KR20180128181A - 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. The compound according to the present invention is used in an organic material layer of the organic electroluminescent device, preferably a light emitting layer, so that the luminous efficiency, the driving voltage and the life of the organic electroluminescent device can be improved.

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, Tang The organic light emitting device having a laminated structure in which the hole layer and the functional layer of the light emitting layer are divided. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

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

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

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

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

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

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

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

[Chemical Formula 1]

In Formula 1,

p is an integer from 0 to 5;

q and r are each independently an integer of 0 to 4;

R ₁ to R ₃ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine blood group and the group consisting of C ₆ ~ with an aryl amine of the C ₆₀ of the R ₁ to R ₃ in each case a plurality of individual, they are equal to each other, or Different;

The 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 of R ₁ to R ₃ 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;

Ar ₁ is a substituent represented by the following formula (2);

(2)

In Formula 2,

* Denotes the part where the bond is made;

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

R ₄ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

Alkyl groups of the L ₁ and L ₂ of the arylene group and a heteroarylene group, wherein R _4, 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 aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

The present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .

&Quot; Halogen " in the present invention means fluorine, chlorine, bromine or iodine.

"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, for example, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, Click 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,

p is an integer from 0 to 5;

q and r are each independently an integer of 0 to 4;

R ₁ to R ₃ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine blood group and the group consisting of C ₆ ~ with an aryl amine of the C ₆₀ of the R ₁ to R ₃ in each case a plurality of individual, they are equal to each other, or Different;

The 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 of R ₁ to R ₃ 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 boronic 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;

Ar ₁ is a substituent represented by the following formula (2);

(2)

In Formula 2,

* Denotes the part where the bond is made;

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

R ₄ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

Alkyl groups of the L ₁ and L ₂ of the arylene group and a heteroarylene group, wherein R _4, 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 aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

The present invention provides a novel fluorene compound excellent in thermal stability, carrier transporting ability, and light emitting ability.

Specifically, the novel organic compound according to the present invention has a structure in which phenyl and indazole are fixed at the 9-position of phenylfluorene to form a basic skeleton, and EWG having excellent electron transporting ability is bonded to this basic skeleton.

The compounds of the present invention are expected to improve efficiency by combining indazole and EWG structures that enhance electron mobility in a fluorene structure having excellent thermal stability and carrier mobility and are expected to interact with an iridium dopant Thereby facilitating energy transfer. As a result, the efficiency of the organic light emitting device can be increased by increasing the performance of the electron transporting layer. Further, the emission efficiency of the device can be improved by contributing to the increase of the number of the excitons as the light emitting layer, and the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased.

In addition, the compound of Formula 1 has a higher molecular weight and a higher glass transition temperature due to introduction of various substituents, especially heteroaryl groups, into the basic skeleton, and thus has a higher thermal stability than conventional electron transport layer materials have. The compound is also effective for inhibiting crystallization of the organic material layer.

As described above, when the compound represented by Formula 1 is applied to an organic material layer of an organic electroluminescent device, preferably an electron transport layer / injection layer material, the performance and lifetime characteristics of the organic electroluminescent device can be improved.

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 (A-1) to (A-6) Or a linker represented by A-1, A-2, A-4, A-5 and A-6:

In the above Formulas A-1 to A-6,

* Means the part where the combination is made.

According to a preferred embodiment of the present invention, R ₄ is 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 ₄ are each independently substituted with at least one substituent 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 ₄ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, A pyridinyl group, a quinolinyl group, an isoquinolinyl group, a cinolinyl group, a quinoxalinyl group, and a quinazolinyl group,

Examples of the R ₄ group include a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, The norbornyl group, the cinnolinyl group, the quinoxalinyl group and the quinazolinyl group 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 ₄ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, A pyridinyl group, a quinolinyl group, an isoquinolinyl group, a cinolinyl group, a quinoxalinyl group, and a quinazolinyl group,

Examples of the R ₄ group include a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, The norbornyl group, the norbornyl group, the norbornyl group, the norbornyl group, the norbornyl group, the norbornyl group, the norbornyl group, the phenanthryl group, Substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen atom, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, They are the same or different from each other.

