KR102441870B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same, wherein the compound according to the present invention is used in an organic material layer, preferably a light emitting layer, of the organic electroluminescent device, so that the luminous efficiency, driving voltage, and lifespan of the organic electroluminescent device etc. can be improved.

Description

Organic compound and organic electroluminescent device comprising the same

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

Starting with the observation of organic thin film emission by Bernanose in the 1950s, research on organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 continued. ) presented an organic electroluminescent device having a stacked structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of a specialized material used for this.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, an exciton is formed, and when the exciton falls to the ground state, light is emitted. In this case, 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, etc. according to their function.

The light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing a better natural color according to the emission color. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a 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. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, research on phosphorescent host materials as well as the phosphorescent dopant is in progress.

Until now, NPB, BCP, Alq ₃ and the like have been widely known as materials for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as materials for the light emitting layer. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) ₂ , which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

However, conventional organic material layer materials are advantageous in terms of light emitting properties, but have not been satisfactory in terms of the lifespan of the organic electroluminescent device because the glass transition temperature is low and thermal stability is not very good. Accordingly, there is a demand for the development of an organic layer material having excellent performance.

The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent hole, electron injection and transport ability, light emitting ability, and the like.

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

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

[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 ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ and R ₁ To R ₁₂ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group;

The arylene group and the heteroarylene group of L ₁ and L ₂ , the Ar ₁ and R ₁ To R ₁₂ Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ With one or more substituents selected from the group consisting of an arylsilyl group When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other;

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

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,

The dotted line indicates the portion where the condensation takes place;

m is an integer from 0 to 4;

n is an integer from 0 to 6;

R ₁₃ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ an arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when R ₁₃ is a plurality, they are the same or different from each other;

An _alkyl group, 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 alkylboron group, an arylboron group, The arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ of aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ substituted with one or more substituents selected from the group consisting of arylsilyl group, or When unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other.

The present invention provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer comprises the compound of 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, and hexyl. and the like, but is not limited thereto.

"Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds, and examples thereof include vinyl, Allyl (allyl), isopropenyl (isopropenyl), there are 2-butenyl (2-butenyl) and the like, but is not limited thereto.

"Alkynyl" in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond, an example of which is ethynyl) , 2-propynyl, and the like, but is not limited thereto.

“Aryl” in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, in which a single ring or two or more rings are combined. In addition, two or more rings are condensed with each other, contain only carbon as a ring-forming atom (eg, the number of carbon atoms may be 8 to 60), and the whole molecule is monovalent having non-aromaticity. 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. In this case, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply attached to or condensed with each other, and contain a hetero atom selected from N, O, P, S and Se in addition to carbon as a ring forming atom, and the entire molecule is non-aromatic (non-aromatic). It is interpreted to include a monovalent group having aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

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

"Alkyloxy" in the present invention is a monovalent substituent represented by R'O-, wherein R' means 1 to 40 alkyl, and has a linear, branched or cyclic structure. interpreted as including Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

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

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

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 5 to 60 carbon atoms.

"Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

Since the compound of the present invention has excellent thermal stability, carrier transport ability, light emitting ability, and the like, it can be usefully 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 has greatly improved aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel.

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 compound of the present invention may be represented by the following formula (1):

[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 ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ and R ₁ To R ₁₂ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group;

The arylene group and the heteroarylene group of L ₁ and L ₂ , the Ar ₁ and R ₁ To R ₁₂ Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ With one or more substituents selected from the group consisting of an arylsilyl group When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other;

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

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,

The dotted line indicates the portion where the condensation takes place;

m is an integer from 0 to 4;

n is an integer from 0 to 6;

R ₁₃ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ an arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when R ₁₃ is a plurality, they are the same or different from each other;

An _alkyl group, 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 alkylboron group, an arylboron group, The arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ of aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ substituted with one or more substituents selected from the group consisting of arylsilyl group, or When unsubstituted and 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 substituted or unsubstituted asymmetric dibenzo carbazole as a basic skeleton. Since the substituted or unsubstituted quinoxaline group, which is one of the electron withdrawing groups (EWG) having high electron absorbing property, is bonded to the basic skeleton, the entire molecule has a bipolar characteristic, thereby increasing the bonding force between holes and electrons.

