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WO2024189051A1 - Milieu à cristaux liquides - Google Patents

Milieu à cristaux liquides Download PDF

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Publication number
WO2024189051A1
WO2024189051A1 PCT/EP2024/056602 EP2024056602W WO2024189051A1 WO 2024189051 A1 WO2024189051 A1 WO 2024189051A1 EP 2024056602 W EP2024056602 W EP 2024056602W WO 2024189051 A1 WO2024189051 A1 WO 2024189051A1
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compounds
atoms
mixture
formula
another
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Sven Christian Laut
Hee-Kyu Lee
Minghui Yang
Jing Wang
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Merck Patent GmbH
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Merck Patent GmbH
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Priority to CN202480019282.1A priority Critical patent/CN120917124A/zh
Publication of WO2024189051A1 publication Critical patent/WO2024189051A1/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
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—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
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
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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
    • C09K19/062—Non-steroidal liquid crystal compounds containing one non-condensed benzene ring
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • 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
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/122—Ph-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/123—Ph-Ph-Ph
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3004—Cy-Cy
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/301—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
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3016—Cy-Ph-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene

Definitions

  • the present invention relates to a liquid-crystal (LC) medium based on a mixture of polar compounds, to its use for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the fringe-field switching mode, to an LC display of the fringe-field switching mode comprising the LC medium, especially an energy-saving LC display, to a process of preparing the LC medium, and to a process of manufacturing the LC display.
  • LCD liquid-crystal display
  • TN twisted nematic
  • TN LCDs have the disadvantage of a strong viewing-angle dependence of the contrast.
  • FFS far-field switching
  • FFS displays usually contain an LC medium with positive dielectric anisotropy, and an alignment layer, usually of polyimide, which provides planar alignment to the molecules of the LC medium.
  • FFS displays can be operated as active-matrix or passive-matrix displays.
  • active-matrix displays individual pixels are usually addressed by integrated, non-linear active elements, such as, for example, transistors (for example thin-film transistors (“TFTs”)), while in the case of passive-matrix displays, individual pixels are usually addressed by the multiplex method, as known from the prior art.
  • TFTs thin-film transistors
  • the displays further comprise an alignment layer, preferably of polyimide provided on at least one of the substrates that is in contact with the LC medium and induces planar alignment of the LC molecules of the LC medium.
  • These displays require an LC medium with high reliability.
  • so-called VA (“vertically aligned”) displays are known which have a broad viewing angle and fast response times.
  • the LC cell of a VA display contains a layer of an LC medium between two transparent electrodes, where the LC medium usually has a negative value of the dielectric anisotropy ( ⁇ ⁇ ). In the switched-off state, the molecules of the LC layer are aligned perpendicular to the electrode surfaces (homeotropically) or have a tilted homeotropic alignment.
  • IPS in-plane switching
  • VA in-plane switching
  • VA displays having tilt domains have, compared with conventional VA displays, a greater viewing-angle independence of the contrast and the grey shades.
  • displays of this type are simpler to produce since additional treatment of the electrode surface for uniform alignment of the molecules in the switched-on state, such as, for example, by rubbing, is no longer necessary.
  • the preferential direction of the tilt or pretilt angle is controlled by a special design of the electrodes.
  • the use of LC media with negative dielectric anisotropy in VA or FFS displays has also several drawbacks. For example, they have a significantly lower reliability compared to LC media with positive dielectric anisotropy.
  • the term "reliability” as used hereinafter means the quality of the performance of the display during time and with different stress loads, such as light load, temperature, humidity, or voltage which cause display defects such as image sticking (area and line image sticking), mura, yogore etc. and which are known to the skilled person in the field of LC displays.
  • VHR voltage holding ration
  • the reduced reliability of an LC medium with negative dielectric anisotropy in a VA or FFS display can be explained by an interaction of the LC molecules with the polyimide of the alignment layer, as a result of which ions are extracted from the polyimide alignment layer, and wherein LC molecules with negative dielectric anisotropy do more effectively extract such ions.
  • the LC medium has to show a high reliability and a high VHR value after UV exposure. Further requirements are a high specific resistance, a large working- temperature range, short response times even at low temperatures, a low threshold voltage, a multiplicity of grey levels, high contrast and a broad viewing angle, and reduced image sticking.
  • a further object of the invention is to provide FFS-, VA-, and IPS- displays with high contrast ratio, good transmission, high reliability, a VHR value especially after backlight exposure, a high specific resistance, a large working-temperature range, short response times even at low temperatures, a low threshold voltage, a multiplicity of grey levels, high contrast and a broad viewing angle, and reduced image sticking.
  • the contrast ratio is defined as the ratio of the luminance of the brightest shade (white) to that of the darkest shade (black) that the system is capable of producing, i.e., the transmittane (white level) to the scattering parameter (dark level).
  • the contrast ratio can be significantly improved by the lower scattering parameter (high Kavg). Therefore, a LC mixture having high Kavg is very effective to achieve a high contrast ratio display.
  • a further object of the present invention is to provide LC mixtures with a favourably high average elastic constant Kavg, which contributes to a high contrast ratio. It was found that one or more of these objects could be achieved by providing an LC medium as disclosed and claimed hereinafter.
  • Preferred compounds of the formulae IA, IB, IC and ID are those wherein R 12 denotes an alkyl or alkoxy radical having 1 to 15 C atoms, and very preferably denotes (O)CvH2v+1 wherein (O) is an oxygen atom or a single bond and v is 1, 2, 3, 4, 5 or 6.
  • LC medium comprises one or more compounds of the formula IA 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 denotes a straight-chain alkenyl radical having 2-6 C atoms
  • (O) denotes an oxygen atom or a single bond
  • Particularly preferred LC media according to the invention comprise one or more compounds selected from the group consisting of formulae IA-2, IA-4, IA-6, IA-8, IA-10, IA-22, IA-23, IA-24, IA-25 and IA-32 to IA-36.
  • the LC medium comprises one or more compounds of the formula IA-2 selected from the following subformulae:
  • the LC medium comprises one or more compounds of the following formulae:
  • the LC medium comprises one or more compounds of the formula IA- 6 selected from the following sub-formulae:
  • the LC medium comprises one or more compounds of the following formulae:
  • Preferred LC media additionally comprise one or more compounds of formula IA-0 in which R 11 and R 12 have one of the meanings given in formula IA above.
  • Preferred compounds of the formula IA-0 are selected from the group consisting of the following subformulae in which, Alkyl and Alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, Alkoxy and Alkoxy* each, independently of one another, denote a straight-chain alkoxy radical having 1-6 C atoms, Alkenyl and Alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms, and O denotes an oxygen atom or a single bond.
  • Particularly preferred compounds of the formula IA-0 are selected from the group consisting of subformula IA-0-6, in which Alkoxy has the meanings defined above and preferably denotes methoxy, ethoxy, n- propyloxy, n-butyloxy or n-pentyloxy.
  • the LC medium comprises one or more compounds of the formula IB 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 denotes a straight-chain alkenyl radical having 2-6 C atoms
  • (O) denotes an oxygen atom or a single bond
  • LC media comprise one or more compounds selected from the group consisting of formulae IB-2, IB-6 and IB-8.
  • the LC medium comprises one or more compounds of the formula IB-6 selected from the following sub-formulae:
  • the LC medium comprises one or more compounds of the following formulae:
  • the LC medium comprises one or more compounds of the formula IC selected from the formula IC-1, in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, preferably in amounts of 0.5% to 5 % by weight, in particular 1% to 3 % by weight.
