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EP0995184A1 - Affichage a cristaux liquides ferroelectriques a large spectre de temperature de travail - Google Patents

Affichage a cristaux liquides ferroelectriques a large spectre de temperature de travail

Info

Publication number
EP0995184A1
EP0995184A1 EP98941322A EP98941322A EP0995184A1 EP 0995184 A1 EP0995184 A1 EP 0995184A1 EP 98941322 A EP98941322 A EP 98941322A EP 98941322 A EP98941322 A EP 98941322A EP 0995184 A1 EP0995184 A1 EP 0995184A1
Authority
EP
European Patent Office
Prior art keywords
replaced
diyl
atoms
display
different
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Withdrawn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
EP98941322A
Other languages
German (de)
English (en)
Inventor
Ayako Takeichi
Barbara Hornung
Hans-Rolf DÜBAL
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.)
Aventis Research and Technologies GmbH and Co KG
Original Assignee
Hoechst Research and Technology Deutschland GmbH and Co KG
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 Hoechst Research and Technology Deutschland GmbH and Co KG filed Critical Hoechst Research and Technology Deutschland GmbH and Co KG
Publication of EP0995184A1 publication Critical patent/EP0995184A1/fr
Withdrawn legal-status Critical Current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
    • C09K19/04—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)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C09K19/588—Heterocyclic compounds
    • 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
    • G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
    • G02F1/139—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on orientation effects in which the liquid crystal remains transparent
    • G02F1/141—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on orientation effects in which the liquid crystal remains transparent using ferroelectric liquid crystals
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09G—ARRANGEMENTS OR CIRCUITS FOR CONTROL OF INDICATING DEVICES USING STATIC MEANS TO PRESENT VARIABLE INFORMATION
    • G09G3/00—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes
    • G09G3/20—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters
    • G09G3/34—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters by control of light from an independent source
    • G09G3/36—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters by control of light from an independent source using liquid crystals
    • G09G3/3611—Control of matrices with row and column drivers
    • G09G3/3622—Control of matrices with row and column drivers using a passive matrix
    • G09G3/3629—Control of matrices with row and column drivers using a passive matrix using liquid crystals having memory effects, e.g. ferroelectric liquid crystals
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09G—ARRANGEMENTS OR CIRCUITS FOR CONTROL OF INDICATING DEVICES USING STATIC MEANS TO PRESENT VARIABLE INFORMATION
    • G09G2310/00—Command of the display device
    • G09G2310/06—Details of flat display driving waveforms

