WO2018206538A1 - Milieu à cristaux liquides - Google Patents

Milieu à cristaux liquides Download PDF

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Publication number
WO2018206538A1
WO2018206538A1 PCT/EP2018/061784 EP2018061784W WO2018206538A1 WO 2018206538 A1 WO2018206538 A1 WO 2018206538A1 EP 2018061784 W EP2018061784 W EP 2018061784W WO 2018206538 A1 WO2018206538 A1 WO 2018206538A1
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atoms
compounds
switching
medium
another
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PCT/EP2018/061784
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English (en)
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Yuko Arai
Hideo Ichinose
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Merck Patent Gmbh
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Priority to JP2019561933A priority Critical patent/JP7293130B2/ja
Publication of WO2018206538A1 publication Critical patent/WO2018206538A1/fr

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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)
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/062—Non-steroidal liquid crystal compounds containing one non-condensed benzene ring
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    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
    • C09K19/3447—Pyridine condensed or bridged with another ring system, e.g. quinoline or acridine
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458—Uncondensed pyrimidines
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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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    • C09K19/06—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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    • C09K19/06—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
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
    • C09K2019/181—Ph-C≡C-Ph
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3009—Cy-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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/301—Cy-Cy-Ph
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    • C09K19/04—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
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    • C09K19/00—Liquid crystal materials
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
    • C09K2019/3063—Cy-Ph-C≡C-Ph
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    • 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
    • C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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    • C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
    • C09K2219/13—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used used in the technical field of thermotropic switches

Definitions

  • the present invention relates to a liquid crystal (LC) medium comprising a polymerisable compound, to a process for its preparation, to its use for optical, electro-optical and electronic purposes, in particular in a switching device for regulating the passage of light through an area element, like a switchable window.
  • LC liquid crystal
  • Window elements having darkenable switching layers which allow various degrees of absorption of daylight are known to the person skilled in the art.
  • window elements are frequently based on switching layers comprising liquid-crystalline (LC) media which are addressed by applied electrodes, as disclosed for example in US 2016/033807 A.
  • a window element which contains a switching element having one of the switching layers described above can be switched between the "bright” and “dark” states, so that shading of a room which contains the window element as light-transmitting component of the window(s) in its outside wall is achieved in the "dark” switching state, where the extent of shading can be regulated by a voltage applied to the switching element.
  • the present invention therefore has the object of providing a window element containing a switching element, which makes it possible to regulate the dazzling by sunlight in a room independently from the brightness necessary in the room thereby avoiding the necessity of artificial lighting.
  • Polymer dispersed liquid crystal (PDLC) films have considerable potentials for flexible display, transparent display and smart window since they can be switched electrically.
  • the normally hazy PDLC mode which is switched from hazy to transparent is popular due to its easy manufacturing.
  • a window having a normally hazy appearance without voltage can be a disadvantage.
  • the inventors have revealed, that for a window
  • a normally transparent mode PDLC could be more preferable.
  • One solution presented here is a normally transparent polymer network LC device. Anisotropic gels based on liquid crystals containing a network of photo- polymerised liquid-crystalline (LC) molecules were used for reversible switching a LC display cell from no scattering to scattering mode by application of an electric field (R.M.A. Hikmet, J. Appl. Phys. 68(9), 1990, 4406-4412).
  • another object of the invention is to provide a switching layer for use in a switching element which enables switching from a transparent state into an opaque, i.e. non-transparent state of the switching element.
  • the opaque state here is a state in which the light passing through the switching element is scattered.
  • the opaque switching state shall cause one or more effects selected from reduction of dazzling, as mentioned above, and the establishment of privacy.
  • a further aim of the current invention is easy manufacturing of a large area optical device like window panes and other transparent building elements.
  • the deposition of thin functional layers on large glass substrates is usually combined with considerable technical effort.
  • the invention relates to a liquid crystal (LC) medium comprising one or more polymerisable compounds, one or more compounds selected from formulae CY and PY, and one or more compounds of formula TO
  • a denotes 1 or 2
  • b denotes 0 or 1
  • L 1"4 each, independently of one another, denote F, CI, OCF3, CF3,
  • a further subject of the current invention is an LC medium comprising
  • a low-molecular-weight LC component (hereinafter also referred to as "host mixture"), comprising one or more compounds selected from formulae CY and PY, and one or more compounds of formula TO, and
  • polymerisable component comprising one or more polymerisable
  • the invention furthermore relates to an LC medium as described above and below, wherein the polymerisable compounds are polymerised.
  • the invention further relates to the use of the LC medium as described above and below in a switching device for regulating the passage of light through an area element, very preferably a switchable window.
  • the invention furthermore relates to a switching device for regulating the passage of light through an area element, very preferably a switchable window, comprising an LC medium according to the invention, wherein preferably the polymerisable compounds of the LC medium are polymerised to form a polymer network.
  • the invention further relates to a switching layer for use in a switching device, wherein the switching layer has a transparent switching state and a scattering switching state and comprises, between an upper switching layer plane USLP and a lower switching layer plane LSLP, an LC medium comprising at least
  • low-molecular-weight LC component and the polymerisable or polymer component are as defined above and below.
  • the invention further relates to a switching layer for use in a switching element, where the switching layer has a transparent switching state and a scattering switching state and comprises an LC medium between an upper switching layer plane and a lower switching layer plane, characterized in that the LC medium is as described above and below.
  • the LC medium of the switching layer comprises nematically arranged molecules.
  • the polymerisable compounds in the LC medium of the switching layer are polymerised to form a polymer network.
  • the invention further relates to a switching device comprising a switching layer as described above and below.
  • the switching layer is arranged in a first layer sequence, and where the first layer sequence comprises, from the outside inward,
  • the invention further relates to a switchable window comprising a switching layer or a switching device as described above and below.
  • the invention furthermore relates to a process for manufacturing a switching device as described above and below, comprising the steps of filling or otherwise providing an LC medium, which comprises one or more polymeri- sable compounds as described above and below, between two plane-parallel substrates which are optionally equipped with one or more additional layers like transparent electrodes or alignment layers, and polymerising the polymerisable compounds.
  • the polymerisable compounds are preferably polymerised by photo- polymerisation, very preferably by UV photopolymerisation.
  • 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 CY and/or PY with one or more compounds of formula TO and with one or more poylmerisable compounds, and optionally with further LC compounds and/or additives.
  • Fig. 1 shows the transmission vs. voltage graph for switching devices containing a polymerisable mixture of Example 3 or 4, respectively.
  • switching layer and “switching device” will be understood to mean a layer or device that is switchable between two states, causing a change in the passage of light through the layer or device, and preferably wherein the two states have different light transmission, for example by applying a voltage.
