WO2017209487A1 - 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, being used for an organic layer of the organic electroluminescent device, preferably, a light-emitting layer, an electron transport layer or an auxiliary electron transport layer, thereby enabling the enhancement of the light-emitting efficiency, driving voltage, life, etc. 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,

Z ₁ to Z ₃ are each independently N or C (R ₂ ), but at least two of Z ₁ to Z ₃ are N;

m is an integer from 0 to 4;

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 ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl 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 is selected from diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of, when the plurality of R ₁ individual, a plurality of R ₁ are the same or different from each other;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

R ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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;

The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl of R ₁ and R ₂ The group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, aryl phosphinyl group and aryl amine 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 ~ 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 alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When unsubstituted or substituted with one or more substituents selected from the group consisting of, these are the same or different from each other;

D is a substituent represented by the following formula (2);

n is an integer of 1 or 2, and when n is 2, the two Ds are the same or different from each other;

[Formula 2]

In Chemical Formula 2,

* Means the part where the bond is made;

Ar ₁ and Ar ₂ 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 ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl of Ar ₁ and Ar ₂ Boron group, arylphosphanyl group, arylphosphinyl group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of Substituted with ventilation or unsubstituted and, if substituted with a plurality of substituents, they are same as or different from each other.

In addition, 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 is a compound represented by the formula (1) It provides an organic electroluminescent device comprising a.

"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, carbon number may be 8 to 60), and the whole molecule is non-aromacity. Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 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 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.

Compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

Z ₁ to Z ₃ are each independently N or C (R ₂ ), but at least two of Z ₁ to Z ₃ are N;

m is an integer from 0 to 4;

R ₁ is heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, a cycloalkyl group of C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of nuclear atoms 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 ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl 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 is selected from diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of, when the plurality of R ₁ individual, a plurality of R ₁ are the same or different from each other;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

R ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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;

The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl of R ₁ and R ₂ The group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, aryl phosphinyl group and aryl amine 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 ~ 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 boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ aryl silyl group When unsubstituted or substituted with one or more substituents selected from the group consisting of, these are the same or different from each other;

D is a substituent represented by the following formula (2);

n is an integer of 1 or 2, and when n is 2, the two Ds are the same or different from each other;

[Formula 2]

In Chemical Formula 2,

* Means the part where the bond is made;

Ar ₁ and Ar ₂ 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 ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl of Ar ₁ and Ar ₂ boron group, an aryl phosphazene group, an aryl Phosphinicosuccinic group and aryl amine groups are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of Substituted with ventilation or unsubstituted and, if substituted with a plurality of substituents, they are same as or different from each other.

Hereinafter, the present invention will be described in detail.

One. New organic compounds

The novel compounds of the present invention can be represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

Z ₁ to Z ₃ are each independently N or C (R ₂ ), but at least two of Z ₁ to Z ₃ are N;

m is an integer of 0 to 4, preferably an integer of 1 or 2;

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 ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl 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 is selected from diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of, when the plurality of R ₁ individual, a plurality of R ₁ are the same or different from each other;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

R ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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;

The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl of R ₁ and R ₂ The group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, aryl phosphinyl group and aryl amine 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 ~ 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 alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When unsubstituted or substituted with one or more substituents selected from the group consisting of, these are the same or different from each other;

D is a substituent represented by the following formula (2);

n is an integer of 1 or 2, and when n is 2, the two Ds are the same or different from each other;

[Formula 2]

In Chemical Formula 2,

* Means the part where the bond is made;

Ar ₁ and Ar ₂ 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 ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl of Ar ₁ and Ar ₂ Boron group, arylphosphanyl group, arylphosphinyl group and arylamine 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 in the arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of Substituted with ventilation or unsubstituted and, if substituted with a plurality of substituents, they are same as or different from each other.

The condensation compound having excellent electronwithdrawing froup (EWG) properties represented by Formula 1 of the present invention is electrochemically stable and superior in electron mobility as well as high glass transition temperature and thermal stability compared to a six-membered heterocyclic structure. This is excellent. For this reason, the compound represented by Formula 1 of the present invention is excellent in electron transport ability and luminescence properties, the material of any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer that is an organic material layer of the organic electroluminescent device Can be used as Preferably, the light emitting layer, the electron transporting layer and the electron transporting layer further laminated on the electron transporting layer can be used as a material of any one of the material, more preferably the electron transporting layer, or the electron transporting auxiliary layer.

Therefore, when the compound represented by Formula 1 of the present invention is used in an organic electroluminescent device, not only excellent thermal stability and carrier transport ability (especially electron transport ability and light emission ability) can be expected, but also the driving voltage, efficiency, Lifespan, etc. can be improved, and the high triplet energy can represent an excellent efficiency increase due to the triplet-triplet fusion (TTF) effect as the latest ETL material.

