KR102307239B1 - 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 an organic electroluminescent device having characteristics such as high luminous efficiency, low driving voltage, and long lifespan by including the same in one or more organic material layers.

Description

Organic light emitting compound and organic electroluminescent device using 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 organic compound having excellent hole injection and transport ability, electron injection and transport ability, light emitting ability, etc., and the same to one or more organic material layers. By including, it relates to an organic electroluminescent device having improved characteristics such as high luminous efficiency, low driving voltage and lifespan.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') that led to blue electroluminescence using anthracene single crystals in 1965, starting with the observation of organic thin film emission by Bernanose in the 1950s. In 1987, Tang presented an organic EL device with a stacked structure divided into a hole layer and a functional layer of a light emitting layer. 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 EL 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, 4,4-dicarbazolybiphenyl (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, electron 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,

Y ₁ and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , and Y ₉ and Y ₁₀ , Y ₁₀ and Y ₁₁ and Y _{at least one of 11} and Y ₁₂ is condensed with a ring represented by the following formula (2) to form a condensed ring;

[Formula 2]

In Formula 2,

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

In Formulas 1 and 2,

X ₁ and X ₂ are the same as or different from each other, and each independently selected from the group consisting of O, S, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ), and Si(Ar ₄ )(Ar ₅ ) and at least one of _{X 1} and X _{2 is N(Ar 1} );

_{Y 1} to Y ₁₂ not condensed with the ring represented by Formula 2 to form a condensed ring are the same as or different from each other, and are each independently N or C(R ₁ );

When Y ₁₃ to Y ₁₆ are a plurality, they are the same as or different from each other, and Y ₁₃ to Y ₁₆ are each independently N or C(R ₁ );

When R ₁ is a plurality, they are the same or different from each other, and R ₁ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl 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 ₁ ~ 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 It may be selected from the group consisting of an arylamine group, or combine with an adjacent group to form a condensed ring;

When Ar _{1 To} Ar ₅ is a plurality, they are the same or different from each other, and Ar _{1 To} Ar ₅ are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, 3 nuclear atoms. To 40 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 ₁ ~ 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 diaryl phosphinyl group and C ₆ ~ C ₆₀ It may be selected from the group consisting of an arylamine group, or combine with an adjacent group to form a condensed ring;

R ₁ And 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 deuterium, halogen, cyano, a C ₁ ~ C ₄₀ alkyl group, a C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocyclo Alkyl 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 ₁ ~ 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 may be unsubstituted or substituted with one or more substituents selected from the group consisting of a diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, and when substituted with the substituent, the substituent is bonded to an adjacent group to form a condensed ring may be formed, and 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.

According to a preferred embodiment of the present invention, the organic material layer comprising the compound represented by Formula 1 is selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a light emitting auxiliary layer, and a life improvement layer. may be, and preferably, the light emitting layer including the compound represented by Formula 1 may be used as a phosphorescent host.

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 60 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 60 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 an aryl having 6 to 60 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 60 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 novel organic compounds according to the present invention are dibenzoazepine (5H-dibenzo[b,f]azepine), dibenzo[b,f]oxepine, dibenzothiepin (dibenzo[b,f] thiepine), dibenzosilepine (5H-dibenzo[b,f]silepine), or dibenzocycloheptene (5H-dibenzo[a,d]cycloheptene) to form a 5-membered heteroaromatic ring moiety Or, an indene moiety, or an indole moiety is condensed to form a basic skeleton, or benzonaphthoazepine (7H-benzo[b]naphtho[1,2-f]azepine), Benzonaphthooxepin (benzo[b]naphtho[1,2-f]oxepine), benzonaphthothiepin (benzo[b]naphtho[1,2-f]thiepine), benzonaphthocylepine (7H-benzo [b]naphtho[1,2-f]silepine), or benzonaphthocycloheptene (7H-benzo[b]naphtho[1,2-f]cycloheptene) a 5-membered heteroaromatic ring moiety condensed with benzene Alternatively, an indene moiety or an indole moiety may be condensed to form a basic skeleton.

More specifically, the novel organic compound according to the present invention is characterized in that it is represented by the following formula (1).

[Formula 1]

In Formula 1,

Y ₁ and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , and Y ₉ and Y ₁₀ , Y ₁₀ and Y ₁₁ and Y at least one of ₁₁ and Y _{12 , preferably Y 1} and Y ₂ , Y ₇ and Y ₈ and at least one of Y ₁₁ and Y ₁₂ is condensed with a ring represented by the following formula (2) to form a condensed ring;

[Formula 2]

In Formula 2,

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

In Formulas 1 and 2,

X ₁ and X ₂ are the same as or different from each other, and each independently selected from the group consisting of O, S, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ), and Si(Ar ₄ )(Ar ₅ ) and at least one of _{X 1} and X _{2 is N(Ar 1} ), preferably X ₁ is selected from the group consisting of O, S and N(Ar _{1 ), and X 2} is N(Ar ₁ ), and ;

_{Y 1} to Y ₁₂ not condensed with the ring represented by Formula 2 to form a condensed ring are the same as or different from each other, and are each independently N or C(R ₁ );

When Y ₁₃ to Y ₁₆ are a plurality, they are the same as or different from each other, and Y ₁₃ to Y ₁₆ are each independently N or C(R ₁ );

When R ₁ is a plurality, they are the same or different from each other, and R ₁ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl 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 ₁ ~ 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 It may be selected from the group consisting of an arylamine group, or combine with an adjacent group to form a condensed ring;

When Ar _{1 To} Ar ₅ is a plurality, they are the same or different from each other, and Ar _{1 To} Ar ₅ are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, 3 nuclear atoms. To 40 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 ₁ ~ 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 A mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ It may be selected from the group consisting of an arylamine group, or combine with an adjacent group to form a condensed ring;

R ₁ And 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 deuterium, halogen, cyano, a C ₁ ~ C ₄₀ alkyl group, a C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocyclo Alkyl 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 ₁ ~ 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 may be unsubstituted or substituted with one or more substituents selected from the group consisting of a diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, and when substituted with the substituent, the substituent is bonded to an adjacent group to form a condensed ring may be formed, and 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 a conventional material for an organic EL device (eg, 4,4-dicarbazolybiphenyl, hereinafter referred to as 'CBP'), the glass transition It has excellent thermal stability due to high temperature, and excellent carrier transport ability and light emitting ability. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage of the device may be lowered, and efficiency and lifespan may be improved.

In general, in a 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. The compound of Formula 1 has a triplet energy as high as 2.3 eV or more. In addition, in the compound represented by Formula 1, a specific substituent is introduced into the basic skeleton in which an indole derivative having a broad 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. 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 blocking 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, and thus the conventional light emission 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.

The compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas M-1 to M-12.

In Formulas M-1 to M-12, X ₁ , X _{2 ,} and Y ₁ to Y ₁₆ are as defined in Formula 1 above.

However, preferably, the X ₁ is selected from the group consisting of O, S and N(Ar _{1 ), and X 2} may be N(Ar ₁ ).

In addition, preferably, the Y ₁ to Y ₁₆ are the same as or different from each other, and all of them are C(R ₁ ) or may include 1 to 3 N, wherein a plurality of R ₁ are the same or different.

The compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas N-1 to N-12.

In Formulas N-1 to N-12, X ₁ , Ar ₁ and R ₁ are as defined in Formula 1 above.

However, preferably, the X ₁ may be selected from the group consisting of O, S, and N(Ar _{1 ).}

In addition, according to a preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by any one of Formulas 3 to 7 below.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 3 to 7,

When Ar ₁ is plural, they are the same or different from each other, and Ar ₁ are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, or 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 ₁ ~ 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 dia It may be selected from the group consisting of a rilphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring;

Y ₁ to Y ₁₂ are the same as or different from each other, and each independently N or C(R ₁ );

When Y ₁₃ to Y ₁₆ are a plurality, they are the same as or different from each other, and Y ₁₃ to Y ₁₆ are each independently N or C(R ₁ );

When R ₁ is a plurality, they are the same or different from each other, and R ₁ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl 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 ₁ ~ 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 It may be selected from the group consisting of an arylamine group, or combine with an adjacent group to form a condensed ring;

Ar ₁ and R ₁ of 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, an arylphosphine group, The mono or diarylphosphinyl group and the arylamine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl 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 ₁ ~ 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 may be unsubstituted or substituted with one or more substituents selected from the group consisting of a pinyl group and a C ₆ ~ C ₆₀ arylamine group, and when substituted with the substituent, the substituent may combine with an adjacent group to form a condensed ring And, when substituted with a plurality of substituents, they may be the same or different from each other.

However, preferably, in Formulas 3 to 7, Ar ₁ may be a C ₆ ~ C ₆₀ aryl group, and in particular, when Ar ₁ is plural, at least one may be a C ₆ ~ C ₆₀ aryl group. The aryl group may be unsubstituted or substituted with one or more C ₆ ~ C ₆₀ aryl groups, and when substituted with a plurality of substituents, they may be the same or different from each other.

