[go: up one dir, main page]

WO2012076121A1 - Milieu à cristaux liquides et écran à cristaux liquides - Google Patents

Milieu à cristaux liquides et écran à cristaux liquides Download PDF

Info

Publication number
WO2012076121A1
WO2012076121A1 PCT/EP2011/005889 EP2011005889W WO2012076121A1 WO 2012076121 A1 WO2012076121 A1 WO 2012076121A1 EP 2011005889 W EP2011005889 W EP 2011005889W WO 2012076121 A1 WO2012076121 A1 WO 2012076121A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
formula
independently
formulas
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2011/005889
Other languages
German (de)
English (en)
Other versions
WO2012076121A8 (fr
Inventor
Markus Czanta
Elvira Montenegro
Izumi Saito
Mark Goebel
Michael Junke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of WO2012076121A1 publication Critical patent/WO2012076121A1/fr
Publication of WO2012076121A8 publication Critical patent/WO2012076121A8/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C09K19/542—Macromolecular compounds
    • 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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458—Uncondensed pyrimidines
    • 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
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • 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
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3004—Cy-Cy
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09K19/08—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
    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3019—Cy-Cy-Ph-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3025—Cy-Ph-Ph-Ph

Definitions

  • the present invention relates to liquid crystalline media and liquid crystal displays containing these media, especially to displays addressed by an active matrix, and more particularly to Twisted Nematic (TN), In Plane Switching (IPS) or Fringe Field displays
  • LCDs Liquid crystal displays
  • LCDs are used in many areas to display information. LCDs are used for both direct-view and projection-type displays.
  • electro-optical modes for example Twisted Nematic (TN), Super Twisted Nematic (STN), Optically Compensated Bend (OCB) and Electrically Controlled Birefringence (ECB) are used along with their various modifications and others. All of these modes use an electric field that is substantially perpendicular to the substrates or to the liquid crystal layer.
  • electro-optical modes that use an electric field that is substantially parallel to the substrates or the liquid crystal layer, such as the jn-plane switching (IPS) mode (as in DE 40 00 451 and EP 0 588 568) and in Fringe Field Switching (FFS) mode, which has a strong "fringe field", a strong electric field near the edge of the electrodes, and an electric field throughout the cell, which has both a strong vertical component and an electric field
  • IPS jn-plane switching
  • FFS Fringe Field Switching
  • LCDs liquid crystals according to the present invention are preferably used in displays of this type.
  • liquid-crystalline media with eh he smaller values of dielectric anisotropy are used, but also in IPS displays partially liquid-crystalline media are used with a dielectric anisotropy of only about 3 or even lower.
  • These displays require new liquid-crystalline media with improved properties.
  • the response times for many types of applications need to be improved. Therefore, liquid-crystalline media with lower viscosities (.eta.), Especially with lower rotational viscosities (.gamma.), Are required.
  • the rotational viscosity should be 80 mPa.s or less, preferably 60 mPa.s or less and especially 55 mPa.s or more, especially for monitor applications
  • the media must have a range of nematic phase of appropriate width and position, as well as suitable birefringence (An)
  • dielectric anisotropy should be high enough to allow a reasonably low operating voltage.
  • ⁇ should be higher than 2 and very preferably higher than 3, but preferably not higher than 15 and in particular not higher than 12, since this would be contrary to an at least reasonably high specific resistance.
  • the rotational viscosity should preferably be 120 mPa ⁇ s or less, and more preferably 100 mPa ⁇ s or less.
  • the dielectric anisotropy ( ⁇ ) should preferably be higher than 8 and more preferably higher than 2.
  • the displays according to the present invention by an active matrix (active matrix LCDs, short AMDs), preferably by a matrix of thin-film transistors (TFTs), addressed.
  • active matrix LCDs active matrix LCDs, short AMDs
  • TFTs thin-film transistors
  • the liquid crystals according to the invention can also be advantageously used in displays with other known addressing agents. There are many different display modes that include composite systems of low molecular weight liquid crystal materials along with polymer use materials.
  • the modes particularly preferred according to the present invention employ the liquid crystal medium as such, oriented on surfaces. These surfaces are typically pretreated to achieve uniform orientation of the liquid crystal material.
  • the display modes according to the present invention preferably use an electric field that is substantially parallel to the compound layer.
  • Liquid crystal compositions suitable for LCDs and especially for IPS displays are e.g. from JP 07-181 439 (A), EP 0 667 555, EP 0 673 986, DE 195 09 410, DE 195 28 106, DE 195 28 107,
  • WO 96/23 851 and WO 96/28 521 have serious disadvantages. Most of them, among other shortcomings, lead to unfavorably long response times, have too low resistivity values, and / or require operating voltages that are too high. There is also a need to improve the low temperature performance of the LCDs. Here, both an improvement of the operating characteristics, as well as the shelf life and, in particular, the stability to visible light and UV radiation, but also against heat and especially against a combination of heat and light and / or UV radiation necessary.
  • Polymerization inhibitor and, in particular in combination with UV absorbers, used as light or UV protection.
