WO2009115186A1 - Milieu cristal liquide - Google Patents

Milieu cristal liquide Download PDF

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Publication number
WO2009115186A1
WO2009115186A1 PCT/EP2009/001515 EP2009001515W WO2009115186A1 WO 2009115186 A1 WO2009115186 A1 WO 2009115186A1 EP 2009001515 W EP2009001515 W EP 2009001515W WO 2009115186 A1 WO2009115186 A1 WO 2009115186A1
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Prior art keywords
compounds
independently
formula
formulas
alkyl
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PCT/EP2009/001515
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German (de)
English (en)
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WO2009115186A8 (fr
Inventor
Georg Bernatz
Melanie Klasen-Memmer
Matthias Bremer
Sabine Schoen
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Merck Patent Gmbh
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Priority to JP2011500063A priority Critical patent/JP5566995B2/ja
Publication of WO2009115186A1 publication Critical patent/WO2009115186A1/fr
Publication of WO2009115186A8 publication Critical patent/WO2009115186A8/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—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
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition

Definitions

  • the present invention relates to liquid crystal media and their use in liquid crystal displays, as well as these liquid crystal displays, especially liquid crystal displays, which use the ECB (Electrically Controlled
  • the liquid-crystal media according to the invention are distinguished by a particularly low switching time in the displays according to the invention with a simultaneously high voltage holding ratio.
  • Ads using the ECB effect have been referred to as VAN (Vertically Aligned Nematic) ads alongside IPS Qn Plane Switching) displays (eg: Yeo, SD, Lecture 15.3: "A LC Display for the TV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 758 & 759) and the long known TN (Twisted Nematic) displays, being established as one of the three most important recent types of liquid crystal displays, especially for television applications.
  • VAN Very Aligned Nematic
  • IPS Qn Plane Switching eg: Yeo, SD, Lecture 15.3: "A LC Display for the TV Application", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book II, pp. 758 & 759
  • TN Transmission Nematic
  • MVA Multi-Domain Vertical Alignment, eg: Yoshide, H. et al., Lecture 3.1: “MVA LCD for Notebooks or Mobile PCs ", SID 2004 International Symposium, Digest of Technical Papers, XXXV, Book I, pp. 6-9 and Liu, CT et al., Lecture 15.1: "A 46-inch TFT-LCD HDTV Technology ", SID 2004 International Symposium, Digest of Technical Papers , XXXV, Book II, pp.
  • ECB displays use liquid-crystalline media with negative dielectric anisotropy ( ⁇ )
  • TN and hitherto all common IPS displays use liquid-crystalline media with positive dielectric anisotropy.
  • liquid crystals are used as dielectrics whose optical properties reversibly change upon application of an electric voltage.
  • liquid crystal media are used, which are usually composed predominantly of liquid crystal compounds, all of which have the same sign of dielectric anisotropy and the largest possible amount have the dielectric anisotropy.
  • liquid crystal media with negative dielectric anisotropy for ECB displays, predominantly compounds with negative dielectric anisotropy are used.
  • the liquid-crystal media used predominantly and mostly even consist largely of liquid-crystal compounds with negative dielectric anisotropy.
  • the media used according to the present application are typically at most significant amounts of dielectrically neutral liquid crystal compounds and usually only very small amounts of or no dielectrically positive compounds used, since generally the liquid crystal displays should have the lowest possible drive voltages.
  • liquid crystal media of the prior art with correspondingly low drive voltages have relatively low electrical resistances or a low voltage holding ratio and often result in undesirable "flicker” and / or insufficient transmission in the displays.
  • phase range must be sufficiently wide for the intended application.
  • the switching times of the liquid-crystal media in the displays must be improved, ie reduced. This is especially important for ads for TV or multi-media applications.
  • ⁇ i the rotational viscosity of the liquid-crystal media
  • liquid-crystal media which does not have the disadvantages of the prior art media, or at least to a much lesser extent.
  • liquid crystal displays can be realized which have a short switching time in ECB displays and at the same time have a sufficiently broad nematic phase, a favorable birefringence ( ⁇ n) and a high voltage holding ratio.
  • Such media are especially for electro-optical displays with a
  • the medium according to the invention preferably has a negative dielectric anisotropy.
  • FK phases are needed, which must meet a variety of requirements. Particularly important here are the chemical resistance to moisture, air and physical influences such as heat, radiation in the infrared, visible and ultraviolet range and electrical alternating and alternating fields. Furthermore, technically usable LC phases require a liquid-crystalline mesophase in a suitable temperature range and a low viscosity.
  • Matrix liquid crystal displays are known.
  • active elements i.e., transistors
  • TFT thin-film transistors
  • TFTs made of compound semiconductors, such as e.g. CdSe or TFTs based on polycrystalline and u.a. amorphous silicon.
  • CdSe compound semiconductors
  • TFTs based on polycrystalline and u.a. amorphous silicon The latter technology currently has the greatest commercial significance worldwide.
  • the TFT matrix is applied on the inside of one glass plate of the display, while the other glass plate on the inside carries the transparent counterelectrode. Compared to the size of the pixel electrode, the TFT is very small and practically does not disturb the image.
  • This technology can also be extended for fully color-capable image representations, wherein a mosaic of red, green and blue filters is arranged in such a way that one filter element each lies opposite a switchable image element.
