KR102656918B1 - 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 containing the same. The compound according to the present invention is used in an organic material layer, preferably an electron transport layer, of an organic electroluminescent device, thereby increasing the luminous efficiency, driving voltage, and Lifespan can be improved.

Description

Organic compounds and organic electroluminescent devices containing the same {ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE 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 containing the same.

Beginning with the observation of organic thin film luminescence by Bernanose in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and Tang in 1987. ) presented an organic electroluminescent device with a layered structure divided into a functional layer of a hole layer and a light-emitting layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.

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

Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.

Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.

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

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However, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and thermal stability is very poor, so they are not at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

In order to solve the above problems, the purpose of the present invention is to provide a new compound that can improve the efficiency, lifespan, and stability of an organic electroluminescent device and an organic electroluminescent device using the compound.

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

[Formula 1]

In Formula 1,

X ₁ and X ₂ are each independently N or C(R ₅ ), but at least one of X ₁ and X ₂ is N;

m and n are each independently integers from 0 to 5;

R ₁ and R ₂ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when each of R ₁ and R ₂ is plural, they are the same or different from each other and;

L ₁ to L ₃ are each independently selected from the group consisting of a single bond, a C ₆ to C ₃₀ arylene group, and a heteroarylene group having 5 to 30 nuclear atoms;

R ₃ to R ₅ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 ~ selected from the group consisting of a C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group;

The arylene group and heteroarylene group of L ₁ to L ₃ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R ₁ to R ₅ , arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine 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 with 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 with 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 arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and C ₆ ~ C ₆₀ is substituted or unsubstituted with one or more substituents selected from the group consisting of arylsilyl groups, and when substituted with a plurality of substituents, these may be the same or different from each other;

At least one of R ₃ and R ₄ is selected from the substituents represented by Formula 2 or 3 below;

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

* refers to the part where the combination takes place;

X ₁ to X ₁₀ are each independently N or C(R ₆ ), but at least one of X ₁ to X ₁₀ is N;

R ₆ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , 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 arylphosphine group , is selected from the group consisting of a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, and when there is a plurality of R ₆ , they are the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group _, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphine 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 with 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 with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. And when substituted with a plurality of substituents, these may be the same or different from each other.

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

In the present invention, “alkyl” is a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl. etc., but is not limited to this.

In the present invention, “alkenyl” 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 double bond, examples of which include vinyl, Examples include allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

In the present invention, “alkynyl” 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 of which include ethynyl. , 2-propynyl, etc., but is not limited thereto.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is replaced with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and it is further interpreted to include a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; Examples include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

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

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

In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms.

“Cycloalkyl” in the present invention refers to 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, and adamantine.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon, preferably 1 to 3 carbons in the ring, 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 and piperazine.

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 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

The compound represented by Formula 1 according to the present invention has excellent thermal stability, hole transport, hole injection performance, electron transport and electron injection performance, and has fast electron mobility, so it can be used as an organic layer material, preferably a light-emitting layer material, of an organic electroluminescent device. , can be used as a hole injection layer, hole transport layer, electron injection layer, and electron transport layer.

The novel compound represented by Formula 1 of the present invention is an organic compound that has superior luminescence performance, low driving voltage, high efficiency, and long lifespan compared to conventional materials when used as a light-emitting layer material, hole injection layer, hole transport layer, electron injection layer, and electron transport layer. Electroluminescent devices can be manufactured, and full-color display panels with greatly improved performance and lifespan can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. Novel organic compounds

The new organic compound according to the present invention has a structure in which an aryl group and a heteroaryl group are bonded to a Y-shaped basic skeleton centered on pyrimidine or triazine. In the present invention, by changing the position and number of hetero atoms in the basic skeleton described above, an electron attractor (EWG) with high electron absorption, such as phenanthridine, benzonaphthyridine, pyridoquinoxaline, etc., is bonded to the entire molecule. Electron mobility can be increased. Specifically, the novel compound of the present invention is characterized as a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

X ₁ and X ₂ are each independently N or C(R ₅ ), but at least one of X ₁ and X ₂ is N;

m and n are each independently integers from 0 to 5;

R ₁ and R ₂ 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 Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when each of R ₁ and R ₂ is plural, they are the same or different from each other and;

L ₁ to L ₃ are each independently selected from the group consisting of a single bond, a C ₆ to C ₃₀ arylene group, and a heteroarylene group having 5 to 30 nuclear atoms;

R ₃ to R ₅ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 ~ selected from the group consisting of a C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group;

