| CORP. SALE | Benzene-1-F-2-CF3-5-(O-CO-C6H10-Me) |
| PATENT ASSIGNEE'S COUNTRY | Japan |
| UPDATE | 04.00 |
| PATENT NUMBER | This data is not available for free |
| PATENT GRANT DATE | 18.04.00 |
| PATENT TITLE |
Fluorine-substituted liquid-crystal compound, liquid-crystal composition and liquid-crystal display device |
| PATENT ABSTRACT |
An object of the present invention is to provide a novel liquid crystalline compound having a large dielectric anisotropy, small change in threshold voltage depending on temperature, and an improved solubility to other liquid crystal materials at low temperatures, and expressed by the following general formula (1): ##STR1## wherein R represents, for example, an alkyl group or alkoxy group having 1 to 10 carbon atoms, m and n are independently 0 or 1, A.sub.1, A.sub.2, and A.sub.3 are independently, for example, trans-1,4-cyclohexylene group, 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, Z.sub.1, Z.sub.2, and Z.sub.3 independently represent --COO--, --OCO--, --(CH.sub.2).sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, or a covalent bond provided that at least one of Z.sub.1, Z.sub.2, and Z.sub.3 represents ester bond, --CH.sub.2 O--, or --OCH.sub.2 --, X represents, for example, CF.sub.3, CF.sub.2 H, and Y represents H or F. Another object of the present invention is to provide a liquid crystal composition containing the liquid crystalline compound. |
| PATENT INVENTORS | This data is not available for free |
| PATENT ASSIGNEE | This data is not available for free |
| PATENT FILE DATE | 26.09.97 |
| PATENT CT FILE DATE | 12.04.96 |
| PATENT CT NUMBER | This data is not available for free |
| PATENT CT PUB NUMBER | This data is not available for free |
| PATENT CT PUB DATE | 17.10.96 |
| PATENT FOREIGN APPLICATION PRIORITY DATA | This data is not available for free |
| PATENT REFERENCES CITED | Gray et al., "The Synthesis and Transition Temperatures of Some Fluoro-Substituted 4-Cyanophenyl and 4-Cyanobiphenyl-4'-yl 4-Pentyl- and 4-Butoxy-Benzoates", Mol. Cryst. Liq. Cryst. 1989, vol. 172, pp. 165-189. |
| PATENT PARENT CASE TEXT | This data is not available for free |
| PATENT CLAIMS |
We claim: 1. A liquid crystalline compound expressed by general formula (1) ##STR1395## wherein R represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms (any methylene group (--CH.sub.2 --) in the alkenyl group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom), m and n are independently 0 or 1, A.sub.1, A.sub.2, and A.sub.3 are independently trans-1,4-cyclohexylene group, 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, pyrimidine-2,5-diyl group, pyridine-2,5-diyl group, or 1,3-dioxane-2,5-diyl group, Z.sub.1, Z.sub.2, and Z.sub.3 independently represent --COO--, --OCO--, --(CH.sub.2).sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, or a covalent bond provided that at least one of Z.sub.1, Z.sub.2, and Z.sub.3 represents ester bond, --CH.sub.2 O--, or --OCH.sub.2 --; X represents CF.sub.3, CF.sub.2 H, CFH.sub.2, OCF.sub.3, OCF.sub.2 H, or CN, and Y represents H or F, provided that when X is CN, then n is 0, m is 1, A.sub.2 is trans-1,4-cyclohexylene group, A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which are replaced by F, Z.sub.2 represents a covalent bond, Z.sub.1 is ester bond, and Y represents F. 2. The liquid crystalline compound according to claim 1 wherein m and n are 0. 3. The liquid crystalline compound according to claim 1 wherein m is 1, and n is 0. 4. The liquid crystalline compound according to claim 1 wherein both m and n are 1. 5. The liquid crystalline compound according to claim 2 wherein A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F. 6. The liquid crystalline compound according to claim 2 wherein A.sub.1 is trans-1,4-cyclohexylene group. 7. The liquid crystalline compound according to claim 3 wherein A.sub.2 is trans-1,4-cyclohexylene group. 8. The liquid crystalline compound according to claim 4 wherein both A.sub.2 and A.sub.3 are trans-1,4-cyclohexylene group, and Z.sub.3 is a covalent bond. 9. The liquid crystalline compound according to claim 7 wherein A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, and Z.sub.2 is a covalent bond. 10. The liquid crystalline compound according to claim 7 wherein A.sub.1 is trans-1,4-cyclohexylene group, and Z.sub.2 is a covalent bond. 11. The liquid crystalline compound according to claim 7 wherein A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which are replaced by F, Z.sub.1 is ester bond, Z.sub.2 is a covalent bond, X is CN, and Y is F. 12. The liquid crystalline compound according to claim 8 wherein A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, and Z.sub.2 is a covalent bond. 13. The liquid crystalline compound according to claim 8 wherein A.sub.1 is trans-1,4-cyclohexylene group or 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, and Z.sub.1 is a covalent bond. 14. A liquid crystal composition containing at least one liquid crystalline compound defined in any one of claims 1 to 13. 