Curable composition for imprinting, cured product, pattern forming method, lithography method, pattern, mask for lithography, and polymerizable composition for imprinting

Patent metadata

Field	Value
Publication number	US-11401361-B2
Application number	US-202016750585-A
Country	US
Kind code	B2
Filing date	Jan 23, 2020
Priority date	Jul 26, 2017
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

The curable composition for imprinting includes: a compound represented by the following Formula (1); a radically polymerizable compound other than the compound represented by Formula (1); and a photoradical polymerization initiator, in Formula (1), R 1 and R 2 each independently represent a hydrogen atom or an organic group having 1 to 8 carbon atoms and may be bonded to each other to form a ring, R 3 represents a monovalent organic group, and R 4 and R 5 each independently represent a hydrogen atom or a monovalent organic group.

First claim

What is claimed is:

1. A curable composition for imprinting comprising:
a compound represented by the following Formula (1);
a radically polymerizable compound other than the compound represented by Formula (1); and
a photoradical polymerization initiator,

in Formula (1), R 1 and R 2 each independently represents a hydrogen atom or an organic group having 1 to 8 carbon atoms and may be bonded to each other to form a ring, R 3 represents a monovalent organic group, and R 4 and R 5 each independently represents a hydrogen atom or a monovalent organic group, provided that either R 4 or R 5 in Formula (1) is represented by the following Formula (1-3),

in Formula (1-3), R 6 represents a monovalent organic group and * represents a binding site.

2. The curable composition for imprinting according to claim 1 ,
wherein the content of the compound represented by Formula (1) is 0.005 to 1 part by mass with respect to 100 parts by mass of the radically polymerizable compound other than the compound represented by Formula (1).

3. The curable composition for imprinting according to claim 1 ,
wherein the radically polymerizable compound other than the compound represented by Formula (1) includes at least one (meth)acryloyl group.

4. The curable composition for imprinting according to claim 1 ,
wherein the molecular weight of the compound represented by Formula (1) is 100 to 1500.

5. The curable composition for imprinting according to claim 1 ,
wherein the compound represented by Formula (1) has a radically polymerizable group.

6. The curable composition for imprinting according to claim 1 ,
wherein R 3 in Formula (1) and R 6 in Formula (1-3) are each independently represented by the following Formula (1-1),

in the formula, R 7 represents a divalent organic group, R C represents a hydrogen atom or a methyl group, and * represents a binding site.

7. The curable composition for imprinting according to claim 1 ,
wherein at least one radically polymerizable compound other than the compound represented by Formula (1) includes a compound represented by the following Formula (2),

in Formula (2), R 21 represents a q-valent organic group, R 22 represents a hydrogen atom or a methyl group, and q represents an integer of 2 or more.

8. The curable composition for imprinting according to claim 1 ,
wherein at least one radically polymerizable compound other than the compound represented by Formula (1) is a monofunctional (meth)acrylic monomer.

9. The curable composition for imprinting according to claim 1 ,
wherein a content of a solvent in the curable composition for imprinting is 5 mass % or lower.

10. The curable composition for imprinting according to claim 1 ,
wherein a content of a component having a weight-average molecular weight of higher than 2000 in the curable composition for imprinting is 5 mass % or lower.

11. The curable composition for imprinting according to claim 1 ,
wherein the viscosity of the curable composition for imprinting at 25° C. is 3 to 15 mPa·s.

12. A cured product which is formed of the curable composition for imprinting according to claim 1 .

13. The cured product according to claim 12 , which is provided on a silicon substrate.

14. A patterned cured product forming method comprising:
applying the curable composition for imprinting according to claim 1 to a substrate or a mold with a pattern; and
forming the patterned cured product by irradiating the curable composition for imprinting with light in a state where the curable composition for imprinting is interposed between the mold and the substrate.

15. The patterned cured product forming method according to claim 14 ,
wherein the size of the pattern of the obtained patterned cured product is 30 nm or less.

16. A method of manufacturing a substrate to be processed comprising:
performing etching by using a patterned cured product which is obtained using the patterned cured product forming method according to claim 14 as a mask.

17. A patterned cured product which is formed of the curable composition according to claim 1 ,
wherein the size of the patterned cured product is 30 nm or less.

18. A mask for etching comprising:
at least one patterned cured product according to claim 17 .

19. A polymerizable composition for imprinting comprising:
a compound represented by the following Formula (1); and
a compound represented by the following Formula (2),

in Formula (1), R 1 and R 2 each independently represents a hydrogen atom or an organic group having 1 to 8 carbon atoms and may be bonded to each other to form a ring, R 3 represents a monovalent organic group, and R 4 and R 5 each independently represents a hydrogen atom or a monovalent organic group, provided that either R 4 or R 5 in Formula (1) is represented by the following Formula (1-3),

in Formula (1-3), R 6 represents a monovalent organic group and * represents a binding site, and

in Formula (2), R 21 represents a q-valent organic group, R 22 represents a hydrogen atom or a methyl group, and q represents an integer of 2 or more.

Assignees

• Fujifilm Corp

Inventors

• Shimoju Naoya
• Shibuya Akinori
• Goto Yuichiro

Classifications

• H10P76/204

  of organic photoresist masks · CPC title

• H10P76/20

  of masks comprising organic materials · CPC title

• C08F222/103

  of trialcohols, e.g. trimethylolpropane tri(meth)acrylate · CPC title

• C08F222/102

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

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title