KR20180055206A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to organic compounds and to an organic electroluminescent device comprising the same. According to the present invention, the organic compounds can improve light emitting efficiency, driving voltage, lifespan and the like of the organic electroluminescent device by being used in an organic layer, desirably a light emitting layer, an electron transporting layer or an electron transporting auxiliary layer of the organic electroluminescent device.

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 that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

The electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 were followed up with the observation of organic thin film emission from Bernanose in the 1950s. In 1987, Tang The organic light emitting device having a laminated structure in which the hole layer and the functional layer of the light emitting layer are divided. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the 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. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

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

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescence, the phosphorescent dopant as well as phosphorescent host materials are being studied extensively.

To date, NPB, BCP and Alq ₃ have been widely known as the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.

However, conventional organic material layers are advantageous from the viewpoint of light emitting properties, but their thermal stability is not very good due to their low glass transition temperature, and thus they are not satisfactory in terms of lifetime of the organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.

It is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and which is excellent in hole, electron injection, transporting ability, and light emitting ability.

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

In order to achieve the above object, the present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

X ₁ is selected from the group consisting of S, O, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ );

X ₂ and X ₃ are each independently N or C (Ar ₄ );

Ring A is represented by any one of the following formulas (2) to (4);

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,

The dotted line means the part where the condensation is made;

m is an integer from 0 to 4;

n is an integer from 0 to 6;

Ar ₁ to Ar ₄ and R ₁ are each independently a substituent represented by the following formula (5), and when a plurality of R _{1 s} are present, they are the same or different;

[Chemical Formula 5]

In Formula 5,

* Denotes the part where the bond is made;

L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;

R ₂ is 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 cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

Wherein L ₁ and the L ₂ arylene group and a heteroarylene group, an alkyl group of the R _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, 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 alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

The present invention provides an organic electroluminescent device including 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 one or more compounds represented by Formula 1 .

"Alkyl" in the present invention is a monovalent substituent derived 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, but are not limited thereto.

As used herein, the term " alkenyl " is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.

The term " alkynyl " in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, , 2-propynyl, and the like, but are not limited thereto.

&Quot; Aryl " in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as, for example, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, Click ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, " aryloxy " means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

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

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

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

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

&Quot; Alkylsilyl " in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and " arylsilyl " means silyl substituted with aryl having 5 to 60 carbon atoms.

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

Since the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.

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

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel compounds of the present invention can be represented by the following formula

[Chemical Formula 1]

In Formula 1,

X ₁ is selected from the group consisting of S, O, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ );

X ₂ and X ₃ are each independently N or C (Ar ₄ );

Ring A is represented by any one of the following formulas (2) to (4);

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,

The dotted line means the part where the condensation is made;

m is an integer from 0 to 4;

n is an integer from 0 to 6;

Ar ₁ to Ar ₄ and R ₁ are each independently a substituent represented by the following formula (5), and when a plurality of R _{1 s} are present, they are the same or different;

 [Chemical Formula 5]

In Formula 5,

* Denotes the part where the bond is made;

L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;

R ₂ is 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 cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

Wherein L ₁ and the L ₂ arylene group and a heteroarylene group, an alkyl group of the R _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, 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 alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

In the present invention, when R ₁ is represented by the general formula (5), L ₁ and L ₂ are simultaneously a direct bond and R ₂ is hydrogen.

The organic compound of the present invention is a compound having, as a basic skeleton, a structure in which one or more substituents connected directly or via a linker group are connected to a moiety to which a 5-membered aromatic ring or a 5-membered aromatic heterocycle is bonded, Can be displayed.

In the present invention, the 5-membered aromatic ring or the 5-membered aromatic heterocycle may be, but not limited to, an indole moiety, an indazole moiety, an indene moiety, a benzofuran moiety, a benzo-thiophene,

More specifically, the compound represented by the formula (1) of the present invention is a compound in which EWG is bonded to a five-membered aromatic ring or a five-membered aromatic heterocycle such as indole, indazole indene, benzofuran, benzothiophene, triazole, Since it has an energy level similar to that of the sol, it can be adjusted to a higher level than the energy level of the dopant and is applicable as a host material. Particularly, since the moiety of benzo furan and benzo-thiophene is abundant in electrons, the mobility of the benzo-furan and the benzo-thiophene is high when used as an electron transport layer material of the organic electroluminescent device, so that the luminous efficiency can be increased and the driving voltage can be reduced. Since the 5-membered aromatic ring or 5-membered aromatic heterocycle of the present invention has a lower molecular weight than that of the conventional compound, the deposition can be performed at a relatively lower temperature than the materials having different deposition temperatures at the time of deposition, .

Therefore, the compound represented by the general formula (1) of the present invention can be suitably used for an organic electroluminescent device organic material layer, preferably a light emitting layer material (green phosphorescent host material), an electron transporting layer / injection layer material luminescent auxiliary layer material, Preferably used as a light emitting layer material, an electron injecting layer material, and an electron transporting layer material. In addition, the organic electroluminescent device including the compound of Formula 1 can be greatly improved in performance and lifetime, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize its performance.

According to a preferred embodiment of the present invention, the compound may be represented by any one of the following formulas (6) to (11):

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above formulas 6 to 11,

Each of Ring A and Ar ₁ to Ar ₄ is as defined in Formula 1 above.

According to a preferred embodiment of the present invention, the compound represented by any one of the above formulas (6) and (8) to (11) is preferable for ensuring low driving voltage and high luminous efficiency, And more preferably represented by the above general formula (8) or (10).

According to a preferred embodiment of the present invention, each of Ar ₁ to Ar ₄ is independently a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms,

The aryl group and the heteroaryl group of Ar ₁ to Ar ₄ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ arylamine group, a C ₆ to C ₆₀ aryl group, A heteroaryl group, and when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ to Ar ₄ each independently represent a phenyl group, a biphenyl group, a naphthalenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranoyl group, , A carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxinyl group,

The aryl group of Ar ₁ to Ar ₄ is preferably a phenyl group, a biphenyl group, a naphthalenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group And dibenzodioxinyl groups are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ arylamine group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms Optionally substituted with one or more selected substituents, and when substituted with a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, Ar ₁ to Ar ₄ each independently represent a phenyl group, a biphenyl group, a naphthalenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranoyl group, , A carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxinyl group,

The aryl group of Ar ₁ to Ar ₄ is preferably a phenyl group, a biphenyl group, a naphthalenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group And dibenzodioxinyl groups are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, naphthalenyl, pyridinyl, pyrimidinyl, Benzothiophenyl group, carbazolyl group, fluorenyl group, spirofluorenyl group and dibenzodioxinyl group, and when they are substituted with a plurality of substituents, they may be the same or different from each other Can be different.

