WO2022184604A1 - Milieu à cristaux liquides - Google Patents

Milieu à cristaux liquides Download PDF

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WO2022184604A1
WO2022184604A1 PCT/EP2022/054906 EP2022054906W WO2022184604A1 WO 2022184604 A1 WO2022184604 A1 WO 2022184604A1 EP 2022054906 W EP2022054906 W EP 2022054906W WO 2022184604 A1 WO2022184604 A1 WO 2022184604A1
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atoms
compounds
formula
denotes
alkyl
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PCT/EP2022/054906
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Yuyun LIU
Yang Huang
Yu SHUO
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Merck Patent Gmbh
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Priority to CN202280013417.4A priority Critical patent/CN116964177A/zh
Publication of WO2022184604A1 publication Critical patent/WO2022184604A1/fr

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    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • 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
    • C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
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    • C09K19/00—Liquid crystal materials
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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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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/122—Ph-Ph
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    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/123—Ph-Ph-Ph
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • 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)
    • C09K2019/3004—Cy-Cy
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • 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)
    • C09K2019/3009—Cy-Ph
    • C—CHEMISTRY; METALLURGY
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    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • 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)
    • C09K2019/301—Cy-Cy-Ph
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • 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

Definitions

  • the present invention relates to a liquid-crystal (LC) medium comprising a stabiliser, to its use for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the vertically aligned mode, to an LC display of the vertically aligned mode comprising the LC medium, and to a process of manufacturing the LC display.
  • LC liquid-crystal
  • the popularity of 8K and gaming monitors leads to an increased need for LC display (LCD) panels having higher refresh rates and thus for LC media having faster response times. Many of these LCD panels are using display modes wherein the LC molecules are aligned substantially perpendicular or slightly tilted relative to the electrode surface in the switched-off state.
  • 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 value of the dielectric anisotropy ( ⁇ ).
  • ⁇ dielectric anisotropy
  • the molecules of the LC layer are aligned perpendicular to the electrode surfaces (homeotropically) or have a tilted homeotropic alignment.
  • FFS field switching
  • FFS displays have a low viewing-angle dependence of the contrast.
  • FFS displays usually contain an LC medium with positive dielectric anisotropy, and an alignment layer, usually of polyimide, which provides planar alignment to the molecules of the LC medium.
  • FFS displays can be operated as active-matrix or passive-matrix displays.
  • IPS in-plane switching
  • 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 favourable director orientation that has less tilt and more twist orientation compared to the LC medium with positive dielectric anisotropy, as a result of which these displays have a higher transmission.
  • VA displays which use an alignment layer that is prepared by photoalignment, also known as UV 2 A mode (see e.g. Q. Tang et al., SID Symposium Digest of Technical Papers 2018, 414-417).
  • These displays utilize an alignment layer prepared from crosslinkable and photoorientable monomers or prepolymers, e.g. cinnamate chromophores which are irradiated obliquely with linearly polarized UV light.
  • crosslinked alignment layer is formed which induces uniaxial alignment with a pretilt angle in the LC molecules close to its surface.
  • LC media with negative dielectric anisotropy have also several drawbacks. For example, they have a significantly lower reliability compared to LC media with positive dielectric anisotropy.
  • the term "reliability” as used hereinafter means the quality of the performance of the display during time and with different stress loads, such as light load, temperature, humidity, or voltage which cause display defects such as image sticking (area and line image sticking), mura, yogore etc. and which are known to the skilled person in the field of LC displays.
  • VHR voltage holding ration
  • the reduced reliability of an LC medium with negative dielectric anisotropy in a VA or FFS display can be explained by an interaction of the LC molecules with the polyimide of the alignment layer, as a result of which ions are extracted from the polyimide alignment layer, and wherein LC molecules with negative dielectric anisotropy do more effectively extract such ions.
  • the LC medium has to show a high reliability and a high VHR value after UV exposure.
  • the UV component of daylight or the backlight can cause undesired decomposition reactions of the LC molecules therein and thus initiate the production of ionic or free-radical impurities. These may accumulate, in particular, at the electrodes or the alignment layers, where they may reduce the effective applied voltage.
  • LC media for use in displays including but not limited to VA and FFS displays, do often exhibit high viscosities and, as a consequence, high switching times. In order to reduce the viscosity and switching time of the LC medium, it has been suggested in prior art to add LC compounds with an alkenyl group.
  • 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 but also to visible light from the backlight of a display, that usually does not emit UV light.
  • the use of stabilisers was proposed, such as for example compounds of the HALS- (hindered amine light stabiliser) type.
  • HALS- hindered amine light stabiliser
  • Tinuvin 770 a compound of the formula Nevertheless, these LC mixtures can still exhibit insufficient reliability during the operation of a display, e.g. upon irradiation with the typical CCFL-(Cold Cathode Fluorescent Lamp) backlight.
  • a different class of compound used for the stabilisation of liquid crystals are antioxidants derived from phenol, such as for example the compound as described in DE 19539141 A1.
  • Such stabilisers can be used to stabilise LC mixtures against heat or the influence of oxygen but typically do not show advantages under light stress.
  • the liquid crystal a complex mixture of many different types of compounds itself, interacts with different kinds of species, including the polyimide, it is a challenging task also for the skilled person to choose the right stabiliser in order to identify the best material combination.
  • a further object of the invention is to provide FFS displays with good transmission, high reliability, a VHR value especially after backlight exposure, a high specific resistance, a large working-temperature range, short response times even at low tempera- tures, a low threshold voltage, a multiplicity of grey levels, high contrast and a broad viewing angle, and reduced image sticking. It was found that one or more of these objects could be achieved by providing an LC medium as disclosed and claimed hereinafter.
