JP2009161468A - Aromatic amine derivative and organic electroluminescent device using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent element having a long life and a high light-emitting efficiency, and an aromatic amine derivative for achieving the same. <P>SOLUTION: This aromatic amine derivative obtained by substituting both amino groups in a diaminochrysene derivative with a 4-(2-phenylpropan-2-yl)phenyl group and an aryl group is provided. Also, the organic electroluminescent element in which an organic thin film layer consisting of one layer or a plurality of layers containing at least a light-emitting layer is nipped/held between an anode and a cathode is provided with that at least one layer of the organic thin film layers contains the aromatic amine derivative singly or as a component of a mixture. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to an aromatic amine derivative and an organic electroluminescence (EL) device using the same, and in particular, an organic electroluminescence device having excellent blue chromaticity, a long lifetime, and high luminous efficiency, and an aromatic amine derivative that realizes the organic electroluminescence device. It is about.

An organic EL element using an organic substance is considered to be promising for use as an inexpensive large-area full-color display element of a solid light emitting type, and many developments have been made. In general, an EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Furthermore, this is a phenomenon in which electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
Conventional organic EL elements have a higher driving voltage and lower light emission luminance and light emission efficiency than inorganic light-emitting diodes. Further, the characteristic deterioration has been remarkably not put into practical use. Although recent organic EL devices have been gradually improved, higher light emission efficiency and longer life are required.
For example, a technique using a single monoanthracene compound as an organic light emitting material is disclosed (Patent Document 1). However, in this technique, for example, at a current density of 165 mA / cm ² , only a luminance of 1650 cd / m ² is obtained, and the efficiency is 1 cd / A, which is extremely low and not practical. In addition, a technique using a single bisanthracene compound as an organic light emitting material is disclosed (Patent Document 2). However, even in this technique, the efficiency is as low as about 1 to 3 cd / A, and improvement for practical use has been demanded. On the other hand, a long-life organic EL element using a distyryl compound as an organic light-emitting material and styrylamine added thereto has been proposed (Patent Document 3). However, this element does not have a sufficient lifetime, and further improvement has been demanded.
Patent Document 4 describes an organic EL element material substituted with a substituent having a benzene ring at each end. However, since this organic EL element material has a high vapor deposition temperature, the material is decomposed during element fabrication.
Patent Document 5 discloses an aromatic amine derivative having a 4- (2-phenylpropan-2-yl) phenyl group. However, further improvements have been demanded for organic EL devices using these.

Japanese Patent Laid-Open No. 11-3782 JP-A-8-12600 International Publication WO94 / 006157 JP-A-10-251633 International Publication WO2007 / 100096

  The present invention has been made to solve the above-described problems, and an object of the present invention is to provide an organic EL device having a long lifetime and high luminous efficiency, and an aromatic amine derivative that realizes the organic EL device.

  As a result of intensive studies to develop an aromatic amine derivative having the above-mentioned preferable properties and an organic EL device using the same, the present inventors have found that both amino groups are 4- (2-phenylpropane) in the diaminochrysene derivative. It has been found that when an aromatic amine derivative substituted with a 2-yl) phenyl group and other substituents is used as a light-emitting material, high luminous efficiency and long life are obtained. The present invention has been completed based on such findings.

That is, the present invention provides an aromatic amine derivative represented by the following general formula (1).

[Wherein Ar ₀ represents a substituted or unsubstituted chrysenylene group. Ar ₁ and Ar ₃ are each a 4- (2-phenylpropan-2-yl) phenyl group represented by the following general formula (2).

Ar ₂ and Ar ₄ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms. Ar ₂ and Ar ₄ may be the same or different. ]

  Further, the present invention provides an organic EL device in which an organic thin film layer comprising at least one light emitting layer or a plurality of light emitting layers is sandwiched between a cathode and an anode, wherein at least one layer of the organic thin film layer contains the aromatic amine derivative. The present invention provides an organic EL device contained alone or as a component of a mixture.

  The organic EL device using the aromatic amine derivative of the present invention has a high luminous efficiency, is difficult to deteriorate even after long-time use, and has a long life.

The aromatic amine derivative of the present invention is a compound represented by the following general formula (1).