The core of the compound represented by Formula 1 of the present invention has a structure in which two naphthalene groups having high hole mobility are condensed, and thus, stability and mobility for higher holes can be increased compared to a skeleton made of one naphthalene. In addition, by introducing a quinoxaline group having high electron mobility as a substituent, holes and electrons can flow well. Accordingly, the number of excitons contributing to light emission in the light emitting layer may be increased to improve the luminous efficiency of the device, and the durability and stability of the device may be improved to effectively increase the lifetime of the device. In addition, the steric hindrance between the core and electron withdrawing (EDG) is further increased compared to the symmetric dibenzo carbazole, so that the luminous efficiency of the device can be improved.

Therefore, the compound represented by Formula 1 of the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (a red phosphorescent host material), an electron transport layer/injection layer material, a light emission auxiliary layer material, an electron transport auxiliary layer material, More preferably, it may be used as a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material. In addition, the performance and lifespan characteristics of the organic electroluminescent device including the compound of Formula 1 can be greatly improved, and the performance of a full color organic light emitting panel to which such an organic electroluminescent device is applied can also be maximized.

According to a preferred embodiment of the present invention, the compound may be represented by any one of the following Chemical Formulas 6 to 9:

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 6 to 9,

Each of m, n, L ₁ , L _{2 ,} Ar ₁ and R ₁ to R ₁₃ is as defined in Formula 1.

According to a preferred embodiment of the present invention, the Ar ₁ and R ₁ to R ₁₂ are each 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, 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. When substituted or unsubstituted with the above substituents and 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, the Ar ₁ and R ₁ to R ₁₂ are each 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 phenanthrenyl group, a triphenylenyl group, a pyridinyl group, a pyridinyl group It is selected from the group consisting of a midinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxynyl group,

Ar ₁ and R ₁ To R ₁₂ Methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group, pyrimidinyl group, triazinyl group A group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxynyl group are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ arylamine Group, C ₆ ~ C ₆₀ When substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and substituted with a plurality of substituents, they may be the same or different from each other can

According to a preferred embodiment of the present invention, the Ar ₁ and R ₁ to R ₁₂ are each 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 phenanthrenyl group, a triphenylenyl group, a pyridinyl group, a pyridinyl group It is selected from the group consisting of a midinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxynyl group,

Ar ₁ and R ₁ To R ₁₂ Methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group, pyrimidinyl group, triazinyl group A group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxynyl group are each independently a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a bi Phenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorenyl group, spiroflu When unsubstituted or substituted with one or more substituents selected from the group consisting of an orenyl group and a dibenzodioxynyl group, and 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, the Ar ₁ and At least one of R ₁ to R ₁₂ may be a substituent represented by any one of the following Chemical Formulas B-1 to B-12:

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

* means the part where the bond is formed;

R ₁₄ to R ₁₆ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group, and C ₆ ~ C ₆₀ A condensed ring is formed by combining or adjacent groups selected from the group consisting of an arylamine group,

An alkyl group, 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 alkylboron group, an aryl group of R ₁₄ to R ₁₆ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of an arylsilyl group When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, the 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, and more Preferably, 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 Formulas B-10 and B-11, R ₁₄ to R ₁₆ are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and selected from the group consisting of 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 ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ When unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, the R ₁₄ to R ₁₆ are each 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, phenanthree The group consisting of a nyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxynyl group is selected from

and 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 phenanthrenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidinyl group, A triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxynyl group are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ An arylamine group, a C ₆ ~ C ₆₀ aryl group, and one or more substituents selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms, or unsubstituted, and substituted with a plurality of substituents, they are the same as each other or may 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 C- It may be a linker represented by 1 or C-2, more preferably L ₂ may be a direct bond or a linker represented by C-1 or C-2:

In Formulas C-1 to C-4,

* means the part where the bond is made.

The compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

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

2. abandonment electric field light emitting element

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by Formula 1 according to the present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is and a compound represented by Formula 1 above. In this case, the compounds may be used alone or in mixture of two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic material layer of the above formula It may include a compound represented by 1.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them. Here, the organic layer 30 may include a hole transport layer 31 , a light emitting layer 32 , and an electron transport layer 34 . In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the emission layer 32 , and an electron transport auxiliary layer 35 is included between the electron transport layer 34 and the emission layer 32 . can do.

Referring to FIG. 2 as another example of the present invention, 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 An electron injection layer 36 may be further included between (20).

In the present invention, the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 improves the interface characteristics between ITO used as the anode and the organic material used as the hole transport layer 31 as well. Rather, it is a layer that is applied on top of ITO whose surface is not flat and has a function of making the surface of ITO soft. However, the present invention is not limited thereto.

In addition, the electron injection layer 36 is laminated on top of the electron transport layer to facilitate electron injection from the cathode and ultimately to improve power efficiency. It can be used without limitation, for example, LiF, Liq, NaCl, CsF, Li ₂ O, a material such as BaO can be used.

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

In addition, although not shown in the drawings in the present invention, a life improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32 . Holes moving at an ionization potential level in the organic light emitting layer to the light emitting layer 32 are blocked by the high energy barrier of the life improvement layer and cannot diffuse or move to the electron transport layer, resulting in limiting the holes to the light emitting layer. . This function of limiting holes to the light emitting layer prevents the diffusion of holes into the electron transport layer that moves electrons by reduction, thereby suppressing the lifespan decrease through the irreversible decomposition reaction caused by oxidation, thereby contributing to the improvement of the lifespan of the organic light emitting device. can

In the present invention, the compound represented by Formula 1 has a substituted or unsubstituted asymmetric dibenzo carbazole as a basic skeleton, and a substituted or unsubstituted quinoxaline that is one of electron withdrawing groups (EWG) with high electron absorption in the basic skeleton Since the groups are bonded and the entire molecule has a bipolar characteristic, it is possible to increase the bonding force between holes and electrons.

The core of the compound of the present invention has a structure in which two naphthalene groups with high hole mobility are condensed, and stability and mobility for higher holes can be increased compared to a skeleton made of one naphthalene, and quinoxaline with high electron mobility By introducing the group as a substituent, the flow of holes and electrons can be achieved well. Accordingly, the number of excitons contributing to light emission in the light emitting layer may be increased to improve the luminous efficiency of the device, and the durability and stability of the device may be improved to effectively increase the lifetime of the device. In addition, the steric hindrance between the core and electron withdrawing (EDG) is further increased compared to the symmetric dibenzo carbazole, so that the luminous efficiency of the device can be improved.

Therefore, the compound represented by Formula 1 of the present invention may be used as any one material of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer which is an organic material layer of an organic electroluminescent device, but preferably a light emitting layer, an electron It may be used as a material of any one of the transport layer and the electron transport auxiliary layer that is further laminated on the electron transport layer, more preferably, the electron transport layer or the electron transport auxiliary layer.

In addition, when the compound according to the present invention is used as a light emitting layer material, specifically, the compound represented by Formula 1 may be used as a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, preferably as a phosphorescent host material, more Preferably, it can be used as a red phosphorescent host material.

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

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (eg, an electron transport auxiliary layer) is formed to include the compound represented by Formula 1 above. It can be manufactured by forming another organic material layer and an electrode using it.

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

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets may be used.

In addition, the anode material may be made of, for example, a conductor having a high work function to facilitate hole injection, and may include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and 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 is not limited thereto.

In addition, as the negative electrode material, for example, it may be made of a low work function conductor to facilitate electron injection, and may be formed of magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. the same metal or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

Hereinafter, the present invention will be described in detail through examples. However, the following examples only illustrate the present invention, and the present invention is not limited by the following examples.

