Aromatic isothiocyanates

Abstract

Aromatic isothiocyanates are provided. The present invention relates to aromatic isothiocyanates of formula U as defined in claim 1, to liquid crystalline media comprising one or more compounds of formula U, and to high frequency components, in particular microwave components for high frequency devices, comprising these media, such as devices for shifting the phase of microwaves, tunable filters, tunable material structures and electron beam steering antennas, e.g. phased array antennas. TIFF2022545908000302.tif54166

Description

[Technical Field]

[0001] The present invention relates to aromatic isothiocyanates, liquid crystalline media containing them, high frequency components containing these media, in particular microwave components for high frequency devices, such as devices for shifting the phase of microwaves, tunable filters, tunable material structures and electron beam steering antennas (e.g. phased array antennas), and devices containing said components. [Background technology]

[0002] Liquid crystalline media have been used for many years in electro-optical displays (liquid crystal displays: LCDs) for displaying information. However, in recent years, the use of liquid crystalline media in components for microwave technology has also been proposed, for example in German Patent Application No. 10 2004 029 429.1 and JP 2005-120208 A1.

[0003] A. Gaebler, F. Goelden, S. Muller, A. Penirschke and R. Jakoby, "Direct Simulation of Material Permittivites using an Eigen-Susceptibility Formulation of the Vector Variational Approach", 12MTC 2009 - International Instrumentation and Measurement Technology Conference, Singapore, 2009 (IEEE), pp. 463-467 (Non-Patent Document 1), describes the corresponding properties of the known liquid crystal mixture E7 (Merck, Germany).

[0004] German Patent Application No. 10 2004 029 429.1 (Patent Document 1) describes the use of liquid crystal media in microwave technology, especially in phase shifters. There, liquid crystal media are discussed with respect to their properties in the corresponding frequency range, and liquid crystal media based mainly on mixtures of aromatic nitriles and isothiocyanates are presented.

[0005] Fluorine atoms are commonly used in mesogenic compounds to introduce polarity, and high dielectric anisotropy values ​​can be achieved, especially in combination with terminal NCS groups.

[0006] WO 2014 / 116238 proposes perfluorinated biphenylyl isothiocyanate for use in chemical sensing devices, without any discussion of mesogenic properties.

[0007] DE-A 2 982 730 describes mixtures which consist entirely of isothiocyanate compounds.

[0008] However, the compositions available for use in microwave applications still have some drawbacks. There is a need to improve these media with regard to their general physical properties, storage stability, and stability under operation in devices. In view of the large number of different parameters that must be considered and improved for the development of liquid crystalline media for microwave applications, it is desirable to have a wider range of possible mixture components for the development of such liquid crystalline media. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] German Patent Application No. 10 2004 029 429.1 [Patent Document 2] Japanese Patent Application Laid-Open No. 2005-120208 [Patent Document 3] International Publication No. 2014 / 116238 [Patent Document 4] DE 2 982 730 A1 [Non-patent literature]

[0010] [Non-Patent Document 1] A. Gaebler, F. Goelden, S. Muller, A. Penirschke and R. Jakoby, "Direct Simulation of Material Permittivites using an Eigen-Susceptibility Formulation of the Vector Variational Approach," 12MTC 2009 - International Instrumentation and Measurement Technology Conference, Singapore, 2009 (IEEE), pp. 463-467. Summary of the Invention [Problem to be solved by the invention]

[0011] It is an object of the present invention to provide compounds for use in liquid-crystalline media which have improved properties relevant for application in the microwave range of the electromagnetic spectrum. [Means for solving the problem]

[0012] To solve the problem, compounds of formula U shown below and liquid crystal media comprising compounds are provided. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present invention relates to compounds of formula U:

[0014] [ka]

[0015] During the ceremony, R U represents 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 are [ka] or the group R P represents R P is halogen, CN, NCS, R F , R F -O- or R F -S-, where R F represents a fluorinated alkyl or alkenyl having up to 9 C atoms, Z U1 , Z U2 are the same or different and represent -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C- or a single bond, preferably -C≡C- or a single bond; X 1 , X 2 , X 3 and X 4 are the same or different and represent Cl or F, preferably F; t is 0 or 1, and [ka] represents a group selected from the following groups: a) the group consisting of 1,4-phenylene, 1,4-naphthylene and 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, with the exception of tetrafluoro-1,4-phenylene; 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 CH groups may be replaced by -O- and / or -S-, and in which one or more H atoms may be replaced by F; 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, in each occurrence, is the same or different and represents F, Cl, CN, SCN, SF5, or a linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy having 1 to 12 C atoms, which may in each case be fluorinated.

[0016] The present invention further relates to compounds of formula UN.

[0017] [ka]

[0018] During the ceremony, R U represents alkyl or alkoxy having 1 to 12 C atoms or alkenyl, alkenyloxy or alkoxyalkyl having 3 to 12 C atoms, in which one or more CH2 groups are [ka] or the group R P where R P is halogen, CN, NCS, R F , R F -O- or R F -S-, where R Frepresents a fluorinated alkyl or alkenyl having up to 9 C atoms, In said group the other groups and parameters have the meanings given above for formula U, Rather, compounds [ka] is excluded, In the formula, R U , X 1 , X 2 , X 3 and X 4 has the meaning given above for formula U.

[0019] According to another aspect of the present invention, there is provided a method for synthesizing a compound of formula U from a compound of formula UN.

[0020] The invention further relates to liquid-crystalline media comprising compounds of the formula U and to the use of liquid-crystalline media comprising compounds of the formula U in components for high-frequency technology.

[0021] According to another aspect of the present invention there are provided components and devices including said components, all of which are operable in the microwave range of the electromagnetic spectrum. Preferred components are phase shifters, varactors, radio and radio frequency antenna arrays, matching circuits and adaptive filters.

[0022] Preferred embodiments of the invention are the subject matter of the independent claims or can be seen from this description.

[0023] It has surprisingly been found that by using compounds of formula U in liquid-crystalline media it is possible to achieve liquid-crystalline media which have high dielectric anisotropy, suitably fast switching times, a suitable nematic phase range, high tunability and low dielectric losses, while at the same time having excellent stability.

[0024] The media according to the invention are distinguished by a high clearing temperature, a wide nematic phase range and excellent low-temperature stability (LTS), so that devices containing the media can operate under extreme temperature conditions.

[0025] The medium is further distinguished by a high value of the dielectric anisotropy and a low rotational viscosity. As a result, the threshold voltage, i.e., the minimum voltage at which the device can switch, is very low. A low operating voltage and a low threshold voltage are desirable to achieve devices with improved switching characteristics and high energy efficiency. A low rotational viscosity allows the device according to the invention to switch quickly.

[0026] In particular, the media according to the present invention exhibit improved (ie lower) dielectric loss.

[0027] These properties make the medium as a whole particularly suitable for use in components and devices for applications in radio frequency technology and the microwave range, in particular devices for shifting the phase of microwaves, tunable filters, tunable material structures and electronic beam steering antennas (e.g. phased array antennas).

[0028] In this specification, "high frequency technology" refers to the use of electromagnetic waves having frequencies in the range of 1 MHz to 1 THz, preferably 1 GHz to 500 GHz, more preferably 2 GHz to 300 GHz, and particularly preferably about 5 GHz to 150 GHz.

[0029] In the present specification, halogen is F, Cl, Br or I, preferably F or Cl, particularly preferably F.

[0030] In this specification, alkyl is linear or branched and has 1 to 15 C atoms, preferably linear and, unless otherwise indicated, has 1, 2, 3, 4, 5, 6 or 7 C atoms, and is therefore preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0031] In this specification, branched alkyl is preferably isopropyl, sec-butyl, isobutyl, isopentyl, 2-methylhexyl or 2-ethylhexyl.

[0032] In this specification, an alkoxy group is linear or branched and contains 1 to 15 C atoms, which is preferably linear and, unless otherwise stated, has 1, 2, 3, 4, 5, 6 or 7 C atoms, and is therefore preferably methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy or n-heptoxy.

[0033] In this specification, the alkenyl group is preferably an alkenyl group having 2 to 15 carbon atoms, which is linear or branched and contains at least one C-C double bond. It is preferably linear and has 2 to 7 carbon atoms. Thus, it is preferably vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, or hept-1-, -2-, -3-, -4-, -5- or -6-enyl. If two carbon atoms of the C-C double bond are substituted, the alkenyl group may be in the form of an E and / or Z isomer (trans / cis). Generally, the respective E isomers are preferred. Of the alkenyl groups, prop-2-enyl, but-2- and -3-enyl and pent-3- and -4-enyl are particularly preferred.

[0034] In the present specification, alkynyl is understood to mean an alkynyl group having 2 to 15 C atoms, which is linear or branched and contains at least one C-C triple bond. 1- and 2-propynyl and 1-, 2- and 3-butynyl are preferred.

[0035] R F represents a halogenated alkyl, alkoxy, alkenyl or alkenyloxy, it may be branched or unbranched. Preferably, it is unbranched and monofluorinated, polyfluorinated or perfluorinated, preferably perfluorinated, and has 1, 2, 3, 4, 5, 6 or 7 C atoms, and in the case of alkenyl, 2, 3, 4, 5, 6 or 7 C atoms.

[0036] R P is preferably CN, NCS, Cl, F, -(CH2) n -CH=CF2, -(CH2) n -CH=CHF, -(CH2) n -CH=Cl2, -C n F 2n+1 , -(CF2) n -CF2H, -(CH2) n -CF3, -(CH2) n -CHF2, -(CH2) n CH2F, -CH=CF2, -O(CH2) n -CH=CF2, -O(CH2) n CHCl2, -OC n F 2n+1 , -O(CF2) n -CF2H, -O(CH2) n CF3, -O(CH2) n -CHF2, -O(CF) n CH2F, -OCF=CF2, -SC n F 2n+1 , -S(CF) n -CF3, where n is an integer of 0 to 7.

[0037] Compounds of general formula U can be prepared in a manner known per se, as described in the literature (for example in standard works such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), under the precise reaction conditions appropriate for said reaction, whereby modifications known per se, but not mentioned in more detail here, can be used.

[0038] If desired, the starting material can also be formed in situ by not isolating it from the reaction mixture but immediately converting it further into a compound of general formula U.

[0039] Preferred synthetic routes to compounds of the present invention are illustrated in the schemes below and further explained by the examples. Suitable syntheses are also published, for example, in Juanli Li, Jian Li, Minggang Hu, Zhaoyi Che, Lingchao Mo, Xiaozhe Yang, Zhongwei An and Lu Zhang (2017) The effect of locations of triple bond at terphenyl skeleton on the properties of isothiocyanate liquid crystals, Liquid Crystals, Vol. 44: No. 9, pp. 1374-1383, and can be tailored to specific desired compounds of general formula U by selection of appropriate starting materials.

[0040] A preferred intermediate is 4-bromo-2,3,5,6-tetrafluoroaniline, which can be reacted to give compounds of general formula UN, for example, by cross-coupling reactions commonly known as Suzuki, Stille, Sonogashira reactions, etc. A preferred route is illustrated in Scheme 1, where the groups and parameters have the meanings defined in claim 1.

[0041] [ka]

[0042] [ka]

[0043] Preferred reagents for the process according to the invention for converting compounds of formula UN into compounds of formula U (Scheme 3) are carbon disulfide, thiophosgene, thiocarbonyldiimidazole, di-2-pyridylthiocarbonate, bis(dimethylthiocarbamoyl)disulfide, dimethylthiocarbamoyl chloride and phenylchlorothiobromate, very preferably thiophosgene.

[0044] [ka]

[0045] The reactions described should be considered as illustrative only: those skilled in the art will be able to carry out corresponding modifications of the described syntheses and follow other suitable synthetic routes to obtain compounds of formula U.

[0046] The compound of formula U is preferably

[0047] [ka] teeth, [ka] where, alternatively, [ka] represents, and L 1 and L 2 are the same or different and represent F, Cl or linear, branched or cyclic alkyl or alkenyl having up to 12 C atoms, and However, other groups and parameters have the meanings given above. The compound is selected from the group consisting of:

[0048] In a preferred embodiment of the present invention, the compound of formula U is selected from the compounds of formulae U-1 to U-11.

[0049] [ka]

[0050] [ka]

[0051] During the ceremony, L 1 , L 2and L 3 are the same or different and represent H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopentenyl, and R U , X 1 , X 2 , X 3 and X 4 has the meaning given above.

