KR20150011422A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound represented by chemical formula 1, and to an organic electroluminescent device comprising the same. According to the present invention, the compound is used in an organic matter layer, desirably a light emitting layer, thereby improving light emitting efficiency, driving voltage, and life of the organic electroluminescent device.

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 and holes are injected into the organic layer, respectively. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. A material used as an organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

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

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. The development of phosphorescent materials can theoretically improve luminescent efficiency up to four times that of fluorescent materials, so attention has focused on phosphorescent dopant materials as well as phosphorescent host materials.

Up to now, hole injection materials, hole transport materials. NPB, BCP, and Alq ₃ are known as hole blocking materials and electron transporting materials, and an anthracene derivative is known as a fluorescent dopant / host material among luminescent materials. In addition, and a phosphorescent dopant material, which has an advantage in improving the efficiency aspect of the luminescent material is a metal complex compound containing Ir such as _{Firpic, Ir (ppy) 3,} (acac) Ir (btp) 2 is known, as a phosphorescent host material Is known as CBP.

However, conventional luminescent materials are good in terms of luminescence characteristics, but have poor thermal stability due to low glass transition temperature, and thus are not satisfactory in terms of lifetime of an organic electroluminescent device. Therefore, development of a luminescent material having excellent performance is required.

Japanese Patent Application Laid-Open No. 2001-160489

It is an object of the present invention to provide a novel organic compound having a light emitting ability, a hole transporting ability and a hole injecting ability.

In addition, the present invention relates to a novel organic An organic electroluminescent device including a compound having a low driving voltage, a high luminous efficiency and an improved lifetime.

In order to accomplish the above object, the present invention provides a compound represented by the following general formula (1).

[Chemical Formula 1]

Wherein one of R ₁ and R ₂ , R ₂ and R ₃ , or one of R ₃ and R ₄ forms a condensed ring represented by the following formula (2), R ₁ to R ₅ each independently represent hydrogen, deuterium , A halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl 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, of to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ of the aryloxy group, C-alkyl silyl group of _{3 ~ C 40, C 6 ~} C 60 aryl silyl group, C ₂ ~ 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 >

(2)

R ₆ to R ₉ are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl 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, a C ₆ to C ₆₀ arylsilyl group, a C ₂ 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 group, and a C ₆ ~ C ₆₀ aryl group of an amine selected from the group consisting of and, wherein, R ₆ to R ₉ At least one of them is represented by the following formula (3)

(3)

Wherein L ₁ represents a single bond or an arylene group having ₆ to ₆₀ carbon atoms or a heteroarylene group having 5 to 60 nuclear atoms and X ₁ Is selected from the group consisting of O, S, Se and NAr ₃ , and Y ₁ And Y ₂ are each independently N or CR ₁₀ and R ₁₀ and R ₂₁ to R ₂₄ each independently represent hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ a cycloalkyl group, a nuclear atoms, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heteroaryl of nuclear atoms of 5 to 60 aryl group, an alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₂ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ An arylphosphine group of C ₆ to C ₆₀ , an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ , or may be bonded to adjacent groups to form a condensed ring,

Ar ₁ to Ar ₃ are each independently a C ₆ to C ₁₈ aryl group or a heteroaryl group having 5 to 18 nuclear atoms,

The arylene group and the heteroarylene group of L < ₁ > and the Ar < _{1 >} To Ar _3, R ₁ to R ₁₀ and R ₂₁ to alkyl groups of R _24, 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 A halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, a number of 3 nucleus atoms, an aryl group, an aryloxy group, an aryloxy group and an arylamine group, 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 ₁ to C ₆₀ heteroaryl group, C ₄₀ alkylsilyl group, a group C ₆ ~ C ₆₀ aryl silyl, C ₂ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of. When the substituent is substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.

Also, the present invention is 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 is a compound represented by the above- And an organic electroluminescent device.

One or more organic layers including the compound represented by Formula 1 may be selected from the group consisting of a hole transporting layer, a hole injecting layer, and a light emitting layer, and preferably a hole transporting layer and / or a light emitting layer, and more preferably a light emitting layer.

The compound represented by Formula 1 may be a phosphorescent host material in the light emitting layer.

The term "alkyl" used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

"Alkenyl" used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, and the like.

"Alkynyl" used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Non-limiting examples thereof include ethynyl, 2-propynyl, and the like.

The term "cycloalkyl" used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

'Heterocycloalkyl' used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 atoms and includes at least one carbon in the ring, One to three carbons are replaced by a heteroatom such as N, O or S; Non-limiting examples thereof include morpholine, piperazine, and the like.

"Aryl" used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. At this time, the two or more rings may be attached to each other in a simple attached or condensed form. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.

The "heteroaryl" used in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, To three carbons are substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). At this time, the heteroaryl may be attached in a form in which two or more rings are attached or condensed to each other, and may further include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.

