 g, 0.008 mol) -1> 3.6 g (yield: 71%). (M / z = 632)

(2) Manufacturing example  2: Synthesis of compound 572

Synthesis was conducted in the same manner as in Example 1 (2) except that 2-phenyl-1H-benzo [d] imidazole (3.1 g, 0.016 mol) was added to Intermediate 17-1 (5.0 g, 0.008 mol) To obtain 5.6 g (yield: 81%) of the compound 572. (m / z = 632)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.94 / d, 7.63 / d, 7.62 / d, 7.36 / s, 7.34 / m, 7.31 / d, 7.27 / m, 7.04 / d M) 2H (8.56 / d, 7.59 / d, 7.52 / d, 7.50 / s, 7.26 / d, 1.72 / s)

LC / MS: m / z = 860 [(M + 1) ^&lt; ^{+ &}

Example  18: Synthesis of compound 573

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

Intermediate 15-5 (3.7 g, 0.008 mol) was reacted with 1,3,5-tribromobenzene (2.2 g, 0.007 mol), and the reaction mixture was treated in the same manner as in Example 1- (M / z = 619) of 3.1 g (yield 71%).

(2) Manufacturing example  2: Synthesis of compound 573

Synthesis was carried out in the same manner as in Example 1 (2) except that 2-phenyl-1H-benzo [d] imidazole (3.1 g, 0.016 mol) was added to Intermediate 18-1 (5.0 g, 0.008 mol) Compound 573> 4.8 g (71% yield) was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.71 / d, 7.36 / s, 7.34 / m, 7.33 / m, 7.22 / d, 7.20 / s, 7.04 / d) 2H (7.52 m), 6H (7.51 / m), &lt; / RTI &gt;

LC / MS: m / z = 847 [(M + 1) ^&lt; ^{+ &}

Example  19: Synthesis of compound 596

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

2.8 g (71%) of Intermediate 19-1 was synthesized in the same manner as in Example 1 (6) except that phenyl boronic acid (3.6 g, 0.030 mol) was added to perchloropyrimidine (3.0 g, 0.013 mol) ). (M / z = 301)

(2) Manufacturing example  2: Synthesis of intermediate 19-2

Intermediate 19-2> 3.6 (4-aminopyridine) was synthesized in the same manner as in Example 1 (5) except that bis (pinacolato) dibron (3.0 g, 0.012 mol) g (yield: 74%). (m / z = 484)

(3) Manufacturing example  3: Synthesis of intermediate 19-3

To the intermediate 19-2 (5.0 g, 0.010 mol) was added 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 0.008 mol) Synthesis was conducted in the same manner to obtain 3.5 g (yield: 74%) of Intermediate 19-3 (m / z = 589)

(4) Manufacturing example  4: Synthesis of compound 596

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 15-3 (3.0 g, 0.009 mol) and Intermediate 19-3 (6.5 g, 0.011 mol) 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.71 / d, 7.36 / s, 7.34 / m, 7.33 / m, 7.22 / d, 7.04 / d) 2H (7.52 / d, 1.72 / s) 4H (8.28 / d, 7.79 / d) 5H (7.41 / m) 10H (7.51 /

LC / MS: m / z = 771 [(M + 1) ^&lt; ^{+ &}

Example  20: Synthesis of Compound 609

(One) Manufacturing example  1: Synthesis of intermediate 20-1

Intermediate 20-4 was synthesized in the same manner as in Example 1- (6) except that 1,3,5-tribromobenzene (2.5 g, 0.008 mol) was added to Intermediate 15-4 '(4.0 g, 0.009 mol) 1> 3.1 g (yield: 71%). (M / z = 543)

(2) Manufacturing example  2: Synthesis of intermediate 20-2

Intermediate 20-2 was synthesized according to the same procedure as in Preparation Example 5 (5), except that bis (pinacolato) dibron (2.7 g, 0.011 mol) was added to Intermediate 20-1 (4.9 g, 0.009 mol) g (yield: 71%). (m / z = 637)

(3) Manufacturing example  3: Synthesis of Compound 609

Synthesis was carried out in the same manner as in Example 1 (4), except that 2-bromo-1,8-naphthyridine (3.0 g, 0.014 mol) was added to Intermediate 20-2 (5.0 g, 0.008 mol) > 3.2 g (yield 71%).

7.36 / s, 7.32 / d, 7.02 / d, 7.04 / d (1 H-NMR (200 MHz, CDCl ₃ ) D, 7.61 / d, 7.52 / d, 7.51 / m, 7.41 / m, 1.72 / s)

LC / MS: m / z = 642 [(M + 1) ^&lt; ^{+ &}

Example  21: Synthesis of Compound 647

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

Was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.7 g, 0.014 mol) was added to 2-iodo-1H- benzo [d] imidazole (3.0 g, 0.012 mol) 21-1> 1.5 g (yield 65%). (M / z = 194)

(2) Manufacturing example  2: Synthesis of intermediate 21-2

Intermediate 21-1 (2.0 g, 0.010 mol) and methyl 3-bromo-6-fluoropicolinate (2.3 g, 0.010 mol) were placed in a manner similar to that used in Example 1- 2> 2.2 g (yield 64%). (M / z = 347)

(3) Manufacturing example  3: Synthesis of intermediate 21-3

Intermediate 21-2 (3.0 g, 0.009 mol) was used to synthesize 1.7 g (yield 72%) of Intermediate 21-3 in the same manner as in Example 1- (3) = 347)

(4) Manufacturing example  4: Synthesis of Intermediate 21-4

2.1 g (yield: 70%) of Intermediate 21-4 was obtained by the same procedure as in Example 1 (4), except that Intermediate 21-3 (3.0 g, 0.009 mol) = 329)

(5) Manufacturing example  5: Synthesis of intermediate 21-5

(Pinacolato) dibron (2.5 g, 0.010 mol) was added to 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.0 g, 0.008 mol) 5) (2.6 g, yield 74%) as an intermediate 21-5 (m / z = 435).

(6) Manufacturing example  6: Synthesis of Compound 647

Intermediate 21-5 (3.9 g, 0.011 mol) was added to Intermediate 21-4 (3.0 g, 0.009 mol) and the compound was synthesized by the same method as in Example 1 (4) 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.82 / d, 7.77 / d, 7.61 / d, 7.41 / d, 7.14 / m) 2H (8.81 / d, 7.88 / d, 1.72 / s) 3H (7.41 / m) 6H (8.28 / d, 7.51 / m)

LC / MS: m / z = 619 [(M + 1) ^&lt; ^{+ &}

Example  22: Synthesis of Compound 656

(One) Manufacturing example  1: Synthesis of Intermediate 22-1

Intermediate 22-1 (2.0 g, 0.010 mol) was synthesized in the same manner as in Example 1 (2) except that methyl 2-bromo-5-iodoisonicotinate (5.1 g, 0.015 mol) 1> 2.8 g (yield: 68%). (M / z = 408)

(2) Manufacturing example  2: Synthesis of Intermediate 22-2

Intermediate 22-1 (3.0 g, 0.007 mol) was synthesized in the same manner as in Example 1 (3) to give 1.9 g (yield 67%) of Intermediate 22-2. M / z = 408)

(3) Manufacturing example  3: Synthesis of intermediate 22-3

2.1 g (yield 74%) of Intermediate 22-3 was obtained by the same method as in Example 1 (4), except that Intermediate 22-2 (3.0 g, 0.007 mol) was added. M / z = 408)

(4) Manufacturing example  4: Synthesis of intermediate 22-4

dibromobenzene (2.1 g, 0.009 mol) was added to triphenylen-2-ylboronic acid (3.0 g, 0.011 mol) in the same manner as in Example 1 (6) > 2.6 g (yield: 74%). (M / z = 383)

(5) Manufacturing example  5: Synthesis of intermediate 22-5

(Intermediate 22-5) 2.5 (2.5 g, 0.010 mol) was added to Intermediate 22-4 (3.0 g, 0.008 mol) and bis (pinacolato) dibron g (yield: 74%). (m / z = 430)

(6) Manufacturing example  6: Synthesis of compound 656

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 22-5 (4.3 g, 0.010 mol) and Intermediate 22-4 (3.0 g, 0.008 mol) 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.60 / s, 8.18 / d, 8.04 / d, 7.91 / d, 7.61 / d, 7.41 / d, 7.41 / m, 7.14 / m 7.81 / d, 7.88 / d, 7.82 / m, 7.51 / m, 1.72 / s)

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

Example  23: Synthesis of Compound 662

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

2-carboxylate (5.1 g, 0.015 mol) was added to Intermediate 21-1 (2.0 g, 0.010 mol) in the same manner as in Example 1 (2) (M / z = 409) of <Intermediate 23-1> (yield: 68%).

(2) Manufacturing example  2: Synthesis of intermediate 23-2

2.7 g (yield 72%) of Intermediate 23-2 was obtained by the same method as in Example 1 (3), except that Intermediate 23-1 (3.0 g, 0.009 mol) was added. M / z = 409)

(3) Manufacturing example  3: Synthesis of intermediate 23-3

2.0 g (yield 74%) of Intermediate 23-3 was obtained in the same manner as in Example 1- (4), except that Intermediate 23-2 (3.0 g, 0.007 mol) = 391)

(4) Manufacturing example  4: Synthesis of intermediate 23-4

Synthesis was carried out in the same manner as in Example 1 (6), except that 1,4-dibromobenzene (1.9 g, 0.008 mol) was added to 9-phenyl-9H-carbazol-3-ylboronic acid (3.0 g, 0.010 mol) 2.3 g (yield: 72%) of Intermediate 23-4 was obtained (m / z = 398)

(5) Manufacturing example  5: Synthesis of intermediate 23-5

(Intermediate 23-5) 2.6 (0.2 g, 0.010 mol) was added to Intermediate 23-4 (3.0 g, 0.008 mol) and bis (pinacolato) dibron g (yield: 72%). (m / z = 445)

(6) Manufacturing example  6: Synthesis of Compound 662

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 23-5 (3.0 g, 0.008 mol) and Intermediate 23-5 (4.5 g, 0.010 mol) 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.54 / s, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.61 / d, 7.45 / m, 7.41 / m 7.51 / m, 7.14 / m) 2H (8.30 d, 8.28 d, 7.85 d, 7.58 m, 7.51 m, 7.50 d, 1.72 s)

LC / MS: m / z = 630 [(M + 1) ^&lt; ^{+ &}

Example  24: Synthesis of Compound 651

(One) Manufacturing example  1: Synthesis of intermediate 24-1

Synthesis was conducted in the same manner as in Example 1 (6), except that phenyl boronic acid (1.7 g, 0.014 mol) was added to 8-iodo-7H-purine (3.0 g, 0.012 mol) 1.4 g (yield: 60%) was obtained. (M / z = 196)

(2) Manufacturing example  2: Synthesis of intermediate 24-2

Intermediate 24-2 was synthesized in the same manner as in Example 1 (2) except that methyl 2,6-dibromobenzoate (4.4 g, 0.015 mol) was added to Intermediate 24-1 (2.0 g, 0.010 mol) 2.8 g (yield 68%) of the title compound was obtained. (M / z = 409)

(3) Manufacturing example  3: Synthesis of intermediate 24-3

2.1 g (yield 72%) of Intermediate 24-3 was obtained in the same manner as in Example 1- (3), except that Intermediate 24-2 (3.0 g, 0.007 mol) = 409)

(4) Manufacturing example  4: Synthesis of intermediate 24-4

2.0 g (yield 72%) of <Intermediate 24-4> was obtained by the same method as in Example 1- (4), except that Intermediate 24-3 (3.0 g, 0.007 mol) = 391)

(5) Manufacturing example  5: Synthesis of Compound 651

Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 21-5 (4.4 g, 0.010 mol) was added to Intermediate 24-4 (3.0 g, 0.008 mol) 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.86 / s, 7.86 / s, 7.61 / d, 7.60 / d) 2H (7.85 / d, 7.25 / d, 1.72 / s) 3H (7.41 / m ) 6H (8.28 / d, 7.51 / m)

LC / MS: m / z = 620 [(M + 1) ^&lt; ^{+ &}

Example  25: Synthesis of compound 664

(One) Manufacturing example  1: Synthesis of intermediate 25-1

1,2,3-tribromobenzene 5 (4.4 g, 0.014 mol) was added to 2-amino-5-chlorophenol (3.0 g, 0.014 mol) and 100 mL of PPA (polyphosphoric acid) was added thereto and reacted at 180 ° C. for 4 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and the product was separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 2.1 g (51%) of Intermediate 25-1 (m / z = 296)

(2) Manufacturing example  2: Synthesis of intermediate 25-2

Intermediate 25-1 (3.0 g, 0.010 mol) was reacted with carbonimidic dibromide (2.2 g, 0.012 mol), and the reaction mixture was reacted in the same manner as in Example 1 (2) 25-2> 1.8 g (yield: 57%). (M / z = 321)

(3) Manufacturing example  3: Synthesis of intermediate 25-3

Intermediate 25-3 was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.5 g, 0.012 mol) was added to Intermediate 25-2 (3.0 g, 0.010 mol) Yield: 70%). (M / z = 318)

(4) Manufacturing example  4: Synthesis of Compound 664

Synthesis was conducted in the same manner as in Example 1 (4) to give Intermediate 22-5 (5.1 g, 0.012 mol) and Intermediate 25-3 (3.0 g, 0.010 mol) 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.64 / d, 7.41 / m, 7.31 / d, 7.18 / m, 7.08 / d) 2H (8.93 d, 8.28 d, 8.12 d, 7.88 m, 7.82 m, 7.51 m, 7.51 d) 4H (7.25 d)

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

Example  26: Synthesis of Compound 671

(One) Manufacturing example  1: Synthesis of intermediate 26-1

1,2,3-tribromobenzene (3.7 g, 0.012 mol) was added to 5-chlorobenzene-1,2-diamine (2.2 g, 0.010 mol) in the same manner as in Example 25- 1.4 g (yield: 48%) of Intermediate 26-1 (m / z = 295) was obtained.

