# US 9,040,175 B2 · Electronic device comprising an organic semiconducting material

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- Number: US 9,040,175 B2
- Document ID: US9040175B2
- Status: Granted
- Kind: B2
- Application number: 13/699,532
- Filed: 2011-06-08
- Published: 2013-08-08
- Granted: 2015-05-26
- Earliest claimed: 2010-06-10
- Assignees: Novaled GmbH
- Applicants: Omrane Fadhel; Ramona Pretsch
- Inventors: Omrane Fadhel; Ramona Pretsch
- Web page: https://patentgrep.com/patent/US9040175B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 50/121: {for assisting energy transfer, e.g. sensitization}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/656: {comprising two or more different heteroatoms per ring (H10K85/652 takes precedence)}
- H10K 50/14: Carrier transporting layers
- H10K 50/155: comprising dopants
- H10K 50/165: comprising dopants
- Y10S 428/917: Electroluminescent
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

The present invention relates to an electronic device comprising at least one organic semiconducting material according to the following formula (I): wherein R1-4 are independently selected from H, halogen, CN, substituted or unsubstituted C1-C20-alkyl or heteroalkyl, C6-C20-aryl or C5-C20-heteroaryl, C1-C20-alkoxy or C6-C20-aryloxy, Ar is selected from substituted or unsubstituted C6-C20-aryl or C5-C20-heteroaryl, and R5 is selected from substituted or unsubstituted C6-C20-aryl or C5-C20-heteroaryl, H, F or formula (II).

## Claims

### Claim 1

An electronic device comprising at least one organic semiconducting material according to formula (I):
wherein R1-4 are independently selected from H, halogen, CN, C1-C20-alkyl, C1-C20-heteroalkyl, C6-C20-aryl, C5-C20-heteroaryl, C1-C20-alkoxy, or C6-C20-aryloxy, wherein each C1-C20-alkyl, C1-C20-heteroalkyl, C6-C20-aryl, C5-C20-heteroaryl, C1-C20 alkoxy, or C6-C20-aryloxy is unsubstituted or substituted,
wherein Ar is selected from, substituted or unsubstituted, C6-C20-aryl or C5-C20-heteroaryl, and
R5 is selected from substituted or unsubstituted C6-C20-aryl, substituted or unsubstituted C5-C20-heteroaryl, H, F, or
wherein R1-4, are as previously defined;
wherein the device has a layered structure and at least one layer comprises at least one compound according to formula (I).

### Claim 2 (depends on 1)

The electronic device according to claim 1, wherein Ar and R1-4 are independently selected from C6-C20 aryl or C5-C20-heteroaryl.

### Claim 3 (depends on 1)

The electronic device according to claim 1, wherein R5 is H or F, and R5 and Ar are a moiety selected from

### Claim 4 (depends on 1)

The electronic device according to claim 1, wherein Ar is selected from

### Claim 5 (depends on 1)

The electronic device according to claim 1, wherein the organic semiconducting material is doped by an n-dopant.

### Claim 6 (depends on 5)

The electronic device according to claim 5, wherein the organic semiconducting material is doped by an organic n-dopant having a HOMO energy level which is more positive than −3.3 eV.

### Claim 7 (depends on 1)

The electronic device according to claim 1, wherein the device is an electronic, optoelectronic or electroluminescent device having an electronically functionally effective region, wherein the electronically effective region comprises at least one compound according to formula (I).

### Claim 8 (depends on 1)

The electronic device according to claim 1, wherein the device is an organic light-emitting diode, a field-effect transistor, a sensor, a photodetector, an organic thin-film transistor, an organic integrated circuit, an organic light-emitting transistor, a light-emitting electrochemical cell, or an organic laser diode.

### Claim 9

A compound according to formula (I):
wherein R1-4 are independently selected from H, halogen, CN, C1-C20-alkyl, C1-C12-heteroalkyl, C6-C20-aryl, C5-C20-heteroaryl, C1-C20-alkoxy, or C6-C20aryloxy, wherein each C1-C20-alkyl, C1-C20-heteroalkyl, C1-C20-aryl, C5-C20-heteroaryl, C1-C20-alkoxy, or C6-C20-aryloxy is unsubstituted or substituted,
wherein R5 is H, and Ar is