EP1629064A1 - Cristal liquide - Google Patents

Cristal liquide

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Publication number
EP1629064A1
EP1629064A1 EP04739214A EP04739214A EP1629064A1 EP 1629064 A1 EP1629064 A1 EP 1629064A1 EP 04739214 A EP04739214 A EP 04739214A EP 04739214 A EP04739214 A EP 04739214A EP 1629064 A1 EP1629064 A1 EP 1629064A1
Authority
EP
European Patent Office
Prior art keywords
compounds
alkyl
liquid
formulas
crystalline medium
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.)
Withdrawn
Application number
EP04739214A
Other languages
German (de)
English (en)
Inventor
Michael Heckmeier
Volker Reiffenrath
Izumi Saito
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
Priority to EP10009551A priority Critical patent/EP2295520A3/fr
Publication of EP1629064A1 publication Critical patent/EP1629064A1/fr
Withdrawn legal-status Critical Current

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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
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3048—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • 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
    • C09K2019/0459—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 -CF=CF- chain, e.g. 1,2-difluoroethen-1,2-diyl
    • 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition

Definitions

  • the present invention relates to a liquid-crystalline medium, its use for electro-optical purposes and displays containing this medium.
  • Liquid crystals are mainly used as dielectrics in display devices, since the optical properties of such substances can be influenced by an applied voltage.
  • Electro-optical devices based on liquid crystals are well known to the person skilled in the art and can be based on various effects. Such devices are, for example, cells with dynamic scattering, DAP cells (deformation of aligned phases), guest / host cells, TN cells with a twisted nematic ("twisted nematic”) structure, STN cells (“super-twisted nematic”), SBE cells (“superbirefringence effect”) and OMI cells (“optical mode interference”).
  • the most common display devices are based on the Schadt-Helfrich effect and have a twisted nematic structure.
  • the liquid crystal materials must have good chemical and thermal stability and good stability against electric fields and electromagnetic radiation. Furthermore, the liquid crystal materials should have a low viscosity and give short response times, low threshold voltages and a high contrast in the cells.
  • nematic or cholesteric mesophase for the above-mentioned cells.
  • liquid crystals are generally used as mixtures of several components, it is important that the components are readily miscible with one another.
  • Other properties, such as electrical conductivity, dielectric anisotropy and optical anisotropy, have to meet different requirements depending on the cell type and area of application suffice. For example, materials for cells with a twisted nematic structure should have positive dielectric anisotropy and low electrical conductivity.
  • media with large positive dielectric anisotropy, wide nematic phases, relatively low birefringence, very high resistivity, good UV and temperature stability and lower vapor pressure are desired for matrix liquid crystal displays with integrated non-linear elements for switching individual pixels (MLC displays).
  • Such matrix liquid crystal displays are known.
  • active elements i.e. transistors
  • non-linear elements for the individual switching of the individual pixels.
  • active matrix whereby one can distinguish two types:
  • MOS Metal Oxide Semiconductor
  • TFT Thin film transistors
  • the TN effect is usually used as the electro-optical effect.
  • TFTs made from compound semiconductors such as CdSe or TFT's based on polycrystalline or amorphous silicon The latter technology is being worked on with great intensity worldwide.
  • the TFT matrix is applied to the inside of one glass plate of the display, while the other glass plate carries the transparent counter electrode on the inside. Compared to the size of the The pixel electrode of the TFT is very small and practically does not disturb the image.
  • This technology can also be expanded for fully color-compatible image representations, with a mosaic of red, green and blue filters being arranged in such a way that one filter element each is opposite a switchable image element.
  • the TFT displays usually work as TN cells with crossed polarizers in transmission and are illuminated from behind.
  • MLC displays of this type are particularly suitable for TV applications (e.g. pocket TVs) or for high-information displays for computer applications (laptops) and in automobile or aircraft construction.
  • TV applications e.g. pocket TVs
  • high-information displays for computer applications (laptops)