  • the term "light rays" will be understood to mean electro- magnetic rays in the UV-A, VIS and NIR region. In particular, it will be understood to mean light rays having a wavelength which is not absorbed or only absorbed to a negligible extent by the materials (for example glass) usually used in windows. According to definitions usually used, the UV-A region will be understood to mean a wavelength of 320 nm to 380 nm, the VIS region to mean a wavelength of 380 nm to 780 nm and the NIR region to mean a wavelength of 780 nm to 2000 nm.
  • dichroic dye will be understood to mean a light- absorbent compound whose absorption properties are dependent on the orientation of the molecules relative to the direction of polarisation of the light.
  • a dichroic dye in accordance with the present application has an elongate shape, i.e. the dye molecules are significantly longer in one spatial direction (longitudinal axis) than in the other two spatial directions.
  • liquid-crystalline (LC) medium will be understood to mean a material which has liquid-crystalline properties under certain conditions.
  • An LC medium in accordance with the invention typically comprises at least one compound whose molecules have an elongate form, i.e. are significantly longer in one spatial direction (longitudinal axis) than in the other two spatial directions.
  • the LC medium preferably has a nematic phase.
  • unpolymerisable 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 polymerisabe compounds or RMs.
  • mesogenic group as used herein is known to the person skilled in the art and described in the literature, and means a group which, due to the anisotropy of its attracting and repelling interactions, essentially contributes to causing a liquid-crystal (LC) phase in low-molecular-weight or polymeric substances.
  • Compounds containing mesogenic groups do not necessarily have to have an LC phase themselves. It is also possible for mesogenic compounds to exhibit LC phase behaviour only after mixing with other compounds and/or after polymerisation. Typical mesogenic groups are, for example, rigid rod- or disc-shaped units.
  • reactive mesogen and "RM” will be understood to mean a compound containing a mesogenic or liquid crystalline skeleton, and one or more functional groups attached thereto which are suitable for polymerisation and are also referred to as “polymerisable group” or "P".
  • polymerisable compound as used herein will be understood to mean a polymerisable monomeric compound.
  • the polymerisable compounds are preferably selected from achiral compounds.
  • 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, 1 16, 6340-6368.
  • spacer group or “spacer” mean a flexible group, for example an alkylene group, which connects the mesogenic group and the polymerisable group(s) in a polymerisable mesogenic compound.
  • halogen denotes F, CI, Br or I, preferably F or CI.
  • alkyl also encompass polyvalent groups, for example alkylene, arylene, heteroarylene, etc.
  • aryl denotes an aromatic carbon group or a group derived therefrom
  • heteroaryl denotes "aryl” as defined above, containing one or more heteroatoms, preferably selected from N, O, S, Se, Te, Si and Ge.
  • Preferred alkyl groups are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cydopentyl, n-hexyl, cyclohexyl, 2-ethylhexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, dodecanyl, trifluoromethyl, perfluoro- n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, perfluorohexyl, etc.
  • Preferred alkenyl groups are, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, etc.
  • Preferred alkynyl groups are, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl, etc.
  • Preferred alkoxy groups are, for example, methoxy, ethoxy, 2-methoxy- ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2- methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n- decoxy, n-undecoxy, n-dodecoxy, etc.
  • Preferred amino groups are, for example, dimethylamino, methylamino, methylphenylamino, phenylamino, etc. is preferably
  • the LC low-molecular-weight component used for the switching layer can vary in a broad range, wherein media having the preferred characteristics as disclosed herein are preferred.
  • the LC medium according to the present invention preferably has a negative dielectrical anisotropy ⁇ , which works well with electrodes on opposite substrate sides. A variety of suitable and preferred compounds is shown in the preferred embodiments below.
  • Compounds selected from the formulae CY, PY, T and TO are especially preferred. Especially compounds of formulae CY, PY, T, YC, Y, Fl, N, BC, CR, RC, PH and BF will contribute to a negative ⁇ .
  • one or more compounds selected from formulae ZK, DK, VK and B, which are preferably dielectrically neutral, may be added to the LC medium for fine-tuning the physical and electrroptical properties.
  • the processed LC medium of switching layer is forwards-scattering in at least one state of the switching layer, preferably in the voltage driven state.
  • the switching layer works similar to a polymer-dispersed LC device (PDLC device) on the principle of scattering in the "dark" state, and non-scattering in the bright state.
  • Td is indicated here averaged over the spectral region from
  • the diffusive haze H (also referred to as haze) is defined herein in
  • Td is defined in accordance with formula (1 ) as above.
  • the switching layer according to the invention built into a switching element, allows, optionally in addition to regulation by means of bright/dark states, the ability to regulate the dazzling by sunlight without the need to effect the requisite room brightness by means of artificial room lighting.
  • This is regarded as very pleasant by many people and in addition reduces the energy demand of a building having window elements which contain switching elements having the switching layer according to the invention.
  • energy-saving, transparent or flexible display devices can also be accomplished with the switching layers according to the invention.
  • the production of the elements is advantageously associated with little effort, since, inter alia, "alignment layers" do not have to be applied to the substrates.
  • the LC medium is usually introduced between parallel substrates of e.g. glass or plastics (polymer).
  • the alignment additive will effect vertical alignment of the longitudinal axis of the LC molecules with respect to the substrate plane.
  • the dielectric anisotropy of the LC is negative, typically with a dielectric anisotropy of ⁇ ⁇ 1 .5.
  • This design allows a switching operation from transparent to scattering by an electric field between the substrates.
  • a suitable switching voltage is supplied to which a suitable switching voltage is supplied.
  • a rectangular AC voltage is used for switching.
  • switching states is principally taken to mean binary states in which the switching layer according to the invention may exist, i.e.
  • the switching layer according to the invention may have further switching states, in particular intermediate states.
  • the switching layer according to the invention if it is combined with further switching layers in a switching element, allows switching between a completely private state and a state with visual contact with the outside.
  • the visual contact with the outside is a property which is not offered by awnings and blinds.
  • both L 1 and L 2 denote F or one of L 1 and L 2 denotes F and the other denotes CI
  • both L 3 and L 4 denote F or one of L 3 and L 4 denotes F and the other denotes CI.
  • the compounds of the formula CY are preferably selected from the group consisting of the following sub-formulae:
  • 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.
  • the compounds of the formula PY are preferably selected from the group consisting of the following sub-formulae:
  • 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.
  • a preferred LC medium contains one or more compounds of formula CY2 and one or more compounds of formula PY10.
  • the total concentration of the compounds of formula CY and PY and their subformulae in the low-molecular-weight LC component of the LC medium is from 10 to 50% by weight, very preferably from 10 to 30% by weight.
  • the concentration of the compounds of formula CY and its subformulae in the low-molecular-weight LC component of the LC medium is from 5 to 30% by weight, very preferably from 5 to 20% by weight.
