Polymerizable composition, antireflection film, polarizing plate and image display device each using the same, and water-repellent or oil-repellent film

1. A polymerizable composition comprising:

a compound (A) having a repeating unit having a perfluoropolyether structure and 4 or more polymerizable groups and represented by the following general formula (I) or (II):

wherein

in the general formulae (I) and (II),

each of Rf and Rf′ independently represents a perfluoroalkylene group represented by any one of the following general formulae (III-1) to (III-6);

n1 represents a repeating number of the repeating unit and represents an integer of from 5 to 50, and each of the repeating units of the n1 number may be the same as or different from every other repeating unit;

n2 represents a repeating number of the repeating unit and represents an integer of from 5 to 50, and each of the repeating units of the n2 number may be the same as or different from every other repeating unit;

each of Rf 1 , Rf′ 1 , Rf 2 , and Rf′ 2 independently represents a perfluoroalkylene group having from 1 to 10 carbon atoms or a perfluoroalkylene group having at least one ether bond and having from 2 to 10 carbon atoms;

L 1 represents an aliphatic (p1+1)-valent connecting group, and L 2 represents an aliphatic (p3+1)-valent connecting group;

L 3 represents an aliphatic (p6+1)-valent connecting group, and L 4 represents an aliphatic (p8+1)-valent connecting group;

each of p2 and p4 independently represents an integer of 1 or more;

each of p5 and p7 independently represents an integer of 1 or more;

each of p1 and p3 independently represents an integer of 2 or more;

each of p6 and p8 independently represents an integer of 2 or more;

each of Y 1 and Y 2 independently represents a divalent or multivalent connecting group having at least one group selected from the group consisting of an aliphatic group having 4 or more carbon atoms and an aromatic group, each group optionally having an ether bond;

each of Y 3 and Y 4 independently represents a divalent or multivalent connecting group having at least one group selected from the group consisting of an aliphatic group having 4 or more carbon atoms and an aromatic group, each group optionally having an ether bond but not having an amide bond;

each of X 1 and X 2 independently represents a group having a polymerizable group; and

each of X 3 and X 4 independently represents a group having a polymerizable group,

in the general formulae (III-1) to (III-6),

each of Rf 3 to Rf 6 , Re to Rf 12 , Rf 13 to Rf 20 , Rf 21 to Rf 30 , Rf 31 to Rf 42 , and Rf 43 to Rf 56 independently represents a fluorine atom, a linear perfluoroalkyl group having from 1 to 10 carbon atoms, or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 11 carbon atoms,

wherein in the general formula (III-1), at least one of Rf 3 to Rf 6 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; in the general formula (III-2), at least one of Re to Rf 12 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; in the general formula (III-3), at least one of Rf 13 to Rf 20 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; in the general formula (III-4), at least one of Rf 21 to Rf 30 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; in the general formula (III-5), at least one of Rf 31 to Rf 42 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; and in the general formula (III-6), at least one of Rf 43 to Rf 56 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms.

2. The polymerizable composition according to claim 1 ,

wherein among the repeating units in the general formula (III-1), the kind of the groups represented by Rf 3 to Rf 6 and the number of the groups are identical with each other; among the repeating units in the general formula (III-2), the kind of the groups represented by Re to Rf 12 and the number of the groups are identical with each other; among the repeating units in the general formula (III-3), the kind of the groups represented by Rf 13 to Rf 20 and the number of the groups are identical with each other; among the repeating units in the general formula (III-4), the kind of the groups represented by Rf 21 to Rf 30 and the number of the groups are identical with each other; among the repeating units in the general formula (III-5), the kind of the groups represented by Rf 31 to Rf 42 and the number of the groups are identical with each other; and among the repeating units in the general formula (III-6), the kind of the groups represented by Rf 43 to Rf 56 and the number of the groups are identical with each other.

3. The polymerizable composition according to claim 1 ,

wherein each of Rf 1 , Rf′ 1 , Rf 2 , and Rf′ 2 is independently a group represented by any one of the following formulae:

wherein n3 represents an integer of from 1 to 10.

4. The polymerizable composition according to claim 1 ,

wherein each of L 1 , L 2 , L 3 , and L 4 is independently a connecting group represented by any one of the following formulae:

wherein R represents an alkyl group;

* represents a site connecting to the adjacent oxygen atom in the general formula (I) or a site connecting to Y 3 or Y 4 in the general formula (II); and

** represents a site connecting to Y 1 or Y 2 in the general formula (I) or a site connecting to X 3 or X 4 in the general formula (II).

