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JP-7855983-B2 - Photosensitive resin composition, method for manufacturing a resist pattern film, and method for manufacturing a plated object

JP7855983B2JP 7855983 B2JP7855983 B2JP 7855983B2JP-7855983-B2

Inventors

  • 佐藤 慶一
  • 石井 亮
  • 富田 卓弥
  • 香村 和彦

Assignees

  • ＪＳＲ株式会社

Dates

Publication Date
20260511
Application Date
20220927

Claims (11)

  1. (A) Alkali-soluble resin, (B1) A polymerizable compound having at least two (meth)acryloyl groups and two hydroxyl groups in one molecule, and having an alicyclic hydrocarbon structure. (C) Photoradical polymerization initiator, (D) At least one compound selected from the group consisting of nitrogen-containing heterocyclic compounds (d1) containing two or more nitrogen atoms and thiol compounds (d2), and (F) a solvent, The polymerizable compound (B1) is (i) a reaction product of epoxy (meth)acrylate and alicyclic dicarboxylic acids, and (ii) a reaction product of alicyclic dicarboxylic acid diglycidyl ester and (meth)acrylic acid, The nitrogen-containing heterocyclic compound (d1) is at least one selected from the group consisting of imidazoles, triazoles, and purine derivatives. A photosensitive resin composition wherein the photoradical polymerization initiator (C) comprises an oxime-based photoradical polymerization initiator (C1) and a non-oxime-based photoradical polymerization initiator (C2).
  2. The photosensitive resin composition according to claim 1, wherein the polymerizable compound (B1) has at least two structures represented by the following formula (1) in one molecule. [In formula (1), R1 represents a hydrogen atom or a methyl group. * represents a bond.]
  3. The photosensitive resin composition according to claim 1, further containing a polymerizable compound (B2) other than the polymerizable compound (B1).
  4. The photosensitive resin composition according to claim 1, wherein the compound (D) comprises the nitrogen-containing heterocyclic compound (d1).
  5. The photosensitive resin composition according to claim 1, comprising 0.05 to 20 parts by mass of compound (D) per 100 parts by mass of polymerizable compound (B1).
  6. The photosensitive resin composition according to claim 1, wherein the alkali-soluble resin (A) has a phenolic hydroxyl group-containing structural unit represented by the following formula (2). [In formula (2), R 2 represents a hydrogen atom or a methyl group.]
  7. The photosensitive resin composition according to claim 6 , wherein the content of the phenolic hydroxyl group-containing structural unit in 100% by mass of the alkali-soluble resin (A) is in the range of 1 to 40% by mass.
  8. A method for manufacturing a resist pattern film, comprising the steps of: (1) applying a photosensitive resin composition according to any one of claims 1 to 7 onto a substrate to form a resin coating film; (2) exposing the resin coating film to light; and (3) developing the resin coating film after exposure.
  9. A method for producing a resist pattern film according to claim 8 , wherein a resist pattern film is formed on a copper film.
  10. The method for manufacturing a resist pattern film according to claim 8 , wherein the thickness of the resin coating film formed in step (1) is 250 μm or more.
  11. A method for manufacturing a plated object, comprising the step of performing a plating treatment on the substrate using a resist pattern film manufactured by the manufacturing method described in claim 8 as a mask.

Description

This invention relates to a photosensitive resin composition, a method for manufacturing a resist pattern film, and a method for manufacturing plated molded objects. In recent years, semiconductor elements and connection elements such as bumps on display elements like liquid crystal displays and touch panels require high-precision placement on substrates. Generally, bumps and similar objects are plated molded products. As described in Patent Document 1, they are manufactured by forming a thick resist pattern on a substrate having a metal foil such as copper, using the thick resist pattern as a mask (template), and then performing plating. Among thick-film resist patterns, there is a growing demand for resist patterns with a film thickness range (≥250 μm) that requires three coats of the photosensitive resin composition onto the substrate. Japanese Patent Publication No. 2006-285035 [Photosensitive resin composition] The photosensitive resin composition of the present invention is a resin composition for forming a resist pattern film. The photosensitive resin composition contains an alkali-soluble resin (A), a polymerizable compound (B1) having at least two (meth)acryloyl groups and hydroxyl groups in one molecule and having a ring structure, a photoradical polymerization initiator (C), at least one compound (D) selected from the group consisting of nitrogen-containing heterocyclic compounds (d1) containing two or more nitrogen atoms, thiol compounds (d2), and polymerization inhibitors (d3), and a solvent (F). It may further contain a polymerizable compound other than compound (B1) (B2), a surfactant, etc., as needed. <Alkali-soluble resin (A)> The alkali-soluble resin (A) is a resin that has the property of dissolving in an alkaline developer to a degree that allows for the desired developing treatment. Examples of alkali-soluble resins include those described in Japanese Patent Publication No. 2008-276194, Japanese Patent Publication No. 2003-241372, Japanese Patent Publication No. 2009-531730, WO2010/001691, Japanese Patent Publication No. 2011-123225, Japanese Patent Publication No. 2009-222923, and Japanese Patent Publication No. 2006-243161. The weight-average molecular weight (Mw) of the alkali-soluble resin (A) in terms of polystyrene, as measured by gel permeation chromatography, is preferably in the range of 1,000 to 1,000,000, more preferably 2,000 to 50,000, and particularly preferably 3,000 to 20,000. Furthermore, the alkali-soluble resin (A) is preferably one having phenolic hydroxyl groups, as this improves the developability and pattern shape of the resist pattern film. As the alkali-soluble resin (A) having phenolic hydroxyl groups, an alkali-soluble resin (A1) having a structural unit represented by the following formula (2) (hereinafter also referred to as "structural unit (2)") is preferred. [In formula (2), R 2 represents a hydrogen atom or a methyl group.] By using an alkali-soluble resin (A1) having structural unit (2), a resist pattern that is less prone to swelling during the plating process can be obtained. As a result, lifting or peeling of the resist pattern from the substrate is prevented, thus preventing the plating solution from seeping into the interface between the substrate and the resist pattern, even when the plating process is performed for a long time. Furthermore, improved resolution can also be achieved. The content of structural unit (2) in the alkali-soluble resin (A1) having structural unit (2) is preferably in the range of 1 to 40% by mass, more preferably in the range of 5 to 30% by mass. By having a structural unit (2) content within this range, that is, by using monomers that lead to structural unit (2) in such amounts, the molecular weight of the alkali-soluble resin (A1) can be sufficiently increased. Furthermore, a resist pattern that is less prone to swelling during the plating process can be obtained. ≪Monomer (2')≫ Alkali-soluble resins (A1) having structural unit (2) can be obtained by polymerization using, for example, hydroxyl group-containing aromatic vinyl compounds such as o-hydroxystyrene, m-hydroxystyrene, p-hydroxystyrene, and p-isopropenylphenol (hereinafter also referred to as "monomer (2')") as part of the raw material monomer. These monomers (2') may be used individually or in combination of two or more. Among these monomers (2'), p-hydroxystyrene and p-isopropenylphenol are preferred, and p-hydroxystyrene is more preferred, in that they yield a resin composition capable of forming a resist pattern with excellent long-term plating resistance. <<Monomer (I)>> The alkali-soluble resin (A1) having structural unit (2) may further have structural units derived from other monomers copolymerizable with monomer (2') (hereinafter also referred to as "monomer (I)"). Examples of monomers (I) include aromatic vinyl compounds such as styrene, α-methylstyrene, p-methylstyrene, and p-methoxystyrene; Heteroatom-containing alicyclic vinyl compounds such as N-v