LCD Media

Abstract

A liquid crystal medium for use in liquid crystal-on-silicon (LCoS) displays is provided. 【Solution】A liquid crystal medium having negative dielectric anisotropy, comprising a compound of the following formula (I). TIFF2026167501000285.tif42166 (In the formula, R 11 and R 12 are identical or different, and represent H, linear alkyl or alkoxy each having 1 to 15 C atoms, linear alkenyl or alkenyloxy each having 2 to 15 C atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy each having 3 to 15 C atoms, etc., L 11 , L 12 , L 13 , L 14 are identical or different and represent H, F, Cl, CH₃, CF₃ or CHF₂, and at least one of L 11 , L 12 , L 13 , L 14 represents F, Cl, CH₃, CF₃, or CHF₂.)

Description

[Technical Field]

[0001] The present invention relates to liquid crystal (LC) media having negative dielectric anisotropy, and their use in optical, electro-optical and electronic applications, particularly in liquid crystal displays. The present invention further relates to liquid crystal on silicon (LCoS) displays, comprising the LC media, for use in electronic components that can operate in the visible (VIS) or infrared (IR) region of the electromagnetic spectrum, such as VAs in IPS or FFS displays, or in devices such as augmented reality eyewear, smart glasses, virtual reality headsets, head-up display systems, head-mounted displays, or near-to-eye displays. [Background technology]

[0002] Liquid crystal media have been used for many years in electro-optical displays (liquid crystal displays: LCDs) to display information by amplitude modulation of polarization in the visible region, and are widely used in televisions, monitors, and displays for portable devices such as tablet PCs and mobile phones.

[0003] Nematic liquid crystals have also been proposed for optical phase modulation. The paper, *Optical phased array technology*, Proc IEEE, 1996; Vol. 84: pp. 268-298; doi: 10.1109 / 5.482231, by McManamon PF, Dorschner TA, Corkum DL, Friedman LJ, Hobbs DS, Holz M, Liberman S, Nguyen HQ, Resler DP, Sharp RC, and Watson EA, describes liquid crystal optical phased arrays for various types of sensor applications. The paper, "Liquid crystal waveguides: new devices enabled by >1000 waves of optical phase control," by Scott R. Davis, George Farca, Scott D. Rommel, Seth Johnson, and Michael H. Anderson, Proc. SPIE7618, Emerging Liquid Crystal Technologies V, No. 76180E (February 12, 2010); doi:10.1117 / 12.851788, describes refractive beam control using waveguide structures.

[0004] LCoS is a small, reflective, active-matrix liquid crystal display, or "microdisplay," that uses the top liquid crystal layer on a silicon backing plate. It is also known as a spatial light modulator (SLM).

[0005] The silicon backplate is an array of pixels, each having a mirror surface and simultaneously functioning as a conductor. Each pixel contains a stationary mirror covered with an active liquid crystal layer having a twisted nematic orientation that can be switched to a homeotropic orientation by the application of voltage. LCoS microdisplays are typically small, with a diagonal of less than 1.0 inch, but can achieve high resolutions from 1 / 4 VGA (78,000 pixels) to UXGA+ (over 2 million pixels).

[0006] Due to the small size of the pixels, and because LCoS displays also have very small cell thicknesses, typically around 1 micron, a low cell thickness may also be required when the device operates in reflective mode, as light passes through the LC layer twice. Therefore, the liquid crystal phase used in these displays must have a particularly high optical anisotropy Δn, in contrast to conventional reflective LC displays, which typically require an LC phase with a low Δn. Since the response time is proportional to the cell thickness and often proportional to its square (decreasing quadratically), small cell thicknesses are preferred, especially in applications requiring very short response times.

[0007] Liquid crystal compounds with high birefringence often possess an intrinsic smectic phase, or when mixed with other liquid crystal compounds, they induce the formation of a smectic phase, which adversely affects the low-temperature stability of displays.

[0008] Initially developed for projection televisions, LCoS is now also used in wavelength-selective switches, structural illumination, near-eye displays, and light pulse shaping. Its ability to produce high-quality images with excellent contrast and color reproduction makes it particularly valuable in environments where image fidelity is critical. Computer-generated holograms may be encoded on a spatial light modulator positioned to modulate the amplitude and / or phase of incident light, forming part of a hologram projector as described in International Publication No. 2020 / 015933. Such projectors have found applications in head-up displays (HUDs) and head-mounted displays (HMDs) encompassing near-eye devices.

[0009] The rapid advancements in augmented reality (AR) and virtual reality (VR) technologies are driving demand for high-performance display systems that can deliver immersive and interactive visual experiences. Devices such as AR eyewear, smart glasses, and VR headsets heavily rely on the quality and efficiency of display components to overlay digital information onto the real world or to construct fully virtual environments.

[0010] Another application of liquid crystal devices is LiDAR (light detection and ranging), a method of measuring distance by shining laser light onto a target and measuring the reflection with a sensor. Therefore, differences in laser reflection time and wavelength can be used to create a digital three-dimensional representation of the target. International Publication No. 2019 / 24052 proposes, for example, a holographic LiDAR system using LCoS SLM.

[0011] One of the most important features of phase-dedicated LCoS devices is the use of optically nonlinear liquid crystal materials that are sensitive to operating temperature. While conventional LCoS devices primarily rely on light intensity modulation, which is less affected by temperature changes, in phase-dedicated LCoS devices, the optical phase modulation of the incident light is an essential performance parameter and can be easily affected by even slight changes in operating temperature, resulting in significant changes in the output of the corresponding optical diffraction.

[0012] Another significant challenge in the development of next-generation LCoS devices is the creation of high-speed multilevel phase modulation. While nematic LCoS devices offer the advantages of multilevel phase modulation, they are constrained by the slow response speed of nematic LCs. This is especially true for communications applications requiring thicker devices using infrared wavelengths, thus further reducing response speed. Therefore, the main material challenge in these applications is finding suitable high-speed LC materials that can achieve the full 2π phase depth required in these applications.

[0013] In projection displays using LCoS, the light source is relatively bright, and the liquid crystal is exposed to high-intensity light for extended periods. This prolonged exposure to high-intensity light, especially ultraviolet light and high-energy visible light (blue light), can cause photodegradation of the liquid crystal material. Furthermore, high-intensity light sources can generate significant heat, which can exacerbate the effects of photodegradation.

[0014] Therefore, there is a need for liquid crystal-based optical components, particularly LCoS devices, that operate in the visible or infrared region of the electromagnetic spectrum, possessing high birefringence and fast switching speeds, and offering improved overall application-related characteristics.

[0015] In particular, there is a need in this field for high-performance liquid crystal materials that can maintain stability under various operating conditions, including long-term light exposure.

[0016] Furthermore, so-called VA ("Vertical Alignment") displays, which have a wider viewing angle, are known. The LC cells of a VA display contain a layer of LC medium between two transparent electrodes, where the LC medium typically has negative dielectric anisotropy. In the switched-off state, the molecules in the LC layer are either aligned perpendicularly (homeotropically) to the electrode surface or have a tilted homeotropic arrangement. When a voltage is applied to the two electrodes, a rearrangement of the LC molecules parallel to the electrode surface occurs.

[0017] So-called IPS ("in-plane switching") displays are also known, which contain an LC layer between two substrates, where two electrodes are located on only one of the two substrates, preferably having an interlocking comb-like structure. When a voltage is applied to the electrodes, an electric field with a significant component parallel to the LC layer is generated between the electrodes. This causes a rearrangement of LC molecules within the layer plane.

[0018] Furthermore, so-called FFS ("Fringe Field Switching") displays have been reported (see, in particular, SHJung et al., Jpn.J.Appl.Phys., Volume 43, No.3, 2004, 1028), which contain two electrodes on the same substrate, one structured in a comb-like manner and the other unstructured. A strong, so-called "fringe field," i.e., a strong electric field near the edge of the electrode, is generated thereby, and an electric field with both strong vertical and strong horizontal components is generated throughout the cell. FFS displays have low viewing angle dependence of contrast. FFS displays typically include an LC medium with positive dielectric anisotropy and an array layer, usually polyimide, which gives a planar alignment to the molecules of the LC medium.

[0019] FFS displays can operate as either active-matrix or passive-matrix displays. In active-matrix displays, individual pixels are typically addressed by integrated nonlinear active elements, such as transistors (e.g., thin-film transistors ("TFTs")), while in passive-matrix displays, individual pixels are typically addressed by multiplexing methods known from the prior art.

[0020] Furthermore, FFS displays have been disclosed (see SHLee et al., Appl. Phys. Lett. 73(20), 1998, 2882-2883 and SHLee et al., Liquid Crystals 39(9), 2012, 1141-1148), which have a similar electrode design and layer thickness to FFS displays, but include a layer of LC medium with negative dielectric anisotropy instead of LC medium with positive dielectric anisotropy. LC medium with negative dielectric anisotropy exhibits a more preferred waveguide orientation with less tilt and greater torsion compared to LC medium with positive dielectric anisotropy, and as a result, these displays have higher transmittance. The display further includes an array layer, preferably polyimide, provided on at least one of the substrates, which is in contact with the LC medium and induces a planar alignment of LC molecules in the LC medium. These displays are also called "ultrabrightness FFS (UB-FFS)" mode displays. These displays require a reliable LC medium.

[0021] In more recent types of VA displays, the uniform orientation of LC molecules is limited to a number of relatively small domains within the LC cell. Discrinciple may exist between these domains, also known as tilt domains. VA displays with tilt domains have a wider, contrast-independent viewing angle and more intermediate tones compared to conventional VA displays. In addition, this type of display is easier to manufacture and no longer requires further treatment of the electrode surface, such as rubbing, to uniformly orient molecules when switched on. Instead, the preferred direction of the tilt angle or pre-tilt angle is controlled by a special design of the electrodes.

[0022] In so-called MVA ("Multi-Domain Vertical Alignment") displays, this is typically achieved by electrodes with protrusions, which causes localized pre-tilt. As a result, when voltage is applied, LC molecules are oriented parallel to the electrode surface in various directions and in various specified areas of the cell. This achieves "controlled" switching and prevents the formation of coherent disclination lines. While this arrangement improves the viewing angle of the display, it results in reduced light transmittance. Further development of MVA involves using protrusions on only one electrode side, while the opposite electrode has a slit, thereby improving light transmittance. The slitted electrode generates a non-uniform electric field within the LC cell when voltage is applied, which means that controlled switching is still achieved. The distance between the slit and the protrusion can be increased to further improve light transmittance, but this results in a longer response time. In so-called PVA ("patterned VA") displays, the protrusions are completely superfluous, with both electrodes structured by slits on opposite sides. This results in increased contrast and improved light transmission, but it is technically difficult, and the display becomes more sensitive to mechanical influences (such as "tapping"). However, many applications, such as monitors, especially television screens, require faster response times and improved contrast and brightness (transparency) of the display.

[0023] Further developments include so-called PS ("polymer-maintained") or PSA ("polymer-maintained orientation") type displays, sometimes referred to as "polymer-stabilized." In these displays, a small amount (e.g., 0.3% by weight, typically less than 1% by mass) of one or more polymerizable compounds, preferably polymerizable monomer compounds, is added to the LC medium. After filling the display with the LC medium, it is polymerized or crosslinked in situ, usually by ultraviolet photopolymerization, optionally while applying a voltage to the display electrodes. This polymerization is carried out at a temperature at which the LC medium exhibits a liquid crystal phase, usually at room temperature. Adding polymerizable mesogens or liquid crystal compounds, also known as reactive mesogens or "RM," to the LC mixture has proven particularly appropriate.

[0024] On the other hand, the PS(A) principle is used in various conventional liquid crystal display modes. For example, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, and PS-TN displays are known. Polymerization of RM is preferably carried out with voltage applied in the case of PS-VA and PS-OCB displays, and with or without voltage applied, preferably without charge, in the case of PS-IPS displays. As can be demonstrated in test cells, the PS(A) method results in pre-tilt within the cell. In the case of PS-VA displays, pre-tilt has a positive effect on response time. For PS-VA displays, standard MVA or PVA pixel and electrode layouts can be used. However, it is also possible to use a design without protrusions, for example, on one electrode side that is structured only, which significantly simplifies manufacturing and at the same time results in very good contrast and very good light transmittance.

[0025] PS-VA displays are described, for example, in European Patent Publication No. 1170626, U.S. Patent No. 6,861,107, U.S. Patent No. 7,169,449, U.S. Patent Publication No. 2004 / 0191428, U.S. Patent Publication No. 2006 / 0066793, and U.S. Patent Publication No. 2006 / 0103804.

[0026] Especially for monitors, and particularly television applications, optimization of liquid crystal display response time, as well as contrast and brightness (and therefore transmittance), continues to be required. Here, the PSA method can offer significant advantages. In particular, for PS-VA, PS-IPS, and PS-FFS displays, it is possible to achieve a reduction in response time correlated with measurable pre-tilt in the test cell without significant adverse effects on other parameters.

[0027] Another problem observed in prior art was that, when conventional LC media were used in LC displays, including but not limited to PSA-type displays, unevenness often occurred in the display, especially when the LC media was filled into display cells manufactured using the one-drop filling (ODF) method. This phenomenon is also known as "ODF unevenness." Therefore, it is desirable to provide an LC media that leads to a reduction in ODF unevenness.

[0028] Another problem observed in the prior art is that LC media for use in PSA displays, including but not limited to PSA-type displays, often exhibit high viscosity, resulting in long switching times. To reduce the viscosity and switching time of the LC media, the prior art has suggested adding LC compounds containing alkenyl groups. However, LC media containing alkenyl compounds have often been observed to exhibit reduced reliability and stability, as well as a decrease in VHR, particularly after exposure to UV radiation. In particular, since the photopolymerization of RM in PSA displays is usually carried out by exposure to UV radiation, this can cause a decrease in VHR in the LC media, which is quite unfavorable for use in PSA displays.

[0029] In addition, there is a great demand for PSA displays, and for LC media and polymerizable compounds used in such PSA displays, which enable a wide operating temperature range, high resistivity, short response time even at low temperatures, and low threshold voltage, low pre-tilt angle, numerous intermediate tones, high contrast and wide viewing angles, high reliability and high VHR after UV exposure, and, in the case of polymerizable compounds, low melting point and high solubility in LC host mixtures. For mobile applications, the availability of LC media exhibiting low threshold voltage and high birefringence is particularly desirable for PSA displays.

[0030] One of the trends in displays is achieving the fastest possible response time to obtain the best video quality. In this respect, media with negative dielectric anisotropy are inherently at a disadvantage compared to LC media with positive dielectric anisotropy. On the other hand, mixtures with negative dielectric anisotropy enable high transmittance in standard FFS cell layouts, so their use has a positive impact on power consumption and the environment. In this field, it is necessary to achieve both fast response time and higher transmittance. There is a great demand for displays with high transmittance, especially for use in mobile devices, which allows for the use of lower intensity backlights, thus leading to longer battery life and thus more sustainable products. Alternatively, it may be possible to achieve displays with improved contrast and higher brightness, especially in ambient light. Furthermore, the popularity of 8K and gaming monitors has led to an increased demand for LC display panels with higher refresh rates and thus for LC media with faster response times.

[0031] Another important trend in displays is achieving a high contrast ratio. The contrast ratio is described as the ratio of the light and dark states of a display. In particular, in LCDs using IPS / FFS technology, the dark state is strongly affected by scattering parameters, thus significantly impacting the contrast ratio. Improving the contrast ratio and reducing scattering parameters requires LC mixtures with high elastic constants. However, current LC single materials and LC mixtures have limitations in achieving very high elastic constants. Therefore, to further increase the contrast ratio of future displays, new materials will need to be discovered.

[0032] Therefore, there remains a great demand for VA, FFS, or PSA displays that do not exhibit the above-mentioned drawbacks, or exhibit only minor drawbacks, and have improved properties, as well as for LC media that may contain polymerizable compounds for use in VA, FFS, or PSA displays. [Overview of the project] PROBLEMS TO BE SOLVED BY THE INVENTION

[0033] The present invention has been devised in view of the problems of the prior art described in the present specification. Accordingly, an object of the present invention is to provide a novel and useful liquid crystal material, device, and technique that solve the problems described in the present specification. MEANS FOR SOLVING THE PROBLEMS

[0034] The present invention relates to a liquid crystal medium comprising one or more compounds of Formula I and having negative dielectric anisotropy.