The arylene group and heteroarylene group of L ₁ to L ₃ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group of R ₁ to R ₅ , arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine 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 with 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 with 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 arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and C ₆ ~ C ₆₀ is substituted or unsubstituted with one or more substituents selected from the group consisting of arylsilyl groups, and when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, it is preferable in terms of luminous efficiency that at least one of R ₃ and R ₄ is a substituent represented by the following Formula 2 or Formula 3, but is not limited thereto:

[Formula 2]

[Formula 3]

In Formula 2 and Formula 3,

* refers to the part where the combination takes place;

X ₁ to X ₁₀ are each independently N or C(R ₆ ), but at least one of X ₁ to X ₁₀ is N;

R ₆ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, Heteroaryl group with 5 to 60 nuclear atoms, aryloxy group with C ₆ to C ₆₀ , alkyloxy group with C ₁ to C ₄₀ , cycloalkyl group with C ₃ to C ₄₀ , heterocycloalkyl group with 3 to 40 nuclear atoms. , C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ mono or diarylphosphinyl group and C ₆ ~ C ₆₀ arylsilyl group, or in combination with an adjacent group (for example, L ₂ and other adjacent R ₆ , etc.) may form a condensed ring, and when R ₆ is plural, they are the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group _, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphine 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 with 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 with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. And when substituted with a plurality of substituents, these may be the same or different from each other.

The compound of the present invention can have fast electron mobility by changing the number and position of nitrogen in the basic skeleton of the phenanthrene substituent. As a result, the efficiency of the organic electroluminescent device can be increased by increasing the performance of the electron transport layer. In addition, the light-emitting layer contributes to an increase in the number of excitons, which can improve the luminous efficiency of the device, and improve the durability and stability of the device, effectively increasing the lifespan of the device.

According to a preferred embodiment of the present invention, the substituent represented by Formula 2 may be a substituent represented by any one of the following Formulas A-1 to A-11:

In the above formulas A-1 to A-11,

p is an integer from 0 to 4;

q is an integer from 0 to 3;

r and s are each independently integers from 0 to 2;

R ₇ and R ₈ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ Aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylsilyl group, or an adjacent group (for example, L ₂ , another adjacent R ₇ or R ₈ , etc.) may be combined to form a condensed ring, and when each of R ₇ and R ₈ is plural, they are the same or different from each other;

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, aryl group of R ₇ and R ₈ Boron group, arylphosphine 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 with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ Arylamine group of C ₆₀ , cycloalkyl group of C ₃ ~ C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, alkylsilyl group of C ₁ ~ C ₄₀ , alkyl boron group of C ₁ ~ C ₄₀ , C ₆ ~ Substituted with one or more substituents selected from the group consisting of C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When unsubstituted or substituted with a plurality of substituents, they may be the same or different from each other,

* and R ₆ are as defined in Formula 2 above.

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-6:

In the above formulas B-1 to B-6,

* refers to the part where the combination takes place;

p and l are each independently an integer from 0 to 4;

q and t are each independently integers from 0 to 3;

s is an integer from 0 to 2;

R ₇ and R ₈ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ Aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylsilyl group, or an adjacent group (for example, L ₂ , another adjacent R ₇ or R ₈ , etc.) may be combined to form a condensed ring, and when each of R ₇ and R ₃ is plural, they are the same or different from each other;

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, aryl group of R ₇ and R ₈ Boron group, arylphosphine 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 with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ Arylamine group of C ₆₀ , cycloalkyl group of C ₃ ~ C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, alkylsilyl group of C ₁ ~ C ₄₀ , alkyl boron group of C ₁ ~ C ₄₀ , C ₆ ~ Substituted with one or more substituents selected from the group consisting of C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, L ₁ to L ₃ may each independently be a single bond or a C ₆ to C ₁₈ arylene group.

According to a preferred embodiment of the present invention, L ₁ to L ₃ may each independently be selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, and an anthracenyl group.

According to a preferred embodiment of the present invention, R ₃ is a C ₁ ~ C ₄₀ alkyl group, a C ₂ ~ C ₄₀ alkenyl group, a C ₂ ~ C ₄₀ alkynyl group, a C ₆ ~ C ₆₀ aryl group, or a nucleus. It may be a heteroaryl group having 5 to 60 atoms.

According to a preferred embodiment of the present invention, R ₃ is methyl, propyl, butyl, phenyl, biphenyl, naphthalenyl, anthracenyl, phenanthrenyl, pyrenyl, triphenylenyl, fluorenyl, spy. It may be selected from the group consisting of lobifluorenyl group and benzofluorenyl group.

