KR101859372B1 - 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 the compound is employed as a hole transport compound in a dopant compound or a hole transport layer in a light emitting layer, An organic electroluminescent device having excellent light emission characteristics such as brightness and long life 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,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic light emitting compound used in an organic electroluminescent device and more specifically to an organic light emitting compound used as a hole transport compound in a hole transporting layer or a dopant compound in an organic electroluminescent device emitting layer, And an organic electroluminescent device in which luminous efficiency is remarkably improved.

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 luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently developed yet. 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.

US Pat. No. 7,053255 is disclosed as a blue light emitting material, but there is a problem that luminous efficiency and luminance are not sufficient. On the other hand, US Pat. No. 7233019 and Korean Patent Laid-Open Publication No. 2006-0006760 disclose an organic electroluminescent device using a substituted pyrene compound. However, since the color purity of blue is low, a deep blue It is difficult to realize a full-color full-color display.

The present invention relates to a novel organic electroluminescent compound which can be used as a hole transport compound in a light emitting layer or as a hole transporting compound in a hole transporting layer in an organic electroluminescent device, .

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 in the light emitting layer or the hole transporting layer can realize improved luminous efficiency and long life time characteristics, and the organic electroluminescent device employing the organic electroluminescent device 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 ₁ , X _2, and X ₃ are each independently CH or N.

L is a substituted or unsubstituted C3-C30 A substituted or unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, n is an integer of 0 to 3, and n is 2 or more , A plurality of Ls may be the same or different from each other.

Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are the same or different and each independently represents a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms which is unsubstituted or fused with one or more unsubstituted cycloalkyl having 3 to 30 carbon atoms and a substituted or unsubstituted substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms And a heteroaryl group having 2 to 50 carbon atoms.

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 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.

The 'substituted' in the 'substituted or unsubstituted' means that each of L, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be independently substituted with at least one substituent, One or more substituents are selected from the group consisting of hydrogen, deuterium, cyano, halogen, amino, nitro, hydroxyl, silyl, alkyl of 1 to 24 carbon atoms, halogenated alkyl of 1 to 24 carbon atoms, A substituted or unsubstituted aryl group having 3 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms substituted or unsubstituted, in which at least one of substituted or unsubstituted C3 to C30 cycloalkyl is fused, And a substituted or unsubstituted C 2 -C 50 heteroaryl group in which at least one unsubstituted C 3 -C 30 cycloalkyl is fused together.

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 formula 1 can be used for various organic layers of the organic electroluminescent device due to its structural specificity and is preferably used in a dopant compound or a hole transport compound .

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.

As described above, it is possible to synthesize an organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituent groups into the core structure according to Formula 1 of the present invention. 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 luminescent compound represented by the formula (1) of the present invention is characterized by introducing a substituent characteristic of the characteristic core structure and exhibiting excellent characteristics such as efficiency, driving voltage and lifetime in the light emitting layer and the hole transporting layer of the organic electroluminescent device It is possible to realize an organic electroluminescent device.

The organic luminescent compound represented by Formula 1 according to the present invention can be applied to an element 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  One : Intermediate 1 Synthesis of -1

3-bromo-9H-carbazole (5.4 g, 0.022 mol), Pd (dba) ₂ (0.5 g, 0.0005 mol) and sodium tert-butoxide (1.9 g, 0.020 mol) was added 100 mL of toluene, and the mixture was reacted at 95 DEG 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 3.5 g (yield 62%) of Intermediate 1-1. (m / z = 566)

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

To a solution of bis (pinacolato) dibron (3.0 g, 0.012 mol) PdCl ₂ (dppf) (0.4 g, 0.0005 mol) and potassium acetate (2.8 g, 0.020 mol) in Intermediate 1-1 (5.7 g, 0.010 mol) 4-dioxane (120 mL), and the mixture was reacted for 24 hours at 95 ° C. After completion of the reaction, the reaction mixture was cooled, and the product was separated into H ₂ O: MC and purified by column chromatography (n-hexane: MC) Yield: 71%). (m / z = 660)

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to diphenylamine (1.7 g, 0.010 mol) in the same manner as in Example 1- g (yield: 61%). (m / z = 229)

