Photocurable composition, method for forming a pattern, and method for producing a photocured product

Patent metadata

Field	Value
Publication number	US-10535519-B2
Application number	US-201715618868-A
Country	US
Kind code	B2
Filing date	Jun 9, 2017
Priority date	Feb 9, 2012
Publication date	Jan 14, 2020
Grant date	Jan 14, 2020

Abstract

It is intended to provide a photocured product that is prepared using the photo-imprint method and has favorable pattern precision and improvement in pattern defects. The present invention provides a photocured product obtained by irradiating a coating film in contact with a mold with light, the photocured product containing a fluorine atom-containing surfactant, wherein of secondary ion signals obtained by the surface analysis of the photocured product based on time-of-flight secondary ion mass spectrometry, the intensity of a C2H5O+ ion signal is higher than that of a C3H7O+ ion signal.

First claim

The invention claimed is:

1. A photocurable composition for obtaining a photocured product by irradiating the photocurable composition in contact with a mold with light, the photocurable composition comprising:
at least a polymerizable monomer;
a photopolymerization initiator; and
a fluorine atom-containing surfactant represented by:
R 1 - x 1 -R 2 - x 2 -R 3   (1),

wherein R 1 represents a perfluoroalkyl group, R 2 represents a divalent substituent containing ethylene oxide, R 3 represents a polar functional group selected from an alkylhydroxyl group, a carboxyl group, a thiol group, a pyridyl group, a silanol group, and a sulfo group, and x 1 and x 2 each represent a single bond or a divalent substituent,
wherein a ratio of the fluorine atom-containing surfactant to the photocured product is 0.001% by weight to 5% by weight, and
wherein of secondary ion signals obtained by a surface analysis of the photocured product based on time-of-flight secondary ion mass spectrometry, an intensity of a C 2 H 5 O + ion signal is higher than that of a C 3 H 7 O + ion signal.

2. The photocurable composition according to claim 1 , wherein the fluorine atom-containing surfactant is F(CF 2 ) 6 CH 2 (OCH 2 CH 2 ) 6 OH.

3. A method for forming a photocured product having a predetermined pattern shape on a substrate, the method comprising:
coating the substrate with a photocurable composition;
contacting the photocurable composition with a mold;
irradiating the photocurable composition with light via the mold; and
demolding the mold from the photocurable composition,
wherein the photocured product contains a fluorine atom-containing surfactant represented by:
R 1 - x 1 -R 2 - x 2 -R 3   (1),

wherein R 1 represents a perfluoroalkyl group, R 2 represents a divalent substituent containing ethylene oxide, R 3 represents a polar functional group selected from an alkylhydroxyl group, a carboxyl group, a thiol group, a pyridyl group, a silanol group, and a sulfo group, and x 1 and x 2 each represent a single bond or a divalent substituent,
wherein a ratio of the fluorine atom-containing surfactant to the photocured product is 0.001% by weight to 5% by weight, and
wherein of secondary ion signals obtained by a surface analysis of the photocured product based on time-of-flight secondary ion mass spectrometry, an intensity of a C 2 H 5 O + ion signal is higher than that of a C 3 H 7 O + ion signal.

4. A method for producing a circuit substrate, the method comprising:
applying a photocurable composition onto a substrate material;
pressing a mold against the photocurable composition to form a pattern in the photocurable composition;
irradiating the photocurable composition having the pattern with light to prepare a cured product having the pattern; and
releasing the mold from the cured product to form, on the substrate material, a circuit structure based on the pattern in the cured product,
wherein the cured product contains a fluorine atom-containing surfactant represented by:
R 1 - x 1 -R 2 - x 2 -R 3   (1),

wherein R 1 represents a perfluoroalkyl group, R 2 represents a divalent substituent containing ethylene oxide, R 3 represents a polar functional group selected from an alkylhydroxyl group, a carboxyl group, a thiol group, a pyridyl group, a silanol group, and a sulfo group, and x 1 and x 2 each represent a single bond or a divalent substituent,
wherein a ratio of the fluorine atom-containing surfactant to the photocured product is 0.001% by weight to 5% by weight, and
wherein of secondary ion signals obtained by a surface analysis of the photocured product based on time-of-flight secondary ion mass spectrometry, an intensity of a C 2 H 5 O + ion signal is higher than that of a C 3 H 7 O + ion signal.

5. The method according to claim 4 , wherein the circuit substrate is a semiconductor device.

6. A method for producing a cured product having an elevation/depression pattern, the method comprising:
applying a photocurable composition onto a base material;
contacting a mold having an elevated/depressed surface with the photocurable composition to form a corresponding elevation/depression pattern in the photocurable composition;
irradiating the photocurable composition having the elevation/depression pattern with light to prepare a photocured product; and
releasing the mold from the photocured product to produce the cured product having the elevation/depression pattern,
wherein the photocured product contains a fluorine atom-containing surfactant represented by:
R 1 - x 1 -R 2 - x 2 -R 3   (1),

wherein R 1 represents a perfluoroalkyl group, R 2 represents a divalent substituent containing ethylene oxide, R 3 represents a polar functional group selected from an alkylhydroxyl group, a carboxyl group, a thiol group, a pyridyl group, a silanol group, and a sulfo group, and x 1 and x 2 each represent a single bond or a divalent substituent,
wherein a ratio of the fluorine atom-containing surfactant to the photocured product is 0.001% by weight to 5% by weight, and
wherein of secondary ion signals obtained by a surface analysis of the photocured product based on time-of-flight secondary ion mass spectrometry, an intensity of a C 2 H 5 O + ion signal is higher than that of a C 3 H 7 O + ion signal.

7. A method for forming a pattern, the method comprising:
applying a photocurable composition onto a base material;
contacting a mold having an elevated/depressed surface with the photocurable composition to form a corresponding elevation/depression pattern in the photocurable composition;
irradiating the photocurable composition having the elevation/depression pattern with light to prepare a cured product having the elevation/depression pattern; and
releasing the mold from the cured product to form the pattern in the cured product,
wherein the cured product contains a fluorine atom-containing surfactant represented by:
R 1 - x 1 -R 2 - x 2 -R 3   (1),

wherein R 1 represents a perfluoroalkyl group, R 2 represents a divalent substituent containing ethylene oxide, R 3 represents a polar functional group selected from an alkylhydroxyl group, a carboxyl group, a thiol group, a pyridyl group, a silanol group, and a sulfo group, and x 1 and x 2 each represent a single bond or a divalent substituent,
wherein a ratio of the fluorine atom-containing surfactant to the photocured product is 0.001% by weight to 5% by weight, and
wherein of secondary ion signals obtained by a surface analysis of the photocured product based on time-of-flight secondary ion mass spectrometry, an intensity of a C 2 H 5 O + ion signal is higher than that of a C 3 H 7 O + ion signal.

Assignees

• Canon Kk

Inventors

• Murayama Yohei
• Ito Toshiki
• Mihara Chieko
• Okinaka Motoki

Classifications

• H10P50/692

  characterised by their composition, e.g. multilayer masks or materials · CPC title

• H10P76/2041 Primary

  Photolithographic processes · CPC title

• G03F7/11 Primary

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

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• B82Y10/00

  Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic · CPC title