Patent ID: 6485797
Filing Date: 2002-11-26
Classification: C07C,C07D,C09K

Abstract:
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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”Oâ€”COâ€”Oâ€” or â€”Si(CH3)2â€” and/or b2) one or more â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€” and/or b2) one or two â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€” 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 â€”(CH2)4â€” or â€”(CH2)5â€” 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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€” or â€”Oâ€”COâ€” and/or b2) one or more â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€” or â€”Câ‰¡Câ€” 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 â€”CFâ€” or â€”CHâ€”; with the proviso that at least one of Y1, Y2 and Y3 is â€”Nâ€” or â€”CFâ€”; M1, M2, M3, independently of one another, are â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”CH2â€”Oâ€”, â€”Oâ€”CH2â€”, â€”CH2â€”CH2â€”, â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”; â€”CH2â€”CH2â€”COâ€”Oâ€”, â€”Oâ€”COâ€”CH2â€”CH2â€” 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 â€”Nâ€”, â€”CFâ€” or â€”CHâ€”, with the following provisos: if E1 (E4) is â€”Nâ€” or â€”CFâ€”, E2 and E3 (E5 and E6) must be â€”CHâ€”, if E2 and/or E3 (E5 and/or E6) are â€”CFâ€”, E1 (E4) must be â€”CHâ€”; if E2 (E5) is â€”Nâ€”, E1 (E4) must be â€”CHâ€”, while E3 (E5) can be â€”CHâ€” or â€”CFâ€”; and at least one of E1 to E6 must be â€”Nâ€” or â€”CFâ€”; G is â€”CH2CH2â€” or â€”CHâ€”CHâ€”; R1 and R2, independently of one another, are (a) a hydrogen atom, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”Oâ€”COâ€”Oâ€” or â€”Si(CH3)2â€” and/or b2) one or more â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€” and/or b2) one or two â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€” 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 â€”(CH2)4â€” or â€”(CH2)5â€” if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system; M1, M2, independently of one another, are â€”COâ€”O, â€”Oâ€”COâ€”, â€”CH2Oâ€”, â€”Oâ€”CH2, â€”CH2â€”CH2â€”, â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, â€”CH2â€”CH2â€”COâ€”Oâ€”, â€”Oâ€”COâ€”CH2â€”CH2â€” 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”Oâ€”COâ€”Oâ€” or â€”Si(CH3)2â€” and/or b2) one or more â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€” and/or b2) one or two â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€” 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 â€”(CH2)4â€” or â€”(CH2)5â€” if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system; M1, M2, M3, M4, independently of one another, are â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”CH2â€”Oâ€”, â€”Oâ€”CH2â€”, â€”CH2â€”CH2â€”, â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, â€”CH2â€”CH2â€”COâ€”Oâ€”, â€”Oâ€”COâ€”CH2CH2â€” 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€”â€”Oâ€”COâ€”, â€”Oâ€”COâ€”Oâ€” or â€”Si(CH3)2â€” and/or b2) one or more â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€” and/or b2) one or two â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€” 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 â€”(CH2)4â€” or â€”(CH2)5â€” 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 â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”CH2â€”Oâ€”, â€”Oâ€”CH2, â€”CH2â€”CH2â€”, â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, â€”CH2â€”CH2â€”COâ€”Oâ€”, â€”Oâ€”COâ€”CH2CH2â€” 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) â€”F, â€”Cl, â€”Br, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€” or â€”Oâ€”COâ€” 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”Oâ€”COâ€”Oâ€” or â€”Si(CH3)2â€” and/or b2) one or more â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”OCF3 if X3 is â€”F, â€”Cl, â€”Br, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€” and/or b2) one or two â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€” 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 â€”(CH2)4â€” or â€”(CH2)5â€” if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system; M1, M2, M3, independently of one another, are â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”CH2â€”Oâ€”, â€”Oâ€”CH2â€”, â€”CH2â€”CH2â€”, â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, â€”CH2CH2â€”COâ€”Oâ€”, â€”Oâ€”COâ€”CH2CH2â€” 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, â€”F, â€”Cl, â€”CN, â€”CF3 orâ€”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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”CO, â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”Oâ€”COâ€”Oâ€” or â€”Si(CH3)2â€” and/or b2) one or more â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€” and/or b2) one or to â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€” 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 â€”(CH2)4â€” or â€”(CH2)5â€” if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system; X1, X2, X3, independently of one another, are â€”CFâ€”, â€”Nâ€” or â€”CHâ€”; M1, M2, independently of one another, are â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”CH2â€”Oâ€”, â€”Oâ€”CH2â€”, â€”CH2â€”CH2â€”, â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, â€”CH2â€”CH2â€”COâ€”Oâ€”, â€”Oâ€”COâ€”CH2â€”CH2â€” 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, â€”F, â€”Cl, â€”CN, â€”CF3 or â€”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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”Oâ€”COâ€”Oâ€” or â€”Si(CH3)2â€” and/or b2) one or more â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, 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 â€”CH2â€” groups may be replaced by â€”Oâ€”, â€”Sâ€”, â€”COâ€”, â€”COâ€”Oâ€”, â€”Oâ€”COâ€” or â€”Si(CH3)2â€” and/or a2) one or two â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€” 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 â€”CH2â€” groups may be replaced by â€”Oâ€” and/or b2) one or two â€”CH2â€” groups may be replaced by â€”CH&boxH;CHâ€” 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 â€”(CH2)4â€” or â€”(CH2)5â€” if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyrane, butyrolactone or valerolactone system; M1, M2, independently of one another, are â€”COâ€”Oâ€”, â€”Oâ€”COâ€”, â€”CH2â€”Oâ€”, â€”Oâ€”CH2â€”, â€”CH2â€”CH2â€”, â€”CH&boxH;CHâ€”, â€”Câ‰¡Câ€”, â€”CH2â€”CH2â€”COâ€”Oâ€”, â€”Oâ€”COâ€”CH2â€”CH2â€” 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.