WO2019039723A1 - Organic compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising same. The compound according to the present invention is used in an organic layer of an organic electroluminescent device, preferably a light-emitting layer, and can increase the luminous efficiency, driving voltage, and lifespan of the organic electroluminescent device.

Description

Organic compounds and organic electroluminescent devices containing them

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

The electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 were followed up with the observation of organic thin film emission from Bernanose in the 1950s. In 1987, And a functional layer of a light-emitting layer. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.

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. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

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

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescence, the phosphorescent dopant as well as phosphorescent host materials are being studied extensively.

To date, NPB, BCP and Alq ₃ have been widely known as the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.

However, conventional organic material layers are advantageous from the viewpoint of light emitting properties, but their thermal stability is not very good due to their low glass transition temperature, and thus they are not satisfactory in terms of lifetime of the organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.

It is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and which is excellent in hole, electron injection, transporting ability, and light emitting ability.

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

In order to achieve the above object, the present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;

Ar ₁ and R ₁ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Wherein L ₁ and L ₂ of the arylene group and a heteroarylene group, wherein Ar ₁ and Alkyl group of R ₁ to R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they are the same as or different from each other;

Ring A is represented by any one of the following formulas (2) to (5);

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

The dotted line means the part where the condensation is made;

m is an integer from 0 to 4;

n is an integer from 0 to 6;

R ₁₃ is independently 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 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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 An aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ phosphazene-aryl group, is selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the R ₁₃ in this case, these are the same or different, and plural individual;

Alkyl group of the R _13, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ A C ₆ to C ₆₀ arylphosphonyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, And when they are substituted with a plurality of substituents, they are the same as or different from each other.

The present invention provides an organic electroluminescent device including 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 one or more compounds represented by Formula 1 .

"Alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.

As used herein, the term " alkenyl " is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.

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

&Quot; Aryl " in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like. "Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

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

&Quot; Arylamine " in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

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

&Quot; Heterocycloalkyl " in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

&Quot; Alkylsilyl " in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and " arylsilyl " means silyl substituted with aryl having 5 to 60 carbon atoms.

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

Since the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.

1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

One. New organic compounds

The novel compounds of the present invention can be represented by the following formula

[Chemical Formula 1]

In Formula 1,

L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;

Ar ₁ and R ₁ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Wherein L ₁ and L ₂ of the arylene group and a heteroarylene group, wherein Ar ₁ and Alkyl group of R ₁ to R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they are the same as or different from each other;

Ring A is represented by any one of the following formulas (2) to (5);

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

The dotted line means the part where the condensation is made;

m is an integer from 0 to 4;

n is an integer from 0 to 6;

R ₁₃ is independently 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 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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 An aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ phosphazene-aryl group, is selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the R ₁₃ in this case, these are the same or different, and plural individual;

Alkyl group of the R _13, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ A C ₆ to C ₆₀ arylphosphonyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, And when they are substituted with a plurality of substituents, they are the same as or different from each other.

More specifically, the compound represented by formula (1) of the present invention has a basic skeleton of substituted or unsubstituted asymmetric dibenzocarbazole. Since the entire skeleton has a bipolar characteristic due to the binding of a substituted or unsubstituted quinoxaline group, which is one of electron-withdrawing groups (EWG) having a high electron absorbing property, it can increase the binding force between holes and electrons.

The core of the compound represented by formula (I) of the present invention is a structure in which two naphthalene groups having high hole mobility are condensed. Thus, the stability and mobility of holes can be increased higher than those of naphthalene monohydrated skeletons. Further, by introducing a quinoxaline group having a high electron mobility as a substituent, the flow of holes and electrons can be performed well. Accordingly, the number of the excitons contributing to light emission in the light emitting layer can be increased, the light emitting efficiency of the device can be improved, the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased. In addition, the steric hindrance between the core and the electron drag (EDG) is further increased compared to the symmetrical dibenzocarbazole, and the luminous efficiency of the device can be improved.

