KR101809897B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

[구조식 1]

[구조식 2]

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound used in an organic electroluminescent device and is characterized by having at least one substituent represented by the following formula 1 and represented by the following formula 1 or formula 2, When employed as a host compound or a dopant compound in a light emitting layer, an organic electroluminescent device having excellent light emitting properties such as a driving voltage, a luminance and a long life can be realized.
[Chemical Formula 1]

[Structural formula 1]

[Structural formula 2]

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, and more particularly, to an organic light emitting compound that is employed as a host compound or a dopant compound in a light emitting layer of an organic electroluminescent device and an organic electroluminescent device .

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 the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and 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.

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. 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 provides a novel organic electroluminescent compound which can be used as a host compound or a dopant compound in a light emitting layer of an organic electroluminescent device to realize excellent luminescent characteristics and an organic electroluminescent device including the same.

In order to solve the above problems, the present invention provides an organic electroluminescent compound having at least one substituent of the following structural formula 1 or structural formula 2 in a core skeleton represented by the following formula 1: An electroluminescent device is provided.

[Chemical Formula 1]

[Structural formula 1]

[Structural formula 2]

The specific structures and substituents of the organic luminescent compounds according to the above formulas (1) and (1) to (2) will be described later.

The organic electroluminescent device employing the organic electroluminescent compound according to the present invention in the electroluminescent layer can realize a further improved luminous efficiency and long life, and the organic electroluminescent device employing the same 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)

R ₁ to R ₁₄ are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 aryl A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 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, a substituted or unsubstituted, substituted or unsubstituted aryl group having 5 to 50 carbon atoms in which one or more substituted or unsubstituted C3 to C30 cycloalkyl is fused, A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted silyl group, an amino group, a thiol group, a cyano group, a hydroxyl group, a nitro group and a halogen group, each of which is substituted by one or more fused cycloalkyl having 3 to 30 carbon atoms It is selected from the group.

Each of R ₁ to R ₁₄ may be further substituted with one or more substituents. The substituent may be substituted with at least one substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, An alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, 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, 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, and an aryloxy group having 1 to 24 carbon atoms.

R ₁ to R ₁₄ may be bonded to each other or may be connected with 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 >

The organic luminescent compound represented by Formula 1 according to the present invention is characterized in that at least one of R ₁ to R ₁₄ corresponding to the substituent of the core skeleton represented by Formula 1 is the following Formula 1 do.

[Structural formula 1]

In the structural formula 1,

L ₁ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon 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 ₁ and Ar ₂ 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, hwandoen is selected from a heteroaryl group having a carbon number of 3 to 30 cycloalkyl are fused one or more substituted or unsubstituted C2 to 50, wherein Ar ₁ and Ar ₂ are coupled or connected with the adjacent substituents to each other cycloaliphatic, aromatic And the carbon atom of the single alicyclic or aromatic cyclic ring or the polycyclic ring may be any one selected from N, S and O Or more hetero atoms which may be substituted.

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.

Further, L _1, Ar ₁ and Ar ₂ each may be further substituted with one or more substituents, the one or more substituents are deuterium, a cyano group, an alkyl group, a halogen group, a hydroxyl group, a nitro group, having 1 to 24 carbon atoms, A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 24 carbon atoms, 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, and an aryloxy group having 1 to 24 carbon atoms.

The organic electroluminescent compound represented by Formula 1 according to the present invention is characterized in that at least one of R ₁ to R ₁₄ corresponding to the substituent of the core skeleton represented by Formula 1 is represented by Formula 2 do.

[Structural formula 2]

In the above formula 2,

L ₂ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylene 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, Substituted or unsubstituted heteroarylene groups having 2 to 50 carbon atoms in which at least one unsubstituted fused at least one of arylene groups having 5 to 50 carbon atoms and substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms is fused and m is 0 to 4 And when m is 2 or more, a plurality of L ₂ may be the same or different from each other.

And Ar ₃ 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 aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, And a substituted or unsubstituted C2 to C50 heteroaryl group in which at least one of 3 to 30 cycloalkyls is fused.

q is an integer of 0 to 3, and when q is 2 or more, a plurality of Ar ₃ may be the same or different.

The plurality of Ar ₃ and substituents thereof may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be N, S, and O ≪ / RTI >

Each of L ₂ and Ar ₃ may be further substituted with one or more substituents. The substituent may be one or more substituents selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, 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, 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, and an aryloxy group having 1 to 24 carbon atoms.