15. A liquid crystal composition containing, as a first component, at least one liquid crystalline compound defined in any one of claims 1 to 13, and, as a second component, at least one compound selected from the group consisting of the compounds expressed by any one of general formulas (2), (3), and (4) ##STR1396## wherein R.sub.1 represents an alkyl group having 1 to 10 carbon atoms, X.sub.1 represents F, Cl, OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2, L.sub.1, L.sub.2, L.sub.3, and L.sub.4 independently represent H or F, Z.sub.4 and Z.sub.5 independently represent --(CH.sub.2).sub.2 --, --CH.dbd.CH--, or a covalent bond, and a is 1 or 2. 16. A liquid crystal composition containing, as a first component, at least one liquid crystalline compound defined in any one of claims 1 to 13, and, as a second component, at least one compound selected from the group consisting of the compounds expressed by any one of general formulas (5), (6), (7), (8), and (9) ##STR1397## wherein R.sub.2 represents F, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, any methylene group (--CH.sub.2 --) in the alkyl group or alkenyl group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring A represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or 1,3-dioxane-2,5-diyl group, ring B represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring C represents trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.6 represents --(CH.sub.2).sub.2 --, --COO--, or a covalent bond, L.sub.5 and L.sub.6 independently represent H or F, and b and c are independently 0 or 1, ##STR1398## wherein R.sub.3 represents an alkyl group having 1 to 10 carbon atoms, L.sub.7 represents H or F, and d is 0 or 1, ##STR1399## wherein R.sub.4 represents an alkyl group having 1 to 10 carbon atoms, rings D and E independently represent trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.7 and Z.sub.8 independently represent --COO-- or a covalent bond, Z.sub.9 represents --COO-- or --C.tbd.C--, L.sub.8 and L.sub.9 independently represent H or F, X.sub.2 represents F, OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2, provided that when X.sub.2 represents OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2, both L.sub.8 and L.sub.9 represent H; and e, f, and g are independently 0 or 1, ##STR1400## wherein R.sub.5 and R.sub.6 independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in either case any methylene group (--CH.sub.2 --) in the alkyl group or alkylene group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring G represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring H represents trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.10 represents --C.tbd.C--, --COO--, --(CH.sub.2).sub.2 --, --CH.dbd.CH--C.dbd.C--, or a covalent bond, and Z.sub.1, represents --COO-- or a covalent bond, ##STR1401## wherein R.sub.7 and R.sub.8 independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in either case any methylene group (--CH.sub.2 --) in the alkyl group or alkylene group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring I represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring J represents trans-1,4-cyclohexylene group, 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, or pyrimidine-2,5-diyl group, ring K represents trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.12 and Z.sub.14 independently represent --COO--, --(CH.sub.2).sub.2 --, or covalent bond, Z.sub.13 represents --CH.dbd.CH--, --C.tbd.C--, --COO--, or a covalent bond, and h is 0 or 1. 17. A liquid crystal display device comprising a liquid crystal composition defined in claim 1. 18. A liquid crystal composition containing, as a first component, at least one liquid crystalline compound defined in any one of claims 1 to 13, as a part of a second component, at least one liquid crystalline compound selected from the group consisting of the compounds expressed by any one of general formulas (2), (3), and (4) ##STR1402## wherein R.sub.1 represents an alkyl group having 1 to 10 carbon atoms, X.sub.1 represents F, Cl, OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2, L.sub.1, L.sub.2, L.sub.3, and L.sub.4 independently represent H or F, Z.sub.4 and Z.sub.5 independently represent --(CH.sub.2).sub.2 --, --CH.dbd.CH--, or a covalent bond, and a is 1 or 2, and as the other part of the second component, at least one liquid crystalline compound selected from the group consisting of the compounds expressed by any one of general formulas (5), (6), (7), (8), and (9) ##STR1403## wherein R.sub.2 represents F, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, any methylene group (--CH.sub.2 --) in the alkyl group or alkenyl group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring A represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or 1,3-dioxane-2,5-diyl group, ring B represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring C represents trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.6 represents --(CH.sub.2).sub.2 --, --COO--, or a covalent bond, L.sub.5 and L.sub.6 independently represent H or F, and b and c are independently 0 or 1, ##STR1404## wherein R.sub.3 represents an alkyl group having 1 to 10 carbon atoms, L.sub.7 represents H or F, and d is 0 or 1, ##STR1405## wherein R.sub.4 represents an alkyl group having 1 to 10 carbon atoms, rings D and E independently represent trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.7 and Z, independently represent --COO-- or a covalent bond, Z.sub.9 represents --COO-- or --C.tbd.C--, L.sub.8 and L.sub.9 independently represent H or F, X.sub.2 represents F, OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2, provided that when X.sub.2 represents OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2, both L.sub.8 and L9 represent H; and e, f, and g are independently 0 or 1, ##STR1406## wherein R.sub.5 and R.sub.6 independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in either case any methylene group (--CH.sub.2 --) in the alkyl group or alkylene group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring G represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring H represents trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.10 represents --C.tbd.C--, --COO--, --(CH.sub.2).sub.2 --, --CH.dbd.CH--C.tbd.C--, or a covalent bond, and Z.sub.11 represents --COO-- or a covalent bond, ##STR1407## wherein R.sub.7 and R.sub.8 independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in either case any methylene group (--CH.sub.2 --) in the alkyl group or alkylene group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring I represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring J represents trans-1,4-cyclohexylene group, 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, or pyrimidine-2,5-diyl group, ring K represents trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.12 and Z.sub.14 independently represent --COO--, --(CH.sub.2).sub.2 --, or covalent bond, Z.sub.13 represents --CH.dbd.CH--, --C.tbd.C--, --COO--, or a covalent bond, and h is 0 or 1. 19. A liquid crystal display device comprising a liquid crystal composition defined in claim 15. 20. A liquid crystal display device comprising a liquid crystal composition defined in claim 16. 21. A liquid crystal display,device comprising a liquid crystal composition defined in claim 18. -------------------------------------------------------------------------------- |
| PATENT DESCRIPTION |
TECHNICAL FIELD The present invention relates to a liquid crystalline compound and a liquid crystal composition. More specifically, the present invention relates to a novel fluorine substituted compound having 3-fluoro-4-substituted phenyl group or 3,5-difluoro-4-substituted phenyl group, a liquid crystal composition containing the fluorine substituted compound, and a liquid crystal display device comprising the liquid crystal composition. BACKGROUND ART Liquid crystal display devices comprising liquid crystalline compounds have widely been used for displays of watches, tabletop calculators, word processors, and others. These display devices employ the optical anisotropy and dielectric anisotropy of liquid crystalline compounds. While liquid crystal phase includes a nematic liquid crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase, display devices employing the nematic liquid crystal phase have most widely been used. As their display mode, dynamic scattering (DS) type, deformation of aligned phase (DAP) type, guest-host (GH) type, twisted nematic (TN) type, super twisted nematic (STN) type, and thin film transistor (TFT) type are known. Whereas liquid crystalline compounds employed in these display modes must exhibit a liquid crystal phase at a wide temperature range having its center at room temperature, must be sufficiently stable under conditions in which the liquid crystalline compounds are used, and must have characteristics sufficient to drive the display devices, no compound which satisfies those requirements by its self has been found. Accordingly, it is an actual circumstance that several kinds to several tens kinds of liquid crystalline compounds are mixed, together with not-liquid crystalline compounds when necessary, to produce a liquid crystal composition provided with required