KR20170114814A - Organic 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 including the organic electroluminescent device, wherein the compound according to the present invention is used for an organic compound layer of an organic electroluminescent device, preferably a light emitting layer, Life and the like can be improved.

Description

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

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More specifically, the present invention relates to a novel organic compound having excellent hole transporting ability, electron transporting ability, and light emitting ability, , A driving voltage, a lifetime, and the like.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode, and electrons are injected from the cathode 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 contained in the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, or the like depending on its function.

The luminescent material may be classified into blue, green, and red luminescent materials according to luminescent colors, and yellow and orange luminescent materials necessary to realize better natural colors. Further, a host / dopant system can be used as a luminescent material in order to increase the luminous efficiency through increase of color purity and energy transfer.

The dopant material can 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. Since the phosphorescent dopant can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent dopant, studies on the phosphorescent dopant as well as the phosphorescent host have been conducted.

Currently, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. As the phosphorescent dopant material used for the light emitting layer, there is known a metal complex compound containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ , dicarbazolybiphenyl (CBP) is known.

However, conventional materials have low glass transition temperature and poor thermal stability, and thus are not satisfactory in terms of lifetime in an organic electroluminescent device, and still need improvement in terms of luminescent properties.

Korean Patent Laid-Open Publication No. 2013-0049275

It is an object of the present invention to provide a novel organic compound which is excellent in light emitting ability, hole transporting ability, hole injecting ability and the like and can be used as an organic material layer material.

Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which has low driving voltage, high luminous efficiency, and improved lifetime.

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

In Formula 1,

A is a five-membered ring containing or not containing at least one atom of N, O, S,

B is a 6-membered aromatic ring,

Ar ₁ is selected from the group consisting of hydrogen, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms,

L ₁ and and L ₂ are the same or different, each independently is a single bond, or is selected from the group consisting of a hetero arylene C ₆ ~ C ₆₀ arylene group and a nuclear atoms of 5 to 60, wherein L ₁ is X ₁ , X ₂ , and Y ₁ to Y ₄ ,

X ₁ is NR ₁ or CR ₂ R ₃ ,

X ₂ to X ₄ are the same or different and are each independently a single bond or are selected from the group consisting of S, O, NR ₄ and CR ₅ R ₆ , wherein at least one of X ₂ and X ₄ is a single bond And X ₃ and X ₄ are both a single bond,

Y ₁ to Y ₈ and Y ₁₁ to Y ₁₈ are each independently CR _7, wherein the plurality of R ₇ are the same as or different from each other,

R ₁ to R ₇ are the same or different from each other and each independently selected from the group consisting of hydrogen, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms, , R ₅ is combined with the other R ₅₎ to form a condensed aromatic ring or a fused heteroaromatic ring,

And won five rings of said A, and 6-membered aromatic ring of B, the aryl group of said Ar _1, a heteroaryl group, an arylene group of said L ₁ and L _2, heteroarylene group, aryl group of the R ₁ to R ₇ group, a heteroaryl group, each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C of ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ cycloalkyl in the group, a number of nuclear atoms of 3 to 40 aryl , 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 ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ An arylamine group, and the like. When the substituent is plural, they may be the same as or different from each other.

Also, the present invention is an organic electroluminescent device comprising a cathode, 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 material layers is a compound represented by the above formula And an organic electroluminescent device.

Since the compound of the present invention is excellent in heat resistance, hole injecting ability, hole transporting ability, and light emitting ability, it can be used as an organic material layer of an organic electroluminescent device, preferably as a hole injecting layer material, a hole transporting layer material, or a light emitting layer material.

In addition, the organic electroluminescent device including the compound of the present invention in the hole injection layer, the hole transporting layer, and / or the light emitting layer can greatly improve aspects of light emitting performance, driving voltage, lifetime, efficiency, A full color display panel, and the like.

Hereinafter, the present invention will be described in detail.

1. Organic compounds

Organic compounds of the invention are based, quinazoline and 5-membered ring (A) is bonded moiety "in the" two substituents, connected directly or linked via a linker group (L _2), is connected directly or linker (L ₁₎ As a basic skeleton, and is represented by the general formula (1). Wherein the substituent is selected from the group consisting of a carbazole moiety, a dimethylfluorene moiety, a dibenzothiophene moiety, a dibenzofuran moiety, a dimethylacridine moiety, a thianthrene moiety, a thianthrene moiety, a dibenzodioxin moiety, spirofluorene, and the like.

More specifically, the compound represented by the general formula (1) of the present invention is a compound in which a quinoline ring (A) such as cyclopentane, furan, pyrazole, imidazole, oxazole, thiophene or the like is bonded to quinazoline, Since it has a similar energy level, it can be adjusted to a higher level than the energy level of the dopant and can be applied as a host material and has higher triplet energies than quinazoline-bonded structures. Can be expected. In particular, a compound having a thiophene attached to a quinazoline may exhibit a longer wavelength than a compound having a quinazoline bonded to another 5-membered ring. In addition, when an aryl group (for example, phenyl or biphenyl) is introduced into the 5-membered ring (A), thermal stability is improved by blocking the reaction site.

The compound of Formula 1 has a higher molecular weight and a higher glass transition temperature than that of a compound having one substituent bonded to a moiety having a quinazoline and a 5-membered ring, and thus has excellent thermal stability. In addition, since the compound of formula (1) has a narrow band gap, HOMO energy level and LUMO energy level suitable for a host material of an organic material layer are excellent, and carrier transporting property and light emitting property are also excellent. At this time, in the compound of Formula 1, when the carbazole moiety forms a condensed aromatic ring (benzocarbazole), it may have a narrower bandgap. In the organic electroluminescent device including such a compound, Can be improved.

Furthermore, when the electron donating group (EWG) having a high electron absorbing property such as a nitrogen-containing heterocycle (for example, a pyridine group, a pyrimidine group, or a triazine group) is bonded to the basic skeleton, Since the whole molecule has a bipolar characteristic, it is possible to increase the bonding force between holes and electrons, and exhibit excellent carrier transporting property and light emitting property. Such a compound can be used not only as a light emitting layer material for an organic electroluminescence device but also as an electron injecting layer / transporting layer material and a life improving layer material.

