Radiation-sensitive resin composition, resist pattern-forming method, acid diffusion control agent, carboxylic acid salt and carboxylic acid
A radiation-sensitive resin composition contains: a polymer having an acid-labile group, a radiation-sensitive acid generator, a compound represented by the following formula (1), and a solvent. In the formula (1), X represents an oxygen atom or a sulfur atom; R 1 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 to R 5 each independently represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally two or more of R 2 to R 5 taken together represent an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which the two or more of R 2 to R 5 bond; Z n+ represents a cation having a valency of n; and n is an integer of 1 to 3.
1. A radiation-sensitive resin composition, comprising:
a solvent;
a polymer comprising an acid-labile group;
a radiation-sensitive acid generator; and
a compound of formula (1),
wherein X is an oxygen atom or a sulfur atom; R 1 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 and R 3 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group-substituted hydrocarbon group, a hydroxy group- and a fluorine atom-substituted hydrocarbon group, or a group comprising an aliphatic heterocyclic structure, or R 2 and R 3 taken together an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond: R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally R 4 and R 5 taken together are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 4 and R 5 bond; Z n+ represents a cation having a valency of n; and n is an integer of 1 to 3.
2. The radiation-sensitive resin composition according to claim 1 , wherein R 1 in the formula (1) is the hydrogen atom.
3. The radiation-sensitive resin composition according to claim 2 , wherein R 2 and R 3 in the formula (1) taken together are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond.
4. The radiation-sensitive resin composition according to claim 2 , wherein R 2 and R 3 in the formula (1) each independently are the group comprising an aliphatic heterocyclic structure, the hydrogen atom, the hydrocarbon group, the hydroxy group-substituted hydrocarbon group, or the hydroxy group- and fluorine atom-substituted hydrocarbon group.
5. The radiation-sensitive resin composition according to claim 2 , wherein R 4 and R 5 in the formula (1) each independently is a hydrogen atom.
6. The radiation-sensitive resin composition according to claim 1 , wherein R 2 and R 3 in the formula (1) taken together are the alicyclic structure having 3 to 20 ring atoms or the aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond.
7. The radiation-sensitive resin composition according to claim 6 , wherein R 4 and R 5 in the formula (1) each independently is a hydrogen atom.
8. The radiation-sensitive resin composition according to claim 1 , wherein R 2 and R 3 in the formula (1) are each independently the group comprising an aliphatic heterocyclic structure, the hydrogen atom, the hydrocarbon group, the hydroxy group-substituted hydrocarbon group, or the hydroxy group- and fluorine atom-substituted hydrocarbon group.
9. The radiation-sensitive resin composition according to claim 8 , wherein R 4 and R 5 in the formula (1) each independently is a hydrogen atom.
10. The radiation-sensitive resin composition according to claim 1 , wherein R 4 and R 5 in the formula (1) is each independently the hydrogen atom.
11. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator generates sulfonic acid upon irradiation with a radioactive ray.
12. A resist pattern-forming method comprising:
applying the radiation-sensitive resin composition of claim 1 directly or indirectly on one face of a substrate to obtain a resist film;
exposing the resist film; and
developing the resist film exposed.
13. An acid diffusion control agent of formula (1′),
wherein X is an oxygen atom or a sulfur atom; R 1 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 and R 3 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group-substituted hydrocarbon group, a hydroxy group- and a fluorine atom-substituted hydrocarbon group, or a group comprising an aliphatic heterocyclic structure, or R 2 and R 3 taken together an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond; R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally R 4 and R 5 taken together are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 4 and R 5 bond; Z n+ is a radiation-sensitive cation having a valency of n; and n is an integer of 1 to 3.
14. A carboxylic acid salt of formula (i),
wherein X is an oxygen atom or a sulfur atom; R 1 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 and R 3 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group-substituted hydrocarbon group, a hydroxy group- and a fluorine atom-substituted hydrocarbon group, or a group comprising an aliphatic heterocyclic structure, or R 2 and R 3 taken together an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond: R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally R 4 and R 5 taken together represent are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 4 and R 5 bond; Z n+ is a radiation-sensitive cation having a valency of n; and n is an integer of 1 to 3.
15. The carboxylic acid salt according to claim 14 , wherein R 2 and R 3 in the formula (i) are each independently the group comprising an aliphatic heterocyclic structure, the hydrogen atom, the hydrocarbon group, the hydroxy group-substituted hydrocarbon group, or the hydroxy group- and fluorine atom-substituted hydrocarbon group.
16. The carboxylic acid salt according to claim 14 , wherein Z n+ in the formula (i) is an onium cation.
17. The carboxylic acid salt according to claim 16 , wherein the onium cation is a sulfonium cation, an iodonium cation, a tetrahydrothiophenium cation or a combination thereof.
18. The carboxylic acid salt according to claim 16 , wherein n in the formula (i) is 2 or 3.
19. The carboxylic acid salt according to claim 14 , wherein
n in the formula (i) is 1, and
Z n+ is an alkali metal cation.
20. A carboxylic acid of formula (i′),
wherein X is an oxygen atom or a sulfur atom; R 1 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 and R 3 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group-substituted hydrocarbon group, a hydroxy group- and a fluorine atom-substituted hydrocarbon group, or a group comprising an aliphatic heterocyclic structure, or R 2 and R 3 taken together an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond; and R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally R 4 and R 5 taken together are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 4 and R 5 bond.