In addition, the compound represented by the general formula (1) of the present invention is a material in which the indene derivative containing nitrogen (N) and the phosphine-oxide functional group (phosphinyl group), which are well known, are very advantageous for electron injection and have a long lifetime. Show characteristics The excellent electron transport ability can have high efficiency and fast mobility in the organic EL device.

In addition, the compound represented by the general formula (1) of the present invention is a material consisting of a combination of an indene derivative containing nitrogen (N) and a phosphine-oxide functional group (phosphinyl group) generally shows a wide band gap value of the substituent It is easy to adjust HOMO and LUMO energy levels according to the direction or location. In the organic electroluminescent device using such a compound, high electron transport can be seen.

According to one preferred embodiment of the present invention, the compound of Formula 1 may be a compound represented by the following formula (3):

[Formula 3]

In Chemical Formula 3,

R ₃ and R ₄ are each independently hydrogen, deuterium, an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C ₆ to C ₆₀ Selected from the group consisting of, R ₃ and R ₄ are not all hydrogen;

The alkyl group, aryl group, heteroaryl group and arylamine group of R ₃ and R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C Or substituted with one or more substituents selected from the group consisting of ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, and C ₆ to C ₆₀ arylamine groups Ring, and when substituted with a plurality of substituents, they may be the same or different from each other,

Z ₁ to Z ₃ , L, D and n are each as defined in Chemical Formula 1.

According to one preferred embodiment of the present invention, the compound of Formula 1 may be a compound represented by the following formula (4):

[Formula 4]

In Chemical Formula 4,

R ₁ , L, D, m and n are each as defined in Formula 1 above.

According to a preferred embodiment of the present invention, R ₁ may be selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, phenanthrenyl group and triphenylenyl group.

According to one preferred embodiment of the present invention, at least one of the R ₃ and R ₄ may be selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, phenanthrenyl group and triphenylenyl group.

According to a preferred embodiment of the present invention, L may be a linker represented by the following formula (5):

[Formula 5]

In Chemical Formula 5,

* Means the part where the bond is made;

L ₁ to L ₃ may be each independently selected from the group consisting of a single bond, a phenylene group, a pyridinyl group, and a naphthalenyl group.

Further, according to one preferred embodiment of the present invention, when n is 1, L may be a linker selected from the group consisting of A1 to A5, and when n is 2, L is in the group consisting of B1 to B4 The linker of choice may be, but is not limited to:

In A1 to A5 and B1 to B4, * means a part where a bond is made. In addition, any one of the two bond lines (ㅡ *) in A1 to A5 may bind to an indene derivative including N, and the other may bind to D. In B1 to B4, any one of the three bond lines (-*) may bind to the indene derivative including N, and the other two bond lines may bind to two Ds, which may be the same or different from each other.

According to one preferred embodiment of the present invention, Ar ₁ and Ar ₂ are each independently selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected.

According to one preferred embodiment of the present invention, Ar ₁ and Ar ₂ may be each independently represented by a substituent represented by the following formula (6):

[Formula 6]

In Chemical Formula 6,

* Means the part where the bond is made;

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

R ₅ is hydrogen, C ₁ ~ C ₄₀ alkyl group, are selected from the group consisting of C ₆ ~ C ₆₀ aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group for, when the R ₅ a plurality individual, a plurality of R ₅ Are the same or different from each other;

The alkyl group, aryl group and heteroaryl group of R ₅ are each independently C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ Aryl group, When substituted or unsubstituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups having 5 to 60 nuclear atoms, and arylamine groups having ₆ to C ₆₀ atoms, they may be the same or different from each other. Can be.

According to one preferred embodiment of the invention, Ar ₁ and Ar ₂ may each independently be a substituent represented by any one of the following C1 to C58:

In the above C1 to C58, * means a portion where a bond is made.

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 by a synthetic method represented by Scheme 1 below, but is not limited thereto and may be synthesized by 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.

Scheme 1

In Scheme 1,

Y ₁ , Y ₂ and Y ₃ may be each independently selected from the group consisting of hydrogen, Cl and Br,

R ₃ , R ₄ , L, n, Ar ₁ and Ar ₂ are each as defined in Chemical Formulas 1 and 2 above.

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.

In the present invention, the compound represented by Chemical Formula 1 is basically excellent in electrochemical stability, high glass transition temperature and carrier transport ability, and electron mobility is also very excellent, showing the characteristics of blue emission efficiency is increased. The materials represented by Chemical Formula 1 are structurally characterized by combining a core core and an electron-withdrawing group (EWG), and are particularly excellent in electron mobility and excellent in high glass transition temperature and thermal stability. Therefore, the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer, an electron transport layer or an electron transport auxiliary layer.

