heteroaromatic isothiocyanates

Abstract

The present invention relates to heteroaromatic isothiocyanates of the formula N as defined in claim 1, to liquid-crystalline media comprising one or more compounds of the formula N, and to high-frequency components, in particular microwave components, comprising these media, especially for high-frequency devices, such as devices that shift microwaves, tunable filters, tunable metamaterial structures, and electronic beam steering antennas, for example phased array antennas.

Description

[0001] This invention relates to heteroaromatic isothiocyanates, liquid crystal media comprising them, and high-frequency components comprising these media, particularly microwave components for high-frequency devices such as microwave phase-shifting devices, tunable filters, tunable metamaterial structures, and electronic beam-steering antennas (e.g., phase array antennas), as well as devices comprising said components.

[0002] Liquid crystal media have been used for many years in electro-optical displays (LCDs) to display information. However, recently, liquid crystal media have also been proposed for use in components of microwave technology, such as in DE 10 2004 029 429.1A and JP 2005-120208(A).

[0003] A. Gaebler, F. Goelden, S. Müller, 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, describe the corresponding properties of the known liquid crystal mixture E7 (Merck KGaA, Germany).

[0004] DE 10 2004 029 429 A describes the use of liquid crystal media in microwave technology, particularly in phase shifters. The characteristics of the liquid crystal media in the relevant frequency range are discussed, and liquid crystal media based primarily on mixtures of aromatic nitriles and isothiocyanates are shown.

[0005] In EP 2 982 730 A1, a mixture consisting entirely of isothiocyanate compounds is described.

[0006] Fluorine atoms are commonly used in mesocrystalline compounds to introduce polarity. In particular, combinations with terminal NCS groups with high dielectric anisotropy values ​​can be achieved.

[0007] However, compositions suitable for microwave applications still have several drawbacks. Improvements are needed in the general physical properties, shelf life, and stability during operation in devices. Given the numerous parameters that must be considered and modified for developing liquid crystal media for microwave applications, a wider range of possible mixtures for developing such liquid crystal media is desirable.

[0008] One object of the present invention is to provide a compound for a liquid crystal medium having improved properties related to applications in the microwave range of the electromagnetic spectrum.

[0009] To address this problem, a compound of formula N shown below and a liquid crystal medium containing the compound are provided.

[0010] Therefore, this invention relates to compounds of formula N.

[0011]

[0012] in

[0013] R N The expression represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenyloxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2 groups may be derived from H. Substitution, or indicating group R P ,

[0014] R P Indicates halogen, CN, NCS, R F R F -O- or R F -S-, where

[0015] R F This indicates a fluorinated alkyl group having 1 to 9 carbon atoms or a fluorinated alkenyl group having 2 to 9 carbon atoms.

[0016] Z N1 and Z N2 Same or different indicates -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, or a single bond.

[0017] X represents CH, N, CF, or C-Cl.

[0018] Y 1 and Y 2 Same or different, indicating H, Cl, F, methyl or ethyl,

[0019] and

[0020] Groups selected from the following groups:

[0021] a) The group consisting of 1,4-phenylene, 1,4-naphthylene, and 2,6-naphthylene, wherein one or two CH groups may be substituted with N and one or more H atoms may be substituted with L.

[0022] b) The group consisting of trans-1,4-cyclohexene, 1,4-cyclohexenyl, bicyclo[1.1.1]pentane-1,3-diyl, 4,4′-dicyclohexene, bicyclo[2.2.2]octane-1,4-diyl and spiro[3.3]heptane-2,6-diyl, wherein one or more non-adjacent CH2 groups may be substituted with -O- and / or -S- and one or more H atoms may be substituted with F.

[0023] c) The group consisting of thiophene-2,5-diyl, thiophene[3,2-b]thiophene-2,5-diyl, and selenophene-2,5-diyl, each of which may also be L-mono- or poly-substituted.

[0024] L may be the same or different each time it appears, representing F, Cl, CN, SCN, SF5, or a straight or branched chain, and in each case, optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy groups having 1 to 12 carbon atoms.

[0025] t can be 0, 1, or 2.

[0026] This invention further relates to compounds of formula NH

[0027]

[0028] The groups and parameters mentioned herein have the meanings given above for formula N and relate to a method for synthesizing a compound of formula N from a compound of formula NH.

[0029] The present invention further relates to liquid crystal media containing N-type compounds and to the use of a liquid crystal medium containing N-type compounds in components for high-frequency technology.

[0030] According to another aspect of the invention, a component and an apparatus including the component are provided, both of which can operate in the microwave region of the electromagnetic spectrum. Preferred components include a phase shifter, a varactor diode, a wireless and radio wave antenna array, a matching circuit, and an adaptive filter.

[0031] The preferred embodiments of the present invention are the subject of the dependent claims or may also be derived from the specification.

[0032] Surprisingly, it has been discovered that liquid crystal media with excellent stability, high dielectric anisotropy, suitable fast switching time, appropriate nematic phase range, high tunability, and low dielectric loss can be achieved by using compounds of formula N in liquid crystal media.

[0033] The medium according to the invention is characterized by a high brightness temperature, a wide nematic phase range, and excellent low-temperature stability (LTS). Therefore, devices containing the medium can operate under extreme temperature conditions.

[0034] The medium is further characterized by high dielectric anisotropy and low rotational viscosity. Therefore, the threshold voltage (i.e., the minimum voltage at which the device can be switched) is extremely low. Low operating voltage and low threshold voltage are desirable to enable the device to have improved switching characteristics and high energy efficiency. Low rotational viscosity enables rapid switching of the device according to the invention.

[0035] In particular, the medium containing the compound according to the invention is characterized by extremely low dielectric loss.

[0036] These properties make the medium particularly suitable for components and devices in high-frequency technologies and for applications in the microwave range, especially microwave phase-shifting devices, tunable filters, tunable metamaterial structures, and electronically beam-controlled antennas (e.g., phase array antennas).

[0037] In this document, "high-frequency technology" means the application of electromagnetic radiation with 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.

[0038] As used herein, the halogen is F, Cl, Br or I, preferably F or Cl, and particularly preferably F.

[0039] In this document, alkyl groups are straight or branched and have 1 to 15 carbon atoms, preferably straight and, unless otherwise indicated, have 1, 2, 3, 4, 5, 6 or 7 carbon atoms, and are therefore preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0040] In this article, the branched alkyl group is preferably isopropyl, dibutyl, isobutyl, isopentyl, 2-methylbutyl, 2-methylhexyl or 2-ethylhexyl.

[0041] In this document, the alkoxy group is straight-chain or branched and contains 1 to 15 carbon atoms. It is preferably straight-chain and, unless otherwise indicated, has 1, 2, 3, 4, 5, 6 or 7 carbon atoms, and is therefore preferably methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy.

[0042] In this text, the alkenyl group is preferably an alkenyl group having 2 to 15 carbon atoms, which is straight-chain or branched and contains at least one C-C double bond. It is preferably straight-chain and has 2 to 7 carbon atoms. Therefore, 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, hep-1-, -2-, -3-, -4-, -5- or -6-enyl. If the two carbon atoms of the C-C double bond are substituted, the alkenyl group may be in the form of E and / or Z isomers (trans / cis). Generally, the corresponding E isomer is preferred. Among the alkenyl groups, prop-2-enyl, but-2- and -3-enyl, and pent-3- and -4-enyl are particularly preferred.

[0043] In this document, alkynyl refers to an alkynyl group having 2 to 15 carbon atoms, which is straight-chain or branched and contains at least one C-C triple bond. Preferably, it is 1- and 2-propynyl and 1-, 2- and 3-butynyl.

[0044] In R F When the fluorinated alkyl-, alkoxy-, alkenyl or alkynyloxy group is indicated, it may be branched or unbranched. Preferably, it is unbranched, mono-, poly- or perfluorinated, preferably perfluorinated and having 1, 2, 3, 4, 5, 6 or 7 C atoms, and in the case of alkenyl, having 2, 3, 4, 5, 6 or 7 C atoms.

[0045] R P Preferred representations include CN, NCS, Cl, F, and -(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 from 0 to 7.

[0046] Compounds of general formula N are prepared precisely under known and suitable reaction conditions by methods known per se, as described in the literature (e.g., standard works such as Houben-Weyl, Methodden derorganischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart). Variations known per se but not described in more detail herein may be used.

[0047] If necessary, the starting material can also be formed in situ by reacting it immediately into a compound of general formula N, rather than separating it from the reaction mixture.

[0048] Preferred synthetic routes for compounds according to the invention are exemplified in the following schemes and further illustrated by means of working examples. Suitable synthesis is also disclosed, for example, in Juanli Li, Jian Li, Minggang Hu, Zhaoyi Che, Lingchao Mo, Xiaozhe Yang, Zhongwei An & Lu Zhang (2017) The effect of locations of triple bond at terphenyl skeleton on the properties of isothiocyanate liquidcrystals, Liquid Crystals, 44:9, 1374-1383 and can be adapted to specific desired general formula N compounds by selecting suitable starting materials.

[0049] Preferred intermediates are 2-bromopyrimidine-5-amine, 6-bromo-5-chloro-3-pyridinamine, 6-bromo-5-fluoro-3-pyridinamine, 6-bromo-2-fluoro-3-pyridinamine, 6-bromo-2,4-dichloro-3-pyridinamine, etc., all described in the literature or obtainable by synthetic procedures known to those skilled in the art. These intermediates can be reacted to yield compounds of formula N or NH via, for example, cross-coupling reactions commonly known as Suzuki, Stille, Sonogashira reactions, etc. Preferred pathways are exemplified in embodiments 1 and 2, wherein the groups and parameters have the meanings defined in claim 1.

[0050] Option 1

[0051]

[0052] Option 2

[0053]

[0054] Preferred reagents for converting compound N into compound N according to the method (Scheme 3) of the present invention are carbon disulfide, phosgene, thiocarbonyl diimidazole, di-2-pyridyl thiocarbonate, bis(dimethylthiocarbamoyl)disulfide, dimethylaminothiocarbamoyl chloride and phenyl thiochloroformate, with phosgene being particularly preferred.

[0055] Option 3

[0056]

[0057] The reactions described above and below should be considered exemplary only. Those skilled in the art can make corresponding variations of the described synthesis and also follow other suitable synthetic routes to obtain compounds of formula N.

[0058] According to a first aspect of the invention, a compound of formula N is provided, wherein R N The expression represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenyloxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups may be derived from H. The preferred alternative is an alkyl group having 1 to 12 carbon atoms.

[0059] According to a second aspect of the invention, a compound of formula N is provided, wherein the group R N R represents P , where R P Indicates halogen, CN, NCS, R F R F -O- or R F -S-, and where R F It refers to a fluorinated alkyl or fluorinated alkenyl group having up to 9 carbon atoms, preferably a perfluorinated alkyl or perfluorinated alkenyl group having up to 9 carbon atoms, very preferably CF3 or OCF3, especially OCF3.

[0060] The compounds of formula N are preferably selected from compounds of formulas N-1 to N-3, and more preferably from compounds of formulas N-1 and N-2:

[0061]

[0062] Where R N Z N1 Z N2 , and Having the above-mentioned formulas N and Y1 and Y 2 The given meanings, whether the same or different, represent H, F, Cl or CH3, preferably H, F or Cl, and t is 0 or 1.

[0063] In compounds of formula N or N-1 or N-2, and Independently selected representations

[0064] in

[0065] Or indicate and

[0066] L 1 and L 2 The same or different means of H, F, Cl or straight-chain or branched or cyclic alkyl or alkenyl groups having 1, 3, 3 or 2 to 12 C atoms respectively.

[0067] In compounds of formula N, N-1, or N-2, Z N1 and Z N2 The same or different preferred representations are -C≡C- or single bonds.

[0068] In formula N, the group Preferably selected from the following groups:

[0069]

[0070] as well as In one embodiment, the compound of formula N contains a portion of the structure

[0071]

[0072] It is selected from the following groups:

[0073]

[0074] In a preferred embodiment of the present invention, the compounds of formula N-1 and N-2 are selected from compounds of formulas N-1-1 to N-1-12 and N-2-1 to N-2-12.

[0075]

[0076]

[0077]

[0078] in

[0079] L 1 and L 2 Same or different, indicating H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclopentenyl, and

[0080] R N Y 1 and Y 2 It has the meaning given above for equations N-1 and N-2.

[0081] In a preferred embodiment, in compounds of formula N and its sub-formulas, Y 1 and Y 2 One or both (preferably both) represent H.

[0082] In another preferred embodiment, in compounds of formula N and its sub-formulas, Y 1 and Y 2 Both of them represent F.

[0083] In a preferred embodiment of the invention, the medium comprises one or more compounds selected from the group consisting of compounds of formulas I, II, and III.

[0084]

[0085] in

[0086] R 1 The CH2 group represents H, an unfluorinated alkyl group or unfluorinated alkoxy group having 1 to 17, preferably 3 to 10, carbon atoms, or an unfluorinated alkenyl group, unfluorinated alkenyloxy group or unfluorinated alkoxyalkyl group having 2 to 15, preferably 3 to 10, carbon atoms, wherein one or more CH2 groups may be derived from H. The preferred alternatives are unfluorinated alkyl or unfluorinated alkenyl groups, where n is 0, 1, or 2.

