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US 2025/0321484 A1Published application
Method for forming resist pattern and radiation-sensitive resin composition
AssigneeJsr Corporation
InventorsKazuki KASAHARA, Katsuaki NISHIKORI, Sosuke OSAWA, Miki TAMADA, Motohiro SHIRATANI
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Abstract
Provided are a method for forming a resist pattern that demonstrates excellent performance in sensitivity, resolution, etc. in an exposure step when a next-generation exposure technique is applied, and a radiation-sensitive resin composition. The method for forming a resist pattern includes step (1) of forming a resist film in which a content of a radiation-sensitive acid generator (C) is 0.1% by mass or less, step (2) of exposing the resist film to EUV or an electron beam (EB), and step (3) of developing the resist film exposed in the step (2).
Claims20
1:
- A method for forming a resist pattern, the method comprising:
- applying a radiation-sensitive resin composition (A) directly or indirectly on a substrate to form a resist film;
- exposing the resist film to EUV or an electron beam (EB);
- and
- developing the resist film exposed,
- wherein radiation-sensitive resin composition (A) comprises:
- a resin (A1) comprising a structural unit (a2) which comprises a group that dissociates due to EUV or electron beam (EB) exposure in absence of a radiation-sensitive acid generator;
- and optionally a radiation-sensitive acid generator (C), a content of the radiation-sensitive acid generator (C) in the radiation-sensitive resin composition (A) being 0.1% by mass or less based on a total amount of components of the radiation-sensitive composition (A) other than a solvent, and
- a solubility of the radiation-sensitive resin composition changes due to EUV or electron beam (EB) exposure in absence of a radiation-sensitive acid generator.
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2:
- The method according to claim 1, wherein the resist film is formed by applying a radiation-sensitive resin composition (A) directly or indirectly on a substrate, the radiation-sensitive resin composition (A) comprising:
- a solvent (B);
- and optionally the radiation-sensitive acid generator (C) which accounts for 0.1% by mass or less based on a total amount of components of the radiation-sensitive resin composition other than the solvent (B).
3:
- The method according to claim 1, wherein the resist film is formed by applying a radiation-sensitive resin composition (A) directly or indirectly on a substrate, and the radiation-sensitive resin composition (A) comprises no radiation-sensitive acid generator.
4:
- The method according to claim 1, wherein the resin (A1) changes to water-soluble or alkali-soluble due to EUV or electron beam (EB) exposure in absence of a radiation-sensitive acid generator.
5:
- The method according to claim 1, wherein in the developing of the resist film, the resist film is developed with an organic solvent to form a negative tone pattern.
6:
- The method according to claim 1, wherein in the developing of the resist film, the resist film is developed with an alkaline developer to form a positive tone pattern.
7:
- The method according to claim 1, wherein the structural unit (a2) comprises a tertiary alkyl ester moiety.
8:
- The method according to claim 1, wherein the structural unit (a2) is represented by formula (2):
- wherein, in the formula (2), R7 is a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group;
- R8 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms;
- R9 and R10 are each independently a monovalent chain hydrocarbon group having 1 to 20 carbon atoms which is substituted or unsubstituted with a fluorine atom, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms which is substituted or unsubstituted with a fluorine atom, or a monovalent aromatic hydrocarbon group having 5 to 20 carbon atoms, or taken together represent a divalent alicyclic group having 3 to 20 carbon atoms that is substituted or unsubstituted with a fluorine atom together with a carbon atom to which R9 and R10 are bonded;
- any of R8 to R10 and/or the alicyclic group when present optionally have an unsaturated bond;
- and
- two or more of R8 to R10 optionally form one alicyclic structure.
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9:
- The method according to claim 1, wherein the resin (A1) further comprises a structural unit comprising a phenolic hydroxy group which is represented by formula (af):
- wherein, in the formula (af), RAF1 is a hydrogen atom or a methyl group;
- LAF is a single bond, —COO—, —O—, or —CONH—;
- RAF2 is a monovalent organic group having 1 to 20 carbon atoms;
- nf1 is an integer of 0 to 3, wherein when nf1 is 2 or 3, the plurality of RAF2s are same or different;
- nf2 is an integer of 1 to 3, provided that nf1+nf2 is 5 or less, and naf is an integer of 0 to 2.
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10:
- A method for processing a substrate, the method comprising forming a pattern on a substrate using the resist pattern formed by the method according to claim 1 as a mask.
