Radiation-sensitive resin composition and method for forming resist pattern

Patent metadata

Field	Value
Publication number	US-11747725-B2
Application number	US-201815953860-A
Country	US
Kind code	B2
Filing date	Apr 16, 2018
Priority date	Apr 17, 2017
Publication date	Sep 5, 2023
Grant date	Sep 5, 2023

Abstract

A radiation-sensitive resin composition includes: a resin including a structure unit having an acid-dissociable group; a radiation-sensitive acid generator; and a solvent. The radiation-sensitive acid generator includes at least two of compounds represented by formulae (1) to (3), provided that the compound represented by formula (1) and the compound represented by formula (3) within the scope of the compound represented by formula (2) are excluded. In the formulae (1) to (3), R1, R2 and R3 are each independently a group having a cyclic structure; X11, X12, X21, X22, X31 and X32 are each independently a hydrogen atom, a fluorine atom, or a fluorinated hydrocarbon group, provided that both X11 and X12, both X21 and X22, and both X31 and X32 are not a hydrogen atom, respectively.

First claim

What is claimed is:

1. A radiation-sensitive resin composition, comprising:
a base resin comprising a structure unit having an acid-dissociable group, a content of the structural unit in the base resin being 30-75 mol %;
a radiation-sensitive acid generator;
an acid diffusion controlling agent;
a fluorine-containing resin having a higher content by mass of fluorine atoms than the base resin; and
a solvent which is at least one solvent selected from the group consisting of iso-propanol, 4-methyl-2-pentanol, 3-methoxybutanol, n-hexanol, 2-ethylhexanol, furfuryl alcohol, cyclohexanol, 3,3,5-trimethylcyclohexanol, ethylene glycol, 1,2-propylene glycol, 2-methyl-2,4-pentanediol, 2,5-hexanediol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, a partially etherized polyhydric alcohol-based solvent in which a part of hydroxy groups in the polyhydric alcohol is etherized, an ether-based solvent, acetone, butanone, methyl-iso-butyl ketone, cyclopentanone, cyclohexanone, methylcyclohexanone, 2,4-pentanedione, acetonylacetone, acetophenone, an amide-based solvent, an ester-based solvent, and a hydrocarbon-based solvent,
wherein the radiation-sensitive acid generator comprises:
a second compound which is at least one compound selected from the group consisting of a compound represented by formula (2-1), a compound represented by formula (2-2), a compound represented by formula (2-3), a compound represented by formula (2-4), a compound represented by formula (2-5), a compound represented by formula (2-6), a compound represented by formula (2-7), a compound represented by formula (2-8), a compound represented by formula (2-9), a compound represented by formula (2-10), a compound represented by formula (2-11), and a compound represented by formula (2-12);
a third compound which is at least one compound selected from the group consisting of a compound represented by formula (3-1), a compound represented by formula (3-2), a compound represented by formula (3-3), a compound represented by formula (3-4), a compound represented by formula (3-5), a compound represented by formula (3-6), a compound represented by formula (3-7), a compound represented by formula (3-8), a compound represented by formula (3-9), a compound represented by formula (3-10), and a compound represented by formula (3-11); and
optionally, a first compound represented by formula (1):

wherein:
R 1 is a group having a cyclic structure;
X 11 and X 12 are each independently a hydrogen atom, a fluorine atom, or a fluorinated hydrocarbon group, provided that at least one of X 11 and X 12 is not a hydrogen atom;
A 11 and A 12 are each independently a hydrogen atom, or a hydrocarbon group having a carbon number of 1 to 20;
m 1 is an integer of 0 to 5;
n 1 is an integer of 1 to 4;
G is a single bond, or a divalent linking group; and
Z 1 + , Z 2 + and Z 3 + are each independently a monovalent onium cation,

wherein
an amount of the radiation-sensitive acid generator is from 7 to 35 mass parts with respect to 100 mass parts of the base resin,
an amount of the acid diffusion controlling agent is from 5 to 110 mass parts with respect to 100 mass parts of the radiation-sensitive acid generator, and
an amount of the fluorine-containing resin is from 1 to 5 mass parts with respect to 100 mass parts of the base resin.

2. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator comprises the first compound, and a total content of the first compound is not less than 1 part by mass and not more than 45 parts by mass based on 100 parts by mass of the base resin.

3. The radiation-sensitive resin composition according to claim 1 , wherein a molecular weight of an anionic moiety in the radiation-sensitive acid generator is 230 or more.

4. A method of forming a resist pattern, comprising:
forming a resist film from the radiation-sensitive resin composition according to claim 1 ;
exposing the resist film; and
developing the exposed resist film.

5. The radiation-sensitive resin composition according to claim 1 , wherein the acid diffusion controlling agent is an onium salt compound wherein the onium salt compound is degraded and loses acid diffusion controlling properties by an exposure.

6. The radiation-sensitive resin composition according to claim 5 , wherein the onium salt compound is triphenylsulfonium salicylate or triphenylsulfonium 10-camphorsulfonate.

7. The radiation-sensitive resin composition according to claim 1 ,
wherein Z 1 + , Z 2 + , and Z 3 + are each independently represented by formula (X-1):

wherein:
k1, k2 and k3 are each independently an integer of 0 to 5; and
R a1 , R a2 and R a3 are each independently, at each occurrence, a substituted or unsubstituted, straight or branched chain alkyl group, alkoxy group or alkoxycarbonyloxy group having a carbon number of 1 to 12; a substituted or unsubstituted, monocyclic or polycyclic cycloalkyl group having a carbon number of 3 to 12; a substituted or unsubstituted aromatic hydrocarbon group having a carbon number of 6 to 12; a hydroxy group; —OSO 2 —R P ; —SO 2 —R Q ; or —S—R T , wherein R P , R Q and R T are each independently, at each occurrence, a substituted or unsubstituted, straight or branched chain alkyl group having a carbon number of 1 to 12; a substituted or unsubstituted alicyclic hydrocarbon group having a carbon number of 5 to 25; or a substituted or unsubstituted aromatic hydrocarbon group having a carbon number of 6 to 12.

8. The radiation-sensitive resin composition according to claim 1 , wherein the monovalent onium cation represented by Z 1 + , Z 2 + and Z 3 + is an unsubstituted triphenylsulfonium.

9. The method according to claim 4 , wherein the radiation-sensitive acid generator comprises the first compound, and a total content of the first compound is not less than 1 part by mass and not more than 45 parts by mass based on 100 parts by mass of the base resin.

10. The method according to claim 4 , wherein a molecular weight of an anionic moiety in the radiation-sensitive acid generator is 230 or more.

11. The method according to claim 4 , wherein the acid diffusion controlling agent is an onium salt compound wherein the onium salt compound is degraded and loses acid diffusion controlling properties by an exposure.

12. The method according to claim 11 , wherein the onium salt compound is triphenylsulfonium salicylate or triphenylsulfonium 10-camphorsulfonate.

13. The method according to claim 4 ,
wherein Z 1 + , Z 2 + , and Z 3 + are each independently represented by formula (X-1):

wherein:
k1, k2 and k3 are each independently an integer of 0 to 5; and
R a1 , R a2 and R a3 are each independently, at each occurrence, a substituted or unsubstituted, straight or branched chain alkyl group, alkoxy group or alkoxycarbonyloxy group having a carbon number of 1 to 12; a substituted or unsubstituted, monocyclic or polycy

Assignees

• Jsr Corp

Inventors

• Maruyama Ken

Classifications

• G03F7/0045 Primary

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

• C07C303/32

  of salts of sulfonic acids · CPC title

• C07C309/06

  containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton · CPC title

• C07C309/12

  containing esterified hydroxy groups bound to the carbon skeleton · CPC title

• C07C309/19

  of a saturated carbon skeleton containing rings · CPC title