KR102444781B1 - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

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

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 compound having excellent light emitting ability and organic electroluminescence having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the compound in one or more organic material layers. It's about the little ones.

A study on organic electroluminescent devices that led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of light emission of organic thin films by Bernanose in the 1950s, was divided into functional layers of a hole layer and a light emitting layer by Tang in 1987. An organic electroluminescent device having a stacked structure has been proposed. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of a specialized material used for this.

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

The material for forming the light emitting layer of the organic electroluminescent device may be classified into blue, green, and red light emitting materials according to the light emitting 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 4 times compared to fluorescence, and thus, attention is focused on phosphorescent host materials as well as phosphorescent dopants.

As materials used for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer to date, NPB, BCP, Alq ₃ , etc. are widely known, and anthracene derivatives are reported as fluorescent dopant / host materials as light emitting materials. have. 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 a blue, green, and red dopant material. is being used as So far, CBP has shown excellent properties as a phosphorescent host material.

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

Japanese Laid-Open Patent Publication No. 2001-160489

In order to solve the above problems, an object of the present invention is to provide a novel compound that can be applied to an organic electroluminescent device and has excellent light emitting ability.

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

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

A compound represented by the following formula (1):

In Formula 1,

X is N(Ar ₂ ), O or S,

n is an integer from 0 to 2,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyl Oxy 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 Aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group,

An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, aryl of the Ar ₁ and Ar ₂ Boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ of an aryl boron group, a C ₆ ~ C ₆₀ aryl phosphine group, a C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group substituted or unsubstituted with one or more substituents selected from the group consisting of , When the substituents are plural, they may be the same as or different from each other.

In addition, the present invention includes a positive electrode, a negative electrode, and one or more organic material layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic material layers comprises a compound represented by the formula (1) An electroluminescent device is provided. Here, the organic material layer including the compound represented by Formula 1 may be selected from the group consisting 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. In this case, the compound represented by Formula 1 may be used as a phosphorescent host of the emission layer.

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, it is possible to manufacture an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer lifespan compared to a conventional host material, and furthermore, performance and lifespan This advanced full color display panel can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. Novel compounds

)의 1번 내지 4번 (또는, 5번 내지 8번) 중 어느 하나의 위치에 인돌 유도체가 결합된 구조를 기본 골격으로 하며, 이러한 기본 골격에 질소 함유 헤테로고리, 방향족고리 등 다양한 치환체가 도입되어 상기 화학식 1로 표시되는 것을 특징으로 한다. 이때, 상기 인돌 유도체로는 인돌(indol), 벤조퓨란(benzofuran), 벤조티오펜(benzothiophen)일 수 있다.The novel compound according to the present invention is carbazole (

) of 1 to 4 (or 5 to 8), the structure in which the indole derivative is bonded at any one position as the basic skeleton, and various substituents such as nitrogen-containing heterocycles and aromatic rings are introduced into this basic skeleton It is characterized in that it is represented by the above formula (1). In this case, the indole derivative may be indole, benzofuran, or benzothiophene.

The compound of Formula 1 is composed of a carbazole having a large electron donating property and an indole derivative having an electron withdrawing property, and thus has a bipolar property throughout the molecule. Since the bipolar compound represented by Formula 1 can increase the bonding force between holes and electrons, it is advantageous as a host in the phosphorescent emission layer, and can also be applied as a hole transport layer, a hole injection layer, an electron transport layer, and the like. Accordingly, the compound of Formula 1 may improve the phosphorescence properties of the organic electroluminescent device and, at the same time, improve the carrier transport ability or the luminous efficiency.

In addition, the compound of Formula 1 may control HOMO and LUMO energy levels according to the types of various substituents introduced into the basic skeleton, and may have a wide band gap as well as high carrier transport properties. In this case, when the substituent is a nitrogen-containing heterocyclic ring (eg, a pyridine group, a pyrimidine group, a quinazoline group, a triazine group, etc.), the bipolar property of the compound of Formula 1 may be further improved.

Since the compound represented by Chemical Formula 1 has a higher molecular weight than conventional materials for organic electroluminescent devices [eg, 4,4-dicarbazolybiphenyl (hereinafter, referred to as 'CBP')], the glass transition temperature is high and the thermal stability is excellent. Not only that, but the light emitting ability is excellent. Therefore, when the compound of Formula 1 is applied to the organic material layer of the organic electroluminescent device, the driving voltage, efficiency, lifespan, etc. of the device can be improved. The compound of Formula 1 may be used as an organic material layer material of an organic electroluminescent device, and preferably may be used as a light emitting layer material (blue, green and/or red phosphorescent host material).

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.

Specifically, in the compound represented by Formula 1, an indole derivative is bonded to any one of positions 1 to 4 of carbazole, and the indole derivative is indole, benzofuran, or benzothiophene ( benzothiophen). The compound of Formula 1 may be embodied as any one of Formulas 2 to 4 below.

In Formulas 2 to 4, n, Ar ₁ and Ar ₂ are each as defined in Formula 1 above.

In this case, the compound represented by Formula 1 preferably has an indole derivative bonded to the 2nd or 3rd position of the carbazole. The compound of Formula 1 may be embodied as any one of Formulas 5 to 10 below.

In Formulas 5 to 10, n, Ar ₁ and Ar ₂ are each as defined in Formula 1 above.

In addition, in the compound represented by Formula 1, it is more preferable that the indole derivative is bonded to the 3-position of the carbazole.

In the compound represented by Formula 1, when n is 0, it means that hydrogen is not substituted with a substituent. When n is an integer of 1 or 2, it means that hydrogen is substituted with phenyl or biphenyl. Preferably, n may be 0 or 1.

According to a preferred example of the present invention, Ar ₁ may be a substituent represented by the following formula (11).

In Formula 11, * means a moiety bonded to Formula 1 above.

L ₁ is a single bond, a C ₆ ~ C ₁₈ arylene group or 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 ₁ ), and when R ₁ is plural, they are the same as or different from each other.

R ₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , C 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 Aryl phosphine oxide group and C ₆ ~ C ₆₀ It may be selected from the group consisting of an arylamine group, or combined with an adjacent group to form a condensed ring.

_An alkyl group, an alkenyl group, an alkynyl 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, Aryl phosphine group, aryl phosphine oxide group and arylamine 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 alky Nyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkylox Period, 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 Aryl phosphine oxide group and C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of an arylamine group, the substituent When is plural, they may be the same or different from each other.

The substituent represented by Formula 11 may be more specific to any one of A1 to A15 below.

