Photoresist composition, compound, and production method thereof
A photoresist composition containing (A) a polymer having a structural unit (I) that includes an acid-labile group, and (I) a compound represented by the following formula (1). In the following formula (1), R 1 , R 2 , R 3 and R represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. X represents a single bond, an oxygen atom or —NR a —. R a represents a hydrogen atom, a hydroxy group or a monovalent organic group having 1 to 20 carbon atoms, and optionally taken together represents a ring structure by binding with R each other. A − represents —SO 3 − or —CO 2 − . M + represents a monovalent onium cation.
1. A photoresist composition comprising:
a polymer comprising a first structural unit that comprises an acid-labile group; and
a first compound represented by formula (2):
wherein, in the formula (2) represents a hydrogen atom, a hydroxy group or a monovalent organic group having 1 to 20 carbon atoms; A − represents —SO 3 − or —CO 2 − ; M + represents a monovalent onium cation; and n is an interger of 0 to 5.
2. The photoresist composition according to claim 1 , comprising an acid diffusion control agent, which comprises the first compound.
3. The photoresist composition according to claim 2 , wherein the acid-labile group in the first structural unit is polar, or the polymer further comprises a second structural unit represented by formula (3):
wherein, in the formula (3), R 4 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; L represents a single bond, —CO—O— or —CO—NH—; and R 5 represents an acid-nonlabile group comprising a polar group.
4. The photoresist composition according to claim 2 , further comprising an acid generating agent, which differs from the first compound.
5. The photoresist composition according to claim 1 , comprising an acid generating agent, which comprises the first compound.
6. The photoresist composition according to claim 5 , further comprising an acid diffusion control agent, which differs from the first compound.
7. The photoresist composition according to claim 1 , wherein R a represents a monovalent alkyl group having 1 to 20 carbon atoms.
8. The photoresist composition according to claim 1 , wherein R a represents a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms.
9. The photoresist composition according to claim 1 , wherein R a represents a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.
10. The photoresist composition according to claim 1 , wherein M + represents a sulfonium cation represented by formula (M′) or an iodonium cation represented by formula (M″):
wherein R d1 to R d5 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a hydroxyl group or halogen atom.
11. A compound represented by a formula (2):
wherein, in the formula (2) represents a hydrogen atom, a hydroxy group or a monovalent organic group having 1 to 20 carbon atoms; A − represents —SO 3 − or —CO 2 − ; M + represents a monovalent onium cation; and n is an interger of 0 to 5.
12. The compound according to claim 11 , which is for use as an acid diffusion control agent or an acid generating agent.
13. The compound according to claim 11 , wherein R a represents a monovalent alkyl group having 1 to 20 carbon atoms.
14. The compound according to claim 11 , wherein R a represents a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms.
15. The compound according to claim 11 , wherein R a represents a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.
16. The compound according to claim 11 , wherein M + represents a sulfonium cation represented by formula (M′) or an iodonium cation represented by formula (M″):
wherein R d1 to R d5 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group or a halogen atom.
17. A method for producing a compound represented by formula (6) comprising:
allowing a compound represented by formula (4) to react with NaHSO 3 ; and
allowing the resulting compound to react with a compound represented by formula (5):
wherein, in the formulae (4) and (6), R 1 , R 2 , R 3 and R each independently represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, wherein two of R 1 , R 2 , R 3 and R optionally taken together represent a ring structure by binding with each other; and X represents a single bond, an oxygen atom or —NR a —, wherein R a represents a hydrogen atom, a hydroxy group or a monovalent organic group having 1 to 20 carbon atoms, and optionally taken together represents a ring structure by binding with R each other: in the formulae (5) and (6), M + represents a monovalent onium cation: and in the formula (5), E − represents a monovalent anion.