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 or unsubstituted" means a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, alkyl, cycloalkyl, , An arylsulfoxy group, an alkenyl group, a silyl group, a boron group, an alkylamine group, an aralkylamine group, an arylamine group, an aryl group, a fluorenyl group, a carbazole group and at least one of N, O and S atoms Substituted or unsubstituted with at least one substituent in the heterocyclic group.

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 Formula 1 can be used in various organic layers of organic electroluminescent devices due to its structural specificity, and can be preferably used as a host compound or a dopant compound in a light emitting layer.

Specific examples of the organic luminescent compound that may be employed as the host compound or the dopant compound of the light emitting layer 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 layers may include a compound represented by the formula 1. Preferably, the organic luminescent compound according to the present invention is a host or a dopant substance in the luminescent layer .

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

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 1-bromoanthracene (2.6 g, 0.010 mol) 4-dioxane (100 mL), and the mixture was reacted at 95 ° C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H ₂ O: MC and column-purified (n-hexane: MC) to obtain 2.2 g (yield 71%) of Intermediate 1-1. (m / z = 304)

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

Pd (PPh ₃ ) ₄ (0.6 g, 0.0005 mol) and potassium carbonate (2.8 g, 0.020 mol) were added to Intermediate 1-1 (3.6 g, 0.012 mol) with 3-bromo-2-iodophenol 100 mL of THF was added, and the mixture was reacted at 65 DEG C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 2.5 g (yield: 73%

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

IPy ₂ BF ₄ (7.5 g, 0.020 mol) was dissolved in dichloromethane and then cooled to -78 ° C. HBF ₄ (6.5 g, 0.040 mol) was added thereto, followed by stirring for 10 minutes. After filtration of the solid, the filtrate was cooled to -60 DEG C, and intermediate 1-2 (3.5 g, 0.010 mol) was slowly dropped. 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 2.2 g (m / z = 359)

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

Compound 1-3 (3.6 g, 0.010 mol) was dissolved in 100 mL of diethyl ether, and AlCl ₃ (1.6 g, 0.012 mol) was slowly dropped. Stir for 15 min and then cool to 0 < 0 > C. After stirring for 1 hour, when the reaction was completed, slowly cooled to room temperature, and EA was added slowly until no bubbling occurred. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 2.9 g (yield: 85%

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

Intermediate 1-4 (3.5 g, 0.010 mol) was dissolved in 50 mL of DMSO, and sodium tert-butoxide (4.8 g, 0.050 mol) was added thereto at room temperature. Then, methyl iodide (7.3 g, 0.050 mol) was slowly dropped and stirred for 1 hour. After completion of the reaction, the reaction mixture was cooled, and subjected to column separation on H ₂ O: MC, followed by column purification (n-hexane: MC) to obtain 2.2 g (m / z = 373)

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

70 mL of TOL was added to bromoethene (1.4 g, 0.013 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 separated into H ₂ O: MC and purified by column chromatography (n-HEXANE: MC) to obtain 1.6 g (51%) of Intermediate 1-6 (m / z = 318)

(7) Manufacturing example  7: Synthesis of intermediate 1-7

50 mL of DMF was added to N-bromosuccinimide (1.8 g, 0.010 mol) in Intermediate 1-6 (3.2 g, 0.010 mol), and the mixture was reacted at 20 ° C for 8 hours with stirring. After completion of the reaction H ₂ 0: After phase separation with ethyl acetate and column purification: yield (n-Hexane MC) and 1.9 g (48%) of <Intermediate 1-7> (m / z = 397 ).

(8) Manufacturing example  8: Synthesis of intermediate 1-8

(Intermediate 1-8) was obtained in the same manner as in Example 1 (1), except that Intermediate 1-7 (4.0 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, 0.012 mol) Yield: 73%). (m / z = 444)

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

Intermediate 1-9 was synthesized by the same method as in Example 1 (2) except that phenyl boronic acid (1.4 g, 0.012 mol) was added to 4-bromonaphthalen-1-ol (2.2 g, 0.010 mol) 1.6 g (yield: 73%). (M / z = 220)

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

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, separated into H ₂ O: MC and subjected to column purification (n-hexane: MC) to obtain 2.5 g (m / z = 352)

