KR101641411B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent device having improved properties such as luminous efficiency, driving voltage and lifetime by incorporating a novel phenazine-based compound having excellent hole injecting ability, hole transporting ability, and light emitting ability and the phenazine-based compound into an organic material layer .

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 Patent Publication No. 10-2011-0066763

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 each independently C (R ₈ ) or N, wherein when R ₈ is plural, they are the same or different;

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

The dotted line represents a moiety which is condensed with the formula (1)

Y ₁ is selected from the group consisting of N (Ar ₁ ), O, S, C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ );

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 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, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C 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 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, C group of ₁ to alkylboronic of C _40, 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 aryl amine Group, or may combine with adjacent groups 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 silyl groups, alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, each independently, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ 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 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.

The present invention also 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 one or more organic layers comprises a compound And an organic electroluminescent device.

Here, the one or more organic layers including the compound may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a light emitting layer, and may be a light emitting layer.

When the compound is included in the light emitting layer, it is preferably 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 compounds of the present invention are prepared by condensing a nitrogen-containing, heteroaromatic heteroaromatic ring moiety (e.g., pyrrole, imidazole, pyrazole, triazole) in a carbazole moiety to form a basic skeleton, A structure in which a (hetero) aromatic ring (for example, indene, indole, benzothiophene, benzofuran, benzoylol, etc.) is fused at the terminal to form a fused aromatic ring or a fused heterocyclic moiety Which is characterized by being represented by the above formula (1).

Since the compound of formula (1) according to the present invention contains a carbazole moiety having a wide band gap and a high triplet energy, the compound of the formula (1) has high triplet energy, is electrochemically stable, It is possible to prevent the formed excitons from migrating (spreading) to the surrounding organic material layer. In particular, the compound has higher triplet energy than dopants known in the art (e.g., Ir (ppy) ₃ , (piq) ₂ Ir (acac), etc.). Therefore, when the compound is used as a host of an organic electroluminescent device , The energy transferred to the dopant can be prevented from reversing to the host, and the luminous efficiency of the device can be improved.

In the compound of Formula 1, the carbazole moiety in the basic skeleton is excellent in hole transportability. Accordingly, the compound of Formula 1 may be applied to a hole injection layer and a hole transport layer. In addition, when various aromatic ring substituents, particularly an electron withdrawing group (EWG) having a high electron absorbing property, are introduced into such a basic skeleton, the compound of the present invention can be used as an electron withdrawing group, EWG) and the electron donating group (EDG), they become 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 to a host in a phosphorescent light-emitting layer.

In addition, the compound of the present invention is remarkably increased in molecular weight by bonding various substituents to the basic skeleton or condensing the substituents to form a fused aromatic ring or a fused heterocyclic moiety, (For example, CBP) because of its high glass transition temperature due to its high glass transition temperature.

When the compound of Formula 1 according to the present invention is used as a hole injection layer, a hole transporting layer, or a light emitting layer of the organic electroluminescent device, the durability, efficiency, and lifetime of the organic electroluminescent device are improved . 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 represented by Formula 1, X ₁ and X ₂ are each independently C (R ₈ ) or N, and when R ₈ is plural, they are the same as or different from each other.

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

More preferably, both X ₁ and X ₂ may be C (R ₈ ). Here, plural R < ₈ > 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 following 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). In another example, when R ₂ and R ₃ are bonded to each other to form a condensed ring represented by Formula 2, the compound may be represented by Formula 5 or 6 below. As another example, when R ₃ and R ₄ are bonded to each other to form a condensed ring represented by Formula 2, the compound may be represented by Formula 7 or 8 below.

In the above Formulas 3 to 8,

X ₁ , X ₂ , Y _1, and R ₁ to R ₁₂ are 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 is _{N (Ar 1), O,} S, C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) is selected from the group consisting of, preferably, N (Ar _1), O, and S, and more preferably N (Ar &_lt; ₁ >).

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 .

The aryl group, heteroaryl group and arylamine 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 alkynyl group, a C ₃ to C ₄₀ alkenyl group, ~ 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 ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a C ₆ ~ C _60, C ₆ - substituted at C ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and the group consisting of an aryl amine of the C ₆ ~ C ₆₀ of a first substituent at least one selected or is unsubstituted, is just plurality which the substituent They may be the same or different from each other.