[0035] CHEMICAL FORMULA (In the formula, R 11 and R 12 are identical or different, and represent H, linear alkyl or alkoxy each having 1 to 15 C atoms, linear alkenyl or alkenyloxy each having 2 to 15 C atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy each having 3 to 15 C atoms, wherein one or more CH₂ groups are, independently of each other, in a manner such that O atoms are not directly adjacent to each other

[0036] CHEMICAL FORMULA may each be substituted with -CH=CH-, -C≡C-, -CF₂O-, -OCF₂-, -O-, -CO-O- or -O-CO-, and one or more H atoms may be substituted with halogen, L 11 , L 12 , L 13 , L 14 are identical or different and represent H, F, Cl, CH₃, CF₃ or CHF₂, preferably H or F, and at least one of L 11 , L 12 , L 13 , L 14 represents F, Cl, CH₃, CF₃ or CHF₂, preferably F)

[0037] Preferably, the total concentration of the compound of formula I is in the range of 1% to 15%.

[0038] The medium preferably comprises one or more compounds selected from the group of compounds of formulas IIA, IIB, IIC, and IID.

[0039] [ka] (In the formula, R 2A , R 2B , R 2C and R 2D This represents a linear alkyl or alkoxy group having H, 1 to 15 carbon atoms, a linear alkenyl or alkenyloxy group having 2 to 15 carbon atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy group having 3 to 15 carbon atoms, where one or more CH2 groups in these groups are independent of each other and the oxygen atoms are not directly adjacent to each other.

[0040] [ka] -CH=CH-, -C≡C-, -CF2O-, -OCF2-, -O-, -CO-O-, or -O-CO- may be substituted, where one or more H atoms may be substituted with halogens. L 1 and L 2 These represent F, Cl, CF3, or CHF2 independently of each other. Y represents H, F, Cl, CF3, CHF2, or CH3, preferably H or CH3, more preferably H. Z 2 , Z 2B and Z 2D These independently represent a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, or -CH=CHCH2O-. X represents O or CH2, preferably CH2. (O) represents oxygen or a single bond. p represents 0, 1, or 2. q represents 0 or 1, (v represents an integer from 1 to 6)

[0041] Preferably, the total concentration of the compounds of formulas IIA, IIB, IIC, and IID is in the range of 10% to 60%.

[0042] According to another aspect of the present invention, an optoelectronic component comprising a liquid crystal medium according to the present invention is provided.

[0043] The present invention further relates to a device comprising the optoelectronic component, preferably an LCoS display.

[0044] The present invention further relates to liquid crystal displays comprising an LC medium according to the present invention, particularly VA, IPS, FFS or UB-FFS or PSA displays, and especially preferably FFS, UB-FFS, VA or PS-VA displays.

[0045] The present invention further relates to using the media defined above and below for phase modulation of the visible or infrared region of the electromagnetic spectrum, preferably the region from 420 nm to 750 nm, or the A band and / or B band and / or C band, for electro-optical purposes.

[0046] The present invention further relates to using the LC medium according to the present invention in a liquid crystal display.

[0047] The present invention further relates to a method for producing an LC medium, comprising the steps of mixing one or more compounds of formula I, preferably one or more compounds of formulas IIA, IIB, IIC and / or IID, optionally one or more chiral dopants, optionally one or more polymerizable compounds, and optionally further LC compounds and / or additives, as described above and below.

[0048] The present invention further relates to a method for manufacturing an LC display as described above and below, comprising the steps of filling or otherwise providing an LC medium containing one or more polymerizable compounds as described below between the substrates of the display, and optionally polymerizing the polymerizable compounds.

[0049] The medium of the present invention is characterized by very high birefringence, yet despite this high birefringence, excellent photostability is observed under blue light irradiation. Furthermore, this medium 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 switch, becomes very low. Low operating voltage and low threshold voltage are required to improve the switching characteristics of the device and achieve high energy efficiency. Low rotational viscosity enables high-speed switching of the components and devices according to the present invention.

[0050] The electronic components of the present invention are characterized by excellent operational stability under environmental exposure due to the high transparency temperature, wide nematic phase range, and excellent low-temperature stability (LTS) of the liquid crystal medium used. As a result, the components and devices containing them can operate even under extreme temperature conditions. Furthermore, the temperature dependence of the birefringence of the liquid crystal medium is very small, i.e., Δn hardly changes with temperature, resulting in high device reliability and ease of control.

[0051] The LC medium of the present invention exhibits remarkably high reliability and stability against ultraviolet light, backlight, and especially blue light, and at the same time possesses the following advantageous characteristics, particularly when used in LCoS displays. - Excellent low-temperature stability (LTS) - Improved contrast ratio of the display - High transparency of the display - High transparency - High voltage retention rate - Low rotational viscosity - High-speed switching - Fast response time enables low-power LCDs, extending the battery life of mobile devices. - High elastic constant.

[0052] Furthermore, the medium according to the present invention exhibits improved orientation on an inorganic orientation layer, such as a silicon oxide-based orientation layer. In particular, homeotropic orientation is maintained even at high temperatures ranging from room temperature to the transparency point of the medium.

[0053] A preferred synthetic route to the compound of formula I is shown in Scheme 1. Scheme 1: [ka] In the formula, X represents, for example, Br or I, and the other groups have the meanings shown in formula I above.

[0054] In this specification, alkyl or alkoxy groups mean linear, branched, or cyclic alkyl or alkoxy groups. Preferably linear, and preferably having 2, 3, 4, 5, 6, or 7 carbon atoms, and thus preferably representing ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, and further representing methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.

[0055] In this specification, the branched alkyl is preferably isopropyl, s-butyl, isobutyl, isopentyl, 2-methylbutyl, 2-methylhexyl, or 2-ethylhexyl.

[0056] As used herein, cyclic alkyl means a linear or branched alkyl or alkenyl having up to 12 carbon atoms, preferably an alkyl having 1 to 7 carbon atoms, where the CH2 group is substituted with a carbon ring having 3 to 5 carbon atoms, and is very preferably selected from the group consisting of cyclopropyl alkyl, cyclobutyl alkyl, cyclopentyl alkyl and cyclopentenyl alkyl, where the alkyl is a linear alkyl having 1 to 5 carbon atoms.

[0057] In this specification, oxaalkyl preferably represents linear 2-oxapropyl (=methoxymethyl), 2-(=ethoxymethyl) or 3-oxabutyl (=2-methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, or 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.

[0058] In this specification, alkenyls, i.e., alkyl groups in which one CH2 group is substituted with -CH=CH-, may be linear or branched. Preferably, they are linear and have 2 to 10 carbon atoms. Therefore, in part, these represent vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hexa-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl, octo-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, nona-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl, deca-1-, -2-, -3-, -4-, -5-, -6-, -7-, -8- or -9-enyl.

[0059] In this specification, the alkyl or alkenyl group, at least monosubstituted with a halogen, is preferably linear, and the halogen is preferably F or C, and very preferably F. In the case of polysubstituted groups, the halogen is preferably F. Examples of the resulting groups include perfluoro radicals. In the case of monosubstituted groups, the fluorine or chlorine substituent may be at any position, but is preferably at the ω position.

[0060] In this specification, the monofluorinated or polyfluorinated alkyl or alkoxy group having 1, 2, or 3 carbon atoms, or the monofluorinated or polyfluorinated alkenyl group having 2 or 3 carbon atoms, is particularly preferably F, Cl, CF3, CHF2, OCF3, OCHF2, OCFHCF3, OCFHCHF2, OCFHCHF2, OCF2CH3, OCF2CHF2, OCF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCFHCF2CF3, OCFHCF2CHF2, OCF2CF2CF3, OCF2CF2CClF2, OClFCF2CF3, OCH=CF2, or CH=CF2, and very particularly preferably F or OCF3, and further preferably CF3, OCF=CF2, OCHF2, or OCH=CF2.

[0061] In the compound of formula I, preferably group L 11 , L 12 , L 13 , and L 14 One or two of these, more preferably one, represent F, and the remaining base L 11 , L 12 , L 13 , and L 14 This represents H.

[0062] The compound of formula I is preferably selected from the compounds of formulas I-1 to I-6, more preferably from the compounds of formulas I-1 to I-4, very preferably from the compounds of formulas I-1 and I-2, and particularly from the compounds of formula I-1.

[0063] [ka]

[0064] In the formula, R 11 and R 12 The terms in formula I represent the meaning defined above, preferably a linear alkyl or alkoxy having 1 to 9 carbon atoms, or a linear alkenyl having 2 to 9 carbon atoms, and one or more CH2 groups in these groups are independently of each other.

[0065] [ka] Each of these can be substituted, and very preferably represents a linear alkyl or linear alkenyl having 1 to 9 carbon atoms. The medium of the present invention particularly preferably comprises one or more compounds of formula I-1, preferably compounds selected from compounds of formulas I-1-1 to I-1-23.

[0066] [ka] [ka] [ka]

[0067] In the formula, R 12The above meaning applies to formula I, and its sub-formulas preferably represent methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octyloxy, n-nonyloxy, buto-3-en-1-yl, trans-pento-3-en-1-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclopropylmethoxy, cyclopentyloxy, or cyclopentylmethoxy.

[0068] Preferred compounds of formulas IIA, IIB, IIC, and IID are listed below. [ka]

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080] [ka] [ka] [ka]

[0081] In the formula, parameter a represents 1 or 2, alkyl and alkyl* each independently represent a linear alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl* each independently represent a linear alkenyl group having 2 to 6 carbon atoms, and (O) represents an oxygen atom or a single bond. alkenyl and alkenyl* preferably represent CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH-, or CH3-CH=CH-(CH2)2-.

[0082] Very preferred compounds of formula IID are selected from the following sub-formulae. ##CHEMICAL## ##CHEMICAL## ##CHEMICAL## ##CHEMICAL##

[0083] ##CHEMICAL##

[0084] In a preferred embodiment, the medium comprises one or more compounds of formula IID-10a. ##CHEMICAL## In the formula, the groups and parameters that are present have the meanings described above for formula IID, ##CHEMICAL## In the formula, r is 0, 1, 2, 3, 4, 5 or 6, and s is 1, 2 or 3.

[0085] Preferred compounds of formula IID-10a are compounds IID-10a-1 to IID-10a-14. ##CHEMICAL##

[0086] ##CHEMICAL##

[0087] Particularly preferred mixtures of the present invention comprise one or more compounds of the formulae IIA-2, IIA-8, IIA-10, IIA-16, IIA-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1, IID-4, and IID-10.

[0088] Preferred media of the present invention comprise at least one compound of the formula IIC-1.

[0089] ##STR1## In the formula, alkyl and alkyl* have the meanings described above.

[0090] In particular, the medium comprises one or more compounds of formula IIA-2 selected from the following sub-formulae. ##STR2##

[0091] Alternatively, preferably, in addition to the compounds of the formulae IIA-2-1 to IIA-2-5, the medium comprises one or more compounds of the formulae IIA-2a-1 to IIA-2a-5. ##STR3##

[0092] Further, the medium comprises one or more compounds of formula IIA-10 selected from the following sub-formulae. ##STR4##

[0093] Alternatively, preferably, in addition to the compounds of the formulae IIA-10-1 to IIA-10-5, the medium comprises one or more compounds of the formulae IIA-10a-1 to IIA-10a-5. ##STR5##

[0094] In particular, the medium contains one or more compounds of formula IIB-10 selected from the following sub-formulas. [ka]

[0095] Alternatively, preferably, in addition to the compounds of formulas IIB-10-1 to IIB-10-5, the medium contains one or more compounds of formulas IIB-10a-1 to IIB-10a-5. [ka]

[0096] Alternatively, preferably, in addition to the compound of formula IIC-1, the medium includes one or more compounds of formula IIC-1a-1 and IIC-1a-2. [ka] In the formula, alkyl represents a linear alkyl group having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms, and very preferably ethyl.

[0097] The medium of the present invention preferably contains one or more compounds of formula III. [ka] In the formula, R 31 and R 32 Each of these independently represents an alkyl or alkoxy group having H and 1 to 15 C atoms, and one or more CH2 groups of these groups are arranged such that the O atoms are not directly adjacent to each other. [ka] -CH=CH-, -C≡C-, -CF2O-, -OCF2-, -O-, -CO-O-, or -O-CO- may be substituted, and one or more H atoms may be substituted with halogens, preferably linear alkyls having 1 to 6 C atoms.

[0098] A 31 Each instance of these symbols represents, independently of each other, the following: a) A 1,4-cyclohexenylene or 1,4-cyclohexylene group, where one or two non-adjacent CH2 groups may be substituted with -O- or -S-. b) A 1,4-phenylene group, where one or two CH groups may be substituted with N, or c) A group selected from spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl, Groups a), b), and c) may be monosubstituted or polysubstituted with halogen atoms.

[0099] n represents 0, 1, or 2, preferably 0 or 1. Z 31 Each instance of these symbols independently represents -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. L 31 and L 32 Each of these independently represents F, Cl, CF3, or CHF2, preferably H or F, most preferably F. W represents either O or S.

[0100] The medium preferably contains one or more compounds of formula III in a total concentration ranging from 5% to 30%.

[0101] The compound of formula III is preferably selected from the compounds of formula III-1 and / or III-2. [ka] In the formula, the groups present have the same meaning as those given in Formula III above, preferably R 31 and R 32 Each of them independently represents a linear alkyl, alkenyl, or alkoxy group having up to 15 C atoms, more preferably one or both of them representing an alkoxy group, L 31 and L 32 Each of these preferably represents F.

[0102] Preferably, the compound of formula III-1 is selected from the group consisting of compounds of formulas III-1-1 to III-1-10, preferably compounds of formula III-1-6. [ka] [ka] In the formula, alkyl and alkyl* each independently represent a linear alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl* each independently represent a linear alkenyl group having 2 to 6 carbon atoms, and alkoxy and alkoxy* each independently represent a linear alkoxy group having 1 to 6 carbon atoms. 31 and L 32 Each of these independently represents either F or Cl, preferably both being F.

[0103] Preferably, the compound of formula III-2 is selected from the group consisting of compounds of formulas III-2-1 to III-2-10, preferably compounds of formula III-2-6. [ka] [ka] In the formula, alkyl and alkyl* each independently represent a linear alkyl group having 1 to 6 carbon atoms, alkenyl and alkenyl* each independently represent a linear alkenyl group having 2 to 6 carbon atoms, and alkoxy and alkoxy* each independently represent a linear alkoxy group having 1 to 6 carbon atoms, L 31 and L 32 Each of these independently represents either F or Cl, preferably both being F.

[0104] The medium optionally contains one or more compounds of formula IIIA-1 and / or IIIA-2. [ka]

[0105] In the formula, L 31 and L 32 This has the same meaning as shown in Equation III, where (O) represents O or a single bond. R IIIA This refers to an alkyl or alkenyl group having up to 7 carbon atoms, or the Cy-C group. m H 2m+1 - represents, m and n are the same or different, and are 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1. Cy represents an alicyclic group having 3, 4, or 5 ring atoms, which are optionally substituted with an alkyl or alkenyl group having up to 3 C atoms, or with a halogen or CN, preferably representing cyclopropyl, cyclobutyl, cyclopentyl, cyclopenta-1-enyl, cyclopenta-2-enyl, and cyclopenta-3-enyl.

[0106] The compounds of formula IIIA-1 and / or IIIA-2 are preferably included in the medium in place of, or in addition to, the compounds of formula III.

[0107] The following are highly preferred compounds of formulas IIIA-1 and IIIA-2: [ka] [ka] In the formula, alkoky is a linear alkoxy group having 1 to 6 C atoms, or -(CH2) n F represents (where n is 2, 3, 4, or 5), preferably C2H4F.

[0108] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formula III-3. [ka] In the formula, R 31 , R 32 -CH=CH-, -CF2O-, -OCF2-, -CH=CH [ka] The atoms may be optionally substituted with -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens.

[0109] The compound of formula III-3 is preferably selected from the group consisting of compounds of formula III-3-1 to III-3-10. [ka] [ka] In the formula, R 32represents an alkyl group having 1 to 7 C atoms, preferably ethyl, n-propyl or n-butyl, or cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl, or -(CH2) n F (where n is 2, 3, 4, or 5), preferably C2H4F.