  • automobile or aircraft construction In addition to problems with the angle dependency of the contrast and the switching times, problems arise with MFK displays due to the insufficiently high specific resistance of the
  • Liquid crystal mixtures [TOGASHI, S., SEKOGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, p. 141 ff, Paris; STROMER, M., Proc. Eurodisplay 84, Sept. 1984: Design of Thin Film Transistors for
  • the object of the invention is to provide media, in particular for such MFK, TN or STN displays, which do not have the disadvantages indicated above or only to a lesser extent, and preferably at the same time have very high specific resistances and low threshold voltages.
  • the invention thus relates to a liquid-crystalline medium based on a mixture of polar compounds, characterized in that it contains one or more compounds of the formula I,
  • L 1 and L 2 are each independently H or F
  • the mixtures according to the invention based on a mixture of polar compounds with positive dielectric anisotropy are preferably suitable for monitor and TV applications, since they are characterized by low rotational viscosities ( ⁇ -i) and high ⁇ n values.
  • the mixtures according to the invention are particularly suitable for TN-TFT monitor applications and in applications with 5V drivers or with drivers with higher voltages. Due to the broad nematic phase of the compounds of formula I and the very good ⁇ / T N ⁇ ratio, the mixtures according to the invention are particularly suitable for TN-TFT and IPS applications.
  • the compounds of the formulas I have a wide range of applications and are known in part from published patent applications EP 0 727 406 A1, WO 95/30723 and EP 0 571 916 A1. Depending on the selection of the substituents, these compounds can serve as base materials from which liquid-crystalline media are predominantly composed; However, it is also possible to add compounds of the formula I to liquid-crystalline base materials from other classes of compounds, for example in order to influence the dielectric and / or optical anisotropy of such a dielectric and / or to optimize its threshold voltage and / or its viscosity.
  • the compounds of the formulas I are colorless in the pure state and form liquid-crystalline mesophases in a temperature range which is favorably located for electro-optical use. They are stable chemically, thermally and against light.
  • X in the compounds of the formula I preferably denotes F, Cl, CN, NCS, CF 3) SF 5 , CF 2 H, OCF 3 , OCF 2 H, OCFHCF3, OCFHCFH 2 , OCFHCF2H, OCF2CH 3 , OCF 2 CFH2, OCF 2 CF 2 H, OCF 2 CF 2 CF 2 H, OCF 2 CF 2 CFH 2) OCFHCF2CF3, OCFHCF2CF 2 H, OCFHCFHCF3, OCH 2 CF 2 CF 3 , OCF 2 CF 2 CF 3) OCF 2 CFHCFH 2 , OCF 2 CH 2 CF 2 H,
  • OCFHCF2CFH2 OCFHCF2CFH2, OCFHCFHCF 2 H, OCFHCH 2 CF 3, OCH 2 CFHCF 3, OCH 2 CF 2 CF 2 H, OCF2CFHCH 3, OCF 2 CH 2 CFH 2, OCFHCF 2 CH 3, OCFHCFHCFH 2, OCFHCH 2 CF 3, OCH 2 CF 2 CFH 2 , OCH 2 CFHCF 2 H, OCF 2 CH 2 CH 3 , OCFHCFHCH 3 , OCFHCH 2 CFH 2 , OCH2CF2CH3, OCH 2 CFHCFH 2 , OCH 2 CH 2 CF 2 H, OCHCHCH 2 CH 3 , OCH 2 CFHCH 3>
  • OCF 2 CCIFCFH2 OCF 2 CF 2 CCI 2 F, OCF2CCI2CF 2 H, OCF 2 CH 2 CClF 2, OCCIFCF 2 CFH2, OCFHCF 2 CCI 2 F, OCCIFCFHCF 2 H, OCCIFCCIFCF 2 H, OCFHCFHCCIF 2, OCCIFCH 2 CF 3, OCFHCCI 2 CF 3 , OCCI 2 CFHCF 3 , OCH 2 CCIFCF 3 , OCCI 2 CF 2 CF 2 H, OCH 2 CF 2 CCIF 2 , OCF 2 CCIFCH 3 , OCF 2 CFHCCI 2 H, OCF 2 CCI 2 CFH 2 , OCF 2 CH 2 CCI 2 F, OCCIFCF 2 CH 3 ,
  • X preferably denotes F or OCF 3 .
  • L 1 and L 2 are preferably H.
  • R 1 is preferably alkenyl.
  • R 1 in formula I is an alkyl radical and / or an alkoxy radical, this can be straight-chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 carbon atoms and accordingly preferably means ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, also methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy or tetradedoxy.
  • R 1 is an alkyl radical in which one Ch ⁇ group has been replaced by -O- and one has been replaced by -CO-, these are preferably adjacent.
  • these include an acyloxy group -CO-O- or an oxycarbonyl group -O-CO-. These are preferably straight-chain and have 2 to 6 carbon atoms.
  • acryloyloxymethyl 2-acryloyloxyethyl, 3-acryloyloxypropyl, 4-acryloyloxybutyl, 5-acryloyloxypentyl, 6-acryloyloxyhexyl, 7-acryloyloxyheptyl, 8-acryloyloxyoctyl, 9-acryloyloxynonyl, 10-acryloyloxyloxyloxyloxyloxyloxyl Methacryloyloxyethyl, 3-methacryloyloxypropyl, 4-methacryloyloxybutyl, 5-methacryloyloxypentyl, 6-methacryloyloxyhexyl, 7-methacryloyloxyheptyl, 8-methacryloyloxyoctyl, 9-methacryloyloxynonyl.
  • R 1 is an alkyl or alkenyl radical which is simply substituted by CN or CF 3 , this radical is preferably straight-chain. The substitution by CN or CF 3 is in any position.
  • R 1 is an alkyl or alkenyl radical which is at least monosubstituted by halogen
