WO2023094404A1 - Milieu de cristaux liquides et dispositif d'affichage à cristaux liquides - Google Patents

Milieu de cristaux liquides et dispositif d'affichage à cristaux liquides Download PDF

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Publication number
WO2023094404A1
WO2023094404A1 PCT/EP2022/082871 EP2022082871W WO2023094404A1 WO 2023094404 A1 WO2023094404 A1 WO 2023094404A1 EP 2022082871 W EP2022082871 W EP 2022082871W WO 2023094404 A1 WO2023094404 A1 WO 2023094404A1
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compounds
atoms
liquid
alkyl
weight
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PCT/EP2022/082871
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English (en)
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Tzu-Feng HSIA
Chi-Shun Huang
Kuang-Ting Chou
Jer-Lin Chen
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Merck Patent Gmbh
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    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
    • G02F1/13731—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on a field-induced phase transition
    • G02F1/13737—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on a field-induced phase transition in liquid crystals doped with a pleochroic dye
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    • C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
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    • C09K19/3001—Cyclohexane rings
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    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring

Definitions

  • the present invention relates to electro-optical devices and in particular energyefficient liquid crystal displays comprising a liquid-crystalline switchable layer containing one or more dichroic dyes in relatively small amounts, to liquid-crystalline media for use in said devices, and to the use of said dichroic dyes in liquid crystal displays to reduce light leakage and to improve the contrast ratio.
  • Liquid crystals have found widespread use since the first commercially usable liquid-crystalline compounds were found.
  • Liquid crystal displays are used in many areas for the display of information. LCDs are used both for direct-view displays and for projection-type displays.
  • TN LCDs have the disadvantage of a strong viewing-angle dependence of the contrast.
  • VA vertical aligned
  • the LC cell of a VA display contains a layer of an LC medium between two transparent electrodes, where the LC medium usually has a negative dielectric anisotropy.
  • the molecules of the LC layer are aligned perpendicular to the electrode surfaces (homeotropically) or have a tilted homeotropic alignment.
  • an electrical voltage to the two electrodes, a realignment of the LC molecules parallel to the electrode surfaces takes place.
  • IPS in-plane switching
  • IPS in-plane switching
  • the two electrodes are arranged on only one of the two substrates and preferably have intermeshed, comb-shaped structures.
  • an electric field which has a significant component parallel to the LC layer is thereby generated between them. This causes realignment of the LC molecules in the layer plane.
  • FFS far-field switching
  • FFS displays have been reported, see inter alia S.H. Jung et al., Jpn. J. Appl. Phys., Volume 43, No. 3, 2004, 1028, which contain two electrodes on the same substrate, one of which is structured in a combshaped manner and the other is unstructured.
  • a strong, so-called “fringe field” is thereby generated, i.e. a strong electric field close to the edge of the electrodes, and, throughout the cell, an electric field which has both a strong vertical component and also a strong horizontal component.
  • FFS displays have a low viewing-angle dependence of the contrast.
  • FFS displays usually contain an LC medium with positive dielectric anisotropy, and an alignment layer, usually of polyimide, which provides planar alignment to the molecules of the LC medium.
  • FFS displays can be operated as active-matrix or passive-matrix displays.
  • active-matrix displays individual pixels are usually addressed by integrated, nonlinear active elements, such as for example transistors, for example thin-film transistors ("TFTs"), while in the case of passive-matrix displays individual pixels are usually addressed by the multiplex method.
  • TFTs thin-film transistors
  • IPS in-plane switching
  • FFS fringe-field switching
  • HB- FFS High Brightness FFS
  • FFS displays have been described in S.H. Lee et al., Appl. Phys. Lett. 73(20), 1998, 2882-2883 and S.H. Lee et al., Liquid Crystals 39(9), 2012, 1141-1148, which have similar electrode design and layer thickness as FFS displays, but comprise a layer of an LC medium with negative dielectric anisotropy instead of an LC medium with positive dielectric anisotropy.
  • the LC medium with negative dielectric anisotropy can show a more favourable director orientation that has less tilt and more twist orientation compared to the LC medium with positive dielectric anisotropy, as a result of which these displays may have a higher transmission.
  • the displays further comprise an alignment layer, preferably of polyimide provided on at least one of the substrates that is in contact with the LC medium and induces planar alignment of the LC molecules of the LC medium.
  • These displays are also known as "Ultra Brightness FFS” (UB-FFS) mode displays. These displays require an LC medium with high reliability. Especially for monitor, mobile, video gaming and TV applications it is desirable to obtain favourably short response times, a wide viewing angle, low power consumption, a high transmittance and a suitably high contrast ratio of the LC displays.
  • the retardation may be lowered by reducing the cell gap and/or by decreasing the optical anisotropy of the LC medium to improve the dark state quality.
  • the elastic constants of the LC medium may however affect the operating voltage and the response time of the device.
  • An object of the present invention is therefore to provide electro-optical devices and in particular displays with a favourable electro-optical performance, in particular with a high contrast ratio and a good black state while at the same time enabling high brightness or a high transmittance in one optical state, a low threshold voltage, fast addressing times and a favourable reliability and stability, in particular at low temperatures and at high temperatures. It is a further object of the present invention to provide liquid-crystalline media which can give benefits in these displays and which are suitably advantageous to further optimise the displays. Further objects of the present invention are immediately evident to the person skilled in the art from the following detailed description.
  • a first aspect of the present invention provides an electro-optical device which comprises
  • each substrate is provided with an electrode structure or one of the substrates is provided with two electrode structures and the other substrate is not provided with an electrode, and
  • the switchable layer comprises a liquid-crystalline medium, wherein the liquid-crystalline medium comprises one or more dichroic dyes, and wherein the one or more dichroic dyes are contained in the medium in a total amount of 2.0% by weight or less.
  • the one or more dichroic dyes are provided in relatively small and limited yet effective amounts in the liquid-crystalline media to efficiently improve the dark state and the overall contrast of the devices and in particular displays, e.g. FFS, HB-FFS and especially LIB-FFS displays, without however affecting the desired device transmittance or brightness or only reducing the device transmittance or brightness to a minimal or even negligible extent.
  • display e.g. FFS, HB-FFS and especially LIB-FFS displays
  • energy-efficient electro-optical devices and in particular energy-efficient displays are provided which favourably exhibit a particularly high contrast and at the same time favourable brightness and fast response times.
  • a further aspect of the invention relates to liquid-crystalline media which comprise one or more dichroic dyes in a total amount of 2.0% by weight or less, preferably 1.0% by weight or less, and one or more compounds of formula I V- 1 in a total amount of at least 20% by weight, preferably at least 30% by weight, wherein in formula IV-1 R 41 and R 42 independently of each other, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C atoms.
  • these liquid-crystalline media are particularly suitable for use in the electro-optical devices according to the invention.
  • these media can give benefits in terms of achieving an improved dark state, while also favourably contributing to enabling low operating voltages, fast response times as well as reliability and stability also at low and high temperatures.
  • Another aspect of the invention relates to the use of one or more dyes and especially pleochroic dyes or one or more pigments, in particular of one or more dichroic dyes in a liquid-crystal switchable layer comprised in an electro-optical device to decrease light leakage and to improve the contrast ratio of the device.
  • halogen denotes F, Cl, Br or I, preferably F or Cl, and more preferably F.
  • all atoms also include their isotopes.
