Classifications

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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
  • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
  • C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
  • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
  • C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
  • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
  • C09K2019/123—Ph-Ph-Ph
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
  • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
  • C09K2019/124—Ph-Ph-Ph-Ph
• • C—CHEMISTRY; METALLURGY
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
  • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
  • C09K2019/183—Ph-Ph-C≡C-Ph
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  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
  • C09K2219/11—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used used in the High Frequency technical field

Definitions

• the present invention relates to liquid-crystalline media and high-frequency components containing these media, in particular microwave components for high-frequency devices, such as devices for phase shifting microwaves, in particular for "microwave phased-array antennas".
• Liquid-crystalline media have long been in electro-optical
• Displays Liquid Crystal Displays - LCDs used to display information.
• Liquid-crystal media in microwave technology inter alia in
• liquid-crystalline media with special, so far rather unusual, unusual properties, or combinations of properties are needed.
• liquid-crystalline media having a suitably high ⁇
• a suitable, nematic a suitable, nematic
• Phase range and ⁇ n can be realized, which do not have the disadvantages of the materials of the prior art, or at least only to a significantly lesser extent.
• liquid-crystalline media comprise - at least one compound of the formula I and
• R 11 and R 12 independently of one another are H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms , preferably alkyl or unfluorinated alkenyl,
• X 11 and X 12 independently of one another are H, F, Cl, -CN, -NCS, -SF 5 , fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl with 2 to 7 carbon atoms, preferably fluorinated alkoxy, fluorinated alkenyloxy, F or Cl, and independently of each other
• R 21 and R 22 independently of one another are H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy, or unfluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, Atoms, preferably alkyl or unfluorinated alkenyl, mean
• X 21 and X 22 independently of one another are F or Cl, -CN 1 -NCS, -SF 5 , fluorinated alkyl or alkoxy having 1 to 7 C atoms or fluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 7 C atoms, or -NCS , preferably -NCS, mean one of
• R 31 and R 32 independently of one another are H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms , preferably alkyl or unfluorinated alkenyl,
• X "and X, 32 independently of one another are H, F, Cl, -CN, -NCS, -SF 5 , fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl with 2 to 7 carbon atoms, preferably fluorinated alkoxy, fluorinated alkenyloxy, F or Cl, and
• the liquid-crystalline media comprise one or more compounds of the formula I and one or more compounds of the formula III.
• the liquid-crystalline media comprise one or more compounds of the formula I and one or more compounds of the formula II.
• liquid-crystalline media according to the present invention comprise one or more compounds of the formula II and one or more compounds of the formula III.
• liquid-crystalline media containing one or more compounds of the formula I, one or more compounds of the formula II and one or more compounds of the formula III.
• the liquid-crystalline media according to the present application contain a total of 15 to 90%, preferably 20 to 85% and particularly preferably 25 to 80%, of compounds of the formula I.
• the liquid-crystalline media preferably contain a total of 1 to 70%, preferably 2 to 65% and particularly preferably 3 to 60%, of compounds of the formula II.
• the liquid-crystalline media according to the present application contain a total of 0 to 60%, preferably 5 to 55% and particularly preferably 10 to 50%, of compounds of the formula III.
• the concentration of the compounds of the formula I is preferably 45 to 75%, preferably 50 to 70% and particularly preferably 55 to 65%, the concentration of the compounds of the formula II preferably 1 to 20%, preferably 2 to 15% and particularly preferably 3 to 10% and the concentration of the compounds of the formula III preferably 1 to 30%, preferably 5 to 25% and especially preferably 5 to 20%.
• the concentration of the compounds of formula I is preferably 15 to 40%, preferably 20 to 35% and particularly preferably 25 to 30%, the concentration of the
• Compounds of the formula III preferably 25 to 50%, preferably 30 to 45% and particularly preferably 35 to 40%.
