WO2023052283A1 - Milieu à cristaux liquides - Google Patents

Milieu à cristaux liquides Download PDF

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WO2023052283A1
WO2023052283A1 PCT/EP2022/076623 EP2022076623W WO2023052283A1 WO 2023052283 A1 WO2023052283 A1 WO 2023052283A1 EP 2022076623 W EP2022076623 W EP 2022076623W WO 2023052283 A1 WO2023052283 A1 WO 2023052283A1
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compounds
atoms
formula
independently
alkyl
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PCT/EP2022/076623
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Chang-Suk Choi
Jing Wang
Ji-Hun Jung
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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
    • 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
    • C09K19/062—Non-steroidal liquid crystal compounds containing one non-condensed benzene ring
    • 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
    • C09K19/3098—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
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/122—Ph-Ph
    • 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
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3004—Cy-Cy
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/301—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 invention relates to a liquid-crystalline medium with negative dielectric anisotropy and to the use thereof for an active-matrix display, in particular based on the VA, SA-VA, IPS, PS-IPS, FFS, PS-FFS, UB-FFS or PS-UB- FFS effect.
  • Media of this type can be used, in particular, for electro-optical displays having active-matrix addressing based on the ECB effect and for IPS (in-plane switching) displays or FFS (fringe field switching) displays.
  • IPS in-plane switching
  • FFS far-field switching
  • liquid-crystalline phases must have high values for the ratio of the elastic constants K 3 /K 1 , high values for the optical anisotropy ⁇ n and values for the dielectric anisotropy of ⁇ ⁇ -0.5 in order to be suitable for use in high-information display elements based on the ECB effect.
  • Dielectrically negative liquid-crystal media can also be used in displays which use the so-called IPS or FFS effect.
  • VAN vertical aligned nematic displays
  • MVA multi-domain vertical alignment, for example: Yoshide, H. et al., paper 3.1: "MVA LCD for Notebook or Mobile PCs ", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp.6 to 9, and Liu, C.T.
  • TFTs metal oxide semiconductor transistors on a silicon wafer as substrate 2.
  • TFTs thin-film transistors
  • the electro-optical effect used is usually dynamic scattering or the guest-host effect.
  • the use of single-crystal silicon as substrate material restricts the display size, since even modular assembly of various part-displays results in problems at the joints.
  • the electro- optical effect used is usually the TN effect.
  • TFTs comprising compound semiconductors, such as, for example, CdSe, or TFTs based on polycrystalline or amorphous silicon. The latter technology is being worked on intensively worldwide.
  • the TFT matrix is applied to the inside of one glass plate of the display, while the other glass plate carries the transparent counterelectrode on its inside. Compared with the size of the pixel electrode, the TFT is very small and has virtually no adverse effect on the image.
  • This technology can also be extended to fully colour-capable displays, in which a mosaic of red, green and blue filters is arranged in such a way that a filter element is opposite each switchable pixel.
  • MLC displays of this type are particularly suitable for TV applications (for example pocket TVs) or for high-information displays in automobile or aircraft construction.
  • TV applications for example pocket TVs
  • high-information displays in automobile or aircraft construction Besides problems regarding the angle dependence of the contrast and the response times, difficulties also arise in MLC displays due to insufficiently high specific resistance of the liquid-crystal mixtures [TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, pp. 141 ff., Paris; STROMER, M., Proc.
  • VA displays have significantly better viewing-angle dependencies and are therefore principally used for televisions and monitors.
  • frame rates image change frequency/repetition rates
  • LC media with negative dielectric anisotropy of prior art for use in FFS mode displays like UB-FFS often do not show sufficiently high reliability, especially when used in high end products such as 8K TV, which can cause problems like short term image sticking or black spot mura.
  • AMLCDs active matrix LC displays
  • WB I/S white black image sticking
  • the invention is based on the object of providing LC media, in particular for monitor and TV applications, which are based on the ECB, IPS or FFS effect, which do not have the above-mentioned disadvantages or only do so to a reduced extent.
  • the LC media for use in monitors and televisions can also operate at extremely high and extremely low temperatures, and at the same time have short response times and improved reliability, and show reduced image sticking, especially reduced white black image sticking, and reduced black spot mura.
  • LC medium as described and claimed hereinafter, wherein a small amount of one or more compounds of formula C having a positive dielectric anisotropy is added to an LC mixture with negative dielectric anisotropy. It was surprisingly found that, compared to LC media without the compounds of formula C or with a higher amount of these compounds, the LC media of the present invention show high reliability, reduced image sticking and black spot mura, while maintaining other desired properties like short response times, high transmittance and low threshold voltage.
  • LC mixtures as disclosed and claimed hereinafter having negative dielectric anisotropy surprisingly results in very low rotational viscosities and in a reduction in the ratio of rotational viscosity and elastic constants, while maintaining a high reliability and high VHR values also after UV exposure, and at the same time show reduced image sticking, especially reduced white black image sticking.
  • the invention further relates to the use of an LC medium as described above and below for electro-optical purposes, in particular for the use in VA, PS-VA, SA-VA, IPS, PS-IPS, FFS, PS-FFS, UB-FFS or PS-UB-FFS displays or in shutter glasses or for 3D applications.
  • the invention further relates to an electro-optical LC display containing an LC medium as described above and below, in particular an VA, PS-VA, SA-VA, IPS, PS-IPS, FFS, PS-FFS, UB-FFS or PS-UB-FFS display.
  • 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 selected from formula C with further LC compounds and optionally with one or more additives.
  • a group R 1-13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L denotes an alkyl radical and/or an alkoxy radical, this may be straight-chain or branched.
  • It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.
  • R 1-13 R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L denotes an alkyl radical wherein one or more CH 2 groups are replaced by S, this may be straight- chain or branched. It is preferably straight-chain, has 1, 2, 3, 4, 5, 6 or 7 C atoms and accordingly preferably denotes thiomethyl, thioethyl, thiopropyl, thiobutyl, thiopentyl, thiohexyl or thioheptyl.
  • R 1-13 R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L denotes an alkoxy or oxaalkyl group it may also contain one or more additional oxygen atoms, provided that oxygen atoms are not linked directly to one another.