  • the concentration of the compounds of formula PY and its subformulae in the low-molecular-weight LC component of the LC medium is from 5 to 20% by weight, very preferably from 5 to 15% by weight.
  • Preferred compounds of formula TO are those wherein L 3 is H.
  • the compounds of formula TO are preferably selected from the following formulae
  • R 1 and R 2 are as defined above.
  • R 1 and R 2 are particularly preferably alkyl or alkoxy having 1 to 8 carbon atoms.
  • Very preferably R 1 is alkyl with 1 to 6 C atoms and R 2 is alkoxy with 1 to 6 C atoms.
  • LC media comprising one or more compounds selected from formulae TO1 and TO2, and one or more compounds selected from formula TO3 and TO4.
  • LC media comprising one or more compounds of formula TO1 , one or more compounds of formula TO2, one or more compounds of formula TO3 and one or more compounds of formula TO4.
  • the concentration of the compounds of formula TO in the low- molecular-weight LC component of the LC medium is from 20 to 80%, very preferably from 30 to 75%, most preferably from 35 to 65%.
  • R 1 and R 2 have the meanings given in formula CY
  • L T1 ⁇ T6 denote, each independently of one another, H, F or CI, with at least one of L T1 to L T6 being F or CI.
  • the compounds of the formula T are preferably selected from the group consisting of the following sub-formulae:
  • R denotes a straight-chain alkyl or alkoxy radical having 1-7 C atoms
  • R* denotes a straight-chain alkenyl radical having 2-7 C atoms
  • (O) denotes an oxygen atom or a single bond
  • m denotes an integer from 1 to 6.
  • R and R * preferably denote methyl, ethyl, propyl, butyl, pentyl, hexyl, meth- oxy, ethoxy, propoxy, butoxy or pentoxy.
  • the concentration of compounds of formula T or T1 -T24 in the low- molecular-weight LC component of the LC medium is from 5 to 20%, very preferably from 5 to 15%.
  • the LC medium contains 1 to 5, very preferably 1 or 2 compounds of formula T or T1 -T24.
  • LC media are selected from the following embodiments or any combinartiohn thereof: a) LC medium which additionally comprises one or more compounds of the following formula:
  • R 3 and R 4 each, independently of one another, denote alkyl having 1 to
  • the compounds of the formula ZK are preferably selected from the group consisting of the following sub-formulae:
  • 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.
  • Particularly preferred compounds of formula ZK are selected from the following sub-formulae:
  • propyl, butyl and pentyl groups are straight-chain groups.
  • e denotes 1 or 2.
  • the compounds of the formula DK are preferably selected from the group consisting of the following sub-formulae:
  • 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.
  • LC medium which additionally comprises one or more compounds selected from the group consisting of the following formulae:
  • LC medium which additionally comprises one or more compounds selected from the group consisting of the following formulae:
  • R 5 has one of the meanings indicated above for R 1 , alkyl denotes Ci-6-alkyl, d denotes 0 or 1 , and z and m each, independently of one another, denote an integer from 1 to 6.
  • R 5 in these compounds is particularly preferably Ci-6-alkyl or -alkoxy or C2-6-alkenyl, d is preferably 1 .
  • the low-molecular-weight LC component of the LC medium i.e.
  • LC medium which additionally comprises one or more biphenyl compounds selected from the group consisting of the following formulae:
  • 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.
  • the proportion of the biphenyls of the formulae B1 to B3 in the low- molecular-weight LC component of the LC medium is preferably at least 3% by weight, in particular > 5% by weight.
  • the compounds of the formula B2 are particularly preferred.
  • the compounds of the formulae B1 to B3 are preferably selected from the group consisting of the following sub-formulae:
  • LC medium particularly preferably comprises one or more compounds of the formulae B1 a and/or B2c.
  • LC medium which additionally comprises one or more compounds of the following formula: in which
  • R 9 denotes H, CH 3 , C2H5 or n-C3H 7
  • (F) denotes an optional fluorine substituent
  • q denotes 1 , 2 or 3
  • R 7 has one of the meanings indicated for R 1 , preferably in amounts of > 3% by weight, in particular > 5% by weight and very particularly preferably 5-30% by weight, based on the low-molecular-weight LC component of the LC medium (i.e. excluding the polymerisable component).
  • Particularly preferred compounds of the formula Fl are selected from the group consisting of the following sub-formulae:
  • R 7 preferably denotes straight-chain alkyl
  • R 9 denotes
  • LC medium which additionally comprises one or more compounds selected from the group consisting of the following formulae:
  • R 8 has the meaning indicated for R 1
  • alkyl denotes a straight-chain alkyl radical having 1 -6 C atoms.
  • LC medium which additionally comprises one or more compounds which contain a tetrahydronaphthyl or naphthyl unit, such as, for example, the compounds selected from the group consisting of the following formulae:
  • LC medium which additionally comprises one or more difluorodibenzo- chromans and/or chromans of the following formulae:
  • R 11 and R 12 each, independently of one another, have one of the
  • ring M is trans-1 ,4-cyclohexylene or 1 ,4-phenylene
  • c 0, 1 or 2
  • Particularly preferred compounds of the formulae BC, CR and RC are selected from the group consisting of the following sub-formulae:
  • alkyl and alkyl * each, independently of one another, denote a straight-chain alkyl radical having 1 -6 C atoms
  • (O) denotes an oxygen atom or a single bond
  • c is 1 or 2
  • mixtures comprising one, two or three compounds of the formula BC-2.
  • LC medium which additionally comprises one or more fluorinated phenanthrenes and/or dibenzofurans of the following formulae:
  • R 11 and R 12 each, independently of one another, have one of the meanings indicated above for R 11 , b denotes 0 or 1 , L denotes F, and r denotes 1 , 2 or 3.
  • Particularly preferred compounds of the formulae PH and BF are selected from the group consisting of the following sub-formulae:
  • LC medium which additionally comprises one or more monocyclic compounds of the following formula
  • R 1 and R 2 each, independently of one another, denote alkyl having 1 to
  • L 1 and L 2 each, independently of one another, denote F, CI, OCF3,
  • both L 1 and L 2 denote F or one of L 1 and L 2 denotes F and the other denotes CI,
  • the compounds of the formula Y are preferably selected from the group consisting of the following sub-formulae:
  • 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 Y are selected from the group consisting of the following sub-formulae:
  • Alkoxy preferably denotes straight-chain alkoxy with 3, 4, or 5 C atoms.
  • said switching layer contains an LC medium which is preferably selected from one of the preferred embodiments as described above and below, and which comprises nematically arranged LC molecules, and said switching layer further contains a polymer network which is formed by polymerisation of polymerisable compounds and which is preferably dispersed in the LC medium of the switching layer.
  • the nematically arranged molecules are preferably employed in the form of a mixture of nematic LC molecules (or LC host mixture) with a polymer network being dispersed therein.