  • an LC medium comprising a small amount of a stabiliser, which is a compound of formula I as described hereinafter, in a VA-, IPS or FFS display. It has also been found that when using such stabilisers in an LC medium for use in an FFS display, surprisingly the reliability and the VHR value after backlight load are higher, compared to an LC medium without a stabiliser according to the present invention. Also, the use of an LC medium comprising a stabiliser as described hereinafter allows to exploit the known advantages of alkenyl-containing LC media, like reduced viscosity and faster switching time, and at the same time leads to improved reliability and high VHR value especially after backlight exposure.
  • a stabiliser which is a compound of formula I as described hereinafter
  • the invention further relates to the use of the LC medium as described above and below in LC displays, preferably in LC displays of the VA, IPS, FFS, UB-FFS or UV 2 A mode.
  • the LC medium has negative dielectric anisotropy.
  • 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 formula I with one or more compounds of formula II and optionally with further LC compounds and/or additives.
  • the invention furthermore relates to an LC display comprising an LC medium according to the invention as described above and below, preferably an LC display of the VA, IPS, FFS, UB-FFS or UV 2 A mode.
  • 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 as described above and below between the substrates of the display.
  • the compounds of formula I although they carry potentially reactive groups P like acrylate or methacrylate, quite contrary to being harmful in terms of reliability of the LC, are able to stabilise LC mixtures under light stress. It was also found that, if the concentration of the compounds of formula I is kept low enough, an undesired generation of a pretilt angle in the LC medium, which is usually observed when using such compounds in VA mode displays and exposing them to UV irradiation, can be suppressed.
  • the reliability and the VHR value after backlight load are higher, compared to an LC medium without a compound of formula I according to the present invention.
  • the use of an LC medium comprising a compound of formula I as described hereinafter allows to exploit the known advantages of alkenyl- containing LC media, like reduced viscosity and faster switching time, and at the same time leads to improved reliability and high VHR value especially after backlight exposure.
  • the compounds of formula I are preferably selected from achiral compounds.
  • the terms “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 terms “tilt” and “tilt angle” will be understood to mean a tilted alignment of the LC molecules of an LC medium relative to the surfaces of the cell in an LC display (here preferably a PSA display), and will be understood to be inclusive of “pretilt” and "pretilt angle”.
  • 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.
  • a low absolute value for the tilt angle i.e. a large deviation from the 90° angle
  • a suitable method for measurement of the tilt angle is given in the examples. Unless indicated otherwise, tilt angle values disclosed above and below relate to this measurement method.
  • 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.
  • LC liquid-crystal
  • 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 polymerization. Typical mesogenic groups are, for example, rigid rod- or disc-shaped units.
  • spacer group hereinafter 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.
  • spacer group or "spacer” mean a flexible group, for example an alkylene group, which connects the mesogenic group and the polymerizable group(s) in a polymerizable mesogenic compound.
  • alkylene group which connects the mesogenic group and the polymerizable group(s) in a polymerizable mesogenic compound.
  • the single bond shown between the two ring atoms can be attached to any free position of the benzene ring.
  • R 1-12 , R Q , R or L denotes an alkyl radical and/or an alkoxy radical, this may be straight- chain or branched.
  • It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetra- decyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.
  • R 1-13 R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L denotes an alkyl radical and/or an alkoxy radical, this may be straight-chain or branched.
  • It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.
  • R 1-13 R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L denotes an alkyl radical wherein one or more CH 2 groups are replaced by S, this may be straight-chain or branched. It is preferably straight-chain, has 1, 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes thiomethyl, thioethyl, thiopropyl, thiobutyl, thiopentyl, thiohexyl or thioheptyl.
  • R 1-13 R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L denotes an alkoxy or oxaalkyl group it may also contain one or more additional oxygen atoms, provided that oxygen atoms are not linked directly to one another.
  • one or more of R 1-13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L are selected from the group consisting of -S 1 -F, -O-S 1 -F, -O-S1-O-S2, wherein S 1 is C 1-12 -alkylene or C 2-12 - alkenylene and S 2 is H, C 1-12 -alkyl or C 2-12 -alkenyl, and very preferably are selected from the group consisting of -OCH 2 OCH 3 , -O(CH 2 ) 2 OCH 3 , -O(CH 2 ) 3 OCH 3 , -O(CH 2 ) 4 OCH 3 , -O(CH 2 ) 2 F, - O(CH 2 ) 3 F and -O(CH 2
  • R 1-13 R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L denotes an alkyl or alkenyl radical which is at least monosubstituted by halogen, this radical is preferably straight-chain, and halogen is preferably F or Cl. In the case of polysubstitution, halogen is preferably F.
  • the resultant radicals also include perfluorinated radicals.
  • the fluorine or chlorine substituent may be in any desired position, but is preferably in the ⁇ -position.
  • Halogen is preferably F or Cl, very preferably F.
  • substituents L are, for example, F, Cl, CN, NO 2 , 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 , furthermore phenyl.
  • L has one of the meanings indicated above.
  • the group P is preferably selected from the group consisting of acrylate, methacrylate, fluoroacrylate and chloroacrylate, more preferably from acrylate and methacrylate, most preferably P denotes methacrylate.
  • X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 - CO-, -NR 0 -CO-NR 00 - or a single bond.
  • Typical spacer groups Sp 1-3 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-, - (CH 2 CH 2 O) q1 -CH 2 CH 2 -, -CH 2 CH 2 -S-CH 2 CH 2 -, -CH 2 CH 2 -NH-CH 2 CH 2 - or - (SiR 0 R 00 -O) p1 -, in which p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 0 and R 00 have the meanings indicated above.
  • Particularly preferred groups Sp 1-3 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.
  • Preferred compounds of formula I and its subformulae are those wherein at least one of the groups Sp 1-3 is a single bond.
  • Further preferred compounds or formula I and its subformulae are those wherein at least one of the groups Sp 1-3 is different from a single bond.
  • Very preferred are compounds of formula I and its subformulae, wherein Sp 1-3 are selected from the group consisting of a single bond, -(CH 2 ) p1 -, - O-(CH 2 ) p1 -, -O-CO-(CH 2 ) p1 and -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.