characteristics. These liquid crystal compositions are required to be stable against moisture, light, heat, and air which usually exist under the conditions in which display devices are used, to be stable against electric field and electromagnetic radiation, and further to be chemically stable against the compounds to be mixed. The liquid crystal compositions are also required to have appropriate physical parameters such as the value of optical anisotropy (.DELTA.n) and dielectric anisotropy (.DELTA..epsilon.) depending on the display mode and the shape of display devices. Still further, it is important that each of the components in the liquid crystal compositions have good solubility to each other. Especially, the demand for lowering threshold voltage still more which largely contributes to high speed response necessary for expanding the screen of liquid crystal display devices has been increased. For that purpose, liquid crystalline compounds having a large .DELTA..epsilon. are necessary (E. Jakeman et al., Phys. Lett., 39A. 69 (1972)). Also, liquid crystalline compounds having a small change of threshold voltage depending on temperature are considered to be necessary. In order to achieve these purposes, the compounds expressed by formula (a), (b), or (c) are disclosed in Laid-open Japanese Patent Publication No. Sho 55-40660, Laid-open WO Japanese Patent Publication No. Hei 2-501311, or Laid-open WO Japanese Patent Publication No. Hei 3-500413. However, .DELTA..epsilon. of these compounds is not yet sufficiently large and the change of their threshold voltage due to the change of temperature can not be said to be small. ##STR2## Further, the compounds expressed by formula (d) or (e) are known in public through Laid-open WO Japanese Patent Publication No. Hei 3-503637 or Laid-open Japanese Patent Publication No. Hei 4-279560. However, these compounds have problems that the temperature range of liquid crystal phase is narrow or the solubility to other liquid crystal materials at low temperatures is not sufficient whereas the compounds have a large .DELTA..epsilon.. ##STR3## DISCLOSURE OF THE INVENTION An object of the present invention is to solve the defects in the prior art mentioned above; particularly to provide a fluorine substituted compound which has a large .DELTA..epsilon. and small change of threshold voltage depending on temperature, is excellent in stability, and is improved in solubility to other liquid crystal materials at low temperatures; to provide a liquid crystal composition containing the compound; and to provide a liquid crystal display device comprising the liquid crystal composition. In order to achieve the objects mentioned above, the present invention is described as follows: (1) A liquid crystalline compound expressed by general formula (1) ##STR4## wherein R represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, any methylene group (--CH.sub.2 --) in the alkenyl group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, m and n are independently 0 or 1, A.sub.1, A.sub.2, and A.sub.3 are independently trans-1,4-cyclohexylene group, 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, pyrimidine-2,5-diyl group, pyridine-2,5-diyl group, or 1,3-dioxane-2,5-diyl group, Z.sub.1, Z.sub.2, and Z.sub.3 independently represent --COO--, --OCO--, --(CH.sub.2).sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, or a covalent bond is provided that at least one of Z.sub.1, Z.sub.2, and Z.sub.3 represents ester bond, --CH.sub.2 O--, or --OCH.sub.2 --; X represents CF.sub.3, CF.sub.2 H, CFH.sub.2, OCF.sub.3, OCF.sub.2 H, or CN, and Y represents H or F, provided that when X is CN, n is 0, A.sub.2 is trans-1,4-cyclohexylene group, A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, Z.sub.2 represents --(CH.sub.2).sub.2 -- or a covalent bond, Z.sub.1 is ester bond, and Y represent F. (2) The liquid crystalline compound recited in (1) above wherein m and n are 0. (3) The liquid crystalline compound recited in (1) above wherein m is 1, and n is 0. (4) The liquid crystalline compound recited in (1) wherein both m and n are 1. (5) The liquid crystalline compound recited in (2) above wherein A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F. (6) The liquid crystalline compound recited in (2) above wherein A.sub.1 is trans-1,4-cyclohexylene group. (7) The liquid crystalline compound recited in (3) above wherein A.sub.2 is trans-1,4-cyclohexylene group. (8) The liquid crystalline compound recited in (4) above wherein both A.sub.2 and A.sub.3 are trans-1,4-cyclohexylene group, and Z.sub.3 is a covalent bond. (9) The liquid crystalline compound recited in (7) above wherein A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, and Z.sub.2 is a covalent bond. (10) The liquid