(2) Manufacturing example  2: Synthesis of intermediate 26-2

<Intermediate 26-2> 1.8 (dibromoethene) was synthesized in the same manner as in Example 1 (2) except that 1,1-dibromoethene (2.1 g, 0.012 mol) was added to Intermediate 26-1 g (yield: 57%). (m / z = 320)

(3) Manufacturing example  3: Synthesis of intermediate 26-3

2.0 g of Intermediate 26-3 was synthesized in the same manner as in Example 1 (6) except that phenyl boronic acid (1.5 g, 0.012 mol) was added to Intermediate 26-2 (3.0 g, 0.010 mol) Yield: 71%). (M / z = 283)

(4) Manufacturing example  4: Synthesis of intermediate 26-4

(2.5 g, 0.010 mol) was added to intermediate 26-3 (3.0 g, 0.010 mol), and 2.8 g (yield: 71%) of Intermediate 26-4 was synthesized in the same manner as in Example 1- %). (M / z = 393)

(5) Manufacturing example  5: Synthesis of Compound 671

Intermediate 21-5 (4.3 g, 0.010 mol) was added to Intermediate 26-4 (3.0 g, 0.008 mol) and the compound obtained in Synthesis Example 6 was reacted with 3.9 g (yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.43 / d, 7.15 / d, 6.97 / m, 6.95 / d, 6.89 / s, 6.81 / m, 6.46 / d) 2H (7.85 / d, 7.25 / d, 7.20 / m, 6.63 / d) 3H (7.41 / m) 6H (8.28 / d, 7.51 / d)

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

Example  27: Synthesis of compound 678

(One) Manufacturing example  1: Synthesis of intermediate 27-1

1,2,3-tribromobenzene-6 (3.7 g, 0.012 mol) was added to benzene-1,2-diamine (1.9 g, 0.010 mol) (M / z = 261) was obtained in an amount of 1.4 g (yield: 52%).

(2) Manufacturing example  2: Synthesis of intermediate 27-2

<Intermediate 26-2> 1.7 (1) Synthesis was conducted in the same manner as in Example 1 (2) except that 1,1-dibromoethene (2.1 g, 0.012 mol) was added to Intermediate 27-1 g (yield: 59%). (m / z = 286)

(3) Manufacturing example  3: Synthesis of intermediate 27-3

2.1 g (intermediate 27-3) was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.5 g, 0.012 mol) was added to Intermediate 27-2 (3.0 g, 0.0010 mol) Yield: 73%). (M / z = 283)

(4) Manufacturing example  4: Synthesis of Compound 678

Synthesis was conducted in the same manner as in Example 1 (2) to give Intermediate 23-4 (4.0 g, 0.010 mol) and Intermediate 27-3 (3.0 g, 0.0010 mol) 77%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.45 / m, 7.41 / m, 7.37 / d, 7.33 / m 7.58 / m, 6.95 / d, 6.94 / m, 6.63 / d, 6.46 / d) 2H (8.28 / d, 7.58 / , 6.69 / d)

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

Example  28: Synthesis of compound 668

(One) Manufacturing example  1: Synthesis of intermediate 28-1

1,2,3-tribromobenzene6 (3.7 g, 0.012 mol) was added to 2-amino-5-chlorobenzenethiol (2.4 g, 0.010 mol) (M / z = 312) (yield: 41%).

(2) Manufacturing example  2: Synthesis of intermediate 28-2

Intermediate 28-2 1.9 g (0.012 mol) was obtained by synthesizing 1,1-dibromoethene (2.1 g, 0.012 mol) in Intermediate 28-1 (3.1 g, 0.010 mol) g (yield: 55%). (m / z = 337)

(3) Manufacturing example  3: Synthesis of intermediate 28-3

2.1 g (intermediate 28-3) was synthesized in the same manner as in Example 1 (6) except that phenyl boronic acid (1.5 g, 0.011 mol) was added to Intermediate 28-2 (3.0 g, 0.0009 mol) Yield: 71%). (M / z = 334)

(4) Manufacturing example  4: Synthesis of compound 668

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 22-5 (4.7 g, 0.011 mol) and Intermediate 28-3 (3.0 g, 0.0009 mol) 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.53 / d, 7.48 / d, 7.41 / m, 7.40 / s, 7.33 / d, 7.20 / d , 7.02 / m) 2H (8.93 d, 8.28 d, 8.12 d, 7.88 m, 7.82 m, 7.51 m)

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

Example  29: Synthesis of Compound 680

(One) Manufacturing example  1: Synthesis of intermediate 29-1

1,2-dibromobenzene6 (3.7 g, 0.012 mol) was added to 6-bromo-3-chloro-2- (trimethylsilyl) aniline (2.8 g, 0.010 mol) To obtain 1.5 g (yield: 45%) of Intermediate 29-1 (m / z = 338)

(2) Manufacturing example  2: Synthesis of intermediate 29-2

Intermediate 29-2> 1.8 (2.0 g, 0.011 mol) was synthesized in the same manner as in Example 1 (2) except that 1,1-dibromoethene (2.0 g, 0.011 mol) g (yield: 55%). (m / z = 362)

(3) Manufacturing example  3: Synthesis of intermediate 29-3

Intermediate 27-3 was synthesized in the same manner as in Example 1- (6), except that phenyl boronic acid (1.2 g, 0.010 mol) was added to Intermediate 29-2 (3.0 g, 0.0008 mol) Yield: 63%). (M / z = 361)

(4) Manufacturing example  4: Synthesis of Compound 680

Synthesis was conducted in the same manner as in Example 1- (6), except that Intermediate 21-5 (4.3 g, 0.010 mol) was added to Intermediate 29-3 (3.0 g, 0.008 mol) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.17 / d, 7.75 / d, 7.72 / d, 7.68 / m, 7.46 / d, 7.37 / m) 2H (7.85 / d, 7.25 / d, 0.66 / s) 3H (7.41 / m) 6H (8.28 / d, 7.51 / m)

LC / MS: m / z = 634 [(M + 1) ^&lt; ^{+ &}

Example  30: Synthesis of compound 684

(One) Manufacturing example  1: Synthesis of intermediate 30-1

Synthesis was conducted in the same manner as in Example 1 (2) except that methyl 2-bromo-5-iodopyrimidine-4-carboxylate (5.1 g, 0.015 mol) was added to Intermediate 1-1 (2.0 g, 0.010 mol) 2.5 g (yield: 61%) of Intermediate 30-1 (m / z = 409)

(2) Manufacturing example  2: Synthesis of intermediate 30-2

Intermediate 30-1 (1.7 g, yield 60%) was obtained by the same method as in Example 1- (3), except that 3.0 g (0.007 mol) of m / z = 409)

(3) Manufacturing example  3: Synthesis of intermediate 30-3

2.2 g (yield 70%) of <Intermediate 30-3> was obtained by the same method as in Example 1- (3), except that Intermediate 30-2 (3.0 g, 0.008 mol) = 391)

(4) Manufacturing example  4: Synthesis of Compound 684

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 23-5 (3.6 g, 0.010 mol) was added to Intermediate 30-3 (3.0 g, 0.008 mol) 63%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.60 / s, 8.55 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.75 / d, 7.69 / d, 7.45 / m, 7.41 / m 7.51 / m, 7.17 / m, 7.00 / s, 6.60 / s) 2H (7.85 / d, 7.79 / d, 7.58 / )

LC / MS: m / z = 628 [(M + 1) ^&lt; ^{+ &}

Example  31: Synthesis of Compound 686

(One) Manufacturing example  1: Synthesis of intermediate 31-1

Was synthesized in the same manner as in Example 25 (1) except that 1,2,3-tribromo-4-chlorobenzene (5.6 g, 0.016 mol) was added to 2-amino-phenol (3.0 g, 0.016 mol) 2.1 g (yield: 45%) of Intermediate 31-1 (m / z = 296) was obtained.

(2) Manufacturing example  2: Synthesis of intermediate 31-2

<Intermediate 31-2> 1.6 (1 g, 0.010 mol) was synthesized in the same manner as in Example 1 (2) except that 1,1-dibromoethene (1.8 g, 0.010 mol) was added to Intermediate 31-1 g (yield: 51%). (m / z = 321)

(3) Manufacturing example  3: Synthesis of intermediate 31-3

Intermediate 31-3 was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.3 g, 0.011 mol) was added to Intermediate 31-2 (3.0 g, 0.0009 mol) Yield: 71%). (M / z = 317)

(4) Manufacturing example  4: Synthesis of Compound 686

Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 22-5 (4.7 g, 0.011 mol) was added to Intermediate 31-3 (3.0 g, 0.0009 mol) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.21 / d, 8.18 / d, 8.06 / d, 8.04 / d, 7.58 / d, 7.30 / m, 7.14 / d, 6.60 / s ), 2H (8.93 / d, 8.12 / d, 7.88 / m, 7.82 / m, 7.79 / d, 7.51 / m, 7.41 /

LC / MS: m / z = 586 [(M + 1) ^&lt; ^{+ &}

Example  32: Synthesis of Compound 689

(One) Manufacturing example  1: Synthesis of intermediate 32-1

Was synthesized in the same manner as in Example 25 (1) except that 1,2,3-tribromo-4-chlorobenzene (5.5 g, 0.015 mol) was added to 6-phosphinoaniline (3.0 g, 0.015 mol) 32-1> 1.5 g (yield 41%). (M / z = 312)

(2) Manufacturing example  2: Synthesis of intermediate 32-2

<Intermediate 32-2> 1.6 (0.010 mol) was synthesized in the same manner as in Example 1 (2) except that 1,1-dibromoethene (1.8 g, 0.010 mol) was added to Intermediate 32-1 g (yield: 47%). (m / z = 337)

(3) Manufacturing example  3: Synthesis of intermediate 32-3

Intermediate 32-3 was obtained in a yield of 2.9 g (yield: 77%). Intermediate 32-2 (3.0 g, 0.009 mol) was added bromobenzene (1.4 g, 0.009 mol) %). (M / z = 413)

(4) Manufacturing example  4: Synthesis of intermediate 32-4

Intermediate 32-4 was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.0 g, 0.008 mol) was added to Intermediate 32-3 (3.0 g, 0.007 mol) Yield: 71%). (M / z = 410)

