KR102263844B1 - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel perimidine-based compound having excellent hole injection and transport ability, light emitting ability, and the like, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic material layers.

Description

Organic light emitting compound and organic electroluminescent device using same {ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel perimidine-based compound having excellent hole injection and transport ability and light emitting ability, and luminous efficiency by including the same in one or more organic material layers , It relates to an organic electroluminescent device with improved characteristics such as driving voltage and lifespan.

The study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices'), which led to blue electroluminescence using anthracene single crystals in 1965, started with Bernanose's observation of organic thin film emission in the 1950s. In 1987, an organic EL device having a stacked structure divided into a hole layer and a functional layer of a light emitting layer was proposed by Tang. Since then, in order to make a high-efficiency, long-life organic EL 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.

When a voltage is applied between the two electrodes of the organic electroluminescent device, holes are injected from the anode, and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall 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 material for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the emission color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better natural colors. 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. The development of such a phosphorescent material can theoretically improve luminous efficiency up to four times compared to fluorescence, and thus, attention is focused on phosphorescent host materials as well as phosphorescent dopants.

To date, the hole injection layer, the hole transport layer. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq _3, etc. represented by the following chemical formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant/host materials as light emitting materials. In particular, among the light emitting materials, as a phosphorescent material having a great advantage in terms of efficiency improvement _{, a metal complex compound containing Ir such as Firpic, Ir(ppy) 3} , (acac)Ir(btp) _{2 ,} etc. is used as a blue, green, and red dopant material. is being used So far, CBP has shown excellent properties as a phosphorescent host material.

However, although the existing materials have advantages in terms of light emitting properties, they are not satisfactory in terms of lifespan in organic EL devices due to their low glass transition temperature and very poor thermal stability.

Republic of Korea Patent Publication 2011-0066763

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 excellent in all of the hole injection and transport layer, the light emitting layer, and the like.

Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage and high luminous efficiency and having an improved lifespan, including the novel organic 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 is C(R), or N;

R and R _{1 To} R ₇ are the same as or different from each other, and 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 of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ 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 of an aryl boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group selected from the group consisting of,

Ar ₁ is a 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, C ₆ ~ C ₆₀ Aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ 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 Arylphosphine group, C ₆ ~ C ₆₀ Mono or diarylphosphine group It is selected from the group consisting of a pinyl group and a C ₆ ~ C _{60 arylamine group,}

R and R ₁ , R and R ₂ , R ₁ and Ar ₁ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ and R ₇ and Ar _One of 1 may combine with each other to form a condensed heteroaromatic ring including at least one of N, O, S, and Si, or a condensed aromatic ring.

The Ar ₁ , R And R _{1 To} R ₇ Alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron Group, arylphosphine group, mono or diarylphosphinyl group and arylamine group are each independently, 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 of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 ~ aryl phosphonium pingi of C _60, which may be substituted with at least one member selected from the group consisting of C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl amine. When substituted with a plurality of substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ may be a substituent represented by the following formula (2) or a phenyl group.

[Formula 2]

In Formula 2,

* means a moiety bonded to Formula 1;

L is a single bond, or _{is selected from the group consisting of a C 6} ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, preferably a single bond, or a phenylene group or a biphenylene group; Y _{1 To} Y _{5 Are} the same as or different from each other, and each independently is N or C(R ₈ ), provided _{that at least one of Y 1 To} Y ₅ is N, and when R ₈ is plural, they are the same or different from each other, ;

R ₈ 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 ₆ ~ C ₄₀ aryl group, Heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ Aryloxy group C ₁ ~ C ₄₀ Alkyloxy group, C ₃ ~ C ₄₀ Cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ Mono or diarylphosphinyl group and C ₆ ~ C _{40 It} is selected from the group consisting of an arylsilyl group, or is _{combined with an adjacent group (eg, L, another adjacent R 8} ) to form a condensed ring can form;

Alkyl group of the R _8, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl 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 of alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ 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 ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ unsubstituted and, when the substituents are plural, they may be the same as or different from each other.

In addition, according to a preferred embodiment of the present invention, in the compound represented by Formula 1, Ar ₁ may be a substituent selected from the group consisting of substituents represented by A-1 to A-15 below:

In the above A-1 to A-15,

L and R ₈ are each as defined in Formula 2 above,

n is an integer of 0 to 4, and when n is 0, _{it means that hydrogen is not substituted with a substituent R 9} , and when n is an integer of 1 to 4, R ₉ is 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 ~ C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C _{40 60} aryloxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ mono or diaryl phosphine of C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ P It is selected from the group consisting of a nyl group and a C ₆ ~ C _{40 arylsilyl group, or may be combined with an adjacent group (eg, L, R 8} or other R _9, etc.) to form a condensed ring,

Alkyl group of the R _9, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an 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 of alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ 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 ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ unsubstituted and, when the substituents are plural, they may be the same as or different from each other.

In addition, the present invention provides 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, wherein at least one of the one or more organic material layers One provides an organic electroluminescent device comprising a compound represented by Formula 1 above.

In the present invention, "alkyl" refers to a monovalent substituent derived from a saturated hydrocarbon having 1 to 40 carbon atoms in a straight or branched chain. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, "alkenyl (alkenyl)" refers to 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. Examples thereof include, but are not limited to, vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl) and the like.

In the present invention, "alkynyl" refers to 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. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, and 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'-, wherein R' means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. may include Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, "arylamine" means an amine substituted with aryl having 6 to 40 carbon atoms.

In the present invention, "cycloalkyl" 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.

In the present invention, "heterocycloalkyl" 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, S or a hetero atom such as 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 40 carbon atoms.

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

Since the compound represented by Formula 1 of the present invention has excellent thermal stability and light emitting properties, it can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having superior light emitting performance, low driving voltage, high efficiency and long lifespan can be manufactured compared to conventional host materials, and further Full color display panels with improved performance and lifetime can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. Novel Organic Compounds

The present invention provides a novel perimidine-based compound having superior driving voltage characteristics and efficiency while having a molecular weight higher than that of a conventional organic EL device material [eg, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)].

The novel perimidine-based organic light emitting compound of the present invention may be represented by the following formula (1).

[Formula 1]

In Formula 1,

X ₁ is C(R), or N;

R and R _{1 To} R ₇ are the same as or different from each other, and 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 of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ 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 of an aryl boron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group selected from the group consisting of,

Ar ₁ is a 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, C ₆ ~ C ₆₀ Aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ 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 Arylphosphine group, C ₆ ~ C ₆₀ Mono or diarylphosphine group It is selected from the group consisting of a pinyl group and a C ₆ ~ C _{60 arylamine group,}

R and R ₁ , R and R ₂ , R ₁ and Ar ₁ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ and R ₇ and Ar _One of 1 may combine with each other to form a condensed heteroaromatic ring including at least one of N, O, S, and Si, or a condensed aromatic ring.

The Ar ₁ , R And R _{1 To} R ₇ Alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron Group, arylphosphine group, mono or diarylphosphinyl group and arylamine group are each independently, 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 of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 ~ aryl phosphonium pingi of C _60, which may be substituted with at least one member selected from the group consisting of C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl amine. When substituted with a plurality of substituents, they may be the same as or different from each other.

The permidine-based organic light emitting compound of the present invention has excellent luminous efficiency and excellent material lifespan characteristics compared to the existing host material, which not only has a very excellent driving life of the device, but also induces an increase in power efficiency to produce an OLED device with improved power consumption. can be manufactured.

