KR20150098977A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel phenazine-based compound with excellent hole injection, hole transfer, and light emitting properties, and to an organic electroluminescent device including the phenazine-based compound in an organic layer to improve characteristics such as light emitting efficiency, a driving voltage, lifespan, etc.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound and an organic electroluminescent device including the same.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material contained in the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, or the like depending on its function.

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

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the phosphorescent dopant can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent dopant, studies on the phosphorescent dopant as well as the phosphorescent host have been conducted.

Currently, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. As phosphorescent dopant materials used for the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like are known. As phosphorescent host materials, 4,4-dicarbazolybiphenyl (CBP) is known.

However, existing materials have advantages in terms of luminescent properties, but their thermal stability is poor due to their low glass transition temperature, which is not satisfactory in terms of lifetime of an organic electroluminescent device.

Korea public patent 2011-0066763

It is an object of the present invention to provide a novel organic compound having a high glass transition temperature and excellent thermal stability.

It is another object of the present invention to provide an organic electroluminescent device comprising the organic compound.

The present invention provides a compound represented by the following formula (1).

In Formula 1,

X ₁ and X ₂ are the same as or different from each other, and each independently C (R ₈ ) or N, where R ₈ is plural, they are the same or different from each other;

One of R ₁ to R ₈ is bonded to an adjacent group to form a condensed ring represented by the following formula (2);

In the formula (2), the dotted line represents a moiety which is condensed with the formula (1)

Y ₁ and Y ₂ are the same or different, each independently represent _{N (Ar 1), O,} S, C (Ar 2) (Ar 3) and Si (Ar ₄₎ is selected from the group consisting of (Ar ₅₎ , Provided that at least one of Y ₁ and Y ₂ is N (Ar ₁ ), provided that when Ar ₁ is plural, they are the same as or different from each other;

Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, A heterocyclic alkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group , is selected from the aryl phosphine oxide group, and the group consisting of a C ₆ ~ C ₄₀ aryl silyl group of C ₆ ~ C _40,

The general formula (2) condensation of R ₁ to not form a ring of the R ₈ and R ₉ to R ₁₂ are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group to each other, C ₁ ~ C _A C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group , A heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of the An arylamine group, or may be bonded to an adjacent group to form a condensed ring,

The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the aryl group of the R ₁ to R ₁₂ and Ar ₁ to Ar ₅ The silyl group, the alkyl boron group, the aryl boron group, the aryl phosphine group, the aryl phosphine oxide group and the arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ or aryl amines When substituted, and, just in the plurality is a substituent, they may be the same or different from each other.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound And an organic electroluminescent device.

Here, the one or more organic layers include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one of them, preferably a light emitting layer, is represented by the above-mentioned formula (1). In particular, in the light emitting layer, the compound represented by Formula 1 is a phosphorescent host.

The compound represented by the general formula (1) of the present invention is excellent in thermal stability and luminescent properties and can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host, it is possible to manufacture an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, and long life time as compared with a conventional host, A full color display panel having an improved life span can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The compound of the present invention can be produced by reacting a phenazine-based moiety at the terminal of a condensed heterocyclic moiety formed by condensation of a nitrogen-containing, membered heteroaromatic ring (such as pyrrole, imidazole, pyrazole, triazole) , And aromatic rings such as indole, benzothiophene, benzofuran, benzoyl, and heteroaromatic rings are condensed to form a basic skeleton, and various substituents are bonded to the basic skeleton.

The compound represented by Formula 1 can be applied to the hole injecting layer and the hole transporting layer because the phenazine moiety in the basic skeleton has excellent hole transportability. Since various aromatic ring substituents, particularly substituents having excellent electron transporting properties, are introduced into such a basic skeleton, the compounds of the present invention are excellent in electron withdrawing group (EWG) Electron donating group (EDG), so it becomes bipolar. As a result, the compound of the present invention has a high bonding force between holes and electrons, and thus can be advantageously applied as a host in a phosphorescent light-emitting layer.

In addition, the compound of the present invention may have various substituents bonded to the condensed heterocyclic moiety in the basic skeleton or may be condensed with an aromatic ring or a heteroaromatic ring at the end of the condensed heterocyclic moiety, Temperature, which is superior in thermal stability to the conventional organic material layer (for example, CBP).

Accordingly, when the compound of Formula 1 according to the present invention is used as an organic material layer material (preferably a material of the light emitting layer) of an organic electroluminescent device, the durability, efficiency and lifetime of the organic electroluminescent device can be improved as compared with the conventional organic material layer material . In addition, the lifetime of the organic electroluminescent device can be maximized to maximize the performance of the full color organic electroluminescent panel.

In the compound of formula (I) according to the present invention, X ₁ and X ₂ are the same or different and each independently C (R ₈ ) or N, provided that when R ₈ is plural, they are the same as or different from each other.

Preferably, when one of X ₁ and X ₂ is C (R ₈ ) and the remainder is N, and more preferably, when X ₁ and X ₂ are both C (R ₈ ), the luminescent property of the organic electroluminescent device is Can be improved. Here, when a plurality of R < ₈ > are plural, they are the same or different from each other.

In addition, one of R ₁ to R ₈ is bonded to an adjacent group to form a condensed ring represented by the above formula (2).

Preferably, any one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , and R ₆ and R ₇ are bonded to each other to form a condensed ring represented by Formula 2 .

In one example, R ₁ and R _2, R ₂ and R _3, R ₃ and R _4, R ₅ and R _6, R ₆ and R ₇ in R ₁ and R ₂ is a condensed ring represented by the above formula (2) bonded to each other , The compound may be represented by the following general formula (3) or (4).