(4) Manufacturing example  4: Synthesis of compound 1

Boronic acid (4.6 g, 0.020 mol), Pd (PPh ₃ ) ₄ (0.6 g, 0.0005 mol) and potassium carbonate (2.8 g, 0.020 mol) were added to Intermediate 1-2 (7.9 g, 0.012 mol) 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 5.8 g (yield 73%) of <Compound 1>. (m / z = 220)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m, 7.30 / s) 2H (8.55 / d, 8.34 / s, 7.94 / d, 7.50 / d, 7.33 / m, 7.25 / m, 6.78 / s, 6.10 / s) 4H (7.58 d, 6.81 m) 8H (7.20 m, 6.29 / d)

LC / MS: m / z = 795 [(M + 1) ^&lt; ^{+ &}

Example  2: Synthesis of Compound 2

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to dip-tolylamine (2.0 g, 0.010 mol) in the same manner as in Example 1- > 1.5 g (yield: 58%). (m / z = 257)

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

The intermediate 1-3 (2.3 g, 0.010 mol) was added to Intermediate 1-2 (7.9 g, 0.012 mol) and the compound was synthesized in the same manner as in Example 1- (4) 51%). (m / z = 727)

(3) Manufacturing example  3: Synthesis of Compound 2

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 2-1 (2.6 g, 0.010 mol) was added to Intermediate 2-2 (8.7 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m, 7.30 / s) 2H (8.55 / d, 8.34 / s, 7.94 / d, 7.50 / d, 7.33 / m, 7.25 / m, 6.81 d, 6.21 / d, 2.34 / s) 4H (7.58 / d, 7.20 /

LC / MS: m / z = 824 [(M + 1) ^&lt; ^{+ &}

Example  3: Synthesis of Compound 3

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

<Intermediate 3-1> 2.0 (4-bromophenyl) trimethylsilane (2.5 g, 0.011 mol) was added to 3,5-dimethylaniline (1.2 g, 0.010 mol) g (yield: 76%). (m / z = 269)

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 3-1 (2.7 g, 0.010 mol) in the same manner as in Example 1- > 1.9 g (yield: 58%). (m / z = 329)

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

(1.7 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- 58%). (m / z = 295)

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 3-3 (3.0 g, 0.010 mol) to obtain Intermediate 3-4 > 1.9 g (yield: 53%). (m / z = 355)

(5) Manufacturing example  5: Synthesis of intermediate 3-5

Intermediate 3-2 (3.3 g, 0.010 mol) was added to Intermediate 1-2 (7.9 g, 0.012 mol) and the compound was synthesized in the same manner as in Example 1- (4) 51%). (m / z = 827)

(6) Manufacturing example  6: Synthesis of Compound 3

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 3-1 (3.6 g, 0.010 mol) was added to Intermediate 3-5 (9.9 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m, 7.30 / s) 2H (8.55 / d, 8.34 / s, 8.07 / s, 8.02 / d, 7.94 / d, 7.54 / m, 7.53 7.58 / d, 7.52 / d, 7.51 / m, 7.20 / m, 6.29 / d)

LC / MS: m / z = 1022 [(M + 1) ^&lt; ^{+ &}

Example  4: Synthesis of compound 4

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

(Intermediate 4-1) was synthesized in the same manner as in Example 1 (4) except that phenylboronic acid (1.4 g, 0.012 mol) was added to 3-bromonaphthalen-1-ol (2.2 g, 0.010 mol) 1.6 g (yield: 73%) was obtained. (m / z = 220)

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

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 (yield: 70%) of Intermediate 4-2 (m / z = 352)

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

2.2 g (yield: 74%) of Intermediate 4-3 was synthesized in the same manner as in PREPARATION 1 (PREPARATION 1), except that aniline (1.0 g, 0.011 mol) was added to Intermediate 4-2 (3.5 g, &Lt; / RTI > (m / z = 295)

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 4-3 (3.0 g, 0.010 mol) to obtain Intermediate 4-4 > 1.8 g (yield 52%). (m / z = 355)

