KR20160078138A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic compound, and to an organic electroluminescent device comprising the same in at least one organic matter layer, thereby improving properties such as a light-emitting efficiency, a driving voltage, durability, etc.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound and an organic electroluminescent device including the organic compound.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer and holes are injected into the organic layer. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

As the hole injecting material, the hole transporting material, the hole blocking material, and the electron transporting material, NPB, BCP, and Alq ₃ have been known to date. Examples of the light emitting material include anthracene derivatives; Metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like; 4,4-dicarbazolybiphenyl (CBP) and the like are known.

However, these materials have low glass transition temperature and poor thermal stability, which is not satisfactory in terms of lifetime of an organic electroluminescent device.

It is an object of the present invention to provide a novel organic compound capable of enhancing hole injecting / transporting ability and light emitting ability of an organic electroluminescent device.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound.

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

[Chemical Formula 1]

In Formula 1,

X ₁ and X ₂ is selected from the group consisting of the same or different and are each independently selected from _{O, S, N (Ar 1} ), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ), wherein at least one of X ₁ and X ₂ is N (Ar _1),

Y ₁ to Y ₁₂ are the same or different and each independently N or C (R ₁ )

R ₁ to R ₃ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alk group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ alkyloxy A C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron An arylphosphine group having ₆ to ₆₀ carbon atoms, an arylphosphine group having ₆ to ₆₀ carbon atoms, an arylphosphine oxide group having ₆ to ₆₀ carbon atoms and an arylamine group having ₆ to ₆₀ carbon atoms, or is bonded to an adjacent group to form a condensed ring,

Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a nucleus 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, A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, A C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group,

The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group and arylsilyl group of R ₁ to R ₃ and Ar ₁ to Ar ₅ , An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group , A C ₃ to 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, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group , C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ unsubstituted arylamine And, wherein, if substituted with a plurality of substituents, the plurality of substituents are the same or different.

The present invention also provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound And an organic electroluminescent device.

In the present invention, "alkyl" means 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 and hexyl.

In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples of such alkynyls include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention 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. Two or more rings may be pendant or condensed with each other. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, two or more rings may include a pendant or condensed form with each other, and may further include a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

In the present invention, "alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and may be linear, branched or cyclic . ≪ / RTI > Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and " silyl " means silyl substituted with aryl having 5 to 40 carbon atoms.

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

The compound represented by the general formula (1) of the present invention is excellent in hole transporting property, thermal stability and light emitting property and can be used as a material of 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 in a light emitting layer, an organic electroluminescent device having excellent light emitting performance, driving voltage, efficiency, and lifetime characteristics can be manufactured. Further, Color display panels can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The compound of the present invention has a linear skeleton in which an aromatic ring group (specifically, phenyl group) is bonded to both sides of a heteroaromatic ring, and is represented by the above formula (1). The compound represented by formula (1) of the present invention has a high energy level because an aromatic ring group is bonded to both sides of a heteroaromatic ring in which an indole derivative having a broad singlet energy level and a high triplet energy level are condensed.

In addition, the compound represented by formula (1) of the present invention may have a wide band gap because the HOMO and LUMO energy levels are controlled depending on the type of substituent introduced into the basic skeleton. In addition, since various substituents are introduced into the basic skeleton, the molecular weight is significantly increased to have a high glass transition temperature, so that the thermal stability is excellent.

Accordingly, when the compound represented by Formula 1 of the present invention is applied to an organic material layer of an organic electroluminescent device, the driving voltage, current efficiency, light emission characteristic, and lifetime characteristics of the organic electroluminescent device can be greatly improved.

Specifically, when the compound represented by the formula (1) of the present invention is applied to the light emitting layer in the organic material layer, the coupling efficiency between the holes and electrons injected into the light emitting layer is improved, thereby improving the luminous efficiency of the organic electroluminescent device. In addition, when the compound represented by the general formula (1) of the present invention is applied to the luminescent auxiliary layer or the lifetime improving layer in the organic material layer, the excitons generated in the luminescent layer can be prevented from diffusing into the adjacent electron transporting layer or hole transporting layer, The luminous efficiency of the device can be increased. In addition, the compound represented by Formula 1 of the present invention has excellent carrier transportability and can be applied to a hole injection layer or a hole transport layer in the organic material layer.

The compound represented by formula (1) of the present invention is preferably any one of compounds represented by the following formulas (C-1) to (C-5).

In the above formulas C-1 to C-5,

R _2, R ₃ , Y ₁ to Y _12, and Ar ₁ to Ar ₅ are the same as defined in Formula 1 above.

In the compound represented by the general formula (1) of the present invention, X ₁ and X ₂ are preferably O, S or N (Ar ₁ ), and more preferably all of N (Ar ₁ ).

It is preferable that one of Y ₁ to Y ₁₂ is N or both C (R ₁ ). In this case, R ₁ may condense with adjacent R ₁ to form an aromatic ring or a heteroaromatic ring.

In addition, R ₁ to R ₃ is selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms aryl of from 5 to 60 heteroaryl group, and a C ₆ ~ with an aryl amine of the C ₆₀ of the .

Further, Ar ₁ to Ar ₅ is selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms aryl of from 5 to 60 heteroaryl group, and a C ₆ ~ with an aryl amine of the C ₆₀ of the .

Specifically, at least one of R ₁ to R ₃ and Ar ₁ to Ar ₅ (particularly, at least one of Ar ₁ to Ar ₅ ) is preferably a substituent represented by the following formula (2).

(2)

In Formula 2,

* Represents a moiety bonded to Formula 1,

L ₁ is selected from the group consisting of a heteroarylene of a single bond, a C ₆ ~ C ₁₈ arylene group and a nuclear atoms of 5 to 18 (preferably a single bond, phenylene group, biphenylene group, carbazole group),

Z ₁ to Z ₅ are the same or different and each independently N or C (R ₁₁ ), wherein when C (R ₁₁ ) is plural, they are the same or different,

R ₁₁ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, nuclear atoms heteroaryl of 5 to 60 group, C ₆ ~ aryloxy C ₄₀ C ₁ ~ C ₄₀ alkyloxy group, the C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, A C ₆ to C ₄₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, combined with a C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ group (e.g., L or adjacent to other R ₁₁ to) selected from the group consisting arylsilyl of C _40, or adjacent, to form a condensed ring.

Alkyl group of the R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of 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 alkoxy A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group, C ₆ ~ C ₄₀ aryl substituted with a phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ of Or is unsubstituted, wherein the case be substituted with plural substituents, the plural substituents are the same or different.

