KR20090068193A - Organic compound, and organic photoelectric device comprising the same - Google Patents

Abstract

An organic compound and organic photoelectric device containing the same are provided to resolve in organic solvent, generate fluorescence and phosphorescence from red wavelength and blue wavelength. An organic compound is denoted by the chemical formula A. In the chemical formula A, L is subsitituent of the chemical formula A-1 or A-2. An organic photoelectric device comprises a substrate, anode, hole transport layer, light emitting layer, electron transport layer, and cathode. A method for producing the organic photoelectric device using the organic compound comprises: a step of coating a material for anode on the substrate; a step of forming hole transport layer using vacuum evaporation, sputtering or spin coating; a step of forming light emitting layer on the hole transport layer through the method of vacuum evaporation, spin coating, and solution coating method of inkjet printing; a step of forming electron transport layer and cathode on the light emitting layer.

Description

Organic compound, and organic photoelectric device including the same TECHNICAL FIELD

The present invention relates to an organic compound, and an organic photoelectric device including the same, and more particularly, is well dissolved in an organic solvent, and can generate fluorescence and phosphorescence from a red wavelength to a blue wavelength, thereby emitting a light emitting layer of the organic photoelectric device. The present invention relates to an organic compound that can be applied as a host material, and an organic photoelectric device including the same.

An organic photoelectric device has an organic light emitting material in a space between a lower plate having a form in which an ITO transparent electrode pattern is formed as an anode on a transparent glass substrate and an upper plate in which a metal electrode is formed as a cathode on a substrate. And a display device that emits light while a current flows through the organic light emitting material when a predetermined voltage is applied between the transparent electrode and the metal electrode.

The organic light emitting material used in the organic photoelectric device was developed by Eastman Kodak in 1987 for the first time to develop an organic light emitting device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer (Applied Physics Letters). 51, 913, 1987), and in 1987, CW Tang et al. Reported the first devices with practical performance (Applied Physics Letters, 51 (12), 913-915, 1987).

This document describes a structure in which a thin film of a diamine derivative (hole transport layer) and a thin film of tris (8-hydroxy-quinolate) aluminum (Alq ₃ ) are laminated as an organic layer. The Alq ₃ thin film serves as an electron transporting light emitting layer.

In general, an organic photoelectric device has a structure formed on a glass substrate in order of an anode made of a transparent electrode, an organic thin film layer including a light emitting region, and a metal cathode. In this case, the organic thin film layer may include a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, or an electron injection layer, and may further include an electron blocking layer or a hole blocking layer due to the light emission characteristics of the light emitting layer.

When an electric field is applied to the organic photoelectric device having such a structure, holes and electrons are injected from the anode and the cathode, respectively, and the injected holes and electrons are recombined in the light emitting layer through the respective hole transport layer and the electron transport layer to emit light excitons. To form.

The light-excited excitons thus formed emit light while transitioning to ground states.

Light emission is divided into fluorescence using singlet excitons and phosphorescence using triplet states according to its mechanism.

Recently, it has been known that not only fluorescent light emitting materials but also phosphorescent materials can be used as light emitting materials for organic photoelectric devices (DFO'Brien et al., Applied Physics Letters, 74 (3), 442-444, 1999; MA Baldo et al. , Applied Physics letters, 75 (1), 4-6, 1999). These phosphorescent luminescence transfers electrons from the ground state to the excited state and then through the intersystem crossing, After luminescence transition, the triplet excitons are made to emit light while transitioning to the ground state.

In this case, the half-life (luminescence time) is longer than the fluorescence because the triplet excitons cannot directly transition to the ground state because the electron spin undergoes the process of transition to the ground state after the flipping is performed. Has

That is, the emission duration of fluorescence emission is only several nanoseconds, but the phosphorescence emission corresponds to several micro seconds, which is a relatively long time.

In addition, in quantum mechanical terms, when the holes injected from the anode and the electrons injected from the cathode recombine to form a luminescent excitons, the ratio of the singlet and triplet is 1: 3 and the triplet in the organic photoelectric device is triple. Three times more anti-luminescent excitons are generated than single-luminescent excitons.

Therefore, in the case of fluorescence, the probability of singlet excited state is 25% (triple state 75%) and there is a limit of luminous efficiency, while using phosphorescence, the probability of triplet excited state and the probability of singlet excited state 25% In theory, the internal quantum efficiency is up to 100%. Therefore, in the case of using the phosphorescent material, there is an advantage that can achieve a light emission efficiency about four times higher than the fluorescent material.

In the organic light emitting device having the structure as described above, in order to increase the efficiency and stability of the light emitting state, a light emitting pigment (dopant) may be added to the light emitting layer (host).

In such a structure, the efficiency and performance of the light emitting device vary depending on which host material is used for the light emitting layer, and naphthalene, anthracene, phenanthrene, tetracene, pyrene, benzopyrene, chrysene, pisene, Carbazole, fluorene, biphenyl, terphenyl, triphenylene oxide, dihalobiphenyl, trans-stilbene, 1,4-diphenylbutadiene and the like have been suggested as examples of organic host materials.

As a host material, 4,4-N, N-dicarbazole biphenyl (CBP) is mainly used. The compound has a glass transition temperature of 110 ° C. or lower, and a thermal decomposition temperature of 400 ° C. or lower. It is easy to crystallize, and problems such as short circuits and pixel defects are found as a result of the heat resistance test of the device.

In addition, most host materials including CBP have better hole transporting properties, and since the movement of the injected holes is faster than the movement of the injected electrons, the emission efficiency of the device is reduced because excitons are not effectively formed in the emission layer. Phenomenon appears.

Therefore, in order to implement a highly efficient, long-life phosphorescent organic light emitting device, it is necessary to develop a phosphorescent host material having high bipolar characteristics capable of transferring both holes and electrons with high electrical and thermal stability.

