WO2017099431A1 - Organic compound and organic electroluminescent device containing same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device containing the same. The compound according to the present invention is used in an organic layer of an organic electroluminescent device, preferably, in a light emitting layer, thereby enabling the luminous efficiency, driving voltage, lifespan and the like of the organic electroluminescent device to 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.

Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose's organic thin-film emission, followed by Tang in 1987. ), An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer is 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.

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , 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 the organic material layer material which is excellent in performance is calculated | required.

In order to solve the above problems, an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.

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 to X ₇ are each independently N or C (R ₂ ), but at least one of X ₁ to X ₇ is N;

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

Ar ₁ is an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, an alkyloxy group of C ₁ ~ C ₄₀ , an aryloxy group of C ₆ ~ C ₆₀ , 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;

n is an integer from 0 to 5;

R ₁ is 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, nuclear atom 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 _An alkylsilyl group of ₃ to C ₄₀ , an arylsilyl group of C ₆ to C ₆₀ , an alkyl boron group of C ₁ to C _40, an aryl boron group of C ₆ to C ₆₀ , an arylphosphanyl group of C ₆ to C ₆₀ , C ₆ ~ C _{60 It} is selected from the group consisting of mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group, when there are a plurality of R ₁ They are the same or different from each other;

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, and when there are a plurality of R ₂ , they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, of Ar ₁ , R ₁ and R ₂ , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron 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 of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to 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 _When substituted or unsubstituted with one or more substituents selected from the group consisting of ₆ to C ₆₀ arylsilyl groups, and substituted with a plurality of substituents, they may be the same 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 C2-C40 straight or branched chain unsaturated hydrocarbon 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 at least one carbon-carbon triple bond, 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; Polycides such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl Click 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 to 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 of 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.

The compound represented by Formula 1 according to the present invention is excellent in thermal stability, hole transporting, hole injection performance, electron transporting and electron injection performance, and excellent phosphorescence characteristics of the light emitting layer, so that the organic material layer material of the organic electroluminescent device, preferably May be used as the light emitting layer material.

In particular, when using the novel compound represented by the formula (1) of the present invention as a light emitting layer material, it is possible to manufacture an organic electroluminescent device having excellent luminous performance, low driving voltage, high efficiency and long life compared to the conventional material, furthermore, performance and lifespan This greatly improved full color display panel can also be manufactured.

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

X ₁ to X ₇ are each independently N or C (R ₂ ), but at least one of X ₁ to X ₇ is N;

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

Ar ₁ is an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, an alkyloxy group of C ₁ ~ C ₄₀ , an aryloxy group of C ₆ ~ C ₆₀ , 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;

n is an integer from 0 to 5;

R ₁ is 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, nuclear atom 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 _An alkylsilyl group of ₃ to C ₄₀ , an arylsilyl group of C ₆ to C ₆₀ , an alkyl boron group of C ₁ to C _40, an aryl boron group of C ₆ to C ₆₀ , an arylphosphanyl group of C ₆ to C ₆₀ , C ₆ ~ C _{60 It} is selected from the group consisting of mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group, when there are a plurality of R ₁ They are the same or different from each other;

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, and when there are a plurality of R ₂ , they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, of Ar ₁ , R ₁ and R ₂ , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron 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 of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to 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 _When substituted or unsubstituted with one or more substituents selected from the group consisting of ₆ to C ₆₀ arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

The novel organic compounds according to the invention have an azacarbazole skeleton in which phenyl is substituted at position 1 of the carbazole. The azacarbazole moiety has a high T1 and a wide band gap, so that energy transfer to the dopant may be useful, thereby improving luminous efficiency of the device. Specifically, the novel organic compound according to the present invention is characterized in that the compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

X ₁ to X ₇ are each independently N or C (R ₂ ), but at least one of X ₁ to X ₇ is N;

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

Ar ₁ is an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, an alkyloxy group of C ₁ ~ C ₄₀ , an aryloxy group of C ₆ ~ C ₆₀ , 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;

n is an integer from 0 to 5;

