Curable composition, film, and method of producing film

Patent metadata

Field	Value
Publication number	US-10208183-B2
Application number	US-201414906079-A
Country	US
Kind code	B2
Filing date	Aug 27, 2014
Priority date	Aug 30, 2013
Publication date	Feb 19, 2019
Grant date	Feb 19, 2019

Abstract

Provided is a curable composition, including a polymerization initiator; a polymerizable compound; and an internal addition type release agent having a hydrophilic functional group, in which the internal addition type release agent is prevented from being unevenly distributed in a gas-liquid interface of the curable composition.

First claim

The invention claimed is:

1. A curable composition, which is suitable for use in imprinting, the curable composition comprising:
a polymerization initiator;
a radically polymerizable compound; and
an internal addition type release agent having a hydrophilic functional group,
wherein the internal addition type release agent is prevented from being unevenly distributed in a gas-liquid interface of the curable composition, and
wherein the internal addition type release agent is a compound represented by formula (A):
R—(OR′) n —X  (A),

wherein, in the formula (A), R represents an alkyl group having 10 to 20 carbon atoms, OR′ represents an oxyethylene group, X represents a hydroxyl group, and n represents an integer of 3 to 30.

2. A curable composition, which is suitable for use in imprinting, the curable composition comprising:
a polymerization initiator;
a radically polymerizable compound; and
an internal addition type release agent having a hydrophilic functional group,
wherein the internal addition type release agent is a compound represented by formula (A):
R—(OR′) n —X  (A),

wherein, in the formula (A), R represents an alkyl group having 10 to 20 carbon atoms, OR′ represents an oxyethylene group, X represents a hydroxyl group, and n represents an integer of 3 to 30, and
wherein the curable composition satisfies formula (1):
−5%≤{(γ 1 −γ 2 )/γ 1 }≤5%  (1),

wherein, in the formula (1), γ 1 represents a surface tension of the curable composition at 25° C., and γ 2 represents a surface tension of a curable composition for evaluation at 25° C., the curable composition for evaluation having the same composition as that of the curable composition except that the curable composition for evaluation is free of the internal addition type release agent.

3. The curable composition according to claim 1 , wherein the curable composition satisfies formula (1):
−5%{(γ 1 −γ 2 )/γ 1 }≤5%  (1),

wherein, in the formula (1), γ 1 represents a surface tension of the curable composition at 25° C., and γ 2 represents a surface tension of a curable composition for evaluation at 25° C., the curable composition for evaluation having the same composition as that of the curable composition except that the curable composition for evaluation is free of the internal addition type release agent.

4. The curable composition according to claim 1 , wherein the curable composition satisfies formula (2):
γ 1 cos θ≥30 mJ/m 2   (2),

wherein, in the formula (2), γ 1 represents a surface tension of the curable composition at 25° C., and θ represents a contact angle between a mold and the curable composition.

5. The curable composition according to claim 1 , wherein the polymerization initiator comprises a photopolymerization initiator.

6. A method of producing a film having a predetermined pattern shape and placed on a substrate, the method comprising:
a placing step of placing a curable composition on the substrate;
a mold contact step of bringing a mold having a hydrophilic surface and the curable composition into contact with each other;
a curing step of curing the curable composition with one of light and heat to produce a cured film; and
a releasing step of releasing the mold from the cured film,
wherein the curable composition comprises a polymerization initiator, a polymerizable compound, and an internal addition type release agent having a hydrophilic functional group,
wherein the internal addition type release agent is a compound represented by formula (A):
R—(OR′) n —X  (A),

wherein, in the formula (A), R represents an alkyl group having 10 to 20 carbon atoms, OR′ represents an oxyethylene group, X represents a hydroxyl group, and n represents an integer of 3 to 30, and
wherein the internal addition type release agent is prevented from being unevenly distributed in a gas-liquid interface of the curable composition in the placing step.

7. The method according to claim 6 , wherein the curable composition satisfies formula (1):
−5%{(γ 1 −γ 2 )/γ 1 }≤5%  (1),

wherein, in the formula (1), γ 1 represents a surface tension of the curable composition at 25° C., and γ 2 represents a surface tension of a curable composition for evaluation at 25° C., the curable composition for evaluation having the same composition as that of the curable composition except that the curable composition for evaluation is free of the internal addition type release agent.

8. The method according to claim 6 , wherein
the curable composition satisfies formula (2):
γ 1 cos θ≥30 mJ/m 2   (2),

wherein, in the formula (2), γ 1 represents a surface tension of the curable composition at 25° C., and θ represents a contact angle between the mold and the curable composition.

9. The method according to claim 6 , wherein the internal addition type release agent adsorbs to an interface at which the curable composition or the cured film comes into contact with the mold during a time period from the contact of the mold with the curable composition to the release of the mold from the cured film.

10. The method according to claim 6 , wherein the mold contact step is performed in an atmosphere containing a condensable gas.

11. The method according to claim 10 , wherein the condensable gas comprises 1,1,1,3,3-pentafluoropropane.

12. The method according to claim 10 , wherein the atmosphere containing the condensable gas comprises a mixed gas of helium and the condensable gas.

13. A method of producing a substrate with a circuit, the method comprising performing one of etching and ion implantation based on a pattern shape of a film obtained by a method of producing a film having a predetermined pattern shape and placed on a substrate to form a circuit structure on the substrate based on the pattern shape,
the method of producing the film comprising:
a placing step of placing a curable composition on the substrate;
a mold contact step of bringing a mold having a hydrophilic surface and the curable composition into contact with each other;
a curing step of curing the curable composition with one of light and heat to produce a cured film; and
a releasing step of releasing the mold from the cured film,
wherein the curable composition comprises a polymerization initiator, a polymerizable compound, and an internal addition type release agent having a hydrophilic functional group,
wherein the internal addition type release agent is a compound represented by formula (A):
R—(OR′) n —X  (A),

wherein, in the formula (A), R represents an alkyl group having 10 to 20 carbon atoms, OR′ represents an oxyethylene group, X represents a hydroxyl group, and n represents an integer of 3 to 30, and
wherein the internal addition type release agent is prevented from being unevenly distributed in a gas-liquid interface of the curable composition in the placing step.

14. An optical member, comprising:
a substrate; and
a film placed on the substrate,
wherein the film is a cured film produced by a method of producing a film having a predetermined pattern shape, the method comprising:
a placing step of placing a curable composition on the substrate;
a mold contact step of bringing a mold having a hydrophilic surface and the curable composition into contact with each other;
a curing step of curing the curable composition with one of light and heat to produce a cured film; and
a releasing step of releasing the mold from the cured film,
wherein the curable composition comprises a polymerization initiator, a polymerizable compound, and an internal addition type release agent having a hydrophilic functional group,
wherein the internal

Assignees

• Canon Kk

Inventors

• Kitagawa Kenji
• Ito Toshiki
• Yonezawa Shiori
• Kawasaki Youji

Classifications

• C08K5/06

  Ethers; Acetals; Ketals; Ortho-esters · CPC title

• G03F7/027

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

• H05K3/0023

  by exposure and development of a photosensitive insulating layer · CPC title

• C08K5/0008 Primary

  Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59 · CPC title

• H05K3/064

  Photoresists · CPC title