[0110] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formulas III-4 to III-6, preferably III-5. [ka] In the formula, the parameter has the meaning described above, R 31 R preferably represents a linear alkyl group. 32 Preferably, each represents an alkoxy having 1 to 7 carbon atoms.

[0111] In a preferred embodiment, the medium contains one or more compounds of formula III, selected from the group consisting of compounds of formula III-7 to III-9, preferably compounds of formula III-8. [ka] In the formula, the parameter has the meaning described above, R 31 Preferably, R represents a linear alkyl group. 32 Preferably, each represents an alkoxy having 1 to 7 carbon atoms.

[0112] In a preferred embodiment, the medium comprises one or more compounds of formula IV. [ka] In the formula, R 41 This represents an alkyl group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, preferably an n-alkyl group, and particularly preferably having 2, 3, 4 or 5 carbon atoms. R 42This represents an alkyl group having 1 to 7 carbon atoms or an alkoxy group having 1 to 6 carbon atoms (both preferably having 2 to 5 carbon atoms), an alkenyl group having 2 to 7 carbon atoms (preferably having 2, 3, or 4 carbon atoms), more preferably a vinyl group or a 1-propenyl group, particularly a vinyl group.

[0113] The medium preferably contains one or more compounds of formula IV in a total concentration ranging from 5% to 25%.

[0114] The compound of formula IV is preferably selected from the group consisting of compounds of formulas IV-1 to IV-4. [ka] In the formula, alkyl and alkyl' independently represent alkyl having 1 to 7 carbon atoms, preferably 1 to 5 carbon atoms. Alkenyl represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 carbon atoms. 'alkenyl' represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 to 3 carbon atoms. "alkoxy" represents an alkoxy group having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms.

[0115] The compound of formula IV-1 is preferably selected from the group consisting of compounds of formulas IV-1-1 to IV-1-6. [ka]

[0116] The compound of formula IV-2 is preferably selected from the compounds of formulas IV-2-1 and IV-2-2. [ka]

[0117] The compound of formula IV-3 is preferably selected from the group consisting of compounds of formulas IV-3-1, IV-3-2, and IV-3-3. [ka] In the formula, alkyl has the meaning defined above.

[0118] The compounds of formulas IV-3-1, IV-3-2, and IV-3-3 are preferably selected from the following compounds. [ka]

[0119] More preferably, the medium of the present invention comprises a compound of formula IV-4, particularly a compound selected from the compounds of formulas IV-4-1 to IV-4-3. [ka]

[0120] The liquid crystal medium preferably further comprises one or more compounds of formula IVa. [ka] In the formula, R 41 and R 42 Each of these independently represents a linear alkyl, alkoxy, alkenyl, alkoxyalkyl, or alkoxy group having up to 12 carbon atoms. [ka] Z 4 These represent single bonds, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, and -CF=CF-.

[0121] Preferred compounds of formula IVa are listed below. [ka] In the formula, alkyl and alkyl* each independently represent a linear alkyl group having 1 to 6 carbon atoms.

[0122] The medium preferably contains one or more compounds of formula IVa in a total concentration ranging from 1% to 10%.

[0123] The medium of the present invention preferably comprises at least one compound of formula IVa-1 and / or formula IVa-2.

[0124] The proportion of the compound of formula IVa in the whole mixture is preferably less than 5% by weight, and very preferably less than 2% by weight.

[0125] Preferably, the medium contains one or more compounds of formula IVb-1 to IVb-5, more preferably compounds of formula IVb-1 to IVb-3. [ka] In the formula, alkyl and alkyl* each independently represent a linear alkyl group having 1 to 6 carbon atoms. Alkenyl and alkenyl* each independently represent a linear alkenyl group having 2 to 6 carbon atoms. Of the compounds of formulas IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred. The following compounds of formula IVb are particularly preferred: [ka] In the formula, alkyl* represents an alkyl group having 1 to 6 carbon atoms, preferably n-propyl. The medium of the present invention particularly preferably comprises one or more compounds of formula IVb-1-1 and / or IVb-2-3.

[0126] The medium preferably contains one or more compounds of formula IVb-1 to IVb-5 in a total concentration ranging from 1% to 10%.

[0127] In a preferred embodiment, the medium of the present invention comprises one or more compounds of formula V. [ka] During the ceremony, R 51 , R 52 This represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkoxyalkyl group having 2 to 7 carbon atoms, an alkenyl group, or an alkenyloxy group. [ka] Z 51 , Z 52 Each of these independently represents -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond. n is either 1 or 2. Compounds of formulas CL and I are excluded.

[0128] The medium preferably contains one or more compounds of formula V in a total concentration ranging from 3% to 30%.

[0129] The compound of formula V is preferably selected from the compounds of formulas V-1, V-2, V-3, and V-4. [ka] The bases appearing in the formula have the meanings given in formula V above. The compound of formula V-1 is preferably selected from the compounds of formulas V-1-1 to V-1-8; The compound of formula V-2 is preferably selected from the compounds of formulas V-2-1 to V-2-4; The compound of formula V-3 is preferably selected from the compounds of formulas V-3-1 to V-3-5; The compound of formula V-4 is preferably selected from the compounds of formula V-4-1. [ka] [ka]

[0130] [ka] In the formula, R 51 and R 52 This has the meaning given by equation V above. R 51 and R 52 Preferably, each represents, independently of the others, a linear alkyl group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0131] A highly preferred compound of formula V-2-1 is selected from the compounds of formula V-2-1a to V-2-1g. [ka]

[0132] A highly preferred compound of formula V-2-2 is selected from the compounds of formulas V-2-2a to V-2-2i. [ka]

[0133] Preferably, the medium of the present invention comprises one or more compounds of formula CL. [ka] In the formula, R L H represents a linear or branched alkyl or alkoxy group having 1 to 15 carbon atoms, or a linear or branched alkenyl group having 2 to 15 carbon atoms, and one or more CH2 groups of these groups are independent of each other and in a manner in which the oxygen atoms are not directly adjacent to each other. [ka] The atoms may be substituted with -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens. X L represents F, Cl, CN, CHF2, CF3, OCF3, or is the same or different, R L It has one of the meanings, Y L1 and Y L2 These are identical or different elements, representing H, F, Cl, or CH3.

[0134] The medium preferably contains one or more compounds of formula CL in a total concentration ranging from 0.5% to 5%.

[0135] The compound of formula CL is preferably selected from the group of compounds of formulas CL-1, CL-2, CL-3, and CL-4. [ka] In the formula, R L1 and R L2 These are identical or different, and have the meanings described above for formula I, preferably representing an alkyl or alkenyl having 1 to 7 carbon atoms or 2 to 7 carbon atoms, where the CH2 group may be substituted with cyclopropane-1,2-diyl, or R L2 This represents an alkoxy having 1 to 5 carbon atoms.

[0136] A highly preferred compound of formula CL is selected from the compounds of formulas CL-3-1 to CL-3-12. [ka]

[0137] [ka]

[0138] In a particularly preferred embodiment, the medium of the present invention comprises the compound CL-3-1 or CL-3-3. Even more highly preferred are compounds of the formula CL-4, in particular wherein R L represents pentyl.

[0139] In a preferred embodiment of the present invention, the medium further comprises one or more compounds of the formula VI.

Chemical formula

Chemical formula

[0140] The medium preferably contains one or more compounds of formula VI in a total concentration ranging from 1% to 25%. The compound of formula VI is preferably selected from formulas VI-1 and VI-2. [ka] In the formula, the existing bases have the meaning given to formula VI.

[0141] The compound of formula VI-1 is preferably selected from formulas VI-1-1 to VI-1-22, and very preferably formula VI-1-4. [ka]

[0142] [ka]

[0143] [ka]

[0144] In the formula, R 6 (O) represents a linear alkyl or alkoxy group having 1 to 6 C atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5 or 6, n is 0, 1, 2, 3 or 4, and R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0145] In the compound of formula VI-1-4, (O) preferably represents -O-.

[0146] The compound of formula VI-2 is preferably selected from formulas VI-2-1 to VI-2-15, and very preferably formula VI-2-1. [ka]

[0147] [ka] In the formula, R 6 (O) represents a linear alkyl or alkoxy group having 1 to 6 C atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5 or 6, n is 0, 1, 2, 3 or 4, and R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0148] In a preferred embodiment of the present invention, the medium further comprises 1% to 10% of one or more compounds of formula VII-1 to VII-9. [ka] In the formula, R 7 w represents a linear alkyl or alkoxy group having 1 to 6 carbon atoms, or a linear alkenyl group having 2 to 6 carbon atoms, where w is an integer from 1 to 6.

[0149] Preferably, the medium of the present invention comprises one or more compounds of formula VIII. [ka] In the formula, R 81 and R 82 These represent, whether identical or different, H, halogen, CN, SCN, a linear alkyl or alkoxy having 1 to 15 carbon atoms, a linear alkenyl or alkenyloxy having 2 to 15 carbon atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 carbon atoms, and one or more CH2 groups of these groups are independent of each other and in a manner in which the oxygen atoms are not directly adjacent to each other. [ka] The atoms may be substituted with -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens.

[0150] A 0 , A 81 , and A 82 Each of these independently represents phenylene-1,4-diyl, where one or two CH groups may be substituted with N, one or more H atoms may be substituted with halogens such as CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2 or OCF3, or cyclohexane-1,4-diyl, where one or two non-adjacent CH2 groups may independently be substituted with O and / or S, and one or more H atoms may be substituted with F, cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl; Z 81 and Z 82 Each of these independently represents -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-, -C2H4-, -C2F4, -CF2CH2-, -CH2CF2-, -CFHCFH-, -CFHCH2-, -CH2CFH-, -CF2CFH-, -CFHCF2-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, or a single bond. n represents 0, 1, 2, or 3, preferably 0, 1, or 2, very preferably 0 or 1, and especially preferably 0. m represents 0, 1, 2, or 3, preferably 0, 1, or 2, very preferably 1 or 2, and especially 1.

[0151] The total concentration of one or more compounds in the medium is in the range of 1% to 20%. A in equation VIII 81 and A82 is preferably phenylene-1,4-diyl which may be monosubstituted or polysubstituted with F, more preferably cyclohexane-1,4-diyl, cyclohexenylene-1,4-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, and very preferably phenylene-1,4-diyl or cyclohexane-1,4-diyl which may be monosubstituted or polysubstituted with F. Z in formula VIII 81 and Z 82 This preferably represents -CF2O-, -OCF2-, or a single bond, very preferably a single bond.

[0152] A in formula VIII 81 and A 82 Particularly preferred [ka] In the formula, L represents a halogen, CF3, or CN, preferably F.

[0153] Furthermore, the compound of formula VIII is preferred, where R 81 and R 82 Each of these independently represents an alkyl, alkoxy, alkenyl, or alkynyl group having H, F, or 1 to 8, preferably 1 to 5, carbon atoms, and each is optionally substituted with a halogen, particularly F.

[0154] R 81 and R 82 Preferably, H represents an optionally fluorinated alkyl or alkoxy having 1 to 7 carbon atoms, an optionally fluorinated alkenyl or alkynyl having 2 to 7 carbon atoms, or an optionally fluorinated cycloalkyl having 3 to 12 carbon atoms.

[0155] Preferably, at least one R 81 and R 82 It is not H, but especially preferably R 81 and R 82 Neither of them is H. 81R is very preferably alkyl. 82 is more preferably H, alkyl, or fluorine. Very preferably, R 81 is alkyl, and R 82 R is either H or alkyl. 81 , R 82 Each of these independently represents an unbranched alkyl group having, very preferably, 1 to 5 carbon atoms. 81 and R 82 If represents a substituted alkyl, alkoxy, alkenyl, or alkynyl, then the two groups R 81 and R 82 The total number of C atoms in is preferably less than 10.

[0156] The preferred compound of formula VIII is selected from the compounds of formula VIIIa. [ka] In the formula, R 1 and R 2 , representing identical or different linear alkyl groups having 1 to 15 carbon atoms, linear alkenyl or branched alkyl groups having 2 to 15 carbon atoms, or alkenyl groups having 3 to 15 carbon atoms, where one or more CH2 groups of these groups are independently of each other. [ka] One or more H atoms may be substituted with fluorine, preferably R 1 and R 2 Both represent a linear alkyl group having 1 to 6 carbon atoms.

[0157] A highly preferred compound of formula VIII is selected from the compounds of formula VIIIa-1 to VIIIa-35. [ka]

[0158] [ka]

[0159] [ka]

[0160] [ka]

[0161] [ka] In the formula, v is an integer between 1 and 6.

[0162] A more preferred compound of formula VIII can be selected from the following sub-formulas. [ka] In the formula, R 81 , R 82 And L have the meanings described above, where L preferably represents F, and r, s and t are independently 0, 1, 2, 3, or 4. r is preferably 1 or 2, very preferably 2, and s and t are independently preferably 0 or 1, very preferably 0. R 81 and R 82 This specifically represents an n-alkyl group having 1 to 5 independent carbon atoms.

[0163] In a first very preferred embodiment, the compound of formula VIII-1 to VIII-6 is selected from the compounds of formula VIII-1a to VIII-6a, and in particular formula VIII-3a: [ka] In the formula, R 81 , R 82 r and s have the meanings defined above.

[0164] In a second, highly preferred embodiment, the compound of formula VIII-1 to VIII-6 is selected from the compounds of formula VIII-1b to VIII-6b, and in particular formula VIII-3b. [ka] In the formula, R 81 , R 82 L, r, and s have the meanings defined above.

[0165] In a third, highly preferred embodiment, the compound of formula VIII-1 to VIII-6 is selected from the compounds of formula VIII-1c to VIII-6c, particularly formula I3-c. [ka] In the formula, R 81 , R 82 L, r, and s have the meanings defined above.

[0166] In a fourth, highly preferred embodiment, the compound of formula VIII-1 to VIII-6 is selected from the compounds of formula VIII-1d to VIII-6d, and in particular formula VIII-3d. [ka] In the formula, R 81 , R 82 L, r, and s have the meanings defined above.

[0167] In a particularly preferred embodiment, the medium of the present invention comprises one or more compounds selected from the group consisting of formulas VIII-1a to VIII-6a, and one or more compounds selected from the group consisting of formulas VIII-1b to VIII-6b.

[0168] Very preferably, the medium comprises one or more compounds selected from the group consisting of compounds of formulas VIII-3a, VIII-3b, VIII-3c, and VIII-3d. [ka] In the formula, R 81 , R 82 L and r have the meanings defined above, and preferably r is 0.

[0169] The most preferred compounds of formula I include, in particular, one or more of the following: [ka] [ka]

[0170] [ka]

[0171] Alternatively or in addition, the following compounds can be used: [ka]

[0172] [ka]

[0173] [ka]

[0174] In a preferred embodiment, the medium comprises one or more compounds of formula IX. [ka] In the formula, R 1 and R 2These groups, whether identical or different, represent H, halogen, a linear alkyl or alkoxy having 1 to 15 carbon atoms, a linear alkenyl or alkenyloxy having 2 to 15 carbon atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy each having 3 to 15 carbon atoms, and one or more CH2 groups of these groups are independent of each other and in a manner in which the oxygen atoms are not directly adjacent to each other. [ka] The atoms may be substituted with -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens.

[0175] L 11 and L 12 Each of these independently represents F, Cl, CF3, or CHF2. L 13 and L 14 Each of these independently represents H, F, Cl, CF3, or CHF2. Y 1 This represents H, F, Cl, CF3, CHF2, or CH3, preferably H or CH3. n is either 0 or 1.

[0176] Preferably, n is 0, Y represents H or CH3, more preferably H, and L 11 and L 12 This is an LC medium containing the compound of formula IX, where F represents F.

[0177] A highly preferred compound of formula IX is selected from the compounds of formulas IX-1 to IX-35. [ka]

[0178] [ka]

[0179] [ka]

[0180] [ka]

[0181] [ka]

[0182] In a preferred embodiment of the present invention, the medium comprises one or more compounds of formula X. [ka] During the ceremony, [ka]

[0183] [ka] R X This represents a linear or branched alkyl or alkoxy group having 1 to 15 carbon atoms, and one or more CH2 groups of these groups are independent of each other and in a manner in which the oxygen atoms are not directly adjacent to each other. [ka] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO- may be substituted, and one or more H atoms may be substituted with a halogen, preferably F.