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic compound which is well soluble in an organic solvent and can generate fluorescence and phosphorescence from red to blue wavelengths, and thus can be applied as a host material of an organic light emitting layer of an organic photoelectric device.

Still another object of the present invention is to provide an organic photoelectric device including the organic compound.

The technical problems to be achieved by the present invention are not limited to the technical problems mentioned above, and other technical problems not mentioned will be clearly understood by the average person from the following description.

In order to solve the above technical problem, according to one embodiment of the present invention, there is provided an organic compound selected from the group consisting of a compound represented by the formula (A).

[Formula A]

In Formula A, L is a substituent represented by Formula A-1 or Formula A-2,

[Formula A-1]

[Formula A-2]

In Formula A-2, Y ₁ to Y ₃ are each independently selected from the group consisting of CR ″, and N,

In Formula A, X ₁ to X ₂₄ are each independently selected from the group consisting of CR ′ and N,

R ', R'', and R ₁₀ to R ₁₂ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon atoms having 1 to 20 carbon atoms Alkoxy group, substituted or unsubstituted aryl oxy group having 6 to 20 carbon atoms, substituted or unsubstituted heterooxy group having 2 to 20 carbon atoms, substituted or unsubstituted silyl oxy group having 3 to 40 carbon atoms, substituted or unsubstituted An acyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy carbonyl group having 2 to 20 carbon atoms, an acyl oxy group having 2 to 20 carbon atoms substituted or unsubstituted, an acyl amino group having 2 to 20 carbon atoms substituted or unsubstituted, A substituted or unsubstituted alkoxy carbonyl amino group having 2 to 20 carbon atoms, a substituted or unsubstituted anioxycarbonylamino group having 7 to 20 carbon atoms, a substituted or unsubstituted sulfamoyl amino group having 1 to 20 carbon atoms, substituted or Unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 aryl thiol group, substituted or unsubstituted C1-C20 hetero Heterocyclo alkyl thiol, a substituted or unsubstituted ureide group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon amide group having 1 to 20 carbon atoms, and a substituted or unsubstituted carbon group 3 To 40 silyl groups, and

Ar ₁ to Ar ₃ are each independently selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,

Ar 'to Ar' '' are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

A is 0 or 1 when L is a substituent represented by Formula A-1, and 1 is 1 when L is a substituent represented by Formula A-2.

According to another embodiment of the present invention, an organic film is disposed between a pair of electrodes, and the organic film provides an organic photoelectric device including the organic compound.

Other specific details of embodiments of the present invention are included in the following detailed description.

Compounds containing a hole transport material, well soluble in organic solvents and capable of generating fluorescence and phosphorescence from red to blue wavelengths are provided, which can be applied as a host material of an organic light emitting layer of an organic photoelectric device.

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.

According to one embodiment of the present invention, an organic compound selected from the group consisting of compounds represented by the following Formula A is provided.

[Formula A]

In Formula A, L is a substituent represented by Formula A-1 or Formula A-2,

[Formula A-1]

[Formula A-2]

In Formula A-2, Y ₁ to Y ₃ are each independently selected from the group consisting of CR ″, and N,

In Formula A, X ₁ to X ₂₄ are each independently selected from the group consisting of CR ′ and N,

R ', R'', and R ₁₀ to R ₁₂ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon atoms having 1 to 20 carbon atoms Alkoxy group, substituted or unsubstituted aryl oxy group having 6 to 20 carbon atoms, substituted or unsubstituted heterooxy group having 2 to 20 carbon atoms, substituted or unsubstituted silyl oxy group having 3 to 40 carbon atoms, substituted or unsubstituted An acyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy carbonyl group having 2 to 20 carbon atoms, an acyl oxy group having 2 to 20 carbon atoms substituted or unsubstituted, an acyl amino group having 2 to 20 carbon atoms substituted or unsubstituted, A substituted or unsubstituted alkoxy carbonyl amino group having 2 to 20 carbon atoms, a substituted or unsubstituted anioxycarbonylamino group having 7 to 20 carbon atoms, a substituted or unsubstituted sulfamoyl amino group having 1 to 20 carbon atoms, substituted or Unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 aryl thiol group, substituted or unsubstituted C1-C20 hetero Heterocyclo alkyl thiol, a substituted or unsubstituted ureide group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon amide group having 1 to 20 carbon atoms, and a substituted or unsubstituted carbon group 3 To 40 silyl groups, and

Ar ₁ to Ar ₃ are each independently selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,

Ar 'to Ar' '' are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

A is 0 or 1 when L is a substituent represented by Formula A-1, and 1 is 1 when L is a substituent represented by Formula A-2.

In addition, according to one embodiment of the present invention, an organic compound represented by the following Chemical Formulas 1 to 5 is provided.

[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

(In the above formula 1 to 5,

X ₁ to X ₃₂ are each independently selected from the group consisting of CR ′ and N,

Y ₁ to Y ₃ are each independently selected from the group consisting of CR ″, and N,

Ar ₁ to Ar ₄ are each independently selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,

Ar 'to Ar' '' 'are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

R ', R'', and R ₁₀ to R ₁₂ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon atoms having 1 to 20 carbon atoms Alkoxy group, substituted or unsubstituted aryl oxy group having 6 to 20 carbon atoms, substituted or unsubstituted heterooxy group having 2 to 20 carbon atoms, substituted or unsubstituted silyl oxy group having 3 to 40 carbon atoms, substituted or unsubstituted An acyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy carbonyl group having 2 to 20 carbon atoms, an acyl oxy group having 2 to 20 carbon atoms substituted or unsubstituted, an acyl amino group having 2 to 20 carbon atoms substituted or unsubstituted, A substituted or unsubstituted alkoxycarbonylamino group having 2 to 20 carbon atoms, a substituted or unsubstituted anioxycarbonylamino group having 7 to 20 carbon atoms, a substituted or unsubstituted sulfamoyl amino group having 1 to 20 carbon atoms, substituted or unsubstituted A sulfonyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl thiol group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl thiol group having 6 to 20 carbon atoms, a substituted or unsubstituted heterocyclo alkyl thiol having 1 to 20 carbon atoms Group, a substituted or unsubstituted C1-C20 ureide group, a substituted or unsubstituted C1-C20 phosphate amide group, and a substituted or unsubstituted C3-C40 silyl group)

