Curable composition for making cured layer with high thermal stability

Patent metadata

Field	Value
Publication number	US-11434313-B2
Application number	US-202017124063-A
Country	US
Kind code	B2
Filing date	Dec 16, 2020
Priority date	Dec 16, 2020
Publication date	Sep 6, 2022
Grant date	Sep 6, 2022

Abstract

A curable composition can comprise a polymerizable material and a photo-initiator, wherein the polymerizable material can comprise a first monomer including at least one bismaleimide-monomer and at least one second monomer. The curable composition can have a viscosity of not greater than 30 mPa·s, and a cured layer of the curable composition can have a high thermal stability up to 350° C.

First claim

What is claimed is:

1. A curable composition, comprising a polymerizable material and a photoinitiator, wherein
the polymerizable material comprising a first monomer including at least one bismaleimide-monomer and at least one second monomer, wherein the bismaleimide monomer is dissolved within the second monomer;
an amount of the at least one bismaleimide-monomer is at least 5 wt % and not greater than 60 wt % based on the total weight of the polymerizable material;
a viscosity of the curable composition at 23° C. is not greater than 30 mPa·s; and
a cured layer of the curable composition after being subjected to a baking treatment at 350° C. for 30 minutes under nitrogen has a weight loss during a reheating under nitrogen from 25° C. to 350° C. at a rate of 20° C./min of not greater than 2%.

2. The curable composition of claim 1 , wherein the amount of the at least one bismaleimide-monomer is at least 5 wt % and not greater than 30 wt %.

3. The curable composition of claim 2 , wherein the amount of the bismaleimide-monomer is at least 5 wt % and not greater than 15 wt %.

4. The curable composition of claim 1 , wherein the at least one second monomer includes at least one acrylate monomer, divinylbenzene (DVB), N-vinylpyrrolidone (NVP), acryloylmorpholine (AMP), or any combination thereof.

5. The curable composition of claim 4 , wherein the at least one acrylate monomer includes at least one multi-functional acrylate monomer (MFA).

6. The curable composition of claim 4 , wherein the second monomer comprises DVB and at least one multi-functional acrylate monomer.

7. The curable composition of claim 4 , wherein the acrylate monomer comprises a mono-functional acrylate monomer, wherein an amount of the mono-functional acrylate monomer is not greater than 20 wt % based on the total weight of the polymerizable material.

8. The curable composition of claim 1 , wherein the at least one bismaleimide monomer includes 4,4′-bismaleimidodiphenylmethane; bis(3-ethyl-5-methyl-4-maleimidophenyl)methane; 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane or any combination thereof.

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

10. The curable composition of claim 1 , wherein the bismaleimide monomer is a solid at room temperature and dissolved in N-vinylpyrrolidone (NVP) or acryloylmorpholine (AMP).

11. The curable composition of claim 1 , wherein the bismaleimide monomer is a fluid at room temperature and the second monomer comprises DVB, or a multi-functional acrylate monomer, or a combination thereof.

12. A laminate comprising a substrate and a cured layer overlying the substrate, wherein the cured layer is formed from the curable composition of claim 1 .

13. The laminate of claim 12 , wherein the weight loss of the cured layer during the reheating from 25° C. to 350° C. under nitrogen at a speed of 20° C./minute is not greater than 1.5%.

14. A method of forming a cured layer on a substrate, comprising:
applying a layer of a curable composition on the substrate, wherein the curable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprising a first monomer including at least one bismaleimide-monomer and a second monomer, wherein the bismaleimide monomer is dissolved within the second monomer and an amount of the at least one bismaleimide-monomer is at least 5 wt % and not greater than 60 wt % based on the total weight of the polymerizable material;
bringing the curable composition into contact with a superstrate;
irradiating the curable composition with light to form a cured layer; and
removing the superstrate from the cured layer,
wherein the cured layer after being after being subjected to a baking treatment at 350° C. for 30 minutes under nitrogen has a weight loss during a reheating under nitrogen from 25° C. to 350° C. at a rate of 20° C./min of not greater than 2%.

15. The method of claim 14 , wherein a viscosity of the curable composition at 23° C. is not greater than 30 mPa·s.

16. The method of claim 14 , wherein the second monomer includes at least one acrylate monomer, divinylbenzene (DVB), trivinylbenzene (TVB, N-vinylpyrrolidone (NVP), acryloylmorpholine (AMP), or any combination thereof.

17. The method of claim 16 , wherein the acrylate monomer comprises at least one multi-functional acrylate monomer.

18. The method of claim 14 , wherein the at least one bismaleimide monomer includes 4,4′-bismaleimidodiphenylmethane; bis(3-ethyl-5-methyl-4-maleimidophenyl)methane; 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane or any combination thereof.

19. A method of manufacturing an article, comprising:
applying a layer of a curable composition on a substrate, wherein the curable composition comprises a polymerizable material and a photoinitiator, the polymerizable material comprising a first monomer including at least one bismaleimide-monomer and a second monomer, wherein the bismaleimide monomer is dissolved within the second monomer and an amount of the at least one bismaleimide-monomer is at least 5 wt % and not greater than 60 wt % based on the total weight of the polymerizable material;
bringing the curable composition into contact with a superstrate;
irradiating the curable composition with light to form a cured layer;
removing the superstrate from the cured layer, wherein the cured layer after being subjected to a baking treatment at 350° C. for 30 minutes under nitrogen has a weight loss during a reheating under nitrogen from 25° C. to 350° C. at a rate of 20° C./min of not greater than 2%;
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

• Li Fei
• Stachowiak Timothy Brian
• Wan Fen
• Liu Weijun

Classifications

• C08F222/40

  Imides, e.g. cyclic imides · 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

• B32B27/281

  comprising polyimides · CPC title

• C08F226/10

  N-Vinyl-pyrrolidone · CPC title

• C09D125/02

  Homopolymers or copolymers of hydrocarbons · CPC title