The perimidine-based compound has a wide energy band gap and has a chemically stable structure, so that functional groups having various functions are introduced, thereby having various energy band gaps and chemical properties. When an _{aromatic ring or a heteroaromatic ring is substituted at the Ar 1} position, there is an advantage as a phosphorescent host material that can improve electron mobility to balance holes and electrons in the light emitting layer, and maximize efficiency characteristics with a thermally stable structure.

According to one embodiment of the present invention Ar ₁ may be a substituent represented by the following formula (2) or a phenyl group.

[Formula 2]

In Formula 2,

* means a moiety bonded to Formula 1;

L is a single bond, or _{is selected from the group consisting of a C 6} ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, preferably a single bond, or a phenylene group or a biphenylene group; Y _{1 To} Y _{5 Are} the same as or different from each other, and each independently is N or C(R ₈ ), provided _{that at least one of Y 1 To} Y ₅ is N, and when R ₈ is plural, they are the same or different from each other, ;

R ₈ 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 ₆ ~ C ₄₀ aryl group, Heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ Aryloxy group C ₁ ~ C ₄₀ Alkyloxy group, C ₃ ~ C ₄₀ Cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ Mono or diarylphosphinyl group and C ₆ ~ C _{40 It} is selected from the group consisting of an arylsilyl group, or is _{combined with an adjacent group (eg, L, another adjacent R 8} ) to form a condensed ring can form;

Alkyl group of the R _8, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl 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 of alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ 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 ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ unsubstituted and, when the substituents are plural, they may be the same as or different from each other.

Examples of the substituent represented by Formula 2 include, but are not limited to, substituents represented by the following A-1 to A-15.

In the above A-1 to A-15,

L and R ₈ are each as defined in Formula 2 above,

n is an integer of 0 to 4, and when n is 0, _{it means that hydrogen is not substituted with a substituent R 9} , and when n is an integer of 1 to 4, R ₉ is 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 ~ C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C _{40 60} aryloxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ mono or diaryl phosphine of C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ P It is selected from the group consisting of a nyl group and a C ₆ ~ C _{40 arylsilyl group, or may be combined with an adjacent group (eg, L, R 8} or other R _9, etc.) to form a condensed ring,

Alkyl group of the R _9, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an 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 of alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ 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 ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ unsubstituted and, when the substituents are plural, they may be the same as or different from each other.

On the other hand, the compounds of the present invention are R and R ₁ , R and R ₂ , R ₁ and Ar ₁ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R _{One of 7} and R ₇ and Ar ₁ may be combined with each other to form a condensed heteroaromatic ring including at least one of N, O, S, and Si, or a condensed aromatic ring. Specifically, R and R ₁ , R and R ₂ , R ₁ and Ar ₁ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ and R ₇ and Ar ₁ may combine with each other to form condensed benzene, condensed indole, condensed benzothiophene, condensed benzofuran, condensed indene group, and the like.

In particular, R and R ₁ , R and R ₂ , R ₁ and Ar ₁ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ and R ₇ and Ar ₁ may be combined with each other to form Formula 3 below.

[Formula 3]

In the above formula,

The dotted line is the part where the condensation takes place,

X ₂ is selected from the group consisting of C(Ar ₂ )(Ar ₃ ), N(Ar ₄ ), O, S;

R ₁₀ to R ₁₃ are the same as or different from each other, and 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 ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ 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 phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in the, form a condensed ring by combining adjacent tile can do,

Ar _{2 To} Ar _{4 Are} the same as or different from each other, and each independently a 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 ~ C ₆₀ Aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ 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 phosphine group , C ₆ ~ C ₆₀ Mono or diarylphosphinyl group and C ₆ ~ C ₆₀ Selected from the group consisting of an arylamine group,

The R _{10 To} R ₁₃ And Ar _{2 To} Ar ₄ An alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, aryl A boron group, an arylphosphine group, a mono or diarylphosphinyl group and an arylamine group are each independently, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 phosphine group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group, and C ₆ ~ C ₆₀ It may be substituted with one or more selected from the group consisting of an arylamine group. In this case, when substituted with a plurality of substituents, they may be the same or different from each other.

In a preferred embodiment of the present invention, Ar ₂ to Ar ₄ may be a substituent represented by Formula 2 or a phenyl group.

In addition, the compound of the present invention may preferably be embodied as a compound of the following formula (4) or formula (5).

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 4 to 7,

X ₁ , X ₂ , R ₁ to R ₇ , and R ₁₀ to R ₁₃ are the same as defined in Formulas 1 and 3.

According to one embodiment of the present invention, in Chemical Formulas 4 to 7, X ₂ may be N(Ar ₄ ), O, or S, and is preferably _{N(Ar 4 ).}

In this case, Ar ₄ may be a substituent represented by Formula 2 or a phenyl group.

The compound of the present invention may be specifically represented by compounds having the structures exemplified below, but is not limited thereto.

2. Organic electroluminescent device

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) including the compound represented by Formula 1 according to the present invention.

More specifically, the organic electroluminescent device according to the present invention includes 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 a compound represented by Formula 1 above. In this case, the compound may be used alone, or two or more may be used in combination.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer, and at least one organic material layer may include a compound represented by Formula 1 above. have. Specifically, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer, an electron transport layer, and a hole transport layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and in this case, the compound of Formula 1 may be included as the host material. In addition, the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked. At this time, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, preferably a hole transport layer, an electron blocking layer, light emission The auxiliary layer may include a compound represented by Formula 1 above. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted between the electrode and the organic material layer interface.

The organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer contains the compound represented by Formula 1 above.

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 used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films and sheets may be used.

In addition, examples of the anode material include 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 SnO2: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, examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO2/Al, but is not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and common materials known in the art may be used.

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] Synthesis of A1

<Step 1> Synthesis of Al

Naphthalene-1,8-diamine, 11.4 g (72.1 mmol), formic acid, 16.0 ml (418.6 mmol), and ethanol 30 ml were added under a nitrogen stream and stirred at 75° C. for 3 hours.

After completion of the reaction, 2N K ₂ CO ₃ was used for neutralization, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound A1, (9.8 g, 58.4 mmol, yield 81%).

GC-Mass (theoretical: 168.19 mol, measured: 168 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 7.11 (d, 1H), 7.37 to 7.39 (m, 1H), 7.40 to 7.42 (m, 1H), 7.44 (d, 1H), 7.53 (s, 1H) ), 7.61 (d, 1H), 8.08 (d, 1H)

[Preparation Example 2] Synthesis of A3

<Step 1> Synthesis of A2

In a nitrogen stream A1 9.8g (58.4 mmol), 1- bromo-2-nitro-benzene, 35.4g (175.1 mmol), Cu powder, 2.6g (40.9 mmol), K 2 CO 3, 16.1g (116.7 mmol) , and 80 ml of nitrobenzene were mixed and stirred at 200 °C for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A2, (12.5 g, 740.0 mmol, yield 79%).

GC-Mass (theoretical: 289.39 g/mol, measured: 289 g/mol)

¹ H-NMR: δ 7.10 (d, 1H), 7.37 to 7.39 (m, 1H), 7.40 to 7.42 (m, 1H), 7.38 to 7.40 (m, 1H), 7.44 (d, 1H), 7.53 (s) , 1H), 7.61 (d, 1H), 8.08 (d, 1H), 8.12 (d, 1H), 8.14 to 8.16 (m, 1H), 8.50 (d, 1H)

<Step 2> Synthesis of A3

Under a nitrogen stream, 12.4 g (43.2 mmol) of A2, triphenylphosphine, 28.3 g (107.9 mmol), and 140 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A3, (8.0 g, 31.1 mmol, yield 72%).

