# US 2026/0211326 A1 · Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, and method for producing electronic device

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- Number: US 2026/0211326 A1
- Document ID: US20260211326A1
- Status: Published application
- Kind: A1
- Application number: 19/572,281
- Filed: 2026-03-19
- Published: 2026-07-23
- Earliest claimed: 2023-09-29
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Hironori Oka; Aina Shibuya; Yoichi Nishida; Masafumi Kojima; Satomi Takahashi; Hideaki Tsubaki; Keisuke Ushirogata
- Web page: https://patentgrep.com/patent/US20260211326A1

## CPC

- G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- G03F 7/0395: {the macromolecular compound having a backbone with alicyclic moieties}
- C08F 12/02: Monomers containing only one unsaturated aliphatic radical
- C08F 20/10: Esters
- G03F 7/004: Photosensitive materials (G03F7/12, G03F7/14 take precedence)
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- 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 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- G03F 7/2022: {Multi-step exposure, e.g. hybrid; backside exposure; blanket exposure, e.g. for image reversal; edge exposure, e.g. for edge bead removal; corrective exposure}
- G03F 7/2041: {in the presence of a fluid, e.g. immersion; using fluid cooling means}
- G03F 7/322: {Aqueous alkaline compositions}
- G03F 7/70033: {by plasma extreme ultraviolet [EUV] sources}
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

An actinic ray-sensitive or radiation-sensitive resin composition contains a resin having a repeating unit and a solvent, the repeating unit includes a cation having a specified structure and an anion bonded to the molecular chain of the resin, and the content of the repeating unit relative to the total content of resins contained in the actinic ray-sensitive or radiation-sensitive resin composition is 40 mass % or more.

## Claims

### Claim 1

An actinic ray-sensitive or radiation-sensitive resin composition comprising a resin (X) having a repeating unit (u1), and a solvent,
wherein the repeating unit (u1) includes at least one cation selected from the group consisting of a cation represented by the following formula (CT-1) and a cation represented by the following formula (CT-2), and an anion bonded to a molecular chain of the resin (X),
a content of the repeating unit (u1) relative to a total content of resins contained in the actinic ray-sensitive or radiation-sensitive resin composition is 40 mass % or more,
wherein, in the formula (CT-1) and the formula (CT-2),
R3 and R4 each independently represent an organic group, a hydroxy group, a mercapto group, an amino group, a nitro group, a phosphino group, a silyl group, or a halogen atom; when a plurality of R3 are present, the plurality of R3 may be bonded together, directly by a single bond or via a linking group, to form a ring; when a plurality of R4 are present, the plurality of R4 may be bonded together, directly by a single bond or via a linking group, to form a ring,
R5 and R6 each independently represent an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group, or a heteroaryl group; when R5 and R6 include a methylene group, at least one of the methylene groups may be substituted with a divalent heteroatom-containing group; R5 and R6 may be bonded together, directly by a single bond or via any one selected from the group consisting of an oxygen atom, a sulfur atom, and an alkylene group, to form a ring,
R7 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group, or a heteroaryl group,
R8 and R9 each independently represent a hydrogen atom, an organic group, a hydroxy group, a mercapto group, an amino group, a nitro group, a phosphino group, a silyl group, or a halogen atom, or R8 and R9 are bonded together to represent a single bond or a divalent linking group,
R10 and R11 each independently represent an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group, or a heteroaryl group; when R10 and R11 include a methylene group, at least one of the methylene groups may be substituted with a divalent heteroatom-containing group; R10 and R11 may be bonded together, directly by a single bond or via any one selected from the group consisting of an oxygen atom, a sulfur atom, and an alkylene group, to form a ring,
Y1, Y2, Y3, and Y4 each independently represent an oxygen atom or a sulfur atom,
L1 represents an alkylene group, a cycloalkylene group, an alkenylene group, a cycloalkenylene group, an arylene group, a heteroarylene group, a linking group in which at least two groups selected from the group consisting of an alkylene group, a cycloalkylene group, an alkenylene group, a cycloalkenylene group, an arylene group, and a heteroarylene group are bonded together via at least one selected from the group consisting of a single bond, an oxygen atom, a sulfur atom, and a nitrogen atom-containing group, or a single bond,
L2 and L3 each independently represent a single bond, an alkenylene group having 2 carbon atoms, an alkynylene group having 2 carbon atoms, a carbonyl group, a sulfinyl group, or a sulfonyl group,
a and b each independently represent an integer of 1 to 3,
when a represents 1, c represents an integer of 0 to 3,
when a represents 2, c represents an integer of 0 to 5,
when a represents 3, c represents an integer of 0 to 7,
when b represents 1, d represents an integer of 0 to 4, provided that d+f is an integer of 0 to 4,
when b represents 2, d represents an integer of 0 to 6, provided that d+f is an integer of 0 to 6,
when b represents 3, d represents an integer of 0 to 8, provided that d+f is an integer of 0 to 8,
e represents 0 or 1, f represents an integer of 0 to 4, provided that e+f is an integer of 1 to 4,
in the formula (CT-1),
R1 and R2 each independently represent an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group, or a heteroaryl group; when R1 and R2 include a methylene group, at least one of the methylene groups may be substituted with a divalent heteroatom-containing group,
at least two of R1, R2, and the aromatic ring to which L1 is bonded may be bonded together, directly by a single bond or via any one selected from the group consisting of an oxygen atom, a sulfur atom, a nitrogen atom-containing group, and a methylene group, to form a ring,
in the formula (CT-2),
R12 represents an aryl group or a heteroaryl group, and
R12 and the aromatic ring to which L1 is bonded may be bonded together, directly by a single bond or via any one selected from the group consisting of an oxygen atom, a sulfur atom, a nitrogen atom-containing group, and a methylene group, to form a ring.