The substituent represented by the formula (2) may be embodied by any one of the substituents represented by the following A-1 to A-16, but is not limited thereto.

In the above A-1 to A-16,

L ₁ and R ₁₁ are the same as defined in Formula 2,

R ₁₂ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group , C ₆ to C ₄₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups , in combination with a C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ group (e. g., L _1, R ₁₁ or other R ₁₂₎ is selected from the group consisting arylsilyl of C _40, or adjacent a condensed ring Forming,

n is an integer of 0 to 4;

Alkyl group of the R _12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of 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 alkoxy A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group, C ₆ ~ C ₄₀ aryl substituted with a phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ of Or is unsubstituted, wherein the case be substituted with plural substituents, the plural substituents are the same or different.

At least one of R ₁ to R ₃ and Ar ₁ to Ar ₅ (particularly, at least one of Ar ₁ to Ar ₅ ) is preferably a substituent represented by the following general formula (3).

(3)

In Formula 3,

* Represents a moiety bonded to Formula 1,

L ₂ is selected from the group consisting of a heteroarylene of a single bond, a C ₆ ~ C ₁₈ arylene group and a nuclear atoms of 5 to 18 (preferably a single bond, phenylene group, biphenylene group, carbazole group),

R ₁₃ and R ₁₄ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine Group, or combine to form a condensed ring,

The alkyl, aryl, heteroaryl and arylamine groups of R ₁₃ and R ₁₄ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ substituted from the group consisting arylsilyl of C ₄₀ of at least one selected more substituents, or And when the substituent is substituted with a plurality of substituents, the plurality of substituents may be the same or different.

More specific examples of the compound represented by the formula (1) of the present invention include, but are not limited to, the following compounds (1 to 218).

2. Organic electroluminescent device

The present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).

Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, And a compound represented by the formula (1). At this time, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a hole blocking layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and an electron injecting layer. . ≪ / RTI > Specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer or a hole transporting layer. The light emitting layer may include a host, wherein the host may include a compound represented by Formula 1 or a compound other than the compound represented by Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially laminated. At this time, an electron injection layer may be further stacked on the electron transport layer. An insulating layer or an adhesive layer may be further inserted into the interface between the anode and the cathode and the organic layer.

The organic electroluminescent device of the present invention can be produced by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula .

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

The substrate used in the production of the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film, or the like can be used.

Examples of the positive electrode 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); A combination of a metal and an oxide 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 are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

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

 [Preparation Example 1] Synthesis of Sub 1-1

(53.18 g, 200.0 mmol), phenyl acetylene (40.86 g, 400.0 mmol), Cs ₂ CO ₃ (260.66 g, 800.0 mmol), and [Cu (phen) PPh ₃ ) ₂ ] NO ₃ (33.21 g, 40.0 mmol) and toluene (2 L) were mixed and stirred at 110 ° C. for 24 hours. Sodium butoxide (115.32 g, 1200.0 mmol) was added thereto, followed by stirring at 110 ° C for 2 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then dried over MgSO ₄ . After removing the solvent of the filtered organic layer Sub-1-1 (39.47 g, yield: 64%) was obtained by purification by column chromatography.

GC-Mass (theory: 308.38 g / mol, measurement: 308 g / mol)

^{1 H-NMR: δ 6.82 (} s, 2H), δ 7.52 (m, 6H), δ 7.64 (s, 2H), δ 7.90 (d, 4H), δ 11.29 (brs, 2H)

[Preparation Example 2] Synthesis of Sub 1-1-1

Bromobenzene (15.70 g, 100.0 mmol), Pd (OAc) ₂ (1.12 g, 5.0 mmol), K ₃ PO ₄ (63.68 g, 300.0 mmol) synthesized in Preparation Example 1 ), P (t-bu) ₃ (2.02 g, 10.0 mmol) and toluene (500 ml) were mixed and stirred at 110 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then dried over MgSO ₄ . After removing the solvent of the filtered organic layer Purification by column chromatography afforded Sub 1-1-1 (28.45 g, yield 74%).

GC-Mass (calculated: 384.48 g / mol, measured: 384 g / mol)

^{1 H-NMR: δ 6.81 (} d, 2H), δ 7.51 (m, 8H), δ 7.60 (m, 3H), δ 7.83 (m, 3H), δ 7.93 (m, 3H), δ 11.29 (brs, 1H)

[Preparation Example 3] Synthesis of Sub 2-1

The procedure of Preparation Example 1 was repeated except that 4-amino-2,5-dibromophenol (53.38 g, 200.0 mmol) was used instead of 2,5-dibromobenzene-1,4-diamine used in Preparation Example 1 Sub 2-1 (37.74 g, yield: 61%) was obtained.

GC-Mass (theory: 309.37 g / mol, measurement: 309 g / mol)

^{1 H-NMR: δ 6.82 (} s, 1H), δ 7.14 (s, 1H), δ 7.55 (m, 6H), δ 7.65 (s, 1H), δ 7.72 (s, 1H), δ 7.90 (d, 2H), 8 8.07 (d, 2H), 8 11.29 (brs, 1 H)

[Preparation Example 4] Synthesis of Sub 3-1

The procedure of Preparation Example 1 was repeated except that 4-amino-2,5-dibromobenzenethiol (56.60 g, 200.0 mmol) was used instead of 2,5-dibromobenzene-1,4-diamine used in Preparation Example 1 Sub 3-1 (41.00 g, yield: 63%) was obtained.

GC-Mass (calculated: 325.43 g / mol, measured: 325 g / mol)

^{1 H-NMR: δ 6.82 (} s, 1H), δ 7.55 (m, 7H), δ 7.82 (d, 2H), δ 7.90 (m, 3H), δ 7.99 (s, 1H), δ 11.29 (brs, 1H)

[Preparation Example 5] Synthesis of Sub 1-1-1-1

Except that Sub 1-1-1 (38.45 g, 100.0 mmol) was used instead of Sub 1-1 used in Preparation Example 2 and 1-bromo-4-iodobenzene (28.29 g, 100.0 mmol) was used instead of bromobenzene. Sub 1-1-1-1 (41.54 g, yield: 77%) was obtained by the same procedure as Preparation Example 2 above.

