Optically active compound having polymerizable group and its polymer

1. An optically active compound having a polymerizable group represented by formula (1) or (2):

P 1 -Q 1 -(A 1 -Z 1 ) m —X 1 —(Z 1 -A 1 ) m -Q 1 -P 2   (1)

P 1 -Q 1 -(A 1 -Z 1 ) m —X 2   (2)

in formulas (1) and (2),

the ring A 1 is independently 1,4-cyclohexylene, 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl or fluorene-2,7-diyl, and in these rings, one or nonadjacent two —CH 2 — may be replaced by —O—, and in the 1,4-phenylene and fluorene-2,7-diyl, arbitrary hydrogen may be replaced by fluorine, chlorine, cyano, methyl, ethyl, methoxy, hydroxy, formyl, acetoxy, acetyl, trifluoroacetyl, difluoromethyl or trifluoromethyl;

Z 1 is independently a single bond, —O—, —COO—, —OCO—, —CH═CH—COO—, —OCO—CH═CH—, —OCO—(CH 2 ) 2 —, —(CH 2 ) 2 —COO—, —O(CH 2 ) 2 O—, —C≡C—COO—, —OCO—C≡C—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —(CH 2 ) 4 —, —(CH 2 ) 2 —, —(CF 2 ) 2 —, —CH═CH—, —CF═CF— or —C≡C—;

m is independently an integer from 1 to 5, and when m is 2 or more, each of a plurality of Z 1 may be different groups or at least two of a plurality of Z 1 may be the same group, and each of a plurality of the ring A 1 may be different rings or at least two of a plurality of the ring A 1 may be the same ring;

Q 1 is independently alkylene having 1 to 20 carbons, and in the alkylene, arbitrary hydrogen may be replaced by fluorine or chlorine and arbitrary —CH 2 — may be replaced by —O—, —COO—, —OCO—, —CH═CH— or —C≡C—;

X 1 is a divalent group having chirality represented by any one of formulas (3-1) to (3-7), and when X 1 is formula (3-5) and m is 2 to 4, Z 1 is not —COO—(CH 2 ) 2 —, —(CH 2 ) 2 —COO— or —O(CH 2 ) 2 O— and when X 1 is formula (3-5) and m is 1, Q 1 is alkylene having 1 to 20 carbons where the group next to the ring A 1 in the alkylene is not —(CH 2 ) 2 —COO—, —COO—(CH 2 ) 2 —, —O(CH 2 ) 2 O—, —O(CH 2 ) 3 — or —(CH 2 ) 3 O—;

X 2 is a monovalent group having chirality represented by any one of formulas (3-8) to (3-10);

P 1 is independently a polymerizable group represented by formula (4-1) or (4-2);

P 2 is a polymerizable group represented by any one of formulas (4-1) to (4-5):

in formulas (4-1) to (4-5), R a is independently hydrogen, halogen or alkyl having 1 to 5 carbons.

2. The optically active compound having a polymerizable group according to claim 1 , wherein in formula (1), X 1 is a divalent grouphaving chirality represented by any one of formulas (3-1) to (3-4).

3. The optically active compound having a polymerizable group according to claim 1 , wherein in formula (1), X 1 is a divalent group having chirality represented by formula (3-5) or (3-6).

4. The optically active compound having a polymerizable group according to claim 1 , wherein in formula (1), X 1 is a divalent group having chirality represented by formula (3-7).

5. The optically active compound having a polymerizable group according to claim 1 , wherein in formulas (1) and (2), the ring A 1 is independently 1,4-cyclohexylene, 1,4-phenylene or naphthalene-2,6-diyl, and in the 1,4-phenylene, arbitrary one or two hydrogens may be replaced by fluorine, methyl, methoxy or trifluoromethyl; Z 1 is independently a single bond, —COO—, —OCO—, —CH═CH—COO—, —(CH 2 ) 2 —COO—, —OCO—CH═CH—, —OCO—(CH 2 ) 2 —, —(CH 2 ) 2 — or —C≡C—; and m is independently an integer from 1 to 3.

6. The optically active compound having a polymerizable group according to claim 1 , wherein in formulas (1) and (2), Z 1 is independently a single bond, —COO— or —OCO—; Q 1 is independently alkylene having 1 to 12 carbons, and in the alkylene, arbitrary —CH 2 — may be replaced by —O—, —COO— or —OCO—; R a in formulas (4-1) to (4-5) is independently hydrogen, methyl or ethyl.

