KR102283298B1 - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent light emitting ability and to 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 azepine-based compound having excellent hole injection and transport ability, light emitting ability, and the like, and luminous efficiency by including the same in one or more organic material layers; It relates to an organic electroluminescent device having 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.

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

two of R ₁ and R ₂ , R ₃ and R _{4 ,} and R ₅ and R ₆ are bonded to each other to form a condensed ring with Formula 2 below, and the other is bonded to each other to form a condensation with Formula 3 below;

[Formula 2]

[Formula 3]

In Formula 2 and Formula 3,

The dotted line is the portion where the condensation takes place;

X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ );

Y ₁ to Y ₈ are each independently selected from N or C(R ₇ );

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 having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, 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 Aryl phosphine group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, each adjacent R ₃ is bonded to each other condensed aromatic may form a ring or a condensed heteroaromatic ring,

Ar _{1 To} Ar ₅ 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, heterocyclo having 3 to 40 nuclear atoms Alkyl group, 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 It is selected from the group consisting of a diaryl phosphinyl group and a C ₆ ~ C _{60 arylamine group,}

R ₇ , Ar _{1 To} Ar ₅ Alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, aryl A phosphine 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, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ It may be substituted with one or more selected from the group consisting of an aryl phosphine group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C _{60 arylamine group.} When substituted with a plurality of substituents, 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 at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

In the present invention, "aryl" refers to 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'O-, 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.

1. Novel Organic Compounds

The compound of the present invention is a 5-membered heteroaromatic ring moiety, indene moiety, or indole moiety in which benzene is condensed to benzoazepine, benzoxepin, benzothiepin, benzoxilepine, or benzoannulene. It is characterized in that an indole moiety is condensed to form a basic skeleton, and is represented by Formula 1 below:

[Formula 1]

In Formula 1,

two of R ₁ and R ₂ , R ₃ and R _{4 ,} and R ₅ and R ₆ are bonded to each other to form a condensed ring with Formula 2 below, and the other is bonded to each other to form a condensation with Formula 3 below;

[Formula 2]

[Formula 3]

In Formula 2 and Formula 3,

The dotted line is the portion where the condensation takes place;

X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ );

Y ₁ to Y ₈ are each independently selected from N or C(R ₇ );

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 having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, 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 Aryl phosphine group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, each adjacent R ₃ is bonded to each other condensed aromatic may form a ring or a condensed heteroaromatic ring,

Ar _{1 To} Ar ₅ 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, heterocyclo having 3 to 40 nuclear atoms Alkyl group, 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 It is selected from the group consisting of a diaryl phosphinyl group and a C ₆ ~ C _{60 arylamine group,}

R ₇ , Ar _{1 To} Ar ₅ Alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, aryl A phosphine 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, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ It may be substituted with one or more selected from the group consisting of an aryl phosphine group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C _{60 arylamine group.} When substituted with a plurality of substituents, they may be the same as or different from each other.

Since the compound represented by Formula 1 has a higher molecular weight than the conventional organic EL device material [eg, 4,4-dicarbazolybiphenyl (hereinafter, referred to as 'CBP')], the glass transition temperature is high, and thus the thermal stability is excellent. However, it has excellent carrier transport ability, light emitting ability, and the like. Therefore, when the organic electroluminescent device contains the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device can be improved.

In general, in the phosphorescent light emitting layer of an organic electroluminescent device, the triplet energy gap of the host material should be higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host has higher energy than the lowest emission state of the dopant, phosphorescence efficiency may be improved. In the compound of Formula 1, a specific substituent is introduced into the basic skeleton in which the indole derivative having a high triplet energy and a wide singlet energy level and a high triplet energy level is condensed, so that the energy level can be adjusted higher than that of the dopant. Therefore, it can be used as a host material.

In addition, since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the excitons generated in the emission layer from diffusing into the electron transport layer or the hole transport layer adjacent to the emission layer. Therefore, when an organic material layer (hereinafter, referred to as 'emission auxiliary layer') is formed between the hole transport layer and the light emitting layer using the compound of Formula 1, the diffusion of excitons is prevented by the compound, so that the first exciton diffusion Unlike the conventional organic electroluminescent device that does not include a barrier layer, the number of excitons contributing to light emission in the light emitting layer is substantially increased, so that the light emitting efficiency of the device can be improved. In addition, even when an organic material layer (hereinafter, referred to as a 'lifetime improvement layer') is formed between the light emitting layer and the electron transport layer using the compound of Formula 1, the diffusion of excitons is prevented by the compound of Formula 1, so that the organic electric field Durability and stability of the light emitting device may be improved, and thus the half-life of the device may be effectively increased. As such, the compound represented by Formula 1 may be used as a material for a light emitting auxiliary layer or a material for a life improvement layer other than the host of the light emitting layer.

