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WO1998019207A1 - Corps transparents - Google Patents

Corps transparents Download PDF

Info

Publication number
WO1998019207A1
WO1998019207A1 PCT/EP1997/005749 EP9705749W WO9819207A1 WO 1998019207 A1 WO1998019207 A1 WO 1998019207A1 EP 9705749 W EP9705749 W EP 9705749W WO 9819207 A1 WO9819207 A1 WO 9819207A1
Authority
WO
WIPO (PCT)
Prior art keywords
see
molecules
liquid crystals
orientation
body according
Prior art date
Application number
PCT/EP1997/005749
Other languages
German (de)
English (en)
Inventor
Albert Schmidt
Original Assignee
Carl Zeiss
Carl-Zeiss-Stiftung Handelnd Als Carl Zeiss
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 Carl Zeiss, Carl-Zeiss-Stiftung Handelnd Als Carl Zeiss filed Critical Carl Zeiss
Publication of WO1998019207A1 publication Critical patent/WO1998019207A1/fr

Links

Classifications

    • 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
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
    • G02C7/101—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses having an electro-optical light valve
    • 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 
    • G02F1/0126—Opto-optical modulation, i.e. control of one light beam by another light beam, not otherwise provided for in this subclass

Definitions

  • the invention relates to see-through bodies with two outer transparent end bodies, which enclose a volume arranged between them with liquid crystals and embedded dyes, and in each case an orientation layer made of organic molecules or polymers on the inner surfaces of the end bodies.
  • Transparent bodies with liquid crystals in between are well known and are used in particular in LCD screens.
  • see-through bodies of this type in panes of buildings, cars, trains, aircraft and in sunglasses.
  • the see-through bodies are used in sunglasses to change their transmission in changing light conditions, so that the eye is protected from excessive radiation.
  • Sunglasses which take advantage of the electrochromic effect and require a battery as a voltage source.
  • Sunglasses are also known which take advantage of the electro-optical effect of liquid crystals (LC or FK). Since smaller voltages and powers are sufficient than with the electrochromic effect, the energy supply from one or more photocells is sufficient.
  • LC liquid crystals
  • FK electrochromic effect
  • several dyes have to be embedded in an LC matrix (guest host principle / cell).
  • the application of a voltage leads to a reorientation of the LC molecules from homogeneous planar to homeotropic (or vice versa, depending on the cell type), whereby the spatial position of the dyes is also changed by the interaction with the LC molecules. This changes the absorption of the cell.
  • the orientation layers are either built up from polymers (eg polymide), whereby a preferred direction is generated by brushing, or from organic molecules, which (by themselves) are oriented perpendicularly or with an angle of inclination to the surface.
  • Phototropic glasses do not need any voltage or energy supply. Due to the photochromic effect, the solar radiation causes a photochemical change in the volume of the glasses, which is reflected in the change in absorption.
  • a windshield for a passenger car is known from US Pat. No. 5,298,732, in which an LCD arrangement creates a transmission-reducing area only between the driver and the sun.
  • an additional voltage source is required to change the transmission.
  • liquid crystals in particular natural light or sunlight
  • the invention is essentially based on a combination of guest-host cells with orientation layers that show the command surface effect.
  • the Orientation layer orientation changed. This changes the orientation of the liquid crystals and the dyes. This causes a change in the transmission. This process is reversible.
  • the see-through body according to the invention has two outer transparent shells as the end body, it being possible for the curvature of the shell to produce an optical effect on at least one of the two shells, preferably on the outer side thereof (but not necessarily, see sunglasses).
  • This volume contains liquid crystals and embedded dyes, which are prevented from leaking by the two shells.
  • an orientation layer made of organic molecules or polymers, which is in direct contact with the liquid crystals.
  • the orientation layers are made of photochromic molecules or polymers, which switch the volume of the liquid crystals according to the command surface effect. These are in particular molecules and polymers with cis-trans isomerization. Furthermore, according to the invention, dye molecules are dissolved in the liquid crystals, which are based on the Sunlight spectrum and the visual spectral sensitivity of the human eye or to the spectral sensitivity of a device behind the see-through body are matched.
