WO2004046805A1 - Elektrooptisches lichtsteuerelelment, elektrooptische anzeige und steuermedium - Google Patents
Elektrooptisches lichtsteuerelelment, elektrooptische anzeige und steuermedium Download PDFInfo
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- WO2004046805A1 WO2004046805A1 PCT/EP2003/012626 EP0312626W WO2004046805A1 WO 2004046805 A1 WO2004046805 A1 WO 2004046805A1 EP 0312626 W EP0312626 W EP 0312626W WO 2004046805 A1 WO2004046805 A1 WO 2004046805A1
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- 0 Cc1cnc(*c2cnc(C)nc2)cc1 Chemical compound Cc1cnc(*c2cnc(C)nc2)cc1 0.000 description 3
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Classifications
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- 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
- G02F1/13718—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 a change of the texture state of a cholesteric liquid crystal
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- 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
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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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0275—Blue phase
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
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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
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
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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
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
- C09K19/588—Heterocyclic compounds
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- 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
- G02F1/07—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 electro-optical liquids exhibiting Kerr effect
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- 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
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- 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
- G02F1/13793—Blue phases
Definitions
- the present invention relates to light control elements containing them
- the light control elements preferably use control media which have anisotropic properties at certain temperatures, such as. B. liquid crystals.
- the light control elements are operated at a temperature at which the control media are in the blue phase.
- Similar displays that use control media that are in the isotropic phase are described in DE 102 17 273.0 and in the previously unpublished patent applications DE 102 41 301.0 dated September 4, 2002, two further applications by the assignee of the present application.
- the present invention relates to an electro-optical light control element and to electro-optical displays and display systems containing such elements, such as television screens and computer monitors, and to the control media used in the light control elements.
- the light control elements according to the invention contain a mesogenic control medium which is in the blue phase when the light control elements are in operation. In addition to a good contrast and a low dependence of the contrast on the viewing angle, short switching times and a relatively low operating voltage, they are particularly distinguished by a low temperature dependence of the operating voltage.
- the present invention also relates to mesogenic media and their use as control media in such light control elements.
- the liquid crystal cells of these displays have electrodes on the substrates on the two opposite sides of the liquid crystal medium.
- the electric field is essentially vertical to the liquid crystal layer.
- the first-mentioned displays are used in combination with a TFT ("thin film transistor") control for displays with a large amount of information and high resolution.
- TFT thin film transistor
- “Desk-top” computer monitors have recently become increasingly liquid crystal displays of the IPS type (English: “in-pjane switching", for example DE 40 00 451 and EP 0 588 568) or alternatively of the VAN type (English: " yertically aligned nematic ").
- VAN displays are a modern variant of ECB displays ("electrically controlled birefringence").
- MVA displays (English: “multi domain yertically aligned"), several domains are stabilized for each driven electrode and, in addition, a special optical compensation layer is used.
- These displays like the TN displays already mentioned, use a In contrast to this, IPS displays generally use electrodes on only one substrate, that is to say on one side of the liquid crystal layer, and are therefore characterized by an essential component of the electric field parallel to the liquid crystal layer.
- Light control elements also have a pronounced temperature dependency.
- the electro-optical effect induced by the electric field in the control media in the isotropic phase is most pronounced at temperatures near the clearing point of the control media.
- the light control elements have the lowest characteristic voltages, so the lowest operating voltages are required here. With increasing temperature, the characteristic voltages and thus the operating voltage increase significantly.
- Typical temperature dependencies of the threshold voltage range from a few volts per degree to ten and more volts per degree.
- the relative temperature dependence of the characteristic voltages of the various light control elements with an isotropic control medium according to DE 102 17 273.0 and DE 102 41 301.0 can be regarded as being independent of the medium used and of the electrode structure.
- DE 102 17 273.0 describes isotropic media with some clearly varying compositions which are used in light control elements in the Isotropic phase can be operated, can be used, whereas in DE 102 41 301.0 different electrode structures are disclosed.
- the relative temperature dependence of the threshold voltage at a temperature of 1 ° above the clearing point is in the order of 50% / degree. It decreases with increasing temperature.
- Temperature of 5 ° above the clearing point is in the order of some 10% / degree.
- the alternative implementation of electronic tracking of the control voltage is relatively complex. On the one hand, it generally leads to a loss of part of the available control voltage, since this must still be sufficiently high even at the highest operating temperature. On the other hand, it involves some measurement and control effort. So the current temperature of the light control element must be determined. For displays with a larger area, it may even be necessary to determine a temperature gradient or the temperatures at several points on the display.
- the further alternative of keeping the temperature of the light control elements constant is also not easy to implement.
- the display must be heated for obvious practical reasons.
- This alternative also requires determining the temperature of the light control elements.
- Liquid crystals with a correspondingly strong chiral twist can have one or more optically isotropic mesophases. These phases appear with a corresponding cholesteric pitch, i.e. if the pitch is in the range of the wavelength of visible light, in a sufficiently large layer thickness slightly bluish. For this reason, they are referred to as blue phases (Gray and Goodby, "Smectic Liquid Crystals, Textures and Structures", Leonhard Hill, USA, Canada (1984)).
- the present invention was therefore based on the object of realizing particularly rapidly switching light control elements which use a control medium which is in an optically isotropic phase in the field-free state, with good contrast, good viewing angle dependency, low control voltages and in particular with a low temperature dependency of the control voltage to provide the necessary control media.
- These light control elements should have the smallest possible layer thickness of the control media in order to be able to be used as elements of FPDs (English: flat panel displays), such as flat screens for computers. Furthermore, they should be controllable using the simplest possible electrode configuration.
- the electro-optical light control elements according to the present invention include
- control medium a control medium
- the light control element is operated at a temperature at which the control medium is in an optically isotropic phase in the non-activated state and in that
- the mesogenic control medium is a chiral component, component (A), which consists of one or more chiral compounds and
- the mesogenic control medium has a blue phase at the temperature at which the light control element is operated or
- the mesogenic control medium at the temperature at which the light control element is operated is in the isotropic phase and -
- the electrode arrangement can generate an electric field with a significant component parallel to the surface of the mesogenic control medium.
- An electrode arrangement is preferably used which can generate an electric field with a significant component parallel to the surface of the mesogenic control medium.
- a mesogenic medium is preferably used as the control medium of the light control element.
- mesogenic media or compounds are media or compounds which have a mesophase, which are soluble in a mesophase or which induce a mesophase.
- the mesophase is a smectic, a nematic or a blue phase.
- the smectic phase or the nematic phase are preferably chiral.
- the terms “chiral nematic phase” and “cholesteric phase” are used synonymously, unless expressly stated otherwise.
- the term “blue phase” stands for each of the known blue phases and also includes several of these phases at the same time, unless expressly stated otherwise.
- phase transition into a phase which occurs at a lower temperature without an electric field is also possible.
- the determination of the phases for the characterization of the materials, particularly the control media themselves relates to the case in which there is no electric field, whereas the determination of the phases in the characterization of the light control elements takes place with the application of a corresponding voltage, usually the operating voltage, or the threshold voltage, unless expressly stated otherwise.
- the transition temperature T (*, BP) is determined in the field-free state, whereas the transition temperature T (BP, I) is determined by applying an electric field the change in the slope of the temperature dependence of the characteristic voltages of the light control elements is determined.
- the control media preferably have a blue phase, particularly preferably a blue phase and a further mesophase, preferably a cholesteric phase.
- the nematic mixture ZLI-4792 from Merck KGaA, Darmstadt, Germany is used as the preferred medium for investigating the mesogenic properties of the materials which have no mesophase.
- the mesogenic materials preferably have a clearing point of -50 ° C. or more extrapolated from 10% solution in this mixture, particularly preferably of -20 ° C. or more and very particularly preferably of 0 ° C. or more.
- the control medium contains a chiral doping component, component (A), and optionally an achiral component, component (B).
- the chiral component (A) contains one or more chiral compounds, preferably it consists of these compounds. This chiral
- Compounds have a mesogenic structure and preferably themselves have one or more mesophases, preferably at least one cholesteric phase.
- the mesogenic control medium consists only of the chiral component (A).
- the control medium contains one or more, preferably two or more, particularly preferably three, four or more chiral compounds.
- the control medium preferably contains one or more compounds which preferably have a cholesteric phase.
- the control medium can also advantageously contain one or more chiral compounds, one, several or all of which have no mesophase themselves.
- chiral compounds are preferred which have a melting point above ambient temperature, since these are easier to handle.
