Organic thin-film transistor and method for manufacturing the same, material for organic thin-film transistor, composition for organic thin-film transistor, compound, and organic semiconductor film

Patent metadata

Field	Value
Publication number	US-10629818-B2
Application number	US-201815885857-A
Country	US
Kind code	B2
Filing date	Feb 1, 2018
Priority date	Aug 4, 2015
Publication date	Apr 21, 2020
Grant date	Apr 21, 2020

Abstract

A compound which, when used for organic semiconductor films in organic thin-film transistors, makes the organic thin-film transistors exhibit a high carrier mobility, a material for an organic thin-film transistor for which the compound is used, a composition for an organic thin-film transistor, an organic thin-film transistor and a method for manufacturing the same, and an organic semiconductor film. The organic thin-film transistor contains a compound represented by General Formula (1) in an organic semiconductor film (organic semiconductor layer) thereof.

First claim

What is claimed is:

1. An organic thin-film transistor comprising:
an organic semiconductor film including a compound which is represented by General Formula (1) and has a molecular weight of 3,000 or less,

in General Formula (1), X represents an oxygen atom, a selenium atom, or a tellurium atom, R 1 to R 12 each independently represent a group represented by Formula (W), here, among R 1 to R 12 , at least one group is a group other than a hydrogen atom,
-L W -R W   (W)

in Formula (W), L W is a divalent linking group of any of a single bond, —O—, —S—, —NR 13 —, —CO—, —SO—, —SO 2 —, or —Si(R 14 )(R 15 ) or a divalent linking group obtained by bonding two or more divalent linking groups described above, R W represents a hydrogen atom or an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, all of which may have a substituent, and
R 13 to R 15 each independently represent a hydrogen atom or an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, all of which may have a substituent, wherein, in General Formula (1), the number of carbon atoms included in each of R 3 and R 10 is independently 1 to 30.

2. The organic thin-film transistor according to claim 1 ,
wherein, in General Formula (1), R 3 and R 10 each independently have, as R W , an alkyl group having 1 to 20 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms, all of which may have a substituent.

3. The organic thin-film transistor according to claim 1 ,
wherein, in General Formula (1), R 1 and R 12 are the same group, R 2 and R 11 are the same group, R 3 and R 10 are the same group, R 4 and R 9 are the same group, R 5 and R 8 are the same group, and R 6 and R 7 are the same group.

4. The organic thin-film transistor according to claim 1 ,
wherein X is a selenium atom.

5. The organic thin-film transistor according to claim 1 ,
wherein the compound is represented by General Formula (2),

R 3 to R 10 are the same group and each represent a group represented by Formula (W),
-L W -R W   (W)

in Formula (W), L W is a divalent linking group of any of a single bond, —O—, —S—, —NR 13 —, —CO—, —SO—, —SO 2 —, or —Si(R 14 )(R 15 ) or a divalent linking group obtained by bonding two or more divalent linking groups described above, R W represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms, all of which may have a substituent, and
R 13 to R 15 each independently represent a hydrogen atom or an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, all of which may have a substituent.

6. The organic thin-film transistor according to claim 5 ,
wherein, in General Formula (2), L W is a single bond.

7. The organic thin-film transistor according to claim 1 ,
wherein R 3 and R 10 each independently include a linear alkyl group.

8. A compound which is represented by General Formula (1) and has a molecular weight of 3,000 or less,

in General Formula (1), X represents an oxygen atom, a selenium atom, or a tellurium atom, R 1 to R 12 each independently represent a group represented by Formula (W), here, among R 1 to R 12 , at least one group is a group other than a hydrogen atom,
-L W -R W   (W)

in Formula (W), L W is a divalent linking group of any of a single bond, —O—, —S—, —NR 13 —, —CO—, —SO—, —SO 2 —, or —Si(R 14 )(R 15 ) or a divalent linking group obtained by bonding two or more divalent linking groups described above, R W represents a hydrogen atom or an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, all of which may have a substituent, and
R 13 to R 15 each independently represent a hydrogen atom or an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, all of which may have a substituent, wherein, in General Formula (1), the number of carbon atoms included in each of R 3 and R 10 is independently 1 to 30.

9. The compound according to claim 8 ,
wherein, in General Formula (1), R 3 and R 10 each independently have, as R W , an alkyl group having 1 to 20 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms, all of which may have a substituent.

10. The compound according to claim 8 ,
wherein, in General Formula (1), R 1 and R 12 are the same group, R 2 and R 11 are the same group, R 3 and R 10 are the same group, R 4 and R 9 are the same group, R 5 and R 8 are the same group, and R 6 and R 7 are the same group.

11. The compound according to claim 8 ,
wherein X is a selenium atom.

12. The compound according to claim 8 ,
wherein the compound is represented by General Formula (2),

in General Formulae (2), R 3 to R 10 are the same group and each represent a group represented by Formula (W),
-L W -R W   (W)

in Formula (W), L W is a divalent linking group of any of a single bond, —O—, —S—, —NR 13 —, —CO—, —SO—, —SO 2 —, or —Si(R 14 )(R 15 ) or a divalent linking group obtained by bonding two or more divalent linking groups described above, R W represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms, all of which may have a substituent, and
R 13 to R 15 each independently represent a hydrogen atom or an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, all of which may have a substituent.

13. The compound according to claim 12 ,
wherein, in General Formula (2), L W is a single bond.

14. The compound according to claim 8 ,
wherein R 3 and R 10 each independently include a linear alkyl group.

15. A material for an organic thin-film transistor comprising:
the compound according to claim 8 .

16. A composition for an organic thin-film transistor comprising:
the compound according to claim 8 ; and
a solvent.

17. A method for manufacturing an organic thin-film transistor comprising:
a step of forming an organic semiconductor film by applying the composition for an organic thin-film transistor according to claim 16 on a substrate and drying the composition.

18. An organic semiconductor film comprising:
the compound according to claim 8 .

Assignees

• Fujifilm Corp
• Univ Tokyo

Inventors

• Koyanagi Masashi
• Tsuyama Hiroaki
• Fukuzaki Eiji
• Usami Yoshihisa
• Watanabe Tetsuya
• Goto Takashi
• Okamoto Toshihiro
• Takeya Junichi

Classifications

• C07D421/14

  containing three or more hetero rings · CPC title

• C09D5/24

  Electrically-conducting paints {(conductive materials H01B1/00)} · CPC title

• C07D345/00

  Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms · CPC title

• H01B1/12

  organic substances {(organic macromolecular compounds or compositions C08)} · CPC title

• H01L51/0004

  Electricity · mapped topic