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WO2018153803A1 - Milieu cristallin liquide et écran à cristaux liquides comportant ledit milieu - Google Patents

Milieu cristallin liquide et écran à cristaux liquides comportant ledit milieu Download PDF

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Publication number
WO2018153803A1
WO2018153803A1 PCT/EP2018/053988 EP2018053988W WO2018153803A1 WO 2018153803 A1 WO2018153803 A1 WO 2018153803A1 EP 2018053988 W EP2018053988 W EP 2018053988W WO 2018153803 A1 WO2018153803 A1 WO 2018153803A1
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atoms
compounds
liquid
alkyl
formula
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PCT/EP2018/053988
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English (en)
Inventor
Hyun-Jin Yoon
Ji-Won Jeong
Eun-Kyu Lee
Chang-Suk Choi
Min-Ok Jin
Yong-Kuk Yun
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Merck Patent Gmbh
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Priority to KR1020197027081A priority Critical patent/KR20190121791A/ko
Priority to CN201880012776.1A priority patent/CN110325620A/zh
Publication of WO2018153803A1 publication Critical patent/WO2018153803A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • 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
    • C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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-)
    • C09K2019/123—Ph-Ph-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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)
    • C09K2019/301—Cy-Cy-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring

Definitions

  • Liquid-crystalline medium and liquid-crystal display comprising the same
  • the present invention relates to a liquid-crystalline medium (LC medium) comprising a polymerizable piperidine derivative as an additive for stabilization, to the use thereof for electro-optical purposes, and to LC displays containing this medium, particularly to liquid-crystal displays which use the IPS (in-Djane switching) or the FFS (fringe field switching) effect using dielectrically positive liquid crystals.
  • LC medium liquid-crystalline medium
  • IPS in-Djane switching
  • FFS far field switching
  • Liquid crystals are used principally as dielectrics in display devices, since the optical properties of such substances can be modified by an applied voltage. Electro-optical devices based on liquid crystals are extremely well known to the person skilled in the art and can be based on various effects. Examples of such devices are cells having dynamic scattering, DAP
  • TN cells having a "twisted nematic” structure
  • STN super-twisted nematic
  • SBE superbirefringence effect
  • OMI optical mode interference
  • the commonest display devices are based on the Schadt-Helfrich effect and have a twisted nematic structure.
  • IPS in-plane switching
  • TN, STN, FFS (fringe field switching) and IPS cells are currently commercially interesting areas of application for the media according to the invention.
  • the liquid-crystal materials must have good chemical and thermal stability and good stability to electric fields and electromagnetic radiation. Furthermore, the liquid-crystal materials should have low viscosity and produce short addressing times, low threshold voltages and high contrast in the cells.
  • a suitable mesophase for example a nematic or cholesteric mesophase for the above-mentioned cells, at the usual operating temperatures, i.e. in the broadest possible range above and below room temperature.
  • liquid crystals are generally used as mixtures of a plurality of components, it is important that the components are readily miscible with one another.
  • Further properties, such as the electrical conductivity, the dielectric anisotropy and the optical anisotropy have to satisfy various requirements depending on the cell type and area of application. For example, materials for cells having a twisted nematic structure should have positive dielectric anisotropy and low electrical conductivity.
  • Matrix liquid-crystal displays with integrated non-linear elements for switching individual pixels (MLC displays)
  • MLC displays media having large positive dielectric anisotropy, broad nematic phases, relatively low birefringence, very high specific resistance, good UV and temperature stability and low vapour pressure are desired.
  • Matrix liquid-crystal displays of this type are known.
  • nonlinear elements which can be used to individually switch the individual pixels are active elements (i.e. transistors).
  • active matrix is then used, where a distinction can be made between two types: 1 .
  • MOS metal oxide semiconductor
  • other diodes on silicon wafers as substrate.
  • TFTs Thin-film transistors (TFTs) on a glass plate as substrate.
  • TFTs Thin-film transistors
  • substrate material restricts the display size, since even modular assembly of various part-displays results in problems at the joints.
  • the electro- optical effect used is usually the TN effect.
  • TFTs comprising compound semiconductors, such as, for example, CdSe, or TFTs based on polycrystalline or amorphous silicon. Intensive work is being carried out worldwide on the latter technology.
  • the TFT matrix is applied to the inside of one glass plate of the display, while the other glass plate carries the transparent counterelectrode on its inside. Compared with the size of the pixel electrode, the TFT is very small and has virtually no adverse effect on the image.
  • This technology can also be extended to fully colour-capable displays, in which a mosaic of red, green and blue filters is arranged in such a way that a filter element is opposite each switchable pixel.
  • the TFT displays usually operate as TN cells with crossed polarisers in transmission and are backlit.
  • MLC displays of this type are particularly suitable for TV applications (for example pocket televisions) or for high-information displays for computer applications (laptops) and in automobile or aircraft construction.
  • TV applications for example pocket televisions
  • high-information displays for computer applications (laptops) and in automobile or aircraft construction.
  • difficulties also arise in MLC displays due to insufficiently high specific resistance of the liquid-crystal mixtures [TOGASHI, S., SEKI- GUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210- 288 Matrix LCD Controlled by Double Stage Diode Rings, pp.
  • liquid-crystal displays which use backlighting, i.e. are operated transmissively and if desired transflectively
  • reflective liquid-crystal displays are also particularly interesting. These reflective liquid-crystal displays use the ambient light for information display. They thus consume significantly less energy than backlit liquid-crystal displays having a corresponding size and resolution. Since the TN effect is characterised by very good contrast, reflective displays of this type can even be read well in bright ambient conditions. This is already known of simple reflective TN displays, as used, for example, in watches and pocket calculators. However, the principle can also be applied to high-quality, higher-resolution active matrix-addressed displays, such as, for example, TFT displays.
  • liquid crystals of low birefringence are necessary in order to achieve low optical retardation (d ⁇ ⁇ ).
  • This low optical retardation results in usually acceptably low viewing-angle dependence of the contrast (cf. DE 30 22 818).
