Organic thin film transistor

Patent metadata

Field	Value
Publication number	US-9899605-B2
Application number	US-201514865649-A
Country	US
Kind code	B2
Filing date	Sep 25, 2015
Priority date	Mar 27, 2013
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

An organic thin film transistor containing a compound represented by the formula (1) in a semiconductor active layer has a high carrier mobility, a small change in the threshold voltage after repeated driving and a high solubility in an organic solvent. A 1 and A 2 represent S, O or Se; at least one of R 1 to R 6 represents a substituent represented by *-L-R wherein L represents a divalent linking group and R represents a hydrogen atom, an alkyl group, an oligooxyethylene group, an oligosiloxane group or a trialkylsilyl group.

First claim

What is claimed is:

1. A compound represented by the following formula (1):

wherein in the formula (1), A 1 and A 2 each independently represent a sulfur atom, an oxygen atom or a selenium 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), * represents a position bonded to a naphthalene ring in the formula (1), or bonded to a ring containing A 1 or a ring containing A 2 ; L represents a divalent linking group represented by any one of the following formulae (L-1) to (L-10), or a divalent linking group consisting of 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-10) in which the 2 or more divalent linking groups are bonded sequentially; and R represents a hydrogen atom, a substituted or unsubstituted alkyl group, an oligooxyethylene group having a repeating number 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 R represents a hydrogen atom only when L is represented by any one of the formulae (L-1) to (L-3) and (L-8) to (L-10), and R represents a substituted or unsubstituted trialkylsilyl group only when L bonded to R is a divalent linking group represented by the following formula (L-3);

wherein in the formulae (L-1) to (L-10), the wavy line represents a position bonded to any one of a naphthalene ring, a ring containing A 1 and a ring containing A 2 ; and * represents a position bonded to R in the formula (W); in the formula (L-8), m represents 4; in the formulae (L-9) and (L-10), m represents 2; in the formulae (L-1), (L-2), (L-8), (L-9) and (L-10), R′ each independently represents a hydrogen atom or a substituent, provided that, in the formulae (L-1) and (L-2), R′ each independently may form a condensed ring with R bonded to L.

2. The compound according to claim 1 , wherein at least one of R 1 and R 2 in the formula (1) represents a substituent represented by the formula (W).

3. The compound according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (2):

wherein in the formula (2), A 1 and A 2 each independently represent a sulfur atom, an oxygen atom or a selenium atom; R 2 to R 6 each independently represent a hydrogen atom or a substituent; L a represents a divalent linking group represented by any one of the following formulae (L-1) to (L-10), or a divalent linking group consisting of 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-10) in which the 2 or more divalent linking groups are bonded sequentially; and R a represents a hydrogen atom, a substituted or unsubstituted alkyl group, an oligooxyethylene group having a repeating number 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 R a represents a hydrogen atom only when L a is represented by any one of the formulae (L-1) to (L-3) and (L-8) to (L-10), and R a represents a substituted or unsubstituted trialkylsilyl group only when L a bonded to R a is a divalent linking group represented by the following formula (L-3);

wherein in the formulae (L-1) to (L-10), the wavy line represents a position bonded to any one of a naphthalene ring, a ring containing A 1 and a ring containing A 2 ; and * represents a position bonded to R a ; in the formula (L-8), m represents 4; in the formulae (L-9) and (L-10), m represents 2; in the formulae (L-1), (L-2), (L-8), (L-9) and (L-10), R′ each independently represents a hydrogen atom or a substituent, provided that, in the formulae (L-1) and (L-2), R′ each independently may form a condensed ring with R bonded to L.

4. The compound according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (3):

wherein in the formula (3), A 1 and A 2 each independently represent a sulfur atom, an oxygen atom or a selenium atom; R 3 to R 6 each independently represent a hydrogen atom or a substituent; L b and L c each independently represent a divalent linking group represented by any one of the following formulae (L-1) to (L-10), or a divalent linking group consisting of 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-10) in which the 2 or more divalent linking groups are bonded sequentially; and R b and R c each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, an oligooxyethylene group having a repeating number 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 R b and R c represent a hydrogen atom only when L b and L c are represented by any one of the formulae (L-1) to (L-3) and (L-8) to (L-10), and R b and R c represent a substituted or unsubstituted trialkylsilyl group only when L b and L c each bonded to R b and R c are a divalent linking group represented by the following formula (L-3);

wherein in the formulae (L-1) to (L-10), the wavy line represents a position bonded to any one of a naphthalene ring, a ring containing A 1 and a ring containing A 2 ; and * represents a position bonded to R b or R c ; in the formula (L-8), m represents 4; in the formulae (L-9) and (L-10), m represents 2; in the formulae (L-1), (L-2), (L-8), (L-9) and (L-10), R′ each independently represents a hydrogen atom or a substituent, provided that, in the formulae (L-1) and (L-2), R′ each independently may form a condensed ring with R bonded to L.

5. The compound according to claim 1 , wherein R 3 to R 6 in the formula (1) each independently represent a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having from 1 to 3 carbon atoms, a substituted or unsubstituted alkynyl group having from 2 to 3 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 3 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 2 carbon atoms, or a substituted or unsubstituted methylthio group.

6. The compound according to claim 3 , wherein all of L a in the formula (2) each represent a divalent linking group represented by any one of the formulae (L-1) to (L-3), (L-8), (L-9) or (L-10).

7. The compound according to claim 3 , wherein all of L a in the formula (2) each represent a divalent linking group represented by any one of the formula (L-1) or (L-8).

8. The compound according to claim 3 , wherein all of R a in the formula (2) each represent a substituted or unsubstituted alkyl group.

9. The compound according to claim 3 , wherein all of R a in the formula (2) each represent a linear alkyl group.

10. The compound according to claim 1 , wherein the compound represented by the formula

Assignees

• Fujifilm Corp

Inventors

• Yonekuta Yasunori
• Takaku Koji
• Sotoyama Wataru

Classifications

• C07F7/0849

  Chemistry & Metallurgy · mapped topic

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• H01L51/0068

  Electricity · mapped topic

• H01L51/0094

  Electricity · mapped topic

• C07D513/06

  Peri-condensed systems · CPC title