According to the exemplary embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the 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 the compound represented by the formula (1), preferably the light emitting layer, electron transport layer or electron The transport auxiliary 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  1] 2- Bromo - Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

<Step 1> [(2- Pyridinylamino ) Thioxomethyl ]-, Of ethyl ester (9CI)  synthesis

To 100 g (1.06 mol) of 2-aminopyridine was added 500 mL of dichloromethane. Cool to 0 ° C. and 139.3 g (1.06 mol) of ethoxycarbonyl isocyanate were slowly added dropwise over 15 minutes. The reaction solution was raised to room temperature and stirred for 20 hours. After distillation under reduced pressure, the solvent was properly removed and filtered. After hot air drying, the desired compound 215 g (yield 90%) was obtained.

<Step 2> [1,2,4] triazolo [1,5-a] pyridine -2- Amine  synthesis

To 298 g (4.29 mol) of hydroxylamine hydrochloride was added an EtOH / MeOH (1: 1, 2.15 L) mixed solvent. 399 mL (2.86 mol) of triethylamine were added to the reaction solution, and the mixture was stirred for 1 hour. 215 g (0.95 mol) of [(2-pyridinylamino) thioxomethyl]-and ethyl ester (9CI) were added, and the temperature was gradually raised to reflux for 3 hours. The temperature was cooled to room temperature and the resulting solid was filtered off. The obtained solid product was combined, washed with purified water, EtOH / MeOH mixed solvent and n-hexane, followed by drying with air to obtain 115 g (yield 90%) of the title compound.

¹ H-NMR (in DMSO): δ 8.50 (dd, 1H), 7.39 (t, 1H), 7.29 (dd, 1H), 6.81 (t, 1H), 5.97 (s, 2H)

[LCMS]: 134

<Step 3> 2- Bromo - Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

57.5 g (0.26 mol) of CuBr ₂ and 1.2 L of THF were added to 115 g (0.86 mol) of [1,2,4] triazolo [1,5-a] pyridin-2-amine. The reaction solution was cooled to 0 ° C., 1.2 L of HBr was slowly added, and 177 g (2.57 mol) of NaNO ₂ was slowly added dropwise into 600 mL of purified water. The reaction solution was stirred at room temperature for 12 hours. 500 mL of an aqueous sodium hydroxide solution was added to the reaction solution, and after stirring for 1 hour, the mixture was extracted with EA 2 L and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 102 g (yield 60%) of the title compound.

¹ H-NMR (in DMSO): δ 8.92 (dd, 1H), 7.78 (dd, 1H), 7.72 (td, 1H), 7.23 (td, 1H)

[LCMS]: 198

[ Preparation  2] 2- Bromo -8-phenyl- Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

<Step 1> N-[[(3- Bromo -2- Pyridinyl ) Amino] Thioxomethyl ]-, Ethyl ester  synthesis

Except for using 2-amino-3-bromopyridine as a reaction, the same procedure as in Step 1 of [Preparation Example 1] was performed, to obtain 32 g (yield 88%) of the title compound.

<Step 2> 8- Bromo - [1,2,4] triazolo [1,5-a] pyridine -2- Amine  synthesis

Except for using N-[[(3-bromo-2-pyridinyl) amino] thioxomethyl]-and ethyl ester as reactants, target compound 20.2 was carried out in the same manner as in Step 2 of [Preparation Example 1]. g (yield 90%) was obtained.

¹ H-NMR (300Mz, CDCl ₃ ): δ 8.54 (d, 1H), 7.69 (d, 1H), 6.77 (t, 1H), 6.22 (s, 2H)

[LCMS]: 213

<Step 3> 2- Bromo - Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

To 20 g (93.9 mmol) of 8-bromo- [1,2,4] triazolo [1,5-a] pyridin-2-amine and 13.7 g (113 mmol) of phenylboronic acid, 300 mL of dioxane, H 100 mL of ₂ O was added. 5.4 g (4.7 mmol) of Pd (PPh ₃ ) _{4 and} 38.9 g (282 mmol) of K ₂ CO ₃ were added thereto, and the mixture was heated and refluxed at 120 ° C. for 3 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 16.8 g (yield 85%) of the title compound.

[LCMS]: 210

<Step 4> 2- Bromo -8-phenyl- Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

14.2 g (yield) of the target compound was obtained in the same manner as in Step 3 of [Preparation Example 1], except that 2-bromo- [1,2,4] triazolo [1,5-a] pyridine was used as the reactant. 65%).

¹ H-NMR (in DMSO): δ 8.92 (dd, 1H), 8.02 (m, 2H), 7.96 (dd, 1H), 7.52 (t, 2H), 7.46 (d, 1H), 7.33 (t, 1H )

[LCMS]: 274

[ Preparation  3] 2- Bromo -6-phenyl- Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

Except that 2-amino-5-bromopyridine was used as a reaction, the same procedure of Steps 1 to 4 of [Preparation Example 2] was performed, to obtain 10.5 g (yield 38%) of the title compound.

