Photocurable composition and method of manufacturing film using the composition

Patent metadata

Field	Value
Publication number	US-9541826-B2
Application number	US-201314419382-A
Country	US
Kind code	B2
Filing date	Sep 20, 2013
Priority date	Sep 24, 2012
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

A photocurable composition of the present invention to be used for manufacturing a film with high productivity is a photocurable composition to be used for manufacturing a film having a predetermined pattern shape by curing the photocurable composition with light under a state where the photocurable composition is brought into contact with a mold having concavo-convex on a surface thereof, the photocurable composition including: a polymerizable compound; a photopolymerization initiator; a photosensitive gas generating agent for generating a gas through light stimulation; and a gas generation promotor for increasing an aggregation rate of the gas generated from the photosensitive gas generating agent at an interface between the mold and the photocurable composition, in which the gas generation promotor includes a fluorine atom-containing surfactant that is free of a polymerizable substituent.

First claim

The invention claimed is:

1. A photocurable composition to be used for manufacturing a film having a predetermined pattern shape by curing the photocurable composition with light under a state where the photocurable composition is brought into contact with a mold having concavo-convex on a surface thereof, the photocurable composition comprising:
a polymerizable compound;
a photopolymerization initiator;
a photosensitive gas generating agent for generating a gas through light stimulation, which does not generate a base through a photoreaction; and
a gas generation promoter for increasing an aggregation rate of the gas generated from the photosensitive gas generating agent at an interface between the mold and the photocurable composition,
wherein the gas generation promoter comprises a fluorine atom-containing surfactant that is free of a polymerizable substituent.

2. The photocurable composition according to claim 1 , wherein:
the photosensitive gas generating agent is contained at 1 wt % to 15 wt % with respect to a total weight of the polymerizable compound; and
the gas generation promoter is contained at 0.005 wt % to 3 wt % with respect to the total weight of the polymerizable compound.

3. The photocurable composition according to claim 1 , wherein the gas generation promoter comprises a compound represented by formula (1):
Rf 1 -Rc 1 -X 1   (1),

wherein, in the formula (1), Rf 1 represents a monovalent functional group constituted of a fluorine atom and a carbon atom, Rc 1 represents a divalent functional group constituted of a hydrogen atom, an oxygen atom, and a carbon atom, and X 1 represents a hydroxyl group, a carboxyl group, a sulfo group, an amino group, or an alkoxy group.

4. The photocurable composition according to claim 1 , wherein the gas generation promoter comprises a compound represented by formula (2):
Rf 1 -Rc 1 -Rf 2   (2),

wherein, in the formula (2), Rf 1 and Rf 2 each represent a monovalent functional group constituted of a fluorine atom and a carbon atom, and Rf 1 and Rf 2 may be identical to or different from each other, and Rc 1 represents a divalent functional group constituted of a hydrogen atom, an oxygen atom, and a carbon atom.

5. The photocurable composition according to claim 1 , wherein the gas generation promoter comprises a compound represented by formula (3):
X 1 -Rc 1 -Rf 3 -Rc 2 -X 2   (3),

wherein, in the formula (3), Rf 3 represents a divalent functional group constituted of a fluorine atom and a carbon atom, Rc 1 and Rc 2 each represent a divalent functional group constituted of a hydrogen atom, an oxygen atom, and a carbon atom, and Rc 1 and Rc 2 may be identical to or different from each other, and X 1 and X 2 each represent a hydroxyl group, a carboxyl group, a sulfo group, an amino group, or an alkoxy group, and X 1 and X 2 may be identical to or different from each other.

6. The photocurable composition according to claim 1 , wherein the gas generation promoter comprises a compound represented by formula (4):
F(CF 2 ) 6 CH 2 CH 2 (OCH 2 CH 2 ) 15 OH  (4).

7. The photocurable composition according to claim 1 , wherein the gas generation promoter comprises a compound represented by formula (5):
F(CF 2 ) 6 CH 2 (OCH 2 CH 2 ) 6 OH  (5).

8. A method of manufacturing a film, comprising:
placing the photocurable composition according to claim 1 on a substrate;
bringing the photocurable composition and a mold into contact with each other;
irradiating the photocurable composition with light; and
releasing the photocurable composition and the mold from each other after the irradiating,
wherein a film having a predetermined pattern shape is obtained on the substrate.

9. The method of manufacturing a film according to claim 8 , wherein a surface of the mold in contact with the photocurable composition comprises quartz.

10. The method of manufacturing a film according to claim 8 , wherein:
the irradiating comprises irradiating the photocurable composition with light through the mold; and
the mold has concavo-convex on a surface thereof.

11. A method of manufacturing a substrate with a circuit, comprising performing one of etching and ion implantation based on a pattern shape of a film obtained by the method according to claim 8 to form a circuit structure on the substrate based on the pattern shape.

12. An optical member comprising:
a substrate; and
a film placed on the substrate,
wherein the film comprises a film manufactured by the method according to claim 8 .

13. The method of manufacturing a film according to claim 8 , wherein the bringing the photocurable composition and the mold into contact with each other is performed in a condensable gas atmosphere.

14. The method of manufacturing a film according to claim 8 , wherein the bringing the photocurable composition and the mold into contact with each other is performed in an atmosphere of a mixed gas of a condensable gas and a noncondensable gas.

15. The photocurable composition according to claim 1 , wherein the photosensitive gas generating agent comprises at least one compound selected from the group consisting of an azo-based compound, a diazonium salt-based compound, an azido-based compound, a diazonaphthoquinone-based compound, and a diazomethanesulfonic acid-based compound.

Assignees

• Canon Kk

Inventors

• Ito Toshiki
• Iida Kenichi
• Matsufuji Naoko

Classifications

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• B29K2105/0005

  containing compounding ingredients (releasing, lubricating or separating agents B29C33/56, fibers B29K2105/08, B29K2105/12; fillers B29K2105/16, recycled material B29K2105/26) · CPC title

• C09D7/47

  Levelling agents · CPC title

• B29K2909/00

  Use of inorganic materials not provided for in groups B29K2803/00 - B29K2807/00, as mould material · CPC title