- connections are large HTP, ie compounds which induce a short cholesteric pitch even when using low concentrations in nematic host mixtures, is preferred.
- the mesogenic control medium consists of a chiral component (A) and an achiral component (B).
- the chiral component contains one or more, preferably two or more chiral compounds and the achiral component (B) one or more, preferably two or more, particularly preferably three, four or more achiral compounds.
- a chiral compound or a plurality of the chiral compounds of component (A) have a mesophase, preferably a cholesteric phase.
- the chiral compounds influence the physical properties of the mesogenic achiral component (B), e.g. the clearing point, the birefringence and the dielectric anisotropy, relatively little, and correspondingly large concentrations of the chiral component (A) can also be used, which enables the use of compounds with a relatively low HTP.
- the physical properties of the mesogenic, achiral component (B), e.g. the clearing point, birefringence and dielectric anisotropy are changed relatively little as long as the cholesteric pich is long enough, usually much larger than the wavelength of light.
- the chiral compound or the chiral compounds of component (A) have no mesophase.
- This embodiment is particularly preferred when the chiral component (A) has a large HTP in the achiral component (B), because then the desired low cholesteric pitch can be obtained with a small concentration of the chiral component (A) ??? which means that the physical properties of the control medium, such as the clearing point, birefringence and dielectric anisotropy, are changed only slightly compared to those of the achiral component (B).
- the cholesteric pich values are relatively small, of the order of magnitude
- the chiral component (A) induces a completely different phase in the mesogenic medium, a blue phase, the structure of which is completely different from that of the nematic and cholesteric phase.
- the physical properties, such as the clearing point, birefringence and dielectric anisotropy, of the media which contain both the chiral component (A) and the achiral component (B) are generally not accessible using the methods customary in nematic liquid crystal mixtures ,
- the chiral component (A) is replaced by an achiral component (A ') with the same concentration to determine the corresponding physical properties.
- the achiral component (A 1 ) contains the same compound or the same compounds in the same concentrations as the component (A).
- component (A) contains the
- Component (A ') is not the chiral compounds, but the corresponding racemates, i.e. an unchiral mixture of the respective two corresponding enantiomers of each of the compounds in a ratio of 1: 1.
- the blue phase occurs in the medium which contains both component (A) and component (B).
- One or more of the achiral compounds of component (B) preferably have a mesophase, preferably a smectic and / or nematic, preferably a nematic phase.
- the achiral component (B) makes up the majority of the control medium.
- the concentration of the chiral component in the control medium is preferably 0.5% to 45%, particularly preferably 1% to 35% and very particularly preferably 3% to 25%.
- the cholesteric pitch of the control medium in the cholesteric phase also called chiral nematic, can be represented in a first approximation by equation (1).
- equation (1) can be modified accordingly.
- the development of the cholesteric pitch in the form of a polynomial (2) is usually used for this.
- equation (1) is modified to equation (3).
- the temperature dependency of the HTP is usually also shown in a polynomial development (4), it often being possible to terminate after the linear element.
- HTP (T) HTP (To) + ßi ⁇ (T- T 0 ) + ß 2 ⁇ (T- T 0 ) 2 + ... (4)
- HTP HTP at temperature T
- HTP HTP at temperature To
- ßi and ß 2 constants which depend on the chiral component (A) and the achiral component (B).
- the chiral component (A) contains one or more chiral compounds with an HTP (English “helical twisting power") in the commercial, nematic host mixture MLC-6260 from Merck KGaA, Darmstadt of 10 ⁇ m "1 or more, preferably of 30 ⁇ m " 1 or more, particularly preferably of 50 ⁇ m "1 or more and very particularly preferably of 90 ⁇ m " 1 or more.
- HTP American “helical twisting power”
- the chiral component (A) contains two or more chiral compounds.
- the chiral compounds preferably all have the same sign of the HTP.
- the control medium preferably has a characteristic temperature, in a preferred embodiment a clearing point, in the range from -30 ° C. to 80 ° C., preferably up to 55 ° C.
- the light control elements according to the invention preferably contain a mesogenic medium which is in the blue phase at operating temperature. This medium is conveniently located on or under a substrate.
- the control medium is usually located between two substrates. This embodiment is preferred. If the control medium is between two substrates, at least one of these substrates is translucent.
- the translucent substrate, or the translucent substrates can, for. B. consist of glass, quartz or plastic. If a substrate is used that is not translucent, this can consist, among other things, of a metal or a semiconductor. These media can be used as such or on a support e.g. a ceramic.
- the control medium is a polymeric medium, the use of a second substrate can optionally be dispensed with. Polymer control media can even be self-supporting. In this case, no substrate is required. In this case, just as when using only flexible substrates, flexible light control elements can be implemented.
- the operating temperature of the light control element is preferably above the characteristic temperature of the control medium, usually the transition temperature of the control medium to the blue phase, in which Usually in the range from 0.1 ° to 50 ° above this temperature, preferably in the range from 0.1 ° to 10 ° above this temperature and particularly preferably in the range from 0.1 ° to 5 ° above this temperature.
- the operating temperature is preferably in the range from the transition temperature of the control medium to the blue phase to the transition temperature of the control medium to the isotropic phase, the clearing point.
- the light control elements can also be operated at temperatures at which the control medium is in the isotropic phase. Then, however, the temperature dependence of the operating voltage increases, which is usually undesirable.
- the operating temperature range of the light control elements according to the invention preferably extends at least over a temperature range of 5 ° or more, preferably 20 ° or more, preferably of
- the operating temperature range of the light control elements according to the invention preferably extends at least from 10 ° C. or less to 50 ° C. or more, preferably at least from 0 ° C. or less to 60 ° C. or more, particularly preferably at least from -20 ° C. or less to 80 ° C or more, most preferably at least from -30 ° C or less to 100 ° C or more, and most preferably at least from -40 ° C or less to 120 ° C or more.
- the operating temperature range of the light control elements according to the invention extends relative to the characteristic temperature of the control medium at least up to 50 ° C. or more above the characteristic temperature, particularly preferably at least -5 ° C. or less below the characteristic temperature up to 60 ° C or more above the characteristic temperature and very particularly preferably at least from -10 ° C below the characteristic temperature or less to 80 ° C or more above the characteristic temperature.
- a voltage is applied, an orientation is induced in the optically isotropic phase in the mesogenic medium, which leads to an optical delay which can be visualized in a known manner, for example and preferably between crossed polarizers.
- An inhomogeneous electric field is preferably used.
- the light control elements according to the invention contain at least one element for polarizing the light. In addition, they preferably contain a further optical element. This further optical element is either a second element for polarizing the light, a reflector or a transflector.
- the optical elements are arranged such that the light passes through at least one polarizing element at least once when it passes through the mesogenic medium of the light control element both before it enters the mesogenic medium and after it exits the mesogenic medium.
- the mesogenic medium is located between two polarizers, that is to say a polarizer and an analyzer.
- Two linear polarizers are preferably used.
- the absorption axes of the polarizers are preferably crossed and preferably form an angle of 90 °.
- the light control element according to the invention optionally contains one or more birefringent layers. It preferably contains one ⁇ / 4 layer or several ⁇ / 4 layers, preferably one ⁇ / 4 layer.
- the optical delay of the ⁇ / 4 layer is preferably approximately 140 nm.
- the layer thickness (d) of the mesogenic control medium is preferably 0.1 ⁇ m to 5,000 ⁇ m (ie 5 mm), particularly preferably 0.5 ⁇ m to 1,000 ⁇ m (ie 1 mm), particularly preferably 1.0 ⁇ m to 100 ⁇ m and very particularly preferably 1.5 ⁇ m, preferably 3.0 ⁇ m, to 30 ⁇ m and in particular 2.0 ⁇ m, preferably 3.5 ⁇ m, to 20 ⁇ m.
- the layer thickness of the mesogenic control mediums preferably 0.5 ⁇ m to 50 ⁇ m, particularly preferably 1.0 ⁇ m to 20 ⁇ m and very particularly preferably 1.0 ⁇ m to 8.0 ⁇ m.
- the present invention also relates to electro-optical displays which contain one or more light control elements according to the invention. These electro-optical displays are preferably controlled by means of an active matrix.
- the present invention further relates to electro-optical display systems containing one or more electro-optical displays according to the invention.
- These electro-optical display systems are preferably used to display information, among other things, preferably as a television screen or as a computer monitor.
- the information to be displayed is preferably digital signals or video signals.