  • one or more of R 1-13 , R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L are selected from the group consisting of , , , , , -S 1 -F, -O-S 1 -F, -O-S - 1 1O-S2, wherein S is C1-12-alkylene or C2-12-alkenylene and S 2 is H, C1-12-alkyl or C2-12-alkenyl, and very preferably are selected from the group consisting of , , , , , -OCH 2 OCH 3 , -O(CH 2 ) 2 OCH 3 , -O(CH 2 ) 3 OCH 3 , - O(CH 2 )4OCH 3 , -O(CH 2 ) 2 F, -
  • R 1-13 R 51 , R 52 , R Q , R, R 2A , R 2B , R IIIA , R 1N , R 2N , R B1 , R B2 , R CR1 , R CR2 , R or L denotes an alkyl or alkenyl radical which is at least monosubstituted by halogen, this radical is preferably straight-chain, and halogen is preferably F or Cl. In the case of polysubstitution, halogen is preferably F.
  • the resultant radicals also include perfluorinated radicals.
  • the fluorine or chlorine substituent may be in any desired position, but is preferably in the ⁇ -position.
  • Halogen is preferably F or Cl, very preferably F.
  • substituents L are, for example, F, Cl, CN, NO 2 , CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , COCH 3 , COC 2 H 5 , COOCH 3 , COOC 2 H 5 , CF 3 , OCF 3 , OCHF 2 , OC 2 F 5 , furthermore phenyl. is preferably in which L has one of the meanings indicated above.
  • the LC media according to the invention preferably exhibit very broad nematic phase ranges having clearing points ⁇ 70°C, preferably ⁇ 74°C, very favourable values for the capacitive threshold, relatively high values for the holding ratio and at the same time very good low-temperature stabilities at -20°C and -30°C, as well as very low rotational viscosities and short response times.
  • the LC media according to the invention are furthermore distinguished by the fact that, in addition to the improvement in the rotational viscosity ⁇ 1 , high reliability and high VHR values, even after UV exposure, can be achieved.
  • the LC media according to the invention are furthermore distinguished by the fact that, in addition to the improvement in the rotational viscosity ⁇ 1 , relatively high values of the elastic constant K 3 for improving the response times can be observed.
  • the mixtures according to the invention have a particularly low value for the ratio ⁇ 1 /K 3 of rotational viscosity ⁇ 1 and elastic constant K 3 , which is an indicator of a fast response time.
  • the LC media according to the invention do surprisingly show high reliability and high VHR values also after UV exposure, and at the same time show reduced image sticking, especially reduced white black image sticking, even when containing only a small amount of the compounds of formula I.
  • R 1 denotes preferably alkyl or alkoxy having 1 to 9, preferably 1 to 6, C atoms, all of which are optionally fluorinated or an cycloalkyl ring having 3, 4 or 5 carbon atoms, very preferably ethyl, n-propyl or n-butyl, most preferably ethyl.
  • Preferred compounds of formula C are selected from the following formula: wherein R 1 has one of the meanings of formula C or one of its preferred meanings given above and below, and is preferably ethyl, n-propyl or n-butyl, most preferably ethyl.
  • the proportion of compounds of formula C or C1 in the LC medium is from > 0 to ⁇ 15 %, more preferably from >0 to ⁇ 7 %, even more preferably from > 0 to ⁇ 5 %, very preferably from 0.2 to 4 %, most preferably from 0.5 to 4 % by weight.
  • the LC medium contains 1, 2 or 3, most preferably 1, compounds of formula C or C1.
  • the LC medium comprises one or more compounds of formula II: wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings R 1 and R 2 straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl, preferably alkyl or alkoxy having 1 to 6 C atoms, A 1 and A 2 a group selected from the following formulae: preferably from formulae A1, A2, A3, A4, A5, A6, A9 and A10, very preferably from formulae A1, A2, A3, A4, A5, A9 and A10, Z 1 and
  • the LC medium comprises one or more compounds of formula II selected from the group consisting of compounds of the formulae IIA, IIB, IIC and IID: in which R 2A and R 2B each, independently of one another, denote H, an alkyl or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF 3 or at least monosubstituted by halogen, where, in addition, one or more CH 2 groups in these radicals may be replaced by -O-, -S-, , , -C ⁇ C-, -CF 2 O-, -OCF 2 -, -OC-O- or -O-CO- in such a way that O atoms are not linked directly to one another, L 1 to L 4 each, independently of one another, denote F, Cl, CF 3 or CHF 2 , Y denotes H, F, Cl, CF 3 , CHF 2 or CH 3 , preferably H or CHCH
  • Preferred compounds of the formulae IIA, IIB, IIC and IID are those wherein R 2B denotes an alkyl or alkoxy radical having up to 15 C atoms, and very preferablydenotes (O)C v H 2v+1 wherein (O) is an oxygen atom or a single bond and v is 1, 2, 3, 4, 5 or 6.
  • R 2A or R 2B denotes or contains cycloalkyl or cycloalkoxy radical, preferably selected from the group consisting of , , wherein S 1 is C 1-5 - alkylene or C 2-5 -alkenylene and S 2 is H, C 1-7 -alkyl or C 2-7 -alkenyl, and very preferably selected from the group consisting of , , Further preferred compounds of the formulae IIA, IIB, IIC and IID are indicated below:
  • alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms
  • alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms
  • (O) denotes an oxygen atom or a single bond.
  • the LC medium comprises one or more compounds selected from the formulae IIA and IIB and their subformulae. In another preferred embodiment the LC medium comprises one or more compounds of the formula IIC or its subformulae. In another preferred embodiment the LC medium comprises one or more compounds of the formula IID or its subformulae.
  • Particularly preferred LC medium according to the invention comprises one or more compounds selected from the group consisting of the formulae IIA-2, IIA-8, IIA-10, IIA-16, II-18, IIA-40, IIA-41, IIA-42, IIA-43, IIB-2, IIB-10, IIB-16, IIC-1, and IID-4, most preferably selected from the group consisting of the formulae IIA-2, IIA-10, IIB-10, IIC-1 and IID-4.
  • the proportion of compounds of the formulae IIA and/or IIB in the mixture as a whole is preferably at least 20 % by weight.
  • the proportion of compounds of the formula IIC in the mixture as a whole is preferably from 0.5 to 10 %, more preferably from 0.5 to 5 %, most preferably from 1 to 3 % by weight.
  • the proportion of compounds of the formula IID in the mixture as a whole is preferably from 2 to 40 %, more preferably from 5 to 25 % by weight.
  • R 11 and R 12 each, independently of one another, an alkyl, alkenyl or alkoxy radical having up to 15 C atoms, more preferably one or both of them denote an alkoxy radical and L 11 and L 12 each denote F.
  • R 1 and R 2 denote straight-chain alkoxy having 1-6 C atoms, very preferably ethoxy, propoxy, butoxy, pentoxy or hexoxy.
  • R 1 denotes very preferably ethoxy or propoxy, most preferably propoxy.
