Optical assembly

Abstract

This invention relates to optical components comprising liquid crystal (LC) media that can operate in the infrared region of the electromagnetic spectrum. The invention also relates to the use of said LC media in the infrared (IR) region and devices comprising said optical components. Furthermore, the invention relates to LC media comprising one or more compounds of formulas I, II, and III, wherein the groups and parameters therein have the meaning as defined in claim 1, and preferably comprises one or more compounds of formula RO, wherein the groups and parameters therein have the meaning as defined in claim 2.

Description

[0001] This invention relates to optical components comprising a liquid crystal (LC) medium, which can operate in the infrared region of the electromagnetic spectrum. The invention also relates to the use of said LC medium in the infrared (IR) region and devices comprising said optical components.

[0002] Liquid crystal media have been used in electro-optical displays (LCDs) for many years to display information by modulating the amplitude of polarized light in the visible light region. Nematic liquid crystals have also been proposed for phase modulation of light: the article Mcmanamon PF, Dorschner TA, Corkum DL, Friedman LJ, Hobbs DS, Holz M, Liberman S, Nguyen HQ, Resler DP, Sharp RC, Watson EA. Optical phased array technology. Proc IEEE. 1996; 84:268–298. doi:10.1109 / 5.482231 describes liquid crystal-based optical phased arrays for various types of sensor applications; the article Scott R. Davis, George Farca, Scott D. Rommel, Seth Johnson, Michael H. Anderson, "Liquid crystal waveguides: new devices enabled by >1000 waves of optical phase control," Proc. SPIE 7618, Emerging Liquid Crystal Technologies V, 76180E (February 12) (2010); doi:10.1117 / 12.851788 describes the manipulation of refracted beams using waveguide structures.

[0003] Telecommunications increasingly requires optical components that operate in the infrared range. For example, wavelength-selective switching (WSS)-based reconfigurable optical add-drop multiplexers (ROADMs) are a crucial component of dynamic optical networks. The rapidly growing demand for high-speed broadband communications has led to the development of so-called colorless, directionless, contentless, and meshless (CDC-F) network architectures. The wavelength-selective switching technology upon which the latest generation of ROADMs is based is envisioned to provide the CDC-F capabilities upon which next-generation optical networks rely. Currently, several competing switching engine technologies are used in WSSs, one of which is the liquid crystal on silicon (LCoS) spatial light modulator (SLM). The advantages of LCoS-SLMs include flexible bandwidth adjustment, adaptive optical alignment for high port count WSSs, and stability without mechanical movement.

[0004] Another application of liquid crystal-based devices is light detection and ranging (Lidar), a method of measuring distance by illuminating a target with a laser and measuring the reflection using a sensor. The difference between the laser return time and wavelength can be used to create a digital 3D representation of the target. A holographic Lidar system using, for example, an LCoS SLM is proposed in WO2019 / 24052A1.

[0005] US10,665,953B1 proposes a tunable optical metasurface comprising an optical reflective surface for reflecting infrared laser light, wherein an array of optical resonant antennas located on the reflective surface and a pressure-controlled liquid crystal is situated in the optical field region of each optical resonant antenna to enable one-dimensional beam control or shaping of a LiDAR system.

[0006] One of the most important characteristics of pure-phase LCoS devices is their use of optically nonlinear liquid crystal (LC) materials that are sensitive to operating temperature. While the main focus of LCoS devices in the past was on light intensity modulation, which is minimally affected by temperature changes, for pure-phase LCoS devices, the optical phase modulation of the incident light is an important performance parameter. It is easily affected by small changes in operating temperature, leading to significant changes in the corresponding optical diffraction results.

[0007] Known liquid crystal mixtures optimized for conventional display applications such as TVs or mobile phones are unsuitable for infrared applications because their birefringence decreases with increasing wavelength, requiring optics with extremely high cell gaps for modulating IR radiation. Many liquid crystal mixtures suffer from insufficient birefringence (Δn) and high optical loss in the infrared region. The article Fenglin Peng, Yuan Chen, Shin-Tson Wu, Suvagata Tripathi & Robert J. Twieg (2014) Low loss liquid crystals for infrared applications, LiquidCrystals, 41:11, 1545-1552, DOI:10.1080 / 02678292.2014.932452 proposes avoiding liquid crystal mixture components with CN or NCS polar groups, instead using chlorine or fluorine. This problem is particularly acute for devices requiring phase modulation at NIR wavelengths. Mixtures optimized solely for birefringence are insufficient for commercial applications; other thermal, optical, and electro-optic properties are also important. For outdoor infrared applications of liquid crystal attenuators, a wide temperature range and low-temperature dependence of optical characteristics with temperature are typically required.

[0008] A key challenge in developing next-generation LCoS devices is creating high-speed, multi-level phase modulation. Nematic LCoS devices have demonstrated the advantages of multi-level phase modulation, but are limited by the slow response time of nematic LCs. This is particularly true in telecommunications applications, where the infrared wavelengths used require thicker devices, further slowing the response time. Therefore, a major materials challenge for these applications is finding a suitable high-speed LC material that can provide the full 2π phase depth required for these applications.

[0009] It requires liquid crystal-based optical components that can operate in the infrared region of the electromagnetic spectrum, have improved overall application-related properties, and feature high birefringence and fast switching speed.

[0010] This invention was designed in response to the problems of the prior art described herein. Therefore, the overall objective of this invention is to provide novel and useful devices and techniques capable of solving the problems described herein.

[0011] The object of the present invention is an optical assembly comprising a liquid crystal medium sandwiched between a pair of substrates, wherein the liquid crystal medium comprises one or more compounds of formulas I, II, and III.

[0012]

[0013] in

[0014] R 1 The expression represents H, a straight-chain or branched alkyl group having 1 to 12, preferably 2 to 7, carbon atoms, or an alkenyl group having 2 to 15, preferably 2 to 7, carbon atoms, wherein one or more CH2- groups may be... Alternatives, preferably alkyl or alkenyl,

[0015] n is 0, 1, or 2.

[0016] to Each occurrence is represented independently.

[0017]

[0018] Where R L The H or an alkyl group having 1 to 6 carbon atoms is represented in the same or different ways each time it appears, preferably H, methyl or ethyl, particularly H, and wherein

[0019] Alternative representation

[0020]

[0021] Preferably representing

[0022] And when n=2, One of the preferred representations And another preferred representation

[0023]

[0024] Preferably

[0025] to Representing each other independently

[0026]

[0027] More preferably

[0028] express

[0029] express

[0030] express

[0031] R 2 The expression represents H, a straight-chain or branched alkyl group having 1 to 12, preferably 2 to 7, carbon atoms, or an alkenyl group having 2 to 15, preferably 2 to 7, carbon atoms, wherein one or more CH2- groups may be... Alternatives, preferably alkyl or alkenyl,

[0032] Z 21 This indicates the trans form -CH = CH-, the trans form -CF = CF-, or -C ≡ C-, preferably -C ≡ C-, and

[0033] and Representing each other independently

[0034]

[0035] Where R L The H or an alkyl group having 1 to 6 carbon atoms is represented in the same or different ways each time it appears, preferably H, methyl or ethyl, particularly H, and wherein

[0036] Preferably

[0037] and Representing each other independently

[0038]

[0039] Preferably representing and

[0040] Preferably representing

[0041] More preferably,

[0042] R 3 The expression represents H, a straight-chain or branched alkyl group having 1 to 12, preferably 2 to 7, carbon atoms, or an alkenyl group having 2 to 15, preferably 2 to 7, carbon atoms, wherein one or more CH2- groups may be... Alternatives, preferably alkyl or alkenyl,

[0043] Z 31 and Z 32 One of the preferred choices is Z. 32 This indicates the trans-CH=CH-, trans-CF=CF-, or -C≡C-, and another independent of it indicates -C≡C-, trans-CH=CH-, trans-CF=CF-, or a single bond, preferably one of them, preferably Z. 32 This indicates -C≡C- or trans-CH=CH-, and the other indicates a single bond.

[0044] to Representing each other independently

[0045]

[0046] Where R L The H or an alkyl group having 1 to 6 carbon atoms is represented in the same or different ways each time it appears, preferably H, methyl or ethyl, particularly H, and wherein Alternative representation

[0047]

[0048] Preferably,

[0049] to Representing each other independently

[0050]

[0051] More preferably

[0052]

[0053] express

[0054]

[0055] express

[0056] in particular

[0057] express

[0058] in particular

[0059] Compounds of formula RO are excluded from compounds of formulas I, II and III.

[0060] In compounds of formulas I, II, and III, R L H is the preferred option.

[0061] In another preferred embodiment, in the compounds of formulas I, II, and III, one or both R groups L Preferably, one group R L Unlike H.

[0062] The present invention also relates to the use of a context-defined medium in the infrared region of the electromagnetic spectrum, preferably in the A-band, and / or B-band and / or C-band, for phase modulation of said infrared light.

[0063] The present invention also relates to devices incorporating optical components according to the invention. Preferred devices are infrared imagers, wavelength-selective switches, LCoS-SLMs, LiDAR systems, wavelength division multiplexing (WDM) systems, reconfigurable optical add-drop multiplexers (ROADMs), and nonmechanical beam control, such as the controllable electroevanescent optical refraction (SEEOR) prism published in P. McManamon, 2006, "Agile Nonmechanical BeamSteering," Opt. Photon. News 17(3):24-29.

[0064] According to another aspect of the present invention, a method for spatially modulating infrared light is provided, the method comprising:

[0065] i) Provide an optical assembly comprising first and second substrates facing each other and each having a surface, the first substrate comprising at least one first electrode, the second substrate comprising at least one second electrode, the assembly further comprising a liquid crystal layer sandwiched between the first and second substrates, wherein the liquid crystal comprises one or more compounds selected from compounds of formulas I, II and III above;

[0066] ii) Receive incident infrared light on the surface of the optical component;

[0067] iii) Apply a predetermined voltage to each electrode formed on the first substrate to modulate the refractive index of the liquid crystal layer.

[0068] According to another aspect of the present invention, a method for manufacturing an optical phase modulator is provided, comprising at least the following steps:

[0069] a) Provide a first substrate having a first electrode, the first electrode optionally having a two-dimensional array of individually electrically drivable units;

[0070] b) Deposit a liquid crystal medium as described in this invention on the first substrate;

[0071] and

[0072] c) Mount a second substrate having a second electrode onto the liquid crystal material.

[0073] The optical component according to the invention is characterized by excellent operational stability when exposed to the environment due to the high brightness temperature, wide nematic phase range, and excellent low-temperature stability (LTS) of the liquid crystal medium used therein. As a result, the component and devices comprising it can operate under extreme temperature conditions. Surprisingly, the temperature dependence of the birefringence of the liquid crystal medium is very small, i.e., Δn changes very little with temperature, which makes the device reliable and easy to control.

[0074] The dielectric used in the components according to the invention is characterized by high dielectric anisotropy and low rotational viscosity. As a result, the threshold voltage, i.e., the minimum voltage at which the device can be switched, is very low. To achieve improved switching characteristics and high energy efficiency, both low operating voltage and low threshold voltage are required. The low rotational viscosity enables rapid switching of the components and devices according to the invention.

[0075] As used in this article, the infrared region of the electromagnetic spectrum refers to the spectral region of electromagnetic radiation with wavelengths ranging from 0.75 μm to 1000 μm.

[0076] As used in this article, infrared A (IR-A) refers to the spectral region of electromagnetic radiation with wavelengths ranging from 0.75 μm to 1.4 μm.

[0077] As used in this article, infrared B (IR-B) refers to the spectral region of electromagnetic radiation with wavelengths ranging from 1.4 μm to 3 μm.

[0078] As used in this article, infrared C (IR-C) refers to the spectral region of electromagnetic radiation with wavelengths ranging from 3 μm to 1000 μm.

[0079] Preferably, the optical components according to the invention operate in the wavelength range of 750 nm to 2500 nm, particularly 1530 nm to 1565 nm.

[0080] A highly preferred light source for use in the application according to the invention is an IR laser that emits light with a wavelength of 1.55 μm or an IR laser that emits light with a wavelength of 905 nm.

[0081] As used herein, the halogen is F, Cl, Br or I, preferably F or Cl, and particularly preferably F.

[0082] In this document, the alkyl group is straight-chain or branched and has 1 to 15 carbon atoms, preferably straight-chain, and unless otherwise stated, has 1, 2, 3, 4, 5, 6 or 7 carbon atoms, and is therefore preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0083] In this document, branched alkyl groups are alkyl groups having secondary and / or tertiary carbon atoms, preferably secondary carbon atoms, and are preferably isopropyl, s-butyl, isobutyl, isopentyl, 2-methylhexyl or 2-ethylhexyl, 2-methylpropyl, 2-pentyl, 3-pentyl, 2-methylbutyl, 3-methylbutyl.

[0084] In this document, cycloalkyl refers to a cycloaliphatic group or an alkyl group in which the methylene group is replaced by a cycloaliphatic group (i.e., cycloalkylalkyl or alkylcycloalkylalkyl), which may be saturated or partially unsaturated, and preferably represents cyclopropyl, methylcyclopropyl, cyclobutyl, methylcyclobutyl, cyclopentyl, methylcyclopentyl, cyclopentyl-1-enyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclopentyl-1-enylmethyl.

[0085] 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 stated, has 1, 2, 3, 4, 5, 6 or 7 carbon atoms, and therefore preferably methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy.

[0086] In this document, 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, vinyl, propenyl or propenyl-2-alkenyl, butenyl, butenyl or butenyl-3-alkenyl, pentenyl, pentenyl, pentenyl-2-alkenyl, pentenyl-3-alkenyl or pentenyl-4-alkenyl, hexenyl, hexenyl-2-alkenyl, hexenyl-3-alkenyl, hexenyl-4-alkenyl or hexenyl-5-alkenyl, heptenyl, heptenyl-2-alkenyl, heptenyl-3-alkenyl, heptenyl-4-alkenyl, heptenyl-5-alkenyl or heptenyl-6-alkenyl are preferred. If the two carbon atoms of the C-C double bond are substituted, the alkenyl group can 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-enyl, and but-3-enyl, as well as pent-3-enyl and pent-4-enyl, are particularly preferred.