[ preparation example 1] Core - 1 of synthesis

<Step 1> 2-nitro-1,2'- Binaphthalene synthesis of

2-naphthyl boronic acid (20.0 g, 116.3 mmol) with 1-bromo-2-nitronaphthalene (29.3 g, 116.3 mmol) and Pd(PPh ₃ ) ₄ (5.4 g, 4.7 mmol), NaOH (14.0 g, 348.9 mmol) was added with 400 ml of tetrahydrofuran and 200 ml of water and stirred at 75° C. for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 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, 2H), 8.22 (d, 1H), 8.26 (d, 1H), 8.32 (d, 1H), 8.81 (d, 1H)

<Step 2> Core- 1 of synthesis

2-Nitro-1,2'-binaphthalene (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, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water was removed, it was 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, 1H), 8.54 (d, 1H), 10.1 (s, 1H)

[ preparation example 2] Core - 2 of synthesis

<Step 1> Core- 2 of synthesis

Core-1 (10.0 g, 37.4 mmol) with 2,3-dichlorobenzo [f] quinoxaline (9.3 g, 37.4 mmol) and N-dimethylaminopyridine (0.5 g, 3.7 mmol), potassium carbonate (15.5 g, 112.2) mmol) was added to 50 ml of DMF and stirred at 75° C. for 12 hours. After completion of the reaction, 50 ml of water was added and stirred. The resulting solid was stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from 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, 2H), 8.54 (d, 1H)

[ preparation example 3] Core - 3 of synthesis

<Step 1> 4- Chloro -2-nitro-1,2'- Binaphthalene synthesis of

2-naphthyl boronic acid (20.0 g, 116.3 mmol) with 1-bromo-4-chloro-2-nitronaphthalene (33.3 g, 116.3 mmol) and Pd(PPh ₃ ) ₄ (5.4 g, 4.7 mmol), NaOH (14.0 g, 348.9 mmol) was added with 400 ml of tetrahydrofuran and 200 ml of water and stirred at 75° C. for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 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, 1H), 8.88 (d, 1H)

<Step 2> 5- Chloro -7H- Dibenzo[a,g]carbazole synthesis of

Chloro-2-nitro-1,2'-binaphthalene (33.0 g, 98.9 mmol), triphenylphosphine (64.8 g, 247.2 mmol) and o-dichlorobenzene (100 ml) were mixed and 190 ° C. for 12 hours stirred. After completion of the reaction, o-dichlorobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water was removed, it was purified by column chromatography to obtain 5-chloro-7H-dibenzo[a,g]carbazole (24.5 g, yield 82%).

¹ H-NMR: δ 7.55 (m, 2H), 7.57 (s, 1H), 7.57 (d, 1H), 7.67 (m, 2H), 8.08 (d, 1H), 8.12 (d, 1H), 8.16 ( d, 1H), 8.51 (d, 1H), 8.55 (d, 1H), 10.1 (s, 1H)

<Step 3> Core- 3 of synthesis

5-chloro-7H-dibenzo[a,g]carbazole (10.0 g, 33.1 mmol) with 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 toluene and stirred at 110° C. for 12 hours. After completion of the reaction, 100 ml of water was added and stirred. The resulting solid was stirred. After the filter, the solid was dissolved in toluene and recrystallized from toluene after silica filter 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 (d, 1H), 8.08 (d, 1H), 8.12 (d, 3H), 8.16 (d, 1H), 8.51 (d) , 1H), 8.55 (d, 2H), 10.1 (s, 1H)

[ preparation example 4] Core - 4 of synthesis

<Step 1> Core- 4 of synthesis

5-chloro-7H-dibenzo[a,g]carbazole (10.0 g, 33.1 mmol) with dibenzo[b,d]thiophen-3-ylboronic acid (7.6 g, 33.1 mmol) and Pd(PPh ₃ ) ₄ (1.5 g, 1.3 mmol), NaOH (4.0 g, 99.3 mmol), 100 ml of tetrahydrofuran and 50 ml of water were added, and the mixture was stirred at 75° C. for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 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 ( d, 1H), 8.05 (d, 1H), 8.08 (s, 1H), 8.11 (d, 1H), 8.12 (d, 1H), 8.16 (d, 1H), 8.45 (d, 1H), 8.51 (d) , 1H), 8.55 (d, 2H), 10.1 (s, 1H)

[ Synthesis example 1] Compound 1 of synthesis

Core-1 (5.0 g, 18.7 mmol) with 2-chloro-3-phenylquinoxaline (4.5 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 1 (7.1 g, yield 81%).