  • TFT displays commonly use crossed polarity in transmission and are backlit.
  • IPS cells or ECB (or VAN) cells are used, whereas for monitors, mostly IPS cells or TNB cells are used.
  • Cells and for notebooks, lap tops and for mobile applications mostly TN cells.
  • Such MFK displays are particularly suitable for TV applications, monitors and "note books” or for displays with high information density, for example in the automobile or aircraft industry.
  • MFK displays are particularly suitable for TV applications, monitors and "note books” or for displays with high information density, for example in the automobile or aircraft industry.
  • the disadvantage of the previously known MFK displays is based on their comparatively low contrast, the relatively high viewing angle dependency and the difficulty in generating gray levels in these displays, as well as their insufficient voltage holding ratio and their insufficient life span.
  • the invention has for its object MFK displays, not only for monitor and TV applications, but also for mobile phones and navigation systems, which are based on the ECB or on the IPS effect to provide the above-mentioned disadvantages or only to a lesser extent and at the same time have very high resistivities.
  • MFK displays not only for monitor and TV applications, but also for mobile phones and navigation systems, which are based on the ECB or on the IPS effect to provide the above-mentioned disadvantages or only to a lesser extent and at the same time have very high resistivities.
  • mobile phones and navigation systems which are based on the ECB or on the IPS effect to provide the above-mentioned disadvantages or only to a lesser extent and at the same time have very high resistivities.
  • the invention thus relates to a liquid-crystalline medium based on a mixture of polar compounds which contains at least one compound of the formula I and at least one compound of the formula II.
  • the mixtures according to the invention exhibit very broad nematic phase ranges with clearing points> 85 0 C, very favorable values for the capacitive threshold, relatively high values for the holding ratio and at the same time very good low-temperature stabilities at -30 0 C and -40 0 C as well as very low rotational viscosities. Furthermore, the mixtures according to the invention are distinguished by a good ratio of clearing point and rotational viscosity and by a high negative dielectric anisotropy.
  • the invention relates to a dielectric negative, nematic medium which
  • component A a first dielectric negative component (component A), which preferably consists of one or more compounds of the formula I.
  • R 11 and R 12 are each independently of one another H 1 is an unsubstituted alkyl or alkenyl radical having up to 15 C atoms, wherein in these radicals also one or more CH 2 groups
  • n and n are each independently 0 or 1 and (m + n) preferably 0 or 1, particularly preferably 0,
  • component B which consists of one or more compounds of formula II
  • -CO-O- or -O-CO- can be replaced so that O atoms are not directly linked to each other, preferably an unsubstituted alkyl, alkenyl, alkoxy or alkenyloxy, particularly preferably one of R 21 and R 22 a Alkyl or alkenyl radical and the other an alkyl, alkenyl, alkoxy or Alkenyloxyrest, preferably independently of one another alkyl having 1 to 7 C-atoms, preferably n-alkyl, particularly preferably n-alkyl having 1 to 5 C-atoms, alkoxy with 1 to 7 C atoms, preferably n-alkoxy, particularly preferably n-alkoxy having 1 to 5 C atoms or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms, preferably having 2 to 4 C atoms, preferably alkenyl in which one or more H atoms in all groups can be replaced by halogen atoms,
  • I and o are each independently O or 1 and
  • component C a dielectrically neutral component consisting of one or more compounds of formula III
  • R 31 and R 32 each independently of one another have one of the meaning given for R 11 and R 12 and preferably alkyl having 1 to 7 C atoms, preferably n-alkyl, particularly preferably n-alkyl having 1 to 5 C atoms, alkoxy with 1 to 7 C atoms, preferably / 7-alkoxy, particularly preferably n-alkoxy having 2 to 5 C atoms, alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms, preferably having 2 to 4 C atoms, preferably alkenyloxy,
  • p and q are each independently, 0 or 1
  • component D a further dielectrically negative component which consists of one or more compounds selected from the group of the compounds of the formulas IV and V.
  • R R, -, 51 and R •, 52 are each independently one of R 21
  • R and R 22 have given meaning and preferably alkyl having 1 to 7 carbon atoms, preferably n-alkyl and particularly preferably n-alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 7 carbon atoms, preferably n-alkoxy and particularly preferably n-alkoxy having 2 to 5 C atoms or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms, preferably having 2 to 4 C atoms, preferably alkenyloxy,
  • each of r and s independently of one another is O or 1
  • component E a chiral component consisting of one or more chiral compounds
  • the media of the invention are dielectrically negative.
  • the medium according to the invention preferably contains one, two, three, four or more, preferably one, two or three or more, compounds of the formula I.
  • R 11 and / or R 12 are H, alkyl, alkenyl or alkoxy, preferably with up to 6 CC - AAttoommeenn ,, R 12 very particularly preferably alkoxy or alkenyloxy,
  • R 11 and R 12 are both alkyl, where the alkyl radical may be the same or different,
  • R 11 is straight-chain alkyl, vinyl, 1-alkenyl or 3-alkenyl.
  • the compounds of the formula I are preferably selected from the group of the compounds of the formulas 1-1 to I-4, preferably from the group of the formulas 1-1 and I-3, particularly preferably of the formula 1-1,
  • R 11 is preferably alkyl having 1 to 7, preferably having 1 to 5, carbon atoms, preferably n-alkyl and R 12 is preferably alkoxy having 1 to 5, preferably 2 to 4, C - atoms mean.