  • the LC medium comprises one or more compounds of the formula ID 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 denotes a straight-chain alkenyl radical having 2-6 C atoms
  • (O) denotes an oxygen atom or a single bond
  • Y denotes H or CH 3
  • Particularly preferred LC media according to the invention comprise one or more compounds of the formula ID-1 and/or ID-2.
  • Very preferred compounds of the formula ID are compounds of the formula ID-5 selected from the following subformulae,
  • the LC medium comprises one or more compounds of formula ID-5a in which R 11 , Y and q have the meanings given in formula ID, and R 13 is , in which r is 0, 1, 2, 3, 4, 5 or 6 and s is 1, 2 or 3.
  • Preferred compounds of formula IID-5a are selected from the following subformulae:
  • Particularly preferred LC media according to the invention comprise one or more compounds selected from the group consisting of formulae IE-1, IE-2, IE-3, IE-4, IE-5.
  • the proportion of compounds of the formulae IA and/or IB in the mixture as a whole is preferably at least 20 % by weight.
  • Particularly preferred LC media according to the invention comprise one or more compounds selected from the formulae IA-2, IA-4, IA-6, IA-8, I-10, IA-22, IA-23, IA-24, IA-25, IB-2, IB-6, IB-8, IC-1, ID-2, ID-5, IE-1, IE-2, IE-3, IE-4, IE-5, or their subformulae.
  • the invention further relates to the use of the LC medium as described above and below in LC displays, preferably in LC displays of the VA, IPS, FFS, UB-FFS or UBplus mode.
  • the invention furthermore relates to a process for preparing an LC medium as described above and below, comprising the steps of mixing one or more compounds of formula I with one or more compounds as described below and optionally with further LC compounds and/or additives.
  • the invention furthermore relates to an LC display comprising an LC medium according to the invention as described above and below, preferably an LC display of the VA, IPS, FFS, UB-FFS or UBplus mode.
  • the invention furthermore relates to a process for manufacturing an LC display as described above and below, comprising the steps of filling or otherwise providing an LC medium as described above and below between the substrates of the display.
  • the LC media according to the present invention allow to achieve one or more of the following advantageous effects: - a favourably high average elastic constant Kavg that equals to (K1+K2+K3)/3, which contributes to a high contrast ratio, - a favourably low ratio of rotational viscosity to the splay elastic constant ⁇ 1 / K 11 , which contributes to improved switching behaviour especially at low driving voltages and is useful to enable energy-saving displays.
  • the LC media according to the present invention show one or more of the following advantageous properties when used in LC displays: - high contrast ratio, - high transmittance, - reduced rotational viscosity, - fast response times, - a low threshold voltage which is useful to enable energy-saving displays.
  • the LC media according to the present invention show a favourable combination of low rotational viscosity and high average elastic constant Kavg.
  • a low rotational viscosity and therefore the low ratio of rotational viscosity to the splay elastic constant ⁇ 1 / K 11 improves switching behaviour especially at low driving voltages.
  • an increased Kavg enables the realisation of a low scattering parameter and thereby a high contrast ratio.
  • the LC media according to the present invention show high VHR values and less or no undesired mura effects such as edge mura.
  • denotes a trans-1,4-cyclohexylene ring denotes a 1,4-phenylene ring.
  • the single bond shown between the two ring atoms can be attached to any free position of the benzene ring.
  • a terminal group like R 11,12 , R 21,22 , R 31, 32, 33 , R 41,42 , R 51,52 , R 61 , R 71 , R N1,N2 , R 81,82 , R 91,92,93 , R L1,L2 , R Q , R R1 ,R2 , or L denotes an alkyl radical and/or an alkoxy radical, this may be straight-chain or branched.
  • It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.
  • one of the aforementioned terminal groups denotes an alkyl radical wherein one or more CH 2 groups are replaced by S, this may be straight-chain or branched. It is preferably straight-chain, has 1, 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes thiomethyl, thioethyl, thiopropyl, thiobutyl, thiopentyl, thiohexyl or thioheptyl.
  • one of the aforementioned terminal groups denotes an alkyl or alkenyl radical which is at least monosubstituted by halogen
  • this radical is preferably straight-chain, and halogen is preferably F or Cl.
  • halogen is preferably F.
  • the resultant radicals also include perfluorinated radicals.
  • the fluorine or chlorine substituent may be in any desired position, but is preferably in the ⁇ -position.
  • one or more of the aforementioned terminal groups are selected from the group consisting of -S 1 -F, -O-S 1 -F, -O-S 1 -O-S 2 , wherein S 1 is C 1-12 -alkylene or C 2-12 -alkenylene and S 2 is H, C 1-12 -alkyl or C 2-12 -alkenyl, and very preferably are selected from the group consisting of Halogen is preferably F or Cl, very preferably F.
  • substituents L are, for example, F, Cl, CN, NO 2 , CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , COCH 3 , COC 2 H 5 , COOCH 3 , COOC 2 H 5 , CF 3 , OCF 3 , OCHF 2 , OC 2 F 5 , furthermore phenyl. in which L has one of the meanings indicated above.
  • Further preferred embodiments of the LC medium according to the present invention are listed below, including any combination thereof.
  • the LC medium further comprises one or more compounds of formula II,
  • Preferred compounds of the formulae IIA, IIB, IIC, IID and IIE are those wherein R 22 denotes an alkyl or alkoxy radical having up to 15 C atoms, and very preferably denotes (O)CvH2v+1, wherein (O) is an oxygen atom or a single bond and v is 1, 2, 3, 4, 5 or 6.
  • LC medium comprises one or more compounds of the formula IIA selected from the group consisting of the following 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
  • LC media comprise one or more compounds selected from the group consisting of formulae IIA-2, IIA-8, IIA-10, IIA-16, IIA-18, IIA-40, IIA-41, IIA-42 and IIA-43.
  • the LC medium comprises one or more compounds of the formula IIA-2 selected from the following subformulae:
  • the LC medium comprises one or more compounds of the following formulae:
  • the LC medium comprises one or more compounds of the formula IIA-10 selected from the following sub-formulae:
  • the LC medium comprises one or more compounds of the following formulae:
  • Preferred LC media additionally comprise one or more compounds of formula IIA-Y in which R 21 and R 22 have one of the meanings given in formula IIA above, and L 1 and L 2 , identically or differently, denote F or Cl.
  • Preferred compounds of the formula IIA-Y are selected from the group consisting of the following subformulae in which, Alkyl and Alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, Alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms, Alkenyl and Alkenyl* each, independently of one another, denote a straight- chain alkenyl radical having 2-6 C atoms, and O denotes an oxygen atom or a single bond.
  • Particularly preferred compounds of the formula IIA-Y are selected from the group consisting of following subformulae: in which Alkoxy and Alkoxy* have the meanings defined above and preferably denote methoxy, ethoxy, n-propyloxy, n-butyloxy or n-pentyloxy.
  • the LC medium comprises one or more compounds of the formula IIB selected from the group consisting of formulae IIB-1 to IIB-30,
  • 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
  • LC media comprise one or more compounds selected from the group consisting of formulae IIB-2, IIB-10 and IIB-16.
