KR102105654B1 - Compounds for organic electroluminescence device and organic electronic devices using the same - Google Patents

Abstract

Disclosed is a compound for an organic electroluminescent device, which is excellent in luminous efficiency, a pyrene-based compound containing an ether bond, and an organic electronic device comprising the compound for an organic electroluminescent device.

Description

Compounds for organic electroluminescent devices, and organic electronic devices using the same {Compounds for organic electroluminescence devices and organic electronic devices using the same}

The present invention relates to a compound for an organic electroluminescent device, and an organic electronic device using the same, more specifically, a compound for an organic electroluminescent device, which is a pyrene-based compound containing an ether bond having excellent control of luminous efficiency, and the organic electroluminescence It relates to an organic electronic device comprising a compound for a light emitting device.

In general, organic light emitting diodes (OLEDs) are composed of a cathode, an anode, and an organic material layer interposed between the cathode and the anode. The overall structure of the device is a transparent ITO anode, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EL), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), It is formed of a cathode such as LiAl, and, if necessary, one or two of the organic material layers may be omitted. When an electric field is applied between the configured electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and when the excited state returns to the ground state, energy is emitted as light.

These luminescent materials are largely divided into fluorescence and phosphorescence, and the method of forming the luminescent layer is a method of doping phosphorescence (organic metal) to a fluorescent host (pure organic substance) and a method of doping a fluorescent dopant (an organic substance containing nitrogen, etc.) to the fluorescent host. And a method for realizing a long wavelength using a dopant (DCM, Rubrene, DCJTB, etc.) for the light emitter. Through such doping, it is trying to improve the emission wavelength, efficiency, driving voltage, and lifetime. In general, materials for forming a light-emitting layer include benzene, naphthalene, florene, spiroflorene, anthracene, pyrene, and carbazole, and ligands such as phenyl, biphenyl, naphthalene, and heterocycle, and ortho, meta, and para. The bonding sites and substituted structures of amine, cyanide, fluorine, methyl, and trimethyl are substituted.

The compounds are pyrene-based compounds, and DP (2,2'-bipyrene) exhibits a longer wavelength of luminescence than blue of 490 nm (Journal of Luminescence 124 (2007) 93-98), p-Bpye (1, 4-di (pyren-1-yl) benzene) showed light blue color of 474nm (0.14 0.20) and 6.9cd / A (at 8.0V) emission efficiency as a result of device test (Adv. Funct. Mater. 2008, 18, 67 -75), TPB3 (1,3,5-tri (pyren-1-yl) benzene) showed the emission wavelength of 479nm (in CH2Cl2) long wavelength (Synthetic Metals 143 (2004) 89-96), TPB4 (1 , 1 ', 2' ', 2' ''-(benzene-1,2,4,5-tetrayl) tetrapyrene) showed green emission at 576 nm (Synthetic Metals 143 (2004) 89-96). The aromatic pyrenes 2H (N1, N1, N6, N6-tetraphenylpyrene-1,6-diamine) and 2OMe (N1, N6-bis (4-methoxyphenyl) -N1, N6-diphenylpyrene-1,6-diamine) are 472nm each. And a light emission wavelength of 513 nm. (J. Org. Chem., 2009, 74, 8472)

Currently, as the screen of the display progresses in the direction of enlargement, in the case of OLED, materials with more delicate and vivid colors are required. Among them, the current problem and the material to be solved are blue, and high-performance luminescent materials are required from the current sky blue (470-480 nm) to blue (455-460 nm) and deep blue (<455 nm) directions. In addition, in addition to the color coordinates of the emission wavelength, it requires high luminous efficiency at a low driving voltage of the device and high glass transition temperature, which is a chemical structural thermal stability of the material.

Prior arts for pyrene-based compounds include Republic of Korea Application Nos. 10-2005-7017372, 10-2007-702349, and 10-2009-7025536. However, for the development of organic electroluminescence technology, there is still a need to develop a compound having a luminescence wavelength, high performance, luminous efficiency, and thermal stability.

The problem to be solved by the present invention is that it is easy to control the molecular weight of the compound and secure thermal stability accordingly, and also has no influence of wavelength shift due to an increase in molecular weight, structurally excellent in luminous efficiency, and organic showing a three-dimensional structure It is to provide a compound for an electroluminescent device.

In addition, the problem to be solved by the present invention is to provide an organic electronic device comprising the compound for an organic electroluminescent device.

According to an aspect of the present invention, a compound for an organic electroluminescent device represented by the following Chemical Formula 1 is provided:

[Formula 1]

In Chemical Formula 1,

Ar ₁ to Ar ₃ are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, and X is a substituted or unsubstituted pyrene (pyrene) ) Group, R ₁ to R ₄ are each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted carbon atom number 7 An amino group substituted with an aryl group of 40 to 40, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, R ₁ and R ₂ or R ₃ and R ₄ Can fuse with each other to form a substituted or unsubstituted ring.

L ₁ , and L ₂ are integers of 0 or 3, m ₁ and m ₂ are integers of 0 to 2 , and m ₁ + m ₂ ≥ 1.

At this time, when m ₁ is 0, Ar ₁ ′ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms,

When m ₁ is 1, Ar ₁ ′ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms,

When m ₁ is 2, Ar ₁ ′ is a substituted or unsubstituted trivalent arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted trivalent heterocyclic group having 5 to 40 carbon atoms,

In this case, when m ₂ is 0, Y ₂ is -N (R ')-Ar "-(where Ar" is each independently of each other independently substituted or unsubstituted aryl group having 6 to 40 carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 40 carbon atoms, R 'is substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, substituted or An amino group substituted with an unsubstituted aryl group having 7 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms),

When m ₂ is 1, it is a simple bond, -N (R ')-Ar "-(where Ar" is each independently of each other independently substituted or unsubstituted arylene group having 6 to 40 carbon atoms, substituted or Unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, R 'is substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, substituted or unsubstituted An amino group substituted with an aryl group having 7 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms),

When m ₂ is 2, it is -N (R ')-Ar "-(where Ar" is each independently of each other independently substituted or unsubstituted trivalent arylene group having 6 to 40 carbon atoms, substituted or unsubstituted) Is a trivalent heterocyclic group having 5 to 40 carbon atoms, and R 'is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted carbon An amino group substituted with an aryl group having 7 to 40 atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms)

Y ₁ is a simple bond, -Ar'- or -Ar'-O- (Ar 'is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent complex having 5 to 40 carbon atoms. Ventilation, R 'is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted amino group having 7 to 40 carbon atoms aryl group , Substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms).

