WO2025190813A1 - Milieu à cristaux liquides - Google Patents

Milieu à cristaux liquides

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Publication number
WO2025190813A1
WO2025190813A1 PCT/EP2025/056317 EP2025056317W WO2025190813A1 WO 2025190813 A1 WO2025190813 A1 WO 2025190813A1 EP 2025056317 W EP2025056317 W EP 2025056317W WO 2025190813 A1 WO2025190813 A1 WO 2025190813A1
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atoms
compounds
denotes
formula
alkyl
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Inventor
Sven Christian Laut
Hee-Kyu Lee
Minghui Yang
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Merck Patent GmbH
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Merck Patent GmbH
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • 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
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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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
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    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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    • C09K2019/0444—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
    • C09K2019/0448—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 end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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    • C09K2019/0444—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
    • C09K2019/0455—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 -CF2CF2-, -CF2CF2CF2CF2- or -CH2CF2CF2CH2- chain
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3004—Cy-Cy
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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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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/301—Cy-Cy-Ph
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3016—Cy-Ph-Ph
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • 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
    • C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
    • C09K2019/3037—Cy-Cy-C2H4-Ph
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • 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
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • C09K2019/3071—Cy-Cy-COO-Cy

Definitions

  • the present invention relates to liquid-crystal (LC) media having negative dielectric anisotropy and to the use thereof for optical, electro-optical and electronic purposes, in particular in LC displays.
  • LC liquid-crystal
  • LCD liquid-crystal display
  • TN twisted nematic
  • 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 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, non-linear 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, as known from the prior art.
  • TFTs thin-film transistors
  • FFS displays have been disclosed (see 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 shows a more favorable 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 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.
  • 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.
  • VA displays of the more recent type uniform alignment of the LC molecules is restricted to a plurality of relatively small domains within the LC cell. Disclinations may exist between these domains, also known as tilt domains.
  • VA displays having tilt domains have, compared with conventional VA displays, a greater viewing-angle independence of the contrast and the grey shades.
  • displays of this type are simpler to produce since additional treatment of the electrode surface for uniform alignment of the molecules in the switched-on state, such as, for example, by rubbing, is no longer necessary. Instead, the preferential direction of the tilt or pretilt angle is controlled by a special design of the electrodes.
  • MVA multidomain vertical alignment
  • the slitted electrodes generate an inhomogeneous electric field in the LC cell on application of a voltage, meaning that controlled switching is still achieved.
  • the separations between the slits and protrusions can be increased, but this in turn results in a lengthening of the response times.
  • PVA patterned VA
  • protrusions are rendered completely superfluous in that both electrodes are structured by means of slits on the opposite sides, which results in increased contrast and improved transparency to light but is technologically difficult and makes the display more sensitive to mechanical influences (“tapping”, etc.).
  • a shortening of the response times and an improvement in the contrast and luminance (transmission) of the display are demanded.
  • PS polymer sustained
  • PSA polymer sustained alignment
  • a small amount for example 0.3% by weight, typically ⁇ 1% by weight
  • the polymerisation is carried out at a temperature where the LC medium exhibits a liquid crystal phase, usually at room temperature.
  • RMs reactive mesogens
  • PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS and PS-TN displays are known.
  • the polymerisation of the RMs preferably takes place with an applied voltage in the case of PS-VA and PS-OCB displays, and with or without, preferably without, an applied voltage in the case of PS-IPS displays.
  • the PS(A) method results in a pretilt in the cell. In the case of PS-VA displays, the pretilt has a positive effect on response times.
  • a standard MVA or PVA pixel and electrode layout can be used.
  • PS-VA displays are described, for example, in EP 1 170 626 A2, US 6,861 ,107, US 7,169,449, US 2004/0191428 A1, US 2006/0066793 A1 , and US 2006/0103804 A1.
  • the PSA method can provide significant advantages here.
  • a shortening of the response times, which correlate with a measurable pretilt in test cells, can be achieved without significant adverse effects on other parameters.
  • LC media for use in PSA displays do often exhibit high viscosities and, as a consequence, high switching times.
  • LC media containing alkenyl compounds often show a decrease of the reliability and stability, and a decrease of the VHR especially after exposure to UV radiation.
  • the photo-polymerisation of the RMs in the PSA display is usually carried out by exposure to UV radiation, which may cause a VHR drop in the LC medium.
  • media with negative dielectric anisotropy have an intrinsic disadvantage compared to LC media with positive dielectric anisotropy.
  • mixtures with negative dielectric anisotropy enable a higher transmittance in standard FFS cell layouts and therefore its use has a positive impact on the power consumption and the environment.
  • displays with high transmission which enable the use of less intensive backlight, which, therefore, leads to longer battery lifetime, hence, more sustainable products.
  • displays with higher brightness can be achieved having improved contrast especially under ambient light.
  • the popularity of 8K and gaming monitors leads to an increased need for LC display panels having higher refresh rates and thus for LC media having faster response times.
  • the contrast ratio is described by the ratio between the bright and the dark state of the display which relates to the transmittance (white level) and the scattering parameter (dark level).
  • the dark state is strongly impacted by scattering which has therefore a big impact on the contrast ratio.
  • To improve the contrast ratio and to reduce the scattering LC mixtures with very low birefringence and high elastic constants are necessary while keeping a fast response time.
  • current LC singles and LC mixtures are limited in achieving extremely high elastic constants especially when a low birefringence is required. Therefore, new materials need to be found to increase the contrast ratio of future displays even further.
  • the invention is based on the object of providing novel suitable LC media, which do not have the disadvantages indicated above or do so to a reduced extent.
  • liquid crystalline media with a suitably high negative dielectric anisotropy (As), a suitable phase range and birefringence (An) and high LTS can be realized which do not exhibit the drawbacks of the materials of the prior art or at least do exhibit them to a significantly lesser degree by using liquid crystalline media according to claim 1 .
  • the invention relates to a liquid crystal medium comprising a) one or more compounds of formula I
  • R 11 and R 12 identically or differently, denote H, straight chain alkyl or alkoxy each having 1 to 15 C atoms, straight chain alkenyl or alkenyloxy each having 2 to 15 C atoms or branched alkyl, alkoxy, alkenyl, or alkenyloxy each having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, -OCF 2 -, -O-, -CO-O- or -O-CO- in such 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,
  • L 11 and L 12 independently denote F or Cl, preferably F,
  • Y 1 denotes H or methyl, preferably H
  • R21A R21 B R21C R21 D R22A R22B R22C and R 22D identically or differently, denote H, a straight chain alkyl or alkoxy radical having 1 to 15 C atoms, or a branched alkyl or alkoxy radical having 3 to 15 C atoms, where one or more CH2 groups in these radicals may each be replaced,
  • L 21 and L 22 each, independently of one another, denote F, Cl, CF3 or CHF2,
  • Y 2 denotes H, F, Cl, CF 3 , CHF 2 or CH 3 ,
  • the invention furthermore relates to an LC display comprising an LC medium according to the invention, in particular a VA, IPS, FFS or LIB-FFS or PSA display, particularly preferably an FFS, LIB-FFS, VA or a PS-VA display.
  • an LC display comprising an LC medium according to the invention, in particular a VA, IPS, FFS or LIB-FFS or PSA display, particularly preferably an FFS, LIB-FFS, VA or a PS-VA display.
  • the invention furthermore relates to the use of the LC media according to the invention in PSA displays, in particular to the use in PSA displays containing an LC medium, to produce a tilt angle in the LC medium by in-situ polymerisation of polymerisable reactive mesogens (RM) in the PSA display, preferably in an electric or magnetic field.
  • RM polymerisable reactive mesogens
  • the invention furthermore relates to a process for preparing an LC medium as described above and below, comprising the steps of mixing one or more compounds of the formula I with one or more compounds of the formulae HA, 11 B, IIC and/or HD, and optionally with one or more chiral dopants, and optionally with one or more polymerisable compounds and optionally with further LC compounds and/or additives.
  • the invention furthermore relates to the use of LC media according to the invention in polymer stabilised SA-VA displays, and to a polymer stabilised SA-VA display comprising the LC medium according to the invention.
  • the invention furthermore relates to a process for manufacturing an LC display as described above and below, comprising the steps of filling, or otherwise providing an LC medium, which optionally comprises one or more polymerisable compounds as described above and below, between the substrates of the display, and optionally polymerising the polymerisable compounds.
  • the LC media according to the invention show the following advantageous properties, in particular when used in FFS displays:
  • the compounds of the formula I are selected from the compounds of the formulae 1-1 to 1-12, very preferably of the formula 1-1 in which R 11 , R 12 and Y 1 have the meanings defined above and preferably
  • R 11 denotes straight chain alkyl having 1 to 15 C atoms or branched alkyl having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one another, more preferably straight chain alkyl having
  • R 12 denotes straight chain alkoxy having 1 to 15 C atoms or branched alkoxy having 3 to
  • the medium according to the invention comprises one or more compounds of the formula 1-1 , more preferably selected from the compounds of the formulae 1-1-1 to
  • R 12 denotes straight chain alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, or cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopentylmethyl, 2- fluoroethyl, or 3-fluoropropyl.
  • the compounds of the general formula I are prepared by methods known per se, as described in the literature (for example in the standard works, such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme- Verlag, Stuttgart), to be precise under reaction conditions which are known and are suitable for said reactions. Use can be made here of variants which are known per se but are not mentioned here in greater detail.
  • the starting materials can also be formed in situ by not isolating them from the reaction mixture, but instead by immediately reacting them further into the compounds of the general formula I.
  • Preferred compounds of the formulae HA, IIB and IIC are indicated below: in which the parameter a denotes 1 or 2, alkyl and alkyl* each, independently of one another, denote a straight-chain or branched or cyclic alkyl radical having 1-12 C atoms, and alkenyl and alkenyl* each, independently of one another, denote a straight-chain or branched alkenyl radical having 2-12 C atoms, and (O) denotes an oxygen atom or a single bond.
  • the medium according to the invention comprises one or more compounds of the formula HD selected from the group of compounds of the formulae IID-1 , IID-2 and IID-3 in which R 21D , R 22D , L 21 , L 22 , and Y 2 have the meanings given above and preferably R 21 D denotes straight chain alkyl having 1 to 15 C atoms or branched alkyl having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, ably straight chain alkyl having 2 to 7 C atoms,
  • R 22D denotes straight chain alkoxy having 1 to 15 C atoms or branched alkoxy having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, ably straight chain alkoxy having 1 to 7 C atoms.