  • the compounds of the formula II are preferably selected from the group of the compounds of the formulas 11-1 and II-2, preferably of the formula II-2,
  • R 21 is alkyl or alkenyl
  • R 22 is alkyl, alkenyl, alkoxy or alkenyloxy
  • R> 21 has the meaning given above and is preferably alkyl having 1 to 7, preferably having 1 to 5, carbon atoms, preferably n-alkyl.
  • the medium contains one or more compounds of the formula III in which at least two of the rings
  • the medium contains one or more compounds of the formula III from the group of the compounds of the formulas III-1 to III-II, preferably selected from the group of the compounds of the formulas III-III to III-9, preferably from Group III-1 to III-6 and more preferably from group III-1 and III-4,
  • Y 3 is H or F and preferably
  • R is alkyl or alkenyl
  • R 32 is alkyl, alkenyl or alkoxy, preferably alkyl or
  • Alkenyl particularly preferably alkenyl.
  • the medium particularly preferably contains one or more compound (s) of the formula UM selected from the group of the formulas UMc, in particular preferably of the formula HM in the R 31 vinyl or 1-propenyl and R 32 alkyl, preferably / i-alkyl, in particular preferably R 31 is vinyl and R 32 is propyl and of the formulas HMd, in particular preferably of the formula IH-1 in the R 31 and R 32 are independently vinyl or 1-propenyl, and R 31 is vinyl and
  • R and R are vinyl.
  • the medium contains one or more compounds of the formula III-1 selected from the group of the compounds of the formulas HMa to HMe
  • Alkenyl and alkenyl 'independently, alkenyl having 2 to 7 carbon atoms, preferably having 2 to 5 carbon atoms.
  • the medium according to the invention particularly preferably contains compounds of the formula III-1 in amounts of 20% by weight or more, in particular of 25% by weight or more, very particularly preferably of 30% by weight or more, in particular compounds of the formula MMc '
  • the medium contains one or more compounds of the formula III-1 selected from the group of the compounds of the formulas III-1a and III-1b, preferably of the formulas IIIa and / or III-1b preferably of the formula II-Ia.
  • the medium in this embodiment contains no compounds of formula III, preferably the
  • Formula 111-1 with one alkenyl end group or more alkenyl end groups, so preferably no compounds of the formulas IM-Ic to IH-Ie.
  • the medium in this embodiment particularly preferably contains one or more compounds selected from the group of the compounds of the formulas CC-2-3, CC-2-5, CC-3-4 and CC-3-5, the acronyms (abbreviations) in Tables A to C and illustrated in Table D by Examples.
  • the medium contains one or more compounds of the formula MI-2 selected from the group of the compounds of the formulas III-2a to III-2d, preferably of the formulas II-2a and / or III-2b, more preferably of the formula Formula III-2b,
  • the medium contains one or more compounds of the formula III-3 selected from the group of the compounds of the formulas III-3a to III-3c
  • Alkyl and alkyl 'independently of one another are alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, alkenyl alkenyl having 2 to 7 C atoms, preferably 2 to 5
  • C atoms mean.
  • the proportion of these biphenyls in the total mixture is preferably 3 wt .-% or more, in particular 5 wt .-% or more.
  • Preferred compounds of the formulas III-3a or III-3b are the
  • Particularly preferred compounds of formula III-3b are the compounds of the following formula
  • the medium contains one or more compounds of the formula III-4, particularly preferably one or more compound (s) in which R 31 is vinyl or 1-propenyl and R 32 is alkyl, preferably n-alkyl, particularly preferably R 31 Vinyl and
  • the medium contains one or more compounds of the formula III-4 selected from the group of the compounds of the formulas III-4a to III-4d, preferably of the formulas III-4a and / or III-4b, more preferably the Formula III-4b,
  • Alkyl and alkyl 'independently of one another are alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms, alkoxyalkoxy having up to 1 to 5 C atoms, preferably 2 to
  • the medium contains one or more compounds of the formula III-5, in particular preferably one or more compound (s) in which R 31 is alkyl, vinyl or 1-
  • the medium contains one or more compounds of the formula III-5 selected from the group of the compounds of the formulas III-5a to III-5d, preferably of the formulas III-5a and / or III-5b, particularly preferably of the formula III-5a
  • Alkoxy alkoxy having up to 1 to 5 carbon atoms, preferably having 2 to 4 carbon atoms and
  • Alkoxy alkoxy having up to 1 to 5 carbon atoms, preferably having 2 to 4 carbon atoms and
  • the medium contains one or more compounds of the formula III-6 selected from the group of the compounds of the formulas III-6a to III-6c, preferably of the formulas III-6a and / or III-6b, particularly preferably of the formula lll-6a
  • the media according to the invention particularly preferably contain one or more compounds selected from the compounds of the formulas III-6a, preferably selected from the group of the compounds PGP-2-3, PGP-3-3 and PGP-3-4, and of the formula III. 6b, preferably selected from the group of the formulas PGP-1-2V, PGP-2-2V and PGP-3-2V, the acronyms (abbreviations) being illustrated in Tables A to C and illustrated in Table D by examples.
