WO2025190996A1 - Milieu à cristaux liquides - Google Patents

Milieu à cristaux liquides

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Publication number
WO2025190996A1
WO2025190996A1 PCT/EP2025/056724 EP2025056724W WO2025190996A1 WO 2025190996 A1 WO2025190996 A1 WO 2025190996A1 EP 2025056724 W EP2025056724 W EP 2025056724W WO 2025190996 A1 WO2025190996 A1 WO 2025190996A1
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atoms
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compounds
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another
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Sven Christian Laut
Hee-Kyu Lee
Minghui Yang
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Merck Patent GmbH
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Merck Patent GmbH
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
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    • C09K19/00—Liquid crystal materials
    • 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
    • C09K19/3048—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
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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
    • C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/122—Ph-Ph
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    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/123—Ph-Ph-Ph
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3004—Cy-Cy
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    • C09K19/06—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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    • C09K19/00—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
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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)
    • C09K2019/3019—Cy-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)
    • C09K2019/3025—Cy-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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring

Definitions

  • the present invention relates to liquid-crystalline (LC) media and to energy saving liquid-crystal displays (LCDs) containing these media, especially to high contrast gaming displays and AR/VR headsets.
  • LC liquid-crystalline
  • LCDs energy saving liquid-crystal displays
  • it relates to LC displays of the TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, SA-HB- FFS, SA-XB-FFS, polymer stabilised SA-HB-FFS, polymer stabilised SA-XB-FFS, positive VA or positive PS-VA type.
  • the LC media have positive dielectric anisotropy. LCDs are used in many areas for the display of information.
  • WO 91/10936 discloses a LC display in which the electric signals are generated in such a way that the electric fields have a significant component parallel to the LC layer, and which has since then become known as “in-plane switching” (IPS) display.
  • IPS in-plane switching
  • the principles of operating such a display are described, for example, by R.A. Soref in Journal of Applied Physics, Vol.45, No.12, pp.5466-5468 (1974).
  • IPS displays contain an LC layer between two substrates with planar orientation, where the two electrodes are arranged on only one of the two substrates and preferably have interdigitated, comb-shaped structures. On application of a voltage to the electrodes an electric field with a significant component parallel to the LC layer is generated between them.
  • EP 05885608 discloses various possibilities for the design of the electrodes and for addressing an IPS display.
  • DE 19824137 likewise describes various embodiments of such IPS displays.
  • LC materials for IPS displays of this type are described, for example, in DE 19528104.
  • so-called “fringe-field switching” (FFS) displays have been reported (see, inter alia S.H. Jung et al., Jpn. J. Appl. Phys., Volume 43, No.3, 2004, 1028), which contain two electrodes on the same substrate, one of which is structured in a comb- shaped manner and the other is unstructured.
  • FFS displays have a low viewing-angle depen- dence of the contrast.
  • FFS displays usually contain an LC medium with positive dielectric anisotropy, and an alignment layer, usually of polyimide, which provides planar alignment to the molecules of the LC medium.
  • LCDs of the IPS and FFS electro-optical mode are, in particular, suitable for use in modern desktop monitors, TV sets and multimedia applications.
  • the LC media according to the present invention are preferably used in displays of this type.
  • CMOS complementary metal-oxide-semiconductor
  • CMOS complementary metal-oxide-semiconductor
  • LC media can also advantageously be used in displays having other known addressing means.
  • IPS and FFS technologies are monitors, notebooks, televisions, mobile telephones, tablet PCs, etc. Both the IPS and the FFS technology have certain advantages over other LCD technologies, such as, for example, the vertical alignment (VA) technology, e.g.
  • VA vertical alignment
  • the present invention has the object of providing LC media, in particular for energy saving gaming FFS and IPS displays and AR/VR headsets, but also for TN, positive VA or STN displays, and in particular for active-matrix displays like those addressed by TFTs, which have a high average elastic constant K av in combination with a low response time parameter ⁇ 1 and a low rotational viscosity and a relatively low birefringence ⁇ n. Additionally, they need to have a high specific resistance, low threshold voltage, high dielectric anisotropy, a good low temperature stability (LTS), fast response times, and enable high brightness. In case of FFS displays there is a need for further optimization of response time, contrast, brightness and reliability.
  • LC media as described and claimed hereinafter.
  • Prior art for example WO 2010/099853 A1 and DE 102010027099 A1, discloses thiophene-containing LC media.
  • WO 2010/099853 A1 teaches compounds containing a thiophene-2,5-diyl unit which is linked directly to a 2- and/or 6-substituted 1,4- phenylene unit.
  • WO 2010/099853 A1 describes the development of novel materials for use in LC displays.
  • LC media according to the present invention which contain one or more compounds of the Formula L L in combination with and one or more compounds of Formula S S in which the individual substituents are specified in Claim 1, show several remarkable improvements, especially when being used in FFS mode displays, like a high average elastic constant K av , a low response time parameter ( ⁇ 1 / K 1 ) in combination with a low rotational viscosity as well as a good solubility, and enable fast response times.
  • the LC media according to the present invention have high clearing points, an excellent low temperature stability (LTS) and provide a superior motion picture quality and an improved overall image quality, in particular a high contrast.
  • the present invention relates to a LC medium, characterised in that it comprises one or more compounds of Formula L L and one or more compounds of Formula S S in which the individual substituents, on each occurrence identically or differently, and each, independently of one another, have the following meanings: A 0 , A 1 , A 2 each, independently of one another, denote phenylene-1,4-diyl, in which, in addition, one or two CH groups may be substituted by N and one or more H atoms may be substituted by halogen, CN, CH 3 , CHF 2 , CH 2 F, CF 3 , OCH 3 , OCHF 2 or OCF 3 , cyclohexane-1,4-diyl, in which, in addi- tion, one or two non-adjacent CH 2 groups
  • the LC media according to the present invention are especially suitable for use in energy saving LC displays of the FFS, HB-FFS, XB-FFS and IPS mode for gaming based on dielectrically positive LC media, and polymer stabilised variants thereof.
  • the invention further relates to the use of a LC medium as described above and below for electro-optical purposes, in particular for the use in LC displays, shutter glasses, LC windows, 3D applications, preferably in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-HB-FFS, PS-XB-FFS, SA-HB-FFS, SA-XB-FFS, polymer stabilised SA-HB-FFS, polymer stabilised SA-XB-FFS, positive VA and positive PS-VA displays, very preferably in FFS, HB-FFS, IPS, PS-HB-FFS and PS-IPS displays.