[0087] to

[0088] Each time it appears, it represents independently of each other.

[0089]

[0090] Where R L The same or different occurrences each time indicate H or an alkyl group having 1 to 6 carbon atoms, preferably H, methyl or ethyl, and particularly preferably H.

[0091] And among them

[0092]

[0093] Or indicate

[0094]

[0095] Preferred

[0096]

[0097] And if n=2, then One of the preferred options is indicated And the other is preferred to indicate

[0098]

[0099] Preferred

[0100] to

[0101] Independently representing

[0102]

[0103] More

[0104] express

[0105] express

[0106] express

[0107] R 2 The CH2 group represents H, an unfluorinated alkyl or unfluorinated alkoxy group having 1 to 17, preferably 3 to 10, carbon atoms, or an unfluorinated alkenyl, unfluorinated alkenyloxy, or unfluorinated alkoxyalkyl group having 2 to 15, preferably 3 to 10, carbon atoms, wherein one or more CH2 groups may be derived from H. The preferred alternatives are unfluorinated alkyl or unfluorinated alkenyl groups.

[0108] Z 21 This represents the trans form -CH=CH-, the trans form -CF=CF-, or -C≡C-, preferably -C≡C- or the trans form -CH=CH-, and

[0109] and

[0110] Independently representing

[0111]

[0112] Where R L Whether it is the same or different each time it appears, it means H

[0113] Or an alkyl group having 1 to 6 carbon atoms, preferably H, methyl or ethyl, particularly preferably H.

[0114] And among them

[0115] Preferred

[0116] and

[0117] Independently representing

[0118]

[0119]

[0120] Preferred representation

[0121]

[0122] and

[0123]

[0124] Preferred representation

[0125]

[0126] More

[0127]

[0128] R 3 The CH2 group represents H, an unfluorinated alkyl group or unfluorinated alkoxy group having 1 to 17, preferably 3 to 10, carbon atoms, or an unfluorinated alkenyl group, unfluorinated alkenyloxy group or unfluorinated alkoxyalkyl group having 2 to 15, preferably 3 to 10, carbon atoms, wherein one or more CH2 groups may be derived from H. The preferred alternatives are unfluorinated alkyl or unfluorinated alkenyl groups.

[0129] Z 31 and Z 32 One of them, Z is preferred 32 ; indicates trans-CH=CH-, trans-CF=CF-, or -C≡C-, and another independently indicates -C≡C-, trans-CH=CH-, trans-CF=CF-, or a single bond, preferably one of them, preferably Z. 32 ; indicates -C≡C- or trans-CH=CH-, and the other indicates a single bond, and

[0130]

[0131] to

[0132] Independently representing

[0133]

[0134]

[0135] Where R L The same or different occurrences each time indicate H or

[0136] Alkyl groups having 1 to 6 carbon atoms, preferably H, methyl, or ethyl, particularly preferably H.

[0137] And among them

[0138]

[0139] Or indicate

[0140]

[0141] Preferred

[0142] to

[0143] Independently representing

[0144]

[0145]

[0146] More

[0147]

[0148] express

[0149]

[0150] express

[0151] Specially for

[0152] express

[0153] Specially for

[0154] In compounds of formulas I, II, and III, R L H is the preferred option.

[0155] In another preferred embodiment, in the compounds of formulas I, II, and III, one or two RL (preferably one group R) L ) is not H.

[0156] In a preferred embodiment of the invention, the compound of formula I is selected from the group consisting of compounds of formulas I-1 to I-5:

[0157]

[0158] in

[0159] L 1 L 2 and L 3 The same or different occurrences each time indicate H or F, and the other groups have their respective meanings indicated above for Formula I.

[0160] Preferably

[0161] R 1 It indicates an unfluorinated alkyl group having 1 to 7 carbon atoms or an unfluorinated alkenyl group having 2 to 7 carbon atoms.

[0162] The medium preferably comprises one or more compounds of formula I-1, preferably selected from the group consisting of compounds of formula I-1a to I-1d, and preferably formula I-1b:

[0163]

[0164]

[0165] Where R 1 It has the meaning indicated above for Formula I and preferably represents an unfluorinated alkyl group having 1 to 7 C atoms or an unfluorinated alkenyl group having 2 to 7 C atoms.

[0166] The medium preferably comprises one or more compounds of formula I-2, preferably selected from the group consisting of compounds of formula I-2a to I-2e, and preferably formula I-2c.

[0167]

[0168]

[0169] Where R 1 It has the meaning indicated above for Formula I and preferably represents an unfluorinated alkyl group having 1 to 7 C atoms or an unfluorinated alkenyl group having 2 to 7 C atoms.

[0170] The medium preferably comprises one or more compounds of formula I-3, preferably selected from the group consisting of compounds of formula I-3a to I-3d, and particularly preferably compounds of formula I-3b:

[0171]

[0172] Where R 1 It has the meaning indicated above for Formula I and preferably represents an unfluorinated alkyl group having 1 to 7 C atoms or an unfluorinated alkenyl group having 2 to 7 C atoms.

[0173] The medium preferably comprises one or more compounds of formula I-4, preferably selected from the group consisting of compounds of formula I-4a to I-4e, and particularly preferably the group consisting of compounds of formula I-4b.

[0174]

[0175]

[0176] Where R 1 It has the meaning indicated above for Formula I and preferably represents an unfluorinated alkyl group having 1 to 7 C atoms or an unfluorinated alkenyl group having 2 to 7 C atoms.

[0177] The medium preferably comprises one or more compounds of formula I-5, preferably selected from the group consisting of compounds of formula I-5a to I-5d, and particularly preferably compounds of formula I-5b:

[0178]

[0179] Where R 1 It has the meaning indicated above for Formula I and preferably represents an unfluorinated alkyl group having 1 to 7 C atoms or an unfluorinated alkenyl group having 2 to 7 C atoms.

[0180] The medium preferably comprises one or more compounds of formula II, preferably selected from the group consisting of compounds of formula II-1 to II-3, and more preferably from the group consisting of compounds of formula II-1 and II-2.

[0181]

[0182] The groups appearing therein have the meanings given below Formula II above, and

[0183] Preferably

[0184] R 2 It represents H, an unfluorinated alkyl or alkoxy group having 1 to 7 carbon atoms, or an unfluorinated alkenyl group having 2 to 7 carbon atoms, and

[0185] and One of them means

[0186]

[0187] and the other independently expressed

[0188]

[0189]

[0190] Preferred

[0191]

[0192] Optimal Selection

[0193]

[0194] And preferably

[0195] R 2 C represents n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0196] n represents an integer in the range of 0 to 15, preferably in the range of 1 to 7, and especially preferably in the range of 1 to 5.

[0197] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0198] The compounds of formula II-1 are preferably selected from the group consisting of compounds of formulas II-1a to II-1e:

[0199]

[0200]

[0201] in

[0202] R 2 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0203] n represents integers that are independently represented in the range of 0 to 15, preferably in the range of 1 to 7, and particularly preferably in the range of 1 to 5.

[0204] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0205] The compounds of formula II-2 are preferably selected from the group consisting of compounds of formula II-2a and II-2b:

[0206]

[0207] in

[0208] R 2 Having the meaning indicated above and preferably representing C nH 2n+1 Or CH2=CH-(CH2) Z ,

[0209] n represents an integer in the range of 0 to 15, preferably in the range of 1 to 7, and particularly preferably in the range of 1 to 5.

[0210] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0211] The compounds of formula II-3 are preferably selected from the group consisting of compounds of formula II-3a to II-3d:

[0212]

[0213]

[0214] in

[0215] R 2 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,

[0216] n represents an integer in the range of 0 to 15, preferably in the range of 1 to 7, and particularly preferably in the range of 1 to 5.

[0217] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0218] The compounds of formula III are preferably selected from the group consisting of compounds of formulas III-1 to III-6, more preferably from the group consisting of compounds of formulas III-1, III-2, III-3 and III-4, and particularly preferably from the group consisting of compounds of formula III-1.

[0219]

[0220] in

[0221] Z 31 and Z 32 The trans-CH=CH- or trans-CF=CF- are expressed independently of each other, preferably trans-CH=CH-, and in formula III-6, alternatively, Z 31 and Z 32 One of them can represent -C≡C- and other groups having the meanings given below Formula III above.

[0222] And preferably

[0223] R 3 It represents H, an unfluorinated alkyl or alkoxy group having 1 to 7 carbon atoms, or an unfluorinated alkenyl group having 2 to 7 carbon atoms, and

[0224] to Preferred express

[0225]

[0226] Preferred

[0227]

[0228] Others, independently of each other, indicate

[0229]

[0230] Preferred

[0231]

[0232] More

[0233]

[0234] in

[0235] Or indicate

[0236] And preferably

[0237] R 3 C represents n H 2n+1 Or CH2=CH-(CH2) Z ,

[0238] n represents an integer in the range of 0 to 15, preferably in the range of 1 to 7, and particularly preferably in the range of 1 to 5.

[0239] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0240] The compounds of formula III-1 are preferably selected from the group consisting of compounds of formulas III-1a to III-1k, more preferably from the group consisting of compounds of formulas III-1a, III-1b, III-1g and III-1h, and particularly preferably from the group consisting of compounds of formulas III-1b and / or III-1h.

[0241]

[0242]

[0243] in

[0244] R 3 Having the meaning indicated above and preferably representing Cn H 2n+1 Or CH2=CH-(CH2) Z ,

[0245] n represents an integer in the range of 0 to 15, preferably in the range of 1 to 7, and particularly preferably in the range of 1 to 5.

[0246] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0247] Compounds of formula III-2 are preferably of formula III-2a to III-2l, and very preferably compounds of formula III-2b and / or III-2j:

[0248]

[0249]

[0250] in

[0251] R 3 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,

[0252] n represents an integer in the range of 0 to 15, preferably in the range of 1 to 7, and particularly preferably in the range of 1 to 5.

[0253] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0254] The compounds of formula III-5 are preferably selected from the compounds of formula III-5a:

[0255]

[0256] R 3 It has the meaning indicated above for formula III-5 and preferably represents C. n H 2n+1 ,in

[0257] n represents an integer in the range of 0 to 7, preferably in the range of 1 to 5.

[0258] In a preferred embodiment, the medium according to the invention comprises one or more compounds selected from the group consisting of compounds of formulas IIA-1-1 to IIA-1-12, most preferably IIA-1-1 or IIA-1-2:

[0259]

[0260]

[0261] in

[0262] R 1 This indicates an alkyl or alkenyl group having up to 7 carbon atoms, preferably ethyl, n-propyl, n-butyl, or n-pentyl or n-hexyl.

[0263] R L The same or different occurrences each time indicate an alkyl or alkenyl group having 1 to 5 carbon atoms, or a cycloalkyl or cycloalkenyl group each having 3 to 6 carbon atoms, preferably methyl, ethyl, n-propyl, n-butyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexylpent-1-enyl, very preferably ethyl.

[0264] And it does not include compounds of formula II-1.

[0265] Furthermore, in one particular embodiment, the liquid crystal medium according to the invention may be the same as or different from the previously preferred embodiments, and preferably comprises one or more compounds of formula IV.

[0266]

[0267] in

[0268]

[0269] express

[0270]

[0271] s is 0 or 1, preferably 1, and

[0272] Preferably

[0273]

[0274] express

[0275]

[0276] Especially preferred

[0277]

[0278] L 4 The symbol represents H or an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkenyl group having 4 to 6 carbon 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.

[0279] X4 The symbol represents H, an alkyl group having 1 to 3 carbon atoms, or a halogen, preferably H, F, or Cl, more preferably H or F, and very particularly preferably F.

[0280] R 41 To R 44 Each of these terms independently represents an unfluorinated alkyl or unfluorinated alkoxy group having 1 to 15 carbon atoms, an unfluorinated alkenyl group, an unfluorinated alkenyloxy group or an unfluorinated alkoxyalkyl group having 2 to 15 carbon atoms, or a cycloalkyl group, alkylcycloalkyl group, cycloalkenyl group, alkylcycloalkenyl group, alkylcycloalkylalkyl group or alkylcycloalkenylalkyl group having up to 15 carbon atoms, and alternatively, R 43 and R 44 One or both of them also represent H,

[0281] Preferably

[0282] R 41 and R 42 Each of these terms independently represents an unfluorinated alkyl group or an unfluorinated alkoxy group, each having 1 to 7 carbon atoms, or an unfluorinated alkenyl group, an unfluorinated alkenyloxy group, or an unfluorinated alkoxyalkyl group, each having 2 to 7 carbon atoms.

[0283] Particularly preferred

[0284] R 41 This indicates an unfluorinated alkyl group having 1 to 7 carbon atoms or an unfluorinated alkenyl group, unfluorinated alkenyloxy group, or unfluorinated alkoxyalkyl group each having 2 to 7 carbon atoms.

[0285] Particularly preferred

[0286] R 42 This indicates unfluorinated alkyl or unfluorinated alkoxy groups, each having 1 to 7 carbon atoms.

