WO2015012528A2 - Organic compound and organic electroluminescent element comprising same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent element comprising the same. The compound according to the present invention can improve luminance efficiency, driving voltage, lifespan, and the like of an electroluminescent element by being used in an organic material layer, preferably a light emitting layer, of the organic electroluminescent element.

Description

Organic compound and organic electroluminescent device comprising the same

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

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. The material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. In addition, in order to increase luminous efficiency through increasing color purity and energy transfer, a host / dopant system may be used as the light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the development of the phosphor can theoretically improve the luminous efficiency up to four times as compared to the fluorescent material, attention has been focused on not only the phosphorescent dopant material but also the phosphorescent host material.

To date hole injection materials, hole transport materials. NPB, BCP, Alq ₃ and the like are known as hole blocking materials and electron transporting materials, and anthracene derivatives are known as fluorescent dopant / host materials among light emitting materials. In addition, as a phosphorescent dopant material which has an advantage in terms of efficiency improvement among light emitting materials, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ are known. CBP is known.

However, the conventional light emitting materials are good in terms of the light emission characteristics, but because the glass transition temperature is low, the thermal stability is not very good, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, there is a demand for development of a light emitting material having excellent performance.

An object of the present invention is to provide a novel organic compound excellent in light emitting ability, hole transporting ability and hole injection ability.

In addition, the present invention is the novel organic It is another object of the present invention to provide an organic electroluminescent device including a compound having a low driving voltage, high luminous efficiency, and an improved lifetime.

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

[Formula 1]

In Formula 1, one of R ₁ and R ₂ , R ₂ and R ₃ , or R ₃ and R ₄ forms a condensed ring represented by the following Formula 2, R ₁ to R ₅ which do not form a condensed ring is Each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ aryl of C ₆₀ silyl group, 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 oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ Is selected from the group consisting of arylamine groups,

[Formula 2]

In Chemical Formula 2, a dotted line means a site where condensation occurs with the compound of Chemical Formula 1, R ₆ to R ₉ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear hetero atoms 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C _{60 It} is selected from the group consisting of an arylamine group, wherein at least one of R ₆ to R ₉ is 3,

[Formula 3]

In Chemical Formula 3, * means a site bonded to Chemical Formula 2,

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 ₂ are each independently N or CR ₁₀ ,

R ₁₀ and R ₂₁ to R ₂₄ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, and nuclear atom 3 to 40 heterocyclo Alkyl group, C ₆ ~ C ₆₀ Aryl group, Nuclear 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl Group, C ₆ ~ C ₆₀ arylsilyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl force It may be selected from the group consisting of a pin oxide group and an arylamine group of C ₆ ~ C ₆₀ , or may be combined with adjacent groups to form a condensed ring,

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

The arylene group and heteroarylene group of L _1, the aryl group and heteroaryl group of Ar ₁ to Ar ₃ , the alkyl group, cycloalkyl group, heterocycloalkyl group, and aryl group of R ₁ to R ₁₀ and R ₂₁ to R ₂₄ . , Heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyan Furnace group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₂ ~ C ₄₀ alkyl boron group, aryl of C ₆ ~ C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of the group consisting of an aryl amine By standing or more substituents selected one species may be substituted. In this case, when substituted with a plurality of substituents, a plurality of substituents may be the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device characterized in that it comprises.

At least one organic material layer including the compound represented by Chemical Formula 1 is selected from the group consisting of a hole transporting layer, a hole injection layer and a light emitting layer, preferably a hole transporting layer and / or a light emitting layer, more preferably a light emitting layer.

The compound represented by Chemical Formula 1 may be a phosphorescent host of the emission layer.

Meanwhile, 'alkyl' used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Non-limiting 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 straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms 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 or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Non-limiting examples thereof include ethynyl, 2-propynyl and the like.

As used herein, 'cycloalkyl' 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' as used herein 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 preferably at least one carbon in the ring, preferably 1 to 3 carbons are substituted with a hetero atom 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 a single ring or a C 6-60 aromatic hydrocarbon in which two or more rings are combined. In this case, the two or more rings may be attached in a simple or condensed form with each other. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.