7. The optically active compound having a polymerizable group according to claim 1 , wherein in formula (1),

the ring A 1 is independently 1,4-cyclohexylene or 1,4-phenylene, and in the 1,4-phenylene, arbitrary one or two hydrogens may be replaced by fluorine or methyl;

Z 1 is independently a single bond, —COO— or —OCO—;

m is an integer from 1 to 3;

Q 1 is independently alkylene having 1 to 12 carbons, and in the alkylene, arbitrary —CH 2 — may be replaced by —O—, —COO— or —OCO—;

P 1 and P 2 are a polymerizable group represented by formula (4-1); and

R a in formula (4-1) is hydrogen.

8. The optically active compound having a polymerizable group according to claim 1 , wherein in formula (1),

the ring A 1 is independently 1,4-cyclohexylene or 1,4-phenylene, and in the 1,4-phenylene, arbitrary one or two hydrogens may be replaced by fluorine or methyl;

Z 1 is independently a single bond, —COO— or —OCO—;

m is an integer from 1 to 3;

Q 1 is independently alkylene having 1 to 12 carbons, and in the alkylene, arbitrary —CH 2 — may be replaced by —O—, —COO— or —OCO—;

P 1 and P 2 are a polymerizable group represented by formula (4-2); and

R a in formula (4-2) is hydrogen.

9. A polymerizable liquid crystal composition, comprising at least one of the optically active compound having a polymerizable group according to claim 1 and a polymerizable liquid crystal compound.

10. The polymerizable liquid crystal composition according to claim 9 , the polymerizable liquid crystal compound is at least one compound selected from compounds represented by formulas (M1) and (M2):

P 3 -Q 2 -A 2 -(Z 2 -A 2 ) n -Q 2 -P 4   (M1)

P 3 -Q 2 -A 2 -(Z 1 -A 2 ) n -R  (M2)

in formulas (M1) and (M2),

the ring A 2 is independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, fluorene-2,7-diyl or 1,3-dioxane-2,5-diyl, and in the 1,4-phenylene and fluorene-2,7-diyl, arbitrary hydrogen may be replaced by fluorine, chlorine, cyano, methyl, ethyl, methoxy, hydroxy, formyl, acetoxy, acetyl, trifluoroacetyl, difluoromethyl or trifluoromethyl;

Z 2 is independently a single bond, —O—, —COO—, —OCO—, —CH═CH—COO—, —OCO—CH═CH—, —OCO—(CH 2 ) 2 —, —(CH 2 ) 2 —COO—, —C≡C—COO—, —OCO—C≡C—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CONH—, —NHCO—, —(CH 2 ) 4 —, —(CH 2 ) 2 —, —(CF 2 ) 2 —, —CH═CH—, —CF═CF— or —C≡C—;

n is independently an integer from 1 to 5, and when n is 2 or more, each of a plurality of Z 2 may be different groups or at least two of a plurality of Z 2 may be the same group, and each of a plurality of the ring A 2 may be different rings or at least two of a plurality of the ring A 2 may be the same ring;

Q 2 is independently alkylene having 1 to 20 carbons, and in the alkylene, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH 2 — may be replaced by —O—, —COO—, —OCO—, —CH═CH— or —C≡C—;

R is fluorine, cyano, trifluoromethyl, trifluoromethoxy, alkyl having 1 to 20 carbons or alkoxy having 1 to 20 carbons; and

P 3 and P 4 are each independently a polymerizable group represented by any one of formulas (4-1) to (4-5):

in formulas (4-1) to (4-5), R a is independently hydrogen, halogen or alkyl having 1 to 5 carbons.

