# US 2019/0171104 A1 · Actinic ray-sensitive or radiation-sensitive resin composition, actinic ray-sensitive or radiation-sensitive film, pattern forming method, method of manufacturing electronic device, compound, and resin

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- Number: US 2019/0171104 A1
- Document ID: US20190171104A1
- Status: Published application
- Kind: A1
- Application number: 16/266,719
- Filed: 2019-02-04
- Published: 2019-06-06
- Earliest claimed: 2016-08-26
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Akira Takada; Ryo Nishio; Akiyoshi Goto; Michihiro Shirakawa; Naohiro Tango; Kazuhiro Marumo; Kyohei Sakita
- Web page: https://patentgrep.com/patent/US20190171104A1

## CPC

- C08F 20/24: containing perhaloalkyl radicals
- C08F 20/26: Esters containing oxygen in addition to the carboxy oxygen
- C08F 220/1818: {C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate}
- C08F 220/26: Esters containing oxygen in addition to the carboxy oxygen
- C08K 9/08: Ingredients agglomerated by treatment with a binding agent
- C08L 33/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C09D 133/16: Homopolymers or copolymers of esters containing halogen atoms
- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- G03F 7/2002: {with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image}
- G03F 7/2041: {in the presence of a fluid, e.g. immersion; using fluid cooling means}
- G03F 7/32: Liquid compositions therefor, e.g. developers
- G03F 7/322: {Aqueous alkaline compositions}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)

## Abstract

An actinic ray-sensitive or radiation-sensitive resin composition contains a resin (C) having a repeating unit represented by Formula (I), A pattern forming method includes a step of forming a film with the actinic ray-sensitive or radiation-sensitive resin composition, and a method of manufacturing an electronic device includes the pattern forming method, in Formula (I), Z represents a halogen atom, a group represented by R11OCH2—, or a group represented by R12OC(═O)CH2—. R11 and R12 each represent a monovalent substituent. X represents an oxygen atom or a sulfur atom. L represents a (n+1)-valent linking group. R represents a group having a group that is decomposed due to the action of an alkali developer to increase solubility in an alkali developer, n represents a positive integer.

## Claims

### Claim 1

An actinic ray-sensitive or radiation-sensitive resin composition comprising: a resin (C) having a repeating unit represented by Formula (1),
in Formula (1), Z represents a halogen atom, a group represented by R11OCH2—, or a group represented by R12OC(═O)CH2—. R11 and R12 each independently represent a monovalent substituent, X represents an oxygen atom or a sulfur atom, L represents a (n+1)-valent linking group, R represents a group having a group that is decomposed due to the action of an alkali developer to increase solubility in an alkali developer, n represents a positive integer, and in a case where n is 2 or more, a plurality of R's may be identical to or different from each other.

### Claim 2 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein in the Formula (1), R includes an electron withdrawing group.

### Claim 3 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein in the Formula (1). R includes an electron withdrawing group and L represents a linear aliphatic group or an aromatic group.

### Claim 4 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein the repeating unit represented by Formula (1) is a repeating unit represented by Formula (2) or (3),
in Formula (2), R2 represents an electron withdrawing group, L2 represents a divalent linking group, X2 represents an oxygen atom or a sulfur atom, and Z2, represents a halogen atom,
in Formula (3), R3 represents an electron withdrawing group, L3 represents a divalent linking group, X3 represents an oxygen atom or a sulfur atom, and Z3 represents a halogen atom.

### Claim 5 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein the repeating unit represented by Formula (I) is a repeating unit represented by Formula (4),
in Formula (4), 1 represents an electron withdrawing group, R5 represents a hydrogen atom, an alkyl group, or an aryl group, L4 represents a divalent linking group, X4 represents an oxygen atom or a sulfur atom, and m represents 0 or 1.

### Claim 6 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein the repeating unit represented by Formula (1) is a repeating unit represented by Formula (5),
in Formula (5), Z represents a halogen atom, a group represented by R11OCH2—, or a group represented by R12OC(═O)CH2—, R11 and R12 each independently represent a monovalent substituent, and R6 represents an electron withdrawing group.

### Claim 7 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein, in a case where an actinic ray-sensitive or radiation-sensitive film is formed, a receding contact angle of water on the actinic ray-sensitive or radiation-sensitive film is 75° or more.

### Claim 8 (depends on 1)

An actinic ray-sensitive or radiation-sensitive film formed of the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1.

### Claim 9 (depends on 1)

A pattern forming method comprising:
(i) forming an actinic ray-sensitive or radiation-sensitive film with the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1;
(ii) irradiating the actinic ray-sensitive or radiation-sensitive film with actinic rays or radiation; and
(iii) developing the actinic ray-sensitive or radiation-sensitive film irradiated with actinic ray or radiation with a developer.

### Claim 10 (depends on 9)

The pattei ming method according to claim 9, wherein the developer is an alkali developer.

### Claim 11 (depends on 9)

A method of manufacturing an electronic device, comprising: the pattern forming method according to claim 9.

### Claim 12

A compound represented by Formula (1M),
in Formula (1M), Z represents a halogen atom, a group represented by R11OCH2—, or a group represented by R12OC(═O)CH12—, R11 and R12 each independently represent a monovalent substituent, X represents an oxygen atom or a sulfur atom, L represents a (n+1)-valent linking group, R represents a group having a group that is decomposed due to the action of an alkali developer to increase solubility in an alkali developer, n represents a positive integer, and in a case where n is 2 or more, a plurality of R's may be identical to or different from each other.

### Claim 13 (depends on 12)

The compound according to claim 12, wherein in the Formula (1M), R includes an electron withdrawing group.

### Claim 14 (depends on 12)

The compound according to claim 12, wherein in the Formula (1M), R includes an electron withdrawing group and L represents a linear aliphatic group or an aromatic group.

### Claim 15

A resin having: a repeating unit represented by Formula (1),
in Formula (1), Z represents a halogen atom, a group represented by R11OCH2—, or a group represented by R12OC(═O)CH2—, R11 and R12 each independently represent a monovalent substituent, X represents an oxygen atom or a sulfur atom, L represents a (n+1)-valent linking group, R represents a group having a group that is decomposed due to the action of an alkali developer to increase solubility in an alkali developer, n represents a positive integer, and in a case where n is 2 or more, a plurality of R's may be identical to or different from each other.

### Claim 16 (depends on 15)

The resin composition according to claim 15, wherein in the Formula (1), R includes an electron withdrawing group.

### Claim 17 (depends on 15)

The resin composition according to claim 15, wherein in the Formula (1), R includes an electron withdrawing group and L represents a linear aliphatic group or an aromatic group.