Definitions

  • liquid crystals Due to the unusual combination of anisotropic and fluid behavior, liquid crystals have found a large number of possible uses in electro-optical switching and display devices.
  • smectic liquid crystal phases in particular ferroelectric (FLC), have also been used in recent years.
  • FLC ferroelectric
  • FLC light valves Ferroelectric liquid crystal mixtures
  • LC light valves are devices that e.g. change their optical transmission or reflection properties due to electrical shading in such a way that incident or reflected light is intensity-modulated. Examples are the well-known clock and calculator displays or LC displays in the field of office communication and television.
  • the viscosity is temperature-dependent as follows: ⁇ (T) ⁇ exp V / k b T
  • the invention therefore relates to a ferroelectric liquid crystal display comprising a ferroelectric liquid crystal mixture, characterized in that the display is driven by voltage pulses of longer than 0.9 ms.
  • the invention also relates to an above-mentioned display with improved temperature dependence of the working voltage.
  • Another object of the invention is a method for producing a ferroelectric liquid crystal display with improved temperature dependence of the working voltage, characterized in that the ferroelectric liquid crystal mixture and the electrical control are matched to one another in such a way that the product from spontaneous polarization (in nano-Coulomb /
  • Square centimeters and the width of the voltage pulses used for the control is greater than 15, preferably 20, particularly preferably 100, in particular 500.
  • the invention also relates to a method for improving the
  • Temperature dependence of the working voltage of an FLC display characterized in that the display is controlled with voltage pulses which are longer than 0.9 ms.
  • the display according to the invention is particularly suitable for applications in which very fast switching is not necessary. Such displays can be switched with the same voltage over a very wide temperature range; there is no need to adjust the voltage depending on the temperature.
  • the required working voltages are very low, they can be below 15V, sometimes below 5V, in particular even below 3V.
  • Applications are therefore, for example, displays in chip cards, electronic price or display signs (shelf labels), PDAs (Personal Digital Assistants) or
  • the display according to the invention is constructed in such a way that an FLC layer is enclosed on both sides by layers which, starting from the FLC layer, are usually at least one orientation layer, electrodes and a boundary plate (e.g. made of glass or plastic). They also contain at least one polarizer if they are operated in the "guest-host" or in the reflective mode, or two polarizers if the mode used is transmissive birefringence.
  • the switching and display elements can optionally further auxiliary layers, such as diffusion barrier or
  • the orientation layer (s) are usually rubbed films made from organic polymers or obliquely evaporated silicon oxide.
  • phase sequence of the liquid crystal mixture with decreasing temperature is:
  • the planar orientation in the display should be uniform. This is achieved when the pitch of the helix in the S c * phase of the liquid crystal or the liquid crystal mixture is so large as to prevent the formation of a helix in the display. Furthermore, the helix in the N * phase should be so large that there is no twist in the display during the cooling process
  • the display according to the invention is generally controlled directly or as a multiplex control (see, for example, Jean Dijon in Liquid Crystals, Application and Uses (Ed. B. Bahadur) Vol. 1, 1990, Chapter 13, pp. 305-360) or T. Harada, M. Taguchi, K. Iwasa, M. Kai SID 85 Digest, page 131 (1985), only the switching times being chosen long enough.
  • the display is preferably controlled with voltage pulses which are in the range from 0.9 ms to 2 s, particularly preferably 1.0 ms to 500 ms, in particular 10 to 300 ms.
  • Suitable components for ferroelectric liquid crystal mixtures are known to the person skilled in the art.
  • the liquid crystal mixture generally contains at least 2, preferably 5 to 30, particularly preferably 8 to 25 components.
  • the mixture is prepared by methods known per se.
  • the components of the mixture are preferably selected from the known compounds with smectic and / or nematic and / or cholesteric phases, for example of the formula (I).
  • Cyclopentylene can be replaced and / or b3) one or more H atoms can be replaced by F, CN and / or Cl and / or b4) the terminal CH 3 group by one of the following chiral
  • R 3 , R 4 , R 5 , R 6 , R 7 are the same or different a) hydrogen b) a straight-chain or branched alkyl radical (with or without asymmetric carbon atom) with 1 to 16 carbon atoms, b1) one or more not neighboring and non-terminal CH 2 -
  • M 1 , M 2 , M 3 are the same or different
  • F can be replaced, (1, 3,4) -Thiadiazol-2,5-diyl, 1, 3-dioxan-2,5-diyl, 1, 3-Dithian-2,5-diyl, 1, 3-thiazole -2,4-diyl, where one H atom can be replaced by F, Cl and / or CN, 1, 3-thiazole-2,5-diyl, one H atom replaced by F, Cl and / or CN can be thiophene-2,4-diyl, where an H atom can be replaced by F, Cl and / or CN, thiophene-2,5-diyl, where one or two H-