R ₁ is 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, nuclear atom 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 _An alkylsilyl group of ₃ to C ₄₀ , an arylsilyl group of C ₆ to C ₆₀ , an alkyl boron group of C ₁ to C _40, an aryl boron group of C ₆ to C ₆₀ , an arylphosphanyl group of C ₆ to C ₆₀ , C ₆ ~ C _{60 It} is selected from the group consisting of mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group, when there are a plurality of R ₁ They are the same or different from each other;

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, and when there are a plurality of R ₂ , they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, of Ar ₁ , R ₁ and R ₂ , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron 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 of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to 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 _When substituted or unsubstituted with one or more substituents selected from the group consisting of ₆ to C ₆₀ arylsilyl 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, the compound represented by Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 2 to 8:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Chemical Formulas 2 to 8,

Y ₁ to Y ₇ are all C (R ₃ ), but a plurality of R ₃ are the same as or different from each other;

A plurality of R _{3 's} 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 groups, 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 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 phosphazene aryl group, a mono- or diaryl the C ₆ ~ C ₆₀ Phosphinicosuccinic group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

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 R ₃ , 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, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl Substituted with a substituent being unsubstituted or, if substituted by a plurality of substituents, these are the same or may be different from one another, and;

Ar _{1 ,} R ₁ , L ₁ , L ₂ and n are each as defined in Chemical Formula 1.

According to a preferred embodiment of the present invention, L ₁ and L ₂ may be independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group and a carbazolyl group.

According to a preferred embodiment of the present invention, Ar ₁ and R ₂ are each independently hydrogen, C ₁ ~ C ₄₀ Alkyl group, C ₆ ~ C ₆₀ An aryl group and a nuclear atom of 5 to 60 heteroaryl group Can be selected from the group.

According to one embodiment, it preferred according to the present invention, when at least one of the Ar ₁ and R ₂ to the substituent formula (9) may be a substituent represented by the displayed the Ar ₁ and R ₂ are to both a general formula (9), all of which are It can be the same or different from each other:

[Formula 9]

In Chemical Formula 9,

* Means the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₄ );

L ₃ is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

R ₄ 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 R ₄ , they are the same or different from each other;

Alkyl groups of the L ₃ of the arylene group and a heteroarylene group, R _4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkyl Silyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy groups, C ₆ to C ₆₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl yarn Substituted with one or more substituents selected from the group consisting of a ring or unsubstituted and, if 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, specific examples of the substituent represented by Formula 9 include a substituent represented by the following A-1 to A-16, but is not limited thereto:

In Chemical Formulas A-1 to A-16,

R ₄ 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 Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group selected from the group consisting of a plurality of R ₄ in the formula A-1 to A-10 are the same or different from each other To;

m is an integer of 0 to 4, and when m is 0, it means that hydrogen is not substituted with a substituent R ₅ , and when m is an integer of 1 to 4, R ₅ is deuterium, halogen, cyano group, nitro C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ ~ C ₆₀ , alkyloxy group of C ₁ ~ C ₄₀ , arylamine group of C ₆ ~ C ₆₀ , C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C of ₆ ~ C ₆₀ mono or diaryl phosphine When selected from the group consisting of a pinyl group and C ₆ ~ C ₆₀ arylsilyl group, or may be combined with an adjacent group (for example, R ₄ or other R _5, etc.) to form a condensed ring, when there are a plurality of R ₅ These are synonymous with each other Or different and;

Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₄ and R ₅ 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 may be the same or different from each other;

* And L ₃ are each as defined in Chemical Formula 9.

According to one preferred embodiment of the present invention, in the substituent represented by Formula 9, R ₄ may be a C ₆ ~ C ₆₀ aryl group or a nuclear atom of 5 to 60 heteroaryl group.

