KR101852926B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound used in an organic electroluminescent device, and is characterized by being represented by the following formula (1). When this compound is employed as a dopant compound or a hole transport compound in a light emitting layer, The organic electroluminescent device having excellent light emission characteristics can be realized.
[Chemical Formula 1]

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

The present invention relates to an organic light emitting compound, and more specifically, to an organic light emitting compound which is employed as a dopant compound of a light emitting layer of a light emitting layer of an organic electroluminescent device or a hole transporting compound of a hole transporting functional layer, To an organic electroluminescent device with remarkably improved characteristics.

An organic light emitting phenomenon is a phenomenon that converts electric energy into light energy by using an organic material. An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer from the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material and a charge transporting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color.

On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of stable and efficient organic material layer materials for organic light emitting devices has not yet been sufficiently developed. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

As a blue light emitting material, US Pat. No. 7053255 discloses a blue light emitting compound having a diphenyl anthracene structure and an aryl group substituted at the terminal thereof, and an organic electroluminescent device using the blue light emitting compound, but has a problem in that the light emitting efficiency and brightness are not sufficient . On the other hand, US Pat. No. 7,230,019 and Korean Patent Laid-Open Publication No. 2006-0006760 disclose an organic electroluminescent device using a substituted pyrene compound. However, since the blue color purity is low, It is difficult to implement a full color full color display.

The present invention is to provide a novel organic light emitting compound and an organic electroluminescent device including the organic light emitting compound which can be used as a dopant compound or a hole transporting compound of a hole transporting functional layer in a light emitting layer of an organic electroluminescent device to realize excellent light emitting characteristics.

In order to solve the above-described problems, the present invention provides an organic light-emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device including the same.

[Chemical Formula 1]

The specific structure and substituent of the organic luminescent compound according to the formula 1 will be described later.

The organic electroluminescent device employing the organic electroluminescent compound according to the present invention as a dopant compound of a light emitting layer or a hole transporting compound of a hole transporting layer can realize a further improved luminous efficiency and long life characteristics, And can be used for various display devices.

1 to 5 are cross-sectional views illustrating the structure of an organic electroluminescent device according to an embodiment of the present invention.
6 is a schematic diagram showing the structure of an organic luminescent compound according to the present invention.

Hereinafter, the present invention will be described more specifically.

The present invention relates to a novel organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1)

X is R ₁ -CR ₂ , each of R ₁ and R ₂ independently represents a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted carbon number 3 to 50 heteroaryl groups, preferably a methyl group or a phenyl group.

Ar ₁ to Ar ₄ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 50 carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl substituted or unsubstituted aryl group having 5 to 50 carbon atoms, And a substituted or unsubstituted C2 to C50 heteroaryl group in which one or more ring-opened cycloalkyl having 3 to 30 carbon atoms is fused.

Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or a polycyclic ring, and the alicyclic group, The carbon atom of the polycyclic ring may be substituted with any one or more heteroatoms selected from N, S and O.

A is a substituent that is represented by the following structural formula 1 or structural formula 2:

[Structural formula 1]

[Structural formula 2]

In the structural formula 1 or the structural formula 2,

L is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2 to C50 heteroarylene group in which at least one unsubstituted C1 to C50 arylene group and substituted or unsubstituted C3 to C30 cycloalkyl are fused together and n is 0 to 4 And when n is 2 or more, a plurality of L < ₁ > may be the same or different from each other.

Ar ₅ to Ar ₇ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 50 carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl substituted or unsubstituted aryl group having 5 to 50 carbon atoms, And a substituted or unsubstituted C2 to C50 heteroaryl group in which at least one of the ring-opened cycloalkyls having 3 to 30 carbon atoms is fused.

Ar ₅ and Ar ₆ may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring. The carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may be N, S and < RTI ID = 0.0 > O, < / RTI >

P is an integer of 0 to 3, and when p is 2 or more, a plurality of * - () may be the same or different from each other.

R ₁ , R ₂ , L and Ar ₁ to Ar ₇ may be further substituted with one or more substituents, and the at least one substituent may be hydrogen, deuterium, cyano, halogen, amino, nitro, , A halogenated alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, Group, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms which is substituted or unsubstituted and at least one substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms is fused, and a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms It fused one or more substituted or may be selected from heteroaryl unsubstituted C2 to 50 groups.

In the present invention, examples of the substituents will be specifically described below, but the present invention is not limited thereto.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, A tert-butyl group, a tert-butyl group, a 2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.

In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably in the range of 1 to 30, which does not cause steric hindrance. Specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, a n-butoxy group, an isobutoxy group, a tert- , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n- , A benzyloxy group, a p-methylbenzyloxy group, and the like, but are not limited thereto.

In the present invention, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. [ Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluororanthrene group, but the scope of the present invention is not limited to these examples.

In the present invention, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofurancyl group, a phenanthroline group, An isothiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group and the like, but is not limited thereto.

In the present invention, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a ptert- Anthryloxy group, 2-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, Anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group and the like. Examples of the arylthioxy group include phenylthioxy group, 2- A 4-tert-butylphenyloxy group, and the like. Examples of the arylsulfoxy group include benzene sulfoxy group and p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, Methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo An octyl group, and the like, but are not limited thereto.

In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, But are not limited to, an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group and a triphenylamine group.

In the present invention, the silyl group is specifically exemplified by trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, But are not limited thereto.

In the present invention, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

In the present invention, the alkyloxy group in the alkylthio group and the alkyl group in the alkylsulfoxy group are the same as the aforementioned alkyl groups. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.

In the present invention, the substituted arylene group means a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group. Anthracenyl group and the like are substituted with other substituents.