  • Polypropylene is used for the automotive industry and garden furniture.
  • Cyasorb UV-3853S contains 50% HALS in an LDPE resin and a mixture of different HALS, wherein the alkyl radical “R” in Cyasorb UV-3853S substantially “Cn to C 20 " alkyl and predominantly "C 16 to C 18 "alkyl. According to NA / 867, 09.01.2001, NICAS, Government of Australia, "Cyasorb UV-3852S” contains 50% polyethylene and the HALS component of "Cyasorb UV-3852S” esters of the following acids:
  • liquid crystalline media found. Many liquid crystal media, especially those with large polarities, or high dielectric anisotropy, do not meet those for practical
  • liquid-crystalline media with suitable properties for practical applications, such as a broad nematic phase range, suitable optical anisotropy ⁇ corresponding to the type of display used, a high ⁇ and especially low viscosities for particularly short switching times.
  • liquid-crystalline media can be realized with a suitably high ⁇ , a suitable phase range and suitable An, which the disadvantages of
  • R 11 to R 14 are each independently of one another alkyl having 1 to 4 C atoms, preferably all four CH 3 ,
  • X 1 H or O * ie a single-bonded O atom with a free-radical electron, preferably O * ,
  • Z 1 is -O-, - (CO) -O-, -O- (CO) -, -O- (CO) -O-, -NH-, -NY 01 - or
  • Y 1 and Y 01 are each independently of one another straight-chain or branched alkyl having 1 to 20 C atoms, preferably having 1 to 10 C atoms and particularly preferably having 1 5 C atoms, also cycloalkyl, cycloalkylalkyl, or
  • Alkylcyloalkyl wherein in all these groups one or more -CH 2 - groups can be replaced by -O- so that in the molecule no two O-atoms are directly connected to each other, means and, in the case where Z 1 is -0- (CO) -O-,
  • R 2 and R 3 are each independently alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms and preferably R 2 and R 3 is alkyl or alkenyl, L 21 , L 22 , L 31 and L are independently H or F,
  • X 2 and X 3 independently of one another are halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms, preferably F, Cl, -OCF 3 or -CF 3 , very preferably F, Cl or -OCF3,
  • R 41 and R 42 independently of one another have the meanings given above under formula II for R 2 , preferably R 41 is alkyl and R 42 is alkyl or alkoxy or R 41 is alkenyl and R 42 is alkyl, independently of each other and in case of double occurrences of also these independently
  • the compounds of the formulas II and III are preferably dielectrically positive compounds, preferably with a dielectric anisotropy of more than 3.
  • the compounds of formula IV are preferably dielectrically neutral compounds, preferably with a dielectric anisotropy in the
  • the liquid-crystalline media according to the present application preferably contain a total of 10 ppm to 10,000 ppm, preferably 50 ppm to 2,000 ppm, and very particularly preferably 100 ppm to 1,000 ppm of compounds of the formula I.
  • Liquid crystal mixtures stabilize the "Voltage Holding Ratio" (short VHR or only HR) of the mixtures after UV exposure.
  • the individual compounds of the formula II and / or III are used in a concentration of 1 to 20%, preferably from 1 to 15%. These limits apply in particular if in each case two or more homologous compounds, ie compounds of the same formula, are used. If only one single substance, ie only one homologue, of the compounds of one formula is used, its concentration can be in the range from 2 to 20%, preferably from 3 to 14%.
  • the media according to the invention each contain one or more compounds of the formula IA selected from the group of Compounds of the formulas 1-1 to I-7, preferably of the formulas 1-1 and / or I-2:
  • the media according to the invention each contain one or more compounds of the formula I selected from the group of the following compounds
  • R and R ' are each independently of the above at Y 1
  • alkyl particularly preferably n-alkyl.
  • the media according to the invention each contain one or more compounds of the formula I selected from the group of the following compounds of the formulas 1-1 a-1, 1-1 a-2, 1-1 b-1 to 1-1b-4, 1-5a-1, 1-5a-2, 1-6a-1 and 1-6a-2, most preferably selected from the group of compounds 1-1a-1, 1- 1 a-2, 1-1 b-1 and 1-1 b-2 and most preferably selected from the group of compounds of formulas 1-1 a-1 and 1-1 a-2:
  • the media according to the present invention contain, in addition to the compounds of the formula I, or their preferred sub-formulas, one or more dielectrically positive compounds having a dielectric anisotropy of more than 3, selected from the group of the formulas II and III.
  • the media of the invention contain one or more
  • the media according to the present invention comprise, alternatively or in addition to the compounds of the formulas III-1 and / or III-2, one or more compounds of the formula III-3
  • the media according to the invention preferably contain one or more compounds selected from the group of the compounds of the formulas II-1 to II-4, in which L 21 and L 22 and / or L 23 and L 24 are both F.
  • the media contain one or more compounds selected from the group of
  • the media contain one or more compounds of formula II-1.
  • the compounds of the formula II-1 are preferably selected from the group of the compounds of the formulas II-1a to II-1f
  • L 21 and L 22 both mean F
  • L 21 and L 22 are both F and / or L 23 and L 24 are both F and in formula II-1e L 21 , L 22 and L 25 are F and in each case the other parameters d have respective meanings given above.
  • R 2 has the meaning given above.
  • the media contain one or more compounds of formula II-2, which are preferably selected from the group of
  • L 25 to L 28 independently of one another are H or F, preferably L 27 and L 28 are both H, particularly preferably L 26 H and the other parameters are the respective meanings given above.
  • the media of the invention contain one or more compounds selected from the group of compounds of formulas II-2a to II-2j, wherein L 2 and L 22 both F and / or L 23 and L 24 are both F and the other parameters are the respective have the meanings given above.