In the general formula (1), Ar ₀ is a substituted or unsubstituted chrysenylene group, and 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 1,11-, 1,12-, 2,3-, 2,4-, 2,5-, 2,6-, 2,8-, 2,9-, 2,10-, 2,11-, 2,12-, 3,4-, 3,5-, 3,6-, 3,9-, 3, 10-, 3,11-, 3,12-, 4,5-, 4,6-, 4,10-, 4,11-, 4,12-, 5,6-, 5,11-, 5,12-, and 6,12- Selected from the following: In particular, a substituted or unsubstituted 2,8-chrysenylene group and an unsubstituted 6,12-chrysenylene group are preferable.

In the general formula (1), Ar ₁ and Ar ₃ are each a 4- (2-phenylpropan-2-yl) phenyl group represented by the following general formula (2).

In the general formula (1), Ar ₂ and Ar ₄ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms. Ar ₂ and Ar ₄ may be the same or different.
An aromatic amine derivative in which all of Ar _{1 to} Ar ₄ in the general formula (1) are 4- (2-phenylpropan-2-yl) phenyl groups represented by the general formula (2) is preferable.

In the general formula (1), examples of the substituent for Ar ₀ , Ar ₂ and Ar ₄ include a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted nucleus Aryloxy group having 6 to 50 carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, amino group, halogen atom, cyano group, nitro Group, hydroxyl group, carboxyl group and the like.
In addition, the number of carbon atoms and the number of atoms of each group in each of the above general formulas are numbers not including those of the substituent. Moreover, the carbon number of an aralkyl group is the carbon number of an aryl part.

Examples of the aryl group include a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, 4 -Cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group, chrysenyl group, fluoranthenyl group, perylenyl group and the like can be mentioned.
Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, stearyl, and 2-phenyl. Isopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α, α-ditrifluoromethylbenzyl group, triphenyl Examples thereof include a methyl group and an α-benzyloxybenzyl group.

Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a bicycloheptyl group, a bicyclooctyl group, a tricycloheptyl group, and an adamantyl group. And a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a bicycloheptyl group, a bicyclooctyl group, and an adamantyl group are preferable.
Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, various pentyloxy groups, and various hexyloxy groups.

  Examples of the aralkyl group include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α -Naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o Bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl Group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2- A phenyl isopropyl group, a 1-chloro-2-phenyl isopropyl group, etc. are mentioned.

The aryloxy group and the arylthio group are represented as -OY and -SY, respectively. Examples of Y include the same examples as the aryl group.
The alkoxycarbonyl group is represented by —COOZ, and examples of Z include the same examples as the alkyl group.

In the general formula (1), as substituents for Ar ₀ , Ar ₂ and Ar ₄ , among them, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an alkoxy having 1 to 10 carbon atoms Group, preferably an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 5 to 7 carbon atoms, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, A tert-butyl group, n-pentyl group, n-hexyl group, cyclopentyl group, and cyclohexyl group are particularly preferred.

Specific examples of the aromatic amine derivative represented by the general formula (1) of the present invention are shown below, but are not limited to these exemplified compounds. Me is a methyl group.

Next, the manufacturing method of the aromatic amine derivative of this invention is demonstrated.
The method for producing the aromatic amine derivative represented by the general formula (1) of the present invention is not particularly limited and may be produced by a known method. Room. Chim. , 34 1907 (1989) (MD Bancia et al.), 2,8-dibromochrysene obtained by the method described in the above, is aminated with a diarylamine to produce an aromatic amine derivative.

The aromatic amine derivative of the present invention is suitable as a material for an organic EL device, particularly preferably a light emitting material, and suitably used as a blue light emitting material.
Moreover, the aromatic amine derivative of the present invention is also suitable as a doping material for organic EL devices.

