Cyclohexene derivative having alkenyl, liquid crystal composition and liquid crystal display device
View Patent ↗A liquid crystal compound selected from a group of compounds represented by formula (a): wherein Ra and Rb are each independently hydrogen, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, provided that in the alkyl, —CH 2 — may be replaced by —O—, but plural —O— are not adjacent to each other, and hydrogen may be replaced by fluorine; ring A 1 and ring A 2 are each independently trans-1,4-cyclohexylene or 1,4-phenylene, provided that one or two hydrogens of the 1,4-phenylene may be replaced by halogen, and in a 6-membered ring of these groups, one —CH 2 — or two —CH 2 — that are not adjacent to each other may be replaced by —O—, and one or two —CH═ may be replaced by —N═; Z 1 and Z 2 are each independently a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 —, —CH═CH—, —C≡—, —CH 2 O—, —OCH 2 —, —COO—, —OCO— or —OCF 2 —; l and m are each independently 0, 1 or 2, provided that l+m is 0, 1, 2 or 3; and n is an integer of from 0 to 6, provided that in —(CH 2 ) n —, —CH 2 — may be replaced by —O—, but plural —O— are not adjacent to each other, and hydrogen may be replaced by fluorine.
1. A liquid crystal compound comprising a compound selected from a group of compounds represented by formula (a):
wherein Ra and Rb are each independently hydrogen, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, provided that in the alkyl, —CH 2 — may be replaced by —O—, but plural —O— are not adjacent to each other, and hydrogen may be replaced by fluorine; ring A 1 and ring A 2 are each independently trans-1,4-cyclohexylene or 1,4-phenylene, provided that one or two hydrogens of the 1,4-phenylene may be replaced by halogen, and in a 6-membered ring of these groups, one —CH 2 — or two —CH 2 — that are not adjacent to each other may be replaced by —O—, and one or two —CH═ may be replaced by —N═; Z 1 and Z 2 are each independently a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 —, —CH═CH—, —C≡C—, —CH 2 O—, —OCH 2 —, —COO—, —OCO— or —OCF 2 —; l and m are each independently 0, 1 or 2, provided that l+m is 0, 1, 2 or 3; and n is an integer of from 0 to 6, provided that in —(CH 2 ) n —, —CH 2 — may be replaced by —O—, but plural —O— are not adjacent to each other, and hydrogen may be replaced by fluorine.
2. The liquid crystal compound according to claim 1 , wherein ring A 1 , ring A 2 and ring A 3 are each independently trans-1,4-cyclohexylene or 1,4-phenylene; Z 1 and Z 2 are each a single bond; and l+m is 0 or 1; and n is an integer of from 0 to 6.
3. The liquid crystal compound according to claim 2 , wherein Ra is hydrogen or alkyl having 1 to 10 carbons; and Rb is alkoxy having 1 to 9 carbons.
4. The liquid crystal compound according to claim 3 , wherein l+m is 1.
5. A liquid crystal composition comprising at least one compound according to claim 1 .
6. A liquid crystal composition having a negative dielectric anisotropy comprising two components, wherein the first component is at least one compound according to claim 1 , and the second component is at least one compound selected from the group of compounds represented by formulae (e-1), (e-2) and (e-3):
wherein Ra 11 and Rb 11 are each independently alkyl having 1 to 10 carbons, provided that in the alkyl, —CH 2 — that are not adjacent to each other may be replaced by —O—, —(CH 2 ) 2 — that are not adjacent to each other may be replaced by —CH═CH—, and hydrogen may be replaced by fluorine; ring A 11 , ring A 12 , ring A 13 and ring A 14 are each independently trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; and Z 11 , Z 12 and Z 13 are each independently a single bond, —CH 2 —CH 2 —, —CH═CH—, —C≡C—, —COO— or —CH 2 O—.
7. A liquid crystal composition having a negative dielectric anisotropy comprising two components, wherein the first component is at least one compound according to claim 3 , and the second component is at least one compound selected from a group of compounds represented by formulae (e-1), (e-2) and (e-3):
wherein Ra 11 and Rb 11 are each independently alkyl having 1 to 10 carbons, provided that in the alkyl, —CH 2 — that are not adjacent to each other may be replaced by —O—, —(CH 2 ) 2 — that are not adjacent to each other may be replaced by —CH═CH—, and hydrogen may be replaced by fluorine; ring A 11 , ring A 12 , ring A 13 and ring A 14 are each independently trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; and Z 11 , Z 12 and Z 13 are each independently a single bond, —CH 2 —CH 2 —, —CH═CH—, —C≡C—, —COO— or —CH 2 O—.