The term "alkyloxy" used in the present invention means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms and may have a linear, branched or cyclic structure . Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

As used herein, 'aryloxy' means a monovalent functional group represented by R'O- and R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.

As used herein, 'alkylsilyl' means silyl substituted with alkyl having 1 to 40 carbon atoms, 'arylsilyl' means silyl substituted with aryl having 6 to 60 carbon atoms, arylamine has 6 to 60 carbon atoms ≪ / RTI > aryl substituted by aryl of the formula

As used herein, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

Since the compound according to the present invention is excellent in heat resistance, hole injecting ability, hole transporting ability, and light emitting ability, it can be used as an organic material layer of an organic electroluminescent device, preferably as a hole injecting layer material, a hole transporting layer material, .

In addition, the organic electroluminescent device including the compound according to the present invention in the hole injection layer, the hole transporting layer, and / or the light emitting layer can greatly improve aspects of light emitting performance, driving voltage, lifetime, efficiency, Panel or the like.

Hereinafter, the present invention will be described.

1. New compound

The novel organic compound according to the present invention is characterized in that an indole-based moiety is bonded to an end of a pyrazolabazole-based moiety in which an indazole-based moiety and an indole-based moiety are condensed. ) And a pyrazolabazazole-based moiety in which an indole-based moiety is condensed are directly bonded to each other or bonded to each other by a linking group (e.g., an arylene group or the like) to form a basic skeleton, Is a structure having various substituents bonded thereto, and is characterized by being represented by the above formula (1).

The compound represented by Chemical Formula 1 has a higher molecular weight than that of a material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')) applied to an organic electroluminescent device and has a high glass transition temperature, great.

On the other hand, the host material contained in the phosphorescent light emitting layer among the organic material layers included in the organic electroluminescent device must have a higher triplet energy gap than the dopant material. That is, in order to effectively provide phosphorescence from the dopant material, the lowest excitation state of the host material must be higher than the lowest emission state of the dopant material. The energy level of the compound represented by Formula 1 can be effectively controlled by introducing various substituents into the condensed pyrazolabazazole-based moiety having a broad singlet energy level and a high triplet energy level. The compound represented by the above formula (1) is also effective for inhibiting crystallization of the organic material layer.

In addition, the compound represented by Formula 1 has a structure in which an electron-withdrawing group (EWG) having a high electron absorbing property is bonded, so that the bonding force between holes and electrons can be enhanced because the whole molecule has bipolar characteristics.

As described above, the compound represented by Formula 1 can improve phosphorescence characteristics of the organic electroluminescent device, improve hole injection / transport ability, luminous efficiency, driving voltage, lifetime characteristics, etc., The electron transporting ability and the like can be improved. Accordingly, the compound represented by Formula 1 according to the present invention may be used as an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), a hole transporting layer material, Can be used.

The compound represented by the formula (1) of the present invention is preferably selected from the group consisting of compounds represented by the following formulas (1a) to (1f).

[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

≪ RTI ID = 0.0 &

[Formula 1e]

(1f)

In formulas (1a) to (1f), Ar ₁ , Ar ₂ and R ₁ To R < ₉ > are the same as defined in the above formula (1). Wherein at least one of R ₆ to R ₉ is selected from the above-mentioned formula (3), among which R ₈ is preferably represented by the formula (3).

On the other hand, in the general formula (3), L ₁ is R ₂₁ It is connected to R ₂₃ to R ₂₃ of the preferred. The formula (3) is preferably selected from the group consisting of the structures represented by the following formulas (3a) to (3h).

[Chemical Formula 3]

(3b)

[Chemical Formula 3c]

(3d)

[Formula 3e]

(3f)

[Formula 3g]

[Chemical Formula 3h]

In the above formulas (3a) to (3h), X ₁ , Y ₁ , Y ₂ and R ₂₁ To R < ₂₄ > are the same as defined in the above formula (3). At this time, X ₁ is preferably NAr _3, and X ₂ is chosen from O, S, Se and NAr _4, among them preferably a NAr _4.

In addition, Y ₃ And Y ₄ is the each independently N or CR _12, wherein, Y ₃ And Y < ₄ > If CR _12, a plurality of CR ₁₂ may be the same or different from each other.

Wherein R ₁₂ and R ₂₅ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ a C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₁ ~ C ₄₀ alkyl silyl group, a alkyl boronic of _{C 1 ~ C 40, C 6} ~ C group ₄₀ arylboronic of, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or the adjacent groups bonded to the condensed ring of Can be formed.

Ar ₄ is a C ₆ to C ₁₈ aryl group or a heteroaryl group having 5 to 18 nuclear atoms, and m is an integer of 0 to 4.

On the other hand, the Ar ₄ of the aryl group, a heteroaryl group, the R ₁₂ and the alkyl group of R _25, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic The arylphosphine oxide group and the arylsilyl group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms A cycloalkyl group, 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 ₁ to C ₄₀ alkyl A silyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₂ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ aryl A phosphine oxide group and an arylamine group having ₆ to ₆₀ carbon atoms. Specifically, it is preferably substituted with at least one member selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group and heteroaryl group having 5 to 60 nuclear atoms. When the substituent is substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.