In addition, the compound of Formula 1 may control the HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, and thus may have a wide band gap and high carrier transport properties. For example, in the compound, when an electron withdrawing group (EWG) having high electron absorption such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) is bonded to the basic skeleton, the entire molecule is Since it has a bipolar characteristic, it is possible to increase the bonding force between holes and electrons. As such, since the compound of Formula 1 in which EWG is introduced into the basic skeleton has excellent carrier transport and light emitting properties, in addition to the light emitting layer material of the organic electroluminescent device, it is also used as an electron injection / transport layer material, or a life improvement layer material. can be used On the other hand, when the compound of Formula 1 is coupled to an electron donor group (EDG) having a large electron donor, such as an arylamine group, a carbazole group, a terphenyl group, or a triphenylene group, to the basic skeleton, hole injection and transport are smooth In addition to the material for the light emitting layer, it can be usefully used as a material for a hole injection/transport layer or a light emitting auxiliary layer.

As such, the compound represented by Chemical Formula 1 can improve the light emitting characteristics of the organic electroluminescent device and, at the same time, improve hole injection/transport ability, electron injection/transport ability, luminous efficiency, driving voltage, lifespan characteristics, etc. . Accordingly, the compound of Formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and/or red phosphorescent host material), an electron transport/injection layer material, and a hole transport/injection layer It can be used as a material, a light emitting auxiliary layer material, a life improving layer material, more preferably a light emitting layer material, an electron injection layer material, a light emitting auxiliary layer material, or a life improving layer material.

In addition, in the compound of Formula 1, various substituents, in particular, an aryl group and/or a heteroaryl group are introduced into the basic skeleton to significantly increase the molecular weight of the compound, so that the glass transition temperature can be improved. It may have a higher thermal stability than the material (eg, CBP). In addition, the compound represented by Formula 1 is effective in inhibiting crystallization of the organic material layer. Accordingly, the performance and lifespan characteristics of the organic electroluminescent device including the compound of Formula 1 according to the present invention can be greatly improved, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can also be maximized.

According to one embodiment of the present invention, the compound of the present invention is _{two of R 1} and R 2 , R ₃ and R ₄ and R ₅ and R ₆ are bonded to each other to form N, O, S, It may form a condensed heteroaromatic ring or condensed aromatic ring containing at least one of Si, and the other one is combined with each other to form a condensed heteroaromatic ring or condensed aromatic ring containing at least one N represented by the following formula (3) can

According to one embodiment of the present invention, R ₁ and R ₂ , R ₃ and R ₄ are combined to form condensed indene, condensed indole, condensed benzothiophene, condensed benzofuran, condensed benzosilol, and the like, and R ₅ and R ₆ may combine to form benzene, pyridine, pyrimidine, and the like.

According to one embodiment of the present invention, R ₁ and R ₂ , R ₅ and R ₆ are combined to form condensed indene, condensed indole, condensed benzothiophene, condensed benzofuran, condensed benzosilol, and the like, and R ₃ and R ₄ may combine to form benzene, pyridine, pyrimidine, and the like.

More specifically, the compound of the present invention may be specifically represented by the following Chemical Formulas 4 to 10.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 4 to 10,

X ₁ , X ₂ and Y ₁ to Y ₈ are as defined in Formulas 1 and 2.

According to one embodiment of the present invention, in Formulas 4 to 10, X ₁ and X ₂ are each independently O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ ) (Ar ₅ ) It is selected from the group consisting of _{, and is preferably O, S, N(Ar 1} ), and at least one of these is preferably N(Ar ₁ ).

According to one embodiment of the present invention, in Formulas 4 to 10, Y ₁ to Y ₈ are each independently selected from N or C(R ₇ ), all of which are C(R ₇ ), or one of them is preferably N do.

The compound of the present invention may be specifically selected from the group consisting of compounds represented by the following Chemical Formulas 1-1 to 1-21, but is not limited thereto.

In Formulas 1-1 to 1-21,

Each of Y ₁ to Y ₈ and Ar ₁ to Ar ₅ are the same or different, and are as defined in Formulas 1 to 3.

In Formulas 1-1 to 1-21, at least one of _{R 7} , and Ar ₁ to Ar _{5 except for forming a condensation is a C 1} to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, the number of nuclear atoms 5 to 60 heteroaryl groups and C ₆ to C ₆₀ selected from the group consisting of an arylamine group, and the alkyl group, aryl group, heteroaryl group, and arylamine group are each independently, deuterium, halogen, cyano group, C ₁ ~ It may be substituted with one or more selected from the group consisting of C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, and C ₆ ~ C _{60 arylamine group.} 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, at least one of R 7} , and Ar ₁ to Ar ₅ except for forming a condensation in Chemical Formulas 1 to 3 may be a substituent represented by the following Chemical Formula 11 or a phenyl group.

[Formula 11]

In the above formula (11),

* means a moiety bonded to Formula 1;

L ₁ 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, a biphenylene group, a carbazolyl group can;

Z ₁ to Z ₅ are the same or different from each other, and each independently is N or C(R ₁₁ ), provided _{that at least one of Z 1} to Z ₅ is N, and when R ₁₁ is plural, they are the same or different from each other, ;

R ₁₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C 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, other adjacent R 11} ) to form a condensed ring can form;

Alkyl group of the R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, 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 11 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 ₁ and R ₁₁ are each as defined in Formula 5 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 12} , and when n is an integer of 1 to 4, R ₁₂ 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 1} , R ₁₁ or other R _{12 ,} etc.) to form a condensed ring,

Alkyl group of the R _12, 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.