본 발명에서 상기 화학식 1로 표시되는 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.The compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

In the present invention, the compound represented by Formula 1 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 synthesis examples described later.

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2. Organic electric field light emitting element

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) containing the compound represented by Formula 1 according to the above-described 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 It includes a compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially stacked. At this time, an electron transport auxiliary layer may be additionally laminated between the light emitting layer and the electron transport layer, and an electron injection layer may be additionally laminated on the electron transport layer. In the present invention, one or more of the hole injection layer, hole transport layer, light emitting layer, light emission auxiliary layer, lifespan improvement layer, electron transport layer, electron transport auxiliary layer, and electron injection layer may include the compound represented by Formula 1.

The compound represented by Formula 1 of the present invention has an electron withdrawing group (EWG) with high electron absorption, such as an aryl group and a heteroaryl group, bonded to a Y-shaped basic skeleton centered on a triazine, thereby increasing the electron mobility of the entire molecule. You can. That is, the compound represented by Formula 1 of the present invention has high electron mobility, so it can increase the performance of the electron transport layer and increase the efficiency of the organic electroluminescent device when used as a material for the electron transport layer or electron transport auxiliary layer. In addition, the emission efficiency can be improved by contributing to an increase in the number of excitons in the light-emitting layer, and the durability and stability of the device are improved, so the lifespan of the device can also be efficiently increased.

In addition, the structure of the organic electroluminescent device of the present invention may be one in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or adhesive layer is inserted at the interface between the electrode and the organic material layer.

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

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

There is no particular limitation on the substrate that can be used in the present invention, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.

In addition, the anode material includes 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); 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 are not limited thereto.

Additionally, the cathode material includes metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO ₂ /Al, etc., but are not limited thereto.

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

[ Preparation example 1] 2-(3,5- Dibromophenyl )-4,6-diphenyl-1,3,5-triazine synthesis

2-Chloro-4,6-diphenyl-1,3,5-triazine (100 g, 373.5 mmol) and (3,5-dibromophenyl)boronic acid (104.5 g, 373.5 mmol) and Pd(PPh) ₃ ) ₄ (21.6 g, 18.6 mmol) and K ₂ CO ₃ (103.3 g, 747.0 mmol) were added to 1000 ml of toluene, 200 ml of EtOH, and 200 ml of H ₂ O and heated to reflux for 2 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine (104.7 g, yield) 60%) was obtained.

¹ H-NMR: δ 7.40-7.41 (m, 4H), 7.51 (m, 4H), 7.96 (s, 1H), 8.27-8.28 (m, 4H)

[LCMS]: 467

[ Preparation example 2] 6-(3- bromo -5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) of phenanthridine synthesis

<Step 1> 6-(4,4,5,5- tetramethyl -1,3,2- Dioxaborolan -2 days) of phenanthridine synthesis

6-bromophenanthridine (15.4 g, 59.6 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2 -Dioxabororane) (18.0 g, 70.8 mmol), Pd(dppf)Cl ₂ (2.4 g, 3.0 mmol), and KOAc (11.6 g, 118.8 mmol) were added to 300ml of 1,4-dioxane and incubated for 12 hours. It was heated and refluxed. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenanthridine, was purified using column chromatography. (5.4 g, yield 30%) was obtained.

¹ H-NMR: δ 1.24 (s, 12H), 7.41-7.42 (m, 1H), 7.48-7.49 (m, 1H), 7.59-7.60 (m, 1H), 7.76-7.78 (m, 2H), 7.92 (d, 1H), 7.98 (d, 1H), 8.06(d, 1H)

[LCMS]: 305

<Step 2> 6-(3- bromo -5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) of phenanthridine synthesis

2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine (7.6 g, 16.3 mmol) synthesized in Preparation Example 1 and 6-(4 synthesized above ,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenanthridine (5.0 g, 16.3 mmol) and Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol) , K ₂ CO ₃ (4.5 g, 32.6 mmol) was added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) was purified using column chromatography. Phenanthridine (6.4 g, yield 70%) was obtained.

