# US 8,785,006 B2 · Organic electroluminescence device and anthracene derivative

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,785,006 B2
- Document ID: US8785006B2
- Status: Granted
- Kind: B2
- Application number: 13/482,031
- Filed: 2012-05-29
- Published: 2012-09-20
- Granted: 2014-07-22
- Earliest claimed: 2010-10-12
- Assignees: Idemitsu Kosan Co., Ltd.
- Applicants: Hidetsugu Ikeda; Motohisa Ido; Masakazu Funahashi
- Inventors: Hidetsugu Ikeda; Motohisa Ido; Masakazu Funahashi
- Web page: https://patentgrep.com/patent/US8785006B2

## CPC

- C07C 13/66: the condensed ring system contains only four rings
- C07C 15/28: Anthracenes
- C07C 43/20: having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C 43/257: having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C09K 11/06: containing organic luminescent materials
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07C 2603/24: Anthracenes; Hydrogenated anthracenes
- C07C 2603/26: Phenanthrenes; Hydrogenated phenanthrenes
- C07C 2603/40: containing four condensed rings
- C07C 2603/50: Pyrenes; Hydrogenated pyrenes
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y10S 428/917: Electroluminescent
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

An anthracene derivative having a specific asymmetric structure is provided. The asymmetric anthracenes are useful in an organic electroluminescence device and exhibit efficient light emission and a long performance lifetime.

## Claims

### Claim 1

A light emitting material for an organic electroluminescence device, comprising an anthracene derivative of formula (2):
wherein
Ar is selected from the group consisting of 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, and a fluoranthenyl group, each being optionally substituted;
Ar′ is selected from the group consisting of a phenyl group, 1-anthryl group, 2-anthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, 1-naphthyl group, 2-naphthyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 9-phenanthryl group 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group and fluoranthenyl group, each being optionally substituted;
X is a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxyl group having 5 to 50 nuclear atoms, a substituted or unsubstituted arylthio group having 5 to 50 nuclear atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, carboxyl group, a halogen atom, cyano group, nitro group or hydroxyl group;
a and b are each an integer of 0 to 4; and
n is an integer of 1 to 3 and, when n represents 2 or 3, two or three groups represented by:
may each be the same or different, and
wherein the light emitting material is located in the light emitting layer of an organic electroluminescence device.

### Claim 2 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein Ar is selected from the group consisting of:
wherein Ar1 is a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms.

### Claim 3 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein a and b are both zero.

### Claim 4 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein X is an aromatic group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

### Claim 5 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein n is 1.

### Claim 6 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein a and b are both zero and n is 1.

### Claim 7 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein X is an unsubstituted group selected from the group consisting of a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyradinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolyl group, a 7-indolyl group, a 1 isoindolyl group, a 2-isoindolyl group, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group, a 6-a isoindolyl group, a 7-isoindolyl group, a 2-furyl group, 3-furyl group, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranyl group, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a 7-isobenzofuranyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a 6-phenanthridinyl group, a 7-phenanthridinyl group, a 8-phenanthridinyl group, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a 1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a 4-acridinyl group, a 9-acridinyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, and a t-butyl group.

### Claim 8 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein the optional substituent of Ar, Ar′ and X is selected from the group consisting of a halogen atom, a hydroxyl group, a nitro group, a cyano group, an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted cycloalkyl group, an unsubstituted alkoxyl group, an unsubstituted aromatic heterocyclic group, an unsubstituted aralkyl group, an unsubstituted aryloxyl group, an unsubstituted arylthio group, an unsubstituted alkoxycarbonyl group and a carboxyl group.

### Claim 9 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein
Ar is an unsubstituted group selected from the group consisting of a 1-naphthyl group, a 2-naphthyl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, and a 4-phenanthryl group;
Ar′ is an unsubstituted group selected from the group consisting of a phenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-naphtyl group, a 2-naphtyl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, and a 4-phenanthryl group;
X is an unsubstituted group selected from the group consisting of a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a methyl group, and a t-butyl group;
a is 0 or 1;
b is 0 or 1; and
n is 1.

### Claim 10 (depends on 1)

The light emitting material for an organic electroluminescence device according to claim 1 wherein
Ar is an unsubstituted 1-naphthyl group or an unsubstituted 2-naphthyl group;
Ar′ is an unsubstituted 1-naphthyl group or an unsubstituted 2-naphthyl group;
a is 0;
b is 0; and
n is 1.