JP2006265108A - Terphenyl derivative and organic electroluminescent device utilizing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent device having high luminous efficiency and long life and a terphenyl derivative for achieving the device. <P>SOLUTION: The present invention provides the terphenyl derivative having a specific structure, and the organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers containing at least a luminous layer contains at least one kind of material selected from the terphenyl derivative alone or as a component of the mixture, in the organic electroluminescent device in which the organic thin film is held between an anode and a cathode. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a terphenyl derivative and an organic electroluminescence (EL) element using the terphenyl derivative, and more particularly relates to an organic EL element having high emission efficiency and a long lifetime, and a terphenyl derivative that realizes the organic EL element.

  An organic EL element is a self-luminous element utilizing the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. Eastman Kodak's C.I. W. Organic materials have been constructed since Tang et al. Reported on low-voltage driven organic EL devices using stacked devices (CW Tang, SA Vanslyke, Applied Physics Letters, 51, 913, 1987, etc.) Research on organic EL elements as materials has been actively conducted. Tang et al. Use tris (8-hydroxyquinolinol aluminum) for the light emitting layer and a triphenyldiamine derivative for the hole transport layer. The advantages of the stacked structure are that it increases the efficiency of hole injection into the light-emitting layer, blocks the electrons injected from the cathode, increases the generation efficiency of excitons generated by recombination, and generates in the light-emitting layer For example, confining excitons. As in this example, the element structure of the organic EL element includes a hole transport (injection) layer, a two-layer type of an electron transport light-emitting layer, or a hole transport (injection) layer, a light-emitting layer, and an electron transport (injection) layer. A three-layer type is well known. In such a stacked structure element, the element structure and the formation method are devised in order to increase the recombination efficiency of injected holes and electrons.

In addition, chelating complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives and the like are known as light emitting materials. It is reported that light emission in the visible region from red to red is obtained, and realization of a color display element is expected (for example, Patent Document 1, Patent Document 2, Patent Document 3 and the like).
In addition, Patent Documents 4 to 6 disclose devices using symmetrical bisanthracene derivatives as light emitting materials. Although such a symmetric bisanthracene derivative is used as a blue light emitting material, improvement in device lifetime has been demanded.

JP-A-8-239655 JP 7-138561 A JP-A-3-200289 JP-A-8-12600 JP 2000-344691 A Japanese Patent Application Laid-Open No. 2004-2351

  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 high luminous efficiency and a long lifetime and a novel terphenyl derivative that realizes the organic EL device.

  As a result of intensive studies to achieve the above object, the present inventors have used a terphenyl derivative having a specific structure represented by the following general formula (1) as a material for an organic thin film layer in an organic EL device. The present inventors have found that an organic EL device having high luminous efficiency and a long lifetime can be obtained, and the present invention has been completed.

That is, the present invention provides a terphenyl derivative represented by the following general formula (1).

[Wherein, X ₁ represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms.
R _{1 to} R ₃ and A _{1 to} A ₂ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted nucleus atom having 5 to 50 atoms. An aromatic heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, A substituted or unsubstituted aralkyl group having 5 to 50 carbon atoms and 6 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 nuclear carbon atoms A group, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group.
a and b are each an integer of 1 to 5, and when the number is 2 or more, a plurality of A _{1 to} A ₂ may be the same or different. R _{1 to} R ₃ and A _{1 to} A ₂ may be bonded together to form a cyclic structure.
m is an integer of 1 to 4, and when it is 2 or more, the structures in () may be the same or different.
However, A < ₁ > and / or A < ₂ > is a substituted or unsubstituted C1-C6 alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group. ]

  Further, the present invention provides an organic EL device in which an organic thin film layer composed of one or more layers including at least a light emitting layer is sandwiched between an anode and a cathode, wherein the organic thin film layer is at least one selected from the terphenyl derivatives. The organic EL element which contains these as a component of single or a mixture is provided.

  The organic EL device containing the terphenyl derivative of the present invention has high luminous efficiency and a long lifetime.

The terphenyl derivative of the present invention is represented by the following general formula (1).