  • This combination according to the invention makes it possible to create sun-sensitive see-through bodies (sunglasses lenses, panes for various vehicles or buildings, etc.), which are much less expensive than the previously known solutions
  • This insulation layer is advantageously arranged between the transparent conductive electrode and the orientation layer.
  • This insulation layer is preferably made of SiO 2.
  • the orientation layer is preferably made up of azobenzenes or molecules (or polymers) containing stilbene.
  • the liquid crystals are preferably nematic liquid crystals.
  • the end bodies are preferably made of plastic or glass.
  • the preferred area of use of the see-through body is its use as a lens for sunglasses.
  • Figure 1 shows a first see-through body according to the invention
  • Figure 2 shows another variant of a see-through body according to the invention.
  • the see-through bodies shown in FIGS. 1 and 2 are drawn purely theoretically, so that the size relationships shown are unrelated to the real size relationships.
  • the see-through bodies can in particular be lenses for sunglasses, windows for buildings, cars, trains, planes, etc., the lenses being able to have, in particular, one or no dioptric effect.
  • the structure of the see-through body is quickly explained.
  • the first see-through body (1) according to the invention shown in FIG. 1 shows a feasible minimal solution. It has two cover layer bodies (la, lb) which create a cavity and which consist of a transparent hard or soft material.
  • This material can e.g. Be glass on which the command surface layers can be applied using chemisorption or the Langmuir-Blodgett technique. It can also be applied to plastic using the Langmuir-Blodgett technique. However, one can also first apply a thin SiO 2 layer to plastics, on which the command surface layers can be applied.
  • An orientation layer (2a, 2b) is in each case applied to the inner surface of these cover layer bodies (la, lb).
  • the cavity between the two cover layer bodies (la, lb) with the orientation layer (2a, 2b) on its inner surface is filled with rod-shaped liquid crystals (3) which have a dye admixture according to the prior art, so that the guest host Principle is used.
  • the orientation layer (2a, 2b) is the essential part of the invention. It consists of molecules, which undergo a cis-trans isomerization under the influence of UV radiation and thus change geometrically. The geometric change leads to a change in the position of the liquid crystals (3) lying on the orientation layer (2a, 2b), which ultimately leads to a positional adjustment of all liquid crystals (3) between the two orientation layers (2a, 2b).
  • Switching speed of such an orientation layer (2a, 2b) is currently in the seconds / minutes range with the previously known molecules and depends on the length of the molecules (the longer the molecules are, the faster they change from one state to the other state ).
  • Molecules for the orientation layer (2a, 2b) are photochromic molecules with the isomerization described above. Examples include azobenzenes and stilbenes.
  • one layer of a molecule or polymer e.g. azobenzene
  • the orientation layer (2a, 2b) and with it the liquid crystal (3) changes its orientation from the homeotropic phase in the trans state to the homogeneous planar phase in the cis state, which is oriented along the direction of transmission, when using azobenzene molecules in the orientation layer (2a, 2b) when irradiated with a wavelength of approximately 360nm.
  • the opposite change in orientation occurs when irradiated with a wavelength of approximately 440 nm.
  • FIG. 2 A further variant of the see-through body (1 ') according to the invention is shown in FIG. 2, but which has a much more complicated layer structure between the two cover layer bodies (la 1 , lb').
  • a transparent electrode (5a, 5b) for example an indium tin oxide, also called ITO
  • ITO indium tin oxide
  • An insulating layer (4a, 4b) for example made of SiO 2 is deposited thereon, but this is not mandatory.
  • the orientation layer follows
  • a coupling layer (not shown in the figure) can also be applied between the orientation layer (2a ', 2b') and the insulating layer (4a, 4b) or electrode (5a, 5b). Between the two orientation layers
  • (2a 1 , 2b ') are the liquid crystals (3') with the dye admixture (guest-host principle).