  • R 2 denotes very preferably ethoxy, propoxy, butoxy, pentoxy or hexoxy, most preferably butoxy, pentoxy or hexoxy.
  • the LC medium comprises one or more compounds of the formula III-1 selected from the group consisting of formulae III-1-1 to III-1-10, preferably of formula III-1-6:
  • the LC medium comprises one or more compounds of the formula III-2 or its subformulae.
  • the LC medium comprises one or more compounds of the formula III-2 selected from the group consisting of formulae III-2-1 to III-2-10, preferably of formula III-2-6:
  • alkyl and “alkyl*” each, independently of one another denote a straight-chain alkyl radical having 1-6 C atoms
  • alkenyl and “alkenyl*” each, independently of one another denote a straight-chain alkenyl radical having 2-6 C atoms
  • alkoxy and “alkoxy*” each, independently of one another denote a straight-chain alkoxy radical having 1-6 C atoms
  • L 11 and L 12 each, independently of one another, denote F or Cl, preferably both F.
  • the LC medium comprises one or more compounds selected from the group consisting of the following formulae:
  • the LC medium comprises one or more compounds of the formula IIIA-1 and/or IIIA-2: in which L 11 and L 12 have the same meanings as given under formula III, (O) denotes O or a single bond, R IIIA denotes alkyl or alkenyl having up to 7 C atoms or a group Cy- C m H 2m+1 -, L 11 and L 12 each, independently of one another, denote F, Cl, CF 3 or CHF 2 , preferably H or F, most preferably F, and m and n are, identically or differently, 0, 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, very preferably 1, and Cy denotes a cycloaliphatic group having 3, 4 or 5 ring atoms, which is optionally substituted with alkyl or alkenyl each having up to 3 C atoms, or with halogen or CN, and
  • the compounds of formula IIIA-1 and/or IIIA-2 are contained in the LC medium either alternatively or additionally to the compounds of formula III, preferably additionally.
  • Very preferred compounds of the formulae IIIA-1 and IIIA-2 are the following: in which alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms.
  • Particularly preferred compounds of formula IIIA-2 are the following:
  • the compounds of formula III-3 are preferably selected from the group of compounds of the formulae III-3-1 to III-3-10: in which R 12 denotes alkyl having 1 to 7 C-atoms, preferably ethyl, n-propyl or n-butyl, or alternatively cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl.
  • the LC medium comprises one or more compounds of the formulae III-4 to III-6, preferably of formula III-5: in which the parameters have the meanings given above, R 11 preferably denotes straight-chain alkyl and R 12 preferably denotes alkoxy, each having 1 to 7 C atoms.
  • the LC medium comprises one or more compounds of the formula I selected from the group of compounds of formulae III-7 to III-9, preferably of formula III-8: in which the parameters have the meanings given above, R 11 preferably denotes straight-chain alkyl and R 12 preferably denotes alkoxy each having 1 to 7 C atoms.
  • the LC medium contains one or more compounds selected from the group consisting of formulae III-1 and III-2.
  • the LC medium contains 1, 2 or 3 compounds of formula III or its subformulae.
  • the LC medium contains one or more compounds of formula III-2.
  • the total proportion of the compounds of formula III and its subformulae in the LC medium is from 2 to 20%, very preferably from 5 to 15% by weight.
  • the medium comprises one or more compounds of the formula IV: in which R 41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms, preferably an n-alkyl radical, particularly preferably having 2, 3, 4 or 5 C atoms, and R 42 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkoxy radical having 1 to 6 C atoms, both preferably having 2 to 5 C atoms, an 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 or an unsubstituted alkenyl radical having 2 to 7 C atoms, preferably an n-
  • 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-1-4:
  • the LC medium according to the invention comprises one or more compounds of the formulae IV-2-1 and/or IV-2-2: In another preferred embodiment, the LC medium according to the invention comprises a compound of formula IV-3, in particular selected from the compounds of the formulae IV-3-1 to IV-3-4
  • the LC medium according to the invention comprises a compound of formula IV-3-1 and/or a compound of formula IV-3-3.
  • the LC medium according to the invention comprises a compound of formula IV-4, in particular selected from the compounds of the formulae IV-4-1 and IV-4-2:
  • the LC medium according to the invention preferably comprises at least one compound of the formula IVa-1and/or formula IVa-2.
  • the LC medium comprises one or more compounds of formula IVb-1 to IVb-3: in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1 to 6 C atoms, and alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2 to 6 C atoms.
  • the proportion of the biphenyls of the formulae IV-1 to IV-3 in the mixture as a whole is preferably at least 3 % by weight, in particular ⁇ 5 % by weight.
  • the compounds of the formula IVb-2 are particularly preferred.
  • Particularly preferred biphenyls are the following: 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 comprises 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
  • the LC medium according to the invention very particularly preferably com- prises the compounds of the formula V-10, V-12, V-16 and/or IV-1, in particular in amounts of 5 to 30 %.
  • Preferred compounds of the formulae V-10 are indicated below:
  • the LC medium according to the invention particularly preferably 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 %.
  • the LC medium comprises the compounds of formulae 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 15 to 35 %, particularly preferably 15 to 25 % and especially preferably 18 to 22 %, based on the mixture as a whole.
  • the LC medium comprises the compounds of formulae V-10b and/or IV-1-1:
  • the compounds V-10b and IV-1-1 are preferably present in the mixture in a concentration of 15 to 35 %, particularly preferably 15 to 25 % and especially preferably 18 to 22 %, based on the mixture as a whole.
  • a very particularly preferred LC medium comprises the compounds of the following three formulae:
  • the compounds V-10a, V-10b and IV-1-1 are preferably present in the mixture in a concentration of 15 to 35 %, particularly preferably 15 to 25 % and especially preferably 18 to 22 %, based on the mixture as a whole.
  • a preferred LC medium comprises at least one compound selected from the group consisting of the following compounds: in which R 41 and R 42 , and R 51 and R 52 have the meanings indicated above.
  • R 41 and R 51 denotes alkyl or alkenyl having 1 to 6 or 2 to 6 C atoms, respectively
  • R 42 and R 52 denotes alkenyl having 2 to 6 C atoms.
  • the LC medium comprises at least one compound selected from the group consisting of the formulae V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a and IV-3b: in which alkyl denotes an alkyl radical having 1 to 6 C atoms and alkenyl denotes an alkenyl radical having 2 to 6 C atoms.
  • the compounds of the formulae V-6a, V-6b, V-7a, V-7b, IV-4-1, IV-4-2, IV-3a and IV-3b are preferably present in the LC medium according to the invention in amounts of 1 to 40 % by weight, preferably 5 to 35 % by weight and very particularly preferably 10 to 30 % by weight.