In addition, preferably, in Formula 4, Y ₈ may be C(R ₁ ), and R ₁ may be a C ₆ ~ C ₆₀ aryl group, more preferably a phenyl group.

According to a preferred embodiment of the present invention, when at least one of _{Y 1} to Y ₁₂ that does not form a condensed ring with the ring represented by Formula 2 _{is C(R 1} ), at least one of _{R 1 is a phenyl group} can

According to a preferred embodiment of the present invention _{, at least one of R 1} and Ar ₁ to Ar ₅ may be a phenyl group or a substituent represented by Formula 8 below.

[Formula 8]

In the formula (8),

* means a moiety bonded to Formula 1;

L ₁ is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, preferably a single bond, a phenylene group, a biphenylene group or a carbazolyl group;

Z _{1 To} Z _{5 Are} the same as or different from each other, and each independently represents N or C(R ₁₁ ), wherein at least one of _{Z 1 To} Z _{5 is N;}

When a _{plurality of R 11} is the same or different from each other, R ₁₁ is 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 ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ 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 ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or a neighboring tile that may combine 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, the _{arylene group and heteroarylene group of L 1} are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C group of _40-alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl Phosphinicosuccinic consisting group and a C ₆ ~ C ₆₀ aryl silyl group of the When substituted with one or more substituents selected from the group or unsubstituted, and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by Formula 8 may be a substituent represented by any one of the following O-1 to O-15.

In the above formulas O-1 to O-15,

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 each independently deuterium, halogen, cya. No 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, a heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Arylamine group , C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ Mono or dia A rilphosphinyl group and a C ₆ ~ C ₆₀ 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 _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 ₆₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₆₀ unsubstituted and, when substituted with a plurality of substituents, they may be the same or different from each other;

L ₁ and R ₁₁ are each as defined in Formula 8 above.

According to a preferred embodiment of the present invention, Ar ₁ to Ar ₅ are the same as or different from each other, and may each independently be selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline,

Wherein Ar _{1 To} Ar ₅ Phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline is at least one selected from the group consisting of cyano, phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline. It is substituted or unsubstituted, and when substituted with a plurality of substituents, they may be the same as or different from each other.

The compound represented by Formula 1 of the present invention may be more specifically represented by the following structure as the following compound, but is not limited thereto.

The compound of Formula 1 of the present invention can be synthesized according to a general synthesis method. The detailed synthesis process for the compound of the present invention will be described in detail in the following Synthesis Examples.

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 (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 includes a compound represented by Formula 1 above. In this case, the compound may be used alone or in combination of two or more.

According to an example of the present invention, the at least one organic material layer 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 is represented by Formula 1 above. It may include the indicated compound. Specifically, the organic layer including the compound of Formula 1 is preferably selected from the group consisting of a light emitting layer, an electron transport layer and a hole transport layer, and more preferably a light emitting 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, an electron injection layer may be further laminated on the electron transport layer, and as described above, at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer is represented by Formula 1 compounds may be included.

In addition, the organic electroluminescent device may include a life improvement layer or an electron transport auxiliary layer between the light emitting layer and the electron transport layer. In this case, the compound represented by Formula 1 may be used as a life improvement layer or an electron transport auxiliary 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 SnO _{2 :Sb;} conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.

In addition, 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 multi-layered material such as LiF/Al or LiO ₂ /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 BIAz-1

<Step 1> Synthesis of 1-(5H-dibenzo[b,f]azepin-5-yl)ethanone

5H-dibenzo[b,f]azepine (100.0 g, 517.5 mmol), acetyl chloride (44.3 ml, 621.0 mmol) and toluene (1000 ml) were mixed under a nitrogen stream and stirred at 80° C. for 2 hours.

After completion of the reaction, extraction was performed with ethyl acetate, concentrated, and recrystallized from ethanol to obtain 1-(5H-dibenzo[b,f]azepin-5-yl)ethanone (113.2 g, yield 93%).

¹ H-NMR: δ 1.86 (s, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.26-7.45 (m, 8H)

<Step 2> Synthesis of 1-(1aH-dibenzo[b,f]oxireno[2,3-d]azepin-6(10bH)-yl)ethanone

1- (5H-dibenzo [b,f] azepin-5-yl) ethanone (113.2 g, 481.3 mmol), meta -chloroperoxybenzoic acid (99.7 g, 577.5 mmol), silica (226.5 g) under a nitrogen stream ), NaOCl (226.5 g) and acetonitrile (1100 ml) were mixed and stirred at 80° C. for 2 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, recrystallization with ethanol was carried out to 1-(1aH-dibenzo[b,f]oxyleno[2,3-d]azepin-6(10bH)-yl)ethanone (87.1 g, yield 72) %) was obtained.

¹ H-NMR: δ 1.95 (s, 3H), 4.28 (s, 2H), 7.26-7.53 (m, 8H)

<Step 3> Synthesis of 5-acetyl-5H-dibenzo[b,f]azepin-10(11H)-one

1-(1aH-dibenzo[b,f]oxireno[2,3-d]azepin-6(10bH)-yl)ethanone (87.1 g, 346.5 mmol), lithium iodine (55.7 g, 415.8 mmol) and chloroform (870 ml) were mixed and stirred at 60° C. for 1 hour.

After completion of the reaction, extraction was performed with ethyl acetate, _{water was removed with MgSO 4} , and recrystallized from ethanol to 5-acetyl-5H-dibenzo[b,f]azepin-10(11H)-one (70.5 g, yield 81) %) was obtained.

¹ H-NMR: δ 2.10 (s, 3H), 3.85 (d, 1H), 4.33 (d, 1H), 7.30-7.40 (m, 5H), 7.51-7.59 (m, 2H), 8.10 (d, 1H) )

<Step 4> Synthesis of 5-acetyl-10,11-(1H-benzo[g]indolo)-5H-dibenzo[b,f]azepine

5-acetyl-5H-dibenzo[b,f]azepin-10(11H)-one (70.5 g, 280.7 mmol) and naphthalen-1-ylhydrazine hydrochloride (60.1 g, 308.7 mmol), acetic acid under a nitrogen stream (705 ml) was added and stirred at 120° C. for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:MC = 4:1 (v/v)) to 5-acetyl-10,11-(1H-benzo[g]indolo)-5H-dibenzo [b,f]azepine (68.3 g, yield 65%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 7.25-7.39 (m, 4H), 7.56-7.87 (m, 7H), 8.16 (d, 1H), 8.51 (d, 1H), 9.06 (d, 1H) ), 11.36 (b, 1H)

<Step 5> Synthesis of 5-acetyl-10,11-[1-phenyl benzo[g]indolo]-dibenzo[b,f]azepine

5-acetyl-10,11-(1H-benzo[g]indolo)-5H-dibenzo[b,f]azepine (68.3 g, 350.9 mmol), bromobenzene (66.1 g, 421.1 mmol) under a nitrogen stream ), Cu (11.1 g, 175.5 mmol), K ₂ CO ₃ (97.0 g, 701.8 mmol) and nitrobenzene (683 ml) were mixed and stirred at 210° C. for 12 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated and recrystallized from ethanol to 5-acetyl-10,11-[1-phenylbenzo[g]indolo]-dibenzo[b,f]azepine (123.3 g, yield) 78%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 7.25-7.26 (m, 2H), 7.39-7.58 (m, 9H), 7.77 (d, 1H), 7.87-7.88 (m, 2H), 8.05-8.06 (m, 2H), 8.16 (d, 1H), 8.51 (d, 1H), 9.06 (d, 1H)

<Step 6> Synthesis of BIAz-1

5-acetyl-10,11-[1-phenyl benzo[g]indolo]-dibenzo[b,f]azepine (123.3 g, 273.7 mmol), potassium hydroxide (16.9 g, 301.0 mmol) and Ethylene glycol (1233 ml) was mixed and stirred at 200° C. for 6 hours.

After completion of the reaction, extraction was performed with ethyl acetate, _{water was removed with MgSO 4} , and purified by column chromatography (hexane:EA = 6:1 (v/v)) to obtain BIAz-1 (102.9 g, yield 92%). got it

¹ H-NMR: δ 6.69-6.87 (m, 4H), 7.16-7.17 (m, 2H), 7.45-7.67 (m, 9H), 8.05-8.06 (m, 2H), 8.16 (d, 1H), 8.51 (d, 1H), 8.83 (d, 1H)

[Preparation Example 2] Synthesis of BIAz-2

<Step 1> Synthesis of 5-phenyl-5H-dibenzo[b,f]azepine

5H-dibenzo[b,f]azepine (100 g, 517.5 mmol), iodobenzene (126.7 g, 621.0 mmol), Cu (16.4 g, 258.7 mmol), K ₂ CO ₃ (143.0 g, 1,035.0) under a nitrogen stream mmol) and nitrobenzene (1000 ml) were mixed and stirred at 210° C. for 12 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated, and recrystallized from ethanol to obtain 5-phenyl-5H-dibenzo[b,f]azepine (100.4 g, yield 72%).