  • the see-through bodies can then also be used as sunglasses lenses behind windows (e.g. in a building or in a car).
  • the invention is characterized by a combination of the guest-host principle with the command surface effect.
  • the volume of the liquid crystal cell is not changed photochemically, as is the case with phototropic glasses, but only the orientation layer between the cover layer bodies and the liquid crystals, it being possible for an electrode to be attached between the orientation layer and the cover layer bodies.
  • the orientation layer gives the liquid crystals a uniform orientation. It is known from some special orientation layers described above that they change their chemical and physical structure by exposure to UV and can switch a liquid crystal cell from homeotropic to homogeneous planar and thus can trigger a command surface effect.
  • the advantage of the inventive solution, especially for sunglasses is the absence or not necessarily the presence of any power supply and electronics.
  • only an extremely thin layer is changed photochemically, while the volume of the liquid crystal cell is not photochemically loaded.
  • the change in transmission in the see-through bodies according to the invention is less than 40% (but 25-30% are certain) with a maximum transmission of approximately 75% and less.
  • Suitable photochromic molecules for use as a "command surface layer” are molecules which show a cis-trans photoisomerization when irradiated, which is associated with a change in the geometry of the molecule.
  • the best known examples are the stilbene derivatives and the azobenzene derivatives.
  • the coupling layer between the surface and the photochromic function is typically integrated into the whole molecule (the R ] _ in the above nomenclature).
  • the R ] _ in the above nomenclature.
  • the molecules in the in general, have the following schematic structure:
  • Head group photochromic group, spacer, anchor group.
  • the anchor group connects the molecule to the substrate surface.
  • the spacer separates the photochromic group from the surface (since this group needs space to carry out the isomerization).
  • the head group is the free end of the molecule. This serves to create space for the photochromic groups and the connection. to ensure the liquid crystals in the cell.
  • the simplest type of head group are alkyl chains of different lengths, n.
  • the spacer is also an alkyl chain of length m.
  • the chemistry of the system often requires an alkoxy group as the head group.
  • the anchor group can be chemically bound to the surface (typically glass, quartz, silica). This happens, for example, through silane compounds:
  • the substrate must be pretreated with an appropriate reagent (e.g. glass / quartz surface):
  • an appropriate reagent e.g. glass / quartz surface
  • Physical interactions can also occur that bind the molecule to the surface (physisorption). Examples of these are molecules that can be applied to surfaces as monomolecular films using the Langmuir-Blodgett method. Another option is to use the anchor group as a Train polymer. Then several (spacer photochromic head group) systems are bound to a main polymer chain. This main chain then acts as an anchor group. The connection to the surface takes place via physical effects (example: ionic / electrostatic or Van der Waals interaction). Some representatives of such polymers can also be applied using the Langmuir-Blodgett method. Examples include:
  • the above azobenzene functionalized polyglutamates a) poly (5- (x- (4- (4-hexylphenylazo) phenoxy) ethyl) -L-glutamate, and b) poly (5- (2- (4- (4-decyloxyphenylazo ) phenoxy) ethyl) -L-glutamate.
  • the well-known azobenzene derivatives are based on a unidirectional, homeotropic starting orientation of the orientation layer of the LC cell.
  • LC mixtures with (positive) dielectric anisotropy and pleochroic dyes or dye mixtures which are used in the LC mixture are soluble.
  • Examples of the LC mixture are ZLI1840 from Merck and the dye G313 (2.5%) (manufacturer is, for example, Merck), with maximum absorption at 666 nm. This cell appears bright in the off state (without exposure) On state (with exposure) the cell appears green.
  • a polarizer For the highest possible contrast, a polarizer should be used, the orientation of which is adapted to the unidirectional orientation of the orientation layer.
  • the switching times of the effect are in the minute range.
  • the switching time can be shortened by changing the molecular parameters, such as lengthening the spacer or increasing the interaction between liquid crystal and the photochromic unit (polar group in the center of the liquid crystal molecule).

