Photo-curable composition and methods for preparing cured film, optical component, circuit substrate, electrical component and replica mold using the same

Patent metadata

Field	Value
Publication number	US-11835858-B2
Application number	US-202117320920-A
Country	US
Kind code	B2
Filing date	May 14, 2021
Priority date	Jun 19, 2020
Publication date	Dec 5, 2023
Grant date	Dec 5, 2023

Abstract

An object is to provide a photo-curable composition having high dry etching resistance and high thermal stability. A photo-curable composition includes at least a polymerizable compound (A) and a photopolymerization initiator (B), and further includes at least one of a flame retarder (E) and a flame-retardant polymerizable compound (F).

First claim

What is claimed is:

1. A photo-curable composition comprising at least:
a polymerizable compound (A); and
a photopolymerization initiator (B),
wherein the photo-curable composition further comprises at least one selected from the group consisting of:
a flame retarder (E); and
a flame-retardant polymerizable compound (F),
wherein the photo-curable composition does not include particles larger than 0.2 μm and has a viscosity of 30.0 mPa·s or lower, and
wherein a rate of thermogravimetric decrease is 2.0% or less in a case where the photo-curable composition in a state without a solvent is cured by applying light onto the photo-curable composition in contact with a mold to obtain a cured film, and the cured film is heated at 300° C. for 2 minutes, then cooled to 25° C., and heated from 25° C. to 300° C. under a condition of 20° C./min.

2. The photo-curable composition according to claim 1 , wherein the flame retarder (E) is at least one compound selected from the group consisting of brominated phenyl compounds, condensed phosphate ester compounds, halogen-containing phosphate ester compounds, non-halogen-based aliphatic phosphate ester compounds, non-halogen-based aromatic phosphate ester compounds, and melamine compounds.

3. The photo-curable composition according to claim 1 , wherein the flame retarder (E) is at least one compound selected from the group consisting of pentabromodiphenyl ether, octabromodiphenyl ether, decabromodiphenyl ether, tetrabromobisphenol A, hexabromocyclododecane, hexabromobenzene, resorcinol bis(diphenyl)phosphate, 1,3-phenylene bis(diphenyl phosphate), 1,3-phenylene bis(dixylenyl)phosphate, bisphenol A bis(diphenyl phosphate), phosphonitrilic acid phenyl ester, tris(chloroethyl)phosphate, tris(2,3-dichloropropyl)phosphate, tris(2-chloropropyl)phosphate, tris(2,3-bromopropyl)phosphate, tris(bromochloropropyl)phosphate, 2,3-dibromopropyl-2,3-chloropropyl phosphate, tris(tribromophenyl)phosphate, tris(dibromophenyl)phosphate, tris(tribromoneopentyl)phosphate, trimethyl phosphate, triethyl phosphate, tributyl phosphate, trioctyl phosphate, tributoxyethyl phosphate, triphenyl phosphate, cresyl diphenyl phosphate, dicresyl phenyl phosphate, tricresyl phosphate, trixylenyl phosphate, xylenyl diphenyl phosphate, tris(isopropylphenyl)phosphate, isopropylphenyl diphenyl phosphate, diisopropylphenyl phenyl phosphate, tris(trimethylphenyl)phosphate, tris(t-butylphenyl)phosphate, hydroxyphenyl diphenyl phosphate, octyl diphenyl phosphate, triallyl phosphate, melamine polyphosphate, chlorinated paraffin, polychlorinated biphenyl, melamine cyanurate, tris(2,4-ditertiary butylphenyl)phosphite, 2,6-ditertiary butyl-4-(4,6-bis(octylthio)-1,3,5-triazine-2-ylamino)phenol, and didodecyl-3,3′-thiodipropionate.

4. The photo-curable composition according to claim 1 , wherein the flame-retardant polymerizable compound (F) is a compound containing both a polymerizable functional group and a brominated phenyl group or a phosphate ester group as a flame retardant structure within a single molecule.

5. The photo-curable composition according to claim 1 , wherein a weight of the flame retarder (E) or the flame-retardant polymerizable compound (F) is 1 part by weight to 50 parts by weight when a total of all components excluding a solvent being a component (D) is 100 parts by weight.

6. The photo-curable composition according to claim 1 , wherein a total weight of the flame retarder (E) and the flame-retardant polymerizable compound (F) is 1 part by weight to 50 parts by weight when a total of all components excluding a solvent being a component (D) is 100 parts by weight.

7. The photo-curable composition according to claim 1 , wherein the photo-curable composition contains no solvent.

8. The photo-curable composition according to claim 1 , wherein the photo-curable composition has the viscosity of 30.0 mPa·s or lower when it contains no solvent.

9. The photo-curable composition according to claim 1 , wherein the photo-curable composition has the viscosity of 30.0 mPa·s or lower when it contains a solvent (D) and has the viscosity of 1000.0 mPa·s or lower without the solvent (D).

10. A method for preparing a cured film, comprising:
an arranging step of arranging the photo-curable composition according to claim 1 onto a substrate;
a pressing step of bringing the photo-curable composition and a mold into contact with each other;
a light applying step of applying light onto the photo-curable composition to turn the photo-curable composition into a cured product; and
a releasing step of detaching the cured product and the mold from each other after the light applying step.

11. The method for preparing a cured film according to claim 10 , further comprising:
a heating step of heating the cured product at 250° C. or more for 1 minute or more after the releasing step.

12. A method for preparing a circuit substrate, comprising:
a step of obtaining a cured film with a pattern by performing a lithography step on the cured film prepared by the method according to claim 10 , and performing etching or ion implantation on the substrate by using the cured film with the pattern as a mask; and
a step of removing the cured film with the pattern.

13. The method for preparing a cured film according to claim 10 , wherein a pattern is formed on at least at a portion of a surface of the mold to be brought into contact with the photo-curable composition.

14. A method for preparing an optical component, comprising a step of obtaining a cured film with a pattern by the method for preparing a cured film according to claim 13 .

15. A method for preparing a circuit substrate, comprising:
a step of obtaining a cured film by the method for preparing a cured film according to claim 13 ;
a step of performing etching or ion implantation on the substrate by using the obtained cured product pattern as a mask; and
a step of removing the cured product pattern.

16. The method for preparing a circuit substrate according to claim 12 , wherein the etching is performed using a gas containing at least one of CF 4 , CHF 3 , C 2 F 6 , C 3 F 8 , C 4 F 8 , CCl 2 F 2 , CBrF 3 , and SF 6 .

17. The method for preparing a circuit substrate according to claim 16 , wherein the circuit substrate is a circuit substrate for use in a semiconductor device.

18. A method for preparing a replica mold, comprising the method for preparing a cured film according to claim 13 , wherein the substrate is a quartz substrate.

19. The method for preparing a cured film according to claim 10 , wherein
the substrate has a surface with asperities, and
a surface of the mold has a plane portion at least at a section to be brought into contact with the photo-curable composition.

20. A method for preparing a cured film, comprising, in this order:
an arranging step of arranging droplets of the photo-curable composition according to claim 1 onto a substrate having a surface with asperities by dropping the droplets discretely;
a waiting step of waiting until a surface of a layer of the photo-curable composition becomes plane; and
a light applying step of applying light to cure the layer of the photo-curable composition.

Assignees

• Canon Kk

Inventors

• Ito Toshiki
• Wan Fen

Classifications

• H10P30/22

  using masks · CPC title

• H10P76/2041

  Photolithographic processes · CPC title

• G03F7/027 Primary

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• C09K21/14 Primary

  Macromolecular materials · CPC title

• G03F7/0002

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