  • the LC medium additionally comprises one or more compounds of the formulae VI-1 to VI-9:
  • R 7 each, independently of one another, have one of the meanings indicated for R 2A in formula IIA, and w and x each, independently of one another, denote 1 to 6.
  • LC medium comprising at least one compound of the formula V-9.
  • the LC medium additionally comprises one or more compounds of the formulae VII-1 to VII-25:
  • R denotes a straight-chain alkyl or alkoxy radical having 1 to 6 C atoms, (O) denotes -O- or a single bond, X denotes F, Cl, OCF 3 or OCHF 2 , L x denotes H or F, m is 0, 1, 2, 3, 4, 5 or 6 and n is 0, 1, 2, 3 or 4.
  • R preferably denotes methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy.
  • X preferably denotes F or OCH 3 , very preferably F.
  • the LC medium according to the invention preferably comprises the ter- phenyls of the formulae VII-1 to VII-25 in amounts of 2 to 30 % by weight, in particular 5 to 20 % by weight.
  • Particular preference is given to compounds of the formulae VII-1, VII-2, VII-4, VII-20, VII-21, and VII-22 wherein X denotes F.
  • R preferably denotes alkyl, furthermore alkoxy, each having 1 to 5 C atoms.
  • R preferably denotes alkyl or alkenyl, in particular alkyl.
  • R preferably denotes alkyl.
  • X preferably denotes F.
  • terphenyls of formula VII-1 to VII-25 are preferably employed in the LC medium according to the invention if the ⁇ n value of the mixture is to be ⁇ 0.1.
  • Preferred LC media comprise 2 to 20 % by weight of one or more terphenyl compounds selected from the group of the compounds of formulae VII-1 to VII-25. Further preferred embodiments according to the invention are listed below: a) LC medium comprising at least one compound of the formulae Z-1 to Z-7:
  • LC medium comprising one or more substances which contain a tetrahydronaphthyl or naphthyl unit, such as, for example, the compounds of the formulae N-1 to N-5:
  • LC medium comprising one or more compounds selected from the group of the difluorodibenzochroman compounds of the formula BC, chromans of the formula CR, and fluorinated phenanthrenes of the formulae PH-1 and PH-2: in which R B1 , R B2 , R CR1 , R CR2 , R 1 , R 2 each, independently of one another, have the meaning of R 2A .
  • c is 0, 1 or 2.
  • R 1 and R 2 preferably, independently of one another, denote alkyl or alkoxy having 1 to 6 C atoms.
  • the LC mediaumaccording 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.
  • LC media comprising one, two or three compounds of the formula BC-2, BF-1 and/or BF-2.
  • LC medium comprising one or more indane compounds of the formula In:
  • R 11 , R 12 , R 13 each, independently of one another, denote a straight- chain alkyl, alkoxy, alkoxyalkyl or alkenyl radical having 1 to 6 C atoms
  • R 12 and R 13 additionally denote halogen, preferably F, denotes 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 comprising one or more compounds of the formulae L-1 to L-5:
  • R and R 1 each, independently of one another, have the meanings indicated for R 2A in formula IIA above, and alkyl denotes an alkyl radical having 1 to 6 C atoms.
  • the parameter s denotes 1 or 2.
  • the compounds of the formulae L-1 to L-5 are preferably employed in concentrations of 5 to 50 % by weight, in particular 5 to 40 % by weight and very particularly preferably 10 to 40 % by weight.
  • LC medium comprising one or more compounds of formula IIA-Y in which R 11 and R 12 have one of the meanings given for R 2A in formula IIA above, and L 1 and L 2 , identically or differently, denote F or Cl.
  • Preferred compounds of the formula IIA-Y are selected from the group consisting of the following subformulae: in which, Alkyl and Alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, Alkoxy and Alkoxy* 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 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 formula IIA-Y6a.
  • LC medium comprising one or more quaterphenyl compounds selected from the following formula:
  • 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.
  • the compounds of formula Q are preferably selected from the following subformulae:
  • R Q has one of the meanings of formula Q or one of its preferred meanings given above and below, and is preferably ethyl, n-propyl or n- butyl. Especially preferred are compounds of formula Q1, in particular those wherein R Q is n-propyl.
  • the proportion of compounds of formula Q in the LC medium is from >0 to ⁇ 5% by weight, very preferably from 0.05 to 2% by weight, more preferably from 0.1 to 1% by weight, most preferably from 0.1 to 0.8% by weight.
  • the LC medium contains 1 to 5, preferably 1 or 2 compounds of formula Q.
  • quaterphenyl compounds of formula Q to the LC host mixture enables to reduce ODF mura, whilst maintaining high UV absorption, enabling quick and complete polymerization, enabling strong and quick tilt angle generation, and increasing the UV stability of the LC medium.
  • compounds of formula Q which have positive dielectric anisotropy, 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 C, preferably of formula C1, in a total concentration in the range from 0.5 to 10 %, more preferably from 0.5 to 8 % by weight, most preferably from 1 to 6 % by weight; and/or - one or more compounds of formula IIA, preferably of formula IIA-2 or IIA-10, preferably in a total concentration in the range of from 4 % to 25 %, more preferably from 5 % to 20 %, most preferably from 6 % to 15 % by weight; and/or - one or more compounds of formulae IIA and IIB, preferably of formulae IIA- 2 and/or IIA-10 and/or IIB-10, in a total concentration in the range of from 5 % to 25 %, more preferably from 10 to 20 % by weight; and/or - one or more compounds of formula IIC, preferably of formula IIC-1, preferably in a total concentration in the range of from 0.5 % to 10 %, more
  • the invention furthermore relates to an electro-optical display having active- matrix addressing, characterised in that it contains, as dielectric, a LC medium according to claim 1 and wherein the display is a VA, SA-VA, IPS, U-IPS, FFS, UB-FFS, SA-FFS, PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB- FFS, PS-posi-VA, PS-TN, polymer stabilised SA-VA or polymer stabilised SA-FFS display.
  • the LC medium has preferably a nematic LC phase.
  • the LC medium according to the invention preferably have a nematic phase from ⁇ -20°C to ⁇ 70°C, particularly preferably from ⁇ -30°C to ⁇ 75°C, very particularly preferably from ⁇ -40°C to ⁇ 80°C.
  • the medium according to the invention preferably has a clearing temperature of 70°C or more, preferably of 80°C or more.
  • the expression "have a nematic phase” here means on the one hand that no smectic phase and no crystallisation are observed at low temperatures at the corresponding temperature and on the other hand that clearing still does not occur on heating from the nematic phase.