[LCMS]: 274

[ Preparation  4] 2- Bromo -6,8-diphenyl- Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

<Step 1> [ [(3,5- Dichloro -2- Pyridinyl ) Amino] Thioxomethyl ]-, Ethyl ester  Synthesis of (9CI)

48 g (yield 92%) of the title compound was obtained by the same procedure as in Step 1 of [Preparation Example 1], except that 2-amino-3,5-dichloropyridine was used as a reaction.

<Step 2> 6,8- Dichloro - [1,2,4] triazolo [1,5-a] pyridine -2- Amine  synthesis

Except for using [[(3,5-dichloro-2-pyridinyl) amino] thioxomethyl]-and ethyl ester (9CI) as reactants, the same procedure as in Step 2 of [Preparation Example 1] was carried out. 29.8 g (90% yield) of compound were obtained.

¹ H-NMR (300Mz, DMSO): δ 8.88 (s, 1H), 7.77 (s, 1H), 6.36 (s, 2H)

[LCMS]: 203

<Step 3> 6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine -2- Amine  synthesis

In 29 g (0.14 mol) of 6,8-dichloro- [1,2,4] triazolo [1,5-a] pyridin-2-amine and 41.8 g (0.34 mol) of phenylboronic acid, 400 mL of dioxane, H ₂ O was added to 150 mL. 3.2 g (0.014 mol) of Pd (OAc) ₂ , 13.6 g (0.0.09 mol) of XPhos, and 140 g (0.43 mol) of Cs ₂ CO ₃ were added and heated to reflux at 120 ° C. for 3 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of purified water. The mixture was extracted with 1 L of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 35.6 g (yield 87%) of the title compound.

¹ H-NMR (300Mz, CDCl ₃ ): δ 8.49 (d, 1H), 7.95 (d, 2H), 7.76 (d, 1H), 7.59 (d, 2H), 7.49 (m, 4H), 7.42 (t , 2H), 4.60 (s, 2H)

[LCMS]: 286

<Step 4> 2- Bromo -6,8-diphenyl- Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

Except for using 6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridin-2-amine as a reaction, the same procedure as in Step 3 of [Preparation Example 1] was performed. 22.3 g (52% yield) of the title compound were obtained.

¹ H-NMR (300Mz, CDCl ₃ ): δ 8.66 (d, 1H), 8.00 (dd, 2H), 7.92 (d, 1H), 7.60 (d, 2H), 7.52 (m, 4H), 7.46 (d , 2H)

[LCMS]: 350

[ Preparation  5] 2- Bromo Synthesis of -6,8-di (naphthalen-1-yl)-[1,2,4] triazolo [1,5-a] pyridine

Except that 2-amino-3,5-dichloropyridine and [1,1'-biphenyl] -4-ylboronic acid were used as reactants, the same procedure as in Steps 1 to 4 of [Preparation Example 4] was performed. 9.5 g (yield 28%) of the title compound were obtained.

[LCMS]: 502

[ Preparation  6] 2- Bromo Synthesis of -6,8-di (naphthalen-2-yl)-[1,2,4] triazolo [1,5-a] pyridine

Except for using 2-amino-3,5-dichloropyridine and naphthalen-2-ylboronic acid as the reaction product, the same procedure as in Steps 1 to 4 of [Preparation Example 4] was carried out to give 16.4 g of the target compound (yield 28% )

¹ H-NMR (in DMSO): δ 9.07 (s, 1H), 8.79 (s, 1H), 8.44 (s, 1H), 8.33 (dd, 1H), 8.27 (s, 1H), 8.00 (m, 5H ), 7.94 (m, 2H), 7.54 (m, 4H)

[LCMS]: 450

[ Preparation  7] 2- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran 2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine

<Step 1> 2 -(4- Chlorophenyl )- Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

Step of [Preparation Example 2], except that 2-bromo- [1,2,4] triazolo [1,5-a] pyridine and (4-chlorophenyl) boronic acid of Preparation Example 1 were used as reactants. 9.6 g (yield 82%) of the title compound was obtained by the same procedure as in 3.

[LCMS]: 229

<Step 2> 2- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran -2-yl) phenyl)- Of [1,2,4] triazolo [1,5-a] pyridine  synthesis

9.6 g (41.8 mmol) of 2- (4-chlorophenyl)-[1,2,4] triazolo [1,5-a] pyridine, 4,4,4 ', 4', 5,5 200 mL of dioxane was added to 12.7 g (50.2 mmol) of 5 ', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane). 1.7 g (2.1 mmol) of Pd (dppf) Cl ₂ and 12.3 g (125 mmol) of KOAc were added to the reaction solution. The mixture was heated to reflux at 130 ° C. for 6 hours. After cooling to room temperature, the reaction was terminated with 300 mL of aqueous ammonium chloride solution. The mixture was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 11.1 g (yield 83%) of the title compound.