  • Atoms can be replaced by F, Cl and / or CN, naphthalene-2,6-diyl, naphthalene-1, 4-diyl or naphthalene-1, 5-diyl, one or more H atoms being replaced by F, Cl and / or CN can be replaced and / or one or two CH groups can be replaced by N, phenanthrene-2,7-diyl or 9,10-dihydrophenanthrene-2,7-diyl, one, two or more H- Atoms can be replaced by F and / or one or two CH groups can be replaced by N, indan-2,5-diyl, indan-1-one-2,5-diyl, benzothiazole-2,6-diyl, benzothiazole -2,5-diyl, benzoxazole-2,6-diyl, benzoxazole-2,5-diyl, benzofuran-2,5-diyl,
  • a, b, c are zero or one, with the proviso that the compound of formula (I) may not contain more than four five or more-membered ring systems.
  • the symbols and indices in the formula (I) preferably have the following meanings:
  • R 1 or R 2 are identical or different a) hydrogen, -F, -OCF 3 or -CN with the proviso that at most one of the radicals R 1 or R 2 can be hydrogen, -F, -OCF 3 or -CN b ) a straight-chain or branched alkyl radical (with or without asymmetric carbon atom) with 1 to 18 carbon atoms, where b1) one or more non-adjacent and non-terminal CH 2 -
  • Groups can be replaced by -O-, -CO-O-, -O-CO-, -O-CO-O- or -Si (CH 3 ) 2 - and / or b2) a CH 2 group by cyclopropane 1, 2-diyl, 1, 4-phenylene or trans-1, 4-cyclohexylene can be replaced and / or b3) one or more H atoms can be replaced by F and / or b4) the terminal CH 3 group by one of the following chirals
  • R 1 or R 2 are particularly preferably the same or different a) R 1 or R 2 is hydrogen b) a straight-chain or branched alkyl radical (with or without asymmetrical carbon atom) with 1 to 16 carbon atoms, where b1) one or two non-adjacent and non-terminal CH 2 -
  • Groups can be replaced by -O-, -CO-O-, -O-CO-, -O-CO-O- or -Si (CH 3 ) 2 - and / or b2) a CH 2 group by 1, 4-phenylene or trans-1, 4-cyclohexylene can be replaced and / or b3) one or more H atoms can be replaced by F and / or b4) the terminal CH 3 group by one of the following chiral
  • R 3 , R 4 , R 5 , R 6 , R 7 are particularly preferably the same or different a) hydrogen, b) a straight-chain or branched alkyl radical (with or without asymmetric carbon atom) having 1 to 14 carbon atoms, where b1) a non-terminal CH 2 group can be replaced by -O-, c) R 4 and R 5 together also - (CH 2 ) 4 - or - (CH 2 ) 5 - if they are attached to an oxirane, dioxolane, tetrahydrofuran -, tetrahydropyran, butyrolactone or valerolactone system are bound.
  • M 1 , M 2 , M 3 are preferably the same or different
  • M ⁇ M 2 , M 3 are particularly preferably the same or different
  • a ⁇ A 2 , A 3 , A 4 are preferably the same or different
  • Atoms can be replaced by F and / or CN, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F and / or CN, trans-1,4-cyclohexylene, where one or two H- Atoms can be replaced by CN and / or F, (1, 3,4) thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, 1,3-thiazole-2,4-diyl , where an H atom can be replaced by F, 1,3-thiazole-2,5-diyl, where an H atom can be replaced by F, thiophene-2,5-diyl, where one or two H atoms can be replaced by F, naphthalene-2,6-diyl, where one or two H atoms can be replaced by F and / or CN and / or one or two CH groups can be replaced by N, phenanthrene-2, 7-
  • H atoms can be replaced by F and / or one or two CH groups can be replaced by N, indane-2,5-diyl, benzothiazole-2,6-diyl or benzothiazole-2,5-d iy I.
  • a 1 , A 2 , A 3 , A 4 are particularly preferably the same or different
  • the mixture generally contains at least 2, preferably 3 to 30, particularly preferably 4 to 20 components of the formula (I).
  • Silicon compounds as described for example in EP-A 0 355 008, - mesogenic compounds with only one side chain, as for example in
  • Phenylbenzoates and biphenylbenzoates such as those from P. Keller,
  • Biphenyls as for example in EP 207.712 or Adv. Liq. Cryst. Res. Appl.
  • Suitable chiral, non-racemic dopants are: optically active phenyl benzoates, as described, for example, by P. Keller, Ferroelectrics 1984, 58, 3 and J. W. Goodby et al., Liquid Crystals and
  • WO-A 93/13093 describes optically active oxirane esters, as described, for example, in EP-A 0 292 954, optically active dioxolane ethers, as described for example in EP-A 0 351 746, optically active dioxolane esters, as described for example in EP-A 0 361 272 described - optically active tetrahydrofuran-2-carboxylic acid esters, such as in
  • EP-A 0 355 561 describes optically active 2-fluoroalkyl ethers, as for example in EP-A 0 237 007 and
  • Particularly preferred mixture components of the liquid crystal are those from groups A to M:
  • a 1 1, 4-phenylene, trans-1, 4-cyclohexylene or a single bond
  • a 2
  • Z denotes -O-CO-, -CO-O-, -S-CO-, -CO-S-, -CH 2 O-, -OCH 2 - or -CH 2 CH 2 -.
  • R is a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, -CO-, -CO-O-, -O -CO-, -O-CO-O- or -Si (CH 3 ) 2 - can be replaced, A 1 , A 2 , A 3 , A 4 the same or different