GC-Mass (calculated: 539.48 g / mol, measured: 539 g / mol)

^{1 H-NMR: δ 6.80 (} s, 2H), δ 7.51 (m, 8H), δ 7.60 (m, 5H), δ 7.68 (d, 2H), δ 7.83 (m, 5H), δ 7.96 (s, 1H)

[Preparation Example 6] Synthesis of Sub 1-2

Sub-1-2 (48.20 g, yield: 59%) was prepared following the same procedure as in Preparation Example 1, except that 2-ethynylnaphthalene (60.88 g, 400.0 mmol) was used instead of the phenyl acetylene used in Preparation Example 1 .

GC-Mass (theory: 408.50 g / mol, measurement: 408 g / mol)

^{1 H-NMR: δ 6.82 (} s, 2H), δ 7.62 (m, 6H), δ 8.02 (m, 8H), δ 8.46 (s, 2H), δ 11.29 (brs, 2H)

[Preparation Example 7] Synthesis of Sub 1-2-1

Sub-1-2 (40.85 g, 100.0 mmol) synthesized in Preparation Example 6 was used instead of Sub 1-1 used in Preparation Example 2, and Sub 1-2- 1 (36.83 g, yield: 76%).

GC-Mass (calculated: 484.60 g / mol, measured: 484 g / mol)

^{1 H-NMR: δ 6.81 (} d, 2H), δ 7.50 (d, 2H), δ 7.60 (m, 8H), δ 7.81 (s, 1H), δ 8.00 (m, 8H), δ 8.46 (s, 2H), 8 11.29 (brs, 1 H)

[Preparation Example 8] Synthesis of Sub 2-1-1

Sub-2-1 (30.94 g, 100.0 mmol) synthesized in Preparation Example 3 was used instead of Sub 1-1 used in Preparation Example 2, and 1-bromo-4-iodobenzene (28.29 g, 100.0 mmol) was used in place of bromobenzene , Sub 2-1-1 (34.83 g, yield: 75%) was obtained by carrying out the same procedure as Preparation Example 2 above.

GC-Mass (calculated: 464.36 g / mol, measured: 464 g / mol)

^{1 H-NMR: δ 6.80 (} s, 1H), δ 7.14 (s, 1H), δ 7.59 (m, 12H), δ 7.84 (d, 2H), δ 8.07 (d, 2H)

[Preparation Example 9] Synthesis of Sub 3-1-1

Sub-3-1 (32.54 g, 100.0 mmol) synthesized in Preparation Example 4 was used instead of Sub 1-1 used in Preparation Example 2, and 1-bromo-4-iodobenzene (28.29 g, 100.0 mmol) was used instead of bromobenzene , Sub 3-1-1 (35.55 g, yield: 74%) was obtained by carrying out the same procedure as Preparation Example 2 above.

GC-Mass (theory: 480.42 g / mol, measurement: 480 g / mol)

¹ H-NMR:? 6.80 (s, 1 H),? 7.58 (m, 11H),? 7.83 (m, 4H),? 7.91

[Preparation Example 10] Synthesis of Sub 1-1-2

Except that 4-bromo-1,1'-biphenyl (23.31 g, 100.0 mmol) was used instead of bromobenzene used in Preparation Example 2, Sub 1-1-2 (33.16 g, yield: 72%).

GC-Mass (theory: 460.58 g / mol, measured: 460 g / mol)

¹ H-NMR:? 6.81 (d, 2H),? 7.48 (m, 9H),? 7.86 (m, 12H)

[Preparation Example 11] Synthesis of Sub 1-1-3

Except that 3-bromo-1,1'-biphenyl (23.31 g, 100.0 mmol) was used instead of bromobenzene used in Preparation Example 2, Sub 1-1-3 (32.24 g, yield: 70%).

GC-Mass (theory: 460.58 g / mol, measured: 460 g / mol)

^{1 H-NMR: δ 6.81 (} d, 2H), δ 7.69 (m, 20H), δ 8.21 (s, 1H), δ 11.29 (brs, 1H)

[Preparation Example 12] Synthesis of Sub 1-1-4

Except that 5'-bromo-1,1 ': 3', 1 "-terphenyl (30.92 g, 100.0 mmol) was used instead of the bromobenzene used in Preparation Example 2, Sub 1-1-4 (38.1 g, yield: 71%).

GC-Mass (calculated: 536.68 g / mol, measured: 536 g / mol)

^{1 H-NMR: δ 6.81 (} d, 2H), δ 7.48 (m, 12H), δ 7.83 (m, 11H), δ 8.31 (s, 2H), δ 11.29 (brs, 1H)

[Synthesis Example 1] Synthesis of compound 1

(19.23 g, 50.0 mmol), 4-bromo-N, N-diphenylaniline (16.21 g, 50.0 mmol), Pd (OAc) ₂ (0.56 g, 2.5 mmol), K ₃ PO ₄ (31.84 g, 150.0 mmol), P (t-bu) ₃ (1.01 g, 5.0 mmol) and toluene (300 ml) were mixed and stirred at 110 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then dried over MgSO ₄ . After removing the solvent of the filtered organic layer Purification by column chromatography gave compound 1 (21.97 g, yield 70%).

GC-Mass (calculated: 627.79 g / mol, measured: 627 g / mol)

[Synthesis Example 2] Synthesis of compound 5

4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine in place of 4-bromo-N, N- diphenylaniline (23.82 g , 50.00 mmol), the same procedure as in Synthesis Example 1 was conducted to obtain compound 5 (28.86 g, yield: 74%).

GC-Mass (calculated: 779.99 g / mol, measured: 779 g / mol)

[Synthesis Example 3] Synthesis of compound 11

Except that 3-bromo-9-phenyl-9H-carbazole (16.11 g, 50.00 mmol) was used in place of 4-bromo-N, N-diphenylaniline 11 (19.09 g, yield: 61%).

GC-Mass (calculated: 625.78 g / mol, measured: 625 g / mol)

[Synthesis Example 4] Synthesis of compound 12

4-bromo-N, N- diphenylaniline place of ^{N 1 - ([1,1'-biphenyl} ] -4-yl) -N 1 - (4'-bromo- [1,1'-biphenyl] -4-yl) Compound 32 (32.2 g, yield: 68%) was prepared following the same procedure as in Synthesis Example 1, except that -N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine (32.18 g, 50.00 mmol) .

GC-Mass (947.2 g / mol, measured: 947 g / mol)

[Synthesis Example 5] Synthesis of compound 15

The procedure of Synthesis Example 1 was repeated except that Sub 1-1-1-1 (26.97 g, 50.00 mmol) synthesized in Preparation Example 5 was used instead of 4-bromo-N, N-diphenylaniline to obtain compound 15 (32.88 g, yield: 78%).

