IP Library › Granted Patent US 10,472,446
Granted Patent B2
US 10,472,446 · App. 14/773,268 · Granted Nov 12, 2019

Composition, resin mold, photo imprinting method, method for manufacturing optical element, and method for manufacturing electronic element

Inventors: Risa Wada (Ichikawa, JP); Takeshi Osaki (Ichikawa, JP)
Assignee: TOYO GOSEI CO., LTD.
C08F222/10C08F290/06C08F299/024G03F7/0002G03F7/0046G03F7/027
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Quick Facts
Patent No.
US 10,472,446
App. No.
14/773,268
Granted
Nov 12, 2019
Kind
B2
Abstract

Described is a composition comprising: a compound (A) having a substituent (a) being at least either one of an acryloyl group and a methacryloyl group, and a perfluoroalkylene group; and a compound (B) having a substituent (b) being either one of an acryloyl group and a methacryloyl group, and a substituent (c) being either one of an acryloyl group and a methacryloyl group.

Claims (65)

1. A composition consisting of:

a first light curable portion consisting of

compound (A) having a substituent (a) being at least either one of an acryloyl group and a methacryloyl group, and a perfluoroalkylene group; and

compound (B) having a substituent (b) being either one of an acryloyl group and a methacryloyl group, and a substituent (c) being either one of an acryloyl group and a methacryloyl group,

wherein, compound (B) is a bifunctional or higher functional polymerizable compound,

wherein a ratio of compound (A) in the composition to compound (B) in the composition is from 40:60 to 99.9:0.1 by mass, and

wherein compound (A) is at least one selected from a compound represented by the following Formula (1) and a compound represented by the following Formula (2):

wherein, each of R 1 , R 2 , R 3 and R 4 in Formula (1) represents a substituent containing at least one of a hydrogen atom, a carbon atom, a nitrogen atom, and a sulfur atom, and

“n” in Formula (1) represents an integer of 1 to 10, and

wherein, each of R 5 , R 6 , R 7 and R 8 in Formula (2) represents a substituent containing at least one of a hydrogen atom, a carbon atom, a nitrogen atom and a sulfur atom, and

each of “m” and “r” in Formula (2) represents an integer of 1 to 30; and, optionally,

a second portion selected from the group consisting of a compound having only one acryloyl group or methacryloyl group, a polymerization initiator(s), sensitizer(s), mold release agent(s), antioxidant(s), ultraviolet absorber(s), light stabilizer(s), silane coupling agent(s), thermal polymerization inhibitor(s), leveling agent(s), surfactant(s), preservation stabilizer(s), plasticizer(s), lubricant(s), solvent(s), filler(s), antiaging agent(s), wettability-improving agent(s), and a mixture of any thereof.

2. A light curable composition consisting of:

compound (A) having a substituent (a) being at least either one of an acryloyl group and a methacryloyl group, and a perfluoroalkylene group; and

compound (B) having a substituent (b) being either one of an acryloyl group and a methacryloyl group, and a substituent (c) being either one of an acryloyl group and a methacryloyl group,

wherein, compound (B) is a bifunctional or higher functional polymerizable compound,

wherein a ratio of compound (A) in the composition to compound (B) in the composition is from 40:60 to 99.9:0.1 by mass, and

wherein compound (A) is at least one selected from a compound represented by the following Formula (1) and a compound represented by the following Formula (2):

wherein, each of R 1 , R 2 , R 3 and R 4 in Formula (1) represents a substituent containing at least one of a hydrogen atom, a carbon atom, a nitrogen atom, and a sulfur atom, and

“n” in Formula (1) represents an integer of 1 to 10, and

wherein, each of R 5 , R 6 , R 7 and R 8 in Formula (2) represents a substituent containing at least one of a hydrogen atom, a carbon atom, a nitrogen atom and a sulfur atom.

3. The composition according to claim 1 , wherein each of R 1 and R 2 in the compound represented by Formula (1) is either one of a hydrogen atom and a methyl group.

4. The composition according to claim 3 , wherein each of R 5 and R 6 in the compound represented by Formula (2) is either one of a hydrogen atom and a methyl group.