The compound for an organic electroluminescent device may be represented by the following Chemical Formula 2 or Chemical Formula 3:

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,

Ar ₁ to Ar ₆ , and Ar ₈ are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, and L ₁ , L ₂ , L ₃ and L ₄ are integers from 0 to 3. R ₁ to R ₉ are each independently of each other a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted aryl having 7 to 40 carbon atoms. An amino group substituted with a group, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms, and R ₁ and R ₂ or R ₃ and R ₄ and R ₅ and R ₆ or R ₈ and R ₉ may be fused to each other to form a substituted or unsubstituted ring. X is a substituted or unsubstituted Pyrene group. n ₁ and n ₂ are integers of 0 or 1, and n ₁ + n ₂ ≥ 1.

At this time, when n ₁ is 0, Ar ₅ ′ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms,

When n ₁ is 1, Ar ₅ ′ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms,

When n ₂ is 0, Ar ₇ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms,

When n ₂ is 1, Ar ₇ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms.

According to another aspect of the present invention, an organic electronic device including a first electrode, a second electrode, and one or more organic material layers disposed between the electrodes, wherein at least one or more of the organic material layers is a compound for the organic electroluminescent device It provides an organic electronic device comprising a.

The compound for an organic electroluminescent device according to an embodiment of the present invention is a pyrene-based compound containing an ether bond, and after improving the luminous efficiency of aromatic pyrene, thermal stability is controlled by adjusting the type and molecular weight of the compound formed by ether bonding. It is easy to secure and can form a three-dimensional structure. In addition, when two amines are directly introduced into pyrene, most of them exhibit a long wavelength of 470 nm or more (J. Org. Chem., 2009, 74, 8472).

However, the compound for an organic electroluminescent device according to the present invention uses a single amine to control the luminescence efficiency and emission wavelength of pyrene, and then introduces another amine compound using an ether bond, thereby reducing HOMO by the amine compound ( There is an advantage in that an efficient dopant can be developed by adjusting the hole value. As a result, the organic electronic device including the compound for an organic electroluminescent device has high luminance, excellent heat resistance, long life and high efficiency.

Hereinafter, the present invention will be described in more detail. The following detailed description is given by taking an example of the present invention and the present invention is not limited thereto.

According to an aspect of the present invention, there is provided a compound for an organic electroluminescent device represented by Formula 1 below:

[Formula 1]

In Chemical Formula 1,

Ar ₁ to Ar ₃ are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, and X is a substituted or unsubstituted pyrene (pyrene) ) Group, R ₁ to R ₄ are each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted carbon atom number 7 An amino group substituted with an aryl group of 40 to 40, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, R ₁ and R ₂ or R ₃ and R ₄ Can fuse with each other to form a substituted or unsubstituted ring.

L ₁ , and L ₂ are integers of 0 or 3, m ₁ and m ₂ are integers of 0 to 2 , and m ₁ + m ₂ ≥ 1.

At this time, when m ₁ is 0, Ar ₁ ′ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms,

When m ₁ is 1, Ar ₁ ′ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms,

When m ₁ is 2, Ar ₁ ′ is a substituted or unsubstituted trivalent arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted trivalent heterocyclic group having 5 to 40 carbon atoms,

In this case, when m ₂ is 0, Y ₂ is -N (R ')-Ar "-(where Ar" is each independently of each other independently substituted or unsubstituted aryl group having 6 to 40 carbon atoms, Substituted or unsubstituted monovalent heterocyclic group having 5 to 40 carbon atoms, R 'is substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, substituted or An amino group substituted with an unsubstituted aryl group having 7 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms),

When m ₂ is 1, it is a simple bond, -N (R ')-Ar "-(where Ar" is each independently of each other independently substituted or unsubstituted arylene group having 6 to 40 carbon atoms, substituted or Unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, R 'is substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, substituted or unsubstituted An amino group substituted with an aryl group having 7 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms),

When m ₂ is 2, it is -N (R ')-Ar "-(where Ar" is each independently of each other independently substituted or unsubstituted trivalent arylene group having 6 to 40 carbon atoms, substituted or unsubstituted) Is a trivalent heterocyclic group having 5 to 40 carbon atoms, and R 'is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted carbon An amino group substituted with an aryl group having 7 to 40 atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms)

Y ₁ is a simple bond, -Ar'- or -Ar'-O- (Ar 'is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent complex having 5 to 40 carbon atoms. Ventilation, R 'is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted amino group having 7 to 40 carbon atoms aryl group , Substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms).

In addition, the compound for an organic electroluminescent device may be represented by the following Chemical Formula 2 or Chemical Formula 3:

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,

Ar ₁ to Ar ₆ , and Ar ₈ are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, and L ₁ , L ₂ , L ₃ and L ₄ are integers from 0 to 3. R ₁ to R ₉ are each independently of each other a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted aryl having 7 to 40 carbon atoms. An amino group substituted with a group, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms, and R ₁ and R ₂ or R ₃ and R ₄ and R ₅ and R ₆ or R ₈ and R ₉ may be fused to each other to form a substituted or unsubstituted ring. X is a substituted or unsubstituted Pyrene group. n ₁ and n ₂ are integers of 0 or 1, and n ₁ + n ₂ ≥ 1.

At this time, when n ₁ is 0, Ar ₅ ′ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms,

When n ₁ is 1, Ar ₅ ′ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms,

When n ₂ is 0, Ar ₇ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms,

When n ₂ is 1, Ar ₇ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms.

In addition, specifically, the compound for an organic electroluminescent device may be represented by the following formula (4):

[Formula 4]

In Chemical Formula 4,

Ar ₉ and Ar ₁₀ are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, and L ₅ is an integer from 0 to 3 to be. R ₁₀ to R ₁₃ are each independently of each other a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted aryl having 7 to 40 carbon atoms. Amino group substituted with a group, substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms, R ₁₀ and R ₁₁ or R ₁₂ and R ₁₃ are fused to each other and substituted Or it may form an unsubstituted ring. X is a substituted or unsubstituted Pyrene group.

Ar ₁ , Ar ₂ , Ar ₃ , Ar 'Ar ”of Formula 1, and Ar ₁ to Ar ₁₀ of Formulas 2 to 4 may each independently be selected from the following Formula.

