WO2017099430A1 - Organic compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising same. The compound, according to the present invention, is usable in an organic layer, and desirably in an electron transport layer or an electron transport auxiliary layer in the organic electroluminescent device, thereby enhancing light-emitting efficiency, driving voltage, and life, among other characteristics, of the organic electroluminescent device.

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,

L ₁ to L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₆₀ carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;

R ₁ to 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;

The arylene group and heteroarylene group of L ₁ to L ₄ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R ₁ to R ₄ , Arylamine 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 alkyl groups, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryl jade group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono or diarylphosphinyl 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, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, 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 such as N, O, S or Se. In addition, a form in which two or more rings are simply attached or condensed with each other may be included, and is also construed to include a form condensed with an aryl group. 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 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 Chemical Formula 1 according to the present invention exhibits high efficiency device characteristics due to excellent electrical stability and tilted structural properties.

In particular, when the compound represented by Formula 1 of the present invention is used in the electron transport layer and the electron transport auxiliary layer, it is possible to manufacture an organic electroluminescent device having a low driving voltage, high efficiency and long life compared to the conventional electron transport material, Furthermore, full-color display panels with significantly improved performance and longevity can be manufactured.

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

L ₁ to L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₆₀ carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;

R ₁ to 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;

The arylene group and heteroarylene group of L ₁ to L ₄ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R ₁ to R ₄ , Arylamine 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 alkyl groups, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryl jade group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono or diarylphosphinyl 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 compound according to the present invention has a structure in which various fluorene groups and hetero rings are bonded to a binaphthalene moiety. Electron-withdrawing electrons (EWGs) with high electron absorption such as aromatic rings (eg phenyl, fluorene) or nitrogen-containing heterocycles (eg pyrimidine, triazine, quinazoline, quinoline, triazolopyridinyl, etc.) It forms the basic backbone connected by various linkers (phenyl, biphenyl, naphthalene, fluorene, carbazolyl, phenanthrene, etc.). Specifically, it is characterized in that the compound represented by the formula (1).

[Formula 1]

In Chemical Formula 1,

L ₁ to L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₆₀ carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;

R ₁ to 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;

The arylene group and heteroarylene group of L ₁ to L ₄ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R ₁ to R ₄ , Arylamine 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 alkyl groups, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryl jade group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono or diarylphosphinyl 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.

By using the compound of the present invention as a material for the electron transporting layer or the electron transporting auxiliary layer of the organic light emitting device, it is possible to improve the efficiency and life characteristics of the organic light emitting device. In addition, the compound of the present invention can improve the life characteristics by the center of the binaphthalene structure, the binaphthalene has a steric hindrance by the substitution structure, thereby having a high triplet energy, excitons generated in the light emitting layer to the light emitting layer Diffusion to adjacent electron transporting layers or hole transporting layers can be prevented. The number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased.

According to one preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by any one of the following Formulas 2 to 4:

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,

L ₁ to L ₄ , R ₁ to R ₄ are each as defined in Chemical Formula 1.

According to one preferred embodiment of the present invention, L ₁ to L ₄ 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 one preferred embodiment of the present invention, each of R ₁ to R ₄ may be independently selected from the group consisting of hydrogen and a substituent represented by the formula 5 to 17:

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

In Chemical Formulas 5 to 17,

* Means the part where the bond is made;

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

In Formula 6, and 8 L _1, L _2, L ₃ or L ₄ Z ₁ to Z ₄ which one is coupled to, Z _1, or coupled by the formula (9) to L _1, L _2, L ₃ or L ₄ Z ₂ , in Formulas 11 and 14, any one of Z ₃ to Z ₆ bonded to L ₁ , L ₂ , L _3, or L ₄ is C (R ₅ ), wherein R ₅ is absent;

T ₁ is N (R ₆ ) or C (R ₇ ) (R ₈ );

When T ₁ is bonded to L ₁ , L ₂ , L ₃ or L ₄ in Formulas 8 and 9, when T ₁ is N (R ₆ ), R ₆ is absent, or T ₁ is C (R ₇ ) (R ₈ ) any one of R ₇ and R ₈ is absent;

Y ₁ is N or C (R ₅ );

R ₅ to R ₈ 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 ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ aryl boron groups, C ₆ to aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, the adjacent groups (e. g., L _1, L _2, adjacent to the C ₆₀ Another R ₅ , R _6, R ₇ or R ₈ ) may form a condensed ring, and when there are a plurality of R ₅ , they may be the same or different from each other;

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 ₅ to R ₈ 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 a preferred embodiment of the present invention, each of R ₁ to R ₄ is independently selected from the group consisting of hydrogen and substituents represented by the following formula F-1 to F-17 to the organic electroluminescent device When applied, it is preferred for, but not limited to, extending life, improving luminous efficiency, and lowering driving voltage:

