Resist composition and method of forming resist pattern

Patent metadata

Field	Value
Publication number	US-11747726-B2
Application number	US-202016909100-A
Country	US
Kind code	B2
Filing date	Jun 23, 2020
Priority date	Jun 25, 2019
Publication date	Sep 5, 2023
Grant date	Sep 5, 2023

Abstract

A resist composition including a base component and a fluorine additive component (F), the component (F) including a copolymer having a structural unit (f1) represented by general formula (f1-1) or (f1-2), and a structural unit (f2) represented by general formula (f2-1) (in formula (f1-1) and (f2-1), R represents a hydrogen atom or the like; at least one of Raf 11 and Raf 12 , and at least one of Raf 13 and Raf 14 represents a hydrocarbon group substituted with a fluorine atom, and the total number of carbon atoms is 3 or more, provided that a hydrocarbon group forming a bridge structure is excluded; and the structural unit (f2) has a specific acid dissociable group containing an aliphatic cyclic group having no bridge structure

First claim

What is claimed is:

1. A resist composition which generates an acid upon exposure and exhibits changed solubility in a developing solution under action of the acid, the resist composition comprising:
a base component (A) which exhibits changed solubility in a developing solution under action of the acid, and
a fluorine additive component (F) which exhibits decomposability to an alkali developing solution,
the base component (A) comprising a resin component (A1) having a structural unit (a1) containing an acid decomposable group that exhibits increased polarity by the action of the acid, and a structural unit (a10) represented by general formula (a10-1) shown below,

wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Ya x1 represents a single bond or a divalent linking group; Wa x1 represents an aromatic hydrocarbon group having a valency of (n ax1 +1); and n ax1 represents an integer of 1 or more;
the fluorine additive component (F) comprising a copolymer (F1) having a structural unit (f1) represented by general formula (f1-1) shown below or general formula (f1-2) shown below, and a structural unit (f2) represented by general formula (f2-1) shown below:

wherein, in formula (f1-1), R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Raf 11 represents a divalent linking group having no acid-dissociable portion; Raf 12 represents a monovalent organic group; —O—Raf 12 represents a group capable of being dissociated by the action of a base; provided that a hydrocarbon group forming a bridge structure is excluded from Raf 11 and Raf 12 ; at least one of Raf 11 and Raf 12 is a group in which part or all of the hydrogen atoms of a hydrocarbon group have been substituted with a fluorine atom; and the total number of fluorine atoms within Raf 11 and Raf 12 is 3 or more;
in formula (f1-2), R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Raf 13 represents a divalent linking group having no acid-dissociable portion; Raf 14 represents a monovalent organic group; —C(═O)Raf 14 represents a group capable of being dissociated by the action of a base; provided that a hydrocarbon group forming a bridge structure is excluded from Raf 13 and Raf 14 ; at least one of Raf 13 and Raf 14 is a group in which part or all of the hydrogen atoms of a hydrocarbon group have been substituted with a fluorine atom; and the total number of fluorine atoms within Raf 13 and Raf 14 is 3 or more:

wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; and Raf 21 is an acid dissociable group represented by general formula (f2-r-1) or (f2-r-2) shown below:

wherein, in formula (f2-r-1), Yaf represents a carbon atom; Xaf represents a group which forms an aliphatic cyclic group together with Yaf; wherein part or all of the hydrogen atoms of the aliphatic cyclic group may be substituted; provided that Xaf and Yaf do not form an aliphatic cyclic group having a bridge structure; Raf 01 to Raf 03 each independently represents a hydrogen atom, a monovalent saturated chain hydrocarbon group of 1 to 10 carbon atoms or a monovalent saturated aliphatic cyclic hydrocarbon group of 3 to 20 carbon atoms, provided that part or all of the hydrogen atoms of the saturated chain hydrocarbon or the saturated aliphatic cyclic hydrocarbon may be substituted; two or more of Raf 01 to Raf 03 may be mutually bonded to form a ring structure; and * represents a valence bond;
in formula (f2-r-2), Yaaf represents a carbon atom; Xaaf represents a group which forms an aliphatic cyclic group together with Yaaf, wherein part or all of the hydrogen atoms of the aliphatic cyclic group may be substituted; provided that Xaaf and Yaaf do not form an aliphatic cyclic group having a bridge structure; Raf 04 represents an aromatic hydrocarbon group which may have a substituent; and * represents a valence bond.

2. The resist composition according to claim 1 , wherein the amount of the structural unit (f1) contained in the copolymer (F1), based on the combined total (100 mol %) of all structural units constituting the copolymer (F1) is 35 mol % or more.

3. The resist composition according to claim 1 , wherein the structural unit (f1) is a structural unit represented by general formula (f1-1-1) shown below or general formula (f1-2-1) shown below:

wherein, in formula (f1-1-1), R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Raf′ 11 represents a divalent, linear, branched or monocyclic hydrocarbon group having no acid-dissociable portion; Raf′ 12 represents a monovalent, linear, branched or monocyclic hydrocarbon group; —O—Raf′ 12 represents a group capable of being dissociated by the action of a base; provided that at least one of Raf′ 11 and Raf′ 12 is a group in which part or all of the hydrogen atoms of a linear, branched or monocyclic hydrocarbon group have been substituted with a fluorine atom; the total number of fluorine atoms within Raf′ 11 and Raf′ 12 is 5 or more;
in formula (f1-2-1), R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Raf′ 13 represents a divalent, linear, branched or monocyclic hydrocarbon group having no acid-dissociable portion; Raf′ 14 represents a monovalent, linear, branched or monocyclic hydrocarbon group; —C(═O)Raf′ 14 represents a group capable of being dissociated by the action of a base; provided that at least one of Raf′ 13 and Raf′ 14 is a group in which part or all of the hydrogen atoms of a linear, branched or monocyclic hydrocarbon group have been substituted with a fluorine atom; and the total number of fluorine atoms within Raf′ 13 and Raf′ 14 is 5 or more.

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

5. The method according to claim 4 , wherein the resist film is exposed to extreme ultraviolet (EUV) or electron beam (EB).

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Fukumura Yuki
• Fujii Tatsuya
• Hori Yoichi

Classifications

• G03F7/0046 Primary

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• C08F222/18

  Esters containing halogen · CPC title

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title