  • the use of liquid crystals of low birefringence is even more important than in transmissive displays since the effective layer thickness through which the light passes is approximately twice as large in reflective displays as in transmissive displays having the same layer thickness.
  • displays having fast response times are required in order to be able to reproduce multimedia content, such as, for example, films and video games, in near-realistic quality.
  • Such short response times can be achieved, in particular, if liquid-crystal media having low values for the viscosity, in particular the rotational viscosity ⁇ , and having high optical anisotropy ( ⁇ ) are used.
  • Electro- optical lens systems by means of which a 2-dimensional representation of a display can be converted into a 3-dimensional autostereoscopic representation can be achieved using mixtures having high optical anisotropy ( ⁇ ).
  • TN Schot-Helfrich
  • media are desired which facilitate the following advantages in the cells: extended nematic phase range (in particular down to low temperatures) the ability to switch at extremely low temperatures (outdoor use, automobiles, avionics) increased resistance to UV radiation (longer lifetime) low threshold voltage.
  • the physical parameters which essentially determine the response time of a liquid-crystal mixture are the rotational viscosity ⁇ - ⁇ and the elastic constants. The latter are also particularly important for ensuring a good black state of the LCD. In general, however, it is observed that the clearing point of the mixture and thus the rotational viscosity of the mixture is also increased with an increase in the elastic constants, meaning that an improvement in the response time is not possible.
  • LC displays for TV and video applications for example LCD TVs, monitors, PDAs, notebooks, games consoles
  • a reduction in the layer thickness d ("cell gap") of the LC medium in the LC cell theoretically results in faster response times, but requires LC media having higher birefringence ⁇ in order to ensure an adequate optical retardation (d ⁇ ).
  • the LC materials of high birefringence known from the prior art generally also have high rotational viscosity at the same time, which in turn has an adverse effect on the response times.
  • liquid-crystalline media having good reliability properties, such as, for example, high VHR (voltage holding ratio), which do not exhibit these properties or only do so to a lesser extent.
  • the invention is based on the object of providing media, in particular for
  • the LC media should have fast response times and low rotational viscosities at the same time as relatively high birefringence.
  • the LC media should have a high clearing point and very good low-temperature stability (LTS).
  • the IPS or the FFS effect with dielectrically positive liquid crystalline media in a homogeneous alignment are preferred.
  • Liquid crystalline media having a positive dielectric anisotropy for IPS and FFS displays have already been disclosed. In the following some examples will be given.
  • WO 2012/079676 A1 discloses liquid crystalline media with highly positive dielectric anisotropy.
  • the publication WO 2013/182271 A1 discloses liquid crystalline media with a positive dielectric anisotropy, which is additionally stabilized by Tinuvin 770®.
  • Polymerizable piperidine derivatives as disclosed herein have been proposed as additives in polymerizable liquid crystalline media in WO 2016/1 161 19 A1 .
  • liquid-crystal displays which have, in particular in IPS and FFS displays, a low threshold voltage with short response times, a sufficiently broad nematic phase, favourable birefringence ( ⁇ ) and, at the same time, a high transmission, good stability to decomposition by heating and by UV exposure, and a stable, high VHR if use is made of nematic liquid-crystal mixtures which comprise at least one compound of formula I as below, or a polymer comprising its polymerized form,
  • Ch -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, CI or P-Sp-, or a group T,
  • Ch - groups having 1 to 25 C atoms, wherein one or more non-adjacent Ch - 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, CI or P-Sp-, or a group selected from formula 1 , 2 and 3, ml 0, 1 , 2, 3 or 4, m2 0, 1 , 2, 3 or 4, and n 1 , 2, 3 or 4.
  • the invention relates to a liquid-crystalline medium having a nematic phase and a dielectric anisotropy ( ⁇ ) of 1 .5 or more, characterised in that it comprises one or more compounds of the formula I as described above and below or comprises a polymer comprising one or more compounds of the formula I polymerized form.
  • the invention more specifically relates to an liquid-crystalline medium comprising
  • LC host mixture comprising, preferably consisting of, one or more mesogenic or liquid-crystalline compounds.
  • the liquid-crystalline component B) of an liquid-crystalline medium according to the present invention is hereinafter also referred to as "LC host mixture”, and preferably comprises one or more, preferably at least two mesogenic or LC compounds selected from low-molecular-weight compounds which are unpolymerisable.
  • the invention furthermore relates to an liquid-crystalline medium as described above and below, wherein the LC host mixture or component B) comprises at least one mesogenic or LC compound comprising an alkenyl group.
  • the invention furthermore relates to an liquid-crystalline medium or LC display as described above and below, wherein the compounds of formula I, or the polymerisable compounds of component A), are polymerised.
  • the invention furthermore relates to a process for preparing an liquid- crystalline medium as described above and below, comprising the steps of mixing one or more mesogenic or LC compounds, or an LC host mixture or LC component B) as described above and below, with one or more compounds of formula I, and optionally with further LC compounds and/or additives.
  • Media of this type can be used, in particular, for electro-optical displays having active-matrix addressing for IPS - or FFS displays.
  • the media according to the present invention preferably additionally comprise a one or more compounds selected from the group of
  • the mixtures according to the invention exhibit very broad nematic phase ranges with clearing points > 70°C, relatively high values for the voltage holding ratio (VHR) , very favourable values for the capacitive threshold and at the same time good low-temperature stabilities at -20°C and -30°C, as well as very low rotational viscosities.
  • the mixtures according to the invention are furthermore distinguished by a good ratio of clearing point and rotational viscosity and by a relatively high positive dielectric anisotropy. Remarkably, the reliability of the mixtures is improved. Little image burning is observed.
  • the voltage holding ratio is high even after extended use or, similarly after standard ageing tests like accelerated light load, heat or UV test.
  • the liquid-crystalline media according to the present invention on the one hand, have a value of the dielectric anisotropy of 2 or more, preferably of 3.5 or more preferably of 4.5 or more. At the other hand, they preferably have a dielectric anisotropy of 25 or less.