• liquid-crystalline media in each case one or more compounds of formulas I and II, but not more than 5%, and preferably no
• the concentration of compounds of formula I is preferably 10 to 50%, preferably 20 to 40% and particularly preferably 25 to 35%, the concentration of
• the liquid-crystalline media according to the present application contain a total of 50 to 80%, preferably 55 to 75% and particularly preferably 57 to 70%, of compounds of the formula 1-1 and / or a total of 5 to 70%, preferably 6 to 50% and particularly preferably 8 to 20% of compounds selected from the group of the compounds of the formulas I-2 and I-third
• liquid-crystalline media according to the present application contain a total of 5 to 60%, preferably 10 to 50% and particularly preferably 7 to 20% of compounds of formula II.
• the compounds of formulas I to III each comprise dielectrically positive compounds having a dielectric anisotropy of more than 3, dielectrically neutral compounds having a dielectric anisotropy of less than 3 and more than -1.5, and dielectrically negative compounds having a dielectric anisotropy of -1 , 5 and less.
• the liquid-crystal medium contains one or more compounds of the formula I, preferably selected from the group of the compounds of the formulas 1-1 to I-3, preferably of the formulas 1-1 and / or I-2 and / or I-3, preferably of the formulas I-1 and I-2, more preferably these compounds of the formula I predominantly, even more preferably they consist essentially and very particularly preferably they consist entirely of:
• R 11 unfluorinated alkyl having 1 to 7 carbon atoms or
• R 12 is unfluorinated alkyl having 1 to 7 carbon atoms or
• X 11 and X 12 independently of one another denote F, Cl, -OCF 3 , -CF 3 , -CN, -NCS or -SF 5 , preferably F, Cl, -OCF 3 , or -CN.
• the compounds of the formulas 1-1 are preferably selected from the group of the compounds of the formulas Ma to l-1d, more preferably these compounds of the formula I are predominantly, even more preferably they consist substantially and very particularly preferably they consist entirely of:
• Y 11 and Y 12 are each independently H or F, and preferably
• R 11 is alkyl or alkenyl
• the compounds of the formula I-2 are preferably selected from the group of the compounds of the formulas I-2a to I-2e and / or from the group of the compounds of the formulas I-2f and I-2g, more preferably these compounds of the formula I are present They are essentially, even more preferably essentially, and most preferably they consist entirely of:
• Y 11 and Y 12 are each independently H or F, and preferably
• 11 is F 1 Cl or -OCF 3 , and preferably one of
• the compounds of the formula 1-3 are preferably compounds of the formula I-3a: wherein the parameters have the respective meanings given above for formula 1-1 and in which preferred
• X 11 F, Cl 1 is preferably F
• X 12 F 1 Cl or -OCF 3 preferably -OCF 3 means.
• the compounds of the formula I are selected from the group of the compounds I-1a to I-1d, preferably selected from the group of the compounds I-1 C and I-1 D, more preferably the
• Compounds of the formula I are predominantly, even more preferably substantially, and are very particularly preferably composed completely of them.
• the compounds of the formula I-1a are preferably selected from the group of the compounds of the formulas I-1a-1 and I-1a. 2, more preferably, these compounds of formula 1-1 a predominantly, even more preferably they consist essentially and very particularly preferably they consist entirely of:
• R 11 has the meaning given above and preferred
• C n H 2n + I means in which n is an integer in the range from 0 to 7, preferably in the range from 1 to 5 and more preferably 3 or 7.
• the compounds of the formula 1-1 b are preferably compounds of the formula 1-1 b-1: wherein
• R 11 has the meaning given above and preferred
• n is an integer in the range of 0 to 15, preferably in
• the compounds of the formula 1-1 c are preferably selected from the group of the compounds of the formulas 1-1 c-1 and 1-1 c-4, preferably selected from the group of the compounds of the formulas I-1c-1 and 1-1 c-2, more preferably, these compounds of formula 1-1 c predominantly, even more preferably they consist essentially and very particularly preferably they consist entirely of:
• R 11 has the meaning given above and preferred
• n is an integer in the range of 0 to 15, preferably in
• the compounds of the formula I-1 d are preferably selected from the group of the compounds of the formulas I-1d-1 and I-1d-2, preferably the compound of the formula I-1-d-2, more preferably these are
• C n H 2n + i means in which an integer in the range of 0 to 15, preferably in the range of 1 to 7 and more preferably 1 to 5 means.