  • the polymer network is formed from a polymerisable component contained in the LC host mixture, which contains one or more polymerisable compounds and optionally one or more photoinitiators.
  • the LC medium according to the present invention further comprises a polymerisable component containing one or more polymerisable compounds, which are preferably selected from polymerisable mesogenic compounds, also known as reactive mesogens, and optionally one or more photoinitators.
  • the LC medium comprises one or more polymerisable compounds selected from formula I
  • R a -B 1 -(Z b -B 2 ) m -R b I in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
  • R a and R b P, P-Sp-, H, F, CI, Br, I, -CN, -NO 2 , -NCO, -NCS, -OCN, -SCN,
  • O-, -O-CO-, -O-CO-O- in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, CI, Br, I, CN, P or
  • R a and/or R b may also denote a radical which is spiro-linked to this saturated C atom, wherein at least one of the radicals R a and R b denotes or contains a group P or P-Sp-
  • Particularly preferred compounds of the formula I are those in which B 1 and B 2 each, independently of one another, denote 1 ,4-phenylene, 1 ,3- phenylene, naphthalene-1 ,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7- diyl, 9,10-dihydro-phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7- diyl, coumarine, flavone, where, in addition, one or more CH groups in these groups may be replaced by N, cyclohexane-1 ,4-diyl, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by O and/or S, 1 ,4- cyclohexenylene, bicycle[1 .1 .1 ]pentane-1 ,3-diyl, bicyclo[2.2.2]o
  • Particularly preferred compounds of the formula I are those in which B 1 and B 2 each, independently of one another, denote 1 ,4-phenylene, 1 ,3- phenylene, naphthalene-1 ,4-diyl or naphthalene-2,6-diyl.
  • the polymerisable group P is a group which is suitable for a polymerisation reaction, such as, for example, free-radical or ionic chain polymerisation, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain.
  • a polymerisation reaction such as, for example, free-radical or ionic chain polymerisation, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain.
  • groups which are suitable for polymerisation with ring opening such as, for example, oxetane or epoxide groups.
  • radicals L as defined above which are other than P-Sp-, ki, k 2 and k3 each, independently of one another, denote 0 or 1 , k3 preferably denotes 1 , and k 4 denotes an integer from 1 to 10.
  • CH 2 CW 2 -O-
  • CH 2 CW 2 -
  • CW 1 CH-CO-(O)k3-
  • polymerisable groups P are selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide, most preferably from acrylate and methacrylate.
  • Sp is different from a single bond, it is preferably of the formula Sp"-X", so that the respective radical P-Sp- conforms to the formula P-Sp"-X"-, wherein
  • X denotes -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CO-N(R 0 )-, -N(R 0 )- CO-, -N(R°)-CO-N(R 00 )-, -OCH 2 -, -CH 2 O-, -SCH 2 -, -CH 2 S-, -CF 2 O-, - OCF 2 -, -CF 2 S-, -SCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 -, -CH 2 -, -CH 2 -, -CH 2 -, -CH 2 CF 2 -, -CH 2 -, -CH 2 -, -CH 2 CF 2 -, -CH 2 -, -CH 2 -, -CH 2 -, -
  • R° and R 00 each, independently of one another, denote H or alkyl having 1 to 20 C atoms, and
  • Y 2 and Y 3 each, independently of one another, denote H, F, CI or CN.
  • X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR°- CO-, -NR°-CO-NR 00 - or a single bond.
  • Typical spacer groups Sp and -Sp"-X"- are, for example, -(CH 2 ) p1 -, -(CH 2 CH2O)qi-CH 2 CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2- or -(SiR°R 00 -O)pi-, in which p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R° and R 00 have the meanings indicated above.
  • Sp and -Sp"-X"- are -(CH2) P i-, -(CH2) P i-O-, -(CH 2 ) P i-O-CO-, -(CH 2 ) P i-CO-O-, -(CH 2 ) P i-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-methylimino- ethylene, 1 -methylalkylene, ethenylene, propenylene and butenylene.
  • Very preferred compounds of formula I are selected from the following formulae:
  • P 1 , P 2 , P 3 one of the meanings given for P, preferably a vinyloxy
  • Sp 1 , Sp 2 , Sp 3 one of the meanings given for Sp, wherein one or more of the radicals P 1 -Sp 1 -, P 1 -Sp 2 - and P 3 - Sp 3 - may also denote R aa , with the proviso that at least one of the radicals P 1 -Sp 1 -, P 2 -Sp 2 and P 3 -Sp 3 - present is different from R aa ,
  • R aa H, F, CI, CN or straight-chain or branched alkyl having 1 to
  • branched radicals have at least three C atoms
  • L is preferably F, CI, CN, NO 2 , CH 3 , C 2 H 5 , C(CH 3 ) 3 , CH(CH 3 ) 2 ,
  • Preferred compounds of formulae M1 to M33 are those wherein P 1 , P 2 and P 3 denote an acrylate, methacrylate, oxetane or epoxy group, very preferably an acrylate or methacrylate group.
  • Preferred compounds of formulae M1 to M31 are those wherein Sp 1 , Sp 2 and Sp 3 are a single bond.
  • Further preferred compounds of formulae M1 to M31 are those wherein one of Sp 1 , Sp 2 and Sp 3 is a single bond and another one of Sp 1 , Sp 2 and Sp 3 is different from a single bond.
  • Further preferred compounds of formulae M1 to M33 are those wherein those groups Sp 1 , Sp 2 and Sp 3 that are different from a single bond denote - (CH 2 )si-X"-, wherein s1 is an integer from 1 to 6, preferably 2, 3, 4 or 5, and X" is X" is the linkage to the benzene ring and is -O-, -O-CO-, -CO-O, -O-CO- O- or a single bond.
  • compounds of formulae M2 and M13 especially direactive compounds containing exactly two polymerisable groups P 1 and P 2 .
  • compounds of formulae M2 and M13 wherein one of the groups Sp 1 and Sp 2 is a single bond and the other of the groups Sp 1 and Sp 2 is different from a single bond.
  • compounds of formulae M2 and M13 containing at least one substituent L selected from F, CI, methyl, ethyl, methoxy, ethoxy, fluorinated methyl or methoxy and fluorinated ethyl or ethoxy, very preferably F.
  • compounds M15 to M31 in particular M17, M18, M19, M22, M23, M24, M25, M26, M30 and M31 , especially trireactive compounds containing exactly three polymerisable groups P 1 , P 2 and/or P 3 .
  • polymerisable compounds in the LC medium or the polymerisable component are selected, preferably exclusively, from the following formulae
  • P 1 , P 2 , Sp 1 , Sp 2 , L and r have the meanings given above, and at least one one of Sp 1 and Sp 2 is a single bond.
  • P 1 and P 2 denote methacrylate.
