WO2018093107A1 - Organic compound and organic electroluminescent element comprising same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent element comprising the same. The compound according to the present invention is used in an organic compound layer of an organic electroluminescent element, preferably in a light-emitting layer, an electron transfer layer, or an electron transport auxiliary layer. Accordingly, the luminous efficiency, the driving voltage, the life span, etc. of the organic electroluminescent element can be improved.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

From the observation of Bernanose organic thin film emission in the 1950s, the study of organic electroluminescent (EL) devices led to blue electroluminescence using anthracene single crystal in 1965, followed by Tang in 1987 The organic electroluminescent device of the laminated structure divided into the functional layer of a positive hole layer and a light emitting layer was proposed. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.

The dopant material may 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 compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

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

However, the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.

The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent holes, electron injection and transport ability, light emitting ability and the like.

Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage and high luminous efficiency and has an improved lifetime.

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

[Formula 1]

In Chemical 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 one of formulas 2 to 4;

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 1 to 4,

The dotted line means the part where condensation takes place;

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 Formula 5, and when there are a plurality of R ₁ , they are the same as or different from each other;

 [Formula 5]

In Chemical Formula 5,

* Means the part where the bond is made;

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

R ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha A silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

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 The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently 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 nuclear atom having 5 to 60 heteroaryl groups, a C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When unsubstituted or substituted with one or more substituents selected from the group consisting of arylsilyl groups, they are the same as or different from each other.

The present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .

"Alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.

"Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.

"Alkynyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom (for example, may have 8 to 60 carbon atoms), and the whole molecule has non-aromacity 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. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1-40 alkyl, and is linear, branched or cyclic structure. Interpret as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

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

By "cycloalkyl" in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

“Heterocycloalkyl” in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.

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

Since the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL 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 since the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.

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

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

10: anode 20: cathode

30: organic layer 31: hole transport layer

32: light emitting layer 33: hole transport auxiliary layer

34: electron transport layer 35: electron transport auxiliary layer

36: electron injection layer 37: hole injection layer

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

[Formula 1]

In Chemical 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 one of formulas 2 to 4;

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 1 to 4,

The dotted line means the part where condensation takes place;

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 Formula 5, and when there are a plurality of R ₁ , they are the same as or different from each other;

 [Formula 5]

In Chemical Formula 5,

* Means the part where the bond is made;

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

R ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha A silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

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 The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently 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 nuclear atom having 5 to 60 heteroaryl groups, a C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When unsubstituted or substituted with one or more substituents selected from the group consisting of arylsilyl groups, they are the same as or different from each other.

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 (1):

[Formula 1]

In Chemical 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 one of formulas 2 to 4;

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 1 to 4,

The dotted line means the part where condensation takes place;

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 Formula 5, and when there are a plurality of R ₁ , they are the same as or different from each other;

 [Formula 5]

In Chemical Formula 5,

* Means the part where the bond is made;

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

R ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha A silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

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 The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently 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 nuclear atom having 5 to 60 heteroaryl groups, a C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When unsubstituted or substituted with one or more substituents selected from the group consisting of arylsilyl groups, they are the same as or different from each other.

However, in the present invention, in the case where R ₁ is represented by the formula (5), L ₁ and L ₂ are at the same time a direct bond and R ₂ is except for hydrogen.

The organic compound of the present invention is a compound having a structure in which one or more substituents connected directly to or connected to a moiety having a 5-membered aromatic ring or a 5-membered aromatic hetero ring are linked through a linker group. Can be displayed.

In the present invention, the 5-membered aromatic ring or 5-membered aromatic hetero ring may be an indole moiety, an indazole moiety, an indene moiety, a benjofuran moiety, a benjoiophene, a triazolo, etc., but is not limited thereto.

More specifically, the compound represented by Formula 1 of the present invention is that EWG is bonded to a 5-membered aromatic ring or 5-membered aromatic hetero, such as indole, indazole indene, benjofuran, benzothiophene, triazolo, etc. Since it has an energy level similar to that of sol, it can be adjusted higher than the energy level of the dopant, and thus can be applied as a host material. In particular, the moieties of benjofuran and benzojofen are rich in electrons, and therefore, mobility can be increased when used as an electron transport layer material of an organic electroluminescent device, so that the luminous efficiency can be increased and the driving voltage can be expected to decrease. In addition, since the 5-membered aromatic ring or 5-membered aromatic hetero ring of the present invention has a lower molecular weight than conventional compounds, it is possible to deposit at a lower temperature than other materials at the time of deposition, thereby improving processability and thermal stability. Can be.

Accordingly, the compound represented by Formula 1 of the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (green phosphorescent host material), an electron transport layer / injection layer material light emitting auxiliary layer material, life improvement layer material, more Preferably it can be used as a light emitting layer material, an electron injection layer material, an electron transporting layer material. In addition, the organic electroluminescent device including the compound of Formula 1 may significantly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.

According to one preferred embodiment of the invention, the compound may be represented by any one of the following formulas 6 to 11.

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

In Chemical Formulas 6 to 11,

Ring A and Ar ₁ to Ar ₄ are each as defined in Chemical Formula 1.

According to a preferred embodiment of the present invention, the compound is preferably represented by any one of the formulas (6) and (8) to (11) to secure a low driving voltage and high luminous efficiency, more preferably to any one of the formulas (8) to (10) It may be represented, more preferably may be represented by the formula (8) or (10).

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

The aryl group and heteroaryl group of Ar ₁ to Ar ₄ are each independently C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ aryl group and 5 to 60 nuclear atoms When substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups, and substituted with a plurality of substituents, they may be the same or different from each other.

