IP Library Granted Patent US 9,170,488
Granted Patent B2
US 9,170,488 · App. 14/307,296 · Granted Oct 27, 2015

Resist pattern-forming method, and radiation-sensitive resin composition

Inventors: Hirokazu Sakakibara (Tokyo, JP); Taiichi Furukawa (Tokyo, JP); Reiko Kimura (Tokyo, JP); Masafumi Hori (Tokyo, JP)
Assignee: JSR CORPORATION
G03F7/004G03F7/038G03F7/0392G03F7/0397G03F7/2041G03F7/325G03F7/0045G03F7/0046
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Quick Facts
Patent No.
US 9,170,488
App. No.
14/307,296
Granted
Oct 27, 2015
Kind
B2
Abstract

A resist pattern-forming method includes coating a radiation-sensitive resin composition on a substrate to provide a resist film. The resist film is exposed. The exposed resist film is developed using a developer solution including no less than 80% by mass of an organic solvent. The radiation-sensitive resin composition includes a polymer, a radiation-sensitive acid generator, and an acid diffusion controller which includes a compound having an amide group. The polymer has a weight average molecular weight in terms of the polystyrene equivalent of greater than 6,000 and includes a first structural unit that includes an acid-labile group. The polymer includes less than 5 mol % or 0 mol % of a second structural unit that includes a hydroxyl group.

Claims (50)

1. A resist pattern-forming method comprising:

coating a radiation-sensitive resin composition on a substrate to provide a resist film;

exposing the resist film; and

developing the exposed resist film using a developer solution comprising no less than 80% by mass of an organic solvent,

wherein the radiation-sensitive resin composition comprises:

a first polymer which has a weight average molecular weight in terms of the polystyrene equivalent of greater than 6,000 and comprises:

a first structural unit that comprises an acid-labile group; and

less than 5 mol % or 0 mol % of a second structural unit that comprises

a hydroxyl group;

a second polymer which comprises:

a third structural unit which comprises a fluorine atom; and

a fourth structural unit comprising an acid-labile group which comprises an alicyclic hydrocarbon group;

a radiation-sensitive acid generator; and

an acid diffusion controller which comprises a compound comprising an amide group.

2. The resist pattern-forming method according to claim 1 , wherein the first structural unit comprises a plurality of kinds of structural units, and at least one of the plurality of kinds of structural units is a fifth structural unit represented by formula (1):

wherein, in the formula (1), R represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; and R p represents an acid-labile group represented by formula (i):

wherein, in the formula (i), R p1 to R p3 each independently represent an alkyl group having 1 to 4 carbon atoms or an alicyclic hydrocarbon group having 4 to 9 carbon atoms; or two of R P1 to R P3 taken together represent a divalent alicyclic hydrocarbon group having 4 to 9 carbon atoms together with the carbon atom to which the two of R P1 to R P3 bond, and R P1 to R P3 other than the two of R P1 to R P3 represents an alkyl group having 1 to 4 carbon atoms or an alicyclic hydrocarbon group having 4 to 9 carbon atoms; or R P1 to R P3 taken together represent a divalent alicyclic hydrocarbon group having 4 to 9 carbon atoms together with the carbon atom to which R P1 to R P3 bond.

3. The resist pattern-forming method according to claim 2 , wherein R p1 , R p2 and R p3 in the formula (i) each independently represent an alkyl group having 1 to 4 carbon atoms; or R p1 represents an alkyl group having 1 to 4 carbon atoms, and R p2 and R p3 taken together represent a divalent alicyclic hydrocarbon group having 4 to 9 carbon atoms together with the carbon atom to which R p2 and R p3 bond.

4. The resist pattern-forming method according to claim 2 , wherein the first structural unit included in the first polymer comprises no less than 60 mol % and no greater than 95 mol % of the fifth structural unit.

5. The resist pattern-forming method according to claim 1 , wherein the organic solvent is an alcohol solvent, an ether solvent, a ketone solvent, an amide solvent, an ester solvent, a hydrocarbon solvent or a combination thereof.

6. The resist pattern-forming method according to claim 1 , wherein the acid diffusion controller comprises N acetyl-1-adamantylamine, tris(2-hydroxyethyl) isocyanurate, 4-hydroxy-N-amyloxycarbonylpiperidine, or a combination thereof.

7. A radiation-sensitive resin composition comprising:

a first polymer which has a weight average molecular weight in terms of the polystyrene equivalent of greater than 6,000 and comprises:

a first structural unit that comprises an acid-labile group; and

less than 5 mol % or 0 mol % of a second structural unit that comprises a hydroxyl group;

a second polymer which comprises:

a third structural unit which comprises a fluorine atom; and

a fourth structural unit comprising an acid-labile group which comprises an alicyclic hydrocarbon group;

a radiation-sensitive acid generator; and

an acid diffusion controller which comprises a compound comprising an amide group,

the radiation-sensitive resin composition being for use in a resist pattern-forming method comprising:

using a developer solution comprising no less than 80% by mass of an organic solvent.

8. The radiation-sensitive resin composition according to claim 7 , wherein the acid diffusion controller comprises N-acetyl-1-adamantylamine, tris(2-hydroxyethyl) isocyanurate, 4-hydroxy-N-amyloxycarbonylpiperidine, or a combination thereof.

9. A resist pattern-forming method comprising:

coating a radiation-sensitive resin composition on a substrate to provide a resist film;

exposing the resist film; and

developing the exposed resist film using a developer solution comprising no less than 80% by mass of an organic solvent,

wherein the radiation-sensitive resin composition comprises:

a first polymer which has a weight average molecular weight in terms of the polystyrene equivalent of greater than 6,000 and comprises:

a first structural unit that comprises an acid-labile group which

comprises an alicyclic hydrocarbon group; and

less than 5 mol % or 0 mol % of a second structural unit that comprises

a hydroxyl group;

a second polymer which comprises:

a third structural unit which comprises a fluorine atom; and

a fourth structural unit comprising an acid-labile group which

comprises an alicyclic hydrocarbon group;

a radiation-sensitive acid generator; and

an acid diffusion controller which comprises a compound comprising an amide group.

10. The resist pattern-forming method according to claim 9 , wherein the acid diffusion controller comprises N-acetyl-1-adamantylamine, tris(2-hydroxyethyl) isocyanurate, 4-hydroxy-N-amyloxycarbonylpiperidine, or a combination thereof.

Assignments (2)
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 →
Priority Claims (2)
JP 2010-233027 · Oct 15, 2010 · national
JP 2011-066669 · Mar 24, 2011 · national
Continuity (3)
Continuation 13861416 · Apr 12, 2013
Continuation PCTJP2011070197 · Sep 5, 2011
Related Publication 20140295350A1 · Oct 2, 2014