R ₁ to R ₈ in which the condensed ring of Formula 2 is not formed and R ₉ to R ₁₂ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl , preferably 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 amine.

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 , Provided that when a plurality of the substituents are plural, they may be the same as or different from each other.

More preferably, in the 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 formula (2) is not formed are each independently hydrogen or the substituents S1 to S205 Can be selected from the group.

In Formula 1, Ar ₁ and at least one of R ₁ to R ₈ and R ₉ to R ₁₂ in which the condensed ring of Formula 2 is not formed may be a substituent represented by Formula 9 below.

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, Preferably at least one of Z ₁ to Z ₅ is N and the others are C (R ₁₃ ), wherein when R ₁₃ is plural, 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 phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₆₀ aryl amine, or of, or may be bonded to the adjacent groups can form a condensed ring,

Wherein the alkyl groups of the L-arylene group and a heteroarylene 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 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 of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of C ₆₀ arylamine Or unsubstituted and ring, it may be just when the plurality of substituents, these are the same or different from each other.

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 .

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

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

n is an integer of 0 to 4, and when n is 0, hydrogen is not substituted by substituent R ₂₁ ; when n is an integer of 1 to 4, R ₂₁ is deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C ₄₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ arylamine group of C _40, C ₁ ~ C ₄₀ alkylsilyl 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 ~ selected from the group consisting of C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl group in the silyl or, or in combination group to which they are adjacent, may form a condensed ring,

The alkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R ₂₁ each independently represent a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 hetero cycloalkyl group, C of 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 ₁ ~ 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 , provided that when the substituent is plural, they may be the same or different from each other.

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,

Ar ₁ and R ₁ to R ₁₂ are as defined in the above formula (1).

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.

In the present invention, aryl 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.

In the present invention, heteroaryl 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 is a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure can do. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

In the present invention, arylamine refers to an amine substituted with aryl having 6 to 40 carbon atoms.

In the present invention, cycloalkyl 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.

In the present invention, heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons, of the ring is N, O, S or Se Lt; / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, alkylsilyl is 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, the condensed rings refer to condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compound of formula (I) according to the present invention can be synthesized according to a general synthesis method. The compounds of formula (I) 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 provides an organic electroluminescent device including the compound represented by the above-mentioned formula (1).

Specifically, the present invention includes a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes the compound represented by Formula 1. At this time, the compounds represented by Formula 1 may be used alone or in combination of two or more.

The at least one organic material layer includes 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 organic material layer includes the compound represented by Formula 1, . In particular, when the compound represented by Formula 1 is included in the organic electroluminescent device as a light emitting layer material, the luminous efficiency, brightness, power efficiency, thermal stability, and device lifetime of the organic electroluminescent device can be improved.

For example, the compound represented by Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, and may preferably be a phosphorescent host of the light emitting layer.

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 .

According to an example, 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 stacked on a substrate. Alternatively, the electron injection layer may be located on the electron transporting layer. At least one of the hole injecting layer, the hole transporting layer, and the light emitting layer may include the compound represented by the above formula (1).

The organic electroluminescent device of the present invention may be formed by using materials and methods known in the art, except that at least one of the one or more organic layers (for example, the light emitting layer) includes the compound represented by Formula 1 Thereby forming 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.

Examples of substrates usable in the present invention include silicon wafers, quartz or glass plates, metal plates, plastic films and sheets, but are 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 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 1] Synthesis of Core 1 and Core 2

<Step 1> Synthesis of 1- (2-bromo-4-chlorophenyl) -1H-indole

4-chloro-1-iodobenzene (54.1 g, 170.72 mmol), Cu powder (1.08 g, 17.07 mmol), K ₂ CO ₃ (47.19 g, , 341.44 mmol), and nitrobenzene (200 ml) were mixed and stirred at 250 ° C for 12 hours.

After termination of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed, and the residue was purified by column chromatography to give 1- (2-bromo-4-chlorophenyl) -1H-indole (40.3 g, yield 77%).