Ar ₁ to Ar ₄ are each independently substituted or unsubstituted carbazole group, substituted or unsubstituted arylamine group, substituted or unsubstituted phenyl group, substituted or unsubstituted tolyl group, substituted or unsubstituted naphthyl group, Substituted or unsubstituted stilbene group, substituted or unsubstituted fluorene group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted diphenylanthra A senyl group, a substituted or unsubstituted dinaphthylanthracenyl group, a substituted or unsubstituted pentaxenyl group, a substituted or unsubstituted bromophenyl group, a substituted or unsubstituted hydroxyphenyl group, a substituted or unsubstituted thienyl group, It is preferably selected from the group consisting of a substituted or unsubstituted pyridyl group, a substituted or unsubstituted azobenzenyl group, and a substituted or unsubstituted ferrocenyl group.

Ar 'to Ar' '' 'are each independently substituted or unsubstituted carbazole group, substituted or unsubstituted arylamine group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted Anthracenyl group, substituted or unsubstituted fluorene group, substituted or unsubstituted thiophene group, substituted or unsubstituted pyrrole group, substituted or unsubstituted pyridine group, substituted or unsubstituted aryloxadiazole group, substituted or It is preferably selected from the group consisting of an unsubstituted triazole group and a substituted or unsubstituted arylsilane group.

In this specification, the substituted arylene group and substituted heteroarylene group are each an alkyl group having 1 to 30 carbon atoms, a halogen group, a haloalkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a hetero group having 2 to 30 carbon atoms, respectively. It means an arylene group substituted with an aryl group, and a hetero arylene group.

Also herein, substituted alkyl groups, substituted alkenyl groups, substituted aryl groups, substituted heteroaryl groups, substituted alkoxy groups, substituted aryl oxy groups, substituted hetero oxy groups, substituted silyl oxy groups, substituted Acyl group, substituted alkoxy carbonyl group, substituted acyl oxy group, substituted acyl amino group, substituted alkoxy carbonyl amino group, substituted anyloxycarbonylamino group, substituted sulfamoyl amino group, substituted sulfonyl group, substituted alkylthiol group , A substituted aryl thiol group, substituted heterocyclo alkyl thiol group, substituted ureide group, substituted phosphate amide group, and substituted silyl group are each an alkyl group having 1 to 30 carbon atoms, a halogen group, a halo having 1 to 30 carbon atoms Alkyl group, alkenyl group, aryl group, heteroaryl group, alkoxy group, aryl oxy group, hetero jade substituted by alkyl group, aryl group having 6 to 30 carbon atoms or heteroaryl group having 2 to 30 carbon atoms Period, silyl oxy group, acyl group, alkoxy carbonyl group, acyl oxy group, acyl amino group, alkoxy carbonyl amino group, anyloxycarbonylamino group, sulfamoyl amino group, sulfonyl group, alkylthiol group, aryl thiol group, heterocycloalkyl thiol group , Uraide group, phosphate amide group, and silyl group.

Also in the context of the present invention, substituted carbazole groups, substituted arylamine groups, substituted phenyl groups, substituted tolyl groups, substituted naphthyl groups, substituted stilbene groups, substituted fluorene groups, substituted anthracenyl groups, substitutions Terphenyl group, substituted pyrenyl group, substituted diphenylanthracenyl group, substituted dinaphthylanthracenyl group, substituted pentacenyl group, substituted bromophenyl group, substituted hydroxyphenyl group, substituted thienyl group, substitution The pyridyl group, the substituted azobenzenyl group, and the substituted ferrocenyl group each have an alkyl group having 1 to 30 carbon atoms, a halogen group, a haloalkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a carbon group having 2 to 30 carbon atoms. Carbazole group substituted by heteroaryl group, arylamine group, phenyl group, tolyl group, naphthyl group, stilbene group, fluorene group, anthracenyl group, terphenyl group, pyrenyl group, diphenylanthracenyl group, dinaphthyl anthracenyl group, Pentacenyl, bro It means a phenyl group, a hydroxyphenyl group, a thienyl group, a pyridyl group, an azo group benje, and ferrocenyl.

In addition, in the specification of the present invention, the substituted thiophene group, substituted pyrrole group, substituted pyridine group, substituted aryloxadiazole group, substituted triazole group, and substituted arylsilane group are each an alkyl group having 1 to 30 carbon atoms, A thiophene group, a pyrrole group, a pyridine group, an aryloxadiazole group, a triazole group, and an aryl substituted with a halogen group, a haloalkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms Means a silane group.

In addition, the term "hetero" in the present specification means that it contains 1 to 3 hetero atoms selected from the group consisting of N, O, S, and P, and the rest are carbon.

The Ar ′ to Ar ″ ″ are each independently an organic compound selected from the group consisting of compounds represented by the following Chemical Formulas 6 to 35.