  • one or more hydrogen atoms (H) may be replaced by deuterium (D), which is particularly preferred in some embodiments; a high degree of deuteration enables or simplifies analytical determination of compounds, in particular in the case of low concentrations.
  • an alkyl radical and/or an alkoxy radical is taken to mean straight-chain or branched alkyl or respectively alkoxy. It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.
  • alkenyl may be straight-chain or branched. It is preferably straight-chain and has 2 to 10 C atoms. Accordingly, it denotes, in particular, vinyl, prop-1- or -2-enyl, but- 1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl, oct-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, non-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl, dec-1-, -2-,
  • an alkyl or alkenyl radical which is at least monosubstituted by halogen is preferably straight-chain, and halogen is preferably F or Cl.
  • halogen is preferably F.
  • the resultant radicals also include perfluorinated radicals.
  • the fluorine or chlorine substituent may be in any desired position, but is preferably in the o-position.
  • a mono- or polyfluorinated alkyl or alkoxy radical having 1 , 2 or 3 C atoms or a mono- or polyfluorinated alkenyl radical having 2 or 3 C atoms is particularly preferably F, Cl, CF 3 , CHF 2 , OCF 3 , OCHF 2 , OCFHCF 3 , OCFHCHF2, OCFHCHF2, OCF 2 CH 3 , OCF2CHF2, OCF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCF2CF2CHF2, OCFHCF 2 CF 3 ,
  • 1 ,4-cyclohexylene rings are depicted as follows: wherein the cyclohexylene rings are trans- 1 ,4-cyclohexylene rings.
  • Electro-optical devices according to the invention may adopt different optical states using electrical switching, where the application of voltage controls the switching.
  • These devices may be used as, for example, light shutters and optical intensity modulators, in particular liquid crystalbased light modulators, wherein the transmission of light can be reversibly changed.
  • the electro-optical devices are displays for displaying information, in particular active matrix addressed displays.
  • the liquidcrystal display is a TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, UB- FFS, PS-HB-FFS, SA-HB-FFS, polymer stabilised SA-HB-FFS, VA or PS-VA display, more preferably an IPS, FFS, HB-FFS or LIB-FFS display.
  • a switchable layer is arranged between two substrates such as to give an optical cell which is operable in different optical states and which may be switched or actuated electrically.
  • Suitable substrates are transparent substrates, which may preferably be made of glass or plastic.
  • Electrodes are provided on both substrates, in particular to provide a VA switching mode.
  • one or both substrates are provided with alignment or orientation layers, e.g. made of polyimide, to influence or set the alignment of the liquid-crystalline medium at the interface.
  • alignment or orientation layers e.g. made of polyimide
  • rubbed polyimide or photo-aligned polyimide as alignment layers, in particular rubbed polyimide for example in FFS type applications.
  • the electro-optical device comprises two polarizers, in particular two polarizer layers or polarization layers. Both absorptive and also reflective polarizers may be employed. Preference is given to the use of polarizers which are in the form of thin optical films.
  • the polarizers are preferably linear polarizers.
  • At least one optical retarder in particular at least one retardation layer, is provided in the device.
  • at least one optical retarder is present, more preferably two optical retarders.
  • retardation layers or plates may be used to compensate for phase dispersion so that a wider viewing angle is obtainable.
  • the liquid-crystalline medium in particular the liquidcrystalline medium contained in the switchable layer of the electro-optical device, comprises one or more dichroic dyes in a total amount of 2.0% by weight or less.
  • the total amount of the one or more dichroic dyes in the liquidcrystalline medium is 1.0% by weight or less. It is further preferred that the total amount of the one or more dichroic dyes in the liquid-crystalline medium is 0.5% by weight or less, more preferably 0.2% by weight or less.
  • a dichroic dye is taken to mean a light-absorbing compound in which the absorption properties are dependent on the orientation of the compound relative to the direction of polarization of the light.
  • a dichroic dye compound in accordance with the present invention typically has an elongated shape, i.e. the compound is significantly longer in one spatial direction, i.e. along the longitudinal axis, than in the other two spatial directions.
  • the dichroic dye absorbs, or respectively preferentially absorbs, light in one orientation so that light transmission may be modulated by changing the orientation of the dichroic dye.
  • liquid crystal host is doped with dichroic dye molecules in relatively small, limited amounts.
  • dye-doped LC media are used particularly preferably for FFS and LIB-FFS modes, however also other display modes as described above and below can be employed.
  • the dichroic dye compounds are present in the liquid-crystalline medium in solution.
  • the dichroic dye molecules as used according to the invention therefore preferably exhibit suitable and sufficient solubility in the liquid crystal host.
  • the dye compounds preferably also favourably contribute to the stability and reliability of the media.
  • Each of the one or more dichroic dyes is preferably present in the liquid-crystalline medium in a proportion of 0.002% by weight to 2.0% by weight, more preferably 0.003% by weight to 1.0% by weight, still more preferably 0.005% by weight to 0.5% by weight, even more preferably 0.01% by weight to 0.3% by weight, and particularly preferably 0.02% by weight to 0.2% by weight, based on the overall weight of the entire medium.
  • the one or more dichroic dyes are present in the liquid-crystalline medium overall in a total concentration which is in the range of from 0.003% by weight to 2.0% by weight, more preferably 0.004% by weight to 1.5% by weight, still more preferably 0.005% by weight to 1.0% by weight, yet more preferably 0.01% by weight to 0.5% by weight, even more preferably 0.02% by weight to 0.3% by weight, and particularly preferably 0.05% by weight to 0.2% by weight.
  • the concentration of the dye(s) is favourably chosen such that the proper performance of the obtained liquid-crystalline material is ensured, in particular in terms of the desired reduction of the light leakage in the dark state and the improved black image quality and overall contrast, while suitably maintaining other device properties such as response times, operating voltage and brightness.
  • the upper limit of the dye concentration is provided in particular in view of maintaining the bright state performance of the device such that transmittance is not affected or only to a minimal extent.
  • the one or more dichroic dyes may also be present in the liquid-crystalline medium in a total concentration which is in the range of from 2.0% by weight to 5.0% by weight, or even above 5.0% by weight and up to 10.0% by weight.
  • Dichroic dyes may preferably be selected from for example azo dyes, anthraquinones, thiophenolanthraquinones, methine compounds, azomethine compounds, merocyanine compounds, naphthoquinones, tetrazines, pyrromethene dyes, malononitrile dyes, nickel dithiolenes, (metal) phthalocyanines, (metal) naphthalocyanines and (metal) porphyrins, rylenes, in particular perylenes and terylenes, thiadiazole dyes, thienothiadiazole dyes, benzothiadiazoles, thiadiazoloquinoxalines, and diketopyrrolopyrroles.
  • azo dyes anthraquinones, thiophenolanthraquinones, methine compounds, azomethine compounds, merocyanine compounds, naphthoquinones, tetrazines, pyrrometh
  • azo compounds anthraquinones, thiophenolanthraquinones, benzothiadiazoles, in particular as described in WO 2014/187529 and in WO 2020/104563 A1, diketopyrrolopyrroles, in particular as described in WO 2015/090497, thiadiazoloquinoxalines, in particular as described in WO 2016/177449 and in WO 2020/104563 A1, and rylenes, in particular as described in WO 2014/090373.
  • the one or more dichroic dyes are selected from azo compounds, benzothiadiazoles and thiadiazoloquinoxalines.