[0052] According to a first aspect of the present invention, R U represents H, alkyl or alkoxy having 1 to 12 C atoms, or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12 C atoms, preferably alkyl having 1 to 12 C atoms, in which one or more CH groups are [ka] may be replaced by

[0053] According to a second aspect of the present invention, R U R P Compounds of formula U are provided, which represent, where R P is halogen, CN, NCS, R F , R F -O- or R F -S-, where R F represents a fluorinated alkyl or alkenyl having up to 9 C atoms, preferably CF3 or OCF3.

[0054] In a preferred embodiment of the invention, the medium comprises one or more compounds selected from the group of compounds of formula I, II and III.

[0055] [ka]

[0056] During the ceremony, R 1represents H, a non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms, or a non-fluorinated alkenyl, non-fluorinated alkenyloxy, or non-fluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably a non-fluorinated alkyl or non-fluorinated alkenyl, in which one or more CH groups are [ka] may be replaced by n is 0, 1 or 2; [ka] represents In the formula, R L are, identically or differently, at each occurrence, H or alkyl having 1 to 6 C atoms, preferably H, methyl or ethyl, particularly preferably H, and, however, [ka] represents When n=2, [ka] Preferably, [ka] represents More preferably, [ka] represents [ka] represents [ka]

[0057] R 2represents H, a non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms, or a non-fluorinated alkenyl, non-fluorinated alkenyloxy, or non-fluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably a non-fluorinated alkyl or non-fluorinated alkenyl, in which one or more CH groups are [ka] may be replaced by Z 21 represents trans-CH=CH-, trans-CF=CF- or -C≡C-, preferably -C≡C- or trans-CH=CH-, and [ka] represents In the formula, R L are, identically or differently, at each occurrence, H or alkyl having 1 to 6 C atoms, preferably H, methyl or ethyl, particularly preferably H, and preferably, [ka] represents Preferably, [ka] and preferably represents [ka] More preferably [ka] represents

[0058] R 3represents H, a non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms, or a non-fluorinated alkenyl, non-fluorinated alkenyloxy, or non-fluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably a non-fluorinated alkyl or non-fluorinated alkenyl, in which one or more CH groups are [ka] may be replaced by Z 31 and Z 32 On the other hand, preferably Z 32 represents trans-CH=CH-, trans-CF=CF- or -C≡C-, and the other independently represents -C≡C-, trans-CH=CH-, trans-CF=CF- or a single bond, and preferably one of them, preferably Z 32 represents -C≡C- or trans-CH=CH-, and the other represents a single bond, and [ka] represents In the formula, R L are, identically or differently, at each occurrence, H or alkyl having 1 to 6 C atoms, preferably H, methyl or ethyl, particularly preferably H, and, however, or [ka] represents Preferably [ka] represents More preferably, [ka] represents [ka] especially [ka] represents [ka] especially [ka] Represents.

[0059] In the compounds of formula I, II and III, R L preferably denotes H. In another preferred embodiment, in the compounds of formula I, II and III, one or two groups R L , preferably one group R L is different from H.

[0060] In a preferred embodiment of the present invention, the compound of formula I is selected from the group of compounds of formulae I-1 to I-5.

[0061] [ka]

[0062] During the ceremony, L 1 , L 2 and L 3 represents H or F at each occurrence, which may be the same or different, and the other groups have the respective meanings given above in formula I, Preferably R 1 represents a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms.

[0063] The medium preferably comprises one or more compounds of formula I-1, preferably selected from the group of compounds of formulae I-1a to I-1d, preferably compounds of formula I-1b.

[0064] [ka]

[0065] In the formula, R 1 has the meaning given above in formula I and preferably denotes a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms.

[0066] The medium preferably comprises one or more compounds of formula I-2, preferably selected from the group of compounds of formulae I-2a to I-2e, preferably compounds of formula I-2c.

[0067] [ka]

[0068] In the formula, R 1 has the meaning given above in formula I and preferably denotes a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms.

[0069] The medium preferably comprises one or more compounds of formula I-3, preferably selected from the group of compounds of formula I-3a to I-3d, preferably compounds of formula I-3b.

[0070] [ka]

[0071] In the formula, R 1 has the meaning given above in formula I and preferably denotes a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms.

[0072] The medium preferably comprises one or more compounds of formula I-4, preferably selected from the group of compounds of formula I-4a to I-4e, preferably compounds of formula I-4b.

[0073] [ka]

[0074] In the formula, R 1 has the meaning given above in formula I and preferably denotes a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms.

[0075] The medium preferably comprises one or more compounds of formula I-5, preferably selected from the group of compounds of formulae I-5a to I-5d, preferably compounds of formula I-5b.

[0076] [ka]

[0077] In the formula, R 1 has the meaning given above in formula I and preferably denotes a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms.

[0078] The medium preferably comprises one or more compounds of formula II, preferably selected from the group of compounds of formulae II-1 to II-3, preferably selected from the group of compounds of formulae II-1 and II-2.

[0079] [ka]

[0080] in which the occurring radicals have the meanings given above in formula II, and Preferably R 2 represents H, a non-fluorinated alkyl or alkoxy having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms, and [ka] represents The other, independently, [ka] Preferably [ka] Most preferably [ka] represents and preferably R 2 is C n H 2n+1 or CH2=CH-(CH2) Z represents, and n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0081] The compound of formula II-1 is preferably selected from the group of compounds of formulae II-1a to II-1e:

[0082] [ka]

[0083] During the ceremony, R 2 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0084] The compound of formula II-2 is preferably selected from the group of compounds of formula II-2a and II-2b:

[0085] [ka]

[0086] During the ceremony, R 2 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0087] The compound of formula II-3 is preferably selected from the group of compounds of formulae II-3a to II-3d:

[0088] [ka]

[0089] During the ceremony, R 2 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0090] The compound of formula III is preferably selected from the group of compounds of formulae III-1 to III-6, more preferably from the group of compounds of formulae III-1, III-2, III-3 and III-4, particularly preferably from the group of compounds of formulae III-1 and / or III-2.

[0091] [ka]

[0092] During the ceremony, Z 31 and Z32 are independently trans-CH=CH- or trans-CF=CF-, preferably trans-CH=CH-, or in formula III-6, Z 31 and Z 32 may represent -C≡C-, the other radical having the meaning given above in formula III, and preferably R 3 represents H, a non-fluorinated alkyl or alkoxy having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms, and [ka] Preferably [ka] represents On the other hand, independently of each other, [ka] Preferably [ka] More preferably [ka] represents However, or [ka] represents and preferably R 3 is C n H 2n+1 or CH2=CH-(CH2) Z represents n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0093] The compound of formula III-1 is preferably selected from the group of compounds of formulae III-1a to III-1k, more preferably from the group of compounds of formulae III-1a, III-1b, III-1g and III-1h, particularly preferably from the group of compounds of formulae III-1b and / or III-1h.

[0094] [ka]

[0095] [ka]

[0096] During the ceremony, R 3 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0097] The compounds of formula III-2 are preferably compounds of formulae III-2a to III-2l, very preferably III-2b and / or III-2j.

[0098] [ka]

[0099] [ka]

[0100] During the ceremony, R 3 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Zrepresents n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0101] The compounds of formula III-5 are preferably selected from the compounds of formula III-5a:

[0102] [ka]

[0103] R 3 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents n represents an integer in the range of 1 to 7, preferably 2 to 6, and particularly preferably 3 to 5.

[0104] In a preferred embodiment, the medium according to the invention comprises one or more compounds selected from the group of the compounds of the formulae IIA-1-1 to IIA-1-12, very preferably IIA-1-1 or IIA-1-2.

[0105] [ka]

[0106] [ka]

[0107] During the ceremony, R 1 represents alkyl or alkenyl having up to 7 C atoms, preferably ethyl, n-propyl, n-butyl or n-pentyl, n-hexyl, R Lare identical or different in each occurrence alkyl or alkenyl having 1 to 5 C atoms or cycloalkyl or cycloalkenyl having 3 to 6 C atoms, respectively, preferably methyl, ethyl, n-propyl, n-butyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopent-1-enyl, very preferably ethyl, and compounds of formula II-1 are excluded.

[0108] Additionally, the liquid crystal medium according to the invention in certain embodiments, which may be the same as or different from the above preferred embodiments, preferably comprises one or more compounds of formula IV.

[0109] [ka]

[0110] During the ceremony, [ka] represents s is 0 or 1, preferably 1, and Preferably [ka] Particularly preferably [ka] represents L 4 represents H or alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms or cycloalkenyl having 4 to 6 C atoms, preferably CH3, C2H5, n-C3H7, i-C3H7, cyclopropyl, cyclobutyl, cyclohexyl, cyclopent-1-enyl or cyclohex-1-enyl, and particularly preferably CH3, C2H5, cyclopropyl or cyclobutyl, X 4represents H, alkyl having 1 to 3 C atoms or halogen, preferably H, F or Cl, more preferably H or F, very particularly preferably F, R 41 ~R 44 represent independently of one another non-fluorinated alkyl or non-fluorinated alkoxy, each having 1 to 15 C atoms, non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated 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 R 43 and R 44 one or both of may also represent H; Preferably R 41 and R 42 represent, independently of one another, a non-fluorinated alkyl or a non-fluorinated alkoxy, each having 1 to 7 C atoms, or a non-fluorinated alkenyl, a non-fluorinated alkenyloxy, or a non-fluorinated alkoxyalkyl, each having 2 to 7 C atoms, Particularly preferably R 41 represents a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 7 C atoms, respectively, and Particularly preferably R 42 represents a non-fluorinated alkyl or non-fluorinated alkoxy, each having 1 to 7 C atoms, and Preferably R 43 and R 44denotes H, non-fluorinated alkyl having 1 to 5 C atoms, non-fluorinated cycloalkyl or cycloalkenyl having 3 to 7 C atoms, non-fluorinated alkylcyclohexyl or non-fluorinated cyclohexylalkyl having 4 to 12 C atoms, respectively, or non-fluorinated alkylcyclohexylalkyl having 5 to 15 C atoms, particularly preferably cyclopropyl, cyclobutyl or cyclohexyl, and very particularly preferably R 43 and R 44 At least one of these represents n-alkyl, particularly preferably methyl, ethyl or n-propyl, and the other represents H or n-alkyl, particularly preferably H, methyl, ethyl or n-propyl.

[0111] In a preferred embodiment of the present application the liquid crystal medium additionally comprises one or more compounds selected from the group of compounds of the formulae V, VI, VII, VIII and IX.

[0112] [ka]

[0113] During the ceremony, L 51 is R 51 or X 51 represents L 52 is R 52 or X 52 represents R 51 and R 52 represent, independently of one another, H, non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms or non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably alkyl or non-fluorinated alkenyl, X 51 and X 52represent, independently of one another, H, F, Cl, -CN, -NCS, -SF5, a fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or a fluorinated alkenyl, fluorinated alkenyloxy or fluorinated alkoxyalkyl having 2 to 7 C atoms, preferably a fluorinated alkoxy, a fluorinated alkenyloxy, F or Cl, and [ka] Preferably [ka]

[0114] L 61 is R 61 represents Z 61 and / or Z 62 represents trans-CH=CH- or trans-CF=CF-, and alternatively X 61 Also represents, L 62 is R 62 represents Z 61 and / or Z 62 represents trans-CH=CH- or trans-CF=CF-, and alternatively X 62 Also represents, R 61 and R 62 represent, independently of one another, H, non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms or non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably alkyl or non-fluorinated alkenyl, X 61 and X 62 represent, independently of one another, F or Cl, —CN, —SF5, fluorinated alkyl or alkoxy having 1 to 7 C atoms or fluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 7 C atoms, Z 61 and Z 62 one of them represents trans-CH=CH-, trans-CF=CF- or -C≡C-, and independently the other represents trans-CH=CH-, trans-CF=CF- or a single bond, preferably one of them represents -C≡C- or trans-CH=CH-, and the other represents a single bond; [ka] Preferably [ka] represents, and

[0115] x represents 0 or 1, L 71 is R 71 or X 71 represents L 72 is R 72 or X 72 represents R 71 and R 72 represent, independently of one another, H, non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17, preferably 3 to 10, C atoms or non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably alkyl or non-fluorinated alkenyl, X 71 and X 72 represent, independently of one another, H, F, Cl, -CN, -NCS, -SF5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl having 2 to 7 C atoms, non-fluorinated or fluorinated alkenyloxy or non-fluorinated or fluorinated alkoxyalkyl, preferably fluorinated alkoxy, fluorinated alkenyloxy, F or Cl, and Z 71 ~Z73 are independently trans-CH=CH-, trans-CF=CF-, -C≡C- or a single bond, one of which preferably represents a single bond, particularly preferably all of which represent a single bond, [ka] Preferably [ka] represents

[0116] R 81 and R 82 represent, independently of one another, H, non-fluorinated alkyl or alkoxy having 1 to 15, preferably 3 to 10, C atoms or non-fluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably non-fluorinated alkyl or alkenyl, Z 81 and Z 82 one of them represents trans-CH=CH-, trans-CF=CF- or -C≡C-, and the others independently represent trans-CH=CH-, trans-CF=CF- or a single bond, one of them preferably represents -C≡C- or trans-CH=CH-, and the other represents a single bond; and [ka] [ka] represents

[0117] L 91 is R 91 or X 91 represents L 92 is R 92 or X 92 represents R 91 and R 92represent, independently of one another, H, non-fluorinated alkyl or alkoxy having 1 to 15, preferably 3 to 10, C atoms or non-fluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably non-fluorinated alkyl or alkenyl, X 91 and X 92 represent, independently of one another, H, F, Cl, -CN, -NCS, -SF5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl having 2 to 7 C atoms, non-fluorinated or fluorinated alkenyloxy or non-fluorinated or fluorinated alkoxyalkyl, preferably fluorinated alkoxy, fluorinated alkenyloxy, F or Cl, and Z 91 ~Z 93 are independently trans-CH=CH-, trans-CF=CF-, -C≡C- or a single bond, one of which preferably represents a single bond, particularly preferably all of which represent a single bond, [ka] [ka] Represents.

