Fluorine-containing polymerisable monomer and polymer prepared by using same
View Patent ↗The present invention relates to a polymerizable monomer represented by the general formula (1), wherein R 1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a fluorine-containing alkyl group; R 2 is a straight-chain or branched alkyl group, a cyclic alkyl group, an aromatic group, or a substituent having at least two of these groups, the R 2 being optionally partially fluorinated; R 3 is a hydrogen atom, a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, the R 3 optionally containing a bond of an oxygen atom or carbonyl group; and n is an integer of 1-2.
1. A polymer prepared by polymerizing a polymerizable monomer represented by the formula (1),
wherein
R 1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a fluorine-containing alkyl group;
R 2 is an alkyl group that has a carbon atom number of at least three and that is optionally branched;
R 3 is a hydrogen atom, a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, said R 3 optionally containing an oxygen atom or carbonyl group; and
n is an integer of 1-2.
2. A polymer according to claim 1 , wherein R 1 is a hydrogen atom, methyl group, trifluoromethyl group, or nonafluoro-n-butyl group.
3. A polymer according to claim 1 , wherein R 1 is a methyl group.
4. A polymer according to claim 1 , wherein R 3 is a hydrogen atom.
5. A polymer according to claim 1 , wherein R 1 is a methyl group, and R 3 is a hydrogen atom.
6. A polymer according to claim 1 , which is prepared by polymerizing the polymerizable monomer with another comonomer.
7. A polymer according to claim 6 , wherein the another comonomer is at least one selected from the group consisting of olefins, fluorine-containing olefins, acrylic esters, methacrylic esters, fluorine-containing acrylic esters, fluorine-containing methacrylic esters, norbornene compounds, fluorine-containing norbornene compounds, styrene compounds, fluorine-containing styrene compounds, vinyl ethers, and fluorine-containing vinyl ethers.
8. A polymer according to claim 1 , which has a number average molecular weight of from 1,000 to 100,000.
9. A polymer prepared by polymerizing a polymerizable monomer represented by the formula (1),
wherein
R 1 is a halogen atom;
R 2 is an alkyl group that has a carbon atom number of at least three and that is optionally branched;
R 3 is a hydrogen atom, a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, said R 3 optionally containing an oxygen atom or carbonyl group; and
n is an integer of 1-2.
10. A polymer according to claim 9 , wherein R 3 is a hydrogen atom.
11. A polymer according to claim 9 , which is prepared by polymerizing the polymerizable monomer with another comonomer.
12. A polymer according to claim 11 , wherein the another comonomer is at least one selected from the group consisting of olefins, fluorine-containing olefins, acrylic esters, methacrylic esters, fluorine-containing acrylic esters, fluorine-containing methacrylic esters, norbornene compounds, fluorine-containing norbornene compounds, styrene compounds, fluorine-containing styrene compounds, vinyl ethers, and fluorine-containing vinyl ethers.
13. A polymer according to claim 9 , which has a number average molecular weight of from 1,000 to 100,000.
14. A polymer prepared by polymerizing a polymerizable monomer represented by the formula (1),
wherein
R 1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a fluorine-containing alkyl group;
R 2 is an alkyl group that has a carbon atom number of at least three and that is optionally branched;
R 3 is a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, said R 3 optionally containing an oxygen atom or carbonyl group; and
n is an integer of 1-2.
15. A polymer according to claim 14 , wherein R 1 is a hydrogen atom, methyl group, trifluoromethyl group, or nonafluoro-n-butyl group.
16. A polymer according to claim 14 , wherein R 1 is a methyl group.
17. A polymer according to claim 14 , which is prepared by polymerizing the polymerizable monomer with another comonomer.
18. A polymer according to claim 17 , wherein the another comonomer is at least one selected from the group consisting of olefins, fluorine-containing olefins, acrylic esters, methacrylic esters, fluorine-containing acrylic esters, fluorine-containing methacrylic esters, norbornene compounds, fluorine-containing norbornene compounds, styrene compounds, fluorine-containing styrene compounds, vinyl ethers, and fluorine-containing vinyl ethers.