  • the investigation at low temperatures is carried out in a flow viscometer at the corresponding tem- perature and checked by storage in test cells having a layer thickness cor- responding to the electro-optical use for at least 100 hours. If the storage stability at a temperature of -20°C in a corresponding test cell is 1000 h or more, the medium is referred to as stable at this temperature. At tempera- tures of -30°C and -40°C, the corresponding times are 500 h and 250 h respectively. At high temperatures, the clearing point is measured by con- ventional methods in capillaries.
  • the liquid-crystal mixture preferably has a nematic phase range of at least 60 K and a flow viscosity ⁇ 20 of at most 30 mm 2 ⁇ s -1 at 20°C.
  • the mixture is nematic at a temperature of -20°C or less, preferably at -30°C or less, very preferably at -40°C or less.
  • the values of the birefringence ⁇ n in the liquid-crystal mixture are generally between 0.07 and 0.16, preferably between 0.08 and 0.15, very preferably between 0.09 and 0.14.
  • the medium has a birefringence in the range of from 0.0850 to 0.110, preferably from 0.090 to 0.1050.
  • the liquid-crystal mixture according to the invention has a dielectric anisotropy ⁇ of -1.5 to -8.0, preferably of -2.0 to – 4.0, in particular -2.5 to -3.5,
  • the rotational viscosity ⁇ 1 at 20°C is preferably ⁇ 110 mPa ⁇ s, in particular ⁇ 100 mPa ⁇ s.
  • the rotational viscosity ⁇ 1 at 20°C is ⁇ 95mPa ⁇ s, in particular ⁇ 90 mPa ⁇ s.
  • the liquid-crystal media according to the invention have relatively low values for the threshold voltage (V 0 ).
  • the term "threshold voltage” relates to the capa- citive threshold (V 0 ), also called the Freedericks threshold, unless explicitly indicated otherwise.
  • the liquid-crystal media according to the invention have high values for the voltage holding ratio in liquid-crystal cells. In general, liquid-crystal media having a low addressing voltage or 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 com- pounds denotes those having -1.5 ⁇ ⁇ ⁇ 1.5
  • dielectrically negative compounds denotes those having ⁇ ⁇ -1.5.
  • the dielectric ani- sotropy of the compounds is determined here by dissolving 10 % of the compounds in a LC host and determining the capacitance of the resultant mixture in at least one test cell in each case having a layer thickness of 20 ⁇ m with homeotropic and with homogeneous surface alignment at 1 kHz.
  • the measurement voltage is typically 0.5 V to 1.0 V, but is always lower than the capacitive threshold of the respective liquid-crystal mixture investigated.
  • the LC media according to the invention are suitable for all VA-TFT (vertical alignment-thin film transistor) applications, such as, for example, VAN (vertically aligned nematic), MVA (multidomain VA), (S)-PVA (super patterned VA), ASV (advanced super view, or axially symmetric VA), PSA (polymer sustained VA) and PS-VA (polymer stabilized VA). They are fur- thermore suitable for IPS (in-plane switching) and FFS (fringe field switching) applications having negative ⁇ .
  • VA-TFT vertical alignment-thin film transistor
  • Component A has significantly negative dielectric anisotropy and gives the nematic phase a dielectric anisotropy of ⁇ -0.5.
  • it preferably comprises the compounds of the for- mulae IIA, IIB and/or IIC, furthermore one or more compounds of the formula IV-1.
  • the proportion of component A is preferably between 45 and 100 %, in par- ticular between 60 and 85 %.
  • one (or more) individual compound(s) which has (have) a value of ⁇ ⁇ -0.8 is (are) preferably selected. This value must be more negative, the smaller the proportion A in the mixture as a whole.
  • Component B has pronounced nematogeneity and a flow viscosity of not greater than 30 mm 2 ⁇ s -1 , preferably not greater than 25 mm 2 ⁇ s -1 , at 20°C.
  • a multiplicity of suitable materials is known to the person skilled in the art from the literature. Particular preference is given to compounds of the formula O-17.
  • Particularly preferred individual compounds in component B are extremely low-viscosity nematic liquid crystals having a flow viscosity of not greater than 18 mm 2 ⁇ s -1 , preferably not greater than 12 mm 2 ⁇ s -1 , at 20°C.
  • Component B is monotropically or enantiotropically nematic, has no smectic phases and is able to prevent the occurrence of smectic phases down to very low temperatures in LC media.
  • the nemato- geneity of these materials can be compared through the degree of sup- pression of smectic phases that is achieved.
  • the mixture may optionally also comprise a component C, comprising compounds having a dielectric anisotropy of ⁇ ⁇ 1.5.
  • the medium preferably comprises 4 to 15, in particular 5 to 12, and particularly preferably ⁇ 10, compounds of the formulae IIA, IIB, IIC and/or IID, 1 to 5, preferably 1, 2 or 3, compounds of the formula III, and optionally one or more compounds of the formula IV.
  • the other constituents are preferably selected from nematic or nematogenic substances, in particular known substances, from the classes of the azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl or cyclo- hexyl benzoates, phenyl or cyclohexyl cyclohexanecarboxylates, phenyl- cyclohexanes, cyclohexylbiphenyls, cyclohexylcyclohexanes, cyclo- hexylnaphthalenes, 1,4-biscyclohexylbiphenyls or cyclohexylpyrimidines, phenyl- or cyclohexyldioxanes, optionally halogenated stilbenes, benzyl phenyl ethers, tolanes and substituted cinnamic acid esters.
  • R 20 and R 21 are different from one another, one of these radicals usually being an alkyl or alkoxy group.
  • Other variants of the proposed substituents are also common. Many such substances or also mixtures thereof are commercially available. All these substances can be prepared by methods known from the literature. It goes without saying for the person skilled in the art that the VA, IPS or FFS mixture according to the invention may also comprise compounds in which, for example, H, N, O, Cl and F have been replaced by the corresponding isotopes.
  • the combination of compounds of the preferred embodiments mentioned above with the polymerized compounds described above causes low threshold voltages, low rotational viscosities and very good low-temperature stabilities in the LC media according to the invention at the same time as constantly high clearing points and high HR values, and allows the rapid establishment of a particularly low tilt angle (i.e. a large tilt) in PSA displays.
  • the LC media exhibit significantly shortened response times, in particular also the grey-shade response times, in PSA displays compared with the LC media from the prior art.
  • the LC media according to the invention may also comprise further additives which are known to the person skilled in the art and are described in the literature, such as, for example, polymerization initiators, inhibitors, stabilisers, surface-active substances or chiral dopants. These may be polymerizable or non-polymerizable.
