# US 9,040,719 B2 · Carbazole derivative, light-emitting element material, light-emitting element, light-emitting device, electronic device, and lighting device

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- Number: US 9,040,719 B2
- Document ID: US9040719B2
- Status: Granted
- Kind: B2
- Application number: 13/961,120
- Filed: 2013-08-07
- Published: 2013-12-05
- Granted: 2015-05-26
- Earliest claimed: 2009-03-31
- Assignees: Semiconductor Energy Laboratory Co., Ltd.
- Applicants: Semiconductor Energy Laboratory Co., Ltd.
- Inventors: Hiroko Nomura; Harue Osaka; Takahiro Ushikubo; Satoshi Seo
- Web page: https://patentgrep.com/patent/US9040719B2

## CPC

- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- 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}
- H05B 33/20: characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- Y10S 428/917: Electroluminescent
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A carbazole derivative represented by the general formula (1) is provided. In the formula, Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; α and β independently represent a substituted or unsubstituted arylene group having 6 to 12 carbon atoms which form a ring; R1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; and R11 to R17 and R21 to R28 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring.

## Claims

### Claim 1

A light-emitting element comprising:
a first electrode;
a layer over the first electrode;
a light-emitting layer over the layer; and
a second electrode over the light-emitting layer,
wherein the layer comprises a carbazole derivative represented by a general formula (1),
wherein Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; α and β independently represent a substituted or unsubstituted arylene group having 6 to 12 carbon atoms which form a ring; R1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; and R11 to R17 and R21 to R28 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring.

### Claim 2 (depends on 1)

A light-emitting device comprising:
the light-emitting element according to claim 1; and
means for controlling the light-emitting element.

### Claim 3 (depends on 2)

An electronic device wherein the light-emitting device according to claim 2 is provided in a display portion.

### Claim 4 (depends on 2)

A lighting device comprising the light-emitting device according to claim 2.

### Claim 5

A light-emitting element comprising:
a first electrode;
a hole-transporting layer over the first electrode;
a light-emitting layer over the hole-transporting layer; and
a second electrode over the light-emitting layer,
wherein the hole-transporting layer comprises a carbazole derivative represented by a general formula (1),
wherein Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; α and β independently represent a substituted or unsubstituted arylene group having 6 to 12 carbon atoms which form a ring; R1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; and R11 to R17 and R21 to R28 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring.

### Claim 6 (depends on 5)

A light-emitting device comprising:
the light-emitting element according to claim 5; and
means for controlling the light-emitting element.

### Claim 7 (depends on 6)

An electronic device wherein the light-emitting device according to claim 6 is provided in a display portion.

### Claim 8 (depends on 6)

A lighting device comprising the light-emitting device according to claim 6.

### Claim 9

A light-emitting element comprising:
a first electrode;
a hole-injecting layer over the first electrode;
a light-emitting layer over the hole-injecting layer; and
a second electrode over the light-emitting layer,
wherein the hole-injecting layer comprises a carbazole derivative represented by a general formula (1),
wherein Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; α and β independently represent a substituted or unsubstituted arylene group having 6 to 12 carbon atoms which form a ring; R1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; and R11 to R17 and R21 to R28 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring.

### Claim 10 (depends on 9)

A light-emitting device comprising:
the light-emitting element according to claim 9; and
means for controlling the light-emitting element.

### Claim 11 (depends on 10)

An electronic device wherein the light-emitting device according to claim 10 is provided in a display portion.

### Claim 12 (depends on 10)

A lighting device comprising the light-emitting device according to claim 10.

### Claim 13 (depends on 1)

The light-emitting device according to claim 1, wherein the light-emitting layer is in contact with the layer.