According to a preferred embodiment of the present invention, R ₄ may be a substituent represented by any of the following formulas (3) to (6):

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 3 to 6,

* Denotes the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₆ );

m is an integer from 0 to 4;

R ₅ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic selected from the group the group consisting of C ₆ ~ with an aryl amine of the C ₆₀ or, by combining groups of neighboring case to form a condensed ring, individual said R ₅ is plural, they Are the same or different from each other;

R ₆ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination tile adjacent case to form a condensed ring, individual said R ₆ is a plurality which the Are the same or different from each other;

Alkyl groups of the R ₅ and R _6, 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 blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 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, the substituent represented by the formula (3) may be a substituent represented by the following formula (7)

(7)

In Formula 7,

* Denotes the part where the bond is made;

R ₇ and R ₈ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, said shed some light selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of;

Alkyl group of the R ₇ and 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 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 blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with a plurality of substituents, they are the same as or different from each other;

Z ₁ , Z ₃ and Z ₅ are as defined in formula (3).

According to a preferred embodiment of the present invention, the substituent represented by the formula (3) may be a substituent represented by any one of the following formulas (B-1) to (B-5)

In the above Formulas B-1 to B-5,

* Denotes the part where the bond is made,

R ₉ and R ₁₀ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl group of the R ₉ and R _10, 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 blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of When they are substituted or unsubstituted with one or more substituents, 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 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 Selected;

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, each of R ₉ and R ₁₀ may independently be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group,

The phenyl, biphenyl, pyridinyl, pyrimidinyl, triazinyl and naphthalenyl groups of R ₉ and R ₁₀ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heteroaryl group;

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ may each independently be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group, Preferably a phenyl group, a biphenyl group, and a pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group of R ₉ and R ₁₀ each independently represents a methyl group, an ethyl group, a butyl group, a propyl group, a pentyl 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, the substituent represented by Formula 6 may be a substituent represented by Formula 8:

[Chemical Formula 8]

In Formula 8,

* Denotes the part where the bond is made,

m and R < ₅ > are as defined in formula (6).

According to a preferred embodiment of the present invention, R ₅ is 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 group, aryl group and heteroaryl group of R ₅ are each independently substituted with at least one substituent 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 ₅ may be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group of R ₅ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heteroaryl group.

According to a preferred embodiment of the present invention, R ₅ may be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group, more preferably a phenyl group, A phenyl group and a pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group of R ₅ are each independently a group consisting of a methyl group, an ethyl group, a butyl group, a propanyl group, a pentyl 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, R ₄ may be a substituent represented by any one of the following formulas C-1 to C-8:

In the above formulas C-1 to C-8,

* Denotes the part where the bond is made;

n is an integer from 0 to 4;

o is an integer from 0 to 3;

R ₁₁ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of aryl amines, or combine tile adjacent case form a condensed ring, and the individual is a R ₁₁ a plurality which the Are the same or different from each other;

Alkyl group of the R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ A C ₆ to C ₆₀ arylphosphonyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁₁ may be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group of R ₁₁ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heteroaryl group.

According to a preferred embodiment of the present invention, R ₁₁ may be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group, A phenyl group and a pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group of R ₁₁ each independently represents a group consisting of a methyl group, an ethyl group, a butyl group, a propanyl group, a pentyl group, , And when they are substituted with a plurality of substituents, they are the same as or different from each other.

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.

One. Organic electroluminescent device

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

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

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

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

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

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

The electron injection layer 36 is a layer which is stacked on the electron transport layer 34 to facilitate injection of electrons from the cathode to ultimately improve power efficiency and is commonly used in the art . For example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, and BaO can be used.

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

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

In the present invention, the compound represented by the formula (1) includes a fluorene-based moiety and has a very excellent electrochemical stability, a high glass transition temperature and carrier transporting ability, and particularly excellent electron and hole transport mobility The balance of the carriers in the light emitting layer exhibits very good properties. The materials represented by Formula 1 are structurally characteristic to be bonded with core core and EWG (electron withdrawing group), and have excellent electron mobility and excellent high glass transition temperature and thermal stability. In addition, the holes and electrons transferred to the light emitting layer have excellent charge balance in the materials having the structure of Formula 1, so that the exciton generation is excellent, and the energy transfer efficiency to the dopant is high, thereby improving the luminous efficiency of the device and improving the durability and stability of the device. So that the lifetime of the device can be efficiently increased. Most of the developed materials exhibit physical characteristics that enable low-voltage operation and thereby improve lifetime.