(11) Manufacturing example  11: Synthesis of compound 1

Synthesis was conducted in the same manner as in Example 1-Preparation Example (2), except that Intermediate 1-10 (3.5 g, 0.010 mol) was added to Intermediate 1-8 (5.3 g, 0.012 mol) 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.12 / d, 8.08 / d, 7.94 / d, 7.92 / d, 7.85 / s, 7.82 / d, 7.75 / m, 7.75 / d 7.91 / d, 7.79 / d, 7.51 / m, 7.39 / m, 1.98 / s)

LC / MS: m / z = 521 [(M + 1) ^&lt; ^{+ &}

Example  2: Synthesis of Compound 2

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

<Intermediate 2-1> was obtained in the same manner as in Example 1 (1) except that 1,4-dibromoanthracene (3.4 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, 0.012 mol) (Yield: 73%). (m / z = 383)

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

Intermediate 2-2 (4.0 g, 0.010 mol) was reacted with 3-bromo-2-iodophenol (3.0 g, 0.010 mol) > 2.7 g (yield 62%). (M / z = 429)

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

Intermediate 2-2 (4.3 g, 0.010 mol) was added and 2.3 g (52% yield) of Intermediate 2-3 was obtained by the same method as in Example 1- (3) = 439)

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

Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 2-3 (4.4 g, 0.010 mol) was added to obtain 3.2 g (yield 76%) of Intermediate 2-4 (m / z = 424)

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

Synthesis was conducted in the same manner as in Example 1 (5), except that Intermediate 2-4 (4.2 g, 0.010 mol) was added to obtain 2.8 g (yield: 61%) of Intermediate 2-5 (m / z = 452)

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

2.1 g (yield: 53%) of Intermediate 2-6 was synthesized in the same manner as in Example 1- (6) except that bromoethene (1.4 g, 0.013 mol) was added to Intermediate 4-5 (4.2 g, 0.010 mol) %). (M / z = 397)

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

3.2 g (0.07 mol) of Intermediate 2-7 was obtained in the same manner as in Example 1 (1) except that Intermediate 2-6 (4.0 g, 0.010 mol) and bis (pinacolato) dibron Yield: 73%). (m / z = 444)

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

2-ylboronic acid (2.1 g, 0.012 mol) was added to 1,4-dibromobenzene (2.4 g, 0.010 mol) and the intermediate <2-8 > 1.6 g (yield: 71%). (M / z = 283)

(9) Manufacturing example  9: Synthesis of Compound 2

Intermediate 2-8 (2.3 g, 0.008 mol) was added to Intermediate 2-7 (4.4 g, 0.010 mol) and the compound was synthesized in the same manner as in Example 1- (2) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.13 / s, 8.12 / d, 7.94 / d, 7.92 / d, 7.82 / d, 7.75 / d, 7.73 / d, 7.61 / s, 7.58 / d , 7.55 / m) 2H (8.00 d, 7.91 d, 7.59 m, 7.39 m, 1.98 s)

LC / MS: m / z = 521 [(M + 1) ^&lt; ^{+ &}

Example  3: Synthesis of Compound 3

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

<Intermediate 3-1> was obtained in the same manner as in Example 1 (1), except that 1,3-dibromoanthracene (3.4 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, 0.012 mol) (Yield: 73%). (m / z = 383)

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

Intermediate 3-2 (3.8 g, 0.010 mol) was synthesized in the same manner as in Example 1 (2) except that 3-bromo-2-iodophenol (3.0 g, 0.010 mol) > 2.5 g (yield: 58%). (M / z = 428)

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

2.2 g (yield: 51%) of Intermediate 4-2 (m / z) was obtained by the same method as in Example 1- (3) except that Intermediate 3-2 (4.3 g, 0.010 mol) = 438)

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

Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 3-3 (4.4 g, 0.010 mol) was added to give 3.5 g (yield 82%) of Intermediate 3-4 (m / z = 424)

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

Synthesis was conducted in the same manner as in Example 1 (5) to obtain 2.4 g (yield 54%) of Intermediate 3-5 (m / z = 452)

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

Intermediate 3-6 (2.0 g, Yield 50%) was obtained by synthesizing the same method as in Example 1- (6), except that bromoethene (1.4 g, 0.013 mol) was added to Intermediate 3-5 (4.5 g, 0.010 mol) %). (M / z = 397)

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

(Intermediate 3-7) was obtained in the same manner as in Example 1 (1) except that Intermediate 3-6 (4.0 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, 0.012 mol) Yield: 73%). (m / z = 444)

