KR101729373B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic compound and an organic electroluminescent device including the organic compound, wherein the compound according to the present invention is used in an organic compound layer of an organic electroluminescent device, And the like can be improved.

Description

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

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the compound.

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

The luminescent material may be classified into blue, green, and red luminescent materials according to luminescent colors, and yellow and orange luminescent materials necessary to realize better natural colors. A host / dopant system can be used as a luminescent material to increase the luminous efficiency through increase of color purity and energy transfer.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the phosphorescent dopant can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent dopant, studies on the phosphorescent dopant as well as the phosphorescent host have been conducted.

Currently, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. As phosphorescent dopant materials used for the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like are known. As phosphorescent host materials, 4,4-dicarbazolybiphenyl (CBP) is known.

However, since the conventional materials have low glass transition temperature and poor thermal stability, they are not satisfactory in terms of lifetime in organic electroluminescent devices, and still need improvement in terms of luminescent properties.

Japanese Patent Application Laid-Open No. 2001-160489

In order to solve the above problems, it is an object of the present invention to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and improved luminescence properties.

Another object of the present invention is to provide an organic electroluminescent device comprising the organic compound.

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

[Chemical Formula 1]

In Formula 1,

X ₁ is selected from the group consisting of O, S and N (Ar ₁ )

Ar ₁ represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C An aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C of the group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of the C ₆₀ group And an arylamine group of C ₆ to C ₆₀ ,

R ₁ to R ₁₀ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ C ₆₀ groups of the aryl phosphine group, an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of is selected from the group consisting of,

At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ is bonded to each other to form a condensed ring represented by the following formula (2)

(2)

In Formula 2,

The dotted line is a moiety bonded to the above formula (1)

X ₂ is selected from the group consisting of _{O, S, N (R 31} ), C (R 32) (R 33) and _{Si (R 34) (R 35} ),

R ₁₁ to R ₁₄ and R ₃₁ to R ₃₅ each independently represent hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, and selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of,

Wherein Ar _1, R ₁ to R ₁₄ and R ₃₁ to R ₃₅ an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, alkyloxy group, aryloxy group, alkyl silyl group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, an aryl group, an aryl group, _A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, an aryl group having 5 to 60 nuclear atoms a heteroaryl group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ boron alkyl group, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an arylamine C in ₆₀ 1 may be unsubstituted or substituted by at least one substituent, and the substituent may form a condensed ring by combining adjacent tile.

When Ar ₁ , R ₁ to R _14, and R ₃₁ to R ₃₅ are substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a positive electrode, a negative electrode, and at least one organic material layer interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic material layers contains a compound represented by the above formula An organic electroluminescent device is provided.

Since the compound according to the present invention is excellent in heat resistance, carrier transport ability, and light emitting ability, it can be used as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound according to the present invention in the organic material layer can significantly improve aspects such as light emitting performance, driving voltage, lifetime, and efficiency, and thus can be effectively applied to a full color display panel and the like.

Hereinafter, the present invention will be described.

1. Organic compounds

The novel organic compounds according to the present invention can be prepared by reacting dibenzo [b, f] azepine, dibenzo [b, f] oxepine or dibenzo [b, a 5-membered heteroaromatic ring moiety, an indene moiety, or an indole moiety is condensed with thiepine to form a basic skeleton.

The compound represented by Formula 1 of the present invention can control the HOMO and LUMO energy levels according to the type of substituent introduced into the basic skeleton, and can have a wide band gap and a high carrier transporting property. For example, the compound represented by Formula 1 may have an electron-withdrawing group (EWG) such as a nitrogen-containing heterocycle (e.g., pyridine group, pyrimidine group, triazine group, etc.) , Since the entire molecule has a bipolar characteristic, the bonding force between holes and electrons can be increased. Since the compound represented by the formula (1) introduced with EWG is excellent in carrier transporting property and light emitting property, it can be used not only as a light emitting layer material of an organic electroluminescence device but also as a carrier transporting layer material.

On the other hand, when a large electron donor (EDG) such as an arylamine group, a carbazole group, a terphenyl group, and a triphenylene group is bonded to the basic skeleton of the compound of Formula 1, injection and transport of holes are smooth The hole injecting / transporting layer or the light emitting auxiliary layer material can be effectively used.

In addition, the compound represented by the formula (1) of the present invention has various substituents, particularly aryl groups and / or heteroaryl groups, introduced into the basic skeleton and the molecular weight of the compound is significantly increased, For example, CBP may have higher thermal stability. Further, the compound represented by the general formula (1) of the present invention is also effective for inhibiting crystallization of the organic material layer.

In addition, the compound represented by the formula (1) of the present invention has an indole moiety having a broad singlet energy level and a high triplet energy level condensed therein, and various substituents are introduced, Can be usefully applied.

Accordingly, when the compound represented by Formula 1 of the present invention is applied to an organic compound layer (specifically, a hole transport layer, a hole injection layer, an electron transport layer, or a light emitting layer) of an organic electroluminescent device, the driving voltage, Can be improved. As a result, the organic light emitting device having improved performance and lifetime characteristics can maximize the performance of the full color organic light emitting panel.

The compound represented by the formula (1) of the present invention may be selected from the group consisting of compounds represented by the following formulas (1a) to (1f).

[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

≪ RTI ID = 0.0 &

[Formula 1e]

(1f)

In the above formulas (1a) to (1f), X ₁ , X ₂ and R ₁ to R ₁₄ are as defined in the above formula (1).

Meanwhile, in the fused ring compound represented by the above formula (2) represented by the combined formula _1, R 1 to R ₁₄ At least one of R < ₇ > to R < ₇ > R < ₁₄ > is preferably represented by the following formula (3), and R < _{7 &} R ₁₀ Is more preferably represented by the following formula (3).

(3)

In Formula 3, L ₁ is selected from the group consisting of a single bond, an arylene group having ₆ to ₆₀ carbon atoms, and a heteroarylene group having 5 to 60 nuclear atoms, * is a moiety bonded to Formula 1,

X ₃ is selected from the group consisting of _{O, S, N (R 31} ), C (R 32) (R 33) and _{Si (R 34) (R 35} ),

R ₂₁ to R ₂₈ and R ₃₁ to R _{35 which} are not connected to L ₁ are each independently hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl , A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, is selected from the group C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine, consisting of,

The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group and arylsilyl group of R ₂₁ to R ₂₈ and R ₃₁ to R ₃₅ , alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, arylene group and heteroarylene group each independently selected from deuterium, halogen, a cyano group of the L _1, a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C of ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ cycloalkyl in the group, a number of nuclear atoms of 3 to 40 aryl , A heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ May be unsubstituted or substituted by one or more substituents selected from the group consisting of aryl amines, and the substituents may be bonded to the adjacent groups can form a condensed ring.

When R ₂₁ to R ₂₈ and R ₃₁ to R ₃₅ are substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.

Here, considering the characteristics of the organic electroluminescent device, it is preferable that L ₁ in Formula 3 is a single bond or a phenylene group, and X ₂ is O or N (R ₃₁ ).

In the compound represented by the formula (1) of the present invention, Ar ₁ and R ₃₁ each independently represent a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a nucleus And a heteroaryl group having 5 to 60 atoms, and more preferably a phenyl group or a substituent represented by the following general formula (4).

[Chemical Formula 4]

In Formula 4,

L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

Each of Z ₁ to Z ₅ is independently N or C (R ₁₅ ), wherein at least one of Z ₁ to Z ₅ is N,

Wherein R ₁₅ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group A C ₆ to C ₆₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine pingi, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₆₀ or aryl silyl, by combining groups of adjacent, may form a condensed ring,

Alkyl group of the R _15, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkoxy A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ arylamine group, aryl boron group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ of the group, substituted by C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₆₀ of It may be unsubstituted. When R ₁₅ is substituted with a plurality of substituents, a plurality of substituents may be the same as or different from each other.

Here, considering the characteristics of the organic electroluminescent device, it is preferable that L ₂ in Formula 4 is a single bond, a phenylene group or a biphenylene group.

Furthermore, Z ₁ to Z ₅ or more than one is C (R ₁₅₎ Then C (R ₁₅₎ when the plurality of the plurality of C (R ₁₅₎ of which may be the same or different from each other.

Specifically, the substituent represented by the formula (4) may be selected from the group consisting of the structures represented by the following formulas A1 to A15.

In the formulas (A1) to (A15), L ₂ and R ₁₅ are the same as defined in the formula (4)

R ₄₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , An arylamine group of C ₆ to C ₆₀ , a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₆₀ or aryl silyl, by combining groups of adjacent, may form a condensed ring,

n is an integer of 1 to 4,

Alkyl group of the R _41, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkoxy A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ arylamine group, aryl boron group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ of the group, substituted by C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₆₀ of It may be unsubstituted. When R ₁₅ is substituted with a plurality of substituents, a plurality of substituents may be the same as or different from each other.

The compounds of the present invention can be represented more specifically by the following formulas, but are not limited thereto.

The alkyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, Pentyl, iso-amyl, hexyl, and the like.

The alkenyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, and the like.

The alkynyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Non-limiting examples thereof include ethynyl, 2-propynyl, and the like.

The cycloalkyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, heterocycloalkyl means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and includes at least one carbon atom in the ring, The three carbons are replaced by a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). Non-limiting examples thereof include morpholine, piperazine, and the like.

The aryl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. At this time, the two or more rings may be attached to each other in a simple attached or condensed form. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.

The heteroaryl in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and includes at least one carbon atom, preferably 1 to 3 carbon atoms in the ring Carbon is replaced by a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). At this time, the heteroaryl may be attached in a form in which two or more rings are attached or condensed to each other, and may further include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.

The alkyloxy in the present invention means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms and may include a linear, branched or cyclic structure have. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

In the present invention, aryloxy means a monovalent functional group represented by R'O-, and R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.

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

The condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

2. Organic electroluminescent device

The present invention relates to an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes at least one compound represented by Formula 1 to provide.

The organic material layer containing the compound represented by Formula 1 may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Preferably, the compound represented by Formula 1 may be included in an organic electroluminescent device as a hole injecting layer, a hole transporting layer, and a light emitting layer material. In this case, the light emitting efficiency, brightness, power efficiency, thermal stability, and device lifetime of the organic electroluminescent device can be improved.

In particular, the compound represented by the general formula (1) of the present invention is preferably a phosphorescent host, a fluorescent host or a dopant of a light emitting layer, and more preferably a phosphorescent host of a light emitting layer.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode sequentially laminated. An electron injection layer may be disposed on the electron transport layer.

Also, the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is interposed between the electrode and the organic layer interface.

In the organic electroluminescent device of the present invention, the organic material layer containing the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that one or more of the organic material layers include the compound represented by Formula 1 have.

For example, the substrate may be a silicon wafer, quartz or glass plate, a metal plate, a plastic film, or the like.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The material used for the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer is not particularly limited as long as it is a conventional material known in the art.

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

[Preparation Example 1] Synthesis of IIC-1

<Step 1> Synthesis of 1- (2-bromophenyl) -1H-indole

2-Bromoiodobenzene (290 g, 1.02 mol), Cu powder (21.7 g, 341 mmol), K ₂ CO ₃ (189 g, 1.37 mol), nitrobenzene (1000 mL) under a nitrogen stream, Were mixed and stirred at 190 占 폚 for 12 hours. After the reaction was terminated, the nitrobenzene was removed, extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 9: 1 (v / v)) to obtain 1- (2-bromophenyl) -1H-indole (103.7 g, yield 56%).

^{1 H-NMR: δ 6.69 (} d, 1H), 7.21 (m, 4H), 7.28 (d, 1H), 7.38 (d, 1H), 7.52 (d, 1H), 7.66 (m, 2H)

<Step 2> Synthesis of 4-bromo-5H-dibenzo [b, f] azepine

1000 g of PPA was added to 1- (2-bromophenyl) -1H-indole (103.7 g, 381 mmol) under a nitrogen stream and stirred for 12 hours. After the reaction was completed, the reaction solution was poured into cold water, stirred and neutralized with aqueous NaOH solution. Then, the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the resulting organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain 4-bromo-5H-dibenzo [b, f] azepine (35.2 g, yield 34% .

^{1 H-NMR: δ 4.21 (} brs, 1H), 6.70 (t, 1H), 6.81 (t, 1H), 6.99 (s, 2H), 7.24 (m, 4H), 8.21 (d, 1H)

Synthesis of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine

(35.2 g, 130 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-dibenzo [b, dioxane (36.1 g, 142 mmol), Pd (dppf) Cl ₂ (11.3 g, 13.0 mmol), KOAc (36.5 g, 388 mmol) and 1,4- ) Were mixed and stirred at 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 4- (4,4,5,5- -1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine (25.6 g, yield 62%).

^{1 H-NMR: δ 1.21 (} s, 12H), 4.23 (brs, 1H), 6.74 (t, 1H), 6.83 (t, 1H), 6.99 (s, 2H), 7.24 (m, 4H), 8.20 ( d, 1 H)

<Step 4> Synthesis of 4- (2-nitrophenyl) -5H-dibenzo [b, f] azepine

(16.2 g, 80.2 mmol), 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine (25.6 g, 80.2 mmol), K 2 CO 3 (33.3 g, 241 mmol) and a mixture of _{THF / H 2 O (200 ml} / 50 ml) , and _{then, Pd (PPh 3) 4 (} 4.63 g, 3 mmol), which was stirred for 12 hours at 80 ° C. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 4- (2-nitrophenyl) -5H-dibenzo [b, f] azepine %).

^{1 H-NMR: δ 4.26 (} brs, 1H), 6.80 (t, 1H), 6.88 (t, 1H), 6.96 (s, 2H), 7.27 (m, 4H), 7.67 (d, 1H), 8.07 ( m, 3 H), 8.22 (d, 1 H)

Step 5 Synthesis of 4- (2-nitrophenyl) -5-phenyl-5H-dibenzo [b, f] azepine

5-dibenzo [b, f] azepine (18.4 g, 58.6 mmol), iodobenzene (7.21 mL, 64.4 mmol), Cu powder (1.86 g, 29.3 mmol), K ₂ CO ₃ (16.2 g, 117 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C for 12 hours. After the reaction was terminated, the nitrobenzene was removed, extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (hexane: EA = 20: 1 (v / v)) to obtain 4- (2-nitrophenyl) -5-phenyl-5H-dibenzo [ g, yield 65%).

^{1 H-NMR: δ 6.71-6.88 (} m, 6H), 6.96 (s, 2H), 7.12-7.23 (m, 6H), 7.67 (t, 1H), 8.03 (m, 3H)

<Step 6> Synthesis of IIC-1

Dibenzo [b, f] azepine (14.9 g, 38.1 mmol), triphenylphosphine (25.0 g, 95.4 mmol), 1,2-dichlorobenzene (150 mL) under nitrogen atmosphere, And the mixture was stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain compound IIC-1 (4.78 g, yield 35%).