¹ H-NMR: δ 6.63-6.81 (m, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.20 (d, 2H), 7.26-7.45 (m, 8H)

<Step 2> Synthesis of 6-phenyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]azepine

5-phenyl-5H-dibenzo[b,f]azepine (100.4 g, 372.6 mmol), meta -chloroperoxybenzoic acid (77.2 g, 447.1 mmol), silica (200.7 g), NaOCl under a nitrogen stream (200.7 g) and acetonitrile (1000 ml) were mixed and stirred at 80° C. for 2 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, recrystallization with ethanol 6-phenyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]azepine (84.0 g, yield 79%) got

¹ H-NMR: δ 4.31 (s, 2H), 6.63-6.81 (m, 3H), 7.24-753 (m, 10H)

<Step 3> Synthesis of 5-phenyl-5H-dibenzo[b,f]azepin-10(11H)-one

6-phenyl-6,10b-dihydro-1aH-dibenzo[b,f]oxireno[2,3-d]azepine (84.0 g, 294.3 mmol), lithium iodine (47.3 g, 353.2 mmol) under a nitrogen stream ) and chloroform (840 ml) were mixed and stirred at 60° C. for 1 hour.

After completion of the reaction, extraction was performed with ethyl acetate, _{water was removed with MgSO 4} , and recrystallized from ethanol to 5-phenyl-5H-dibenzo[b,f]azepin-10(11H)-one (68.0 g, yield 81) %) was obtained.

¹ H-NMR: δ 3.42 (d, 1H), 4.21 (d, 1H), 6.62-6.74 (m, 3H), 7.25-7.40 (m, 7H), 7.51-7.59 (m, 2H), 8.10 (d , 1H)

<Step 4> Synthesis of BIAz-2

5-phenyl-5H-dibenzo[b,f]azepin-10(11H)-one (68.0 g, 238.4 mmol) and naphthalen-1-ylhydrazine hydrochloride under a nitrogen stream (51.1 g, 262.3 mmol) and acetic acid (700 ml) were added, followed by stirring at 120° C. for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:MC = 3:1 (v/v)) to obtain BIAz-2 (59.4 g, yield 61%).

¹ H-NMR: δ 6.63-6.69 (m, 4H), 6.81-6.87 (m, 3H), 7.16-7.20 (m, 4H), 7.54-7.56 (m, 3H), 7.65-7.67 (m, 2H) , 8.16 (d, 1H), 8.51 (d, 1H), 8.83 (d, 1H), 11.36 (b, 1H)

[Preparation Example 3] Synthesis of 13BAz

<Step 1> 1-(naphthalen-1-yl)-1H-indole

1H-indole (100 g, 854.0 mmol), 1-bromonaphthalene (212.1 g, 1024.8 mmol), Cu (27.2 g, 427.0 mmol), K ₂ CO ₃ (236.1 g, 1.70 mol) and nitrobenzene ( 3000 ml) and stirred at 210° C. for 12 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, _{water was removed with MgSO 4} , and purified by column chromatography (hexane:EA = 8:1 (v/v)) to 1-(naphthalen-1-yl)-1H- Indole (182.8 g, yield 88%) was obtained.

¹ H-NMR: δ 6.52 (d, 1H), 6.87 (dd, 1H), 7.33 (dd, 1H), 7.55-7.60 (m, 5H), 7.93-7.94 (m, 2H), 8.06-8.07 (m , 3H)

<Step 2> Synthesis of 13BAz

1-(naphthalen-1-yl)-1H-indole (182.8 g, 751.2 mmol) and polyphosphoric acid (914 g) were mixed under a nitrogen stream and stirred at 100° C. for 12 hours.

After completion of the reaction, the mixture was extracted from water and filtered to obtain 13BAz (58.5 g, yield 32%).

¹ H-NMR: δ 6.81 (dd, 1H), 6.99-7.05 (m, 3H), 7.25-7.29 (m, 2H), 7.53-7.54 (m, 2H), 7.73 (d, 1H), 8.02-8.07 (m, 2H), 8.21 (d, 1H), 8.42 (b, 1H)

[Preparation Example 4] Synthesis of BIAz-3

<Step 1> Synthesis of 1-(13H-benzo [f] naphtho [1,2-b] azepin-13-yl) ethanone

13BAz (100.0 g, 411.0 mmol), acetyl chloride (35.2 ml, 493.2 mmol) and toluene (1000 ml) were mixed under a nitrogen stream and stirred at 80° C. for 2 hours.

After completion of the reaction, extraction with ethyl acetate was performed, concentrated, and recrystallized from ethanol to 1-(13H-benzo[f]naphtho[1,2-b]azepin-13-yl)ethanone (102.0 g, yield 87%) ) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 6.99-7.00 (m, 2H), 7.19-7.28 (m, 3H), 7.48-7.54 (m, 3H), 7.73 (d, 1H), 7.81 (d , 1H), 8.02-8.07 (m, 2H)

<Step 2> Synthesis of 1- (1aH-benzo [f] naphtho [1,2-b] oxireno [2,3-d] azepin-6 (12bH) -yl) ethanone

1- (13H-benzo [f] naphtho [1,2-b] azepin-13-yl) ethanone (102.0 g, 357.6 mmol), meta -chloroperoxybenzoic acid (74.0 g, 429.1 mmol) under a nitrogen stream ), silica (204.1 g), NaOCl (204.1 g) and acetonitrile (1000 ml) were mixed and stirred at 80° C. for 2 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, recrystallization with ethanol was carried out to 1-(1aH-benzo[f]naphtho[1,2-b]oxyleno[2,3-d]azepin-6(12bH)-yl)ethanone (76.5 g, yield 71%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 4.19-4.20 (m, 2H), 6.91 (d, 1H), 7.12 (dd, 1H), 7.34-7.36 (m, 2H), 7.49-7.53 (m) , 3H), 7.74 (d, 1H), 8.03-8.04 (m, 2H)

<Step 3> Synthesis of 13-acetyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azepin-7-one

1- (1aH-benzo [f] naphtho [1,2-b] oxireno [2,3-d] azepin-6 (12bH) -yl) ethanone (76.5 g, 253.9 mmol) under a nitrogen stream, Lithium iodine (40.8 g, 304.7 mmol) and chloroform (750 ml) were mixed and stirred at 60° C. for 1 hour.

After completion of the reaction, extraction was performed with ethyl acetate, _{water was removed with MgSO 4} , and recrystallized from ethanol 13-acetyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azepine -7-one (57.4 g, yield 75%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 3.81 (s, 2H), 7.07 (dd, 1H), 7.21-7.24 (m, 2H), 7.37 (d, 1H), 7.65-7.69 (m, 3H) ), 8.10-8.23 (m, 3H)

<Step 4> Synthesis of 13-acetyl-7,8-(7-phenyl-1H-indolo)-benzo[f]naphtho[1,2-b]azepine

13-acetyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azepin-7-one (57.4 g, 190.4 mmol) and biphenyl-2-ylhydrazine under a nitrogen stream After adding hydrochloride (46.2 g, 209.5 mmol) and acetic acid (600 ml), the mixture was stirred at 120° C. for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:MC = 4:1 (v/v)) to 13-acetyl-7,8-(7-phenyl-1H-indolo)-benzo[f] Naphtho[1,2-b]azepine (52.3 g, yield 61%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 7.14-7.25 (m, 4H), 7.39-7.54 (m, 8H), 7.77-7.87 (m, 4H), 8.02-8.07 (m, 2H), 11.36 (b, 1H)

<Step 5> Synthesis of 13-acetyl-7,8-(7-phenyl-1-(3,5-diphenylbenzene)-indolo)-benzo[f]naphtho[1,2-b]azepine

13-acetyl-7,8- (7-phenyl-1H-indolo)-benzo [f] naphtho [1,2-b] azepine (52.3 g, 237.1 mmol), 1-bromo- under a nitrogen stream Mix 3,5-diphenylbenzene (88.0 g, 284.5 mmol), Cu (7.5 g, 118.6 mmol), K ₂ CO ₃ (65.5 g, 474.2 mmol) and nitrobenzene (500 ml) at 210° C. for 12 hours stirred for a while.

After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated and recrystallized from ethanol to 13-acetyl-7,8-(7-phenyl-1-(3,5-diphenylbenzene)-indolo)-benzo[f]naph To [1,2-b] azepine (112.7 g, yield 70%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 7.19-7.25 (m, 3H), 7.39-7.54 (m, 17H), 7.63 (d, 1H), 7.77-7.78 (m, 2H), 7.87-7.88 (m, 2H), 8.02-8.13 (m, 5H), 8.39 (d, 1H)

<Step 6> Synthesis of BIAz-3

13-acetyl-7,8-(7-phenyl-1-(3,5-diphenylbenzene)-indolo)-benzo[f]naphtho[1,2-b]azepine under a nitrogen stream (112.7 g , 166.0 mmol), potassium hydroxide (10.2 g, 182.6 mmol) and ethylene glycol (1100 ml) were mixed and stirred at 200° C. for 6 hours.