[LCMS]: 471

[ Synthesis example 2] Compound 2 of synthesis

Core-1 (5.0 g, 18.7 mmol) with 2-([1,1'-biphenyl]-4-yl)-3-chloroquinoxaline (5.9 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 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 2 (10.2 g, yield 83%).

[LCMS]: 547

[ Synthesis example 3] Compound 7 of synthesis

Core-1 (5 g, 18.7 mmol) with 2-chloro-3-(naphthalen-1-yl)quinoxaline (5.4 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 7 (7.5 g, yield 77%).

[LCMS]: 521

[ Synthesis example 4] Compound 8 of synthesis

Core-1 (5 g, 18.7 mmol) with 2-chloro-3- (naphthalen-2-yl) quinoxaline (5.4 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 stirred. After the filter, the solid was dissolved in toluene and recrystallized from toluene after silica filter to obtain the target compound, Compound 8 (6.5 g, yield 67%).

[LCMS]: 521

[ Synthesis example 5] Compound 17 of synthesis

Core-1 (5 g, 18.7 mmol) with 3-chloro-2-phenylbenzo [f] quinoxaline (5.4 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 17 (12.0 g, yield 85%).

[LCMS]: 521

[ Synthesis example 6] Compound 18 of synthesis

Core-1 (5 g, 18.7 mmol) and 2-([1,1'-biphenyl]-4-yl)-3-chlorobenzo[f]quinoxaline (6.9 g, 18.7 mmol) and N-dimethylamino Pyridine (0.2 g, 1.9 mmol) and potassium carbonate (7.6 g, 56.1 mmol) were 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 18 (8.3 g, yield 74%).

[LCMS]: 597

[ Synthesis example 7] Compound 20 of synthesis

Core-1 (5 g, 18.7 mmol) with 3-chloro-2-(naphthalen-2-yl)benzo[f]quinoxaline (6.4 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 stirred. After the filter, the solid was dissolved in toluene and recrystallized from toluene after silica filter to obtain the target compound, Compound 20 (8.8 g, yield 82%).

[LCMS]: 571

[ Synthesis example 8] Compound 23 of synthesis

Core-2 (5 g, 10.4 mmol) with phenyl boronic 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 50 ml of tetrahydrofuran and 20 ml of water and stirred at 75° C. for 12 hours. After completion of the reaction, the resulting solid was stirred. After the filter, the solid was dissolved in toluene and recrystallized from toluene after silica filter to obtain the target compound, Compound 23 (4.4 g, yield 81%).

[LCMS]: 521

[ Synthesis example 9] Compound 25 of synthesis

Core-3 (5 g, 11.6 mmol) with 2-chloro-3-phenylquinoxaline (2.8 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 stirred. After the filter, the solid was dissolved in toluene and recrystallized from toluene after silica filter to obtain the target compound, Compound 25 (5.6 g, yield 76%).

[LCMS]: 636

[ Synthesis example 10] Compound 30 of synthesis

Core-4 (5 g, 11.1 mmol) with 2-chloro-3-phenylquinoxaline (2.7 g, 11.1 mmol) and N-dimethylaminopyridine (0.1 g, 1.1 mmol), potassium carbonate (4.6 g, 33.4 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 30 (5.7 g, yield 79%).

[LCMS]: 653

[ Synthesis example 11] Compound 37 of synthesis

Core-1 (5 g, 18.7 mmol) with 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 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 37 (6.6 g, yield 67%).

[LCMS]: 527

[ Synthesis example 12] Compound 44 of synthesis

Core-1 (5 g, 18.7 mmol) and 2-chloro-3- (naphthalen-2-yl) benzo [4,5] thieno [2,3-b] pyrazine (4.6 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 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 46 (8.0 g, yield 74%).

[LCMS]: 577

[ Synthesis example 13] Compound 53 of synthesis

Core-1 (5 g, 18.7 mmol) with 2-chloro-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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 53 (7.5 g, yield 78%).