GC-Mass (theoretical: 257.29 g/mol, measured: 257 g/mol)

¹ H-NMR: δ 5.1 (s, 1H), 7.10 (d, 1H), 7.37 to 7.39 (m, 1H), 7.40 to 7.42 (m, 1H), 7.38 to 7.40 (m, 1H), 7.44 (d) , 1H), 7.61 (d, 1H), 8.08 (d, 1H), 8.12 (d, 1H), 8.14 to 8.16 (m, 1H), 8.50 (d, 1H)

[Preparation Example 3] Synthesis of B1

<Step 1> Synthesis of B1

Acenaphthylene, 30.0 g (197.1 mmol), 30 ml of 0.25MH ₂ SO ₄ and 800 ml of 0.8N-hydrazoic acid were added under a nitrogen stream and stirred at 50° C. for 3 hours.

After completion of the reaction, 2N K ₂ CO ₃ was used for neutralization, and then water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound B1, (3.9 g, 32.9 mmol, yield 12%).

GC-Mass (theoretical: 167.21 g/mol, measured: 167 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 5.61 (d, 1H), 6.33 (d, 1H), 7.10 (d, 1H), 7.36 to 7.38 (m, 1H), 7.40 to 7.42 (m, 1H) ), 7.52 (d, 1H), 7.74 (d, 1H), 8.02 (d, 1H)

[Preparation Example 4] Synthesis of B3

<Step 1> Synthesis of B2

B1 3.9 g (23.7 mmol), 1-bromo-2-nitrobenzene, 14.3 g (70.9 mmol), Cu powder, 1.1 g (16.6 mmol), K ₂ CO _3, 6.5 g (47.3 mmol) under a nitrogen stream , and 30 ml of nitrobenzene were mixed and stirred at 200 °C for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound B2, (5.3 g, 18.2 mmol, yield 77%).

GC-Mass (Theory: 288.30 g/mol, Measured: 288 g/mol)

¹ H-NMR: δ 5.61 (d, 1H), 6.33 (d, 1H), 7.10 (d, 1H), 7.36 to 7.38 (m, 1H), 7.40 to 7.42 (m, 1H), 7.44 (m, 1H) ), 7.52 (d, 1H), 7.74 (d, 1H), 8.02 (d, 1H), 8.04 (d, 1H), 8.11 to 8.13 (m, 1H), 8.51 (d, 1H)

<Step 2> Synthesis of B3

Under a nitrogen stream, 5.3 g (18.2 mmol) of B2, triphenylphosphine, 11.9 g (45.5 mmol), and 50 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound B3, (3.5 g, 13.5 mmol, yield 74%).

GC-Mass (theoretical: 256.30 g/mol, measured: 256 g/mol)

¹ H-NMR: δ 5.01 (s, 1H), 7.20-22 (m, 2H), 7.24 (s, 1H), 7.40 (d, 1H), 7.44 (m, 1H), 7.52 (d, 1H), 7.65 (d, 1H), 7.83 (d, 1H), 7.91 to 7.93 (m, 1H), 8.51 (d, 1H), 8.60 (d, 1H)

[Preparation Example 5] Synthesis of C2

<Step 1> Synthesis of Al

Naphthalene-1,8-diamine, 11.4 g (72.1 mmol), formic acid, 16.0 ml (418.6 mmol), and ethanol 30 ml were added under a nitrogen stream and stirred at 75° C. for 3 hours.

After completion of the reaction, 2N K ₂ CO ₃ was used for neutralization, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound A1 (9.8 g, 58.4 mmol, yield 81%).

GC-Mass (theoretical: 168.19 mol, measured: 168 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 7.11 (d, 1H), 7.37 to 7.39 (m, 1H), 7.40 to 7.42 (m, 1H), 7.44 (d, 1H), 7.53 (s, 1H) ), 7.61 (d, 1H), 8.08 (d, 1H)

<Step 2> Synthesis of C1

A1 9.8g (58.4 mmol), NBS (N-bromosuccinimide), 10.4g (58.4 mmol), and 100 ml of DMF were mixed under a nitrogen stream and stirred at 60° C. for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound C1, (11.1 g, 44.9 mmol, yield 77%).

GC-Mass (theoretical: 247.09 g/mol, measured: 247 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 6.95 (d, 1H), 7.47 to 7.48 (m, 2H), 7.49 (s, 1H), 7.67 (t, 1H), 8.01 (m, 1H)

<Step 3> Synthesis of C2

Under a nitrogen stream, C1, 11.1 g, (44.9 mmol), phenylboronic acid, 5.5 g (44.9 mmol), 2.6 g (5 mol%) of Pd(PPh ₃ ) ₄ , and potassium carbonate, 18.6 g (134.8 mmol) and 80ml/40ml/40ml of toluene/H ₂ O/ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound C2, (8.7 g, 35.5 mmol, yield 79%).

GC-Mass (theoretical: 244.29 g/mol, measured: 244 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 6.95 (d, 1H), 7.42 to 7.51 (m, 7H), 7.49 (s, 1H), 7.67 (t, 1H), 8.01 (m, 1H)

[Preparation Example 6] Synthesis of D3

<Step 1> Synthesis of Al

Naphthalene-1,8-diamine, 11.4 g (72.1 mmol), formic acid, 16.0 ml (418.6 mmol), and ethanol 30 ml were added under a nitrogen stream and stirred at 75° C. for 3 hours.

After completion of the reaction, 2N K ₂ CO ₃ was used for neutralization, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound A1 (9.8 g, 58.4 mmol, yield 81%).

GC-Mass (theoretical: 168.19 mol, measured: 168 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 7.11 (d, 1H), 7.37 to 7.39 (m, 1H), 7.40 to 7.42 (m, 1H), 7.44 (d, 1H), 7.53 (s, 1H) ), 7.61 (d, 1H), 8.08 (d, 1H)

<Step 2> Synthesis of C1

A1 9.8g (58.4 mmol), NBS (N-bromosuccinimide), 10.4g (58.4 mmol), and 100 ml of DMF were mixed under a nitrogen stream and stirred at 60° C. for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound C1 (11.1 g, 44.9 mmol, yield 77%).

GC-Mass (theoretical: 247.09 g/mol, measured: 247 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 6.95 (d, 1H), 7.47 to 7.48 (m, 2H), 7.49 (s, 1H), 7.67 (t, 1H), 8.01 (m, 1H)

<Step 3> Synthesis of D1

Under a nitrogen stream, C1, 11.1 g (44.9 mmol), iodobenzene, 27.5 g (134.5 mmol), Cu powder, 2.0 g (31.5 mmol), K ₂ CO _3, 12.4 g (89.9 mmol), nitrobenzene 100 ml were mixed and stirred at 200 °C for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound D1 (11.5 g, 35.5 mmol, yield 79%).

GC-Mass (theoretical: 323.19 g/mol, measured: 323 g/mol)

¹ H-NMR: δ 6.28 to 6.29 (m, 2H), 6.80 (m, 1H), 6.95 (d, 1H), 7.18 to 7.19 (m, 2H), 7.44 to 7.45 (m, 2H), 7.49 (s) , 1H), 7.67 (t, 1H), 8.01 (m, 1H)

<Step 4> Synthesis of D2

D1, 11.5 g, (35.5 mmol), 2-nitrophenylboronic acid, 5.9 g (35.5 mmol), 2.0 g (5 mol%) of Pd(PPh ₃ ) ₄ , and potassium carbonate, 14.7 g ( 106.5 mmol) and 80ml/40ml/40ml of toluene/H ₂ O/ethanol were added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound D2 (10.4 g, 28.4 mmol, yield 80%).