[0184] X X F, Cl, CN, SF5, SCN, NCS represent halogenated alkyl groups or halogenated alkoxy groups having 1 to 6 carbon atoms each, or halogenated alkenyl groups or halogenated alkenyloxy groups having 2 to 6 carbon atoms each. Z X -C2H4-, -CH2O-, CF2O, -CH=CH-, or a single bond.

[0185] In the compound of formula X, R X This preferably represents an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms, and is preferably linear.

[0186] In the compound of formula X, X Preferably, this is F, Cl, or a monofluorinated or polyfluorinated alkyl or alkoxy group having 1, 2, or 3 carbon atoms, or a monofluorinated or polyfluorinated alkenyl group having 2 or 3 carbon atoms. X The most preferred is F, Cl, CF3, CHF2, OCF3, OCHF2, OCFHCF3, OCFHCHF2, OCFHCHF2, OCF2CH3, OCF2CHF2, OCF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCFHCF2CF3, OCFHCF2CHF2, OCF2CF2CF3, OCF2CF2CClF2, OClFCF2CF3, OCH=CF2 or CH=CF2, very preferably F or OCF3, even more preferably CF3, OCF=CF2, OCHF2 or OCH=CF2, very particularly preferably F, OCF3 or CF3, and most preferably F.

[0187] A preferred compound of formula X is selected from the following sub-formulas. [ka] In the formula, R X X has one of the meanings given by formula X, and preferably represents a linear alkyl having 1 to 6 C atoms, very preferably ethyl, propyl, or butyl, or a linear alkenyl having 2 to 6 C atoms, very preferably vinyl or 1-propenyl, most preferably vinyl, and X X This has one of the meanings given in formula X, and preferably represents F, CF3, or OCF3, very preferably F.

[0188] A highly preferred compound of formula X is selected from the following sub-formulas. [ka]

[0189] [ka]

[0190] [ka]

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] Preferably, the LC medium contains one or more compounds selected from the group consisting of formulas X1-1, X1-3, X2-1, and X2-3. In a preferred embodiment of the present invention, the medium further comprises one or more compounds of formula XI. [ka] In the formula, R XIThis represents H, F, Cl, a linear alkyl or alkoxy having 1 to 15 carbon atoms, a linear alkenyl or alkenyloxy having 2 to 15 carbon atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 carbon atoms, and one or more CH2 groups of these groups are independent of each other and in a manner in which the oxygen atoms are not directly adjacent to each other. [ka] The atoms may be substituted with -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens.

[0195] X XI1 ~X XI4 These are identical or different, representing H or F, preferably at least one X XI1 ~X XI4 represents F, and moreover X XI1 ~X XI4 One of them represents F; Z XI1 and Z XI2 These represent identical or different CH2CH2 or single bonds.

[0196] A preferred compound of formula XI is selected from the compounds of formula XI-1. [ka] In the formula, R XI This represents a linear alkyl group having 1 to 7 carbon atoms, or a linear alkenyl group having 2 to 7 carbon atoms, and one or more CH2 groups of these groups are independently of each other. [ka] X XI4 represents H or F, preferably H.

[0197] Preferably, in addition to or instead of the compound of formula I, the medium contains one or more compounds of formula T. [ka] In the formula, R T1 , and R T2 These groups are identical or distinct and represent H, halogen, CN, SCN, a linear alkyl or alkoxy having 1 to 15 carbon atoms, a linear alkenyl or alkenyloxy having 2 to 15 carbon atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 carbon atoms, and one or more CH2 groups of these groups are independent of each other and in a manner in which the oxygen atoms are not directly adjacent to each other. [ka] The atoms may be substituted with -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O-, or -O-CO-, and one or more H atoms may be substituted with halogens.

[0198] R T3 This represents F, CN, a linear alkyl or alkoxy having 1 to 5 carbon atoms, a linear alkenyl or alkenyloxy having 2 to 5 carbon atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 5 carbon atoms, and the CH2 group in these groups is [ka] It may be substituted with, and one or more H atoms may be substituted with halogens.

[0199] A 0 , A 1 , and A 2Each of these independently represents phenylene-1,4-diyl, where one or two CH groups may be substituted with N, one or more H atoms may be substituted with halogens, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2 or OCF3, cyclohexane-1,4-diyl, one or two non-adjacent CH2 groups may independently be substituted with O and / or S, and one or more H atoms may be substituted with F, cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl; Z 1 and Z 2 Each of these independently represents -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-, -C2H4-, -C2F4, -CF2CH2-, -CH2CF2-, -CFHCFH-, -CFHCH2-, -CH2CFH-, -CF2CFH-, -CFHCF2-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, or a single bond; n represents 0, 1, 2, or 3, preferably 0, 1, or 2, very preferably 0 or 1, and especially preferably 0; m represents 0, 1, 2, or 3, preferably 0, 1, or 2, very preferably 1 or 2, and especially 1.

[0200] A preferred compound of formula T is selected from the following sub-formulas, more preferably from the compounds of formula T-3. [ka]

[0201] In the formula, R T1 , R T2 and R T3The above meaning applies to formula T, where L is a halogen, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2, or OCF3, preferably F, and r, s, and t are independently 0, 1, 2, 3, or 4. r is preferably 1 or 2, very preferably 2, and s and t are independently preferably 0 or 1, very preferably 0. R T1 and R T2 In particular, it represents an alkyl group having 1 to 7 carbon atoms independently or an alkenyl group having 2 to 7 carbon atoms, or R T2 This represents F, CHF2, CF3, OCHF2, or OCF3. R T3 This more preferably represents F or an n-alkyl having 1 to 3 C atoms, very preferably F or CH3, and especially CH3.

[0202] In a fourth, highly preferred embodiment, the compound of formula T-1 to T-6 is selected from the compounds of formula T-1a to T-6a, and in particular is T-3a. [ka] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0203] In a second, highly preferred embodiment, the compound of formula T-1 to T-6 is selected from the compounds of formula T-1b to T-6b, and in particular is the compound of formula T-3b. [ka] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0204] In a third, very preferred embodiment, the compound of formula T-1 to T-6 is selected from the compounds of formula T-1c to T-6c, particularly T-3b. [ka] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0205] In a fourth, highly preferred embodiment, the compound of formula T-1 to T-6 is selected from the compounds of formula T-1d to T-6d, particularly T-3d. [ka] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0206] In a particularly preferred embodiment, the medium of the present invention comprises one or more compounds selected from the group consisting of formulas T-1a to T-6a, and one or more compounds selected from the group consisting of formulas T-1b to T-6b.

[0207] More preferably, the medium comprises one or more compounds selected from the group consisting of formulas T-3a, T-3c, and T-3d. [ka] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0208] Alternatively, an LC medium containing a compound of the following formula T is particularly preferred. [ka]

[0209] [ka] In the formula, n is 1, 2, 3, 4, 5, 6, or 7.

[0210] Alternatively or in addition, the following compound of formula T can be used: [ka]

[0211] [ka] [ka]

[0212] In another preferred embodiment, the compound of formula T is selected from the following sub-formulas. [ka] [ka] In the formula, R T1 The terms have the meaning defined above for equation T and its sub-equations.

[0213] Further preferred embodiments are listed below. a) A liquid crystal medium comprising at least one compound of formulas Z-1 to Z-8, preferably formulas Z-2, Z-4, and Z-6, and very preferably formula Z-4. [ka] In the formula, R Z The above R 2AThis means that (O) represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms, (O) represents oxygen or a single bond, and alkyl represents an alkyl group having 1 to 7 carbon atoms.

[0214] b) A preferred liquid crystal medium according to the present invention comprises one or more substances containing tetrahydronaphthyl or naphthyl units, for example, compounds of formula N1 to N5. [ka] In the formula, R 1N and R 2N Each of these is independent of the others, as described above R 2A It has the meaning of, and preferably represents a linear alkyl, linear alkoxy, or linear alkenyl, Z 1 and Z 2 Each of these independently represents -C2H4-, -CH=CH-, -(CH2)4-, -(CH2)3O-, -O(CH2)3-, -CH=CHCH2CH2-, -CH2CH2CH=CH-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2O-, -OCF2-, -CH2-, or a single bond.

[0215] c) A preferred mixture comprises one or more compounds selected from the group consisting of difluorodibenzochromane compounds of formulas BC, CR, PH-1 and PH-2. [ka] In the formula, R B1 , R B2 , R CR1 , R CR2 , R P1 , R P2 Each of these is independent of the other, and R in Equation III 31 It has the meaning of and c is 0, 1, or 2. 1 and R 2 Preferably, each element independently represents an alkyl or alkoxy having 1 to 6 carbon atoms.

[0216] The medium preferably contains one or more compounds of formulas BC, CR, and PH-1 and PH-2 in a total concentration ranging from 0.5% to 15%.

[0217] Particularly preferred compounds of formulas BC, CR, and PH-1 are compounds BC-1 to BC-7, CR-1 to CR-5, and BP-1 to BP-7. [ka] [ka]

[0218] [ka]

[0219] In the formula, alkyl and alkyl* each independently represent a linear alkyl group having 1 to 6 carbon atoms. alkenyl and alkenyl* each represent a linear alkenyl group having 2 to 6 carbon atoms, independently of each other.

[0220] More preferably are mixtures containing one, two, or three compounds of formula BC-2, BC-3, BP-2, and / or BP-3, and very preferably BP-2 and / or BP-3, particularly BP-3.

[0221] d) A preferred mixture contains one or more indane compounds of formula In. [ka] In In the formula, R 11 , R 12 , and R 13Each of these independently represents a linear alkyl, alkoxy, alkoxyalkyl, or alkenyl group having 1 to 6 carbon atoms. Or R 12 and R 13 This represents a halogen, preferably F.

[0222] [ka] i represents 0, 1, or 2.

[0223] Preferred compounds of formula In are the compounds of formulas In-1 to In-16 shown below. [ka]

[0224] [ka]

[0225] Of particular preference are compounds of formulas In-1, In-2, In-3, and In-4.

[0226] e) A preferred mixture further comprises one or more compounds of formulas L-1 to L-11. [ka]

[0227] In the formula, R, R 1 and R 2 Each of these independently of the other is R in equation IIA above. 2A The meanings shown are as follows: alkyl represents an alkyl group having 1 to 6 carbon atoms, and the parameter s represents 1 or 2. The compounds of formulas L-1 to L-9 are preferably used at a concentration of 5 to 15% by weight, particularly 5 to 12% by weight, and very preferably 8 to 10% by weight.

[0228] f) A preferred mixture further comprises one or more compounds of formula IIA-Y. [ka] In the formula, R 11 and R 12 This is R in equation IIA above. 2A Having any of the meanings shown, L 1 and L 2 These are the same or different elements, representing F or Cl. Compounds of formula IIA-Y are preferably used at a concentration of 0.5 to 5% by weight.

[0229] The preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas. [ka] [ka]

[0230] In the formula, Alkyl and Alkyl* each independently represent a linear alkyl group having 1 to 6 carbon atoms, Alkoxy represents a linear alkoxy group having 1 to 6 carbon atoms, Alkenyl and Alkenyl* each independently represent a linear alkenyl group having 2 to 6 carbon atoms, and O represents an oxygen atom or a single bond. Alkenyl and Alkenyl* preferably represent CH2=CH-, CH2=CHCH2CH2-, CH3-CH=CH-, CH3-CH2-CH=CH-, CH3-(CH2)2-CH=CH-, CH3-(CH2)3-CH=CH- or CH3-CH=CH-(CH2)2-, L 1 and L 2 Each of these independently represents F, Cl, CH3, CF3, or CHF2, preferably Cl or F, and very preferably F.

[0231] Particularly preferred compounds of formula IIA-Y are selected from the group consisting of the following sub-formulas. [ka] In the formula, Alkoxy and alkoxy* have the meanings defined above, and preferably represent methoxy, ethoxy, n-propyloxy, n-butyloxy, or n-pentyloxy.

[0232] Preferably, the medium of the present invention comprises a compound selected from the group consisting of compounds of formulas ST-1 to ST-19, and very preferably compounds of formula ST-3. [ka]

[0233] [ka] [ka]

[0234] [ka] [ka] In the formula, R ST This represents an alkyl or alkoxy group having H and 1 to 15 C atoms, and furthermore, one or more CH2 groups in these groups are independent of each other and in a manner in which the O atoms are not directly adjacent to each other, such as -C≡C-, -CF2O-, -OCF2-, -CH=CH-, [ka] Substitutions may be made with -O-, -CO-O-, and -O-CO-, respectively, and one or more H atoms may be substituted with halogens. [ka] Z ST These each independently represent -CO-O-, -O-CO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CH2-, -CH2CH2-, -(CH2)4-, -CH=CH-, -CH2O-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C-, or a single bond. p represents 0, 1, or 2. q represents 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0235] Among the compounds of formula ST, the compounds of the following formula are given particular preference. [ka]

[0236] [ka] [ka]

[0237] In the compounds of formulas ST-3a and ST-3b, n preferably represents 3. In the compound of formula ST-2a, n preferably represents 7.

[0238] A particularly preferred mixture of the present invention comprises one or more stabilizers selected from the group of compounds of formula ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1, and ST-12. [ka] [ka]

[0239] Preferably, the medium contains one or more compounds of formula S. [ka] In the formula, Ar represents a methylene group or aromatic hydrocarbon group having 6 to 40 carbon atoms, or a heteroaromatic hydrocarbon group having 4 to 40 carbon atoms; preferably, it represents an aromatic hydrocarbon group having 6 to 40 carbon atoms; Sp represents a spacer group; R S represents H, an alkyl group having 1 to 12 C atoms, or an alkenyl group having 2 to 12 C atoms; Z S -O-, -C(O)O-, -(CH2) z -or-(CH2) z O- represents a single bond, HA is [ka] R H H, O · , CH3, OH or OR S It represents; R S1 , R S2 , R S3 and R S4 This represents an alkyl group that is identical or different and has 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, and is very preferably CH3; G is H or R S or base Z S - Represents HA, z is an integer from 1 to 6. q is 2, 3, or 4, preferably 3 or 4.

[0240] In formula S, aryl represents an aromatic or heteroaromatic hydrocarbon group having 4 to 40 carbon atoms, comprising 1, 2, 3, or 4 aromatic rings (including fused rings which may be linked directly or via alkylene linking groups having 1 to 12 carbon atoms), one or more H atoms optionally substituted with alkyl or alkoxy groups having 1 to 6 carbon atoms, or alkenyl groups having 2 to 6 carbon atoms, or CN, CF3, or halogens, and one or more CH2 groups may be independently substituted with -O-, -S-, -NH-, -N(C1-C4-alkyl)-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, or -C≡C- such that the O or S atoms are not directly linked to each other.

[0241] Preferred aryl groups are benzene, naphthalene, anthracene, biphenyl, m-terphenyl, p-terphenyl, and (phenylalkyl)benzene, where alkyl is a linear alkyl having 1 to 12 carbon atoms.

[0242] In a preferred embodiment, the medium of the present invention comprises a compound of formula S, where parameter q is 3 and G is the group Z S - Represents HA

[0243] In another preferred embodiment, the medium of the present invention comprises a compound of formula S, where the parameter q is 4 and G is H or R S It represents.

[0244] The compound of formula S is preferably selected from the compounds of formulas S-1, S-2, and S-3. [ka] In the formula, R H It has the meaning described above, preferably H or O . This represents, Each instance of Sp represents a spacer group, whether identical or different. W represents a linear or branched alkylene having 1 to 12 optionally unsaturated carbon atoms, where one or more non-adjacent -CH2- groups may be substituted with -O-.

[0245] The preferred compound of formula S-1 is selected from the compounds of formula S-1-1. [ka] In the formula, R H It has the meaning described above, preferably H or O . This represents a value where n is an integer from 0 to 12, preferably 5, 6, 7, 8, or 9, and very preferably 7.

[0246] The preferred compound of formula S-2 is selected from the compounds of formula S-2-1. [ka] In the formula, R H It has the meaning described above, preferably H or O . Represents n2, where n2 is the same or different each time it appears, preferably an integer from 1 to 12, preferably 2, 3, 4, 5, or 6, very preferably 3, and R S Each occurrence may be the same or different, and preferably similarly, it represents an alkyl group having 1 to 6 C atoms, preferably n-butyl.