After completion of the reaction, extraction was performed with ethyl acetate, _{water was removed with MgSO 4} , and purified by column chromatography (hexane:EA = 6:1 (v/v)) to obtain BIAz-3 (93.0 g, yield 88%). got it

¹ H-NMR: δ 6.69 (d, 1H), 6.87 (dd, 1H), 7.16-7.19 (m, 3H), 7.41-7.54 (m, 18H), 7.63 (d, 1H), 7.78 (d, 1H) ), 7.88 (s, 1H), 8.02-8.13 (m, 5H), 8.39 (d, 1H)

[Preparation Example 5] Synthesis of BIAz-4

<Step 1> Synthesis of 13-phenyl-13H-benzo [f] naphtho [1,2-b] azepine

13BAz (100 g, 411.0 mmol), iodobenzene (100.6 g, 493.2 mmol), Cu (13.1 g, 205.5 mmol), K ₂ CO ₃ (113.6 g, 822.0 mmol) and nitrobenzene (1000 ml) under a nitrogen stream Mixed and stirred at 210° C. for 12 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated, and recrystallized from ethanol to obtain 13-phenyl-13H-benzo [f] naphtho [1,2-b] azepine (85.3 g, yield 68%).

¹ H-NMR: δ 6.63-6.65 (m, 3H), 6.80-6.81 (m, 2H), 6.99-7.05 (m, 3H), 7.20-7.29 (m, 4H), 7.53-7.54 (m, 2H) , 7.73 (d, 1H), 8.02-8.07 (m, 2H)

<Step 2> Synthesis of 6-phenyl-6,12b-dihydro-1aH-benzo [f] naphtho [1,2-b] oxireno [2,3-d] azepine

13-phenyl-13H-benzo [f] naphtho [1,2-b] azepine (85.3 g, 267.2 mmol), meta -chloroperoxybenzoic acid (55.3 g, 320.6 mmol), silica (170.7 g) under a nitrogen stream ), NaOCl (170.7 g) and acetonitrile (850 ml) were mixed and stirred at 80° C. for 2 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, recrystallization with ethanol was performed to 6-phenyl-6,12b-dihydro-1aH-benzo[f]naphtho[1,2-b]oxyleno[2,3-d]azepine (60.9 g, yield 68%) was obtained.

¹ H-NMR: δ 4.20 (s, 2H), 6.56-6.63 (m, 3H), 6.74-6.81 (m, 2H), 6.91 (d, 1H), 7.11-7.20 (m, 4H), 7.49-7.53 (m, 3H), 8.03-8.04 (m, 2H)

<Step 3> Synthesis of 13-phenyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azepin-7-one

6-phenyl-6,12b-dihydro-1aH-benzo [f] naphtho [1,2-b] oxyleno [2,3-d] azepine (60.9 g, 181.7 mmol), lithium iodine under a nitrogen stream (29.2 g, 218.0 mmol) and chloroform (600 ml) were mixed and stirred at 60° C. for 1 hour.

After completion of the reaction, extraction was performed with ethyl acetate, _{water was removed with MgSO 4} , and recrystallized from ethanol, 13-phenyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azepine -7-one (45.7 g, yield 75%) was obtained.

¹ H-NMR: δ 3.81 (s, 2H), 6.51 (d, 1H), 6.63-6.69 (m, 3H), 6.81 (dd, 1H), 6.98-7.01 (m, 2H), 7.20-7.21 (m) , 2H), 7.37 (d, 1H), 7.65-7.69 (m, 2H), 8.10-8.23 (m, 3H)

<Step 4> Synthesis of BIAz-4

13-phenyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azepin-7-one (45.7 g, 136.3 mmol) and naphthalen-1-ylhydrazine hydro chloride (29.2 g, 149.9 mmol) and acetic acid (450 ml) were added, followed by stirring at 120° C. for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:MC = 3:1 (v/v)) to obtain BIAz-4 (42.5 g, yield 68%).

¹ H-NMR: δ 6.63-6.69 (m, 3H), 6.81-6.87 (m, 2H), 7.16-7.20 (m, 3H), 7.53-7.67 (m, 8H), 7.78 (d, 1H), 8.02 -8.16 (m, 3H), 8.51 (d, 1H), 11.36 (b, 1H)

[Preparation Example 6] Synthesis of BIAz-5

<Step 1> Synthesis of 1a,10b-dihydrodibenzo[b,f]oxireno[2,3-d]oxepin

Dibenzo[b,f]oxepin (100.0 g, 514.9 mmol), meta -chloroperoxybenzoic acid (106.6 g, 617.8 mmol), silica (200.0 g), NaOCl under a nitrogen stream (200.0 g) and acetonitrile (1000 ml) were mixed and stirred at 80° C. for 2 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 recrystallized with ethanol to obtain 1a,10b-dihydrodibenzo[b,f]oxyreno[2,3-d]oxepin (87.7 g, yield 81%).

¹ H-NMR: δ 4.30 (s, 2H), 7.10 (d, 2H), 7.26-7.34 (m, 6H)

<Step 2> Synthesis of dibenzo [b, f] oxepin-10 (11H) -one

1a,10b-dihydrodibenzo[b,f]oxireno[2,3-d]oxepin (87.7 g, 417.0 mmol), lithium iodine (67.0 g, 500.4 mmol) and chloroform (900 ml) under a nitrogen stream ) and stirred at 60° C. for 1 hour.

After completion of the reaction, extraction was performed with ethyl acetate, _{water was removed with MgSO 4} , and recrystallized from ethanol to obtain dibenzo[b,f]oxepin-10(11H)-one (69.3 g, yield 79%).

¹ H-NMR: δ 3.51 (d, 1H), 4.42 (d, 1H), 7.05 (t, 1H), 7.19-7.28 (m, 4H), 7.43-7.44 (m, 2H), 7.60 (t, 1H) )

<Step 3> Synthesis of BIAz-5

Dibenzo[b,f]oxepin-10(11H)-one (69.3 g, 329.5 mmol) and naphthalen-1-ylhydrazine hydrochloride under a nitrogen stream (70.5 g, 362.4 mmol) and acetic acid (700 ml) were added, followed by stirring at 120° C. for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:MC = 3:1 (v/v)) to obtain BIAz-5 (56.0 g, yield 51%).

¹ H-NMR: δ 7.20-7.23 (m, 4H), 7.36-7.37 (m, 2H), 7.55-7.56 (m, 2H), 7.67-7.75 (m, 3H), 8.16 (d, 1H), 8.39 (d, 1H), 8.51 (d, 1H), 11.36 (b, 1H)

[Preparation Example 7] Synthesis of BAz-6

<Step 1> Synthesis of 1a,10b-dihydrodibenzo[b,f]oxireno[2,3-d]thiepin

Dibenzo[b,f]thiepin (100.0 g, 475.5 mmol), meta -chloroperoxybenzoic acid (98.5 g, 570.6 mmol), silica (200.0 g), NaOCl under a nitrogen stream (200.0 g) and acetonitrile (1000 ml) were mixed and stirred at 80° C. for 2 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 recrystallized with ethanol to obtain 1a,10b-dihydrodibenzo[b,f]oxyreno[2,3-d]thiepin (80.7 g, yield 75%).

¹ H-NMR: δ 4.40 (s, 2H), 7.12-7.16 (m, 4H), 7.45 (t, 2H), 7.70 (d, 2H)

<Step 2> Synthesis of dibenzo[b,f]thiepin-10(11H)-one

1a,10b-dihydrodibenzo[b,f]oxireno[2,3-d]thiepin (80.7 g, 356.7 mmol), lithium iodine (57.3.0 g, 428.0 mmol) and chloroform ( 800 ml) and stirred at 60° C. for 1 hour.

After completion of the reaction, extraction was performed with ethyl acetate, _{water was removed with MgSO 4} , and recrystallized from ethanol to obtain dibenzo[b,f]thiepin-10(11H)-one (59.7 g, yield 74%).

¹ H-NMR: δ 3.61 (d, 1H), 4.47 (d, 1H), 7.03-7.07 (m, 2H), 7.30-7.33 (m, 2H), 7.44-7.52 (m, 2H), 7.65 (d , 1H), 7.74 (d, 1H)

<Step 3> Synthesis of BIAz-6

Dibenzo[b,f]thiepin-10(11H)-one (59.7 g, 263.9 mmol) and naphthalen-1-ylhydrazine hydrochloride under a nitrogen stream (56.5 g, 290.3 mmol) and acetic acid (600 ml) were added, followed by stirring at 120° C. for 12 hours.

After completion of the reaction, extraction was performed with dichloromethane, MgSO ₄ was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:MC = 3:1 (v/v)) to obtain BIAz-6 (50.7 g, yield 55%).