  • the compounds of the formula IID-1 to IID-3 are preferably selected from the following sub-formulae: in which R 21D and R 22D have the meanings defined above.
  • the medium comprises one or more compounds of formula
  • R 22D denotes (CH 2 ) S j n which r is 0, 1 , 2, 3, 4, 5 or 6 and s is 1 , 2 or 3.
  • Preferred compounds of formula 11 D-2a are the compounds 11 D-2a-1 to 11 D-2a-14.
  • Particularly preferred mixtures according to the 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-1 , and IID-2.
  • Preferred media according to the invention comprise at least one compound of the formula IIC-1, in which alkyl and alkyl* have the meanings indicated above.
  • the medium comprises one or more compounds of the formula IIA-2 selected from the following sub-formulae:
  • the medium comprises one or more compounds of the formulae I IA-2a-1 to IIA-2a-5:
  • the medium comprises one or more compounds of the formula IIA-10 selected from the following sub-formulae:
  • the medium comprises one or more compounds of the formula I IB-10 selected from the following sub-formulae:
  • the medium comprises one or more compounds of the formulae I IB-10a-1 to I IB-1 Oa-5:
  • the medium comprises one or more compounds of the formulae I IC-1 a-1 and I IC-1 a-2 in which alkyl denotes straight chain alkyl having 1 to 7 C atoms, preferably 2 to 5 C atoms, very preferably denotes ethyl.
  • the medium according to the invention preferably comprises one or more compounds of formula III in which
  • R 31 and R 32 each, independently of one another, denote H, an alkyl or alkoxy radical having 1 to 15 C atoms, where one or more CH2 groups in these radicals may each be
  • L 31 and L 32 each, independently of one another, denote F, Cl, CF 3 or CHF 2 , preferably H or F, most preferably F, and W denotes O or S.
  • the compounds of formula III are preferably selected from the compounds of the formula 111-1 and/or HI-2 in which the occurring groups have the same meanings as given under formula III above and preferably
  • R 31 and R 32 each, independently of one another, an alkyl, alkenyl or alkoxy radical having up to 15 C atoms, more preferably one or both of them denote an alkoxy radical and L 31 and L 32 each preferably denote F.
  • the compounds of the formula 111-1 are selected from the group of compounds of the formulae 111-1-1 to 111-1-11 , preferably of formula 111-1-6, alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, alkenyl, and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms, alkoxy and alkoxy* each, independently of one another, denote a straight-chain alkoxy radical having 1-6 C atoms, and L 31 and L 32 each, independently of one another, denote F or Cl, preferably both F.
  • the compounds of the formula III-2 are selected from the group of compounds of the formulae II 1-2-1 to 111-2-10, preferably of formula III-2-6, in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, alkenyl, and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms, alkoxy and alkoxy* each, independently of one another, denote a straight-chain alkoxy radical having 1-6 C atoms, and L 31 and L 32 each, independently of one another, denote F or Cl, preferably both F.
  • the medium comprises one or more compounds of the formula IIIA-1 and/or
  • R IIIA denotes alkyl or alkenyl having up to 7 C atoms or a group Cy-C m H2m+i-, m and n are, identically or differently, 0, 1 , 2, 3, 4, 5 or 6, preferably 1 , 2 or 3, very preferably 1 ,
  • Cy denotes a cycloaliphatic group having 3, 4 or 5 ring atoms, which is optionally substituted with alkyl or alkenyl each having up to 3 C atoms, or with halogen or CN, and preferably denotes cyclopropyl, cyclobutyl, cyclopentyl, cyclopent- 1-enyl, cyclopent-2-enyl and cyclopent-3-enyl.
  • the compounds of formula IIIA-1 and/or IIIA-2 are contained in the medium either alternatively or in addition to the compounds of formula III, preferably additionally.
  • IIIA-1 and IIIA-2 are the following: IIIA-2-4 alkoxy
  • alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms or alternatively - (CH2) n F in which n is 2,3,4, or 5, preferably C2H4F.
  • the medium comprises one or more compounds of formula HI-3 in which
  • the compounds of formula HI-3 are preferably selected from the group of compounds of the formulae HI-3-1 to HI-3-10:
  • R 32 denotes alkyl having 1 to 7 C-atoms, preferably ethyl, n-propyl or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl or alternatively - (CH2) n F in which n is 2,3,4, or 5, preferably C2H4F.
  • the medium comprises one or more compounds of the formulae HI-4 to HI-6, preferably of formula 111-5, in which the parameters have the meanings given above, R 31 preferably denotes straight- chain alkyl and R 32 preferably denotes alkoxy, each having 1 to 7 C atoms.
  • the medium comprises one or more compounds of the formula HI selected from the group of compounds of formulae HI-7 to HI-9, preferably of formula III- 8, in which the parameters have the meanings given above, R 31 preferably denotes straight- chain alkyl and R 32 preferably denotes alkoxy each having 1 to 7 C atoms.
  • the medium comprises one or more compounds of the formula IV, in which
  • R 41 denotes an alkyl radical having 1 to 7 C atoms or an alkenyl radical having 2 to 7 C atoms, preferably an n-alkyl radical, particularly preferably having 2, 3, 4 or 5 C atoms, and
  • R 42 denotes an alkyl radical having 1 to 7 C atoms or an alkoxy radical having 1 to 6 C atoms, both preferably having 2 to 5 C atoms, an alkenyl radical having 2 to 7 C atoms, preferably having 2, 3 or 4 C atoms, more preferably a vinyl radical or a 1 -propenyl radical and in particular a vinyl radical.
  • the compounds of the formula IV are preferably selected from the group of the compounds of the formulae I V-1 to I V-4, in which alkyl and alkyl’, independently of one another, denote alkyl having 1 to 7 C atoms, preferably having 1 to 5 C atoms, alkenyl denotes an alkenyl radical having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably 2 C atoms, alkenyl’ denotes an alkenyl radical having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably having 2 to 3 C atoms, and alkoxy denotes alkoxy having 1 to 5 C atoms, preferably having 2 to 4 C atoms.
  • the compounds of the formula IV- 1 are preferably selected from the group of compounds of the formulae IV-1-1 to IV-1-6
  • the compounds of the formula IV-2 are preferably selected from the compounds of the formulae I V-2-1 and IV-2-2
  • the compounds of the formula IV-3 are preferably selected from the group of the compounds of the formulae IV-3-1, IV-3-2 and IV-3-3: IV-3-1 in which alkyl has the meanings defined above.
  • the compounds of the formula IV-3-1 , IV-3-2 and IV-3-3 are preferably selected from the following compounds:
  • the medium according to the invention comprises a compound of formula
  • liquid-crystalline medium preferably additionally comprises one or more compounds of the formula IVa, in which
  • R 41 and R 42 each, independently of one another, denote a straight-chain alkyl, alkoxy, alkenyl, alkoxyalkyl or alkoxy radical having up to 12 C atoms, and
  • Preferred compounds of the formula IVa are indicated below: in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1 to 6 C atoms.
  • the medium according to the invention preferably comprises at least one compound of the formula IVa-1 and/or formula IVa-2.
  • the medium comprises one or more compounds of formula IVb-1 to IVb-4, more preferably of the compounds of the formulae IVb-1 to IVb-3 in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1 to 6 C atoms, and alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2 to 6 C atoms.
  • the compounds of the formula IVb-2 are particularly preferred.
  • biphenyls are in which alkyl* denotes an alkyl radical having 1 to 6 C atoms and preferably denotes n- propyl.
  • the medium according to the invention particularly preferably comprises one or more compounds of the formulae IVb-1-1 and/or IVb-2-3.
  • the medium according to the invention comprises one or more compounds of formula V
  • R 51 , R 52 denote alkyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms, or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms,
  • the compounds of formula V are preferably selected from the compounds of the formulae in which the groups occurring have the meanings given above for formula V.
  • the compounds of formula V-1 are preferably selected from the compounds of the formulae V-1-1 to V-1-8; the compounds of formula V-2 are preferably selected from the compounds of the formulae V-2-1 to V-2-4; and the compounds of formula V-3 are preferably selected from the compounds of the formulae V-3-1 to V-3-4: in which R 51 and R 52 have the meanings indicated for formula V above.
  • R 51 and R 52 preferably each, independently of one another, denote straight-chain alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms.
  • Very preferred compounds of the formula V-2-1 are selected from the compounds of the formulae V-2-1 a to V-2-1 g
  • the medium according to the invention comprises one or more compounds of the formula V-3-5 in which R 51 and R 52 identically or differently, denote H, straight chain alkyl or alkoxy having 1 to 15
  • L 51 and L 52 denotes H
  • the other one of L 51 and L 52 denotes H, F, Cl, CF3 or CHF2, preferably H or F, very preferably H.
  • the compounds of the formula V-3-5 are preferably selected from the compounds of the formulae V-3-5- 1 to V-3-5-3 in which R 51 and R 52 have the meanings defined above for formula V-3-5 and preferably denote straight chain alkyl having 1 to 7 C atoms, or straight chain alkenyl having 2 to 15 C atoms where one or more CH2 groups in these radicals may each be replaced,
  • the medium according to the invention comprises one or more compounds of the formula CL in which
  • R L denotes H, a straight chain or branched alkyl or alkoxy radical having 1 to 15 C atoms, or a straight chain or branched alkenyl radical having 2 to 15 C atoms, where one or more CH2 groups in these radicals may each be replaced, independently of one another,
  • X L denotes F, Cl, CN, CHF2, CF3, OCF3, or, identically or differently, has one of the meanings of R L ,
  • Y L denotes H, F, Cl or CH3.
  • the compounds of formula CL are preferably selected form the group of compounds of the formulae CL-1, CL-2 and CL-3: in which
  • R L1 and R L2 identically or differently, have the meanings given above for formula I and, preferably denote alkyl or alkenyl having 1 to 7 C atoms or 2 to 7 C atoms, respectively, in which a CH2 group may be replaced by cyclopropane- 1, 2-diyl, and R L2 alternatively denotes alkoxy having 1 to 5 C atoms.