In the general formulas (1), (2) and (3), Ar ₁ to Ar ₃ are each independently a C ₆ to C ₁₈ aryl group or a heteroaryl group having 5 to 18 nucleus atoms, wherein at least one of desirable.

[Chemical Formula 4]

In the above formula (4), and * means a part joined to the formula 1, 2 and 3, L ₂ Or a heteroarylene group having 5 to 18 nucleus atoms, Z ₁ to Z ₅ are each independently N or CR ₁₁ , and at least _{one of} Z ₁ to Z ₅ is a single bond or a C ₆ to C ₁₈ arylene group or a heteroarylene group having 5 to 18 nuclear atoms, One is N and R ₁₁ is hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₆ to C ₄₀ aryl, C ₃ to C ₄₀ cycloalkyl, A heterocycloalkyl group, Nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl Group, or may be bonded to an adjacent group to form a condensed ring,

Alkyl groups of the L ₂ of the aryl group, a heteroaryl group, the R _11, an aryl group, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boronic group , Arylboron group, arylsilyl group, arylphosphine group and arylphosphine oxide group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, 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 ₁ to C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of. At this time, when there are a plurality of substituents, they may be the same or different.

It is more preferable that the formula (4) is selected from the group consisting of the structures represented by the following A-1 to A-15.

In the above A-1 to A-15,

L ₂ and R ₁₁ are the same as defined in the above formula (4), a plurality of R _{11 s} are the same as or different from each other,

R ₂₆ is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group C C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C _An arylphosphine group having ₆ to ₄₀ carbon atoms, an arylphosphine oxide group having ₆ to ₄₀ carbon atoms, and an arylsilyl group having ₆ to ₄₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring,

n is an integer of 0 to 4;

Where the alkyl group of said R _26, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl Each of which is independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine which may be substituted with oxide groups and one or more substituents selected from the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl. When the substituent is substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.

Among the Ar ₁ to Ar ₃ , the C ₆ to C ₁₈ aryl group or the heteroaryl group having 5 to 18 nucleus atoms, which is not represented by the general formula (4), among them, a phenyl group, an acridine group, , And 5-triazine group.

In the above formulas (3) and (4), L ₁ And L ₂ are each independently a single bond or a phenylene group or a biphenylene group.

The compound represented by the formula (1) of the present invention can be specifically represented by the following compounds (C1 to C60), but is not limited thereto.

2. Organic Field  Light emitting element

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

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compound represented by the formula (1) may be used singly or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. In this case, the organic compound layer containing the compound represented by Formula 1 is preferably a light emitting layer.

The light emitting layer of the organic electroluminescent device according to the present invention may include a host material, and may include a compound represented by the above formula (1) as a host material. When the compound represented by Formula 1 is incorporated as a light emitting layer material of an organic electroluminescent device, preferably a green phosphorescent host, the bonding strength between holes and electrons in the light emitting layer is increased. Therefore, the efficiency of the organic electroluminescent device ), Lifetime, luminance, driving voltage and the like can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. At this time, at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Chemical Formula 1, and preferably the light emitting layer may include the compound represented by Chemical Formula 1 have. At this time, the compound of the present invention can be used as a phosphorescent host material of the light emitting layer. On the other hand, an electron injection layer may be further stacked on the electron transporting layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which not only an anode, one or more organic compound layers and a cathode are sequentially laminated but also an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic compound layer.

The organic electroluminescent device of the present invention may be manufactured by using materials and methods known in the art, except that at least one or more of the organic material layers (for example, the light emitting layer) An organic layer and an electrode.

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

The substrate may be a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or a sheet, but is not limited thereto.

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 or polyaniline; And 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; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[ Preparation Example  One] IC Synthesis of -1

≪ Step 1 > 5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1H- indazole  synthesis

(25.22 g, 0.128 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3 , 2-dioxaborolane) (48.58 g , 0.191 mol), Pd (dppf) Cl 2 (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and a mixture of 1,4-dioxane (500 ml) and 130? Lt; / RTI > for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 5- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -1H-indazole (22.49 g, yield 72%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.60 (d, 1H), 8.15 (m, 2H), 8.34 (d, 1H), 12.34 (s, 1H)

≪ Step 2 > 5- (5- chloro -2- nitrophenyl ) -1H- indazole Synthesis of

4-chloro-2-iodo-1-nitrobenzene (21.37 g, 75.41 mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -1H-indazole ( 22.09 g, 90.49 mmol), NaOH (9.05 g, 226.24 mmol) and _{THF / H 2 O (400 ml} / 200 ml) , and then, Pd (PPh ₃ eseo 40? mix) ₄ (4.36 g, 5 mol%) was added thereto, and the mixture was stirred at 80? 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. 5-chloro-2-nitrophenyl) -1H-indazole (15.60 g, yield: 63%) was obtained by removing the solvent from the obtained organic layer and then purifying by column chromatography (Hexane: EA = 3: 1 (v / v) ≪ / RTI >

