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

Patent metadata

Field	Value
Publication number	US-10545405-B2
Application number	US-201715685499-A
Country	US
Kind code	B2
Filing date	Aug 24, 2017
Priority date	Feb 27, 2015
Publication date	Jan 28, 2020
Grant date	Jan 28, 2020

Abstract

Provided are an actinic ray-sensitive or radiation-sensitive resin composition including a compound (A) whose dissolution rate in an alkali developer decreases by the action of an acid, a resin (B) having a group that decomposes by the action of an alkali developer to increase the solubility in the alkali developer and having at least one of a fluorine atom or a silicon atom, and a resin (C) having a phenolic hydroxyl group, different from the resin (B), an actinic ray-sensitive or radiation-sensitive film and a mask blank, each formed using the actinic ray-sensitive or radiation-sensitive resin composition, a pattern forming method using the actinic ray-sensitive or radiation-sensitive resin composition, and a method for manufacturing an electronic device.

First claim

What is claimed is:

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:
a resin [N-A] whose dissolution rate in an alkali developer decreases by the action of an acid;
a resin (B) having a group that decomposes by the action of an alkali developer to increase the solubility in the alkali developer and having at least one of a fluorine atom or a silicon atom;
a resin (C) having a phenolic hydroxyl group, different from the resin (B),
wherein the resin [N-A] has at least one of a repeating unit represented by General Formula (L-1) or a repeating unit represented by General Formula (L-2):

wherein,
R L1 represents a hydrogen atom, an alkyl group, or a cycloalkyl group;
p represents 1 or 2;
q represents an integer represented by (2-p);
* represents a bonding arm to another atom constituting the repeating unit (L-1);
in a case where p is 2, or r is 2 or more, a plurality of R L1 's may be the same as or different from each other;
R L2 , R L3 , and R L4 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
X 1 represents a single bond, or a r+1-valent group selected from the group consisting of:
a linear or branched hydrocarbon group, a cyclic hydrocarbon group which may contain a heteroatom as a ring member, —O—, —S—, —CO—, —SO 2 —, —NR—, and a group formed by combining these members;
R represents a hydrogen atom, an alkyl group, or a group represented by —CH 2 OR L1 wherein R L1 has the same definition as R L1 ;
r represents an integer of 1 to 5, provided that in a case where X 1 is a single bond, r is 1;

wherein,
R 1 represents a hydrogen atom, a methyl group, or a halogen atom;
R 2 and R 3 each independently represent a hydrogen atom, an alkyl group, or a cycloalkyl group;
L represents a divalent linking group or a single bond;
Y represents a monovalent substituent excluding a methylol group;
Z represents a hydrogen atom or a monovalent substituent;
m represents an integer of 0 to 4;
n represents an integer of 1 to 5;
m+n is 5 or less;
in a case where m is 2 or more, a plurality of Y's may be the same as or different from each other, and a plurality of Y's may be bonded to each other to form a ring structure; and
in a case where n is 2 or more, a plurality of R 2 's, R 3 's, and Z's, may be the same as or different from each other;
and a compound that generates an acid upon irradiation with actinic ray or radiation.

2. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the resin (C) having a phenolic hydroxyl group has a repeating unit represented by General Formula (30),

in General Formula (30),
R 31 , R 32 , and R 33 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, R 33 may be bonded to Ar 3 to form a ring, and R 33 in this case represents an alkylene group,
X 3 represents a single bond or a divalent linking group,
Ar 3 represents an (n3+1)-valent aromatic ring group, and in a case of being bonded to R 33 to form a ring, Ar 3 represents an (n3+2)-valent aromatic ring group, and
n3 represents an integer of 1 to 4.

3. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the group that decomposes by the action of an alkali developer in the resin (B) to increase the solubility in the alkali developer is a group represented by X in a partial structure represented by General Formula (KA-1) or (KB-1),

in General Formula (KA-1) or (KB-1), X represents —COO—, —C(O)OC(O)—, —NHCONH—, —COS—, —OC(O)O—, —OSO 2 O—, or —SO 2 O—, and
Y 1 and Y 2 may be the same as or different from each other, and represent an electron-withdrawing group.

4. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the compound that generates an acid upon irradiation with actinic ray or radiation is a sulfonium salt.

5. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising a basic compound or ammonium salt compound whose basicity decreases upon irradiation with actinic ray or radiation.

6. An actinic ray-sensitive or radiation-sensitive film formed using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 .

7. A mask blank comprising the actinic ray-sensitive or radiation-sensitive film according to claim 6 .

8. A pattern forming method comprising:
a step of applying the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 onto a substrate to form a film;
a step of exposing the film; and
a step of developing the exposed film to form a negative tone pattern.

9. The pattern forming method according to claim 8 , wherein
the step of exposing the film is performed with electron beams or extreme ultraviolet rays.

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

11. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein R L1 in the General Formula (L-1) represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

12. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein R L1 in the General Formula (L-1) represents a cycloalkyl group having 3 to 17 carbon atoms which may be either monocyclic or polycyclic.

13. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the repeating unit represented by General Formula (L-1) is any one of the following:

wherein R and R′ each represent a hydrogen atom or a methyl group.

14. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein L in the General Formula (L-2) is a divalent aromatic ring group or a linking group represented by —COO—.

15. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the repeating unit represented by General Formula (L-2) is any one of the following:

wherein Ac represents an acetyl group; and Me represents a methyl group.

16. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the actinic-ray sensitive or radiation-sensitive resin composition further comprises a low molecular compound [N-C] whose dissolution rate in an alkali developer decreases by the action of an acid.

17. The actinic ray-sensitive or radiation-sensitiv

Assignees

• Fujifilm Corp

Inventors

• Yamaguchi Shuhei
• Takahashi Koutarou
• Fukuhara Toshiaki
• Hirano Shuji

Classifications

• C08F212/24

  Phenols or alcohols · CPC title

• C08F112/24

  Phenols or alcohols · CPC title

• C08F220/302

  and two or more oxygen atoms in the alcohol moiety · CPC title

• C08F220/281

  and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate · CPC title

• C08F220/282

  and containing two or more oxygen atoms · CPC title