crystalline compound recited in (7) above wherein A.sub.1 is trans-1,4-cyclohexylene group, and Z.sub.2 is a covalent bond. (11) The liquid crystalline compound recited in (7) above wherein A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, Z.sub.1 is ester bond, Z.sub.2 is --(CH.sub.2).sub.2 -- or a covalent bond, X is CN, and Y is F. (12) The liquid crystalline compound recited in (8) above wherein A.sub.1 is 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, and Z.sub.2 is a covalent bond. (13) The liquid crystalline compound recited in (8) above wherein A.sub.1 is trans-1,4-cyclohexylene group or 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, and Z.sub.1 is a covalent bond. (14) A liquid crystal composition containing at least one liquid crystalline compound recited in any one of (1) to (13) above. (15) A liquid crystal composition containing, as a first component, at least one liquid crystalline compound recited in any one of (1) to (13) above, and containing, as a second component, at least one compound selected from the group consisting of the compounds expressed by any one of general formulas (2), (3), and (4) ##STR5## wherein R.sub.1 represents an alkyl group having 1 to 10 carbon atoms, X.sub.1 represents F, Cl, OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2, L.sub.1, L.sub.2, L.sub.3, and L.sub.4 independently represent H or F, Z.sub.4 and Z.sub.5 independently represent --(CH.sub.2).sub.2 --, --CH=CH--, or a covalent bond, and a is 1 or 2. (16) A liquid crystal composition containing, as a first component, at least one liquid crystalline compound recited in any one of (1) to (13) above, and containing, as a second component, at least one compound selected from the group consisting of the compounds expressed by any one of general formulas (5), (6), (7), (8), and (9) ##STR6## wherein R.sub.2 represents F, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, any methylene group (--CH.sub.2 --) in the alkyl group or alkenyl group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring A represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or 1,3-dioxane-2,5-diyl group, ring B represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring C represents trans-1,4-cyclohexylene group, or 1,4-phenylene group, Z.sub.6 represents --(CH.sub.2).sub.2 --, --COO--, or a covalent bond, L.sub.5 and L.sub.6 independently represent H or F, and b and c are independently 0 or 1, ##STR7## wherein R.sub.3 represents an alkyl group having 1 to 10 carbon atoms, L.sub.7 represents H or F, and d is 0 or 1, ##STR8## wherein R.sub.4 represents an alkyl group having 1 to 10 carbon atoms, rings D and E independently represent trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.7 and Z.sub.8 independently represent --COO-- or a covalent bond, Z.sub.9 represents --COO-- or --C.tbd.C--, L.sub.8 and L.sub.9 independently represent H or F, X.sub.2 represents F, OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2 provided that when X.sub.2 represents OCF.sub.3, OCF.sub.2 H, CF.sub.3, CF.sub.2 H, or CFH.sub.2, both L.sub.8 and L.sub.9 represent H; and e, f, and g are independently 0 or 1, ##STR9## wherein R.sub.5 and R.sub.6 independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in either case any methylene group (--CH.sub.2 --) in the alkyl group or alkylene group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring G represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring H represents trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.10 represents --C.tbd.C--, --COO--, --(CH.sub.2).sub.2 --, --CH.dbd.CH--C.tbd.C--, or a covalent bond, and Z.sub.11 represents --COO-- or a covalent bond, ##STR10## wherein R.sub.7 and R.sub.8 independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, in either case any methylene group (--CH.sub.2 --) in the alkyl group or alkylene group may be replaced by oxygen atom (--O--) provided that in no case two or more methylene groups are continually replaced by oxygen atom, ring 1 represents trans-1,4-cyclohexylene group, 1,4-phenylene group, or pyrimidine-2,5-diyl group, ring J represents trans-1,4-cyclohexylene group, 1,4-phenylene group one or more hydrogen atom on the ring of which may be replaced by F, or pyrimidine-2,5-diyl group, ring K represents trans-1,4-cyclohexylene group or 1,4-phenylene group, Z.sub.12 and Z.sub.14 independently represent --COO--, --(CH.sub.2).sub.2 --, or a covalent bond, Z.sub.13 represents --CH.dbd.CH--, --C.tbd.C--, --COO--, or a covalent bond, and h is 0 or 1. (17) A liquid crystal composition containing, as a first component, at least one liquid crystalline compound recited in any one of (1) to (13) above, containing, as a part of a second component, at least one liquid crystalline compound selected