Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-9786846-B2
Application number	US-201514935853-A
Country	US
Kind code	B2
Filing date	Nov 9, 2015
Priority date	Dec 19, 2003
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

Disclosed is a light-emitting material for organic electroluminescent (EL) devices which is composed of an asymmetric anthracene derivative of a specific structure. Also disclosed are a material for organic EL devices and an organic EL device wherein an organic thin film layer composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode. At least one layer composed of the organic thin film layer contains the material for organic EL devices by itself or as a component of a mixture. Consequently, the organic EL device has a high efficiency and a long life. Also disclosed are a light-emitting material for organic EL devices and material for organic devices which enable to realize such an organic EL device.

First claim

What we claim is:

1. A light emitting material for an organic electroluminescent device comprising an asymmetric anthracene derivative represented by formula (1):

wherein
A 1 represents 2-naphthyl group;
A 2 represents 2-naphthyl group, 1-pyrenyl group, 2-pyrenyl group, or 4-pyrenyl group;
Ar 1 and Ar 2 each independently represent a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50;
R 1 to R 8 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted aromatic hetero ring group having ring atoms of 5 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group;
R 9 to R 10 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and none of R 9 and R 10 is alkenyl group;
Ar 1 , Ar 2 , R 9 and R 10 each may be a plural number, and two neighboring groups thereof may form a saturated or unsaturated ring structure;
the substituent groups at 9th and 10th positions of the anthracene at the core in formula (1) are different from each other; and
a substituent for Ar 1 , Ar 2 , and R 9 and R 10 is a halogen atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group, an aryl group, a cycloalkyl group, an alkoxy group, an aralkyl group, an aryloxy group, an arylthio group, an alkoxycarbonyl group, and a carboxyl group.

2. The light emitting material for the organic electroluminescent device according to claim 1 , wherein Ar 1 and Ar 2 each independently represent any one of a hydrogen atom, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 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-tolyl 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, and 4″-t-butyl-p-terphenyl-4-yl group.

3. The light emitting material for the organic electroluminescent device according to claim 1 , wherein Ar 1 and Ar 2 each independently represent any one of a hydrogen atom 1-naphthyl group, 2-naphthyl group, and 9-phenanthryl group.

4. The light emitting material for the organic electroluminescent device according to claim 1 , wherein the asymmetric anthracene derivative comprises a naphtalene-1-yl group having a substituent at 4th position thereof and/or a substituted or unsubstituted condensed aromatic hydrocarbon ring group having ring carbon atoms of 12 to 20.

5. An organic electroluminescent device comprising at least one organic thin film layer which comprises a light emitting layer and which is interposed between a pair of electrode consisting of an anode and a cathode, wherein the light emitting layer comprises the light emitting material for the organic electroluminescent device according to claim 1 singly or as a component of a mixture thereof.

6. The organic electroluminescent device according to claim 5 , wherein the light emitting layer comprises additionally an arylamine compound.

7. The organic electroluminescent device according to claim 5 , wherein the light emitting layer comprises additionally a styrylamine compound.

8. A material for an organic electroluminescence device comprising an asymmetric anthracene derivative represented by formula (1′):

wherein, A 1 ′ and A 2 ′ each independently represent a substituted or unsubstituted condensed aromatic hydrocarbon ring group having ring carbon atoms of 10 to 20, and at least one of the groups A 1 ′ and A 2 ′ represents a naphtalene-1-yl group having a substituent at 4th position thereof or a substituted or unsubstituted condensed aromatic hydrocarbon ring group having ring carbon atoms of 12 to 20;
Ar 1 and Ar 2 each independently represent a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring having ring carbon atoms of 6 to 50;
R 1 to R 8 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted aromatic hetero ring group having ring atoms of 5 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group;
R 9 to R 10 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and none of R 9 and

Assignees

• Idemitsu Kosan Co

Inventors

• Kubota Mineyuki
• Funahashi Masakazu
• Hosokawa Chishio

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C07C2603/50

  Pyrenes; Hydrogenated pyrenes · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07C15/38

  containing four rings · CPC title

• C07C2603/24

  Anthracenes; Hydrogenated anthracenes · CPC title