  • - all groups P have the same meaning, and very preferably denote acrylate or methacrylate, most preferably methacrylate, - all of Sp 1-3 are a single bond - all of Sp 1-3 are different from a single bond, - one of Sp 1-3 is a single bond and the other two are different from a single bond, - one of Sp 1-3 is different from a single bond and the other two each denote a single bond, - Sp 1 is a single bond and one or both of Sp 2 and Sp 3 , preferably both of Sp 2 and Sp 3 , are different from a single bond, - Sp 1-3 , when being different from a single bond, are selected from the group consisting of -(CH 2 ) 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 -, -O-(CH 2 ) 2 -, -O
  • Sp’ in formulae I1 to I8 is preferably selected from the group consisting of - (CH 2 ) 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 -, -O-(CH 2 ) 2 -, -O-(CH 2 ) 3 -, -O-CO-(CH 2 ) 2 and -CO- O-(CH) 2 -, wherein the O atom or the CO group is attached to the benzene ring.
  • L in formulae I1 to I8 preferably denotes F, Cl, CN or OCH 3 , very preferably F or OCH 3 .
  • Very preferred compounds of formula I are selected from the following subformulae:
  • concentration of the compounds of formula I and its subformulae in the LC medium is preferably from 0.001 to 0.02%, very preferably from 0.002 to 0.015%, most preferably from 0.005 to 0.015%. In another rpreferred embodiment the concentration of the compounds of formula I and its subformulae in the LC medium is from 10 to 250ppm, preferably from 20 to 200ppm, most preferably from 50 to 150 ppm.
  • the compounds of the formula I can be prepared analogously to processes known to the person skilled in the art and described in standard works of organic chemistry, such as, for example, in Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Thieme-Verlag, Stuttgart.
  • acrylic or methacrylic esters can be prepared by esterification of the corresponding alcohols with acid derivatives like, for example, (meth)acryloyl chloride or (meth)acrylic anhydride in the presence of a base like pyridine or triethyl amine, and 4-(N,N-dimethylamino)pyridine (DMAP).
  • the esters can be prepared by esterification of the alcohols with (meth)acrylic acid in the presence of a dehydrating reagent, for example according to Steglich with dicyclohexylcarbodiimide (DCC), N-(3- dimethylaminopropyl)-N’-ethylcarbodiimide (EDC) or N-(3- dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride and DMAP.
  • the LC media for use in the LC displays according to the invention comprise an LC mixture ("host mixture") comprising one or more, preferably two or more LC compounds, at least one of which is a compound of formula II. Particularly preferred embodiments of such an LC medium are shown below.
  • the LC medium contains one or more compounds of formula II selected from the group consisting of compounds of the formulae IIA, IIB, IIC and IID
  • R 2A and R 2B each, independently of one another, denote H, an alkyl or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF 3 or at least monosubstituted by halogen, where, in addition, one or more CH 2 groups in these radicals may be replaced by -O-, -S-, -C ⁇ C-, -CF 2 O-, -OCF 2 -, -OC-O- or -O-CO- in such a way that O atoms are not linked directly to one another, L 1 to L 4 each, independently of one another, denote F, Cl, CF 3 or CHF 2 , Y denotes H, F, Cl, CF 3 , CHF 2 or CH 3 , preferably H or CH 3 , particularly preferably H, Z 2 , Z 2B and Z 2D each, independently of one another, denote a single bond, -CH 2 CH 2 -,
  • Preferred compounds of the formulae IIA, IIB, IIC and IID are those wherein R 2B denotes an alkyl or alkoxy radical having up to 15 C atoms, and very preferablydenotes (O)C v H 2v+1 wherein (O) is an oxygen atom or a single bond and v is 1, 2, 3, 4, 5 or 6.
  • LC medium comprises one or more compounds of the formula IIA selected from the group consisting of formulae IIA-1 to IIA-76,
  • index a denotes 1 or 2
  • alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms
  • alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms
  • (O) denotes an oxygen atom or a single bond.
  • Particularly preferred LC media according to the invention comprise one or more compounds selected from the group consisting of formulae IIA-2, IIA- 8, IIA-10, IIA-16, II-18, IIA-40, IIA-41, IIA-42 and IIA-43.
  • the LC medium comprises one or more compounds of the formula IIB selected from the group consisting of formulae IIB-1 to IIB-26,
  • LC media comprise one or more compounds selected from the group consisting of formulae IIB-2, IIB- 10 and IIB-16.
  • the LC medium comprises one or more compounds of the formula IIC selected from the formula IIC-1, in which “alkyl” and “alkyl*” and (O) have the meanings given above.
  • the LC medium comprises one or more compounds of the formula IID selected from the group consisting of formulae IID-1 to IID-10,
  • Particularly preferred LC media according to the invention comprise one or more compounds of the formula IID-4.
  • the proportion of compounds of the formulae IIA and/or IIB in the mixture as a whole is preferably at least 20 % by weight.
  • the LC medium comprises one or more compounds of the formula III-1 and/or III-2 in which the occurring groups have the same meanings as given under formula III above and preferably R 11 and R 12 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 11 and L 12 each preferably denote F.
  • the LC medium comprises one or more compounds of the formula III-1 selected from the group consisting of formulae III-1-1 to III-1-11, preferably of formula III-1-6, 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 11 and L 12 each, independently of one another, denote F or Cl, preferably both F.
  • the LC medium comprises one or more compounds of the formula III-2 selected from the group consisting of formulae III-2-1 to III-2-10, preferably of formula III-2-6,
  • 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
  • L 11 and L 12 each, independently of one another, denote F or Cl, preferably both F.