According to a preferred embodiment of the present invention, each of L ₁ and L ₂ is independently a direct bond or a linker represented by any one of the following formulas A-1 to A-6, but is not limited thereto:

In the above Formulas A-1 to A-6,

* Denotes the part where the bond is made;

Z ₁ to Z ₈ are each independently N or C (Ar ₅ );

Any two of Z ₁ to Z ₆ bonded as a linker in the above formula (A-1) are C (Ar ₅ ), wherein Ar ₅ is a member;

Any one of Z ₁ to Z ₄ and any of Z ₅ to Z ₈ which is bonded as a linker in the above formula (A-3) is C (Ar ₅ ), wherein Ar ₅ is a member;

Any two of Z ₁ to Z ₄ bonded as a linker in the above formula (A-4) are C (Ar ₅ ), wherein Ar ₅ is a member;

X ₅ and X ₆ are each independently O, S, N (Ar ₆ ) or C (Ar ₇ ) (Ar ₈ );

X ₇ is N or C (Ar ₉ );

Ar ₅ to Ar ₉ 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, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a group that is selected or adjacent from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ bond to form a condensed ring, and said Ar ₅ To Ar ₈ are plural, they are the same or different from each other;

Alkyl groups of the Ar ₅ to Ar _9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, each of L ₁ and L ₂ is independently a direct bond or a linker represented by any one of the following formulas B-1 to B-11, but is not limited thereto:

In the above Formulas B-1 to B-11,

* Denotes the part where the bond is made;

Ar ₆ to Ar ₉ 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, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl groups of the Ar ₆ to Ar _9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, in the formulas (B-1) to (B-11), Ar ₆ to Ar ₉ each independently represents hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A heteroaryl group having 5 to 60 nuclear atoms;

The alkyl group, aryl group and heteroaryl group of Ar ₆ to Ar ₉ are each independently 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 ₆ to C ₆₀ An aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of Formulas B-1, B-2 and B-6 to B-11.

According to a preferred embodiment of the present invention, R ₂ may be a substituent represented by the following general formula (12):

[Chemical Formula 12]

In Formula 12,

* Denotes the part where the bond is made;

Y ₁ to Y ₅ are each independently N or C (Ar ₁₀ );

Ar ₁₀ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of is selected from the group consisting of aryl amine group, when the Ar ₁₀ are the same or different, and plural individual these;

Alkyl groups of the Ar _10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _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 C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphazene group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the Is optionally substituted on a substituent group, if substituted to a plurality of substituents, they are same as or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by the formula (12) may be a substituent represented by the following formula (13)

[Chemical Formula 13]

In Formula 13,

* Denotes the part where the bond is made;

R ₃ and R ₄ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl group of the R ₃ and R _4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with a plurality of substituents, they are the same as or different from each other;

Each of Z ₁ , Z ₃ and Z ₅ is as defined in the above formula (12).

According to a preferred embodiment of the present invention, the substituent represented by the formula (12) may be a substituent represented by any one of the following formulas (B-1) to (B-3)

In the above formulas C-1 to C-5,

* Denotes the part where the bond is made,

R ₃ and R ₄ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl group of the R ₃ and R _4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₃ and R ₄ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms Selected,

The alkyl, aryl and heteroaryl groups of R ₃ and R ₄ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₃ and R ₄ each independently represent a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group , ≪ / RTI >

Of the R ₃ and R ₄ A phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group And a heteroaryl group having 5 to 60 nuclear atoms, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₃ and R ₄ each independently represent a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group , ≪ / RTI >

Of the R ₃ and R ₄ The phenyl group, the biphenyl group, the pyridinyl group, the pyrimidinyl group, the dibenzofuranyl group, the carbazolyl group, the fluorenyl group and the dibenzothiophenyl group are each independently a methyl group, an ethyl group, a propionyl group, When substituted with one or more substituents selected from the group consisting of a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group, and when they are substituted with a plurality of substituents, They are the same or different.

According to a preferred embodiment of the present invention, R ₂ may be a substituent represented by the following formula (14):

[Chemical Formula 14]

In Formula 14,

* Denotes the part where the bond is made;

R ₅ and R ₆ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 aryl phosphazene group, selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring;

Alkyl groups of the R ₅ and R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₅ and R ₆ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms Selected,

The alkyl, aryl and heteroaryl groups of R ₅ and R ₆ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₅ and R ₆ are each independently a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group , ≪ / RTI >

The R ₅ and R ₆ A phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group And a heteroaryl group having 5 to 60 nuclear atoms, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₅ and R ₆ are each independently a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group , ≪ / RTI >

The R ₅ and R ₆ The phenyl group, the biphenyl group, the pyridinyl group, the pyrimidinyl group, the dibenzofuranyl group, the carbazolyl group, the fluorenyl group and the dibenzothiophenyl group are each independently a methyl group, an ethyl group, a propionyl group, When substituted with one or more substituents selected from the group consisting of a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group and a dibenzothiophenyl group, and when they are substituted with a plurality of substituents, They are the same or different.

The compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:

The compounds of general formula (I) of the present invention can be synthesized according to the general synthetic method (Chem Rev, 60: 313 ( 1960); J. Chem SOC 4482 (1955); Chem Rev. 95:..... 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic Field  Light emitting element

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used singly or in combination of two or more.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI >

The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, referring to FIG. 1, an anode 10 and a cathode 20 facing each other, 20). ≪ / RTI > Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. A hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32. An electron transporting auxiliary layer 35 may be interposed between the electron transporting layer 34 and the light emitting layer 32 can do.

2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).

In the present invention, the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO. The layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.

The electron injecting layer 36 is a layer which is stacked on the electron transporting layer to facilitate injection of electrons from the cathode to ultimately improve the power efficiency. For example, LiF, Liq, NaCl, CsF, Li ₂ O, BaO, or the like can be used.

In addition, although not shown in the drawings, the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32. The light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32. The light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.

In addition, although not shown in the drawings, a life improving layer may be further included between the electron transporting auxiliary layer 35 and the light emitting layer 32. Holes moving in the organic light emitting device due to the ionization potential level in the light emitting layer 32 are blocked by the high energy barrier of the lifetime enhancing layer and do not diffuse or move to the electron transporting layer and consequently function to limit the holes to the light emitting layer . The function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .

In the present invention, the compound represented by the general formula (1) is a compound in which EWG is bonded to a five-membered aromatic ring or a five-membered aromatic hetero ring such as indole, indazole indene, benzofuran, benzothiophene or triazole, It can be adjusted to a higher level than the energy level of the dopant and can be applied as a host material. Particularly, since the moiety of benzofuran and benzothiophene is rich in electrons, the mobility of the electron transport layer material of the organic electroluminescent device is increased, so that the luminous efficiency and the driving voltage can be reduced. Since the 5-membered aromatic ring or 5-membered aromatic heterocycle of the present invention has a lower molecular weight than that of the conventional compound, the deposition can be performed at a relatively lower temperature than the materials having different deposition temperatures at the time of deposition, .

Accordingly, the compound represented by the formula (1) of the present invention can be used as any one of a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer which are organic compound layers of an organic electroluminescent device. Transporting layer and an electron transporting layer, and more preferably an electron transporting layer, or an electron transporting layer.

When the compound according to the present invention is used as a light emitting layer material, specifically, the compound represented by the above formula (1) can be used as a phosphorescent host, a fluorescent host or a dopant material of a light emitting layer, preferably a phosphorescent host And / or a red phosphorescent host material).

In addition, the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.

The organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 To form another organic material layer and an electrode.