According to a preferred embodiment of the present invention, in the substituent represented by the formula (9), R ₄ may be selected from the group consisting of phenyl group, biphenyl group, fluorenyl group and carbazolyl group.

According to a preferred embodiment of the present invention, L ₃ may be selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group and a carbazolyl group.

According to one embodiment, preferred according to the present invention, when at least one of the Ar ₁ and R ₂ to the substituent formula (10) may be a substituent represented by the above Ar ₁ and R ₂ are represented by the formula (10) to both, all of which are It can be the same or different from each other:

[Formula 10]

In Chemical Formula 10,

* Means the part where the bond is made;

L ₄ is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

R ₆ and R ₇ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of the Or R ₆ and R ₇ may combine to form a condensed ring;

The arylene group and heteroarylene group of L ₄ and the alkyl group, aryl group, heteroaryl group and arylamine group of R ₆ and R ₇ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to 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 may be the same or different from each other.

According to a preferred embodiment of the present invention, in the substituent represented by Formula 10, R ₆ and R ₇ may be each independently a C ₆ ~ C ₆₀ aryl group or a nuclear atom of 5 to 60 heteroaryl group. .

According to a preferred embodiment of the present invention, in the substituent represented by Formula 10, R ₆ and R ₇ may be each independently selected from the group consisting of phenyl group, biphenyl group, fluorenyl group and carbazolyl group.

According to a preferred embodiment of the present invention, L ₄ may be selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group and a carbazolyl group.

According to one embodiment, preferred according to the present invention, when at least one of the Ar ₁ and R ₂ to the substituent represented by the following be a substituent. However, the Ar ₁ and R ₂ are both represented by formula (11) formula (11), all of which are It can be the same or different from each other:

[Formula 11]

In Chemical Formula 11,

* Means the part where the bond is made;

T ₁ is selected from the group consisting of O, S, N (R ₈ ) and C (R ₉ ) (R ₁₀ ),

R ₈ to R ₁₀ 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 the above R ₈ to R ₁₀ 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 of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

According to one embodiment, the preferred of the invention, in the substituent represented by the formula 11, wherein R ₈ to R ₁₀ are each independently hydrogen, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₆ It may be selected from the group consisting of an aryl group of ~ C _{60 and} a heteroaryl group of 5 to 60 nuclear atoms.

According to a preferred embodiment of the present invention, in the substituent represented by Formula 11, wherein R ₈ to R ₁₀ are each independently hydrogen, methyl, ethyl, propanyl, butyl, phenyl, phenyl, biphenyl, naph It may be selected from the group consisting of a thalenyl group and a pyridinyl group.

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

In the present invention, the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. 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 at least one organic material layer may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic material layer may include a compound represented by Formula 1 above. Can be. Preferably, the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer.

According to an example of the present invention, the light emitting layer of the organic EL device may include a host material, and may include a compound represented by Chemical Formula 1 as a host material, in particular, a green host material. As such, when the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.

The structure of the organic EL device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer. In the present invention, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer is represented by the formula (1) It may include a compound represented.

In addition, the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more layers of organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

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

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

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy 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  One] PPI Synthesis of -1

<Step 1> 3- (2- Nitrophenyl ) -5- Phenylpyridine  synthesis

(5-phenylpyridin-3-yl) boronic acid (19.9 g, 100.0 mmol), 1-bromo-2-nitrobenzene (20.2 g, 100.0 mmol), Pd (PPh ₃ ) ₄ under nitrogen stream (5.78 g, 5 mol%) and NaOH (12.0 g, 300.0 mmol) were added to 1000 ml / 500 ml of THF / H ₂ O and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound 3- (2-nitrophenyl) -5-phenylpyridine (24.7 g, 89% yield).

Mass: [(M + H) ⁺ ]: 277

Elemental Analysis: C, 73.90; H, 4.38; N, 10.14; O, 11.58

<Step 2> PPI Synthesis of -1

Under nitrogen stream, 3- (2-nitrophenyl) -5-phenylpyridine (13.3 g, 60.0 mmol) and triphenylphosphine (47.2 g, 180.0 mmol) were added to 500 ml of 1,2-dichlorobenzene at 12O <0> C. Stir for hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the organic layer filtered to obtain the target compound PPI-1 (4.85 g, yield 33%) by column chromatography.

