# US 8,771,845 B2 · Emissive aryl-heteroaryl compounds

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- Number: US 8,771,845 B2
- Document ID: US8771845B2
- Status: Granted
- Kind: B2
- Application number: 13/925,625
- Filed: 2013-06-24
- Published: 2013-10-31
- Granted: 2014-07-08
- Earliest claimed: 2009-06-29
- Assignees: Nitto Denko Corporation
- Applicants: Nitto Denko Corporation
- Inventors: Shijun Zheng; Jensen Cayas; Sheng Li; Amane Mochizuki; Hyun Sik Chae; Brett T. Harding
- Web page: https://patentgrep.com/patent/US8771845B2

## CPC

- H01L 51/006
- C09K 2211/1033: with oxygen
- C07D 235/18: with aryl radicals directly attached in position 2
- H01L 51/0071
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- H05B 37/00
- C09K 2211/1037: with sulfur
- C07D 277/66: with aromatic rings or ring systems directly attached in position 2
- C09K 2211/1007: Non-condensed systems
- C07D 413/10: linked by a carbon chain containing aromatic rings
- C09K 11/06: containing organic luminescent materials
- H01L 51/0072
- C09K 2211/1011: Condensed systems
- G01J 1/42: using electric radiation detectors (optical or mechanical part G01J1/04; by comparison with a reference light or electric value G01J1/10)
- 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}
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C07D 263/57: Aryl or substituted aryl radicals
- Y10S 428/917: Electroluminescent
- H01L
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- G01J: MEASUREMENT OF INTENSITY, VELOCITY, SPECTRAL CONTENT, POLARISATION, PHASE OR PULSE CHARACTERISTICS OF INFRARED, VISIBLE OR ULTRAVIOLET LIGHT; COLORIMETRY; RADIATION PYROMETRY (light sources F21, H01J, H01K, H05B; investigating properties of materials by optical means G01N)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Disclosed herein are compounds represented by Formula 1, wherein R1, Ar1, X, Ar2, Ar3, and Het are described herein. Compositions and light-emitting devices related thereto are also disclosed.

## Claims

### Claim 1

A compound represented by a formula:
wherein R1 is a C1-10O1-4 ether attaching at an oxygen atom or —R7—NR8R9;
wherein R7 is a single bond or optionally substituted C6-10 aryloxy; and
R8 and R9 are independently optionally substituted C6-10 aryl, wherein R8 and R9 optionally link together form a third ring comprising N;
Ar1 is aryl having 0, 1, 2, 3, or 4 substituents independently selected from C1-3 alkyl and F;
Ar2 is p-interphenylene having 0, 1, 2, 3, or 4 substituents independently selected from C1-3 alkyl and F;
X is O;
Ar3 is p-interphenylene having 0, 1, 2, 3, or 4 substituents independently selected from C1-3 alkyl and F; or Ar3 is a single bond;
Z is NR6, wherein R6 is optionally substituted phenyl, optionally substituted —CH2-phenyl, or optionally substituted (4-halophenyl)methyl; and
R2, R3, R4, and R5 are independently H, optionally substituted C6-30 aryl, C1-10 alkyl, or C1-10 alkoxy.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 is optionally substituted carbazolyl, optionally substituted carbazolylphenoxy, optionally substituted diphenyl amine, optionally substituted diphenylaminophenoxy, or C1-10 alkoxy.

### Claim 3 (depends on 2)

The compound of claim 2 wherein R1 is methoxy,

### Claim 4 (depends on 1)

The compound of claim 1, wherein Ar1 is optionally substituted p-interphenylene.

### Claim 5 (depends on 1)

The compound of claim 1, wherein at least one of Ar1, Ar2, and Ar3 is unsubstituted p-interphenylene.

### Claim 6 (depends on 1)

The compound of claim 1, wherein Z is NR6 and R6 is optionally substituted phenyl.

### Claim 7 (depends on 6)

The compound of claim 6, wherein R1 is selected from the group consisting of optionally substituted diphenyl amine, optionally substituted carbazolyl, optionally substituted p-carbazolylphenoxy, and optionally substituted p-diphenylaminophenoxy.

### Claim 8 (depends on 1)

The compound of claim 1, wherein Ar3 is a single bond.

### Claim 9 (depends on 8)

The compound of claim 8, wherein R1 is optionally substituted diphenyl amine.

### Claim 10 (depends on 8)

The compound of claim 8, wherein R1 is optionally substituted carbazolyl.

### Claim 11 (depends on 1)

The compound of claim 1, wherein Ar3 is p-interphenylene having 0, 1, 2, 3 or 4 substituents independently selected from C1-3 alkyl and F.

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound is selected from:

### Claim 13

A compound represented by a formula:
R1—Ar1—X—Ar2—Ar3-Het
wherein R1 is C1-10 alkoxy, substituted carbazolyl, substituted diphenylamino, optionally substituted carbazolylphenoxy, or optionally substituted diphenylaminophenoxy;
Ar1 is optionally substituted aryl;
Ar2 is p-interphenylene having 0, 1, 2, 3, or 4 substituents independently selected from C1-3 alkyl and F;
X is O;
Ar3 is p-interphenylene having 0, 1, 2, 3, or 4 substituents independently selected from C1-3 alkyl and F; or Ar3 is a single bond; and
Het is optionally substituted benzoimidazolyl.

### Claim 14

A compound represented by a formula:
wherein R1 is C1-10 alkoxy, optionally substituted carbazolylphenoxy, or optionally substituted diphenylaminophenoxy; and
Het is optionally substituted benzoimidazolyl.

### Claim 15 (depends on 14)

The compound of claim 14, wherein the compound is selected from:

### Claim 16 (depends on 1)

A light-emitting device, comprising:
a light-emitting layer comprising a compound according to claim 1.

### Claim 17 (depends on 1)

A method of converting an electric potential difference to light comprising exposing a composition comprising a compound according to claim 1 to an electric potential difference to thereby produce light.

### Claim 18 (depends on 1)

A method of converting light to an electric potential difference comprising exposing a composition comprising a compound according to claim 1 to light to thereby produce an electric potential difference.