  • the LC medium comprises one or more compounds of the formula IIB-10 selected from the following sub-formulae:
  • the LC medium comprises one or more compounds of the formulae IIB-10a-1 to IIB- 10a-5:
  • the LC medium comprises one or more compounds of the formula IIC selected from the formula IIC-1, in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, preferably in amounts of 0.5% to 5 % by weight, in particular 1% to 3 % by weight.
  • Particularly preferred LC media according to the invention comprise one or more compounds of the formula IID-1 and/or IID-4. Very preferred compounds of the formula IID are selected from the following subformulae of IID-1
  • the LC medium comprises one or more compounds of formula IID-14a in which R 21 , Y and q have the meanings given in formula IID, and R 23 is , in which r is 0, 1, 2, 3, 4, 5 or 6 and s is 1, 2 or 3.
  • Preferred compounds of formula IID-14a are the compounds IID-14a-1 to IID-14a-14: Very preferred compounds of the formula IID are selected from the following subformulae of IID-17, wherein v is 1, 2, 3, 4, 5 or 6.
  • Particularly preferred LC media according to the invention comprise one or more compounds selected from the group consisting of formulae IIE-2, IIE-8, IIE-10, IIE-16, IIE-18, IIE-37, IIE-38, IIE-39 and IIE-40.
  • the LC medium comprises one or more compounds of the formula IIE-2 selected from the following sub-formulae:
  • the LC medium comprises one or more compounds of the formula IIE-10 selected from the following sub-formulae:
  • Particularly preferred LC media according to the invention comprise one or more compounds selected from the formulae IIA-2, IIA-8, IIA-10, IIA-16, IIA-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1, IID-4, IID-10, IIE-2, IIE-8, IIE-10, IIE-16, IIE-18, IIE-37, IIE-38, IIE-39, and IIE-40 or their subformulae.
  • R 31 and R 32 each, independently of one another, denote H, an alkyl, alkoxy or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by F, Cl, CN or CF 3 or at least monosubstituted by halogen, where, in addition, one or more CH 2 groups in these radicals may be replaced by -O-, -S-,
  • Y 1 , Y 2 H, F, Cl, CF 3 , CHF 2 , CH 3 or OCH 3 preferably H, CH 3 or OCH 3 , very preferably H,
  • R 31 and R 32 are preferably selected from straight-chain alkyl or alkoxy with 1 to 12, preferably 1 to 7 C atoms, straight-chain alkenyl with 2 to 12, preferably 2 to 7 C atoms and cyclic alkyl or alkoxy with 3 to 12, preferably 3 to 8 C atoms.
  • the LC medium comprises one or more compounds of formula III selected from the subformulae III-1 to III-6:
  • R 31 and R 32 each, independently of one another, denote an alkyl, alkenyl or alkoxy radical having up to 15 C atoms, preferably having 1 to 7 C atoms, more preferably one or both of them denote an alkoxy radical; or cyclic alkyl having 3 to 6 C atoms, R 33 denotes alkyl or alkenyl having up to 7 C atoms or a group Cy-C n H 2n+1 -, m and n are, identically or differently, 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, Cy denotes a cycloaliphatic group having 3, 4 or 5 ring atoms, which is optionally substituted with alkyl or alkenyl each having up to 3 C atoms, or with halogen or CN, and preferably denotes cyclopropyl, cyclobutyl, cyclopentyl or cyclopenten
  • alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms
  • alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms
  • alkoxy and alkoxy* each, independently of one another, denote a straight-chain alkoxy radical having 1-6 C atoms
  • L 31 and L 32 each, independently of one another, denote F or Cl, preferably both F.
  • Very preferred compounds of formula III-1-1 are selected from the group consisting of the following subformulae,
  • alkoxy denotes a straight-chain alkoxy radical having 1, 2, 3 or 4 C atoms.
  • Very preferred compounds of the formula III-2 are the following,
  • alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms, preferably ethoxy, propoxy, butoxy or pentoxy, very preferably ethoxy or propoxy.
  • Very preferred compounds of formula III-6 are selected from the group consisting of the following formulae, in which R 32 denotes alkyl having 1 to 7 C-atoms, preferably ethyl, n-propyl or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl or alternatively – (CH 2 ) n F in which n is 2,3,4, or 5, preferably C 2 H 4 F.
  • Preferred compounds of formula III is III-1-1-3, III-1-1-4, III-1-1-5 as well as III-6-2, and the most preferred are compounds B(S)-2O-O4, B(S)-2O-O5, B(S)-2O-O6, and COB(S)-2- O4.
  • the LC medium comprises one or more compounds of formula IIIA selected from the subformulae IIIA-1 to IIIA-6: in which the occurring groups have the same meanings as given under formula III above and preferably R 31 and R 32 each, independently of one another, denote an alkyl, alkenyl or alkoxy radical having up to 15 C atoms, preferably having 1 to 7 C atoms, more preferably one or both of them denote an alkoxy radical; or cyclic alkyl having 3 to 6 C atoms, R 33 denotes alkyl or alkenyl having up to 7 C atoms or a group Cy-C n H 2n+1 -, m and n are, identically or differently, 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, Cy denotes a cycloaliphatic group having 3, 4 or 5 ring atoms, which is optionally substituted with alkyl or alkenyl each having up to 3 C atoms, or with
  • Preferred compounds of formula IIIA are those of formula IIIA-1: in which the occurring groups have the same meanings as given under formula IIIA above and preferably R 31 and R 32 each, independently of one another, an alkyl, alkenyl or alkoxy radical having up to 15 C atoms, preferably having 1 to 7 C atoms, more preferably one or both of them denote an alkoxy radical and L 31 and L 32 each, independently of one another, denote F or Cl, preferably both denote F.
  • the LC medium comprises one or more compounds of the formula IIIA-1 selected from the group of compounds of formulae IIIA-1-1 to IIIA-1- 10, preferably of formula IIIA-1-6,
  • alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms
  • alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms
  • alkoxy and alkoxy* each, independently of one another, denote a straight-chain alkoxy radical having 1-6 C atoms
  • L 31 and L 32 each, independently of one another, denote F or Cl, preferably both F.
  • the LC medium comprises one or more compounds of the formula IV, in which R 41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms where, in addition, one or more CH 2 groups may be replaced by or an unsubstituted alkenyl radical having 2 to 7 C atoms, preferably an n-alkyl radical, particularly preferably having 2, 3, 4 or 5 C atoms, and R 42 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkoxy radical having 1 to 6 C atoms, both preferably having 2 to 5 C atoms, or an unsubstituted alkenyl radical having 2 to 7 C atoms, preferably having 2, 3 or 4 C atoms, more preferably a vinyl radical or a 1-propenyl radical and in particular a vinyl radical.
  • R 41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms where, in addition, one or more CH 2
  • the compounds of the formula IV are preferably selected from the group of the compounds of the formulae IV-1 to IV-4, in which alkyl and alkyl’, independently of one another, denote alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, alkenyl denotes an alkenyl radical having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably 2 C atoms, alkenyl’ denotes an alkenyl radical having 2 to 5 C atoms, preferably having 2 to 4 C atoms, particularly preferably having 2 to 3 C atoms, and alkoxy denotes alkoxy having 1 to 5 C atoms, preferably having 2 to 4 C atoms.