In the above, Z and Y may be the same or different from each other, a hydrogen atom, a cyan atom, a halogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted Or an unsubstituted aralkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 40 carbon atoms, a substituted or unsubstituted aralkylthio group having 7 to 40 carbon atoms, a substituted or unsubstituted carbon Aryl group having 6 to 40 atoms, substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, substituted or unsubstituted aryl having 6 to 40 carbon atoms It is a thio, substituted or unsubstituted aminoaryl group having 6 to 40 carbon atoms, an amino group, a cyano group, a silyl group, and a phosphine oxide group.

The definition of the substituent used in the present specification is as follows.

, 시아노기, 치환 또는 비치환된 아미노기(-NH₂, -NH(R), -N(R')(R''), R'과 R"은 서로 독립적으로 탄소수 1 내지 10의 알킬기임), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, C1-C20의 알킬기, C1-C20의 할로겐화된 알킬기, C1-C20의 알케닐기, C1-C20의 알키닐기, C1-C20의 헤테로알킬기, C6-C20의 아릴기, C6-C20의 아릴알킬기, C6-C20의 헤테로아릴기, 또는 C6-C20의 헤테로아릴알킬기로 치환될 수 있다. 이러한 알킬기의 예로서 메틸, 에틸, 프로필, 2-프로필, n-부틸, 이소-부틸, tert-부틸, 펜틸, 헥실, 도데실, 플루오로메틸, 디플루오로메틸, 트리플루오로메틸, 클로로메틸, 디클로로메틸, 트리클로로메틸, 요오도메틸, 브로모메틸 등을 들 수 있다. "Alkyl group" means a straight or branched chain saturated monovalent hydrocarbon moiety of a carbon atom. One or more hydrogen atoms contained in the alkyl group is a halogen atom, a silyl group, a phosphine oxide group, a hydroxyl group, -SH, a nitro group,

, Cyano group, substituted or unsubstituted amino group (-NH ₂ , -NH (R), -N (R ') (R''),R' and R "are each independently an alkyl group having 1 to 10 carbon atoms) , Amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-C20 alkyl group, C1-C20 halogenated alkyl group, C1-C20 alkenyl group, C1-C20 alkynyl group, C1-C20 It may be substituted with a heteroalkyl group, a C6-C20 aryl group, a C6-C20 arylalkyl group, a C6-C20 heteroaryl group, or a C6-C20 heteroarylalkyl group, such as methyl, ethyl, propyl, 2-propyl, n-butyl, iso-butyl, tert-butyl, pentyl, hexyl, dodecyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, iodomethyl , Bromomethyl, and the like.

"Aryl group" means a monovalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety, and one or more hydrogen atoms of the aryl group can be substituted with the same substituents as the alkyl group. The aromatic portion of the aryl group contains only carbon atoms. Examples of the aryl group include phenyl, naphthalenyl and fluorenyl.

"Heterocyclic group" means a monovalent monocyclic or bicyclic aromatic radical containing 1, 2 or 3 heteroatoms selected from N, O, or S, and the remaining ring atoms being C. The term also refers to a monovalent monocyclic or bicyclic aromatic radical in which a hetero atom in the ring is oxidized or quaternized to form, for example, an N-oxide or quaternary salt. Representative examples include thienyl, benzothienyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, imidazolyl, furanyl, benzofuranyl, thiazolyl, isoxazoline, Benz isoxazoline, benzimidazolyl, triazolyl, pyrazolyl, pyrrolyl, indolyl, 2-pyridonyl, N-alkyl-2-pyridonyl, pyrazinonyl, pyridazinonyl, pyrimidinonyl , Oxazolonyl and their corresponding N-oxides (eg pyridyl N-oxide, quinolinyl N-oxide), quaternary salts thereof, and the like. One or more hydrogen atoms in the heterocyclic group can be substituted with the same substituents as for the alkyl group.

The "amino group substituted with an aryl group" may also be referred to as "arylamino", which is one or more hydrogen atoms of the amino group substituted with an aryl group, wherein at least one hydrogen atom of the aryl group is a substituent similar to that of the aryl group. Is replaceable.

"Aralkyl" or "arylalkyl" means that at least one hydrogen atom of the alkyl group defined above is substituted with an aryl group, and one or more hydrogen atoms of the aralkyl group can be substituted with the same substituents as for the alkyl group. Examples include benzyl, benzhydryl and trityl.

"Alkoxy group", "aralkyloxy group", and "aryloxy group" refer to a form in which oxygen is further contained at the linking site of the linking group of the aforementioned "alkyl group", "aralkyl group" and "aryl group", respectively. "Alkylthio group" and "arylthio group" refer to a form in which sulfur is further contained in a linking group of an "aralkyl group" or "aryl group".

"Binding" refers to a site connected only by a simple bond in which no substituent is inserted.

More specifically, the compound for an organic electroluminescent device according to an embodiment of the present invention may be represented by Chemical Formulas 5 to 13:

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

.

.

According to another aspect of the present invention, there is provided a method for preparing a compound for an organic electroluminescent device as described above, which includes an amination reaction or a suzuki coupling reaction step.

In addition, a method for preparing a pyrene-based compound according to an embodiment of the present invention includes an amination reaction step of a halogen compound and an amine compound as starting materials; A nucleophilic substitution reaction step of the synthesized amino group-containing halogen compound and a sodium oxide compound; And performing an amination reaction using the synthesized compound.

In addition, in the above-described manufacturing method, a step of suzuki coupling reaction or amination and nucleophilic substitution reaction may be further included in the middle.

Specifically, one form of the method for producing the compound for an organic electroluminescent device, as shown in Reaction Scheme 1 below, using (di) halogen-pyrene as a starting material, (i) and (ii) Suzuki coupling, (i) amination, (Iii) a nucleophilic substitution reaction step and (iii) an amination step.

[Scheme 1]

(X = pyrene, Y 'and Z' = halogen or boronic acid [B (OH) ₂ ], W '= amine [NH ₂ ])

In addition, another form of the method for preparing the compound for an organic electroluminescent device is (i) and (ii) Suzuki coupling, (i) amination, using di-halogen-pyrene as a starting material, as shown in Reaction Scheme 2 below. (I) and (i) a nucleophilic substitution reaction step and (i) and (i) an amination step.

[Scheme 2]

(X = pyrene, Y 'and Z' = halogen or boronic acid [B (OH) ₂ ], W '= amine [NH ₂ ])

Another method for producing an organic electroluminescent device compound, as shown in Reaction Scheme 3 below, using di-halogen-pyrene as a starting material, (i) Suzuki coupling, (ii) amination, (i) nucleophilic substitution reaction step And (iii) amination.