In A1 to A15, L ₁ and R ₁ are as defined in Formula 11 above.

p is an integer from 0 to 4. When p is 0, it means that hydrogen is not substituted with a substituent R ₂ . When p is an integer of 1 to 4, R ₂ is deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C 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 Aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group, or combined with an adjacent group to form a condensed ring, , When R ₂ is a plurality, they may be the same as or different from each other.

_An alkyl group, an alkenyl group, an alkynyl 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, Aryl phosphine group, aryl phosphine oxide group and arylamine 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 alky Nyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkylox Period, 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 Aryl phosphine oxide group and C ₆ ~ C ₆₀ May be substituted with one or more substituents selected from the group consisting of an arylamine group, wherein the substituents In the case of a plurality, they may be the same or different from each other.

According to a preferred example of the present invention, Ar ₂ is a C ₆ ~ C ₆₀ aryl group, a heteroaryl group of 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₆ ~ C ₆₀ arylsilyl group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Aryl phosphine oxide group and C ₆ ~ C ₆₀ It may be selected from the group consisting of an arylamine group. . In this case, Ar ₂ is preferably a C ₆ ~ C ₆₀ aryl group, more preferably phenyl or biphenyl.

The compound represented by Formula 1 of the present invention described above is the following compounds A-1 to A-40, B-1 to B-40, C-1 to C-40, D-1 to D-40, E -1 to E-40, F-1 to F-40, G-1 to G-40, H-1 to H-40, I-1 to I-40, J-1 to J-40, K-1 To K-40, L-1 to L-40 may be more specific to a compound represented by any one. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.

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

In the present invention, “alkenyl” refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, “alkynyl” refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples of such alkynyl include, but are not limited to, ethynyl, 2-propynyl, and the like.

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

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon 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, “aryl” means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, a form in which two or more rings are simply attached to each other or condensed 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 60 nuclear atoms. In this case, at least one carbon, preferably 1 to 3 carbons in the ring is 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, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include a linear, branched or cyclic structure. Examples of such 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, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, 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 6 to 60 carbon atoms.

In the present invention, “alkyl boron” refers to boron substituted with alkyl having 1 to 40 carbon atoms, and “aryl boron” refers to boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" means a phosphine substituted with an aryl having 6 to 60 carbon atoms, and "arylphosphine oxide group" means that the phosphine substituted with an aryl having 6 to 60 carbon atoms contains O. do.

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.

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

The compound represented by Chemical Formula 1 of the present invention as described above can be synthesized in various ways with reference to the synthesis process in Examples below.

2. Organic electric field light emitting element

The present invention provides an organic electroluminescent device comprising the compound represented by Formula 1 above.

More specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers. includes the compound represented by Formula 1 above. In this case, the compound may be used alone, or two or more may be used in combination.

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

The light emitting layer of the organic electroluminescent device of the present invention may include a host material (preferably, a phosphorescent 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 a non-limiting example 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. . In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, and preferably, the light emitting layer is represented by Formula 1 compounds may be included. Here, an electron injection layer may be additionally stacked on the electron transport layer. In addition, 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.

On the other hand, the organic electroluminescent device of the present invention can 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. have.

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 a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet may be used.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.

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

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

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

[ preparation example 1] 2-(1-phenyl-1H- indol -2- yl )-9H- carbazole synthesis

2-bromo-1-phenyl-1H-indole (50.0 g, 183.7 mmol), (9H-carbazol-2-yl)boronic acid (42.6 g, 202.1 mmol) and Pd(PPh ₃ ) ₄ (10.6 g, 9.2 mmol) ), K ₂ CO ₃ (50.7 g, 367.4 mmol) was added to 1000 ml of Toluene, 200 ml of EtOH, and 200 ml of H ₂ O, and the mixture was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound, 2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (53.9 g, yield 82%) was obtained by column chromatography.

¹ H-NMR: δ 6.80 (s, 1H), 6.87 (t, 1H), 7.20 (t, 1H), 7.35 (t, 1H), 7.50-7.63 (m, 7H), 7.74 (s, 1H), 7.91-7.94 (m, 3H), 8.19 (d, 1H), 8.31 (d, 1H), 11.66 (s, 1H)

[LCMS]: 359

[ preparation example 2] 3-(1-phenyl-1H- indol -2- yl )-9H- carbazole synthesis

2-bromo-1-phenyl-1H-indole (50.0 g, 183.7 mmol), (9H-carbazol-3-yl)boronic acid (42.6 g, 202.1 mmol) and Pd(PPh ₃ ) ₄ (10.6 g, 9.2 mmol) ), K ₂ CO ₃ (50.7 g, 367.4 mmol) was added to 1000 ml of Toluene, 200 ml of EtOH, and 200 ml of H ₂ O, and the mixture was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound 3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (52.6 g, yield 80%) was obtained by column chromatography.

¹ H-NMR: δ 6.80 (s, 1H), 6.87 (t, 1H), 7.20 (t, 1H), 7.35 (t, 1H), 7.50-7.63 (m, 7H), 7.77 (d, 1H), 7.89(s, 1H), 7.93-7.98(m, 3H), 8.19(d, 1H), 11.66(s, 1H)

[LCMS]: 359

[ preparation example 3] 2-(1,3- diphenyl -1H- indol -2- yl )-9H- carbazole synthesis

Except for using 2-bromo-1,3-diphenyl-1H-indole instead of 2-bromo-1-phenyl-1H-indole, 46.8 g of the target compound (yield 75%) ) was obtained.

¹ H-NMR: δ 7.20 (t, 1H), 7.33 (t, 1H), 7.41-7.46 (m, 4H), 7.50-7.52 (m, 5H), 7.58-7.62 (m, 4H), 7.71 (d) , 1H), 7.74(s, 1H), 7.91(d, 1H), 8.17(d, 1H), 8.19(d, 1H), 8.31(d, 1H), 11.66(s, 1H)

[LCMS]: 435

[ preparation example 4] 3-(1,3- diphenyl -1H- indol -2- yl )-9H- carbazole synthesis

Except for using 2-bromo-1,3-diphenyl-1H-indole instead of 2-bromo-1-phenyl-1H-indole, 46.8 g of the target compound (yield 75%) ) was obtained.

¹ H-NMR: δ 7.20 (t, 1H), 7.33-7.51 (m, 10H), 7.58-7.63 (m, 4H), 7.71 (d, 1H), 7.77 (d, 1H), 7.89 (s, 1H) ), 7.99 (d, 1H), 8.17 (d, 1H), 8.19 (d, 1H), 11.66 (s, 1H)

[LCMS]: 435

[ preparation example 5] 2-( benzofuran -2- yl )-9H- carbazole synthesis

57.5 g (yield 80%) of the target compound was obtained in the same manner as in [Preparation Example 1] except that 2-bromobenzofuran was used instead of 2-bromo-1-phenyl-1H-indole.

