KR20190076376A - 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. A compound according to the present invention is used for an organic layer, preferably a light emitting layer of the organic electroluminescent device, thereby being able to improve luminous efficiency, driving voltage, lifespan and the like of the organic electroluminescent device.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound 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 make 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,

m is an integer from 0 to 4;

n and l are each independently an integer of 0 to 3;

Y ₁ and Y ₂ is a single bond, O, S, Se, N (R ₄₎ and _{C (R 5) (R 6} ) a is selected from the group consisting, with the proviso that Y ₁ and Y ₂ is a single bond at the same time, each independently Not;

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

X ₁ to X ₄ are each independently N or C (R ₇ ), and one of them is necessarily N;

Any one of X ₁ to X ₄ bonded to L ₂ is C (R ₇ ), wherein R ₇ is a member;

Z ₁ to Z ₃ are each independently N or C (R ₈ ), and one is necessarily N;

Ar ₁ and Ar ₂ 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 ~ C ₆₀ aryl phosphazene group, selected from the group consisting of a C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and an aryl amine of the C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring,

R ₁ to R ₈ 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 ~ aryl phosphazene group of C _60, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C selected from the ₆₀ group consisting of aryl amines, or to combine groups which are adjacent to form a fused ring, wherein R ₁ to R ₈ are plural, they are the same as or different from each other;

The arylene group and the heteroarylene group of L ₁ and L ₂ and the Ar ₁ and Ar ₂ And R ₁ to the alkyl group of R _8, 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.

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,

m is an integer from 0 to 4;

n and l are each independently an integer of 0 to 3;

Y ₁ and Y ₂ is a single bond, O, S, Se, N (R ₄₎ and _{C (R 5) (R 6} ) a is selected from the group consisting, with the proviso that Y ₁ and Y ₂ is a single bond at the same time, each independently Not;

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

X ₁ to X ₄ are each independently N or C (R ₇ ), and one of them is necessarily N;

Any one of X ₁ to X ₄ bonded to L ₂ is C (R ₇ ), wherein R ₇ is a member;

Z ₁ to Z ₃ are each independently N or C (R ₈ ), and one is necessarily N;

Ar ₁ and Ar ₂ 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 ~ C ₆₀ aryl phosphazene group, selected from the group consisting of a C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and an aryl amine of the C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring,

R ₁ to R ₈ 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 ~ aryl phosphazene group of C _60, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C selected from the ₆₀ group consisting of aryl amines, or to combine groups which are adjacent to form a fused ring, wherein R ₁ to R ₈ are plural, they are the same as or different from each other;

The arylene group and the heteroarylene group of L ₁ and L ₂ and the Ar ₁ and Ar ₂ And R ₁ to the alkyl group of R _8, 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.

More specifically, the compound represented by the formula (1) of the present invention is a compound having a nitrogen-containing heterocycle (e.g., a pyridine group, a pyrimidine group, a triazine group, etc.) in the basic skeleton of benzopyrrolopyridine (BFP) (EDG) such as an electron donor (EWG) having a high electron absorbing property and an electron donating group (EWG) such as nitrogen, oxygen, a sulfur containing heterocycle (e.g., carbazole, phenoxazine, dibenzofuran, fluorene, etc.) Is bipolar, has strong electrochemical stability, has excellent electron transportability, and has high triplet energy, glass transition temperature, and thermal stability.

The compounds of the present invention are capable of controlling the electron withdrawing ability by a novel form of benzopyropyridine and can fine tuning the LUMO state of the molecule, It is easy to adjust the band gap, steric hindrance, and film state property. This improves the mobility of electrons and can be applied as an effective N-type material or a bipolar material. In particular, fine tuning of Hall characteristics and electronic properties can be achieved by introducing EDG, aryl, or heteroaryl group into the pyridine group, EWG or aryl, heteroaryl group, and benzofuran group by applying BFP having a benzofuran group and a pyridine group, And can be used as a material of any one of a light emitting layer, an electron transporting layer, an electron transporting auxiliary layer and an electron transporting layer which are organic materials layers of an organic electroluminescent device.

Therefore, the compound represented by the general formula (1) of the present invention can be used as an organic layer material of an organic electroluminescence device, preferably a light emitting layer material (green 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 2 to 7:

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 2 to 7,

m, n, l, L ₁ , L _2, R ₁ to R ₆ , X ₁ to X ₄ , Z ₁ to Z _3, Ar ₁ and Ar ₂ are each as defined in formula (1).

According to a preferred embodiment of the present invention, the compound may be represented by any one of the following formulas (8) to (10), preferably represented by the following formula (9)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the above formulas (8) to (10)

m, n, l, Y ₁ , Y _2, L ₁ , L _2, R ₁ to R _3, Z ₁ to Z _3, Ar ₁ and Ar ₂ are each as defined in formula (1).

According to a preferred embodiment of the present invention, each of R ₁ to R ₆ is 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 _Wherein the alkyl, aryl and heteroaryl groups of R ₁ to R ₆ 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.

According to a preferred embodiment of the present invention, each of R ₁ to R ₆ independently represents 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 selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,

Examples of the substituent groups of R ₁ to R _{6 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 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 aryl substituted with an amine group, C ₆ ~ C ₆₀ aryl group and a nuclear atoms 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, they are same or different, Do.

