IP Library Granted Patent US 7,837,921
Granted Patent B2
US 7,837,921 · App. 11/244,428 · Granted Nov 23, 2010

Method of providing desirable wetting and release characteristics between a mold and a polymerizable composition

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Quick Facts
Patent No.
US 7,837,921
App. No.
11/244,428
Granted
Nov 23, 2010
Kind
B2
Abstract

The present invention provides a method that features improved wetting characteristics while allowing preferential adhesion and release characteristics with respect to a substrate and a mold having imprinting material disposed therebetween. The method includes coating a surface of the mold with a volume of surfactant containing solution. The surfactant in the solution includes a hydrophobic component consisting essentially of a plurality of fluorine-containing molecules. The distribution of the plurality of the fluorine atoms in the fluorine-containing molecules, as well as the fluorine-containing molecules throughout the volume provides a desired contact angle with respect to a polymerizable composition disposed on the substrate. The contact angle is in a range of 50° or less.

Claims (50)

1. A method of providing desirable wetting and release characteristics between a mold, having a surface, and a polymerizable composition, the method comprising:

coating the surface of the mold with a volume of surfactant-containing solution, with the surfactant including a fluorinated hydrophobic component providing a contact angle with a magnitude that is less than about 20° with respect to the polymerizable composition.

2. The method as recited in claim 1 wherein the surfactant-containing solution and the polymerizable composition are formed from the same constituent components.

3. The method as recited in claim 1 wherein the surfactant-containing solution the polymerizable composition are formed from differing constituent components.

4. The method as recited in claim 1 wherein the fluorinated hydrophobic component comprises CF 3 and CF 2 groups.

5. The method of claim 1 further comprising forming, adjacent to the surface of the mold, a layer of the polymerizable composition having a surfactant-rich region and a surfactant-depleted region, with the surfactant-rich region having a desired thickness.

6. The method as recited in claim 5 wherein the desired thickness of the surfactant-rich region is approximately 1 nm.

7. The method as recited in claim 5 wherein the surfactant-rich region includes fluorine-containing molecules selected from a set of fluorine-containing molecules consisting essentially of CF 3 and CF 2 groups.

8. A method of providing desirable wetting and release characteristics between a mold, having a surface, and a polymerizable composition, the method comprising:

disposing a layer of a surfactant-containing solution on the surface of the mold;

depositing the polymerizable composition on a substrate; and

contacting the polymerizable composition with the surfactant-containing solution layer on the surface of the mold, defining an interface, with the surfactant-containing solution layer and the polymerizable composition each including a surfactant component, with an aggregate quantity of the surfactant component at the interface being sufficient to generate a lamella layer,

wherein a contact angle of the polymerizable composition on the surface of the mold is less than about 20°.

9. The method as recited in claim 8 wherein a thickness of the lamella layer is approximately 1 nm.

10. The method as recited in claim 8 wherein the fluorine-containing molecules are selected from a set of fluorine-containing molecules consisting essentially of CF 3 and CF 2 groups.

11. A method of imprint lithography, the method comprising:

depositing an imprinting material on a substrate;

varying release properties associated with an imprint template by contacting a solution including imprinting materials and a polymeric fluorinated surfactant with the imprint template, wherein the polymeric fluorinated surfactant comprises a non-ionic acrylic copolymer based fluorochemical surfactant that comprises perfluorobutane sulfonate segments; and

energizing the imprinting materials to cause a solid material to be produced therefrom.

12. The method of claim 11 further comprising pre-treating the surface of the imprint template to be hydrophilic.

13. The method of claim 11 further comprising pre-treating the surface of the imprint template by applying a composition that includes the surfactant to the surface of the imprint template.

14. The method of claim 13 wherein the composition that includes the surfactant is a mixture of isopropyl alcohol and the surfactant.

15. A method of imprint lithography, the method comprising:

depositing an imprinting material on a substrate;

moving an imprint template towards the substrate so that the imprinting material coats a surface of the imprint template and a surface of the substrate; and

energizing the imprinting material to cause a solid material to be produced therefrom,

wherein the imprinting material includes a surfactant having a composition that includes 87% polymeric fluorochemical actives, 7% non-fluorochemical actives, 5% 1-methyl-2-pyrrolidinone, and less than 1% toluene.

16. The method of claim 11 wherein the imprinting material includes acryloxymethylpentamethyldisiloxane, isobornyl acrylate, ethylene glycol diacrylate, and 2-hydrozy-2 methyl-1-phenyl-propan-1-one.

17. The method of claim 15 wherein the imprinting material includes acryloxymethylpentamethyldisiloxane, isobornyl acrylate, ethylene glycol diacrylate, and 2-hydrozy-2 methyl-1-phenyl-propan-1-one.

18. The method of claim 16 wherein the surfactant is less than 1% of the imprinting material.

19. The method of claim 17 wherein the surfactant is less than 1% of the imprinting material.

20. The method of claim 15 wherein depositing the imprinting material on the substrate includes depositing a plurality of droplets upon the substrate.