According to one preferred embodiment of the present invention, Ar ₁ to Ar ₄ are each independently a phenyl group, a biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group , Carbazolyl group, fluorenyl group, spirofluorenyl group and dibenzodioxyyl group,

The phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorenyl group and spirofluorenyl group of Ar ₁ to Ar ₄ and dibenzo-deoxy carbonyl groups are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl amine group, C ₆ ~ C ₆₀ aryl group and the number of nuclear atoms of 5 to 60 hetero aryl group from the group consisting of When substituted or unsubstituted with one or more selected substituents, and substituted with a plurality of substituents, they may be the same or different from each other.

According to one preferred embodiment of the present invention, Ar ₁ to Ar ₄ are each independently a phenyl group, a biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group , Carbazolyl group, fluorenyl group, spirofluorenyl group and dibenzodioxyyl group,

The phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorenyl group and spirofluorenyl group of Ar ₁ to Ar ₄ And dibenzodioxynyl groups are each independently methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, naphthalenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, and di When substituted or unsubstituted with one or more substituents selected from the group consisting of a benzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxyyl group, and substituted with a plurality of substituents, Can be different.

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

In Chemical Formulas A-1 to A-6,

* Means 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 which are bonded as a linker in Formula A-1 is C (Ar ₅ ), wherein Ar ₅ is absent;

Any one of Z ₁ to Z ₄ and Z ₅ to Z ₈ which are bonded as a linker in Formula A-3 is C (Ar ₅ ), wherein Ar ₅ is absent;

Any one of Z ₁ to Z ₄ which is bonded as a linker in Formula A-4 is C (Ar ₅ ), wherein Ar ₅ is absent;

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 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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 Or when Ar ₈ is a plurality, they are the same as or different from each other;

An alkyl group, 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 of Ar ₅ to Ar ₉ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 Aryl boron group of ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When unsubstituted or substituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other.

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

In Chemical Formulas B-1 to B-11,

* Means the part where the bond is made;

Ar ₆ to Ar ₉ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of Ar ₆ to Ar ₉ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 Aryl boron group of ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When unsubstituted or substituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other.

According to one preferred embodiment of the present invention, in Formulas B-1 to B-11, Ar ₆ to Ar ₉ are each independently hydrogen, an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ and 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 C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ When substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and substituted with a plurality of substituents, they are the same or different from each other.

According to one preferred embodiment of the present invention, L ₁ and L ₂ may be 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 one preferred embodiment of the present invention, R ₂ may be a substituent represented by Formula 12:

[Formula 12]

In Chemical Formula 12,

* Means the part where the bond is made;

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

Ar ₁₀ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha A silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group, and when there are a plurality of Ar ₁₀ , they are the same or different from each other;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of Ar ₁₀ , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ 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 Formula 12 may be a substituent represented by the following formula (13):

[Formula 13]

In Chemical Formula 13,

* Means the part where the bond is made;

R ₃ and R ₄ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₃ and R ₄ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other;

Y ₁ , Y ₃ and Y ₅ are each as defined in Chemical Formula 12.

According to a preferred embodiment of the present invention, the substituent represented by Formula 12 may be a substituent represented by any one of the following formulas C-1 to C-5:

In Chemical Formulas C-1 to C-5,

* Means the part where the coupling is made,

R ₃ and R ₄ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₃ and R ₄ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.

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

The alkyl group, aryl group and heteroaryl group of R ₃ and R ₄ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and 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 a phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group Is selected from the group consisting of

Of 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 -C ₄₀ alkyl group, a C ₆ -C ₆₀ aryl group And it is unsubstituted or substituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₃ and R ₄ are each independently a phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group Is selected from the group consisting of

Of 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 methyl group, an ethyl group, a propanyl group, a butyl group, a phenyl group, a biphenyl group, When substituted or unsubstituted 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, they are substituted with a plurality of substituents. They are the same or different from each other.

According to one preferred embodiment of the present invention, R ₂ may be a substituent represented by Formula 14:

[Formula 14]

In Chemical Formula 14,

* Means the part where the bond is made;

R ₅ and R ₆ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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 group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₅ and R ₆ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 or unsubstituted with at least one substituent, and 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 group consisting of an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C _{60 and} a heteroaryl group of 5 to 60 nuclear atoms Selected,

The alkyl group, aryl group and heteroaryl group of R ₅ and R ₆ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and 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, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group Is selected from the group consisting of

Of 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 -C ₄₀ alkyl group, a C ₆ -C ₆₀ aryl group And it is unsubstituted or substituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups, they are the same 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, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group Is selected from the group consisting of

Of 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 methyl group, an ethyl group, a propanyl group, a butyl group, a phenyl group, a biphenyl group, When substituted or unsubstituted 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, they are substituted with a plurality of substituents. They are the same or different from each other.

Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

2. Organic Electric field  Light emitting element

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound may be used alone or mixed two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.

The structure of the organic EL device according to the present invention described above is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them. The organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32, and an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.

Referring to FIG. 2 as another example of the present invention, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode The electron injection layer 36 may be further included between the holes 20.

In the present invention, the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 may not only improve the interface property between the ITO used as the anode and the organic material used as the hole transport layer 31. However, the surface is applied to the upper surface of the uneven ITO to soften the surface of the ITO, a layer that can be used without particular limitation as long as it is commonly used in the art, for example, may be used an amine compound It is not limited to this.

In addition, the electron injection layer 36 is stacked on top of the electron transport layer to facilitate the injection of electrons from the cathode to perform a function that ultimately improves the power efficiency, which is specially used in the art It can be used without limitation, and materials such as LiF, Liq, NaCl, CsF, Li ₂ O, BaO and the like can be used.

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

In addition, although not shown in the drawings in the present invention, a life improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes traveling through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer, and thus do not diffuse or move to the electron transport layer, and consequently, the holes are limited to the light emitting layer. . Such a function of limiting holes to the light emitting layer prevents holes from diffusing into the electron transporting layer that moves electrons by reduction, thereby suppressing the lifespan phenomenon through irreversible decomposition reaction by oxidation and contributing to improving the life of the organic light emitting device. Can be.

