# US 2014/0193749 A1 · Pattern-forming method, electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition, resist film, manufacturing method of electronic device using them and electronic device

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- Number: US 2014/0193749 A1
- Document ID: US20140193749A1
- Status: Published application
- Kind: A1
- Application number: 14/207,867
- Filed: 2014-03-13
- Published: 2014-07-10
- Earliest claimed: 2011-09-15
- Assignees: FUJIFILM Corporation
- Applicants: Fujifilm Corporation
- Inventors: Hiroo TAKIZAWA; Hideaki TSUBAKI; Shuji HIRANO
- Web page: https://patentgrep.com/patent/US20140193749A1

## CPC

- C08F 212/24: {Phenols or alcohols}
- G03F 7/004: Photosensitive materials (G03F7/12, G03F7/14 take precedence)
- G03F 7/0041: {providing an etching agent upon exposure (G03F7/075 takes precedence; photolytic halogen compounds G03F7/0295)}
- G03F 7/038: Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021)
- G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- 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 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- G03F 7/2037: {Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation}
- G03F 7/2059: {using a scanning corpuscular radiation beam, e.g. an electron beam}
- G03F 7/325: {Non-aqueous compositions}
- H01J 37/3174: {Particle-beam lithography, e.g. electron beam lithography}
- C08F 12/20: Fluorine
- C08F 12/24: Phenols or alcohols
- C08F 212/20: {Fluorine}
- C08F 212/32: containing two or more rings
- 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)
- H01J: ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS (spark-gaps H01T; electric arc lamps H05B31/00; particle accelerators H05H)

## Abstract

A pattern-forming method includes in this order: step (1) of forming a film with an electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition that contains (A) a resin having an acid-decomposable repeating unit and capable of decreasing a solubility of the resin (A) in a developer containing an organic solvent by an action of an acid, (B) a compound capable of generating an acid upon irradiation with an electron beam or extreme ultraviolet radiation and (C) a solvent; step (2) of exposing the film with an electron beam or extreme ultraviolet radiation; and step (4) of forming a negative pattern by development of the film with a developer containing an organic solvent after the exposing of the film, wherein a content of the compound (B) is 21% by mass to 70% by mass on the basis of all solids content of the composition.

## Claims

### Claim 1

A pattern-forming method, comprising in this order:
step (1) of forming a film with an electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition that contains (A) a resin having an acid-decomposable repeating unit and capable of decreasing a solubility of the resin (A) in a developer containing an organic solvent by an action of an acid, (B) a compound capable of generating an acid upon irradiation with an electron beam or extreme ultraviolet radiation and (C) a solvent;
step (2) of exposing the film with an electron beam or extreme ultraviolet radiation; and
step (4) of forming a negative pattern by development of the film with a developer containing an organic solvent after the exposing of the film,
wherein a content of the compound (B) is 21% by mass to 70% by mass on the basis of all solids content of the composition.

### Claim 2 (depends on 1)

The pattern-forming method according to claim 1,
wherein the content of the compound (B) is 31% by mass to 60% by mass on the basis of all solids content of the composition.

### Claim 3 (depends on 1)

The pattern-forming method according to claim 1,
wherein the resin (A) further has a repeating unit having a polar group.

### Claim 4 (depends on 3)

The pattern-forming method according to claim 3,
wherein the polar group is selected from the group consisting of a hydroxyl group, a cyano group, a lactone group, a carboxylic acid group, a sulfonic acid group, an amido group, a sulfonamido group, an ammonium group, a sulfonium group and a group obtained by combining two or more of the above groups.

### Claim 5 (depends on 1)

The pattern-forming method according to claim 1,
wherein the resin (A) further has a repeating unit having an acid group.

### Claim 6 (depends on 5)

The pattern-forming method according to claim 5,
wherein the acid group is a phenolic hydroxyl group, a carboxylic acid group, a sulfonic acid group, a fluorinated alcohol group, a sulfonamido group, a sulfonylimido group, an (alkylsulfonyl)(alkylcarbonyl)methylene group, an (alkylsulfonyl)(alkylcarbonyl)imido group, a bis(alkylcarbonyl)methylene group, a bis(alkylcarbonyl)imido group, a bis(alkylsulfonyl)methylene group, a bis(alkylsulfonyl)imido group, a tris-(alkylcarbonyl)methylene group or a tris(alkylsulfonyl)methylene group.

### Claim 7 (depends on 1)

The pattern-forming method according to claim 1,
wherein a content of a repeating unit represented by the following formula (I) to all repeating units in the resin (A) is 4 mol % or less:
wherein each of R41, R42 and R43 independently represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, and R42 may be bonded to Ar4 to form a ring, and in this case, R42 represents a single bond or an alkylene group;
X4 represents a single bond, —COO— or —CONR64—, and R64 represents a hydrogen atom or an alkyl group;
L4 represents a single bond or an alkylene group;
Ar4 represents an (n+1)-valent aromatic ring group, and when Ar4 forms a ring together with R42, Ar4 represents an (n+2)-valent aromatic ring group; and
n represents an integer of 1 to 4.

### Claim 8 (depends on 1)

The pattern-forming method according to claim 1, which is a method for forming a semiconductor fine circuit.

### Claim 9 (depends on 1)

An electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition, which is used for the pattern-forming method according to claim 1.

### Claim 10 (depends on 9)

A resist film, which is formed with the electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition according to claim 9.

### Claim 11 (depends on 1)

A manufacturing method of an electronic device, comprising:
the pattern-forming method according to claim 1.

### Claim 12 (depends on 11)

An electronic device, which is manufactured by the manufacturing method of an electronic device according to claim 11.