[0087] 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. Preferred are 1-propynyl and 2-propynyl and 1-butynyl, 2-butynyl and 3-butynyl.

[0088] If R F The term "halogenated alkyl," "halogenated alkoxy," "halogenated alkenyl," or "halogenated alkenyloxy" can be branched or unbranched. Preferably, it is unbranched, mono-, poly-, or perfluorinated, and more preferably perfluorinated, and has 1, 2, 3, 4, 5, 6, or 7 carbon atoms if the alkenyl group has 2, 3, 4, 5, 6, or 7 carbon atoms.

[0089] R P Preferably, it represents CN, NCS, Cl, F, or -(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.

[0090] Preferably, the medium comprises one or more compounds of the formula RO.

[0091]

[0092] in

[0093] R RO This refers to a straight-chain or branched alkyl group having 1 to 12 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups in each group may be... Replacement

[0094] Z T1 Z T2 The same or different representations can be -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, or a single bond, preferably -CF=CF-, -C≡C-, or a single bond.

[0095] X 1 X 2 X 3 and X 4 The same or different representations of H, Cl, F or CH3, preferably H or F,

[0096] t is 0 or 1, and

[0097] and Groups selected from the following groups:

[0098] a) The group consisting of 1,4-phenylene, 1,4-naphthylene, and 2,6-naphthylene, wherein one or both CH groups may be substituted with N, and one or more H atoms may be substituted with L.

[0099] b) The group consisting of thiophene-2,5-diyl, thiophene[3,2-b]thiophene-2,5-diyl, selenophene-2,5-diyl, and furan-2,5-diyl, each optionally mono- or poly-substituted by L.

[0100] L, in each instance, may refer to F, Cl, or a straight or branched alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy, or alkoxy carbonyloxy group having 1 to 12 carbon atoms, optionally fluorinated in each case.

[0101] In a preferred embodiment, R in formula RO RO It indicates a straight-chain alkyl or alkenyl group having up to 7 carbon atoms.

[0102] In another preferred embodiment, R in formula RO RO It indicates a branched alkyl or alkenyl group having up to 10 carbon atoms.

[0103] In another preferred embodiment, R in formula RO RO This indicates a cycloalkyl group having up to 10 carbon atoms.

[0104] Preferably, the compound of formula RO is selected from formulas RO-1 to RO-7.

[0105]

[0106] Where X 1 and X 2 It can be represented by H, Cl, F or CH3, with H or F preferred.

[0107] and It has the above meaning, and

[0108] Preferably representing

[0109]

[0110] Very preferably means

[0111] R RO Having one of the above meanings, and preferably representing methyl, ethyl, n-propyl, 2-propyl, n-butyl, 2-butyl, 2-methylpropyl, n-pentyl, 2-pentyl, 3-pentyl, 2-methylbutyl, 3-methylbutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentyl-1-enyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentyl, cyclopentyl-1-enylmethyl, wherein one or more, but not all, of the H atoms can be substituted by F.

[0112] More preferred compounds of formulas RO-1 to RO-7 are selected from formulas RO-2, RO-3, RO4 and RO-5, with RO-2 being the most preferred;

[0113] Particularly preferably, the medium comprises one or more n-alkoxy derivatives of formula RO-2 selected from formulas RO-2-1a to RO-2-1l and / or one or more branched alkoxy derivatives of formula RO-2 selected from formulas RO-2-2a to RO-2-2m and / or one or more cycloalkoxy derivatives of formula RO-2 selected from formulas RO-2-3a to RO-2-3p.

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] In a preferred embodiment of the present invention, the compound of formula I is selected from the compounds of formulas I-1 to I-5:

[0121]

[0122] in

[0123] L 1 L 2 and L 3 Each occurrence may represent H or F in the same or different ways.

[0124] And other groups have the corresponding meanings shown in Formula I above, and

[0125] Preferably

[0126] R 1 It indicates an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

[0127] The medium preferably comprises one or more compounds of formula I-1, preferably selected from formulas I-1a to I-1d, and preferably compounds of formula I-1b:

[0128]

[0129] Where R 1 It has the meaning shown in Formula I above, and preferably represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

[0130] The medium preferably comprises one or more compounds of formula I-2, preferably selected from formulas I-2a to I-2e, and preferably compounds of formula I-2c:

[0131]

[0132]

[0133] Where R 1Having the meaning shown in Formula I above, it preferably represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

[0134] The medium preferably comprises one or more compounds of formula I-3, preferably selected from formulas I-3a to I-3d, and particularly preferably compounds of formula I-3b:

[0135]

[0136] Where R 1 Having the meaning shown in Formula I above, it preferably represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

[0137] The medium preferably comprises one or more compounds of formula I-4, preferably selected from formulas I-4a to I-4e, and particularly preferably compounds of formula I-4b:

[0138]

[0139] Where R 1 Having the meaning shown in Formula I above, it preferably represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

[0140] The medium preferably comprises one or more compounds of formula I-5, preferably selected from formulas I-5a to I-5d, and particularly preferably compounds of formula I-5b:

[0141]

[0142]

[0143] Where R 1 Having the meaning shown in Formula I above, it preferably represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

[0144] The medium preferably comprises one or more compounds of formula II, preferably selected from compounds of formulas II-1 to II-3, and very preferably selected from compounds of formulas II-1 and II-2:

[0145]

[0146] The groups that appear therein have the meanings given in Formula II above, and

[0147] Preferably

[0148] R 2 It represents H, an alkyl or alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0149] in and One of them means

[0150] And another independent representation

[0151]

[0152]

[0153] Preferably representing

[0154]

[0155] Most preferred option

[0156]

[0157] And preferably

[0158] R 2 C represents n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0159] n represents an integer in the range of 0 to 15, preferably an integer in the range of 1 to 7, and particularly preferably an integer in the range of 1 to 5.

[0160] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0161] The compounds of formula II-1 are preferably selected from compounds of formulas II-1a to II-1f:

[0162]

[0163]

[0164] in

[0165] R 2 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0166] n independently represents integers in the range of 0 to 15, preferably integers in the range of 1 to 7, particularly preferably integers in the range of 1 to 5, and

[0167] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0168] The compounds of formula II-2 are preferably selected from compounds of formulas II-2a and II-2b:

[0169]

[0170] in

[0171] R 2 Having the above meanings, C is preferred. n H 2n+1 Or CH2=CH-(CH2) Z ,

[0172] n represents an integer in the range of 0 to 15, preferably an integer in the range of 1 to 7, and particularly preferably an integer in the range of 1 to 5.

[0173] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0174] Compounds of formula II-3 are preferably selected from compounds of formulas II-3a to II-3d:

[0175]

[0176] in

[0177] R 2 Having the above meanings, C is preferred. n H 2n+1 Or CH2=CH-(CH2) Z ,

[0178] n represents an integer in the range of 0 to 15, preferably an integer in the range of 1 to 7, and particularly preferably an integer in the range of 1 to 5.

[0179] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0180] The compounds of formula III are preferably selected from compounds of formulas III-1 to III-6, more preferably from compounds of formulas III-1, III-2, III-3 and III-4, and particularly preferably from compounds of formula III-1.

[0181]

[0182]

[0183] in

[0184] Z 31 and Z 32 They represent the trans-CH=CH- or trans-CF=CF- independently, and alternatively in Equation III-6, Z 31 and Z 32 One of them can represent -C≡C- and the other groups have the meanings in Formula III above.

[0185] And preferably

[0186] R 3 It represents H, an alkyl or alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0187] to One of them, preferred express

[0188]

[0189] Preferably representing

[0190] And other expressions that are independent of each other

[0191]

[0192]

[0193] Preferably

[0194]

[0195] More preferably

[0196]

[0197] in Alternative representation

[0198] And preferably

[0199] R 3 C represents n H 2n+1 Or CH2=CH-(CH2) Z ,

[0200] n represents an integer in the range of 0 to 15, preferably an integer in the range of 1 to 7, and particularly preferably an integer in the range of 1 to 5.

[0201] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0202] The compounds of formula III-1 are preferably selected from compounds of formulas III-1a to III-1l, more preferably from compounds of formulas III-1a, III-1b, III-1h and III-1i, and particularly preferably from formulas III-1b and / or III-1h:

[0203]

[0204]

[0205] in

[0206] R 3 Having the above meanings, C is preferred. n H 2n+1 Or CH2=CH-(CH2) Z ,

[0207] n represents an integer in the range of 0 to 15, preferably an integer in the range of 1 to 7, and particularly preferably an integer in the range of 1 to 5.

[0208] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0209] Compounds of formula III-2 are preferably compounds of formulas III-2a to III-2l, with III-2b and / or III-2j being particularly preferred:

[0210]

[0211]

[0212] in

[0213] R 3 Having the above meanings, C is preferred. n H 2n+1 Or CH2=CH-(CH2) Z Or cycloalkyl groups having 3 to 10 carbon atoms,

[0214] n represents an integer in the range of 0 to 15, preferably an integer in the range of 1 to 7, and particularly preferably an integer in the range of 1 to 5.

[0215] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0216] Very preferably, the medium comprises one or more compounds of formula III-2j selected from the following formulas III-2j-1 to III-2j-15:

[0217]

[0218]

[0219]

[0220] Compounds of formula III-5 are preferably selected from compounds of formula III-5a:

[0221]

[0222] R 3 Having the meaning of the above formula III-5, it is preferred to represent C.n H 2n+1 Where n represents an integer in the range of 0 to 7, preferably an integer in the range of 1 to 5. The compounds of formula III-6 are preferably selected from compounds of formulas III-6a to III-6l.

[0223]

[0224]

[0225] In a preferred embodiment, the medium according to the invention comprises one or more compounds selected from formulas IIA-1-1 to IIA-1-12, with compounds of IIA-1-1 or IIA-1-2 being particularly preferred:

[0226]

[0227]

[0228] in

[0229] 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.

[0230] R L Each occurrence may refer to 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 cyclopent-1-alkenyl, with ethyl being very preferred.

[0231] And compounds of formula II-1 are excluded from it.

[0232] Furthermore, in certain embodiments of the liquid crystal medium according to the invention, which may be the same as or different from the previously preferred embodiments, it preferably comprises one or more compounds of formula IV.

[0233]

[0234] in

[0235]

[0236] express

[0237]

[0238] s is 0 or 1, preferably 1, and

[0239] Preferably

[0240]

[0241] express

[0242]

[0243] Particularly preferred means

[0244]

[0245] 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, particularly preferably CH3, C2H5, cyclopropyl, or cyclobutyl.

[0246] X 4 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.

[0247] R 41 To R 44 Each of the above can independently represent an alkyl or alkoxy group having 1 to 15 carbon atoms, an alkenyl, alkenyloxy, or alkoxyalkyl group having 2 to 15 carbon atoms, or a cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl, or alkylcycloalkenylalkyl group having up to 15 carbon atoms, and alternatively, R 43 and R 44 One or two of them can also represent H.

[0248] Preferably

[0249] R 41 and R 42 Each of the above can independently represent an alkyl or alkoxy group having 1 to 7 carbon atoms, or an alkenyl, alkenoxy, or alkoxyalkyl group having 2 to 7 carbon atoms.

[0250] Particularly preferred

[0251] R 41 This indicates an alkyl group having 1 to 7 carbon atoms, or an alkenyl, alkenoxy, or alkoxyalkyl group each having 2 to 7 carbon atoms.

[0252] Particularly preferred

[0253] R 42 Indicates alkyl or alkoxy groups, each having 1 to 7 carbon atoms, and

[0254] Preferably

[0255] R43 and R 44 H represents an alkyl group having 1 to 5 carbon atoms, a cycloalkyl or cycloalkenyl group having 3 to 7 carbon atoms, an alkylcycloalkyl or cycloalkylalkyl group each having 4 to 12 carbon atoms, or an alkylcycloalkylalkyl 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.

[0256] In a preferred embodiment of the invention, the liquid crystal medium further comprises one or more compounds selected from formulas V, VI, VII, VIII, and IX:

[0257]

[0258] in

[0259] L 51 R represents 51 or X 51 ,

[0260] L 52 R represents 52 or X 52 ,

[0261] R 51 and R 52 The terms "H" and "alkoxy" can be independently represented by alkyl or alkoxy groups having 1 to 12, preferably 2 to 7, carbon atoms, or alkenyl, alkenyloxy, or alkoxyalkyl groups having 2 to 15, preferably 2 to 7, carbon atoms, with alkyl or alkenyl groups being preferred.

[0262] X 51 and X 52 Independently representing H, F, Cl, -CN, SF5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, or fluorinated alkenyl, fluorinated alkenyloxy or fluorinated alkoxyalkyl having 2 to 7 carbon atoms, preferably fluorinated alkoxy, fluorinated alkenyloxy, F or Cl, and

[0263] to Representing each other independently

[0264]

[0265] Preferably representing

[0266]

[0267] L 61 R represents 61And in Z 61 and / or Z 62 In cases where the trans form -CH=CH- or the trans form -CF=CF- is represented, it can also alternatively represent X. 61 ,

[0268] L 62 R represents 62 And in Z 61 and / or Z 62 In cases where the trans form -CH=CH- or the trans form -CF=CF- is represented, it can also alternatively represent X. 62 ,

[0269] R 61 and R 62 The terms "H" and "alkoxy" can be independently represented by alkyl or alkoxy groups having 1 to 12, preferably 2 to 7, carbon atoms, or alkenyl, alkenyloxy, or alkoxyalkyl groups having 2 to 15, preferably 2 to 7, carbon atoms, with alkyl or alkenyl groups being preferred.