  • 1,4-phenylene where one or two H atoms can be replaced by F or CN, pyridine-2,5-diyl, where one or two H atoms can be replaced by F, pyrimidine-2,5-diyl, being one or two H atoms can be replaced by F, trans-1, 4-cyclohexylene, (1, 3,4) -
  • R ⁇ R 2 identical or different, is a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, - CO-, -CO-O-, -O-CO-, -O-CO-O- or -Si (CH 3 ) 2 - can be replaced, A 1 , A 2 , A 3 the same or different
  • 1,4-phenylene where one or two H atoms can be replaced by F, pyridine-2,5-diyl, where one or two H atoms can be replaced by F, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, trans-1, 4-cyclohexylene, where one or two H atoms can be replaced by -CN and / or -CH 3 , (1, 3,4) - thiadiazole-2 , 5-diyl, and A 1 too
  • N the number of N atoms in a six-membered ring being 0.1 or 2, a, b, c, d, e, f zero or one, provided that the sum of a + c + e 0 , 1, 2 or 3.
  • R is a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, -CO-, -CO-O-, -O -CO- or -O-CO-O- can be replaced,
  • R 2 is a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, -CO-, -CO-O-, - O-CO- or -O-CO-O- can be replaced, with the proviso that a non-oxygen-bound CH 2 group is replaced by -Si (CH 3 ) 2 -,
  • a ⁇ A 2 , A 3 the same or different
  • 1,4-phenylene where one or two H atoms can be replaced by F, trans-1,4-cyclohexylene, pyridine-2,5-diyl, where one or two H atoms can be replaced by F, pyrimidine- 2,5-diyl, where one or two H atoms can be replaced by F or (1, 3,4) -
  • R 1 , R 2 identical or different, are a straight-chain or branched alkyl radical having 1 or 3 to 16, preferably 1 or 3 to 10, carbon atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, preferably -O-, -O-CO-, -CO-O- can be replaced,
  • R 3 -CH 3 , -CF 3 or -C 2 H 5 preferably -CH 3 or -CF 3 ,
  • a 1 , A 2 the same or different
  • 1,4-phenylene trans-1,4-cyclohexylene, preferably 1,4-phenylene.
  • A is N and B is CH or A is CH and B is N, C is N and D is CH or C is CH and D is N, one or two
  • CH groups can be replaced by CF groups, R ⁇ R 2 identical or different, a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH 2 - Groups by -O-, -CO-, -CO-O-, -O-CO- or
  • R 2 is a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, -CO-, -CO-O -, -O-CO- or
  • R 1 is a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, -CO-, -CO-O-, - O-CO-, -O-CO-O- or -Si (CH 3 ) 2 - can be replaced, or the following optically active group,
  • R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are identical or different hydrogen or a straight-chain or branched alkyl radical with 1 to
  • 1,4-phenylene where one or two H atoms can be replaced by F, pyridine-2,5-diyl, where one or two H atoms can each be replaced by F, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, trans-1, 4-cyclohexylene, where one or two H atoms can be replaced by -CN and / or -CH 3 , (1, 3,4) - thiadiazole- 2,5-diyl, M 1 , M 2 the same or different
  • the asymmetric carbon atoms of the oxirane ring or rings can have the same or different R or S configuration.
  • R 1 is a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, -CO-, -CO-O-, - O-CO-, -O-CO-O- or -Si (CH 3 ) 2 - can be replaced,
  • R 2 , R 3 , R 4 are the same or different
  • the asymmetric carbon atoms of the oxirane ring can have the same or different R or S configuration.
  • R 1 is a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH 2 groups also being represented by -O-, -CO-, -CO-O-, - O-CO-, -O-CO-O- or -Si (CH 3 ) 2 - can be replaced,
  • R 2 , R 3 , R 4 are the same or different
  • Hydrogen a straight-chain or branched alkyl radical with 1 to 16 or 3 to 10 C atoms or an alkenyl radical with 2 to 16 C atoms, where R 2 and R 3 together can also be - (CH 2 ) 5 -, A 1 , A 2 , A 3 the same or different
  • 1,4-phenylene where one or two H atoms can be replaced by F, pyridine-2,5-diyl, where one or two H atoms can be replaced by F, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, trans-1, 4-cyclohexylene, where one or two H atoms can be replaced by -CN and / or -CH 3 , (1, 3,4) -
  • Asymmetric carbon atoms of the dioxolane ring can be configured the same or differently, R or S.
  • R 1 is a straight-chain or branched alkyl radical having 1 to 16 or 3 to 16 C atoms, one or more non-adjacent and non-terminal CH 2 groups being represented by -O-, -CO-, -O-CO- or -CO- Can be replaced,
  • R 2 , R 3 , R 4 are the same or different
  • Asymmetric carbon atoms of the dioxolane ring can be configured the same or differently, R or S.
  • Y -CO- (t-butyl), -CO- (adamantyl), -CO-alkyl
  • Oligoether Oligoether such as Beckopox®, Jeffamin® or
  • liquid crystal components of the formulas (I) to (XIV) are prepared by methods which are known per se and are familiar to the person skilled in the art, as described, for example, in Houben Weyl, Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart or the cited documents.
  • a particularly preferred area of application of the display according to the invention is chip or smart cards.
  • a chip card is a card, usually made of plastic and in credit card format, provided with an integrated circuit, which information NEN can store electronically, and means for information transfer between the card and an electronic reading and / or writing system.
