Photosensitive resin composition, polyamide resin, method for producing polyamide resin, compound, method for producing compound, method for producing cured film, and cured film

Patent metadata

Field	Value
Publication number	US-10527940-B2
Application number	US-201715699292-A
Country	US
Kind code	B2
Filing date	Sep 8, 2017
Priority date	Sep 13, 2016
Publication date	Jan 7, 2020
Grant date	Jan 7, 2020

Abstract

A photosensitive resin composition capable of forming a cured film with satisfactory adhesion to substrates and excellent transparency, a polyamide resin which is used in the photosensitive resin composition, a method for producing the polyamide resin, a compound which is used as a raw material of the polyamide resin, a method for producing the compound, a method for producing a cured film using the photosensitive resin composition, and a cured film which is obtained by curing the photosensitive resin composition. The photosensitive resin composition including a resin and a photopolymerization initiator. The resin is a polyamide resin including a structural unit, which includes a specific saturated alicyclic skeleton, and at least one carboxy group esterified by a unit containing a polymerizable group of a predetermined structure.

First claim

What is claimed is:

1. A photosensitive resin composition comprising a resin (A) and a photopolymerization initiator (B), wherein the resin (A) is a polyamide resin including a structural unit represented by the following formula (a1):

wherein, in the formula (a1), X 1 is a tetravalent group represented by the following formula (a2):

Y 1 is a divalent organic group,
R a1 and R a2 each independently represents a hydrogen atom, a saturated aliphatic hydrocarbon group having 1 or more and 20 or less carbon atoms, an aryl group having 6 or more and 20 or less carbon atoms, an aralkyl group having 7 or more and 20 or less carbon atoms, or a group represented by the following formula (a3):

at least one of R a1 and R a2 is a group represented by the above formula (a3),
in the formula (a2), R a3 , R a4 , and R a5 each independently represents one selected from the group consisting of a hydrogen atom, an alkyl group having 1 or more and 10 or less carbon atoms, and
a fluorine atom,
n is an integer of 0 or more and 12 or less,
in the above formula (a3), R a6 , R a7 , and R a8 each independently represents a hydrogen atom or an organic group having 1 or more and 3 or less carbon atoms, and
m is an integer of 2 or more and 10 or less.

2. The photosensitive resin composition according to claim 1 , wherein the polyamide resin is a condensate of a polyvalent carboxylic acid compound represented by the following formula (I):

wherein, in the formula (I), X 1 is R a1 , and R a2 is the same as defined in the formula (a1), and/or an acid halide of the polyvalent carboxylic acid compound with a diamine compound represented by the following formula (II):
H 2 N—Y 1 —NH 2   (II)

wherein, in the formula (II), Y 1 is as the same as defined in the formula (a1).

3. The photosensitive resin composition according to claim 1 , further comprising a photopolymerizable monomer (C).

4. The photosensitive resin composition according to claim 1 , wherein the polyamide resin has a weight average molecular weight of 50,000 or less.

5. A method for producing a cured film, the method comprising:
applying the photosensitive resin composition according to claim 1 to form a coating film; and
exposing the coating film to an active energy ray.

6. The method for producing a cured film according to claim 5 , wherein exposure of the coating film is regioselectively performed, and the method further comprises developing the exposed coating film.

7. A cured film which is obtained by curing the photosensitive resin composition according to claim 1 .

8. A polyamide resin comprising a structural unit represented by the following formula (a1):

wherein, in the formula (a1), X 1 is a tetravalent group represented by the following formula (a2):

Y 1 is a divalent organic group,
R a1 and R a2 each independently represents a hydrogen atom, a saturated aliphatic hydrocarbon group having 1 or more and 20 or less carbon atoms, an aryl group having 6 or more and 20 or less carbon atoms, an aralkyl group having 7 or more and 20 or less carbon atoms, or a group represented by the following formula (a3):

at least one of R a1 and R a2 is a group represented by the formula (a3),
in the above formula (a2), R a3 , R a4 , and R a5 each independently represents one selected from the group consisting of a hydrogen atom, an alkyl group having 1 or more and 10 or less carbon atoms, and a fluorine atom,
n is an integer of 0 or more and 12 or less,
in the above formula (a3), R a6 , R a7 , and R a8 each independently represents a hydrogen atom or an organic group having 1 or more and 3 or less carbon atoms,
m is an integer of 2 or more and 10 or less, wherein —COOR a1 or —COOR a2 of the structural unit (a1) may be replaced with —COX a1 or —COX a2 , respectively, wherein X a1 and X a2 are halogen atoms, to form an acid halide, or —COOR a1 or —COOR a2 of the structural unit (a1) may be replaced with —COOY a1 or —COOY a2 , respectively, wherein Y a1 and Y a2 are cations, to form a carboxylate salt.

9. The polyamide resin according to claim 8 , which is a condensate of a polyvalent carboxylic acid compound represented by the following formula (I):

wherein, in the formula (I), X 1 , R a1 , and R a2 are the same as defined in the formula (a1),
wherein —COOR a1 or —COOR a2 of the polyhydric carboxylic acid compound (I) may be replaced with —COX a1 or —COX a2 , respectively , wherein X a1 and X a2 are halogen atoms, to form an acid halide, or —COOR a1 or —COOR a2 of the polyhydric carboxylic acid compound (I) may be replaced with —COOY a1 or —COOY a2 , respectively, wherein Y a1 and Y a2 are cations, to form a carboxylate salt,
and a diamine compound represented by the following formula (II):
H 2 N—Y 1 —NH 2   (II)

wherein, in the formula (II), Y 1 is the same as defined in the formula (a1).

10. The polyamide resin according to claim 8 , wherein the weight average molecular weight is 50,000 or less.

11. A method for producing the polyamide resin according to claim 8 , the method comprising condensing a polyvalent carboxylic acid compound represented by the following formula (I):

wherein, in the formula (I), X 1 is a tetravalent group represented by the following formula (a2):

R a1 and R a2 each independently represents a hydrogen atom, a saturated aliphatic hydrocarbon group having 1 or more and 20 or less carbon atoms, an aryl group having 6 or more and 20 or less carbon atoms, an aralkyl group having 7 or more and 20 or less carbon atoms, or a group represented by the following formula (a3):

at least one of R a1 and R a2 is a group represented by the formula (a3),
in the formula (a2), R a3 , R a4 , R a5 each independently represents one selected from the group consisting of a hydrogen atom, an alkyl group having 1 or more and 10 or less carbon atoms, and
a fluorine atom,
n is an integer of 0 or more and 12 or less,
in the formula (a3), R a6 , R a7 , and R a8 each independently represents a hydrogen atom or an organic group having 1 or more and 3 or less carbon atoms,
m is an integer of 2 or more and 10 or less, and/or
an acid halide of the polyvalent carboxylic acid compound, with
a diamine compound represented by the following formula (II):
H 2 N—Y 1 —NH 2   (II)

wherein, in the formula (II)

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Tadokoro Yoshinori
• Shiota Dai

Classifications

• G03F7/037

  the binders being polyamides or polyimides · CPC title

• G03F7/0388

  with ethylenic or acetylenic bands in the side chains of the photopolymer · CPC title

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• C08G73/14

  Polyamide-imides · CPC title

• C07C2603/94

  containing "free" spiro atoms · CPC title