  • the liquid crystalline media according to the present invention in a preferred embodiment have a positive dielectric anisotropy, preferably in the range from 2.0 or more to 25 or less, more preferably in the range from 3.0 or more to 22 or less and, most preferably in the range from 8.0 or more to 20 or less.
  • the compounds of formula I are preferably employed in the liquid crystalline media in a concentration in the range from 0.0005 % by weight to 2 %, more preferably in the range from 0.001 % to 1 %, particularly preferably in the range from 0.005 % to 0.05 %, all % by weight.
  • the total content of polymerizable or polymerized components in the liquid crystalline medium according to the invention is preferably below 0.1 % by weight, more preferably below 0.05 %, and most preferably lower than 0.02 % (200 ppm).
  • the liquid crystalline medium preferably comprises a) one or more compounds of formula I, one or more dielectrically positive compounds selected from the group of compounds of formulae II and III, preferably of compounds having a dielectric anisotropy of greater than 3 each:
  • alkoxy having 1 to 7 C atoms
  • alkenyl alkenyloxy, alkoxyalkyi or fluorinated alkenyl having 2 to 7 C atoms and preferably alkyl or alkenyl, on each appearance, independently of one another, denote
  • L 31 and L 32 independently of one another, denote H or F, preferably L 31 denotes F,
  • X 3 denotes halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, F, CI, -OCF 3 , -OCHF 2 ,
  • R 41 and R 42 independently of one another, have the meaning indicated above for R 2 under formula II, preferably R 41 denotes alkyl and R 42 denotes alkyl or alkoxy or R 41 denotes alkenyl and R 42 denotes alkyl,
  • a 41 occurs twice, also these independently of one another, denote
  • CF CF-, -CH2O-, -CF2O-, -C ⁇ C- or a single bond, preferably one or more thereof denotes/denote a single bond, and p denotes 0, 1 or 2, preferably 0 or 1 , and
  • R 51 and R 52 independently of one another, have one of the meanings given for R 41 and R 42 and preferably denote alkyl having 1 to 7 C atoms, preferably n-alkyl, particularly preferably n- alkyl having 1 to 5 C atoms, alkoxy having 1 to 7 C atoms, preferably n-alkoxy, particularly preferably n-alkoxy having
  • Z 51 to Z 53 each, independently of one another, denote -CH2-CH2-
  • -CH2-O-, -CH CH-, -C ⁇ C-, -COO- or a single bond, preferably -CH2-CH2-, -CH2-O- or a single bond and particularly preferably a single bond, i and j each, independently of one another, denote 0 or 1 , preferably denotes 0, 1 or 2, more preferably 0 or 1 and, most preferably, 1 .
  • the liquid-crystalline media in accordance with the present application preferably have a nematic phase.
  • R 1 alkyl means an alkyl group, which may be straight-chain or branched. Each of these radicals is preferably straight-chain and preferably has 1 , 2, 3, 4, 5, 6, 7 or 8 C atoms and is accordingly preferably methyl, ethyl, n-propyl, n- butyl, n-pentyl, n-hexyl or n-heptyl.
  • chiral groups are 2-alkyl, 2-alkoxy, 2-methylalkyl, 2-methylalkoxy, 2- fluoroalkyi, 2-fluoroalkoxy, 2-(2-ethin)-alkyl, 2-(2-ethin)-alkoxy, 1 ,1 ,1 -trifluoro-2- alkyl and 1 ,1 ,1 -trifluoro-2-alkoxy.
  • the compounds of formula I are prepared according to WO 2016/1 161 19 A1 or are commercially available.
  • the invention furthermore relates to the use of liquid-crystal mixtures and liquid-crystalline media according to the invention in IPS and FFS displays, in particular the use in IPS displays containing a liquid-crystalline medium, for improving the voltage-holding-ratio.
  • the invention furthermore relates to a liquid-crystal display containing a liquid-crystalline medium according to the invention, in particular an IPS or FFS display, particularly preferably a IPS display.
  • a liquid-crystal display containing a liquid-crystalline medium according to the invention, in particular an IPS or FFS display, particularly preferably a IPS display.
  • the displays in accordance with the present invention are preferably addressed by an active matrix (active matrix LCDs, AMDs for short), preferably by a matrix of thin-film transistors (TFTs).
  • TFTs thin-film transistors
  • the liquid crystals according to the invention can also be used in an advantageous manner in displays having other known addressing means.
  • the invention furthermore relates to a process for the preparation of a liquid-crystalline medium according to the invention by mixing one or more compounds of formula I with one or more low-molecular-weight liquid- crystalline compounds, or a liquid-crystal mixture and optionally with further liquid-crystalline compounds and/or additives, resulting in a liquid crystalline medium having a nematic phase and a dielectric anisotropy ( ⁇ ) of 1 .5 or more.
  • 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”.
  • halogen refers to fluorine, chlorine or bromine, preferably fluorine or chlorine and in particular to fluorine.
  • halogenated is used analogously.
  • 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 is known to the person skilled in the art and is described in the literature, and denotes a group which, due to the ani- sotropy of its attracting and repelling interactions, essentially contributes to causing a liquid-crystalline (LC) phase in low-molecular-weight or polymeric substances.
  • Compounds containing mesogenic groups do not necessarily have to have a liquid-crystalline phase themselves. It is also possible for mesogenic compounds to exhibit liquid- crystalline phase behaviour only after mixing with other compounds and/or after polymerisation. Typical mesogenic groups are, for example, rigid rod- or disc-shaped units.
  • spacer group or "spacer” for short, also referred to as “Sp” above and below, is known to the person skilled in the art and is described in the literature, see, for example, Pure Appl. Chem. 73(5), 888 (2001 ) and C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 1 16, 6340-6368.
  • spacer group or “spacer” above and below denotes a flexible group which connects the mesogenic group and the polymerisable group(s) to one another in a polymerisable mesogenic compound. Whereas the mesogenic group generally contains rings, the spacer group is generally without ring systems, i.e. is in chain form, where the chain may also be branched. The term chain is applied, for example, to an alkylene group. Substitutions on and in the chain, for example by - O- or -COO-, are generally included.