_{According to a preferred embodiment of the present invention, at least one of R 7} , and Ar ₁ to Ar ₅ except for forming a condensation in Chemical Formulas 1 to 3 may be a substituent represented by the following Chemical Formula 12.

[Formula 12]

In the above formula (12),

* means a moiety bonded to Formula 1;

L ₂ 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, a biphenylene group, a carbazolyl group can;

R ₁₃ and R ₁₄ are each independently selected from _{the group consisting of a C 1} ~ C ₄₀ alkyl group, a C ₆ ~ C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group or R ₁₃ and R ₁₄ may combine to form a condensed ring;

The _{alkyl group, aryl group, heteroaryl group and arylamine group of R 13} and R ₁₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group having 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 one substituent at least one selected from the group consisting of C ₆ ~ with an aryl silyl group of C ₄₀ of the When substituted or unsubstituted, and the above substituents are plural, they may be the same as or different from each other.

Chemical Formula 1 of the present invention is the following compound, which may be more specifically represented by the following structure, 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 there is. 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 at the interface between the electrode and the organic material layer.

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 DIA-1

<Step 1> Synthesis of N-(1H-indol-2-yl)-N-phenyl-1H-indol-2-amine

2-bromo-1H-indole (12.75 g, 80.0 mmol) with aniline (3.72 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P(t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, column chromatography was used to obtain the target compound, N-(1H-indol-2-yl)-N-phenyl-1H-indol-2-amine (7.24 g, yield 56%). .

¹ H-NMR: δ6.65 (d, 2H), 6.85 (m, 7H), 7.18 (t, 2H), 7.52 (d, 2H), 7.64 (d, 2H), 11.9 (s, 2H)

<Step 2> Synthesis of 3-iodo-N-(3-iodo-1H-indol-2-yl)-N-phenyl-1H-indol-2-amine

After dissolving N-(1H-indol-2-yl)-N-phenyl-1H-indol-2-amine (6.47 g, 20.0 mmol) and KOH (2.81 g, 50.0 mmol) in 80 ml DMF, at room temperature for 20 minutes stirred. _{I 2} (5.07 g, 20.0 mmol) dissolved in DMF was added and stirred for 1 hour.

After completion of the reaction, 100 ml of ice water is added and the solid is extracted. After removing the solvent of the filtered organic layer using column chromatography, the target 3-iodo-N-(3-iodo-1H-indol-2-yl)-N-phenyl-1H-indol-2-amine (10.6 g, yield 92%) was obtained.

¹ H-NMR: δ6.64 (d, 2H), 6.93 (t, 5H), 7.18 (t, 2H), 7.64 (d, 2H), 7.92 (d, 2H), 11.2 (s, 2H)

<Step 3> Synthesis of 10-phenyl-10,11-dihydro-9H-benzo [4,5] azepino [2,3-b: 7,6-b'] diindole

3-iodo-N-(3-iodo-1H-indol-2-yl)-N-phenyl-1H-indol-2-amine (28.7 g, 50.0 mmol), 1,2-bis(3-iodo-1H-indol-2-yl) under a nitrogen stream 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (16.5 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1, 4-Dioxane/H ₂ O (120 ml/40 ml) was mixed, and then Pd(PPh ₃ ) ₄ (2.88 g, 5 mol%) was added and stirred at 120° C. for 12 hours.

After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography to 10-phenyl-10,11-dihydro-9H-benzo [4,5] azepino [2,3-b: 7,6-b'] diindole (10.3 g, yield 52%) was obtained.

¹ H-NMR: δ6.58 (d, 2H), 6.79 (t, 1H), 7.15 (t, 6H), 7.52 (m, 6H), 7.82 (d, 2H), 11.2 (s, 2H)

<Step 4> Synthesis of DIA-1

10-phenyl-10,11-dihydro-9H-benzo [4,5] azepino [2,3-b: 7,6-b '] diindole (23.8 g, 60.0 mmol) and iodo under a nitrogen stream Benzene (6.12 g, 30.0 mmol), Cu powder (0.45 g, 15.0 mmol), K ₂ CO ₃ (12.4 g, 90.0 mmol), and nitrobenzene (200 ml) were mixed and stirred at 250° 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 from the organic layer from which water was removed, it was purified by column chromatography to obtain DIA-1 (10.2 g, yield 72%).

¹ H-NMR: δ6.63 (d, 2H), 6.78 (t, 1H), 7.06 (t, 2H), 7.19 (t, 2H), 7.43 (m, 11H), 7.68 (d, 1H), 7.84 (d, 2H), 8.15 (d, 1H), 11.2 (s, 1H)

[Preparation Example 2] Synthesis of D IA-2 and DIA-3

<Step 1> Synthesis of N-phenyl-1H-indol-2-amine

2-bromo-1H-indole (12.75 g, 40.0 mmol) with aniline (3.72 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P(t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, the target compound, N-phenyl-1H-indol-2-amine (5.33 g, yield 64%) was obtained by column chromatography.

¹ H-NMR: δ 4.01 (s, 1H), 6.83 (m, 4H), 7.18 (t, 2H), 7.61 (d, 4H), 11.9 (s, 1H)

<Step 2> Synthesis of N-(2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-2-amine

N-phenyl-1H-indol-2-amine (8.33 g, 40.0 mmol) with 3-bromo-2-chloro-1H-indole (9.22 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P(t-Bu) ₃ (0.80 g, 4.0 mmol), and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer using column chromatography, the target compound, N-(2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-2-amine (5.29 g, yield 37) %) was obtained.