(8) Manufacturing example  8: Synthesis of intermediate 3-8

9-ylboronic acid (2.7 g, 0.012 mol) was added to 1,4-dibromobenzene (2.4 g, 0.010 mol) and the intermediate <3-8 > 2.4 g (yield: 73%). (M / z = 333)

(9) Manufacturing example  9: Synthesis of Compound 3

Synthesis was conducted in the same manner as in Example 1-Preparation Example (2), except that Intermediate 3-7 (2.7 g, 0.008 mol) was added to Intermediate 3-7 (4.4 g, 0.010 mol) 73%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (7.94 / d, 7.93 / s, 7.82 / s, 7.75 / d, 7.74 / m) 2H (8.93 / d, 8.13 / s, 7.91 / d, 7.88 / m, 7.82 / m, 7.39 / m, 1.98 / s) 3H (8.12 / d)

LC / MS: m / z = 571 [(M + 1) ^&lt; ^{+ &}

Example  4: Synthesis of compound 4

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

<Intermediate 4-1> 2.0 (1 g) was obtained by synthesizing 1,1-dibromoethene (1.9 g, 0.010 mol) in Intermediate 1-5 (3.7 g, 0.010 mol) g (yield: 51%). (m / z = 397)

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

3.2 g of Intermediate 4-2 (4.0 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, 0.012 mol) were added thereto in the same manner as in Example 1- Yield: 73%). (m / z = 444)

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

Intermediate 4-3 was synthesized by the same method as in Example 1 (2) except that phenyl boronic acid (1.4 g, 0.012 mol) was added to 1,3,5-tribromobenzene (3.1 g, 0.010 mol) 2.3 g (yield: 73%) was obtained. (M / z = 312)

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

Intermediate 4-4 was synthesized in the same manner as in Example 1 (2) except that naphthalen-1-ylboronic acid (2.1 g, 0.012 mol) was added to Intermediate 4-3 (3.1 g, 0.010 mol) 2.5 g (yield 70%) was obtained. (M / z = 359)

(5) Manufacturing example  5: Synthesis of Compound 4

Synthesis was conducted in the same manner as in Example 1 (2), except that Intermediate 4-4 (2.9 g, 0.008 mol) was added to Intermediate 4-2 (4.4 g, 0.010 mol) 76%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.55 / d, 8.42 / d, 8.13 / s, 8.08 / d, 7.94 / d, 7.75 / d, 7.74 / m, 7.61 / m, 7.41 / m 7.59 / d, 7.51 / m, 7.39 / m, 1.98 / s) 3H (7.91 / d, 7.66 / s)

LC / MS: m / z = 597 [(M + 1) ^&lt; ^{+ &}

Example  5: Synthesis of Compound 5

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

Intermediate 5-1> 2,3-Dibromoethene (1.9 g, 0.010 mol) was added to Intermediate 1-5 (3.7 g, 0.010 mol) in the same manner as in Example 1- g (yield: 58%). (m / z = 397)

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

(Intermediate 5-2) was obtained in the same manner as in Example 1 (1), except that Intermediate 5-1 (4.0 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, Yield: 73%). (m / z = 444)

(3) Manufacturing example  3: Synthesis of Compound 5

To the intermediate 5-2 (4.4 g, 0.010 mol) was added 2- (4-bromophenyl) -9,9-dimethyl-9H-fluorene (2.8 g, 0.008 mol) Synthesis was conducted in the same manner to obtain 4.2 g (yield 71%) of < Compound 5 >.

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.34 / s, 8.13 / s, 7.94 / d, 7.93 / d, 7.87 / d, 7.77 / s, 7.75 / d, 7.74 / m, 7.63 / d D, 7.39 / d) 2H (1.98 / s, 1.72 / s) 3H (7.91 / d, 7.39 / d)

LC / MS: m / z = 587 [(M + 1) ^&lt; ^{+ &}

Example  6: Synthesis of Compound 6

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

Synthesis was conducted in the same manner as in Example 1 (2) to give 3,5-dibromo-2-iodophenol (3.8 g, 0.010 mol) to Intermediate 1-1 (3.0 g, 0.010 mol) -1> 2.5 g (yield: 58%). (M / z = 428)

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

2.2 g (yield 50%) of Intermediate 6-2 (m / z) was obtained by the same method as in Example 1- (3), except that Intermediate 6-1 (4.3 g, 0.010 mol) z = 438)