In the general formula (1), X ₁ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms.
Examples of the aromatic hydrocarbon group for X ₁ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, and a 9- (10-phenyl) anthryl group. 9- (10-naphthyl-1-yl) anthryl group, 9- (10-naphthyl-2-yl) anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9 -Phenanthryl group, 6-chrycenyl 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-turf Enyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, Examples of the 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, and the like and groups having a corresponding valence depending on the value of m in these groups.
Among these, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9- (10-phenyl) anthryl group, a 9- (10-naphthyl-1-yl) anthryl group, and a 9- (10-naphthyl- group) are preferable. 2-yl) anthryl group, 9-phenanthryl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-tolyl group, They are m-tolyl group, p-tolyl group, and pt-butylphenyl group.

Examples of the aromatic heterocyclic group of X ₁ include pyrrole residue, furan residue, thiophene residue, silole residue, indole residue, benzofuran residue, benzothiophene residue, pyrazole residue, isoxazole residue, Isothiazole residue, isobenzofuran residue, isoindole residue, indolizine residue, indazole residue, benzisoxazole residue, benzoisothiazole residue, imidazole residue, oxazole residue, thiazole residue, benzo Imidazole residue, benzoxazole residue, benzothiazole residue, dibenzofuran residue, dibenzothiophene residue, dibenzoisoxazole residue, dibenzoisothiazole residue, dibenzosilolyl residue, pyridine residue, quinoline residue, Isoquinoline residue, pyridazine residue, pyrimidine residue, pyrazine residue Cinnoline residue, naphthyridine residue, phthalazine residue, quinazoline residue, quinoxaline residue, acridine residue, phenanthridine residue, xanthene residue, phenoxazine residue, phenothiazine residue, phenazine residue, perimidine residue Benzoquinoline residue, 1,10-phenanthroline residue, 1,7-phenanthroline residue, 4,7-phenanthroline residue, thianthrenyl residue, pteridine residue, carbazole residue, β- Among carboline residues, purine residues and the like, groups having a corresponding valence can be mentioned depending on the value of m.
Among these, a pyridine residue, a pyrrole residue, a furan residue, a thiophene residue, a silole residue, a pyridine residue, a pyridazine residue, and a birimidine residue are preferable.

Examples of the substituent for X ₁ include an alkyl group (methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl 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-dihydroxy Isopropyl 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-dichloro Ethyl 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-cyano Isobutyl 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, cyclopropyl Group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group, etc.), alkoxy group having 1 to 6 carbon atoms (ethoxy group) , Methoxy group, i-propoxy group, n-propoxy group, s-butoxy group, t-butoxy group, pentoxy group, hexyl Xyl group, cyclopentoxy group, cyclohexyloxy group, etc.), an aryl group having 5 to 40 nuclear atoms, an amino group substituted with an aryl group having 5 to 40 nuclear atoms, and an aryl group having 5 to 40 nuclear atoms. An ester group having an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, a halogen atom, and the like.
Among these, an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms are preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, and a methyl group, an ethyl group, an i-propyl group, and an n-propyl group. N-butyl, s-butyl, t-butyl, n-pentyl, cyclopentyl, n-hexyl and cyclohexyl are particularly preferred.

In the general formula (1), R _{1 to} R ₃ and A _{1 to} A ₂ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted group. Aromatic heterocyclic group having 5 to 50 nuclear atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, substituted or unsubstituted carbon number 1 to 50 alkoxy groups, substituted or unsubstituted aralkyl groups having 5 to 50 carbon atoms and 6 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 50 carbon atoms, substituted or unsubstituted nuclei An arylthio group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; Sil group.

Examples of the substituted or unsubstituted aromatic hydrocarbon group for R _{1 to} R ₃ and A _{1 to} A ₂ include the same examples as the aromatic hydrocarbon group for X ₁ .
Examples of the substituted or unsubstituted aromatic heterocyclic group for R _{1 to} R ₃ and A _{1 to} A ₂ include the same examples as the aromatic heterocyclic group for X ₁ .
Examples of substituted or unsubstituted alkyl groups of R _{1 to} R ₃ and A _{1 to} A ₂ include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl 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, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloro Propyl 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-sia Ethyl 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-tri Examples thereof include a nitropropyl group.
Among these, preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, and n-pentyl group, and particularly preferred are isopropyl group, s -A butyl group and a t-butyl group.

Examples of the substituted or unsubstituted cycloalkyl group represented by R _{1 to} R ₃ and A _{1 to} A ₂ include, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a 1-adamantyl group. , 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.
A substituted or unsubstituted alkoxy group R ₁ to R ₃ and A ₁ to A ₂ is a group represented by -OY, examples of Y are examples similar to the alkyl group.