  • the LC medium additionally comprises one or more polymerizable compounds.
  • Particularly preferred compounds of the formula I are those in which B 1 and B 2 each, independently of one another, denote 1,4-phenylene, 1,3- phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7- diyl, 9,10-dihydro-phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7- diyl, coumarine, flavone, where, in addition, one or more CH groups in these groups may be replaced by N, cyclohexane-1,4-diyl, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by O and/or S, 1,4- cyclohexenylene, bicycle[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, s
  • Particularly preferred compounds of the formula M are those in which B 1 and B 2 each, independently of one another, denote 1,4-phenylene, 1,3- phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl.
  • Very preferred compounds of formula M are selected from the following formulae:
  • P 1 , P 2 , P 3 a polymerizable group, preferably selected from vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxy,
  • R aa one or more of the radicals P 1 -Sp 1 -, P 1 -Sp 2 - and P 3 -Sp 3 - may denote R aa , with the proviso that at least one of the radicals P 1 -Sp 1 -, P 2 -Sp 2 and P 3 -Sp 3 - present is different from R aa , preferably -(CH 2 ) P I-, -(CH 2 ) P I-O-, -(CH 2 ) P I-CO-O- or -(CH 2 ) P I- O-CO-O-, wherein p1 is an integer from 1 to 12,
  • R aa H, F, Cl, CN or straight-chain or branched alkyl having 1 to
  • compounds of formulae M2 and M13 especially direactive compounds containing exactly two polymerizable groups P 1 and P 2 .
  • compounds selected from formulae M17 to M32 in particular from formulae M17, M22, M24, M27, M30 and M32, especially trireactive compounds containing exactly three polymerizable groups P 1 , P 2 and P 3 .
  • the group wherein L on each occurrence, identically or differently, has one of the meanings given above or below, and is preferably F, Cl, CN, NO 2 , CH 3 , C 2 H 5 , C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(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 or P-Sp-, very preferably F, Cl, CN, CH 3 , C 2 H 5 , OCH 3 , COCH 3 , OCF 3 or P-Sp-, more preferably F, Cl, CH 3 , OCH 3 , COCH 3 or OCF 3 , most preferably F or OCH 3 .
  • Preferred compounds of formulae M1 to M32 are those wherein P 1 , P 2 and P 3 denote an acrylate, methacrylate, oxetane or epoxy group, very preferably an acrylate or methacrylate group, most preferably a methacrylate group. Further preferred compounds of formulae M1 to M32 are those wherein Sp 1 , Sp 2 and Sp 3 are a single bond. Further preferred compounds of formulae M1 to M32 are those wherein one of Sp 1 , Sp 2 and Sp 3 is a single bond and another one of Sp 1 , Sp 2 and Sp 3 is different from a single bond.
  • Further preferred compounds of formulae M1 to M32 are those wherein those groups Sp 1 , Sp 2 and Sp 3 that are different from a single bond denote - (CH 2 ) s1 -X"-, wherein s1 is an integer from 1 to 6, preferably 2, 3, 4 or 5, and X" is X" is the linkage to the benzene ring and is -O-, -O-CO-, -CO-O, -O-CO- O- or a single bond.
  • Further preferred compounds of formula M are those selected from Table D below, especially those selected from the group consisting of formulae 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-183.
  • LC media comprising one, two or three polymerizable compounds of formula M.
  • LC media comprising two or more direactive polymerizable compounds of formula M, preferably selected from formulae M1 to M16, very preferably selected from formulae M2 and M13.
  • LC media comprising one or more direactive polymerizable compounds of formula M, preferably selected from formulae M1 to M16, very preferably from formulae M2 and M13, and one or more trireactive polymerizable compounds of formula M, preferably selected from formulae M17 to M32, very preferably from formulae M20, M22, M24, M27, M30 and M32.
  • LC media comprising one or more polymerizable compounds of formula M wherein at least one r is not 0, or at least one of s and t is not 0, very preferably selected from formulae M2, M13, M22, M24, M27, M30 and M32, and wherein L is selected from the preferred groups shown above, most preferably from F and OCH 3 .
  • polymerizable compounds are listed in Table D below.
  • polymerizable compounds which show absorption in the wavelength range from 320 to 380nm, preferably selected from formula M, very preferably from formulae M1 to M32, more preferably from the group consisting of the above-mentioned formulae from Table D, most preferably from the group consisting of 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-64, RM-74, RM-76, RM-88, RM-102, RM-103, RM-109, RM-117, RM-120, RM-121, RM- 122, R-139, RM-142 and RM-171 to RM-183.
  • formula M very preferably from formulae M1 to M32, more preferably from the group consisting of the above-mentioned formulae from Table D, most preferably from the
  • polymerizable compounds are selected from the compounds used in the mixture examples below.
  • the proportion of polymerizable compounds in the LC medium is from 0.01 to 2%, very preferably from 0.05 to 1%, most preferably from 0.1 to 0.5%.
  • the polymerizable group P is a group which is suitable for a polymerization reaction, such as, for example, free-radical or ionic chain polymerization, polyaddition or polycondensation, or for a polymer-analogous reaction, for example addition or condensation onto a main polymer chain.
  • Sp is different from a single bond, it is preferably of the formula Sp"-X", so that the respective radical P-Sp- conforms to the formula P-Sp"-X"-, wherein Sp" denotes alkylene having 1 to 20, preferably 1 to 12, C atoms, which is optionally mono- or polysubstituted by F, Cl, Br, I or CN and in which, in addition, one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by -O-, -S-, -NH-, -N(R 0 )-, -Si(R 0 R 00 )-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -S-CO-, -CO-S-, -N(R 00 )-CO-O-, -O-CO-N(R 0 )-, -N(R 0 )-CO-N(R 00
  • X" is preferably -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR 0 - CO-, -NR 0 -CO-NR 00 - or a single bond.
  • Typical spacer groups Sp and -Sp"-X"- are, for example, -(CH 2 ) p1 -, - (CH 2 CH 2 O) q1 -CH 2 CH 2 -, -CH 2 CH 2 -S-CH 2 CH 2 -, -CH 2 CH 2 -NH-CH 2 CH 2 - or - (SiR 0 R 00 -O) p1 -, in which p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 0 and R 00 have the meanings indicated above.
  • Particularly preferred groups Sp and -Sp”-X”- are -(CH 2 ) p1 -, -(CH 2 ) p1 -O-, -(CH 2 ) p1 -O-CO-, -(CH 2 ) p1 -CO-O-, -(CH 2 ) p1 -O-CO-O-, in which p1 and q1 have the meanings indicated above.