Therefore, the compound represented by the general formula (1), which is a representative claim structure of the present invention, is excellent in luminescence characteristics, and therefore, it is preferable to use any one of the hole injection layer, the hole transporting layer, the light emitting layer, the electron transporting layer, It can be used as a material. And preferably used as a material for the light emitting layer of blue phosphorescence.

Preferably an electron transporting layer laminated on the light emitting layer, the electron transporting layer and the electron transporting layer of blue phosphorescence. In addition, since the electron transporting layer has high triplet energy, it can exhibit excellent efficiency due to the triplet-triplet fusion (TTF) effect.

Further, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. The number of the excitons contributing to light emission in the light emitting layer can be increased to improve the light emitting efficiency of the device and the durability and stability of the device can be improved and the lifetime of the device can be efficiently increased. Most of the developed materials exhibit physical characteristics that can be driven at low voltage, thereby improving lifetime.

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.

Example

[Preparation Example] Synthesis of Core

<Step 1> Synthesis of (1H-indazol-5-yl) (phenyl) methanone

5-bromo-1H-indazole (100 g, 507.51 mmol) was added to the reactor, 1000 ml of THF was added, and the mixture was stirred and placed in a dry ice bath. The internal temperature was set at -78 ° C. 2.5 M n-BuLi (186 ml, 465.21 mmol) is slowly injected with a syringe and stirred for 30 minutes. benzaldehyde (42.7 g, mmol) is dissolved in 100 ml of THF and then slowly added dropwise. Slowly raise to room temperature. After concentrating the reaction mixture, I ₂ (283.38 g, 1165.25 mmol), K ₂ CO ₃ (280.57.4 g, 2030 mmol) and 800 ml of t-BuOH were added and the mixture was refluxed for 7 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and then filtered with MgSO ₄ .

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 1H-indazol-5-yl) (phenyl) methanone (79 g, yield 70%) was obtained by column chromatography.

¹ H-NMR: 7.48 (m, 3 H) 7.82 (m, 3 H), 8.25

 [LCMS]: 222

<Step 2> Synthesis of [1,1'-biphenyl] -2-yl (1H-indazol-5-yl)

2-bromo-1,1'-biphenyl (99.4 g, 426.54 mmol) was added to the reactor, 500 ml of THF was added, and the mixture was stirred and placed in a dry ice bath. The internal temperature was set at -78 ° C. 2.5 M n-BuLi (156.4 ml, 390.99 mmol) is slowly injected with a syringe and stirred for 30 minutes. Preparation example 1 (1H-indazol-5-yl) (phenyl) methanone (79 g, 355.45 mmol) synthesized in <Step 1> is dissolved in 500 ml of THF and then slowly added dropwise. The temperature is slowly raised to room temperature to terminate the reaction. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and then filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound [1,1'-biphenyl] -2-yl (1H-indazol-5-yl) (phenyl) methanol (85.3 g, yield 64% &Lt; / RTI &gt;

¹ H-NMR:? 6.62 (s, 1 H), 7.25 (m, 7H), 7.48 (m, 7H), 7.85 , 1H)

 [LCMS]: 376

<Step 3> Synthesis of Core

1H-indazol-5-yl) (phenyl) methanol (85.3 g, 226.58 mmol) synthesized in Step 2 was dissolved in 1000 ml of toluene, 20 ml of sulfuric acid was added with stirring. The temperature was raised to 100 캜, stirred for 8 hours, and then cooled to room temperature. Setting. After completion of the reaction, the reaction mixture was extracted with methylene chloride and then filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, Core (58.6 g, yield 72%) was obtained by column chromatography.

¹ H-NMR:? 7.18 (m, 4H), 7.32 (m, 6H), 7.55 (m, 2H), 7.78 1H), 12.15 (s, 1 H)

 [LCMS]: 358

[Synthesis Example 1] Synthesis of Compound Inv 5

(5.0 g, 13.95 mmol) obtained in Step 3 of Preparation Example 1 and 2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1 (0.28 g, 13.95 mmol), sodium tert-butoxide (2.68 g, 0.41 mmol), 3,5-triazine (4.61 g, 16.74 mmol) and Pd (OAc) 27.89 mmol) were added to 80 ml of toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO4. After removing the solvent of the filtered organic layer, Inv 5 (6.8 g, yield 65%) was obtained by column chromatography.

