Fluorovinyl derivative, liquid crystal composition and liquid crystal display device
View Patent ↗To provide a liquid crystal compound having general physical properties required for the compound, namely, a high stability to heat, light and so forth, a small viscosity, a refractive index anisotropy value having a suitable magnitude, a dielectric constant anisotropy value having a suitable magnitude and steep electro-optical characteristics, a wide temperature range of a nematic phase, and an excellent compatibility with other liquid crystal compounds, in particular, a liquid crystal compound having a wide temperature range of the nematic phase; the compound is represented by formula (1): wherein R is alkenyl having 2 to 20 carbons; ring A 1 and ring A 2 are independently 1,4-cyclohexylene, or 1,4-phenylene in which at least one of hydrogen may be replaced by fluorine; Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —CH 2 O— or —OCH 2 —; and n is 0 or 1.
1. A compound represented by formula (1):
wherein R is alkenyl having 2 to 20 carbons; ring A 1 is 1,4-cyclohexylene or 1,4-phenylene in which at least one of hydrogen may be replaced by fluorine; and Z 1 is a single bond, —CH 2 CH 2 —, —CH═CH—, —CH 2 O— or —OCH 2 .
2. The compound according to claim 1 , wherein, in formula (1), R is alkenyl having 2 to 20 carbons; and ring A 1 is 1,4-cyclohexylene, Z 1 is a single bond and n is 0.
3. A liquid crystal composition containing at least one compound according to claim 1 .
4. The liquid crystal composition according to claim 3 , further containing at least one compound selected from the group of compounds represented by formulas (2), (3) and (4):
wherein R 3 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of hydrogen may be replaced by fluorine and at least one of —CH 2 — may be replaced by —O—;
X 1 is fluorine, chlorine, —OCF 3 —, —OCHF 2 —, —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 or —OCF 2 CHFCF 3 ;
ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 1-pyran-2,5-diyl, or 1,4-phenylene in which at least one of hydrogen may be replaced by fluorine;
Z 1 and Z 2 are independently —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —CF 2 O—, —OCF 2 —, —CH═CH—, —C═C—, —CH 2 O— or a single bond; and
L 1 and L 2 are independently hydrogen or fluorine.
5. The liquid crystal composition according to claim 3 , further containing at least one compound selected from the group of compounds represented by formula (5):
wherein R 4 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of hydrogen may be replaced by fluorine and at least one of —CH 2 — may be replaced by —O—;
X 2 is —CN or —C≡C—C≡N;
ring B 1 , ring B 2 and ring B 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one of hydrogen may be replaced by fluorine, 1,3-dioxane-2,5-diyl, 1-pyran-2,5-diyl or pyrimidine-2,5-diyl;
Z 3 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 —, —C≡C—, —CH 2 O— or a single bond;
L 3 and L 4 are independently hydrogen or fluorine; and
q is 0, 1 or 2, and r is 0 or 1.
6. The liquid crystal composition according claim 3 , further containing at least one compound selected from the group of compounds represented by formulas (6), (7), (8), (9), (10) and (11):
wherein R 5 and R 6 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of hydrogen may be replaced by fluorine and at least one of —CH 2 — may be replaced by —O—;
ring C 1 , ring C 2 , ring C 3 and ring C 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one of hydrogen may be replaced by fluorine, 6-pyran-2,5-diyl or decahydro-2,6-naphthalene;
Z 4 , Z 5 , Z 6 and Z 7 independently —(CH 2 ) 2 —, —COO—, —CH 2 O—, —OCF 2 —, —OCF 2 (CH 2 ) 2 — or a single bond;
L 5 and L 6 are independently fluorine or chlorine; and
j, k, l, m, n and p are independently 0 or 1, and a sum of k, l, m and n is 1 or 2.
7. The liquid crystal composition according to claim 3 , further containing at least one compound selected from the group of compounds represented by formulas (12), (13) and (14):
wherein R 7 and R 8 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of —CH 2 — may be replaced by —O— and at least one of hydrogen may be replaced by fluorine, excluding hydrogen in —CH═CHF;
ring D 1 , ring D 2 and ring D 3 are independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; and
Z 8 and Z 9 are independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.
8. The liquid crystal composition according to claim 4 , further containing at least one compound selected from the group of compounds represented by formula (5) according to claim 5 .
9. The liquid crystal composition according to claim 4 , further containing at least one compound selected from the group of compounds represented by formulas (12), (13) and (14) according to claim 7 .
10. The liquid crystal composition according to claim 5 , further containing at least one compound selected from the group of compounds represented by formulas (12), (13) and (14) according to claim 7 .
11. The liquid crystal composition according to claim 6 , further containing at least one compound selected from the group of compounds represented by formulas (12), (13) and (14) according to claim 7 .
12. The liquid crystal composition according to claim 3 , further containing at least one optically active compound and/or at least one polymerizable compound.
13. The liquid crystal composition according to claim 3 , further containing at least one antioxidant and/or at least one ultraviolet light absorber.
14. A liquid crystal display device containing the liquid crystal composition according to claim 3 .