[0118] In a preferred embodiment of the invention the liquid crystal medium comprises one or more compounds selected from the group of compounds of formula V, preferably of formulae V-1 to V-3, preferably of formulae VI-1 and / or V-2 and / or V-3, preferably of formulae V-1 and V-2

[0119] [ka]

[0120] wherein the parameters each have the meanings given in Formula V above, preferably R 51represents a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms, R 52 represents a non-fluorinated alkyl having 1 to 7 C atoms or a non-fluorinated alkenyl having 2 to 7 C atoms or a non-fluorinated alkoxy having 1 to 7 C atoms, X 51 and X 52 are each independently F, Cl, —OCF3, —CF3, —CN, —NCS or —SF5, preferably F, Cl, —OCF3 or —CN. The compounds of formula V-1 are preferably selected from the group of compounds of formulae V-1a to V-1d, preferably of formulae V-1c and V-1d:

[0121] [ka]

[0122] wherein the parameters each have the meanings given above in Formula V-1, except that Y 51 and Y 52 represent in each case independently of one another H or F, and preferably R 51 represents alkyl or alkenyl with up to 7 C atoms, and X 51 represents F, Cl or -OCF3. The compound of formula V-2 is preferably selected from the group of compounds of formulae V-2a to V-2e and / or from the group of compounds of formulae V-2f and V-2g.

[0123] [ka]

[0124] In each case, compounds of formula V-2a are excluded from compounds of formula V-2b and V-2c, compounds of formula V-2b are excluded from compounds of formula V-2c, compounds of formula V-2f are excluded from compounds of formula V-2g, and wherein the parameters each have the meanings set forth above in Equation V-1, Y 51 and Y 52 represent in each case independently of one another H or F, and preferably Y 51 and Y 52 denote in each case independently of one another H or F, preferably H as well.

[0125] The compound of formula V-3 is preferably a compound of formula V-3a:

[0126] [ka]

[0127] wherein the parameters each have the meanings given in formula V-1 above, but preferably X 51 represents F, Cl, preferably F, X 52 represents F, Cl or —OCF3, preferably —OCF3.

[0128] The compound of formula V-1a is preferably selected from the group of compounds of formula V-1a-1 and V-1a-2:

[0129] [ka]

[0130] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 where n represents an integer in the range of 1 to 7, preferably 2 to 6, and particularly preferably 3 to 5.

[0131] The compound of formula V-1b is preferably a compound of formula V-1b-

[0132] [ka]

[0133] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 where n represents an integer in the range of 1 to 7, preferably 2 to 6, and particularly preferably 3 to 5.

[0134] The compound of formula V-1c is preferably selected from the group of compounds of formulae V-1c-1 to V-1c-4, particularly preferably selected from the group of compounds of formulae V-1c-1 and V-1c-2.

[0135] [ka]

[0136] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 where n represents an integer in the range of 1 to 7, preferably 2 to 6, and particularly preferably 3 to 5.

[0137] The compound of the formula V-1d is preferably selected from the group of the compounds of the formulae V-1d-1 and V-1d-2, particularly preferably the compound of the formula V-1d-2.

[0138] [ka]

[0139] During the ceremony, R 51has the meaning given above, preferably C n H 2n+1 where n represents an integer in the range of 1 to 7, preferably 2 to 6, and particularly preferably 3 to 5.

[0140] The compound of the formula V-2a is preferably selected from the group of the compounds of the formulae V-2a-1 and V-2a-2, particularly preferably the compound of the formula V-2a-1.

[0141] [ka]

[0142] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 52 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0143] In particular, in the case of formula V-2a-1 (R 51 and R 52 ) is preferably a combination of (C n H 2n+1 and C m H 2m+1 ), (C n H 2n+1 and O.C. m H 2m+1 ), (CH2=CH-(CH2) Z and C m H 2m+1), (CH2=CH-(CH2) Z and O.C. m H 2m+1 ) and (C n H 2n+1 and (CH2) Z -CH=CH2).

[0144] A preferred compound of formula V-2b is a compound of formula V-2b-1.

[0145] [ka]

[0146] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 52 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0147] where (R 51 and R 52 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 )

[0148] A preferred compound of formula V-2c is a compound of formula V-2c-1:

[0149] [ka]

[0150] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 52 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0151] where (R 51 and R 52 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 )

[0152] A preferred compound of formula V-2d is a compound of formula V-2d-1:

[0153] [ka]

[0154] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 52 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2)Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0155] where (R 51 and R 52 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 )

[0156] A preferred compound of formula V-2e is a compound of formula V-2e-1.

[0157] [ka]

[0158] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 52 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0159] where (R 51 and R 52 ) is particularly preferably a combination of (C n H 2n+1 and O.C. m H 2m+1)

[0160] A preferred compound of formula V-2f is a compound of formula V-2f-1:

[0161] [ka]

[0162] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 52 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0163] where (R 51 and R 52 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H 2m+1 )

[0164] A preferred compound of formula V-2g is a compound of formula V-2g-1.

[0165] [ka]

[0166] During the ceremony, R 51 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 52 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0167] where (R 51 and R 52 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and O.C. m H 2m+1 )

[0168] The compound of formula VI is preferably selected from the group of compounds of formulae VI-1 to VI-5:

[0169] [ka]

[0170] During the ceremony, Z 61 and Z 62represents -C≡C-, trans-CH=CH- or trans-CF=CF-, preferably -C≡C- or trans-CH=CH-, and other occurring groups and parameters have the meanings given above in formula VI, preferably R 61 and R 62 represent, independently of one another, H, non-fluorinated alkyl or alkoxy having 1 to 7 C atoms or non-fluorinated alkenyl having 2 to 7 C atoms, X 62 represents F, Cl, -OCF3 or -CN.

[0171] The compound of formula VI-1 is preferably selected from the group of compounds of formula VI-1a and VI-1b, more preferably selected from the group of compounds of formula VI-1a.

[0172] [ka]

[0173] During the ceremony, R 61 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 62 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0174] In this specification, (R 61 and R 62 ) is particularly preferred combination of (C n H2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), and in the case of formula U-1a, particularly preferably (C n H 2n+1 and C m H 2m+1 ), and in the case of formula U-1b, it is particularly preferably (C n H 2n+1 and O.C. m H 2m+1 )

[0175] The compound of formula VI-3 is preferably selected from the compounds of formulae VI-3a to VI-3e:

[0176] [ka]

[0177] wherein the parameters have the meanings given above in formula VI-3, preferably R 61 has the meaning given above, preferably C n H 2n+1 where n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and X 62 represents -F, -Cl, -OCF3 or -CN.

[0178] The compound of formula VI-4 is preferably selected from the compounds of formulae VI-4a to VI-4e:

[0179] [ka]

[0180] wherein the parameters have the meanings given above in formula VI-4, preferably R 61has the meaning given above, preferably C n H 2n+1 where n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and X 62 represents -F, -Cl, -OCF3 or -CN.

[0181] The compounds of formula VI-5 are preferably selected from the compounds of formulae VI-5a to VI-5d, preferably VI-5b:

[0182] [ka]

[0183] wherein the parameters have the meanings given above in formula VI-5, preferably R 61 has the meaning given above, preferably C n H 2n+1 where n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and X 62 represents -F, -Cl, -OCF3 or -CN, particularly preferably -OCF3.

[0184] The compound of formula VII is preferably selected from the group of compounds of formulae VII-1 to VII-6:

[0185] [ka]

[0186] provided that compounds of formula VII-5 are excluded from compounds of formula VII-6, and wherein the parameters each have the meanings set forth above in Formula VII; Y 71 , Y 72 , Y 73 represent independently of one another H or F, and Preferably R 71 represents a non-fluorinated alkyl or alkoxy, each having 1 to 7 C atoms, or a non-fluorinated alkenyl having 2 to 7 C atoms, R 72 represents a non-fluorinated alkyl or alkoxy, each having 1 to 7 C atoms, or a non-fluorinated alkenyl having 2 to 7 C atoms, and X 72 represents F, Cl, NCS or -OCF3, preferably F or NCS, and Particularly preferably, R 71 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 72 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 15, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0187] The compound of formula VII-1 is preferably selected from the group of compounds of formulae VII-1a to VII-1d:

[0188] [ka]

[0189] X in the formula 72 has the meaning given above in formula VII-2, and R 71 has the meaning given above, preferably C n H 2n+1 where n represents 1 to 7, preferably 2 to 6, particularly preferably 2, 3 or 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2, and X 72 preferably represents F.

[0190] The compounds of the formula VII-2 are preferably selected from the group of the compounds of the formulae VII-2a and VII-2b, particularly preferably of the formula VII-2a.

[0191] [ka]

[0192] During the ceremony, R 71 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 72 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0193] where (R 71 and R 72 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H2m+1 )

[0194] The compound of formula VII-3 is preferably a compound of formula VII-3a.

[0195] [ka]

[0196] During the ceremony, R 71 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 72 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0197] where (R 71 and R 72 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H 2m+1 )

[0198] The compound of formula VII-4 is preferably a compound of formula VII-4a:

[0199] [ka]

[0200] During the ceremony, R 71 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 72 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0201] where (R 71 and R 72 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H 2m+1 )

[0202] The compound of formula VII-5 is preferably selected from the group of compounds of formula VII-5a and VII-5b, more preferably of formula VII-5a.

[0203] [ka]

[0204] During the ceremony, R 71has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 72 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0205] where (R 71 and R 72 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H 2m+1 )

[0206] The compound of formula VII-6 is preferably selected from the group of compounds of formula VII-6a and VII-6b:

[0207] [ka]

[0208] During the ceremony, R 71 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 72 has the meaning given above, preferably Cm H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0209] where (R 71 and R 72 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H 2m+1 )

[0210] The compound of formula VII-7 is preferably selected from the group of compounds of formulae VII-7a to VII-7d:

[0211] [ka]

[0212] During the ceremony, R 71 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents X 72 represents F, -OCF3 or -NCS, n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0213] The compounds of formula VIII are preferably selected from the group of compounds of formulae VIII-1 to VIII-3, more preferably these compounds of formula VIII consist mainly, even more preferably consist essentially and very particularly preferably consist completely thereof.

[0214] [ka]

[0215] During the ceremony, Y 81 and Y 82 one of represents H and the other represents H or F, and R 81 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 82 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0216] where (R 81 and R 82 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H 2m+1 )

[0217] The compound of formula VIII-1 is preferably selected from the group of compounds of formulae VIII-1a to VIII-1c:

[0218] [ka]

[0219] During the ceremony, R 81 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 82 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0220] where (R 81 and R 82 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H 2m+1 )

[0221] The compound of formula VIII-2 is preferably a compound of formula VIII-2a.

[0222] [ka]

[0223] During the ceremony, R 81 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 82 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0224] where (R 81 and R 82 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ), (C n H 2n+1 and O.C. m H 2m+1 ) and (CH2=CH-(CH2) Z and C m H 2m+1 ), particularly preferably (C n H 2n+1 and C m H 2m+1 )

[0225] The compound of formula VIII-3 is preferably a compound of formula VIII-3a.