[LCMS]: 741

[Synthesis Example 2] Synthesis of compound Inv 16

2- (4- (4-chloronaphthalen-1-yl) -4,6-diphenyl-1,3,5-triazine was used instead of 2- (3'- phenyl) -4,6-diphenyl-1,3,5-triazine (7.87 g, 16.74 mmol) was used in place of the target compound, Inv 16 (6.3 g, yield 57 %).

[LCMS]: 791

[Synthesis Example 3] Synthesis of Compound Inv 20

([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- Synthesis was carried out except that [4'-chloro- [1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazine (8.3 g, 16.74 mmol) Example 1] was performed to obtain Inv 20 (7.3 g, yield 64%) as a target compound.

[LCMS]: 818

[Synthesis Example 4] Synthesis of compound Inv 23

([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- Synthesis was carried out except that [4'-chloro- [1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazine (8.3 g, 16.74 mmol) Example 1] to obtain Inv 23 (7.0 g, yield 61%) as a target compound.

[LCMS]: 818

[Synthesis Example 5] Synthesis of Compound Inv 38

Instead of 2 - ([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- Synthesis was carried out except that [4'-chloro- [1,1'-biphenyl] -3-yl) -6-phenyl-1,3,5-triazine (8.3 g, 16.74 mmol) Example 1] to obtain Inv 38 (7.2 g, yield 63%) as a target compound.

[LCMS]: 818

[Synthesis Example 6] Synthesis of compound Inv 41

Instead of 2 - ([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- 4-yl) -6-phenyl-1,3,5-triazine (9.57 g, 16.74 mmol) (Inv 41) (7.6 g, yield 61%) was obtained by carrying out the same procedure as in [Synthesis Example 1].

[LCMS]: 894

[Synthesis Example 7] Synthesis of compound In 50

([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- -4-yl) -6- (4-chlorophenyl) -1,3,5-triazine (8.3 g, 16.74 mmol) was used in place of [ 7.5 g, yield 65%).

[LCMS]: 818

[Synthesis Example 8] Synthesis of compound Inv 52

([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- 4-yl) -6- (4'-chloro- [1,1'-biphenyl] -4-yl) -1,3,5-triazine (9.57 g, 16.74 mmol) 1], the desired compound Inv 52 (7.9 g, yield 63%) was obtained.

[LCMS]: 894

[Synthesis Example 9] Synthesis of compound Inv 67

2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine 2 - ([1,1'-biphenyl] [Synthesis Example 1 (Synthesis Example 1)] was repeated except for using 4 - ([1,1'-biphenyl] -4-yl) -6- (3-chlorophenyl) ] To obtain Inv 67 (7.1 g, yield 62%) as a target compound.

[LCMS]: 818

[Synthesis Example 10] Synthesis of Compound Inv 71

Instead of 2 - ([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- yl) -4 - ([1,1'-biphenyl] -4-yl) -6- (3'-chloro- [1,1'-biphenyl] -3-yl) -1,3,5-triazine 9.57 g, 16.74 mmol) was used in place of the compound obtained in Synthesis Example 1 to obtain the desired compound, Inv 71 (5.6 g, yield 74%).

[LCMS]: 894

[Synthesis Example 11] Synthesis of Compound Inv 86

([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- 3-yl) -6- (4'-chloro- [1,1'-biphenyl] -3-yl) -1,3,5-triazine (9.57 g, 16.74 mmol) 1], the desired compound Inv 86 (7.4 g, yield 59%) was obtained.

[LCMS]: 894

 [Synthesis Example 12] Synthesis of Compound Inv90

([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- -3-yl) -6- (4 "-chloro- [1,1 ': 3', 1" -terphenyl] -4-yl) -1,3,5-triazine (10.85 g, 16.74 mmol) The same procedure as in [Synthesis Example 1] was repeated to obtain Inv 90 (8.2 g, yield 60%) as a target compound.