[Scheme 3]

According to an aspect of the present invention, an organic electronic device including a first electrode, a second electrode, and one or more organic material layers disposed between the electrodes, wherein at least one or more of the organic material layers is represented by the formula An organic electronic device comprising a compound for an electroluminescent device is provided.

The organic electroluminescent device compound may be included in the organic material layer in the form of a single material or a mixture of different materials.

The organic layer includes a hole injection layer, a hole transport layer, a function layer having a hole injection function and a hole transport function simultaneously, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron transport function and an electron injection function simultaneously It may include at least one of the functional layer having. At least one of the hole injection layer, the hole transport layer, and the functional layer having the hole injection function and the hole transport function at the same time, in addition to a conventional hole injection material, a hole transport material, and a material simultaneously performing the hole injection and transport function, charge- It may further include a product.

"Organic layer" in the present specification is a term for all the layers interposed between the first electrode and the second electrode of the organic electronic device.

For example, the organic material layer includes a light emitting layer, and the light emitting layer may include at least one of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. Here, the light emitting layer includes the compound for an organic electroluminescent device, i) the fluorescent host is a compound for the organic electroluminescent device, ii) the fluorescent dopant is a compound for the organic electroluminescent device, or iii ) Each of the fluorescent host and the fluorescent dopant may be a compound for the organic electroluminescent device.

The light emitting layer may be a red, green or blue light emitting layer. For example, the light emitting layer may be a blue light emitting layer. At this time, the compound for an organic electroluminescent device may be used as a blue host and / or a blue dopant to provide an organic electronic device having high efficiency, high brightness, high color purity, and long life.

In addition, the organic material layer includes an electron transport layer, and the compound for the organic electroluminescent device may be included in the electron transport layer. Here, the electron transport layer may further include a metal-containing compound in addition to the compound for an organic electroluminescent device.

The organic material layer includes both a light emitting layer and an electron transport layer, and the compound for the organic electroluminescent device in each of the light emitting layer and the electron transport layer (the compound for the organic electroluminescent device included in the light emitting layer and the electron transport layer may be the same or different from each other) May be included.

The organic electronic device may be manufactured by a conventional manufacturing method and material of an organic electronic device, except that the compound for an organic electroluminescent device of Formula 1 is used.

As an embodiment according to an aspect of the present invention, the organic electronic device is an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-Paper), an organic photoreceptor (OPC) or an organic transistor (OTFT). You can.

The organic light emitting device uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to deposit a metal or conductive metal oxide or an alloy thereof on a substrate to deposit an anode. It can be produced by forming and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition to this method, an organic light emitting device may be made 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, a hole blocking layer, and an electron transport layer.

In addition, the organic material layer may use a variety of polymer materials to reduce the number of solvent processes (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer) rather than deposition. Can be prepared in layers.

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the material used. The compound according to the present invention can also act on a principle similar to that applied to an organic light emitting device in organic electronic devices including organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, organic transistors, and the like.

Hereinafter, preferred embodiments are provided to help understanding of the present invention. However, the following examples are only provided to more easily understand the present invention, and the contents of the present invention are not limited thereby.

In addition, it is understood that the compounds in which the production method is not specifically disclosed in each example of the present invention are prepared by a conventional method in the art or by referring to the production method described in other examples.

Example 1) Preparation of 6- (4- (3- (diphenylamino) phenoxy) phenyl) -N, N-diphenylpyren-1-amine ( 1 )

 1) Preparation of 6-bromo-N, N-diphenylpyren-1-amine

In the reactor, 30.00g of 1,6-dibromopyrene and 15.51g of diphenyl amine, tris (dibenzylideneacetone) dipalladium (0) 7.02g, sodium tert-butoxide 28.03g and tris tert-butylphosphonium tetrafluoro borate 2.22 After adding g, 500 mL of toluene is added. The reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, after cooling to room temperature, 1000 mL of ethyl acetate is added. After taking the organic layer, 500 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 6-bromo-N, N-diphenylpyren-1-amine. (18.68 g, yield 50.0%) MS: [M] = 448.

2) Preparation of 6- (4-bromophenyl) -N, N-diphenylpyren-1-amine

To the reactor, 5.0 g of 4-bromophenylboronic acid, 12.28 g of 6-bromo-N, N-diphenylpyren-1-amine, and 2.28 g of tetrakis (triphenylphosphine) palladium (0) were added, and 200 mL of dimethylformamide was added. 60 mL of 2M-potassium carbonate aqueous solution was added dropwise to the reaction mixture. The reaction mixture was heated to 80 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 100 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 6- (4-bromophenyl) -N, N-diphenylpyren-1-amine. (6.66 g, yield 51.0%) MS: [M] = 524

3) Preparation of 3- (diphenylamino) phenol

To the reactor, 10.0 g of bromobenzene and 3.82 g of 3-aminophenol, tris (dibenzylidene acetone) dipalladium (0) 2.68 g, sodium tert-butoxide 10.71 g and tris tert-butylphosphonium tetrafluoro borate 0.85 g were added. Then, 100 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 200 mL of ethyl acetate was added. After taking the organic layer, 100 mL of purified water is added and washed. 3 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to obtain 3- (diphenylamino) phenol. (3.83 g, yield 46.0%) MS: [M] = 261.

4) Preparation of 6- (4- (3- (diphenylamino) phenoxy) phenyl) -N, N-diphenylpyren-1-amine ( 1 )

To the reactor, 6- (4-bromophenyl) -N, N-diphenylpyren-1-amine 10.0g, 3- (diphenylamino) phenol 5.48g sodium hydroxide 1.53g, copper (I) chloride 0.57g is added, and pyridine 30mL is added. . The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/4) to obtain 6- (4- (3- (diphenylamino) phenoxy) phenyl) -N, N-diphenylpyren-1-amine of Chemical Formula 1 . (10.21 g, yield 76.0%) MS: [M] = 705.

Example 2) Preparation of N- (4- (4- (phenanthren-9-yl (phenyl) amino) phenoxy) phenyl) -N, 5-diphenylpyren-1-amine ( 2 )

1) Preparation of N, 6-diphenylpyren-1-amine

30.00 g of 1-bromo-6-phenylpyrene and 8.60 g of aniline in the reactor, 7.08 g of tris (dibenzylideneacetone) dipalladium (0), 28.25g of sodium tert-butoxide and tris tert-butylphosphonium tetrafluoro borate After adding 2.24 g, 500 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, after cooling to room temperature, 1000 mL of ethyl acetate is added. After taking the organic layer, 500 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain N, 6-diphenylpyren-1-amine. (15.82 g, yield 51.0%) MS: [M] = 369.