[0287] Preferably

[0288] R 43 and R 44 The term represents H, an unfluorinated alkyl group having 1 to 5 carbon atoms, an unfluorinated cycloalkyl or cycloalkenyl group having 3 to 7 carbon atoms, an unfluorinated alkylcyclohexyl or unfluorinated cyclohexylalkyl group each having 4 to 12 carbon atoms, or an unfluorinated alkylcyclohexylalkyl group having 5 to 15 carbon atoms, particularly preferably cyclopropyl, cyclobutyl, or cyclohexyl, and very particularly preferably, R. 43 and R 44 At least one of them represents an n-alkyl group, particularly preferably methyl, ethyl or n-propyl, and the other represents H or an n-alkyl group, particularly preferably H, methyl, ethyl or n-propyl.

[0289] In a preferred embodiment of the invention, the liquid crystal medium further comprises one or more compounds selected from the group consisting of compounds of formulas V, VI, VII, VIII, and IX:

[0290]

[0291] in

[0292] L 51 R represents 51 or X 51 ,

[0293] L 52 R represents 52 or X 52 ,

[0294] R 51 and R 52 The terms "H" and "unfluorinated alkyl" or "unfluorinated alkoxy" having 1 to 17, preferably 3 to 10, carbon atoms, or "unfluorinated alkenyl", "unfluorinated alkenyloxy", or "unfluorinated alkoxyalkyl" having 2 to 15, preferably 3 to 10, carbon atoms, are preferred; alkyl or unfluorinated alkenyl.

[0295] X 51 and X 52 Each of the following can independently represent H, F, Cl, -CN, SF5, a fluorinated alkyl group or a fluorinated alkoxy group having 1 to 7 carbon atoms, or a fluorinated alkenyl group, a fluorinated alkenyloxy group or a fluorinated alkoxyalkyl group having 2 to 7 carbon atoms, preferably a fluorinated alkoxy group, a fluorinated alkenyloxy group, F or Cl, and

[0296] to

[0297] Independently representing

[0298]

[0299] Preferred

[0300]

[0301] L 61 R represents 61 And if Z 61 and / or Z 62 This indicates the trans form -CH=CH- or the trans form -CF=CF-, and alternatively, it also indicates X. 61 ,

[0302] L 62 R represents 62 And if Z 61 and / or Z 62This indicates the trans form -CH=CH- or the trans form -CF=CF-, and alternatively, it also indicates X. 62 ,

[0303] R 61 and R 62 The terms "H" and "unfluorinated alkyl" or "unfluorinated alkoxy" having 1 to 17, preferably 3 to 10, carbon atoms, or "unfluorinated alkenyl", "unfluorinated alkenyloxy", or "unfluorinated alkoxyalkyl" having 2 to 15, preferably 3 to 10, carbon atoms, are preferred; alkyl or unfluorinated alkenyl.

[0304] X 61 and X 62 Each of these can independently represent F or Cl, -CN, SF5, a fluorinated alkyl or alkoxy group having 1 to 7 carbon atoms, or a fluorinated alkenyl, alkenyloxy, or alkoxyalkyl group having 2 to 7 carbon atoms.

[0305] Z 61 and Z 62 One of them represents trans-CH=CH-, trans-CF=CF-, or -C≡C-, and the other independently 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.

[0306]

[0307] to

[0308] Independently representing

[0309]

[0310] Preferred

[0311]

[0312] and

[0313] x represents 0 or 1;

[0314] L 71 R represents 71 or X 71 ,

[0315] L 72 R represents 72 or X 72 ,

[0316] R 71 and R 72The terms "H" and "unfluorinated alkyl" or "unfluorinated alkoxy" having 1 to 17, preferably 3 to 10, carbon atoms, or "unfluorinated alkenyl", "unfluorinated alkenyloxy", or "unfluorinated alkoxyalkyl" having 2 to 15, preferably 3 to 10, carbon atoms, are preferred; alkyl or unfluorinated alkenyl.

[0317] X 71 and X 72 Each of the following can independently represent H, F, Cl, -CN, -NCS, -SF5, a fluorinated alkyl or fluorinated alkoxy group having 1 to 7 carbon atoms, or a fluorinated alkenyl group having 2 to 7 carbon atoms, an unfluorinated or fluorinated alkenyloxy group, or an unfluorinated or fluorinated alkoxyalkyl group, preferably a fluorinated alkoxy group, a fluorinated alkenyloxy group, F, or Cl, and

[0318] Z 71 To Z 73 Each of these elements independently represents a trans-CH=CH-, a trans-CF=CF-, a -C≡C-, or a single bond. Preferably, one or more of these elements represent a single bond, and particularly preferably, all of them represent single bonds.

[0319] to

[0320] Independently representing

[0321]

[0322] Preferred

[0323]

[0324] R 81 and R 82 The terms "H" and "alkoxy" are independent of each other and represent 1 to 15, preferably 3 to 10, unfluorinated alkyl or alkoxy groups, or 2 to 15, preferably 3 to 10, unfluorinated alkenyl, alkenyloxy, or alkoxyalkyl groups, preferably unfluorinated alkyl or alkenyl groups.

[0325] Z 81 and Z 82 One of them represents trans-CH=CH-, trans-CF=CF-, or -C≡C-, and the other independently 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.

[0326] express

[0327]

[0328] and

[0329] Independently representing

[0330]

[0331] L 91 R represents 91 or X 91 ,

[0332] L 92 R represents 92 or X 92 ,

[0333] R 91 and R 92 The terms "H" and "alkoxy" are independent of each other and represent 1 to 15, preferably 3 to 10, unfluorinated alkyl or alkoxy groups, or 2 to 15, preferably 3 to 10, unfluorinated alkenyl, alkenyloxy, or alkoxyalkyl groups, preferably unfluorinated alkyl or alkenyl groups.

[0334] X 91 and X 92 Each of the following can independently represent H, F, Cl, -CN, -NCS, -SF5, a fluorinated alkyl or fluorinated alkoxy group having 1 to 7 carbon atoms, or a fluorinated alkenyl group having 2 to 7 carbon atoms, an unfluorinated or fluorinated alkenyloxy group, or an unfluorinated or fluorinated alkoxyalkyl group, preferably a fluorinated alkoxy group, a fluorinated alkenyloxy group, F, or Cl, and

[0335] Z 91 To Z 93 Each of these can independently represent the trans-CH=CH-, trans-CF=CF-, -C≡C-, or a single bond, preferably one or more of which represent a single bond, and particularly preferably all of them represent single bonds.

[0336] express

[0337]

[0338] to

[0339] Independently representing

[0340]

[0341] In a preferred embodiment of the invention, the liquid crystal medium comprises one or more compounds of formula V, preferably selected from formulas V-1 to V-3, preferably V-1 and / or V-2 and / or V-3, and preferably the group consisting of compounds of formulas V-1 and V-2.

[0342]

[0343] The groups appearing therein have their respective meanings as indicated above for formula V, and preferably

[0344] R 51 This indicates an unfluorinated alkyl group having 1 to 7 carbon atoms or an unfluorinated alkenyl group having 2 to 7 carbon atoms.

[0345] R 52 This indicates an unfluorinated alkyl group having 1 to 7 carbon atoms, an unfluorinated alkenyl group having 2 to 7 carbon atoms, or an unfluorinated alkoxy group having 1 to 7 carbon atoms.

[0346] X 51 and X 52 Each of these can be independently represented as F, Cl, -OCF3, -CF3, -CN, or -SF5, preferably F, Cl, -OCF3, or -CN.

[0347] The compounds of formula V-1 are preferably selected from the group consisting of compounds of formulas V-1a to V-1d, and more preferably compounds of V-1c and V-1d:

[0348]

[0349] The parameters therein have their respective meanings indicated above for equation V-1, and wherein...

[0350] Y 51 and Y 52 In each case, H or F is represented independently, and preferably...

[0351] R 51 Indicates alkyl or alkenyl, and

[0352] X 51 It represents F, Cl, or -OCF3.

[0353] The compounds of formula V-2 are preferably selected from the group consisting of compounds of formulas V-2a to V-2e and / or the group consisting of compounds of formulas V-2f and V-2g:

[0354]

[0355]

[0356] In each case, compounds of formula V-2b and V-2c do not include compounds of formula V-2a, compounds of formula V-2c do not include compounds of formula V-2b, and compounds of formula V-2g do not include compounds of formula V-2f.

[0357] The parameters described above have the custom features specified for equation V-1, and wherein...

[0358] Y 51 and Y 52 In each case, H or F is represented independently, and preferably...

[0359] Y 51 and Y 52 H represents H and another represents H or F, preferably, it also represents H.

[0360] The compounds of formula V-3 are preferably compounds of formula V-3a:

[0361]

[0362] The parameters therein have their respective meanings indicated above for equation V-1, and preferably...

[0363] X 51 F and Cl are used, with F being the preferred choice.

[0364] X 52 It represents F, Cl or -OCF3, preferably -OCF3.

[0365] The compounds of formula V-1a are preferably selected from the group consisting of compounds of formulas V-1a-1 and V-1a-2:

[0366]

[0367] in

[0368] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 ,in

[0369] n represents an integer in the range of 1 to 7, preferably in the range of 1 to 6, and particularly preferably in the range of 3 to 5.

[0370] The compounds of formula V-1b are preferably compounds of formula V-1b-1:

[0371]

[0372] in

[0373] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 ,in

[0374] n represents an integer in the range of 1 to 7, preferably in the range of 1 to 6, and particularly preferably in the range of 3 to 5.

[0375] The compounds of formula V-1c are preferably selected from the group consisting of compounds of formulas V-1c-1 to V-1c-4, and particularly preferably selected from the group consisting of compounds of formulas V-1c-1 and V-1c-2.

[0376]

[0377]

[0378] in

[0379] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 ,in

[0380] n represents an integer in the range of 1 to 7, preferably in the range of 1 to 6, and particularly preferably in the range of 3 to 5.

[0381] The compounds of formula V-1d are preferably selected from the group consisting of compounds of formula V-1d-1 and V-1d-2, and are particularly preferred to be compounds of formula V-1d-2:

[0382]

[0383] in

[0384] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 ,in

[0385] n represents an integer in the range of 1 to 7, preferably in the range of 1 to 6, and particularly preferably in the range of 3 to 5.

[0386] The compounds of formula V-2a are preferably selected from the group consisting of compounds of formula V-2a-1 and V-2a-2, and are particularly preferred to be compounds of formula V-2a-1:

[0387]

[0388] in

[0389] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0390] R 52 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z-CH = CH2, and where

[0391] n and m, independently representing integers in the range of 1 to 7, preferably in the range of 1 to 6, and particularly preferably in the range of 3 to 5, and

[0392] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0393] R 51 With R 52 The preferred combination, especially in the case of formula V-2a-1, is (C n H 2n+1 With C m H 2m+1 ), (C n H 2n+1 With OC m H 2m+1 (CH2=CH-(CH2)) Z With C m H 2m+1 (CH2=CH-(CH2)) Z With OC m H 2m+1 ) and (C n H 2n+1 With (CH2) Z -CH=CH2).

[0394] The preferred compound of formula V-2b is the compound of formula V-2b-1:

[0395]

[0396] in

[0397] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0398] R 52 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0399] n and m, independently representing integers in the range of 1 to 7, preferably in the range of 1 to 6, and particularly preferably in the range of 3 to 5, and

[0400] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0401] Here, R 51 With R 52 The preferred combination, especially C n H 2n+1 and C m H 2m+1 The preferred compound of formula V-2c is the compound of formula V-2c-1:

[0402]

[0403] in

[0404] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0405] R 52 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0406] n and m, independently representing integers in the range of 1 to 7, preferably in the range of 1 to 6, and particularly preferably in the range of 3 to 5, and

[0407] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0408] Here, (R) 51 With R 52 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ).

[0409] The preferred compounds of formula V-2d are those of formula V-2d-1:

[0410]

[0411] in

[0412] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0413] R 52 Having the meaning indicated above and preferably representing C m H2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0414] n and m are independently represented as integers in the range of 1 to 7, preferably in the range of 1 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.

[0415] Here, (R) 51 With R 52 The preferred combination of (C) n H 2n+1 With C m H 2m+1 The preferred compound of formula V-2e is the compound of formula V-2e-1:

[0416]

[0417] in

[0418] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0419] R 52 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0420] n and m, independently representing integers 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

[0421] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0422] Here, (R) 51 With R 52 The preferred combination of (C) n H 2n+1 With OC m H 2m+1 ).

[0423] The preferred compound of formula V-2f is the compound of formula V-2f-1:

[0424]

[0425] in

[0426] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0427] R 52 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0428] n and m, independently representing integers 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

[0429] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0430] Here, (R) 51 With R 52 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0431] The preferred compound of formula V-2g is the compound of formula V-2g-1:

[0432]

[0433] in

[0434] R 51 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0435] R 52 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0436] n and m, independently representing integers 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

[0437] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0438] Here, (R) 51 With R 52 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With OC m H 2m+1 ).

[0439] The compounds of formula VI are preferably selected from the group consisting of compounds of formulas VI-1 to VI-5:

[0440]

[0441]

[0442] in

[0443] Z 61 and Z 62 The expression represents -C≡C-, trans-CH=CH-, or trans-CF=CF-, preferably -C≡C- or trans-CH=CH-, and other groups and parameters that appear have the meanings given below Formula VI above.

[0444] And preferably

[0445] R 61 and R 62 Each of these can be independently represented by H, an unfluorinated alkyl or alkoxy group having 1 to 7 carbon atoms, or an unfluorinated alkenyl group having 2 to 7 carbon atoms.