As another example, R ₁ and R _2, R ₂ and R _3, R ₃ and R _4, R ₅ and R _6, R ₆ and R ₇ fused displayed in combination to each other the R ₂ and R ₃ in the general formula (2) When a ring is formed, the compound may be represented by the following formula (5) or (6).

In another example, R ₁ and R _2, R ₂ and R _3, R ₃ and R _4, R ₅ and R _6, R ₆ and R ₇ in R ₃ and the R ₄ are bonded to each other represented by the above formula (2) When the condensed ring is formed, the compound may be represented by the following general formula (7) or (8).

In the above Formulas 3 to 8,

X ₁ , X ₂ , Y ₁ , Y _2, and R ₁ to R ₁₂ are the same as defined in Formula 1, respectively.

In the above formula (2), the dotted line is a moiety which is condensed with the formula (1).

Further, Y ₁ and Y ₂ are the same or different, each independently from the group consisting of _{N (Ar 1), O,} S, C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) With the proviso that at least one of Y ₁ and Y ₂ is N (Ar ₁ ). At this time, when a plurality of Ar < _{1 >} are present, they are the same as or different from each other.

Preferably, Y ₁ and Y ₂ are the same or different and each independently selected from the group consisting of N (Ar ₁ ), O and S, wherein when Ar ₁ is plural, they are the same or different from each other.

More preferably, Y ₁ and Y ₂ may all be N (Ar ₁ ). At this time, a plurality of Ar < ₁ > s are the same or different from each other.

In the formula (1), in consideration of the broad bandgap and thermal stability of the compound, Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₆ to C ₆₀ aryl group, a hetero atom having 5 to 60 nuclear atoms An aryl group and an arylamine group of C ₆ to C ₄₀ .

In this case, the alkyl group of said Ar ₁ to Ar _5, 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 group, an arylsilyl group, an alkyl boronic group , an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ substituted from the group consisting of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine, with one or more substituents selected or is unsubstituted. However, when there are a plurality of substituents, they may be the same or different.

R ₁ to R ₈ and R ₉ to R ₁₂ in which the condensed ring of Formula 2 is not mutually the same or different are each independently hydrogen, deuterium (D), halogen, cyano, C ₁ to C ₄₀ that of the alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms selected from the group consisting of a heteroaryl group of from 5 to 60, and C ₆ ~ C ₆₀ aryl amines are preferred.

The alkyl, aryl, heteroaryl and arylamine groups of R ₁ to R ₈ and R ₉ to R ₁₂ in which the condensed ring of Formula 2 is not formed are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ or an alkenyl group of C _40, C ₂ to C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 of to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ of the aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ of group of the C ₄₀ alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ Lt; RTI ID = 0.0 > 1, < / RTI > However, when there are a plurality of substituents, they may be the same or different.

More preferably, in the general formula (1), Ar ₁ to Ar ₅ and R ₁ to R ₈ and R ₉ to R ₁₂ in which the condensed ring of the general formula (2) is not formed are each independently hydrogen or a group consisting of the following substituents S1 to S205 ≪ / RTI >

Wherein at least one of R ₁ to R ₈ and R ₉ to R _{12 in} which Ar ₁ and the condensed ring of Formula 2 are not formed is a substituent represented by the following Formula 9, As defined.

In the above formula (9)

L is either a single bond or a C ₆ ~ C ₄₀ aryl group, and the number of nuclear atoms is selected from the group consisting of 5 to 40 hetero arylene group, and preferably is a single bond, phenylene, or biphenyl may and renil ;

Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₁₃ ), provided that at least one of Z ₁ to Z ₅ is N, and when R ₁₃ is plural, Z ₁ to Z ₅ are preferably at least one to three of N and the others are C (R ₁₃ ), and when R ₁₃ is plural, they are the same or different;

R ₁₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl group, and a phosphine oxide selected from the group consisting of C ₆ ~ C ₆₀ aryl group of an amine or of, or coupled to adjacent groups may form a condensed ring;

At this time, the arylene group and a heteroarylene group, an alkyl group of R _13, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group in the L, alkylsilyl group, The arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of C ₆₀ arylamine Provided that when the substituent is plural, they may be the same or different.

Preferably, at least one of R ₁ to R ₈ and R ₉ to R ₁₂ in which Ar ₁ and the condensed ring of Formula 2 are not formed is selected from the group consisting of substituents represented by the following Formulas A-1 to A-15 And the others are the same as defined in the above formula (1).

In the above formulas A-1 to A-15,

L And R < ₁₃ > are the same as defined in the above formula (9)

n is an integer from 0 to 4, n is 0, meaning that hydrogen is not substituted by substituents R _21, and n is an integer from 1 to 4, R ₂₁ is deuterium (D), a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ of the arylamine group, C ₁ ~ C ₄₀ groups of the alkyl silyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of C ₄₀ arylsilyl in combination, or the adjacent group to which they are attached may form a fused ring,

In this case, the alkyl group of said R _21, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group, and aryl Each of the amine groups is independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms , A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group , C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C of ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine An aryl group having 1 to ₆ carbon atoms, an aryl group having ₆ to ₂₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms, All.

Examples of the compound represented by the formula (1) include compounds represented by the following formulas (10) to (15), but are not limited thereto.

In the above formulas 10 to 15,

A plurality of Ar < _{1 >} may be the same or different from each other,

Ar ₁ and R ₁ to R ₁₂ are the same as defined in Formula 1, respectively.

The compounds of formula (I) according to the present invention can be exemplified by the following exemplified compounds, but are not limited thereto.

In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

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

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may 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 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and R represents aryl having 6 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

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

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.

