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, and organic semiconductor film for non-light-emitting organic semiconductor device

Patent metadata

Field	Value
Publication number	US-9705095-B2
Application number	US-201615199138-A
Country	US
Kind code	B2
Filing date	Jun 30, 2016
Priority date	Jan 9, 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; 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; and an organic semiconductor film for a non-light-emitting organic semiconductor device (each of X 1 and X 2 represents NR 13 , an O atom, or a S atom; A 1 represents CR 7 or a N atom; A 2 represents CR 8 or a N atom; R 13 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an acyl group; each of R 1 to R 8 independently represents a hydrogen atom or a substituent; at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , or R 8 is a substituent represented by -L-R; L represents a divalent linking group having a specific structure; and R represents an alkyl group, a cyano group, a vinyl group, an ethynyl group, an oxyethylene group, an oligo-oxyethylene group in which a repetition number v of an oxyethylene unit is equal to or greater than 2, a siloxane group, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group).

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 and X 2 independently represents NR 13 , an O atom, or a S atom,
A 1 represents CR 7 or a N atom, A 2 represents CR 8 or a N atom,
R 13 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 8 independently represents a hydrogen atom or a substituent, and at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , or R 8 is a substituent represented by the following Formula (W):
-L-R  Formula (W)

in Formula (W), 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 one of the following Formulae (L-1) to (L-25) are bonded to each other, and
R represents a substituted or unsubstituted alkyl group, a cyano group, a vinyl group, an ethynyl group, an oxyethylene group, an oligo-oxyethylene group in which a repetition number v of an oxyethylene unit is equal to or greater than 2, a siloxane group, an oligosiloxane group having two or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group;

in Formulae (L-1) to (L-25), the portion of a wavy line represents a position of bonding to a phenanthrene skeleton condensed with two 5-membered heterocyclic rings,
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 and X 2 independently represents an O atom or a S atom,
A 1 represents CR 7 or a N atom, A 2 represents CR 8 or a N atom,
each of R 1 to R 5 , R 7 , and R 8 independently represents a hydrogen atom or a substituent, R 5 is not a group represented by -L a -R a ,
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, and
R a represents a substituted or unsubstituted alkyl group, a cyano group, a vinyl group, an ethynyl group, an oxyethylene group, an oligo-oxyethylene group in which a repetition number v of an oxyethylene unit is equal to or greater than 2, an oligosiloxane group having two or more silicon atoms, a siloxane group, or a substituted or unsubstituted trialkylsilyl group;

in Formula (2-2),
each of X 1 and X 2 independently represents an O atom or a S atom,
A 1 represents CR 7 or a N atom, A 2 represents CR 8 or a N atom,
each of R 1 to R 4 , R 7 , and R 8 independently represents a hydrogen atom or a substituent,
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, and
each of R b and R c independently represents a substituted or unsubstituted alkyl group, a cyano group, a vinyl group, an ethynyl group, an oxyethylene group, an oligo-oxyethylene group in which a repetition number v of an oxyethylene unit is equal to or greater than 2, a siloxane group, an oligosiloxane group having two or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group;

in Formulae (L-1) to (L-25), the portion of a wavy line represents a position of bonding to a phenanthrene skeleton condensed with two 5-membered heterocyclic rings,
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 in the Formula (1), A 1 is CR 7 or A 2 is CR 8 , and each of R 7 and R 8 independently represents a hydrogen atom or a substituent.

4. The organic transistor according to claim 1 ,
wherein in the Formula (1), at least one of X 1 or X 2 is a S atom.

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), (L-13), (L-17), and (L-18) or a divalent linking group in which two or more divalent linking groups represented by any of the above formulae are bonded to each other.

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-1), (L-3), (L-13), and (L-18) or a divalent linking group in which a divalent linking group represented by any one of the Formulae (L-3), (L-13), and (L-18) 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 a substituted or unsubstituted alkyl group.

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

in Formula (1),
each of X 1 and X 2 independently represents NR 13 , an O atom, or a S atom,
A 1 represents CR 7 or a N atom, A 2 represents CR 8 or a N atom,
R 13 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 8 independently represents a hydrogen atom or a substituent, and at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , or R 8 is a substituent represented by the following Formula (W):
-L-R  Formula (W)

in Formula (W), 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

Assignees

• Fujifilm Corp

Inventors

• Youfu Katsuyuki
• Hirai Yuki
• Masui Kensuke

Classifications

• C07D498/04

  Ortho-condensed systems · CPC title

• H01L51/0545

  Electricity · mapped topic

• H01L51/0566

  Electricity · mapped topic

• C07D513/04

  Ortho-condensed systems · CPC title

• C07C2103/26

  Chemistry & Metallurgy · mapped topic