2) Preparation of N- (4-bromophenyl) -N, 6-diphenylpyren-1-amine

To the reactor, 5.0 g of 4-bromophenylboronic acid, 10.12 g of N, 6-diphenylpyren-1-amine, and 2.28 g of tetrakis (triphenylphosphine) palladium (0) were added, and 200 mL of dimethylformamide was added. 60 mL of 2M-potassium carbonate aqueous solution was added dropwise to the reaction mixture. The reaction mixture was heated to 80 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 100 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain N- (4-bromophenyl) -N, 6-diphenylpyren-1-amine. (6.66 g, yield 51.0%) MS: [M] = 524

3) Preparation of 3- (phenylamino) phenol

To the reactor was added 10.0 g bromobenzene and 7.65 g 3-aminophenol, 5.37 g tris (dibenzylideneacetone) dipalladium (0), 21.42 g sodium tert-butoxide and 1.70 g tris tert-butylphosphonium tetrafluoro borate. Then, 200 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 200 mL of purified water is added and washed. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to obtain 3- (phenylamino) phenol. (5.23 g, yield 44.3%) MS: [M] = 185.

4) Preparation of 3- (phenanthren-9-yl (phenyl) amino) phenol

In the reactor, 5.0g of 9-bromophenanthrene and 3.96g of 3- (phenylamino) phenol, tris (dibenzylideneacetone) dipalladium (0) 1.64g, sodium tert-butoxide 6.54g and tris tert-butylphosphonium tetrafluoro After adding 0.52 g of borate, 100 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 200 mL of ethyl acetate was added. After taking the organic layer, 100 mL of purified water is added and washed. 3 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to obtain 3- (phenanthren-9-yl (phenyl) amino) phenol. (3.68 g, yield 52.3%) MS: [M] = 361.

5) Preparation of N- (4- (4- (phenanthren-9-yl (phenyl) amino) phenoxy) phenyl) -N, 5-diphenylpyren-1-amine ( 2 )

Reactor N- (4-bromophenyl) -N, 6-diphenylpyren-1-amine 10.0g, 3- (phenanthren-9-yl (phenyl) amino) phenol 7.58g sodium hydroxide 1.53g, copper (I) chloride 0.57g After adding, 30 mL of pyridine is added. The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to perform N- (4- (4- (phenanthren-9-yl (phenyl) amino) phenoxy) phenyl) -N, 5 in Chemical Formula 2 . -diphenylpyren-1-amine. (11.36 g, Yield 74.0%) MS: [M] = 805.

Example 3) Preparation of 6- (3- (phenanthren-9-yl (phenyl) amino) phenoxy) -N, N-diphenylpyren-1-amine ( 3 )

To the reactor, 6-bromo-N, N-diphenylpyren-1-amine 10.0g, 3- (phenanthren-9-yl (phenyl) amino) phenol 8.87g sodium hydroxide 1.78g, copper (I) chloride 0.66g, and then pyridine Add 30mL. The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to perform 6- (3- (phenanthren-9-yl (phenyl) amino) phenoxy) -N, N-diphenylpyren-1- of Chemical Formula 3 amine. (12.03 g, 74.0% yield) MS: [M] = 729.

Example 4) 4- (6- (4- (3- (9H-carbazol-9-yl) phenoxy) phenyl) pyren-1-yl) -N, N-bis (4-tert-butylphenyl) -aniline ( 4 ) Preparation

1) Preparation of 1,6-bis (4-bromophenyl) pyrene

To the reactor, 10.0 g of 4-bromophenylboronic acid, 9.86 g of 1,6-dibromopyrene, and 5.75 g of tetrakis (triphenylphosphine) palladium (0) were added, and 200 mL of dimethylformamide was added. 120 mL of a 2M-potassium carbonate aqueous solution was added dropwise to the reaction mixture. The reaction mixture was heated to 80 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 100 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 1,6-bis (4-bromophenyl) pyrene. (6.50 g, yield 51.0%) MS: [M] = 512.

2) Preparation of 4- (6- (4-bromophenyl) pyren-1-yl) -N, N-bis (4-tert-butylphenyl) aniline

Reactor 1,6-bis (4-bromophenyl) pyrene 10.0g and bis (4-tert-butylphenyl) amine 6.04g, tris (dibenzylideneacetone) dipalladium (0) 1.64g, sodium tert-butoxide 6.57g And tris tert-butylphosphonium tetrafluoro borate 0.52 g was added, followed by 200 mL of toluene. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 200 mL of purified water is added and washed. 3 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to give 4- (6- (4-bromophenyl) pyren-1-yl) -N, N-bis (4-tert-butylphenyl) aniline Get (6.82 g, yield 49.0%) MS: [M] = 713.

3) Preparation of 3- (9H-carbazol-9-yl) phenol

In the reactor, 10.0g of 2,2'-dibromobiphenyl and 3.85g of 3-aminophenol, tris (dibenzylideneacetone) dipalladium (0) 2.70g, sodium tert-butoxide 10.78g and tris tert-butylphosphonium tetrafluoro After adding 0.86 g of borate, 200 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 200 mL of purified water is added and washed. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to obtain 3- (9H-carbazol-9-yl) phenol. (4.35 g, yield 52.3%) MS: [M] = 259.

4) 4- (6- (4- (3- (9H-carbazol-9-yl) phenoxy) phenyl) pyren-1-yl) -N, N-bis (4-tert-butylphenyl) -aniline ( 4 ) Manufacturing

Reactor 4- (6- (4-bromophenyl) pyren-1-yl) -N, N-bis (4-tert-butylphenyl) aniline 10.0g, 3- (9H-carbazol-9-yl) phenol 4.00g sodium After adding 1.12 g of hydroxide and 0.42 g of copper (I) chloride, 30 mL of pyridine is added. The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to obtain 4- (6- (4- (3- (9H-carbazol-9-yl) phenoxy) phenyl) pyren-1 of Chemical Formula 4 . -yl) -N, N-bis (4-tert-butylphenyl) -aniline. (8.88 g, yield 71.0%) MS: [M] = 891.

Example 5) 5- (4- (6- (4- (bis (4-methoxyphenyl) amino) phenyl) pyren-1-yloxy) phenyl) -N, N-bis (4-meth-oxy-phenyl) pyridin Preparation of -3-amine ( 5 )

1) Preparation of 1-bromo-6- (4-bromophenyl) pyrene

To the reactor, 10.0 g of 4-bromophenylboronic acid, 19.72 g of 1,6-dibromopyrene, and 5.75 g of tetrakis (triphenylphosphine) palladium (0) were added, and 200 mL of dimethylformamide was added. 120 mL of a 2M-potassium carbonate aqueous solution was added dropwise to the reaction mixture. The reaction mixture was heated to 80 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 100 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 1-bromo-6- (4-bromophenyl) pyrene. (11.29 g, yield 52.0%) MS: [M] = 436.