  • the liquid-crystalline medium preferably comprises one, two, three, four, five, six, seven, eight, nine or ten different dichroic dyes, particularly preferably two, three, four, five or six dichroic dyes.
  • the medium contains at least three different dichroic dyes.
  • the absorption spectra of the dichroic dyes contained in the medium or respectively the switchable layer preferably complement one another in such a way that the impression of a black colour, or respectively a colour-neutral appearance, arises for the eye.
  • two or more, more preferably three or more dichroic dyes are used in the liquid-crystalline medium to preferably cover a large part of the visible spectrum.
  • the precise way in which a mixture of dyes which appears black or grey to the eye can be prepared is known in the art and is described, for example, in M. Richter, Einbowung in die Farbmetrik [Introduction to Colorimetry], 2nd Edition, 1981 , ISBN 3 11-008209-8, Walter de Gruyter & Co.
  • the setting of the colour location of a mixture of dyes is described in the area of colorimetry.
  • the spectra of the individual dyes are calculated taking into account the Lambert-Beer law to give an overall spectrum and converted into the corresponding colour locations and luminance values under the associated illumination, for example illuminant D65 for daylight, in accordance with the rules of colorimetry.
  • the position of the white point is fixed by the respective illuminant, for example D65, and is quoted in tables, for example in the reference above.
  • Different colour locations can be set by changing the proportions of the various dyes.
  • the medium and the switchable layer comprise one or more dichroic dyes which absorb light in the visible spectrum, which herein is defined as light having a wavelength of from 380 nm to 780 nm.
  • dichroic dyes which efficiently and effectively absorb green light.
  • the dichroic dyes provided in the medium and the switchable layer are preferably selected from the dye classes indicated in B. Bahadur, Liquid Crystals - Applications and Uses, Vol. 3, 1992, World Scientific Publishing, Section 11.2.1, and particularly preferably from the explicit compounds given in the table present therein.
  • Said dyes belong to the classes of dichroic dyes which are known in the art and have been described in the literature.
  • anthraquinone dyes are described in EP 34832, EP 44893, EP 48583, EP 54217, EP 56492, EP 59036, GB 2065158, GB 2065695, GB 2081736, GB 2082196, GB 2094822, GB 2094825, JP A 55-123673, DE 3017877, DE 3040102, DE 3115147, DE 3115762, DE 3150803 and DE 3201120, naphthoquinone dyes are described in DE 3126108 and DE 3202761, azo dyes in EP 43904, DE 3123519, WO 82/2054, GB 2079770, JP-A 56-57850, JP-A 56-104984, US 4308161, US 4308162, US 4340973, T.
  • the compounds described herein are either known or can be prepared analogously to the known compounds or can be synthesised by methods known per se, as described in the literature, e.g. in the standard works such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart, and specifically under reaction conditions which are known and suitable for the specified reactions. In this connection, it is also possible to utilise variants known per se that are not mentioned here in more detail. Furthermore, starting substances can be obtained by generally accessible literature procedures or commercially.
  • the liquid-crystalline medium as used according to the invention is a liquid-crystalline mixture which besides the one or more dichroic dyes further comprises one or more mesogenic compounds.
  • the liquid-crystalline medium as used according to the invention may have a positive dielectric anisotropy or a negative dielectric anisotropy.
  • the absolute value or the magnitude of the dielectric anisotropy of the liquid-crystalline medium preferably is 1.5 or more, more preferably 2.5 or more and in particular 3.0 or more.
  • the dielectric anisotropy As is preferably determined at 20°C and 1 kHz.
  • liquid-crystalline medium having a negative dielectric anisotropy is provided and used in the switchable layer.
  • liquid-crystalline medium having a positive dielectric anisotropy is provided and used in the switchable layer.
  • the liquid-crystalline medium preferably has an optical anisotropy An of 0.06 or more, more preferably 0.08 or more, still more preferably 0.10 or more and even more preferably 0.12 or more.
  • the liquid-crystalline medium preferably has an optical anisotropy An in the range of from 0.03 to 0.30, more preferably from 0.04 to 0.27, even more preferably from 0.06 to 0.21 and in particular from 0.09 to 0.16.
  • liquid-crystalline media preferably exhibit a favourable low temperature stability without visible crystallisation or decomposition, in particular a long shelf life of more than 200 hours measured in bulk at -40°C.
  • the liquid-crystalline medium in particular the liquid-crystalline medium contained in the switchable layer of the electro-optical device, comprises one or more compounds of formula IV-1 in which
  • R 41 and R 42 independently of each other, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C atoms.
  • the one or more compounds of formula IV-1 are contained in the liquid-crystalline medium in a total amount of at least 20% by weight, preferably at least 30% by weight, more preferably at least 40% by weight, even more preferably at least 50% by weight.
  • liquid-crystalline medium comprises one or more compounds selected from the group of compounds of formulae B-1 , B-2 and B-3 in which
  • R 11 and R 12 identically or differently, denote H or a straight-chain alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH2 groups in these radicals are optionally replaced, independently of one h a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen, preferably a straight-chain alkoxy radical having 1 to 7 C atoms.
  • the compounds of formula B-1 are preferably selected from the group of compounds of the formulae B-1-a to B-1-e in which R 11 and R 12 , identically or differently, denote alkyl having 1 to 7 C atoms, preferably ethyl, n-propyl, n-butyl or n-pentyl.
  • the compounds of formula B-2 are preferably selected from the group of compounds of the formulae B-2-a to B-2-e in which R 11 and R 12 , identically or differently, denote alkyl having 1 to 12 C atoms, preferably alkyl having 1 to 7 C atoms.
  • the compounds of formula B-3 are preferably selected from the group of compounds of the formulae B-3-a to B-3-j in which R 12 denotes alkyl having 1 to 7 C atoms, preferably ethyl, n-propyl or n-butyl.
  • the one or more compounds selected from the group of compounds of formulae B-1 , B-2 and B-3 are selected from the group of compounds B- A to B-J
  • the one or more compounds selected from the group of compounds of formulae B-1 , B-2 and B-3, in particular of formula B-2, are preferably comprised in the liquid-crystal medium in a total amount of from 0.5% by weight to 20% by weight, more preferably 4% by weight or more and even more preferably 8% by weight or more.
  • the medium according to the invention comprises one or more compounds of formula Y in which the individual radicals have the following meaning:
  • L 1 , L 2 , L 3 and L 4 independently of each other, denote H, F or Cl, preferably H or F, more preferably F, and x, y independently of each other, denote 0, 1 or 2, with x+y ⁇ 3.
  • the compounds of formula Y contain at least one substituent L 1-4 that is F or Cl, preferably F, more preferably at least two substituents L 1-4 that are F.
  • R 1 and R 2 preferably denote straight-chain alkyl or alkoxy having 1 to 6 C atoms, furthermore alkenyl having 2 to 6 C atoms, in particular vinyl, 1 E-propenyl, 1 E-butenyl, 3-butenyl, 1 E-pentenyl, 3E-pentenyl or 4-pentenyl.
  • both radicals L 1 and L 2 denote F.
  • one of the radicals L 1 and L 2 denotes F and the other denotes Cl.
  • the respective rings, and preferably the phenylene rings optionally may each be substituted by one or two alkyl groups, preferably by methyl and/or ethyl groups, preferably by one methyl group.