(5) Manufacturing example  5: Synthesis of Compound 4

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 1-2 (6.6 g, 0.010 mol) was added to Intermediate 4-4 (7.1 g, 0.020 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.49 / d, 8.07 / d, 7.78 / d, 7.54 / m, 7.53 / m, 7.45 / m, 7.41 / m, 7.30 / s, 6.81 / m 7.71 / d, 7.51 / m, 7.50 / d, 7.33 / m, 7.25 / m, 7.20 / m, 7.15 / d, 6.78 / s , 6.61 d, 6.36 s, 6.29 d, 6.10 d, 2.34 s) 3H (0.25 s) 4H (7.58 d)

LC / MS: m / z = 1048 [(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 (1) except that 4-bromodibenzo [b, d] thiophene (2.9 g, 0.011 mol) 1.9 g (yield 67%) was obtained. (m / z = 289)

(2) Manufacturing example  2: Synthesis of Intermediate 5-2

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 5-1 (2.9 g, 0.010 mol) in the same manner as in Example 1- > 1.8 g (yield 52%). (m / z = 349)

(3) Manufacturing example  3: Synthesis of Compound 5

6.3 g (yield: 61%) of Compound 5 was synthesized in the same manner as in Example 1- (4), except that Intermediate 1-2 (7.9 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (745 / m, 7.30 / s) 2H (8.55 / d, 8.45 / d, 8.34 / s, 7.98 / d, 7.94 / d, 7.81 / d, 7.52 7.58 / d, 6.98 / d, 6.57 / m, 7.50 / d, 7.50 / d, 7.33 / m, 7.27 / m, 7.25 / m, 6.86 / d, 6.78 / / d)

LC / MS: m / z = 1036 [(M + 1) ^&lt; ^{+ &}

Example  6: Synthesis of Compound 6

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

Intermediate 6-1> 1.5 (4-bromonaphthalen-2-ol) was synthesized in the same manner as in Example 1 (4) except that phenyl boronic acid (1.5 g, 0.012 mol) g (yield: 68%). (m / z = 220)

(2) Manufacturing example  2: Synthesis of intermediate 6-2

2.4 g (yield: 68%) of Intermediate 6-2 was synthesized in the same manner as in Example 4 (2) except that trifluoromethane sulfonic anhydride (3.1 g, 0.011 mol) was used in Intermediate 6-1 (2.2 g, 0.010 mol) &Lt; / RTI > (m / z = 352)

(3) Manufacturing example  3: Synthesis of intermediate 6-3

1.7 g (Yield: 59%) of Intermediate 6-3 was synthesized in the same manner as in PREPARATION 1 (PREPARATION 1), except that aniline (1.0 g, 0.011 mol) was added to Intermediate 6-2 (3.5 g, 0.010 mol) &Lt; / RTI > (m / z = 295)

(4) Manufacturing example  4: Synthesis of intermediate 6-4

was synthesized in the same manner as in PREPARATION 1-PREPARATION EXAMPLE (1), and 1.6 g (yield: 66%) of Intermediate 6-4 was obtained by introducing (4-bromophenyl) trimethylsilane (2.5 g, 0.011 mol) %). (m / z = 241)

(5) Manufacturing example  5: Synthesis of intermediate 6-5

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 6-4 (2.4 g, 0.010 mol) to obtain Intermediate 6-5 > 1.7 g (yield: 57%). (m / z = 301)

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 6-3 (3.0 g, 0.010 mol) to obtain Intermediate 6-6 > 2.3 g (yield 66%). (m / z = 355)

(7) Manufacturing example  7: Synthesis of intermediate 6-7

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 1-2 (7.9 g, 0.012 mol) was added to Intermediate 6-1 (3.6 g, 0.010 mol) 59%). (m / z = 853)

(8) Manufacturing example  8: Synthesis of Compound 6

6.3 g (yield: 63%) of Compound 6 was synthesized in the same manner as in Example 1- (4) except that Intermediate 6-5 (3.0 g, 0.010 mol) was added to Intermediate 6-7 (10.2 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.43 / d, 7.85 / d, 7.46 / m, 7.45 / m, 7.41 / m, 7.32 / m, 7.30 / s, 6.99 / s, 6.76 / s 7.55 / d, 7.15 / d, 6.81 / m, 6.78 / s, 6.61 / d , 6.10 / s) 3H (0.25 / s) 4H (7.58 / d, 7.20 /