[0270] X 61 and X 62 Independently representing F or Cl, -CN, SF5, fluorinated alkyl or alkoxy groups having 1 to 7 carbon atoms, or fluorinated alkenyl, alkenyl or alkoxyalkyl groups having 2 to 7 carbon atoms.

[0271] Z 61 and Z 62 One of them represents the trans-CH=CH-, trans-CF=CF-, or -C≡C-, and the other, independently of it, represents the 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.

[0272] to Representing each other independently

[0273]

[0274] Preferably representing

[0275]

[0276] and

[0277] x represents 0 or 1.

[0278] L 71 R represents 71 or X 71 ,

[0279] L 72 R represents 72 or X 72 ,

[0280] R 71 and R 72 The terms "H" and "alkoxy" can be independently represented by alkyl or alkoxy groups having 1 to 12, preferably 2 to 7, carbon atoms, or alkenyl, alkenyloxy, or alkoxyalkyl groups having 2 to 15, preferably 2 to 7, carbon atoms, with alkyl or alkenyl groups being preferred.

[0281] X 71 and X 72 Independently representing H, F, Cl, -CN, -NCS, -SF5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, or fluorinated alkenyl, fluorinated alkenyloxy or fluorinated alkoxyalkyl having 2 to 7 carbon atoms, preferably fluorinated alkoxy, fluorinated alkenyloxy, F or Cl, and

[0282] Z 71 To Z 73 Each expression independently represents a trans-CH=CH-, trans-CF=CF-, -C≡C-, or a single bond, preferably one or more of which represent single bonds, and particularly preferably all of which represent single bonds.

[0283] to Representing each other independently

[0284]

[0285] Preferably representing

[0286]

[0287] R 81 and R 82 The terms "H" and "alkyl" or "alkoxy" having 1 to 15, preferably 2 to 7, carbon atoms, or "alkenyl," "alkenoxy," or "alkoxyalkyl" having 2 to 15, preferably 2 to 7, carbon atoms, preferably alkyl or alkenyl, are used independently of each other.

[0288] Z 81 and Z 82 One of them represents the trans-CH=CH-, trans-CF=CF-, or -C≡C-, and the other, independently of it, represents the 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.

[0289] express

[0290] and Representing each other independently

[0291]

[0292] L 91 R represents 91 or X 91 ,

[0293] L 92 R represents 92 or X 92 ,

[0294] R 91 and R 92 The terms "H" and "alkyl" or "alkoxy" having 1 to 15, preferably 2 to 7, carbon atoms, or "alkenyl," "alkenoxy," or "alkoxyalkyl" having 2 to 15, preferably 2 to 7, carbon atoms, preferably alkyl or alkenyl, are used independently of each other.

[0295] X 91 and X 92 Independently representing H, F, Cl, -CN, -NCS, -SF5, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, or fluorinated alkenyl, fluorinated alkenyloxy or fluorinated alkoxyalkyl having 2 to 7 carbon atoms, preferably fluorinated alkoxy, fluorinated alkenyloxy, F or Cl, and

[0296] Z 91 To Z 93 The expressions can be independently represented as trans-CH=CH-, trans-CF=CF-, -C≡C-, or single bonds, preferably one or more of them representing single bonds, and particularly preferably all of them representing single bonds.

[0297] express

[0298] to Representing each other independently

[0299]

[0300] In a preferred embodiment of the present invention, the liquid crystal medium comprises one or more compounds of formula V, preferably compounds selected from formulas V-1 to V-3, preferably compounds selected from formulas V-1 and / or V-2 and / or V-3, and preferably compounds selected from formulas V-1 and V-2.

[0301]

[0302] The groups appearing therein have the corresponding meanings shown in Formula V above, preferably

[0303] R 51 This indicates an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

[0304] R52 This indicates an alkyl group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkoxy group having 1 to 7 carbon atoms.

[0305] X 51 and X 52 F, Cl, -OCF3, -CF3, -CN or -SF5 can be represented independently of each other, with F, Cl, -OCF3 or -CN being preferred.

[0306] The compounds of formula V-1 are preferably selected from compounds of formulas V-1a to V-1d, and more preferably compounds of V-1c and V-1d:

[0307]

[0308] The parameters have the corresponding meanings described in equation V-1 above, and where

[0309] Y 51 and Y 52 H or F is represented independently of each other in each case, and preferably

[0310] R 51 Indicates alkyl or alkenyl, and

[0311] X 51 It represents F, Cl, or -OCF3.

[0312] The compounds of formula V-2 are preferably selected from compounds of formulas V-2a to V-2e and / or compounds selected from formulas V-2f and V-2g:

[0313]

[0314]

[0315] In each case, compounds of formula V-2a are excluded from compounds of formulas V-2b and V-2c, compounds of formula V-2b are excluded from compounds of formula V-2c, compounds of formula V-2f are excluded from compounds of formula V-2g, and

[0316] The parameters have the corresponding meanings described in Equation V-1 above, and where...

[0317] Y 51 and Y 52 H or F is represented independently of each other in each case, and preferably

[0318] Y 51 and Y 52 One is represented by H, and the other by H or F, preferably H as well.

[0319] The compounds of formula V-3 are preferably compounds of formula V-3a:

[0320]

[0321] The parameters have the corresponding meanings shown in Equation V-1 above, and preferably...

[0322] X 51 F and Cl are preferred, with F being the preferred choice.

[0323] X 52 It can be represented as F, Cl, or -OCF3, with -OCF3 being preferred.

[0324] Compounds of formula V-1a are preferably selected from compounds of formulas V-1a-1 and V-1a-2:

[0325]

[0326] in

[0327] R 51 Having the above meanings, C is preferred. n H 2n+1 ,in

[0328] n represents an integer in the range of 0 to 7, preferably an integer in the range of 1 to 5, and particularly preferably 3 or 7.

[0329] The compounds of formula V-1b are preferably compounds of formula V-1b-1:

[0330]

[0331] in

[0332] R 51 Having the above meanings, C is preferred. n H 2n+1 , where n represents an integer in the range of 0 to 15, preferably an integer in the range of 1 to 7, and particularly preferably 1 to 5.

[0333] The compounds of formula V-1c are preferably selected from compounds of formulas V-1c-1 to V-1c-4, and particularly preferably from compounds of formulas V-1c-1 and V-1c-2:

[0334]

[0335] in

[0336] R 51 Having the above meanings, C is preferred. n H 2n+1 ,in

[0337] n represents an integer in the range of 0 to 15, preferably an integer in the range of 1 to 7, and particularly preferably 1 to 5.

[0338] Compounds of formula V-1d are preferably selected from compounds of formulas V-1d-1 and V-1d-2, with compounds of formula V-1d-2 being particularly preferred.

[0339]

[0340] in

[0341] R 51 Having the above meanings, C is preferred. n H 2n+1 ,in

[0342] n represents an integer in the range of 1 to 7, preferably an integer in the range of 2 to 6, and particularly preferably 2 to 5.

[0343] Compounds of formula V-2a are preferably selected from compounds of formulas V-2a-1 and V-2a-2, with compounds of formula V-2a-1 being particularly preferred.

[0344]

[0345] in

[0346] R 51 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0347] R 52 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0348] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, particularly preferably integers in the range of 2 to 5, and

[0349] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0350] (R 51 and R 52 The preferred combination, especially in the case of formula V-2a-1, is (C n H 2n+1 and C m H 2m+1 ), (C n H 2n+1 and OCm H 2m+1 (CH2=CH-(CH2)) Z and C m H 2m+1 (CH2=CH-(CH2)) Z and OC m H 2m+1 ) and (C n H 2n+1 and (CH2) Z -CH=CH2).

[0351] The preferred compound of formula V-2b is the compound of formula V-2b-1:

[0352]

[0353] R 51 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0354] R 52 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0355] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, particularly preferably integers in the range of 2 to 5, and

[0356] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0357] Here (R) 51 and R 52 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ).

[0358] The preferred compound of formula V-2c is the compound of formula V-2c-1:

[0359]

[0360] in

[0361] R 51 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2)Z ,and

[0362] R 52 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0363] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, particularly preferably integers in the range of 2 to 5, and

[0364] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0365] Here (R) 51 and R 52 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ).

[0366] The preferred compound of formula V-2d is the compound of formula V-2d-1:

[0367]

[0368] in

[0369] R 51 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0370] R 52 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0371] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, particularly preferably integers in the range of 2 to 5, and

[0372] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0373] Here (R) 51 and R 52 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ).

[0374] The preferred compound of formula V-2e is the compound of formula V-2e-1:

[0375]

[0376] in

[0377] R 51 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0378] R 52 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0379] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, particularly preferably integers in the range of 2 to 5, and

[0380] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0381] Here (R) 51 and R 52 The preferred combination is (C) n H 2n+1 and OC m H 2m+1 ).

[0382] The preferred compound of formula V-2f is the compound of formula V-2f-1:

[0383]

[0384] in

[0385] R 51 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0386] R 52 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0387] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, particularly preferably integers in the range of 2 to 5, and

[0388] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0389] Here (R) 51 and R 52 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0390] The preferred compound of formula V-2g is the compound of formula V-2g-1:

[0391]

[0392] in

[0393] R 51 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0394] R 52 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0395] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, particularly preferably integers in the range of 2 to 5, and

[0396] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0397] Here (R) 51 and R 52 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H2m+1 ), especially preferred (C) n H 2n+1 and OC m H 2m+1 ).

[0398] The compounds of formula VI are preferably selected from compounds of formulas VI-1 to VI-5:

[0399]

[0400] in

[0401] Z 61 and Z 62 The expression -C≡C-, trans-CH=CH-, or trans-CF=CF-, preferably -C≡C- or trans-CH=CH-, and other appearing groups and parameters have the meanings described in VI above.

[0402] And preferably

[0403] R 61 and R 62 Each can be independently represented as an alkyl or alkoxy group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

[0404] X 62 This indicates F, Cl, -OCF3, or -CN.

[0405] The compounds of formula VI-1 are preferably selected from compounds of formulas VI-1a and VI-1b, and more preferably from compounds of formula VI-1a:

[0406]

[0407] in

[0408] R 61 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0409] R 62 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0410] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, particularly preferably integers in the range of 2 to 5, and

[0411] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0412] Here (R) 61 and R 62 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 In the case of formula VI-1a, it is particularly preferred (C) n H 2n+1 and C m H 2m+1 And in the case of formula VI-1b, it is particularly preferred that (C) n H 2n+1 and OC m H 2m+1 ).

[0413] The compounds of formula VI-3 are preferably selected from compounds of formulas VI-3a to VI-3e:

[0414]

[0415] The parameters have the meaning given in equation VI-3 above, and preferably R 61 Having the above meanings, C is preferred. n H 2n+1 ,in

[0416] n represents an integer in the range of 1 to 7, preferably an integer in the range of 2 to 5, and X 62 It represents -F, -Cl, -OCF3, or -CN.

[0417] The compounds of formula VI-4 are preferably selected from compounds of formulas VI-4a to VI-4e:

[0418]

[0419] The parameters have the meaning given in equation VI-4 above, and preferably R 61 Having the above meanings, C is preferred. n H 2n+1 ,in

[0420] n represents an integer in the range of 1 to 7, preferably an integer in the range of 2 to 5, and X 62 It represents -F, -Cl, -OCF3, or -CN.

[0421] The compounds of formula VI-5 are preferably selected from compounds of formula VI-5a to VI-5d, with VI-5b being the most preferred:

[0422]

[0423] The parameters have the meaning given in equation VI-5 above, and preferably R 61 Having the above meanings, C is preferred. n H 2n+1 Where n represents an integer in the range of 1 to 7, preferably an integer in the range of 2 to 5, and X 62 It can be represented as -F, -Cl, -OCF3 or -CN, with -OCF3 being particularly preferred.

[0424] The compounds of formula VII are preferably selected from compounds of formulas VII-1 to VII-6:

[0425]

[0426]

[0427] The compounds of formula VII-5 are excluded from the compounds of formula VII-6, and

[0428] The parameters have the corresponding meanings shown in equation VII above.

[0429] Y 71 Y 72 Y 73 H or F can be represented independently of each other.

[0430] And preferably

[0431] R 71 This indicates an alkyl or alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0432] R 72 This indicates an alkyl or alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0433] X 72 Indicates F, Cl; NCS or -OCF3, preferably F or NCS, and

[0434] Particularly preferred

[0435] R 71 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0436] R 72 Having the above meaning, and preferably representing C m H 2m+1 or OCm H 2m+1 Or (CH2) Z -CH = CH2, where

[0437] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0438] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0439] The compounds of formula VII-1 are preferably selected from compounds of formulas VII-1a to VII-1d:

[0440]

[0441] Where X 72 It has the meaning given in equation VII-2 above.

[0442] R 71 Having the above meanings, C is preferred. n H 2n+1 ,in

[0443] n represents 1 to 7, preferably 2 to 6, particularly preferably 2, 3 or 5, and

[0444] Z represents 0, 1, 2, 3, or 4, preferably 0 or 2, and

[0445] X 72 Preferably, F is used.

[0446] The compounds of formula VII-2 are preferably selected from those of formulas VII-2a and VII-2b, with compounds of formula VII-2a being particularly preferred.

[0447]

[0448] in

[0449] R 71 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0450] R 72 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0451] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0452] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0453] Here (R) 71 and R 72 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0454] The compounds of formula VII-3 are preferably compounds of formula VII-3a:

[0455]

[0456] in

[0457] R 71 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0458] R 72 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0459] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0460] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0461] Here (R) 71 and R 72 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OCm H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0462] The compounds of formula VII-4 are preferably compounds of formula VII-4a:

[0463]

[0464] in

[0465] R 71 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0466] R 72 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0467] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0468] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0469] Here (R) 71 and R 72 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0470] The compounds of formula VII-5 are preferably selected from compounds of formula VII-5a and VII-5b, and more preferably compounds of formula VII-5a:

[0471]

[0472]

[0473] in

[0474] R 71 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0475] R 72 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0476] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0477] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0478] Here (R) 71 and R 72 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0479] The compounds of formula VII-6 are preferably selected from compounds of formulas VII-6a and VII-6b:

[0480]

[0481] in

[0482] R 71 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0483] R 72 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z-CH = CH2, where

[0484] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0485] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0486] Here (R) 71 and R 72 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0487] The compounds of formula VII-7 are preferably selected from those of formulas VII-7a and VII-7d:

[0488]

[0489] in

[0490] R 71 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,

[0491] X 72 Indicates F, -OCF3, or -NCS.