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

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > 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 6 to 40 carbon atoms.

In the present invention, "alkylboron group" means a boron group substituted with alkyl having 1 to 40 carbon atoms, "arylboron group" means a boron group substituted with aryl having 6 to 60 carbon atoms, Means a phosphine group substituted with aryl of 1 to 60, and the term "arylphosphine oxide group" means a phosphine oxide group substituted with aryl having 1 to 60 carbon atoms.

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

The compounds of formula (1) according to the present invention can be synthesized in various ways with reference to the following synthesis examples.

2. Organic electroluminescent device

The present invention also provides an organic electroluminescent device comprising the compound represented by the above-mentioned formula (1).

More specifically, the present invention provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes an organic electric field A light emitting device is provided. At this time, the compound represented by the formula (1) may be used singly or in combination of two or more.

The at least one organic compound layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Preferably, the light-emitting layer may include a compound represented by the general formula (1). At this time, the compound represented by Formula 1 may be included in an organic electroluminescent device as a light emitting layer material, preferably a phosphorescent host, a fluorescent host or a dopant material, more preferably a phosphorescent host. In this case, the light emitting efficiency, brightness, power efficiency, thermal stability, and device lifetime of the organic electroluminescent device can be improved.

The structure of the organic electroluminescent device of the present invention is not particularly limited. For example, a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated on a substrate, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer .

Specifically, the organic electroluminescent device may have a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated on a substrate, and an electron injecting layer is selectively disposed between the electron transporting layer and the cathode can do. At this time, at least one of the hole injecting layer, the hole transporting layer and the light emitting layer may contain at least one compound represented by the above formula (1).

The organic electroluminescent device of the present invention can be manufactured by using materials and methods known in the art, except that at least one of the organic layers (for example, the light emitting layer) includes the compound represented by the above formula (1) ≪ / RTI >

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 examples thereof include silicon wafers, quartz or glass plates, metal plates, plastic films and sheets, and the like.

Examples of the positive electrode 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), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The material used for the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer is not particularly limited as long as it is a conventional material known in the art.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[ Preparation Example  One] IAC Synthesis of -1

<Step 1> Synthesis of IAC-1-1

(11.5 g, 69.0 mmol), 1-bromo-2-iodobenzene (19.5 g, 69.0 mmol), Cu powder (0.45 g, 6.90 mmol), K ₂ CO ₃ , 138.0 mmol), Na ₂ SO ₄ (19.5 g, 138.0 mmol), and nitrobenzene (250 ml) were mixed and stirred at 250 ° C for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water had been removed, the product was purified by column chromatography to obtain IAC-1-1 (13.8 g, yield 63%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.34 (t, 1H), 7.51 (m, 3H), 7.60 (m, 2H), 8.03 (d, 1H), 8.32 (d, 1H)

<Step 2> Synthesis of IAC-1-2

IAC-1-1 (6.34 g, 20.0 mmol), triphenylphosphine (15.7 g, 60.00 mmol) obtained in the above Step 1 and 1,2-dichlorobenzene (100 ml) were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed from the resulting organic layer with MgSO ₄ and purified by column chromatography to obtain IAC-1-2 (4.11 g, yield 72%).

^{1 H-NMR: δ 5.99 (} d, 1H), 6.13 (t, 1H), 6.51 (m, 2H), 6.93 (m, 2H), 7.21 (d, 1H), 7.59 (d, 1H), 9.92 ( s, 1 H)

<Step 3> Synthesis of IAC-1-3

(17.1 g, 60.0 mmol), 2-nitrophenylboronic acid (11.0 g, 66.0 mmol), NaOH (7.20 g, 180.0 mmol) and THF / H ₂ O a mixture of 80 ml / 40 ml) in the _{following, Pd (PPh 3) 4 (} 80 ℃ put 3.48 g, 5 mol%) was stirred for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography to obtain IAC-1-3 (14.1 g, yield 72%).

^{1 H-NMR: δ 5.98 (} d, 1H), 6.14 (t, 1H), 6.52 (m, 2H), 7.20 (m, 2H), 7.25 (d, 1H), 7.66 (m, 2H), 7.99 ( m, 3 H), 9.91 (s, 1 H)

<Step 4> Synthesis of IAC-1-4

(7.53 g, 23.0 mmol), iodobenzene (4.69 g, 23.0 mmol), Cu powder (0.15 g, 2.30 mmol) and K ₂ CO ₃ (6.3 g, 46.0 mmol) obtained in Step ₃ , , Na ₂ SO ₄ (6.5 g, 46.0 mmol) and nitrobenzene (100 ml) were mixed and stirred at 250 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed, and then purified by column chromatography to obtain IAC-1-4 (7.14 g, yield 77%).

^{1 H-NMR: δ 5.98 (} d, 1H), 6.15 (t, 1H), 6.52 (m, 4H), 6.81 (t, 1H), 7.23 (m, 4H), 7.44 (t, 1H), 7.66 ( m, 2 H), 8.01 (m, 3 H)

<Step 5> Synthesis of IAC-1

Step 2 of Preparation Example 1 was repeated except that IAC-1-4 (8.07 g, 20.0 mmol) was used instead of IAC-1-1 used in Step 2 to prepare IAC- 1 (4.90 g, yield 66%).

^{1 H-NMR: δ 5.94 (} d, 1H), 6.11 (t, 1H), 6.55 (m, 3H), 6.77 (m, 2H), 7.23 (m, 4H), 7.38 (d, 1H), 7.53 ( m, 3H), 8.12 (d, IH), 10.41 (s, IH)

[Preparation Example 2] Synthesis of IAC-2 and IAC-3

<Step 1> Synthesis of IAC-2-1

Except that 1-bromo-3-iodobenzene (19.5 g, 69.0 mmol) was used in place of 1-bromo-2-iodobenzene used in <Step 1> of Preparation Example 1, The same procedure was followed to obtain IAC-2-1 (16.0 g, yield 73%).