  • the invention further relates to an electro-optical LC display containing a LC medium as described above and below, in particular a TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-HB-FFS, PS-XB-FFS, SA-HB-FFS, SA-XB-FFS, polymer stabilised SA-HB-FFS, polymer stabilised SA-XB-FFS, positive VA or positive PS-VA display, preferably a FFS, HB-FFS, IPS, PS-HB-FFS or PS-IPS display.
  • all atoms may optionally include their isotopes.
  • R 1 , R 2 , R 3 and R 4 preferably denote straight-chain alkyl having 1 to 6 C atoms or an alkenyl group having 2 to 6 C atoms.
  • R 1 , R 2 , R 3 or R 4 denotes an alkoxy or oxaalkyl group it may also contain one or more additional oxygen atoms, provided that oxygen atoms are not linked directly to one another.
  • R 1 , R 2 , R 3 or R 4 are selected from or C 2-12 -alkenylene S2 is H, C 1-12 -alkyl or C 2-12 -alkenyl, and very preferably one , -OCH 2 OCH 3 , -O(CH 2 ) 2 OCH 3 , -O(CH 2 ) 3 OCH 3 , -O(CH 2 ) 4 OCH 3 , -O(CH 2 ) 2 F, -O(CH 2 ) 3 F, -O(CH 2 ) 4 F.
  • R 1 , R 2 , R 3 or R 4 denotes an alkenyl group, this may be straight-chain or branched.
  • It is preferably straight-chain and has 2 to 10 C atoms. Accordingly, it denotes, in particu- lar, vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl, oct-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, non-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl, dec-1- , -2- , -3- , -4- , -5- , -6- , -7- , -8-enyl, dec-1- , -2
  • R 1 , R 2 , R 3 or R 4 denotes an alkyl or alkenyl group which is at least monosubstituted by halogen, this group is preferably straight-chain, and halogen is preferably F or Cl. In the case of polysubstitution, halogen is preferably F.
  • the resultant groups also include perfluorinated groups. In the case of monosubstitution, the fluorine or chlorine substituent may be in any desired position, but is preferably in the ⁇ -position.
  • R 1 , R 2 , R 3 or R 4 denotes alkyl, alkenyl, alkynyl or alkoxy having up to 12, preferably up to 8 C atoms, each of which is optionally substituted by halogen, in particular by F, particularly preferred are H, F, alkyl, alkenyl or alkynyl having up to 8 C atoms.
  • Preferred alkyl groups are, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl.
  • Preferred alkenyl groups are, for example, ethenyl, propenyl, butenyl and pentenyl.
  • Preferred alkynyl groups are, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl and octynyl.
  • Preferred alkoxy groups are, for example, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy.
  • Halogen preferably denotes F or Cl, F being mostly preferred.
  • R 1 and R 2 each, independently of one another, denote an alkyl or an alkoxy group having 1 to 6 C atoms or an alkenyl or an alkenyloxy group having 2 to 6 C atoms in which one or more CH 2 groups are optionally substituted in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be substituted by a halogen atom; and Y 1 H or CH 3 .
  • Particularly preferred compounds of Formula L-2 and 3 are those selected from the group consisting of the following subformulae:
  • Particularly preferred compounds of Formula L-1 may be selected from one of the following: Very preferred are the compounds of formulae L-2-1, L-2-2, L-2-3 and L-2-4, mostly preferred is the compound formula L-2-2.
  • the proportion of the compounds of Formula L or its subformulae in the LC medium is preferably from 2 to 35%, very preferably from 3 to 30%, most preferably from 4 to 20% by weight.
  • the LC medium contains 1, 2 or 3 compounds of Formula L or its subformulae.
  • LC media comprising the compounds of Formula S in denotes phenylene-1,4-diyl, in which, in addition, one or two CH groups may be substituted by N and one or more H atoms may be substituted by halogen, CN, CH 3 , CHF 2 , CH 2 F, OCH 3 , OCHF 2 , CF 3 or OCF 3 .
  • Particularly preferred are compounds in more ; and very particularly preferably in which A 0 .
  • the preferred compounds of the Formula S result in LC media having a particularly high clearing point, low rotational viscosity, a broad nematic phase range, high birefringence and an excellent thermal and UV stability.
  • a 0 , A 1 and A 2 in Formula S particularly preferably denote phenylene-1,4-diyl, which may also be mono- or polysubstituted by F, furthermore cyclohexane-1,4-diyl, cyclo- hexenylene-1,4-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl.
  • Z 1 and Z 2 in Formula S particularly preferably denote -CF 2 O-, -OCF 2 - or a single bond, wherein a single bond is particularly preferred.
  • R 3 and R 4 each, independently of one another, denote H, F, Cl, Br, -CN, -SCN, -NCS, SF 5 , halogen, or alkyl, alkenyl or alkynyl having up to 8, preferably up to 5 C atoms, each of which is optionally substituted by halogen, in particular by F.
  • R 3 and R 4 in Formula S denote H, halogen, or alkyl, alkenyl, alkynyl or alkoxy having up to 12, preferably up to 8 C atoms, each of which is optionally substituted by halogen, in particular by F, particularly preferred are H, F, alkyl, alkenyl or alkynyl having up to 8 C atoms.
  • at least one group is not H, particularly preferably both groups R 3 and R 4 are not H.
  • R 3 is very particularly preferably equal to alkyl.
  • R 4 is furthermore preferably H, alkyl, alkyl which is substituted by at least one fluorine or fluorine.
  • R 3 is alkyl and R 4 is H or alkyl.
  • R 3 , R 4 each, independently of one another, very particularly preferably denote unbranched alkyl having 1 to 5 C atoms. If R 3 and R 4 denote substituted alkyl, alkoxy, alkenyl or alkynyl, the total number of C atoms in the two groups R 3 and R 4 is preferably less than 10.
  • Preferred alkyl groups are, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl.
  • Preferred alkenyl groups are, for example, ethenyl, propenyl, butenyl and pentenyl.
  • Preferred alkynyl groups are, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl and octynyl.
  • Preferred alkoxy groups are, for example, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy.
  • Halogen preferably denotes F or Cl, F being mostly preferred.
  • Particularly preferred compounds of the Formula S are those selected from the following sub-formulae: 1 2 3 4 1 5 6 in which Y 2 , Y 3 , R 3 and R 4 and L 3 to L 8 have the meanings indicated in general Formula S.
