IP Library Granted Patent US 12,422,753
Granted Patent B2
US 12,422,753 · App. 17/998,927 · Granted Sep 23, 2025

Copolymer, positive resist composition, and method of forming resist pattern

Inventor: Manabu Hoshino (Tokyo, JP)
Assignee: ZEON CORPORATION
G03F7/0397C08F212/12C08F220/68C08F2800/10
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Quick Facts
Patent No.
US 12,422,753
App. No.
17/998,927
Granted
Sep 23, 2025
Kind
B2
Abstract

A copolymer includes a monomer unit (A) represented by formula (I), shown below, and a monomer unit (B) represented by formula (II), shown below, and has a weight-average molecular weight of 230,000 or more. In the formulae, L is a single bond or a divalent linking group, Ar is an optionally substituted aromatic ring group, R 1 is an alkyl group, R 2 is hydrogen, an alkyl group, a halogen atom, a haloalkyl group, a hydroxy group, a carboxy group, or a halocarboxy group, p is an integer of not less than 0 and not more than 5, and in a case in which more than one R 2 is present, each R 2 may be the same or different.

Claims (19)

1. A copolymer comprising:

a monomer unit (A) represented by formula (I), shown below,

where, in formula (I), L is a single bond or a divalent linking group and Ar is an optionally substituted aromatic ring group; and

a monomer unit (B) represented by formula (II), shown below,

where, in formula (II), R 1 is an alkyl group, R 2 is hydrogen, an alkyl group, a halogen atom, a haloalkyl group, a hydroxy group, a carboxy group, or a halocarboxy group, p is an integer of not less than 0 and not more than 5, and in a case in which more than one R 2 is present, each R 2 may be the same or different, wherein

the copolymer has a weight-average molecular weight of 230,000 or more, and

a difference between weight-average molecular weight Mw 20 thereof upon exposure with an electron beam irradiation dose of 20 μC/cm 2 and weight-average molecular weight Mw 40 thereof upon exposure with an electron beam irradiation dose of 40 μC/cm 2 is 12,100 or more.

2. The copolymer according to claim 1 , having a weight-average molecular weight of 280,000 or more.

3. The copolymer according to claim 1 , wherein a proportion of components having a molecular weight of less than 50,000 is 20% or less.

4. The copolymer according to claim 1 , wherein a proportion of components having a molecular weight of less than 100,000 is 30% or less.

5. The copolymer according to claim 1 , wherein a proportion of components having a molecular weight of more than 500,000 is 10% or more.

6. The copolymer according to claim 1 , wherein L is a divalent linking group that includes an electron withdrawing group.

7. The copolymer according to claim 6 , wherein the electron withdrawing group is at least one selected from the group consisting of a fluorine atom, a fluoroalkyl group, a cyano group, and a nitro group.

8. A positive resist composition comprising: the copolymer according to claim 1 ; and a solvent.

9. A method of forming a resist pattern comprising:

a step (A) of forming a resist film using the positive resist composition according to claim 8 ;

a step (B) of exposing the resist film; and

a step (C) of developing the resist film that has been exposed using a developer.

10. The method of forming a resist pattern according to claim 9 , wherein the developer includes an alcohol.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2022
From: HOSHINO, MANABU
To: ZEON CORPORATION
Reel/Frame 061784/0933 →
Priority Claims (1)
JP 2020-107294 · Jun 22, 2020 · national
Continuity (1)
Related Publication 20230288805A1 · Sep 14, 2023
References Cited (13)
US 4983495A · Tsutsumi et al. · 1991 [cited by applicant]
US 20210214481A1 · Hoshino · 2021 [cited by applicant]
US 20230063003A1 · Hoshino · 2023 [cited by examiner]
JP 86449039A · 1989 [cited by applicant]
JP 2017119744A · 2017 [cited by applicant]
JP 2018154754A · 2018 [cited by examiner]
JP 2020086063A · 2020 [cited by applicant]
JP 2021081657A · 2021 [cited by examiner]
WO WO2017130873A1 · 2017 [cited by examiner]
WO WO2019077956A1 · 2019 [cited by examiner]
WO 2020066806A1 · 2020 [cited by applicant]
Aug. 17, 2021, International Search Report issued in the International Patent Application No. PCT/JP2021/022376. [cited by applicant]
Dec. 13, 2022, International Preliminary Report on Patentability issued in the International Patent Application No. PCT/JP2021/022376. [cited by applicant]