¹ H-NMR: δ6.57 (m, 3H), 6.86 (m, 5H), 7.18 (t, 2H), 7.41 (t, 1H), 7.52 (d, 1H), 7.64 (d, 2H), 11.9 (s, 2H)

<Step 3> Synthesis of 3-chloro-N- (2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-2-amine

After dissolving N-(2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-2-amine (5.68 g, 20.0 mmol) and KOH (2.81 g, 50.0 mmol) in 80 ml DMF, room temperature was stirred for 20 min. _{Cl 2} (1.42 g, 20.0 mmol) dissolved in DMF was added and stirred for 1 hour.

After completion of the reaction, 100 ml of ice water is added to extract the solid. After removing the solvent of the filtered organic layer, the desired 3-chloro-N-(2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-2-amine (6.67 g, yield 85%) was obtained.

¹ H-NMR: δ6.63 (d, 3H), 6.78 (t, 1H), 6.97 (t, 2H), 7.19 (t, 3H), 7.39 (d, 1H), 7.63 (d, 3H), 11.8 (s, 2H)

<Step 4> Synthesis of 10-phenyl-10,15-dihydro-9H-benzo [4,5] azepino [2,3-b: 6,7-b'] diindole

3-chloro-N- (2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-2-amine (19.6 g, 50.0 mmol), 1,2-bis (4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (14.7 g, 50.0 mmol), Cs ₂ CO ₃ (3.26 g, 10.0 mmol), X-phos ( 0.56 g, 5 mmol), Pd(OAc) ₂ (2.88 g, 5 mol%) and 1,4-dioxane/H ₂ O (120 ml/40 ml) were mixed and then stirred at 120° C. for 12 hours. .

After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent from the obtained organic layer, it was purified by column chromatography to 10-phenyl-10,15-dihydro-9H-benzo [4,5] azepino [2,3-b: 6,7-b'] diindole (11.9 g, yield 75%) was obtained.

¹ H-NMR: δ6.52 (m, 3H), 6.78 (t, 1H), 7.11 (t, 5H), 7.48 (m, 5H), 7.64 (d, 1H), 7.84 (d, 2H), 11.2 (s, 1H), 11.4 (s, 1H)

<Step 5> Synthesis of DIA-2 and DIA-3

10-phenyl-10,15-dihydro-9H-benzo [4,5] azepino [2,3-b: 6,7-b '] diindole (23.8 g, 60.0 mmol) and iodo under a nitrogen stream Benzene (6.12 g, 30.0 mmol), Cu powder (0.45 g, 15.0 mmol), K ₂ CO ₃ (12.4 g, 90.0 mmol), and nitrobenzene (200 ml) were mixed and stirred at 250° 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 from the organic layer from which water was removed, it was purified by column chromatography to obtain DIA-2 (5.96 g, yield 42%) and DIA-3 (5.96 g, yield 42%).

DIA-2_ ¹ H-NMR: δ6.59 (m, 3H), 6.78 (t, 1H), 6.97 (t, 1H), 7.18 (t, 2H), 7.53 (m, 12H), 7.83 (d, 2H) ), 8.15 (d, 1H), 11.2 (s, 1H)

DIA-3_ ¹ H-NMR: δ6.62 (d, 2H), 6.78 (t, 1H), 7.07 (t, 2H), 7.47 (m, 14H), 7.87 (d, 3H), 11.8 (s, 1H) )

[Preparation Example 3] Synthesis of DIA-3

<Step 1> Synthesis of 2-chloro-N-(2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-3-amine

3-Bromo-2-chloro-1H-indole (18.4 g, 80.0 mmol) with aniline (3.73 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P(t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound, 2-chloro-N-(2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-3-amine (9.73 g, yield 62%) was obtained.

¹ H-NMR: δ6.57 (m, 4H), 6.78 (t, 1H), 6.97 (t, 2H), 7.18 (t, 2H), 7.41 (d, 2H), 7.65 (d, 2H), 11.8 (s, 2H)

<Step 2> Synthesis of 10-phenyl-10,15-dihydro-5H-benzo [4,5] azepino [3,2-b: 6,7-b'] diindole

2-chloro-N- (2-chloro-1H-indol-3-yl)-N-phenyl-1H-indol-3-amine (19.6 g, 50.0 mmol), 1,2-bis (4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (16.5 g, 50.0 mmol), Cs ₂ CO ₃ (3.26 g, 10.0 mmol), X-phos ( 0.56 g, 5 mmol), Pd(OAc) ₂ (2.88 g, 5 mol%) and 1,4-dioxane/H ₂ O (120 ml/40 ml) were mixed and then stirred at 120° C. for 12 hours. .

After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography to 10-phenyl-10,15-dihydro-5H-benzo [4,5] azepino [3,2-b: 6,7-b'] diindole (11.3 g, yield 57%) was obtained.