¹ H-NMR:? 7.63 (d, IH), 7.71 (d, IH), 8.07 (s, IH), 8.20 (s, IH), 8.26 (m, 2H), 8.38 s, 1 H)

≪ Step 3 > 5- (5- chloro -2- nitrophenyl )-One- phenyl -1H- indazole Synthesis of

(12.63 g, 46.17 mmol), iodobenzene (14.13 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol) obtained in the above Step 2 ), K ₂ CO ₃ (6.38 g, 46.17 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° 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 . After removing the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to give 5- (5-chloro-2-nitrophenyl) 11.46 g, yield 71%).

^{1 H-NMR: δ 7.45 (} m, 1H), 7.63 (m, 6H), 8.07 (s, 1H), 8.26 (m, 2H), 8.38 (m, 2H)

<Step 4> 7- chloro -3- phenyl -3,10- dihydropyrazolo Synthesis of [4,3-a] carbazole

Phenyl-1H-indazole (5.56 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) and 1,2- dichlorobenzene (50 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 obtained organic layer with MgSO ₄ and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 7-chloro-3-phenyl-3,10- dihydropyrazolo [ a] carbazole (2.68 g, yield 53%).

^{1 H-NMR: δ 7.09 (} d, 1H), 7.42 (m, 2H), 7.59 (m, 6H), 8.35 (m, 2H), 10.05 (s, 1H)

<Step 5> IC Synthesis of -1

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (2.59 g, 7.03 mmol) was reacted with 9-phenyl-3- 7-chloro-3-phenyl- 3,10-dihydropyrazolo [4,3-a] carbazole (2.68 g, 8.43 mmol), NaOH (0.84 g, 21.08 mmol) and _{THF / H 2 O (40 ml} / 20 ml obtained ), And Pd (PPh ₃ ) ₄ (0.48 g, 5 mol%) was added thereto at 40 ° _C and stirred at 80 ° _C 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. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain IC-1 (1.77 g, yield 66%).

¹ H-NMR:? 7.50 (m, 17H), 7.88 (m, 3H), 8.34

[ Preparation Example  2] IC Synthesis of -2

Phenyl-2-yl) -9H-carbazole instead of the 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Step 4 of Preparation Example 1 was repeated except for using 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (2.59 g, 7.03 mmol) Gt; IC-2 < / RTI > was obtained.

¹ H-NMR:? 7.44 (m, 15H), 7.80 (m, 4H), 8.18 (d,

[ Preparation Example  3] IC Synthesis of -3

Phenyl-5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole used in Step 4 of Preparation Example 1 was used instead of 9- Step 4 of Preparation Example 1 was repeated except for using 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (2.25 g, 7.03 mmol) Gt; IC-3 < / RTI > was obtained.

¹ H-NMR:? 7.42 (m, 3H), 7.61 (m, IH), 7.78 (s, IH), 7.87 s, 1 H)

[ Preparation Example  4] IC Synthesis of -4

<Step 1> 7- chloro -3,10- 피덴 -3,10- dihydropyrazolo Synthesis of [4,3-a] carbazole

Chloro-3-phenyl-3,10-diol obtained in Step 4 of Preparation Example 1 was used instead of 5- (5-chloro-2-nitrophenyl) The procedure of Step 3 of Preparation Example 1 was repeated except that dihydropyrazolo [4,3-a] carbazole (14.67 g, 46.17 mmol) was used to prepare 7-chloro-3,10-diphenyl- 10-dihydropyrazolo [4,3-a] carbazole (14.72 g, yield 81%).

^{1 H-NMR: δ 7.09 (} d, 1H), 7.52 (m, 11H), 7.87 (d, 1H), 8.05 (s, 1H), 8.33 (m, 2H)

&Lt; Step 2 > 3,10- 피덴 -7- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -3,10-dihydropyrazolo [4,3-a] carbazole

3 -10-diphenyl-3,10-dihydropyrazolo [4,3-a] carbazole (prepared in Step 1 above) instead of 5-bromo-1H-indazole used in Step 1 of Preparation Example 1 14.72 g, 37.39 mmol) was used in the same manner as in <Step 1> of Preparation Example 1, except that 3,10-diphenyl-7- (4,4,5,5-tetramethyl-1,3 , 2-dioxaborolan-2-yl) -3,10-dihydropyrazolo [4,3-a] carbazole (12.34 g, yield 68%).