^{1 H-NMR: δ 6.52 (} d, 1H), 6.87 (t, 1H), 7.32 (t, 1H), 7.45 (m, 2H), 7.60 (d, 1H), 7.82 (s, 1H), 7.94 ( m, 2H)

<Step 2> Synthesis of 9-chloropyrrolo [3,2,1-jk] carbazole

1-indole (40.3 g, 131.45 mmol), Pd (OAc) ₂ (4.41 g, 15 mol%), K ₂ CO ₃ (90.8 g, 657.25 mmol), BnEt ₃ NCl (29.9 g, 131.45 mmol), PPh ₃ (12.06 g, 35 mol%) and DMA (500 ml) were mixed and stirred at 100 ° C for 6 hours.

After termination of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and then 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 9-chloropyrrolo [3,2,1-jk] carbazole (19.8 g, yield 67%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.09 (d, 1H), 7.29 (m, 2H), 7.58 (m, 3H), 8.12 (d, 1H)

<Step 3> Synthesis of 9- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole

Chloropyrrolo [3,2,1-jk] carbazole (19.8 g, 87.73 mmol), 2-nitrophenylboronic acid (16.1 g, 96.50 mmol) and X-phos (4.18 g, Pd (OAc) ₂ (0.98 g, 5 mol%) was added to a mixture of Cs ₂ CO ₃ (57.16 g, 175.46 mmol) and Tol / EtOH / H ₂ O (250 ml / 120 ml / 120 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 MgSO ₄ was added thereto, followed by filtration. The solvent was removed from the obtained organic layer and then purified by column chromatography to obtain 9- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole (21.3 g, yield 78%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (m, 2H), 7.77 (m, 4H), 7.90 (m, 2H), 8.08 (m, 3H)

<Step 4> Synthesis of Core 1 and Core 2

(21.3 g, 68.19 mmol), triphenylphosphine (53.6 g, 204.59 mmol) and 1,2-dichlorobenzene (180 ml, ) Were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, and an organic layer was extracted with dichloromethane. Water was removed from the obtained organic layer with MgSO ₄ and purified by column chromatography to obtain Core 1 (7.64 g, yield 40%) and Core 2 (6.1 g, yield 32%).

¹ H-NMR of the Core 1: δ 6.42 (d, 1H), 7.31 (m, 3H), 7.50 (t, 1H), 7.65 (m, 4H), 8.12 (m, 2H), 11.12 (s, 1H)

¹ H-NMR of Core 2: δ 6.45 (d, 1H), 7.27 (m, 3H), 7.40 (s, 1H), 7.55 (m, 2H), 7.63 (m, 2H), 8.15 (m, 2H) , 11.18 (s, 1 H)

[Preparation Example 2] Synthesis of Core 3 and Core 4

<Step 1> Synthesis of 1- (2-bromo-5-chlorophenyl) -1H-indole

Except that 1-bromo-4-chloro-2-iodobenzene (54.1 g, 170.72 mmol) was used in place of 2-bromo-4-chloro-1-iodobenzene used in Step 1 of Preparation Example 1, (2-bromo-5-chlorophenyl) -1H-indole (37.6 g, yield 72%) was obtained in the same manner as in <Step 1> of Example 1.

^{1 H-NMR: δ 6.52 (} d, 1H), 6.87 (t, 1H), 7.36 (m, 2H), 7.59 (m, 2H), 7.70 (s, 1H), 7.95 (m, 2H)

<Step 2> Synthesis of 8-chloropyrrolo [3,2,1-jk] carbazole

(2-bromo-5-chlorophenyl) -1 H-indole obtained in Step 1 of Preparation Example 2 was used instead of 1- (2-bromo-4-chlorophenyl) chloropyrrolo [3,2,1-jk] carbazole (19.0 g, 122.6 mmol) was obtained by carrying out the same procedure as <Step 2> of Preparation Example 1, Yield: 69%).