- the light control element according to the invention can additionally contain one or more other conventional optical elements such as birefringent layers (e.g. compensation layers), diffuser layers, and elements for increasing the brightness and / or the luminous efficiency and / or the viewing angle dependency, this list not being exhaustive.
- birefringent layers e.g. compensation layers
- diffuser layers e.g., diffuser layers
- the light control elements according to the invention are characterized by a good contrast, which is strong and almost predominantly from that
- the polarizers used depends. For comparison with conventional TN cells, TN cells with an optical delay of 0.50 ⁇ m, positive contrast and the absorption axis of the polarizers perpendicular to the preferred orientation of the nematic liquid crystals on the adjacent substrate, which do not contain chiral liquid crystals, are used here.
- the contrast of the light control elements according to the invention depends, among other things, in particular on the shape, type and structure of the electrodes used. If the same polarizers are used in the light control elements according to the invention and in these conventional TN cells, the contrast of the light control elements according to the invention is generally 20% or more, in part, especially at observation angles that deviate greatly from the normal of the display surface, 40% or more larger than the contrast of the TN cells.
- an isocontrast curve of a given contrast ratio in the light control elements according to the invention generally includes an angular range which is more than twice as large, often even more than three times as large as the corresponding isocontrast curve for the same contrast ratio in the TN display. .
- the switching times of the light control elements according to the invention are very short. As a rule, they are values of 5 ms or less, preferably 1 ms or less, particularly preferably 0.5 ms or less and very particularly preferably 0.1 ms or less.
- the electro-optical characteristic was characterized by characteristic voltages.
- the voltages at which 10%, 50% or 90% relative contrast is achieved were used for this purpose.
- Voltages (short V ⁇ 0 , V 5 o and V 90 ) are also as threshold, Mittgrautial Saturation voltage.
- V 70 the voltage at which 70% relative contrast is reached was generally determined.
- Electro-optical displays according to the present invention contain one or more light control elements according to the invention. These are in a preferred embodiment controlled by an active matrix.
- the light control elements according to the invention are actuated in the so-called “field sequential mode”.
- the switching elements are illuminated in succession with differently colored light in synchronism with the actuation.
- a color wheel for example, Strobe lamps or flash lamps are used.
- Electro-optical displays according to the present invention can contain a color filter for displaying colored images.
- This color filter expediently consists of a mosaic of filter elements of different colors.
- An element of the color filter mosaic of a color is typically associated with each electro-optical switching element.
- the light control elements according to the invention contain an electrode structure which generates an electric field with a significant component parallel to the layer of the mesogenic medium.
- This electrode structure can be designed in the form of interdigital electrodes. It can be designed in the form of combs or ladders. Designs in the form of superimposed "H” s and double “T” s or Ts are also advantageous.
- the electrode structure is advantageously located on only one side of the mesogenic medium, if at least one substrate is used, preferably between this and the mesogenic medium.
- the electrode structure is preferably present in at least two different planes, both of which are located on one side of the mesogenic control medium. This applies in particular if the electrode structure contains overlapping partial structures.
- These substructures are advantageously separated from one another by a dielectric layer. If the substructures are on the opposite sides of an insulation layer, a "lay out" can be selected which allows capacitors to be produced. This is particularly advantageous when controlling displays by means of an active matrix.
- Such an active matrix Displays use a matrix of control elements assigned to the individual light control elements with a non-linear current-voltage characteristic, such as, for. B. TFTs or MIM (English: “metal insulator metal”) diodes.
- the structure of light control elements with a mesogenic control material in an optically isotropic phase is described in principle in DE 102 172 73.0.
- the structure of the light control elements according to the invention is briefly described here.
- the switching element contains the control medium between the inner surfaces of the substrates. On the inner surface of the one substrate there is that of the electrode structure with at least two electrodes which can be acted upon with different potentials.
- the electrodes can be made of transparent material, such as. B. Indium Tin Oxide (ITO). In this case, it may be advantageous and possibly necessary to cover a part or parts of the light control element using a black mask. This allows areas where the electric field is not effective to shield and thus improve the contrast.
- ITO Indium Tin Oxide
- the electrodes can also be made of opaque
- Material usually made of metal, e.g. made of chrome, aluminum, tantalum, copper, silver or gold, preferably made of chrome. In this case, the use of a separate black mask may not be necessary.
- the electric field used is preferably an inhomogeneous field.
- the electrodes preferably have a spacing from one another in the range from 0.5 ⁇ m to 100 ⁇ m, preferably in the range from 1 ⁇ m to 20 ⁇ m, particularly preferably in the range from 1 ⁇ m to 15 ⁇ m is particularly preferably in the range from 2 ⁇ m to 12 ⁇ m and most preferably in the range from 2 ⁇ m, preferably from 3 ⁇ m to 11 ⁇ m.
- control voltage decreases as the electrode distance decreases. At the same time, however, the opening ratio and thus the
- Transmission and with a given lighting also the brightness of the display.
- an electrode spacing that is 8 ⁇ m or more, particularly preferably 10 ⁇ m or more and very particularly preferably 12 ⁇ m or more is preferably used.
- the distance between the electrodes is preferably 19 ⁇ m or less, particularly preferably 15 ⁇ m or less, very particularly preferably 10 ⁇ m or less and particularly preferably 9 ⁇ m or less.
- the width of the electrodes in the direction of the neighboring electrodes, to which different potentials can be applied, is less critical than the distance between the electrodes in this direction. It has almost no influence on the characteristic voltages of the light control elements. However, as the width of the electrodes increases
- Opening ratio of the light control element is smaller and the brightness decreases, especially if the electrodes are made of opaque material.
- the electrodes preferably have a width in the range from 0.5 ⁇ m to 30 ⁇ m, preferably in the range from 0.5 ⁇ m to 20 ⁇ m, particularly preferably in the range from 0.7 ⁇ m to 19 ⁇ m, very particularly preferably in the range from 1 ⁇ m to 9 ⁇ m and most preferably in the range from 1.5 ⁇ m to 6 ⁇ m.
- the mesogenic media according to the present invention preferably have a blue phase.
- media can also be used in which the temperature range of the blue phase is so narrow that there is practically a transition from the crystalline phase, from the smectic phase or from the nematic phase to the isotropic phase.
- the characteristic temperature or the clearing point of the mesogenic media which preferably have a blue phase, is preferably in the range from -20 ° C. to 80 ° C., preferably from -30 ° C. to 80 ° C.
- the characteristic temperature or the clearing point is 60 ° C. or less, particularly preferably it is in the range from 0 ° C. to 60 ° C., preferably in
- the characteristic temperature in a preferred embodiment the clearing point, is preferably in the range from 10 ° C. to 70 ° C. and particularly preferably in the range from 30 ° C. to 60 ° C.
- the blue phase is preferably stable to -10 ° C, particularly preferably to -30 ° C and very particularly preferably to -40 ° C.
- the optical anisotropy of the medium or the achiral component (B) of the medium at a temperature of 4 ° below the characteristic temperature or the clearing point, the medium or the component (B) is preferably 0.070 or more, preferably 0.080 or more, particularly preferably 0.090 or more and very particularly preferably 0.100 or more.
- a higher control voltage is necessary than when using media with a larger optical anisotropy.
- media with an achiral component can also be used which have a smaller optical anisotropy than 0.070.
- the achiral component (B) of the mesogenic media according to the invention preferably has a birefringence ( ⁇ n) of 0.100 or more, particularly preferably of, in the nematic phase at a temperature of 4 degrees below the clearing point
- the concentration of the chiral component (A) is 20% or less, preferably 10% or less and very particularly preferably 7% or less of the mesogenic medium.
- the value of the birefringence of component (B) is virtually unlimited for the application according to the invention. In practice, however, it is usually 0.500 or less and usually 0.450 or less.
- the value of the birefringence of the media according to the invention is measured here in the nematic phase at a temperature of 4 ° below the clearing point.
- the achiral component of the control medium (component (B)) is not stably nematic at this temperature or at least up to this temperature subcoolable in the nematic phase, then, just as with individual substances and premixes, the birefringence of a mixture of the medium and the nematic becomes Mixture ZLI-4792 from Merck KGaA determined at 20 ° C and extrapolated from the change compared to mixture ZLI-4792 to the value of the pure medium. 10% of the medium and 90% of the mixture ZLl-4792 are used.
- solubility of the medium is not sufficient, a concentration of 5% is used and if the solubility is still not sufficient, the nematic mixture MLC-6828 from Merck KGaA is used as the host mixture, as described further below, and if necessary also here Concentration decreased from 10% to 5%.