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

3.4 g (yield 80%) of Intermediate 6-3 was obtained by the same procedure as in Example 1 (4), except that Intermediate 6-2 (4.4 g, 0.010 mol) 424)

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

Synthesis was conducted in the same manner as in Example 1 (5), except that Intermediate 6-3 (4.2 g, 0.010 mol) was added to obtain 2.8 g (yield 61%) of Intermediate 6-4 (m / z = 452)

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

2.1 g (yield: 53%) of Intermediate 6-5 was synthesized in the same manner as in Example 1- (6) except that bromoethene (1.4 g, 0.013 mol) was added to Intermediate 6-4 (4.5 g, 0.010 mol) %). (M / z = 397)

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

3.4 g (Intermediate 6-6) was obtained in the same manner as in Example 1 (1) except that Intermediate 6-5 (4.0 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, Yield: 77%). (m / z = 444)

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

Synthesis was conducted in the same manner as in Example 1 (2), except that phenylboronic acid (1.4 g, 0.012 mol) was added to 1,4-dibromonaphthalene (2.9 g, 0.010 mol) (Yield: 64%). (M / z = 283)

(8) Manufacturing example  8: Synthesis of Compound 6

Synthesis was conducted in the same manner as in Example 1 (2), except that Intermediate 6-7 (2.3 g, 0.008 mol) was added to Intermediate 6-6 (4.4 g, 0.010 mol) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.16 / d, 8.13 / s, 8.12 / d, 7.97 / s, 7.82 / d, 7.41 / m) 2H (8.55 / d, 8.01 / d, 7.79 / d, 7.55 / m, 7.51 / m, 1.98 / s) 3H (7.91 / d, 7.39 /

LC / MS: m / z = 521 [(M + 1) ^&lt; ^{+ &}

Example  7: Synthesis of Compound 7

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

<Intermediate 7-1> 2.8 (1 g) was obtained in the same manner as in Example 1 (1) except that 1,8-dibromoanthracene (3.4 g, 0.010 mol) and bis (pinacolato) dibron g (yield: 73%). (m / z = 384)

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

Intermediate 7-2 (3.0 g, 0.010 mol) was added to Intermediate 7-1 (3.8 g, 0.010 mol) and 3-bromo-2-iodophenol > 2.2 g (yield 52%). (M / z = 428)

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

2.1 g (yield: 48%) of Intermediate 7-3 was obtained by the same method as in Example 1 (3), except that Intermediate 7-2 (4.3 g, 0.010 mol) = 438)

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

Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 7-3 (4.4 g, 0.010 mol) was added to obtain 3.0 g (yield 71%) of Intermediate 7-4 (m / z = 424)

(5) Manufacturing example  5: Synthesis of intermediate 7-5

Synthesis was conducted in the same manner as in Example 1 (5), except that Intermediate 7-4 (4.2 g, 0.010 mol) was added to obtain 2.8 g (yield: 61%) of Intermediate 7-5 (m / z = 452)

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

Intermediate 7-6 (1.9 g, yield 47%) was synthesized by the same method as in Example 1, (6), except that bromoethene (1.4 g, 0.013 mol) was added to Intermediate 7-5 (4.5 g, 0.010 mol) %). (M / z = 397)

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

3.5 g (Intermediate 7-7) was obtained in the same manner as in Example 1 (1) except that Intermediate 7-6 (4.0 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, Yield: 79%). (m / z = 444)

(8) Manufacturing example  8: Synthesis of Compound 7

Compound 7 was synthesized in the same manner as in Example 1 (2) except that 2- (4-bromophenyl) naphthalene (2.3 g, 0.008 mol) was added to Intermediate 7-7 (4.4 g, 0.010 mol) 3.8 g (73% yield) of (m / z = 520)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.13 / s, 8.12 / d, 7.91 / d, 7.87 / d, 7.82 / d, 7.75 / d, 7.74 / m, 7.73 / d, 7.61 / d , 7.58 / d, 7.45 / m) 2H (8.00 / d, 7.59 / m, 1.98 /

LC / MS: m / z = 521 [(M + 1) ^&lt; ^{+ &}

Example  8: Synthesis of Compound 8

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

Intermediate 10-1 (2.8 g, 0.008 mol) was added to Intermediate 5-2 (4.4 g, 0.010 mol) and the same procedure as in Example 1- (2) (Yield: 73%). (M / z = 520)