GC-Mass (calculated: 843.05 g / mol, measured: 843 g / mol)

[Synthesis Example 6] Synthesis of compound 18

Sub-2-1 (15.47 g, 50.00 mmol) synthesized in Preparation Example 3 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and 9- (4-bromophenyl ) -9H-carbazole (16.11 g, 50.00 mmol) was used in place of the compound 18 (16.52 g, yield: 60%).

GC-Mass (calculated: 550.67 g / mol, measured: 550 g / mol)

[Synthesis Example 7] Synthesis of compound 22

Sub-2-1 (15.47 g, 50.00 mmol) synthesized in Preparation Example 3 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and 9- (4-bromophenyl (27.06 g, yield: 77%) was obtained in the same manner as in Synthesis Example 1, except that 3,6-diphenyl-9H-carbazole (23.72 g, 50.00 mmol)

GC-Mass (calculated: 702.86 g / mol, measured: 702 g / mol)

[Synthesis Example 8] Synthesis of compound 26

Sub-2-1 (15.47 g, 50.00 mmol) synthesized in Preparation Example 3 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and 3-bromo-9- Compound 26 (20.37 g, yield: 74%) was obtained in the same manner as in Synthesis Example 1, except that phenyl-9H-carbazole (16.11 g, 50.00 mmol) was used.

GC-Mass (calculated: 550.67 g / mol, measured: 550 g / mol)

[Synthesis Example 9] Synthesis of compound 31

The procedure of Synthesis Example 1 was repeated except that Sub 3-1 (16.27 g, 50.00 mmol) synthesized in Preparation Example 4 was used instead of Sub 1-1-1 synthesized in Preparation Example 2 to obtain compound 31 17.63 g, yield: 62%).

GC-Mass (calculated: 568.74 g / mol, measured: 568 g / mol)

[Synthesis Example 10] Synthesis of compound 36

Instead of 4-bromo-N, N-diphenylaniline, Sub 3-1 (16.27 g, 50.00 mmol) synthesized in Preparation Example 4 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, Synthesis Example 1 was repeated except for using [1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4-amine (27.63 g, 50.00 mmol) The same procedure was followed to obtain compound 36 (29.89 g, yield: 75%).

GC-Mass (calculated: 797.04 g / mol, measured: 797 g / mol)

[Synthesis Example 11] Synthesis of compound 44

Sub 3-1 (16.27 g, 50.00 mmol) synthesized in Preparation Example 4 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and 3-1-1 (4-bromo-N, 24.02 g, 50.00 mmol), the same procedure as in Synthesis Example 1 was conducted to obtain compound 44 (25.01 g, yield 69%).

GC-Mass (calculated: 724.94 g / mol, measured: 724 g / mol)

[Synthesis Example 12] Synthesis of compound 46

Except that Sub 1-1-2 (23.03 g, 50.00 mmol) synthesized in Preparation Example 10 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and compound 46 (24.28 g, yield 69%).

GC-Mass (calculated: 703.89 g / mol, measured: 703 g / mol)

[Synthesis Example 13] Synthesis of compound 54

Sub - 1-1-2 (23.03 g, 50.00 mmol) synthesized in Preparation Example 10 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and N - ([ 4-yl) -N- (3-bromophenyl) - [1,1'-biphenyl] -4-amine (23.82 g, 50.00 mmol) 1, the compound 54 (29.96 g, yield: 70%) was obtained.

GC-Mass (calculated: 856.09 g / mol, measured: 856 g / mol)

[Synthesis Example 14] Synthesis of compound 57

Using a Sub 1-1-2 (23.03 g, 50.00 mmol ) synthesized in Preparation Example 10 instead of the Sub 1-1-1 synthesized in Preparation Example 2, 4-bromo-N, N -diphenylaniline place of N ¹ - ( [1,1'-biphenyl] -4-yl) -N ¹ - (4'-bromo- [1,1'-biphenyl] -4-yl) -N ⁴ , N ⁴ -diphenylbenzene- (35.82 g, yield: 70%) was obtained by carrying out the same processes as in Synthesis Example 1, except that the starting material (32.18 g, 50.00 mmol) was used.

GC-Mass (calculated: 1023.3 g / mol, measured: 1023 g / mol)

[Synthesis Example 15] Synthesis of compound 61

Except that Sub 1-1-3 (23.03 g, 50.00 mmol) synthesized in Preparation Example 11 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and compound 61 (22.52 g, yield: 64%).

GC-Mass (calculated: 703.89 g / mol, measured: 703 g / mol)

[Synthesis Example 16] Synthesis of compound 67

Sub 1-1-3 (23.03 g, 50.00 mmol) synthesized in Preparation Example 11 was used instead of 4-bromo-N, N-diphenylaniline and 9- (4 (27.76 g, yield: 65%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromophenyl) -3,6-diphenyl-9H-carbazole (23.72 g, 50.00 mmol) .

GC-Mass (calculated: 854.07 g / mol, measured: 854 g / mol)

[Synthesis Example 17] Synthesis of compound 71

Sub-1-1-3 (23.03 g, 50.00 mmol) synthesized in Preparation Example 11 was used instead of 4-bromo-N, N-diphenylaniline and 3-bromo- The compound 71 (23.16 g, yield: 66%) was obtained in the same manner as in Synthesis Example 1, except that 9-phenyl-9H-carbazole (16.11 g, 50.00 mmol) was used.

GC-Mass (701.88 g / mol, measured: 701 g / mol)

[Synthesis Example 18] Synthesis of compound 73

Instead of Sub 1-1-1 synthesized in Preparation Example 2, Sub 1-1-3 (23.03 g, 50.00 mmol) synthesized in Preparation Example 11 was used instead of 4-bromo-N, N- diphenylaniline, 1 (23.22 g, 50.00 mmol), the compound 73 (27.85 g, yield: 66%) was obtained in the same manner as in Synthesis Example 1.

GC-Mass (calculated: 844.03 g / mol, measured: 844 g / mol)

[Synthesis Example 19] Synthesis of compound 76

Except that Sub 1-2-1 (24.23 g, 50.00 mmol) synthesized in Preparation Example 7 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and compound 76 (22.57 g, yield: 62%).

GC-Mass (calculated: 727.91 g / mol, measured: 727 g / mol)

[Synthesis Example 20] Synthesis of compound 92

Sub-1-1-4 (26.83 g, 50.00 mmol) synthesized in Preparation Example 12 was used instead of 4-bromo-N, N-diphenylaniline and 3-bromo- Compound 92 (24.96 g, yield: 64%) was obtained in the same manner as in Synthesis Example 1, except that N, N-diphenylaniline (16.21 g, 50.00 mmol) was used.