¹ H-NMR: δ6.52 (d, 4H), 6.78 (t, 1H), 6.97 (t, 2H), 7.18 (t, 2H), 7.44 (m, 4H), 7.65 (d, 2H), 7.84 (d, 2H), 11.2 (s, 2H)

<Step 3> Synthesis of DIA-3

10-phenyl-10,15-dihydro-5H-benzo [4,5] azepino [3,2-b: 6,7-b'] diindole (23.8 g, 60.0 mmol) and iodo under a nitrogen stream Benzene (6.12 g, 30.0 mmol), Cu powder (0.45 g, 15.0 mmol), K ₂ CO ₃ (12.4 g, 90.0 mmol), and nitrobenzene (200 ml) were mixed and stirred at 250° 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 from the organic layer from which water was removed, it was purified by column chromatography to obtain DIA-4 (10.8 g, yield 76%).

¹ H-NMR: δ6.62 (m, 3H), 6.78 (t, 1H), 6.97 (t, 1H), 7.59 (m, 14H), 7.89 (d, 3H), 11.2 (s, 1H)

[Synthesis Example 1] Synthesis of A-10

DIA-1 (4.73 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol) ), P(t-Bu) ₃ (0.40 g, 2.0 mmol), and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound A-10 (6.06 g, yield 86%) was obtained by column chromatography.

MS [M+1] ⁺ 705

[Synthesis Example 2] Synthesis of A-12

Synthesis Example 1, except that 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same method was followed to obtain the target compound A-12 (5.91 g, yield 84%).

MS [M+1] ⁺ 704

[Synthesis Example 3] Synthesis of A-13

2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol ) was performed in the same manner as in Synthesis Example 1, except that the target compound A-13 (6.79 g, yield 87%) was obtained.

MS [M+1] ⁺ 781

[Synthesis Example 4] Synthesis of A-15

Except for using 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) in place of 2-chloro-4,6-diphenyl-1,3,5-triazine was performed in the same manner as in Synthesis Example 1 to obtain the target compound A-15 (6.39 g, yield 82%).

MS [M+1] ⁺ 780

[Synthesis Example 5] Synthesis of A-30

N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ,1'-biphenyl]-4-amine (6.69 g, 10.00 mmol) was carried out in the same manner as in Synthesis Example 1, except that the target compound A-30 (5.80 g, yield 77%) was obtained.

MS [M+1] ⁺ 870

[Synthesis Example 6] Synthesis of A-33

The same method as in Synthesis Example 1, except that 2-bromo-4-phenylquinazoline (2.85 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the target compound A-33 (5.42 g, yield 80%).

MS [M+1] ⁺ 678

[Synthesis Example 7] Synthesis of A-34

Use 2-bromo-4-(4-(naphthalen-1-yl)phenyl)quinazoline (4.11 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine In the same manner as in Synthesis Example 1, except that the target compound A-34 (5.27 g, yield 82%) was obtained.

MS [M+1] ⁺ 677

[Synthesis Example 8] Synthesis of A-37

The same method as in Synthesis Example 1, except that 8-(4-bromophenyl)quinoline (2.84 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the target compound A-37 (6.59 g, yield 78%).

MS [M+1] ⁺ 804

[Synthesis Example 9] Synthesis of A-43

2-Chloro-4,6-diphenyl-1,3,5-triazine instead of N-([1,1'-biphenyl]-4-yl)-N-(4'-bromo-[1, 1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was carried out in the same manner as in Synthesis Example 1, except that the Compound A-43 (7.88 g, yield 80%) was obtained.

MS [M+1] ⁺ 986

[Synthesis Example 10] Synthesis of B-10

DIA-2 (4.73 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol) ), P(t-Bu) ₃ (0.40 g, 2.0 mmol), and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound B-10 (5.77 g, yield 82%) was obtained by column chromatography.

MS [M+1] ⁺ 705

[Synthesis Example 11] Synthesis of B-12

Synthesis Example 10 and 2-chloro-4,6-diphenyl-1,3,5-triazine except for using 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) instead of triazine The same method was followed to obtain the target compound B-12 (5.56 g, yield 79%).

MS [M+1] ⁺ 704

[Synthesis Example 12] Synthesis of B-13

2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol ) was performed in the same manner as in Synthesis Example 10, except that the target compound B-13 (6.55 g, yield 84%) was obtained.

MS [M+1] ⁺ 781

[Synthesis Example 13] Synthesis of B-15

Except for using 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) in place of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out in the same manner as in Synthesis Example 10 to obtain the target compound B-15 (6.62 g, yield 85%).

MS [M+1] ⁺ 780

[Synthesis Example 14] Synthesis of B-30

N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ,1'-biphenyl]-4-amine (4.76 g, 10.00 mmol) was performed in the same manner as in Synthesis Example 10, except that the target compound B-30 (6.60 g, yield 76%) was obtained.

MS [M+1] ⁺ 870

[Synthesis Example 15] Synthesis of B-33

The same method as in Synthesis Example 10 except that 2-bromo-4-phenylquinazoline (2.85 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the target compound B-33 (5.42 g, yield 80%).

MS [M+1] ⁺ 678

[Synthesis Example 16] Synthesis of B-34

Use 2-bromo-4-(4-(naphthalen-1-yl)phenyl)quinazoline (4.11 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine In the same manner as in Synthesis Example 10, except that the target compound B-34 (5.07 g, yield 82%) was obtained.