In the present invention, the compound represented by Chemical Formula 1 is that EWG is bonded to a 5-membered aromatic ring or 5-membered aromatic hetero, such as indole, indazole indene, benjofuran, benzothiophene, triazolo, etc. Since the energy level is higher than the energy level of the dopant, it can be applied as a host material. In particular, the moieties of benzofuran and benzothiophene are rich in electrons, and thus, when used as an electron transporting layer material of an organic electroluminescent device, the mobility of the benzofuran and the benzothiophene can be expected to be increased and the driving voltage can be increased. In addition, since the 5-membered aromatic ring or 5-membered aromatic hetero ring of the present invention has a lower molecular weight than conventional compounds, it is possible to deposit at a lower temperature than other materials at the time of deposition, thereby improving processability and thermal stability. Can be.

Therefore, the compound represented by Chemical Formula 1 of the present invention may be used as any one of a material of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic material layers of an organic electroluminescent device. It can be used as a material of any one of the transport layer and the electron transport auxiliary layer further laminated on the electron transport layer, more preferably the electron transport layer, or the material of the electron transport auxiliary layer.

In addition, when the compound according to the present invention is used as a light emitting layer material, specifically, the compound represented by Formula 1 may be used as a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, preferably a phosphorescent host (blue, green). And / or red phosphorescent host materials).

In addition, in the present invention, the organic electroluminescent device may not only sequentially stack an anode, at least one organic material layer, and a cathode as described above, but may further include an insulating layer or an adhesive layer at an interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (for example, an electron transport auxiliary layer) is formed to include the compound represented by Chemical Formula 1. It can be prepared by forming other organic material layer and electrode using.

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 silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

Further, the positive electrode material may be made of a high work function conductor, for example, to facilitate hole injection, and may include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : 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.

In addition, the cathode material may be made of a low work function conductor, for example, to facilitate electron injection, and may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

[ Preparation  1] Synthesis of A1

6.7 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 1- (3-bromophenyl) -1H-indazole under nitrogen stream 7.4 g (29.2 mmol) of '-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) of KOAc and 1,4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After the completion of the reaction, the mixture was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A1, (5.5g, 17.1 mmol, 70% yield).

GC-Mass (Theoretical value: 320.19 g / mol, Measured value: 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  2] Synthesis of A2

8.5 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 1- (3-bromophenyl) -3-phenyl-1H-indazole under nitrogen stream 7.4 g (29.2 mmol), Pd (dppf) Cl ₂ 0.6 g (0.7 mmol), KOAc 7.2 g (73.1 mmol), and 1,2,2'-ratio (1,3,2-dioxaborolane) 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After the completion of the reaction, the mixture was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A2, (6.8g, 17.1mmol, yield 70%).

GC-Mass (Theoretical value: 369.29 g / mol, Measured value: 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  3] Synthesis of A3

8.5 g (24.4 mmol) of 1- (3-bromophenyl) -3- (pyridin-4-yl) -1H-indazole, 4,4,4 ', 4', 5,5,5 'under nitrogen stream , 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 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 ° C. for 6 hours.

After the completion of the reaction, the mixture was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A3, (7.3g, 18.3 mmol, yield 75%).

GC-Mass (Theoretical value: 397.28 g / mol, Measured value: 397 g / mol)

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

[ Preparation  4] Synthesis of A4

8.5 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 1- (3-bromophenyl) -5-phenyl-1H-indazole under nitrogen stream 7.4 g (29.2 mol) -2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc, and 1, 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After the completion of the reaction, the mixture was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A4, (7.2 g, 18.3 mmol, yield 75%).

GC-Mass (Theoretical value: 396.29 g / mol, Measured value: 396 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 7.43 ~ 7.59 (m, 7H), 7.62 ~ 7.74 (m, 3H), 7.92 (d, 1H), 8.17 (d, 1H), 8.35 (s, 1H )

[ Preparation  5] Synthesis of A5

8.5 g (24.4 mmol) of 1- (3-bromophenyl) -5- (pyridin-4-yl) -1H-indazole, 4,4,4 ', 4', 5,5,5 'under nitrogen stream , 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 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 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A5, (7.5g, 19.0 mmol, yield 78%).

GC-Mass (Theoretical value: 397.28 g / mol, Measured value: 397 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 7.43 ~ 7.59 (m, 4H), 7.62 ~ 7.74 (m, 3H), 7.92 (d, 1H), 8.17 (d, 1H), 8.35 (s, 1H ), 8,71-8.72 (m, 2H)

[ Preparation  6] Synthesis of A6

10.4 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5' 1- (3-bromophenyl) -3,5-diphenyl-1H-indazole under nitrogen stream -Octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 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 ° C. for 6 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A6, (9.0g, 19.0 mmol, yield 78%).

GC-Mass (Theoretical value: 472.39 g / mol, Measured value: 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  7] Synthesis of A7

8.5 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 5- (3-bromophenyl) -1-phenyl-1H-indazole under nitrogen stream 7.4 g (29.2 mol), -2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) of KOAc, and 1, 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A7, (6.3g, 18.0 mmol, 74% yield).

GC-Mass (Theoretical value: 369.29 g / mol, Measured value: 369 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 7.45 (s, 1H), 7.47 ~ 7.62 (m, 9H), 8.01 (s, 1H), 8.17 (d, 1H), 8.32 (s, 1H)

[ Preparation  8] Synthesis of A8

10.4 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5', 5- (3-bromophenyl) -1,3-diphenyl-1H-indazole under nitrogen stream -Octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 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 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 472.39 g / mol, Measured value: 472 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 7.45 (s, 1H), 7.47 ~ 7.62 (m, 12H), 7.88 ~ 7.89 (m, 2H), 8.01 (s, 1H), 8.17 (d, 1H )

[ Preparation  9] Synthesis of A9

8.5 g (24.4 mmol), 4,4,4 ', 4', 5,5,5'5- (3-bromophenyl) -1- (pyridin-4-yl) -1H-indazole under nitrogen stream , 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 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 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A9, (6.8 g, 18.0 mmol, yield 74%).