¹ H-NMR: δ 7.14(s, 1H), 7.20-7.22(m, 2H), 7.39(t, 1H), 7.50(t, 1H), 7.58-7.62(m, 3H), 7.74(s, 1H) ), 7.91 (d, 1H), 8.19 (d, 1H), 8.31 (d, 1H), 11.66 (s, 1H)

[LCMS]: 284

[ preparation example 6] 3-(3- phenylbenzofuran -2- yl )-9H- carbazole synthesis

50.6 g (yield 77%) of the target compound was obtained in the same manner as in [Preparation Example 1] except that 2-bromo-3-phenylbenzofuran was used instead of 2-bromo-1-phenyl-1H-indole.

¹ H-NMR: δ 7.20 (t, 1H), 7.31 (t, 1H), 7.39-7.46 (m, 4H), 7.50-7.54 (m, 4H), 7.63 (d, 1H), 7.77 (s, 1H) ), 7.89(s, 1H), 7.98-7.99(m, 2H), 8.19(d, 1H), 11.66(s, 1H)

[LCMS]: 360

[ preparation example 7] 2-( benzo[b]thiophen -2- yl )-9H- carbazole synthesis

52.6 g (yield 75%) of the target compound was obtained in the same manner as in [Preparation Example 1] except that 2-bromobenzo[b]thiophene was used instead of 2-bromo-1-phenyl-1H-indole.

¹ H-NMR: δ 7.20 (t, 1H), 7.32 (t, 1H), 7.49-7.50 (m, 2H), 7.59 (s, 1H), 7.63 (d, 1H), 7.74 (s, 1H), 7.79 (d, 1H), 7.91 (d, 1H), 7.93 (d, 1H), 8.19 (d, 1H), 8.31 (d, 1H), 11.66 (s, 1H)

[LCMS] : 300

[ preparation example 8] 3-(3- phenylbenzo[b]thiophen -2- yl )-9H- carbazole synthesis

45.4 g (yield 70%) of the target compound was prepared in the same manner as in [Preparation Example 1] except that 2-bromo-3-phenylbenzo[b]thiophene was used instead of 2-bromo-1-phenyl-1H-indole. got it

¹ H-NMR: δ 7.20 (t, 1H), 7.41-7.63 (m, 9H), 7.77 (d, 1H), 7.89 (s, 1H), 7.93 (d, 1H), 7.99 (d, 1H), 8.19 (d, 1H), 8.45 (d, 1H), 11.66 (s, 1H)

[LCMS]: 376

[ preparation example 9] 3-( benzofuran -2- yl )-9H- carbazole synthesis

57.5 g (yield 80%) of the target compound was obtained in the same manner as in [Preparation Example 2] except that 2-bromobenzofuran was used instead of 2-bromo-1-phenyl-1H-indole.

¹ H-NMR: δ 7.14(s, 1H), 7.20-7.22(m, 2H), 7.39(t, 1H), 7.50-7.63(m, 4H), 7.77(d, 1H), 7.89(s, 1H) ), 7.99 (d, 1H), 8.19 (d, 1H), 11.66 (s, 1H)

[LCMS]: 284

[ preparation example 10] 3-(3- phenylbenzofuran -2- yl )-9H- carbazole synthesis

50.6 g (yield 77%) of the target compound was obtained in the same manner as in [Preparation Example 2] except that 2-bromo-3-phenylbenzofuran was used instead of 2-bromo-1-phenyl-1H-indole.

¹ H-NMR: δ 7.20 (t, 1H), 7.31 (t, 1H), 7.39-7.63 (m, 9H), 7.77 (d, 1H), 7.89 (s, 1H), 7.98-7.99 (m, 2H) ), 8.19 (d, 1H), 11.66 (s, 1H)

[LCMS]: 360

[ preparation example 11] 3-( benzo[b]thiophen -2- yl )-9H- carbazole synthesis

52.6 g (yield 75%) of the target compound was obtained in the same manner as in [Preparation Example 2] except that 2-bromobenzo[b]thiophene was used instead of 2-bromo-1-phenyl-1H-indole.

¹ H-NMR: δ 7.20 (t, 1H), 7.32 (t, 1H), 7.49-7.50 (m, 2H), 7.59 (s, 1H), 7.63 (d, 1H), 7.77 (d, 1H), 7.79(d, 1H), 7.89(s, 1H), 7.93(d, 1H), 7.99(d, 1H), 8.19(d, 1H), 11.66(s, 1H)

[LCMS] : 300

[ preparation example 12] 3-(3- phenylbenzo[b]thiophen -2- yl )-9H- carbazole synthesis

Except for using 2-bromo-3-phenylbenzo[b]thiophene instead of 2-bromo-1-phenyl-1H-indole, 45.4 g (yield 70%) of the target compound was prepared in the same manner as in [Preparation Example 2]. got it

¹ H-NMR: δ 7.20 (t, 1H), 7.41-7.56 (m, 8H), 7.63 (d, 1H), 7.77 (d, 1H), 7.89 (s, 1H), 7.93 (d, 1H), 7.99 (d, 1H), 8.19 (d, 1H), 8.45 (d, 1H), 11.66 (s, 1H)

[LCMS]: 376

[ Synthesis example 1] Synthesis of compound A-2

2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 1 and 2-([1,1'-biphenyl]-4-yl)-4- chloro-6-phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound A-2 (6.5 g, yield 70%) was obtained by column chromatography.

[LCMS]: 666

[ Synthesis example 2] Synthesis of compound A-8

2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 1 and 2-chloro-4-(dibenzo[b,d]furan-3-yl) -6-phenyl-1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound A-8 (6.9 g, yield 73%) was obtained by column chromatography.

[LCMS]: 680

[ Synthesis example 3] Synthesis of compound A-11

2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl) of Preparation Example 1 -6-phenyl-1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound A-11 (7.0 g, yield 72%) was obtained by column chromatography.

[LCMS] : 696

[ Synthesis example 4] Synthesis of compound A-18

2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 1 and 2-([1,1'-biphenyl]-4-yl)-4- chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), ( t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound A-18 (7.6 g, yield 70%) was obtained by column chromatography.

[LCMS]: 782

[ Synthesis example 5] Synthesis of compound A-20

2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 1 and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl) )phenyl)pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) ) was added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound A-20 (6.0 g, yield 65%) was obtained by column chromatography.

[LCMS]: 666

[ Synthesis example 6] Synthesis of compound A-21

2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 1 and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5 -triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) It was put into 100ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound A-21 (6.8 g, yield 73%) was obtained by column chromatography.

