Chemically amplified positive-type photosensitive resin composition, method for manufacturing substrate with template, and method for manufacturing plated article

Patent metadata

Field	Value
Publication number	US-11402755-B2
Application number	US-201916294254-A
Country	US
Kind code	B2
Filing date	Mar 6, 2019
Priority date	Mar 12, 2018
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

A chemically amplified positive-type photosensitive resin composition capable of forming a resist pattern having excellent cross-sectional perpendicularity of a nonresist section even when a resist pattern is formed on a metal surface, and a method for manufacturing a substrate with a template and a method for manufacturing a plated article using the composition. The composition contains an acid generator, a resin, and a sulfur-containing compound including a sulfur-containing compound and a thiol compound that is different from the sulfur-containing compound.

First claim

What is claimed is:

1. A chemically amplified positive-type photosensitive resin composition comprising:
an acid generator (A) that produces an acid by irradiation with an active ray or radiation;
a resin (B) whose solubility in alkali increases under an action of acid;
and a sulfur-containing compound (C), wherein the sulfur-containing compound (C) comprises a sulfur-containing compound (C1), and a thiol compound (C2) that is different from the sulfur-containing compound (C1), and
wherein the sulfur-containing compound (C1) is a compound represented by at least one of the following formulae (c1-1) and (c1-2):

wherein in the formulae (c1-1) and (c1-2), a ring A is a monocyclic ring having 4 or more and 8 or less ring-forming atoms, or a polycyclic ring having 5 or more and 20 or less ring-forming atoms, X is —CR 1c R 2c —, —NR 3c —, —O—, —S—, —Se—, —Te—, ═CR 4c —, or ═N—, and R 1c , R 2c , R 3c , and R 4c each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, or an organic group,
wherein the compound represented by the formula (c1-1) has one mercapto group in a molecule, and does not have a hydroxyl group; and the compound represented by the formula (c1-2) does not have a mercapto group and a hydroxyl group in the molecule,
the composition comprises more than 0.05 and 2 parts by mass or less of the sulfur-containing compound (C) relative to 100 parts by mass of the resin (B), and
the composition comprises 0.05 parts by mass or more and less than 2 parts by mass of the thiol compound (C2) relative to 100 parts by mass of the resin (B).

2. The chemically amplified positive-type photosensitive resin composition according to claim 1 , wherein a number of the ring-forming atoms in the ring A is 5 or more and 7 or less, and the ring A includes 1 or more and 3 or less nitrogen atoms as the ring-forming atoms.

3. The chemically amplified positive-type photosensitive resin composition according to claim 1 , further comprising an alkali soluble resin (D).

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

5. A method for manufacturing a substrate with a template, the method comprising:
forming a photosensitive resin layer on a metal surface of a substrate having the metal surface, the photosensitive resin layer comprising the chemically amplified positive-type photosensitive resin composition according to claim 1 ;
irradiating the photosensitive resin layer with an active ray or radiation to perform exposure; and
developing the photosensitive resin layer after the exposure to create a template for forming a plated article.

6. A method for manufacturing a plated article, the method comprising plating the substrate with a template manufactured by the method according to claim 5 to form the plated article within the template.

7. The chemically amplified positive-type photosensitive resin composition according to claim 1 , wherein the thiol compound (C2) comprises at least one selected from the group consisting of a compound represented by the following formula (c2-2) and a benzene-polythiol compound:

wherein R c5 and R c6 each independently represents a hydrogen atom or an alkyl group, R c7 represents a single bond or an alkylene group, R c8 represents an aliphatic group having a valence of u, which may include an atom other than a carbon atom, and u is an integer of 2 or more and 4 or less,
wherein the thiol compound (C2) does not include any tautomer of the sulfur-containing compound (C1), and
wherein the benzene-polythiol compound comprises at least one selected from the group consisting of 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,2-bis(mercaptoethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris(mercaptomethyl)benzene, 1,2,4-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptomethyl)benzene, 1,2,3-tris(mercaptoethyl)benzene, 1,2,4-tris(mercaptoethyl)benzene, 1,3,5-tris(mercaptoethyl)benzene, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,3-di(p-methoxyphenyl)propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-di(p-mercaptophenyl)pentane, 1,2-bis(mercaptoethylthio)benzene, 1,3-bis(mercaptoethylthio)benzene, 1,4-bis(mercaptoethylthio)benzene, 1,2,3-tris(mercaptomethylthio)benzene, 1,2,4-tris(mercaptomethylthio)benzene, 1,3,5-tris(mercaptomethylthio)benzene, 1,2,3-tris(mercaptoethylthio)benzene, 1,2,4-tris(mercaptoethylthio)benzene, and 1,3,5-tris(mercaptoethylthio)benzene.

Assignees

• Tokyo Ohka Kogyo Co Ltd
• Tokyo Inst Tech

Inventors

• Kuroiwa Yasushi
• Yamamoto Yuta

Classifications

• C08K5/36

  Sulfur-, selenium-, or tellurium-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• C08L25/18

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title

• C08L61/06

  of aldehydes with phenols · CPC title

• G03F7/30

  Imagewise removal using liquid means · CPC title