KR102358032B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

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

Description

Organic compound and organic electroluminescent device comprising the same

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

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

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

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

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

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

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

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

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

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

[Formula 1]

In Formula 1,

p is an integer from 0 to 5;

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

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

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

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

[Formula 2]

In Formula 2,

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

R ₄ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha a nyl group, a C ₆ -C ₆₀ mono- or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

The arylene group and heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, aryl of R ₄ An amine group, an alkylsilyl group, an alkylboron group, an arylboron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When substituted with one or more substituents selected from the group consisting of an arylsilyl group, or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

The present invention provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer includes the compound of Formula 1 .

"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, and hexyl. and the like, but is not limited thereto.

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

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

“Aryl” in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, in which a single ring or two or more rings are combined. In addition, two or more rings are condensed with each other, contain only carbon as a ring-forming atom (eg, the number of carbon atoms may be 8 to 60), and the whole molecule is monovalent having non-aromaticity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. In this case, at least one carbon, preferably 1 to 3 carbons in the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply attached to or condensed with each other, and contain a hetero atom selected from N, O, P, S and Se in addition to carbon as a ring forming atom, and the entire molecule is non-aromatic (non-aromatic). It is interpreted to include a monovalent group having aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycylates such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl click ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

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

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

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

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

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

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

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

Since the compound of the present invention has excellent thermal stability, carrier transport ability, light emitting ability, etc., it can be usefully applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device comprising the compound of the present invention in an organic material layer has greatly improved aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel.

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

Hereinafter, the present invention will be described in detail.

One. new organic compounds

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

[Formula 1]

In Formula 1,

p is an integer from 0 to 5;

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

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

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

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

[Formula 2]

In Formula 2,

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

R ₄ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha a nyl group, a C ₆ -C ₆₀ mono- or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

The arylene group and heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, aryl of R ₄ An amine group, an alkylsilyl group, an alkylboron group, an arylboron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When substituted with one or more substituents selected from the group consisting of an arylsilyl group, or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

The present invention provides a novel fluorene-based compound having excellent thermal stability, carrier transport 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 9th position of phenyl fluorene to form a basic skeleton, and EWG having excellent electron transport ability is bonded to this basic skeleton.

The compound of the present invention is expected to improve efficiency by combining indazole and EWG structures that increase electron mobility with a fluorene structure with excellent thermal stability and carrier mobility, and expect interaction with the iridium dopant This facilitates energy transfer. Accordingly, it is possible to increase the performance of the electron transport layer to increase the efficiency of the organic electroluminescent device. In addition, by contributing to an increase in the number of excitons as a light emitting layer, the luminous efficiency of the device may be improved, and durability and stability of the device may be improved, thereby effectively increasing the lifetime of the device.

In addition, in the compound of Formula 1, various substituents, particularly heteroaryl groups, are introduced into the basic skeleton, thereby significantly increasing the molecular weight of the compound, and thus the glass transition temperature is improved to have high thermal stability compared to conventional electron transport layer materials. have. In addition, the compound is effective in inhibiting crystallization of the organic layer.

As such, when the compound represented by Formula 1 in the present invention is applied as an organic material layer material, preferably an electron transport layer/injection layer material, of an organic electroluminescent device, the performance and lifespan 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 Formulas A-1 to A-6, more preferably a direct bond. Or it may be a linker represented by A-1, A-2, A-4, A-5 and A-6:

In Formulas A-1 to A-6,

* means the part where the bond is made.

