Compound and application thereof

Patent metadata

Field	Value
Publication number	US-12358926-B2
Application number	US-202017800692-A
Country	US
Kind code	B2
Filing date	Feb 19, 2020
Priority date	Feb 19, 2020
Publication date	Jul 15, 2025
Grant date	Jul 15, 2025

Abstract

Provided is a compound that is excellent in chemical stability, has high solubility in a solvent, and exhibits excellent carrier mobility.
A compound represented by Formula (1):

where in Formula (1), X 1 , X 2 , X 3 , and R 1 to R 10 are as defined in the specification.

First claim

The invention claimed is:

1. A compound represented by Formula (1):

where in Formula (1), X 1 is an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom; X 2 and X 3 , which may be the same or different, are each a carbon atom, an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom, with the proviso that a case of X 2 and X 3 being simultaneously carbon atoms is excluded; R 1 and R 2 , which may be the same or different, are each a hydrogen atom or an organic group, and R 3 to R 10 , which may be the same or different, are each a hydrogen atom, a halogen atom, or an organic group; R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 , and R 9 and R 10 may each bond to each other to form a ring; and a double line including a dashed line represents a single bond or a double bond.

2. The compound according to claim 1 , represented by Formula (1′):

wherein in Formula (1′), X 1 , X 2 and X 3 are the same as those in Formula (1); R 1′ and R 2′ are the same or different organic groups; and a double line including a dashed line represents a single bond or a double bond.

3. The compound according to claim 2 , wherein, in Formula (1′), X 1 is a sulfur atom; one of X 2 and X 3 is a carbon atom and the other is a sulfur atom; and R 1′ and R 2′ are the same or different organic groups.

4. A method of manufacturing the compound described in claim 1 , comprising obtaining a compound represented by Formula (1-5) from a compound represented by Formula (1-4):

wherein in Formulas (1-4) and (1-5), X 1 , X 2 , X 3 , and the double line including a dashed line indicate the same contents as those of Formula (1).

5. An organic semiconductor solution composition comprising the compound described in claim 1 and at least one solvent.

6. An organic semiconductor film formed from the organic semiconductor solution composition described in claim 5 .

7. An organic thin film transistor comprising the organic semiconductor film described in claim 6 .

8. The compound according to claim 1 , wherein X 1 is a sulfur atom.

9. The compound according to claim 1 , wherein X 2 is a sulfur atom and X 3 is a carbon atom.

10. The compound according to claim 1 , wherein the organic groups according to R 1 and R 2 are alkyl groups having from 1 to 40 carbon atom(s).

11. The compound according to claim 1 , wherein the organic groups in R 1 and R 2 are the same and linear or branched alkyl groups having from 1 to 20 carbon atom(s).

12. The compound according to claim 3 , represented by Formula (1″):

where in Formula (1″), R 1′ and R 2′ are the same or different organic groups; and a double line including a dashed line represents a single bond or a double bond.

13. The compound according to claim 12 , wherein the organic groups in R 1′ and the R 2′ are alkyl groups having from 1 to 40 carbon atom(s).

14. The compound according to claim 12 , wherein the organic groups in R 1′ and R 2′ are the same and linear or branched alkyl groups having from 1 to 20 carbon atom(s).

15. A method of manufacturing the compound described in claim 2 , comprising obtaining a compound represented by Formula (1-5) from a compound represented by Formula (1-4):

wherein in Formulas (1-4) and (1-5), X 1 , X 2 , X 3 , and the double line including a dashed line indicate the same contents as those of Formula (1).

16. An organic semiconductor solution composition comprising the compound described in claim 12 and at least one solvent.

17. An organic semiconductor film formed from the organic semiconductor solution composition described in claim 16 .

18. An organic thin film transistor comprising the organic semiconductor film described in claim 17 .

Assignees

• Daicel Corp
• Univ Tokyo

Inventors

• Ikeda Daiji
• Yokoo Takeshi
• Akai Yasuyuki
• Okamoto Toshihiro
• KUROSAWA Tadanori
• Takeya Junichi
• Cen Dinghai

Classifications

• H10K10/484

  characterised by the channel regions · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D495/14 Primary

  Ortho-condensed systems · CPC title