In Chemical Formulas F-1 to F-17,

m is an integer from 0 to 4;

n is an integer from 0 to 3;

p is an integer from 0 to 2;

R ₉ 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 ₆ ~ C ₆₀ aryl group, nuclear atom C ₅ to C ₆₀ aryloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, A C ₆ -C ₆₀ mono or diarylphosphinyl group and C ₆ -C ₆₀ arylsilyl group, or an adjacent group (e.g., L ₁ , L ₂ , adjacent R ₅ to R ₈ , Or may be combined with another R ₉ ) to form a condensed ring, and when there are a plurality of R ₉ , 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 R ₉ , 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 If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other,

* And R ₅ to R ₈ are as defined in the formula 5 to 17.

According to a preferred embodiment of the present invention, wherein R ₁ and R ₂ are each independently a substituent selected from the group consisting of F-3, F-5, F-6, F-14 and F-15 When applied to the organic electroluminescent device, it is more preferable in extending the life, improving the luminous efficiency and lowering the driving voltage.

According to one preferred embodiment of the present invention, each of R ₅ to R ₉ is independently hydrogen, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected from the group.

According to a preferred embodiment of the present invention, R ₅ to R ₉ are each independently hydrogen, phenyl group, biphenyl group, naphthalenyl group, carbazolyl group, fluorenyl group, pyridinyl group and pyrimidinyl group Can be selected.

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 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. Preferably, the organic material layer including the compound represented by Chemical Formula 1 may be an electron transport layer or an electron transport auxiliary layer.

The compound represented by the formula (1) of the present invention can improve the life characteristics by the central binaphthalene structure, the binaphthalene has a steric hindrance by the substitution structure, thereby having a high triplet energy, generated in the light emitting layer The excitons can be prevented from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. The number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased. Therefore, by using the compound of Formula 1 of the present invention as a material for the electron transporting layer or the electron transporting auxiliary layer of the organic light emitting device, it is possible to improve the efficiency and the life characteristics of the organic light emitting device.

Meanwhile, according to an example of the present invention, the light emitting layer of the organic EL device may include a host material, and in this case, the host material may include the compound represented by Formula 1 above. 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 an electron transport layer or an electron transport aid The layer may include a compound represented by Chemical Formula 1.

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 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 is a material known in the art, except that at least one of the organic material layers (for example, an electron transporting layer or an electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 above. And other organic material layers and electrodes using the method.

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] DIA Synthesis of -1

<Step 1> 2- (4- Chlorophenyl Synthesis of) -4,6-diphenyl-1,3,5-triazine

2-chloro-4,6-diphenyl-1,3,5-triazine (37g, 0.14mol) and (4-chlorophenyl) boronic acid (23.8g, 0.15mol) were completely dissolved in 150ml THF and then 2M K ₂ CO ₃ (80 ml) was added, Pd (PPh ₃ ) ₄ (3.2 g, 2.7 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. Lower the temperature to room temperature, remove the water layer, dry with MgSO ₄ , concentrate under reduced pressure and column with THF: Hex = 1: 6 to give the target compound, 2-chloro-4,6-diphenyl-1,3,5-triazine. (34g, yield: 72%) was obtained.

[LCMS]: 344

<Step 2> 2,4-diphenyl-6- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran Synthesis of 2-yl) phenyl) -1,3,5-triazine

2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (34g, 98.9mmol) and bis (pinacolato) diboron (27.6g, 108mmol) and KOAc under nitrogen stream (29.1 g, 296 mmol) were added and added to 100 ml of dioxane and heated with stirring. Pd (dba) ₃ (1.7 g, 2.94 mmol) and P (Cy) ₃ (1.6 g, 5.9 mmol) were added thereto under reflux, and the mixture was heated and stirred for 10 hours. After the reaction was completed, the temperature was lowered to room temperature and filtered. The filtrate was poured into water and extracted with chloroform, and the organic layer was extracted with MgSO ₄ Dried over. After distillation under reduced pressure, recrystallization with ethanol gave the title compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Phenyl) -1,3,5-triazine (35 g, yield: 81%) was prepared.