In the present invention, the substituted heteroarylene group includes a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and condensed heterocyclic groups, Such as a benzoquinoline group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzzcarbazole group, a dibenzothiophenyl group, a dibenzofurane group and the like are substituted with other substituents.

The organic electroluminescent compound according to the present invention represented by the above formula (1) can be used in various organic layers of organic electroluminescent devices due to its structural specificity, and is preferably used as a hole transport compound in a dopant compound or a hole transport layer in a light emitting layer .

Specific examples of the organic luminescent compound represented by formula (1) according to the present invention include, but are not limited to, the following compounds.

An organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituents into the core structure having the above structure can be synthesized. For example, a substance that meets the requirements of each organic material layer can be manufactured by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, and an electron transporting layer material used in manufacturing an organic electroluminescent device into the structure.

In particular, the organic electroluminescent compound represented by Formula 1 according to the present invention has excellent characteristics in terms of efficiency at the time of adoption, driving voltage, and life span in a light emitting layer of an organic electroluminescent device by introducing a substituent into the characteristic core structure, It is confirmed that the organic electroluminescent device can be realized.

The compound of the present invention can be applied to a device according to a conventional method of manufacturing an organic electroluminescent device. The organic electroluminescent device according to one embodiment of the present invention may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic electroluminescent compound according to the present invention may be used for an organic material layer And can be manufactured using conventional device manufacturing methods and materials.

The organic material layer of the organic electroluminescent device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. However, it is not limited to this and may include a smaller number of organic layers.

Therefore, in the organic electroluminescent device of the present invention, the organic material layer may be a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously injecting and transporting holes, a layer simultaneously performing electron injection and electron transporting, And one or more of the above layers may include a compound represented by the formula 1. Preferably, the organic luminescent compound according to the present invention may include a dopant material or a hole transport material May be included as a hole transporting compound in the functional layer.

When the compound represented by Formula 1 is included as a dopant in the light emitting layer, the content of the dopant may be generally selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host. In addition to the organic luminescent compound represented by Formula 1, a host or a dopant compound may be further included, and the content thereof is the same as described above.

In the organic compound layer having such a multilayer structure, the compound represented by the formula (1) may be used in combination with a light emitting layer, a layer that simultaneously transports holes and holes, a layer that simultaneously transports light and emits light, .

For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.

1 shows an organic electronic device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially laminated on a substrate 1 Structure is illustrated. In this structure, the compound represented by the formula (1) may be included in the hole injection layer (3), the hole transport layer (4), the light emitting layer (5) or the electron transport layer (6).

2 shows the structure of an organic electronic device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5 and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by the formula (1) may be included in the hole injection layer (3), the hole transport layer (4), or the electron transport layer (6).

3 illustrates the structure of an organic electronic device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially stacked on a substrate 1. In such a structure, the compound represented by the formula (1) may be included in the hole transport layer (4), the light emitting layer (5), or the electron transport layer (6).

4 illustrates the structure of an organic electronic device in which an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound represented by the formula (1) may be included in the light-emitting layer (5) or the electron-transporting layer (6).

5 illustrates the structure of an organic electronic device in which an anode 2, a light-emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1. As shown in Fig. In such a structure, the compound represented by the formula (1) may be included in the luminescent layer (5).

For example, the organic electroluminescent device according to the present invention can be manufactured by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal oxide or a conductive metal oxide on the substrate, An anode is formed by depositing an alloy on the anode, and an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and then a substance usable as a cathode is deposited thereon.

In addition to such a method, an organic electroluminescent device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) metal oxides, ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) , Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof; a multilayer such as LiF / Al or LiO ₂ / Structural materials, and the like, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazol-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and A benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, and the like.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable. Specific examples thereof include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex.

The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

In addition, the organic electroluminescent compound according to the present invention can act on a principle similar to that applied to an organic electroluminescent device in an organic electronic device including an organic solar cell, an organophotoreceptor, an organic transistor and the like.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

Example  1: Synthesis of compound 1

(One) Manufacturing example  1: Synthesis of Intermediate 1-0

(1.9 g, 0.010 mol), 1-chloro-3-iodobenzene (2.4 g, 0.010 mol), Pd (dba) 3 (0.1 g, 0.001 mol) and P -Bu) 3 (0.04 g, 0.0002 mol) and STBT (2.9 g, 0.030 mol) were added 70 mL of toluene and the mixture was stirred under reflux. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: EA, followed by column purification (N-HEXANE: MC) to obtain <Intermediate 1-0> 1.8 g (yield 62%). (m / z = 296)

(2) Manufacturing example  2: Synthesis of intermediate 1-1

Intermediate 1-0 (2.3 g, 0.010 mol) was added, and THF (30 mL) was added thereto. The mixture was stirred and dissolved, and the temperature was lowered to 0 ° C. CH3MgBr dissolved in THF was slowly added thereto, the temperature was slowly raised to room temperature, and the mixture was stirred for 5 hours. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: EA, followed by column purification (N-HEXANE: MC) to obtain 2.0 g (yield 73%) of Intermediate 1-1. (m / z = 280)

(3) Manufacturing example  3: Synthesis of intermediate 1-2

Intermediate 1-1 (2.8 g, 0.010 mol) was added thereto, and a small amount of H2SO4 was added at room temperature, followed by stirring for 5 hours. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: EA and then subjected to column purification (N-HEXANE: MC) to obtain <Intermediate 1-2> (1.7 g, yield 62%). (m / z = 278)

(4) Manufacturing example  4: Synthesis of intermediate 1-3

100 mL of toluene was added to bromobenzene (1.7 g, 0.011 mol), Pd (dba) 2 (0.5 g, 0.0005 mol) and sodium tert-butoxide (1.9 g, 0.020 mol) And the mixture was reacted at 95 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC, followed by column purification (N-HEXANE: MC) to obtain 2.2 g (yield 62%) of Intermediate 1-1. (m / z = 354)