According to a preferred embodiment of the present invention, each of R ₁ to R ₆ independently represents 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 selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,

Examples of the substituent groups of R ₁ to R _{6 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 dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, Examples of the aryl group include 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 and a dibenzodioxynyl group, 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, L ₁ and L ₂ are each independently a single bond or a linker selected from the group consisting of the following formulas A-1 to A-4, preferably a single bond, May be a linker represented by the following formula A-1 or A-2, more preferably L < _{2 >} may be a single bond or a linker represented by A-1 or A-

In the above Formulas A-1 to A-4,

* Means the part where the combination is made.

According to a preferred embodiment of the present invention, the linker represented by A-1 may be a linker represented by the following formula (B-1) or (B-2)

In the above formula (B-1) or (B-2)

* Means the part where the combination is made.

According to a preferred embodiment of the present invention, Ar ₁ and Ar ₂ 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 the alkyl, aryl and heteroaryl groups of Ar ₁ and Ar ₂ 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.

According to a preferred embodiment of the present invention, Ar ₁ and Ar ₂ each independently represent a hydrogen atom, 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 selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,

Examples of the groups represented by Ar ₁ and Ar ₂ include methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl, 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 aryl substituted with an amine group, C ₆ ~ C ₆₀ aryl group and a nuclear atoms 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, they are same or different, Do.

According to a preferred embodiment of the present invention, Ar ₁ and Ar ₂ each independently represent a hydrogen atom, 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 selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,

Examples of the groups represented by Ar ₁ and Ar ₂ include 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 methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, Examples of the aryl group include 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 and a dibenzodioxynyl group, 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 and Ar ₂ may each independently be a substituent represented by any of the following formulas C-1 to C-5:

In the above formulas C-1 to C-5,

* Denotes the part where the bond is made;

p is an integer from 0 to 5;

q is an integer from 0 to 4;

R ₉ 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 ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ aryl phosphazene group of C _60, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent form a condensed ring, and wherein R ₉ and R < ₁₀ > each are the same or different from each other;

Alkyl group of the R ₉ 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 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 Substituted with one or more substituents being unsubstituted or, if substituted by a plurality of substituents, they are same as or different from each other.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ 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 the alkyl, aryl and heteroaryl groups of R ₉ and R ₁₀ 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.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, , A group selected from the group consisting of triphenylenyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spirofluorenyl and dibenzodioxinyl groups Selected,

Examples of the R ₉ and R ₁₀ groups are methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl, triphenylenyl, pyridinyl, 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 aryl substituted with an amine group, C ₆ ~ C ₆₀ aryl group and a nuclear atoms 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, they are same or different, Do.

According to a preferred embodiment of the present invention, the substituent represented by the formula (C-1) may be a substituent represented by any one of the following formulas (D-1) to (D-5).

In the above formulas D-1 to D-5,

* Means the part where the bond 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. abandonment Field  Light emitting element

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, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer. ≪ / RTI > compounds.

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.

Further, although not shown in the drawings in the present invention, an electron transporting auxiliary layer may be further included between the electron transporting layer and the light emitting layer. Holes migrating to the ionization potential level in the organic light emitting element by the light emitting layer 32 are blocked by the high energy barrier of the electron transporting layer and can not diffuse or move to the electron transporting layer and consequently have the function of limiting the holes to the light emitting layer do. 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 .

The compound represented by the general formula (1) of the present invention has an electron-absorbing property such as a nitrogen-containing heterocycle (e.g., pyridine group, pyrimidine group, triazine group, etc.) in the basic skeleton of benzopyrrolopyridine (BFP) Electron donor (EDG) is coupled with this large electron donor (EWG) and nitrogen, oxygen, sulfur containing heterocycle (eg, carbazole, phenoxazine, dibenzofuran, fluorene, etc.) ), Has strong electrochemical stability due to strong bonding, has excellent electron transportability, and has high triplet energy, glass transition temperature, and thermal stability.

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 green 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 S-1

At room temperature, 2,3,5-trichloropyridine (20 g, 109 mmol) and 2-methoxyphenylboronic acid (21.5 g, 141.7 mmol) are placed in a 2-neck flask. Of _{Pd (PPh 3) 4 (5.04g} , 5.67mmol) and potassium fluoride (potassium fluoride) (15.8g, 272.5 mmol) is added. 300 ml of toluene was added, followed by stirring at 100 ° C for 5 hours. After completion of the reaction, the solution is subjected to silica filtration. After removing the solvent, the oil was purified by column chromatography (MC: Hexane = 1: 1) to obtain an oil type transparent compound S-1 (32.6 g, yield 90%).

^{1 H-NMR: δ 3.71 (} s, 3H), 7.03 (t, 1H), 7.12 (d, 1H), 7.20 (d, 1H), 7.44 (t, 1H), 8.23 (s, 1H), 8.61 ( s, 1 H)

 [LCMS]: 253

[ Preparation Example  2] Synthesis of S-2

S-1 (22 g, 86.6 mmol) is dissolved in MC (200 ml) at room temperature. 2-neck flask and slowly add NBS (20 g, 113 mmol). After stirring for 8 hours, add Acetone (100 ml). After completion of the reaction, filter the silica with MC. After removal of the solvent, the residue is purified by column chromatography (MC: Hexane = 1: 1). A pale yellow compound S-2 of oil type (27 g, yield 94%) was obtained.

¹ H-NMR:? 3.74 (s, 3H), 6.85 (d, IH), 7.31 (d, IH), 7.95

 [LCMS]: 332

[ Preparation Example  3] Synthesis of S-3

S-1 (28 g, 84.1 mmol) is dissolved in MC (300 ml) at room temperature and placed in a 2-neck flask. Keep the condition at 0 ℃ in an ice bath. Add BBr ₃ (12.2 ml, 126 mmol) slowly. After completion of the reaction, slowly add H ₂ O (300 ml) at 0 ° C. The reaction is extracted with MC and silica filtered. After removal of the solvent, a pale yellow compound S-3 of oil type (20.4 g, yield 76%) was obtained.

