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-9620723-B2
Application number	US-201213728313-A
Country	US
Kind code	B2
Filing date	Dec 27, 2012
Priority date	Sep 5, 2008
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

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 represented by a following formula:

Ar 1 represents an unsubstituted aryl group having 6 to 13 carbon atoms or aryl group having 6 to 13 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms;
Ar 2 represents an unsubstituted aryl group having 6 to 13 carbon atoms or aryl group having 6 to 13 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 13 carbon atoms;
R 1 to R 4 each independently represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, or halogen; and
Ar 1 and a carbon of α are bonded to each other directly or through sulfur, oxygen, or nitrogen.

2. The compound according to claim 1 ,
wherein:
the compound is represented by a following formula:

R 11 to R 15 each independently represent any of hydrogen or alkyl group having 1 to 4 carbon atoms;
R 16 to R 20 each independently represent any of hydrogen, alkyl group having 1 to 4 carbon atoms, or an unsubstituted aryl group having 6 to 13 carbon atoms; and
an ortho-carbon with respect to the nitrogen atom in the above formula, which is directly bonded to R 11 , and a carbon of α are bonded to each other directly or through sulfur, oxygen, or nitrogen.

3. A compound represented by a following formula:

Ar 11 represents an unsubstituted aryl group having 6 to 13 carbon atoms or aryl group having 6 to 13 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms;
Ar 12 represents an unsubstituted aryl group having 6 to 13 carbon atoms or aryl group having 6 to 13 carbon atoms substituted by an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 13 carbon atoms; and
Ar 13 represented by any one of following formulae:

and
Ar 11 and a carbon of α are bonded to each other directly or through any of oxygen, sulfur, or nitrogen.

4. The compound according to claim 3 ,
wherein:
the compound is represented by a following formula:

R 31 to R 35 represent any of hydrogen or an alkyl group having 1 to 4 carbon atoms;
R 36 to R 40 each independently represent any of hydrogen, alkyl group having 1 to 4 carbon atoms, or an unsubstituted aryl group having 6 to 13 carbon atoms; and
an ortho-carbon with respect to the nitrogen atom in the above formula, which is directly bonded to R 31 , and a carbon of α are bonded to each other directly or through sulfur, oxygen, or nitrogen.

5. A light-emitting element comprising a compound according to claim 1 between a pair of electrodes.

6. A lighting device comprising the light-emitting element according to claim 5 .

7. An electric device having a display portion, the display portion comprising the light-emitting element according to claim 5 .

8. A light-emitting element comprising a compound according to claim 3 between a pair of electrodes.

9. A lighting device comprising the light-emitting element according to claim 8 .

10. An electric device having a display portion, the display portion comprising the light-emitting element according to claim 8 .

11. The compound according to claim 1 , wherein Ar 1 is represented by any one of the following formulae:

12. The compound according to claim 11 , wherein Ar 2 is represented by any one of the following formulae:

13. The compound according to claim 1 , wherein R 1 to R 4 each is independently represented by any one of the following formulae:

14. The compound according to claim 2 , wherein R 1 to R 4 each is independently represented by any one of the following formulae:

15. The compound according to claim 14 , wherein R 16 to R 20 each is independently represented by any one of the following formulae:

16. The compound according to claim 3 , wherein Ar 11 is represented by any one of the following formulae:

17. The compound according to claim 16 , wherein Ar 12 is represented by any one of the following formulae:

18. The compound according to claim 4 , wherein R 32 to R 35 each is independently represented by any one of the following formulae:

19. The compound according to claim 18 , wherein R 36 to R 40 each is independently represented by any one of the following formulae:

Assignees

• Semiconductor Energy Lab

Inventors

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

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C07D271/07

  with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical · CPC title

• C07D413/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title