(5) Manufacturing example  5: Synthesis of compound 689

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 21-5 (2.8 g, 0.008 mol) was added to Intermediate 32-4 (3.0 g, 0.007 mol) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.82 / d, 8.43 / d, 7.91 / m, 7.41 / m, 6.60 / s) 2H (7.85 / d, 7.79 / d, 7.51 / m, 7.41 / m, 7.25 / d) 4H (8.28 / d, 7.78 / d, 7.51 / m, 7.36 / m)

LC / MS: m / z = 683 [(M + 1) ^&lt; ^{+ &}

Example  33: Synthesis of Compound 690

(One) Manufacturing example  1: Synthesis of intermediate 33-1

1,2-dibromobenzene (3.4 g, 0.011 mol) was added to 2-bromo-3-chloro-6- (trimethylsilyl) aniline (3.0 g, 0.011 mol) To obtain 1.2 g (yield: 31%) of intermediate < 33-1 > (m / z = 338)

(2) Manufacturing example  2: Synthesis of intermediate 33-2

Intermediate 33-2> 1.6 (0.009 mol) was synthesized in the same manner as in Example 1 (2) except that 1,1-dibromoethene (1.6 g, 0.009 mol) was added to Intermediate 33-1 g (yield: 50%). (m / z = 362)

(3) Manufacturing example  3: Synthesis of intermediate 33-3

Intermediate 33-3 was synthesized in the same manner as in Example 1- (6), except that phenyl boronic acid (1.2 g, 0.010 mol) was added to Intermediate 33-2 (3.0 g, 0.008 mol) Yield: 70%). (M / z = 359)

(4) Manufacturing example  4: Synthesis of Compound 690

Synthesis was carried out in the same manner as in Example 1 (6), except that Intermediate 22-5 (3.5 g, 0.010 mol) was added to Intermediate 33-3 (3.0 g, 0.008 mol) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.27 / d, 8.18 / d, 8.04 / d, 7.72 / d, 7.68 / m, 7.52 / m, 7.50 / d, 7.46 / d (7.35 / d), 7.37 / m) 2H (8.93 d, 8.12 d, 7.88 m, 7.82 m, 7.79 d, 7.51 m, 0.66 s)

LC / MS: m / z = 628 [(M + 1) ^&lt; ^{+ &}

Example  34: Synthesis of Compound 691

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

Was synthesized in the same manner as in Example 7-Preparation Example (2), except that triisopropyl borate (3.4 g, 0.018 mol) was added to 2-iodo-1H-benzo [d] imidazole (3.0 g, 0.012 mol) -1> 1.4 g (yield: 71%). (M / z = 161)

(2) Manufacturing example  2: Synthesis of intermediate 34-2

Intermediate 34-2> 2.0 (2.0 g, 0.012 mol) was synthesized in the same manner as in Example 1- (6) except that 2,5-dibromothiophene (2.4 g, 0.010 mol) g (yield: 73%). (m / z = 279)

(3) Manufacturing example  3: Synthesis of intermediate 34-3

Intermediate 34-3 was synthesized in the same manner as in Example 1 (6) except that triphenylen-2-ylboronic acid (3.4 g, 0.012 mol) was added to intermediate 34-2 (3.0 g, 0.010 mol) 3.2 g (yield 75%) was obtained. (M / z = 426)

(4) Manufacturing example  4: Synthesis of intermediate 34-4

Intermediate 34-4 was synthesized in the same manner as in Example 1 (2), except that methyl 2-bromobenzoate (1.5 g, 0.007 mol) was added to Intermediate 34-3 (3.0 g, 0.007 mol) (Yield: 68%). (M / z = 560)

(5) Manufacturing example  5: Synthesis of intermediate 34-5

And 3.6 g (yield 72%) of Intermediate 34-5 (3.0 g, 0.009 mol) were synthesized in the same manner as in Example 1- (3) = 560)

(6) Manufacturing example  6: Synthesis of Compound 691

3.5 g (yield 72%) of Compound 691 was obtained by the same method as in Example 1- (4), except that Intermediate 34-5 (3.0 g, 0.009 mol) was added.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.61 / d, 7.41 / m, 7.40 / m, 7.37 / m, 7.30 / d, 7.26 / d , 7.14 / m) 2H (8.93 d, 8.12 d, 7.88 m, 7.82 m, 7.73 d, 1.72 s)

LC / MS: m / z = 543 [(M + 1) ^&lt; ^{+ &}

Example  35: Synthesis of Compound 692

(One) Manufacturing example  1: Synthesis of intermediate 35-1

Synthesis was conducted in the same manner as in Example 1 (6), except that 2,5-dibromofuran (2.3 g, 0.010 mol) was added to Intermediate 34-1 (2.0 g, 0.012 mol) g (yield: 70%). (m / z = 263)

(2) Manufacturing example  2: Synthesis of intermediate 35-2

Intermediate 35-2 was synthesized in the same manner as in Example 1 (6) except that triphenylen-2-ylboronic acid (3.4 g, 0.012 mol) was added to Intermediate 35-1 (3.0 g, 0.010 mol) 3.0 g (yield: 73%). (M / z = 410)

(3) Manufacturing example  3: Synthesis of intermediate 35-3

2.3 g (0.007 mol) of intermediate <35-3> were synthesized in the same manner as in Example 1 (2) except that methyl 2-bromobenzoate (1.5 g, 0.007 mol) (Yield: 65%). (M / z = 544)

(4) Manufacturing example  4: Synthesis of intermediate 35-4

Intermediate 35-3 (3.0 g, 0.009 mol) was added thereto, and 3.1 g (yield 70%) of <Intermediate 35-4> was obtained in the same manner as in Example 1- = 544)

(5) Manufacturing example  5: Synthesis of compound 692

3.1 g (yield 71%) of Compound 692 was obtained by the same method as in Example 1- (4), except that Intermediate 35-4 (3.0 g, 0.009 mol) was added.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.61 / d, 7.41 / m, 7.40 / m, 7.37 / m, 7.30 / d, 7.26 / d , 7.14 / m) 2H (8.93 d, 8.12 d, 7.88 m, 7.82 m, 7.07 d, 1.72 s)

LC / MS: m / z = 527 [(M + 1) ^&lt; ^{+ &}

Example  36: Synthesis of Compound 693

(One) Manufacturing example  1: Synthesis of Intermediate 36-1

Dibromochloromethane (2.3 g, 0.011 mol) was added to 3,6-dibromobenzene-1,2-diamine (3.0 g, 0.011 mol) and the reaction was conducted in the same manner as in Example 25- 1> 1.4 g (yield 41%). (M / z = 312)

(2) Manufacturing example  2: Synthesis of intermediate 36-2

The intermediate 36-1 (3.0 g, 0.010 mol) was synthesized in the same manner as in Example 1 (2) except that 1-bromo-2-tert-butylbenzene (2.1 g, 0.010 mol) -2> 1.9 g (yield: 50%). (M / z = 386)

(3) Manufacturing example  3: Synthesis of intermediate 36-3

2.1 g (intermediate 36-3) was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.2 g, 0.010 mol) was added to Intermediate 36-2 (3.0 g, 0.0008 mol) Yield: 60%). (M / z = 428)

(4) Manufacturing example  4: Synthesis of intermediate 36-4

100 mL of DMF was added to N-bromosuccinimide (1.2 g, 0.007 mol) in Intermediate 36-3 (3.0 g, 0.007 mol), and the mixture was reacted at 20 ° C for 8 hours with stirring. After completion of the reaction H ₂ 0: After phase separation with ethyl acetate and column purification: the (n-Hexane MC) to the intermediate 36-4 to give 1.4 g (40%) (m / z = 507).

(5) Manufacturing example  5: Synthesis of intermediate 36-4 '

Intermediate 36-4 'was synthesized in the same manner as in Example 1 (5) except that bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to Intermediate 36-4 (5.0 g, 0.010 mol) 3.9 g (yield 71%) of the title compound was obtained (m / z = 554)

(6) Manufacturing example  6: Synthesis of intermediate 36-5

Bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to 2-bromo-4,6-diphenyl-1,3,5-triazine (2.5 g, 0.008 mol) (M / z = 359) (yield: 73%). &Lt; / RTI >

(7) Manufacturing example  7: Synthesis of Intermediate 36-6

2.0 g (Compound 693) was synthesized in the same manner as in Example 1 (6), except that 1,4-dibromobenzene (1.6 g, 0.007 mol) was added to Intermediate 36-5 (3.0 g, 0.008 mol) Yield: 73%). (M / z = 388)

(8) Manufacturing example  8: Synthesis of Compound 693

4.3 g (Compound 693) was synthesized in the same manner as in Example 1- (6) except that Intermediate 36-6 (3.1 g, 0.008 mol) was added to Intermediate 36-4 '(5.0 g, 0.009 mol) Yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.26 / m, 6.88 / s, 5.04 / s) 2H (7.85 / d, 7.43 / d, 7.41 / m, 7.33 / m, 7.25 / d, 7.08 / d, 7.05 / m, 6.69 / m, 6.52 / d) 4H (8.28 / d, 7.51 /

LC / MS: m / z = 736 [(M + 1) ^&lt; ^{+ &}

Example  37: Synthesis of Compound 694

(One) Manufacturing example  1: Synthesis of compound 694

The compound obtained in the same manner as in Example 1 (6) was used in place of Intermediate 36-2 (3.0 g, 0.008 mol) and Intermediate 21-5 (4.3 g, 0.010 mol) 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (5.04 / d) 2H (8.52 / d, 7.41 / m, 7.29 / d, 7.08 / d, 7.05 / m, 6.69 / m, 6.52 / d, 6.32 / d) 4H (8.28 / d, 7.51 / m, 1.72 / s)

LC / MS: m / z = 660 [(M + 1) ^&lt; ^{+ &}

Example  38: Synthesis of Compound 695

(One) Manufacturing example  1: Synthesis of Compound 695

(Compound 695) (synthesis amount: 5.3 g, yield: 5.0 g, 0.010 mol) and Intermediate 22-5 (5.1 g, 0.012 mol) 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d, 7.26 / m, 6.88 / s, 5.04 / s) 2H (8.93 / d, 8.12 / d, 7.88 d, 7.02 / d, 7.05 / m, 6.69 / m, 6.52 / d) 4H (7.25 / d, 1.72 / s)

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

Example  39: Synthesis of Compound 696

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

(6.9 g, 0.008 mol) and 1,4-dibromobenzene (1.9 g, 0.008 mol) were added in the same manner as in Example 1-Preparation Example (6), except that dibenzo [b, d] thiophen- 1.9 g (yield: 70%) of Intermediate 39-1 was obtained. (M / z = 339)

(2) Manufacturing example  2: Synthesis of Compound 696

4.0 g (Compound 696) was synthesized in the same manner as in Example 1- (6) except that Intermediate 36-4 '(5.0 g, 0.009 mol) and Intermediate 39-1 (2.7 g, 0.008 mol) Yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 8.41 / d, 8.20 / d, 7.98 / d, 7.58 / m, 7.52 / m, 7.50 / m, 7.26 / m, 6.88 / s , 7.04 / s, 7.04 / s) 2H (7.43 / d, 7.33 / m, 7.08 / d, 7.05 /

LC / MS: m / z = 687 [(M + 1) ^&lt; ^{+ &}

Example  40: Synthesis of Compound 697

(One) Manufacturing example  1: Synthesis of intermediate 40-1

Intermediate 40-1 was synthesized in the same manner as in Example 1- (6) except that Intermediate 36-4 '(5.0 g, 0.009 mol) and 1,4-dibromobenzene (1.9 g, 0.008 mol) 3.4 g (yield: 73%) was obtained. (M / z = 583)

(2) Manufacturing example  2: Synthesis of compound 697

Synthesis was conducted in the same manner as in Example 1 (2), except that Intermediate 40-1 (5.0 g, 0.009 mol) and 9H-carbazole (2.2 g, 0.009 mol) %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.12 / d, 7.94 / d, 7.63 / d, 7.50 / m, 7.33 / m, 7.29 / m, 7.26 / m, 7.25 / m , 6.88 / s, 5.04 / s) 2H (7.79 d, 7.68 d, 7.43 d, 7.33 m, 7.08 d, 7.05 m, 6.69 m, 6.52 d)

