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WO1999067682A1 - Dispositifs electro-optiques contenant des electrolytes reagissant a la lumiere visible - Google Patents

Dispositifs electro-optiques contenant des electrolytes reagissant a la lumiere visible Download PDF

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Publication number
WO1999067682A1
WO1999067682A1 PCT/US1999/014067 US9914067W WO9967682A1 WO 1999067682 A1 WO1999067682 A1 WO 1999067682A1 US 9914067 W US9914067 W US 9914067W WO 9967682 A1 WO9967682 A1 WO 9967682A1
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WIPO (PCT)
Prior art keywords
ion
electrochromic
electroconductive
conducting polymer
tpo
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PCT/US1999/014067
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English (en)
Inventor
Carol L. Knox
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PPG Industries Ohio Inc
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PPG Industries Ohio Inc
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Application filed by PPG Industries Ohio Inc filed Critical PPG Industries Ohio Inc
Priority to AU45823/99A priority Critical patent/AU4582399A/en
Publication of WO1999067682A1 publication Critical patent/WO1999067682A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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 
    • G02F1/15—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 an electrochromic effect
    • G02F1/1514—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 an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material
    • G02F1/1523—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 an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material comprising inorganic material
    • G02F1/1525—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 an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material comprising inorganic material characterised by a particular ion transporting layer, e.g. electrolyte

Definitions

  • the instant invention is directed to an electrooptic device which contains an improved ion-conducting polymer interlayer.
  • This improved electrolyte is polymerized using a trimethylbenzoyldiphenyl phosphine oxide-based initiation system.
  • the transmittance properties of electrochromic materials change in response to electrically driven changes in oxidation state.
  • an applied voltage from an external power supply causes electrons to flow to (reduction) or from (oxidation) an electrochromic material
  • its transmittance properties change.
  • a charge balancing flow of ions in the electrochromic device is needed.
  • electrochromic devices comprise at least one thin film of a persistent electrochromic material, i.e. a material responsive to the application of an electric field to change from a high-transmittance, non-absorbing state to a low-transmittance, absorbing or reflecting state. Since the degree of optical modulation is directly proportional to the current flow induced by an applied voltage, electrochromic devices demonstrate light transmission tunability between high- ransmittance and low-transmittance states. In addition, these devices exhibit long-term retention of a chosen optical state, requiring no power consumption to maintain that optical state. Optical switching occurs when an electric field of reversed polarity is applied.
  • an electrochromic film which is both an ionic and electronic conductor is in ion-conductive contact, preferably direct physical contact, with an ion-conducting material layer.
  • the ion-conducting material may be inorganic or organic, solid, liquid or gel, and is preferably an organic polymer.
  • the electrochromic film(s) and ion-conducting material are disposed between two electrodes, forming a laminated cell. As voltage is applied across the electrodes, ions are conducted through the ion-conducting material.
  • an electrochromic film such as tungsten oxide is deposited on a substrate coated with an electroconductive film such as tin oxide or indium tin oxide to form one electrode.
  • the counter electrode is typically a similar tin oxide or indium tin oxide coated substrate.
  • a complimentary electrochromic film for example an iridium oxide film, can also be used.
  • the polymeric electrolyte material is a hydrophilic copolymer of a selected acrylate or methacrylate monomer and a selected acid group containing a monomer, such as 2-acrylamido-2-methylpropanesulfonic acid (A PSA) .
  • a PSA 2-acrylamido-2-methylpropanesulfonic acid
  • U.S. Pat. No. 4,335,938 to Giglia discloses electrochromic devices having a layer of tungsten oxide in contact with a layer of organic electrolyte resin comprising a hydrophilic layer of 2-acrylamido-2-methylpropanesulfonic acid homopolymer and an electrode means for changing electrochromic properties of the device.
  • electrochromic devices having a layer of electrochromic tungsten oxide in contact with a polymeric electrolyte wherein the stability and speed of the device are improved by using a copolymer of 2-acrylamido-2- methylpropanesulfonic acid and vinyl sulfonic acid as the polymer electrolyte.
  • U.S. Pat. No. 5,471,338 to Yu, et al . , and U.S. Pat. No. 5,471,554 to Rukavina, et al . disclose lamination of two coated plastic substrates using an ion-conducting polymer interlayer which bonds the coated surfaces to form a composite.
  • Homo and copolymers of 2 -acrylamido-2 -methyl propyl sulfonic acid (AMPSA) form the ion-conducting polymer layer and are cured using actinic radiation, preferably (UV) light.
  • actinic radiation preferably (UV) light.
  • AMPSA/N,N-dimethylacrylamide (DMA) polymers are preferred, and benzoin methyl ether and diethoxyacetophenone are disclosed as UV initiators.
  • PCT WO 93/04096 discloses a method for preparing homo and copolymers of AMPSA, including AMPSA/DMA copolymers, using a photosensitizer and light to initiate polymerization.
  • U.S. Pat. No. 5,327,281 to Cogan discloses the use of ionomers such as AMPSA/DMA polymers as polymer electrolytes in electrochromic devices.