GC-Mass (Theoretical value: 397.28 g / mol, Measured value: 397 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 7.45 (s, 1H), 7.47 ~ 7.62 (m, 6H), 8.01 (s, 1H), 8.17 (d, 1H), 8.32 (s, 1H), 8.45-8.46 (m, 2H)

[ Preparation  10] Synthesis of A10

17.9 g (24.4 mmol) of 12-bromo-7-phenylanthra [2,3-b] benzo [d] furan under nitrogen stream, 4,4,4 ', 4', 5,5,5 ', 5'-Octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 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 ° C. for 6 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate and then water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A10, (14.1g, 18.0 mmol, yield 74%).

GC-Mass (Theoretical value: 779.73 g / mol, Measured value: 779 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 7.45 (s, 1H), 7.47 ~ 7.58 (m, 14H), 7.62 ~ 7.70 (m, 4H), 7.72 (s, 1H), 8.01 (s, 1H ), 8.08 (s, 1H), 8.17 (d, 1H), 8.24-8.30 (m, 6H), 8.32 (s, 1H)

[ Preparation  11] Synthesis of A11

7.9 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 3- (3-bromophenyl) -3H-benzo [e] indazole under nitrogen stream 7.4 g (29.2 mol) -2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc, and 1, 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After the completion of the reaction, the mixture was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A11, (6.3 g, 17.1 mmol, 70% yield).

GC-Mass (Theoretical value: 370.25 g / mol, Measured value: 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  12] Synthesis of A12

9.7 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5 3- (3-bromophenyl) -1-phenyl-3H-benzo [e] indazole under nitrogen stream 7.4 g (29.2 mol) '-octamethyl-2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A12, (7.6g, 17.1 mmol, yield 70%).

GC-Mass (Theoretical value: 446.35 g / mol, Measured value: 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  13] Synthesis of A13

9.7 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5 8- (3-bromophenyl) -3-phenyl-3H-benzo [e] indazole under nitrogen stream 7.4 g (29.2 mol) '-octamethyl-2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) of KOAc ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 446.35 g / mol, Measured value: 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  14] Synthesis of A14

11.6 g (24.4 mmol), 4,4,4 ', 4 3- (3-bromophenyl) -1-phenyl-8- (pyridin-4-yl) -3H-benzo [e] indazole under nitrogen stream ', 5,5,5', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 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 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 523.43 g / mol, Measured value: 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 to 8.56 (m, 2H)

[ Preparation  15] Synthesis of A15

19.1 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5 3- (3-bromophenyl) -1-phenyl-3H-benzo [e] indazole under nitrogen stream 7.4 g (29.2 mol) '-octamethyl-2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 829.79 g / mol, Measured value: 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), 7.78 ~ 7.92 (m, 3H), 8.08 (s, 1H), 8.18 ~ 8.35 (m, 7H), 8.35 (s, 1H)

[ Preparation  16] Synthesis of A16

7.9 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 1- (3-bromophenyl) -1H-benzo [f] indazole under nitrogen stream 7.4 g (29.2 mol) -2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc, and 1, 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A16, (6.3g, 17.1 mmol, yield 70%).

GC-Mass (Theoretical value: 370.25 g / mol, Measured value: 370 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 7.44 (s, 1H), 7.45 ~ 7.61 (m, 4H), 7.65 (s, 1H), 7.72 (s, 1H), 7.75 (d, 1H), 8.18-8.19 (m, 2H), 8.35 (s, 1H)

[ Preparation  17] Synthesis of A17

9.7 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5 6- (3-bromophenyl) -1-phenyl-1H-benzo [f] indazole under nitrogen stream 7.4 g (29.2 mol) '-octamethyl-2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A17, (7.6g, 17.1 mmol, yield 70%).

GC-Mass (Theoretical value: 446.35 g / mol, Measured value: 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), 7.72 (s, 1H), 7.75 (d, 1H), 8.18 ~ 8.19 (m, 2H), 8.35 (s, 1H)

[ Preparation  18] Synthesis of A18

19.1 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5 3- (3-bromophenyl) -1-phenyl-3H-benzo [e] indazole under nitrogen stream 7.4 g (29.2 mol) '-octamethyl-2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A18, (15.8g, 19.0 mmol, yield 78%).

GC-Mass (Theoretical value: 829.79 g / mol, Measured value: 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), 7.72 (s, 1H), 7.73 (s, 1H), 7.74 (s, 1H), 7.75 (d, 1H), 8.10 (s, 1H), 8.15 ~ 8.19 (m, 7H), 8.35 (s, 1H)

[ Preparation  19] Synthesis of A19

7.9 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 1- (3-bromophenyl) -1H-benzo [g] indazole under nitrogen stream 7.4 g (29.2 mol) -2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc, and 1, 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A19, (6.3g, 17.1 mmol, yield 70%).

GC-Mass (Theoretical value: 370.25 g / mol, Measured value: 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, 1H) , 8.16 (d, 1 H), 8.35 (s, 1 H), 8.55 (d, 1 H),

[ Preparation  20] Synthesis of A20

9.7 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5 7- (3-bromophenyl) -1-phenyl-1H-benzo [g] indazole under nitrogen stream 7.4 g (29.2 mol) '-octamethyl-2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A20, (7.6g, 17.1 mmol, yield 70%).

GC-Mass (Theoretical value: 446.35 g / mol, Measured value: 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  21] Synthesis of A21

19.1 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5 3- (3-bromophenyl) -1-phenyl-3H-benzo [e] indazole under nitrogen stream 7.4 g (29.2 mol) '-octamethyl-2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc ) And 1,4-dioxane (200 ml) were mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate and then water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A21, (15.8g, 19.0 mmol, yield 78%).