[LCMS]: 666

[ Synthesis example 7] Synthesis of compound A-27

2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 1 and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan- 4-yl)-6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound A-27 (7 g, yield 70%) was obtained by column chromatography.

[LCMS]: 756

[ Synthesis example 8] Synthesis of compound A-39

2-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 1 and 4-([1,1'-biphenyl]-4-yl)-6- (3-chlorophenyl)-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu ( 2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound A-39 (7 g, yield 68%) was obtained by column chromatography.

[LCMS]: 756

[ Synthesis example 9] Synthesis of compound B-2

3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 2 and 2-([1,1'-biphenyl]-4-yl)-4- chloro-6-phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound B-2 (6.5 g, yield 70%) was obtained by column chromatography.

[LCMS]: 666

[ Synthesis example 10] Synthesis of compound B-8

3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl) of Preparation Example 2 -6-phenyl-1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound B-8 (6.9 g, yield 73%) was obtained by column chromatography.

[LCMS]: 680

[ Synthesis example 11] Synthesis of compound B-11

3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl) of Preparation Example 2 -6-phenyl-1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound B-11 (7.0 g, yield 72%) was obtained by column chromatography.

[LCMS] : 696

[ Synthesis example 12] Synthesis of compound B-18

3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 2 and 2-([1,1'-biphenyl]-4-yl)-4- chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), ( t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound B-18 (7.6 g, yield 70%) was obtained by column chromatography.

[LCMS]: 782

[ Synthesis example 13] Synthesis of compound B-20

3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 2 and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl) )phenyl)pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) ) was added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound B-20 (6.0 g, yield 65%) was obtained by column chromatography.

[LCMS]: 666

[ Synthesis example 14] Synthesis of compound B-21

3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5 of Preparation Example 2 -triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) It was put into 100ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound B-21 (6.8 g, yield 73%) was obtained by column chromatography.

[LCMS]: 666

[ Synthesis example 15] Synthesis of compound B-27

3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 2 and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan- 4-yl)-6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound B-27 (7 g, yield 70%) was obtained by column chromatography.

[LCMS]: 756

[ Synthesis example 16] Synthesis of compound B-39

3-(1-phenyl-1H-indol-2-yl)-9H-carbazole (5 g, 13.9 mmol) of Preparation Example 2 and 4-([1,1'-biphenyl]-4-yl)-6- (3-chlorophenyl)-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu ( 2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound B-39 (7 g, yield 68%) was obtained by column chromatography.

[LCMS]: 756

[ Synthesis example 17] Synthesis of compound C-2

2-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) and 2-([1,1'-biphenyl]-4-yl)- of Preparation Example 3 4-chloro-6-phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) ), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C-2 (7.2 g, yield 70%) was obtained by column chromatography.

[LCMS]: 742

[ Synthesis example 18] Synthesis of compound C-8

2-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) of Preparation Example 3 and 2-chloro-4-(dibenzo[b,d]furan-3- yl)-6-phenyl-1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) , NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C-8 (7.0 g, yield 67%) was obtained by column chromatography.

[LCMS]: 756

[ Synthesis example 19] Synthesis of compound C-11

2-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) of Preparation Example 3 and 2-chloro-4-(dibenzo[b,d]thiophen-4- yl)-6-phenyl-1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) , NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C-11 (7.0 g, yield 65%) was obtained by column chromatography.

[LCMS]: 772

[ Synthesis example 20] Synthesis of compound C-18

2-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) and 2-([1,1'-biphenyl]-4-yl)- of Preparation Example 3 4-chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol) , (t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C-18 (8.3 g, yield 70%) was obtained by column chromatography.

[LCMS]: 859

[ Synthesis example 21] Synthesis of compound C-20

2- (1,3-diphenyl-1H-indol-2-yl) -9H-carbazole (6 g, 13.9 mmol) of Preparation Example 3 and 4-chloro-2-phenyl-6- (4- (pyridin-3) -yl)phenyl)pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C-20 (6.7 g, yield 65%) was obtained by column chromatography.

[LCMS]: 742

[ Synthesis example 22] Synthesis of compound C-21

2-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3 of Preparation Example 3 ,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) ) was added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C-21 (7.3 g, yield 71%) was obtained by column chromatography.

[LCMS]: 742

[ Synthesis example 23] Synthesis of compound C-27

2-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) of Preparation Example 3 and 2-(3-chlorophenyl)-4-(dibenzo[b,d] furan-4-yl)-6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g , 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C-27 (7.7 g, yield 67%) was obtained by column chromatography.

[LCMS]: 832

[ Synthesis example 24] Synthesis of compound C-39

2-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) and 4-([1,1'-biphenyl]-4-yl)- of Preparation Example 3 6-(3-chlorophenyl)-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt- Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound C-39 (7.3 g, yield 64%) was obtained by column chromatography.

[LCMS]: 818

[ Synthesis example 25] Synthesis of compound D-2

3-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) and 2-([1,1'-biphenyl]-4-yl)- of Preparation Example 4 4-chloro-6-phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) ), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound D-2 (7.2 g, yield 70%) was obtained by column chromatography.

[LCMS]: 742

[ Synthesis example 26] Synthesis of compound D-8

3-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) of Preparation Example 4 and 2-chloro-4-(dibenzo[b,d]furan-3- yl)-6-phenyl-1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) , NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound D-8 (7.0 g, yield 67%) was obtained by column chromatography.

[LCMS]: 756

[ Synthesis example 27] Synthesis of compound D-11

3-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) of Preparation Example 4 and 2-chloro-4-(dibenzo[b,d]thiophen-4- yl)-6-phenyl-1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) , NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound D-11 (7.0 g, yield 65%) was obtained by column chromatography.

[LCMS]: 772

[ Synthesis example 28] Synthesis of compound D-18

3-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) and 2-([1,1'-biphenyl]-4-yl)- of Preparation Example 4 4-chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol) , (t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound D-18 (8.3 g, yield 70%) was obtained by column chromatography.

[LCMS]: 859

[ Synthesis example 29] Synthesis of compound D-20

3-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) of Preparation Example 4 and 4-chloro-2-phenyl-6-(4-(pyridin-3) -yl)phenyl)pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound D-20 (6.7 g, yield 65%) was obtained by column chromatography.

[LCMS]: 742

[ Synthesis example 30] Synthesis of compound D-21

3-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3 of Preparation Example 4 ,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) ) was added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound D-21 (7.3 g, yield 71%) was obtained by column chromatography.