¹ H-NMR: δ 6.28 to 6.29 (m, 2H), 6.80 (m, 1H), 6.95 (d, 1H), 7.18 to 7.19 (m, 2H), 7.44 to 7.45 (m, 2H), 7.49 (s) , 1H), 7.67~7.69(t, 2H), 7.88(m, 1H), 8.01~8.03(m, 3H)

<Step 5> Synthesis of D3

10.4 g (28.4 mmol) of D2, 18.6 g (71.0 mmol), and 100 ml of 1,2-dichlorobenzene were added under a nitrogen stream, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound D3 (7.1 g, 21.3 mmol, yield 75%).

GC-Mass (theoretical: 333.39 g/mol, measured: 333 g/mol)

¹ H-NMR: δ 6.28 to 6.29 (m, 2H), 6.80 (m, 1H), 6.95 (d, 1H), 7.18 to 7.19 (m, 2H), 7.28 (m, 1H), 7.44 to 7.45 (m) , 2H), 7.49(s, 1H), 7.50(m, 1H), 7.64(d, 1H), 8.07(m, 1H), 8.12(d, 1H), 10.01(s, 1H)

[Preparation Example 7] Synthesis of E3

<Step 1> Synthesis of Al

Naphthalene-1,8-diamine, 11.4 g (72.1 mmol), formic acid, 16.0 ml (418.6 mmol), and ethanol 30 ml were added under a nitrogen stream and stirred at 75° C. for 3 hours.

After completion of the reaction, 2N K ₂ CO ₃ was used for neutralization, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound A1 (9.8 g, 58.4 mmol, yield 81%).

GC-Mass (theoretical: 168.19 mol, measured: 168 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 7.11 (d, 1H), 7.37 to 7.39 (m, 1H), 7.40 to 7.42 (m, 1H), 7.44 (d, 1H), 7.53 (s, 1H) ), 7.61 (d, 1H), 8.08 (d, 1H)

<Step 2> Synthesis of E1

Under a nitrogen stream, A1, 9.8 g (58.45 mmol), iodobenzene, 41.4 g (175.1 mmol), Cu powder, 2.6 g (40.9 mmol), K ₂ CO _3, 16.1 g (116.7 mmol), nitrobenzene 100 ml were mixed and stirred at 200 °C for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound E1 (12.3 g, 37.9 mmol, yield 65%).

GC-Mass (theoretical: 323.73 g/mol, measured: 323 g/mol)

¹ H-NMR: δ 6.71 (d, 1H), 7.07 (s, 1H), 7.11 (d, 1H), 7.37 to 7.39 (m, 1H), 7.40 to 7.42 (m, 1H), 7.44 (d, 1H) ), 7.53 (s, 1H), 7.61 (d, 1H), 7.94 (d, 1H), 8.08 (d, 1H)

<Step 3> Synthesis of E2

Under a nitrogen stream, 12.3 g (28.4 mmol) of E1, triphenylphosphine, 24.5 g (24.8 mmol), and 100 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound E2 (8.1 g, 27.7 mmol, yield 73%).

GC-Mass (theoretical: 291.73 g/mol, measured: 291 g/mol)

¹ H-NMR: δ 5.0 (s, 1H), 7.11 (d, 1H), 7.51 (d, 1H), 7.57 (d, 2H), 7.83 (t, 2H), 8.15 (d, 2H), 8.35 ( s, 1H)

<Step 3> Synthesis of E3

Under a nitrogen stream, E2, 8.1 g, (27.7 mmol), phenylboronic acid, 3.4 g (27.7 mmol), 1.6 g (5 mol%) of Pd(PPh ₃ ) ₄ , and potassium carbonate, 11.5 g (83.1 mmol) and 80ml/40ml/40ml of toluene/H ₂ O/ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound E3 (7.6 g, 22.7 mmol, yield 82%).

GC-Mass (theoretical: 333.39 g/mol, measured: 333 g/mol)

¹ H-NMR: δ 5.0 (s, 1H), 7.40 (m, 1H), 7.50 to 7.52 (m, 4H), 7.57 (d, 2H), 7.65 (d, 1H), 7.83 (t, 2H), 7.90(s, 1H), 8.05(d, 1H), 8.15(d, 2H)

[Preparation Example 8] Synthesis of C2

<Step 1> Synthesis of B1

Acenaphthylene, 30.0 g (197.1 mmol), 30 ml of 0.25MH ₂ SO ₄ and 800 ml of 0.8N-hydrazoic acid were added under a nitrogen stream and stirred at 50° C. for 3 hours.

After completion of the reaction, 2N K ₂ CO ₃ was used for neutralization, and then water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound B1 (3.9 g, 32.9 mmol, yield 12%).

GC-Mass (theoretical: 167.21 g/mol, measured: 167 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 5.61 (d, 1H), 6.33 (d, 1H), 7.10 (d, 1H), 7.36 to 7.38 (m, 1H), 7.40 to 7.42 (m, 1H) ), 7.52 (d, 1H), 7.74 (d, 1H), 8.02 (d, 1H)

<Step 2> Synthesis of F1

B1 34.0g (23.7 mmol), NBS (N-bromosuccinimide), 4.2g (23.7 mmol), and 100 ml of DMF were mixed under a nitrogen stream and stirred at 60° C. for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound F1 (4.4 g, 17.7 mmol, yield 75%).

GC-Mass (theoretical: 246.21 g/mol, measured: 246 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 5.61 (d, 1H), 6.33 (d, 1H), 6.68 (s, 1H), 7.53 (m, 1H), 7.65 (s, 1H), 7.80 ( d, 1H), 7.90 (d, 1H)

<Step 3> Synthesis of F2

F1, 4.4 g, (17.7 mmol), phenylboronic acid, 2.2 g (17.7 mmol), 1.0 g (5 mol%) of Pd(PPh ₃ ) ₄ , and potassium carbonate, 7.3 g (53.2 mmol) under a nitrogen stream and 80ml/40ml/40ml of toluene/H ₂ O/ethanol was added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound F2 (3.4 g, 14.0 mmol, yield 79%).

GC-Mass (theoretical: 243.3 g/mol, measured: 2443 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 5.61 (d, 1H), 6.33 (d, 1H), 6.68 (s, 1H), 7.40 (m, 1H), 7..49 to 7.52 (m, 6H), 7.65(s, 1H), 7.80(d, 1H), 7.90(d, 1H)

[Preparation Example 9] Synthesis of G3

<Step 1> Synthesis of B1

Acenaphthylene, 30.0 g (197.1 mmol), 30 ml of 0.25MH ₂ SO ₄ and 800 ml of 0.8N-hydrazoic acid were added under a nitrogen stream and stirred at 50° C. for 3 hours.

After completion of the reaction, 2N K ₂ CO ₃ was used for neutralization, and then water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound B1 (3.9 g, 32.9 mmol, yield 12%).

