5-Arylindane derivatives and ferroelectric liquid crystal mixture containing same

A ferroelectric liquid crystal mixture comprising a compound of group A:

• A. 5-arylindane derivatives of the formula (I),
• wherein the symbols and indices have the following meanings,
• R1 and R2, independently of one another, are
• (a) a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3,
• (b) a straight-chain or branched-chain alkyl group (with or Without an asymmetric carbon atom) having from 1 to 20 carbon atoms, in which
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or —Si(CH3)2— and/or
• b2) one or more —CH2— groups may be replaced by —CH═CH—, —C≡C—, 1,4-cyclohexylene, 1,4-phenylene, cyclopropane-1,2-diyl or 1,3-cyclopentylene and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or
• b4) the terminal CH3-group may be replaced by any one of the following chiral groups (optically active or racemic):
• with the proviso that only one of R1, R2 can be a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3;
• R3, R4, R5, R6, R7, independently of one another, are
• a) a hydrogen atom,
• b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 16 carbon atoms, where
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O— and/or
• b2) one or two —CH2— groups may be replaced by —CH═CH— and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F or Cl,
• c) R4 and R5 may also together be —(CH2)4— or —(CH2)5— if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system;
• R8 is
• a) a hydrogen atom, a halogen atom or CN
• b) a straight-chain or branched-chain alkyl group (with or without asymmetric carbon atoms) having from 1 to 16 carbon atoms, where
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O— or —O—CO— and/or
• b2) one or more —CH2— groups may be replaced by —CH═CH— or —C≡C— and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl;
• Y1, Y2 and Y3, independently of one another, are —CF— or —CH—;
• with the proviso that at least one of Y1, Y2 and Y3 is —N— or —CF—;
• M1, M2, M3, independently of one another, are
• —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CH2—CH2—, —CH═CH—, —C≡C—;
• —CH2—CH2—CO—O—, —O—CO—CH2—CH2— or a single bond;
• A1, A2, A3, independently of one another, are
• 1,4-phenylene, in which one or more H atoms may be replaced by F, Cl and/or CN, pyridine-2,5-diyl, in which one H atom may be replaced by F, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, in which one H atom may be replaced by F, pyridazin-3,6-diyl, in which one H atom may be replaced by F, 1,4-cyclohexylene, in which one or two hydrogen atoms may be substituted by CN and/or F and/or CH3, naphthalene-2,6-diyl, in which one or more H atoms may be replaced by F, Cl and/or CN, thiophene-2,5-diyl, in which one or two H atoms may be replaced by F, [1,1,3,4]-thiadiazole-2,5-diyl, [1,3]-thiazole-2,4-diyl, in which one H atom may be replaced by F, [1,3]-thiazole-2,5-diyl, in which one H atom may be replaced by F, or 1,3-dioxane-2,5-diyl;
• a, b, c are 0 or 1 with the proviso, that compounds of the formula (I) do not contain more than four five- or six-membered ring systems;
• and a further compound of any of the groups B to G:
• B. phenanthrene derivatives of the formula (II)
• in which the symbols and indices have the following meanings:
• E1, E2, E3, E4, E5 and E6 are —N—, —CF— or —CH—, with the following provisos:
• if E1 (E4) is —N— or —CF—, E2 and E3 (E5 and E6) must be —CH—,
• if E2 and/or E3 (E5 and/or E6) are —CF—, E1 (E4) must be —CH—;
• if E2 (E5) is —N—, E1 (E4) must be —CH—, while E3 (E5) can be —CH— or —CF—;
• and at least one of E1 to E6 must be —N— or —CF—;
• G is —CH2CH2— or —CH—CH—;
• R1 and R2, independently of one another, are
• (a) a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3,
• (b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 20 carbon atoms, in which
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or —Si(CH3)2— and/or
• b2) one or more —CH2— groups may be replaced by —CH═CH—, —C≡C—, 1,4-cyclohexylene, 1,4-phenylene, cyclopropane-1,2-diyl or 1,3-cyclopentylene and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or
• b4) the terminal CH3-group may be replaced by any one of the following chiral groups (optically active or racemic):
• with the proviso that only one of R1, R2 can be a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3;
• R3, R4, R5, R6, R7, independently of one another, are
• a) a hydrogen atom,
• b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 16 carbon atoms, where