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

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

The anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, 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 or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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 A1

(24.4 mmol) of l- (3-bromophenyl) -1H-indazole, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- A solution of 7.4 g (29.2 mmol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of KOAc, and 1,4-dioxane (200 ml) were mixed and stirred at 130 캜 for 6 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 target compound A1 (5.5 g, 17.1 mmol, yield 70%).

GC-Mass (theoretical value: 320.19 g / mol, measurement: 320 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 ~ 7.55 (m, 4H), 7.62 ~ 7.74 (m, 3H), 7.92 (d, 1H), 8.17 (d, 1H), 8.35 (s, 1H )

[ Preparation Example  2] Synthesis of A2

(24.4 mmol) of l- (3-bromophenyl) -3-phenyl-1H-indazole and 4 g of 4,4,4 ', 4', 5,5,5 & 7.4 g (29.2 mmol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of KOAc and 7.2 g (73.1 mmol) of Pd 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 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 A2 (6.8 g, 17. 1 mmol, yield 70%).

GC-Mass (calculated: 369.29 g / mol, measured: 369 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 ~ 7.58 (m, 7H), 7.62 ~ 7.77 (m, 5H), 7.92 (d, 1H), 8.17 (d, 1H)

[ Preparation Example  3] Synthesis of A3

8.5 g (24.4 mmol) of 4,4,4 ', 4', 5,5,5 ' -methyl-3- (pyridin- , 7.4 g (29.2 mol) of 5'-octamethyl-2,2' -bis (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g 73.1 mmol) and 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After the 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 target compound A3 (7.3 g, 18.3 mmol, yield 75%).

GC-Mass (theory: 397.28 g / mol, measurement: 397 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 ~ 7.55 (m, 4H), 7.62 ~ 7.79 (m, 5H), 7.92 (d, 1H), 8.17 (d, 1H), 8.71 ~ 8.72 (m , 2H)

[ Preparation Example  4] Synthesis of A4

(24.4 mmol) of l- (3-bromophenyl) -5-phenyl-1H-indazole and 4 g of 4,4,4 ', 4', 5,5,5 & 7.4 g (29.2 mol) of Pd (dppf) Cl _2, 0.6 g (0.7 mmol) of KOAc, 7.2 g (73.1 mmol) of 1, 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the objective compound A4 (7.2 g, 18.3 mmol, yield 75%).

GC-Mass (calculated: 396.29 g / mol, measured: 396 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 7.43-7.59 (m, 7H), 7.62-7.74 (m, 3H), 7.92 )

[ Preparation Example  5] Synthesis of A5

8.5 g (24.4 mmol) of 4,4,4 ', 4', 5,5,5 '- tetramethylpiperidine were added to a solution of 1- (3-bromophenyl) , 7.4 g (29.2 mol) of 5'-octamethyl-2,2' -bis (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g 73.1 mmol) and 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 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 target compound A5 (7.5 g, 19.0 mmol, yield 78%).

GC-Mass (theory: 397.28 g / mol, measurement: 397 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 7.43-7.59 (m, 4H), 7.62-7.74 (m, 3H), 7.92 ), 8.71-8.72 (m, 2H)

[ Preparation Example  6] Synthesis of A6

(24.4 mmol) of l- (3-bromophenyl) -3,5-diphenyl-1H-indazole and 4,4,4 ', 4', 5,5,5 ' 7.4 g (29.2 mol) of octamethyl-2,2' -bis (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 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 A6 (9.0 g, 19.0 mmol, yield 78%).

GC-Mass (theory: 472.39 g / mol, measured: 472 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.41 ~ 7.58 (m, 10H), 7.63 ~ 7.77 (m, 5H), 7.92 (d, 1H), 8.17 (d, 1H)

[ Preparation Example  7] Synthesis of A7

(24.4 mmol) of 5- (3-bromophenyl) -1-phenyl-1H-indazole, 4,4,4 ', 4', 5,5,5 & 7.4 g (29.2 mol) of Pd (dppf) Cl _2, 0.6 g (0.7 mmol) of KOAc, 7.2 g (73.1 mmol) of 1, 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 hours.

After the 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 target compound A7 (6.3 g, 18.0 mmol, yield 74%).

GC-Mass (calculated: 369.29 g / mol, measured: 369 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 7.45 (s, 1H), 7.47-7.62 (m, 9H), 8.01

[ Preparation Example  8] Synthesis of A8

10.4 g (24.4 mmol) of 4,4,4 ', 4', 5,5,5 ', 5 ' 7.4 g (29.2 mol) of octamethyl-2,2' -bis (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A8 (8.1 g, 18.0 mmol, yield 74%).

GC-Mass (theory: 472.39 g / mol, measured: 472 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 7.45 (s, 1H), 7.47-7.62 (m, 12H), 7.88-7.89 )

[ Preparation Example  9] Synthesis of A9

8.5 g (24.4 mmol) of 4,4,4 ', 4', 5,5,5 ' -methyl-5- (3-bromophenyl) , 7.4 g (29.2 mol) of 5'-octamethyl-2,2' -bis (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g 73.1 mmol) and 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the desired compound A9 (6.8 g, 18.0 mmol, yield 74%).

GC-Mass (theory: 397.28 g / mol, measurement: 397 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 7.45 (s, 1H), 7.47-7.62 (m, 6H), 8.01 8.45-8.46 (m, 2H)

[ Preparation Example  10] Synthesis of A10

(17.4 g, 24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5', 5,5'-tetramethyluronium hexafluorophosphate 7.4 g (29.2 mol) of octamethyl-2,2' -bis (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the title compound A10 (14.1 g, 18.0 mmol, yield 74%).

GC-Mass (calculated: 779.73 g / mol, measured: 779 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 7.45 (s, 1H), 7.47-7.58 (m, 14H), 7.62-7.70 ), 8.08 (s, IH), 8.17 (d, IH), 8.24-8.30 (m, 6H), 8.32

[ Preparation Example  11] Synthesis of A11

(24.4 mmol) of 3- (3-bromophenyl) -3H-benzo [e] indazole, 4,4,4 ', 4', 5,5,5 & 7.4 g (29.2 mol) of Pd (dppf) Cl _2, 0.6 g (0.7 mmol) of KOAc, 7.2 g (73.1 mmol) of 1, 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 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 target compound A11 (6.3 g, 17.1 mmol, yield 70%).

