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

Patent metadata

Field	Value
Publication number	US-9291892-B2
Application number	US-201414297948-A
Country	US
Kind code	B2
Filing date	Jun 6, 2014
Priority date	Dec 27, 2011
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

Disclosed are an actinic ray-sensitive or radiation-sensitive resin composition including (A) a compound capable of generating an acid by irradiation of actinic rays or radiation, and (B) a resin of which solubility in an alkali developer increases by being decomposed by the action of an acid, and, a resist film, a pattern forming method, an electronic device manufacturing method, and an electronic device, each using the composition, wherein the actinic ray-sensitive or radiation-sensitive resin composition contains at least one type of a specific compound represented by General Formula (A-I) and at least one type of a specific compound represented by General Formula (A-II) as the compound (A).

First claim

What is claimed is:

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:
(A) a compound capable of generating an acid by irradiation of actinic rays or radiation; and
(B) a resin of which solubility in an alkali developer increases by being decomposed by the action of an acid,
wherein the actinic ray-sensitive or radiation-sensitive resin composition contains at least one type of a compound represented by the following General Formula (A-I) and at least one type of a compound represented by the following General Formula (A-II) as the compound (A),

wherein in General Formula (A-I), R 1 represents an alkyl group, a monovalent alicyclic hydrocarbon group, an aryl group or a heteroaryl group, R 2 is a divalent linking group, Rf is a fluorine atom, or an alkyl group substituted with at least one fluorine atom, n 1 and n 2 each independently are 0 or 1, and M 1 + is a sulfonium cation represented by the following General Formula (A-III),

wherein in General Formula (A-III), each Ar independently represents an aryl group or a heteroaryl group,

wherein in General Formula (A-II), R 1 ′ represents an alkyl group, a monovalent alicyclic hydrocarbon group, an aryl group or a heteroaryl group, R 2 ′ is a divalent linking group, Rf′ is a fluorine atom, or an alkyl group substituted with at least one fluorine atom, n 1 ′ and n 2 ′ each independently are 0 or 1, and M 2 + is a sulfonium cation represented by the following General Formula (A-IV) or (A-V),

wherein in General Formula (A-IV), X represents —CR 21 ═CR 22 —, —NR 23 —, —S— or —O—, R 21 , R 22 and R 23 each independently represents a hydrogen atom, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an acyl group or an aryl group, R IV represents a substituent, R IV s may be the same as or different from each other when present in plural number, n 3 represents an integer of 0 to 3, n 4 represents an integer of 0 to 9, and Y represents a structure represented by any of the following General Formulae (A-VI-1) to (A-VI-3),

wherein in General Formulae (A-VI-1) to (A-VI-3), R A represents a substituent, R A s may be the same as or different from each other when present in plural number, n A represents an integer of 0 to 12, n A ′ represents an integer of 0 to 6, each n A ″ independently represents an integer of 0 to 4, n 5 represents an integer of 0 to 3, * represents an atomic bonding, and
in General Formula (A-V), R 24 represents an aryl group, and R 25 , R 26 , R 27 and R 28 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an allyl group or a vinyl group, and R 25 and R 26 , and R 27 and R 28 may be bonded to each other to form a ring, and
wherein the ratio of the compound represented by (A-I) and the compound represented by (A-II) is 30/70 to 10/90 in terms of the compound represented by (A-I)/the compound represented by (A-II).

2. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the anion structure of the compound represented by General Formula (A-I) and the anion structure of the compound represented by General Formula (A-II) are the same.

3. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the resin (B) contains a repeating unit having a lactone structure or a sultone structure represented by the following General Formula (VI),

wherein in General Formula (VI), B represents an ester bond (a group represented by —COO—) or an amide bond (a group represented by —CONH—), R 0 represents an alkylene group, a cycloalkylene group or a combination thereof, R 0 s may be the same as or different from each other when present in plural number, and Z represents a single bond, an ether bond, an ester bond, an amide bond, a urethane bond,

or a urea bond,

Zs may be the same as or different from each other when present in plural number, each R independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, R 8 represents a monovalent organic group having a lactone structure or a sultone structure, n is the number of repetitions of the structure represented by —R 0 —Z— and represents an integer of 0 to 2, and R 7 represents a hydrogen atom, a halogen atom or an alkyl group.

4. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 2 ,
wherein the resin (B) contains a repeating unit having a lactone structure or a sultone structure represented by the following General Formula (VI),

wherein in General Formula (VI), B represents an ester bond (a group represented by —COO—) or an amide bond (a group represented by —CONH—), R 0 represents an alkylene group, a cycloalkylene group or a combination thereof, R 0 s may be the same as or different from each other when present in plural number, and Z represents a single bond, an ether bond, an ester bond, an amide bond, a urethane bond,

or a urea bond,

Zs may be the same as or different from each other when present in plural number, each R independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, R 8 represents a monovalent organic group having a lactone structure or a sultone structure, n is the number of repetitions of the structure represented by —R 0 —Z— and represents an integer of 0 to 2, and R 7 represents a hydrogen atom, a halogen atom or an alkyl group.

5. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 3 ,
wherein n is 1 or 2 in General Formula (VI).

6. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the resin (B) contains a repeating unit having an alicyclic hydrocarbon structure substituted with a hydroxyl group or a cyano group.

7. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 4 ,
wherein the resin (B) contains a repeating unit having an alicyclic hydrocarbon structure substituted with a hydroxyl group or a cyano group.

8. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the resin (B) contains a repeating unit represented by the following General Formula (AI),

wherein in General Formula (AI), Xa 1 represents a hydrogen atom, a methyl group which may have a substituent, or a group represented by —CH 2 —R 11 , R 11 represents a hydroxyl group or a monovalent

Assignees

• Fujifilm Corp

Inventors

• Shibuya Akinori
• Iwato Kaoru

Classifications

• G03F7/20

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

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title

• G03F7/0045 Primary

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

• G03F7/004 Primary

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

• G03F7/11

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