[LCMS]: 435

<Step 3> 2- (2'- Bromo -[1,1'- Vinaphthalene ] -2-yl) -4,4,5,5- Tetramethyl Synthesis of -1,3,2-dioxaborolane

2,2'-Dibromo-1,1'-vinaphthalene (30.0 g, 72.7 mmol) and bis (pinacolato) diboron (20.3 g, 79.9 mmol) and KOAc (21.3 g, 218 mmol) under a nitrogen stream Were mixed and 150 ml of dioxane was added and stirred. Pd (dppf) Cl ₂ (2.65 g, 3.6 mmol) was added thereto and stirred for 10 hours. After the reaction was completed the reaction was filtered. The filtrate was poured into water and extracted with chloroform, and the organic layer was extracted with MgSO ₄ Dried over. After concentration under reduced pressure, MC: Hex = 1: 3, and the column was subjected to 2- (2'-bromo- [1,1'-vinaphthalen] -2-yl) -4,4,5,5-tetra as a target compound. Methyl-1,3,2-dioxaborolane (16.4 g, yield: 55%) was obtained.

[LSMS]: 412

<Step 4> 2- (4- (2'- Bromo -[1,1'- Vinaphthalene ] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine

2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (30 g, 87.2 mmol) and 2- (2'-bromo- [1,1'-ratio under nitrogen stream Naphthalene] -2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (40 g, 87.2 mmol) and Cs ₂ CO ₃ (56 g, 174.4 mmol) are mixed and toluene After adding 200ml, 50ml of ethanol and 50ml of water, Pd (OAc) ₂ (970mg, 4.3mmol) and Xphos (4.1g, 8.7mmol) were added thereto, followed by heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and filtered. The filtrate was poured into water and extracted with chloroform, and the organic layer was extracted with MgSO ₄ Dried over. After concentration under reduced pressure, MC: Hex = 1: 3, and the column was subjected to 2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6- Diphenyl-1,3,5-triazine (24 g, yield: 43%) was obtained.

[LCMS]: 640

<Step 5> 4- (4- Chlorophenyl ) -2,6- Diphenylpyrimidine  synthesis

Compound 2-chloro-4,6-di except that 4-chloro-2,6-diphenylpyrimidine was used instead of compound 2-chloro-4,6-diphenyl-1,3,5-triazine The compound 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (12 g, yield: 82%) was obtained by the same method as the method for preparing phenyl-1,3,5-triazine.

[LCMS]: 343

<Step 6> 4-([1,1'-biphenyl] -4-yl) -6- (4- Chlorophenyl )-2- Of phenylpyrimidine  synthesis

4-([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine in place of the compound 2-chloro-4,6-diphenyl-1,3,5-triazine Except for the use of the compound 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as the preparation of the compound 4-([1,1'-biphenyl] -4- Il) -6- (4-chlorophenyl) -2-phenylpyrimidine (10 g, yield: 77%) was obtained.

[LCMS]: 419

<Step 7> 2-([1,1'-biphenyl] -4-yl) -4- (4- Chlorophenyl Synthesis of 6-phenyl-1,3,5-triazine

2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 3,5-triazine, the compound 2-([1,1 ') in the same manner as the method for preparing the compound 2-chloro-4,6-diphenyl-1,3,5-triazine -Biphenyl] -4-yl) -4- (4-chlorophenyl) -6-phenyl-1,3,5-triazine (12 g, yield: 82%) was obtained.

[LCMS]: 420

<Step 8> 2,4-diphenyl-6- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran Synthesis of 2-yl) phenyl) pyrimidine

Except for the use of 4- (4-chlorophenyl) -2,6-diphenylpyrimidine instead of compound 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5- Compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2- in the same manner as the method for preparing triazine Il) phenyl) pyrimidine (11 g, yield: 80%) was obtained.

[LCMS]: 434

<Step 9> 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6- (4- (4,4,5,5- Tetramethyl Synthesis of -1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine

4-([1,1'-biphenyl] -4-yl) -6- (4- instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaboro, except that chlorophenyl) -2-phenylpyrimidine was used The compound 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6 in the same manner as the preparation of lan-2-yl) phenyl) -1,3,5-triazine. -(4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine (13 g, yield: 82%) was obtained.

[LCMS]: 510

<Step 10> 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (4- (4,4,5,5- Tetramethyl Synthesis of -1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine

2-([1,1'-biphenyl] -4-yl) -4- (4- instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine The compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3 except for using chlorophenyl) -6-phenyl-1,3,5-triazine Compound 2-([1,1'-biphenyl] -4-yl in the same manner as the method for preparing, 2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine ) -4-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine (10 g, yield: 79%) was obtained.

[LCMS]: 511

<Step 11> 2- (4'- Bromo -[1,1'- Vinaphthalene ] -4-yl) -4,4,5,5- Tetramethyl Synthesis of -1,3,2-dioxaborolane

Compound 2- (2'-bromo, except that 4,4'-dibromo-1,1'-binaphthalene was used instead of compound 2,2'-dibromo-1,1'-binaphthalene -[1,1'-Vinaphthalene] -2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane in the same manner as the method for preparing compound 2- (4'-Bromo- [1,1'-vinaphthalen] -4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15 g, yield: 42 %) Was obtained.