In addition, when a large electron donor (EDG) such as an arylamine group, a carbazole group, a terphenyl group, and a triphenylene group is bonded to the basic skeleton of the compound of Formula 1, injection and transport of holes are smooth It can be used not only as a light emitting layer material but also as a hole injecting / transporting layer or a light emitting auxiliary layer material. In particular, a compound having a large electron donor group has high triplet energy, and therefore, when used as a hole transporting material, the efficiency can be expected to increase due to the triplet-triplet fusion (TTF) effect.

Therefore, the compound represented by the general formula (1) of the present invention can be used as an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (red phosphorescent host material), an electron transporting / injecting layer material and a hole transporting / Material, life-improving layer material, more preferably a light-emitting layer material, an electron-injecting layer material, and a hole-transporting layer material. In addition, the organic electroluminescent device including the compound of Formula 1 can be greatly improved in performance and lifetime, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize its performance.

The compound represented by formula (1) of the present invention may be represented by any one of the following formulas (2) to (5).

In the above formulas 2 to 5,

A, B, Ar _{1 ,} L ₂ , X ₁ to X ₄ , Y ₁ to Y ₈ , and Y ₁₁ to Y ₁₈ are as defined in Formula 1 above.

More specifically, the compound represented by the formula (1) may be a compound represented by any one of the following formulas (6) to (8).

In the above formulas (6) to (8)

A, B, Ar _{1 ,} L ₂ , X ₃ , X ₄ , Y ₅ to Y ₈ , and Y ₁₁ to Y ₁₈ are as defined in Formula 1.

The compound represented by the formula (1) may be a compound represented by any one of the following formulas (9) to (11).

In the above formulas (9) to (11)

A, B, Ar _{1 ,} L ₂ , X ₁ , X ₂ , Y ₅ to Y ₈ , and Y ₁₁ to Y ₁₈ are as defined in Formula 1 above.

(*는 화학식 1의 L₁과 결합하는 부위를 의미함)는 하기 A-1 내지 A-18로 표시되는 치환체 중 어느 하나로 표시되는 것이 바람직하다.In the compound represented by the above general formula (1)

Is preferably represented by any one of substituents represented by (* indicates means the region in combination with L ₁ in Formula 1) is A-1 to A-18.

In the above A-1 to A-18,

Ar ₁ is as defined in the above formula (1)

R ₈ are the same or different and are each independently selected from the group consisting of hydrogen, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,

The aryl group and heteroaryl group of R ₈ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and An arylamine group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms, provided that when the substituent is plural, they may be the same or different from each other.

At least one of the plurality of R ₆ is preferably a C ₆ to C ₆₀ aryl group, more preferably a phenyl group.

는 하기 B-1 내지 B-12로 표시되는 치환체 중 어느 하나로 표시되는 것이 바람직하다.In the compound represented by the above formula (1)

Is preferably represented by any one of the substituents represented by the following B-1 to B-12.

In the above B-1 to B-12,

R ₄ to R ₆ are as defined in the above formula (1).

The compound represented by the formula (1) of the present invention described above can be exemplified by the following compounds R1 to R635, but is not limited thereto.

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 the alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

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. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl and the like.

In the present invention, heteroaryl 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, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

In the present invention, aryloxy is a monovalent substituent represented by RO-, and R represents aryl having 6 to 60 carbon atoms. Examples of aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, alkyloxy is a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure can do. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

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

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

In the present invention, heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons, of the ring is N, O, S or Se Lt; / RTI > Examples of heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.

2. Organic Field  Light emitting element

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

More specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above 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 light emitting auxiliary layer, a light emitting layer, a life improving layer, an electron transporting layer and an electron injecting layer. . ≪ / RTI > Specifically, the organic compound layer containing the compound of Formula 1 is preferably a light emitting layer.

The light emitting layer may include a host material (preferably, a phosphorescent host material), wherein the host material may include the compound of the above formula (1). The light emitting layer of the organic electroluminescent device of the present invention may contain 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, and examples thereof include a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, a life improving layer, an electron transporting layer, And may be a sequentially stacked structure. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, and preferably the hole transporting layer, the electron transporting layer, And the like. Further, 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 into the interface between the electrode and the organic layer.

Meanwhile, the organic electroluminescent device of the present invention can be manufactured 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 have.

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 fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet 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.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and ordinary materials known in the art can be used.

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 A1

Under nitrogen gas stream, 10-bromo-7H-benzo [ c] carbazole 5.0g (16.9 mmol), 9-phenyl-9H-carbazole-3-ylboronic acid 5.8g (20.2 mmol), Pd (PPh 3) 4 1.0g (5 and potassium carbonate (7.0 g, 50.6 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A1 (5.6 g, 12.1 mmol, yield 72%).

GC-Mass (theory: 458.55 g / mol, measurement: 458 g / mol)

1H), 8.15 (d, 1H), 8.48 (t, 2H), 10.01 (s, 2H), 7.50-7.67 (m, 1H)

[ Preparation Example  2] Synthesis of A2

A solution of 10.7 g (16.9 mmol) of 7- (10-bromo-7H-benzo [c] carbazole-7-yl) -2,9-diphenylthieno [ 40 ml / 40 ml of Toluene / H ₂ O / Ethanol was added to 4.3 g (20.2 mmol) of Pd (PPh ₃ ) ₄ and 5 g Lt; / RTI >

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the objective compound A2 (8.5 g, 11.8 mmol, yield 70%).