^{1 H-NMR: δ 6.68-6.73 (} m, 5H), 6.99 (m, 3H), 7.14-7.20 (m, 4H), 7.34-7.41 (m, 4H), 8.12 (d, 1H), 8.51 (brs , 1H)

[Preparation Example 2] Synthesis of IIC-2 & IIC-3

<Step 1> Synthesis of 1- (3-bromophenyl) -1H-indole

Indole (80 g, 683 mmol), 3-bromoiodobenzene (290 g, 1.02 mol), Cu powder (21.7 g, 341 mmol), K ₂ CO ₃ (189 g, 1.37 mol), nitrobenzene (1000 mL) Were mixed and stirred at 190 占 폚 for 12 hours. After the reaction was completed, nitrobenzene was removed, and the residue was extracted with methylene chloride, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 9: 1 (v / v)) to obtain 1- (3-bromophenyl) -1H-indole (103.7 g, yield 56%).

^{1 H-NMR: δ 6.67 (} d, 1H), 7.24 (m, 4H), 7.25 (d, 1H), 7.43 (d, 1H), 7.50 (d, 1H), 7.63 (m, 2H)

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

1000 g of PPA was added to 1- (3-bromophenyl) -1H-indole (103.7 g, 381 mmol) under a nitrogen stream and stirred for 12 hours. After the reaction was completed, the reaction solution was poured into cold water, stirred and neutralized with aqueous NaOH solution. Then, the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the resulting organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain 35.2 g (yield: 34%) of 3-bromo-5H-dibenzo [b, f] azepine .

^{1 H-NMR: δ 4.18 (} brs, 1H), 6.70 (t, 1H), 6.81 (t, 1H), 6.95 (s, 2H), 7.21 (m, 4H), 8.18 (d, 1H)

Synthesis of 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine

(35.2 g, 130 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-dibenzo [b, dioxane (36.1 g, 142 mmol), Pd (dppf) Cl ₂ (11.3 g, 13.0 mmol), KOAc (36.5 g, 388 mmol) and 1,4- ) Were mixed and stirred at 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 3- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine (25.6 g, yield 62%).

^{1 H-NMR: δ 1.20 (} s, 12H), 4.20 (brs, 1H), 6.71 (t, 1H), 6.80 (t, 1H), 6.98 (s, 2H), 7.22 (m, 4H), 8.20 ( d, 1 H)

<Step 4> Synthesis of 3- (2-nitrophenyl) -5H-dibenzo [b, f] azepine

(16.2 g, 80.2 mmol), 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine (25.6 g, 80.2 mmol), K 2 CO 3 (33.3 g, 241 mmol) and a mixture of _{THF / H 2 O (200 ml} / 50 ml) , and _{then, Pd (PPh 3) 4 (} 4.63 g, 3 mmol), which was stirred for 12 hours at 80 ° C. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then the residue was purified by column chromatography (hexane: EA = 20: 1 (v / v)) to obtain 18.4 g of 3- (2-nitrophenyl) -5H-dibenzo [b, f] azepine %).

^{1 H-NMR: δ 4.22 (} brs, 1H), 6.80 (t, 1H), 6.88 (t, 1H), 6.96 (s, 2H), 7.27 (m, 4H), 7.67 (d, 1H), 8.07 ( m, 3 H), 8.22 (d, 1 H)

Step 5 Synthesis of 3- (2-nitrophenyl) -5-phenyl-5H-dibenzo [b, f] azepine

(18.4 g, 58.6 mmol), iodobenzene (7.21 mL, 64.4 mmol), Cu powder (1.86 g, 29.3 mmol), K ₂ CO ₃ (16.2 g, 117 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C for 12 hours. After the reaction was terminated, the nitrobenzene was removed, extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 3- (2-nitrophenyl) -5-phenyl-5H-dibenzo [b, f] azepine g, yield 65%).

^{1 H-NMR: δ 6.68-6.84 (} m, 6H), 6.98 (s, 2H), 7.15-7.23 (m, 6H), 7.66 (t, 1H), 8.01 (m, 3H)

<Step 6> Synthesis of IIC-2 & IIC-3

Dibenzo [b, f] azepine (14.9 g, 38.1 mmol), triphenylphosphine (25.0 g, 95.4 mmol), 1,2-dichlorobenzene (150 mL) under nitrogen atmosphere, And the mixture was stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain 4.78 g of compound IIC-2 (4.78 g, yield 35% 35%).

Of ^{IIC-2 1 H-NMR:} δ 6.68-6.73 (m, 5H), 6.99 (m, 3H), 7.14-7.20 (m, 3H), 7.34-7.41 (m, 4H), 8.08 (d, 1H) , 8.12 (d, 1 H), 8.50 (brs, 1 H)

Of ^{IIC-3 1 H-NMR:} δ 6.70-6.74 (m, 5H), 6.97 (m, 3H), 7.12-7.20 (m, 3H), 7.38-7.42 (m, 4H), 7.99 (s, 1H) , 8.10 (d, 1 H), 8.53 (brs, 1 H)

[Preparation Example 3] Synthesis of IIC-4

<Step 1> Synthesis of 1- (3-bromophenyl) -1H-indole

Indole (80 g, 683 mmol), 3-bromoiodobenzene (290 g, 1.02 mol), Cu powder (21.7 g, 341 mmol), K ₂ CO ₃ (189 g, 1.37 mol), nitrobenzene (1000 mL) Were mixed and stirred at 190 占 폚 for 12 hours. After the reaction was terminated, the nitrobenzene was removed, extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 9: 1 (v / v)) to obtain 1- (3-bromophenyl) -1H-indole (103.7 g, yield 56%).

^{1 H-NMR: δ 6.67 (} d, 1H), 7.24 (m, 4H), 7.25 (d, 1H), 7.43 (d, 1H), 7.50 (d, 1H), 7.63 (m, 2H)

<Step 2> Synthesis of 1-bromo-5H-dibenzo [b, f] azepine

1000 g of PPA was added to 1- (3-bromophenyl) -1H-indole (103.7 g, 381 mmol) under nitrogen flow, and the mixture was stirred for 12 hours. After the reaction was completed, the reaction solution was poured into cold water, stirred and neutralized with aqueous NaOH solution. Then, the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the resulting organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain 1-bromo-5H-dibenzo [b, f] azepine (35.2 g, yield 34% .

^{1 H-NMR: δ 4.17 (} brs, 1H), 6.76 (t, 1H), 6.83 (t, 1H), 6.98 (s, 2H), 7.25 (m, 4H), 8.04 (d, 1H)

Synthesis of 1- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine

(35.2 g, 130 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-dibenzo [b, dioxane (36.1 g, 142 mmol), Pd (dppf) Cl ₂ (11.3 g, 13.0 mmol), KOAc (36.5 g, 388 mmol) and 1,4- ) Were mixed and stirred at 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 1- (4,4,5,5- -1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine (25.6 g, yield 62%).

^{1 H-NMR: δ 1.25 (} s, 12H), 4.23 (brs, 1H), 6.75 (t, 1H), 6.83 (t, 1H), 6.98 (s, 2H), 7.20 (m, 4H), 8.02 ( d, 1 H)

<Step 4> Synthesis of 1- (2-nitrophenyl) -5H-dibenzo [b, f] azepine

(16.2 g, 80.2 mmol), 1- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine (25.6 g, 80.2 mmol), K 2 CO 3 (33.3 g, 241 mmol) and a mixture of _{THF / H 2 O (200 ml} / 50 ml) , and _{then, Pd (PPh 3) 4 (} 4.63 g, 3 mmol), which was stirred for 12 hours at 80 ° C. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then the residue was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 1- (2-nitrophenyl) -5H-dibenzo [b, f] azepine %).

^{1 H-NMR: δ 4.22 (} brs, 1H), 6.73 (t, 1H), 6.83 (t, 1H), 6.98 (s, 2H), 7.23 (m, 4H), 7.67 (d, 1H), 8.05 ( m, 3H), 8.10 (d, 1 H)

Step 5 Synthesis of 1- (2-nitrophenyl) -5-phenyl-5H-dibenzo [b, f] azepine

5-dibenzo [b, f] azepine (18.4 g, 58.6 mmol), iodobenzene (7.21 mL, 64.4 mmol), Cu powder (1.86 g, 29.3 mmol), K ₂ CO ₃ (16.2 g, 117 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C for 12 hours. After the reaction was completed, nitrobenzene was removed, and the residue was extracted with methylene chloride, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 1- (2-nitrophenyl) -5-phenyl-5H-dibenzo [b, f] azepine g, yield 65%).

¹ H-NMR:? 6.69-6.81 (m, 6H), 6.97 (s, 2H), 7.15-7. 20 (m,

<Step 6> Synthesis of IIC-4

5-dibenzo [b, f] azepine (14.9 g, 38.1 mmol), triphenylphosphine (25.0 g, 95.4 mmol), 1,2-dichlorobenzene (150 mL) And the mixture was stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain compound IIC-4 (4.78 g, yield 35%).

¹ H-NMR:? 6.68-6.76 (m, 5H), 6.99 (m, 3H), 7.20-7.25 (m, 4H), 7.35-7.40 , 1H)

[Preparation Example 4] Synthesis of IIC-5 & IIC-6

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

(80 g, 683 mmol), 4-bromoiodobenzene (290 g, 1.02 mol), Cu powder (21.7 g, 341 mmol), K ₂ CO ₃ (189 g, 1.37 mol), nitrobenzene (1000 mL) Were mixed and stirred at 190 占 폚 for 12 hours. After the reaction was completed, nitrobenzene was removed, and the residue was extracted with methylene chloride, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 9: 1 (v / v)) to obtain 1- (4-bromophenyl) -1H-indole (103.7 g, yield 56%).

^{1 H-NMR: δ 6.54 (} d, 1H), 7.01 (t, 1H), 7.28 (d, 1H), 7.33 (t, 1H), 7.50 (d, 2H), 7.62 (d, 2H), 7.93 ( m, 2H)

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

1000 g of PPA was added to 1- (4-bromophenyl) -1H-indole (103.7 g, 381 mmol) under a nitrogen stream, followed by stirring for 12 hours. After the reaction was completed, the reaction solution was poured into cold water, stirred and neutralized with aqueous NaOH solution. Then, the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain 2-bromo-5H-dibenzo [b, f] azepine (35.2 g, yield 34% .

^{1 H-NMR: δ 4.16 (} brs, 1H), 6.73 (t, 1H), 6.82 (t, 1H), 6.97 (s, 2H), 7.23 (m, 4H), 8.01 (d, 1H)

Synthesis of 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine

(35.2 g, 130 mmol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-dibenzo [b, f] azepine dioxane (36.1 g, 142 mmol), Pd (dppf) Cl ₂ (11.3 g, 13.0 mmol), KOAc (36.5 g, 388 mmol) and 1,4- ) Were mixed and stirred at 130 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine (25.6 g, yield 62%).

^{1 H-NMR: δ 1.20 (} s, 12H), 4.18 (brs, 1H), 6.73 (t, 1H), 6.81 (t, 1H), 6.98 (s, 2H), 7.20 (m, 4H), 8.00 ( d, 1 H)

<Step 4> Synthesis of 2- (2-nitrophenyl) -5H-dibenzo [b, f] azepine

(16.2 g, 80.2 mmol), 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-dibenzo [b, f] azepine (25.6 g, 80.2 mmol), K 2 CO 3 (33.3 g, 241 mmol) and a mixture of _{THF / H 2 O (200 ml} / 50 ml) , and _{then, Pd (PPh 3) 4 (} 4.63 g, 3 mmol), which was stirred for 12 hours at 80 ° C. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then the residue was purified by column chromatography (hexane: EA = 20: 1 (v / v)) to obtain 2- (2-nitrophenyl) -5H- dibenzo [b, f] azepine %).

^{1 H-NMR: δ 4.20 (} brs, 1H), 6.80 (t, 1H), 6.86 (t, 1H), 6.98 (s, 2H), 7.25 (m, 4H), 7.66 (d, 1H), 8.02 ( m, 3 H), 8.18 (d, 1 H)

Step 5 Synthesis of 2- (2-nitrophenyl) -5-phenyl-5H-dibenzo [b, f] azepine

5-dibenzo [b, f] azepine (18.4 g, 58.6 mmol), iodobenzene (7.21 mL, 64.4 mmol), Cu powder (1.86 g, 29.3 mmol), K ₂ CO ₃ (16.2 g, 117 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C for 12 hours. After the reaction was terminated, the nitrobenzene was removed, extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (hexane: EA = 20: 1 (v / v)) to obtain 2- (2-nitrophenyl) -5-phenyl-5H-dibenzo [b, f] azepine g, yield 65%).

^{1 H-NMR: δ 6.65-6.80 (} m, 6H), 6.96 (s, 2H), 7.11-7.17 (m, 6H), 7.66 (t, 1H), 7.98 (m, 3H)

<Step 6> Synthesis of IIC-5 & IIC-6

Dibenzo [b, f] azepine (14.9 g, 38.1 mmol), triphenylphosphine (25.0 g, 95.4 mmol), 1,2-dichlorobenzene (150 mL) under a nitrogen atmosphere, And the mixture was stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain 4.78 g of compound IIC-5 (4.78 g, yield 35% 35%).

Of ^{IIC-5 1 H-NMR:} δ 6.63-6.70 (m, 5H), 6.97 (m, 3H), 7.14-7.23 (m, 3H), 7.34-7.38 (m, 4H), 8.04 (d, 1H) , 8.09 (d, 1 H), 8.52 (brs, 1 H)

Of ^{IIC-6 1 H-NMR:} δ 6.67-6.71 (m, 5H), 6.96 (m, 3H), 7.12-7.16 (m, 3H), 7.35-7.40 (m, 4H), 7.99 (s, 1H) , 8.11 (d, 1 H), 8.53 (brs, 1 H)

[Preparation Example 5] Synthesis of IIC-7 & IIC-8

<Step 1> Synthesis of 2- (dibenzo [b, f] thiepin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(50 g, 173 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1 Dioxaborolane (48.3 g, 190 mmol), Pd (dppf) Cl ₂ (14.1 g, 17.3 mmol), KOAc (50.9 g, 519 mmol) and 1,4-dioxane And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (dibenzo [b, f] thiepin-2 -yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (36.0 g, yield 62%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.99 (s, 2H), 7.10 (t, 1H), 7.18 (t, 1H), 7.30 (d, 1H), 7.40 (m, 4H)

<Step 2> Synthesis of 2- (2-nitrophenyl) dibenzo [b, f] thiepine

(21.6 g, 107 mmol), 2- (dibenzo [b, f] thiepin-2-yl) -4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (36.0 g, 107 mmol), K ₂ CO ₃ (44.4 g, 321 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed and Pd (PPh ₃ ) ₄ (6.18 g, And the mixture was stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 2- (2-nitrophenyl) dibenzo [b, f] thiepine (25.9 g, yield 73% .

¹ H-NMR:? 6.99 (s, 2H), 7.10 (t, IH), 7.18 (t, IH), 7.30 (d, IH), 7.42-7.47 7.86 (m, 2 H), 8.02 (m, 2 H)

<Step 3> Synthesis of IIC-7 & IIC-8

(25.9 g, 78.3 mmol), triphenylphosphine (51.2 g, 195 mmol) and 1,2-dichlorobenzene (250 ml) were added under a nitrogen atmosphere and stirred for 12 hours. Respectively. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the resulting organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain 8.20 g of compound IIC-7 (yield: 35% 35%).

