# US 8,771,921 B2 · Negative resist composition, method of forming resist pattern and polymeric compound

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- Number: US 8,771,921 B2
- Document ID: US8771921B2
- Status: Granted
- Kind: B2
- Application number: 13/410,893
- Filed: 2012-03-02
- Published: 2012-06-28
- Granted: 2014-07-08
- Earliest claimed: 2008-07-07
- Assignees: Tokyo Ohka Kogyo Co., Ltd.
- Applicants: Abe Sho; Shiono Daiju; Hirano Tomoyuki; Dazai Takahiro
- Inventors: Abe Sho; Shiono Daiju; Hirano Tomoyuki; Dazai Takahiro
- Web page: https://patentgrep.com/patent/US8771921B2

## CPC

- G03F 7/0382: {the macromolecular compound being present in a chemically amplified negative photoresist composition}
- C08F 12/20: Fluorine
- C08F 12/22: Oxygen
- C08F 212/20: {Fluorine}
- C08F 212/22: {Oxygen}
- C08F 212/32: containing two or more rings
- C08F 220/24: containing perhaloalkyl radicals
- C08F 226/02: by a single or double bond to nitrogen
- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- G03F 7/2041: {in the presence of a fluid, e.g. immersion; using fluid cooling means}
- G03F 7/30: Imagewise removal using liquid means
- G03F 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)}
- C08F 220/06: Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
- C08F 220/281: {and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate}
- C08F 220/301: {and one oxygen in the alcohol moiety}
- C08F 220/385: {and containing nitrogen}
- Y10S 430/108: Polyolefin or halogen containing
- Y10S 430/111: Polymer of unsaturated acid or ester
- 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
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A negative resist composition including an alkali-soluble resin component (A), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C), the alkali-soluble resin component (A) including a polymeric compound (F) having a structural unit (f1) containing a base dissociable group and a structural unit (f2) containing a cross-linking group-containing group.

## Claims

### Claim 1

A negative resist composition comprising an alkali-soluble resin component (A), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C),
said alkali-soluble resin component (A) comprising a polymeric compound (F) having a structural unit (f1) containing a base dissociable group represented by formula (II-1) or (II-2) shown below and a structural unit (f2) containing a cross-linking group-containing group:
wherein each R2 independently represents a fluorinated saturated hydrocarbon group or a fluorinated, unsaturated hydrocarbon group.

### Claim 2 (depends on 1)

The negative resist composition according to claim 1, wherein R2 represents a linear or branched fluorinated alkyl group.

### Claim 3 (depends on 1)

The negative resist composition according to claim 1, wherein R2 is a group represented by general formula (III-1) or (III-2) shown below:
wherein R41′ represents an unsubstituted alkylene group of 1 to 9 carbon atoms, and R42′ represents a fluorinated alkyl group of 1 to 9 carbon atoms, with the provision that the total number of carbon atoms of R41′ and R42′ is no more than 10; and each of R71 to R73 independently represents a linear alkyl group of 1 to 5 carbon atoms, with the provision that at least one of R71 to R73 represents an alkyl group having a fluorine atom.

### Claim 4 (depends on 1)

The negative resist composition according to claim 1, wherein said structural unit (f1) is a structural unit represented by general formula (f1-1) or (f1-2) shown below:
wherein each R independently represents a hydrogen atom, a lower alkyl group of 1 to 5 carbon atoms or a halogenated lower alkyl group of 1 to 5 carbon atoms; X represents a divalent organic group; Aaryl represents an aromatic cyclic group which may have a substituent; X01 represents a single bond or a divalent linking group; and each R2 independently represents an organic group having a fluorine atom.

### Claim 5 (depends on 1)

The negative resist composition according to claim 1, wherein said structural unit (f2) is at least one structural unit selected from the group consisting of structural units containing a group represented by general formulas (f2-1), (f2-2) and (f2-3) shown below:
wherein Q11 represents an alkylene group which may have an ether bond; Q12 represents a divalent linking group; Q13 represents —SO2— or —C(═O)—; and Q14 represents an aromatic cyclic group.

### Claim 6 (depends on 1)

The negative resist composition according to claim 1, wherein said cross-linking component (C) is at least one type of cross-linker selected from the group consisting of melamine-based cross-linkers, urea-based cross-linkers, alkylene urea-based cross-linkers, glycoluril-based cross-linkers and epoxy-based cross-linkers.

### Claim 7 (depends on 1)

The negative resist composition according to claim 1, further comprising a nitrogen-containing organic compound (D).

### Claim 8 (depends on 1)

A method of forming a resist pattern, comprising: applying a negative resist composition according to claim 1 to a substrate to form a resist film, subjecting said resist film to exposure, and subjecting said resist film to alkali developing to form a resist pattern.

### Claim 9

A polymeric compound comprising a structural unit (f1) represented by general formula (f1-1) or (f1-2) shown below and a structural unit (f2) containing a cross-linking group-containing group:
wherein each R independently represents a hydrogen atom, a lower alkyl group of 1 to 5 carbon atoms or a halogenated lower alkyl group of 1 to 5 carbon atoms; X represents a divalent organic group; Aaryl represents an aromatic cyclic group which may have a substituent; X01 represents a single bond or a divalent linking group; and each R2 independently represents an organic group having a fluorine atom.

### Claim 10 (depends on 9)

The polymeric compound according to claim 9, wherein R2 represents a linear or branched fluorinated alkyl group.

### Claim 11 (depends on 9)

The polymeric compound according to claim 9, wherein R2 is a group represented by general formula (III-1) or (III-2) shown below:
wherein R41′ represents an unsubstituted alkylene group of 1 to 9 carbon atoms, and R42′ represents a fluorinated alkyl group of 1 to 9 carbon atoms, with the provision that the total number of carbon atoms of R41′ and R42′ is no more than 10; and each of R71 to R73 independently represents a linear alkyl group of 1 to 5 carbon atoms, with the provision that at least one of R71 to R73 represents an alkyl group having a fluorine atom.

### Claim 12 (depends on 9)

The polymeric compound according to claim 9, wherein said structural unit (f2) is at least one structural unit selected from the group consisting of structural units containing a group represented by general formulas (f2-1), (f2-2) or (f2-3) shown below:
wherein Q11 represents an alkylene group which may have an ether bond; Q12 represents a divalent linking group; Q13 represents —SO2— or —C(═O)—; and Q14 represents an aromatic cyclic group.