(5) Manufacturing example  5: Synthesis of Compound 1

2.0 g (yield 70%) of <compound 1> was obtained by synthesizing diphenylamine (3.7 g, 0.022 mol) in Intermediate 1-3 (3.5 g, 0.010 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (6.80 / d, 5.91 / d, 5.69 / d, 1.72 / s) 5H (6.81 / m) 10H (7.20 / m, 6.63 / d)

LC / MS: m / z = 620 [(M + 1) ^&lt; ^{+ &}

Example  2: Synthesis of compound 2

(One) Manufacturing example  1: Synthesis of intermediate 2-1

(1.2 g, 0.011 mol) was added to 1-bromo-4-phenylnaphthalene (2.8 g, 0.010 mol) in the same manner as in Example 1- (Yield: 56%). (m / z = 309)

(2) Manufacturing example  2: Synthesis of Compound 2

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 2-1 (6.8 g, 0.022 mol) was added to intermediate 1-3 (3.5 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (6.81 / m) 2H (8.49 / d, 8.07 / d, 7.78 / d, 7.54 / m, 7.53 / m, 7.41 / m, 7.20 / m, 7.04 d, 6.81 / d, 6.63 / d, 5.91 / d, 5.69 / s, 2.34 / s, 1.72 / s)

LC / MS: m / z = 901 [(M + 1) ^&lt; ^{+ &}

Example  3: Synthesis of compound 3

(One) Manufacturing example  1: Intermediate 3-1 Synthesis

Synthesis was conducted in the same manner as in Example 1 (4) except that 4-bromodibenzo [b, d] thiophene (2.9 g, 0.011 mol) was added to 3,5-dimethylaniline (1.2 g, 0.010 mol) 1 &gt; 1.5 g (yield: 51%). (m / z = 303)

(2) Manufacturing example  2: Synthesis of Compound 3

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4) to give Intermediate 3-1 (6.7 g, 0.022 mol) and Intermediate 1-3 (3.5 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (6.81 / m) 2H (8.45 / d, 7.98 / d, 7.81 / d, 7.52 / m, 7.50 / m, 7.27 / m, 7.20 / m, 6.86 s), 4H (6.36 / s, 2.34 / s), 6.71 / s, 6.71 /

LC / MS: m / z = 889 [(M + 1) ^&lt; ^{+ &}

Example  4: Synthesis of compound 4

(One) Manufacturing example  1: Synthesis of Intermediate 4-1

Synthesis was conducted in the same manner as in Example 1 (4) except that 1-bromo-4-methylbenzene (1.9 g, 0.011 mol) was added to Intermediate 1-2 (2.8 g, 0.010 mol) g (yield 66%). (m / z = 368)

(2) Manufacturing example  2: Synthesis of intermediate 4-2

(4-bromophenyl) trimethylsilane (2.5 g, 0.011 mol) was added to 3,5-dimethylaniline (1.2 g, 0.010 mol) g (yield: 56%). (m / z = 269)

(3) Manufacturing example  3: Synthesis of Compound 4

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 4-2 (5.9 g, 0.022 mol) was added to Intermediate 4-1 (3.7 g, 0.010 mol) ). (m / z = 295)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (6.98 / d, 6.80 / d, 6.71 / s, 6.51 / d, 5.91 / d, 5.69 / s, 1.72 / s) 4H (7.15 / d, 6.61 / d, 6.36 / d) 5H (2.34 / s) 6H (0.25 / s)

LC / MS: m / z = 835 [(M + 1) ^&lt; ^{+ &}

Example  5: Synthesis of compound 5

(One) Manufacturing example  1: Synthesis of intermediate 5-1

(Intermediate 5-1) was synthesized in the same manner as in Example 1 (4) except that 4-tert-butylaniline (1.7 g, 0.011 mol) was added to 1-bromo-4-isocyanobenzene (1.8 g, 0.010 mol) 1.7 g (yield 67%) was obtained. (m / z = 250)

(2) Manufacturing example  2: Synthesis of compound 5

4.3 g (yield: 63%) of compound 5 was synthesized in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 5-1 (5.5 g, 0.022 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (6.81 / m) 2H (7.20 / m, 6.80 / d, 6.63 / d, 5.91 / d, 5.69 / s, 1.72 / s) 4H (7.39 / d , 7.01 / d, 6.81 / d, 6.55 / d) 6H (1.35 / s)

LC / MS: m / z = 783 [(M + 1) ^&lt; ^{+ &}

Example  6: Synthesis of Compound 6

(One) Manufacturing example  1: Synthesis of intermediate 6-1

(2.5 g, 0.011 mol) was added to Intermediate 1-2 (2.8 g, 0.010 mol), and 2.8 g (yield: 66%) of Intermediate 6-1 was synthesized in the same manner as in Example 1- %). (m / z = 430)

(2) Manufacturing example  2: Synthesis of Compound 6

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 3-1 (6.6 g, 0.022 mol) was added to Intermediate 6-1 (4.3 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.41 / m) 2H (8.45 / d, 7.98 / d, 7.81 / d, 7.54 / d, 7.52 / d, 7.52 / m, 7.51 / m, 7.50 d, 6.71 / s, 6.69 / d, 5.91 / d, 5.69 / s, 1.72 / s) 4H (6.36 / d, 2.34 / s)

LC / MS: m / z = 965 [(M + 1) ^&lt; ^{+ &}

Example  7: Synthesis of Compound 7

(One) Manufacturing example  1: Synthesis of Compound 7

4.5 g (yield: 73%) of Compound 7 was synthesized in the same manner as in Example 1 (4) except that 9H-carbazole (3.7 g, 0.022 mol) was added to Intermediate 1-3 &Lt; / RTI >