In the organic EL device of the present invention, an organic thin film layer comprising at least one light emitting layer or a plurality of layers is sandwiched between a cathode and an anode, and at least one layer of the organic thin film layer contains the aromatic amine derivative alone or as a mixture. It is contained as a component. In the organic EL device of the present invention, the aromatic amine derivative is preferably such that all of Ar _{1 to} Ar ₄ in the general formula (1) are 4- (2-phenylpropan-2-yl) phenyl groups.
When the organic EL device of the present invention is a single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and may further contain a hole injecting material or an electron injecting material in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material. The aromatic amine derivative of the present invention has high emission characteristics and has excellent hole injection properties, hole transport properties, electron injection properties, and electron transport properties. Can be used.
In the organic EL device of the present invention, the light emitting layer preferably contains the aromatic amine derivative of the present invention, the content is usually 0.1 to 20% by weight, and more preferably 1 to 10% by weight. Further, the aromatic amine derivative of the present invention has extremely high fluorescence quantum efficiency, high hole transport ability and electron transport ability, and can form a uniform thin film. Therefore, the light emitting layer can be formed only with this aromatic amine derivative. It is also possible to form.
Further, the organic EL device of the present invention is an organic EL device in which an organic thin film layer composed of at least two layers including at least a light emitting layer is sandwiched between a cathode and an anode. It is also preferable to have an organic layer mainly composed of an aromatic amine derivative. Examples of the organic layer include a hole injection layer and a hole transport layer.
The content of the aromatic amine derivative in the light emitting layer is preferably 0.01 to 20% by weight, more preferably 0.5 to 20% by weight, still more preferably 1 to 20% by weight, and particularly preferably 5 to 5% by weight. 20% by weight.

  When the aromatic amine derivative of the present invention is used as a light emitting material for an organic EL device, the light emitting layer is composed of at least one aromatic amine derivative and a compound represented by the following formulas (i) and (ii). It is preferable to include at least one selected, and it is more preferable that at least one selected from the compounds represented by the following formulas (i) and (ii) is a host material.

で表される。 Formula (i) is

It is represented by

In formula (i), A ₁ and A ₂ are each independently a group derived from a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms. The aromatic ring may be substituted with one or more substituents. The aromatic ring has a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms. Group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group (the aryl portion has 6 to 50 carbon atoms, the alkyl portion has 1 to 5 carbon atoms), substituted or unsubstituted carbon number 6-50 aryloxy groups, substituted or unsubstituted arylthio groups having 6 to 50 carbon atoms, substituted or unsubstituted alkoxycarbonyl groups (the alkoxy moiety has 1 to 50 carbon atoms), substituted or unsubstituted silyl groups, carboxyls The group is selected from a group, a halogen atom, a cyano group, a nitro group and a hydroxyl group, and selected from the groups described below as specific examples of R _{1 to} R ₈ . When the aromatic ring is substituted with two or more substituents, the substituents may be the same or different, and adjacent substituents are bonded to each other to form a saturated or unsaturated cyclic structure. It may be formed. A ₁ and A ₂ are preferably different. Further, at least one of A ₁ and A ₂ is preferably a substituent having a substituted or unsubstituted condensed ring group having 10 to 30 carbon atoms, and is a substituent having a substituted or unsubstituted naphthyl group. Is more preferable.

Examples of the group derived from a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms of A ₁ and A ₂ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, and a 2-anthryl group. 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p -Terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-triphenyl group Group, p-tolyl group, p-t-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1 -Anthryl group, 4'-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, etc., preferably substituted or unsubstituted aromatic having 10 to 14 nuclear carbon atoms. A group derived from a ring, particularly preferably a 1-naphthyl group, a 2-naphthyl group, or a 9-phenanthryl group.

R _{1 to} R ₈ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms, a substituted or unsubstituted carbon number. An alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group (the aryl moiety has 6 carbon atoms) To 50, the alkyl moiety has 1 to 50 carbon atoms), a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group (Alkyl moiety has 1 to 50 carbon atoms), substituted or unsubstituted silyl group, carboxyl group, halogen atom, cyano group, nitro group and hydroxyl Selected from the group consisting of.

Examples of the substituted or unsubstituted aryl group having 6 to 50 carbon atoms of R _{1 to} R ₈ in formula (i) include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p- Terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-triphenyl Group, p-tolyl group, p-t-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1- Anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group and the like can be mentioned.