Therefore, the compound represented by the general formula (1) of the present invention is useful as an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (red phosphorescent host material), an electron transporting layer / injection layer material emitting auxiliary layer material, More preferably, it can be used as a light emitting layer material, an electron transporting layer material, and an electron transporting layer material. In addition, the organic electroluminescent device including the compound of Formula 1 can be greatly improved in performance and lifetime, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize its performance.

According to one preferred embodiment of the present invention, the compound may be represented by any one of the following formulas (6) to (9):

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas (6) to (9)

m, n, L ₁ , L _2, Ar ₁ and R ₁ to R ₁₃ are each as defined in formula (1).

According to a preferred embodiment of the invention, the Ar ₁ and R ₁ to R ₁₂ are each independently selected from hydrogen, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and the nuclear atoms of 5 to 60 heteroaryl group the group consisting of, wherein Ar ₁ and The alkyl group, aryl group and heteroaryl group of R ₁ to R ₁₂ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the invention, the Ar ₁ and R ₁ to R ₁₂ are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxynyl group, and is preferably a group selected from the group consisting of a methyl group,

The Ar < ₁ & A substituted or unsubstituted alkyl group having from ₁ to ₁₂ carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ arylamine group, C ₆ ~ C ₆₀ aryl group and a nuclear atoms substituted with at least one member selected from the group consisting of 5 to 60 heteroaryl group substituent or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different from each other .

According to a preferred embodiment of the invention, the Ar ₁ and R ₁ to R ₁₂ are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxynyl group, and is preferably a group selected from the group consisting of a methyl group,

The Ar < ₁ & A substituted or unsubstituted alkyl group having from ₁ to ₁₂ carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, A phenyl group, a terphenyl group, a naphthalenyl group, a phenanthrenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, An alkenyl group, an alkenyl group, an alkenyl group, an alkenyl group, an alkenyl group, an alkenyl group, an alkenyl group, an alkenyl group, an alkenyl group, an alkynyl group,

According to a preferred embodiment of the invention, the Ar ₁ and At least one of R ₁ to R ₁₂ may be a substituent represented by any one of the following formulas B-1 to B-12:

In the above Formulas B-1 to B-12,

* Denotes the part where the bond is made;

R ₁₄ to R ₁₆ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ phosphazene-aryl group of C _60, the group is bonded to adjacent or selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of forming a condensed ring,

Alkyl group of said R ₁₄ to R _16, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ may be a substituent represented by any one of formulas B-1 to B-7, and at least one of R ₁ to R ₁₂ may be a substituent represented by any one of formulas B-8 to B- -12, more preferably the R ₂ may be a substituent represented by any one of formulas B-8 to B-12.

According to a preferred embodiment of the present invention, in the above Formulas B-10 and B-11, each of R ₁₄ to R ₁₆ is independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A heteroaryl group having 5 to 60 nuclear atoms;

The alkyl group, aryl group and heteroaryl group of R ₁₄ to R ₁₆ 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 ₆ to C ₆₀ An aryl group, and a heteroaryl group having 5 to 60 ring atoms, and when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, each of R ₁₄ to R ₁₆ is independently hydrogen, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, A group consisting of a phenyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, Lt; / RTI >

Examples of the alkyl group of R ₁₄ to R _{16 include} a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group, A thiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ an arylamine group, C ₆ ~ C ₆₀ aryl group and a nuclear atoms substituted with at least one member selected from 5 to 60 heteroaryl group the group consisting of substituted or is unsubstituted, in the case where the substitution of a plurality of substituents, these are equal to each other, or Can be different.

According to a preferred embodiment of the present invention, L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of the following formulas C-1 to C-4, preferably a direct bond or a C- 1 or C-2, more preferably L < _{2 >} is a direct bond or a linker represented by C-1 or C-2:

In the above formulas C-1 to C-4,

* Means the part where the combination is made.

The compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic electroluminescent device

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

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

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI >

The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, referring to FIG. 1, an anode 10 and a cathode 20 facing each other, 20). ≪ / RTI > Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. A hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32. An electron transporting auxiliary layer 35 may be interposed between the electron transporting layer 34 and the light emitting layer 32 can do.