  • the medium contains one or more compounds of formula Y that are selected from the following subformulae in which R 1 , R 2 , Z x , Z y , L 1 and L 2 have one of the meanings given in formula Y or one of the preferred meanings as given above and below, a denotes 0, 1 or 2, preferably 1 or 2, b denotes 0, 1 or 2, preferably 1 or 2,
  • L 3 , L 4 independently of each other, denote F or Cl, preferably F.
  • both L 1 and L 2 denote F or one of L 1 and L 2 denotes F and the other denotes Cl
  • both L 3 and L 4 denote F or one of L 3 and L 4 denotes F and the other denotes Cl.
  • the respective rings, and preferably the phenylene rings optionally may each be substituted by one or two alkyl groups, preferably by methyl and/or ethyl groups, preferably by one methyl group.
  • the medium comprises one or more compounds of the formula Y1 selected from the group consisting of the following subformulae in which a denotes 1 or 2, alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, and alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms, and (O) denotes an oxygen atom or a single bond.
  • the medium contains one or more compounds of formula Y1 selected from formulae Y1-2 and Y1-10.
  • the medium comprises one or more compounds of the formulae Y1A-1 to Y1A-10:
  • the medium comprises one or more compounds of the formula Y2 selected from the group consisting of the following subformulae: in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, and alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms, and (O) denotes an oxygen atom or a single bond.
  • the medium contains one or more compounds of formula Y2 selected from formulae Y2-2 and Y2-10, in particular one or more compounds of formula Y2-10.
  • the proportion of the compounds of formula Y1 or its subformulae in the medium is preferably from 1 to 10% by weight.
  • the proportion of the compounds of formula Y2 or its subformulae, in particular formula Y2-10, in the medium is preferably from 1% by weight to 15% by weight, more preferably from 2% by weight to 10% by weight.
  • the total proportion of the compounds of formulae Y1 and Y2 or their subformulae in the medium is preferably from 0 to 20%, very preferably from 1 to 15%, most preferably from 1 to 10% by weight.
  • the medium contains 1, 2 or 3 compounds of formulae Y1 and Y2 or their subformulae, very preferably selected from formulae Y1-2, Y1-10, Y2-2 and Y2-10.
  • the medium comprises one or more compounds of the formulae Y2A-1 to Y2A-5:
  • the medium comprises one or more compounds of formula Y selected from the following subformula in which
  • R 1 , R 2 , L 1 , L 2 , ring X, x and Z x have the meanings given in formula Y, in which at least one of the rings X is cyclohexenylene. If x is 2, preferably, one ring X is cyclohexylene- 1 ,4-diyl and the other ring X is cyclohexylene- 1 ,4-diyl or cyclohexane-1 ,4-diyl.
  • LY x is 1 or 2
  • both radicals L 1 and L 2 denote F.
  • one of the radicals L 1 and L 2 denotes F and the other denotes Cl.
  • the compounds of the formula LY are preferably selected from the group consisting of the following sub-formulae: in which R 1 has the meaning indicated for formula LY above, (O) denotes an oxygen atom or a single bond, and v denotes an integer from 1 to 6.
  • the medium contains 1 , 2 or 3 compounds of formula LY.
  • the proportion of the compounds of formula LY or its subformulae in the medium is preferably from 0 to 15% by weight.
  • the medium contains one or more compounds of formula LY4, wherein the proportion of the compounds of formula LY4 in the medium preferably is from 1 % by weight to 15% by weight, more preferably from 5% by weight to 10% by weight.
  • the medium comprises one or more compounds selected from the group of compounds of formulae Y4-1 to Y4-24 in which R denotes a straight-chain alkyl or alkoxy radical having 1 to 7 C atoms, R* denotes a straight-chain alkenyl radical having 2 to 7 C atoms, (O) denotes an oxygen atom or a single bond, and m denotes an integer from 1 to 6.
  • R preferably denotes methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy or pentoxy.
  • the medium contains one or more compounds of formula Y4-5, preferably in an amount of 0.5% by weight or more, more preferably 1 % by weight or more.
  • the total proportion of the compounds of formula Y, and in particular its respective sub-formulae, in the medium is 5% by weight or more, more preferably 15% by weight or more, and even more preferably 25% by weight or more.
  • the liquid-crystalline medium comprises one or more compounds selected from the group of compounds of formulae 11-1 and 11-2 in which denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C atoms, in which optionally one or more CH2 groups, independently of one are independently of each other
  • L 25 denotes H or CH3
  • X 2 denotes halogen, preferably F, halogenated alkyl or alkoxy with 1 to 3 C atoms or halogenated alkenyl or alkenyloxy with 2 or 3 C atoms.
  • the medium preferably comprises the one or more compounds of formulae 11-1 and/or 11-2 in a total amount of 5% by weight or more, more preferably 10% by weight or more.
  • L 21 and L 22 or L 23 and L 24 are preferably both F.
  • the compounds of formula 11-1 are preferably selected from compounds of formula ll-1-a in which the occurring groups have the meanings given in for formula II- 1 , and wherein preferably X 2 is F.
  • the medium comprises one or more compounds of formula ll-1-a-1 1 , in which R 2 has the meaning as set forth for formula 11-1 .
  • the one or more compounds of formula ll-1-a-1 are preferably contained in the liquid-crystal medium in a total amount of 5% by weight or more, more preferably 10% by weight or more.
  • liquid-crystalline medium comprises one or more compounds selected from the compounds of formulae ll-1-b to 11-1 -h
  • R 2 has the meaning as given in formula 11-1.
  • the compounds of formula 11-2 are preferably selected from the group of compounds of formulae ll-2-a, ll-2-b, ll-2-c and ll-2-d in which the parameters have the respective meanings given for formula 11-2 above, and wherein preferably X 2 is F.
  • the medium comprises compounds of formula ll-2-b, wherein L 21 , L 22 , L 23 and L 24 all are F, preferably in a total amount of 5% by weight or more.
  • the medium comprises one or more compounds selected from the compounds of formula ll-2-d.
  • Especially preferred compounds of formula II-2 are compounds of formulae ll-2-i, ll-2-ii, ll-2-iii and I l-2-iv wherein R 2 has the meaning given for formula 11-2 above.
  • the medium contains at least one compound of formula 11-2- iii, preferably in a total amount of 2.5% by weight or more, more preferably 5% by weight or more.
  • liquid-crystal medium comprises one or more compounds selected from the compounds of formulae II-2-A to II-2-L wherein R 2 has the meaning given for formula 11-2 above.
  • liquid-crystal medium comprises one or more compounds selected from the group of compounds of formulae 111-1 to HI-32 wherein R 3 has the meaning as given for R 2 in formula 11-2 above.
  • the liquid-crystalline medium preferably comprises at least one compound of formula 111-1 , preferably in an amount of at least 2% by weight, more preferably at least 5% by weight.
  • the medium according to the invention comprises one or more compounds of formula IV IV in which
  • R 41 and R 42 independently of each other, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C atoms, preferably R 41 is alkyl with 1 to 7 C atoms and R 42 is alkyl with 1 to 7 C atoms or alkoxy with 1 to 7 C atoms or R 41 is alkenyl with 2 to 7 C atoms and R 42 is alkyl with 1 to 7 C atoms, on each occurrence, identically or differently, denote
  • liquid-crystal media according to the present invention in particular the liquid-crystal media comprised in the switchable layer of the electro-optical device, comprise one or more compounds of formula IV selected from the group of compounds of formulae IV-1 to IV-5
  • R 41 and R 42 have the respective meanings given under formula IV above and in formulae IV-1, IV-4 and IV-5
  • R 41 preferably is alkyl or alkenyl, preferably alkenyl and R 42 preferably is alkyl or alkenyl, preferably alkyl
  • R 41 and R 42 preferably are alkyl and in formula IV-3
  • R 41 preferably is alkyl or alkenyl, preferably alkyl and R 42 preferably is alkyl or alkoxy, preferably alkoxy.