[0226] [ka]

[0227] During the ceremony, R 81 has the meaning given above, preferably Cn H 2n+1 or CH2=CH-(CH2) Z represents, and R 82 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0228] where (R 81 and R 82 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 )

[0229] The compound of formula IX is preferably selected from the group of compounds of formulae IX-1 to IX-3:

[0230] [ka]

[0231] wherein the parameters each have the meanings given in formula IX above, preferably [ka] and wherein R 91 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 92has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0232] where (R 91 and R 92 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 )

[0233] The compound of formula IX-1 is preferably selected from the group of compounds of formulae IX-1a to IX-1e:

[0234] [ka]

[0235] wherein the parameters have the meanings given above, preferably R 91 has the meaning given above, preferably C n H 2n+1 represents, and n represents an integer in the range of 1 to 7, preferably 2 to 6 and particularly preferably 3 to 5, and X 92 preferably represents F or Cl.

[0236] The compound of formula IX-2 is preferably selected from the group of compounds of formulae IX-2a and IX-2b:

[0237] [ka]

[0238] During the ceremony, R 91 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 92 has the meaning given above, preferably C m H 2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0239] where (R 91 and R 92 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 )

[0240] The compound of formula IX-3 is preferably selected from the group of compounds of formulae IX-3a and IX-3b:

[0241] [ka]

[0242] During the ceremony, R 91 has the meaning given above, preferably C n H 2n+1 or CH2=CH-(CH2) Z represents, and R 92 has the meaning given above, preferably C m H2m+1 or O.C. m H 2m+1 or (CH2) Z represents -CH=CH2, n and m each independently represent an integer in the range of 1 to 7, preferably in the range of 2 to 6 and particularly preferably in the range of 3 to 5, and z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0243] where (R 91 and R 92 ) is particularly preferably a combination of (C n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and O.C. m H 2m+1 ), particularly preferably (C n H 2n+1 and O.C. m H 2m+1 )

[0244] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula X:

[0245] [ka]

[0246] During the ceremony, R 101 represents H, alkyl or alkoxy having 1 to 15, preferably 3 to 10, C atoms or non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15, preferably 3 to 10, C atoms, preferably alkyl or alkenyl, X 101represents H, F, Cl, —CN, SF5, NCS, a fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or a fluorinated alkenyl, fluorinated alkenyloxy or fluorinated alkoxyalkyl having 2 to 7 C atoms, preferably a fluorinated alkoxy, fluorinated alkenyloxy, F, Cl or NCS, particularly preferably NCS, Y 101 represents methyl, ethyl or Cl, Y 102 represents H, methyl, ethyl, F or Cl, preferably H or F, Z 101 , Z 102 are the same or different and represent a single bond, -CH=CH-, -CF=CF- or -C≡C-; [ka] Preferably [ka] represents, and, however, or [ka] represents n is 0 or 1.

[0247] Preferably, the compound of formula X is selected from sub-formulae X-1 and X-2.

[0248] [ka]

[0249] wherein the occurring groups and parameters have the meanings given above for formula X.

[0250] Particularly preferably, the medium according to the invention comprises one or more compounds selected from the group of compounds of the formulae X-1-1 to X-1-9.

[0251] [ka]

[0252] In a preferred embodiment, the medium according to the invention comprises one or more compounds of formula XI.

[0253] [ka]

[0254] During the ceremony, R S represents 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 are [ka] wherein one or more H atoms may be replaced by F; [ka] represents In the formula, R L are identical or different at each occurrence and represent H, Cl or linear, branched or cyclic alkyl having 1 to 6 C atoms, L S1 , L S2 are the same or different and represent H, Cl or F; R S1 , R S2 are the same or different and represent H, alkyl or alkenyl having up to 6 C atoms or cyclopropyl, cyclobutyl, cyclopentenyl or cyclopentyl, R Th1 , R Th2 are the same or different and represent H, alkyl or alkenyl or alkoxy having up to 6 C atoms or cyclopropyl, cyclobutyl, cyclopentenyl or cyclopentyl, Z S1 , ZS2 , Z S3 are the same or different and represent -CH=CH-, -CH=CF-, -CF=CH-, -CF=CF-, -C≡C- or a single bond; a and b are the same or different and each is 0 or 1.

[0255] Preferably, the compound of formula XI is selected from the group of compounds of formula XI-1 to formula XI-24.

[0256] [ka]

[0257] [ka]

[0258] [ka]

[0259] [ka]

[0260] in which the occurring radicals have the meanings given above for formula XI, preferably R S represents an alkyl or alkenyl having 2 to 6 C atoms, in which one or more CH2 groups are [ka] may be replaced by R S1 and R S2 are the same or different and represent H or alkyl having 1 to 6 C atoms, preferably H, R S3 represents H, F or alkyl having up to 6 C atoms or cyclopropyl, preferably H, F or ethyl, very preferably H, LS1 and L S2 are the same or different and represent H or F, preferably F.

[0261] Preferably, the medium according to the invention comprises one or more compounds of formula T

[0262] [ka]

[0263] During the ceremony, R T is halogen, CN, NCS, R F , R F -O- or R F -S-, where R F represents a fluorinated alkyl or alkenyl having up to 12 C atoms, [ka] represents L 4 and L 5 are the same or different and represent F, Cl or linear, branched or cyclic alkyl or alkenyl having up to 12 C atoms, Z T3 , Z T4 are the same or different and represent -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C- or a single bond, and t is 0 or 1.

[0264] In a preferred embodiment, the liquid crystal medium according to the invention comprises one or more compounds selected from the group of compounds of the following formulae T-1a to T-3b:

[0265] [ka]

[0266] During the ceremony, [ka] has the meaning given above, and n is 1, 2, 3, 4, 5, 6 or 7, preferably 1, 2, 3 or 4, particularly preferably 1.

[0267] In a particularly preferred embodiment of the invention, the medium comprises one or more compounds selected from the compounds of formula T-1a and formula T-2a:

[0268] Preferred compounds of formula T-1a are selected from the group of compounds of the following subformulae:

[0269] [ka]

[0270] In the formula, n is 1, 2, 3 or 4, preferably 1.

[0271] Preferred compounds of formula T-2a are selected from the group of compounds of the following subformulae:

[0272] [ka]

[0273] In the formula, n is 1, 2, 3 or 4, preferably 1.

[0274] Very preferably, the medium according to the invention comprises one or more compounds of formula T-1a-5.

[0275] In one embodiment, the medium according to the invention comprises a group R 1 , R 2 , R 3 , R 41 , R 42 , R 51 , R 52 , R 61 , R 62 , R 71 , R 72 , R 81 , R82 , R 91 , R 92 , R 101 , R 102 and R S and X are each a cyclic alkyl group.

[0276] As used herein, cyclic alkyl is understood to refer to a linear or branched alkyl or alkenyl having up to 12 C atoms, preferably an alkyl having 1 to 7 C atoms, in which the group CH2 is replaced by a carbocyclic ring having 3 to 5 C atoms, very preferably selected from the group consisting of cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl and cyclopentenylalkyl.

[0277] Highly preferred compounds containing a cyclic alkyl group are selected from compounds of formulae Cy-1 to Cy-14:

[0278] [ka]

[0279] [ka]

[0280] The medium according to the invention comprises one or more chiral dopants. Preferably, these chiral dopants are -1 ~150μm -1 range, preferably 10 μm -1 ~100μm -1The absolute value of the helical twisting power (HTP) is in the range of . If the medium contains two or more chiral dopants, they may have opposite signs of their HTP values. This condition is preferred for some specific embodiments, since it allows the chirality of each compound to be compensated to some extent, and can thus be used to compensate for the various temperature-dependent properties of the resulting medium in the device. However, it is generally preferred that most, preferably all, of the chiral compounds present in the medium according to the present invention have the same sign of their HTP values.

[0281] Preferably, the chiral dopants present in the media according to the present application are mesogenic compounds, most preferably they alone exhibit a mesophase.

[0282] In a preferred embodiment of the present invention, the medium comprises two or more chiral compounds that all have the same algebraic sign of the HTP.

[0283] The temperature dependence of the HTP of individual compounds can be high or low. The temperature dependence of the pitch of the medium can be compensated for by mixing compounds with different temperature dependences of the HTP in corresponding ratios.

[0284] For optically active components, a large number of chiral dopants, some of which are commercially available, are available to those skilled in the art, such as, for example, cholesteryl nonanoate, R- and S-811, R- and S-1011, R- and S-2011, R- and S-3011, R- and S-4011, or CB15 (all Merck, Darmstadt).

[0285] Particularly suitable dopants are compounds which contain one or more chiral groups and one or more mesogenic groups, or one or more aromatic or alicyclic groups which together with the chiral groups form a mesogenic group.

[0286] Suitable chiral groups are, for example, monovalent or polyvalent chiral groups selected from the group consisting of chiral branched hydrocarbon groups, chiral ethanediols, binaphthols or dioxolanes, also sugar derivatives, sugar alcohols, sugar acids, lactic acid, chiral substituted glycols, steroid derivatives, terpene derivatives, amino acids or sequences of several, preferably 1 to 5, amino acids.

[0287] Preferred chiral groups are sugar derivatives, such as glucose, mannose, galactose, fructose, arabinose and dextrose; sugar alcohols, such as sorbitol, mannitol, iditol, galactitol or their anhydro derivatives, in particular dianhydrohexitols, such as dianhydrosorbide (1,4:3,6-dianhydro-D-sorbide, isosorbide), dianhydromannitol (isosorbitol) or dianhydroiditol (isoiditol); sugar acids, such as gluconic acid, gulonic acid and ketogulonic acid; chiral substituted glycol groups. , such as mono- or oligoethylene or propylene glycols in which one or more CH2 groups are substituted by alkyl or alkoxy; amino acids, such as alanine, valine, phenylglycine or phenylalanine, or a sequence of 1 to 5 of these amino acids; steroid derivatives, such as cholesteryl or cholic acid groups; terpene derivatives, such as menthyl, neomenthyl, campheyl, pineyleyl, terpineyl, isolongifolyl, fenchyl, careyl, myrtenyl, nopyr, geranyl, linaloyl, neryl, citronellyl or dihydrocitronellyl.

[0288] The medium according to the present invention preferably comprises chiral dopant that is selected from the group of known chiral dopants.Suitable chiral group and mesogenic chiral compound are described, for example, in German Patent No. 3425503, German Patent No. 3534777, German Patent No. 3534778, German Patent No. 3534779 and German Patent No. 3534780, German Patent No. 4342280, European Patent No. 01038941 and German Patent No. 19541820.Also examples are the compounds listed in table F below.

[0289] Chiral compounds preferably used in accordance with the present invention are selected from the group consisting of the formulae shown below:

[0290] Particularly preferred are chiral dopants selected from the group consisting of compounds of the following formulae AI to A-III and A-Ch:

[0291] [ka]

[0292] During the ceremony, R a11 , R a12 and R b12 represent, independently of one another, alkyl having 1 to 15 C atoms, where, furthermore, one or more non-adjacent CH groups may be, independently of one another, —C(R z )=C(R z )-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, wherein further one or more H atoms may be replaced by F, Cl, Br, I or CN; Preferably, it represents alkyl, more preferably n-alkyl, provided that R a12 is R b12 Unlike, R a21 and R a22represent, independently of one another, alkyl having 1 to 15 C atoms, where, furthermore, one or more non-adjacent CH groups may be, independently of one another, —C(R z )=C(R z )-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, wherein further one or more H atoms may be replaced by F, Cl, Br, I or CN; Preferably, both represent alkyl, more preferably n-alkyl; R a31 , R a32 and R b32 represent, independently of one another, a straight-chain or branched alkyl having 1 to 15 C atoms, wherein further, one or more non-adjacent CH groups may be joined independently of one another by a -C(R z )=C(R z )-, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, wherein further one or more H atoms may be replaced by F, Cl, Br, I or CN; Preferably, it represents alkyl, more preferably n-alkyl, provided that R a32 is R b32 Unlike, R z represents H, CH3, F, Cl or CN, preferably H or F, R 8 is the R given above a11 preferably alkyl having 1 to 15 C atoms, more preferably n-alkyl, Z 8 represents —C(O)O—, —CHO—, —CFO— or a single bond, preferably —C(O)O—, A 11 is below A 12 or [ka] represents A 12 teeth, [ka] Preferably [ka] represents During the ceremony, L 12 represent, in each occurrence independently of one another, halogen, CN, or alkyl, alkenyl, alkoxy or alkenyloxy having up to 12 C atoms, with the proviso that one or more H atoms may be replaced by halogen, preferably methyl, ethyl, Cl or F, particularly preferably F. A 21 teeth, [ka] represents A 22 is A 12 has the meaning given to A 31 is A 11 has the meaning given to [ka] represents A 32 is A 12 has the meaning given to n2 is, identically or differently, 0, 1, or 2 in each occurrence; n3 is 1, 2 or 3; r is 0, 1, 2, 3 or 4.