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (6.81 / m) 2H (8.55 / d, 8.12 / d, 7.94 / d, 7.63 / d, 7.50 / m, 7.33 / m, 7.29 / m, 7.25 / m, 7.20 / m, 7.05 / d, 6.64 / d, 6.63 / d, 6.40 / s, 1.72 / s)

LC / MS: m / z = 616 [(M + 1) ^&lt; ^{+ &}

Example  8: Compound 8 Synthesis

(One) Manufacturing example  1: Synthesis of Intermediate 8-1

To 1.4 g (0.012 mol) of phenylboronic acid, Pd (PPh3) 4 (0.6 g, 0.0005 mol) and potassium carbonate (2.8 g, 0.020 mol) in THF 100 mL, and the mixture was reacted at 65 ° C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC, and subjected to column purification (N-HEXANE: MC) to obtain 2.0 g (yield: 51%) of Intermediate 7-2. (m / z = 395)

(2) Manufacturing example  2: Synthesis of Intermediate 8-2

2-bromo-4,6-diphenyl-1,3,5-triazine (3.4 g, 0.011 mol), NaH (0.8 g, 0.011 mol) was added to 11,12-dihydroindolo [2,3- , 0.030 mol) was added 80 mL of DMF and stirred for 12 hours. After the completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC, followed by column purification (N-HEXANE: MC) to obtain 2.3 g (yield: 47%) of Intermediate 8-2. (m / z = 487)

(3) Manufacturing example  3: Synthesis of Compound 8

4.5 g (yield: 53%) of Compound 8 was synthesized in the same manner as in Example 1- (4), except that Intermediate 8-1 (4.0 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.12 / d, 7.57 / d, 7.05 / d, 6.64 / d, 6.40 / s) 2H (8.55 / d, 7.94 / d, 7.52 / d, 7.33 m, 7.25 / m, 7.20 / m, 6.81 / m, 6.63 / d, 1.72 / s) 3H (7.41 /

LC / MS: m / z = 848 [(M + 1) ^&lt; ^{+ &}

Example  9: Synthesis of Compound 9

(One) Manufacturing example  1: Synthesis of intermediate 9-1

Was synthesized in the same manner as in Example 8- Preparation Example (1), except that phenyl boronic acid (1.4 g, 0.012 mol) was added to 2,4,6-tribromo-1,3,5-triazine (3.2 g, 0.010 mol) 1.9 g (yield: 61%) of Intermediate 9-1 was obtained. (m / z = 314)

(2) Manufacturing example  2: Synthesis of intermediate 9-2

Intermediate 9-2 was synthesized in the same manner as in Example 8- (1) except that biphenyl-4-ylboronic acid (2.4 g, 0.012 mol) was added to Intermediate 9-1 (3.1 g, 0.010 mol) (Yield: 65%). (m / z = 388)

(3) Manufacturing example  3: Synthesis of intermediate 9-3

Intermediate 9-2 (4.3 g, 0.011 mol) was added to Intermediate 1-2 (2.8 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 8- 58%). (m / z = 585)

(4) Manufacturing example  4: Synthesis of intermediate 9-4

Synthesis was conducted in the same manner as in Example 8- (1) except that phenyl boronic acid (1.4 g, 0.012 mol) was added to Intermediate 9-3 (5.9 g, 0.010 mol) %). (m / z = 627)

(5) Manufacturing example  5: Synthesis of intermediate 9-5

Synthesis was conducted in the same manner as in Example 1 (4) except that bromobenzene (1.7 g, 0.011 mol) was added to 11,12-dihydroindolo [2,3-a] carbazole (2.6 g, 0.010 mol) 5> 1.6 g (yield: 49%). (m / z = 332)

(6) Manufacturing example  6: Synthesis of Compound 9

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 9-5 (3.6 g, 0.011 mol) was added to Intermediate 9-4 (6.3 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.12 / d, 7.57 / d, 7.45 / m, 7.11 / d, 6.81 / s, 6.73 / d, 6.64 / d, 6.40 / s) 2H (8.55 m), 7.25 / d, 1.72 / s), 3H (7.41 / m), 4H (7.52 / d, 7.38 / d, 8.28 / d, 7.94 / d, 7.85 / d, 7.58 / ) 6H (7.51 / m)

LC / MS: m / z = 924 [(M + 1) ^&lt; ^{+ &}

Example  10: Compound 10 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 10-1

Synthesis was conducted in the same manner as in Example 8- (1) except that naphthalen-1-ylboronic acid (2.0 g, 0.012 mol) was added to 9,10-dibromoanthracene (3.4 g, 0.010 mol) g (yield: 54%). (m / z = 383)

(2) Manufacturing example  2: Synthesis of intermediate 10-2

Intermediate 10-1 (4.2 g, 0.011 mol) was added to Intermediate 1-2 (2.8 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 1- (4) 71%). (m / z = 580)

(3) Manufacturing example  3: Synthesis of compound 10

4.5 g (yield 68%) of Compound 10 was synthesized in the same manner as in Example 8- (1) except that phenyl boronic acid (2.8 g, 0.024 mol) was added to Intermediate 10-2 (5.8 g, &Lt; / RTI > (m / z = 333)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.42 / d, 8.08 / d, 8.04 / d, 7.61 / m) 2H (7.91 / d, 7.90 / d, 7.55 / m, 7.41 d, 7.51 / m, 7.39 / m, 7.38 / d, 7.11 / d, 6.81 /

LC / MS: m / z = 664 [(M + 1) ^&lt; ^{+ &}

Example  11: Compound 11 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 11-1

Boronic acid (1.4 g, 0.012 mol) was added to 4-bromo-naphthalen-1-ol (2.2 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 8- 1> 1.6 g (yield: 73%). (m / z = 220)