  • R 3 and R 4 may denote optionally fluorinated alkyl or alkoxy having 1 to 12 C atoms, optionally fluorinated alkenyl or alkynyl having 2 to 12 C atoms, optionally fluorinated cycloalkyl having 3 to 12 C atoms.
  • Y 2 and Y 3 are preferably a H atom or a methyl group. Particularly preferred are optionally fluorinated alkyl, alkenyl or alkynyl having up to 5 C atoms.
  • L 3 in the Formulae S-1-1 to S-1-6 preferably denotes F. In the Formulae S-1-4 to S-1-6, L 5 to L 8 preferably denote H.
  • the compounds of Formula S are selected from the following structures: 1 where R 3 has the same meaning as in the general Formula S; denotes a straight-chain or branched alkyl or alkoxy group having 1 to 6 C atoms, or an akenyl, alkenyloxy, alkoxyalkyl group having 2 to 6 C atoms, or a cycloalkyl or a cycloalkoxy group having 3 to 12 C atoms, in which one or more non-adjacent CH 2 groups are optionally substituted in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be substituted by a halogen atom; alternatively, is X 0 , wherein X 0 a F atom or an alkyl or an alkoxy group having 1 to 3 C atoms or an alkenyl or an alkenyloxy group having 2 or 3 C atoms in which one or more H atoms are replaced by
  • LC media according to the present invention having a particularly advantageous properties are obtainable with the following compounds of the general Formula S: 1 2 3 wherein Y 2 , Y 3 , R 3 and R 4 are as defined above.
  • the LC medium comprises one or more compound of Formula S-2-4 and/or one or more compound of Formula S-2-7.
  • LC media comprise the following compounds of Formula S: 1 2 3 4 5 6 7 8 9 wherein n and m each, independently of one another, denote 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.
  • Especially preferred compounds of Formula S include, in particular, one or more of the following: 1 1 2 3 4 5 6 7 8 9 As a further possibility, the following compounds of Formula S can be used: 1 2 3 4 5 6 7 8 9 As a further possibility, the following compounds of Formula S can be used: 1 2 3 4 5 6 7 5 1 2 3 4 5 Very preferred are the compounds of formulae S-3-9-2 and S-3-5-1.
  • the proportion of the compounds of Formula S or its subformulae in the LC medium is preferably from 1 to 40%, very preferably from 2 to 30%, most preferably from 3 to 20% by weight.
  • the LC medium contains 1, 2 or 3 compounds of Formula S or its subformulae.
  • the LC medium may additionally comprise one or more compounds selected from the following Formulae II and III: II III wherein the individual substituents, independently of each other and on each occurrence identically or differently, have the following meanings: R 0 has one of the meanings given for R 1 and R 2 in Formula L, X 0 independently of one another F, Cl, an alkyl group, an alkenyl group, an alkoxy group or an alkenyloxy group having up to 6 C atoms, in which one or more H atoms has been substituted by a halogen atom, L 1-8 independently of one another H, F or Cl, and has one of the meanings given Y 1 in Formula L.
  • R 0 has one of the meanings given for R 1 and R 2 in Formula L
  • X 0 independently of one another F, Cl
  • an alkyl group an alkenyl group, an alkoxy group or an alkenyloxy group having up to 6 C atoms, in which one or more H atoms has been substituted by a
  • the LC medium comprises one or more compounds of the Formula II selected from the following subformulae: 1 2 3 4 5 6 7 in have the meanings given in the Formula II.
  • R 0 preferably denotes alkyl having 1 to 6 C atoms or cycloalkyl having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl
  • the LC medium contains one or more compounds of the Formula II or their subformulae as described above and below, wherein Y 0 is CH 3 .
  • R 0 preferably denotes alkyl having 1 to 6 C atoms or cycloalkyl having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl
  • the proportion of the compounds of the Formula II in the LC medium is typically from 0 to 30%, very preferably from 1 to 20%, most preferably from 2 to 15% by weight.
  • the LC medium comprises one or more compounds of the Formula III selected from the following subformulae: 1 2 3 4 5 6 7 8 in have the meanings given in the Formula II.
  • Particularly preferred compounds are those of the Formulae III-1, III-4, III-6, III-16, III- 19, III-20 and III-22.
  • R 0 preferably denotes alkyl having 1 to 6 C atoms or cycloalkyl having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl
  • the LC medium may contain one or more compounds of the Formula III or their subformulae as described above and below Y 0 is CH 3 .
  • the LC medium according to this preferred embodiment comprises one or more compounds of the Formula III selected from the following subformulae: 1 2 3 4 5 6 7 3 in have the meanings given in the Formula III.
  • Preferred compounds are those of the Formula IIIA-1, IIIA-4, IIIA-6, IIIA-16, IIIA-19 and IIIA-20.
  • R 0 preferably denotes alkyl having 1 to 6 C atoms or cycloalkyl having 3 to 6 C atoms, very preferably ethyl, propyl, butyl or pentyl
  • the proportion of the compounds of the Formula III in the LC medium is preferably from 2 to 60%, very preferably from 5 to 50%, most preferably from 10 to 30% by weight.
  • the compounds of the Formula IV are preferably selected from the following formulae: a in have the meanings indicated in the Formulae II and III.
  • the compounds of the Formula IVa are preferably represented by the following subformulae: 1 1
  • the compounds of the Formula IVb are preferably represented by the following formulae: 1 2
  • the compounds of the Formulae IVc are preferably represented by the following subformulae: in which R 0 has the meanings indicated in the Formula II and is preferably alkyl having 1 to 6 C atoms or cycloalkyl having 3 to 6 C atoms, very preferably ethyl, n-propyl, n- butyl or n-pentyl.
  • the compound(s) of the Formula IVc, in particular of the Formula IVc-1, is (are) preferably employed in the LC media according to the invention in amounts of from 1% to 20% by weight, particularly preferably from 2 to 15% by weight.
  • the compounds of the Formula V are preferably selected from the following subformulae: in have the meanings indicated in the Formula II.
  • the compounds of the Formula VI are preferably selected from the following subformulae: e in have the meanings indicated in the Formula II.
  • Preferred compounds of the Formulae VIa to VIe are those selected from the following subformulae: 1 2 3 1 "alkyl" being an alkyl group with 1 to 6 C atoms, being preferably selected from ethyl, propyl, butyl, pentyl, wherein propyl is particularly preferred.
  • the compounds of the Formula VII are preferably selected from the following subformulae: in have the meanings indicated in the Formula II.
  • the LC medium according to this first preferred embodiment may contain one or more compounds of the Formulae L and S, one or more compounds selected from the Formulae Z1, Z2 and Z3, and one or more compounds selected from the Formulae Y and B.