MS [M+1] ⁺ 677

[Synthesis Example 17] Synthesis of B-37

The same method as in Synthesis Example 10, except that 8-(4-bromophenyl)quinoline (2.84 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the target compound B-37 (6.59 g, yield 75%).

MS [M+1] ⁺ 804

[Synthesis Example 18] Synthesis of B-43

2-Chloro-4,6-diphenyl-1,3,5-triazine instead of N-([1,1'-biphenyl]-4-yl)-N-(4'-bromo-[1, 1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was carried out in the same manner as in Synthesis Example 10, except that the Compound B-43 (7.09 g, yield 72%) was obtained.

MS [M+1] ⁺ 986

[Synthesis Example 19] Synthesis of C-10

DIA-3 (4.73 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol) ), P(t-Bu) ₃ (0.40 g, 2.0 mmol), and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound C-10 (5.28 g, yield 75%) was obtained by column chromatography.

MS [M+1] ⁺ 705

[Synthesis Example 20] Synthesis of C-12

Synthesis Example 19, except that 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same method was followed to obtain the target compound C-12 (5.13 g, yield 73%).

MS [M+1] ⁺ 704

[Synthesis Example 21] Synthesis of C-13

2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol ) was carried out in the same manner as in Synthesis Example 19, except that the target compound C-13 (6.16 g, yield 79%) was obtained.

MS [M+1] ⁺ 781

[Synthesis Example 22] Synthesis of C-15

Except for using 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) in place of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out in the same manner as in Synthesis Example 19 to obtain the target compound C-15 (5.92 g, yield 76%).

MS [M+1] ⁺ 780

[Synthesis Example 23] Synthesis of C-30

N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ,1'-biphenyl]-4-amine (4.76 g, 10.00 mmol) was performed in the same manner as in Synthesis Example 19, except that the target compound C-30 (6.08 g, yield 70%) was obtained.

MS [M+1] ⁺ 870

[Synthesis Example 24] Synthesis of C-33

The same method as in Synthesis Example 19, except that 2-bromo-4-phenylquinazoline (2.85 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the target compound C-33 (4.60 g, yield 68%).

MS [M+1] ⁺ 678

[Synthesis Example 25] Synthesis of C-34

Use 2-bromo-4-(4-(naphthalen-1-yl)phenyl)quinazoline (4.11 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine In the same manner as in Synthesis Example 19, except that the target compound C-34 (5.00 g, yield 74%) was obtained.

MS [M+1] ⁺ 677

[Synthesis Example 26] Synthesis of C-37

The same method as in Synthesis Example 19, except that 8-(4-bromophenyl)quinoline (2.84 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the target compound C-37 (5.78 g, yield 72%).

MS [M+1] ⁺ 804

[Synthesis Example 27] Synthesis of C-43

2-Chloro-4,6-diphenyl-1,3,5-triazine instead of N-([1,1'-biphenyl]-4-yl)-N-(4'-bromo-[1, 1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was carried out in the same manner as in Synthesis Example 19, except that the objective Compound C-43 (7.29 g, yield 74%) was obtained.

MS [M+1] ⁺ 986

[Synthesis Example 28] Synthesis of D-10

DIA-4 (4.73 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol) ), P(t-Bu) ₃ (0.40 g, 2.0 mmol), and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110° C. for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound D-10 (5.56 g, yield 79%) was obtained by column chromatography.

MS [M+1] ⁺ 705

[Synthesis Example 29] Synthesis of D-12

Synthesis Example 28, except that 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same method was followed to obtain the target compound D-12 (5.27 g, yield 75%).

MS [M+1] ⁺ 704

[Synthesis Example 30] Synthesis of D-13

2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol ) was carried out in the same manner as in Synthesis Example 28 except that the target compound D-13 (6.48 g, yield 83%) was obtained.

MS [M+1] ⁺ 781

[Synthesis Example 31] Synthesis of D-15

Except for using 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) in place of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out in the same manner as in Synthesis Example 28 to obtain the target compound D-15 (6.55 g, yield 84%).

MS [M+1] ⁺ 780

[Synthesis Example 32] Synthesis of D-30

N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ,1'-biphenyl]-4-amine (4.76 g, 10.00 mmol) was performed in the same manner as in Synthesis Example 28, except that the target compound D-30 (6.77 g, yield 78%) was obtained.

MS [M+1] ⁺ 870

[Synthesis Example 33] Synthesis of D-33

The same method as in Synthesis Example 28, except that 2-bromo-4-phenylquinazoline (2.85 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the target compound D-33 (5.01 g, yield 74%).

MS [M+1] ⁺ 678

[Synthesis Example 34] Synthesis of D-34

Use 2-bromo-4-(4-(naphthalen-1-yl)phenyl)quinazoline (4.11 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine In the same manner as in Synthesis Example 28, except that the target compound D-34 (5.54 g, yield 82%) was obtained.

MS [M+1] ⁺ 677

[Synthesis Example 35] Synthesis of D-37

The same method as in Synthesis Example 28, except that 8-(4-bromophenyl)quinoline (2.84 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the target compound D-37 (6.27 g, yield 78%).

