Photoresist composition, compound, and production method thereof

Patent metadata

Field	Value
Publication number	US-9720322-B2
Application number	US-201615252553-A
Country	US
Kind code	B2
Filing date	Aug 31, 2016
Priority date	Mar 19, 2012
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

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 includes an acid-labile group; and
a first compound represented by formula (1):

wherein, in the formula (1), R 1 and R 2 each independently represent a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and 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; X represents 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; A − represents —SO 3 − or —CO 2 − ; and M + represents a monovalent onium cation, wherein in a case where A − represents —CO 2 − , at least one of R 1 , R 2 , R 3 and R does not represent a hydrogen atom.

2. The photoresist composition according to claim 1 , wherein the first compound represented by the formula (1) is any one of compounds represented by formulae (1-1-1) to (1-1-5), or a mixture of these compounds:

wherein, in the formulae (1-1-1) to (1-1-5), M + , A − , R 1 , R 2 , R 3 and R are as defined in the formula (1); and R p1 , R p2 , R p3 and R p4 each independently represent a divalent organic group.

3. The photoresist composition according to claim 1 , wherein the first compound represented by the formula (1) is any one of compounds represented by formulae (1-2-1), (1-2-2), or (1-2-4), or a mixture of these compounds:

wherein, in the formulae (1-2-1), (1-2-2), and (1-2-4), M + , A − , R 1 , R 2 , R 3 , R and R a are as defined in the formula (1); and R p1 and R p2 each independently represent a divalent organic group.

4. The photoresist composition according to claim 1 , comprising an acid diffusion control agent, which comprises the first compound.

5. The photoresist composition according to claim 4 , 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.

6. The photoresist composition according to claim 4 , further comprising an acid generating agent, which differs from the first compound.

7. The photoresist composition according to claim 1 comprising an acid generating agent, which comprises the first compound.

8. The photoresist composition according to claim 7 , further comprising an acid diffusion control agent, which differs from the first compound.

9. The photoresist composition according to claim 1 , wherein R represents a substituted or unsubstituted monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms or a substituted or unsubstituted 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 hydroxy group or a halogen atom.

11. A compound represented by formula (1):

wherein, in the formula (1), R 1 and R 2 each independently represent a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 20 carbon atoms, R 3 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R represents 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; X represents an oxygen atom or wherein R a represents a hydroxy group or a monovalent organic group having 1 to 20 carbon atoms; A − represents —SO 3 − or —CO 2 − ; and 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.

12. The compound according to claim 11 , wherein in the formula (1), X represents an oxygen atom, and R is an acid-nonlabile group represented by formula (i):

wherein, in the formula (i), R b1 , R b2 and R b3 each independently represent a hydrogen atom, a hydroxy group or a monovalent organic group having 1 to 19 carbon atom, wherein at least one of the monovalent organic group comprises at least one of a polar group and a linking group, and the linking group is —O—CO—O—, —S—, —O—, —SO 2 —O—, —NH— or —CO—O—, and wherein two or more of R b1 , R b2 and R b3 optionally taken together represent a ring structure by binding with each other, and at least one of R b1 , R b2 and R b3 does not represent a hydrogen atom.

13. The compound according to claim 11 , wherein in the formula (1), X represents an oxygen atom, and R is an acid-labile group represented by formula (ii):

wherein, in the formula (ii), R c1 , R c2 and R c3 each independently represent an alkyl group having 1 to 19 carbon atoms or a monovalent alicyclic hydrocarbon group having 3 to 19 carbon atoms, wherein a part or all of hydrogen atoms included in the alkyl group and the alicyclic hydrocarbon group are unsubstituted or substituted, and wherein two of R c1 , R c2 and R c3 optionally taken together represent a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms by binding with each other together with the carbon atom to which the two of R c1 , R c2 and R c3 bond.

14. The compound according to claim 11 , wherein R represents a substituted or unsubstituted monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms or a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.

Assignees

• Jsr Corp

Inventors

• Namai Hayato
• Ikeda Norihiko
• Kawakami Takanori

Classifications

• C07D237/16

  Two oxygen atoms · CPC title

• C07D311/74

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

• C07C2601/18

  with a ring being at least seven-membered · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• C07D313/06

  condensed with carbocyclic rings or ring systems · CPC title