Mass: [(M + H) ⁺ ]: 245

¹ H-NMR: δ 7.20 (t, 1H), 7.43 (m, 3H), 7.51 (m, 3H), 7.63 (d, 1H), 8.17 (d, 1H), 9.00 (s, 1H), 9.25 ( s, 1 H), 11.54 (s, 1 H)

[ Preparation  2] PPI Synthesis of -2

<Step 1> 3- (5- Chloro -2- Nitrophenyl ) -5- Phenylpyridine  synthesis

<Step of Preparation Example 1, except that 2-bromo-4-chloro-1-nitrobenzene (23.6 g, 100.0 mmol) was used instead of 1-bromo-2-nitrobenzene (20.2 g, 100.0 mmol) 1> was carried out in the same manner to obtain 3- (5-chloro-2-nitrophenyl) -5-phenylpyridine (26.4 g, yield 85%).

Mass: [(M + H) ⁺ ]: 311

Elemental Analysis: C, 65.71; H, 3.57; Cl, 11.41; N, 9.02; O, 10.30

<Step 2> 8- Chloro -4-phenyl-5H- Of pyrido [4,3-b] indole  synthesis

Except for using 3- (5-chloro-2-nitrophenyl) -5-phenylpyridine (18.7 g, 60.0 mmol) instead of 3- (2-nitrophenyl) -5-phenylpyridine (13.3 g, 60.0 mmol) Subsequently, 8-chloro-4-phenyl-5H-pyrido [4,3-b] indole (6.86 g, 41% yield) was obtained by the same process as <Step 2> of Preparation Example 1.

Mass: [(M + H) ⁺ ]: 279

Elemental Analysis: C, 73.25; H, 3.98; Cl, 12.72; N, 10.05

<Step 3> PPI Synthesis of -2

8-chloro-4-phenyl-5H-pyrido [4,3-b] indole (5.58 g, 20.0 mmol), iodine benzene (12.2 g, 60.0 mmol), Cu powder (0.05 g, 2.00 mmol) under nitrogen stream , K ₂ CO ₃ (8.28 g, 60.0 mmol) was added to nitrobenzene (100 ml) and stirred at 190 ° C. for 12 hours. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with 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 PPI-2 (6.04 g, yield 85%).

Mass: [(M + H) ⁺ ]: 355

¹ H-NMR: δ 7.09 (d, 1H), 7.46 (m, 3H), 7.52 (m, 4H), 7.59 (m, 3H), 7.87 (d, 1H), 8.07 (s, 1H), 8.95 ( s, 1 H), 9.19 (s, 1 H)

[ Preparation  3] PPI Synthesis of -3

<Step 1> PPI Synthesis of -3

8-chloro-4-phenyl-5H-pyrido [4,3-b] indole (5.58 g, 20.0 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1, under nitrogen stream 3,5-triazine (11.65 g, 30.0 mmol), Pd ₂ (dba) ₃ (0.92 g, 1.0 mmol), (t-Bu) ₃ P (0.40 g, 2.0 mmol), sodium tert-butoxide (5.98 g, 60.0 mmol) was added to 200 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound PPI-3 (9.02 g, yield 77%).