¹ H-NMR: δ 7.41-7.42 (m, 3H), 7.48-7.49 (m, 2H), 7.50-7.51 (m, 4H), 7.59-7.60 (m, 1H), 7.76-7.78 (m, 2H) , 7.92-7.93 (m, 2H), 7.98 (d, 1H), 8.06 (s, 1H), 8.15 (s, 1H), 8.27-8.28 (m, 4H)

[LCMS] : 565

[ Preparation example 3] 5- (3-Bromo-5- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) Benzo[c][2,7]naphthyridine synthesis

<Step 1> Synthesis of 5-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)benzo[c][2,7]naphthyridine

5-Bromobenzo[c][2,7]naphthyridine (15.4 g, 59.6 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2' -Bi(1,3,2-dioxabororane) (18.0 g, 70.8 mmol) and Pd(dppf)Cl ₂ (2.4 g, 3.0 mmol) and KOAc (11.6 g, 118.8 mmol) were added to 1,4- It was added to 300ml of dioxane and heated to reflux for 12 hours. After completion of the reaction, it was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, the target compound, 5-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)benzo[c ][2,7]naphthyridine (5.6 g, yield 35%) was obtained.

¹ H-NMR: δ 1.24 (s, 12H), 7.38 (d, 1H), 7.60 (t, 1H), 7.78 (t, 1H), 7.96 (d, 1H), 8.06 (d, 1H), 8.43 ( d, 1H), 9.51 (s, 1H)

[LCMS]: 306

<Step 2> 5- (3-Bromo-5- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) Benzo[c][2,7]naphthyridine synthesis

2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine (7.6 g, 16.3 mmol) synthesized in Preparation Example 1 and 5-(4 synthesized above ,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)benzo[c][2,7]naphthyridine (5.0 g, 16.3 mmol) and Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol) and K ₂ CO ₃ (4.5 g, 32.6 mmol) were added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 5-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) was purified using column chromatography. Benzo[c][2,7]naphthyridine (6.0 g, yield 65%) was obtained.

¹ H-NMR: δ 7.38 (d, 1H), 7.41-7.42 (m, 2H), 7.48 (s, 1H), 7.50-7.51 (m, 4H), 7.60-7.61 (m, 1H), 7.78 (t , 1H), 7.93 (s, 1H), 7.98 (d, 1H), 8.08 (d, 1H), 8.15 (s, 1H), 8.27-8.28 (m, 4H), 8.43 (d, 1H), 9.34 ( s, 1H)

[LCMS] : 566

[ Preparation example 4] 6- (3-Bromo-5- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) Pyrido[3,2-f]quinoxaline synthesis

<Step 1> Synthesis of 6-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)pyrido[3,2-f]quinoxaline

6-Bromopyrido[3,2-f]quinoxaline (15.4 g, 59.6 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'- B(1,3,2-dioxabororane) (18.0 g, 70.8 mmol) and Pd(dppf)Cl ₂ (2.4 g, 3.0 mmol) and KOAc (11.6 g, 118.8 mmol) were reacted with 1,4-dioxabororane (18.0 g, 70.8 mmol). It was added to 300ml of oxalic acid and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrido [ 3,2-f]quinoxaline (8.8 g, yield 49%) was obtained.

¹ H-NMR: δ 1.24 (s, 12H), 7.58 (t, 1H), 8.06 (d, 1H), 8.38 (d, 1H), 8.70 (s, 2H), 8.83 (d, 1H)

[LCMS] : 307

<Step 2> 6- (3-Bromo-5- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) Pyrido[3,2-f]quinoxaline synthesis

2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine (7.6 g, 16.3 mmol) synthesized in Preparation Example 1 and 6-(4 synthesized above ,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)pyrido[3,2-f]quinoxaline (5.0 g, 16.3 mmol) and Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol) and K ₂ CO ₃ (4.5 g, 32.6 mmol) were added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) was purified using column chromatography. Pyrido[3,2-f]quinoxaline (5.5 g, yield 60%) was obtained.

¹ H-NMR: δ 7.41-7.42 (m, 4H), 7.50-7.51 (m, 4H), 7.58 (t, 1H), 7.64 (s, 1H), 8.28-8.29 (m, 5H), 8.38 (d) , 1H), 8.74 (s, 2H), 8.83 (d, 1H)

[LCMS]: 567

[ Preparation example 5] 6- (3-Bromo-5- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) of pyrido[4,3-c][1,5]naphthyridine. synthesis

<Step 1> 6-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)pyrido[4,3-c][1,5]naphthyridine synthesis of

6-Bromopyrido[4,3-c][1,5]naphthyridine (15.4 g, 59.6 mmol) and 4,4,4',4',5,5,5',5'-octamethyl- 2,2'-bi(1,3,2-dioxabororane) (18.0 g, 70.8 mmol) and Pd(dppf)Cl ₂ (2.4 g, 3.0 mmol), KOAc (11.6 g, 118.8 mmol) It was added to 300ml of 1,4-dioxane and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrido [ 4,3-c][1,5]naphthyridine (5.4 g, yield 30%) was obtained.