MS [M+1] ⁺ 804

[Synthesis Example 36] Synthesis of D-43

2-Chloro-4,6-diphenyl-1,3,5-triazine instead of N-([1,1'-biphenyl]-4-yl)-N-(4'-bromo-[1, 1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was carried out in the same manner as in Synthesis Example 28, except that the Compound D-43 (7.38 g, yield 75%) was obtained.

MS [M+1] ⁺ 986

[Examples 1 to 16] Preparation of green organic EL device

Compounds A-10 to D-15 synthesized in Synthesis Examples 1-31 were 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)/ each compound of A-10 to D-15 + 10% Ir(ppy) ₃ (30 nm)/BCP (10 nm)/Alq on the prepared ITO transparent electrode ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate an organic EL device.

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 A-10 as a light emitting host material when the light emitting layer was formed.

[Evaluation example]

For each of the green organic EL devices manufactured in Examples 1 to 16 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 A-10 6.88 517 40.2 Example 2 A-12 6.83 518 40.3 Example 3 A-13 6.79 517 41.2 Example 4 A-15 6.83 516 41.6 Example 5 B-10 6.77 518 40.2 Example 6 B-12 6.87 518 41.6 Example 7 B-13 6.79 517 40.3 Example 8 B-15 6.84 518 40.7 Example 9 C-10 6.88 517 41.5 Example 10 C-12 6.73 517 41.6 Example 11 C-13 6.89 518 41.2 Example 12 C-15 6.84 518 40.8 Example 13 D-10 6.83 516 41.3 Example 14 D-12 6.77 518 40.5 Example 15 D-13 6.82 517 41.2 Example 16 D-15 6.89 518 40.6 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compounds (A-10 to D-15) according to the present invention were used as a light emitting layer of a green organic EL device (Example 1-16), a green organic EL device using conventional CBP (comparative It can be seen that compared to Example 1), it shows better performance in terms of efficiency and driving voltage.

[Examples 17 to 28] Preparation 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

m-MTDATA (60 nm)/TCTA (80 nm)/ Compounds of A-33 to D-37 + 10% (piq) ₂ Ir(acac) (30 nm)/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]

A red organic electroluminescent device was manufactured in the same manner as in Example 17, except that CBP was used instead of the compound of Synthesis Example 6 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 17 to 28 and Comparative Example 2 are as follows.

[Evaluation example]

For each organic electroluminescent device manufactured in Examples 17 to 28 and Comparative Example 2, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below.

Sample host Driving voltage (V) Current efficiency (cd/A) Example 17 A-33 4.85 12.5 Example 18 A-34 4.98 13.3 Example 19 A-37 4.89 12.9 Example 20 B-33 4.93 13.4 Example 21 B-34 4.92 13.3 Example 22 B-37 4.89 12.8 Example 23 C-33 4.92 12.8 Example 24 C-34 4.88 12.5 Example 25 C-37 4.81 13.4 Example 26 D-33 4.98 13.2 Example 27 D-34 4.89 13.9 Example 28 D-37 4.93 12.9 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention was used as a material of the light emitting layer of a red organic electroluminescent device (Examples 17-28), a red organic electroluminescent device using conventional CBP as a material of the light emitting layer (Comparative Example) 2), it can be seen that the performance is excellent in terms of efficiency and driving voltage.

[Example 29] Preparation of organic EL device

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

m-MTDATA (60 nm) / Compound A-30 (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq3 (30) synthesized in Synthesis Example 5 on the ITO transparent electrode prepared as described above nm)/LiF (1 nm)/Al (200 nm) in order to manufacture an organic EL device.

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.

[Examples 30 to 36] Preparation of organic EL devices

An organic EL device was fabricated in the same manner as in Example 29, except for using each synthesized compound A-43 to D-43 instead of compound A-30 used as a hole transport layer material when forming the hole transport layer in Example 29. prepared.

[Comparative Example 3] Fabrication of organic EL device

An organic EL device was manufactured in the same manner as in Example 29, except that NPB was used as a hole transport layer material instead of Compound A-30 used as a hole transport layer material when the hole transport layer was formed in Example 29. The structure of the NPB used is as follows.

[Evaluation Example 3]

The driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured for the organic EL devices prepared in Examples 29 to 36 and Comparative Example 3, respectively, and the results are shown in Table 1 below.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example 29 A-30 4.8 21.4 Example 30 A-43 4.8 21.6 Example 31 B-30 4.7 21.7 Example 32 B-43 5.0 22.3 Example 33 C-30 5.1 20.7 Example 34 C-43 4.8 20.9 Example 35 D-30 4.9 20.4 Example 36 D-43 4.7 21.5 Comparative Example 3 NPB 5.2 18.1

As shown in Table 3, the organic EL devices (organic EL devices prepared in Examples 29 to 36, respectively) using the compounds (A-30 to L-48) according to the present invention as a hole transport layer were prepared using conventional NPB. It was found that the organic EL device (the organic EL device of Comparative Example 3) showed better performance in terms of current efficiency and driving voltage.

