Curable composition for imprints, patterning method and pattern

Patent metadata

Field	Value
Publication number	US-9868846-B2
Application number	US-201414151367-A
Country	US
Kind code	B2
Filing date	Jan 9, 2014
Priority date	Jul 12, 2011
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

Disclosed is a to provide a curable composition for imprints capable of keeping a good patternability and of producing less defects even after repetitive pattern transfer. The curable composition for imprints comprising: a polymerizable compound (A);
a photo-polymerization initiator (B); and a non-polymerizable compound (C) having a polyalkylene glycol structure having at least one terminal hydroxy group, or at least one etherified terminal hydroxy group, and containing substantially no fluorine atom and no silicon atom.

First claim

The invention claimed is:

1. A curable composition for imprints comprising:
a polymerizable compound (A) which contains a compound having aromatic group(s) and/or alicyclic hydrocarbon group(s);
a photo-polymerization initiator (B); and
a non-polymerizable compound (C) having a weight average molecular weight of 150 to 10,000 and having a polyalkylene glycol structure having at least one terminal hydroxy group, or at least one etherified terminal hydroxy group, and containing substantially no fluorine atom and no silicon atom,
wherein the non-polymerizable compound (C) contains at least one species selected from the group consisting of polyalkylene glycol, polyalkylene glycol ether and polyalkylene glycol ester, and
the content of constituents other than the polyalkylene glycol structure in the non-polymerizable compound (C) is 5% by mass or less.

2. The curable composition for imprints of claim 1 ,
containing a (meth)acrylate compound, as the polymerizable compound (A).

3. The curable composition for imprints of claim 1 ,
wherein the polymerizable compound (A) contains a compound having fluorine atom(s) and/or silicon atom(s).

4. The curable composition for imprints of claim 1 ,
containing polypropylene glycol, as the non-polymerizable compound (C).

5. The curable composition for imprints of claim 1 ,
containing substantially no solvent.

6. The curable composition for imprints of claim 1 ,
further containing a surfactant.

7. The curable composition for imprints of claim 1 ,
designed for inkjet process.

8. The curable composition for imprints of claim 1 , wherein the polyalkylene glycol structure is a straight chain structure of polyalkylene glycol and the non-polymerizable compound (C) has hydroxyl groups at both terminals of the straight chain structure of polyalkylene glycol.

9. The curable composition for imprints of claim 1 ,
containing a (meth)acrylate compound having fluorine atom(s) and/or silicon atom(s), as the polymerizable compound (A).

10. The curable composition for imprints of claim 1 ,
containing a combination of a (meth)acrylate compound having aromatic group(s) and/or alicyclic hydrocarbon group(s), and a (meth)acrylate compound having fluorine atom(s) and/or silicon atom(s), as the polymerizable compound (A).

11. The curable composition for imprints of claim 1 ,
containing a combination of a (meth)acrylate compound having aromatic group(s) and/or alicyclic hydrocarbon group(s), and a (meth)acrylate compound having fluorine atom(s) and/or silicon atom(s), as the polymerizable compound (A); and polypropylene glycol, as the non-polymerizable compound (C).

12. The curable composition for imprints of claim 1 ,
containing a combination of a (meth)acrylate compound having aromatic group(s) and/or alicyclic hydrocarbon group(s), and a (meth)acrylate compound having fluorine atom(s) and/or silicon atom(s), as the polymerizable compound (A); and a diol type polyalkylene glycol, as the non-polymerizable compound (C).

13. A method of forming a pattern, the method comprising applying the curable composition for imprints described in claim 1 on a base, or on a mold having a fine pattern formed thereon, pressing the mold or the base against the curable composition for imprints, and irradiating the curable composition for imprints with light.

14. The method of forming a pattern of claim 13 , wherein the curable composition for imprints is applied on the base, or on the mold by an inkjet method.

15. A pattern obtained by the method described in claim 13 .

16. An electronic device comprising the pattern described in claim 15 .

17. A method of manufacturing an electronic device comprising the method of forming a pattern described in claim 13 .

18. A curable composition for imprints comprising:
a polymerizable compound (A);
a photo-polymerization initiator (B);
a non-polymerizable compound (C) having a polyalkylene glycol structure having at least one terminal hydroxy group, or at least one etherified terminal hydroxy group, and containing substantially no fluorine atom and no silicon atom; and
a polymerization inhibitor;
wherein the content of constituents other than the polyalkylene glycol structure in the non-polymerizable compound (C) is 5% by mass or less, and
the polymerization inhibitor is selected from the group consisting of hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4′-thiobis (3-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-methyl-6-tert-butylphenol), cerium (III) salt of N-nitrosophenyl hydroxylamine, phenothiazine, phenoxazine, 4-methoxynaphthol, 2,2,6,6-tetramethylpiperidine-1-oxyl, 2,2,6,6-tetramethylpiperidine, 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, nitrobenzene, and dimethylaniline.

19. The curable composition for imprints of claim 1 , wherein the non-polymerizable compound (C) is selected from the group consisting of:
polyethylene glycol,
polypropylene glycol,
mono- or dimethyl ether, mono- or dioctyl ether, mono- or dinonyl ether, mono- or didecyl ether, monostearate, monooleate, monoadipate, or monosuccinate of polyethylene glycol, and
mono- or dimethyl ether, mono- or dioctyl ether, mono- or dinonyl ether, mono- or didecyl ether, monostearate, monooleate, monoadipate, or monosuccinate of polypropylene glycol.

20. The curable composition for imprints of claim 18 , wherein the non-polymerizable compound (C) is selected from the group consisting of:
polyethylene glycol,
polypropylene glycol,
mono- or dimethyl ether, mono- or dioctyl ether, mono- or dinonyl ether, mono- or didecyl ether, monostearate, monooleate, monoadipate, or monosuccinate of polyethylene glycol, and
mono- or dimethyl ether, mono- or dioctyl ether, mono- or dinonyl ether, mono- or didecyl ether, monostearate, monooleate, monoadipate, or monosuccinate of polypropylene glycol.

Assignees

• Fujifilm Corp

Inventors

• Kodama Kunihiko
• Enomoto Yuichiro
• Usuki Kazuyuki
• Omatsu Tadashi
• Kitagawa Hirotaka

Classifications

• C08F220/10

  Esters · CPC title

• Y10T428/24479

  including variation in thickness · CPC title

• G11B5/855 Primary

  Coating only part of a support with a magnetic layer · CPC title

• C08F220/22

  Esters containing halogen · CPC title

• C08F220/382

  and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate · CPC title