• the compounds of the formula I-2a are preferably selected from the group of the compounds of the formulas I-2a-1 and I-2a-2, preferably of the compounds of the formulas I-1a-1, more preferably these compounds of the formula I 2a predominantly, even more preferably they consist essentially and very particularly preferably they consist entirely of:
• n and m are independently an integer in the range of 0 to 15, preferably in the range of 1 to 7, and more preferably 1 to 5 and z is 0, 1, 2, 3 or 4, preferably 0 or 2.
• Preferred compounds of the formula I-2b are the compounds of the formula I-2b-1: wherein
• R 11 and R 12 The preferred combination of (R 11 and R 12 ) is here in particular (C n H 2n + I and C m H 2m + i).
• Preferred compounds of the formula I-2c are the compounds of the formula I-2c-1: wherein
• R 11 has the meaning given above and preferred
• Preferred compounds of the formula I-2d are the compounds of the formula I-2d-1: wherein
• R 11 has the meaning given above and preferred
• R 12 has the meaning given above and preferred
• Preferred compounds of the formula I-2e are the compounds of the formula I-2e-1: wherein
• the preferred combination of (R 11 and R 12 ) is here in particular (C n H 2n + I and OC m H 2m + i).
• Preferred compounds of the formula I-2f are the compounds of the formula I-2f 1: wherein
• R 11 has the meaning given above and preferred
• Preferred compounds of the formula I-2g are the compounds of the formula I-2g-1: wherein
• n11 has the meaning given above and preferred
• R 12 has the meaning given above and preferred
• (R 11 and R 12 ) are here in particular (C n H 2n + I and C m H 2m + 1 ) and (C n H 2n + I and OC m H 2m + i), particularly preferably (C n H 2n + 1 and OC m H 2m + 1 ).
• the compounds of the formulas II are preferably selected from the group of the compounds of the formulas 11-1 to II-4, more preferably these compounds of the formula II are predominantly, even more preferably they consist substantially and very particularly preferably they consist entirely of:
• R 21 and R 22 are independently H, unfluorinated alkyl or
• R 22 is C m H 2m + i or OC m is H 2m + i or (CH 2 )
• the compounds of the formula 11-1 are preferably selected from the group of the compounds of the formulas 11-1a and 11-1b, preferably selected from the group of the compounds of the formula 11-1a, more preferably these compounds of the formula 11- 1 predominantly, even more preferably they consist essentially and very particularly preferably they consist entirely of:
• R 21 has the meaning given above and preferred
• R 22 has the meaning given above and preferred
• the preferred combinations of (R 21 and R 22 ) are especially (C n H 2n + I and C m H 2m + 1 ) and (C n H 2n + I and OC m H 2m + i), in formula 11-1 a particularly preferably (C n H 2n + I and C m H 2m + i) and formula 11-1 b
• the compounds of the formula II-2 are preferably compounds of the formula II-2a: wherein
• R 21 has the meaning given above and preferred
• R 22 has the meaning given above and preferred
• n and m are independently an integer in the range of 0 to 15, preferably in the range of 1 to 7 and particularly preferably 1 to 5 and z is 0, 1, 2, 3 or 4, preferably 0 or 2.
• the compounds of the formula II-3 are preferably compounds of the formula II-3a:
• n is an integer in the range of 0 to 7, preferably in
• the compounds of the formula II-4 are preferably compounds of the formula II-4a:
• R 21 has the meaning given above and preferred
• n is an integer in the range of 0 to 7, preferably in
• n is an integer in the range of 0 to 7, preferably in
• Range from 1 to 5 means.
• the compounds of the formula III are preferably selected from the group of the compounds of the formulas III-III through III-7, more preferably these compounds of the formula III are predominantly, even more preferably they consist essentially and very particularly preferably consist entirely of them.
• R 31 denotes unfluorinated alkyl or alkoxy each having 1 to 7 C atoms or unfluorinated alkenyl having 2 to 7 C atoms,
• R 32 is unfluorinated alkyl or alkoxy, each having 1 to 7 carbon atoms or unfluorinated alkenyl having 2 to 7 carbon atoms, and
• X is 32 F, Cl, or -OCF 3 , preferably F, and
• z is 0, 1, 2, 3 or 4, preferably 0 or 2.