  • the media according to the invention contain one or more compounds selected from the group of compounds of the formulas II-2a to II-2j, wherein L 21 , L 22 , L 23 and L 24 all denote F and the other parameters are the respective ones above given meanings.
  • Especially preferred compounds of formula II-2 are the compounds of the following formulas
  • R 2 and X 2 have the meanings given above and X 2 is preferably F.
  • the media according to the invention comprise one or more compounds of the formula 11-3, preferably selected from the group of the compounds of the formulas II-3a to II-3c
  • L 2 and L 22 are preferably both F.
  • the media according to the invention comprise one or more compounds of the formula II-4, preferably of the formula II-4a
  • X 2 is preferably F or OCF 3l particularly preferably F means.
  • the media according to the invention preferably comprise one or more compounds of the formula III-1, preferably selected from the group of the compounds of the formulas I I-1 a and
  • the media according to the invention comprise one or more compounds of the formula III-1a, preferably selected from the group of the compounds of the formulas III-1a-1 to III-1a-6 wherein R 3 has the meaning given above.
  • the media according to the invention preferably comprise one or more compounds of the formula III-1b, preferably selected from the group of the compounds of the formulas III-1b-1 to HM b-4, preferably of the formula II 1-1 b-4 wherein R 3 has the meaning given above.
  • the media according to the invention preferably contain one or more compounds of the formula III-2, preferably selected from the group of the compounds of the formulas III-2a to III-2j
  • the parameters have the meaning given above and preferably wherein the parameters have the respective meanings given above and the parameters L 33 , L 34 , L 35 and L 36 independently of one another and from the other parameters H or F.
  • the media according to the invention preferably comprise one or more compounds of the formula III-2a, preferably selected from the group of the compounds of the formulas III-2a-1 to III-2a-5
  • R 3 has the meaning given above.
  • the media according to the invention preferably comprise one or more compounds of the formula III-2b, preferably selected from the group of the compounds of the formulas III-2b-1 and III-2b-2, preferably of the formula III-2b-2
  • R 3 has the meaning given above.
  • the media according to the invention preferably contain one or more compounds of the formula III-2c, preferably selected from the group of the compounds of the formulas III-2c-1 to III-2c-6
  • R 3 has the meaning given above.
  • the media according to the invention preferably contain one or more compounds selected from the group of the compounds of the formulas III-2d and III-2e, preferably selected from the group of the compounds of the formulas III-2d-1 and III-2e-1
  • R 3 has the meaning given above.
  • the media according to the invention preferably comprise one or more compounds of the formula III-2f, preferably selected from the group of the compounds of the formulas III-2f-1 to III-2f-5 wherein R 3 has the meaning given above.
  • the media according to the invention comprise one or more compounds of the formula III-2g, preferably selected from the group of the compounds of the formulas III-2g-1 to III-2g-5
  • R 3 has the meaning given above.
  • the media according to the invention preferably contain one or more compounds of the formula III-2h, preferably selected from the group of the compounds of the formulas III-2h-1 to III-2h-3, preferably of the formula III-2h-3
  • the media according to the invention preferably contain one or more compounds of the formula ⁇ -2i, preferably selected from the group of the compounds of the formulas ⁇ -2i-1 and ⁇ -2i-2, particularly preferably of the formula III-2i-2
  • the media according to the invention preferably contain one or more compounds of the formula III-2j, preferably selected from the group of the compounds of the formulas III-2j-1 and III-2j-2, particularly preferably of the formula III-2j-1
  • the media according to the present invention may contain one or more compounds of the formula III-3
  • R 3 has the meaning given above.
  • the liquid-crystalline media according to the present invention contain a dielectrically neutral component, component C.
  • This component has a dielectric anisotropy in the range of -1.5 to 3.
  • it contains dielectrically neutral compounds having a dielectric anisotropy in the range of -1.5 to 3, more preferably it consists predominantly, even more preferably it consists essentially and especially preferably consists entirely of it.
  • this component contains one or more dielectrically neutral compounds, more preferably it is predominantly, even more preferably substantially, and most preferably it consists entirely of dielectrically neutral compounds having a dielectric anisotropy in the range of -1, 5 to 3, of the formula IV.
  • the dielectrically neutral component, component C contains one or more compounds selected from the group of compounds of formulas IV-IV-8
  • R 41 is preferably alkyl or alkenyl, preferably alkenyl, and R 42 is preferably alkyl or alkenyl, preferably alkyl
  • R 41 and R 42 are preferably alkyl.
  • R 41 is preferably alkyl or alkenyl, more preferably alkyl
  • R 42 is preferably alkyl, alkenyl or alkoxy, more preferably alkenyl or alkoxy
  • R 41 is preferably alkyl and R 42 is preferably alkyl or alkoxy, more preferably alkoxy.
  • the dielectrically neutral component, component C contains one or more compounds selected from the group of compounds of formulas IV-1, IV-5, IV-6 and IV-7, preferably one or more compounds of formula IV-1 and one or more compounds selected from the group of the formulas IV-5 and IV-6, more preferably in each case one or more compounds of the formulas IV-1, IV-5 and IV-6 and very preferably in each case one or more compounds of formulas IV-1, IV-5, IV-6 and IV-7.