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

Intermediate 8-2 (2.8 g, 0.010 mol) was synthesized in the same manner as in Example 1- (7) except that N-bromosuccinimide (1.8 g, 0.010 mol) Yield: 47%). (M / z = 599)

(3) Manufacturing example  3: Synthesis of Intermediate 8-3

4.3 g (Intermediate 8-3) was obtained in the same manner as in Example 1 (1) except that Intermediate 8-2 (6.0 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, Yield 66%). (m / z = 646)

(4) Manufacturing example  4: Synthesis of Compound 8

Synthesis was conducted in the same manner as in Example 1 (2), except that Intermediate 1-10 (2.8 g, 0.008 mol) was added to Intermediate 8-3 (6.5 g, 0.010 mol) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.34 / s, 7.94 / d, 7.75 / d, 7.74 / m) 2H (8.55 / d, 8.08 / d, 7.85 / s, 7.76 / s, 7.41 (7.91 / d, 7.39 / d) 4H (7.79 / d, 7.55 / m, 7.51 / m)

LC / MS: m / z = 723 [(M + 1) ^&lt; ^{+ &}

Example  9: Synthesis of Compound 9

(One) Manufacturing example  1: Synthesis of Compound (9)

Synthesis was carried out in the same manner as in Example 1 (2) except that 3-bromo-9,9-dimethyl-9H-xanthene (2.3 g, 0.008 mol) was added to Intermediate 1-8 (4.4 g, 0.010 mol) (Compound 9) (4.2 g, yield 79%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.12 / d, 7.94 / d, 7.82 / d, 7.74 / d, 7.32 / d, 7.26 / d, 7.25 / d, 7.23 / m) 2H (7.09 / d, 1.98 / s, 1.72 / s) 3H (7.91 / d, 7.39 / m)

LC / MS: m / z = 527 [(M + 1) ^&lt; ^{+ &}

Example  10: Synthesis of Compound 10

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

Synthesis was conducted in the same manner as in Example 1 (2), except that phenyl boronic acid (1.4 g, 0.012 mol) was added to 2,4-dibromo-1-chlorobenzene (2.7 g, 0.010 mol) 1> 1.9 g (yield: 73%). (M / z = 264)

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

(10 g, 0.010 mol) was added to Intermediate 10-1 (2.6 g, 0.010 mol), and the intermediate <10-2> was synthesized in the same manner as in Example 1- Yield: 77%). (M / z = 339)

(3) Manufacturing example  3: Synthesis of compound 10

Synthesis was conducted in the same manner as in Example 1 (6), except that Intermediate 10-2 (3.4 g, 0.010 mol) was added to Intermediate 1-7 (4.0 g, 0.010 mol) 82%). (M / z = 655)

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.12 / d, 7.94 / d, 7.82 / d, 7.75 / d, 7.74 / d, 7.50 / d, 7.45 / s, 6.75 / d) 2H (7.52 d, 7.31 / d, 7.41 / m, 7.08 / d, 6.99 / d, 6.61 / d, 1.98 /

LC / MS: m / z = 656 [(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 (6), except that 4-bromodibenzo [b, d] thiophene (2.6 g, 0.010 mol) was added to 3,5-dimethylaniline (1.2 g, 0.010 mol) 11-1> 2.3 g (yield 75%). (M / z = 303)

(2) Manufacturing example  2: Synthesis of Compound 11

(11 g, 0.010 mol) was added to Intermediate 1-7 (4.0 g, 0.010 mol), and 5.1 g (yield: 5.1 g, 83%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 8.12 / d, 7.98 / d, 7.94 / d, 7.82 / d, 7.81 / d, 7.74 / d, 7.52 / m, 7.50 / m , 7.27 / m, 6.86 / d, 6.71 / s) 2H (6.36 / s, 2.34 / s, 1.98 / s)

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

Example  12: Synthesis of Compound 12

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

Synthesis was carried out in the same manner as in Example 1 (2) except that naphthalen-1-ylboronic acid (2.2 g, 0.012 mol) was added to 2-bromo-4-chloro-1-fluorobenzene (2.1 g, 0.010 mol) To obtain 1.9 g (yield: 73%) of Intermediate 12-1. (M / z = 256)