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

[Formula 27]

[Formula 28]

[Formula 29]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

(In Chemical Formulas 6 to 35,

R ₁ to R ₇₆ are each independently a halogen atom, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted C1-20 alkyl group, substituted or unsubstituted C2-20 Alkenyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted carbon atom 6 Aryl oxy group of 20 to 20, substituted or unsubstituted heterooxy group of 2 to 20 carbon atoms, substituted or unsubstituted silyl oxy group of 3 to 40 carbon atoms, substituted or unsubstituted acyl group of 1 to 20 carbon atoms, substituted or Unsubstituted alkoxycarbonyl group having 2 to 20 carbon atoms, substituted or unsubstituted acyl oxy group having 2 to 20 carbon atoms, substituted or unsubstituted acyl amino group having 2 to 20 carbon atoms, substituted or unsubstituted Alkoxy carbonyl amino group having 2 to 20 carbon atoms, substituted or unsubstituted anoxyoxycarbonylamino group having 7 to 20 carbon atoms, sulfamoyl amino group having 1 to 20 carbon atoms substituted or unsubstituted, substituted or unsubstituted carbon atom 1 to 20 carbon atoms 20 sulfonyl groups, substituted or unsubstituted C1-C20 alkylthiol groups, substituted or unsubstituted C6-C20 aryl thiol groups, substituted or unsubstituted C1-C20 heterocyclo alkyl thiol groups, substituted Or an unsubstituted C1-C20 ureide group, a substituted or unsubstituted C1-C20 phosphate amide group, and a substituted or unsubstituted C3-C40 silyl group,

N ₁ , n ₂ , n ₄ , n ₆ , n ₁₀ , n ₂₁ , n ₂₆ , n ₂₇ , n ₃₅ , n ₃₉ , n ₄₆ , n ₄₇ , n ₄₉ , n ₅₃ , n ₅₉ , n ₆₁ , and n ₆₂ is an integer from 0 to 5,

N ₃ , n ₅ , n ₇ , n ₈ , n ₁₁ , n ₁₂ , n ₁₆ , n ₂₂ , n ₂₃ , n ₂₉ , n ₃₀ , n ₃₁ , n ₃₃ , n ₃₆ , n ₃₇ , n ₄₀ , n ₄₁ to n ₄₄ , n ₄₈ , n ₅₀ to n ₅₂ , n ₅₄ , n ₅₅ , n ₅₇ , n ₆₀ , n ₆₃ , n ₆₅ , n ₆₇ , n ₆₈ , n ₆₉ , n ₇₀ , and n ₇₁ are 0 to Is an integer of 4,

N ₉ , n ₁₃ , n ₁₄ , n ₁₈ , n ₁₉ , n ₂₀ , n ₂₅ , n ₂₈ , n ₃₂ , n ₃₄ , n ₃₈ , n ₄₅ , n ₅₆ , n ₅₈ , and n ₆₆ are 0 to 3 Is an integer of

N ₁₅ and n ₂₄ are integers of 0 to 2)

In particular, at least one of X ₄ , X ₅ , X ₁₂ , X ₁₃ , X ₂₀ , X ₂₁ , X ₂₈ , and X ₂₉ is preferably N.

The compound represented by Chemical Formula 1 may be specifically represented by the following Chemical Formulas 36 to 53.

[Formula 36]

[Formula 37]

[Formula 38]

[Formula 39]

[Formula 40]

[Formula 41]

[Formula 42]

[Formula 43]

[Formula 44]

[Formula 45]

[Formula 46]

[Formula 47]

[Formula 48]

[Formula 49]

[Formula 50]

[Formula 51]

[Formula 52]

[Formula 53]

The compound represented by Chemical Formula 2 may be specifically represented by the following Chemical Formulas 54 to 71.

[Formula 54]

[Formula 55]

[Formula 56]

[Formula 57]

[Formula 58]

[Formula 59]

[Formula 60]

[Formula 61]

[Formula 62]

[Formula 63]

[Formula 64]

[Formula 65]

[Formula 66]

[Formula 67]

[Formula 68]

[Formula 69]

[Formula 70]

[Formula 71]

The compound represented by Chemical Formula 3 may be specifically represented by the following Chemical Formulas 72 to 89.

[Formula 72]

[Formula 73]

[Formula 74]

[Formula 75]

[Formula 76]

[Formula 77]

[Formula 78]

[Formula 79]

[Formula 80]

[Formula 81]

[Formula 82]

[Formula 83]

[Formula 84]

[Formula 85]

[Formula 86]

[Formula 87]

[Formula 88]

[Formula 89]

The compound represented by Chemical Formula 4 may be specifically represented by the following Chemical Formulas 90 to 107.

[Formula 90]

[Formula 91]

[Formula 92]

[Formula 93]

[Formula 94]

[Formula 95]

[Formula 96]

[Formula 97]

[Formula 98]

[Formula 99]

[Formula 100]

[Formula 101]

[Formula 102]

[Formula 103]

[Formula 104]

[Formula 105]

[Formula 106]

[Formula 107]

The compound represented by Chemical Formula 5 may be specifically represented by the following Chemical Formulas 108 to 125.

[Formula 108]

*

[Formula 109]

[Formula 110]

[Formula 111]

[Formula 112]

[Formula 113]

[Formula 114]

[Formula 115]

[Formula 116]

Formula 117

[Formula 118]

Formula 119

[Formula 120]

[Formula 121]

[Formula 122]

[Formula 123]

[Formula 124]

[Formula 125]

In the above formulas 36 to 53 are merely exemplary for formula 1, formulas 54 to 71 are merely exemplary for formula 2, formulas 72 to 89 are merely exemplary of formula 3, formulas 90 to 107 Is merely exemplary for Formula 4, and Formulas 108 to 125 are merely exemplary for Formula 5. In addition, in Formulas 1 to 5, specific examples when X ₁ to X ₃₂ are N are not shown.

The polymerization method of the said organic compound is not specifically limited, Any conventional method of manufacturing an organic compound can be used preferably. However, it is more preferable to use Yamamoto reaction, Suzuki reaction, Stille reaction, Ullman reaction, and the like.

Using the said manufacturing method, the said organic compound can be manufactured by suitably changing reaction temperature, reaction solvent, reaction time, etc.