  • the media of the invention contain one or more compounds of formula IV-4, more preferably selected from their respective sub-formulas of formula CP-Vn and / or CP-nV-m and / or CP-Vn-m, more preferably Formula CP-Vn and / or CP-V2-n and most preferably selected from the group of the formulas CP-V-1 and CP-V2-1.
  • formula IV-4 more preferably selected from their respective sub-formulas of formula CP-Vn and / or CP-nV-m and / or CP-Vn-m, more preferably Formula CP-Vn and / or CP-V2-n and most preferably selected from the group of the formulas CP-V-1 and CP-V2-1.
  • the media of the invention contain one or more compounds of formula IV-5, more preferably selected from their respective sub-formulas of formula CCP-Vn and / or CCP-nV-m and / or CCP-Vn-m, more preferably Formula CCP-Vn and / or CCP-V2-n and most preferably selected from the group of the formulas CCP-V-1 and CCP-V2-1.
  • the definitions of these abbreviations are given below in Table D, or from Tables A to C.
  • the media according to the invention comprise one or more compounds of the formula IV-1, more preferably selected from their respective sub-formulas, the formula CC-nm, CC-nV, CC-n-Vm, CC-VV, CC -V-Vn and / or
  • CC-nV-Vm more preferably of the formulas CC-nV and / or CC-n-Vm and most preferably selected from the group of the formulas CC-3-V, CC-4-V, CC-5-V CC-3 -V1, CC-4V1, CC-5-V1, CC-3-V2 and CC-V-V1.
  • the definitions of these abbreviations are also given below in Table D, or from Tables A to C.
  • the liquid-crystal mixtures according to the present invention contain the component C, the compounds of the formula IV selected from the group of compounds of the formula Formulas IV-1 to IV-8 as shown above and optionally of the formulas IV-9 to IV-15 contains, preferably predominantly consists thereof and quite preferably consists entirely of:
  • R 41 and R 42 independently of one another are alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, Alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms and
  • the media of the invention contain one or more compounds of formula IV-10, more preferably selected from their respective sub-formulas of formula CPP-3-2, CPP-5-2 and CGP-3-2, more preferably of formula CPP -3-2 and / or CGP-3-2 and most preferably the formula CPP-3-2.
  • the definitions of these abbreviations are given below in Table D, or from Tables A to C.
  • liquid-crystalline media preferably comprise one or more compounds of the formula V wherein
  • R 51 and R 52 independently of one another have the meanings given above under formula II for R 2 , preferably R 51
  • Alkyl and R is alkyl or alkenyl
  • O mean, preferably one or more of
  • the compounds of formula V are preferably dielectrically neutral compounds having a dielectric anisotropy in the range of -1, 5 to 3.
  • the media according to the invention preferably contain one or more compounds selected from the group of the compounds of the formulas V-1 and V-2
  • the media according to the invention preferably comprise one or more compounds selected from the group of the compounds of the formulas V-1 and V-2, in which R 5 is preferably n-alkyl and in formula V-1 R 52 is preferably alkenyl and in formula V-2 R 52 is preferably n-alkyl.
  • the media of the invention contain one or more compounds of formula V-1, more preferably their sub-formula PP-n-2Vm, even more preferably of formula PP-1-2V1.
  • the definitions of these abbreviations are given below in Table D, or from Tables A to C.
  • the media of the present invention more preferably contain one or more compounds of Formula V-2, more preferably their sub-formulas PGP-nm, PGP-nV, PGP-n-2Vm, PGP-n-2V and PGP-n-2Vm preferably their sub-formulas PGP-3-m, PGP-n-2V and PGP-n-V1, most preferably selected from the formulas PGP-3-2, PGP-3-3, PGP-3-4, PGP-3-5 , PGP-1-2V, PGP-2-2V and
  • the media according to the present invention may contain one or more dielectrically positive compounds of the formula VI
  • the media according to the present invention contain one or more compounds of formula VI, preferably selected
  • the compounds of the formula VI-1 are preferably selected from the group of the compounds of the formulas VI-1a and VI-b wherein R 6 has the meaning given above.
  • the compounds of the formula VI-2 are preferably selected from the group of the compounds of the formulas VI-2a to VI-2d
  • liquid-crystal media according to the present invention may contain one or more compounds of formula VII wherein
  • R ' has the meaning given above under formula II for R 2 , one of the rings of
  • the compounds of the formula VII are preferably dielectrically positive compounds.
  • the liquid-crystal media according to the present invention may contain one or more compounds of the formula VIII wherein independently of one another have the meaning given above for R 2 under formula II, and
  • the compounds of the formula VIII are preferably dielectrically negative compounds.
  • the media according to the invention preferably comprise one or more compounds of the formula VIII, preferably selected from the group of the compounds of the formulas VIII-1 to VIII-3
  • R 81 and R 82 have the respective meanings given above under formula VIII.
  • R 81 is preferably n-alkyl or 1-E-alkenyl and R 82 is preferably n-alkyl or alkoxy.
  • liquid-crystalline media according to the present invention contain one or more compounds selected from the group of compounds of formulas I to VIII, preferably
  • compositions in this application, means that the entity in question, ie the medium or component, contains the indicated component or components or compound or compounds, preferably in a total concentration of 10% or more, and more preferably 20%. or more.
  • Predominantly consist of in this context means that the entity in question contains 55% or more, preferably 60% or more, and more preferably 70% or more of the indicated component or components or compound or compounds.
  • Substantially consisting of in this context means that the entity in question contains 80% or more, preferably 90% or more and most preferably 95% or more of the indicated component or components or compound or compounds.
