IP Library Granted Patent US 10,564,543
Granted Patent B2
US 10,564,543 · App. 15/510,211 · Granted Feb 18, 2020

Photosensitive resin composition, photosensitive element, method for producing substrate with resist pattern, and method for producing printed wiring board

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Quick Facts
Patent No.
US 10,564,543
App. No.
15/510,211
Granted
Feb 18, 2020
Kind
B2
Abstract

A photosensitive resin composition includes (A) a binder polymer having a structural unit derived from a hydroxyalkyl (meth)acrylate ester having a hydroxyalkyl group having from 1 to 12 carbon atoms, and a structural unit derived from a (meth)acrylic acid; (B) a photopolymerizable compound having an ethylenically unsaturated bond group; (C) a photopolymerization initiator; and (D) a styryl pyridine represented by the Formula (1). In Formula (1), each of R 1 , R 2 and R 3 independently represents an alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, an alkyl ester group having from 1 to 6 carbon atoms, an amino group, an alkyl amino group having from 1 to 20 carbon atoms, a carboxy group, a ciano group, a nitro group, an acetyl group or a (meth)acryloyl group, each of a, b and c independently represents an integer of from 0 to 5. In a case in which each of a, b and c is independently 2 or more, the plural R 1 s, R 2 s, and R 3 s independently may be the same or different.

Claims (42)

1. A photosensitive resin composition, comprising:

(A) a binder polymer having a structural unit derived from a hydroxyalkyl (meth)acrylate ester having a hydroxyalkyl group having from 1 to 12 carbon atoms, and a structural unit derived from a (meth)acrylic acid, the binder polymer having a weight-average molecular weight (Mw) ranging from 10,000 to 15,000;

(B) a photopolymerizable compound having an unsaturated bond group, the (B) photopolymerizable compound comprising a structure represented by the following Formula (3):

wherein, in Formula (3), each of R 4 and R 5 independently represents a hydrogen atom or a methyl group, each of m 1 , m 2 , n 1 and n 2 independently represents an integer of 0 or more, the total of m 1 +m 2 +n 1 +n 2 is greater than 0, each of XO and YO independently represents an ethyleneoxy group or a propyleneoxy group, and the photopolymerizable compound includes at least one selected from a propyleneoxy group or a polypropyleneoxy group;

(C) a photopolymerization initiator; and

(D) a styryl pyridine represented by the Formula (1);

wherein, in Formula (1), each of R 1 , R 2 and R 3 independently represents an alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, an alkyl ester group having from 1 to 6 carbon atoms, an amino group, an alkyl amino group having from 1 to 20 carbon atoms, a carboxy group, a ciano group, a nitro group, an acetyl group or a (meth)acryloyl group, each of a, b and c independently represents an integer of from 0 to 5, with the proviso that when a is 2 or more, the plural R 1 s are the same or different, when b is 2 or more, the plural R 2 s are the same or different, and when c is 2 or more, the plural R 3 s are the same or different.

2. The photosensitive resin composition according to claim 1 , wherein (A) the binder polymer further has a structural unit derived from styrene or α-methylstyrene.

3. The photosensitive resin composition according to claim 1 , wherein (C) the photopolymerization initiator includes at least one selected from the group consisting of 2,4,5-triarylimidazole dimer and a derivative thereof.

4. A photosensitive element, comprising:

a support; and

a photosensitive resin composition layer that is provided on the support and that is formed from the photosensitive resin composition according to claim 1 .

5. A method for producing a substrate with a resist pattern, the method comprising:

forming a photosensitive resin composition layer on a substrate using the photosensitive resin composition according to claim 1 ;

irradiating at least a part of an area of the photosensitive resin composition layer with active light rays, and photo-curing the area to form a cured material area; and

removing an area other than the cured material area of the photosensitive resin composition layer from the substrate to form a resist pattern, which is the cured material area, on the substrate.

6. The method for producing a substrate with a resist pattern according to claim 5 , wherein the active light rays have a wavelength in a range of from 340 nm to 430 nm.

7. A method for producing a printed wiring board, the method comprising:

subjecting the substrate with the resist pattern which has been formed using the method for producing a substrate with a resist pattern according to claim 5 , to at least one of etching or plating.