- the process of extrapolating the values from the host mixture is used for all corresponding properties of the media, provided that these cannot be examined in the nematic phase at the corresponding temperature.
- Component (B) of the mesogenic media according to the present invention preferably has a dipole element of 4 debye or more, particularly preferably 6 debye or more and particularly preferably 8 debye or more.
- Both mesogenic control media whose component (B) have a positive dielectric anisotropy ( ⁇ ) in the mesophase and those whose component (B) have a negative dielectric anisotropy in the mesophase can be used for the light control elements according to the present invention.
- component (B) of the mesogenic control media has a positive dielectric anisotropy, this has a value of preferably 15 or more, particularly preferably 30 or more and at 1 kHz and a temperature of 4 ° below the clearing point, preferably in the nematic phase most preferably 45 or more. If component (B.) of the medium has no nematic phase or if it is not in the nematic phase at a temperature of 4 ° below the clearing point, its dielectric anisotropy, like birefringence, is determined by extrapolating the values of a corresponding host mixture determined.
- component (B) of the mesogenic control medium has a negative dielectric anisotropy, this is preferably -5 or less, particularly preferably -7 or less and very particularly preferably -10 or less.
- the nematic mixture ZLI-3086 from Merck KGaA is used as the host mixture, if necessary.
- Control media with a component (B) of positive dielectric anisotropy are particularly preferred.
- the control media according to the invention preferably have a characteristic voltage V 10 in the range from 5 V to 150 V, preferably from 15 V to 110 V, particularly preferably from 20 V to 90 V and in the light control elements according to the invention at a temperature of 2 degrees above the characteristic temperature very particularly preferably from 30 V to 80 V.
- the characteristic voltages are given in this application for cells with a width of the electrodes of 10 ⁇ m and an electrode spacing of 10 ⁇ m, unless expressly stated otherwise.
- the control media according to the invention particularly preferably have a characteristic voltage V-io in the light control elements according to the invention at a temperature of 2 degrees above the characteristic temperature 105 V or less, preferably 95 V or less, particularly preferably 75 V or less and very particularly preferably 50 V or less.
- control media according to the invention have a characteristic voltage V-io in the range from 2 V, preferably from 5 V to 110 V, particularly preferably from 10, in the light control elements according to the invention at a temperature of 2 degrees above the characteristic temperature V to 90 V and very particularly preferably from 10 V to 80 V.
- control media according to the invention have a characteristic voltage V- in the range from 2 V to 100 V, preferably from 3 V to 50 V, particularly preferably in the light control elements according to the invention at a temperature of 2 degrees above the characteristic temperature from 4 V to 30 V, very particularly preferably from 5 V to 20 V and most preferably from 5 V or 7 V to 15 V.
- Tc h ar. a characteristic temperature
- the characteristic temperature if the characteristic voltage as a function of temperature passes through a minimum, the temperature of this minimum is called the characteristic temperature
- the control medium has one or more blue phases, the temperature of the transition to the blue phase becomes when several blues occur
- phases the temperature of the transition to the blue phase that occurs first with increasing temperature referred to as the characteristic temperature
- the characteristic temperature if the characteristic voltage as a function of temperature has no minimum and the control medium also no blue Phase, the temperature of the transition to the isotropic phase is referred to as the characteristic temperature.
- the control media according to the invention preferably have a low temperature dependence of the characteristic voltages (Vx), for example V 10 , V 50 , V 70 and V 90, in the light control elements according to the invention.
- the temperature dependence (dV ⁇ / dT) of the characteristic voltages (V x ) is preferably described by their relative values (dV * ⁇ / dT). For this purpose, it is related to the respective characteristic voltage at a reference temperature.
- the reference temperature (T. R.) The temperature is 2 degrees above the characteristic temperature of the respective control medium.
- Vx the voltage at which X% relative contrast is reached
- T the temperature
- Tre f the reference temperature
- T re f. T cha r. + 2 ° (see text)
- the relative temperature dependency of the characteristic voltages is preferably specified over a certain temperature range, starting below to above the desired operating temperature.
- the operating temperature is preferably in a range from 0.5 ° to 60 °, particularly preferably from 1 ° to 50 ° and very particularly preferably from 1 ° to 30 ° above the characteristic temperature of the control medium in the cell.
- the temperature dependency in this application is over a range from (approx.) One degree below to (approx.) One degree above a temperature of two (approx.) Degrees above the characteristic
- Temperature of the control medium specified.
- the temperature dependency is given as the quotient of the difference between the voltage values at the extreme temperatures (end temperatures or limit temperatures) and the difference between these temperatures and assigned to the mean value of these temperatures, unless explicitly stated otherwise.
- the amount and preferably the value of the temperature dependence of the characteristic voltages, preferably of V 70 , in this temperature range is preferably in the range from 0% / degree to 30% / degree, preferably in the range from 0% / degree to 23% / degree, preferably up to 22% / degree, preferably up to 20% / degree, particularly preferably in the range from 0% / degree to 15% / degree, preferably up to 12% / degree and very particularly preferably from 0% / degree to 7% / degree.
- the light control elements according to the invention preferably have a low temperature dependence over a wide range of operating temperatures.
- the limits mentioned apply particularly preferably to the temperature dependency over a temperature range of +/- 1 ° or more around the operating temperature in the range of the operating temperatures selected from the range from 2 ° above the characteristic temperature of the control medium to 10 ° above the characteristic temperature, particularly preferably above a temperature range of +/- 4 ° around the temperature of 5 ° above the characteristic temperature, particularly preferably over a temperature range of +/- 1 ° or more around the operating temperature in the range of operating temperatures selected from the range of 2 ° above the characteristic temperature up to 20 ° above the characteristic temperature, very particularly preferably over a temperature range of +/- 4 °, preferably +/- 9 ° around the temperature of 10 ° above the characteristic temperature.
- control media used in the light control elements according to the invention preferably have a blue phase which extends over a temperature range with a width of 5 degrees or more, preferably of 10 degrees or more, particularly preferably from 20 degrees or more and very particularly preferably from 30 degrees or more.
- control media used in the light control elements according to the invention preferably have a blue phase which extends over a temperature range with a width of 15 degrees or more, particularly preferably 30 degrees or more and very particularly preferably 40 degrees or extends more.
- the control media preferably have an operating temperature range, preferably a blue phase in the temperature range from 20 ° C. or less to 35 ° C. or more, particularly preferably in the temperature range from 10 ° C. or less to 50 ° C. or more, particularly preferably in the temperature range from 0 ° C or less to 60 ° C or more, and most preferably in the temperature range from -30 ° C or less to 80 ° C or more.
- the width of the temperature range of the blue phase is determined as follows, unless expressly stated otherwise.
- the HTP of the individual compounds of the chiral component (A) or of the entire chiral component (A) is first determined in the commercially available liquid crystal mixture MLC-6828 from Merck KGaA.
- a mixture of the chiral component (A) in the (especially developed for this purpose) achiral liquid crystal mixture AM-3 is then produced to check the occurrence of a blue phase.
- the composition and properties of this mixture are given in Example 4.
- the concentration of component (A) in the achiral mixture is chosen such that the cholesteric pitch of the resulting mixture is in the range from 180 nm to 800 nm, preferably in the range from 400 nm to 600 nm and particularly preferably at 550 nm.
- a drop of the mixture thus obtained is covered on a slide with a glass plate and examined under the microscope. At a layer thickness of approx. 100 ⁇ m or more, the blue phase can be observed directly (see also Gray and Goodby).
- the mixture of the control medium to be examined can then be produced.
- the chiral component (A) is dissolved in the achiral component (B) in the desired concentration.
- the cholesteric pitch can optionally be increased until the blue phase is accessible for observation under the microscope. The following three options are available for this, which are specified in the order of their preference:
- the concentration of component (A) is reduced, e.g. by adding component (B) until the value of the cholesteric pitch given above in connection with the method described with the reference mixture AM-3 is reached;
- the compensation of the HTP of component (A) is carried out by using one or more chiral compounds with the opposite sign of HTP to component (A) until the desired pitch and
- Component (A) corresponding enantiomers to compensate for the HTP of component (A) in the concentration which leads to the desired pitch being reached.
- the mixture of component (A) and (B) is filled as a control medium into a cell with a layer thickness of 20 ⁇ m or less, preferably about 10 ⁇ m, and examined for its electro-optical properties.