Of ^{IIC-7 1 H-NMR:} δ 6.97 (m, 3H), 7.10 (t, 1H), 7.18 (t, 1H), 7.30 (m, 2H), 7.42 (d, 1H), 7.50 (t, 1H ), 7.63 (d, IH), 7.77 (d, IH), 8.08

¹ of the IIC-8 H-NMR: δ 6.98 (s, 2H), 7.10 (t, 1H), 7.18 (t, 1H), 7.28 (m, 2H), 7.34 (s, 1H), 7.40 (d, 1H ), 7.50 (t, IH), 7.63 (d, IH), 8.04

[Preparation Example 6] Synthesis of IIC-9 & IIC-10

<Step 1> Synthesis of 2- (dibenzo [b, f] thiepin-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(50 g, 173 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1 Dioxaborolane (48.3 g, 190 mmol), Pd (dppf) Cl ₂ (14.1 g, 17.3 mmol), KOAc (50.9 g, 519 mmol) and 1,4-dioxane And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (dibenzo [b, f] thiepin-3 -yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (36.0 g, yield 62%).

¹ H-NMR:? 1.24 (s, 12H), 6.99 (s, 2H), 7.10 (t, d, 1 H)

<Step 2> Synthesis of 3- (2-nitrophenyl) dibenzo [b, f] thiepine

(21.6 g, 107 mmol), 2- (dibenzo [b, f] thiepin-3-yl) -4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (36.0 g, 107 mmol) , K 2 CO 3 (44.4 g, 321 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , and _{then, Pd (PPh 3) 4 (} 6.18 g, 5 mmol ) And the mixture was stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 3- (2-nitrophenyl) dibenzo [b, f] thiepine (25.9 g, yield 73% .

^{1 H-NMR: δ 6.99 (} s, 2H), 7.10 (t, 1H), 7.18 (t, 1H), 7.36 (m, 3H), 7.41 (m, 2H), 7.67 (t, 1H), 7.89 ( t, 1 H), 8.03 (m, 2 H)

<Step 3> Synthesis of IIC-9 & IIC-10

(25.9 g, 78.3 mmol), triphenylphosphine (51.2 g, 195 mmol) and 1,2-dichlorobenzene (250 ml) were added thereto under nitrogen atmosphere and stirred for 12 hours. Respectively. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . Compound IIC-9 (8.20 g, yield 35%) and compound IIC-10 (8.20 g, yield 35%) were purified by column chromatography (Hexane: MC = 2: 1 (v / v) Yield: 35%).

Of ^{IIC-9 1 H-NMR:} δ 6.98 (s, 2H), 7.10 (t, 1H), 7.18 (t, 1H), 7.28 (m, 2H), 7.42 (m, 2H), 7.50 (t, 1H ), 7.63 (d, IH), 8.07 (d, IH), 8.12

Of ^{IIC-10 1 H-NMR:} δ 6.99 (s, 2H), 7.10 (t, 1H), 7.18 (t, 1H), 7.34 (m, 3H), 7.38 (s, 1H), 7.53 (t, 1H ), 7.63 (d, IH), 8.09 (s, IH), 8.12

[Preparation Example 7] Synthesis of IIC-11

<Step 1> Synthesis of 2- (dibenzo [b, f] thiepin-4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(50 g, 173 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1 Dioxaborolane (48.3 g, 190 mmol), Pd (dppf) Cl ₂ (14.1 g, 17.3 mmol), KOAc (50.9 g, 519 mmol) and 1,4-dioxane And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (dibenzo [b, f] thiepin-4 -yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (36.0 g, yield 62%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.99 (s, 2H), 7.10 (t, 1H), 7.18 (m, 2H), 7.34 (m, 2H), 7.41 (m, 2H)

<Step 2> Synthesis of 4- (2-nitrophenyl) dibenzo [b, f] thiepine

(21.6 g, 107 mmol), 2- (dibenzo [b, f] thiepin-4-yl) -4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (36.0 g, 107 mmol) , K 2 CO 3 (44.4 g, 321 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , and _{then, Pd (PPh 3) 4 (} 6.18 g, 5 mmol ) And the mixture was stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 4- (2-nitrophenyl) dibenzo [b, f] thiepine (25.9 g, yield 73% .

^{1 H-NMR: δ 6.99 (} s, 2H), 7.10 (t, 1H), 7.18 (t, 1H), 7.28 (m, 3H), 7.43 (m, 2H), 7.67 (t, 1H), 7.90 ( t, 1 H), 8.03 (m, 2 H)

<Step 3> Synthesis of IIC-11

(25.9 g, 78.3 mmol), triphenylphosphine (51.2 g, 195 mmol) and 1,2-dichlorobenzene (250 ml) were added thereto under a nitrogen atmosphere and stirred for 12 hours. Respectively. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain compound IIC-11 (8.20 g, yield 35%).

¹ of the IIC-11 H-NMR: δ 6.98 (s, 2H), 7.10 (t, 1H), 7.18 (t, 1H), 7.30 (m, 2H), 7.39 (m, 2H), 7.50 (m, 2H ), 7.63 (d, 1 H), 8.12 (d, 1 H), 8.51 (br s,

[Preparation Example 8] Synthesis of IIC-12

<Step 1> Synthesis of 2- (dibenzo [b, f] thiepin-1-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(50 g, 173 mmol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1 Dioxaborolane (48.3 g, 190 mmol), Pd (dppf) Cl ₂ (14.1 g, 17.3 mmol), KOAc (50.9 g, 519 mmol) and 1,4-dioxane And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (dibenzo [b, f] thiepin-1 -yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (36.0 g, yield 62%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.99 (s, 2H), 7.10 (m, 2H), 7.18 (t, 1H), 7.31 (d, 1H), 7.41 (m, 2H), 7.49 ( d, 1 H)

<Step 2> Synthesis of 1- (2-nitrophenyl) dibenzo [b, f] thiepine

(21.6 g, 107 mmol), 2- (dibenzo [b, f] thiepin-1-yl) -4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (36.0 g, 107 mmol) , K 2 CO 3 (44.4 g, 321 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , and _{then, Pd (PPh 3) 4 (} 6.18 g, 5 mmol ) And the mixture was stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 1- (2-nitrophenyl) dibenzo [b, f] thiepine (25.9 g, yield 73% .

^{1 H-NMR: δ 6.99 (} s, 2H), 7.14-7.18 (m, 3H), 7.31 (d, 1H), 7.37 (d, 1H), 7.41 (d, 1H), 7.67 (t, 1H), 7.90 (t, 1 H), 8.02-8.06 (m, 3 H)

<Step 3> Synthesis of IIC-12

(25.9 g, 78.3 mmol), triphenylphosphine (51.2 g, 195 mmol) and 1,2-dichlorobenzene (250 ml) were added thereto under nitrogen atmosphere and stirred for 12 hours. Respectively. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain compound IIC-12 (8.20 g, yield 35%).

Of ^{IIC-12 1 H-NMR:} δ 6.98 (s, 2H), 7.02 (d, 1H), 7.10 (t, 1H), 7.18 (t, 1H), 7.30 (m, 3H), 7.39 (d, 1H ), 7.50 (t, IH), 7.63 (d, IH), 8.06

[Preparation Example 9] Synthesis of IIC-13 & IIC-14

<Step 1> Synthesis of 2- (dibenzo [b, f] oxepin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(50 g, 183 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1 Dioxaborolane (51.1 g, 201 mmol), Pd (dppf) Cl ₂ (14.9 g, 18.3 mmol), KOAc (53.9 g, 549 mmol) and 1,4-dioxane And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (dibenzo [b, f] oxepin-2 -yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (36.3 g, yield 62%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.99 (s, 2H), 7.15 (m, 2H), 7.26 (t, 1H), 7.30 (d, 1H), 7.56 (m, 2H), 7.85 ( d, 1 H)

<Step 2> Synthesis of 2- (2-nitrophenyl) dibenzo [b, f] oxepine

(22.9 g, 114 mmol), 2- (dibenzo [b, f] oxepin-2-yl) -4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (36.3 g, 114 mmol) , K 2 CO 3 (47.0 g, 340 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , and _{then, Pd (PPh 3) 4 (} 6.59 g, 6 mmol ) And the mixture was stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 26.1 g of 2- (2-nitrophenyl) dibenzo [b, f] oxepine .

^{1 H-NMR: δ 6.99 (} s, 2H), 7.19 (m, 2H), 7.26 (t, 1H), 7.32 (d, 1H), 7.64 (m, 2H), 7.88 (m, 2H), 8.04 ( m, 3H)

<Step 3> Synthesis of IIC-13 & IIC-14

Dibenzo [b, f] oxepine (26.1 g, 82.9 mmol), triphenylphosphine (54.4 g, 207 mmol) and 1,2-dichlorobenzene (250 ml) were added thereto under a nitrogen stream. Respectively. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain Compound IIC-13 (8.22 g, yield 35%) and Compound IIC- 35%).

¹ H-NMR of the IIC-13: δ 6.98 (s , 2H), 7.18 (t, 1H), 7.30 (m, 4H), 7.50 (t, 1H), 7.63 (d, 1H), 7.85 (d, 1H ), 8.03 (d, IH), 8.09 (d, IH), 8.50 (brs, IH)

¹ H-NMR of the IIC-14: δ 6.99 (s , 2H), 7.06 (s, 1H), 7.18 (t, 1H), 7.30 (m, 3H), 7.50 (t, 1H), 7.63 (d, 1H ), 7.85 (d, IH), 8.10 (s, IH), 8.12

[Preparation Example 10] Synthesis of IIC-15 & IIC-16

<Step 1> Synthesis of 2- (dibenzo [b, f] oxepin-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A solution of 3-bromodibenzo [b, f] oxepine (50 g, 183 mmol), 4,4,4 ', 4,5,5,5,5-octamethyl- 2,2'- Dioxaborolane (51.1 g, 201 mmol), Pd (dppf) Cl ₂ (14.9 g, 18.3 mmol), KOAc (53.9 g, 549 mmol) and 1,4-dioxane And the mixture was stirred at 130 DEG C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (dibenzo [b, f] oxepin- -yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (36.3 g, yield 62%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.99 (s, 2H), 7.10 (s, 1H), 7.17 (t, 1H), 7.28 (m, 2H), 7.47 (m, 2H), 7.85 ( d, 1 H)

<Step 2> Synthesis of 3- (2-nitrophenyl) dibenzo [b, f] oxepine

(22.9 g, 114 mmol), 2- (dibenzo [b, f] oxepin-3-yl) -4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (36.3 g, 114 mmol) , K 2 CO 3 (47.0 g, 340 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , and _{then, Pd (PPh 3) 4 (} 6.59 g, 6 mmol ) And the mixture was stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 3- (2-nitrophenyl) dibenzo [b, f] oxepine (26.1 g, yield 73% .

^{1 H-NMR: δ 6.99 (} s, 2H), 7.17 (t, 1H), 7.30 (m, 3H), 7.52 (m, 2H), 7.67 (t, 1H), 7.88 (m, 2H), 8.02 ( m, 2H)

<Step 3> Synthesis of IIC-15 & IIC-16

Dibenzo [b, f] oxepine (26.1 g, 82.9 mmol), triphenylphosphine (54.4 g, 207 mmol) and 1,2-dichlorobenzene (250 ml) were added thereto under a nitrogen stream. Respectively. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain Compound IIC-15 (8.22 g, yield 35%) and Compound IIC- 35%).

Of ^{IIC-15 1 H-NMR:} δ 6.98 (s, 2H), 7.18 (t, 1H), 7.30 (m, 3H), 7.50 (t, 1H), 7.60 (m, 2H), 7.85 (d, 1H ), 8.03 (d, IH), 8.09 (d, IH), 8.50 (brs, IH)

Of ^{IIC-16 1 H-NMR:} δ 6.99 (s, 2H), 7.18 (t, 1H), 7.28 (m, 3H), 7.50 (m, 2H), 7.63 (d, 1H), 7.85 (d, 1H ), 8.09 (s, IH), 8.12 (d, IH), 8.51 (brs, IH)

[Preparation Example 11] Synthesis of IIC-17

<Step 1> Synthesis of 2- (dibenzo [b, f] oxepin-4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A solution of 4-bromodibenzo [b, f] oxepine (50 g, 183 mmol), 4,4,4 ', 4,5,5,5,5-octamethyl-2,2'- Dioxaborolane (51.1 g, 201 mmol), Pd (dppf) Cl ₂ (14.9 g, 18.3 mmol), KOAc (53.9 g, 549 mmol) and 1,4-dioxane And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (dibenzo [b, f] oxepin- -yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (36.3 g, yield 62%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.99 (s, 2H), 7.17 (m, 2H), 7.29 (m, 2H), 7.56 (d, 1H), 7.85 (m, 2H)

<Step 2> Synthesis of 4- (2-nitrophenyl) dibenzo [b, f] oxepine

(22.9 g, 114 mmol), 2- (dibenzo [b, f] oxepin-4-yl) -4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (36.3 g, 114 mmol) , K 2 CO 3 (47.0 g, 340 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , and _{then, Pd (PPh 3) 4 (} 6.59 g, 6 mmol ) And the mixture was stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 4- (2-nitrophenyl) dibenzo [b, f] oxepine (26.1 g, yield 73% .

^{1 H-NMR: δ 6.99 (} s, 2H), 7.23 (m, 3H), 7.32 (d, 1H), 7.63 (m, 2H), 7.86 (m, 3H), 8.02 (m, 2H)

<Step 3> Synthesis of IIC-17

(26.1 g, 82.9 mmol), triphenylphosphine (54.4 g, 207 mmol) and 1,2-dichlorobenzene (250 ml) were placed under a nitrogen atmosphere and stirred for 12 hours. Respectively. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain compound IIC-17 (8.22 g, yield 35%).

Of ^{IIC-17 1 H-NMR:} δ 6.99 (s, 2H), 7.18 (t, 1H), 7.26-7.34 (m, 4H), 7.50 (d, 1H), 7.65 (m, 2H), 7.85 (d , 8.11 (d, 1 H), 8.51 (brs, 1 H)

[Preparation Example 12] Synthesis of IIC-18

<Step 1> Synthesis of 2- (dibenzo [b, f] oxepin-1-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(50 g, 183 mmol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1 Dioxaborolane (51.1 g, 201 mmol), Pd (dppf) Cl ₂ (14.9 g, 18.3 mmol), KOAc (53.9 g, 549 mmol) and 1,4-dioxane And the mixture was stirred at 130 DEG C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and then dried over MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (dibenzo [b, f] oxepin-1 -yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (36.3 g, yield 62%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.99 (s, 2H), 7.17 (t, 1H), 7.27 (m, 2H), 7.32 (m, 2H), 7.47 (d, 1H), 7.85 ( d, 1 H)

<Step 2> Synthesis of 1- (2-nitrophenyl) dibenzo [b, f] oxepine

(22.9 g, 114 mmol), 2- (dibenzo [b, f] oxepin-1-yl) -4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (36.3 g, 114 mmol) , K 2 CO 3 (47.0 g, 340 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , and _{then, Pd (PPh 3) 4 (} 6.59 g, 6 mmol ) And the mixture was stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 1- (2-nitrophenyl) dibenzo [b, f] oxepine (26.1 g, yield 73% .