[0293] Particularly preferred are dopants selected from the group consisting of compounds of the following formulae:

[0294] [ka]

[0295] [ka]

[0296] During the ceremony, m, which may be the same or different in each occurrence, is an integer from 1 to 9; and n is the same or different in each occurrence and is an integer from 2 to 9.

[0297] A particularly preferred compound of formula A is the compound of formula A-III:

[0298] Further preferred dopants are derivatives of isosorbide, isomannitol or isoiditol of formula A-IV below.

[0299] [ka]

[0300] In the formula, the group [ka] teeth, [ka] and preferably dianhydrosorbitol.

[0301] and chiral ethanediols, such as diphenylethanediol (hydrobenzoin), in particular mesogenic hydrobenzoin derivatives of formula AV below, including the (S,S) enantiomer not shown.

[0302] [ka]

[0303] During the ceremony, [ka] 1,4-phenylene or 1,4-cyclohexylene, each of which may be mono-, di- or trisubstituted by L; L is H, F, Cl, CN, or optionally halogenated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkoxycarbonyloxy having 1 to 7 carbon atoms; c is 0 or 1, X is CH2 or -C(O)-; Z 0 is -COO-, -OCO-, -CH2CH2- or a single bond, R 0 is alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl or alkylcarbonyloxy having 1 to 12 carbon atoms.

[0304] Examples of compounds of formula IV are:

[0305] [ka]

[0306] [ka]

[0307] Compounds of formula A-IV are described in WO 98 / 00428. Compounds of formula AV are described in GB 2,328,207.

[0308] Highly particularly preferred dopants are the chiral binaphthyl derivatives described in WO 02 / 94805, the chiral binaphthol acetal derivatives described in WO 02 / 34739, the chiral TADDOL derivatives described in WO 02 / 06265, and the chiral dopants having at least one fluorinated bridging group and a terminal or central chiral group described in WO 02 / 06196 and WO 02 / 06195.

[0309] Chiral compounds of formula A-VI are particularly preferred.

[0310] [ka]

[0311] During the ceremony, X 1 , X 2 , Y 1 and Y 2 are each, independently of one another, F, Cl, Br, I, CN, SCN, SF, linear or branched alkyl having 1 to 25 carbon atoms (which may be mono- or polysubstituted with F, Cl, Br, I or CN, and in addition, one or more non-adjacent CH groups are each, independently of one another, -O-, -S-, -NH-, NR, such that O and / or S atoms are not directly bonded to one another; 0 -, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C-), a polymerizable group or a cycloalkyl or aryl having up to 20 carbon atoms, which may be optionally mono- or polysubstituted by halogen, preferably F, or by a polymerizable group, x 1 and x 2 are each independently 0, 1 or 2, y 1 and y 2 are each independently 0, 1, 2, 3 or 4, B 1 and B 2 are each, independently of one another, an aromatic or partially saturated or fully saturated aliphatic six-membered ring, in which one or more CH groups are each optionally replaced by an N atom, and one or more non-adjacent CH groups are each optionally replaced by O and / or S, W 1 and W 2 are each independently of the other, -Z 1 -A 1 -(Z2 -A 2 ) m -R, or one of the two is R 1 or A 3 but not both at the same time, or [ka] teeth, [ka] and U 1 and U 2 are each independently CH, O, S, CO or CS, V 1 and V 2 are each independently (CH2) n (wherein 1 to 4 non-adjacent CH groups may be replaced by O and / or S), and V 1 and V 2 One of them is [ka] but, [ka] are both single bonds, n is 1, 2 or 3; Z 1 and Z 2 are each independently -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, or -CO-NR 0 -, -NR 0-CO-, -O-CH2-, -CH2-O-, -S-CH2-, -CH2-S-, -CF2-O-, -O-CF2-, -CF2-S-, -S-CF2-, -CH2-CH2-, -CF2-CH2-, -CH2-CF2-, -CF2-CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, a combination of two of these groups (wherein two O and / or S and / or N atoms are not directly bonded to each other), (preferably -CH=CH-COO- or -COO-CH=CH-), or a single bond, R x represents alkyl having 1 to 6 C atoms, A 1 , A 2 and A 3 are each independently 1,4-phenylene in which one or two non-adjacent CH groups may be replaced by N, 1,4-cyclohexylene in which one or two non-adjacent CH groups may be replaced by O and / or S, 1,3-dioxolane-4,5-diyl, 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl (each of these groups may be mono- or polysubstituted by L), and further A 1 can be a single bond, L is a halogen atom, preferably F, CN, NO, alkyl having 1 to 7 carbon atoms, alkoxy, alkylcarbonyl, alkoxycarbonyl or alkoxycarbonyloxy (wherein one or more H atoms may be replaced by F or Cl), m is independently 0, 1, 2, or 3; R and R 1are each independently H, F, Cl, Br, I, CN, SCN, SF5, straight-chain or branched alkyl having 1 or 3 to 25 carbon atoms (which may be mono- or polysubstituted with F, Cl, Br, I or CN), and one or more non-adjacent CH2 groups may be -O-, -S-, -NH-, -NR2-, -NR3-, -NR4-, -NR5-, -NR6-, -NR7-, -NR8-, -NR9-, -NR10-, -NR11-, -NR12-, -NR13-, -NR14-, -NR15-, -NR16-, -NR17-, -NR18-, -NR19-, -NR20-, -NR21-, -NR22-, -NR23-, -NR24-, -NR25-, -NR26-, -NR27-, -NR28-, -NR29-, -NR30-, -NR31-, -NR32-, -NR33-, -NR44-, -NR45-, -NR46-, -NR47-, -NR48-, -NR59-, -NR50-, -NR51-, -NR52-, -NR53-, -NR54-, -NR55-, -NR56-, -NR57-, -NR58-, -NR59 ...0-, -NR51-, -NR51-, -NR52-, -NR53-, -NR54-, -NR55-, -NR56-, -NR57-, -NR58-, -NR59-, -NR59-, -NR59-, -NR 0 -, -CO-, -COO-, -OCO-, -O-COO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C-), or a polymerizable group.

[0312] Chiral binaphthyl derivatives of formula A-VI-1 are particularly preferred.

[0313] [ka]

[0314] In the formula, rings B, R 0 and Z 0 is as defined for Formulas A-IV and AV, and b is 0, 1, or 2.

[0315] In particular, they are selected from the following formulae A-VI-1a to A-VI-1c:

[0316] [ka]

[0317] In the formula, rings B, R 0 and Z 0 is as defined for formula A-VI-1, R 0 is as defined for formula A-IV, or is H or alkyl having 1 to 4 carbon atoms; b is 0, 1 or 2; Z 0 is in particular -OC(O)- or a single bond.

[0318] The concentration of one or more chiral dopants (single or multiple) in the LC medium is preferably in the range of 0.001% to 20%, preferably 0.05% to 5%, more preferably 0.1% to 2%, and most preferably 0.5% to 1.5%. These preferred concentration ranges apply in particular to chiral dopants S-4011 or R-4011 (both from Merck) and chiral dopants with the same or similar HTP. For chiral dopants with higher or lower absolute HTP values ​​compared to S-4011, these preferred concentrations should be proportionally reduced or increased, respectively, according to the ratio of their HTP value to that of S-4011.

[0319] The pitch p of the LC media or host mixtures according to the invention is preferably in the range from 5 to 50 μm, more preferably from 8 to 30 μm, particularly preferably from 10 to 20 μm.

[0320] Preferably, the medium according to the invention comprises a stabilizer selected from the group of compounds of the formulae ST-1 to ST-18.

[0321] [ka]

[0322] [ka]

[0323] [ka]

[0324] [ka] During the ceremony, R STrepresents H, alkyl or alkoxy having 1 to 15 C atoms, wherein, further, one or more non-adjacent CH groups in these groups may each independently be -C≡C-, -CF2O-, -OCF2-, -CH=CH-, ... [ka] -O-, -CO-O- or -O-CO-O-, wherein further, one or more H atoms may be replaced by halogen; [ka] [ka] represents Z ST represent, independently of one another, -CO-O-, -O-CO-, -CF2O-, -OCF2-, -C2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CHO-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond; L 1 and L 2 each independently represent F, Cl, CF3 or CHF2, p is 1 or 2; q is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0325] Among the compounds of formula ST, the compounds of formula:

[0326] [ka]

[0327] [ka]

[0328] [ka]

[0329] In the compounds of formulae ST-3a and ST-3b, n preferably represents 3. In the compounds of formula ST-2a, n preferably represents 7.

[0330] Very particularly preferred mixtures according to the invention comprise one or more stabilizers from the group of the compounds of the formulae ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1 and ST-12.

[0331] [ka]

[0332] [ka]

[0333] The compounds of the formulae ST-1 to ST-18 are preferably each present in the liquid crystal mixture according to the invention in an amount of 0.005 to 0.5%, based on the mixture.

[0334] If the mixture according to the invention comprises two or more compounds from the group of compounds of formulae ST-1 to ST-18, then the concentration increases to 0.01 to 1% for two compounds, correspondingly, based on the mixture.

[0335] However, the total proportion of compounds of the formulae ST-1 to ST-18, based on the mixture according to the invention, should not exceed 2%.

[0336] The compounds according to the invention can be synthesized by known methods described in the literature (e.g., standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart, etc.) under known reaction conditions suitable for the reaction in question. Modifications known per se but not mentioned here can also be used herein. In particular, they can be prepared as described in the following reaction schemes or in analogy thereto. Further methods for preparing the compounds of the invention can be seen from the examples.

[0337] Other mesogenic compounds not explicitly mentioned above can also optionally be used advantageously in the media according to the invention, such compounds being known to those skilled in the art.

[0338] In a preferred embodiment of the invention the total concentration of compounds of formula U in the liquid crystal medium is at least 5%, preferably at least 8%, very preferably at least 10% and particularly preferably at least 12%.

[0339] In a preferred embodiment of the invention, the liquid-crystalline medium comprises in total 5% to 40%, preferably 10% to 35%, particularly preferably 15% to 30%, of compounds of the formula U.

[0340] In a preferred embodiment of the invention, the liquid-crystalline medium comprises a total of 10% to 45%, preferably 15% to 40%, particularly preferably 20% to 35% of compounds of the formula T, preferably selected from the formulae T-1a and T-2a, very preferably from T-1a-5 and T-2a-4.

[0341] In a preferred embodiment of the invention, the liquid-crystalline medium comprises in total 5% to 35%, preferably 10% to 30%, particularly preferably 15% to 25%, of compounds of the formula T-1a.

[0342] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formula I, preferably formula I-2, in a total concentration ranging from 1% to 25%, more preferably from 2% to 20%, particularly preferably from 5% to 15%.

[0343] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula I-3 in a total concentration ranging from 1% to 20%, more preferably from 2% to 15%, particularly preferably from 3% to 10%.

[0344] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formula II, preferably formula II-1, in a total concentration ranging from 5% to 35%, more preferably from 10% to 30%, particularly preferably from 15% to 25%.

[0345] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula IIA-1 in a total concentration of 5% to 25%, more preferably 8% to 20%, particularly preferably 10% to 15%.

[0346] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula II-1 in a total concentration of not more than 30%, more preferably not more than 25%, particularly preferably not more than 20%.

[0347] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula III, preferably III-1 and / or III-2, more preferably III-1h and / or III-1b, in a total concentration of 15% to 70%, more preferably 25% to 60%, particularly preferably 35% to 50%.

[0348] Further preferred embodiments of the present invention, alone or in combination with each other, are as follows, where some compounds are abbreviated using the acronyms shown in Table C below:

[0349] The medium comprises one, two, three, four or more compounds selected from compounds of formula III-1, preferably compounds of formula III-1b, III-1f and III-1h, more preferably compounds of formula III-1b and III-1h.

[0350] The medium preferably comprises the compound of formula III-1b in a total concentration ranging from 2% to 30%, more preferably from 5% to 25%, in particular from 10% to 20%.

[0351] The medium preferably comprises the compound of formula III-1h in a total concentration ranging from 10% to 40%, more preferably from 15% to 35%, in particular from 20% to 30%.