21. The method of claim 15 wherein depositing the imprinting material on the substrate includes spin-coating the imprinting material on the substrate.

22. The method of claim 15 further comprising pre-treating the surface of the imprint template to be hydrophilic.

23. The method of claim 22 wherein pre-treating includes hydrolyzing the surface of the imprint template.

24. The method of claim 23 wherein hydrolyzing includes forming —OH bonds at the surface of the imprint template.

25. A method of imprint lithography, the method comprising:

pre-treating a surface of an imprint template to cause it to be hydrophilic;

pre-treating the surface of the imprint template, without forming an a priori release layer, by applying a composition comprising a non-ionic acrylic copolymer based fluorochemical surfactant to the surface of the template, wherein the surfactant comprises perfluorobutane sulfonate segments;

depositing an imprinting material on a substrate;

moving the imprint template towards the substrate so that the imprinting material coats the surface of the imprint template and a surface of the substrate; and

energizing the imprinting material to cause a solid material to be produced therefrom.

26. An imprinting material for use in imprint lithography, the imprinting material comprising a polymeric fluorinated surfactant, wherein the polymeric fluorinated surfactant comprises a non-ionic acrylic copolymer based fluorochemical surfactant that comprises perfluorobutane sulfonate segments.

27. The imprinting material of claim 26 further comprising a UV photoinitiator.

28. The imprinting material of claim 27 further comprising acryloxymethylpentamethyldisiloxane, isobornyl acrylate, ethylene glycol diacrylate, and 2-hydroxy-2-methyl-1-phenyl-propan-1-one.

29. The imprinting material of claim 26 wherein the non-ionic acrylic copolymer based fluorochemical surfactant comprises less than about 1% of the imprinting material.

30. A method of providing desirable wetting and release characteristics between a surface of a nanoimprint lithography mold and a polymerizable composition, the method comprising:

coating the surface of the mold with a volume of surfactant-containing solution, the surfactant including a fluorinated hydrophobic component providing a contact angle with a magnitude that is about 26.5° or less with respect to the polymerizable composition.

31. The method of claim 30 , wherein the surfactant-containing solution and the polymerizable composition are substantially the same.

32. The method of claim 30 , wherein the surfactant-containing solution and the polymerizable composition are substantially the same, and coating the surface of the mold with the volume of surfactant-containing solution comprises contacting the surface of the mold with the polymerizable composition.

Assignments (10)
ASSIGNMENT OF SECURITY INTEREST IN PATENTS Recorded Nov 7, 2019
From: JPMORGAN CHASE BANK, N.A.
To: CITIBANK, N.A.
Reel/Frame 050967/0138 →
PATENT SECURITY AGREEMENT Recorded Aug 22, 2019
From: MAGIC LEAP, INC.; MOLECULAR IMPRINTS, INC.; MENTOR ACQUISITION ONE, LLC
To: JP MORGAN CHASE BANK, N.A.
Reel/Frame 050138/0287 →
CONFIRMATORY ASSIGNMENT OF JOINT PATENT OWNERSHIP Recorded Apr 27, 2015
From: CANON NANOTECHNOLOGIES, INC.
To: MOLECULAR IMPRINTS, INC.
Reel/Frame 035507/0559 →
CHANGE OF NAME Recorded Jul 30, 2014
From: MII NEWCO, INC.
To: MOLECULAR IMPRINTS, INC.
Reel/Frame 033449/0684 →
CHANGE OF NAME Recorded Jul 24, 2014
From: MOLECULAR IMPRINTS, INC.
To: CANON NANOTECHNOLOGIES, INC.
Reel/Frame 033400/0184 →
ASSIGNMENT OF JOINT OWNERSHIP Recorded Jul 15, 2014
From: MOLECULAR IMPRINTS, INC.
To: MII NEWCO, INC.
Reel/Frame 033329/0280 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR AND ASSIGNEE PREVIOUSLY RECORDED ON REEL 033161 FRAME 0705. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 25, 2014
From: CANON INC.
To: MOLECULAR IMPRINTS, INC.
Reel/Frame 033227/0398 →
RELEASE OF SECURITY INTEREST Recorded Jun 13, 2014
From: MOLECULAR IMPRINTS, INC.
To: CANON INC.
Reel/Frame 033161/0705 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE FROM AN "ASSIGNMENT" TO "SECURITY AGREEMENT" PREVIOUSLY RECORDED ON REEL 026842 FRAME 0929. ASSIGNOR(S) HEREBY CONFIRMS THE THE ORIGINAL DOCUMENT SUBMITTED WAS A "SECURITY AGREEMENT". Recorded Aug 13, 2013
From: MOLECULAR IMPRINTS, INC.
To: CANON INC.
Reel/Frame 031003/0031 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 1, 2011
From: MOLECULAR IMPRINTS, INC.
To: CANON INC.
Reel/Frame 026842/0929 →