LC / MS: m / z = 670 [(M + 1) ^&lt; ^{+ &}

Example  41: Synthesis of compound 698

(One) Manufacturing example  1: Synthesis of Compound 698

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 40-1 (5.0 g, 0.009 mol) and 9-phenyl-9H-carbazol-3-ylboronic acid (3.2 g, 0.011 mol) <Compound 698> 4.9 g (yield: 73%) was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.45 / m, 7.33 / m, 7.26 / m, 7.25 / m , 6.88 / s, 5.04 / s) 2H (7.58 / m, 7.50 / d, 7.43 / d, 7.33 / m, 7.08 / d, 7.05 / / s)

LC / MS: m / z = 746 [(M + 1) ^&lt; ^{+ &}

Example  42: Synthesis of Compound 699

(One) Manufacturing example  1: Synthesis of intermediate 42-1

Synthesis was conducted in the same manner as in Example 1 (6), except that 3-bromo-9H-carbazole (1.8 g, 0.007 mol) was added to Intermediate 42-1 (5.0 g, 0.009 mol) > 2.9 g (yield: 71%). (M / z = 593)

(2) Manufacturing example  2: Synthesis of Compound 699

Synthesis was conducted in the same manner as in Example 1 (6), except that 4-bromo-2,6-diphenylpyridine (2.6 g, 0.008 mol) was added to Intermediate 42-2 (5.0 g, 0.008 mol) (Yield: 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.33 / m, 7.26 / m, 7.25 / m, 6.88 / s D, 7.54 / m, 7.72 / d), 5.04 / s) 2H (7.47 / m, 7.43 / d, 7.33 / m, 7.10 / s, 7.08 / d, 7.05 / / s)

LC / MS: m / z = 824 [(M + 1) ^&lt; ^{+ &}

Example  43: Synthesis of Compound 700

(One) Manufacturing example  1: Synthesis of Compound 700

The same procedure as in Example 1 (6) was repeated except that Intermediate 42-1 (5.0 g, 0.008 mol) and 2-bromo-4,6-diphenyl-1,3,5-triazine (2.6 g, 0.008 mol) To obtain 4.7 g (yield 71%) of < Compound 700 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.94 / d, 7.87 / d, 7.77 / d, 7.69 / d, 7.33 / m, 7.26 / m, 7.25 / m, 6.88 / s, 5.04 / s ), 2H (7.43 / d, 7.41 / m, 7.33 / m, 7.08 / d, 7.05 / m, 6.69 /

LC / MS: m / z = 826 [(M + 1) ^&lt; ^{+ &}

Example  44: Synthesis of Compound 2

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

3-ylboronic acid (2.0 g, 0.012 mol), N- (biphenyl-4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- (M / z = 552) was obtained in the same manner as in Example 1 (6), except that the compound (44)

(2) Manufacturing example  2: Synthesis of intermediate 44-2

Intermediate 44-2 was synthesized in the same manner as in Example 1 (2) except that Intermediate 44-1 (5.0 g, 0.008 mol) and methyl 2-bromobenzoate (2.6 g, 0.012 mol) (Yield: 79%). (M / z = 686)

(3) Manufacturing example  3: Synthesis of intermediate 44-3

Synthesis was conducted in the same manner as in Example 1 (3), except that Intermediate 44-2 (5.0 g, 0.007 mol) was added to obtain 3.6 g (yield 75%) of Intermediate 44-3. M / z = 686)

(4) Manufacturing example  4: Synthesis of compound 2

3.5 g (yield 75%) of <Compound 2> was obtained by the same method as in Example 1- (6), except that Intermediate 44-2 (5.0 g, 0.007 mol) was added.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.40 / m, 7.38 / m, 7.37 / m, 7.36 / s , 7.54 / d, 6.69 / d, 6.72 / d, 7.58 / d) 2H (7.52 / d, 7.51 / / s)

LC / MS: m / z = 669 [(M + 1) ^&lt; ^{+ &}

Example  45: Synthesis of compound 4

(One) Manufacturing example  1: Synthesis of Compound (4)

4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine (5.2 g, 0.010 mol) instead of N- (biphenyl- 4.4 g (yield 70%) of Compound 4 was obtained in the same manner as in <Compound 2> using N- (4-bromophenyl) biphenyl-4-amine (4.8 g, 0.010 mol).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.40 / m, 7.37 / m, 7.36 / s, 7.34 / m, 7.30 / d, 7.26 / d, 7.04 / d) 2H (7.41 / m, 1.72 / s) 4H (7.52 / d, 7.51 / m) 6H (7.54 / d, 6.69 / d)

LC / MS: m / z = 629 [(M + 1) ^&lt; ^{+ &}

Example  46: Synthesis of Compound 11

(One) Manufacturing example  1: Synthesis of Compound 11

Intermediate 46-1 (5.1 g, 0.010 mol) was used in the place of N- (biphenyl-4-yl) -N- (4- bromophenyl) -9,9-dimethyl-9H- ) Was used to obtain Compound (11) (5.4 g, Yield: 72%) in the same manner as in < Compound 2 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.42 / s, 7.40 / m, 7.37 / m, 7.34 / m, 7.30 / d, 7.26 / d, 7.04 / d, 6.49 / s ) 2H (7.87 d, 7.62 d, 7.55 d, 7.38 m, 7.28 m, 6.75 s, 6.58 d, 2.59 s)

LC / MS: m / z = 737 [(M + 1) ^&lt; ^{+ &}

Example  47: Synthesis of Compound 12

(One) Manufacturing example  1: Synthesis of Compound 12

Intermediate 47-1 (5.3 g, 0.010 mol) was used in the place of N- (biphenyl-4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- ), 5.2 g (yield 72%) of <Compound 12> was obtained in the same manner as in <Compound 2>.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.87 / d, 7.84 / d, 7.74 / d, 7.69 / d, 7.64 / d, 7.62 / d, 7.55 / d, 7.49 / d 7.36 / s, 7.34 / m, 7.30 / d, 7.28 / m, 7.26 / d, 7.04 / d, 6.75 / s, 6.58 / d) 2H (7.54 / d, 7.52 / d, 7.51 / m, 6.69 /

LC / MS: m / z = 719 [(M + 1) ^&lt; ^{+ &}

Example  48: Synthesis of Compound 19

(One) Manufacturing example  1: Synthesis of Compound 19

Intermediate 48-1 (5.5 g, 0.010 mol) was used instead of N- (biphenyl-4-yl) -N- (4-bromophenyl) -9,9-dimethyl- ) Was used to obtain 5.3 g (yield 75%) of <Compound 19> by the same method as in <Compound 2>.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.40 / m, 7.37 / m, 7.36 / s, 7.34 / m, 7.26 / d, 7.04 / d, 5.73 / s) 2H (6.25 / s, 1.72 / s) 4H (2.34 / s) 8H (6.98 / d, 6.51 / d)

LC / MS: m / z = 700 [(M + 1) ^&lt; ^{+ &}

Example  49: Synthesis of Compound 34

(One) Manufacturing example  1: Synthesis of Compound 34

Intermediate 49-2 (6.5 g, 0.010 mol) was used in the place of N- (biphenyl-4-yl) -N- (4- bromophenyl) -9,9-dimethyl-9H- ) Was used to obtain 6.0 g (yield 75%) of Compound 34 by the same method as in < Compound 2 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.87 / d, 7.70 / s, 7.62 / d, 7.57 / m, 7.55 / d, 7.44 / m, 7.40 / m, 7.38 / m D, 7.28 / d, 7.04 / d, 6.89 / s, 6.88 / d, 6.75 / s, 6.59 / d, 6.58 / d) (7.54 / d, 7.48 / d, 7.38 / d, 7.37 / d, 6.69 /

LC / MS: m / z = 802 [(M + 1) ^&lt; ^{+ &}

Example  50: Synthesis of Compound 39

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

Intermediate 49-1 (3.0 g, 0.007 mol) was mixed with 4-bromobiphenyl (1.6 g, 0.007 mol) and synthesized in the same manner as in Example 1- Yield: 65%). (M / z = 592)

(2) Manufacturing example  2: Synthesis of intermediate 50-2

Synthesis was conducted in the same manner as in Example 7-Preparation Example (2), except that triisopropyl borate (1.9 g, 0.010 mol) was added to Intermediate 50-1 (5.0 g, 0.008 mol) 70%). (M / z = 557)

(3) Manufacturing example  3: Synthesis of Intermediate 50-3

2-ylboronic acid (3.7 g, 0.016 mol) was added to 2-bromo-3-chloro-1H-indole (3.0 g, 0.013 mol) ) To obtain 3.3 g (yield 75%) of Intermediate 50-3 (m / z = 343)

(4) Manufacturing example  4: Synthesis of intermediate 50-4

Intermediate 50-4 (5.8 g, 0.011 mol) was added to Intermediate 50-3 (3.0 g, 0.009 mol) and the reaction mixture was treated in the same manner as in Example 1- (6) (Yield: 73%). (M / z = 821)

(5) Manufacturing example  5: Synthesis of Compound 39

Intermediate 50-4 (8.2 g, 0.010 mol) was used in the place of N- (biphenyl-4-yl) -N- (4- bromophenyl) -9,9-dimethyl-9H- ) Was used to obtain 5.7 g (yield: 61%) of <Compound 39> by the same method as in <Compound 2>.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.93 / d, 7.77 / s, 7.70 / s, 7.63 / d, 7.62 / d, 7.57 / m, 7.44 / m, 7.40 / m D, 6.75 / d, 6.75 / s, 6.59 / d, 6.58 / d) 2H (7.87 / d, 7.55 / d 7.58 / d, 7.51 / m, 7.48 / d, 7.38 / m, 7.28 /

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

Example  51: Synthesis of Compound 46

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

(2.6 g, 0.008 mol) was added to 2,7-dibromo-9,9-dimethyl-9H-fluorene (3.0 g, 0.008 mol) (M / z = 592) (Intermediate 51-1) (3.4 g, Yield: 71%).

(2) Manufacturing example  2: Synthesis of Compound 46

Intermediate 51-1 (5.9 g, 0.010 mol) was used in the place of N- (biphenyl-4-yl) -N- (4- bromophenyl) -9,9-dimethyl-9H- fluoren- ), 5.3 g (yield: 71%) of Compound 46 was obtained in the same manner as in < Compound 2 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.93 / d, 7.77 / s, 7.63 / d, 7.62 / d, 7.40 / m, 7.37 / m, 7.36 / s, 7.34 / m (7.54 / d, 7.52 / d, 7.51 / m, 6.69 / d, 1.72 / s), 7.30 / d, 7.26 / d, 7.04 / d, 6.75 / s, 6.58 /

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

Example  52: Synthesis of Compound 50

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

2-ylboronic acid (1.9 g, 0.011 mol) was added to 2-bromo-1H-indol-3-ylboronic acid (2.2 g, 0.009 mol) in the same manner as in Example 1- To obtain 1.9 g (yield 73%) of Intermediate 52-1 (m / z = 287)

(2) Manufacturing example  2: Synthesis of intermediate 52-2

N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine (5.2 g, 0.010 mol) (M / z = 678) (yield: 71%) was obtained by the same method as in the production example (6) of Example 1-

(3) Manufacturing example  3: Synthesis of Compound 50

(Yield: 71%) was obtained in the same manner as in < Compound 2 >, using Intermediate 52-2 (6.8 g, 0.010 mol).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.34 / d, 7.99 / d, 7.92 / d, 7.55 / m, 7.41 / m, 7.40 / m, 7.38 / m, 7.37 / m, 7.34 / m 7.50 / d, 7.30 / d, 7.28 / d, 7.26 / d, 7.00 / d, 6.75 / s, 6.58 / d) 2H (8.00 / d, 7.87 / d, 7.59 / / d, 6.69 / d, 1.72 / s)

LC / MS: m / z = 796 [(M + 1) ^&lt; ^{+ &}

Example  53: Synthesis of Compound 54

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

Was synthesized in the same manner as in Example 1 (2) except that biphenyl-4-amine (1.7 g, 0.010 mol) was added to 3,3'-dibromobiphenyl (3.0 g, 0.010 mol) > 2.9 g (yield: 73%). (M / z = 400)

(2) Manufacturing example  2: Synthesis of intermediate 53-2

The intermediate 53-1 (3.6 g, 0.009 mol) was synthesized in the same manner as in Example 1 (2) except that 4-bromo-N, N-diphenylaniline (2.9 g, 0.009 mol) -2> 4.2 g (yield: 73%). (M / z = 643)