  • at least one of r is 1 or 2
  • L is preferably F, CI, CH 3 , OCH3, C2H5, OC2H5 or OCF3 , very preferably F.
  • polymerisable compounds in the LC medium or the polymerisable component are selected, preferably exclusively, from the following formula
  • P 1 , P 2 , Sp 2 , L and r have the meanings given above an below, and Sp 2 is different from a single bond.
  • P 1 and P 2 denote methacrylate.
  • at least one of r is 1 or 2
  • L is preferably F, CI, CH 3 , OCH 3 , C2H5, OC2H5 or OCF 3 , very preferably F.
  • Preferred compounds of formula M13a are those selected from formulae RM- 53, RM-55, RM-57, RM-59, RM-61 , RM-63, RM-65, RM-67, RM-69 and RM- 71 , very preferably formula RM-55, RM-57, RM-59, RM-67, most preferably formula RM-59.
  • the LC medium contains a polymerisable component comprising one or more polymerisable compounds selected from formula M1 1 , M32 and M33, wherein in formula M1 1 preferably one or both of Z 2 and Z 3 denote COO or OCO.
  • LC media comprising one, two or three polymerisable compounds, preferably selected of formula I or its subformulae as shown above and below.
  • the polymensable component in the LC medium comprises one or more polymensable compounds comprising two or more polymerisable groups (di- or multireactive or di- or multifunctional compounds).
  • the polymerisable component comprises a plurality of polymerisable compounds.
  • the polymerisable component comprises a plurality of polymerisable compounds, at least one of which is a polymerisable compound containing only one polymerisable group
  • polymerisable compounds comprising two or more polymerisable groups (di- or multireactive or di- or multifunctional compounds).
  • the polymerisable component is in the range ⁇ 50%, more preferably ⁇ 30% and very preferably ⁇ 25% by weight, and preferably ⁇ 3%, more preferably ⁇ 5%, very preferably ⁇ 10% by weight.
  • the proportion of the low-molecular-weight LC component, based on the LC medium as a whole is in the range ⁇ 50%, more preferably ⁇ 70 %, very preferably ⁇ 75 % by weight, and preferably ⁇ 97%, more preferably ⁇ 95%, very preferably ⁇ 90% by weight.
  • the polymerisable compounds Upon polymerisation the polymerisable compounds form a crosslinked polymer, or polymer network, which is preferably dispersed throughout the LC medium contained in the switching layer.
  • the nematically arranged molecules and the polymeric network are preferably homogeneously distributed in one another. This means that, at least visually or on a macroscopic scale, no droplet formation of the nematically arranged molecules is observed. Without being bound by theory, it is believed that the polymer network forms domains on a microscopic scale, which could be attributed to the generation of haze.
  • the polymerisation of the polymerisable compounds in the LC medium can be carried out in one step or in two or more steps, wherein the polymerisation conditions like UV exposure time, temperature, radiation energy etc. can be varied in the individual polymerisation steps.
  • Suitable and preferred polymerisation methods are, for example, thermal or photopolymerisation, preferably photopolymerisation, in particular UV induced photopolymerisation, which can be achieved by exposure of the polymerisable compounds to UV radiation.
  • LC medium additionally comprises one or more polymerisation initiators to initiate or enhance polymerisation.
  • polymerisation initiators to initiate or enhance polymerisation.
  • suitable conditions for the polymerisation and suitable types and amounts of initiators are known to the person skilled in the art and are described in the literature.
  • Suitable for free- radical polymerisation are, for example, the commercially available
  • Preferred photoinitiators are selected from benzophenone derivatives, very preferably from the following structural formulae:
  • the LC medium contains one or more photoinitiators selected from phosphine oxide derivatives, very preferably from the following formulae
  • TPO 2,4,6-Trimethylbenzoyl-diphenyl-phosphine oxide
  • the concentration of polymerisation initiators in the LC medium as a whole is preferably from 0.01 to 2%, very preferably from 0.1 to 1 %.
  • the polymerisation initiators are part of the polymerisable component of the LC medium.
  • the polymerisable compounds according to the invention are also suitable for polymerisation without an initiator, which is accompanied by considerable advantages, such, for example, lower material costs and in particular less contamination of the LC medium by possible residual amounts of the initiator or degradation products thereof.
  • the polymerisation can thus also be carried out without the addition of an initiator.
  • the LC medium thus does not contain a polymerisation initiator.
  • the LC medium may also comprise one or more stabilisers in order to prevent undesired spontaneous polymerisation of the RMs, for example during storage or transport. Suitable types and amounts of stabilisers are known to the person skilled in the art and are described in the literature.
  • stabilisers from the Irganox® series (Ciba AG), such as, for example, Irganox® 1076. If stabilisers are employed, their proportion, based on the total amount of RMs or the polymerisable component (component A), is preferably 10-500,000 ppm, particularly preferably 50-50,000 ppm.
  • the LC medium in addition to the low-molecular-weight component and the polymerisable or polymerised component, contains a dye component comprising one or more dyes, preferably selected from dichroic dyes.
  • the dyes are preferably organic compounds, particularly preferably organic compounds containing at least one condensed aryl or heteroaryl group.
  • the LC medium preferably comprises at least two, particularly preferably at least three and very particularly preferably three or four different dyes.
  • two or more dyes are present in the mixture, they are preferably selected such that their absorption spectra complement one another in such a way that essentially the entire visible spectrum of light is absorbed.
  • the impression of a black colour thus arises for the human eye.
  • This is preferably achieved by using three or more different dyes, at least one of which absorbs blue light, at least one of which absorbs green to yellow light and at least one of which absorbs red light.
  • Light colour here is defined in accordance with B. Bahadur, Liquid Crystals - Applications and Uses, Vol. 3, 1992, World Scientific Publishing, section 1 1 .2.1 .
  • the total proportion of the dyes in the LC medium as a whole is preferably from 0.01 to 20%, more preferably from 0.1 to 15% and very preferably from 0.2 to 12% by weight.
  • the proportion of each individual dye in the LC medium as a whole is preferably from 0.01 to 15%, more preferably from 0.05 to 12% and very preferably from 0.1 to 10% by weight.
  • the dyes present in the LC medium are preferably dissolved in the LC medium.
  • the dyes are preferably influenced in their alignment by the alignment of the molecules of the LC medium mixture in the LC state.
  • the dyes are preferably selected from dichroic dyes, particularly preferably positively dichroic dyes.
  • Positively dichroic is taken to mean that the dye has a positive degree of anisotropy R.
  • the degree of anisotropy R is particularly preferably greater than 0.4, very particularly preferably greater than 0.5 and most preferably greater than 0.6.
  • the degree of anisotropy R is determined as indicated in the working examples of the application text WO2015/154848.
