Chemically amplified resist material, pattern-forming method, compound, and production method of compound

Patent metadata

Field	Value
Publication number	US-10073349-B2
Application number	US-201615241345-A
Country	US
Kind code	B2
Filing date	Aug 19, 2016
Priority date	Aug 20, 2015
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

A pattern-forming method comprises patternwise exposing a predetermined region of a resist material film made from a photosensitive resin composition comprising a chemically amplified resist material to a first radioactive ray that is ionizing radiation or nonionizing radiation having a wavelength of no greater than 400 nm. The resist material film patternwise exposed is floodwise exposed to a second radioactive ray that is nonionizing radiation having a wavelength greater than the wavelength of the nonionizing radiation for the patternwise exposing and greater than 200 nm. The chemically amplified resist material comprises a base component, and a generative component that is capable of generating a radiation-sensitive sensitizer and an acid upon an exposure. The generative component comprises a radiation-sensitive sensitizer generating agent. The radiation-sensitive sensitizer generating agent comprises a compound represented by formula (A).

First claim

The invention claimed is:

1. A pattern-forming method comprising:
patternwise exposing a predetermined region of a resist material film made from a photosensitive resin composition comprising a chemically amplified resist material to a first radioactive ray that is ionizing radiation or nonionizing radiation having a wavelength of no greater than 400 nm;
floodwise exposing the resist material film patternwise exposed, to a second radioactive ray that is nonionizing radiation having a wavelength greater than the wavelength of the nonionizing radiation for the patternwise exposing and greater than 200 nm;
baking the resist material film floodwise exposed; and
developing the resist material film baked with a developer solution to form a resist pattern,
the chemically amplified resist material comprising:
a base component that is capable of being made soluble or insoluble in the developer solution by an action of an acid; and
a generative component that is capable of generating a radiation-sensitive sensitizer and an acid upon an exposure,
wherein the generative component comprises:
a radiation-sensitive acid-and-sensitizer generating agent and a radiation-sensitive sensitizer generating agent;
the radiation-sensitive sensitizer generating agent and a radiation-sensitive acid generating agent; or
the radiation-sensitive acid-and-sensitizer generating agent, the radiation-sensitive sensitizer generating agent and the radiation-sensitive acid generating agent,
wherein
the radiation-sensitive acid-and-sensitizer generating agent generates, upon an exposure to the first radioactive ray, an acid, and a radiation-sensitive sensitizer absorbing the second radioactive ray, and substantially does not generate the acid and the radiation-sensitive sensitizer upon an exposure to the second radioactive ray in light-unexposed regions that are not exposed to the first radioactive ray in the patternwise exposing;
the radiation-sensitive sensitizer generating agent generates, upon the exposure to the first radioactive ray, a radiation-sensitive sensitizer absorbing the second radioactive ray, and substantially does not generate the radiation-sensitive sensitizer upon the exposure to the second radioactive ray in light-unexposed regions that are not exposed to the first radioactive ray in the patternwise exposing; and
the radiation-sensitive acid generating agent generates an acid upon the exposure to the first radioactive ray, and substantially does not generate the acid upon the exposure to the second radioactive ray in light-unexposed regions that are not exposed to the first radioactive ray in the patternwise exposing,
the radiation-sensitive sensitizer generating agent comprises at least one compound represented by formula (A):

