Organic semiconductor material, organic semiconductor thin film, and organic thin film transistor

Patent metadata

Field	Value
Publication number	US-9133193-B2
Application number	US-201013502262-A
Country	US
Kind code	B2
Filing date	Oct 29, 2010
Priority date	Oct 29, 2009
Publication date	Sep 15, 2015
Grant date	Sep 15, 2015

Abstract

Provided are an organic semiconductor material, organic semiconductor thin film and organic thin-film transistor, which contain a perylene tetracarboxylic diimide derivative represented by the following formula (1):

In the formula (1), R 1 means a linear or branched alkyl group having from 1 to 20 carbon atoms, R 2 means a linear or branched alkyl group having from 2 to 6 carbon atoms, R 3 means a linear or branched alkyl group having from 2 to 6 carbon atoms, X 1 and X 2 each mean a heteroatom selected from an oxygen atom, sulfur atom or selenium atom, Y means a halogen atom or cyano group, m stands for a number of from 0 to 4, and n stands for a number of from 0 to 2. Further, the alkyl groups represented by R 1 and R 2 may each be substituted with one or more fluorine atoms.

First claim

The invention claimed is:

1. An organic semiconductor material comprising a perylene tetracarboxylic diimide derivative represented by following formula (1):

wherein R 1 is a linear alkyl group having from 8 to 20 carbon atoms,
R 2 is a linear alkyl group having from 2 to 6 carbon atoms,
R 3 is a linear alkyl group having from 2 to 6 carbon atoms,
X 1 and X 2 are each oxygen,
Y is halogen or a cyano group,
m stands for a number from 0 to 4,
n stands for a number from 0 to 2,
wherein the material is soluble in an organic solvent, and
the material forms a thin film having a transistor performance by a printing method or a solution coating method when dissolved in the organic solvent.

2. The organic semiconductor material according to claim 1 ,
wherein the derivative represented by the formula (1) is an N,N′-bis(3-(R 1 -oxy)-ethyl)-3,4:9,10-perylene tetracarboxylic diimide derivative represented by following formula (2):

wherein R 1 is a linear alkyl group having from 8 to 20 carbon atoms.

3. The organic semiconductor material according to claim 1 ,
wherein the derivative represented by the formula (1) is an N,N′-bis(3-(R 1 -oxy)-n-propyl)-3,4:9,10-perylene tetracarboxylic diimide derivative represented by following formula (3):

wherein R 1 is a linear alkyl group having from 8 to 20 carbon atoms.

4. The organic semiconductor material according to claim 3 ,
wherein the derivative represented by the formula (3) is N,N′-bis(3-(n-dodecyloxy)-n-propyl)-3,4:9,10-perylene tetracarboxylic diimide represented by following formula (4):

wherein the —C 12 H 25 group in the formula (4) is a n-dodecyl group.

5. An organic semiconductor thin film comprising the organic semiconductor material according to claim 1 .

6. An organic semiconductor thin film comprising the organic semiconductor material according to claim 1 ,
wherein the organic semiconductor material has a temperature of a phase transition into a liquid crystal state in a range from 100° C. to 250° C.

7. An organic thin-film transistor; which is formed on a substrate and comprises: a gate electrode; a gate insulating layer; an organic semiconductor thin film; a source electrode; and a drain electrode,
wherein the organic semiconductor thin film comprises the organic semiconductor thin film according to claim 5 .

8. An organic thin-film transistor, which is formed on a substrate and comprises: a gate electrode; a gate insulating layer; an organic semiconductor thin film; a source electrode; and a drain electrode,
wherein the organic semiconductor thin film comprises the organic semiconductor thin film according to claim 6 , and
the organic semiconductor thin film is a film having been treated with heat at a temperature between 100° C. and 250° C.

9. The organic thin-film transistor according to claim 7 , which has an electron mobility from 0.01 to 5.0 cm 2 /Vs.

Assignees

• Ichikawa Musubu
• Hirata Naoki
• Kono Hisao
• Oguma Naomi
• Dainichiseika Color Chem
• Univ Shinshu

Inventors

• Ichikawa Musubu
• Hirata Naoki
• Kono Hisao
• Oguma Naomi

Classifications

• H01L51/0053

  Electricity · mapped topic

• H01L51/0545

  Electricity · mapped topic

• C07D471/06 Primary

  Peri-condensed systems · CPC title

• C09B5/62

  Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series · CPC title

• H10K10/466

  Lateral bottom-gate IGFETs comprising only a single gate · CPC title