  • the LC medium comprises one or more compounds selected from the compounds of the formulae IV-1-1 to IV-1-6:
  • the LC medium according to the invention comprises one or more compounds of the formulae IV-2-1 and/or IV-2-2
  • the LC medium according to the invention comprises a compound of formula IV-3, in particular selected from the compounds of the following subformulae:
  • the LC medium according to the invention preferably comprises one or more compounds CC-n-V and/or CC-n-Vm, in particular CC-3-V, CC-4-V, CC-3-V1 and/or CC-4-V1, preferably in a total concentration in the range of from 15 to 60 %, preferably from 18 to 52 %.
  • CC-3-V is preferably used in concentrations of 5-50 %, in particular 6-45 %.
  • the LC medium according to the invention comprises one or more compounds of formula IV-3 selected from the compounds of the following subformulae: in which alkyl denotes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or n-pentyl.
  • the LC medium according to the invention comprises a compound of formula IV-4, in particular selected from the compounds of the following formulae:
  • the LC medium comprises one or more compounds of formula IV-4 and its subformulae in which one or both of "alkenyl” and “alkenyl' " denote in which m is 0, 1 or 2, and n is 0, 1 or 2, very preferably selected from compounds of formulae IV-4-3 to IV-4-6.
  • the LC medium according to the invention comprises one or more compounds of the formula IV-1 or its subformulae and/or one or more compounds of the formula IV-3 or its subformulae and/or one or more compounds of the formula IV-4 or its subformulae, where the total concentration of these compounds of the formula IV-1 is in the range from 1% to 30%.
  • the LC medium according to the invention preferably comprises at least one compound of the formula IVa-1and/or formula IVa-2.
  • the proportion of compounds of the formula IVa in the mixture as a whole is preferably at least 5 % by weight
  • the LC medium comprises one or more compounds of formula IVb-1 to IVb- 3 in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1 to 6 C atoms, and alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2 to 6 C atoms.
  • the proportion of the compounds of the formulae IV-1 to IV-3 in the mixture as a whole is preferably at least 3 % by weight, in particular ⁇ 5 % by weight.
  • the compounds of the formula IVb-2 are particularly preferred.
  • Particularly preferred compounds of the formulae IV-1 to IV-3 are selected from the group consisting of the following formulae in which alkyl* denotes an alkyl radical having 1 to 6 C atoms and preferably denotes n- propyl.
  • the LC medium according to the invention particularly preferably comprises one or more compounds of the formulae IVb-1-1 and/or IVb-2-3.
  • the LC medium according to the invention comprises one or more compounds of formula V in which R 51 and R 52 independently of one another, denote H, an alkyl, alkoxy or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by F, Cl, CN or CF 3 or at least monosubstituted by halogen, where, in addition, one or more CH 2 groups in these radicals may be replaced by -O-, -S-,-C ⁇ C-, -CF 2 O-, -OCF 2 -, -OC-O-, -O-CO- in such a way that O atoms are not linked directly to one another, 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 6 C atoms, preferably n-alkoxy, particularly preferably n-alkoxy
  • LC media comprise one or more compounds of the formulae V-1, V-3, V-4, V- 6, V-7, V-10, V-11, V-12, V-14, V-15, and/or V-16.
  • LC media according to the invention very particularly preferably comprise the compounds of the formula V-10 and/or IV-1, in particular in amounts of 5 to 30 %.
  • Preferred compounds of the formulae V-10 are indicated below:
  • the LC medium according to the invention particularly preferably comprises the tricyclic compounds of the formula V-10a and/or of the formula V-10b in combination with one or more bicyclic compounds of the formulae IV-1
  • the total proportion of the compounds of the formulae V-10a and/or V-10b in combination with one or more compounds selected from the bicyclohexyl compounds of the formula IV-1 is 5 to 40 %, very particularly preferably 15 to 35 %.
  • Particularly preferred LC media comprise the compounds V-10a and/or IV-1-1
  • the compounds V-10a and IV-1-1 are preferably present in the mixture in a concentration of 5 to 30 %, very preferably 10 to 25 %, based on the mixture as a whole.
  • Preferred LC media comprise at least one compound selected from the group of the compounds
  • R 51 , R 52 , R 41 and R 42 have the meanings indicated above.
  • R 51 and R 41 denotes alkyl or alkenyl having 1 to 6 or 2 to 6 C atoms, respectively
  • R 52 and R 42 denotes alkenyl having 2 to 6 C atoms.
  • R 51 denotes alkyl or alkenyl having 1 to 6 or 2 to 6 C atoms
  • R 52 denotes alkyl having 1 to 6 C atoms, or alkoxy having 2 to 6 C atoms.
  • the LC medium according to the invention comprises one or more compounds of the formula V-7, preferably selected from the compounds of the formulae V-7a to V-7e: in which alkyl denotes an alkyl group having 1 to 7 C atoms, alkenyl denotes an alkenyl group having 2 to 7 C atoms, and cycloalkyl denotes a cyclic alkyl group having 3 to 12 C atoms, preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylalkyl, cyclobutylalkyl or cyclopentylalkyl.
  • Very preferred compounds of the formulae V-7a to V-7e are selected from the compounds of the following subformulae:
  • alkyl denotes ethyl, n-propyl, n-butyl or n-pentyl, preferably n-propyl.
  • R 51 and R 52 independently of one another denote straight-chain alkyl having 1 to 7 C atoms or alkenyl having 2 to 7 C atoms.
  • the LC medium additionally comprises one or more compounds of the formulae VI-1 to VI-25, in which R 61 denotes a straight-chain alkyl or alkoxy radical having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms, (O) denotes -O- or a single bond, X denotes F, Cl, OCF 3 or OCHF 2 , L x denotes H or F, m is 0, 1, 2, 3, 4, 5 or 6 and n is 0, 1, 2, 3 or 4.
  • R 61 preferably denotes methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.
  • X preferably denotes F or OCH 3 , very preferably F.
  • the LC medium according to the invention preferably comprises the terphenyls of the formulae VI-1 to VI-25 in amounts of 2 to 30 % by weight, in particular 5 to 20 % by weight. Particular preference is given to compounds of the formulae VI-1, VI-2, VI-4, VI-20, VI- 21, and VI-22 wherein X denotes F.
  • R 61 preferably denotes alkyl, furthermore alkoxy, each having 1 to 5 C atoms.
  • R 61 preferably denotes alkyl or alkenyl, in particular alkyl.
  • R 61 preferably denotes alkyl.
  • X preferably denotes F.
  • the terphenyls of formula VI-1 to VI-25 are preferably employed in the LC media according to the invention if the ⁇ n value of the mixture is to be ⁇ 0.1.
  • Preferred LC media comprise 2 to 20 % by weight of one or more terphenyl compounds selected from the group of the compounds of formulae VI-1 to VI-25.
  • the LC medium additionally comprises one or more compounds of the formulae VII-1 to VII-9 in which R 71 each, independently of one another, have one of the meanings indicated for R 21 in formula IIA, and w and x each, independently of one another, denote 1 to 6. Particular preference is given to LC media comprising at least one compound of the formula VII-9.
  • the LC medium according to the invention preferably comprises the compounds of the formulae BC, CR, PH-1, PH-2 in amounts of 3 to 20 % by weight, in particular in amounts of 3 to 15 % by weight.
  • Particularly preferred compounds of the formulae BC and CR are the compounds BC-1 to BC-7 and CR-1 to CR-5,
  • alkyl and alkyl* each, independently of one another denote a straight-chain alkyl radical having 1 to 6 C atoms
  • alkenyl and alkenyl* each, independently of one another denote a straight-chain alkenyl radical having 2 to 6 C atoms.
