Curable composition for photoimprint, cured product, and method of producing film having pattern, optical component, circuit board, or electronic component using the composition

Patent metadata

Field	Value
Publication number	US-10182500-B2
Application number	US-201515121531-A
Country	US
Kind code	B2
Filing date	Feb 10, 2015
Priority date	Feb 26, 2014
Publication date	Jan 15, 2019
Grant date	Jan 15, 2019

Abstract

In an imprint process in a gaseous atmosphere containing a condensable gas, the curable composition for photoimprint is difficult to cure, the pattern is not fully formed to cause defects. The present invention relates to a curable composition for photoimprint in a gaseous atmosphere containing a condensable gas. The curable composition for photoimprint at least comprises the following component (A) and component (B):
(A) polymerizable compound, and (B) photopolymerization initiator.

Component (B) has a saturated solubility of less than 1% by weight in the condensable gas in a liquid state at 5° C. and 1 atm or has a Hansen distance (Ra) of larger than 7.6 to the condensable gas.

First claim

The invention claimed is:

1. A method of producing a film having a pattern, the method comprising:
arranging a curable composition for photoimprint on a substrate;
bringing a mold having a mold pattern for transfer into contact with the curable composition for photoimprint in a gaseous atmosphere containing a condensable gas;
irradiating the curable composition with light to form a cured film; and
releasing the mold from the cured film,
wherein the curable composition for photoimprint is a curable composition for photoimprint in a gaseous atmosphere containing a condensable gas, the curable composition at least comprising component (A) and component (B):
(A) polymerizable compound; and
(B) photopolymerization initiator,
wherein component (B) has a saturated solubility of less than 1% by weight in the condensable gas in a liquid state at 5° C. and 1 atm or has a Hansen distance (Ra) of larger than 7.6 to the condensable gas.

2. The method of producing a film having a pattern according to claim 1 , wherein the gas containing a condensable gas is a gas mixture of a condensable gas and a noncondensable gas.

3. The method of producing a film having a pattern according to claim 2 , wherein the noncondensable gas is an inert gas.

4. The method of producing a film having a pattern according to claim 2 , wherein the noncondensable gas is helium.

5. The method of producing a film having a pattern according to claim 1 , wherein the condensable gas is a chlorofluorocarbon, a fluorocarbon, a hydrochlorofluorocarbon, a hydrofluorocarbon, or a hydrofluoroether.

6. The method of producing a film having a pattern according to claim 1 , wherein the condensable gas is 1,1,1,3,3-pentafluoropropane.

7. The method of producing a film having a pattern according to claim 1 , wherein the condensable gas condenses and liquefies by a pressure of the condensable gas when the curable composition for photoimprint penetrates into a gap between the substrate and the mold or into a concave of the fine pattern on the surface of the mold in the step of bringing the mold into contact with the curable composition.

8. The method of producing a film having a pattern according to claim 1 , wherein the mold pattern of the mold has a quartz surface.

9. A method of producing an optical component, the method comprising:
producing a film having a pattern on a substrate by a method of producing a film according to claim 1 .

10. A method of producing an optical component, the method comprising:
producing a film having a pattern on a substrate by a method of producing a film according to claim 1 ; and
subjecting the substrate to etching or ion implantation using the film having a pattern as a mask.

11. A method of producing a circuit board, the method comprising:
producing a film having a pattern on a substrate by a method of producing a film according to claim 1 ;
subjecting the substrate to etching or ion implantation using the film having a pattern as a mask; and
forming an electronic member.

12. A method of producing an electronic component, the method comprising:
producing a circuit board by the method of producing a circuit board according to claim 11 ; and
connecting the circuit board to a control mechanism for controlling the circuit board.

13. The method of producing a film having a pattern according to claim 1 , wherein component (A) is a (meth)acrylic monomer.

14. The method of producing a film having a pattern according to claim 1 , wherein component (A) includes a monofunctional (meth)acrylic monomer and a polyfunctional (meth)acrylic monomer.

15. The method of producing a film having a pattern according to claim 1 , wherein component (A) has a Hansen distance (Ra) of larger than 4.0 to the condensable gas.

16. The method of producing a film having a pattern according to claim 1 , wherein the gas containing the condensable gas is a gas mixture of a condensable gas and helium.

17. The method of producing a film having a pattern according to claim 1 , wherein the condensable gas is a chlorofluorocarbon, a fluorocarbon, a hydrochlorofluorocarbon, a hydrofluorocarbon, or a hydrofluoroether.

18. The method of producing a film having a pattern according to claim 1 , wherein component (B) is an acylphosphine oxide compound.

19. The method of producing a film having a pattern according to claim 18 , wherein component (B) is represented by Formula (1):

20. The method of producing a film having a pattern according to claim 1 , wherein component (B) is an aminoalkylphenone compound.

21. The method of producing a film having a pattern according to claim 20 , wherein component (B) is represented by Formula (2):

22. The method of producing a film having a pattern according to claim 1 , further comprising component (C):
(C) sensitizer,
wherein component (C) has a Hansen distance (Ra) of larger than 7.6 to the condensable gas.

23. The method of producing a film having a pattern according to claim 22 , wherein component (C) is a benzophenone compound.

24. The method of producing a film having a pattern according to claim 22 , wherein component (C) is represented by Formula (4):

Assignees

• Canon Kk

Inventors

• Honma Takeshi
• Ito Toshiki
• Yonezawa Shiori
• Kawasaki Youji
• Iimura Akiko

Classifications

• C08F220/1811

  C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate · CPC title

• C08F220/1807

  C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title

• B29C59/02

  by mechanical means, e.g. pressing {(B29C59/007 takes precedence; embossing expanded porous articles B29C44/5627)} · CPC title

• B29L2007/008

  Wide strips, e.g. films, webs · CPC title