[0492] n represents an integer in the range of 1 to 7, preferably an integer in the range of 2 to 6, and particularly preferably an integer in the range of 2 to 5.

[0493] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0494] The compounds of formula VIII are preferably selected from compounds of formulas VIII-1 to VIII-3, more preferably these compounds of formula VIII consist mainly of, even more preferably substantially of, and very particularly preferably entirely of the following substances:

[0495]

[0496] in

[0497] Y 81 and Y82 One represents H, the other represents H or F, and

[0498] R 81 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0499] R 82 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0500] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0501] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0502] Here (R) 81 and R 82 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0503] The compounds of formula VIII-1 are preferably selected from compounds of formulas VIII-1a to VIII-1c:

[0504]

[0505]

[0506] in

[0507] R 81 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0508] R 82 Having the above meaning, and preferably representing C m H2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0509] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0510] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0511] Here (R) 81 and R 82 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0512] The compounds of formula VIII-2 are preferably compounds of formula VIII-2a:

[0513]

[0514] in

[0515] R 81 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0516] R 82 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0517] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0518] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0519] Here (R) 81 and R 82The preferred combination is (C) n H 2n+1 and C m H 2m+1 ), (C n H 2n+1 and OC m H 2m+1 ) and, (CH2=CH-(CH2) Z and C m H 2m+1 ), especially preferred (C) n H 2n+1 and C m H 2m+1 ).

[0520] The compounds of formula VIII-3 are preferably compounds of formula VIII-3a:

[0521]

[0522] in

[0523] R 81 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0524] R 82 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0525] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0526] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0527] Here (R) 81 and R 82 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ).

[0528] The compounds of formula IX are preferably selected from compounds of formulas IX-1 to IX-3:

[0529]

[0530]

[0531] The parameters have the corresponding meanings shown in Equation IX above, and preferably...

[0532] to One of them means

[0533] and

[0534] in

[0535] R 91 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0536] R 92 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0537] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0538] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0539] Here (R) 91 and R 92 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ).

[0540] The compounds of formula IX-1 are preferably selected from compounds of formulas IX-1a to IX-1e:

[0541]

[0542]

[0543] The parameters have the above meanings and are preferably...

[0544] R91 Having the above meaning and preferably representing C n H 2n+1 ,and

[0545] n represents an integer in the range of 1 to 7, preferably an integer in the range of 2 to 6, and particularly preferably an integer in the range of 2 to 5.

[0546] X 92 Preferably, it represents F or Cl.

[0547] The compounds of formula IX-2 are preferably selected from the group consisting of compounds of formula IX-2a and IX-2b:

[0548]

[0549] in

[0550] R 91 Having the above meaning, and preferably representing C n H 2n+1 Or CH2=CH-(CH2) Z ,and

[0551] R 92 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0552] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0553] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0554] Here (R) 91 and R 92 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ).

[0555] The compounds of formula IX-3 are preferably compounds of formulas IX-3a and IX-3b:

[0556]

[0557] in

[0558] R 91 Having the above meaning, and preferably representing C n H 2n+1Or CH2=CH-(CH2) Z ,and

[0559] R 92 Having the above meaning, and preferably representing C m H 2m+1 or OC m H 2m+1 Or (CH2) Z -CH = CH2, where

[0560] n and m independently represent integers in the range of 1 to 7, preferably integers in the range of 2 to 6, and particularly preferably integers in the range of 2 to 5.

[0561] z represents 0, 1, 2, 3 or 4, preferably 0 or 2.

[0562] Here (R) 91 and R 92 The preferred combination is (C) n H 2n+1 and C m H 2m+1 ) and (C n H 2n+1 and OC m H 2m+1 ), especially preferred (C) n H 2n+1 and OC m H 2m+1 ).

[0563] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula X.

[0564]

[0565] in

[0566] R 101 The symbol represents H, an alkyl or alkoxy group having 1 to 15, preferably 2 to 7, carbon atoms, or an alkenyl, alkenyloxy, or alkoxyalkyl group having 2 to 15, preferably 2 to 7, carbon atoms, preferably alkyl or alkenyl.

[0567] X 101 This refers to H, F, Cl, -CN, SF5, NCS, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, or fluorinated alkenyl, fluorinated alkenyloxy or fluorinated alkoxyalkyl having 2 to 7 carbon atoms, preferably fluorinated alkoxy, fluorinated alkenyloxy, F, Cl or NCS, particularly preferably NCS.

[0568] Y 101 Indicates methyl, ethyl, or Cl.

[0569] Y102 It represents H, methyl, ethyl, F or Cl, preferably H or F.

[0570] Z 101 Z 102 The same or different representations of single bonds, -CH = CH-, CF = CF- or -C ≡ C-,

[0571] and Representing each other independently

[0572]

[0573] Preferably representing

[0574] And among them Alternative representation and

[0575] n is 0 or 1.

[0576] Preferably, the compound of formula X is selected from sub-formulas X-1 and X-2.

[0577]

[0578] The groups and parameters that appear have the meanings given in the above formula X.

[0579] Particularly preferably, the medium according to the invention comprises one or more compounds selected from formulas X-1-1 to X-1-9.

[0580]

[0581]

[0582] In a preferred embodiment, the medium according to the invention comprises one or more compounds of formula XI.

[0583]

[0584] in

[0585] R S The expression represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenoxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups may be... Substitution, and one or more of the H atoms can be substituted by F.

[0586] and Each occurrence is represented independently.

[0587]

[0588]

[0589] Where R L Each time it appears, it may represent H, Cl, or a straight-chain, branched, or cyclic alkyl group having 1 to 6 carbon atoms, either identically or differently.

[0590] L S1 L S2 They may represent H, Cl, or F in the same or different ways.

[0591] R S1 R S2 The same or different representations of H, alkyl or alkenyl groups having up to 6 carbon atoms, or cyclopropyl, cyclobutyl, cyclopentenyl or cyclopentyl.

[0592] R Th1 R Th2 The same or different representations of H, alkyl or alkenyl or alkoxy groups having up to 6 carbon atoms, or cyclopropyl, cyclobutyl, cyclopentenyl or cyclopentyl groups.

[0593] Z S1 Z S2 Z S3 The same or different representations of -CH=CH-, CH=CF-, -CF=CH-, -CF=CF-, -C≡C-, or single bonds,

[0594] a and b are either the same or different, either 0 or 1.

[0595] Preferably, the compound of formula XI is selected from compounds of formulas XI-1 to XI-24:

[0596]

[0597]

[0598]

[0599]

[0600] The groups appearing therein have the meanings given in formula XI above, and preferably...

[0601] R S It represents an alkyl or alkenyl group having 2 to 6 carbon atoms, wherein one or more CH2- groups can be... Replacement

[0602] R S1 and R S2 H or alkyl groups having 1 to 6 carbon atoms, either the same or different, are preferred.

[0603] R S3 The symbol 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.

[0604] L S1 and L S2 H or F may be represented in the same or different ways, with F being preferred.

[0605] Preferably, the medium according to the invention comprises one or more compounds of formula T.

[0606]

[0607] in

[0608] R T Indicates halogen, CN, NCS, R F R F -O- or R F -S, where

[0609] R F It indicates a fluorinated alkyl or fluorinated alkenyl group having up to 12 carbon atoms.

[0610] and

[0611] Each occurrence is represented independently.

[0612]

[0613] L 4 and L 5 The same or different F, Cl or straight-chain or branched or cyclic alkyl or alkenyl groups each having up to 12 C atoms;

[0614] Z T3 Z T4 They may represent -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C- or single bonds, and the same or different.

[0615] t is 0 or 1.

[0616] In a preferred embodiment, the liquid crystal medium according to the present invention comprises one or more compounds selected from the following formulas T-1a to T-3b:

[0617]

[0618] in

[0619] and And possessing the above meanings and

[0620] n is 1, 2, 3, 4, 5, 6 or 7, preferably 1, 2, 3 or 4, and especially preferably 1.

[0621] In a particularly preferred embodiment of the invention, the medium comprises one or more compounds selected from formulas T-1a and T-2a.

[0622] Preferred compounds of formula T-1a are selected from compounds of the following formulas:

[0623]

[0624]

[0625] Where n can be 1, 2, 3 or 4, preferably 1.

[0626] Preferred compounds of formula T-2a are selected from compounds with the following formulas:

[0627]

[0628]

[0629] Where n can be 1, 2, 3 or 4, preferably 1.

[0630] Very preferably, the medium comprises one or more compounds of formula T-1a-5.

[0631] Preferably, the medium contains a compound of formula C.

[0632]

[0633] in

[0634] R C The symbol represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenoxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups may be... Substitution, or indicating group R P ,

[0635] R P Indicates halogen, CN, NCS, R F R F -O- or R F -S, where

[0636] R F It indicates a fluorinated alkyl or fluorinated alkenyl group having up to 9 carbon atoms.

[0637] Z C1 Z C2The same or different representations can be -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, or a single bond, preferably -C≡C- or a single bond.

[0638] X represents Cl or F, preferably F.

[0639] Y represents H, Cl, F, an alkyl or alkoxy group each having 1 to 6 carbon atoms, preferably H, F, CH3 or C2H5, and very preferably H.

[0640] t is 0, 1, or 2, preferably 0 or 1, and

[0641] and Groups selected from the following groups:

[0642] 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.

[0643] b) The group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, bicyclo[1.1.1]pentan-1,3-diyl, 4,4'-bicyclohexylene, bicyclo[2.2.2]octan-1,4-diyl, and spiro[3.3]heptan-2,6-diyl, wherein one or more non-adjacent CH2 groups may be substituted with -O- and / or -S-, and wherein one or more H atoms may be substituted with F.

[0644] 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 be mono- or poly-substituted by L, wherein

[0645] L, in each instance, may refer to F, Cl, CN, SCN, SF5, or a straight or branched alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy, or alkoxy carbonyloxy group having 1 to 12 carbon atoms, either identically or differently.

[0646] Compounds of formula C are preferably selected from compounds of the following sub-formulas:

[0647]

[0648]

[0649]

[0650] in

[0651] L 1 L 2 and L3 The same or different representations of H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclopentenyl, and

[0652] R C X has the above meaning, and preferably

[0653] R C R represents an alkyl group or group having 1 to 7 carbon atoms. P ,

[0654] Where R P Preferably, it represents a perfluorinated alkoxy group having 1 to 7 carbon atoms, and

[0655] X represents F.

[0656] Preferably, the group Z of formula C C1 and Z C2 One of them represents a single bond, Z C1 and Z C2 Another representation of -C≡C- is found in [the original text].

[0657] The most preferred C-type compounds are selected from compounds with the following sub-formulas:

[0658]

[0659]

[0660]

[0661] Where R C With the above meaning, it preferably refers to an alkyl group or CF3O having 1 to 7 carbon atoms.

[0662] The most particularly preferred compounds are those of formulas C-7-1, C-9-1, C-9-4, C-10-1, C-10-2, C-10-3, C-10-4, C-10-5, C-10-6 and C-10-7.

[0663] Preferably, the medium comprises one or more compounds of formula U.

[0664] Formula U compound

[0665]

[0666] in

[0667] R U The symbol represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenoxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups may be... Substitution, or indicating group R P ,

[0668] R P Indicates halogen, CN, NCS, R F R F -O- or R F -S, where

[0669] R F It indicates a fluorinated alkyl or fluorinated alkenyl group having up to 9 carbon atoms.

[0670] Z U1 Z U2 Z U3 The same or different representations can be -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, or a single bond, preferably -C≡C- or a single bond.

[0671] X 1 X 2 The same or different representations may be H, Cl, F, CH3 or C2H5, with F being preferred.

[0672] Y 1 Y 2 Y 3 Y 4 The same or different representations of H, F, Cl, or straight-chain or branched or cyclic alkyl, alkenyl, alkoxy, or alkenyloxy groups each having up to 12 carbon atoms, wherein Y 1 Y 2 Y 3 and Y 4 At least one of them is different from F.

[0673] s can be 0, 1, or 2, preferably 0 or 1.

[0674] t is 0, 1, or 2, preferably 0 or 1, and

[0675] s+t can be 0, 1, or 2, preferably 0 or 1.

[0676] and Groups selected from the following groups:

[0677] 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.

[0678] b) The group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, bicyclo[1.1.1]pentan-1,3-diyl, 4,4'-bicyclohexylene, bicyclo[2.2.2]octan-1,4-diyl, and spiro[3.3]heptan-2,6-diyl, wherein one or more non-adjacent CH2 groups may be substituted with -O- and / or -S-, and wherein one or more H atoms may be substituted with F.

[0679] 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 be mono- or poly-substituted by L.

[0680] L, in each instance, may refer to F, Cl, CN, SCN, SF5, or a straight or branched alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy, or alkoxy carbonyloxy group having 1 to 12 carbon atoms, either identically or differently.

[0681] Compounds of formula U are preferably selected from compounds of the following sub-formulas:

[0682] In a preferred embodiment of the invention, the compound of formula U is selected from compounds of formulas U-1 to U-20, and is very preferably selected from compounds of formulas U-1 to U13:

[0683]

[0684]

[0685]

[0686]

[0687] The groups appearing therein have the meaning of the above formula U and its sub-formulas, preferably R. U Y represents an alkyl group having 1 to 7 carbon atoms. 1 Y 2 Y 3 and Y 4 The same or different may represent H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclopentenyl, more preferably Y. 1 and Y 2 Independently represent H or F, especially H, Y 3 and Y 4 Very preferably represented by H, L 1 and L 2 The same or different are very preferably represented by H, F, methyl or ethyl, especially H.