'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, and at least one carbon in the ring, preferably 1 To 3 carbons are substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). In this case, the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

'Alkoxyoxy' used in the present invention means a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. It may include. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

'Aryloxy' used in the present invention means a monovalent functional group represented by R'O-, wherein R 'is an 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, and arylamine has 6 to 60 carbon atoms. Amine substituted with aryl.

As used herein, the term 'condensed ring' refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated.

1. New Compound

The novel organic compound according to the present invention is an indole-based moiety at the end of a pyrazolocarbazole moiety condensed with an indazole-based moiety and an indole-based moiety. ) And an indole-based moiety condensed pyrazolocarbazole-based moiety is directly bonded or by a linking group (e.g. arylene group, etc.) to form a basic skeleton, As a structure in which a variety of substituents are bonded, it is characterized in that represented by the formula (1).

The compound represented by the formula (1) has a higher molecular weight than the material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')) applied to the conventional organic electroluminescent device has a high glass transition temperature, thermal stability great.

Meanwhile, among the organic material layers included in the organic EL device, the host material included in the phosphorescent layer should have a triplet energy gap of the host higher than that of the dopant material. In other words, in order to effectively provide phosphorescence from the dopant material, the lowest excited state of the host material must be higher in energy than the lowest emission state of the dopant material. In the compound represented by Formula 1, energy levels may be effectively controlled by introducing various substituents into condensed pyrazolocarbazole moieties having a wide singlet energy level and a high triplet energy level. In addition, the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer.

In addition, the compound represented by Chemical Formula 1 has a structure in which an electron withdrawal group (EWG) having high electron absorbing property is coupled, and thus the binding force between holes and electrons can be enhanced because the whole molecule has a bipolar characteristic.

As such, the compound represented by Chemical Formula 1 may improve the phosphorescence property of the organic EL device and improve hole injection / transport ability, emission efficiency, driving voltage, lifetime characteristics, and the like. Accordingly, the electron transport ability and the like can also be improved. Accordingly, the compound represented by Chemical Formula 1 according to the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), a hole transport layer material and a hole injection layer material Can be used.

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

[Formula 1a]

[Formula 1b]

[Formula 1c]

[Formula 1d]

[Formula 1e]

[Formula 1f]

Ar ₁ , Ar ₂ and R ₁ to R ₉ in Chemical Formulas 1a to 1f are as defined in Chemical Formula 1. At least one of R ₆ to R ₉ is represented by Chemical Formula 3, and R ₈ is particularly preferably represented by Chemical Formula 3.

Meanwhile, in Chemical Formula 3, L ₁ is preferably linked to R ₂₃ in R ₂₁ to R ₂₄ . Specifically, Formula 3 is preferably selected from the group consisting of structures represented by the following Formulas 3a to 3h.

[Formula 3a]

[Formula 3b]

[Formula 3c]

[Formula 3d]

[Formula 3e]

[Formula 3f]

[Formula 3g]

[Formula 3h]

X ₁ , Y ₁ , Y ₂ and R ₂₁ to R ₂₄ in Chemical Formulas 3a to 3h are the same as defined in Chemical Formula 3. At this time, X ₁ is preferably NAr ₃ , X ₂ is selected from the group consisting of O, S, Se and NAr ₄ , and among them, NAr ₄ is preferred.

And Y ₃ and Y ₄ are each independently N or CR ₁₂ , wherein Y ₃ and Y ₄ are both If CR _12, a plurality of CR ₁₂ may be the same or different from each other.

R ₁₂ and R ₂₅ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to 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 an aryl group having ₆ to ₁₈ carbon atoms or a heteroaryl group having 5 to 18 nuclear atoms, and m is an integer of 0 to 4.

Meanwhile, the aryl group and heteroaryl group of Ar ₄ , the alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkyl boron group and aryl boron of R ₁₂ and R ₂₅ . The group, the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 hetero Cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₅ ~ C ₆₀ heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyl Silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl It may be substituted with one or more substituents selected from the group consisting of a phosphine oxide group and a C ₆ ~ C ₆₀ arylamine group. Specifically, it is preferably substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and heteroaryl group of 5 to 60 nuclear atoms. . In this case, when substituted with a plurality of substituents, a plurality of substituents may be the same or different from each other.