from the group consisting of the compounds expressed by any one of general formulas (2), (3), and (4) recited in aspect (15) above, and containing, as the other part of the second component, at least one liquid crystalline compound selected from the group consisting of the compounds expressed by any one of general formulas (5), (6), (7), (8), and (9) recited in aspect (16) above. (18) A liquid crystal display device comprising a liquid crystal composition recited in any one of (14) to (17) above. Liquid crystalline compounds of the present invention expressed by general formula (1) have a large .DELTA..epsilon. and small change of threshold voltage depending on temperature. These liquid crystalline compounds are physically and chemically stable to a sufficient extent under the conditions in which display devices are ordinarily used, and excellent in solubility at low temperatures. Further, they can be derived into compounds of desired physical parameters by suitably selecting the 6-membered ring, substituent and/or bonding group from the group of the elements which form the molecule. Accordingly, when the compound of the present invention was used as a component of liquid crystal compositions, novel liquid crystal compositions having preferable characteristics can be provided. BEST MODE FOR CARRYING OUT THE INVENTION Compounds of the present invention expressed by general formula (1) are classified as follows: In the following, Q represents the group shown just below. ##STR11## Cyc represents trans-1,4-cyclohexylene group, Phe does 1,4-phenylene group, Pyr does pyrimidine-2,5-diyl group, Pyd does pyridine-2,5-diyl group, and Dio represents 1,3-dioxane-2,5-diyl group; one or more hydrogen atoms in the Phe may be replaced by F; A.sub.1, A.sub.2, and A.sub.3 are selected from the group consisting of Cyc, Phe, Pyr, Pyd, and Dio, and preferably two or more Pyr, Pyd, or Dio are not contained in one molecule. Compounds having 2 six-membered rings: ______________________________________ R-A.sub.1 -COO-Q (1a) R-A.sub.1 -OCO-Q (1b) R-A.sub.1 -CH.sub.2 O-Q (1c) R-A.sub.1 -OCH.sub.2 -Q (1d) ______________________________________ Compounds having 3 six-membered rings: ______________________________________ R-A.sub.1 -A.sub.2 -COO-Q (1e) R-A.sub.1 -COO-A.sub.2 -Q (1f) R-A.sub.1 -A.sub.2 -OCO-Q (1g) R-A.sub.1 -OCO-A.sub.2 -Q (1h) R-A.sub.1 -(CH.sub.2).sub.2 -A.sub.2 -COO-Q (1i) R-A.sub.1 -COO-A.sub.2 -COO-Q (1j) R-A.sub.1 -A.sub.2 -CH.sub.2 O-Q (1k) R-A.sub.1 -CH.sub.2 O-A.sub.2 -Q (1l) R-A.sub.1 -A.sub.2 -OCH.sub.2 -Q (1m) R-A.sub.1 -OCH.sub.2 -A.sub.2 -Q (1n) R-A.sub.1 -(CH.sub.2).sub.2 -A.sub.2 -CH.sub.2 O-Q (1o) R-A.sub.1 -(CH.sub.2).sub.2 -A.sub.2 -OCH.sub.2 -Q (1p) ______________________________________ Compounds having 4 six-membered rings: ______________________________________ R-A.sub.1 -COO-A.sub.2 -A.sub.3 -Q (1q) R-A.sub.1 -A.sub.2 -COO-A.sub.3 -Q (1r) R-A.sub.1 -A.sub.2 -A.sub.3 -COO-Q (1s) R-A.sub.1 -COO-A.sub.2 -COO-A.sub.3 -Q (1t) R-A.sub.1 -(CH.sub.2).sub.2 -A.sub.2 -COO-A.sub.3 -Q (1u) R-A.sub.1 -A.sub.2 -(CH.sub.2).sub.2 -A.sub.3 -COO-Q (1v) R-A.sub.1 -CH.sub.2 O-A.sub.2 -A.sub.3 -Q (1w) R-A.sub.1 -A.sub.2 -CH.sub.2 O-A.sub.3 -Q (1x) R-A.sub.1 -A.sub.2 -A.sub.3 -CH.sub.2 O-Q (1y) R-A.sub.1 -A.sub.2 -OCH.sub.2 -A.sub.3 -Q (1z) ______________________________________ Compounds expressed by formula (1a) are developed further to the compounds expressed by one of the following formulas (1aa) to (1ae): ______________________________________ R-Cyc-COO-Q (1aa) R-Phe-COO-Q (1ab) R-Phr-COO-Q (1ac) R-Pyd-COO-Q (1ad) R-Dio-COO-Q (1ae) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1aa) or (1ab) are preferable. Compounds expressed by formula (1b) are developed further to the compounds expressed by one of the following formulas (1ba) to (1be): ______________________________________ R-Cyc-OCO-Q (1ba) R-Phe-OCO-Q (1bb) R-Pyr-OCO-Q (1bc) R-Pyd-OCO-Q (ibd) R-Dio-OCO-Q (1be) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1ba) or (1bb) are preferable. Compounds expressed by formula (1c) are developed further to the compounds expressed by one of the following formulas (1ca) to (1ce): ______________________________________ R-Cyc-CH.sub.2 O-Q (1ca) R-Phe-CH.sub.2 O-Q (1cb) R-Pyr-CH.sub.2 O-Q (1cc) R-Pyd-CH.sub.2 O-Q (1cd) R-Dio-CH.sub.2 O-Q (1ce) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1ca), (1cb), or (1ce) are preferable. Compounds expressed by formula (1d) are developed further to the compounds expressed by one of the following formulas (1da) to (1de): ______________________________________ R-Cyc-OCH.sub.2 -Q (1da) R-Phe-OCH.sub.2 -Q (1db) R-Pyr-OCH.sub.2 -Q (1dc) R-Pyd-OCH.sub.2 -Q (1dd) R-Dio-OCH.sub.2 -Q (1de) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1da) or (1db) are