^{1 H-NMR: δ 6.42 (} d, 1H), 7.01 (d, 1H), 7.28 (m, 2H), 7.41 (s, 1H), 7.65 (d, 1H), 8.12 (m, 2H)

<Step 3> Synthesis of 8- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole

Chloropyrrolo [3,2,1-jk] carbazole (19.0 g, 0.35 mmol) was used in Step 2 of Preparation Example 2 instead of 9-chloropyrrolo [3,2,1-jk] carbazole used in Step 3 of Preparation Example 1 , 84.19 mmol), the target compound, 8- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole (19.4 g, , Yield: 74%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.30 (m, 2H), 7.68 (m, 3H), 7.81 (d, 1H), 7.92 (t, 1H), 8.15 (m, 4H), 8.41 ( d, 1 H)

<Step 4> Synthesis of Core3 and Core4

(2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole in Step 3 of Preparation Example 2 instead of 9- (2-nitrophenyl) pyrrolo [ The procedure of Step 4 of Preparation Example 1 was repeated to obtain the target compound Core 3 (7.1 g, yield 41%), except that 2,1-jk] carbazole (19.4 g, 62.11 mmol) And Core 4 (5.4 g, 31% yield).

¹ H-NMR:? 6.42 (d, 1H), 7.27 (m, 3H), 7.58 (m, 4H), 7.11

¹ H-NMR of the Core 4: δ 6.43 (d, 1H), 7.30 (m, 3H), 7.42 (s, 1H), 7.55 (m, 2H), 7.65 (m, 2H), 8.15 (m, 2H) , 11.18 (s, 1 H)

[Preparation Example 3] Synthesis of Core 5

<Step 1> Synthesis of 1- (2,6-dibromophenyl) -1H-indole

Except that 1,3-dibromo-2-iodobenzene (61.7 g, 170.72 mmol) was used instead of 2-bromo-4-chloro-1-iodobenzene in Step 1 of Preparation Example 1, (2,6-dibromophenyl) -1H-indole (43.1 g, yield 72%) was obtained by carrying out the same processes as in Step 1].

^{1 H-NMR: δ 6.52 (} d, 1H), 6.88 (m, 2H), 7.33 (t, 1H), 7.58 (m, 3H), 7.92 (m, 2H)

<Step 2> Synthesis of 7-bromopyrrolo [3,2,1-jk] carbazole

(2,6-dibromophenyl) -1H-indole obtained in Step 1 of Preparation Example 3 was used instead of 1- (2-bromo-4-chlorophenyl) The same procedure as in <Step 2> of Preparation Example 1 was conducted except that the compound (43.1 g, 122.7 mmol) was used in place of 7-bromopyrrolo [3,2,1-jk] carbazole 63%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.25 (m, 3H), 7.42 (d, 1H), 7.65 (d, 1H), 8.08 (m, 2H)

<Step 3> Synthesis of 7- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole

Bromopyrrolo [3,2,1-jk] carbazole (obtained in Step 2 of Preparation Example 3 instead of 9-chloropyrrolo [3,2,1-jk] carbazole used in Step 3 of Preparation Example 1 (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole (18.1 g, 77.35 mmol) was obtained by carrying out the same procedure as <Step 3> of Preparation Example 1, g, yield: 75%).

^{1 H-NMR: δ 6.43 (} d, 1H), 7.32 (m, 3H), 7.67 (m, 2H), 7.90 (m, 3H), 8.08 (m, 3H)

<Step 4> Synthesis of Core 5

(2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole obtained in Step 3 of Preparation Example 3 was used instead of 9- (2-nitrophenyl) pyrrolo [ , 8.9 g (yield: 55%) was obtained by carrying out the same procedure as <Step 4> of Preparation Example 1, except that 2,1-jk] carbazole (18.1 g, 58.01 mmol) .

^{1 H-NMR: δ 6.46 (} d, 1H), 7.25 (m, 4H), 7.50 (t, 1H), 7.65 (m, 2H), 8.15 (m, 3H), 11.15 (s, 1H)

[Synthesis Example 1] Synthesis of Inv 91

(3.0 g, 10.70 mmol), 2- (4-chlorophenyl) -4-phenylpyrimidine (3.42 g, 12.84 mmol) and Pd (OAc) ₂ (0.12 g, 0.53 mmol) synthesized in Preparation Example 1 under a nitrogen stream. (3.08 g, 32.1 mmol), P (t-bu) ₃ (0.43 g, 2.14 mmol) and Toluene (80 ml) were mixed and stirred at 110 ° C for 12 hours.