[0352] The medium comprises the compounds PPU-TO-S and / or PPTU-TO-S and / or PTPU-TO-S and / or PP(1)TO-nS.

[0353] The medium preferably comprises one or more compounds of formula U and one or more compounds of formula II-1 and / or one or more compounds of formula IIA-1 in a total concentration ranging from 25% to 45%, in particular from 30% to 40%.

[0354] The medium comprises one or more compounds of formula I-2d, preferably the compounds PGU-2-S and / or PGU-3-S and / or PGU-4-S.

[0355] The medium comprises one or more compounds of the formula I-2d and II-1b, preferably the compounds PGU-3-S and / or PGU-4-S and PTU-3-S and / or PTU-4-S and / or PTU-5-S.

[0356] The medium comprises one or more compounds of formula PPTU-nS and / or PTPU-nS in a total concentration ranging from 10 to 20%.

[0357] The medium comprises one or more compounds of formula PPTU-nS and / or PTPU-nS and / or PGTU-nS in a total concentration ranging from 15 to 30%.

[0358] The medium comprises one or more compounds of formula ST-3, preferably ST-3a and / or ST-3b, particularly preferably ST-3b-1, in a total concentration in the range of 0.01 to 1%, preferably 0.05 to 0.5%, in particular 0.10 to 0.15%.

[0359] The liquid-crystalline media according to the present invention preferably have a clearing point of 90°C or higher, more preferably 100°C or higher, even more preferably 110°C or higher, more preferably 120°C or higher, even more preferably 130°C or higher, particularly preferably 140°C or higher, and very particularly preferably 150°C or higher.

[0360] The liquid-crystalline media according to the invention preferably have a clearing point of 160°C or less, more preferably 140°C or less, particularly preferably 120°C or less and very particularly preferably 100°C or less.

[0361] The nematic phase of the media according to the invention preferably extends from at least below 0° C. to above 90° C. The media according to the invention advantageously exhibit an even wider nematic phase range, preferably from at least below −10° C. to above 120° C., very preferably from at least below 20° C. to above 140° C., particularly preferably from at least below 30° C. to above 150° C., and very particularly preferably from at least below 40° C. to above 170° C.

[0362] The Δε at 1 kHz and 20° C. of the liquid-crystalline media according to the invention is preferably 1 or more, more preferably 2 or more, very preferably 3 or more.

[0363] 589 nm (Na D ) and birefringence (Δn) at 20° C. is preferably 0.280 or more, more preferably 0.300 or more, even more preferably 0.320 or more, very preferably 0.330 or more, and especially 0.350 or more.

[0364] 589 nm (Na D ) and Δn at 20° C. is preferably in the range of 0.200 to 0.900, more preferably in the range of 0.250 to 0.800, even more preferably in the range of 0.300 to 0.700, and very particularly preferably in the range of 0.350 to 0.600.

[0365] In a preferred embodiment of the present invention, the Δn of the liquid-crystalline media according to the present invention is preferably ≧0.50, more preferably ≧0.55.

[0366] The compounds of formulas I to III in each case include dielectrically positive compounds having a dielectric anisotropy greater than 3, dielectrically neutral compounds having a dielectric anisotropy less than 3 and greater than -1.5, and dielectrically negative compounds having a dielectric anisotropy of -1.5 or less.

[0367] The compounds of formulae U, I, II and III are preferably dielectrically positive.

[0368] V0 represents the capacitive threshold voltage [V] at 20°C in the antiparallel rubbed cell, n e represents the extraordinary refractive index at 20°C and 589 nm, n0 represents the ordinary refractive index at 20°C and 589 nm; Δn represents the optical anisotropy at 20°C and 589 nm; ε ⊥ represents the dielectric constant perpendicular to the director at 20°C and 1 kHz, ε ∥ represents the dielectric constant parallel to the director at 20°C and 1 kHz, Δε is the dielectric anisotropy (Δε = ε) at 20°C and 1 kHz. ∥ -ε ⊥ ) and T(N,I) is the clearing point [°C], i.e., the transition from the nematic to the isotropic phase, γ1 represents the rotational viscosity [mPa·s] measured at 20°C, K1 represents the elastic constant for "splay" deformation at 20°C [pN], K2 represents the elastic constant [pN] for "twist" deformation at 20°C, K3 represents the elastic constant [pN] for "bend" deformation at 20°C.

[0369] In this application, dielectrically positive refers to compounds with Δε > 3.0, dielectrically neutral refers to those with -1.5 ≤ Δε ≤ 3.0, and dielectrically negative refers to those with Δε < -1.5. Δε is determined at a frequency of 1 kHz and 20°C. The dielectric anisotropy of each compound is determined from a 10% solution of each individual compound in a nematic host mixture. If the solubility of each compound in the host mixture is less than 10%, the concentration is reduced to 5%. The capacitance of the test mixtures is determined in both cells with homeotropic alignment and cells with homogeneous alignment. The cell thickness of both types of cells is approximately 20 μm. The applied voltage is a square wave with a frequency of 1 kHz and an effective value typically between 0.5 V and 1.0 V, which is always selected to be below the capacitance threshold of each test mixture.

[0370] Δε is (ε ∥ -ε ⊥ ), while ε ave is (ε ∥ +2ε ⊥ ) / 3.

[0371] The host mixture used to determine the physical constants of the pure compounds by extrapolation is ZLI-4792 from Merck, Germany. The absolute values ​​of the dielectric constant, birefringence (Δn), and rotational viscosity (γ1) of the compound are determined from the change in the respective values ​​of the host mixture upon addition of the compound. The concentration in the host is 10% or 5% if solubility is insufficient. The values ​​are extrapolated to 100% for the added compound.

[0372] In the examples the phase sequences of the pure compounds are given using the following abbreviations: K: crystalline, N: nematic, SmA: smectic A, SmB: smectic B, I: isotropic.

[0373] Components that have a nematic phase at a measurement temperature of 20°C are measured as they are, and other components are treated in the same manner as compounds.

[0374] In any case, unless otherwise specified, the term "threshold voltage" in this application refers to the optical threshold voltage at which 10% relative contrast (V 10 ) and the expression "saturation voltage" refers to optical saturation and 90% relative contrast (V 90 ) is quoted. The capacitance threshold voltage (V0) is the Fredericks threshold (V Fr ) and should only be used when explicitly stated.

[0375] All parameter ranges given herein are inclusive unless otherwise stated.

[0376] The different upper and lower limits set forth for the various range properties may be combined with each other to create additional preferred ranges.

[0377] Throughout this application, the following conditions and definitions apply unless stated otherwise: All concentrations are quoted in weight percent, all temperatures are quoted in degrees Celsius, and all temperature differences are quoted in degrees Celsius, with respect to the respective mixture total. All physical properties are determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals," November 1997, Merck, Germany, and are quoted for a temperature of 20°C unless stated otherwise. The optical anisotropy (Δn) is determined at a wavelength of 589.3 nm. The dielectric anisotropy (Δε) is determined at a frequency of 1 kHz. The threshold voltage as well as all other electro-optical properties are determined using test cells manufactured by Merck. The test cells for determining Δε have a cell thickness of approximately 20 μm. The electrodes are 1.13 cm thick. 2The ITO electrode is a circular electrode with an area of ​​100 μm and a guard ring. The alignment layer provides homeotropic alignment (ε ∥ ) is SE-1211 manufactured by Nissan Chemical Co., Ltd. in Japan, and homogeneous orientation (ε ⊥ ) is polyimide AL-1054 manufactured by Japan Synthetic Rubber Co., Ltd. The capacitance is 0.3V rms The characteristic voltage is determined using a Solatron 1260 frequency response analyzer using a sine wave with a voltage of 1000 Hz. The light used for the electro-optical measurements is white light. In this specification, an instrument configuration using a DMS device commercially available from Autronic-Melchers, Germany, is used. The characteristic voltage was determined under normal observation. The threshold voltage (V 10 ), medium gray (V 50 ) and saturation (V 90 ) voltages were determined at 10%, 50% and 90% relative contrast, respectively.

[0378] Liquid-crystalline media are investigated with regard to their properties in the microwave frequency range as described in A. Penirschke et al., "Cavity Perturbation Method for Characterization of Liquid Crystals up to 35 GHz", 34th European Microwave Conference - Amsterdam, pp. 545-548. Comparison is also made to A. Gaebler et al., "Direct Simulation of Material Permittivites (omitted)", 12MTC2009 - International Instrumentation and Measurement Technology Conference, Singapore, 2009 (IEEE), pp. 463-467 and DE 10 2004 029 429 A1, in which the measurement method is likewise described in detail.

[0379] The liquid crystal is introduced into a cylindrical polytetrafluoroethylene (PTFE) or quartz capillary. The capillary has an inner diameter of 180 μm and an outer diameter of 350 μm. The effective length is 2.0 cm. The filled capillary is introduced into the center of a cylindrical cavity with a resonant frequency of 19 GHz. The cavity has a length of 11.5 mm and a radius of 6 mm. An input signal (signal source) is then applied, and the resulting output signal is recorded using a commercially available vector network analyzer (N5227A PNA Microwave Network Analyzer, Keysight Technologies, USA). For other frequencies, the cavity dimensions are adapted accordingly.

[0380] The change in resonant frequency and the Q factor between measurements with and without the capillary filled with liquid crystal are used to determine the dielectric constant and loss angle at the corresponding target frequency using equations 10 and 11 as described in the above-mentioned publication by A. Penirschke et al., "Cavity Perturbation Method for Characterisation of Liquid Crystals up to 35 GHz", 34th European Microwave Conference - Amsterdam, pp. 545-548.

[0381] The values ​​of the characteristic components perpendicular and parallel to the director of the liquid crystal are obtained by orienting the liquid crystal in a magnetic field. For this purpose, a permanent magnet's field strength of 0.35 Tesla is used.

[0382] Preferred components are phase shifters, varactors, radio and radio frequency antenna arrays, matching circuits adaptive filters and others.

[0383] In this application, the term "compound" is intended to mean both one compound and multiple compounds, unless otherwise specified.

[0384] All mixtures according to the invention are nematic. The liquid-crystalline media according to the invention preferably have a nematic phase within the preferred ranges given above. Having a nematic phase here means, on the one hand, that no smectic phase or crystallization is observed at the corresponding temperature, and, on the other hand, that no clearing occurs upon heating from the nematic phase. At high temperatures, the clearing point is measured in capillaries using conventional methods. Low-temperature studies are carried out at the corresponding temperature using a flow viscometer and confirmed by storage of bulk samples. The bulk storage stability (LTS) of the media according to the invention at a given temperature T is determined by visual inspection. 2 g of the medium to be studied is filled into a sealed glass container (bottle) of appropriate size, placed in a refrigerator at the specified temperature. The bottles are checked at defined time intervals for the appearance of smectic phases or crystallization. Two bottles are stored for each material and at each temperature. If crystallization or the appearance of a smectic phase is observed in at least one of the two corresponding bottles, the test is terminated, and the last inspection time before the appearance of a higher-order phase is recorded as the respective storage stability. Finally, the test is terminated after 1000 hours, i.e., an LTS value of 1000 hours means that the mixture is stable at a given temperature for at least 1000 hours.

[0385] The liquid crystals employed preferably have a positive dielectric anisotropy, which is preferably 2 or more, preferably 4 or more, particularly preferably 6 or more, very particularly preferably 10 or more.

[0386] The liquid-crystalline media according to the invention are furthermore characterised by high anisotropy values ​​in the microwave range. The birefringence at about 19 GHz is, for example, preferably 0.14 or more, particularly preferably 0.15 or more, particularly preferably 0.20 or more, particularly preferably 0.25 or more, very particularly preferably 0.30 or more. In addition, the birefringence is preferably 0.80 or less.

[0387] The dielectric anisotropy in the microwave region is defined as follows:

[0388]

number

[0389] Tunability (τ) is defined as follows:

[0390]

number

[0391] The material quality (η) is defined as follows:

[0392]

number

[0393] where the maximum dielectric loss is below.

[0394]

number

[0395] The tunability τ of the media according to the invention measured at 20° C. and 19 GHz is 0.250 or greater, preferably 0.300 or greater, 0.310 or greater, 0.320 or greater, 0.330 or greater or 0.340 or greater, very preferably 0.345 or greater, in particular 0.350 or greater.

[0396] Preferred liquid crystal materials have a material quality (η) of 6 or more, preferably 8 or more, preferably 10 or more, preferably 15 or more, preferably 17 or more, preferably 20 or more, particularly preferably 25 or more, very particularly preferably 30 or more.

