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

Patent metadata

Field	Value
Publication number	US-11467489-B2
Application number	US-202016805922-A
Country	US
Kind code	B2
Filing date	Mar 2, 2020
Priority date	Sep 20, 2017
Publication date	Oct 11, 2022
Grant date	Oct 11, 2022

Abstract

An actinic ray-sensitive or radiation-sensitive resin composition contains a compound that generates an acid upon irradiation with actinic rays or radiation and a resin whose polarity increases by the action of an acid, in which the compound is represented by a specific General Formula (X).

First claim

What is claimed is:

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:
a compound that generates an acid upon irradiation with actinic rays or radiation; and
a resin whose polarity increases by the action of an acid,
wherein the compound is represented by General Formula (X),

in General Formula (X),
A 101 represents a group that leaves by the action of an acid, and in a case where a plurality of A 101 's are present, the plurality of A 101 's may be linked to each other,
n 101 represents an integer of 1 to 4,
R 101 represents an (n 101 +1)-valent aliphatic hydrocarbon group having no heteroatom,
Y 101 represents an ether group or an ester group,
L 101 represents a linear alkylene group having no substituent,
R 102 and R 103 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atom, in which a hydrogen atom is not substituted with a fluorine atom, and
M + represents a monovalent cation.

2. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the compound has an acetal structure or a ketal structure in a moiety including A 101 and R 101 .

3. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the compound is represented by General Formula (X-1),

in General Formula (X-1),
R 311 and R 312 each independently represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a heterocyclic group,
n 301 represents an integer of 1 or 2,
R 301 represents an ((n 301 ×2)+1)-valent aliphatic hydrocarbon group having no heteroatom,
Y 101 represents an ether group or an ester group,
L 101 represents a linear alkylene group having no substituent,
R 102 and R 103 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atom, in which a hydrogen atom is not substituted with a fluorine atom, and
M + represents a monovalent cation.

4. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 3 ,
wherein R 301 represents an ((n 301 ×2)+1)-valent alicyclic hydrocarbon group having no heteroatom.

5. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the compound is represented by General Formula (X-2),

in General Formula (X-2),
R411 represents an alkyl group, an aryl group, a heteroaryl group, or a heterocyclic group,
R 412 and R 413 each independently represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a heterocyclic group,
n 401 represents an integer of 1 or 2,
R 401 represents an (n 401 +1)-valent aliphatic hydrocarbon group having no heteroatom,
Y 101 represents an ether group or an ester group,
L 101 represents a linear alkylene group having no substituent,
R 102 and R 103 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atom, in which a hydrogen atom is not substituted with a fluorine atom, and
M + represents a monovalent cation.

6. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein Y 101 represents an ether group.

7. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein M + represents a substituted or unsubstituted triphenylsulfonium cation.

8. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the resin includes a repeating unit having an acid-decomposable group,
the acid-decomposable group has a structure with a polar group being protected with a group that leaves through decomposition by the action of an acid, and
the polar group is a phenolic hydroxyl group.

9. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the resin includes a repeating unit having an acid-decomposable group,
the acid-decomposable group has a structure with a polar group being protected with a group that leaves through decomposition by the action of an acid, and
the group that leaves through decomposition by the action of an acid is represented by Formula —C(R 01 )(R 02 )(OR 39 ),
in the formula, R 39 represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group, and R 01 and R 02 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group.

10. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising a solvent.

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

12. A pattern forming method comprising:
forming a resist film with 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 .

14. An actinic ray-sensitive or radiation-sensitive resin composition comprising:
a compound that generates an acid upon irradiation with actinic rays or radiation; and
a resin whose polarity increases by the action of an acid,
wherein the compound is represented by General Formula (X-2),

in General Formula (X-2),
R 411 represents an alkyl group, an aryl group, a heteroaryl group, or a heterocyclic group,
R 412 and R 413 each independently represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a heterocyclic group,
n 401 represents an integer of 1 or 2,
R 401 represents an (n 401 +1)-valent aliphatic hydrocarbon group having no heteroatom,
Y 101 represents an ether group or an ester group,
L 101 represents an alkylene group,
R 102 and R 103 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atom, in which a hydrogen atom is not substituted with a fluorine atom, and
M + represents a monovalent cation.

15. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 14 ,
wherein M + represents a substituted or unsubstituted triphenylsulfonium cation.

16. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 14 ,
wherein the resin includes a repeating unit having an acid-decomposable group,
the acid-decomposable group has a structure with a polar group being protected with a group that leaves through decomposition by the action of an acid, and
the polar group is a phenolic hydroxyl group.

17. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 14 ,
wherein the resin includes a repeating unit having an acid-decomposable group,
the acid-decomposable group has a structure with a polar gro

Assignees

• Fujifilm Corp

Inventors

• Yagi Kazunari
• Kawashima Takashi
• Tsuchimura Tomotaka

Classifications

• C07D493/04

  Ortho-condensed systems · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title

• G03F7/0045 Primary

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

• G03F7/26

  Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence) · CPC title

• C07D233/56

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms · CPC title