After the reaction was completed, the organic layer was extracted with ethyl acetate, and then water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain the desired compound Inv 91 (3.3 g, yield 62%).

GC-Mass (calculated: 510.59 g / mol, measured: 510 g / mol)

[Synthesis Example 2] Synthesis of Inv 106

(3.0 g, 10.70 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.43 g, 12.84 mmol) synthesized in Preparation Example 1, NaH mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After completion of the reaction, water was added thereto, and the solid product was filtered, and then purified by column chromatography to obtain the target compound, Inv 106 (3.8 g, yield 68%).

GC-Mass (calculated: 511.57 g / mol, measured: 511 g / mol)

[Synthesis Example 3] Synthesis of Inv 107

The procedure of Synthesis Example 1 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.42 g, 12.84 mmol) was used instead of 2- (4-chlorophenyl) -4-phenylpyrimidine used in Synthesis Example 1 To obtain Inv 107 (3.5 g, yield 65%) as a target compound.

GC-Mass (calculated: 510.59 g / mol, measured: 510 g / mol)

[Synthesis Example 4] Synthesis of Inv 141

Except that 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (4.4 g, 12.84 mmol) was used instead of 2- (4-chlorophenyl) -4-phenylpyrimidine used in Synthesis Example 1, The same procedure was carried out to obtain Inv 141 (3.8 g, yield 61%) as a target compound

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 5] Synthesis of Inv 168

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.41 g, 12.84 mmol) was used instead of 2- (4-chlorophenyl) -4-phenylpyrimidine used in Synthesis Example 1 , Inv 168 (4.1 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 1.

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[Synthesis Example 6] Synthesis of Inv 230

Instead of Core 1 used in Synthesis Example 1, Core 2 (3 g, 10.70 mmol) synthesized in Preparation Example 1 was used and 4-chloro-2,6-diphenylpyrimidine (3.42 g, 12.84 mmol), the title compound, Inv 230 (3.4 g, yield 63%) was obtained in the same manner as in Synthesis Example 1.

GC-Mass (calculated: 510.59 g / mol, measured: 510 g / mol)

[Synthesis Example 7] Synthesis of Inv 244

(3.0 g, 10.70 mmol) synthesized in Preparation Example 2 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (5.9 g, 12.84 mmol ), Cu powder (0.34 g, 5.35 mmol), K ₂ CO ₃ (2.22 g, 16.05 mmol) and nitrobenzene (80 ml) were mixed and stirred at 190 ° C for 12 hours.

After the reaction was terminated, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and then the water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound, Inv 244 (4.8 g, yield 69%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[Synthesis Example 8] Synthesis of Inv 266

(Biphenyl-3-yl) -2 (4-chlorophenyl) -4-phenylpyrimidine was used instead of Core 1 used in Synthesis Example 1, (3.3 g, yield: 61%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that -chloropyrimidine (3.42 g, 12.84 mmol) was used.

GC-Mass (calculated: 510.59 g / mol, measured: 510 g / mol)

[Synthesis Example 9] Synthesis of Inv 269

Core 3 (3 g, 10.70 mmol) synthesized in Preparation Example 2 was used instead of Core 2 used in Synthesis Example 7, and 2- (5-bromobiphenyl-3-yl) Inv 269 (3.6 g, yield 67%) was obtained by carrying out the same procedure as in Synthesis Example 7, except that 2-bromo-4,6-diphenylpyridine (3.9 g, 12.84 mmol) .

GC-Mass (calculated: 509.6 g / mol, measured: 509 g / mol)

[Synthesis Example 10] Synthesis of Inv 278

Except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.4 g, 12.84 mmol) was used instead of 4- (biphenyl-3-yl) -2-chloropyrimidine used in Synthesis Example 8, 8, the desired compound Inv 278 (4.0 g, yield 64%) was obtained.