  • the LC medium comprises one or more compounds selected from the group consisting of the following formulae
  • the LC medium comprises one or more compounds of the formula IIIA-1 and/or IIIA-2 in which L 11 and L 12 have the same meanings as given under formula III, (O) denotes O or a single bond, R IIIA denotes alkyl or alkenyl having up to 7 C atoms or a group Cy- C m H 2m+1 -, m and n are, identically or differently, 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, and 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 or cyclopentyl.
  • the compounds of formula IIIA-1 and/or IIIA-2 are contained
  • alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms, and preferably denotes n-propoxy, n-butyloxy, n-pentyloxy or n- hexyloxy.
  • the compounds of formula III-3 are preferably selected from the group consisting of formulae III-3-1 to III-3-11:
  • the LC medium comprises one or more compounds of the formulae III-4 to III-6, preferably of formula III-5,
  • the LC medium comprises one or more compounds of the formula I selected from the group consisting of formulae III-7 to III-9, preferably of formula III-8, in which the parameters have the meanings given above, R 11 preferably denotes straight-chain alkyl and R 12 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 unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted 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 unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkoxy radical having 1 to 6 C atoms, both preferably having 2 to 5 C atoms, an unsub- stituted 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.
  • R 41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms, preferably an
  • the compounds of the formula IV are preferably selected from the group consisting of formulae IV-1 to IV-6, in which “alkyl” and “alkyl*“ independently of one another, denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, “alkenyl” denotes an alkenyl radical having 2 to 5 C atoms, prefer- ably having 2 to 4 C atoms, particularly preferably 2 C atoms, “alkenyl*“ denotes an alkenyl radical having 2 to 5 C atoms, prefer- ably 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 LC medium comprises one or more compounds selected from the group consisting of formulae IV-1-1 to IV-1-9
  • the LC medium according to the invention comprises one or more compounds of the formulae IV-2-1 and/or IV-2-2
  • the LC medium according to the invention comprises a compound of formula IV-3, in particular selected from the group consisting of formulae IV-3-1 to IV-3-4
  • the LC medium according to the invention comprises a compound of formula IV-4, in particular selected from the compounds of the formulae IV-4-1 and IV-4-2
  • the LC medium according to the invention preferably comprises at least one compound of the formula IVa-1and/or formula IVa-2.
  • the LC medium comprises one or more compounds of formula 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 proportion of the biphenyls of the formulae IV-1 to IV-3 in the mixture as a whole is preferably at least 3 % by weight, in particular ⁇ 5 % by weight.
  • the compounds of the formula IVb-2 are particularly preferred.
  • Particularly preferred biphenyls are in which “alkyl*” denotes an alkyl radical having 1 to 6 C atoms and preferably denotes n-propyl.
  • the LC medium according to the invention particularly preferably comprises one or more compounds of the formulae IVb-1-1 and/or IVb-2-3.
  • R 1 and R 2 have the meanings indicated for R 2A above.
  • R 1 and R 2 preferably each, independently of one another, denote straight- chain alkyl or alkenyl.
  • Preferred LC media comprise one or more compounds of the formulae V- 1, V-3, V-4, V-6, V-7, V-10, V-11, V-12, V-14, V-15, and/or V-16 LC media according to the invention very particularly preferably comprise the compounds of the formula V-10, V-12, V-16 and/or IV-1, in particular in amounts of 5 to 30 %.
  • Preferred compounds of the formulae V-10 are indicated below:
  • the LC medium according to the invention particularly preferably com- prises the tricyclic compounds of the formula V-10a and/or of the formula V-10b in combination with one or more bicyclic compounds of the formulae IV-1
  • the total proportion of the compounds of the formulae V-10a and/or V- 10b in combination with one or more compounds selected from the bicyclohexyl compounds of the formula IV-1 is 5 to 40 %, very particularly preferably 15 to 35 %.
  • Very particularly preferred LC media comprise compounds V-10a and CC- 2-3
  • the compounds V-10a and IV-1-1 are preferably present in these LC media in a concentration of 15 to 35 %, particularly preferably 15 to 25 % and especially preferably 18 to 22 %, based on the mixture as a whole.
  • Further particularly preferred LC media comprise compounds V-10b and IV-1-1:
  • the compounds V-10b and IV-1-1 are preferably present in these LC media in a concentration of 15 to 35 %, particularly preferably 15 to 25 % and especially preferably 18 to 22 %, based on the mixture as a whole.
  • Further particularly preferred LC media comprise the following three com- pounds:
  • the compounds V-10a, V-10b and IV-1-1 are preferably present in these LC media in a concentration of 15 to 35 %, particularly preferably 15 to 25 % and especially preferably 18 to 22 %, based on the mixture as a whole.
  • Preferred LC media comprise at least one compound selected from the group consisting of the following formulae in which R 41 and R 42 , and R 51 and R 52 have the meanings indicated above.
  • R 41 and R 51 denotes alkyl or alkenyl having 1 to 6 or 2 to 6 C atoms, respectively, and R 42 and R 52 denotes alkenyl having 2 to 6 C atoms.
  • Preferred LC media comprise at least one compound of the formulae V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a and IV-3b: in which alkyl denotes an alkyl radical having 1 to 6 C atoms and alkenyl denotes an alkenyl radical having 2 to 6 C atoms.
  • the compounds of the formulae V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV- 3a and IV-3b are preferably present in the LC media according to the invention in amounts of 1 to 40 % by weight, preferably 5 to 35 % by weight and very particularly preferably 10 to 30 % by weight.
  • the LC medium additionally comprises one or more compounds selected from the group consisting of formulae VI-1 to VI-9
  • LC media comprising at least one compound of the formula V-9.
  • the LC medium additionally comprises one or more compounds selected from the group consisting of the formulae VII-1 to VII-25,
  • R denotes a straight-chain alkyl or alkoxy radical having 1 to 6 C atoms, (O) denotes -O- or a single bond, X denotes F, Cl, OCF 3 or OCHF 2 , L x denotes H or F, 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.
  • X preferably denotes F or OCH 3 , very preferably F.