GC-Mass (theory: 370.25 g / mol, measurement: 370 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 (s, 1H), 7.47 ~ 7.62 (m, 5H), 7.75 (d, 1H), 8.18 ~ 8.33 (m, 3H), 8.35 (s, 1H )

[ Preparation Example  12] Synthesis of A12

(24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5', 5'-biphenyl-3H-benzo [ 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of Pd (dppf) Cl ₂ and 7.2 g ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the desired compound A12 (7.6 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 446.35 g / mol, measured: 446 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 (s, 1H), 7.45 ~ 7.62 (m, 8H), 7.75 (d, 1H), 7.74 ~ 7.75 (m, 2H), 8.18 ~ 8.33 (m , 3H)

[ Preparation Example  13] Synthesis of A13

(24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5', 5'-tetramethylpiperidine 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of Pd (dppf) Cl ₂ and 7.2 g ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A13 (7.6 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 446.35 g / mol, measured: 446 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 ~ 7.62 (m, 8H), 7.65 (s, 1H), 7.75 (d, 1H), 8.18 ~ 8.33 (m, 4H), 8.35 (s, 1H )

[ Preparation Example  14] Synthesis of A14

(24.4 mmol) of 4,4,4 ', 4-tetrafluorobenzene were added to a solution of 3- (3-bromophenyl) -1-phenyl-8- ', 5,5,5', 5'-octamethyl-2,2'-(1,3,2- dioxa view it is) 7.4 g (29.2 mol), Pd (dppf) Cl 2 0.6 g ( 0.7 mmol), KOAc 7.2 g (73.1 mmol) and 1,4-dioxane (200 ml) were mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A14 (8.9 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 523.43 g / mol, measured: 523 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 (s, 1H), 7.45 ~ 7.62 (m, 9H), 7.75 (d, 1H), 7.74 ~ 7.75 (m, 2H), 8.18 ~ 8.33 (m , 3H), 8.55-8.56 (m, 2H)

[ Preparation Example  15] Synthesis of A15

(19.4 g, 24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-tetramethyl-3- 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of Pd (dppf) Cl ₂ and 7.2 g ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A15 (15.8 g, 19.0 mmol, yield 78%).

GC-Mass (theory: 829.79 g / mol, measurement: 829 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 ~ 7.62 (m, 12H), 7.65 (s, 1H), 7.72 (s, 1H), 7.74 (s, 1H), 7.75 (d, 1H), (S, 1H), 8.18-8.35 (m, 7H), 8.35 (s, 1H)

[ Preparation Example  16] Synthesis of A16

(24.4 mmol) of l- (3-bromophenyl) -1H-benzo [f] indazole, 4,4,4 ', 4', 5,5,5 ' 7.4 g (29.2 mol) of Pd (dppf) Cl _2, 0.6 g (0.7 mmol) of KOAc, 7.2 g (73.1 mmol) of 1, 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain the desired compound A16 (6.3 g, 17.1 mmol, yield 70%).

GC-Mass (theory: 370.25 g / mol, measurement: 370 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 7.44 (s, 1H), 7.45-7.61 (m, 4H), 7.65 8.18-8.19 (m, 2H), 8.35 (s, 1 H)

[ Preparation Example  17] Synthesis of A17

(24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5', 5'-bis (trifluoromethyl) 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of Pd (dppf) Cl ₂ and 7.2 g ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the desired compound A17 (7.6 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 446.35 g / mol, measured: 446 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.44 (s, 1H), 7.45 ~ 7.61 (m, 6H), 7.61 (s, 1H), 7.65 (s, 1H), 7.66 (s, 1H), 1H), 7.75 (d, 1H), 8.18-8.19 (m, 2H), 8.35

[ Preparation Example  18] Synthesis of A18

(19.4 g, 24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-tetramethyl-3- 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of Pd (dppf) Cl ₂ and 7.2 g ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After the completion of the reaction, the reaction mixture was extracted with ethyl acetate, and then dried over MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A18 (15.8 g, 19.0 mmol, yield 78%).

GC-Mass (theory: 829.79 g / mol, measurement: 829 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.44 (s, 1H), 7.43 ~ 7.61 (m, 11H), 7.61 (s, 1H), 7.65 (s, 1H), 7.66 (s, 1H), 1H), 7.75 (s, 1H), 7.74 (s, 1H), 7.74 (s,

[ Preparation Example  19] Synthesis of A19

(24.4 mmol) of l- (3-bromophenyl) -1H-benzo [g] indazole, 4,4,4 ', 4', 5,5,5 ' 7.4 g (29.2 mol) of Pd (dppf) Cl _2, 0.6 g (0.7 mmol) of KOAc, 7.2 g (73.1 mmol) of 1, 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain the desired compound A19 (6.3 g, 17.1 mmol, yield 70%).

GC-Mass (theory: 370.25 g / mol, measurement: 370 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.27 (d, 1H), 7.44 (s, 1H), 7.48 ~ 7.61 (m, 4H), 7.75 (d, 1H), 7.92 (d, 1 H) , 8.16 (d, IH), 8.35 (s, IH), 8.55 (d, IH)

[ Preparation Example  20] Synthesis of A20

(24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5', 5'-biphenyl- 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of Pd (dppf) Cl ₂ and 7.2 g ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A20 (7.6 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 446.35 g / mol, measured: 446 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.27 (d, 1H), 7.44 (s, 1H), 7.48 ~ 7.61 (m, 8H), 7.62 (s, 1H), 7.66 (s, 1H), 7.71 (d, 1H), 7.91 (d, 1H), 8.35 (s, 1H)

[ Preparation Example  21] Synthesis of A21

(19.4 g, 24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-tetramethyl-3- 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of Pd (dppf) Cl ₂ and 7.2 g ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 hours.

After the 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 target compound A21 (15.8 g, 19.0 mmol, yield 78%).

GC-Mass (theory: 829.79 g / mol, measurement: 829 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.27 (d, 1H), 7.44 (s, 1H), 7.44 ~ 7.61 (m, 17H), 7.62 (s, 1H), 7.66 (s, 1H), (M, 5H), 8.35 (d, 1H), 7.69 (s, 1H) (s, 1 H)

[ Preparation Example  22] Synthesis of A22

(24.4 mmol) of l- (3-bromophenyl) -1H-indazole, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (73.1 mmol) of KOAc and 14 g of 1,4-dioxane (200 ml) were mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain the desired compound A22 (5.4 g, 17.1 mmol, yield 70%).

GC-Mass (theory: 319.21 g / mol, measurement: 319 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 6.55 ~ 6.78 (m, 2H), 7.42 (s, 1H), 7.45 ~ 7.61 (m, 4H), 7.75 ~ 7,91 (m, 3H)

[ Preparation Example  23] Synthesis of A23

(24.4 mmol) of l- (3-bromophenyl) -3-phenyl-1H-indazole and 4 g of 4,4,4 ', 4', 5,5,5 & 7.4 g (29.2 mol) of Pd (dppf) Cl _2, 0.6 g (0.7 mmol) of KOAc, 7.2 g (73.1 mmol) of 1, 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A23 (6.7 g, 17.1 mmol, yield 70%).

GC-Mass (theory: 395.30 g / mol, measurement: 395 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 7.32 (s, IH), 7.42 (s, IH), 7.46-7.65

[ Preparation Example  24] Synthesis of A24

(24.4 mmol) of l- (3-bromophenyl) -5-phenyl-1H-indazole and 4 g of 4,4,4 ', 4', 5,5,5 & 7.4 g (29.2 mol) of Pd (dppf) Cl _2, 0.6 g (0.7 mmol) of KOAc, 7.2 g (73.1 mmol) of 1, 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A24 (7.2 g, 18.3 mmol, yield 75%).

GC-Mass (theory: 395.30 g / mol, measurement: 395 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 6.50 (d, 1H), 7.44 (s, 1H), 7.48 ~ 7.61 (m, 9H), 7.75 (s, 1 H), 8.08 ~ 8.15 (m, 2H)

[ Preparation Example  25] Synthesis of A24

17.9 g (24.4 mmol) of Y1, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2' -bis (1,3,2-dioxabo 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of KOAc, and 200 ml of 1,4-dioxane were mixed and heated at 130 ° C for 6 hours Lt; / RTI >

After the 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 target compound A25 (14.2 g, 18.3 mmol, yield 75%).