  • Particularly preferred groups Sp" are, in each case straight-chain, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylenethioethylene, ethylene-N-methylimino- ethylene, 1-methylalkylene, ethenylene, propenylene and butenylene.
  • the polymerizable compounds contained in the LC medium are polymerized or crosslinked (if one compound contains two or more polymerizable groups) by in-situ polymerization in the LC medium between the substrates of the LC display, optionally while a voltage is applied to the electrodes.
  • the structure of the PSA displays according to the invention corresponds to the usual geometry for PSA displays, as described in the prior art cited at the outset. Geometries without protrusions are preferred, in particular those in which, in addition, the electrode on the colour filter side is unstructured and only the electrode on the TFT side has slots. Particularly suitable and preferred electrode structures for PS-VA displays are described, for example, in US 2006/0066793 A1.
  • the LC medium contains one or more polymerization initiators.
  • Suitable conditions for the polymerization and suitable types and amounts of initiators are known to the person skilled in the art and are described in the literature.
  • Suitable for free-radical polymerization are, for example, the commercially available photoinitiators Irgacure651®, Irgacure184®, Irgacure907®, Irgacure369® or Darocure1173® (Ciba AG). If a polymerization initiator is employed, its proportion is preferably 0.001 to 5% by weight, particularly preferably 0.001 to 1% by weight.
  • the polymerizable compounds according to the invention are also suitable for polymerization without an initiator, which is accompanied by considerable advantages, such, for example, lower material costs and in particular less contamination of the LC medium by possible residual amounts of the initiator or degradation products thereof.
  • the polymerization can thus also be carried out without the addition of an initiator.
  • the LC medium does not contain a polymerization initiator.
  • the LC medium additionally comprises one or more stabilisers in order to prevent undesired spontaneous polymerization of the RMs, for example during storage or transport. Suitable types and amounts of stabilisers are known to the person skilled in the art and are described in the literature.
  • the commercially available stabilisers from the Irganox® series (Ciba AG), such as, for example, Irganox® 1076. If stabilisers are employed, their proportion, based on the total amount of RMs or the polymerizable component (com- ponent A), is preferably 10-50,000 ppm, particularly preferably 50-5,000 ppm.
  • the LC medium contains 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 B below, very preferably from the group consisting of R- or S-1011, R- or S-2011, R- or S- 3011, R- or S-4011, and R- or S-5011.
  • the LC media contain a racemate of one or more chiral dopants, which are preferably selected from the chiral dopants mentioned in the previous paragraph.
  • the LC medium may also comprise one or more stabilisers. Suitable types and amounts of stabilisers are known to the person skilled in the art and are described in the literature.
  • stabilisers from the Irganox ® series (Ciba AG), such as, for example, Irganox ® 1076. If stabilisers are employed, their proportion is preferably 10-500,000 ppm, more preferably 50-5,000 ppm, very preferably 50-1,000 ppm.
  • the LC medium contains one or more stabilisers selected from the group consisting of the following formulae: wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings R a-d straight-chain or branched alkyl with 1 to 10, preferably 1 to 6, very preferably 1 to 4 C atoms, most preferably methyl, X S H, CH 3 , OH or O ⁇ , A S straight-chain, branched or cyclic alkylene with 1 to 20 C atoms which is optionally substituted, n an integer from 1 to 6, preferably 3.
  • Preferred stabilisers of formula S3 are selected from formulaS3A:
  • n2 is an integer from 1 to 12, and wherein one or more H atoms in the group (CH 2 )n2 are optionally replaced by methyl, ethyl, propyl, butyl, pentyl or hexyl.
  • Very preferred stabilisers are selected from the group consisting of the following formulae:
  • the LC medium comprises one or more stabilisers selected from the group consisting of formulae S1-1, S2-1, S3-1, S3-1 and S3-3.
  • the LC medium comprises one or more stabilisers selected from Table C below.
  • the proportion of stabilisers, like those of formula S1-S3, 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 contains a self alignment (SA) additive, preferably in a concentration from 0.1 to 5%, very preferably from 0.1 to 3%, more preferably from 0.1 to 2.5 %, most preferably from 0.2 to 1.5%.
  • SA self alignment
  • the SA-VA display according to the present invention does not contain a polyimide alignment layer.
  • the SA-VA display according to preferred embodiment contains a polyimide alignment layer.
  • Preferred SA additives for use in this preferred embodiment are selected from compounds comprising a mesogenic group and a straight-chain or branched alkyl side chain that is terminated with one or more polar anchor groups selected from hydroxy, carboxy, amino or thiol groups. Further preferred SA additives contain one or more polymerizable groups which are attached, optionally via spacer groups, to the mesogenic group. These polymerizable SA additives can be polymerized in the LC medium under similar conditions as applied for the RMs in the PSA process.
  • an LC medium or a polymer stabilised SA- VA display according to the present invention contains one or more self alignment additives selected from Table E below. Preference is given to LC media which have a nematic LC phase, and preferably have no chiral liquid crystal phase.
  • LC media for example, 0 to 15% by weight of pleochroic dyes, furthermore nanoparticles, conductive salts, preferably ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutyl- ammonium tetraphenylborate or complex salts of crown ethers (cf., for example, Haller et al., Mol. Cryst. Liq. Cryst.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, tetrabutyl- ammonium tetraphenylborate or complex salts of crown ethers (cf., for example, Haller et al., Mol. Cryst. Li
  • 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 construction of an LC display according to the invention from polarisers, electrode base plates and surface-treated electrodes corresponds to the usual design for displays of this type.
  • the term usual design is broadly drawn here and also encompasses all derivatives and modifications of the LC display, in particular including matrix display elements based on poly-Si TFTs or MIM.
  • 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.
  • All radicals C n H 2n+1 , C m H 2m+1 , C n H 2n , C m H 2m and C k H 2k are straight-chain alkyl radicals or alkenyl radicals respectively, in each case having n, m or k C atoms; n and m each, independently of one another, denote 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, preferably 1, 2, 3, 4, 5 or 6, and k is 0, 1, 2, 3, 4, 5 or 6.
  • Table I the ring elements of the respective compound are coded, in Table II the bridging members are listed and in Table III the meanings of the symbols for the left- hand and right-hand side chains of the compounds are indicated.
  • Preferred mixture components are shown in Table A below.
  • m and n are independently of each other an integer from 1 to 12, preferably 1, 2, 3, 4, 5 or 6, k is 0, 1, 2, 3, 4, 5 or 6, and (O)C m H 2m+1 means C m H 2m+1 or OC m H 2m+1 .
  • the LC media according to the invention comprise one or more compounds selected from the group consisting of compounds from Table A.