[LCMS]: 459

<Step 12> 2- (6'- Bromo -[1,1'- Vinaphthalene ] -6-day) -4,4,5,5- Tetramethyl Synthesis of -1,3,2-dioxaborolane

Compound 2- (2'-bromo, except that 6,6'-dibromo-1,1'-binaphthalene was used instead of compound 2,2'-dibromo-1,1'-binaphthalene -[1,1'-Vinaphthalene] -2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane in the same manner as the method for preparing compound 2- (6'-Bromo- [1,1'-vinaphthalene] -6-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (22 g, yield: 48 %) Was obtained.

[LCMS]: 459

<Step 13> 4-([1,1'-biphenyl] -4-yl) -6- (4- (2'- Bromo -[1,1'- Vinaphthalene ] -2-yl) phenyl) -2-phenylpyrimidine

4-([1,1'-biphenyl] -4-yl) -6- (4- instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine The compound 2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-di except for using chlorophenyl) -2-phenylpyrimidine The compound 4-([1,1'-biphenyl] -4-yl) -6- (4- (2'-bromo-) by the same method as the method for preparing phenyl-1,3,5-triazine. [1,1'-Vinaphthalene] -2-yl) phenyl) -2-phenylpyrimidine (11 g, yield: 62%) was obtained.

[LCMS]: 716

<Step 14> 2-([1,1'-biphenyl] -4-yl) -4- (4- (2'- Bromo -[1,1'- Vinaphthalene ] -2-yl) phenyl) -6-phenyl-1,3,5-triazine

4-([1,1'-biphenyl] -4-yl) -6- (4- instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine The compound 2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-di except for using chlorophenyl) -2-phenylpyrimidine Compound 2-([1,1'-biphenyl] -4-yl) -4- (4- (2'-bromo-) by the same method as for producing phenyl-1,3,5-triazine. [1,1'-Vinaphthalene] -2-yl) phenyl) -6-phenyl-1,3,5-triazine (15 g, yield: 58%) was obtained.

[LCMS]: 717

<Step 15> 2- (4- (4'- Bromo -[1,1'- Vinaphthalene ] -4-yl) phenyl) -4,6-diphenyl-1,3,5-triazine

2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-tri instead of the compound 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5- except that azine was used Compound 2- (4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -4,6-diphenyl-1, in the same manner as the method for preparing triazine, 3,5-triazine (13 g, yield: 57%) was obtained.

[LCMS]: 640

<Step 16> 4-([1,1'-biphenyl] -4-yl) -6- (4- (4'- Bromo -[1,1'- Vinaphthalene ] -4-yl) phenyl) -2-phenylpyrimidine

4-([1,1'-biphenyl] -4-yl) -6- (4- instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine The compound 2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-di except for using chlorophenyl) -2-phenylpyrimidine The compound 4-([1,1'-biphenyl] -4-yl) -6- (4- (4'-bromo-) by the same method as the method for preparing phenyl-1,3,5-triazine. [1,1'-Vinaphthalene] -4-yl) phenyl) -2-phenylpyrimidine (16 g, yield: 62%) was obtained.

[LCMS]: 716

<Step 17> 2-([1,1'-biphenyl] -4-yl) -4- (4- (4'- Bromo -[1,1'- Vinaphthalene ] -4-yl) phenyl) -6-phenyl-1,3,5-triazine

2-([1,1'-biphenyl] -4-yl) -4- (4- instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl, except for using chlorophenyl) -6-phenyl-1,3,5-triazine ) -4,6-diphenyl-1,3,5-triazine in the same manner as the method for preparing compound 2-([1,1'-biphenyl] -4-yl) -4- (4- (4'-Bromo- [1,1'-binaphthalene] -4-yl) phenyl) -6-phenyl-1,3,5-triazine (14 g, yield: 65%) was obtained.

[LCMS]: 717

<Step 18> 2- (4- (6'- Bromo -[1,1'- Vinaphthalene ] -6-yl) phenyl) -4,6-diphenyl-1,3,5-triazine

2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-tri instead of the compound 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5- except that azine was used Compound 2- (4- (6'-bromo- [1,1'-binaphthalene] -6-yl) phenyl) -4,6-diphenyl-1, in the same manner as the method for preparing triazine, 3,5-triazine (11 g, yield: 42%) was obtained.