In Formulas 1, 2, and 3, Ar ₁ to Ar ₃ are each independently an aryl group having ₆ to ₁₈ carbon atoms or a heteroaryl group having 5 to 18 nuclear atoms, wherein at least one is represented by the following Formula 4 desirable.

[Formula 4]

In Chemical Formula 4, * means a site bonded to Chemical Formulas 1,2 and 3, L ₂ is a single bond, an arylene group having ₆ to ₁₈ carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms, and Z is 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 group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of 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 May be selected from the group consisting of groups, or may combine with adjacent groups to form a condensed ring,

An arylene group, a heteroarylene group of L ₂ , an alkyl group, 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 boron group of the above R ₁₁ . , Aryl boron group, aryl silyl group, aryl phosphine group and aryl phosphine oxide group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide group, and a C ₆ ~ least one member selected from the group consisting of an aryl amine of the C ₆₀ substituent of ₆₀ can be replaced. In this case, when substituted with a plurality of substituents, a plurality of substituents may be the same or different from each other.

The formula 4 is more preferably selected from the group consisting of the structures represented by A-1 to A-15.

In the above A-1 to A-15,

L ₂ and R ₁₁ are the same as defined in Formula 4, wherein a plurality of R ₁₁ is the same as or different from each other,

R ₂₆ is hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₁ ~ C ₄₀ groups of the alkyl silyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of a silyl or, by combining groups of adjacent, may form a condensed ring,

n is an integer of 0-4.

Wherein the alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylsilyl of R ₂₆ The groups are each independently 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 aryl group, nuclear atom 5 To 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom number 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. In this case, when substituted with a plurality of substituents, a plurality of substituents may be the same or different from each other.

On the other hand, Ar ₁ to Ar ₃ that is not represented by the general formula (4) is a C ₆ ~ C ₁₈ aryl group or a heteroaryl group of 5 to 18 nuclear atoms, and among these, a phenyl group, acridine group, or 1,3 It is more preferable that it is a, 5-triazine group.

In addition, in Chemical Formulas 3 and 4, L ₁ and L ₂ are each independently a single bond, or preferably a phenylene group or a biphenylene group.

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

2. Organic electroluminescent device

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

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound represented by Formula 1 may be used alone or in combination of two or more.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein the organic material layer containing the compound represented by the formula (1) is preferably a light emitting layer.

The emission layer of the organic electroluminescent device according to the present invention may include a host material, and may include a compound represented by Chemical Formula 1 as the host material. When the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer increases, so the efficiency (luminescence efficiency and power efficiency) of the organic electroluminescent device is increased. ), Lifespan, brightness and driving voltage can be improved.

The structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer may include a compound represented by the formula (1). have. In this case, the compound of the present invention may be used as a phosphorescent host material of the emission layer. Meanwhile, the electron injection layer may be further stacked on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material 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 and a sheet, but is not limited thereto.

The anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

Preparation Example 1 Synthesis of IC-1

<Step 1> Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole

5-bromo-1H-indazole (25.22 g, 0.128 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3) under nitrogen stream , 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 1,4-dioxane (500 ml) were mixed and 130 ° C Stir at 12 h.

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

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

4-chloro-2-iodo-1-nitrobenzene (21.37 g, 75.41 mmol) under nitrogen stream 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) were mixed and then Pd (PPh ₃ ) at 40 ° C. ₄ (4.36 g, 5 mol%) was added and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give 5- (5-chloro-2-nitrophenyl) -1H-indazole (15.60 g, yield 63%). Got.

¹ H-NMR: δ 7.63 (d, 1H), 7.71 (d, 1H), 8.07 (s, 1H), 8.20 (s, 1H), 8.26 (m, 2H), 8.38 (d, 1H), 12.24 ( s, 1 H)

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

5- (5-chloro-2-nitrophenyl) -1H-indazole (12.63 g, 46.17 mmol), iodobenzene (14.13 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol) obtained in the <Step 2> under a nitrogen stream. ), 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, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer, and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indazole ( 11.46 g, yield 71%) was obtained.

