IP Library Granted Patent US 12,032,290
Granted Patent B2
US 12,032,290 · App. 17/344,967 · Granted Jul 9, 2024

Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, and method for manufacturing electronic device

Inventors: Daisuke Asakawa (Shizuoka, JP); Takashi Kawashima (Shizuoka, JP); Akiyoshi Goto (Shizuoka, JP); Michihiro Shirakawa (Shizuoka, JP); Kei Yamamoto (Shizuoka, JP)
Assignee: FUJIFILM Corporation
G03F7/0397G03F7/0045G03F7/2004G03F7/30G03F7/322G03F7/327G03F7/40
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Quick Facts
Patent No.
US 12,032,290
App. No.
17/344,967
Granted
Jul 9, 2024
Kind
B2
Abstract

According to the present invention, an actinic ray-sensitive or radiation-sensitive resin composition including a resin P having a repeating unit represented by General Formula (P1) and a compound that generates an acid having a pKa of −1.40 or more upon irradiation with actinic rays or radiation; and a resist film, a pattern forming method, and a method for manufacturing an electronic device, each using the composition, are provided. M p represents a single bond or a divalent linking group. L p represents a divalent linking group. X p represents O, S, or NR N1 . R N1 represents a hydrogen atom or a monovalent organic group. R p represents a monovalent organic group.

Claims (62)

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:

a resin P having a repeating unit represented by General Formula (P1); and

a photoacid generator Aw,

wherein the photoacid generator Aw is a compound that generates an acid having a pKa of −1.40 or more upon irradiation with actinic rays or radiation,

the acid having a pKa of −1.40 or more is a sulfonic acid represented by any of General Formulae (Aw-1), (Aw-2), and (I) to (V),

in General Formula (P1),

M p represents a single bond or a divalent linking group,

L p represents a divalent linking group,

X p represents O, S, or NR N1 , R N1 represents a hydrogen atom or a monovalent organic group, and

R p represents a monovalent organic group,

in General Formula (Aw-1), R 11W represents a hydrogen atom or a monovalent organic group, R 12W represents a monovalent organic group, and Rf 1W represents a fluorine atom or a monovalent organic group including a fluorine atom,

in General Formula (Aw-2), R 21W , R 22W , and R 23W each independently represent a hydrogen atom, a fluorine atom, or a monovalent organic group, R 24W represents a monovalent organic group, and Rf 2W represents a fluorine atom or a monovalent organic group including a fluorine atom,

in General Formula (I), R 11 and R 12 each independently represent a monovalent organic group, R 13 represents a hydrogen atom or a monovalent organic group, L 1 represents a group represented by —CO—O—, —CO—, —O—, —S—, —O—CO—, —S—CO—, or —CO—S—, and two selected from R 11 , R 12 and R 13 may be bonded to each other to form a ring,

in General Formula (II), R 21 and R 22 each independently represent a monovalent organic group, R 23 represents a hydrogen atom or a monovalent organic group, L 2 represents a group represented by —CO—, —O—, —S—, —O—CO—, —S—CO—, or —CO—S—, and two selected from R 21 , R 22 , and R 23 may be bonded to each other to form a ring,

in General Formula (III), R 31 and R 33 each independently represent a hydrogen atom or a monovalent organic group, and R 31 and R 33 may be bonded to each other to form a ring,

in General Formula (IV), R 41 and R 43 each independently represent a hydrogen atom or a monovalent organic group, and R 41 and R 43 may be bonded to each other to form a ring, and

in General Formula (V), R 51 , R 52 , and R 53 each independently represent a hydrogen atom or a monovalent organic group, and two selected from R 51 , R 52 , and R 53 may be bonded to each other to form a ring.

2. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein a group represented by L p -R p in General formula (P1) includes an acid-decomposable group.

3. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein a group represented by L p -R p in General formula (P1) includes a polar group, and

the polar group is at least one group selected from the group consisting of an ester group, a sulfonate group, a sulfonamide group, a carboxylic acid group, a sulfonic acid group, a carbonate group, a carbamate group, a hydroxy group, a sulfoxide group, a sulfonyl group, a ketone group, an imide group, an amide group, a sulfonimide group, a cyano group, a nitro group, and an ether group.

4. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein L p represents —CO—O—, —CO—, —NR L1 —, a divalent aromatic group, or a divalent linking group formed by combination thereof, provided that R L1 represents a hydrogen atom or a monovalent organic group.

5. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein M p represents a single bond or an alkylene group having 1 to 5 carbon atoms.

6. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein the repeating unit represented by General Formula (P1) is a repeating unit represented by General Formula (P2) or (P3),

in General Formula (P2),

M p1 represents a single bond or an alkylene group having 1 to 5 carbon atoms, and

R p represents a monovalent organic group,

in General Formula (P3),

M p1 represents a single bond or an alkylene group having 1 to 5 carbon atoms,

R p represents a monovalent organic group, and

R N1 represents a hydrogen atom or a monovalent organic group.

7. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 6 ,

wherein R p is represented by General Formula (RP-1) or (RP-2),

in General Formula (RP-1),

R p1 to R p3 each independently represent an alkyl group, a cycloalkyl group, or an aryl group,

any two of R p1 , R p2 , or R p3 may be bonded to each other to form a ring structure, and

*represents a bonding site to the oxygen atom to which R p is bonded,

in General Formula (RP-2),

R p4 and R p5 each independently represent a hydrogen atom, an alkyl group, or a cycloalkyl group,

R p6 represents an alkyl group or a cycloalkyl group,

any two of R p4 , R p5 , or R p6 may be bonded to each other to form a ring structure, and

*represents a bonding site to the oxygen atom to which R p is bonded.

8. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein the resin P further includes a repeating unit K1 having an acid-decomposable group, which is different from the repeating unit represented by General Formula (P1).

9. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein the resin P further includes a repeating unit K2 having a polar group, which is different from the repeating unit represented by General Formula (P1).

10. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising at least one of:

a basic compound (DA);

a basic compound (DB) having basicity that is reduced or lost upon irradiation with actinic rays or radiation;

a compound (DC) that generates an acid having a pKa of 1.00 or more higher than the acid generated from the photoacid generator Aw;

a compound (DD) having a nitrogen atom and having a group that is eliminated by an action of an acid; or

an onium salt compound (DE) having a nitrogen atom in a cationic moiety.

11. A resist film formed of the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 .

12. A pattern forming method, comprising:

forming a resist film on a support using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ;

exposing the resist film; and

developing the exposed resist film with a developer.

13. A method for manufacturing an electronic device, the method comprising the pattern forming method according to claim 12 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2021
From: ASAKAWA, DAISUKE; KAWASHIMA, TAKASHI; GOTO, AKIYOSHI; SHIRAKAWA, MICHIHIRO; YAMAMOTO, KEI
To: FUJIFILM CORPORATION
Reel/Frame 056539/0205 →
Priority Claims (1)
JP 2018-239960 · Dec 21, 2018 · national
Continuity (2)
Continuation PCTJP2019047718 · Dec 5, 2019
Related Publication 20210318616A1 · Oct 14, 2021