¹ H-NMR: δ 7.21-7.25 (m, 4H), 7.47-7.67 (m, 8H), 8.16 (d, 1H), 8.51 (d, 1H), 11.36 (b, 1H)

[Synthesis Example 1] Synthesis of A-1

BIAz-1 (2.7 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol), P( t) under a nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound A-1 (2.7 g, yield 64%).

Mass (theoretical: 637.58, measured: 637 g/mol)

[Synthesis Example 2] Synthesis of A-2

The same procedure as in Synthesis Example 1 was followed except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound A-2 (2.9 g, yield 68%) was obtained.

Mass (theoretical: 638.57, measured: 638 g/mol)

[Synthesis Example 3] Synthesis of A-3

Synthesis Example 1, except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine The same procedure was performed to obtain the target compound, A-3 (2.8 g, yield 65%).

Mass (theoretical: 638.57, measured: 638 g/mol)

[Synthesis Example 4] Synthesis of A-4

The same as in Synthesis Example 1 except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine The process was carried out to obtain the target compound, A-4 (3.0 g, yield 63%).

Mass (theoretical: 714.6, measured: 714 g/mol)

[Synthesis Example 5] Synthesis of A-5

Except for using 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-5 (3.2 g, yield 67%).

Mass (theoretical value: 715.6, measured value: 715 g/mol)

[Synthesis Example 6] Synthesis of A-6

2-(3-bromophenyl-3-yl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) was replaced with 2-bromo-4,6-diphenylpyridine Except for using, the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-6 (2.9 g, yield 61%).

Mass (theoretical value: 715.6, measured value: 715 g/mol)

[Synthesis Example 7] Synthesis of A-7

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-bromo-4,6-diphenylpyridine (3.7 g, 8.0 mmol) A target compound A-7 (3.5 g, yield 66%) was obtained in the same manner as in Synthesis Example 1 except for using .

Mass (theoretical: 792.64, measured: 792 g/mol)

[Synthesis Example 8] Synthesis of A-8

Synthesis Example 1 except for using 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine The same procedure was performed to obtain the target compound, A-8 (3.2 g, yield 64%).

Mass (theoretical: 738.6, measured: 738 g/mol)

[Synthesis Example 9] Synthesis of A-9

The target compound was carried out in the same manner as in Synthesis Example 1, except that 2-(3-bromophenyl)triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Phosphorus A-9 (3.0 g, yield 63%) was obtained.

Mass (theoretical value: 710.60, measured value: 710 g/mol)

[Synthesis Example 10] Synthesis of A-10

The same procedure as in Synthesis Example 1 was performed except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine to obtain the target compound. A-10 (2.7 g, yield 70%) was obtained.

Mass (theoretical: 585.6, measured: 585 g/mol)

[Synthesis Example 11] Synthesis of B-1

BIAz-2 (2.7 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol), P( t) under a nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110° C. for 5 hours. After completion of the reaction, toluene was concentrated, the solid salt was filtered and purified by recrystallization to obtain the target compound B-1 (2.9 g, yield 68%).

Mass (theoretical: 637.58, measured: 637 g/mol)

[Synthesis Example 12] Synthesis of B-2

The same procedure as in Synthesis Example 11 was performed except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound B-2 (3.0 g, yield 71%) was obtained.

Mass (theoretical: 638.57, measured: 638 g/mol)

[Synthesis Example 13] Synthesis of B-3

Except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine, as in Synthesis Example 11 The same procedure was followed to obtain the target compound, B-3 (2.7 g, yield 63%).

Mass (theoretical: 638.57, measured: 638 g/mol)

[Synthesis Example 14] Synthesis of B-4

The same procedure as in Synthesis Example 11, except that 4-(4-bromophenyl)-2,6-dipyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine to obtain the target compound, B-4 (3.2 g, yield 66%).

Mass (theoretical: 714.6, measured: 714 g/mol)

[Synthesis Example 15] Synthesis of B-5

Except for using 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 11 was performed to obtain the target compound, B-5 (3.4 g, yield 70%).

Mass (theoretical value: 715.6, measured value: 715 g/mol)

[Synthesis Example 16] Synthesis of B-6

Except for using 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 11 was performed to obtain the target compound, B-6 (3.1 g, yield 65%).

Mass (theoretical value: 715.6, measured value: 715 g/mol)

[Synthesis Example 17] Synthesis of B-7

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-bromo-4,6-diphenylpyridine (3.7 g, 8.0 mmol) The same procedure as in Synthesis Example 11 was performed except for using the target compound, B-7 (3.3 g, yield 62%).

Mass (theoretical: 792.64, measured: 792 g/mol)

[Synthesis Example 18] Synthesis of B-8

Synthesis Example 11 except that 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (2.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine By performing the same procedure as to obtain the target compound, B-8 (3.4 g, yield 70%).

Mass (theoretical: 738.6, measured: 738 g/mol)

[Synthesis Example 19] Synthesis of B-9

The target compound was carried out in the same manner as in Synthesis Example 11, except that 2-(3-bromophenyl)triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Phosphorus B-9 (3.0 g, yield 64%) was obtained.

Mass (theoretical value: 710.60, measured value: 710 g/mol)

[Synthesis Example 20] Synthesis of B-10

The same procedure as in Synthesis Example 11 was performed except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine to obtain the target compound. B-10 (2.7 g, yield 68%) was obtained.

Mass (theoretical: 585.6, measured: 585 g/mol)

[Synthesis Example 21] Synthesis of C-1

BIAz-3 (2.7 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol), P( t) under a nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound C-1 (3.8 g, yield 66%).

Mass (theoretical: 865.87, measured: 865 g/mol)

[Synthesis Example 22] Synthesis of C-2

The same procedure as in Synthesis Example 21 was performed except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound C-2 (3.5 g, yield 61%) was obtained.

Mass (theoretical: 866.86, measured: 866 g/mol)

[Synthesis Example 23] Synthesis of C-3

Synthesis Example 21, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine The same procedure was followed to obtain the target compound, C-3 (3.8 g, yield 65%).

Mass (theoretical: 866.86, measured: 866 g/mol)

[Synthesis Example 24] Synthesis of C-4

The same as in Synthesis Example 11 except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine The process was carried out to obtain the target compound, C-4 (4.3 g, yield 68%).

Mass (theoretical value: 942.89, measured value: 942 g/mol)

[Synthesis Example 25] Synthesis of C-5

Except for using 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 21 was performed to obtain the target compound, C-5 (3.9 g, yield 61%).

Mass (theoretical value: 943.89, measured value: 943 g/mol)

[Synthesis Example 26] Synthesis of C-6

Except for using 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 21 was performed to obtain the target compound, C-6 (4.5 g, yield 71%).

Mass (theoretical value: 943.89, measured value: 943 g/mol)

[Synthesis Example 27] Synthesis of C-7

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-bromo-4,6-diphenylpyridine (3.7 g, 8.0 mmol) The same procedure as in Synthesis Example 21 was performed except for using the target compound, C-7 (4.9 g, yield 72%).

Mass (theoretical value: 1020.93, measured value: 1020 g/mol)

[Synthesis Example 28] Synthesis of C-8

Synthesis Example 21 except for using 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine By the same procedure as described above, the target compound, C-8 (4.2 g, yield 65%) was obtained.

Mass (theoretical value: 966.89, measured value: 966 g/mol)

[Synthesis Example 29] Synthesis of C-9

The target compound was carried out in the same manner as in Synthesis Example 21, except that 2-(3-bromophenyl)triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Phosphorus C-9 (4.2 g, yield 66%) was obtained.

Mass (theoretical value: 938.89, measured value: 938 g/mol)

[Synthesis Example 30] Synthesis of C-10

The same procedure as in Synthesis Example 21 was followed except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine to obtain the target compound. C-10 (3.3 g, yield 61%) was obtained.

Mass (theoretical: 813.8, measured: 813 g/mol)

[Synthesis Example 31] Synthesis of D-1

BIAz-4 (2.7 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol), P( t) under a nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound D-1 (3.0 g, yield 65%).

Mass (theoretical: 687.64, measured: 687 g/mol)

[Synthesis Example 32] Synthesis of D-2

The same procedure as in Synthesis Example 31 was followed except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound D-2 (3.2 g, yield 69%) was obtained.

Mass (theoretical value: 688.63, measured value: 688 g/mol)

[Synthesis Example 33] Synthesis of D-3

Synthesis Example 31, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine The same procedure was performed to obtain the target compound, D-3 (3.0 g, yield 66%).

Mass (theoretical value: 688.63, measured value: 688 g/mol)

[Synthesis Example 34] Synthesis of D-4

The same as in Synthesis Example 31 except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine The process was carried out to obtain the target compound, D-4 (3.4 g, yield 67%).

Mass (theoretical: 764.66, measured: 764 g/mol)

[Synthesis Example 35] Synthesis of D-5

Except for using 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 31 was performed to obtain the target compound, D-5 (3.1 g, yield 61%).