[LCMS]: 742

[ Synthesis example 31] Synthesis of compound D-27

3-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) of Preparation Example 4 and 2-(3-chlorophenyl)-4-(dibenzo[b,d] furan-4-yl)-6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g , 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound D-27 (7.7 g, yield 67%) was obtained by column chromatography.

[LCMS]: 832

[ Synthesis example 32] Synthesis of compound D-39

3-(1,3-diphenyl-1H-indol-2-yl)-9H-carbazole (6 g, 13.9 mmol) and 4-([1,1'-biphenyl]-4-yl)- of Preparation Example 4 6-(3-chlorophenyl)-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt- Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound D-39 (7.3 g, yield 64%) was obtained by column chromatography.

[LCMS]: 818

[ Synthesis example 33] Synthesis of compound E-2

2-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) of Preparation Example 5 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl- 1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g) , 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound E-2 (6.2 g, yield 75%) was obtained by column chromatography.

[LCMS]: 591

[ Synthesis example 34] Synthesis of compound E-8

2-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1 of Preparation Example 5 ,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound E-8 (6.1 g, yield 72%) was obtained by column chromatography.

[LCMS]: 605

[ Synthesis example 35] Synthesis of compound E-11

2-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1 of Preparation Example 5 ,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound E-11 (5.7 g, yield 66%) was obtained by column chromatography.

[LCMS]: 621

[ Synthesis example 36] Synthesis of compound E-18

2-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) of Preparation Example 5 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(9 ,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3g, 1.4mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound E-18 (6.7 g, yield 76%) was obtained by column chromatography.

[LCMS]: 707

[ Synthesis example 37] Synthesis of compound E-20

2-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) of Preparation Example 5 and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of Toluene. It was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound E-20 (5.6 g, yield 68%) was obtained by column chromatography.

[LCMS]: 591

[ Synthesis example 38] Synthesis of compound E-21

2-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), and NaOt-Bu (2.7 g, 27.9 mmol) in 100 ml of Toluene for 12 hours It was heated and refluxed for a while. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound E-21 (5.7 g, yield 70%) was obtained by column chromatography.

[LCMS]: 591

[ Synthesis example 39] Synthesis of compound E-27

2-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6 of Preparation Example 5 -phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound E-27 (5.8 g, yield 62%) was obtained by column chromatography.

[LCMS]: 681

[ Synthesis example 40] Synthesis of compound E-39

2-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)- of Preparation Example 5 2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound E-39 (6.2 g, yield 67%) was obtained by column chromatography.

[LCMS]: 666

[ Synthesis example 41] Synthesis of compound F-2

2-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) of Preparation Example 6 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6- phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu ( 2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound F-2 (7.2 g, yield 78%) was obtained by column chromatography.

[LCMS]: 667

[ Synthesis example 42] Synthesis of compound F-8

2-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl of Preparation Example 6 -1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound F-8 (6.8 g, yield 72%) was obtained by column chromatography.

[LCMS]: 681

[ Synthesis example 43] Synthesis of compound F-11

2-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl of Preparation Example 6 -1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound F-11 (6.7 g, yield 69%) was obtained by column chromatography.

[LCMS]: 697

[ Synthesis example 44] Synthesis of compound F-18

2-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) of Preparation Example 6 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6- (9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) 3P (0.3g, _1.4mmol ), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100ml of Toluene, and the mixture was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound F-18 (6.9 g, yield 64%) was obtained by column chromatography.

[LCMS]: 783

[ Synthesis example 45] Synthesis of compound F-20

2-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine of Preparation Example 6 (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) in 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound F-20 (6.2 g, yield 67%) was obtained by column chromatography.

[LCMS]: 667

[ Synthesis example 46] Synthesis of compound F-21

2-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of Toluene. It was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound F-21 (6.6 g, yield 71%) was obtained by column chromatography.

[LCMS]: 667

[ Synthesis example 47] Synthesis of compound F-27

2-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl) of Preparation Example 6 -6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound F-27 (6.9 g, yield 66%) was obtained by column chromatography.

[LCMS] : 757

[ Synthesis example 48] Synthesis of compound F-39

2-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) of Preparation Example 6 and 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl )-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9) mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound F-39 (7.0 g, yield 68%) was obtained by column chromatography.

[LCMS]: 742

[ Synthesis example 49] Synthesis of compound G-2

2-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 7 and 2-([1,1'-biphenyl]-4-yl)-4-chloro- 6-phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt- Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound G-2 (6.3 g, yield 75%) was obtained by column chromatography.

[LCMS]: 607

[ Synthesis example 50] Synthesis of compound G-8

2-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6 of Preparation Example 7 -phenyl-1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound G-8 (6.2 g, yield 72%) was obtained by column chromatography.

[LCMS]: 621

[ Synthesis example 51] Synthesis of compound G-11

2-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6 of Preparation Example 7 -phenyl-1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound G-11 (5.8 g, yield 66%) was obtained by column chromatography.

[LCMS]: 637

[ Synthesis example 52] Synthesis of compound G-18

2-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 7 and 2-([1,1'-biphenyl]-4-yl)-4-chloro- 6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t- Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene, and the mixture was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound G-18 (7.6 g, yield 76%) was obtained by column chromatography.

[LCMS] : 723

[ Synthesis example 53] Synthesis of compound G-20

2-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 7 and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl )pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) It was put into 100ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound G-20 (5.7 g, yield 68%) was obtained by column chromatography.

[LCMS]: 607

[ Synthesis example 54] Synthesis of compound G-21

2-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine of Preparation Example 7 (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) in 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound G-21 (5.9 g, yield 70%) was obtained by column chromatography.

[LCMS]: 607

[ Synthesis example 55] Synthesis of compound G-27

2-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4- of Preparation Example 7 yl)-6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) , NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound G-27 (6.0 g, yield 62%) was obtained by column chromatography.

[LCMS]: 697

[ Synthesis example 56] Synthesis of compound G-39

2-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 7 and 4-([1,1'-biphenyl]-4-yl)-6-(3 -chlorophenyl)-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g) , 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound G-39 (6.3 g, yield 67%) was obtained by column chromatography.

[LCMS]: 682

[ Synthesis example 57] Synthesis of compound H-2

2-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) of Preparation Example 8 and 2-([1,1'-biphenyl]-4-yl)-4- chloro-6-phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound H-2 (7.4 g, yield 78%) was obtained by column chromatography.

[LCMS]: 683

[ Synthesis example 58] Synthesis of compound H-8

2-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl) of Preparation Example 8 -6-phenyl-1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound H-8 (6.9 g, yield 72%) was obtained by column chromatography.

