Photocrosslinkable polymer, insulating film, planarization film, lyophilic/liquid repellent patterned film, and organic field effect transistor device comprising same

Patent metadata

Field	Value
Publication number	US-12291587-B2
Application number	US-201816494107-A
Country	US
Kind code	B2
Filing date	Mar 9, 2018
Priority date	Mar 16, 2017
Publication date	May 6, 2025
Grant date	May 6, 2025

Abstract

Provided is a resin which is excellent in terms of solubility in common solvents, crosslinking temperature, time required for crosslinking, solvent resistance (cracking resistance), breakdown voltage, leakage current, solvent wettability, and planarity in cases where the resin is formed into a thin film. A resin which comprises repeating units represented by formula (1) and formula (2), and wherein the repeating unit represented by formula (2) is contained in an amount of 20% by mole or more relative to the total amount of the repeating units represented by formula (1) and formula (2).

First claim

The invention claimed is:

1. A resin, consisting of:
a plurality of repeating units represented by the following formula (1);
a plurality of repeating units represented by the following formula (2),
wherein the resin comprises from 20% to 91% by mole of the repeating units represented by the formula (2) with respect to a total amount of the repeating units represented by the formulae (1) and (2):

wherein in the formula (1), R 1 represents hydrogen or a C1-C6 alkyl group; S 1 represents —O— or —C(O)—; p represents 0; A 1 represents a C6-C19 aryl group; Y represents halogen, a cyano group, a carboxyalkyl group, an alkyl ether group, an aryl ether group, a C1-C18 alkyl group, a fluoroalkyl group, or a cycloalkyl group; and k represents 0, wherein s represents the number of carbon atoms constituting the A 1 ,

wherein in the formula (2), R 2 represents hydrogen or a C1-C6 alkyl group; S 2 represents —O— or —C(O)—; q represents 0; A 2 represents a C6-C19 aryl group; Y represents a substituent as defined in formula (1); j represents 0 and m represents 1,
wherein r represents the number of carbon atoms constituting the A 2 ; and Z represents at least one organic group selected from the formulae (A) to (D):

wherein in the formulae (A) to (D), R 3 and R 4 each independently represents hydrogen; and R 5 to R 29 independently represent hydrogen; and
further optionally,
a plurality of repeating units represented by the following formula (18);
a plurality of repeating units represented by the following formula (19); or
a combination thereof,

wherein R 2 , S 2 , A 2 , and Y each represent a substituent defined in the formula (2),
q represents an integer defined in the formula (2),
n represents an integer from 0 to (t-4),
t represents the total number of the carbon atoms constituting A 2 ,
d and e represent single bonds that are located in the ortho positions to each other (bonded to adjacent carbons) on the aromatic group A 2 , and
R 3 to R 9 are the same as those defined in the formula (A), and

Z is the formula (A);

wherein A 3 represents a C6-C19 aryl group,
Y represents substituent defined in the formula (1),
R 30 represents hydrogen or a C1-C6 alkyl group,
R f represents a C1-C18 fluoroalkyl group,
v represents an integer from 0 to (u-2),
w represents an integer from 1 to (u-v-1), and
u represents the number of carbon atoms constituting A 3 .

2. An insulating film, comprising:
a crosslinked product of the resin according to claim 1 .

3. An organic field effect transistor device, comprising:
a substrate;
an organic semiconductor layer;
a gate electrode; and
the gate insulating layer comprising the insulating film of claim 2 ,
wherein, on the substrate, the organic semiconductor layer and the gate electrode are stacked to each other via the gate insulating layer, and
a source electrode and a drain electrode are attached on the organic semiconductor layer.

4. A planarization film comprising the resin according to claim 1 and/or a crosslinked product of the resin according to claim 1 .

5. A lyophilic/liquid-repellent patterned film comprising the resin according to claim 1 and/or a crosslinked product of the resin according to claim 1 .

6. A film, comprising:
the resin of claim 1 ;
wherein the film is a planarization film.

7. A film, comprising:
the resin of claim 1 ; and
a crosslinked product of the resin of claim 1 ,
wherein the film is a lyophilic/liquid-repellent patterned film.

8. The resin of claim 1 , wherein the organic group of the formula (A) is one of followings:

9. The resin of claim 1 , wherein R 30 in the formula (19) is the C1-C6 alkyl group which is one of a methyl group, an ethyl group, a n-propyl group, an isopropyl group, and a n-butyl group.

10. A film, comprising:
the resin of claim 9 ,
wherein the film is a lyophilic/liquid-repellent patterned film.

11. A film, comprising:
a crosslinked product of the resin of claim 9 ,
wherein the film is a lyophilic/liquid-repellent patterned film.

12. A film, comprising:
the resin of claim 9 ; and
a crosslinked product of the resin of claim 9 ,
wherein the film is a lyophilic/liquid-repellent patterned film.

13. A film, comprising:
the resin of claim 1 ,
wherein the film is a lyophilic/liquid-repellent patterned film.

14. A film, comprising:
a crosslinked product of the resin of claim 1 ,
wherein the film is a lyophilic/liquid-repellent patterned film.

15. A film, comprising:
a crosslinked product of the resin of claim 1 ,
wherein the film is a planarization film.

Assignees

• Tosoh Corp

Inventors

• Yamakawa Hiroshi
• OKU Shinya
• Yumino Shohei
• LEE Junghwi
• Katagiri Fumiaki

Classifications

• C08F212/02

  Monomers containing only one unsaturated aliphatic radical · CPC title

• H10K10/471

  the gate dielectric comprising only organic materials · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/151

  Copolymers · CPC title

• H10K85/111

  comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene · CPC title