  • Very preferred compounds of the formula CL are selected from the compounds of the formulae CL-3-1 to CL-3-12:
  • the medium according to the invention comprises the compound CL-3-1 or CLP-3-3.
  • the medium additionally comprises one or more compounds of the formula VI, in which
  • R 61 and R 62 denote H, F, straight chain alkyl or alkoxy having 1 to 15 C atoms, straight chain alkenyl or alkenyloxy having 2 to 15 C atoms or branched alkyl, alkoxy, alkenyl, alkenyloxy each having 3 to 15 C atoms, where one or more CH2 groups in
  • X 61 , X 62 , X 63 , X 64 , X 65 , and X 66 denote H or F, preferably at least one of X 61 , X 62 , X 63 , X 64 , X 65 , and X 66 denotes F, more preferably at least two of X 61 , X 62 , X 63 , X 64 , X 65 , and X 66 denote F; Z 61 and Z 62 , identically or differently, denote CH2CH2 or a single bond.
  • the compounds of the formula VI are preferably selected from the formulae VI-1 and VI-2: in which the occurring groups have the meanings given for formula VI.
  • the compounds of the formula VI-1 are preferably selected from the formulae VI-1-1 to VI-1-21 , very preferably of the formula VI-1-4: in which R 6 denotes a straight-chain alkyl or alkoxy radical having 1 to 6 C atoms, (O) denotes -O- or a single bond, and m is 0, 1 , 2, 3, 4, 5 or 6 and n is 0, 1 , 2, 3 or 4.
  • R preferably denotes methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.
  • R 6 preferably denotes n-propyl.
  • (O) preferably denotes -O-.
  • the compounds of the formula VI-2 are preferably selected from the formulae VI-2-1 to VI-2-15, very preferably of the formula VI-2-1 :
  • R 6 denotes a straight-chain alkyl or alkoxy radical having 1 to 6 C atoms
  • (O) denotes -O- or a single bond
  • m is 0, 1 , 2, 3, 4, 5 or 6
  • n is 0, 1 , 2, 3 or 4.
  • R preferably denotes methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.
  • the medium additionally comprises one or more compounds of the formulae VI I- 1 to VII-9 in which
  • R 7 denotes a straight-chain alkyl or alkoxy radical having 1 to 6 C atoms, or a straight chain alkenyl radical having 2 to 6 C atoms, and w is an integer from 1 to 6.
  • the medium according to the invention comprises one or more compounds of the formula VIII:
  • R 81 and R 82 identically or differently, denote H, halogen, CN, SCN, straight chain alkyl or alkoxy having 1 to 15 C atoms, straight chain alkenyl or alkenyloxy having 2 to 15 C atoms or branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one
  • -OCF2-, -CH CH-, by -O-, -CO-O- or -O-CO- in such 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, A 0 , A 81 , and A 82 , each, independently of one another, denote phenylene-1 ,4-diyl, in which one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2 or OCFs, cyclohexane-1 ,4-diyl, in which one or two non-adjacent CH2 groups may be replaced, independently of one another, by O and/or S and one or more H atoms may be replaced by F, cyclohexene- 1 ,4- diyl, bicyclo[1.1.1]pentane-1 ,3-d
  • a 81 and A 82 in formula I preferably denote phenylene-1 ,4-diyl, which may also be mono- or polysubstituted by F, furthermore cyclohexane-1 ,4-diyl, cyclohexenylene-1 ,4-diyl, tetrahydropyran-2,5-diyl or 1 ,3-dioxane-2,5-diyl, very preferably phenylene-1 ,4-diyl which may also be mono- or polysubstituted by F, or cyclohexane-1 ,4-diyl.
  • Z 81 and Z 82 in formula VIII preferably denote -CF2O-, -OCF2- or a single bond, very preferably a single bond.
  • a 81 and A 82 in formula VIII particularly preferably denote in which L denotes halogen, CF3 or CN, preferably F.
  • R 81 and R 82 each, independently of one another, denote H, F, or alkyl, alkoxy, alkenyl or alkynyl having 1 to 8, preferably 1 to 5, C atoms, each of which is optionally substituted by halogen, in particular by F.
  • R 81 and R 82 preferably denote H, optionally fluorinated alkyl or alkoxy having 1 to 7 C atoms, optionally fluorinated alkenyl or alkynyl having 2 to 7 C atoms, optionally fluorinated cycloalkyl having 3 to 12 C atoms.
  • R 81 and R 82 are not H, particularly preferably both of R 81 and R 82 are not H.
  • R 81 is very particularly preferably alkyl.
  • R 82 is furthermore preferably H, alkyl or fluorine.
  • R 81 is alkyl and R 82 is H or alkyl.
  • R 81 , R 82 each, independently of one another, very particularly preferably denote unbranched alkyl having 1 to 5 C atoms. If R 81 and R 82 denote substituted alkyl, alkoxy, alkenyl or alkynyl, the total number of C atoms in the two groups R 81 and R 82 is preferably less than 10.
  • Preferred compounds of the formula VIII are selected from the compounds of the formula
  • R 1 and R 2 denote straight chain alkyl having 1 to 15 C atoms, straight chain alkenyl having 2 to 15 C atoms or branched alkyl, or alkenyl having 3 to 15 C atoms, where one or more CH2 groups in these radicals may each be replaced, independently of one another, , and in which one or more H atoms may be replaced by fluorine, preferably both of R 1 and R 2 denote straight chain alkyl having 1 to 6 C atoms.
  • Very preferred compounds of the formula Villa are selected from the compounds of the formulae Vllla-1 to Vllla-35:
  • v is an integer from 1 to 6.
  • R 81 , R 82 and L have the meanings indicated above, L preferably denotes F, and r, s and t independently are 0, 1 , 2, 3, or 4. r preferably is 1 or 2, very preferably 2 and s and t independently are preferably 0 or 1 , very preferably 0. R 81 and R 82 in particular independently denote n-alkyl having 1 to 5 C atoms.
  • the compounds of the formulae VI 11-1 to VIII-6 are selected from the compounds of the formula VII 1-1 a to VI I l-6a, in particular of the formula Vlll-3a: in which R 81 , R 82 , r and s have the meanings defined above.
  • the compounds of the formulae VI 11-1 to VIII-6 are selected from the compounds of the formula VII 1-1 b to VI I l-6b, in particular of the formula 13-b:
  • the compounds of the formulae VII 1-1 to VIII-6 are selected from the compounds of the formula VII 1-1 c to VI ll-6c, in particular of the formula 13-c: in which R 81 , R 82 , L, r and s have the meanings defined above.
  • the compounds of the formulae VI 11-1 to VIII-6 are selected from the compounds of the formula VII 1-1 d to VI I l-6d, in particular of the formula Vlll-3d: in which R 81 , R 82 , L, r and s have the meanings defined above.
  • the medium according to the invention comprises one or more compounds selected from the group of the formulae VIII-1 a to Vlll-6a and one or more compounds selected from the group of the formulae VIII-1 b to Vlll-6b.
  • the medium comprises one or more compounds selected from the group of compounds of the formulae VI I l-3a, VI I l-3b, VI I l-3c and VI I l-3d: in which R 81 , R 82 , L and r have the meanings defined above and preferably r is 0.
  • the medium comprises one or more compounds of the formula
  • R 1 and R 2 identically or differently, denote H, halogen, straight chain alkyl or alkoxy having 1 to 15 C atoms, straight chain alkenyl or alkenyloxy having 2 to 15 C atoms or branched alkyl, alkoxy, alkenyl or alkenyloxy each having 3 to 15 C atoms, where one or more CH2 groups in these radicals may each be replaced, independently of one another,
  • Very preferred compounds of the formula IX are selected from the compounds of the formulae IX- 1 to IX-35
  • R x denote a straight chain or branched alkyl or alkoxy radical having 1 to
  • CF2O-, -OCF2-, -CH CH-, -O-, -CO-O- or -O-CO- in such a way that O atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by halogen, preferably by F,
  • X x denotes F, Cl, CN, SF5, SCN, NCS, a halogenated alkyl radical or a halogenated alkoxy radical each having 1 to 6 C atoms or a halogenated alkenyl radical or a halogenated alkenyloxy radical each having 2 to 6 C atoms
  • R x denotes preferably alkyl with 1 to 6 C atoms or alkenyl with 2 to 6 C atoms which are preferably straight-chain.
  • X x is preferably F, Cl or 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.
  • Preferred compounds of formula X are selected from the following sub-formulae: X7 in which R x has one of the meanings given in formula X and preferably denotes straight-chain alkyl having 1-6 C atoms, very preferably ethyl, propyl, or butyl, or straight-chain alkenyl with 2 to 6 C atoms very preferably vinyl or 1 -propenyl, most preferably vinyl, and X x has one of the meanings given in formula X and preferably denotes F, CF3 or OCF3, very preferably F.
  • the LC medium contains one or more compounds selected from the group consisting of the formulae X1-1, X1-3, X2-1 and X2-3. Further preferred embodiments are listed below: a) Liquid-crystalline medium comprising at least one compound of the formulae Z-1 to Z-8, preferably of the formulae Z-2, Z-4 and Z-6, very preferably Z-4 (O) denotes O or a single bond and alkyl denotes alkyl having 1 to 7 C atoms.
  • Preferred liquid-crystalline media according to the invention comprise one or more substances which contain a tetrahydronaphthyl or naphthyl unit, such as, for example, the compounds of the formulae N-1 to N-5, in which R 1N and R 2N each, independently of one another, have the meanings indicated for R 2A , preferably denote straight-chain alkyl, straight-chain alkoxy or straight-chain alkenyl, and
  • Preferred mixtures comprise one or more compounds selected from the group of the compounds of the formula BC, CR, and PH-1 and PH-2, in which R B1 , R B2 , R CR1 , R CR2 , R P1 , R P2 each, independently of one another, have the meaning of R 31 of formula III; c is 0, 1 or 2.
  • R P1 and R P2 preferably, independently of one another, denote alkyl or alkoxy having 1 to 6 C atoms.
  • Particularly preferred compounds of the formulae BC, CR and PH-1 are the compounds
  • BC-1 to BC-7 CR-1 to CR-5, and BP-1 to BP-7 in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1 to 6 C atoms, and alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2 to 6 C atoms.
