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

Patent metadata

Field	Value
Publication number	US-9291897-B2
Application number	US-201514605292-A
Country	US
Kind code	B2
Filing date	Jan 26, 2015
Priority date	Jul 27, 2012
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

There is provided a pattern forming method comprising, in order, (1) a step of forming a film by using an actinic ray-sensitive or radiation-sensitive resin composition containing (Ab) a resin having specific repeating units, (2) a step of exposing the film by using an electron beam or an extreme-ultraviolet ray, and (3) a step of developing the exposed film by using an organic solvent-containing developer to form a negative pattern.

First claim

The invention claimed is:

1. A pattern forming method comprising, in order,
(1) a step of forming a film by using an actinic ray-sensitive or radiation-sensitive resin composition containing a compound capable of generating an acid upon irradiation with an actinic ray or radiation, a resin (Ab) having a repeating unit represented by the following formula (Ab1) and a repeating unit represented by the following formula (A), and a solvent,
(2) a step of exposing the film, and
(3) a step of developing the exposed film by using an organic solvent-containing developer to form a negative pattern:

wherein in formula (Ab1),
R′ represents a hydrogen atom or an alkyl group,
L 1 represents a hydrogen atom or an alkyl group, L 1 may combine with L to form a ring and in this case, L 1 represents an alkylene group or a carbonyl group,
L represents a single bond or a divalent linking group, and when L 1 and L combine to form a ring, L represents a trivalent linking group,
R 1 represents a hydrogen atom or a monovalent substituent,
R 2 represents a monovalent substituent, and R 1 and R 2 may combine with each other to form a ring, and
R 3 represents a hydrogen atom, an alkyl group or a cycloalkyl group;

wherein in formula (A),
each of R 41 , R 42 and R 43 independently represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, provided that R 42 may combine with Ar 4 or X 4 to form a ring and in this case, R 42 represents a single bond or an alkylene group,
X 4 represents a single bond, an alkylene group, —COO— or —CONR 64 —, wherein R 64 represents a hydrogen atom or an alkyl group,
L 4 represents a single bond, —COO— or an alkylene group,
Ar 4 represents an (n+1)-valent aromatic ring group and in the case of combining with R 42 to form a ring, Ar 4 represents an (n+2)-valent aromatic ring group, and
n represents an integer of 1 to 4.

2. The pattern forming method as claimed in claim 1 ,
wherein the repeating unit represented by formula (A) is a repeating unit represented by the following formula (A1) or (A2):

wherein in formula (A2),
R″ represents a hydrogen atom or a methyl group.

3. The pattern forming method as claimed in claim 1 ,
wherein the content of the repeating unit represented by formula (A) is from 20 to 40 mol % based on all repeating units in the resin (Ab).

4. The pattern forming method as claimed in claim 1 ,
wherein in formula (Ab1), L 1 represents a hydrogen atom.

5. The pattern forming method as claimed in claim 1 ,
wherein in formula (Ab1), R 2 represents an alkyl group or a cycloalkyl group.

6. The pattern forming method as claimed in claim 1 ,
wherein in formula (Ab1), R 3 represents a hydrogen atom.

7. The pattern forming method as claimed in claim 1 ,
wherein in formula (Ab1), L represents a single bond, an aromatic ring group, a norbornane ring group or an adamantane ring group.

8. The pattern forming method as claimed in claim 1 ,
wherein the repeating unit represented by formula (Ab1) is a repeating unit represented by any one of the following formulae (Ab1-1) to (Ab1-4):

wherein in formula (Ab1-1),
R′ 1 represents a hydrogen atom or a methyl group, and
R 11 , R 12 and R 13 have the same meanings as R 1 , R 2 and R 3 in formula (Ab1), respectively;

wherein in formula (Ab1-2),
R′ 2 represents a hydrogen atom or a methyl group, and
R 21 , R 22 and R 23 have the same meanings as R 1 , R 2 and R 3 in formula (Ab1), respectively;

wherein in formula (Ab1-3),
R′ 3 represents a hydrogen atom or a methyl group, and
R 31 , R 32 and R 33 have the same meanings as R 1 , R 2 and R 3 in formula (Ab1), respectively; and

wherein in formula (Ab1-4),
L′ represents a single bond or a divalent linking group, and
R 41 , R 42 and R 43 have the same meanings as R 1 , R 2 and R 3 in formula (Ab1), respectively.

9. The pattern forming method as claimed in claim 1 ,
wherein the exposure is exposure to an electron beam or an extreme-ultraviolet ray.

10. The pattern forming method as claimed in claim 1 , wherein the repeating unit represented by formula (Ab1) is a repeating unit represented by formula (Ab1-c):

wherein in formula (Ab1-c),
R c ′ represents a hydrogen atom or an alkyl group,
L c represents a single bond or a divalent linking group,
R 1a ′ represents a hydrogen atom or a monovalent substituent,
R 2c represents a monovalent substituent, and R 1a ′ and R 2c may combine with each other to form a ring, and
R 3c represents a hydrogen atom, an alkyl group or a cycloalkyl group.

11. A method for manufacturing an electronic device, comprising:
(1) providing a substrate selected from a silicon- or silicon dioxide-coated substrate,
(2) forming a film on the substrate using an actinic ray-sensitive or radiation-sensitive resin composition containing a compound capable of generating an acid upon irradiation with an actinic ray or radiation, a resin (Ab) having a repeating unit represented by the following formula (Ab1) and a repeating unit represented by the following formula (A), and a solvent,
(3) exposing the film, and
(4) developing the exposed film by using an organic solvent-containing developer to form a negative pattern on the substrate:

wherein in formula (Ab1),
R′ represents a hydrogen atom or an alkyl group,
L 1 represents a hydrogen atom or an alkyl group, L 1 may combine with L to form a ring and in this case, L 1 represents an alkylene group or a carbonyl group,
L represents a single bond or a divalent linking group, and when L 1 and L combine to form a ring, L represents a trivalent linking group,
R 1 represents a hydrogen atom or a monovalent substituent,
R 2 represents a monovalent substituent, and R 1 and R 2 may combine with each other to form a ring, and
R 3 represents a hydrogen atom, an alkyl group or a cycloalkyl group;

wherein in formula (A),
each of R 41 , R 42 and R 43 independently represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, provided that R 42 may combine with Ar 4 or X 4 to form a ring and in this case, R 42 represents a single bond or an alkylene group,
X 4 represents a single bond, an alkylene group, —COO— or —CONR 64 —, wherein R 64 represents a hydrogen atom or an alkyl group,

Assignees

• Fujifilm Corp

Inventors

• Hirano Shuji
• Yokokawa Natsumi
• Takizawa Hiroo
• Nihashi Wataru

Classifications

• C08F212/30

  Sulfur · CPC title

• C08F212/24 Primary

  Phenols or alcohols · CPC title

• C08F212/20

  Fluorine · CPC title

• H10P76/2041

  Photolithographic processes · CPC title

• G03F7/0392

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