Examples of the substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms of R _{1 to} R ₈ in formula (i) include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, and 2-pyridinyl group. 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, quinolyl group, 3-quinolyl group, 4 -Quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7 -Isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1 -Phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthate Dinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthroline-3-yl group, 1,7-phenanthroline-4-yl group, 1,7-phenanthroline-5 -Yl group, 1,7-phenanthroline-6-yl group, 1,7-phenanthroline-8-yl group, 1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10-yl group, 1, 8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group, 1,8-phenanthroline-4-yl group, 1,8-phenanthroline-5- Yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8-phenanthroline-10-yl group, 1,9 -Phenanthrolin-2-yl group, 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-yl group, 1,9-phenanthroline-5-yl group, 1,9-phenanthroline-6-yl Group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-2-yl group, 1,10- Phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group, 2,9-phenanthroline-1-yl group, , 9-phenanthroline-3-yl group, 2,9-phenanthroline-4-yl group, 2,9-phenanthroline-5-yl group, 2,9-phenanthroline-6-yl group, 2,9-phenanthroline-7 -Yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-yl group, 2,8-phenanthroline-1-yl group, 2,8-phenanthroline-3-yl group, 2, 8-phenanthroline-4-yl group, 2,8-phenanthroline-5-yl group, 2,8-phenanthroline-6-yl group, 2,8-phenanthroline-7-yl group, 2,8-phenanthroline-9- Yl group, 2,8-phenanthroline-10-yl group, 2,7-phenanthroline-1-yl group, 2,7-phenanthroline-3-yl group, 2,7-phenane Lorin-4-yl group, 2,7-phenanthroline-5-yl group, 2,7-phenanthroline-6-yl group, 2,7-phenanthroline-8-yl group, 2,7-phenanthroline-9-yl group 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group Group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group Group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylphenyl Roll-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methyl Pyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrole-1 -Yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, Examples include 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group, 4-t-butyl 3-indolyl group, and the like.

Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R _{1 to} R ₈ in formula (i) include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, and an isobutyl group. Group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1 , 2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3 Trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3- Diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1, 3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl Group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group Nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2 , 3-trinitropropyl group and the like.

Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms of R _{1 to} R ₈ and the aromatic ring substituent in formula (i) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, 4 -Methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like can be mentioned.

The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R _{1 to} R ₈ in formula (i) is a group represented by —OY, and Y is the substituted or unsubstituted group of R ^{5 to} R ¹² . It is selected from alkyl groups having 1 to 50 carbon atoms.

The substituted or unsubstituted aralkyl group (the aryl part has 6 to 50 carbon atoms and the alkyl part has 1 to 50 carbon atoms) as a substituent of R _{1 to} R ₈ in formula (i) includes a benzyl group, 1-phenylethyl Group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1 -Α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthyl Isopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p- Lorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group P-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o -Nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like.

The substituted or unsubstituted aryloxy group and arylthio group having 6 to 50 atoms of R _{1 to} R ₈ in formula (i) are represented as —OY ′ and —SY ″, respectively. R ^{5 to} R ¹² are selected from substituted or unsubstituted aryl groups having 6 to 50 atoms.

The substituted or unsubstituted alkoxycarbonyl group of R _{1 to} R ₈ in formula (i) (wherein the alkyl moiety has 1 to 50 carbon atoms) is represented as —COOZ, and Z represents the substituted or unsubstituted R ^{5 to} R ¹² described above. Selected from alkyl groups having 1 to 50 carbon atoms.

Examples of the substituted silyl group of R _{1 to} R ₈ in the formula (i) include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triphenylsilyl group.

Examples of the halogen atom of R _{1 to} R ₈ in the formula (i) include fluorine, chlorine, bromine, iodine and the like.
R _{1 to} R ₈ and / or the substituent of the aromatic ring of A ₁ and A ₂ are a halogen atom, hydroxyl group, nitro group, cyano group, alkyl group, aryl group, cycloalkyl group, alkoxy group, aromatic Further substituted with an aromatic group, aralkyl group, aryloxy group, arylthio group, alkoxycarbonyl group, carboxyl group or the like.

（式（i'）中、Ａ₁、Ａ₂およびＲ₁〜Ｒ₈は、式（i）で定義したとおりである。ただし、アントラセン構造の９位及び１０位の置換基Ａ₁とＡ₂は、Ｘ−Ｙ軸に対して非対称である。） The anthracene derivative represented by the formula (i) is preferably a compound having a structure represented by the following formula (i ′).

(In the formula (i ′), A ₁ , A ₂ and R _{1 to} R ₈ are as defined in the formula (i), provided that the substituents A ₁ and A _{2 at} the 9th and 10th positions of the anthracene structure are as follows. Is asymmetric with respect to the XY axis.)

  Specific examples of the anthracene derivative represented by the formula (i) used in the organic EL device of the present invention include an anthracene skeleton in the molecule shown in JP-A-2004-356033 [0043] to [0063]. Well-known various anthracene derivatives such as compounds having two or compounds having one anthracene skeleton shown in pages 27 to 28 of WO 2005/061656 can be mentioned. A typical example is shown below.