  • the medium contains one or more compounds of formula III-10 selected from the group of compounds of formulas IM-IOa and IM-IOb wherein
  • Alkyl and alkyl 'independently of one another are alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms.
  • the medium contains one or more compounds of the formula III-1 1 of the compounds of the formulas III-11a
  • Alkyl and alkyl 'independently of one another are alkyl having 1 to 7 C atoms, preferably having 2 to 5 C atoms.
  • the medium contains one or more compounds of the formula IV selected from the group of the compounds of the formulas IVA to IVD, preferably IVA to IVC and very particularly preferably IVA and IVB
  • Alkyl or alkoxy more preferably (O) C v H 2 v + i,
  • Z 21 and Z 22 are independently a single bond
  • -CH 2 -CH 2 -, -CH CH-, -CH 2 O-, -OCH 2 -, -O-, -CH 2 -, -CF 2 O-, or -OCF 2 -, preferably a single bond or -CH 2 CH 2 -, more preferably a single bond,
  • the medium contains one or more compounds of the formula IV selected from the group of the compounds of the formulas IV-1 to IV-14
  • Y 4 1 to Y 4 6 independently of one another H or F
  • X 4 1 and X 4 2 are both H or one of X 4 1 and X 4 2 H and the other F,
  • R 41 is alkyl or alkenyl and R 42 is alkyl, alkenyl, alkoxy or alkenyloxy, preferably (O) C v H 2v + i and
  • V is an integer from 1 to 6.
  • the medium contains one or more compounds of the formula IV-1 selected from the group of the compounds of the formulas IV-Ia to IV-Id, preferably of the formulas IV-I b and / or IV-Id, particularly preferably of the formula IV-I b,
  • Preferred compounds of the formulas IV-Ic or IV-Id are the compounds of the following formulas
  • R 4 1 has the respective meaning given above in formula IV.
  • the medium contains one or more compounds of the formula IV-3 selected from the group of the compounds of the formulas IV-3a to IV-3d, preferably of the formulas IV-3b and / or IV-3d, more preferably of the formula IV-3b,
  • the concentration of these biphenyl compounds in the total mixture is 3% by weight or more, more preferably 5% by weight or more, and most preferably from 5 to 25% by weight.
  • the medium contains one or more compounds of the formula IV-4 selected from the group of the compounds of the formulas IV-4a to IV-4d, preferably of the formulas IV-4a and / or IV-4b, more preferably the Formula IV-4b,
  • Preferred compounds of the formulas IV-4c or IV-4d are the compounds of the following formulas
  • the medium contains one or more compounds of the formula IV-4 of the following sub-formula IV-4e
  • R 41 has the meaning given above and
  • n and z are each independently an integer from 1 to 6 and
  • n + z is preferably an integer from 1 to 6.
  • the medium comprises one or more compounds of the formula IV-5 selected from the group of the compounds of the formulas IV-5a to IV-5d, preferably of the formulas IV-5b and / or IV-5d,
  • Preferred compounds of the formulas IV-5c or IV-5d are the compounds of the following formulas
  • the medium contains one or more compounds of the formula I-4 selected from among Group of the compounds of the formulas IV-6a to IV-6d, preferably of the formulas IV-6a and / or IV-6c, particularly preferably of the formula IV-6a,
  • R has the meaning given above for R i41 and
  • n 1 to 6.
  • R is preferably straight-chain alkyl or alkoxy having in each case 1 to 6 C atoms or alkylalkoxy, alkenyl or alkenyloxy having 2-6 C atoms, particularly preferably alkyl having 1-5 C atoms, preferably methyl, ethyl, propyl, butyl, or furthermore alkoxy having 1-5 C atoms, preferably hexyl, methoxy, ethoxy, propoxy, or butoxy.
  • the medium contains one or more compounds of the formula IV-7 selected from the group of the compounds of the formulas IV-7a to IV-7d, preferably of the formulas IV-7a and / or IV-7c, more preferably the Formula IV-7a,
  • Alkoxy alkoxy having up to 1 to 5 carbon atoms, preferably having 2 to 4 carbon atoms and
  • R has the meaning given above for R, 41 and
  • n 1 to 6.
  • R is preferably straight-chain alkyl or alkoxy having in each case 1 to 6 C atoms or alkylalkoxy, alkenyl or alkenyloxy having 2-6 C atoms, particularly preferably alkyl having 1-5 C atoms, preferably methyl, ethyl, propyl, butyl, or furthermore alkoxy having 1-5 C atoms, preferably hexyl, methoxy, ethoxy, propoxy, or butoxy.
  • the medium contains one or more compounds of the formula IV-8 selected from the group of the compounds of the formulas IV-8a and IV-8b, particularly preferably IV-8b
  • the medium contains one or more compounds of the formula IV-9 selected from the group of the compounds of the formulas IV-9a to IV-9d IV-9a
  • v is an integer from 1 to 6.
  • the medium contains one or more compounds of the formula IV-10 selected from the group of the compounds of the formulas IV-IOa to IV-IOe
  • v is an integer from 1 to 6.