According to another embodiment of the present invention, an organic film is disposed between a pair of electrodes, and the organic film provides an organic photoelectric device including the organic compound. The organic photoelectric device is preferably an organic light emitting diode.

The organic layer may be a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and is preferably a light emitting layer.

The organic photoelectric device may further include an interlayer layer, a hole transport layer, and an electron transport layer, as well as the most common device configuration of an anode / light emitting layer / cathode.

1 is a view schematically showing a cross-sectional view of an organic photoelectric device 1 according to an embodiment of the present invention. 1 illustrates a structure of an organic photoelectric device including a substrate 11, an anode 12, a hole transport layer 13, a light emitting layer 14, an electron transport layer 15, and a cathode 16.

Referring to Figure 1 describes a method for manufacturing an organic photoelectric device using the organic compound as follows.

First, a material for the anode 12 electrode is coated on the substrate 11.

Here, as the substrate 11, a substrate used in a conventional organic photoelectric device may be used. A glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness may be used.

In addition, as the material for the anode 12 electrode, indium tin oxide (ITO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.

Next, the hole transport layer 13 may be formed on the anode 12 electrode using vacuum deposition, sputtering, or spin coating, and the light emitting layer 14 is vacuum deposited, spin coated, on the hole transport layer 13. It may be formed using a solution coating method such as inkjet printing.

In addition, the electron transport layer 15 is formed on the light emitting layer 14 before the cathode 16 is formed.

At this time, the thickness of the light emitting layer 14 is preferably 5nm to 1㎛, more preferably 10 to 500nm, the thickness of the hole transport layer 13 and the electron transport layer 15 is 10 to 10,000Å respectively. Is preferably.

The electron transport layer 15 may be formed by vacuum deposition, sputtering, or spin coating using a material for forming a conventional electron transport layer 15.

The hole transport layer 13 and the electron transport layer 15 effectively transports the carriers to the light emitting layer 14, thereby increasing the probability of light emission coupling in the light emitting layer 14.

The material for forming the hole transport layer 13 usable in the present invention is not particularly limited, but is a poly (3,4-ethylenedioxy-thiophene) (PEDOT) doped with a poly (styrenesulphonic acid) (PSS) layer. PEDOT: PSS, N, N'-bis (3-methylphenyl) -N, N-diphenyl- [1,1'-biphenyl] -4,4'-diamine (TPD) can be preferably used.

In addition, the material for forming the electron transport layer 15 which may be used in the present invention is not particularly limited, but may be a 2- (4-aluminum trihydroxyquinoline (Alq ₃ ), 1,3,4-oxadiazole derivative. Biphenylyl-5-phenyl-1,3,4-oxadiazole (2- (4-biphenylyl) -5-phenyl-1,3,4-oxadiazole, PBD), a quinoxaline derivative 1,3,4 -Tris [(3-phenyl-6-trifluoromethyl) quinoxalin-2-yl] benzene (1,3,4-tris [(3-penyl-6-trifluoromethyl) quinoxaline-2-yl] benzene, TPQ ), Triazole derivatives and the like can be preferably used.

The organic compound can be used in combination with an organic compound capable of phosphorescence. The phosphorescent organic compound is an organometallic complex capable of phosphorescence from a triplet state, and a metal complex containing at least a periodic table Group VIII metal ion of Mendel (Gregor Johann Mendel) can be preferably used. As the periodic table Group VIII metal ions, metal ions selected from the group consisting of Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, and Pt may be preferably used, and Ir or Pt may be more preferably used. .

Although the example of a specific metal complex is shown to following Chemical formulas 126-128, the said metal complex is not limited to these.

[Formula 126]

[Formula 127]

[Formula 128]

On the other hand, when forming the organic film with the organic compound using a solution coating method, it can be used by mixing with other low molecular host materials. Although the specific example of a low molecular weight host material is given to following general formula 129-132, this invention is not limited to these.

Formula 129]

[Formula 130]

[Formula 131]

[Formula 132]

In addition, the organic compound may be used by blending with polymers having conjugated double bonds such as fluorene-based polymer, polyphenylenevinylene-based, and polyparaphenylene-based, and in some cases, may be used by mixing binder resins.

Examples of the binder resins include polyvinylcarbazole (PVK), polycarbonate, polyester, polyarylate, polystyrene, acrylic polymer, methacryl polymer, polybutyral, polyvinyl acetal, diallyl phthalate polymer, phenol resin, Epoxy resins, silicone resins, polysulfone resins, or urea resins, and the like, which may be used individually or in combination.

Optionally, a hole blocking layer may be formed by vacuum deposition or the like to limit the transfer rate of holes in the emission layer 14 and increase the electron-hole coupling probability.

The material for the cathode 16 electrode is coated on the electron transport layer 15.

As the material for the cathode electrode, lithium (Li), magnesium (Mg), calcium (Ca), aluminum (Al), Al: Li, Ba: Li, or Ca: Li having a small work function is used. do.

The following presents specific embodiments of the present invention. However, the embodiments described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.

In addition, the description is not described herein, so those skilled in the art that can be sufficiently technically inferred, the description thereof will be omitted.

Example 1 Synthesis of M-1

Scheme 1

3.2 g (26 mmol) of 9- (3-bromophenyl) -9-H-fluorene-9-ol (9- (3-bromophenyl) 9-H-fluorene-9-ol) and triphenyl under a nitrogen atmosphere 2.0 g (8.15 mmol) of amine was dissolved in 60 mL of dichloromethane, and 4 mL of boron trifluoride diethyl ether complex (BF ₃ · OEt ₂ ) was slowly added dropwise to prepare a mixture. The mixture was stirred at room temperature for 12 hours and then 60 mL of water was added to terminate the reaction. The reaction was extracted with dichloromethane and washed four times with water, and then the extract solution was dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the dried solution was purified by a silica gel column with a methylene chloride / hexane (1: 2) mixed solvent and recrystallized with a methylene chloride / hexane mixed solvent to give 8.6 g (87.7) of white M-1. %) Obtained.