[0247] The preferred compound of formula S-3 is selected from the compounds of formula S-3-1. [ka] In the formula, R H It has the meaning described above, preferably H or O . This represents a value where n is an integer between 0 and 12, preferably 5, 6, 7, 8, or 9, and very preferably 7.

[0248] Compounds of formula S and ST-1 to ST-18 are preferably present in the liquid crystal mixture of the present invention in an amount of 0.005 to 0.5% based on the mixture.

[0249] If the mixture according to the present invention contains two or more compounds from the group of compounds of formula S and ST-1 to ST-18, the concentration increases accordingly, to 0.01 to 1% relative to the mixture in the case of two compounds.

[0250] However, the total proportion of compounds of formula S and ST-1 to ST-18 based on the mixture according to the present invention should not exceed 2%.

[0251] The liquid crystal medium according to the present invention, also referred to herein as a liquid crystal host mixture, is suitable for use in polymer-stabilized displays. For this purpose, the medium according to the present invention optionally comprises one or more polymerizable compounds of formula P. P-Sp-A 1 -(Z 1 -A 2 ) z -RP In the formula, each element is independent of the others, and each instance is either identical or different. P represents a polymerizable group, Sp represents a spacer group or a single bond. A 1 , A 2 represents an aromatic, heteroaromatic, alicyclic, or heterocyclic group, preferably having 4 to 25 ring atoms, and the group may also include fused rings, and the group is unsubstituted, monosubstituted, or polysubstituted with L. Z 1 -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2-, -(CF2) n1 -, -CH=CH-, -CF=CF-, -CH=CF-, -CF=CH-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, -CH2-CH2-CO-O-, -O-CO-CH2-CH2-, -CR 0 R 00 - or represents a single bond, R0 , R 00 This represents an alkyl group having H or 1 to 12 C atoms. R represents H, L, or P-Sp-, L represents a linear, branched, or cyclic alkyl group having F, Cl, -CN, P-Sp-, or 1 to 25 C atoms, where one or more non-adjacent CH2 groups are optionally substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, where O and / or S atoms are not directly linked to each other independently, and where one or more H atoms are optionally substituted with P-Sp-, F, or Cl. z is 0, 1, 2, or 3. n1 is 1, 2, 3, or 4.

[0252] As used herein, the term “reliability” refers to the quality of a display’s performance over time, under various stress loads such as light load, temperature, humidity, and voltage, and display effects known to those skilled in the art in the field of liquid crystal displays, such as image fixation (area and line image fixation), unevenness, and blemishes. A standard parameter used to classify reliability is typically the voltage retention rate (VHR), which is a measure of the ability of a test display to maintain a constant electrical voltage. A high VHR is a prerequisite for high reliability of the LC medium.

[0253] Unless otherwise specified, the term "PSA" is used to refer to polymer-maintained orientation displays in general, and the term "PS" is used to refer to specific display modes such as PS-VA and PS-TN.

[0254] As used herein, the terms “active layer” and “switchable layer” mean layers in an electro-optical display, such as an LC display, that contain one or more molecules having structural and optical anisotropy, such as LC molecules, whose orientation changes in response to external stimuli, such as an electric or magnetic field, resulting in a change in the transparency of the layer to polarized or unpolarized light.

[0255] As used herein, the terms “tilt” and “tilt angle” are understood to mean the tilted orientation of LC molecules in an LC medium relative to the cell surface in an LC display (preferably a PSA display). In this specification, the tilt angle means the average angle (less than 90°) between the molecular long axis (LC director) of the LC molecule and the surface of the flat, parallel outer plate forming the LC cell. In this specification, a low tilt angle (i.e., far from 90°) corresponds to a large tilt. Appropriate methods for measuring the tilt angle are given in the examples. Unless otherwise indicated, the tilt angle values ​​disclosed above and below refer to this measurement method.

[0256] As used herein, the terms “reactive mesogen” and “RM” are understood to mean a compound containing a mesogen or liquid crystal skeleton and one or more functional groups linked to that skeleton and suitable for polymerization, and the functional group is also referred to as a “polymerizable group” or “P”.

[0257] Unless otherwise stated herein, the term "polymerizable compound" is understood to mean a polymerizable monomer compound.

[0258] As used herein, the term “low molecular weight compound” is understood to mean a monomer and / or a compound not prepared by polymerization, as opposed to “polymer compound” or “polymer.”

[0259] As used herein, the term “non-polymerizable compound” is understood to mean a compound that does not contain functional groups suitable for polymerization under the conditions typically applied for the polymerization of RM.

[0260] As used herein, the term “mesogenic group” refers to a group known to those skilled in the art and documented in the literature, which, due to the anisotropy of its attractive and repulsive interactions, essentially contributes to the generation of a liquid crystal (LC) phase in low-molecular-weight or high-molecular-weight materials. Compounds containing a mesogenic group (mesogenic compounds) do not necessarily have an LC phase themselves. It is also possible for a mesogenic compound to exhibit LC phase behavior only after mixing with other compounds and / or polymerization. Typical mesogenic groups are, for example, rigid rod-shaped or disc-shaped units. An overview of the terms and definitions used with respect to mesogens or LC compounds is given in Pure Appl. Chem. 2001, Vol. 73 (No. 5), p. 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340–6368.

[0261] As used herein, the terms “optically active” and “chiral” are synonyms for materials that can induce a helical pitch in a nematic host material, and are also called “chiral dopants.”

[0262] As used herein, the term “spacer group” is also hereafter referred to as “Sp,” and is known to those skilled in the art and described in the literature, see, for example, Pure Appl. Chem. 2001, Vol. 73 (No. 5), p. 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, Vol. 116, pp. 6340–6368. As used herein, the term “spacer group” or “spacer” means a flexible group, such as an alkylene group, that links a mesogenic group and a polymerizable group in a polymerizable mesogenic compound.

[0263] Similarly, in the compound of formula I, the spacer group is linked to the optically active central hydrocarbon group, stabilizing the hindered amine functional group.

[0264] Above and below, [ka] This represents a trans-1,4-cyclohexylene ring.

[0265] basis [ka] In this case, the single bond between the two ring atoms can be linked to any unbonded position on the benzene ring.

[0266] In the above and below, "organic group" refers to a carbon or hydrocarbon group.

[0267] The term "carbon group" refers to a monovalent or polyvalent organic group containing at least one carbon atom, which may either contain no further atoms (e.g., -C≡C-) or may contain one or more further atoms such as N, O, S, B, P, Si, Se, As, Te, or Ge (e.g., carbonyl). The term "hydrocarbon group" refers to a carbon group that additionally contains one or more H atoms and may contain one or more heteroatoms such as N, O, S, B, P, Si, Se, As, Te, or Ge.

[0268] "Halogen" represents F, Cl, Br, or I, preferably F or Cl.

[0269] -CO-, -C(=O)-, and -C(O)- are carbonyl groups, i.e., [ka]

[0270] The carbon or hydrocarbon group may be saturated or unsaturated. Unsaturated groups include, for example, aryl, alkenyl, or alkynyl groups. The carbon or hydrocarbon group having more than three C atoms may be linear, branched, and / or cyclic, and may also contain spirolinking or fused rings.

[0271] The terms "alkyl," "aryl," and "heteroaryl" also include polyvalent groups, such as alkylenes, arylenes, and heteroarylenes.

[0272] The term "aryl" refers to an aromatic carbon group or a group derived therefrom. The term "heteroaryl" refers to an "aryl" as defined above, preferably containing one or more heteroatoms selected from N, O, S, Se, Te, Si, and Ge.

[0273] Preferred carbon and hydrocarbon groups are linear, branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy groups having 1 to 40, preferably 1 to 20, and very preferably 1 to 12 C atoms, optionally substituted aryl or aryloxy groups having 5 to 30, preferably 6 to 25 C atoms, or optionally substituted alkylaryl, arylalkyl, alkylaryloxy, arylalkyloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy groups having 5 to 30, preferably 6 to 25 C atoms, wherein one or more C atoms may preferably be substituted with heteroatoms selected from N, O, S, Se, Te, Si and Ge.

[0274] A more preferred carbon and hydrocarbon group is C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkinyl, C3-C 20 Allyl, C4-C 20 Alkyldienyl, C4-C 20 Polyenyl, C6-C 20 Cycloalkyl, C4-C 15 Cycloalkenyl, C6-C 30 Ariel, C6-C 30 Alkylaryl, C6-C 30 Arylalkyl, C6-C 30 Alkylaryloxy, C6-C30 Arylalkyloxy, C2-C 30 Heteroaryl, C2-C 30 It is a heteroaryloxy.

[0275] C1-C 12 Alkyl, C2-C 12 Alkenyl, C2-C 12 Alkinyl, C6-C 25 Aryl and C2-C 25 Heteroaryls are particularly preferred.

[0276] A more preferred carbon and hydrocarbon group is a linear, branched, or cyclic alkyl having 1 to 20, preferably 1 to 12 C atoms, the group being unsubstituted or monosubstituted or polysubstituted with F, Cl, Br, I, or CN, and one or more non-adjacent CH2 groups independently of each other such that the O and / or S atoms are not directly bonded to each other, -C(R x )=C(R x )-, -C≡-, -N(R x Substitutions may be made with -, -O-, -S-, -CO-, -CO-O-, -O-CO-, and -O-CO-O- respectively.

[0277] R x Preferably, represents a linear, branched, or cyclic alkyl chain having H, F, Cl, CN, or 1 to 25 carbon atoms (furthermore, one or more non-adjacent carbon atoms may be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, and one or more H atoms may be substituted with F or Cl), or an optionally substituted aryl or aryloxy group having 6 to 30 carbon atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 30 carbon atoms.

[0278] Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, dodecanyl, trifluoromethyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, and perfluorohexyl.

[0279] Preferred alkenyl groups include, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, and cyclooctenyl.

[0280] Preferred alkynyl groups include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, and octinyl.

[0281] Preferred alkoxy groups include, for example, methoxy, ethoxy, 2-methoxyethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2-methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, and n-dodecoxy.

[0282] Preferred amino groups include, for example, dimethylamino, methylamino, methylphenylamino, and phenylamino.

[0283] The aryl and heteroaryl groups may be monocyclic or polycyclic; that is, they may contain one ring (e.g., phenyl) or two or more rings, and the group may be condensed (e.g., naphthyl) or covalently linked (e.g., biphenyl), or may contain a combination of condensed and linked rings. The heteroaryl group preferably contains one or more heteroatoms selected from O, N, S, and Se.

[0284] Monocyclic, bicyclic, or tricyclic aryl groups having 6 to 25 carbon atoms and monocyclic, bicyclic, or tricyclic heteroaryl groups having 5 to 25 ring atoms are particularly preferred, and these groups may contain fused rings or be substituted. Furthermore, 5-membered, 6-membered, or 7-membered aryl and heteroaryl groups are preferred, however, one or more CH groups may be substituted with N, S, or O such that the O atoms and / or S atoms are not directly linked to each other.

[0285] Preferred aryl groups include, for example, phenyl, biphenyl, terphenyl, [1,1':3',1'']terphenyl-2'-yl, naphthyl, anthracene, binaphthyl, phenanthrene, 9,10-dihydrophenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene, indenofluorene, spirobifluorene, and the like.

[0286] Preferred heteroaryl groups include, for example, five-membered rings (e.g., pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, furan, thiophene, selenofen, oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2 ,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole), 6-membered rings (e.g., pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine), or condensation groups (e.g., indole, isoindole, indidine, indazole, benzimidazole, benzotriazole) Purine, naphthimidazole, phenanthimidazole, pyridoimidazole, pyrazineimidazole, quinoxalineimidazole, benzoxazole, naphthoxazole, anthroxazole, phenantroxazole, isoxazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, quinoline, isoquinoline, pteridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, benzo Soquinoline, acridine, phenothiazine, phenoxazine, benzopyridazine, benzopyrimidine, quinoxaline, phenazine, naphthyridine, azacarbazole, benzocarbolin, phenantholidine, phenanthroline, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithienothiophene, isobenzothiophene, dibenzothiophene, benzothiophene, benzothiadiazothiophene), or combinations of these groups.

[0287] The aryl and heteroaryl groups described above and below may be substituted with alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl, or further aryl or heteroaryl groups.

[0288] (Non-aromatic) alicyclic and heterocyclic groups include both saturated rings, i.e., those containing exclusively single bonds, and partially unsaturated rings, i.e., those that may also contain multiple bonds. Heterocyclic rings preferably contain one or more heteroatoms selected from Si, O, N, S, and Se.

[0289] (Non-aromatic) alicyclic and heterocyclic groups may be monocyclic, i.e., containing only one ring (e.g., cyclohexane), or polycyclic, i.e., containing multiple rings (e.g., decahydronaphthalene or bicyclooctane). Saturated groups are particularly preferred. Furthermore, monocyclic, bicyclic, or tricyclic groups having 5 to 25 ring atoms are preferred, and these groups may contain fused rings and may be substituted. Furthermore, 5-membered, 6-membered, 7-membered, or 8-membered carbocyclic groups are preferred, provided that one or more C atoms are substituted with Si, and / or one or more CH groups are substituted with N, and / or one or more non-adjacent CH2 groups are substituted with -O- and / or -S-.

[0290] Preferred alicyclic and heterocyclic groups include, for example, five-membered groups such as cyclopentane, tetrahydrofuran, tetrahydrothiofuran, and pyrrolidine; six-membered groups such as cyclohexane, silinane, cyclohexene, tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, 1,3-dithiane, and piperidine; seven-membered groups such as cycloheptane; and condensation groups such as tetrahydronaphthalene, decahydronaphthalene, indane, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, and octahydro-4,7-methanoindan-2,5-diyl.

[0291] Preferred substituents include, for example, dissolution-promoting groups such as alkyl or alkoxy groups, electron-withdrawing groups such as fluorine, nitro or nitrile groups, or substituents that increase the glass transition temperature (Tg) in the polymer, particularly bulky groups such as t-butyl or optionally substituted aryl groups.

[0292] Preferred substituents are referred to as "L" below. S It is also called, for example, F, Cl, Br, I, -CN, -NO2, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R x )2, -C(=O)Y 1 -C(=O)R x , -N(R x )2. A linear or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms each (wherein one or more H atoms are optionally substituted with F or Cl), an optionally substituted silyl having 1 to 20 Si atoms, or an optionally substituted aryl having 6 to 25, preferably 6 to 15 C atoms.

[0293] In the formula, R x represents a linear, branched, or cyclic alkyl group having H, F, Cl, CN, or 1 to 25 C atoms, where one or more non-adjacent CH2 groups are optionally substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- so that the O- and / S- atoms are not directly linked to each other, and one or more H atoms are optionally substituted with F, Cl, P- or P-Sp-, respectively, Y 1 This represents halogen.

[0294] "Substituted silyl or aryl" is preferably a halogen, -CN, R 0 , -OR 0 ,-CO-R 0 , -CO-OR 0 ,-O-CO-R 0 or -O-CO-OR 0 This means substitution by R, however, 0 This represents an alkyl group having H or 1 to 20 C atoms.

[0295] Particularly preferred substituents L include, for example, F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5, and phenyl. A 1 and A 2 is very preferable [ka] This represents, in the formula, L has one of the meanings shown above, and r represents 0, 1, 2, 3 or 4, in particular [ka]

[0296] The polymerizable group P is suitable for polymerization reactions such as free radical or ionic chain polymerization, polyaddition or polycondensation, or for polymer-like reactions such as addition or condensation onto a polymer backbone. Groups for chain polymerization, particularly those containing a C=C double bond or a C≡C triple bond, and groups suitable for ring-opening polymerization, such as oxetane or epoxide groups, are especially preferred.

