Field effect transistor

Patent metadata

Field	Value
Publication number	US-9796727-B2
Application number	US-201013203494-A
Country	US
Kind code	B2
Filing date	Feb 25, 2010
Priority date	Feb 27, 2009
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

A heterocyclic compound represented by formula (1) and a field effect transistor having a semiconductor layer comprising the compound. (In the formula, X 1 and X 2 each independently represents a sulfur atom or a selenium atom, and R 1 and R 2 each independently represents a C 5-16 alkyl.)

First claim

The invention claimed is:

1. A heterocyclic compound represented by the following Formula (1):

wherein X 1 and X 2 each independently represent a sulfur atom or a selenium atom, and R 1 and R 2 each independently represent a C6-C14 alkyl group.

2. The heterocyclic compound according to claim 1 , wherein R 1 and R 2 of Formula (1) each independently represent a linear C6-C14 alkyl group.

3. The heterocyclic compound according to claim 1 , wherein R 1 and R 2 of Formula (1) each independently represent a branched C6-C14 alkyl group.

4. The heterocyclic compound according to claim 1 , wherein each of X 1 and X 2 of Formula (1) represents a sulfur atom.

5. A method for producing an intermediate compound represented by Formula (B) in producing a heterocyclic compound represented by the following Formula (1), comprising the steps of:
mixing a compound represented by Formula (A) with an alkyl metal reagent such as butyllithium; and
further adding dimethyl disulfide, or selenium and methyl iodide thereto:

wherein X 1 and X 2 each independently represent a sulfur atom or a selenium atom, and R 1 and R 2 each independently represent a C6-C14 alkyl group;

wherein X represents a sulfur atom or a selenium atom, and R represents a C6-C14 alkyl group.

6. A method for producing the heterocyclic compound represented by the following Formula (1) according to claim 1 , comprising the steps of:
reacting intermediates represented by Formula (B) with one another to produce a compound represented by Formula (C); and
subsequently reacting the compound represented by Formula (C) with iodine:

wherein X 1 and X 2 each independently represent a sulfur atom or a selenium atom, and R 1 and R 2 each independently represent a C6-C14 alkyl group;

wherein X represents a sulfur atom or a selenium atom, and R represents a C6-C14 alkyl group;

wherein X 1 and X 2 each independently represent a sulfur atom or a selenium atom, and R 1 and R 2 each independently represent a C6-C14 alkyl group.

7. An organic semiconductor material comprising at least one heterocyclic compound according to claim 1 .

8. An ink for use in producing a semiconductor device, comprising the heterocyclic compound according to claim 1 .

9. A field effect transistor having a semiconductor layer comprising at least one heterocyclic compound represented by the following Formula (1):

wherein X 1 and X 2 each independently represent a sulfur atom or a selenium atom, and R 1 and R 2 each independently represent a C6-C14 alkyl group.

10. The field effect transistor according to claim 9 , wherein the field effect transistor is of bottom-contact type.

11. The field effect transistor according to claim 9 , wherein the field effect transistor is of top-contact type.

12. The field effect transistor according to any one of claims 9 to 11 , further comprising a gate electrode, a gate insulating film, a source electrode, and a drain electrode, wherein the gate insulating film is an organic insulating film.

13. A method for producing a field effect transistor, comprising the step of forming a semiconductor layer comprising at least one heterocyclic compound represented by the following Formula (1) on a substrate:

wherein X 1 and X 2 each independently represent a sulfur atom or a selenium atom, and R 1 and R 2 each independently represent a C6-C14 alkyl group.

14. The method for producing the field effect transistor according to claim 13 , wherein the semiconductor layer is formed by a vapor deposition method.

15. The method for producing the field effect transistor according to claim 13 , wherein the semiconductor layer is formed by applying the heterocyclic compound represented by the following Formula (1) dissolved in an organic solvent:

wherein X 1 and X 2 each independently represent a sulfur atom or a selenium atom, and R 1 and R 2 each independently represent a C6-C14 alkyl group.

16. The method for producing the field effect transistor according to any one of claims 13 to 15 , wherein the semiconductor layer is heat-treated, after the semiconductor layer is formed.

17. A fine particle of the heterocyclic compound represented by Formula (1) according to claim 1 .

18. The fine particle according to claim 17 , wherein the average particle diameter is 5 nm or more and 50 μm or less.

19. A method for producing the fine particle according to claim 17 or 18 , wherein the fine particle is precipitated by cooling a solution of the heterocyclic compound dissolved in an organic solvent or by mixing the solution with a solvent.

20. The method for producing the fine particle according to claim 17 or 18 , wherein the fine particle is precipitated by mixing a solution of the heterocyclic compound dissolved in an organic solvent with a polar solvent.

21. The method for producing the fine particle according to claim 19 , wherein the organic solvent for dissolving the heterocyclic compound has a boiling point of 100° C. or more.

22. A dispersion of the fine particle of the heterocyclic compound, wherein the fine particle according to claim 17 or 18 is dispersed in a solvent.

23. A method for producing the dispersion according to claim 22 , wherein the method comprises the step of dispersing the fine particle in a solvent by mechanical stress.

24. An ink for use in producing a semiconductor device, comprising the dispersion according to claim 22 .

25. A method for producing a field effect transistor comprising a step of forming a semiconductor layer by applying the ink for use in producing the semiconductor device according to claim 24 .

26. The method for producing the field effect transistor according to claim 25 , wherein the semiconductor layer is heat-treated, after the semiconductor layer is formed.

27. The heterocyclic compound according to claim 1 , wherein R 1 and R 2 of Formula (1) each independently represent a linear C6-C12 alkyl group.

28. The method for producing a field effect transistor according to claim 5 , wherein R 1 and R 2 of Formula (1) each independently represent a linear C6-C12 alkyl group.

Assignees

• Kuwabara Hirokazu
• Ikeda Masaaki
• Takimiya Kazuo
• Nippon Kayaku Kk

Inventors

• Kuwabara Hirokazu
• Ikeda Masaaki
• Takimiya Kazuo

Classifications

• C07C319/14

  of sulfides · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• H01L51/0005

  Electricity · mapped topic

• H01L51/0074

  Electricity · mapped topic

• C07C323/22

  containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title