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 11] Synthesis of Inv 282

Instead of 2- (4-bromophenyl) -4,6-diphenyl-1,3,4,5-triazine used in Synthesis Example 7 instead of 2- (5-bromobiphenyl- 5-triazine (4.98 g, 12.84 mmol) was used in place of 4-bromo-4-methoxybenzaldehyde, to obtain the title compound Inv 282 (4.2 g, yield 62%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[Synthesis Example 12] Synthesis of Inv 361

Except that Core 5 (3 g, 10.70 mmol) synthesized in Preparation Example 3 was used instead of Core 2 used in Synthesis Example 7 and 2- (5-bromobiphenyl-3-yl) Inv 361 (3.6 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 7, except that 2-bromo-4,6-diphenylpyrimidine (3.99 g, 12.84 mmol) .

GC-Mass (calculated: 510.59 g / mol, measured: 510 g / mol)

[Synthesis Example 13] Synthesis of Inv 366

Instead of Core 1 used in Synthesis Example 1, Core 5 (3 g, 10.70 mmol) synthesized in Preparation Example 3 was used instead of 4- (3-chlorophenyl) -2,6 The procedure of Synthesis Example 1 was repeated except that -diphenylpyrimidine (4.4 g, 12.84 mmol) was used to obtain Inv 366 (3.8 g, yield 61%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 14] Synthesis of Inv 212

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4-phenylquinazoline (3.08 g, 12.84 mmol) was used instead of 2- (4-chlorophenyl) -4-phenylpyrimidine used in Synthesis Example 1, Compound 212 (2.9 g, yield 57%) was obtained.

GC-Mass (calculated: 484.55 g / mol, measured: 484 g / mol)

[Synthesis Example 15] Synthesis of Inv 293

2-chloro-4- (4- (naphthalen-2-yl) phenyl) quinazoline (4.69 g, 12.84 mmol) instead of 4- (biphenyl-3-yl) -2-chloropyrimidine used in Synthesis Example 8 , The target compound Inv 293 (3.2 g, yield 50%) was obtained by carrying out the same procedure as in Synthesis Example 8.

GC-Mass (calculated: 610.7 g / mol, measured: 610 g / mol)

[Synthesis Example 16] Synthesis of Inv 383

Except that 4- (biphenyl-4-yl) -2-chloroquinazoline (4.05 g, 12.84 mmol) was used instead of 4- (3-chlorophenyl) -2,6-diphenylpyrimidine used in Synthesis Example 13 13, the target compound Inv 383 (3.4 g, yield: 58%) was obtained.

GC-Mass (calculated: 560.65 g / mol, measured: 560 g / mol)

[Example 1] Production of green organic EL device

The compound Inv-91 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) / compound Inv-91 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order to form an organic EL device.

At this time, the structures of m-MTDATA, TCTA, Ir (ppy) ₃ , and BCP used are as follows.

[ Example  2] to [ Example  13] Green organic EL  Device fabrication

A green organic EL device was prepared in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound Inv-91 used as a luminescent 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 instead of the compound Inv-91 used as a luminescent host material in the formation of the light emitting layer. The structure of CBP used is as follows.

[Evaluation Example 1]

The green organic EL devices fabricated in Examples 1 to 13 and Comparative Example 1 were measured for driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2, and the results are shown in Table 1 below.

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 Inv-91 6.54 516 39.9 Example 2 Inv-106 6.59 516 41.2 Example 3 Inv-107 6.63 515 44.3 Example 4 Inv-141 6.71 516 41.5 Example 5 Inv-168 6.62 515 45.6 Example 6 Inv-230 6.57 517 43.4 Example 7 Inv-244 6.68 516 45.3 Example 8 Inv-266 6.70 516 42.3 Example 9 Inv-269 6.49 515 43.4 Example 10 Inv-278 6.61 517 45.5 Example 11 Inv-282 6.59 517 43.6 Example 12 Inv-361 6.63 516 42.7 Example 13 Inv-366 6.62 515 41.7 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL devices of Examples 1 to 13 using the compounds (Inv-91 to Inv-366) according to the present invention as light emitting layer materials were the same as the green organic EL devices of Comparative Example 1 using CBP It was found that the current efficiency and the driving voltage were superior to each other.

