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-2019332012-A9
Application number	US-201715699292-A
Country	US
Kind code	A9
Filing date	Sep 8, 2017
Priority date	Sep 13, 2016
Publication date	Oct 31, 2019
Grant date	—

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 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, and
when at least one of the R a1 and the R a2 is a hydrogen atom, a carboxy group represented by —COOR a1 or —COOR a2 may form an acid halide or may form a salt.

6 . The polyamide resin according to claim 5 , which 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),
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 the same as defined in the formula (a1), and
when at least one of R a1 and R a2 is a hydrogen atom, and the copolymer has a carboxy group represented by —COOR a1 or —COOR a2 , the carboxy group may form an acid halide, or may form a salt.

7 . The polyamide resin according to claim 5 , wherein the weight average molecular weight is 50,000 or less.

8 . A method for producing the polyamide resin according to claim 5 , 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 , 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 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), Y 1 is a divalent organic group.

9 . A 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 formu

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Tadokoro Yoshinori
• Shiota Dai

Classifications

• G03F7/037

  the binders being polyamides or polyimides · CPC title

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• C08G73/14

  Polyamide-imides · CPC title

• C09D179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title