[0688] According to one embodiment of the invention, a compound of formula U is used, wherein R U The symbol represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenoxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups may be... Alternatives, preferably alkyl groups having 1 to 12 carbon atoms.

[0689] According to another embodiment of the invention, a compound of formula U is used, wherein the group R U R represents P , where R P Indicates halogen, CN, NCS, R F R F -O- or R F -S- and where R F It indicates a fluorinated alkyl or fluorinated alkenyl group having up to 9 carbon atoms, preferably CF3 or OCF3.

[0690] Preferably, the medium comprises one or more compounds of formula UF.

[0691] This invention relates to compounds of formula UF.

[0692]

[0693] in

[0694] R T The symbol represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenoxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups may be... Substitution, or indicating group R P ,

[0695] R P Indicates halogen, CN, NCS, R F R F -O- or R F -S, where

[0696] R F It indicates a fluorinated alkyl or fluorinated alkenyl group having up to 9 carbon atoms.

[0697] Z T1 Z T2 The same or different representations can be -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, or a single bond, preferably -C≡C- or a single bond.

[0698] X 1 X 2 X 3and X 4 Cl or F may be represented in the same or different ways, with F being preferred.

[0699] t is 0 or 1, and

[0700] and Groups selected from the following groups:

[0701] a) The group consisting of 1,4-phenylene, 1,4-naphthylene, and 2,6-naphthylene, wherein one or both CH groups may be substituted with N, and one or more H atoms may be substituted with L, wherein tetrafluoro-1,4-phenylene is excluded.

[0702] b) The group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, bicyclo[1.1.1]pentan-1,3-diyl, 4,4'-bicyclohexylene, bicyclo[2.2.2]octan-1,4-diyl, and spiro[3.3]heptan-2,6-diyl, wherein one or more non-adjacent CH2 groups may be substituted with -O- and / or -S-, and wherein one or more H atoms may be substituted with F.

[0703] 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 be mono- or poly-substituted by L.

[0704] L, in each instance, may refer to F, Cl, CN, SCN, SF5, or a straight or branched alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkyl carbonyloxy, or alkoxy carbonyloxy group having 1 to 12 carbon atoms, either identically or differently.

[0705] Compounds of formula UF are preferably selected from the following sub-formulas:

[0706]

[0707]

[0708]

[0709] in

[0710] L 1 L 2 and L 3 The same or different representations of H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclopentenyl, and

[0711] R T X 1 X 2 X 3 and X4 It has the above meaning.

[0712] According to one embodiment of the invention, a compound of formula UF is used, wherein R U The symbol represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, or an alkenyl, alkenoxy, or alkoxyalkyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups may be... Alternatives, preferably alkyl groups having 1 to 12 carbon atoms.

[0713] According to another embodiment of the invention, a compound of formula UF is used, wherein the group R U R represents P , where R P Indicates halogen, CN, NCS, R F R F -O- or R F -S- and where R F It indicates a fluorinated alkyl or fluorinated alkenyl group having up to 9 carbon atoms, preferably CF3 or OCF3.

[0714] 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 10μm -1 Up to 100μm -1 Within the range. When the medium contains two or more chiral dopants, the HTP values ​​of these dopants may have opposite signs. For some specific embodiments, this condition is preferred because it allows for some compensation of the chirality of the respective compounds and can therefore be used to compensate for various temperature-dependent properties of the resulting medium in the device. However, generally, most, preferably all, chiral compounds present in the medium according to the invention preferably have HTP values ​​with the same sign.

[0715] Preferably, the chiral dopant present in the medium according to this application is a mesocrystalline compound, and most preferably it exhibits a liquid crystal phase.

[0716] In a preferred embodiment of the invention, the medium comprises two or more chiral compounds, all having the same HTP algebraic symbol.

[0717] The temperature dependence of HTP of a single compound can be high or low. The temperature dependence of the pitch of the medium can be compensated by mixing compounds with different HTP temperature dependencies in appropriate ratios.

[0718] For optically active components, a wide range 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).

[0719] 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 the chiral groups.

[0720] Suitable chiral groups are, for example, chiral branched hydrocarbon groups, chiral ethylene glycols, naphthols, or dioxanes, and are also selected from 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, of monovalent or polyvalent chiral groups.

[0721] Preferred chiral groups are sugar derivatives, such as glucose, mannose, galactose, fructose, arabinose, and dextrose; sugar alcohols, such as sorbitol, mannitol, idole, galactitol, or their dehydrated derivatives, particularly disohydrated hexotols, such as disohydrated sorbitan (1,4:3,6-disohydrated-D-sorbitan, isosorbitan), disohydrated mannitol (isosorbitol), or disohydrated idole (isoidole); and sugar acids, such as gluconic acid and gulonic acid. (acid) and gulolose; chiral substituted diol groups, such as mono- or oligoethylene glycol or propylene glycol, wherein one or more CH2 groups are substituted by alkyl or alkoxy groups; amino acids, such as alanine, valine, phenylglycine or phenylalanine or sequences of 1 to 5 of these amino acids; steroid derivatives, such as cholesterol or cholic acid groups; terpene derivatives, such as menthyl, neomenthyl, camphenyl, pinenyl, terpinenyl, isolongifolyl, flavyl, carreyl, myrtyl, nopyl, geraniyl, linaloyl, neryl, citronellol or dihydrocitronellol.

[0722] The medium according to the invention preferably comprises a chiral dopant selected from known chiral dopants. Suitable chiral groups and mesocrystalline chiral compounds are described, for example, in DE 34 25 503, DE 3534 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 are also compounds listed in Table F below.

[0723] The chiral compounds preferred for use according to the present invention are selected from the following formulas.

[0724] Chiral dopants selected from compounds of the following formulas Al to A-III and A-Ch are particularly preferred.

[0725]

[0726]

[0727] in

[0728] R a11 R a12 and R b12 Each of the above can independently represent an alkyl group having 1 to 15 carbon atoms, and one or more of the non-adjacent CH2 groups can each be independently converted to -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 one or more of the H atoms may be substituted by F, Cl, Br, I or CN, preferably representing an alkyl group, more preferably a n-alkyl group, provided that R a12 With R b12 different,

[0729] R a21 and R a22 Each of the above can independently represent an alkyl group having 1 to 15 carbon atoms, and one or more of the non-adjacent CH2 groups can each be independently converted to -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 one or more of the H atoms can be replaced by F, Cl, Br, I, or CN, preferably both representing alkyl, more preferably n-alkyl.

[0730] R a31 R a32 and R b32 Each of these groups independently represents a straight-chain or branched alkyl group having 1 to 15 carbon atoms, and one or more of these non-adjacent CH2 groups may 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 one or more of the H atoms can be replaced by F, Cl, Br, I, or CN, preferably representing an alkyl group, more preferably a n-alkyl group, provided that R a32 With different R b32 ;

[0731] R z It can represent H, CH3, F, Cl or CN, preferably H or F.

[0732] R 8 With the R given above a11 One meaning of "" is preferably alkyl, more preferably n-alkyl having 1 to 15 carbon atoms.

[0733] Z 8 Represents -C(O)O-, CH2O, CF2O, or a single bond, preferably -C(O)O-, A 11 The following is text A 12 Defined, or alternatively represented

[0734]

[0735] A 12 express

[0736] Preferably representing

[0737] in

[0738] L 12 Each occurrence independently represents a halogen, CN, or an alkyl, alkenyl, alkoxy, or alkenyloxy group having up to 12 C atoms, with one or more H atoms optionally replaced by a halogen; preferably methyl, ethyl, Cl, or F; particularly preferably F, A. 21 express

[0739]

[0740] A 22 With targeting A 12 The meaning given,

[0741] A 31 With targeting A 11 The given meaning, or alternative representation

[0742] A 32 With targeting A 12 The meaning given,

[0743] n2 is 0, 1, or 2 each time it appears, and

[0744] n3 is 1, 2, or 3, and

[0745] r can be 0, 1, 2, 3, or 4.

[0746] Particularly preferred are dopants selected from compounds of the following formula:

[0747]

[0748]

[0749] in

[0750] m is an integer from 1 to 9, either identically or differently, in each occurrence.

[0751] n is an integer from 2 to 9, either the same or different, each time it appears.

[0752] The particularly preferred compound of formula A is compound of formula A-III.

[0753] Other preferred dopants are derivatives of isosorbide, isomannitol, or iso-idole of formulas A-IV:

[0754]

[0755] Among them, groups yes

[0756] (desaturated sorbitol)

[0757] (disohydrated mannitol) or

[0758] (Disohydrated Idole),

[0759] The preferred option is dehydrosorbitol.

[0760] And chiral ethylene glycols, such as diphenylethylene glycol (hydrogenated benzoin), especially mesocrystalline hydrogenated benzoin derivatives of the following formula AV:

[0761]

[0762] Including (S,S) mirror isomers not shown,

[0763] in and Each is independently 1,4-phenylene, which can also be mono-, di-, or tri-substituted with L; or 1,4-cyclohexylene.

[0764] L is H, F, Cl, CN, or an optional halogenated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkoxycarbonyloxy group having 1 to 7 carbon atoms.

[0765] c is 0 or 1

[0766] X is CH2 or -C(O)-.

[0767] Z 0 It is -COO-, -OCO-, -CH2CH2- or a single bond, and

[0768] R 0 It is an alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl or alkyl carbonyloxy group having 1 to 12 carbon atoms.

[0769] Examples of compounds of formula IV are:

[0770]

[0771]

[0772] Compounds of formula A-IV are described in WO 98 / 00428. Compounds of formula AV are described in GB-A-2,328,207.

[0773] Highly 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).

[0774] Chiral compounds of formula A-VI are particularly preferred:

[0775]

[0776] in

[0777] X 1 X 2 Y 1 and Y 2 Each 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 mono- or poly-substituted by F, Cl, Br, I or CN, and one or more of the other non-adjacent CH2 groups may be independently substituted with -O-, -S-, -NH-, NR. x-, -CO-, -COO-, -OCO-, -OCOO-, -S-CO-, -CO-S-, -CH=CH-, or -C≡C- are substituted with O and / or S atoms not directly connected to each other; polymerizable groups or cycloalkyl or aryl groups having up to 20 carbon atoms, which may optionally be mono- or poly-substituted with halogens, preferably F, or with polymerizable groups.

[0778] x 1 and x 2 Each is independently 0, 1, or 2.

[0779] y 1 and y 2 Each is independently 0, 1, 2, 3, or 4.

[0780] B 1 and B 2 Each is an aromatic or partially or fully saturated aliphatic 6-membered ring, wherein one or more CH groups may be substituted by N atoms and one or more non-adjacent CH2 groups may be substituted by O or S atoms.

[0781] W 1 and W 2 Each is independent of the others -Z 1 -A 1 -(Z 2 -A 2 ) m -R, and one of them is R instead. 1 Or A 3 However, the two cannot both be H, or

[0782] yes

[0783] U 1 and U 2 Each of these elements is independently CH2, O, S, CO, or CS.

[0784] V 1 and V 2 Each is (CH2) independently of the others. n One to four non-adjacent CH2 groups can each be replaced by O or S, and V 1 and V 2 One of them is a single bond and in yes In the case that both are single bonds,

[0785] n is 1, 2, or 3.

[0786] Z 1 and Z 2Each of the following is independent of the others: -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR x -、-NR x Combinations of two of the following groups: -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 the two O and / or S and / or N atoms are not directly connected to each other, preferably -CH=CH-COO- or -COO-CH=CH- or a single bond.

[0787] R x Indicates an alkyl group having 1 to 6 carbon atoms.

[0788] A 1 A 2 and A 3 Each of these groups is independently 1,4-phenylene, wherein one or both non-adjacent CH groups may be substituted with N; 1,4-cyclohexylene, wherein one or both non-adjacent CH2 groups may be substituted with O or S; 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 mono- or poly-substituted with L, and additionally A 1 It can be a single key.

[0789] 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.

[0790] m is independently 0, 1, 2, or 3 in each case, and

[0791] R and R 1 Each of the following is independently a 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 mono- or poly-substituted by F, Cl, Br, I, or CN, and one or more of the non-adjacent CH2 groups may be respectively substituted with -O-, -S-, -NH-, or -NR. 0-, -CO-, -COO-, -OCO-, -O-COO-, -S-CO-, -CO-S-, -CH=CH- or -C≡C- substitution, wherein the two O and / or S atoms are not directly connected to each other, or are polymerizable groups.

[0792] Particularly preferred are chiral binaphthyl derivatives of formula A-VI-1:

[0793]

[0794] Among them, rings B and R 0 and Z 0 It is as defined for equations A-IV and AV, and b is 0, 1, or 2.

[0795] In particular, those selected from formulas A-VI-1a to A-VI-1c:

[0796]

[0797]

[0798] Among them, rings B and R 0 and Z 0 It is as defined for formula A-VI-1, and

[0799] R 0 It is an alkyl group as defined with respect to formulas A-IV, or H, or having 1 to 4 carbon atoms, and

[0800] b is 0, 1, or 2.

[0801] And Z 0 In particular, -OC(O)- or single bonds.

[0802] The concentration of one or more chiral dopants in the LC medium is preferably in the range of 0.001% to 20%, more preferably 0.05% to 5%, more preferably 0.1% to 2%, and most preferably 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 with absolute HTP values ​​higher or lower than S-4011, these preferred concentrations must be proportionally reduced or increased accordingly based on the ratio of their HTP value to S-4011.

[0803] The pitch p of the LC medium or main mixture of the present invention is preferably in the range of 5 to 50 μm, more preferably 8 to 30 μm, and particularly preferably 10 to 20 μm.

[0804] Preferably, the medium according to the invention comprises a stabilizer selected from the group of antioxidants, preferably a hindered phenolic antioxidant and a hindered amine light stabilizer (HALS), more preferably a compound selected from formula ST-1 to ST-18.