[0297] The preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] 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 2W 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 Selected from the group consisting of Si-, in the formula, W 1 This represents H, F, Cl, CN, CF3, phenyl, or alkyl having 1 to 5 C atoms, especially H, F, Cl or CH3, and W 2 and W 3 Each of these independently represents an alkyl group having H or 1 to 5 C atoms, particularly H, methyl, ethyl, or n-propyl, and W 4 , W 5 and W 6 Each of these independently represents Cl, an oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 k1, k2, and k3 each independently represent an alkyl group having H, Cl, or 1 to 5 C atoms, Phe represents a 1,4-phenylene which may be substituted with one or more groups L as defined above, other than PSp-, k1, k2, and k3 each independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0298] A very preferred group P is CH2=CW 1 -CO-O-, CH2=CW 1 -CO-, [ka] CH2=CW 2 -O-, CH2=CW 2 -, CW 1 =CH-CO-(O) k3 -, CW 1=CH-CO-NH-, CH2=CW 1 -CO-NH-, (CH2=CH)2CH-OCO-, (CH2=CH-CH2)2CH-OCO-, (CH2=CH)2CH-O-, (CH2=CH-CH2)2N-, (CH2=CH-CH2)2N-CO-, CH2=CW 1 -CO-NH-, CH2=CH-(COO) k1 -Phe-(O) k2 -, CH2=CH-(CO) k1 -Phe-(O) k2 -, Phe-CH=CH- and W 4 W 5 W 6 Selected from the group consisting of Si-, in the formula, W 1 is represented by H, F, Cl, CN, CF3, phenyl, or alkyl having 1 to 5 C atoms, especially H, F, Cl or CH3, and W 2 and W 3 Each of these independently represents an alkyl group having H or 1 to 5 C atoms, particularly H, methyl, ethyl, or n-propyl, and W 4 , W 5 and W 6 Each of these independently represents Cl, an oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, and W 7 and W 8 Each of the following independently represents H, Cl, or an alkyl group having 1 to 5 C atoms; Phe represents 1,4-phenylene; k1, k2, and k3 independently represent 0 or 1, k3 preferably represents 1, and k4 represents an integer from 1 to 10.

[0299] A particularly preferred group P is CH2=CW 1 -CO-O-, especially CH2=CH-CO-O-, CH2=C(CH3)-CO-O- and CH2=CF-CO-O-, and furthermore CH2=CH-O-, (CH2=CH)2CH-O-CO-, (CH2=CH)2CH-O-, [ka]

[0300] A more preferred polymerizable group P is selected from the group consisting of vinyl oxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide, and most preferably selected from the group consisting of acrylate and methacrylate.

[0301] When the spacer group Sp is different from the single bond, Sp is preferably of the formula Sp"-X", where Sp" and X" have the following meanings, such that each group P-Sp- corresponds to the formula R-Sp"-X"-.

[0302] Sp" represents a linear or branched alkylene having 1 to 20, preferably 1 to 12, carbon atoms, the group being optionally monosubstituted or polysubstituted with F, Cl, Br, I, or CN, and furthermore, one or more non-adjacent CH2 groups are independently of each other such that the O and / or S atoms are not directly linked to each other, such as -O-, -S-, -NH-, -N(R 0 )-,-Si(R 0 R 00 )-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 )-CO-O-,-O-CO-N(R 0 )-,-N(R 0 )-CO-N(R 00 )-, -CH=CH- or -C≡C- can be substituted respectively. X" is -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-,-N(R 0 )-CO-, -N(R 0 )-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 2 =CY 3-, -C≡C-, -CH=CH-CO-O-, -O-CO-CH=CH-, or single bond are represented. R 0 and R 00 Each of these independently represents an alkyl group having H or 1 to 20 C atoms. Y 2 and Y 3 Each of these elements independently represents either H, F, Cl, or CN. X is sometimes -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 -CO-, -NR 0 -CO-NR 00 - Or it represents a single conjunction.

[0303] Typical spacer bases Sp and -Sp"-X"- are, for example, -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO-O-, -(CH2CH2O) q1 -CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR 0 R 00 -O) p1 - and in the formula, p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, R 0 and R 00 The above has the meanings shown.

[0304] Particularly preferred groups are Sp and -Sp"-X"-, which are -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -O-CO-, -(CH2) p1 -CO-O-, -(CH2) p1 The expression is -O-CO-O-, and p1 and q1 have the meanings shown above.

[0305] Particularly preferred groups Sp'' in their linear forms are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1-methylalkylene, etenylene, propenylene, and butenylene.

[0306] In preferred embodiments of the present invention, compounds of formula P and its subformulas are such that the group Sp-P is Sp(P) s The material contains a spacer group Sp (branched polymerizable group) substituted with one or more polymerizable groups P, corresponding to (wherein s≧2).

[0307] A preferred compound of formula P according to this preferred embodiment is one in which s is 2, i.e., a compound containing the group Sp(P)2. A very preferred compound of formula P according to this preferred embodiment contains a group selected from the following formulas. [ka]

[0308] In the formula, P is defined as in formula P, Alkyl groups represent linear or branched alkylenes having single bonds or 1 to 12 carbon atoms, and the group is either unsubstituted or monosubstituted or polysubstituted with F, Cl, or CN, and one or more non-adjacent CH2 groups are each independently of each other such that the O and / or S atoms are not directly bonded to each other, -C(R 0 )=C(R 0 )-, -C≡C-, -N(R 0 )-, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- can be substituted, R 0 It has the above meaning, aa and bb each independently represent 0, 1, 2, 3, 4, 5, or 6. X has one of the meanings shown in "X", and is preferably O, CO, SO2, O-CO-, CO-O, or a single bond.

[0309] A preferred spacer base Sp(P)2 is selected from formulas S1, S2, and S3.

[0310] A highly preferred spacer base Sp(P)2 is selected from the following sub-formulas. [ka]

[0311] As described above and below, in compounds of formula P and its subformulas, P is preferably selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane, and epoxide, and most preferably selected from the group consisting of acrylate and methacrylate.

[0312] All polymerizable groups P present in the compound have the same meaning and very preferably represent acrylate or methacrylate, most preferably methacrylate. Compounds of formula P and its subformulas as described above and below are even more preferred.

[0313] In the compounds of formula P and its sub-formulas as described above and below, R preferably represents P-Sp-.

[0314] Sp is a single bond or -(CH2) p1 -, -O-(CH2) p1 -, -O-CO-(CH2) p1 , or -CO-O-(CH2) p1 This represents a compound where p1 is 2, 3, 4, 5, or 6, and Sp is -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 In this case, compounds of formula P and its sub-formulas as described above and below, in which the O atom or CO group is linked to a benzene ring, are even more preferred.

[0315] Compounds of formula P and its subformulas as described above and below, in which at least one group Sp is a single bond, are even more preferred.

[0316] At least one group Sp differs from a single bond, preferably -(CH2) p1 -, -O-(CH2) p1 -, -O-CO-(CH2) p1 , or -CO-O-(CH2) p1 Selected from, where p1 is 2, 3, 4, 5 or 6, and Sp is -O-(CH2) p1 -, -O-CO-(CH2) p1 or -CO-O-(CH2) p1 In this case, compounds of formula P and its sub-formulas as described above and below, in which the O atom or CO group is linked to a benzene ring, are even more preferred.

[0317] A highly preferred group in formula P -A 1 -(ZA 2 ) z - is selected from the following formula. [ka] In the formula, at least one benzene ring is substituted with at least one group L, and the benzene ring is optionally further substituted with one or more groups L or P-Sp-.

[0318] Preferred compounds of formula P and its subformulas are selected from the following preferred embodiments (including any combination thereof). • All groups P in a compound have the same meaning. ·-A 1 -(ZA 2 ) z - is selected from A1, A2, and A5. The compound has exactly two polymerizable groups (represented by group P). The compound has exactly three polymerizable groups (represented by group P). P is selected from the group consisting of acrylate, methacrylate, and oxetane, and is very preferably acrylate or methacrylate. P is methacrylate. • All Sp groups are single bonds. • At least one of the Sp groups is a single bond, and at least one of the Sp groups is not a single bond. • If Sp is different from a single bond, -(CH2) p2 -,-(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 The formula is -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O atom or CO group is each linked to a benzene ring. • Sp is a single bond, or -(CH2) p2 -,-(CH2) p2 -O-, -(CH2) p2 -CO-O-, -(CH2) p2 The formula represents -O-CO-, where p2 is 2, 3, 4, 5, or 6, and the O atom or CO group is linked to a benzene ring. ·R represents P-Sp- • R does not represent or does not contain a polymerizable group. • R does not represent or does not contain a polymerizable group, and represents an alkyl group having 1 to 25 C atoms in a linear, branched, or cyclic structure, wherein one or more non-adjacent CH2 groups may be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- such that the O and / or S atoms are not directly linked to each other, wherein one or more H atoms are each F, Cl, or L a It can be replaced with this. L or L' represents F, Cl, or CN. L is F.

[0319] A suitable and preferred compound for formula P is selected from the following formulas. [ka]

[0320] [ka]

[0321] [ka] [ka] [ka]

[0322] In the formula, each unit has the following meaning: P 1 , P 2 and P 3 Each of these independently represents an acrylate or methacrylate group. Sp 1 , Sp 2 and Sp 3 Each of these independently represents a spacer group having one of the above and below meanings for a single bond or Sp, and is particularly preferably -(CH2) p1 -,-(CH2) p1 -O-, -(CH2) p1 -CO-O-, -(CH2) p1 -O-CO- or -(CH2) p1 -O-CO-O- represents -O-CO-O-, where p1 is an integer from 1 to 12, and there exists a basis P 1 -Sp 1 -, P 2 -Sp 2 -and P 3 -Sp 3 - At least one of R aa One or more base P, provided that they are different from 1 -Sp 1 -, P 2 -Sp 2 -and P 3 -Sp 3 - is Raa This can be expressed as, R aa represents a linear or branched alkyl group having H, F, Cl, CN, or 1 to 25 C atoms, provided that in addition, one or more non-adjacent CH2 groups are included such that, in each case, the O and / or S atoms are not directly linked to each other, with -C(R 0 )=C(R 00 )-, -C≡C-, -N(R 0 Substitutions may include -, -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, and in addition, one or more H atoms may be replaced with F, Cl, CN or P. 1 -Sp 1 It may be substituted with - and particularly preferably represents a linear or branched, optionally monofluorinated or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy group having 1 to 12 C atoms (wherein alkenyl and alkynyl groups have at least 2 C atoms, and branched groups have at least 3 C atoms), R 0 , R 00 Each of these independently represents an alkyl group having H or 1 to 12 C atoms, appearing identically or differently each time. R y and R z Each of these independently represents H, F, CH3, or CF3. X 1 , X 2 and X 3 Each of these independently represents a -CO-O-, -O-CO-, or single bond. Z 1 -O-, -CO-, -C(R y R z )- or -CF2CF2- represents, Z 2 and Z 3 These are, independently of each other, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, or -(CH2) n- This represents n being 2, 3, or 4. Each instance of L represents, whether identical or different, an alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, either mono- or polyfluorinated, F, Cl, CN, or linear or branched, preferably F. L' and L'' each represent H, F, or Cl independently of each other. k represents 0 or 1, r represents 0, 1, 2, 3, or 4. s represents 0, 1, 2, or 3. t represents 0, 1, or 2. x represents either 0 or 1.

[0323] Of particular preference are compounds of formulas P2, P13, P17, P22, P23, P24, P30, P31, and P32.

[0324] Even more preferred are the trireactive compounds P15-P30, particularly P17, P18, P19, P22, P23, P24, P25, P26, P30, P31, and P32.

[0325] In the compounds of formulas P1 to P32, [ka]

[0326] In the formula, L, each time it appears, is the same or different and has one of the meanings shown above and below, preferably F, Cl, CN, NO2, CH3, C2H5, C(CH3)3, CH(CH3)2, CH2CH(CH3)C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF3, OCF3, OCHF2, OC2F5 or P-Sp-, very preferably F, Cl, CN, CH3, C2H5, OCH3, COCH3, OCF3 or P-Sp-, more preferably F, Cl, CH3, OCH3, COCH3 or OCF3, particularly F or CH3.

[0327] A particularly preferred compound of formula P is selected from Table E below.

[0328] To manufacture a PSA display, polymerizable compounds contained in the LC medium are polymerized or crosslinked by in-situ polymerization between the substrates of the LC display in the LC medium while optionally applying a voltage to the electrodes (when one compound contains two or more polymerizable groups).

[0329] The structure of the PSA display according to the present invention corresponds to the conventional configuration of a PSA display as described in the prior art cited at the beginning. A configuration without protrusions is preferred, and in particular, it is preferred that the electrodes on the color filter side are not structured, and only the electrodes on the TFT side have slits. A particularly suitable and preferred electrode structure for PS-VA displays is described, for example, in U.S. Patent Application Publication No. 2006 / 0066793.

[0330] A preferred PSA-type LC display of the present invention includes the following: A first substrate comprising a pixel electrode defining a pixel region, which is connected to a switch element placed in each pixel region and may have a microslit pattern, and a first orientation layer optionally placed on the pixel electrode; A second substrate comprising a common electrode layer which may be placed on the entire portion of the second substrate facing the first substrate, and an optional second orientation layer; • An LC layer disposed between a first substrate and a second substrate, comprising an LC medium layer containing a polymerizable component comprising one or more compounds of formula R, and a liquid crystal host containing the components described above and below (however, the polymerizable component may be polymerized).

[0331] The first and / or second orientation layers control the orientation direction of the LC molecules in the LC layer. For example, in a PS-VA display, the orientation layers are selected so that the LC molecules are homeotropically (or perpendicularly) oriented (i.e., perpendicular to the surface) or tilted. Such orientation layers may contain, for example, polyimide, which may be rubbed or prepared by a photo-alignment method.

[0332] An LC layer containing an LC medium can be placed between display substrates using methods commonly used in display manufacturing, such as the so-called liquid crystal drop (ODF) method. The polymerizable components of the LC medium are then polymerized, for example, by UV photopolymerization. Polymerization can be carried out in one or more steps.

[0333] The PSA display may include further elements such as a color filter, a black matrix, a passivation layer, an optical retardation layer, and transistor elements for addressing individual pixels, all of which are known to those skilled in the art and can be used without exhibiting any patentable skills.

[0334] Electrode structures can be designed by those skilled in the art according to the type of display. For example, multi-domain orientation of LC molecules can be induced by providing electrodes with slits and / or ridges or protrusions to generate two, four or more different tilt orientation directions for PS-VA displays.

[0335] Upon polymerization, polymerizable compounds form crosslinked polymers, resulting in a certain pretilling of LC molecules within the LC medium. While we do not wish to be bound by any particular theory, it is thought that at least a portion of the crosslinked polymer formed by the polymerizable compounds undergoes phase separation or precipitation from the LC medium, forming a layer of polymer on the substrate or electrode or an orientation layer provided thereon. Microscopic measurements (SEM and AFM, etc.) confirmed that at least a portion of the formed polymer accumulates at the LC / substrate interface.

[0336] Polymerization can be carried out in a single step. Alternatively, polymerization can be performed in the first step while applying an arbitrary voltage to generate a pre-tilt angle, and then in the second polymerization step, the compounds that did not react in the first step are polymerized or crosslinked without applying a voltage ("final curing").

[0337] A suitable and preferred polymerization method is, for example, thermal or photopolymerization, preferably photopolymerization, and particularly UV-induced photopolymerization, which can be achieved by exposing a photopolymerizable compound to UV irradiation.

[0338] One or more polymerization initiators are optionally added to the LC medium. Suitable conditions for polymerization and suitable types and amounts of initiators are known to those skilled in the art and are described in the literature. For example, commercially available photopolymerization initiators Irgacure 651 (registered trademark), Irgacure 184 (registered trademark), Irgacure 907 (registered trademark), Irgacure 369 (registered trademark), or Darocure 1173 (registered trademark) (Ciba) are suitable for free radical polymerization. When polymerization initiators are used, the proportion of the initiator is preferably 0.001 to 5% by weight, and particularly preferably 0.001 to 1% by weight.

[0339] Furthermore, the polymerizable compounds according to the present invention are also suitable for polymerization without an initiator, which brings notable advantages such as lower material costs and, in particular, less contamination of the LC medium due to the amount of residual initiator or its degradation products. Thus, polymerization can be carried out without adding an initiator. Therefore, in a preferred embodiment, the LC medium does not contain a polymerization initiator.

[0340] Furthermore, the LC medium may contain one or more stabilizers to prevent undesirable spontaneous polymerization of RM during storage or transport, for example. Suitable types and amounts of stabilizers are known to those skilled in the art and are described in the literature. For example, commercially available stabilizers from the Irganox® series (Ciba), such as Irganox® 1076, are particularly suitable. When stabilizers are used, the proportion of the stabilizer is preferably 10 to 500,000 ppm, and particularly preferably 50 to 50,000 ppm, based on the total amount of RM or polymerizable components (component P).

