Radiation-sensitive resin composition, resist pattern-forming method, acid generator and compound

Patent metadata

Field	Value
Publication number	US-9523911-B2
Application number	US-201414282270-A
Country	US
Kind code	B2
Filing date	May 20, 2014
Priority date	May 20, 2013
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

The present invention provides a radiation-sensitive resin composition that contains a polymer having a structural unit that includes an acid-labile group; and an acid generator, wherein the acid generator includes a compound including a sulfonate anion having SO 3 − , wherein a hydrogen atom or an electron-donating group bonds to an α carbon atom with respect to SO 3 − , and an electron-withdrawing group bonds to a β carbon atom with respect to SO 3 − ; and a radiation-degradable onium cation. The compound preferably has a group represented by the following formula (1-1) or (1-2). In the following formulae (1-1) and (1-2), R 1 and R 2 each independently represent a hydrogen atom or a monovalent electron-donating group. R 3 represent a monovalent electron-withdrawing group. R 4 represents a hydrogen atom or a monovalent hydrocarbon group.

First claim

What is claimed is:

1. A radiation-sensitive resin composition, comprising:
a polymer comprising a structural unit which comprises an acid-labile group; and
at least one acid generator comprising a first acid generator represented by formula (2), and optionally a second acid generator other than the first acid generator:

wherein in the formula (2):
Z represents a group represented by formula (1-1) or (1-2);
X represents OCO—;
n is an integer of 1;
R 5 represents a cycloalkyl group, or a group comprising a lactone structure;

wherein in the formulae (1-1) and (1-2):
R 1 and R 2 each independently represent a hydrogen atom or a methyl group;
R 3 represents a cyano group;
R 4 represents a hydrogen atom; and
M + represents a monovalent radiation-degradable onium cation.

2. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-degradable onium cation is a sulfonium cation or an iodonium cation.

3. The radiation-sensitive resin composition according to claim 1 , wherein the structural unit that includes an acid-labile group is represented by formula (4):

wherein in the formula (4),
R 7 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group;
R 8 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms;
R 9 and R 10 each independently represent a monovalent linear hydrocarbon group having 1 to 10 carbon atoms or a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms; and
R 9 and R 10 optionally taken together represent an alicyclic structure having 3 to 20 carbon atoms together with the carbon atom to which R 9 and R 10 bond.

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

5. The radiation-sensitive resin composition according to claim 1 , wherein a content of the first acid generator in the at least one acid generator is in a range of 25% by mass to 90% by mass.

6. The radiation-sensitive resin composition according to claim 1 , wherein a content of the first acid generator in the at least one acid generator is in a range of 30% by mass to 70% by mass.

7. The radiation-sensitive resin composition according to claim 1 , further comprising an acid diffusion controller.

8. The radiation-sensitive resin composition according to claim 1 , further comprising a fluorine atom-containing polymer other than the polymer.

9. The radiation-sensitive resin composition according to claim 1 , wherein Z represents a group represented by formula (1-1).

10. The radiation-sensitive resin composition according to claim 9 , wherein R 1 and R 2 each represent a hydrogen atom.

11. A compound represented by formula (2):

wherein in the formula (2):
Z represents a group represented by formula (1-1) or (1-2);
X represents OCO—;
n is an integer of 1;
R 5 represents a cycloalkyl group, or a group comprising a lactone structure;

wherein in the formulae (1-1) and (1-2):
R 1 and R 2 each independently represent a hydrogen atom or a methyl group;
R 3 represents a cyano group;
R 4 represents a hydrogen atom; and
M + represents a monovalent radiation-degradable onium cation.

12. The compound according to claim 11 , wherein Z represents a group represented by formula (1-1).

13. The compound according to claim 12 , wherein R 1 and R 2 each represent a hydrogen atom.

Assignees

• Jsr Corp

Inventors

• Tomioka Hiroshi
• Kimoto Takakazu
• Asano Yusuke

Classifications

• C07C381/12

  Sulfonium compounds · CPC title

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title

• G03F7/0397

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

• C07C25/18

  Polycyclic aromatic halogenated hydrocarbons · CPC title

• G03F7/0045 Primary

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