^{1 H-NMR: δ 6.55 (} d, 1H), 7.38 (m, 2H), 7.51 (t, 1H), 7.61 (m, 3H), 7.99 (d, 1H), 8.31 (d, 1H)

<Step 2> Synthesis of IAC-2-2 and IAC-4-2

The same procedure as in <Step 2> of Preparation Example 1 was carried out except that IAC-2-1 (8.07 g, 20.0 mmol) was used instead of IAC-1-1 used in <Step 2> of Preparation Example 1 To obtain IAC-2-2 (2.62 g, yield 46%) and IAC-4-2 (2.34 g, yield 41%).

¹ H-NMR of the IAC-2-2: δ 5.93 (d , 1H), 6.11 (t, 1H), 6.55 (m, 2H), 7.28 (d, 1H), 7.35 (m, 2H), 7.62 (d , &Lt; / RTI &gt; 1H), 9.41 (s, 1H)

IAC-4-2 ¹ H-NMR of: δ 5.93 (d, 1H) , 6.13 (t, 1H), 6.53 (d, 1H), 6.70 (t, 1H), 7.28 (m, 2H), 7.62 (m , 2H), 9.44 (s, 1 H)

<Step 3> IAC Synthesis of -2-3

Except that the IAC-2-2 (17.1 g, 60.0 mmol) obtained in the above Step 2 was used instead of the IAC-1-2 used in the <Step 3> of Preparation Example 1, 3 &gt;, IAC-2-3 (15.9 g, yield 81%) was obtained.

^{1 H-NMR: δ 5.93 (} d, 1H), 6.13 (t, 1H), 6.59 (m, 2H), 7.28 (d, 1H), 7.59 (m, 3H), 7.82 (s, 1H), 8.01 ( m, 3 H), 9.87 (s, 1 H)

<Step 4> Synthesis of IAC-2-4

Except that IAC-2-3 (7.53 g, 23.0 mmol) obtained in the above Step 3 was used instead of IAC-1-3 used in <Step 4> of Preparation Example 1, 4 &gt;, IAC-2-4 (6.59 g, yield 71%) was obtained.

^{1 H-NMR: δ 5.94 (} d, 1H), 6.13 (t, 1H), 6.52 (d, 1H), 6.63 (m, 3H), 7.20 (m, 2H), 7.28 (d, 1H), 7.59 ( m, 4H), 7.84 (s, IH), 8.01 (m, 3H)

<Step 5> Synthesis of IAC-2 and IAC-3

Except that IAC-2-4 (8.07 g, 20.0 mmol) obtained in the above <Step 4> was used instead of IAC-1-4 used in <Step 5> of Preparation Example 1, IAC-2 (3.12 g, yield 42%) and IAC-3 (3.08 g, yield 41%) were obtained by the same procedure as in Example 1,

¹ H-NMR of IAC-2:? 5.94 (d, IH), 6.13 (t, IH), 6.65 (m, 4H), 6.79 (t, ), 7.65 (m, 2H), 7.73 (s, IH), 8.12 (d, IH), 10.31

Of the ^{IAC-3 1 H-NMR:} δ 5.93 (d, 1H), 6.13 (t, 1H), 6.65 (m, 4H), 6.81 (t, 1H), 7.24 (m, 4H), 7.53 (m, 3H ), 7.65 (m, 3H), 8.09 (m, 2H), 10.31

[Preparation Example 3] Synthesis of IAC-4

<Step 1> Synthesis of IAC-4-3

Except that IAC-4-2 (17.1 g, 60.0 mmol) obtained in <Step 2> of Preparation Example 2 was used instead of IAC-1-2 used in <Step 3> of Preparation Example 1, (15.4 g, yield 80%) was obtained by carrying out the same procedure as in < Step 3 >.

^{1 H-NMR: δ 5.94 (} d, 1H), 6.13 (t, 1H), 6.52 (d, 1H), 6.87 (t, 1H), 7.29 (m, 2H), 7.58 (d, 1H), 7.69 ( m, 2 H), 7.90 (m, 3 H), 9.61 (s, 1 H)

<Step 2> Synthesis of IAC-4-4

Except that the IAC-4-3 (7.53 g, 23.0 mmol) obtained in the above Step 1 was used instead of the IAC-1-3 used in the <Step 4> of Preparation Example 1, 4 &gt; to obtain IAC-4-4 (6.56 g, yield 70%).

^{1 H-NMR: δ 5.93 (} d, 1H), 6.12 (t, 1H), 6.52 (m, 3H), 6.87 (m, 2H), 7.27 (m, 4H), 7.54 (d, 1H), 7.61 ( m, 2 H), 7.94 (m, 3 H)

<Step 3> Synthesis of IAC-4

Except that IAC-4-4 (8.07 g, 20.0 mmol) obtained in the above <Step 2> was used instead of IAC-1-4 used in <Step 5> of Preparation Example 1, 5 &gt; to obtain IAC-4 (4.68 g, yield 63%).