2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).

In the present invention, the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO. The layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.

The electron injecting layer 36 is a layer which is stacked on the electron transporting layer to facilitate injection of electrons from the cathode to ultimately improve the power efficiency. For example, LiF, Liq, NaCl, CsF, Li ₂ O, BaO, or the like can be used.

In addition, although not shown in the drawings, the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32. The light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32. The light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.

In addition, although not shown in the drawings, a life improving layer may be further included between the electron transporting auxiliary layer 35 and the light emitting layer 32. Holes moving in the organic light emitting device due to the ionization potential level in the light emitting layer 32 are blocked by the high energy barrier of the lifetime enhancing layer and do not diffuse or move to the electron transporting layer and consequently function to limit the holes to the light emitting layer . The function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .

In the present invention, the compound represented by the above formula (1) has a substituted or unsubstituted asymmetric dibenzocarbazole as a basic skeleton and a substituted or unsubstituted quinoxaline as an electron attracting group (EWG) Since the whole molecule has a bipolar characteristic due to the bonding of groups, it is possible to enhance the bonding force between holes and electrons.

The core of the compound of the present invention is a structure in which two naphthalene groups having a high hole mobility are condensed. The structure and mobility of holes can be increased higher than those of the naphthalene monohydric skeleton, and quinoxaline By introducing a group as a substituent, holes and electrons can flow well. Accordingly, the number of the excitons contributing to light emission in the light emitting layer can be increased, the light emitting efficiency of the device can be improved, the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased. In addition, the steric hindrance between the core and the electron drag (EDG) is further increased compared to the symmetrical dibenzocarbazole, and the luminous efficiency of the device can be improved.

Accordingly, the compound represented by the formula (1) of the present invention can be used as any one of a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer which are organic compound layers of an organic electroluminescent device. Transporting layer and an electron transporting layer, and more preferably an electron transporting layer, or an electron transporting layer.

When the compound according to the present invention is used as a light emitting layer material, specifically, the compound represented by the above formula (1) can be used as a phosphorescent host, a fluorescent host or a dopant material of a light emitting layer, Preferably a red phosphorescent host material.

In addition, the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.

The organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 To form another 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 usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

The anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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

[Preparation Example 1] Synthesis of Core-1

<Step 1> Synthesis of 2-nitro-1,2'-binaphthalene

2-naphthyl boronic acid (20.0 g, 116.3 mmol) and 1-bromo-2-nitro naphthalene (29.3 g, 116.3 mmol) and _{Pd (PPh 3) 4 (5.4} g, 4.7 mmol), NaOH (14.0 g, 348.9 mmol) were dissolved in 400 ml of tetrahydrofuran and 200 ml of water, and the mixture was stirred at 75 ° C for 4 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 2-nitro-1,2'-binaphthalene (30.0 g, yield 86%) was obtained by column chromatography.

^{1 H-NMR: δ 7.58 (} s, 1H), 7.59 (m, 2H), 7.73 (d, 1H), 7.79 (m, 1H), 7.83 (m, 1H), 7.92 (d, 1H), 8.00 ( (d, IH), 8.22 (d, IH), 8.26 (d, IH), 8.32

<Step 2> Synthesis of Core-1

(30.0 g, 100.2 mmol), triphenylphosphine (65.7 g, 250.5 mmol) and o-dichlorobenzene (100 ml) were mixed and stirred at 190 ° C for 12 hours . After completion of the reaction, o-dichlorobenzene was removed and the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed, and then purified by column chromatography to obtain Core-1 (22.0 g, yield 81%).

^{1 H-NMR: δ 7.57 (} d, 1H), 7.63 (d, 1H), 7.65 (d, 1H), 7.67 (m, 4H), 8.12 (d, 1H), 8.16 (d, 2H), 8.51 ( d, 1 H), 8.54 (d, 1 H), 10.1 (s, 1 H)

[Preparation Example 2] Synthesis of Core-2

<Step 1> Synthesis of Core-2

(15.5 g, 112.2 &lt; RTI ID = 0.0 &gt; mmol) &lt; / RTI &gt; were added to a mixture of Core-1 (10.0 g, 37.4 mmol), 2,3- dichlorobenzo [f] quinoxaline (9.3 g, 37.4 mmol) and N- dimethylaminopyridine mmol) were added to DMF (50 ml), and the mixture was stirred at 75 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, the silica was filtered and then recrystallized with toluene to obtain the target compound Core-2 (12.0 g, yield 67%).

