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

Patent metadata

Field	Value
Publication number	US-2023148344-A1
Application number	US-202218059329-A
Country	US
Kind code	A1
Filing date	Nov 28, 2022
Priority date	May 29, 2020
Publication date	May 11, 2023
Grant date	—

Abstract

The present invention provides an actinic ray-sensitive or radiation-sensitive resin composition with which a pattern having excellent LWR performance can be obtained, a resist film, a pattern forming method, a method for manufacturing an electronic device, a compound, and a method for producing the compound. The actinic ray-sensitive or radiation-sensitive resin composition of an embodiment of the present invention is an actinic ray-sensitive or radiation-sensitive resin composition including a resin having a repeating unit having a group having a polarity that increases through decomposition by the action of an acid, in which the actinic ray-sensitive or radiation-sensitive resin composition further includes, in addition to the resin, a compound having at least one cation represented by General Formula (1), or the resin further has, in addition to the repeating unit, a repeating unit having the cation represented by General Formula (1).(Rd1)m—[Xd1]+-(Ld1-Ard1—(S—Xd2)p)n   (1)

First claim

What is claimed is:

1 . An actinic ray-sensitive or radiation-sensitive resin composition comprising a resin having a repeating unit having a group having a polarity that increases through decomposition by an action of an acid,
wherein the actinic ray-sensitive or radiation-sensitive resin composition further includes, in addition to the resin, a compound having at least one cation represented by General Formula (1), or the resin further has, in addition to the repeating unit, a repeating unit having a cation represented by General Formula (1),
(R d1 ) m − [X d1 ] + -(L d1 -Ar d1 —(S—X d2 ) p ) n    (1)

in General Formula (1), X d1 represents a sulfur atom or an iodine atom, R d1 represents a linear, branched, or cyclic alkyl group which may have a substituent, a linear, branched, or cyclic alkenyl group which may have a substituent, or an aryl group which may have a substituent, in a case where m represents 2, two Rd's may be bonded to each other to form a ring, L d1 represents a single bond or a divalent linking group, Ar d1 represents an aromatic hydrocarbon ring group which may have a substituent, and X d2 represents a group represented by General Formula (1-1) or a leaving group that leaves by an action of an acid,
*-L d2 -R d2   General Formula (1-1)

in General Formula (1-1), L d2 represents a single bond or a divalent linking group, R d2 represents a group having a polarity that increases through decomposition by an action of an acid, * represents a bonding position, in a case where X d1 represents the sulfur atom, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m+n is 3, in a case where X d1 represents the iodine atom, n represents 1 or 2, m represents 0 or 1, and m+n is 2, and p represents an integer of 1 to 5.

2 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the actinic ray-sensitive or radiation-sensitive resin composition has a compound having at least one cation represented by General Formula (1), and the compound having at least one cation represented by General Formula (1) includes at least one selected from the group consisting of a compound represented by General Formula (2) and a compound represented by General Formula (3),
Z 1 + Y 1 −   General Formula (2)

in General Formula (2), Z 1 + represents the cation represented by General Formula (1), and Y 1 − represents a monovalent organic anion,
L-(-Y 2 − Z 2 + ) q    (3)

in General Formula (3), Z 2 + 's represents a cation, and at least one of Z 2 + 's represents the cation represented by General Formula (1), Y 2 − represents an anionic functional group, L represents a q-valent linking group, and q represents an integer of 2 or more.

3 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein X d1 is a sulfur atom.

4 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein in General Formula (1), the group having a polarity that increases through decomposition by an action of an acid is a group represented by General Formula (a-1),

in General Formula (a-1), R a1 represents a leaving group that leaves by an action of an acid, and * represents a bonding position.

5 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein in General Formula (1), n represents an integer of 2 or 3, or p represents an integer of 2 to 5.

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

7 . A pattern forming method comprising:
a step of forming a resist film on a substrate using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ; a step of exposing the resist film; and a step of developing the exposed resist film using a developer to form a pattern.

8 . A method for manufacturing an electronic device, comprising the pattern forming method according to claim 7 .

9 . A compound comprising at least one cation represented by General Formula (1),
(R d1 ) m − [X d1 ] + -(L d1 -Ar d1 —(S—X d2 ) p ) n    (1)

in General Formula (1), X d1 represents a sulfur atom or an iodine atom, R d1 represents a linear, branched, or cyclic alkyl group which may have a substituent, a linear, branched, or cyclic alkenyl group which may have a substituent, or an aryl group which may have a substituent, in a case where m represents 2, two R d1 's may be bonded to each other to form a ring, L d1 represents a single bond or a divalent linking group, Ar d1 represents an aromatic hydrocarbon ring group which may have a substituent, and X d2 represents a group represented by General Formula (1-1) or a leaving group that leaves by an action of an acid,
*-L d2 -R d2   General Formula (1-1)

in General Formula (1-1), L d2 represents a single bond or a divalent linking group, R d2 represents a group having a polarity that increases through decomposition by the action of an acid, * represents a bonding position,
in a case where X d1 represents the sulfur atom, n represents an integer of 1 to 3, m represents an integer of 0 to 2, and m+n is 3, in a case where X d1 represents the iodine atom, n represents 1 or 2, m represents 0 or 1, and m+n is 2, and p represents an integer of 1 to 5.

10 . The compound according to claim 9 ,
wherein the compound is a compound represented by General Formula (2) or a compound represented by General Formula (3),
Z 1 + Y 1 −   General Formula (2)

in General Formula (2), Z 1 + represents the cation represented by General Formula (1), and Y 1 − represents a monovalent organic anion,
L-(-Y 2 − Z 2 + ) q    (3)

in General Formula (3), Z 2 + 's represents a cation, and at least one of Z 2 + 's represents the cation represented by General Formula (1), Y 2 − represents an anionic functional group, L represents a q-valent linking group, and q represents an integer of 2 or more.

11 . The compound according to claim 9 ,
wherein X d1 is a sulfur atom.

12 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 9 ,
wherein in General Formula (1), the group having a polarity that increases through decomposition by an action of an acid is a group represented by General Formula (a-1),

in General Formula (a-1), R a1 represents a leaving group that leaves by an action of an acid, and * represents a bonding position.

13 . The compound according to claim 9 ,
wherein in General Formula (1), n is an integer of 2 or 3, or p is an integer of 2 to 5.

14 . A method for producing the compound having at least one cation represented by General Formula (1) according to claim 9 ,
wherein a compound having at least one cation represented by General Formula (4) is reacted with a compound represented by General Formula (5) in a presence of a basic compound to produce the compound having at least one cation represented by General Formula (1),
(R d1 ) m —[X d1 ] + -(L d1 -Ar d1 —(R d3 ) p ) n    (4)

in General Formula (4), X d1 represents a sulfur atom or an iodine atom, R d1 represents a linear, branched, or cyclic alkyl group which may have a substituent, a linear, branched, or cyclic alkenyl group which may have a substituent, or an aryl group which may have a substituent, in a case wh

Assignees

• Fujifilm Corp

Inventors

• Goto Akiyoshi
• Takada Akira
• USHIYAMA Aina
• KOJIMA Masafumi
• Shirakawa Michihiro

Classifications

• C07C309/12

  containing esterified hydroxy groups bound to the carbon skeleton · CPC title

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• C07C303/22

  from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; {from sulfonic halides by reactions not involving the formation of halosulfonyl groups} · CPC title

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title