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O— and/or
• b2) one or two —CH2— groups may be replaced by —CH═CH— and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F or Cl,
• c) R4 and R5 may also together be —(CH2)4— or —(CH2)5— if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system;
• M1, M2, independently of one another, are
• —CO—O, —O—CO—, —CH2O—, —O—CH2, —CH2—CH2—, —CH═CH—, —C≡C—,
• —CH2—CH2—CO—O—, —O—CO—CH2—CH2— or a single bond;
• A1, A2, independently of one another, are
• 1,4-phenylene, in which one or more H atoms may be replaced by F, Cl and/or CN, pyridine-2,5-diyl, in which one H atom may be replaced by F, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, in which one H atom may be replaced by F, pyridazin-3,6-diyl, in which one H atom may be replaced by F, 1,4-cyclohexylene in which one or two hydrogen atoms may be substituted by CN and/or F and/or CH3, thiophene-2,5-diyl, [1,3,4]-thiadiazole-2,5-diyl, [1,31]-thiazole-2,4-diyl, [1,3]-thiazole-2,5-diyl or 1,3-dioxane-2,5-diyl;
• a, b are 0 or 1 with the proviso, that compounds of the formula (II) do not contain more than three five- or six-membered ring systems;
• C. 2-fluoropyridine derivatives of the formula (III),
• in which the symbols and indices have the following meanings:
• R1 and R21 independently of one another, are
• (a) a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3,
• (b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 20 carbon atoms, in which
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or —Si(CH3)2— and/or
• b2) one or more —CH2— groups may be replaced by —CH═CH—, —C≡C—, 1,4-cyclohexylene, 1,4-phenylene, cyclopropane-1,2-diyl or 1,3-cyclopentylene and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or
• b4) the terminal CH3-group may be replaced by any one of the following chiral groups (optically active or racemic):
• with the proviso that only one of R1, R2 can be a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3;
• R3, R4, R5, R6, R7, independently of one another, are
• a) a hydrogen atom,
• b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 16 carbon atoms, where
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O— and/or
• b2) one or two —CH2— groups may be replaced by —CH═CH— and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F or Cl,
• c) R4 and R6 may also together be —(CH2)4— or —(CH2)5— if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system;
• M1, M2, M3, M4, independently of one another, are
• —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CH2—CH2—, —CH═CH—, —C≡C—, —CH2—CH2—CO—O—, —O—CO—CH2CH2— or a single bond;
• A1, A2, A3, A41 independently of one another, are
• 1,4phenylene, in which one or more H atoms may be replaced by F, Cl and/or CN, pyridine-2,5-diyl, in which one H atom may be replaced by F, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, in which one H atom may be replaced by F, pyridazin-3,6-diyl, in which one H atom may be replaced by F, 1,4-cyclohexylene in which one or two hydrogen atoms may be substituted by CN and/or F and/or CH3, naphthalene-2,6-diyl in which one or more H atoms may be replaced by F, Cl and/or CN, thiophene-2,5-diyl, [1,3,4]-thiadiazole-2,5-diyl, [1,3]-thiazole-2,4-diyl, [1,31]-thiazole-2,5-diyl or 1,3-dioxane-2,5-diyl;
• a, b, c, d are 0 or 1 with the proviso, that compounds of the formula (III) do not contain more than four five or six-membered ring systems;
• D. phenylene derivatives of the formula (IV),
• in which the symbols and indices have the following meanings:
• R1 and R2, independently of one another, are
• (a) a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3,
• (by a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 20 carbon atoms, in which
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O——O—CO—, —O—CO—O— or —Si(CH3)2— and/or
• b2) one or more —CH2— groups may be replaced by —CH═CH—, —C≡C—, 1,4-cyclohexylene, 1,4-phenylene, cyclopropane-1,2-diyl or 1,3-cyclopentylene and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or
• b4) the terminal CH3-group may be replaced by any one of the following chiral groups (optically active or racemic):
• with the proviso that only one of R1, R2 can be a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF;
• R3, R4, R5, R6, R7, independently of one another, are
• a) a hydrogen atom,
• b) a straight-chain or branched chain alkyl group (with or without asymmetric carbon atoms) having from 1 to 16 carbon atoms, where