  • the LC media according to this first preferred embodiment are especially suitable for use in LC displays of the HB-FFS or PS-HB-FFS mode.
  • R 1 and R 2 preferably denote straight-chain alkyl or alkoxy having 1 to 6 C atoms, furthermore alkenyl having 2 to 6 C atoms, in particular vinyl, 1E-propenyl, 1E-butenyl, 3-butenyl, 1E-pentenyl, 3E-pentenyl or 4-pentenyl.
  • substituents L 1 and L 2 denote F.
  • one of the substituents L 1 and L 2 denotes F and the other denotes Cl.
  • the LC medium contains one or more compounds of the Formula Y selected from the following subformulae: wherein R 1 , R 2 , Z x and Z y have the meanings given in the Formula Y, a denotes 1 or 2, b denotes 0 or 1, L 1 , L 2 denote F or Cl, preferably F, and L 5 denotes a H atom or CH 3 , 4
  • a denotes 1 or 2 b denotes 0 or 1
  • L 1 , L 2 denote F or Cl, preferably F
  • L 5 denotes a H atom or CH 3 , 4
  • both L 1 and L 2 denote F or one of L 1 and L 2 denotes F and the other denotes Cl
  • both L 1 and L 2 denote F or one of L 1 and L 2 denotes F and the other denotes Cl.
  • the LC medium comprises one or more compounds of the Formula Y1 selected from the group consisting of the following subformulae: 1 2 3 4 in which a denotes 1 or 2, “alkyl” and “alkyl*” each, independently of one another, denote a straight-chain alkyl group having 1 to 6 C atoms, “alkenyl” denotes a straight-chain alkenyl group having 2 to 6 C atoms, and denotes a H atom or CH 3 .
  • the LC medium contains one or more compounds of the Formula Y1 selected from the Formulae Y1-1, Y1-2, Y1-7, Y1-12, Y1-17, Y1-22, Y1-40, Y1-41, Y1- 42, Y1-44, Y1-50 and Y1-68.
  • L 5 preferably denotes a H atom.
  • the LC medium comprises one or more compounds of the Formula Y2 selected from the group consisting of the following subformulae: 1 2 3 4 5 6 in which “alkyl” and “alkyl*” each, independently of one another, denote a straight-chain alkyl group having 1 to 6 C atoms, and “alkenyl” denotes a straight-chain alkenyl group having 2 to 6 C atoms, (O) denotes an oxygen atom or a single bond, and L 5 denotes a H atom or CH 3 , preferably a H atom.
  • the LC medium contains one or more compounds of the Formula Y2 selected from Formulae Y2-2 and Y2-10.
  • the proportion of the compounds of the Formula Y1 or its subformulae in the LC medium is preferably from 0 to 10% by weight.
  • the proportion of the compounds of the Formula Y2 or its subformulae in the LC medium is preferably from 0 to 10% by weight.
  • the total proportion of the compounds of the Formula Y1 and Y2 or their subformulae in the medium is preferably from 1 to 20%, very preferably from 2 to 15% by weight.
  • the LC medium contains 1, 2 or 3 compounds of the Formula Y1 and Y2 or their subformulae, very preferably selected from the Formulae Y1-2, Y1-22, Y1-66, Y1- 70, Y2-6 and Y2-22.
  • the LC medium contains one or more compounds of the Formula Y of the following subformula: Y3 wherein L 1 , L 2 , L 5 , R 1 and R 2 have one of the meanings given in the Formula L for L 1 , respectively.
  • Preferred compounds of the Formula Y3 are selected from the group consisting of the following subformulae: 1 2 3 4 5 6 7 8 in which, “alkyl” and “alkyl*” each, independently of one another, denote a straight-chain alkyl group having 1 to 6 C atoms; “alkenyl” and “alkenyl*” each, independently of one another, denote a straight-chain alkenyl group having 2 to 6 C atoms; and (O) denotes an oxygen atom or a single bond.
  • Particularly preferred compounds of the Formula Y3 are selected from the group consisting of following subformulae: wherein “alkoxy” and “alkoxy*” each, independently of one another, preferably denote straight-chain alkoxy with 3, 4, or 5 C atoms.
  • both L 1 and L 2 denote F.
  • one of the substituents L 1 and L 2 denotes F and the other denotes Cl.
  • the proportion of the compounds of the Formula Y3 or its subformulae in the LC medium is preferably from 0 to 10%, very preferably from 1 to 6% by weight.
  • the LC medium contains 1, 2 or 3 compounds of the Formula Y3 or its subformulae, more preferably of the Formula Y3-6, very preferably of the Formula Y3- 6A.
  • the LC medium contains one or more compounds of the Formula Y of the subformula Y4: in which R 1 and R 2 each, independently of one another, have one of the meanings indicated above in the Formula Y, and each, independently of one another, denote in which L 5 denotes F or Cl, preferably F, and L 6 denotes F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 , preferably F, and preferably at least one of the rings G, I and K is different from unsubstituted benzene.
  • Especially preferred compounds of the Formula Y4 are selected from the group consisting of the following subformulae: 1 in which R denotes a straight-chain alkyl or alkoxy group having 1 to 6 C atoms, (O) denotes an oxygen atom or a single bond, and m denotes an integer from 1 to 6.
  • R preferably denotes methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy or pentoxy.
  • the proportion of the compounds of the Formula Y4 or its subformulae in the medium is preferably from 0 to 10%, very preferably from 1 to 6% by weight.
  • the LC medium comprises one or more compounds of the Formula Y of the following subformula wherein R 1 , R 2 , L 1 , L 2 , X, x and Z x have the meanings given in the Formula Y, and wherein at least one of the rings X is cyclohexenylene.
  • R 1 , R 2 , L 1 , L 2 , X, x and Z x have the meanings given in the Formula Y, and wherein at least one of the rings X is cyclohexenylene.
  • both substituents L 1 and L 2 denote F.
  • one of the substituents L 1 and L 2 denotes F and the other denotes Cl.
  • the compounds of the Formula LY are preferably selected from the group consisting of the following subformulae: 1 in which R 1 has the meaning indicated in the Formula Y above, (O) denotes an oxygen atom or a single bond, and v denotes an integer from 1 to 6.
  • the medium contains 1, 2 or 3 compounds of the Formula LY, very preferably of the Formula LY4.
  • the proportion of the compounds of the Formula LY or its subformulae in the medium is preferably from 1 to 10% by weight.