LC / MS: m / z = 994 [(M + 1) ^&lt; ^{+ &}

Example  7: Synthesis of Compound 7

(One) Manufacturing example  1: Synthesis of Intermediate 7-1

Synthesis was conducted in the same manner as in Example 1 (1) except that 3-bromo-9H-carbazole (5.4 g, 0.022 mol) was added to 2,6-diiodopyridine (3.3 g, 0.010 mol) > 2.8 g (yield 50%). (m / z = 567)

(2) Manufacturing example  2: Synthesis of intermediate 7-2

Synthesis was conducted in the same manner as in Example 1 (2), except that bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to Intermediate 7-1 (5.7 g, 0.010 mol) Yield: 66%). (m / z = 661)

(3) Manufacturing example  3: Synthesis of intermediate 7-3

4-tert-butylbenzene (2.3 g, 0.011 mol) was added to 1-bromo-4-amine (1.7 g, 0.010 mol) -3> were obtained in an amount of 2.0 g (yield 66%). (m / z = 301)

(4) Manufacturing example  4: Synthesis of Intermediate 7-4

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 7-3 (3.0 g, 0.010 mol), and <Intermediate 7- 4> 2.4 g (yield 66%). (m / z = 361)

(5) Manufacturing example  5: Synthesis of Compound 7

Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 7-4 (7.2 g, 0.020 mol) was added to Intermediate 7-2 (7.9 g, 0.012 mol) %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.66 / m) 2H (8.55 / d, 8.34 / s, 7.94 / d, 7.90 / d, 7.33 / m, 7.25 / m, 6.78 / s, 6.10 7.55 / d) 6H (1.35 / s) 4H (7.58 d, 7.54 d, 7.52 d, 7.51 dm, 7.01 d, 6.69 d, 6.55 d)

LC / MS: m / z = 1061 [(M + 1) ^&lt; ^{+ &}

Example  8: Synthesis of Compound 8

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

biphenyl-4-amine (1.9 g, 0.011 mol) was added 4-bromodibenzo [b, d] thiophene (2.6 g, 0.010 mol) 1 &gt; 2.0 g (yield: 58%). (m / z = 351)

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 8-1 (3.5 g, 0.010 mol)

Synthesis was conducted in the same manner as in Example 1 to obtain 2.5 g (yield: 62%) of Intermediate 8-2. (m / z = 411)

(3) Manufacturing example  3: Synthesis of Compound 8

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 7-2 (7.9 g, 0.012 mol) was added to Intermediate 8-2 (8.2 g, 0.020 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.66 / m) 2H (8.55 / d, 8.45 / d, 8.34 / s, 7.98 / d, 7.94 / d, 7.90 / d, 7.81 / d, 7.52 7.58 / d, 7.51 / m, 6.69 / m, 7.50 / m, 7.41 / m, 7.33 / m, 7.27 / d, 7.25 / / d)

LC / MS: m / z = 1161 [(M + 1) ^&lt; ^{+ &}

Example  9: Synthesis of Compound 9

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

Synthesis was conducted in the same manner as in Example 1 (1) except that 4-bromodibenzo [b, d] thiophene (2.9 g, 0.011 mol) was added to aniline (0.9 g, 0.010 mol) g (yield: 64%). (m / z = 275)

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 9-1 (2.8 g, 0.010 mol) in the same manner as in Example 1- > 2.1 g (yield 62%). (m / z = 335)

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

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 7-2 (7.9 g, 0.012 mol) was added to Intermediate 9-2 (3.4 g, 0.010 mol) 51%). (m / z = 834)

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

was synthesized in the same manner as in Example 1 (1) except that 1-bromo-4-tert-butylbenzene (2.3 g, 0.011 mol) was added to aniline (0.9 g, 0.010 mol) (Yield: 71%). (m / z = 225)

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

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 9-4 (2.3 g, 0.010 mol) to obtain Intermediate 9-5 > 1.7 g (yield 59%). (m / z = 285)

(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 (2.9 g, 0.010 mol) was added to Intermediate 9-3 (10.0 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 7.98 / d, 7.81 / d, 7.66 / m, 7.52 / m, 7.50 / m) 2H (8.55 / d, 8.34 / s, 7.94 d, 7.20 / d, 7.90 / d, 7.33 / m, 7.25 / m, 7.01 / d, 6.81 / m, 6.78 / s, 6.55 / d, (1.35 / s)