  • Table B shows possible chiral dopants which can be added to the LC media according to the invention.
  • the LC media preferably comprise 0 to 10% by weight, in particular 0.01 to 5% by weight, particularly preferably 0.1 to 3% by weight, of dopants.
  • the LC media preferably comprise one or more dopants selected from the group consisting of compounds from Table B.
  • Table C Table C shows possible 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 C.
  • Table D Table D shows illustrative reactive mesogenic compounds which can be used in the LC media in accordance with the present invention.
  • the mixtures according to the invention comprise one or more polymerizable compounds, preferably selected from the polymerizable compounds of the formulae RM-1 to RM-182.
  • 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-183 are examples of these compounds RM
  • the LC media, SA-VA and SA-FFS displays according to the present invention comprise one or more SA additives selected from formulae SA-1 to SA-48, preferably from formulae SA-14 to SA-48, very preferably from formulae SA-20 to SA-34 and SA-44, in combination with one or more RMs of formula I.
  • SA additives selected from formulae SA-1 to SA-48, preferably from formulae SA-14 to SA-48, very preferably from formulae SA-20 to SA-34 and SA-44, in combination with one or more RMs of formula I.
  • threshold voltage for the present invention relates to the capa- citive threshold (V 0 ), also known as the Freedericks threshold, unless explicitly indicated otherwise.
  • the optical threshold may also, as generally usual, be quoted for 10% relative contrast (V 10 ).
  • the display used for measurement of the capacitive threshold voltage usually consists of two plane-parallel glass outer plates, each of which has on the inside an electrode layer and an unrubbed polyimide alignment layer on top, which effect the desired edge alignment of the liquid-crystal molecules.
  • Example 1 The nematic LC mixture N1 is formulated as follows B(S)-2O-O4 3.00 % cl.p.
  • Example 2 The nematic LC mixture N2 is formulated as follows B(S)-2O-O4 3.00 % cl.p. 82.5°C B(S)-2O-O5 4.00 % ⁇ n 0.0928 B(S)-2O-O6 2.00 % n e 1.5743 CC-3-V 45.00 % n o 1.4815 CC-3-V1 4.00 % ⁇ -2.9 CCY-3-O2 8.00 % 3.8 CLY-3-O2 8.00 % 6.7 CLY-3-O3 7.00 % ⁇ 1 82 mPa.s CLY-4-O2 5.00 % K 1 15.4 CPY-3-O2 5.00 % K 3 15.7 PY-2-3 2.00 % K 3 /K 1 1.02 Y-4O-O4 4.00 % V 0 2.47 V CCP-2F.F.F 3.00 %
  • the LC mixture N2 contains 3% of the compound CCP-2F.F.F of formula C
  • Example 3 The nematic LC mixture N3 is formulated as follows B(S)-2O-O4 3.00 % cl.p. 81.9°C B(S)-2O-O5 4.00 % ⁇ n 0.0926 B(S)-2O-O6 2.00 % n e 1.5737 CC-3-V 43.00 % n o 1.4811 CC-3-V1 1.50 % ⁇ -2.8 CCY-3-O2 8.50 % 4.3 CLY-3-O2 8.00 % 7.1 CLY-3-O3 7.50 % ⁇ 1 86 mPa.s CLY-4-O2 5.00 % K 1 15.0 CPY-3-O2 5.50 % K 3 15.0 PY-2-3 1.00 % K 3 /K 1 1.00 Y-4O-O4 5.00 % V 0 2.45 V CCP-2F.F.F 6.00 %
  • the LC mixture N3 contains 6% of the compound CCP-2F.F.F of formula C and
  • Example 4 The nematic LC mixture N4 is formulated as follows B(S)-2O-O5 4.00 % cl.p. 91.1°C CC-3-V 34.00 % ⁇ n 0.0903 CC-3-V1 7.50 % n e 1.5689 CCY-3-O1 4.50 % n o 1.4786 CCY-3-O2 8.00 % ⁇ -3.3 CLY-2-O4 5.00 % 3.7 CLY-3-O2 9.00 % 7.0 CLY-3-O3 8.00 % CLY-4-O2 5.00 % CLY-5-O2 5.00 % PYP-2-3 2.00 % Y-4O-O4 6.00 % CCP-2F.F.F 2.00 %
  • Example 5 The nematic LC mixture N5 is formulated as follows B(S)-5cy1O-O2 3.00 % cl.p.
  • Example 10 To the nematic mixture N1 of Example 1 are added 150 ppm of the stabiliser S1-1.
  • Example 11 To the nematic mixture N4 of Example 4 are added 300 ppm of the stabiliser S1-1, 100 ppm of the stabiliser S3-1 and 100 ppm of the stabiliser S3-3.
  • Example 12 To the nematic mixture N4 of Example 4 are added 300 ppm of the stabiliser S1-1, 50 ppm of the stabiliser S3-1 and 100 ppm of the stabiliser S3-3.
  • Example 13 To the nematic mixture N1 of Example 1 are added 150 ppm of the stabiliser S1-1 and 0.3% of the compound RM-1.
  • Example 14 To the nematic mixture N1 of Example 1 are added 150 ppm of the stabiliser S2-1 and 0.3% of the compound RM-35.
  • Example 15 To the nematic mixture N2 of Example 2 are added 200 ppm of the stabiliser S3-1 and 0.3% of the compound RM-64.
  • Example 16 To the nematic mixture N4 of Example 4 are added 200 ppm of the stabiliser S1-1 and 0.3% of the compound RM-120.
  • Example 17 To the nematic mixture N4 of Example 4 are added 200 ppm of the stabiliser S2-1 and 0.3% of the compound RM-171.
  • Example 18 To the nematic mixture N1 of Example 1 are added 150 ppm of the stabiliser S1-1, 0.3% of the compound RM-1 and 0.3% of the compound RM-171.
  • Example 19 To the nematic mixture N4 of Example 4 are added 150 ppm of the stabiliser S1-1 and 0.3% of the compound RM-1 and 0.2% of the compound RM-143.
  • Example 20 To the nematic mixture N4 of Example 4 are added 150 ppm of the stabiliser S2-1, 0.3% of the compound RM-1 and 0.1% of the compound RM-143.

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Abstract

L'invention concerne un milieu cristallin liquide à anisotropie diélectrique négative et son utilisation pour un affichage à matrice active, en particulier basé sur l'effet VA, SA-VA, IPS, PS-IPS, FFS, PS-FFS, UB-FFS ou PS-UB-FFS.
PCT/EP2022/076623 2021-09-28 2022-09-26 Milieu à cristaux liquides WO2023052283A1 (fr)

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