(3) Manufacturing example  3: Synthesis of intermediate 53-3

Intermediate 53-2 (5.0 g, 0.008 mol) was synthesized in the same manner as in Example 1 (6) except that 1H-indol-3-ylboronic acid (1.6 g, 0.010 mol) 3> 4.0 g (yield: 73%). (M / z = 679)

(4) Manufacturing example  4: Synthesis of Compound 54

(6.8 g, 0.010 mol) was used in place of Intermediate 53-3 to obtain 5.6 g (Yield: 70%) of Compound 54 by the same procedure as in <Compound 2>.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.70 / s, 7.57 / m, 7.44 / m, 7.41 / m, 7.40 / m, 7.37 / m, 7.36 / s, 7.34 / m 7.51 / d, 7.51 / m, 7.48 / d, 6.81 / m, 6.69 / d , 1.72 / s) 4H (7.20 / m, 6.63 / d, 6.38 / d)

LC / MS: m / z 1 = 797 [(M + 1) ^&lt; ^{+ &}

Example  54: Synthesis of Compound 84

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

(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (3.6 g, 0.010 mol) was added to 1,3,5-tribromobenzene (3.1 g, 0.010 mol) (M / z = 595) (Intermediate 54-1) (4.3 g, yield 73%) was synthesized in the same manner as in Preparation Example (2)

(2) Manufacturing example  2: Synthesis of intermediate 54-2

Intermediate 54-1 (5.0 g, 0.008 mol) was synthesized in the same manner as in Example 1- (6) except that 1H-indol-3-ylboronic acid (1.6 g, 0.010 mol) 2> 3.9 g (yield: 73%). (M / z = 667)

(3) Manufacturing example  3: Synthesis of intermediate 54-3

Intermediate 54-3 was synthesized in the same manner as in Example 1 (2), except that bromobenzene (1.1 g, 0.007 mol) was added to Intermediate 54-2 (5.0 g, 0.007 mol) %). (M / z = 743)

(4) Manufacturing example  4: Synthesis of Compound 84

6.3 g (yield 73%) of Compound 84 was obtained using Intermediate 53-3 (7.4 g, 0.010 mol) using the same method as Compound 2.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.17 / d, 7.99 / d, 7.87 / d, 7.71 / d, 7.62 / d, 7.55 / d, 7.40 / m, 7.38 / m, 7.37 / m 7.58 / d, 7.52 / d, 7.52 / d, 7.04 / d, 6.75 / , 7.50 / d, 7.42 / m, 7.41 / m, 7.36 / s, 6.85 / s, 6.69 /

LC / MS: m / z = 861 [(M + 1) ^&lt; ^{+ &}

Example  55: Synthesis of compound 93

(One) Manufacturing example  1: Synthesis of intermediate 55-1

Was synthesized in the same manner as in Example 1 (2), except that methyl 2-iodobenzoate (4.7 g, 0.018 mol) was added to 3-bromo-5-chloro-1H- indole (3.0 g, 0.013 mol) 3.1 g (yield 65%) of intermediate 55-1 (m / z = 364) was obtained.

(2) Manufacturing example  2: Synthesis of intermediate 55-2

Intermediate 55-1 (3.0 g, 0.008 mol) was used to synthesize 1.7 g (yield: 61%) of Intermediate 55-2 in the same manner as in Example 1 (3) = 340)

(3) Manufacturing example  3: Synthesis of intermediate 55-3

2.2 g (yield 72%) of Intermediate 55-3 was obtained in the same manner as in Example 1 (4), except that Intermediate 55-2 (3.0 g, 0.009 mol) was added. M / z = 346)

(4) Manufacturing example  4: Synthesis of Intermediate 55-4

Intermediate 55-4 was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.3 g, 0.011 mol) was added to Intermediate 55-3 (3.0 g, 0.009 mol) Yield: 60%). (M / z = 343)

(5) Manufacturing example  5: Synthesis of intermediate 55-5

<Intermediate 55-5> 2.7 (4-aminopyrimidin-4-yl) pyridine was synthesized by the same method as in Example 1 (5), except that bis (pinacolato) dibron (2.8 g, 0.011 mol) was added to Intermediate 55-4 g (yield: 69%). (m / z = 435)

(6) Manufacturing example  6: Synthesis of intermediate 55-6

Intermediate 55-6 was synthesized by the same method as in Example 1 (6), except that 1,4-dibromobenzene (1.4 g, 0.006 mol) was added to Intermediate 55-5 (3.0 g, 0.007 mol) g (yield: 69%). (m / z = 464)

(7) Manufacturing example  7: Synthesis of compound 93

(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (2.2 g, 0.006 mol) was added to Intermediate 55-6 (3.0 g, 0.006 mol) (2), 3.3 g (yield: 74%) of Compound 93 was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.63 / s, 7.87 / d, 7.62 / d, 7.55 / d, 7.40 / m, 7.38 / m, 7.37 / m, 7.36 / s, 7.30 / d (7.24 / d, 7.51 / m, 6.69 / d, 1.72 / s)

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

Example  56: Synthesis of compound 110

(One) Manufacturing example  1: Synthesis of intermediate 56-1

Intermediate 56-1 was synthesized by the same method as in Example 1 (2), except that bromobenzene (6.8 g, 0.044 mol) was added to 5-bromobenzene-1,3-diamine (2.0 g, 0.011 mol) 3.9 g (yield: 72%) was obtained. (M / z = 491)

(2) Manufacturing example  2: Synthesis of compound 110

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 56-1 (2.9 g, 0.006 mol) and Intermediate 55-5 (3.0 g, 0.007 mol) 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.63 / d, 7.41 / m, 7.40 / m, 7.37 / m, 7.36 / s, 7.30 / d, 7.26 / d, 7.21 / s, 5.73 / s ) 2H (7.52 / d, 7.51 / m, 6.25 / s, 1.72 / s)

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

Example  57: Synthesis of compound 125

(One) Manufacturing example  1: Synthesis of intermediate 57-1

2.0 g of Intermediate 57-1 was synthesized in the same manner as in Example 1 (6) except that phenyl boronic acid (1.4 g, 0.012 mol) was added to 1,4-dibromonaphthalene (3.0 g, 0.010 mol) (Yield: 72%). (M / z = 283)

(2) Manufacturing example  2: Synthesis of intermediate 57-2

Intermediate 57-1> 2.9 g (0.010 mol) of biphenyl-4-amine was added to Intermediate 57-1 (3.0 g, 0.010 mol) g (yield: 77%). (m / z = 371)

(3) Manufacturing example  3: Synthesis of intermediate 57-3

Intermediate 57-3 was synthesized in the same manner as in Example 1 (6) except that 3,3'-dibromobiphenyl (2.5 g, 0.008 mol) was added to Intermediate 55-5 (3.0 g, 0.008 mol) 3.6 g (yield 75%) of the title compound (m / z = 540)

(4) Manufacturing example  4: Synthesis of Compound 125

Intermediate 57-2 (3.6 g, 0.006 mol) was added to Intermediate 57-3 (3.0 g, 0.007 mol), and the compound was synthesized by the same method as in Example 1- (2) 75%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.49 / d, 8.19 / d, 8.06 / d, 7.93 / d, 7.78 / d, 7.70 / s, 7.59 / d, 7.57 / m, 7.44 / m M, 7.69 / d, 7.72 / d, 7.04 / d, 6.89 / s, 6.88 / d) ) 4H (7.54 / d, 7.52 / d) 6H (7.51 / m)

LC / MS: m / z = 832 [(M + 1) ^&lt; ^{+ &}

Example  58: Synthesis of Compound 132

(One) Manufacturing example  1: Synthesis of Compound 132

4-yl) naphthalen-1-amine (2.7 g, 0.009 mol) was added to Intermediate 57-3 (5.0 g, 0.009 mol) in the same manner as in Example 1- To obtain 5.1 g (yield 75%) of < Compound 132 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.19 / d, 8.02 / d, 7.93 / d, 7.70 / s, 7.58 / d, 7.57 / m, 7.44 / m, 7.40 / m, 7.38 / m D, 7.41 / m, 6.69 / d, 1.72 / s, 7.37 / m, 7.36 / s, 7.30 / d, 7.26 / d, 6.98 / d, 6.89 / d, 6.88 / d, 6.59 / ) 4H (7.54 / d, 7.52 / d, 7.51 / m)

LC / MS: m / z = 755 [(M + 1) ^&lt; ^{+ &}

Example  59: Synthesis of Compound 172

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

(Biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine (3.8 g, 0.008 mol) was added to a solution of 2-bromo-1H-indol- (M / z = 591) was obtained in the same manner as in Example 1 (6), and 3.4 g (yield: 71%) of Intermediate 59-1 was obtained.

(2) Manufacturing example  2: Synthesis of intermediate 59-2

Intermediate 59-2 was synthesized in the same manner as in Example 1- (6), except that phenyl boronic acid (1.6 g, 0.013 mol) was added to Intermediate 59-1 (5.0 g, 0.011 mol) Yield: 72%). (M / z = 588)

(3) Manufacturing example  3: Synthesis of Compound 172

5.0 g (Yield 71%) of <Compound 172> was obtained in the same manner as in <Compound 2> using Intermediate 59-2 (5.9 g, 0.010 mol).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.02 / d, 7.40 / m, 7.37 / m, 7.30 / d, 7.26 / d, 7.00 / d, 6.60 / s) 2H (7.79 / d, 1.72 / s) 3H (7.51 / m) 4H (7.52 / d) 6H (7.54 / d, 7.51 /

LC / MS: m / z = 705 [(M + 1) ^&lt; ^{+ &}

Example  60: Synthesis of Compound 183

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

The same procedure as in Example 1-Preparation Example (2) was repeated except that methyl 2-iodobenzoate (4.2 g, 0.016 mol) was added to 5-chloro-2-iodo-1H- benzo [d] imidazole (3.0 g, To obtain 2.6 g (yield: 58%) of Intermediate 60-1 (m / z = 412)

(2) Manufacturing example  2: Synthesis of intermediate 60-2

1.8 g (yield 64%) of Intermediate 60-2 (3.0 g, 0.007 mol) was obtained in the same manner as in Example 1- (3) = 412)

(3) Manufacturing example  3: Synthesis of intermediate 60-3

1.6 g (51%) of Intermediate 60-3 was obtained in the same manner as in Example 1 (4), except that Intermediate 60-2 (3.0 g, 0.008 mol) was added. M / z = 394)

(4) Manufacturing example  4: Synthesis of intermediate 60-4

Intermediate 60-4 (2.0 g, 0.010 mol) was synthesized in the same manner as in Example 1- (6) except that phenyl boronic acid (1.2 g, 0.010 mol) was added to Intermediate 60-3 Yield: 72%). (M / z = 344)

(5) Manufacturing example  5: Synthesis of intermediate 60-4-1

Synthesis was conducted in the same manner as in Example 1-Preparation Example (5), except that bis (pinacolato) dibron (2.8 g, 0.011 mol) was added to Intermediate 60-4 (3.0 g, 0.009 mol) > 2.8 g (yield: 72%) was obtained. (M / z = 436)

(6) Manufacturing example  6: Synthesis of intermediate 60-5

Synthesis was conducted in the same manner as in Example 1 (6), except that 1,4-dibromobenzene (1.9 g, 0.008 mol) was added to Intermediate 60-4-1 (3.9 g, 0.009 mol) > 2.7 g (yield 72%). (M / z = 465)

(7) Manufacturing example  7: Synthesis of Compound 183

To the intermediate 60-5 (3.0 g, 0.006 mol) was added bis (9,9-dimethyl-9H-fluoren-2-yl) amine (2.6 g, 0.006 mol) Synthesis was conducted in the same manner to obtain 3.5 g (yield 75%) of <Compound 183>.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.74 / s, 7.41 / m, 7.40 / m, 7.37 / m, 7.35 / s, 7.30 / d, 7.26 / d) 2H (8.28 / d, 7.87 7.58 / d, 7.54 / d, 7.51 / m, 7.38 / m, 7.28 / m, 6.75 / s, 6.69 / d, 6.58 / d)

LC / MS: m / z = 787 [(M + 1) ^&lt; ^{+ &}

Example  61: Synthesis of compound 184

(One) Manufacturing example  1: Synthesis of Compound 184

(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (2.2 g, 0.006 mol) was added to Intermediate 60-5 (3.0 g, 0.006 mol) (2) to obtain 3.4 g (yield 77%) of < Compound 184 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.74 / s, 7.62 / d, 7.55 / d, 7.40 / m, 7.38 / m, 7.37 / m, 7.35 / s, 7.30 / d (7.58 / d, 7.51 / m, 6.69 / d, 1.72 / s), 7.28 /

LC / MS: m / z = 746 [(M + 1) ^&lt; ^{+ &}

Example  62: Synthesis of compound 186

(One) Manufacturing example  1: Synthesis of intermediate 62-1

Phenyl boronic acid (1.6 g, 0.013 mol) was added to 4-chloro-2-iodo-1H-benzo [d] imidazole (3.0 g, 0.011 mol) in the same manner as in Example 1- 1.5 g (yield: 61%) of Intermediate 62-1 (m / z = 228) was obtained.