  • the LC medium according to the invention preferably comprises the ter- phenyls of the formulae VII-1 to VII-25 in amounts of 2 to 30 % by weight, in particular 5 to 20 % by weight.
  • Particular preference is given to compounds of the formulae VII-1, VII-2, VII- 4, VII-20, VII-21, and VII-22 wherein X denotes F.
  • R preferably denotes alkyl, furthermore alkoxy, each having 1 to 5 C atoms.
  • R preferably denotes alkyl or alkenyl, in particular alkyl.
  • R preferably denotes alkyl.
  • X preferably denotes F.
  • terphenyls of formula VII-1 to VII-25 are preferably employed in the LC media according to the invention if the ⁇ n value of the mixture is to be ⁇ 0.1.
  • Preferred LC media comprise 2 to 20 % by weight of one or more terphenyl compounds selected from the group of the compounds of formulae VII-1 to VII-25. Further preferred embodiments are listed below: a) LC medium comprising at least one compound selected from the group consisting of formulae Z-1 to Z-14, in which R, (O) and “alkyl” have the meanings indicated above for formula III.
  • Preferred LC media comprise one or more compounds selected from the group of the difluorodibenzochroman compounds of the formula BC, chromans of the formula CR, and fluorinated phenanthrenes of the formulae PH-1 and PH-2, in which R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 each, independently of one another, have the meaning of R 2A .
  • c is 0, 1 or 2.
  • R 1 and R 2 preferably, independently of one another, denote alkyl or alkoxy having 1 to 6 C atoms.
  • the LC media according to the invention preferably comprise the compounds of the formulae BC, CR, PH-1, PH-2 in amounts of 3 to 20 % by weight, in particular in amounts of 3 to 15 % by weight.
  • Particularly preferred compounds of the formulae BC and CR are the compounds BC-1 to BC-7 and CR-1 to CR-5,
  • alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1 to 6 C atoms
  • alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2 to 6 C atoms.
  • LC media comprising one, two or three compounds of the formula BC-2, BF-1 and/or BF-2.
  • Preferred LC media comprise one or more indane compounds of the formula In, In in which R 11 , R 12 , 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 additionally denote halogen, preferably F, i denotes 0, 1 or 2.
  • Preferred compounds of the formula In are the compounds of the formulae In-1 to In-16 indicated below: Particular preference is given to the compounds of the formulae In-1, In-2, In-3 and In-4.
  • Preferred LC media additionally comprise one or more compounds of the formulae L-1 to L-5, in which R and R 1 each, independently of one another, have the meanings indicated for R 2A in formula IIA above, and alkyl denotes an alkyl radical having 1 to 6 C atoms.
  • the parameter s denotes 1 or 2.
  • Preferred LC media 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 IIA 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 subformulae
  • Alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms
  • 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 subformulae: in which Alkoxy and Alkoxy* have the meanings defined above and preferably denote methoxy, ethoxy, n- propyloxy, n-butyloxy or n- pentyloxy.
  • LC medium which additionally comprises one or more quaterphenyl compounds selected from the following formula: wherein R Q is alkyl, alkoxy, oxaalkyl or alkoxyalkyl having 1 to 9 C atoms or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated, X Q is F, Cl, halogenated alkyl or alkoxy having 1 to 6 C atoms or halogenated alkenyl or alkenyloxy having 2 to 6 C atoms, L Q1 to L Q6 independently of each other are H or F, with at least one of L Q1 to L Q6 being F.
  • R Q is alkyl, alkoxy, oxaalkyl or alkoxyalkyl having 1 to 9 C atoms or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated
  • X Q is F, Cl, halogenated alkyl or al
  • Preferred compounds of formula Q are those wherein R Q denotes straight-chain alkyl with 2 to 6 C-atoms, very preferably ethyl, n- propyl or n-butyl.
  • Preferred compounds of formula Q are those wherein L Q3 and L Q4 are F.
  • Further preferred compounds of formula Q are those wherein L Q3 , L Q4 and one or two of L Q1 and L Q2 are F.
  • Preferred compounds of formula Q are those wherein X Q denotes F or OCF 3 , very preferably F.
  • the compounds of formula Q are preferably selected from the following subformulae wherein R Q has one of the meanings of formula Q or one of its preferred meanings given above and below, and is preferably ethyl, n-propyl or n-butyl. Especially preferred are compounds of formula Q1, in particular those wherein R Q is n-propyl.
  • the proportion of compounds of formula Q in the LC host mixture is from >0 to ⁇ 5% by weight, very preferably from 0.05 to 2% by weight, more preferably from 0.1 to 1% by weight, most preferably from 0.1 to 0.8% by weight.
  • the LC medium contains 1 to 5, preferably 1 or 2 compounds of formula Q.
  • quaterphenyl compounds of formula Q to the LC host mixture enables to reduce ODF mura, whilst maintaining high UV absorption, enabling quick and complete polymerization, enabling strong and quick tilt angle generation, and increasing the UV stability of the LC medium.