[Example 14] Preparation of red organic EL device

The compound Inv 212 synthesized in Synthesis Example 14 was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent 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) / Compound Inv-212 + 10% (piq) ₂ Ir (acac) (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) on the prepared ITO transparent electrode ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

At this time, the structures of m-MTDATA, TCTA and BCP used are as described in Example 1, and the structure of (piq) ₂ Ir (acac) is as follows.

[ Example  15] to [ Example  16] Red organic EL  Device fabrication

A red organic EL device was manufactured in the same manner as in Example 14, except that the compounds shown in the following Table 2 were used instead of the compound Inv 212 used as a luminescent host material in Example 14.

[ Comparative Example  2] Red organic EL  Device fabrication

A red organic electroluminescent device was fabricated in the same manner as in Example 14, except that CBP was used in place of Inv-212 used as a luminescent host material in the formation of the light emitting layer.

At this time, the structure of the CBP used is as described in Comparative Example 1.

[ Evaluation example  2]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices fabricated in Examples 14 to 16 and Comparative Example 2, respectively, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 14 Inv-212 4.68 12.8 Example 15 Inv-293 4.69 13.1 Example 16 Inv-383 4.73 12.6 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2 above, the red organic EL devices of Examples 14 to 16 using the compounds (Inv 212 to Inv 383) according to the present invention as light emitting layer materials were the same as the red organic EL devices of Comparative Example 2 using CBP It was found that the current efficiency and the driving voltage were superior to each other.

Claims (11)

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

In Formula 1,
X ₁ and X ₂ are each independently C (R ₈ ), wherein when R ₈ is plural, they are the same or different from each other;
R ₁ and R ₂ , R ₂ and R _3, and any one of R ₃ and R ₄ are combined to form a condensed ring represented by the following formula (2);
(2)

The dotted line is a moiety that is condensed with Formula 1;
Y ₁ is N (Ar ₁ );
Ar ₁ is selected from the group consisting of phenyl and heteroaryl groups having 6 to 10 nucleus atoms containing 1 to 3 N;
R ₁ to R ₄ and R ₅ to R ₁₂ in which the condensed ring of Formula 2 is not formed are each independently hydrogen;
The phenyl and heteroaryl groups of Ar ₁ are each independently substituted with at least one substituent selected from the group consisting of C ₆ to C ₁₂ aryl groups and heteroaryl groups having 6 to 18 nucleus atoms containing 2 or 3 N atoms Provided that when the substituent is plural, they may be the same or different. 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), (4), (6)
(3)

[Chemical Formula 4]

[Chemical Formula 6]

(7)

In the above formulas (3), (4), (6) and (7)
X ₁ , X ₂ , Y ₁ and R ₁ to R ₁₂ are as defined in claim 1, respectively. delete delete delete delete The method according to claim 1,
And Ar &lt; ₁ &gt; is a substituent represented by the following formula (9).
[Chemical Formula 9]

In the above formula (9)
L is a single bond or a C ₆ to C ₁₂ arylene group;
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 and C ₆ ~ C ₁₂ aryl group, each independently;
The aryl group of R &lt; ₁₃ &gt; is each independently substituted or unsubstituted with an aryl group of C &lt; _{10 &} gt ;, provided that when the substituents are plural, they may be the same or different. The method according to claim 1,
Ar ₁ is selected from the group consisting of substituents represented by the following formulas A-1, A-4, A-6, A-9, and A-10.

In Formulas A-1, A-4, A-6, A-9 and A-10,
L is a single bond or a C ₆ to C ₁₂ arylene group;
R ₁₃ are the same or different and are each independently selected from the group consisting of hydrogen and C ₆ -C ₁₂ aryl groups;
The aryl group of R &lt; ₁₃ &gt; may each independently be substituted or unsubstituted with an aryl group of C &lt; ₁₀ &gt;;
n is an integer of 1 to 4, and R &lt; ₂₁ &gt; are each independently hydrogen. 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, 2, 7, and 8. 10. The method of claim 9,
Wherein at least one organic material 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,
Wherein the compound in the light emitting layer is a phosphorescent host.