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O— and/or
• b2) one or two —CH2— groups may be replaced by —CH═CH— and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F or Cl,
• c) R4 and R5 may also together be —(CH2)4— or —(CH2)5— if they are bonded to an oxirane, dioxolane, tetrahydrofuran tetrahydropyrane, butyrolactone or valerolactone system;
• X1 and X2, independently of one another, are hydrogen, F, Cl, CF3 or CN, with the proviso that X1 and x2 are not simultaneously hydrogen;
• M1, M2, M3, M4, independently of one another, are
• —CO—O—, —O—CO—, —CH2—O—, —O—CH2, —CH2—CH2—, —CH═CH—, —C≡C—, —CH2—CH2—CO—O—, —O—CO—CH2CH2— or a single bond;
• A1, A2, A4, independently of one another, are
• 1,4-phenylene, in which one or more H atoms may be replaced by F, Cl and/or CN, pyridine-2,5-diyl, in which one H atom may be replaced by F, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, in which one H atom may be replaced by F, pyridazin-3,6-diyl, in which one H atom may be replaced by F, 1,4-cyclohexylene in which one or two hydrogen atoms may be substituted by CN and/or F and/or CH3, naphthalene-2,6-diyl in which one or more H atoms may be replaced by F, Cl and/or CN, 1,2,3,4-tetrahydronapthalene-2,6-diyl, thiophene-2,5-diyl, [3,4]-thiadiazole-2,5-diyl, [1,3]-thiazole-2,4-diyl, [1,3]-thiazole-2,5-diyl or 1,3-dioxane-2,5-diyl;
• a, b, c, d are 0 or 1 with the proviso, that compounds of the formula (IV) do not contain more than four five- or six-membered ring systems;
• E. meta-substituted aromatic compounds of the formula (V):
• wherein the symbols and indices have the following meanings:
• X3 is
• (a) —F, —Cl, —Br, —CN, —CF3 or —OCF3,
• (b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 12 carbon atoms, in which
• b1) one or two non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O— or —O—CO— and/or
• b2) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or CN;
• R1 is
• (a) a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3,
• (b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 20 carbon atoms, in which
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or —Si(CH3)2— and/or
• b2) one or more —CH2— groups may be replaced by —CH═CH—, —C≡C—, 1,4-cyclohexylene, 1,4-phenylene, cyclopropane-1,2-diyl or 1,3-cyclopentylene and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or
• b4) the terminal CH3-group may be replaced by any one of the following chiral groups (optically active or racemic):
• with the proviso that R1 can not be a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3 if X3 is —F, —Cl, —Br, —CN, —CF3 or —OCF3;
• R3, R4, R5, R6, R7, independently of one another, are
• a) a hydrogen atom,
• b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 16 carbon atoms, where
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O— and/or
• b2) one or two —CH2— groups may be replaced by —CH═CH— and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F or Cl,
• c) R4 and R5 may also together be —(CH2)4— or —(CH2)5— if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system;
• M1, M2, M3, independently of one another, are
• —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CH2—CH2—, —CH═CH—, —C≡C—, —CH2CH2—CO—O—, —O—CO—CH2CH2— or a single bond;
• A1, A2, A3, independently of one another, are
• 1,4-phenylene, in which one or more H atoms may be replaced by F, Cl and/or CN, pyridine-2,5-diyl, in which one H atom may be replaced by F, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, in which one H atom may be replaced by F, pyridazin-3,6-diyl, in which one H atom may be replaced by F, 1,4-cyclohexylene in which one or two hydrogen atoms may be substituted by CN and/or F and/or CH3, naphthalene-2,6-diyl in which one or more H atoms may be replaced by F, Cl and/or CN, thiophene-2,5-diyl, [1,3,4]-thiadiazole-2,5-diyl, [1,3]-thiazole-2,4-diyl, [1,3]-thiazole-2,5-diyl or 1,3-dioxane-2,5-diyl;
• a, b, c are 0 or 1 with the proviso, that compounds of the formula (V) do;
• not contain more than four five- or six-membered ring systems;
• F. (1,3,4)-thiadiazoles of the formula (I):
• wherein the symbols and indices have the following meanings:
• R1 and R2, independently of one another, are
• (a) a hydrogen atom, —F, —Cl, —CN, —CF3 or—OCF3,
• (b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 20 carbon atoms, in which
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO, —CO—O—, —O—CO—, —O—CO—O— or —Si(CH3)2— and/or
