# US 5,702,641 A · Liquid crystalline compound containing fluorine atom substituted alkyl group(s) and a liquid crystal composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,702,641 A - Document ID: US5702641A - Status: Granted - Kind: A - Application number: 08/576,461 - Filed: 1995-12-21 - Granted: 1997-12-30 - Earliest claimed: 1994-12-22 - Assignees: Chisso Corporation - Inventors: Yasuhiro Haseba; Kazutoshi Miyazawa; Shuichi Matsui; Tomoyuki Kondo; Yasuyuki Goto; Etsuo Nakagawa; Shinichi Sawada - Web page: https://patentgrep.com/patent/US5702641A ## CPC - C07C 43/225: containing halogen - C07C 22/08: containing fluorine - C07C 25/18: Polycyclic aromatic halogenated hydrocarbons - C09K 19/0403: {the structure containing one or more specific, optionally substituted ring or ring systems} - C09K 19/3001: {Cyclohexane rings} - C09K 19/3003: {Compounds containing at least two rings in which the different rings are directly linked (covalent bond)} - C09K 19/3028: {in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds} - C09K 19/42: Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 - C09K 19/46: containing esters - C09K 2019/0407: {containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone} - C09K 2019/0444: {characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group} - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract A liquid crystalline compound exhibiting a large .DELTA..epsilon. value, an electrical and chemical stability and a superior compatibility with existing liquid crystalline compounds, a liquid crystal composition containing the same, and a liquid crystal display element constructed by using the composition are provided, which liquid crystalline compound is expressed by the formula (I), F--(CH.sub.2)n-E--(CH.sub.2 CH.sub.2).sub.k --G--(CH.sub.2 CH.sub.2).sub.l --L--(CH.sub.2 CH.sub.2).sub.m --Z--Q--Y (I) wherein n is an integer of 1 to 10; k, l and m each independently are an integer of 0 to 2; ring E is 1,4-cyclohexylene group or 1,4-phenylene group, wherein one or more H atoms on each six-membered ring may be replaced by F atom(s); G and L each independently is a covalent bond or 1,4-cyclohexylene group or 1,4-phenylene group, wherein one or more H atoms on each six-membered ring may be replaced by F atom(s); Q is covalent bond or --O--; Y is a fluoroalkyl group of 1 to 3C or F atom; but in the case where ring E is 1,4-cyclohexylene group and at least one of G and L is covalent bond, k+l+m.noteq.0, and in the case where Q is --O--, Y is not F atom. ## Claims ### Claim 1 A liquid crystalline compound expressed by the formula (I): F--(CH.sub.2)n-E--(CH.sub.2 CH.sub.2).sub.k --G--(CH.sub.2 CH.sub.2).sub.m --L--(CH.sub.2 CH.sub.2).sub.m --Z--Q--Y (I) wherein n represents an integer of 1 to 10; k, l and m each independently represent an integer of 0 to 2; E represents 1,4-cyclohexylene group or 1,4-phenylene group wherein one or more hydrogen atoms on a six-membered ring may be replaced by fluorine atom(s); G and L each independently represent a covalent bond or 1,4-cyclohexylene group or 1,4-phenylene group wherein one or more hydrogen atoms may be replaced by fluorine atom(s), provided that when only one of G or L is a covalent bond, G is the covalent bond; Z represents 1,4-phenylene group wherein one or more hydrogen atoms on the 1,4-phenylene group may be replaced by fluorine atom(s); Q represents a covalent bond or --O--; Y represents a fluoroalkyl group of 1 to 3 carbon atoms or fluorine atom; and when E represents 1,4-cyclohexylene group and at least one of G and L represents a covalent bond, k+l+m.noteq.0 and when Q represents --O--, Y does not represent fluorine atom. ### Claim 2 (depends on 1) A liquid crystalline compound according to claim 1, wherein k, l and m each independently represent 0 or 1, and E represents 1,4-phenylene group or fluorine-substituted 1,4-phenylene group. ### Claim 3 (depends on 1) A liquid crystalline compound according to claim 1, wherein k, l and m each independently represent 0 or 1 and E represents 1,4-cyclohexylene group. ### Claim 4 (depends on 3) A liquid crystalline compound according to claim 3, wherein k, l and m each are zero; G represents a covalent bond; and L represents 1,4-cyclohexylene group, 1,4-phenylene group or fluorine-substituted 1,4-phenylene group. ### Claim 5 (depends on 4) A liquid crystalline compound according to claim 4, wherein L represents 1,4-cyclohexylene group. ### Claim 6 (depends on 4) A liquid crystalline compound according to claim 4, wherein L represents 1,4-phenylene group or fluorine-substituted 1,4-phenylene group. ### Claim 7 (depends on 3) A liquid crystalline compound according to claim 3, wherein k and l each represent 0; m represents 1; G