^{1 H-NMR: δ 6.99 (} s, 2H), 7.17 (t, 1H), 7.30 (m, 4H), 7.67 (t, 1H), 7.88 (m, 2H), 8.03 (m, 3H)

<Step 3> Synthesis of IIC-18

(26.1 g, 82.9 mmol), triphenylphosphine (54.4 g, 207 mmol) and 1,2-dichlorobenzene (250 ml) were placed under a nitrogen atmosphere and stirred for 12 hours. Respectively. After the reaction was completed, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, followed by addition of MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain compound IIC-18 (8.22 g, yield 35%).

Of ^{IIC-18 1 H-NMR:} δ 6.99 (s, 2H), 7.16 (t, 1H), 7.26-7.32 (m, 4H), 7.44 (d, 1H), 7.50 (t, 1H), 7.63 (d , 7.85 (d, IH), 8.11 (d, IH), 8.51 (brs, IH)

[Preparation Example 13] Synthesis of PCB-1

2-bromo-9-phenyl-9H-carbazole (174.0 g, 540.0 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi Dioxaborolane (150.8 g, 594.0 mmol), Pd (dppf) Cl ₂ (62.4 g, 54.0 mmol), KOAc (152.5 g, 1.62 mol) and 1,4- And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain 169.5 g (yield: 85% &Lt; / RTI &gt;

^{1 H-NMR: δ 1.24 (} s, 12H), 7.25-7.33 (m, 2H), 7.43-7.58 (m, 6H), 7.83 (s, 1H), 7.94 (d, 1H), 8.12 (d, 1H ), 8.55 (d, 1 H)

[Preparation Example 14] Synthesis of PCB-2

(174.0 g, 540.0 mmol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi Dioxaborolane (150.8 g, 594.0 mmol), Pd (dppf) Cl ₂ (62.4 g, 54.0 mmol), KOAc (152.5 g, 1.62 mol) and 1,4- And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain 161.5 g of compound PCB- .

^{1 H-NMR: δ 1.24 (} s, 12H), 7.25-7.33 (m, 2H), 7.45-7.63 (m, 7H), 7.94-7.98 (m, 2H), 8.55 (d, 1H)

[Preparation Example 15] Synthesis of AzC-1

<Step 1> Synthesis of 2- (1H-indol-5-yl) -9-phenyl-9H-carbazole

5-bromo-1H-indole ( 100 g, 439.2 mmol), PCB-1 (194.6 g, 527.0 mmol), Pd (PPh 3) 4 (25.4 g, 22.0 mmol), K 2 CO 3 (121.4 g in a nitrogen atmosphere , 878 mmol) and 1,4-dioxane / H ₂ O (200 ml / 50 ml) were mixed and stirred at 120 ° C for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain 118.1 g of 2- (1H-indol- Yield: 75%).

¹ H-NMR:? 6.45 (d, 1H), 7.27-7.29 (m, 2H), 7.45-7.77 (m, 10H), 7.87 , 1 H), 10.1 (b, 1 H)

Synthesis of 2- (1- (9,9-dimethyl-9H-fluoren-3-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole

3-bromo-9,9-dimethyl-9H-fluorene (108.0 g, 395.3 mmol) was added to a solution of 2- (1H-indol-5-yl) -9- , Cu (10.5 g, 164.7 mmol), K ₂ CO ₃ (91.1 g, 658.8 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 6: 1 (v / v) 9H-fluoren-3-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole (146.9 g, yield 81%).

^{1 H-NMR: δ 1.72 (} s, 6H), 6.52 (d, 1H), 7.06-7.07 (m, 2H), 7.17-7.34 (m, 5H), 7.45-7.60 (m, 8H), 7.77-7.79 (m, 2H), 7.87-8.00 (m, 3H), 8.16-8.18 (m, 2H), 8.55

<Step 3> Synthesis of AzC-1

9H-fluoren-3-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole (146.9 g, 266.8 mmol), polyphosphoric acid (734.6 g) were mixed and stirred at 100 ° C for 12 hours. After completion of the reaction, the reaction product was extracted from water and then filtered to obtain a compound AzC-1 (45.5 g, yield: 31%).

^{1 H-NMR: δ 1.72 (} s, 6H), 6.69 (d, 1H), 6.99-7.04 (m, 3H), 7.28-7.63 (m, 14H), 7.82-7.87 (m, 2H), 8.10-8.12 (m, 2H), 8.42 (b, IH), 8.49 (d, IH)

[Preparation Example 16] Synthesis of AzC-2

Synthesis of 2- (1- (dibenzo [b, d] furan-2-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole

2-bromodibenzo [b, d] furan (124.1 g, 502.2 mmol), Cu (13.3 g, g, 209.2 mmol), K ₂ CO ₃ (115.7 g, 837.0 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and then dried over MgSO ₄ and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 2- (1- (dibenzo [ furan-2-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole (171.2 g, yield 78%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.25-7.66 (m, 14H), 7.77-7.80 (m, 3H), 7.89-8.00 (m, 3H), 8.16-8.18 (m, 2H), 8.55 (d, 1 H)

<Step 2> Synthesis of AzC-2

5-yl) -9-phenyl-9H-carbazole (171.2 g, 326.4 mmol), polyphosphoric acid (856.2 g) were mixed and stirred at 100 占 폚 for 12 hours. After the reaction was completed, the reaction product was extracted from water and then filtered to obtain AzC-2 (47.9 g, yield: 28%).

^{1 H-NMR: δ 6.69 (} d, 1H), 6.99-7.01 (m, 2H), 7.29-7.66 (m, 15H), 7.82 (s, 1H), 7.89 (d, 1H), 8.10-8.12 (m , 2H), 8.42 (b, IH), 8.49 (d, IH)

[Preparation Example 17] Synthesis of AzC-3

Synthesis of 2- (1- (dibenzo [b, d] thiophen-2-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole

2-bromodibenzo [b, d] thiophene (132.2 g, 502.2 mmol), Cu (13.3 g, g, 209.2 mmol), K ₂ CO ₃ (115.7 g, 837.0 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and then dried over MgSO ₄ and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 2- (1- (dibenzo [ 2-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole (169.7 g, yield 75%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.25-7.33 (m, 2H), 7.45-7.62 (m, 10H), 7.77-7.79 (m, 2H), 7.94-8.00 (m, 5H), 8.16 -8.18 (m, 2H), 8.45 (d, IH), 8.55 (d, IH)

<Step 2> Synthesis of AzC-3

9-phenyl-9H-carbazole (169.7 g, 418.5 mmol), polyphosphoric acid (848.5 g, g) were mixed and stirred at 100 占 폚 for 12 hours. After completion of the reaction, the reaction mixture was extracted with water and then filtered to obtain Compound AzC-3 (56.0 g, yield 33%).

^{1 H-NMR: δ 6.69 (} d, 1H), 6.99-7.01 (m, 2H), 7.29 (dd, 1H), 7.39-7.63 (m, 12H), 7.77-7.82 (m, 2H), 7.98 (d , 1H), 8.10-8.12 (m, 2H), 8.42-8. 49 (m, 3H)

[Preparation Example 18] Synthesis of AzC-4

<Step 1> Synthesis of 3- (1H-indol-5-yl) -9-phenyl-9H-carbazole

5-bromo-1H-indole ( 100 g, 439.2 mmol), PCB-2 (194.6 g, 527.0 mmol), Pd (PPh 3) 4 (25.4 g, 22.0 mmol), K 2 CO 3 (121.4 g in a nitrogen atmosphere , 878 mmol) and 1,4-dioxane / H ₂ O (200 ml / 50 ml) were mixed and stirred at 120 ° C for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain 127.5 g of 3- (1H-indol- Yield: 81%).

¹ H-NMR:? 6.45 (d, 1H), 7.27-7.29 (m, 2H), 7.45-7.77 (m, 10H), 7.87 , 2H), 10.1 (b, 1 H)

Synthesis of 3- (1- (9,9-dimethyl-9H-fluoren-3-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole

3-bromo-9,9-dimethyl-9H-fluorene (116.6 g, 426.9 mmol) was added to a solution of 3- (1H-indol-5-yl) -9- , Cu (11.3 g, 177.9 mmol), K ₂ CO ₃ (98.3 g, 711.5 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 6: 1 (v / v) 9H-fluoren-3-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole (156.7 g, yield 80%).

^{1 H-NMR: δ 1.72 (} s, 6H), 6.52 (d, 1H), 7.06-7.07 (m, 2H), 7.17-7.34 (m, 5H), 7.45-7.69 (m, 8H), 7.77-7.79 (m, 2H), 7.87-8.00 (m, 4H), 8.18 (d,

<Step 3> Synthesis of AzC-4

9H-fluoren-3-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole (156.7 g, 284.6 mmol), polyphosphoric acid (783.6 g) were mixed and stirred at 100 ° C for 12 hours. After completion of the reaction, the reaction product was extracted with water and then filtered to obtain AzC-4 (51.7 g, yield 33%).

^{1 H-NMR: δ 1.72 (} s, 6H), 6.69 (d, 1H), 6.99-7.04 (m, 3H), 7.28-7.63 (m, 13H), 7.77 (s, 1H), 7.82-7.87 (m , 2H), 8.00-8.12 (m, 3H), 8.42 (b, IH)

[Preparation Example 19] Synthesis of AzC-5

Synthesis of 3- (1- (dibenzo [b, d] furan-2-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole

B, d] furan (124.1 g, 502.2 mmol), Cu (13.3 g, 418.5 mmol), 2- g, 209.2 mmol), K ₂ CO ₃ (115.7 g, 837.0 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 3- (1- (dibenzo [ furan-2-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole (160.1 g, yield 73%).

¹ H-NMR:? 6.52 (d, 1H), 7.25-8.00 (m, 21H), 8.18

<Step 2> Synthesis of AzC-5

9-phenyl-9H-carbazole (160.1 g, 305.5 mmol), polyphosphoric acid (800.7 g, g) were mixed and stirred at 100 占 폚 for 12 hours. After completion of the reaction, the reaction product was extracted from water and then filtered to obtain a compound AzC-5 (48.0 g, yield 30%).

^{1 H-NMR: δ 6.69 (} d, 1H), 6.99-7.01 (m, 2H), 7.29-7.66 (m, 14H), 7.77-7.89 (m, 3H), 8.00 (d, 1H), 8.10-8.12 (m, 2 H), 8.42 (b, 1 H)

[Preparation Example 20] Synthesis of AzC-6

Synthesis of 3- (1- (dibenzo [b, d] thiophen-2-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole

B, d] thiophene (132.2 g, 502.2 mmol), Cu (13.3 g, 418.5 mmol), 2- g, 209.2 mmol), K ₂ CO ₃ (115.7 g, 837.0 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 3- (1- (dibenzo [ 2-yl) -1H-indol-5-yl) -9-phenyl-9H-carbazole (172.0 g, yield 76%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.25-7.33 (m, 2H), 7.45-7.58 (m, 9H), 7.69 (d, 1H), 7.77-7.79 (m, 2H), 7.87-8.00 (m, 6H), 8.18 (d, IH), 8.45 (d, IH), 8.55

<Step 2> Synthesis of AzC-6

9-phenyl-9H-carbazole (172.0 g, 318.0 mmol), polyphosphoric acid (859.8 mmol) was added to a solution of 3- (1- g) were mixed and stirred at 100 占 폚 for 12 hours. After completion of the reaction, the reaction mixture was extracted from water and then filtered to obtain Compound AzC-6 (43.0 g, yield 25%).

^{1 H-NMR: δ 6.69 (} d, 1H), 6.99-7.01 (m, 2H), 7.29 (dd, 1H), 7.39-7.63 (m, 11H), 7.77-7.82 (m, 3H), 7.98-8.00 (m, 2H), 8.12-8.18 (m, 2H), 8.42 (b, 1H), 8.45

[Preparation Example 21] Synthesis of AzC-7

<Step 1> Synthesis of 2- (1H-indol-5-yl) -9-phenyl-9H-carbazole

5-bromo-1H-indole ( 100 g, 439.2 mmol), PCB-1 (194.6 g, 527.0 mmol), Pd (PPh 3) 4 (25.4 g, 22.0 mmol), K 2 CO 3 (121.4 g in a nitrogen atmosphere , 878 mmol) and 1,4-dioxane / H ₂ O (200 ml / 50 ml) were mixed and stirred at 120 ° C for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then the residue was purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to obtain 132.2 g of 2- (1H- Yield: 84%).

¹ H-NMR:? 6.45 (d, 1H), 7.25-7.33 (m, 3H), 7.45-7.94 (m, 11H), 8.18 )

Synthesis of 9-phenyl-2- (1- (9-phenyl-9H-carbazol-3-yl) -1H-indol-5-yl) -9H-carbazole

9-phenyl-9H-carbazole (142.6 g, 442.7 mmol), Cu (3-bromo-9- (11.7 g, 184.5 mmol), K ₂ CO ₃ (102.0 g, 737.8 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 8: 1 (v / v)) to obtain 9- phenyl-9H-carbazol-3-yl) -1H-indol-5-yl) -9H-carbazole (192.5 g, yield 87%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.25-7.7.33 (m, 5H), 7.45-7.63 (m, 13H), 7.77-7.79 (m, 2H), 7.94-8.00 (m, 4H) , 8.14-8.17 (m, 2H), 8.54-8.56 (m, 2H)

<Step 3> Synthesis of AzC-7

9H-carbazol-3-yl) -1H-indol-5-yl) -9H-carbazole (192.5 g, 321.0 mmol), polyphosphoric acid (962.4 g) were mixed and stirred at 100 占 폚 for 12 hours. After completion of the reaction, the reaction product was extracted from water and then filtered to obtain a compound AzC-7 (65.4 g, yield 34%).

^{1 H-NMR: δ 6.69 (} d, 1H), 6.99-7.01 (m, 2H), 7.29-7.63 (m, 19H), 7.79-7.82 (m, 2H), 7.94 (d, 1H), 8.12-8.18 (m, 2H), 8.42 (b, IH), 8.55 (d, IH)

[Preparation Example 22] Synthesis of AzC-8

<Step 1> Synthesis of 3- (1H-indol-5-yl) -9-phenyl-9H-carbazole

5-bromo-1H-indole ( 100 g, 439.2 mmol), PCB-2 (194.6 g, 527.0 mmol), Pd (PPh 3) 4 (25.4 g, 22.0 mmol), K 2 CO 3 (121.4 g in a nitrogen atmosphere , 878 mmol) and 1,4-dioxane / H ₂ O (200 ml / 50 ml) were mixed and stirred at 120 ° C for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to obtain 3- (1H- indol- Yield: 80%).

¹ H-NMR:? 6.45 (d, 1H), 7.25-7.33 (m, 3H), 7.45-7.94 (m, 12H), 8.55

<Step 2> Synthesis of 3,3 '- (1H-indole-1,5-diyl) bis (9-phenyl-9H-carbazole)

(125.8 g, 351.3 mmol), 3-bromo-9-phenyl-9H-carbazole (135.8 g, 421.6 mmol), Cu (11.2 g, 175.7 mmol), K ₂ CO ₃ (97.1 g, 702.7 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then remove the water with MgSO ₄ and purified by column chromatography (Hexane: EA = 8: 1 (v / v)) to give 3,3 '- (1H-indole- 1, 5-diyl) bis (9-phenyl-9H-carbazole) (174.9 g, yield 83%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.25-7.7.33 (m, 5H), 7.45-7.69 (m, 13H), 7.77-7.79 (m, 2H), 7.94-8.00 (m, 5H) , 8.18 (d, 1 H), 8.54 - 8.56 (m, 2 H)

<Step 3> Synthesis of AzC-8

9-phenyl-9H-carbazole (174.9 g, 291.6 mmol) and polyphosphoric acid (874.5 g) were mixed in a nitrogen stream at 100 ° C and 12 Lt; / RTI &gt; After the reaction was completed, the reaction product was extracted from water and then filtered to obtain a compound AzC-8 (52.5 g, yield 30%).