  • mixtures comprising one, two or three compounds of the formula BC-2, BC-3, BP-2 and/or BP-3, very preferably BP-2 and/or BP-3, in particular BP-3.
  • Preferred mixtures comprise one or more indane compounds of the formula In, in which
  • R 11 , R 12 , and R 13 each, independently of one another, denote a straight-chain alkyl, alkoxy, alkoxyalkyl or alkenyl radical having 1 to 6 C atoms,
  • R 12 and R 13 alternatively denote halogen, preferably F, i denotes 0, 1 or 2.
  • Preferred compounds of the formula In are the compounds of the formulae ln-1 to In-16 indicated below:
  • Preferred mixtures additionally comprise one or more compounds of the formulae L-1 to L-5, in which R, R 1 and R 2 each, independently of one another, have the meanings indicated for R 2A in formula HA above, and alkyl denotes an alkyl radical having 1 to 6 C atoms.
  • the parameter s denotes 1 or 2.
  • the compounds of the formulae L-1 to L-9 are preferably employed in concentrations of 5 to 15 % by weight, in particular 5 to 12 % by weight and very particularly preferably 8 to 10 % by weight.
  • Preferred mixtures additionally comprise one or more compounds of formula IIA-Y in which R 11 and R 12 have one of the meanings given for R 2A in formula HA above, and L 1 and L 2 , identically or differently, denote F or Cl.
  • Preferred compounds of the formula IIA-Y are selected from the group consisting of the following sub-formulae in which, Alkyl and Alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, Alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms, Alkenyl and Alkenyl* each, independently of one another, denote a straight- chain alkenyl radical having 2-6 C atoms, and O denotes an oxygen atom or a single bond.
  • Particularly preferred compounds of the formula IIA-Y are selected from the group consisting of following sub-formulae:
  • the medium according to the invention comprises a compound selected from the group of compounds of the formulae ST-1 to ST- 18, very preferably of the formula ST- 3:
  • R ST denotes H, an alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one
  • L 1 and L 2 each, independently of one another, denote F, Cl, CH3, CF3 or CHF2, p denotes 0, 1 or 2, q denotes 1 , 2, 3, 4, 5, 6, 7, 8, 9 or 10.
  • n preferably denotes 3.
  • n preferably denotes 7.
  • Very particularly preferred mixtures according to the invention comprise one or more stabilizers from the group of the compounds of the formulae ST-2a-1 , ST-3a-1 , ST- 3b- 1, ST-8-1 , ST-9-1 and ST-12:
  • the medium comprises one or more compounds of the formula S in which Ar denotes a methylene group or an aromatic hydrocarbon group having 6 to 40 C atoms or a heteroaromatic hydrocarbon group having 4 to 40 C atoms; preferably an aromatic hydrocarbon group having 6 to 40 C atoms;
  • Sp denotes a spacer group
  • R s denotes H, alkyl having 1 to 12 C atoms or alkenyl having 2 to 12 C atoms;
  • Z s denotes -O-, -C(O)O-, -(CH 2 ) Z - or -(CH 2 ) Z O-, or a single bond;
  • R H denotes H, O’, CH 3 , OH or OR S ;
  • R S1 , R S2 , R S3 and R S4 identically or differently, denote alkyl having 1 to 6 C atoms, preferably having 1 to 3 C atoms, very preferably CH 3 ;
  • G denotes H or R s or a group Z S -HA; z is an integer from 1 to 6, and q is 2, 3 or 4, preferably 3 or 4.
  • Preferred aryl groups are benzene, naphthalene, anthracene, biphenyl, m-terphenyl, p- terphenyl, and (phenylalkyl)benzene in which alkyl is straight chain alkyl having 1 to 12 C atoms.
  • the medium according to the invention comprises a compound of the formula S in which the parameter q is 3 and G denotes a group
  • the medium according to the invention comprises a compound of the formula S in which the parameter q is 4 and G denotes H or R s .
  • the compounds of formula S are preferably selected from the compounds of the formulae
  • R H has the meanings given above and preferably denotes H or O
  • Sp on each occurrence identically or differently, denotes a spacer group
  • W denotes linear or branched, optionally unsaturated alkylene having 1 to 12 C atoms, in which one or more non-adjacent -CH2- groups may be replaced with -O-.
  • Preferred compounds of formula S-1 are selected from the compounds of the formula S-1- in which R H has the meanings given above and preferably denotes H or O, and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7.
  • Preferred compounds of formula S-2 are selected from the compounds of the formula S-2- 1 :
  • R H has the meanings given above and preferably denotes H or O
  • n2 on each occurrence identically or differently, preferably identically is an integer from 1 to 12, preferably 2, 3, 4, 5, or 6, very preferably 3
  • R s on each occurrence identically or differently, preferably identically denotes alkyl having 1 to 6 C atoms, preferably n-butyl.
  • Preferred compounds of formula S-3 are selected from the compounds of the formula S-3- 1 : in which R H has the meanings given above and preferably denotes H or O, and n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7.
  • the compounds of the formulae S and ST-1 to ST-18 are preferably each present in the liquid-crystal mixtures according to the invention in amounts of 0.005 - 0.5%, based on the mixture.
  • the concentration correspondingly increases to 0.01 - 1% in the case of two compounds, based on the mixtures.
  • the total proportion of the compounds of the formulae S and ST-1 to ST-18, based on the mixture according to the invention, should not exceed 2%.
  • liquid crystal medium according to the invention herein also referred to as liquid crystal host mixture, is suitable for the use in polymer stabilised displays.
  • the medium according to the invention optionally comprises one or more polymerisable compounds of formula P
  • P-Sp-A 1 -(Z 1 -A 2 ) z -R P in which independently of each other and on each occurrence identically or differently, P denotes a polymerisable group
  • Sp denotes a spacer group or a single bond
  • a 1 , A 2 denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, preferably having 4 to 25 ring atoms, which may also contain fused rings, and which is unsubstituted, or mono- or polysubstituted by L,
  • L denotes F, Cl, -CN, P-Sp- or straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by P-Sp-, F or Cl, z is 0, 1 , 2 or 3, and n1 is 1 , 2, 3 or 4.
  • the term "reliability” as used herein means the quality of the performance of the display during time and with different stress loads, such as light load, temperature, humidity, voltage, and comprises display effects such as image sticking (area and line image sticking), mura, yogore etc. which are known to the skilled person in the field of LC displays.
  • VHR voltage holding ration
  • PSA is used hereinafter when referring to displays of the polymer sustained alignment type in general, and the term “PS” is used when referring to specific display modes, like PS-VA, PS-TN and the like.
  • active layer and “switchable layer” mean a layer in an electrooptical display, for example an LC display, that comprises one or more molecules having structural and optical anisotropy, like for example LC molecules, which change their orientation upon an external stimulus like an electric or magnetic field, resulting in a change of the transmission of the layer for polarized or unpolarized light.
  • the tilt angle here denotes the average angle ( ⁇ 90°) between the longitudinal molecular axes of the LC molecules (LC director) and the surface of the plane-parallel outer plates which form the LC cell.
  • ⁇ 90° the average angle
  • a low value for the tilt angle i.e. , a large deviation from the 90° angle
  • tilt angle values disclosed above and below relate to this measurement method.
  • reactive mesogen and "RM” will be understood to mean a compound containing a mesogenic or liquid crystalline skeleton, and one or more functional groups attached thereto which are suitable for polymerisation and are also referred to as “polymerisable group” or "P".
  • polymerisable compound as used herein will be understood to mean a polymerisable monomeric compound.
  • low-molecular-weight compound will be understood to mean to a compound that is monomeric and/or is not prepared by a polymerisation reaction, as opposed to a "polymeric compound” or a "polymer”.
  • unpolymerisable compound will be understood to mean a compound that does not contain a functional group that is suitable for polymerisation under the conditions usually applied for the polymerisation of the RMs.
  • mesogenic group as used herein is known to the person skilled in the art and described in the literature, and means a group which, due to the anisotropy of its attracting and repelling interactions, essentially contributes to causing a liquid-crystal (LC) phase in low-molecular-weight or polymeric substances.
  • Compounds containing mesogenic groups do not necessarily have to have an LC phase themselves. It is also possible for mesogenic compounds to exhibit LC phase behaviour only after mixing with other compounds and/or after polymerisation. Typical mesogenic groups are, for example, rigid rod- or disc-shaped units.
  • optically active and “chiral” are synonyms for materials that are able to induce a helical pitch in a nematic host material, also referred to as “chiral dopants”.
  • spacer group above and below also referred to as “Sp”, as used herein is known to the person skilled in the art and is described in the literature, see, for example, Pure Appl. Chem. 2001 , 73(5), 888 and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368.
  • the terms "spacer group” or “spacer” mean a flexible group, for example an alkylene group, which connects the mesogenic group and the polymerisable group(s) in a polymerisable mesogenic compound.
  • a spacer group connects a central hydrocarbon group with a photoactive, stabilising hindered amine functional group.
  • the single bond shown between the two ring atoms can be attached to any free position of the benzene ring.
  • organic group denotes a carbon or hydrocarbon group.
  • hydrocarbon group denotes a carbon group which additionally contains one or more H atoms and optionally one or more heteroatoms, such as, for example, N, O, S, B, P, Si, Se, As, Te or Ge.
  • Halogen denotes F, Cl, Br or I, preferably F or Cl, very preferably F.
  • a carbon or hydrocarbon group can be a saturated or unsaturated group. Unsaturated groups are, for example, aryl, alkenyl or alkynyl groups.
  • a carbon or hydrocarbon radical having more than 3 C atoms can be straight-chain, branched and/or cyclic and may also contain spiro links or condensed rings.
  • alkyl also encompass polyvalent groups, for example alkylene, arylene, heteroarylene, etc.
  • aryl denotes an aromatic carbon group, or a group derived therefrom.
  • heteroaryl denotes “aryl” as defined above, containing one or more heteroatoms, preferably selected from N, O, S, Se, Te, Si and Ge.