^{1 H-NMR: δ 1.23 (} s, 12H), 7.50 (m, 12H), 7.96 (m, 2H), 8.34 (m, 2H)

<Step 3> IC Synthesis of -4

3-bromo-9H-carbazole (5.21 g, 21.19 mmol) was used instead of 4-chloro-2-iodo-1-nitrobenzene used in Step 2 of Preparation Example 1, Diphenyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole in place of 5-tetramethyl-1,3,2-dioxaborolan- IC-4 was obtained by carrying out the same procedure as <Step 2> of Preparation Example 1, except that 1-yl-3,10-dihydropyrazolo [4,3-a] carbazole (12.34 g, 25.43 mmol) .

^{1 H-NMR: δ 7.29 (} t, 1H), 7.58 (m, 14H), 7.77 (s, 2H), 7.87 (d, 1H), 8.00 (d, 1H), 8.14 (m, 2H), 8.34 ( m, 2 H), 10.24 (s, 1 H)

[ Preparation Example  5] IC Synthesis of -5

Except that 5-bromo-1H-indazole (4.17 g, 21.19 mmol) was used instead of 3-bromo-9H-carbazole used in <Step 3> of Preparation Example 4, The same procedure was followed to obtain IC-5.

^{1 H NMR: δ 7.58 (m} , 12H), 7.77 (s, 1H), 7.99 (d, 1H), 8.07 (s, 1H), 8.19 (m, 2H), 8.35 (m, 3H), 12.39 (s , 1H)

[ Preparation Example  6] IC Synthesis of -6

7-chloro-3-phenyl-3,10-dihydropyrazolo [4,3-a] carbazole (6.73 g, 21.19 mmol) was used instead of 3-bromo-9H-carbazole used in Step 3 of Preparation Example 4 , IC-6 was obtained by carrying out the same procedure as < Step 3 > of Preparation Example 4.

^{1 H NMR: δ 7.57 (m} , 18H), 7.76 (s, 2H), 7.88 (d, 1H), 8.02 (d, 1H), 8.18 (d, 1H), 8.36 (m, 4H), 10.21 (s , 1H)

[ Preparation Example  7] IC Synthesis of -7

<Step 1> 5- (4- chloro -2- nitrophenyl ) -1H- indazole  synthesis

Except that 4-chloro-1-iodo-2-nitrobenzene (21.37 g, 75.41 mmol) was used instead of 4-chloro-2-iodo-1-nitrobenzene used in Step 2 of Preparation Example 1 (4-chloro-2-nitrophenyl) -1H-indazole (14.61 g, yield 59%) was obtained in the same manner as in <Step 2> of Example 1.

¹ H-NMR: 8 7.63 (d, 1 H), 7.99 (m, 3 H), 8.18

<Step 2> Synthesis of 5- (4- chloro -2- nitrophenyl )-One- phenyl -1H- indazole  synthesis

5- (4-chloro-2-nitrophenyl) -1H-indazole (12.63 g, 46.17 mmol) was used in place of 5- (5-chloro-2- nitrophenyl) (4-chloro-2-nitrophenyl) -1-phenyl-1H-indazole (11.78 g, yield 73%) was obtained by following the procedure of <Step 3> of Preparation Example 1 .

¹ H-NMR: 8 7.45 (m, 1 H), 7.60 (m, 5 H), 7.97

<Step 3> 8- chloro -3- phenyl -3,10- dihydropyrazolo Synthesis of [4,3-a] carbazole

(4-chloro-2-nitrophenyl) -1-phenyl-1H-indazole was used instead of 5- (5-chloro-2-nitrophenyl) 3-phenyl-3,10-dihydropyrazolo [4,3-a] carbazole (5.56 g, 15.91 mmol) was used in the same manner as Step 4 of Preparation Example 1, (2.68 g, yield 53%).

¹ H-NMR:? 7.01 (d, 1 H), 7.42 (m, 3H), 7.60 (m, 4H), 8.06 (d,

<Step 4> IC - 7's  synthesis

3-phenyl-3,10-dihydropyrazolo [4,3-b] pyridine instead of the 7-chloro-3-phenyl-3,10-dihydropyrazolo [4,3- -a] carbazole (2.68 g, 8.43 mmol) was used in place of acetic anhydride. IC-7 was obtained in the same manner as in <Step 5> of Preparation Example 1.

¹ H-NMR:? 7.50 (m, 15H), 7.89 (m, 4H), 8.18 (d,

[ Synthetic example  1] Synthesis of C-1

(6.97 g, 13.29 mmol), bromobenzene (4.17 g, 26.57 mmol), Cu powder (0.17 g, 2.66 mmol) and K ₂ CO ₃ (3.66 g, 26.57 mmol) obtained in Preparation Example 1, Na ₂ SO ₄ (3.78 g, 26.57 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C for 12 hours.

After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound C-1 (5.27 g, yield 66%).

GC-Mass (theory: 600.71 g / mol, measurement: 600 g / mol)

[ Synthetic example  2] Synthesis of C-2

The same procedure as in Synthesis Example 1 was repeated, except that 2- (4-bromophenyl) triphenylene (10.18 g, 26.57 mmol) was used instead of bromobenzene used in Synthesis Example 1 to obtain C-2 (7.80 g, Yield: 71%).