GC-Mass (theoretical: 167.21 g/mol, measured: 167 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 5.61 (d, 1H), 6.33 (d, 1H), 7.10 (d, 1H), 7.36 to 7.38 (m, 1H), 7.40 to 7.42 (m, 1H) ), 7.52 (d, 1H), 7.74 (d, 1H), 8.02 (d, 1H)

<Step 2> Synthesis of F1

B1 34.0g (23.7 mmol), NBS (N-bromosuccinimide), 4.2g (23.7 mmol), and 100 ml of DMF were mixed under a nitrogen stream and stirred at 60° C. for 3 hours.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound F1 (4.4 g, 17.7 mmol, yield 75%).

GC-Mass (theoretical: 246.21 g/mol, measured: 246 g/mol)

¹ H-NMR: δ 4.1 (s, 1H), 5.61 (d, 1H), 6.33 (d, 1H), 6.68 (s, 1H), 7.53 (m, 1H), 7.65 (s, 1H), 7.80 ( d, 1H), 7.90 (d, 1H)

<Step 3> Synthesis of G1

F1, 4.4 g (17.7 mmol), iodobenzene, 10.9 g (53.2 mmol), Cu powder, 0.8 g (12.4 mmol), K ₂ CO _3, 4.9 g (35.5 mmol), nitrobenzene under a nitrogen stream, 50 ml were mixed and stirred at 200 °C for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound G1 (4.5 g, 14.0 mmol, yield 79%).

GC-Mass (theoretical: 322.20 g/mol, measured: 322 g/mol)

¹ H-NMR: δ 5.61 (d, 1H), 6.27 to 6.28 (d, 2H), 6.33 (d, 1H), 6.68 (s, 1H), 6.80 (m, 1H), 7.20 to 7.21 (m, 2H) ), 7.53(m, 1H), 7.65(s, 1H), 7.80(d, 1H), 7.90(d, 1H)

<Step 4> Synthesis of G2

G1, 4.1 g, (14.0 mmol), 2-nitrophenylboronic acid, 2.3 g (14.0 mmol), 0.8 g (5 mol%) of Pd(PPh ₃ ) ₄ , and potassium carbonate, 5.8 g ( 42.1 mmol) and 80ml/40ml/40ml of toluene/H ₂ O/ethanol were added and stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound G2 (4.1 g, 11.4 mmol, yield 81%).

GC-Mass (theoretical: 364.4 g/mol, measured: 364 g/mol)

¹ H-NMR: δ 5.61 (d, 1H), 6.27 to 6.28 (d, 2H), 6.33 (d, 1H), 6.68 (s, 1H), 6.80 (m, 1H), 7.20 to 7.21 (m, 2H) ), 7.53(m, 1H), 7.65(s, 1H), 7.67(m, 1H), 7.80(d, 1H), 7.90(d, 1H), 7.92(m, 1H), 8.02~8.04(m, 2H)

<Step 5> Synthesis of G3

Under a nitrogen stream, 4.1 g (11.4 mmol) of G2, triphenylphosphine, 7.4 g (28.4 mmol), and 50 ml of 1,2-dichlorobenzene were added, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using _{MgSO 4 .} After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound G3 (2.7 g, 8.1 mmol, yield 71%).

GC-Mass (theoretical: 332.39 g/mol, measured: 332 g/mol)

¹ H-NMR: δ 5.61 (d, 1H), 6.27 to 6.28 (d, 2H), 6.68 (s, 1H), 7.04 (s, 1H), 7.20 to 7.21 (m, 2H), 7.53 (m, 1H) ), 7.65(s, 1H), 7.67(m, 1H), 7.80(d, 1H), 7.90(d, 1H), 7.92(m, 1H), 8.02~8.04(m, 2H), 10.01(s, 1H)

[Synthesis Example 1] Synthesis of R1

A1, 9.8g (58.4mmol), 5'-chloro-1,1':3', 1''-terphenyl, 17.0g (64.2mmol), 2.8g (5 mol%) of Pd ₂ ( dba) ₃ , tri- tert -butylphosphine, 0.6 g (0.6 mmol) and sodium tert-butoxide, 16.8 g (175.1 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R1, 14.1g (35.6mmol, yield 61%).

GC-Mass (theoretical: 396.48 g/mol, measured: 396 g/mol)

[Synthesis 2] Synthesis of R2

A1, 9.8 g (58.4 mmol), 2-chloro-4,6-diphenylpyrimidine, 17.1 g (64.2 mmol), 2.8 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert under a nitrogen stream -Butylphosphine, 0.6 g (0.6 mmol) and sodium tert-butoxide, 16.8 g (175.1 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R2, 14.7g (36.8mmol, yield 63%).

GC-Mass (theoretical: 398.46 g/mol, measured: 398 g/mol)

[Synthesis 3] Synthesis of R3

A1, 9.8 g (58.4 mmol), 2'-chloro-6'-phenyl-2,4'-bipyridine, 17.1 g (64.2 mmol), 2.8 g (5 mol%) of Pd ₂ (dba) under a nitrogen stream ₃ , tri- tert -butylphosphine, 0.6 g (0.6 mmol) and sodium tert-butoxide, 16.8 g (175.1 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R3, 15.6 g (39.1 mmol, yield 67%).

GC-Mass (theoretical: 398.46 g/mol, measured: 398 g/mol)

[Synthesis Example 4] Synthesis of R20

A1, 9.8 g (58.4 mmol), 2'-chloro-6'-phenyl-2,4'-bipyridine, 22.4 g (64.2 mmol), 2.8 g (5 mol%) of Pd ₂ (dba) under a nitrogen stream ₃ , tri- tert -butylphosphine, 0.6 g (0.6 mmol) and sodium tert-butoxide, 16.8 g (175.1 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R20, 17.8 g (37.4 mmol, yield 64%).

GC-Mass (theoretical: 475.54 g/mol, measured: 475 g/mol)

[Synthesis Example 5] Synthesis of R25

A1, 9.8 g (58.4 mmol), 2-chloro-4-phenylquinazoline, 15.5 g (64.2 mmol), 2.8 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine under a nitrogen stream , 0.6 g (0.6 mmol) and sodium tert-butoxide, 16.8 g (175.1 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R20, 13.9g (37.4mmol, yield 64%).

GC-Mass (theoretical: 372.42 g/mol, measured: 372 g/mol)

[Synthesis Example 6] Synthesis of R26

B1, 3.9g (23.7mmol), 5'-chloro-1,1':3',1''-terphenyl, 6.9g (26.0mmol), 1.1g (5 mol%) of Pd ₂ ( dba) ₃ , tri- tert -butylphosphine, 1.2 g (1.2 mmol) and sodium tert-butoxide, 6.8 g (70.9 mmol) and 80 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R26, 5.7g (14.4mmol, yield 61%).

GC-Mass (theoretical: 395.49 g/mol, measured: 395 g/mol)

[Synthesis 7] Synthesis of R27

B1, 3.9 g (23.7 mmol), 2-chloro-4,6-diphenylpyrimidine, 6.9 g (26.0 mmol), 1.1 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert under a nitrogen stream -Butylphosphine, 1.2g (1.2mmol) and sodium tert-butoxide, 6.8g (70.9mmol) and 80ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R27, 5.7g (14.4mmol, yield 61%).

GC-Mass (theoretical: 397.47 g/mol, measured: 397 g/mol)

[Synthesis 8] Synthesis of R28

B1, 3.9 g (23.7 mmol), 2'-chloro-6'-phenyl-2,4'-bipyridine, 6.9 g (26.0 mmol), 1.1 g (5 mol%) of Pd ₂ (dba) under a nitrogen stream ₃ , tri- tert -butylphosphine, 1.2 g (1.2 mmol) and sodium tert-butoxide, 6.8 g (70.9 mmol) and 80 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R28, 8.9g (14.9mmol, yield 63%).