GC-Mass (718.87 g / mol, measured: 718 g / mol)

7H), 8.54 (d, IH), 10.01 (s, IH), 7.42-7.50 (m, )

[ Preparation Example  3] Synthesis of A3

Carbazole-3-ylboronic acid (16.8 mmol), 9- (2,9-diphenylthieno [2,3-f] quinazoline-7-yl) -9H-benzo [ 11.1g (20.2 mmol), Pd ( PPh 3) 4 0.6g (5 mol%), and potassium carbonate 7.0g (50.6 mmol) and insert the _{Toluene / H 2 O / Ethano l80ml} / 40ml / 40ml 3 hours at 110 ℃ Lt; / RTI >

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A3 (8.5 g, 11.8 mmol, yield 70%).

GC-Mass (718.87 g / mol, measured: 718 g / mol)

1H), 8.15 (d, 1H), 8.54 (d, 2H), 10.01 (s, 1H)

[ Preparation Example  4] Synthesis of A4

Under nitrogen gas stream, 10-bromo-7H-benzo [ c] carbazole 5.0g (16.9 mmol), 7-phenyl-7H-benzo [c] carbazole-10-ylboronic acid 6.8g (20.2 mmol), Pd (PPh 3) 4 1.0 g (5 mol%) of potassium carbonate, 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A4 (6.4 g, 12.7 mmol, yield 75%).

GC-Mass (calculated: 508.61 g / mol, measured: 508 g / mol)

2H), 8.50 (d, 2H), 10.01 (s, IH), 7.45-7.63 (m,

[ Preparation Example  5] Synthesis of A5

(2,9-diphenylthieno [2,3-f] quinazoline-7-yl) -7H-benzo [c] carbazole was reacted with 5.0 g (16.9 mmol) of 10-bromo- (10.0 g, 20.2 mmol), Pd (PPh ₃ ) ₄ 1.0 g (5 mol%) and potassium carbonate 7.0 g (50.6 mmol) and Toluene / H ₂ O / Ethanol 80 ml / 40 ml / And the mixture was stirred at 110 DEG C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A5 (9,7 g, 12.7 mmol, yield 75%).

GC-Mass (calculated: 768.92 g / mol, measured: 768 g / mol)

1H), 8.15 (d, 2H), 8.54 (d, 2H), 10.01 (s, 1H)

[ Preparation Example  6] Synthesis of A6

A solution of 10 g of 10-bromo-7H-benzo [c] carbazole (5.0 g, 16.9 mmol), 9- (4,6-diphenylthieno [3,2- d] quinazoline- -3-ylboronic acid 11.6g (20.2 mmol ), Pd (PPh 3) 4 1.0 g (5 mol%) of potassium carbonate, 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A6 (9,7 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 794.96 g / mol, measured: 794 g / mol)

8.05 (d, 1H), 8.15 (d, 3H), 8.54 (d, 2H), 8.04 (d, , 10.01 (s, 1 H)

[ Preparation Example  7] Synthesis of A7

(10.0 mmol) of Pd (PPh ₃ ) ₄ (10.0 mmol) of 10-bromo-7H-benzo [ 1.0 g (5 mol%) of potassium carbonate, 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / Ethano were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A7 (6.5 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 534.65 g / mol, measured: 534 g / mol)

8.13 (d, IH), 8.14 (m, 3H), 8.53 (d, IH) , 10.01 (s, 1 H)

[ Preparation Example  8] Synthesis of A8

9.8 g (16.9 mmol) of 9-phenyl-9 '- (4-phenylquinazolin-2-yl) -9H, 9'H-3,3'-bicarbazole 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were added to a mixture of 13.3 g (20.2 mmol) of Pd (PPh ₃ ) _6, 1.0 g (5 mol% And the mixture was stirred at 110 DEG C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A8 (9.8 g, 11.8 mmol, yield 70%).

GC-Mass (calculated: 827.97 g / mol, measured: 827 g / mol)

1 H-NMR:? 7.25 (m, 1H), 7.43-7.88 (m, 25H), 8.02-8.17 (m, 9H)

[ Preparation Example  9] Synthesis of A9

In a nitrogen atmosphere 2-bromo-5H-benzo [ b] carbazole 5.0g (16.9 mmol) 9-phenyl-9H-carbazole-3-ylboronic acid 5.8g (20.2 mmol), Pd (PPh 3) 4 1.0g (5 mol %), Potassium carbonate (7.0 g, 50.6 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A9 (5.4 g, 11.8 mmol, yield 70%).

GC-Mass (theory: 458.55 g / mol, measurement: 458 g / mol)

1 H-NMR:? 7.28-7.59 (m, 16H), 7.88-7.93 (m, 3H), 8.15 (d,

[ Preparation Example  10] Synthesis of A10

8-bromo-11H-benzo under nitrogen gas stream, [a] carbazole 5.0g (16.9 mmol ), 9-phenyl-9H-carbazole-3-ylboronic acid 5.8g (20.2 mmol), Pd (PPh 3) 4 1.0g (5 and potassium carbonate (7.0 g, 50.6 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the desired compound A10 (5.4 g, 11.8 mmol, yield 70%).

GC-Mass (theory: 458.55 g / mol, measurement: 458 g / mol)

2H), 7.42-7.65 (m, 2H), 7.77-7.84 (m, 3H), 8.12-8.14 10.01 (s, 1 H)

[ Preparation Example  11] Synthesis of A11

8.4 g (16.9 mmol) of 10-bromo-7- (4-phenylquinazolin-2-yl) -7H-benzo [c] carbazole and 6.7 g of 9-phenyl-9H- carbazole-3,6-diyldiboronic acid 2.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours .

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A11 (8.9 g, 12.7 mmol, yield 75%).

GC-Mass (706.60 g / mol, measured: 706 g / mol)

(M, 4H), 8.16-8.18 (m, 4H), 8.54 (m, 2H), 7.45-7.58 d, 1 H)

[ Preparation Example  12] Synthesis of A12

10-bromo-7H-benzo [ c] carbazole 5.0g (16.9 mmol), 9,9-dimethyl-9H-fluoren-2-ylboronic acid 4.8 g (20.2 mmol), Pd (PPh 3) 4 1.0g in a nitrogen atmosphere (5 mol%), potassium carbonate (7.0 g, 50.6 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A12 (5.0 g, 12.1 mmol, yield 72%).