Example 2 Synthesis of M-2

Scheme 2

3.2 g (26 mmol) of 9- (3-bromophenyl) -9-H-fluorene-9-ol (9- (4-bromophenyl) 9-H-fluorene-9-ol) and triphenyl under a nitrogen atmosphere 2.0 g (8.15 mmol) of amine was dissolved in 60 mL of dichloromethane, and 4 mL of boron trifluoride diethyl ether complex (BF ₃ · OEt ₂ ) was slowly added dropwise to prepare a mixture. The mixture was stirred at room temperature for 12 hours and then 60 mL of water was added to terminate the reaction. The reaction was extracted with dichloromethane and washed four times with water, and then the extract solution was dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the dried solution was purified by a silica gel column with a methylene chloride / hexane (1: 2) mixed solvent and recrystallized with a methylene chloride / hexane mixed solvent to obtain 8.0 g of white M-2 (81.6). %) Obtained.

Example 3 Synthesis of M-3

Scheme 3

A substance (9- (9- (4-tert-butylphenyl) -3-bromo-9H-carbazole-6-yl) -9H-fluorene-9-ol (7.28 g (13 mmol) and triphenylamine) under nitrogen atmosphere 1.0 g (4.07 mmol) was dissolved in 50 mL of dichloromethane, and 2 mL of boron trifluoride diethyl ether complex (BF ₃ · OEt ₂ ) was slowly added dropwise to prepare a mixture, which was stirred at room temperature for 12 hours. 50 mL of water was added to terminate the reaction, and the reaction was extracted with dichloromethane and washed four times with water, and then the extract solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure, followed by methylene chloride. Purified by silica gel column with / hexane (2: 3) mixed solvent to give 6.5 g (85.5%) of white M-3.

Example 4 Synthesis of CISH-1

Scheme 4

In a 100 milliliter round bottom flask equipped with a thermometer, reflux condenser and stirrer, 1.0 g (0.83 mmol) of M-1, (3- (9H-carbazol-9-yl) -5- (4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole ((3- (9H-carbazol-9-yl) -5- (4,4, 2.22 g (4.15 mmol) of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole) and 0.05 g of tetrakistriphenylphosphinepalladium were dissolved in 40 mL of tetrahydrofuran. 20 mL of 20% tetratriethylammonium hydroxide was added thereto, and the mixture was reacted by refluxing at 75 ^° C. for 48 hours.

After the reaction was completed, the reaction was cooled to room temperature, extracted with methylene chloride several times and washed several times with water.

Thereafter, the washed reactant is dried with anhydrous magnesium sulfate, filtered, and then the solvent is removed.

The reaction product from which the solvent was removed was purified by a silica gel column using a methylene chloride / hexane (1: 1) mixed solvent, and then recrystallized in an acetone / hexane mixed solvent to obtain 1.54 g (85%) of white CISH-1.

Example 5 Synthesis of CISH-2

Scheme 5

In a 100 milliliter round bottom flask equipped with a thermometer, reflux condenser and stirrer, 0.8 g (0.66 mmol) of M-2, (3- (9H-carbazol-9-yl) -5- (4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole ((3- (9H-carbazol-9-yl) -5- (4,4, 1.42 g (2.66 mmol) of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole) and 0.06 g of tetrakistriphenylphosphinepalladium are dissolved in 30 mL of tetrahydrofuran (THF). 15 mL of 20% tetratriethylammonium hydroxide was added thereto, and the mixture was reacted by refluxing at 75 ^° C. for 48 hours.

After the reaction was completed, the reaction was cooled to room temperature, extracted with methylene chloride several times and washed several times with water.

Thereafter, the washed reactant is dried with anhydrous magnesium sulfate, filtered, and then the solvent is removed.

The reaction product from which the solvent was removed was purified by a silica gel column with a methylene chloride / hexane (1: 1) mixed solvent to obtain 1.1 g (75.8%) of white CISH-2.

Example 6 Synthesis of CISH-3

Scheme 6

In a 100 milliliter round bottom flask equipped with a thermometer, reflux condenser and stirrer, 1.0 g (0.53 mmol) of M-3, (3- (9H-carbazol-9-yl) -5- (4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole ((3- (9H-carbazol-9-yl) -5- (4,4, 1.03 g (1.92 mmol) of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole) and 0.05 g of tetrakistriphenylphosphinepalladium were dissolved in 30 mL of tetrahydrofuran (THF). 15 mL of 20% tetratriethylammonium hydroxide was added thereto, and the mixture was reacted by refluxing at 75 ^° C. for 48 hours.

After the reaction was completed, the reaction was cooled to room temperature, extracted with methylene chloride several times and washed several times with water.

Thereafter, the washed reactant is dried with anhydrous magnesium sulfate, filtered, and then the solvent is removed.

The reaction product from which the solvent was removed was purified by a silica gel column using a methylene chloride / hexane (1: 1) mixed solvent and recrystallized in acetone to obtain 0.8 g (52.6%) of white CISH-3.

Example 7 Synthesis of CISH-4

Scheme 7

In a 250 milliliter round bottom flask equipped with a thermometer, reflux condenser and agitator, 1.2 g (0.64 mmol) of M-3, 1- (4- (4,4,5,5-tetramethyl-1,3, 2-dioxaborolan-2-yl) phenyl) pyridine (1- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyridine) 0.72 g (2.57) mmol) and 0.05 g of tetrakistriphenylphosphinepalladium were dissolved in 30 mL of THF (tetrahydrofuran), and 15 mL of 20% tetratriethylammonium hydroxide was added thereto, followed by reacting at 75 ^° C. for 48 hours.

After the reaction was completed, the reaction was cooled to room temperature, extracted with methylene chloride several times and washed several times with water.