Mass: [(M + H) ⁺ ]: 586

¹ H-NMR: δ 7.11 (d, 1H), 7.45 (m, 3H), 7.51 (m, 8H), 7.62 (m, 2H), 7.88 (d, 1H), 7.99 (s, 1H), 8.22 ( m, 2H), 8.34 (d, 4H), 9.00 (s, 1H), 9.26 (s, 1H)

[ Preparation  4] PPI Synthesis of -4

<Step 1> 2-([1,1'-biphenyl] -3-yl) -6- Chloro -3- Nitropyridone  synthesis

[1,1'-biphenyl] -3-ylboronic acid (19.8 g, 100.0 mmol), 2-bromo-6-chloro-3-nitropyridine (23.7 g, 100.0 mmol), Pd (PPh) under nitrogen stream ₃ ) ₄ (5.78 g, 5 mol%) and NaOH (12.0 g, 300.0 mmol) were added to 1000 ml / 500 ml of THF / H ₂ O and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to the target compound 2-([1,1'-biphenyl] -3-yl) -6-chloro-3-nitropyridine (25.2 g, yield 81% ) Was obtained.

Mass: [(M + H) ⁺ ]: 311

Elemental Analysis: C, 65.71; H, 3.57; Cl, 11.41; N, 9.02; O, 10.30

<Step 2> 2- Chloro -6-phenyl-5H- Of pyrido [3,2-b] indole  synthesis

2-([1,1'-biphenyl] -3-yl) -6-chloro-3-nitropyridine (18.7 g) instead of 3- (2-nitrophenyl) -5-phenylpyridine (13.3 g, 60.0 mmol) , 60.0 mmol) was subjected to the same procedure as in <Step 2> of Preparation Example 1, except that 2-chloro-6-phenyl-5H-pyrido [3,2-b] indole (6.53 g, yield) 39%).

Mass: [(M + H) ⁺ ]: 279

Elemental Analysis: C, 73.25; H, 3.98; Cl, 12.72; N, 10.05

<Step 3> PPI Synthesis of -4

2-chloro-6-phenyl-5H-pyrido [3,2-b] indole (5.58) instead of 8-chloro-4-phenyl-5H-pyrido [4,3-b] indole (5.58 g, 20.0 mmol) g, 20.0 mmol) was obtained in the same manner as in <Step 1> of Preparation Example 3, to obtain PPI-4 (9.26 g, yield 79%).

Mass: [(M + H) ⁺ ]: 586

¹ H-NMR: δ 7.19 (m, 4H), 7.30 (d, 1H), 7.45 (m, 2H), 7.51 (m, 6H), 7.62 (m, 2H), 8.22 (m, 2H), 8.36 ( m, 5H), 8.42 (d, 1H), 8.84 (d, 1H)

[ Synthesis Example  1] Synthesis of C 3

PPI-1 (2.44 g, 10.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.0 mmol), Pd ₂ (dba) ₃ (0.46 g) under nitrogen stream , 0.5 mmol), (t-Bu) ₃ P (0.20 g, 1.0 mmol) and sodium tert-butoxide (2.94 g, 30.0 mmol) were added to 100 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound C 3 (3.52 g, yield 74%) by column chromatography.

Mass: [(M + H) ⁺ ]: 476

[ Synthesis Example  2] Synthesis of C 5

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using), the same procedure as in Synthesis Example 1 was carried out to obtain a target compound C 5 (4.53 g, yield 82%).

Mass: [(M + H) ⁺ ]: 552

[ Synthesis Example  3] Synthesis of C 15

PPI-3 (5.86 g, 10.0 mmol), phenyl boronic acid (1.22 g, 10.0 mmol), K ₂ CO ₃ under nitrogen stream (4.27 g, 30.0 mmol), Pd (PPh ₃ ) ₄ (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) were added with 120 ml / 40 ml / 40 ml of Tol / EtOH / H ₂ O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the organic layer filtered to obtain the target compound C 15 (3.89 g, yield 62%) by column chromatography.

Mass: [(M + H) ⁺ ]: 628

[ Synthesis Example  4] Synthesis of C 23

PPI-2 (3.55 g, 10.0 mmol) under nitrogen stream, (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol), K ₂ CO ₃ (4.27 g, 30.0 mmol), Pd (PPh ₃ ) ₄ (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) were added with 120 ml / 40 ml / 40 ml of Tol / EtOH / H ₂ O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound C 23 (4.21 g, yield 67%).