(In the formula, Ar ₅ and Ar ₆ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms.
L ₁ and L ₂ are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group.
s is an integer of 0 to 2, p is an integer of 1 to 4, q is an integer of 0 to 2, and r is an integer of 0 to 4.
L ₁ or Ar ₅ is bonded to any one of positions 1 to ₅ of pyrene, and L ₂ or Ar ₆ is bonded to any of positions 6 to 10 of pyrene.
However, when p + r is an even number, Ar ₅ , Ar ₆ , L ₁ and L ₂ satisfy the following (1) or (2).
(1) Ar ₅ ≠ Ar ₆ and / or L ₁ ≠ L ₂ (where ≠ indicates a group having a different structure)
(2) When Ar ₅ = Ar ₆ and L ₁ = L ₂
(2-1) s ≠ q and / or p ≠ r, or
(2-2) When s = q and p = r,
(2-2-1) L ₁ and L ₂ or pyrene are bonded to different bonding positions on Ar ₅ and Ar ₆ , respectively. (2-2-2) L ₁ and L ₂ or pyrene is bonded If it is bonded to the same position of Ar ₅ and Ar _6, when the substitution position of pyrene L ₁ and L ₂ or Ar ₅ and Ar ₆ are 1- and 6-position, or 2- and 7-position There is no. )
Specific examples and substituents of the groups Ar ₅ and Ar ₆ and L ₁ and L ₂ are the same as those described in the general formula (1).

  Specific examples of the pyrene derivative of the general formula (ii) are shown below, but are not limited to these exemplified compounds.

In addition, the number of carbon atoms and the number of atoms of each group in the general formulas (i) and (ii) are those not including those of the substituent. Moreover, the carbon number of an aralkyl group is the carbon number of an aryl part.
In the “substituted or unsubstituted... Group” of the above general formulas, an arbitrary substituent is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted carbon group having 1 to 50 carbon atoms. Alkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, substituted Or an unsubstituted arylthio group having 6 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, and the like. .

In the present invention, organic EL elements having a plurality of organic thin film layers are (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole). (Injection layer / light emitting layer / electron injection layer / cathode) and the like.
In addition to the aromatic amine derivative of the present invention, further known light emitting materials, doping materials, hole injecting materials, and electron injecting materials can be used for the plurality of layers as needed. The organic EL element can prevent the brightness | luminance and lifetime fall by quenching by making the said organic thin film layer into a multilayer structure. If necessary, a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination. Further, by using a doping material, it is possible to improve light emission luminance and light emission efficiency and to obtain red and blue light emission. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed with a layer configuration of two or more layers. In that case, in the case of a hole injection layer, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call. Similarly, in the case of an electron injection layer, a layer that injects electrons from an electrode is referred to as an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.

  Examples of the host material or doping material other than the general formula (1) that can be used in the light emitting layer together with the aromatic amine derivative of the present invention include naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene. , Tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthracenyl) benzene, etc. Condensed polyaromatic compounds and their derivatives, organometallic complexes such as tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4- (phenylphenolinato) aluminum, triarylamido Derivatives, styrylamine derivatives, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, diketopyrrolopyrrole derivatives, acridone derivatives, quinacridone Examples thereof include, but are not limited to, derivatives.

  As a hole injection material, it has the ability to transport holes, has a hole injection effect from the anode, an excellent hole injection effect for the light emitting layer or light emitting material, and excitons generated in the light emitting layer. A compound that prevents movement to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acyl hydrazone, polyaryl Examples include alkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and derivatives thereof, and polymer materials such as polyvinyl carbazole, polysilane, and conductive polymer. However, it is not limited to these.

Among the hole injection materials that can be used in the organic EL device of the present invention, more effective hole injection materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
Examples of the aromatic tertiary amine derivative include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4. '-Diamine, N, N, N', N '-(4-methylphenyl) -1,1'-phenyl-4,4'-diamine, N, N, N', N '-(4-methylphenyl) ) -1,1′-biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-( Methylphenyl) -N, N ′-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, etc. Or oligomers having these aromatic tertiary amine skeletons Or is a polymer, but is not limited thereto.

Examples of the phthalocyanine (Pc) derivatives include H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO) AlPc, (HO) GaPc, VOPc, and OPP Although there exist phthalocyanine derivatives and naphthalocyanine derivatives, such as MoOPc and GaPc-O-GaPc, it is not limited to these.
Further, the organic EL device of the present invention includes a layer containing these aromatic tertiary amine derivatives and / or phthalocyanine derivatives, for example, the hole transport layer or the hole injection layer, between the light emitting layer and the anode. Preferably formed.