^{1 H-NMR: δ 5.93 (} d, 1H), 6.12 (t, 1H), 6.63 (m, 3H), 6.94 (m, 2H), 7.24 (m, 4H), 7.50 (t, 1H), 7.65 ( m, 2 H), 8.09 (d, 1 H), 10.34 (s, 1 H)

[Preparation Example 4] Synthesis of IAC-5 and IAC-6

<Step 1> Synthesis of IAC-5-1

Except that 1-bromo-4-iodobenzene (19.5 g, 69.0 mmol) was used in place of 1-bromo-2-iodobenzene used in <Step 1> of Preparation Example 1, The same procedure was followed to obtain IAC-5-1 (16.3 g, yield 74%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.48 (m, 3H), 7.63 (m, 3H), 7.99 (d, 1H), 8.31 (d, 1H)

<Step 2> Synthesis of IAC-5-2

Except that IAC-5-1 (8.07 g, 20.0 mmol) obtained in the above <Step 1> was used instead of IAC-1-1 used in <Step 2> of Preparation Example 1, 2 &gt;, IAC-5-2 (4.19 g, yield 74%) was obtained.

^{1 H-NMR: δ 5.92 (} d, 1H), 6.12 (t, 1H), 6.52 (d, 1H), 6.69 (s, 1H), 6.96 (d, 1H), 7.28 (m, 2H), 7.63 ( d, 1 H), 9.71 (s, 1 H)

<Step 3> Synthesis of IAC-5-3

Except that the IAC-5-2 (17.1 g, 60.0 mmol) obtained in the above Step 2 was used instead of the IAC-1-2 used in the <Step 3> of Preparation Example 1, 3 &gt;, IAC-5-3 (15.0 g, yield 79%) was obtained.

^{1 H-NMR: δ 5.93 (} d, 1H), 6.12 (t, 1H), 6.52 (d, 1H), 6.89 (s, 1H), 7.16 (d, 1H), 7.28 (d, 1H), 7.43 ( (d, IH), 7.63 (m, 2H), 8.01 (m, 3H), 9.74

<Step 4> Synthesis of IAC-5-4

Except that the IAC-5-3 (7.53 g, 23.0 mmol) obtained in the above Step 3 was used instead of the IAC-1-3 used in the <Step 4> of Preparation Example 1, 4 &gt; to obtain IAC-5-4 (6.45 g, yield 69%).

^{1 H-NMR: δ 5.92 (} d, 1H), 6.14 (t, 1H), 6.52 (d, 1H), 6.66 (m, 2H), 6.81 (m, 2H), 7.21 (m, 4H), 7.43 ( d, 1 H), 7.64 (m, 2 H), 8.02 (m, 3 H)

<Step 5> Synthesis of IAC-5 and IAC-6

Step 5 of Preparation Example 1 was repeated except that IAC-5-4 (8.07 g, 20.0 mmol) obtained in the above Step 4 was used instead of IAC-1-4 used in Step 5 of Preparation Example 1 (3.12 g, yield 42%) and IAC-6 (3.02 g, yield 39%) were obtained.

Of the ^{IAC-5 1 H-NMR:} δ 5.93 (d, 1H), 6.14 (t, 1H), 6.62 (m, 3H), 6.81 (t, 1H), 6.91 (d, 1H), 7.23 (m, 4H ), 7.48 (d, 1 H), 7.64 (m, 3H), 8.12 (d,

Of the ^{IAC-6 1 H-NMR:} δ 5.93 (d, 1H), 6.13 (t, 1H), 6.62 (m, 3H), 6.82 (t, 1H), 7.12 (s, 1H), 7.23 (m, 3H ), 7.62 (m, 4H), 8.12 (d, 1H), 10.43 (s,

[Synthesis Example 1] Synthesis of C-1

(3.71 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol) and Pd ₂ (dba) ₃ (T-Bu) ₃ P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to toluene (50 ml) and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, C-1 (5.07 g, yield 84%) was obtained by column chromatography.

MS [M + 1] &lt; ⁺ &gt; 603

[Synthesis Example 2] Synthesis of C-2

Except that 2-chloro-4,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, 1, the title compound C-2 (5.00 g, yield 83%) was obtained.

MS [M + 1] &lt; ⁺ &gt; 602

[Synthesis Example 3] Synthesis of C-3

Except that 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, 1, the title compound C-3 (4.94 g, yield 82%) was obtained.

MS [M + 1] &lt; ⁺ &gt; 602

[Synthesis Example 4] Synthesis of C-4

Except that 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 , The objective compound C-4 (4.88 g, yield 72%) was obtained by carrying out the same method as in Synthesis Example 1.

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 5] Synthesis of C-5

Except that 2- (4-chlorophenyl) -4,6-diphenylpyrimidine (3.43 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 , The objective Compound C-5 (5.09 g, yield 75%) was obtained by carrying out the same method as in Synthesis Example 1.

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 6] Synthesis of C-6

Except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00) was used in place of 2-chloro-4,6-diphenyl- mmol), the target compound C-6 (5.43 g, yield 80%) was obtained by carrying out the same processes as in Synthesis Example 1.

MS [M + 1] &lt; ⁺ &gt; 679

[Synthesis Example 7] Synthesis of C-7

(3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, The target compound C-7 (4.81 g, yield 71%) was obtained in the same manner as in Synthesis Example 1, except that 3-chlorophenyl) -4,6-diphenylpyrimidine (3.43 g, 10.00 mmol) was used.

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 8] Synthesis of C-8

(3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, The objective compound C-8 (4.68 g, yield 69%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-chlorophenyl) -2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) was used.

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 9] Synthesis of C-9

(3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 9- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole (3.76 g, 10.00 mmol) 4.27 g, yield 64%).

MS [M + 1] &lt; ⁺ &gt; 667

[Synthesis Example 10] Synthesis of C-10

(3-bromophenyl) triphenylene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine by using IAC-2 (3.71 g, 10.00 mmol) instead of IAC- (4.31 g, yield 64%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound (3.83 g, 10.00 mmol) was used.