11. The polymerizable liquid crystal composition according to claim 10 , wherein

in formula (1) and formula (2),

the ring A 1 is independently 1,4-cyclohexylene, 1,4-phenylene or naphthalene-2,6-diyl, and in the 1,4-phenylene, arbitrary hydrogen may be replaced by fluorine, methyl, methoxy or trifluoromethyl;

Z 1 is independently a single bond, —COO—, —OCO—, —CH═CH—COO—, —(CH 2 ) 2 —COO—, —OCO—CH═CH—, —OCO—(CH 2 ) 2 —, —(CH 2 ) 2 — or —C≡C—;

m is independently an integer from 1 to 3;

Q 1 is independently alkylene having 1 to 12 carbons, and in the alkylene, arbitrary —CH 2 — may be replaced by —O—, —COO— or —OCO—; and

R a in formulas (4-1) to (4-5) is independently hydrogen, methyl or ethyl; and

in formulas (M1) and (M2),

the ring A 2 is independently 1,4-cyclohexylene or 1,4-phenylene, and in the 1,4-phenylene, arbitrary one or two hydrogens may be replaced by fluorine, methyl or trifluoromethyl;

Z 2 is independently a single bond, —O—, —COO— or —OCO—;

n is independently an integer from 1 to 3;

Q 2 is independently alkylene having 1 to 14 carbons, and in the alkylene, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH 2 — may be replaced by —O—, —COO— or —OCO—; and

R a in formulas (4-1) to (4-5) is independently hydrogen, methyl or ethyl.

12. The polymerizable liquid crystal composition according to claim 10 , wherein

in formula (1) and formula (2),

the ring A 1 is independently 1,4-cyclohexylene or 1,4-phenylene, and in the 1,4-phenylene, arbitrary one or two hydrogens may be replaced by fluorine or methyl;

Z 1 is independently a single bond, —COO— or —OCO—;

m is independently an integer from 1 to 3;

Q 1 is independently alkylene having 1 to 12 carbons, and in the alkylene, arbitrary —CH 2 — may be replaced by —O—, —COO— or —OCO—;

P 1 is independently a polymerizable group represented by formula (4-1) or (4-2);

P 2 is a polymerizable group represented by formula (4-1) when P 1 is a polymerizable group represented by formula (4-1), and P 2 is a polymerizable group represented by formula (4-2) when P 1 is a polymerizable group represented by formula (4-2); and

R a in formula (4-1) or formula (4-2) is hydrogen; and

in formula (M1),

the ring A 2 is independently 1,4-cyclohexylene or 1,4-phenylene, and in the 1,4-phenylene, one or two hydrogens may be replaced by fluorine, methyl or trifluoromethyl;

Z 2 is independently a single bond, —O—, —COO— or —OCO—;

n is 1 or 2;

Q 2 is independently alkylene having 1 to 14 carbons, and in the alkylene, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH 2 — may be replaced by —O—, —COO— or —OCO—; and

P 3 and P 4 are the same polymerizable group.

13. The polymerizable liquid crystal composition according to claim 9 , further comprising a liquid crystal compound other than the compound represented by formulas (M1) and (M2).

14. The polymerizable liquid crystal composition according to claim 9 , further comprising an optically active compound other than the compound represented by formulas (1) and (2).

15. The polymerizable liquid crystal composition according to claim 9 , further comprising a non-optically active and non-liquid crystalline polymerizable compound.

16. A polymer formed by polymerization of the polymerizable liquid crystal composition according to claim 9 .

17. The polymer according to claim 16 , wherein the polymer has the optical anisotropy.

18. The polymer according to claim 17 , wherein the polymer has optical characteristics of a negative C-plate.

19. The polymer according to claim 17 , wherein the polymer exhibits circular dichroism in the light region at a part or all of wavelengths of 350 nm to 750 nm.

20. The polymer according to claim 17 , wherein the polymer exhibits circular dichroism in the ultraviolet region at wavelengths of 100 nm to 350 nm.

21. The polymer according to claim 17 , wherein the polymer exhibits circular dichroism in the near-infrared region at wavelengths of 750 nm to 2,500 nm.

22. An optical device containing the polymerizable liquid crystal composition according to claim 9 , wherein the helical pitch is 1 nm or more and 200 nm or less.

23. An optical device containing the polymer according to claim 17 , wherein the helical pitch is 1 nm or more and 200 nm or less.

24. An article selected from the group of a polarizing plate, an optical compensator, an alignment film, a color filter, a holographic optical device, a liquid crystal display device, a cosmetic, an ornament, an anti-counterfeit detection system, a non-linear optical device and an optical storage device, each of which contains the polymerizable liquid crystal composition according to claim 9 .

25. An article selected from the group of a polarizing plate, an optical compensator, an alignment film, a color filter, a holographic optical device, a liquid crystal display device, a cosmetic, an ornament, an anti-counterfeit detection system, a non-linear optical device and an optical storage device, each of which contains the polymer according to claim 16 .