# US 10,246,605 B2 · Resin composition for underlayer film formation, layered product, method for forming pattern, imprint forming kit, and process for producing device

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- Number: US 10,246,605 B2
- Document ID: US10246605B2
- Status: Granted
- Kind: B2
- Application number: 15/441,716
- Filed: 2017-02-24
- Published: 2017-06-08
- Granted: 2019-04-02
- Earliest claimed: 2014-08-27
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Tadashi Oomatsu; Hirotaka Kitagawa; Yuichiro Goto
- Web page: https://patentgrep.com/patent/US10246605B2

## CPC

- C08F 222/10: Esters
- B29C 59/005: {characterised by the choice of material}
- B29C 59/16: by wave energy or particle radiation {, e.g. infrared heating (B29C59/007 takes precedence)}
- B32B 27/00: Layered products comprising {a layer of} synthetic resin {(fibrous or filamentary layer made of a synthetic resin B32B5/02; particulate layer made of a synthetic resin B32B5/16; foamed layer made of a synthetic resin B32B5/18)}
- C08F 220/20: of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate}
- C08F 265/02: on to polymers of acids, salts or anhydrides
- C08F 290/142: {Polyethers}
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 5/32: Radiation-absorbing paints {(protection against X-, gamma- or corpuscular radiation G21F)}
- C09D 7/40: Additives
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D 135/02: Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence)
- C09D 151/003: {grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds (C09D151/04, C09D151/06 take precedence)}
- C09D 151/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C09D 201/02: characterised by the presence of specified groups {, e.g. terminal or pendant functional groups}
- G03F 7/0002: {Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping}
- G03F 7/0752: {in non photosensitive layers or as additives, e.g. for dry lithography}
- G03F 7/094: {Multilayer resist systems, e.g. planarising layers}
- H10P 14/6342: {Liquid deposition, e.g. spin-coating, sol-gel techniques or spray coating}
- H10P 14/6536: {by exposure to radiation, e.g. visible light}
- H10P 14/683: {carbon-based polymeric organic materials, e.g. polyimides, poly cyclobutene or PVC}
- H10P 95/08: {Planarisation of organic insulating materials}
- B29C 59/02: by mechanical means, e.g. pressing {(B29C59/007 takes precedence; embossing expanded porous articles B29C44/5627)}
- B29K 2033/08: {Polymers of acrylic acid esters, e.g. PMA, i.e. polymethylacrylate}
- C08F 2438/02: Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO]
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- 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)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS

## Abstract

Provided are a resin composition for underlayer film formation with which a variation hardly occurs in the line width distribution after processing due to a small thickness of a residual film after mold pressing, a layered product, a method for forming a pattern, an imprint forming kit, and a process for producing a device. Disclosed is a resin composition for underlayer film formation which is used to form an underlayer film by being applied onto a base material, including a first resin having a radical reactive group in the side chain, a second resin containing at least one selected from a fluorine atom and a silicon atom, and a solvent. The second resin is preferably a resin containing a fluorine atom. The radical reactive group of the first resin is preferably a (meth)acryloyl group.

## Claims

### Claim 1

A resin composition for underlayer film formation which is used to form an underlayer film by being applied onto a base material, comprising:
a first resin having a radical reactive group in a side chain;
a second resin containing at least one selected from a fluorine atom and a silicon atom; and
a solvent,
wherein the second resin contains a repeating unit having a fluorine atom and a repeating unit represented by General Formula (CIII):
wherein Rc31 represents a hydrogen atom, an alkyl group, a cyano group, or a CH2—O-Rac2 group; Rac2 represents a hydrogen atom, an alkyl group, or an acyl group; Rc32 represents a group having an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, or an aryl group; and Lc3 represents a single bond or a divalent linking group; and
the repeating unit having a fluorine atom contains at least one unit selected from the group consisting Formulae (C-Ia) to (C-Id):
wherein R10 and R11 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group; and W3 to W6 each independently represents an organic group containing at least one or more fluorine atoms.

### Claim 2 (depends on 1)

The resin composition for underlayer film formation according to claim 1, wherein 0.01 to 20 mass % of the second resin is contained with respect to the total solids content of the resin composition for underlayer film formation.

### Claim 3 (depends on 1)

The resin composition for underlayer film formation according to claim 1, wherein the radical reactive group contained in the first resin is a (meth)acryloyl group.

### Claim 4 (depends on 1)

The resin composition for underlayer film formation according to claim 1, wherein the first resin has a radical reactive group, and at least one group selected from a group represented by General Formula (B), an oxiranyl group, an oxetanyl group, a nonionic hydrophilic group, and a group having an interaction with a base material in a side chain:
in General Formula (B), a wavy line represents a position of connection to a main chain or side chain of the resin,
Rb1, Rb2, and Rb3 each independently represent a group selected from an unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms and an unsubstituted cycloalkyl group having 3 to 20 carbon atoms, and
two of Rb1, Rb2, and Rb3 may be bonded to each other to form a ring.

### Claim 5 (depends on 1)

The resin composition for underlayer film formation according to claim 1, wherein the first resin has at least one repeating unit selected from the following (X1) to (X4):
in Formulae (X1) to (X4), RX1, RX2, and RX3 each independently represent a hydrogen atom or a methyl group, and a wavy line represents a position of connection to a side chain of the resin.

### Claim 6 (depends on 1)

The resin composition for underlayer film formation according to claim 1, wherein the resin composition for underlayer film formation contains a solvent in the range of 95 to 99.9 mass %.

### Claim 7 (depends on 1)

The resin composition for underlayer film formation according to claim 1, wherein a contact angle of the film formed of the resin composition for underlayer film formation with respect to water is 50° or more, and a contact angle of the film with respect to diiodomethane is 30° or more.

### Claim 8 (depends on 1)

The resin composition for underlayer film formation according to claim 1, which is used in the formation of an underlayer film for imprints.

### Claim 9 (depends on 1)

A layered product comprising an underlayer film obtained by curing the resin composition for underlayer film formation according to claim 1, on a surface of a base material.

### Claim 10 (depends on 1)

A method for forming a pattern, comprising:
applying the resin composition for underlayer film formation according to claim 1 onto a surface of a base material in the form of a layer;
heating the applied resin composition for underlayer film formation to form an underlayer film;
applying a photocurable composition onto a surface of the underlayer film in the form of a layer;
pressing a mold having a pattern on the photocurable composition;
curing the photocurable composition by photoirradiation in a state of the mold being pressed; and
separating the mold.

### Claim 11 (depends on 1)

An imprint forming kit comprising:
the resin composition for underlayer film formation according to claim 1; and
a photocurable composition.

### Claim 12 (depends on 11)

The imprint forming kit according to claim 11, wherein a contact angle of the film formed of the resin composition for underlayer film formation with respect to a photocurable composition is 10° or more.

### Claim 13 (depends on 10)

A process for producing a device, comprising the method for forming a pattern according to claim 10.

### Claim 14 (depends on 1)

The resin composition for underlayer film formation according to claim 1, wherein the content of the second resin is 10 to 20 mass % with respect to the total solids content of the resin composition for underlayer film formation.

### Claim 15 (depends on 1)

The resin composition for underlayer film formation according to claim 1, wherein the repeating unit having a fluorine atom contains at least one unit of Formulae (C-Ia).