represents a covalent bond; and L represents 1,4-cyclohexylene group, 1,4-phenylene group or fluorine-substituted 1,4-phenylene group. ### Claim 8 (depends on 7) A liquid crystalline compound according to claim 7, wherein L represents 1,4-cyclohexylene group. ### Claim 9 (depends on 7) A liquid crystalline compound according to claim 7, wherein L represents 1,4-phenylene group or fluorine-substituted 1,4-phenylene group. ### Claim 10 (depends on 3) A liquid crystalline compound according to claim 3, wherein k represents 1; l and m each represent 0; and G and L each represent a covalent bond. ### Claim 11 (depends on 1) A liquid crystalline compound according to claim 1, wherein G and L each independently represent 1,4-cyclohexylene group, 1,4-phenylene group or fluorine-substituted phenylene group. ### Claim 12 A liquid crystalline compound expressed by the formula (I): F--(CH.sub.2)n-E(CH.sub.2 CH.sub.2).sub.k --G--(CH.sub.2 CH.sub.2).sub.l --L--(CH.sub.2 CH.sub.2).sub.m --Z--Q--Y (I) wherein n represents an integer of 1 to 10; k and m each represent the integer 1, and l represents 0; E represents 1,4-cyclohexylene group wherein one or more hydrogen atoms on the cyclohexylene ring may be replaced by fluorine atom(s); G represents a covalent bond; L represents 1,4-cyclohexylene group wherein one or more hydrogen atoms on the cyclohexylene ring may be replaced by fluorine atom(s), or L represents fluorine-substituted 1,4-phenylene group; Z represents 1,4-phenylene group wherein one or more hydrogen atoms on the 1,4-phenylene group may be replaced by fluorine atom(s); Q represents a covalent bond or --O--; Y represents a fluoroalkyl group of 1 to 3 carbon atoms or fluorine atom; k+l+m.noteq.0; and when Q represents --O--, Y does not represent fluorine atom. ### Claim 13 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) A liquid crystal composition containing at least one of liquid crystalline compounds according to one of claim 2 to 9, 10, 11, 1 or 12. ### Claim 14 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) A liquid crystal composition containing at least one member of the liquid crystalline compounds set forth in one of claims 2 to 9, 10, 11, 1 or 12, as a first component, and at least one member of compounds selected from the group consisting of compounds expressed by the following formulas (II), (III) and (IV), as a second component: ##STR420## wherein R.sub.1 represents an alkyl group of 1 to 10 carbon atoms; V represents F, Cl, CF.sub.3, OCF.sub.3, OCF.sub.2 H or an alkyl group of 1 to 10 carbon atoms; L.sub.1, L.sub.2, L.sub.3 and L.sub.4 each independently represent H or F; Z.sub.1 and Z.sub.2 each independently represent --(CH.sub.2).sub.2 --, --CH.dbd.CH-- or a covalent bond; ring A represents trans-1,4-cyclohexylene group or 1,4-phenylene group; a represents 1 or 2; and b represents 0 or 1. ### Claim 15 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11) A liquid crystal composition containing at least one member of the liquid crystalline compounds set forth in one of claims 2 to 9, 10, 11, 1, or 12, as a first component, and at least one member of compounds selected from the group consisting of compounds expressed by the following formulas (V), (VI), (VII), (VIII) and (IX), as a second component: ##STR421## wherein R.sub.2 represents F, an alkyl group of 1 to 10 carbon atoms or an alkenyl group of 2 to 10 carbon atoms, and in either of the groups, an optional methylene group (--CH.sub.2 --) in the groups may be replaced by oxygen atom (--O--), but two or more methylene groups therein are not continuously replaced by oxygen atom; Z.sub.3 represents --(CH.sub.2).sub.2 --, --COO or a covalent bond; L.sub.5 and L.sub.6 each independently represent H or F; D.sub.1 represents trans-1,4-cyclohexylene group, 1,4-phenylene group or 1,3-dioxane-2,5-diyl group; ring U represents trans-1,4-cyclohexylene group or 1,4-phenylene group; and c and d each independently represent 0 or 1, ##STR422## wherein R.sub.3 represents an alkyl group of 1 to 10 carbon atoms; L.sub.7 represents H or F; and e represents 0 or 1, ##STR423## wherein R.sub.4 represents an alkyl group of 1 to 10 carbon atoms; I represents trans-1,4-cyclohexylene group or 1,4-phenylene group; L.sub.8 and L.sub.9 each independently represent H or F; Z.sub.4 represents --COO-- or a covalent bond; Z.sub.5 represents --COO-- or --C.tbd.C--; and f and g each independently represent 0 or 1, R.sub.5 --W--Z.sub.6 --K--R.sub.6 (VIII) wherein R.sub.5 and R.sub.6 each independently represent an alkyl group, an alkoxy group or an alkoxymethyl group, each of 1 to 10 carbon atoms; W represents trans-1,4-cyclohexylene group, 1,4-phenylene group or 1,3-pyrimidine-2,5-diyl group; K represents