8. The photosensitive resin composition according to claim 1 , wherein each of m 1 , m 2 , n 1 and n 2 independently represents an integer of 0 to 40.

9. A multilayer substrate comprising:

a copper-clad laminate comprising:

a glass epoxy material, and

copper foil formed on both sides of the glass epoxy material; and

a photosensitive element comprising:

a support, and

a photosensitive resin composition layer provided on the support, the photosensitive resin composition layer contacting the copper foil on a side of the copper-clad laminate, the photosensitive resin composition layer including a photosensitive resin composition comprising:

(A) a binder polymer having a structural unit derived from a hydroxyalkyl (meth)acrylate ester having a hydroxyalkyl group having from 1 to 12 carbon atoms, and a structural unit derived from a (meth)acrylic acid, the binder polymer having a weight-average molecular weight (Mw) ranging from 10,000 to 15,000;

(B) a photopolymerizable compound having an unsaturated bond group, the (B) photopolymerizable compound comprising a structure represented by the following Formula (3):

wherein, in Formula (3), each of R 4 and R 5 independently represents a hydrogen atom or a methyl group, each of m 1 , m 2 , n 1 and n 2 independently represents an integer of 0 or more, the total of m 1 +m 2 +n 1 +n 2 is greater than 0, each of XO and YO independently represents an ethyleneoxy group or a propyleneoxy group, and the photopolymerizable compound includes at least one selected from a propyleneoxy group or a polypropyleneoxy group;

(C) a photopolymerization initiator; and

(D) a styryl pyridine represented by the Formula (1);

wherein, in Formula (1), each of R 1 , R 2 and R 3 independently represents an alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, an alkyl ester group having from 1 to 6 carbon atoms, an amino group, an alkyl amino group having from 1 to 20 carbon atoms, a carboxy group, a ciano group, a nitro group, an acetyl group or a (meth)acryloyl group, each of a, b and c independently represents an integer of from 0 to 5, with the proviso that when a is 2 or more, the plural R's are the same or different, when b is 2 or more, the plural R 2 s are the same or different, and when c is 2 or more, the plural R 3 s are the same or different.

10. The multilayer substrate according to claim 9 , wherein (A) the binder polymer further has a structural unit derived from styrene or α-methylstyrene.

11. The multilayer substrate according to claim 9 , wherein (C) the photopolymerization initiator includes at least one selected from the group consisting of 2,4,5-triarylimidazole dimer and a derivative thereof.

12. The multilayer substrate according to claim 9 , wherein each of m 1 , m 2 , n 1 and n 2 independently represents an integer of 0 to 40.

13. A method for producing a multilayer substrate with a resist pattern, the method comprising:

irradiating at least a part of an area of the photosensitive resin composition layer of the multilayer substrate of claim 9 with active light rays, and photo-curing the area to form a cured material area; and

removing an area other than the cured material area of the photosensitive resin composition layer from the multilayer substrate to form a resist pattern, which is the cured material area, on the multilayer substrate.

14. The method for producing a multilayer substrate with a resist pattern according to claim 13 , wherein the active light rays have a wavelength in a range of from 340 nm to 430 nm.

15. A method for producing a printed wiring board, the method comprising:

subjecting the multilayer substrate with the resist pattern which has been formed using the method for producing a multilayer substrate with a resist pattern according to claim 13 , to at least one of etching or plating.

Assignments (4)
CHANGE OF ADDRESS Recorded Feb 14, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066599/0037 →
CHANGE OF NAME Recorded Mar 3, 2023
From: SHOWA DENKO MATERIALS CO., LTD.
To: RESONAC CORPORATION
Reel/Frame 062946/0125 →
CHANGE OF NAME Recorded Mar 2, 2023
From: HITACHI CHEMICAL COMPANY, LTD.
To: SHOWA DENKO MATERIALS CO., LTD.
Reel/Frame 062917/0865 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 10, 2017
From: OKADE, SHOTA; MURAMATSU, YUKIKO; OOTA, EMIKO; SAWABE, KEN; RI, SANCHORU
To: HITACHI CHEMICAL COMPANY, LTD.
Reel/Frame 041537/0395 →