  • compounds of formula Q which have positive dielectric anisotropy
  • the LC media according to the invention preferably comprise - one or more compounds of formula I or its subformulae, preferably in a total concentration in the range of from 0.001% to 0.02%, more preferably from 0.002% to 0.015%, most preferably from 0.005% to 0.015%, and/or - one or more compounds of formula IIA, preferably in a total concentration in the range of from 5% to 30%, more preferably from 7% to 25%, particularly preferably from 10% to 20%; and/or - one or more compounds of formulae IIA and IIB, preferably in a total concentration in the range of from 30% to 45%; and/or - one or more compounds of formula IV, preferably in a total concentration in the range of from 35% to 70%, more preferably from 40 % to 65%, particularly preferably from 45% to 60%; and/or - one or more compounds of formula IV-3, preferably in a total concentration in the range of from 35% to 60%, more preferably from 40 % to 55%, particularly preferably from 45% to
  • the medium comprises - one or more compounds CY-n-Om, in particular CY-3-O4, CY-5-O4 and/or CY-3-O2, preferably in a total concentration in the range of from 5% to 30%, preferably 10% to 20%; and/or - one or more compounds PY-n-Om, in particular PY-3-O2 and/or PY-1- O2, preferably in a total concentration in the range of from 5% to 30%, preferably 5% to 20%; and/or - CPY-n-Om, in particular CPY-2-O2, CPY-3-O2 and/or CPY-5-O2, pref- erably in concentrations > 5%, in particular 7% to 20%, based on the mixture as a whole, and/or - one or more compounds CCY-n-Om, preferably CCY-4-O2, CCY-3-O2, CCY-3-O3, CCY-3-O1 and/or CCY-5-O2, preferably in concentrations > 3%,
  • the compound of the formula CC-3-V1 in a total concentration in the range of from 5 to 40%, more preferably from 15% to 35%, particularly preferably from 20% to 30%, and/or - one or more compounds of formula B-nO-Om and/or B(S)-nO-Om, in particular the compound B(S)-2O-O4 and/or B(S)-2O-O5, preferably in a concentration in the range of from 2 to 12 %.
  • the invention furthermore relates to an electro-optical display having active-matrix addressing, characterised in that it contains, as dielectric, a liquid-crystalline medium according to claim 1 and wherein the display is a VA, SA-VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, PS-posi-VA, PS-TN, polymer stabilised SA-VA or polymer stabilised SA-FFS display.
  • active-matrix addressing characterised in that it contains, as dielectric, a liquid-crystalline medium according to claim 1 and wherein the display is a VA, SA-VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, PS-posi-VA, PS-TN, polymer stabilised SA-VA or polymer stabilised SA-FFS display.
  • the liquid-crystalline medium according to the invention preferably have a nematic phase from ⁇ -20°C to ⁇ 70°C, particularly preferably from ⁇ -30°C to ⁇ 80°C, very particularly preferably from ⁇ -40°C to ⁇ 90°C.
  • the medium according to the invention preferably has a clearing temperature of 70°C or more, very preferably of 74°C or more.
  • the LC medium has preferably a nematic LC phase.
  • the expression "have a nematic phase” here 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 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 stor- age 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 liquid-crystal mixture preferably has a nematic phase range of at least 60 K and a flow viscosity v 20 of at most 30 mm 2 ⁇ s -1 at 20°C.
  • the mixture is nematic at a temperature of -20°C or less, preferably at - 30°C or less, very preferably at -40°C or less.
  • the values of the birefringence ⁇ n in the liquid-crystal mixture are gener- ally between 0.07 and 0.16, preferably between 0.08 and 0.15, very preferably between 0.09 and 0.14.
  • the medium has a birefringence in the range of from 0.090 to 0.110, preferably from 0.095 to 0.105, in particular from 0.100 to 0.105.
  • the medium according to the invention has a birefringence of 0.120 or more, preferably in the range of from 0.125 to 0.145, more preferably from 0.130 to 0.140.
  • the liquid-crystal mixture according to the invention has a dielectric anisotropy ⁇ ⁇ of -1.5 to -8.0, preferably of -2.0 to – 4.0, in particular -2.5 to -3.5,
  • the rotational viscosity ⁇ 1 at 20°C is preferably ⁇ 120 mPa ⁇ s, in particular ⁇ 100 mPa ⁇ s.
  • the rotational viscosity ⁇ 1 at 20°C is ⁇ 100mPa ⁇ s, in particular ⁇ 95 mPa ⁇ s.
  • the liquid-crystal media according to the invention have relatively low val- ues for the threshold voltage (V 0 ).
  • the term "threshold voltage” relates to the capa- citive threshold (V 0 ), also called the Freedericks threshold, unless explicitly indicated otherwise.
  • the liquid-crystal media according to the invention have high values for the voltage holding ratio in liquid-crystal cells. In general, liquid-crystal media having a low addressing voltage or thresh- old 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 ⁇ ⁇ > 1.5
  • dielectrically neutral com- pounds denotes those having -1.5 ⁇ ⁇ ⁇ ⁇ 1.5
  • dielectrically negative compounds denotes those having ⁇ ⁇ ⁇ -1.5.
  • the dielectric ani- sotropy 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 ⁇ m 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. All temperature values indicated for the present invention are in °C.
  • the LC media according to the invention are suitable for all VA-TFT (vertical alignment-thin film transistor) applications, such as, for example, VAN (vertically aligned nematic), MVA (multidomain VA), (S)-PVA (super patterned VA), ASV (advanced super view, or axially symmetric VA), or UV 2 A. They are furthermore suitable for IPS (in-plane switching) and FFS (fringe field switching) applications having negative ⁇ ⁇ .
  • the nematic LC media in the displays according to the invention generally comprise two components NA and NB, which themselves consist of one or more individual compounds.
  • Component NA has significantly negative dielectric anisotropy and gives the nematic phase a dielectric anisotropy of ⁇ -0.5.
  • one or more compounds of the formula I it preferably comprises the compounds of the formulae IIA, IIB and/or IIC, furthermore one or more compounds of the formula IV-1.
  • the proportion of component NA is preferably between 45 and 100 %, in particular between 60 and 85 %.
  • component NA one (or more) individual compound(s) which has (have) a value of ⁇ ⁇ ⁇ -0.8 is (are) preferably selected.
  • Component NB has pronounced nematogeneity and a flow viscosity of not greater than 30 mm 2 ⁇ s -1 , preferably not greater than 25 mm 2 ⁇ s -1 , at 20°C.
  • Particularly preferred individual compounds in component NB are extremely low-viscosity nematic liquid crystals having a flow viscosity of not greater than 18 mm 2 ⁇ s -1 , preferably not greater than 12 mm 2 ⁇ s -1 , at 20°C.