[0805]

[0806]

[0807]

[0808]

[0809] in

[0810] R ST Represents H, an alkyl or alkoxy group having 1 to 15 carbon atoms, wherein one or more CH2 groups of these groups may be independently converted to -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, and -O-CO- are substitutions where the O atoms are not directly connected to each other, and one or more of the H atoms can be replaced by halogens.

[0811] express

[0812]

[0813]

[0814] Z ST Each of these can be independently represented as -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.

[0815] L 1 and L 2 Each can be independently represented as F, Cl, CF3, or CHF2, and p represents 1 or 2.

[0816] q represents 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0817] The particularly preferred ST compounds are those with the following formula:

[0818]

[0819] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n = 1 or 7.

[0820]

[0821] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n = 3

[0822]

[0823] Where n = 1, 2, 3, 4, 5, 6 or 7, preferably n = 3

[0824]

[0825]

[0826] In compounds of formula ST-3a and ST-3b, n preferably represents 3. In compounds of formula ST-2a, n preferably represents 7.

[0827] The mixture according to the invention comprises one or more stabilizers selected from compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1, and ST-12:

[0828]

[0829]

[0830] The compounds of formulas ST-1 to ST-18 are preferably present in the liquid crystal mixture according to the invention in an amount of 0.005-0.5% based on the mixture.

[0831] If the mixture according to the invention contains two or more compounds from formulas ST-1 to ST-18, then in the case of two compounds, the concentration is correspondingly increased to 0.01-1% based on the mixture.

[0832] 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%.

[0833] According to another aspect of the invention, the optical component comprises a polymer network liquid crystal, which is obtained by polymerizing one or more compounds of formula P as defined above in a liquid crystal host mixture, the liquid crystal host mixture comprising one or more compounds selected from formulas I, II and III as defined above. P is described, for example, in Peng, Fenglin, Chen, Haiwei, Tripathi, Suvagata, Twieg, Robert, Wu, Shin-Tson. (2015). Fast-response infrared phase modulator based on polymer network liquid crystal. Optical Materials Express. Vol. 5, Issue 2, pp. 265-273. doi:10.1364 / OME.5.000265.

[0834] P a -(Sp a ) s1 -A 2 -(Z a -A 1 ) n2 -(Sp b ) s2 -P b P

[0835] Each of the groups has the following meaning:

[0836] P a P b Each of them independently represents a polymerizable group.

[0837] Sp a Sp b The spacer group may be represented the same or different each time it appears.

[0838] s1 and s2 each represent 0 or 1 independently.

[0839] A 1 A 2 Each group independently represents a group selected from the following groups:

[0840] a) The group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, and 4,4'-bicyclohexylene, 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.

[0841] b) The group consisting of 1,4-phenylene and 1,3-phenylene, wherein one or both CH groups may be substituted with N, and one or more H atoms may be substituted with L.

[0842] c) The group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl, and selenophenol-2,5-diyl, each of which may be mono- or poly-substituted by L.

[0843] d) Composed of polycyclic groups consisting of saturated, partially unsaturated, or fully unsaturated groups, optionally substituted, having 5 to 20 ring carbon atoms, one or more of which may be substituted by heteroatoms, preferably selected from the group consisting of polycyclic groups.

[0844]

[0845] In these groups, one or more H atoms can be replaced by L, and / or one or more double bonds can be replaced by single bonds, and / or one or more CH groups can be replaced by N, where n2 represents 0, 1, 2, or 3.

[0846] Z a In each case, it can be represented independently as -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2). n -, where n is 2, 3, or 4, -O-, -CO-, -C(R) y R z -, -CH2CF2-, -CF2CF2- or a single bond,

[0847] L, appearing repeatedly or differently, represents F, Cl, CN, SCN, SF5, or a straight or branched chain having 1 to 12 C atoms, and in each case, optionally a fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy.

[0848] R y R z Each of these can independently represent H, F, or a straight-chain or branched alkyl group having 1 to 12 carbon atoms, wherein one or more additional H atoms may be replaced by F.

[0849] M represents -O-, -S-, -CH2-, -CHY 1 -or-CY 1 Y 2 -,and

[0850] Y 1 and Y 2Each possesses the aforementioned R independently of the others. y One of its meanings is either Cl or CN.

[0851] polymerizable group P a,b These are groups suitable for polymerization reactions (e.g., free radical or ionic chain polymerization, addition polymerization, or condensation polymerization), or groups suitable for polymer-analogous reactions (e.g., addition or condensation on the polymer backbone). Groups suitable for chain polymerization are particularly preferred, especially those containing -C=C- double bonds or -C≡C- triple bonds, and groups suitable for ring-opening polymerization, such as oxobutyl or epoxy groups.

[0852] Preferred group P a,b Choose from the following groups: CH2=CW 1 -CO-O-、CH2=CW 1 -CO-、 CH2=CW 2 -(O) k3 -、CW 1 =CH-CO-(O) k3 -、CW 1 =CH-CO-NH-, CH2=CW 1 -CO-NH-, CH3-CH=CH-O-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, HO-CW 2 W 3 -、HS-CW 2 W 3 -、HW 2 N-, HO-CW 2 W 3 -NH-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 - CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH-, HOOC-, OCN- and W 4 W 5 W 6 Si-, where W 1 It represents H, F, Cl, CN, CF3, phenyl, or alkyl groups having 1 to 5 carbon atoms, especially H, F, Cl, or CH3, W 2 and W3 Each independently represents H or an alkyl group having 1 to 5 carbon atoms, particularly H, methyl, ethyl, or n-propyl, W 4 W 5 and W 6 Each independently represents Cl, an oxaalkyl or oxacarbonylalkyl group having 1 to 5 carbon atoms, and W. 7 and W 8 Each of the above independently represents H, Cl or an alkyl group having 1 to 5 C atoms, Phe represents 1,4-phenylene, which is optionally substituted by one or more groups L different from P-Sp- as defined above, k1, k2 and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0853] The particularly preferred group P a,b Choose freely CH2=CW 1 The group consisting of -CO-O-, especially CH2=CH-CO-O-, CH2=C(CH3)-CO-O-, and CH2=CF-CO-O-, and also CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-, and (CH2=CH)2CH-O-. and

[0854] The highly preferred group P a,b It is selected from the group consisting of: acrylate, methacrylate, fluoroacrylate, and also ethyleneoxy, chloroacrylate, oxetyl, and epoxy, with acrylate or methacrylate being preferred.

[0855] Preferred spacer group Sp a,b Selected from formula Sp"-X", such that the group P a / b -Sp a / b -Conformation P a / b -Sp"-X"-, where

[0856] "Sp" represents an alkylene group having 1 to 20, preferably 1 to 12, carbon atoms, optionally mono- or polysubstituted with F, Cl, Br, I, or CN, and wherein one or more non-adjacent CH2 groups are each independently substituted with -O-, -S-, -NH-, or -N(R) 0 )-、-Si(R 00 R 000 )-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 -CO-O-、-O-CO-N(R) 00 )-、-N(R 00)-CO-N(R 00 -, -CH=CH-, or -C≡C- are substituted in a manner in which O and / or S atoms are not directly connected to each other.

[0857] X" means -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 00 )-、-N(R 00 )-CO-、-N(R 00 )-CO-N(R 00 )-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH=N-, -N=CH-, -N=N-, -CH=CR 0 -、-CY 3 =CY 4 -, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH- or single bonds

[0858] R 0 R 00 and R 000 Each independently represents H or an alkyl group having 1 to 12 carbon atoms, and

[0859] Y 3 and Y 4 Each may be represented by H, F, Cl, or CN, either the same or different.

[0860] X" is preferably -O-, -S-, -CO-, -C(O)O-, -OC(O-, -OC(O)O-, -CO-NR 0 -、

[0861] -NR 0 -CO-、-NR 0 -CO-NR 0 - or a single key.

[0862] A typical spacer group Sp" is, for example, -(CH2). p1 -、-(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR) 00 R 000 -O) p1 - where p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 00 and R 000 It has the above meaning.

[0863] The particularly preferred group Sp"-X"- is -(CH2). p1 -、-(CH2) p1 -O-、-(CH2) p1 -O-CO-、-(CH2) p1 -O-CO-O-, where p1 and q1 have the above meanings.

[0864] Particularly preferred groups Sp" are, in each case, straight-chain ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methylimino-ethylene, 1-methylalkylene, vinylene, propenylene, and butenylene.

[0865] The preferred monomers of formula P are as follows:

[0866]

[0867]

[0868]

[0869]

[0870]

[0871] Each group has the following meaning:

[0872] P 1 P 2 and P 2 Each group independently represents a polymerizable group as defined for formula P, preferably acrylate, methacrylate, fluoroacrylate, oxetyl, ethoxy, or epoxy groups.

[0873] Sp 1 Sp 2 and Sp 3 Each represents a single bond or spacer group independently of the others, preferably having the context for Sp a One of the meanings indicated, and particularly preferred to represent -(CH2). p1 -、-(CH2) p1 -O-、-(CH2) p1 -CO-O- or -(CH2) p1 -O-CO-O-, where p1 is an integer from 1 to 12, and the connection with the adjacent ring in the last mentioned group occurs through the O atom.

[0874] In addition, the group P 1 -Sp 1 -, P 2 -Sp 2 -and P 3 -Sp 3 One or more of - can represent the group R aa The condition is that P exists. 1 -Sp 1 -, P 2 -Sp 2 -and P 3 -Sp 3 - at least one of them does not represent R aa ,

[0875] R aa Represents H, F, Cl, CN, or a straight-chain or branched alkyl group having 1 to 25 C atoms, wherein one or more non-adjacent CH2 groups may be independently bounded by C(R) 0 )=C(R 00 )-、-C≡C-、-N(R 0 -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-, -O-CO-O- can be substituted in such a way that the O and / or S atoms are not directly bonded to each other, and one or more of the H atoms can be replaced by F, Cl, CN or P. 1 -Sp 1 - Alternatively preferred are straight-chain or branched groups having 1 to 12 carbon atoms, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy groups (wherein the alkenyl and alkynyl groups have at least two carbon atoms and the branched groups have at least three carbon atoms).

[0876] R 0 R 00 Each of these can be independently represented by H or an alkyl group having 1 to 12 carbon atoms.

[0877] R y and R z Each can be independently represented as H, F, CH3, or CF3.

[0878] Z p1 Represents -O-, -CO-, -C(R) y R z - or -CF2CF2-,

[0879] Z p2 and Z p3Each can be independently represented as -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2). n3 - where n3 is 2, 3, or 4.

[0880] L, appearing repeatedly or differently, represents F, Cl, CN, SCN, SF5, or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy group having 1 to 12 carbon atoms, preferably F.

[0881] L' and L” each independently represent H, F, or Cl.

[0882] r represents 0, 1, 2, 3, or 4.

[0883] s represents 0, 1, 2, or 3.

[0884] t represents 0, 1, or 2.

[0885] x represents 0 or 1.

[0886] In a particularly preferred embodiment of the invention, the LC mixture comprises one or more compounds of formula P10-1.

[0887]

[0888] The parameters are defined as described above, and P 1 and P 2 Preferably, it represents an acrylate group or a methacrylate group.

[0889] The particularly preferred compounds of formula P10-1 are selected from the following sub-formulas.

[0890]

[0891] Each n4 represents an integer between 2 and 10 independently, preferably 3, 4, 5 or 6.

[0892] In one embodiment of the invention, the liquid crystal composition is injected between the first substrate and the second substrate, or filled into the cell by capillary force after the first and second substrates are combined. In an alternative embodiment, the liquid crystal composition can be inserted between the first and second substrates by combining the second substrate with the first substrate after the liquid crystal composition has been loaded onto the first substrate.

[0893] The total amount of compound P in the medium is in the range of >0% to 20%, preferably 2% to 15%, very preferably 3% to 10%, and particularly 4%, 5%, 6%, 7% or 8%.

[0894] The polymerizable compound is polymerized or crosslinked in situ in an LC medium between the substrates of the optical component (if the polymerizable compound contains two or more polymerizable groups), optionally under the application of a voltage. Polymerization can be carried out in one step or more steps (“final curing”).

[0895] Suitable and preferred polymerization methods are, for example, thermal or photopolymerization, preferably photopolymerization, especially UV photopolymerization. One or more polymerization initiators may optionally be added. Suitable conditions for polymerization and suitable types and amounts of initiators are known to those skilled in the art and described in the literature. Commercially available photoinitiators are suitable for free radical polymerization. or (BASF SE). If an initiator is used, its proportion is preferably 0.001 to 5% by weight, particularly preferably 0.001 to 1% by weight.

[0896] The polymerizable compounds according to the invention are also suitable for initiator-free polymerization, which relates to considerable advantages, such as lower material costs and, in particular, reduced LC media contamination caused by possible residual initiators or their degradation products. Polymerization can therefore be carried out without the addition of an initiator. Thus, in a preferred embodiment, the LC media does not contain a polymerization initiator.

[0897] The polymerizable component or LC medium may also contain one or more stabilizers to prevent undesirable spontaneous polymerization of RM, such as during storage or transportation. Suitable types and amounts of stabilizers are known to those skilled in the art and are described in the literature. Particularly suitable stabilizers include, for example, commercially available... stabilizers for series (BASF SE), such as 1076. If a stabilizer is used, the proportion of the stabilizer is preferably 10-10,000 ppm, particularly preferably 50-500 ppm, based on the total amount of the RM or polymerizable components.

[0898] Other mesocrystalline compounds not explicitly mentioned above may also be optionally and advantageously used in the media according to the invention. Such compounds are known to those skilled in the art.

[0899] In a preferred embodiment of the invention, the liquid crystal medium comprises a total of 30% or more, preferably 40% or more, particularly preferably 50% or more of a compound of formula I, preferably selected from compounds of formulas I-1, I-2 and I-3, particularly preferably selected from compounds of formulas I-2 and I-3.