2) Preparation of 4- (6-bromopyren-1-yl) -N, N-bis (4-methoxyphenyl) aniline

In the reactor, 10.0g of 1-bromo-6- (4-bromophenyl) pyrene and 5.78g of bis (4-methoxyphenyl) amine, tris (dibenzylideneacetone) dipalladium (0) 1.93g, sodium tert-butoxide 7.71g After adding 0.61 g of tris tert-butylphosphonium tetrafluoro borate, 200 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 200 mL of purified water is added and washed. 3 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to obtain 4- (6-bromopyren-1-yl) -N, N-bis (4-methoxyphenyl) aniline. (6.57 g, Yield 49.0%) MS: [M] = 585.

3) Preparation of 4- (5- (bis (4-methoxyphenyl) amino) pyridin-3-yl) phenol

In the reactor, 10.0 g of 1-bromo-4-methoxybenzene and 5.48 g of 4- (5-aminopyridin-3-yl) phenol, 2.25 g of tris (dibenzylideneacetone) dipalladium (0), 8.89 g of sodium tert-butoxide After adding 0.71 g of tris tert-butylphosphonium tetrafluoro borate, 200 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 200 mL of purified water is added and washed. 3 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue is subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to obtain 4- (5- (bis (4-methoxyphenyl) amino) pyridin-3-yl) phenol. (5.22 g, yield 49.0%) MS: [M] = 398.

4) 5- (4- (6- (4- (bis (4-methoxyphenyl) amino) phenyl) pyren-1-yloxy) phenyl) -N, N-bis (4-methoxy-phenyl) pyridin-3-amine ( 5 ) Preparation

Reactor 4- (6-bromopyren-1-yl) -N, N-bis (4-methoxyphenyl) aniline 10.0g, 4- (5- (bis (4-methoxyphenyl) amino) pyridin-3-yl) phenol 7.50 g sodium hydroxide 1.37g, copper (I) chloride 0.51g is added and 30mL of pyridine is added. The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (ethyl acetate / hexane = 1/6) to give 5- (4- (6- (4- (bis (4-methoxyphenyl) amino) phenyl) pyren-1-yloxy in Chemical Formula 5 ) phenyl) -N, N-bis (4-methoxyphenyl) -pyridin-3-amine. (11.27 g, yield 73.0%) MS: [M] = 902.

Example 6) Preparation of 6,6 '-(4,4'-oxybis (4,1-phenylene)) bis (N, N-diphenylpyren-1-amine) ( 6 )

To the reactor, 10.0-g of 6- (4-bromophenyl) -N, N-diphenylpyren-1-amine, 4.0g of sodium hydroxide, and 0.57g of copper (I) chloride were added and 30mL of pyridine was added. The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentration residue was purified by silica gel chromatography (ethyl acetate / hexane = 1/4) carried by 6, 6 'of the formula (6) - (4,4'-oxybis (4,1- phenylene)) bis (N, N-diphenylpyren -1-amine). (4.05 g, yield 47.0%) MS: [M] = 905.

Example 7) Preparation of 4-((3- (6-((4-fluorophenyl) (phenyl) amino) pyren-1-yloxy) phenyl) (phenyl) amino) -benzonitrile ( 7 )

1) Preparation of 6-bromo-N-phenylpyren-1-amine

In the reactor, 20.00g of 1,6-dibromopyrene and 5.69g of aniline, tris (dibenzylideneacetone) dipalladium (0) 4.68g, sodium tert-butoxide 18.68g and tris tert-butylphosphonium tetrafluoro borate 1.48g After adding, 500 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, after cooling to room temperature, 1000 mL of ethyl acetate is added. After taking the organic layer, 500 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 6-bromo-N-phenylpyren-1-amine. (10.55 g, yield 51.0%) MS: [M] = 372.

2) Preparation of 6-bromo-N- (4-fluorophenyl) -N-phenylpyren-1-amine

In the reactor, 5.00g of 1-bromo-4-fluorobenzene and 11.70g of 6-bromo-N-phenylpyren-1-amine, tris (dibenzylideneacetone) dipalladium (0) 2.41g, sodium tert-butoxide 9.61g and tris After tert-butylphosphonium tetrafluoro borate was added 0.76 g, toluene 300 mL was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 500 mL of ethyl acetate was added. After taking the organic layer, washed with 300 mL of purified water. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 6-bromo-N- (4-fluorophenyl) -N-phenylpyren-1-amine. (6.61 g, yield 49.6%) MS: [M] = 466.

3) Preparation of 4-((3-hydroxyphenyl) (phenyl) amino) benzonitrile

10.00 g of 4-bromobenzonitrile and 11.29 g of 6- (3-aminophenoxy) -N- (4-fluorophenyl) -N-phenylpyren-1-amine in the reactor, tris (dibenzylideneacetone) dipalladium (0) 4.63g, sodium 18.48 g of tert-butoxide and 1.47 g of tris tert-butylphosphonium tetrafluoro borate were added, followed by 300 mL of toluene. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 500 mL of ethyl acetate was added. After taking the organic layer, washed with 300 mL of purified water. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 4-((3-hydroxyphenyl) (phenyl) amino) benzonitrile. (7.71 g, yield 49.0%) MS: [M] = 286.

4) Preparation of 4-((3- (6-((4-fluorophenyl) (phenyl) amino) pyren-1-yloxy) phenyl) (phenyl) amino) benzonitrile ( 7 )

Reactor 6-bromo-N- (4-fluorophenyl) -N-phenylpyren-1-amine 10.0g, 4-((3-hydroxyphenyl) (phenyl) amino) benzonitrile 6.75g sodium hydroxide 1.72g, copper (I) chloride After adding 0.64g, 30mL of pyridine is added. The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 4-((3- (6-((4-fluorophenyl) (phenyl) amino) pyren-1-yloxy) phenyl of Chemical Formula 7 ) (phenyl) amino) benzonitrile. (10.85 g, yield 75.3%) MS: [M] = 672.