(2) Manufacturing example  2: Synthesis of intermediate 11-2

100 mL of methyl chloride was added to trifluoromethane sulfonic anhydride (3.1 g, 0.011 mol), pyridine (1.0 g, 0.013 mol) and potassium carbonate (4.1 g, 0.030 mol) Lt; / RTI &gt; After completion of the reaction, the reaction mixture was cooled, and the product was separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 2.5 g (m / z = 352)

(3) Manufacturing example  3: Synthesis of intermediate 11-3

1.5 g (yield: 51%) of Intermediate 11-3 was synthesized in the same manner as in Example 1 (4) except that aniline (1.0 g, 0.011 mol) was added to Intermediate 11-2 (3.5 g, 0.010 mol) &Lt; / RTI > (m / z = 295)

(4) Manufacturing example  4: Synthesis of intermediate 11-4

Synthesis was conducted in the same manner as in Example 1 (4), except that 1,4-dibromobenzene (2.6 g, 0.011 mol) was added to Intermediate 11-3 (3.0 g, 0.010 mol) Yield: 53%). (m / z = 450)

(5) Manufacturing example  5: Synthesis of intermediate 11-5

Intermediate 11-4 (5.0 g, 0.011 mol) was added to Intermediate 1-2 (2.8 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 1- (4) 66%). (m / z = 647)

(6) Manufacturing example  6: Synthesis of Compound 11

6.0 g (Yield: 66%) of Compound 11 was synthesized in the same manner as Example 1-Preparation Example (4), except that 9H-carbazole (3.7 g, 0.022 mol) was added to Intermediate 11-5 (6.5 g, &Lt; / RTI >

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.43 / d, 7.85 / d, 7.46 / m, 7.41 / m, 7.32 / m, 6.99 / s, 6.81 / m, 6.76 / s) 2H (8.55 m, 7.29 / m, 7.25 / m, 7.20 / m, 7.05 / d, 6.64 / d , 6.63 / d, 6.40 / s, 1.72 / s) 4H (6.38 / d)

LC / MS: m / z = 910 [(M + 1) ^&lt; ^{+ &}

Example  12: Compound 12 Synthesis

(One) Manufacturing example  1: Synthesis of Intermediate 12-1

Synthesis was conducted in the same manner as in Example 1 (4) except that 3-bromo-9-phenyl-9H-carbazole (3.5 g, 0.011 mol) was added to Intermediate 1-2 (2.8 g, 0.010 mol) -1> 3.7 g (yield 72%). (m / z &lt; / RTI &gt; = 519)

(2) Manufacturing example  2: Synthesis of Compound 12

The compound 12 was synthesized in the same manner as in Example 1 (4) except that 2-phenyl-1H-indole (4.2 g, 0.022 mol) was added to Intermediate 12-1 (5.2 g, 0.010 mol) Yield: 58%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 7.45 / m, 7.38 / d, 7.25 / m, 6.77 / d, 6.75 / s) 2H (7.93 / d, 7.58 / m, 7.50 d, 7.41 / m, 7.05 / d, 6.87 / m, 6.64 / d, 6.60 / s, 6.40 / s, 1.72 / s) )

LC / MS: m / z = 833 [(M + 1) ^&lt; ^{+ &}

Example  13: Compound 13 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 13-1

Synthesis was conducted in the same manner as in Example 1 (4) except that 4-bromo-N, N-dip-tolylaniline (3.9 g, 0.011 mol) was added to Intermediate 1-2 (2.8 g, 0.010 mol) -1> 3.6 g (yield 66%). (m / z = 549)

(2) Manufacturing example  2: Synthesis of Compound 13

The compound was synthesized in the same manner as in Example 1 (4) except that 9H-pyrido [3,4-b] indole (3.7 g, 0.022 mol) was added to Intermediate 13-1 (5.5 g, 0.010 mol) > 4.8 g (yield: 59%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.87 / s, 8.55 / d, 8.43 / d, 7.94 / d, 7.38 / d, 7.33 / m, 7.25 / m, 7.05 / d, 6.64 / d , 6.40 / s, 2.34 / s, 1.72 / s) 4H (6.98 / d, 6.51 / d, 6.38 / d)

LC / MS: m / z = 814 [(M + 1) ^&lt; ^{+ &}

Example  14: Compound 14 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 14-1

2.1 g (Intermediate 14-1) (yield: 2.1 g) was obtained by the same method as in the preparation example (1) of Example 8, except that phenyl boronic acid (2.8 g, 0.024 mol) 59%). (m / z = 361)

(2) Manufacturing example  2: Synthesis of intermediate 14-2

1.3 g of Intermediate 14-2 was synthesized in the same manner as in Example 8- (1) except that phenyl boronic acid (1.4 g, 0.012 mol) was added to 3-bromonaphthalen-1-ol (2.2 g, 0.010 mol) (Yield: 59%). (m / z = 220)

(3) Manufacturing example  3: Synthesis of intermediate 14-3

Synthesis was conducted in the same manner as in Example 11- (2) except that trifluoromethane sulfonic anhydride (3.1 g, 0.011 mol) and pyridine (1.0 g, 0.013 mol) were added to Intermediate 14-2 (2.2 g, 0.010 mol) 14-3> 2.4 g (yield 67%). (m / z = 352)

(4) Manufacturing example  4: Synthesis of intermediate 14-4

To a solution of bis (pinacolato) dibron (5.0 g, 0.024 mol), PdCl 2 (dppf) (0.4 g, 0.0005 mol) and potassium acetate (2.7 g, 0.020 mol) in 9,10-dibromoanthracene (3.4 g, 0.010 mol) , And 4-dioxane (100 mL) were added and the mixture was reacted for 24 hours at 95 ° C. After completion of the reaction, the reaction mixture was cooled and separated into H 2 O: MC and purified by column chromatography (n-hexane: MC) . (m / z = 430)