  • the liquid crystal media according to the present invention preferably have a clearing point of 70 ° C or more, more preferably 75 ° C or more, more preferably 80 ° C or more, and most preferably 85 ° C or more.
  • the nematic phase of the inventive media extends at least from 0 ° C or less to 70 ° C or more, more preferably at least from -20 ° C or less to 75 ° C or more, most preferably at least -30 ° C or less to 75 ° C or more and especially at least from -40 ° C or less to 80 ° C or more.
  • the ⁇ of the liquid crystal medium according to the invention at 1 kHz and 20 ° C is preferably 2 or more, more preferably 3 or more, even more preferably 4 or more, and most preferably 6 or more.
  • ⁇ is 30 or less, more preferably ⁇ is 20 or less.
  • the ⁇ of the liquid crystal media according to the present invention is preferably 589 nm (Na D ) and 20 ° C in the range of 0.070 or more to 0.150 or less, more preferably in the range of 0.080 or more to 0.140 or less, still more preferably in the range from 0.090 or more to 0.135 or less and most preferably in the range of 0.100 or more to 0.130 or less.
  • the ⁇ of the liquid-crystal media according to the present invention is the ⁇ of the liquid-crystal media according to the present invention
  • Invention preferably 0.080 or more to 0.120 or less, stronger preferably in the range of 0.090 or more to 0.110 or less and most preferably in the range of 0.095 or more to 0.105 or less, while ⁇ preferably in the range of 6 or more to
  • the nematic phase of the media of the invention preferably extends at least from -20 ° C or less to 70 ° C or more, more preferably at least from -20 ° C or less to 70 ° C or more, most preferably at least -30 ° C or less to 70 ° C or more and especially at least from -40 ° C or less to 70 ° C or more.
  • present invention preferably 0.100 or more to 0.140 or less, more preferably in the range of 0.110 or more to 0.130 or less and most preferably in the range of 0.115 or more to 0.125 or less, while ⁇ preferably in the range of 7 or more to 13 or less, preferably in the range of 9 or more to
  • the nematic phase of the media of the invention preferably extends at least from -20 ° C or less to 80 ° C or more, more preferably at least from -20 ° C or less to 85 ° C or more, even more preferably at least -30 ° C or less to 80 ° C or more and especially at least from -40 ° C or less to 85 ° C or more.
  • the compounds of formula I are preferably together in the media in a total concentration of from 1% to 50%, more preferably from 1% to 30%, more preferably from 2% to 30%, more preferably from 3% to 30% %, and more preferably from 5% to 25% of the total mixture.
  • the compounds selected from the group of formulas II and III are preferably used in a total concentration of from 2% to 60%, more preferably from 3% to 35%, even more preferably from 4% to 20% and most preferably from 5% to 15%. the total mixture used.
  • the compounds of formula IV are preferably in a
  • the compounds of formula V are preferably in a
  • the compounds of formula VI are preferably in a
  • the media of the invention may contain other liquid crystal compounds to adjust the physical properties.
  • Such compounds are known to the person skilled in the art.
  • Their concentration in the media according to the present invention is preferably 0% to 30%, more preferably 0.1% to 20%, and most preferably 1% to 15%.
  • the concentration of the compound of the formula CC-3-V in the media according to the invention can, in a preferred embodiment, be 50% to 65%, more preferably 55% to 60%.
  • the liquid-crystal media preferably contain a total of 50% to 100%, more preferably 70% to 100% and most preferably 80% to 100% and especially 90% to 100% of the compounds of formulas I to VII, preferably selected from the group of compounds of Formulas of the formulas IA, IB and II to VI, particularly preferably of the formulas I to V, in particular of the formulas IA, IB, II, III, IV, V and VII and very particularly preferably of the formulas IA, IB, II, III, IV and V. Preferably, they are predominantly of this, and most preferably, they are almost entirely composed thereof.
  • the liquid crystal media each contain one or more
  • dielectrically positively describes compounds or components , dielectrically neutral with and dielectrically negative with , is determined at a frequency of 1 kHz and 20 ° C.
  • the dielectric anisotropy of each compound is determined from the results of a solution of 10% of each individual compound in a nematic host mixture. If the solubility of each compound in the host mixture is less than 10%, the concentration is reduced to 5%.
  • the capacities of the test mixtures are determined in a cell with homeotropic as well as homogeneous orientation. The layer thickness is about 20 pm in both cell types.
  • the applied voltage is a square wave with a frequency of 1 kHz and one
  • Constants of the compounds are determined from the change in the respective values of the host mixture upon addition of the compounds of interest. The values are extrapolated to a concentration of the compounds of interest of 100%. Components which have a nematic phase at the measuring temperature of 20 ° C are measured as such, all others are treated as compounds.
  • threshold voltage refers to in the present
  • the optical threshold is reported for 10% relative contrast (Vi 0 ), the term saturation voltage refers to the optical saturation and is given for 90% relative contrast (V 90 ), in both cases, unless expressly stated otherwise.
  • the capacitive threshold voltage (V 0 ), also called the Freedericks threshold V Fr is only used if expressly stated
  • the optical anisotropy ( ⁇ ) is determined at a wavelength of 589.3 nm.
  • the dielectric anisotropy ( ⁇ ) is determined at a frequency of 1 kHz.
  • the threshold voltages as well as all other electro-optical properties are determined with test cells manufactured at Merck KGaA, Germany. The test cells for the determination of ⁇ have a layer thickness of approximately 20 ⁇ m.