• the compounds of the formula III-1 are preferably selected from the group of the compounds of the formulas III-Ia to Hl-Id, more preferably these compounds of the formula III-1 predominantly, even more preferably they consist essentially and very particularly preferably they consist completely from it:
• X, 32 has the meaning given above in formula III-2 and , 31 has the abovementioned meaning and preferably C n H 2n + i, where n is 1 to 7, preferably 2 to 6, particularly preferably 2, 3 or 5 and
• X 32 is preferably F.
• the compounds of the formula III-2 are preferably selected from the group of the compounds of the formulas III-2a and III-2b, preferably of the formula III-2a, more preferably these compounds of the formula III-2 predominantly, even more preferably they consist in Essentially, and most preferably, they consist entirely of:
• R 31 has the meaning given above and preferred
• R 32 has the meaning given above and preferred
• the preferred combinations of (R 31 and R 32 ) are here in particular (C n H 2n + I and C m H 2m + 1 ) and (C n H 2n + I and OC m H 2m + 1 ), particularly preferably (C n H 2n + I and C m H 2m + i).
• the compounds of the formula III-3 are preferably compounds of the formula III-3a:
• R 31 has the meaning given above and preferred
• R 32 has the meaning given above and preferred
• the preferred combinations of (R 31 and R 32 ) are here in particular (C n H 2n + I and C m H 2m + i) and (C n H 2n + 1 and OC m H 2m + 1 ), particularly preferably (C n H 2n + 1 and C m H 2m + 1 ).
• the compounds of the formula III-4 are preferably compounds of the formula III-4a: a wherein
• R 32 has the meaning given above and preferred
• n and m are independently an integer in the range of 0 to 15, preferably in the range of 1 to 7 and especially preferably 1 to 5 and z is 0, 1, 2, 3 or 4, preferably 0 or 2.
• the compounds of the formula III-5 are preferably selected from the group of the compounds of the formulas III-5a and III-5b, preferably of the formula III-5a, more preferably these compounds of the formula III-5 predominantly, even more preferably essentially and most preferably, they consist entirely of:
• R 31 has the meaning given above and preferred
• R 32 has the meaning given above and preferred
• n and m independently of one another denote an integer in the range from 0 to 15, preferably in the range from 1 to 7 and particularly preferably 1 to 5, and
• z is 0, 1, 2, 3 or 4, preferably 0 or 2.
• the preferred combinations of (R 31 and R 32 ) are here in particular (C n H 2n + - I and C m H 2m + 1 ) and (C n H 2n + 1 and OC m H 2m + i), particularly preferably (C n H 2n + I and C m H 2m + i).
• the compounds of the formula III-6 are preferably selected from the group of the compounds of the formulas III-6a and III-6b, more preferably these compounds of the formula III-6 predominantly, even more preferably they consist essentially and very particularly preferably they consist completely from it:
• R 31 has the meaning given above and preferred
• the preferred combinations of (R 31 and R 32 ) are here in particular (C n H 2n + 1 and C m H 2m + i) and (C n H 2n + 1 and OC m H 2m + 1 ), particularly preferably (C n H 2n + 1 and C m H 2m + 1 ).
• the media according to the present invention contain one or more compounds of formula IV wherein
• R 41 and R 42 independently of one another are H, unfluorinated alkyl or
• the liquid-crystalline media according to the present application contain a total of 0 to 40%, preferably 0 to 30% and particularly preferably 5 to 25% of compounds of formula IV.
• the compounds of the formula IV are preferably selected from the group of the compounds of the formulas IV-1 to IV-3, more preferably these compounds of the formula IV are predominantly, even more preferably they consist substantially and very particularly preferably they consist entirely of: wherein
• Y 41 and Y 42 signify H and the other signifies H or F
• R 41 has the meaning given above and preferred
• R 42 has the meaning given above and preferred
• the preferred combinations of (R 41 and R 42 ) are particularly preferred here (C n H 2n + I and C m H 2m + i) and (C n H 2n + I and O-C m H 2 m + i) (C n H 2n + ! And C m H 2rn + i).