[0446] X 62 It represents F, Cl, -OCF3, or -CN.

[0447] The compounds of formula VI-1 are preferably selected from the group consisting of compounds of formula VI-1a and VI-1b, and more preferably from the group consisting of compounds of formula VI-1a:

[0448]

[0449] in

[0450] R 61 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0451] R 62 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0452] n and m, independently representing integers 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

[0453] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0454] Here, (R) 61 With R 62 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 In the case of formula VI-1a, it is particularly preferred that (C) n H 2n+1 With C m H 2m+1 ), and in the case of formula VI-1b, it is particularly preferred to be (C n H 2n+1 With OC m H 2m+1 ).

[0455] The compounds of formula VI-3 are preferably selected from compounds of formulas VI-3a to VI-3e:

[0456]

[0457] The parameters described herein have the meanings given below Equation VI-3 above and are preferably...

[0458] R 61 Having the meaning indicated above and preferably representing C n H 2n+1 ,in

[0459] n represents an integer in the range of 1 to 7, preferably in the range of 1 to 5, and

[0460] X 62 It represents -F, -Cl, -OCF3, or -CN.

[0461] The compounds of formula VI-4 are preferably selected from compounds of formulas VI-4a to VI-4e:

[0462]

[0463] The parameters mentioned above have the meanings given below Equation VI-4 and are preferably...

[0464] R 61 Having the meaning indicated above and preferably representing C n H 2n+1 ,in

[0465] n represents an integer in the range of 1 to 7, preferably in the range of 1 to 5, and

[0466] X 62 It represents F, Cl, OCF3, or -CN.

[0467] The compounds of formula VI-5 are preferably selected from formulas VI-5a to VI-5d, and preferably compounds of formula VI-5b:

[0468]

[0469]

[0470] The parameter described above has the meaning given below Equation VI-5, and preferably R 61 Having the meaning indicated above and preferably representing C n H 2n+1 Where n represents an integer in the range of 1 to 7, preferably in the range of 1 to 5, and X 62 It can be represented as -F, -Cl, -OCF3 or -CN, with -OCF3 being particularly preferred.

[0471] The compounds of formula VII are preferably selected from the group consisting of compounds of formulas VII-1 to VII-6:

[0472]

[0473]

[0474] The compounds of formula VII-6 do not include the compounds of formula VII-5, and

[0475] The parameters therein have their respective meanings as indicated above for equation VII.

[0476] Y71 Y 72 Y 73 H or F can be represented independently of each other.

[0477] And preferably

[0478] R 71 This refers to unfluorinated alkyl or alkoxy groups having 1 to 7 carbon atoms, or unfluorinated alkenyl groups having 2 to 7 carbon atoms.

[0479] R 72 This refers to unfluorinated alkyl or alkoxy groups having 1 to 7 carbon atoms, or unfluorinated alkenyl groups having 2 to 7 carbon atoms.

[0480] X 72 It represents F, Cl; NCS or -OCF3, preferably F or NCS, and

[0481] Particularly preferred R 71 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0482] R 72 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0483] n and m, independently representing integers 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

[0484] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0485] The compounds of formula VII-1 are preferably selected from the group consisting of compounds of formulas VII-1a to VII-1d:

[0486]

[0487]

[0488] Where X 72 It has the meaning given above for equation VII-2 and

[0489] R 71 Having the meaning indicated above and preferably representing C n H 2n+1 ,in

[0490] n represents 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.

[0491] z represents 0, 1, 2, 3, or 4, preferably 0 or 2, and

[0492] X 72 The preferred option is represented by F.

[0493] The compounds of formula VII-2 are preferably selected from formulas VII-2a and VII-2b, and particularly preferably from the group consisting of compounds of formula VII-2a:

[0494]

[0495] in

[0496] R 71 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0497] R 72 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0498] n and m, independently representing integers 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

[0499] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0500] Here, (R) 71 With R 72 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0501] The compounds of formula VII-3 are preferably compounds of formula VII-3a:

[0502]

[0503] in

[0504] R 71 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0505] R 72 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0506] n and m, independently representing integers 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

[0507] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0508] Here, (R) 71 With R 72 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0509] The compounds of formula VII-4 are preferably compounds of formula VII-4a:

[0510]

[0511] in

[0512] R 71 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0513] R 72 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z-CH = CH2, and where

[0514] n and m, independently representing integers 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

[0515] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0516] Here, (R) 71 With R 72 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0517] The compounds of formula VII-5 are preferably selected from formulas VII-5a and VII-5b, and more preferably from the group consisting of compounds of formula VII-5a:

[0518]

[0519] in

[0520] R 71 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0521] R 72 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0522] n and m, independently representing integers 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

[0523] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0524] Here, (R) 71 With R 72 The preferred combination of (C) n H 2n+1 With C mH 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0525] The compounds of formula VII-6 are preferably selected from the group consisting of compounds of formula VII-6a and VII-6b:

[0526]

[0527] in

[0528] R 71 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0529] R 72 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0530] n and m, independently representing integers 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

[0531] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0532] Here, (R) 71 With R 72 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0533] The compounds of formula VII-7 are preferably selected from the group consisting of compounds of formula VII-7a to VII-7d:

[0534]

[0535] in

[0536] R 71 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,

[0537] X 72 Indicates F, -OCF3, or -NCS.

[0538] n represents 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.

[0539] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0540] The compounds of formula VIII are preferably selected from the group consisting of compounds of formula VIII-1 to VIII-3, more preferably, these compounds of formula VIII are mainly composed of them, even more preferably substantially composed of them, and very particularly preferably entirely composed of them:

[0541]

[0542]

[0543] in

[0544] Y 81 and Y 82 One of them represents H or the other represents H or F, and

[0545] R 81 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0546] R 82 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0547] n and m, independently representing integers 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

[0548] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0549] Here, (R) 81 With R82 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0550] The compounds of formula VIII-1 are preferably selected from the group consisting of compounds of formula VIII-1a to VIII-1c:

[0551]

[0552] in

[0553] R 81 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0554] R 82 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0555] n and m, independently representing integers 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

[0556] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0557] Here, (R) 81 With R 82 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0558] The compounds of formula VIII-2 are preferably compounds of formula VIII-2a:

[0559]

[0560] in

[0561] R 81 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0562] R 82 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0563] n and m, independently representing integers 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

[0564] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0565] Here, (R) 81 With R 82 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ), (C n H 2n+1 With OC m H 2m+1 ) and (CH2=CH-(CH2) Z With C m H 2m+1 (C) is particularly preferred. n H 2n+1 With C m H 2m+1 ).

[0566] The compounds of formula VIII-3 are preferably compounds of formula VIII-3a:

[0567]

[0568] in

[0569] R 81 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2)Z ,and

[0570] R 82 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0571] n and m, independently representing integers 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

[0572] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0573] Here, (R) 81 With R 82 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 The compounds of formula IX are preferably selected from the group consisting of compounds of formulas IX-1 to IX-3.

[0574]

[0575] The parameters therein have their respective meanings as indicated above below Equation IX, and preferably

[0576] to One of them means

[0577]

[0578] And among them

[0579] R 91 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0580] R 92 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0581] n and m, independently representing integers 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

[0582] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0583] Here, (R) 91 With R 92 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 ).

[0584] The compounds of formula IX-1 are preferably selected from the group consisting of compounds of formulas IX-1a to IX-1e:

[0585]

[0586]

[0587] The parameters mentioned above have the meanings given above and are preferably...

[0588] R 91 Having the meaning indicated above and preferably representing C n H 2n+1 ,and

[0589] n represents an integer in the range of 0 to 15, preferably in the range of 1 to 7, and particularly preferably in the range of 1 to 5.

[0590] X 92 The preferred representation is F or Cl.

[0591] The compounds of formula IX-2 are preferably selected from the group consisting of compounds of formulas IX-2a and IX-2b:

[0592]

[0593] in

[0594] R 91 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0595] R 92 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H2m+1 Or (CH2) Z -CH = CH2, and where

[0596] n and m, independently representing integers 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

[0597] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0598] Here, (R) 91 With R 92 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ).

[0599] The compounds of formula IX-3 are preferably compounds of formulas IX-3a and IX-3b:

[0600]

[0601] in

[0602] R 91 Having the meaning indicated above and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0603] R 92 Having the meaning indicated above and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, and where

[0604] n and m, independently representing integers 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

[0605] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0606] Here, (R) 91 With R 92 The preferred combination of (C) n H 2n+1 With C m H 2m+1 ) and (C n H 2n+1 With OC m H 2m+1 (C) is particularly preferred. n H 2n+1With OC m H 2m+1 ).

[0607] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula X.

[0608]

[0609] in

[0610] R 101 The symbol represents H, an alkyl or alkoxy group having 1 to 15, preferably 3 to 10, carbon atoms, or an unfluorinated alkenyl group, unfluorinated alkenyloxy group, or unfluorinated alkoxyalkyl group having 2 to 15, preferably 3 to 10, carbon atoms, preferably alkyl or alkenyl.

[0611] X 101 This refers to H, F, Cl, -CN, SF5, NCS, a fluorinated alkyl group or fluorinated alkoxy group having 1 to 7 carbon atoms, or a fluorinated alkenyl group, fluorinated alkenyloxy group or fluorinated alkoxyalkyl group having 2 to 7 carbon atoms, preferably a fluorinated alkoxy group, a fluorinated alkenyloxy group, F, Cl or NCS, particularly preferably NCS.

[0612] Y 101 Indicates methyl, ethyl, or Cl.

[0613] Y 102 It represents H, methyl, ethyl, F or Cl, preferably H or F.

[0614] Z 101 Z 102 Same or different indicates a single bond, -CH=CH-, -CF=CF-, or -C≡C-.

[0615]

[0616] and

[0617] Independently representing

[0618]

[0619] Preferred

[0620]

[0621] And among them

[0622] Or indicate and

[0623] n is 0 or 1.

[0624] Preferably, the compound of formula X is selected from sub-formulas X-1 and X-2.

[0625]

[0626] The groups and parameters that appear have the same meaning as given above for formula X.

[0627] Particularly preferably, the medium according to the invention comprises one or more compounds selected from the group consisting of compounds of formula X-1-1 to X-1-9.

[0628]

[0629]

[0630] In a preferred embodiment, the medium according to the invention comprises one or more compounds of formula XI.

[0631]

[0632] in

[0633] R S The expression represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenyloxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2 groups may be derived from H. Substitution, and one or more of the H atoms can be substituted by F,

[0634] and

[0635] Each time it appears, it represents independently of each other.

[0636]

[0637]

[0638] Where R L The same or different occurrences each time indicate H,

[0639] Cl or straight-chain, branched, or cyclic alkyl groups having 1 to 6 carbon atoms,

[0640] L S1 L S2 Same or different, indicating H, Cl or F,

[0641] R S1 R S2 The same or different indicates H, an alkyl or alkenyl group having up to 6 carbon atoms, or a cyclopropyl, cyclobutyl, cyclopentenyl, or cyclopentyl group.

[0642] R Th1 R Th2 Same or different, indicating H, alkyl or alkenyl or alkoxy with up to 6 carbon atoms, or cyclopropyl, cyclobutyl, cyclopentenyl or cyclopentyl.

[0643] Z S1 Z S2 Z S3 Same or different indicates -CH=CH-, -CH=CF-, -CF=CH-, -CF=CF-, -C≡C-, or a single bond.

[0644] a and b are either the same or different, either 0 or 1.

[0645] Preferably, the compound of formula XI is selected from the group consisting of compounds of formulas XI-1 to XI-24:

[0646]

[0647]

[0648]

[0649]

[0650] The groups appearing therein have the meanings given above for formula XI and are preferably...

[0651] R S It represents an alkyl or alkenyl group having 2 to 6 carbon atoms, wherein one or more CH2 groups can be derived from an alkyl or alkenyl group. Replacement, R S1 and R S2 Same or different, indicating H or an alkyl group having 1 to 6 carbon atoms.

[0652] H, R are preferred. S3 The group represents H, F, or an alkyl group having up to 6 carbon atoms, or a cyclopropyl group, preferably H, F, or an ethyl group, and very preferably H.

[0653] L S1 and L S2 The same or different is represented by H or F, with F being preferred.

[0654] Preferably, the medium according to the invention comprises one or more compounds of formula T.

[0655]

[0656] in

[0657] R T Indicates halogen, CN, NCS, R F RF -O- or R F -S-, where R F It indicates a fluorinated alkyl or fluorinated alkenyl group having up to 12 carbon atoms.

[0658] and

[0659] Each time it appears, it represents independently of each other.

[0660]

[0661] L 4 and L 5 Same or different, indicating F, Cl or straight-chain or branched or cyclic alkyl or alkenyl groups each having up to 12 C atoms;

[0662] Z T3 Z T4 Same or different indicates -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C- or a single bond, and

[0663] t is 0 or 1.

[0664] In a preferred embodiment, the liquid crystal medium according to the invention comprises one or more compounds selected from the group consisting of compounds of formulas T-1a to T-3b:

[0665]

[0666]

[0667] in and It has the meaning given above and

[0668] n can be 1, 2, 3, 4, 5, 6 or 7, preferably 1, 2, 3 or 4, and particularly preferably 1.