According to a preferred embodiment of the present invention, R ₄ is selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms,

The alkyl group, aryl group and heteroaryl group of R ₄ are each independently one or more substituents selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₄ is a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a naphthalenyl group, triazolo It is selected from the group consisting of a pyridinyl group, a quinolinyl group, an isoquinolinyl group, a cinolinyl group, a quinoxalinyl group and a quinazolinyl group,

_A methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a naphthalenyl group, a triazolopyridinyl group, a quinolinyl group, isoqui Nolinyl group, cinolinyl group, quinoxalinyl group and quinazolinyl group are each independently selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms When substituted or unsubstituted with more than one kind of substituent, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₄ is a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a naphthalenyl group, triazolo It is selected from the group consisting of a pyridinyl group, a quinolinyl group, an isoquinolinyl group, a cinolinyl group, a quinoxalinyl group and a quinazolinyl group,

_A methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a naphthalenyl group, a triazolopyridinyl group, a quinolinyl group, isoqui Nolinyl group, cinolinyl group, quinoxalinyl group and quinazolinyl group are each independently a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, naphthale substituted with one or more substituents selected from the group consisting of a nyl group, a triazolopyridinyl group, a quinolinyl group, an isoquinolinyl group, a cinolinyl group, a quinoxalinyl group, and a quinazolinyl group, unsubstituted or substituted with a plurality of substituents case, 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 one of the following Chemical Formulas 3 to 6:

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 3 to 6,

* means the part where the bond is formed;

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 group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group is selected from the group, or combined with an adjacent group to form a condensed ring, and when R ₅ is a plurality of these are the same or different from each other;

R ₆ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group is selected from the group, or combined with an adjacent group to form a condensed ring, and when R ₆ is a plurality of these are the same or different from each other;

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

According to a preferred embodiment of the present invention, the substituent represented by the formula (3) may be a substituent represented by the following formula (7):

[Formula 7]

In Formula 7,

* means the part where the bond is formed;

R ₇ and R ₈ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an aryl of R ₇ and R ₈ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted and substituted with a plurality of substituents, they are the same 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 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,

* means the part where the bond is made,

R ₉ and R ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, aryl of the R ₉ and R ₁₀ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms from the group consisting of is selected;

The alkyl group, aryl group and heteroaryl group of R ₉ and R ₁₀ are each independently selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. When substituted or unsubstituted with more than one kind of substituent, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ may be each independently 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 ₉ and R ₁₀ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and nuclear atom When substituted with one or more substituents selected from the group consisting of 5 to 60 heteroaryl groups or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, 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, and more Preferably, it may be selected from the group consisting of 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 are each independently a methyl group, an ethyl group, a butyl group, a propanyl group, a pentyl group, a phenyl group, and a biphenyl group When substituted with one or more substituents selected from the group consisting of or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by the formula (6) may be a substituent represented by the following formula (8):

[Formula 8]

In Formula 8,

* means 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 ~ C ₄₀ alkyl group, a C ₆ ~ 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 selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. One or more substituents When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, 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 ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to When substituted with one or more substituents selected from the group consisting of 60 heteroaryl groups or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, 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 non It may be selected from the group consisting of 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 methyl group, an ethyl group, a butyl group, a propanyl group, a pentyl group, a phenyl group and a biphenyl group When substituted with one or more substituents selected from or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, 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,

* means the part where the bond is formed;

n is an integer from 0 to 4;

o is an integer from 0 to 3;

R ₁₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group is selected from the group, or combined with an adjacent group to form a condensed ring, and when R ₁₁ is a plurality of these are the same or different from each other;

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

According to a preferred embodiment of the present invention, 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, C ₆ to C ₆₀ aryl group and 5 to When substituted with one or more substituents selected from the group consisting of 60 heteroaryl groups or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, 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, more preferably a phenyl group, a non It may be selected from the group consisting of a phenyl group and a pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and naphthalenyl group of R ₁₁ are each independently a methyl group, an ethyl group, a butyl group, a propanyl group, a pentyl group, a phenyl group and a biphenyl group When substituted with one or more substituents selected from or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

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

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

One. organic electroluminescent device

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

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

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

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

Referring to FIG. 2 as another example of the present invention, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10 , and the electron transport layer 34 and the cathode An electron injection layer 36 may be further included between (20).