MS [M + 1] &lt; ⁺ &gt; 674

[Synthesis Example 11] Synthesis of C-11

(3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and 3-bromo (4.43 g, yield 72%) was obtained in the same manner as in Synthesis Example 1, except that N, N-diphenylaniline (3.24 g, 10.00 mmol) was used.

MS [M + 1] &lt; ⁺ &gt; 615

[Synthesis Example 12] Synthesis of C-12

(3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, (4.60 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that 3-bromophenyl dibenzo [b, d] thiophene (3.39 g, 10.00 mmol) .

MS [M + 1] &lt; ⁺ &gt; 630

[Synthesis Example 13] Synthesis of C-13

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, IAC-2 (3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of IAC- The target compound C-13 (3.73 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that bromobiphenyl-3,5-dicarbonitrile (2.83 g, 10.00 mmol) was used.

MS [M + 1] &lt; ⁺ &gt; 574

[Synthesis Example 14] Synthesis of C-14

Except that the IAC-3 (3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used in place of the IAC-1 used in Synthesis Example 1, the target compound C-14 (4.94 g, , Yield: 82%).

MS [M + 1] &lt; ⁺ &gt; 603

[Synthesis Example 15] Synthesis of C-15

Except that the IAC-3 (3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used in place of the IAC-1 used in Synthesis Example 2, the target compound C-15 (4.33 g, , Yield: 72%).

MS [M + 1] &lt; ⁺ &gt; 602

[Synthesis Example 16] Synthesis of C-16

(4.29 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 3, except that IAC-3 (3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of IAC-1 used in Synthesis Example 3 , Yield: 71%).

MS [M + 1] &lt; ⁺ &gt; 602

[Synthesis Example 17] Synthesis of C-17

(5.22 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 4, except that IAC-3 (3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of IAC- , Yield: 77%).

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 18] Synthesis of C-18

(5.26 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 5, except that IAC-3 (3.71 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of IAC- , Yield: 78%).

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 19] Synthesis of C-19

(4.82 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of IAC-1 used in Synthesis Example 6, to thereby obtain the desired compound C-19 (4.82 g, , Yield: 71%).

MS [M + 1] &lt; ⁺ &gt; 679

[Synthesis Example 20] Synthesis of C-20

(5.56 g, 10.00 mmol) was obtained by carrying out the same procedure as in Synthesis Example 7, except that IAC-4 (3.71 g, 10.00 mmol) obtained in Preparation Example 3 was used instead of IAC-2 used in Synthesis Example 7 , Yield: 82%).

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 21] Synthesis of C-21

The procedure of Synthetic Example 8 was repeated, except that IAC-4 (3.71 g, 10.00 mmol) obtained in Preparation Example 3 was used instead of IAC-2 used in Synthetic Example 8 to obtain 5.66 g , Yield: 84%).

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 22] Synthesis of C-22

The same procedure as in Synthesis Example 9 was carried out, except that IAC-4 (3.71 g, 10.00 mmol) obtained in Preparation Example 3 was used in place of IAC-2 used in Synthesis Example 9 to obtain 5.60 g , Yield: 84%).

MS [M + 1] &lt; ⁺ &gt; 667

[Synthesis Example 23] Synthesis of C-23

The procedure of Synthesis Example 10 was repeated except that IAC-4 (3.71 g, 10.00 mmol) obtained in Preparation Example 3 was used instead of IAC-2 used in Synthesis Example 10 to obtain the desired compound C-23 (5.39 g, , Yield: 80%).

MS [M + 1] &lt; ⁺ &gt; 674

[Synthesis Example 24] Synthesis of C-24

The same procedure as in Synthesis Example 11 was carried out, except that IAC-4 (3.71 g, 10.00 mmol) obtained in Preparation Example 3 was used instead of IAC-2 used in Synthesis Example 11 to obtain the desired compound C-24 (5.10 g , Yield: 83%).

MS [M + 1] &lt; ⁺ &gt; 615

[Synthesis Example 25] Synthesis of C-25

(5.23 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 12, except that IAC-4 (3.71 g, 10.00 mmol) obtained in Preparation Example 3 was used instead of IAC- Yield: 83%).

MS [M + 1] &lt; ⁺ &gt; 630

[Synthesis Example 26] Synthesis of C-26

(5.10 g, 10.00 mmol) was obtained by following the same procedure as in Synthesis Example 13, except that IAC-4 (3.71 g, 10.00 mmol) obtained in Preparation Example 3 was used instead of IAC- Yield: 83%).

MS [M + 1] &lt; ⁺ &gt; 574

[Synthesis Example 27] Synthesis of C-27

(4.88 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of the IAC-1 used in Synthesis Example 1, to thereby obtain the desired compound C-27 (4.88 g, , Yield: 81%).

MS [M + 1] &lt; ⁺ &gt; 603

[Synthesis Example 28] Synthesis of C-28

(4.64 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 2, except that IAC-5 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of IAC-1 used in Synthesis Example 2, Yield: 77%).

MS [M + 1] &lt; ⁺ &gt; 602

[Synthesis Example 29] Synthesis of C-29

(4.29 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of the IAC-1 used in Synthesis Example 3, to thereby obtain the desired compound C-29 (4.29 g, , Yield: 71%).

MS [M + 1] &lt; ⁺ &gt; 602

[Synthesis Example 30] Synthesis of C-30

(5.22 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 4, except that IAC-5 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of IAC- , Yield: 77%).