• the compounds of formula IV-1 are selected from the group of compounds of formulas IV-Ia to IV-Ic, more preferably these compounds of formula IV-1 are predominantly, even more preferably they are substantially and most preferably they are completely from it: wherein
• R, 41 has the meaning given above and preferred
• R, 42 has the meaning given above and is preferred
• n and m independently of one another an integer in the range of 0 to 15, preferably in the range of 1 to 7 and particularly preferably 1 to 5 and z is 0, 1, 2, 3 or 4, preferably 0 or 2.
• the compounds of the formula IV-2 are preferably compounds of the formula IV-2a:
• R 41 has the meaning given above and preferred
• R 42 has the abovementioned meaning and preferably
• z is 0, 1, 2, 3 or 4, preferably 0 or 2.
• the compounds of the formula IV-3 are preferably compounds of the formula IV-3a:
• R 41 has the meaning given above and preferred
• R 42 has the meaning given above and preferred
• R 41 and R 42 are here in particular (C n H 2n + I and C m H 2m + 1 ) and (C n H 2n + I and OC m H 2m + 1 ).
• the media according to the present invention contain one or more compounds of the formula V wherein
• R 51 and R 52 are each independently H, unfluorinated alkyl or
• X 51 and X 52 independently of one another are H, F, Cl, -CN, -NCS, -SF 5 , fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or alkenyloxy, or unfluorinated or alkoxyalkyl having 2 to 7 C atoms, preferably fluorinated alkoxy, fluorinated alkenyloxy, F or Cl, and
• the compounds of the formula V are preferably selected from the group of the compounds of the formulas V-1 to IV-3, more preferably these compounds of the formula V are predominantly, even more preferably they consist essentially and very particularly preferably consist entirely of:
• R 51 has the meaning given above and preferred
• R 52 has the meaning given above and preferred
• n and m are independently an integer in the range of 0 to 15, preferably in the range of 1 to 7 and particularly preferably 1 to 5 and
• the preferred combinations of (R 51 and R 52 ) are here in particular (C n H 2n + I and C m H 2m + 1 ) and (C n H 2n + I and OC m H 2m + 1 ).
• the liquid-crystalline media according to the present application contain a total of 5 to 30%, preferably 10 to 25% and particularly preferably 15 to 20% of compounds of the formula V.
• the compounds of formula V-1 are selected from the group of compounds of formulas V-1a to V-1e, more preferably these compounds of formula V-1 are predominantly, even more preferably they are substantially and most preferably they are completely from it:
• R 51 has the meaning given above and preferred
• C n H 2n + I means, and an integer in the range of 0 to 15, preferably in the range of 1 to 7 and particularly preferably 1 to 5, and
• X 52 is preferably F or Cl.
• the compounds of formula V-2 are selected from the group of compounds of formulas V-2a and V-2b, more preferably these compounds of formula V-2 are predominantly, even more preferably they are substantially and most preferably they are completely from it:
• R 51 has the meaning given above and preferred
• R 52 has the meaning given above and preferred
• n and m are independently an integer in the range of 0 to 15, preferably in the range of 1 to 7 and particularly preferably 1 to 5 and
• the preferred combination of (R 51 and R 52 ) is here in particular (C n H 2n + i and C m H 2m + i).
• the compounds of the formula V-3 are preferably compounds of the formulas V-3a and V-3b:
• R 51 has the meaning given above and preferred
• R 52 has the meaning given above and preferred
• n and m are independently an integer in the range of 0 to 15, preferably in the range of 1 to 7 and especially preferably 1 to 5 and
• the preferred combinations of (R 51 and R 52 ) are here in particular (C n H 2n + I and C m H 2m + i) and (C n H 2n + I and OC m H 2m + i), particularly preferably (C n H 2n +1 and OC m H 2m + 1 ).
• the medium contains one or more dielectrically positive compounds having a dielectric anisotropy greater than 3 of Formula 1-1.
• the medium contains one or more dielectrically neutral compounds having a dielectric anisotropy in the range greater than -1.5 to 3 of formula I-2.
• the medium contains one or more compounds of the formula II.
• the medium contains one or more compounds of the formula III.
• the liquid-crystalline media according to the present invention contain 10% or less, preferably 5% or less, more preferably 2% or less, most preferably 1% or less, and especially no compound having only two or less five and / or six-membered rings.