  • the dyes may also be preferred for the dyes to be negatively dichroic. Negatively dichroic is taken to mean that the dye has a negative degree of anisotropy R.
  • the dyes present in the LC medium are preferably either all positively dichroic, or all negatively dichroic.
  • the dyes in accordance with the present application absorb predominantly light in the UV-VIS-NIR region, i.e. in a wavelength range from 320 to 1500 nm.
  • the dyes particularly preferably absorb predominantly light in the VIS region, i.e. in a wavelength range from 380 to 780 nm.
  • the dyes particularly preferably have one or more absorption maxima in the UV-VIS-NIR region defined above, preferably in the VIS region, i.e. a wavelength of 380 nm to 780 nm.
  • the dye is furthermore preferably selected from the dye classes indicated in B. Bahadur, Liquid Crystals - Applications and Uses, Vol. 3, 1992, World Scientific Publishing, section 1 1 .2.1 , and particularly preferably from the explicit compounds shown in the table.
  • the dyes are preferably selected from azo compounds, anthraquinones, methine compounds, azomethine compounds, merocyanine compounds, naphthoquinones, tetrazines, rylenes, in particular perylenes and terylenes, benzothiadiazoles, pyrromethenes and diketopyrrolopyrroles.
  • the switching layer comprises no dyes.
  • This has the advantage of a simpler structure of the switching element or higher transmission in the bright state, or both.
  • the optical appearance of the switching element in this case is white, i.e.
  • the LC medium may additionally comprise one or more further components or additives, preferably selected from the list including but not limited to co- monomers, chiral dopants, polymerisation initiators, inhibitors, stabilizers, surfactants, wetting agents, lubricating agents, dispersing agents,
  • hydrophobing agents adhesive agents, flow improvers, defoaming agents, deaerators, diluents, reactive diluents, auxiliaries, colourants, pigments and nanoparticles.
  • the LC media according to the present invention may, for example, also comprise one or more UV stabilisers, such as Tinuvin ® from Ciba Chemicals, in particular Tinuvin ® 770, antioxidants, free-radical scavengers,
  • UV stabilisers such as Tinuvin ® from Ciba Chemicals, in particular Tinuvin ® 770, antioxidants, free-radical scavengers,
  • the LC media according to the present invention may, for example, also comprise one or more chiral dopants, preferably in a concentration from 0.01 to 1 %, very preferably from 0.05 to 0.5%.
  • Suitable chiral dopants are mentioned below in Table B.
  • Preferred chiral dopants are for example selected from R- or S-101 1 , R- or S-201 1 , R- or S-301 1 , R- or S-401 1 , or R- or S- 501 1 .
  • 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. Cryst.
  • the LC 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 like deuterium etc.
  • the LC medium of the switching layer according to the invention preferably has a specific resistance of > 1 .0-10 9 ohm-cm, particularly preferably > 1 .0- 10 11 ohm-cm.
  • the LC medium according to the invention preferably retains a nematic phase down to -20°C and preferably down to -30°C, particularly preferably down to -40°C, and preferably has a clearing point > 90°C, preferably > 95°C, more preferably > 100°C or > 105°C and very particularly preferably > 1 10°C
  • the LC medium of the present invention preferably has a nematic phase range of at least 100 K, more preferably at least 120K and most preferably at least 140 K.
  • the LC medium according to the present invention preferably has a negative dielectric anisotropy ⁇ from -0.5 to -10, most preferably from -2.5 to -7.5, at 20°C and 1 kHz.
  • the LC medium according to the present invention preferably has a birefringence ⁇ >0.20, very preferably >0.22.
  • 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 compounds of the formula CY and/or PY and TO with one or more compounds of the above-mentioned preferred embodiments and/or with further LC compounds and/or additives, like polymerisable compounds, dyes and/or photoinitiators.
  • the desired amount of the components used in the smaller 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 LC medium according to the invention is preferably used in a device for the homogeneous regulation of the passage of light through an area element, in particular for the regulation of the passage of sunlight (above and below also referred to as "switching device").
  • the said device is preferably employed in a switchable window.
  • Homogeneous regulation here is taken to mean that the transmission is substantially the same at all points within the area element.
  • the invention thus relates to a device for the homogeneous regulation of the passage of light through an area element, where the device contains the mixture according to the invention.
  • the area element here preferably has a dimension of at least 0.05 m 2 , particularly preferably at least 0.1 m 2 , especially preferably at least 0.5 m 2 and very particularly preferably at least 0.8 m 2 .
  • the device for the regulation of the passage of light through an area element preferably comprises the mixture in the form of a layer.
  • This layer is preferably switchable, i.e. represents a switching layer.
  • the switching layer preferably has a thickness of 10 to 100 ⁇ m, very preferably of 12 to 30 ⁇ m and most preferably of 15 to 25 ⁇ m.
  • the device according to the invention is preferably suitable for the regulation of the passage of light in the form of sunlight from the environment into a space.
  • the space here can be any desired space that is substantially sealed off from the environment, for example a building, a vehicle or a container.
  • the device can generally be used for any desired spaces, particularly if these have only limited exchange of air with the environment and have light- transmitting boundary surfaces through which the entry of energy from the outside in the form of light energy can take place.
  • the device is particularly preferably used for spaces which are subjected to strong insolation through light-transmitting areas, for example through window areas. Examples thereof are spaces having large window areas to the outside and the insides of motor vehicles, in particular of automobiles.
  • the device according to the invention is preferably arranged in an opening of a relatively large two-dimensional structure, where the two-dimensional structure itself only allows little passage of light or none at all, and where the opening transmits light to a greater extent in relative terms.
  • the two- dimensional structure is preferably a wall or another delimitation of a space from the outside.
  • the device according to the invention is switchable. Switching here is taken to mean a change in the passage of light through the device.
  • the device according to the invention is preferably electrically switchable.
  • it preferably comprises two or more electrodes, which are installed on both sides of the layer comprising the mixture according to the invention.
  • the electrodes preferably consist of ITO or a thin, preferably transparent metal and/or metal-oxide layer, for example silver or FTO (fluorine-doped tin oxide), or an alternative material known to the person skilled in the art for this use.
  • the ITO electrodes may be provided with a passivation layer, for example comprising SiO 2 .
  • the electrodes are preferably provided with electrical connections.
  • the voltage is preferably provided by a battery, a rechargeable battery or an external power supply.
  • the switching operation takes place through alignment of the molecules of the mixture in the LC state by application of voltage.
  • the device is converted from a state having low absorption, i.e. high light transmissivity, which is present without voltage, into a state having higher absorption, i.e. lower light transmissivity, by application of a voltage.
  • the device is converted from a state having high absorption, i.e. low light transmissivity, which is present without voltage, into a state having lower absorption, i.e. higher light transmissivity, by application of a voltage.
  • the LC medium in the switching layer of the device is preferably nematically LC in both states.