- phase behavior of the control medium is then examined in the electro-optical test cell. For this, the
- the occurrence of the blue phase in the light control element can be recognized by the onset of the optical isotropy with increasing temperature.
- the electro-optical effect occurs at the transition temperature at which the conversion into an optically isotropic phase takes place, similar to that described in DE 102 17 273.0.
- the media according to the present invention are then in the blue phase and not in the isotropic phase, like the media described in DE 102 17 273.0.
- the electro-optical effect in the light control elements according to the invention is characterized as follows. The cells are (completely) dark with crossed polarizers. This is especially true when the cholesteric pitch is much smaller than the wavelength of the light used.
- the contrast of the electro-optical effect according to the invention has virtually no viewing angle dependency and the effect shows no bistability.
- the characteristic voltages generally increase slightly as the temperature rises. This effect can be observed over the entire area of the blue phase. Even after the transition temperature from the blue phase to the isotropic phase has been exceeded, the electro-optical effect can be observed.
- the operating temperature range of the light control elements according to the invention is therefore generally greater than the range in which the blue phase occurs in the control media. At temperatures above the phase transition from the blue phase to the isotropic phase, however, the gradient of the increase in the characteristic voltages with the temperature is significantly larger than in the blue phase.
- the transition temperature from the blue to the isotropic phase can be obtained by interpolation from the respective (often almost linear) courses of the characteristic voltages with the temperature below or above this transition temperature.
- the temperature range over which the blue phase occurs in the control medium can also be confirmed by DSC (English “differential scanning calorimetry”).
- DSC Differential scanning calorimetry
- the width of the blue phase is defined as follows in the present application.
- the temperature at the upper end of the phase range is defined as the temperature at which the characteristic voltage assumes twice the value of the minimum of the characteristic voltage.
- the temperature at the lower end of the phase range is the temperature at which the characteristic voltage also assumes twice the value of the minimum of the characteristic voltage. However, if this value is not reached at temperatures below the temperature of the minimum, the temperature at which the electro-optical effect first occurs with increasing temperature is defined as the temperature of the lower end of the phase range.
- the electro-optical effect preferably shows when viewed from the preferred viewing angle, preferably over a viewing angle range that extends horizontally and vertically up to 30 ° or more, preferably up to 40 ° or more, particularly preferably up to 45 ° or more and very particularly up to 60 ° or more, a contrast ratio of 5: 1 or more, preferably 10: 1 or more and very particularly preferably 15: 1 or more.
- the electro-optical effect preferably shows a switching time of 15 ms or less, preferably 10 ms or less, particularly preferably 5 ms or less and very particularly preferably 3 ms or less.
- the switching times are determined under the following conditions, unless explicitly stated otherwise.
- ⁇ on the value of the square-wave voltage is increased from V 0 to V-ioo of the switching element and the time that elapses for the change in the transmission or the relative contrast from 10% to 90% is determined.
- the switch-off time ( ⁇ 0ff ) is specified for switching from 90% to 10% relative contrast when the voltage is reduced from V-ioo to Vo.
- the clearing point of the control medium in the cell differs from that in bulk, the characteristic voltages in the control media which do not have a blue phase and in which the characteristic voltages do not go through a minimum with increasing temperature, the temperature becomes the clear point in related to the cell.
- the mesogenic control medium does not have a clear clearing point when determined in a capillary in the clearing point measuring device (Mettler), but rather a relatively wide clearing range, which is typically a few degrees wide, here, in deviation from the usual definition , not the beginning of the clarification, but the end of the clarification area referred to as the clarification point.
- the mesogenic media according to the present invention preferably consist of two to 40 compounds, particularly preferably five to 30 compounds and very particularly preferably seven to 25 compounds.
- the chiral compounds of the chiral component (A) preferably have a high HTP. They are also called chiral dopants because they are usually added to mesogenic base mixtures in relatively low concentrations. They preferably have good solubility in the achiral component (B). They affect the mesogenic or liquid crystalline properties of the mesogenic
- the cholesteric pitch has small values that are much smaller than the wavelength of the light.
- the cholesteric pitch is on the order of the wavelength of light, they induce a blue phase, with a completely different structure than that of the cholesteric phase.
- two or more chiral compounds are used, they can have the same or the opposite direction of rotation and the same or opposite temperature dependence of the twist.
- Chiral compounds with an HTP in the commercial liquid crystal mixture MLC-6828 from Merck KGaA are particularly preferred of 20 ⁇ m "1 or more, in particular of 40 ⁇ m " 1 or more, particularly preferably of 70 ⁇ m "1 or more.
- the chiral component (A) consists of two or more chiral compounds, all of which have the same sign of the HTP.
- the temperature dependence of the HTP of the individual connections can be large or small.
- the temperature dependence of the pitch of the medium can be compensated for by mixing compounds with different temperature dependencies of the HTP in appropriate ratios.
- optically active component ??? a large number of commercially available chiral dopants are available to the person skilled in the art
- Particularly suitable dopants are compounds which have one or more chiral radicals and one or more mesogenic groups, or one or more aromatic or alicyclic groups which form a mesogenic group with the chiral radical.
- Suitable chiral radicals are, for example, chiral branched hydrocarbon radicals, chiral ethanediols, binaphthols or dioxolanes, furthermore mono- or multi-bonded chiral radicals selected from the group comprising sugar derivatives, sugar alcohols, sugar acids, lactic acids, chiral substituted glycols, steroid derivatives, terpene acids or derivatives of amino derivatives, amino acids few, preferably 1-5, amino acids.
- Preferred chiral residues are sugar derivatives such as glucose, mannose, galactose, fructose, arabinose, dextrose; Sugar alcohols such as, for example, sorbitol, mannitol, iditol, galactitol or their anhydro derivatives, in particular dianhydrohexites such as dianhydrosorbide (1: 4: 3,6-dianhydro-D-sorbide, isosorbide), dianhydromannite (isosorbitol) or dianhydroidite (isoiditol); Sugar acids such as, for example, gluconic acid, gulonic acid, ketogulonic acid; chiral substituted glycol residues such as mono- or oligoethylene or propylene glycol, in which one or more CH 2 groups are substituted by alkyl or alkoxy; Amino acids such as alanine, valine, phenylglycine or phenylalanine, or sequences of 1 to 5 of these
- Suitable chiral radicals and mesogenic chiral compounds are described, for example, in DE 34 25 503, DE 35 34 777, DE 35 34 778, DE 35 34 779 and DE 35 34 780, DE 43 42 280, EP 01 038 941 and DE 19541 820.
- Dopants are particularly preferably selected from the group comprising compounds of the following formulas A-1 to A-III.
- R a i ⁇ and R a i2 ⁇ independently of one another, alkyl, oxaalkyl or alkenyl with 2 to 9, preferably up to 7 C atoms and R a11 also methyl or alkoxy with I to 9 C atoms, preferably both alkyl, preferably n-alkyl,
- R a21 and R a22 independently of one another, alkyl or alkoxy having 1 to 9, preferably up to 7 carbon atoms, oxaalkyl, alkenyl or alkenyloxy having 2 to 9, preferably up to 7 carbon atoms, preferably R a21 R a22 , preferably alkyl, preferably n-alkyl,
- R a31 and R a32 independently of one another, alkyl, oxaalkyl or alkenyl with 2 to 9, preferably up to 7 C atoms and R a11 also methyl or alkoxy with I to 9 C atoms, preferably both alkyl, preferably n-alkyl,
- Dopants are particularly preferably selected from the group comprising compounds of the following formulas.
- hydrobenzoin Diphenylethanediol (hydrobenzoin), especially mesogenic hydrobenzoin derivatives of the following formula A-V
- B and C are each independently 1, 4-phenylene, which can also be mono-, di- or trisubstituted by L, or 1, 4-cyclohexylene,
- R ° alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl or
- the compounds of the formula A-IV are described in WO 98/00 428.
- the compounds of formula A-V are described in GB-A-2 328 207.
- Very particularly preferred dopants are chiral binaphthyl derivatives as described in WO 02/94 805, chiral binaphthol acetal derivatives as described in WO 02/34 739, chiral TADDOL derivatives as described in WO 02/06 265, and chiral dopants with at least one fluorinated bridging group and a terminal or central chiral group as described in WO 02/06 196 and WO 02/06 195.
