WO2012052104A1 - Milieu cristallin liquide et écran à cristaux liquides - Google Patents

Milieu cristallin liquide et écran à cristaux liquides Download PDF

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Publication number
WO2012052104A1
WO2012052104A1 PCT/EP2011/004801 EP2011004801W WO2012052104A1 WO 2012052104 A1 WO2012052104 A1 WO 2012052104A1 EP 2011004801 W EP2011004801 W EP 2011004801W WO 2012052104 A1 WO2012052104 A1 WO 2012052104A1
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compounds
formula
independently
formulas
atoms
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PCT/EP2011/004801
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German (de)
English (en)
Inventor
Markus Czanta
Michael Junge
Atsutaka Manabe
Elvira Montenegro
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Merck Patent Gmbh
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Publication of WO2012052104A1 publication Critical patent/WO2012052104A1/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
    • C09K19/52—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 crystalline media and liquid crystal displays containing these media, especially to displays addressed by an active matrix, and more particularly to twisted nematic (TN) displays in plane switching (IPS) or fringe field
  • 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 in-plane switching (IPS) mode (such 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 in-plane switching
  • FFS Fringe Field Switching
  • LCDs in modern desktop monitors and are intended for use in displays for televisions and multimedia applications
  • the 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.
  • liquid-crystalline media with lower viscosities ( ⁇ ), especially with lower rotational viscosities ( ⁇ - ⁇ ) required.
  • the rotational viscosity should be 80 mPa ⁇ s or less, preferably 60 mPa ⁇ s or less and especially 55 mPa ⁇ s or less, especially for monitor applications.
  • the media must have a range of the nematic phase of suitable width and position, as well as a suitable birefringence ( ⁇ ) and 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 12.
  • 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.
  • PDLC p_olymer dispersed liquid crystal
  • NCAP non-nematic curvilinearly aligned p.hase
  • PN systems polymer network
  • 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, in particular against a combination of heat and light and / or UV radiation necessary.
  • octocrylene commercially available under the name octocrylene, is known and is z. B. used in formulations for cosmetic products, such as skin creams and sunscreens as UV protection.
  • WO 2009/129911 A proposes the compound "DABCO” in addition to so-called “HALS” as a second, additional stabilizer in dielectrically negative liquid-crystal mixtures.
  • 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 having a suitably high ⁇ , a suitable phase range and ⁇ can be realized which do not have the disadvantages of the materials of the prior art or at least only to a considerably lesser extent.
  • R 11 straight-chain or branched alkyl having 1 to 12 C-atoms, preferably 2-ethyl-hexyl, each independently H, straight-chain or branched alkyl having 1 to 8 carbon atoms, preferably having 1 to 4 carbon atoms, or straight-chain or branched alkoxy having 1 to 8 C atoms, preferably having 1 to 4 C atoms, preferably both H,
  • Y 1 is H, Cl or CN, preferably CN, and
  • B 11 to B are each independently of one another H, F, straight-chain or branched alkyl having 1 to 8 C atoms, preferably having 1 to 4 C atoms, or straight-chain or branched alkoxy having 1 to 8 C atoms, preferably 1 to 4 C atoms, preferably all H, or alternatively one or more of
  • R 2 and R 3 denotes alkyl or alkenyl, at each appearance independently
  • L 21 , L, L and L independently of one another H or F, preferably L 21 and / or L 31 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 -OCF 3 ,
  • n is preferably 0, 1 or 2 and more preferably 1 or
  • R 41 and R 42 independently of one another have the meaning given above for R 2 under formula II, 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
  • Particularly preferred compounds of the formula I are compounds in which Y 1 is CN.
  • Very particularly preferred here is the compound 2-ethylhexyl-2-cyano-3,3-diphenyl, commercially available under the name octocrylene, for example under the name Eusolex® OCR from the company. Merck KGaA.
  • 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 IA and / or of the formula IB, preferably of the formula IA. These compounds are outstandingly suitable as stabilizers in
  • 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
  • R 11 has the meaning given above under formula IA.
  • the media according to the invention each contain one or a plurality of compounds of the formula IA selected from the group of the compounds of the formulas IA-1a and IA-2a, preferably of the formula IA-1a:
  • the media according to the invention each contain one or more compounds of the formula IB selected from the group of
  • R 11b to R 1 are each independently of one another H, F, straight-chain or branched alkyl having 1 to 8 C atoms, preferably having 1 to 4 C atoms, or straight-chain or branched alkoxy having 1 to 8 C atoms, preferably 1 to 4 C atoms, preferably all H, or alternatively one or more of
  • R 11a to R 14a are phenylene.
  • the media according to the invention each contain one or more compounds of the formula IB selected from the group of the compounds of the formulas IB-1a to IB-1g, IB-2a, IB-3a, IB-3b and IB 4 a, IB-4, preferably of the formula IB-a:
  • the media according to the present invention contain in addition to the compounds selected from the group of
  • dielectric anisotropy greater than 3 selected from the group of formulas II and III.
  • the media according to the invention contain one or more
  • the media according to the present invention contain, as an alternative 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 11-1 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 11-1.
  • the compounds of the formula 11-1 are preferably selected from the group of the compounds of the formulas 11-1a to 11f wherein the parameters have the respective meanings given above and L 23 to L 25 independently of one another and of the other parameters H or F mean and
  • L 21 and L 22 both mean F
  • L 21 and L 22 both F and / or L 23 and L 24 are both F and in formula 11-1 e
  • L 21 , L 22 and L 25 are F and in each case the other parameters have the respective meanings given above.
  • Especially preferred compounds of formula 11-1 are
  • 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 21 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 11-2 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 21 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 3 , more 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 III-1a and
  • the media according to the invention preferably contain 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
  • R 3 has the meaning given above.
  • the media according to the invention preferably contain one or more compounds of the formula III-1b, preferably selected from the group of the compounds of the formulas III-1 B-1 to III-1 B-4, preferably of the formula III-1b-4
  • the media according to the invention contain one or more compounds of the formula II 1-2, preferably selected from the group of the compounds of the formulas III-2a to III-2j
  • 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
  • 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 comprise one or more compounds of the formula ⁇ -2 ⁇ , preferably selected from the group of the compounds of the formulas ⁇ -2 ⁇ -1 and III-2i-2, preferably of the formula III-2i-2
  • the inventive media 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, 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, more preferably It consists predominantly, even more preferably consists essentially and quite preferably consists entirely of dielectrically neutral compounds having a dielectric anisotropy in the range of -1, 5 to 3, the formula IV.