¹ H-NMR:? 6.69 (d, 1H), 6.99-7.01 (m, 2H), 7.25-7.69 (m, 19H), 7.77-7.94 , &Lt; / RTI &gt; 1H), 8.55 (d, 1H)

[Preparation Example 23] Synthesis of AzC-9

<Step 1> Synthesis of 5- (dibenzo [b, d] furan-4-yl) -1H-indole

(100 g, 439.2 mmol), 2- (dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1,3,2- dioxane / H ₂ O (200 mL / 50 mL) was added to a solution of the title compound (155.0 g, 527.0 mmol), Pd (PPh ₃ ) ₄ (25.4 g, 22.0 mmol), K ₂ CO ₃ ) Were mixed and stirred at 120 ° C for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. Dibenzo [b, d] furan-4-yl) -1H-indole (104.5 g, yielded as a colorless powder) was obtained by removing the solvent from the obtained organic layer and then purifying by column chromatography (Hexane: EA = 7: Yield: 84%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27-7.38 (m, 4H), 7.66-7.89 (m, 7H), 10.1 (b, 1H)

Synthesis of 3- (5- (dibenzo [b, d] furan-4-yl) -1H-indol-1-yl) -9-phenyl-9H-

3-bromo-9-phenyl-9H-carbazole (142.6 g, 442.7 mmol), Cu (dibenzo [b, d] furan-4-yl) -1H- indole (104.5 g, 368.9 mmol) (11.7 g, 184.5 mmol), K ₂ CO ₃ (102.0 g, 737.8 mmol) and nitrobenzene (1000 ml) were mixed and stirred at 210 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain 3- (5- (dibenzo [ furan-4-yl) -1H-indol-1-yl) -9-phenyl-9H-carbazole (145.2 g, yield 75%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.25-7.67 (m, 14H), 7.77-8.00 (m, 7H), 8.18 (d, 1H), 8.55 (b, 1H)

<Step 3> Synthesis of AzC-9

9-phenyl-9H-carbazole (145.2 g, 276.7 mmol), polyphosphoric acid (725.8 g, g) were mixed and stirred at 100 占 폚 for 12 hours. After the reaction was completed, the reaction product was extracted from water and then filtered to obtain a compound AzC-9 (47.9 g, yield 33%).

¹ H-NMR:? 6.69 (d, 1 H), 6.99-7.00 (m, 2H), 7.31-7.66 (m, 15H), 7.81-7.89 , 1H)

[Preparation Example 24] Synthesis of AzC-10

<Step 1> Synthesis of 5- (dibenzo [b, d] furan-4-yl) -1H-indole

(100 g, 439.2 mmol), 2- (dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1,3,2- dioxane / H ₂ O (200 mL / 50 mL) was added to a solution of the title compound (155.0 g, 527.0 mmol), Pd (PPh ₃ ) ₄ (25.4 g, 22.0 mmol), K ₂ CO ₃ ) Were mixed and stirred at 120 ° C for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain 5- (dibenzo [b, d] furan- Yield: 76%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27-7.38 (m, 4H), 7.66-7.89 (m, 7H), 10.1 (b, 1H)

Synthesis of dibenzo [b, d] furan-4-yl) -1- (9,9-dimethyl-9H-fluoren-3-yl)

3-bromo-9,9-dimethyl-9H-fluorene (109.4 g, 400.5 mmol) was added to a solution of 5- (dibenzo [b, d] furan- , Cu (10.6 g, 166.9 mmol), K ₂ CO ₃ (92.3 g, 667.6 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (hexane: EA = 6: 1 (v / v)) to obtain 5- (dibenzo [b, -yl) -1- (9,9-dimethyl-9H-fluoren-3-yl) -1H-indole (117.5 g, yield 74%).

^{1 H-NMR: δ 1.72 (} s, 6H), 6.52 (d, 1H), 7.06-7.07 (m, 2H), 7.17 (dd, 1H), 7.32-7.38 (m, 5H), 7.60-7.66 (m , &Lt; / RTI &gt; 3H), 7.77-7.89 (m, 5H)

<Step 3> Synthesis of AzC-10

(Dibenzo [b, d] furan-4-yl) -1- (9,9-dimethyl-9H-fluoren-3-yl) -1H- indole (117.5 g, 247.0 mmol), polyphosphoric acid (587.3 g) were mixed and stirred at 100 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted from water and then filtered to obtain Compound AzC-10 (34.1 g, yield 29%).

¹ H-NMR:? 1.72 (s, 6H), 6.69 (d, 1H), 6.99-7.04 (m, 3H), 7.28-7.38 ), 7.66 (d, 1 H), 7.81-7.89 (m, 5H), 8.42 (b,

[Preparation Example 25] Synthesis of AzC-11

Synthesis of dibenzo [b, d] furan-2-yl) -5- (dibenzo [b, d] furan-4-yl)

Dibenzo [b, d] furan-4-yl) -1H-indole (80.0 g, 282.4 mmol), 2-bromodibenzo [b, d] furan (83.7 g, 338.8 mmol), Cu g, 141.2 mmol), K ₂ CO ₃ (78.1 g, 564.7 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain 1- (dibenzo [b, -yl) -5- (dibenzo [b, d] furan-4-yl) -1H-indole (100.3 g, yield 79%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.32-7.38 (m, 5H), 7.50 (d, 1H), 7.60-7.66 (m, 4H), 7.77-7.89 (m, 6H), 8.00 (d , &Lt; / RTI &gt; 1H), 8.18 (d, 1H)

<Step 2> Synthesis of AzC-11

Dibenzo [b, d] furan-2-yl) -5- (dibenzo [b, d] furan-4-yl) -1H- indole (100.3 g, 223.1 mmol), polyphosphoric acid g) were mixed and stirred at 100 占 폚 for 12 hours. After completion of the reaction, the reaction product was extracted with water and then filtered to obtain a compound AzC-11 (31.1 g, yield: 31%).

^{1 H-NMR: δ 6.69 (} d, 1H), 6.99-7.00 (m, 2H), 7.32-7.38 (m, 7H), 7.65-7.66 (m, 3H), 7.81-7.89 (m, 5H), 8.42 (b, 1H)

[Preparation Example 26] Synthesis of AzC-12

Synthesis of dibenzo [b, d] furan-4-yl) -1- (dibenzo [b, d] thiophen-2-yl)

Dibenzo [b, d] furan-4-yl) -1H-indole (80.0 g, 282.4 mmol), 2-bromodibenzo [b, d] thiophene (89.2 g, 338.8 mmol), Cu g, 141.2 mmol), K ₂ CO ₃ (78.1 g, 564.7 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 5- (dibenzo [b, -yl) -1- (dibenzo [b, d] thiophen-2-yl) -1H-indole (97.3 g, yield 74%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.38-7.66 (m, 8H), 7.77-8.00 (m, 8H), 8.18 (d, 1H), 8.45 (d, 1H)

<Step 2> Synthesis of AzC-12

Dibenzo [b, d] furan-4-yl) -1- (dibenzo [b, d] thiophen-2-yl) -1H- indole (97.3 g, 209.0 mmol), polyphosphoric acid g) were mixed and stirred at 100 占 폚 for 12 hours. After completion of the reaction, the reaction product was extracted from water and then filtered to obtain a compound AzC-12 (35.0 g, yield 36%).

^{1 H-NMR: δ 6.69 (} d, 1H), 6.99-7.00 (m, 2H), 7.32-7.40 (m, 5H), 7.50-7.52 (m, 2H), 7.66 (d, 1H), 7.77-7.89 (m, 5H), 7.98 (d, IH), 8.42 (b, IH), 8.50

[Synthesis Example 1] Synthesis of A-1

(3.5 g, 9.76 mmol), 2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t- Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the title compound A-1 (3.7 g, 65 %).

Mass (theory: 587.71 g / mol, measurement: 587 g / mol)

[Synthesis Example 2] Synthesis of A-2

The procedure of Synthesis Example 1 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-2 , Yield: 71%).

Mass (theory: 588.70 g / mol, measurement: 588 g / mol)

[Synthesis Example 3] Synthesis of A-3

The same procedure as in Synthesis Example 1 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective Compound A-3 (4.5 g, yield 78%) was obtained.

Mass (theory: 589.69 g / mol, measurement: 589 g / mol)

[Synthesis Example 4] Synthesis of A-4

The procedure of Synthesis Example 1 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine, 4 (3.9 g, yield 60%).

Mass (theory: 664.79 g / mol, measurement: 664 g / mol)

[Synthesis Example 5] Synthesis of A-5

Was prepared in the same manner as in Synthesis Example 1, except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine To obtain the target compound A-5 (4.3 g, yield 66%).

Mass (calculated: 665.78 g / mol, measured: 665 g / mol)

[Synthesis Example 6] Synthesis of A-6

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-6 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 1.

Mass (theory: 741.88 g / mol, measured: 741 g / mol)

[Synthesis Example 7] Synthesis of A-7

(3.5 g, 9.76 mmol), 2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t- Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the title compound A-7 (3.7 g, 65 %).

Mass (theory: 587.71 g / mol, measurement: 587 g / mol)

[Synthesis Example 8] Synthesis of A-8

The same procedure as in Synthesis Example 7 was carried out except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine, , Yield: 71%).

Mass (theory: 588.70 g / mol, measurement: 588 g / mol)

[Synthesis Example 9] Synthesis of A-9

The same procedure as in Synthesis Example 7 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective Compound A-9 (4.5 g, yield 78%) was obtained.

Mass (theory: 589.69 g / mol, measurement: 589 g / mol)

[Synthesis Example 10] Synthesis of A-10

The procedure of Synthetic Example 7 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine. 10 (3.9 g, yield 60%).

Mass (theory: 664.79 g / mol, measurement: 664 g / mol)

[Synthesis Example 11] Synthesis of A-11

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the title compound A-11 (4.3 g, yield 66%).

Mass (calculated: 665.78 g / mol, measured: 665 g / mol)

[Synthesis Example 12] Synthesis of A-12

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-12 (5.3 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 7.

Mass (theory: 741.88 g / mol, measured: 741 g / mol)

[Synthesis Example 13] Synthesis of A-13

(3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t-Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-13 (3.7 g, 65 %).

Mass (theory: 587.71 g / mol, measurement: 587 g / mol)

[Synthesis Example 14] Synthesis of A-14

The same procedure as in Synthesis Example 13 was carried out except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine, , Yield: 71%).

Mass (theory: 588.70 g / mol, measurement: 588 g / mol)

[Synthesis Example 15] Synthesis of A-15

The same procedure as in Synthesis Example 13 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The target compound A-15 (4.5 g, yield 78%) was obtained.

Mass (theory: 589.69 g / mol, measurement: 589 g / mol)

[Synthesis Example 16] Synthesis of A-16

The procedure of Synthesis Example 13 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6- 16 (3.9 g, yield 60%).

Mass (theory: 664.79 g / mol, measurement: 664 g / mol)

[Synthesis Example 17] Synthesis of A-17

Was obtained in the same manner as in Synthesis Example 13 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine (4.3 g, yield 66%) of the target compound A-17 was obtained.

Mass (calculated: 665.78 g / mol, measured: 665 g / mol)

[Synthesis Example 18] Synthesis of A-18

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-18 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 13.

Mass (theory: 741.88 g / mol, measured: 741 g / mol)

[Synthesis Example 19] Synthesis of A-19

(3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t-Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-19 (3.7 g, 65 %).

Mass (theory: 587.71 g / mol, measurement: 587 g / mol)

[Synthesis Example 20] Synthesis of A-20

The procedure of Synthesis Example 19 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-20 , Yield: 71%).

Mass (theory: 588.70 g / mol, measurement: 588 g / mol)

[Synthesis Example 21] Synthesis of A-21

The same procedure as in Synthesis Example 19 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-21 (4.5 g, yield 78%) was obtained.

Mass (theory: 589.69 g / mol, measurement: 589 g / mol)

[Synthesis Example 22] Synthesis of A-22

The procedure of Synthesis Example 19 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine, 22 (3.9 g, yield 60%).

Mass (theory: 664.79 g / mol, measurement: 664 g / mol)

[Synthesis Example 23] Synthesis of A-23

The same procedure as in Synthesis Example 19 was repeated, except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine To obtain the target compound A-23 (4.3 g, yield 66%).

Mass (calculated: 665.78 g / mol, measured: 665 g / mol)

[Synthesis Example 24] Synthesis of A-24

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-24 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 19.

Mass (theory: 741.88 g / mol, measured: 741 g / mol)

[Synthesis Example 25] Synthesis of A-25

(3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t-Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-25 (3.7 g, 65 %).

Mass (theory: 587.71 g / mol, measurement: 587 g / mol)

[Synthesis Example 26] Synthesis of A-26

The procedure of Synthesis Example 25 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-26 , Yield: 71%).

Mass (theory: 588.70 g / mol, measurement: 588 g / mol)

[Synthesis Example 27] Synthesis of A-27

The same procedure as in Synthesis Example 25 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-27 (4.5 g, yield 78%) was obtained.

Mass (theory: 589.69 g / mol, measurement: 589 g / mol)

[Synthesis Example 28] Synthesis of A-28

The procedure of Synthesis Example 25 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6- 28 (3.9 g, yield 60%).

Mass (theory: 664.79 g / mol, measurement: 664 g / mol)

[Synthesis Example 29] Synthesis of A-29

Was obtained in the same manner as in Synthesis Example 25 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine To obtain the target compound A-29 (4.3 g, yield 66%).

Mass (calculated: 665.78 g / mol, measured: 665 g / mol)

[Synthesis Example 30] Synthesis of A-30

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-30 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 25.

Mass (theory: 741.88 g / mol, measured: 741 g / mol)

[Synthesis Example 31] Synthesis of A-31

(3.5 g, 9.76 mmol), 2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-31 (3.7 g, 65 %).

Mass (theory: 587.71 g / mol, measurement: 587 g / mol)

[Synthesis Example 32] Synthesis of A-32

The procedure of Synthesis Example 31 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-32 , Yield: 71%).

Mass (theory: 588.70 g / mol, measurement: 588 g / mol)

[Synthesis Example 33] Synthesis of A-33

The same procedure as in Synthesis Example 31 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine To obtain the title compound A-33 (4.5 g, yield 78%).

Mass (theory: 589.69 g / mol, measurement: 589 g / mol)

[Synthesis Example 34] Synthesis of A-34

The procedure of Synthesis Example 31 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine, 34 (3.9 g, yield 60%).

Mass (theory: 664.79 g / mol, measurement: 664 g / mol)

[Synthesis Example 35] Synthesis of A-35

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the target compound A-35 (4.3 g, yield 66%).

Mass (calculated: 665.78 g / mol, measured: 665 g / mol)

[Synthesis Example 36] Synthesis of A-36

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-36 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 31.