- X 1 , X 2 , Y 1 and Y 2 each independently of one another, F, Cl, Br, I, CN, SCN, SF 5 , straight-chain or branched alkyl having 1 to 25 C atoms, soft one or more times by F, Cl, Br, I or CN can be substituted, in which also one or more non-adjacent CH 2 groups, in each case independently of one another, by -O-, -S-, -NH-, NR ° -, -CO-, -COO -, -OCO-, -OCOO-,
- x 1 and x 2 each independently, 0, 1, or 2
- y 1 and. each independently, 0, 1, 2, 3, or 4,
- B 1 and B 2 are an aromatic or a partially or completely saturated aliphatic six-membered ring, in which one or more CH groups are represented by N -
- W 1 and W 2 each independently of one another, -Z 1 -A 1 - (Z 2 -A 2 ) m -R, one of the two alternatively also R 1 or A 3 , but not both simultaneously H, or
- U and U 2 each independently of one another, CH 2 , O, S, CO, or CS,
- V 1 and V 2 each independently of one another, (CH 2 ) n , in which one to four non-adjacent CH 2 groups can be replaced by O and / or S, and one of V 1 and V 2 , and in the case that
- Z 1 and Z 2 each independently of one another, -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR ° -CO-, -0-CH 2 -, -CH2-O-, -S-CH 2 -, -CH 2 -S-, -CF2-O-, -O-CF2-, -CF 2 -S-, -S-CF 2 -, -CH2-CH2-, -CF 2 -CH2-, -CH2-CF2-, -CH2-CF2-, -CH2-CF2-, -CH2-CF2-, -CH2-CF2-, -CH2-CF2-,
- a 1 , A 2 and A 3 each independently, 1, 4-phenylene, in which one or two non-adjacent CH groups can be replaced by N, 1, 4-cyclohexylene, in which one or two non-adjacent CH 2 groups can be replaced by O and / or S, 1,3-dioxolane-4,5-diyl, 1,4-cyclohexenylene, 1,4-bicyclo- (2,2,2) -octylene, piperidine-1,4- diyl, haphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1, 2,3,4-tetrahydronaphthalene-2,6-diyli, where each of these groups can be substituted one or more times by L, and also A 1 a
- halogen atom preferably F, CN, N0 2l alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl or alkoxycarbonyloxy with 1-7 C atoms, in which one or more H atoms can be replaced by F or Cl,
- n in each case independently 0, 1, 2 or 3 and
- R and R each independently of one another, H, F, Cl, Br, I, CN, SCN, SF 5 , straight-chain or branched alkyl with 1 or 3 to 25 C-
- B, R ° and Z ° have the meaning given for formula A-IV and b is 0, 1 or 2, and Z ° in particular denotes -OCO- or a single bond.
- R has the meaning given for formula A-IV, X is H, F Cl, CN or R °, preferably F.
- the dopants of the above formulas A-IV, AV, and A-VI show good solubility in the achiral Component, and induce a cholesteric structure with high twist and low temperature dependence of the helical pitch.
- media according to the invention with favorable properties can be obtained in small amounts, which are particularly suitable for use in light control elements in which the control medium is controlled in the optically isotropic phase.
- the achiral component (B) of the mesogenic media according to the invention with positive dielectric anisotropy according to the present invention preferably contains
- B-A a component consisting of one or more compounds with a very strongly positive dielectric anisotropy of 30 or more
- B-B a component consisting of one or more compounds with a highly positive dielectric anisotropy of 10 to ⁇ 30,
- component (B-C) consisting of one or more compounds with a moderately positive dielectric anisotropy of> 1.5 to ⁇ 10,
- a component (B-D) consisting of one or more dielectric neutral connections with a dielectric
- a component (B-E) consisting of one or more compounds with a negative dielectric anisotropy of less than -1.5.
- Component (BA) of component (B) of these media preferably contains one or more compounds of the formula I and particularly preferably consists predominantly and very particularly preferably almost completely of one or more compounds selected from the compounds of the formulas I and II,
- R 1 is alkyl with 1 to 7 carbon atoms or oxaalkyl with 2 to 7 carbon atoms, in each case preferably with 2 to 5 carbon atoms, preferably alkyl,
- the compounds of the formula I preferably having three or more, more preferably four or more fluorine atoms on the phenyl rings, but preferably not more than two F atoms per phenyl ring, particularly preferably Y. ⁇ 11, ⁇ Y / 12 and Y - 13 F and preferably Z 12 means -COO
- n 2 represents 0 or 1.
- component (B) of the media contains one or more compounds of the formula I and preferably consist predominantly and particularly preferably almost completely of one or more compounds of the formula I.
- the compounds of the formula I are preferably selected from the group of the compounds 1-1 and I-2
- R 1 is alkyl having 1 to 7, preferably 1 to 5, preferably to 3
- the media according to the invention particularly preferably comprise one or more compounds of the formula I, preferably of the formula 1-1 and / or of the formula I-2, in which X 1 is CF 3 .
- the compounds of the formula II are preferably selected from the group of the compounds H-1 to li-7
- R 2 is alkyl or alkoxy having 1 to 7 carbon atoms, alkenyl,
- the media according to the invention preferably contain one or more compounds selected from the group of the compounds of the formulas 111 to II-5, preferably compounds in which Z 22 denotes -CO-O- or -CF 2 -0-.
- component (BA) of component (B) of the media according to the invention preferably contains one or more compounds of the formula II and particularly preferably consists predominantly and very particularly preferably almost completely of one or more compounds of the formula II.
- Both the mesogenic control media which have a positive dielectric anisotropy ( ⁇ ) in the mesophase and those which have a negative dielectric anisotropy can be used for the light control elements according to the present invention.
- Mesogenic control media are preferably used which have a positive dielectric anisotropy ( ⁇ ) in the mesophase. If the mesogenic control media have a positive dielectric anisotropy, the achiral component (B) of these media at 1 kHz and a temperature of 4 ° below the clearing point, preferably in the nematic phase, preferably has a value of ⁇ of 40 or more, particularly preferred 50 or more and especially 60 or more.
- component (B) of the mesogenic media according to the present invention with positive dielectric anisotropy contains one or more components selected from the group of components (BB) to (BD), preferably selected from the group of components (BB) and (BD), particularly preferably component (BB).
- Component (B) of the mesogenic media according to the present invention with positive dielectric anisotropy preferably contains
- Component (B) of the mesogenic media according to the present invention with positive dielectric anisotropy preferably contains
- 0% to 30% preferably 0% to 20%, particularly preferably 3% to 15% of one or more compounds of the formula II-6 and / or - 0% to 35% preferably 0% to 30%, particularly preferably 3% to 12 % of one or more compounds of the formula II-7.
- the component (BE) of these media preferably contains one or more compounds.
- the mesogenic media with negative dielectric anisotropy according to the present invention preferably contain
- BA 1 A component (BA 1 ) consisting of one or more
- B-B ' consisting of one or more compounds with a moderately negative dielectric anisotropy of -1.5 to ⁇ -5,
- component (B-C) consisting of one or more dielectrically neutral compounds with a dielectric anisotropy of -1, 5 to +1, 5 and
- a component (B-D ) consisting of one or more compounds with a positive dielectric anisotropy of more than 1.5.
- the mesogenic media according to the present application preferably contain
- the mesogenic medium according to the present invention can further additives, for example stabilizers or dichroic dyes, in the usual Contain concentrations.
- the total concentration of these further constituents is in the range from 0% to 0%, preferably in the range from 0.1% to 6%, based on the total mixture.
- the concentrations of the individual of these compounds are preferably in the range from 0.1 to 3%.
- the concentration of these compounds and similar components of the mixture are not taken into account when specifying the concentration ranges of the other components of the mixture, unless expressly stated otherwise.
- the media are obtained from the compounds in the usual way.
- the compounds which are used in a smaller amount are expediently dissolved in the compounds used in a larger amount. If the temperature is raised above the clearing point of the predominant component during the mixing process, the completeness of the dissolution can easily be observed.
- the media according to the invention can also be produced in other ways. So through the use of premixes. Among other things, homolog mixtures and / or eutectic mixtures can be used as premixes. However, the premixes can also themselves be usable media. This is the case with so-called two-bottle systems or "multi-bottle systems".
- the specified ranges of values preferably include the limit values.
- the concentrations are given in mass% and relate to the complete mixture. Temperatures are given in degrees Celsius and temperature differences in degrees Celsius. All physical properties were determined as in "Merck Liquid Crystals, Physical Properties of Liquid Crystals", as of Nov. 1997, Merck KGaA, Germany and are given for a temperature of 20 ° C, unless explicitly stated otherwise.