  • the dielectrically neutral component, component C contains one or more compounds selected from the group of compounds of formulas IV-1 to IV-8
  • R 41 is preferably alkyl or alkenyl, preferably alkenyl, and R 42 is preferably alkyl or alkenyl, preferably alkyl in Formula IV-2
  • R 4 and R 42 are preferably alkyl
  • in formula IV-5 R 41 is preferably alkyl or alkenyl, more preferably alkyl, and R 42 is preferably alkyl, alkenyl or alkoxy, more preferably alkenyl or alkoxy and in formulas IV-4 and IV-8
  • 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 the formula CP-Vn and / or CP-nV-m and / or CP-Vn-m, more preferably the 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 definitions of these abbreviations (acronyms) are given below in Table D, or from Tables A to C.
  • 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 of the 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 (acronyms) are given below in Table D, or from Tables A to C.
  • the media according to the invention contain 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 comprise component C, the compounds of formula IV selected from the group of compounds of formula IV -1 to IV-8 as shown above and optionally containing the formulas IV-9 to IV-15, preferably predominantly consists thereof and quite preferably completely consists thereof:
  • R and R 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 C 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 (acronyms) are given below in Table D, or from Tables A to C.
  • the liquid-crystalline media according to the present invention 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
  • the compounds of the formula V are preferably dielectrically neutral compounds having a dielectric anisotropy in the range of -1.5 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 contain one or more compounds selected from the group of compounds of formulas V-1 and V-2, wherein R 51 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
  • R 6 denotes alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms and preferably alkyl or alkenyl,
  • the media according to the present invention comprise one or more compounds of the formula VI, preferably selected from the group of the compounds of the formulas VI-1
  • the compounds of the formula VI-1 are preferably selected from the group of the compounds of the formulas VI-1a and VI-1b
  • the compounds of the formula VI-2 are preferably selected from the group of the compounds of the formulas VI-2a to VI-2d
  • R 6 has the meaning given above.
  • liquid-crystal media according to the present invention may contain one or more compounds of formula VII
  • R 7 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.
  • liquid-crystal media according to the present invention may contain one or more compounds of the formula VIII
  • R 81 and R 82 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 and R have the respective meanings given above under formula VIII.
  • R 81 is preferably n-alkyl or 1-E-alkenyl and R is preferably n-alkyl or alkoxy.
  • the liquid-crystalline media according to the present invention preferably contain one or more compounds selected from the group of the compounds of the formulas I to VIII, preferably of the formulas I to VII and more preferably of the formulas I and II and / or III and / or IV and / or VI. Most preferably, they are predominantly, even more preferably essentially, and most preferably, completely composed.
  • compositions in this application, means that the entity in question, ie the medium or component, the specified component or components, or Contains compound or compounds, preferably in a total concentration of 10% or more, and more preferably of 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 media of the invention 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, even more 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 liquid crystal media according to the present invention is preferably 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, even more preferably in the range of 589 nm (Na D ) and 20 ° C 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, more 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 11 or less, preferably in the range of 7 or more to 10 or less, and more preferably in the range of 8 or more to 9 or less.
  • 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 is more to 13 or less, preferably in the range of 9 or more to 12 or less, and more preferably in the range of 10 or more to 1 or less.
  • 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 taken together in the media in a total concentration of
  • 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
  • Total concentration from 0% to 50%, more preferably from 1% to 40%, even more preferably from 5% to 30% and most preferably from 10% to 20% of the total mixture.
  • 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 in a preferred embodiment may 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 the formulas I to VII, preferably selected from the group of the compounds of the 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 thereof, and most preferably, they are almost entirely composed thereof.
  • the liquid crystal media each contain one or more
  • dielectrically positive describes compounds or components with ⁇ > 3.0, dielectrically neutral with -1.5 ⁇ ⁇ 3.0 and dielectrically negative with ⁇ ⁇ -1.5.
  • ⁇ 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 for both types of cells.
  • the applied voltage is a square wave with a frequency of 1 kHz and an effective value of typically 0.5V to 1.0V, but is always chosen to be below the capacitive threshold for the particular test mixture.
  • 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 about 20 pm.
  • the electrode is a circular ITO electrode with an area of 1.13 cm 2 and a guard ring.
  • the alignment layers are SE-1211 from Nissan Chemicals, Japan, for homeotropic alignment ( ⁇ ⁇ ⁇ ) 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 Vrm S.
  • the light used in the electro-optical measurements is white light.
  • a structure with a commercially available device DMS Fa. Autronic Melchers, Germany is used.
  • the characteristic stresses were determined under vertical observation.
  • the threshold voltage (Vi 0 ), mid-gray voltage (V 5 o) 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 used in indicating the values and concentration ranges of the liquid crystal components and Compounds of the liquid-crystal media are not considered 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.
  • premixes which may be e.g. may be homologous or eutectic mixtures of compounds, or using so-called "multi-bottle" systems, the ingredients of which 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.
  • 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.
  • Table E-1 example compounds are listed which may be included in the mesogenic media according to the present invention and which may be used as stabilizers.
  • the mesogenic media contain one or more compounds selected from the group of the compounds of Table E-2.
  • Table E-2 example compounds are listed which can be used in the mesogenic media according to the present invention as additional stabilizers.
  • the mesogenic media contain one or more compounds selected from the group of the compounds of Table E-2.
  • 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
  • This mixture (mix M1) is prepared and divided into four parts. The first part is examined without adding another compound. To the other three parts of the mixture are added 100 ppm, 500 ppm, and 1000 ppm of the compound to be tested. Two test cells each are filled with the orientation layer AL-16301 (Japan Synthetic Rubber (JSR), Japan) and examined for their constitutional holding ratio. The initial value and the value after 2
  • 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 M3 was divided into four parts and examined as described in Example 1. The results are summarized in the following table.
  • the concentration here is 500 ppm.
  • an additional UV irradiation is carried out over a period of 24 hours.
  • the stabilizing effect of the compound DABCO can be seen here particularly well after UV irradiation over a period of 24 h.

