Resist composition, and method of forming resist pattern

Patent metadata

Field	Value
Publication number	US-11256169-B2
Application number	US-201916421125-A
Country	US
Kind code	B2
Filing date	May 23, 2019
Priority date	May 28, 2018
Publication date	Feb 22, 2022
Grant date	Feb 22, 2022

Abstract

A resist composition containing a resin component having a structural unit containing a group which is dissociated under the action of an acid and compound represented by the general formula (bd1). In the formula (bd1), Rx1 to Rx4 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure, Ry1 to Ry2 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure, and Rz1 to Rz4 represent a hydrocarbon group or a hydrogen atom or may be mutually bonded to form a ring structure. At least one of Rx1 to Rx4, Ry1 to Ry2 and Rz1 to Rz4 has an anion group, the entire anion moiety may be an n-valent anion, and Mm+ represents an m-valent organic cation

First claim

What is claimed is:

1. A resist composition that generates an acid upon exposure and exhibits a changed solubility in a developing solution under the action of an acid, comprising:
a resin component (A1) that exhibits a changed solubility in a developing solution under the action of an acid and a compound (BD1) which is represented by the following general formula (bd1) and has an anion moiety and a cation moiety,
wherein the resin component (A1) contains the following resin component (a) or (b):
the resin component (a) having a structural unit (a0-1a) in which a polymerizable group at the W 1 site in a compound represented by the following general formula (a0-1a-1) is converted into a main; or
the resin component (b), provided that the resin component (a) is excluded, having a structural unit (a0-1b) in which a polymerizable group at the W 1 in a compound represented by the following general formula (a0-1b-1) is converted into a main chain and at least one structural unit selected from the group consisting of a structural unit (a0-2) in which a polymerizable group at the W 2 site in the compound represented by the following general formula (a0-2-1) is converted into a main chain, and a structural unit (a0-3) having a partial structure represented by the following general formula (a0-3):

wherein Rx 1 to Rx 4 each independently represent a hydrocarbon group which may have a substituent or a hydrogen atom, or two or more of Rx 1 to Rx 4 may be mutually bonded to form a ring structure; Ry 1 to Ry 2 each independently represent a hydrocarbon group which may have a substituent or a hydrogen atom, or may be mutually bonded to form a ring structure;

is a double bond or a single bond; Rz 1 to Rz 4 each independently represent, where valence allows, a hydrocarbon group which may have a substituent or a hydrogen atom, provided that two or more of Rz 1 to Rz 4 are mutually bonded to form a ring structure, provided that at least one of Rx 1 to Rx 4 , Ry 1 to Ry 2 and Rz 1 to Rz 4 has an anion group, and the entire anion moiety may be an n-valent anion; n is an integer of 1 or more; and m is an integer of 1 or more and M m+ represents an m-valent organic cation, and

wherein W 1 represents a polymerizable group-containing group; Ra 01a represents an acid dissociable group which has a carbon atom constituting a carbon-carbon unsaturated bond at the α-position of a carbon atom which is bonded to the oxy group (—O—) in the general formula (a0-1a-1); and Ra 01b represents an acid dissociable group represented by the following general formula (a01-r-1) or general formula (a01-r-2), and

wherein Ra 011 to Ra 013 each independently represent a linear or branched aliphatic hydrocarbon group, an alicyclic group having no crosslinked structure, or an aromatic hydrocarbon group; Ra 014 represents a linear or branched aliphatic hydrocarbon group having 1 to 12 carbon atoms in which some atoms may be substituted with a halogen atom or a hetero atom-containing group or an aryl group having 6 to 12 carbon atoms in which some atoms may be substituted with a halogen atom or a hetero atom-containing group; Ra 015 represents a group that forms a monocyclic aliphatic cyclic group together with a carbon atom to which Ra 014 is bonded; and * indicates a bond, and

wherein W 2 represents a polymerizable group-containing group; Wa x0 represents an (n ax0 +1)-valent aromatic cyclic group which may have a substituent; Wa x0 may form a condensed ring with W 2 ; and n ax0 is an integer of 1 to 3, and

wherein R 1 represents a fluorinated alkyl group having 1 to 12 carbon atoms; R 2 represents an organic group having 1 to 12 carbon atoms which may have a fluorine atom, or a hydrogen atom; and * indicates a bond.

2. The resist composition according to claim 1 , wherein the resin component (A1) is the resin component (a).

3. The resist composition according to claim 2 ,
wherein the compound (BD1) is an acid-generator component (B) that generates an acid upon exposure, and
wherein at least one of Rx 1 to Rx 4 , Ry 1 to Ry 2 and Rz 1 to Rz 4 has an anion group represented by the following general formula (an-1), the entire anion moiety in the general formula (bd1) is an n-valent anion, and the number of carbonyl groups in the entire anion moiety is 1 or 0:

wherein R b01d represents a fluorine atom or a fluorinated alkyl group having 1 to 5 carbon atoms; Y b01d represents a single bond or a bivalent linking group, provided that when Y b01d is a bivalent linking group, the number of carbonyl groups contained in Y b01d is 1 or 0; V b01d represents a single bond, an alkylene group or a fluorinated alkylene group; and * indicates a bond.

4. The resist composition according to claim 1 , wherein a proportion of the structural unit (a0-1a) is 20 to 80 mol % with respect to all structural units (100 mol %) constituting the resin component (A1).

5. The resist composition according to claim 2 , wherein the resin component (a) further has the structural unit (a0-3).

6. The resist composition according to claim 1 , wherein the resin component (A1) is the resin component (b) and has the structural unit (a0-1b) and the structural unit (a0-2).

7. The resist composition according to claim 6 , wherein the structural unit (a0-2) is a structural unit represented by the following general formula (a0-2-u1):

wherein R x11 , R x12 and R x13 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms; Ya x1 represents a single bond or a bivalent linking group; Wa x1 represents an (n ax1 +1)-valent aromatic cyclic group which may have a substituent, provided that Ya x1 and Wa x1 may form a condensed ring, or R x11 , Ya x1 , and Wa x1 may form a condensed ring; and n ax1 is an integer of 1 to 3.

8. The resist composition according to claim 6 , wherein a proportion of the structural unit (a0-1b) is 30 to 70 mol % with respect to all structural units (100 mol %) constituting the resin component (A1).

9. The resist composition according to claim 6 , wherein the resin component (b) further has the structural unit (a0-3).

10. The resist composition according to claim 6 ,
wherein the compound (BD1) is an acid-generator component (B) that generates an acid upon exposure, and
wherein at least one of Rx 1 to Rx 4 , Ry 1 to Ry 2 and Rz 1 to Rz 4 has an anion group represented by the following general formula (an-1), the entire anion moiety in the general formula (bd1) is an n-valent anion, and the number of carbonyl groups in the entire anion moiety is 1 or 0:

wherein R b01d represents a fluorine atom or a fluorinated alkyl group having 1 to 5 carbon atoms; Y b01d represents a single bond or a bivalent linking group, provided that when Y b01d is a bival

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Ikeda Takuya
• Michibayashi Nobuhiro
• Murata Mari
• Yamazaki Hiroto
• Arai Masatoshi
• Komuro Yoshitaka

Classifications

• C08F220/1818

  C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate · CPC title

• C09D125/18

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title

• C08F220/1812

  C12-(meth)acrylate, e.g. lauryl (meth)acrylate · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• C08F220/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title