  • the medium according to the invention comprises one or more compounds of formula IV-1 and one or more compounds of formula IV-4.
  • the medium further comprises one or more compounds of formula IV selected from the group of compounds of formulae IV-6 to IV-13
  • R 41 and R 42 independently of each other, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C atoms, and denotes H or F.
  • liquid-crystal medium comprises one or more compounds of formula IV-13, in which L 4 is F.
  • the media may comprise one or more compounds of formula V in which
  • R 5 is alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C atoms, and preferably is alkyl with 1 to 7 C atoms or alkenyl with 2 to 7 C atoms, are, independently of each other,
  • L 51 and L 52 independently of each other, denote H or F, preferably L 51 denotes
  • F, X 5 denotes halogen, halogenated alkyl or alkoxy with 1 to 3 C-atoms or halogenated alkenyl or alkenyloxy with 2 or 3 C-atoms, preferably F, Cl, -OCF 3 or -CF 3 , most preferably F, Cl or -OCF 3
  • the media according to the present invention comprise one or more compounds of formula V selected from the group of compounds of formulae V-1 and V- 2 in which the parameters have the respective meanings given for formula V above, and the parameters L 53 and L 54 are, independently of each other, H or F, and preferably Z 5 is -CH 2 -CH 2 -.
  • the compounds of formula V-1 are selected from the group of compounds of formulae V-1a and V-1b in which the R 5 has the meaning given for formula V above.
  • the compounds of formula V-2 are selected from the group of compounds of formulae V-2a to V-2d in which the R 5 has the meaning given for formula V above.
  • liquid-crystalline media according to the present invention additionally comprise one or more compounds of formula VI in which
  • R 61 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C atoms, preferably R 61 is alkyl having up to 7 C atoms,
  • R 62 denotes F, alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C atoms, or alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C atoms, t on each occurrence, identically or differently, denote
  • the liquid-crystal medium comprises one or more compounds of formula VI- 1 , preferably in a total amount of at least 2.5% by weight, more preferably at least 4% by weight, and in particular at least 7.5% by weight.
  • the medium comprises one or more compounds of formula VI-2, preferably in a total amount of at least 5% by weight, more preferably at least 10% by weight and in particular at least 15% by weight.
  • liquid-crystalline medium comprises the compound of formula which in the following and according to the acronyms explained in Tables A to C is also designated as compound CLP-V-1.
  • the liquid-crystal media according to the invention preferably retain the nematic phase down to -20°C, more preferably down to -30°C, and even more preferably down to -40°C.
  • the liquid-crystal media according to the invention have a clearing point of > 75°C, more preferably > 80°C, and in particular > 85°C.
  • the liquidcrystal media preferably exhibit rotational viscosities yi of ⁇ 110 mPa-s, particularly preferably ⁇ 100 mPa-s, where the rotational viscosities are determined at 20°C.
  • LC displays having fast response times may be favourably provided.
  • the rotational viscosity yi of the liquid-crystal media preferably is ⁇ 80 mPa s, more preferably ⁇ 70 mPa s, and even more preferably ⁇ 60 mPa s.
  • the ratio yi/Kn, in which yi is the rotational viscosity and Ku is the elastic constant for splay deformation, of the liquid-crystal media preferably is ⁇ 4.5 mPa s/pN, more preferably ⁇ 4.2 mPa s/pN, most preferably ⁇ 4.0 mPa s/pN.
  • the nematic phase range of the liquid-crystal media according to the invention preferably has a width of at least 90°C, more preferably of at least 100°C, in particular of at least 110°C. This range particularly preferably extends at least from -25°C to +80°C.
  • liquid-crystal medium can favourably contribute to obtaining an advantageous electro-optical device performance, e.g. in terms of the achievable contrast and the high bright state transmittance, while exhibiting functionality and reliability also at high temperatures and at low temperatures.
  • the electro-optical device preferably comprises a light source.
  • backlighting conventionally used in LC displays may be used for illumination, e.g. LED backlights or cold cathode fluorescent lamp backlights.
  • the polarizers used in the electro-optical device are linear polarizers.
  • a linear polarizer is used to linearly polarize light such that the electric field of light is confined to a single plane along the direction of propagation.
  • a linear polarizer has a transmission axis, also referred to as a polarization axis or polarizing axis, wherein the polarizer is selectively transmissive to light which is linearly polarized parallel to this axis, i.e. aligned along this orientation.
  • the two polarizers as used in the electro-optical device are linear polarizers which are in a crossed configuration, wherein the polarizers are arranged such that the polarization axes are orthogonal with respect to each other.
  • the absorption axis of the one or more dichroic dyes as described herein is parallel to the transmission axis of the second linear polarizer or the absorption axis of the one or more dichroic dyes as described herein and the transmission axis of the second linear polarizer are arranged at an angle of 25° or less.
  • the state of the switchable layer and thus the optical state of the device can be controlled by electrical switching, wherein an electric field may be applied by means of electrodes.
  • the switchable layer can have further switching states, in particular intermediate states, the device preferably is switchable between an optically bright state and an optically dark state, wherein the bright state has a larger degree of light transmission compared to the dark state.
  • the bright state gives maximum light transmission and the dark state gives minimum light transmission.
  • the dark state is provided wherein the absorption axis of the one or more dichroic dyes is parallel or substantially parallel to the transmission axis of the second linear polarizer, especially when the first polarizer and the second polarizer are crossed with respect to each other.
  • the second polarizer is the polarizer which is positioned on the far side from the light source. While optimally the absorption axis and the transmission axis are parallel to each other, in some cases a substantially parallel configuration with some deviation from the parallel alignment may be provided which is still effective and suitable in this embodiment.
  • the absorption axis of the one or more dichroic dyes as described herein and the transmission axis of the second linear polarizer are arranged at an angle, in particular an azimuthal angle, of 25° or less, preferably at an angle of 15° or less, even more preferably at an angle of 5° or less and in particular at an angle close to and around 0°.
  • the liquid-crystalline medium in the dark state has a planar or homogeneous alignment.
  • the light absorption properties are dependent on the orientation of the compounds relative to the direction of polarization of the light.
  • a dichroic dye compound typically has an elongated shape, where the longitudinal or principal molecular axis is significantly longer than the other two spatial dimensions.
  • the absorption axis, and in particular the transition dipole moment is parallel or at least substantially parallel to this longitudinal axis.
  • the absorption axis, and in particular the transition dipole moment is perpendicular or at least substantially perpendicular or transverse to this longitudinal axis.
  • the absorption axis thus defines the orientation or direction within the molecular frame along which light absorption, in particular visible light absorption, occurs.
  • light herein is preferably taken to mean visible light, in particular electromagnetic radiation having wavelengths from 380 nm to 780 nm.
  • the orientation of the one or more dichroic dyes contained in the liquid-crystalline medium and thus the direction or orientation of the absorption axis of the dyes is herein given as a spatial and temporal average.