  • an LC medium comprising one, two or three compounds of the formula BC-2, BF-1 and/or BF-2.
  • Particularly preferred compounds of the formula BC the compounds B(A)-2O- O2
  • Particularly preferred compounds of the formula PH-1 the compounds B(P)-2O- O3 and B(P)-2O-O4,
  • LC medium comprising one or more indane compounds of the formula In, in which R 91 , R 92 , R 93 each, independently of one another, denote a straight-chain alkyl, alkoxy, alkoxyalkyl or alkenyl radical having 1 to 6 C atoms, R 92 and R 93 may also denote halogen, preferably F, i denotes 0, 1 or 2.
  • Preferred compounds of the formula In are the compounds of the formulae In-1 to In-16 indicated below:
  • LC media comprising one or more compounds of the formulae L-1 to L-8,
  • alkyl denotes an alkyl radical having 1 to 6 C atoms
  • s denotes 1 or 2.
  • the compounds of the formulae L-1 to L8 are preferably employed in concentrations of 5 to 15 % by weight, in particular 5 to 12 % by weight and very particularly preferably 8 to 10 % by weight.
  • LC medium comprising one or more quaterphenyl compounds selected from the following formula: wherein R Q is alkyl, alkoxy, oxaalkyl or alkoxyalkyl having 1 to 9 C atoms or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated, X Q is F, Cl, halogenated alkyl or alkoxy having 1 to 6 C atoms or halogenated alkenyl or alkenyloxy having 2 to 6 C atoms, L Q1 to L Q6 independently of each other are H or F, with at least one of L Q1 to L Q6 being F.
  • Preferred compounds of formula Q are those wherein R Q denotes straight-chain alkyl with 2 to 6 C-atoms, very preferably ethyl, n-propyl or n-butyl. Preferred compounds of formula Q are those wherein L Q3 and L Q4 are F. Further preferred compounds of formula Q are those wherein L Q3 , L Q4 and one or two of L Q1 and L Q2 are F. Preferred compounds of formula Q are those wherein X Q denotes F or OCF 3 , very preferably F.
  • quaterphenyl compounds of formula Q to the LC mixture of a polymerizable LC medium enables to reduce ODF mura, whilst maintaining high UV absorption, enabling quick and complete polymerization, enabling strong and quick tilt angle generation, and increasing the UV stability of the LC medium.
  • compounds of formula Q which have positive dielectric anisotropy
  • to the LC medium with negative dielectric anisotropy allows a better control of the values of the dielectric constants and , and in particular enables to achieve a high value of the dielectric constant while keeping the dielectric anisotropy ⁇ ⁇ constant, thereby reducing the kick-back voltage and reducing image sticking.
  • the LC medium according to the invention preferably comprises - one or more compounds of formula I or its subformulae in a proportion from 1 to 25%, very preferably from 2 to 22 %, most preferably from 2.5 to 20% by weight; and/or - one or more compounds of formula IIA, IIB, and/or IID, preferably in a total concentration in the range of from 20 to 65%, more preferably from 25 to 60%, particularly preferably from 30 to 55%; wherein formula IIA preferably in a total concentration in the range of 5 to 30%; wherein formula IIB preferably in a total concentration in the range of 1 to 5%; wherein formula IID preferably in a total concentration in the range of 10 to 35%; wherein the total concentration of one or more compounds of formula I and IIA is preferably in the range from 10 to 45%, more preferably from 15 to 30%, most preferably from 17 to 28% by weight; wherein the total concentration of one or more compounds of formula I and IID is preferably in the range from 10 to 50%, more preferably from 15
  • the term "threshold voltage” relates to the capacitive threshold (V0), also called the Freedericks threshold, unless explicitly indicated otherwise.
  • the liquid-crystal media according to the invention have high values for the voltage holding ratio in liquid-crystal cells. In general, liquid-crystal media having a low addressing voltage or threshold voltage exhibit a lower voltage holding ratio than those having a higher addressing voltage or threshold voltage and vice versa.
  • dielectrically positive compounds denotes compounds having a ⁇ ⁇ > 1.5
  • dielectrically neutral compounds denotes those having -1.5 ⁇ ⁇ ⁇ ⁇ 1.5
  • dielectrically negative compounds denotes those having ⁇ ⁇ ⁇ -1.5.
  • the dielectric anisotropy of the compounds is determined here by dissolving 10 % of the compounds in a liquid-crystalline host and determining the capacitance of the resultant mixture in at least one test cell in each case having a layer thickness of 20 ⁇ m with homeotropic and with homogeneous surface alignment at 1 kHz.
  • R R1 and R R2 are different from one another, one of these radicals usually being an alkyl or alkoxy group.
  • Other variants of the proposed substituents are also common. Many such substances or also mixtures thereof are commercially available. All these substances can be prepared by methods known from the literature. It goes without saying for the person skilled in the art that the VA, IPS or FFS mixture according to the invention may also comprise compounds in which, for example, H, N, O, Cl and F have been replaced by the corresponding isotopes.
  • the LC medium has preferably a nematic LC phase.
  • the LC media contain one or more chiral dopants, preferably in a concentration from 0.01 to 1% by weight, very preferably from 0.05 to 0.5% by weight.
  • the chiral dopants are preferably selected from the group consisting of compounds from Table C below, very preferably from the group consisting of R- or S- 1011, R- or S-2011, R- or S-3011, R- or S-4011, and R- or S-5011.
  • the LC media contain a racemate of one or more chiral dopants, which are preferably selected from the chiral dopants mentioned in the previous paragraph.
  • the LC media contain one or more further stabilisers.
  • Preferred stabilisers are selected from the compounds of formula H in which Ar denotes an aromatic or heteroaromatic hydrocarbon group having 4 to 40 C atoms, preferably 6 to 30 C atoms; Sp denotes a spacer group; R S denotes H, alkyl having 1 to 12 C atoms or alkenyl having 2 to 12 C atoms; Z S denotes -O-, -C(O)O-, -(CH 2 )z- or –(CH 2 ) z O-, or a single bond; HA denotes R H denotes H, O . , CH 3 , OH or OR S , preferably H or O .
  • R S1 , R S2 , R S3 and R S4 identically or differently, denote alkyl having 1 to 6 C atoms, preferably having 1 to 3 C atoms, very preferably CH 3 ;
  • G denotes H or R S or a group Z S -HA;
  • z is an integer from 1 to 6; and
  • q is 3 or 4.
  • the compounds of formula H are described in EP3354710 A1 and EP3354709 A1.
  • Preferred compounds of formula H are selected from the formulae H-1, H-2 and H-3: in which R H has the meanings given above and preferably denotes H or O .
  • n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7, and Sp denotes a spacer group, preferably alkylene having 1 to 12 C atoms in which one or more non-adjacent - CH 2 - groups may be replaced with -O-.
  • Preferred compounds of formula H-1 are those of formula H-1-1:
  • R H has the meanings given above and preferably denotes H or O .
  • n is an integer from 0 to 12, preferably 5, 6, 7, 8 or 9, very preferably 7.
  • Very preferred compounds of formula H-1-1 are those of formula H-1-1-1:
  • Preferred compounds of formula H-2 are those of formula H-2-1:
  • R H has the meanings given above and preferably denotes H or O .