  • the medium comprises one or more compounds of the Formula Y represented by the following subformula: wherein R 1 , R 2 , L 1 , L 2 , Y, y and Z y have the meanings given in the Formula Y, and wherein at least one of the rings Y is tetrahydropyrane.
  • the compounds of the Formula AY are preferably selected from the group consisting of the following subformulae: 2 3 0 in which R 1 has the meaning indicated above, “alkyl” denotes a straight-chain alkyl group having 1 to 6 C atoms, (O) denotes an oxygen atom or a single bond, and v denotes an integer from 1 to 6.
  • V-formula T-1a offers advantages over the use of T-1b in terms of low temperature stability of the resulting LC medium.
  • Very preferred compounds of Formula T are those selected from the group consisting of the following subformulae: 1 2 3 4 5 6 7 8 9 11 1 2 3 4 5 5 2 1 2 3 4 5 6 preferably H.
  • LC media comprising compounds of the following sub-formulae ST-1, ST-2 and ST-3 showed a particularly high long-term thermal and UV stability: 1 2 3 4 in which the individual substituents have the following meanings: ; R 21 and R 22 each, independently of one another, denote a H atom or an alkyl or alkoxy group having 1 to 7 C atoms, and r denotes 0 or 1.
  • the compounds of the general Formula ST can be selected from the following specific structures: 1 2 3 4 5 6 7 8 1 2 3 4 5 6 7
  • the LC medium according to the present invention may comprise at least one further sterically hindered phenol, which is mentioned in Table B below.
  • the group denotes a group selected from the group of the formulae , .
  • p is 2, which may be identical to or different from those described above
  • in the compounds of the Formula H denotes a group selected from the group of the formulae H , H .
  • the group on each occurrence, independently of one another, denotes , , .
  • the LC media comprise in each case one or more compounds of the Formula H selected from the following group of the compounds of the formulae: 1 2 3 4 5 6 7 8 9 and 21
  • Preferred content of the one or more compounds of Formula H in the LC medium depends inter alia on the inherent chemical stability of the LC medium as well as on the nature of the compound of Formula H.
  • Compounds of Formula H in which R 16 denotes O•, which are known as NO radical type HALS are preferably used in proportion ranging from 50 ppm to 1000 ppm, based on the weight of the LC medium.
  • LC media are selected from the following preferred embodiments, including any combination thereof: ⁇ a compound of the Formulae L and S in combination with a compound of the Formula LP1, Z1 to Z11 and III ⁇ a compound of the Formulae L and S in combination with a compound of the Formula LP2, Z1 to Z11 and III ⁇ a compound of the Formulae L and S in combination with a compound of the Formula LP1, LP2, III and a compound of the Formula Z1 and Z4 -
  • the LC medium comprises one or more compounds of the Formulae L and S or its subformulae and LP1 and/or LP2, III and one or more compounds selected from the group consisting of the Formulae Z1, Z2, Z3, Z4, Z5, V, VI, VII, VIII, XIV, X
  • the LC medium comprises one or more compounds of the Formulae L and S or its subformulae and LP1 and/or LP2, III and one or more compounds selected from the group consisting of the Formulae Z1, Z2, Z3, Z4, Z5, IV, VI, XII, XIV, XVI, XVIIa, XVIIb, XVIIc, XX, LP1-1, XXIII, XXIX and their subformulae.
  • the LC medium comprises one or more compounds selected from the group consisting of the Formula III-1, III-4, III-6, III-16, III-19 and III-20, very preferably from the group consisting of the Formula III-1, III-6, III-16 and III-20.
  • the individual concentration of each of these compounds is preferably from 2 to 15% by weight.
  • the total concentration of these compounds is preferably from 5 to 30% by weight.
  • the LC medium comprises one or more compounds of the Formula IV, preferably selected from the Formula IVa or IVc, very preferably from the Formula IVa-1 or IVc- 1, most preferably of the Formula IVc-1.
  • the individual concentration of each of these compounds is preferably from 2 to 15% by weight.
  • the total concentration of these compounds is preferably from 5 to 20% by weight.
  • the LC medium comprises one or more compounds of the Formula VI, preferably selected from the Formula VIb.
  • the individual concentration of each of these compounds is preferably from 1 to 20% by weight.
  • the total concentration of these compounds is preferably from 5 to 20% by weight.
  • the LC medium comprises one or more compounds of the Formula Z1, preferably selected from the Formula Z1-1.
  • the total concentration of these compounds is preferably from 10 to 70 % by weight, more preferably 20 to 60 % by weight, even more preferably 30 to 50 % by weight.
  • the LC medium comprises one or more compounds of the Formula Z2, preferably selected from the Formulae Z2-1 and Z2-2.
  • the total concentration of these compounds is preferably from 2 to 35%, very preferably from 3 to 25% by weight.
  • the LC medium comprises from 5 to 20% by weight of compounds of the Formula Z3, preferably of the Formula Z3-1.
  • the LC medium comprises from 5 to 20% by weight of compounds of the Formula Z4, preferably of the Formula Z4-1.
  • the LC medium comprises from 1 to 30%, very preferably from 2 to 15% by weight of compounds of Formula Z5.
  • the LC medium comprises one or more compounds of the Formula LP1-1, preferably of the Formula LP1-1a or LP2-1b, very preferably of the Formula LP1-1a. The concentration of these compounds is preferably from 1 to 15% by weight.
  • the LC medium comprises from 1 to 15% by weight of compounds of the Formula LP2-1b.
  • the LC medium comprises one or more compounds of the Formula XII, preferably of the Formula XIIa or XIIb, very preferably of the Formula XIIa, most preferably of the Formula XIIa-1.
  • the concentration of these compounds is preferably from 2 to 15% by weight.
  • the LC medium comprises from 1 to 15% by weight of compounds of the Formula XIIb.
  • the LC medium comprises one or more compounds of the Formula XIV, preferably of the Formula XIVd, very preferably of the Formula XIVd-1. The concentration of these compounds is preferably from 2 to 10% by weight.
  • the LC medium comprises one or more compounds of the Formula XVIb, preferably of the Formula XVIb-1, XVIb-2 and/or XVIb-3. The concentration of these compounds is preferably from 2 to 15% by weight.
  • the LC medium comprises one or more compounds of the Formula XVIc, preferably of the Formula XVIc-1, XVIc-2 and/or XVIc-3.
  • the concentration of these compounds is preferably from 2 to 20% by weight.