[0900] In another preferred embodiment of the invention, the liquid crystal medium contains a total of 20% or less, preferably 18% or less, particularly preferably 15% or less of a compound of formula I, preferably selected from compounds of formulas I-1, I-2 and I-3, particularly preferably selected from compounds of formulas I-2 and I-3.

[0901] Preferably, the proportion of the compound of formula I-1 in the medium is 20% or less, more preferably 15% or less, particularly preferably 10% or less, and very particularly preferably 5% or less.

[0902] In a preferred embodiment, the medium comprises one or more compounds of formula I-2, with a total concentration of 5% to 25%, more preferably 7% to 25%, and particularly preferably 10% to 20%.

[0903] In another preferred embodiment, the medium comprises one or more compounds of formula I-2, with a total concentration of 10% or less, preferably 5% or less, and particularly preferably 2% or less.

[0904] In a preferred embodiment, the medium contains a compound of formula I-3, preferably in the range of 5% to 50%, more preferably in the range of 10% to 40%, and particularly preferably in the range of 15% to 35%.

[0905] In a preferred embodiment, the total concentration of compound I-3 in the medium according to the invention is 20% or higher, more preferably 25% or higher, and particularly preferably 30% or higher.

[0906] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula II and / or RO-2, preferably II-1 and / or RO-2, with a total concentration of 5% to 40%, more preferably 10% to 37%, and particularly preferably 15% to 35%.

[0907] Preferably, the medium comprises one or more compounds of formula II-1.

[0908] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula II-1, with a total concentration of 25% or less, more preferably 20% or less, particularly preferably 15% or less, and very particularly preferably 10% or less.

[0909] In a preferred embodiment of the invention, the medium comprises one or more compounds of formula III, preferably III-1, and very preferably III-1b, at a total concentration of 2% to 30%, more preferably 5% to 25%, very preferably 10% to 25%, and particularly 10% to 20%.

[0910] In a preferred embodiment of the invention, the medium comprises one or more RO compounds with a total concentration of 2% to 35%, more preferably 5% to 30%, and particularly preferably 7% to 25%.

[0911] In a preferred embodiment of the invention, the liquid crystal medium preferably contains a total of 5% to 35%, more preferably 10% to 32%, and particularly preferably 20% to 30% of a compound of formula T.

[0912] In a preferred embodiment of the invention, the liquid crystal medium contains a total of 30% or less, preferably 15% or less, and particularly preferably 10% or less of a compound of formula T.

[0913] Preferably, the medium contains one or more compounds of formula C, preferably in a total concentration of 5% to 50%, more preferably 10% to 40%, and particularly preferably in the range of 15% to 30%.

[0914] Further preferred embodiments of the invention, either individually or in combination thereof, are as follows, wherein some of the compounds are abbreviated using the acronyms given in Table C:

[0915] -The medium contains one or more RO compounds and one or more T compounds;

[0916] -The medium contains one or more compounds of formula T-1;

[0917] - The medium contains one or more compounds of formula T-2;

[0918] - The medium contains one or more compounds of formulas T-1 and T-2; -

[0919] - The medium contains one or more compounds of formula T-1 and / or T-2 and one or more compounds of formula I and / or II and / or III;

[0920] -The medium contains one or more compounds of formula III-1;

[0921] -The medium contains two or more T-1 compounds;

[0922] -The medium contains two or more T-2 compounds;

[0923] -The medium includes the compound PPU-TO-S;

[0924] - The medium contains one or more RO compounds and one or more III-1 compounds, especially RO-2 and III-1b compounds, preferably in the range of 20 to 70%, more preferably in the range of 30 to 65%, very preferably in the range of 35 to 62%, and particularly preferably in the range of 40 to 60%.

[0925] - The medium contains one or more compounds of the formula PPTU-nS and / or PPTU-(cn)mS, with a total concentration in the range of 10 to 20%;

[0926] - The medium contains one or more compounds of the formula PTPU-nS and / or PTPU-(cn)mS, with a total concentration in the range of 10 to 20%;

[0927] - The medium contains one or more compounds of the formula PPTU-nS and PGTU-nS, with a total concentration in the range of 15% to 25%;

[0928] 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.

[0929] The liquid crystal medium according to the present 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.

[0930] 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, 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.

[0931] According to the liquid crystal medium of the present invention, at 1 kHz and 20 °C, Δε is preferably 10 or higher, more preferably 15 or higher, and very preferably 18 or higher.

[0932] According to the present invention, the liquid crystal medium at 589 nm (Na D The birefringence (Δn) at 20°C 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.

[0933] According to the present invention, the liquid crystal medium at 589 nm (Na D The Δn at 20°C is preferably in the range of 0.200 to 0.900, more preferably in the range of 0.250 to 0.800, even more preferably in the range of 0.300 to 0.700, and very particularly preferably in the range of 0.350 to 0.600.

[0934] 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.

[0935] In each case, the compounds of formulas I to III include dielectric positive compounds with a dielectric anisotropy greater than 3, dielectric neutral compounds with a dielectric anisotropy less than 3 and greater than -1.5, and dielectric negative compounds with a dielectric anisotropy of -1.5 or less.

[0936] The compounds of formulas I, II and III are preferably dielectric positive.

[0937] However, in some implementations, liquid crystals with negative dielectric anisotropy can also be advantageously used.

[0938] Preferably, the optical components according to the invention are arranged and configured as optical phase modulators.

[0939] In a preferred embodiment, the optical component according to the invention is designed and configured in a transparent device for phase modulation of IR radiation.

[0940] In another preferred embodiment, the optical component according to the invention is designed and configured as a reflective device for phase modulation of IR radiation.

[0941] A typical electro-optic modulator includes an infrared transmission window composed of conductive materials such as Ge, which are separated from each other by spacers and have a cell gap ranging from 1 mm to 5 mm.

[0942] According to another aspect of the invention, a LIDAR scanning system as described in WO2018 / 156643A1 is provided, comprising a laser configured to emit light pulses at an infrared operating wavelength. The LIDAR scanning system includes an emitting reconfigurable metasurface configured to reflect incident light pulses from the laser into an illumination beam directed toward a selected portion of a field of view (preferably a two-dimensional field of view). The direction of the illumination beam is responsive to a first selected holographic beam manipulation mode realized in the emitting reconfigurable metasurface. The system also includes a receiving reconfigurable metasurface configured to reflect a returned illumination beam from the selected portion of the field of view into a relay beam directed toward an optical detector. The direction of the relay beam is responsive to a second selected holographic beam manipulation mode realized in the receiving reconfigurable metasurface. The system includes the optical detector comprising an array of detector pixels. Each detector pixel includes (i) a photodetector configured to detect light in the returned illumination beam; and (ii) a timing circuit configured to determine the time of flight of the detected light. The optical detector is also configured to output a detection signal representing the detected light and the time-of-flight of the detected light for each pixel of the array. The reconfigurable metasurface includes a plurality of dynamically tunable high-Q dielectric resonators arranged on the surface of the reconfigurable metasurface, wherein the inter-component spacing is smaller than the operating wavelength of the laser, wherein the surface of the reconfigurable metasurface includes a conductive surface, and the plurality of resonators have corresponding plurality of tunable reflective phases to provide a dynamically tunable reflected wave in response to an incident wave, wherein the conductive surface and the plurality of resonators define the metasurface. Each of the plurality of dielectric resonators includes (i) paired regions having a high refractive index; and (ii) an electrically tunable material disposed in the gap between these regions, wherein the electrically tunable material is a liquid crystal material as described in the context.

[0943] According to another aspect of the invention and with reference to Figure 1 A reflective spatial light modulator, specifically an LCoS device 100, is provided, comprising a liquid crystal material 140 as defined above sandwiched between a transparent glass layer 110 having transparent electrodes 120, a mirror 150 mounted on a silicon CMOS substrate 160, and a PCB mount (not shown). The mirror is divided into a two-dimensional array of individually addressable pixels. Each pixel can be individually driven by a voltage signal to provide a local phase change to at least one polarization component of the optical signal, thereby providing a two-dimensional array of phase-manipulating regions. Pre-alignment of the liquid crystal 140 is provided by alignment layers 131 and 132.

[0944] The LCoS device is used for integration into optical devices. Preferred devices include wavelength selective switches (WSS), LIDAR scanners, infrared scene projectors, and other beam control applications shown in the article Micallef, F. (2019). Middle infrared beam-steering using liquid crystals for spatial light modulation (doctoral dissertation). https: / / doi.org / 10.17863 / CAM.39602 (https: / / www.repository.cam.ac.uk / handle / 1810 / 292443).

[0945] In this application, dielectric positivity refers to compounds or components where Δε > 3.0, dielectric neutrality refers to compounds or components where -1.5 ≤ Δε ≤ 3.0, and dielectric negativity refers to compounds or components where Δε < -1.5. Δε was measured at a frequency of 1 kHz and 20 °C. The dielectric anisotropy of the corresponding compounds was determined from the results of a 10% solution of the corresponding single compound in a nematic host mixture. If the solubility of the corresponding compound in the host mixture was less than 10%, the concentration was reduced to 5%. The capacitance of the test mixture was measured in both cells with vertical alignment and cells with planar alignment. The cell thickness of both types of cells was approximately 20 μm. The applied voltage was a rectangular wave with a frequency of 1 kHz and an effective value typically between 0.5 V and 1.0 V, but it was always chosen to be below the capacitance threshold of the corresponding test mixture.

[0946] Δε is defined as (ε || -ε ⊥ ), and ε ave. For (ε) || +2ε ⊥ ) / 3.

[0947] The host 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 determined from the changes in the corresponding values ​​of the host mixture after the addition of the compound. The concentration in the host was 10%, or 5% in cases of insufficient solubility. The values ​​were extrapolated to 100% concentration of the added compound.

[0948] In the embodiments, the phase sequence of the pure compounds is given by the following abbreviations:

[0949] K: Crystalline phase, N: Nematic phase, SmA: Smectic phase A, SmB: Smectic phase B, I:

[0950] Isotropic.

[0951] The measurements were performed on the nematic phase at a measurement temperature of 20°C, while all other components were treated as compounds.

[0952] In this application, in both cases, unless otherwise expressly stated, the stated threshold voltage refers to the optical threshold and is for a relative contrast of 10% (V). 10 The saturation voltage refers to optical saturation and is expressed for a relative contrast of 90% (V). 90 The capacitive threshold voltage (V0) (also known as the Freedericks threshold voltage) is expressed as such. Fr Use only when explicitly mentioned.

[0953] Unless otherwise expressly stated, all parameter ranges indicated in this application include limits.

[0954] Different upper and lower limits indicated by different ranges of properties can be combined to produce other preferred ranges.

[0955] Unless otherwise expressly stated, the following conditions and definitions apply throughout this application. All concentrations are expressed as a weight percentage and relative to the corresponding whole mixture; all temperatures are expressed in degrees Celsius and all temperature differences are expressed as degree differences. All physical properties were determined according to "Merck Liquid Crystals, Physical Properties of Liquid Crystals", Status, November 1997, Merck KGaA, Germany, and unless otherwise expressly stated, are expressed relative to a temperature of 20°C. Optical anisotropy (Δn) was measured at a wavelength of 589.3 nm. Dielectric anisotropy (Δε) was measured 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 measure Δε had a cell thickness of approximately 20 μm. The electrodes were 1.13 cm thick. 2 Circular ITO electrodes with area and guard ring. The alignment layer is SE-1211 from Nissan Chemicals, Japan (for vertical alignment (ε)). || )) and polyimide AL-1054 from Japan Synthetic Rubber, Japan (for surface orientation (ε) ⊥ The capacitor used is a Solatron 1260 frequency response analyzer with a voltage of 0.3V. rmsThe voltage was measured using a sinusoidal wave. White light was used in the electro-optic measurement. The settings used here were those of a DMS instrument commercially available from Autronic-Melchers, Germany. The characteristic voltage was measured under vertical observation. The threshold voltage (V) was measured at 10%, 50%, and 90% relative contrast, respectively. 10 ), intermediate grayscale (V) 50 ) and saturation (V) 90 )Voltage.

[0956] In this application, unless otherwise expressly stated, the term compound means both one compound and multiple compounds.

[0957] 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. Here, "having a nematic phase" means, on the one hand, that no smectic phase or crystallization is observed at the corresponding low temperature, and on the other hand, that the nematic phase does not become clear upon heating. At high temperatures, the clearing point is measured in a capillary using conventional methods. Low-temperature studies are performed in a flow cytometer at the corresponding temperature and checked by storing bulk samples: the bulk storage stability (LTS) of the medium according to the invention at a given temperature T is determined by visual inspection. 2 g of the medium of interest is filled into a suitably sized closed glass container (bottle) placed in a freezer at a predetermined temperature. The bottle is checked at defined time intervals for the appearance of a smectic phase 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 appearance of a higher ordered phase is recorded as the corresponding storage stability. The test is finally terminated after 1000 h, i.e., an LTS value of 1000 h means that the mixture is stable at a given temperature for at least 1000 h.

[0958] The liquid crystal medium according to the invention may contain other additives and chiral dopants at conventional concentrations. Based on the overall mixture, the total concentration of these other components ranges from 0% to 10%, preferably from 0.1% to 6%. The concentration of each individual compound used is preferably in the range of 0.1% to 3%. In this application, the concentrations of these and similar additives are not taken into account when representing the concentration values ​​and ranges of the liquid crystal components and liquid crystal compounds in the liquid crystal medium.

[0959] Preferably, the medium according to the invention contains one or more chiral compounds as chiral dopants to adjust their cholesterol pitch. Their total concentration 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%.

[0960] 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 of the invention is preferably 0% to 30%, more preferably 0.1% to 20%, and most preferably 1% to 15%.