[LCMS]: 697

[ Synthesis example 59] Synthesis of compound H-11

2-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl) of Preparation Example 8 -6-phenyl-1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound H-11 (6.8 g, yield 69%) was obtained by column chromatography.

[LCMS] : 713

[ Synthesis example 60] Synthesis of compound H-18

2-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) of Preparation Example 8 and 2-([1,1'-biphenyl]-4-yl)-4- chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), ( t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound H-18 (7.1 g, yield 64%) was obtained by column chromatography.

[LCMS] : 800

[ Synthesis example 61] Synthesis of compound H-20

2-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) of Preparation Example 8 and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl) )phenyl)pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) ) was added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound H-20 (6.0 g, yield 64%) was obtained by column chromatography.

[LCMS]: 683

[ Synthesis example 62] Synthesis of compound H-21

2-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5 of Preparation Example 8 -triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) It was put into 100ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound H-21 (6.7 g, yield 71%) was obtained by column chromatography.

[LCMS]: 683

[ Synthesis example 63] Synthesis of compound H-27

2-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan- 4-yl)-6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound H-27 (7.0 g, yield 66%) was obtained by column chromatography.

[LCMS] : 773

[ Synthesis example 64] Synthesis of compound H-39

2-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) of Preparation Example 8 and 4-([1,1'-biphenyl]-4-yl)-6- (3-chlorophenyl)-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu ( 2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound H-39 (7.1 g, yield 68%) was obtained by column chromatography.

[LCMS] : 758

[ Synthesis example 65] Synthesis of compound I-2

3-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl- of Preparation Example 9 1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g) , 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound I-2 (6.2 g, yield 75%) was obtained by column chromatography.

[LCMS]: 591

[ Synthesis example 66] Synthesis of compound I-8

3-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1 of Preparation Example 9 ,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound I-8 (6.1 g, yield 72%) was obtained by column chromatography.

[LCMS]: 605

[ Synthesis example 67] Synthesis of compound I-11

3-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1 of Preparation Example 9 ,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound I-11 (5.7 g, yield 66%) was obtained by column chromatography.

[LCMS]: 621

[ Synthesis example 68] Synthesis of compound I-18

3-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) of Preparation 9 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(9 ,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3g, 1.4mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound I-18 (6.7 g, yield 76%) was obtained by column chromatography.

[LCMS]: 707

[ Synthesis example 69] Synthesis of compound I-20

3-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of Toluene. It was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound I-20 (5.6 g, yield 68%) was obtained by column chromatography.

[LCMS]: 591

[ Synthesis example 70] Synthesis of compound I-21

3-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), and NaOt-Bu (2.7 g, 27.9 mmol) in 100 ml of Toluene for 12 hours It was heated and refluxed for a while. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound I-21 (5.7 g, yield 70%) was obtained by column chromatography.

[LCMS]: 591

[ Synthesis example 71] Synthesis of compound I-27

3-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6 of Preparation Example 9 -phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound I-27 (5.8 g, yield 62%) was obtained by column chromatography.

[LCMS]: 681

[ Synthesis example 72] Synthesis of compound I-39

3-(benzofuran-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)- of Preparation Example 9 2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound I-39 (6.2 g, yield 67%) was obtained by column chromatography.

[LCMS]: 666

[ Synthesis example 73] Synthesis of compound J-2

3-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) of Preparation 10 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6- phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu ( 2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound J-2 (7.2 g, yield 78%) was obtained by column chromatography.

[LCMS]: 667

[ Synthesis example 74] Synthesis of compound J-8

3-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) of Preparation 10 and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl -1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound J-8 (6.8 g, yield 72%) was obtained by column chromatography.

[LCMS]: 681

[ Synthesis example 75] Synthesis of compound J-11

3-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) of Preparation 10 and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl -1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound J-11 (6.7 g, yield 69%) was obtained by column chromatography.

[LCMS]: 697

[ Synthesis example 76] Synthesis of compound J-18

3-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) of Preparation 10 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6- (9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) 3P (0.3g, _1.4mmol ), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100ml of Toluene, and the mixture was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound J-18 (6.9 g, yield 64%) was obtained by column chromatography.

[LCMS]: 783

[ Synthesis example 77] Synthesis of compound J-20

3-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine of Preparation Example 10 (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) in 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound J-20 (6.2 g, yield 67%) was obtained by column chromatography.

[LCMS]: 667

[ Synthesis example 78] Synthesis of compound J-21

3-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of Toluene. It was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound J-21 (6.6 g, yield 71%) was obtained by column chromatography.

[LCMS]: 667

[ Synthesis example 79] Synthesis of compound J-27

3-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl) of Preparation Example 10 -6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound J-27 (6.9 g, yield 66%) was obtained by column chromatography.

[LCMS] : 757

[ Synthesis example 80] Synthesis of compound J-39

3-(3-phenylbenzofuran-2-yl)-9H-carbazole (5.0 g, 13.9 mmol) of Preparation 10 and 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl )-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9) mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound J-39 (7.0 g, yield 68%) was obtained by column chromatography.

[LCMS]: 742

[ Synthesis example 81] Synthesis of compound K-2

3-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 11 and 2-([1,1'-biphenyl]-4-yl)-4-chloro- 6-phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt- Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound K-2 (6.3 g, yield 75%) was obtained by column chromatography.

[LCMS]: 607

[ Synthesis example 82] Synthesis of compound K-8

3-(benzo[b]thiophen-2-yl)-9H-carbazole (3.5 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6 of Preparation Example 11 -phenyl-1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound K-8 (6.2 g, yield 72%) was obtained by column chromatography.

[LCMS]: 621

[ Synthesis example 83] Synthesis of compound K-11

3-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6 of Preparation Example 11 -phenyl-1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound K-11 (5.8 g, yield 66%) was obtained by column chromatography.

[LCMS]: 637

[ Synthesis example 84] Synthesis of compound K-18

3-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 11 and 2-([1,1'-biphenyl]-4-yl)-4-chloro- 6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t- Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene, and the mixture was heated and refluxed for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound K-18 (7.6 g, yield 76%) was obtained by column chromatography.

[LCMS] : 723

[ Synthesis example 85] Synthesis of compound K-20

3-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 11 and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl )pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) It was put into 100ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound K-20 (5.7 g, yield 68%) was obtained by column chromatography.

[LCMS]: 607

[ Synthesis example 86] Synthesis of compound K-21

3-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine of Preparation Example 11 (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) in 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound K-21 (5.9 g, yield 70%) was obtained by column chromatography.