11:
- A method for manufacturing a metal film pattern, the method comprising forming a patterned metal film using the resist pattern formed by the method according to claim 1 as a mask.
12:
- A radiation-sensitive resin composition comprising:
- (A2) a resin comprising a structural unit (a2) which comprises a group that dissociates due to EUV or electron beam (EB) exposure in absence of a radiation-sensitive acid generator;
- (B) a solvent;
- and
- (C) a radiation-sensitive acid generator,
- wherein in the radiation-sensitive resin composition, the radiation-sensitive acid generator (C) accounts for 0.1% by mass or less based on a total amount of components of the radiation-sensitive composition other than the solvent (B).
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13:
- The radiation-sensitive resin composition according to claim 12, wherein the structural unit (a2) comprises a tertiary alkyl ester moiety.
14:
- The radiation-sensitive resin composition according to claim 12, wherein the resin (A2) further comprises a structural unit comprising a phenolic hydroxy group which is represented by formula (af):
- wherein, in the formula (af), RAF1 is a hydrogen atom or a methyl group;
- LAF is a single bond, —COO—, —O—, or —CONH—;
- RAF2 is a monovalent organic group having 1 to 20 carbon atoms;
- nf1 is an integer of 0 to 3, wherein when nf1 is 2 or 3, the plurality of RAF2s are same or different;
- nf2 is an integer of 1 to 3, provided that nf1+nf2 is 5 or less, and naf is an integer of 0 to 2.
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15:
- The radiation-sensitive resin composition according to claim 12, wherein the resin (A2) dissociates due to EUV or electron beam (EB) exposure to form a carboxylic acid structure.
16:
- The radiation-sensitive resin composition according to claim 12, wherein the structural unit (a2) is represented by formula (2):
- wherein, in the formula (2), R7 is a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group;
- R8 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms;
- R9 and R10 are each independently a monovalent chain hydrocarbon group having 1 to 20 carbon atoms which is substituted or unsubstituted with a fluorine atom, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms which is substituted or unsubstituted with a fluorine atom, or a monovalent aromatic hydrocarbon group having 5 to 20 carbon atoms, or taken together represent a divalent alicyclic group having 3 to 20 carbon atoms that is substituted or unsubstituted with a fluorine atom together with a carbon atom to which R9 and R10 are bonded;
- any of R8 to R10 and/or the alicyclic group when present optionally have an unsaturated bond;
- and
- two or more of R8 to R10 optionally form one alicyclic structure.
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17:
- A radiation-sensitive resin composition consisting of:
- (A2) a resin comprising a structural unit (a2) which comprises a group that dissociates due to EUV or electron beam (EB) exposure in absence of a radiation-sensitive acid generator;
- and
- (B) a solvent.
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18:
- The radiation-sensitive resin composition according to claim 17, wherein the structural unit (a2) comprises a tertiary alkyl ester moiety.
19:
- The radiation-sensitive resin composition according to claim 17, wherein the structural unit (a2) is represented by formula (2):
- wherein, in the formula (2), R7 is a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group;
- R8 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms;
- R9 and R10 are each independently a monovalent chain hydrocarbon group having 1 to 20 carbon atoms which is substituted or unsubstituted with a fluorine atom, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms which is substituted or unsubstituted with a fluorine atom, or a monovalent aromatic hydrocarbon group having 5 to 20 carbon atoms, or taken together represent a divalent alicyclic group having 3 to 20 carbon atoms that is substituted or unsubstituted with a fluorine atom together with a carbon atom to which R9 and R10 are bonded;
- any of R8 to R10 and/or the alicyclic group when present optionally have an unsaturated bond;
- and
- two or more of R8 to R10 optionally form one alicyclic structure.
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20:
- The radiation-sensitive resin composition according to claim 17, wherein the resin (A2) further comprises a structural unit comprising a phenolic hydroxy group which is represented by formula (af):
- wherein, in the formula (af), RAF1 is a hydrogen atom or a methyl group;
- LAF is a single bond, —COO—, —O—, or —CONH—;
- RAF2 is a monovalent organic group having 1 to 20 carbon atoms;
- nf1 is an integer of 0 to 3, wherein when nf1 is 2 or 3, the plurality of RAF2s are same or different;
- nf2 is an integer of 1 to 3, provided that nf1+nf2 is 5 or less, and naf is an integer of 0 to 2.
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