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

2.2 g of Intermediate 12-2 was synthesized in the same manner as in Example 1 (6) except that 4-aminobenzonitrile (1.2 g, 0.010 mol) was added to Intermediate 12-1 (2.6 g, 0.010 mol) Yield: 66%). (M / z = 338)

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

Intermediate 12-3 (5.0 g, 0.010 mol) was added to Intermediate 5-1 (4.0 g, 0.010 mol) in the same manner as in Example 1- (6) (Yield: 77%). (M / z = 654)

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

Intermediate 12-4 was synthesized in the same manner as in Example 1 (7), except that N-bromosuccinimide (1.8 g, 0.010 mol) was added to Intermediate 12-3 (6.5 g, 0.010 mol) Yield: 46%). (M / z = 733)

(5) Manufacturing example  5: Synthesis of Compound 12

7.1 g (yield, 7.1 g, 0.010 mol) was obtained from Intermediate 12-4 (7.3 g, 0.010 mol) synthesized in the same manner as in Example 1- 72%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.12 / d, 7.82 / d, 7.50 / d, 6.94 / d) 2H (8.55 / d, 8.42 / d, 8.08 / d, 8.04 / d, 7.61 7H (7.39 / m), 7.05 / d, 6.87 / s, 6.57 / d, 1.98 /

LC / MS: m / z = 992 [(M + 1) ^&lt; ^{+ &}

Example  13: Synthesis of compound 13

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

Dibenzo [b, d] thiophen-4-amine (3.0 g, 0.010 mol) was added to 1,4-dibromobenzene (2.4 g, 0.010 mol) ) To obtain 3.2 g (yield 70%) of Intermediate 13-1 (m / z = 458)

(2) Manufacturing example  2: Synthesis of Compound 13

Synthesis was conducted in the same manner as in Example 1 (2) to give Intermediate 13-1 (4.6 g, 0.010 mol) and Intermediate 7-7 (3.6 g, 0.008 mol) 71%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.45 / d, 8.13 / s, 8.12 / d, 7.98 / d, 7.94 / d, 7.91 / d, 7.87 / d, 7.82 / d, 7.81 / d 7.56 / d, 7.74 / m, 7.61 / d, 7.52 / m, 7.50 / m, 7.45 / m, 7.39 / d, 7.27 / m, 6.86 / s, 6.71 / , 6.36 / d, 2.34 / s, 1.98 / s)

LC / MS: m / z = 696 [(M + 1) ^&lt; ^{+ &}

Example  14: Synthesis of compound 14

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

Intermediate 14-1> 2.5 (4-bromophenyl) trimethylsilane (2.3 g, 0.010 mol) was added to 4-bromoaniline (1.7 g, 0.010 mol) g (yield: 77%). (m / z = 320)

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

4-bromo-3,3 ', 5,5'-tetrafluorobiphenyl (3.1 g, 0.010 mol) was added to Intermediate 14-1 (3.2 g, 0.010 mol) in the same manner as in Example 1- To obtain 4.2 g (yield 77%) of Intermediate 14-2 (m / z = 544)

(3) Manufacturing example  3: Synthesis of Compound 14

Synthesis was conducted in the same manner as in Example 1 (2) to give Intermediate 14-2 (5.4 g, 0.010 mol) and Intermediate 7-7 (3.6 g, 0.008 mol) 79%).

_{H-NMR (200MHz, CDCl 3} ): δ ppm, 1H (8.13 / s, 8.12 / d, 7.94 / d, 7.91 / d, 7.87 / d, 7.82 / d, 7.75 / d, 7.74 / m, 7.61 / d (7.45 / m, 7.39 / d, 6.64 / s) 2H (7.54 / d, 7.29 / s, 7.15 / d, 7.04 / s, 6.69 / d, 6.61 / d, 1.98 / s)

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

device Example  1: Compound 1 The light- Fluorescent blue host  As a material Organic field Light emitting device manufacturing

CuPc was deposited to 80 nm and α-NPD was deposited to 30 nm on a glass substrate coated with ITO, followed by 25 nm deposition at a deposition rate of 0.1 m / sec by mixing <Compound 1> + <Compound B> 6% ₃ was deposited to 40 nm, LiF was deposited to 1 nm, and Al was deposited to 120 nm in this order. Thus, an organic electroluminescent device was manufactured. At this time, deposition rates of CuPc, α-NPD, Alq ₃ , LiF and Al were 0.5 nm / sec, 0.1 nm / sec, 0.01 nm / sec and 0.5 nm / sec, respectively.

device Example  2 to 9

The organic electroluminescent devices of the device embodiments 2 to 9 were fabricated in the same manner as in the device example 1, except that the compound described in [Table 1] was used instead of the compound 1 described above.

device Comparative Example  One

The organic light emitting diode device for the comparative example was fabricated in the same manner except that Compound A (ADN), which is generally used as a fluorescent host material, was used in place of the compound prepared by the invention in the device structure of the embodiment.