Thereafter, the washed reactant is dried with anhydrous magnesium sulfate, filtered, and then the solvent is removed.

The reaction product from which the solvent was removed was purified by a silica gel column with a methylene chloride / methanol (9: 1) mixed solvent, and then recrystallized with a methylene chloride / ethyl acetate (94: 6) mixed solvent to give a white color. 0.7 g (52.2%) of CISH-4 were obtained.

Example 8 Synthesis of CISH-5

Scheme 8

In a 250 milliliter round bottom flask equipped with a thermometer, reflux condenser and stirrer, M-3 1.2 g (0.64 mmol), 1- (3- (4,4,5,5-tetramethyl-1,3, 0.72 g of 2-dioxaborolan-2-yl) phenyl) pyridine (1- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyridine) 2.57 mmol) and 0.05 g of tetrakistriphenylphosphinepalladium were dissolved in 30 mL of THF (tetrahydrofuran), and 15 mL of 20% tetratriethylammonium hydroxide was added thereto, followed by reacting at 75 ^° C. for 48 hours.

After the reaction was completed, the reaction was cooled to room temperature, extracted with methylene chloride several times and washed several times with water.

Thereafter, the washed reactant is dried with anhydrous magnesium sulfate, filtered, and then the solvent is removed.

The reaction product from which the solvent was removed was purified by a silica gel column with a methylene chloride / methanol (9: 1) mixed solvent, and then recrystallized with a methylene chloride / ethyl acetate (94: 6) mixed solvent to give a white color. 0.8g (59.7%) of CISH-5 was obtained.

(Performance Measurement of Organic Compounds)

The CISH-5 prepared in Example 8 was measured with ¹ H-NMR using Bruker 300MHz ^® , and the results are shown in FIG. 2. 2, it can be seen that the organic compound prepared in Example 8 is CISH-5.

In addition, after forming a thin film on the glass substrate using the CISH-5, using a HITACHI F-4500 ^® was measured PL (photoluminescence) wavelength is shown in Figure 3 the results. Referring to FIG. 3, it can be seen that the maximum emission wavelength of CISH-5 in the thin film state is 391 nm.

(Production of Organic Photoelectric Device)

An ITO substrate was used as an anode, and poly (3,4-ethylenedioxy-thiophene) (PEDOT) was formed by spin coating on the substrate.

Subsequently, on the PEDOT, Ir (mppy) ₃ was doped with 6 to 7% of dopant in CISH-2 to form a light emitting layer by spin coating.

BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer having a thickness of 50 Å.

Thereafter, Alq ₃ was vacuum deposited on the emission layer to form an electron transport layer having a thickness of 200 Å.

The organic photoelectric device was completed by forming a cathode by sequentially vacuum depositing LiF 10Å and Al 1000Å on the electron transport layer.

Comparative reference device structure used PVK as a polymer host.

Evaluation device structure is Al (1000 mW) / LiF (10 mW) / Alq ₃ (200 mW) / BAlq (50 mW) / EML (CISH-2 + Ir (mppy) ₃ ) / PEDOT / ITO (1500 mW) Was Al (1000 mV) / LiF (10 mV) / Alq ₃ (200 mV) / BAlq (50 mV) / EML (PVK + Ir (mppy) ₃ ) / PEDOT / ITO (1500 mV).

(Performance Measurement of Organic Photoelectric Device)

In the organic photoelectric device manufactured according to Example 8, a change in luminance and a change in efficiency according to a change in voltage were measured, and the results are shown in FIGS. 4 and 5, respectively.

In addition, the threshold voltage of the organic photoelectric device manufactured according to Example 7, Example 8 and the driving voltage, current efficiency, and power efficiency at 1000 nits were measured, and the results are shown in Table 1 below.

TABLE 1

Type of device Organic compounds Threshold Voltage (V) Measurement result at 1000nit Drive voltage (V) Current efficiency (cd / A) Power Efficiency (lm / W) Green CISH-4 (Example 7) 4.8 9.4 11.12 3.72 CISH-5 (Example 8) 5.0 9.8 11.78 3.77

4, 5, and Table 1, it can be seen that the organic compound according to the present invention can be used as a host material for an organic photoelectric device.

The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

1 is a cross-sectional view of an organic photoelectric device according to an embodiment of the present invention.

2 is a graph showing the ¹ H-NMR spectrum of the organic compound prepared in Example 8 of the present invention.

Figure 3 is a graph showing the PL (photoluminescence) wavelength of the organic compound prepared in Example 8 of the present invention.

4 is a graph showing a change in luminance according to the voltage of an organic photoelectric device including the organic compound prepared in Example 8 of the present invention.

5 is a graph showing a change in efficiency according to a voltage of an organic photoelectric device including the organic compound prepared in Example 8 of the present invention.

<Explanation of symbols for the main parts of the drawings>

11: substrate 12: anode

13: hole transport layer 14: organic light emitting layer

15: electron transport layer 16: cathode

Claims (8)

An organic compound selected from the group consisting of compounds represented by the formula (A): [Formula A]

In Formula A, L is a substituent represented by Formula A-1 or Formula A-2, [Formula A-1]

[Formula A-2]