• liquid-crystalline media according to the present invention contain compounds selected from the group of
• the entity of interest ie, the medium or component
• the entity of interest contains the indicated component or components or compound or compounds, preferably at a total concentration of 10% or greater, and more preferably 20% or greater
• Predominantly in this context means that the entity in question is 55% or more, preferably 60% or more and most preferably 70% or more of the specified component or components or compound or compounds.
• Substantially in this context means that the entity in question contains 80% or more, preferably 90% or more, and most preferably 95% or more of the indicated component or components or compound or compounds.
• the entity in question contains 98% or more, preferably 99% or more and most preferably 100.0% of the indicated component or components or compound or compounds.
• liquid crystal media preferably a clearing point of 9O 0 C or more, more preferably 100 ° C or more, still more preferably of 120 ° C or more, more preferably 150 ° C or more, and most preferably from 170 ° C or more, up.
• the nematic phase of the media of the invention extends at least from 20 ° C or less to 90 ° C or more, preferably to 100 ° C or more, more preferably at least from 0 ° C or less to 120 ° C or more, most preferably at least from -10 0 C or less to 140 0 C or more and preferably at least from - 20 ° C or less to 150 ° C or more.
• the ⁇ of the liquid crystal medium according to the invention at 1 kHz and 20 0 C is preferably 1 or more, more preferably 2 or more and most preferably 3 or more.
• the .DELTA.n of the liquid crystal media according to the present invention at 589 nm (Na D) and 20 0 C, preferably in the range of 0.200 or more to 0.90 or less, more preferably in the range of 0.250 or more to 0.90 or less, even more preferably in the range of 0.300 or more to 0.85 or less and most preferably in the range of 0.350 or more to 0.800 or less.
• the ⁇ n of the liquid crystal media according to the present invention is preferably 0.50 or more, more preferably 0.55 or more.
• the individual compounds of formula I are preferably used in a total concentration of from 10% to 70%, more preferably from 20% to 60%, even more preferably from 30% to 50% and most preferably from 25% to 45% of
• the compounds of formula II are preferably in a
• Total concentration of from 1% to 20%, more preferably from 1% to 15%, even more preferably from 2% to 15% and most preferably from 3% to 10% of the total mixture.
• the compounds of formula IM are preferably in a
• Total concentration from 1% to 60%, more preferably from 5% to
• the liquid crystal media preferably contain a total of 50% to 100%, more preferably 70% to 100%, and most preferably 80% to
• dielectrically positive describes compounds or components with ⁇ > 3.0, dielectrically neutral with -1.5 ⁇ ⁇ 3.0 and dielectrically negative with ⁇ ⁇ -1.5.
• ⁇ is determined at a frequency of 1 kHz and 20 0 C.
• the dielectric anisotropy of each compound becomes apparent from the results of a 10% solution of each individual compound in a nematic host mixture certainly. If the solubility of each compound in the host mixture is less than 10%, the concentration is reduced to 5%.
• the capacities of the test mixtures are determined in a cell with homeotropic as well as homogeneous orientation.
• the layer thickness is about 20 ⁇ m for both cell types.
• the applied voltage is a square wave with a frequency of 1 kHz and an effective value of typically 0.5V to 1.0V, but is always chosen to be below the capacitive threshold for the particular test mixture.
• ⁇ is defined as ( ⁇ ⁇ - ⁇ x) defined as ⁇ r c D h sc hn. ⁇ ⁇ ⁇ + 2 ⁇ ⁇ ) / 3.
• threshold voltage refers to in the present
• the optical threshold is reported for 10% relative contrast (Vi 0 ), the term saturation voltage refers to the optical saturation and is given for 90% relative contrast (V 90 ), in both cases, unless expressly stated otherwise.
• the capacitive threshold voltage (V 0 ), also called the Freedericks threshold V Fr is only used if expressly stated
• the optical anisotropy ( ⁇ n) is determined at a wavelength of 589.3 nm.
• the dielectric anisotropy ( ⁇ ) is determined at a frequency of 1 kHz.
• the threshold voltages as well as all other electro-optical properties are determined with test cells manufactured at Merck KGaA, Germany. The test cells for the determination of ⁇ have a layer thickness of approximately 20 ⁇ m.