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

5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indazole (5.56 g, 15.91 mmol), Triphenylphosphine (10.43 g, 39.77 mmol) and 1,2- obtained in <Step 3> under a nitrogen stream. dichlorobenzene (50 ml) was mixed and stirred for 12 hours.

After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The obtained organic layer was removed with MgSO _4, and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 7-chloro-3-phenyl-3,10-dihydropyrazolo [4,3- a] carbazole (2.68 g, yield 53%) was obtained.

^{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 Synthesis of IC-1

9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (2.59 g, 7.03 mmol) under nitrogen stream and in <Step 4> Obtained 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 ) Was mixed, and then Pd (PPh ₃ ) ₄ (0.48 g, 5 mol%) was added at 40 ° C., and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain IC-1 (1.77 g, 66% yield).

¹ H-NMR: δ 7.50 (m, 17H), 7.88 (m, 3H), 8.34 (m, 2H), 8.55 (d, 1H), 10.11 (s, 1H)

Preparation Example 2 Synthesis of IC-2

9-phenyl-2 instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole used in <Step 4> of Preparation Example 1 <Step 4 of Preparation Example 1, except that-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (2.59 g, 7.03 mmol) was used. Compound IC-2 was obtained by following the same procedure as>.

¹ H-NMR: δ 7.44 (m, 15H), 7.80 (m, 4H), 8.18 (d, 1H), 8.33 (m, 2H), 8.55 (d, 1H), 10.10 (s, 1H)

Preparation Example 3 Synthesis of IC-3

1-phenyl-5 instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole used in <Step 4> of Preparation Example 1 <Step 4 of Preparation Example 1, except that-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (2.25 g, 7.03 mmol) was used. Compound IC-3 was obtained by following the same procedure as>.

¹ H-NMR: δ 7.42 (m, 3H), 7.61 (m, 10H), 7.78 (s, 1H), 7.87 (d, 1H), 8.10 (s, 1H), 8.35 (m, 4H), 10.08 ( s, 1 H)

Preparation Example 4 Synthesis of IC-4

<Step 1> 7-chloro-3,10- diphenyl-3,10-dihydropyrazolo [4,3-a] carbazole in the synthesis

Instead of 5- (5-chloro-2-nitrophenyl) -1H-indazole used in <Step 3> of Preparation Example 1 7-chloro-3-phenyl-3,10- obtained in <Step 4> of Preparation Example 1 Except for using dihydropyrazolo [4,3-a] carbazole (14.67 g, 46.17 mmol), 7-chloro-3,10-diphenyl-3, 10-dihydropyrazolo [4,3-a] carbazole (14.72 g, yield 81%) was obtained.

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

<Step 2> of 3,10-diphenyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3,10-dihydropyrazolo [4,3-a] carbazole synthesis

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

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

Step 3 Synthesis of IC-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, and 5- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole instead of 3,10-diphenyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- IC-4 was obtained by the same procedure as <Step 2> of Preparation Example 1, except that yl) -3,10-dihydropyrazolo [4,3-a] carbazole (12.34 g, 25.43 mmol) was used. .

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, 2H), 10.24 (s, 1H)

Preparation Example 5 Synthesis of IC-5

Except for using 5-bromo-1H-indazole (4.17 g, 21.19 mmol) instead of 3-bromo-9H-carbazole used in <Step 3> of Preparation Example 4, and <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 Synthesis of IC-6

Using 7-chloro-3-phenyl-3,10-dihydropyrazolo [4,3-a] carbazole (6.73 g, 21.19 mmol) instead of 3-bromo-9H-carbazole used in <Step 3> of Preparation Example 4 Except for this, IC-6 was obtained by performing 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 Synthesis of IC-7

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

Preparation was carried out 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. 5- (4-chloro-2-nitrophenyl) -1H-indazole (14.61 g, 59% yield) was obtained in the same manner as in <Step 2> of Example 1.

¹ H-NMR: δ 7.63 (d, 1H), 7.99 (m, 3H), 8.18 (s, 1H), 8.39 (m, 2H), 12.39 (s, 1H)

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

5- (4-chloro-2-nitrophenyl) -1H-indazole (12.63 g, 46.17 mmol) was used instead of 5- (5-chloro-2-nitrophenyl) -1H-indazole used in <Step 3> of Preparation Example 1. Except for using, the same procedure as in <Step 3> of Preparation Example 1 was conducted to obtain 5- (4-chloro-2-nitrophenyl) -1-phenyl-1H-indazole (11.78 g, yield 73%). .