[LCMS]: 970

[Synthesis Example 13] Synthesis of Compound Inv 98

6 '- (4-chlorophenyl) -3,2': (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl- Inv 98 (5.8 g, yield 62%) was obtained in the same manner as in [Synthesis Example 1], except that 4 ', 3' '- terpyridine (5.75 g, 16.74 mmol) was used.

[LCMS]: 970

[Synthesis Example 14] Synthesis of Compound Inv105

6 '- (3 "-chloro- [1,1'-biphenyl] -4-yl) The same procedure as in [Synthesis Example 1] was repeated except that 4 ', 4', 1 "-terphenyl] -4-yl) -3,2 ': 4', 3" -terpyridine (8.3 g, 16.74 mmol) To obtain Inv 105 (6.8 g, yield 60%) as a target compound.

[LCMS]: 818

[Synthesis Example 15] Synthesis of Compound Inv 116

Instead of 2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- 4-yl) -4,6-diphenylpyrimidine (7.0 g, 16.74 mmol) was used in place of [ .

[LCMS]: 740

[Synthesis Example 16] Synthesis of compound Inv 127

Substituting 2- (4'-chloro- [1,1 '-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- 3-yl) -4,6-diphenylpyrimidine (8.28 g, 16.74 mmol) was used in place of the target compound, Inv 127 7.4 g, yield 65%).

[LCMS]: 817

[Synthesis Example 17] Synthesis of Compound Inv 134

Substituting 4- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- biphenyl] -3-yl) -2,6-diphenylpyrimidine (7.0 g, 16.74 mmol) was used in the same manner as in [Synthesis Example 1] to obtain the desired compound Inv 134 (6.7 g, yield 65%) .

[LCMS]: 740

[Synthesis Example 18] Synthesis of Compound Inv 141

Substituting 4- (3 &quot; -chloro- [1,1 '-biphenyl] -4-yl) -4,6-diphenyl- The same procedure as in [Synthesis Example 1] was repeated but using Inv 141 (4 ', 1 "-terphenyl] -3-yl) -2,6-diphenylpyrimidine (8.28 g, 16.74 mmol) 7.1 g, yield 62%).

[LCMS]: 817

[Synthesis Example 19] Synthesis of Compound Inv 146

4 - ([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine in place of 2- (3'- Inv 146 (6.7 g, yield 65%) was obtained by carrying out the same processes as in [Synthesis Example 1] except that 2- (4-chlorophenyl) -6-phenylpyrimidine (7.0 g, 16.74 mmol) &Lt; / RTI &gt;

[LCMS]: 740

[Synthesis Example 20] Synthesis of Compound Inv 150

4 - ([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine in place of 2- (3'- yl] -6-phenylpyrimidine (8.28 g, 16.74 mmol) was used in place of 4- (4'-chloro- [1,1'-biphenyl] To obtain Inv 150 (7.7 g, yield 67%) as a target compound.

[LCMS]: 817

[Synthesis Example 21] Synthesis of Compound Inv 164

4 - ([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine in place of 2- (3'- yl] -2-phenylpyrimidine (8.28 g, 16.74 mmol) was used in place of 4- (4'-chloro- [1,1'-biphenyl] -4-yl) To obtain the desired compound Inv 164 (7.5 g, yield 65%).

[LCMS]: 817

[Synthesis Example 22] Synthesis of compound Inv 167

4 - ([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine in place of 2- (3'- yl] -6- (3'-chloro- [1,1'-biphenyl] -3-yl) -2-phenylpyrimidine (8.28 g, 16.74 mmol) was used in place of [ To obtain the target compound Inv 167 (7.7 g, yield 66%).

[LCMS]: 817

[Synthesis Example 23] Synthesis of compound Inv 180

Substituting 4- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- biphenyl] -4-yl) -2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (8.3 g, 16.74 mmol) The target compound Inv 180 (7.6 g, yield 74%) was obtained.

[LCMS]: 818

[Synthesis Example 24] Synthesis of compound Inv 188

4- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- [Synthesis Example 1 (Synthesis Example 1)] was repeated except for using 4,5 ', 4', 1 "-terphenyl] -3-yl) -2-phenyl- ] To obtain the desired compound Inv 188 (7.8 g, yield 62%).