GC-Mass (theory: 409.52 g / mol, measurement: 409 g / mol)

(M, 3H), 7.76 (s, 2H), 7.76-7.79 (m, 2H) , 8.16 (d, IH), 8.54 (d, IH), 10.01 (s, IH)

[ Preparation Example  13] Synthesis of A13

10-bromo-7H-benzo under nitrogen gas stream, [c] carbazole 5.0g (16.9 mmol ), dibenzo [b, d] thiophen-2-ylboronic acid 4.6 g (20.2 mmol), Pd (PPh 3) 4 1.0g (5 and potassium carbonate (7.0 g, 50.6 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A13 (4.7 g, 11.8 mmol, yield 70%).

GC-Mass (theory: 399.51 g / mol, measurement: 399 g / mol)

(M, 2H), 7.65-7.76 (m, 2H), 7.88-7.89 (m, 2H) 49 (d, 2H), 10.01 (s, 1 H)

[ Preparation Example  14] Synthesis of A14

10-bromo-7H-benzo under nitrogen gas stream, [c] carbazole 5.0g (16.9 mmol ), dibenzo [b, d] furane-2-ylboronic acid 4.3 g (20.2 mmol), Pd (PPh 3) 4 1.0g (5 and potassium carbonate (7.0 g, 50.6 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A14 (4.5 g, 11.8 mmol, yield 70%).

GC-Mass (calculated: 383.44 g / mol, measured: 383 g / mol)

1 H-NMR:? 7.35-38 (m, 2H), 7.65-7.85 (m, 12H), 8.15

[ Preparation Example  15] Synthesis of A15

10-bromo-7H-benzo [ c] carbazole 5.0g (16.9 mmol) 9,9'-spirobi [fluorene] -2-ylboronic acid 7.3 g (20.2 mmol), Pd (PPh 3) 4 1.0g in a nitrogen atmosphere ( 5 mol%), potassium carbonate (7.0 g, 50.6 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A15 (9.0 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 531.64 g / mol, measured: 531 g / mol)

8.16 (d, 1H), 8.54 (d, 1H), 10.01 (s, 1H), 7.65-7.75 (m, 1H)

[ Preparation Example  16] Synthesis of A16

Under nitrogen gas stream, 10-bromo-7H-benzo [ c] carbazole 5.0g (16.9 mmol), thianthren-2-ylboronic acid 5.3 g (20.2 mmol), Pd (PPh 3) 4 1.0g (5 mol%), and potassium (50.6 mmol) of Toluene and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A16 (5.2 g, 12.0 mmol, yield 71%).

GC-Mass (calculated: 431.57 g / mol, measured: 431 g / mol)

1H), 8.15 (d, IH), 7.87 (d, IH), 7.87 (d, , 8.54 (d, 1 H), 10.01 (s, 1 H)

[ Preparation Example  17] Synthesis of A17

Under nitrogen gas stream, 10-bromo-7H-benzo [ c] carbazole 5.0g (16.9 mmol), dibenzo [b, e] [1,4] dioxin-2-ylboronic acid 4.6 g (20.2 mmol), Pd (PPh 3) _4, 1.0 g (5 mol%) of potassium carbonate, 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A17 (4.9 g, 12.1 mmol, yield 72%).

GC-Mass (theory: 399.44 g / mol, measurement: 399 g / mol)

(M, 2H), 7.63 (m, 2H), 7.76 (s, 1H), 7.87 (d, 1H), 8.15 (d, 1H), 8.54 (d, 1H), 10.01

[ Preparation Example  18] Synthesis of A18

A solution of 5.0 g (16.9 mmol) of 10-bromo-7H-benzo [c] carbazole, 6.7 g (20.2 mmol) of 9,9-dimethyl-10- _{PPh 3) 4 1.0g (5 mol} %), and potassium carbonate 7.0g (50.6 mmol) and insert the _{Toluene / H 2 O / Ethanol 80ml} / 40ml / 40ml and the mixture was stirred at 110 ℃ for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A18 (6.1 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 500.63 g / mol, measured: 500 g / mol)

(M, 5H), 7.63-7.68 (m, 5H), 7.63-7.68 (m, 4H) 1H), 8.15 (d, 1H), 8.54 (d, 1H), 10.01 (s,

[ Preparation Example  19] Synthesis of A19

9.3 g (16.9 mmol) of 9-phenyl-9H-carbazole-3,6-diyldiboronic acid was added to a solution of 10-bromo-7- (4- phenylbenzo [h] quinazolin- 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / Lt; / RTI >

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A19 (9.2 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 756.66 g / mol, measured: 756 g / mol)

(M, 2H), 7.45-8.12 (m, 27H), 8.16-8.81 (m, 3H), 8.54

[ Preparation Example  20] Synthesis of A20

8.4 g (16.9 mmol) of 9-dimethyl-9H-fluorene-2,7-diyldiboronic acid 5.7 g (16.9 mmol) was added to a solution of 10-bromo-7- , 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / Lt; / RTI >

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A20 (7.8 g, 11.8 mmol, yield 70%).

GC-Mass (calculated: 657.57 g / mol, measured: 657 g / mol)

1H), 7.41 (m, 1H), 7.51 (m, 2H), 7.56 (s, 2H) 1H), 7.64-7.67 (m, 5H), 7.78-8.03 (m, 9H), 8.16-8.81 (m,

[ Synthetic example  1] Synthesis of R41

5.0 g (13.4 mmol) of 7-chloro-2,9-diphenylthieno [2,3-f] quinazoline, 0.6 g (5 mol%) of Pd ₂ (dba) ₃ , - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.3 g (7.9 mmol, R = 65%) of the target compound R41.

GC-Mass (calculated: 794.96 g / mol, measured: 794 g / mol)

[ Synthetic example  2] Synthesis of R42

In a nitrogen stream A1 5.6g (12.1mmol), 3- chloro-1,8-diphenylthieno [3,2-f] quinazoline 5.0g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.3 g (7.9 mmol, R 65%) of the target compound R42.