In the present invention, the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 improves the interfacial properties between ITO used as the anode and the organic material used as the hole transport layer 31 as well. Rather, it is a layer that is applied on top of ITO whose surface is not flat and has a function of making the surface of ITO soft, and it can be used without particular limitation as long as it is commonly used in the art, for example, an amine compound can be used. The present invention is not limited thereto.

In addition, the electron injection layer 36 is laminated on the electron transport layer 34 to facilitate the injection of electrons from the cathode to ultimately improve power efficiency, and is commonly used in the art. As long as it can be used without any particular limitation, for example, a material such as LiF, Liq, NaCl, CsF, Li ₂ O, BaO may be used.

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

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

In the present invention, the compound represented by Formula 1 has excellent electrochemical stability including a fluorene-based moiety, high glass transition temperature and excellent carrier transport ability, and in particular, electron and hole transport mobility is very excellent. The balance of carriers in the light emitting layer exhibits very good characteristics. The materials represented by Chemical Formula 1 are structurally characterized in that they are combined with a core core and an electron-withdrawing group (EWG), and have excellent electron mobility as well as 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 of the formula (1), and thus the generation of excitons is excellent. Thus, the lifespan of the device can be effectively increased. Most of the developed materials exhibit physical characteristics that enable low-voltage operation and improve lifespan.

For this reason, since the compound represented by Formula 1, which is the representative claimed structure of the present invention, has excellent light emitting properties, any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic layers of an organic electroluminescent device material can be used. Preferably, it can be used as a material for the blue phosphorescent light emitting layer.

Preferably, it may be used as any one of the blue phosphorescent light emitting layer, the electron transport layer, and the electron transport auxiliary layer that is further laminated on the electron transport layer. In addition, since it has a high triplet energy as the role of the electron transport auxiliary layer, excellent efficiency increase due to the triplet-triplet fusion (TTF) effect may be exhibited.

In addition, it is possible to prevent the excitons generated in the emission layer from diffusing into the electron transport layer or the hole transport layer adjacent to the emission layer. The number of excitons contributing to light emission in the light emitting layer may be increased to improve luminous efficiency of the device, and durability and stability of the device may be improved to effectively increase the lifetime of the device. Most of the developed materials exhibit physical characteristics that improve lifespan due to low-voltage operation.

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

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

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

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

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

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

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

Example

[Preparation example] Core synthesis

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

Put 5-bromo-1H-indazole (100 g, 507.51 mmol) in the reactor, and then pour 1000 ml of THF and put it in a dry ice bath with stirring, and set the internal temperature to -78 ℃. 2.5M n-BuLi (186 ml, 465.21 mmol) was slowly injected with a syringe and stirred for 30 minutes. After dissolving benzaldehyde (42.7 g, mmol) in 100 ml of THF, it is slowly added dropwise. Slowly raise the temperature to room temperature. After concentrating the reaction, I ₂ (283.38 g, 1165.25 mmol), K ₂ CO ₃ (280.57.4 g, 2030 mmol), 800 ml of t-BuOH were added and heated to reflux for 7 hours. After completion of the reaction, extraction was performed with ethyl acetate, and then MgSO ₄ was added and filtered.

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

¹ H-NMR: 7.48 (m, 3H) 7.82 (m, 3H), 8.25 (s, 1H), 8.45 (d, 1H), 12.05 (s, 1H)

[LCMS]: 222

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

Put 2-bromo-1,1'-biphenyl (99.4 g, 426.54 mmol) in the reactor, 500 ml of THF, and then put into a dry ice bath with stirring, and set the internal temperature to -78 ℃. 2.5M n-BuLi (156.4 ml, 390.99 mmol) was 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> was dissolved in 500ml of THF and slowly added dropwise. The reaction is terminated by slowly raising the temperature to room temperature. After completion of the reaction, extraction was performed with ethyl acetate, and then MgSO ₄ was added and filtered. 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%) was used by column chromatography. got

¹ H-NMR: δ 6.62 (s, 1H), 7.25 (m, 7H), 7.48 (m, 7H), 7.85 (m, 2H) 8.22 (s, 1H), 8.38 (d, 1H), 12.12 (s) , 1H)