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 31] Synthesis of C-31

The same procedure as in Synthesis Example 5 was carried out, except that the IAC-5 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of the IAC-1 used in Synthesis Example 5 to obtain the desired compound C-31 (5.70 g , Yield: 84%).

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 32] Synthesis of C-32

Except that the IAC-5 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of the IAC-1 used in Synthesis Example 6, the target compound C-32 (4.81 g, , Yield: 71%).

MS [M + 1] &lt; ⁺ &gt; 679

[Synthesis Example 33] Synthesis of C-33

(5.51 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 7, except that IAC-6 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of IAC-2 used in Synthesis Example 7 , Yield: 81%).

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 34] Synthesis of C-34

The procedure of Synthetic Example 8 was repeated, except that IAC-6 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of IAC-2 used in Synthetic Example 8 to obtain 5.97 g , Yield: 88%).

MS [M + 1] &lt; ⁺ &gt; 678

[Synthesis Example 35] Synthesis of C-35

The same procedure as in Synthesis Example 9 was carried out, except that IAC-6 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used in place of IAC-2 used in Synthesis Example 9 to obtain 5.40 g , Yield: 81%).

MS [M + 1] &lt; ⁺ &gt; 667

[Synthesis Example 36] Synthesis of C-36

The procedure of Synthetic Example 10 was repeated except that IAC-6 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of IAC-2 used in Synthesis Example 10 to obtain the desired compound C-36 (5.39 g, , Yield: 80%).

MS [M + 1] &lt; ⁺ &gt; 674

[Synthesis Example 37] Synthesis of C-37

(5.47 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 11, except that IAC-6 (3.71 g, 10.00 mmol) obtained in Preparation Example 6 was used instead of IAC- Yield: 89%).

MS [M + 1] &lt; ⁺ &gt; 615

[Synthesis Example 38] Synthesis of C-38

The same procedure as in Synthesis Example 12 was carried out, except that IAC-6 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of IAC-1 used in Synthesis Example 12 to obtain 5.23 g , Yield: 83%).

MS [M + 1] &lt; ⁺ &gt; 630

[Synthesis Example 39] Synthesis of C-39

(4.13 g, 10.00 mmol) was obtained in the same manner as in Synthesis Example 13, except that IAC-6 (3.71 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of IAC-2 used in Synthesis Example 13 , Yield: 72%).

MS [M + 1] &lt; ⁺ &gt; 574

[Example 1] Production of green organic EL device

Compound C-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was fabricated according to the following procedure.

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

(60 nm) / TCTA (80 nm) / C-1 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF 1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

[Example 2] - [Example 39] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that the compound described in Table 1 was used instead of the compound C-1 used as the host material in Example 1.

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used in place of the compound C-1 used as a light emitting host material in the light emitting layer formation in Example 1. The structure of CBP used here is as described in Example 1. [

[Evaluation example]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the green organic EL devices manufactured in Examples 1 to 39 and Comparative Example 1, and the results are shown in Table 1 below .

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 C-1 6.74 517 41.4 Example 2 C-2 6.69 518 40.9 Example 3 C-3 6.61 517 40.1 Example 4 C-4 6.79 516 40.3 Example 5 C-5 6.72 518 39.8 Example 6 C-6 6.71 518 39.5 Example 7 C-7 6.80 517 40.9 Example 8 C-8 6.71 518 40.1 Example 9 C-9 6.70 517 39.3 Example 10 C-10 6.79 517 40.3 Example 11 C-11 6.75 518 40.6 Example 12 C-12 6.90 518 40.7 Example 13 C-13 6.69 516 39.1 Example 14 C-14 6.86 518 39.5 Example 15 C-15 6.88 517 39.3 Example 16 C-16 6.74 518 40.5 Example 17 C-17 6.74 518 39.3 Example 18 C-18 6.70 517 39.3 Example 19 C-19 6.61 516 39.1 Example 20 C-20 6.79 518 40.3 Example 21 C-21 6.75 517 40.2 Example 22 C-22 6.74 517 41.2 Example 23 C-23 6.75 518 39.1 Example 24 C-24 6.79 517 39.3 Example 25 C-25 6.75 518 39.3 Example 26 C-26 6.78 517 39.5 Example 27 C-27 6.78 518 39.6 Example 28 C-28 6.79 516 40.7 Example 29 C-29 6.79 517 39.8 Example 30 C-30 6.80 516 40.0 Example 31 C-31 6.80 516 40.1 Example 32 C-32 6.81 517 40.2 Example 33 C-33 6.81 516 40.3 Example 34 C-34 6.82 517 39.6 Example 35 C-35 6.82 518 40.6 Example 36 C-36 6.69 515 40.2 Example 37 C-37 6.83 515 39.6 Example 38 C-38 6.84 518 40.9 Example 39 C-39 6.61 517 40.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL devices of Examples 1 to 39, in which the compounds (C-1 to C-39) according to the present invention were used as the host of the light emitting layer, The organic EL device of the present invention exhibits better efficiency and better driving voltage than the green organic EL device of the related art.