  • the desired orientation of the dichroic dyes and thus the direction of the absorption axis of the dyes, in particular in the dark state may be provided and controlled by using suitable alignment layers at the cell substrate interfaces and/or suitable electrical control of the switching.
  • the liquid crystal molecules and the dichroic dye molecules in the liquid-crystalline medium contained in the switchable layer are oriented parallel to the substrates and thus exhibit a homogeneous or planar alignment.
  • the absorption axis of the one or more dichroic dyes as described herein and the transmission axis of the second linear polarizer are arranged at an angle in the range of greater than 25° and up to and including 90°.
  • the use of the one or more dichroic dyes according to the invention can still suitably contribute to the beneficial effects in terms of the dark state and the contrast compared to cases where no dyes are included in the switchable layer.
  • the medium may comprise one or more additives, in particular one or more stabilizers, one or more chiral dopants, one or more polymerizable compounds and/or one or more self-alignment additives.
  • alkyl or “alkyl*" herein encompasses straight-chain and branched alkyl groups, preferably having 1-6 carbon atoms, in particular the straight-chain groups methyl, ethyl, propyl, butyl, pentyl and hexyl. Groups having 2-5 carbon atoms are generally preferred.
  • Branched alkyl groups may be selected from secondary and/or tertiary alkyl, preferably from secondary alkyl.
  • alkenyl or “alkenyl*” encompasses straight-chain and branched alkenyl groups, preferably having 2-6 carbon atoms, in particular the straight-chain groups.
  • Preferred alkenyl groups are C2-C?-1 E-alkenyl, C4-Ce-3E-alkenyl, in particular C2-Ce-1 E-alkenyl.
  • alkenyl groups are vinyl, 1 E-propenyl, 1 E-butenyl, 1 E-pentenyl, 1 E-hexenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl and 5-hexenyl.
  • fluoroalkyl preferably encompasses straight-chain groups having a terminal fluorine, i.e. fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl.
  • fluorine i.e. fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl.
  • other positions of the fluorine are not excluded.
  • the liquid-crystal medium additionally comprises one or more polymerisable compounds, for example in view of providing a PS-VA mode device.
  • the liquid-crystalline media according to the present invention comprise one or more polymerisable compounds selected from Table G below.
  • the proportion of polymerisable compounds in the liquid-crystalline medium is from 0.01 to 5%, very preferably from 0.05 to 1%, most preferably from 0.1 to 0.5%.
  • liquid-crystalline medium can lead to advantageous properties like fast response times.
  • a liquid-crystalline medium is especially suitable for use in PSA displays where it shows low image sticking, a quick and complete polymerisation, the quick generation of a low pretilt angle which is stable after UV exposure, a high reliability, high VHR value after UV exposure, and a high birefringence.
  • the polymerisable compounds it is possible to increase the absorption of the liquid-crystalline medium at longer UV wavelengths, so that it is possible to use such longer UV wavelengths for polymerisation, which is advantageous for the display manufacturing process.
  • liquid-crystalline media which have a nematic liquidcrystalline phase, and preferably have no chiral liquid crystal phase.
  • the invention also relates to the use of a liquid-crystalline medium according to the present invention as described above and below for electro-optical purposes, in particular for the use in shutter glasses, for 3D applications, in TN, PS-TN, STN, TN- TFT, OCB, IPS, PS-IPS, FFS, UB-FFS, HB-FFS, PS-FFS, VA and PS-VA displays, and to electro-optical displays, in particular of the aforementioned types, containing a liquid-crystalline medium according to the present invention as described above and below, in particular IPS, FFS, HB-FFS and UB-FFS displays.
  • the electro-optical devices according to the invention are used as or in desktop monitors, notebooks, TVs, mobile telephones, tablet PCs, etc. and multimedia applications.
  • the devices are AR or VR devices, in particular VR displays with very high resolution.
  • the invention also relates to electro-optical displays, such as, for example, STN or MLC displays, having two plane-parallel outer plates, which, together with a frame, form a cell, integrated non-linear elements for switching individual pixels on the outer plates, and a nematic liquid-crystal mixture having negative or respectively positive dielectric anisotropy and high specific resistance located in the cell, wherein the a nematic liquid-crystal mixture is a liquid-crystalline medium according to the present invention as described above and below.
  • electro-optical displays such as, for example, STN or MLC displays, having two plane-parallel outer plates, which, together with a frame, form a cell, integrated non-linear elements for switching individual pixels on the outer plates, and a nematic liquid-crystal mixture having negative or respectively positive dielectric anisotropy and high specific resistance located in the cell, wherein the a nematic liquid-crystal mixture is a liquid-crystalline medium according to the present invention as described above and below
  • liquid-crystalline media according to the invention enable a significant broadening of the available parameter latitude.
  • achievable combinations of clearing point, viscosity at low temperature, thermal and UV stability and suitable optical anisotropy are superior to previous materials from the prior art.
  • VHR voltage holding ratio
  • liquid-crystalline media which can be used in accordance with the invention are prepared in a manner conventional per se, for example by mixing mesogenic compounds and optionally additives.
  • the desired amount of the components used in lesser amount is dissolved in the components making up the principal constituent, advantageously at elevated temperature. It is also possible to mix solutions of the components in an organic solvent, for example in acetone, chloroform or methanol, and to remove the solvent again, for example by distillation, after thorough mixing.
  • the liquid-crystalline media may also comprise further additives known to the person skilled in the art and described in the literature, such as, for example, polymerisation initiators, inhibitors, surface-active substances, stabilizers, antioxidants, e.g. BHT, TEMPOL, microparticles, free-radical scavengers, nanoparticles, etc.
  • polymerisation initiators such as, for example, polymerisation initiators, inhibitors, surface-active substances, stabilizers, antioxidants, e.g. BHT, TEMPOL, microparticles, free-radical scavengers, nanoparticles, etc.
  • stabilizers e.g. BHT, TEMPOL
  • microparticles e.g. TEMPOL
  • free-radical scavengers e.g. TEMPOL
  • nanoparticles e.g., nanoparticles, etc.
  • pleochroic dyes or chiral dopants can be added. Suitable stabilizer
  • the liquid-crystalline media contain one or more chiral dopants, preferably in a concentration from 0.01 to 1% by weight, very preferably from 0.05 to 0.5% by weight.
  • the chiral dopants are preferably selected from the group consisting of compounds from Table E below, very preferably from the group consisting of R- or S- 811, R- or S-1011, R- or S-2011, R- or S-3011, R- or S-4011, and R- or S-5011.
  • liquid-crystalline media contain a racemate of one or more chiral dopants, which are preferably selected from the chiral dopants mentioned in the previous paragraph.
  • the LC medium according to the present invention contains a self-aligning or self-alignment (SA) additive, preferably in a concentration of 0.1 to 2.5% by weight.
  • SA self-aligning or self-alignment
  • An LC medium according to this embodiment is especially suitable for use in polymer stabilised SA-FFS, SA-UB-FFS or SA-HB-FFS displays.
  • SA-FFS, SA-UB-FFS or SA-HB-FFS display according to the present invention does not contain a polyimide alignment layer.
  • the SA-FFS, SA-UB-FFS or SA-HB-FFS display contains a polyimide alignment layer.
  • Preferred SA additives for use in this embodiment are selected from compounds comprising a mesogenic group and a straight-chain or branched alkyl side chain that is terminated with one or more polar anchor groups selected from hydroxy, carboxy, amino or thiol groups.