  • the electrode is a circular ITO
  • An electrode with an area of 1, 13 cm 2 and a guard ring From- Directional layers are SE-1211 from Nissan Chemicals, Japan, for homeotropic alignment (sn) and polyimide AL-1054 from Japan Synthetic Rubber, Japan, for homogeneous alignment ( ⁇ ⁇ ). Capacitance is determined using a Solatron 1260 frequency response analyzer using a sine wave with a voltage of 0.3 V ⁇ . The light used in the electro-optical measurements is white light. In this case, a structure with a commercially available device DMS Fa. Autronic Melchers, Germany is used. The characteristic
  • Threshold voltage (V 10 ), mid-gray voltage (V 50 ) and saturation voltage (V 90 ) were determined for 10%, 50% and 90% relative contrast, respectively.
  • the liquid-crystal media according to the present invention may include further additives and chiral dopants in the usual concentrations.
  • the total concentration of these other ingredients is in the range of 0% to 10%, preferably 0.1% to 6%, based on the total mixture.
  • the concentrations of the individual compounds used are preferably each in the range of 0.1% to 3%.
  • the concentration of these and similar additives is not taken into account in the specification of the values and concentration ranges of the liquid crystal components and compounds of the liquid crystal media in this application.
  • the liquid-crystal media according to the invention consist of several compounds, preferably from 3 to 30, more preferably from 4 to 20 and most preferably from 4 to 16 compounds. These compounds are mixed in a conventional manner. In general, the desired amount of the compound used in the smaller amount is dissolved in the compound used in the larger amount. If the temperature is above the clearing point of the compound used in the higher concentration, the completion of the dissolution process is particularly easy to observe.
  • the media in other conventional ways, for example using so-called premixes, which may for example be homologous or eutectic mixtures of compounds, or using so-called multi-bottle systems whose components are themselves ready-to-use mixtures.
  • liquid crystal media of the present invention can be modified to be useful in all known types of liquid crystal displays, either by using the liquid crystal media per se, such as TN, TN-AMD, ECB-AMD, VAN-AMD , IPS-AMD, F-FS-AMD LCDs or in
  • Composite systems such as PDLC, NCAP, PN LCDs and especially in ASM-PA LCDs.
  • Table A the codes used for the ring elements of the core structures of the compounds are listed, while in Table B, the linking groups are shown.
  • Table C gives the meanings of the codes for the left and right end groups. The acronyms are composed of the codes for the ring elements with optional join groups, followed by a first hyphen and the codes for the left end group, as well as a second hyphen and the codes for the right end group.
  • Table D summarizes example structures of compounds with their respective abbreviations.
  • n and m are integers and the three dots "" are placeholders for other abbreviations in this table.
  • n, m and I are preferably independently from 1 to 7.
  • the mesogenic media contain one or more compounds selected from the group of compounds of Table E.
  • example compounds are summarized, which can be used in the mesogenic media according to the present invention preferably as chiral dopants.
  • the mesogenic media contain one or more compounds selected from the group of compounds of Table F.
  • the mesogenic media according to the present application contain two or more, preferably four or more, compounds selected from the group consisting of the compounds of the above tables.
  • the liquid-crystal media according to the present invention preferably contain seven or more, preferably eight or more, individual compounds, preferably three or more, more preferably four or more more, different formulas selected from the group of compounds of Table D.
  • Mix M1 This mixture (mix M1) is prepared and divided into four parts. The first part is examined without adding another compound. To the three further parts of the mixture are added 100 ppm, 200 ppm and 500 ppm of the compound to be tested, here the compound of formula I-1a-2. There are four test cells each with the
  • Orientation layer AL-16301 (Japan Synthetic Rubber (JSR), Japan) and examined for their voltage holding ratio.
  • the initial value and the value after 2 hours of UV exposure are determined in a Suntest device from Heraeus, Germany. In each case the HR is measured at a temperature of 100 ° C, after 5 minutes in the oven. The results are summarized in the following table.
  • Contain compound of formula I is characterized in particular by excellent stability to UV irradiation. In this case, the stability increases with increasing concentration of the compound of formula 1-1 a-2 in these three mixtures.
  • the temperature stability is checked by a heat test.
  • the HR is determined before and after heat exposure.
  • the heat load is applied to the bulk liquid crystal material by storing 2 g of the material in a sealed glass bottle for 4 hours in an oven at a temperature of 150 ° C.
  • the mixture M1 is prepared and divided here into two parts. The first part is examined without adding another compound. Become the second part of the mix
  • the mixture M1 is prepared and divided again into four parts. The first part is examined without adding another compound.
  • the mixture M1 is prepared and divided into two parts. The first part will be without adding another
  • the stabilizing effect is weaker here than in Examples 1 and 2. However, it should be noted that the
  • Concentration of the compounds of formula I in Cyasorb UV3852-S is only 50%, and that these compounds have predominantly long Aklyl or alkenyl chains and thus have a high molecular weight. As a result, the average concentration of the active N-containing molecular units, as compared to the compounds used in Examples 1 and 2, is also reduced.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