Claims (17)

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

In Formula 1,
_{Two of} R ₁ and R 2 , R ₃ and R _{4 ,} and R ₅ and R ₆ are condensed with each other to form a condensed ring represented by the following formula (2), and the other one is condensed with each other to form a condensed ring represented by the following formula (3) to form;
[Formula 2]

[Formula 3]

In Formula 2 and Formula 3,
The dotted line is the portion where the condensation takes place;
X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ) and Si(Ar ₄ )(Ar ₅ );
Y _{1 To} Y ₈ are each independently selected from N or C (R ₇ ),
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 having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, 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 Aryl phosphine group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, each adjacent R ₇ is bonded to each other condensed aromatic may form a ring or a condensed heteroaromatic ring,
Ar _{1 To} Ar ₅ 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, heterocyclo having 3 to 40 nuclear atoms Alkyl group, 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 It is selected from the group consisting of a diaryl phosphinyl group and a C ₆ ~ C _{60 arylamine group,}
R ₇ , and Ar _{1 To} Ar ₅ 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, an arylboron group, Arylphosphine group, mono or diaryl phosphinyl 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 of a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ of Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ may be substituted with one or more selected from the group consisting of an aryl phosphine group, a C ₆ to C ₆₀ mono or diaryl phosphinyl group, and a C ₆ to C ₆₀ arylamine group, and when substituted with a plurality of substituents, they are each other may be the same or different. The compound according to claim 1, characterized in that it is represented by the following Chemical Formulas 4 to 10.
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 4 to 10,
X ₁ , X ₂ and Y ₁ to Y ₈ are as defined in claim 1. The compound according to claim 1, wherein at least one of _{X 1} and X _{2 is N(Ar 1} ). The compound according to claim 1 or 2, wherein Y ₁ to Y ₈ are each independently selected from N or C(R ₇ ), all of which are C(R ₇ ), or one of them is N. The compound according to claim 1, characterized in that it is represented by the following Chemical Formulas 1-1 to 1-21.

In Formulas 1-1 to 1-21,
Each of Y ₁ to Y ₈ and Ar ₁ is the same or different, as defined in claim 1. According to claim 1, except for forming a condensation R ₇ , and Ar _{1 To} Ar ₅ At least one of C ₁ ~ C ₄₀ Alkyl group, C ₆ ~ C ₆₀ Aryl group, 5 to 60 nuclear atoms hetero An aryl group and a C ₆ ~ C ₆₀ A compound, characterized in that selected from the group consisting of an arylamine group. 7. The method of claim 6, wherein the alkyl group, aryl group, heteroaryl group, and arylamine group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, number of nuclear atoms 5 to 60 heteroaryl groups, C ₆ to C ₆₀ may be substituted with one or more selected from the group consisting of arylamine groups, and when substituted with a plurality of substituents, these may be the same or different from each other. .
The compound according to claim 1, wherein _{at least one of R 7} , and Ar ₁ to Ar ₅ except for forming a condensation is a substituent represented by the following formula (11).
[Formula 11]

In the above formula (11),
* means a moiety bonded to Formula 1;
L ₁ 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,
Z ₁ to Z ₅ are the same or different from each other, and each independently is N or C(R ₁₁ ), provided _{that at least one of Z 1} to Z ₅ is N, and when R ₁₁ is plural, they are the same or different from each other, ;
R ₁₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C 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} may be selected from the group consisting of an arylsilyl group, or combined with an adjacent group to form a condensed ring;
Alkyl group of the R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, 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 8, wherein Chemical Formula 5 is a substituent represented by the following Chemical Formulas A-1 to A-15.

In the above A-1 to A-15,
L ₁ and R ₁₁ are each as defined in Formula 5 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 12} , and when n is an integer of 1 to 4, R ₁₂ 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, a heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ 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 to form a condensed ring,
Alkyl group of the R _12, 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 according to claim 1, wherein _{at least one of R 7} , and Ar ₁ to Ar ₅ except for forming a condensation is a substituent represented by the following formula (12).
[Formula 12]

In the above formula (12),
* means a moiety bonded to Formula 1;
L ₂ 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,
R ₁₃ and R ₁₄ are each independently selected from _{the group consisting of a C 1} ~ C ₄₀ alkyl group, a C ₆ ~ C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group or R ₁₃ and R ₁₄ may combine to form a condensed ring;
The _{alkyl group, aryl group, heteroaryl group and arylamine group of R 13} and R ₁₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group having 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 one substituent at least one selected from the group consisting of C ₆ ~ with an aryl silyl group of C ₄₀ of the When substituted or unsubstituted, and the above substituents are plural, they may be the same as or different from each other. The compound according to claim 1, characterized in that the compound is selected from the group consisting of:

The compound according to claim 1, wherein a nitrogen-containing heterocycle is further bonded to the compound.
The compound according to claim 1, wherein at least one substituent selected from the group consisting of an arylamine group, a carbazole group, a terphenyl group, and a triphenylene group is further bonded to the compound.
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 of Formula 1 according to claim 1.
The organic electroluminescent device according to claim 14, wherein the compound represented by Formula 1 is used as a phosphorescent host of the light emitting layer.
The organic electroluminescent device according to claim 14, wherein the compound represented by Formula 1 is used as an electron transport layer.
The organic electroluminescent device according to claim 14, wherein the compound represented by Formula 1 is used as a hole transport layer.