(5) Manufacturing example  5: Synthesis of intermediate 14-5

Intermediate 14-4 (5.2 g, 0.012 mol) was added to Intermediate 14-3 (3.5 g, 0.010 mol) and synthesized in the same manner as in Example 8- 64%). (m / z = 506)

(6) Manufacturing example  6: Synthesis of Intermediate 14-6

Intermediate 14-6 was synthesized in the same manner as in Example 8- (1) except that 1,4-dibromobenzene (2.4 g, 0.010 mol) was added to Intermediate 14-5 (6.1 g, 0.012 mol) Yield: 64%). (m / z = 535)

(7) Manufacturing example  7: Synthesis of Compound 14

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 14-6 (5.9 g, 0.011 mol) was added to Intermediate 14-1 (3.6 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.08 / d, 7.85 / s, 7.76 / s) 2H (7.55 / m, 7.54 / d, 7.11 / d, 6.81 / s, 6.73 (7.51 / d, 7.31 / m) 6H (7.52 / d, 7.51 / m)

LC / MS: m / z = 817 [(M + 1) ^&lt; ^{+ &}

Example  15: Compound 15 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 15-1

2.0 g (0.011 mol) of 1-bromo-4-isopropylbenzene was added to 4-chloroaniline (1.3 g, 0.010 mol) (Yield: 55%). (m / z = 363)

(2) Manufacturing example  2: Synthesis of compound 15

3.5 g (yield: 51%) of compound 15 was synthesized in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 14-1 (3.6 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.41 / m, 7.11 / d, 6.81 / s, 6.73 / d, 2.87 / s, 1.72 / s) 4H (7.52 / d, 7.51 / m, 7.05 / d, 6.55 / d, 6.38 / d, 1.20 / s)

LC / MS: m / z = 689 [(M + 1) ^&lt; ^{+ &}

Example  16: Compound 16 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 16-1

Dibromobenzene (2.6 g, 0.011 mol) was added to 3,6-diphenyl-9H-carbazole (3.2 g, 0.010 mol) in the same manner as in Example 1- 1> 2.9 g (yield: 62%). (m / z &lt; / RTI &gt; = 474)

(2) Manufacturing example  2: Synthesis of Compound 16

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4) to obtain Intermediate 16-1 (5.2 g, 0.011 mol) and Intermediate 14-1 (3.6 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (7.77 / s, 7.37 / d, 7.11 / d, 6.81 / s, 6.73 / d, 6.63 / d, 1.72 / s) 4H (7.41 / m) 8H (7.52 / d, 7.51 /

LC / MS: m / z = 755 [(M + 1) ^&lt; ^{+ &}

Example  17: Compound 17 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 17-1

Intermediate 17-1 was synthesized in the same manner as in Example 14- (4) except that bis (pinacolato) dibron (2.5 g, 0.012 mol) was added to 9-bromo-10-phenylanthracene (3.3 g, 0.010 mol) 2.4 g (yield: 63%) was obtained. (m / z = 380)

(2) Manufacturing example  2: Synthesis of intermediate 17-2

Synthesis was conducted in the same manner as in Example 8- (1) except that 2,5-dichloro-4,6-dimethylpyrimidine (1.9 g, 0.011 mol) was added to Intermediate 17-1 (3.8 g, 0.010 mol) -2> 2.1 g (yield 54%). (m / z = 394)

(3) Manufacturing example  3: Synthesis of Compound 17

Compound (17) (4.0 g, yield 55%) was synthesized in the same manner as in Example 8 (2) except that Intermediate 17-2 (4.3 g, 0.011 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.11 / d, 6.81 / s, 6.73 / d, 2.33 / s, 1.72 / s) 3H (7.41 / m) 4H (7.91 / d, 7.39 / m ) 6H (7.52 / d, 7.51 / m)

LC / MS: m / z = 720 [(M + 1) ^&lt; ^{+ &}

Example  18: Compound 18 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 18-1

2.0 g (yield: 62%) of Intermediate 18-1 was synthesized in the same manner as in PREPARATION 1-PREPARATION (4), except that 3,5-dibromophenylboronic acid (3.1 g, 0.011 mol) %). (m / z = 323)

(2) Manufacturing example  2: Synthesis of intermediate 18-2

(4-bromo-3,5-dimethylphenyl) trimethyl silane (2.6 g, 0.010 mol) was added to Intermediate 18-1 (3.8 g, 0.012 mol) 2.5 g (yield: 55%) of Intermediate 18-2 was obtained. (m / z = 456)

(3) Manufacturing example  3: Synthesis of compound 18

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 18-2 (5.0 g, 0.011 mol) was added to Intermediate 14-1 (3.6 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.41 / m, 7.31 / s, 7.31 / d, 6.81 / m, 6.81 / s, 6.73 / d, 6.25 / s, 2.59 / s, 1.72 / s ) 3H (0.25 / s) 4H (7.52 / d, 7.51 / m, 7.20 /

LC / MS: m / z = 782 [(M + 1) ^&lt; ^{+ &}

Example  19: Compound 19 Synthesis

(One) Manufacturing example  1: Synthesis of Compound 19

Compound 1 (6.2 g, 0.010 mol) was dissolved in 60 mL of THF, cooled to 0 ° C., and then phenyl magnesium bromide (4.5 g, 0.025 mol) was added slowly. Thereafter, the temperature was slowly raised to room temperature, and then the mixture was stirred for 12 hours to add distilled water, and the reaction was terminated. Then, the organic layer was extracted with EA and purified by column (N-HEXANE: MC) to obtain 4.2 g (yield: 57%) of Compound 19.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (7.26 / m, 5.65 / s) 4H (7.33 / m, 7.11 / d) 5H (6.81 / m) 10H (7.20 / m, 6.63 / d)