  • the medium contains one or more compounds of the formula IV-11 selected from the group of the compounds of the formulas IV-11a and IV-11b, particularly preferably IV-11b
  • the medium contains one or more compounds of the formula IV-14 selected from the group of the compounds of the formulas IV-14a to IV-14d, preferably of the formulas IV-14a and / or IV-14b, more preferably of the formula Formula IV-14b,
  • the medium (additionally) preferably contains one or more compounds of the formula V. selected from the group of the compounds of the formulas V-1 to V-8, preferably of the formulas V-7 and / or V-8
  • R 51 alkyl or alkenyl
  • R 52 is alkyl, alkenyl, alkoxy or alkenyloxy
  • the medium may consist essentially of compounds of the formulas I, II, III and V.
  • the medium additionally contains one or more compounds which have a fluorinated phenanthrene unit, preferably compounds of the formula V, preferably selected from the group of the compounds of the formulas V-9 and V-10
  • R 51 is alkyl or alkenyl
  • R 52 is alkyl, alkenyl, alkoxy or alkenyloxy.
  • the medium additionally contains one or more compounds which have a fluorinated dibenzofuran unit, preferably compounds of the formula V, preferably of the formula V-11
  • R 51 is alkyl or alkenyl
  • R 52 is alkyl, alkenyl, alkoxy or alkenyloxy.
  • component E of the liquid crystal media according to the present invention are selected from the known chiral dopants.
  • Component E preferably predominantly, more preferably substantially and very particularly preferably almost completely, consists of one or more compounds selected from the group of the compounds of the following formulas VI to VIII
  • R 61 and R 62 , R 71 to R 73 and R 8 are each independently of one another, have the meaning given above in formula II for R, and alternatively H, CN, F, Cl CF 3 , OCF 3 , CF 2 H or OCF 2 H and at least one of R 61 and R 62 is a chiral group,
  • u and v, and x, y and z are each independently 0 or 1, preferably
  • x and v are both 1, mean.
  • Particularly preferred embodiments of the present invention fulfill one or more of the following conditions.
  • the liquid crystalline medium has a birefringence of 0.095 or more.
  • the liquid-crystalline medium contains one or more
  • Formula I ranges from 1 to 20%, preferably from 2 to 15% and most preferably from 3 to 10%. iv.
  • the proportion of compounds of the formula II in the total mixture is 10% by weight or more.
  • the concentrations of the individual homologous compounds of the formula II are in the range from 2 to 15%, preferably from 3 to 12% and particularly preferably from 4 to 10%.
  • the proportion of compounds of the formula III in the overall mixture is 10% or more, preferably 70% or less and particularly preferably 20% by weight or more.
  • the liquid-crystalline medium contains one or more particularly preferred compounds of the formulas III-1c and III-1 d selected from the following partial formulas:
  • alkyl has the meaning given above and preferably, in each case independently of one another alkyl having 1 to 6, preferably having 2 to 5 carbon atoms and particularly preferably n-alkyl.
  • the liquid-crystalline medium contains one or more
  • R 31 and R 32 have the abovementioned meaning and preferably R 31 and R 32 are each independently a straight-chain alkyl, alkoxy or alkenyl radical having 1 or 2 to 7 C atoms, particularly preferably straight-chain alkyl, furthermore alkenyl mean.
  • the proportion of these compounds in the mixture is preferably 5 to 40 wt .-%. ix.
  • the liquid-crystalline medium contains one or more
  • CC-nV and / or CC-n-Vm eg, preferably CC-5-V, preferably in a concentration of up to 25% or less, CC-3-V, preferably in a concentration of up to
  • CC-nm and / or CC-n-Om eg: preferably CC-3-2 and / or CC-3-3 and / or CC-3-4 and / or CC-3-O2 and / or CCP-5-O2
  • CP-nm and / or CP-n-Om eg: preferably CP-3-2 and / or CP-5-2 and / or CP-3-O1 and / or CP-3-O2
  • PP-n- Vm eg: preferably PP-n-2V
  • PP-n-IVm eg: preferably PP-n-2V1
  • CCP-n-m eg preferably CCP-n-1
  • CGP-nm and CCOC-nm wherein the meaning of the Akonyme (abbreviations) are illustrated in Tables A to C and illustrated in Table D by examples, preferably in a total concentration of up to 10% or more to 70% or less.
  • the liquid-crystalline medium consists essentially of
  • the liquid-crystalline medium contains one or more compounds of the formula I with four six-membered or ten-membered rings or ring systems in amounts of 1 wt .-% to 15 wt .-%, in particular from 2 wt .-% to 12 wt .-%, and most preferably from 3 to 8 wt .-% per single compound.
  • the liquid-crystalline medium contains one or more
  • Compounds of formula IV preferably in amounts of 2 wt .-% or more, in particular of 5 wt .-% or more, and most preferably from 5 wt .-% or more to 25 wt .-% or less, in particular in the range from 2% by weight or more to 12% by weight or less per homologous single compound.
  • the liquid-crystalline medium contains one or more
  • Compounds of the formula IV-1 to IV-3 preferably IV-1 and / or IV-3, preferably of the formulas IV-Ib and / or IV-Id and / or IV-3b and / or IV-3d, more preferably IV -I b and / or IV-3b, preferably in a total concentration of 60% or less and in a concentration of 2 wt .-% or more, in particular of 5 wt .-% or more, and most preferably of 5 wt. -% or more to 20 wt .-% or less per homologous individual compound.