  • the LC medium comprises one or more compounds selected from the group consisting of the Formulae XVIIa, XVIIb and XVIIc, very preferably of the Formula XVIIa wherein L is H and of the Formula XVIIb wherein L is F.
  • the total concentration of these compounds is preferably from 0.5 to 5% by weight.
  • the LC medium comprises one or more compounds of the Formula XX, preferably of the Formula XXa.
  • the concentration of these compounds is preferably from 2 to 10% by weight.
  • the LC medium comprises one or more compounds of the Formula XXI, preferably of the Formula XXIa.
  • the concentration of these compounds is preferably from 2 to 10% by weight.
  • the LC medium comprises one or more compounds of the Formula XXIII, preferably of the Formula XXIIIa. The concentration of these compounds is preferably from 0.5 to 5% by weight.
  • the LC medium comprises one or more compounds of the Formula XXIX, preferably of the Formula XXIXa. The concentration of these compounds is preferably from 2 to 10% by weight.
  • the LC medium comprises one or more compounds of the Formula XXX. The concentration of these compounds is preferably from 2 to 10% by weight.
  • the LC medium comprises one or more compounds of the Formula XII. The concentration of these compounds is preferably from 2 to 10% by weight.
  • the LC medium comprises one or more compounds of the Formulae L and S, preferably of the Formulae L-2 and S-1-4-1, and LP1 and/or LP2, III, one or more compounds selected from the group consisting of the Formulae Z1, Z2 and Z4 or their subformulae, one or more compounds selected from the group consisting of the Formula XIV, one or more compounds selected from the group consisting of the Formulae IV, VI, XX, XXIII and XXIX or their subformulae, and one or more compounds selected from the group consisting of the Formulae LP2-1, XVI, XVIIa, XVIIb, XVIIc or their subformulae.
  • the LC medium comprises one or more compounds of Formulae L and S, preferably of the Formulae L-2 and S-2-4, S-2-7, LP1 and/or LP2, III, one or more compounds selected from the group consisting of the Formulae Z1, Z2, Z3, Z4 and Z5 or their subformulae, one or more compounds selected from the group consisting of the Formula XIVd or their subformulae, one or more compounds selected from the group consisting of the Formulae IVc, VIb, XXa, XXIIIa and XXIXa or their subformulae, and one or more compounds selected from the group consisting of the Formulae LP1-1b, XVIb, XVIc, XVIIa, XVIIb, XVIIc or their subformulae.
  • the LC medium comprises one or more compounds of the Formulae L and S, preferably of the Formulae L-2 and S-1-4-1, LP1 and/or LP2, III, one or more compounds selected from the group consisting of the Formulae Z1, Z2 and Z3 or their subformulae, one or more compounds of the Formula Y, preferably selected from the group consisting of the Formulae Y1 and Y2, one or more compounds selected from the group consisting of the Formula XIV, one or more compounds selected from the group consisting of the Formulae III, IV, VI, XX, XIII and XXIX or their subformulae, and one or more compounds selected from the group consisting of the Formulae LP2- 1, XVI, XVIIa, XVIIb, XVIIc or their subformulae.
  • the LC medium comprises one or more compounds of the Formulae L and S, preferably of the Formulae L-2 and S-2-4, S-2-7, LP1 and/or LP2, one or more compounds selected from the group consisting of the Formulae Z1, Z2, Z3, Z4 and Z5 or their subformulae, one or more compounds of Formula B, preferably selected from the group consisting of the Formulae B1, B2 and B3, one or more compounds of the Formula XIVd or their subformulae, one or more compounds selected from the group consisting of the Formulae III, IVc, VIb, XXa, XXIIIa and XXIXa or their subformulae, and one or more compounds selected from the group consisting of the Formulae LP1-1b, XVIb, XVIc, XVIIa, XVIIb, XVIIc or their subformulae.
  • the LC medium comprises further compounds selected from the group of the compounds of the Formula Z1, Z2, Z3, IV, LP1-1, XIV, XVI, XVIIa, XVIIb, XVIIc, XXI, XXIII, XXIX, XXX and XXIV or their subformulae.
  • the LC medium comprises further compounds selected from the group of the compounds of the Formulae Z1, Z2, Z3, IV, LP2-1, XIV, XVI, XVIIa, XVIIb, XVIIc, XXI, XXIII, XXIX, XXX and XXIV or their subformulae.
  • the proportion of compounds of the Formulae L and S or its subformulae in the LC medium is from 1 to 30%, very preferably from 2 to 25%, most preferably from 2 to 20% by weight.
  • the proportion of compounds of the Formulae Z1, Z2, Z3, Z4 and Z5 or their subformulae in the LC medium as a whole is from 10 to 65%, very preferably from 20 to 60% by weight.
  • the proportion of compounds of the Formula Y or its subformulae in the LC medium as a whole is from 0 to 15%, very preferably from 2 to 10% by weight.
  • the proportion of compounds of the Formula B or its subformulae in the LC medium as a whole is from 0 to 15%, very preferably from 2 to 10% by weight.
  • the proportion of compounds of the Formulae III, IV-VIII, XVIII-XXIII and XXVII-XXX in the LC medium as a whole is 30 to 60% by weight.
  • alkyl or "alkyl*" in this application encompasses straight-chain and branched alkyl groups having 1 to 6 carbon atoms, in particular the straight-chain groups methyl, ethyl, propyl, butyl, pentyl and hexyl. Groups having 2 to 5 carbon atoms are generally preferred.
  • alkenyl groups are vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl and 5-hexenyl.
  • fluoroalkyl preferably encompasses straight-chain groups having a terminal fluorine, i.e.
  • oxaalkyl or "alkoxy” preferably encompasses straight-chain groups of the Formula C n H 2n+1 -O-(CH 2 ) m , in which n and m each, independently of one another, denote 1 to 6. m may also denote 0.
  • the alkoxy or oxaalkyl group can also contain one or more further O atoms such that oxygen atoms are not directly linked to one another.
  • 1E-alkenyl groups, 3E-alkenyl groups, 2E-alkenyloxy groups and the like generally result in shorter addressing times, improved nematic tendencies and a higher ratio between the elastic constants K 3 (bend) (splay) compared with alkyl and alkoxy groups.
  • 4-Alkenyl groups, 3-alkenyl groups and the like generally give lower threshold voltages and lower compared with alkyl and alkoxy groups.
  • the LC media according to the invention are distinguished, in particular, by high ⁇ values and thus have significantly faster response times than the LC media from the prior art.