[LCMS]: 376

<Step 3> Core synthesis

[1,1'-biphenyl]-2-yl(1H-indazol-5-yl)(phenyl)methanol (85.3 g, 226.58 mmol) synthesized in <Step 2> in the reactor was dissolved in 1000ml of toluene, and then vigorously With stirring, 20 ml of sulfuric acid was added. The temperature was raised to 100 °C, stirred for 8 hours, and then cooled to room temperature. set After completion of the reaction, extraction was performed with methylene chloride, and then MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the target compound, Core (58.6 g, yield 72%) was obtained by column chromatography.

¹ H-NMR: δ 7.18 (m, 4H), 7.32 (m, 6H), 7.55 (m, 2H), 7.78 (s, 1H) 7.9 (m, 2H), 8.18 (s, 1H), 8.32 (d) 1H), 12.15(s, 1H)

[LCMS]: 358

[Synthesis Example 1] Synthesis of compound Inv 5

Core (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 ,3,5-triazine (4.61 g, 16.74 mmol) and Pd(OAc)2 (0.094 g, 0.41 mmol), P(t-Bu)3 (0.28 g, 13.95 mmol), sodium tert-butoxide (2.68 g, 27.89 mmol) was added to 80 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and the mixture was filtered. After removing the solvent of the filtered organic layer, the target compound 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) instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine phenyl)-4,6-diphenyl-1,3,5-triazine (7.87 g 16.74 mmol) was carried out in the same manner as in [Synthesis Example 1] except that the target compound Inv 16 (6.3 g, yield 57) %) was obtained.

[LCMS] : 791

[Synthesis Example 3] Synthesis of compound Inv 20

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-4- yl)-4-(4'-chloro-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (8.3 g 16.74 mmol) [synthesis Example 1] was followed to obtain the target compound, Inv 20 (7.3 g, yield 64%).

[LCMS]: 818

[Synthesis Example 4] Synthesis of compound Inv 23

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-4- yl)-4-(4'-chloro-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (8.3 g 16.74 mmol) [synthesis Example 1] was performed to obtain the target compound Inv 23 (7.0 g, yield 61%).

[LCMS]: 818

[Synthesis Example 5] Synthesis of compound Inv 38

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3- [Synthesis] Except for using yl)-4-(4'-chloro-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine (8.3 g 16.74 mmol) In the same manner as in Example 1], the target compound Inv 38 (7.2 g, yield 63%) was obtained.

[LCMS]: 818

[Synthesis Example 6] Synthesis of compound Inv 41

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3- yl)-4-(3''-chloro-[1,1':4',1''-terphenyl]-4-yl)-6-phenyl-1,3,5-triazine (9.57g 16.74mmol) The same procedure as in [Synthesis Example 1] was performed except that , to obtain the target compound Inv 41 (7.6 g, yield 61%).

[LCMS] : 894

[Synthesis Example 7] Synthesis of compound In 50

2,4-di([1,1'-biphenyl] instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine -4-yl)-6-(4-chlorophenyl)-1,3,5-triazine (8.3g 16.74mmol) was performed in the same manner as in [Synthesis Example 1], except that 7.5 g, yield 65%) was obtained.

[LCMS]: 818

[Synthesis Example 8] Synthesis of compound Inv 52

2,4-di([1,1'-biphenyl] instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine -4-yl)-6-(4'-chloro-[1,1'-biphenyl]-4-yl)-1,3,5-triazine (9.57g 16.74mmol) [Synthesis Example] 1] to obtain the target compound, Inv 52 (7.9 g, yield 63%).

[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]-3-yl )-4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-1,3,5-triazine (8.3 g 16.74 mmol) [Synthesis Example 1 ] to obtain the target compound Inv 67 (7.1 g, yield 62%).