¹ H-NMR: δ 7.45 (m, 1H), 7.60 (m, 5H), 7.97 (m, 2H), 8.05 (s, 1H), 8.39 (m, 3H)

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

5- (4-chloro-2-nitrophenyl) -1-phenyl-1H-indazole instead of 5- (5-chloro-2-nitrophenyl) -1-phenyl-1H-indazole used in <Step 4> of Preparation Example 1 Except for using (5.56 g, 15.91 mmol), 8-chloro-3-phenyl-3,10-dihydropyrazolo [4,3-a] carbazole was prepared in the same manner as in <Step 4> of Preparation Example 1. (2.68 g, yield 53%) was obtained.

¹ H-NMR: δ 7.01 (d, 1H), 7.42 (m, 3H), 7.60 (m, 4H), 8.06 (d, 1H), 8.33 (m, 2H), 10.11 (s, 1H)

Step 4 Synthesis of IC-7

8-chloro-3-phenyl-3,10-dihydropyrazolo [4,3] instead of 7-chloro-3-phenyl-3,10-dihydropyrazolo [4,3-a] carbazole used in <Step 5> of Preparation Example 1 IC-7 was obtained by the same procedure as in <Step 5> of Preparation Example 1, except that -a] carbazole (2.68 g, 8.43 mmol) was used.

¹ H-NMR: δ 7.50 (m, 15H), 7.89 (m, 4H), 8.18 (d, 1H), 8.35 (m, 2H), 8.55 (d, 1H), 10.13 (s, 1H)

Synthesis Example 1 Synthesis of C-1

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

After the reaction was completed, 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 was purified by column chromatography to give the title compound C-1 (5.27 g, yield 66%).

GC-Mass (Theoretical value: 600.71 g / mol, Measured value: 600 g / mol)

Synthesis Example 2 Synthesis of C-2

Except for using 2- (4-bromophenyl) triphenylene (10.18 g, 26.57 mmol) instead of bromobenzene used in Synthesis Example 1, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound C-2 (7.80 g, Yield 71%).

GC-Mass (Theoretical value: 826.98 g / mol, Measured value: 826 g / mol)

Synthesis Example 3 Synthesis of C-3

A target compound C was prepared by the same procedure as in Synthesis Example 1, except that 4- (3-bromophenyl) dibenzo [b, d] thiophene (9.01 g, 26.57 mmol) was used instead of bromobenzene in Synthesis Example 1. -3 (7.80 g, yield 75%) was obtained.

GC-Mass (Theoretical value: 782.95 g / mol, Measured value: 782 g / mol)

Synthesis Example 4 Synthesis of C-4

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

GC-Mass (Theoretical value: 854.99 g / mol, Measured value: 854 g / mol)

Synthesis Example 5 Synthesis of C-5

The same procedure as in Synthesis Example 1 was carried out except that 2-bromo-4,6-diphenyl-1,3,5-triazine (8.29 g, 26.57 mmol) was used instead of bromobenzene in Synthesis Example 1. The compound C-5 (5.72 g, Yield 57%) was obtained.

GC-Mass (Theoretical value: 755.87 g / mol, Measured value: 755 g / mol)

Synthesis Example 6 Synthesis of C-6

The same procedure as in Synthesis Example 1 except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (10.31 g, 26.57 mmol) was used instead of bromobenzene in Synthesis Example 1. C-6 (8.84 g, yield 80%) was obtained as a target compound.

GC-Mass (Theoretical value: 831.96 g / mol, Measured value: 831 g / mol)

Synthesis Example 7 Synthesis of C-7

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 instead of bromobenzene. Then, the same procedure as in Synthesis Example 1 was performed to obtain C-7 (7.94 g, yield 82%) as a target compound.