Mass: [(M + H) ⁺ ]: 628

[ Synthesis Example  5] Synthesis of C 35

PPI-3 (5.86 g, 10.0 mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.00 mmol), K ₂ CO ₃ under nitrogen stream (4.27 g, 30.0 mmol), Pd (PPh ₃ ) ₄ (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) were added with 120 ml / 40 ml / 40 ml of Tol / EtOH / H ₂ O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound C 35 (5.55 g, yield 70%) by column chromatography.

Mass: [(M + H) ⁺ ]: 793

[ Synthesis Example  6] Synthesis of C 45

The use of dibenzo [b, d] thiophen-2-ylboronic acid (2.28 g, 10.00 mmol) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.00 mmol) Except for the same procedure as in Synthesis Example 5 to obtain the title compound C 45 (4.84 g, 66% yield).

Mass: [(M + H) ⁺ ]: 734

[ Synthesis Example  7] Synthesis of C 50

Except for using dibenzo [b, d] furan-2-ylboronic acid (2.12 g, 10.00 mmol) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.00 mmol) Then, the same procedure as in Synthesis Example 5 was performed to obtain C 50 (4.95 g, yield 69%) as a target compound.

Mass: [(M + H) ⁺ ]: 718

[ Synthesis Example  8] Synthesis of C 55

(9,9-dimethyl-9H-fluoren-3-yl) boronic acid (2.38 g, 10.00 mmol) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.00 mmol) Except for using the same procedure as in Synthesis Example 5 to obtain the title compound C 55 (4.76 g, 64% yield).

Mass: [(M + H) ⁺ ]: 744

[ Synthesis Example  9] Synthesis of C 59

(9- (3- (4,6-diphenyl-) instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol) 1,3,5-triazin-2-yl) phenyl) -9H-carbazol-3-yl) boronic acid (5.18 g, 10.00 mmol) was subjected to the same procedure as in Synthesis Example 4, except that C 59 (6.34 g, Yield 80%) was obtained as the target compound.

Mass: [(M + H) ⁺ ]: 793

[ Synthesis Example  10] Synthesis of C 65

PPI-4 (5.86 g, 10.0 mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.0 mmol), K ₂ CO ₃ under nitrogen stream (4.27 g, 30.0 mmol), Pd (PPh ₃ ) ₄ (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) were added with 120 ml / 40 ml / 40 ml of Tol / EtOH / H ₂ O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound C 65 (4.84 g, 61% yield).

Mass: [(M + H) ⁺ ]: 793

[ Synthesis Example  11] Synthesis of C 75

The use of dibenzo [b, d] thiophen-2-ylboronic acid (2.28 g, 10.00 mmol) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.0 mmol) Except for the same procedure as in Synthesis Example 10, to obtain a target compound C 75 (5.43 g, 74% yield).

Mass: [(M + H) ⁺ ]: 734

[ Synthesis Example  12] Synthesis of C 80

Except for using dibenzo [b, d] furan-2-ylboronic acid (2.12 g, 10.00 mmol) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.0 mmol) Then, the same process as in Synthesis Example 10 was carried out to obtain a target compound C 80 (4.67 g, 65% yield).

Mass: [(M + H) ⁺ ]: 718

[ Synthesis Example  13] Synthesis of C 85

(9,9-dimethyl-9H-fluoren-3-yl) boronic acid (2.38 g, 10.00 mmol) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.0 mmol) Except for using the same procedure as in Synthesis Example 10 to obtain the target compound C 85 (5.06 g, yield 68%).

Mass: [(M + H) ⁺ ]: 744

[ Synthesis Example  14] Synthesis of C 104

(4- (di ([1,1'-biphenyl) instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol) ] -4-yl) amino) phenyl) boronic acid (4.41 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 4 to obtain the title compound C 104 (3.87 g, yield 54%). .