^{1 H-NMR: δ 7.57 (} d, 1H), 7.67 (m, 8H), 7.94 (d, 1H), 7.96 (d, 1H), 8.12 (d, 1H), 8.16 (d, 3H), 8.51 ( d, 2 H), 8.54 (d, 1 H)

[Preparation Example 3] Synthesis of Core-3

<Step 1> Synthesis of 4-chloro-2-nitro-1,2'-binaphthalene

2-naphthyl boronic acid (20.0 g, 116.3 mmol) and 1-bromo-4-chloro-2-nitro naphthalene (33.3 g, 116.3 mmol) and _{Pd (PPh 3) 4 (5.4} g, 4.7 mmol), NaOH (14.0 g, 348.9 mmol) were dissolved in 400 ml of tetrahydrofuran and 200 ml of water, and the mixture was stirred at 75 ° C for 4 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 4-chloro-2-nitro-1,2'-binaphthalene (33.0 g, yield 85%) was obtained by column chromatography.

^{1 H-NMR: δ 7.58 (} s, 1H), 7.59 (m, 2H), 7.73 (d, 1H), 7.90 (m, 1H), 7.92 (d, 1H), 7.99 (m, 1H), 8.00 ( d, 3H), 8.37 (s, IH), 8.88 (d, IH)

Step 2 Synthesis of 5-chloro-7H-dibenzo [a, g] carbazole

(33.0 g, 98.9 mmol), triphenylphosphine (64.8 g, 247.2 mmol) and o-dichlorobenzene (100 ml) were mixed, and the mixture was stirred at 190 占 폚 for 12 hours Lt; / RTI &gt; After completion of the reaction, o-dichlorobenzene was removed and the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which the water had been removed, and the residue was purified by column chromatography to obtain 5-chloro-7H-dibenzo [a, g] carbazole (24.5 g, yield 82%).

¹ H-NMR:? 7.55 (m, 2H), 7.57 (s, IH), 7.57 (d, IH), 7.67 (m, 2H), 8.08 1H), 8.51 (d, 1H), 8.55 (d, 1H), 10.1

<Step 3> Synthesis of Core-3

(10 g, 33.1 mmol), carbazole (5.5 g, 33.1 mmol) and Pd ₂ (dba) ₃ (1.2 g, 1.3 mmol), P (t -Bu) ₃ (0.5 g, 2.6 mmol) and NaO (t-Bu) (8.0 g, 82.8 mmol) were added to 100 ml of toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, 100 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound Core-3 (12.0 g, yield 85%).

^{1 H-NMR: δ 7.25 (} t, 1H), 7.29 (m, 1H), 7.33 (m, 1H), 7.50 (m, 1H), 7.55 (m, 2H), 7.57 (d, 1H), 7.63 ( (d, 1H), 7.67 (m, 2H), 7.83 (s, 1H), 7.94 , &Lt; / RTI &gt; 1H), 8.55 (d, 2H), 10.1

[Preparation Example 4] Synthesis of Core-4

<Step 1> Synthesis of Core-4

-7H- 5-chloro-dibenzo [a, g] carbazole (10.0 g, 33.1 mmol) and dibenzo [b, d] thiophene-3 Daily acid (7.6 g, 33.1 mmol) and Pd (PPh _{3) 4} (1.5 g, 1.3 mmol) and NaOH (4.0 g, 99.3 mmol) were dissolved in 100 ml of tetrahydrofuran and 50 ml of water, and the mixture was stirred at 75 ° C for 4 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, Core-4 (11.5 g, yield 77%) was obtained by column chromatography.