  As an electron injection material, it has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or light emitting material, and a hole injection layer of excitons generated in the light emitting layer The compound which prevents the movement to and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone and their derivatives However, it is not limited to these. Further, it can be sensitized by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material.

In the organic EL device of the present invention, more effective electron injection materials are metal complex compounds and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, and tris. (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl-8- Quinolinate) (1-naphtholato) aluminum, bis (2-methyl) Le-8-quinolinate) (2-naphtholato) Gallium like, but it is not limited thereto.
As the nitrogen-containing five-membered derivative, for example, oxazole, thiazole, oxadiazole, thiadiazole, and triazole derivatives are preferable. Specifically, 2,5-bis (1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5- Bis (1-phenyl) -1,3,4-oxadiazole, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) 1,3,4-oxadiazole, 2,5 -Bis (1-naphthyl) -1,3,4-oxadiazole, 1,4-bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxa) Diazolyl) -4-tert-butylbenzene], 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-thiadiazole, 2,5-bis (1-naphthyl) ) -1,3,4-thiadiazole, 1,4-bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-triazole, 2,5-bis (1-naphthyl) Examples include, but are not limited to, -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene and the like.

In the organic EL device of the present invention, in the light emitting layer, in addition to at least one aromatic amine derivative selected from the general formula (1), at least one of a light emitting material, a doping material, a hole injecting material, and an electron injecting material. The seed may be contained in the same layer. In order to improve the stability of the organic EL device obtained by the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. Is also possible.
As the conductive material used for the anode of the organic EL device of the present invention, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. Suitable conductive materials for the cathode are those having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like. However, it is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.

  In the organic EL device of the present invention, in order to emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the light emission wavelength region of the device. The substrate is also preferably transparent. The transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film. Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone. , Polysulfone, polyethersulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, Polyvinylidene fluoride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, polypropylene, etc. It is.

For the formation of each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc. and wet film forming methods such as spin coating, dipping, and flow coating is applied. be able to. The film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 μm, but more preferably in the range of 10 nm to 0.2 μm.
In the case of the wet film forming method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, or the like to form a thin film, and any solvent may be used. In any organic thin film layer, an appropriate resin or additive may be used for improving film formability and preventing pinholes in the film. Usable resins include polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, cellulose and other insulating resins and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.

  The organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like. The material of the present invention can be used not only in an organic EL device but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion device, a solar cell, and an image sensor.

Next, the present invention will be described in more detail using examples.
Synthesis Example 1 (Synthesis of Compound (D-1))
Under a stream of argon, 3.8 g (10 mmol) of 6,12-dibromochrysene, 10.1 g (25 mmol) of bis (4- (2-phenylpropan-2-yl) phenyl) amine in a 300 ml three-necked flask with a condenser tube , 0.03 g (1.5 mol%) of palladium acetate, 0.06 g (3 mol%) of tri-t-butylphosphine, 2.4 g (25 mmol) of sodium t-butoxide, and 100 ml of dry toluene were added to 100 ° C. And stirred overnight. After completion of the reaction, the precipitated crystals were collected by filtration and washed with 50 ml of toluene and 100 ml of methanol to obtain 6.5 g of a pale yellow powder. This thing confirmed m / e = 1034 in the measurement of FD-MS (field desorption mass spectrum), and identified it as the compound (D-1).

Synthesis Example 2 (Synthesis of Compound (D-5))
Synthesis was performed in the same manner as in Synthesis Example 1 except that 2,8-dibromochrysene was used instead of 6,12-dibromochrysene. This thing confirmed m / e = 1034 by the measurement of FD-MS, and identified it as the compound (D-5).

