Adhesion layer composition, method for forming film by nanoimprinting, methods for manufacturing optical component, circuit board and electronic apparatus

Patent metadata

Field	Value
Publication number	US-10073341-B2
Application number	US-201515323939-A
Country	US
Kind code	B2
Filing date	Jun 26, 2015
Priority date	Jul 8, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

In nanoimprinting processes, photo-cured products often separate from the substrate and stick to the mold due to insufficient adhesion between the photo-cured product and the substrate. This causes a defect of pattern separation.
An adhesion layer composition used for forming an adhesion layer between a substrate and a photocurable composition includes a compound (A) having at least two functional groups, and a solvent (B). The functional groups include at least one functional group capable of being bound to the substrate, selected from the group consisting of hydroxy, carboxy, thiol, amino, epoxy, and (blocked) isocyanate, and at least one hydrogen donating group as a functional group capable of being bound to the photocurable composition.

First claim

The invention claimed is:

1. An adhesion layer composition for forming an adhesion layer between a substrate and a photocurable composition, the adhesion layer composition comprising:
a compound (A) containing at least two binding functional groups including at least one functional group directly bound to a hydrocarbon or an aromatic hydrocarbon and capable of being bound to the substrate, and at least one functional group directly bound to a hydrocarbon or an aromatic hydrocarbon and capable of being bound to the photocurable composition; and
a solvent (B),
wherein the functional group capable of being bound to the substrate is at least one selected from the group consisting of hydroxy, carboxy, thiol, amino, epoxy, and (blocked) isocyanate, and the functional group capable of being bound to the photocurable composition is a hydrogen donating functional group, and
wherein the hydrogen donating functional group is thiol or alkylamino.

2. The adhesion layer composition according to claim 1 , wherein the compound (A) contains at least three hydrogen donating functional groups in the molecule thereof.

3. The adhesion layer according to claim 1 , wherein the functional group capable of being bound to the substrate is at least one of hydroxy and thiol.

4. The adhesion layer composition according to claim 1 , wherein the compound (A) has no heterocyclic structure.

5. The adhesion layer composition according to claim 1 , wherein the compound (A) has straight chains extending in four directions, each end of which is bound to the functional group capable of being bound to the substrate or the functional group capable of being bound to the photocurable composition.

6. The adhesion layer composition according to claim 1 , wherein the compound (A) contains at least four thiol groups in the molecule thereof.

7. The adhesion layer composition according to claim 1 , wherein the compound (A) is at least one selected from the group consisting of 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutylate), pentaerythritol tris(3-mercaptobutylate), pentaerythritol tetrakis(3-mercaptopropionate), N-phenylglycine, and N,N,N′,N″,N″-pentakis(2-hydroxypropyl)diethylenetriamine.

8. The adhesion layer composition according to claim 1 , wherein the solvent (B) is propylene glycol monomethyl ether acetate or contains propylene glycol monomethyl ether acetate.

9. The adhesion layer composition according to claim 1 , wherein the photocurable composition contains a polymerizable compound and a photopolymerization initiator.

10. The adhesion layer composition according to claim 9 , wherein the polymerizable compound is (meth)acrylate monomer.

11. A method for forming a photo-cured product pattern, comprising:
forming an adhesion layer by applying the adhesion layer composition as set forth in claim 1 onto a substrate;
applying a photocurable composition to the substrate having the adhesion layer;
bringing the photocurable composition into contact with a mold having an original pattern to be transferred;
irradiating the photocurable composition with light to form a photo-cured product; and
removing the mold from the photo-cured product.

12. The method according to claim 11 , wherein the irradiating is performed using ultraviolet light.

13. The method according to claim 11 , wherein the substrate has a hydroxy group at the surface thereof.

14. The method according to claim 11 , wherein the mold is made of quartz.

15. A method for manufacturing an optical component, the method comprising:
forming a patterned film on a substrate by the method as set forth in claim 11 .

16. A method for manufacturing an optical component, the method comprising:
forming a patterned film by the method as set forth in claim 11 ; and
working the substrate by etching or ion implantation using the patterned film as a mask.

17. A method for manufacturing a circuit board, the method comprising:
forming a patterned film by the method as set forth in claim 11 ;
working the substrate by etching or ion implantation using the patterned film as a mask; and
forming an electronic member.

18. The method according to claim 17 , wherein the circuit board is a semiconductor element.

19. The method for forming a patterned film according to claim 11 , wherein the bringing of the photocurable composition into contact is performed in an atmosphere containing a condensable gas.

20. A method for manufacturing an imprint mold, the method comprising:
forming a photo-cured product pattern on a substrate by the method as set claim 11 ; and
etching the substrate using the photo-cured product pattern.

21. A device component comprising:
a substrate;
a photo-cured product made of a photocurable composition, having a relief pattern on the substrate; and
an adhesion layer between the substrate and the photo-cured product, the adhesion layer containing a compound (A) containing at least two binding functional groups including a functional group capable of being bound to the substrate and a functional group capable of being bound to the photocurable composition,
wherein the functional group capable of being bound to the substrate is bound to a hydrocarbon and selected from the group consisting of hydroxy, carboxy and thiol, and the functional group capable of being bound to the photocurable composition is at least one hydrogen donating functional group bound to a hydrocarbon or an aromatic hydrocarbon, and
wherein the hydrogen donating functional group is thiol or alkylamino.

Assignees

• Canon Kk

Inventors

• Honma Takeshi
• Ito Toshiki
• Otani Tomonori
• Iwashita Kazumi

Classifications

• H10P76/20

  of masks comprising organic materials · CPC title

• H10P50/691

  for Group V materials or Group III-V materials · CPC title

• H10P30/22

  using masks · CPC title

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• B32B2307/75

  Printability · CPC title