  • Preferred carbon and hydrocarbon groups are optionally substituted, straight-chain, branched or cyclic, alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy having 1 to 40, preferably 1 to 20, very preferably 1 to 12, C atoms, optionally substituted aryl or aryloxy having 5 to 30, preferably 6 to 25, C atoms, or optionally substituted alkylaryl, arylalkyl, alkylaryloxy, arylalkyloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy having 5 to 30, preferably 6 to 25, C atoms, wherein one or more C atoms may also be replaced by hetero atoms, preferably selected from N, O, S, Se, Te, Si and Ge.
  • hetero atoms preferably selected from N, O, S, Se, Te, Si
  • carbon and hydrocarbon groups are C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 allyl, C4-C20 alkyldienyl, C4-C20 polyenyl, C6-C20 cycloalkyl, C4-C15 cycloalkenyl, C6-C30 aryl, C6-C30 alkylaryl, C 6 -C 30 arylalkyl, C6-C30 alkylaryloxy, C6-C30 aryl- alkyloxy, C2-C30 heteroaryl, C2-C30 heteroaryloxy.
  • C1-C12 alkyl Particular preference is given to C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C6-C25 aryl and C2-C25 heteroaryl.
  • R x preferably denotes H, F, Cl, CN, a straight-chain, branched or cyclic alkyl chain having 1 to 25 C atoms, in which, in addition, one or more non-adjacent C atoms may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- and in which one or more H atoms may be replaced by F or Cl, or denotes an optionally substituted aryl or aryloxy group with 6 to 30 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group with 2 to 30 C atoms.
  • Preferred alkyl groups are, 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, perfluorohexyl, etc.
  • Preferred alkenyl groups are, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, etc.
  • Preferred alkynyl groups are, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl, etc.
  • Preferred alkoxy groups are, 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, n-dodecoxy, etc.
  • Preferred amino groups are, for example, dimethylamino, methylamino, methylphenylamino, phenylamino, etc.
  • Aryl and heteroaryl groups can be monocyclic or polycyclic, i.e. , they can contain one ring (such as, for example, phenyl) or two or more rings, which may also be fused (such as, for example, naphthyl) or covalently bonded (such as, for example, biphenyl), or contain a combination of fused and linked rings.
  • Heteroaryl groups contain one or more hetero- atoms, preferably selected from O, N, S and Se.
  • aryl groups having 6 to 25 C atoms and mono-, bi- or tricyclic heteroaryl groups having 5 to 25 ring atoms, which optionally contain fused rings and are optionally substituted.
  • Preferred aryl groups are, for example, phenyl, biphenyl, terphenyl, [1,1':3',1"]terphenyl-2'- yl, naphthyl, anthracene, binaphthyl, phenanthrene, 9,10-dihydro-phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene, indenofluorene, spirobifluorene, etc.
  • Preferred heteroaryl groups are, for example, 5-membered rings, such as pyrrole, pyrazole, imidazole, 1 ,2,3-triazole, 1 ,2,4-triazole, tetrazole, furan, thiophene, selenophene, oxazole, isoxazole, 1,2-thiazole, 1 ,3-thiazole, 1,2,3-oxadiazole,
  • aryl and heteroaryl groups mentioned above and below may also be substituted by alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl or further aryl or heteroaryl groups.
  • the (non-aromatic) alicyclic and heterocyclic groups encompass both saturated rings, i.e. , those containing exclusively single bonds, and also partially unsaturated rings, i.e., those which may also contain multiple bonds.
  • Heterocyclic rings contain one or more heteroatoms, preferably selected from Si, O, N, S and Se.
  • the (non-aromatic) alicyclic and heterocyclic groups can be monocyclic, i.e., contain only one ring (such as, for example, cyclohexane), or polycyclic, i.e., contain a plurality of rings (such as, for example, decahydronaphthalene or bicyclooctane). Particular preference is given to saturated groups. Preference is furthermore given to mono-, bi- or tricyclic groups having 5 to 25 ring atoms, which optionally contain fused rings and are optionally substituted.
  • Preferred alicyclic and heterocyclic groups are, for example, 5-membered groups, such as cyclopentane, tetrahydrofuran, tetrahydrothiophen, pyrrolidine, 6-membered groups, such as cyclohexane, silinane, cyclohexene, tetrahydropyran, tetrahydrothiopyran, 1 ,3-dioxane,
  • substituents are, for example, solubility-promoting groups, such as alkyl or alkoxy, electron-withdrawing groups, such as fluorine, nitro or nitrile, or substituents for increasing the glass transition temperature (Tg) in the polymer, in particular bulky groups, such as, for example, t-butyl or optionally substituted aryl groups.
  • Y 1 denotes halogen
  • Substituted silyl or aryl preferably means substituted by halogen, -CN, R°, -OR 0 , -CO- R°, -CO-O-R 0 , -O-CO-R 0 or -O-CO-O-R 0 , wherein R° denotes H or alkyl with 1 to 20 C atoms.
  • substituents L are, for example, F, Cl, CN, NO2, CH 3 , C2H5, OCH 3 , OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF 3 , OCF 3 , OCHF2, OC2F5, furthermore phenyl.
  • a 1 and A 2 very preferably denote which L has one of the meanings indicated above and r denotes 0, 1 , 2, 3 or 4, in particular
  • the polymerisable group P is a group which is suitable for a polymerisation reaction, such as, for example, free-radical or ionic chain polymerisation, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain.
  • a polymerisation reaction such as, for example, free-radical or ionic chain polymerisation, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain.
  • groups which are suitable for polymerisation with ring opening such as, for example, oxetane or epoxide groups.
  • Phe-CH CH-, HOOC-, OCN- and WWSi-, in which W 1 denotes H, F, Cl, CN, CF 3 , phenyl or alkyl having 1 to 5 C atoms, in particular H, F, Cl or CH 3 , W 2 and W 3 each, independently of one another, denote H or alkyl having 1 to 5 C atoms, in particular H, methyl, ethyl or n-propyl, W 4 , W 5 and W 6 each, independently of one another, denote Cl, oxaalkyl or oxacarbonylalkyl having 1 to 5 C atoms, W 7 and W 8 each, independently of one another, denote H, Cl or alkyl having 1 to 5 C atoms, Phe denotes 1 ,4-phenylene, which is optionally substituted by one or more radicals L as defined above which are other than P-Sp-, ki, k 2 and k 3 each, independently of one another, de
  • polymerisable groups P are selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide, most preferably from acrylate and methacrylate.
  • the spacer group Sp is different from a single bond, it is preferably of the formula Sp"-X", so that the respective radical P-Sp- conforms to the formula R-Sp"-X"-, wherein Sp" denotes linear or branched alkylene having 1 to 20, preferably 1 to 12, C atoms, which is optionally mono- or polysubstituted by F, Cl, Br, I or CN and in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by -O-, -S-,
  • R° and R°° each, independently of one another, denote H or alkyl having 1 to 20 C atoms
  • Y 2 and Y 3 each, independently of one another, denote H, F, Cl or CN.
  • X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR°-CO-, -NR°-CO-NR°°- or a single bond.
  • Typical spacer groups Sp and -Sp"-X"- are, for example, -(CH 2 ) P1 -, -(CH 2 ) P1 -O-, -(CH 2 ) P1 - O-CO-, -(CH 2 ) P1 -CO-O-, -(CH 2 ) P1 -O-CO-O-, -(CH2CH 2 O) q i-CH 2 CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR°R°°-O) p i-, in which p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R° and R°° have the meanings indicated above.
  • Particularly preferred groups Sp and -Sp"-X"- are -(CH 2 ) P1 -, -(CH 2 ) P1 -O-, -(CH 2 ) P1 -O-CO-, - (CH 2 ) P1 -CO-O-, -(CH 2 ) P1 -O-CO-O-, in which p1 and q1 have the meanings indicated above.
  • Particularly preferred groups Sp" are, in each case straight-chain, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methyliminoethylene, 1 -methylalkylene, ethenylene, propenylene and butenylene.
  • the compounds of formula P and its sub- formulae contain a spacer group Sp that is substituted by one or more polymerisable groups P, so that the group Sp-P corresponds to Sp(P) s , with s being >2 (branched polymerisable groups).
  • Preferred compounds of formula P according to this preferred embodiment are those wherein s is 2, i.e., compounds which contain a group Sp(P)2.
  • Very preferred compounds of formula P according to this preferred embodiment contain a group selected from the following formulae:
  • X has one of the meanings indicated for X", and is preferably O, CO, SO 2 , O-CO-, CO- O or a single bond.
  • Preferred spacer groups Sp(P) 2 are selected from formulae S1 , S2 and S3.
  • Very preferred spacer groups Sp(P) 2 are selected from the following sub-formulae: -CHPP S1a
  • P is preferably selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide, most preferably from acrylate and methacrylate.
  • R preferably denotes P-Sp-.
  • Sp denotes a single bond or -(CH 2 ) P1 -, -O-(CH 2 ) P1 -, -O-CO-(CH 2 ) P1 , or -CO-O-(CH 2 ) P1 , wherein p1 is 2, 3, 4, 5 or 6, and, if Sp is -O-(CH 2 ) P1 -, -O-CO-(CH 2 ) P1 or - CO-O-(CH 2 ) P1 the O-atom or CO-group, respectively, is linked to the benzene ring.
  • At least one group Sp is different from a single bond, and is preferably selected from -(CH 2 ) P1 -, -O-(CH 2 ) P1 -, -O-CO-(CH 2 ) P1 , or -CO-O-(CH 2 ) P1 , wherein p1 is 2, 3, 4, 5 or 6, and, if Sp is -O-(CH 2 ) P1 -, -O-CO-(CH 2 ) P1 or -CO-O-(CH 2 ) P1 the O-atom or CO- group, respectively, is linked to the benzene ring.
  • Very preferred groups -A 1 -(Z-A 2 ) z - in formula P are selected from the following formulae wherein at least one benzene ring is substituted by at last one group L and the benzene rings are optionally further substituted by one or more groups L or P-Sp-.