^{1 H-NMR: δ 6.75 (} d, 1H), 7.29 (d, 1H), 7.95 (s, 1H), 7.99 (s, 1H), 8.84 (s, 1H) 9.80 (s, 1H)

 [LCMS]: 318

[ Preparation Example  4] Synthesis of S-4

Add S-3 (16 g, 50 mmol) and KOH (11.2 g, 199 mmol) Na ₂ (S ₂ O ₄ ) (1.6 g, 5 mmol) in a 2-neck flask at room temperature. After adding DMF (200 ml), add tetrabutylammonium bromide (Bu ₄ NBr) (1.74 g, 10 mmol). The mixture was stirred at 130 ° C for 3 hours. After completion of the reaction, H ₂ O (200 ml) is slowly added. The reaction is extracted with MC and silica filtered. After removal of the solvent, white powder compound S-4 (9.6 g, yield 68%) was obtained.

¹ H-NMR:? 7.30-7.36 (m, 2H), 7.65 (s,

 [LCMS]: 282

[ Preparation Example  5] Synthesis of S-5

The procedure of Preparation Example 1 was repeated, except that 2,3,4-trichloropyridine was used as the reactant, to obtain the desired compound S-5 (40 g, yield 79%).

[ Preparation Example  6] Synthesis of S-6

The same procedure as in [Preparation Example 2] was carried out, except that 3,4-dichloro-2- (2-methoxyphenyl) pyridine was used as a reactant to obtain the desired compound S-6 (38.8 g, yield 92% .

^{1 H-NMR: δ 3.80 (} s, 1H), 6.89 (d, 1H), 7.15 ~ 7.22 (m, 2H), 7.34 (t, 1H), 8.66 (d, 1H) 8.83 (d, 1H)

 [LCMS]: 253

[ Preparation Example  7] Synthesis of S-7

The procedure of Preparation Example 3 was repeated except that 2- (5-bromo-2-methoxyphenyl) -3,4-dichloropyridine was used as the reactant, to thereby yield the desired compound S-7 (32 g, yield 65 %).

^{1 H-NMR: δ 6.78 (} d, 1H), 7.20 ~ 7.28 (m, 2H), 7.92 (s, 1H), 8.66 (d, 1H) 8.66 (d, 1H), 9.84 (s, 1H)

[LCMS]: 318

[ Preparation Example  8] Synthesis of S-8

The procedure of Preparation Example 4 was repeated except that 4-bromo-2- (3,4-dichloropyridin-2-yl) phenol was used as a reactant to obtain the target compound S-8 (16.1 g, yield 85 %).

¹ H-NMR:? 7.31-7.45 (m, 3H), 7.69 (s,

[LCMS]: 282

[ Preparation Example  9] Synthesis of S-9

At room temperature, 2,3,5-trichloropyridine (20 g, 109 mmol) and 3-bromo-2-methoxyphenylboronic acid (50.3 g, 218 mmol) are placed in a 2-neck flask. Of _{Pd (PPh 3) 4 (3.78g} , 3.27mmol) and potassium fluoride (potassium fluoride) (8.7g, 218 mmol) is added. 400 ml of toluene was added, followed by stirring at 100 ° C for 5 hours. After completion of the reaction, the solution is subjected to silica filtration. After removal of the solvent, the residue is purified by column chromatography (MC: Hexane = 1: 4) and then purified by column chromatography (EA: Hexane = 1: 4). After removal of the solvent, an oil type compound S-9 (12.34 g, yield 34%) was obtained.

^{1 H-NMR: δ 3.71 (} s, 1H), 6.88 (t, 3H), 7.35 (d, 1H), 8.78 (d, 1H), 8.86 (s, 1H)

[LCMS]: 333

 [ Preparation Example  10] Synthesis of S-10

The procedure of Preparation Example 3 was repeated except that 2- (3-bromo-2-methoxyphenyl) -3,5-dichloropyridine was used as the reactant to obtain the desired compound S-10 (10.9 g, yield 70%).

^{1 H-NMR: δ 6.82 (} t, 1H), 7.29 (d, 3H), 7.94 (s, 1H), 8.72 (d, 1H), 8.85 (s, 1H), 9.84 (s, 1H)

[LCMS]: 318

[ Preparation Example  11] Synthesis of S-11

The procedure of Preparation Example 4 was repeated except that 2-bromo-6- (3,5-dichloropyridin-2-yl) phenol was used as the reactant to obtain the desired compound S-11 (17.3 g, yield 80 %).

¹ H-NMR:? 7.12 (t, 3H), 7.37 (d, IH), 7.65

[LCMS]: 282

[ Preparation Example  12] Synthesis of S-12

The procedure of Preparation Example 8 was repeated, except that 3-bromo-2-methoxyphenylboronic acid and 2,3,4-trichloropyridine were used as the reactants, to obtain the target compound S-12 (11.3 g, Yield: 29%).

^{1 H-NMR: δ 3.73 (} s, 1H), 6.81 (t, 1H) 7.29 (d, 1H), 7.40 (d, 1H), 8.66 (d, 1H), 8.78 (d, 1H)

[LCMS]: 333

[ Preparation Example  13] Synthesis of S-13

The procedure of Preparation Example 3 was repeated except that 2- (3-bromo-2-methoxyphenyl) -3,4-dichloropyridine was used as the reactant, to obtain 31.3 g of the desired compound S-13 75%).

