Pattern forming method, actinic ray-sensitive or radiation-sensitive resin composition, resist film, manufacturing method of electronic device, electronic device and compound

Patent metadata

Field	Value
Publication number	US-9523912-B2
Application number	US-201514840654-A
Country	US
Kind code	B2
Filing date	Aug 31, 2015
Priority date	Mar 1, 2013
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

There is provided a pattern forming method comprising (i) a step of forming a film containing an actinic ray-sensitive or radiation-sensitive resin composition containing (A) a compound represented by the specific formula, (B) a compound different from the compound (A) and capable of generating an acid upon irradiation with an actinic ray or radiation, and (P) a resin that does not react with the acid generated from the compound (A) and is capable of decreasing the solubility for an organic solvent-containing developer by the action of the acid generated from the compound (B), (ii) a step of exposing the film, and (iii) a step of developing the exposed film by using an organic solvent-containing developer to form a negative pattern; the actinic ray-sensitive or radiation-sensitive resin composition above; a resist film using the composition.

First claim

The invention claimed is:

1. A pattern forming method comprising:
(i) a step of forming a film containing an actinic ray-sensitive or radiation-sensitive resin composition containing (A) a compound represented by the following formula (I-1), (B) a compound different from the compound (A) and capable of generating an acid upon irradiation with an actinic ray or radiation, and (P) a resin that does not react with the acid generated from the compound (A) and is capable of decreasing the solubility for an organic solvent-containing developer by the action of the acid generated from the compound (B),
(ii) a step of exposing the film, and
(iii) a step of developing the exposed film by using an organic solvent-containing developer to form a negative pattern:

wherein
each of R 1 and R 1 ′ independently represents a monovalent organic group,
Y represents —SO 2 — or —CO—, and
X + represents a counter cation.

2. The pattern forming method as claimed in claim 1 ,
wherein the compound (A) is represented by the following formula (I-2a) or (I-2b):

wherein
each R 2 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkoxy group,
R 3 represents a hydrogen atom or a monovalent organic group,
two or more members out of two R 2 and R 3 may combine with each other to form a ring, and
R 1 , R 1 ′ and X + have the same meanings as R 1 , R 1 ′ and X + in formula (I-1).

3. The pattern forming method as claimed in claim 2 ,
wherein the compound (A) is represented by the following formula (I-3a) or (I-3b):

wherein
each of R 4 and R 5 independently represents a fluorine atom, a hydroxyl group, an alkyl group or a cycloalkyl group,
CH 2 contained in the alkyl group or cycloalkyl group represented by R 4 and R 5 may be replaced by —O—, —C(O)—, —S(O) n —, —S(O) 2 —NR 6 —, —C(O)—NR 6 —, —OC(O)—NR 6 — or a combination thereof,
R 6 represents a hydrogen atom or a monovalent organic group, n represents an integer of 0 to 2,
two or more members out of two R 2 and R 4 may combine with each other to form a ring, and
R 2 and X + have the same meanings as R 2 and X + in formula (I-2a).

4. The pattern forming method as claimed in claim 1 ,
wherein the resin (P) contains a repeating unit represented by the following formula (II):

wherein
Ra represents a hydrogen atom or an alkyl group,
each Rb independently represents an alkyl group or a cycloalkyl group, and two Rb may combine with each other to form a ring.

5. The pattern forming method as claimed in claim 1 , wherein the resin (P) does not contain a repeating unit capable of decomposing by the action of an acid to produce an alcoholic hydroxyl group.

6. An actinic ray-sensitive or radiation-sensitive resin composition containing:
(A) a compound represented by formula (I-1),
(B) a compound different from the compound (A) and capable of generating an acid upon irradiation with an actinic ray or radiation, and
(P) a resin that does not react with the acid generated from the compound (A) and is capable of decomposing by the action of the acid generated from the compound (B) to produce a polar group:

wherein
each of R 1 and R 1 ′ independently represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group, wherein each group may have, as a substituent, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxy group, a carbonyl group, a cycloalkyl group, an aryl group, an alkoxy group, an acyl group, an acyloxy group, an alkoxycarbonyl group, a silicon atom-containing group, or a group formed by combining two or more thereof, and when each of R 1 and R 1 ′ independently represents an aryl group, a cycloalkyl group, or an aralkyl group, the group may have, as a substituent, an alkyl group,
Y represents —SO 2 — or —CO—, and
X + represents a counter cation.

7. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 6 ,
wherein the compound (A) is represented by the following formula (I-2a) or (I-2b):

wherein
each R 2 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkoxy group,
R 3 represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxy group, a carbonyl group, a cycloalkyl group, an aryl group, an alkoxy group, an acyl group, an acyloxy group, or an alkoxycarbonyl group,
two or more members out of two R 2 and R 3 may combine with each other to form a ring, and
R 1 , R 1 ′ and X + have the same meanings as R 1 , R 1 ′ and X + in formula (I-1).

8. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 7 ,
wherein the compound (A) is represented by the following formula (I-3a) or (I-3b):

wherein
R 4 represents a fluorine atom, a hydroxyl group, an alkyl group or a cycloalkyl group,
R 5 represents an alkyl group or a cycloalkyl group, wherein each group may have, as a substituent, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxy group, a carbonyl group, a cycloalkyl group, an aryl group, an alkoxy group, an acyl group, an acyloxy group, an alkoxycarbonyl group, or a silicon atom-containing group, and when R 5 represents a cycloalkyl group, it may have, as a substituent, an alkyl group,
CH 2 contained in the alkyl group or cycloalkyl group represented by R 4 and R 5 may be replaced by —O—, —C(O)—, —S(O) n —, or a combination thereof,
R 6 represents a hydrogen atom or a monovalent organic group, n represents an integer of 0 to 2, and
R 2 and X + have the same meanings as R 2 and X + in formula (I-2a).

9. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 6 ,
wherein the resin (P) contains a repeating unit represented by the following formula (II):

wherein
Ra represents a hydrogen atom or an alkyl group,
each Rb independently represents an alkyl group or a cycloalkyl group, and two Rb may combine with each other to form a ring.

10. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 6 , wherein the resin (P) does not contain a repeating unit capable of decomposing by the action of an acid to produce an alcoholic hydroxyl group.

11. A resist film formed of the actinic ray-sensitive or radiation-sensitive resin composition claimed in claim 6 .

12. A method for manufacturing an electronic device, comprising performing a pattern forming method on a substrate, wherein the pattern forming method comprises:
(i) a step of coating the substrate with an actinic ra

Assignees

• Fujifilm Corp

Inventors

• Kataoka Shohei
• Shibuya Akinori
• Fukuhara Toshiaki
• Furutani Hajime
• Shirakawa Michihiro

Classifications

• H10P76/2042

  using lasers · CPC title

• C07C311/03

  having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07C25/18

  Polycyclic aromatic halogenated hydrocarbons · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• C07C311/51

  Y being a hydrogen or a carbon atom · CPC title