Example 1
(1) Manufacture of organic EL elements
A transparent electrode made of indium tin oxide having a thickness of 120 nm was provided on a glass substrate having a thickness of 25 mm × 75 mm × 1.1 mm. This glass substrate was ultrasonically cleaned with isopropyl alcohol, and cleaned by irradiating with ultraviolet rays and ozone.
Next, the glass substrate with a transparent electrode was mounted on a substrate holder in a vapor deposition tank of a vacuum vapor deposition apparatus, and the degree of vacuum in the vacuum tank was reduced to 1 × 10 ⁻³ Pa.
First, N ′, N ″ -bis [4- (diphenylamino) phenyl] -N ′, N ″ -diphenylbiphenyl--covers the transparent electrode on the surface where the transparent electrode is formed. A 4,4′-diamine layer was formed at a deposition rate of 2 nm / sec and a film thickness of 60 nm. This film functions as a hole injection layer.
Next, a layer of N, N, N ′, N′-tetra (4-biphenylyl) benzidine was deposited on the hole injection layer at a deposition rate of 2 nm / sec and a film thickness of 20 nm. This film functions as a hole transport layer.
On the hole transport layer, the compound (2a-1) and the compound (D-1) are deposited at a deposition rate of 2 nm / sec and 0.2 nm / sec, respectively, a film thickness of 40 nm, and a weight ratio of 1-1: 2-1. Co-deposition was performed so that = 40: 2. This film functions as a light emitting layer.
On top of this, tris (8-hydroxyquinolino) aluminum was vapor-deposited at a vapor deposition rate of 2 nm / sec and a film thickness of 20 nm to form an electron transport layer.
Further, an electron injection layer was formed using lithium fluoride at a deposition rate of 0.1 nm / sec and a film thickness of 1 nm.
Finally, a cathode layer was formed with aluminum at a deposition rate of 2 nm / sec and a film thickness of 200 nm.

(2) Evaluation of organic EL element Next, an energization test was performed on this element, and it was confirmed that the emission luminance was 560 cd / m ² at a voltage of 6.5 V and the emission color was blue. Further, when the device was driven at a constant current with an initial light emission luminance of 500 cd / m ² , the half life was 8,000 hours. The obtained results are shown in Table 1.

Examples 2-11
Instead of the compound (2a-1) of Example 1, the compound (2a-2) was carried out in Example 2, (2a-8) was carried out in Example 3, (2a-31) was carried out in Example 4, respectively. In Example 5, (2a-34), in Example 6 (2a′-52), in Example 7 (2a′-55), in Example 8 (2a′-59), in Example 9. An organic EL device was produced in the same manner as in Example 1 except that (2a′-68) was used, (2a′-69) was used in Example 10, and (2b-9) was used in Example 11.
As a result, as shown in Table 1, all blue light emission was observed, the light emission luminance was 530 to 570 cd / m ² , and the half-life was 8,000 hours or more.

Comparative Example 1
An organic EL device was prepared in the same manner as in Example 1 using N, N, N ′, N′-tetra-p-tolylchrysene-6,12-diamine instead of the compound (D-1) in Example 1. did.
Next, an energization test was performed on the device, and it was confirmed that the emission luminance was 560 cd / m ² at a voltage of 6.5 V and the emission color was blue. Further, when the device was driven at a constant current with an initial light emission luminance of 500 cd / m ² , the half life was 4,500 hours.
From the above results, the aromatic amine derivative substituted with a substituent having a benzene ring at the end can prevent the molecular association between the compounds compared to a compound not having the substituent, so that the half-life is increased. I understand.

Example 12
Instead of the compound (2a-1) and the compound (D-1) of Example 1, the same as Example 1 except that the compounds (2a-1) and (D-3) were used in Example 12, respectively. An organic EL element was produced.
When this device was subjected to an energization test, it was confirmed that the emission luminance was 560 cd / m ² at a voltage of 6.5 V and the emission color was blue. Further, when the device was driven at a constant current with an initial light emission luminance of 500 cd / m ² , the half life was 8,000 hours. The obtained results are shown in Table 1.

Examples 13-16
Instead of the compound (2a-1) and the compound (D-1) of Example 1, the compound (2a-1) and (D-5) are used in Example 13, and the compound (2a′-52 is used in Example 14, respectively. ) And (D-5), except that the compounds (2a′-55) and (D-5) were used in Example 15, and the compounds (2a′-59) and (D-5) were used in Example 16. Then, an organic EL device was produced in the same manner as in Example 1.
As a result, as shown in Table 1, all blue light emission was observed, the light emission luminance was 480 to 490 cd / m ² , and the half life was 6,000 hours or more.

Comparative Example 2
In Example 1, instead of the compound (D-1), N, N, N ′, N′-tetrakis (4- (2-phenylpropan-2-yl) phenyl) anthracene-9,10-diamine was used as an organic material. When an EL element was produced, the emission color was increased from blue light emission to green.