  • n2 on each occurrence identically or differently, preferably identically, is an integer from 1 to 12, preferably 2, 3, 4, 5, or 6, very preferably 3, and R S on each occurrence identically or differently, preferably identically, denotes alkyl having 1 to 6 C atoms, preferably n- butyl.
  • Very preferred compounds of formula H-2-1 are those of formula H-2-1-1:
  • Preferred compounds of formula H-3 are selected from the formula H-3-1:
  • n preferably denotes 3.
  • n preferably denotes 7.
  • Very preferred stabilisers are selected from the group of the compounds of the formulae ST-2a-1, ST-3a-1, ST-3b-1, ST-8-1, ST-9-1 and ST-12:
  • the LC medium comprises one or more stabilisers selected from Table D below.
  • the proportion of stabilisers in the LC medium is from 10 to 500 ppm, very preferably from 20 to 100 ppm.
  • the LC medium according to the present invention may additionally comprise one or more further components or additives, preferably selected from the list including but not limited to co-monomers, chiral dopants, polymerization initiators, inhibitors, stabilisers, surfactants, wetting agents, lubricating agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, defoaming agents, deaerators, diluents, reactive diluents, auxiliaries, colourants, dyes, pigments and nanoparticles.
  • further components or additives preferably selected from the list including but not limited to co-monomers, chiral dopants, polymerization initiators, inhibitors, stabilisers, surfactants, wetting agents, lubricating agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, defoaming agents, deaerators, diluents, reactive diluents, auxiliaries, colourants, dyes, pigments and nano
  • LC media for example, 0 to 15% by weight of pleochroic dyes, furthermore nanoparticles, conductive salts, preferably ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (cf., for example, Haller et al., Mol. Cryst. Liq. Cryst.24, 249-258 (1973)), for improving the conductivity, or substances for modifying the dielectric anisotropy, the viscosity and/or the alignment of the nematic phases.
  • conductive salts preferably ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (cf., for example, Haller et al., Mol. Cryst. Liq.
  • the LC media which can be used in accordance with the invention are prepared in a manner conventional per se, for example by mixing one or more of the above-mentioned compounds with one or more polymerizable compounds as defined above, and optionally with further liquid-crystalline compounds and/or additives.
  • the desired amount of the components used in lesser amount is dissolved in the components making up the principal constituent, advantageously at elevated temperature. It is also possible to mix solutions of the components in an organic solvent, for example in acetone, chloroform or methanol, and to remove the solvent again, for example by distillation, after thorough mixing.
  • the invention furthermore relates to the process for the preparation of the LC media according to the invention.
  • the LC media according to the invention may also comprise compounds in which, for example, H, N, O, Cl, F have been replaced by the corresponding isotopes like deuterium etc.
  • the following examples explain the present invention without restricting it. However, they show the person skilled in the art preferred mixture concepts with compounds preferably to be employed and the respective concentrations thereof and combinations thereof with one another. In addition, the examples illustrate which properties and property combina- tions are accessible. For the present invention and in the following examples, the structures of the liquid- crystal compounds are indicated by means of acronyms. Unless stated otherwise, the transformation into chemical formulae is done in accordance with Tables A.1 to A.3 below.
  • All radicals C n H 2n+1 , C m H 2m+1 and ClH2l+1 or C n H 2n , C m H 2m and ClH2l are straight-chain alkyl radicals or alkylene radicals, in each case having n, m and l C atoms respectively.
  • n, m and l are independently of each other 1, 2, 3, 4, 5, 6, or 7.
  • Table A.1 shows the codes for the ring elements of the nuclei of the compound
  • Table A.2 lists the bridging units
  • Table A.3 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 B shows illustrative structures of compounds together with their respective abbreviations which are preferred co-compounds according to the claimed mixture concept of the present invention.
  • n, m, k and l are, independently of one another, each an integer, preferably 1 to 9 preferably 1 to 7, k and l may also be 0 and are preferably 0 to 4, more preferably 0 or 2 and most preferably 2, n is preferably 1, 2, 3, 4 or 5 or, in the combination “-nO-”, n is preferably 1, 2, 3 or 4, very preferably 2 or 4, m is preferably 1, 2, 3, 4 or 5 or, in the combination “-Om”, m is preferably 1, 2, 3 or 4, more preferably 2 or 4.
  • the combination “-nVm” preferably is “2V1”.
  • (O)C m H 2m+1 means C m H 2m+1 or OC m H 2m+1 .
  • the LC media according to the invention comprise one or more compounds selected from the group consisting of compounds from Table B.
  • Table C shows possible chiral dopants which can be added to the LC media according to the invention with the concentration from 0 to 5 wt %, preferably 0.01 to 3 wt %. ⁇
  • the LC media preferably comprise 0 to 10% by weight, in particular 0.01 to 5% by weight, particularly preferably 0.1 to 3% by weight, of dopants.
  • the LC media preferably comprise one or more dopants selected from the group consisting of compounds from Table C.
  • Table D Table D shows possible stabilisers which can be added to the LC media according to the invention.
  • n denotes an integer from 1 to 12, preferably 1, 2, 3, 4, 5, 6, 7 or 8, and terminal methyl groups are not shown.
  • the LC media preferably comprise 0 to 10% by weight, in particular 1 ppm to 5% by weight, particularly preferably 1 ppm to 1% by weight, of stabilisers.
  • the LC media preferably comprise one or more stabilisers selected from the group consisting of compounds from Table D. Examples The following examples explain the present invention without restricting it. However, they show the person skilled in the art preferred mixture concepts with compounds preferably to be employed and the respective concentrations thereof and combinations thereof with one another. In addition, the examples illustrate which properties and property combina- tions are accessible.
  • threshold voltage for the present invention relates to the capacitive threshold (V0), also known as the Freedericks threshold, unless explicitly indicated otherwise.
  • the optical threshold may also, as generally usual, be quoted for 10% relative contrast (V10).
  • the process of polymerizing the polymerizable compounds in the PSA displays as described above and below is carried out at a temperature where the LC medium exhibits a liquid crystal phase, preferably a nematic phase, and most preferably is carried out at room temperature.
  • methods of preparing test cells and measuring their electrooptical and other properties are carried out by the methods as described hereinafter or in analogy thereto.
  • the polymerizable compounds are polymerized in the display or test cell by irradiation with UV light of defined intensity for a prespecified time, with a voltage simultaneously being applied to the display (usually 10 V to 30 V alternating current, 1 kHz).
  • tilt angle means the angle between the LC director and the substrate, and "LC director” means in a layer of LC molecules with uniform orientation the preferred orientation direction of the optical main axis of the LC molecules, which corresponds, in case of calamitic, uniaxially positive birefringent LC molecules, to their molecular long axis.
  • the following compounds A-1, A-2, B-1 to B-7, C, D, and/or E of formula I are added to the LC mixtures.
  • Example 1A The nematic LC mixture N1A is formulated as follows. To the mixture N1A are added 100 ppm of the stabiliser H-1-1-1.
  • Example 1B The nematic LC mixture N1B is formulated as follows. To the mixture N1B are added 100 ppm of the stabiliser H-1-1-1.
  • Example 1C The nematic LC mixture N1Cis formulated as follows. To the mixture N1C are added 100 ppm of the stabiliser H-1-1-1.
  • Example 1D The nematic LC mixture N1D is formulated as follows. To the mixture N1D are added 100 ppm of the stabiliser H-1-1-1.
  • Example 1E The nematic LC mixture N1E is formulated as follows.