[LCMS]: 894

[Synthesis Example 25] Synthesis of compound Inv 204

2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine 2- (4'-chloro- [1,1'- ] -4-yl) -6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine (7.66 g, 16.74 mmol) To obtain Inv 204 (6.7 g, yield 61%) as a target compound.

[LCMS]: 779

[Synthesis Example 26] Synthesis of compound Inv 219

Instead of 2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- biphenyl] -4-yl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (8.53 g, 16.74 mmol) 1], the desired compound Inv 219 (7.1 g, yield 61%) was obtained.

[LCMS]: 831

[Synthesis Example 27] Synthesis of compound Inv 227

Instead of 2 - ([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5- dibenzo [b, d] furan-4-yl) -1,3,5-triazine (8.53 g, 16.74 mmol) was used instead of 4- ], The target compound Inv 227 (7.4 g, yield 63%) was obtained.

[LCMS]: 831

[Synthesis Example 28] Synthesis of compound Inv 252

2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine 2- (4'-chloro- [1,1'- ] -4-yl) -4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine (10.04 g, 16.74 mmol) , The target compound Inv 252 (7.5 g, yield: 58%) was obtained.

[LCMS]: 846

[Synthesis Example 29] Synthesis of compound Inv 264

2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine 2- (3'-chloro- [1,1'- 3-yl) -4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (8.53 g, 16.74 mmol) ] To obtain the target compound Inv 264 (7.2 g, yield 62%).

[LCMS]: 831

[Synthesis Example 30] Synthesis of compound Inv 277

([1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- Synthesis Example 1] was repeated except for using 4-chloro- benzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (8.53 g, 16.74 mmol) The same procedure was followed to obtain the desired compound Inv 277 (6.8 g, yield 58%).

[LCMS]: 831

[Examples 1 to 30] Fabrication of blue organic electroluminescent device

The compounds Inv 5 to Inv 277 synthesized in the synthesis examples were subjected to high purity sublimation purification by a conventionally known method, and blue organic electroluminescent devices were prepared as follows.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) The substrate was transferred to a vacuum evaporator.

 NPN (15 nm) / ADN + 5% DS-405 (Doosan Electronics Co., 30 nm) / Compound Inv 5 to Inv 277 (30 nm) on a prepared ITO transparent electrode nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[Comparative Example 1] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that Alq3 was used instead of Compound Inv5 as the electron transport layer material.

 [Comparative Example 2] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that the compound Inv 5 was not used as the electron transport layer material.

 The structures of NPB, AND and Alq3 used in Examples 1 to 30 and Comparative Examples 1 and 2

Is as follows.

[Evaluation Example 1]

Current efficiency and emission peak at current density (10) mA / cm &lt; 2 &gt; were measured for each of the blue organic electroluminescent devices manufactured in Examples 1 to 30 and Comparative Examples 1 and 2, Respectively.

Sample material Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 Inv 5 3.4 458 7.0 Example 2 Inv 16 4.6 459 7.1 Example 3 Inv 20 4.1 458 6.8 Example 4 Inv 23 4.0 455 6.9 Example 5 Inv 38 4.6 456 6.7 Example 6 Inv 41 3.2 457 6.7 Example 7 Inv 50 3.9 456 6.9 Example 8 Inv 52 3.8 452 7.2 Example 9 Inv 67 3.6 448 6.9 Example 10 Inv 71 3.7 460 7.4 Example 11 Inv 86 3.2 455 6.8 Example 12 Inv 90 3.6 456 6.9 Example 13 Inv 98 3.9 457 6.9 Example 14 Inv 105 3.9 452 6.8 Example 15 Inv 116 3.3 448 6.7 Example 16 Inv 127 3.6 460 6.8 Example 17 Inv 134 3.5 465 6.9 Example 18 Inv 141 3.9 457 6.8 Example 19 Inv 146 3.8 456 7.0 Example 20 Inv 150 4.1 465 6.8 Example 21 Inv 164 3.6 457 7.2 Example 22 Inv 167 3.6 456 6.9 Example 23 Inv 180 3.2 457 7.1 Example 24 Inv 188 3.2 456 6.8 Example 25 Inv 204 4.1 455 6.7 Example 26 Inv 219 3.6 459 6.8 Example 27 Inv 227 3.7 461 6.9 Example 28 Inv 252 3.9 464 7.1 Example 29 Inv 264 3.6 467 7.2 Example 30 Inv 277 3.8 467 6.9 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 1 above, the compound of the present invention was used in the electron transport layer

Compared to the blue organic electroluminescent device (Comparative Example 1) using conventional Alq3 as the electron transport layer and the blue organic electroluminescent device without the electron transport layer (Comparative Example 2), the blue organic electroluminescent devices (Examples 1 to 30) , The emission peak, and the current efficiency.