GC-Mass (calculated: 779.99 g / mol, measured: 779 g / mol)

[Synthesis Example 21] Synthesis of compound 106

Except that 2- (3-bromophenyl) triphenylene (19.16 g, 50.00 mmol) was used in place of 4-bromo-N, N-diphenylaniline to obtain compound 106 (23.01 g, yield: 67%).

GC-Mass (calculated: 686.86 g / mol, measured: 686 g / mol)

[Synthesis Example 22] Synthesis of compound 108

Except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (19.41 g, 50.00 mmol) was used in place of 4-bromo-N, N-diphenylaniline. The same procedure was followed to obtain compound 108 (21.45 g, yield: 62%).

GC-Mass (calculated: 691.84 g / mol, measured: 691 g / mol)

[Synthesis Example 23] Synthesis of compound 112

.

.

The same procedure as in Synthesis Example 1 was repeated except that 2- (4-bromophenyl) -4,6-diphenylpyrimidine (19.36 g, 50.00 mmol) was used instead of 4-bromo-N, N-diphenylaniline. 26.6 g, yield: 77%).

GC-Mass (calculated: 690.85 g / mol, measured: 690 g / mol)

[Synthesis Example 24] Synthesis of compound 113

The procedure of Synthesis Example 1 was repeated except that 2-bromo-9,9-dimethyl-9H-fluorene (13.66 g, 50.00 mmol) was used instead of 4-bromo-N, N-diphenylaniline. 17.88 g, yield: 62%).

GC-Mass (calculated: 576.74 g / mol, measured: 576 g / mol)

[Synthesis Example 25] Synthesis of compound 115

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline (18.06 g, 50.00 mmol) was used in place of 4-bromo-N, N-diphenylaniline Was performed to obtain compound 115 (26.59 g, yield: 80%).

GC-Mass (calculated: 664.81 g / mol, measured: 664 g / mol)

[Synthesis Example 26] Synthesis of compound 117

.

.

Instead of Sub 1-1-1 synthesized in Preparation Example 2, Sub 1-1 (15.42 g, 50.00 mmol) synthesized in Preparation Example 1 was used instead of 4-bromo-N, N- diphenylaniline and bromobenzene (15.7 g, 100.00 mmol), the same procedure as in Synthesis Example 1 was conducted to obtain compound 117 (14.97 g, yield 65%).

GC-Mass (theory: 460.58 g / mol, measured: 460 g / mol)

[Synthesis Example 27] Synthesis of compound 124

Sub 2-1 (15.47 g, 50.00 mmol) synthesized in Preparation Example 3 was used instead of Sub 1-1-1 synthesized in Preparation Example 2 and 2-bromotriphenylene (15.36 g, 50.00 mmol) was used instead of 4-bromo-N, N-diphenylaniline , 50.00 mmol), the same procedure as in Synthesis Example 1 was conducted to obtain compound 124 (16.87 g, yield: 63%).

GC-Mass (calculated: 535.65 g / mol, measured: 535 g / mol)

[Synthesis Example 28] Synthesis of compound 126

Sub 2-1 (15.47 g, 50.00 mmol) synthesized in Preparation Example 3 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and 2- (3-bromophenyl (19.12 g, yield: 62%) was obtained in the same manner as in Synthesis Example 1, except that 4,6-diphenyl-1,3,5-triazine (19.41 g, ≪ / RTI >

GC-Mass (calculated: 616.73 g / mol, measured: 616 g / mol)

[Synthesis Example 29] Synthesis of compound 131

Sub-2-1 (15.47 g, 50.00 mmol) synthesized in Preparation Example 3 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and 2-bromo-4- The compound 131 (17.72 g, yield: 69%) was obtained in the same manner as in Synthesis Example 1, except that phenylquinazoline (14.26 g, 50.00 mmol) was used.

GC-Mass (calculated: 513.6 g / mol, measured: 513 g / mol)

[Synthesis Example 30] Synthesis of compound 144

Instead of 4-bromo-N, N-diphenylaniline, Sub 3-1 (16.27 g, 50.00 mmol) synthesized in Preparation Example 4 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, The same procedure as in Synthesis Example 1 was carried out except that bromo- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine (23.22 g, 50.00 mmol) To give compound 144 (28 g, yield: 79%).

GC-Mass (708.89 g / mol, measured: 708 g / mol)

[Synthesis Example 31] Synthesis of compound 150

Instead of 4-bromo-N, N-diphenylaniline, Sub 3-1 (16.27 g, 50.00 mmol) synthesized in Preparation Example 4 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, (22.63 g, yield: 69%) was obtained by following the same procedure as in Synthesis Example 1, except that 4- (naphthalen-1-yl) phenylquinazoline (20.57 g, 50.00 mmol) .

GC-Mass (calculated: 655.82 g / mol, measured: 655 g / mol)

[Synthesis Example 32] Synthesis of compound 164

Instead of 4-bromo-N, N-diphenylaniline, Sub 1-1-2 (23.03 g, 50.00 mmol) synthesized in Preparation Example 10 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, Compound 164 (23.5 g, yield: 72%) was obtained in the same manner as in Synthesis Example 1, except that 9,9-dimethyl-9H-fluorene (13.66 g, 50.00 mmol) was used.

GC-Mass (calculated: 652.84 g / mol, measured: 652 g / mol)

[Synthesis Example 33] Synthesis of compound 168

Sub-1-1 (15.42 g, 50.00 mmol) synthesized in Preparation Example 1 was used instead of 4-bromo-N, (21.45 g, yield: 70%) of compound 168 was obtained in the same manner as in Synthesis Example 1, except that 1'-biphenyl (23.31 g, 100.00 mmol) was used.

GC-Mass (calculated: 612.78 g / mol, measured: 612 g / mol)

[Synthesis Example 34] Synthesis of compound 169

Sub-1-1-2 (23.03 g, 50.00 mmol) synthesized in Preparation Example 10 was used instead of 4-bromo-N, N-diphenylaniline and 3-bromo- The compound 169 (19.92 g, yield: 65%) was obtained in the same manner as in Synthesis Example 1, except that 1,1'-biphenyl (11.66 g, 50.00 mmol) was used.

