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

Patent metadata

Field	Value
Publication number	US-9447111-B2
Application number	US-201514685894-A
Country	US
Kind code	B2
Filing date	Apr 14, 2015
Priority date	Oct 15, 2012
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

An organic thin film transistor containing a compound represented by the formula (1) in a semiconductor active layer has a high carrier mobility and a small fluctuation of the threshold voltage after repeated driving. R 1 to R 12 represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the formula (W), or all of R 1 to R 12 represent a hydrogen atom. * represents a position bonded to the naphthobisbenzofuran skeleton. L represents a single bond, a divalent linking group, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms.

First claim

What is claimed is:

1. An organic thin film transistor containing a compound represented by the following formula (1) in a semiconductor active layer:

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:
*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

2. The organic thin film transistor according to claim 1 , wherein at least one of R 2 , R 3 , R 8 and R 9 represents a substituent represented by the formula (W).

3. The organic thin film 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):

wherein R 1 , R 3 to R 7 , and R 9 to R 12 each independently represent a hydrogen atom or a substituent; L a and L b each independently represent a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R a and R b each independently represent a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms,

wherein R 1 , R 2 , R 4 to R 8 , and R 10 to R 12 each independently represent a hydrogen atom or a substituent; L c and L d each independently represent a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R c and R d each independently represent a substituted or unsubstituted alkyl group having 6 to 12carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms,

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

4. The organic thin film transistor according to claim 3 , wherein in the formula (2-1) or (2-2), R a , R b , R c and R d represent an alkyl group having 6 to 12 carbon atoms.

5. The organic thin film transistor according to claim 3 , wherein in the formula (2-1) or (2-2), R a , R b , R c and R d represent a linear alkyl group having from 6 to 12carbon atoms.

6. The organic thin film transistor according to claim 3 , wherein in formula (2-1) or (2-2), L a , L b , L c and L d represent a single bond.

7. An organic semiconductor material for a non-light emitting organic semiconductor device, containing the compound represented by the following formula (1):

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:
*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

8. A material for an organic thin film transistor, containing the compound represented by the following formula (1):

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:
*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in

Assignees

• Fujifilm Corp

Inventors

• Kitamura Tetsu
• Takaku Koji
• Sotoyama Wataru

Classifications

• H01L51/0094

  Electricity · mapped topic

• H01L51/0061

  Electricity · mapped topic

• C07F7/0852

  Chemistry & Metallurgy · mapped topic

• H01L51/006

  Electricity · mapped topic

• H01L51/0035

  Electricity · mapped topic