8. The liquid crystal composition according to claim 7 , wherein the ratio of the first component is from approximately 30% to approximately 85% by weight, and the ratio of the second component is from approximately 15% to approximately 70% by weight, based on the total weight of the liquid crystal composition.
9. The liquid crystal composition according to claim 6 , wherein the liquid crystal composition further comprises at least one compound selected from the group of compounds represented by formulae (g-1), (g-2), (g-3) and (g-4) as a third component:
wherein Ra 21 and Rb 21 are each independently hydrogen or alkyl having 1 to 10 carbons, provided that in the alkyl, —CH 2 — that are not adjacent to each other may be replaced by —O—, —(CH 2 ) 2 — that are not adjacent to each other may be replaced by —CH═CH—, and hydrogen may be replaced by fluorine; ring A 21 , ring A 22 and ring A 23 are each independently trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; Z 21 , Z 22 and Z 23 are each independently a single bond, —CH 2 C—CH 2 —, —CH═CH—, —C≡—, —OCF 2 —, —CF 2 O—, —OCF 2 CH 2 CH 2 —, —CH 2 CH 2 CF 2 O—, —COO—, —OCO—, —OCH 2 — or —CH 2 O—; Y 1 , Y 2 , Y 3 and Y 4 are each independently fluorine or chlorine; and q, r and s are each independently 0, 1 or 2, provided that q+r+s is 1, 2 or 3, and t is 0, 1 or 2.
10. The liquid crystal composition according to claim 9 , wherein the third component is at least one compound selected from a group of compounds represented by formulae (h-1), (h-2), (h-3), (h-4) and (h-5):
wherein Ra 22 is linear alkyl having 1 to 8 carbons or linear alkenyl having 2 to 8 carbons; Rb 22 is linear alkyl having 1 to 8 carbons, linear alkenyl having 2 to 8 carbons or alkoxy having 1 to 7 carbons; Z 24 is a single bond or —CH 2 CH 2 —; and both Y 1 and Y 2 are fluorine, or one of Y 1 and Y 2 is fluorine, and the other is chlorine.
11. A liquid crystal composition having a negative dielectric anisotropy comprising three components, wherein the first component is at least one compound according to claim 3 , the second component is at least one compound selected from the group of compounds represented by formulae (e-1), (e-2) and (e-3):
wherein Ra 11 and Rb 11 are each independently alkyl having 1 to 10 carbons, provided that in the alkyl, —CH 2 — that are not adjacent to each other may be replaced by —O—, —(CH 2 ) 2 — that are not adjacent to each other may be replaced by —CH═CH—, and hydrogen may be replaced by fluorine; ring A 11 , ring A 12 , ring A 13 and ring A 14 are each independently trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; and Z 11 , Z 12 and Z 13 are each independently a single bond, —CH 2 —CH 2 —, —CH═CH—, —C≡C—, —COO— or —CH 2 O—; and the third component is at least one compound selected from the group of compounds represented by formulae (h-1), (h-2), (h-3), (h-4) and (h-5):
wherein Ra 22 is linear alkyl having 1 to 8 carbons or linear alkenyl having 2 to 8 carbons; Rb 22 is linear alkyl having 1 to 8 carbons, linear alkenyl having 2 to 8 carbons or alkoxy having 1 to 7 carbons; Z 24 is a single bond or —CH 2 CH 2 —; and both Y 1 and Y 2 are fluorine, or one of Y 1 and Y 2 is fluorine, and the other is chlorine.
12. The liquid crystal composition according to claim 11 , wherein the ratio of the first component is from approximately 10 to approximately 80% by weight, the ratio of the second component is from approximately 10% to approximately 80% by weight, and the ratio of the third component is from approximately 10% to approximately 80% by weight, based on the total weight of the liquid crystal composition.
13. The liquid crystal composition according to claim 11 , wherein the liquid crystal composition further comprises at least one of an antioxidant and an ultraviolet light absorbent.
14. The liquid crystal composition according to claim 13 , wherein the antioxidant is at least one antioxidant represented by formula (I):
wherein w is an integer of 1 to 15.
15. A liquid display device comprising the liquid crystal composition according to claim 5 .
16. A liquid display device comprising the liquid crystal composition according to claim 7 .
17. The liquid crystal display device according to claim 15 , wherein the liquid crystal display device has an operation mode of a VA mode or an IPS mode, and has a driving mode of an active matrix mode.
18. The liquid crystal display device according to claim 16 , wherein the liquid crystal display device has an operation mode of a VA mode or an IPS mode, and has a driving mode of an active matrix mode.