Organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, coating solution for non-light-emitting organic semiconductor device, organic semiconductor film for non-light-emitting organic semiconductor device, and method for manufacturing organic semiconductor film for non-light emitting organic semiconductor device

Patent metadata

Field	Value
Publication number	US-9705096-B2
Application number	US-201615203506-A
Country	US
Kind code	B2
Filing date	Jul 6, 2016
Priority date	Jan 10, 2014
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

Provided are an organic transistor having high carrier mobility that contains a compound represented by the following formula in a semiconductor active layer (each of X 1 to X 4 represents NR 100 , an O atom, or a S atom; NR 100 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an acyl group, an aryl group, or a heteroaryl group; each of R 1 to R 6 represents a hydrogen atom or a substituent; at least one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 is a substituent represented by -L-R; L is a divalent linking group having a specific structure; and R is an alkyl group having 5 to 19 carbon atoms); a compound; an organic semiconductor material for a non-light-emitting organic semiconductor device; a material for an organic transistor; a coating solution for a non-light-emitting organic semiconductor device; an organic semiconductor film for a non-light-emitting organic semiconductor device; and a method for manufacturing an organic semiconductor film for a non-light-emitting organic semiconductor device.

First claim

What is claimed is:

1. An organic transistor comprising a compound represented by the following Formula (1) in a semiconductor active layer;

in Formula (1),
each of X 1 to X 4 independently represents NR 100 , an O atom, or a S atom,
R 100 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an acyl group, an aryl group, or a heteroaryl group,
each of R 1 to R 6 independently represents a hydrogen atom or a substituent, and at least one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 is a substituent represented by the following Formula (W):
-L-R  Formula (W)

in Formula (W),
R represents an alkyl group having 5 to 19 carbon atoms, and
L represents a divalent linking group represented by any of the following Formulae (L-1) to (L-25) or a divalent linking group in which two or more divalent linking groups represented by any of the following Formulae (L-1) to (L-25) are bonded to each other;

in Formulae (L-1) to (L-25), the portion of a wavy line represents a position of bonding to a condensed heterocyclic skeleton,
m in Formula (L-13) represents 4, m in Formulae (L-14) and (L-15) represents 3, m in Formulae (L-16) to (L-20) represents 2, m in Formula (L-22) represents 6,
each R′ in Formulae (L-1), (L-2), (L-6), and (L-13) to (L-24) independently represents a hydrogen atom or a substituent,
R N represents a hydrogen atom or a substituent, and
each R si independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

2. The organic transistor according to claim 1 ,
wherein the compound represented by the Formula (1) is a compound represented by the following Formula (2-1) or (2-2);

in Formula (2-1),
each of X 1 to X 4 independently represents an O atom or a S atom,
each of R 1 to R 3 , R 4A , and R 5 independently represents a hydrogen atom or a substituent and is not a group represented by -L a -R a ,
R a represents an alkyl group having 5 to 19 carbon atoms, and
L a represents a divalent linking group represented by any of the following Formulae (L-1) to (L-25) or a divalent linking group in which two or more divalent linking groups represented by any of the following Formulae (L-1) to (L-25) are bonded to each other;

in Formula (2-2),
each of X 1 to X 4 independently represents an O atom or a S atom,
each of R 1 , R 2 , R 3C , and R 4B independently represents a hydrogen atom or a substituent,
each of R b and L c independently represents an alkyl group having 5 to 19 carbon atoms, and
each of L b and L c independently represents a divalent linking group represented by any of the following Formulae (L-1) to (L-25) or a divalent linking group in which two or more divalent linking groups represented by any of the following Formulae (L-1) to (L-25) are bonded to each other;

in Formulae (L-1) to (L-25), the portion of a wavy line represents a position of bonding to a condensed heterocyclic skeleton,
m in Formula (L-13) represents 4, m in Formulae (L-14) and (L-15) represents 3, m in Formulae (L-16) to (L-20) represents 2, m in Formula (L-22) represents 6,
each R′ in Formulae (L-1), (L-2), (L-6), and (L-13) to (L-24) independently represents a hydrogen atom or a substituent,
R N represents a hydrogen atom or a substituent, and
each R si independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

3. The organic transistor according to claim 1 ,
wherein the compound represented by the Formula (1) is a compound represented by the following Formula (2-2A);

in Formula (2-2A),
each of X 1 to X 4 independently represents an O atom or a S atom,
each of R 1 and R 2 independently represents a hydrogen atom or a substituent,
each of R b and R c independently represents an alkyl group having 5 to 19 carbon atoms, and
each of L b and L c independently represents a divalent linking group represented by any of the following Formulae (L-1) to (L-25) or a divalent linking group in which two or more divalent linking groups represented by any of the following Formulae (L-1) to (L-25) are bonded to each other;

in Formulae (L-1) to (L-25), the portion of a wavy line represents a position of bonding to a condensed heterocyclic skeleton,
m in Formula (L-13) represents 4, m in Formulae (L-14) and (L-15) represents 3, m in Formulae (L-16) to (L-20) represents 2, m in Formula (L-22) represents 6,
each R′ in Formulae (L-1), (L-2), (L-6), and (L-13) to (L-24) independently represents a hydrogen atom or a substituent,
R N represents a hydrogen atom or a substituent, and
each R si independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

4. The organic transistor according to claim 1 ,
wherein in the Formula (1), L is a divalent linking group represented by any of the Formulae (L-1) to (L-5) and (L-13) to (L-24) or a divalent linking group in which two or more divalent linking groups represented by any of the Formulae (L-1) to (L-5) and (L-13) to (L-24) are bonded to each other.

5. The organic transistor according to claim 1 ,
wherein in the Formula (1), L is a divalent linking group represented by any of the Formulae (L-1) to (L-5) and (L-13) to (L-24), or a divalent linking group in which a divalent linking group represented by any one of the Formulae (L-2), (L-3), and (L-13) to (L-24) or a divalent linking group, in which two or more divalent linking groups represented by any of the Formulae (L-2), (L-3), and (L-13) to (L-24) are bonded to each other, is bonded to a divalent linking group represented by the Formula (L-1).

6. The organic transistor according to claim 1 ,
wherein in the Formula (1), L is a divalent linking group represented by any of the Formulae (L-2), (L-3), (L-14) to (L-21), (L-23), and (L-24) or a divalent linking group in which a divalent linking group, in which two or more divalent linking groups represented by any of the Formulae (L-2), (L-3), (L-14) to (L-21), (L-23), and (L-24) are bonded to each other, is bonded to a divalent linking group represented by the Formula (L-1).

7. The organic transistor according to claim 1 ,
wherein in the Formula (1), R is an unsubstituted alkyl group.

8. The organic transistor according to cla

Assignees

• Fujifilm Corp

Inventors

• Youfu Katsuyuki
• Hirai Yuki
• Masui Kensuke

Classifications

• H01L51/0065

  Electricity · mapped topic

• C07D495/04

  Ortho-condensed systems · CPC title

• H01L51/0068

  Electricity · mapped topic

• H01L51/0074 Primary

  Electricity · mapped topic

• C07D495/22

  in which the condensed system contains four or more hetero rings · CPC title