Mass (theoretical: 765.66, measured: 765 g/mol)

[Synthesis Example 36] Synthesis of D-6

Except for using 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 31 was performed to obtain the target compound, D-6 (3.1 g, yield 61%).

Mass (theoretical: 765.66, measured: 765 g/mol)

[Synthesis Example 37] Synthesis of D-7

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-bromo-4,6-diphenylpyridine (3.7 g, 8.0 mmol) The same procedure as in Synthesis Example 31 was performed except for using the target compound, D-7 (3.6 g, yield 63%).

Mass (theoretical value: 842.7, measured value: 842 g/mol)

[Synthesis Example 38] Synthesis of D-8

Synthesis Example 31 except for using 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine By the same procedure as described above, the target compound, D-8 (3.5 g, yield 66%) was obtained.

Mass (theoretical value: 788.66, measured value: 788 g/mol)

[Synthesis Example 39] Synthesis of D-9

The target compound was carried out in the same manner as in Synthesis Example 31, except that 2-(3-bromophenyl)triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Phosphorus D-9 (3.5 g, yield 69%) was obtained.

Mass (theoretical value: 760.66, measured value: 760 g/mol)

[Synthesis Example 40] Synthesis of D-10

The same procedure as in Synthesis Example 31 was performed except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine to obtain the target compound. D-10 (3.1 g, yield 72%) was obtained.

Mass (theoretical value: 635.6, measured value: 635 g/mol)

[Synthesis Example 41] Synthesis of E-1

BIAz-5 (2.7 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol), P( t) under a nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110° C. for 5 hours. After completion of the reaction, toluene was concentrated, the solid salt was filtered and purified by recrystallization to obtain the target compound E-1 (2.4 g, yield 64%).

Mass (theoretical: 562.47, measured: 562 g/mol)

[Synthesis Example 42] Synthesis of E-2

The same procedure as in Synthesis Example 41 was followed except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound E-2 (2.6 g, yield 69%) was obtained.

Mass (theoretical: 563.46, measured: 563 g/mol)

[Synthesis Example 43] Synthesis of E-3

Synthesis Example 41, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine The same procedure was performed to obtain the target compound, E-3 (2.6 g, yield 70%).

Mass (theoretical: 563.46, measured: 563 g/mol)

[Synthesis Example 44] Synthesis of E-4

The same as in Synthesis Example 41 except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine The process was carried out to obtain the target compound E-4 (3.1 g, yield 73%).

Mass (theoretical: 639.49, measured: 639 g/mol)

[Synthesis Example 45] Synthesis of E-5

Except for using 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 41 was performed to obtain the target compound E-5 (2.8 g, yield 65%).

Mass (theoretical: 640.49, measured: 640 g/mol)

[Synthesis Example 46] Synthesis of E-6

Except for using 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 41 was performed to obtain the target compound E-6 (2.8 g, yield 65%).

Mass (theoretical: 640.49, measured: 640 g/mol)

[Synthesis Example 47] Synthesis of E-7

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-bromo-4,6-diphenylpyridine (3.7 g, 8.0 mmol) The same procedure as in Synthesis Example 41 was performed except for using E-7, which is the target compound (3.5 g, yield 72%).

Mass (theoretical value: 717.53, measured value: 717 g/mol)

[Synthesis Example 48] Synthesis of E-8

Synthesis Example 41 except for using 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine By the same procedure as described above, the target compound E-8 (3.4 g, yield 77%) was obtained.

Mass (theoretical: 663.49, measured: 663 g/mol)

[Synthesis Example 49] Synthesis of E-9

The target compound was carried out in the same manner as in Synthesis Example 41, except that 2-(3-bromophenyl)triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Phosphorus E-9 (3.1 g, yield 73%) was obtained.

Mass (theoretical: 635.49, measured: 635 g/mol)

[Synthesis Example 50] Synthesis of E-10

The same procedure as in Synthesis Example 41 was performed except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine to obtain the target compound. E-10 (2.4 g, yield 73%) was obtained.

Mass (theoretical value: 510.44, measured value: 510 g/mol)

[Synthesis Example 51] Synthesis of F-1

BIAz-6 (2.7 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd(OAc) ₂ (0.08 g, 0.34 mmol), P( t) under a nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound F-1 (2.4 g, yield 63%).

Mass (theoretical: 578.54, measured: 578 g/mol)

[Synthesis Example 52] Synthesis of F-2

The same procedure as in Synthesis Example 51 was followed except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound F-2 (2.7 g, yield 69%) was obtained.

Mass (theoretical: 579.53, measured: 579 g/mol)

[Synthesis Example 53] Synthesis of F-3

Except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine, as in Synthesis Example 51 The same procedure was followed to obtain the target compound, F-3 (2.9 g, yield 74%).

Mass (theoretical: 579.53, measured: 579 g/mol)

[Synthesis Example 54] Synthesis of F-4

The same as in Synthesis Example 51 except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine The process was carried out to obtain the target compound, F-4 (3.3 g, yield 76%).

Mass (theoretical value: 655.56, measured value: 655 g/mol)

[Synthesis Example 55] Synthesis of F-5

Except for using 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 51 was performed to obtain the target compound, F-5 (3.1 g, yield 70%).

Mass (theoretical: 656.56, measured: 656 g/mol)

[Synthesis Example 56] Synthesis of F-6

Except for using 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 51 was performed to obtain the target compound, F-6 (3.1 g, yield 71%).

Mass (theoretical: 656.56, measured: 656 g/mol)

[Synthesis Example 57] Synthesis of F-7

2-(3'-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine e instead of 2-bromo-4,6-diphenylpyridine (3.7 g, 8.0 mmol ) was carried out in the same manner as in Synthesis Example 51, except that the target compound F-7 (3.6 g, yield 73%) was obtained.

Mass (theoretical value: 733.60, measured value: 733 g/mol)

[Synthesis Example 58] Synthesis of F-8

Synthesis Example 51 except for using 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine The same procedure was performed to obtain the target compound, F-8 (3.2 g, yield 70%).

Mass (theoretical: 679.56, measured: 679 g/mol)

[Synthesis Example 59] Synthesis of F-9

In the same manner as in Synthesis Example 51, except for using 2-(3-bromophenyl)triphenylene (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine, the target compound Phosphorus F-9 (3.1 g, yield 72%) was obtained.

Mass (theoretical: 651.56, measured: 651 g/mol)

[Synthesis Example 60] Synthesis of F-10

The same procedure as in Synthesis Example 51 was performed except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine to obtain the target compound. F-10 (2.3 g, yield 65%) was obtained.

Mass (theoretical: 526.51, measured: 526 g/mol)

[Examples 1 to 54] Fabrication of green organic EL device

After high-purity sublimation purification of the compound synthesized in the above synthesis example by a commonly known method, 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, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes and vacuum evaporator The substrate was transferred to

On the thus prepared ITO transparent electrode, m-MTDATA (60 nm)/TCTA (80 nm)/ 90% Host compound of Table 1 below + 10% Ir(ppy) ₃ (300 nm)/BCP (10 nm)/Alq 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-1 as a light emitting host material when the light emitting layer was formed.

[Evaluation Example 1]

For each of the green organic EL devices manufactured in Examples 1 to 54 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 EL peak current efficiency (V) (nm) (cd/A) Example 1 A-1 6.77 517 41.3 Example 2 A-2 6.46 515 41.3 Example 3 A-3 6.81 518 39.7 Example 4 A-4 6.68 518 38.9 Example 5 A-5 6.66 517 41.5 Example 6 A-6 6.48 518 39.2 Example 7 A-7 6.48 517 41.3 Example 8 A-9 6.86 515 39.7 Example 9 A-10 6.48 518 38.9 Example 10 B-1 6.48 518 41.3 Example 11 B-2 6.86 517 41.3 Example 12 B-3 6.77 515 41.3 Example 13 B-4 6.66 518 41.2 Example 14 B-5 6.65 518 38.9 Example 15 B-6 6.65 517 41.3 Example 16 B-7 6.64 515 41.3 Example 17 B-9 6.64 518 41.3 Example 18 B-10 6.64 518 41.2 Example 19 C-1 6.81 517 42.2 Example 20 C-2 6.66 515 42 Example 21 C-3 6.81 518 39.7 Example 22 C-4 6.68 518 38.9 Example 23 C-5 6.66 518 41.3 Example 24 C-6 6.7 517 41.3 Example 25 C-7 6.7 515 43.1 Example 26 C-9 6.51 518 43.5 Example 27 C-10 6.77 518 41.4 Example 28 D-1 6.7 515 43.1 Example 29 D-2 6.51 518 43.5 Example 30 D-3 6.77 518 41.4 Example 31 D-4 6.46 518 42.2 Example 32 D-5 6.81 517 42 Example 33 D-6 6.68 515 41.8 Example 34 D-7 6.66 515 41.3 Example 35 D-9 6.48 518 41.2 Example 36 D-10 6.66 518 41.3 Example 37 E-1 6.86 517 41.2 Example 38 E-2 6.77 515 42 Example 39 E-3 6.66 518 39.7 Example 40 E-4 6.77 518 38.9 Example 41 E-5 6.46 515 41.3 Example 42 E-6 6.81 518 41.3 Example 43 E-7 6.73 518 43.1 Example 44 E-9 6.73 517 43.5 Example 45 E-10 6.73 515 41.4 Example 46 F-1 6.48 515 43.1 Example 47 F-2 6.86 518 43.5 Example 48 F-3 6.73 518 41.4 Example 49 F-4 6.48 517 41.5 Example 50 F-5 6.86 515 39.2 Example 51 F-6 6.77 518 41.3 Example 52 F-7 6.66 517 39.7 Example 53 F-9 6.65 518 38.9 Example 54 F-10 6.65 517 41.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound according to the present invention is used in the light emitting layer of the green organic EL device (Examples 1 to 54), the efficiency and It was confirmed that the driving voltage was excellent.