GC-Mass (calculated: 778.75 g / mol, measured: 778 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 6.51 (d, 1H), 7.44-7.61 (m, 18H), 7.65 ), 7.76 (s, 1H), 8.08 (s, 1H), 8.12-8.25 (m, 7H)

[ Preparation Example  26] Synthesis of A26

(24.4 mmol) of l- (3-bromophenyl) -1H-indazole, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (73.1 mmol) of KOAc and 14 g of 1,4-dioxane (200 ml) were mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A26 (6.3 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 369.26 g / mol, measured: 369 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 6.51 (d, 1H), 7.44 (s, 1H), 7.48 ~ 7.61 (m, 7H), 8.02 ~ 8.10 (d, 3H)

[ Preparation Example  27] Synthesis of A27

(24.4 mmol) of l- (3-bromophenyl) -3-phenyl-1H-indazole, 4,4,4 ', 4', 5,5,5 & 7.4 g (29.2 mol) of Pd (dppf) Cl _2, 0.6 g (0.7 mmol) of KOAc, 7.2 g (73.1 mmol) of 1, 4-dioxane (200 ml) was mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO ₄ to obtain the target compound A27 (6.3 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 369.26 g / mol, measured: 369 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 6.51 (d, IH), 7.40 (s, IH), 7.43-7.55 ), 8.08-8.10 (d, 2H)

[ Preparation Example  28] Synthesis of A28

(24.4 mmol) of l- (3-bromophenyl) -1H-indazole, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- 7.4 g (29.2 mol) of Pd (dppf) Cl ₂ , 0.7 g (73.1 mmol) of KOAc and 14 g of 1,4-dioxane (200 ml) were mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A28 (6.3 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 369.26 g / mol, measured: 369 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 6.51 (d, 1H), 7.40 (s, 1H), 7.43 ~ 7.55 (m, 3H), 7.69 ~ 7.79 (m, 4H), 8.08 ~ 8.22 (d , 3H)

[ Preparation Example  29] Synthesis of A29

(24.4 mmol) of 5- (3-bromophenyl) benzofuran, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'- 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) of KOAc and 200 ml of 1,4-dioxane ) Were mixed and stirred at 130 DEG C for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography using MgSO ₄ to obtain the target compound A29 (5.5 g, 17.1 mmol, yield 70%).

GC-Mass (calculated: 369.26 g / mol, measured: 369 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 6.65 (d, 1H), 7.55 ~ 7.59 (m, 3H), 7.65 (s, 1H), 7.70 (s, 1H), 7.72 ~ 7.79 (m, 3H )

[ Preparation Example  30] Synthesis of A30

7.3 g (24.4 mmol) of 5- (3-bromophenyl) -1,1-dimethyl-1H-indene and 4,4,4,4 ', 4', 5,5,5 & 7.4 g (29.2 mol) of methyl-2,2' -bis (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g , And 4-dioxane (200 ml) were mixed and stirred at 130 ° C for 6 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 A30 (5.9 g, 17.1 mmol, yield 70%).

GC-Mass (theory: 346.27 g / mol, measurement: 346 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 1.69 (s, 6H), 6.65 (d, 1H), 7.55-7.59 7.72 ~ 7.79 (m, 3H)

[ Preparation Example  31] Synthesis of A31

(24.4 mmol) of 5- (3-bromophenyl) benzo [b] thiophene, 4,4,4 ', 4', 5,5,5 ' 7.4 g (29.2 mol) of 2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (200 ml) were mixed and stirred at 130 캜 for 6 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was extracted with MgSO _{4. The} residue was purified by column chromatography to obtain the target compound A31 (6.1 g, 18.3 mmol, yield 75%).

GC-Mass (theory: 336.26 g / mol, measurement: 326 g / mol)

¹ H-NMR :? 1.25 (s, 12H), 6.65 (d, 1H), 7.55-7.59 (m, 3H), 7.69 )

[ Preparation Example  32] Synthesis of A32

(24.4 mmol) of l- (3-bromophenyl) -1H-indazole, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- A solution of 7.4 g (29.2 mmol) of Pd (dppf) Cl ₂ , 0.7 g (0.7 mmol) of KOAc, and 1,4-dioxane (200 ml) were mixed and stirred at 130 캜 for 6 hours.

After the 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 A32 (5.5 g, 17.1 mmol, yield 70%).

GC-Mass (theory: 321.18 g / mol, measured: 321 g / mol)

^{1 H-NMR: δ 1.25 (} s, 12H), 7.45 ~ 7.54 (m, 4H), 7.62 ~ 7.74 (m, 3H), 7.92 (d, 1H), 8.16 (d, 1H)

[ Synthetic example  1] Synthesis of R7

(17.1 mmol) of A1, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the organic layer solvent, the residue was purified by column chromatography to obtain the target compound R7 (7.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 577.68 g / mol, measured: 577 g / mol)

[ Synthetic example  2] Synthesis of R10

(Dibenzo [b, d] furan-4-yl) -1,3,5-triazine, 9.2 g (18.8 mmol) of A1, ), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and potassium carbonate, 7.1 g (51.2 mmol) of toluene / H ₂ O / ethanol in an amount of 80 ml / 40 ml / 40 ml and stirred at 110 ° C. for 3 hours Respectively.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the organic layer solvent, the residue was purified by column chromatography to obtain the target compound R10, (7.7 g, 12.8 mmol, yield 75%).

GC-Mass (theory: 605.64 g / mol, measurement: 605 g / mol)

[ Synthetic example  3] Synthesis of R13

5.5 g (17.1 mmol) of A1, 2- (7- (3-bromophenyl) -9,9-dimethyl-9H- fluoren- Pd (PPh ₃ ) ₄ , and potassium carbonate, 7.1 g (51.2 mmol) and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R13, (7.6 g, 12.8 mmol, yield 75%).

GC-Mass (theory: 617.74 g / mol, measured: 617 g / mol)

[ Synthetic example  4] Synthesis of R25

A mixture of 6.8 g (17.1 mmol) of A2, 7.3 g (18.8 mmol) of 4- (biphenyl-4-yl) -6-bromo-2-phenylpyrimidine, 1.0 g PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) and toluene / H ₂ O / ethanol in an amount of 80 ml / 40 ml / 40 ml, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R25 (7.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 576.69 g / mol, measured: 576 g / mol)

[ Synthetic example  5] Synthesis of R127

(6.8 g, 17.1 mmol), A2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R27 (8.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 653.77 g / mol, measured: 653 g / mol)

[ Synthetic example  6] Synthesis of R47

7.3 g (18.3 mmol) of A3 and 9.3 g (20.1 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ and potassium carbonate (7.6 g, 54.8 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were added thereto and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R47 (9.0 g, 13.7 mmol, yield 75%).

GC-Mass (calculated: 654.76 g / mol, measured: 654 g / mol)

[ Synthetic example  7] Synthesis of R67

7.2 g (18.3 mmol) of A4, 9.3 g (20.1 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ and potassium carbonate (7.6 g, 54.8 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were added thereto and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R67 (9.0 g, 13.7 mmol, yield 75%).