GC-Mass (calculated: 794.96 g / mol, measured: 794 g / mol)

[ Synthetic example  3] Synthesis of R43

7.2 g (13.4 mmol) of A1, 5.6 g (12.1 mmol) of A1, 9-phenyl-9- _{Pd 2 (dba) 3 0.6g (} 5 mol%), into the tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 7.3 g (7.7 mmol, yield 63%) of the target compound R43.

GC-Mass (calculated: 960.15 g / mol, measured: 960 g / mol)

[ Synthetic example  4] Synthesis of R44

(12.1 mmol) of A1, 7.2 g (13.4 mmol) of 4- (7-chloro-2-phenylthieno [2,3- f] quinazoline-9-yl) -N, N-diphenylaniline, Pd ₂ diba) ₃ , 0.1 g (0.6 mmol) of tri- tert- butylphosphine and 3.5 g (36.4 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 7.1 g (7.4 mmol, yield 61%) of the target compound R44.

GC-Mass (calculated: 962.17 g / mol, measured: 962 g / mol)

[ Synthetic example  5] Synthesis of R45

In a nitrogen stream A3 8.5g (11.8mmol), bromobenzene 2.0g (13.0mmol), Pd 2 (dba) 3 0.7g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 4.1 g (35.4 mmol) of triethylamine and 100 ml of toluene, and the mixture was stirred at 110 DEG C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.1 g (7.7 mmol, yield 65%) of the objective compound R45.

GC-Mass (calculated: 794.96 g / mol, measured: 794 g / mol)

[ Synthetic example  6] Synthesis of R57

In a nitrogen stream A2 8.5g (11.8mmol), 2- chloro-4-phenylquinazoline 3.1g (13.0mmol), Pd 2 (dba) 3 0.7g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) And 4.1 g (35.4 mmol) of sodium tert-butoxide and 100 ml of toluene were placed, and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 7.1 g (7.7 mmol, yield 65%) of the target compound R57.

GC-Mass (calculated: 923.09 g / mol, measured: 923 g / mol)

[ Synthetic example  7] Synthesis of R381

In a nitrogen atmosphere A4 6.4g (12.7mmol), 7- chloro-2,9-diphenylthieno [2,3-f] quinazoline 5.2g (13.9mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.6g (38.0mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 7.1 g (8.4 mmol, yield 66%) of the objective compound R381.

GC-Mass (calculated: 845.02 g / mol, measured: 845 g / mol)

[ Synthetic example  8] Synthesis of R383

(12.7 mmol) of A4, 7.5 g (13.9 mmol) of 7-chloro-2-phenyl-9- (9-phenyl-9H-carbazole- 3- yl) thieno [ 0.6 g (5 mol%) of Pd ₂ (dba) ₃ , 0.1 g (0.6 mmol) of tri- tert- butylphosphine and 3.6 g (38.0 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 8.4 g (8.4 mmol, yield 66%) of the target compound R383.

GC-Mass (theory: 1010.21 g / mol, measurement: 1010 g / mol)

[ Synthetic example  9] Synthesis of R384

(12.7 mmol) of A4, 7.5 g (13.9 mmol) of 4- (7-chloro-2-phenylthieno [2,3-f] quinazoline-9- yl) -N, N- diphenylaniline, Pd ₂ dba) ₃ , 0.1 g (0.6 mmol) of tri- tert- butylphosphine and 3.6 g (38.0 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 8.5 g (8.4 mmol, yield 66%) of the target compound R384.

GC-Mass (calculated: 1012.23 g / mol, measured: 1012 g / mol)

[ Synthetic example  10] Synthesis of R397

In a nitrogen atmosphere A5 9.7g (12.7mmol), 2- chloro-4-phenylquinazoline 3.4g (13.9mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) And 3.6 g (38.0 mmol) of sodium tert-butoxide and 100 ml of toluene were placed, and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 8.0 g (8.2 mmol, yield 65%) of the target compound R397.

GC-Mass (calculated: 973.15 g / mol, measured: 973 g / mol)

[ Synthetic example  11] Synthesis of R399

In a nitrogen atmosphere A5 9.7g (12.7mmol), 2- bromodibenzo [b, d] furane 3.4g (13.9mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6 mmol), 3.6 g (38.0 mmol) of sodium tert-butoxide, and 100 ml of toluene were added, and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 7.3 g (7.8 mmol, yield 62%) of the target compound R399.

GC-Mass (calculated: 935.10 g / mol, measured: 935 g / mol)

[ Synthetic example  12] Synthesis of R542

(12.1 mmol) of A6, 3.4 g (13.9 mmol) of bromobenzene, 0.6 g (5 mol%) of Pd ₂ (dba) ₃ , 0.1 g (0.6 mmol) of tri- tert- butylphosphine and 3.6 g g (38.0 mmol) of triethylamine and 100 ml of toluene, and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.9 g (7.8 mmol, yield 62%) of the target compound R542.

GC-Mass (theory: 871.06 g / mol, measurement: 871 g / mol)

[ Synthetic example  13] Synthesis of R541

In a nitrogen atmosphere A7 6.5g (12.1mmol), 7- chloro-2,9-diphenylthieno [2,3-f] quinazoline 4.4g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - tert -butylphosphine 0.1g (0.6mmol) and put 100ml of Toluene and Sodium tert-butoxide 3.5g (36.4mmol) was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.8 g (7.8 mmol, yield 64%) of the target compound R541.

GC-Mass (theory: 871.06 g / mol, measurement: 871 g / mol)

[ Synthetic example  14] Synthesis of R551

In a nitrogen atmosphere A8 9.8g (11.8mmol), 3- chloro-1,8-diphenylthieno [3,2-f] quinazoline 4.3g (13.0mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 8.4 g (7.2 mmol, yield: 61%) of the target compound R551.

