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

Patent metadata

Field	Value
Publication number	US-9714253-B2
Application number	US-201514632741-A
Country	US
Kind code	B2
Filing date	Feb 26, 2015
Priority date	Aug 27, 2012
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

An organic thin film transistor having a semiconductor active layer containing a compound represented by the formula (1) has a high carrier mobility and a small change in the threshold voltage after repeated operation. R 1 to R 10 represent H or a substituent, provided that at least one of R 1 to R 4 and R 6 to R 9 represents a substituent represented by -L-R, L represents a specific divalent linking group, and R represents an alkyl group, an oligooxyethylene group, an oligosiloxane group, or a trialkylsilyl group.

First claim

What is claimed is:

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

wherein in the general formula (1), R 1 to R 10 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 4 and R 6 to R 9 represents a substituent represented by the following general formula (W), and in the general formula (W), when L represents a divalent linking group represented solely by the following general formula (L-1), at least two of R 1 to R 4 and R 6 to R 9 each represent a substituent represented by the following general formula (W), and the substituents represented by R 1 to R 4 and R 6 to R 9 do not form a condensed ring by being bonded to each other,
-L-R  General Formula (W)

wherein in the general formula (W), L represents a divalent linking group represented by one of the following general formulae (L-1) to (L-13) or a divalent linking group containing two or more of divalent linking groups represented by any of the following general formulae (L-1) to (L-13) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 2 or more carbon atoms, an oligooxyethylene group having a number of repetition of oxyethylene units of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group, provided that R is capable of representing a substituted or unsubstituted trialkylsilyl group only in the case where L adjacent to R represents a divalent linking group represented by the following general formula (L-3):

wherein in the general formulae (L-1) to (L-13), a position shown by a wave line represents a bonding position to the benzobisbenzofuran skeleton; a position shown by * represents the bonding position to R in the general formula (W); n in the general formula (L-1) represents an integer of 1 or more; m in the general formula (L-10) represents 4; m in the general formulae (L-11) and (L-12) represents 2; and R′ in the general formulae (L-1), (L-2), (L-10), (L-11), (L-12) and (L-13) each independently represent a hydrogen atom or a substituent,
wherein the compound represented by the general formula (1) is a compound represented by one of the following general formulae (2-3) and (2-4):

wherein in the general formula (2-3), L e represents a divalent linking group represented by the following general formula (L-3′); R e represents a substituted or unsubstituted alkyl group having 2 or more carbon atoms, an oligooxyethylene group having a number of repetition of oxyethylene units of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group; R 31 and R 32 each independently represent a substituent (provided that R 31 is not a group represented by the general formula (W)); R 5 and R 10 each independently represent a hydrogen atom or a substituent; n31 represents an integer of from 0 to 4; and n32 represents an integer of from 0 to 3,

wherein in the general formula (2-4), L f represents a divalent linking group represented by the following general formula (L-3′); R f represents a substituted or unsubstituted alkyl group having 2 or more carbon atoms, an oligooxyethylene group having a number of repetition of oxyethylene units of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group; R 41 and R 42 each independently represent a substituent (provided that R 41 and R 42 are not a group represented by the general formula (W)); R 5 and R 10 each independently represent a hydrogen atom or a substituent; n41 represents an integer of from 0 to 4; and n42 represents an integer of from 0 to 3:

wherein in the general formula (L-3′) in the general formulae (2-3) and (2-4), a position shown by a wave line represents a bonding position to the benzobisbenzofuran skeleton; a position shown by * represents the bonding position to one of R e and R f adjacent to the general formula (L-3′).

2. The organic thin film transistor according to claim 1 , wherein in the general formula (2-3) or (2-4), R e and R f each independently represent an alkyl group.

3. The organic thin film transistor according to claim 1 , wherein in the general formula (2-3) or (2-4), R e represents an alkyl group having from 2 to 12 carbon atoms; and R f represents an alkyl group having from 2 to 12 carbon atoms.

4. A compound represented by one of the following general formulae (2-3′) or (2-4′):

wherein in the general formula (2-3′), L e represents a divalent linking group represented by the following general formula (L-3′); R e represents a substituted or unsubstituted alkyl group having from 2 to 12 carbon atoms, an oligooxyethylene group having a number of repetition of oxyethylene units of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group; R 31 and R 32 each independently represent a substituent (provided that R 31 is not a group represented by the following general formula (W)); R 5 and R 10 each independently represent a hydrogen atom or a substituent; n31 represents an integer of from 0 to 4; and n32 represents an integer of from 0 to 3,

wherein in the general formula (2-4′), L f represents a divalent linking group represented by the following general formula (L-3′); R f represents a substituted or unsubstituted alkyl group having from 2 to 12 carbon atoms, an oligooxyethylene group having a number of repetition of oxyethylene units of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group; R 41 and R 42 each independently represent a substituent (provided that R 41 and R 42 are not a group represented by the following general formula (W)); R 5 and R 10 each independently represent a hydrogen atom or a substituent; n41 represents an integer of from 0 to 4; and n42 represents an integer of from 0 to 3:

wherein in the general formula (L-3′) a position shown by a wave line represents a bonding position to the benzobisbenzofuran skeleton; a position shown by * represents the bonding position to one of R e and R f adjacent to the general formula (L-3′);
-L-R  General Formula (W)

wherein in the general formula (W), L represents a divalent linking group represented by one of the following general formulae (L-1) to (L-13) or a divalent linking group containing two or more of divalent linking groups represented by any of the following general formulae (L-1) to (L-13) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 2 or more carbon atoms, an oligooxyethylene group having a number of repetition of oxyethylene units of 2 or more, an oligosiloxane group having 2 or more silicon atoms, or a substituted or unsubstituted trialkylsilyl group, provided that R is capable of representi

Assignees

• Fujifilm Corp

Inventors

• Kitamura Tetsu
• Takaku Koji
• Sotoyama Wataru
• Hirai Yuki
• Kinoshita Masaru
• SHIGENOI Yuuta

Classifications

• H01L51/0065

  Electricity · mapped topic

• C07F7/0852

  Chemistry & Metallurgy · mapped topic

• C07F7/0812

  comprising a heterocyclic ring · CPC title

• H01L51/0062

  Electricity · mapped topic

• H01L51/0545

  Electricity · mapped topic