LC / MS: m / z = 744 [(M + 1) ^&lt; ^{+ &}

Example  20: Compound 20 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 20-1

Synthesis was carried out in the same manner as in Example 1 (4) except that 4-bromodibenzo [b, d] furan (2.7 g, 0.011 mol) was added to 3,5-dimethylaniline (1.2 g, 0.010 mol) 1> 1.9 g (yield 67%). (m / z = 287)

(2) Manufacturing example  2: Synthesis of intermediate 20-2

Intermediate 20-1 was obtained in a yield of 5.2 g (yield: 82%) in the same manner as in Example 1 (4) except that Intermediate 20-1 (6.3 g, 0.022 mol) 61%). (m / z = 856)

(3) Manufacturing example  3: Synthesis of Compound 20

Compound (20) (5.4 g, yield 55%) was synthesized in the same manner as in PREPARATION 19- PREPARATION (1) except that phenylmagnesium bromide (4.5 g, 0.025 mol) was added to intermediate 20-2 (8.6 g, 0.010 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (6.81 / m) 2H (7.89 / d, 7.66 / d, 7.38 / m, 7.32 / m, 7.26 / m, 7.25 / d, 7.20 / m, 7.07 (7.33 / m, 7.11 / d, 6.36 / s, 2.34 / s)

LC / MS: m / z = 981 [(M + 1) ^&lt; ^{+ &}

Example  21: Compound 21 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 15-1

(4-bromophenyl) trimethylsilane (2.5 g, 0.011 mol) was added to p-toluidine (1.1 g, 0.010 mol) Yield: 65%). (m / z = 255)

(2) Manufacturing example  2: Synthesis of intermediate 21-2

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4) to give Intermediate 21-1 (5.6 g, 0.022 mol) and Intermediate 6-1 (9.8 g, 0.020 mol) ). (m / z = 430)

(3) Manufacturing example  3: Synthesis of Compound 21

5.9 g (Yield: 59%) of Compound 21 was synthesized in the same manner as in Example 19- (1) except that phenylmagnesium bromide (4.5 g, 0.025 mol) was added to Intermediate 21-2 (4.4 g, 0.010 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.41 / m) 2H (7.52 / d, 7.51 / m, 7.26 / m, 6.73 / d, 5.87 / d, 5.65 / s, 2.34 / s) 4H (7.33 / m, 7.15 / d, 7.11 / d, 6.98 / d, 6.61 / d, 6.51 / d)

LC / MS: m / z = 993 [(M + 1) ^&lt; ^{+ &}

Example  22: Compound 22 Synthesis

(One) Manufacturing example  1: Synthesis of Compound 22

Compound 21 was obtained in an amount of 3.5 g (yield: 47%) by the same method as in PREPARATION 19-PREPARATION (1) except that phenylmagnesium bromide (4.5 g, 0.025 mol) was added to compound 7 (6.2 g, 0.010 mol).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (6.81 / m) 2H (8.55 / d, 8.12 / d, 7.94 / d, 7.63 / d, 7.50 / m, 7.33 / m, 7.29 / m, 7.26 d), 6.30 (d), 6.30 (d), 6.30 (d, 6H)

LC / MS: m / z = 740 [(M + 1) ^&lt; ^{+ &}

Example  23: Compound 23 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 23-1

Intermediate 11-1 (3.9 g, 0.011 mol) was added to 4- (trimethylsilyl) aniline (1.7 g, 0.010 mol) (Yield: 51%). (m / z = 367)

(2) Manufacturing example  2: Synthesis of intermediate 23-2

(2.7 g, 0.011 mol) was added to Intermediate 23-1 (3.7 g, 0.010 mol) in the same manner as in Example 1 (4) to give 2.8 g of Intermediate 23-2 Yield: 54%). (m / z = 522)

(3) Manufacturing example  3: Synthesis of intermediate 23-3

Intermediate 23-2 (5.7 g, 0.011 mol) was added to Intermediate 14-1 (3.6 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 1- (4) 57%). (m / z = 803)

(4) Manufacturing example  4: Synthesis of Compound 23

5.2 g (yield: 56%) of compound 23 was synthesized in the same manner as in PREPARATION 19- PREPARATION EXAMPLE 1, except that phenylmagnesium bromide (4.5 g, 0.025 mol) was added to Intermediate 23-3 (8.0 g, 0.010 mol) .

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.43 / d, 7.85 / d, 7.46 / m, 7.32 / m, 6.99 / s, 6.76 / s) 2H (7.79 / d, 7.26 / m, 7.15 6H (7.51 / m), 6H (7.41 / m, 0.25 / s), 4H (7.52 / d, 7.33 / m, 7.11 / d, 6.38 / d)

LC / MS: m / z = 928 [(M + 1) ^&lt; ^{+ &}

device Example  1: Compound 4 The light-  Neon blue Dopant  Used as a material abandonment Fabrication of electroluminescent device

The ITO transparent electrode (anode) was subjected to ultrasonic cleaning for 5 minutes in isopropyl-alcohol, followed by UV ozone cleaning for 30 minutes. A glass substrate on which a transparent electrode line after cleaning was formed was mounted on a substrate holder of a vacuum evaporation apparatus. First, CuPc (30 nm) was deposited as a hole injecting material on the side where the transparent electrode line was formed to cover the transparent electrode. NPB (80 nm) was deposited thereon as a hole transporting material, and then Compound A: Compound 4 was deposited at a mass ratio of 20: 1 to form a light emitting layer having a thickness of 30 nm. After that, Alq3 (5 nm) and LiF (1 nm) were formed as an electron injecting material, and a negative electrode was formed with Al (80 nm).

