Photocurable composition

Patent metadata

Field	Value
Publication number	US-11753497-B2
Application number	US-202117244508-A
Country	US
Kind code	B2
Filing date	Apr 29, 2021
Priority date	Apr 29, 2021
Publication date	Sep 12, 2023
Grant date	Sep 12, 2023

Abstract

In one embodiment, a photocurable composition can comprise a polymerizable material and a photoinitiator, wherein the polymerizable material includes an isocyanate group containing compound of formula (1): R1-R2-N═C═O (1), with R1 including a carbon-carbon double bond, and R2 being substituted or unsubstituted alkyl, aryl, or alkylaryl. An amount of 1 wt % to 10 wt % of the isocyanate group containing compound can cause a strong adhesion strength of the photocurable composition to a silicon substrate after curing, and may allow the omission of an adhesion layer between substrate and the photo-cured layer.

First claim

What is claimed is:

1. A photocurable composition comprising a polymerizable material and a photoinitiator, wherein
the polymerizable material comprises at least one first monomer and at least one second monomer, the at least one first monomer including an isocyanate group containing compound of formula (1): R 1 -R 2 —N═C═O (1), with R 1 including a carbon-carbon double bond, and R 2 being substituted or unsubstituted alkyl, aryl, or alkylaryl;
an amount of the isocyanate group containing compound is between 1 wt % and 10 wt % based on the total weight of the photocurable composition; and
a viscosity of the photocurable composition is not greater than 30 mPa s.

2. The photocurable composition of claim 1 , wherein R 1 of formula (1) is selected from an acrylate group, a methacrylate group or a vinyl group.

3. The photocurable composition of claim 1 , wherein R 2 is phenyl, or C 1 -C 10 alkyl, or C 1 -C 6 alkyl-phenyl.

4. The photocurable composition of claim 1 , wherein the isocyanate group containing compound of formula 1 is selected from 2-isocyanatoethyl acrylate, 3-isopropenyl-α,α-dimethylbenzyl isocyanate, 2-isocyanatoethyl methacrylate, allyl isocyanate, or any combination thereof.

5. The photocurable composition of claim 1 , wherein the isocyanate group containing compound of formula 1 is selected from 2-isocyanatoethyl acrylate or 3-isopropenyl-α,α-dimethylbenzyl isocyanate.

6. The photocurable composition of claim 1 , wherein an amount of the polymerizable material is at least 90 wt % based on a total weight of the photocurable composition.

7. The photocurable composition of claim 1 , wherein the at least one second monomer of the polymerizable material includes an acrylate monomer, a maleimide monomer, an epoxide monomer, a vinylbenzene, or any combination thereof.

8. The photocurable composition of claim 1 , wherein the at least one second monomer includes at least one mono-functional acrylate monomer and at least one multi-functional acrylate monomer.

9. The photocurable composition of claim 8 , wherein an amount of the multi-functional acrylate monomer is at least 20 wt % based on the total weight of the curable composition.

10. The photocurable composition of claim 8 , wherein an amount of the multi-functional acrylate monomer is at least 40 wt % based on the total weight of the curable composition.

11. The photocurable composition of claim 1 , wherein the viscosity of the curable composition at 23° C. is not greater than 15 mPa·s.

12. The photocurable composition of claim 1 , wherein the curable composition is essentially free of a solvent.

13. A laminate comprising a substrate and a photo-cured layer directly overlying the substrate, wherein the photo-cured layer is formed from the photocurable composition of claim 1 .

14. The laminate of claim 13 , wherein an adhesion strength of the photo-cured layer to a silicon substrate at 23° C. according to ASTM D 4541 is at least 6.5 MPa.

15. A method of forming a photo-cured layer on a substrate, comprising:
applying a layer of a photocurable composition directly on the substrate, wherein the photocurable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprising at least one first monomer and at least one second monomer, the at least one first monomer including 1 wt % to 10 wt % of an isocyanate group containing compound of formula (1): R 1 -R 2 —N═C═O (1), with R 1 including a carbon-carbon double bond, and R 2 being substituted or unsubstituted alkyl or aryl, and a viscosity of the photocurable composition is not greater than 30 mPa·s;
bringing the photocurable composition into contact with an imprint template or a superstrate;
irradiating the photocurable composition with light to form a photo-cured layer; and
removing the imprint template or superstrate from the photo-cured layer.

16. The method of claim 15 , wherein the isocyanate group containing compound of formula (1) is selected from 2-isocyanatoethyl acrylate, 3-isopropenyl-α,α-dimethylbenzyl isocyanate, 2-isocyanatoethyl methacrylate, allyl isocyanate, or any combination thereof.

17. The method of claim 15 , wherein the at least one second monomer of the polymerizable material includes at least one mono-functional acrylate monomer and at least one multi-functional acrylate monomer.

18. The method of claim 15 , wherein an amount of the polymerizable material is at least 90 wt % based on a total weight of the curable composition.

19. A method of manufacturing an article, comprising:
applying a layer of a photocurable composition on a substrate, wherein the photocurable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprising at least one first monomer and at least one second monomer, the at least one first monomer including 1 wt % to 10 wt % of an isocyanate group containing compound of formula (1): R 1 -R 2 —N═C═O (1), with R 1 including a carbon-carbon double bond, and R 2 being substituted or unsubstituted alkyl or aryl, and a viscosity of the photocurable composition is not greater than 30 mPa·s;
bringing the photocurable composition into contact with an imprint template or a superstrate;
irradiating the photocurable composition with light to form an at least partially photo-cured layer;
removing the imprint template or the superstrate from the at least partially photo-cured layer;
forming a pattern on the substrate;
processing the substrate on which the pattern has been formed in the forming; and
manufacturing an article from the substrate processed in the processing.

Assignees

• Canon Kk

Inventors

• Wan Fen
• Liu Weijun

Classifications

• C08G18/8116 Primary

  esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group · CPC title

• C08G18/711 Primary

  containing oxygen in addition to isocyanate oxygen · CPC title

• C08G18/8108

  having only one isocyanate or isothiocyanate group · CPC title

• C08G18/712

  containing halogens · CPC title

• C08G18/714

  containing nitrogen in addition to isocyanate or isothiocyanate nitrogen · CPC title