Claims (11)

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

In Formula 1,
X ₁ and X ₂ are the same as or different from each other, and each independently C (R ₈ ) or N, where R ₈ is plural, they are the same or different from each other;
One of R ₁ to R ₈ is bonded to an adjacent group to form a condensed ring represented by the following formula (2);
(2)

In the formula (2), the dotted line represents a moiety which is condensed with the formula (1)
Y ₁ and Y ₂ are the same or different, each independently represent _{N (Ar 1), O,} S, C (Ar 2) (Ar 3) and Si (Ar ₄₎ is selected from the group consisting of (Ar ₅₎ , Provided that at least one of Y ₁ and Y ₂ is N (Ar ₁ ), provided that when Ar ₁ is plural, they are the same as or different from each other;
Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, A heterocyclic alkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group , is selected from the aryl phosphine oxide group, and the group consisting of a C ₆ ~ C ₄₀ aryl silyl group of C ₆ ~ C _40,
R ₁ to not form a condensed ring of the general formula 2 R ₈ and R ₉ to R ₁₂ is the same as a nitro group, or different and each independently represent hydrogen, deuterium (D), a halogen, cyano group, C ₁ ~ C with each other _A C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group , A heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of the An arylamine group, or may be bonded to an adjacent group to form a condensed ring,
The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the aryl group of the R ₁ to R ₁₂ and Ar ₁ to Ar ₅ The silyl group, the alkyl boron group, the aryl boron group, the aryl phosphine group, the aryl phosphine oxide group and the arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ or aryl amines It may be substituted, and, just when the plurality of substituents, they may be the same or different from each other. The method according to claim 1,
Wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (3) to (8):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above Formulas 3 to 8,
X ₁ , X ₂ , Y ₁ , Y _2, and R ₁ to R ₁₂ are as defined in claim 1, respectively. The method according to claim 1,
Y ₁ and Y ₂ are both N (Ar ₁ )
A plurality of Ar &lt; _{1 &gt;} may be the same or different from each other,
Wherein Ar &_lt; 1 _&gt; is as defined in claim 1. The method according to claim 1,
X ₁ and X ₂ are both C (R ₈ )
A plurality of R &lt; ₈ &gt; may be the same or different from each other,
And R &lt; ₈ &gt; are as defined in claim 1. The method according to claim 1,
Ar ₁ to Ar ₅ are the same or different, and each independently C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₆ ~ arylamine group of C ₄₀ and C ₆ ~ C ₄₀ &Lt; / RTI &gt;&lt; RTI ID = 0.0 &gt;
The aryl group, heteroaryl group, arylamine group and arylsilyl group of Ar ₁ to Ar ₅ are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkoxy group, group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ alkyloxy A C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting of an aryl amine of the C ₆₀ or may be unsubstituted, Provided that when the substituents are plural, they may be the same or different from each other. The method according to claim 1,
R ₁ to R ₈ and R ₉ to R ₁₂ in which the condensed ring of Formula 2 is not mutually the same or different are each independently selected from the group consisting of hydrogen, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₆ to C ₆₀ aryl group, an aryl nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60,
In this case, the R ₁ to R ₈ and R ₉ to R alkyl group of _12, an aryl group, a heteroaryl group and the arylamine group are each independently C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ alkynyl group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group of ₆₀ arylboronic, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one substituent at least one selected from the group consisting of an aryl amine of the C ₆₀ unsubstituted in , Provided that when the substituent is plural, they may be the same or different from each other. The method according to claim 1,
At least one of R ₁ to R ₈ and R ₉ to R ₁₂ in which Ar ₁ and the condensed ring of formula (2) are not formed is a substituent represented by the following formula (9), and the remainder is as defined in claim 1 compound:
[Chemical Formula 9]

In the above formula (9)
L is a single bond or is selected from the group consisting of C ₆ to C ₄₀ arylene groups and heteroarylene groups having 5 to 40 nuclear atoms;
Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₁₃ ), provided that at least one of Z ₁ to Z ₅ is N, and when R ₁₃ is plural, Different;
R ₁₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl group, and a phosphine oxide selected from the group consisting of C ₆ ~ C ₆₀ aryl group of an amine or of, or coupled to adjacent groups may form a condensed ring;
At this time, the arylene group and heteroaryl group, and the alkyl group of said R _13, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group in the L, alkylsilyl group , An arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkenyl group, C ₆ -C ₆₀ alkyloxy, C ₆ -C ₆₀ aryloxy, C ₃ -C ₄₀ alkylsilyl, C ₆ -C ₆₀ arylsilyl, C ₁ -C ₄₀ alkylboron, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted 1 or more selected from the group consisting of an aryl amine of the C ₆₀ of the When substituted or may be unsubstituted, but a plurality of the said substituent, they may be the same or different from each other. The method according to claim 1,
At least one of R ₁ to R ₈ and R ₉ to R ₁₂ in which Ar ₁ and the condensed ring of Formula 2 are not formed is selected from the group consisting of substituents represented by the following formulas A-1 to A-15, A compound as defined in claim 1:

In the above formulas A-1 to A-15,
L is a single bond or is selected from the group consisting of C ₆ to C ₄₀ arylene groups and heteroarylene groups having 5 to 40 nuclear atoms;
When there are plural R &lt; _{13 &} gt ;, they are the same or different from each other,
R ₁₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl group, and a phosphine oxide selected from the group consisting of C ₆ ~ C ₆₀ aryl group of an amine or of, or coupled to adjacent groups may form a condensed ring;
n is an integer of 0 to 4, and when n is an integer of 1 to 4, R ₂₁ is a group selected from the group consisting of deuterium (D), a halogen, a cyano group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, _A substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine of the ring oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl groups, or they may be bonded to adjacent groups to form a condensed ring;
In this case, the alkyl group of the L-arylene group, and a heteroaryl group, R ₁₃ a, 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 group, an aryl silyl groups, alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, an alkyl group of R _21, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkyl A silyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ Al Boron group, one member selected from the group consisting of C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ with an aryl amine of the C ₆₀ of the And the substituents may be the same or different from each other when the substituent is plural. 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 8. 10. The method of claim 9,
Wherein at least one organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, and a light emitting layer. 10. The method of claim 9,
The organic compound layer containing the compound is a light emitting layer,
In the light emitting layer, the compound is a phosphorescent host.