# US 9,752,077 B2 · Liquid-crystalline media, components for high-frequency technology, and mesogenic compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,752,077 B2 - Document ID: US9752077B2 - Status: Granted - Kind: B2 - Application number: 13/980,058 - Filed: 2011-12-22 - Published: 2013-11-07 - Granted: 2017-09-05 - Earliest claimed: 2011-01-21 - Assignees: Merck Patent GmbH - Applicants: Atsutaka Manabe; Christian Jasper; Volker Reiffenrath; Elvira Montenegro; Detlef Pauluth; Dagmar Klass - Inventors: Atsutaka Manabe; Christian Jasper; Volker Reiffenrath; Elvira Montenegro; Detlef Pauluth; Dagmar Klass - Web page: https://patentgrep.com/patent/US9752077B2 ## CPC - C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring} - C09K 19/10: containing at least two benzene rings - C09K 19/18: the chain containing carbon-to-carbon triple bonds, e.g. tolans - C09K 19/30: containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings - C09K 19/3059: {in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds} - C09K 19/3098: {Unsaturated non-aromatic rings, e.g. cyclohexene rings} - C09K 2019/183: {Ph-Ph-C≡C-Ph} - C09K 2019/188: {Ph-C≡C-Ph-C≡C-Ph} - C09K 2019/3096: {Cyclobutane rings} - C09K 2219/11: used in the High Frequency technical field - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract The present invention relates to a liquid-crystal medium which comprises a component A which consists of one or more compounds of the formula I in which the parameters have the respective meanings given in the claims or in the text, and to the corresponding, novel mesogenic compounds and to the preparation thereof. The present invention likewise relates to the use of these liquid-crystal media, in particular in components for high-frequency technology, and to components of this type which contain media according to the invention, and to the production and use of these components. The components according to the invention are suitable, in particular, as phase shifters in the microwave and millimeter wave region, for microwave and millimeter wave array antennae and very particularly for so-called tuneable “reflectarrays”. ## Claims ### Claim 1 A compound selected from the group of the compounds of the formulae I-3 and I-4, in which R11 and R12, independently of one another, denote unfluorinated alkyl having 1 to 15 C atoms, unfluorinated alkenyl having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcycloalkenylalkyl, each having up to 15 C atoms, and R13 and R14, independently of one another, denote unfluorinated alkyl or unfluorinated alkoxy, each having 1 to 15 C atoms, unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcycloalkenylalkyl, each having up to 15 C atoms, and alternatively one of R13 and R14 also denotes H. ### Claim 2 (depends on 1) A liquid crystal mixture comprising a compound selected from the group of the compounds of the formulae I-3 and I-4 of claim 1. ### Claim 3 (depends on 2) A liquid-crystal mixture according to claim 2, which comprises one or more compounds of the formula I-3. ### Claim 4 (depends on 2) A liquid-crystal mixture according to claim 2, which comprises one or more compounds of the formula I-4. ### Claim 5 (depends on 2) A liquid-crystal mixture according to claim 2, which further comprises one or more compounds of the formula I-1 or I-2: in which L1 denotes alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms or cycloalkenyl having 4 to 6 C atoms, X1 denotes H, alkyl having 1 to 3 C atoms or halogen, and R11 and R12, independently of one another, denote unfluorinated alkyl having 1 to 15 C atoms, unfluorinated alkenyl having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcycloalkenylalkyl, each having up to 15 C atoms. ### Claim 6 (depends on 2) A liquid-crystal mixture according to claim 2, which additionally comprises one or more components selected from the group of the following components B to E: a strongly dielectrically positive component, component B, which has a dielectric anisotropy of 10 or more, a strongly dielectrically negative component, component C, which has a dielectric anisotropy having a value of 5 or more, a component D which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and consists of compounds having seven or more five- or six-membered rings, and a component E which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and consists of compounds having up to six five- or six-membered rings. ### Claim 7 (depends on 6) A liquid-crystal mixture according to claim 6, which comprises a component B. ### Claim 8 (depends on 6) A liquid-crystal mixture according to claim 6, which comprises a component C. ### Claim 9 (depends on 6) A liquid-crystal mixture according to claim 6, which comprises a component D. ### Claim 10 (depends on 6) A liquid-crystal mixture according to claim 6, which comprises a component E. ### Claim 11 (depends on 2) A liquid-crystal mixture according to claim 2, which further comprises one or more compounds of the formula VI: in which L61 denotes R61 and, in the case where Z61 and/or Z62 denote trans-CH═CH— or trans-CF═CF—, alternatively also denotes X61, L62 denotes R62 and, in the case where Z61 and/or Z62 denote trans-CH═CH— or trans-CF═CF—, alternatively also denotes X62, R61 and R62, independently of one another, denote 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, X61 and X62, independently of one another, denote F or Cl, —CN, —NCS, —SF5, fluorinated alkyl or alkoxy having 1 to 7 C atoms or fluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 7 C atoms, or —NCS, one of Z61 and Z62 denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other, independently thereof, denotes trans-CH═CH—, trans-CF═CF— or a single bond, and to independently of one another, denote ### Claim 12 (depends on 2) A component for high-frequency technology, comprising a liquid-crystal mixture according to claim 2. ### Claim 13 (depends on 12) A microwave antenna array, comprising one or more components according to claim 12. ### Claim 14 (depends on 1) A compound of claim 1, which is a compound of formula I-3. ### Claim 15 (depends on 1) A compound of claim 1, which is a compound of formula I-4.