  • this radical is preferably straight-chain and halogen is preferably F or Cl.
  • halogen is preferably F.
  • the resulting residues also include perfluorinated residues.
  • the fluorine or chlorine substituent can be in any position, but preferably in the ⁇ position.
  • Compounds with branched wing groups R 1 can occasionally be important because of their better solubility in the usual liquid-crystalline base materials, but in particular as chiral dopants if they are optically active. Smectic compounds of this type are suitable as components for ferroelectric materials. Branched groups of this type usually contain no more than one chain branch.
  • R 1 represents an alkyl radical in which two or more CH 2 groups have been replaced by -O- and / or -CO-O-, this can be straight-chain or branched. It is preferably branched and has 3 to 12 carbon atoms.
  • it means especially bis-carboxy-methyl, 2,2-bis-carboxy-ethyl, 3,3-bis-carboxy-propyl, 4,4-bis-carboxy-butyl, 5,5-bis-carboxy-pentyl, 6,6-bis-carboxy-hexyl, 7,7-bis-carboxy-heptyl, 8,8-bis-carboxy-octyl, 9,9-bis-carboxy-nonyl, 10,10-bis-carboxy-decyl, Bis (methoxycarbonyl) methyl, 2,2-bis (methoxycarbonyl) ethyl, 3,3 bis (methoxycarbonyl) propyl, 4,4-bis (methoxycarbonyl) butyl, 5, 5-bis (methoxycarbonyl) pentyl, 6,6-bis (methoxycarbonyl) hexyl, 7,7-bis (methoxycarbonyl) heptyl, 8,8-bis (
  • the compounds of the formulas I are prepared by methods known per se, as described in the literature (for example in the standard works such as Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart), under reaction conditions that are known and suitable for the above-mentioned implementations. Use can also be made of variants which are known per se and are not mentioned here in detail.
  • the compounds of formula I can, for. B. be prepared as described in WO 95/30723.
  • the invention also relates to electro-optical displays (in particular STN or MFK displays with two plane-parallel carrier plates which form a cell with a border, integrated non-linear elements for switching individual pixels on the carrier plates and a nematic liquid crystal mixture in the cell with positive dielectric anisotropy and high specific resistance) which contain such media and the use of these media for electro-optical purposes.
  • electro-optical displays in particular STN or MFK displays with two plane-parallel carrier plates which form a cell with a border, integrated non-linear elements for switching individual pixels on the carrier plates and a nematic liquid crystal mixture in the cell with positive dielectric anisotropy and high specific resistance
  • liquid crystal mixtures according to the invention allow a significant expansion of the available parameter space.
  • the liquid crystal mixtures according to the invention enable clearing points above 60 ° C., preferably above 65 ° C., particularly preferably above 70 ° C., while maintaining the nematic phase down to -20 ° C. and preferably up to -30 ° C., particularly preferably up to -40 ° C. at the same time to achieve dielectric anisotropy values ⁇ > 6, preferably> 8 and a high value for the specific resistance, whereby excellent STN and MFK displays can be achieved.
  • the mixtures are characterized by small operating voltages.
  • the TN thresholds are generally below 2.0 V, preferably below 1.9 V, particularly preferably £ 1.8 V.
  • the MFK displays according to the invention preferably operate in the first transmission minimum according to Gooch and Tarry [CH. Gooch and HA Tarry, Electron. Lett. 10, 2-4, 1974; CH. Gooch and HA Tarry, Appl. Phys., Vol.
  • the flow viscosity V 20 at 20 ° C. is preferably ⁇ 60 mm 2 s "1 , particularly preferably ⁇ 50 mm 2 s " 1 .
  • the rotational viscosity ⁇ i of the mixtures according to the invention at 20 ° C. is preferably ⁇ 120 mPa-s, particularly preferably ⁇ 100 mPa-s, very particularly preferably ⁇ 80 mPa-s.
  • the nematic phase range is preferably at least 90 °, in particular at least 100 °. This range preferably extends at least from -20 ° to + 80 °.
  • a short switching time is desirable for liquid crystal displays. This is especially true for ads that are capable of video playback. Switching times (total: ton +) of maximum 25 ms are required for such displays. The upper limit of the switching time is determined by the refresh rate.
  • the UV stability of the mixtures according to the invention is also considerably better, i.e. they show a significantly smaller decrease in HR under UV exposure.
  • the mixtures according to the invention preferably contain little ( ⁇ 10% by weight) or no nitriles.
  • the values for the holding ratio of the mixtures according to the invention are preferably> 98%, in particular> 99% at 20 ° C.
  • Particularly preferred compounds of the formula I are compounds of the formulas 1-1 to 1-15:
  • R 1 has the meaning given in formula I.
  • R in the compounds of the formulas 1-1 to 1-15 is preferably alkenyl, in particular 1-alkenyl or 3-alkenyl.
  • the medium contains one, two or more compounds of the formulas 1-1 to 1-15;
  • the medium contains the connection
  • the medium preferably contains one or more two-core compounds of the formula K.
  • the proportion of compounds K in the mixture is 5-40%, preferably 5-30%, in particular 5-20%.
  • Particularly preferred dual-core compounds are the compounds of the formulas K-1 to K-27
  • the medium additionally contains one or more compounds selected from the group consisting of the general formulas II to VI:
  • Y 1 to Y 4 each independently of one another H or F,
  • the medium additionally contains one or more compounds selected from the group consisting of the general formulas VII to XIII: where R, 0, X v 0 and i ⁇ Yy1-4 each independently of one another in
  • X ° is preferably F, Cl, CF 3 , OCF 3 or OCHF 2 .
  • R ° preferably denotes alkyl, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 carbon atoms.
  • the medium additionally contains one or more compounds of the formulas E-a to E-d,
  • R ° has the meanings given in claim 3;
  • the proportion of the compounds of the formulas Ea to Ed is preferably 10-30% by weight, in particular 15-25% by weight;
  • the proportion of compounds of the formulas I to VI together is at least 50% by weight in the mixture as a whole;
  • the proportion of compounds of the formula I in the mixture as a whole is 0.5 to 40, particularly preferably 1 to 30,% by weight;
  • the proportion of compounds of the formulas II to VI in the mixture as a whole is 30 to 80% by weight;
  • the medium contains compounds of the formulas II, III, IV, V and / or VI;
  • R ° is straight-chain alkyl or alkenyl with 2 to 7 carbon atoms
  • the medium consists essentially of compounds of the formulas I to VI and XIII;
  • the medium contains further compounds, preferably selected from the following group consisting of the general formulas XIV to XVIII:
  • 1,4-phenylene rings can additionally be substituted by CN, chlorine or fluorine.
  • the 1,4-phenylene rings are preferably substituted one or more times by fluorine atoms.
  • the medium additionally contains one, two, three or more, preferably two or three compounds of the formulas
  • the medium preferably contains 5-35% by weight of compound IVa.
  • the medium preferably contains one, two or three compounds of the formula IVa, in which X ° F or OCF 3 .
  • the medium preferably contains one or more compounds of the formulas Ha to IIg,
  • R has the meanings given above.
  • R ° preferably denotes methyl, ethyl, n-propyl, n-butyl and n-pentyl.
  • the medium preferably contains one or more two- and / or three-core connections with a CF 2 O bridge of the formulas Q-1 to Q-15:
  • R ° has the compounds given above.
  • the compound Q-12 is particularly preferred, furthermore Q-6.
  • the mixture according to the invention preferably contains 3-20%, in particular 3-15%, of the compounds of the formulas Q-1 to Q-15.
  • the weight ratio (I): (II + III + IV + V + VI) is preferably 1:10 to 10: 1.
  • the medium essentially consists of compounds selected from the group consisting of the general formulas I to XIII.
  • the proportion of the compounds of the formula IVb and / or IVc in which X ° is fluorine and R ° is CH 3 , C 2 H 5 , nC 3 H 7 , nC H 9 or nC 5 Hn is from 2 to 20% by weight in the mixture as a whole. , in particular 2 to 15% by weight;
  • the medium preferably contains compounds of the formulas II to VI, in which R ° denotes methyl.
  • the medium particularly preferably contains compounds of
  • the medium preferably contains one, two or more, preferably one or two, dioxone compounds of the formulas
  • the medium additionally contains one, two or more two-core compounds of the formulas Z-1 to Z-8
  • R 1a and R 2a each independently represent H, CH3, C 2 Hs or nC 3 H 7 .
  • R °, alkyl and alkyl * have the meanings given in claim 3 or below.
  • the compounds Z-1, Z-2, Z-5, Z-6, Z-7 and Z-8 are particularly preferred.
  • the mixtures according to the invention preferably contain 5-40%, in particular
  • the medium additionally contains one or more compounds of the formulas P-1 to P-8
  • the medium additionally contains one, two or more compounds with fused rings of the formulas AN1 to AN11:
  • alkyl or “alkyl *” encompasses straight-chain and branched alkyl groups having 1-7 carbon atoms, in particular the straight-chain groups methyl, ethyl, propyl, butyl, pentyl, hexyl and heptyl. Groups with 1-5 carbon atoms are generally preferred.
  • alkenyl encompasses straight-chain and branched alkenyl groups with 2-7 carbon atoms, in particular the straight-chain groups.