  • EPO 795 765 A2 discloses the use of 2,4,6- trimethylbenzoyldiphenyl phosphine oxide as an initiator for photopolymerizable oligomers used to form highly refractive plastic lenses.
  • Figure 1 is a vertical cross-sectional view of one embodiment of the electrooptic device of the present invention. Cross-hatching is used to differentiate various laminate layers, and does not represent any material of construction. Figure 1 is not drawn to scale.
  • Electrooptic device 1 comprises first electrochromic layer 2 and second electrochromic layer 4, both of which are in ion-conductive contact with improved ion- conducting polymer layer 3.
  • Layers 2, 3 and 4 are situated between first and second electroconductive layers 5 and 6, which are disposed on first and second substrates 7 and 8, respectively.
  • Improved ion-conducting polymer layer 3 is prepared using a 2 , 4 , 6-trimethylbenzoyldiphenyl phosphine oxide (TPO) - based initiation system. More particularly, a monomer solution comprising one or more monomers useful in preparing an ion-conducting polymer suitable for use in an electrooptic device and an effective amount of TPO is cast between first and second coated substrates used to prepare laminated electrooptic device 1. Polymerization, which occurs in situ, is initiated by exposing the monomer solution to free radical- generating electromagnetic energy, preferably visible light. In a preferred embodiment, initiating energy passes through at least one of the coated substrates en route to the monomer solution.
  • TPO 6-trimethylbenzoyldiphenyl phosphine oxide
  • Coated substrates used to prepare electrochromic devices generally have poor transmittance characteristics in the UV region. This characteristic usually makes the use of UV initiators, such as diethoxyacetophenone (DEOAP) inefficient relative to curing monomer solutions situated between such substrates.
  • UV initiators such as diethoxyacetophenone (DEOAP)
  • TPO diethoxyacetophenone
  • the instant invention provides improved cure rates through coated electrochromic substrates while improving process safety by eliminating the need to handle UV light. Further, TPO generally does not cause substantial polymer yellowing, which is a problem typical of visible light initiators.
  • the instant invention is directed to an electrooptic device containing an ion- conducting polymer layer prepared using a 2,4,6- trimethylbenzoyldiphenyl phosphine oxide-based initiator system.
  • Preferred electrooptic devices are electrochromic devices, such as electrochromic lenses, prepared using a TPO/visible light initiation system.
  • this invention is directed to an electrooptic device comprising: a) a first electroconductive layer; b) an electrochromic layer disposed on said first electroconductive layer, these two elements constituting together a first electrode; c) a counter-electrode comprising a second electroconductive layer and, optionally, a second electrochromic layer disposed on said second electroconductive layer; and d) an ion-conducting polymer layer which is disposed between the first electrode and the counter- electrode, wherein said ion-conducting polymer layer is formed using a TPO-based initiation system.
  • the ion- conducting polymer layer is formed in situ between the electrodes by casting or placing a TPO containing monomer solution between the electrodes and passing visible light through at least one of the electrodes, thereby initiating TPO-based free radical polymerization of the monomer solution.
  • the electrode and counter-electrode layers can be deposited on any suitable substrate.
  • the first and second substrates which can be the same or different, are light transmitting materials, preferably transparent materials such as glass or plastic which are suitable for producing lenses used in eyewear.
  • Plastic eyewear substrates preferably contain one or more conventional UV absorbers to protect them from degradation and/or yellowing and to protect the user's eyes from UV light.
  • a preferred embodiment of the instant invention is directed to an electrochromic device comprising: a. a first substrate, preferably a transparent polymeric substrate, said substrate optionally containing a primer which improves the adherence of a metal oxide film; b. a first electroconductive metal oxide film deposited on said first substrate or on a primer deposited thereon; c. a first electrochromic film deposited on said first electroconductive metal oxide film; d. a second substrate, preferably a transparent polymeric substrate, said substrate optionally containing a primer which improves the adherence of a metal oxide film; e. a second electroconductive film deposited on said second substrate or on a primer deposited thereon; f.
  • a second complementary electrochromic film deposited on said second electroconductive film; and g. an ion-conducting polymer layer disposed between the coated first and second substrates described above, wherein said ion-conducting polymer layer is formed using a TPO-based initiation system.
  • the present invention is also directed to a method for preparing a laminated electrochromic device, said device comprising first and second coated substrates having electroconductive films and at least one electrochromic film thereon, which method comprises: a) placing an effective amount of a polymerizable monomer solution comprising one or more monomers suitable for forming, upon polymerization, an ion-conducting polymer and an effective amount of TPO, between said first and second coated substrates; b) bringing said coated substrates together so that their mating surfaces contact said monomer solution; and c) exposing said monomer solution to electromagnetic energy suitable for generating TPO-based free radicals, preferably by passing said energy through at least one of said coated substrates, thereby initiating polymerization of said monomer solution and laminating said coated substrates.
  • the preferred electromagnetic energy is visible light.