  • Preferred compounds of formula P and their sub-formulae are selected from the following preferred embodiments, including any combination thereof:
  • P is selected from the group consisting of acrylate, methacrylate and oxetane, very preferably acrylate or methacrylate, P is methacrylate, all groups Sp are a single bond, at least one of the groups Sp is a single bond and at least one of the groups Sp is different from a single bond,
  • Sp when being different from a single bond, is -(CH2) P 2-, -(CH2) P 2-O-, -(CH 2 ) P2 -CO-O-, -(CH 2 ) P2 -O-CO-, wherein p2 is 2, 3, 4, 5 or 6, and the O-atom or the CO-group, respectively, is connected to the benzene ring,
  • Sp is a single bond or denotes -(CH 2 ) P2 -, -(CH 2 ) P2 -O-, -(CH 2 ) P2 -CO-O-, -(CH 2 ) P2 -O- CO-, wherein p2 is 2, 3, 4, 5 or 6, and the O-atom or the CO-group, respectively, is connected to the benzene ring,
  • R denotes P-Sp-
  • R does not denote or contain a polymerizable group
  • R does not denote or contain a polymerizable group and denotes straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent de- groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F, Cl or L a ,
  • L or L’ denote F, Cl or CN
  • Suitable and preferred compounds of formula P are selected from the following formulae: in which the individual radicals have the following meanings:
  • P 1 , P 2 and P 3 each, independently of one another, denote an acrylate or methacrylate group
  • Sp 1 , Sp 2 and Sp 3 each, independently of one another, denote a single bond or a spacer group having one of the meanings indicated above and below for Sp, and particularly preferably denote -(CH 2 ) P1 -, -(CH 2 ) P1 -O-, -(CH 2 ) P1 -CO-O-, -(CH 2 ) P1 -O-CO- or -(CH 2 ) P1 -O-CO-O-, in which p1 is an integer from 1 to 12, where, in addition, one or more of the radicals P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - may denote R aa , with the proviso that at least one of the radicals P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - present is different from R aa ,
  • H atoms may be replaced by F, Cl, CN or P 1 -Sp 1 -, particularly preferably straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms (where the alkenyl and alkynyl radicals have at least two C atoms and the branched radicals have at least three C atoms),
  • R°, R°° each, independently of one another and identically or differently on each occurrence denote H or alkyl having 1 to 12 C atoms,
  • R y and R z each, independently of one another, denote H, F, CH3 or CF3, X 1 , X 2 and X 3 each, independently of one another, denote -CO-O-, -O-CO- or a single bond, Z 1 denotes -O-, -CO-, -C(R y R z )- or -CF 2 CF 2 -,
  • Z 2 and Z 3 each, independently of one another, denote -CO-O-, -O-CO-, -CH 2 O-, -OCH 2 -, - CF 2 O-, -OCF 2 - or -(CH 2 ) n -, where n is 2, 3 or 4,
  • L on each occurrence denotes F, Cl, CN or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, preferably F,
  • L' and L" each, independently of one another, denote H, F or Cl, k denotes 0 or 1 , r denotes 0, 1 , 2, 3 or 4, s denotes 0, 1 , 2 or 3, t denotes 0, 1 or 2, x denotes 0 or 1 .
  • trirezine compounds P15 to P30 in particular P17, P18, P19, P22, P23, P24, P25, P26, P30, P31 and P32.
  • the group wherein L on each occurrence, identically or differently, has one of the meanings given above or below, and is preferably F, Cl, CN, NO 2 , CH 3 , C 2 H 5 , C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 )C 2 H 5 , OCH 3 , OC 2 H 5 , COCH 3 , COC 2 H 5 , COOCH 3 , COOC 2 H 5 , CF 3 , OCF 3 , OCHF 2 , OC 2 F 5 or P-Sp-, very preferably F, Cl, CN, CH 3 , C 2 H 5 , OCH 3 , COCH 3 , OCF 3 or P- Sp-, more preferably F, Cl, CH 3 , OCH 3 , COCH 3 Oder OCF 3 , especially F or CH 3 .
  • Very particularly preferred compounds of the formula P are selected from Table E below.
  • the polymerisable compounds contained in the LC medium are polymerised or crosslinked (if one compound contains two or more polymerisable groups) by in-situ polymerisation in the LC medium between the substrates of the LC display, optionally while a voltage is applied to the electrodes.
  • the structure of the PSA displays according to the invention corresponds to the usual geometry for PSA displays, as described in the prior art cited at the outset. Geometries without protrusions are preferred, in particular those in which, in addition, the electrode on the colour filter side is unstructured and only the electrode on the TFT side has slots. Particularly suitable and preferred electrode structures for PS-VA displays are described, for example, in US 2006/0066793 A1.
  • a preferred PSA type LC display of the present invention comprises: a first substrate including a pixel electrode defining pixel areas, the pixel electrode being connected to a switching element disposed in each pixel area and optionally including a micro-slit pattern, and optionally a first alignment layer disposed on the pixel electrode, a second substrate including a common electrode layer, which may be disposed on the entire portion of the second substrate facing the first substrate, and optionally a second alignment layer, an LC layer disposed between the first and second substrates and including an LC medium comprising a polymerisable component comprising one or more compounds of formula R and a liquid crystal host including as described above and below, wherein the polymerisable component may also be polymerised.
  • the first and/or second alignment layer controls the alignment direction of the LC molecules of the LC layer.
  • the alignment layer is selected such that it imparts to the LC molecules homeotropic (or vertical) alignment (i.e. , perpendicular to the surface) or tilted alignment.
  • Such an alignment layer may for example comprise a polyimide, which may also be rubbed, or may be prepared by a photoalignment method.
  • the LC layer with the LC medium can be deposited between the substrates of the display by methods that are conventionally used by display manufacturers, for example the so- called one-drop-filling (ODF) method.
  • ODF one-drop-filling
  • the polymerisable component of the LC medium is then polymerised for example by UV photopolymerisation. The polymerisation can be carried out in one step or in two or more steps.
  • the PSA display may comprise further elements, like a colour filter, a black matrix, a passivation layer, optical retardation layers, transistor elements for addressing the individual pixels, etc., all of which are well known to the person skilled in the art and can be employed without inventive skill.
  • the electrode structure can be designed by the skilled person depending on the individual display type. For example, for PS-VA displays a multi-domain orientation of the LC molecules can be induced by providing electrodes having slits and/or bumps or protrusions in order to create two, four or more different tilt alignment directions.
  • the polymerisable compounds Upon polymerisation the polymerisable compounds form a crosslinked polymer, which causes a certain pretilt of the LC molecules in the LC medium.
  • a crosslinked polymer which causes a certain pretilt of the LC molecules in the LC medium.
  • at least a part of the crosslinked polymer, which is formed by the polymerisable compounds will phase-separate or precipitate from the LC medium and form a polymer layer on the substrates or electrodes, or the alignment layer provided thereon.
  • Microscopic measurement data like SEM and AFM have confirmed that at least a part of the formed polymer accumulates at the LC/substrate interface.
  • the polymerisation can be carried out in one step. It is also possible firstly to carry out the polymerisation, optionally while applying a voltage, in a first step in order to produce a pretilt angle, and subsequently, in a second polymerisation step without an applied voltage, to polymerise or crosslink the compounds which have not reacted in the first step ("end curing").
  • Suitable and preferred polymerisation methods are, for example, thermal or photopolymerisation, preferably photopolymerisation, in particular UV induced photopolymerisation, which can be achieved by exposure of the polymerisable compounds to UV radiation.
  • one or more polymerisation initiators are added to the LC medium.
  • Suitable conditions for the polymerisation and suitable types and amounts of initiators are known to the person skilled in the art and are described in the literature.
  • Suitable for free-radical polymerisation are, for example, the commercially available photoinitiators Irgacure651®, Irgacure184®, lrgacure907®, Irgacure369® or Darocure1173® (Ciba AG).
  • a polymerisation initiator is employed, its proportion is preferably 0.001 to 5% by weight, particularly preferably 0.001 to 1% by weight.
  • the polymerisable compounds according to the invention are also suitable for polymerisation without an initiator, which is accompanied by considerable advantages, such, for example, lower material costs and in particular less contamination of the LC medium by possible residual amounts of the initiator or degradation products thereof.
  • the polymerisation can thus also be carried out without the addition of an initiator.
  • the LC medium thus does not contain a polymerisation initiator.
  • the LC medium may also comprise one or more stabilisers in order to prevent undesired spontaneous polymerisation of the RMs, for example during storage or transport.
  • Suitable types and amounts of stabilisers are known to the person skilled in the art and are described in the literature. Particularly suitable are, for example, the commercially available stabilisers from the Irganox® series (Ciba AG), such as, for example, Irganox® 1076. If stabilisers are employed, their proportion, based on the total amount of RMs or the polymerisable component (component P), is preferably 10-500,000 ppm, particularly preferably 50-50,000 ppm.
  • the polymerisable compounds of formula P in particular show good UV absorption in, and are therefore especially suitable for, a process of preparing a PSA display including one or more of the following features:
  • UV-1 step a first UV exposure step
  • UV-2 step a second UV exposure step
  • the polymerisable medium is exposed to UV light in the display generated by an energy- saving UV lamp (also known as “green UV lamps”). These lamps are characterized by a relative low intensity (1/100-1/10 of a conventional UV1 lamp) in their absorption spectra from 300-380nm, and are preferably used in the UV2 step, but are optionally also used in the UV1 step when avoiding high intensity is necessary for the process.
  • the polymerisable medium is exposed to UV light in the display generated by a UV lamp with a radiation spectrum that is shifted to longer wavelengths, preferably 340nm or more, to avoid short UV light exposure in the PS-VA process.
  • a preferred embodiment of the present invention relates to a process for preparing a PSA display as described above and below, comprising one or more of the following features:
  • UV-1 step a first UV exposure step
  • UV-2 step a second UV exposure step
  • the polymerisable LC medium is exposed to UV light generated by a UV lamp having an intensity of from 0.5 mW/cm 2 to 10 mW/cm 2 in the wavelength range from 300-380nm, preferably used in the UV2 step, and optionally also in the UV1 step,
  • the polymerisable LC medium is exposed to UV light having a wavelength of 340 nm or more, and preferably 400 nm or less.
  • This preferred process can be carried out for example by using the desired UV lamps or by using a band pass filter and/or a cut-off filter, which are substantially transmissive for UV light with the respective desired wavelength(s) and are substantially blocking light with the respective undesired wavelengths.
  • a band pass filter and/or a cut-off filter which are substantially transmissive for UV light with the respective desired wavelength(s) and are substantially blocking light with the respective undesired wavelengths.