GC-Mass (theoretical: 397.47 g/mol, measured: 397 g/mol)

[Synthesis Example 9] Synthesis of R45

B1, 3.9 g (23.7 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 8.9 g (26.0 mmol), 1.1 g (5 mol%) under a nitrogen stream ) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 1.2 g (1.2 mmol) and sodium tert-butoxide, 6.8 g (70.9 mmol) and 80 ml of toluene were added and stirred at 110° C. for 4 hours. .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R45, 7.1g (14.9mmol, yield 63%).

GC-Mass (Theory: 474.55 g/mol, Measured: 474 g/mol)

[Synthesis Example 10] Synthesis of R50

B1, 3.9g (23.7mmol), 2-chloro-4-phenylquinazoline, 6.3g (26.0mmol), 1.1g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphos under a nitrogen stream Pin, 1.2 g (1.2 mmol) and sodium tert-butoxide, 6.8 g (70.9 mmol) and 80 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R50, 5.7g (15.4mmol, yield 65%).

GC-Mass (theoretical: 371.43 g/mol, measured: 371 g/mol)

[Synthesis Example 11] Synthesis of R51

A3, 8.0g (31.1mmol), 5'-chloro-1,1':3',1''-terphenyl, 9.1g (34.2mmol), 1.5g (5 mol%) of Pd ₂ ( dba) ₃ , tri- tert -butylphosphine, 0.3 g (1.6 mmol) and sodium tert-butoxide, 8.9 g (93.3 mmol) and 160 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R51, 9.2g (19.0mmol, yield 61%).

GC-Mass (theoretical: 485.58 g/mol, measured: 485 g/mol)

[Synthesis 12] Synthesis of R52

A3, 8.0 g (31.1 mmol), 2-chloro-4,6-diphenylpyrimidine, 9.1 g (34.2 mmol), 1.5 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert under a nitrogen stream -Butylphosphine, 0.3 g (1.6 mmol) and sodium tert-butoxide, 8.9 g (93.3 mmol) and 160 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R52, 10.3g (21.1mmol, yield 68%).

GC-Mass (theoretical: 487.55 g/mol, measured: 487 g/mol)

[Synthesis 13] Synthesis of R53

A3, 8.0 g (31.1 mmol), 2'-chloro-6'-phenyl-2,4'-bipyridine, 9.1 g (34.2 mmol), 1.5 g (5 mol%) of Pd ₂ (dba) under a nitrogen stream ₃ , tri- tert -butylphosphine, 0.3 g (1.6 mmol) and sodium tert-butoxide, 8.9 g (93.3 mmol) and 160 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R53, 10.3g (21.1mmol, yield 68%).

GC-Mass (theoretical: 487.55 g/mol, measured: 487 g/mol)

[Synthesis Example 14] Synthesis of R70

A3, 8.0 g (31.1 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 11.8 g (34.2 mmol), 1.5 g (5 mol%) under a nitrogen stream ) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.3 g (1.6 mmol) and sodium tert-butoxide, 8.9 g (93.3 mmol) and 160 ml of toluene were added and stirred at 110° C. for 4 hours. .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R70, 11.4 g (20.2 mmol, yield 65%).

GC-Mass (theoretical: 564.64 g/mol, measured: 564 g/mol)

[Synthesis Example 15] Synthesis of R75

A3, 8.0g (31.1mmol), 2-chloro-4-phenylquinazoline, 11.8g (34.2mmol), 1.5g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphos under a nitrogen stream Pin, 0.3 g (1.6 mmol) and sodium tert-butoxide, 8.9 g (93.3 mmol) and 160 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R75, 9.3g (20.2mmol, yield 65%).

GC-Mass (theoretical: 461.52 g/mol, measured: 461 g/mol)

[Synthesis Example 16] Synthesis of R76

B3, 3.5g (13.5mmol), 5'-chloro-1,1':3',1''-terphenyl, 3.9g (14.8mmol), 0.6g (5 mol%) of Pd ₂ ( dba) ₃ , tri- tert -butylphosphine, 0.1 g (0.7 mmol) and sodium tert-butoxide, 3.9 g (40.4 mmol) and 70 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R76, 4.2g (8.6mmol, yield 64%).

GC-Mass (Theory: 484.59 g/mol, Measured: 484 g/mol)

[Synthesis 17] Synthesis of R77

B3, 3.5 g (13.5 mmol), 2-chloro-4,6-diphenylpyrimidine, 3.9 g (14.8 mmol), 0.6 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert under a nitrogen stream -Butylphosphine, 0.1 g (0.7 mmol) and sodium tert-butoxide, 3.9 g (40.4 mmol) and 70 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R77, 4.0g (8.2mmol, yield 61%).

GC-Mass (Theory: 486.57 g/mol, Measured: 486 g/mol)

[Synthesis 18] Synthesis of R79

B3, 3.5g (13.5mmol), 2'-chloro-6'-phenyl-2,4'-bipyridine, 3.9g (14.8mmol), 0.6g (5 mol%) of Pd ₂ (dba) under a nitrogen stream ₃ , tri- tert -butylphosphine, 0.1 g (0.7 mmol) and sodium tert-butoxide, 3.9 g (40.4 mmol) and 70 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R78, 4.1g (8.4mmol, yield 62%).

GC-Mass (Theory: 486.57 g/mol, Measured: 486 g/mol)

[Synthesis Example 19] Synthesis of R95

B3, 3.5 g (13.5 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 5.1 g (14.8 mmol), 0.6 g (5 mol%) under a nitrogen stream ) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.1 g (0.7 mmol) and sodium tert-butoxide, 3.9 g (40.4 mmol) and 70 ml of toluene were added and stirred at 110° C. for 4 hours. .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R95, 5.1g (9.0mmol, yield 67%).

GC-Mass (theoretical: 563.65 g/mol, measured: 563 g/mol)

[Synthesis Example 20] Synthesis of R100

B3, 3.5g (13.5mmol), 2-chloro-4-phenylquinazoline, 3.6g (14.8mmol), 0.6g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphos under a nitrogen stream Pin, 0.1 g (0.7 mmol) and sodium tert-butoxide, 3.9 g (40.4 mmol) and 70 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R100, 4.2g (9.0mmol, yield 67%).

GC-Mass (theoretical: 460.53 g/mol, measured: 460 g/mol)

[Synthesis Example 21] Synthesis of R101

C2 under a nitrogen stream, 8.7 g (35.5 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 10.3 g (39.1 mmol), 1.7 g (5 mol%) ) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.4 g (1.8 mmol) and sodium tert-butoxide, 10.2 g (106.5 mmol) and 100 ml of toluene were added and stirred at 110° C. for 4 hours. .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R101, 12.5g (22.7mmol, yield 64%).

GC-Mass (theoretical: 551.64 g/mol, measured: 551 g/mol)

[Synthesis Example 22] Synthesis of R126

D3, 7.1 g (21.3 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 6.2 g (23.4 mmol), 1.0 g (5 mol%) under a nitrogen stream ) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.2 g (1.1 mmol) and sodium tert-butoxide, 6.1 g (63.9 mmol) and 100 ml of toluene were added and stirred at 110° C. for 4 hours. .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R126, 8.7 g (13.6 mmol, yield 64%).