^{1 H-NMR: δ 6.82 (} t, 1H), 7.20 ~ 7.28 (m, 2H), 8.61 (d, 1H), 8.75 (d, 1H), 9.83 (s, 1H)

[LCMS]: 318

[ Preparation Example  14] Synthesis of S-14

The procedure of Preparation Example 3 was repeated except that 2-bromo-6- (3,4-dichloropyridin-2-yl) phenol was used as the reactant to obtain the desired compound S-14 (31.3 g, yield 75 %).

¹ H-NMR:? 7.09 (t, 1 H), 7.36-7.45 (m, 2H), 7.70

[LCMS]: 282

[ Preparation Example  15] Synthesis of S-15

S-4 (2.8 g, 9.94 mmol) and 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Carbazole (3.14 g, 11 mmol) in a 2-neck flask. Of _{Pd (PPh 3) 4 (0.34g} , 0.3 mmol) and _{K 2 CO 3 (4.12g, 30} mmol) is added. After adding 100 ml of toluene, the mixture is refluxed for 6 hours. After completion of the reaction, the solution is subjected to silica hot filtration. After removing the solvent, rinse with ethanol. The compound S-15 (1.81 g, yield 41%) was obtained after purification by column chromatography (MC: Hexane = 1: 3).

^{1 H-NMR: δ 7.11 (} t, 1H), 7.20 ~ 7.34 (m, 4H), 7.40 ~ 7.56 (m, 7H), 7.70 (s, 1H), 7.77 (s, 1H), 7.98 (s, 1H ), 8.20 (d, 1 H), 8.79 (s, 1 H)

[LCMS]: 444

[ Preparation Example  16] Synthesis of S-16

Pd (dppf) Cl ₂ (0.53 g 0.72 mmol), KOAc (3.53 g, 36 mmol), bis (pinacolate) diborane (5.5 g, 22 mmol), X -phos (1.72 g, 3.6 mmo) into a 2-neck flask. Add 1.4-dioxane (200 ml) under nitrogen and reflux. After completion of the reaction for 12 hours, the solution is filtered through silica with EA. After removal of the solvent, white powder S-16 (8.8 g, yield 92%) was obtained.

^{1 H-NMR: δ 1.29 (} s, 12H), 7.09 (t, 1H), 7.20 ~ 7.36 (m, 4H), 7.40 ~ 7.56 (m, 7H), 7.71 ~ 7.82 (t, 3H), 8.19 (d , ≪ / RTI > 1H), 8.75 (s, 1H)

[LCMS]: 536

[ Preparation Example  17] Synthesis of S-17

The same procedure as in [Preparation Example 14] was repeated except that 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Respectively. After purification by column chromatography (EA: Hexane = 1: 4), the solvent is removed. The target compound S-17 (6.5 g, yield: 56%) was obtained by recrystallization from toluene.

Yield: 92%).

¹ H-NMR:? 7.35-7.55 (m, 7H), 7.65 (s, IH), 7.72 (s, IH), 7.96

[LCMS]: 369

[ Preparation Example  18] Synthesis of S-18

The procedure of Preparation Example 15 was repeated, except that S-17 was used as the reactant, to obtain the target compound S-18 (3.3 g, yield 77%).

^{1 H-NMR: δ 1.30 (} s, 12H), 7.31 ~ 7.42 (m, 3H), 7.36 ~ 7.56 (m, 3H), 7.64 (s, 1H), 7.71 (s, 1H), 7.80 (s, 1H ), 7.99 (d, 1 H), 8.70 (s, 1 H)

[LCMS]: 461

[ Preparation Example  19] Synthesis of S-19

Except that 10-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) 14]. After purification by column chromatography (EA: Hexane = 1: 4), the solvent is removed. The objective compound S-19 (4.1 g, yield 38%) was obtained by recrystallization from chlorobenzene.

¹ H-NMR:? 6.42-6.51 (m, 4H), 6.58-6.73 (m, 3H), 6.88 (s, 1H), 6.97-7.02 , 7.50 (d, IH), 7.72 (s, IH), 7.98

[LCMS]: 460

[ Preparation Example  20] Synthesis of S-20

The procedure of Preparation Example 15 was followed except that S-19 was used as the reactant to obtain the desired compound S-20 (4.6 g, yield 91%).

¹ H-NMR:? 1.26 (s, 12H), 6.42-6.48 (m, 4H), 6.56-6.74 (m, 3H), 6.89 1H), 7.40 (d, 1H), 7.48 (s, 1H), 7.72

[LCMS]: 552

[ Preparation Example  21] Synthesis of S-21

Except that 2- (9,9-dimethyl-9H-fluoren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used as a reactant. Preparation Example 14] was carried out. Purify with column chromatography (MC: Hexane = 1: 2) and remove the solvent. The target compound S-21 (7.4 g, yield 68%) was obtained by recrystallization from toluene.

^{1 H-NMR: δ 1.76 (} s, 6H), 7.29 (t, 1H), 7.38 ~ 7.60 (m, 5H), 7.70 (s, 1H), 7.77 (s, 1H), 7.84 (d, 1H), 7.90 (d, 1 H), 7.99 (s, 1 H), 8.80 (s, 1 H)

[LCMS]: 395

[ Preparation Example  22] Synthesis of S-22

The procedure of Preparation Example 15 was repeated except that S-21 was used as the reactant, to obtain the desired compound S-22 (6.6 g, yield 80%).