^{1 H-NMR: δ 7.50 (} m, 1H), 7.52 (t, 1H), 7.55 (m, 2H), 7.57 (d, 1H), 7.62 (s, 1H), 7.67 (m, 2H), 7.98 ( 8.15 (d, 1H), 8.05 (d, 1H), 8.08 (s, 1H), 8.11 , &Lt; / RTI &gt; 1H), 8.55 (d, 2H), 10.1

[Synthesis Example 1] Synthesis of Compound 1

2-Chloro-3-phenylquinoxaline (4.5 g, 18.7 mmol), N-dimethylaminopyridine (0.2 g, 1.9 mmol) and potassium carbonate (7.6 g, 56.1 mmol) Was added to 50 ml of DMF and stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 1 (7.1 g, yield 81%) as a target compound.

[LCMS]: 471

[Synthesis Example 2] Synthesis of Compound 2

(5.9 g, 18.7 mmol) and N-dimethylaminopyridine (0.2 g, 18.7 mmol) were added to a solution of Core-1 (5.0 g, 18.7 mmol) , 1.9 mmol) and potassium carbonate (7.6 g, 56.1 mmol) were added to DMF (50 ml), and the mixture was stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 2 (10.2 g, yield 83%) as a target compound

[LCMS]: 547

[Synthesis Example 3] Synthesis of Compound 7

(5.4 g, 18.7 mmol) and N-dimethylaminopyridine (0.2 g, 1.9 mmol) and potassium carbonate (5.7 g, 7.6 g, 56.1 mmol) were added to DMF (50 ml), and the mixture was stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized with toluene to obtain Compound 7 (7.5 g, yield 77%) as a target compound

[LCMS]: 521

[Synthesis Example 4] Synthesis of Compound 8

(5.4 g, 18.7 mmol) and N-dimethylaminopyridine (0.2 g, 1.9 mmol) and potassium carbonate (5.9 g, 7.6 g, 56.1 mmol) were added to DMF (50 ml), and the mixture was stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 8 (6.5 g, yield 67%) as a target compound

[LCMS]: 521

[Synthesis Example 5] Synthesis of Compound 17

(5.4 g, 18.7 mmol) and N-dimethylaminopyridine (0.2 g, 1.9 mmol) and potassium carbonate (7.6 g, , 56.1 mmol) were added to DMF (50 ml), and the mixture was stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 17 (12.0 g, yield 85%) as a target compound

[LCMS]: 521

[Synthesis Example 6] Synthesis of Compound 18

A mixture of Core-1 (5 g, 18.7 mmol), 2 - ([1,1'-biphenyl] -4-yl) -3- chlorobenzo [f] quinoxaline (6.9 g, 18.7 mmol) Pyridine (0.2 g, 1.9 mmol) and potassium carbonate (7.6 g, 56.1 mmol) were added to DMF (50 ml), and the mixture was stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 18 (8.3 g, yield 74%) as a target compound

[LCMS]: 597

[Synthesis Example 7] Synthesis of Compound 20

(6.4 g, 18.7 mmol) and N-dimethylaminopyridine (0.2 g, 1.9 mmol) were added to a solution of Core-1 (5 g, 18.7 mmol) , Potassium carbonate (7.6 g, 56.1 mmol) were added to DMF (50 ml), and the mixture was stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 20 (8.8 g, yield 82%) as a target compound

[LCMS]: 571

[Synthesis Example 8] Synthesis of Compound 23

A Core-2 (5 g, 10.4 mmol) and phenylboronic acid (1.3 g, 10.4 mmol) and _{Pd (PPh 3) 4 (0.5} g, 1.2 mmol), NaOH (1.4 g, 34.7 mmol) in tetrahydrofuran 50 ml And 20 ml of water, and the mixture was stirred at 75 ° C for 12 hours. The solids formed after the reaction was terminated. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 23 (4.4 g, yield 81%).

[LCMS]: 521

[Synthesis Example 9] Synthesis of Compound 25

(2.8 g, 11.6 mmol) and N-dimethylaminopyridine (0.1 g, 1.2 mmol) and potassium carbonate (4.8 g, 34.7 mmol) in DMF Was added to 50 ml of DMF and stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 25 (5.6 g, yield 76%).