  • Example 2 The nematic LC mixture N2 is formulated as follows. To the mixture N2 are added 150 ppm of the stabiliser ST-3a-1. Example 3 The nematic LC mixture N3 is formulated as follows.
  • Example 4 The nematic LC mixture N4 is formulated as follows.
  • Example 5 The nematic LC mixture N5 is formulated as follows.
  • Example 6 The nematic LC mixture N6 is formulated as follows. To the mixture N6 are added 50 ppm of the stabiliser ST-9-1.
  • Example 7 The nematic LC mixture N7 is formulated as follows. To the mixture N7 are added 50 ppm of the stabiliser ST-12.
  • Example 8 The nematic LC mixture N8 is formulated as follows. To the mixture N8 are added 100 ppm of the stabiliser H-1-1-1.
  • Example 9 The nematic LC mixture N9 is formulated as follows.
  • Example 10 The nematic LC mixture N10 is formulated as follows.
  • Example 11 The nematic LC mixture N11 is formulated as follows. To the mixture N11 are added 50 ppm of the stabiliser H-2-1-1.
  • Example 13 The nematic LC mixture N13 is formulated as follows.
  • Example 15 The nematic LC mixture N15 is formulated as follows. To the mixture N15 are added 50 ppm of the stabiliser ST-12.
  • Example 16 The nematic LC mixture N16 is formulated as follows.
  • Example 17 The nematic LC mixture N17 is formulated as follows. To the mixture N17 are added 150 ppm of the stabiliser ST-3a-1. Example 18 The nematic LC mixture N18 is formulated as follows.
  • Example 19 The nematic LC mixture N19 is formulated as follows. To the mixture N19 are added 50 ppm of the stabiliser H-2-1-1.
  • Example 20 The nematic LC mixture N20 is formulated as follows. To the mixture N20 are added 100 ppm of the stabiliser ST-8-1.
  • Example 21 The nematic LC mixture N21 is formulated as follows.
  • Example 22 The nematic LC mixture N22 is formulated as follows. To the mixture N22 are added 50 ppm of the stabiliser ST-12. Example 23 The nematic LC mixture N23 is formulated as follows.
  • Example 24 The nematic LC mixture N24 is formulated as follows. To the mixture N24 are added 150 ppm of the stabiliser ST-3a-1. To the mixture N25 are added 150 ppm of the stabiliser ST-3b-1.
  • Example 26 The nematic LC mixture N26 is formulated as follows. To the mixture N26 are added 50 ppm of the stabiliser H-2-1-1.
  • Example 27 The nematic LC mixture N27 is formulated as follows. To the mixture N27 are added 100 ppm of the stabiliser ST-8-1.
  • Example 28 The nematic LC mixture N28 is formulated as follows. To the mixture N28 are added 50 ppm of the stabiliser ST-9-1.
  • Example 29 The nematic LC mixture N29 is formulated as follows. To the mixture N29 are added 50 ppm of the stabiliser ST-12.
  • Example 30 The nematic LC mixture N30 is formulated as follows.
  • Example 31 The nematic LC mixture N31 is formulated as follows. To the mixture N31 are added 150 ppm of the stabiliser ST-3a-1.
  • Example 32 The nematic LC mixture N32 is formulated as follows.
  • Example 33 The nematic LC mixture N33 is formulated as follows. To the mixture N33 are added 50 ppm of the stabiliser H-2-1-1. Example 34 The nematic LC mixture N34 is formulated as follows.
  • Example 35 The nematic LC mixture N35 is formulated as follows. To the mixture N35 are added 50 ppm of the stabiliser ST-9-1.
  • Example 36 The nematic LC mixture N36 is formulated as follows. To the mixture N36 are added 50 ppm of the stabiliser ST-12.
  • Example 37 The nematic LC mixture N37 is formulated as follows.
  • Example 38 The nematic LC mixture N38 is formulated as follows. To the mixture N38 are added 150 ppm of the stabiliser ST-3a-1. Example 39 The nematic LC mixture N39 is formulated as follows.
  • Example 40 The nematic LC mixture N40 is formulated as follows. To the mixture N40 are added 50 ppm of the stabiliser H-2-1-1.
  • Example 41 The nematic LC mixture N41 is formulated as follows.
  • Example 42 The nematic LC mixture N42 is formulated as follows. To the mixture N42 are added 50 ppm of the stabiliser ST-9-1.
  • Example 43 The nematic LC mixture N43 is formulated as follows. To the mixture N43 are added 50 ppm of the stabiliser ST-12.
  • Example 44 The nematic LC mixture N44 is formulated as follows. To the mixture N44 are added 100 ppm of the stabiliser H-1-1-1.
  • Example 45 The nematic LC mixture N45 is formulated as follows. To the mixture N45 are added 150 ppm of the stabiliser ST-3a-1.
  • Example 46 The nematic LC mixture N46 is formulated as follows.
  • Example 47 The nematic LC mixture N47 is formulated as follows. To the mixture N47 are added 50 ppm of the stabiliser H-2-1-1.
  • Example 48 The nematic LC mixture N48 is formulated as follows. wherein CLOY-(c5)1-O2 is To the mixture N48 are added 100 ppm of the stabiliser ST-8-1.
  • Example 49 The nematic LC mixture N49 is formulated as follows.
  • Example 50 The nematic LC mixture N50 is formulated as follows. To the mixture N50 are added 50 ppm of the stabiliser ST-12. Example 51 The nematic LC mixture N51 is formulated as follows.
  • Example 52 The nematic LC mixture N52 is formulated as follows. To the mixture N52 are added 150 ppm of the stabiliser ST-3a-1.
  • Example 53 The nematic LC mixture N53 is formulated as follows. To the mixture N53 are added 150 ppm of the stabiliser ST-3b-1.
  • Example 54 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-171 and 100 ppm of the stabiliser ST-3a-1 to the mixture of Example 1A.
  • Example 55 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-171 and 100 ppm of the stabiliser ST-3a-1 to the mixture of Example 2.
  • Example 56 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-1 and 100 ppm of the stabiliser ST-3b-1 to the mixture of Example 3.
  • Example 57 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-35 and 50 ppm of the stabiliser H-1-1-1 to the mixture of Example 4.
  • Example 58 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-120 and 150 ppm of the stabiliser ST-9-1 to the mixture of Example 5.
  • Example 59 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-142 and 150 ppm of the stabiliser ST-8-1 to the mixture of Example 6.
  • Example 60 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-143 and 150 ppm of the stabiliser ST-3a-1 to the mixture of Example 7.
  • Example 61 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-172 and 50 ppm of the stabiliser H-2-1-1 to the mixture of Example 8.
  • Example 62 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-159 and 50 ppm of the stabiliser H-2-1-1 to the mixture of Example 9.
  • Example 63 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-145 to the mixture of Example 10.
  • Example 64 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-156 and 150 ppm of the stabiliser ST-8-1 to the mixture of Example 11.
  • Example 65 A polymerizable mixture is prepared by adding 0.35% of the polymerizable compound RM-162 and 50 ppm of the stabiliser H-2-1-1 to the mixture of Example 12.
  • Example 66 A polymerizable mixture is prepared by adding 0.4% of the polymerizable compound RM-58 and 150 ppm of the stabiliser ST-3b-1 to the mixture of Example 13.
  • Example 67 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-160 and 150 ppm of the stabiliser ST-8-1 to the mixture of Example 14.