[0961] The response times are given as follows: rise time (τ) 接通 ), which are respectively tuned to relative contrast from 0% to 90% (t) for electro-optic response. 90 The change time of -t0) includes the delay time (t 10 -t0); decay time (τ) 断开 ), which is the relative contrast tuning of the electro-optic response from 100% to 10% (t) 100 To t 10 The time of change of ) and the total reaction time (τ) 总 =τ 接通 +τ 断开 ).

[0962] The liquid crystal medium according to the invention comprises a variety of compounds, preferably 3 to 30, more preferably 4 to 20, and most preferably 4 to 16 compounds. These compounds are mixed in a conventional manner. Generally, 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, for example using a so-called premix, which may be, for example, a homologous or eutectic mixture of compounds, or using a so-called "multi-bottle" system, the components of which are themselves ready-to-use mixtures.

[0963] All temperatures (e.g., the melting point of liquid crystals T(C,N) or T(C,S), the transition temperature from smectic (S) phase to nematic (N) phase T(S,N), and the clearing point T(N,I)) are expressed in degrees Celsius. All temperature differences are expressed in degrees.

[0964] 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 abbreviated 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 2lThe symbols represent straight-chain alkyl or alkylene groups, each having n, m, and l C atoms, 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 ring elements used in the core structure of the compound, 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 the illustrative structures of the compounds and their corresponding abbreviations.

[0965] Table A: Ring Elements

[0966]

[0967]

[0968]

[0969]

[0970]

[0971] Table B: Linking Groups

[0972] Table B: End bases

[0973]

[0974] Where n and m each represent integers, and the three dots "..." are placeholders for other abbreviations from the table.

[0975] The table below shows illustrative structures and their corresponding abbreviations. These structures are shown to explain the meaning of the abbreviation rules. They also represent compounds that are preferred for use.

[0976] Table C: Explanatory Structure

[0977] The following illustrative structures are compounds that are preferred for use in the medium:

[0978]

[0979]

[0980]

[0981]

[0982]

[0983]

[0984]

[0985]

[0986]

[0987]

[0988]

[0989]

[0990]

[0991] Where m and n are the same or different and are 1, 2, 3, 4, 5, 6 or 7.

[0992] Preferably, the medium according to the invention comprises one or more compounds selected from the compounds in Table C.

[0993] The table below (Table D) shows illustrative compounds that can be used as alternative stabilizers in the mesocrystalline media according to the invention. The total concentration of these and similar compounds in the media is preferably 5% or less.

[0994] Table D

[0995]

[0996]

[0997]

[0998] In a preferred embodiment of the invention, the mesocrystalline medium comprises one or more compounds selected from Table D.

[0999] The following table (Table E) shows illustrative compounds that are preferably used as chiral dopants in mesocrystalline media according to the invention.

[1000] Table E

[1001]

[1002]

[1003]

[1004] In a preferred embodiment of the invention, the mesocrystalline medium comprises one or more compounds selected from Table E.

[1005] The mesocrystalline medium according to this application preferably comprises two or more, preferably four or more, compounds selected from the tables above.

[1006] Without further elaboration, it is believed that those skilled in the art can utilize the invention to its fullest extent using the foregoing description. Therefore, the following embodiments should be interpreted as merely illustrative and not as limiting the remainder of the invention in any way. From the specification, those skilled in the art can readily identify the essential features of the invention, and various modifications and alterations can be made to adapt it to various uses and conditions without departing from its spirit and scope. Example

[1007] The comparative mixture C1 and example mixtures N1-N22 used in this invention, having the compositions and properties shown in the table below, were prepared and characterized according to their general physical properties and their suitability in optical components.

[1008] An optical component, comprising a medium as defined herein and manufactured according to a method as defined herein, is characterized by excellent operational stability when exposed to the environment due to the high brightness temperature, wide nematic phase range, and excellent low-temperature stability (LTS) of the liquid crystal medium used therein. Therefore, the component and devices comprising it can operate under extreme temperature conditions. Surprisingly, the temperature dependence of the birefringence of the liquid crystal medium is very small, i.e., Δn changes very little with temperature, which makes the device reliable and easy to control.

[1009] Comparison of mixture C1

[1010]

[1011]

[1012] Example N1

[1013]

[1014] Example N2

[1015]

[1016]

[1017] The birefringence of mixture C-1 and mixture examples N-1 and N-2 was measured and compared at 20°C and 60°C. The results are shown in Table 1.

[1018] Table 1:

[1019] mixture <![CDATA[Δn 20 ]]> <![CDATA[Δn 60 ]]> <![CDATA[Δn 20 / Δn 60 ]]> C-1 0.2939 0.2511 1.170 N-2 0.3838 0.3538 1.085 N-3 0.4267 0.3951 1.080

[1020] Surprisingly, for the medium according to the invention, the ratio Δn 20 / Δn 60 Advantageously, they are smaller, meaning they exhibit a smaller birefringence variation with temperature compared to existing media.

[1021] Example N3

[1022]

[1023]

[1024] Example N4

[1025]

[1026] Example N5

[1027]

[1028]

[1029] Example N6

[1030]

[1031] Example N7

[1032]

[1033] Example N8

[1034]

[1035] Example N9

[1036]

[1037] Example N10

[1038]

[1039]

[1040] Example N11

[1041]

[1042] Example N12

[1043]

[1044]

[1045] Example N13

[1046]

[1047] Example N14

[1048]

[1049] Example N15

[1050]

[1051]

[1052] Example N16

[1053]

[1054] Example N17

[1055]

[1056]

[1057] Example N18

[1058]

[1059] Example N19

[1060]

[1061] Example N20

[1062]

[1063] Example N21

[1064]

[1065] Example N22

[1066]

[1067] Furthermore, the media according to the present invention are characterized by a combination of high brightness temperature and excellent low-temperature stability, i.e., they have a very wide operating temperature range.

[1068] Furthermore, the medium according to the invention exhibits a surprisingly low threshold voltage V0.

[1069] Surprisingly, media containing compounds RO with alkoxy side chains have higher birefringence and higher clearing temperatures than media containing only compounds with alkyl side chains.

Claims

1. An optical component (100) capable of operating in the infrared region of the electromagnetic spectrum, comprising: The liquid crystal medium (140) sandwiched between the first substrate (110) and the second substrate (160) facing each other, First and second electrodes (120, 150) are used to provide a potential on the liquid crystal material so as to drive the liquid crystal in a predetermined configuration. Its features The liquid crystal medium comprises one or more compounds selected from formulas I, II, and III. in R 1 The symbol represents H, a straight-chain or branched alkyl group having 1 to 12 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 15 carbon atoms, wherein one or more CH2- groups may be... , , , or Replacement n is 0, 1, or 2. to Each occurrence is represented independently. Where R L Each time it appears, it represents H or an alkyl group having 1 to 6 carbon atoms, and in which Alternative representation R 2 The symbol represents H, a straight-chain or branched alkyl group having 1 to 12 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 15 carbon atoms, wherein one or more CH2- groups may be... , , , or Replacement Z 21 This means -C≡C-, and express Where R L Each time it appears, it represents H or an alkyl group having 1 to 6 carbon atoms, and in which express , where R L H represents And among them R 3 The symbol represents H, a straight-chain or branched alkyl group having 1 to 12 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 15 carbon atoms, wherein one or more CH2- groups may be... , , , or Replacement Z 31 and Z 32 One of them means trans- CH=CH-, trans- CF = CF- or -C ≡ C- and another independent of it is represented as -C ≡ C-. trans- CH=CH-, trans- CF = CF- or single bond, to Representing each other independently Where R L Each time it appears, it represents H or an alkyl group having 1 to 6 carbon atoms, and in which Alternative representation The liquid crystal medium contains one or more compounds selected from formulas RO-1 to RO-7. Where X 1 and X 2 Indicates H or F, R RO This refers to a straight-chain or branched alkyl group having 1 to 12 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 12 carbon atoms, wherein one or more CH2- groups in each group may be... , , , or Replacement Z T1 Z T2 The same or different representations of -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, or single bonds, X 1 X 2 X 3 and X 4 They may represent H, Cl, F, or CH3 in the same or different ways. t is 0 or 1, and and It indicates that it is selected from the following groups: a) 1,4-Phenylidene, wherein one or both CH groups may be substituted with N, and one or more H atoms may be substituted with L. L, in each occurrence, may refer to F, Cl, or a straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy group having 1 to 12 carbon atoms, optionally fluorinated in each case; and The liquid crystal medium comprises one or more compounds of formula III-1b. R 3 The symbol represents H, a straight-chain or branched alkyl group having 1 to 12 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 15 carbon atoms, wherein one or more CH2- groups may be... , , , or Replacement.

2. The optical component capable of operating in the infrared region of the electromagnetic spectrum according to claim 1, wherein the medium comprises one or more compounds of formula II-1c, one or more compounds of formula RO-2, and one or more compounds of formula III-1b. The meaning of each group is as defined in claim 1.

3. The optical component capable of operating in the infrared region of the electromagnetic spectrum according to claim 1, wherein the liquid crystal 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. L 4 and L 5 The same or different F, Cl or straight-chain or branched or cyclic alkyl or alkenyl groups each having up to 12 C atoms; Z T3 Z T4 They may represent -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C- or single bonds, and the same or different. t is 0 or 1.

4. The optical component capable of operating in the infrared region of the electromagnetic spectrum according to claim 1 or 2, wherein the liquid crystal medium is a polymer network liquid crystal, the polymer network liquid crystal comprising a polymer network obtainable by in-situ polymerization of the liquid crystal medium according to claim 1, the liquid crystal medium further comprising one or more compounds of formula P. P a -(Sp a ) s1 -A 2 -(Z a -A 1 ) n2 -(Sp b ) s2 -P b P Each of the groups has the following meaning: P a P b Each of them independently represents a polymerizable group. Sp a Sp b The spacer group may be represented the same or different each time it appears. s1 and s2 each represent 0 or 1 independently. A 1 A 2 Each group independently represents a group selected from the following groups: a) The group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, and 4,4'-bicyclohexylene, 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. b) The group consisting of 1,4-phenylene and 1,3-phenylene, wherein one or both CH groups may be substituted with N, and one or more H atoms may be substituted with L. c) The group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl, and selenophenol-2,5-diyl, each of which may be mono- or poly-substituted by L. d) The group consisting of polycyclic groups that are saturated, partially unsaturated, or fully unsaturated and optionally substituted, having 5 to 20 ring carbon atoms, one or more of which may be substituted by heteroatoms. n2 represents 0, 1, 2, or 3. Z a In each case, it can be represented independently as -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2). n -, where n is 2, 3, or 4, -O-, -CO-, -C(R) y R z -, -CH2CF2-, -CF2CF2- or a single bond, L, appearing repeatedly or differently, represents F, Cl, CN, SCN, SF5, or a straight or branched chain having 1 to 12 C atoms, and in each case, optionally a fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy. R y R z Each of these terms independently represents H, F, or a straight-chain or branched alkyl group having 1 to 12 carbon atoms, wherein one or more H atoms may be replaced by F. M represents -O-, -S-, -CH2-, -CHY 1 -or-CY 1 Y 2 -,and Y 1 and Y 2 Each of these can independently represent H, F, or a straight-chain or branched alkyl group having 1 to 12 C atoms, wherein one or more H atoms may be replaced by F, or represent Cl or CN.

5. The optical component capable of operating in the infrared region of the electromagnetic spectrum according to claim 1 or 2, wherein the liquid crystal medium comprises a chiral dopant.

6. The optical component that can operate in the infrared region of the electromagnetic spectrum according to claim 1 or 2, wherein the liquid crystal medium contains a stabilizer.

7. The optical component that can operate in the infrared region of the electromagnetic spectrum according to claim 1 or 2, wherein the component is a transmission spatial light modulator.

8. An optical component operable in the infrared region of the electromagnetic spectrum according to claim 1 or 2, wherein the component is a reflective spatial light modulator (100) configured to modulate the phase of an incident light signal propagating at least partially in a first dimension, wherein the first substrate is a transparent glass layer (110) having a first transparent electrode (120), and wherein the second substrate is a CMOS silicon substrate (160), the component further comprising a mirror (150) disposed between the second substrate and the liquid crystal medium (140), wherein the mirror is divided into a two-dimensional array of individually addressable pixels arranged and configured as second electrodes (150), each pixel being individually driven by a voltage signal to provide a local phase change to at least one polarization component of the light signal.

9. An LCoS device, characterized in that... It includes the optical components that can operate in the infrared region of the electromagnetic spectrum as described in claim 8.

10. A device comprising the LCoS device of claim 9, wherein the device is a wavelength selective switch, a LiDAR scanner, an infrared scene projector, a wavelength division multiplexing system, a reconfigurable optical add-drop multiplexer, or an electroevanescent optical refractive prism.

11. A method for spatially modulating infrared light, the method comprising: i) Provide an optical assembly comprising first and second substrates facing each other and each having a surface, the first substrate comprising at least one first electrode, the second substrate comprising at least one second electrode, the assembly further comprising a liquid crystal layer sandwiched between the first and second substrates, wherein the liquid crystal comprises one or more compounds selected from the compounds of claim 1. ii) Receive incident infrared light on the surface of the optical component; iii) Apply a predetermined voltage to each electrode formed on the first substrate to modulate the refractive index of the liquid crystal layer.

12. A method for manufacturing an optical phase modulator, comprising at least the following steps: a) Provide a first substrate having a first electrode, the first electrode optionally having a two-dimensional array of individually electrically drivable units; b) Depositing the liquid crystal medium as described in claim 1 on the first substrate; and c) Mount a second substrate having a second electrode onto the liquid crystal material.

13. A liquid crystal medium comprising one or more compounds selected from formulas I, II and III as defined in claim 1, and one or more compounds selected from formulas RO-1 to RO-7, and a compound of formula III-1b.

14. The liquid crystal medium according to claim 13, wherein the medium comprises one or more compounds of formula II-1c, one or more compounds of formula RO-2, and one or more compounds of formula III-1b. The meaning of each group is as defined in claim 1.

15. The medium according to claim 14, wherein R RO Indicates cycloalkyl.

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