LC / MS: m / z = 959 [(M + 1) ^&lt; ^{+ &}

Example  10: Synthesis of Compound 10

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

Intermediate 2-1 (2.6 g, 0.010 mol) was added to Intermediate 7-2 (7.9 g, 0.012 mol) and the compound was synthesized in the same manner as in Example 1- (4) 54%). (m / z = 756)

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

Synthesis was conducted in the same manner as in Example 1 (1) except that 4-bromodibenzo [b, d] furan (2.7 g, 0.011 mol) was added to p-toluidine (1.1 g, 0.010 mol) 1.9 g (yield 70%) was obtained. (m / z = 273)

(3) Manufacturing example  3: Synthesis of intermediate 10-3

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 10-2 (2.7 g, 0.010 mol) in the same manner as in Example 1- > 2.3 g (yield 68%). (m / z = 333)

(4) Manufacturing example  4: Synthesis of Compound 10

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 10-1 (9.1 g, 0.012 mol) was added to Intermediate 10-3 (3.3 g, 0.010 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.89 / d, 7.66 / d, 7.66 / m, 7.38 / m, 7.32 / m, 7.25 / d, 7.07 / m, 6.39 / d) 2H (8.55 d), 6.98 (d), 6.51 (d, 8.34 / s, 7.94 / d, 7.90 / d, 7.33 / / d)

LC / MS: m / z = 929 [(M + 1) ^&lt; ^{+ &}

Example  11: Synthesis of Compound 11

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

Synthesis was conducted in the same manner as in Example 1 (1) except that 1-bromo-9,9-dimethyl-9H-fluorene (3.0 g, 0.011 mol) was added to aniline (0.9 g, 0.010 mol) -1> 1.7 g (yield: 61%). (m / z = 285)

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

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (1), except that (E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 11-1 (2.9 g, 0.010 mol) > 2.0 g (yield: 58%). (m / z = 345)

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

Intermediate 7-2 (7.9 g, 0.012 mol) was added to Intermediate 11-2 (3.5 g, 0.010 mol) and synthesized in the same manner as Example 1-Preparation Example (4) 51%). (m / z = 844)

(4) Manufacturing example  4: Synthesis of Compound 11

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 3-4 (3.6 g, 0.010 mol) was added to Intermediate 11-3 (10.1 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.49 / d, 8.07 / d, 7.87 / d, 7.78 / d, 7.66 / m, 7.55 / d, 7.54 / m, 7.53 / m, 7.38 / m D, 7.90 / d, 7.79 / d, 7.51 / m, 7.33 / m, 7.25 / , 6.81 / m, 6.78 / s, 6.10 / s, 1.72 / s) 4H (7.58 / d, 7.20 /

LC / MS: m / z = 1039 [(M + 1) ^&lt; ^{+ &}

Example  12: Synthesis of Compound 12

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

Synthesis was conducted in the same manner as in Example 1 (1) except that 3-bromo-9H-carbazole (5.4 g, 0.022 mol) was added to 1,4-diiodobenzene (2.4 g, 0.010 mol) 3.5 g (yield 62%) was obtained. (m / z = 566)

(2) Manufacturing example  2: Synthesis of intermediate 12-2

Intermediate 12-2 (3.6 g, 0.012 mol) was synthesized by the same method as in Example 1 (1) except that bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to Intermediate 12-1 (Yield: 55%). (m / z = 660)

(3) Manufacturing example  3: Synthesis of intermediate 12-3

Synthesis was conducted in the same manner as in Example 1 (1) except that 1-bromo-3,5-dimethylbenzene (2.1 g, 0.011 mol) was added to 3,5-dimethylaniline (1.2 g, 0.010 mol) 3> 1.5 g (yield 65%). (m / z = 225)

(4) Manufacturing example  4: Synthesis of intermediate 12-4

(E) -1,2-dichloroethene (1.1 g, 0.011 mol) was added to Intermediate 12-3 (2.3 g, 0.010 mol) to obtain Intermediate 12- 4> 1.7 g (yield: 61%). (m / z = 285)

(5) Manufacturing example  5: Synthesis of intermediate 12-5

Intermediate 12-4 (2.9 g, 0.010 mol) was added to Intermediate 12-2 (7.9 g, 0.012 mol) and the compound was synthesized in the same manner as in Example 1- (4) 55%). (m / z = 783)

