# US 11,299,653 B2 · Composition, adhesive film, laminate, method for producing cured product pattern, and method for manufacturing circuit substrate

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- Number: US 11,299,653 B2
- Document ID: US11299653B2
- Status: Granted
- Kind: B2
- Application number: 16/598,546
- Filed: 2019-10-10
- Published: 2020-02-06
- Granted: 2022-04-12
- Earliest claimed: 2017-04-11
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Naoya Shimoju; Akinori Shibuya; Yuichiro Goto
- Web page: https://patentgrep.com/patent/US11299653B2

## CPC

- C09J 7/30: characterised by the adhesive composition
- B29C 59/026: {of layered or coated substantially flat surfaces}
- B32B 3/263: {characterised by a layer having non-uniform thickness}
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 37/12: characterised by using adhesives
- B32B 37/15: with at least one layer being manufactured and immediately laminated before reaching its stable state, e.g. in which a layer is extruded and laminated while in semi-molten state
- B32B 38/06: Embossing
- C08F 8/00: Chemical modification by after-treatment (graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C)
- C08F 220/20: of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate}
- C08F 220/283: {and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate}
- C08F 220/606: {and containing other heteroatoms}
- C08F 230/02: containing phosphorus
- C08F 290/126: {Polymers of unsaturated carboxylic acids or derivatives thereof}
- C09J 4/00: Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16}
- C09J 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
- G03F 7/0002: {Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping}
- G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence)
- B29L 2031/34: Electrical apparatus, e.g. sparking plugs or parts thereof
- B32B 2255/26: Polymeric coating
- B32B 2305/72: Cured, e.g. vulcanised, cross-linked
- B32B 2310/0831: using UV radiation
- B32B 2457/08: PCBs, i.e. printed circuit boards
- C09J 2203/326: for bonding electronic components such as wafers, chips or semiconductors
- C09J 2433/00: Presence of (meth)acrylic polymer
- H10P 76/00: Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

There are provided a composition having excellent adhesiveness and wettability, an adhesive film, a laminate, a method for producing a cured product pattern, and a method for manufacturing a circuit substrate. A composition for forming an adhesive film for imprinting, includes a compound 1 or a compound group 2; and a solvent, in which the compound 1 and the like is a compound decomposable into two or more compounds in a case where a polarity conversion group is treated, and at least one compound has a molecular weight of 30 to 400, and at least one compound has a molecular weight of 1,000 or more, the compound 1: a compound is a resin having a polymerizable group and a polarity conversion group, in which the resin has the polarity conversion group in at least a main chain or a side chain, the polarity conversion group is bonded to the main chain of the resin via a linking group in a case where the polarity conversion group is provided in the side chain, and the number of atoms constituting a chain of the linking group is 8 or more; and the compound group 2: a compound that has a polymerizable group and does not have a polarity conversion group, and a compound that does not have a polymerizable group and has a polarity conversion group.

## Claims

### Claim 1

A composition for forming an adhesive film for imprinting, comprising:
at least one of the following compound 1 and the following compound group 2,
the compound 1: a compound that has a polymerizable group and a polarity conversion group, and is a resin, in which the resin has the polarity conversion group in at least a main chain or a side chain, the polarity conversion group is bonded to the main chain of the resin via a linking group in a case where the polarity conversion group is provided in the side chain, and the number of atoms constituting a chain of the linking group is 8 or more, and
the compound group 2: a compound that has a polymerizable group and does not have a polarity conversion group, and a compound that does not have a polymerizable group and has a polarity conversion group; and
a solvent,
wherein a content of the solvent in the composition is 80 mass % or more,
the compound having a polymerizable group and a polarity conversion group, and the compound not having a polymerizable group and having a polarity conversion group each independently are a compound decomposable into two or more compounds in a case where the polarity conversion group is treated, and
among the two or more compounds, at least one compound has a molecular weight of 30 to 400, and at least one compound has a molecular weight of 1,000 or more.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein the treatment is at least one of heating at 100° C. to 250° C., light irradiation, and chemical treatment.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein the compound having a molecular weight of 30 to 400 among the generated compounds is selected from alkene, ether, aldehyde, alcohol, carbon dioxide, sulfonic acid, and carboxylic acid.

### Claim 4 (depends on 1)

The composition according to claim 1, comprising at least the compound 1.

### Claim 5 (depends on 4)

The composition according to claim 4, comprising the compound that does not have a polymerizable group and has a polarity conversion group.

### Claim 6 (depends on 1)

The composition according to claim 1, wherein the compound 1 is a (meth)acrylic resin.

### Claim 7 (depends on 1)

The composition according to claim 1,
wherein at least one of repeating units having a polarity conversion group constituting the resin that is the compound 1 is a repeating unit derived from a monomer having the polarity conversion group, and
a C log P value of the monomer corresponding to a repeating unit obtained after subjecting the repeating unit having the polarity conversion group to the treatment is −10 to 0, provided that the C log P value is a coefficient showing affinity of an organic compound with respect to water and 1-octanol.

### Claim 8 (depends on 1)

The composition according to claim 1, wherein the compound 1 further has an alkyleneoxy chain.

### Claim 9 (depends on 1)

The composition according to claim 1, wherein a critical surface tension of a film formed of the component excluding the solvent from the composition is 35 mN/m or less, and a critical surface tension after the treatment of a film formed of the component excluding the solvent from the composition is 42 mN/m or more.

### Claim 10 (depends on 1)

An adhesive film formed from the composition according to claim 1.

### Claim 11 (depends on 10)

The adhesive film according to claim 10, wherein a critical surface tension is 42 mN/m or more.

### Claim 12 (depends on 10)

A laminate comprising:
a substrate; and
an adhesive film positioned on a surface of the substrate,
wherein the adhesive film is the adhesive film according to claim 10.

### Claim 13 (depends on 12)

The laminate according to claim 12, further comprising a layer formed from a curable composition for imprinting on a surface of the adhesive film.

### Claim 14 (depends on 12)

The laminate according to claim 12, further comprising a cured product pattern formed of a curable composition for imprinting on a surface of the adhesive film.

### Claim 15 (depends on 1)

A method for producing a cured product pattern, the method comprising:
an adhesive film formation step of forming an adhesive film by applying the composition according to claim 1 onto a substrate;
an application step of applying a curable composition for imprinting onto a surface of the adhesive film;
a mold contact step of bringing the curable composition for imprinting into contact with a mold having a pattern for transferring a pattern shape;
a light irradiation step of irradiating the curable composition for imprinting with light to form a cured product; and
a release step of separating the cured product and the mold from each other.

### Claim 16 (depends on 15)

A method for manufacturing a circuit substrate, the method comprising:
a step of obtaining a cured product pattern through the production method according to claim 15.