- the optical anisotropy ( ⁇ n) also called birefringence, is determined at a wavelength of 589.3 nm.
- the dielectric properties are determined at a frequency of 1 kHz.
- the properties of the mesogenic control media and in particular that of their achiral components (B) are determined at a temperature of 4 ° below their respective clearing point.
- the cholesteric pitch of cholesteric media or chiral nematic media is determined depending on its size by known methods.
- the material is filled into a thermostatted, wedge-shaped cell with a homogeneous orientation on the substrates.
- the distances between the observed disclination lines are determined and the pitch is calculated using the wedge angle.
- the wedge angle used depends on the pitch to be determined. Cells with a wedge angle of approximately 0.1 ° to 4 °, preferably 0.5 ° to 3 ° and particularly preferably 0.1 ° to 2 ° are typically used.
- the distances between the disclination lines are preferably measured under the microscope. Orientation disorders are taken into account by appropriately averaging the values.
- the mean value of the distances can be determined by diffraction of a laser beam (e.g.
- the diffraction maxima are expediently determined by means of a diode array or a CCD.
- the angle of the wedge cell is preferably determined by multiple reflection of a laser beam. Alternatively, it can be obtained from the geometry of the cell or obtained by a calibration measurement with a material with a known pitch. The measuring accuracy for the pitch is approx. +/- 1% to approx. +/- 3% depending on the measuring method and the current value.
- the lens method is used.
- the material is oriented between a flat plate and a convex lens. Then the distances of the circular disclination lines are measured. This can be done with an image processing system, which simplifies the averaging of the data. From the radius of the lens and the distance of the disclosure line from the contact point, the distance between the lens surface and the flat surface at the location of the disclosure lines is obtained. The measurement accuracy of this method is somewhat less than that of the wedge cells, but a wide range of pitch values can be covered.
- Very small values of the pitch are determined using the selective reflection method.
- the transmission is determined by an oriented sample of the material.
- the pitch is obtained from the wavelength of the maximum of the selective reflection via the refractive index of the material. With this method, the measuring accuracy for the pitch is also approx. +/- 1%.
- the HTP of the chiral materials is determined according to the present application at a temperature of 20 ° C. in the commercial, nematic host mixture MLC-6828 from Merck KGaA, Darmstadt, according to the Grandjean-Cano method.
- the temperature dependence of the HTP is examined in the range from 0 ° C to 50 ° C and is typically given at 20 ° C.
- the HTP is also determined in the commercial, nematic host mixture MLC-6260, also from Merck KGaA.
- the cholesteric pitch of a control medium cannot be determined, it is extrapolated from the HTP of component (A) in component (B). If the value of the HTP of component (A) in component (B) at the corresponding
- Constant that the concentration of the respective material mentioned, ie the component or the compound, in the reference unit, ie the medium or the component, preferably 10% or more, is particularly preferably 20% or more and very particularly preferably 30% or more,
- concentration of the material mentioned in the reference unit is preferably 50% or more, particularly preferably 60% or more and very particularly preferably 70% or more and
- the concentration of the material mentioned in the reference unit is preferably 80% or more, particularly preferably 90% or more and very particularly preferably 95% or more.
- Dielectrically positive connections have a ⁇ > 1.5
- dielectrically neutral connections have a ⁇ in the range -1.5 ⁇ ⁇ 1.5
- dielectrically negative connections have a ⁇ ⁇ -1.5.
- the same definitions also apply to components of mixtures and for mixtures.
- the dielectric properties, electro-optical properties (eg the threshold voltages) and the switching times were determined in test cells manufactured by Merck KGaA, Darmstadt, Germany.
- the test cells for determining ⁇ had a layer thickness of 22 ⁇ m and a circular electrode made of indium tin oxide (ITO) with an area of 1.13 cm 2 and a protective ring.
- ITO indium tin oxide
- lecithin (Merck KGaA) can be used as an orientation aid.
- the cells for the determination of ⁇ ⁇ had orientation layers made of the polyimide AL-1054 from Japan Synthetic Rubber, Japan.
- the capacitances were generally measured using a Solatron 1260 frequency analyzer with a square wave with an effective voltage of 0.3 V rms .
- a lower voltage of 0.1 V rrns is used differently.
- the electro-optical examinations were carried out with white light. The characteristic tensions were determined under vertical observation.
- the dielectric properties of the materials are preferred at a frequency of 1 kHz and, if possible, at 20 ° C. and at
- the dielectric anisotropy ( ⁇ ) of the compounds is determined by extrapolating the values of a 10% solution of the respective compound in a host mixture at 20 ° C. to a proportion of the respective compound of 100%.
- the capacities of the test mixtures are determined both in a cell with a homeotropic and in a cell with a homogeneous edge orientation.
- the layer thickness of both cell types is approx. 20 ⁇ m.
- a square wave with a frequency of 1 kHz and an effective voltage (rms, English: "root mean square") of typically 0.1 V or 0.2 V to 1.0 V is used for the measurement. In any case the voltage used is lower than the capacitive threshold of the mixture under investigation.
- the mixture ZLI-4792 is used for dielectrically positive connections and the mixture ZLI-3086, both from Merck KGaA, Germany, is used as the host mixture for dielectrically neutral and for dielectrically negative connections. These host mixtures are also used for components and media which have no nematic phase even at the temperature in question, or which cannot be supercooled to the temperature in question in the nematic phase. If the solubility of the compounds, components or media in the respective host mixture is less than 10%, the concentration of the investigated substance is exceptionally reduced to 5%.
- solubility of a dielectric positive substance (a compound, a component of a medium or a medium) in the host mixture ZLI-4792 is less than 5%, the nematic mixture MLC-6828, Merck KGaA, Germany used as the host mixture. If necessary, the concentration of the substance to be examined is halved from 10% to 5%. From the change in values compared to that of the host mixture, extrapolation is made to the value of the pure substance.
- the media according to the invention preferably contain 0% to 10% of compounds whose solubility in the corresponding host mixture (ZLI-3086 or MLC-6828) is less than 5%.
- the concentration of these compounds is preferably 8% or less, particularly preferably 5% or less and very particularly preferably 4% or less.
- and ⁇ ⁇ are determined with an absolute accuracy of approximately +/- 0.1 to +/- 0.2, which results in an absolute accuracy of approximately +/- 0.2 to +/- 0.4, typically of +, for the dielectric anisotropy ( ⁇ ) /-0.3 results.
- the accuracy decreases with larger values, so the possible deviations increase.
- the absolute accuracy is approx. +/- 0.5 and with values of more than 40, the absolute accuracy is approx. +/- 1.0.
- the dielectric susceptibility of the media is determined at a temperature of 4 ° above its characteristic temperature. It is called mean dielectric susceptibility ( ⁇ av .) Because it is also, in the first
- the dielectric susceptibility of the media is determined with an absolute accuracy of approx. +/- 0.1 to +/- 0.2. With values of ⁇ av . from 50 or more to 100 the absolute accuracy is approx. +/- 0.5 and for values of more than 100 the absolute accuracy is approx. +/- 2.0.
- the value of the birefringence of components (B) of the media according to the invention is measured here in the nematic phase at 20 ° C. and at a temperature of 4 ° below the clearing point. Is the medium at one of these two temperatures or at these two
- threshold voltage means to the optical threshold and is given for a relative contrast of 10% (V 1 0).
- the mid-gray voltage and the saturation voltage are also determined optically and specified for a relative contrast of 50% and 90%, respectively.
- the voltage (V-io), in exceptional cases also the voltage (V 70 ) is given as the reference variable and characteristic value of the electro-optical characteristic curve of the various media, in which the characteristic curve has a value of 70% for the first time. relative contrast achieved.
- Threshold voltage also called Freedericksz threshold, or the voltage at which 100% relative contrast is reached (V 0 o), this is explicitly stated.
- the media were filled with interdigital electrodes in test cells.
- the layer thickness of the test cells was usually approx. 10 ⁇ m.
- the width of the electrodes was 10 ⁇ m and the distance between the neighboring electrodes was also 10 ⁇ m.
- the electro-optical characteristic was determined at a temperature of 2 degrees above the characteristic temperature of the respective medium.
- the increase in the clearing point was in some cases 0.5 degrees and up to about 0.7 degrees. In a few cases, deviations of up to approx. 2 ° to 4 ° can occur.
- the characteristic temperature (or the clearing point) in the cell is used for characterization.
- 400 nm to 800 nm, preferably 555 nm, are assumed as the wavelength of the light.