  • a smart card is a chip card that contains means for checking / controlling access to the card. For example, this means can be an integrated circuit which controls who has the stored information about which
  • Chip and smart cards are already in widespread use, for example as “Medicards” and “cash cards” as telephone and credit cards and as ID cards for access control.
  • the FLC display according to the invention contains support plates which, because of the flexibility, are preferably made of plastic.
  • Suitable plastics are, for example, known plastics such as polyarylates, polyether sulfone, cycloolefin copolymers, polyetherimides, polycarbonate, polystyrene, polyesters, polymethyl methacrylates, and also their copolymers or blends.
  • the FLC display is embedded or applied in or on a plastic card provided with one or more electronic microchips.
  • microchips contain the program and / or memory functions which ensure the desired function of the chip card. Such chips and their manufacture are known to the person skilled in the art.
  • the chip card preferably has a format in accordance with ISO 7816 and the following.
  • the card is generally made of plastic, preferably polyvinyl chloride (PVC), acrylic butadiene styrene or copolymers (ABS).
  • PVC polyvinyl chloride
  • ABS acrylic butadiene styrene or copolymers
  • It also contains means for data exchange with an external write and / or read system, for example electrically conductive contacts or an "antenna" in the form of flat coils.
  • the plastic cards used are known and the majority are commercially available (e.g. Gemplus, http://www.gemplus.fr).
  • the chip card according to the invention is suitable, for example, as a check card, electronic ticket, telephone card, parking garage card, "electronic wallet” or for Pay TV.
  • a glass plate coated with indium tin oxide is patterned in a photolithographic process so that an electrode pattern is obtained.
  • the transparent conductor tracks of this electrode structure are used for the electrical control of the display.
  • An organic orientation layer is applied and rubbed to orient the liquid crystal mixture.
  • Two glass plates structured in this way, which form the top and bottom of the display, are joined together using an adhesive frame and filled with the mixture specified below.
  • the adhesive is cured, the cell sealed, slowly cooled to operating temperature, and assembled between a pair of polarizing films to form a finished display.
  • the external contacts of the electrodes of the display are connected to the control electronics.
  • the FLC mixture consisting of the achiral basic mixture A:
  • the S c * phase range that can be used for the display covers the temperatures from -26 ° C to 70 ° C.
  • the display has a thickness of 2 ⁇ m and can are operated with a constant working voltage of 8 V.
  • a flexible plastic film (available e.g. from Sumitomo Bakelite,
  • Product name FST 5352 thickness 100 ⁇ m, 200 ⁇ / indium tin oxide coated
  • the transparent conductor tracks of this electrode structure are used for the electrical control of the display.
  • the substrates are coated with an orientation layer and rubbed with a roller.
  • Two structured foils, which form the top and bottom of the display, are joined together using an adhesive frame and filled with the mixture named below. The adhesive is hardened, the cell sealed, by slowly cooling down
  • the FLC mixture consisting of the achiral base mixture A (see example 1) and the dopants:
  • the S c * phase range that can be used for the 'smart card' covers temperatures from -28 ° C to 73 ° C.
  • the display has a thickness of 2 ⁇ m and can be operated with a constant working voltage of 2V.
  • a flexible plastic film (available e.g. from Sumitomo Bakelite, product name FST 5352, thickness 100 ⁇ m, 200 ⁇ / indium tin oxide coated) is structured in a photolithographic process so that an electrode pattern is obtained.
  • the transparent conductor tracks of this electrode structure are used for the electrical control of the display.
  • the substrates are coated with an orientation layer and rubbed with a roller.
  • Two structured foils which form the top and bottom of the display, are joined together using an adhesive frame and filled with the mixture named below.
  • the adhesive is hardened, the cell sealed, by slowly cooling down
  • the FLC mixture consists of
  • the S c * phase range that can be used for the 'smart card' covers temperatures from -26 ° C to 77 ° C.
  • the display has a thickness of 2 ⁇ m and can be operated with a constant working voltage of 5V.
  • Q 2.1. Table 1 :
  • Table 1 shows Q (quotient of el. Field strength at 0 ° C and 40 ° C) as a function of Ps and the switching time.
  • Table 2 shows the temperature range that can be controlled with constant voltage
  • the temperature range that can be controlled with a constant 8V is only 60 ° C to 25 ° C.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Theoretical Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal Substances (AREA)
  • Liquid Crystal Display Device Control (AREA)
  • Liquid Crystal (AREA)