[0341] The polymerizable compound of formula P exhibits particularly good UV absorption in a method for preparing a PSA display that includes one or more of the following features, and is therefore particularly suitable for that method. The polymerizable medium is exposed to UV light within the display in a two-step process that includes a first UV exposure step ("UV-1 step") to generate a tilt angle and a second UV exposure step ("UV-2 step") to complete polymerization. The polymerizable medium is exposed within the display to UV light generated by an energy-saving UV lamp (also known as a "green UV lamp"). These lamps are characterized by relatively low intensity in the 300-380 nm absorption spectrum (1 / 100 to 1 / 10 of conventional UV lamps) and are preferably used in the UV2 step, but may be optionally used in the UV1 step if it is necessary to avoid high intensity. To avoid exposure to short-wavelength UV light in the PS-VA process, the polymerizable medium is exposed within the display to UV light generated by a UV lamp having an emission spectrum shifted to longer wavelengths (preferably 340 nm or longer).

[0342] Using lower intensity UV light or shifting to longer wavelength UV light will protect organic layers from damage that can be caused by UV light.

[0343] Preferred embodiments of the present invention relate to a method for preparing the PSA displays described above and below, and include one or more of the following features: The polymerizable LC medium is exposed to UV light in two steps, comprising a first UV exposure step ("UV-1 step") to generate a tilt angle and a second UV exposure step ("UV-2 step") to complete polymerization. • A polymerizable LC medium is subjected to a 0.5 mW / cm² wavelength range of 300-380 nm. 2 ~10mW / cm 2 The patient is exposed to UV light generated by a UV lamp having an intensity of (preferably, this UV lamp is used in the UV2 step, and optionally in the UV1 step as well). The polymerizable LC medium is exposed to UV light having a wavelength of 340 nm or higher, preferably 400 nm or lower.

[0344] This preferred method can be implemented, for example, by using a desired UV lamp or by using bandpass filters and / or cutoff filters that substantially transmit UV light having the desired wavelength and substantially block light having the undesired wavelength. For example, if irradiation with UV light with a wavelength λ of 300-400 nm is desired, UV exposure can be implemented using a wide bandpass filter that substantially transmits wavelengths λ greater than 300 nm and less than 400 nm. If irradiation with UV light with a wavelength λ greater than 340 nm is desired, UV exposure can be implemented using a cutoff filter that substantially transmits wavelengths λ greater than 340 nm.

[0345] "Substantially transmit" means that the filter transmits most, preferably at least 50%, of the incident light of the desired wavelength. "Substantially block" means that the filter does not transmit most, preferably at least 50%, of the incident light of the undesired wavelength. "Desired (undesired) wavelength" means, for example, wavelengths within (outside) a given range of λ in the case of a bandpass filter, and wavelengths above (below) a given value of λ in the case of a cutoff filter.

[0346] This preferred method enables the manufacture of displays using longer wavelength UV light, thereby reducing or avoiding the harmful and damaging effects of the short-wavelength components of UV light.

[0347] UV irradiation energy is generally between 6 and 100 J, depending on the conditions of the manufacturing process.

[0348] Preferably, the LC medium according to the present invention comprises essentially a polymerizable component P) containing a polymerizable compound of formula R as described above and below, or one or more polymerizable compounds of formula P, an LC host mixture, and an optically active component containing one or more chiral dopants. However, the LC medium may preferably additionally contain one or more further components or additives selected without limitation from the list including comonomers, polymerization initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricants, dispersants, hydrophobic agents, adhesives, flow improvers, defoamers, deaeration agents, diluents, reactive diluents, auxiliary agents, colorants, dyes, pigments and nanoparticles.

[0349] An LC medium containing one, two, or three polymerizable compounds of formula P is particularly preferred.

[0350] Preferably, the proportion of the compound of formula P in the LC medium is greater than 0% but less than 5%, very preferably greater than 0% but less than 1%, and most preferably 0.01 to 0.5%.

[0351] The liquid crystal mixture according to the present invention is preferably nematic at a temperature of -20°C or lower, preferably -30°C or lower, and very preferably -40°C or lower.

[0352] The liquid crystal medium according to the present invention is advantageous in that it preferably has a nematic phase with a temperature range of -20°C or lower to 70°C or higher, particularly preferably -30°C or lower to 80°C or higher, and very particularly preferably -40°C or lower to 85°C or higher.

[0353] In preferred embodiments, the medium of the present invention has a transparency point of 80°C or higher, preferably 82°C or higher, more preferably 85°C or higher, and particularly 87°C or higher.

[0354] In a first preferred embodiment, the medium of the present invention has a transparency point of 110°C or higher, preferably 115°C or higher, more preferably 118°C or higher, and particularly 120°C or higher.

[0355] In preferred embodiments, the liquid crystal mixture of the present invention has a dielectric anisotropy Δε of -2.0 to -6.0, preferably -3.2 to -5.5, and particularly -3.7 to -4.8.

[0356] The rotational viscosity γ1 at 20°C is preferably in the range of 100 to 350 mPas, more preferably 200 to 300 mPa·s.

[0357] The medium of the present invention contains the compound of formula I in a concentration ranging from 0.1% to 10%, preferably 0.5% to 8%, more preferably 1% to 7%, and very preferably 1.5% to 6%.

[0358] Preferred embodiments, either individually or in combination with each other, are as follows (acronyms are explained in Table D below): The medium preferably includes the following:

[0359] · A mixture containing one or more compounds of formula IIA, more preferably compounds of IIA-10, very preferably one or more compounds of compound CCY-n-Om, particularly CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and / or CCY-5-O2, preferably in a total concentration of less than 10%, preferably less than 5%, more preferably less than 1%, or in the range of 0% to 10%, more preferably 0.1% to 8%, particularly preferably 0.2% to 5%, or containing no compounds of formula IIA at all. and / or,

[0360] One or more compounds of formula IIB, preferably selected from compounds of formula IIB-10 and IIB-2, and very preferably one or more compounds selected from compounds PY-1-O4, PY-2-O2, PY-3-O2, PY-4-O2, CPY-2-O2, CPY-3-O2 and CPY-5-O2, are included in a total concentration preferably in the range of 5% to 40%, more preferably 7% to 30%, and particularly preferably 8% to 35%. and / or,

[0361] The compound contains one or more compounds of formula IIB-2, preferably selected from PY-1-O4, PY-2-O2, PY-3-O2, and PY-4-O2, in a total concentration of preferably 5% to 25%, more preferably 10% to 20%, and particularly preferably 12% to 18%. and / or,

[0362] • Contains one or more compounds of formula IIB-10, preferably selected from CPY-2-O2, CPY-3-O2, and CPY-5-O2, in a total concentration preferably in the range of 3% to 25%, more preferably 5% to 20%, and particularly preferably 7% to 14%. and / or,

[0363] • Contains one or more compounds of formula IIC in a total concentration preferably in the range of 1% to 10%, more preferably 2% to 8%, and particularly preferably 3% to 6%. and / or,

[0364] • Contains one or more compounds of formula IIC in a total concentration preferably in the range of 10% to 30%, more preferably 15% to 28%, and particularly preferably 20% to 26%. and / or,

[0365] The compound contains one or more compounds of formula IID, preferably one or more compounds selected from compounds of formula IID-4 and IID-10, in a total concentration preferably in the range of 1% to 15%, more preferably 3% to 13%, and particularly preferably 5% to 11%. and / or,

[0366] - One or more compounds of formula III, preferably compounds of formula III-2 and / or III-3, more preferably compounds of formula III-2-6 and / or III-3, in particular one or more compounds of B(S)-nO-Om and / or COB(S)-n-Om, very specifically B(S)-2O-O4, B(S)-2O-O5, B(S)-2O-O6, and / or COB(S)-2-O4, preferably in a total concentration of 1% to 20%, more preferably 2% to 17%, very preferably 4% to 15%; further optionally one or more compounds of formula III-1, preferably III-1-6, in particular B-2O-O5, in a total concentration of 1% to 15%, more preferably 2% to 10%, very preferably 4% to 8%. and / or,

[0367] • Contains one or more compounds of formula IV, preferably in a total concentration ranging from 5% to 25%, more preferably 6% to 20%, and particularly preferably 7% to 18%. and / or,

[0368] • Contains one or more compounds of formula IV-2, preferably compounds of formula IV-2-1 and / or IV-2-2, particularly compound CC-3-O1, in a total concentration preferably in the range of 1% to 15%, more preferably 3% to 12%, and very preferably 6% to 10%. and / or,

[0369] The compound of formula CC-3-V1 and / or CC-4-V1 is contained in a total concentration ranging from 1 to 10%, more preferably 2% to 9%, and particularly preferably 3% to 8%. and / or

[0370] • Contains one or more compounds of formula IV-3, preferably a compound of formula IV-3-1, more preferably a compound of CC-3-V and / or CC-4-V, in a total concentration preferably in the range of 5% to 20%, more preferably 10% to 18%, and very preferably 12% to 16%. and / or,

[0371] • Contains one or more compounds of formula IVa, more preferably compounds of formula IVa-2, particularly CP-3-O2, in a total concentration ranging from 0.5% to 8%, more preferably 1% to 6%, and very preferably 2% to 5%. and / or,

[0372] The mixture contains one or more compounds of formula V, more preferably selected from formulas V-2-1 and V-2-2, very preferably a compound of formula V-2-2, and optionally a compound of formula V-2-1, preferably a compound of formula V-2-2, in a total concentration of 2% to 20%, more preferably 4% to 14%, very preferably 6% to 12%, and further optionally a compound of formula V-2-1, in a total concentration of 1% to 10%, more preferably 2% to 8%, very preferably 3% to 7%, and further optionally one or more compounds of formula V-4, preferably a compound of formula V-4-1, in a total concentration of 1% to 10%, more preferably 2% to 8%, very preferably 3% to 7%. and / or,

[0373] The compound comprises one or more compounds selected from formulas V-1-1 and V-1-6, particularly CCC-nm and / or CCC-nV, more specifically CCC-3-V and / or CCC-VV, preferably in a total concentration ranging from 1% to 10%, more preferably 2% to 8%, and very preferably 3% to 6%. and / or,

[0374] The compound comprises one or more compounds of formula VI, preferably compounds of formula VI-1, preferably compounds selected from compounds of formulas VI-1-1, VI-1-4, VI-1-20, and VI-1-21, in a total concentration of preferably 1% to 25%, more preferably 2% to 20%, and very preferably 3% to 20%. and / or,

[0375] The compound contains one or more compounds of formula VI, preferably selected from compounds of formula VI-1, preferably VI-1-1, VI-1-4, VI-1-20, and VI-1-21, in a total concentration of preferably 1% to 25%, more preferably 2% to 20%, and very preferably 3% to 20%. and / or,

[0376] The compound comprises one or more compounds of formula VI-1-1 and one or more compounds selected from the compounds of formula VI-1-20 and VI-1-21, preferably in a total concentration of 5% to 25%, more preferably 8% to 22%, and very preferably 12% to 18%. and / or,

[0377] • Contains one or more compounds selected from the compounds of formula VI-1-4, preferably in a total concentration ranging from 1% to 12%, more preferably 2% to 9%, and very preferably 3% to 6%.

[0378] The compound comprises one or more compounds of formula VI-1-1, one or more compounds selected from the compounds of formula VI-1-20 and VI-1-21, and one or more compounds of formula VI-1-4, preferably in a total concentration ranging from 8% to 30%, more preferably 12% to 25%, and very preferably 15% to 22%. and / or,

[0379] The compound contains one or more compounds of formula VIII, preferably selected from compounds of formula VIII-3, more preferably from compounds of formula VIII-3a and VIII-3c, in a total concentration of preferably 2% to 20%, more preferably 5% to 15%, and very preferably 8% to 10%. and / or,

[0380] The compound contains one or more compounds of formula CL, more preferably compounds of formula CL-3 or CL-4, very preferably compounds selected from CLP-Vm, CLP-V-Om, CLP-nm, CLP-n-Om, and CLU-nF (where n and m are independently 1, 2, 3, 4, 5, and 6), preferably in a total concentration ranging from 0.1% to 5%, more preferably 0.2% to 3%, and very preferably 0.3% to 2%. and / or,

[0381] The compound contains one or more compounds of formula VIII, preferably selected from compounds of formula VIII-3, more preferably from compounds of formula VIII-3a and VIII-3c, in a total concentration of preferably 2% to 20%, more preferably 5% to 15%, and very preferably 8% to 10%. and / or,

[0382] • Contains 0.1% to 3% of compound PPGU-3-F and / or PPGU-(C5)-F. and / or,

[0383] • Contains one or more compounds of formula ST-16 in a total concentration ranging from 0.1% to 1%, preferably 0.2% to 0.8%, and more preferably 0.3% to 0.5%. and / or,

[0384] • Contains 0.1-3% of 2-(4-methylphenyl)-6-propylnaphthalene: [ka] and / or,

[0385] • Contains 0.1-3% of the compound 3-fluoro-4'-alkyl-4-(naphthalene-2-yl)-1,1'-biphenyl: [ka] (In the formula, alkyl is methyl, ethyl, n-propyl, n-butyl, n-pentyl, or n-hexyl, preferably n-propyl)

[0386] and / or, • Contains 0.1% to 3% of the compound 3-fluoro-4'-alkyl-4-[4-(naphthalene-2-yl)phenyl]-1,1'-biphenyl: [ka] (In the formula, alkyl is methyl, ethyl, n-propyl, n-butyl, n-pentyl, or n-hexyl, preferably n-propyl).

[0387] The liquid crystal medium according to the present invention has a high voltage retention rate in liquid crystal cells.

[0388] Generally, liquid crystal media with a low address voltage or threshold voltage exhibit a lower voltage retention rate than those with a high address voltage or threshold voltage, and vice versa.

[0389] As used herein, the term “dielectrically positive compound” refers to a compound with a Δε greater than 1.5, the term “dielectrically neutral compound” refers to a compound with a Δε between -1.5 and 1.5, and the term “dielectrically negative compound” refers to a compound with a Δε less than -1.5. The dielectric anisotropy of a compound is determined by dissolving 10% of the compound in a liquid crystal host and measuring the capacitance of the mixture obtained in at least one test cell with a layer thickness of 20 μm, each with homeotropic and homogeneous surface orientations, at 1 kHz. The measurement voltage is typically 0.5 V to 1.0 V, but is always lower than the capacitance threshold of the liquid crystal mixture under consideration.

[0390] All temperature values ​​shown in this invention are in °C.

[0391] The mixtures according to the present invention are suitable for all VA-TFT applications, such as VAN, MVA, (S)-PVA, ASV, PSA (polymer-retaining VA), and PS-VA (polymer-stabilizing VA). They are also suitable for IPS (in-plane switching) and FFS (fringe-field switching) applications with negative Δε, particularly UB-FFS.

[0392] It goes without saying to those skilled in the art that the VA, IPS, or FFS mixture of the present invention may also include, for example, compounds in which H, N, O, Cl, and F are substituted with the corresponding isotopes.

[0393] The compounds of the present invention can be synthesized by known methods described in the literature (e.g., standard works such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Thieme-Verlag, Stuttgart, etc.) or similar methods under known reaction conditions suitable for the above reaction. Variations known to themselves, though not mentioned herein, can also be used herein. In particular, they can be prepared by methods described in or similar to the following reaction schemes. Further methods for preparing the compounds of the present invention can be obtained from the examples.

[0394] Other mesogenic compounds not explicitly mentioned above may also be optionally and advantageously used in media according to the present invention. Such compounds are known to those skilled in the art.

[0395] In the present invention and the following examples, the structure of the liquid crystal compound is indicated by an acronym, and its conversion to a chemical formula is performed according to Tables A to C below. m H 2m+1 , C n H 2n+1 , and C l H 2l+1 or C m H 2m-1 , C n H 2n-1 and Cl H 2l-1 These are linear alkyl or alkylene groups having n, m, and l carbon atoms, respectively. Preferably, n, m, and l are 1, 2, 3, 4, 5, 6, or 7, independently of each other. Table A shows the codes of the ring elements of the core of the compound, Table B lists the bridging units, and Table C lists the meanings of the symbols of the left- and right-end groups of the molecule. The acronym consists of the code of the ring element having any linking group, followed by a first hyphen and the code of the left-end group, and a second hyphen and the code of the right-end group. Table D shows structural examples of the compound along with their respective abbreviations.