  • the spacer (the spacer group) is a linker between functional structural parts of a molecule which facilitates a certain spatial flexibility between these parts.
  • liquid-crystalline medium is intended to denote a medium which comprises a liquid-crystal mixture and one or more polymerisable compounds (such as, for example, of formula I or reactive mesogens).
  • liquid-crystal mixture (or “host mixture) is intended to denote a liquid-crystalline mixture which consists exclusively of unpolymerisable, low-molecular-weight compounds, preferably of two or more liquid-crystalline compounds and optionally further additives, such as, for example, chiral dopants or stabilisers.
  • liquid-crystal mixtures and liquid-crystalline media which have a nematic phase, in particular at room temperature.
  • ml in formula I is 0 or 1 , most preferably 0.
  • pa, b, c, d are independently straight chain or branched alkyl with 1 to 10 C atoms.
  • Z 1 in formula I denotes -CO-O-, -O-CO- or a single bond, very preferably -CO-O- or a single bond.
  • Z 2 and Z 3 in formula I denote -CO-O-, -O-CO- or a single bond, very preferably a single bond.
  • P in formula I is an acrylate or methacrylate group.
  • Sp in formula I is a single bond
  • a 3 in formula I denotes an aromatic or heteroaromatic group with 6 to 24 ring atoms, which may also contain fused rings, and is optionally substituted by one or more groups L.
  • a 3 in formula I denotes benzene or naphthalene, which optionally substituted by one or more groups L.
  • a 1 and A 2 in formula I denote an aromatic or heteroaromatic group with 6 to 24 ring atoms, which may also contain fused rings, and is optionally substituted by one or more groups L or R-(A 3 -Z 3 ) m 2-, or A 1 is a single bond.
  • a 1 and A 2 in formula I denote benzene, cyclohexylene, naphthalene, phenanthrene or anthracene, which is optionally substituted by one or more groups L or R-(A 3 -Z 3 ) m 2-, or A 1 is a single bond.
  • -(A 2 -Z 2 -A 1 ) m i- in formula I denotes benzene, biphenylene, p- terphenylene (1 ,4-diphenylbenzene), m-terphenylene (1 ,3- diphenylbenzene), naphthylene, 2-phenyl-naphthylene, phenanthrene or anthracene, all of which are optionally substituted by one or more groups L.
  • -(A 2 -Z 2 -A 1 ) m i- denotes biphenylene, p-terphenylene or m- terphenylene, all of which are optionally substituted by one or more groups L.
  • Preferred groups -(A 2 -Z 2 -A 1 ) m i- are selected from the following formulae
  • L is as defined in formula I or has one of the preferred meanings as described above and below, r is 0, 1 , 2, 3 or 4, s is 0, 1 , 2 or 3, t is 0, 1 or 2, and u is 0, 1 , 2, 3, 4 or 5.
  • Preferred compounds of formula I are selected from the following subformulae
  • R e is alkyl having 1 to 12 C atoms
  • r is 0, 1 , 2, 3 or 4 and
  • Z 1 in formulae I and 1-1 to I-45 is -CO-O-, -O-CO-, or a single bond, very preferably -CO-O- or a single bond.
  • P in formulae I and 1-1 to I-45 is acrylate or methacrylate.
  • Sp in formulae I and 1-1 to I-45 is a single bond.
  • R a , R b , R c and R d in formulae I and 1-1 to I-45 are methyl.
  • R g in formula I is H
  • Preferred structures among 1-1 to I-45 are the structures 1-1 and I-23, particularly structure I-23.
  • the compounds contain exactly one polymerisable group
  • - P is acrylate or methacrylate
  • Sp when being different from a single bond, is selected from
  • R a , R b , R c and R d are methyl
  • R e is methyl, ethyl, n-propyl, iso-propyl, tert-butyl, n-butyl or n-pentyl,
  • n 0, 1 or 2
  • n2 0, 1 or 2
  • Z 1 denotes -CO-O-, -O-CO- or a single bond, preferably -CO-O-
  • - Z 2 denotes -CO-O-, -O-CO- or a single bond, preferably a single bond
  • L denotes F, CI, CN, or alkyl or alkoxy with 1 to 6 C atoms that is optionally fluorinated, very preferably F, CI, CN, Chb, OCH3, OCF3, OCF 2 H or OCFH 2 , most preferably F,
  • one or more of L denote a group T
  • r is 0 or 1 ,
  • the liquid-crystal medium comprises one or more dielectrically positive compounds having dielectric anisotropy of greater than 3, selected from the group of the com pounds of the formulae 11-1 and II-2:
  • n which the parameters have the respective meanings indicated above under formula II, and L 23 and L 24 , independently of one another, denote H or F, preferably L 23 denotes F, and
  • X 2 preferably denotes F or OCF3, particularly preferably F, and, in the case of formula II-2,
  • the media in accordance with the present invention may comprise, alternatively or in addition to the compounds of the formulae 111-1 and/or III-2, one or more compounds of the formula III-3
  • the liquid-crystal medium preferably comprises compounds selected from the group of the compounds of the formulae 11-1 and II-2 in which L 21 and L 22 and/or L 23 and L 24 both denote F.
  • the liquid-crystal medium comprises compounds selected from the group of the compounds of the formulae 11-1 and II-2 in which L 21 , L 22 , L 23 and L 24 all denote F.
  • the liquid-crystal medium preferably comprises one or more compounds of the formula 11-1 .
  • the compounds of the formula 11-1 are preferably selected from the group of the compounds of the formulae 11-1 a to 11-1 e, preferably one or more compounds of formulaell-1 a and/or 11-1 b and/or II- 1 d, preferably of formula 11-1 a and/or 11-1 d or 11-1 b and/or 11-1 d, most preferably of formula 11-1 d:
  • L 21 and L 22 both denote F and/or L 23 and L 24 both denote F, and in formula 11-1 e,
  • L 21 , L 22 and L 23 denote F.