GC-Mass (calculated: 653.77 g / mol, measured: 653 g / mol)

[ Synthetic example  8] Synthesis of R87

(19.0 mmol) of A5, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol) Pd (PPh ₃ ) ₄ and potassium carbonate (7.9 g, 57.0 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removal of the organic layer solvent, the residue was purified by column chromatography to obtain the target compound R87 (9.3 g, 14.3 mmol, yield 75%).

GC-Mass (calculated: 654.76 g / mol, measured: 654 g / mol)

[ Synthetic example  9] Synthesis of R107

(19.0 mmol) of A6, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol) Pd (PPh ₃ ) ₄ and potassium carbonate (7.9 g, 57.0 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R107 (10.4 g, 14.3 mmol, yield 75%).

GC-Mass (729.87 g / mol, measured: 729 g / mol)

[ Synthetic example  10] Synthesis of R127

(17.1 mmol) of A7, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine and 8.7 g (18.8 mmol) of 1.0 Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R127 (8.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 653.77 g / mol, measured: 653 g / mol)

[ Synthetic example  11] Synthesis of R147

8.1 g (17.1 mmol) of A8, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R147 (8.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 654.76 g / mol, measured: 654 g / mol)

[ Synthetic example  12] Synthesis of R167

(6.8 g, 17.1 mmol), A 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the organic layer solvent, the residue was purified by column chromatography to obtain the target compound R167 (9.3 g, 12.4 mmol, yield 75%).

GC-Mass (729.87 g / mol, measured: 729 g / mol)

[ Synthetic example  13] Synthesis of R187

(18.0 mmol) of A10, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.2 g (19.8 mmol) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.5 g (54.1 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R187 (14.0, 13.5 mmol, yield 75%).

GC-Mass (theory: 1037.22 g / mol, measurement: 1037 g / mol)

[ Synthetic example  14] Synthesis of R207

(17.1 mmol) of A11, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R207 (8.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 627.73 g / mol, measured: 627 g / mol)

[ Synthetic example  15] Synthesis of R210

(Dibenzo [b, d] furan-4-yl) -1,3,5-triazine and 9.2 g (18.8 mmol) of A11 in a nitrogen stream. ), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and potassium carbonate, 7.1 g (51.2 mmol) of toluene / H ₂ O / ethanol in an amount of 80 ml / 40 ml / 40 ml and stirred at 110 ° C. for 3 hours Respectively.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R210 (8.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 655.70 g / mol, measured: 655 g / mol)

[ Synthetic example  16] Synthesis of R227

7.6 g (17.1 mmol) of A12, 8.7 g (18.8 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R227 (9.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 703.83 g / mol, measured: 703 g / mol)

[ Synthetic example  17] Synthesis of R247

8.9 g (17.1 mmol) of A13, 8.7 g (18.8 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R267 (10.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 780.91 g / mol, measured: 780 g / mol)

[ Synthetic example  18] Synthesis of R236

8.9 g (17.1 mmol) of A14, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R267 (10.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 780.91 g / mol, measured: 780 g / mol)

[ Synthetic example  19] Synthesis of R287

15.8 g (19.0 mmol) of A15, 9.7 g (20.9 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ and potassium carbonate (7.9 g, 57.0 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R287 (15.5 g, 14.3 mmol, yield 75%).

GC-Mass (theory: 1087.27 g / mol, measurement: 1087 g / mol)

[ Synthetic example  20] Synthesis of R307

(17.1 mmol) of A16, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R307 (8.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 627.73 g / mol, measured: 627 g / mol)

[ Synthetic example  21] Synthesis of R310

(Dibenzo [b, d] furan-4-yl) -1,3,5-triazine, 9.2 g (18.8 mmol) of A16 ), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and potassium carbonate, 7.1 g (51.2 mmol) of toluene / H ₂ O / ethanol in an amount of 80 ml / 40 ml / 40 ml and stirred at 110 ° C. for 3 hours Respectively.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R310 (8.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 655.70 g / mol, measured: 655 g / mol)

[ Synthetic example  22] Synthesis of R347

7.6 g (17.1 mmol) of A17 and 8.7 g (18.8 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R347 (9.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 703.83 g / mol, measured: 703 g / mol)

[ Synthetic example  23] Synthesis of R333

(19.9 mmol) of A18, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol) Pd (PPh ₃ ) ₄ and potassium carbonate (7.9 g, 57.0 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R367 (15.5 g, 14.3 mmol, yield 75%).

GC-Mass (theory: 1087.27 g / mol, measurement: 1087 g / mol)

[ Synthetic example  24] Synthesis of R387

(17.1 mmol) of A19, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine and 8.7 g (18.8 mmol) of 1.0 Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removal of the organic layer solvent, the residue was purified by column chromatography to obtain the target compound R387 (8.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 627.73 g / mol, measured: 627 g / mol)

[ Synthetic example  25] Synthesis of R390

(Dibenzo [b, d] furan-4-yl) -1,3,5-triazine, 9.2 g (18.8 mmol) of A16 ), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and potassium carbonate, 7.1 g (51.2 mmol) of toluene / H ₂ O / ethanol in an amount of 80 ml / 40 ml / 40 ml and stirred at 110 ° C. for 3 hours Respectively.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R390 (8.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 655.70 g / mol, measured: 655 g / mol)

[ Synthetic example  26] Synthesis of 407

7.6 g (17.1 mmol) of A17 and 8.7 g (18.8 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R407 (9.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 703.83 g / mol, measured: 703 g / mol)

[ Synthetic example  27] Synthesis of R427

(19.9 mmol) of A21, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol) Pd (PPh ₃ ) ₄ and potassium carbonate (7.9 g, 57.0 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R427 (15.5 g, 14.3 mmol, yield 75%).

GC-Mass (theory: 1087.27 g / mol, measurement: 1087 g / mol)

[ Synthetic example  28] 447

(17.8 mmol) of A22, 8.7 g (18.8 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R447 (7.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 576.69 g / mol, measured: 576 g / mol)

[ Synthetic example  29] 467

(17.8 mmol) of A23, 8.7 g (18.8 mmol) of 2, 3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the objective compound R467 (8.0 g, 12.3 mmol, yield 72%).

GC-Mass (calculated: 652.78 g / mol, measured: 652 g / mol)

[ Synthetic example  30] Synthesis of 487

7.2 g (18.3 mmol) of A24, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.3 g (20.1 mmol) Pd (PPh ₃ ) ₄ and potassium carbonate (7.6 g, 54.8 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were added thereto and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the organic layer solvent, the residue was purified by column chromatography to obtain the target compound R487 (8.6 g, 13.2 mmol, yield 72%).

GC-Mass (calculated: 652.78 g / mol, measured: 652 g / mol)

[ Synthetic example  31] 487

(18.3 mmol) of A25, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.3 g (20.1 mmol) Pd (PPh ₃ ) ₄ and potassium carbonate (7.6 g, 54.8 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were added thereto and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R507 (14.6 g, 13.2 mmol, yield 72%).