GC-Mass (theoretical: 640.73 g/mol, measured: 640 g/mol)

[Synthesis Example 23] Synthesis of R151

E3, 7.6 g (22.7 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 6.6 g (25.0 mmol), 1.1 g (5 mol%) under a nitrogen stream ) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.2 g (1.1 mmol) and sodium tert-butoxide, 6.6 g (68.1 mmol) and 100 ml of toluene were added and stirred at 110° C. for 4 hours. .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R151, 9.6g (15.0 mmol, yield 66%).

GC-Mass (theoretical: 640.73 g/mol, measured: 640 g/mol)

[Synthesis Example 24] Synthesis of R176

F2, 3.4 g (14.0 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 4.1 g (15.4 mmol), 0.7 g (5 mol%) under a nitrogen stream ) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.1 g (0.7 mmol) and sodium tert-butoxide, 4.0 g (42.0 mmol) and 100 ml of toluene were added and stirred at 110° C. for 4 hours. .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R176, 4.8g (8.7 mmol, yield 62%).

GC-Mass (theoretical: 550.65 g/mol, measured: 550 g/mol)

[Synthesis Example 25] Synthesis of R201

G3, 2.7 g (8.1 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 2.4 g (8.9 mmol), 0.4 g (5 mol%) under a nitrogen stream ) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.1 g (0.4 mmol) and sodium tert-butoxide, 2.3 g (24.2 mmol) and 100 ml of toluene were added and stirred at 110° C. for 4 hours. .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R201, 3.2g (5.0 mmol, yield 62%).

GC-Mass (theoretical: 639.75 g/mol, measured: 639 g/mol)

[Synthesis Example 26] Synthesis of R251

Under a nitrogen stream, A1, 9.8 g (58.4 mmol), diphenylamine, 10.9 g (64.2 mmol), 2.8 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.6 g (2.9) mmol) and sodium tert-butoxide, 16.8 g (175.1 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound R251, 11.9 g (35.6 mmol, yield 61%).

GC-Mass (theoretical: 335.40 g/mol, measured: 335 g/mol)

[Synthesis Example 27] Synthesis of R256

A3, 8.0 g (31.1 mmol), diphenylamine, 5.8 g (34.2 mmol), 1.5 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.3 g (1.6) under a nitrogen stream mmol) and sodium tert-butoxide, 8.9 g (93.3 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R256, 8.1g (19.0 mmol, yield 61%).

GC-Mass (theoretical: 424.50 g/mol, measured: 424 g/mol)

[Synthesis Example 28] Synthesis of R261

A2, 3.9 g (23.7 mmol), diphenylamine, 4.4 g (26.0 mmol), 1.1 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.2 g (1.2) under a nitrogen stream mmol) and sodium tert-butoxide, 6.8 g (71.0 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R261, 4.8g (14.4 mmol, yield 61%).

GC-Mass (theoretical: 334.41 g/mol, measured: 334 g/mol)

[Synthesis Example 29] Synthesis of R266

B3, 3.5 g (13.5 mmol), diphenylamine, 2.5 g (14.8 mmol), 0.6 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine, 0.1 g (0.7) under a nitrogen stream mmol) and sodium tert-butoxide, 3.9 g (40.4 mmol) and 200 ml of toluene were added and stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using _{MgSO 4 .} Purification by column chromatography gave the target compound, R266, 3.7g (8.6 mmol, yield 64%).

GC-Mass (theoretical: 423.51 g/mol, measured: 423 g/mol)

[Examples 1 to 17] Preparation of green organic EL device

The compound synthesized in Synthesis Example was subjected to high-purity sublimation purification by a commonly known method, and then a green organic EL device was manufactured according to the following procedure.

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

m-MTDATA (60 nm)/TCTA (80 nm)/ R1, R3, R20, R26, R28, R45, R51, R53, R70, T76, R78, R95, R101, R126, R151, Each compound of R201 and R226 + 10% Ir(ppy) ₃ (30 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) by stacking in the order of organic EL device was produced.

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

[Comparative Example 1] Preparation of green organic EL device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of compound R1 as a light emitting host material when the light emitting layer was formed.

[Evaluation Example 1]

For each green organic EL device manufactured in Examples 1 to 17 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of (10) mA/cm 2 were measured, and the results are shown in Table 1 below. It was.

Sample host drive voltage
(V) EL peak
(nm) current efficiency
(cd/A) Example 1 R1 6.2 515 41.4 Example 2 R3 6.3 515 41.8 Example 3 R20 5.8 515 42.4 Example 4 R26 6.1 514 40.3 Example 5 R28 5.9 515 40.5 Example 6 R45 5.8 515 42.2 Example 7 R51 6.4 513 40.7 Example 8 R53 6.1 515 40.6 Example 9 R70 5.9 515 42.8 Example 10 R76 6.8 514 41.3 Example 11 R78 6.2 514 41.0 Example 12 R95 5.5 515 42.5 Example 13 R53 6.1 515 40.6 Example 14 R70 5.9 515 42.8 Example 15 R76 6.8 514 41.3 Example 16 R78 6.2 514 41.0 Example 17 R95 5.5 515 42.5 Comparative Example 1 CBP 7.1 517 37.0

As shown in Table 1 above, the compounds (R1, R3, R20, R26, R28, R45, R51, R53, R70, T76, R78, R95, R101, R126, R151, R201, R226) according to the present invention are green It can be seen that when used as a light emitting layer of an organic EL device (Example 1-12), compared to a green organic EL device using conventional CBP (Comparative Example 2), better performance in terms of efficiency and driving voltage is shown.

[Examples 18 to 25] Fabrication of red organic EL device

After high-purity sublimation purification of the compound synthesized in Synthesis Example by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.

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

On the thus prepared ITO transparent electrode, m-MTDATA (60 nm)/TCTA (80 nm)/ R2, R25, R27, R50, R52, R75, R77, R100 compound + 10% (piq) ₂ Ir(acac) (30nm) )/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate an organic electroluminescent device.

[Comparative Example 2]

A red organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound of Synthesis Example 2 as a light emitting host material when the light emitting layer was formed.

The structures of m-MTDATA, (piq) ₂ Ir(acac), CBP and BCP used in Examples 18 to 25 and Comparative Example 2 are as follows.

[Evaluation Example 2]

The driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 18 to 25 and Comparative Example 2, and the results are shown in Table 2 below.

Sample host drive voltage
(V) EL peak
(nm) current efficiency
(cd/A) Example 18 R2 4.4 621 10.8 Example 19 R25 4.3 621 11.5 Example 20 R27 4.1 620 11.3 Example 21 R50 3.8 621 11.9 Example 22 R52 4.4 621 11.0 Example 23 R75 4.0 621 12.8 Example 24 R77 4.1 620 10.5 Example 25 R100 3.9 621 12.3 Comparative Example 2 CBP 5.5 622 9,1

As shown in Table 2, when the compound according to the present invention was used as a material for the light emitting layer of a red organic electroluminescent device (Examples 18 to 25), a conventional red organic electroluminescent device using CBP as a material for the light emitting layer (Comparative Example) 2), it can be seen that the performance is excellent in terms of efficiency and driving voltage.

[Examples 26 to 29] Preparation of green organic EL device

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is performed and dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed with UV for 5 minutes. Then, the substrate was transferred to a vacuum laminating machine.

m-MTDATA(60nm)/R251, R256, R261, R266(80nm)/DS-H522 + 5% DS-501(300nm)/BCP(10nm)/Alq3(30nm)/ An organic EL device was manufactured in the order of LiF (1 nm)/Al (200 nm).