• the electrode is a circular ITO
• the alignment layers are SE-1211 from Nissan Chemicals, Japan, for homeotropic alignment ( ⁇ n) and polyimide AL-1054 from Japan Synthetic Rubber, Japan, for homogeneous alignment ( ⁇ i).
• Capacitance is determined using a Solatron 1260 frequency response analyzer using a sine wave with a voltage of 0.3 V rms .
• the light used in the electro-optical measurements is white light. In this case, a structure with a commercially available device DMS Fa. Autronic Melchers, Germany is used. The characteristic stresses were determined under vertical observation.
• the alignment layers are SE-1211 from Nissan Chemicals, Japan, for homeotropic alignment ( ⁇ n) and polyimide AL-1054 from Japan Synthetic Rubber, Japan, for homogeneous alignment ( ⁇ i).
• Capacitance is determined using a Solatron 1260 frequency response analyzer using a sine wave with a voltage of 0.3 V rms .
• Threshold voltage (V 10 ), mid-gray voltage (V 50 ) and saturation voltage (V 90 ) were determined for 10%, 50% and 90% relative contrast, respectively.
• the liquid-crystalline media are examined for their properties in the microwave frequency range as in A. Penirschke, S. Müller, P. Scheele, C. Weil, M. Wittek, C. Hock and R. Jakoby: "Cavity Perturbation Method for Characterization of Liquid Crystals up to 35GHz ",
• the liquid crystal is filled in a capillary made of polytetrafluoroethylene (PTFE).
• the capillary has an inner radius of 180 ⁇ m and an outer radius of 350 ⁇ m.
• the effective length is 2.0 cm.
• the filled capillary is placed in the center of the cavity at a resonant frequency of 30 GHz. This cavity has a length of 6.6 mm, a width of 7.1 mm and a height of 3.6 mm. Then that will
• the dielectric constant and the loss angle at the corresponding target frequency are calculated by the equations 10 and 11 of FIG A. Penirschke, S.
• the values for the components of the properties perpendicular or parallel to the director of the liquid crystal are determined by orientation of the liquid crystal
• Liquid crystal in a magnetic field For this purpose, the magnetic field of a permanent magnet is used. The strength of the magnetic field is 0.35 Tesla. The orientation of the magnet is adjusted accordingly and then rotated accordingly by 90 °.
• Preferred devices are phase shifters, varactors, radio and radio wave antenna arrays, matching circuit adaptive filters, etc. In the present application, unless expressly stated otherwise, the term compounds means both one compound and several compounds.
• liquid-crystal media according to the invention are preferred.
• nematic phases each of at least from -20 0 C to 80 0 C, preferably from -30 ° C to 85 ° C and most preferably from -40 0 C to 100 0 C on. Particularly preferably the phase extends to 120 0 C or more, preferably to 140 ° C or more, and most preferably up to 180 0 C or more.
• the term "nematic phase” means, on the one hand, that no smectic phase and no crystallization are observed at low temperatures at the corresponding temperature, and, on the other hand, that no clarification occurs on heating from the nematic phase.
• the investigation at low temperatures is carried out in a flow viscometer at the appropriate temperature and checked by storage in test cells, with a layer thickness of 5 microns, for at least 100 hours. At high temperatures, the clearing point is measured in capillaries by conventional methods.
• liquid-crystal media according to the invention are characterized by high optical anisotropies in the visible range.
• Birefringence at 589 nm is preferably 0.20 or more, more preferably 0.25 or more, more preferably 0.30 or more, even more preferably 0.40 or more, and most preferably 0.45 or more.
• the birefringence is preferably 0.80 or less.
• the liquid crystals used have a positive
• the liquid-crystal media according to the invention are characterized by high anisotropies in the microwave range.
• the birefringence is for example at about 8.3 GHz preferably 0.14 or more, more preferably 0.15 or more, more preferably 0.20 or more, more preferably 0.25 or more and most preferably 0.30 or more , In addition, the birefringence is preferably 0.80 or less.
• Liquid crystal materials is 5 or more, preferably 6 or more, preferably 8 or more, preferably 10 or more, preferably 15 or more, preferably 17 or more, more preferably 20 or more and most preferably 25 or more.
