Photosensitive composition and organic thin-film transistor

Patent metadata

Field	Value
Publication number	US-2019250509-A1
Application number	US-201916269096-A
Country	US
Kind code	A1
Filing date	Feb 6, 2019
Priority date	Feb 9, 2018
Publication date	Aug 15, 2019
Grant date	—

Abstract

A photosensitive composition comprising a polymer compound composed of a repeating unit represented by the following formula (1) and at least one repeating unit selected from the group consisting of a repeating unit represented by the following formula (2), a repeating unit represented by the following formula (3) and a repeating unit represented by the following formula (4), and a compound having at least two azide groups:

In the formula (1), Ar 1 represents a phenyl group or a naphthyl group, and in the formula (2), Ar 2 represents a phenyl group or a naphthyl group. l, m, n1 and n2 are numbers satisfying l≥15 and m+n1+n2=100-l, and 1+n2≥10 when the total amount of all repeating units contained in the above-described polymer compound is taken as 100.

First claim

1 . A photosensitive composition comprising a polymer compound composed of a repeating unit represented by the following formula (1) and at least one repeating unit selected from the group consisting of a repeating unit represented by the following formula (2), a repeating unit represented by the following formula (3) and a repeating unit represented by the following formula (4), and a compound having at least two azide groups:

wherein, in the formula (1), Ar 1 represents a phenyl group or a naphthyl group,
R a is a group represented by the following formula (5); when a plurality of R a are present, they may be the same or different and may be combined together to form a ring together with a carbon atom on Ar 1 to which they are attached,
R b is a hydrogen atom, a fluorine atom, a phenyl group optionally having a substituent, a naphthyl group optionally having a substituent or a group represented by the following formula (6); when a plurality of R b are present, they may be the same or different,
when Ar 1 is a phenyl group, i represents an integer of 1 to 5 and j represents an integer of 5-i,
when Ar 1 is a naphthyl group, i represents an integer of 1 to 7 and j represents an integer of 7-i,
X 1 represents a hydrogen atom or a methyl group,
R c represents a divalent organic group having a number of carbon atoms of 1 to 20, a group represented by —O— or a group represented by —C(═O)—, and
k represents an integer of 0 to 6;
in the formula (2), Ar 2 represents a phenyl group or a naphthyl group,
a plurality of R d are each a hydrogen atom, a fluorine atom, a phenyl group optionally having a substituent, a naphthyl group optionally having a substituent or a group represented by the following formula (6), a plurality of R d may be the same or different,
when Ar 2 is a phenyl group, p represents 5,
when Ar 2 is a naphthyl group, p represents 7,
X 2 represents a hydrogen atom or a methyl group,
R e represents a divalent organic group having a number of carbon atoms of 1 to 20, a group represented by —O— or a group represented by —C(═O)—, and
q represents an integer of 0 to 6;
in the formula (3), R 2 1 , R 2 2 and R 2 3 are each independently a hydrogen atom, a fluorine atom or an alkyl group having a number of carbon atoms of 1 to 20, and R 2 1 , R 2 2 , R 2 3 and Z may be combined together to form a ring,
Z represents an alkyl group having a number of carbon atoms of 1 to 20 or an alkenyl group having a number of carbon atoms of 2 to 20,
A hydrogen atom contained in the group represented by Z may be substituted with a fluorine atom,
R h represents a divalent organic group having a number of carbon atoms of 1 to 20, a group represented by —O— or a group represented by —C(═O)—, and
r represents an integer of 0 to 6;
in the formula (4), R 2 4 and R 2 5 each independently represent a hydrogen atom or an alkyl group having a number of carbon atoms of 1 to 20,
l, m, n1 and n2 are numbers satisfying l≥15 and m+n1+n2=100-l, and l+n2≥10 when the total amount of all repeating units contained in said polymer compound is taken as 100:

wherein, in the formula (5), R f and R g are each independently a hydrogen atom, a fluorine atom or a hydrocarbon group optionally substituted with a fluorine atom, and R f and R g may be combined together to form a ring:

wherein, in the formula (6), X 3 , X 4 and X 5 are each independently a fluorine atom or a hydrocarbon group optionally substituted with a fluorine atom.

2 . The photosensitive composition according to claim 1 , wherein in said polymer compound, Ar 1 in the repeating unit represented by the formula (1) is a phenyl group.

3 . The photosensitive composition according to claim 1 , wherein in said polymer compound, Ar 2 in the repeating unit represented by the formula (2) is a phenyl group.

4 . The photosensitive composition according to claim 1 , wherein in said repeating unit represented by the formula (1), the group represented by R a is a methyl group.

5 . The photosensitive composition according to claim 1 , wherein in said repeating unit represented by the formula (1), k is 0.

6 . The photosensitive composition according to claim 1 , wherein in said repeating unit represented by the formula (3), r is 0 to 3.

7 . The photosensitive composition according to claim 1 , wherein said compound having at least two azide groups is a compound represented by the following formula (7):

wherein, in the formula (7),
R 1 to R 8 each independently represent a hydrogen atom, a fluorine atom, an alkyl group having a number of carbon atoms of 1 to 5, an alkoxy group having a number of carbon atoms of 1 to 5 or a group represented by SO 3 M, wherein M represents a hydrogen atom, an alkali metal atom, an alkyl group having a number of carbon atoms of 1 to 10 or NR A R B , and R A and R B each independently represent a hydrogen atom, an alkyl group having a number of carbon atoms of 1 to 10, a hydroxyalkyl group having a number of carbon atoms of 1 to 10, an alkoxyalkyl group having a number of carbon atoms of 1 to 10 or a hydroxyalkoxyalkyl group having a number of carbon atoms of 1 to 10, and
Y represents a single bond, a group represented by —C(═O)—, a group represented by —S—, an alkylene group having a number of carbon atoms of 1 to 8 or a divalent group represented by any one of the following formula (7-1) to the following formula (7-4), wherein in the formula (7-4), R 9 is a hydrogen atom or an alkyl group having a number of carbon atoms of 1 to 10:

8 . An ink comprising the photosensitive composition according to claim 1 and an organic solvent.

9 . A film obtained by hardening the photosensitive composition according to claim 1 .

10 . An electronic device comprising the film according to claim 9 .

11 . An organic thin-film transistor comprising the film according to claim 9 as an insulation layer.

12 . An organic thin-film transistor comprising the film according to claim 9 as a gate insulation layer.

13 . A production method of a hardened film, comprising
a step of applying the ink according to claim 8 on an object to obtain a film, a step of heating said film to remove the organic solvent, and a step of exposing said organic solvent-removed film.

14 . A production method of an organic thin-film transistor having an insulation layer, a source electrode, a drain electrode, a gate electrode and an organic semiconductor layer, comprising
a step of forming an insulation layer composed of the hardened film obtained by the production method according to claim 13 , a step of forming a source electrode, a drain electrode and a gate electrode, and a step of forming an organic semiconductor layer.

Assignees

• Sumitomo Chemical Co

Inventors

• Okachi Takayuki
• Yoshikawa Eiji

Classifications

• G03F7/0048

  characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents · CPC title

• G03F7/008 Primary

  Azides (G03F7/075 takes precedence) · CPC title

• G03F7/0125

  characterised by the polymeric binder or the macromolecular additives other than the macromolecular azides · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• G03F7/012 Primary

  Macromolecular azides; Macromolecular additives, e.g. binders {(G03F7/0085 takes precedence)} · CPC title