L'invention concerne des milieux à cristaux liquides diélectriquement positifs contenant un ou plusieurs composés représentés par la formule (I) dans laquelle les paramètres ont les significations respectives indiquées dans le descriptif, éventuellement un ou plusieurs autres composés diélectriquement positifs et éventuellement un ou plusieurs autres composés diélectriquement neutres. L'invention concerne également des écrans à cristaux liquides contenant ces milieux, notamment des écrans à matrice active et particulièrement des écrans NT, IPS et FFS.
PCT/EP2011/005889 2010-12-07 2011-11-23 Milieu à cristaux liquides et écran à cristaux liquides Ceased WO2012076121A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102010053591.5 2010-12-07
DE102010053591 2010-12-07
DE102011010381 2011-02-05
DE102011010381.3 2011-02-05

Publications (2)

Publication Number Publication Date
WO2012076121A1 true WO2012076121A1 (fr) 2012-06-14
WO2012076121A8 WO2012076121A8 (fr) 2012-08-16

Family

ID=45047713

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/005889 Ceased WO2012076121A1 (fr) 2010-12-07 2011-11-23 Milieu à cristaux liquides et écran à cristaux liquides

Country Status (3)

Country Link
DE (1) DE102011119144A1 (fr)
TW (1) TWI541333B (fr)
WO (1) WO2012076121A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105384681A (zh) * 2014-09-02 2016-03-09 默克专利股份有限公司 化合物和液晶介质

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104334688A (zh) 2012-06-05 2015-02-04 默克专利股份有限公司 液晶介质和液晶显示器
KR20160098586A (ko) * 2015-02-09 2016-08-19 삼성디스플레이 주식회사 액정 조성물, 이를 포함하는 액정 표시 장치 및 그 제조 방법
DE102015003602A1 (de) 2015-03-18 2016-09-22 Merck Patent Gmbh Flüssigkristalines Medium
CN110325620A (zh) * 2017-02-21 2019-10-11 默克专利股份有限公司 液晶介质和包含其的液晶显示器

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991005029A1 (fr) 1989-10-02 1991-04-18 MERCK Patent Gesellschaft mit beschränkter Haftung Systeme mesomorphe electro-optique
DE4000451A1 (de) 1990-01-09 1991-07-11 Fraunhofer Ges Forschung Elektrooptisches fluessigkristallschaltelement
EP0588568A2 (fr) 1992-09-18 1994-03-23 Hitachi, Ltd. Dispositif d'affichage à cristal liquide
JPH07181439A (ja) 1993-12-24 1995-07-21 Hitachi Ltd アクティブマトリクス型液晶表示装置
EP0667555A1 (fr) 1994-02-14 1995-08-16 Hitachi, Ltd. Dispositif d'affichage à cristal liquide à matrice active
EP0673986A2 (fr) 1994-03-17 1995-09-27 Hitachi, Ltd. Dispositif d'affichage à cristaux liquides à matrice active
WO1996023851A1 (fr) 1995-02-03 1996-08-08 Merck Patent Gmbh Affichage electro-optique a cristaux liquides
DE19528106A1 (de) 1995-02-03 1996-08-08 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
DE19528107A1 (de) 1995-03-17 1996-09-19 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
WO1996028521A1 (fr) 1995-03-15 1996-09-19 Merck Patent Gmbh Affichage electro-optique a cristaux liquides
DE102008016053A1 (de) * 2007-04-24 2008-10-30 Merck Patent Gmbh Flüssigkristallines Medium und Flüssigkristallanzeige
EP2085454A1 (fr) * 2008-02-01 2009-08-05 MERCK PATENT GmbH Milieu à cristaux liquides et affichage à cristaux liquides