GC-Mass (theory: 826.98 g / mol, measurement: 826 g / mol)

[ Synthetic example  3] Synthesis of C-3

The procedure of Synthesis Example 1 was repeated except that 4- (3-bromophenyl) dibenzo [b, d] thiophene (9.01 g, 26.57 mmol) was used instead of bromobenzene used in Synthesis Example 1, -3 (7.80 g, yield 75%).

GC-Mass (theory: 782.95 g / mol, measured: 782 g / mol)

[ Synthetic example  4] Synthesis of C-4

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (9.74 g, 26.57 mmol) was used instead of bromobenzene used in Synthesis Example 1 To obtain the target compound C-4 (7.04 g, yield 62%).

GC-Mass (calculated: 854.99 g / mol, measured: 854 g / mol)

[ Synthetic example  5] Synthesis of C-5

The procedure of Synthesis Example 1 was repeated except that 2-bromo-4,6-diphenyl-1,3,5-triazine (8.29 g, 26.57 mmol) was used instead of bromobenzene used in Synthesis Example 1, Compound C-5 (5.72 g, yield 57%) was obtained.

GC-Mass (calculated: 755.87 g / mol, measured: 755 g / mol)

[ Synthetic example  6] Synthesis of C-6

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (10.31 g, 26.57 mmol) was used instead of bromobenzene used in Synthesis Example 1, To obtain the objective compound C-6 (8.84 g, yield 80%).

GC-Mass (calculated: 831.96 g / mol, measured: 831 g / mol)

[ Synthetic example  7] Synthesis of C-7

Except that IC-2 (6.97 g, 13.29 mmol) obtained in Preparation Example 2 was used instead of IC-1 used in Synthesis Example 1 and 2-bromo-4-phenylquinazoline (7.58 g, 26.57 mmol) was used in place of bromobenzene , The target compound C-7 (7.94 g, yield 82%) was obtained in the same manner as in Synthesis Example 1.

GC-Mass (calculated: 728.84 g / mol, measured: 728 g / mol)

[ Synthetic example  8] Synthesis of C-8

(4'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (prepared in Synthesis Example 7) instead of 2-bromo- 12.34 g, 26.57 mmol), the target compound C-8 (8.45 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 7.

GC-Mass (theory: 908.06 g / mol, measurement: 908 g / mol)

[ Synthetic example  9] Synthesis of C-9

4-bromo-N, N-diphenylaniline (8.61 g, 26.57 mmol) was used instead of bromobenzene using IC-3 (6.32 g, 13.29 mmol) synthesized in Preparation Example 3 instead of IC- (5.25 g, yield 55%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that

GC-Mass (calculated: 718.85 g / mol, measured: 718 g / mol)

[ Synthetic example  10] Synthesis of C-10

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (8.42 g, 26.57 mmol) was used in place of 4-bromo-N, N-diphenylaniline used in Synthesis Example 9 , And the procedure of Synthetic Example 9 was repeated to obtain the compound C-10 (8.64 g, yield 86%).

GC-Mass (calculated: 755.87 g / mol, measured: 755 g / mol)

[ Synthetic example  11] Synthesis of C-11

IC-4 (6.97 g, 13.29 mmol) obtained in Preparation Example 4 was used in place of IC-1 used in Synthesis Example 1 and 1-bromo-3,5-diphenylbenzene (8.22 g, 26.57 mmol) was used instead of bromobenzene , The target compound C-11 (7.80 g, yield 78%) was obtained by carrying out the same procedure as in Synthesis Example 1.

GC-Mass (calculated: 752.90 g / mol, measured: 752 g / mol)

[ Synthetic example  12] Synthesis of C-12

The procedure of Synthesis Example 11 was repeated except that 9- (4-bromophenyl) -9H-carbazole (8.56 g, 26.57 mmol) was used instead of 1-bromo-3,5-diphenylbenzene used in Synthesis Example 11 To obtain the desired compound C-12 (6.00 g, yield 59%).

GC-Mass (calculated: 765.90 g / mol, measured: 765 g / mol)

[ Synthetic example  13] Synthesis of C-13

IC-5 (6.32 g, 13.29 mmol) obtained in Preparation Example 5 was used instead of IC-1 used in Synthesis Example 1 and 3-bromo-1,1'-biphenyl (6.19 g, 26.57 mmol) was used instead of bromobenzene , The target compound C-13 (5.25 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 1.

GC-Mass (calculated: 627.73 g / mol, measured: 627 g / mol)

[ Synthetic example  14] Synthesis of C-14

([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] was used in place of 3-bromo- -4-amine (12.66 g, 26.57 mmol) was used in place of C-14 (8.57 g, yield 74%).