[LCMS]: 818

[Synthesis Example 10] Synthesis of compound Inv 71

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3- yl)-4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-3-yl)-1,3,5-triazine ( 9.57g 16.74mmol) was carried out in the same manner as in [Synthesis Example 1], except that the target compound Inv 71 (5.6 g, yield 74%) was obtained.

[LCMS] : 894

[Synthesis Example 11] Synthesis of compound Inv86

2,4-di([1,1'-biphenyl] instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine -3-yl)-6-(4'-chloro-[1,1'-biphenyl]-3-yl)-1,3,5-triazine (9.57g 16.74mmol) [Synthesis Example] 1] to obtain the target compound, Inv 86 (7.4 g, yield 59%).

[LCMS] : 894

[Synthesis Example 12] Synthesis of compound Inv90

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

[LCMS] : 970

[Synthesis Example 13] Synthesis of compound Inv 98

6'-(4-chlorophenyl)-3,2' instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine: The same procedure as in [Synthesis Example 1] was performed except that 4',3''-terpyridine (5.75 g 16.74 mmol) was used to obtain the target compound, Inv 98 (5.8 g, yield 62%).

[LCMS] : 970

[Synthesis Example 14] Synthesis of compound Inv 105

6'-(3''-chloro-[1,1) instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine The same procedure as [Synthesis Example 1] except that ':4',1''-terphenyl]-4-yl)-3,2':4',3''-terpyridine (8.3 g 16.74 mmol) was used was carried out to obtain the target compound, Inv 105 (6.8 g, yield 60%).

[LCMS]: 818

[Synthesis Example 15] Synthesis of compound Inv 116

2-(4'-chloro-[1,1'- instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine) Biphenyl]-4-yl)-4,6-diphenylpyrimidine (7.0g 16.74mmol) was performed in the same manner as in [Synthesis Example 1], except that the target compound Inv 116 (6.5 g, yield 63%) was obtained. got it

[LCMS]: 740

[Synthesis Example 16] Synthesis of compound Inv 127

2-(4'-chloro-[1,1' instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine) : 3',1''-terphenyl]-3-yl)-4,6-diphenylpyrimidine (8.28g 16.74mmol) was carried out in the same manner as in [Synthesis Example 1] except that the target compound Inv 127 ( 7.4 g, yield 65%) was obtained.

[LCMS]: 817

[Synthesis Example 17] Synthesis of compound Inv 134

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 4-(4'-chloro-[1,1'- Biphenyl]-3-yl)-2,6-diphenylpyrimidine (7.0g 16.74mmol) was performed in the same manner as in [Synthesis Example 1] except that the target compound Inv 134 (6.7 g, yield 65%) was obtained. got it

[LCMS]: 740

[Synthesis Example 18] Synthesis of compound Inv 141

4-(3'-chloro-[1,1' instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine) : 4',1''-terphenyl]-3-yl)-2,6-diphenylpyrimidine (8.28g 16.74mmol) was performed in the same manner as in [Synthesis Example 1], except that the target compound Inv 141 ( 7.1 g, yield 62%) was obtained.

[LCMS]: 817

[Synthesis Example 19] Synthesis of compound Inv 146

4-([1,1'-biphenyl]-4- instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine The same procedure as in [Synthesis Example 1] was performed except that yl)-2-(4-chlorophenyl)-6-phenylpyrimidine (7.0 g 16.74 mmol) was used, and the target compound Inv 146 (6.7 g, yield 65%) was performed. got

[LCMS]: 740

[Synthesis Example 20] Synthesis of compound Inv 150

4-([1,1'-biphenyl]-4- instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine The same procedure as in [Synthesis Example 1] was performed except that yl)-2-(4'-chloro-[1,1'-biphenyl]-3-yl)-6-phenylpyrimidine (8.28g 16.74mmol) was used. to obtain the target compound, Inv 150 (7.7 g, yield 67%).