(2) Manufacturing example  2: Synthesis of intermediate 62-2

(2.9 g, 0.011 mol) was added to Intermediate 62-1 (2.5 g, 0.011 mol) and the same procedure as in Example 1 (2) was used to synthesize 3.0 g of Intermediate 62-2 (Yield: 61%). (M / z = 362)

(3) Manufacturing example  3: Synthesis of intermediate 62-3

1.6 g (yield: 64%) of <Intermediate 62-3> was obtained by adding the intermediate 62-2 (2.5 g, 0.007 mol) in the same manner as in Example 1- (3) = 362)

(4) Manufacturing example  4: Synthesis of intermediate 62-4

1.7 g (yield 70%) of Intermediate 62-4 was obtained in the same manner as in Example 1 (4) except that Intermediate 62-3 (2.5 g, 0.007 mol) was added. M / z = 344)

(5) Manufacturing example  5: Synthesis of intermediate 62-5

(Intermediate 62-5) 2.5 (2.5 g, 0.010 mol) was added to Intermediate 62-4 (3.0 g, 0.008 mol) in the same manner as in Example 1- g (yield: 73%). (m / z = 436)

(6) Manufacturing example  6: Synthesis of intermediate 62-6

Intermediate 62-6> 2.1 (4-aminopyridine) was synthesized in the same manner as in Example 1 (6), except that 1,4-dibromobenzene (1.3 g, 0.006 mol) g (yield: 75%). (m / z = 465)

(7) Manufacturing example  7: Synthesis of Compound 186

3.0 g (186) of compound 186 was synthesized in the same manner as in Example 1 (2) except that dibiphenyl-4-ylamine (2.1 g, 0.006 mol) was added to Intermediate 62-6 (3.0 g, 0.006 mol) Yield: 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.67 / d, 7.40 / m, 7.37 / m, 7.30 / d, 7.26 / d) 2H (8.28 / d, 1.72 / s) 3H (7.41 / m) 4H (7.52 / d) 6H (7.54 / d, 7.51 / m, 6.69 / d)

LC / MS: m / z = 706 [(M + 1) ^&lt; ^{+ &}

Example  63: Synthesis of Compound 193

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

Synthesis was conducted in the same manner as in Example 1 (6) except that 1,4-dibromo-2,5-dimethylbenzene (2.2 g, 0.009 mol) was added to Intermediate 60-4-1 (3.0 g, 0.011 mol) 3.2 g (yield: 71%) of Intermediate 63-1 (m / z = 493) was obtained.

(2) Manufacturing example  2: Synthesis of Compound 193

To the intermediate 63-1 (5.0 g, 0.010 mol) was added bis (9,9-dimethyl-9H-fluoren-2-yl) amine (4.0 g, 0.010 mol) Synthesis was conducted in the same manner to obtain 6.3 g (yield 77%) of <Compound 193>.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.74 / s, 7.42 / s, 7.41 / m, 7.40 / m, 7.37 / m, 7.35 / s, 7.30 / d, 7.26 / d, 6.75 / s , 6.49 / s) 2H (8.28 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.51 / m, 7.38 / / s)

LC / MS: m / z = 815 [(M + 1) ^&lt; ^{+ &}

Example  64: Synthesis of compound 194

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

2,6-dibromonaphthalene (2.6 g, 0.009 mol) was added to Intermediate 60-4-1 (3.0 g, 0.011 mol) and synthesized in the same manner as in Example 1-Preparation Example (6) (M / z = 515) was obtained in an amount of 3.4 g (yield: 73%).

(2) Manufacturing example  2: Synthesis of Compound 194

(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (2.9 g, 0.008 mol) was added to Intermediate 64-1 (3.0 g, 0.008 mol) (2) to obtain 3.1 g (yield 80%) of < Compound 194 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.84 / d, 7.74 / s, 7.69 / d, 7.64 / d, 7.62 / d, 7.55 / d, 7.49 / d, 7.46 / s D, 7.54 / d, 7.52 / d, 7.28 / d, 7.75 / d, 7.38 / , 7.41 / m, 6.69 / d) 4H (7.51 / m, 1.72 / s)

LC / MS: m / z = 797 [(M + 1) ^&lt; ^{+ &}

Example  65: Synthesis of Compound 212

(One) Manufacturing example  1: Synthesis of intermediate 65-1

Tert-butylbiphenyl-4-amine (2.5 g, 0.011 mol) was added to 2-bromo-9,9-dimethyl-9H-fluorene (3.0 g, 0.0011 mol) (M / z = 417) of <Intermediate 65-1> (yield: 77%) was obtained by the same method as used

(2) Manufacturing example  2: Synthesis of Compound 212

Synthesis was conducted in the same manner as in Example 1 (2) to give Intermediate 65-1 (4.2 g, 0.010 mol) and Intermediate 63-1 (5.0 g, 0.0010 mol) 74%). (M / z = 417)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.74 / s, 7.62 / d, 7.55 / d, 7.42 / s, 7.41 / m, 7.40 / m, 7.38 / m, 7.37 / m 7.58 / d, 7.58 / d, 7.38 / d, 7.38 / d, 7.28 / , 6.69 / d, 2.59 / s) 3H (1.35 / s) 4H (1.72 / s)

LC / MS: m / z = 831 [(M + 1) ^&lt; ^{+ &}

Example  66: Synthesis of compound 215

(One) Manufacturing example  1: Synthesis of intermediate 66-1

(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (3.6 g, 0.010 mol) was added to 3,3'-dibromobiphenyl (3.0 g, 0.0010 mol) (M / z = 592) (4.4 g, yield 75%) was synthesized in the same manner as in Preparation Example (2)

(2) Manufacturing example  2: Synthesis of Compound 215

Synthesis was conducted in the same manner as in Example 1 (2), except that Intermediate 66-1 (5.3 g, 0.009 mol) was added to Intermediate 60-4-1 (3.0 g, 0.011 mol) (Yield: 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.99 / d, 7.87 / d, 7.70 / s, 7.62 / d, 7.57 / m, 7.55 / d, 7.47 / d, 7.44 / m, 7.40 / m , 7.38 / m, 7.30 / d, 7.28 / m, 7.26 / d, 6.89 / s, 6.88 / d, 6.75 / d, 6.59 / d, 6.58 / , 7.52 / d, 7.48 / d, 7.41 / m, 6.69 / d) 4H (7.51 / m, 1.72 / s)

LC / MS: m / z = 823 [(M + 1) ^&lt; ^{+ &}

Example  67: Synthesis of Compound 276

(One) Manufacturing example  1: Synthesis of intermediate 67-1

4-aminophenylboronic acid (1.5 g, 0.011 mol) was added to Intermediate 55-3 (3.0 g, 0.009 mol), and the title compound was synthesized in the same manner as in Example 1- (M / z = 358) (yield: 63%).

(2) Manufacturing example  2: Synthesis of intermediate 67-2

Intermediate 67-2> 3.1 g (Yield 77%) was obtained according to the same method as that employed for the preparation of Example 1- (2) with the introduction of bromobenzene (2.6 g, 0.016 mol) into Intermediate 67-1 (3.0 g, 0.008 mol) %). (M / z = 511)

(3) Manufacturing example  3: Synthesis of intermediate 67-3

Bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to N- (biphenyl-4-yl) -N- (4- bromophenyl) -9,9-dimethyl-9H- ) Was synthesized in the same manner as in Example 1 (5) to give 3.9 g (yield: 70%) of Intermediate 67-3 (m / z = 563)

(4) Manufacturing example  4: Synthesis of Compound 276

Synthesis was conducted in the same manner as in Example 1- (6) to obtain Intermediate 67-2 (5.0 g, 0.010 mol) and Intermediate 67-3 (6.8 g, 0.012 mol) 68%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.63 / s, 7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.40 / m, 7.38 / m, 7.37 / m, 7.36 / s (7.52 / d, 7.51 / m, 6.81 / m) 4H (7.20 / m, 6.63 / d, 1.72 / s) 6H (7.54 / d, 6.69 / d)

LC / MS: m / z = 913 [(M + 1) ^&lt; ^{+ &}

Example  68: Synthesis of Compound 281

(One) Manufacturing example  1: Synthesis of Compound 281

6.4 g (Yield: 71%) of Compound 281 was obtained by using the same method as Compound 2 with the intermediate 54-2 (6.7 g, 0.010 mol).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.38 / m, 7.28 / m, 7.06 / s, 6.75 / s, 6.58 / d 7.36 / s, 7.34 / m, 7.30 / d, 7.26 / d, 7.04 / d, 6.85 / s (7.99 / d, 7.54 / d, 7.52 / d, 7.51 / , 6.69 (d) 6H (1.72 / s)

LC / MS: m / z = 901 [(M + 1) ^&lt; ^{+ &}

Example  69: Synthesis of compound 283

(One) Manufacturing example  1: Synthesis of compound 283

Synthesis was conducted in the same manner as in Example 1-Preparation Example (6), except that Intermediate 48-1 (4.9 g, 0.009 mol) was added to Intermediate 55-1 (5.0 g, 0.011 mol) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.63 / s, 7.41 / m, 7.40 / m, 7.37 / m, 7.36 / s, 7.30 / d, 7.26 / d, 7.21 / s, 5.73 / s ) 2H (7.52 / d, 7.51 / m, 6.25 / s, 1.72 / s)

LC / MS: m / z = 777 [(M + 1) ^&lt; ^{+ &}

Example  70: Synthesis of compound 288

(One) Manufacturing example  1: Synthesis of Compound 288

(2.7 g, 0.005 mol) was added to Intermediate 55-5 (5.0 g, 0.011 mol), and the compound was synthesized in the same manner as in Example 1- (6) 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.63 / s, 7.87 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.28 / m, 7.06 / s, 6.75 / s, 6.58 / d ) 2H (7.54 / d, 7.40 / m, 7.37 / m, 7.36 / s, 7.30 / d, 7.26 / d, 7.21 / s, 6.85 / s, 6.69 / , 7.51 / m, 1.72 / s)

LC / MS: m / z = 1053 [(M + 1) ^&lt; ^{+ &}

Example  71: Synthesis of compound 295

(One) Manufacturing example  1: Synthesis of intermediate 71-1

Synthesis was carried out in the same manner as in Example 1 (2) except that 9,9-dimethyl-9H-fluoren-2-amine (1.3 g, 0.006 mol) was added to Intermediate 55-6 (3.0 g, 0.006 mol) 2.6 g (yield: 74%) of Intermediate 71-1 (m / z = 592) was obtained.

(2) Manufacturing example  2: Synthesis of intermediate 71-2

Synthesis was conducted in the same manner as in Example 1 (2) except that 1,4-dibromobenzene (1.9 g, 0.008 mol) was added to Intermediate 71-1 (5.0 g, 0.008 mol) g (yield: 74%). (m / z = 712)

(3) Manufacturing example  3: Synthesis of compound 295

Compound 295 (3.7 g, Yield: 70%) was synthesized in the same manner as in Example 1- (6) except that Intermediate 71-2 (5.0 g, 0.007 mol) and phenyl boronic acid %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.40 / m, 7.38 / m, 7.37 / m, 7.30 / d, 7.28 / m 7.56 / d, 7.21 / s, 6.75 / s, 6.58 / d) 2H (7.52 / d, 7.51 /

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

Example  72: Synthesis of compound 298

(One) Manufacturing example  1: Synthesis of intermediate 72-1

(6) was prepared by adding 1-phenyl-6,10b-dihydropyrrolo [2,3,4-kl] acridine (3.0 g, 0.011 mol) and 1,4- dibromobenzene (2.6 g, 0.011 mol) (M / z = 437) (intermediate 72-1) (yield: 72%).