Mass (theory: 741.88 g / mol, measured: 741 g / mol)

[Synthesis Example 37] Synthesis of A-37

(3.5 g, 9.76 mmol), 2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-37 (3.7 g, 65 %).

Mass (theory: 528.66 g / mol, measurement: 528 g / mol)

[Synthesis Example 38] Synthesis of A-38

The procedure of Synthesis Example 37 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-38 , Yield: 71%).

Mass (theory: 529.65 g / mol, measurement: 529 g / mol)

[Synthesis Example 39] Synthesis of A-39

The same procedure as in Synthesis Example 37 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-39 (4.5 g, yield 78%) was obtained.

Mass (theory: 530.64 g / mol, measured: 530 g / mol)

[Synthesis Example 40] Synthesis of A-40

The procedure of Synthesis Example 37 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine, 40 (3.9 g, yield 60%).

Mass (theory: 605.75 g / mol, measurement: 605 g / mol)

[Synthesis Example 41] Synthesis of A-41

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine To obtain the target compound A-41 (4.3 g, yield 66%).

Mass (theory: 606.74 g / mol, measurement: 665 g / mol)

[Synthesis Example 42] Synthesis of A-42

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-42 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 37.

Mass (theory: 682.83 g / mol, measured: 682 g / mol)

[Synthesis Example 43] Synthesis of A-43

(3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t-Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-43 (3.7 g, 65 %).

Mass (theory: 528.66 g / mol, measurement: 528 g / mol)

[Synthesis Example 44] Synthesis of A-44

The same procedure as in Synthesis Example 43 was carried out except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the target compound A-44 , Yield: 71%).

Mass (theory: 529.65 g / mol, measurement: 529 g / mol)

[Synthesis Example 45] Synthesis of A-45

The same procedure as in Synthesis Example 43 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-45 (4.5 g, yield 78%) was obtained.

Mass (theory: 530.64 g / mol, measured: 530 g / mol)

[Synthesis Example 46] Synthesis of A-46

The procedure of Synthesis Example 43 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine, 46 (3.9 g, yield 60%).

Mass (theory: 605.75 g / mol, measurement: 605 g / mol)

[Synthesis Example 47] Synthesis of A-47

Except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the target compound A-47 (4.3 g, yield 66%).

Mass (theory: 606.74 g / mol, measurement: 665 g / mol)

[Synthesis Example 48] Synthesis of A-48

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-48 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 43.

Mass (theory: 682.83 g / mol, measured: 682 g / mol)

[Synthesis Example 49] Synthesis of A-49

(3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t-Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-49 (3.7 g, 65 %).

Mass (theory: 528.66 g / mol, measurement: 528 g / mol)

[Synthesis Example 50] Synthesis of A-50

The procedure of Synthetic Example 49 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-50 , Yield: 71%).

Mass (theory: 529.65 g / mol, measurement: 529 g / mol)

[Synthesis Example 51] Synthesis of A-51

The procedure of Synthesis Example 49 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The target compound A-51 (4.5 g, yield 78%) was obtained.

Mass (theory: 530.64 g / mol, measured: 530 g / mol)

[Synthesis Example 52] Synthesis of A-52

The procedure of Synthetic Example 49 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine, 52 (3.9 g, yield 60%).

Mass (theory: 605.75 g / mol, measurement: 605 g / mol)

[Synthesis Example 53] Synthesis of A-53

Except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine (4.3 g, yield 66%) of the desired compound A-53.

Mass (theory: 606.74 g / mol, measurement: 665 g / mol)

[Synthesis Example 54] Synthesis of A-54

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-54 (5.3 g, yield 73%) was obtained in the same manner as in Synthetic Example 49.

Mass (theory: 682.83 g / mol, measured: 682 g / mol)

[Synthesis Example 55] Synthesis of A-55

(3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t-Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-55 (3.7 g, 65 %).

Mass (theory: 528.66 g / mol, measurement: 528 g / mol)

[Synthesis Example 56] Synthesis of A-56

The procedure of Synthesis Example 55 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-56 , Yield: 71%).

Mass (theory: 529.65 g / mol, measurement: 529 g / mol)

[Synthesis Example 57] Synthesis of A-57

The same procedure as in Synthesis Example 55 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-57 (4.5 g, yield 78%) was obtained.

Mass (theory: 530.64 g / mol, measured: 530 g / mol)

[Synthesis Example 58] Synthesis of A-58

The procedure of Synthetic Example 55 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine, 58 (3.9 g, yield 60%).

Mass (theory: 605.75 g / mol, measurement: 605 g / mol)

[Synthesis Example 59] Synthesis of A-59

Was prepared in the same manner as in Synthesis Example 55 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the target compound A-59 (4.3 g, yield 66%).

Mass (theory: 606.74 g / mol, measurement: 665 g / mol)

[Synthesis Example 60] Synthesis of A-60

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-60 (5.3 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 55.

Mass (theory: 682.83 g / mol, measured: 682 g / mol)

[Synthesis Example 61] Synthesis of A-61

(3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t-Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-61 (3.7 g, 65 %).

Mass (theory: 528.66 g / mol, measurement: 528 g / mol)

[Synthesis Example 62] Synthesis of A-62

The procedure of Synthesis Example 61 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-62 , Yield: 71%).

Mass (theory: 529.65 g / mol, measurement: 529 g / mol)

[Synthesis Example 63] Synthesis of A-63

The procedure of Synthesis Example 61 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective Compound A-63 (4.5 g, yield 78%) was obtained.

Mass (theory: 530.64 g / mol, measured: 530 g / mol)

[Synthesis Example 64] Synthesis of A-64

The procedure of Synthesis Example 61 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine, 64 (3.9 g, yield 60%).

Mass (theory: 605.75 g / mol, measurement: 605 g / mol)

[Synthesis Example 65] Synthesis of A-65

Was obtained in the same manner as in Synthesis Example 61, except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the target compound A-65 (4.3 g, yield 66%).

Mass (theory: 606.74 g / mol, measurement: 665 g / mol)

[Synthesis Example 66] Synthesis of A-66

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-66 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 61.

Mass (theory: 682.83 g / mol, measured: 682 g / mol)

[Synthesis Example 67] Synthesis of A-67

2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t- Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-67 (3.7 g, 65 %).

Mass (theory: 528.66 g / mol, measurement: 528 g / mol)

[Synthesis Example 68] Synthesis of A-68

The procedure of Synthesis Example 67 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-68 , Yield: 71%).

Mass (theory: 529.65 g / mol, measurement: 529 g / mol)

[Synthesis Example 69] Synthesis of A-69

The same procedure was followed as in Synthesis Example 67 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-69 (4.5 g, yield 78%) was obtained.

Mass (theory: 530.64 g / mol, measured: 530 g / mol)

[Synthesis Example 70] Synthesis of A-70

The procedure of Synthesis Example 67 was repeated except for using 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) instead of 2-chloro-4,6-diphenylpyridine, 70 (3.9 g, yield 60%).

Mass (theory: 605.75 g / mol, measurement: 605 g / mol)

[Synthesis Example 71] Synthesis of A-71

Was obtained in the same manner as in Synthesis Example 67 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the target compound A-71 (4.3 g, yield 66%).

Mass (theory: 606.74 g / mol, measurement: 665 g / mol)

[Synthesis Example 72] Synthesis of A-72

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-72 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 67.

Mass (theory: 682.83 g / mol, measured: 682 g / mol)

[Synthesis Example 73] Synthesis of A-73

(3.5 g, 9.76 mmol), 2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t- Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-73 (3.7 g, 65 %).

Mass (theory: 512.60 g / mol, measurement: 512 g / mol)

[Synthesis Example 74] Synthesis of A-74

The same procedure as in Synthesis Example 73 was carried out, except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine, , Yield: 71%).

Mass (theory: 513.59 g / mol, measurement: 513 g / mol)

[Synthesis Example 75] Synthesis of A-75

The same procedure was followed as in Synthesis Example 73 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-75 (4.5 g, yield 78%) was obtained.

Mass (theory: 514.58 g / mol, measurement: 514 g / mol)

[Synthesis Example 76] Synthesis of A-76

The procedure of Synthetic Example 73 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6- 76 (3.9 g, yield 60%).

Mass (theory: 589.68 g / mol, measurement: 589 g / mol)

[Synthesis Example 77] Synthesis of A-77

Except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the target compound A-77 (4.3 g, yield 66%).

Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[Synthesis Example 78] Synthesis of A-78

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-78 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 73.

Mass (theory: 666.77 g / mol, measurement: 666 g / mol)

[Synthesis Example 79] Synthesis of A-79

(3.5 g, 9.76 mmol), 2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-79 (3.7 g, 65 %).

Mass (theory: 512.60 g / mol, measurement: 512 g / mol)

[Synthesis Example 80] Synthesis of A-80

The procedure of Synthesis Example 79 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-80 , Yield: 71%).

Mass (theory: 513.59 g / mol, measurement: 513 g / mol)

[Synthesis Example 81] Synthesis of A-81

The procedure of Synthesis Example 79 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-81 (4.5 g, yield 78%) was obtained.

Mass (theory: 514.58 g / mol, measurement: 514 g / mol)

[Synthesis Example 82] Synthesis of A-82

The procedure of Synthetic Example 79 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine. 82 (3.9 g, yield 60%).

Mass (theory: 589.68 g / mol, measurement: 589 g / mol)

[Synthesis Example 83] Synthesis of A-83

Was obtained in the same manner as in Synthesis Example 79 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the target compound A-83 (4.3 g, yield 66%).

Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[Synthesis Example 84] Synthesis of A-84

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-84 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 79.

Mass (theory: 666.77 g / mol, measurement: 666 g / mol)

[Synthesis Example 85] Synthesis of A-85

(3.5 g, 9.76 mmol), 2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-85 (3.7 g, 65 %).

Mass (theory: 512.60 g / mol, measurement: 512 g / mol)

[Synthesis Example 86] Synthesis of A-86

The procedure of Synthetic Example 85 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-86 , Yield: 71%).

Mass (theory: 513.59 g / mol, measurement: 513 g / mol)

[Synthesis Example 87] Synthesis of A-87

The same procedure as in Synthesis Example 85 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective Compound A-87 (4.5 g, yield 78%) was obtained.

Mass (theory: 514.58 g / mol, measurement: 514 g / mol)

[Synthesis Example 88] Synthesis of A-88

The procedure of Synthesis Example 85 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6- 88 (3.9 g, yield 60%).

Mass (theory: 589.68 g / mol, measurement: 589 g / mol)

[Synthesis Example 89] Synthesis of A-89

Was obtained in the same manner as in Synthesis Example 85 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was carried out to obtain the target compound A-89 (4.3 g, yield 66%).

Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[Synthesis Example 90] Synthesis of A-90

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-90 (5.3 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 85.

Mass (theory: 666.77 g / mol, measurement: 666 g / mol)

[Synthesis Example 91] Synthesis of A-91

(3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t-Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-91 (3.7 g, 65 %).

Mass (theory: 512.60 g / mol, measurement: 512 g / mol)

[Synthesis Example 92] Synthesis of A-92

The procedure of Synthesis Example 91 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain target compound A-92 , Yield: 71%).

Mass (theory: 513.59 g / mol, measurement: 513 g / mol)

[Synthesis Example 93] Synthesis of A-93

The same procedure as in Synthesis Example 91 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective compound A-93 (4.5 g, yield 78%) was obtained.

Mass (theory: 514.58 g / mol, measurement: 514 g / mol)

[Synthesis Example 94] Synthesis of A-94

The procedure of Synthesis Example 91 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine, 94 (3.9 g, yield 60%).

Mass (theory: 589.68 g / mol, measurement: 589 g / mol)

[Synthesis Example 95] Synthesis of A-95

Was obtained in the same manner as in Synthesis Example 91 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the title compound A-95 (4.3 g, yield 66%).

Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[Synthesis Example 96] Synthesis of A-96

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-96 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 91.

Mass (theory: 666.77 g / mol, measurement: 666 g / mol)

[Synthesis Example 97] Synthesis of A-97

(3.5 g, 9.76 mmol), 2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t- Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound A-97 (3.7 g, 65 %).

Mass (theory: 512.60 g / mol, measurement: 512 g / mol)

[Synthesis Example 98] Synthesis of A-98

The procedure of Synthesis Example 97 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-98 , Yield: 71%).

Mass (theory: 513.59 g / mol, measurement: 513 g / mol)

[Synthesis Example 99] Synthesis of A-99

The procedure of Synthesis Example 97 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective Compound A-99 (4.5 g, yield 78%) was obtained.

Mass (theory: 514.58 g / mol, measurement: 514 g / mol)

[Synthesis Example 100] Synthesis of A-100

The procedure of Synthesis Example 97 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine, 100 (3.9 g, yield 60%).

Mass (theory: 589.68 g / mol, measurement: 589 g / mol)

[Synthesis Example 101] Synthesis of A-101

Was prepared in the same manner as in Synthesis Example 97, except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine Was performed to obtain the target compound A-101 (4.3 g, yield 66%).

Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[Synthesis Example 102] Synthesis of A-102

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-102 (5.3 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 97.

Mass (theory: 666.77 g / mol, measurement: 666 g / mol)

[Synthesis Example 103] Synthesis of A-103

2-chloro-4,6-diphenylpyridine (3.1 g, 11.7 mmol), Pd (OAc) ₂ (110 mg, 0.488 mmol), NaO (t- Bu) (1.9 g, 19.5 mmol), P (t-Bu) ₃ (50 wt%) (395 mg, 0.976 mmol) and Toluene (35 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and then water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain the desired compound A-103 (3.7 g, 65%).

Mass (theory: 512.60 g / mol, measurement: 512 g / mol)

[Synthesis Example 104] Synthesis of A-104

The procedure of Synthesis Example 103 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine to obtain the desired compound A-104 , Yield: 71%).

Mass (theory: 513.59 g / mol, measurement: 513 g / mol)

[Synthesis Example 105] Synthesis of A-105

The same procedure as in Synthesis Example 103 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine The objective Compound A-105 (4.5 g, yield 78%) was obtained.

Mass (theory: 514.58 g / mol, measurement: 514 g / mol)

[Synthesis Example 106] Synthesis of A-106

The procedure of Synthesis Example 103 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.0 g, 11.7 mmol) was used instead of 2-chloro-4,6-diphenylpyridine, 106 (3.9 g, yield 60%).

Mass (theory: 589.68 g / mol, measurement: 589 g / mol)

[Synthesis Example 107] Synthesis of A-107

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.0 g, 11.7 mmol) was used in place of 2-chloro-4,6-diphenylpyridine The desired compound A-107 (4.3 g, yield 66%) was obtained.

Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[Synthesis Example 108] Synthesis of A-108

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.9 g, 11.7 mmol), the target compound A-108 (5.3 g, yield 73%) was obtained in the same manner as in Synthesis Example 103.

Mass (theory: 666.77 g / mol, measurement: 666 g / mol)

[Synthesis Example 109] Synthesis of B-1

4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the desired compound B-1 (3.5 g, yield 66%).

Mass (theory value: 780.33, measurement value: 780 g / mol)

[Synthesis Example 110] Synthesis of B-2

The same procedure as in Synthesis Example 109 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound B-2 (3.4 g, yield 65%).