GC-Mass (calculated: 1164.38 g / mol, measured: 1164 g / mol)

[ Synthetic example  15] Synthesis of R141

In a nitrogen atmosphere A9 5.4g (11.8mmol), 7- chloro-2,9-diphenylthieno [2,3-f] quinazoline 4.2g (13.0mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 5.7 g (7.2 mmol, yield 61%) of the target compound R141.

GC-Mass (calculated: 794.96 g / mol, measured: 794 g / mol)

[ Synthetic example  16] Synthesis of R241

In a nitrogen stream A10 5.4g (11.8mmol), 7- chloro-2,9-diphenylthieno [2,3-f] quinazoline 4.8g (13.0mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 5.7 g (7.2 mmol, yield: 61%) of the target compound R241.

GC-Mass (calculated: 794.96 g / mol, measured: 794 g / mol)

[ Synthetic example  17] Synthesis of R556

In a nitrogen stream A11 8.9g (12.7mmol), 3- chloro-1,8-diphenylthieno [3,2-f] quinazoline 4.6g (13.9mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.6g (38.0mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 7.7 g (7.7 mmol, yield 61%) of the target compound R556.

GC-Mass (calculated: 999.19 g / mol, measured: 999 g / mol)

[ Synthetic example  18] Synthesis of R561

5.1 g (13.4 mmol) of 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline and 0.6 g of Pd ₂ (dba) ₃ put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.4 g (7.9 mmol, yield 65%) of the target compound R561.

GC-Mass (theory: 804.98 g / mol, measurement: 804 g / mol)

[ Synthetic example  19] Synthesis of R567

In a nitrogen stream A1 5.6g (12.1mmol), 3- chloro-1,8-diphenylfuro [3,2-f] quinazoline 4.8g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.0 g (7.7 mmol, yield 63%) of the target compound R567.

GC-Mass (calculated: 778.90 g / mol, measured: 778 g / mol)

[ Synthesis Example 20 ] Synthesis of R571

In a nitrogen stream A1 5.6g (12.1mmol), 7- chloro-1,2,9-triphenyl-1H-pyrrolo [2,3-f] quinazoline 5.8g (13.4mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.4 g (7.5 mmol, yield 62%) of the target compound R571.

GC-Mass (calculated: 854.01 g / mol, measured: 854 g / mol)

[ Synthetic example  21] Synthesis of R581

In a nitrogen stream A12 5.0g (12.1mmol), 3- chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.1g (13.4mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.1 g (7.9 mmol, yield 65%) of the target compound R581.

GC-Mass (calculated: 775.94 g / mol, measured: 775 g / mol)

[ Synthetic example  22] Synthesis of R582

In a nitrogen stream A12 5.0g (12.1mmol), 7- chloro-2,9-diphenylfuro [2,3-f] quinazoline 4.8g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 5.6 g (7.7 mmol, yield 63%) of the target compound R582.

GC-Mass (729.86 g / mol, measured: 729 g / mol)

[ Synthesis Example 23 ] Synthesis of R583

In a nitrogen stream A12 5.0g (12.1mmol), 7- chloro-1,2,9-triphenyl-1H-pyrrolo [2,3-f] quinazoline 5.8g (13.4mmol), Pd 2 (dba) 3 0.6g ( 0.1 g (0.6 mmol) of tri- tert- butylphosphine and 3.5 g (36.4 mmol) of sodium tert-butoxide in 100 ml of toluene were placed and the mixture was stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.1 g (7.5 mmol, yield 62%) of the target compound R583.

GC-Mass (theory: 804.98 g / mol, measurement: 804 g / mol)

[ Synthetic example  24] Synthesis of R584

In a nitrogen stream A13 4.7g (11.8mmol), 3- chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.0g (13.0mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 5.7 g (7.7 mmol, yield 65%) of the target compound R584.

 GC-Mass (calculated: 745.93 g / mol, measured: 745 g / mol)

[ Synthetic example  25] Synthesis of R587

In a nitrogen stream A14 4.5g (11.8mmol), 3- chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.0g (13.0mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.4g (35.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 5.6 g (7.7 mmol, yield 65%) of the target compound R587.

GC-Mass (729.86 g / mol, measured: 729 g / mol)

[ Synthetic example  26] Synthesis of R590

In a nitrogen stream A15 6.5g (12.1mmol), 3- chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.1g (13.4mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.9 g (7.9 mmol, yield 65%) of the desired compound R590.

GC-Mass (calculated: 878.07 g / mol, measured: 878 g / mol)

[ Synthetic example  27] Synthesis of R593

In a nitrogen stream A16 5.2g (12.0mmol), 3- chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.0g (13.2mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (35.9mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.1 g (7.8 mmol, yield 65%) of the desired compound R593.

GC-Mass (calculated: 778.00 g / mol, measured: 778 g / mol)

[ Synthetic example  28] Synthesis of R596

5.1 g (13.4 mmol) of 3-chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline and 0.6 g of Pd ₂ (dba) ₃ put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 5.9 g (7.9 mmol, yield 65%) of the target compound R596.

GC-Mass (calculated: 745.85 g / mol, measured: 745 g / mol)

[ Synthetic example  29] Synthesis of R599

In a nitrogen stream A18 6.1g (12.1mmol), 3- chloro-9,9-dimethyl-1,8-diphenyl-9H-cyclopenta [f] quinazoline 5.1g (13.4mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.7 g (7.9 mmol, yield 65%) of the target compound R599.

GC-Mass (calculated: 847.06 g / mol, measured: 847 g / mol)

[ Synthetic example  30] Synthesis of R608

In a nitrogen stream A1 5.6g (12.1mmol), 7- chloro-1,9-diphenyl-1H-pyrazolo [3,4-f] quinazoline 4.8g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol 0.1 g (0.6 mmol) of tri- tert- butylphosphine, 3.5 g (36.4 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.1 g (7.9 mmol, yield 65%) of the target compound R608.