[0397] Preferred liquid crystal materials in the corresponding components have a phase shift of 15° / dB or more, preferably 20° / dB or more, preferably 30° / dB or more, preferably 40° / dB or more, preferably 50° / dB or more, particularly preferably 80° / dB or more, very particularly preferably 100° / dB or more.

[0398] However, in some embodiments, liquid crystals with negative values ​​of dielectric anisotropy can also be used.

[0399] The liquid crystals used are either individual substances or mixtures. They preferably have a nematic phase.

[0400] The liquid-crystalline media according to the invention may contain further additives and chiral dopants in the usual concentrations. The total concentration of these further components 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 in the range of 0.1% to 3%. The concentrations of these and similar additives are not taken into account when citing the values ​​and concentration ranges of the liquid-crystalline compounds of the liquid-crystalline media in this application.

[0401] Preferably, the media according to the invention comprise one or more chiral compounds as chiral dopants to adjust their cholesteric pitch, the total concentration of which in the media according to the invention is preferably in the range of 0.05% to 15%, more preferably 1% to 10%, most preferably 2% to 6%.

[0402] Optionally, the media according to the invention contain further liquid crystal compounds to adjust the physical properties. Such compounds are known to the expert. Their concentration in the media according to the invention is preferably 0% to 30%, more preferably 0.1% to 20%, most preferably 1% to 15%.

[0403] The response time is the time (t 90 -t0), that is, the delay time (t 10 -t0) including the rise time (τ on ) and the time (t) for the relative tuning of the electro-optic response to change from 100% back to 10%, respectively. 100 -t 10 ) versus decay time (τ off ) and the total response time (τ total =τ on +τoff ) are shown respectively.

[0404] The liquid-crystalline media according to the present invention comprise a plurality of compounds, preferably 3 to 30, more preferably 4 to 20, and very preferably 4 to 16 compounds. These compounds are mixed in the usual manner. In general, the desired amount of the compound used in a smaller amount is dissolved in the compound used in a larger amount. It is particularly easy to observe the completion of the dissolution process when the temperature is higher than the clearing point of the compound used in a higher concentration. However, it is also possible to prepare the media using other conventional methods, such as so-called premixes, whose components are ready-to-use mixtures, for example, homogeneous mixtures or eutectic mixtures of compounds, or, for example, using so-called "multi-bottle" systems.

[0405] All temperatures are quoted in degrees Celsius, e.g., melting points T(C,N) or T(C,S), smectic (S) to nematic (N) phase transitions T(S,N), and liquid crystal clearing points T(N,I). All temperature differences are quoted in degrees Celsius.

[0406] In the present invention and in particular in the following examples, the structures of the mesogenic compounds are represented by abbreviations, also called acronyms. These acronyms are used in tables A to D below to abbreviate the chemical formulae as follows: n H 2n+1 , C m H 2m+1 and C l H 2l+1 or C n H2 n-1 , C m H 2m-1 and C l H 2-1 represents a straight-chain alkyl or alkenyl, preferably 1E-alkenyl, having n, m and 1 C atoms, respectively. Table A lists the codes used for the ring elements of the core structure of the compounds, while Table B shows the linking groups. Table C gives the meaning of the codes for the left- or right-hand terminal groups. Table D shows exemplary structures of compounds, along with their respective abbreviations.

[0407] <Table A: Ring elements>

[0408] [Table 1]

[0409] [Table 2]

[0410] [Table 3]

[0411] [Table 4]

[0412] [Table 5]

[0413] <Table B: Linking group>

[0414] [Table 6]

[0415] <Table B: Terminal group>

[0416] [Table 7]

[0417] In the table, n and m each represent an integer, and the three dots "..." are places for other abbreviations from this table.

[0418] Branched side groups are numbered starting from the position next to the ring with the longest chain selected (1), with lower numbers indicating the length of the branch and the subscript numbers in parentheses indicating the position of the branch. For example:

[0419] [ka]

[0420] [ka]

[0421] The following table shows exemplary structures with their respective abbreviations, which are provided to illustrate the meaning of the abbreviation rules, which further represent preferred compounds.

[0422] Table C: Exemplary Structures The following exemplary structures are compounds that are preferably additionally used in the medium.

[0423] [Table 8]

[0424] [Table 9]

[0425] [Table 10]

[0426] [Table 11]

[0427] [Table 12]

[0428] [Table 13]

[0429] [Table 14]

[0430] [Table 15]

[0431] [Table 16]

[0432] [Table 17]

[0433] [Table 18]

[0434] [Table 19]

[0435] [Table 20]

[0436] [Table 21]

[0437] In the table, m and n are the same or different and are 1, 2, 3, 4, 5, 6, or 7.

[0438] Preferably, the medium according to the invention comprises one or more compounds selected from the compounds of Table C.

[0439] The following table, Table D, shows exemplary compounds that can be used as alternative stabilizers in mesogenic media according to the invention. The total concentration of these and similar compounds in the media is preferably 5% or less.

[0440]

[0441] [Table 22]

[0442] [Table 23]

[0443] In a preferred embodiment of the present invention the mesogenic medium comprises one or more compounds selected from the group of compounds from Table D.

[0444] The following table, Table E, shows exemplary compounds which can be preferably used as chiral dopants in the mesogenic media according to the present invention.

[0445]

[0446] [Table 24]

[0447] [Table 25]

[0448] [Table 26]

[0449] In a preferred embodiment of the invention the mesogenic medium comprises one or more compounds selected from the group of compounds in Table E.

[0450] The mesogenic medium according to the present application preferably comprises two or more, preferably four or more compounds selected from the group consisting of the compounds in the table above. [Example]

[0451] The following examples illustrate the present invention without limiting it in any way. From the physical properties, it is clear to those skilled in the art what properties can be achieved and to what extent they can be varied. Therefore, the combinations of various properties that can be particularly preferably achieved are well defined for those skilled in the art.

[0452] <Synthesis example>

[0453] Abbreviation RT Room temperature (typically 20°C above or below 1°C) THF tetrahydrofuran MTB Methyl tert-butyl ether DCM dichloromethane dist. distillation

[0454] <Example 1> 1,2,4,5-tetrafluoro-3-isothiocyanate-6-[4-(4-propylcyclohexyl)phenyl]benzene

[0455] <Step 1.1> 2,3,5,6-tetrafluoro-4-[4-(4-propylcyclohexyl)phenyl]aniline

[0456] [ka]

[0457] A solution of [4-(4-propylcyclohexyl)phenyl]boronic acid (CAS No. 156837-90-0, 5.3 g, 22 mmol) and 4-bromo-2,3,5,6-tetrafluoroaniline (CAS No. 1998-66-9, 5.0 g, 21 mmol) in THF (30 mL) was heated to 50 °C, and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.87 mg) was added. The mixture was heated to reflux, and then aqueous sodium hydroxide (2 M, 15.4 mL, 31 mmol) was added dropwise. The reaction mixture was stirred at reflux for 2 hours, after which a solution of [4-(4-propylcyclohexyl)phenyl]boronic acid (1.0 g, 4 mmol) in THF (15 mL) was added dropwise, and the mixture was stirred at reflux overnight. The mixture is then cooled to room temperature, treated with acetic acid (1.6 mL glacial acetic acid), and diluted with MTB ether. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane and MTB ether) to give 2,3,5,6-tetrafluoro-4-[4-(4-propylcyclohexyl)phenyl]aniline as a pale yellow solid.

[0458] <Step 1.2> 1,2,4,5-tetrafluoro-3-isothiocyanate-6-[4-(4-propylcyclohexyl)phenyl]benzene

[0459] [ka]

[0460] A solution of 2,3,5,6-tetrafluoro-4-[4-(4-propylcyclohexyl)phenyl]aniline (7.4 g, 20 mmol) and 1,4-diazabicyclo[2.2.2]octane (5.7 g, 51 mmol) in DCM (100 mL) is cooled to 0 °C, and thiophosgene (1.8 mL, 22 mmol) is added dropwise. The reaction mixture is stirred at room temperature for 60 min. The reaction mixture is then hydrolyzed with distilled water and brine and diluted with DCM. The aqueous phase is separated and extracted with DCM. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane) and crystallization (n-heptane). 1,2,4,5-tetrafluoro-3-isothiocyanato-6-[4-(4-propylcyclohexyl)phenyl]benzene is isolated as a colorless solid.

[0461] [Table 27]

[0462] <Example 2> 1,2,4,5-tetrafluoro-3-isothiocyanate-6-[4-[4-(trifluoromethoxy)phenyl]phenyl]benzene

[0463] <Step 2.1> 4,4,5,5-tetramethyl-2-[4-[4-(trifluoromethoxy)phenyl]phenyl]-1,3,2-dioxaborolane

[0464] [ka]

[0465] Bis(pinacolato)diboron (14.3 g, 56 mmol) and potassium acetate (14.3 g, 146 mmol) are added to a solution of 1-bromo-4-[4-(trifluoromethoxy)phenyl]benzene (CAS No. 134150-03-1, 16.9 g, 49 mmol) in 1,4-dioxane (150 mL). This mixture is then treated with 1,1'-bis(biphenylphosphine)ferrocenepalladium dichloride (1.2 g, 1.6 mmol) and stirred at reflux overnight. The reaction mixture is cooled to room temperature, hydrolyzed with distilled water, diluted with MTB ether, and filtered over Celite. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane and 1-chlorobutane) to give 4,4,5,5-tetramethyl-2-[4-[4-(trifluoromethoxy)phenyl]phenyl]-1,3,2-dioxaborolane as a brown solid.

[0466] <Step 2.2> 2,3,5,6-tetrafluoro-4-[4-[4-(trifluoromethoxy)phenyl]phenyl]aniline

[0467] [ka]

[0468] A solution of 4,4,5,5-tetramethyl-2-[4-[4-(trifluoromethoxy)phenyl]phenyl]-1,3,2-dioxaborolane (3.0 g, 7.4 mmol) and 4-bromo-2,3,5,6-tetrafluoroaniline (1.6 g, 6.6 mmol) in THF (11 mL) is treated with bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.31 mg) at 50 °C. The mixture is then heated to reflux, and sodium hydroxide solution (2.0 M, 5.5 mL) is added dropwise. The reaction mixture is stirred at reflux overnight. It is then cooled to ambient temperature, treated with acetic acid (glacial, 0.6 mL), and diluted with MTB ether. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane and 1-chlorobutane). 2,3,5,6-tetrafluoro-4-[4-[4-(trifluoromethoxy)phenyl]phenyl]aniline is isolated as a light brown solid.

[0469] <Step 2.3> 1,2,4,5-tetrafluoro-3-isothiocyanate-6-[4-[4-(trifluoromethoxy)phenyl]phenyl]benzene

[0470] [ka]

[0471] A solution of 2,3,5,6-tetrafluoro-4-[4-[4-(trifluoromethoxy)phenyl]phenyl]aniline (2.0 g, 4.9 mmol) and 1,4-diazabicyclo[2.2.2]octane (1.4 g, 12.2 mmol) in DCM (25 mL) is cooled to 0 °C and treated dropwise with thiophosgene (0.4 mL, 5.4 mmol). The reaction mixture is stirred at room temperature for 60 min. It is then hydrolyzed with distilled water and brine and diluted with DCM. The aqueous phase is separated and extracted with DCM. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane and 1-chlorobutane) and crystallization (n-heptane) to give 1,2,4,5-tetrafluoro-3-isothiocyanato-6-[4-[4-(trifluoromethoxy)phenyl]phenyl]benzene as a colorless solid.

[0472] [Table 28]

[0473] <Example 3> 1-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,3,5,6-tetrafluoro-4-isothiocyanate benzene

[0474] <Step 3.1> 2-[4-[2-(4-butylphenyl)ethynyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0475] [ka]

[0476] A solution of 1-butyl-4-ethynyl-benzene (CAS number 79887-09-5, 1.2 g, 7.1 mmol), 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS number 68716-49-4, 2.0 g, 7.1 mmol) and diisopropylamine (17 mL) in THF (20 mL) is heated just below reflux. Copper(I) iodide (1.4 mg), 2-dicyclohexylphosphino-2'4'6'-triisopropyl-1,1'-biphenyl (6.7 mg), and chloro(2-dicyclohexylphosphino-2'4'6'-triisopropyl-1,1'-biphenyl),(2'-amino-1,1'-biphenyl-2-yl)palladium(II) (11.1 mg) were added, and the reaction mixture was stirred at reflux overnight. It was then cooled to room temperature, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (n-heptane and 1-chlorobutane) to give 2-[4-[2-(4-butylphenyl)ethynyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a brown oil, which crystallized on standing.