  • the liquid-crystal medium preferably comprises one or more compounds of the formula II-2, which are preferably selected from the group of the compounds of the formulae ll-2a to ll-2k, preferably one or more compounds each of formulae ll-2a, ll-2h, ll-2k and/or ll-2j:
  • L 25 to L 28 independently of one another, denote H or F, preferably L 27 and L 28 both denote H, particularly preferably L 26 denotes H.
  • the liquid-crystal medium preferably comprises compounds selected from the group of the compounds of the formulae ll-2a to ll-2k in which L 21 and L 22 both denote F and/or L 23 and L 24 both denote F.
  • the liquid-crystal medium comprises compounds selected from the group of the compounds of the formulae ll-2a to ll-2k in which L 21 , L 22 , L 23 and L 24 all denote F.
  • Especially preferred compounds of the formula 11-2 are the compounds of the following formulae, particularly preferred of formulae ll-2a-1 , ll-2h-1 and/or ll-2k-1 and/or ll-2j-1 :
  • the liquid-crystal medium preferably comprises one or more compounds of the formula 111-1 .
  • the compounds of the formula 111-1 are preferably selected from the group of the compounds of the formulae lll-1 a to lll-1j, preferably from formulae 111-1 c, 111-1 f, 111-1 g and 111-1 k:
  • the parameters L 33 and L 34 independently of one another and of the other parameters, denote H or F and the parameters L 35 and L 36 , independently of one another and of the other parameters, denote H or F.
  • the liquid-crystal medium preferably comprises one or more compounds of the formula lll-1 c, which are preferably selected from the group of the compounds of the formulae lll-1 c-1 to lll-1 c-5, preferably of formulae III- 1 c-1 and/or lll-1 c-2, most preferably of formula 111 - 1 c- 1 :
  • the liquid-crystal medium preferably comprises one or more compounds of the formula lll-1f, which are preferably selected from the group of the compounds of the formulae lll-1f-1 to lll-1f-6, preferably of formulae III-1M and/or lll-1f-2 and/or lll-1f-3 and /or IIMf-6, more preferably of formula lll-1f-3 and/or lll-1f-6, more preferably of formula lll-1f-6:
  • the liquid-crystal medium preferably comprises one or more compounds of the formula lll-1g, which are preferably selected from the group of the compounds of the formulae lll-1 g-1 to lll-1g-5, preferably of formula lll-1 g-3:
  • the liquid-crystal medium preferably comprises one or more compounds of the formula lll-1 h, which are preferably selected from the group of the compounds of the formulae lll-1 h-1 to lll-1 h-3, preferably of the formula lll-1 h-3:
  • X 3 preferably denotes F.
  • the liquid-crystal medium preferably comprises one or more compounds of the formula lll-1 i, which are preferably selected from the group of the compounds of the formulae lll-1 i-1 and lll-1 i-2, preferably of the formula 111-1 i-1 :
  • X 3 preferably denotes F.
  • the liquid-crystal medium preferably comprises one or more compounds of the formula lll-1j, which are preferably selected from the group of the compounds of the formulae lll-1j-1 and lll-1j-2, preferably of the formula lll-1j-1 :
  • the liquid-crystal medium preferably comprises one or more compounds of the formula 111-1 k, which are preferably selected from the group of the compounds of the formulae lll-1 k-1 and lll-1 k-2, preferably of the formula lll-1 k-1 :
  • the liquid-crystal medium preferably comprises one or more compounds of the formula III-2.
  • the compounds of the formula III-2 are preferably selected from the group of the compounds of the formulae lll-2a and lll-2b, preferably of formula lll-2b:
  • the liquid-crystal medium preferably comprises one or more compounds of the formula lll-2a, which are preferably selected from the group of the compounds of the formulae lll-2a-1 to lll-2a-6: -2a-1 in which R 3 has the meaning indicated above.
  • the liquid-crystal medium preferably comprises one or more compounds of the formula lll-2b, which are preferably selected from the group of the compounds of the formulae lll-2b-1 to lll-2b-4, preferably lll-2b-4:
  • the media in accordance with the present invention may comprise one or more compounds of the formula III-3
  • These compounds are preferably selected from the group of the formulae lll-3a and lll-3b:
  • liquid crystalline medium comprises additionally to the compounds of formula I and II one or more compounds of formula lll-1 h-3 and one or more compounds of formula lll-1j-1 .
  • the liquid-crystalline media in accordance with the present invention preferably comprise one or more dielectrically neutral compounds having a dielectric anisotropy in the range from -1 .5 to 3.
  • the elements all include their respective isotopes.
  • one or more H in the compounds may be replaced by D, and this is also particularly preferred in some embodiments.
  • a corre- spondingly high degree of deuteration of the corresponding compounds enables, for example, detection and recognition of the compounds. This is very helpful in some cases, in particular in the case of the compounds of formula I.
  • the present application
  • the medium comprises one or more compounds of formula IV-A in which
  • R 41 denotes an unsubstituted alkyl radical having 1 to 7 C
  • R 42 denotes an unsubstituted alkyl radical having 1 to 7 C
  • the group preferably has 2 to 5 C atoms, and preferably is an unsubstituted alkenyl radical having 2, 3 or 4 C atoms, more preferably a vinyl radical or 1 -propenyl radical and in particular a vinyl radical.
  • the medium comprises one or more compounds of formula IV selected from the group of the compounds of the formulae IV-1 to IV-4, preferably of formula IV-1 ,
  • alkyl and alkyl' independently of one another, denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, alkenyl and alkenyl', independently of one another, denote alkenyl having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably 2 C atoms, alkenyl' preferably denotes alkenyl 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 media according to the invention comprise one or more compounds of formula IV-1 and/or one or more compounds of formula IV-2.
  • the medium comprises one or more compounds of formula V.
  • the media according to the invention preferably comprise the following compounds in the total concentrations indicated:
  • the media in accordance with the present invention in addition preferably comprise one or more dielectrically neutral compounds selected from the group of compounds of formulae IV and V, preferably in a total concentration in the range from 5 % or more to 90 % or less, more preferably from 10 % or more to 80 % or less, particularly preferably from 20 % or more to 70 % or less.