  • the optimum mixing ratio of the compounds of the above-mentioned formulae depends substantially on the desired properties, on the choice of the components of the above- mentioned formulae and on the choice of any further components that may be present. Suitable mixing ratios within the range indicated above can easily be determined from case to case.
  • the total amount of compounds of the above-mentioned formulae in the LC media according to the invention is not crucial.
  • the LC media can therefore comprise one or more further components for the purposes of optimisation of various properties. However, the observed effect on the desired improvement in the properties of the medium is generally greater, the higher the total concentration of compounds of the above-mentioned formulae.
  • a favourable synergistic action with the compounds of the Formulae L and S results in particularly advantageous properties.
  • LC media comprising compounds of the Formulae L and S, III are distinguished by their low threshold voltage.
  • the individual compounds of the above-mentioned formulae and the subformulae thereof which can be used in the LC media according to the invention are either known or can be prepared analogously to the known compounds.
  • VHR voltage holding ratio
  • the proportion of antioxidants and light stabilisers, like those of the Formula ST and H, as described above or listed in Table G, in the LC medium is from 10 to 2000 ppm, very preferably from 30 to 1000 ppm.
  • 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, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (cf., for example, Haller et al., Mol. Cryst. Liq.
  • the acronyms are composed of the codes for the ring elements with optional linking groups, followed by a first hyphen and the codes for the left-hand end group, and a second hyphen and the codes for the right-hand end group.
  • Table D shows illustrative structures of compounds together with their respective abbreviations. in which n and m are each integers, and the three dots "" are placeholders for other abbreviations from this table.
  • Table H shows illustrative reactive mesogenic compounds (RMs) which can be used in the LC media in accordance with the present invention.
  • RMs reactive mesogenic compounds
  • the LC media according to the invention may optionally comprise one or more polymerizable compounds, preferably selected from the polymerizable compounds of the Formulae RM-1 to RM-184.
  • compounds RM-1, RM-4, RM-8, RM-17, RM- 19, RM-35, RM-37, RM-39, RM-40, RM-41, RM-48, RM-52, RM-54, RM-57, RM-58, RM-64, RM-74, RM-76, RM-88, RM-91, RM-102, RM-103, RM-109, RM-116, RM-117, RM-120, RM-121, RM-122, RM-139, RM-140, RM-142, RM-143, RM-145, RM-146, RM-147, RM-149, RM-156 to RM-163, RM-169, RM-170 and RM-171 to RM-184 are particularly preferred.
  • Table I shows self-alignment additives for vertical alignment which can be used in LC media for SA-FFS, SA-HB-FFS and SA-XB-FFS displays according to the present invention:
  • the LC media, SA-VA and SA-FFS displays according to the present invention comprise one or more SA additives selected from the Formulae SA-1 to SA-49, preferably from the Formulae SA-14 to SA-49, very preferably from the Formulae SA-20 to SA-34 and SA-44, in combination with one or more RMs.
  • SA additives selected from the Formulae SA-1 to SA-49, preferably from the Formulae SA-14 to SA-49, very preferably from the Formulae SA-20 to SA-34 and SA-44, in combination with one or more RMs.
  • C crystalline state
  • N nematic phase
  • S smectic phase
  • I isotropic phase.
  • the data between these symbols represent the transition temperatures.
  • Example M1 A nematic LC medium is formulated as follows: Mixture Example S1 (stabilised with compound of Formula H-3-1) A nematic LC mixture according to the invention is formulated as follows: Compound of 1000 ppm Formula H-3-1 Addition of 1000 ppm of the compound of Formula H-3-1 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M1, without affecting the remaining physical properties of the mixture M1. 1
  • Example M2 A nematic LC medium is formulated as follows: .
  • Example S2 (stabilised with compound of Formula ST-2-3)
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 500 ppm of the compound of the Formula ST-2-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M2, without affecting the remaining physical properties of the mixture M2. 3
  • Example M3 A nematic LC medium is formulated as follows:
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 500 ppm of the compound of the Formula ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M3, without affecting the remaining physical properties of the mixture M3.
  • Example M4 A nematic LC medium is formulated as follows: Mixture Example S4 (stabilised with compound of Formula H-3-5) A nematic LC mixture according to the invention is formulated as follows: Mixture M4 99.995 wt.-% Compound of 50 ppm Formula H-3-5 Addition of 50 ppm of the compound of the Formula H-3-5 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M4, without affecting the remaining physical properties of the mixture M4. 5
  • Example M5 A nematic LC medium is formulated as follows:
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 1000 ppm of the compound of the Formula H-3-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M5, without affecting the remaining physical properties of the mixture M5. 3
  • Example M6 A nematic LC medium is formulated as follows: Mixture Example S6 (stabilised with compound of Formula ST-2-3) A nematic LC mixture according to the invention is formulated as follows: Addition of 500 ppm of the compound of the Formula ST-2-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M6, without affecting the remaining physical properties of the mixture M6.
  • Example M7 A nematic LC medium is formulated as follows: Mixture Example S7 (stabilised with compound of Formula H-3-4) A nematic LC mixture according to the invention is formulated as follows: Addition of 50 ppm of the compound of the Formula H-3-4 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M7, without affecting the remaining physical properties of the mixture M7. 4
  • Example M8 A nematic LC medium is formulated as follows:
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 50 ppm of the compound of the Formula H-3-2 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M8, without affecting the remaining physical properties of the mixture M8.
  • Example M9 A nematic LC medium is formulated as follows: Mixture Example S9 (stabilised with compound of Formula H-3-6) A nematic LC mixture according to the invention is formulated as follows: Mixture M9 99.995 wt.-% Compound of 50 ppm Formula H-3-6 Addition of 50 ppm of the compound of the Formula H-3-6 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M9, without affecting the remaining physical properties of the mixture. 6
  • Example M10 A nematic LC medium is formulated as follows:
  • Example S10 (stabilised with compounds of Formulae ST-2-3 and H-3-3)
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 150 ppm of the compound of the Formula H-3-3 and 500 ppm of the compound of the Formula ST-2-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M10, without affecting the remaining physical properties of the mixture.
  • Example M11 A nematic LC medium is formulated as follows:
  • Mixture Example S11 (stabilised with compound of Formula ST-4-2) A nematic LC mixture according to the invention is formulated as follows: Addition of 1000 ppm of the compound of the Formula ST-4-2 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M11, without affecting the remaining physical properties of the mixture M11. 2
  • Example M12 A nematic LC medium is formulated as follows: Mixture Example S12 (stabilised with compound of Formula ST-1-3)
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 500 ppm of the compound of the Formula ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M12, without affecting the remaining physical properties of the mixture M12.
