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US 12,595,415 B2Granted
Aromatic isothiocyanates
AssigneeMerck Patent GmbH
InventorsConstanze Brocke, Dagmar Klass, Carsten Fritzsch
Life of this patent
Estimating the term…
Abstract
A compound of formula UI and a liquid crystal medium containing the compound of formula UI and high-frequency components containing such media, 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, for example, phased array antennas.
Claims20
A liquid crystal medium comprising
- one or more compounds of formula UI-1-3
- in which
- RU denotes H, straight-chain non-fluorinated alkyl having 1 to 12 C atoms, or branched non-fluorinated alkyl having 3 to 12 C atoms, or non-fluorinated alkenyl having 2 to 12 C atoms, in which one or more CH2-groups may be replaced by
- and in which one or more non-adjacent CH2-groups may be replaced by O, or denotes a group R″,
- RP denotes halogen, CN, NCS, fluorinated alkyl, RF—O- or RF—S—,
- RF denotes fluorinated alkyl having 1 to 9 C atoms or fluorinated alkenyl having 2 to 9 C atoms;
- and
- one or more compounds of formula UII
- in which
- RU denotes H, a straight-chain alkyl having 1 to 12 C atoms or branched alkyl having 3 to 12 C atoms or alkenyl having 2 to 12 C atoms, in which one or more CH2-groups may be replaced by
- and in which one or more non-adjacent CH2-groups may be replaced by O, or denotes a group RP,
- RP denotes halogen, CN, NCS, RF—, RF—O- or RF—S—,
- RF denotes fluorinated alkyl having 1 to 9 C atoms or fluorinated alkenyl having 2 to 9 C atoms,
- ZU1, ZU2 identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C═C—, —C═C—C═C- or a single bond,
- XU1, XU2, identically or differently, denote Cl or F,
- each independently denote:
- a) 1,4-phenylene, 1,4-naphthylene or 2,6-naphthylene, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by L,
- b) trans-1,4-cyclohexylene, 1,4-cyclohexenylene, tetralin-2,6-diyl, tetralin-5,8-diyl, decalin-2,6-diyl, bicyclo[1.1.1]pentane-1,3-diyl, 4,4′-bicyclohexylene, bicyclo[2.2.2]octane-1,4-diyl or spiro [3.3]heptane-2,6-diyl, in which one or two CH groups may be replaced by N, 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 L, or
- c) thiophene-2,5-diyl, thieno [3,2-b]thiophene-2,5-diyl or selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L,
- L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5 or a straight-chain, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy each having 1 to 12 C atoms, or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy each having 3 to 12 C atoms, and atoms, and
- u is 0, 1 or 2,
- from which the compounds of formula UI-1-3 are excluded,
- and
- one or more compounds selected from the group of compounds of formulae UI-1, UI-2 and UI-3
- from which compounds of formulae UI-1, the compounds
- of formula UI-1-3 are excluded
- in which
- RU denotes H, straight-chain non-fluorinated alkyl having 1 to 12 C atoms, or branched non-fluorinated alkyl having 3 to 12 C atoms, or non-fluorinated alkenyl having 2 to 12 C atoms, in which one or more CH2-groups may be replaced by
- and in which one or more non-adjacent CH2-groups may be replaced by O, or denotes a group RP,
- RP denotes halogen, CN, NCS, fluorinated alkyl, RF—O- or RF—S—,
- RF denotes fluorinated alkyl having 1 to 9 C atoms or fluorinated alkenyl having 2 to 9 C atoms;
- XU1, XU2 identically or differently, denote Cl or F,
- each independently denote:
- a) 1,4-phenylene, 1,4-naphthylene or 2,6-naphthylene, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by L,
- b) trans-1,4-cyclohexylene, 1,4-cyclohexenylene, tetralin-2,6-diyl, tetralin-5,8-diyl, decalin-2,6-diyl, bicyclo[1.1.1]pentane-1,3-diyl, 4,4′-bicyclohexylene, bicyclo[2.2.2]octane-1,4-diyl or spiro [3.3]heptane-2,6-diyl, in which one or two CH groups may be replaced by N, 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 L, or
- c) thiophene-2,5-diyl, thieno [3,2-b]thiophene-2,5-diyl or selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L,
- L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5 or a straight-chain, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy each having 1 to 12 C atoms, or a branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy each having 3 to 12 C atoms;
- with the proviso that in formula UI-3 at least one of
- and
- denotes trans-1,4-cyclohexylene, 1,4-cyclohexenylene, tetralin-2,6-diyl, tetralin-5,8-diyl, decalin-2,6-diyl, 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 two CH groups may be replaced by N, 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 L, wherein L, on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5 or a straight-chain, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy each having 1 to 12 C atoms or a branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkyl-carbonyloxy or alkoxycarbonyloxy each having 1 to 12 C atoms,
- wherein the medium contains the one or more compounds selected from the group of compounds of formulae UI-1, UI-2 and UI-3, the one or more compounds of formula UI-1-3 and the one or more compounds of formula UII in a total concentration of 15% to 50%;
- and
- one or more compounds of formula III-1b:
- 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 be replaced by
- and
- one or more compounds of formulae I, II and/or III, wherein from the compounds of formula III the compounds of formula III-1b are excluded:
- 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 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,
- or
- in which one or more H atoms may be replaced by alkyl having 1 to 6 C atoms or F,
- 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 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,
- or
- in which one or more H atoms may be replaced by alkyl having 1 to 6 C atoms or F,
- 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 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,
- or
- in which one or more H atoms may be replaced by alkyl having 1 to 6 C atoms or F,
- and wherein
- alternatively denotes
69 more elements
Dependencies are inferred from the claim text.