  • Example 68 A polymerizable mixture is prepared by adding 0.4% of the polymerizable compound RM-163 and 100 ppm of the stabiliser ST-9-1 to the mixture of Example 15.
  • Example 69 A polymerizable mixture is prepared by adding 0.4% of the polymerizable compound RM-64 and 150 ppm of the stabiliser ST-3b-1 to the mixture of Example 16.
  • Example 70 A polymerizable mixture is prepared by adding 0.4% of the polymerizable compound a69 and 100 ppm of the stabiliser ST-8-1 to the mixture of Example 17.
  • Example 71 A polymerizable mixture is prepared by adding 0.4% of the polymerizable compound RM-157 and 150 ppm of the stabiliser H-2-1-1 to the mixture of Example 18.
  • Example 72 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-171, 0.1% of the polymerizable compound RM-1 and 150 ppm of the stabiliser ST- 3a-1 to the mixture of Example 19.
  • Example 73 A polymerizable mixture is prepared by adding 0.2% of the polymerizable compound RM-35, 0.2% of the polymerizable compound RM-1 and 100 ppm of the stabiliser ST- 3b-1 to the mixture of Example 20.
  • Example 74 A polymerizable mixture is prepared by adding 0.3% of the polymerizable compound RM-171, 0.1% of the polymerizable compound RM-64 and 100 ppm of the stabiliser H- 2-1-1 to the mixture of Example 21.
  • Example 75 A polymerizable mixture is prepared by adding 0.1% of the polymerizable compound RM-120, 0.3% of the polymerizable compound RM-1 and 150 ppm of the stabiliser H-1- 1-1 to the mixture of Example 22.
  • Example 76 A polymerizable mixture is prepared by adding 0.1% of the polymerizable compound RM-143, 0.3% of the polymerizable compound RM-1 and 150 ppm of the stabiliser ST- 3a-1 to the mixture of Example 23.
  • Example 77 A polymerizable mixture is prepared by adding 0.2% of the polymerizable compound RM-171, 0.2% of the polymerizable compound RM-120 and 150 ppm of the stabiliser ST-8-1 to the mixture of Example 24.
  • Example 78 The nematic LC mixture N78 is formulated as follows. To the mixture N78 are added 100 ppm of the stabiliser H-1-1-1.
  • Example 79 The nematic LC mixture N79 is formulated as follows.
  • Example 80 The nematic LC mixture N80 is formulated as follows. To the mixture N80 are added 150 ppm of the stabiliser ST-3b-1.
  • Example 81 The nematic LC mixture N81 is formulated as follows.
  • Example 82 The nematic LC mixture N82 is formulated as follows. To the mixture N82 are added 100 ppm of the stabiliser ST-8-1.
  • Example 83 The nematic LC mixture N83 is formulated as follows. To the mixture N83 are added 50 ppm of the stabiliser ST-9-1.
  • Example 84 The nematic LC mixture N84 is formulated as follows. To the mixture N84 are added 50 ppm of the stabiliser ST-12.
  • Example 85 The nematic LC mixture N85 is formulated as follows. To the mixture N85 are added 100 ppm of the stabiliser H-1-1-1.
  • Example 86 The nematic LC mixture N86 is formulated as follows.
  • Example 87 The nematic LC mixture N87 is formulated as follows. To the mixture N87 are added 150 ppm of the stabiliser ST-3b-1.
  • Example 88 The nematic LC mixture N88 is formulated as follows. To the mixture N88 are added 50 ppm of the stabiliser H-2-1-1.
  • Example 89 The nematic LC mixture N89 is formulated as follows. To the mixture N89 are added 100 ppm of the stabiliser ST-8-1.
  • Example 90 The nematic LC mixture N90 is formulated as follows. To the mixture N90 are added 50 ppm of the stabiliser ST-9-1.
  • Example 91 The nematic LC mixture N91 is formulated as follows.
  • Example 92 The nematic LC mixture N92 is formulated as follows. To the mixture N92 are added 100 ppm of the stabiliser H-1-1-1. Example 93 The nematic LC mixture N93 is formulated as follows.
  • Example 94 The nematic LC mixture N94 is formulated as follows. To the mixture N94 are added 150 ppm of the stabiliser ST-3b-1. Example 95 The nematic LC mixture N95 is formulated as follows.
  • Example 96 The nematic LC mixture N96 is formulated as follows. To the mixture N96 are added 100 ppm of the stabiliser ST-8-1.
  • Example 97 The nematic LC mixture N97 is formulated as follows.
  • Example 98 The nematic LC mixture N98 is formulated as follows. To the mixture N98 are added 50 ppm of the stabiliser ST-12. Example 99 The nematic LC mixture N99 is formulated as follows.
  • Example 100 The nematic LC mixture N100 is formulated as follows. To the mixture N100 are added 150 ppm of the stabiliser ST-3a-1.
  • Example 101 The nematic LC mixture N101 is formulated as follows. To the mixture N101 are added 150 ppm of the stabiliser ST-3b-1.
  • Example 102 The nematic LC mixture N102 is formulated as follows. To the mixture N102 are added 50 ppm of the stabiliser H-2-1-1.
  • Example 103 The nematic LC mixture N103 is formulated as follows. To the mixture N103 are added 100 ppm of the stabiliser ST-8-1.
  • Example 104 The nematic LC mixture N104 is formulated as follows.
  • Example 105 The nematic LC mixture N105 is formulated as follows. wherein CCP-1V2-1 is To the mixture N105 are added 50 ppm of the stabiliser ST-12.
  • Example 106 The nematic LC mixture N106 is formulated as follows.
  • Example 107 The nematic LC mixture N107 is formulated as follows. wherein PYP-2-1(c3) is To the mixture N107 are added 150 ppm of the stabiliser ST-3a-1.
  • Example 108 The nematic LC mixture N108 is formulated as follows. To the mixture N108 are added 150 ppm of the stabiliser ST-3b-1.
  • Example 109 The nematic LC mixture N109 is formulated as follows. To the mixture N109 are added 50 ppm of the stabiliser H-2-1-1.
  • Example 110 The nematic LC mixture N110 is formulated as follows.
  • Example 111 The nematic LC mixture N111 is formulated as follows. To the mixture N111 are added 50 ppm of the stabiliser ST-9-1.
  • Example 112 The nematic LC mixture N112 is formulated as follows. To the mixture N112 are added 50 ppm of the stabiliser ST-12.
  • Example 113 The nematic LC mixture N113 is formulated as follows. To the mixture N113 are added 100 ppm of the stabiliser H-1-1-1.
  • Example 114 The nematic LC mixture N114 is formulated as follows. To the mixture N114 are added 150 ppm of the stabiliser ST-3a-1.
  • Example 115 The nematic LC mixture N115 is formulated as follows. To the mixture N115 are added 150 ppm of the stabiliser ST-3b-1.

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Abstract

La présente invention concerne un matériau de cristaux liquides (CL) à base d'un mélange de composés polaires, son utilisation à des fins optiques, électro-optiques et électroniques, en particulier dans des affichages CL, en particulier dans des affichages CL du mode de commutation de champ de franges, un affichage CL du mode de commutation de champ de franges comprenant le milieu CL, en particulier un affichage CL à économie d'énergie et un processus de fabrication de l'affichage CL.
PCT/EP2024/056602 2023-03-16 2024-03-13 Milieu à cristaux liquides Pending WO2024189051A1 (fr)

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