(2) Manufacturing example  2: Synthesis of compound 298

To a solution of the intermediate 72-1 (3.0 g, 0.007 mol) and N- (biphenyl-4-yl) -9,9-dimethyl-9H- fluoren- (6), 3.6 g (yield 72%) of Compound 298 was obtained.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.62 / s, 7.55 / d, 7.41 / m, 7.38 / m, 7.28 / m, 4.10 / s) 2H (7.51 / m, 1.72 / s) 4H (7.94 / d, 7.01 / m, 6.38 / m) 5H (7.52 / d)

LC / MS: m / z = 718 [(M + 1) ^&lt; ^{+ &}

Example  73: Synthesis of compound 302

(One) Manufacturing example  1: Synthesis of intermediate 73-1

Was synthesized in the same manner as in Example 1 (2) to give methyl 2-iodobenzoate (4.7 g, 0.018 mol) in the presence of 2-iodo-3H-indole (3.0 g, 0.012 mol) > 3.1 g (yield: 68%). (M / z = 377)

(2) Manufacturing example  2: Synthesis of Intermediate 73-2

1.8 g (yield: 61%) of Intermediate 73-2 (3.0 g, 0.008 mol) was synthesized in the same manner as in Example 1- (3) = 377)

(3) Manufacturing example  3: Synthesis of Intermediate 73-3

2.0 g (yield 70%) of Intermediate 73-3 was obtained in the same manner as in Example 1- (4), except that Intermediate 73-2 (3.0 g, 0.008 mol) = 359)

(4) Manufacturing example  4: Synthesis of Compound 302

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 73-3 (3.0 g, 0.008 mol) and Intermediate 67-3 (4.8 g, 0.010 mol) 75%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.62 / s, 7.58 / d, 7.55 / d, 7.38 / m, 7.28 / m) 2H (7.54 / d, 7.52 / d, 7.51 / m) 4H (7.30 / d, 7.20 / m, 6.69 / d, 6.68 / d, 1.72 / s)

LC / MS: m / z = 669 [(M + 1) ^&lt; ^{+ &}

Example  74: Synthesis of Compound 306

(One) Manufacturing example  1: Synthesis of intermediate 74-1

4-bromo-3-vinylpyridine (1.8 g, 0.010 mol) was added to 2-bromo-6-chloroaniline (2.0 g, 0.010 mol) 74-1> (yield: 41%). (M / z = 244)

(2) Manufacturing example  2: Synthesis of intermediate 74-2

(E) -1,2-dibromoethene (2.2 g, 0.012 mol) was added to Intermediate 74-1 (3.0 g, 0.012 mol) to obtain Intermediate 74 -2> 1.6 g (yield 50%). (M / z = 268)

(3) Manufacturing example  3: Synthesis of Compound 306

This compound was synthesized in the same manner as in Example 1- (6), except that Intermediate 74-2 (3.0 g, 0.011 mol) and Intermediate 67-3 (6.3 g, 0.013 mol) 64%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.43 / d, 8.41 / s, 7.99 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.38 / m, 7.36 / s (7.54 / d, 6.69 / d, 1.72 / s), 7.34 / m, 7.30 / d, 7.28 / m, 7.04 / d, 6.75 / s, 6.58 /

LC / MS: m / z = 670 [(M + 1) ^&lt; ^{+ &}

Example  75: Synthesis of Compound 307

(One) Manufacturing example  1: Synthesis of intermediate 75-1

1,2-dibromobenzene (2.6 g, 0.011 mol) was added to 3-bromobenzene-1,2-diamine (2.0 g, 0.011 mol) (Yield: 71%) of the title compound (m / z = 261)

(2) Manufacturing example  2: Synthesis of intermediate 75-2

(E) -1,2-dibromoethene (2.0 g, 0.011 mol) was added to Intermediate 75-1 (3.0 g, 0.011 mol) to obtain Intermediate 75 -2> 1.6 g (yield: 50%). (M / z = 285)

(3) Manufacturing example  3: Synthesis of Intermediate 75-3

Intermediate 75-3 (2.9 g, yield 74%) was obtained as a white solid from Intermediate 75-2 (3.0 g, 0.011 mol) and bromobenzene (1.7 g, 0.011 mol) %). (M / z = 361)

(4) Manufacturing example  4: Synthesis of intermediate 75-4

Was used in the same manner as in Example 1 (2) except that 1,4-dibromobenzene (2.4 g, 0.010 mol) and bis (9,9-dimethyl-9H- fluoren- (M / z = 556) of <Intermediate 75-3-1> (yield: 74%).

(5) Manufacturing example  5: Synthesis of intermediate 75-4

Intermediate 75-3-1 (5.0 g, 0.009 mol) and bis (pinacolato) dibron (2.8 g, 0.011 mol) were added to the reaction mixture to obtain Intermediate 75-4 > 3.9 g (yield: 71%). (M / z = 603)

(5) Manufacturing example  5: Synthesis of Compound 307

<Intermediate 75-4> was synthesized in the same manner as in Example 1- (6), except that Intermediate 75-3 (3.0 g, 0.008 mol) and Intermediate 75-4 (5.2 g, 0.010 mol) (Yield: 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (6.81 / m) 2H (7.87 / d, 7.62 / d, 7.55 / d, 7.54 / d, 7.38 / m, 7.28 / m, 6.75 / s, 6.69 / d, 6.58 / d) 4H (7.20 / m, 6.81 / m, 6.63 / d, 1.72 / s)

LC / MS: m / z = 758 [(M + 1) ^&lt; ^{+ &}

Example  76: Synthesis of Compound 310

(One) Manufacturing example  1: Synthesis of intermediate 76-1

(2.9 g, 0.013 mol) was added to 2-bromopyrazine (2.0 g, 0.013 mol) in the same manner as in Example 1-Preparation Example (2) > 2.4 g (yield: 59%). (M / z = 308)

(2) Manufacturing example  2: Synthesis of intermediate 76-2

2.0 g (yield: 64%) of <Intermediate 76-2> was obtained by the same method as employed in the preparation example (3) of Example 1, with the intermediate 76-1 (3.0 g, 0.010 mol) = 308)

(3) Manufacturing example  3: Synthesis of intermediate 76-3

2.0 g (yield 70%) of Intermediate 76-3 was obtained in the same manner as in Example 1 (4) except that Intermediate 76-2 (3.0 g, 0.010 mol) was added. M / z = 290)

(4) Manufacturing example  4: Synthesis of intermediate 76-4

Synthesis was conducted in the same manner as in Example 1 (2), except that 1,1-dibromoethene (1.8 g, 0.010 mol) was added to Intermediate 33-1 (3.0 g, 0.010 mol) g (yield: 51%). (m / z = 314)

(5) Manufacturing example  5: Synthesis of Compound 310

(4.8 g, 0.010 mol) was added to Intermediate 76-4 (3.0 g, 0.010 mol) in the same manner as in Example 1- (6) 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.58 / d, 8.51 / d, 7.99 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.38 / m, 7.36 / s (7.54 / d, 6.69 / d, 1.72 / s), 7.34 m, 7.28 m, 7.04 d, 6.75 s, 6.58 d)

LC / MS: m / z = 671 [(M + 1) ^&lt; ^{+ &}

Example  77: Synthesis of Compound 311

(One) Manufacturing example  1: Synthesis of intermediate 77-1

Synthesis was conducted in the same manner as in Example 1 (2), except that 1,2,3-tribromobenzene (3.1 g, 0.010 mol) was added to 2-amino-phenol (2.0 g, 0.010 mol) 1> 1.1 g (yield: 41%). (M / z = 262)

(2) Manufacturing example  2: Synthesis of Intermediate 77-2

Synthesis was conducted in the same manner as in Example 1 (2), except that 1,2-dibromoethene (1.9 g, 0.0011 mol) was added to Intermediate 77-1 (3.0 g, 0.011 mol) g (yield: 51%). (m / z = 286)

(3) Manufacturing example  3: Synthesis of Compound 311

Synthesis was conducted in the same manner as in Example 1- (6), except that Intermediate 67-3 (4.8 g, 0.010 mol) was added to Intermediate 77-2 (3.0 g, 0.010 mol) 70%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.89 / d, 7.87 / d, 7.62 / d, 7.58 / d, 7.55 / d, 7.41 / m, 7.36 / s, 7.30 / m, 7.28 / m (7.54 / d, 6.69 / d), 7.14 / d, 6.88 / d, 6.75 / s, 6.58 /

LC / MS: m / z = 643 [(M + 1) ^&lt; ^{+ &}

Example  78: Synthesis of Compound 312

(One) Manufacturing example  1: Synthesis of intermediate 78-1

Synthesis was conducted in the same manner as in Example 1 (2), except that 1,2,3-tribromobenzene (3.1 g, 0.010 mol) was added to 2-amino-benzenethiol (2.0 g, 0.010 mol) 1> 1.2 g (yield: 43%). (M / z = 278)

(2) Manufacturing example  2: Synthesis of intermediate 78-2

Synthesis was conducted in the same manner as in Example 1 (2), except that 1,2-dibromoethene (1.7 g, 0.0010 mol) was added to Intermediate 78-1 (3.0 g, 0.010 mol) g (yield: 51%). (m / z = 302)

(3) Manufacturing example  3: Synthesis of Compound 312

Synthesis was conducted in the same manner as in Example 1- (6) to obtain Intermediate 67-3 (4.8 g, 0.010 mol) and Intermediate 78-2 (3.0 g, 0.010 mol) 74%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.91 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.42 / d, 7.41 / d, 7.41 / m, 7.38 / m, 7.36 / s (7.52 / d, 7.51 / m, 1.72 / s) 4H (7.54 / d, 6.69 / d), 7.32 / m, 7.28 / m, 7.25 / / d)

LC / MS: m / z = 659 [(M + 1) ^&lt; ^{+ &}

Example  79: Synthesis of Compound 313

(One) Manufacturing example  1: Synthesis of intermediate 79-1

(2.9 g, 0.013 mol) of methyl 2-amino-3-bromobenzoate was added to 3-bromopyridine (2.0 g, 0.013 mol) > 1.8 g (yield: 45%). (M / z = 307)

(2) Manufacturing example  2: Synthesis of intermediate 79-2

1.8 g (yield: 60%) of <Intermediate 79-2> was obtained in the same manner as in Example 1- (3) except that Intermediate 79-1 (3.0 g, 0.010 mol) = 307)

(3) Manufacturing example  3: Synthesis of intermediate 79-3

2.0 g (yield 70%) of <Intermediate 79-3> was obtained by the same method as in Example 1- (3) except that Intermediate 79-2 (3.0 g, 0.010 mol) = 289)

(4) Manufacturing example  4: Synthesis of intermediate 79-4

Intermediate 79-4 was synthesized by the same method as in the preparation example (2) of Example 1, except that 1,1-dibromoethene (1.8 g, 0.010 mol) was added to Intermediate 79-3 (3.0 g, 0.010 mol) g (yield: 54%). (m / z = 313)

(5) Manufacturing example  5: Synthesis of Compound 313

Synthesis was conducted in the same manner as in Example 1- (6), except that Intermediate 67-3 (4.8 g, 0.010 mol) was added to Intermediate 79-4 (3.0 g, 0.010 mol) 66%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.60 / s, 8.10 / d, 7.99 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.38 / m, 7.36 / s (7.54 / d, 6.69 / d, 1.72 / s), 7.34 / m, 7.28 / m, 7.04 / d, 6.97 / d, 6.75 / s, 6.58 /

LC / MS: m / z = 670 [(M + 1) ^&lt; ^{+ &}

Example  80: Synthesis of Compound 314

(One) Manufacturing example  1: Synthesis of intermediate 80-1

(2.9 g, 0.013 mol) was added to 3-bromopyridine (2.0 g, 0.013 mol) in the same manner as in Example 1 (2) to obtain Intermediate 80-1 > 1.7 g (yield: 41%). (M / z = 307)

