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

Patent metadata

Field	Value
Publication number	US-2024241444-A1
Application number	US-202418426343-A
Country	US
Kind code	A1
Filing date	Jan 30, 2024
Priority date	Aug 12, 2021
Publication date	Jul 18, 2024
Grant date	—

Abstract

An actinic ray-sensitive or radiation-sensitive resin composition includes: a resin (A) that has a specific repeating unit and whose polarity increases by the action of an acid; and an acidic compound (F) having an iodine atom. The resin (A) is a different compound from the acidic compound (F), and the acidic compound (F) is a nonionic compound.

First claim

What is claimed is:

1 . An actinic ray-sensitive or radiation-sensitive resin composition comprising: a resin (A) whose polarity increases by the action of an acid; and an acidic compound (F) having an iodine atom,
wherein the resin (A) is a different compound from the acidic compound (F), wherein the acidic compound (F) is a nonionic compound, and wherein the resin (A) has at least one selected from the group consisting of a repeating unit represented by general formula (3) below, a repeating unit represented by general formula (6) below, and a repeating unit represented by general formula (7) below:

wherein, in the general formula (3),
R 5 to R 7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
L 2 represents a divalent linking group;
R 8 to R 10 each independently represent an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group; and two selected from the group consisting of R 8 to R 10 may be bonded together to form a ring;

wherein, in the general formula (6),
R 22 to R 24 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
L 4 represents a single bond or a divalent linking group;
Ar 1 represents an aromatic group;
R 25 to R 27 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group;
R 26 and R 27 may be bonded together to form a ring; and
R 24 or R 25 may be bonded to Ar 1 ; and

wherein, in the general formula (7),
R 28 to R 30 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
L 5 represents a single bond or a divalent linking group;
R 31 and R 32 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group;
R 33 represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group; and
R 32 and R 33 may be bonded together to form a ring.

2 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the acidic compound (F) is a compound having an aromatic group substituted with an iodine atom.

3 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the acidic compound (F) is a compound represented by the following general formula (FA1):

wherein, in the general formula (FA1),
Ar a1 represents an aromatic group;
X 1 represents a single bond or a linking group;
Q 1 represents an acidic group;
Q 1 and Ar a1 may be bonded together to form a ring;
m1 and m2 each independently represent an integer of 0 to 5, provided that m1+m2 is 1 to 6;
when X 1 represents a single bond, m2 represents 0;
m3 represents 1 or 2; and
when m3 represents 2, two Ar a1 's may be the same or different, and two X 1 's may be the same or different.

4 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the acidic compound (F) is a compound represented by the following general formula (FA2):

wherein, in the general formula (FA2),
Ar a1 represents an aromatic group;
X 2 represents a single bond or a divalent linking group;
Q 1 represents an acidic group; and
m4 represents an integer of 1 to 5.

5 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the acidic compound (F) is a compound represented by the following general formula (FA3):

wherein, in the general formula (FA3),
j represents 0 or 1;
Q 3 represents a substituent;
m4 represents an integer of 1 to 5;
m5 represents an integer of 1 or more and (6+2j−m4) or less;
m6 represents an integer of 0 or more and (6+2j−m4−m5) or less; and
each * represents a direct bond bonded to an aromatic hydrocarbon shown in the general formula (FA3).

6 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the acidic compound (F) is a compound represented by the following general formula (FA4):

wherein, in the general formula (FA4),
j represents 0 or 1;
Q 4 represents a substituent;
m4 represents an integer of 1 to 5;
m5 represents an integer of 1 or more and (6+2j−m4) or less;
m7 represents an integer of 0 or more and (6+2j−m4−m5) or less; and
each * represents a direct bond bonded to an aromatic hydrocarbon shown in general formula (FA4).

7 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the acidic compound (F) is a compound represented by the following general formula (FA5):

wherein, in the general formula (FA5),
j represents 0 or 1;
Q 4 represents a substituent;
E 1 represents a single bond or a divalent linking group;
m4 represents an integer of 1 to 5;
m8 represents an integer of 0 or more and (4+2j−m4) or less; and
each * represents a direct bond bonded to an aromatic hydrocarbon shown in the general formula (FA5).

8 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the acidic compound (F) has a pKa of 6 or less.

9 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the acidic compound (F) has a molecular weight of 1000 or less.

10 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the resin (A) has a repeating unit represented by the following general formula (A2):

wherein, in the general formula (A2),
R 101 , R 102 , and R 103 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
L A represents a single bond or a divalent linking group;
Ar A represents an aromatic group;
k represents an integer of 1 to 5;
R 102 and Ar A may be bonded together; and
when R 102 and Ar A are bonded together, R 102 represents a single bond or an alkylene group.

11 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising a compound th

Assignees

• Fujifilm Corp

Inventors

• Yamaguchi Shuhei

Classifications

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title