[LCMS]: 321

[ Preparation  8] 2- (3- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran 2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine

Step of [Preparation Example 7], except that 2-bromo- [1,2,4] triazolo [1,5-a] pyridine and (3-chlorophenyl) boronic acid of Preparation Example 1 were used as reactants. 7.2 g (yield 40%) of the title compound were obtained by the same procedure as in 1-2.

[LCMS]: 321

[ Preparation  9] 8-phenyl-2- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran 2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine

Preparation Example 2, except that 2-bromo-8-phenyl- [1,2,4] triazolo [1,5-a] pyridine and (4-chlorophenyl) boronic acid of Preparation Example 2 were used as reactants. 7] was carried out in the same process as in Step 1 to 2 to obtain 10.5 g (yield 58%) of the title compound.

[LCMS]: 397

[ Preparation  10] Synthesis of diphenyl (6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-2-yl) phosphineoxide

<Step 1> of (6-bromonaphthalen-2-yl) diphenylphosphine oxide  synthesis

500 mL of toluene was added to 25 g (0.124 mol) of diphenylphosphine oxide and 82.3 g (0.247 mol) of 2-bromo-6-iodine naphthalene. 7.1 g (6.2 mmol) of Pd (PPh ₃ ) ₄ and 51.7 mL (0.371 mol) of TEA were added and heated to reflux at 120 ° C. for 6 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 24.2 g (yield 48%) of the title compound.

[LCMS]: 407

<Step 2> Synthesis of diphenyl (6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-2-yl) phosphine oxide

24 g of (6-bromonaphthalen-2-yl) diphenylphosphine oxide synthesized above was subjected to the same procedure as in Step 2 of [Preparation Example 7], except that 14.2 g of a target compound (yield 43 %) Was obtained.

[LCMS]: 454

[ Preparation  11] Synthesis of diphenyl (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-1-yl) phosphine oxide

9.4 g (yield 55%) of the title compound was obtained by the same procedure as in Steps 1 and 2 of [Preparation Example 10], except that diphenylphosphine oxide and 1-bromo-4-iodonaphthalene were used as reactants. .

[LCMS]: 454

[ Preparation  12] 6-phenyl-2- (3- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran 2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine

Preparation Example 3 except that 2-bromo-6-phenyl- [1,2,4] triazolo [1,5-a] pyridine and (3-chlorophenyl) boronic acid of Preparation Example 3 were used as reactants. 7.8 g (yield 48%) of the title compound were obtained by the same procedure as in Steps 1 and 2 of 7].

[LCMS]: 397

[ Preparation  13] 6,8-diphenyl-2- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboloran 2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine

Except for using 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and (4-chlorophenyl) boronic acid of Preparation Example 4 as reactants. 6.2 g (yield 49%) of the title compound were obtained by the same procedure as in Steps 1 and 2 of [Preparation Example 7].

¹ H-NMR (300Mz, CDCl ₃ ): δ 8.76 (s, 1H), 8.34 (d, 2H), 8.18 (d, 2H), 7.92 (d, 2H), 7.90 (s, 1H), 7.64 (d , 2H), 7.52 (m, 6H)

[LCMS]: 473

[ Preparation  14] 6,8-di ([1,1'-biphenyl] -4-yl) -2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaboro Synthesis of lan-2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine

6,8-di ([1,1'-biphenyl] -4-yl) -2-bromo- [1,2,4] triazolo [1,5-a] pyridine of Preparation Example 5 as a reaction product; Except for using (4-chlorophenyl) boronic acid was carried out the same procedure as in Step 1 to 2 of [Preparation Example 7] to obtain 6.2 g (yield 49%) of the target compound.

[LCMS]: 625

[ Preparation  15] 6,8-di (naphthalen-2-yl) -2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -Synthesis of [1,2,4] triazolo [1,5-a] pyridine

2-Bromo-6,8-di (naphthalen-2-yl)-[1,2,4] triazolo [1,5-a] pyridine and (4-chlorophenyl) boronic acid of Preparation Example 6 as reactants Except for using the same procedure as in Steps 1 and 2 of [Preparation Example 7] to give the target compound 11.4 g (56% yield).

[LCMS]: 573

[ Synthesis Example  1] Synthesis of Compound 2

[Preparation Example] Except that 2-bromo- [1,2,4] triazolo [1,5-a] pyridine and (4-bromophenyl) diphenylphosphine oxide of Preparation Example 1 were used as reactants. 2] was carried out in the same manner as in Step 3, to obtain 5.5 g (yield 38%) of the title compound.