5. The polymerizable composition according to claim 1 ,

wherein each of Y 1 and Y 2 , and Y 3 and Y 4 is independently a connecting group represented by any one of the following formulae:

wherein each of n4, n5, and n6 independently represents an integer of from 2 to 10;

*1 represents a site connecting to L 1 or L 2 in the general formula (I) or a site connecting to the adjacent oxygen atom in the general formula (II); and

*2 represents a site connecting to X 1 or X 2 in the general formula (I) or a site connecting to L 3 or L 4 in the general formula (II).

6. The polymerizable composition according to claim 1 ,

wherein the group having a polymerizable group regarding X 1 , X 2 , X 3 , or X 4 is a (meth)acryloyl group.

7. The polymerizable composition according to claim 1 , further comprising:

(B) a photopolymerization initiator and

(C) an organic solvent.

8. An antireflection film comprising a transparent support having thereon at least one low refractive index layer,

wherein the low refractive index layer is formed of the polymerizable composition according to claim 1 .

9. A polarizing plate comprising a polarization film and two protective films protecting the both surfaces of the polarization film,

wherein at least one of the protective films is the antireflection film according to claim 8 .

10. An image display device comprising:

a display, and

the antireflection film according to claim 8 on the outermost surface of the display.

11. A water-repellent or oil-repellent film formed of the polymerizable composition according to claim 1 .

12. A method for producing an antireflection film having at least one low refractive index layer on a transparent support, which comprises:

a step of coating and drying the polymerizable composition according to claim 1 , to form the low refractive index layer.

13. A method for producing the antireflection film of claim 12 , comprising:

producing a water-repellent or oil-repellent film formed of the polymerizable composition according to claim 1 .

14. A compound (A) having a repeating unit having a perfluoropolyether structure and 4 or more polymerizable groups and represented by the following general formula (I) or (II):

wherein

in the general formulae (I) and (II),

each of Rf and Rf′ independently represents a perfluoroalkylene group represented by any one of the following general formulae (III-1) to (III-6);

n1 represents a repeating number of the repeating unit and represents an integer of from 5 to 50, and each of the repeating units of the n1 number may be the same as or different from every other repeating unit;

n2 represents a repeating number of the repeating unit and represents an integer of from 5 to 50, and each of the repeating units of the n2 number may be the same as or different from every other repeating unit;

each of Rf 1 , Rf′ 1 , Rf 2 , and Rf′ 2 independently represents a perfluoroalkylene group having from 1 to 10 carbon atoms or a perfluoroalkylene group having at least one ether bond and having from 2 to 10 carbon atoms;

L 1 represents an aliphatic (p1+1)-valent connecting group, and L 2 represents an aliphatic (p3+1)-valent connecting group;

L 3 represents an aliphatic (p6+1)-valent connecting group, and L 4 represents an aliphatic (p8+1)-valent connecting group;

each of p2 and p4 independently represents an integer of 1 or more;

each of p5 and p7 independently represents an integer of 1 or more;

each of p1 and p3 independently represents an integer of 2 or more;

each of p6 and p8 independently represents an integer of 2 or more;

each of Y 1 and Y 2 independently represents a divalent or multivalent connecting group having at least one group selected from the group consisting of an aliphatic group having 4 or more carbon atoms and an aromatic group, each group optionally having an ether bond;

each of Y 3 and Y 4 independently represents a divalent or multivalent connecting group having at least one group selected from the group consisting of an aliphatic group having 4 or more carbon atoms and an aromatic group, each group optionally having an ether bond but not having an amide bond;

each of X 1 and X 2 independently represents a group having a polymerizable group; and

each of X 3 and X 4 independently represents a group having a polymerizable group,

in the general formulae (III-1) to (III-6),

each of Rf 3 to Rf 6 , R f7 to Rf 12 , Rf 13 to Rf 20 , Rf 21 to Rf 30 , Rf 31 to Rf 42 , and Rf 43 to Rf 56 independently represents a fluorine atom, a linear perfluoroalkyl group having from 1 to 10 carbon atoms, or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 11 carbon atoms,

wherein in the general formula (III-1), at least one of Rf 3 to Rf 6 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; in the general formula (III-2), at least one of Rf 7 to Rf 12 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; in the general formula (III-3), at least one of Rf 13 to Rf 20 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; in the general formula (III-4), at least one of Rf 21 to Rf 30 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; in the general formula (III-5), at least one of Rf 31 to Rf 42 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms; and in the general formula (III-6), at least one of Rf 43 to Rf 56 is a linear perfluoroalkyl group having from 1 to 8 carbon atoms or a linear perfluoroalkyl group having at least one ether bond and having from 2 to 9 carbon atoms.