Resist composition and method of forming resist pattern

Patent metadata

Field	Value
Publication number	US-10101658-B2
Application number	US-201614995987-A
Country	US
Kind code	B2
Filing date	Jan 14, 2016
Priority date	Jan 16, 2015
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, the resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid generator (B) which generates acid upon exposure, the base component (A) including a resin component having a structural unit (a0) represented by general formula (a0-1) shown below, and the acid generator component (B) containing a compound having a cation moiety having an electron withdrawing group (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 represents a carbon atom; Xa represents an atomic group required to form an alicyclic hydrocarbon group with Ya; and Ra 01 represents an aromatic hydrocarbon group optionally having a substituent).

First claim

What is claimed is:

1. A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid,
the resist composition comprising a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid generator (B) which generates acid upon exposure,
the base component (A) comprising a resin component comprising a structural unit (a0) represented by general formula (a0-1) shown below, and
the acid generator component (B) comprising a compound represented by general formula (b-1), (b-2) or (b-3), having a cation moiety having an electron withdrawing group:

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 represents a carbon atom; Xa represents an atomic group required to form an alicyclic hydrocarbon group with Ya; and Ra 01 represents an aromatic hydrocarbon group optionally having a substituent,

wherein, R 101 and R 104 to R 108 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent, provided that R 104 and R 105 may be mutually bonded to form a ring; R 106 and R 107 may be mutually bonded to form a ring; R 102 represents a fluorine atom or a fluorinated alkyl group of 1 to 5 carbon atoms; Y 101 represents a divalent linking group containing an oxygen atom; V 101 to V 103 each independently represents a single bond, an alkylene group or a fluorinated alkylene group; L 101 and L 102 each independently represents a single bond or an oxygen atom; L 103 to L 105 each independently represents a single bond, —CO— or —SO 2 —; and M′ m+ represents an organic cation having a valency of m and a cation moiety having an electron withdrawing group,
wherein the cation moiety having an electron withdrawing group is represented by formula (ca-1), (ca-1-1), (ca-3) or (ca-4):

in formula (ca-1), R 202 and R 203 each independently represents an aryl group, alkyl group or alkenyl group which may have a substituent, and are mutually bonded directly or via a hetero atom, an oxygen atom or a nitrogen atom, a carbonyl group, —SO—, —SO 2 —, —SO 3 —, —COO—, —CONH— or —N(R N )—, wherein R N represents an alkyl group of 1 to 5 carbon atoms, to form a ring with the sulfur atom, R 201 represents an optionally substituted aryl group having a halogenated alkyl group as an electron withdrawing group,

in formula (ca-1-1), Rb 01 represents a halogenated alkyl group being an electron withdrawing group, Rb 02 represents an alkyl group of 1 to 5 carbon atoms, a plurality of Rb 01 and Rb 02 may be the same or different from each other, n2 represents an integer of 0 to 4, n1 represents an integer of 0 to 4; provided that at least one of n1 represents an integer of 1 to 4,

in formula (ca-3), R 206 and R 207 each independently represents an aryl group, alkyl group or alkenyl group which may have a substituent, R 210 represents an aryl group which may have a substituent, an alkyl group which may have a substituent, an alkenyl group which may have a substituent or an —SO 2 — containing cyclic group which may have a substituent, R 208 and R 209 each independently represents a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, and L 201 represents —C(═O)— or —C(═O)—O—,

in formula (ca-4), R 211 and R 212 each independently represents an aryl group, alkyl group or alkenyl group which may have a substituent, at least one of R 211 and R 212 has an electron withdrawing group, each Y 201 independently represents an arylene group, an alkylene group, or an alkenylene group, x represents 1 or 2, and W 201 represents a linking group having a valency of (x+1).

2. The resist composition according to claim 1 , wherein the resin component comprises a polymeric compound (A1) comprising the structural unit (a0) and a polymeric compound (A2) comprising a structural unit (a9) represented by general formula (a9-1) 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 91 represents a single bond or a divalent linking group; R 91 represents a hydrocarbon group optionally having a substituent; and Ya 92 represents a divalent linking group.

3. The resist composition according to claim 2 , wherein the polymeric compound (A1) further comprises a structural unit derived from hydroxystyrene or a hydroxystyrene derivative.

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

5. A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid,
the resist composition comprising a base component (A′) which exhibits changed solubility in a developing solution under action of acid and an acid diffusion control agent (D′),
the base component (A′) comprising a resin component comprising a structural unit (a0) represented by general formula (a0-1) shown below and a structural unit (a2′) derived from an acrylate ester monomer having a log P value of 0.7 or less, and
the acid diffusion control agent (D′) has an acid dissociation constant of 1.5 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; Ya represents a carbon atom; Xa represents an atomic group required to form an alicyclic hydrocarbon group with Ya; and Ra 01 represents an aromatic hydrocarbon group optionally having a substituent,
wherein the acid diffusion control agent (D′) is at least one selected from the group consisting of a compound represented by general formula (d1-1), a compound represented by general formula (d1-2) and a compound represented by general formula (d1-3):

wherein Rd 1 to Rd 4 represent a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent, provided that, the carbon atom adjacent to the sulfur atom within the Rd 2 in the formula (d1-2) has no fluorine atom bonded thereto; Yd′ represents a single bond or a divalent linking group; and M m+ each independently represents a cation having a valency of m represented by general formulas (ca-1) to (ca-4),

wherein R 201 to R 203 each independently represents an aryl group, alkyl group or alkenyl group which may have a substituent, and at least one of R 201 to R 203 has an electron withdrawing group

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Hirayama Taku
• Kawana Daisuke
• Matsumaru Shogo
• Suzuki Kenta
• Kamizono Takashi
• Yahagi Masahito
• Fujii Tatsuya

Classifications

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/322

  Aqueous alkaline compositions · CPC title

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title

• G03F7/0397 Primary

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

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title