  • the medium according to the invention in a particularly preferred embodiment comprises: one or more compounds of formula II in a total concentration in the range from 15 % by weight or more to 65 % or less, preferably in the range from 30 % or more to 55 % or less, and/or one or more compounds of formula III in a total concentration in the range from 5 % or more to 30 % or less.
  • the concentration of the compounds of formula II in the media is in the range from 15 % by weight or more to 65 % or less, more preferably from 15 % or more to 60 % or less, more preferably from 20 % or more to 55 % or less and, most preferably, from 25 % or more to 40 % or less.
  • the present invention also relates to electro-optical displays or electro- optical components which contain liquid-crystalline media according to the invention. Preference is given to electro-optical displays which are based on the IPS or FFS effect, preferably on the IPS effect, and in particular those which are addressed by means of an active-matrix addressing device. Accordingly, the present invention likewise relates to the use of a liquid- crystalline medium according to the invention in an electro-optical display or in an electro-optical component, and to a process for the preparation of the liquid-crystalline media according to the invention, characterised in that one or more compounds of formula I are mixed with one or more compounds of formula II and optionally further compounds and additives.
  • the medium comprises one or more compounds of formula IV, selected from the group of the compounds of the formulae IV-2 and IV-3,
  • alkyl and alkyl' independently of one another, denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, alkoxy denotes alkoxy having 1 to 5 C atoms, preferably having 2 to 4 C atoms.
  • the medium comprises one or more compounds of formula V selected from the group of the compounds of the formulae V-1 and V-2, preferably of formulae V-1 , V-1 in which the parameters have the meanings given above under formula V, and preferably
  • R 51 denotes alkyl having 1 to 7 C atoms or alkenyl having 2 to
  • R 52 denotes alkyl having 1 to 7 C atoms, alkenyl having 2 to 7
  • the medium comprises one or more compounds of formula V-1 selected from the group of the compounds of the formulae V-1 a and V-1 b,
  • alkyl and alkyl' independently of one another, denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, and alkenyl denotes alkenyl having 2 to 7 C atoms, preferably having
  • the media according to the invention may optionally also comprise a di- electrically negative component, whose total concentration is preferably 20 % or less, more preferably 10 % or less, based on the entire medium.
  • the liquid-crystal media according to the invention comprise in total, based on the mixture as a whole,
  • liquid-crystal media in accordance with the present invention may comprise one or more chiral compounds.
  • the liquid-crystalline medium has a birefringence of 0.060 or more, particularly preferably 0.070 or more.
  • the liquid-crystalline medium has a birefringence of 0.200 or less, particularly preferably 0.180 or less.
  • the liquid-crystalline medium has a birefringence in the range from 0.090 or more to 0.160 or less. iv.
  • the liquid-crystalline medium comprises one or more particularly preferred compounds of formula I, preferably selected from the (sub-) formulae 1-1 and I-23, most preferably of (sub-)formula I-23.
  • the total concentration of the compounds of formula II in the mixture as a whole is 25 % or more, preferably 30 % or more, and is preferably in the range from 25 % or more to 49 % or less, particularly preferably in the range from 29 % or more to 47 % or less, and very particularly preferably in the range from 37 % or more to 44 % or less.
  • the liquid-crystalline medium comprises one or more compounds of formula IV selected from the group of the compounds of the following formulae: CC-n-V and/or CC-n-Vm and/or CC-V-V and/or CC-V-Vn and/or CC-nV-Vn, particularly preferably CC-3-V, preferably in a concentration of up to 60 % or less, particularly preferably up to 50 % or less, and optionally additionally CC-3-V1 , preferably in a
  • the media comprise the compound of formula CC-n-V, preferably CC-3-V, preferably in a concentration of 1 % or more to 60 % or less, more preferably in a concentration of 3 % or more to 38 % or less.
  • the total concentration of the compounds of formula CC-3-V in the mixture as a whole preferably either is 15 % or less, preferably 10 % or less or 20 % or more, preferably 25 % or more.
  • the invention furthermore relates to an electro-optical display having active-matrix addressing based on the IPS or FFS effect, characterised in that it contains, as dielectric, a liquid-crystalline medium in accordance with the present invention.
  • the liquid-crystal mixture preferably has a nematic phase range having a width of at least 70 degrees.
  • the rotational viscosity ⁇ - ⁇ is preferably 350 mPa s or less, preferably 250 mPa s or less and, in particular, 150 mPa s or less.
  • the mixtures according to the invention are suitable for all IPS and FFS- TFT applications using dielectrically positive liquid crystalline media, such as, e.g. SG-FFS.
  • the liquid-crystalline media according to the invention preferably virtually completely consist of 4 to 15, in particular 5 to 12, and particularly preferably 10 or less, compounds. These are preferably selected from the group of the compounds of the formulae I, II III, IV, V, VI, VII, VIII and IX.
  • the liquid-crystalline media according to the invention may optionally also comprise more than 18 compounds. In this case, they preferably comprise 18 to 25 compounds. In a preferred embodiment, the liquid-crystal media according to the invention predominantly comprise, preferably essentially consist of and, most preferably, virtually completely consist of compounds, which do not comprise a cyano group. In a preferred embodiment, the liquid-crystal media according to the invention comprise compounds selected from the group of the compounds of the formulae I, II, and II, IV and V, preferably selected from the group of the compounds of the formulae I, 11-1 , II-2, IV and V, they preferably consist predominantly, particularly preferably essentially and very particu- larly preferably virtually completely of the compounds of the said formulae.
  • the liquid-crystal media according to the invention preferably have a nematic phase from in each case at least -10°C or less to 70°C or more, particularly preferably from -20°C or less to 80°C or more, very particularly preferably from -30°C or less to 85°C or more and most preferably from -40°C or less to 90°C or more.
  • 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 no clearing occurs on heating out of 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 cell thickness corresponding to the electro-optical application 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 regarded 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 in capillaries by conventional methods.
  • the liquid-crystal media according to the invention are characterised by optical anisotropy values in the moderate to low range.
  • the birefringence values are preferably in the range from 0.075 or more to 0.130 or less, particularly preferably in the range from 0.085 or more to 0.120 or less and very particularly preferably in the range from 0.090 or more to 0.1 15 or less.