[0669] In a particularly preferred embodiment of the invention, the medium comprises one or more compounds selected from formulas T-1a and T-2a.

[0670] The preferred compounds of formula T-1a are selected from the group consisting of compounds of the following formulas:

[0671]

[0672]

[0673] Where n can be 1, 2, 3 or 4, preferably 1.

[0674] The preferred compounds of formula T-2a are selected from the group consisting of compounds of the following formulas:

[0675]

[0676] Where n can be 1, 2, 3 or 4, preferably 1.

[0677] Very preferably, the medium according to the invention comprises one or more compounds of formula T-1a-5.

[0678] The medium according to the invention comprises one or more chiral dopants. Preferably, the absolute value of the helical twist force (HTP) of these chiral dopants is in the range of 1 μm. -1 Up to 150μm -1 Within the range, preferably within 10 μm -1 Up to 100μm -1 Within the range. In the case where the medium contains two or more chiral dopants, these may have opposite signs for their HTP values. For some specific embodiments, this condition is preferred because it allows for some compensation of the chirality of the respective compounds, and thus can be used to compensate for various temperature-dependent properties of the resulting medium in the device. However, generally, it is preferred that most, preferably all, chiral compounds present in the medium according to the invention have the same sign for their HTP values.

[0679] Preferably, the chiral dopants present in the medium according to this application are mesocrystalline compounds, and most preferably they themselves exhibit a mesocrystalline phase.

[0680] In a preferred embodiment of the invention, the medium comprises two or more chiral compounds that all have the same algebraic symbol for HTP.

[0681] The temperature dependence of HTP on individual compounds can be high or low. The temperature dependence of the pitch of the medium can be compensated by mixing compounds with different HTP temperatures in appropriate ratios.

[0682] For optically active components, a variety of chiral dopants are available to those skilled in the art, some of which are commercially available, such as cholesterol nonanoate, R- and S-811, R- and S-1011, R- and S-2011, R- and S-3011, R- and S-4011, or CB15 (all from Merck KGaA, Darmstadt).

[0683] Particularly suitable dopants are compounds containing one or more chiral groups and one or more mesomorphic groups, or one or more aromatic or alicyclic groups that form mesomorphic groups with chiral groups.

[0684] Suitable chiral groups are, for example, chiral branched hydrocarbon groups, chiral ethylene glycol, binaphthol, or dioxolane, and are also selected from mono- or polyvalent chiral groups such as sugar derivatives, sugar alcohols, sugar acids, lactic acids, chiral substituted diols, steroid derivatives, terpene derivatives, amino acids, or sequences of several (preferably 1 to 5) amino acids.

[0685] Preferred chiral groups are sugar derivatives, such as glucose, mannose, galactose, fructose, arabinose, and dextrose; sugar alcohols, such as sorbitol, mannitol, idoteol, galactitol, or their dehydrated derivatives, particularly disohydrated hexotols, such as disohydrated sorbitol (1,4:3,6-disohydrated-D-sorbitol, isosorbitol), disohydrated mannitol (isosorbitol), or disohydrated idoteol (isoidoteol); sugar acids, such as gluconic acid, gulonic acid, and ketogulonic acid; chiral substituted glycol groups, such as mono- or oligomeric polyethylene glycol or propylene glycol, wherein one or more CH2 groups are substituted with alkyl or alkoxy groups; amino acids, such as alanine, valine, phenylglycerol, etc. A sequence of amino acids or phenylalanine or 1 to 5 of these amino acids; steroid derivatives, such as cholesterol or bile acid groups; terpene derivatives, such as menthyl, neomenthyl, campheyl, pinenyl, terpineyl, isolongifolyl, frangyl, carreyl, myrthenyl, nopyl, geraniyl, linaloyl, neryl, citronellyl, or dihydrocitronellyl.

[0686] The medium according to the invention preferably contains a chiral dopant selected from the group consisting of known chiral dopants. Suitable chiral groups and mesocrystalline chiral compounds are described, for example, in DE 34 25 503, DE 35 34 777, DE 35 34 778, DE 35 34 779 and DE 35 34 780, DE 43 42 280, EP 01 038 941 and DE 195 41 820. Examples also include compounds listed in Table F below.

[0687] The chiral compounds preferred for use according to the present invention are selected from the following formulas.

[0688] Chiral dopants selected from compounds of the following formulas Al to A-III and A-Ch are particularly preferred:

[0689]

[0690]

[0691] in

[0692] R a11 R a12 and R b12 Each of the above can independently represent an alkyl group having 1-15 carbon atoms, wherein, in addition, one or more non-adjacent CH2 groups can each be independently represented by -C(R) z )=C(R z -, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- are substituted in such a way that the O and / or S atoms are not directly connected to each other, and wherein, in addition, one or more H atoms may be substituted by F, Cl, Br, I or CN, preferably alkyl, more preferably n-alkyl, provided that R a12 With R b12 different

[0693] R a21 and R a22 Each of the above can independently represent an alkyl group having 1-15 carbon atoms, wherein, in addition, one or more non-adjacent CH2 groups can each be independently represented by -C(R) z )=C(R z -, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- are substituted in such a way that the O and / or S atoms are not directly connected to each other, and wherein, in addition, one or more H atoms can be replaced by F, Cl, Br, I or CN, preferably both being alkyl, more preferably n-alkyl.

[0694] R a31 R a32 and R b32 Each of the above can independently represent an alkyl group having a straight chain and branches of 1-15 carbon atoms, wherein, in addition, one or more non-adjacent CH2 groups can each be independently separated by -C(R) z )=C(R z -, -C≡C-, -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O- are substituted in such a way that the O and / or S atoms are not directly connected to each other, and wherein, in addition, one or more H atoms can be substituted by F, Cl, Br, I, or CN.

[0695] Alkyl groups are preferred, and n-alkyl groups are more preferred, provided that R a32 With R b32 different,

[0696] R z It can be represented by H, CH3, F, Cl, or CN, with H or F being preferred.

[0697] R8 With the R given above a11 One meaning is that alkyl is preferred, and more preferably a n-alkyl group having 1-15 carbon atoms.

[0698] Z 8 It represents -C(O)O-, CH2O, CF2O or a single bond, preferably -C(O)O-.

[0699] A 11 As shown in A below 12 Defined, or alternatively represented

[0700]

[0701] A 12 express

[0702]

[0703] Preferably

[0704]

[0705] in

[0706] L 12 Each occurrence independently represents a halogen, CN, or an alkyl, alkenyl, alkoxy, or alkenyloxy group having up to 12 carbon atoms, and one or more H atoms are optionally replaced by a halogen, preferably methyl, ethyl, Cl, or F, with F being particularly preferred.

[0707] A 21 express

[0708]

[0709] A 22 With targeting A 12 The meaning given

[0710] A 31 With targeting A 11 The given meaning,

[0711] Or alternatively represent

[0712]

[0713] A 32 With targeting A 12 The meaning given.

[0714] n2 is either 0, 1, or 2 each time it appears, and

[0715] n3 is 1, 2, or 3.

[0716] n4 is either 0 or 1, preferably 0, and

[0717] r can be 0, 1, 2, 3 or 4.

[0718] Dopants are particularly preferred from the group consisting of compounds of the following formula:

[0719]

[0720]

[0721] in

[0722] m is an integer from 1 to 9, either identically or differently, in each occurrence.

[0723] n is an integer from 2 to 9, either the same or different, each time it appears.

[0724] The particularly preferred compounds of formula A are compounds of formula A-III.

[0725] Further preferred dopants are derivatives of isosorbide, isomannitol, or isoadurel of formula A-IV:

[0726]

[0727] Among them, groups for

[0728] (desaturated sorbitol),

[0729] (Disohydrated mannitol), or

[0730] (disohydrated idutitol),

[0731] The preferred option is dehydrosorbitol.

[0732] And chiral ethylene glycols, such as diphenylethylene glycol (hydrogenated benzoin), especially mesocrystalline hydrogenated benzoin derivatives of the following formula AV:

[0733]

[0734] Including (S,S) enantiomers not shown,

[0735] in

[0736]

[0737] and

[0738] Each is independently 1,4-phenylene (which can also be composed of L-mono-,

[0739] Di- or tri-substituted) or 1,4-cyclohexylene,

[0740] L is H, F, Cl, CN, or an alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, or alkoxy carbonyl group having 1 to 7 carbon atoms, optionally halogenated.

[0741] c is 0, 1, or 2.

[0742] X is CH2 or -C(O)-,

[0743] Z 0 It is -COO-, -OCO-, -CH2CH2- or a single bond, and

[0744] R 0 It is an alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl or alkyl carbonyloxy group having 1-12 carbon atoms.

[0745] Examples of compounds of formula IV are:

[0746]

[0747]

[0748] Where R IV It is an alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl or alkyl carbonyloxy group having up to 12 carbon atoms.

[0749] Compounds of formulas A-IV are described in WO 98 / 00428. Compounds of formula AV are described in GB-A-2,328,207.

[0750] Very particularly preferred dopants are chiral binaphthyl derivatives as described in WO 02 / 94805, chiral binaphthol acetal derivatives as described in WO 02 / 34739, chiral TADDOL derivatives as described in WO 02 / 06265, and chiral dopants having at least one fluorinated bridging group and a terminal or central chiral group as described in WO 02 / 06196 and WO 02 / 06195.

[0751] Chiral compounds of formula A-VI are particularly preferred.

[0752]

[0753] in

[0754] X 1 X 2 Y 1 and Y 2Each of the following is independently F, Cl, Br, I, CN, SCN, SF5, a straight-chain or branched alkyl group having 1 to 25 carbon atoms, which is unsubstituted or monosubstituted or polysubstituted with F, Cl, Br, I or CN, and wherein, in addition, one or more non-adjacent CH2 groups may be independently substituted with -O-, -S-, -NH-, NR- x The substitutions are made of -, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH-, or -C≡C-, wherein the O and / or S atoms are not directly bonded to each other, and the substitutions are polymerizable groups, or cycloalkyl or aryl groups having up to 20 carbon atoms, which may be optionally mono- or poly-substituted with halogens (preferably F) or polymerizable groups.

[0755] x 1 and x 2 Each is independently 0, 1, or 2.

[0756] y 1 and y 2 Each is independently 0, 1, 2, 3, or 4.

[0757] B 1 and B 2 Each is an aromatic or partially or fully saturated aliphatic six-membered ring, wherein one or more CH groups may be substituted with N and one or more non-adjacent CH2 groups may be substituted with O or S.

[0758] W 1 and W 2 Each is independent of the others -(Z) 1 -A 1 ) m1 -(Z 2 -A 2 ) m2 -R, and one of these two is replaced by R 1 Or A 3 However, the two cannot both be H, or

[0759] for

[0760] or

[0761]

[0762] U 1 and U 2 Each can be independently represented as CH2, O, S, CO, or CS.

[0763] V 1 and V 2 Each is independently (CH2) nOne to four non-adjacent CH2 groups may each be substituted with O or S, and V 1 and V 2 One of them can represent a single bond, and in it

[0764] for In this case,

[0765] Both are single bonds.

[0766] n is 1, 2 or 3

[0767] Z 1 and Z 2 Each of these can be independently represented as -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR x -、-NR x The following groups are combinations of two of the following: -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-, where no two O and / or S and / or N atoms are directly bonded to each other. Preferably, they are -CH=CH-COO-, or -COO-CH=CH-, or single bonds.

[0768] R x Indicates an alkyl group having 1 to 6 carbon atoms.

[0769] A 1 A 2 and A 3 Each of these groups is independently 1,4-phenylene (one or both non-adjacent CH groups may be N-substituted), 1,4-cyclohexylene (one or both non-adjacent CH2 groups may be O or S-substituted), 1,3-dioxacyclopentane-4,5-diyl, 1,4-cyclohexenyl, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthyl-2,6-diyl, decahydronaphthyl-2,6-diyl, or 1,2,3,4-tetrahydronaphthyl-2,6-diyl, wherein each of these groups may be L-monosubstituted or polysubstituted, and in addition, A 1 It can be a single key.

[0770] L is a halogen atom, preferably F, CN, NO2, an alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkoxycarbonyloxy group having 1 to 7 carbon atoms, wherein one or more H atoms may be replaced by F or Cl.

[0771] m1 is 0 or 1.

[0772] m2 is independently 0, 1, or 2 in each case.

[0773] and

[0774] R and R 1 Each of the following is an independent straight-chain or branched alkyl group having 1 or 3 to 25 carbon atoms: H, F, Cl, Br, I, CN, SCN, SF5, which may be monosubstituted or polysubstituted with F, Cl, Br, I, or CN, and one or more non-adjacent CH2 groups may be respectively substituted with -O-, -S-, -NH-, or -NR. 0 The following are substitutions: -, -CO-, -COO-, -OCO-, -O-COO-, -S-CO-, -CO-S-, -CH=CH-, or -C≡C-, wherein there are no two O and / or S atoms directly bonded to each other, or polymerizable groups.

[0775] Chiral binaphthyl derivatives of formula A-VI-1 are particularly preferred.

[0776]

[0777] Wherein ring B represents 1,4-phenylene or 1,4-cyclohexylene, which may be mono- or poly-substituted with F, and R 0 Indicates an alkyl group having 1 to 7 carbon atoms.