^{1 H-NMR: δ 1.28 (} s, 12), 1.67 (s, 6H), 7.30 (t, 1H), 7.38 ~ 7.41 (m, 2H), 7.48 ~ 7.61 (m, 3H), 7.77 (d, 2H ), 7.80 (s, IH), 7.84 (d, IH), 7.93

[LCMS]: 487

[ Preparation Example  23] Synthesis of S-23

Except that S-8 and 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H- Was carried out in the same manner as in [Preparation Example 14]. After purification by column chromatography (MC: Hexane = 1: 1), the solvent is removed. The target compound S-23 (5.4 g, yield 70%) was obtained by recrystallization from toluene.

^{1 H-NMR: δ 7.18 (} t, 1H), 7.20 ~ 7.38 (m, 4H), 7.40 ~ 7.55 (m, 8H), 7.74 (s, 1H), 7.80 (s, 1H), 8.24 (d, 1H ), 8.66 (d, 1 H)

[LCMS]: 444

[ Preparation Example  24] Synthesis of S-24

The procedure of Preparation Example 15 was followed except that S-23 was used as the reactant to obtain the desired compound S-24 (4.8 g, yield 81%).

The target compound S-23 (5.4 g, yield 70%) was obtained by recrystallization.

^{1 H-NMR: δ 1.32 (} s, 12H), 7.09 (t, 1H), 7.21 ~ 7.36 (m, 4H), 7.40 ~ 7.58 (m, 8H), 7.70 (s, 1H), 7.78 (s, 1H ), 8.31 (d, 1 H), 8.70 (d, 1 H)

[LCMS]: 536

[ Preparation Example  25] Synthesis of S-25

Except that S-11 and 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H- Was carried out in the same manner as in [Preparation Example 14]. After purification by column chromatography (MC: Hexane = 1: 1), the solvent is removed. The resulting solid was washed with ethanol and then recrystallized with toluene to obtain the desired compound S-25 (2.3 g, yield 40%).

^{1 H-NMR: 7.11 (t} , 1H), 7.19 ~ 7.35 (m, 5H), 7.39 ~ 7.54 (m, 5H), 7.70 (d, 1H), 7.81 (s, 1H), 7.97 (d, 1H) , 8.03 (s, IH), 8.27 (d, IH), 8.83 (s, IH)

[LCMS]: 444

[ Preparation Example  26] Synthesis of S-26

The procedure of Preparation Example 15 was repeated except that S-25 was used as a reactant, to obtain the desired compound S-26 (2.0 g, yield 84%).

^{1 H-NMR: 1.34 (s} , 12H), 7.12 (t, 1h), 7.19 ~ 7.32 (m, 5H), 7.39 ~ 7.61 (m, 5H), 7.67 (d, 1H), 7.69 (d, 1H) , 7.78 (d, IH), 7.98 (d, IH), 8.22

[LCMS]: 536

[ Preparation Example  27] Synthesis of S-27

Except that S-14 and 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H- Was carried out in the same manner as in [Preparation Example 14]. After purification by column chromatography (MC: Hexane = 1: 1), the solvent is removed. The obtained solid was washed with methanol and then recrystallized with toluene to obtain the target compound S-27 (5.3 g, yield 60%).

^{1 H-NMR: 7.10 (t} , 1h), 7.22 ~ 7.37 (m, 5H), 7.45 ~ 7.60 (m, 6H), 7.76 (d, 1H), 7.87 (s, 1H), 8.02 (d, 1H) , 8.29 (d, 1 H), 8.64 (d, 1 H)

[LCMS]: 444

[ Preparation Example  28] Synthesis of S-28

The procedure of Preparation Example 15 was followed except that S-27 was used as a reactant to obtain the desired compound S-28 (4.1 g, yield 74%).

[LCMS]: 536

[ Synthetic example  1] Synthesis of Compound A-1

S-16 (5.5 g, 10.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (3.27 g, 12.2 mmol) are placed in a 2-neck flask at room temperature. Of _{Pd (PPh 3) 4 (0.47g} , 0.41 mmol) and NaOH (1.22g, 31 mmol) is added. After adding 200 ml of toluene, the mixture is refluxed for 8 hours. After completion of the reaction, filter the silica by using Toluene. After removing solvent, rinse with distilled water and ethanol. And recrystallized from dichlorobenzene to obtain Compound A-1 (1.81 g, yield 41%).

¹ H-NMR: 7.11 (t, 1 H), 7.20-7.33 (m, 4H), 7.40-7.62 (m, 13H), 7.74 , 8.22 (d, IH), 8.41 (m, 4H), 8.86 (s, IH)

[LCMS]: 641

[ Synthetic example  2] Synthesis of Compound A-9

Same as [Synthesis Example 1] except that S-16 and 2-chloro-4-phenyl-6- (3- (pyridin-3-yl) phenyl) . After purification by column chromatography (EA: Hexane = 1: 1), the solvent is removed. The obtained solid was washed with distilled water and Acetone, and then recrystallized from dichlorobenzene to obtain objective compound A-9 (2.3 g, yield: 58%).

[LCMS]: 718

[ Synthetic example  3] Synthesis of Compound A-13

The same procedure as in [Synthesis Example 1] was carried out except that S-16 and 2-chloro-4-phenyl-6- (dibenzofuran-4-yl) -1,3,5-triazine were used as reactants Respectively. After purification by column chromatography (EA: Hexane = 1: 4), the solvent is removed. The obtained solid was washed with distilled water and Acetone, and then recrystallized from dichloro benzene to obtain objective compound A-13 (4.8 g, yield 72%).