[0477] <Step 3.2> 4-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,3,5,6-tetrafluoroaniline

[0478] [ka]

[0479] A solution of 2-[4-[2-(4-butylphenyl)ethynyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.8 g, 4.7 mmol) and 4-bromo-2,3,5,6-tetrafluoroaniline (1.8 g, 2.0 mmol) in THF (10 mL) is treated with bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.2 g) at 50 °C. The reaction mixture is then heated to reflux, and then aqueous sodium hydroxide (2.0 M, 3.6 mL) is added dropwise, and the reaction is allowed to stir at reflux overnight. The reaction mixture is then cooled to room temperature, treated with acetic acid (glacial, 0.4 mL), and diluted with MTB ether. The aqueous phase is separated and extracted with MTB ether. The combined organic phase is washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane and 1-chlorobutane) to give 4-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,3,5,6-tetrafluoroaniline as a pale yellow solid.

[0480] <Step 3.3> 1-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,3,5,6-tetrafluoro-4-isothiocyanatebenzene

[0481] [ka]

[0482] A solution of 4-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,3,5,6-tetrafluoroaniline (3.0 g, 6.8 mmol) and 1,4-diazabicyclo[2.2.2]octane (1.9 g, 7.4 mmol) in DCM (35 mL) is treated dropwise with thiophosgene (0.6 mL, 7.4 mmol) at 0 °C. The reaction mixture is then stirred at room temperature for 60 minutes. It is hydrolyzed with distilled water and brine and diluted with DCM. The aqueous phase is separated and extracted with DCM. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane and MTB ether) and crystallization (acetone) to give 1-[4-[2-(4-butylphenyl)ethynyl]phenyl]-2,3,5,6-tetrafluoro-4-isothiocyanatobenzene as a colorless solid.

[0483] [Table 29]

[0484] <Example 4> 1,2,4,5-tetrafluoro-3-isothiocyanate-6-[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]benzene

[0485] <Step 4.1> 4,4,5,5-tetramethyl-2-[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]-1,3,2-dioxaborolane

[0486] [ka]

[0487] A solution of 1-ethynyl-4-(trifluoromethoxy)benzene (CAS No. 160542-02-9, 3.0 g, 15 mmol), 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.3 g, 15 mmol), and diisopropylamine (37 mL) in THF (40 mL) was heated slightly below reflux. Copper(I) iodide (2.9 mg), 2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (14.6 mg), and chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl),(2'-amino-1,1'-biphenyl-2-yl)palladium(II) (24 mg) were added, and the reaction mixture was stirred at reflux overnight. It is then cooled to room temperature, filtered, and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent: n-heptane and DCM) to give 4,4,5,5-tetramethyl-2-[4-[2-[4-(trifluoromethoxy)phenyl]-ethynyl]phenyl]-1,3,2-dioxaborolane as a brown oil, which crystallizes on standing.

[0488] <Step 4.2> 2,3,5,6-tetrafluoro-4-[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]aniline

[0489] [ka]

[0490] A solution of 4,4,5,5-tetramethyl-2-[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]-1,3,2-dioxaborolane (5.8 g, 12 mmol) and 4-bromo-2,3,5,6-tetrafluoroaniline (2.9 g, 12 mmol) in THF (18 mL) is treated with bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.5 mg) at 50 ° C. The reaction mixture is then heated to reflux, and then aqueous sodium hydroxide (2.0 M, 9.3 mL) is added dropwise. It is stirred at reflux overnight. The reaction mixture is then cooled to room temperature, treated with acetic acid (glacial, 1.1 mL), and diluted with MTB ether. The aqueous phase is separated and extracted with MTB ether. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (solvent n-heptane and 1-chlorobutane) to give 2,3,5,6-tetrafluoro-4-[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]aniline as a pale yellow solid.

[0491] <Step 4.3> 1,2,4,5-tetrafluoro-3-isothiocyanato-6-[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]benzene

[0492] [ka]

[0493] A solution of 2,3,5,6-tetrafluoro-4-[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]aniline (4.7 g, 8 mmol) and 1,4-diazabicyclo[2.2.2]octane (2.2 g, 19 mmol) in DCM (30 mL) is treated dropwise with thiophosgene at 0 °C. The reaction mixture is stirred at room temperature for 60 minutes. It is then hydrolyzed with distilled water and brine and diluted with DCM. The aqueous phase is separated and extracted with DCM. The combined organic phases are washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue is purified by silica gel chromatography (n-heptane and 1-chlorobutane) and crystallization (n-heptane and acetone). 1,2,4,5-tetrafluoro-3-isothiocyanato-6-[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]benzene is obtained as a colorless solid.

[0494] [Table 30]

[0495] The following compounds are obtained in a similar manner to Synthesis Examples 1 to 4.

[0496] [Table 31]

[0497] [Table 32]

[0498] [Table 33]

[0499] [Table 34]

[0500] [Table 35]

[0501] [Table 36]

[0502] [Table 37]

[0503] <Mixture example> Liquid crystal mixtures N1 to N13 having the compositions and properties shown in the table below are prepared and characterized with respect to their general physical properties and applicability in microwave components at 19 GHz and 20°C.

[0504] <Comparison mixture C1>

[0505] [Table 38]

[0506] <Comparative mixture C2>

[0507] [Table 39]

[0508] <Example N1>

[0509] [Table 40]

[0510] Example N1 corresponds to comparative mixture C1 in which compound PGU-3-S is replaced by compound CPU(F,F)-3-S according to the invention. Surprisingly, this has the effect of improving (lowering) the dielectric losses, resulting in an improvement in material quality (η) from η = 32.0 to 35.4.

[0511] <Example N2>

[0512] [Table 41]

[0513] Example N2 corresponds to comparative mixture C1 in which compound CPU-2-S is replaced by compound CPU(F,F)-3-S according to the invention, which surprisingly has the effect of improving (lowering) the dielectric losses, resulting in an improvement in the figure of merit η from 38.4 to 41.3.

[0514] <Example N3>

[0515] [Table 42]

[0516] <Example N4>

[0517] [Table 43]

[0518] <Example N5>

[0519] [Table 44]

[0520] <Example N6>

[0521] [Table 45]

[0522] <Example N7>

[0523] [Table 46]

[0524] <Example N8>

[0525] Table 47

[0526] <Example N9>

[0527] Table 48

[0528] <Example N10>

[0529] Table 49

[0530] <Example N11>

[0531]

Table 50

[0532] <Example N12>

[0533] Table 51

[0534] <Example N13>

[0535] Table 52

[0536] <Example N14>

[0537] Table 53

[0538] <Example N15>

[0539] Table 54

[0540] <Example N16>

[0541] Table 55

[0542] <Example N17>

[0543] Table 56

[0544] <Example N18>

[0545] Table 57

[0546] <Example N19>

[0547] Table 58

[0548] <Example N20>

[0549] Table 59

[0550] <Example N21>

[0551] Table 60

[0552] <Example N22>

[0553] Table 61

[0554] <Example N23>

[0555] Table 62

[0556] <Example N24>

[0557] Table 63

[0558] <Example N25>

[0559] Table 64

[0560] <Example N26>

[0561] Table 65

[0562] <Example N27>

[0563] Table 66

[0564] <Example N28>

[0565] Table 67

[0566] <Example N29>

[0567] Table 68

[0568] <Example N30>

[0569] Table 69

[0570] <Example N31>

[0571] Table 70

[0572] <Example N32>

[0573] Table 71

[0574] <Example N34>

[0575] Table 72

[0576] <Example N35>

[0577] Table 73

[0578] <Example N36>

[0579] Table 74

[0580] <Example N37>

[0581] Table 75

[0582] <Example N38>

[0583] Table 76

[0584] <Example N39>

[0585] Table 77

[0586] <Example N40>

[0587] Table 78

[0588] <Example N41>

[0589] Table 79

[0590] <Example N42>

[0591] Table 80

[0592] <Example N43>

[0593] Table 81

[0594] <Example N44>

[0595] [Table 82]

[0596] <Example N45>

[0597] [Table 83]

[0598] <Example N46>

[0599] [Table 84]

[0600] <Example N46>

[0601] [Table 85]

[0602] The liquid-crystalline media according to the invention exhibit a high clearing temperature in combination with very good LTS and excellent properties relevant for microwave applications. Compared to media known from the prior art, a higher material quality (η) is observed due to a higher tunability (τ) and / or a lower dielectric loss (tan δ).

Claims

1. A compound of formula U. 【Chemical 1】 (In the formula, R Ｕ represents straight-chain or branched alkyl having 1 to 12 C atoms or cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl or cyclopentenylalkyl having 3 to 12 C atoms, Z Ｕ１ , Z Ｕ２ represents a single bond, X １ , X ２ , X ３ and X ４ represents F, t is 1, 【Chemistry 2】 represents 【Chemistry 3】 represents L 1 represents H, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopentenyl.

2. A compound selected from compounds 1 and 21-27. 【Chemistry 4】 【Chemistry 5】

3. A compound of the acronym CPU(F,F)-n-S. 【Chemistry 6】 (In the formula, n is 1, 2, 3, 4, 5, 6 or 7.

4. A compound of the acronym CPU(F,F)-(c3)n-S. 【Chemistry 7】 (In the formula, n is 0, 1, 2, 3, 4, 5, 6 or 7.

5. Liquid-crystalline medium comprising one or more compounds according to any one of claims 1 to 4.

6. The liquid crystal medium of claim 5, further comprising one or more compounds selected from the group of compounds of formulae I, II and III. 【Chemistry 8】 (In the formula, R １ represents H, a non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17 C atoms, or a non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH ２ The base is 【Chemistry 9】 may be replaced by n is 0, 1 or 2; 【Chemistry 10】 represents In the formula, R Ｌ are identical or different at each occurrence and represent H or alkyl having 1 to 6 C atoms, and, however, or 【Chemistry 11】 represents R ２ represents H, a non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17 C atoms, or a non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH ２ The base is 【Chemistry 12】 may be replaced by Z ２１ represents trans-CH=CH-, trans-CF=CF- or -C≡C-, and 【Chemistry 13】 represents In the formula, R Ｌ are identical or different at each occurrence and represent H or alkyl having 1 to 6 C atoms, R ３ represents H, a non-fluorinated alkyl or non-fluorinated alkoxy having 1 to 17 C atoms, or a non-fluorinated alkenyl, non-fluorinated alkenyloxy or non-fluorinated alkoxyalkyl having 2 to 15 C atoms, in which one or more CH ２ The base is 【Chemistry 14】 may be replaced by Z ３１ and Z ３２ one of represents trans-CH=CH-, trans-CF=CF-, or -C≡C-, and the other independently represents -C≡C-, trans-CH=CH-, trans-CF=CF-, or a single bond; and 【Chemistry 15】 represents In the formula, R Ｌ are identical or different at each occurrence and represent H or alkyl having 1 to 6 C atoms, and, however, or 【Chemistry 16】 Represents.)

7. 7. The liquid-crystalline medium according to claim 6, comprising one or more compounds selected from the group of compounds of the formulae I-1 to I-5 【Chemistry 17】 (In the formula, L １ , L ２ and L ３ are the same or different and represent H or F at each occurrence, and R １ 、 【Chemistry 18】 has the meaning given to formula I in claim 6.

8. 8. The liquid-crystalline medium according to claim 6, comprising one or more compounds selected from the group of compounds of the formulae II-1 to II-3 【Chemistry 19】 (In the formula, R ２ 、 【Chemistry 20】 has the meaning given to formula II in claim 6.

9. 9. The liquid-crystalline medium according to claim 6, comprising one or more compounds selected from the group of compounds of the formulae III-1 to III-6 【Chemical 21】 (In the formula, R ３ 、 【Chemical 22】 has the meaning given to formula III in claim 6, and Z ３１ and Z ３２ are each independently trans-CH=CH- or trans-CF=CF-, or in formula III-6, Z ３１ and Z ３２ may represent -C≡C-.

10. 10. The liquid-crystalline medium according to claim 6, which comprises one or more compounds selected from the group consisting of the following compounds: 【Chemical 23】 【Chemistry 24】 (In the formula, m and n are the same or different and each represents 1, 2, 3, 4, 5, 6, or 7.

11. Components for high frequency technology, characterized in that they contain a liquid-crystalline medium according to any one of claims 5 to 10.

12. 12. The component of claim 11, which is a liquid crystal based antenna element, a phase shifter, a tunable filter, a tunable material structure, a matching network or a varactor.

13. A microwave antenna array, characterized in that it comprises one or more components according to claim 11 or 12.

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