GC-Mass (Theoretical value: 829.79 g / mol, Measured value: 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), 7.69 (s, 1H), 7.70 (s, 1H), 7.71 (d, 1H), 7,91 (d, 1H), 8.10 (s, 1H), 8.15-8.23 (m, 5H), 8.35 (s, 1H)

[ Preparation  22] Synthesis of A22

6.6 g (24.4 mmol) of 1- (3-bromophenyl) -1H-indazole, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 under nitrogen stream '-Ratio (1,3,2-dioxaborolane) 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) was mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 319.21 g / mol, Measured value: 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  23] Synthesis of A23

8.5 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 1- (3-bromophenyl) -3-phenyl-1H-indazole under nitrogen stream 7.4 g (29.2 mol) -2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc, and 1, 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 395.30 g / mol, Measured value: 395 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 7.32 (s, 1H), 7.42 (s, 1H), 7.46 ~ 7.65 (m, 11H), 8.15 (d, 1H)

[ Preparation  24] Synthesis of A24

8.5 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 1- (3-bromophenyl) -5-phenyl-1H-indazole under nitrogen stream 7.4 g (29.2 mol) -2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc, and 1, 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 395.30 g / mol, Measured value: 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, 1H), 8.08 ~ 8.15 (m, 2H)

[ Preparation  25] Synthesis of A24

Y1 17.9 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-ratio (1,3,2-dioxabolic) under nitrogen stream Lorane) 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 for 6 hours at 130 ° C. Stirred.

After completion of the reaction, the mixture was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A25, (14.2g, 18.3 mmol, yield 75%).

GC-Mass (Theoretical value: 778.75 g / mol, Measured value: 778 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 6.51 (d, 1H), 7.44 ~ 7.61 (m, 18H), 7.65 (s, 1H), 7.69 (s, 1H), 7,71 (s, 1H ), 7.76 (s, 1 H), 8.08 (s, 1 H), 8.12-8.25 (m, 7H)

[ Preparation  26] Synthesis of A26

7.8 g (24.4 mmol) of 1- (3-bromophenyl) -1H-indazole under nitrogen stream, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 '-Ratio (1,3,2-dioxaborolane) 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) was mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 369.26 g / mol, Measured value: 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  27] Synthesis of A27

7.9 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl 1- (3-bromophenyl) -3-phenyl-1H-indazole under nitrogen stream 7.4 g (29.2 mol) -2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc, and 1, 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 369.26 g / mol, Measured value: 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), 7.59 (s, 1H), 7.69 ~ 7.79 (m, 3H ), 8.08-8.10 (d, 2H)

[ Preparation  28] Synthesis of A28

7.9 g (24.4 mmol) of 1- (3-bromophenyl) -1H-indazole, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 under nitrogen stream '-Ratio (1,3,2-dioxaborolane) 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) was mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 369.26 g / mol, Measured value: 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  29] Synthesis of A29

6.7 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-ratio of 5- (3-bromophenyl) benzofuran under nitrogen stream (1,3,2-dioxaborolane) 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 ) Was mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 369.26 g / mol, Measured value: 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  30] Synthesis of A30

7.3 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octa, 5- (3-bromophenyl) -1,1-dimethyl-1H-indene under nitrogen stream 7.4 g (29.2 mol) methyl-2,2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) KOAc, and 1 , 4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the title compound A30, (5.9g, 17.1 mmol, yield 70%).

GC-Mass (Theoretical value: 346.27 g / mol, Measured value: 346 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 1.69 (s, 6H), 6.65 (d, 1H), 7.55 ~ 7.59 (m, 3H), 7.62 (s, 1H), 7.75 (s, 1H), 7.72-7.79 (m, 3H)

[ Preparation  31] Synthesis of A31

7.0 g (24.4 mmol) of 5- (3-bromophenyl) benzo [b] thiophene, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2, 7.4 g (29.2 mol) 2'-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) of KOAc and 1,4-di Oxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

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

GC-Mass (Theoretical value: 336.26 g / mol, Measured value: 326 g / mol)

¹ H-NMR: δ 1.25 (s, 12H), 6.65 (d, 1H), 7.55 ~ 7.59 (m, 3H), 7.69 (s, 1H), 7.75 ~ 7.79 (m, 3H), 7.95 (s, 1H )

[ Preparation  32] Synthesis of A32

6.7 g (24.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 1- (3-bromophenyl) -1H-indazole under nitrogen stream 7.4 g (29.2 mmol) of '-ratio (1,3,2-dioxaborolane), 0.6 g (0.7 mmol) of Pd (dppf) Cl ₂ , 7.2 g (73.1 mmol) of KOAc and 1,4-dioxane (200 ml) was mixed and stirred at 130 ° C. for 6 hours.

After completion of the reaction, the resultant was extracted with ethyl acetate, water was removed with MgSO ₄ and purified by column chromatography to obtain the target compound A32, (5.5g, 17.1 mmol, yield 70%).

GC-Mass (Theoretical value: 321.18 g / mol, Measured value: 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)

[ Synthesis Example  1] Synthesis of R7

5.5 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R7, (7.4g, 12.8 mmol, yield 75%).

GC-Mass (Theoretical value: 577.68 g / mol, Measured value: 577 g / mol)

[ Synthesis Example  2] Synthesis of R10

5.5 g (17.1 mmol) A1, 2-bromo-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine, 9.2 g (18.8 mmol) under nitrogen stream ), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 ° C. for 3 hours. It was.