- the mesogenic media according to the present application preferably contain
- the media according to the invention according to the present application can contain one or more further compounds in small amounts as stabilizers or for adjusting the specific resistance. They preferably contain one or more stabilizers, preferably selected from the list of the following compounds in Table C. Table C.
- a typical connection that can be used to adjust resistivity has the following formula
- the achiral liquid crystal mixture AM-1 with the following composition was prepared and examined.
- This liquid crystal mixture was filled into a test cell and examined for its electro-optical properties at a temperature of 7.7 ° C. and over a temperature range from 6.2 ° C. to 10.7 ° C. (5 ° above the clearing point).
- the test cell used had interdigital electrodes on only one of the two substrates.
- An electro-optical test cell with a light switching element containing the liquid crystal mixture was produced.
- the Substrates were made of glass.
- Substrates without an orientation layer and without a passivation layer were used.
- the electrode structure consisted of interdigitated comb-shaped electrodes. The distance between the electrodes was 10 ⁇ m and the width of the electrodes was 10 ⁇ m.
- the layer thickness of the electrodes was approximately 100 nm.
- the electrodes were all in a common plane.
- the layer thickness of the control medium was approximately 10 ⁇ m.
- a first polarizer was used in front and a second polarizer behind the cell as the analyzer.
- the absorption axes of the two polarizers formed an angle of 90 ° to one another.
- the angle between the axis of maximum absorption of the polarizers and the component of the electric field in the plane of the display was 45 ° in each case.
- the voltage transmission characteristic was measured with an electro-optical measuring station DMS 703 from Autronic-Melchers,
- a mixture of 97% of the achiral liquid crystal mixture AM-1 of comparative example 1a and 3% of the chiral compound B (OC) 2C * HC-3 is prepared and investigated.
- the chiral compound has c in the form used at 20 ° a HTP of +137 microns "1 (in MLC-6828), and in MLC-6260 of +104 microns.”
- the mixture has a blue phase over a range of approximately 2 degrees with the following phase sequence: N * 11.5 ° C BP 13.5 ° C I.
- Comparative Example 1a As described in Comparative Example 1a, the mixture is filled into a test cell and examined as described. In particular, their electro-optical properties are examined at temperatures up to a few degrees above their characteristic temperature. The results are shown in Table 1 for comparison with those of Comparative Example 1a.
- the characteristic voltage V 7 o of the liquid crystal switching elements of Example 1 at temperatures close to the characteristic temperature is somewhat greater than that of Comparative Example 1a at the corresponding ones Temperatures.
- the characteristic voltage of the liquid crystal switching elements of Example 1 like that of Comparative Example 1a, increases monotonically with increasing temperature.
- the increase in the characteristic voltage in the liquid crystal switching elements of example 1a is initially significantly less than that of comparative example 1, so that the two switching elements already show almost the same voltage V 0 at a temperature of 1.5 ° above their reference temperature.
- the temperature dependency at a temperature of 2 ° above the respective characteristic temperature is reduced in the comparison of the light control elements of comparative example 1a with those of example 1 from over 25% to below 20%.
- the relative temperature dependence of the characteristic voltage is dV * 7 o (/ V 7 o) / dT 9% / D and at a temperature of 2 ° above the characteristic temperature, the relative Temperature dependence of the characteristic voltage dV * 7 o ( ⁇ 7 o) lT 45% / °.
- Example 1 In the mixtures of Example 1 and Comparative Example 1a, cells with an electrode spacing of 15 ⁇ m and an electrode width of 10 ⁇ m were additionally examined. The results are summarized in Table 2.
- BC ⁇ C B (OC) 2C * H-C-3,
- the distance between electrodes of the cells used was, in Table 2, exceptionally 15 ⁇ m.
- the achiral mixture AM-2 of the following composition is prepared and examined.
- the characteristic voltage V 70 of the cell with this doped mixture does not increase with increasing temperature, as in Comparative Example 1a and in Example 1, but rather decreases with increasing temperature then at around -11.6 ° C a minimum and only then rises again with increasing temperature.
- the temperature of -11.6 ° C. is referred to as the characteristic temperature, since the characteristic voltage passes through a minimum.
- the range from a temperature of -19.3 ° C to 13 ° C is specified as the phase range of the blue phase.
- the voltage only reaches 156 V, i.e. less than twice the value of the minimum voltage of 80 V.
- the lower limit of the temperature range is the temperature at which the electro-optical effect can be exploited first. It can be determined from the observed switching time become.
- 164 V is slightly more than twice the value of the minimum voltage.
- the chiral compounds used in the DM-1 dopant mixture all have, with one exception, a high, positive HTP value in the reference mixture with the stated composition.
- V 0 initially decreases with increasing temperature and only then increases again with increasing temperature.
- the minimum of V 7 o is approx. -8.5 ° C.
- the temperature dependence of the characteristic voltage (dV 70 / dT) disappears almost completely (see Table 5 ).
- the liquid crystal mixture AM-2 of Comparative Example 2 was mixed again to 85% as in Example 2b with 15% of that of a dopant mixture.
- the DM-2 dopant mixture with the following composition was used.
- the chiral compounds used in the DM-2 dopant mixture have HTP values in the reference mixture which increase with increasing temperature.
- the resulting mixture has a characteristic temperature.
- the mixture AM-3 was prepared with the following composition.
- Example 3a, 3b and 3c 3%, 5% or 7% of the chiral compound B (OC) 2C * HC-3 used in Example 1 was added to the mixture AM-3 of Comparative Example 3 (Examples 3a, 3b and 3c).
- the resulting mixtures showed a phase transition into the blue phase at approx. 24 ° C, 36 ° C or 46 ° C. 24.3 ° C, 36.3 ° C and 45.9 ° C were assumed as characteristic temperatures.
- Table 7 Characteristic voltages of Examples 3a to 3c
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DE50306222T DE50306222D1 (de) | 2002-11-15 | 2003-11-12 | Elektrooptisches lichtsteuerelement, elektrooptische anzeige und steuermedium |
KR1020057008796A KR101180205B1 (ko) | 2002-11-15 | 2003-11-12 | 전기-광학적 광 변조 소자, 전기-광학적 디스플레이 및 변조 매질 |
DE10393340T DE10393340D2 (de) | 2002-11-15 | 2003-11-12 | Elektooptisches Lichtsteuerelement, elektrooptische Anzeige und Steuermedium |
US10/535,104 US7440160B2 (en) | 2002-11-15 | 2003-11-12 | Electro-optical light modulating element, electro-optical display and modulating medium |
AU2003286165A AU2003286165A1 (en) | 2002-11-15 | 2003-11-12 | Electrooptical light modulating element, electrooptical display and modulating medium |
JP2004570273A JP5841301B2 (ja) | 2002-11-15 | 2003-11-12 | 電気光学的光変調素子、電気光学的ディスプレイおよび変調媒体 |
EP03776899A EP1561150B1 (de) | 2002-11-15 | 2003-11-12 | Elektrooptisches lichtsteuerelement, elektrooptische anzeige und steuermedium |
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DE10313979.6 | 2003-03-27 | ||
DE10313979A DE10313979A1 (de) | 2003-03-27 | 2003-03-27 | Elektrooptisches Lichsteuerelement, elektrooptische Anzeige und Steuermedium |
DE10336783A DE10336783A1 (de) | 2003-08-08 | 2003-08-08 | Elektrooptisches Lichtsteuerelement, elektrooptische Anzeige und Steuermedium |
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Also Published As
Publication number | Publication date |
---|---|
JP2006506515A (ja) | 2006-02-23 |
TW200423709A (en) | 2004-11-01 |
KR101180205B1 (ko) | 2012-09-05 |
KR20050086682A (ko) | 2005-08-30 |
EP1561150B1 (de) | 2007-01-03 |
JP2014225028A (ja) | 2014-12-04 |
DE50306222D1 (de) | 2007-02-15 |
AU2003286165A1 (en) | 2004-06-15 |
JP2012068645A (ja) | 2012-04-05 |
DE10393340D2 (de) | 2005-09-29 |
TWI338499B (en) | 2011-03-01 |
JP6047125B2 (ja) | 2016-12-21 |
WO2004046805A8 (de) | 2005-07-21 |
US20060050354A1 (en) | 2006-03-09 |
US7440160B2 (en) | 2008-10-21 |
JP5841301B2 (ja) | 2016-01-13 |
ATE350684T1 (de) | 2007-01-15 |
EP1561150A1 (de) | 2005-08-10 |
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