DS-H522 and DS-501 used for device fabrication are products of Doosan Electronics BG. The structures of m-MTDATA, TCTA, CBP, Ir(ppy) ₃ , and BCP are as follows.

[Comparative Example 3]

An organic EL device was manufactured in the same manner as in Example 26, except that NPB was used instead of the compound R251 used as a hole transport layer material when the hole transport layer was formed. The structure of the NPB used is as follows.

[Evaluation Example 3]

For each of the organic electroluminescent devices manufactured in Examples 26 to 29 and Comparative Example 3, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 3 below.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example 26 R251 4.4 24.1 Example 27 R256 4.5 22.3 Example 28 R261 4.3 20.1 Example 29 R266 3.8 26.2 Comparative Example 3 NPB 5.2 18.0

As shown in Table 3, when the compound according to the present invention was used as an organic electroluminescent device for a hole transport layer (Examples 26 to 29), when compared with an organic electroluminescent device using a conventional NPB (Comparative Example 3), the efficiency and It can be seen that excellent performance is shown in terms of driving voltage.

Claims (12)

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

In Formula 1,
X ₁ is C(R), or N;
R and R _{1 To} R ₇ are the same as or different from each other, and 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 of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ 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 of an aryl boron group, a C ₆ -C ₆₀ arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;
Ar ₁ is a 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, C ₆ ~ C ₆₀ Aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ 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 Arylphosphine group, C ₆ ~ C ₆₀ Mono or diarylphosphine group Pinyl group and C ₆ ~ C _{60 It} is selected from the group consisting of an arylamine group;
The Ar ₁ , R And R _{1 To} R ₇ Alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron Group, arylphosphine group, mono or diarylphosphinyl group and arylamine group are each independently, 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 of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 phosphine group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more selected from the group consisting of an arylamine group, substituted with a plurality of substituents In case they may be the same or different from each other,
When X ₁ is N, the compound represented by Formula 1 is
R ₁ is hydrogen, or R and R ₁ , R and R ₂ , R ₁ and Ar ₁ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and One of R ₇ and R ₇ and Ar ₁ is a compound characterized in that it combines with each other to form the following Chemical Formula 3,
When X ₁ is C(R), the compound represented by Formula 1 is
R and R ₁ , R and R ₂ , R ₁ and Ar ₁ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ and R ₇ and Ar _One of 1 is combined with each other to form a compound characterized in that the formula (3):
[Formula 3]

In the above formula,
The dotted line is the part where the condensation takes place,
X ₂ is selected from the group consisting of C(Ar ₂ )(Ar ₃ ), N(Ar ₄ ), O, S;
R ₁₀ to R ₁₃ are the same as or different from each other, and 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 ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ 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 phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in the, form a condensed ring by combining adjacent tile can do,
Ar _{2 To} Ar _{4 Are} the same as or different from each other, and each independently a 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 ~ C ₆₀ Aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ 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 phosphine group , C ₆ ~ C ₆₀ Mono or diarylphosphinyl group and C ₆ ~ C ₆₀ Selected from the group consisting of an arylamine group,
The R _{10 To} R ₁₃ And Ar _{2 To} Ar ₄ An alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, aryl A boron group, an arylphosphine group, a mono or diarylphosphinyl group and an arylamine group are each independently, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 phosphine group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more selected from the group consisting of an arylamine group, the substituent is In the case of a plurality, they may be the same as or different from each other. The compound according to claim 1, wherein Ar ₁ is a substituent represented by the following formula (2) or a phenyl group:
[Formula 2]

In Formula 2,
* means a moiety bonded to Formula 1;
L is a single bond, or _{is selected from the group consisting of a C 6} ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Y _{1 To} Y _{5 Are} the same as or different from each other, and each independently is N or C(R ₈ ), provided _{that at least one of Y 1 To} Y ₅ is N, and when R ₈ is plural, they are the same or different from each other, ;
R ₈ 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 ₆ ~ C ₄₀ aryl group, Heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ Aryloxy group C ₁ ~ C ₄₀ Alkyloxy group, C ₃ ~ C ₄₀ Cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ Mono or diarylphosphinyl group and C ₆ ~ C _{40 It} is selected from the group consisting of an arylsilyl group, or is _{combined with an adjacent group (eg, L, another adjacent R 8} ) to form a condensed ring can form;
Alkyl group of the R _8, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl 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 of alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ 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 ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ unsubstituted and, when the substituents are plural, they may be the same as or different from each other. delete The compound according to claim 1, wherein Ar ₂ to Ar ₄ are a substituent represented by the following formula (2) or a phenyl group:
[Formula 2]

In Formula 2,
* means a moiety bonded to Formula 1;
L is a single bond, or _{is selected from the group consisting of a C 6} ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Y _{1 To} Y _{5 Are} the same as or different from each other, and each independently is N or C(R ₈ ), provided _{that at least one of Y 1 To} Y ₅ is N, and when R ₈ is plural, they are the same or different from each other, ;
R ₈ 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 ₆ ~ C ₄₀ aryl group, Heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ Aryloxy group C ₁ ~ C ₄₀ Alkyloxy group, C ₃ ~ C ₄₀ Cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₄₀ Arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ Aryl boron group, C ₆ ~ C ₄₀ Arylphosphine group, C ₆ ~ C ₄₀ Mono or diarylphosphinyl group and C ₆ ~ C _{40 It} is selected from the group consisting of an arylsilyl group, or is _{combined with an adjacent group (eg, L, another adjacent R 8} ) to form a condensed ring can form;
Alkyl group of the R _8, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl 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 of alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ 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 ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ unsubstituted and, when the substituents are plural, they may be the same as or different from each other. The compound according to claim 1, characterized in that it is represented by the following Chemical Formulas 4 to 7:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 4 to 7,
X ₁ , X ₂ , R ₁ to R ₇ are as defined in claim 1 , and R ₁₀ to R ₁₃ are as defined in claim 1 . The compound according to claim 2 or 4, wherein the substituent represented by Formula 2 is a substituent represented by any one of the following A-1 to A-15:

In the above A-1 to A-15,
L and R ₈ are each as defined in Formula 2 above,
n is an integer of 0 to 4, and when n is 0, _{it means that hydrogen is not substituted with a substituent R 9} , and when n is an integer of 1 to 4, R ₉ is 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 ~ C ₄₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C _{40 60} aryloxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ mono or diaryl phosphine of C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ P It is selected from the group consisting of a nyl group and a C ₆ ~ C _{40 arylsilyl group, or may be combined with an adjacent group (eg, L, R 8} or other R _9, etc.) to form a condensed ring,
Alkyl group of the R _9, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an 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 of alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ 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 ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₄₀ unsubstituted and, when the substituents are plural, they may be the same as or different from each other. The compound of claim 5, wherein X ₂ is any one of N(Ar ₄ ), O, and S. The compound according to claim 1, wherein at least one of _{R, R 1} to R ₇ , R ₁₀ to R ₁₃ and Ar ₁ to Ar _{4 is a C 6} to C ₄₀ arylamine group. The compound according to claim 1, characterized in that the compound 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 the compound according to claim 1. The organic electroluminescent device according to claim 10, wherein the compound according to claim 1 is used as a phosphorescent host of the light emitting layer. The organic electroluminescent device according to claim 10, wherein the compound according to claim 1 is used as a hole transport layer.