Mass (theory: 781.32, measurement: 781 g / mol)

[Synthesis Example 111] Synthesis of B-3

Was obtained in the same manner as in Synthesis Example 109 except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound B-3 (3.7 g, yield 64%).

Mass (theory: 857.35, measured: 857 g / mol)

[Synthesis Example 112] Synthesis of B-4

The procedure of Synthesis Example 109 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound B-4 70%).

Mass (theory: 754.31, measurement: 754 g / mol)

[Synthesis Example 113] Synthesis of B-5

The same procedure as in Synthesis Example 109 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound B-5 (3.7 g, yield 62%).

Mass (theory value: 880.36, measurement value: 880 g / mol)

[Synthesis Example 114] Synthesis of B-6

(2.0 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol) and 1,10-phenanthroline mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound B-6 (3.2 g, yield 64%).

Mass (theory: 754.27, found: 754 g / mol)

[Synthesis Example 115] Synthesis of B-7

The same procedure was followed as in Synthesis Example 114 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound B-7 (3.5 g, yield 69%).

Mass (theory: 755.27, measurement: 755 g / mol)

[Synthesis Example 116] Synthesis of B-8

The same procedure as in Preparation Example 114 was repeated, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine. To obtain the desired compound B-8 (3.4 g, yield 61%).

Mass (theory: 831.30, measurement: 831 g / mol)

[Synthesis Example 117] Synthesis of B-9

The procedure of Synthesis Example 114 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain 3.1 g 63%).

Mass (theory: 728.26, measurement: 728 g / mol)

[Synthesis Example 118] Synthesis of B-10

The procedure of Synthesis Example 114 was repeated except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the title compound B-10 (3.8 g, yield 66%).

Mass (theory: 854.30, measurement: 854 g / mol)

[Synthesis Example 119] Synthesis of C-1

(3.6 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound C-1 (3.3 g, yield 63%).

Mass (theory: 770.25, measurement: 770 g / mol)

[Synthesis Example 120] Synthesis of C-2

The same procedure was followed as in Synthesis Example 119 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine To obtain the aimed compound C-2 (3.6 g, yield 70%).

Mass (theory: 771.25, measurement: 771 g / mol)

[Synthesis Example 121] Synthesis of C-3

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound C-3 (3.7 g, yield 65%).

Mass (theory: 847.28, measurement: 847 g / mol)

[Synthesis Example 122] Synthesis of C-4

The procedure of Synthesis Example 119 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain 3.1 g 63%).

Mass (calcd.: 744.23, found: 744 g / mol)

[Synthesis Example 123] Synthesis of C-5

The same procedure as in Synthesis Example 119 was performed except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the aimed compound C-5 (3.8 g, yield 66%).

Mass (theory: 870.28, measured: 870 g / mol)

[Synthesis Example 124] Synthesis of D-1

4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the desired compound D-1 (3.2 g, yield 61%).

Mass (theory value: 780.33, measurement value: 780 g / mol)

[Synthesis Example 125] Synthesis of D-2

The same procedure as in Synthesis Example 124 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound D-2 (3.4 g, yield 65%).

Mass (theory: 781.32, measurement: 781 g / mol)

[Synthesis Example 126] Synthesis of D-3

Was obtained in the same manner as in Synthesis Example 124 except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound D-3 (3.6 g, yield 63%).

Mass (theory: 857.35, measured: 857 g / mol)

[Synthesis Example 127] Synthesis of D-4

The procedure of Synthesis Example 124 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound D-4 62%).

Mass (theory: 754.31, measurement: 754 g / mol)

[Synthesis Example 128] Synthesis of D-5

The same procedure as in Synthesis Example 124 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound D-5 (4.0 g, yield 68%).

Mass (theory value: 880.36, measurement value: 880 g / mol)

[Synthesis Example 129] Synthesis of E-1

(2.0 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound E-1 (3.3 g, yield 65%).

Mass (theory: 754.27, found: 754 g / mol)

[Synthesis Example 130] Synthesis of E-2

The procedure of Synthesis Example 129 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine The objective Compound E-2 (3.2 g, yield 63%) was obtained.

Mass (theory: 755.27, measurement: 755 g / mol)

[Synthesis Example 131] Synthesis of E-3

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound E-3 (3.7 g, yield 67%).

Mass (theory: 831.30, measurement: 831 g / mol)

[Synthesis Example 132] Synthesis of E-4

The procedure of Synthesis Example 129 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound E-4 (3.4 g, yield 70%).

Mass (theory: 728.26, measurement: 728 g / mol)

[Synthesis Example 133] Synthesis of E-5

The same procedure as in Synthesis Example 129 was performed except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound E-5 (4.2 g, yield 73%).

Mass (theory: 854.30, measurement: 854 g / mol)

[Synthesis Example 134] Synthesis of F-1

(3.6 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol) and 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain the desired compound F-1 (3.3 g, yield 64%).

Mass (theory: 770.25, measurement: 770 g / mol)

[Synthesis Example 135] Synthesis of F-2

The same procedure as in Synthesis Example 134 was performed except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine To obtain the aimed compound F-2 (3.3 g, yield 63%).

Mass (theory: 771.25, measurement: 771 g / mol)

[Synthesis Example 136] Synthesis of F-3

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound F-3 (3.8 g, yield 67%).

Mass (theory: 847.28, measurement: 847 g / mol)

[Synthesis Example 137] Synthesis of F-4

The procedure of Synthesis Example 134 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine to obtain 3.1 g 62%).

Mass (calcd.: 744.23, found: 744 g / mol)

[Synthesis Example 138] Synthesis of F-5

The same procedure as in Synthesis Example 134 was repeated, except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound F-5 (3.8 g, yield 66%).

Mass (theory: 870.28, measured: 870 g / mol)

[Synthesis Example 139] Synthesis of G-1

4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain the desired compound G-1 (3.9 g, yield 71%).

Mass (theory: 829.32, measurement: 829 g / mol)

[Synthesis Example 140] Synthesis of G-2

The same procedure as in Synthesis Example 139 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound G-2 (4.1 g, yield 73%).

Mass (theory: 830.32, measurement: 830 g / mol)

[Synthesis Example 141] Synthesis of G-3

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound G-3 (3.9 g, yield 64%).

Mass (theory: 905.35, measurement: 905 g / mol)

[Synthesis Example 142] Synthesis of G-4

The procedure of Synthesis Example 139 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound G-4 (3.4 g, 64%).

Mass (theory: 803.30, measurement: 803 g / mol)

[Synthesis Example 143] Synthesis of G-5

The same procedure as in Synthesis Example 139 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound G-5 (4.1 g, yield 66%).

Mass (theory: 929.35, found: 929 g / mol)

[Synthesis Example 144] Synthesis of H-1

To a solution of AzC-8 (4.0 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain the desired compound H-1 (3.6 g, yield 64%).

Mass (theory: 829.32, measurement: 829 g / mol)

[Synthesis Example 145] Synthesis of H-2

The same procedure was followed as in Synthesis Example 144 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound H-2 (3.9 g, yield 70%).

Mass (theory: 830.32, measurement: 830 g / mol)

[Synthesis Example 146] Synthesis of H-3

The same procedure as in Synthesis Example 144 was repeated, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the target compound H-3 (4.3 g, yield 71%).

Mass (theory: 905.35, measurement: 905 g / mol)

[Synthesis Example 147] Synthesis of H-4

The procedure of Synthesis Example 144 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound H-4 (3.5 g, yield 65%).

Mass (theory: 803.95, measurement: 803 g / mol)

[Synthesis Example 148] Synthesis of H-5

The same procedure as in Synthesis Example 144 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain objective compound H-5 (3.7 g, yield 60%).

Mass (theory: 929.35, found: 929 g / mol)

[Synthesis Example 149] Synthesis of I-1

(3.5 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the desired compound I-1 (3.2 g, yield 63%).

Mass (theory: 754.27, found: 754 g / mol)

[Synthesis Example 150] Synthesis of I-2

The same procedure as in Preparation Example 149 was repeated but using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) instead of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound I-2 (3.4 g, yield 67%).

Mass (theory: 755.27, measurement: 755 g / mol)

[Synthesis Example 151] Synthesis of I-3

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound I-3 (3.4 g, yield 61%).

Mass (theory: 830.30, measured: 830 g / mol)

[Synthesis Example 152] Synthesis of I-4

The same procedure as in Synthesis Example 149 was repeated but using 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound I- 70%).

Mass (theory: 728.26, measurement: 728 g / mol)

[Synthesis Example 153] Synthesis of I-5

The same procedure as in Preparation Example 149 was repeated, except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound I-5 (4.2 g, yield 73%).

Mass (theory: 854.30, measurement: 854 g / mol)

[Synthesis Example 154] Synthesis of J-1

(3.2 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain the desired compound J-1 (3.0 g, yield 64%).

Mass (theory: 705.28, measured: 705 g / mol)

[Synthesis Example 155] Synthesis of J-2

The same procedure as in Synthesis Example 154 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine To obtain the title compound J-2 (3.4 g, yield 71%).

Mass (theory: 706.27, measurement: 706 g / mol)

[Synthesis Example 156] Synthesis of J-3

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound J-3 (3.7 g, yield 70%).

Mass (theory: 782.30, measured: 782 g / mol)

[Synthesis Example 157] Synthesis of J-4

The procedure of Synthesis Example 154 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound J-4 (2.9 g, 63%).

Mass (theory: 679.26, found: 679 g / mol)

[Synthesis Example 158] Synthesis of J-5

The same procedure as in Synthesis Example 154 was performed except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound J-5 (3.6 g, yield 66%).

Mass (theory: 805.31, measurement: 805 g / mol)

[Synthesis Example 159] Synthesis of K-1

(3.0 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain the desired compound K-1 (3.0 g, yield 67%).

Mass (theory: 679.23, measurement: 679 g / mol)

[Synthesis Example 160] Synthesis of K-2

The same procedure as in Synthesis Example 159 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound K-2 (2.9 g, yield 64%).

Mass (theory: 680.22, measurement: 680 g / mol)

[Synthesis Example 161] Synthesis of K-3

The same procedure as in Preparation Example 159 was repeated but using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound K-3 (3.2 g, yield 63%).

Mass (theory: 756.25, measurement: 756 g / mol)

[Synthesis Example 162] Synthesis of K-4

The procedure of Synthesis Example 159 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound K-4 (2.9 g, 67%).

Mass (theory: 653.21, found: 653 g / mol)

[Synthesis Example 163] Synthesis of K-5

The same procedure as in Synthesis Example 159 was repeated but using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 4-bromo-2,6-diphenylpyrimidine To obtain the aimed compound K-5 (3.2 g, yield 61%).

Mass (theory: 779.26, measurement: 779 g / mol)

[Synthesis Example 164] Synthesis of L-1

(3.1 g, 6.7 mmol), 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the desired compound L-1 (2.9 g, yield 63%).

Mass (theory: 695.20, measurement: 695 g / mol)

[Synthesis Example 165] Synthesis of L-2

The same procedure was followed as in Synthesis Example 164 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.14 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound L-2 (2.8 g, yield 61%).

Mass (theory: 696.20, measurement: 696 g / mol)

[Synthesis Example 166] Synthesis of L-3

Was obtained in the same manner as in Preparation Example 164 except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound L-3 (3.5 g, yield 67%).

Mass (theory: 777.23, measurement: 777 g / mol)

[Synthesis Example 167] Synthesis of L-4

The procedure of Synthetic Example 164 was repeated except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 4-bromo-2,6-diphenylpyrimidine to obtain the desired compound L-4 (2.8 g, 62%).

Mass (theory: 669.19, found: 669 g / mol)

[Synthesis Example 168] Synthesis of L-5

The same procedure as in Synthesis Example 164 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) was used in place of 4-bromo-2,6-diphenylpyrimidine To obtain the desired compound L-5 (3.8 g, yield 71%).

Mass (theory: 795.23, measured: 795 g / mol)

[Synthesis Example 169] Synthesis of M-1

(2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1 ' -bromo- (1, 1 &apos;, 3 &apos;, 1 ") terphenyl (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred for 3 hours at 210 ° C. After completion of the reaction, , And then purified by column chromatography to obtain the title compound M-1 (3.4 g, yield 65%).

Mass (theory: 778.33, measurement: 778 g / mol)

[Synthesis Example 170] Synthesis of M-2

The procedure of Synthesis Example 169 was repeated except that 4-bromobiphenyl (1.90 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3', 1 " (3.1 g, yield 66%).

Mass (theory: 702.30, measurement: 702 g / mol)

[Synthesis Example 171] Synthesis of M-3

Except that 2-bromo-9,9-dimethyl-9H-fluorene (2.18 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3' The same procedure was followed to obtain the title compound M-3 (3.1 g, yield 63%).

Mass (theory: 742.33, measurement: 742 g / mol)

[Synthesis Example 172] Synthesis of N-1

(2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1 ' -bromo- (1,1 &apos;, 3 &apos;, 1 ") terphenyl (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred for 3 hours at 210 ° C. After completion of the reaction, , And then purified by column chromatography to obtain the title compound N-1 (3.4 g, yield 66%).

Mass (theory: 778.33, measurement: 778 g / mol)

[Synthesis Example 173] Synthesis of N-2

The procedure of Synthesis Example 172 was repeated except that 4-bromobiphenyl (1.90 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3', 1 " (3.1 g, yield 66%).

Mass (theory: 702.30, measurement: 702 g / mol)

[Synthesis Example 174] Synthesis of N-3

Except that 2-bromo-9,9-dimethyl-9H-fluorene (2.18 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3' The objective compound N-3 (3.0 g, yield 60%) was obtained by carrying out the same procedure.

Mass (theory: 742.33, measurement: 742 g / mol)

[Synthesis Example 175] Synthesis of O-1

(3.5 g, 6.7 mmol), 5'-bromo- (1,1 ', 3', 1 ") terphenyl (2.5 g, 8.0 mmol), CuI (0.13 g, (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred for 3 hours at 210 ° C. After completion of the reaction, , And then purified by column chromatography to obtain the desired compound O-1 (3.2 g, yield 64%).

Mass (theory: 752.28, measured: 752 g / mol)

[Synthesis Example 176] Synthesis of O-2

The procedure of Synthesis Example 175 was repeated except that 4-bromobiphenyl (1.90 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3', 1 " (3.1 g, yield 68%).

Mass (theory: 675.26, measured: 675 g / mol)

[Synthesis Example 177] Synthesis of O-3

Except that 2-bromo-9,9-dimethyl-9H-fluorene (2.18 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3' The same procedure was followed to obtain the desired compound O-3 (3.0 g, yield 63%).

Mass (theory: 716.28, measurement: 716 g / mol)

[Synthesis Example 178] Synthesis of P-1

(2.5 g, 8.0 mmol), CuI (0.13 g, 0.67 mmol), 1 ' -bromo- (1,1 &apos;, 3 &apos;, 1 ") terphenyl (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred for 3 hours at 210 ° C. After completion of the reaction, , And then purified by column chromatography to obtain the target compound P-1 (3.2 g, yield 67%).

Mass (theory: 703.29, measured: 703 g / mol)

[Synthesis Example 179] Synthesis of P-2

The procedure of Synthesis Example 178 was repeated except that 4-bromobiphenyl (1.90 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3', 1 " (2.9 g, yield 70%).