trans-1,4-cyclohexylene group or 1,4-phenylene group; and Z.sub.6 represents --C.tbd.C--, --COO--, --(CH.sub.2).sub.2 -- or a covalent bond, ##STR424## wherein R.sub.7 represents an alkyl group or an alkoxy group each of 1 to 10 carbon atoms; R.sub.8 represents an alkyl group of 1 to 10 carbon atoms, and an optional methylene group (--CH.sub.2 --) in R.sub.8 may be replaced by oxygen atom (--O--), but two or more methylene groups are not continuously replaced by oxygen atom (--O--); M, represents trans-1,4-cyclohexylene group or 1,3-pyrimidine-2,5-diyl group; rings N and P each independently represent trans-1,4-cyclohexylene group or 1,4-phenylene group; Z.sub.7 represents --COO--, --(CH.sub.2).sub.2 --, --CH.dbd.CH-- or a covalent bond; Z.sub.8 represents --C.tbd.C--, --COO-- or a covalent bond; h represents 0 or 1; and L.sub.10 represents H or F. ### Claim 16 (depends on 13) A liquid crystal display element comprising the liquid crystal composition set forth in claim 13. ### Claim 17 (depends on 14) A liquid crystal display element comprising the liquid crystal composition set forth in claim 14. ### Claim 18 (depends on 15) A liquid crystal display element comprising the liquid crystal composition set forth in claim 15. ### Claim 19 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11) A liquid crystal composition containing at least one member of the liquid crystalline compounds set forth in one of claims 2 to 9, 10, 11, 1, or 12, as a first component, and at least one member of compounds selected from the group consisting of compounds expressed by the formulas (II), (III) and (IV), as a part of the second component, and at least one member of compounds selected from the group consisting of compounds expressed by the formulas (V), (VI), (VII), (VIII) and (IX), as another part of the second component, ##STR425## wherein R.sub.1 represents an alkyl group of 1 to 10 carbon atoms; V represents F, Cl, CF.sub.3, OCF.sub.3, OCF.sub.2 H or an alkyl group of 1 to 10 carbon atoms; L.sub.1, L.sub.2, L.sub.3 and L.sub.4 each independently represent H or F; Z.sub.1 and Z.sub.2 each independently represent --(CH.sub.2).sub.2 --, --CH.dbd.CH-- or a covalent bond; ring A represents trans-1,4-cyclohexylene group or 1,4-phenylene group; a represents 1 or 2; and b represents 0 or 1, ##STR426## wherein R.sub.2 represents F, an alkyl group of 1 to 10 carbon atoms or an alkenyl group of 2 to 10 carbon atoms, and in either of the groups, an optional methylene group (--CH.sub.2 --) in the groups may be replaced by oxygen atom (--O--), but two or more methylene groups therein are not continuously replaced by oxygen atom; Z.sub.3 represents --(CH.sub.2).sub.2 --, --COO-- or a covalent bond; L.sub.5 and L.sub.6 each independently represent H or F; D.sub.1 represents trans-1,4-cyclohexylene group, 1,4-phenylene group or 1,3-dioxane-2,5-diyl group; ring U represents trans-1,4-cyclohexylene group or 1,4-phenylene group; and c and d each independently represent 0 or 1, ##STR427## wherein R.sub.3 represents an alkyl group of 1 to 10 carbon atoms; L.sub.7 represents H or F; and e represents 0 or 1, ##STR428## wherein R.sub.4 represents an alkyl group of 1 to 10 carbon atoms; I represents trans-1,4-cyclohexylene group or 1,4-phenylene group; L.sub.8 and L.sub.9 each independently represent H or F; Z.sub.4 represents --COO-- or a covalent bond; Z.sub.5 represents --COO-- or --C.tbd.C--; and f and g each independently represent 0 or 1, R.sub.5 --W--Z.sub.6 --K--R.sub.6 (VIII) wherein R.sub.5 and R.sub.6 each independently represent an alkyl group, an alkoxy group or an alkoxymethyl group, each of 1 to 10 carbon atoms; W represents trans-1,4-cyclohexylene group, 1,4-phenylene group or 1,3-pyrimidine-2,5-diyl group; K represents trans-1,4-cyclohexylene group or 1,4-phenylene group; and Z.sub.6 represents --C.tbd.C--, --COO--, --(CH.sub.2).sub.2 -- or a covalent bond, ##STR429## wherein R.sub.7 represents an alkyl group or an alkoxy group each of 1 to 10 carbon atoms; R.sub.8 represents an alkyl group of 1 to 10 carbon atoms, and an optional methylene group (--CH.sub.2 --) in R.sub.8 may be replaced by oxygen atom (--O--), but two or more methylene groups are not continuously replaced by oxygen atom (--O--); M represents trans-1,4-cyclohexylene group or 1,3-pyrimidine-2,5-diyl group; rings N and P each independently represent trans-1,4-cyclohexylene group or 1,4-phenylene group; Z.sub.7 represents --COO--, --(CH.sub.2).sub.2 --, --CH.dbd.CH-- or a covalent bond; Z.sub.8 represents --C.tbd.C--, --COO-- or a covalent bond; h represents 0 or 1; and L.sub.10 represents H or F. ### Claim 20 (depends on 19) A liquid crystal display element comprising the liquid crystal composition set forth in claim 19.