  • Preferred alkenyl groups are C 2 -C 7 -1 E-alkenyl, C 4 -C 7 -3E-alkenyl, C 5 -C 7 -4-alkenyl, C 6 -C 7 -5-alkenyl and C 7 -6-alkenyl , in particular C 2 -C 7 -1 E-alkenyl, C -C 7 -3E-alkenyl and C 5 -C 7 -4-alkenyl.
  • alkenyl groups are vinyl, 1 E-propenyl, 1 E-butenyl, 1 E-pentenyl, 1 E-hexenyl, 1 E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4- Pentenyl, 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl, 6-heptenyl and the like. Groups of up to 5 carbon atoms are generally preferred.
  • fluoroalkyl preferably encompasses straight-chain groups with terminal fluorine, i.e. Fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorhexyl and 7-fluoroheptyl. However, other positions of the fluorine are not excluded.
  • oxaalkyl preferably includes straight-chain radicals of the formula CnH 2 n + rO- (CH 2 ) m, in which n and m each independently represent 1 to 6.
  • Response times, the threshold voltage, the steepness of the transmission characteristics etc. can be modified in the desired manner.
  • 1 E-alkenyl residues, 3E-alkenyl residues, 2E-alkenyloxy residues and the like generally lead to shorter response times, improved nematic tendencies and a higher ratio of the elastic constants k 33 (bend) and kn (splay) compared to alkyl or alkoxy residues.
  • 4-alkenyl residues, 3-alkenyl residues and the like generally give lower threshold voltages and smaller values of k 33 / kn in comparison to alkyl and alkoxy residues.
  • a -CH 2 CH 2 group generally leads to higher values of k 33 / kn compared to a simple covalent bond.
  • Higher values of k 33 / n allow, for example, flatter transmission characteristics in TN cells 90 ° twist (to achieve gray tones) and steeper transmission characteristics in STN, SBE and OMI cells (higher multiplexability) and vice versa.
  • III + IV + V + VI largely depends on the desired properties, on the choice of components of the formulas I, II, III, IV, V and / or VI and on the choice of further components which may be present.
  • the total amount of compounds of the formulas I to XIII in the mixtures according to the invention is not critical.
  • the mixtures can therefore contain one or more further components in order to optimize various properties.
  • the observed effect on the response times and the threshold voltage is generally greater the higher the total concentration of compounds of the formulas I to XIII.
  • a favorable synergistic effect with the compounds of the formulas I leads to particularly advantageous properties.
  • Mixtures containing compounds of the formula I and the formula IVa in particular are notable for their low threshold voltage.
  • Electrode base plates and electrodes with surface treatment speaks of the usual design for such displays.
  • the term of the conventional design is broad here and also includes all modifications and modifications of the MLC display, in particular also matrix display elements based on poly-Si TFT or MIM.
  • liquid crystal mixtures which can be used according to the invention are prepared in a manner which is customary per se.
  • the desired amount of the components used in smaller amounts is dissolved in the components which make up the main constituent, advantageously at elevated temperature. It is also possible to dissolve the components in an organic solvent, e.g. in acetone, chloroform or methanol, and to remove the solvent after thorough mixing, for example by distillation.
  • the dielectrics can also contain further additives known to the person skilled in the art and described in the literature. For example, 0-15% pleochroic dyes, UV stabilizers, antioxidants or chiral dopants can be added. Suitable dopants and stabilizers are listed in Tables C and D.
  • C means a crystalline, S a smectic, S c a smectic C, N a nematic and I the isotropic phase.
  • V-io denotes the voltage for 10% transmission (viewing direction perpendicular to the plate surface)
  • ton denotes the switch-on time and the switch-off time for an operating voltage corresponding to 2.0 times the value of V-io.
  • ⁇ n denotes the optical anisotropy.
  • the electro-optical data are measured in a TN cell at the 1st minimum (ie at a d • ⁇ n value of 0.5 ⁇ m) at 20 ° C, unless expressly stated otherwise.
  • the optical data are measured at 20 ° C, unless expressly stated otherwise.
  • Liquid-crystalline mixtures which, in addition to the compounds of the formulas I, contain at least one, two, three or four compounds from Table B are particularly preferred. Table C.
  • Table C shows possible dopants which are generally added to the mixtures according to the invention in a concentration of 0.1 to 10% by weight, in particular 0.1 to 6% by weight.
  • Stabilizers which can be added, for example, to the mixtures according to the invention up to a maximum of 10% by weight, preferably 0.001-8% by weight, in particular 0.05-5% by weight, are mentioned below:

