Organic semiconductor material and light-emitting element, light-emitting device, lighting system, and electronic device using the same

Patent metadata

Field	Value
Publication number	US-10243151-B2
Application number	US-201715477847-A
Country	US
Kind code	B2
Filing date	Apr 3, 2017
Priority date	Sep 5, 2008
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

Disclosed is a novel organic semiconductor material which has a twisted quaterphenylene skeleton as a central unit and simultaneously possesses a skeleton having an electron-transporting property and a skeleton having a hole-transporting property at the terminals of the quaterphenylene skeleton. Specifically, the organic semiconductor material has a [1,1′:2′,1″:2″,1′″]quaterphenyl-4-4′″-diyl group, and one of the terminals of the [1,1′:2′,1″:2″,1′″]quaterphenyl-4-4′″-diyl group is bonded to a skeleton having an electron-transporting property such as a benzoxazole group or an oxadiazole group. A skeleton having a hole-transporting property such as diarylamino group is introduced at the other terminal. This structure allows the formation of a compound having a bipolar property, a high molecular weight, an excellent thermal stability, a large band gap, and high triplet excitation energy.

First claim

The invention claimed is:

1. A compound having the following formula:

wherein:
any one of R 1 to R 4 is any of an alkyl group having 1 to 4 carbon atoms, an unsubstituted aryl group having 6 to 10 carbon atoms or halogen; the others of R 1 to R 4 independently are any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an unsubstituted aryl group having 6 to 10 carbon atoms or halogen; and
R 92 and R 93 independently are hydrogen, or an alkyl group having 1 to 6 carbon atoms.

2. The compound according to claim 1 ,
wherein R 92 and R 93 each are an alkyl group and bonded to each other.

3. The compound according to claim 1 , wherein the others of R 1 to R 4 are independently any one of the following formulae:

4. A compound having the following formula:

wherein Ar 1 and Ar 2 are independently any one of the following formulae:

5. The compound according to claim 4 , wherein the compound has the following formula:

6. A compound having the following formula:

wherein:
R 1 to R 4 independently are any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an unsubstituted aryl group having 6 to 10 carbon atoms or halogen; and
R 92 and R 93 are hydrogen.

7. The compound according to claim 6 , wherein R 1 to R 4 are independently any one of the following formulae:

Assignees

• Semiconductor Energy Lab

Inventors

• Seo Satoshi
• Kawakami Sachiko
• Nomura Hiroko
• Ohsawa Nobuharu

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C07D413/10

  linked by a carbon chain containing aromatic rings · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title

• C09K2211/1011

  Condensed systems · CPC title