Examples of substituted or unsubstituted aralkyl groups of R _{1 to} R ₃ and A _{1 to} A ₂ 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-butyl Mobenzyl 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 of R _{1 to} R ₃ and A _{1 to} A ₂ is represented as —OY ′, and examples of Y ′ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, 1- Anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 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-tri Group, m-tolyl group, p-tolyl group, pt-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, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group 3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-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-benzofuran group Group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-iso Benzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-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, 1-phenanthryl Nyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl 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-phenanthroline- 2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanth Lorin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8- Phenanthrolin-2-yl group, 1, 8-phenanthroline-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl Group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6 -Yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group, 1,10-phenanthroline 2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phena Throlin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9- Phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group, 2, 9-phenanthroline-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl Group, 2,8-phenanthroline-9-yl group, 2,8-phenanthroline-10 Yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin- 5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group, 2,7-phenance Lorin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazani Group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5- Yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrole- 4-yl group, 3- (2-phenylpropyl) pyrrol-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, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group, 4-t-butyl 3-indolyl group and the like can be mentioned.

The substituted or unsubstituted arylthio group of R _{1 to} R ₃ and A _{1 to} A ₂ is represented by —SY ′, and examples of Y ′ include the same examples as Y ′ of the aryloxy group.
The substituted or unsubstituted alkoxycarbonyl group of R _{1 to} R ₃ and A _{1 to} A ₂ is represented as —COOZ, and examples of Z include the same examples as the alkyl group.
Examples of the substituted or unsubstituted silyl group of R _{1 to} R ₃ and A _{1 to} A ₂ include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, and a propyldimethylsilyl group. It is done.
Examples of the halogen atom for R _{1 to} R ₃ and A _{1 to} A ₂ include fluorine, chlorine, bromine, iodine and the like.
Examples of the substituent for R _{1 to} R ₃ and A _{1 to} A ₂ include the same examples as the substituent for X ₁ .

In the general formula (1), a and b are each an integer of 1 to 5, preferably 1 to 3, and when 2 or more, a plurality of A _{1 to} A ₂ may be the same or different. R _{1 to} R ₃ and A _{1 to} A ₂ may be bonded together to form a cyclic structure.
Examples of the cyclic structure include cycloalkanes having 4 to 12 carbon atoms such as cyclobutane, cyclopentane, cyclohexane, adamantane and norbornane, cycloalkenes having 4 to 12 carbon atoms such as cyclobutene, cyclopentene, cyclohexene, cycloheptene and cyclooctene, C6-C12 cycloalkadiene such as cyclohexadiene, cycloheptadiene, cyclooctadiene, aromatic ring having 6-50 carbon atoms such as benzene, naphthalene, phenanthrene, anthracene, pyrene, chrysene, acenaphthylene, imidazole, pyrrole , Furan, thiophene, pyridine, etc.

In General formula (1), m is an integer of 1-4, 1-3 are preferable, and when it is two or more, the structure in several () may be the same or different.
However, in General formula (1), A < ₁ > and / or A < ₂ > is a substituted or unsubstituted C1-C6 alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group.
In the general formula (1), A _{1 to} A ₂ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms. Preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, cyclohexyl group, norbornel group, and adamantyl group. , Isopropyl group, s-butyl group, and t-butyl group are particularly preferable.

The terphenyl derivative represented by the general formula (1) of the present invention is preferably represented by the following general formula (2) or (3).

In the general formula (2), X ₂ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms. Specific examples, preferred examples, and substituents are the same as those of X _{1 in the} general formula (1).
In the general formula (2), R _{1 to} R ₃ and A _{1 to} A ₂ are the same as described above.
In the general formula (2), a to c are each an integer of 1 to 5, preferably 1 to 3, and when 2 or more, a plurality of A _{1 to} A ₂ and X ₂ are the same or different. May be. Further, X _2, R ₁ ~R ₃ and A ₁ to A _2, which may be bonded to form a cyclic structure with adjacent ones, as the examples of the may be mentioned as examples of the cyclic structure.
In the general formula (2), m is the same as described above, and when the number is 2 or more, the structures in () may be the same or different.
However, in General formula (2), A < ₁ > and / or A < ₂ > are a substituted or unsubstituted C1-C6 alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group.
In the general formula (2), A _{1 to} A ₂ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms. Preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, cyclohexyl group, norbornel group, and adamantyl group. , Isopropyl group, s-butyl group, and t-butyl group are particularly preferable.