  • the liquid-crystalline medium contains one or more
  • the liquid-crystalline medium contains one or more
  • Compounds of formula IV-6 and / or IV-7 preferably of formulas IV-6a and / or IV-7a, preferably in a total concentration of 50% or less and preferably in a concentration of 2% by weight or more to 10 Wt .-% or less per homologous single compound of formula IV-6 and in a concentration of 2 % By weight or more to 20% by weight or less per homologous single compound of formula IV-6.
  • the liquid-crystalline medium preferably contains one or more compounds of the formula IV in amounts of 2% by weight or more, in particular of 5% by weight or more, and very particularly preferably of 5% by weight to 25% by weight in particular in the range of 2% to 12% by weight per single compound.
  • the liquid-crystalline medium contains one or more
  • Compounds of formula V preferably in amounts of 3 wt .-% or more, in particular of 5 wt .-% or more, and most preferably from 5 wt .-% to 25 wt .-%, in particular in the range of 2 wt. -% to 20 wt .-% per single compound.
  • Another object of the invention is an electro-optical display with an active matrix addressing based on the ECB effect, characterized in that it contains as a dielectric liquid-crystalline medium according to the present invention.
  • the liquid crystal mixture on a nematic phase range of at least 60 degrees and a flow viscosity V 2 O of at most 30 mm 2 • s "1 at 20 0 C.
  • the liquid-crystal mixture according to the invention has a ⁇ of about -0.5 to -8.0, in particular of about -2.5 to -6.0, where ⁇ denotes the dielectric anisotropy.
  • the rotational viscosity ⁇ i is preferably 200 mPa ⁇ s or less, more preferably 170 mPa ⁇ s or less.
  • the birefringence ⁇ n in the liquid-crystal mixture is usually between 0.06 and 0.16, preferably between 0.08 and 0.12.
  • the mixtures according to the invention are suitable for all VA TFT applications, such as, for example, VAN, MVA, (S) -PVA and ASV. Furthermore, they are suitable for IPS Qn pjane switching), FFS (fringe field switching) and PALC applications with negative ⁇ .
  • the nematic liquid-crystal mixtures in the displays according to the invention generally contain two components A and B, which in turn consist of one or more individual compounds.
  • one (or more) individual compound (s) is preferably selected which have a value of ⁇ ⁇ -0.8. This value must be the more negative the smaller the proportion A of the total mixture is.
  • one (or more) individual compound (s) is preferably selected which have a value of ⁇ ⁇ -0.8. This value must be the more negative, the smaller the proportion B of the total mixture.
  • the component C has a pronounced nematogeneity and a flow viscosity of not more than 30 mm 2 • s "1 , preferably not more than 25 mm 2 s at 20 ° C.
  • Particularly preferred individual compounds of component C are extremely low-viscosity nematic liquid crystals having a flow viscosity of not more than 18, preferably not more than 12 mm 2 • s -1 , at 20 ° C.
  • Component C is monotropic or enantiotropic nematic and can be found in
  • Liquid crystal mixtures prevent the occurrence of smectic phases up to very low temperatures. If, for example, a smectic liquid-crystal mixture is mixed with in each case different materials with high nematogeneity, the degree of suppression of smectic phases achieved can be used to compare the nematogeneity of these materials.
  • these liquid crystal phases may also contain more than 18 components, preferably 18 to 25 components.
  • the phases contain 4 to 15, in particular 5 to 12, and particularly preferably 10 or less, compounds of the formulas I and II and / or III and / or IV and / or V.
  • other ingredients may be present, for. B. in an amount of up to 45% of the total mixture, but preferably up to 35%, in particular up to 10%.
  • the other constituents are preferably selected from the nematic or nematogenic substances, in particular the known substances, from the classes of the azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, cyclohexane-carboxylic acid phenyl or cyclohexyl esters, phenylcyclohexanes, cyclohexyl biphenyls, cyclohexylcyclohexanes, cyclohexylnaphthalenes, 1,4-biscyclohexylbiphenyls or cyclohexylpyrimidines, phenyl- or cyclohexyldioxanes, optionally halogenated stilbenes, benzylphenyl ethers, tolans and substituted cinnamic acid esters.
  • L and E are each a carbo- or heterocyclic ring system of the 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted biphenyl, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted pyrimidine and 1,3 Dioxane rings, 2,6-disubstituted naphthalene, di- and tetrahydronaphthalene, quinazoline and tetrahydroquinazoline,
  • Q is halogen, preferably chlorine, or -CN
  • R 91 and R 92 are each alkyl, alkenyl, alkoxy, alkanoyloxy or alkoxycarbonyloxy having up to 18, preferably up to 8 carbon atoms, or one of these radicals also CN, NC, NO 2 , NCS, CF 3 , OCF 3 , F, Cl or Br.
  • R 91 and R 92 are different from each other, one of these radicals usually being an alkyl or alkoxy group.
  • Other variants of the proposed substituents are in use. Many such substances or mixtures thereof are commercially available. All these substances can be prepared by literature methods.
  • the concentration of the compounds of formula IX in the total mixture is preferably 1% to 25%, more preferably 1 to 15% and most preferably 2% to 9%.
  • the media of the invention may also contain a dielectrically positive component whose total concentration is preferably 10% by weight or less based on the total medium.