[Examples 55 to 60] Preparation of red organic EL device

After high-purity sublimation purification of the compound synthesized in the above 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, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes and vacuum evaporator The substrate was transferred to

m-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent electrode + 10% (piq) ₂ Ir (acac) (300 nm) / BCP (10 nm) / Alq of Table 2 below ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate an organic electroluminescent device.

[Comparative Example 2] Preparation of red organic EL device

A red organic electroluminescent device was manufactured in the same manner as in Example 55, except that CBP was used instead of Compound A-8 of Synthesis Example 8 as a light emitting host material when the emission layer was formed.

The structures of m-MTDATA, (piq) ₂ Ir(acac), CBP and BCP used in Examples 55 to 60 and Comparative Example 2 are as follows.

[Evaluation Example 2]

For each organic electroluminescent device manufactured in Examples 55 to 60 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 drive voltage current efficiency (V) (cd/A) Example 55 A-8 4.65 11.8 Example 56 B-8 4.74 11.5 Example 57 C-8 4.87 11.8 Example 58 D-8 4.74 11.5 Example 59 E-8 4.87 11.8 Example 60 F-8 4.56 9.6 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention is used in the light emitting layer of the red organic electroluminescent device (Examples 55 to 60), the efficiency and It was confirmed that the driving voltage was excellent.

[Example 61] Manufacturing 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. Then, the substrate was transferred to a vacuum laminating machine.

On the ITO transparent electrode prepared as above, m-MTDATA (60 nm) / Compound A-9 (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq3 (30) synthesized in Synthesis Example 9 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 62 to 66] Preparation of organic EL devices

Except for using each synthesized compound B-9, C-9, D-9, E-9, F-9 instead of compound A-9 used as a hole transport layer material when forming the hole transport layer in Example 61, An organic EL device was manufactured in the same manner as in Example 61.

[Comparative Example 3] Preparation of organic EL device

An organic EL device was manufactured in the same manner as in Example 61, except that NPB was used as the hole transport layer material instead of Compound A-9 used as the hole transport layer material when the hole transport layer was formed in Example 61. 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 61 to 66 and Comparative Example 3, and the results are shown in Table 3 below.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example 61 A-9 4.4 19.8 Example 62 B-9 4.2 19.2 Example 63 C-9 4.3 18.9 Example 64 D-9 4.4 19.2 Example 65 E-9 4.2 18.9 Example 66 F-9 4.9 20.1 Comparative Example 3 NPB 5.2 18.1

As shown in Table 3, the organic EL devices (organic EL devices prepared in Examples 61 to 66, respectively) using the compounds (A-9 to F-9) 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) exhibited better performance in terms of current efficiency and driving voltage.

[Example 67] Manufacturing of blue organic EL device

After high-purity sublimation purification of Compound A-1 synthesized in Synthesis Example 1 by a commonly known method, a blue organic electroluminescent device was prepared as follows.

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. After cleaning, the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (80 nm)/NPB (15 nm)/AND + 5% DS-405 (30 nm)/Compound A-1 (5 nm)/Alq3 (25 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device.

The structures of NPB, AND and Alq ₃ used at this time are as follows.

[Example 68] to [Example 108] Preparation of blue organic EL device

A blue organic EL device was manufactured in the same manner as in Example 67, except that each compound shown in Table 4 was used instead of Compound A-1 used as a material for the life improvement layer in Example 67.

[Comparative Example 4] Preparation of blue organic EL device

A blue organic electroluminescent device was manufactured in the same manner as in Example 67, except that the life improvement layer was not included, and Alq _{3 , which is an electron transport layer material, was deposited at 30 nm instead of 25 nm.}

[Comparative Example 5] Preparation of blue organic EL device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that BCP was used instead of using Compound A-1 used as a material for the life improvement layer in Example 67.

The structure of the BCP used at this time is as follows.

[Evaluation Example 4]

For the organic electroluminescent devices prepared in Examples 67 to 109 and Comparative Examples 4 and 5, respectively, the driving voltage, current efficiency, emission wavelength and lifetime (T97) at a current density of 10 mA/cm 2 were measured, and the results were It is shown in Table 4 below.

Sample Life improvement layer drive voltage current efficiency EL peak life span (V) (cd/A) (nm) (hr, T ₉₇ ) Example 67 A-1 4.8 5.9 463 41 Example 68 A-2 4.2 5.9 465 42 Example 69 A-3 5.0 6.0 469 43 Example 70 A-4 5.1 6.2 461 45 Example 71 A-5 5.2 6.3 462 48 Example 72 A-6 4.5 6.4 458 38 Example 73 A-7 5.3 6.0 458 37 Example 74 B-1 5.1 6.1 459 32 Example 75 B-2 5.2 6.1 460 39 Example 76 B-3 4.3 5.9 461 43 Example 77 B-4 4.2 5.9 463 45 Example 78 B-5 4.3 6.4 465 48 Example 79 B-6 4.2 6.3 469 38 Example 80 B-7 4.8 6.1 461 37 Example 81 C-1 4.9 6.1 462 32 Example 82 C-2 5.2 5.9 451 45 Example 83 C-3 5.3 5.9 457 48 Example 84 C-4 5.3 6.3 459 38 Example 85 C-5 5.2 5.9 459 37 Example 86 C-6 5.0 6.4 459 32 Example 87 C-7 5.0 6.3 451 39 Example 88 D-1 4.9 6.1 459 43 Example 89 D-2 4.9 6.1 460 45 Example 90 D-3 4.9 5.9 461 44 Example 91 D-4 5.0 5.9 463 40 Example 92 D-5 4.9 6.3 465 42 Example 93 D-6 4.9 5.9 469 40 Example 94 D-7 4.9 6.2 461 40 Example 95 E-1 4.8 6.1 462 41 Example 96 E-2 4.2 6.1 451 44 Example 97 E-3 4.2 6.0 458 38 Example 98 E-4 4.1 5.9 458 40 Example 99 E-5 4.1 5.9 461 33 Example 100 E-6 4.1 6.0 462 32 Example 101 E-7 4.1 6.2 465 38 Example 102 F-1 4.0 6.3 469 40 Example 103 F-2 5.1 6.4 461 42 Example 104 F-3 5.1 6.0 462 40 Example 105 F-4 5.3 6.1 465 40 Example 106 F-5 4.8 6.1 469 41 Example 107 F-6 4.9 6.0 458 39 Example 108 F-7 5.0 6.1 458 42 Comparative Example 4 - 4.7 5.6 458 32 Comparative Example 5 BCP 5.3 5.9 458 28

As can be seen from Table 4, in the case of the blue organic EL devices of Examples 67 to 108 using the compounds A-1 to F-7 as the life improvement layer material, the blue color of Comparative Example 4 not using the life improvement layer Although the driving voltage of the organic EL device is similar or slightly superior to that of the organic EL device, the current efficiency and lifespan are greatly improved.

In addition, the blue organic EL devices of Examples 67 to 108 have excellent driving voltage and current efficiency, as well as superior lifespan, compared to the blue organic EL devices of Comparative Example 5 in which CBP is used as a hole blocking layer material instead of a life improvement layer. improved considerably.

[Example 109] Manufacturing of blue organic EL device

After high-purity sublimation purification of Compound A-5 synthesized in Synthesis Example 5 by a commonly known method, a blue organic electroluminescent device was prepared as follows.

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. After cleaning, the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (80 nm)/NPB (15 nm)/AND + 5% DS-405 (30 nm)/Compound A-5 (30 nm)/LiF (1 nm)/Al ( 200 nm) to prepare an organic electroluminescent device.

[Example 110] to [Example 114] Preparation of blue organic EL device

A blue organic EL device was manufactured in the same manner as in Example 109, except that each compound shown in Table 5 was used instead of Compound A-5 used as an electron transport layer material in Example 109.