In the general formula (3), X ₃ represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted divalent aromatic complex having 5 to 50 nuclear atoms. Specific examples and preferred examples of the cyclic group include bivalent examples among the same examples as X _{1 in the} general formula (1), and the same examples can be given to substituents.
In the general formula (3), R _{1 to} R ₆ and A _{1 to} A ₄ are the same as R _{1 to} R ₃ and A _{1 to} A ₂ , respectively.
In the general formula (3), to b and d~e is an integer from 1 to 5, respectively, different preferable to be 1 to 3, when 2 or more, even more A ₁ to A ₄ are each the same It may be. R _{1 to} R ₆ and A _{1 to} A ₄ may be bonded together to form a cyclic structure, and examples of the cyclic structure include the same examples as described above.
However, in General formula (3), A < ₁ > and / or A < ₂ > is a substituted or unsubstituted C1-C6 alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group, A ₃ and / or A ₄ is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms.

In the general formula (3), each of A _{1 to} A ₄ is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms. And A _{1 to} A ₄ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms, and It is more preferable that A _{1 to} A ₄ are all the same group, and it is particularly preferable that the A _{1 to} A ₄ are each independently a substituted or unsubstituted branched alkyl group having 3 to 6 carbon atoms.
Examples of the alkyl group having 1 to 6 carbon atoms and the cycloalkyl group having 3 to 10 nuclear carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t- A butyl group, an n-pentyl group, a cyclohexyl group, a norbornel group, and an adamantyl group are preferable, and an isopropyl group, a s-butyl group, and a t-butyl group are particularly preferable.

Specific examples of the terphenyl derivative represented by the general formulas (1) to (3) in the present invention are shown below, but are not limited to these exemplified compounds.

Next, the manufacturing method of the terphenyl derivative of this invention is demonstrated.
The production method of the terphenyl derivative represented by the general formula (1) of the present invention is not particularly limited, and may be produced by a known method, for example, J. Org. Chem., 51.3165 (1986) (H. Hart Et al., J. Org. Chem., 57.2721 (1982) (H. Hart et al.), Synthesls 1455 (1996) (H. Hart et al.), J. Organomet. Chem., 643 461 (2002) (PPPower et al.) The terphenyl derivative obtained by the described method is derived into boronic acid, and the terphenyl derivative of the present invention is produced by a coupling reaction between the obtained boronic acid and an aryl halide.

The terphenyl derivative of the present invention is preferably a light emitting material for an organic EL device, and is preferably used even if it is a host material or a doping material for an organic EL device.
The organic EL device of the present invention is an organic electroluminescence device in which an organic thin film layer comprising at least one light emitting layer or a plurality of layers is sandwiched between an anode and a cathode, wherein the organic thin film layer is formed from the terphenyl derivative of the present invention. Contains at least one selected as a component of the mixture alone or as a mixture.
In the present invention, the light emitting layer preferably contains the terphenyl derivative of the present invention alone or as a component of a mixture, and the light emitting layer contains 0.1 to 100% by weight of the terphenyl derivative as a host material. Then, it is preferable to contain 20 to 100% by weight, more preferably 0.1 to 20% by weight as a doping material.

As the multi-layer organic EL element, (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) A layer / cathode) and the like are included.
In addition to the terphenyl 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. By making the organic EL element have a multi-layer structure, it is possible to prevent a decrease in luminance and life due to quenching. 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 that can be used in the light emitting layer together with the terphenyl derivative of the present invention include naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclo Condensed condensed aromatic compounds such as pentadiene, fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthracenyl) benzene, and the like Derivatives, tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4- (phenylphenolinato) aluminum and other organometallic complexes, triarylamine 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 derivatives, etc. However, it is not limited to these.

  The hole injection material 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 the 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, acylhydrazone, 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) derivative include H ₂ Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl ₂ SiPc, (HO) AlPc, (HO) GaPc, Although there exist phthalocyanine derivatives and naphthalocyanine derivatives, such as VOPc, TiOPc, 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 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 any one of the organic thin film layers, in addition to the terphenyl derivative, at least one of a light emitting material, a doping material, a hole injection material, and an electron injection material is formed in the same layer. It may be contained. 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.