preferable. Compounds expressed by formula (1e) are developed further to the compounds expressed by any one of the following formulas (1ea) to (1ej): ______________________________________ R-Cyc-Cyc-COO-Q (1ea) R-Cyc-Phe-COO-Q (1eb) R-Phe-Cyc-COO-Q (1ec) R-Phe-Phe-COO-Q (1ed) R-Pyr-Phe-COO-Q (1ee) R-Pyr-Cyc-COO-Q (1ef) R-Pyd-Phe-COO-Q (1eg) R-Pyd-Cyc-COO-Q (1eh) R-Dio-Phe-COO-Q (1ei) R-Dio-Cyc-COO-Q (1ej) ______________________________________ Among these compounds, particularly the compounds expressed by one of the formulas (1ea) to (1ee), or formula (1ej) are preferable. Compounds expressed by formula (1f) are developed further to the compounds expressed by one of the following formulas (1fa) to (1fn): ______________________________________ R-Cyc-COO-Cyc-Q (1fa) R-Cyc-COO-Phe-Q (1fb) R-Cyc-COO-Pyr-Q (1fc) R-Cyc-COO-Pyd-Q (1fd) R-Phe-COO-Cyc-Q (1fe) R-Phe-COO-Phe-Q (1ff) R-Phe-COO-Pyr-Q (1fg) R-Phe-COO-Pyd-Q (1fh) R-Pyr-COO-Phe-Q (1fi) R-Pyr-COO-Cyc-Q (1fj) R-Pyd-COO-Phe-Q (1fk) R-Pyd-COO-Cyc-Q (1fl) R-Dio-COO-Phe-Q (1fm) R-Dio-COO-Cyc-Q (1fn) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1fa), (1fb), (1fe), or (1ff) are preferable. Compounds expressed by formula (1g) are developed further to the compounds expressed by one of the following formulas (1ga) to (1gj): ______________________________________ R-Cyc-Cyc-OCO-Q (1ga) R-Cyc-Phe-OCO-Q (1gb) R-Phe-Cyc-OCO-Q (1gc) R-Phe-Phe-OCO-Q (1gd) R-Pyr-Phe-OCO-Q (1ge) R-Pyr-Cyc-OCO-Q (1gf) R-Pyd-Phe-OCO-Q (1gg) R-Pyd-Cyc-OCO-Q (1gh) R-Dio-Phe-OCO-Q (igi) R-Dio-Cyc-OCO-Q (1gj) ______________________________________ Among these compounds, particularly the compounds expressed by one of formulas (1ga) to (1ge), or (1gi) are preferable. Compounds expressed by formula (1h) are developed further to the compounds expressed by one of the following formulas (1ha) to (1hn): ______________________________________ R-Cyc-OCO-Cyc-Q (1ha) R-Cyc-OCO-Phe-Q (1hb) R-Cyc-OCO-Pyr-Q (1hc) R-Cyc-OCO-Pyd-Q (1hd) R-Phe-OCO-Cyc-Q (1he) R-Phe-OCO-Phe-Q (ihf) R-Phe-CO-Pyr-Q (1hg) R-Phe-OCO-Pyd-Q (1hh) R-Pye-OCO-Phe-Q (1hi) R-Pyr-OCO-Cyc-Q (1hj) R-Pyd-OCO-Phe-Q (1hk) R-Pyd-OCO-Cyc-Q (1hl) R-Dio-OCO-Phe-Q (1hm) R-Dio-OCO-Cyc-Q (1hn) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1ha), (1hb), (1he), or (1hf) are preferable. Compounds expressed by formula (li) are developed further to the compounds expressed by one of the following formulas (1ia) to (1ik): ______________________________________ R-Cyc-(CH.sub.2).sub.2 -Cyc-COO-Q (1ia) R-Cyc-(CH.sub.2).sub.2 -Phe-COO-Q (1ib) R-Phe-(CH.sub.2).sub.2 -Cyc-COO-Q (1ic) R-Phe-(CH.sub.2).sub.2 -Phe-COO-Q (1id) R-Phe-(CH.sub.2).sub.2 -Pyr-COO-Q (1ie) R-Pyr-(CH.sub.2).sub.2 -Phe-COO-Q (1if) R-Pyr-(CH.sub.2).sub.2 -Cyc-COO-Q (1ig) R-Pyd-(CH.sub.2).sub.2 -Phe-COO-Q (1ih) R-Pyd-(CH.sub.2).sub.2 -Cyc-COO-Q (1ii) R-Dio-(CH.sub.2).sub.2 -Phe-COO-Q (1ij) R-Dio-(CH.sub.2).sub.2 -Cyc-COO-Q (1ik) ______________________________________ Among these compounds, particularly the compounds expressed by one of formulas (1ia) to (1id) are preferable. Compounds expressed by formula (1j) are developed further to the compounds expressed by any one of the following formulas (1ja) to (1jk): ______________________________________ R-Cyc-COO-Cyc-COO-Q (1ja) R-Cyc-COO-Phe-COO-Q (1jb) R-Phe-COO-Cyc-COO-Q (1jc) R-Phe-COO-Phe-COO-Q (1jd) R-Phe-COO-Pyr-COO-Q (1je) R-Pyr-COO-Phe-COO-Q (1jf) R-Pyr-COO-Cyc-COO-Q (1jg) R-Pyd-COO-Phe-COO-Q (1jh) R-Pyd-COO-Cyc-COO-Q (1ji) R-Dio-COO-Phe-COO-Q (1jj) R-Dio-COO-Cyc-COO-Q (1jk) ______________________________________ Among these compounds, particularly the compounds expressed by one of formulas (1ja) to (1jd) are preferable. Compounds expressed by formula (1k) are developed further to the compounds expressed by ne of the following formulas (1ka) to (1kj): ______________________________________ R-Cyc-Cyc-CH.sub.2 O-Q (1ka) R-Cyc-Phe-CH.sub.2 O-Q (1kb) R-Phe-Cyc-CH.sub.2 O-Q (1kc) R-Phe-Phe-CH.sub.2 O-Q (1kd) R-Pyr-Phe-CH.sub.2 O-Q (1ke) R.sub.9 -Pyr-Cyc-CH.sub.2 O-Q (1kf) R.sub.9 -Pyd-Phe-CH.sub.2 O-Q (1kg) R.sub.9 -Pyd-Cyc-CH.sub.2 O-Q (1kh) R.sub.9 -Dio-Phe-CH.sub.2 O-Q (1ki) R.sub.9 -Dio-Cyc-CH.sub.2 O-Q (1kj) ______________________________________ Among these compounds, particularly the compounds expressed by one of formulas (1ka) to (1ke), or formula (1ki) are preferable. Compounds expressed by formula (1l) are developed further to the compounds expressed by any one of the following formulas (1la) to (1ln): ______________________________________ R.sub.9 -Cyc-CH.sub.2 O-Cyc-Q (1la) R.sub.9 -Cyc-CH.sub.2 O-Phe-Q (1lb) R.sub.9 -Cyc-CH.sub.2 O-Pyr-Q (1lc) R.sub.9 -Cyc-CH.sub.2 O-Pyd-Q (1ld) R.sub.9 -Phe-CH.sub.2 O-Cyc-Q (1le) R.sub.9 -Phe-CH.sub.2 O-Phe-Q (1lf) R.sub.9 -Phe-CH.sub.2 O-Pyr-Q (1lg) R.sub.9 -Phe-CH.sub.2 O-Pyd-Q (1lh) R.sub.9 -Pyr-CH.sub.2 O-Phe-Q (1li) R.sub.9 -Pyr-CH.sub.2 O-Cyc-Q (1lj) R.sub.9 -Pyd-CH.sub.2 O-Phe-Q (1lk) R.sub.9 -Pyd-CH.sub.2 O-Cyc-Q (1ll) R.sub.9 -Dio-CH.sub.2 O-Phe-Q (1lm) R.sub.9 -Dio-CH.sub.2 O-Cyc-Q (1ln) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1la), (1lb), (1le), or (1lf) are referable. Compounds expressed by formula (1m) are developed further to the compounds expressed by any one of the following formulas (1ma) to (1mj): ______________________________________ R.sub.9 -Cyc-Cyc-OCH.sub.2 -Q (1ma) R.sub.9 -Cyc-Phe-OCH.sub.2 -Q (1mb) R.sub.9 -Phe-Cyc-OCH.sub.2 -Q (1mc) R.sub.9 -Phe-Phe-OCH.sub.2 -Q (1md) R.sub.9 -Pyr-Phe-OCH.sub.2 -Q (1me) R.sub.9 -Pyr-Cyc-OCH.sub.2 -Q (1mf) R.sub.9 -Pyd-Phe-OCH.sub.2 -Q (1mg) R.sub.9 -Pyd-Cyc-OCH.sub.2 -Q (1mh) R.sub.9 -Dio-Phe-OCH.sub.2 -Q (1mi) R.sub.9 -Dio-Cyc-OCH.sub.2 -Q (1mj) ______________________________________ Among these compounds, particularly the compounds expressed by any one of formulas (1ma) to (1me), or (1mi) are preferable. Compounds expressed by formula (1n) are developed further to the compounds expressed by any one of the following formulas (1na) to (1nn): ______________________________________ R.sub.9 -Cyc-OCH.sub.2 -Cyc-Q (1na) R.sub.9 -Cyc-OCH.sub.2 -Phe-Q (1nb) R.sub.9 -Cyc-OCH.sub.2 -Pyr-Q (1nc) R.sub.9 -Cyc-OCH.sub.2 -Pyd-Q (1nd) R.sub.9 -Phe-OCH.sub.2 -Cyc-Q (1ne) R.sub.9 -Phe-OCH.sub.2 -Phe-Q (1nf) R.sub.9 -Phe-OCH.sub.2 -Pyr-Q (1ng) R.sub.9 -Phe-OCH.sub.2 -Pyd-Q (1nh) R.sub.9 -Pyr-OCH.sub.2 -Phe-Q (1ni) R.sub.9 -Pyr-OCH.sub.2 -Cyc-Q (1nj) R.sub.9 -Pyd-OCH.sub.2 -Phe-Q (1nk) R.sub.9 -Pyd-OCH.sub.2 -Cyc-Q (1nl) R.sub.9 -Dio-OCH.sub.2 -Phe-Q (1nm) R.sub.9 -Dio-OCH.sub.2 -Cyc-Q (1nn) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1na), (1nb), (1ne), or (1nf) are preferable. Compounds expressed by formula (1o) are developed further to the compounds expressed by any one of the following formulas (1oa) to (1ok): ______________________________________ R.sub.9 -Cyc-(CH.sub.2).sub.2 -Cyc-CH.sub.2 O-Q (1oa) R.sub.9 -Cyc-(CH.sub.2).sub.2 -Phe-CH.sub.2 O-Q (1ob) R.sub.9 -Phe-(CH.sub.2).sub.2 -Cyc-CH.sub.2 O-Q (1oc) R.sub.9 -Phe-(CH.sub.2).sub.2 -Phe-CH.sub.2 O-Q (1od) R.sub.9 -Phe-(CH.sub.2).sub.2 -Pyr-CH.sub.2 O-Q (1oe) R.sub.9 -Pyr-(CH.sub.2).sub.2 -Phe-CH.sub.2 O-Q (1of) R.sub.9 -Pyr-(CH.sub.2).sub.2 -Cyc-CH.sub.2 O-Q (1og) R.sub.9 -Pyd-(CH.sub.2).sub.2 -Phe-CH.sub.2 O-Q (1oh) R.sub.9 -Pyd-(CH.sub.2).sub.2 -Cyc-CH.sub.2 O-Q (1oi) R.sub.9 -Dio-(CH.sub.2).sub.2 -Phe-CH.sub.2 O-Q (1oj) R.sub.9 -Dio-(CH.sub.2).sub.2 -Cyc-CH.sub.2 O-Q (1ok) ______________________________________ Among these compounds, the compounds expressed by any one of formulas (1oa) to (1od) are preferable. Compounds expressed by formula (1p) are developed further to the compounds expressed by any one of the following formulas (1pa) to (1pk): ______________________________________ R.sub.9 -Cyc-(CH.sub.2).sub.2 -Cyc-OCH.sub.2 -Q (1pa) R.sub.9 -Cyc-(CH.sub.2).sub.2 -Phe-OCH.sub.2 -Q (1pb) R.sub.9 -Phe-(CH.sub.2).sub.2 -Cyc-OCH.sub.2 -Q (1pc) R.sub.9 -Phe-(CH.sub.2).sub.2 -Phe-OCH.sub.2 -Q (1pd) R.sub.9 -Phe-(CH.sub.2).sub.2 -Pyr-OCH.sub.2 -Q (1pe) R.sub.9 -Pyr-(CH.sub.2).sub.2 -Phe-OCH.sub.2 -Q (1pf) R.sub.9 -Pyr-(CH.sub.2).sub.2 -Cyc-OCH.sub.2 -Q (1pg) R.sub.9 -Pyd-(CH.sub.2).sub.2 -Phe-OCH.sub.2 -Q (1ph) R.sub.9 -Pyd-(CH.sub.2).sub.2 -Cyc-OCH.sub.2 -Q (1pi) R.sub.9 -Dio-(CH.sub.2).sub.2 -Phe-OCH.sub.2 -Q (1pj) R.sub.9 -Dio-(CH.sub.2).sub.2 -Cyc-OCH.sub.2 -Q (1pk) ______________________________________ Among these compounds, particularly the compounds expressed by any one of formulas (1pa) to (1pd) are preferable. Compounds expressed by formula (1q) are developed further to the compounds expressed by one of the following formulas (1qa) to (1qh): ______________________________________ R.sub.9 -Cyc-COO-Cyc-Cyc-Q (1qa) R.sub.9 -Cyc-COO-Cyc-Phe-Q (1qb) R.sub.9 -Cyc-COO-Phe-Phe-Q (1qc) R.sub.9 -Cyc-COO-Phe-Cyc-Q (1qd) R.sub.9 -Phe-COO-Cyc-Cyc-Q (1qe) R.sub.9 -Phe-COO-Cyc-Phe-Q (1qf) R.sub.9 -Phe-COO-Phe-Cyc-Q (1qg) R.sub.9 -Phe-COO-Phe-Phe-Q (1qh) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1qb), (1qc), (1qf), or (1qh) are preferable. Compounds expressed by formula (1r) are developed further to the compounds expressed by one of the following formulas (1ra) to (1rh): ______________________________________ R.sub.9 -Cyc-Cyc-COO-Cyc-Q (1ra) R.sub.9 -Cyc-Cyc-COO-Phe-Q (1rb) R.sub.9 -Cyc-Phe-COO-Cyc-Q (1rc) R.sub.9 -Cyc-Phe-COO-Phe-Q (1rd) R.sub.9 -Phe-Cyc-COO-Cyc-Q (1re) R.sub.9 -Phe-Cyc-COO-Phe-Q (1rf) R.sub.9 -Phe-Phe-COO-Cyc-Q (1rg) R.sub.9 -Phe-Phe-COO-Phe-Q (1rh) ______________________________________ Among these compounds, particularly the compounds expressed by formula (1rb), (1rc), or (1rd) are preferable. |
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