  • UV exposure can be carried out using a wide band pass filter being substantially transmissive for wavelengths 300nm ⁇ ⁇ ⁇ 400nm.
  • UV exposure can be carried out using a cut-off filter being substantially transmissive for wavelengths ⁇ > 340 nm.
  • “Substantially transmissive” means that the filter transmits a substantial part, preferably at least 50% of the intensity, of incident light of the desired wavelength(s). “Substantially blocking” means that the filter does not transmit a substantial part, preferably at least 50% of the intensity, of incident light of the undesired wavelengths.
  • “Desired (undesired) wavelength” e.g., in case of a band pass filter means the wavelengths inside (outside) the given range of A, and in case of a cut-off filter means the wavelengths above (below) the given value of A. This preferred process enables the manufacture of displays by using longer UV wavelengths, thereby reducing or even avoiding the hazardous and damaging effects of short UV light components.
  • UV radiation energy is in general from 6 to 100 J, depending on the production process conditions.
  • the LC medium according to the present invention essentially consist of a polymerisable component P) comprising or one or more polymerisable compounds of formula P, and an LC host mixture, and an optically active component comprising one or more chiral dopants, as described above and below.
  • the LC medium according to the present invention optionally comprises one or more further components or additives, preferably selected from the list including but not limited to co-monomers, polymerisation initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricating agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, defoaming agents, deaerators, diluents, reactive diluents, auxiliaries, colourants, dyes, pigments and nanoparticles.
  • further components or additives preferably selected from the list including but not limited to co-monomers, polymerisation initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricating agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, defoaming agents, deaerators, diluents, reactive diluents, auxiliaries, colourants, dyes, pigments and nanoparticles.
  • the liquid-crystalline medium comprises one or more dichroic dyes, preferably in a total amount of 2.0% by weight or less.
  • the total amount of the one or more dichroic dyes in the liquid-crystalline 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.
  • a so-called liquid crystal host is doped with dichroic dye molecules in relatively small, limited amounts. These 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.
  • 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 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.
  • 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.
  • Very preferred dyes are selected from the compounds of the formulae Dye-1 to Dye-9:
  • R denotes straight chain alkyl having 1 to 20 C atoms, or branched alkyl having 3 to 20 C atoms, or straight chain alkenyl having 2 to 20 C atoms, or branched alkenyl having 3 to 20 C atoms, and (O) denotes O or a single bond.
  • LC media comprising one, two or three polymerisable compounds of formula P.
  • the proportion of compounds of formula P in the LC medium is from >0 to
  • ⁇ 5% very preferably from >0 to ⁇ 1%, most preferably from 0.01 to 0.5%.
  • the medium according to the invention preferably comprises one or more compounds of formula S in a total concentration in the range of from 10 ppm to 2000 ppm, more preferably from 100 ppm to 1000 ppm, still more preferably from 150 ppm to 500 ppm, very preferably from 200 ppm to 400 ppm and in particular from 250 to 300 ppm.
  • the medium according to the invention preferably comprises one or more compounds of formula S in a total concentration in the range of from 1000 ppm to 5000 ppm, more preferably from more than 1000 ppm to 5000 ppm, still more preferably from 1200 ppm to 4500 ppm, very preferably from 2000 ppm to 4000 ppm and in particular from 2500 to 3500 ppm.
  • the medium according to the invention preferably has negative dielectric anisotropy.
  • the liquid crystal mixture according to the invention is nematic, preferably at a temperature of -20°C or less, preferably at -30°C or less, very preferably at -40°C or less.
  • liquid-crystalline medium according to the invention prefferably have a nematic phase from ⁇ -20°C to > 90°C, particularly preferably from ⁇ -30°C to > 100°C, very particularly preferably from ⁇ -40°C to > 102°C.
  • the expression "have a nematic phase” herein means on the one hand that no smectic phase and no crystallisation are observed at low temperatures at the corresponding temperature and on the other hand that clearing (phase transition to the isotropic phase) still does not occur on heating from the nematic phase.
  • the investigation at low temperatures is carried out in a flow viscometer at the corresponding temperature and checked by storage in test cells having a layer thickness corresponding to the electro- optical use for at least 100 hours. If the storage stability at a temperature of -20°C in a corresponding test cell is 1000 h or more, the medium is referred to as stable at this temperature. At temperatures of -30°C and -40°C, the corresponding times are 500 h and 250 h respectively. At high temperatures, the clearing point is measured by conventional methods in capillaries.
  • the medium according to the invention has a clearing temperature of 90°C or more, preferably of 98°C or more, more preferably of 100°C or more and in particular of 102°C or more.
  • the liquid-crystal mixture according to the invention has a dielectric anisotropy As of -2.0 to -6.0, preferably of -2.2 to -5.0 , in particular -2.4 to -4.3.
  • the rotational viscosity yi at 20°C is preferably in the range of from 100 to 250 mPas, more preferably from 120 to 235 mPa s.
  • the medium has a birefringence in the range of from 0.070 to 0.120, preferably from 0.075 to 0.118, more preferably from 0.078 to 0.115, in particular from 0.080 to 0.112.
  • the medium has a birefringence in the range of from 0.070 to 0.110, preferably from 0.075 to 0.107, more preferably from 0.078 to 0.105, in particular from 0.080 to 0.102.
  • the medium has a birefringence in the range of from 0.075 to 0.085, preferably from 0.077 to 0.083, more preferably from 0.078 to 0.082, in particular from 0.079 to 0.081.
  • the medium preferably comprises:
  • one or more compounds of the formula I in a concentration in the range of from 1% to 20%, preferably from 2% to 17%, more preferably from 3% to 14%, and very preferably from 4% to 12%; and/or
  • HA preferably HA- 10
  • CCY-n-Om preferably one or more compounds CCY-n-Om, in particular CCY-3-O1 , CCY-3-02, CCY-3-03, CCY-4-02, and/or CCY-5-02, preferably in a total concentration in the range of from 3% to 25%, more preferably from 6% to 20%, particularly preferably from 8% to 15%; and/or
  • one or more compounds of formula HD preferably selected from the compounds of the formulae HD-4 and IID-10, preferably in a total concentration in the range of from 10% to 45%, more preferably, from 15 % to 40%, particularly preferably from 20% to 38%; and/or
  • one or more compounds of formula HD-4 preferably CLY-n-Om, in particular CLY-2-04, CLY-3-02 CLY-3-03, CLY-4-02, and/or CLY-5-02, preferably in a total concentration in the range of from 3% to 30%, more preferably, from 4 % to 28%, particularly preferably from 5% to 25%; and/or
  • one or more compounds of formula HD-10 preferably CLOY-n-Om, in particular CLOY- 3-02, preferably in a total concentration in the range of from 5% to 25%, more preferably, from 10 % to 20%, particularly preferably from 12% to 17%; and/or - less than 5% of one or more compounds of the formula I IB, more preferably less than 3%, very preferably less than 1.5% or 0%; and/or
  • one or more compounds of formula IID-10 preferably CLOY-n-Om, in particular CLOY- 3-02, and one or more compounds of the formula I, preferably CWCY-n-Om, in a total concentration in the range of from 10% to 35%, more preferably, from 15 % to 30%, particularly preferably from 17% to 27%; and/or
  • one or more compounds of the formula III preferably of the formula HI-2 and/or HI-3, more preferably of the formula HI-2-6 and/or HI-3, in particular one or more compounds B(S)-nO-Om and/or COB(S)-n-Om, very particularly B(S)-2O-O4, B(S)-2O-O5, B(S)-2O- 06, B(S)-2O-O1(c5), B(S)-4O-O1(c5), and/or COB(S)-2-O4, preferably in a total concentration in the range of from 0.1% to 20%, more preferably from 0.2% to 17% and very preferably from 0.4% to 15%; and/or
  • one or more compounds of the formula III and/or PH-1 preferably of the formula IH-2 and/or BP-3, more preferably of the formula HI-2-6, in particular selected from B(S)-2O- 04, B(S)-2O-O5 and B(S)-2O-O6, preferably in a total concentration in the range of from 1 % to 12%, more preferably from 2% to 11% and very preferably from 3% to 10%; and/or
  • one or more compounds of the formula III preferably of the formula HI-2 and HI-3, more preferably of the formula HI-2-6 and HI-3, in particular one or more compounds B(S)-nO- Om and COB(S)-n-Om, very particularly B(S)-2O-O4, B(S)-2O-O5, B(S)-2O-O6, and COB(S)-2-O4, preferably in a total concentration in the range of from 4% to 20%, more preferably from 6% to 14% and very preferably from 8% to 12%; and/or - one or more compounds of formula IV, preferably in a total concentration in the range of from 25% to 60%, more preferably from 30 % to 50%, particularly preferably from 32% to 45%; and/or
  • one or more compounds of the formula VI-1 preferably IV-1-6, preferably in a total concentration in the range of from 1% to 20%, more preferably from 2% to 18% and very preferably from 3% to 15%; and/or
  • the compound(s) of the formula CC-3-V1 and/or CC-4-V1 in a total concentration in the range of from 5 to 35%, more preferably from 10% to 30%, particularly preferably from 18% to 28%, and/or
  • one or more compounds of the formula IV-3-1 preferably CC-3-V and/or CC-4-V, preferably in a total concentration in the range of from 1% to 25%, more preferably from 2% to 22% and very preferably from 3% to 20%; and/or
  • one or more compounds of the formula IVa more preferably of the formula IVa-2, in particular CP-3-02, in a total concentration in the range of from 0.5% to 8%, more preferably from 1% to 6%, very preferably from 2% to 5%; and/or
  • one or more compounds of the formula V more preferably selected from the compounds of the formulae V-2-1 and V-2-2, in particular CCP-n-m and/or CCP-Vn-m and/or CPP-n- m, very particularly selected from the group consisting of CCP-3-1, CCP-V-1, CCP-V2-1 and CPP-3-2, preferably in a total concentration in the range of from 1% to 20%, more preferably from 2% to 17%, very preferably from 3% to 14%; and/or
  • the medium according to the invention comprises
  • one or more compounds of the formula I in a concentration in the range of from 1% to 15%, preferably from 2% to 10%, more preferably from 3% to 8%, and very preferably from 4% to 6%; and/or one or more compounds of the formula 11 A, preferably IIA-10, more preferably one or more compounds CCY-n-Om, in particular CCY-4-02, CCY-3-02, CCY-3-03, CCY-3-O1 and/or CCY-5-02, very particularly CCY-3-02 and CCY-5-02, in a total concentration in the range of from 10% to 35%, more preferably from 15% to 30%, very preferably from 20% to 25%; and/or one or more compounds of the formula IID-L1 in a total concentration in the range of from 1 % to 15%, more preferably from 3% to 10%, very preferably from 5% to 8%; and/or one or more compounds of the formula IID-L2 in a total concentration in the range of from 5% to 25%, more preferably from 10% to 20%, very preferably from preferably
  • one or more compounds of the formula IIA-Y preferably of the formula IIA-Y6 and/or HA- YS, more preferably of the formula IIA-Y6a, in particular the compound Y-4O-O4, preferably in a concentration in the range of from 1% to 10%, more preferably from 2% to 9%, very preferably from 3% to 8%, in particular from 4% to 7%; and/or
  • one or more compounds of the formula III preferably of the formula HI-2 and HI-3, more preferably of the formula HI-2-6 and HI-3, very preferably 111-2-6, in particular one or more compounds B(S)-nO-Om, very particularly selected from B(S)-2O-O4, B(S)-2O-O5, and B(S)-2O-O6, preferably in a total concentration in the range of from 0.1 % to 5%, more preferably from 0.2% to 4%, very preferably from 0.3% to 3%, in particular from 0.4% to 2% or from 0.5% to 1 %; and/or one or more compounds of the formula IV, more preferably of the formulae IV-1 and I -2 and IV-3 in a total concentration in the range of from 25% to 65%, more preferably from 30% to 55%, very preferably from 35% to 50% in particular 38% to 47%, very particularly 40% to 47%; and/or one or more compounds of the formula IV-1 , more preferably selected from the compounds of the formulae IV-1-1-1
  • the medium according to the invention preferably comprises one or more stabilizer, very preferably:
  • the compound ST-2a-1 in a concentration in the range of from 5 to 500 ppm, preferably from 10 to 250 ppm, more preferably from 15 to 100 ppm, in particular from 20 to 75 ppm; and/or
  • the compound BHT in a concentration in the range of from 10 to 1000 ppm, preferably from 20 to 750 ppm, more preferably from 50 to 500 ppm, in particular from 100 to 200 ppm; and/or
  • the compound ST-3a-1 in a concentration in the range of from 10 to 1500 ppm, preferably from 100 to 1000 ppm, more preferably from 200 to 750 ppm, in particular from 300 to 500 ppm; and/or
  • the compound Irgafos® 168 in a concentration in the range of from 5 to 500 ppm, preferably from 20 to 250 ppm, more preferably from 40 to 150 ppm, in particular from 50 to 100 ppm.