[LCMS]: 395

[ Synthesis Example  2] Synthesis of Compound 3

Preparation of reactants 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,2,4] tria of Preparation Example 7 3.7 g of the target compound (yield 44%) were carried out in the same manner as in Step 3 of [Preparation Example 2], except that zolo [1,5-a] pyridine and (4-bromophenyl) diphenylphosphineoxide were used. )

[LCMS]: 471

[ Synthesis Example  3] Synthesis of Compound 6

Preparation of reactants 2- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,2,4] tria of Preparation Example 8 Except for using zolo [1,5-a] pyridine and (3-bromophenyl) diphenylphosphine oxide, the same procedure as in Step 3 of [Preparation Example 2] was performed, to obtain 5.5 g of the target compound (yield 39%). )

[LCMS]: 471

[ Synthesis Example  4] Synthesis of Compound 10

Preparation of reactants 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,2,4] tria of Preparation Example 7 The same procedure as in Step 3 of [Preparation Example 2] was performed except that zolo [1,5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphine oxide) were used. To give 5.4 g (yield 47%) of the title compound.

[LCMS]: 671

[ Synthesis Example  5] Synthesis of Compound 15

Preparation as reactant 8-phenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,2 , 4] Triazolo [1,5-a] pyridine and (3-bromophenyl) diphenylphosphine oxide were used to carry out the same procedure as in Step 3 of [Preparation Example 2], to give 3.2 g of the target compound. (Yield 58%) was obtained.

[LCMS]: 547

[ Synthesis Example  6] Synthesis of Compound 19

2-Bromo-8-phenyl- [1,2,4] triazolo [1,5-a] pyridine of Preparation Example 2 and diphenyl (6- (4,4,5,5) of Preparation Example 10 as a reactant Tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-2-yl) phosphine oxide was used to carry out the same procedure as in Step 3 of [Preparation Example 2], except that 6.2 g (yield 55%) of compound were obtained.

[LCMS]: 521

[ Synthesis Example  7] Synthesis of Compound 21

Preparation as reactant 8-phenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,2 Step 3 of [Preparation Example 2], except that triazolo [1,5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphine oxide) were used; The same procedure was followed to obtain 2.9 g (yield 60%) of the title compound.

[LCMS]: 747

[ Synthesis Example  8] Synthesis of Compound 29

2-Bromo-6-phenyl- [1,2,4] triazolo [1,5-a] pyridine of Preparation Example 3 and diphenyl (4- (4,4,5,5) of Preparation Example 11 as a reactant. Tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-1-yl) phosphine oxide was used to carry out the same procedure as in Step 3 of [Preparation Example 2], except that 4.3 g (37% yield) of compound was obtained.

[LCMS]: 521

[ Synthesis Example  9] Synthesis of Compound 33

Preparation as reactant 6-phenyl-2- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,2 Step 3 of [Preparation Example 2], except that triazolo [1,5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphine oxide) were used. The same procedure was followed to obtain 2.5 g (yield 60%) of the title compound.

[LCMS]: 747

[ Synthesis Example  10] Synthesis of Compound 36

Preparation as reactant 6,8-diphenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) of Preparation Example 13- [ The same procedure as in Step 3 of [Preparation Example 2] was carried out except that 1,2,4] triazolo [1,5-a] pyridine and (4-bromophenyl) diphenylphosphine oxide were used. 5.7 g (52% yield) of compound were obtained.

¹ H-NMR (300Mz, CDCl ₃ ): δ 8.77 (d, 1H), 8.43 (d, 2H), 8.20 (d, 2H), 7.91 (d, 1H), 7.76 (m, 8H), 7.68 (dd , 2H), 7.64 (dd, 2H), 7.55 (m, 6H), 7.46 (m, 6H)

[LCMS]: 623

[ Synthesis Example  11] Synthesis of Compound 37

Preparation as reactant 6,8-diphenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) of Preparation Example 13- [ The same procedure as in Step 3 of [Preparation Example 2] was carried out except that 1,2,4] triazolo [1,5-a] pyridine and (3-bromophenyl) ylphenylphosphine oxide were used. 3.4 g (54% yield) of compound was obtained.

¹ H-NMR (300Mz, CDCl ₃ ): δ 8.78 (d, 1H), 8.39 (d, 2H), 8.19 (d, 2H), 8.03 (d, 1H), 7.91 (d, 1H), 7.84 (d , 1H), 7.72 (t, 3H), 7.69 (m, 5H), 7.56 (m, 7H), 7.46 (m, 7H)

[LCMS]: 623

[ Synthesis Example  12] Synthesis of Compound 43

Preparation as reactant 6,8-diphenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) of Preparation Example 13- [ Preparation of 2, except that 1,2,4] triazolo [1,5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphineoxide) were used 7.3 g (yield 45%) of the title compound were obtained by the same procedure as in Step 3.

