Polymerizable compound and composition, liquid crystal composite, optical anisotropic body, liquid crystal display device and use thereof

1. A polymerizable composition, containing at least one polymerizable compound represented by formula (1):

wherein, in formula (1),

P 1 and P 2 are independently a polymerizable group, wherein the polymerizable group comprises maleimide as a monovalent group represented by formula (A), acryloyloxy (P-1), vinyloxy (P-2) or oxiranyl (P-3);

in (P-1), M 1 and M 2 are independently hydrogen, fluorine, methyl or trifluoromethyl,

in formula (A), R 1 and R 2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the alkyl having 1 to 20 carbons in which at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, at least one hydrogen may be replaced by halogen;

in formula (1), S 1 and S 2 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C— and in the divalent groups, at least one hydrogen may be replaced by halogen or alkyl having 1 to 3 carbons;

R 4 and R 5 are independently hydrogen, halogen, —S 1 —P 1 , —S 2 —P 2 or alkyl having 1 to 20 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the alkyl in which at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, at least one hydrogen may be replaced by halogen;

a1 and a2 are independently 0, 1, 2, 3 or 4;

a total number of —S 1 —P 1 and —S 2 —P 2 is 1 to 8, and at least one of —S 1 —P 1 and —S 2 —P 2 is the monovalent group represented by formula (A);

and

in formula (1),

ring A 1 and ring A 2 are independently a divalent group derived from alicyclic hydrocarbon having 3 to 18 carbons, aromatic hydrocarbon having 6 to 18 carbons or heteroaromatic hydrocarbon having 3 to 18 carbons, and in the divalent groups, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 1 to 12 carbons or alkenyloxy having 2 to 12 carbons, and in the monovalent hydrocarbon groups, at least one hydrogen may be replaced by halogen;

Z 1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one —CH 2 —CH 2 — may be replaced by —CH═CH—, —C(CH 3 )═CH—, —CH═C(CH 3 )—, —C(CH 3 )═C(CH 3 )— or —CH≡CH—, and in divalent groups, at least one hydrogen may be replaced by halogen; and

b1 is 0, 1, 2 or 3;

wherein,

when a1=0, R 4 is hydrogen, —S 1 —P 1 or alkyl having 2 to 20 carbons, with a proviso that R 4 is not the monovalent group represented by formula (A), wherein in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—,

when a2=0, R 5 is not the monovalent group represented by formula (A),

when b1=0 and a1 is 1 or 2, then R 5 is —S 2 —P 2 and R 4 is not hydrogen, or R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 1 or P 2 is not hydrogen,

when b1=1, a1=0, a2=1, and R 4 is —S 1 —P 1 , then at least one of ring A 1 and ring A 2 is not an aromatic hydrocarbon having 6 to 18 carbons, or R 5 is not hydrogen, or R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 1 is different from R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 2 ;

when b1=1, a1=1, a2=0, and R 5 is —S 2 —P 2 , then at least one of ring A 1 and ring A 2 is not an aromatic hydrocarbon having 6 to 18 carbons, or R 4 is not hydrogen, or R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 1 is different from R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 2 ;

when b1=1, a1=1 and a2=1, then at least one of ring A 1 and ring A 2 is not an aromatic hydrocarbon having 6 to 18 carbons, or R 4 is different from R 5 , or R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 1 is different from R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 2 ,

when b1=2 or 3, a1=1, a2=0 and R 5 is —S 2 —P 2 , then at least one of ring A 1 and ring A 2 is not an aromatic hydrocarbon having 6 to 18 carbons, or R 4 is not hydrogen or —S 1 —P 1 or R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 1 is different from R 1 or R 2 of the monovalent group represented by formula (A) in the polymerizable group P 2 , or Z 1 s are different from each other; and

when b1=2 or 3 and a1=0, then a2≥1.

2. The polymerizable composition according to claim 1 , wherein the at least one polymerizable compound is represented by any one of formula (1-1-1) to formula (1-1-3):

wherein, in formula (1-1-1) to formula (1-1-3),

R 1 and R 2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the alkyl in which at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, at least one hydrogen may be replaced by halogen;

R 4 is hydrogen, —S 1 —P 1 or alkyl having 2 to 20 carbons, with a proviso that R 4 is not the monovalent group represented by formula (A), wherein in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—;

S 1 and S 2 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one hydrogen may be replaced by halogen or alkyl having 1 to 3 carbons;

P 1 is a polymerizable group;

ring A 1 , ring A 2 and ring A 3 are independently a divalent group derived from alicyclic hydrocarbon having 3 to 18 carbons, aromatic hydrocarbon having 6 to 18 carbons or heteroaromatic hydrocarbon having 3 to 18 carbons, and in the divalent groups, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 1 to 12 carbons or alkenyloxy having 2 to 12 carbons, and in the monovalent hydrocarbon groups, at least one hydrogen may be replaced by halogen; and

Z 1 and Z 2 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one —CH 2 —CH 2 — may be replaced by —CH═CH—, —C(CH 3 )═CH—, —CH═C(CH 3 )—, —C(CH 3 )═C(CH 3 )— or —CH═CH—, and in the divalent groups, at least one hydrogen may be replaced by halogen.