### Claim 2

An actinic ray-sensitive or radiation-sensitive resin composition comprising a resin (X) having a repeating unit (u1), and a solvent,
wherein the repeating unit (u1) includes at least one cation and an anion that is bonded to a molecular chain of the resin (X),
the cation undergoes a structural change by action of an acid, and a structure of the cation after the structural change has a larger peak area in an absorption spectrum for light having wavelengths of 300 nm to 450 nm than a peak area in an absorption spectrum of the structure of the cation before the structural change for light having wavelengths of 300 nm to 450 nm, and
a content of the repeating unit (u1) relative to a total content of resins contained in the actinic ray-sensitive or radiation-sensitive resin composition is 40 mass % or more.

### Claim 3

An actinic ray-sensitive or radiation-sensitive resin composition comprising a resin (X) having a repeating unit (u1), and a solvent,
wherein the repeating unit (u1) includes at least one cation and an anion that is bonded to a molecular chain of the resin (X),
the cation undergoes a structural change by action of an acid to generate a ketone group, and
a content of the repeating unit (u1) relative to a total content of resins contained in the actinic ray-sensitive or radiation-sensitive resin composition is 40 mass % or more.

### Claim 4 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein the repeating unit (u1) is a repeating unit that generates an acid upon irradiation with an actinic ray or a radiation.

### Claim 5 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, satisfying at least one of the following condition (i) or the following condition (ii):
Condition (i): the actinic ray-sensitive or radiation-sensitive resin composition contains an acid diffusion control agent that is a compound different from the resin (X), and
Condition (ii): the resin (X) has a repeating unit having acid diffusion control ability.

### Claim 6 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein the content of the repeating unit (u1) relative to the total content of resins contained in the actinic ray-sensitive or radiation-sensitive resin composition is 60 mass % or more.

### Claim 7 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein the content of the repeating unit (u1) relative to the total content of resins contained in the actinic ray-sensitive or radiation-sensitive resin composition is 80 mass % or more.

### Claim 8 (depends on 1)

A resist film formed with the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1.

### Claim 9 (depends on 1)

A pattern forming method comprising: forming, on a substrate, a resist film with the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1; irradiating the resist film with a first actinic ray or radiation; irradiating, with a second actinic ray or radiation, the resist film after the irradiating with the first actinic ray or radiation; and developing, with a developer, the resist film after the irradiating with the second actinic ray or radiation.

### Claim 10 (depends on 9)

The pattern forming method according to claim 9, wherein a wavelength of the first actinic ray or radiation is shorter than a wavelength of the second actinic ray or radiation.

### Claim 11 (depends on 10)

The pattern forming method according to claim 10, wherein the first actinic ray or radiation is an electron beam or extreme ultraviolet rays.

### Claim 12 (depends on 9)

The pattern forming method according to claim 9, wherein the irradiating with the first actinic ray or radiation generates a first active species in the resist film, the first active species causes a structural change of the cation, and the irradiating with the second actinic ray or radiation generates a second active species from the cation having undergone the structural change.

### Claim 13 (depends on 9)

The pattern forming method according to claim 9, wherein the developer is an alkaline aqueous solution.

### Claim 14 (depends on 9)

The pattern forming method according to claim 9, wherein the developer is an organic solvent.

### Claim 15 (depends on 9)

A method for producing an electronic device, the method comprising the pattern forming method according to claim 9.