  • Component NB is monotropically or enantiotropically nematic, has no smectic phases and is able to prevent the occurrence of smectic phases down to very low temperatures in LC media. For example, if various materials of high nematogeneity are added to a smectic liquid-crystal mix- ture, the nematogeneity of these materials can be compared through the degree of suppression of smectic phases that is achieved.
  • the mixture may optionally also comprise a component NC, comprising compounds having a dielectric anisotropy of ⁇ ⁇ ⁇ 1.5.
  • the medium preferably comprises 4 to 15, in particular 5 to 12, and particularly preferably ⁇ 10, compounds of the formulae IIA, IIB and/or IIC and optionally one or more compounds of the formula IV-1.
  • the other constituents are preferably selected from nematic or nemato- genic substances, in particular known substances, from the classes of the azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl cyclohexanecarboxylates, phenylcyclohexanes, cyclohexylbiphenyls, cyclohexylcyclohexanes, cyclo- hexylnaphthalenes, 1,4-biscyclohexylbiphenyls or cyclohexylpyrimidines, phenyl- or cyclohexyldioxanes, optionally halogenated stilbenes, benzyl phenyl ethers, tolanes and substituted cinnamic acid esters.
  • R 20 and R 21 are different from one another, one of these radicals usually being an alkyl or alkoxy group.
  • Other variants of the proposed substituents are also common. Many such substances or also mixtures thereof are commercially available. All these substances can be prepared by methods known from the literature. It goes without saying for the person skilled in the art that the 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 corres- ponding isotopes.
  • the combination of compounds of the preferred embodiments mentioned above with the polymerized compounds described above causes low threshold voltages, low rotational viscosities and very good low-tem- perature stabilities in the LC media according to the invention at the same time as constantly high clearing points and high HR values, and allows the rapid establishment of a particularly low tilt angle (i.e. a large tilt) in PSA displays.
  • the LC media exhibit significantly shortened response times, in particular also the grey-shade response times, in PSA displays compared with the LC media from the prior art.
  • the invention furthermore relates to an LC display comprising an LC medium as described above and below.
  • the LC display is preferably a VA, IPS, FFS, UB-FFS or UV 2 A display.
  • the structure of the 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 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 as described above and below.
  • 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.
  • UV 2 A displays the alignment layer is made by photopolymerization using linear polarized UV light and irradiation at an oblique angle.
  • 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 LC 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 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 the LC medium may also comprise, in addition to the compounds of formula I, one or more further stabilizers. Suitable types and amounts of stabilizers are known to the person skilled in the art and are described in the literature.
  • the LC media contain one or more chiral dopants, preferably in a concentration from 0.01 to 1% by weight, very preferably from 0.05 to 1.0% by weight.
  • the chiral dopants are preferably selected from the group consisting of compounds from Table B below, very preferably from the group consisting of R- or S-1011, R- or S-2011, R- or S-3011, R- or S-4011, and R- or S-5011.
  • the LC media contain a racemate of one or more chiral dopants, which are preferably selected from the chiral dopants mentioned in the previous paragraph.
  • a racemate of one or more chiral dopants which are preferably selected from the chiral dopants mentioned in the previous paragraph.
  • it is possible to add to the LC media for example, 0 to 15% by weight of pleochroic dyes, furthermore nanoparticles, conductive salts, preferably ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutyl- ammonium tetraphenylborate or complex salts of crown ethers (cf., for example, Haller et al., Mol. Cryst. Liq.
  • Corresponding compounds of the formula ZK are described, for example, in DE-A- 2636 684 and DE-A-3321373.
  • the LC media which can be used in accordance with the invention are prepared in a manner conventional per se, for example by mixing one or more of the above-mentioned compounds with one or more compounds of formula I as defined above, and optionally with further liquid-crystalline compounds and/or additives.
  • the desired amount of the com- ponents used in lesser amount is dissolved in the components making up the principal constituent, advantageously at elevated temperature. It is also possible to mix solutions of the components in an organic solvent, for example in acetone, chloroform or methanol, and to remove the solvent again, for example by distillation, after thorough mixing.
  • the invention furthermore relates to the process for the preparation of the LC media according to the invention.
  • the LC media according to the invention may also comprise compounds in which, for example, H, N, O, Cl, F have been replaced by the corresponding isotopes like deuterium etc.
  • the following examples explain the present invention without restricting it. However, they show the person skilled in the art preferred mixture con- cepts with compounds preferably to be employed and the respective con- centrations thereof and combinations thereof with one another. In addition, the examples illustrate which properties and property combinations are accessible. Preferred mixture components are shown in Table A below.
  • m and n are independently of each other an integer from 1 to 12, preferably 1, 2, 3, 4, 5 or 6, k is 0, 1, 2, 3, 4, 5 or 6, and (O)C m H 2m+1 means C m H 2m+1 or OC m H 2m+1 .
  • the LC media according to the invention comprise one or more compounds selected from the group consisting of compounds from Table A.
  • Table B shows possible chiral dopants which can be added to the LC media according to the invention.
  • the LC media preferably comprise 0 to 10% by weight, in particular 0.01 to 5% by weight, particularly preferably 0.1 to 3% by weight, of dopants.
  • the LC media preferably comprise one or more dopants selected from the group consisting of compounds from Table B.
  • Table C Table C shows possible stabilizers which can be added to the LC media according to the invention.
  • n denotes an integer from 1 to 12, preferably 1, 2, 3, 4, 5, 6, 7 or 8, and terminal methyl groups are not shown.
  • the LC media preferably comprise 0 to 10% by weight, in particular 1 ppm to 5% by weight, particularly preferably 1 ppm to 1% by weight, of stabilizers.
  • the LC media preferably comprise one or more stabilizers selected from the group consisting of compounds from Table C. Examples The following examples explain the present invention without restricting it. However, they show the person skilled in the art preferred mixture con- cepts with compounds preferably to be employed and the respective con- centrations thereof and combinations thereof with one another. In addition, the examples illustrate which properties and property combinations are accessible.