(2) Manufacturing example  2: Synthesis of intermediate 80-2

1.6 g (yield 53%) of Intermediate 80-2 (3.0 g, 0.010 mol) was obtained by the same method as in Example 1- (3) = 307)

(3) Manufacturing example  3: Synthesis of Intermediate 80-3

1.8 g (yield: 61%) of Intermediate 80-3 was obtained in the same manner as in Example 1 (4), except that Intermediate 80-2 (3.0 g, 0.010 mol) = 289)

(4) Manufacturing example  4: Synthesis of Intermediate 80-4

Intermediate 80-4> 1.4 (1) Synthesis was conducted in the same manner as in Example 1 (2) except that 1,1-dibromoethene (1.8 g, 0.010 mol) was added to Intermediate 80-3 (3.0 g, 0.010 mol) g (yield: 44%). (m / z = 313)

(5) Manufacturing example  5: Synthesis of Compound 314

Synthesis was conducted in the same manner as in Example 1 (6) to give Intermediate 67-3 (4.8 g, 0.010 mol) and Intermediate 80-4 (3.0 g, 0.010 mol) 60%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.43 / d, 8.10 / d, 7.99 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.38 / m, 7.36 / s (7.54 / d, 6.69 / d, 1.72 / s), 7.34 m, 7.28 m, 7.20 m, 7.04 d, 6.75 s, 6.58 d)

LC / MS: m / z = 670 [(M + 1) ^&lt; ^{+ &}

Example  81: Synthesis of Compound 315

(One) Manufacturing example  1: Synthesis of intermediate 81-1

The title compound was synthesized in the same manner as in Example 1 (6), except that phenyl boronic acid (1.4 g, 0.012 mol) was added to 2-bromo-1H-indol-3-ylboronic acid (2.4 g, 0.010 mol) 1.7 g (yield: 72%) of Intermediate 81-1 was obtained. (M / z = 237)

(2) Manufacturing example  2: Synthesis of Intermediate 81-2

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 67-3 (7.9 g, 0.014 mol) was added to 2,5-dibromothiophene (3.0 g, 0.012 mol) g (yield 70%). (m / z = 598)

(3) Manufacturing example  3: Synthesis of intermediate 81-3

Intermediate 81-3 (5.0 g, 0.011 mol) was added to Intermediate 81-1 (3.0 g, 0.013 mol) to obtain Intermediate 81-2 (7.8 g, 0.011 mol) (Yield: 64%). (M / z = 710)

(4) Manufacturing example  4: Synthesis of Compound 315

6.2 g (yield 75%) of <compound 315> was obtained in the same manner as in <compound 2> using Intermediate 81-3 (7.1 g, 0.010 mol).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.37 / d, 7.87 / d, 7.55 / d, 7.62 / d, 7.40 / m, 7.38 / m, 7.37 / m, 7.30 / d, 7.28 / m D, 7.57 / d, 7.17 / m, 7.00 / d, 6.75 / s, 6.58 / d) 2H (7.73 / d, 7.41 / / s)

LC / MS: m / z = 828 [(M + 1) ^&lt; ^{+ &}

Example  82: Synthesis of Compound 316

(One) Manufacturing example  1: Synthesis of intermediate 82-1

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 67-3 (7.9 g, 0.014 mol) was added to 2,5-dibromofuran (3.0 g, 0.012 mol) g (yield: 65%). (m / z = 582)

(2) Manufacturing example  2: Synthesis of intermediate 82-2

Intermediate 82-1 (6.8 g, 0.011 mol) was added to Intermediate 81-1 (3.0 g, 0.013 mol), and the reaction was conducted in the same manner as in Example 1- (6) (Yield: 60%). (M / z = 694)

(3) Manufacturing example  3: Synthesis of Compound 316

Using the intermediate 82-2 (6.9 g, 0.010 mol), 5.8 g (Yield 71%) of <Compound 316> was obtained in the same manner as in <Compound 2>.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.37 / d, 7.87 / d, 7.55 / d, 7.62 / d, 7.40 / m, 7.38 / m, 7.37 / m, 7.30 / d, 7.28 / m M, 7.07 / d) 4H (7.54 / d, 7.52 / d, 7.51 / m, 6.69 / d, 1.72 / s)

LC / MS: m / z = 812 [(M + 1) ^&lt; ^{+ &}

Example  83: Synthesis of Compound 317

(One) Manufacturing example  1: Synthesis of Compound 317

(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (3.2 g, 0.009 mol) was added to Intermediate 40-1 (3.0 g, 0.009 mol) (2) to obtain 6.0 g (yield: 77%) of < Compound 317 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.87 / d, 7.83 / m, 7.62 / d, 7.55 / d, 7.41 / m, 7.38 / m, 7.28 / m, 7.08 / d, 7.05 / m (7.54 / d, 7.51 / m, 6.69 / d, 1.72 / s), 6.75 / s, 6.58 / d, 6.52 /

LC / MS: m / z = 865 [(M + 1) ^&lt; ^{+ &}

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

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

Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and Alq ₃ was deposited thereon to form an electron transporting layer of 40 nm. Lithium fluoride To form a 1 nm electron injection layer. Aluminum was deposited on the electron injection layer to form a 120 nm negative electrode, thereby fabricating an organic electroluminescent device.

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

device Example  2 to 43

An organic electroluminescent device of each of the device embodiments 2 to 43 was fabricated in the same manner as in the device example 1, except that the compound described in [Table 1] was used in place of the compound 1 described above.

device Comparative Example  One

The organic light emitting diode device for Comparative Example 1 was fabricated in the same manner except that CBP, which is generally used as a phosphorescent host material, was used instead of the compound 1 produced by the invention in the device structure of the embodiment.

Device Example  44: Compound 44 With hole transport material  So Organic electroluminescent device  Produce

Compound 44 was deposited on ITO-coated glass substrate to form a 120 nm hole transport layer. Subsequently, Ir (ppy) ₃ was used as a dopant to deposit CBP at 0.1 nm / sec and Ir (ppy) ₃ And the Ir (ppy) ₃ was doped so that the deposition rate ratio was 9% to form a light emitting layer with a thickness of 30 nm on the hole transport layer.

Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and Alq ₃ was deposited thereon to form an electron transporting layer of 40 nm. Lithium fluoride To form a 1 nm electron injection layer. Aluminum was deposited on the electron injection layer to form a 120 nm negative electrode, thereby fabricating an organic electroluminescent device.

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

device Example  45 to 83

Organic electroluminescent devices of Device Examples 45 to 83 were fabricated in the same manner as in Example 44 except that the compound described in [Table 2] was used instead of Compound 44.

device Comparative Example  2

The organic light emitting diode device for Comparative Example 2 was fabricated in the same manner except that NPB, which is generally used as a hole transport material, was used instead of the compound 1 produced by the invention in the device structure of the embodiment.

The structures of Ir (ppy) ₃ , CBP and NPB used in the above are as follows.

[Table 1]

[Table 2]

Measurement of driving voltage and luminous efficiency

After fixing the organic light emitting device (substrate size: 25 × 25 mm 2 / deposition area: 2 × 2 mm 2) to the IVL measurement set (CS-2000 + jig + IVL program), the current was increased by 1 mA / The driving voltage and the luminous efficiency were measured at a luminance of 1000 cd / m 2 by measuring the luminance (cd / m 2), the driving voltage (V), the current density (A / ] And [Table 2].

According to [Table 1] and [Table 2], when the compound for an organic electroluminescent device according to the present invention is used as a host material or a hole transport material of the light emitting layer of an organic electroluminescent device, conventional CBP (host material), NPB Hole transporting material), the driving voltage is lowered and the luminous efficiency is increased.

Claims (12)

An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]

In the above formula (1)
X ₁ to X ₁₀ are each independently N or CR ₁ and X ₁₁ is a single bond or is selected from CR ₂ R ₃ , CR ₄ , NR ₅ , PR ₆ , SiR ₇ R ₈ , O and S,
Each of R ₁ to R ₈ is independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 alkylthio group, a substituted or unsubstituted C1 to C30 arylthio group, An unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted C3 to C30 cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, A substituted or unsubstituted aryl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group, an amino group, a thiol group, a cyano group, a hydroxyl group, a nitro group and a halogen group,
The adjacent substituents of R ₁ to R ₈ may be connected to form a single alicyclic or aromatic ring or polycyclic ring. The carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may be substituted with N, S and O Which may be substituted with any one or more hetero atoms selected,
Each of R ₁ to R ₈ may be further substituted with at least one substituent, and the at least one substituent may be one selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, A halogenated alkyl group, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, An aryl group or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, An alkylsilyl group of 1 to 24 carbon atoms, an arylsilyl group of 1 to 24 carbon atoms, and an aryloxy group of 1 to 24 carbon atoms. The method according to claim 1,
The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following Formulas (2) to (17):

In the above Chemical Formulas 2 to 17,
X ₁ to X ₁₁ are the same as defined in the above formula (1), and each of the substituents of X ₁ to X ₁₁ is linked to adjacent substituents to form a monocyclic or polycyclic ring of alicyclic or aromatic And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S and O. The method according to claim 1,
At least one of X ₂ to X ₆ is CR ₃ , and * -R ₃ is represented by the following formula 1:
[Structural formula 1]

In the structural formula 1,
L ₁ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2 to C50 heteroarylene group in which one or more substituted or unsubstituted C 3 -C 30 cycloalkyl is fused,
n is an integer of 0 to 4, and when n is 2 or more, a plurality of L &lt; ₁ &gt; s are the same as or different from each other,
Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 50 carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C2 to C50 heteroaryl group in which one or more ring-opened cycloalkyls having 3 to 30 carbon atoms is fused,
Ar ₁ and Ar ₂ may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may be N, S, O, &lt; / RTI &gt;&lt; RTI ID = 0.0 &gt;
p is an integer of 0 to 3, and when p is 2 or more, a plurality of * - () may be the same or different from each other,
Wherein L _1, Ar ₁ and Ar ₂ each may be further substituted with one or more substituents, the one or more substituents are deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, having a carbon number of 1 A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, An alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms. The method according to claim 1,
Wherein at least one of X ₂ to X ₁₀ is CR ₃ , and * -R ₃ is represented by the following formula 2:
[Structural formula 2]

In the above formula 2,
L ₂ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2 to C50 heteroarylene group in which one or more substituted or unsubstituted C 3 -C 30 cycloalkyl is fused,
m is an integer of 0 to 4, and when m is 2 or more, a plurality of L ₂ are the same or different from each other,
And Ar ₃ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, Substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms in which at least one of 3 to 30 cycloalkyls is fused,
q is an integer of 0 to 3, and when q is 2 or more, a plurality of Ar ₃ may be the same or different,
The plurality of Ar ₃ and substituents thereof may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be N, S, and O &Lt; / RTI &gt; and &lt; RTI ID = 0.0 &gt;
Each of L ₂ and Ar ₃ may be further substituted with one or more substituents each of which may be substituted with one or more substituents selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, A halogenated alkyl group, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, An aryl group or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, An alkylsilyl group of 1 to 24 carbon atoms, an arylsilyl group of 1 to 24 carbon atoms, and an aryloxy group of 1 to 24 carbon atoms. The method according to claim 1,
The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is selected from the following compounds [1] to [324]:

The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the following compounds 325 to 700:

1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic material layers contains an organic light emitting compound of Formula 1 according to any one of claims 1 to 6. 8. The method of claim 7,
Wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously performing electron transport and electron injection, and a light emitting layer, Wherein at least one layer comprises an organic light-emitting compound represented by the above formula (1). 9. The method of claim 8,
Wherein the light emitting layer comprises an organic light emitting compound represented by the following formula (1). 10. The method of claim 9,
The organic electroluminescent compound represented by Formula 1 is used as a host compound in the light emitting layer, and the light emitting layer further includes at least one dopant compound. 9. The method of claim 8,
Wherein the hole transport layer or the layer simultaneously injecting holes and transporting holes comprises an organic light emitting compound represented by the following formula (1). 8. The method of claim 7,
Wherein at least one of the organic light emitting layers emitting red, green or blue light is further included in the organic material layer to emit white light.

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