Isothiocyanatoethynylbenzene derivatives

A compound of formula N

• in which:
• R1 denotes H, straight chain alkyl having 1 to 12 C atoms, alkenyl having 2 to 12 C atoms, or branched alkyl having 3 to 12 C atoms, in which one or more CH2-groups may be replaced by
• where one or more non adjacent CH2-groups may be replaced by O and/or S, and where one or more H atoms may be replaced by F;
• or denotes a group RP,
• RP denotes halogen, CN, NCS, RF, RF—O— or RF—S—, wherein
• RF denotes fluorinated alkyl having 1 to 9 C atoms or fluorinated alkenyl having 2 to 9 C atoms,
• Z11, Z12 identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —C≡C—C≡C— or a single bond,
• U1, U2, V1 and V2 identically or differently, denote —N═ or —CR0═,
• R0 denotes H, Cl, F, CF3, CHF2, or alkyl or alkyoxy each having 1 to 6 C atoms,
• denote a radical selected from the following groups:
• a) the group consisting of 1,4-phenylene, 1,4-naphthylene, 2,6-naphthylene, tetralin-5,8-diyl, and tetralin-2,6-diyl, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by RL,
• b) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, bicyclo[1.1.1]pentane-1,3-diyl, 4,4′-bicyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, and spiro[3.3]heptane-2,6-diyl, in which one or more non-adjacent CH2 groups may be replaced by —O— and/or —S— and in which one or more H atoms may be replaced by F or alkyl having 1 to 6 C atoms,
• c) the group consisting of thiophene-2,5-diyl, thieno[3,2-b]thiophene-2,5-diyl, and selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by RL,
• RL on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5 or straight-chain having 1 to 12 C atoms or branched having 3 to 12 C atoms, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, and
• n is 0, 1 or 2.

A process for the production of a compound of formula I, comprising converting a compound of formula N:

• into a compound of formula I:
• in which:
• R1 denotes H, straight chain alkyl having 1 to 12 C atoms, alkenyl having 2 to 12 C atoms, or branched alkyl having 3 to 12 C atoms, in which one or more CH2-groups may be replaced by
• where one or more non adjacent CH2-groups may be replaced by O and/or S, and where one or more H atoms may be replaced by F;
• or denotes a group RP,
• RP denotes halogen, CN, NCS, RF, RF—O— or RF—S—, wherein RF denotes fluorinated alkyl having 1 to 9 C atoms or fluorinated alkenyl having 2 to 9 C atoms,
• Z11, Z12 identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —C≡C—C≡C— or a single bond,
• U1, U2, V1 and V2 identically or differently, denote —N═ or —CR0═,
• R0 denotes H, Cl, F, CF3, CHF2, or alkyl or alkyoxy each having 1 to 6 C atoms,
• denote a radical selected from the following groups:
• a) the group consisting of 1,4-phenylene, 1,4-naphthylene, 2,6-naphthylene, tetralin-5,8-diyl, and tetralin-2,6-diyl, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by RL,
• b) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, bicyclo[1.1.1]pentane-1,3-diyl, 4,4′-bicyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, and spiro[3.3]heptane-2,6-diyl, in which one or more non-adjacent CH2 groups may be replaced by —O— and/or —S— and in which one or more H atoms may be replaced by F or alkyl having 1 to 6 C atoms,
• c) the group consisting of thiophene-2,5-diyl, thieno[3,2-b]thiophene-2,5-diyl, and selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by RL,
• RL on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5 or straight-chain having 1 to 12 C atoms or branched having 3 to 12 C atoms, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, and
• n is 0, 1 or 2.