Abstract

Affichage à cristaux liquides ferroélectriques renfermant un mélange de cristaux liquides ferroélectriques, caractérisé en ce que l'affichage est commandé avec des impulsions de tension Sm(G)0,9 ms. L'affichage selon l'invention convient notamment pour des applications pour lesquelles la longue durée de la commutation n'est pas critique. De tels affichages peuvent être commutés avec la même tension sur un vaste spectre de température, rendant ainsi inutile un suivi de la tension en fonction de la température. Comme applications, on mentionne par exemple, de préférence, des affichages dans des cartes à puces, des panneaux électroniques d'indication de prix ou d'affichage (shelflabels), PDA (Personal Digital Assistants) et récepteurs d'appels de personnes.
EP98941322A 1997-07-18 1998-07-13 Affichage a cristaux liquides ferroelectriques a large spectre de temperature de travail Withdrawn EP0995184A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19731020 1997-07-18
DE19731020A DE19731020A1 (de) 1997-07-18 1997-07-18 Ferroelektrisches Flüssigkristalldisplay mit breitem Arbeitstemperaturbereich
PCT/EP1998/004335 WO1999004383A1 (fr) 1997-07-18 1998-07-13 Affichage a cristaux liquides ferroelectriques a large spectre de temperature de travail

Publications (1)

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EP0995184A1 true EP0995184A1 (fr) 2000-04-26

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US (1) US6549188B1 (fr)
EP (1) EP0995184A1 (fr)
JP (1) JP2001510910A (fr)
DE (1) DE19731020A1 (fr)
WO (1) WO1999004383A1 (fr)

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DE10002186B4 (de) * 2000-01-19 2018-01-18 Merck Patent Gmbh Disubstituierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen
DE10131010B4 (de) * 2001-06-27 2004-03-04 Infineon Technologies Ag Datenträger
JP2007231166A (ja) * 2006-03-01 2007-09-13 Ricoh Co Ltd 液晶素子、光路偏向素子及び画像表示装置
EP1989276A4 (fr) 2006-03-01 2011-03-02 Ricoh Co Ltd Element a cristaux liquides, element de deviation de chemin optique et dispositif d'affichage d'image
JP5261881B2 (ja) * 2006-03-01 2013-08-14 株式会社リコー 液晶素子、光路偏向素子及び画像表示装置
CN102597168B (zh) * 2009-11-04 2014-09-03 默克专利股份有限公司 用于液晶介质的化合物及其用于高频组件的用途
PL240079B1 (pl) * 2017-10-31 2022-02-14 Wojskowa Akad Tech Smektyczna mieszanina ciekłokrystaliczna domieszkowana związkami jonowymi, sposób jej otrzymywania oraz jej zastosowanie

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US4701026A (en) * 1984-06-11 1987-10-20 Seiko Epson Kabushiki Kaisha Method and circuits for driving a liquid crystal display device
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Also Published As

Publication number Publication date
WO1999004383A1 (fr) 1999-01-28
DE19731020A1 (de) 1999-01-21
JP2001510910A (ja) 2001-08-07
US6549188B1 (en) 2003-04-15

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