  • the liquid-crystal media according to the invention have a positive dielectric anisotropy and relatively high absolute values of the dielectric anisotropy ⁇ , which preferably is in the range from 9.0 or more to 22 or less, more preferably to 18 or less, more preferably from 10 or more to 15 or less, particularly preferably from 4.0 or more to 9.0 or less and very particularly preferably from 4.5 or more to 8.0 or less.
  • the liquid-crystal media according to the invention preferably have relatively low values for the threshold voltage (Vo) in the range from 1 .0 V or more to 5.0 V or less, preferably to 2.5 V or less, preferably from 1 .2 V or more to 2.2 V or less, particularly preferably from 1 .3 V or more to 2.0 V or less.
  • the liquid-crystal media according to the invention have high values for the VHR in liquid-crystal cells.
  • the values of the VHR of these media are greater than or equal to 95 %, preferably greater than or equal to 97%, particularly preferably greater than or equal to 98 % and very particularly preferably greater than or equal to 99 %, and after 5 minutes in the oven at 100°C in the cells, these are greater than or equal to 90 %, preferably greater than or equal to 93 %, particularly preferably greater than or equal to 96 % and very particularly preferably greater than or equal to 98 %.
  • liquid-crystal media having a low addressing voltage or threshold voltage here have a lower VHR than those having a higher addressing voltage or threshold voltage, and vice versa.
  • These preferred values for the individual physical properties are preferably also in each case maintained by the media according to the invention in combination with one another.
  • the liquid-crystalline media according to the invention comprise one or more compounds of formula I, preferably selected from the group of the formulae 1-1 and/or I-23, and/or one or more compounds of formula II, preferably selected from the group of formulae PUQU-n-F, CDUQU-n-F, APUQU-n-F and PGUQU-n-F, and/or CPUQU-n-F, and/or one or more compounds of formula III, preferably selected from the group of formulae CCP-n-OT, CGG-n-F, and CGG-n-OD, and/or one or more compounds of formulae IV and/or V, preferably selected from the group of formulae CC-n-V, CCP-n-m, CCP-V-n, CCP-V2-n and CGP- n-n, and/or optionally, preferably obligatorily, one or more compounds of formula IV, preferably selected from the group of the compounds of the formulae CC- n-V, CC-n-V
  • composition is preferably 5% or more, particularly preferably 10% or more, very particularly preferably 20% or more, - "predominantly consist of: the concentration of the constituents in
  • composition preferably 50% or more, particularly preferably 55% or more and very particularly preferably 60% or more,
  • composition preferably 80% or more, particularly preferably 90% or more and very particularly preferably 95% or more, and
  • the concentration of the constituents in question in the composition is preferably 98% or more, particularly preferably 99% or more and very particularly preferably 100.0%. This applies both to the media as compositions with their constituents, which can be components and compounds, and also to the components with their constituents, the compounds. Only in relation to the concentra- tion of an individual compound relative to the medium as a whole does the term comprise mean: the concentration of the compound in question is preferably 1 % or more, particularly preferably 2% or more, very particularly preferably 4% or more.
  • “ ⁇ " means less than or equal to, preferably less than, and ">" means greater than or equal to, preferably greater than.
  • the expression “dielectncally positive compounds” means compounds having a ⁇ of > 1 .5
  • the expression “dielectncally neutral compounds” means those where -1 .5 ⁇ ⁇ 1 .5
  • the expression “dielectrically negative compounds” means those where
  • the host mixture used for measuring ⁇ of dielectrically positive and dielectrically neutral compounds is ZLI-4792 and that used for dielectrically negative compounds is ZLI-2857, both from Merck KGaA, Germany.
  • the values for the respective compounds to be investigated are obtained from the change in the dielectric constant of the host mixture after addition of the compound to be investigated and extrapolation to 100% of the compound employed.
  • the compound to be investigated is dissolved in the host mixture in an amount of 10%. If the solubility of the substance is too low for this purpose, the concentration is halved in steps until the investigation can be carried out at the desired temperature.
  • liquid-crystal media according to the invention may, if necessary, also comprise further additives, such as, for example, stabilisers and/or pleo- chroitic, e.g. dichroitic, dyes and/or chiral dopants in the usual amounts.
  • further additives such as, for example, stabilisers and/or pleo- chroitic, e.g. dichroitic, dyes and/or chiral dopants in the usual amounts.
  • the amount of these additives employed is preferably in total 0 % or more to 10 % or less, based on the amount of the entire mixture, particularly preferably 0.1 % or more to 6 % or less.
  • the concentration of the individual compounds employed is preferably 0.1 % or more to 3 % or less. The concentration of these and similar additives is generally not taken into account when specifying the concentrations and concentration ranges of the liquid-crystal compounds in the liquid-crystal media.
  • the liquid-crystal media according to the inven- tion may comprise a polymer precursor which comprises one or more reactive compounds, preferably reactive mesogens, and, if necessary, also further additives, such as, for example, polymerisation initiators and/or polymerisation moderators, in the usual amounts.
  • the amount of these additives employed is in total 0 % or more to 10 % or less, based on the amount of the entire mixture, preferably 0.1 % or more to 2 % or less.
  • concentration of these and similar additives is not taken into account when specifying the concentrations and concentration ranges of the liquid- crystal compounds in the liquid-crystal media.
  • compositions consist of a plurality of compounds, preferably 3 or more to 30 or fewer, particularly preferably 6 or more to 20 or fewer and very particularly preferably 10 or more to 16 or fewer compounds, which are mixed in a conventional manner.
  • the desired amount of the components used in lesser amount is dissolved in the components making up the principal constituent of the mixture. This is advantageously carried out at elevated temperature. If the selected temperature is above the clearing point of the principal constituent, completion of the dissolution operation is particularly easy to observe.
  • the mixtures according to the invention exhibit very broad nematic phase ranges having clearing points of 65°C or more, very favourable values for the capacitive threshold, relatively high values for the holding ratio and at the same time very good low-temperature stabilities at -30°C and -40°C. Furthermore, the mixtures according to the invention are distinguished by low rotational viscosities ⁇ .