Mass (theory: 627.26, found: 627 g / mol)

[Synthesis Example 180] Synthesis of P-3

Except that 2-bromo-9,9-dimethyl-9H-fluorene (2.18 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3' The same procedure was followed to obtain the desired compound P-3 (3.4 g, yield 76%).

Mass (theory: 667.29, found: 667 g / mol)

[Examples 1 to 144] Preparation of green organic electroluminescent device

Compounds synthesized in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method, and devices were manufactured according to the following procedure.

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

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent substrate (electrode) + host compound + 10% Ir (ppy) ₃ (30 nm) / BCP Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

[Comparative Example 1] Production of green organic electroluminescent device

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

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , BCP and CBP used in Examples 1 to 144 and Comparative Example 1 are as follows.

[Evaluation Example 1]

The driving voltage, the current efficiency and the emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices prepared in Examples 1 to 144 and Comparative Example 1, and the results are shown in the following Table 1 .

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 A-1 6.70 518 41.5 Example 2 A-2 6.75 518 41.5 Example 3 A-3 6.48 516 41.4 Example 4 A-4 6.86 518 41.2 Example 5 A-5 6.60 517 41.1 Example 6 A-6 6.50 516 42.5 Example 7 A-7 6.75 517 39.8 Example 8 A-8 6.66 515 41.3 Example 9 A-9 6.65 518 40.4 Example 10 A-10 6.60 518 41.1 Example 11 A-11 6.70 516 41.3 Example 12 A-12 6.65 515 39.7 Example 13 A-13 6.70 518 41.1 Example 14 A-14 6.66 515 42.5 Example 15 A-15 6.65 516 42.4 Example 16 A-16 6.65 516 43.1 Example 17 A-17 6.64 515 41.2 Example 18 A-18 6.60 518 41.6 Example 19 A-19 6.70 518 42.5 Example 20 A-20 6.71 517 39.2 Example 21 A-21 6.61 516 41.3 Example 22 A-22 6.50 517 39.7 Example 23 A-23 6.73 516 41.1 Example 24 A-24 6.61 518 41.3 Example 25 A-25 6.63 518 39.7 Example 26 A-26 6.62 517 41.1 Example 27 A-27 6.70 515 42.5 Example 28 A-28 6.60 516 40.1 Example 29 A-29 6.50 518 41.8 Example 30 A-30 6.63 517 41.7 Example 31 A-31 6.55 516 42.9 Example 32 A-32 6.61 515 41.6 Example 33 A-33 6.63 517 40.7 Example 34 A-34 6.70 517 41.2 Example 35 A-35 6.61 518 40.7 Example 36 A-36 6.63 517 41.1 Example 37 A-37 6.70 516 42.0 Example 38 A-38 6.65 518 41.5 Example 39 A-39 6.50 518 41.4 Example 40 A-40 6.86 518 41.2 Example 41 A-41 6.55 517 41.1 Example 42 A-42 6.51 516 42.5 Example 43 A-43 6.60 517 41.8 Example 44 A-44 6.66 515 41.3 Example 45 A-45 6.60 518 39.7 Example 46 A-46 6.65 518 41.1 Example 47 A-47 6.55 517 41.3 Example 48 A-48 6.65 516 40.9 Example 49 A-49 6.50 515 41.1 Example 50 A-50 6.66 515 42.5 Example 51 A-51 6.65 515 42.5 Example 52 A-52 6.65 515 43.1 Example 53 A-53 6.60 515 41.2 Example 54 A-54 6.45 518 41.4 Example 55 A-55 6.71 518 42.5 Example 56 A-56 6.73 517 41.2 Example 57 A-57 6.61 516 41.3 Example 58 A-58 6.60 517 42.7 Example 59 A-59 6.60 515 41.1 Example 60 A-60 6.61 518 41.3 Example 61 A-61 6.63 518 42.0 Example 62 A-62 6.62 517 41.1 Example 63 A-63 6.70 515 42.1 Example 64 A-64 6.55 516 40.1 Example 65 A-65 6.63 518 40.8 Example 66 A-66 6.60 517 41.7 Example 67 A-67 6.55 516 42.9 Example 68 A-68 6.50 515 41.6 Example 69 A-69 6.63 515 40.7 Example 70 A-70 6.70 518 41.3 Example 71 A-71 6.61 518 41.9 Example 72 A-72 6.50 517 42.1 Example 73 A-73 6.72 516 41.5 Example 74 A-74 6.70 518 41.8 Example 75 A-75 6.48 518 41.4 Example 76 A-76 6.50 518 41.2 Example 77 A-77 6.61 517 41.6 Example 78 A-78 6.51 515 42.5 Example 79 A-79 6.60 517 41.2 Example 80 A-80 6.66 515 41.3 Example 81 A-81 6.65 518 42.6 Example 82 A-82 6.55 518 41.1 Example 83 A-83 6.60 517 41.3 Example 84 A-84 6.65 518 42.4 Example 85 A-85 6.55 515 41.1 Example 86 A-86 6.66 515 42.5 Example 87 A-87 6.60 515 42.5 Example 88 A-88 6.65 516 43.1 Example 89 A-89 6.70 515 41.2 Example 90 A-90 6.61 518 41.1 Example 91 A-91 6.55 518 42.5 Example 92 A-92 6.60 517 40.8 Example 93 A-93 6.50 515 41.3 Example 94 A-94 6.63 517 42.1 Example 95 A-95 6.70 515 41.1 Example 96 A-96 6.60 518 41.6 Example 97 A-97 6.66 516 41.3 Example 98 A-98 6.62 517 41.9 Example 99 A-99 6.55 515 42.1 Example 100 A-100 6.60 516 40.9 Example 101 A-101 6.63 518 40.8 Example 102 A-102 6.60 517 41.7 Example 103 A-103 6.50 516 42.8 Example 104 A-104 6.61 515 41.6 Example 105 A-105 6.55 515 40.7 Example 106 A-106 6.73 517 41.7 Example 107 A-107 6.61 518 42.7 Example 108 A-108 6.60 517 41.9 Example 109 B-1 6.72 515 41.5 Example 110 B-2 6.75 518 41.5 Example 111 B-3 6.48 518 41.4 Example 112 B-6 6.86 518 41.2 Example 113 Synthesis of B-7 6.61 517 41.1 Example 114 B-8 6.51 515 42.5 Example 115 C-1 6.77 517 39.2 Example 116 C-2 6.66 515 41.3 Example 117 C-3 6.65 518 39.7 Example 118 D-1 6.65 518 41.1 Example 119 D-2 6.77 517 41.3 Example 120 D-3 6.65 515 39.7 Example 121 E-1 6.77 515 41.1 Example 122 E-2 6.66 515 42.5 Example 123 E-3 6.65 515 42.5 Example 124 F-1 6.65 515 43.1 Example 125 F-2 6.64 515 41.2 Example 126 F-3 6.61 518 41.1 Example 127 G-1 6.7 518 42.5 Example 128 G-2 6.73 517 39.2 Example 129 G-3 6.61 515 41.3 Example 130 H-1 6.63 517 39.7 Example 131 H-2 6.73 515 41.1 Example 132 H-3 6.61 518 41.3 Example 133 I-1 6.63 518 39.7 Example 134 I-2 6.62 517 41.1 Example 135 I-3 6.73 515 42.5 Example 136 J-1 6.61 515 40.1 Example 137 J-2 6.63 518 40.8 Example 138 J-3 6.63 517 40.7 Example 139 K-1 6.62 515 42.9 Example 140 K-2 6.61 515 39.6 Example 141 K-3 6.63 515 40.7 Example 142 [ L-1 6.73 518 41.3 Example 143 L-2 6.61 518 39.7 Example 144 L-3 6.63 517 41.1 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound according to the present invention was used for the light emitting layer of the green organic electroluminescent device (Examples 1 to 144), the conventional CBP was used for the light emitting layer of the green organic electroluminescent device (Comparative Example 1) It was confirmed that the efficiency and the driving voltage were superior.

[Examples 145 to 168] Preparation of red organic electroluminescent device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.

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

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent substrate (electrode) + host compound + 10% (piq) ₂ Ir (acac) (30 nm) / BCP nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm).

[Comparative Example 2]

A device was fabricated in the same manner as in Example 145 except that CBP was used instead of Compound B-4 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, BCP and CBP used in Examples 145 to 168 and Comparative Example 2 are as described above, and the structure of (piq) ₂ Ir (acac) is as follows.

[Evaluation Example 2]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each red organic electroluminescent device manufactured in Examples 145 to 168 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 145 B-4 4.76 10.1 Example 146 B-5 4.64 12.7 Example 147 B-9 4.55 13.1 Example 148 B-10 4.68 10.1 Example 149 C-4 4.55 9.2 Example 150 C-5 4.32 9.2 Example 151 D-4 4.74 11.5 Example 152 D-5 4.87 9.2 Example 153 E-4 4.53 9.2 Example 154 E-5 4.55 11.5 Example 155 F-4 4.68 11.8 Example 156 F-5 4.35 11.5 Example 157 G-4 4.53 11.8 Example 158 G-5 4.55 9.6 Example 159 H-4 4.65 9.7 Example 160 H-5 4.74 9.1 Example 161 I-4 4.87 9.1 Example 162 I-5 4.56 9.2 Example 163 J-4 4.65 9.2 Example 164 J-5 4.55 11.5 Example 165 K-4 4.68 9.2 Example 166 K-5 4.35 9.1 Example 167 L-4 4.55 9.2 Example 168 L-5 4.32 13.2 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound of the present invention was used for the light emitting layer of the red organic electroluminescent device (Examples 145 to 168), the conventional CBP was used for the light emitting layer of the red organic electroluminescent device (Comparative Example 2) It was confirmed that the efficiency and the driving voltage were excellent.

[Examples 169 to 180] Preparation of blue organic electroluminescent device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a blue organic electroluminescent device was fabricated according to the following procedure.

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

(15 nm) / ADN + 5% DS-405 (Doosan) (manufactured by Doosan Heavy Industries, Ltd.) on the ITO transparent electrode prepared above 300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device. At this time, the compounds shown in the following Table 3 were used as materials for the light emission-assisting layer, the structure of BCP was as described above, and the structures of ADN and NPB were as follows.

[Comparative Example 3] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was produced in the same manner as in Example 169 except that the compound M-1 was not used as the luminescent auxiliary layer material in the luminescent layer formation.

[Evaluation Example 3]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices manufactured in Examples 169 to 180 and Comparative Example 3, and the results are shown in Table 3 below.

Sample The light- The driving voltage (V) Current efficiency (cd / A) Example 169 M-1 5.50 6.90 Example 170 M-2 5.55 6.80 Example 171 M-3 5.40 6.50 Example 172 N-1 5.45 6.55 Example 173 N-2 5.45 6.70 Example 174 N-3 5.50 6.75 Example 175 O-1 5.50 6.80 Example 176 O-2 5.40 6.65 Example 177 O-3 5.40 6.60 Example 178 P-1 5.45 6.70 Example 179 P-2 5.55 6.80 Example 180 P-3 5.40 6.80 Comparative Example 3 _ 5.60 4.80

As shown in Table 3, when the compound of the present invention was used for the light-emission-assisting layer of the blue organic electroluminescent device (Examples 169 to 180), the efficiency and the driving voltage of the blue organic electroluminescent device .

Claims (11)

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

In Formula 1,
X ₁ is selected from the group consisting of O, S and N (Ar ₁ )
Ar ₁ is a C ₆ to C ₁₅ aryl group,
At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ forms a condensed ring represented by the following formula (2)
(2)

In Formula 2,
The dotted line is a moiety which is condensed with the above-mentioned formula (1)
X ₂ is N (R ₃₁ )
R ₁ to R ₄ which do not form a condensed ring of Formula 2; R ₅ to R ₁₄ are each independently hydrogen,
R ₃₁ is selected from the group consisting of a C ₆ to C ₁₂ aryl group and a heteroaryl group having 5 to 10 nuclear atoms,
The aryl group and the heteroaryl group of R ₃₁ may be substituted or unsubstituted with at least one substituent selected from the group consisting of C ₆ aryl group and heteroaryl group having 5 to 6 nuclear atoms,
The heteroaryl group contains 1 to 3 heteroatoms, wherein the heteroatom is at least one selected from the group consisting of N, O and S. The method according to claim 1,
Wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (1a) to (1f):
[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

&Lt; RTI ID = 0.0 &

[Formula 1e]

(1f)

In the above general formulas (1a) to (1f)
X ₁ , X ₂ , R ₁ to R ₁₄ are as defined in claim 1. A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X ₁ is N (Ar ₁ )
Ar ₁ is selected from the group consisting of a C ₆ to C ₁₅ aryl group and a heteroaryl group having 5 to 10 nuclear atoms,
R ₂ and R ₃ form a condensed ring represented by the following formula (2)
(2)

In Formula 2,
The dotted line is a moiety which is condensed with the above-mentioned formula (1)
X ₂ is selected from the group consisting of O, S, N (R ₃₁ ) and C (R ₃₂ ) (R ₃₃ )
R ₁ , R ₄ to R ₇ , R ₉ to R ₁₀ , and R ₁₁ to R ₁₄ are each independently hydrogen,
R ₃₁ is a C ₆ to C ₁₂ aryl group and a heteroaryl group having 5 to 10 nuclear atoms,
R ₃₂ to R ₃₃ are each independently a C ₁ alkyl group,
In Formula 1, R ₈ is represented by the following Formula 3,
(3)

In Formula 3,
* Is a moiety connected to the formula (1)
L &lt; ₁ &gt; is a single bond,
One of R ₂₁ to R ₂₈ is connected to the formula (1), and each of R ₂₁ to R _{28, which} is not connected to L ₁ , is independently hydrogen,
X ₃ is selected from the group consisting of O and N (R ₃₁ )
R ₃₁ is a C ₆ to C ₁₂ aryl group and a heteroaryl group having 5 to 10 nuclear atoms,
The aryl group of said Ar ₁ and heteroaryl groups are each independently C ₆ ~ C ₁₀ aryl group, and the number of nuclear atoms which may be unsubstituted or substituted by one substituent at least one selected from the group consisting of a heteroaryl group of from 5 to 6,
The heteroaryl groups each independently have 1 to 3 heteroatoms, wherein the heteroatom is at least one selected from the group consisting of N, O, and S. delete delete delete The method according to claim 1 or 3,
Wherein Ar ₁ and R ₃₁ are each independently a phenyl group. The method according to claim 1 or 3,
Wherein Ar ₁ and R ₃₁ are each independently selected from the group consisting of the structures represented by the following formulas A1 to A10.

In the above-mentioned A1 to A10,
L ₂ is selected from the group consisting of a single bond and a C ₆ to C ₁₂ arylene group,
R ₁₅ is selected from the group consisting of hydrogen, and a group of C ₆ aryl, each independently,
R ₄₁ is hydrogen, n is an integer of 1 to 4,
Wherein R ₁₅ is an aryl group may be unsubstituted or substituted by one substituent at least one selected from the group consisting of each independently an aryl group of C ₆ ~ C _10. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 3. 10. The method of claim 9,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, and a light emitting layer. 10. The method of claim 9,
Wherein the organic compound layer containing the compound is a phosphorescent light-emitting layer.