[LCMS]: 823

[ Synthesis Example  13] Synthesis of Compound 47

Preparation as reactant 6,8-di ([1,1'-biphenyl] -4-yl) -2- (4- (4,4,5,5-tetramethyl-1,3,2- in Example 14 Except that dioxaborolan-2-yl) phenyl)-[1,2,4] triazolo [1,5-a] pyridine and (4-bromophenyl) diphenylphosphineoxide were used Preparation Example 2] was carried out in the same manner as in Step 3 to obtain 3.3 g (yield 40%) of the title compound.

[LCMS]: 775

[ Synthesis Example  14] Synthesis of Compound 51

6,8-di ([1,1'-biphenyl] -4-yl) -2-bromo- [1,2,4] triazolo [1,5-a] pyridine of Preparation Example 5 as a reaction product; Except for using the diphenyl (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-1-yl) phosphine oxide of Preparation Example 11 Then, the same procedure as in Step 3 of [Preparation Example 2], to obtain 5.3 g (yield 41%) of the title compound.

[LCMS]: 749

[ Synthesis Example  15] Synthesis of Compound 59

Preparation as reactant 6,8-di (naphthalen-2-yl) -2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- in Preparation Example 15 Step 3 of [Preparation Example 2] except that 1) phenyl)-[1,2,4] triazolo [1,5-a] pyridine and (3-bromophenyl) ylphenylphosphine oxide were used. The same procedure was followed to obtain 2.5 g (yield 40%) of the title compound.

[LCMS]: 723

[ Synthesis Example  16] Synthesis of Compound 62

2-Bromo-6,8-di (naphthalen-2-yl)-[1,2,4] triazolo [1,5-a] pyridine of Preparation Example 6 and diphenyl (4) of Preparation Example 11 [Preparation Example 2], except that (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-1-yl) phosphine oxide was used. The same procedure as in Step 3 was carried out to obtain 5.5 g (yield 35%) of the title compound.

[LCMS]: 697

[ Synthesis Example  17] Synthesis of Compound 64

Preparation as reactant 6,8-di (naphthalen-2-yl) -2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- in Preparation Example 15 (L) phenyl)-[1,2,4] triazolo [1,5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphineoxide) except that 4.0 g (yield 49%) of the title compound was obtained by the same procedure as in Step 3 of [Preparation Example 2].

[LCMS]: 923

[ Example  1 to 13] blue organic Electric field  Fabrication of light emitting device

Compounds 2, 3, 10, 19, 21, 29, 36, 37, 43, 47, 51, 62, and 64 synthesized in Synthesis Example were subjected to high purity sublimation purification by a conventionally known method, followed by a blue organic electric field as follows. A light emitting 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 ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30nm) / Compound 2, 3, 10, 19 , 21, 29, 36, 37, 43, 47, 51, 62, 64 each compound (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.

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

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq ₃ was used instead of the compound 2 as the electron transporting layer material.

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

A blue organic EL device was manufactured in the same manner as in Example 1, except that Compound 2 was not used as the electron transporting material.

The structures of NPB, AND, and Alq3 used in Examples 1 to 13 and Comparative Examples 1 and 2 are as follows.

[Evaluation Example 1]

For the blue organic electroluminescent devices fabricated in Examples 1 to 13 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 2 3.8 452 7.5 Example 2 Compound 3 4.2 452 8.0 Example 3 Compound 10 3.6 453 7.8 Example 4 Compound 19 3.3 452 8.2 Example 5 Compound 21 3.8 453 8.0 Example 6 Compound 29 4.1 452 7.8 Example 7 Compound 36 3.9 455 8.4 Example 8 Compound 37 3.6 450 8.5 Example 9 Compound 43 3.3 452 7.7 Example 10 Compound 47 3.6 453 7.9 Example 11 Compound 51 3.9 450 8.3 Example 12 Compound 62 4.0 454 7.9 Example 13 Compound 64 3.9 452 8.1 Comparative Example 1 Alq ₃ 5.4 458 5.5 Comparative Example 2 - 4.9 460 5.8

As shown in Table 1, the blue organic electroluminescent devices (Examples 1 to 13) using the compound of the present invention in the electron transporting layer were prepared using a blue organic electroluminescent device (comparative example 1) using Alq ₃ as the electron transporting layer. 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.

Examples 14 to 23 Fabrication of Blue Organic Electroluminescent Devices

Compounds 3, 6, 15, 21, 33, 37, 51, 59, 62, and 64 synthesized in Synthesis Example were subjected to high purity sublimation purification using a conventionally known method. It was.

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, 30nm) / Compound 20, 25, 83, 95 , 107, 110, 123, 131, 144, 153 (5 nm) / Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to prepare an organic EL device.