[LCMS]: 817

[Synthesis Example 21] Synthesis of compound Inv 164

4-([1,1'-biphenyl]-4- instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine The same procedure as in [Synthesis Example 1] was performed except that yl)-6-(4'-chloro-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine (8.28g 16.74mmol) was used. Thus, the target compound Inv 164 (7.5 g, yield 65%) was obtained.

[LCMS]: 817

[Synthesis Example 22] Synthesis of compound Inv 167

4-([1,1'-biphenyl]-4- instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine The same procedure as in [Synthesis Example 1] was performed except that yl)-6-(3'-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine (8.28g 16.74mmol) was used. Thus, the target compound Inv 167 (7.7 g, yield 66%) was obtained.

[LCMS]: 817

[Synthesis Example 23] Synthesis of compound Inv 180

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 4-(4'-chloro-[1,1'- Biphenyl]-4-yl)-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine (8.3g 16.74mmol) was performed in the same manner as in [Synthesis Example 1], except that The target compound, Inv 180 (7.6 g, yield 74%) was obtained.

[LCMS]: 818

[Synthesis Example 24] Synthesis of compound Inv 188

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine 4-(4'-chloro-[1,1': Except for using 4',1''-terphenyl]-3-yl)-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine (9.57g 16.74mmol) [Synthesis Example 1 ] to obtain the target 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'-biphenyl) ]-4-yl)-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine (7.66g 16.74mmol) was followed by the same procedure as in [Synthesis Example 1] The target compound, Inv 204 (6.7 g, yield 61%) was obtained.

[LCMS]: 779

[Synthesis Example 26] Synthesis of compound Inv 219

2-(4'-chloro-[1,1'- instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine) [Synthesis Example] Except for using biphenyl]-4-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (8.53g 16.74mmol) 1] to obtain the target compound Inv 219 (7.1 g, yield 61%).

[LCMS]: 831

[Synthesis Example 27] Synthesis of compound Inv 227

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-3- [Synthesis Example 1] Except that yl)-4-(4-chlorophenyl)-6-(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (8.53g 16.74mmol) was used ] to obtain the target compound, Inv 227 (7.4 g, yield 63%).

[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'-biphenyl) [Synthesis Example 1] except that ]-4-yl)-4,6-bis(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (10.04g 16.74mmol) was used In the same manner as described above, 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'-biphenyl) ]-3-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (8.53g 16.74mmol) [Synthesis Example 1] ] to obtain the target compound, Inv 264 (7.2 g, yield 62%).

[LCMS]: 831

[Synthesis Example 30] Synthesis of compound Inv 277

2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-([1,1'-biphenyl]-4- [Synthesis Example 1] and [Synthesis Example 1] except that yl)-4-(7-chlorodibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (8.53g 16.74mmol) was used The same procedure was followed to obtain the target compound, Inv 277 (6.8 g, yield 58%).

[LCMS]: 831

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

Compounds Inv 5 to Inv 277 synthesized in Synthesis Examples were subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (Doosan Electronics, 30 nm)/Compound Inv 5 ~ Inv 277 (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate an organic electroluminescent device.

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

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

[Comparative Example 2] Fabrication of a blue organic electroluminescent device

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

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

is as follows.

[Evaluation Example 1]

For each of the blue organic electroluminescent devices manufactured in Examples 1 to 30 and Comparative Examples 1 and 2, the driving voltage, current efficiency and emission peak at a current density (10) mA/cm 2 were measured, and the results are shown in the table below 1 is shown.

Sample material drive 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.

The blue organic electroluminescent device (Examples 1 to 30) has a driving voltage compared to the conventional blue organic electroluminescent device using Alq3 for the electron transport layer (Comparative Example 1) and the blue organic electroluminescent device without the electron transport layer (Comparative Example 2) , it was found that it showed excellent performance in terms of emission peak and current efficiency.