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 was purified by column chromatography to give the title compound R10, (7.7g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 605.64 g / mol, Measured value: 605 g / mol)

[ Synthesis Example  3] Synthesis of R13

5.5 g (17.1 mmol), 2- (7- (3-bromophenyl) -9,9-dimethyl-9H-fluoren-2-yl) -4,6-diphenyl-1,3 under nitrogen stream , 5-triazine, 10.9 g (18.8 mmol), 1.0 g (5 mol%) of 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 was added and 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 was purified by column chromatography to give the title compound R13, (7.6g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 617.74g / mol, Measured value: 617g / mol)

[ Synthesis Example  4] Synthesis of R25

6.8 g (17.1 mmol) A2, 4- (biphenyl-4-yl) -6-bromo-2-phenylpyrimidine, 7.3 g (18.8 mmol), 1.0 g (5 mol%) of Pd under nitrogen stream 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 were added thereto and 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 was purified by column chromatography to give the title compound R25, (7.4g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 576.69g / mol, Measured value: 576g / mol)

[ Synthesis Example  5] Synthesis of R127

6.8 g (17.1 mmol) A2, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R27, (8.4g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 653.77g / mol, Measured value: 653g / mol)

[ Synthesis Example  6] Synthesis of R47

7.3 g (18.3 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.3 g (20.1 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.6 g (54.8 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol 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 was purified by column chromatography to give the title compound R47, (9.0g, 13.7 mmol, yield 75%).

GC-Mass (Theoretical value: 654.76g / mol, Measured value: 654g / mol)

[ Synthesis Example  7] Synthesis of R67

7.2 g (18.3 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.3 g (20.1 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.6 g (54.8 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol 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 was purified by column chromatography to give the title compound R67, (9.0g, 13.7 mmol, 75% yield).

GC-Mass (Theoretical value: 653.77g / mol, Measured value: 653g / mol)

[ Synthesis Example  8] Synthesis of R87

7.6 g (19.0 mmol) A2, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol), 1.1 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.9 g (57.0 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R87, (9.3g, 14.3 mmol, 75% yield).

GC-Mass (Theoretical value: 654.76g / mol, Measured value: 654g / mol)

[ Synthesis Example  9] Synthesis of R107

9.0 g (19.0 mmol) of A6, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol), 1.1 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.9 g (57.0 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R107, (10.4g, 14.3 mmol, 75% yield).

GC-Mass (Theoretical value: 729.87g / mol, Measured value: 729g / mol)

[ Synthesis Example  10] Synthesis of R127

6.3 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R127, (8.4g, 12.8 mmol, yield 75%).

GC-Mass (Theoretical value: 653.77g / mol, Measured value: 653g / mol)

[ Synthesis Example  11] Synthesis of R147

8.1 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R147, (8.4g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 654.76g / mol, Measured value: 654g / mol)

[ Synthesis Example  12] Synthesis of R167

6.8 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R167, (9.3g, 12.4 mmol, 75% yield).

GC-Mass (Theoretical value: 729.87g / mol, Measured value: 729g / mol)

[ Synthesis Example  13] Synthesis of R187

614.1 g (18.0 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.2 g (19.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.5 g (54.1 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R187, (14.0, 13.5 mmol, yield 75%).

GC-Mass (Theoretical value: 1037.22g / mol, Measured value: 1037g / mol)

[ Synthesis Example  14] Synthesis of R207

6.3 g (17.1 mmol) A1- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the target compound R207, (8.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 627.73g / mol, Measured value: 627g / mol)

[ Synthesis Example  15] Synthesis of R210

10.9 g (17.1 mmol) A11, 2-bromo-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine, 9.2 g (18.8 mmol) under nitrogen stream ), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 ° C. for 3 hours. It was.

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 was purified by column chromatography to give the title compound R210, (8.4g, 12.8 mmol, yield 75%).

GC-Mass (Theoretical value: 655.70g / mol, Measured value: 655g / mol)

[ Synthesis Example  16] Synthesis of R227

7.6 g (17.1 mmol) A2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R227, (9.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 703.83g / mol, Measured value: 703g / mol)

[ Synthesis Example  17] Synthesis of R247

8.9 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R267, (10.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 780.91g / mol, Measured value: 780g / mol)

[ Synthesis Example  18] Synthesis of R236

8.9 g (17.1 mmol) A2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R267, (10.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 780.91g / mol, Measured value: 780g / mol)

[ Synthesis Example  19] Synthesis of R287

15.8 g (19.0 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.9 g (57.0 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R287, (15.5g, 14.3 mmol, 75% yield).

GC-Mass (Theoretical value: 1087.27 g / mol, Measured value: 1087 g / mol)

[ Synthesis Example  20] Synthesis of R307

6.3 g (17.1 mmol) A2, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R307, (8.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 627.73g / mol, Measured value: 627g / mol)

[ Synthesis Example  21] Synthesis of R310

6.3 g (17.1 mmol) A16, 2-bromo-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine, 9.2 g (18.8 mmol) under nitrogen stream ), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 ° C. for 3 hours. It was.

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 was purified by column chromatography to give the title compound R310, (8.4g, 12.8 mmol, yield 75%).

GC-Mass (Theoretical value: 655.70g / mol, Measured value: 655g / mol)

[ Synthesis Example  22] Synthesis of R347

7.6 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R347, (9.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 703.83g / mol, Measured value: 703g / mol)

[ Synthesis Example  23] Synthesis of R367

A18 15.8 g (19.0 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.9 g (57.0 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R367, (15.5g, 14.3 mmol, 75% yield).

GC-Mass (Theoretical value: 1087.27 g / mol, Measured value: 1087 g / mol)

[ Synthesis Example  24] Synthesis of R387

6.3 g (17.1 mmol) A2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R387, (8.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 627.73g / mol, Measured value: 627g / mol)

[ Synthesis Example  25] Synthesis of R390

6.3 g (17.1 mmol) A16, 2-bromo-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine, 9.2 g (18.8 mmol) under nitrogen stream ), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 ° C. for 3 hours. It was.

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 was purified by column chromatography to give the title compound R390, (8.4g, 12.8 mmol, yield 75%).

GC-Mass (Theoretical value: 655.70g / mol, Measured value: 655g / mol)

[ Synthesis Example  26] Synthesis of 407

7.6 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R407, (9.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 703.83g / mol, Measured value: 703g / mol)

[ Synthesis Example  27] Synthesis of R427

15.8 g (19.0 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.7 g (20.9 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.9 g (57.0 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R427, (15.5g, 14.3 mmol, 75% yield).