GC-Mass (Theoretical value: 728.84 g / mol, Measured value: 728 g / mol)

Synthesis Example 8 Synthesis of C-8

2- (4'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (instead of 2-bromo-4-phenylquinazoline used in Synthesis Example 7 12.34 g, 26.57 mmol) was obtained in the same manner as in Synthesis Example 7 to obtain C-8 (8.45 g, yield 70%) as a target compound.

GC-Mass (Theoretical value: 908.06 g / mol, Measured value: 908 g / mol)

Synthesis Example 9 Synthesis of C-9

Instead of IC-1 used in Synthesis Example 1, compound IC-3 (6.32 g, 13.29 mmol) synthesized in Preparation Example 3 was used, and 4-bromo-N, N-diphenylaniline (8.61 g, 26.57 mmol) was used instead of bromobenzene. Except for using the same procedure as in Synthesis Example 1, the title compound C-9 (5.25 g, yield 55%) was obtained.

GC-Mass (Theoretical value: 718.85 g / mol, Measured value: 718 g / mol)

Synthesis Example 10 Synthesis of C-10

Except for using 4-([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (8.42 g, 26.57 mmol) instead of 4-bromo-N, N-diphenylaniline used in Synthesis Example 9. , Compound C-10 (8.64 g, yield 86%) was obtained in the same manner as in Synthesis example 9.

GC-Mass (Theoretical value: 755.87 g / mol, Measured value: 755 g / mol)

Synthesis Example 11 Synthesis of C-11

Instead of IC-1 used in Synthesis Example 1, IC-4 (6.97 g, 13.29 mmol) obtained in Preparation Example 4 was used, and 1-bromo-3,5-diphenylbenzene (8.22 g, 26.57 mmol) was used instead of bromobenzene. Except that, the same process as in Synthesis Example 1 was performed to obtain C-11 (7.80 g, yield 78%) as a target compound.

GC-Mass (Theoretical value: 752.90 g / mol, Measured value: 752 g / mol)

Synthesis Example 12 Synthesis of C-12

The same procedure as in Synthesis 11 was carried out 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 C-12 (6.00 g, 59% yield) as the target compound.

GC-Mass (Theoretical value: 765.90 g / mol, Measured value: 765 g / mol)

Synthesis Example 13 Synthesis of C-13

Instead of IC-1 used in Synthesis Example 1, IC-5 (6.32 g, 13.29 mmol) obtained in Preparation Example 5 was used, and 3-bromo-1,1'-biphenyl (6.19 g, 26.57 mmol) was used instead of bromobenzene. Except for, the same procedure as in Synthesis example 1 was carried out to obtain C-13 (5.25 g, yield 63%) as a target compound.

GC-Mass (Theoretical value: 627.73 g / mol, Measured value: 627 g / mol)

Synthesis Example 14 Synthesis of C-14

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] instead of 3-bromo-1,1'-biphenyl used in Synthesis Example 13 Except for using 4-amine (12.66 g, 26.57 mmol), to obtain the target compound C-14 (8.57 g, 74% yield) by the same procedure as in Synthesis Example 13.

GC-Mass (Theoretical value: 871.04 g / mol, Measured value: 871 g / mol)

Synthesis Example 15 Synthesis of C-15

Instead of IC-1 used in Synthesis Example 1, IC-6 (8.52 g, 13.29 mmol) obtained in Preparation Example 6 was used, and 4- (3-bromophenyl) -2,6-diphenylpyrimidine (10.29 g, 26.57 mmol) instead of bromobenzene. Except for using), the same procedure as in Synthesis Example 1 was performed to obtain C-15 (6.17 g, yield 49%) as a target compound.

GC-Mass (Theoretical value: 947.09 g / mol, Measured value: 947 g / mol)

Synthesis Example 16 Synthesis of C-16

Except for using 2-bromonaphthalene (5.50 g, 26.57 mmol) instead of 4- (3-bromophenyl) -2,6-diphenylpyrimidine used in Synthesis Example 15, the same procedure as in Synthesis Example 15 was performed. C-16 (7.03 g, 69% yield) was obtained.

GC-Mass (Theoretical value: 766.89 g / mol, Measured value: 766 g / mol)

Synthesis Example 17 Synthesis of C-17

Instead of IC-1 used in Synthesis Example 1, IC-7 (6.97 g, 13.29 mmol) obtained in Preparation Example 7 was used, and 10-bromo-9,9-dimethyl-9,10-dihydroacridine (7.66 g, Except for using 26.57 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain C-15 (3.79 g, 39% yield) of the title compound.