In Formula A-2, Y ₁ to Y ₃ are each independently selected from the group consisting of CR ″, and N, In Formula A, X ₁ to X ₂₄ are each independently selected from the group consisting of CR ′ and N, R ', R'', and R ₁₀ to R ₁₂ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon atoms having 1 to 20 carbon atoms Alkoxy group, substituted or unsubstituted aryl oxy group having 6 to 20 carbon atoms, substituted or unsubstituted heterooxy group having 2 to 20 carbon atoms, substituted or unsubstituted silyl oxy group having 3 to 40 carbon atoms, substituted or unsubstituted An acyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy carbonyl group having 2 to 20 carbon atoms, an acyl oxy group having 2 to 20 carbon atoms substituted or unsubstituted, an acyl amino group having 2 to 20 carbon atoms substituted or unsubstituted, A substituted or unsubstituted alkoxy carbonyl amino group having 2 to 20 carbon atoms, a substituted or unsubstituted anioxycarbonylamino group having 7 to 20 carbon atoms, a substituted or unsubstituted sulfamoyl amino group having 1 to 20 carbon atoms, substituted or Unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 aryl thiol group, substituted or unsubstituted C1-C20 hetero Heterocyclo alkyl thiol, a substituted or unsubstituted ureide group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon amide group having 1 to 20 carbon atoms, and a substituted or unsubstituted carbon group 3 To 40 silyl groups, and Ar ₁ to Ar ₃ are each independently selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, Ar 'to Ar' '' are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, A is 0 or 1 when L is a substituent represented by Formula A-1, and 1 is 1 when L is a substituent represented by Formula A-2. The method of claim 1, Ar ₁ to Ar ₃ are each independently substituted or unsubstituted carbazole group, substituted or unsubstituted arylamine group, substituted or unsubstituted phenyl group, substituted or unsubstituted tolyl group, substituted or unsubstituted naphthyl group, Substituted or unsubstituted stilbene group, substituted or unsubstituted fluorene group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted diphenylanthra A senyl group, a substituted or unsubstituted dinaphthylanthracenyl group, a substituted or unsubstituted pentaxenyl group, a substituted or unsubstituted bromophenyl group, a substituted or unsubstituted hydroxyphenyl group, a substituted or unsubstituted thienyl group, A substituted or unsubstituted pyridyl group, a substituted or unsubstituted azobenzenyl group, and a substituted or unsubstituted ferrocenyl group, Ar 'to Ar' '' are each independently a substituted or unsubstituted carbazole group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl group, substituted or unsubstituted fluorene group, substituted or unsubstituted thiophene group, substituted or unsubstituted pyrrole group, substituted or unsubstituted pyridine group, substituted or unsubstituted aryloxadiazole group, substituted or unsubstituted An organic compound selected from the group consisting of a substituted triazole group, and a substituted or unsubstituted arylsilane group. The method of claim 1, The Ar ′ to Ar ′ ″ are each independently selected from the group consisting of compounds represented by the following Chemical Formulas 6 to 35. [Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

[Formula 27]

[Formula 28]

[Formula 29]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

(In Chemical Formulas 6 to 35, R ₁ to R ₇₆ are each independently a halogen atom, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted C1-20 alkyl group, substituted or unsubstituted C2-20 Alkenyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted carbon atom 6 Aryl oxy group of 20 to 20, substituted or unsubstituted heterooxy group of 2 to 20 carbon atoms, substituted or unsubstituted silyl oxy group of 3 to 40 carbon atoms, substituted or unsubstituted acyl group of 1 to 20 carbon atoms, substituted or Unsubstituted alkoxycarbonyl group having 2 to 20 carbon atoms, substituted or unsubstituted acyl oxy group having 2 to 20 carbon atoms, substituted or unsubstituted acyl amino group having 2 to 20 carbon atoms, substituted or unsubstituted Alkoxy carbonyl amino group having 2 to 20 carbon atoms, substituted or unsubstituted anoxyoxycarbonylamino group having 7 to 20 carbon atoms, sulfamoyl amino group having 1 to 20 carbon atoms substituted or unsubstituted, substituted or unsubstituted carbon atom 1 to 20 carbon atoms 20 sulfonyl groups, substituted or unsubstituted C1-C20 alkylthiol groups, substituted or unsubstituted C6-C20 aryl thiol groups, substituted or unsubstituted C1-C20 heterocyclo alkyl thiol groups, substituted Or an unsubstituted C1-C20 ureide group, a substituted or unsubstituted C1-C20 phosphate amide group, and a substituted or unsubstituted C3-C40 silyl group, N ₁ , n ₂ , n ₄ , n ₆ , n ₁₀ , n ₂₁ , n ₂₆ , n ₂₇ , n ₃₅ , n ₃₉ , n ₄₆ , n ₄₇ , n ₄₉ , n ₅₃ , n ₅₉ , n ₆₁ , and n ₆₂ is an integer from 0 to 5, N ₃ , n ₅ , n ₇ , n ₈ , n ₁₁ , n ₁₂ , n ₁₆ , n ₂₂ , n ₂₃ , n ₂₉ , n ₃₀ , n ₃₁ , n ₃₃ , n ₃₆ , n ₃₇ , n ₄₀ , n ₄₁ to n ₄₄ , n ₄₈ , n ₅₀ to n ₅₂ , n ₅₄ , n ₅₅ , n ₅₇ , n ₆₀ , n ₆₃ , n ₆₅ , n ₆₇ , n ₆₈ , n ₆₉ , n ₇₀ , and n ₇₁ are 0 to Is an integer of 4, N ₉ , n ₁₃ , n ₁₄ , n ₁₈ , n ₁₉ , n ₂₀ , n ₂₅ , n ₂₈ , n ₃₂ , n ₃₄ , n ₃₈ , n ₄₅ , n ₅₆ , n ₅₈ , and n ₆₆ are 0 to 3 Is an integer of N ₁₅ and n ₂₄ are integers of 0 to 2) The method of claim 1, At least one of X ₄ , X ₅ , X ₁₂ , X ₁₃ , X ₂₀ , and X ₂₁ is N. An organic compound. An organic film positioned between the pair of electrodes, The organic film is an organic photoelectric device comprising the organic compound of claim 1 to claim 4. The method of claim 5, The organic film is an organic photoelectric device that is a light emitting layer. The method of claim 5, The organic film is an organic photoelectric device is selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, and a combination thereof. The method of claim 5, The organic film is an organic photoelectric device is selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and combinations thereof.

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