GC-Mass (Theoretical value: 1087.27 g / mol, Measured value: 1087 g / mol)

[ Synthesis Example  28] Synthesis of 447

5.4 g (17.1 mmol) A2, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R447, (7.4g, 12.8 mmol, yield 75%).

GC-Mass (Theoretical value: 576.69g / mol, Measured value: 576g / mol)

[ Synthesis Example  29] Synthesis of 467

6.7 g (17.1 mmol) A2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R467, (8.0g, 12.3 mmol, 72% yield).

GC-Mass (Theoretical value: 652.78g / mol, Measured value: 652g / mol)

[ Synthesis Example  30] Synthesis of 487

7.2 g (18.3 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.3 g (20.1 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.6 g (54.8 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol 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 was purified by column chromatography to give the title compound R487, (8.6g, 13.2 mmol, 72% yield).

GC-Mass (Theoretical value: 652.78g / mol, Measured value: 652g / mol)

[ Synthesis Example  31] Synthesis of 507

14.25 g (18.3 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.3 g (20.1 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.6 g (54.8 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol 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 was purified by column chromatography to give the title compound R507, (14.6g, 13.2 mmol, 72% yield).

GC-Mass (Theoretical value: 1112.32g / mol, Measured value: 1112g / mol)

[ Synthesis Example  32] Synthesis of 527

6.3 g (17.1 mmol) A2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R527, (8.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 626.75g / mol, Measured value: 626g / mol)

[ Synthesis Example  33] Synthesis of 567

6.3 g (17.1 mmol) A2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R567, (8.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 626.75g / mol, Measured value: 626g / mol)

[ Synthesis Example  34] Synthesis of 587

6.3 g (17.1 mmol) A2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R587, (8.0g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 626.75g / mol, Measured value: 626g / mol)

[ Synthesis Example  35] Synthesis of 607

5.5 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R607, (7.4g, 12.8 mmol, 75% yield).

GC-Mass (Theoretical value: 577.67 g / mol, Measured value: 577 g / mol)

[ Synthesis Example  36] Synthesis of 687

5.9 g (17.1 mmol) A2, 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.1 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added thereto and 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 was purified by column chromatography to give the title compound R687, (7.4g, 12.3 mmol, 72% yield).

GC-Mass (Theoretical value: 603.75g / mol, Measured value: 603g / mol)

[ Synthesis Example  37] Synthesis of 767

6.1 g (18.3 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 9.3 g (20.1 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.6 g (54.8 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol 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 was purified by column chromatography to give the title compound R767, (7.8g, 13.2 mmol, 72% yield).

GC-Mass (Theoretical value: 593.74g / mol, Measured value: 593g / mol)

[ Synthesis Example  38] Synthesis of 807

5.5 g (17.1 mmol), 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, 8.7 g (18.8 mmol), 1.0 under nitrogen stream g (5 mol%) of Pd (PPh ₃ ) ₄ , potassium carbonate, 7.0 g (51.2 mmol), and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol 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 was purified by column chromatography to give the target compound R807, (7.4g, 12.8 mmol, yield 75%).

GC-Mass (Theoretical value: 578.86 g / mol, Measured value: 578 g / mol)

[ Example  1 to 37] green organic Electric 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 EL device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / R7, R10, R13, R125, R27, R47, R67, R87, R107, R127, R147, R167, R187, R207, R210, on the prepared ITO transparent electrode Each compound of R227, R247, R267, R287, R307, R310, R347, R367, R387, R390, R407, R427, R447, R467, R507, R527, R567, R587, R607, R687, R767, R487 + 10% An organic electroluminescent device was manufactured by laminating 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 Fabrication of Green Organic Electroluminescent Device

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

[Evaluation Example 1]

For each of the green organic electroluminescent devices fabricated in Examples 1 to 37 and Comparative Example 2, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. Indicated.

Sample	Host	Drive 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 compounds according to the present invention (R7, R10, R13, R125, R27, R47, R67, R87, R107, R127, R147, R167, R187, R207, R210, R227, R247, R267, When R287, R307, R310, R347, R367, R387, R390, R407, R427, R447, R467, R507, R527, R567, R587, R607, R687, R767, R487) are used as the light emitting layer of the green organic electroluminescent device. (Examples 1 to 37) Compared with the green organic electroluminescent device (Comparative Example 1) using the conventional CBP, it can be seen that it shows better performance in terms of efficiency and driving voltage.

Examples 38 to 48 Fabrication of Blue Organic Electroluminescent Devices

The compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate for 5 minutes using UV And the substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, DS-205 (Doosan Electronics 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / R7, R10, R13, R207, R287 , R447, R527, R607, R687, R767 (5 nm) / Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to manufacture an organic EL device.

Comparative Example 2 Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 38, except for depositing Alq ₃ , which is an electron transporting layer material, at 30 nm instead of 25 nm as an electron transporting auxiliary material.

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

Comparative Example 3 Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 38, except that A1 of the following structural formula was used instead of R7 as the electron transport auxiliary layer material.

[Evaluation Example 2]

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

Sample	Electron transport auxiliary layer	Driving voltage (V)	Light emitting 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 in the electron transport auxiliary layer are blue organic electroluminescent devices without the electron transport auxiliary layer (Comparative Examples 2 and 3). Compared with the current efficiency, the light emission peak and the driving voltage it was found that excellent performance.

Examples 49 to 59 Fabrication of Blue Organic Electroluminescent Devices

The compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.

first. A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / R10, R13, R207, R287, Compounds of R447, R527, R607, R687, R767, and R807 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked to prepare an organic EL device.

Comparative Example 4 Fabrication of Blue Organic Electroluminescent Device

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

Comparative Example 5 Fabrication of Blue Organic Electroluminescent Device

A blue organic EL device was manufactured in the same manner as in Example 49, except that R7 was not used as the electron transporting material.