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  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Liquid Crystal (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Mathematical Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Health & Medical Sciences (AREA)

Abstract

L'invention concerne des corps transparents présentant deux corps d'extrémité extérieurs transparents entourant un volume disposé entre eux, formé de cristaux liquides et de colorants intercalés (cellules à cristaux liquides dichroïques), une couche d'orientation formée de molécules ou de polymères organiques étant appliquée sur la surface interne de chacun desdits corps d'extrémité. L'invention est caractérisée en ce que les couches d'orientation sont constituées de molécules ou de polymères photochromes qui, suivant l'effet de surface contrôlé (en particulier avec isomérisation cis-trans), régulent le volume des cristaux liquides et en ce que des molécules de colorant sont dissoutes dans les cristaux liquides, molécules qui sont adaptées au spectre de la lumière solaire et à la sensibilité spectrale visuelle de l'oeil humain ou à la sensibilité spectrale d'un appareil placé à l'arrière des corps transparents.
PCT/EP1997/005749 1996-10-28 1997-10-17 Corps transparents WO1998019207A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19644726.7 1996-10-28
DE1996144726 DE19644726A1 (de) 1996-10-28 1996-10-28 Durchsichtkörper

Publications (1)

Publication Number Publication Date
WO1998019207A1 true WO1998019207A1 (fr) 1998-05-07

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ID=7810193

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1997/005749 WO1998019207A1 (fr) 1996-10-28 1997-10-17 Corps transparents

Country Status (2)

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DE (1) DE19644726A1 (fr)
WO (1) WO1998019207A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6690495B1 (en) 2000-10-03 2004-02-10 Alphamicron, Inc. Device exhibiting photo-induced dichroism for adaptive anti-glare vision protection
US7044600B2 (en) 2004-01-14 2006-05-16 Ppg Industries Ohio, Inc. Polarizing devices and methods of making the same
US7256921B2 (en) 2003-07-01 2007-08-14 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
US7342112B2 (en) 2003-07-01 2008-03-11 Ppg Industries Ohio, Inc. Photochromic compounds
US7632540B2 (en) 2003-07-01 2009-12-15 Transitions Optical, Inc. Alignment facilities for optical dyes
US8518546B2 (en) 2003-07-01 2013-08-27 Transitions Optical, Inc. Photochromic compounds and compositions
US8545984B2 (en) 2003-07-01 2013-10-01 Transitions Optical, Inc. Photochromic compounds and compositions
US8582192B2 (en) 2003-07-01 2013-11-12 Transitions Optical, Inc. Polarizing photochromic articles
US8698117B2 (en) 2003-07-01 2014-04-15 Transitions Optical, Inc. Indeno-fused ring compounds
US9096014B2 (en) 2003-07-01 2015-08-04 Transitions Optical, Inc. Oriented polymeric sheets exhibiting dichroism and articles containing the same
US10000472B2 (en) 2003-07-01 2018-06-19 Transitions Optical, Inc. Photochromic compounds
US10866455B2 (en) 2017-10-19 2020-12-15 Ppg Industries Ohio, Inc. Display devices including photochromic-dichroic compounds and dichroic compounds
CN114911099A (zh) * 2021-02-08 2022-08-16 曹汉伟 偏光变色膜片、镜片及眼镜

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
JP2003502693A (ja) * 1999-06-11 2003-01-21 ピーピージー・インダストリーズ・オハイオ・インコーポレイテッド 電気光学デバイスとそれを用いた可変透明物品
DE10033535A1 (de) * 2000-07-11 2002-01-31 Ingbuero Dr Ing Harald Schulz Doppelfassade
DE102013101530A1 (de) 2013-02-15 2014-08-21 Osram Opto Semiconductors Gmbh Optoelektronisches Halbleiterbauteil
US9159890B2 (en) 2013-02-15 2015-10-13 Osram Opto Semiconductors Gmbh Optoelectronic semiconductor component

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Patent Citations (2)

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US5296321A (en) * 1989-07-03 1994-03-22 Agency Of Industrial Science & Technology Photorecording element, method for production thereof, and the liquid crystal cell comprising the same
JPH0519260A (ja) * 1991-07-09 1993-01-29 Victor Co Of Japan Ltd 液晶ライトバルブ