[LCMS]: 511

[ Synthesis example 14] Compound 65 of synthesis

Core-3 (5 g, 11.6 mmol) with 2-chloro-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 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 stirred. After the filter, the solid was dissolved in toluene, filtered through silica, and recrystallized from toluene to obtain the target compound, Compound 65 (5.5 g, yield 69%).

[LCMS]: 692

[ Synthesis example 15] Compound 76 of synthesis

Core-3 (5 g, 11.6 mmol) with 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 stirred. After the filter, the solid was dissolved in toluene and recrystallized from toluene after silica filter to obtain the target compound, Compound 76 (5.7 g, yield 73%).

[LCMS]: 676

[ Example 1 ~ 15] Fabrication of red organic EL device

After high-purity sublimation purification of 15 kinds of compounds synthesized in Synthesis Examples 1 to 15 according to a commonly known method, a red organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). The substrate was transferred to

m-MTDATA (60 nm)/TCTA (80 nm)/ each compound of A-10 to D-15 + 10 % Ir(piq) ₂ acac (30 nm)/BCP (10 nm)/ An organic EL device was fabricated by stacking Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) in the order.

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

[ comparative example 1] Fabrication of red organic EL device

A red organic EL device was manufactured in the same manner as in Example 1 as a light emitting host material when the light emitting layer was formed.

[ evaluation example ]

For each of the red organic EL devices manufactured in Examples 1 to 15 and Comparative Examples 1 and 2, 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 shown in

Sample host drive 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 compounds (1 to 86) according to the present invention were used as a light emitting layer of a red organic EL device (Example 1-15), a red organic EL device using a conventional similar structural compound (Comparative Example 1) , 2) shows better performance in terms of efficiency and driving voltage.

10: positive electrode 20: negative electrode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transport auxiliary layer
34: electron transport layer 35: electron transport auxiliary layer
36: electron injection layer 37: hole injection layer

Claims (11)

A compound represented by the following formula (1):
[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 ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;
Ar ₁ and R ₁ To R ₁₂ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group;
The arylene group and heteroarylene group of L ₁ and L ₂ , the Ar ₁ and R ₁ To R ₁₂ Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ With one or more substituents selected from the group consisting of an arylsilyl group When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other;
Ring A is represented by any one of the following formulas 3 to 5;
[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 3 to 5,
The dotted line indicates the portion where the condensation takes place;
m is an integer from 0 to 4;
n is an integer from 0 to 6;
R ₁₃ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ an arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when R ₁₃ is a plurality, they are the same or different from each other;
An _alkyl group, 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 alkylboron group, an arylboron group, The arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ of aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ substituted with one or more substituents selected from the group consisting of arylsilyl group, or When unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other. According to claim 1,
The compound is a compound represented by any one of Formulas 7 to 9:
[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 7 to 9,
Each of m, n, L ₁ , L _{2 ,} Ar ₁ and R ₁ to R ₁₃ is as defined in claim 1 . According to claim 1,
Ar ₁ and R ₁ to R ₁₂ are each 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,
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. When substituted with or unsubstituted with more than one substituent, and substituted with a plurality of substituents, they are the same or different from each other. According to claim 1,
Ar ₁ and A compound in which 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,
* means the part where the bond is formed;
R ₁₄ to R ₁₆ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group, and C ₆ ~ C ₆₀ A condensed ring is formed by combining or adjacent groups selected from the group consisting of an arylamine group,
An alkyl group, 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 alkylboron group, an aryl group of R ₁₄ to R ₁₆ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of an arylsilyl group When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other. 5. The method of claim 4,
Ar ₁ is a substituent represented by any one of Formulas B-1 to B-7. 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. 5. The method of claim 4,
wherein R ₂ is a substituent represented by any one of Formulas B-8 to B-12. According to claim 1,
The 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, a compound:

According to claim 1,
The compound is a compound characterized in that it is selected from the group consisting of:

An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device comprising a compound represented by the formula (1) of claim 1. 11. The method of claim 10,
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 transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer, an organic electroluminescent device.

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