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 (14)

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

In Formula 1,
p is an integer from 0 to 5;
q and r are each independently an integer of 0 to 4;
R ₁ to R ₃ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine blood group and the group consisting of C ₆ ~ with an aryl amine of the C ₆₀ of the R ₁ to R ₃ in each case a plurality of individual, they are equal to each other, or Different;
The 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 of R ₁ to R ₃ 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 boronic 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;
Ar ₁ is a substituent represented by the following formula (2);
(2)

In Formula 2,
* Denotes the part where the bond is made;
L ₁ and L ₂ are each independently selected from the group consisting of a direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
R ₄ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;
Alkyl groups of the L ₁ and L ₂ of the arylene group and a heteroarylene group, wherein R _4, 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 aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of the following formulas A-1 to A-6:

In the above Formulas A-1 to A-6,
* Means the part where the combination is made. The method according to claim 1,
Wherein R ₄ is 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 ₄ are each independently substituted with at least one substituent 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 R &lt; ₄ &gt; is a substituent represented by any one of the following formulas (3) to (6)
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 3 to 6,
* Denotes the part where the bond is made;
Z ₁ to Z ₅ are each independently N or C (R ₆ );
m is an integer from 0 to 4;
R ₅ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic selected from the group the group consisting of C ₆ ~ with an aryl amine of the C ₆₀ or, by combining groups of neighboring case to form a condensed ring, individual said R ₅ is plural, they Are the same or different from each other;
R ₆ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination tile adjacent case to form a condensed ring, individual said R ₆ is a plurality which the Are the same or different from each other;
Alkyl groups of the R ₅ and R _6, 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 blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 And when they are substituted with a plurality of substituents, they are the same as or different from each other. 5. The method of claim 4,
Wherein the substituent represented by Formula 3 is a substituent represented by Formula 7:
(7)

In Formula 7,
* Denotes the part where the bond is made;
R ₇ and R ₈ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, said shed some light selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of;
Alkyl group of the R ₇ and 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 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 blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with a plurality of substituents, they are the same as or different from each other;
Z ₁ , Z ₃ and Z ₅ are as defined in claim 4. 5. The method of claim 4,
Wherein the substituent represented by the general formula (3) is a substituent represented by any one of the following general formulas (B-1) to (B-5):

In the above Formulas B-1 to B-5,
* Denotes the part where the bond is made,
R ₉ and R ₁₀ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
Alkyl group of the R ₉ and R _10, 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 blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of When they are substituted or unsubstituted with one or more substituents, 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 6,
Each of R ₉ and R ₁₀ 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 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. 5. The method of claim 4,
Wherein the substituent represented by Formula 6 is a substituent represented by Formula 8:
[Chemical Formula 8]

In Formula 8,
* Denotes the part where the bond is made,
m and R &lt; ₅ &gt; are as defined in claim 4. 9. The method of claim 8,
The R ₅ is 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 group, aryl group and heteroaryl group of R ₅ are each independently substituted with at least one substituent 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 R &lt; ₄ &gt; is a substituent represented by any one of the following formulas C-1 to C-8:

In the above formulas C-1 to C-8,
* Denotes the part where the bond is made;
n is an integer from 0 to 4;
o is an integer from 0 to 3;
R ₁₁ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of aryl amines, or combine tile adjacent case form a condensed ring, and the individual is a R ₁₁ a plurality which the Are the same or different from each other;
Alkyl group of the R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ A C ₆ to C ₆₀ arylphosphonyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, And when they are substituted with a plurality of substituents, they are the same as or different from each other. 11. The method of claim 10,
Wherein R ₁₁ is 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. 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). 14. The method of claim 13,
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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