 [LCMS]: 636

[Synthesis Example 10] Synthesis of Compound 30

(2.7 g, 11.1 mmol) and N-dimethylaminopyridine (0.1 g, 1.1 mmol) and potassium carbonate (4.6 g, 33.4 mmol) were added to a mixture of Core-4 (5 g, 11.1 mmol) Was added to 50 ml of DMF and stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized with toluene to obtain Compound 30 (5.7 g, yield 79%) as a target compound.

[LCMS]: 653

[Synthesis Example 11] Synthesis of Compound 37

2-chloro-3-phenylbenzo [4,5] thieno [2,3-b] pyrazine (5.5 g, 18.7 mmol) and N-dimethylaminopyridine (0.2 g, , 1.9 mmol) and potassium carbonate (7.6 g, 56.1 mmol) were added to DMF (50 ml), and the mixture was stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 37 (6.6 g, yield 67%) as a target compound.

[LCMS]: 527

[Synthesis Example 12] Synthesis of Compound 44

2,3-b] pyrazine (4.6 g, 18.7 mmol) and 2-chloro-3- (naphthalen-2-yl) benzo [4,5] thieno [ Dimethylaminopyridine (0.2 g, 1.9 mmol) and potassium carbonate (7.6 g, 56.1 mmol) were added to DMF (50 ml) and stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 46 (8.0 g, yield 74%) as a target compound.

[LCMS]: 577

[Synthesis Example 13] Synthesis of Compound 53

3-phenylbenzofuro [2,3-b] pyrazine (5.2 g, 18.7 mmol) and N-dimethylaminopyridine (0.2 g, 1.9 mmol) Potassium carbonate (7.6 g, 56.1 mmol) was added to 50 ml of DMF and stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized with toluene to obtain Compound 53 (7.5 g, yield 78%) as a target compound.

 [LCMS]: 511

[Synthesis Example 14] Synthesis of Compound 65

3-phenylbenzo [4,5] thieno [2,3-b] pyrazine (3.4 g, 11.6 mmol) and N-dimethylaminopyridine (0.1 g, , 1.2 mmol) and potassium carbonate (4.8 g, 34.7 mmol) were added to DMF (50 ml), and the mixture was stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 65 (5.5 g, yield 69%) as a target compound.

 [LCMS]: 692

[Synthesis Example 15] Synthesis of Compound 76

2-chloro-3-phenylbenzofuro [2,3-b] pyrazine (3.3 g, 11.6 mmol) and N-dimethylaminopyridine (0.1 g, 1.2 mmol) Potassium carbonate (4.8 g, 34.7 mmol) was added to 50 ml of DMF and stirred at 120 ° C for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain Compound 76 (5.7 g, yield 73%) as a target compound.

[LCMS]: 676

[Examples 1 to 15] Preparation of red organic EL device

15 compounds synthesized in Synthesis Examples 1 to 15 were subjected to high purity sublimation purification according to a conventionally known method, and red organic EL devices were fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / A-10 to D-15 + 10% Ir (piq) ₂ acac (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

The structures of m-MTDATA, TCTA, Ir (piq) ₂ acac, A, B and BCP are as follows.

[Comparative Example 1] Production of red organic EL device

A red organic EL device was fabricated in the same manner as in Example 1 as a light emitting host material in the formation of a light emitting layer.

[Evaluation example]

Current efficiency and emission peak at a current density (10) mA / cm 2 were measured for each of the red organic EL devices manufactured in Examples 1 to 15 and Comparative Examples 1 and 2. The results are shown in the following Table 1 Respectively.

