# US 2018/0024433 A1 · Resist composition, method for forming resist pattern, and polymer compound

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- Number: US 2018/0024433 A1
- Document ID: US20180024433A1
- Status: Published application
- Kind: A1
- Application number: 15/651,177
- Filed: 2017-07-17
- Published: 2018-01-25
- Earliest claimed: 2016-07-22
- Assignees: Tokyo Ohka Kogyo Co., Ltd.
- Applicants: Tokyo Ohka Kogyo Co., Ltd.
- Inventors: Yoshitaka KOMURO; Masatoshi ARAI; Koshi ONISHI; KhanhTin NGUYEN; Takaya MAEHASHI
- Web page: https://patentgrep.com/patent/US20180024433A1

## CPC

- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- C08F 18/02: Esters of monocarboxylic acids
- C08F 222/10: Esters
- G03F 7/0382: {the macromolecular compound being present in a chemically amplified negative photoresist composition}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/30: Imagewise removal using liquid means
- H10P 95/00: Generic processes or apparatus for manufacture or treatments not covered by the other groups of this subclass
- 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
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

A resist composition which generates an acid upon exposure and whose solubility on a developing solution changes under the action of the acid, including a polymer compound having units represented by formulas (a0-1), (a0-2), and (a0-3) in an amount of 0 to 10 mol %. In the formulas, R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va01 and Va03 are a divalent hydrocarbon group, na01 and na03 each are an integer of 0 to 2, Ra0″ is a specific acid dissociable group, Va02 is a divalent linking group containing a hetero atom or a single bond, Ra07 is a monovalent organic group, na021 is an integer of 0 to 3, and na022 is an integer of 1 to 3.

## Claims

### Claim 1

A resist composition which generates an acid upon exposure and whose solubility in a developing solution changes under the action of an acid, the composition comprising:
a base material (A) whose solubility in the developing solution changes under the action of an acid and which comprises a polymer compound (A1) having a structural unit (a01), a structural unit (a02), and a structural unit (a03), wherein
a ratio of the structural unit (a03) in the polymer compound (A1) is greater than 0 mol % and equal to or less than 10 mol % with respect to the total of all the structural units constituting the polymer compound (A1),
the structural unit (a01) is represented by general formula (a0-1) shown below:
wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va01 is a divalent hydrocarbon group which may have an ether bond, na01 is an integer of 0 to 2, and Ra0″ is an acid dissociable group represented by general formula (a0-r1-1), (a0-r1-2), or (a0-r1-3) shown below:
wherein in general formula (a0-r1-1), Ya0 represents a carbon atom, Xa0 is a group which forms an alicyclic hydrocarbon group together with Ya0, Ra0 is an aromatic hydrocarbon group which may have a substituent, or a group represented by general formula (a0-f1) shown below:
wherein Ra01 to Ra03 are each independently an aliphatic hydrocarbon group which may have a substituent, or a hydrogen atom, and two or more of Ra01 to Ra03 may be bonded to each other to form a cyclic structure;
in general formula (a0-r1-2), Ya00 represents a carbon atom, Xa00 is a group which forms a condensed ring of an alicyclic hydrocarbon group and an aromatic hydrocarbon group together with Ya00, and Ra00 is an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group which may have a substituent, or a group represented by general formula (a0-f1) shown above;
in general formula (a0-r1-3), Ra04 and Ra05 are each independently a monovalent chain saturated hydrocarbon group having 1 to 10 carbon atoms or a hydrogen atom, at least one hydrogen atom of the chain saturated hydrocarbon group may be substituted, and Ra06 is an aromatic hydrocarbon group which may have a substituent; and
a symbol of * represents a bond;
the structural unit (a02) is represented by general formula (a0-2) shown below:
wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va02 is a divalent linking group containing a heteroatom, or a single bond, Ra07 is a monovalent organic group, na021 is an integer of 0 to 3, and na022 is an integer of 1 to 3; and
the structural unit (a03) is represented by general formula (a0-3) shown below:
wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va03 is a divalent hydrocarbon group which may have an ether bond, and na03 is an integer of 0 to 2.

### Claim 2 (depends on 1)

The resist composition according to claim 1, wherein Ra0″ in general formula (a0-1) is an acid dissociable group represented by general formula (a0-r1-1), and the total number of the carbon atoms contained in Ya0, Xa0, and Ra0 is 11 or less.

### Claim 3 (depends on 1)

A method for forming a resist pattern, comprising:
forming a resist film on a support by using the resist composition according to claim 1;
exposing the resist film; and
developing the exposed resist film to form a resist pattern.

### Claim 4 (depends on 3)

The method for forming a resist pattern according to claim 3, wherein the resist film is exposed to extreme ultraviolet ray (EUV) or an electron beam (EB).

### Claim 5

A polymer compound comprising a structural unit (a01), a structural unit (a02), and a structural unit (a03), wherein
a ratio of the structural unit (a03) is greater than 0 mol % and equal to or less than 10 mol % with respect to the total of the entire structural units constituting the polymer compound;
the structural unit (a01) is represented by general formula (a0-1) shown below:
wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va01 is a divalent hydrocarbon group which may have an ether bond, na01 is an integer of 0 to 2, and Ra0″ is an acid dissociable group represented by general formula (a0-r1-1), (a0-r1-2), or (a0-r1-3) shown below:
wherein in general formula (a0-r1-1), Ya0 represents a carbon atom, Xa0 is a group which forms an alicyclic hydrocarbon group together with Ya0, Ra0 is an aromatic hydrocarbon group which may have a substituent, or a group represented by general formula (a0-f1) shown below:
wherein Ra01 to Ra03 are each independently an aliphatic hydrocarbon group which may have a substituent, or a hydrogen atom, and two or more of Ra01 to Ra03 may be bonded to each other to form a cyclic structure;
in general formula (a0-r1-2), Ya00 represents a carbon atom, Xa00 is a group which forms a condensed ring of an alicyclic hydrocarbon group and an aromatic hydrocarbon group together with Ya00, and Ra00 is an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group which may have a substituent, or a group represented by general formula (a0-f1) shown above;
in general formula (a0-r1-3), Ra04 and Ra05 are each independently a monovalent chain saturated hydrocarbon group having 1 to 10 carbon atoms or a hydrogen atom, at least one hydrogen atom of the chain saturated hydrocarbon group may be substituted, and Ra06 is an aromatic hydrocarbon group which may have a substituent; and
a symbol of * represents a bond;
the structural unit (a02) is represented by general formula shown below:
wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va02 is a divalent linking group containing a heteroatom, or a single bond, Ra07 is a monovalent organic group, na021 is an integer of 0 to 3, and na022 is an integer of 1 to 3; and
the structural unit (a03) is represented by general formula (a0-3) shown below:
wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va03 is a divalent hydrocarbon group which may have an ether bond, and na03 is an integer of 0 to 2.

### Claim 6 (depends on 5)

The polymer compound according to claim 5, wherein Ra0″ in general formula (a0-1) is an acid dissociable group represented by general formula (a0-r1-1), and the total number of the carbon atoms contained in Ya0, Xa0, and Ra0 is 11 or less.