wherein, in the formula (A),
R a1 and R a2 each independently represent a monovalent organic group having 1 to 20 carbon atoms, or R a1 and R a2 taken together represent a ring structure having 4 to 20 ring atoms together with O—C—O to which R a1 and R a2 bond;
R a3 and R a4 each independently represent a monovalent organic group having 1 to 20 carbon atoms, —OH, —SH, —NH 2 , —PH 2 , a halogen atom or a nitro group;
m and n are each independently an integer of 0 to 4, wherein a sum of m and n is no less than 1, wherein in a case where m is no less than 2, a plurality of R a3 s are identical or different, and at least two of the plurality of R a3 s optionally taken together represent a ring structure having 4 to 20 ring atoms together with the carbon chain to which the at least two of the plurality of R a3 s bond, and wherein in a case where n is no less than 2, a plurality of R a4 s are identical or different, and at least two of the plurality of R a4 s optionally taken together represent a ring structure having 4 to 20 ring atoms together with the carbon chain to which the at least two of the plurality of R a4 s bond; and
X represents a single bond, an oxygen atom, a sulfur atom, —CR a5 R a6 — or —NR a7 —,
wherein R a5 , R a6 and R a7 each independently represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, wherein in a case where m is no less than 1, one or a plurality of R a3 (s) and at least one of R a5 and R a6 optionally taken together represent a ring structure having 4 to 20 ring atoms together with the carbon chain to which the one or a plurality of R a3 (s) and the at least one of R a5 and R a6 bond, wherein in a case where n is no less than 1, one or a plurality of R a4 and at least one of R a5 and R a6 optionally taken together represent a ring structure having 4 to 20 ring atoms together with the carbon chain to which the one or a plurality of R a4 and the at least one of R a5 and R a6 bond, wherein in a case where m is no less than 1, one or a plurality of R a3 (s) and R a7 optionally taken together represent an aliphatic heterocyclic structure having 4 to 20 ring atoms together with the atom chain to which the one or a plurality of R a3 (s) and R a7 bond, and wherein in a case where n is no less than 1, one or a plurality of R a4 (s) and R a7 optionally taken together represent an aliphatic heterocyclic structure having 4 to 20 ring atoms together with the atom chain to which the one or a plurality of R a4 (s) and R a7 bond, and
the at least one compound represented by formula (A) is a recrystallized substance.

2. The pattern-forming method according to claim 1 , wherein the base component is a polymer solubility in a developer solution of which is capable of being altered by an action of an acid.

3. The pattern-forming method according to claim 1 , comprising the radiation-sensitive acid generating agent as the generative component.

4. The pattern-forming method according to claim 1 , comprising as the generative component, a polymer having an acid-generating group.

5. The pattern-forming method according to claim 1 , wherein the at least one compound represented by the formula (A) is derived from a compound having a benzanthrone skeleton.

6. The pattern-forming method according to claim 1 , wherein the at least one compound represented by formula (A) is represented by at least one of formulae (A-1) to (A-5):

wherein R a1 to R a7 are as defined in formula (A).

7. The pattern-forming method according to claim 6 , wherein the at least one compound represented by formula (A) is represented by formula (A-5).

8. The pattern-forming method according to claim 1 , wherein the compound represented by formula (A) is represented by formula (B-3):

9. The pattern-forming method according to claim 1 , wherein the developer solution is an alkaline developer solution.

10. The pattern-forming method according to claim 1 , wherein the at least one compound represented by formula (A) is a multiple-times recrystallized substance.

11. A chemically amplified resist material comprising:
a base component that is capable of being made soluble or insoluble in a developer solution by an action of an acid; and
a generative component that is capable of generating a radiation-sensitive sensitizer and an acid upon an exposure,
wherein the generative component comprises:
a radiation-sensitive acid-and-sensitizer generating agent and a radiation-sensitive sensitizer generating agent;
the radiation-sensitive sensitizer generating agent and a radiation-sensitiv

Assignees

• Univ Osaka
• Tokyo Electron Ltd
• Jsr Corp

Inventors

• Nakagawa Hisashi
• Naruoka Takehiko
• Nagai Tomoki
• Tagawa Seiichi
• Oshima Akihiro
• Nagahara Seiji

Classifications

• G03F7/2002

  with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image · CPC title

• C07D493/10

  Spiro-condensed systems · CPC title

• C08F220/22

  Esters containing halogen · CPC title

• G03F7/322

  Aqueous alkaline compositions · CPC title

• C07C309/07

  containing oxygen atoms bound to the carbon skeleton · CPC title