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

Claims (14)

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

In Formula 1,
p is an integer from 0 to 5;
q and r are each independently an integer from 0 to 4;
R ₁ To R ₃ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ of Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ of an arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group, wherein when each of R ₁ to R ₃ is a plurality, they are the same as each other or different;
R ₁ to R ₃ Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron Group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group, and C ₆ ~ C ₆₀ With one or more substituents selected from the group consisting of an arylsilyl group When substituted or unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other;
Ar ₁ is a substituent represented by the following formula (2);
[Formula 2]

In Formula 2,
* means 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 ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;
R ₄ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha a nyl group, a C ₆ -C ₆₀ mono- or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;
The arylene group and heteroarylene group of L ₁ and L ₂ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, aryl of R ₄ An amine group, an alkylsilyl group, an alkylboron group, an arylboron group, an arylphosphanyl group, a mono or diarylphosphinyl group, and an arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ When substituted with one or more substituents selected from the group consisting of an arylsilyl group, or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other. The method of claim 1,
The L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of the following formulas A-1 to A-6, a compound:

In Formulas A-1 to A-6,
* means the part where the bond is made. The method of claim 1,
wherein R ₄ is selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,
The alkyl group, aryl group and heteroaryl group of R ₄ are each independently one or more substituents selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other, the compound. The method of claim 1,
Wherein R ₄ is a substituent represented by any one of the following formulas 3 to 6, the compound:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 3 to 6,
* means the part where the bond is formed;
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 group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group is selected from the group, or combined with an adjacent group to form a condensed ring, and when R ₅ is a plurality of these are the same or different from each other;
R ₆ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group is selected from the group, or combined with an adjacent group to form a condensed ring, and when R ₆ is a plurality of these are the same or different from each other;
An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, aryl of the R ₅ and R ₆ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other. 5. The method of claim 4,
The substituent represented by the formula (3) is a substituent represented by the following formula (7), a compound:
[Formula 7]

In Formula 7,
* means the part where the bond is formed;
R ₇ and R ₈ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group;
An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an aryl of R ₇ and R ₈ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other;
Z ₁ , Z ₃ and Z ₅ are as defined in claim 4. 5. The method of claim 4,
The substituent represented by Formula 3 is a substituent represented by any one of the following Formulas B-1 to B-5, a compound:

In the above formulas B-1 to B-5,
* means the part where the bond is made,
R ₉ and R ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group;
An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, aryl of the R ₉ and R ₁₀ Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ One or more substituents selected from the group consisting of arylsilyl group When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other. 7. The method of claim 6,
wherein R ₉ and R ₁₀ are each independently selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms;
The alkyl group, aryl group and heteroaryl group of R ₉ and R ₁₀ are each independently selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. substituted or unsubstituted with more than one substituent, and when substituted with a plurality of substituents, they are the same or different from each other. 5. The method of claim 4,
The substituent represented by the formula (6) is a substituent represented by the following formula (8), a compound:
[Formula 8]

In Formula 8,
* means the part where the bond is made,
m and R ₅ are as defined in claim 4. 9. The method of claim 8,
wherein R ₅ is selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ 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 one or more substituents selected from the group consisting of a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. When substituted with or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other, the compound. The method of claim 1,
Wherein R ₄ is a substituent represented by any one of the following formulas C-1 to C-8, a compound:

In the formulas C-1 to C-8,
* means the part where the bond is formed;
n is an integer from 0 to 4;
o is an integer from 0 to 3;
R ₁₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, 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 , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha Nyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group is selected from the group, or combined with an adjacent group to form a condensed ring, and wherein R ₁₁ is a plurality of these are the same or different from each other;
An _alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, The arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ of arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ of an aryl boron group, a C ₆ ~ C ₆₀ aryl phosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylsilyl group substituted with one or more substituents selected from the group, or When unsubstituted and 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 a C ₁ ~ C ₃₀ Alkyl group, C ₆ ~ C ₃₀ A compound selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms. According to claim 1,
The compound is a compound characterized in that it is selected from the group consisting of:

An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device comprising a compound represented by the formula (1) of claim 1. 14. The method of claim 13,
The organic material layer is an organic electroluminescent device comprising one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer.

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