[0778] Z 0 This represents -O-, -COO-, -OCO-, -OCH2-, -CH2O-, -CH2CH2-, or -CH=CH-, where b is 0, 1, or 2.

[0779] In particular, those selected from formulas A-VI-1a to A-VI-1c:

[0780]

[0781] Where R 0 and Z 0 It has the meaning defined above and preferably

[0782] R 0 This indicates an alkyl group having 1 to 4 carbon atoms, and

[0783] Z 0 It is -OC(O)- or a single bond.

[0784] The concentration of one or more chiral dopants in the LC medium is preferably from 0.001% to 20%, more preferably from 0.05% to 5%, more preferably from 0.1% to 2%, and most preferably from 0.5% to 1.5%. These preferred concentration ranges are particularly applicable to chiral dopants S-4011 or R-4011 (both derived from Merck KGaA) and chiral dopants having the same or similar HTP. For chiral dopants having higher or lower absolute HTP values ​​compared to S-4011, these preferred concentrations must be reduced, increasing proportionally to the ratio of their HTP value to that of S-4011.

[0785] The pitch p of the LC medium or bulk mixture according to the invention is preferably in the range of 5 to 50 μm, more preferably 8 to 30 μm, and particularly preferably 10 to 20 μm.

[0786] Preferably, the medium according to the invention comprises a stabilizer selected from the group consisting of compounds of formulas ST-1 to ST-19.

[0787]

[0788]

[0789]

[0790]

[0791] in

[0792] R ST The group represents H, an alkyl or alkoxy group having 1 to 15 carbon atoms, wherein, furthermore, one or more CH2 groups in these groups may be independently converted to -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, and -O-CO- substitutions are used, where the O atoms are not directly connected to each other, and one or more H atoms can be substituted with halogens.

[0793] express

[0794]

[0795]

[0796] Z STEach of these can independently represent -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond.

[0797] L 1 and L 2 Each can be independently represented as F, Cl, CF3, or CHF2.

[0798] p represents 1 or 2, and

[0799] q represents 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Among compounds of formula ST, compounds of the following formula are particularly preferred.

[0800]

[0801] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n

[0802] =1 or 7

[0803]

[0804] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n

[0805] =3

[0806]

[0807] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n

[0808] =3

[0809]

[0810]

[0811] In compounds of formula ST-3a and ST-3b, n preferably represents 3. In compounds of formula ST-2a, n preferably represents 7.

[0812] The mixture according to the invention particularly preferably comprises a stabilizer selected from the group consisting of one or more compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1 and ST-12:

[0813]

[0814]

[0815] The compounds of formulas ST-1 to ST-19 are preferably present in the liquid crystal mixture according to the invention in an amount of 0.005 to 0.5% based on the mixture.

[0816] If the mixture according to the invention contains two or more compounds selected from the group consisting of compounds of formulas ST-1 to ST-19, then in the case of two compounds, the concentration is correspondingly increased to 0.01 to 1% based on the mixture.

[0817] However, based on the mixtures according to the invention, the total proportion of compounds of formulas ST-1 to ST-18 should not exceed 2%.

[0818] Other mesocrystalline compounds not explicitly mentioned above may also be used optionally and advantageously in the media according to the invention. Such compounds are known to those skilled in the art.

[0819] In a preferred embodiment of the invention, the total concentration of the compound of formula N in the liquid crystal medium is 5% or higher, preferably 8% or higher, very preferably 10% or higher, and particularly preferably 12% or higher.

[0820] In a preferred embodiment of the invention, the liquid crystal medium preferably contains a total of 2% to 40%, more preferably 5% to 30%, and particularly preferably 8% to 25% of a compound of formula N.

[0821] In a preferred embodiment of the invention, the liquid crystal medium comprises a total of 5% to 45%, preferably 10% to 40%, and particularly preferably 15% to 35% of one or more compounds of formula T (preferably selected from formulas T-1a and T-2a, and very preferably selected from T-1a-5 and T-2a-4).

[0822] In a preferred embodiment of the invention, the liquid crystal medium comprises a total of 5% to 35%, preferably 10% to 30%, and particularly preferably 15% to 25% of one or more compounds of formula T-1a.

[0823] In a preferred embodiment of the invention, the liquid crystal medium comprises a total of 5% to 35%, preferably 10% to 30%, and particularly preferably 15% to 25% of one or more compounds of formula T-1a, and an additional 5% to 15% of one or more compounds of formula T-2a-4.

[0824] In a preferred embodiment, the medium comprises one or more compounds of formula I, preferably formula I-2 or I-3, with a total concentration of 1% to 25%, more preferably 2% to 20%, and particularly preferably 5% to 15%.

[0825] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula II, preferably formula II-1, at a total concentration of 5% to 35%, more preferably 10% to 30%, and particularly preferably 15% to 25%.

[0826] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula IIA-1, wherein the total concentration is 5% to 25%, more preferably 8% to 20%, and particularly preferably 12% to 17%.

[0827] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula II-1, with a total concentration of 30% or less, more preferably 25% or less, and particularly preferably 20% or less.

[0828] 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, with a total concentration of 15% to 70%, more preferably 25% to 60%, and particularly preferably 35% to 50%.

[0829] In a preferred embodiment, the medium comprises one or more compounds of formula N and I and II and / or IIA, and III and T, preferably having a total concentration of 90% or higher, more preferably 95%, 96% or 97% or higher, very preferably 98% or higher, and particularly 99% or higher.

[0830] In a preferred embodiment, the medium comprises one or more compounds of formulas N, II, III, and T, preferably having a total concentration of 90% or higher, more preferably 95%, 96%, or 97% or higher, very preferably 98% or higher, and particularly 99% or higher.

[0831] In a preferred embodiment, the medium comprises one or more compounds of the formulas N, I, III, and T, preferably having a total concentration of 90% or higher, more preferably 95%, 96%, or 97% or higher, very preferably 98% or higher, and particularly 99% or higher.

[0832] More preferred embodiments of the present invention (alone or in combination with each other) are as follows, wherein some of the compounds are abbreviated using the acronyms given in Table C below:

[0833] - The medium comprises one, two, three, four or more compounds of formula III-1, preferably selected from formula III-1b, III-1f and III-1h; more preferably compounds of III-1b and III-1h;

[0834] - The medium contains a compound of formula III-1b, preferably in a total concentration of 5% to 35%, more preferably 10% to 30%, and particularly in the range of 15% to 25%;

[0835] - The medium contains a compound of formula III-1h, preferably in a total concentration of 10% to 40%, more preferably 15% to 35%, and particularly in the range of 18% to 30%;

[0836] -The medium contains compounds PPU-TO-S and / or PPTU-TO-S and / or PTPU-TO-S and / or PP(1)TO-nS;

[0837] - The medium contains one or more compounds of formula I-2d, preferably compounds PGU-2-S and / or PGU-3-S and / or PGU-4-S, and / or CPU-2-S and / or CPU-3-S and / or CPU-4-S;

[0838] - The medium contains one or more compounds of formula I-2d and formula II-1b, preferably compounds PGU-3-S and / or PGU-4-S and PTU-3-S and / or PTU-4-S and / or PTU-5-S;

[0839] - The medium contains one or more compounds of the form PPTU-nS and / or PTPU-nS, with a total concentration in the range of 15 to 25%;

[0840] - The medium contains one or more compounds of the formula PPTU-nS and / or PTPU-nS and / or PGTU-nS, with a total concentration in the range of 15% to 30%, wherein n is 1, 2, 3, 4, 5 or 6;

[0841] - The medium contains one or more compounds of the formula ST-3, preferably ST-3a and / or ST-3b, particularly preferably ST-3b-1, in a total concentration of 0.01 to 1%, preferably 0.05 to 0.5%, and especially in the range of 0.10 to 0.15%.

[0842] The liquid crystal medium according to the invention preferably has a clearing point of 90°C or higher, more preferably 100°C or higher, more preferably 110°C or higher, more preferably 120°C or higher, more preferably 130°C or higher, particularly preferably 140°C or higher, and very particularly preferably 150°C or higher.

[0843] The liquid crystal medium according to the invention preferably has a clearing point of 160°C or lower, more preferably 140°C or lower, particularly preferably 120°C or lower, and very particularly preferably 100°C or lower.

[0844] The nematic phase of the medium according to the invention preferably extends from at least 0°C or lower to 90°C or higher. Advantageously, the medium according to the invention exhibits an even wider range of nematic phases, preferably from at least -10°C or lower to 120°C or higher, very preferably from at least -20°C or lower to 140°C or higher, and particularly, from at least -30°C or lower to 150°C or higher, and very particularly preferably from at least -40°C or lower to 170°C or higher.

[0845] At 1 kHz and 20 °C, the Δε of the liquid crystal medium according to the present invention is preferably 5 or greater, more preferably 7 or greater, and very preferably 10 or greater.

[0846] At 589nm (Na D At 20°C, the birefringence (Δn) of the liquid crystal medium according to the invention is preferably 0.280 or greater, more preferably 0.300 or greater, even more preferably 0.320 or greater, very preferably 0.330 or greater, and especially 0.350 or greater.

[0847] At 589nm (Na D At 20°C, the preferred range of Δn for the liquid crystal medium according to the invention is 0.200 to 0.900, more preferably 0.250 to 0.800, even more preferably 0.300 to 0.700, and very particularly preferably 0.350 to 0.600.

[0848] In a preferred embodiment of this application, the Δn of the liquid crystal medium according to the present invention is preferably 0.50 or greater, more preferably 0.55 or greater.

[0849] The compounds of Formulas I to III each include, in each case, a dielectric positive compound having a dielectric anisotropy greater than 3, a dielectric neutral compound having a dielectric anisotropy less than 3 and greater than -1.5, and a dielectric negative compound having a dielectric anisotropy of -1.5 or less.

[0850] Compounds of formulas N, I, II and III are preferably dielectric positive.

[0851] In this application, dielectric positivity describes compounds or components where Δε > 3.0, dielectric neutrality describes those where -1.5 ≤ Δε ≤ 3.0, and dielectric negativity describes those where Δε < -1.5. Δε is measured at a frequency of 1 kHz and at 20 °C. The dielectric anisotropy of each compound is determined by the results of 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 mixture is measured in both cells with vertical alignment and cells with planar alignment. The cell thickness of both types of cells is approximately 20 μm. The applied voltage is a rectangular wave with a frequency of 1 kHz and an effective value typically between 0.5 V and 1.0 V, but it is always selected to be below the capacitance threshold of each test mixture.

[0852] Δε is defined as (ε||-ε ⊥ ), and ε ave . is (ε||+2ε ⊥ ) / 3.

[0853] The bulk mixture used to determine the physical constants of the pure compound by extrapolation was ZLI-4792 from Merck KGaA, Germany. The absolute values ​​of the dielectric constant, birefringence (Δn), and rotational viscosity (γ1) of the compound were measured by the changes in these values ​​of the bulk mixture after the addition of the compound. The concentration in the bulk was 10%, or 5% in cases of insufficient solubility. This value was extrapolated to 100% concentration of the added compound.

[0854] In the embodiments, the phase sequence of the pure compounds is given by the following abbreviations:

[0855] K: Crystalline, N: Nematic, SmA: Smectic A, SmB: Smectic B, I: Isotropic.

[0856] The nematic phase component was measured as is at a measurement temperature of 20°C, while all other components were treated similarly to the compound.

[0857] In both cases, unless otherwise expressly stated, the term "threshold voltage" used in this application refers to the optical threshold and is specific to a 10% relative contrast ratio (V). 10 The statement "saturation voltage" refers to optical saturation and is specific to 90% relative contrast (V). 90 The capacitive threshold voltage (V0), also known as the Freedericks threshold (V0), is used only when explicitly mentioned. Fr ).

[0858] Unless otherwise expressly stated, the parameter ranges specified in this application include limit values.

[0859] Different upper and lower limits indicated by different property ranges can be combined to obtain other preferred ranges.

[0860] Throughout this application, the following conditions and definitions apply unless otherwise stated. All concentrations are given as weight percentages and refer to their respective total mixtures; all temperature values ​​are given in Celsius and all temperature differences are given in differential degrees. All physical properties are determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals," Status November 1997, by Merck KGaA (Germany) and given for a temperature of 20°C, unless otherwise explicitly stated. Optical anisotropy (Δn) was determined at a wavelength of 589.3 nm. Dielectric anisotropy (Δε) was determined at a frequency of 1 kHz. Threshold voltage and all other electro-optic properties were determined using a test cell manufactured by Merck KGaA (Germany). The test cell used to determine Δε had a thickness of approximately 20 μm. The electrodes were 1.13 cm thick. 2 A circular ITO electrode with area and guard ring. For vertical orientation (ε||), the orientation layer is SE-1211 from Nissan Chemicals, Japan, and for surface orientation (ε||), the orientation layer is... ⊥ The orientation layer is polyimide AL-1054 from Japan Synthetic Rubber. A Solatron 1260 frequency response analyzer was used, employing a sine wave and 0.3V. rms The capacitance is measured by the voltage. White light is used in the electro-optic measurement. A DMS instrument, commercially available from Autronic-Melchers, Germany, is used. The characteristic voltage is measured under vertical observation. The threshold voltage (V) is measured at 10%, 50%, and 90% relative contrast. 10 ), medium gray voltage (V) 50 ) and saturation voltage (V 90 ).

