Photoresist composition, compound, and production method thereof

Patent metadata

Field	Value
Publication number	US-9477149-B2
Application number	US-201414491286-A
Country	US
Kind code	B2
Filing date	Sep 19, 2014
Priority date	Mar 19, 2012
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

Abstract

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.

First claim

The invention claimed is:

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.

Assignees

• Jsr Corp

Inventors

• Namai Hayato
• Ikeda Norihiko
• Kawakami Takanori

Classifications

• C07D311/74

  Benzo[b]pyrans, hydrogenated in the carbocyclic ring · CPC title

• C07D319/06

  not condensed with other rings · CPC title

• C07D493/10

  Spiro-condensed systems · CPC title

• C07D211/46

  having a hydrogen atom as the second substituent in position 4 · CPC title

• C07C2601/10

  the ring being unsaturated · CPC title