Sample	Host	The driving voltage (V)	EL peak (nm)	Current efficiency (cd / A)
Example 1	One	4.5	620	45.1
Example 2	2	4.3	620	46,2
Example 3	7	4.5	620	44.1
Example 4	8	4.5	620	44.3
Example 5	17	4.6	620	45.1
Example 6	18	4.7	620	45,2
Example 7	20	4.5	620	44.3
Example 8	23	4.6	620	44.1
Example 9	25	4.5	620	46.1
Example 10	30	4.6	620	47.1
Example 11	37	4.6	620	49.8
Example 12	44	4.7	620	44.3
Example 13	53	4.7	620	43.2
Example 14	65	4.6	620	41.2
Example 15	76	4.6	620	41.2
Comparative Example 1	A	5.3	620	35.2
Comparative Example 2	B	5.2	620	37.1

As shown in Table 1, when the compound (1 to 86) according to the present invention was used as a light emitting layer of a red organic EL device (Example 1-15), a red organic EL device (Comparative Example 1 , 2), it can be seen that it shows better performance in terms of efficiency and driving voltage.

[Description of Symbols]

10: anode 20: cathode

30: organic layer 31: hole transport layer

32: light emitting layer 33: hole transporting auxiliary layer

34: Electron transport layer 35: Electron transport layer

36: electron injection layer 37: hole injection layer

Claims (11)

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

   [Chemical Formula 1]

   

   In Formula 1,

   L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;

   Ar ₁ and R ₁ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

   Wherein L ₁ and L ₂ of the arylene group and a heteroarylene group, wherein Ar ₁ and Alkyl group of R ₁ to R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they are the same as or different from each other;

   Ring A is represented by any one of the following formulas (2) to (5);

   (2)

   

   (3)

   

   [Chemical Formula 4]

   

   [Chemical Formula 5]

   

   In the above formulas 2 to 5,

   The dotted line means the part where the condensation is made;

   m is an integer from 0 to 4;

   n is an integer from 0 to 6;

   R ₁₃ is independently 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 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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 An aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ phosphazene-aryl group, is selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the R ₁₃ in this case, these are the same or different, and plural individual;

   Alkyl group of the R _13, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ A C ₆ to C ₆₀ arylphosphonyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, And when they are substituted with a plurality of substituents, they are the same as or different from each other.
2. The method according to claim 1,

   Wherein said compound is represented by any one of the following formulas (6) to (9):

   [Chemical Formula 6]

   

   (7)

   

   [Chemical Formula 8]

   

   [Chemical Formula 9]

   

   In the above formulas (6) to (9)

   m, n, L ₁ , L _2, Ar ₁ and R ₁ to R ₁₃ are each as defined in claim 1.
3. The method according to claim 1,

   The Ar &lt; ₁ & Each of R ₁ to R ₁₂ is independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,

   The Ar &lt; ₁ & The alkyl group, aryl group and heteroaryl group of R ₁ to R ₁₂ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms And when they are substituted with a plurality of substituents, they are the same as or different from each other.
4. The method according to claim 1,

   The Ar &lt; ₁ & Wherein at least one of R ₁ to R ₁₂ is a substituent represented by any one of the following formulas B-1 to B-12:

   

   In the above Formulas B-1 to B-12,

   * Denotes the part where the bond is made;

   R ₁₄ to R ₁₆ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ phosphazene-aryl group of C _60, the group is bonded to adjacent or selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of forming a condensed ring,

   Alkyl group of said R ₁₄ to R _16, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl And when they are substituted with a plurality of substituents, they are the same as or different from each other.
5. 5. The method of claim 4,

   Wherein Ar ₁ is a compound wherein the substituent represented by any one of the general formula B-1 to B-7.
6. 5. The method of claim 4,

   At least one of R ₁ to R ₁₂ is a substituent represented by any one of formulas (B-8) to (B-12).
7. 5. The method of claim 4,

   Wherein R &lt; ₂ &gt; is a substituent represented by any one of formulas (B-8) to (B-12).
8. The method according to claim 1,

   Wherein L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of the following formulas C-1 to C-4:

   
9. The method according to claim 1,

   Wherein said compound is selected from the group consisting of:

   

   

   

   

   

   

   

   
10. 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,

    Wherein at least one of the one or more organic layers includes a compound represented by the general formula (1).
11. 11. The method of claim 10,

    Wherein the organic material layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transporting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and a light emitting layer.

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