IP Library Granted Patent US 11,945,893
Granted Patent B2
US 11,945,893 · App. 17/038,491 · Granted Apr 2, 2024

Curable composition

Inventors: Fen Wan (Austin, TX); Weijun Liu (Cedar Park, TX); Gary F. Doyle (Round Rock, TX)
Assignee: CANON KABUSHIKI KAISHA
C08F222/10C08F2/50C08F220/1807C08F220/1811C08F236/20C08F236/22G03F7/0005B82Y40/00
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Quick Facts
Patent No.
US 11,945,893
App. No.
17/038,491
Granted
Apr 2, 2024
Kind
B2
Abstract

A curable composition can comprise a polymerizable material including a monomer of Formula (1), with R being H or alkyl or alkylaryl, n being 1-4, m being 0-6, X 1 being C 1 -C 6 substituted or unsubstituted alkyl, X 2 being CH 3 or H, After forming a cured layer of the curable composition, the cured layer can have an excellent etch resistance.

Claims (35)

1. A curable composition comprising:

a polymerizable material consisting essentially of a monomer of Formula (1):

wherein R is H or alkyl or alkylaryl, n being 1-4, m is 0-6, X 1 is C 1 -C 6 alkyl, X 2 is CH 3 or H; and

at least one second acrylate monomer different from the monomer of Formula (1),

wherein

an amount of the monomer of Formula (1) is at least 5 wt % and not greater than 30 wt % based on the total weight of the curable composition;

an amount of the at least one second monomer is at least 50 wt % based on the total weight of the curable composition; and

a viscosity of the curable composition is not greater than 20 mPa s.

2. The curable composition of claim 1 , wherein the monomer of Formula (1) includes a di-functional acrylate monomer.

3. The curable composition of claim 2 , wherein the di-functional acrylate monomer includes a structure of Formula (2):

4. The curable composition of claim 1 , wherein an amount of the polymerizable material is at least 80 wt % and not greater than 98 wt % based on the total weight of the curable composition.

5. The curable composition of claim 1 , wherein the at least one second acrylate monomer is selected from the group consisting of benzyl acrylate (BA), or isobornyl acrylate (IBOA), or neopentyl glycol diacrylate (A-NPG), and any combination thereof.

6. The curable composition of claim 1 , wherein the composition has a viscosity not greater than 15 mPa s.

7. The curable composition of claim 1 , further comprising a photo-initiator.

8. The curable composition of claim 1 , wherein the curable composition is adapted for use as a resist in a nanoimprint lithographic process.

9. The curable composition of claim 1 , wherein an Ohnishi number of the curable composition after curing is not greater than 3.6.

10. 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 .

11. The laminate of claim 10 , wherein the cured layer has an Ohnishi number of not greater than 3.6.

12. A method of forming a cured layer on a substrate, comprising:

applying a curable composition on a substrate, wherein the curable composition comprises a polymerizable material including a monomer having a structure of Formula (1):

wherein R is H or alkyl or alkylaryl, n is 1-4, m is 0-6, X 1 is C 1 -C 6 alkyl, X 2 is CH 3 or H; and at least one second acrylate monomer different from the monomer of Formula (1), wherein an amount of the monomer of Formula (1) is at least 5 wt % and not greater than 30 wt % based on the total weight of the curable composition, an amount of the at least one second monomer is at least 50 wt % based on the total weight of the curable composition, and a viscosity of the curable composition is not greater than 20 mPa s;

bringing the curable composition into contact with a superstrate;

curing the curable composition with light and/or heat to form a cured layer; and

removing the superstrate from the cured layer.

13. The method of claim 12 , wherein a viscosity of the curable composition is not greater than 15 mPa s.

14. The method of claim 12 , wherein the monomer of Formula (1) includes a structure of Formula (2)

15. A method of manufacturing an article, comprising:

applying a curable composition on a substrate, wherein the curable composition comprises a polymerizable material including a monomer having a structure of Formula (1):

wherein R is H or alkyl or alkylaryl, n is 1-4, m is 0-6, X 1 is C 1 -C 6 alkyl, X 2 is CH 3 or H; and at least one second acrylate monomer different from the monomer of Formula (1), wherein an amount of the monomer of Formula (1) is at least 5 wt % and not greater than 30 wt % based on the total weight of the curable composition, an amount of the at least one second monomer is at least 50 wt % based on the total weight of the curable composition, and a viscosity of the curable composition is not greater than 20 mPa s;

bringing the curable composition into contact with a superstrate;

curing the curable composition with light and/or heat to form a cured layer; and

removing the superstrate from the cured layer;

removing the superstrate from the photo-cured layer; and

processing the substrate with the photo-cured layer to make the article.

16. The method of claim 15 , wherein the viscosity of the curable composition is not greater than 15 mPa·s.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2021
From: WAN, FEN; LIU, WEIJUN; DOYLE, GARY F.
To: CANON KABUSHIKI KAISHA
Reel/Frame 055114/0691 →
Continuity (1)
Related Publication 20220098345A1 · Mar 31, 2022