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

Patent metadata

Field	Value
Publication number	US-2017038679-A1
Application number	US-201615332203-A
Country	US
Kind code	A1
Filing date	Oct 24, 2016
Priority date	May 20, 2013
Publication date	Feb 9, 2017
Grant date	—

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

1 - 12 . (canceled)

13 : 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:
(R 5  n X—Z  (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 to 3;
R 5 represents a cycloalkyl group, or a group comprising a lactone structure;
in a case where n is no less than 2, a plurality of R 5 s are identical or different; and
two or more of Z, X and R 5 optionally bond to each other to form a ring 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 trifluoromethyl group;
R 4 represents a hydrogen atom; and
M + represents a monovalent radiation-degradable onium cation.

14 : The radiation-sensitive resin composition according to claim 13 ,
wherein n in the formula (2) is 1.

15 : The radiation-sensitive resin composition according to claim 13 , wherein the radiation-degradable onium cation is a sulfonium cation or an iodonium cation.

16 : The radiation-sensitive resin composition according to claim 13 , 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.

17 : The radiation-sensitive resin composition according to claim 13 , 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.

18 : The radiation-sensitive resin composition according to claim 13 , 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.

19 : The radiation-sensitive resin composition according to claim 13 , further comprising an acid diffusion controller.

20 : The radiation-sensitive resin composition according to claim 13 , further comprising a fluorine atom-containing polymer other than the polymer.

21 : The radiation-sensitive resin composition according to claim 13 , wherein Z represents a group represented by formula (1-1).

22 : The radiation-sensitive resin composition according to claim 21 , wherein n is 1.

23 : The radiation-sensitive resin composition according to claim 22 , wherein R 1 and R 2 each represent a hydrogen atom.

24 : A resist pattern-forming method, comprising:
applying the radiation-sensitive resin composition according to claim 13 on a substrate to form the resist film; exposing the resist film; and developing the exposed resist film.

25 : A compound represented by formula (2):
(R 5  n X—Z  (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 to 3;
R 5 represents a cycloalkyl group, or a group comprising a lactone structure;
in a case where n is no less than 2, a plurality of R 5 s are identical or different; and
two or more of Z, X and R 5 optionally bond to each other to form a ring 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 trifluoromethyl group;
R 4 represents a hydrogen atom; and
M + represents a monovalent radiation-degradable onium cation.

26 : The compound according to claim 25 , wherein Z represents a group represented by formula (1-1).

27 : The compound according to claim 26 , wherein n is 1.

28 : The compound according to claim 27 , wherein R 1 and R 2 each represent a hydrogen atom.

Assignees

• Jsr Corp

Inventors

• Tomioka Hiroshi
• Kimoto Takakazu
• Asano Yusuke

Classifications

• C07C309/39

  containing halogen atoms bound to the carbon skeleton · CPC title

• G03F7/0397

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

• G03F7/2006

  using coherent light; using polarised light · CPC title

• C07C309/13

  containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton · CPC title

• G03F7/2041

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