GC-Mass (calculated: 612.78 g / mol, measured: 612 g / mol)

[Synthesis Example 35] Synthesis of compound 171

Sub-1-1-2 (23.03 g, 50.00 mmol) synthesized in Preparation Example 10 was used instead of 4-bromo-N, N-diphenylaniline and 4-bromo- Compound 171 (26.87 g, yield: 78%) was obtained in the same manner as in Synthesis Example 1, except that 1,1 ': 4', 1 "-terphenyl (15.46 g, 50.00 mmol) .

GC-Mass (calculated: 688.88 g / mol, measured: 688 g / mol)

[Synthesis Example 36] Synthesis of compound 173

Instead of 4-bromo-N, N-diphenylaniline, Sub 1-1-3 (23.03 g, 50.00 mmol) synthesized in Preparation Example 11 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, -bromophenyl) triphenylene (19.16 g, 50.00 mmol) was used in place of the compound 173 (29.37 g, yield: 77%).

GC-Mass (calculated: 762.96 g / mol, measured: 762 g / mol)

[Synthesis Example 37] Synthesis of compound 181

Sub-1-1-3 (23.03 g, 50.00 mmol) synthesized in Preparation Example 11 was used instead of 4-bromo-N, N-diphenylaniline and 2-bromo- Compound 181 (26.26 g, yield: 79%) was obtained by following the procedure of Synthesis Example 1, except that 4-phenylquinazoline (14.26 g, 50.00 mmol) was used.

GC-Mass (calculated: 664.81 g / mol, measured: 664 g / mol)

[Synthesis Example 38] Synthesis of compound 199

Sub-1-2 (20.43 g, 50.00 mmol) synthesized in Preparation Example 6 was used instead of Sub 1-1-1 synthesized in Preparation Example 2 and bromobenzene (15.7 g, 100.00 mmol) was used instead of 4-bromo-N, N-diphenylaniline mmol), the same procedure as in Synthesis Example 1 was carried out to obtain compound 199 (21.03 g, yield: 75%).

GC-Mass (calculated: 560.7 g / mol, measured: 560 g / mol)

[Synthesis Example 39] Synthesis of compound 206

Sub 1-1-4 (26.83 g, 50.00 mmol) synthesized in Preparation Example 12 was used instead of Sub 1-1-1 synthesized in Preparation Example 2, and 2-bromotriphenylene ( 15.36 g, 50.00 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain compound 206 (24.8 g, yield 65%).

GC-Mass (calculated: 762.96 g / mol, measured: 762 g / mol)

[Synthesis Example 40] Synthesis of compound 207

Instead of 4-bromo-N, N-diphenylaniline was used instead of Sub 1-1-1-4 (26.83 g, 50.00 mmol) synthesized in Preparation Example 12 instead of Sub 1-1-1 synthesized in Preparation Example 2, (30.81 g, yield: 73%) was obtained by following the same procedure as in Synthesis Example 1, except that 4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (19.41 g, %).

GC-Mass (calculated: 844.04 g / mol, measured: 844 g / mol)

[Synthesis Example 41] Synthesis of compound 212

Sub-1-1-4 (26.83 g, 50.00 mmol) synthesized in Preparation Example 12 was used instead of 4-bromo-N, N-diphenylaniline and 2-bromo- Compound 212 (24.78 g, yield: 68%) was obtained in the same manner as in Synthesis Example 1, except that 9,9-dimethyl-9H-fluorene (13.66 g, 50.00 mmol) was used.

GC-Mass (calculated: 728.94 g / mol, measured: 728 g / mol)

[Synthesis Example 42] Synthesis of compound 215

Sub-1-1-4 (26.83 g, 50.00 mmol) synthesized in Preparation Example 12 was used instead of 4-bromo-N, N-diphenylaniline and 2-bromo- Compound 215 (33.38 g, yield: 77%) was obtained in the same manner as in Synthesis Example 1, except that 4- (4- (naphthalen-1-yl) phenyl) quinazoline (20.57 g, .

GC-Mass (calculated: 867.07 g / mol, measured: 867 g / mol)

[Synthesis Example 43] Synthesis of compound 216

Sub-1-1 (15.42 g, 50.00 mmol) synthesized in Preparation Example 1 was used instead of Sub-1-1-1 synthesized in Preparation Example 2, and 5'-bromo-1 Compound 216 (22.95 g, yield: 60%) was obtained in the same manner as in Synthesis Example 1, except that 1 ': 3', 1 "-terphenyl (30.92 g, 100.00 mmol) was used.

GC-Mass (calculated: 764.98 g / mol, measured: 764 g / mol)

 [Examples 1 to 20]

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then an organic electroluminescent device was prepared as follows.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech) The substrate was transferred to an evaporator.

(80 nm) / DS-H522 (Doosan Electronics Co., Ltd.) + 5% DS-501 (manufactured by Mitsubishi Chemical Corporation) synthesized in Synthesis Examples 1 to 20 on m-MTDATA (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

 [Comparative Example 1]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that NPB was used instead of the compound synthesized in Synthesis Example 1 as a hole transport material in the formation of the hole transport layer.

The structures of m-MTDATA, BCP and NPB used in Examples 1 to 20 and Comparative Example 1 are as follows.

[Experimental Example 1]

The organic electroluminescent devices manufactured in Examples 1 to 20 and Comparative Example 1 were measured for driving voltage and current efficiency at a current density of 10 mA / cm 2, and the results are shown in Table 1 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 1 One 4.71 20.2 Example 2 5 4.48 18.4 Example 3 11 4.38 18.6 Example 4 12 5.05 20.3 Example 5 15 4.30 20.7 Example 6 18 4.89 21.0 Example 7 22 4.88 21.1 Example 8 26 4.47 20.3 Example 9 31 4.71 19.1 Example 10 36 5.16 21.4 Example 11 44 4.50 18.5 Example 12 46 4.90 19.5 Example 13 54 4.85 18.4 Example 14 57 4.67 20.6 Example 15 61 4.24 21.3 Example 16 67 4.31 19.0 Example 17 71 4.27 18.7 Example 18 73 4.81 21.3 Example 19 76 4.27 19.0 Example 20 92 4.54 20.4 Comparative Example 1 NPB 5.20 18.1

As shown in Table 1, it can be confirmed that the case where the compound of the present invention is applied to the hole transporting layer (Examples 1 to 20) has higher current efficiency and driving voltage than the case where the conventional NPB is applied (Comparative Example 1).

 [Examples 21 to 40]

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was produced as follows.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech) The substrate was transferred to an evaporator.