  • the voltage-free state is preferably characterised in that the molecules of the LC medium in the LC state, and thus the molecules of the dye in case a dye is present, are aligned parallel to the plane of the switching layer. This is preferably achieved by a correspondingly selected alignment layer. They are particularly preferably in a twisted nematic state parallel to the plane of the switching layer.
  • the twist angle is preferably less than one complete revolution, particularly preferably between 30 and 270°, very particularly preferably between 100° and 260°, even more preferably between 160 and 255° and most preferably between 230 and 250°.
  • the state under voltage is preferably characterised in that the molecules of the mixture in the LC state, and thus the molecules of the dye, are perpendicular to the plane of the switching layer.
  • the device can be operated without an external power supply by providing the energy required by means of a solar cell or another device for the conversion of light and/or heat energy into electrical energy which is connected to the device.
  • the provision of the energy by means of the solar cell can take place directly or indirectly, i.e. via a battery or rechargeable battery or other unit for the storage of energy connected in-between.
  • the solar cell is preferably installed on the outside of the device or is an internal component of the device, as disclosed, for example, in WO 2009/141295.
  • the device according to the invention preferably has the following layer sequence, from the outside inward, and where further layers may additionally be present.
  • the layers indicated below are preferably directly adjacent to one another in the device:
  • an outer substrate layer preferably made of glass or polymer
  • an outer electrically conductive transparent layer preferably made of ITO
  • an inner electrically conductive transparent layer preferably made of ITO
  • an inner substrate layer preferably made of glass or polymer.
  • the outer and inner substrate layers may consist of glass or of a polymer, preferably a light-transmitting polymer, in particular of glass, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyvinylbutyral (PVB), polymethyl methacrylate (PMMA), polycarbonate (PC), polyimide (PI), COP (cyclic olefin polymers) or TAC (triacetylcellulose).
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PVB polyvinylbutyral
  • PMMA polymethyl methacrylate
  • PC polycarbonate
  • PI polyimide
  • COP cyclic olefin polymers
  • TAC triacetylcellulose
  • the outer and inner electrically conductive layers may consist of electrically conductive transparent oxides (TCO), preferably ITO or SnO2:F, or of a thin transparent metal and/or metal oxide layer, for example of silver.
  • TCO electrically conductive transparent oxides
  • the outer and inner electrically conductive layers are preferably provided with electrical connections.
  • the voltage supply is preferably provided by a battery, a rechargeable battery, a supercapacitor or an external current source.
  • the switching layer preferably has a thickness from 1 ⁇ m to 100 ⁇ m, very preferably from 10 ⁇ m to 100 ⁇ m, more preferably from 12-30 ⁇ m, most preferably from 15 to 25 ⁇ m. This applies in the case where the switching element according to the invention has precisely one switching layer. If the switching element has a plurality of switching layers S which are arranged one after the other, the sum of the thicknesses of these layers is preferably from 5-200 ⁇ m, very preferably from 10-100 ⁇ m.
  • the switching layer has a thickness from 10 ⁇ m to 100 ⁇ m, preferably a thickness from 15 to 25 ⁇ m, a total
  • the switching layer has a diffusive transmission of Td from 0.25 to 1 , very preferably from 0.30 to 1 , more preferably from 0.35 to 1 , and most preferably from 0.40 to 1 , in one of the switching states, preferably in the presence of a voltage.
  • the switching layer has a diffusive haze H ⁇ 5% in another switching state, preferably the voltage-free state, where a diffusive haze H ⁇ 3% is particularly preferred.
  • the non-scattering state preferably occurs without an applied voltage, and the scattering state preferably occurs at voltages in the range from 5 to 200 V, particularly preferably between 20 and 100 V.
  • the switching layer provides an opaque scattering switching state with a value of the haze H from 25 to 100 %, preferably from 60 to 100 %, more preferably from 70 to 100 % and most preferably from 80 to 100 %.
  • the switching layer preferably scatters less than 45%, particularly preferably less than 20%, more preferably less than 10% and very particularly preferably less than 5% of the parallel light rays in backwards scattering directions D(>) from the upper switching layer plane USLP in one of the switching states.
  • This low backwards scattering is particularly preferably present in all of the switching states of the switching layer, in particular also in the scattering switching state of the switching layer.
  • the switching layer has a range of control of the total transmission within a total transmission range from 0% to 80%, where the range of control is at least 15%.
  • the switching layer may be present in a multiswitching layer device together with further switching layers comprising LC medium.
  • the additional switching layers here may be further switching layers S, and/or they may be switching layers which switch from bright to dark without having a scattering switching state. Especial preference is given to multi-switching layer devices
  • switching layers comprising two, three or four switching layers, particularly preferably those comprising two or three switching layers.
  • at least one of these switching layers is a switching layer which has no scattering switching state.
  • the switching element has a second layer sequence on the outer substrate layer of the first layer sequence and/or on the inner substrate layer of the first layer sequence, where the second layer sequence comprises, from the outside inward,
  • the LC medium of the switching layer of the second layer sequence is preferably not forwards-scattering but contains one or more dichroic dyes.
  • the switching layer of the second layer sequence may be a further switching layer, i.e. a switching layer which has a scattering state.
  • the second LC medium contained in the switching layer of the second layer sequence can be an LC medium according to the present invention as described above and below, or a different LC medium.
  • the device according to the invention preferably comprises one or more, particularly preferably two, alignment layers.
  • the alignment layers are preferably directly adjacent to the two sides of the layer comprising the mixture according to the invention.
  • the alignment layers used in the device according to the invention can be any desired layers known to the person skilled in the art for this purpose. Preference is given to polyimide layers, particularly preferably layers comprising rubbed polyimide. Polyimide rubbed in a certain manner known to the person skilled in the art results in alignment of the molecules of the mixture in the LC state in the rubbing direction if the molecules are parallel to the alignment layer (planar alignment). It is preferred here for the molecules of the mixture in the LC state not to be completely planar on the alignment layer, but instead to have a slight pretilt angle. In order to achieve vertical alignment of the molecules to the surface of the alignment layer (homeotropic alignment), polyimide treated in a certain manner is preferably employed as material for the alignment layer (polyimide for very high pretilt angles).
  • polymers obtained by an exposure process with polarised light can be used as alignment layer in order to achieve alignment of the molecules in accordance with an alignment axis (photoalignment).
  • the rubbing directions of the two alignment layers which surround the switching layer comprising the mixture according to the invention in the device according to invention preferably include an angle of 30° to 270°.
  • the device is preferably characterised in that it does not contain a polymer- based polariser, particularly preferably does not contain a polariser in the solid material phase and very particularly preferably contains no polariser at all.
  • the device may also contain one or more polarisers.
  • the polarisers in this case are preferably linear polarisers.