[LCMS]: 731

[ Synthetic example  4] Synthesis of Compound A-1-1

The same procedure as in [Synthesis Example 1] was carried out except that S-22 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used as reactants. Purify with column chromatography (MC: Hexane = 1: 2) and remove the solvent. The obtained solid was washed with distilled water and Acetone, and then recrystallized with toluene to obtain objective compound A-1-1 (2.8 g, yield 66%).

^{1 H-NMR: 7.11 (t} , 1H), 7.28 ~ 7.52 (m, 11H), 7.73 (s, 1H), 7.76 (s, 1H), 7.85 (d, 1H), 7.91 (d, 1H), 8.99 (s, 1 H), 8.39 (m, 4 H), 8.84 (s, 1 H)

[LCMS]: 592

[ Synthetic example  5] Synthesis of Compound A-2-1

The same procedure as in [Synthesis Example 1] was carried out except that S-18 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used as reactants. After purification by column chromatography (EA: Hexane = 1: 2), the solvent is removed. The resulting solid was washed with distilled water and Acetone, and then recrystallized with toluene to obtain objective compound A-1-1 (2.8 g, yield 86%).

^{1 H-NMR: 7.11 (t} , 1H), 7.32 ~ 7.60 (m, 12H), 7.69 (d, 2H), 7.98 (m, 2H), 8.44 (m, 4H), 8.90 (s, 1H)

[LCMS]: 566

[ Synthetic example  6] Synthesis of Compound A-3-1

The same procedure as in [Synthesis Example 1] was carried out except that S-24 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used as reactants. After purification by column chromatography (EA: Hexane = 1: 2), the solvent is removed. The obtained solid was washed with distilled water, methanol and acetone, and then recrystallized from dichlorobenzene to obtain objective compound A-3-1 (1.8 g, yield 72%).

¹ H-NMR: 7.18 (t, 1 H), 7.29-7.33 (m, 4H), 7.40-7.62 (m, 14H) , 8.75 (d, 1 H)

[LCMS]: 641

[ Synthetic example  7] Synthesis of Compound A-3-14

The same procedure as in [Synthesis Example 1] was carried out except that S-24 and 2-chloro-4-phenyl-6- (dibenzofuran-3-yl) -1,3,5-triazine were used as reactants Respectively. After purification by column chromatography (EA: Hexane = 1: 1), the solvent is removed. The obtained solid was washed with distilled water, methanol and acetone, and then recrystallized from dichloro benzene to obtain objective compound A-3-14 (4.4 g, yield 70%).

[LCMS]: 731

[ Synthetic example  8] Synthesis of Compound B-13

Except that S-16 and 2-chloro-4- (dibenzofuran-1-yl) -6- (4- (pyridin-3-yl) phenyl) -1,3,5-triazine were used as reactants Was carried out in the same manner as in [Synthesis Example 1]. After purification by column chromatography (EA: Hexane = 1: 1), the solvent is removed. The obtained solid was washed with distilled water, methanol and acetone, and recrystallized from dichloro benzene to obtain the target compound B-13 (1.3 g, yield 59%).

[LCMS]: 808

[ Synthetic example  9] Synthesis of Compound B-21

The reaction was carried out in the same manner as in Example 1 except that S-16 and 2-chloro-4- (9,9-dimethyl-9H-fluoren-1-yl) -6- (4- (pyridin- The same procedure as in [Synthesis Example 1] was carried out except that triazine was used. Purify with column chromatography (MC: Hexane = 2: 1) and remove the solvent. The obtained solid was washed with distilled water, methanol and acetone, and then recrystallized from dichlorobenzene to obtain the target compound B-21 (1.7 g, yield 69%).

[LCMS]: 834

[ Synthetic example  10] Synthesis of Compound B-3-1

Except that S-26 and 2- (biphenyl-3-yl) -4-chloro-6- (dibenzofuran-1-yl) -1,3,5-triazine were used as reactants 1]. Purify with column chromatography (MC: Hexane = 2: 1) and remove the solvent. The obtained solid was washed with distilled water, methanol and Acetone, and then recrystallized from dichloro benzene to obtain objective compound B-3-1 (0.9 g, yield 44%).

[LCMS]: 807

[ Synthetic example  11] Synthesis of compound B-3-13

Except that S-26 and 2-chloro-4- (dibenzofuran-1-yl) -6- (4- (pyridin-3-yl) phenyl) -1,3,5- Was carried out in the same manner as in [Synthesis Example 1]. After purification by column chromatography (EA: Hexane = 1: 2), the solvent is removed. The obtained solid was washed with distilled water, methanol and acetone, and then recrystallized from chlorobenzene to obtain the target compound B-3-13 (1.2 g, yield 51%).

[LCMS]: 808

[ Synthetic example  12] Synthesis of Compound C-1

The same procedure as in [Synthesis Example 1] was carried out except that S-16 and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine were used as reactants. After purification by column chromatography (MC: Hexane = 1: 3), the solvent is removed. The obtained solid was washed with distilled water, methanol, and acetone, and then recrystallized with toluene to obtain the desired compound C-1 (2.9 g, yield 71%).

^{1 H-NMR: 7.11 (t} , 1H), 7.32 ~ 7.60 (m, 12H), 7.69 (d, 2H), 7.98 (m, 2H), 8.44 (m, 4H), 8.90 (s, 1H)

[LCMS]: 717

[ Synthetic example  13] Synthesis of Compound C-3-1

The same procedure as in [Synthesis Example 1] was carried out except that S-20 and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine were used as reactants. After purification by column chromatography (EA: Hexane = 1: 4), the solvent is removed. The obtained solid was washed with distilled water, methanol and acetone, and recrystallized from chlorobenzene to obtain the target compound C-3-1 (3.1 g, yield 79%).