[0861] As in A.Penirschke et al. "Cavity Perturbat ion Method for Characterization of Liquid Crystals up to 35GHz", 34 thThe study of liquid crystal media in terms of their performance in the microwave frequency range is described in the European Microwave Conference – Amsterdam, pp. 545-548. In this regard, comparisons are also made with A. Gaebler et al., “Direct Simulation of Material Permittivities…”, 12MTC 2009 – International Instrumentation and Measurement Technology Conference, Singapore, 2009 (IEEE), pp. 463-467 and DE 10 2004 029 429A, which also describe the measurement methods in detail.

[0862] Liquid crystal was introduced into a polytetrafluoroethylene (PTFE) or quartz capillary. The capillary had an inner diameter of 0.5 mm and an outer diameter of 0.78 mm. The effective length was 2.0 cm. The filled capillary was introduced into the center of a cylindrical cavity with a resonant frequency of 19 GHz. The cavity had a length of 11.5 mm and a radius of 6 mm. An input signal (source) was then applied, and the frequency-dependent response of the cavity was recorded using a commercial vector network analyzer (N5227APNA microwave network analyzer, Keysight Technologies Inc., USA). For other frequencies, the cavity dimensions were adapted accordingly.

[0863] The changes in resonant frequency and Q-factor between measurements using a capillary filled with liquid crystal and those using a capillary without liquid crystal were used to determine the dielectric constant and loss angle at the corresponding target frequency, as described in the aforementioned publication A. Penirschke et al., 34. th European Microwave Conference – Ams terdam, pp. 545-548, determinations of formulas 10 and 11 as described therein.

[0864] The values ​​of the components of the property perpendicular to and parallel to the liquid crystal director are obtained by the alignment of the liquid crystal in a magnetic field. For this purpose, a magnetic field of a permanent magnet is used. The magnetic field strength is 0.35 Tesla.

[0865] Preferred components include phase shifters, varactor diodes, wireless and radio wave antenna arrays, matching circuits, adaptive filters, and others.

[0866] In this application, the term "compound" means one compound and multiple compounds, unless otherwise expressly stated.

[0867] All mixtures according to the invention are nematic. The liquid crystal medium according to the invention preferably has a nematic phase within the preferred range given above. The statement "having a nematic phase" here means, on the one hand, that no smectic phase and no crystallization are observed at the corresponding temperature at low temperatures, and on the other hand, that no clearing occurs upon heating from the nematic phase. At high temperatures, the clearing point is measured in a capillary using conventional methods. Low-temperature studies are conducted using a flow viscometer at the corresponding temperature and examined by storing bulk samples: at a given temperature T, the storage stability (LTS) in the bulk of the medium according to the invention is determined by visual inspection. 2 g of the medium of interest is filled into a suitably sized sealed glass container (bottle) placed in a refrigerator at a predetermined temperature. The bottle is checked at defined time intervals for smectic phase formation or crystallization. Two bottles are stored for each material and at each temperature. If crystallization or a smectic phase is observed in at least one of the two corresponding bottles, the test is terminated, and the time of the last check before the observation of a higher ordered phase is recorded as the corresponding storage stability. Finally, the experiment was terminated after 1000 hours, meaning that an LTS value of 1000 hours indicates that the mixture is stable at a given temperature for at least 1000 hours.

[0868] The liquid crystal used preferably has positive dielectric anisotropy. This is preferably 2 or greater, more preferably 4 or greater, particularly preferably 6 or greater, and very particularly preferably 10 or greater.

[0869] Furthermore, the liquid crystal medium according to the present invention is characterized by high anisotropy values ​​in the microwave range. The birefringence at approximately 19 GHz is preferably 0.14 or higher, particularly preferably 0.15 or higher, particularly preferably 0.20 or higher, particularly preferably 0.25 or higher, and very particularly preferably 0.30 or higher. Additionally, the birefringence is preferably 0.80 or lower.

[0870] Dielectric anisotropy in the microwave range is defined as

[0871] △ε r ≡(ε r,|| -ε r,⊥ ).

[0872] Tunerness (τ) is defined as

[0873] τ≡(△ε r / ε r,|| ).

[0874] Material quality (η) is defined as

[0875] η≡(τ / tanδ εr,max. ),in

[0876] Maximum dielectric loss is

[0877] tanδε r,max。 ≡max.{tanδ εr,⊥, ;tanδ εr,||}

[0878] The tunability τ of the medium 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, and especially 0.350 or greater.

[0879] The preferred liquid crystal material has a material quality (η) of 6 or greater, preferably 8 or greater, preferably 10 or greater, preferably 15 or greater, preferably 17 or greater, preferably 20 or greater, particularly preferably 25 or greater, and very particularly preferably 30 or greater.

[0880] In the corresponding components, the phase shifter quality of the preferred liquid crystal material is 15° / dB or greater, preferably 20° / dB or greater, preferably 30° / dB or greater, preferably 40° / dB or greater, preferably 50° / dB or greater, particularly preferably 80° / dB or greater, and very particularly preferably 100° / dB or greater.

[0881] However, in some implementations, liquid crystals with negative dielectric anisotropy can also be advantageously used.

[0882] The liquid crystals used are either a single substance or a mixture. They preferably have a nematic phase.

[0883] The liquid crystal medium according to the invention may contain other additives and chiral dopants at typical concentrations. The total concentration of these other components, based on the entire mixture, is 0% to 10%, preferably 0.1% to 6%. The concentration of each individual compound used is preferably 0.1% to 3%. When referring to values ​​and concentration ranges of liquid crystal components and liquid crystal compounds in this application, these, as well as the concentrations of similar additives, are not taken into consideration.

[0884] Preferably, the medium according to the invention contains one or more chiral compounds as chiral dopants to adjust their cholesterol-type pitch. The total concentration of these compounds in the medium according to the invention is preferably in the range of 0.05% to 15%, more preferably 1% to 10%, and most preferably 2% to 6%.

[0885] Optionally, the medium according to the invention may contain other liquid crystal compounds to adjust physical properties. Such compounds are known to those skilled in the art. Their concentration in the medium according to the invention is preferably 0% to 30%, more preferably 0.1% to 20%, and most preferably 1% to 15%.

[0886] Specifically, the relative contrast for relative tuning or photoelectric response varies from 0% to 90% (t 90 The response time is the time of rise time (τ) (t0) on The value is given, including the delay time (t). 10 –t0); For relative tuning or photoelectric response, the relative contrast changes from 100% back to 10% (t 100 -t 10 The response time is the decay time (τ). off The total response time (τ) is given by τ. 总计 =τ on +τ off ).

[0887] The liquid crystal medium according to the invention comprises a variety of compounds, preferably 3-30, more preferably 4-20, and very preferably 4-16. These compounds are mixed in a conventional manner. Typically, a desired amount of compound used in a smaller quantity is dissolved in a larger quantity of compound used. The completion of the dissolution process is particularly easy to observe if the temperature is above the clearing point of the compound used at a higher concentration. However, the medium can also be prepared in other conventional ways, such as using so-called premixes, which can be, for example, homogeneous mixtures or eutectic mixtures of compounds, or using so-called "multi-bottle" systems, whose components are themselves ready-to-use mixtures.

[0888] All temperatures, such as melting point T(C, N) or T(C, S), the transition from smectic (S) phase to nematic (N) phase T(S, N), and the clearing point of liquid crystal T(N, I), are expressed in degrees Celsius. All temperature differences are expressed in degrees.

[0889] In this invention, and particularly in the following embodiments, the structure of the mesocrystalline compound is indicated by abbreviations, also known as acronyms. Among these acronyms, the chemical formulas are simplified using Tables A to D below. All groups C n H 2n+1 C m H 2m+1 and C l H 2l+1 and C n H 2n C m H 2m and C l H 2lThese represent straight-chain alkyl or alkylene groups having n, m, or l C atoms in each case, where n and m are independently 1, 2, 3, 4, 5, 6, or 7, and l is 1, 2, or 3. Table A lists the codes for the ring elements used in the core structure of the compounds, while Table B shows the linking groups. Table C gives the meaning of the codes for left-handed or right-handed end groups. Table D shows exemplary structures of the compounds and their respective abbreviations.

[0890] Table A: Ring Elements

[0891]

[0892]

[0893]

[0894]

[0895]

[0896]

[0897]

[0898] Table B: Connecting Bases

[0899]

[0900] Table B: End bases

[0901]

[0902]

[0903] Use in combination with other

[0904]

[0905] Where n and m each represent integers, and the three dots “…” are placeholders for other abbreviations in this table.

[0906] The table below shows exemplary structures and their respective abbreviations. These abbreviations are shown to illustrate the meaning of the abbreviation rules. They also represent compounds that are preferred for use.

[0907] Table C: Exemplary Structure

[0908] The following exemplary structures are compounds, which are preferably used in a medium:

[0909]

[0910]

[0911]

[0912]

[0913]

[0914]

[0915]

[0916]

[0917]

[0918]

[0919]

[0920]

[0921]

[0922]

[0923] Where m and n are the same or different and are 1, 2, 3, 4, 5, 6 or 7.

[0924] Preferably, the medium according to the invention comprises one or more compounds selected from Table C.

[0925] Table D below shows exemplary compounds that can be used as alternative stabilizers in mesocrystalline media according to the present invention. The total concentration of these and similar compounds in the media is preferably 5% or less.

[0926] Table D

[0927]

[0928]

[0929]

[0930] In a preferred embodiment of the invention, the mesocrystalline medium comprises one or more compounds selected from the group consisting of compounds in Table D.

[0931] Table E below shows exemplary compounds that can be preferably used as chiral dopants in mesocrystalline media according to the present invention.

[0932] Table E

[0933]

[0934]

[0935]

[0936] In a preferred embodiment of the invention, the mesocrystalline medium comprises one or more compounds selected from the group consisting of compounds listed in Table E.

[0937] The mesocrystalline medium according to this application preferably comprises two or more, more preferably four or more compounds selected from the group consisting of the compounds in the table above. Example

[0938] The following examples illustrate the present invention but do not limit the invention in any way.

[0939] Those skilled in the art will understand from the physical properties what properties can be realized and to what extent they can be modified. In particular, the preferred combinations of various achievable properties are therefore clearly defined to those skilled in the art.

[0940] Synthetic Examples Abbreviation:

[0941] RT (Room temperature) (20℃±1℃)

[0942] THF tetrahydrofuran

[0943] MTB ether methyl tert-butyl ether

[0944] di s t. distillation

[0945] XPhos 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl XPhos Pd G2-chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)palladium(II)]

[0946] Example 1: 2-[4-(4-butylcyclohexyl)phenyl]-5-isothiocyanate-pyrimidine

[0947] Step 1.1: 2-[4-(4-butylcyclohexyl)phenyl]pyrimidine-5-amine

[0948]

[0949] A mixture of [4-(4-butylcyclohexyl)phenyl]boronic acid (CAS No. 516510-90-0) (5.1 g, 19.7 mmol), 2-bromopyrimidine-5-amine (CAS No. 1072-97-5) (3.0 g, 16.4 mmol), and potassium carbonate (6.8 g, 49.1 mmol) in ethanol (7.6 ml), distilled water (7.6 ml), and toluene (25.4 ml) was treated with bis(triphenylphosphine)palladium(II) dichloride (345 mg) and heated to reflux and stirred overnight at reflux under an argon atmosphere. The mixture was cooled to RT and concentrated under vacuum. The residue was purified by silica gel chromatography (dichloromethane and ethyl acetate) to give 2-[4-(4-butylcyclohexyl)phenyl]pyrimidine-5-amine as a colorless solid.

[0950] Step 1.2: 2-[4-(4-butylcyclohexyl)phenyl]-5-isothiocyanate-pyrimidine

[0951]

[0952] A solution of 2-[4-(4-butylcyclohexyl)phenyl]pyrimidin-5-amine (6.1 g, 19.7 mmol) and DABCO (5.5 g, 49.3 mmol) in dichloromethane (75 mL) was cooled to 0 °C, and phosgene (2.1 mL, 27.4 mmol) was added dropwise using a syringe. The suspension was stirred at RT for 1 hour. The reaction mixture was then hydrolyzed with distilled water and brine. The mixture was stirred for 5 minutes, and the aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried (sodium sulfate), and concentrated under vacuum. The residue was purified by silica gel chromatography (n-heptane and toluene) and crystallization (n-heptane) to give 2-[4-(4-butylcyclohexyl)phenyl]-5-isothiocyanate-pyrimidinium as a colorless solid.

[0953] Phase sequence: K 128I.

[0954] Δε=3.72

[0955] Δn=0.3113

[0956] γ1=463mPas

[0957] Example 2: 2-[4-(4-butylcyclohexyl)phenyl]-3-chloro-5-isothiocyanate-pyridine

[0958] Step 2.1: 6-[4-(4-butylcyclohexyl)phenyl]-5-chloro-pyridine-3-amine

[0959]

[0960] A mixture of [4-(4-butylcyclohexyl)phenyl]boronic acid (CAS No. 516510-90-0) (4.33 g, 16.5 mmol), 6-bromo-5-chloro-3-pyridinamine (CAS No. 130284-52-5) (3.5 g, 16.5 mmol), and potassium carbonate (4.6 g, 33.3 mmol) in dioxane (60 ml) and distilled water (15 ml) was treated with bis(triphenylphosphine)-palladium(II) dichloride (710 mg) and heated to reflux and stirred overnight at reflux temperature under an argon atmosphere. The mixture was then cooled to RT and concentrated under vacuum. The residue was purified by silica gel chromatography (dichloromethane and ethyl acetate) to give 6-[4-(4-butylcyclohexyl)phenyl]-5-chloro-pyridin-3-amine as a colorless solid.