(6) Manufacturing example  6: Synthesis of Compound 12

4.5 g (yield: 53%) of compound 12 was synthesized in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 12 (9.3 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.55 / d, 8.34 / s, 7.94 / d, 7.33 / m, 7.25 / m, 6.81 / m, 6.78 / s, 6.10 / s) 4H (7.62 d, 7.58 / d, 7.20 / m, 7.15 / d, 6.61 / d, 6.29 / d)

LC / MS: m / z = 852 [(M + 1) ^&lt; ^{+ &}

Example  13: Synthesis of compound 13

(One) Manufacturing example  1: Synthesis of compound 13

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 6-5 (6.0 g, 0.020 mol) was added to Intermediate 12-2 (7.9 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.55 / d, 8.34 / s, 7.94 / d, 7.33 / m, 7.25 / m, 6.81 / m, 6.78 / s, 6.71 / s, 6.10 / s ) 4H (7.62 / d, 7.58 / d, 7.20 / m, 6.36 / s, 6.29 / d, 2.34 / s)

LC / MS: m / z = 940 [(M + 1) ^&lt; ^{+ &}

Example  14: Synthesis of compound 14

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

Malonic acid (1.1 g, 0.011 mol), piperidine (0.10 mL) and pyridine (6 mL) were added to 4-iodobenzaldehyde (2.3 g, 0.010 mol) and reacted with heating under reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled to 0 ° C and acidified with 6 N hydrochloric acid. After filtration and drying, 2.3 g (yield: 85%) of Intermediate 14-1 was obtained. (M / z = 274)

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

Intermediate 14-1 (2.4 g, 0.010 mol) was distilled in acetonitrile and 48% HBr was added. NaNO ₂ was added and reacted. After completion of the reaction, CH ₃ Cl ₃ is added. After the reaction mixture was separated into layers, Na ₂ SO ₄ was added and concentrated in vacuo. After completion of the reaction, column purification (HEXANE: EA) yielded 2.8 g (yield 92%) of Intermediate 14-2. (m / z = 308)

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

Synthesis was conducted in the same manner as in Example 1 (1) except that Intermediate 14-2 (3.4 g, 0.0211 mol) was added to 4-methyl-N-phenylaniline (1.8 g, 0.010 mol) g (yield: 51%). (m / z = 364)

(4) Manufacturing example  4: Synthesis of Compound 14

Synthesis was conducted in the same manner as in Example 1 (1) except that Intermediate 12-2 (7.9 g, 0.012 mol) was added to Intermediate 14-3 (3.6 g, 0.010 mol) %).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.55 / d, 8.46 / d, 7.94 / d, 7.70 / d, 7.63 / d, 7.33 / m, 7.25 / m, 6.95 / s) 4H (7.77 / d, 7.62 / d, 6.63 / d) 8H (7.15 / d, 6.61 / d) 12H (0.25 / s)

LC / MS: m / z = 976 [(M + 1) ^&lt; ^{+ &}

Example  15: Synthesis of compound 15

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

Synthesis was carried out in the same manner as in PREPARATION 1-PREPARATION (1), except that Intermediate 14-2 (3.4 g, 0.011 mol) was added to bis (4- (trimethylsilyl) phenyl) amine (3.1 g, 0.010 mol) 1> 3.2 g (yield 65%). (m / z &lt; / RTI &gt; = 494)

(2) Manufacturing example  2: Synthesis of compound 15

Synthesis was conducted in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 12-2 (7.9 g, 0.012 mol) was added to Intermediate 15-1 (9.8 g, 0.020 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 2H (8.55 / d, 8.46 / s, 7.94 / d, 7.70 / d, 7.63 / d, 7.33 / m, 7.25 / m, 6.81 / m, 2.34 / s ) 4H (7.77 d, 7.62 d, 7.20 m, 6.98 d, 6.95 s, 6.51 d) 8H (6.63 d)

LC / MS: m / z = 1236 [(M + 1) ^&lt; ^{+ &}

Example  16: Synthesis of Compound 16

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

The intermediate 14-2 (3.4 g, 0.011 mol) was added to N- (biphenyl-4-yl) -9,9-dimethyl-9H- fluoren- (Yield: 68%) was obtained by the same method as in (1). (m / z = 542)