¹ H-NMR: δ 1.24 (s, 12H), 7.78 (d, 1H), 7.91 (t, 1H), 8.50 (d, 1H), 8.75 (d, 1H), 9.10 (d, 1H), 9.39 ( s, 1H)

[LCMS] : 307

<Step 2> 6- (3-Bromo-5- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) of pyrido[4,3-c][1,5]naphthyridine. synthesis

2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine (7.6 g, 16.3 mmol) synthesized in Preparation Example 1 and 6-(4 synthesized above ,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)pyrido[4,3-c][1,5]naphthyridine (5.0 g, 16.3 mmol) and Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol) and K ₂ CO ₃ (4.5 g, 32.6 mmol) were added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) was purified using column chromatography. Pyrido[4,3-c][1,5]naphthyridine (5.5 g, yield 60%) was obtained.

¹ H-NMR: δ 7.41-7.42 (m, 2H), 7.48 (s, 1H), 7.50-7.51 (m, 4H), 7.78 (d, 1H), 7.91-7.93 (m, 2H), 8.15 (s) , 1H), 8.27-8.28 (m, 4H), 8.50 (s, 1H), 8.75 (d, 1H), 9.10 (d, 1H), 9.39 (s, 1H)

[LCMS]: 567

[ Preparation example 6] 4-(3- bromo Synthesis of -5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline

<Step 1> 4-(4,4,5,5- tetramethyl -1,3,2- Dioxaborolan -2-day) Synthesis of -1,10-phenanthroline

4-Bromo-1,10-phenanthroline (15.4 g, 59.6 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi( 1,3,2-dioxabororane) (18.0 g, 70.8 mmol), Pd(dppf)Cl ₂ (2.4 g, 3.0 mmol), and KOAc (11.6 g, 118.8 mmol) were added to 300ml of 1,4-dioxane. and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 4-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)-1, 10-phenanthroline (8.6 g, yield 49%) was obtained.

¹ H-NMR: δ 1.24 (s, 12H), 7.48 (d, 1H), 7.58 (t, 1H), 7.81 (d, 1H), 8.06 (d, 1H), 8.38(d, 1H), 8.83( d, 2H)

[LCMS]: 306

<Step 2> 4-(3- bromo Synthesis of -5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline

2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine (7.6 g, 16.3 mmol) synthesized in Preparation Example 1 and 4-(4 synthesized above ,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline (5.0 g, 16.3 mmol) and Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol), K ₂ CO ₃ (4.5 g, 32.6 mmol) were added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 4-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) was purified using column chromatography. -1,10-phenanthroline (6.0 g, yield 65%) was obtained.

¹ H-NMR: δ 7.41-7.42 (m, 4H), 7.48 (d, 1H), 7.50-7.51 (m, 4H), 7.58 (t, 1H), 7.64 (s, 1H), 7.81 (d, 1H) ), 8.06 (d, 1H), 8.27-8.28 (m, 4H), 8.38 (d, 1H), 8.83 (d, 1H), 8.89 (d, 1H)

[LCMS] : 566

[ Synthesis example 1] Synthesis of Compound 1

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)phenanthridine (5 g, 8.8 mmol) and phenyl boro of Preparation Example 2 Ninic acid (1.2 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), and K ₂ CO ₃ (2.4 g, 17.6 mmol) were added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O for 12 hours. It was heated and refluxed. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'- Biphenyl]-3-yl)phenanthridine (3.4 g, yield 70%) was obtained.

[LCMS] : 562

[ Synthesis example 2] Synthesis of compound 8

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)phenanthridine (5 g, 8.8 mmol) of Preparation Example 2 and naphthalene- 2-ylboronic acid (1.7 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), and K ₂ CO ₃ (2.4 g, 17.6 mmol) were added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O. It was added and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(naphthalene-2, was purified using column chromatography. -yl)phenyl)phenanthridine (3.9 g, yield 73%) was obtained.