(60 nm) / TCTA (80 nm) / each compound (40 nm) / CBP + 10% Ir (ppy) ₃ synthesized in Synthesis Examples 21 to 40 (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce a green organic electroluminescent device.

[Comparative Example 2]

A green organic electroluminescent device was fabricated in the same manner as in Example 21, except that the compound synthesized in Synthesis Example 1 was not used as the hole transporting material in the formation of the hole transporting layer.

The structures of m-MTDATA and BCP used in Examples 21 to 40 and Comparative Example 2 are as described above, and the structures of TCTA, CBP and Ir (ppy) ₃ are as follows.

[Experimental Example 2]

The green organic electroluminescent devices manufactured in Examples 21 to 40 and Comparative Example 2 were measured for driving voltage and current efficiency at a current density of 10 mA / cm 2, and the results are shown in Table 2 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 21 One 6.82 40.4 Example 22 5 6.70 44.6 Example 23 11 6.91 40.6 Example 24 12 6.87 42.6 Example 25 15 6.77 41.0 Example 26 18 6.88 40.1 Example 27 22 6.87 43.3 Example 28 26 6.70 41.8 Example 29 31 6.79 40.0 Example 30 36 6.71 44.3 Example 31 44 6.84 38.8 Example 32 46 6.80 38.6 Example 33 54 6.81 43.1 Example 34 57 6.78 40.5 Example 35 61 6.92 41.2 Example 36 67 6.71 40.2 Example 37 71 6.76 41.9 Example 38 73 6.72 39.6 Example 39 76 6.77 42.9 Example 10 92 6.82 40.5 Comparative Example 2 - 6.93 38.2

As shown in Table 2, it can be confirmed that the case where the compound of the present invention is applied to the hole transport layer (Examples 21 to 40) is more excellent in current efficiency and driving voltage than the case where only the conventional TCTA is applied (Comparative Example 2).

 [Examples 41 to 60]

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was prepared as follows.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech) The substrate was transferred to an evaporator.

(60 nm) / TCTA (80 nm) / each compound (40 nm) / CBP + 10% (piq) ₂ Ir (80 nm) synthesized in Synthesis Examples 41 to 60 was formed on the ITO transparent substrate (acac) (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to manufacture a red organic electroluminescent device.

[Comparative Example 3]

A red organic electroluminescent device was manufactured in the same manner as in Example 41 except that the compound synthesized in Synthesis Example 1 was not used as the hole transporting material in the formation of the hole transporting layer.

The structures of m-MTDATA, TCTA, CBP and BCP used in Examples 41 to 60 and Comparative Example 3 are as described above, and the structure of (piq) ₂ Ir (acac) used is as follows.

[Experimental Example 3]

The red organic electroluminescent devices manufactured in Examples 41 to 60 and Comparative Example 3 were measured for driving voltage and current efficiency at a current density of 10 mA / cm 2, and the results are shown in Table 3 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 41 One 5.00 10.0 Example 42 5 4.93 12.3 Example 43 11 5.08 12.0 Example 44 12 5.04 9.6 Example 45 15 4.98 11.3 Example 46 18 4.92 11.6 Example 47 22 5.13 9.1 Example 48 26 5.03 9.7 Example 49 31 5.14 8.7 Example 50 36 5.09 11.4 Example 51 44 4.99 9.3 Example 52 46 5.12 12.7 Example 53 54 5.02 10.0 Example 54 57 4.99 8.7 Example 55 61 4.95 10.7 Example 56 67 5.11 11.4 Example 57 71 4.99 12.3 Example 58 73 4.97 9.7 Example 59 76 5.18 11.1 Example 60 92 5.09 12.2 Comparative Example 3 - 5.25 8.2

As shown in Table 3, it can be confirmed that the case where the compound of the present invention is applied to the hole transport layer (Examples 41 to 60) is more excellent in current efficiency and driving voltage than the case where only the conventional TCTA is applied (Comparative Example 3).

 [Examples 61 to 80]

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was produced as follows.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred to an evaporator.

(15 nm) / ADN + 5% DS (15 nm) synthesized in Synthesis Examples 61 to 80 on the ITO transparent substrate (electrode) prepared as described above -305 (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce a blue organic electroluminescent device.

 [Comparative Example 4] Production of blue organic electroluminescent device

A blue organic electroluminescent device was fabricated in the same manner as in Example 61, except that the compound synthesized in Synthesis Example 1 was not used as the hole transporting material in the formation of the hole transporting layer.

The structures of NPB and BCP used in Examples 61 to 80 and Comparative Example 4 are as described above, and the structure of ADN used is as follows.

[Experimental Example 4]

The driving voltage and current efficiency of the blue organic electroluminescent device manufactured in each of Examples 61 to 80 and Comparative Example 4 were measured at a current density of 10 mA / cm 2, and the results are shown in Table 4 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 61 One 5.22 5.4 Example 62 5 5.30 6.5 Example 63 11 5.38 5.3 Example 64 12 5.31 6.9 Example 65 15 5.30 7.0 Example 66 18 5.55 5.9 Example 67 22 5.21 6.8 Example 68 26 5.14 5.8 Example 69 31 5.53 7.7 Example 70 36 5.59 7.3 Example 71 44 5.37 6.9 Example 72 46 5.49 6.5 Example 73 54 5.21 5.5 Example 74 57 5.46 6.5 Example 75 61 5.47 5.7 Example 76 67 5.19 7.0 Example 77 71 5.44 6.7 Example 78 73 5.18 7.5 Example 79 76 5.24 7.4 Example 80 92 5.31 4.9 Comparative Example 4 - 5.60 4.8

As shown in Table 4, it can be confirmed that the case where the compound of the present invention is applied to the hole transporting layer (Examples 61 to 80) is more excellent in the current efficiency and the driving voltage than the case where only the conventional NPB is applied (Comparative Example 4).

 [Examples 81 to 98]

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was produced as follows.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech) The substrate was transferred to an evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / synthesized in Synthesis Examples 21 to 24, 26 to 28, 30, 32 to 36, 38 to 41 and 43 on an ITO transparent substrate of compound _{+ 10% Ir (ppy) 3} (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) prepared by sequentially stacked with the green organic light emitting element Respectively.

[Comparative Example 5]

A green organic electroluminescent device was fabricated in the same manner as in Example 81 except that CBP was used instead of the compound synthesized in Synthesis Example 21 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , BCP and CBP used in Examples 81 to 98 and Comparative Example 5 are as described above.