3. The polymerizable composition according to claim 1 , wherein the at least one polymerizable compound is represented by any one of formula (1-1-4) to formula (1-1-6):

wherein, in formula (1-1-4) to formula (1-1-6),

R 1 and R 2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the alkyl in which at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, at least one hydrogen may be replaced by halogen;

R 4 is hydrogen, —S 1 —P 1 or alkyl having 2 to 20 carbons, with a proviso that R 4 is not the monovalent group represented by formula (A), wherein in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—;

S 1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one hydrogen may be replaced by halogen or alkyl having 1 to 3 carbons;

P 1 is a polymerizable group; and

ring A 1 , ring A 2 and ring A 3 are independently a divalent group derived from alicyclic hydrocarbon having 3 to 18 carbons, aromatic hydrocarbon having 6 to 18 carbons or heteroaromatic hydrocarbon having 3 to 18 carbons, and in the divalent groups, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 1 to 12 carbons or alkenyloxy having 2 to 12 carbons, and in the monovalent hydrocarbon groups, at least one hydrogen may be replaced by halogen.

4. The polymerizable composition according to claim 1 , wherein the at least one polymerizable compound is represented by formula (1-1-5):

wherein, in formula (1-1-5),

R 1 and R 2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the alkyl in which at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, at least one hydrogen may be replaced by halogen;

R 4 is hydrogen, —S 1 —P 1 or alkyl having 2 to 20 carbons, with a proviso that R 4 is not the monovalent group represented by formula (A), wherein in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—; and

ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene and 1,4-phenylene, and at least one hydrogen on the rings may be replaced by halogen.

5. The polymerizable composition according to claim 1 , wherein the at least one polymerizable compound is represented by formula (1-1-7):

wherein, in formula (1-1-7),

R 1 and R 2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the alkyl in which at least one —CH 2 — may be replaced by —O— or —S—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH—, at least one hydrogen may be replaced by halogen;

ring A 1 and ring A 2 are independently 1,4-cyclohexylene and 1,4-phenylene, and at least one hydrogen on the rings may be replaced by halogen; and

Z 1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one —CH 2 —CH 2 — may be replaced by —CH═CH—, —C(CH 3 )═CH—, —CH═C(CH 3 )—, —C(CH 3 )═C(CH 3 )— or —CH≡CH—, and in the divalent groups, at least one hydrogen may be replaced by halogen.

6. The polymerizable composition according to claim 1 , further containing at least one compound selected from the group of compounds represented by formulas (2) to (4):

wherein, in formulas (2) to (4),

R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl or the alkenyl, at least one —CH 2 — may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;

ring B 1 , ring B 2 , ring B 3 and ring B 4 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or pyrimidine-2,5-diyl; and

Z 11 , Z 12 and Z 13 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C— or —COO—.

7. The polymerizable composition according to claim 1 , further containing at least one compound selected from the group of compounds represented by formulas (5) to (7):

wherein, in formulas (5) to (7),

R 13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one —CH 2 — may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;

X 11 is fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 or —OCF 2 CHFCF 3 ;

ring C 1 , ring C 2 and ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z 14 and Z 16 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —CF 2 O—, —OCF 2 —, —CH 2 O— or —(CH 2 ) 4 —; and

L 11 and L 12 are independently hydrogen or fluorine.

8. The polymerizable composition according to claim 1 , further containing at least one compound selected from the group of compounds represented by formula (8):

wherein, in formula (8),

R 14 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one —CH 2 — may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;

X 12 is —C≡N or —C≡C—C≡N;

ring D 1 is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z 17 is a single bond, —CH 2 CH 2 —, —C≡C—, —COO—, —CF 2 O—, —OCF 2 —, or —CH 2 O—;

L 13 and L 14 are independently hydrogen or fluorine; and

i is 1, 2, 3 or 4.

9. A liquid crystal composite, formed by polymerization of the polymerizable composition according to claim 1 .

10. An optical anisotropic body, formed by polymerization of the polymerizable composition according to claim 1 .

11. A liquid crystal display device, including the polymerizable composition according to claim 1 .

12. A method of using the polymerizable compound according to claim 1 , comprising:

polymerizing the polymerizable composition containing the polymerizable compound and a liquid crystal composition to form a liquid crystal device.

13. A liquid crystal display device, including the liquid crystal composite according to claim 9 .