[0961] Step 2.2: 2-[4-(4-butylcyclohexyl)phenyl]-3-chloro-5-isothiocyanate-pyridine

[0962]

[0963] A solution of 6-[4-(4-butylcyclohexyl)phenyl]-5-chloro-pyridine-3-amine (9) (5.3 g, 15.4 mmol) and DABCO (4.4 g, 39.2 mmol) in dichloromethane (100 ml) was cooled to 0 °C, and phosgene (1.50 ml, 18.9 mmol) was added dropwise by syringe. The suspension was stirred at RT for 1 hour. The reaction mixture was then hydrolyzed with distilled water and brine. The mixture was stirred for 5 minutes, and the aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried (sodium sulfate), and concentrated under vacuum. The residue was purified by silica gel chromatography (n-heptane and toluene) and crystallization (n-heptane). 2-[4-(4-butylcyclohexyl)phenyl]-3-chloro-5-isothiocyanate-pyridine (10) was separated as a colorless solid.

[0964] Phase sequence: K 69N 112.9II.

[0965] Δε=1.99

[0966] Δn = 0.2351

[0967] Example 3: 2-[4-(4-butylcyclohexyl)phenyl]-5-isothiocyanate-pyridine

[0968] Step 3.1: 6-[4-(4-butylcyclohexyl)phenyl]pyridine-3-amine

[0969]

[0970] A mixture of [4-(4-butylcyclohexyl)phenyl]boronic acid (CAS No. 516510-90-0) (4.5 g, 17.3 mmol), 2-bromopyridin-5-amine (CAS No. 13534-97-9) (3.0 g, 16.8 mmol), potassium carbonate (4.7 g, 34 mmol) in dioxane (60 ml) and distilled water (15 ml) was treated with bis(triphenylphosphine)-palladium(II) dichloride (710 mg) and heated to reflux and stirred overnight at reflux under an argon atmosphere. The mixture was cooled to RT and concentrated under vacuum. The residue was purified by silica gel chromatography (dichloromethane and ethyl acetate) to give 6-[4-(4-butylcyclohexyl)phenyl]pyridin-3-amine as a colorless solid.

[0971] Step 3.2: 2-[4-(4-butylcyclohexyl)phenyl]-5-isothiocyanate-pyridine

[0972]

[0973] A solution of 6-[4-(4-butylcyclohexyl)phenyl]pyridine-3-amine (4.5 g, 14.4 mmol) and DABCO (4.1 g, 36.5 mmol) in dichloromethane (50 mL) was cooled to 0 °C, and phosgene (1.4 mL, 17.7 mmol) was added dropwise using a syringe. The suspension was stirred at RT for 1 hour and hydrolyzed with distilled water and brine. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried (sodium sulfate), and concentrated under vacuum. The residue was purified by silica gel chromatography (n-heptane and toluene) and crystallization (n-heptane) to give 2-[4-(4-butylcyclohexyl)phenyl]-5-isothiocyanate-pyridine as a colorless solid.

[0974] Phase sequence: K 73SmA 207N 247.4I

[0975] Δε=5.42

[0976] Δn = 0.3209

[0977] γ1=594mPas

[0978] Example 4: 6-[4-(4-butylcyclohexyl)phenyl]-2-chloro-3-isothiocyanate-pyridine Step 4.1: 6-[4-(4-butylcyclohexyl)phenyl]-2-chloro-pyridine-3-amine

[0979]

[0980] A mixture of [4-(4-butylcyclohexyl)phenyl]boronic acid (CAS No. 516510-90-0) (4.3 g, 16.5 mmol), 6-bromo-2-chloro-3-pyridinamine (CAS No. 169833-70-9) (3.5 g, 16.5 mmol), potassium carbonate (4.6 g, 33 mmol), and dioxane (60 ml) in 15 ml distilled water was treated with bis(triphenylphosphine)-palladium(II) dichloride (700 mg) and heated to reflux and stirred overnight at reflux temperature under an argon atmosphere. The mixture was then cooled to RT and concentrated under vacuum. The residue was purified by silica gel chromatography (dichloromethane and ethyl acetate) to give 6-[4-(4-butylcyclohexyl)phenyl]-2-chloro-pyridin-3-amine as a colorless solid.

[0981] Step 4.2: 6-[4-(4-butylcyclohexyl)phenyl]-2-chloro-3-isothiocyanate-pyridine

[0982]

[0983] A solution of 6-[4-(4-butylcyclohexyl)phenyl]-2-chloro-pyridin-3-amine (4.3 g, 12.5 mmol) and DABCO (3.6 g, 32 mmol) in dichloromethane (100 ml) was cooled to 0 °C, and phosgene (2.1 ml, 27.4 mmol) was added dropwise using a syringe. The suspension was stirred at RT for 1 hour. The reaction mixture was then hydrolyzed with distilled water and brine. The mixture was stirred for 5 minutes, and the aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried (sodium sulfate), and concentrated under vacuum. The residue was purified by silica gel chromatography (n-heptane and toluene) and crystallization (n-heptane) to give 6-[4-(4-butylcyclohexyl)phenyl]-2-chloro-3-isothiocyanate-pyridine as a colorless solid.

[0984] Phase sequence: K 105SmA(81)N 171.3I.

[0985] Δε=5.52

[0986] Δn = 0.2989

[0987] Similar to the synthesis examples 1 to 4, the following compounds were obtained.

[0988]

[0989]

[0990]

[0991]

[0992]

[0993]

[0994]

[0995]

[0996]

[0997]

[0998]

[0999]

[1000]

[1001]

[1002] Mixture Examples

[1003] Liquid crystal mixtures H1 to H3 and M1 to M9 having the composition and properties indicated in the table below were prepared and characterized relative to their general physical properties at 19 GHz and 20 °C and their suitability in microwave components.

[1004] Main mixture H1

[1005]

[1006] Main mixture H2

[1007]

[1008] Main mixture H3

[1009]

[1010]

[1011] Main mixture H4

[1012]

[1013]

[1014] Mixture Example M1

[1015]

[1016] Adding the compound CPMI-4-S according to the present invention to dielectric H1 results in a higher adjustable quality factor η and a lower dielectric loss tanδ. εr,⊥ It was improved from 8.0 to 9.6.

[1017] Mixture Example M2

[1018]

[1019]

[1020] Compared to the main mixture H2, the medium M2 has a significantly improved clearing temperature due to the presence of the compound CPNI-4-S according to the invention.

[1021] Mixture Example M3

[1022]

[1023] Adding the compound CPNI(5Cl)-4-S according to the invention to the dielectric H2 resulted in an increase in the quality factor η from 29.3 to 31.4 due to lower dielectric loss tanδ.

[1024] Mixture Example M4

[1025]

[1026] The compound CPNI(2Cl)-4-S is highly suitable for use in the media according to the present invention due to its advantageous application properties.

[1027] Mixture Example M5

[1028]

[1029] Dielectric M5 has a significantly lower dielectric loss than the host dielectric H3 alone, while the quality factor remains almost unchanged.

[1030] Mixture Example M6

[1031]

[1032] As shown in medium M6, the effect exhibited in medium M5 is further improved when the concentration of the compound of formula CPMI-4-S according to the invention is increased from 5% to 10%.

[1033] Mixture Example M7

[1034]

[1035] Due to the presence of the compound CPNI(5Cl)-4-S according to the invention, mixture example M7 has an extremely high quality factor η due to its high tunability and, in particular, extremely low dielectric loss.

[1036] Mixture Example M8

[1037]

[1038]

[1039] Due to the presence of the compound CPNI(5Cl)-4-S according to the invention, mixture example M8 has an extremely high quality factor η due to its high tunability and, in particular, extremely low dielectric loss.

[1040] Mixture Example M9

[1041]

[1042] Adding the compound according to the invention to the host medium H4 results in an improved quality factor due to lower dielectric loss.

Claims

1. A compound selected from compounds of formula N-1 to N-3. in R N The symbol represents H, an alkyl or alkoxy group each having 1 to 12 carbon atoms, or an alkenyl, alkenyloxy, or alkoxyalkyl group each having 2 to 12 carbon atoms, wherein one or more CH2 groups may be derived from H. Substitution, or indicating group R P , R P Indicates halogen, CN, NCS, R F R F -O- or R F -S-, where R F This indicates a fluorinated alkyl group having 1 to 9 carbon atoms or a fluorinated alkenyl group having 2 to 9 carbon atoms. Y 1 and Y 2 Same or different, indicating H, F, Cl or CH3, and t is 0 or 1, and Representing each other independently in Or indicate and L 1 and L 2 Same or different, indicating H, F, Cl, or an alkyl group having 1 to 12 carbon atoms, or an alkenyl group having 2 to 12 carbon atoms, or a branched or cyclic alkyl or alkenyl group each having 3 to 12 carbon atoms. Z N1 and Z N2 Same or different indicates -C≡C- or a single bond.

2. The compound according to claim 1, wherein the compound is selected from the group consisting of formulas N-1-1 to N-1-7, N-1-9 to N-1-12 and N-2-1 to N-2-7, N-2-9 to N-2-12. Where L 1 and L 2 Same or different, indicating H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclopentenyl, and R N Y 1 and Y 2 It has the meaning given in claim 1.

3. The compound according to claim 1 or 2, wherein Y 1 and Y 2 One or both of them represent H.

4. The compound according to claim 1 or 2, wherein R N This indicates an alkyl group having 1 to 12 carbon atoms.

5. The compound according to claim 1 or 2, wherein the group R N R as defined in claim 1 P .

6. A liquid crystal medium comprising one or more compounds according to any one of claims 1 to 5.

7. The liquid crystal medium of claim 6, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulas I, II, and III. in R 1 The expression represents H, an unfluorinated alkyl or unfluorinated alkoxy group having 1 to 17 carbon atoms, or an unfluorinated alkenyl, unfluorinated alkenyloxy, or unfluorinated alkoxyalkyl group having 2 to 15 carbon atoms, wherein one or more CH2 groups may be derived from H. Replacement n is 0, 1, or 2. to Each time it appears, it represents independently of each other. Where R L The fact that the same or different occurrences indicate H or have Alkyl groups with 1 to 6 carbon atoms And among them Or indicate R 2 The expression represents H, an unfluorinated alkyl or unfluorinated alkoxy group having 1 to 17 carbon atoms, or an unfluorinated alkenyl, unfluorinated alkenyloxy, or unfluorinated alkoxyalkyl group having 2 to 15 carbon atoms, wherein one or more CH2 groups may be derived from H. Replacement Z 21 This indicates the trans form -CH = CH-, the trans form -CF = CF-, or -C ≡ C-, and and Independently representing Where R L The same or different occurrences each time indicate H or having Alkyl groups having 1 to 6 carbon atoms; R 3 The expression represents H, an unfluorinated alkyl or unfluorinated alkoxy group having 1 to 17 carbon atoms, or an unfluorinated alkenyl, unfluorinated alkenyloxy, or unfluorinated alkoxyalkyl group having 2 to 15 carbon atoms, wherein one or more CH2 groups may be derived from H. Replacement Z 31 and Z 32 One of them 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 to Independently representing Where R L The same or different occurrences each time indicate H or Alkyl groups having 1 to 6 carbon atoms And among them Or indicate 8. The liquid crystal medium according to claim 6 or 7, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulas I-1 to I-5. in L 1 L 2 and L 3 The same or different occurrences each time indicate H or F, and R 1 , and It has the meaning given for formula I in claim 7.

9. The liquid crystal medium according to claim 6 or 7, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulas II-1 to II-3. Where R 2 , and It has the meaning given in claim 7 for formula II.

10. The liquid crystal medium according to claim 6 or 7, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulas III-1 to III-6. in R 3 , and It has the meaning given in claim 7 for formula III, and Z 31 and Z 32 They represent the trans-CH=CH- or trans-CF=CF- independently, and in Equation III-6, Z 31 and Z 32 One of them is represented as -C≡C-.

11. The liquid crystal medium according to claim 6 or 7, wherein the medium comprises one or more compounds of formula T. in R T Indicates halogen, CN, NCS, R F R F -O- or R F -S-, where R F It indicates a fluorinated alkyl or fluorinated alkenyl group having up to 12 carbon atoms. and Each time it appears, it represents independently of each other. L 4 and L 5 Same or different, indicating F, Cl or straight-chain or branched or cyclic alkyl or alkenyl groups each having up to 12 C atoms; Z T3 Z T4 Same or different indicates -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C- or a single bond, and t is 0 or 1.

12. A component for high-frequency technology, characterized in that it comprises a liquid crystal medium according to any one of claims 6 to 11.

13. The component of claim 12, wherein the component is a liquid crystal-based antenna element, a phase shifter, a tunable filter, a tunable metamaterial structure, a matching network, or a varactor diode.

14. A microwave antenna array, characterized in that... It contains one or more components according to claim 12 or 13.

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