GC-Mass (Theoretical value: 731.88 g / mol, Measured value: 731 g / mol)

Synthesis Example 18 Synthesis of C-18

Synthesis Example 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 The same procedure as in 17 was carried out to obtain C-18 (3.93 g, 49% yield) of the title compound.

GC-Mass (Theoretical value: 603.67 g / mol, Measured value: 603 g / mol)

Example 1 Fabrication of Green Organic Electroluminescent 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 manufactured as follows.

A glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was ultrasonically cleaned with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.

On the ITO transparent substrate prepared as above, m-MTDATA (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) was laminated in order to manufacture a green organic EL device.

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

[Examples 2 to 18]

Except for using the compounds C-2 to C-18 synthesized in Synthesis Examples 2 to 18 instead of the compound C-1 used as a host material in the formation of the light emitting layer in Example 1, the same as in Example 1 To produce a green organic electroluminescent device.

Comparative Example 1

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C-1 used as a host material of the emission layer in Example 1. The structure of CBP used is as follows.

[Evaluation Example 1]

For the organic electroluminescent devices manufactured in Examples 1 to 18 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

Table 1

	Host material	Drive 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 above, the green organic electroluminescent devices (Examples 1 to 18, respectively) using the compounds represented by Formula 1 according to the present invention (Compounds C-1 to C-18) as phosphorescent host materials of the emission layer The obtained green organic electroluminescent element was found to have superior current efficiency and drive voltage as compared to the green organic electroluminescent element (the organic electroluminescent element of Comparative Example 1) using CBP as a material of the light emitting layer.

The compound according to the present invention can be used as an organic material layer material of the organic electroluminescent device, preferably a hole injection layer material, a hole transport layer material or a light emitting layer material because of excellent heat resistance, hole injection ability, hole transporting ability, light emitting ability and the like.

In addition, the organic electroluminescent device including the compound according to the present invention in the hole injection layer, the hole transport layer, and / or the light emitting layer may greatly improve aspects of light emission performance, driving voltage, lifetime, efficiency, and the like, and thus, full color display. It can be effectively applied to panels.

Claims (9)

1. A compound represented by the following formula (1).

   [Formula 1]

   

   In Chemical Formula 1,

   R ₁ and R _2, R ₂ and R _3, or one of R ₃ and R ₄ forms a condensed ring represented by formula (2),

   R ₁ to R ₅ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C Aryl group of ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , alkylsilyl group of C ₃ to C ₄₀ , 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 it is selected from the group consisting of C ₆ ~ C ₆₀ arylamine group,

   [Formula 2]

   

   In Chemical Formula 2,

   The dotted line means a site where condensation occurs with the compound of Formula 1,

   R ₆ to R ₉ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C Aryl group of ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , alkylsilyl group of C ₃ to C ₄₀ , 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 it is selected from the group consisting of C ₆ ~ C ₆₀ arylamine group, wherein at least one is represented by the following formula (3),

   [Formula 3]

   

   In Chemical 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 ₂ are each independently N or CR ₁₀ ,

   R ₁₀ and R ₂₁ to R ₂₄ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, and nuclear atom 3 to 40 heterocyclo Alkyl group, C ₆ ~ C ₆₀ Aryl group, Nuclear 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl Group, C ₆ ~ C ₆₀ arylsilyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl force It is selected from the group consisting of a pin oxide group and an arylamine group of C ₆ ~ C ₆₀ , or combine with an adjacent group to form a condensed ring,

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

   The arylene group and heteroarylene group of L _1, the aryl group and heteroaryl group of Ar ₁ to Ar ₃ , the alkyl group, cycloalkyl group, heterocycloalkyl group, and aryl group of R ₁ to R ₁₀ and R ₂₁ to R ₂₄ . , Heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyan Furnace group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₂ ~ C ₄₀ alkyl boron group, aryl of C ₆ ~ C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of the group consisting of an aryl amine With at least one selected document is unsubstituted or substituted.
2. The method of claim 1,

   The compound represented by Formula 1 is selected from the group consisting of compounds represented by the following formula 1a to 1f.