[Experimental Example 5]

The green organic electroluminescent devices manufactured in Examples 81 to 98 and Comparative Example 5 were measured for driving voltage and current efficiency at a current density of 10 mA / cm 2, and the results are shown in Table 5 below.

Sample The light- The driving voltage (V) Current efficiency (cd / A) Example 81 106 6.80 40.4 Example 82 108 6.73 43.7 Example 83 112 6.78 41.6 Example 84 113 6.77 41.4 Example 85 117 6.54 41.5 Example 86 124 6.72 43.1 Example 87 126 6.64 40.5 Example 88 144 6.81 42.3 Example 89 164 6.82 39.4 Example 90 168 6.77 43.3 Example 91 169 6.74 43.1 Example 92 171 6.69 42.5 Example 93 173 6.79 41.1 Example 94 199 6.69 41.9 Example 95 206 6.60 41.3 Example 96 207 6.71 43.6 Example 97 212 6.56 42.2 Example 98 216 6.79 39.5 Comparative Example 5 CBP 6.93 38.2

As shown in Table 5, it can be confirmed that the current efficiency and the driving voltage are superior to those in the case where the compound of the present invention is applied to the light emitting layer (Examples 81 to 98) in the case of the conventional CBP and Comparative Example 5 (Comparative Example 5).

[Examples 99 to 103]

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was produced as follows.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

Each compound synthesized in m-MTDATA (60 nm) / TCTA (80 nm) / Synthesis Examples 25, 29, 31, 37 and 42 + 10% (piq) ₂ Ir (acac) nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in order to laminate was prepared in the red organic light emitting device.

[Comparative Example 6] Production of red organic electroluminescent device

A red organic electroluminescent device was fabricated in the same manner as in Example 99 except that CBP was used instead of the compound synthesized in Synthesis Example 21 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, (piq) ₂ Ir (acac), BCP and CBP used in Examples 99 to 103 and Comparative Example 6 are as described above.

[Experimental Example 6]

The driving voltage and the current efficiency were measured at a current density of 10 mA / cm 2 for the red organic electroluminescent devices manufactured in Examples 99 to 103 and Comparative Example 6, respectively, and the results are shown in Table 6 below.

Sample The light- The driving voltage (V) Current efficiency (cd / A) Example 99 115 6.90 40.4 Example 100 131 6.73 43.7 Example 101 150 6.78 41.6 Example 102 181 6.77 41.4 Example 103 215 6.54 41.5 Comparative Example 6 CBP 7.1 37.0

As shown in Table 6, it can be confirmed that the case where the compound of the present invention is applied to the organic material layer (Examples 99 to 103) is more excellent in the current efficiency and the driving voltage than the case where the conventional CBP is applied (Comparative Example 6).

Claims (9)

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

In Formula 1,
X ₁ and X ₂ is selected from the group consisting of the same or different and are each independently selected from _{O, S, N (Ar 1} ), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ), wherein at least one of X ₁ and X ₂ is N (Ar _1),
Y ₁ to Y ₁₂ are the same or different and each independently N or C (R ₁ )
R ₁ to R ₃ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alk group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ alkyloxy A C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron An arylphosphine group having ₆ to ₆₀ carbon atoms, an arylphosphine group having ₆ to ₆₀ carbon atoms, an arylphosphine oxide group having ₆ to ₆₀ carbon atoms and an arylamine group having ₆ to ₆₀ carbon atoms, or is bonded to an adjacent group to form a condensed ring,
Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a nucleus 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, A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, A C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group,
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group and arylsilyl group of R ₁ to R ₃ and Ar ₁ to Ar ₅ , An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group , A C ₃ to 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, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group , C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ unsubstituted arylamine And, wherein, if substituted with a plurality of substituents, the plurality of substituents are the same or different. The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of compounds represented by the following formulas C-1 to C-5:

In the above formulas C-1 to C-5,
R _2, R ₃ , Y ₁ to Y _12, and Ar ₁ to Ar ₅ are the same as defined in claim 1, respectively. The method according to claim 1,
At least one of R ₁ to R ₃ and Ar ₁ to Ar ₅ is a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ Arylamine group. ≪ / RTI > The method according to claim 1,
Wherein at least one of R ₁ to R ₃ and Ar ₁ to Ar ₅ is a substituent represented by the following general formula (2).
(2)

In Formula 2,
* Represents a moiety bonded to Formula 1,
L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Z ₁ to Z ₅ are the same or different and each independently N or C (R ₁₁ ), wherein when C (R ₁₁ ) is plural, they are the same or different,
R ₁₁ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, nuclear atoms heteroaryl of 5 to 60 group, C ₆ ~ aryloxy C ₄₀ C ₁ ~ C ₄₀ alkyloxy group, the C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, A C ₆ to C ₄₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl groups or as in the combined group adjacent to form a condensed ring,
Alkyl group of the R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of 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 alkoxy A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group, C ₆ ~ C ₄₀ aryl substituted with a phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ of Or is unsubstituted, wherein the case be substituted with plural substituents, the plural substituents are the same or different. 5. The method of claim 4,
Wherein the substituent represented by the formula (2) is selected from the group consisting of substituents represented by the following formulas (A-1) to (A-16).

In the above Formulas A-1 to A-16,
L ₁ and R ₁₁ are the same as defined in claim 4,
R ₁₂ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group , C ₆ to C ₄₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups , C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl groups or as in the combined group adjacent to form a condensed ring,
n is an integer from 0 to 4,
Alkyl group of the R _12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of 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 alkoxy A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group, C ₆ ~ C ₄₀ aryl substituted with a phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ of Or is unsubstituted, wherein the case be substituted with plural substituents, the plural substituents are the same or different. The method according to claim 1,
At least one of R ₁ to R ₃ and Ar ₁ to Ar ₅ is a substituent represented by the following general formula (3).
(3)

In Formula 3,
* Represents a moiety bonded to Formula 1,
L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
R ₁₃ and R ₁₄ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine Group, or combine to form a condensed ring,
The alkyl, aryl, heteroaryl and arylamine groups of R ₁₃ and R ₁₄ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ substituted from the group consisting arylsilyl of C ₄₀ of at least one selected more substituents, or And when the substituent is substituted with a plurality of substituents, the plurality of substituents may be the same or different. 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 6. 8. The method of claim 7,
The organic compound layer containing the compound is a light emitting layer,
Wherein the compound is a phosphorescent host of the light emitting layer. 8. The method of claim 7,
Wherein the organic compound layer containing the compound is a hole transport layer.