[LCMS]: 640

<Step 19> 4-([1,1'-biphenyl] -4-yl) -6- (4- (6'- Bromo -[1,1'- Vinaphthalene ] -6-yl) phenyl) -2-phenylpyrimidine

4-([1,1'-biphenyl] -4-yl) -6- (4- instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine The compound 2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-di except for using chlorophenyl) -2-phenylpyrimidine The compound 4-([1,1'-biphenyl] -4-yl) -6- (4- (6'-bromo-) by the same method as the method for preparing phenyl-1,3,5-triazine. [1,1'-Vinaphthalene] -6-yl) phenyl) -2-phenylpyrimidine (14 g, yield: 52%) was obtained.

[LCMS]: 716

<Step 20> 2-([1,1'-biphenyl] -4-yl) -4- (4- (6'- Bromo -[1,1'- Vinaphthalene ] -6-yl) phenyl) -6-phenyl-1,3,5-triazine

2-([1,1'-biphenyl] -4-yl) -4- (4- instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl, except for using chlorophenyl) -6-phenyl-1,3,5-triazine ) -4,6-diphenyl-1,3,5-triazine in the same manner as the method for preparing compound 2-([1,1'-biphenyl] -4-yl) -4- (4- (6'-Bromo- [1,1'-binaphthalene] -6-yl) phenyl) -6-phenyl-1,3,5-triazine (17 g, yield: 61%) was obtained.

[LCMS]: 717

[ Synthesis Example  1] Synthesis of A-1

2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine (12 g, under a stream of nitrogen) 18.7 mmol) and 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine (8.1 g, 18.7 mmol) and K ₂ CO ₃ (5.1 g, 37.4 mmol) were mixed, 150 ml of dioxane and 30 ml of water were added, Pd (PPh ₃ ) ₄ (1 g, 0.9 mmol) was added and heated for 4 hours, Stirred. After the reaction was completed, the temperature was lowered to room temperature and filtered. The filtrate was poured into water and extracted with chloroform, and the organic layer was extracted with MgSO ₄ Dried over. Concentration under reduced pressure and then MC: Hex = 1: 3 to give the compound A-1 (6.1g, yield: 37%).

[LCMS]: 868

[ Synthesis Example  2] Synthesis of A-2

2- (instead of compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine [1,1'-biphenyl] -4-yl) -4-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- Compound A-2 (4.2 g, yield: 46%) was obtained by the same method as the method of preparing compound A-1, except that one) phenyl) -1,3,5-triazine was used.

[LCMS]: 945

[ Synthesis Example  3] Synthesis of A-3

The compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine instead of 4- ( [1,1'-biphenyl] -4-yl) -2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- Compound A-3 (6.9 g, yield: 43%) was obtained by the same method as the method for preparing compound A-1, except that one) phenyl) pyrimidine was used.

[LCMS]: 944

[ Synthesis Example  4] Synthesis of A-4

The compound 2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 4- ( [1,1'-biphenyl] -4-yl) -6- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -2-phenylpyrimidine 4-, instead of 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine ([1,1'-biphenyl] -4-yl) -2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2 Compound A-4 (5.2 g, yield: 44%) was obtained by the same method as the method for preparing compound A-1, except that -yl) phenyl) pyrimidine was used.

[LCMS]: 944

[ Synthesis Example  5] Synthesis of A-16

2- (instead of compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound A-1 was prepared except that 9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used. Compound A-16 (7.2 g, yield: 62%) was obtained in the same manner as the method described above.

[LCMS]: 830

[ Synthesis Example  6] Synthesis of A-17

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( [1,1'-biphenyl] -4-yl) -4- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -6-phenyl-1, 3,5-triazine was used and 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Except for using 2- (9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of phenyl) pyrimidine Compound A-17 (3.4 g, yield: 54%) was obtained in the same manner as the method for preparing compound A-1.

[LCMS]: 906

[ Synthesis Example  7] Synthesis of A-18

The compound 2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 4- ( [1,1'-biphenyl] -4-yl) -6- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -2-phenylpyrimidine 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine instead of 2- Compound A-1, except that (9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used. Compound A-18 (6.3 g, yield: 53%) was obtained in the same manner as the preparation method.

[LCMS]: 905

[ Synthesis Example  8] Synthesis of A-19

1-phenyl instead of compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound A-1, except that -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo [d] imidazole was used Compound A-19 (4.5 g, yield: 53%) was obtained in the same manner as the preparation method.

[LCMS]: 830

[ Synthesis Example  9] Synthesis of A-20

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( [1,1'-biphenyl] -4-yl) -4- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -6-phenyl-1, 3,5-triazine was used and 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) 1-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo [d] imidazole instead of phenyl) pyrimidine Compound A-20 (6.6 g, yield: 42%) was obtained by the same method as the method of preparing compound A-1, except that.