   [Formula 1a]

   

   [Formula 1b]

   

   [Formula 1c]

   

   [Formula 1d]

   

   [Formula 1e]

   

   [Formula 1f]

   

   In Chemical Formulas 1a to 1f,

   Ar ₁ , Ar ₂ and R ₁ to R ₉ are as defined in claim 1.
3. The method of claim 1,

   Formula 3 is a compound, characterized in that selected from the group consisting of the structure represented by the formula 3a to 3h.

   [Formula 3a]

   

   [Formula 3b]

   

   [Formula 3c]

   

   [Formula 3d]

   

   [Formula 3e]

   

   [Formula 3f]

   

   [Formula 3g]

   

   [Formula 3h]

   

   In Chemical Formulas 3a to 3h,

   X ₁ , Y ₁ , Y ₂ , R ₂₁ to R ₂₄ are the same as defined in claim 1,

   X ₂ is selected from the group consisting of O, S, Se and NAr ₄ ,

   Y ₃ and Y ₄ are each independently N or CR ₁₂ ,

   R ₁₂ and R ₂₅ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to 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 Form the

   Ar ₄ is a C ₆ ~ C ₁₈ aryl group, or a heteroaryl group having 5 to 18 nuclear atoms,

   The aryl group and heteroaryl group of Ar ₄ , the alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkyl boron group and aryl boron group of R ₁₂ and R ₂₅ . , Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocyclo Alkyl group, C ₆ -C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl Group, C ₆ ~ C ₆₀ arylsilyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl force Substituted or unsubstituted with one or more selected from the group consisting of a pin oxide group and an arylamine group of C ₆ ~ C ₆₀ ,

   m is an integer of 0-4.
4. The method of claim 1,

   At least one of Ar ₁ to Ar ₃ is a compound characterized in that represented by the formula (4).

   [Formula 4]

   

   In Chemical Formula 4,

   L ₂ is a single bond, an arylene group having ₆ to ₁₈ carbon atoms, 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 group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 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 Selected from the group consisting of groups, or combine with adjacent groups to form a condensed ring,

   The arylene group and heteroarylene group of L ₂ and the alkyl group, aryl group, cycloalkyl group, heterocycloalkyl group, heteroaryl group of R ₁₁ , aryloxy group, alkyloxy group, arylamine group, alkylsilyl group and alkyl boron The group, aryl boron group, arylsilyl group, aryl phosphine group and aryl phosphine oxide group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom number 3 Heterocycloalkyl group of 40 to 40, aryl group of C ₆ ~ C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ ~ C ₄₀ , aryloxy group of C ₆ ~ C ₆₀ , C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ alkyl boron group, 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 ring is a substituted or unsubstituted amine groups at least one member selected from the group consisting of.
5. The method of claim 4, wherein

   Formula 4 is a compound, characterized in that selected from the group consisting of the structures represented by A-1 to A-15.

   

   In the above A-1 to A-15,

   L ₂ and R ₁₁ are as defined in claim 4, wherein a plurality of R ₁₁ are the same or different from each other,

   R ₂₆ is hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₁ ~ C ₄₀ groups of the alkyl silyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of a silyl or, by combining groups adjacent to form a fused ring,

   The alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylborone group, arylphosphine group, arylphosphine oxide group and arylsilyl group of R ₂₆ 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 aryl group, 5 to 5 nuclear atoms each independently 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ to C _Is substituted or unsubstituted with one or more selected from the group consisting of ₄₀ aryl phosphine oxide group and C ₆ ~ C ₄₀ arylsilyl group,

   n is an integer of 0-4.
6. The method of claim 4.

   Wherein L ₁ and L ₂ are each independently a single bond, a phenylene group, or a biphenylene group.
7. An organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode.

   At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 6, characterized in that the organic electroluminescent device.
8. The method of claim 7, wherein

   The organic material layer containing the compound is an organic electroluminescent device, characterized in that selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer.
9. The method of claim 7, wherein

   The organic material layer containing the compound is a light emitting layer, the compound is an organic electroluminescent device, characterized in that the phosphorescent host.