GC-Mass (calculated: 1112.32 g / mol, measured: 1112 g / mol)

[ Synthetic example  32] 527

(17.1 mmol) of A26, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R527 (8.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 626.75 g / mol, measured: 626 g / mol)

[ Synthetic example  33] 567

(17.8 mmol) of A27, 8.7 g (18.8 mmol) of 2, 3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R567 (8.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 626.75 g / mol, measured: 626 g / mol)

[ Synthetic example  34] 587

(17.8 mmol) of A27, 8.7 g (18.8 mmol) of 2, 3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R587 (8.0 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 626.75 g / mol, measured: 626 g / mol)

[ Synthetic example  35] 587

5.5 g (17.1 mmol) of A29, 8.7 g (18.8 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R607 (7.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 577.67 g / mol, measured: 577 g / mol)

[ Synthetic example  36] 587

5.9 g (17.1 mmol) of A30, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl- 1,3,5-triazine, 8.7 g Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol) of g (5 mol%) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R687 (7.4 g, 12.3 mmol, yield 72%).

GC-Mass (theory: 603.75 g / mol, measurement: 603 g / mol)

[ Synthetic example  37] Synthesis of 767

6.1 g (18.3 mmol) of A31 and 9.3 g (20.1 mmol) of 2- (3'-bromobiphenyl-3-yl) Pd (PPh ₃ ) ₄ and potassium carbonate (7.6 g, 54.8 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were added thereto and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R767 (7.8 g, 13.2 mmol, yield 72%).

GC-Mass (theory: 593.74 g / mol, measurement: 593 g / mol)

[ Synthetic example  38] Synthesis of 807

5.5 g (17.1 mmol) of A32, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol) g (5 mol%) of Pd (PPh _{3) 4,} and potassium carbonate, 7.0g (51.2 mmol) and 80ml / 40ml / into the toluene / H ₂ O / ethanol of 40ml and the mixture was stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R807 (7.4 g, 12.8 mmol, yield 75%).

GC-Mass (calculated: 578.86 g / mol, measured: 578 g / mol)

[ Example  1 ~ 37] Green organic Field  Fabrication of light emitting device

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

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, 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.

(60 nm) / TCTA (80 nm) / R7, R10, R13, R125, R27, R47, R67, R87, R107, R127, R147, R167, R187, R207, R210, 10% of each compound of R227, R247, R267, R287, R307, R310, R347, R367, R387, R390, R407, R427, R447, R467, R507, R527, R567, R587, R607, R687, R767, Al (200 nm) / Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm).

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP are as follows.

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

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound R7 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  One]

Current efficiency and emission peak at current density (10) mA / cm2 were measured for each of the green organic electroluminescent devices prepared in Examples 1 to 37 and Comparative Example 2. The results are shown in Table 1 below Respectively.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 R7 4.2 515 12.5 Example 2 R10 4.3 515 12.1 Example 3 R13 4.2 515 12.3 Example 4 R125 4.1 515 12.2 Example 5 R27 4.2 515 12.2 Example 6 R47 4.2 515 12.1 Example 7 R67 4.3 515 12.3 Example 8 R87 4.3 515 12.1 Example 9 R107 4.3 515 12.0 Example 10 R127 4.2 515 12.1 Example 11 R147 4.2 515 12.2 Example 12 R167 4.2 515 12.1 Example 13 R187      4.2 515 12.2 Example 14 R207 4.2 515 12.1 Example 15 R210 4.1 515 12.4 Example 16 R227 4.3 515 12.3 Example 17 R247 4.2 515 12.1 Example 18 R267 4.2 515 12.2 Example 19 R287 4.1 515 12.1 Example 20 R307 4.2 515 12.0 Example 21 R310 4.2 515 12.2 Example 22 R347 4.2 515 12.2 Example 23 R367 4.2 515 12.1 Example 24 R387 4.3 515 12.3 Example 25 R390 4.3 515 12.1 Example 26 R407 4.3 515 12.0 Example 27 R427 4.2 515 12.1 Example 28 R447 4.2 515 12.2 Example 29 R467 4.2 515 12.1 Example 30 R487      4.2 515 12.2 Example 31 R507 4.3 515 12.1 Example 32 R527 4.3 515 12.0 Example 33 R567 4.2 515 12.1 Example 34 R587 4.2 515 12.2 Example 35 R607 4.2 515 12.1 Example 36 R687      4.2 515 12.2 Example 37 R767 4.3 515 12.3 Comparative Example 1 CBP 7.1 516 37.1

As shown in Table 1, the compound (R7, R10, R13, R125, R27, R47, R67, R87, R107, R127, R147, R167, R187, R207, R210, R227, R287, R307, R310, R347, R367, R387, R390, R407, R427, R447, R467, R507, R527, R567, R587, R607, R687, R767, R487) were used as a light emitting layer of a green organic electroluminescent device (Examples 1 to 37) Compared with the green organic electroluminescent device using the conventional CBP (Comparative Example 1), it can be seen that the organic electroluminescent device exhibits better performance in terms of efficiency and driving voltage.

[ Example  38 to 48] Blue organic Field  Fabrication of light emitting device

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

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

(DS-205, Doosan Electronics 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / R7, R10, R13, R207 and R287 , Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

Without the use of R7 as the electron transporting the secondary layer material, by and is performed in the same manner as in Example 38 except for depositing the Alq ₃ electron transporting material to 30 nm instead of 25 nm to prepare a blue organic light emitting element.

The structures of NPB, AND and Alq ₃ used in Examples 38 to 48 and Comparative Example 2 are as follows.

[ Comparative Example  3] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 38 except that Al of the following structural formula was used instead of R7 as the electron transporting auxiliary layer material.

[ Evaluation example  2]

The driving voltage, light emission wavelength, and current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 38 to 48 and Comparative Examples 2 to 3, respectively. The results are shown in Table 2 below .

Sample Electron transporting auxiliary layer Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 38 R7 4.0 455 9.8 Example 39 R10 3.9 455 9.2 Example 40 R13 4.1 455 9.4 Example 41 R207 4.2 455 7.8 Example 42 R287 4.2 455 7.8 Example 43 R447 4.0 455 7.5 Example 45 R527 4.2 455 7.4 Example 46 R607 2.5 455 8.2 Example 47 R687 2.8 455 8.3 Example 48 R767 3.5 455 7.2 Comparative Example 2 Alq ₃ 4.8 458 6.2 Comparative Example 3 A1 4.7 457 6.5

As shown in Table 2, the blue organic electroluminescent devices (Examples 38 to 48) using the compound of the present invention as the electron transporting auxiliary layer (Examples 38 to 48) contained blue organic electroluminescent devices (Comparative Examples 2 and 3) Emitting peak, and driving voltage, as compared with that of the conventional organic EL device.

[ Example  49 to 59] Blue organic Field  Fabrication of light emitting device

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

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

NPN (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / R10, R13, R207, R287, (30 nm) / LiF (1 nm) / Al (200 nm) in the order of compounds R447, R527, R607, R687, R767 and R807 were stacked in this order to fabricate an organic electroluminescent device.

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

A blue organic electroluminescent device was fabricated in the same manner as in Example 49 except that Alq ₃ was used instead of R7 as the electron transport layer material.

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

A blue organic electroluminescent device was fabricated in the same manner as in Example 49 except that R7 was not used as the electron transport layer material.