[LCMS]: 906

[ Synthesis Example  10] Synthesis of A-21

The compound 2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 4- ( [1,1'-biphenyl] -4-yl) -6- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -2-phenylpyrimidine 1, instead of 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound A- except that phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo [d] imidazole was used. Compound A-21 (7.1 g, yield: 72%) was obtained by the same method as the method for preparing 1.

[LCMS]: 905

[ Synthesis Example  11] Synthesis of B-1

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( Compound A-, except that 4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -4,6-diphenyl-1,3,5-triazine was used Compound B-1 (7.9 g, yield: 72%) was obtained by the same method as the method for preparing 1.

[LCMS]: 868

[ Synthesis Example  12] Synthesis of B-2

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( 4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -4,6-diphenyl-1,3,5-triazine was used and 2,4-di 2-([1,1'-ratio) instead of phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Phenyl] -4-yl) -4-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1, Compound B-2 (12 g, yield: 63%) was obtained by the same method as the method of preparing compound A-1, except that 3,5-triazine was used.

[LCMS]: 945

[ Synthesis Example  13] Synthesis of B-3

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( 4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -4,6-diphenyl-1,3,5-triazine was used and 2,4-di 4-([1,1'-ratio instead of phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Phenyl] -4-yl) -2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound B-3 (5.2 g, yield: 42%) was obtained by the same method as the method for preparing compound A-1, except that used.

[LCMS]: 944

[ Synthesis Example  14] Synthesis of B-16

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( 4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -4,6-diphenyl-1,3,5-triazine was used and 2,4-di 2- (9,9-dimethyl-9H instead of phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine -Fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane, except that Compound A-1 was prepared in the same manner as above. Compound B-16 (6.2 g, yield: 54%) was obtained.

[LCMS]: 830

[ Synthesis Example  15] Synthesis of B-17

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( [1,1'-biphenyl] -4-yl) -4- (4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -6-phenyl-1, 3,5-triazine was used and 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Except for using 2- (9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of phenyl) pyrimidine Compound B-17 (7.2 g yield: 67%) was obtained in the same manner as the method for preparing compound A-1.

[LCMS]: 906

[ Synthesis Example  16] Synthesis of B-18

The compound 2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 4- ( [1,1'-biphenyl] -4-yl) -6- (4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -2-phenylpyrimidine 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine instead of 2- Compound A-1, except that (9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used. Compound B-18 (8.2 g, yield: 65%) was obtained by the same method as the preparation method.

[LCMS]: 905

[ Synthesis Example  17] Synthesis of B-19

The compound 2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 4- ( 4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -2,6-diphenylpyrimidine was used and 2,4-diphenyl-6- (4- 1-phenyl-6- (4,4,5,5-tetramethyl instead of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound B-19 in the same manner as for preparing Compound A-1, except that -1,3,2-dioxaborolan-2-yl) -1H-benzo [d] imidazole was used. 4.3 g, yield: 52%).

[LCMS]: 830

[ Synthesis Example  18] Synthesis of B-20

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( [1,1'-biphenyl] -4-yl) -4- (4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -6-phenyl-1, 3,5-triazine was used and 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) 1-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo [d] imidazole instead of phenyl) pyrimidine Compound B-20 (5.3 g, yield: 52%) was obtained by the same method as the method of preparing compound A-1, except that.

[LCMS]: 906

[ Synthesis Example  19] Synthesis of B-21

The compound 2- (4- (2'-bromo- [1,1'-binaphthalen] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 4- ( [1,1'-biphenyl] -4-yl) -6- (4- (4'-bromo- [1,1'-binaphthalene] -4-yl) phenyl) -2-phenylpyrimidine 1, instead of 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound A- except that phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo [d] imidazole was used. Compound B-21 (4.7 g, yield: 43%) was obtained by the same method as the method for preparing 1.

[LCMS]: 905

[ Synthesis Example  20] Synthesis of C-1

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( Compound A-, except that 4- (6'-bromo- [1,1'-binaphthalene] -6-yl) phenyl) -4,6-diphenyl-1,3,5-triazine was used Compound C-1 (6.2 g, yield: 48%) was obtained by the same method as the method for preparing 1.

[LCMS]: 868

[ Synthesis Example  21] Synthesis of C-2

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( 4- (6'-bromo- [1,1'-binaphthalene] -6-yl) phenyl) -4,6-diphenyl-1,3,5-triazine was used and 2,4-di 2-([1,1'-ratio) instead of phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Phenyl] -4-yl) -4-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1, Compound C-2 (5.9 g, yield: 42%) was obtained by the same method as the method for preparing compound A-1, except that 3,5-triazine was used.