[LCMS] : 612

[ Synthesis example 3] Synthesis of Compound 17

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)phenanthridine (5 g, 8.8 mmol) and (9) of Preparation Example 2 ,9-dimethyl-9H-fluoren-2-yl)boronic acid (2.3 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) It was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-(9,9-dimethyl-9H-fluoren-2-yl)-5-(4,6-diphenyl-1, was purified using column chromatography. , 3,5-triazin-2-yl) phenyl) phenanthridine (4.2 g, yield 71%) was obtained.

[LCMS] : 678

[ Synthesis example 4] Synthesis of compound 29

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)phenanthridine (5 g, 8.8 mmol) and (9) of Preparation Example 2 ,9-diphenyl-9H-fluoren-4-yl)boronic acid (3.5 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(9,9) was purified using column chromatography. -Diphenyl-9H-fluoren-4-yl)phenyl)phenanthridine (4.6 g, yield 65%) was obtained.

[LCMS] : 802

[ Synthesis example 5] Synthesis of compound 89

5-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)benzo[c][2,7]naphthyridine (5) of Preparation Example 3 g, 8.8 mmol), phenylboronic acid (1.2 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) in 200 ml of toluene, 40 ml of EtOH, H ₂ O was added to 40ml and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 5-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'- Biphenyl]-3-yl)benzo[c][2,7]naphthyridine (3.4 g, yield 70%) was obtained.

[LCMS] : 563

[ Synthesis example 6] Synthesis of compound 96

5-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)benzo[c][2,7]naphthyridine (5) of Preparation Example 3 g, 8.8 mmol), naphthalene-2-ylboronic acid (1.7 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) in 200 ml of toluene, It was added to 40ml of EtOH and 40ml of H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(naphthalene-2, was purified using column chromatography. -yl)phenyl)benzo[c][2,7]naphthyridine (3.9 g, yield 73%) was obtained.

[LCMS] : 613

[ Synthesis example 7] Synthesis of Compound 105

5-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)benzo[c][2,7]naphthyridine (5) of Preparation Example 3 g, 8.8 mmol) and (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (2.3 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 5-(3-(9,9-dimethyl-9H-fluoren-2-yl)-5-(4,6-diphenyl-1, was purified using column chromatography. ,3,5-triazin-2-yl)phenyl)benzo[c][2,7]naphthyridine (4.2 g, yield 71%) was obtained.

[LCMS] : 679

[ Synthesis example 8] Synthesis of compound 117

5-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)benzo[c][2,7]naphthyridine (5) of Preparation Example 3 g, 8.8 mmol) and (9,9-diphenyl-9H-fluoren-4-yl)boronic acid (3.5 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(9,9) was purified using column chromatography. -Diphenyl-9H-fluoren-4-yl)phenyl)benzo[c][2,7]naphthyridine (4.6 g, yield 65%) was obtained.

[LCMS] : 803

[ Synthesis example 9] Synthesis of compound 177

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyrido[3,2-f]quinoxaline (5) of Preparation Example 4 g, 8.8 mmol), phenylboronic acid (1.2 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) in 200 ml of toluene, 40 ml of EtOH, H ₂ O was added to 40ml and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'- Biphenyl]-3-yl)pyrido[3,2-f]quinoxaline (3.4 g, yield 70%) was obtained.

[LCMS] : 564

[ Synthesis example 10] Synthesis of compound 184

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyrido[3,2-f]quinoxaline (5) of Preparation Example 4 g, 8.8 mmol), naphthalene-2-ylboronic acid (1.7 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) in 200 ml of toluene, It was added to 40ml of EtOH and 40ml of H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(naphthalene-2, was purified using column chromatography. -yl)phenyl)pyrido[3,2-f]quinoxaline (3.9 g, yield 73%) was obtained.

[LCMS] : 614

[ Synthesis example 11] Synthesis of compound 193

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyrido[3,2-f]quinoxaline (5) of Preparation Example 4 g, 8.8 mmol) and (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (2.3 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, it was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-(9,9-dimethyl-9H-fluoren-2-yl)-5-(4,6-diphenyl-1, was purified using column chromatography. , 3,5-triazin-2-yl) phenyl) pyrido [3,2-f] quinoxaline (4.2 g, yield 71%) was obtained.

[LCMS] : 680

[ Synthesis example 12] Synthesis of compound 195

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyrido[3,2-f]quinoxaline (5) of Preparation Example 4 g, 8.8 mmol) and (9,9-diphenyl-9H-fluoren-2-yl)boronic acid and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) ) was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(9,9) was purified using column chromatography. -Diphenyl-9H-fluoren-2-yl)phenyl)pyrido[3,2-f]quinoxaline (4.6 g, yield 65%) was obtained.