EXAMPLES Next, although an Example demonstrates this invention further in detail, this invention is not limited at all by these examples.
Synthesis Example 1 (Synthesis of Compound (17))
(1) Synthesis of boronic acid Under a nitrogen stream, 1.47 g (10 mmo1) of 1,3-dichlorobenzene and 20 ml of dry THF (tetrahydrofuran) were added to a 200 ml three-necked flask and cooled to -78 ° C. Subsequently, 10 ml (16 mmol) of n-butyllithium was slowly added, followed by stirring for 2 hours. Separately prepared 30 ml of 4-t-butylphenylmagnesium bromide (30 mmo1, THF solution) was added and stirred at -78 ° C for 1 hour, followed by heating and stirring for 1 hour. Thereafter, the mixture was cooled to -78 ° C., 5.6 g (30 mmo1) of 2-isobropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added, and the mixture was stirred for 3 hours, and further at room temperature. Bonded for 1 hour. After completion of the reaction, dilute hydrochloric acid was added to the reaction solution at 0 ° C., and the organic layer was separated with diethyl ether and washed with water and saturated brine. After drying with magnesium sulfate, the rotary evaporator was evaporated. Purification by column chromatography (silica gel, developing solvent chloroform: hexane = 1: 2) gave the target boronic acid 3 g (white solid, yield 64%). The melting point was 112-117 ° C.
(2) Synthesis of Compound (17) A Pd catalyst was prepared by the following method. 56 mg (O.25 mmo1) of palladium acetate was placed in the test bowl and stoppered with a rubber septum. 10 ml of xylene bubbled with nitrogen was put therein, and after ultrasonication, nitrogen bubbling was performed. Thereto was added O.3 ml of hetri-t-butylphosphine (d = O.7), and the mixture was allowed to stand overnight by sonication to prepare a Pd catalyst (O.025M).
Under a nitrogen stream, in a 50 ml three-necked flask, 1.9 g (4 mmo1) boronic acid, 9,10-bis (p-bromophenyl) anthracene) O.88 g (1.8 mmo1), Pd catalyst O.02 mmo1, 1.7 g (12 mmol) calcium carbonate ), 8 ml of toluene and 6 ml of water were added, and the mixture was refluxed for 12 hours. After neutralization, the reaction solution was concentrated, extracted with benzene, and washed with saturated brine. After drying with magnesium sulfate, the solvent was distilled off with a rotary evaporator. Purification by column chromatography (silica gel, developing solvent chloroform: hexane = 1: 2) afforded 0.5 g (white solid, 28% yield) of the desired compound (17). This was identified as Compound (17) by measurement of ¹ H-NMR spectrum (FIG. 1), IR spectrum (FIG. 2) and FAB-MS (Fast atom bombardment mass spoctrometry) (yield 28%).

Example 1
A transparent electrode made of indium tin oxide having a thickness of 120 nm was provided on a glass substrate having a size of 25 × 75 × 1.1 mm. After cleaning this glass substrate by irradiating it with ultraviolet rays and ozone, this substrate was placed in a vacuum deposition apparatus.
First, N ′, N ″ -bis [4- (diphenylamino) phenyl] -N ′, N ″ -diphenylbiphenyl-4,4′-diamine was deposited to a thickness of 60 nm as a hole injection layer. After that, N, N, N ′, N′-tetrakis (4-biphenyl) -4,4′-benzidine was vapor-deposited to a thickness of 20 nm as a hole transport layer thereon. Next, the compound (17) and N- (4- (4- (4- (di-p-tolylamino) styryl) styryl) phenyl) -4-methyl-Np-tolylbenzenamine were mixed at a weight ratio of 40: 2 was co-evaporated to form a light emitting layer having a thickness of 40 nm.
Next, tris (8-hydroxyquinolinato) aluminum was deposited to a thickness of 20 nm as an electron injection layer. Next, lithium fluoride was deposited to a thickness of 1 nm, and then aluminum was deposited to a thickness of 150 nm. This aluminum / lithium fluoride functions as the cathode. In this way, an organic EL element was produced.
When a current test was performed on the obtained device, blue light emission with a light emission efficiency of 9.5 cd / A and a light emission luminance of 950 cd / m ² was obtained at a current density of 10 mA / cm ² . When a direct current continuous test was performed at an initial luminance of 500 cd / m ² , the luminance half life was 20000 hours or more.

Example 2
An organic EL device was produced in the same manner as in Example 1 except that the compound (16) was used instead of the compound (17).
When a current test was performed on the obtained device, blue light emission with a light emission efficiency of 9.0 cd / A and a light emission luminance of 900 cd / m ² was obtained at a current density of 10 mA / cm ² . When a direct current continuous test was performed at an initial luminance of 500 cd / m ² , the luminance half life was 20000 hours or more.