GC-Mass (calculated: 778.90 g / mol, measured: 778 g / mol)

[ Synthetic example  31] Synthesis of R611

In a nitrogen stream A1 5.6g (12.1mmol), 7- chloro-2,9-diphenyloxazolo [4,5-f] quinazoline 4.8g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.2 g (7.9 mmol, yield 65%) of the target compound R611.

GC-Mass (calculated: 779.88 g / mol, measured: 799 g / mol)

[ Synthetic example  32] Synthesis of R614

In a nitrogen stream A1 5.6g (12.1mmol), 7- chloro-1,2,9-triphenyl-1H-imidazo [4,5-f] quinazoline 5.8g (13.4mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.8 g (7.9 mmol, yield 65%) of the target compound R614.

GC-Mass (theory: 854.99 g / mol, measurement: 854 g / mol)

[ Synthetic example  33] Synthesis of R615

In a nitrogen stream A12 5.0g (12.1mmol), 7- chloro-1,9-diphenyl-1H-pyrazolo [3,4-f] quinazoline 4.8g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol 0.1 g (0.6 mmol) of tri- tert- butylphosphine, 3.5 g (36.4 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 5.8 g (7.9 mmol, yield 65%) of the target compound R615.

GC-Mass (729.87 g / mol, measured: 729 g / mol)

[ Synthetic example  34] Synthesis of R616

In a nitrogen stream A12 5.0g (12.1mmol), 7- chloro-2,9-diphenyloxazolo [4,5-f] quinazoline 4.8g (13.4mmol), Pd 2 (dba) 3 0.6g (5 mol%), tri - insert the tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 5.6 g (7.7 mmol, yield 63%) of the target compound R616.

GC-Mass (calculated: 730.85 g / mol, measured: 730 g / mol)

[ Synthetic example  35] Synthesis of R617

In a nitrogen stream A12 5.0g (12.1mmol), 7- chloro-1,2,9-triphenyl-1H-imidazo [4,5-f] quinazoline 5.8g (13.4mmol), Pd 2 (dba) 3 0.6g ( put 5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) and 100ml Toluene was stirred at 110 ℃ for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 6.1 g (7.5 mmol, yield 62%) of the desired compound R617.

GC-Mass (theory: 805.96 g / mol, measurement: 805 g / mol)

[ Synthetic example  36] Synthesis of R621

In a nitrogen stream A19 9.2g (12.1 mmol), 7 -bromo-2,9-diphenylthieno [2,3-f] quinazoline 6.1g (14.5 mmol), Pd (PPh 3) 4 0.7g (5 mol%) and potassium carbonate (7.0 g, 36.3 mmol) was added to Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) and the mixture was stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R621 (9.1 g, 8.7 mmol, yield 72%).

GC-Mass (theory: 1049.25 g / mol, measurement: 1049 g / mol

[ Synthetic example  37] Synthesis of R622

In a nitrogen stream A19 7.8g (11.8 mmol), 7 -bromo-2,9-diphenylthieno [2,3-f] quinazoline 5.9g (14.2 mmol), Pd (PPh 3) 4 0.7g (5 mol%) and potassium carbonitrile (4.9 g, 35.4 mmol) was added to Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) and stirred at 110 ° C for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound R622 (8.1 g, 8.5 mmol, yield 72%).

GC-Mass (calculated: 950.16 g / mol, measured: 950 g / mol)

[ Example  1 to 32] Red organic Field  Fabrication of light emitting device

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 fabricated according to the following procedure.

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 washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / 90% Each compound of Synthesis Examples 1 to 30, 36 and 37 + 10% (piq) ₂ Ir (acac) (300 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  One]

A red organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound R41 as a luminescent host material.

[ Comparative Example  2]

A red organic electroluminescent device was fabricated in the same manner as in Example 1, except that D1 was used instead of the compound R41 as the luminescent host material.

The m-MTDATA, TCTA, (piq ) using ₂ Ir (acac), the structure of the BCP, Alq _3, CBP and D1 are as follows.

[ Evaluation example  One]

The driving voltage, emission peak and current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1 to 32 and Comparative Examples 1 and 2, and the results are shown in the following Table 1 .

Sample Emitting layer host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 R41 4.0 621 16.5 Example 2 R42 4.1 621 16.4 Example 3 R43 4.1 621 17.8 Example 4 R44 4.3 621 17.2 Example 5 R45 4.3 621 16.5 Example 6 R57 4.3 621 17.4 Example 7 R381 4.2 621 17.8 Example 8 R383 4.5 621 17.1 Example 9 R384 4.4 621 17.1 Example 10 R397 4.3 621 16.3 Example 11 R399 4.2 621 17.1 Example 12 R542 4.6 621 15.8 Example 13 R541 4.2 621 15.8 Example 14 R551 4.5 621 15.9 Example 15 R141 4.1 621 16.3 Example 16 R241 4.2 621 18.7 Example 17 R556 4.3 621 17.2 Example 18 R561 4.4 621 16.3 Example 19 R567 4.1 621 18.7 Example 20 R571 4.2 621 19.2 Example 21 R581 3.0 621 15.9 Example 22 R582 3.1 621 17.5 Example 23 R583 3.3 621 15.9 Example 24 R584 3.5 621 15.2 Example 25 R587 3.2 621 16.7 Example 26 R590 3.5 623 15.3 Example 27 R593 3.1 621 16.2 Example 28 R596 3.0 621 16.1 Example 29 R599 3.2 621 17.3 Example 30 R608 3.3 621 15.1 Example 31 R621 3.5 621 16.3 Example 32 R622 3.6 621 15.5 Comparative Example 1 CBP 5.7 622 9.2 Comparative Example 2 D1 4.2 622 14.7

As shown in Table 1, when the compound according to the present invention was used as the light emitting layer material of the red organic electroluminescent device (Examples 1 to 32), when the conventional CBP was used as the light emitting layer material of the red organic electroluminescent device 1), and it was found that the efficiency was superior to that in the case of using D1 as the light emitting layer material of the red organic electroluminescent device (Comparative Example 2).

