Chemically amplified positive-type photosensitive resin composition

Patent metadata

Field	Value
Publication number	US-10054855-B2
Application number	US-201615074124-A
Country	US
Kind code	B2
Filing date	Mar 18, 2016
Priority date	Mar 31, 2015
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

A photosensitive resin composition, a method of manufacturing a substrate with a template using the composition, and a method of manufacturing a plated article using the substrate with a template. The photosensitive resin composition may be used to form a plated article on a metal surface of a substrate The composition includes an acid generator that, when irradiated with an active ray or radiation, generates an acid, a resin that, under an action of an acid, undergoes an increase in solubility thereof in alkali, and a fluorene compound represented by the formula (1).

First claim

What is claimed is:

1. A photosensitive resin composition comprising: an (A) acid generator; a (B) resin; and a fluorene compound, wherein
the (A) acid generator, when irradiated with an active ray or radiation, generates an acid,
the (B) resin, under action of an acid, undergoes an increase in solubility in alkali, wherein
the fluorene compound in the photosensitive resin composition consists essentially of (C) a fluorene compound is represented by the formula (1):

wherein each of ring Z 1 and ring Z 2 independently represents a benzene ring or a naphthalene ring; each of X 1 and X 2 independently represents a single bond or —S—; each of R 1 and R 2 independently represents a hydroxyl group or a (meth)acryloyloxy group; each of R 3 and R 4 independently represents a monovalent hydrocarbon group, a hydroxyl group, a (meth)acryloyloxy group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxy group, an amino group, a carbamoyl group, a group represented by —NHR 4c , a group represented by —N(R 4d ) 2 , a sulfo group, or a group in which at least a part of the hydrogen atoms bonded to a carbon atom contained in a monovalent hydrocarbon group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a group represented by —NHR 4c , or a group represented by —N(R 4d ) 2 is substituted by a monovalent hydrocarbon group, a hydroxyl group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxy group, an amino group, a carbamoyl group, a group represented by —NHR 4c , a group represented by —N(R 4d ) 2 , a (meth)acryloyloxy group, a mesyloxy group, or a sulfo group; each of R 4a to R 4d independently represents a monovalent hydrocarbon group; k1 and k2 represent 1; and
each of k3 and k4 independently represents an integer of 0 to 4.

2. The photosensitive resin composition according to claim 1 , further comprising an (D) alkali soluble resin.

3. The photosensitive resin composition according to claim 2 , wherein the (D) alkali soluble resin comprises at least one selected from the group consisting of a (D1) novolak resin, a (D2) polyhydroxystyrene resin and an (D3) acrylic resin.

4. The photosensitive resin composition according to claim 1 , wherein each of the ring Z 1 and ring Z 2 represents a benzene ring.

5. The photosensitive resin composition according to claim 1 , further comprising an (S) organic solvent.

6. A method of manufacturing a substrate with a template, the method comprising:
forming a photosensitive resin layer by coating the photosensitive resin composition according to claim 1 in liquid form on a metal surface of a substrate and removing a solvent;
irradiating the layer with an active ray or radiation; and
developing the exposed layer to form a template for forming a plated article.

7. The method according to claim 6 , wherein the photosensitive resin composition further comprises an (D) alkaline soluble resin.

8. The method according to claim 7 , wherein the (D) alkaline soluble resin comprises at least one selected from the group consisting of a (D1) novolak resin, a (D2) polyhydroxystyrene resin and an (D3) acrylic resin.

9. The method according to claim 6 , wherein each of the ring Z 1 and ring Z 2 represents a benzene ring in the (C) fluorene compound included in the photosensitive resin composition.

10. A method of manufacturing a plated article, the method comprising:
plating non-resist sections on the substrate with the template manufactured by the method according to claim 6 to form the plated article within the template, and removing the remaining template to form the article.

11. The method according to claim 10 , wherein the photosensitive resin composition further comprises an (D) alkaline soluble resin.

12. The method according to claim 11 , wherein the (D) alkaline soluble resin comprises at least one selected from the group consisting of a (D1) novolak resin, a (D2) polyhydroxystyrene resin and an (D3) acrylic resin.

13. The method according to claim 10 , wherein each of the ring Z 1 and ring Z 2 represents a benzene ring in the (C) fluorene compound included in the photosensitive resin composition.

14. A photosensitive resin composition comprising; an (A) acid generator, a (B) resin, and a fluorene compound, wherein
the (A) acid generator, when irradiated with an active ray or radiation, generates an acid, the (B) resin, under action of an acid, undergoes an increase in solubility in alkali, wherein
the flurorene compound in the photosensitive resin composition consists of a (C) fluorene compound represented by formula (1) below:

wherein each of ring Z 1 and Z 2 independently represents a benzene ring or a naphthalene ring; each of X 1 and X 2 independently represents a single bond or S; each of R 1 and R 2 independently represents a hydroxyl group or a (meth)acryloyloxy group; each of R 3 and R 4 independently represents a monovalent hydrocarbon group, a hydroxyl group, a (meth)acryloyloxy group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR 4c , a group represented by —N(R 4d ) 2 , a (meth)acryloyloxy group, a sulfo group, or a group in which at least a part of the hydrogen atoms bonded to a carbon atom contained in a monovalent hydrocarbon group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a group represented by —NHR 4c or a group represented by —N(R 4d ) 2 , is substituted by a monovalent hydrocarbon group, a hydroxyl group, a group represented by —OR 4a , a group represented by —SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR 4c , a group represented by —N(R 4d ) 2 , a (meth)acryloyloxy group, a mesyloxy group, or a sulfo group; each of R 4a to R 4d independently represents a monovalent hydrocarbon group; k1 and k2 represent 1; and each of k3 and k4 independently represents an integer of 0 to 4.

15. The photosensitive resin composition according to claim 14 , wherein each of the ring Z 1 and ring Z 2 represents a benzene ring.

16. The photosensitive resin composition according to claim 14 , further comprising an (S) organic solvent.

17. The photosensitive resin composition according to claim 14 , wherein the photosensitive resin composition further comprises an (D) alkaline soluble resin.

18. The photosensitive resin composition according to claim 17 , wherein the (D) alkaline soluble resin comprises at least one selected from the group consisting of a (D1) novolak resin, a (D2) polyhydroxystyrene resin and an (D3) acrylic resin.

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Katayama Shota
• Momozawa Aya

Classifications

• H10P76/4085

  characterised by the processes involved to create the masks · CPC title

• H10P76/2041

  Photolithographic processes · CPC title

• H10P50/283

  by chemical means · CPC title

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title