GC-Mass (theory: 871.04 g / mol, measured: 871 g / mol)

[ Synthetic example  15] Synthesis of C-15

IC-6 (8.52 g, 13.29 mmol) obtained in Preparation Example 6 was used in place of IC-1 used in Synthesis Example 1, and 4- (3-bromophenyl) -2,6-diphenylpyrimidine (10.29 g, 26.57 mmol ), The target compound C-15 (6.17 g, yield 49%) was obtained by carrying out the same procedure as in Synthesis Example 1.

GC-Mass (calculated: 947.09 g / mol, measured: 947 g / mol)

[ Synthetic example  16] Synthesis of C-16

The procedure of Synthesis Example 15 was repeated except that 2-bromonaphthalene (5.50 g, 26.57 mmol) was used instead of 4- (3-bromophenyl) -2,6-diphenylpyrimidine used in Synthesis Example 15, C-16 (7.03 g, yield 69%).

GC-Mass (calculated: 766.89 g / mol, measured: 766 g / mol)

[ Synthetic example  17] Synthesis of C-17

Bromo-9,9-dimethyl-9,10-dihydroacridine (7.66 g, 13.29 mmol) instead of bromobenzene was used instead of IC-7 (6.97 g, 13.29 mmol) obtained in Preparation Example 7 instead of IC- 26.57 mmol), the target compound C-15 (3.79 g, yield 39%) was obtained by carrying out the same procedure as in Synthesis Example 1.

GC-Mass (731.88 g / mol, measured: 731 g / mol)

[ Synthetic example  18] Synthesis of C-18

Except that 2-bromo-1,3,5-triazine (4.25 g, 26.57 mmol) was used instead of 10-bromo-9,9-dimethyl-9,10-dihydroacridine used in Synthesis Example 17, 17, the target compound C-18 (3.93 g, yield 49%) was obtained.

GC-Mass (theory: 603.67 g / mol, measurement: 603 g / mol)

[ Example  1] Green organic Field  Manufacturing of light emitting 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 electroluminescent device was produced as follows.

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was ultrasonically cleaned with distilled water. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, 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) / 90% compound C-1 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ 30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to prepare a green organic electroluminescent device.

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

[ Example  2 to 18]

The procedure of Example 1 was repeated, except that the compounds C-2 to C-18 synthesized in Synthesis Examples 2 to 18 were used instead of the compound C-1 used as a host material in the formation of the light emitting layer in Example 1 Thereby preparing a green organic electroluminescent device.

[ Comparative Example  One]

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound C-1 used as the host material of the light emitting layer in Example 1. The structure of CBP used is as follows.

[ Evaluation example  One]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices prepared in Examples 1 to 18 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

Host material The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 Compound C-1 6.50 517 42.0 Example 2 Compound C-2 6.55 519 42.1 Example 3 Compound C-3 6.50 519 42.0 Example 4 Compound C-4 6.50 517 42.3 Example 5 Compound C-5 6.55 516 41.8 Example 6 Compound C-6 6.60 518 42.1 Example 7 Compound C-7 6.50 518 42.0 Example 8 Compound C-8 6.55 519 41.5 Example 9 Compound C-9 6.55 517 42.0 Example 10 Compound C-10 6.60 517 41.8 Example 11 Compound C-11 6.59 517 41.7 Example 12 Compound C-12 6.45 518 42.1 Example 13 Compound C-13 6.50 520 42.0 Example 14 Compound C-14 6.60 519 41.6 Example 15 Compound C-15 6.60 519 41.6 Example 16 Compound C-16 6.50 517 41.7 Example 17 Compound C-17 6.55 521 41.9 Example 18 Compound C-18 6.50 522 42.0 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic electroluminescent devices (compounds C-1 to C-18) represented by formula (1) according to the present invention were used as the phosphorescent host material of the light- (Organic electroluminescent device of Comparative Example 1) using CBP as a material of the light emitting layer was superior to the organic electroluminescent device of Comparative Example 1 in current efficiency and drive voltage.

Claims (9)

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

In Formula 1,
_One of R ₁ and R ₂ , R ₂ and R ₃ , or R ₃ and R ₄ is a condensed ring represented by the following formula (2)
R ₁ to R ₅ are each independently hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, C An aryl group having ₆ to ₆₀ carbon atoms, 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 ~ C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C of the group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of the C ₆₀ group And an arylamine group of C ₆ to C ₆₀ ,
(2)

In Formula 2,
The dotted line means a site where condensation is performed with the compound of formula (1)
R ₆ to R ₉ each independently represent hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, C An aryl group having ₆ to ₆₀ carbon atoms, 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 ~ C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C of the group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of the C ₆₀ group And an arylamine group of C ₆ to C ₆₀ , wherein at least one is selected from the group consisting of:
(3)