[ Example  33 to 36] Organic Field  Fabrication of light emitting device

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was ultrasonically cleaned with distilled water. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes And the substrate was transferred to the back vacuum deposition machine.

 (80 nm) / DS-H522 (Doosan Electronics Co., Ltd.) + 5% DS-501 of Synthesis Examples 4, 25, 26 and 28 (m-MTDATA (60 nm)) on the ITO transparent electrode prepared as described above (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).

[ Comparative Example  3]

An organic electroluminescent device was fabricated in the same manner as in Example 33, except that NPB was used in place of the compound R44 used as the hole transport layer material.

The structure of the NPB used is as follows.

[ Evaluation example  2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 33 to 36 and Comparative Example 4, and the results are shown in Table 2 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 33 R44 2.9 22.2 Example 34 R587 3.0 24.5 Example 35 R590 3.6 36.8 Example 36 R596 3.9 34.8 Comparative Example 3 NPB 5.3 18.0

As shown in Table 2, when the compound according to the present invention was used as the hole transport layer material of the organic electroluminescent device (Examples 33 to 36) as the hole transport layer material of the organic electroluminescent device using the conventional NPB The efficiency and the driving voltage were superior to those of Example 3).

[ Example  37 to 43] Organic Field  Manufacturing of light emitting device

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

(80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics Co., Ltd.) (30 nm) / Synthesis Examples 1 and 18 (80 nm) / LiF (1 nm) / Al (200 nm) in the order of 31 to 35 were stacked in this order to prepare an organic electroluminescent device.

[ Comparative Example  4] Organic Field  Manufacturing of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Example 37, except that Alq ₃ was used instead of the compound R41 used as the material of the electron transport layer to deposit at 30 nm.

The structure of the ADN used is as follows.

[ Evaluation example  3]

The driving voltage, current efficiency and emission wavelength at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 37 to 43 and Comparative Example 4, respectively, and the results are shown in Table 3 below.

Sample Electron transport layer The driving voltage (V) Current efficiency (cd / A) Emission peak (nm) Example 37 R41 2.8 9.9 458 Example 38 R561 2.9 9.8 458 Example 39 R611 3.0 9.9 458 Example 40 R614 3.1 10.6 458 Example 41 R615 3.4 11.8 458 Example 42 R616 3.5 12.3 458 Example 43 R617 3.4 13.2 458 Comparative Example 4 Alq ₃ 5.2 5.4 458

As shown in Table 3, when the compound according to the present invention was used as an electron transporting layer material of an organic electroluminescent device (Examples 38 to 43) as a hole transporting layer material of an organic electroluminescent device using conventional Alq ₃ It was found that the efficiency and the driving voltage were superior to those of Comparative Example 4).

Claims (10)

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

In Formula 1,
A is a five-membered ring containing or not containing at least one atom of N, O, S,
B is a 6-membered aromatic ring,
Ar ₁ is selected from the group consisting of hydrogen, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms,
L ₁ and and L ₂ are the same or different, each independently is a single bond, or is selected from the group consisting of a hetero arylene C ₆ ~ C ₆₀ arylene group and a nuclear atoms of 5 to 60, wherein L ₁ is X ₁ , X ₂ , and Y ₁ to Y ₄ ,
X ₁ is NR ₁ or CR ₂ R ₃ ,
X ₂ to X ₄ are the same or different and are each independently a single bond or are selected from the group consisting of S, O, NR ₄ and CR ₅ R ₆ , wherein at least one of X ₂ and X ₄ is a single bond And X ₃ and X ₄ are both a single bond,
Y ₁ to Y ₈ and Y ₁₁ to Y ₁₈ are each independently CR _7, wherein the plurality of R ₇ are the same as or different from each other,
R ₁ to R ₇ are the same or different from each other and each independently selected from the group consisting of hydrogen, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms, or may be bonded to adjacent groups to form a condensed aromatic ring Or a fused heteroaromatic ring,
And won five rings of said A, and 6-membered aromatic ring of B, the aryl group of said Ar _1, a heteroaryl group, an arylene group of said L ₁ and L _2, heteroarylene group, aryl group of the R ₁ to R ₇ group, a heteroaryl group, each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C of ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ cycloalkyl in the group, a number of nuclear atoms of 3 to 40 aryl , 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 ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ An arylamine group, and the like. When the substituent is plural, they may be the same as or different from each other. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (2) to (5).
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,
A, B, Ar _{1 ,} L ₂ , X ₁ to X ₄ , Y ₁ to Y ₈ , and Y ₁₁ to Y ₁₈ are as defined in claim 1. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (6) to (8).
[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas (6) to (8)
A, B, Ar _{1 ,} L ₂ , X ₃ , X ₄ , Y ₅ to Y ₈ , and Y ₁₁ to Y ₁₈ are as defined in claim 1. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (9) to (11).
[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above formulas (9) to (11)
A, B, Ar _{1 ,} L ₂ , X ₁ , X ₂ , Y ₅ to Y ₈ , and Y ₁₁ to Y ₁₈ are as defined in claim 1. The method according to claim 1,
In the formula 1

Would be represented by any of the substituents represented by (* indicates means the region in combination with L ₁ in Formula 1) is A-1 to A-18 in one compound.

In the above A-1 to A-18,
Ar &_lt; 1 > is as defined in claim 1,
R ₈ are the same or different and are each independently selected from the group consisting of hydrogen, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,
The aryl group and heteroaryl group of R ₈ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and An arylamine group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms, provided that when the substituent is plural, they may be the same or different from each other. The method according to claim 1,
A is a five-membered ring containing or not containing at least one atom of N, O, S,
Wherein the 5 membered ring of A is substituted with one or more C ₆ to C ₆₀ aryl groups. The method according to claim 1,
In the formula 1

Is represented by any one of the substituents represented by the following formulas B-1 to B-12.

In the above B-1 to B-12,
R ₄ to R ₆ are as defined in claim 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 a compound according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer. 9. The method of claim 8,
Wherein the organic compound layer containing the compound is a phosphorescent light-emitting layer.