  • liquid-crystal media according to the invention contain in total, based on the total mixture
  • Concentrations of the respective different components can be combined with each other, however, the total concentration of all compounds, and all components does not exceed 100%.
  • the liquid-crystal media according to the invention comprise components A and C and preferably one or more components selected from the group of components B, D and E, preferably predominantly, more preferably substantially and very preferably almost completely, of said components ,
  • the liquid crystal media according to the invention preferably have a nematic phase of at least from -20 0 C or less up to 70 0 C or more, particularly preferably of -30 ° C or less to 80 0 C or more, very particularly preferably from -40 0 C or less to 85 ° C or more, and even most preferably at from -40 0 C or less to 90 ° C or more.
  • the term "having a nematic phase” means that no smectic phase and no crystallization are observed at low temperatures at the corresponding temperature and, on the other hand, that no clarification occurs during heating from the nematic phase a fluid viscosity viscometer at the appropriate temperature and checked by storage in test cells of a corresponding electro-optic layer thickness for at least 100 hours.
  • the storage stability at a temperature of -20 0 C in a corresponding test cell is 1,000 h or more
  • the medium is at At temperatures of -30 0 C and -40 0 C
  • the respective times are 500 h and 250 h, respectively high temperatures
  • the clearing point is measured in capillaries by conventional methods.
  • the liquid-crystal media according to the invention are characterized by values of the optical anisotropies in the middle to low range.
  • the values of the birefringence are preferably in the range of 0.065 or more to 0.130 or less, more preferably in the range of 0.080 or more to 0.120 or less and most preferably in the range of 0.085 or more to 0.110 or less.
  • the liquid crystal media of the invention have a negative dielectric anisotropy and have relatively high values of the amount of dielectric anisotropy (I ⁇ l), preferably in the range of 2.7 or more to 5.3 or less, preferably to 4.5 or less, preferably from 2.9 or more to 4.5 or less, more preferably from 3.0 or more to 4.0 or less, and most preferably from 3.5 or more to 3.9 or less.
  • I ⁇ l the amount of dielectric anisotropy
  • the liquid-crystal media according to the invention have relatively small values for the threshold voltage (V 0 ) in the range of 1, 7 V or more to 2.5 V or less, preferably from 1, 8 V or more to 2.4 V or less, more preferably from 1, 9 V or more to 2.3 V or less, and more preferably from 1.95 V or more to 2.1 V or less.
  • V 0 threshold voltage
  • the liquid-crystal media according to the invention have values of the amount of the dielectric anisotropy (I ⁇ l), which are preferably in the range from 1, 7 or more to 4.9 or less to 4.3 or less, preferably from 2.3 or more to
  • the liquid crystal media of the present invention have values for the threshold voltage (Vo) in the range of 1.9V or more to 2.5V or less, preferably 2.1V or more to 2.3V or less.
  • liquid-crystal media according to the invention have high values for the voltage holding ratio in liquid-crystal cells.
  • liquid-crystal media with a low drive voltage or threshold voltage have a lower voltage
  • the term "compounds”, also written as “compound (s)”, unless explicitly stated otherwise, means both one or more compounds.
  • the individual compounds are, unless stated otherwise, in the mixtures in concentrations generally from 1% or more to 30% or less, preferably from 2% or more to 30% or less, and more preferably from 3% or more to 16% or less used.
  • Constant the concentration of the constituents in the composition is preferably 5% or more, more preferably 10% or more, most preferably 20% or more,
  • the concentration of the constituents in the composition is preferably 50% or more, more preferably 55% or more and most preferably 60% or more,
  • the concentration of the constituents in the composition is preferably 80% or more, more preferably 90% or more and most preferably 95% or more and
  • the concentration of the constituents in question in the composition is preferably 98% or more, more preferably 99% or more and most preferably 100.0%.
  • the concentration of the compound in question is preferably 1% or more, more preferably 2% or more, most preferably 4% or more.
  • concentration of the compound in question is preferably 1% or more, more preferably 2% or more, most preferably 4% or more.
  • concentration of the compound in question is preferably 1% or more, more preferably 2% or more, most preferably 4% or more.
  • ⁇ means less than or equal to, preferably less than and ">" greater than or equal to, preferably greater.
  • dielectrically positive compounds mean those compounds having a ⁇ > 1.5, "dielectrically neutral compounds” those having -1, 5 ⁇ ⁇ 1, 5 and “dielectrically negative” compounds those having ⁇ ⁇ - 1, 5.
  • the dielectric anisotropy of the compounds is determined by dissolving 10% of the compounds in a liquid-crystalline host and determining the capacity of the resulting mixture in at least one test cell with 20 ⁇ m layer thickness with homeotropic and with homogeneous surface orientation at 1 kHz
  • the measurement voltage is typically 0.5 V to 1.0 V, but it is always lower than the capacitive threshold of the respective liquid-crystal mixture investigated.
  • the host mixture for dielectrically positive and dielectrically neutral compounds is ZLI-4792 and for dielectrically negative compounds
  • the liquid-crystal media according to the invention can also contain further additives, such as, for example, B. stabilizers and / or pleochroic Dyes and / or chiral dopants in the usual amounts.
  • the amount of these additives used is preferably 0% or more to 10% or less in total, based on the amount of the entire mixture, more preferably 0.1% or more to 6% or less.