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
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  • Liquid Crystal Substances (AREA)
  • Steroid Compounds (AREA)

Abstract

L'invention concerne un cristal liquide à base d'un mélange de composés polaires, qui se caractérise en ce qu'il contient au moins un composé correspondant à la formule (I), formule dans laquelle R1, L1 et L2 correspondent aux définitions données dans la revendication (1). L'invention concerne également l'utilisation de ce cristal liquide à des fins électro-optiques, en particulier dans des moniteurs TN.
EP04739214A 2003-05-21 2004-05-14 Cristal liquide Withdrawn EP1629064A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10009551A EP2295520A3 (fr) 2003-05-21 2004-05-14 Milieu liquide crystallin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10322908 2003-05-21
PCT/EP2004/005234 WO2004104137A1 (fr) 2003-05-21 2004-05-14 Cristal liquide

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EP04739214A Withdrawn EP1629064A1 (fr) 2003-05-21 2004-05-14 Cristal liquide

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JP (1) JP2007504340A (fr)
KR (1) KR20060003116A (fr)
CN (1) CN100480355C (fr)
DE (1) DE102004024456B4 (fr)
TW (1) TW200502365A (fr)
WO (1) WO2004104137A1 (fr)

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Publication number Publication date
CN100480355C (zh) 2009-04-22
KR20060003116A (ko) 2006-01-09
TW200502365A (en) 2005-01-16
DE102004024456B4 (de) 2016-05-12
EP2295520A3 (fr) 2011-08-03
US7419705B2 (en) 2008-09-02
CN1791659A (zh) 2006-06-21
WO2004104137A1 (fr) 2004-12-02
US20070034830A1 (en) 2007-02-15
JP2007504340A (ja) 2007-03-01
DE102004024456A1 (de) 2004-12-09
EP2295520A2 (fr) 2011-03-16

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