(2) Manufacturing example  2: Synthesis of Compound 16

8.1 g (Yield: 61%) of Compound 16 was synthesized in the same manner as in PREPARATION 1 (PREPARATION 4), except that Intermediate 1-2 (7.9 g, 0.012 mol) was added to Intermediate 16-1 (10.8 g, ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.45 / m, 7.30 / d) 2H (8.55 / d, 8.46 / s, 7.94 / d, 7.87 / d, 7.70 / d, 7.63 / d, 7.62 7.55 / d, 7.50 / d, 7.41 / m, 7.38 / m, 7.33 / m, 7.28 / / s, 6.69 / d, 6.63 / d, 1.72 / s)

LC / MS: m / z = 1332 [(M + 1) ^&lt; ^{+ &}

Example  17: Synthesis of Compound 17

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

1.6 g (0.011 mol) of 4-bromodibenzo [b, d] furan was added to aniline (0.9 g, 0.010 mol) in the same manner as in Example 1- (Yield: 63%). (m / z < / RTI > = 259)

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

Intermediate 14-2 (3.4 g, 0.011 mol) was added to Intermediate 17-1 (2.6 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 1- 54%). (m / z = 440)

(3) Manufacturing example  3: Synthesis of intermediate 17-3

(Intermediate 17-3) (4.3 g, yield) in the same manner as in Example 1 (4) except that Intermediate 1-2 (2.2 g, 0.011 mol) 48%). (m / z < / RTI > = 894)

(4) Manufacturing example  4: Synthesis of intermediate 17-4

Intermediate 14-2 (3.4 g, 0.011 mol) was added to Intermediate 9-1 (2.8 g, 0.010 mol) and the same procedure as described in Preparation Example (1) Yield: 54%). (m / z = 456)

(5) Manufacturing example  5: Synthesis of Compound 17

7.6 g (Yield: 66%) of compound 17 was synthesized in the same manner as in PREPARATION 1-PREPARATION (4), except that Intermediate 17-4 (4.6 g, 0.010 mol) was added to Intermediate 17-3 (10.8 g, 0.012 mol) ).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.41 / d, 7.98 / d, 7.89 / d, 7.81 / d, 7.66 / d, 7.66 / m, 7.52 / m, 7.50 / m, 7.38 / m D, 8.46 / s, 7.94 / d, 7.90 / d, 6.81 / m, 7.70 / d, 7.32 / m, 7.27 / m, 7.25 / d, 7.07 / , 7.63 / d, 7.33 / m, 7.25 / m) 4H (7.77 / d, 7.20 /

LC / MS: m / z = 1145 [(M + 1) ^&lt; ^{+ &}

device Example  1: Compound 1 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, followed by deposition of <Compound A>: <Compound 1> 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  2 to 17

An organic electroluminescent device of each of the device embodiments 2 to 17 was fabricated in the same manner as in the device example 1, except that the compound described in [Table 1] was used in place of the compound 2 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  18: 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  19 to 25

An organic electroluminescent device of each of the device examples 19 to 25 was fabricated in the same manner as in the device example 18, 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 19 to 25, except that TCTA, which is generally used as an electron blocking layer instead of the compound prepared by the invention, was used.

device Example  26 to 33

An organic electroluminescent device of each of the device embodiments 26 to 33 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 26 to 33, 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.

The results of comparing the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 33 and the device comparison examples 1, 2, and 3 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 examples and the 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], it can be seen that the organic luminescent compound of Formula 1 according to the present invention has a driving voltage And luminescence efficiency, it can be used 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 ₁ , X ₂ and X ₃ are each independently CH or N,
L is a direct bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; n is an integer of 0 to 3; when n is 2 or more, a plurality of L's are the same or different,
Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms ,
The 'substituted' in the 'substituted or unsubstituted' means that the above-mentioned L, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ each independently can be substituted with at least one substituent, A halogen group, an amino group, a nitro group, a hydroxyl group, a silyl group, an alkyl group having 1 to 7 carbon atoms, a halogenated alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 20 carbon atoms and an aryl group having 3 to 30 carbon atoms Lt; / RTI &gt; delete 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] to [500]:

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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