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

Abstract

La présente invention concerne des milieux cristallins liquides diélectriquement positifs contenant un ou plusieurs composés sélectionnés dans le groupe constitué par les composés des formules (IA) et (IB) dans lesquelles les paramètres ont les significations respectives indiquées dans la description, et éventuellement un ou plusieurs autres composés diélectriquement positifs et éventuellement un ou plusieurs composés diélectriquement neutres. L'invention concerne par ailleurs des affichages à cristaux liquides contenant lesdits milieux, en particulier des affichages à matrice active et notamment des affichages TN, IPS et FFS.
PCT/EP2011/004801 2010-10-23 2011-09-26 Milieu cristallin liquide et écran à cristaux liquides WO2012052104A1 (fr)

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DE102010049441.0 2010-10-23
DE102010049441.0A DE102010049441B4 (de) 2010-10-23 2010-10-23 Flüssigkristallines Medium für Flüssigkristallanzeigen

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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
DE19528106A1 (de) 1995-02-03 1996-08-08 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
WO1996023851A1 (fr) 1995-02-03 1996-08-08 Merck Patent Gmbh Affichage electro-optique a cristaux liquides
WO1996028521A1 (fr) 1995-03-15 1996-09-19 Merck Patent Gmbh Affichage electro-optique a cristaux liquides
DE19528107A1 (de) 1995-03-17 1996-09-19 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
FR2899462A1 (fr) * 2006-04-06 2007-10-12 Oreal Emulsion huile dans eau a base de globules huileux pourvus d'un enrobage cristal liquide lamellaire contenant un filtre uv lipophile et le phytantriol sous forme de gel cubique ; utilisations
WO2009129911A1 (fr) 2008-04-22 2009-10-29 Merck Patent Gmbh, Milieu cristal liquide

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
DE19528106A1 (de) 1995-02-03 1996-08-08 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
WO1996023851A1 (fr) 1995-02-03 1996-08-08 Merck Patent Gmbh Affichage electro-optique a cristaux liquides
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
FR2899462A1 (fr) * 2006-04-06 2007-10-12 Oreal Emulsion huile dans eau a base de globules huileux pourvus d'un enrobage cristal liquide lamellaire contenant un filtre uv lipophile et le phytantriol sous forme de gel cubique ; utilisations
WO2009129911A1 (fr) 2008-04-22 2009-10-29 Merck Patent Gmbh, Milieu cristal liquide

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TWI503405B (zh) 2015-10-11
TW201229215A (en) 2012-07-16
DE102010049441A1 (de) 2012-04-26
DE102010049441B4 (de) 2019-05-09

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