Condensed polycyclic aromatic compound and use thereof

Patent metadata

Field	Value
Publication number	US-9859508-B2
Application number	US-201414771213-A
Country	US
Kind code	B2
Filing date	Feb 27, 2014
Priority date	Feb 28, 2013
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

[Problem] To provide: a novel compound which has high mobility and on/off ratio and is useful for organic electronic devices; and a method for producing the compound.
[Solution] A condensed polycyclic aromatic compound which is represented by general formula (1). (In the formula, A represents a 1,5-dihydronaphthalene ring or a 2,6-dihydronaphthalene ring; each of R 1 , R 2 , R 3 and R 4 independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted hydrocarbon oxy group, a substituted or unsubstituted ester group, a substituted or unsubstituted acyl group, or a substituted or unsubstituted cyano group; and each of X 1 and X 2 independently represents an oxygen atom, a sulfur atom or a selenium atom.)

First claim

The invention claimed is:

1. A condensed polycyclic aromatic compound represented by general formula (1):

wherein A represents a 1,5-dihydronaphthalene ring or a 2,6-dihydronaphthalene ring; R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted hydrocarbon oxy group, a substituted or unsubstituted ester group, a substituted or unsubstituted acyl group or a substituted or unsubstituted cyano group; and X 1 and X 2 each independently represent an oxygen atom, a sulfur atom or a selenium atom.

2. The condensed polycyclic aromatic compound according to claim 1 , wherein X 1 and X 2 are sulfur atoms.

3. The condensed polycyclic aromatic compound according to claim 1 , wherein R 3 and R 4 are hydrogen atoms.

4. The condensed polycyclic aromatic compound according to claim 1 , wherein R 1 and R 2 are each an aliphatic hydrocarbon group having 1 to 30 carbon atoms.

5. The condensed polycyclic aromatic compound according to claim 4 , wherein R 1 and R 2 are each a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

6. An organic semiconductor material comprising the condensed polycyclic aromatic compound according to any one of claims 1 to 5 .

7. The organic semiconductor material according to claim 6 , wherein the organic semiconductor material is a transistor material.

8. A composition for forming a thin film comprising the condensed polycyclic aromatic compound according to any one of claims 1 to 5 , and an organic solvent.

9. The composition for forming a thin film according to claim 8 , wherein the content of the condensed polycyclic aromatic compound is in the range of 0.01 part by weight or higher and 10 parts by weight or lower relative to 100 parts by weight of the organic solvent.

10. A thin film comprising the condensed polycyclic aromatic compound according to any one of claims 1 to 5 .

11. An organic semiconductor device comprising the thin film according to claim 10 .

12. The organic semiconductor device according to claim 11 , wherein the device is an organic transistor device.

13. A method for producing an organic semiconductor device, comprising a step of applying the composition for forming a thin film according to claim 8 onto a substrate by a solution process.

14. A method for producing an organic semiconductor device, comprising a step of applying the composition for forming a thin film according to claim 9 onto a substrate by a solution process.

Assignees

• Nippon Kayaku Kk

Inventors

• Takimiya Kazuo
• SHINAMURA Shoji
• Hamada Masahiro
• Sadamitsu Yuichi

Classifications

• H01L51/0558

  Electricity · mapped topic

• H01L51/0051

  Electricity · mapped topic

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• H01L51/0074 Primary

  Electricity · mapped topic