Mass: [(M + H) ⁺ ]: 716

[ Synthesis Example  15] Synthesis of C 105

(4-([1,1'-biphenyl]-instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol) Except for using 4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid (4.81 g, 10.00 mmol), the same procedure as in Synthesis Example 4 was performed. Phosphorus C 105 (4.46 g, yield 59%) was obtained.

Mass: [(M + H) ⁺ ]: 756

[ Example  1 to 15] green organic Electric field  Fabrication of light emitting device

Compounds C 3 to C 105 synthesized in Synthesis Examples 1 to 15 were 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., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / C 3 to C 105 + 10% Ir (ppy) ₃ (300nm) / BCP (10 nm) / Alq ₃ ( 30 nm) / LiF (1 nm) / Al (200 nm) was laminated to fabricate an organic EL device.

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 Compound C 3 as a light emitting host material when forming the emission layer.

[Evaluation Example]

For each of the green organic electroluminescent devices fabricated in Examples 1 to 15 and Comparative Example 1, 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	C 3	6.62	516	39.6
Example 2	C 5	6.71	517	39.9
Example 3	C 15	6.51	518	39.5
Example 4	C 23	6.80	518	40.1
Example 5	C 35	6.72	517	40.2
Example 6	C 45	6.72	516	41.8
Example 7	C 50	6.73	517	40.7
Example 8	C 55	6.70	518	40.2
Example 9	C 59	6.69	518	39.8
Example 10	C 65	6.70	517	39.9
Example 11	C 75	6.44	518	39.5
Example 12	C 80	6.81	517	41.1
Example 13	C 85	6.60	518	41.3
Example 14	C 104	6.71	515	43.4
Example 15	C 105	6.72	516	42.2
Comparative Example 1	CBP	6.93	516	38.2

As shown in Table 1, when the compounds (C 3 ~ C 105) according to the present invention is used as the light emitting layer of the green organic electroluminescent device (Examples 1 to 15) Green organic electroluminescent device using a conventional CBP (Comparative Compared with Example 1) it can be seen that the better performance in terms of efficiency and driving voltage.

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 (14)

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

   [Formula 1]

   

   In Chemical Formula 1,

   X ₁ to X ₇ are each independently N or C (R ₂ ), but at least one of X ₁ to X ₇ is N;

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

   Ar ₁ is an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, an alkyloxy group of C ₁ ~ C ₄₀ , an aryloxy group of C ₆ ~ C ₆₀ , 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;

   n is an integer from 0 to 5;

   R ₁ is 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, nuclear atom 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 _An alkylsilyl group of ₃ to C ₄₀ , an arylsilyl group of C ₆ to C ₆₀ , an alkyl boron group of C ₁ to C _40, an aryl boron group of C ₆ to C ₆₀ , an arylphosphanyl group of C ₆ to C ₆₀ , C ₆ ~ C _{60 It} is selected from the group consisting of mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group, when there are a plurality of R ₁ They are the same or different from each other;

   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, and when there are a plurality of R ₂ , they are the same or different from each other;

   The arylene group and heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, of Ar ₁ , R ₁ and R ₂ , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron 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 of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to 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 _When substituted or unsubstituted with one or more substituents selected from the group consisting of ₆ to C ₆₀ arylsilyl groups, and substituted with a plurality of substituents, they may be the same or different from each other.
2. The method of claim 1,

   The compound represented by Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 2 to 8:

   [Formula 2]

   

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   [Formula 8]

   

   In Chemical Formulas 2 to 8,

   Y ₁ to Y ₇ are all C (R ₃ ), but a plurality of R ₃ are the same as or different from each other;

   A plurality of R _{3 's} 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 groups, 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 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 phosphazene aryl group, a mono- or diaryl the C ₆ ~ C ₆₀ Phosphinicosuccinic group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

   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 R ₃ , 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, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl Substituted with a substituent being unsubstituted or, if substituted by a plurality of substituents, these are the same or may be different from one another, and;

   Ar _{1 ,} R ₁ , L ₁ , L ₂ and n are each as defined in claim 1.
3. The method of claim 1,