  • the present invention encompasses a window element con- taining a switching element of the type described above.
  • the term "window element” means a light-transmitting component of a window, i.e. a glass pane of a single- or multiple-glazed window, which is intended for or equivalent to part of a building wall.
  • the glass pane has a side (outside) facing the incident parallel light rays, and a side (inside) facing away from the incident parallel light rays.
  • the switching element of the type described above may be arranged on the outside or inside of the window element according to the invention.
  • the switching element according to the invention can be employed not only in a window, but also in the inside of rooms, for example in dividing walls between rooms and elements for the separation of individual compartments of rooms.
  • a visual barrier can be generated between the room parts by the privacy achieved by the switching of the switching element from scattering to clear.
  • the switching element of the type described above can be built into a cladding element suspended in front, where the cladding element suspended in front is arranged in front of the outside of the window. Incident parallel light rays are thereby scattered at a greater separation from an observer who is located in a room adjoining the inside of the window. The greater separation increases the probability that light scattered at small scattering angles passes by the observer and consequently does not dazzle him.
  • the device according to the invention furthermore preferably contains an optical waveguide system which transports light to a solar cell or another device for the conversion of light and/or heat energy into electrical energy, preferably as described in WO 2009/141295.
  • the device according to the invention is a com- ponent of a window which can be switched in its light transmission, particularly preferably a window containing at least one glass area, very particularly preferably a window which contains multipane insulating glass.
  • Window here is taken to mean, in particular, a structure in a building which comprises a frame and at least one glass pane surrounded by this frame. It preferably comprises a heat-insulating frame and two or more glass panes (multipane insulating glass).
  • the device according to the invention is applied directly to a glass area of a window, particularly preferably in the interspace between two glass panes of multipane insulating glass.
  • Tabel A shows preferred compounds which can be used in the LC medium.
  • 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
  • LC media which comprise at least one, two, three, four or more compounds from Table A.
  • Table B indicates possible dopants which can be added to the LC media according to the invention.
  • the Lc media preferably comprise 0-10% by weight, in particular 0.001 -5% by weight and particularly preferably 0.001 -3% by weight, of dopants.
  • Stabilisers which can be added, for example, to the LC media accord the invention in amounts of 0-10% by weight are mentioned below.
  • Table D shows illustrative reactive mesogenic compounds which can be used in the LC media in accordance with the present invention.
  • the LC media according to the invention comprise one or more polymerisable compounds, preferably selected from the polymerisable compounds of the formulae RM-1 to RM-131 .
  • polymerisable compounds preferably selected from the polymerisable compounds of the formulae RM-1 to RM-131 .
  • compounds RM-1 , RM-4, RM-8, RM-17, RM-19, RM-35, RM-37, RM-43, RM- 47, RM-49, RM-51 , RM-59, RM-69, RM-71 , RM-83, RM-97, RM-98, RM-104, RM-1 12, RM-1 15 and RM-1 16 are particularly preferred. Examples
  • Measurement methods The measurements of the measurement quantities used in the present invention are carried out in a Perkin Elmer Lambda 1050 UVA/IS/NIR spectrometer with 150 mm integration sphere (Ulbricht sphere). The values for the transmission intensities are in each case determined averaged over the spectral region from 380 to 780 nm. "Averaged” here is taken to mean numerically averaged.
  • the sample For measurement of the intensity of large-angle scattering l> 2.5°, the sample is mounted directly on the sample holder of the integration sphere. The integration sphere is opened. Exiting light is collected in a light trap, i.e. in a non- reflective black medium, for example in a black, non-reflective cloth, so that light having an aperture angle less than 2.5° leaves the sphere and no longer enters the measurement.
  • a light trap i.e. in a non- reflective black medium, for example in a black, non-reflective cloth
  • the sample is mounted directly on the sample holder at the entrance of the integration sphere.
  • the integration sphere (Ulbricht sphere) is closed and guides all light passing through the sample, i.e. both unscattered and also scattered light, to the detector. Measurements are made with or without driving voltage at the switching medium, in order to obtain the characteristic intensities in different switching states. For a full characterisation, intensity versus voltage curves are measured.
  • the sample is mounted at the opened exit aperture of the integration sphere.
  • a light trap is located in the further light path behind the sample. Light reflected by the sample reaches the detector via the integration sphere and is measured. Non-reflected light leaves the integration sphere without reaching the detector.
  • Td Free from scattering below is intended to mean a value of Td of less than 0.03, preferably less than 0.01 . In practical embodiments a value of Td equal to zero will never be fully achievable.
  • the nematic LC host mixture N1 is formulated as follows.
  • Polymerisable mixtures are formed by adding monomer M1 and a
  • the polymerisable mixtures are suitable for use in switching devices and switchable windows.
  • the polymerisable mixtures are homogenised and filled into test cells consisting of two plane paralle glass substrates that are spaced apart at a cell thickness d ⁇ 10.0 ⁇ m and are each equipped with a transparent ITO electrode and a vertical alignment layer.
  • the LC mixture shows a spontaneous homeotropic (vertical) orientation with respect to the surface of the substrates.
  • test cells are then exposed to UV radiation from a high pressure mercury lamp (Toshiba TUSCURE753) with a cut filter which blocks the radiation shorter than a wavelength of 320 nm and a radiation intensity of 200 mW/cm 2 for 50 seconds, leading to polymerisation of the polymerisable monomer.
  • a high pressure mercury lamp Toshiba TUSCURE753
  • the resulting switching devices can be reversibly switched from the clear to the hazy state, even at high temperatures, by applying a voltage to the electrodes.
  • Fig. 1 shows the switching curve (transmission vs. voltage graph) measured by Otsuka Electronics LCD-5200 for switching devices containing a polymerisable mixture of Example 3 or 4, respectively.
  • the graph indicates high initial transmission (i.e. low initial haze), a switching operation between about 15-30V for the mixture of Example 3, and between about 50-70V for the mixture of Example 4, and a low level of transmission (high level of maximum haze) at higher voltages.
  • the switching operation is highly reversible.

Abstract

La présente invention se rapporte à un milieu à cristaux liquides (LC) comprenant un composé polymérisable, à un procédé pour sa préparation, à son utilisation à des fins optiques, électro-optiques et électroniques, en particulier dans un dispositif de commutation pour l'ajustement du passage de lumière à travers un élément de surface, comme une fenêtre commutable.
PCT/EP2018/061784 2017-05-11 2018-05-08 Milieu à cristaux liquides WO2018206538A1 (fr)

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GB2602924B (en) * 2019-09-09 2024-02-14 Merck Patent Gmbh Liquid-crystal media and PNLC light modulation element

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WO2020127141A1 (fr) * 2018-12-19 2020-06-25 Merck Patent Gmbh Couches de commutation destinées à être utilisées dans un élément de commutation
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