5. The composition according to claim 1 , wherein at least one of parts represented by the following Formula (3) and Formula (4) of the compound represented by Formula (1) contains any one of structures represented by the following Formula (5), Formula (6) and Formula (7),

wherein, j in Formula (5) represents 1 or 2, and

each of R 9 , R 10 , R 11 and R 12 in Formula (6) is any one of a hydrogen atom, a methyl group and a substituent represented by the following Formula (8),

wherein, in Formula (4), R 13 each independently represents a hydrogen atom or a methyl group.

6. The composition according to claim 5 ,

wherein R 11 is either one of a hydrogen atom and a methyl group, and each of R 10 and R 12 is a hydrogen atom when R 9 is the substituent represented by Formula (8),

R 12 is either one of a hydrogen atom and a methyl group, and each of R 9 and R 11 is a hydrogen atom when R 10 is the substituent represented by Formula (8),

R 9 is either one of a hydrogen atom and a methyl group, and each of R 10 and R 12 is a hydrogen atom when R 11 is the substituent represented by Formula (8), and

R 10 is either one of a hydrogen atom and a methyl group, and each of R 9 and R 11 is a hydrogen atom when R 12 is the substituent represented by Formula (8).

7. The composition according to claim 5 , wherein each of R 9 , R 10 , R 11 and R 12 is a hydrogen atom.

8. The composition according to claim 1 , wherein at least one of parts represented by the following Formula (9) and Formula (10) of the compound represented by Formula (2) contains any one of structures represented by the following Formula (11), Formula (12) and Formula (13),

wherein, k in Formula (11) represents 1 or 2, and

each of R 14 , R 15 , R 16 and R 17 in Formula (12) is any one of a hydrogen atom, a methyl group and a substituent represented by the following Formula (14),

wherein, R 18 in Formula (14) represents a hydrogen atom or a methyl group.

9. The composition according to claim 8 ,

wherein R 16 is either one of a hydrogen atom and a methyl group, and each of R 15 and R 17 is a hydrogen atom when R 14 is the substituent represented by Formula (14),

R 17 is either one of a hydrogen atom and a methyl group, and each of R 14 and R 16 is a hydrogen atom when R 15 is the substituent represented by Formula (14),

R 14 is either one of a hydrogen atom and a methyl group, and each of R 15 and R 17 is a hydrogen atom when R 16 is the substituent represented by Formula (14), and

R 15 is either one of a hydrogen atom and a methyl group, and each of R 14 and R 16 is a hydrogen atom when R 17 is the substituent represented by Formula (14).

10. The composition according to claim 8 , wherein each of R 14 , R 15 , R 16 and R 17 is a hydrogen atom.

11. The composition of claim 1 , wherein the compound (A) is represented by Formula 1:

12. The composition of claim 1 , wherein the compound (A) is represented by Formula (2):

13. The composition of claim 12 , wherein each of R 5 and R 6 in Formula 2 is independently selected from the group consisting of a hydrogen atom and a methyl group.

14. The composition according to claim 1 ,

wherein, compound (B) has a plurality of substituents with polymerization activity,

each of the plurality of substituents is either one of an acryloyl group and a methacryloyl group, and

a value being a molecular weight of compound (B) divided by a total number of the acryloyl group and the methacryloyl group contained in compound (B), is within the range of 85 to 230.

15. A method for manufacturing a resin, comprising:

curing the composition according to claim 1 .

16. A method for imprinting, comprising:

curing the composition according to claim 1 .

17. A method for manufacturing an optical element, comprising:

curing the composition according to claim 1 .

18. A method for manufacturing an electronic element, comprising:

curing the composition according to claim 1 .

19. A resin mold for imprinting, said resin mold produced by curing the composition of claim 1 into the resin mold.

20. A method of photo imprinting, the method comprising:

utilizing the resin mold of claim 19 to perform the photo imprinting.

21. A method of manufacturing a semiconductor integrated circuit, the method comprising:

utilizing the resin mold of claim 19 to manufacture the semiconductor integrated circuit.

22. A method of manufacturing a fine optical element, the method comprising:

utilizing the resin mold of claim 19 to manufacture the fine optical element.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2016
From: WADA, RISA; OSAKI, TAKESHI
To: TOYO GOSEI CO., LTD.
Reel/Frame 039000/0244 →
Priority Claims (1)
JP 2013-042352 · Mar 4, 2013 · national
Continuity (1)
Related Publication 20160017074A1 · Jan 21, 2016