Example 8) Preparation of 6- (3- (diphenylamino) phenoxy) -N- (3- (3- (diphenylamino) phenoxy) phenyl) -N-phenyl-pyren-1-amine ( 8 )

1) Preparation of 6-bromo-N-phenylpyren-1-amine

In the reactor 1,6-dibromopyrene 10.00g and aniline 2.85g, tris (dibenzylideneacetone) dipalladium (0) 2.34g, sodium tert-butoxide 9.34g and tris tert-butylphosphonium tetrafluoro borate 0.74g After adding, 300 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 500 mL of ethyl acetate was added. After taking the organic layer, washed with 300 mL of purified water. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 6-bromo-N-phenylpyren-1-amine. (4.55 g, yield 44.0%) MS: [M] = 372.

2) Preparation of 6-bromo-N- (4-bromophenyl) -N-phenylpyren-1-amine

In the reactor 1,4-dibromobenzene 10.00g and 6-bromo-N-phenylpyren-1-amine 17.36g, tris (dibenzylideneacetone) dipalladium (0) 3.57g, sodium tert-butoxide 14.26g and tris tert- After adding 1.13 g of butylphosphonium tetrafluoro borate, 300 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. After the reaction was completed, after cooling to room temperature, 500 mL of ethyl acetate was added. After taking the organic layer, washed with 300 mL of purified water. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 6-bromo-N- (4-bromophenyl) -N-phenylpyren-1-amine. (9.16 g, yield 41.0%) MS: [M] = 527.

3) Preparation of 6- (3- (diphenylamino) phenoxy) -N- (3- (3- (diphenylamino) phenoxy) phenyl) -N-phenylpyren-1-amine ( 8 )

To the reactor, 10.0 g of 6-bromo-N- (4-bromophenyl) -N-phenylpyren-1-amine, 5.45 g of 3- (diphenylamino) phenol, 1.52 g of sodium hydroxide, and 0.56 g of copper (I) chloride were added and 30 mL of pyridine was added. Input. The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to perform 6- (3- (diphenylamino) phenoxy) -N- (3- (3- (diphenylamino) phenoxy) phenyl) of Chemical Formula 1- Obtain N-phenylpyren-1-amine. (12.14 g, yield 72.1%) MS: [M] = 888.

Example 9) Preparation of N, N '-(4,4'-oxybis (4,1-phenylene)) bis (N, 7-diphenylpyren-2-amine) ( 9 )

1) Preparation of 2-bromo-7-phenylpyrene

To the reactor, 5.0 g of phenylboronic acid, 16.24 g of 2,7-dibromopyrene and 4.74 g of tetrakis (triphenylphosphine) palladium (0) were added, and 200 mL of dimethylformamide was added. 100 mL of 2M-potassium carbonate aqueous solution was added dropwise to the reaction mixture. The reaction mixture was heated to 80 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 400 mL of ethyl acetate was added. After taking the organic layer, 100 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain 2-bromo-7-phenylpyrene. (6.01 g, yield 41.0%) MS: [M] = 357.

2) Preparation of N, 7-diphenylpyren-2-amine

20.00 g of 2-bromo-7-phenylpyrene and 5.74 g of aniline, 4.72 g of tris (dibenzylideneacetone) dipalladium (0), 18.83g of sodium tert-butoxide and tris tert-butylphosphonium tetrafluoro borate After adding 1.49 g, 500 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, after cooling to room temperature, 1000 mL of ethyl acetate is added. After taking the organic layer, 500 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain N, 7-diphenylpyren-2-amine. (10.76 g, yield 52.0%) MS: [M] = 369.

3) Preparation of N- (4-bromophenyl) -N, 7-diphenylpyren-2-amine

In the reactor, 5.00g of 1,4-dibromobenzene and 8.61g of N, 7-diphenylpyren-2-amine, tris (dibenzylideneacetone) dipalladium (0) 1.79g, sodium tert-butoxide 7.13g and tris tert-butylphosphine After adding 0.57 g of ponium tetrafluoro borate, 500 mL of toluene was added. The reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, after cooling to room temperature, 1000 mL of ethyl acetate is added. After taking the organic layer, 500 mL of purified water is added and washed. 10 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to obtain N- (4-bromophenyl) -N, 7-diphenylpyren-2-amine. (5.11 g, yield 46.0%) MS: [M] = 524.

4) Preparation of N, N '-(4,4'-oxybis (4,1-phenylene)) bis (N, 7-diphenylpyren-2-amine) ( 9 )

After adding 10.0 g of N- (4-bromophenyl) -N, 7-diphenylpyren-2-amine, 4.0 g of sodium hydroxide, and 0.57 g of copper (I) chloride, 30 mL of pyridine is added to the reactor. The reaction mixture is heated to 120 ° C. and stirred. After the reaction was completed, after cooling to room temperature, 40 mL of ethyl acetate was added. After taking the organic layer, washing with 40 mL of purified water was repeated 3 times. 5 g of anhydrous magnesium sulfate was added to the organic layer, followed by stirring for 30 minutes. The organic layer is filtered and concentrated under reduced pressure. The concentration residue was purified by silica gel chromatography (ethyl acetate / hexane = 1/4) of the formula (9) subjected to N, N '- (4,4'- oxybis (4,1-phenylene)) bis (N, 7-diphenylpyren -2-amine). (4.05 g, yield 47.0%) MS: [M] = 905.

Comparative Example (TPPDA)

(J. Org. Chem., 2009, 74, 8472)

<Experimental Example>

Experimental Examples 1 to 9 and Comparative Experimental Examples

A glass substrate coated with a thin film coated with ITO at a thickness of 1500 에 was placed in secondary distilled water in which Fischer's detergent was dissolved and washed with ultrasonic waves for 30 minutes. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 2 minutes with distilled water twice. After washing with distilled water, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, and methanol was performed, followed by drying, and then transferred to a plasma cleaner, followed by washing the substrate for 5 minutes using oxygen plasma and then transferred to a vacuum evaporator.

After the 2-TNATA 500Å vacuum deposition as a hole injection layer on the prepared ITO transparent electrode, the NPB 300Å vacuum deposition as a hole transport layer, and the dopant and host were laminated with the material of the example and ADN as shown in Table 1 below. The compounds of the Examples and Comparative Examples were doped by 5% to vacuum-deposit to a thickness of 300, and the TPBi compounds were vacuum-deposited to a thickness of 400 정 as a hole blocking layer and a hole transport layer, and sequentially deposited with LiF 5 Li and Al (aluminum) 2000Å. A cathode was formed. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, lithium fluoride was maintained at 0.2 Å / sec, and aluminum was maintained at a deposition rate of 3 to 7 Å / sec.

Table 1 shows electroluminescence characteristics of the organic light-emitting device manufactured above.