  As described above in detail, the organic EL device using the aromatic amine derivative of the present invention emits blue light, has high light emission efficiency, and does not easily deteriorate even when used for a long time, and has a long life. For this reason, it is useful as a light source such as a flat light emitter of a wall-mounted television and a backlight of a display.

Claims (13)

An aromatic amine derivative represented by the following general formula (1).

[Wherein Ar ₀ represents a substituted or unsubstituted chrysenylene group. Ar ₁ and Ar ₃ are each a 4- (2-phenylpropan-2-yl) phenyl group represented by the following general formula (2).

Ar ₂ and Ar ₄ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms. Ar ₂ and Ar ₄ may be the same or different. ] The aromatic amine derivative according to claim 1, wherein -NAr ₁ Ar ₂ is bonded to the 2-position of the substituted or unsubstituted chrysenylene group, and -NAr ₃ Ar ₄ is bonded to the 8-position. The aromatic amine derivative according to claim 1, wherein -NAr ₁ Ar ₂ is bonded to the 6-position of the unsubstituted chrysenylene group and -NAr ₃ Ar ₄ is bonded to the 12-position. The aromatic amine derivative according to claim 1, wherein all of Ar _{1 to} Ar ₄ in the general formula (1) are 4- (2-phenylpropan-2-yl) phenyl groups represented by the general formula (2). .   The aromatic amine derivative according to any one of claims 1 to 4, which is a light-emitting material for an organic electroluminescence device.   The aromatic amine derivative according to any one of claims 1 to 4, which is a blue light emitting material for organic electroluminescence devices.   The aromatic amine derivative according to claim 1, which is a doping material for an organic electroluminescence device.   In the organic electroluminescent element in which the organic thin film layer composed of a single layer or a plurality of layers including at least a light emitting layer is sandwiched between the cathode and the anode, at least one layer of the organic thin film layer is any one of claims 1 to 4. The organic electroluminescent element which contains the aromatic amine derivative of description alone or as a component of a mixture.   The organic electroluminescent device according to claim 8, wherein the aromatic amine derivative is one according to claim 4.   The organic electroluminescent element according to claim 8, wherein the light emitting layer contains the aromatic amine derivative according to claim 1. The said light emitting layer contains the aromatic amine derivative in any one of Claims 1-4 as a doping material, and contains the anthracene derivative represented by the following general formula (i) as a host material. Organic electroluminescence element.

(In the formula, A ₁ and A ₂ are each independently a group derived from a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, and R _{1 to} R ₈ are each independently a hydrogen atom. Substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted carbon A cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group (the aryl moiety has 6 to 50 carbon atoms, the alkyl moiety has 1 to 50 carbon atoms), A substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group (the alkyl moiety is a carbon number) 50), a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a group selected from nitro group and a hydroxyl group). The organic electroluminescent element according to claim 11, wherein in the formula (i), A ₁ and A ₂ are different groups. The said light emitting layer contains the aromatic amine derivative in any one of Claims 1-3 as a doping material, and contains the pyrene derivative represented by the following general formula (ii) as a host material. Organic electroluminescence element.

(In the formula, Ar ₅ and Ar ₆ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms.
L ₁ and L ₂ are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group.
s is an integer of 0 to 2, p is an integer of 1 to 4, q is an integer of 0 to 2, and r is an integer of 0 to 4.
L ₁ or Ar ₅ is bonded to any one of positions 1 to ₅ of pyrene, and L ₂ or Ar ₆ is bonded to any of positions 6 to 10 of pyrene.
However, when p + r is an even number, Ar ₅ , Ar ₆ , L ₁ and L ₂ satisfy the following (1) or (2).
(1) Ar ₅ ≠ Ar ₆ and / or L ₁ ≠ L ₂ (where ≠ indicates a group having a different structure)
(2) When Ar ₅ = Ar ₆ and L ₁ = L ₂
(2-1) s ≠ q and / or p ≠ r, or
(2-2) When s = q and p = r,
(2-2-1) L ₁ and L ₂ or pyrene are bonded to different bonding positions on Ar ₅ and Ar ₆ , respectively. (2-2-2) L ₁ and L ₂ or pyrene is bonded If it is bonded to the same position of Ar ₅ and Ar _6, when the substitution position of pyrene L ₁ and L ₂ or Ar ₅ and Ar ₆ are 1- and 6-position, or 2- and 7-position There is no. )