In Formula 3,
L ₁ is a single bond, an arylene group having ₆ to ₆₀ carbon atoms, or a heteroarylene group having 5 to 60 nuclear atoms,
X ₁ Is selected from the group consisting of O, S, Se and NAr ₃ ,
Y ₁ And Y &lt; ₂ &gt; are each independently N or CR &lt; ₁₀ &
R ₁₀ and R ₂₁ to R ₂₄ each independently represent hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocyclic cycloalkyl group having 3 to 40 nuclear atoms An alkyl group, 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 aryl silyl group of _60, C ₂ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine of C ₆₀ pin oxide groups and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine, or, by combining groups of neighboring may form a condensed ring,
Ar ₁ to Ar ₃ are each independently a C ₆ to C ₁₈ aryl group or a heteroaryl group having 5 to 18 nuclear atoms,
The arylene group and the heteroarylene group of L ₁ , the Ar ₁ To Ar ₃ of the aryl group and heteroaryl group, the R ₁ to R ₁₀ and R ₂₁ to alkyl groups of R _24, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl A halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a cycloalkyl group, a nuclear atoms, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a heteroaryl of nuclear atoms of 5 to 60 aryl group, an alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ C ₁ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₂ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ an aryl phosphine group may be substituted with a C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ 1 or more selected from the group consisting of C ₆₀ arylamines. The method according to claim 1,
The compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (1a) to (1f):
[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

&Lt; RTI ID = 0.0 &

[Formula 1e]

(1f)

In the above general formulas (1a) to (1f)
Ar ₁ , Ar ₂ and R ₁ To R ₉ Is as defined in claim 1. The method according to claim 1,
(3) is selected from the group consisting of the structures represented by the following formulas (3a) to (3h):
[Chemical Formula 3]

(3b)

[Chemical Formula 3c]

(3d)

[Formula 3e]

(3f)

[Formula 3g]

[Chemical Formula 3h]

In the above formulas (3a) to (3h)
X ₁ , Y ₁ , Y _2, and R ₂₁ To R &lt; ₂₄ &gt; are as defined in claim 1,
X ₂ is selected from the group consisting of O, S, Se and NAr ₄ ,
Y ₃ And Y &lt; ₄ &gt; are each independently N or CR &lt; ₁₂ &
R ₁₂ and R ₂₅ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ heteroaryl in the alkyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 aryl group, C ₆ ~ C _A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ aryloxy group, group ₄₀ arylboronic of, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or the adjacent groups bonded to the condensed ring of Lt; / RTI &gt;
Ar ₄ is a C ₆ to C ₁₈ aryl group or a heteroaryl group having 5 to 18 nuclear atoms,
An aryl group, a heteroaryl group, the alkyl group of said R ₁₂ and R ₂₅ of the Ar _4, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group , An arylphosphine group, an arylphosphine oxide group and an arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocyclic cycloalkyl group having 3 to 40 nuclear atoms An alkyl group, 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 ₁ to C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₂ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine of C ₆₀ a pin oxide groups and at least one member selected from the group consisting of C ₆ ~ C ₆₀ aryl amine can be optionally substituted,
m is an integer of 0 to 4; The method according to claim 1,
And at least one of Ar ₁ to Ar ₃ is represented by the following formula (4).
[Chemical Formula 4]

In Formula 4,
A C ₆ to C ₁₈ arylene group or a heteroarylene group having 5 to 18 nuclear atoms,
Z ₁ to Z ₅ are each independently N or CR ₁₁ , wherein at least one of Z ₁ to Z ₅ is N,
R ₁₁ is hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₆ to C ₄₀ aryl, C ₃ to C ₄₀ cycloalkyl, heterocycloalkyl having 3 to 40 nuclear atoms, Nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl Or may be bonded to adjacent groups to form a condensed ring,
Alkyl groups of the L ₂ of the aryl group, a heteroaryl group, the R _11, an aryl group, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boronic group , Arylboron group, arylsilyl group, arylphosphine group and arylphosphine oxide group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, 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 ₁ to C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of. 5. The method of claim 4,
The compound of formula (4) is selected from the group consisting of the structures represented by the following A-1 to A-15:

In the above A-1 to A-15,
L ₂ and R ₁₁ are the same as defined in claim 4, wherein a plurality of R _{11 s} are the same or different from each other,
R ₂₆ is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ to C ₄₀ aryloxy group C C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C _An arylphosphine group having ₆ to ₄₀ carbon atoms, an arylphosphine oxide group having ₆ to ₄₀ carbon atoms, and an arylsilyl group having ₆ to ₄₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring,
Alkyl group of the R _26, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ of the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to the 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C in more than ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C selected from the group consisting of ₄₀ per arylsilyl more substituents may be substituted,
n is an integer of 0 to 4; The method of claim 4,
The L ₁ And L &lt; _{2 &gt;} are each independently a single bond or a phenylene group or a biphenylene group. 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 6. 8. The method of claim 7,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, and a light emitting layer. 8. The method of claim 7,
Wherein the organic compound layer containing the compound is a light emitting layer, and the compound is a phosphorescent host material.