device Example  2 to 13

Organic electroluminescent devices of Device Examples 2 to 13 were fabricated in the same manner as in Example 1 except that the compound described in [Table 1] was used in place of the compound 4 described above.

device Comparative Example  One

The organic electroluminescent device for Comparative Example 1 was fabricated in the same manner except that Compound B, which is generally used as a fluorescent dopant material, was used in place of the compound prepared by the invention in the device structure of the embodiment.

device Example  14: Compound 1 The electronic layer  Blocking With hole transport material  Employed U Manufacture of electro-optical optical devices

The ITO transparent electrode (anode) was subjected to ultrasonic cleaning for 5 minutes in isopropyl-alcohol, followed by UV ozone cleaning for 30 minutes. The cleaned glass substrate on which the transparent electrode line was formed was mounted on the substrate holder of the vacuum evaporation apparatus. HATCN (5 nm) was deposited as a hole injecting material on the side where the transparent electrode line was formed first. NPB (100 nm) was deposited thereon as a hole transporting material, and Compound 1 (10 nm) was deposited to prevent electrons from easily flowing into the hole transporting layer. Then, CBP: Ir (ppy) 3 was vapor-deposited at a mass ratio of 20: 1 to form a light emitting layer with a film thickness of 30 nm. After that, Alq3 (5 nm) and LiF (1 nm) were formed as an electron injecting material, and a negative electrode was formed with Al (80 nm).

device Example  15 to 18

An organic electroluminescent device of each of the device embodiments 15 to 18 was fabricated in the same manner as in the device example 14, except that the compound described in [Table 2] was used instead of the compound 1 described above.

device Comparative Example  2

The organic electroluminescent device for Comparative Example 2 was fabricated in the same manner as the devices of Examples 14 to 18, except that TCTA, which is generally used as an electron blocking layer instead of the compound prepared by the present invention, was used.

device Example  19 to 23

An organic electroluminescent device of each of the device embodiments 19 to 23 was fabricated in the same manner as in the device example 18 except that Ir (btp) 2 (acac) was used instead of the dopant Ir (ppy) 3.

device Comparative Example  3

The organic electroluminescent device for Comparative Example 3 was fabricated in the same manner as the devices of Examples 19 to 23, except that TCTA, which is generally used as an electron blocking layer instead of the compound prepared by the invention, was used.

The structure of the compound used above is as follows.

Hereinafter, the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 13 and the device comparison examples 1, 2, and 3 are compared, and the results are shown in [Table 1] and [Table 2] below.

[Table 1]

[Table 2]

Measurement of driving voltage and luminous efficiency

After fixing the organic electroluminescent device (substrate size: 25 × 25 mm 2 / deposition area: 2 × 2 mm 2) according to the above Examples and Comparative Examples to an IVL measurement set (CS-2000 + jig + IVL program) (Cd / m &lt; 2 &gt;), driving voltage (V) and luminous efficiency (cd / A) of the deposition surface were measured. The results are shown in Table 1 and Table 2, respectively.

From the results of the above Examples and Comparative Examples and [Table 1] and [Table 2], the device employing the organic luminescent compound represented by the formula (1) according to the present invention is a conventional blue luminescent material, The characteristics such as the driving voltage and the luminous efficiency are superior to those of the device employing the light emitting device and can be used effectively for display devices, display devices, lighting, and the like.

Claims (10)

An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]

In the above formula (1)
X is R ₁ -CR ₂ , wherein R ₁ and R ₂ are each independently selected from a substituted or unsubstituted alkyl group having 1 to 7 carbon atoms and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms,
A is represented by [Structural Formula 1] or [Structural Formula 2] below,
[Structural formula 1]

[Structural formula 2]

In the structural formula 1 or the structural formula 2,
L is a direct bond, a substituted or unsubstituted C6-C20 A substituted or unsubstituted arylene group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, n is an integer of 0 to 2, and when n is 2, A plurality of L's may be the same or different from each other,
Ar ₁ to Ar ₇ are the same or different and each represents a substituted or unsubstituted cycloalkyl group having 6 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms An aryl group,
Ar ₁ and Ar ₂ , Ar ₃ and Ar _4, and Ar ₅ and Ar ₆ may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the alicyclic or aromatic The carbon atom of the monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S and O,
p is an integer of 1 to 2, and when p is 2, a plurality of * - () may be the same or different from each other. The method according to claim 1,
R ₁ , R ₂ , L and Ar ₁ to Ar ₇ may be further substituted with one or more substituents, and the one or more substituents may be selected from the group consisting of hydrogen, deuterium, cyano, halogen, amino, , A halogenated alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, and an alkylsilyl group having 1 to 7 carbon atoms. The method according to claim 1,
The organic luminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds:

1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises an organic light emitting compound represented by Formula 1 according to Claim 1. 5. The method of claim 4,
Wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, a layer simultaneously transporting holes and holes, an electron transporting layer, an electron injecting layer, a layer that simultaneously transports electrons and electrons,
Wherein at least one of the layers comprises an organic light-emitting compound represented by the formula (1). 6. The method of claim 5,
Wherein the light emitting layer comprises an organic light emitting compound represented by the following formula (1). The method according to claim 6,
Wherein the organic light emitting compound represented by Formula 1 is used as a dopant compound in the light emitting layer. 8. The method of claim 7,
Wherein the light emitting layer further comprises at least one dopant compound other than the organic light emitting compound represented by Formula 1 and a host compound. 6. The method of claim 5,
Wherein the hole transport layer or the layer simultaneously injecting holes and transporting holes comprises an organic light emitting compound represented by the following formula (1). delete

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