[LCMS]: 804

[ Synthesis example 13] Synthesis of compound 209

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyrido[4,3-c][1,5 of Preparation Example 5 ]Naphthyridine (5 g, 8.8 mmol), phenylboronic acid (1.2 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), and K ₂ CO ₃ (2.4 g, 17.6 mmol) were dissolved in 200 ml of toluene. , 40ml of EtOH and 40ml of H ₂ O were added and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'- Biphenyl]-3-yl)pyrido[4,3-c][1,5]naphthyridine (3.4 g, yield 70%) was obtained.

[LCMS] : 564

[ Synthesis example 14] Synthesis of compound 213

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyrido[4,3-c][1,5 of Preparation Example 5 ]naphthyridine (5 g, 8.8 mmol) and [1,1'-biphenyl]-4-ylboronic acid (1.9 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) was added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1': 4',1''-terphenyl]-3-yl)pyrido[4,3-c][1,5]naphthyridine (2.8 g, yield 50%) was obtained.

[LCMS] : 640

[ Synthesis example 15] Synthesis of compound 214

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyrido[4,3-c][1,5 of Preparation Example 5 ]naphthyridine (5 g, 8.8 mmol) and [1,1'-biphenyl]-3-ylboronic acid (1.9 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) was added to 200 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1': 3',1''-terphenyl]-3-yl)pyrido[4,3-c][1,5]naphthyridine (2.8 g, yield 50%) was obtained.

[LCMS] : 640

[ Synthesis example 16] Synthesis of compound 216

6-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyrido[4,3-c][1,5 of Preparation Example 5 ]naphthyridine (5 g, 8.8 mmol), naphthalene-2-ylboronic acid (1.7 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) ) was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 12 hours. After completion of the reaction, it was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(naphthalene-2, was purified using column chromatography. -yl)phenyl)pyrido[4,3-c][1,5]naphthyridine (3.9 g, yield 73%) was obtained.

[LCMS] : 614

[ Synthesis example 17] Synthesis of compound 225

4-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline of Preparation Example 6 (5 g, 8.8 mmol), phenylboronic acid (1.2 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) in 200 ml of toluene, 40 ml of EtOH, 40 ml of H ₂ O. and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 4-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'- Biphenyl]-3-yl)-1,10-phenanthroline (3.4 g, yield 370%) was obtained.

[LCMS] : 563

[ Synthesis example 18] Synthesis of compound 226

4-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline of Preparation Example 6 (5 g, 8.8 mmol) and naphthalene-2-ylboronic acid (1.7 g, 9.7 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), and K ₂ CO ₃ (2.4 g, 17.6 mmol) were dissolved in 200 ml of toluene, 40 ml of EtOH, It was added to 40ml of H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(naphthalene-2, was purified using column chromatography. -yl)phenyl)-1,10-phenanthroline (3.9 g, yield 73%) was obtained.

[LCMS] : 613

[ Synthesis example 19] Synthesis of compound 227

4-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline of Preparation Example 6 (5 g, 8.8 mmol) and (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (2.3 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g , 17.6 mmol) was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 4-(3-(9,9-dimethyl-9H-fluoren-2-yl)-5-(4,6-diphenyl-1, was purified using column chromatography. ,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline (4.2 g, yield 71%) was obtained.

[LCMS] : 679

[ Synthesis example 20] Synthesis of compound 228

4-(3-bromo-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline of Preparation Example 6 (5 g, 8.8 mmol) and (9,9-diphenyl-9H-fluoren-4-yl)boronic acid (3.5 g, 9.7 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (2.4 g, 17.6 mmol) was added to 200ml of toluene, 40ml of EtOH, and 40ml of H ₂ O, and heated to reflux for 12 hours. After completion of the reaction, it was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, the target compound, 4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(9,9) was purified using column chromatography. -Diphenyl-9H-fluoren-4-yl)phenyl)-1,10-phenanthroline (4.6 g, yield 65%) was obtained.

[LCMS] : 803

[ Example 1 to 20] Blue Organic electric field Fabrication of light emitting devices

Compounds 1, 8, 17, 29, 89, 96, 105, 117, 177, 184, 193, 195, 209, 213, 214, 216, 225, 226, 227, and 228 synthesized in the synthesis examples are commonly known methods. After high-purity sublimation purification, a blue organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with a 1500 Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics Co., Ltd., 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30nm)/Compound 1, 8, 17, 29 , 89, 96, 105, 117, 177, 184, 193, 195, 209, 213, 214, 216, 225, 226, 227, 228 each compound (30 nm)/LiF (1 nm)/Al (200 nm) ) to produce an organic electroluminescent device.