  • liquid-crystal media according to the invention have high values for the voltage holding ratio in liquid-crystal cells.
  • liquid-crystal media having a low addressing voltage or threshold voltage exhibit a lower voltage holding ratio than those having a higher addressing voltage or threshold voltage and vice versa.
  • dielectrically positive compounds denotes compounds having a As > 1.5
  • dielectrically neutral compounds denotes those having -1.5 ⁇ As ⁇ 1.5
  • dielectrically negative compounds denotes those having As ⁇ -1.5.
  • the dielectric anisotropy of the compounds is determined here by dissolving 10 % of the compounds in a liquid-crystalline host and determining the capacitance of the resultant mixture in at least one test cell in each case having a layer thickness of 20 pm with homeotropic and with homogeneous surface alignment at 1 kHz.
  • the measurement voltage is typically 0.5 V to 1.0 V but is always lower than the capacitive threshold of the respective liquid-crystal mixture investigated.
  • the mixtures according to the invention are suitable for all VA-TFT applications, such as, for example, VAN, MVA, (S)-PVA, ASV, PSA (polymer sustained VA) and PS-VA (polymer stabilized VA). They are furthermore suitable for IPS (in-plane switching) and FFS (fringe field switching) applications having negative As, in particular LIB-FFS.
  • VA, IPS or FFS mixture according to the invention may also comprise compounds in which, for example, H, N, O, Cl and F have been replaced by the corresponding isotopes.
  • the compounds according to the present invention can be synthesized by or in analogy to known methods described in the literature (for example in the standard works such as Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), under reaction conditions which are known and suitable for said reactions. Use may also be made here of variants which are known per se but are not mentioned here. In particular, they can be prepared as described in or in analogy to the following reaction schemes. Further methods for preparing the inventive compounds can be taken from the examples. Other mesogenic compounds which are not explicitly mentioned above can optionally and advantageously also be used in the media in accordance with the present invention. Such compounds are known to the person skilled in the art.
  • Table A shows the codes for the ring elements of the nuclei of the compound
  • Table B lists the bridging units
  • Table C lists the meanings of the symbols for the left- and right-hand end groups of the molecules.
  • the acronyms are composed of the codes for the ring elements with optional linking groups, followed by a first hyphen and the codes for the left-hand end group, and a second hyphen and the codes for the right-hand end group.
  • Table D shows illustrative structures of compounds together with their respective abbreviations.
  • the mixtures according to the invention optionally comprise one or more compounds of the compounds mentioned below.
  • the following abbreviations are used:
  • n, m, k and I are, independently of one another, each an integer, preferably 1 to 9 preferably 1 to 7, k and I possibly may be also 0 and preferably are 0 to 4, more preferably 0 or 2 and most preferably 2, n preferably is 1 , 2, 3, 4 or 5, in the combination “-nO-” it preferably is 1 , 2, 3 or 4, preferably 2 or 4, m preferably is 1 , 2, 3, 4 or 5, in the combination “-Om” it preferably is 1 , 2, 3 or 4, more preferably 2 or 4.
  • the combination IVm” preferably is “2V1”.
  • Table E shows illustrative reactive mesogenic compounds which can be used in the LC media in accordance with the present invention.
  • the mixtures according to the invention comprise one or more polymerizable compounds, preferably selected from the polymerizable compounds of the formulae RM-1 to RM-182.
  • threshold voltage for the present invention relates to the capacitive threshold (Vo), also known as the Freedericks threshold, unless explicitly indicated otherwise.
  • the optical threshold may also, as generally usual, be quoted for 10% relative contrast (Vw).
  • the process of polymerising the polymerisable compounds in the PSA displays as described above and below is carried out at a temperature where the LC medium exhibits a liquid crystal phase, preferably a nematic phase, and most preferably is carried out at room temperature.
  • the display used for measurement of the capacitive threshold voltage consists of two plane-parallel glass outer plates with a distance of 25 pm, each of which has on the inside an electrode layer and an unrubbed polyimide alignment layer on top, which effect homeotropic alignment of the liquid-crystal molecules.
  • the display or test cell used for measurement of the tilt angles consists of two plane- parallel glass outer plates at a separation of 4 pm, each of which has on the inside an electrode layer and a polyimide alignment layer on top, where the two polyimide layers are rubbed antiparallel to one another and effect a homeotropic edge alignment of the liquid- crystal molecules.
  • the polymerisable compounds are polymerised in the display or test cell by irradiation with UV light of defined intensity for a prespecified time, with a voltage simultaneously being applied to the display (usually 10 V to 30 V alternating current, 1 kHz).
  • a fluorescent lamp and an intensity of 0 to 20 mW/cm 2 is used for polymerisation. The intensity is measured using a standard meter (llshio Accumulate UV meter with central wavelength of 313nm).
  • the transmission measurements are performed in test cells with fishbone electrode layout (from Merck Ltd., Japan; 1 pixel fishbone electrode (ITO, 10x10 mm, 47.7° angle of fishbone with 3pm line/3pm space), 3.2 pm cell gap, AF-glass, tilt angle 1°).
  • fishbone electrode layout from Merck Ltd., Japan; 1 pixel fishbone electrode (ITO, 10x10 mm, 47.7° angle of fishbone with 3pm line/3pm space), 3.2 pm cell gap, AF-glass, tilt angle 1°).
  • the storage stability in the bulk (LTSbuik) of the media according to the invention at a given temperature T is determined by visual inspection.
  • 2 g of the media of interest are filled into a closed glass vessel (bottle) of appropriate size placed in a refrigerator at a predetermined temperature.
  • the bottles are checked at defined time intervals for the occurrence of smectic phases or crystallisation. For every material and at each temperature two bottles are stored. If crystallisation or the appearance of a smectic phase is observed in at least one of the two correspondent bottles the test is terminated and the time of the last inspection before the one at which the occurrence of a higher ordered phase is observed is recorded as the respective storage stability.
  • the Comparative Example C1 and the Mixture Examples M1 to M33 and P1 to P10 have the compositions and properties given in the following tables. The quantities in these tables are given in percent by weight.
  • the mixture Examples M1 to M25 contain stabilisers as given in the following table:
  • Mixture Example M26 consists of Mixture Example M1 and further comprises 50 ppm of the compound ST-2a-1 , 500 ppm of the compound ST-3a-1 and 50 ppm of the compound ST-9-1
  • Mixture Example M27 consists of Mixture Example M2 and further comprising 150 ppm of the compound BHT, 350 ppm of the compound ST-3a-1 and 50 ppm of the compound ST-2a-1
  • Mixture Example M28 consists of Mixture Example M3 and further comprising 200 ppm of the compound BHT, 50 ppm of the compound ST-2a-1, 350 ppm of the compound ST-3a-1, and 100 ppm of the compound Irgafos 168®
  • the polymerisable mixtures P1 to P9 are prepared from the nematic mixtures given in
  • the polymerisable mixture P10 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 the compound ST-3a-1.

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Abstract

La présente invention concerne un matériau à cristaux liquides (LC) tel que défini dans la revendication 1, ayant une anisotropie diélectrique négative et son utilisation à des fins optiques, électro-optiques et électroniques, telles que par exemple dans des affichages LC, en particulier des affichages éco-énergétiques basés sur l'effet ECB, IPS ou FFS.
PCT/EP2025/056317 2024-03-11 2025-03-07 Milieu à cristaux liquides Pending WO2025190813A1 (fr)

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