  • the concentration of the individual compounds used is preferably 0.1% or more to 3% or less. The concentration of these and similar additives is usually not taken into account in the indication of the concentrations and the concentration ranges of the liquid crystal compounds in the liquid-crystal media.
  • the liquid-crystal media according to the invention contain a polymer precursor which contains one or more reactive compounds, preferably reactive mesogens and, if required, further additives such as, for example, B. polymerization initiators and / or polymerization moderators in the usual amounts.
  • the amount of these additives used is generally 0% or more to 10% or less based on the amount of the whole mixture, preferably 0.1% or more to 2% or less.
  • the concentration of these and similar additives is not taken into account in the indication of the concentrations and the concentration ranges of the liquid crystal compounds in the liquid-crystal media.
  • compositions consist of several compounds, preferably from 3 or more to 30 or less, more preferably from 6 or more to 20 or less and most preferably from 10 or more to 16 or fewer compounds which are mixed in a conventional manner.
  • the desired amount of the minor components is dissolved in the components that make up the main ingredient of the mixture. This is conveniently carried out at elevated temperature. If the selected temperature is above the clearing point of the main constituent, the completion of the dissolution process is particularly easy to observe.
  • the liquid crystal mixtures in other conventional ways, for. B. using premixes or from a so-called "multi-bottle system" produce.
  • the mixtures according to the invention exhibit very broad nematic phase ranges with clearing points 65 ° C or more, very favorable values for the capacitive threshold, relatively high values for the holding ratio and at the same time very good low-temperature stabilities at -30 0 C and -40 0 C. Furthermore, characterized the mixtures according to the invention by low rotational viscosities Y 1 from.
  • the media of this invention may also contain compounds wherein, for example, H, N, O, Cl, F are replaced by the corresponding isotopes are.
  • the structure of the liquid crystal displays according to the invention corresponds to the usual geometry, as z. As described in EP-OS 0 240 379.
  • liquid crystal phases according to the invention can be modified such that they can be used in any type of z.
  • B. ECB, VAN, IPS, GH or ASM-VA LCD display can be used.
  • Stabilizers which may be added, for example, to the mixtures according to the invention, preferably in amounts of from 0.01 to 6% by weight, in particular from 0.1 to 3% by weight, are mentioned below in Table F.
  • threshold voltage for the present invention refers to the capacitive threshold (V 0 ), also called Freedericksz threshold, unless explicitly stated otherwise.
  • the electro-optical properties eg. B. the threshold voltage (V 0 ) (capacitive measurement), as well as the switching behavior, determined in Merck Japan Ltd produced test cells.
  • the measuring cells have substrates of sodium glass (sodalime glass) and are in an ECB or VA configuration with polyimide orientation layers (SE-1211 with thinner ** 26 (mixing ratio 1: 1) both from Nissan Chemicals, Japan) which are perpendicular to each other are rubbed and that cause a homeotropic orientation of the liquid crystals carried out.
  • the area of the transparent, nearly square electrodes made of ITO is 1 cm 2 .
  • liquid crystal mixtures used are not mixed with a chiral dopant unless otherwise stated, but they are also particularly suitable for applications in which such a doping is required.
  • the Voltage Holding Ratio is determined in test cells manufactured at Merck Japan Ltd.
  • the measuring cells have substrates of sodium glass
  • the voltage used has a frequency of 60 Hz.
  • the rotational viscosity is determined by the method of the rotating permanent magnet and the flow viscosity in a modified Ubbelohde viscometer.
  • n and m are integers and the three dots are placeholders for other abbreviations in this table.
  • mixtures according to the invention preferably contain, in addition to the compounds of the formulas I, one or more compounds of the compounds mentioned below.
  • n, m and z are each independently an integer, preferably 1 to 6)
  • Table E lists chiral dopants which are preferably used in the mixtures according to the invention.
  • the media according to the invention comprise one or more compounds selected from the group of compounds of Table F. Mischun ⁇ sbeiitul
  • various of the mentioned example mixtures can be mixed with one another, with mixtures having similar, advantageous results being obtained.
  • the usually associated increase in the number of mixture components usually leads to an improvement in the storage stability of such mixtures, especially at low temperatures.

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Abstract

L'invention concerne un milieu cristal liquide, diélectriquement négatif, qui contient a) un premier composant diélectriquement négatif (composant A), qui est constitué d'un ou plusieurs composés diélectriquement négatifs de formule (I), et b) un deuxième composant diélectriquement négatif (composant B), qui est constitué d'un ou plusieurs composés diélectriquement négatifs de formule (II), les paramètres ayant les significations données dans la revendication 1. L'invention concerne également l'utilisation de ce milieu cristal liquide dans un affichage électro-optique, en particulier dans un affichage à matrice active se fondant sur l'effet VA, ECB, PALC, FFS ou IPS, ainsi que les affichages de ce type.
PCT/EP2009/001515 2008-03-17 2009-03-04 Milieu cristal liquide WO2009115186A1 (fr)

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JP5566995B2 (ja) 2014-08-06
DE102009011666A1 (de) 2009-09-24
TW200948936A (en) 2009-12-01
TWI504732B (zh) 2015-10-21
WO2009115186A8 (fr) 2010-10-21
JP2011517464A (ja) 2011-06-09
DE102009011666B4 (de) 2018-12-27

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