IP Library Granted Patent US 8,470,513
Granted Patent B2
US 8,470,513 · App. 13/242,920 · Granted Jun 25, 2013

Radiation-sensitive resin composition and polymer

Inventors: Kota Nishino (Tokyo, JP); Ken Maruyama (Tokyo, JP); Daisuke Shimizu (Tokyo, JP); Toshiyuki Kai (Tokyo, JP)
Assignee: JSR Corporation
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Quick Facts
Patent No.
US 8,470,513
App. No.
13/242,920
Granted
Jun 25, 2013
Kind
B2
Abstract

A radiation-sensitive resin composition includes a polymer that includes at least one repeating unit (i) selected from a repeating unit shown by a formula (1), (2), and (3); and a repeating unit (ii) shown by a formula (4). R 1 represents a hydrogen atom or a methyl group. Each R 2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms. p is an integer from 0 to 3, and q is an integer from 1 to 3, and p+q≦5. A chemically-amplified positive-tone resist film that is sensitive to extreme ultraviolet rays (EUV) can be formed using the radiation-sensitive resin composition.

Claims (25)

1. A radiation-sensitive resin composition comprising:

a solvent; and

a polymer comprising:

a repeating unit (i) shown by a formula (1);

a repeating unit (ii) shown by a formula (4); and

at least one repeating unit (iii) selected from a repeating unit shown by a formula (5) and a repeating unit shown by a formula (6), a content of the repeating unit (iii) in the polymer being 20 mol % or more based on a total amount of repeating units included in the polymer,

wherein p is an integer from 0 to 3, q is an integer from 1 to 3, a sum of p and q is equal to or less than 5, R 1 represents a hydrogen atom or a methyl group, each R 2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms, and each R 2 is a same as or different from each other when p is 2 or 3,

wherein R 3 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, each R f independently represents one of a fluorine atom and a linear or branched perfluoroalkyl group having 1 to 10 carbon atoms, each R f is a same as or different from each other, A represents an ester bond or a single bond, G represents an alkylene group having 1 to 5 carbon atoms or a divalent alicyclic hydrocarbon group having 6 to 10 carbon atoms, M + represents a metal ion or a monovalent onium cation, and n is an integer from 1 to 8,

wherein r is an integer equal to or larger than 0, s is an integer equal to or larger than 1, a sum of r and s is equal to or less than 5, each of R 6 to R 11 represents a hydrogen atom or a fluorine atom and at least one of R 6 to R 11 represents a fluorine atom, R 12 represents a hydrogen atom or a linear or branched alkyl group having 1 to 12 carbon atoms, R 4 represents a hydrogen atom or a methyl group, each R 5 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms, each R 5 is a same as or different from each other when r is 2 or more, R 13 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, and B represents a linear, branched, or cyclic divalent hydrocarbon group having 1 to 40 carbon atoms.

2. The radiation-sensitive resin composition according to claim 1 , wherein the repeating unit (ii) is shown by a formula (4-1) or (4-2),

wherein R 3′ represents a hydrogen atom or a methyl group.

3. The radiation-sensitive resin composition according to claim 1 , the polymer further comprising an acid-dissociable group-containing repeating unit shown by a formula (7),

wherein R 14 represents a hydrogen atom, a methyl group, or a trifluoromethyl group, and X represents an acid-dissociable group including an alicyclic skeleton having 3 to 25 carbon atoms.

4. The radiation-sensitive resin composition according to claim 1 , wherein a content of the repeating unit (i) in the polymer being 10 mol % or more based on a total amount of repeating units included in the polymer.

5. A polymer comprising:

a repeating unit (i) shown by a formula (1);

a repeating unit (ii) shown by a formula (4);

at least one repeating unit (iii) selected from a repeating unit shown by a formula (5) and a repeating unit shown by a formula (6), a content of the repeating unit (iii) in the polymer being 20 mol % or more based on a total amount of repeating units included in the polymer; and

an acid-dissociable group-containing repeating unit shown by a formula (7),

the polymer having a polystyrene-reduced weight average molecular weight determined by gel permeation chromatography of 3000 to 100,000,

wherein p is an integer from 0 to 3, q is an integer from 1 to 3, a sum of p and q is equal to or less than 5, R 1 represents a hydrogen atom or a methyl group, each R 2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms, and each R 2 is a same as or different from each other when p is 2 or 3,

wherein R 3 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, each R f independently represents one of a fluorine atom and a linear or branched perfluoroalkyl group having 1 to 10 carbon atoms, each R f is a same as or different from each other, A represents an ester bond or a single bond, G represents an alkylene group having 1 to 5 carbon atoms or a divalent alicyclic hydrocarbon group having 6 to 10 carbon atoms, M + represents a metal ion or a monovalent onium cation, and n is an integer from 1 to 8,

wherein r is an integer equal to or larger than 0, s is an integer equal to or larger than 1, a sum of r and s is equal to or less than 5, each of R 6 to R 11 represents a hydrogen atom or a fluorine atom and at least one of R 6 to R 11 represents a fluorine atom, R 12 represents a hydrogen atom or a linear or branched alkyl group having 1 to 12 carbon atoms, R 4 represents a hydrogen atom or a methyl group, each R 5 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms, each R 5 is a same as or different from each other when r is 2 or more, R 13 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, and B represents a linear, branched, or cyclic divalent hydrocarbon group having 1 to 40 carbon atoms,

wherein R 14 represents a hydrogen atom, a methyl group, or a trifluoromethyl group, and X represents an acid-dissociable group including an alicyclic skeleton having 3 to 25 carbon atoms.

6. The polymer according to claim 5 , wherein a content of the repeating unit (i) in the polymer being 10 mol % or more based on a total amount of repeating units included in the polymer.

Assignments (3)
MERGER Recorded Mar 23, 2026
From: JSR CORPORATION
To: JICC-02, CO., LTD
Reel/Frame 075191/0149 →
CHANGE OF NAME Recorded Mar 23, 2026
From: JICC-02 CO., LTD
To: JSR CORPORATION
Reel/Frame 075192/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2011
From: NISHINO, KOTA; MARUYAMA, KEN; SHIMIZU, DAISUKE; KAI, TOSHIYUKI
To: JSR CORPORATION
Reel/Frame 027232/0096 →
Priority Claims (1)
JP 2009-080223 · Mar 27, 2009 · national
Continuity (2)
Continuation PCTJP2010054922 · Mar 23, 2010
Related Publication 20120058429A1 · Mar 8, 2012