[LCMS]: 945

[ Synthesis Example  22] Synthesis of C-3

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( 4- (6'-bromo- [1,1'-binaphthalene] -6-yl) phenyl) -4,6-diphenyl-1,3,5-triazine was used and 2,4-di 4-([1,1'-ratio instead of phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Phenyl] -4-yl) -2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound C-3 (6.2 g, yield: 52%) was obtained by the same method as the method for preparing compound A-1, except for the use.

[LCMS]: 944

[ Synthesis Example  23] C- 16 of  synthesis

2- (4- (2'-bromo- [1,1'-binaphthalene] -2-yl) phenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- ( 4- (6'-bromo- [1,1'-binaphthalene] -6-yl) phenyl) -4,6-diphenyl-1,3,5-triazine was used and 2,4-di 4-([1,1'-ratio instead of phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Phenyl] -4-yl) -2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound C-3 (6.2 g, yield: 52%) was obtained by the same method as the method for preparing compound A-1, except for the use.

[LCMS]: 944

[ Synthesis Example  24] Synthesis of C-16

2- (instead of compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound A-1 was prepared except that 9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used. Compound C-16 (7.3 g, yield: 63%) was obtained in the same manner as the method described above.

[LCMS]: 830

[ Synthesis Example  25] Synthesis of C-19

1-phenyl instead of compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine Compound A-1, except that -6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo [d] imidazole was used Compound C-19 (5.2 g, yield: 53%) was obtained in the same manner as the preparation method.

[LCMS]: 830

[ Example  1 to 18] blue organic Electric field  Manufacture of light emitting device

Compounds A-1, A-2, A-3, A-4, A-16, A-19, A-20, A-21, B-1, B-2, and B synthesized in Synthesis Examples 1 to 25 After high purity sublimation purification of -16, B-17, B-18, B-19, B-20, C-1, C-16, C-19 by a commonly known method, blue organic electroluminescence as follows The device was produced.

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 prepared ITO transparent electrode, DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30nm) / Compound A-1, A-2 , A-3, A-4, A-16, A-19, A-20, A-21, B-1, B-2, B-16, B-17, B-18, B-19, B Compounds of -20, C-1, C-16 or C-19 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.

[ Comparative example  1] blue organic Electric field  Manufacture of light emitting device

A blue organic EL device was manufactured in the same manner as in Example 1, except that Alq ₃ was used instead of Compound A-1 as the electron transporting layer material.

[ Comparative example  2] blue organic Electric field  Manufacture of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1 was not used as the electron transporting layer material.

The structures of NPB, AND and Alq 3 used in Examples 1 to 18 and Comparative Examples 1 and 2 are as follows.

[Evaluation Example 1]

For the blue organic electroluminescent devices fabricated in Examples 1 to 18 and Comparative Examples 1 and 2, the 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 1 below. Indicated.

Sample Electron transport layer Driving voltage (V) Light emitting peak (nm) Current efficiency (cd / A) Example 1 Compound A-1 4.1 457 7.6 Example 2 Compound A-2 3.8 456 8.1 Example 3 Compound A-3 3.3 451 7.6 Example 4 Compound A-4 3.7 452 8.5 Example 5 Compound a-16 3.6 455 9.3 Example 6 Compound a-19 3.9 453 8.1 Example 7 Compound A-20 4.2 454 8.7 Example 8 Compound a-21 4.3 455 8.1 Example 9 Compound B-1 4.0 456 7.8 Example 10 Compound b-2 3.9 457 8.2 Example 11 Compound b-16 3.2 458 8.1 Example 12 Compound b-17 3.1 453 8.5 Example 13 Compound b-18 3.7 453 7.6 Example 14 Compound b-19 4.2 454 8.1 Example 15 Compound b-20 3.5 455 8.2 Example 16 Compound C-1 3.9 452 8.1 Example 17 Compound c-16 3.8 453 7.3 Example 18 Compound C-19 4.0 458 7.2 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 1, the blue organic electroluminescent device (Examples 1 to 18) using the compound of the present invention in the electron transporting layer is a blue organic electroluminescent device (comparative example 1) using Alq ₃ in the electron transporting layer and Compared with the blue organic electroluminescent device (Comparative Example 2) without an electron transporting layer, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.

[ Example  19 to 32] blue organic Electric field  Manufacture of light emitting device

Compounds A-2, A-4, A-17, A-19, A-21, B-1, B-3, B-16, B-19, B-21, and C synthesized in Synthesis Examples 1 to 25 -1, C-3, C-16, C-19 After a high purity sublimation purification by a conventionally known method, a blue organic electroluminescent device was manufactured by 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, Hwashin Tech), and then wash the substrate using UV for 5 minutes 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) / Compound A-2, A-4, A-17, A-19, A-21, B-1, B-3, B-16, B-19, B-21, C-1, C-3, C-16, C-19 (5 nm ) / Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare an organic EL device.