[LCMS]: 733

[ Synthetic example  14] Synthesis of Compound E-1

The same procedure as in [Synthesis Example 1] was carried out except that S-16 and 4-chloro-2,6-diphenylpyrimidine were used as reactants. After purification by column chromatography (EA: Hexane = 1: 6), the solvent is removed. The obtained solid was washed with distilled water, methanol and acetone, and then recrystallized from chlorobenzene to obtain objective compound E-1 (3.1 g, yield 82%).

^{1 H-NMR: 7.18 (t} , 1H), 7.26 ~ 7.44 (m, 4H), 7.51 ~ 7.61 (m, 13H), 7.85 (d, 2H), 7.95 (d, 2H), 8.07 (s, 1H) , 8.29 (d, IH), 8.35 (s, IH), 8.42 (m, 2H), 8.88

[LCMS]: 640

[ Synthetic example  15] Synthesis of Compound E-2

The same procedure as in [Synthesis Example 1] was carried out except that S-16 and 2- (biphenyl-4-yl) -4-chloro-6-phenylpyrimidine were used as reactants. After purification by column chromatography (EA: Hexane = 1: 5), the solvent is removed. The obtained solid was washed with distilled water, methanol and Acetone, and recrystallized from chlorobenzene to obtain objective compound E-2 (3.6 g, yield 78%).

 [LCMS]: 716

[ Synthetic example  16] Synthesis of Compound E-6

The same procedure as in [Synthesis Example 1] was carried out except that S-16 and 4-chloro-6-phenyl-2- (4- (pyridin-3-yl) phenyl) pyrimidine were used as a reactant. After purification by column chromatography (EA: Hexane = 1: 4), the solvent is removed. The obtained solid was washed with distilled water, methanol and Acetone, and recrystallized from chlorobenzene to obtain the desired compound E-6 (2.9 g, yield 68%).

[LCMS]: 717

[ Synthetic example  17] Synthesis of Compound E-2-1

The same procedure as in [Synthesis Example 1] was carried out except that S-18 and 4-chloro-2,6-diphenylpyrimidine were used as reactants. After purification by column chromatography (EA: Hexane = 1: 4), the solvent is removed. The obtained solid was washed with distilled water, methanol and Acetone, and then recrystallized from dichlorobenzene to obtain objective compound E-2-1 (2.1 g, yield 61%).

^{1 H-NMR: 7.34 ~ 7.55} (m, 13H), 7.74 (s, 1H), 7.87 (s, 1H), 7.88 (d, 2H), 8.02 (d, 2H), 8.32 (s, 1H), 8.39 (m, 2 H), 8.82 (s, 1 H)

[LCMS]: 565

[ Synthetic example  18] Synthesis of compound E-2-6

The same procedure as in [Synthesis Example 1] was carried out except that S-18 and 4-chloro-6-phenyl-2- (4- (pyridin-3-yl) phenyl) pyrimidine were used as a reactant. After purification by column chromatography (MC: Hexane = 1: 3), the solvent is removed. The obtained solid was washed with distilled water, methanol and Acetone, and then recrystallized with toluene to obtain objective compound E-2-6 (3.0 g, yield 67%).

[LCMS]: 642

[ Synthetic example  19] Synthesis of Compound E-3-1

The same procedure as in [Synthesis Example 1] was carried out except that S-28 and 4-chloro-2,6-diphenylpyrimidine were used as reactants. After purification by column chromatography (EA: Hexane = 1: 4), the solvent is removed. The obtained solid was washed with distilled water, methanol and Acetone, and then recrystallized from chlorobenzene to obtain objective compound E-3-1 (3.4 g, yield 70%).

¹ H-NMR: 7.16 (t, 1 H), 7.29-7.40 (m, 5H), 7.50-7.76 (m, 13H), 7.86 , 8.39 (s, 1 H), 8.46 (m, 2 H), 8.75 (d, 1 H)

[LCMS]: 640

[ Synthetic example  20] Synthesis of Compound E-3-2

The same procedure as in [Synthesis Example 1] was carried out except that S-28 and 2- (biphenyl-4-yl) -4-chloro-6-phenylpyrimidine were used as reactants. After purification by column chromatography (EA: Hexane = 1: 5), the solvent is removed. The obtained solid was washed with distilled water, methanol and Acetone, and then recrystallized from chlorobenzene to obtain objective compound E-3-1 (1.4 g, yield 55%).

[LCMS]: 716

[ Synthetic example  21] Synthesis of Compound E-3-3

The same procedure as in [Synthesis Example 1] was carried out except that S-26 and 4-chloro-2,6-diphenylpyrimidine were used as reactants. Purify with column chromatography (MC: Hexane = 1: 2) and remove the solvent. The resulting solid was washed with distilled water, methanol, and acetone, and then recrystallized from chlorobenzene to obtain objective compound E-3-3 (2.0 g, yield 49%).

^{1 H-NMR: 7.14 ~ 7.36} (m, 6H), 7.46 ~ 7.61 (m, 11H), 7.72 (d, 1H), 7.83 (s, 1H), 7.91 (m, 3H), 8.03 (s, 1H) , 8.25 (d, IH), 8.43 (s, IH), 8.48 (m, 2H), 8.97

[LCMS]: 640

[ Example  1 to 21] green organic Field  Fabrication of light emitting device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was 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.

Thus prepared ITO transparent electrode on the m-MTDATA (60 nm) / TCTA (80 nm) / 90% compound 10% in Table _{1 Ir (ppy) 3 (300nm} ) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP, BCP, ex 1 and ex 2 are as follows.