  • SA additives contain one or more polymerisable groups which are attached, optionally via spacer groups, to the mesogenic group.
  • These polymerisable SA additives can be polymerised in the LC medium under similar conditions as applied for the RMs in the PSA process.
  • Suitable SA additives to induce homeotropic alignment are described for example in US 2013/0182202 A1, US 2014/0838581 A1, US 2015/0166890 A1 and US 2015/0252265 A1.
  • an LC medium or a polymer stabilised SA-FFS, SA- UB-FFS or SA-HB-FFS display according to the present invention contains one or more self-aligning additives selected from Table H below.
  • liquid-crystalline media for example, 0 to 15% by weight of nanoparticles, conductive salts, preferably ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (cf. , for example, Haller et al., Mol. Cryst. Liq. Cryst. 24, 249-258 (1973)), for improving the conductivity, or substances for modifying the dielectric anisotropy, the viscosity and/or the alignment of the nematic phases. Substances of this type are described, for example, in DE-A 22 09 127, 22 40 864, 2321 632, 23 38 281, 24 50 088, 26 37430 and 28 53 728.
  • conductive salts preferably ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutylammonium tetraphen
  • the displays according to the present invention are preferably addressed by an active matrix, preferably by a matrix of TFT.
  • the liquid crystals according to the invention can also advantageously be used in displays having other known addressing means.
  • the structures of the mesogenic compounds are indicated by means of abbreviations, also referred to as acronyms.
  • the chemical formulae are abbreviated as follows using Tables A to C below. All groups CnH2n+1. CmH2m+1 and C1H21+1 or CnH2n-1.
  • CmH2m-1 and C1H21-1 denote straight-chain alkyl or alkenyl, preferably 1E-alkenyl, having n, m and I C atoms respectively, where n, m and I, independently of one another, denote an integer from 1 to 9, preferably 1 to 7, or from 2 to 9, preferably 2 to 7, respectively.
  • C0H20+I denotes straight-chain alkyl having 1 to 7, preferably 1 to 4, C atoms, or branched alkyl having 1 to 7, preferably 1 to 4, C atoms.
  • Table A lists the codes used for the ring elements of the core structures of the compounds, while Table B shows the linking groups.
  • Table C gives the meanings of the codes for the left-hand or right-hand end groups.
  • Table D shows illustrative structures of compounds with their respective abbreviations.
  • n and m each denote integers, and the three dots are placeholders for other abbreviations from this table.
  • the illustrative structures show compounds which are particularly preferably employed. in which k, I, m and n are, independently of one another, each an integer, preferably from 1 to 9, more preferably from 1 to 7.
  • Table E indicates possible chiral dopants which are optionally added to the liquidcrystal media according to the invention.
  • the liquid-crystal media preferably comprise 0-10% by weight, in particular 0.01-5% by weight and particularly preferably 0.01-3% by weight of chiral dopants.
  • Stabilizers which may preferably be added to the liquid-crystal media in amounts of 0.005-3% by weight are shown below.
  • Table G shows illustrative reactive mesogenic compounds (RMs) which can be used in the liquid-crystal media in accordance with the present invention.
  • the liquid-crystalline media according to the invention comprise one or more polymerisable compounds, preferably selected from the polymerisable compounds of the formulae RM-1 to RM-145.
  • polymerisable compounds preferably selected from the polymerisable compounds of the formulae RM-1 to RM-145.
  • 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-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM- 117, RM-120, RM-121 and RM-122 are particularly preferred.
  • Table H shows self-alignment additives for vertical alignment which can be used in LC media for SA-VA and SA-FFS displays according to the present invention, optionally together with the polymerisable compounds.
  • the LC media comprise one or more SA additives selected from formulae SA-1 to SA-34, preferably from formulae SA-14 to SA-34, more preferably from formulae SA-20 to SA-28, most preferably of formula SA-20, in particular in combination with one or more RMs.
  • parts or per cent data denote parts by weight or per cent by weight based on the mixture as a whole.
  • V10 voltage [V] for 10% transmission n e extraordinary refractive index measured at 20°C and 589 nm, n 0 ordinary refractive index measured at 20°C and 589 nm, An optical anisotropy measured at 20°C and 589 nm, e ⁇ dielectric susceptibility (or "dielectric constant") perpendicular to the longitudinal axes of the molecules at 20°C and 1 kHz, s H dielectric susceptibility (or “dielectric constant”) parallel to the longitudinal axes of the molecules at 20°C and 1 kHz,
  • threshold voltage for the present invention relates to the capacitive threshold (V o ), unless explicitly indicated otherwise.
  • the optical threshold can also be indicated, for example for 10% relative contrast (V10).
  • the nematic host mixtures H1 to H13 are prepared as follows.
  • compound B-2-b corresponds to the compound of formula B-2-b as specified and shown in the description above, wherein R 12 is ethyl.
  • compound B-2-b 4.00% clearing point [°C]: 90.5
  • the dye mixture DM1 as shown above is added to mixture M1 in the respective amounts as shown in the following Table to respectively obtain mixtures M1.1 , M1.2, M1.3, M1.4, M1.5 and M1.6 and comparative mixtures CM 1.1 and CM 1.2.
  • the mixtures M1.1 to M 1.6 have same or very similar values of the optical anisotropy, dielectric anisotropy, elastic constants and rotational viscosity.
  • the optical anisotropy is altered appreciably.
  • the mixtures M1.1 , M1.2, M1.3, M1.4, M1.5 and M1.6 and the comparative mixtures CM 1.1 and CM 1.2 are respectively filled in FFS electro-optical cells and their electro- optical performance is evaluated.
  • the cell containing comparative mixture CM 1.2 shows less favourable operating voltage and response time.
  • the cell containing comparative mixture CM 1.2 shows a significantly decreased transmittance in the bright state.
  • the cells containing the mixtures M1.1 to M 1.6 exhibit favourable bright state transmittance, favourable contrast ratios and favourable response times.
  • mixture M2 0.040% of the compound ST-1 shown above and 0.005% of the compound of the formula which in the following will be referred to as ST-2, are added to obtain mixture M2.
  • the dye mixture DM1 as shown above is added to mixture M2 in the respective amounts as shown in the following Table to respectively obtain mixtures M2.1, M2.2, M2.3, M2.4, M2.5 and M2.6 and comparative mixtures CM2.1 and CM2.2.
  • the mixtures M2.1 to M2.6 have same or very similar values of the optical anisotropy, dielectric anisotropy, elastic constants and rotational viscosity.
  • the optical anisotropy is altered appreciably.
  • the mixtures M2.1, M2.2, M2.3, M2.4, M2.5 and M2.6 and the comparative mixtures CM2.1 and CM2.2 are respectively filled in FFS cells and their electro-optical performance is evaluated. Compared to the cells respectively containing the mixtures M2.1 to M2.6 and comparative mixture CM2.1 , the cell containing comparative mixture CM2.2 shows less favourable operating voltage and response time.
  • the cell containing comparative mixture CM2.2 shows a significantly decreased transmittance in the bright state.
  • the cells containing the mixtures M2.1 to M2.6 exhibit favourable bright state transmittance, favourable contrast ratios and favourable response times.