• the preferred liquid crystal materials have phase shift ratings of 157 dB or more, preferably 207 dB or more, preferably 307 dB or more, preferably 407 dB or more, preferably 507 dB or more, more preferably 807 dB or more, and most preferably 1007 dB or more.
• liquid crystals having a negative value of dielectric anisotropy may also be used to advantage.
• the liquid crystals used are either individual substances or mixtures. Preferably, they have a nematic phase.
• alkyl preferably includes straight-chain and branched alkyl groups having 1 to 15 carbon atoms, in particular the
• alkenyl preferably comprises straight-chain and branched alkenyl groups having 2 to 15 carbon atoms, in particular the straight-chain groups.
• Particularly preferred alkenyl groups are C 2 to C 7 -I E-alkenyl, C 4 to C 7 -3E-alkenyl, C 5 to C 7 -4-alkenyl, C 6 to C 7 -5-alkenyl and C 7 -6-alkenyl, in particular C 2 to C 7 -I E-alkenyl, C 4 to C 7 - 3E-alkenyl and C 5 to C 7 -4 alkenyl.
• alkenyl groups are vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl,
• fluoroalkyl preferably includes straight-chain fluoro-end-capped groups, ie, fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, and 7-fluoroheptyl, but other positions of the fluorine are not excluded ,
• oxaalkyl or alkoxyalkyl preferably comprises straight-chain radicals of the formula C n H 2n + iO- (CH 2 ) m , in which n and m are each independently of one another 10.
• n is 1 and m is 1 to 6.
• Vinyl-terminated compounds and compounds having a methyl end group have low rotational viscosity.
• both high-frequency and ultra-high frequency techniques mean applications with frequencies in the range of 1 MHz to 1 THz, preferably from 1 GHz to 500 GHz, more preferably 2 GHz to 300 GHz, most preferably from about 5 to 150 GHz.
• the liquid crystal media according to the present invention may include further additives and chiral dopants in the usual concentrations.
• the total concentration of these other ingredients is in the range of 0% to 10%, preferably 0.1% to 6%, based on the total mixture.
• the concentrations of the individual compounds used are preferably each in the range of 0.1% to 3%.
• the concentration of these and similar additives is not taken into account in the specification of the values and concentration ranges of the liquid crystal components and liquid crystal compounds of the liquid crystal media in this application.
• the liquid-crystal media according to the invention consist of several compounds, preferably from 3 to 30, more preferably from 4 to 20 and most preferably from 4 to 16 compounds. These compounds are mixed in a conventional manner. In general, the desired
• Amount of the compound used in the smaller amount dissolved in the compound used in the larger amount If the temperature is above the clearing point of the compound used in the higher concentration, the completion of the dissolution process is particularly easy to observe.
• premixes which may be e.g. may be homologous or eutectic mixtures of compounds, or using so-called "multi-bottle" systems, the ingredients of which are themselves ready-to-use mixtures.
• V-CH CH-Zl -0-C0-
• the exemplary structures are particularly preferably used compounds having three 6-membered rings:
• the exemplary structures are particularly preferably used compounds having four 6-membered rings:
• the total concentration of these or similar compounds in the media is preferably 5% or less.
• the mesogenic media contain one or more compounds selected from the group of compounds of Table E.
• Table F 1 example compounds are compiled, which can be used in the mesogenic media according to the present invention preferably as chiral dopants.
• the mesogenic media contain one or more compounds selected from the group of compounds of Table F.
• the mesogenic media according to the present application contain two or more, preferably four or more, compounds selected from the group consisting of the compounds of the above tables.
• the liquid crystal media according to the present invention preferably contain
• a liquid crystal mixture M-1 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal composition M-2 having the composition and properties as shown in the following table is prepared.
• a liquid crystal mixture M-3 having the composition and properties as shown in the following table is prepared.
• a liquid crystal composition M-4 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-5 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-6 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-7 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-8 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-9 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-10 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-11 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-12 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-13 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a liquid crystal mixture M-14 having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a M-15 liquid crystal composition having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a M-16 liquid crystal composition having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.
• a M-17 liquid crystal composition having the composition and properties as shown in the following table is prepared.
• Microwave range especially for phase shifters.

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• 2009
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