[LCMS]: 607

[ Synthesis example 87] Synthesis of compound K-27

3-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 11 and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4- yl)-6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) , NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound K-27 (6.0 g, yield 62%) was obtained by column chromatography.

[LCMS]: 697

[ Synthesis example 88] Synthesis of compound K-39

3-(benzo[b]thiophen-2-yl)-9H-carbazole (4.2 g, 13.9 mmol) of Preparation Example 11 and 4-([1,1'-biphenyl]-4-yl)-6-(3 -chlorophenyl)-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g) , 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound K-39 (6.3 g, yield 67%) was obtained by column chromatography.

[LCMS]: 682

[ Synthesis example 89] Synthesis of compound L-2

3-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- of Preparation Example 12 chloro-6-phenyl-1,3,5-triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound L-2 (7.4 g, yield 78%) was obtained by column chromatography.

[LCMS]: 683

[ Synthesis example 90] Synthesis of compound L-8

3-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl) of Preparation Example 12 -6-phenyl-1,3,5-triazine (5.5 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound L-8 (6.9 g, yield 72%) was obtained by column chromatography.

[LCMS]: 697

[ Synthesis example 91] Synthesis of compound L-11

3-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl) of Preparation Example 12 -6-phenyl-1,3,5-triazine (5.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt -Bu (2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound L-11 (6.8 g, yield 69%) was obtained by column chromatography.

[LCMS] : 713

[ Synthesis example 92] Synthesis of compound L-18

3-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- of Preparation Example 12 chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (7.1 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), ( t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound L-18 (7.1 g, yield 64%) was obtained by column chromatography.

[LCMS] : 800

[ Synthesis example 93] Synthesis of compound L-20

3-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) of Preparation Example 12 and 4-chloro-2-phenyl-6-(4-(pyridin-3-yl) )phenyl)pyrimidine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) ) was added to 100 ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound L-20 (6.0 g, yield 64%) was obtained by column chromatography.

[LCMS]: 683

[ Synthesis example 94] Synthesis of compound L-21

3-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5 of Preparation Example 12 -triazine (5.3 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu (2.7 g, 27.9 mmol) It was put into 100ml of toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound L-21 (6.7 g, yield 71%) was obtained by column chromatography.

[LCMS]: 683

[ Synthesis example 95] Synthesis of compound L-27

3-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) of Preparation 12 and 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan- 4-yl)-6-phenyl-1,3,5-triazine (6.7 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol) and NaOt-Bu (2.7 g, 27.9 mmol) were added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound L-27 (7.0 g, yield 66%) was obtained by column chromatography.

[LCMS] : 773

[ Synthesis example 96] Synthesis of compound L-39

3-(3-phenylbenzo[b]thiophen-2-yl)-9H-carbazole (5.2 g, 13.9 mmol) and 4-([1,1'-biphenyl]-4-yl)-6- of Preparation Example 12 (3-chlorophenyl)-2-phenylpyrimidine (6.4 g, 15.3 mmol) and Pd ₂ (dba) ₃ (0.6 g, 0.7 mmol), (t-Bu) ₃ P (0.3 g, 1.4 mmol), NaOt-Bu ( 2.7 g, 27.9 mmol) was added to 100 ml of Toluene and heated to reflux for 12 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto and filtered. After removing the solvent of the filtered organic layer, the target compound L-39 (7.1 g, yield 68%) was obtained by column chromatography.

[LCMS] : 758

[ Example 1 to 96] green organic electric field Fabrication of light emitting devices

Compounds A-2, A-8, A-11, A-18, A-20, A-21, A-27, A-39, B-2, B-8, B-11 synthesized in the above synthesis example , B-18, B-20, B-21, B-27, B-39, C-2, C-8, C-11, C-18, C-20, C-21, C-27, C -39, D-2, D-8, D-11, D-18, D-20, D-21, D-27, D-39, E-2, E-8, E-11, E-18 , E-20, E-21, E-27, E-39, F-2, F-8, F-11, F-18, F-20, F-21, F-27, F-39, G -2, G-8, G-11, G-18, G-20, G-21, G-27, G-39, H-2, H-8, H-11, H-18, H-20 , H-21, H-27, H-39, I-2, I-8, I-11, I-18, I-20, I-21, I-27, I-39, J-2, J -8, J-11, J-18, J-20, J-21, J-27, J-39, K-2, K-8, K-11, K-18, K-20, K-21 , K-27, K-39, L-2, L-8, L-11, L-18, L-20, L-21, L-27, L-39 high-purity sublimation purification by a commonly known method After that, a green 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 ultrasonically cleaned with distilled water. 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), washed for 5 minutes using UV, and coated with a vacuum evaporator The substrate was transferred.

On the thus prepared ITO transparent glass substrate (electrode), m-MTDATA (60 nm)/TCTA (80 nm)/ 90% of the compound of the above synthesis example + 10% of Ir(ppy) ₃ (30 nm)/BCP (10 nm)/ Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate a green organic electroluminescent device.

[ comparative example 1] Green Organic electric field Fabrication of light emitting devices

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

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , CBP and BCP used in Examples 1 to 96 and Comparative Example 1 are as follows.

[ evaluation example One]

For each green organic electroluminescent device manufactured in Examples 1 to 96 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. .