  • Mixtures M3.1, M3.2, M3.3, M3.4, M3.5 and M3.6 and comparative mixtures CM3.1 and CM3.2 are prepared analogous to mixtures M2.1, M2.2, M2.3, M2.4, M2.5 and M2.6 and comparative mixtures CM2.1 and CM2.2 as described above, wherein instead of reference mixture H2 the reference mixture H3 shown above is used.
  • the mixtures M3.1, M3.2, M3.3, M3.4, M3.5 and M3.6 give favourable device performance, in particular favourable contrast, transmittance and response times in displays.
  • Mixture M4 is obtained by adding to mixture B4 0.16% of Dye-1 shown above, 0.35% of Dye-2 shown above and 0.43% of Dye-3 shown above.
  • the mixture M4 gives a favourable device performance, in particular favourable contrast, transmittance and response times in displays.
  • Mixture M5 is obtained by adding to mixture B5 0.047% of Dye-1 shown above, 0.092% of Dye-2 shown above and 0.110% of Dye-3 shown above.
  • the mixture M5 gives a favourable device performance, in particular favourable contrast, transmittance and response times in displays.
  • the mixture M6 gives a favourable device performance, in particular favourable contrast, transmittance and response times in displays.
  • a dichroic dye mixture DM2 is provided containing 9% of Dye-4, 20% of Dye-5, 17% of Dye-6, 26% of Dye-7 and 28% of Dye-8.
  • mixture M7 To mixture M1 shown above 0.2% of the dye mixture DM2 is added to obtain mixture M7.
  • the mixture M1 which contains no dye is filled in an electro-optical cell (ITO-coated glass susbtrates with polyimide alignment layers), wherein the cell further includes a first linear polarizer facing the light source and a second linear polarizer which faces away from the light source and which is oriented perpendicular to the first linear polarizer.
  • the visible light transmission in the dark state is measured, where residual light leakage is observed.
  • Example 7.1 the mixture M7 is filled in an electro-optical cell with crossed linear polarizers, wherein in the dark state the absorption axis of the dichroic dyes is parallel to the transmission axis of the first linear polarizer which is facing the light source.
  • the visible light transmission in the dark state is measured.
  • the light leakage in the dark state is decreased and the transmission is only 81% relative to the dark state transmission of the cell in Comparative Example 7.
  • Example 7.2 the mixture M7 is filled in an electro-optical cell with crossed linear polarizers, wherein in the dark state the absorption axis of the dichroic dyes is parallel to the transmission axis of the second linear polarizer which is facing away from the light source, i.e. parallel to the polarizer which is positioned on the far side from the light source.
  • the visible light transmission in the dark state is measured.
  • the light leakage in the dark state is decreased even further and the transmission is only 74% relative to the dark state transmission of Comparative Example 7.
  • mixture M8 To mixture M2 shown above 0.2% of the dye mixture DM2 is added to obtain mixture M8.
  • the mixture M2 which contains no dye is filled in an electro-optical cell with crossed polarizers.
  • the visible light transmission in the dark state is measured, where residual light leakage is observed.
  • Example 8.1 the mixture M8 is filled in an electro-optical cell with crossed polarizers, wherein in the dark state the absorption axis of the dichroic dyes is parallel to the transmission axis of the first linear polarizer which is facing the light source.
  • the visible light transmission in the dark state is measured.
  • the light leakage in the dark state is decreased and the transmission is only 76% relative to the dark state transmission of Comparative Example 8.
  • the mixture M8 is filled in an electro-optical cell with crossed polarizers, wherein in the dark state the absorption axis of the dichroic dyes is parallel to the transmission axis of the second linear polarizer which is facing away from the light source.
  • the visible light transmission in the dark state is measured.
  • the light leakage in the dark state is decreased even further and the transmission is only 70% relative to the dark state transmission of Comparative Example 8.
  • mixture M9 0.2% of the dye mixture DM2 is added to obtain mixture M9.
  • the mixture B9 which contains no dye is filled in an electro-optical cell with crossed polarizers. The visible light transmission in the dark state is measured, where residual light leakage is observed.
  • Example 9.1 the mixture M9 is filled in an electro-optical cell with crossed polarizers, wherein in the dark state the absorption axis of the dichroic dyes is parallel to the transmission axis of the first linear polarizer which is facing the light source.
  • the visible light transmission in the dark state is measured.
  • the light leakage in the dark state is decreased and the transmission is only 80% relative to the dark state transmission of Comparative Example 9.
  • Example 9.2 the mixture M9 is filled in an electro-optical cell with crossed polarizers, wherein in the dark state the absorption axis of the dichroic dyes is parallel to the transmission axis of the second linear polarizer which is facing away from the light source.
  • the visible light transmission in the dark state is measured.
  • the light leakage in the dark state is decreased even further and the transmission is only 72% relative to the dark state transmission of Comparative Example 9.
  • mixture M10 0.10% of the dye mixture DM2 is added to obtain mixture M10.
  • the mixture B10 which contains no dye is filled in an electro-optical cell with crossed polarizers.
  • the visible light transmission in the dark state is measured, where residual light leakage is observed.
  • the mixture M10 is filled in an electro-optical cell with crossed polarizers, wherein in the dark state the absorption axis of the dichroic dyes is parallel to the transmission axis of the first linear polarizer which is facing the light source.
  • the visible light transmission in the dark state is measured.
  • the light leakage in the dark state is decreased and the transmission is only 97% relative to the dark state transmission of Comparative Example 10.
  • the mixture M10 is filled in an electro-optical cell with crossed polarizers, wherein in the dark state the absorption axis of the dichroic dyes is parallel to the transmission axis of the second linear polarizer which is facing away from the light source.
  • the visible light transmission in the dark state is measured.
  • the light leakage in the dark state is decreased even further and the transmission is only 79% relative to the dark state transmission of Comparative Example 10.
  • M12 is treated analogous to mixture M1 as described above.
  • mixture M13 0.050% of the compound ST-1 shown above and 0.015% of the compound of the formula which in the following will be referred to as ST-4, are added to obtain mixture M13.
  • Example 13 Mixture M14 is prepared by including 0.25% of Dye-5, 0.50% of Dye-6 and 0.25% of Dye-7 in reference mixture H1 shown above.
  • the mixture M14 gives a favourable device performance, in particular favourable contrast, transmittance and response times in displays.
  • Mixture M15 is prepared by including 1.00% of Dye-6 and 1.00% of Dye-7 in reference mixture H1 shown above.
  • the mixture M15 gives a favourable device performance, in particular favourable contrast, transmittance and response times in displays.

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Abstract

La présente invention concerne des dispositifs électro-optiques et en particulier des dispositifs d'affichage à cristaux liquides à rendement énergétique élevé comprenant une couche commutable à cristaux liquides contenant un ou plusieurs colorants dichroïques dans des quantités relativement petites, des milieux de cristaux liquides destinés à être utilisés dans lesdits dispositifs, et l'utilisation desdits colorants dichroïques dans des affichages à cristaux liquides pour réduire les fuites de lumière et améliorer le rapport de contraste.
PCT/EP2022/082871 2021-11-24 2022-11-22 Milieu de cristaux liquides et dispositif d'affichage à cristaux liquides WO2023094404A1 (fr)

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DE3126108A1 (de) 1981-07-02 1983-01-20 Merck Patent Gmbh, 6100 Darmstadt "fluessigkristallines dielektrikum, neue dichroitische naphthochinonfarbstoffe und elektrooptisches anzeigeelement"
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