Comparative Example 1
An organic EL device was produced in the same manner as in Example 1, except that 4,4′-bis (2,2-diphenylvinyl) biphenyl was used instead of the compound (17).
When a current test was performed on the obtained device, blue light emission with a light emission efficiency of 7.5 cd / A and a light emission luminance of 750 cd / m ² was obtained at a current density of 10 mA / cm ² . When a DC continuous energization test was performed at an initial luminance of 500 cd / m ² , the luminance half life was 5000 hours.

  As described above in detail, the organic EL device using the terphenyl derivative of the present invention has high luminous efficiency and a long lifetime. For this reason, it is extremely useful as a highly practical organic EL device.

¹ is a diagram showing a ¹ NMR spectrum of a terphenyl derivative of the present invention obtained in Synthesis Example 1. FIG. 1 is a diagram showing an IR spectrum of a terphenyl derivative of the present invention obtained in Synthesis Example 1. FIG.

Claims (10)

A terphenyl derivative represented by the following general formula (1).

[Wherein, X ₁ represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms.
R _{1 to} R ₃ and A _{1 to} A ₂ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted nucleus atom having 5 to 50 atoms. An aromatic heterocyclic group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, A substituted or unsubstituted aralkyl group having 5 to 50 carbon atoms and 6 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 nuclear carbon atoms A group, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group.
a and b are each an integer of 1 to 5, and when the number is 2 or more, a plurality of A _{1 to} A ₂ may be the same or different. R _{1 to} R ₃ and A _{1 to} A ₂ may be bonded together to form a cyclic structure.
m is an integer of 1 to 4, and when it is 2 or more, the structures in () may be the same or different.
However, A < ₁ > and / or A < ₂ > is a substituted or unsubstituted C1-C6 alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group. ] The terphenyl derivative according to claim 1, which is represented by the following general formula (2).

[Wherein, X ₂ represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms.
R _{1 to} R ₃ and A _{1 to} A ₂ are the same as described above.
Each of a to c is an integer of 1 to 5, and when it is 2 or more, the plurality of A _{1 to} A ₂ and X ₂ may be the same or different. X ₂ , R _{1 to} R ₃ and A _{1 to} A ₂ may be bonded together to form a cyclic structure.
m is the same as above, and when it is 2 or more, the structures in () may be the same or different.
However, A < ₁ > and / or A < ₂ > is a substituted or unsubstituted C1-C6 alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group. ] The A _{1 to} A ₂ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms. A terphenyl derivative of The terphenyl derivative according to claim 1, which is represented by the following general formula (3).

[Wherein, X ₃ represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 50 nuclear atoms. is there.
R _{1 to} R ₆ and A _{1 to} A ₄ are the same as R _{1 to} R ₃ and A _{1 to} A ₂ , respectively.
ab and de are each an integer of 1 to 5, and when the number is 2 or more, the plurality of A _{1 to} A ₄ may be the same or different. R _{1 to} R ₆ and A _{1 to} A ₄ may be bonded together to form a cyclic structure.
However, A ₁ and / or A ₂ is an alkyl group or a substituted or unsubstituted cycloalkyl group having ring carbon atoms of 3 to 10 substituted or unsubstituted 1 to 6 carbon atoms, and A ₃ and / or A ₄ is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms. ] 5. The tellurium according to claim ₄ , wherein each of A _{1 to} A ₄ is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms. Phenyl derivatives. A _{1 to} A ₄ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 10 nuclear carbon atoms, and A _{1 to} A _4. The terphenyl derivatives according to claim 4, wherein all are the same groups. The terphenyl derivative according to claim 4, wherein each of A _{1 to} A ₄ is independently a substituted or unsubstituted branched alkyl group having 3 to 6 carbon atoms.   It is a luminescent material for organic electroluminescent elements, The terphenyl derivative in any one of Claims 1-7.   In the organic electroluminescent element in which the organic thin film layer which consists of the organic thin film layer which consists of a single layer or multiple layers including at least a light emitting layer between a cathode and an anode, at least one layer of this organic thin film layer is in any one of Claims 1-7. An organic electroluminescence device containing a terphenyl derivative alone or as a component of a mixture. The organic electroluminescent element according to claim 9, wherein the light emitting layer contains the terphenyl derivative alone or as a component of a mixture.

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