  • threshold voltage for the present invention relates to the capa- citive threshold (V 0 ), also known as the Freedericks threshold, unless explicitly indicated otherwise.
  • the optical threshold may also, as generally usual, be quoted for 10% relative contrast (V 10 ).
  • nematic LC host mixture N1 is formulated as follows Stabilised mixture S1.1 is prepared by adding 100ppm of the compound M1 according to formula I to the nematic LC host mixture N1. Stabilised mixture S1.2 is prepared by adding 200ppm of the compound M1 according to formula I to the nematic LC host mixture N1.
  • the mixture C1 is prepared by adding 300ppm of the compound M1 to the nematic LC host mixture N1.
  • Example 2 The nematic LC host mixture N2 is formulated as follows Stabilised mixture S2 is prepared by adding 150ppm of the compound M1 to the nematic LC host mixture N2.
  • Example 3 The nematic LC host mixture N3 is formulated as follows
  • Stabilised mixture S3 is prepared by adding 100ppm of the compound M1 to the nematic LC host mixture N3.
  • Example 4 The nematic LC host mixture N4 is formulated as follows Stabilised mixture S4.1 is prepared by adding 100ppm of the compound M1 to the nematic LC host mixture N4.
  • Stabilised mixture S4.2 is prepared by adding 200ppm of the compound M1 to the nematic LC host mixture N4.
  • Example 5 The nematic LC host mixture N5 is formulated as follows
  • Stabilised mixture S5 is prepared by adding 100ppm of the compound M1 to the nematic LC host mixture N5.
  • Example 6 The nematic LC host mixture N6 is formulated as follows Stabilised mixture S6 is prepared by adding 150ppm of the compound M1 to the nematic LC host mixture N6.
  • Example 7 The nematic LC host mixture N7 is formulated as follows
  • Stabilised mixture S7 is prepared by adding 100ppm of the compound M1 to the nematic LC host mixture N7.
  • Example 8 The nematic LC host mixture N8 is formulated as follows Stabilised mixture S8 is prepared by adding 150ppm of the compound M1 to the nematic LC host mixture N8.
  • Example 9 The nematic LC host mixture N9 is formulated as follows
  • Stabilised mixture S9 is prepared by adding 150ppm of the compound M1 to the nematic LC host mixture N9.
  • Example 10 The nematic LC host mixture N10 is formulated as follows Stabilised mixture S10.1 is prepared by adding 100ppm of the compound M1 to the nematic LC host mixture N10.
  • Stabilised mixture S10.2 is prepared by adding 200ppm of the compound M1 to the nematic LC host mixture N10.
  • Example 11 The nematic LC host mixture N11 is formulated as follows
  • Stabilised mixture S11 is prepared by adding 100ppm of the compound M1 to the nematic LC host mixture N11.
  • VHR of stabilised mixtures S1.1 and S1.2 according to the present invention containing the compound M1 is measured compared to the pure host mixture N1.
  • VHR Measurement The test cells used for VHR measurement consist of two plane-parallel glass outer plates at a separation of 3.2 ⁇ m, each of which has on the inside an electrode layer and a polyimide alignment layer on top, where the two polyimide layers effect homeotropic alignment of the liquid crystal molecules and photoalignment is applied to induce tilt directions at the two substrates crossed to one another. Six test cells are prepared for each LC mixture. After filling in the LC mixtures the cells are sealed by a sealent.
  • VHR of host mixture N1 and mixtures S1.1 and S1.2 is measured at 60°C with application of a voltage of 1 V / 0.6 Hz before and after 120 hours of BL stress at 60°C.
  • Light and thermal stress usually causes the generation of impurity and ion which decrease of VHR in LC mixtures, therefore the smaller the absolute decrease of VHR value after stress, the better the performance for display applications.
  • Table 1 - VHR From Table 1 it can be seen that for mixtures S1.1 and S1.2 according to the present invention the initial VHR is already higher than the initial VHR of host mixture N1 without the compound M1.
  • the tilt angle generation of stabilised mixture S1.1 according to the present invention is measured compared to the pure host mixture N1 and to comparison mixture C1 with a higher amount of compound M1.
  • the test cells used for tilt angle measurement consist of two plane-parallel glass outer plates at a separation of 3.2 ⁇ m, each of which has on the inside an electrode layer and a polyimide alignment layer on top, where the two polyimide layers effect homeotropic alignment of the liquid crystal molecules and photoalignment is applied to induce tilt directions at the two substrates anti-parallel to one another.
  • the LC mixtues are filled into the text cells which are then sealed by a sealent.
  • the tilt angle generated in host mixture N1 and mixtures S1.1 and C1 is measured before and after exposure to BL and electric stress of 60 Vpp for 120h using the Mueller Matrix Polarimeter “AxoScan” from Axometrics.
  • the tilt angle variation i.e. the change of the tilt angle ⁇ tilt in absolute values after stress is shown in Table 2 below.
  • Table 2 – Tilt Variation From Table 2 it can be seen that mixture S1.1 according to the present invention with 100ppm of compound M1 shows a small tilt angle change which is similar to host mixture N1, which means that no significant tilt angle has been generated by the compound M1 at this concentration.
  • comparison mixture C1 with 300ppm of compound M1 shows a stronger tilt angle change indicating that a tilt angle has been generated.

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  • Organic Chemistry (AREA)
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Abstract

La présente invention concerne un milieu à cristaux liquides (CL) comprenant un stabilisant, son utilisation à des fins optiques, électro-optiques et électroniques, en particulier dans des afficheurs à CL, en particulier dans des afficheurs à CL du mode aligné verticalement, un afficheur à CL du mode aligné verticalement comprenant le milieu à CL, et un procédé de fabrication de l'afficheur à CL.
PCT/EP2022/054906 2021-03-02 2022-02-28 Milieu à cristaux liquides WO2022184604A1 (fr)

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