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991005029A1 (fr) 1989-10-02 1991-04-18 MERCK Patent Gesellschaft mit beschränkter Haftung Systeme mesomorphe electro-optique
DE4000451A1 (de) 1990-01-09 1991-07-11 Fraunhofer Ges Forschung Elektrooptisches fluessigkristallschaltelement
EP0588568A2 (fr) 1992-09-18 1994-03-23 Hitachi, Ltd. Dispositif d'affichage à cristal liquide
JPH07181439A (ja) 1993-12-24 1995-07-21 Hitachi Ltd アクティブマトリクス型液晶表示装置
EP0667555A1 (fr) 1994-02-14 1995-08-16 Hitachi, Ltd. Dispositif d'affichage à cristal liquide à matrice active
EP0673986A2 (fr) 1994-03-17 1995-09-27 Hitachi, Ltd. Dispositif d'affichage à cristaux liquides à matrice active
WO1996023851A1 (fr) 1995-02-03 1996-08-08 Merck Patent Gmbh Affichage electro-optique a cristaux liquides
DE19528106A1 (de) 1995-02-03 1996-08-08 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
WO1996028521A1 (fr) 1995-03-15 1996-09-19 Merck Patent Gmbh Affichage electro-optique a cristaux liquides
DE19509410A1 (de) 1995-03-15 1996-09-19 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
DE19528107A1 (de) 1995-03-17 1996-09-19 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
DE102008016053A1 (de) * 2007-04-24 2008-10-30 Merck Patent Gmbh Flüssigkristallines Medium und Flüssigkristallanzeige
EP2085454A1 (fr) * 2008-02-01 2009-08-05 MERCK PATENT GmbH Milieu à cristaux liquides et affichage à cristaux liquides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Stand", November 1997, MERCK KGAA, article "Merck Liquid Crystals, Physical Properties of Liquid Crystals"
MIEVILLE, P. ET AL., ANGEW. CHEM., vol. 122, 2010, pages 6318 - 6321
PASCAL MIÉVILLE ET AL: "Scavenging Free Radicals To Preserve Enhancement and Extend Relaxation Times in NMR using Dynamic Nuclear Polarization", ANGEWANDTE CHEMIE, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 122, no. 35, 16 August 2010 (2010-08-16), pages 6318 - 6321, XP008149284, ISSN: 0044-8249, [retrieved on 20100721], DOI: 10.1002/ANGE.201000934 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105384681A (zh) * 2014-09-02 2016-03-09 默克专利股份有限公司 化合物和液晶介质
CN105384681B (zh) * 2014-09-02 2019-11-19 默克专利股份有限公司 化合物和液晶介质

Also Published As

Publication number Publication date
WO2012076121A8 (fr) 2012-08-16
DE102011119144A1 (de) 2012-06-14
TWI541333B (zh) 2016-07-11
TW201231628A (en) 2012-08-01

Similar Documents

Publication Publication Date Title
DE102009010580B4 (de) Flüssigkristallines Medium und und dessen Verwendung in einer Flüssigkristallanzeige
DE102009006322B4 (de) Flüssigkristallines Medium und seine Verwendung in einer Flüssigkristallanzeige
DE102009005747B4 (de) Flüssigkristallines Medium und seine Verwendung in einer Flüssigkristallanzeige
DE102008046379B4 (de) Flüssigkristallines Medium und dessen Verwendung in einer Flüssigkristallanzeige
EP3327102B1 (fr) Milieu à base de cristaux liquides et dispositif d'affichage à base de cristaux liquides
WO2008128623A1 (fr) Milieux de cristaux liquides et écrans à cristaux liquides
DE102010018170A1 (de) Flüssigkristallines Medium und Flüssigkristallanzeige
DE102009006272B4 (de) Flüssigkristallines Medium und dessen Verwendung in einer Flüssigkristallanzeige
DE102009004764B4 (de) Flüssigkristallines Medium und seine Verwendung in einer Flüssigkristallanzeige
DE102009010578B4 (de) Flüssigkristallines Medium und Flüssigkristallanzeige
EP2516588B1 (fr) Milieu cristal liquide et dispositifs d'affichage à base de cristaux liquides
EP3112441A1 (fr) Milieu a cristaux liquides et affichage a cristaux liquides
DE102010015824B4 (de) Flüssigkristallines Medium und Flüssigkristallanzeige
WO2012076121A1 (fr) Milieu à cristaux liquides et écran à cristaux liquides
DE102008046250B4 (de) Flüssigkristallines Medium und seine Verwendung in Flüssigkristallanzeigen
DE102010049441B4 (de) Flüssigkristallines Medium für Flüssigkristallanzeigen
WO2009121458A1 (fr) Milieu cristallin liquide et affichage à cristaux liquides

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11788374

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11788374

Country of ref document: EP

Kind code of ref document: A1