Photosensitive resin composition and cured product thereof

Patent metadata

Field	Value
Publication number	US-10197913-B2
Application number	US-201515516116-A
Country	US
Kind code	B2
Filing date	Sep 29, 2015
Priority date	Oct 1, 2014
Publication date	Feb 5, 2019
Grant date	Feb 5, 2019

Abstract

Provided is a photosensitive resin composition that contains (A) a photobase generator and (B) an alkali-soluble epoxy compound, wherein the photobase generator (A) contains a compound represented by formula (2-1):

and the alkali-soluble epoxy compound (B) is an epoxy compound obtained by reacting (c) a polybasic acid anhydride with a product of a reaction between (a) an epoxy compound having two or more epoxy groups in the molecule and (b) a compound having one or more hydroxyl groups and one carboxyl group in the molecule.

First claim

The invention claimed is:

1. A photosensitive resin composition comprising:
(A) a photobase generator; and
(B) an alkali-soluble epoxy compound, wherein
the photobase generator (A) comprises a compound represented by formula (2-1) below:

wherein, in formula (2-1), n represents an integer of 1 to 2;
R 1 represents at least one substituent selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an alkynyl group having 2 to 18 carbon atoms, an aryl group having 6 to 12 carbon atoms, an acyl group having 1to 18 carbon atoms, an aroyl group having 7 to 18 carbon atoms, a nitro group, a cyano group, an alkoxy group having 1 to 18 carbon atoms, an alkylthio group having 1 to 18 carbon atoms, and a halogen atom;
R 2 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkynyl group having 2 to 18 carbon atoms, an aryl group having 6 to 12 carbon atoms, an acyl group having 1 to 18 carbon atoms, an aroyl group having 7 to 18 carbon atoms, a nitro group, a cyano group, an alkoxy group having 1 to 18 carbon atoms, an alkylthio group having 1 to 18 carbon atoms, a hydroxyl group, or a halogen atom; and
X is a group represented by formula (3-1) below:

in which R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 14carbon atoms, or an arylalkyl group having 7 to 15 carbon atoms, and
the alkali-soluble epoxy compound (B) is an epoxy compound obtained by allowing (c) a polybasic acid anhydride to react with a reaction product of (a) an epoxy compound having at least two epoxy groups in one molecule and (b) a compound having at least one hydroxyl group and one carboxyl group in one molecule.

2. The photosensitive resin composition according to claim 1 , wherein the alkali-soluble epoxy compound (B) comprises an epoxy compound represented by formula (5-1):

wherein, in formula (5-1), r represents a real number of 1 or more, s represents a real number of 0 or more, provided that the sum of r and s is 30 or less, and D1 and D2 each independently represent any one of divalent bonding groups represented by formulas (6-1) to (6-10) below:

3. The photosensitive resin composition according to claim 1 , further comprising a compound having at least one urethane bond as (C) a base proliferator.

4. The photosensitive resin composition according to claim 3 , wherein the compound having at least one urethane bond is a compound having a base proliferating group represented by formula (7-1) below:

5. A cured product of the photosensitive resin composition according claim 1 .

6. A method for forming a pattern, comprising:
applying the photosensitive resin composition according to claim 1 onto a support;
drying a photosensitive resin composition layer obtained by the application;
exposing the resin composition layer to light in a predetermined pattern after the drying;
baking the resin composition layer after the exposure;
developing the resin composition layer; and
heat-treating the obtained resin pattern to obtain a cured resin pattern.

7. A photosensitive resin composition comprising:
(A) a photobase generator; and
(B) an alkali-soluble epoxy compound, wherein
the photobase generator (A) comprises a compound represented by formula (4-1) below:

wherein, R 1 represents at least one substituent selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an alkynyl group having 2 to 18 carbon atoms, an aryl group having 6 to 12 carbon atoms, an acyl group having 1 to 18 carbon atoms, an aroyl group having 7 to 18 carbon atoms, a nitro group, a cyano group, an alkoxy group having 1 to 18 carbon atoms, an alkylthio group having 1 to 18 carbon atoms, and a halogen atom,
R 2 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkynyl group having 2 to 18 carbon atoms, an aryl group having 6 to 12 carbon atoms, an acyl group having 1 to 18 carbon atoms, an aroyl group having 7 to 18 carbon atoms, a nitro group, a cyano group, an alkoxy group having 1 to 18 carbon atoms, an alkylthio group having 1 to 18 carbon atoms, a hydroxyl group, or a halogen atom,
n independently represents an integer of 0 to 4, and
p represents an integer of 1 to 6.

Assignees

• Univ Tokyo Science Found
• Nippon Kayaku Kk

Inventors

• Arimitsu Koji
• TERADA Kiwamu

Classifications

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title

• G03F7/162

  Coating on a rotating support, e.g. using a whirler or a spinner · CPC title

• G03F7/038 Primary

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title