Photocurable composition with enhanced thermal stability

Patent metadata

Field	Value
Publication number	US-11945966-B2
Application number	US-202117643534-A
Country	US
Kind code	B2
Filing date	Dec 9, 2021
Priority date	Dec 9, 2021
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

A photocurable composition can comprise a polymerizable material and a photoinitiator, wherein the polymerizable material may comprise at least one first polymerizable monomer having a structure of Formula (1): (R 1 ) x —Ar—(R 2 ) y (1), with Ar being one or more substituted or unsubstituted aromatic rings; R 1 being a structure covalently bonded to Ar including at least one acrylate group; x being 1-4; and R 2 being —CH═CH 2 or —CCH 3 =CH 2 covalently bonded to Ar; y being 1-4.

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 polymerizable monomer having a structure of formula (1): (R 1 ) x —Ar—(R 2 ) y (1), with
Ar being one or more substituted or unsubstituted aromatic rings;
R 1 being a structure covalently bonded to Ar including at least one acrylate group; x being 1-4;
R 2 being —CH═CH 2 or —CCH 3 ═CH 2 covalently bonded to Ar; y being 1-4,

and wherein an amount of the at least one first polymerizable monomer is in a range from 50 wt % to 100 wt % based on the total weight of the polymerizable material.

2. The photocurable composition of claim 1 , wherein Ar is selected from benzene, phenylbenzene, or naphthalene.

3. The photocurable composition of claim 2 , wherein the at least one first polymerizable monomer comprises a structure of formula (2) or formula (3):

with R 3 being C1-C5 alkyl or oxyalkyl, x being 1-4; R 4 being hydrogen or C1-C4 alkyl;
y being 1-4, and z being 1-3.

4. The photocurable composition of claim 3 , wherein the at least one first polymerizable monomer comprises at least one of the following structures:

5. The photocurable composition of claim 1 , wherein the at least one first polymerizable monomer has a vapor pressure not greater than 0.01 mmHg at 25° C.

6. The photocurable composition of claim 5 A photocurable composition comprising a polymerizable material and a photoinitiator, wherein the polymerizable material comprises at least one first polymerizable monomer having a structure of formula (1): (R 1 ) x —Ar—(R 2 ) y (1), with
Ar being one or more substituted or unsubstituted aromatic rings;
R 1 being a structure covalently bonded to Ar including at least one acrylate group; x being 1-4;
R 2 being —CH═CH 2 or —CCH 3 ═CH 2 covalently bonded to Ar;
y being 1-4,

wherein the at least one first polymerizable monomer has a vapor pressure not greater than 0.001 mmHg at 25° C.

7. The photocurable composition of claim 1 , wherein the polymerizable material further comprises at least one second polymerizable monomer having a different structure than Formula I.

8. The photocurable composition of claim 7 , wherein the at least one second polymerizable monomer includes at least one mono-functional acrylate monomer.

9. The photocurable composition of claim 7 , wherein the at least one second polymerizable monomer comprises at least one mono-functional monomer and at least one multi-functional monomer.

10. The photocurable composition of claim 1 , wherein an amount of the polymerizable material is at least 80 wt % based on the total weight of the photocurable composition.

11. The photocurable composition of claim 1 , wherein a viscosity at 23° C. of the photocurable composition is not greater than 50 mPa s.

12. The photocurable composition of claim 1 , wherein the photocurable composition comprises a solvent in an amount of at least 15 vol % based on the total volume of the photocurable composition.

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

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

15. The laminate of claim 14 , wherein the photo-cured layer has an Ohnishi number of not greater than 3.2.

16. The laminate of claim 14 , wherein the photo-cured layer has degradation temperature of at least 300° C.

17. A method of forming a photo-cured layer on a substrate, comprising:
applying a layer of a photocurable composition on the substrate, wherein the photocurable composition comprises a photoinitiator and a polymerizable material, the polymerizable material comprising at least one first polymerizable monomer having a structure of formula (1): (R 1 ) x —Ar—(R 2 ) y (1), with Ar being one or more substituted or unsubstituted aromatic rings; R 1 being a structure covalently bonded to Ar including at least one acrylate group; x being 1-4; R 2 being —CH═CH2 or —CCH 3 ═CH 2 covalently bonded to Ar; y being 1-4, and wherein an amount of the at least one first polymerizable monomer is in a range from 50 wt % to 100 wt % based on the total weight of the polymerizable material;
bringing the photocurable composition into contact with a template or a superstrate;
irradiating the photocurable composition with light to form a photo-cured layer; and
removing the template or the superstrate from the photo-cured layer.

18. The method of claim 17 , wherein the cross-linking agent comprises a structure of formula (2) or formula (3):

with R 3 being C 1 -C 5 being alkyl or oxyalkyl, x being 1-4; R 4 being hydrogen or C1-C4 alkyl, y being 1-4, and z being 1-3.

19. A method of manufacturing an article, comprising forming a photo-cured layer on a substrate according to claim 17 , and further comprising:
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

• C09D135/02

  Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence) · CPC title

• C09D133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C09D4/00 Primary

  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

• C08F2/50

  with sensitising agents · CPC title

• C08F212/34

  Monomers containing two or more unsaturated aliphatic radicals · CPC title