• b2) one or more —CH2— groups may be replaced by —CH═CH—, —C≡C—, 1,4-cyclohexylene, 1,4-phenylene, cyclopropane-1,2-diyl or 1,3-cyclopentylene and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or
• b4) the terminal CH3-group may be replaced by any one of the following chiral groups (optically active or racemic):
• with the proviso that only one of R1, R2 can be a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3;
• R3, R4, R5, R6, R7, independently of one another, are
• a) a hydrogen atom,
• b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 16 carbon atoms, where
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O— and/or
• b2) one or to —CH2— groups may be replaced by —CH═CH— and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F or Cl,
• c) R4 and R5 may also together be —(CH2)4— or —(CH2)5— if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system;
• X1, X2, X3, independently of one another, are —CF—, —N— or —CH—;
• M1, M2, independently of one another, are
• —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CH2—CH2—, —CH═CH—, —C≡C—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2— or a single bond;
• A1, A2, A3, independently of one another, are
• 1,4-phenylene, in which one or more H atoms may be replaced by F, Cl and/or CN, pyridine-2,5-diyl, in which one H atom may be replaced by F, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, in which one H atom may be replaced by F, pyridazin-3,6-diyl, in which one H atom may be replaced by F, 1,4-cyclohexylene in which one or two hydrogen atoms may be substituted by CN and/or F and/or CH3, naphthalene-2,6-diyl in which one or more H atoms may be replaced by F, Cl and/or CN, thiophene-2,5-diyl, [1,3,4]-thiadiazole-2,5-diyl, [1,31]-thiazole-2,4-diyl, [1,3]-thiazole-2,5-diyl or 1,3-dioxane-2,5-diyl;
• a, b, c are 0 or 1 with the proviso, that compounds of the formula (VI) do not contain more than four five- or, six-membered ring systems;
• G. 4-cyanocyclohexyls of the formula (VII):
• wherein the symbols and indices have the following meanings:
• R1 is
• (a) a hydrogen atom, —F, —Cl, —CN, —CF3 or —OCF3,
• (b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 20 carbon atoms, in which
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or —Si(CH3)2— and/or
• b2) one or more —CH2— groups may be replaced by —CH═CH—, —C≡C—, 1,4-cyclohexylene, 1,4-phenylene, cyclopropane-1,2-diyl or 1,3-cyclopentylene and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or
• b4) the terminal CH3group may be replaced by any one of the following chiral groups (optically active or racemic):
• R2 is
• (a) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom), having from 1 to 16 carbon atoms, in which
• a1) one or two non-adjacent and non-terminal —CH2— groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO— or —Si(CH3)2— and/or
• a2) one or two —CH2— groups may be replaced by —CH═CH—, —C≡C— and/or
• a3) one or more hydrogen atoms of the alkyl group may be substituted by F and/or Cl and/or CN and/or CF3;
• R3, R4, R5, R6, R7, independently of one another, are
• a) a hydrogen atom,
• b) a straight-chain or branched-chain alkyl group (with or without an asymmetric carbon atom) having from 1 to 16 carbon atoms, where
• b1) one or more non-adjacent and non-terminal —CH2— groups may be replaced by —O— and/or
• b2) one or two —CH2— groups may be replaced by —CH═CH— and/or
• b3) one or more hydrogen atoms of the alkyl group may be substituted by F or C,
• c) R4 and R5 may also together be —(CH2)4— or —(CH2)5— if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system;
• M1, M2, independently of one another, are
• —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CH2—CH2—, —CH═CH—, —C≡C—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2— or a single bond;
• A1, A2, independently of one another, are
• 1,4-phenylene, in which one or more H atoms may be replaced by F, Cl and/or CN, pyridine-2,5-diyl, in which one H atom may be replaced by F, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, in which one H atom may be replaced by F, pyridazin-3,6-diyl, in which one H atom may be replaced by F, 1,4-cyclohexylene in which one or two hydrogen atoms may be substituted by CN and/or F and/or CH3, naphthalene-2,6-diyl in which one or more H atoms may be replaced by F, Cl and/or CN, thiophene-2,5-diyl, [1,3,4]-thiadiazole-2,5-diyl, [1,3]-thiazole-2,4-diyl, [1,3]-thiazole-2,5-diyl or 1,3-dioxane-2,5-diyl;
• a, b are 0 or 1 with the proviso, that compounds of the formula (VII) do not contain more than four five- or six-membered ring systems.