Curable composition for nanoimprinting and cured product

Patent metadata

Field	Value
Publication number	US-9690193-B2
Application number	US-201615258662-A
Country	US
Kind code	B2
Filing date	Sep 7, 2016
Priority date	Mar 24, 2009
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

Disclosed is a curable composition for nanoimprinting, which includes one or more polymerizable monomers, in which one or more monofunctional radically polymerizable monomers occupy 90 percent by weight or more of the one or more polymerizable monomers, and the one or more monofunctional radically polymerizable monomers give a polymer having a glass transition temperature of 25° C. or higher. The one or more monofunctional radically polymerizable monomers are preferably at least one compound selected from (meth)acrylic ester compounds, styrenic compounds, and vinyl ether compounds.

First claim

The invention claimed is:

1. A cured product obtained through curing of a curable composition for nanoimprinting,
wherein the curable composition for nanoimprinting comprises two or more polymerizable monomers,
the two or more polymerizable monomers include 90 percent by weight or more of two or more monofunctional radically polymerizable monomers,
the two or more monofunctional radically polymerizable monomers give a polymer having a glass transition temperature of 25° C. or higher,
the two or more monofunctional radically polymerizable monomers are at least two compounds selected from the group consisting of (meth)acrylic ester compounds, styrenic compounds, and vinyl ether compounds,
the two or more monofunctional radically polymerizable monomers include at least one radically polymerizable monomer intramolecularly having a cyclic structure as the monofunctional radically polymerizable monomers,
the at least one radically polymerizable monomer intramolecularly having a cyclic structure is at least one compound selected from the group consisting of compounds represented by following Formulae (1) to (3):

wherein R 41 , R 42 , and R 43 are the same as or different from one another and each represent —H or —CH 3 ,
the at least one radically polymerizable monomer intramolecularly having a cyclic structure occupies 40 percent by weight or more of the total weight of the polymerizable monomers in the curable composition,
with the proviso that the at least one radically polymerizable monomer intramolecularly having a cyclic structure includes a compound represented by Formula (1), the compound represented by Formula (1) occupies 40 percent by weight or more of the total weight of the polymerizable monomers, and at least one of the following conditions A, B, and C is met:
[A] the total weight of the compound represented by Formula (1) and the compound represented by Formula (3) occupies 90 percent by weight or more of the total weight of the polymerizable monomers;
[B] the total weight of the compound represented by Formula (1) and (meth)acrylic acid alkyl esters whose alkyl moiety has 1 to 10 carbon atoms occupies 90 percent by weight or more of the total weight of the polymerizable monomers;
[C] the total weight of the compound represented by Formula (1) and/or (3) and phenolic-hydroxyl-containing monofunctional radically polymerizable monomers and/or carboxyl-containing monofunctional radically polymerizable monomers occupies 90 percent by weight or more of the total weight of the polymerizable monomers, and the total weight of the phenolic-hydroxyl-containing monofunctional radically polymerizable monomers and the carboxyl-containing monofunctional radically polymerizable monomers occupies 10 percent by weight or more of the total weight of the polymerizable monomers.

2. The cured product obtained through curing of a curable composition for nanoimprinting according to claim 1 ,
wherein the curable composition further comprises at least one polymer being obtained through polymerization of one or more monofunctional radically polymerizable monomers and having a glass transition temperature of 25° C. or higher.

3. The cured product obtained through curing of a curable composition for nanoimprinting according to claim 1 ,
wherein the curable composition further comprises at least one radical-polymerization initiator.

4. The cured product obtained through curing of a curable composition for nanoimprinting according to claim 1 ,
wherein the at least one radically polymerizable monomer intramolecularly having a cyclic structure includes at least one compound represented by Formula (2) or (3).

5. The cured product obtained through curing of a curable composition for nanoimprinting according to claim 1 ,
wherein one or more monomers selected from the group consisting of phenolic-hydroxyl-containing monofunctional radically polymerizable monomers, carboxyl-containing monofunctional radically polymerizable monomers, and heterocyclic-group-containing monofunctional radically polymerizable monomers occupies 10 percent by weight or more of the total weight of polymerizable monomers in the curable composition.

6. A method for producing a fine structure, comprising nanoimprinting a curable composition for nanoimprinting to give a fine structure,
wherein the curable composition for nanoimprinting comprises two or more polymerizable monomers,
the two or more polymerizable monomers include 90 percent by weight or more of two or more monofunctional radically polymerizable monomers,
the two or more monofunctional radically polymerizable monomers give a polymer having a glass transition temperature of 25° C. or higher,
the two or more monofunctional radically polymerizable monomers are at least two compounds selected from the group consisting of (meth)acrylic ester compounds, styrenic compounds, and vinyl ether compounds,
the two or more monofunctional radically polymerizable monomers include at least one radically polymerizable monomer intramolecularly having a cyclic structure as the monofunctional radically polymerizable monomers,
the at least one radically polymerizable monomer intramolecularly having a cyclic structure is at least one compound selected from the group consisting of compounds represented by following Formulae (1) to (3):

wherein R 41 , R 42 , and R 43 are the same as or different from one another and each represent —H or —CH 3 ,
the at least one radically polymerizable monomer intramolecularly having a cyclic structure occupies 40 percent by weight or more of the total weight of the polymerizable monomers in the curable composition,
with the proviso that the at least one radically polymerizable monomer intramolecularly having a cyclic structure includes a compound represented by Formula (1), the compound represented by Formula (1) occupies 40 percent by weight or more of the total weight of the polymerizable monomers, and at least one of the following conditions A, B, and C is met:
[A] the total weight of the compound represented by Formula (1) and the compound represented by Formula (3) occupies 90 percent by weight or more of the total weight of the polymerizable monomers;
[B] the total weight of the compound represented by Formula (1) and (meth)acrylic acid alkyl esters whose alkyl moiety has 1 to 10 carbon atoms occupies 90 percent by weight or more of the total weight of the polymerizable monomers;
[C] the total weight of the compound represented by Formula (1) and/or (3) and phenolic-hydroxyl-containing monofunctional radically polymerizable monomers and/or carboxyl-containing monofunctional radically polymerizable monomers occupies 90 percent by weight or more of the total weight of the polymerizable monomers, and the total weight of the phenolic-hydroxyl-containing monofunctional radically polymerizable monomers and the carboxyl-containing monofunctional radically polymerizable monomers occupies 10 percent by weight or more of the total weight of the polymerizable monomers.

7. The method for producing a fine structure, according to claim 6 comprising
(1) forming on a substrate a film from the curable composition for nanoimprinting;
(2) stamping an imprint stamp onto the film to transfer a pattern to the film; and
(3) curing the pattern-transferred film to give a fine structure.

8. The method for producing a fine structure, according to claim 7 ,
wherein the imprint stamp used in (2) comprises at least one selected fro

Assignees

• Daicel Corp

Inventors

• Miyake Hiroto
• Yukawa Takao
• Iyoshi Shuso

Classifications

• C08F220/285

  and containing a polyether chain in the alcohol moiety · CPC title

• 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

• C08L33/06

  of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical · CPC title

• G03F7/0002 Primary

  Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title