Experimental example Host Dopant Current density
(mA / cm ₂ ) color efficiency
(cd / A) life span
(hrs) Comparative Experimental Example ADN TPPDA 10 blue 6.2 5,300 One ADN Example 1 10 blue 11.9 9,500 2 ADN Example 2 10 blue 11.1 11,600 3 ADN Example 3 10 blue 10.8 10,200 4 ADN Example 4 10 blue 11.9 11,800 5 ADN Example 5 10 blue 11.7 10,300 6 ADN Example 6 10 blue 11.5 10,500 7 ADN Example 7 10 blue 9.1 8,400 8 ADN Example 8 10 blue 11.7 11,200 9 ADN Example 9 10 blue 11.3 11,500

From the results of Table 1, it was confirmed that the compound for an organic electroluminescent device according to the present invention has improved luminous efficiency and lifetime characteristics.

The organic electronic device using the compound for an organic electroluminescent device of the present invention has high luminous efficiency and lifetime, and blue light emission is obtained. For this reason, it is useful industrially as an organic light emitting element with high practicality.

The organic electronic device of the present invention can be suitably used for a flat panel display, a flat light emitter, a light emitting body of a surface-emitting organic light emitting device for lighting, a flexible light emitter, a copier, a printer, a light source such as an LCD backlight or a meter, a display panel, a marker, or the like. .

Claims (8)

Compound for an organic electroluminescent device represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
Ar ₁ to Ar ₃ are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, and X is a substituted or unsubstituted pyrene (pyrene) ) Group, R ₁ to R ₄ are each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted carbon atom number 7 An amino group substituted with an aryl group of 40 to 40, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, R ₁ and R ₂ or R ₃ and R ₄ may be fused to each other to form a substituted or unsubstituted ring.
L ₁ , and L ₂ are integers of 0 or 3, m ₁ is an integer of 0 to 2 , m ₂ is an integer of 1 or 2, and m ₁ + m ₂ ≥ 1.
At this time, when m ₁ is 0, Ar ₁ ′ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms,
When m ₁ is 1, Ar ₁ ′ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms,
When m ₁ is 2, Ar ₁ ′ is a substituted or unsubstituted trivalent arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted trivalent heterocyclic group having 5 to 40 carbon atoms,
At this time, when m ₂ is 1, Y ₂ is a simple bond, or -N (R ')-Ar "-(wherein, Ar" is each independently of each other independently substituted or unsubstituted 6 to 40 carbon atoms. Is an arylene group, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, R 'is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted complex having 5 to 40 carbon atoms An amino group substituted with a vented, substituted or unsubstituted aryl group having 7 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms) ,
When m ₂ is 2, Y ₂ is -N (R ')-Ar "-(where Ar" is each independently independently of each other, a substituted or unsubstituted trivalent arylene group having 6 to 40 carbon atoms, Substituted or unsubstituted trivalent heterocyclic group having 5 to 40 carbon atoms, R 'is substituted or unsubstituted aryl group having 6 to 40 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, substituted or An amino group substituted with an unsubstituted aryl group having 7 to 40 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms)
Y ₁ is a simple bond, -Ar'- or -Ar'-O- (Ar 'is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent complex having 5 to 40 carbon atoms. Ventilation, R 'is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted amino group having 7 to 40 carbon atoms aryl group , Substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms). According to claim 1,
The compound for an organic electroluminescent device is a compound for an organic electroluminescent device represented by the following Chemical Formula 2 or Chemical Formula 3:
[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,
Ar ₁ to Ar ₆ , and Ar ₈ are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, and L ₁ , L ₂ , L ₃ and L ₄ are integers from 0 to 3. R ₁ to R ₉ are each independently of each other a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted aryl having 7 to 40 carbon atoms. An amino group substituted with a group, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms, R ₁ and R ₂ or R ₃ and R ₄ and R ₅ And R ₆ or R ₈ and R ₉ may be fused to each other to form a substituted or unsubstituted ring. X is a substituted or unsubstituted Pyrene group. n ₁ is an integer of 0 or 1, n ₂ is an integer of ₁ , and n ₁ + n ₂ ≥ 1.
At this time, when n ₁ is 0, Ar ₅ ′ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms,
When n ₁ is 1, Ar ₅ ′ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms,
When n ₂ is 1, Ar ₇ is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms. According to claim 1,
The compound for an organic electroluminescent device is a compound for an organic electroluminescent device represented by the following formula (4):
[Formula 4]

In Chemical Formula 4,
Ar ₉ and Ar ₁₀ are each independently a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 40 carbon atoms, and L ₅ is 0 to 3 It is an integer. R ₁₀ to R ₁₃ are each independently of each other a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted aryl having 7 to 40 carbon atoms. An amino group substituted with a group, a substituted or unsubstituted arylalkyl group having 7 to 40 carbon atoms, or a substituted or unsubstituted aryloxyl group having 6 to 40 carbon atoms, and R ₁₀ and R ₁₁ or R ₁₂ and R ₁₃ are fused to each other To form a substituted or unsubstituted ring. X is a substituted or unsubstituted Pyrene group. According to claim 1,
The Ar ₁ , Ar ₂ , Ar ₃ , Ar 'and Ar "are each independently an organic electroluminescent device compound selected from the following formula.

In the above, Z and Y may be the same or different from each other, a hydrogen atom, a cyan atom, a halogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted Or an unsubstituted aralkyl group having 7 to 40 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 40 carbon atoms, a substituted or unsubstituted aralkylthio group having 7 to 40 carbon atoms, a substituted or unsubstituted carbon Aryl group having 6 to 40 atoms, substituted or unsubstituted heterocyclic group having 5 to 40 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, substituted or unsubstituted aryl having 6 to 40 carbon atoms It is a thio, substituted or unsubstituted aminoaryl group having 6 to 40 carbon atoms, an amino group, a cyano group, a silyl group, or a phosphine oxide group. According to claim 1,
The compound for an organic electroluminescent device is represented by the following formulas 5 to 13:
[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

. An organic electronic device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the electrodes,
At least one layer of the organic material layer is an organic electronic device comprising the compound for an organic electroluminescent device of any one of claims 1 to 4. The method of claim 6,
The organic layer has a hole injection layer, a hole transport layer, a function layer having a hole injection function and a hole transport function simultaneously, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron transport function and an electron injection function simultaneously An organic electronic device comprising at least one of a functional layer. The method of claim 6,
The organic electronic device is an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-Paper), an organic photoreceptor (OPC) or an organic transistor (OTFT), characterized in that the organic electronic device.