Radiation-sensitive resin composition, polymer and compound

Patent metadata

Field	Value
Publication number	US-9459532-B2
Application number	US-201313853254-A
Country	US
Kind code	B2
Filing date	Mar 29, 2013
Priority date	Sep 30, 2010
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

A radiation-sensitive resin composition includes a polymer, an acid generating agent, and an organic solvent. The polymer includes a first structural unit derived from a compound represented by a formula (1), and a second structural unit derived from a compound represented by a formula (2). R 1 represents an organic group having a valency of (a+2) that represents a ring structure having 3 to 8 carbon atoms together with the carbon atom constituting a lactone ring. R 2 represents a fluorine atom, a hydroxyl group, an organic group having 1 to 20 carbon atoms or the like.

First claim

The invention claimed is:

1. A radiation-sensitive resin composition comprising:
a first polymer comprising a first structural unit derived from a compound represented by formula (1) or formula (1-47), and a second structural unit derived from a compound represented by formula (2);
an acid generating agent; and
an organic solvent,

wherein, in the formula (1),
R 1 represents an organic group having a valency of (a+2) that represents a ring structure having 3 to 8 carbon atoms together with the carbon atom constituting the lactone ring;
R 2 represents a fluorine atom, a hydroxyl group, a chain hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a methoxy carbonyl group, an ethoxy carbonyl group, an oxacycloalkyloxy group having 2 to 10 carbon atoms, or —R′—X—R″, a part or all of hydrogen atoms of the chain hydrocarbon group having 1 to 20 carbon atoms optionally being substituted with a halogen atom, a cyano group, a carboxyl group, a hydroxyl group or a thiol group,
wherein R′ represents a single bond or a hydrocarbon group having 1 to 10 carbon atoms, R″ represents an alkylsilyl group having 1 to 20 carbon atoms, and X represents —O— or —NH—, and
wherein at least one group of R 1 and R 2 has a hetero atom or a halogen atom;

a is an integer of 1 to 6,
wherein in a case where a is 2 or greater, each R 2 is identical or different, and at least two R e s optionally taken together represent a ring structure;

R 3 represents a hydrogen atom or a methyl group;
R 4 represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 6 carbon atoms; and
R 5 represents a hydrogen atom, or R 5 and R 4 taken together represent a cycloalkanediyl group having 3 to 8 carbon atoms together with the carbon atom to which R 5 and R 4 bond, and
in the formula (2),
R 6 represents a hydrogen atom or a methyl group;
R 7 , R 8 and R 9 each independently represent an alkyl group having 1 to 6 carbon atoms, or R 7 and R 8 taken together represent a ring structure together with the carbon atom to which R 7 and R 8 bond and R 9 represents an alkyl group having 1 to 6 carbon atoms, wherein a hydrogen atom of the alkyl group represented by R 7 , R 8 or R 9 is not substituted or substituted.

2. The radiation-sensitive resin composition according to claim 1 , wherein at least one group of R 1 and R 2 in the formula (1) comprises an oxygen atom.

3. The radiation-sensitive resin composition according to claim 1 , wherein R 1 in the formula (1) represents a chain hydrocarbon group having a valency of (a+2) that includes one or more of —CO—, —COO—, —OCO—, —O—, —NR—, —S—, —SO—, and —SO 2 in a skeleton chain, wherein R represents a hydrogen atom or an organic group having 1 to 20 carbon atoms.

4. The radiation-sensitive resin composition according to claim 1 , wherein “a” in the formula (1) is 1.

5. The radiation-sensitive resin composition according to claim 1 , wherein the compound represented by the formula (2) is represented by formula (2a) or formula (2b):

wherein, in the formula (2a) and the formula (2b), R 6 and R 9 are as defined in the formula (2), and b is an integer of 1 to 5.

6. The radiation-sensitive resin composition according to claim 1 , wherein R 2 in the formula (1) represents a fluorine atom, a hydroxyl group, a chain hydrocarbon group having 1 to 5 carbon atoms, a methoxy carbonyl group, an ethoxy carbonyl group, or an oxacycloalkyloxy group having 2 to 10 carbon atoms, and wherein in a case where a is 2 or greater, each R 2 is identical or different, and at least two R 2 s optionally taken together represent a ring structure.

7. The radiation-sensitive resin composition according to claim 1 , wherein a content of the first structural unit in the first polymer with respect to entire structural units constituting the first polymer is no less than 5 mol % and no greater than 70 mol %.

8. The radiation-sensitive resin composition according to claim 1 , wherein a content of the first structural unit in the first polymer with respect to entire structural units constituting the first polymer is no less than 5 mol % and no greater than 50 mol %.

9. The radiation-sensitive resin composition according to claim 1 , wherein in the formula (1), the alkylsilyl group represented by R″ is a trimethylsilyl group or a tert-butyldimethylsilyl group.

10. The radiation-sensitive resin composition according to claim 1 , further comprising a fluorine-containing polymer comprising a fluorine atom.

11. The radiation-sensitive resin composition according to claim 10 , wherein an amount of the fluorine-containing polymer in the radiation-sensitive resin composition is 0.1 parts by mass to 20 parts by mass with respect to 100 parts by mass of the first polymer.

12. The radiation-sensitive resin composition according to claim 10 , wherein an amount of the fluorine-containing polymer in the radiation-sensitive resin composition is 1 part by mass to 10 parts by mass with respect to 100 parts by mass of the first polymer.

13. The radiation-sensitive resin composition according to claim 10 , wherein an amount of the fluorine-containing polymer in the radiation-sensitive resin composition is 1 part by mass to 7.5 parts by mass with respect to 100 parts by mass of the first polymer.

14. The radiation-sensitive resin composition according to claim 10 , wherein a proportion of the fluorine atom in the fluorine-containing polymer is greater than a proportion of a fluorine atom in the first polymer.

15. The radiation-sensitive resin composition according to claim 10 , wherein a proportion of the fluorine atom in the fluorine-containing polymer is from 5% by mass to 50% by mass.

16. The radiation-sensitive resin composition according to claim 10 , wherein a proportion of the fluorine atom in the fluorine-containing polymer is from 5% by mass to 45% by mass.

17. The radiation-sensitive resin composition according to claim 1 , further comprising an acid diffusion control agent.

18. The radiation-sensitive resin composition according to claim 17 , an amount of the acid diffusion control agent in the radiation-sensitive resin composition is from 0.1 parts by mass to 8 parts by mass with respect to 100 parts by mass of the first polymer.

19. The radiation-sensitive resin composition according to claim 1 , wherein R 1 represents a monocyclic alicyclic structure together with the carbon atom constituting the lactone ring.

Assignees

• Jsr Corp

Inventors

• Ikeda Norihiko
• Nakamura Shin-Ichi

Classifications

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• G03F7/0397 Primary

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

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• C08L2312/06

  by radiation · CPC title

• C09D133/04

  Homopolymers or copolymers of esters {(C09D143/04 takes precedence)} · CPC title