19. A polymer according to claim 14 , which has a number average molecular weight of from 1,000 to 100,000.
20. A reflection preventive material, optical device material or resist material comprising a polymer prepared by polymerizing a polymerizable monomer represented by the formula (1),
wherein
R 1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a fluorine-containing alkyl group;
R 2 is an alkyl group that has a carbon atom number of at least three and that is optionally branched;
R 3 is a hydrogen atom, a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, said R 3 optionally containing an oxygen atom or carbonyl group; and
n is an integer of 1-2.
21. A material according to claim 20 , wherein R 1 is a hydrogen atom, methyl group, trifluoromethyl group, or nonafluoro-n-butyl group.
22. A material according to claim 20 , wherein R 1 is a methyl group.
23. A material according to claim 20 , wherein R 3 is a hydrogen atom.
24. A material according to claim 20 , wherein R 1 is a methyl group, and R 3 is a hydrogen atom.
25. A material according to claim 20 , wherein the polymer is prepared by polymerizing the polymerizable monomer with another comonomer.
26. A material according to claim 25 , wherein the another comonomer is at least one selected from the group consisting of olefins, fluorine-containing olefins, acrylic esters, methacrylic esters, fluorine-containing acrylic esters, fluorine-containing methacrylic esters, norbornene compounds, fluorine-containing norbornene compounds, styrene compounds, fluorine-containing styrene compounds, vinyl ethers, and fluorine-containing vinyl ethers.
27. A material according to claim 20 , wherein the polymer has a number average molecular weight of from 1,000 to 100,000.
28. A reflection preventive material, optical device material or resist material comprising a polymer prepared by polymerizing a polymerizable monomer represented by the formula (1),
wherein
R 1 is a halogen atom;
R 2 is an alkyl group that has a carbon atom number of at least three and that is optionally branched;
R 3 is a hydrogen atom, a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, said R 3 optionally containing an oxygen atom or carbonyl group; and
n is an integer of 1-2.
29. A material according to claim 28 , wherein R 3 is a hydrogen atom.
30. A material according to claim 28 , wherein the polymer is prepared by polymerizing the polymerizable monomer with another comonomer.
31. A material according to claim 30 , wherein the another comonomer is at least one selected from the group consisting of olefins, fluorine-containing olefins, acrylic esters, methacrylic esters, fluorine-containing acrylic esters, fluorine-containing methacrylic esters, norbornene compounds, fluorine-containing norbornene compounds, styrene compounds, fluorine-containing styrene compounds, vinyl ethers, and fluorine-containing vinyl ethers.
32. A material according to claim 28 , wherein the polymer has a number average molecular weight of from 1,000 to 100,000.
33. A material according to claim 28 , which is a resist material.
34. A reflection preventive material, optical device material or resist material comprising a polymer prepared by polymerizing a polymerizable monomer represented by the formula (1),
wherein
R 1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a fluorine-containing alkyl group;
R 2 is an alkyl group that has a carbon atom number of at least three and that is optionally branched;
R 3 is a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, said R 3 optionally containing an oxygen atom or carbonyl group; and
n is an integer of 1-2.
35. A material according to claim 34 , wherein R 1 is a hydrogen atom, methyl group, trifluoromethyl group, or nonafluoro-n-butyl group.
36. A material according to claim 34 , wherein R 1 is a methyl group.
37. A material according to claim 34 , wherein the polymer is prepared by polymerizing the polymerizable monomer with another comonomer.
38. A material according to claim 37 , wherein the another comonomer is at least one selected from the group consisting of olefins, fluorine-containing olefins, acrylic esters, methacrylic esters, fluorine-containing acrylic esters, fluorine-containing methacrylic esters, norbornene compounds, fluorine-containing norbornene compounds, styrene compounds, fluorine-containing styrene compounds, vinyl ethers, and fluorine-containing vinyl ethers.
39. A material according to claim 34 , wherein the polymer has a number average molecular weight of from 1,000 to 100,000.
40. A material according to claim 34 , which is a resist material.