S-indacene and indeno[5,6-d][1,3]dioxol-derivatives and use thereof as components of liquid-crystal mixtures
AssigneeMerck Patent GmbH
InventorsLars Lietzau, Detlef Pauluth, Markus Czanta
Life of this patent
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Abstract
The invention relates 1,2,3,6,7,8-hexahydro-s-indacene derivatives and 6,7-dihydro-5H-indeno[5,6-d]-1,3-dioxole derivatives, and to the use thereof as component(s) in liquid-crystalline media. In addition, the present invention relates to liquid-crystal and electro-optical display elements which contain the liquid-crystalline media according to the invention.
Claims14
1,2,3,6,7,8-Hexahydro-s-indacene and 6,7-dihydro-5H-indeno-[5,6-d]-1,3-dioxole derivatives of the general formula I
- in which
- R1 denotes H, halogen, a linear or branched alkyl radical having 1 to 15 C atoms which is unsubstituted, monosubstituted by CN or CF3 or at least monosubstituted by halogen and in which one or more CH2 groups may each, independently of one another, be replaced by —O—, —S—, —CO—, —(CO)O—, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C— in such a way that heteroatoms are not linked directly to one another and asymmetrical groups may be present in both orientations,
- A1 in each case, independently of one another, identically or differently, denotes
- a) trans-1,4-cyclohexylene, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —S—, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl,
- b) 1,4-phenylene, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by halogen,
- c) a radical from the group 1,4-bicyclo[2.2.2]octylene, spiro[3.3]heptane-2,6-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, in which, in addition, CH may be replaced by N and in which, in addition, one or more H atoms may be replaced by halogen, or
- d) 1,4-cyclohexenylene,
- X denotes —CH2—, —CF2— or —O—,
- Y denotes F, Cl, CF3, CN, NCS, SCN, SF5 or 2- to 6-C perfluoroalkyl,
- in each case, independently of one another, in the case of asymmetrical bridging units Z1 in either of the two orientations, denotes a single bond, —CH2O—, —(CO)O—, —CF2O—, —CF═CF—, —CH2CH2CF2O—, —CF2CF2—, —CH2CF2—, —CH2CH2—, —CH═CH—, —CH═CF— or —C≡C—, and
- n denotes 0, 1, 2 or 3.
Compounds according to one or more of the preceding claims, characterised in that R1 denotes H, a linear alkyl or alkoxy radical having 1 to 12 C atoms or a linear alkenyl or alkenyloxy radical having 2 to 12 C atoms.
Use of compounds of the formula I according to one or more of the preceding claims as component(s) in liquid-crystalline media.
Liquid-crystalline medium having at least two liquid-crystalline components, characterised in that it comprises at least one 1,2,3,6,7,8-hexahydro-s-indacene or 6,7-dihydro-5H-indeno[5,6-d]-1,3-dioxole derivative according to one or more of the preceding claims.
Process for the preparation of compounds of the formula I according to one or more of the preceding claims, characterised in that it comprises one or more process steps by means of which a cyclopentane ring is connected in the 5,6-position to a 5,6-dibromo or 5,6-dihydroxy derivative of indane or of benzo-1,3-dioxole.
Dependencies are inferred from the claim text.