Sample host Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 A-2 4.3 458 54.0 Example 2 A-8 3.6 457 59.5 Example 3 A-11 3.8 458 56.5 Example 4 A-18 3.8 459 58.3 Example 5 A-20 3.7 459 59.3 Example 6 A-21 3.7 457 57.0 Example 7 A-27 3.9 458 59.1 Example 8 A-39 3.9 459 57.0 Example 9 B-2 4.0 458 55.9 Example 10 B-8 3.6 458 60.0 Example 11 B-11 4.1 458 54.8 Example 12 B-18 3.8 459 60.5 Example 13 B-20 3.7 458 57.7 Example 14 B-21 4.1 458 57.0 Example 15 B-27 3.8 458 59.1 Example 16 B-39 4.1 458 57.0 Example 17 C-2 3.8 458 59.1 Example 18 C-8 3.9 458 58.0 Example 19 C-11 3.6 458 60.0 Example 20 C-18 3.8 457 58.8 Example 21 C-20 3.8 458 54.0 Example 22 C-21 3.7 457 59.5 Example 23 C-27 3.8 458 56.5 Example 24 C-39 3.8 459 55.2 Example 25 D-2 3.7 459 54.8 Example 26 D-8 3.7 457 60.5 Example 27 D-11 3.9 458 57.7 Example 28 D-18 3.9 459 58.6 Example 29 D-20 4.0 458 55.9 Example 30 D-21 3.8 457 58.5 Example 31 D-27 3.8 458 59.1 Example 32 D-39 3.7 458 60.0 Example 33 E-2 3.9 458 58.0 Example 34 E-8 3.7 458 60.0 Example 35 E-11 3.6 457 58.8 Example 36 E-18 4.3 458 54.0 Example 37 E-20 3.8 458 59.1 Example 38 E-21 3.9 458 58.0 Example 39 E-27 3.7 458 60.0 Example 40 E-39 3.6 457 58.8 Example 41 F-2 4.3 458 54.0 Example 42 F-8 3.6 457 59.5 Example 43 F-11 3.8 458 56.5 Example 44 F-18 3.8 459 55.2 Example 45 F-20 3.7 459 54.8 Example 46 F-21 3.7 457 60.5 Example 47 F-27 3.9 458 57.7 Example 48 F-39 3.9 459 58.6 Example 49 G-2 4.0 458 55.9 Example 50 G-8 3.6 458 60.0 Example 51 G-11 4.1 458 57.9 Example 52 G-18 3.8 459 58.3 Example 53 G-20 3.7 458 59.3 Example 54 G-21 4.1 458 57.0 Example 55 G-27 3.8 458 59.1 Example 56 G-39 4.1 458 57.0 Example 57 H-2 3.8 458 59.1 Example 58 H-8 3.9 458 58.0 Example 59 H-11 3.7 458 60.0 Example 60 H-18 3.6 457 58.8 Example 61 H-20 4.3 458 54.0 Example 62 H-21 3.6 457 59.5 Example 63 H-27 3.8 458 56.5 Example 64 H-39 3.8 459 55.2 Example 65 I-2 3.7 459 54.8 Example 66 I-8 3.7 457 60.5 Example 67 I-11 3.9 458 57.7 Example 68 I-18 3.9 459 58.6 Example 69 I-20 4.0 458 55.9 Example 70 I-21 3.8 457 58.5 Example 71 I-27 3.8 458 59.1 Example 72 I-39 3.7 458 54.8 Example 73 J-2 3.9 458 60.5 Example 74 J-8 3.7 458 57.7 Example 75 J-11 3.6 457 58.6 Example 76 J-18 4.3 458 55.9 Example 77 J-20 3.8 458 59.1 Example 78 J-21 3.9 458 58.0 Example 79 J-27 3.7 458 60.0 Example 80 J-39 3.6 457 58.8 Example 81 K-2 4.1 458 57.9 Example 82 K-8 3.8 459 58.3 Example 83 K-11 3.7 458 59.3 Example 84 K-18 4.1 458 57.0 Example 85 K-20 3.8 458 59.1 Example 86 K-21 4.1 458 57.0 Example 87 K-27 3.8 458 59.1 Example 88 K-39 3.7 458 58.0 Example 89 L-2 4.1 458 60.0 Example 90 L-8 3.8 457 58.8 Example 91 L-11 4.3 458 54.0 Example 92 L-18 3.6 457 59.5 Example 93 L-20 3.8 458 56.5 Example 94 L-21 3.8 459 55.2 Example 95 L-27 3.7 459 54.8 Example 96 L-39 3.7 457 60.5 Comparative Example 1 CBP 5.5 459 44.2

As shown in Table 1, the green organic electroluminescent device (Examples 1 to 96) using the compound according to the present invention in the light emitting layer has a current efficiency compared to the green organic electroluminescent device (Comparative Example 1) in which the conventional CBP is applied to the light emitting layer. and excellent driving voltage.

Claims (8)

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

In Formula 1,
X is N(Ar ₂ ), O or S,
n is an integer from 0 to 2,
Ar1 is represented by the following formula (11),
[Formula 11]

In the above formula (11),
* means a moiety bonded to Formula 1,
L1 is a single bond, a C6~ C18 arylene group or a heteroarylene group having 5 to 18 nuclear atoms,
Z1 to Z5 are the same or different from each other, and each independently represent N or C(R1), and when R1 is plural, they are the same as or different from each other,
R1 is hydrogen, deuterium, halogen, cyano group, nitro group, C1~ C40 alkyl group, C2~ C40 alkenyl group, C2~ C40 alkynyl group, C3~ C40 cycloalkyl group, heterocyclo having 3 to 40 nuclear atoms Alkyl group, C6~ C60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C1~ C40 alkyloxy group, C6~ C60 aryloxy group, C1~ C40 alkylsilyl group, C6~ C60 arylsilyl group, C1~ C40 alkyl boron group, C6~ C60 aryl boron group, C6~ C60 arylphosphine group, C6~ C60 arylphosphine oxide group and C6~ C60 arylamine group (provided that , when R1 is 3, except when only two R1s are hydrogen or deuterium),
R1 is an alkyl group, an alkenyl group, an alkynyl 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 aryl group The phosphine group, the arylphosphine oxide group and the arylamine group are each independently deuterium, halogen, cyano group, nitro group, C1~ C40 alkyl group, C2~ C40 alkenyl group, C2~ C40 alkynyl group, C3~ C40 cyclo Alkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6 to C60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C1 to C40 alkyloxy group, C6 to C60 aryloxy group, C1 to C40 of Alkylsilyl group, C6~ C60 Arylsilyl group, C1~ C40 Alkyl boron group, C6~ C60 Aryl boron group, C6~ C60 Aryl phosphine group, C6~ C60 Aryl phosphine oxide group and C6~ C60 substituted or unsubstituted with one or more substituents selected from the group consisting of an arylamine group of
Ar ₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , C 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 An aryl phosphine oxide group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group,
_An alkyl group, an alkenyl group, an alkynyl group, 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, Aryl phosphine group, aryl phosphine oxide group and arylamine 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 alky Nyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkylox Period, 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 Aryl phosphine oxide group and C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of an arylamine group, the substituent When is plural, they may be the same or different from each other. According to claim 1,
The compound represented by Formula 1 is a compound represented by one of Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,
n, Ar ₁ and Ar ₂ are each as defined in claim 1. According to claim 1,
The compound represented by Formula 1 is a compound represented by one of Formulas 5 to 10:
[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 5 to 10,
n, Ar ₁ and Ar ₂ are each as defined in claim 1. delete According to claim 1,
The substituent represented by Formula 11 is a compound selected from the group consisting of the following Formulas A1 to A9.

In A1 to A9,
L ₁ and R ₁ are as defined in claim 1. An anode, a cathode, and one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 3 and 5. 7. The method of claim 6,
The organic material layer containing the compound is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer. 8. The method of claim 7,
The organic material layer containing the compound is an organic electroluminescent device that is a phosphorescent light emitting layer.