[0396] Table A: Ring elements [Table 1]

[0397] [Table 2]

[0398] [Table 3]

[0399] Table B: Crosslinking Units [Table 4]

[0400] Table C: Terminal groups [Table 5] [Table 6]

[0401] In the table, n and m are integers, and the three dots "..." are spaces for other abbreviations from this table.

[0402] Apart from the compounds of formulas I, IIA, IIB, IIC and / or IID, IVa, IVb and V, the mixtures of the present invention optionally include one or more of the compounds described below.

[0403] The following abbreviations will be used. (n, m, k, and l are each an integer independently of each other, preferably 1 to 9, preferably 1 to 7, k and l may be 0, preferably 0 to 4, more preferably 0 or 2, most preferably 2, n is preferably 1, 2, 3, 4, or 5, in combination "-nO-", it is preferably 1, 2, 3, or 4, more preferably 2 or 4, m is preferably 1, 2, 3, 4, or 5, in combination "-Om", it is preferably 1, 2, 3, or 4, more preferably 2 or 4. The combination "-lVm" is preferably "2V1".

[0404] Table D [Table 7] [Table 8] [Table 9] [Table 10] [Table 11] [Table 12] [Table 13] [Table 14] Table 15 Table 16 Table 17 Table 18 Table 19 Table 20 Table 21 Table 22 Table 23 Table 24 Table 25 Table 26 Table 27 Table 28 [Table 29]

[0405] Table E Table E shows exemplary reactive mesogenic compounds that may be used in the LC medium according to the present invention. [Table 30] [Table 31] [Table 32] [Table 33] [Table 34] [Table 35] [Table 36] [Table 37] [Table 38] [Table 39] [Table 40] [Table 41] [Table 42] [Table 43] [Table 44] [Table 45] [Table 46] [Table 47]

[0406] In preferred embodiments, the mixture of the present invention comprises one or more polymerizable compounds, preferably selected from polymerizable compounds of formulas RM-1 to RM-182. Among these, compounds RM-1, RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48 , RM-52, RM-54, RM-57, RM-58, RM-64, RM-74, RM-76, RM-88, RM-91, RM-102, RM-103, RM-1 09, RM-116, RM-117, RM-120, RM-121, RM-122, RM-139, RM-140, RM-142, RM-143, RM-145 , RM-146, RM-147, RM-149, RM-156 to RM-163, RM-169, RM-170 and RM-171 to RM-184 are particularly preferred. [Examples]

[0407] The present invention will be described in detail by the following non-limiting embodiments. The following abbreviations and symbols are used: [Table 48]

[0408] Unless otherwise explicitly stated, all concentrations in this application are cited in weight percent and refer to the corresponding mixture as a whole, consisting of all solid or liquid crystal components, without the presence of a solvent.

[0409] Unless explicitly stated otherwise, all temperature values ​​expressed in this application, such as the melting point T(C,N), the transition from the smectic (S) phase to the nematic (N) phase T(S,N), and the transparency point T(N,I), are cited in degrees Celsius (°C). Mp is the melting point, and cl.p. is the transparency point. Furthermore, C is the crystalline state, N is the nematic phase, S is the smectic phase, and I is the isotropic phase. The data between these symbols represents the transition temperature.

[0410] All physical properties are determined or have been determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals," published November 1997 by Merck, Germany, applicable at a temperature of 20°C, with Δn being 589 nm and Δε being 1 kHz unless otherwise explicitly indicated.

[0411] In this invention, the term "threshold voltage" refers to the capacitance threshold (V0) (also known as the Fredericks threshold) unless explicitly stated otherwise. Furthermore, in the examples, although generally typical, 10% relative contrast (V0) is used. 10 The optical threshold for ) may also be indicated.

[0412] Unless otherwise stated, the polymerization process of polymerizable compounds in the PSA display described above is carried out at a temperature in which the LC medium exhibits a liquid crystal phase, preferably a nematic phase, and most preferably at room temperature.

[0413] Unless otherwise specified, the preparation of test cells and the measurement of their electro-optical properties and other characteristics shall be carried out in the manner or similarly described below.

[0414] The display used for measuring the capacitance threshold voltage consists of two planar parallel glass outer plates spaced 25 μm apart, each having an electrode layer on the inside and an unrubbed polyimide orientation layer on the top that provides homeotropic orientation of liquid crystal molecules.

[0415] The display or test cell used to measure the tilt angle consists of two planar parallel glass outer plates spaced 4 μm apart, each with an electrode layer on the inside and a polyimide orientation layer on top, however, the two polyimide layers are rubbed in opposite parallel directions to each other, resulting in homeotropic edge orientation of liquid crystal molecules.

[0416] Polymerizable compounds are polymerized by irradiating them with UV light of a specified intensity for a predetermined time within a display or test cell, while simultaneously applying a voltage to the display (typically 10V to 30V AC, 1kHz). In the examples, unless otherwise indicated, fluorescent lamps and 0-20mW / cm² are used. 2 The intensity is used for polymerization. The intensity is measured using a standard meter (Ushio Accumulate UV meter with a central wavelength of 313 nm).

[0417] Transmittance measurements are performed in a test cell with a fishbone electrode layout (Merck KGaA, Japan; 1-pixel fishbone electrode (ITO, 10 × 10 mm, fishbone angle 47.7° with 3 μm line / 3 μm space), 3.2 μm cell gap, AF glass, tilt angle 1°).

[0418] Storage stability (LTS) of the medium in bulk according to the present invention at a predetermined temperature T. bulkThe stability is determined by visual inspection. 2g of the material is filled into a suitably sized sealed glass container (bottle) and placed in a refrigerator at a specified temperature. The bottle is checked at specified time intervals for the occurrence of the smectic phase or crystallization. Two bottles are stored for all materials and each temperature. If the appearance of crystallization or the smectic phase is observed in at least one of the two corresponding bottles, the test is terminated, and the time of the last inspection before the occurrence of a higher phase is recorded as the storage stability for each.

[0419] Mixture comparative example C1 [Table 49]

[0420] Mixture Example M1 [Table 50]

[0421] Mixture Example M2 [Table 51]

[0422] Mixture Example M3 [Table 52]

[0423] Mixture Example M4 [Table 53]

[0424] Mixture Example M5 [Table 54]

[0425] Mixture Example M6 [Table 55]

[0426] Mixture Example M7 [Table 56]

[0427] Mixture Example M8 [Table 57]

[0428] Mixture Example M9 [Table 58]

[0429] Mixture Example M10 [Table 59]

[0430] Mixture Example M11 [Table 60]

[0431] Mixture Example M12 [Table 61]

[0432] polymerizable mixture Polymerizable mixtures P1 to P11 are prepared by adding reactive mesogens (RM) selected from the group of compounds of formula RM-1, RM-17, RM-35, RM-64, and RM-171 to the nematic mixtures shown in Table 1 in the amounts (%RM) shown in Table 1. [Table 62]

[0433] Table 1: Polymerizable mixture [Table 63]

[0434] Mixture Example P11 Polymerizable mixture P11 consists of 99.434% of mixture example M1, 0.300% of RM-1, 0.200% of RM-145, 0.050% of RM-163, 0.001% of Irganox® 1076, and 0.015% of compound ST-3a-1. [ka]

Claims

1. One or more equations I: 【Chemistry 1】 (In the formula, R １１ and R １２ H represents the same or different linear alkyl or alkoxy having 1 to 15 carbon atoms each, linear alkenyl or alkenyloxy having 2 to 15 carbon atoms each, or branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 carbon atoms each, where one or more CH ２ The groups are independent of each other, and the oxygen atoms are not directly adjacent to each other. 【Chemistry 2】 -CH=CH-, -C≡C-, -CF ２ O-, -OCF ２ They may be substituted with -, -O-, -CO-O-, or -O-CO- respectively, and one or more H atoms may be substituted with halogens. L １１ , L １２ , L １３ , L １４ are the same or different and each represents H, F, Cl, CH ３ , CF ３ or CHF ２ , and at least one of L １１ , L １２ , L １３ , L １４ represents F, Cl, CH ３ , CF ３ or CHF ２ ) A liquid crystal medium containing the compound, A liquid crystal medium having negative dielectric anisotropy.

2. The aforementioned medium is based on formulas IIA, IIB, IIC, and IID: 【Transformation 3】 (In the formula, R ２Ａ , R ２Ｂ , R ２Ｃ and R ２Ｄ H represents a linear alkyl or alkoxy having 1 to 15 carbon atoms each, a linear alkenyl or alkenyloxy having 2 to 15 carbon atoms each, or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 carbon atoms each, where one or more CH ２ The groups are independent of each other, and the oxygen atoms are not directly adjacent to each other. 【Chemistry 4】 -CH=CH-, -C≡C-, -CF ２ O-, -OCF ２ They may be substituted with -, -O-, -CO-O-, or -O-CO- respectively, and one or more H atoms may be substituted with halogens. L １ and L ２ F, Cl, CF are independent of each other. ３ or CHF ２ This represents, Y is H, F, Cl, CF ３ CHF ２ or CH ３ This represents, Z ２ Z ２Ｂ and Z ２Ｄ These are independent of each other, single bonds, -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -, -COO-, -OCO-, -C ２ F ４ -, -CF=CF- or -CH=CHCH ２ Represents O-, X is O or CH ２ Represents (O) represents oxygen or a single bond. p represents 0, 1, or 2. q represents 0 or 1, (v represents an integer between 1 and 6) The liquid crystal medium according to claim 1, comprising one or more compounds selected from the group of compounds.

3. The aforementioned medium contains one or more compounds of formula I, wherein the group L １１ , L １２ , L １３ and L １４ One or two of these represent F, and the base L １１ , L １２ , L １３ and L １４ The liquid crystal medium according to claim 1 or 2, wherein the remaining group represents H.

4. The aforementioned medium contains one or more formulas III: 【Transformation 5】 (In the formula, R ３１ and R ３２ Each represents an alkyl or alkoxy group having H, 1 to 15 C atoms, and one or more CH groups. ２ The groups are independent of each other, and the oxygen atoms are not directly adjacent to each other. 【Transformation 6】 -CH=CH-, -C≡C-, -CF ２ O-, -OCF ２ They may be substituted with -, -O-, -CO-O-, or -O-CO- respectively, and one or more H atoms may be substituted with halogens. A ３１ Each instance of these symbols represents, independently of each other, the following: a) A 1,4-cyclohexylene or 1,4-cyclohexenylene group, where one or two non-adjacent CH groups ２ The group may be substituted with -O- or -S-. b) A 1,4-phenylene group, where one or two CH groups may be substituted with N, or c) A group selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl, and fluorene-2,7-diyl, Groups a), b), and c) may be monosubstituted or polysubstituted with halogen atoms. Z ３１ Each instance of these is independent of each other: -CO-O-, -O-CO-, -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -ien-CH ２ -ien-CH ２ CH ２ -, - (CH ２ ) ４ -, -CH=CH-CH ２ O-, -C ２ F ４ -ien-CH ２ CF ２ -, -CF ２ CH ２ -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or single bond, L ３１ and L ３２ F, Cl, CF are independent of each other. ３ or CHF ２ This represents, W represents O or S, n is 0, 1, or 2. A liquid crystal medium according to any one of claims 1 to 3, comprising the compound.

5. The aforementioned medium is a medium of formulas BC, CR, PH-1, and PH-2: 【Transformation 7】 (In the formula, R Ｂ１ , R Ｂ２ , R ＣＲ１ , R ＣＲ２ , R Ｐ１ , and R Ｐ２ Each represents an alkyl or alkoxy group having H, 1 to 15 C atoms, where one or more CH groups are independent of each other. ２ The groups are independent of each other, and the oxygen atoms are not directly adjacent to each other. 【Transformation 8】 —CH=CH—, —C≡C—, —CF ２ O—, —OCF ２ —, —O—, —CO—O— or —O—CO— may each be substituted, and one or more H atoms may be substituted with halogen, c is 0, 1, or 2. A liquid crystal medium according to any one of claims 1 to 4, comprising one or more compounds selected from the group of compounds.

6. The aforementioned medium contains one or more formulas IV: 【Chemistry 9】 (In the formula, R ４１ This represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms. R ４２ (This represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.) A liquid crystal medium according to any one of claims 1 to 5, comprising the compound.

7. The aforementioned medium contains one or more formulas V: 【Chemistry 10】 (In the formula, R ５１ , R ５２ This represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkoxyalkyl group, alkenyl group, or alkenyloxy group, each having 2 to 7 carbon atoms, and being identical or different. 【Chemistry 11】 Z ５１ and Z ５２ are the same or different and each represents -CH ２ -CH ２ -, -CH ２ -O-, -CH=CH-, -C≡C-, -COO- or a single bond, n is either 1 or 2. A liquid crystal medium according to any one of claims 1 to 6, comprising the compound (except one or more compounds of formula I of claim 1).

8. The aforementioned medium is given by formula VI: 【Chemistry 12】 (In the formula, R ６１ and R ６２ H represents a linear alkyl or alkoxy having 1 to 15 carbon atoms, a linear alkenyl or alkenyloxy having 2 to 15 carbon atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 carbon atoms, where one or more CH ２ The groups are independent of each other, and the oxygen atoms are not directly adjacent to each other. 【Chemistry 13】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O-, or -O-CO- may be substituted, and one or more H atoms may be substituted with halogens. X ６１ , X ６２ , X ６３ , X ６４ , X ６５ , and X ６６ These represent the same or different, H or F. Z ６１ and Z ６２ They are the same or different, CH ２ CH ２ (or represents a single bond) A liquid crystal medium according to any one of claims 1 to 7, comprising one or more compounds of formula IIC (except for compounds of formula IIC).

9. The aforementioned medium is given by formula VIII: 【Chemistry 14】 (In the formula, R ８１ and R ８２ This represents the same or different H, halogen, CN, SCN, a linear alkyl or alkoxy having 1 to 15 carbon atoms, a linear alkenyl or alkenyloxy having 2 to 15 carbon atoms, or a branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 carbon atoms, and one or more CH ２ The groups are independent of each other, and the oxygen atoms are not directly adjacent to each other. 【Chemistry 15】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O-, or -O-CO- may be substituted, and one or more H atoms may be substituted with halogens. A ０ A ８１ , and A ８２ These are phenylene-1,4-diyl (where one or two CH groups may be substituted with N, and one or more H atoms are halogens, CN, CH) independently of each other. ３ CHF ２ ,CH ２ F, CF ３ , OCH ３ , OCHF ２ or OCF ３ (may be substituted with), cyclohexane-1,4-diyl (where one or two non-adjacent CH4s) ２ The groups may be independently substituted with O and / or S, and one or more H atoms may be substituted with F), representing cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, Z ８１ and Z ８２ These are independent of each other, -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -, -CO-O-, -O-CO-, -C ２ H ４ -, -C ２ F ４ , -CF ２ CH ２ -ien-CH ２ CF ２ -, -CFHCFH-, -CFHCH ２ -ien-CH ２ CFH-, -CF ２ CFH-, -CFHCF ２ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C- or single bond, n represents 0, 1, 2, or 3. (m represents 0, 1, 2, or 3) A liquid crystal medium according to any one of claims 1 to 8, comprising one or more of the compounds.

10. A liquid crystal display comprising a liquid crystal medium according to any one of claims 1 to 9.

11. The liquid crystal display according to claim 10, wherein the display is a VA type, IPS type, or FFS type display.

12. The liquid crystal display according to claim 10 or 11, wherein the liquid crystal display is an LCoS display.

13. The liquid crystal display according to claim 12, wherein the liquid crystal display has an inorganic alignment layer.

14. A device comprising a liquid crystal display according to claims 10 to 13, wherein the device is an augmented reality eyewear, smart glasses, a virtual reality headset, a head-up display system, a head-mounted display, or a near-to-eye display.

15. A method for producing a liquid crystal medium according to any one of claims 1 to 9, comprising the step of mixing one or more compounds of formula I with one or more compounds selected from the group consisting of formulas IIA, IIB, IIC, and IID, optionally one or more mesogenic compounds or liquid crystal compounds, and optionally one or more additives.

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