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

Patent metadata

Field	Value
Publication number	US-9711733-B2
Application number	US-201514816517-A
Country	US
Kind code	B2
Filing date	Aug 3, 2015
Priority date	Feb 4, 2013
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

An organic thin film transistor containing a compound represented by one of the following formulae in a semiconductor active layer has a high carrier mobility and a small change in the threshold voltage after repeated driving. X represents S or O, and at least one of R 1 to R 6 represents -L-R wherein L represents alkylene, etc., and R represents alkyl, etc.

First claim

What is claimed is:

1. An organic thin film transistor containing a compound represented by the following formula (1-1) or (1-2) in a semiconductor active layer:

wherein in the formulae (1-1) and (1-2), X represents a S atom or an O atom; and R 1 to R 6 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 6 represents a substituent represented by the following formula (W):
-L-R  Formula (W)

wherein in the formula (W), L represents 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, an oligooxyethylene group having a repeating number v of an oxyethylene unit of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group, provided that the substituted or unsubstituted alkyl group represented by R has a number of carbon atoms in the main chain thereof of 3 or more in the case where L represents a divalent linking group represented by the formula (L-1), 2 or more in the case where L represents a divalent linking group represented by the formula (L-2) or (L-3), or 4 or more in the case where L represents a divalent linking group represented by any one of the formulae (L-4) to (L-12), and R represents a substituted or unsubstituted trialkylsilyl group only in the case where L adjacent to R represents a divalent linking group represented by the formula (L-3):

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthothiazole or naphthoxazole skeleton; in the formula (L-10), m represents 4, in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-1), (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 5 and R 6 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 (1-1) or (1-2) is a compound represented by the following formula (2-1) or (2-2):

wherein in the formula (2-1), R 1 to R 4 each independently represent a hydrogen atom or a substituent; L a and L b each independently represent 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, an oligooxyethylene group having a repeating number v of an oxyethylene unit of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group, provided that the substituted or unsubstituted alkyl groups represented by R a and R b each have a number of carbon atoms in the main chain thereof of 3 or more in the case where L a and L b respectively represent a divalent linking group represented by the formula (L-1), 2 or more in the case where L a and L b respectively represent a divalent linking group represented by the formula (L-2) or (L-3), or 4 or more in the case where L a and L b respectively represent a divalent linking group represented by any one of the formulae (L-4) to (L-12), and R a and R b each represent a substituted or unsubstituted trialkylsilyl group only in the case where L a and L b adjacent to R a and R b respectively represent a divalent linking group represented by the formula (L-3),

wherein in the formula (2-2), R 1 to R 4 independently represent a hydrogen atom or a substituent; L c and L d each independently represent 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, an oligooxyethylene group having a repeating number v of an oxyethylene unit of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group, provided that the substituted or unsubstituted alkyl groups represented by R c and R d each have a number of carbon atoms in the main chain thereof of 3 or more in the case where L c and L d respectively represent a divalent linking group represented by the formula (L-1), 2 or more in the case where L c and L d respectively represent a divalent linking group represented by the formula (L-2) or (L-3), or 4 or more in the case where L c and L d respectively represent a divalent linking group represented by any one of the formulae (L-4) to (L-12), and R c and R d each represent a substituted or unsubstituted trialkylsilyl group only in the case where L c and L d adjacent to R c and R d respectively represent a divalent linking group represented by the formula (L-3):

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthothiazole or naphthoxazole skeleton; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-1), (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 1 , wherein in the formula (W), R represents a substituted or unsubstituted alkyl group, an oligooxyethylene group having a repeating number v of an oxyethylene unit of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group, provided that the substituted or unsubstituted alkyl group represented by R has a number of carbon atoms in the main chain thereof of 4 or more in the case where L represents a divalent linking group represented by any one of the formulae (L-1) and (L-4) to (L-12),or 2 or more in the case where L represents a divalent linking group represented by the formula (L-2) or (L-3), and R represents a substituted or unsubstituted trialkylsilyl group only in the case where L adjacent to R represents a divalent linking group represented by the formula (L-3).

5. The organic thin film transistor according to claim 3 , wherein in the formula (2-1) or (2-2), R 1 to R 4 each independently represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms, a substituted or unsubstituted alkynyl group having from 2 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 12 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 12 carbon atoms, or a substituted or unsubstituted alkylthio group having from 1 to 12 carbon atoms.

6. The organic thin film transistor according to claim 3 , wherein in the formula (2-1) or (2-2), al

Assignees

• Fujifilm Corp

Inventors

• Takaku Koji
• Yonekuta Yasunori
• Sotoyama Wataru
• Kinoshita Masaru

Classifications

• H01L51/0068

  Electricity · mapped topic

• C07F7/0849

  Chemistry & Metallurgy · mapped topic

• H01L51/0065

  Electricity · mapped topic

• H01L51/0035

  Electricity · mapped topic

• C08K5/47

  Thiazoles · CPC title