  • a nematic LC mixture according to the invention is formulated as follows: Addition of the compounds of Formulae ST-4-1, ST-4-2 and ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M12, without affecting the remaining physical properties.
  • Example M14 A nematic LC medium is formulated as follows: Mixture Example S14 (stabilised with compound of Formula H-3-5 and a Compound of Formula ST-1-3) A nematic LC mixture according to the invention is formulated as follows: Addition of 50 ppm of the compound of the Formula H-3-5 and 500 ppm of the compound of the Formula ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M14, without affecting the remaining physical properties of the mixture M14.
  • Example M15 A nematic LC medium is formulated as follows: Mixture Example S15 (stabilised with compound of Formula H-3-7) A nematic LC mixture according to the invention is formulated as follows: Addition of 500 ppm of the compound of the Formula H-3-7 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M15, without affecting the remaining physical properties of the mixture M15. 7
  • Example M16 A nematic LC medium is formulated as follows:
  • Example S17 (stabilised with compound of Formula H-3-1 and a Compound of Formula ST-1-3)
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 1000 ppm of the compound of the Formula H-3-1 and 500 ppm of the compound of the Formula ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M17, without affecting the remaining physical properties of the mixture M17.
  • Example M18 A nematic LC medium is formulated as follows: Mixture Example S18 (stabilised with compound of Formula H-3-1 and a Compound of Formula ST-2-3) A nematic LC mixture according to the invention is formulated as follows: Addition of 1000 ppm of the compound of the Formula H-3-1 and 500 ppm of the compound of the Formula ST-2-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M18, without affecting the remaining physical properties of the mixture M18.
  • Example M19 A nematic LC medium is formulated as follows: N -F Mixture Example S19 (stabilised with compound of Formula H-3-1 and a Compound of Formula ST-4-2) A nematic LC mixture according to the invention is formulated as follows: Addition of 1000 ppm of the compound of the Formula H-3-1 and 500 ppm of the compound of the Formula ST-4-2 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M19, without affecting the remaining physical properties of the mixture M19.
  • Example M20 A nematic LC medium is formulated as follows: F Mixture Example S20 (stabilised with compound of Formula H-3-3 and a Compound of Formula ST-1-3) A nematic LC mixture according to the invention is formulated as follows: Addition of 700 ppm of the compound of the Formula H-3-3 and 500 ppm of the compound of the Formula ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M20, without affecting the remaining physical properties of the mixture M20.
  • Example M21 A nematic LC medium is formulated as follows:
  • Example S21 (stabilised with compound of Formula H-3-3 and a Compound of Formula ST-2-3)
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 700 ppm of the compound of the Formula H-3-3 and 500 ppm of the compound of the Formula ST-2-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M21, without affecting the remaining physical properties of the mixture M21.
  • Example M22 A nematic LC medium is formulated as follows:
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 700 ppm of the compound of the Formula H-3-3 and 500 ppm of the compound of the Formula ST-4-2 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M22, without affecting the remaining physical properties of the mixture M22.
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 50 ppm of the compound of the Formula H-3-6 and 500 ppm of the compound of the Formula ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M25, without affecting the remaining physical properties of the mixture M25.
  • Example M26 A nematic LC medium is formulated as follows: Mixture Example S26 (stabilised with compound of Formula H-3-6 and a Compound of Formula ST-4-2) A nematic LC mixture according to the invention is formulated as follows: Addition of 50 ppm of the compound of the Formula H-3-6 and 500 ppm of the compound of the Formula ST-4-2 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M26, without affecting the remaining physical properties of the mixture M26.
  • Example M27 A nematic LC medium is formulated as follows: Mixture Example S27 (stabilised with compound of Formula H-3-7 and a Compound of Formula ST-1-3) A nematic LC mixture according to the invention is formulated as follows: Addition of 1000 ppm of the compound of the Formula H-3-7 and 500 ppm of the compound of the Formula ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M27, without affecting the remaining physical properties of the mixture M27.
  • Example M28 A nematic LC medium is formulated as follows:
  • Example S28 (stabilised with compound of Formula H-3-7 and a Compound of Formula ST-2-3)
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 1000 ppm of the compound of the Formula H-3-7 and 500 ppm of the compound of the Formula ST-2-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M28, without affecting the remaining physical properties of the mixture M28.
  • Example M29 A nematic LC medium is formulated as follows:
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 1000 ppm of the compound of the Formula H-3-7 and 500 ppm of the compound of the Formula ST-4-2 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M29, without affecting the remaining physical properties of the mixture M29.
  • Example M30 A nematic LC medium is formulated as follows: Mixture Example S30 (stabilised with compound of Formula H-3-9 and a Compound of Formula ST-1-3) A nematic LC mixture according to the invention is formulated as follows: Addition of 50 ppm of the compound of the Formula H-3-9 and 500 ppm of the compound of the Formula ST-1-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M30, without affecting the remaining physical properties of the mixture M30.
  • Example M31 A nematic LC medium is formulated as follows:
  • Example S31 (stabilised with compound of Formula H-3-9 and a Compound of Formula ST-2-3)
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 50 ppm of the compound of the Formula H-3-9 and 500 ppm of the compound of the Formula ST-2-3 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M31, without affecting the remaining physical properties of the mixture M31.
  • Example M32 A nematic LC medium is formulated as follows:
  • Example S32 (stabilised with compound of Formula H-3-9 and a Compound of Formula ST-4-2)
  • a nematic LC mixture according to the invention is formulated as follows: Addition of 50 ppm of the compound of the Formula H-3-9 and 500 ppm of the compound of the Formula ST-4-2 significantly improves the VHR 100 after UV exposure compared to the non-stabilized mixture M32, without affecting the remaining physical properties of the mixture M32.

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Abstract

La présente invention concerne des milieux à cristaux liquides (LC) ou des matériaux LC et des dispositifs d'affichage à cristaux liquides à économie d'énergie (LCD) contenant ces milieux, en particulier des dispositifs d'affichage de jeux et des casques AR/VR adressés par une matrice active et en particulier des dispositifs d'affichage LC du type TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, HB-FFS, XB-FFS, PS-FFS, SA-HB-FFS, SA-XB-FFS, SA-HB-FFS stabilisée par polymère, SA-XB-FFS stabilisée par polymère, VA positif ou PS-VA positif.
PCT/EP2025/056724 2024-03-15 2025-03-12 Milieu à cristaux liquides Pending WO2025190996A1 (fr)

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