Device Example  10: Compound 10 The light- Fluorescent blue dopant  As a material Organic field Light emitting device manufacturing

CuPc was deposited to a thickness of 80 nm on a glass substrate coated with ITO and α-NPD was deposited to a thickness of 30 nm. Then, the film was formed to a thickness of 25 nm and a deposition rate of 0.1 m / sec by mixing <Compound A> + < ₃ was deposited to 40 nm, LiF was deposited to 1 nm, and Al was deposited to 120 nm in this order. Thus, an organic electroluminescent device was manufactured. At this time, deposition rates of CuPc, α-NPD, Alq ₃ , LiF and Al were 0.5 nm / sec, 0.1 nm / sec, 0.01 nm / sec and 0.5 nm / sec, respectively.

device Example  11-14

An organic electroluminescent device of each of the device embodiments 11 to 14 was fabricated in the same manner as in the device example 10, except that the compound described in [Table 2] was used instead of the compound 10.

device Comparative Example  2

The organic light emitting diode device for the comparative example was fabricated in the same manner except that the compound B, which is generally used as a fluorescent dopant material, was used instead of the compound prepared by the invention in the device structure of the embodiment, The structure is as follows.

The results of comparing the characteristics of the organic electroluminescent devices manufactured according to the device embodiments 1 to 14 and the device comparison examples 1 and 2 are shown in the following Tables 1 and 2.

[Table 1]

[Table 2]

Measurement of driving voltage and luminous efficiency

The organic light emitting device (substrate size: 25 × 25 mm 2 / deposition area: 2 × 2 mm 2) according to the above Examples and Comparative Examples was fixed 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. From the results of the above Examples and Comparative Examples and [Table 1] and [Table 2], it was found that the compounds represented by Chemical Formulas 1 to 14 according to the present invention are more excellent in the driving voltage and luminescence efficiency than those of the conventional blue fluorescent light emitting material It can be seen that it can be usefully used for a display element, a display element, an illumination, and the like.

Claims (10)

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

In the above formula (1)
R ₁ and R ₂ are methyl groups,
R ₃ to R ₁₄ are the same or different and are each independently selected from the group consisting of hydrogen, an alkyl group having 1 to 7 carbon atoms, a group represented by the following formulas (1) and (2)
[Structural formula 1]

[Structural formula 2]

In the above Structural Formulas 1 to 2,
L ₁ and L ₂ are each independently a direct bond or a phenylene group or a naphthylene group (n and m are each an integer of 0 to 2, and when n and m are 2, a plurality of L ₁ and L ₂ are bonded to each other The same or different),
Ar ₁ to Ar ₃ each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms (p and q are integers of 1 to 2 and p And when q is 2, plural * - () are the same or different from each other),
Wherein at least one of R ₁ to R ₁₄ is independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 7 carbon atoms, a group selected from the following formulas (1) and (2)
Each of Ar ₁ to Ar ₃ may be further substituted with one or more substituents, and the substituent may be one or more substituents selected from the group consisting of deuterium, cyano, halogen, alkyl having 1 to 7 carbon atoms, alkylsilyl having 1 to 7 carbon atoms, An alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms and a heteroarylamino group having 3 to 24 carbon atoms . delete delete The method according to claim 1,
[Formula 1] is selected from the following [compounds 1] to [347]:

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. 6. The method of claim 5,
Wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously performing electron transport and electron injection, and a light emitting layer, Wherein at least one layer comprises an organic light-emitting compound represented by the above formula (1). The method according to claim 6,
Wherein the light emitting layer comprises an organic light emitting compound represented by the following formula (1). 8. The method of claim 7,
Wherein the organic light emitting compound represented by Formula 1 is used as a host compound or a dopant compound in the light emitting layer. 9. The method of claim 8,
Wherein the light emitting layer further comprises at least one host compound or a dopant compound other than the organic light emitting compound represented by Formula 1 below. delete

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