Actinic ray-sensitive or radiation-sensitive resin composition, actinic ray-sensitive or radiation-sensitive film, mask blank provided with actinic ray-sensitive or radiation-sensitive film, photomask, pattern forming method, method for manufacturing electronic device, electronic device, compound, and method for producing compound

Patent metadata

Field	Value
Publication number	US-2016280621-A1
Application number	US-201615176762-A
Country	US
Kind code	A1
Filing date	Jun 8, 2016
Priority date	Feb 5, 2014
Publication date	Sep 29, 2016
Grant date	—

Abstract

The composition contains an alkali-soluble resin and a crosslinking agent that is represented by the following General Formula (I). In the formula, each of R 1 and R 6 independently represents a hydrogen atom or a hydrocarbon group having 5 or less carbon atoms; each of R 2 and R 5 independently represents an alkyl group, a cycloalkyl group, an aryl group, or an acyl group; and each of R 3 and R 4 independently represents a hydrogen atom or an organic group having 2 or more carbon atoms, and R 3 and R 4 may be bonded to each other to form a ring.

First claim

What is claimed is:

1 . An actinic ray-sensitive or radiation-sensitive resin composition comprising:
an alkali-soluble resin; and a crosslinking agent, wherein the crosslinking agent is represented by the following General Formula (I),

wherein in General Formula (I),
each of R 1 and R 6 independently represents a hydrogen atom, or a hydrocarbon group having 5 or less carbon atoms,
each of R 2 and R 5 independently represents an alkyl group, a cycloalkyl group, an aryl group, or an acyl group,
each of R 3 and R 4 independently represents a hydrogen atom, or an organic group having 2 or more carbon atoms, and
R 3 and R 4 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 R 3 and R 4 in General Formula (I) are bonded to each other to form a ring.

3 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 2 , wherein R 3 and R 4 in General Formula (I) are bonded to each other to form a ring represented by the following General Formula (I-a),

wherein in General Formula (I-a),
each of R 7 and R 8 independently represents a substituent,
each of n1 and n2 independently represents an integer of 0 to 4, and
* indicates a connecting site to the phenolic nucleus.

4 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the alkali-soluble resin is a resin having a repeating unit represented by the following General Formula (1),

wherein in General Formula (1),
R represents a hydrogen atom or a methyl group,
X represents a group having a non-acid-decomposable hydrocarbon group,
Ar represents an aromatic ring, and
L represents a divalent linking group.

5 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising a compound capable of generating an acid upon irradiation with actinic rays or radiation.

6 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 5 , wherein the compound capable of generating an acid upon irradiation with actinic rays or radiation is an onium salt.

7 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 5 , wherein the compound capable of generating an acid upon irradiation with actinic rays or radiation is a compound capable of generating an acid represented by the following General Formula (IIIB) or (IVB),

wherein in General Formula (IIIB),
each Xf independently represents a fluorine atom, or an alkyl group substituted with at least one fluorine atom,
each of R 1 and R 2 independently represents a hydrogen atom, or an alkyl group,
each L independently represents a divalent linking group,
Cy represents a cyclic organic group, and
x represents an integer of 1 to 20, y represents an integer of 0 to 10, and z represents an integer of 0 to 10, and
in General Formula (IVB),
each Xf independently represents a fluorine atom, or an alkyl group substituted with at least one fluorine atom,
each of R 1 and R 2 independently represents a hydrogen atom, or an alkyl group,
each L independently represents a divalent linking group,
Cy represents a cyclic organic group,
Rf represents a group containing a fluorine atom, and
x represents an integer of 1 to 20, y represents an integer of 0 to 10, and z represents an integer of 0 to 10.

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

9 . A mask blank provided with the actinic ray-sensitive or radiation-sensitive film according to claim 8 .

10 . A photomask produced by a method including exposing the actinic ray-sensitive or radiation-sensitive film provided in the mask blank according to claim 9 , and developing the exposed actinic ray-sensitive or radiation-sensitive film.

11 . A pattern forming method, comprising:
forming an actinic ray-sensitive or radiation-sensitive film using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ; exposing the film; and developing the exposed film using a developer to form a pattern.

12 . The pattern forming method according to claim 11 , wherein the exposure is carried out using X-rays, an electron beam, or EUV.

13 . A method for manufacturing an electronic device, comprising the pattern forming method according to claim 11 .

14 . A compound represented by the following General Formula (I-b),

wherein in General Formula (I-b),
each of R 1b and R 6b independently represents an alkyl group having 5 or less carbon atoms,
each of R 2b and R 5b independently represents an alkyl group having 6 or less carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms, and
Z represents an atomic group necessary for forming a ring together with the carbon atom in General Formula (I-b).

15 . A method for producing a compound represented by the following General Formula (I), comprising using a compound represented by the following General Formula (I-c) as a raw material,

wherein in General Formula (I),
each of R 1 and R 6 independently represents a hydrogen atom, or a hydrocarbon group having 5 or less carbon atoms,
each of R 2 and R 5 independently represents an alkyl group, a cycloalkyl group, an aryl group, or an acyl group,
each of R 3 and R 4 independently represents a hydrogen atom, or an organic group having 2 or more carbon atoms, and
R 3 and R 4 may be bonded to each other to form a ring, and

in General Formula (I-c),
R 1 , R 3 , R 4 , and R 6 have the same definitions as R 1 , R 3 , R 4 , and R 6 in General Formula (I), respectively.

Assignees

• Fujifilm Corp

Inventors

• Yokokawa Natsumi
• Mochizuki Hidehiro
• Takahashi Koutarou
• Yamaguchi Shuhei

Classifications

• G03F7/038 Primary

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

• G03F7/203

  comprising an imagewise exposure to electromagnetic radiation or corpuscular radiation · CPC title

• C07C41/22

  by introduction of halogens; by substitution of halogen atoms by other halogen atoms · CPC title

• G03F7/004 Primary

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

• G03F7/2059

  using a scanning corpuscular radiation beam, e.g. an electron beam · CPC title