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Title
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Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6690495B1 (en) 2000-10-03 2004-02-10 Alphamicron, Inc. Device exhibiting photo-induced dichroism for adaptive anti-glare vision protection
US6999220B2 (en) 2000-10-03 2006-02-14 Alphamicron, Inc. Device exhibiting photo-induced dichroism for adaptive anti-glare vision protection
US7505189B2 (en) 2003-07-01 2009-03-17 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
US8545984B2 (en) 2003-07-01 2013-10-01 Transitions Optical, Inc. Photochromic compounds and compositions
US10619018B2 (en) 2003-07-01 2020-04-14 Transitions Optical, Inc. Oriented polymeric sheets exhibiting dichroism and articles containing the same
US7256921B2 (en) 2003-07-01 2007-08-14 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
US7286275B2 (en) 2003-07-01 2007-10-23 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
US7342112B2 (en) 2003-07-01 2008-03-11 Ppg Industries Ohio, Inc. Photochromic compounds
US7349138B2 (en) 2003-07-01 2008-03-25 Ppg Industries Ohio, Inc. Polarizing, photochromic devices and methods of making the same
US7349137B2 (en) 2003-07-01 2008-03-25 Ppg Industries Ohio, Inc. Polarizing, photochromic devices and methods of making the same
US7359104B2 (en) 2003-07-01 2008-04-15 Ppg Industries Ohio, Inc. Polarizing, photochromic devices and methods of making the same
US7394585B2 (en) 2003-07-01 2008-07-01 Ppg Industries Ohio, Inc. Polarizing, photochromic devices and methods of making the same
US7429105B2 (en) 2003-07-01 2008-09-30 Ppg Industries Ohio, Inc. Polarizing, photochromic devices and methods of making the same
US7457025B2 (en) 2003-07-01 2008-11-25 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
US7466469B2 (en) 2003-07-01 2008-12-16 Ppg Industries Ohio, Inc. Polarizing, photochromic devices and methods of making the same
US7471436B2 (en) 2003-07-01 2008-12-30 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
US10532997B2 (en) 2003-07-01 2020-01-14 Transitions Optical, Inc. Photochromic compounds
US7632540B2 (en) 2003-07-01 2009-12-15 Transitions Optical, Inc. Alignment facilities for optical dyes
US10532998B2 (en) 2003-07-01 2020-01-14 Transitions Optical, Inc. Photochromic compounds
US8582192B2 (en) 2003-07-01 2013-11-12 Transitions Optical, Inc. Polarizing photochromic articles
US8518546B2 (en) 2003-07-01 2013-08-27 Transitions Optical, Inc. Photochromic compounds and compositions
US8698117B2 (en) 2003-07-01 2014-04-15 Transitions Optical, Inc. Indeno-fused ring compounds
US8926091B2 (en) 2003-07-01 2015-01-06 Transitions Optical, Inc. Optical elements with alignment facilities for optical dyes
US9096014B2 (en) 2003-07-01 2015-08-04 Transitions Optical, Inc. Oriented polymeric sheets exhibiting dichroism and articles containing the same
US9309455B2 (en) 2003-07-01 2016-04-12 Transitions Optical, Inc. Indeno-fused ring compounds
US10000472B2 (en) 2003-07-01 2018-06-19 Transitions Optical, Inc. Photochromic compounds
US10007038B2 (en) 2003-07-01 2018-06-26 Transitions Optical, Inc. Optical elements with alignment facilities for optical dyes
US10005763B2 (en) 2003-07-01 2018-06-26 Transitions Optical, Inc. Photochromic compounds
US10501446B2 (en) 2003-07-01 2019-12-10 Transitions Optical, Inc. Photochromic compounds
US7097304B2 (en) 2004-01-14 2006-08-29 Transitions Optical Inc. Polarizing devices and methods of making the same
US7044600B2 (en) 2004-01-14 2006-05-16 Ppg Industries Ohio, Inc. Polarizing devices and methods of making the same
US7097303B2 (en) 2004-01-14 2006-08-29 Ppg Industries Ohio, Inc. Polarizing devices and methods of making the same
US10866455B2 (en) 2017-10-19 2020-12-15 Ppg Industries Ohio, Inc. Display devices including photochromic-dichroic compounds and dichroic compounds
CN114911099A (zh) * 2021-02-08 2022-08-16 曹汉伟 偏光变色膜片、镜片及眼镜
CN114911099B (zh) * 2021-02-08 2024-03-26 曹汉伟 偏光变色膜片、镜片及眼镜

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Publication number Publication date
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