[ Comparative example  3] blue organic Electric field  Manufacture of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 19, except that Compound A-2 was not used as an electron transport auxiliary layer material, and Alq ₃ , which was an electron transport layer material, was deposited at 30 nm instead of 25 nm. Produced.

[Evaluation Example 2]

For the organic electroluminescent devices manufactured in Examples 19 to 32 and Comparative Example 3, the driving voltage, the light emission wavelength, and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

Sample Electronic transport auxiliary layer Drive voltage (V) Emission Peak (nm) Current efficiency (cd / A) Example 19 Compound A-2 4.1 455 8.1 Example 20 Compound A-4 3.7 451 7.6 Example 21 Compound a-17 3.9 454 7.7 Example 22 Compound a-19 3.9 453 7.3 Example 23 Compound a-21 3.7 455 8.3 Example 24 Compound B-1 3.8 452 8.1 Example 25 Compound b-3 3.7 458 7.9 Example 26 Compound b-16 4.3 454 7.8 Example 27 Compound b-19 4.2 455 8.6 Example 28 Compound b-21 3.4 456 8.1 Example 29 Compound C-1 3.9 458 8.3 Example 30 Compound c-3 3.9 459 7.8 Example 31 Compound c-16 4.1 455 7.5 Example 32 Compound C-19 4.4 454 8.6 Comparative Example 3 - 4.8 458 6.0

As shown in Table 2, the blue organic electroluminescent devices (Examples 19 to 32) using the compound of the present invention in the electron transport auxiliary layer were compared to the blue organic electroluminescent devices (Comparative Example 3) without the electron transport auxiliary layer. It was found to exhibit excellent performance in terms of current efficiency, emission peak, 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 (9)

Compound represented by the following formula (1): [Formula 1]

In Chemical Formula 1, L ₁ to L ₄ 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; R ₁ to 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; The arylene group and heteroarylene group of L ₁ to L ₄ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R ₁ to R ₄ , Arylamine 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 alkyl groups, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryl jade group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ mono or diarylphosphinyl 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 method of claim 1, Compound represented by Formula 1 is a compound represented by any one of the following formulas 2 to 4: [Formula 2]

[Formula 3] [Formula 4]

In Chemical Formulas 2 to 4, L ₁ to L ₄ and R ₁ to R ₄ are each as defined in claim 1. The method of claim 1, L ₁ to L ₄ 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. The method of claim 1, R ₁ to R ₄ are each independently hydrogen and a compound selected from the group consisting of substituents represented by the following formulas 5 to 17: [Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

In Chemical Formulas 5 to 17, * Means the part where the bond is made; Z ₁ to Z ₈ are each independently N or C (R ₅ ); In Formula 6, and 8 L _1, L _2, L ₃ or L ₄ Z ₁ to Z ₄ which one is coupled to, Z _1, or coupled by the formula (9) to L _1, L _2, L ₃ or L ₄ Z ₂ , in Formulas 11 and 14, any one of Z ₃ to Z ₆ bonded to L ₁ , L ₂ , L _3, or L ₄ is C (R ₅ ), wherein R ₅ is absent; T ₁ is N (R ₆ ) or C (R ₇ ) (R ₈ ); When T ₁ is bonded to L ₁ , L ₂ , L _3, or L ₄ in Formulas 8 and 9, R ₆ is absent or any one of R ₇ and R ₈ is absent; Y ₁ is N or C (R ₅ ); R ₅ to R ₈ 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 ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ aryl boron groups, C ₆ to aryl phosphazene group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ of the C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, the groups bonded to or adjacent to which they are attached may form a condensed ring , When there are a plurality of R ₅ , they are the same or different from each other; 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 ₅ to R ₈ 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. The method of claim 1, R ₁ to R ₄ are each independently hydrogen and a substituent selected from the group consisting of Formulas F-1 to F-17:

In Chemical Formulas F-1 to F-17, * Means the part where the bond is made; m is an integer from 0 to 4; n is an integer from 0 to 3; p is an integer from 0 to 2; R ₅ to R ₈ 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 ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ aryl boron groups, C ₆ to aryl phosphazene group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ of the C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups bond to form a fused ring, and ; R ₉ 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 ₆ ~ C ₆₀ aryl group, nuclear atom C ₅ to C ₆₀ aryloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group selected from the group, or may be combined with adjacent groups to form a condensed ring, when there are a plurality of R ₉ They are the same or different from each other; 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 ₅ to R 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 ~ 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. The method of claim 5, R ₅ to R ₉ 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. The method of claim 1, The compound is selected from the group consisting of the following compounds:

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. The method of claim 8, 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.