  • the media according to the invention may also comprise compounds in which, for example, H, N, O, CI, F have been replaced by the corresponding isotopes.
  • the structure of the IPS liquid-crystal displays according to the invention corresponds to the usual geometry, as described, for example, in US 2001022569 A or US 2002030782 A.
  • liquid-crystal phases according to the invention can be modified by means of suitable additives in such a way that they can be employed in any type of, for example, IPS and FFS LCD display that has been disclosed to date.
  • Table E below indicates possible dopants which can be added to the mixtures according to the invention. If the mixtures comprise one or more dopants, the amount is 0.01 % to 4 %, preferably 0.1 % to 1 .0 %.
  • the liquid crystalline medium comprises additionally a stabiliser selected from the class of phenols, more preferably from the derivatives of 2,6-ditert-butyl phenols, which are preferably those phenols listed in Table F below, and most preferably selected from the group of formulae S-1 and S-2:
  • threshold voltage relates to the capa- citive threshold (Vo), also known as the Freedericks threshold, unless explicitly indicated otherwise.
  • 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 each case in at least one test cell having a cell thickness of 20 ⁇ with homeotropic and with homogeneous surface alignment at 1 kHz.
  • the measurement voltage is typically 0.3 V to 1 .0 V, but is always lower than the capacitive threshold of the respective liquid-crystal mixture investigated.
  • the threshold voltages are determined using test cells produced at Merck.
  • the test cells for the determination of ⁇ have a cell thickness of approximately 20 ⁇ .
  • the electrode is a circular ITO electrode having an area of 1 .13 cm 2 and a guard ring.
  • the orientation layers are SE-121 1 from Nissan Chemicals, Japan, for homeotropic orientation ( ⁇
  • the capacitances are
  • a chiral dopant is not added to the liquid- crystal mixtures used, but the latter are also particularly suitable for applications in which doping of this type is necessary.
  • the rotational viscosity is determined using the rotating permanent magnet method and the flow viscosity in a modified Ubbelohde
  • birefringence are determined at a temperature of 20°C at several fixed wavelengths using a modified Abbe refractometer with homeotropically aligning surfaces on the sides of the prisms in contact with the material.
  • the birefringence values are determined at the specific wavelength values of 436 nm (respective selected spectral line of a low pressure mercury lamp), 589 nm (sodium "D" line) and 633 nm (wavelength of a HE-Ne laser (used in combination with an attenuator/diffusor in order to prevent damage to the eyes of the observers.
  • n H 2n+ i , C m H 2m+ i and QH21+1 or C n H 2n , CmH 2m and Qh i are straight-chain alkyl radicals or alkylene radicals, in each case having n, m and I C atoms respectively.
  • n, m and I are independently of each other 1 , 2, 3, 4, 5, 6, or 7.
  • 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 preferably comprise one or more compounds of the compounds mentioned below.
  • 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 chiral dopants which are preferably employed in the mixtures according to the invention.
  • the media according to the invention comprise one or more compounds selected from the group of the compounds from Table E.
  • Table F shows stabilisers which can preferably be employed in the mixtures according to the invention in addition to the compounds of formula I.
  • the parameter n here denotes an integer in the range from 1 to 12.
  • the phenol derivatives shown can be employed as additional stabilisers since they act as antioxidants.
  • n independently of each other is 1 , 2, 3, 4, 5, 6, or 7.
  • polymerizable stabilizers polymerizable piperidine derivatives
  • Exemplary compounds of formula I are synthesized as follows or according to WO 2016/1 161 19 A1 (examples).
  • Compound RH-2 is prepared as follows.
  • a compound selected from structures S-1 -3 or S-2-3 can advantageously be used, which have the following structures:
  • Mixture (A) is prepared by mixing the host mixture H1 with 0.05 % by weight of non-polymerizable stabilizer S-1 -3. The mixture is investigated with regard to voltage holding ratio before and after backlight load test.
  • Mixture Example 1
  • Test cells with (a) rubbed polyimide and (b) with photo-aligned polyimide are filled with the media of the preceding Examples.
  • the voltage-holding ratio (VHR) of the test cells is measured before and after intensive light load (120 min) for (a) and (b) (Table 1 and 2).
  • the irradiated light is equivalent to 500 h of a typical white CCFL backlight for displays.
  • Table 1 VHR Results, with rubbed polyimide (OPTMER® AL16301 , JSR
  • Comparative Example B Mixture (B) is prepared by mixing the host mixture H1 with 0.05 % by weight of non-polymerizable stabilizer S-2-3. The mixture is investigated with regard to voltage holding ratio before and after backlight load test.
  • Test cells with (a) rubbed polyimide and (b) with photo-aligned polyimide are filled with the media of the preceding Examples and VHR is measured as above (Table 3 and 4).
  • Example 1 By using the polymerizable additives like the compound of the formula RH- 1 or RH-2, the VHR drop after backlight load is avoided.
  • the test cells filled with mixtures of Example 1 to 4 show little decrease of VHR after backlight load, while the comparative examples (Examples A and B) without any polymerizable additive show a considerable VHR drop.

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Abstract

La présente invention concerne un milieu cristallin liquide (milieu CL) comprenant un dérivé de pipéridine polymérisable en tant qu'additif pour la stabilisation, son utilisation à des fins électro-optiques, et des écrans à CL contenant ce milieu, en particulier des écrans à cristaux liquides qui utilisent l'effet IPS (commutation dans le plan) ou FFS (commutation de champ de frange) à l'aide de cristaux liquides diélectriquement positifs.
PCT/EP2018/053988 2017-02-21 2018-02-19 Milieu cristallin liquide et écran à cristaux liquides comportant ledit milieu WO2018153803A1 (fr)

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KR1020197027081A KR20190121791A (ko) 2017-02-21 2018-02-19 액정 매질 및 이를 포함하는 액정 디스플레이
CN201880012776.1A CN110325620A (zh) 2017-02-21 2018-02-19 液晶介质和包含其的液晶显示器

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