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US 12,359,128 B2Granted
Heteroaromatic isothiocyanates
AssigneeMerck Patent GmbH
InventorsConstanze Brocke, Dagmar Klass, Carsten Fritsch, Amir Hossain Parham
Life of this patent
Estimating the term…
Abstract
Heteroaromatic isothiocyanates of formula N wherein RN, AN1, AN2, ZN1, ZN2, W, X1, X2, and n are as defined herein can be used in liquid crystalline media. Liquid-crystalline media comprising one or more compounds of formula N are suitable for use in high-frequency components, especially microwave components for high-frequency devices, such as devices for shifting the phase of microwaves, tunable filters, tunable metamaterial structures, and electronic beam steering antennas, e.g., phased array antennas.
Claims17
A liquid-crystal medium comprising:
- one or more compounds of formula N
- in which
- RN denotes H, alkyl or alkoxy having 1 to 12 C atoms, or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12 C atoms, in which one or more CH2-groups may be replaced by,
- 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,
- ZN1 and ZN2, identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —C≡C—C≡C—, or a single bond,
- W denotes N, C—F or C—Cl,
- X1 and X2, identically or differently, denote H, Cl, F, methyl, or ethyl,
- on each occurrence, identically or differently, denote a radical selected from:
- a) the group consisting of 1,4-phenylene, 1,4-naphthylene, and 2,6-naphthylene, in which one or two CH groups may each be replaced by N and in which one or more H atoms may each be replaced by L,
- 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 each be replaced by —O— or —S— and in which one or more H atoms may each be replaced by F, and
- 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 be mono- or polysubstituted by L,
- L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5, or straight-chain, in each case optionally fluorinated, alkyl having 1 to 12 C atoms, alkoxy having 1 to 12 C atoms, alkylcarbonyl having 2 to 12 C atoms, alkoxycarbonyl having 2 to 12 C atoms, alkylcarbonyloxy having 2 to 12 C atoms, or alkoxycarbonyloxy having 2 to 12 C atoms, or branched, in each case optionally fluorinated, alkyl having 3 to 12 C atoms, alkoxy having 3 to 12 C atoms, alkylcarbonyl having 4 to 12 C atoms, alkoxycarbonyl having 4 to 12 C atoms, alkylcarbonyloxy having 4 to 12 C atoms, or alkoxycarbonyloxy having h to 12 C atoms, and
- n is 0, 1 or 2;
- and
- one or more compounds selected from the group of compounds consisting of the compounds of formulae I, II and III,
- in which
- R1 denotes H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH2-groups may each be replaced by,
- n is 0, 1 or 2,
- on each occurrence, independently of one another, denote
- in which RL, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms,
- and wherein
- alternatively denotes
- R2 denotes H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH2-groups may each be replaced by,
- Z21 denotes trans-CH═CH—, trans-CF═CF— or —C≡C—, and
- independently of one another, denote
- in which RL, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms;
- R3 denotes H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH2-groups may each be replaced by,
- one of Z31 and Z32, denotes trans-CH═CH—, trans-CF═CF—, or —C≡C— and the other one, independently thereof, denotes —C≡C—, trans-CH═CH—, trans-CF═CF—, or a single bond, and
- independently of one another, denote
- in which RL, on each occurrence identically or differently,
- denotes H or alkyl having 1 to 6 C atoms,
- and wherein
- alternatively denotes
31 more elements
Dependencies are inferred from the claim text.