[ Evaluation example  3]

The driving voltage, current efficiency and emission wavelength at the current density of 10 mA / cm 2 were measured for the blue organic electroluminescent devices fabricated in Examples 49 to 59 and Comparative Examples 2 and 3, Respectively.

Sample Electron transport layer Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 49 R7 4.1 455 8.7 Example 50 R10 4.2 455 8.1 Example 51 R13 4.0 455 8.1 Example 52 R207 4.1 455 8.2 Example 53 R287 4.2 455 8.3 Example 54 R447 4.0 455 7.8 Example 55 R527 4.0 455 8.1 Example 56 R607 3.1 455 7.9 Example 57 R687     2.8 455 7.5 Example 58 R767 3.9 455 7.0 Example 59 R807 3.5 455 6.5 Comparative Example 4 Alq ₃ 4.7 458 5.5 Comparative Example 5 - 4.8 460 6.2

As shown in Table 3, the blue organic electroluminescent devices (Examples 49 to 59) using the compound of the present invention as the electron transport layer (Comparative Examples 4 and 5) used conventional Alq ₃ as the electron transport layer and the blue organic electroluminescent devices Emitting layer exhibited excellent performance in terms of driving voltage, luminescent peak and current efficiency as compared with the blue organic electroluminescent device without the electron transport layer (Comparative Example 5).

10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transporting auxiliary layer
34: Electron transport layer 35: Electron transport layer
36: electron injection layer 37: hole injection layer

Claims (17)

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

In Formula 1,
X ₁ is selected from the group consisting of S, O, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ );
X ₂ and X ₃ are each independently N or C (Ar ₄ );
Ring A is represented by any one of the following formulas (2) to (4);
(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,
The dotted line means the part where the condensation is made;
m is an integer from 0 to 4;
n is an integer from 0 to 6;
Ar ₁ to Ar ₄ and R ₁ are each independently a substituent represented by the following formula (5), and when a plurality of R _{1 s} are present, they are the same or different;
[Chemical Formula 5]

In Formula 5,
* Denotes the part where the bond is made;
L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
R ₂ is 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 cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;
Wherein L ₁ and the L ₂ arylene group and a heteroarylene group, an alkyl group of the R _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, 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 alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein said compound is represented by any one of the following formulas (6) to (11):
[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above formulas 6 to 11,
Ring A and Ar &_lt; ₁ > to Ar &_lt; ₄ > are as defined in claim 1. 3. The method of claim 2,
Wherein said compound is represented by any one of formulas (6) and (8) to (11). The method according to claim 1,
Each of Ar ₁ to Ar ₄ is independently a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms,
The aryl group and the heteroaryl group of Ar ₁ to Ar ₄ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ arylamine group, a C ₆ to C ₆₀ aryl group, A heteroaryl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other. 5. The method of claim 4,
Ar ₁ to Ar ₄ each independently represent a phenyl group, a biphenyl group, a naphthalenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, A fluorenyl group, and a dibenzodioxinyl group,
The aryl group of Ar ₁ to Ar ₄ is preferably a phenyl group, a biphenyl group, a naphthalenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group And dibenzodioxinyl groups are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, naphthalenyl, pyridinyl, pyrimidinyl, Benzothiophenyl group, carbazolyl group, fluorenyl group, spirofluorenyl group and dibenzodioxinyl group, and when they are substituted with a plurality of substituents, they may be the same or different from each other Lt; / RTI > The method according to claim 1,
Wherein L ₁ and L ₂ are each independently a direct bond or a linker represented by any one of the following formulas A-1 to A-6:

In the above Formulas A-1 to A-6,
* Denotes the part where the bond is made;
Z ₁ to Z ₈ are each independently N or C (Ar ₅ );
Any two of Z ₁ to Z ₆ bonded as a linker in the above formula (A-1) are C (Ar ₅ ), wherein Ar ₅ is a member;
Any one of Z ₁ to Z ₄ and any of Z ₅ to Z ₈ which is bonded as a linker in the above formula (A-3) is C (Ar ₅ ), wherein Ar ₅ is a member;
Any two of Z ₁ to Z ₄ bonded as a linker in the above formula (A-4) are C (Ar ₅ ), wherein Ar ₅ is a member;
X ₅ and X ₆ are each independently O, S, N (Ar ₆ ) or C (Ar ₇ ) (Ar ₈ );
X ₇ is N or C (Ar ₉ );
Ar ₅ to Ar ₉ 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, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a group that is selected or adjacent from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ bond to form a condensed ring, and said Ar ₅ To Ar ₈ are plural, they are the same or different from each other;
Alkyl groups of the Ar ₅ to Ar _9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein L ₁ and L ₂ are each independently a direct bond or a linker represented by any one of the following formulas B-1 to B-11:

In the above Formulas B-1 to B-11,
* Denotes the part where the bond is made;
Ar ₆ to Ar ₉ 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, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
Alkyl groups of the Ar ₆ to Ar _9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl And when they are substituted with a plurality of substituents, they are the same as or different from each other. 8. The method of claim 7,
Wherein L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of Formulas B-1, B-2 and B-6 to B-11. The method according to claim 1,
Wherein R < ₂ > is a substituent represented by the following formula (12):
[Chemical Formula 12]

In Formula 12,
* Denotes the part where the bond is made;
Y ₁ to Y ₅ are each independently N or C (Ar ₁₀ );
Ar ₁₀ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of is selected from the group consisting of aryl amine group, when the Ar ₁₀ are the same or different, and plural individual these;
Alkyl groups of the Ar _10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _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 C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphazene group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the Is optionally substituted on a substituent group, if substituted to a plurality of substituents, they are same as or different from each other. 10. The method of claim 9,
Wherein the substituent represented by the formula (12) is a substituent represented by the following formula (13):
[Chemical Formula 13]

In Formula 13,
* Denotes the part where the bond is made;
R ₃ and R ₄ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
Alkyl group of the R ₃ and R _4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with a plurality of substituents, they are the same as or different from each other;
Each of Z ₁ , Z ₃ and Z ₅ is as defined in claim 9. 10. The method of claim 9,
Wherein the substituent represented by the formula (12) is a substituent represented by any one of the following formulas (B-1) to (B-3):

In the above formulas C-1 to C-5,
* Denotes the part where the bond is made,
R ₃ and R ₄ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
Alkyl group of the R ₃ and R _4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 And when they are substituted with a plurality of substituents, they are the same as or different from each other. 11. The method of claim 10,
Each of R ₃ and R ₄ is independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,
The alkyl, aryl and heteroaryl groups of R ₃ and R ₄ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein R < ₂ > is a substituent represented by the following formula (14):
[Chemical Formula 14]

In Formula 14,
* Denotes the part where the bond is made;
R ₅ and R ₆ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 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 aryl phosphazene group, selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring;
Alkyl groups of the R ₅ and R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 And when they are substituted with a plurality of substituents, they are the same as or different from each other. 14. The method of claim 13,
Each of R ₅ and R ₆ is independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,
The alkyl, aryl and heteroaryl groups of R ₅ and R ₆ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein said compound is selected from the group consisting of:

1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound represented by the general formula (1). 17. The method of claim 16,
Wherein the organic material layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transporting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and a light emitting layer.

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