[ Comparative Example  1 to 3] green organic Field  Fabrication of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that ex1, ex2, and CBP were used instead of Compound A-1 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  One]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1 to 21 and Comparative Examples 1 to 3, .

Sample Host Driving voltage EL peak Current efficiency (V) (nm) (cd / A) Example 1 A-1 6.20 518 44.8 Example 2 A-9 6.18 518 44.9 Example 3 A-13 6.46 518 41.3 Example 4 A-1-1 6.7 517 41.3 Example 5 A-2-1 6.72 515 43.1 Example 6 A-3-1 6.22 518 45.1 Example 7 A-3-14 6.66 518 41.4 Example 8 B-13 6.32 516 44.5 Example 9 B-21 6.88 518 38.7 Example 10 B-3-1 6.54 518 44.9 Example 11 B-3-13 6.47 518 43.3 Example 12 C-1 6.21 517 43.8 Example 13 C-3-1 6.29 515 43.1 Example 14 E-1 6.27 518 44.7 Example 15 E-2 6.37 518 41.4 Example 16 E-6 6.22 518 42.8 Example 17 E-2-1 6.30 516 42 Example 18 E-2-6 6.24 518 42.9 Example 19 E-3-1 6.60 518 44.8 Example 20 E-3-2 6.58 516 44.1 Example 21 E-3-3 6.73 515 44.9 Comparative Example 1 ex 1 6.90 516 40.3 Comparative Example 2 ex 2 6.52 517 39.8 Comparative Example 3 CBP 6.98 516 38.2

From Table 1, the driving voltage, the emission peak, and the current efficiency of the organic light emitting devices manufactured in Examples 1 to 21 are superior to the driving voltage, the emission peak, and the current efficiency of the organic light emitting devices manufactured in Comparative Examples 1 to 3 Can be confirmed.

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 (13)

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

In Formula 1,
m is an integer from 0 to 4;
n and l are each independently an integer of 0 to 3;
Y ₁ and Y ₂ is a single bond, O, S, Se, N (R ₄₎ and _{C (R 5) (R 6} ) a is selected from the group consisting, with the proviso that Y ₁ and Y ₂ is a single bond at the same time, each independently Not;
L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
X ₁ to X ₄ are each independently N or C (R ₇ ), and one of them is necessarily N;
Any one of X ₁ to X ₄ bonded to L ₂ is C (R ₇ ), wherein R ₇ is a member;
Z ₁ to Z ₃ are each independently N or C (R ₈ ), and one is necessarily N;
Ar ₁ and Ar ₂ 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 ~ C ₆₀ aryl phosphazene group, selected from the group consisting of a C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and an aryl amine of the C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring,
R ₁ to R ₈ 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 ~ aryl phosphazene group of C _60, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C selected from the ₆₀ group consisting of aryl amines, or to combine groups which are adjacent to form a fused ring, wherein R ₁ to R ₈ are plural, they are the same as or different from each other;
The arylene group and the heteroarylene group of L ₁ and L ₂ and the Ar ₁ and Ar ₂ And R ₁ to the alkyl group of R _8, 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. The method according to claim 1,
Wherein the compound is represented by any one of the following formulas (2) to (7):
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 2 to 7,
m, n, l, L ₁ , L _2, R ₁ to R ₆ , X ₁ to X ₄ , Z ₁ to Z _3, Ar ₁ and Ar ₂ are each as defined in claim 1. The method according to claim 1,
The compound is a compound represented by any one of the following formulas (8) to (10): < EMI ID =
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the above formulas (8) to (10)
m, n, l, Y ₁ , Y _2, L ₁ , L _2, R ₁ to R _3, Z ₁ to Z _3, Ar ₁ and Ar ₂ are as defined in claim 1. The method according to claim 1,
Each of R ₁ to R ₆ is 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,
The alkyl, aryl and heteroaryl groups of R ₁ to R ₆ 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. The method according to claim 1,
Wherein L ₁ and L ₂ are each independently a single bond or a linker selected from the group consisting of the following formulas A-1 to A-4:

In the above Formulas A-1 to A-4,
* Means the part where the combination is made. 6. The method of claim 5,
Wherein the linker represented by A-1 is a linker represented by the following formula (B-1) or (B-2):

In the above formula (B-1) or (B-2)
* Means the part where the combination is made. The method according to claim 1,
Each of Ar ₁ and Ar ₂ is 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,
The alkyl, aryl and heteroaryl groups of Ar ₁ and Ar ₂ 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. The method according to claim 1,
Wherein Ar ₁ and Ar ₂ are each independently a substituent represented by any one of the following formulas C-1 to C-5:

In the above formulas C-1 to C-5,
* Denotes the part where the bond is made;
p is an integer from 0 to 5;
q is an integer from 0 to 4;
R ₉ 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 ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ aryl phosphazene group of C _60, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent form a condensed ring, and wherein R ₉ and R < ₁₀ > each are the same or different from each other;
Alkyl group of the R ₉ 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 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 Substituted with one or more substituents being unsubstituted or, if substituted by a plurality of substituents, they are same as or different from each other. 9. The method of claim 8,
Each of R ₉ and R ₁₀ is independently selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms. 9. The method of claim 8,
Wherein the substituent represented by the formula (C-1) is a substituent represented by any one of the following formulas (D-1) to (D-5)

In the above formulas D-1 to D-5,
* Means the part where the bond is made. The method according to claim 1,
Wherein said compound is selected from the group consisting of:

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). 13. The method of claim 12,
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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