[ Comparative example 1] Blue Organic electric field Fabrication of light emitting devices

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

[ Comparative example 2] Blue Organic electric field Fabrication of light emitting devices

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

The structures of NPB, AND, and Alq3 used in Examples 1 to 20 and Comparative Examples 1 and 2 are as follows.

[ Evaluation example One]

For each blue organic electroluminescent device manufactured in Examples 1 to 20 and Comparative Examples 1 and 2, the driving voltage, current efficiency, and luminescence peak at a current density (10) mA/cm2 were measured, and the results are shown in the table below. It is shown in 1.

Sample electron transport layer driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 1 One 4.5 458 7.0 Example 2 8 4.6 459 7.1 Example 3 17 4.1 458 7.1 Example 4 29 4.0 455 6.8 Example 5 89 4.3 456 6.7 Example 6 96 4.4 457 6.7 Example 7 105 3.9 456 6.9 Example 8 117 3.8 452 7.1 Example 9 177 4.0 448 7.3 Example 10 184 4.1 460 7.3 Example 11 193 3.6 468 6.8 Example 12 195 3.5 465 6.9 Example 13 209 3.9 457 6.8 Example 14 213 4.1 456 6.4 Example 15 214 4.1 455 6.5 Example 16 216 4.2 459 6.5 Example 17 225 4.1 461 6.9 Example 18 226 3.9 464 7.1 Example 19 227 3.6 467 7.1 Example 20 228 3.9 467 6.7 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 1, the blue organic electroluminescent device using the compound of the present invention in the electron transport layer (Examples 1 to 20) is the same as the blue organic electroluminescent device using the conventional Alq ₃ in the electron transport layer (Comparative Example 1) and It was found that it exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device without an electron transport layer (Comparative Example 2).

Claims (10)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
X ₁ and X ₂ are both N;
m and n are 0;
R ₁ and R ₂ are hydrogen;
L ₁ and L ₂ are each independently selected from the group consisting of a single bond and an arylene group of C ₆ to C ₁₂ , but at least one of L ₁ and L ₂ is a single bond,
L ₃ is selected from the group consisting of a single bond and a C ₆ to C ₁₂ arylene group;
One of R ₃ and R ₄ is an aryl group of C ₆ to C ₆₀ , and the other is an aryl group of the following formulas A-3, A-4, A-6 to A-11, B-2 and B-4 to B- It is a substituent selected from the group consisting of 6;


In the formulas A-3, A-4, A-6 to A-11, B-2 and B-4 to B-6,
* refers to the part where the combination takes place;
p and l are each independently an integer from 0 to 4;
q and t are each independently integers from 0 to 3;
R ₆ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , 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 arylphosphine group , is selected from the group consisting of a C ₆ ~ C ₆₀ mono or diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, and when there is a plurality of R ₆ , they are the same or different from each other;
R ₇ and R ₈ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ Aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ may be selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring, and R ₇ and R ₈ when each is plural, they are the same or different from each other;
The arylene group of L ₁ to L ₃ , the alkyl group of R ₆ to 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. , alkyl silyl group, alkyl boron group, aryl boron group, aryl phosphine group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 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 with 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 arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. is substituted or unsubstituted with one or more substituents selected from the group consisting of, and when substituted with a plurality of substituents, they may be the same or different from each other,
The aryl group of any one of R ₃ and R ₄ of C ₆ to C ₆₀ is each independently selected from an alkyl group of C ₁ to C ₄₀ , an alkenyl group of C ₂ to C ₄₀ , an alkynyl group of C ₂ to C 40, and a C ₆ to C ₄₀ alkyl group. C ₆₀ It is substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups, and when substituted with a plurality of substituents, these may be the same or different from each other. delete delete delete According to paragraph 1,
A compound wherein L ₁ to L ₃ are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, and a naphthalenyl group. delete delete According to paragraph 1,
The compound represented by Formula 1 is characterized in that it is selected from the group consisting of the following compounds:

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,
An organic electroluminescent device, wherein at least one of the one or more organic layers includes the compound represented by the formula (1) of claim 1. According to clause 9,
The organic material layer containing the compound is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a lifespan improvement layer, a light emitting layer, and a light emitting auxiliary layer.