Comparative Example 3 Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 12, except that Compound 3 was not used as the electron transport auxiliary layer material, and Alq ₃ , which is an electron transport layer material, was deposited at 30 nm instead of 25 nm. .

*

[Evaluation Example 2]

For the organic electroluminescent devices manufactured in Examples 14 to 23 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 14 Compound 3 4.4 456 8.7 Example 15 Compound 6 3.3 450 8.5 Example 16 Compound 15 3.7 452 9.0 Example 17 Compound 21 3.8 455 8.2 Example 18 Compound 33 3.6 458 7.9 Example 19 Compound 37 3.9 458 8.5 Example 20 Compound 51 3.5 450 8.8 Example 21 Compound 59 4.1 452 8.5 Example 22 Compound 62 3.7 455 7.5 Example 23 Compound 64 3.8 456 8.4 Comparative Example 3 - 4.8 458 6.0

As shown in Table 2, the blue organic electroluminescent devices (Examples 14 to 23) 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, light 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 (13)

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

In Chemical Formula 1, Z ₁ to Z ₃ are respectively and independently N or C (R _2), at least two of the Z ₁ to Z ₃ are N; m is an integer from 0 to 4; 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 ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl 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 is selected from diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of, when the plurality of R ₁ individual, a plurality of R ₁ are the same or different from each other; L is selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms; R ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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; Arylene group and a heteroarylene group, an alkyl group of said R ₁ and R ₂ of the L, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl The group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, aryl phosphinyl group and aryl amine 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 ~ 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 alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When unsubstituted or substituted with one or more substituents selected from the group consisting of, these are the same or different from each other; D is a substituent represented by the following formula (2); n is an integer of 1 or 2, and when n is 2, the two Ds are the same or different from each other; [Formula 2]

In Chemical Formula 2, * Means the part where the bond is made; Ar ₁ and Ar ₂ 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 ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the; Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl of Ar ₁ and Ar ₂ boron group, an aryl phosphazene group, an aryl Phosphinicosuccinic group and aryl amine groups are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of Substituted with ventilation or unsubstituted and, if substituted with a plurality of substituents, they are same as or different from each other. The method of claim 1, The compound is a compound represented by the formula [Formula 3]

In Chemical Formula 3, R ₃ and R ₄ are each independently hydrogen, deuterium, an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C ₆ to C ₆₀ Selected from the group consisting of, R ₃ and R ₄ are not all hydrogen; The alkyl group, aryl group, heteroaryl group and arylamine group of R ₃ and R ₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C Or substituted with one or more substituents selected from the group consisting of ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, and C ₆ to C ₆₀ arylamine groups Ring, and when substituted with a plurality of substituents, they may be the same or different from each other, Z ₁ to Z ₃ , L, D and n are each as defined in claim 1. The method of claim 1, The compound is a compound represented by the following formula (4): [Formula 4]

In Chemical Formula 4, R ₁ , L, D, m and n are each as defined in claim 1. The method of claim 1, R ₁ is selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, a phenanthrenyl group, and a triphenylenyl group. The method of claim 2, At least one of the R ₃ and R ₄ is selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, phenanthrenyl group and triphenylenyl group. The method of claim 1, Wherein L is a linker represented by Formula 5 below: [Formula 5]

In Chemical Formula 5, * Means the part where the bond is made; L ₁ to L ₃ may be each independently selected from the group consisting of a single bond, a phenylene group, a pyridinyl group, and a naphthalenyl group. The method of claim 1, When n is 1, L is a linker selected from the group consisting of A1 to A5, wherein:

In A1 to A5, * Means the part where the coupling is made. The method of claim 1, When n is 2, L is a linker selected from the group consisting of B1 to B4,

In the B1 to B4, * Means the part where the coupling is made. The method of claim 1, Ar ₁ and Ar ₂ are each independently a substituent represented by formula (6): [Formula 6]

In Chemical Formula 6, * Means the part where the bond is made; X ₁ to X ₅ are each independently N or C (R ₅ ); R ₅ is hydrogen, C ₁ ~ C ₄₀ alkyl group, are selected from the group consisting of C ₆ ~ C ₆₀ aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group for, when the R ₅ a plurality individual, a plurality of R ₅ Are the same or different from each other; The alkyl group, aryl group and heteroaryl group of R ₅ are each independently C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ Aryl group, When substituted or unsubstituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups having 5 to 60 nuclear atoms, and arylamine groups having ₆ to C ₆₀ atoms, they may be the same or different from each other. Can be. The method of claim 1, Ar ₁ and Ar ₂ are each independently a substituent represented by any one of the following C1 to C58:

In the C1 to C58, * Means the part where the coupling is made. The method of claim 1, Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of:

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 12, 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.