[Comparative Example 6] Preparation of blue organic EL device

A blue organic electroluminescent device was manufactured in the same manner as in Example 108, except that it _{does not include a lifespan improvement layer, and deposits Alq 3} , which is an electron transport layer material, at 30 nm instead of 25 nm.

[Evaluation Example 5]

For the organic electroluminescent devices prepared in Examples 109 to 114 and Comparative Example 6, respectively, the driving voltage, current efficiency, emission wavelength and lifetime (T97) at a current density of 10 mA/cm 2 were measured, and the results are shown in the table below 5 is shown.

Sample electron transport layer drive voltage
(V) current efficiency
(cd/A) luminescence peak
(nm) Example 109 A-5 4.5 5.8 463 Example 110 B-5 4.2 6.1 462 Example 111 C-5 4.0 6.3 460 Example 112 D-5 4.2 5.8 462 Example 113 E-5 4.0 6.1 460 Example 114 F-5 4.7 6.0 459 Comparative Example 6 _ 4.7 5.6 458

As shown in Table 5, in the case of the blue organic EL devices of Examples 109 to 114 using the compounds A-5 to F-5 as the electron transport layer material, the blue organic EL device of Comparative Example 6 using _{Alq 3 as the electron transport layer} Compared to that, the driving voltage and current efficiency were further improved.

As such, it was confirmed that, when the compound of Formula 1 according to the present invention was used as a material for a life improvement layer or an electron transport layer, driving voltage and current efficiency were improved, and further, lifespan characteristics could be greatly improved.

Claims (17)

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

In Formula 1,
At least _one of Y 1 and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₇ and Y ₈ , and Y ₉ and Y ₁₀ , Y ₁₀ and Y ₁₁ , Y ₁₁ and Y ₁₂ is represented by the following formula (2) condensed with the indicated ring to form a condensed ring;
[Formula 2]

In Formula 2,
The dotted line is the part where the condensation takes place;
In Formulas 1 and 2,
X ₁ and X ₂ are the same as or different from each other, and each independently selected from the group consisting of O, S, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ), and Si(Ar ₄ )(Ar ₅ ) and at least one of _{X 1} and X _{2 is N(Ar 1} );
_{Y 1} to Y ₁₂ not condensed with the ring represented by Formula 2 to form a condensed ring are the same as or different from each other, and are each independently N or C(R ₁ );
When Y ₁₃ to Y ₁₆ are a plurality, they are the same as or different from each other, and Y ₁₃ to Y ₁₆ are each independently N or C(R ₁ );
When R ₁ is a plurality, they are the same or different from each other, and R ₁ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl 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 ₁ ~ 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} is selected from the group consisting of an arylamine group, or combines with an adjacent group to form a condensed ring;
Ar _{1 To} Ar _{5 Are} the same as or different from each other, and each independently hydrogen, a C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ of an aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and C of ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, or combined with an adjacent group to form a condensed ring;
The Ar _{1 To} Ar ₅ And R ₁ Of 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, The arylphosphine group, the mono or diarylphosphinyl group and the arylamine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms hetero Cycloalkyl group, 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 ₁ ~ C ₄₀ alkyl Silyl 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 a diarylphosphinyl group and a C ₆ ~ C ₆₀ arylamine group substituted or unsubstituted with one or more substituents selected from the group consisting of, and when substituted with the substituent, the substituent may combine with an adjacent group to form a condensed ring. and when substituted with a plurality of substituents, they may be the same as or different from each other.
According to claim 1,
Y ₁ and Y ₂ , Y ₇ and Y ₈ and At least one of Y ₁₁ and Y ₁₂ is condensed with a ring represented by the following formula (2) to form a condensed ring:
[Formula 2]

In Formula 2,
The dotted line and Y ₁₃ to Y ₁₆ are as defined in claim 1.
According to claim 1,
Wherein X ₁ is selected from the group consisting of O, S and N(Ar _{1 ), and X 2} is N(Ar ₁ ) A compound, characterized in that.
According to claim 1,
The compound represented by Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas M-1 to M-3, and Chemical Formulas M-6 to M-12:

In Formulas M-1 to M-3, and Formulas M-6 to M-12, X ₁ , X ₂ and Y ₁ to Y ₁₆ are as defined in claim 1.
5. The method of claim 4,
The Y ₁ to Y ₁₆ are all C(R ₁ ), or may include 1 to 3 N, and a plurality of R ₁ are the same or different from each other.
According to claim 1,
The compound represented by Formula 1 is a compound, characterized in that it is a compound represented by any one of Formulas N-1 to N-3, and Formulas N-6 to N-12:

In Formulas N-1 to N-3, and Formulas N-6 to N-12, X ₁ , Ar ₁ and R ₁ are as defined in claim 1 .
According to claim 1,
The compound represented by Formula 1 is a compound, characterized in that it is a compound represented by any one of Formulas 3 to 7:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 3 to 7,
When Ar ₁ is plural, they are the same or different from each other, and Ar ₁ are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, or 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 ₁ ~ 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 dia It may be selected from the group consisting of a rilphosphinyl group and a C ₆ ~ C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring;
Y ₁ to Y ₁₂ are the same as or different from each other, and each independently N or C(R ₁ );
When Y ₁₃ to Y ₁₆ are a plurality, they are the same as or different from each other, and Y ₁₃ to Y ₁₆ are each independently N or C(R ₁ );
When R ₁ is a plurality, they are the same or different from each other, and R ₁ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl 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 ₁ ~ 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 It may be selected from the group consisting of an arylamine group, or combine with an adjacent group to form a condensed ring;
Ar ₁ and R ₁ of 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, an arylphosphine group, The mono or diarylphosphinyl group and the arylamine group are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl 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 ₁ ~ 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 may be unsubstituted or substituted with one or more substituents selected from the group consisting of a pinyl group and a C ₆ ~ C ₆₀ arylamine group, and when substituted with the substituent, the substituent may combine with an adjacent group to form a condensed ring And, when substituted with a plurality of substituents, they may be the same or different from each other.
8. The method of claim 7,
When the Ar _1, or wherein Ar ₁ multiple individual at least one C ₆ ~ can aryl date of C _60, and the aryl groups being substituted or unsubstituted groups of one or more C ₆ ~ C ₆₀ aryl group, a plurality of substituents When substituted, they are the same or different from each other.
8. The method of claim 7,
In Formula 4, Y ₈ is C(R ₁ ), and R ₁ is a C ₆ ~ C ₆₀ aryl group.
According to claim 1,
wherein _{at least one of R 1} and Ar ₁ to Ar ₅ is a phenyl group or a compound represented by the following formula (8):
[Formula 8]

In the formula (8),
* means a moiety bonded to Formula 1;
L ₁ is a single bond, C ₆ ~ C ₁₈ is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Z _{1 To} Z _{5 Are} the same as or different from each other, and each independently represents N or C(R ₁₁ ), wherein at least one of _{Z 1 To} Z _{5 is N;}
When R ₁₁ is a plurality, they are the same or different from each other, and R ₁₁ is 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 ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C group _{of 6} to arylboronic of C _60, C ₆ to C ₆₀ aryl phosphine group, C ₆ to C ₆₀ mono or diaryl phosphine blood group and a C ₆ - or selected from the group consisting arylsilyl of C ₆₀ of the adjacent can combine with a 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, the _{arylene group and heteroarylene group of L 1} are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C group of _40-alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl Phosphinicosuccinic consisting group and a C ₆ ~ C ₆₀ aryl silyl group of the When substituted with one or more substituents selected from the group or unsubstituted, and substituted with a plurality of substituents, they may be the same or different from each other.
11. The method of claim 10,
The substituent represented by Formula 8 is a compound, characterized in that the substituent represented by any one of the following Formulas O-1 to O-15:

In the above formulas O-1 to O-15,
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 each independently deuterium, halogen, cya. No 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, a heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Arylamine group , C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ Mono or dia A rilphosphinyl group and a C ₆ ~ C ₆₀ 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 _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 ₆₀ aryl group, heteroaryl group having 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ substituted by one substituent at least one selected from the group consisting arylsilyl of C ₆₀ unsubstituted and when substituted with a plurality of substituents, they may be the same or different from each other;
L ₁ and R ₁₁ are each as defined in claim 10 .
11. The method of claim 10,
wherein L ₁ is a single bond, a phenylene group, a biphenylene group, or a carbazolyl group.
According to claim 1,
wherein Ar ₁ to Ar ₅ are the same as or different from each other, and are each independently selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline,
Wherein Ar _{1 To} Ar ₅ Phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline are substituted or unsubstituted with one or more selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline. cyclic, and when substituted with a plurality of substituents, they are the same or different from each other.
According to claim 1,
The compound is a compound characterized in that it is selected from the group consisting of:

An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound represented by Formula 1 according to any one of claims 1 to 14.
16. The method of claim 15,
The organic material layer including the compound represented by Formula 1 is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a light emitting layer.
17. The method of claim 16,
The light emitting layer comprising the compound represented by Formula 1 is an organic electroluminescent device, characterized in that used as a phosphorescent host.