[Evaluation Example 3]

For the blue organic electroluminescent devices fabricated in Examples 49 to 59 and Comparative Examples 2 and 3, respectively, driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below. Indicated.

Sample	Electron transport layer	Driving voltage (V)	Light emitting 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 above, the blue organic electroluminescent devices (Examples 49 to 59) using the compound of the present invention in the electron transporting layer are the blue organic electroluminescent devices (Comparative Example 4) using the conventional Alq ₃ in the electron transporting layer and Compared with the blue organic electroluminescent element (Comparative Example 5) without an electron transport layer, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.

The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

Claims (17)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In Chemical 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 one of formulas 2 to 4;

   [Formula 2]

   

   [Formula 3]

   

   [Formula 4]

   

   In Chemical Formulas 1 to 4,

   The dotted line means the part where condensation takes place;

   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 Formula 5, and when there are a plurality of R ₁ , they are the same as or different from each other;

    [Formula 5]

   

   In Chemical Formula 5,

   * Means the part where the bond is made;

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

   R ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha A silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

   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 The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently 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 nuclear atom having 5 to 60 heteroaryl groups, a C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When unsubstituted or substituted with one or more substituents selected from the group consisting of arylsilyl groups, they are the same as or different from each other.
2. The method of claim 1,

   The compound is represented by any one of the following Formulas 6 to 11, Compound:

   [Formula 6]

   

   [Formula 7]

   

   [Formula 8]

   

   [Formula 9]

   

   [Formula 10]

   

   [Formula 11]

   

   In Chemical Formulas 6 to 11,

   Rings A and Ar ₁ to Ar ₄ are each as defined in claim 1.
3. The method of claim 2,

   The compound is represented by any one of Chemical Formulas 6 and 8 to 11.
4. The method of claim 1,

   Ar ₁ to Ar ₄ are each independently a C ₆ ~ C ₆₀ aryl group or a nuclear atom of 5 to 60 heteroaryl group,

   The aryl group and heteroaryl group of Ar ₁ to Ar ₄ are each independently C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ aryl group and 5 to 60 nuclear atoms And when unsubstituted or substituted with one or more substituents selected from the group consisting of heteroaryl groups, they are the same or different from one another.
5. The method of claim 4, wherein

   Ar ₁ to Ar ₄ are each independently a phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorenyl group, spiro Selected from the group consisting of a fluorenyl group and a dibenzodioxyyl group,

   The phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorenyl group and spirofluorenyl group of Ar ₁ to Ar ₄ And dibenzodioxynyl groups are each independently methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, naphthalenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, and di When substituted or unsubstituted with one or more substituents selected from the group consisting of a benzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxyyl group, and substituted with a plurality of substituents, Different compounds.
6. The method of claim 1,

   Wherein L ₁ and L ₂ are each independently a direct bond or a linker represented by any one of Formulas A-1 to A-6:

   

   In Chemical Formulas A-1 to A-6,

   * Means 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 which are bonded as a linker in Formula A-1 is C (Ar ₅ ), wherein Ar ₅ is absent;

   Any one of Z ₁ to Z ₄ and Z ₅ to Z ₈ which are bonded as a linker in Formula A-3 is C (Ar ₅ ), wherein Ar ₅ is absent;

   Any one of Z ₁ to Z ₄ which is bonded as a linker in Formula A-4 is C (Ar ₅ ), wherein Ar ₅ is absent;

   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 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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 Or when Ar ₈ is a plurality, they are the same as or different from each other;

   An alkyl group, 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 of Ar ₅ to Ar ₉ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 Aryl boron group of ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When unsubstituted or substituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other.
7. The method of claim 1,

   Wherein L ₁ and L ₂ are each independently a direct bond or a linker represented by any one of Formulas B-1 to B-11:

   

   In Chemical Formulas B-1 to B-11,

   * Means the part where the bond is made;

   Ar ₆ to Ar ₉ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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;

   The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of Ar ₆ to Ar ₉ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 Aryl boron group of ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When unsubstituted or substituted with one or more substituents, and 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.
9. The method of claim 1,

   R ₂ is a substituent represented by Formula 12:

   [Formula 12]

   

   In Chemical Formula 12,

   * Means the part where the bond is made;

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

   Ar ₁₀ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha A silyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group, and when there are a plurality of Ar ₁₀ , they are the same or different from each other;

   An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of Ar ₁₀ , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ 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,

    The substituent represented by Formula 12 is a substituent represented by the following formula (13):

    [Formula 13]

    

    In Chemical Formula 13,

    * Means the part where the bond is made;

    R ₃ and R ₄ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₃ and R ₄ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other;

    Y ₁ , Y ₃ and Y ₅ are each as defined in claim 9.
11. The method of claim 9,

    The substituent represented by Formula 12 is a substituent represented by any one of the following Formulas C-1 to C-5:

    

    In Chemical Formulas C-1 to C-5,

    * Means the part where the coupling is made,

    R ₃ and R ₄ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₃ and R ₄ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
12. The method of claim 10,

    R ₃ and R ₄ are each independently selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms,

    The alkyl group, aryl group and heteroaryl group of R ₃ and R ₄ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same or different from each other.
13. The method of claim 1,

    R ₂ is a substituent represented by Formula 14:

    [Formula 14]

    

    In Chemical Formula 14,

    * Means the part where the bond is made;

    R ₅ and R ₆ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron 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 group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₅ and R ₆ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , 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 or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
14. The method of claim 13,

    R ₅ and R ₆ are each independently selected from the group consisting of an alkyl group having ₁ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms,

    The alkyl group, aryl group and heteroaryl group of R ₅ and R ₆ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same or different from each other.
15. The method of claim 1,

    The compound is selected from the group consisting of the following compounds:

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    

    
16. An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,

    At least one of the one or more organic material layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1) of claim 1.
17. The method of claim 16,

    The organic material layer includes an organic electroluminescent device comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer and a light emitting layer.

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