   L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group and a carbazolyl group.
4. The method of claim 1,

   Ar ₁ and R ₂ are each independently hydrogen, C ₁ ~ C ₄₀ Alkyl group, C ₆ ~ C ₆₀ An aryl group and a nuclear atom of 5 to 60 heteroaryl group selected from the group consisting of.
5. The method of claim 1,

   At least one of Ar ₁ and R ₂ is a compound represented by the formula (9):

   [Formula 9]

   

   In Chemical Formula 9,

   * Means the part where the bond is made;

   Z ₁ to Z ₅ are each independently N or C (R ₄ );

   L ₃ is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

   R ₄ 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 R ₄ , they are the same or different from each other;

   Alkyl groups of the L ₃ of the arylene group and a heteroarylene group, R _4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkyl Silyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy groups, C ₆ to C ₆₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl yarn Substituted with one or more substituents selected from the group consisting of a ring or unsubstituted and, if substituted with a plurality of substituents, they may be the same or different from each other.
6. The method of claim 5,

   The substituent represented by Formula 9 is a compound represented by any one of the following formulas A-1 to A-16:

   

   In Chemical Formulas A-1 to A-16,

   R ₄ 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 Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group selected from the group consisting of a plurality of R ₄ in the formula A-1 to A-10 are the same or different from each other To;

   m is an integer of 0 to 4, and when m is 0, it means that hydrogen is not substituted with a substituent R ₅ , and when m is an integer of 1 to 4, R ₅ is deuterium, halogen, cyano group, nitro C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ ~ C ₆₀ , alkyloxy group of C ₁ ~ C ₄₀ , arylamine group of C ₆ ~ C ₆₀ , C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C of ₆ ~ C ₆₀ mono or diaryl phosphine When selected from the group consisting of a pinyl group and C ₆ ~ C ₆₀ arylsilyl group, or may be combined with an adjacent group (for example, R ₄ or other R _5, etc.) to form a condensed ring, when there are a plurality of R ₅ These are synonymous with each other Or different and;

   Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R ₄ and R ₅ 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 may be the same or different from each other;

   * And L ₃ are each as defined in claim 5.
7. The method of claim 5,

   R ₄ is a C ₆ ~ C ₆₀ An aryl group or a nuclear atom of 5 to 60 heteroaryl group.
8. The method of claim 1,

   At least one of Ar ₁ and R ₂ is a substituent represented by Formula 10:

   [Formula 10]

   

   In Chemical Formula 10,

   * Means the part where the bond is made;

   L ₄ is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

   R ₆ and R ₇ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of the Or R ₆ and R ₇ may combine to form a condensed ring;

   The arylene group and heteroarylene group of L ₄ and the alkyl group, aryl group, heteroaryl group and arylamine group of R ₆ and R ₇ are each independently deuterium, halogen, cyano group, nitro group, C ₁ to 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 may be the same or different from each other.
9. The method of claim 8,

   R ₆ and R ₇ are each independently a C ₆ ~ C ₆₀ aryl group or a nuclear atom of 5 to 60 heteroaryl group.
10. The method of claim 1,

    At least one of Ar ₁ and R ₂ is a substituent represented by Formula 11 below:

    [Formula 11]

    

    In Chemical Formula 11,

    * Means the part where the bond is made;

    T ₁ is selected from the group consisting of O, S, N (R ₈ ) and C (R ₉ ) (R ₁₀ ),

    R ₈ to R ₁₀ 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 the above R ₈ to R ₁₀ 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 of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
11. The method of claim 10,

    Wherein R ₈ to R ₁₀ are each independently hydrogen, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₆ ~ C ₆₀ aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group the group consisting of Compound selected from.
12. The method of claim 1,

    Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of:

    

    

    

    

    

    

    

    
13. 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.
14. The method of claim 13,

    The organic material layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a life improvement layer, a light emitting layer and a light emitting auxiliary layer.