  • the instant invention is also directed to an improved method for laminating an electrochromic device comprising first and second coated substrates bonded by an ion-conducting polymer, wherein the improvement comprises forming the ion- conducting polymer in situ between said coated substrates via use of a TPO-based, preferably a TPO/visible light, initiation system.
  • a TPO-based, preferably a TPO/visible light, initiation system preferably a TPO/visible light, initiation system.
  • a TPO-initiated ion-conducting polymer layer is disposed between and bonds the mating surfaces of the device substrates .
  • a key step in a typical photoinitated polymerization process involves free radical generation due to absorption of electromagnetic radiation by a polymerization initiator present in the monomer solution to be polymerized. This requires that the absorption band of the initiator overlap the emission band of the energy source that it is exposed to.
  • TPO which is characterized by a peak absorbance at 385 nm
  • UV-absorbing initiators e.g., tin-doped indium oxide
  • electrochromic films do not effectively transmit UV light below about 350 nm. This limits the use of UV-absorbing initiators, since the small amount of UV energy which passes through such substrates may not be sufficient to efficiently cure a monomer solution in cases where curing is effectuated by passing UV energy through a coated substrate. This problem is further compounded if the substrate contains a UV absorber.
  • a TPO- based initiation system remedies this problem by allowing the use of visible light, which is transmitted through substrates containing conventional electrochromic coatings and, optionally, UV absorbers, to cure monomer systems cast between the coated substrates of electrochromic devices.
  • the term 'TPO-based initiation system' refers to the application of sufficient electromagnetic radiation of appropriate wavelength to a TPO- containing monomer solution to generate TPO-based free radicals, thereby initiating polymerization.
  • An effective amount of TPO and energy is used, that being an amount of each necessary to initiate polymerization for a given monomer system. Determination of effective TPO and energy levels for a given system is well within the purview of skilled practitioners .
  • UV light can be used in conjunction with TPO, visible light is preferred.
  • any visible light source having an emission band which overlaps the TPO absorption band can be used.
  • fluorescent or incandescent lamps can be used, with fluorescent lamps being preferred. These lights generally produce about 50 to about 80 lumens per watt, whereas incandescent lights generally produce about 17 to about 23 lumens per watt.
  • particular fluorescent lights generate narrow wavelength bands which are more specific than the scattered wavelengths of incandescent light.
  • fluorescent lights unlike incandescent lights, fluorescent lights generally do not generate ultraviolet or infrared light.
  • Mercury arc lamps are also suitable visible light sources.
  • the laminated electrochromic devices of this invention contain an ion-conducting polymer layer disposed between the mating surfaces of first and second coated substrates.
  • Various ion-conducting polymers can be used.
  • Preferred ion-conducting polymers serve the dual functions of being ion-conducting electrolytes and mechanical adhesives.
  • Suitable ion-conducting polymers include the polymers known as ionomers described in U.S. Patent No. 5,327,281 to Cogan and Rauh, which is incorporated herein by reference in its entirety. These polymers are generally formed by casting and polymerizing solutions containing monomers bearing both an ionizable group and an ethylenic, e.g.
  • the ion-conducting polymer is a proton- conducting polymer selected from the group consisting of homopolymers of 2-acrylamido-2-methylpropanesulfonic acid (AMPSA) and copolymers of AMPSA with various monomers, for example N,N-dialkyl (meth) acrylamides .
  • AMPSA 2-acrylamido-2-methylpropanesulfonic acid
  • meth N,N-dialkyl
  • Such polymers are formed using TPO-containing reaction mixtures of monomers which are cast and cured in place between the coated substrates of an electrochromic device.
  • a more preferred proton-conducting polymer electrolyte in accordance with the present invention is a copolymer of AMPSA and N,N- dimethylacrylamide (DMA) .
  • the thickness of the ion- conducting polymer layer is not believed to be critical but in general is in the range of 0.001 to 0.025 inch (0.0254 to 0.625 millimeter) .
  • Cast-in-place methods of lamination are known in the art .
  • a preferred method for laminating electrochromic devices is the suspension lamination technique disclosed in copending U.S. patent application Serial No.
  • ion-conducting polymers are formed in situ between the electrodes of electrochromic devices by depositing a polymerizable monomer solution comprising one or more monomers and an initiator onto one of the electrodes, distributing the monomer solution between the electrodes by bringing them together, and exposing the initiator in the monomer solution to an energy source during suspension, thereby initiating suspension polymerization of the monomer solution.
  • the first and second substrates of the instant laminated electrochromic devices can be of any suitable material.
  • Preferred substrates are light transmitting materials such as glass or plastic. More preferably, transparent lenses are used.
  • Suitable transparent lenses may have a conventional refractive index (1.48-1.5), a relatively high refractive index (1.60-1.75), or a mid-range refractive index (1.51-1.59), depending on the end use.
  • a transparent lens may have a refractive index within the range of between 1.48 and 1.75, e.g., from about 1.50 to about 1.8.
  • Synthetic polymer substrates that may be used as a lens material include, but are not limited to: thermoplastic polycarbonates, such as the carbonate-linked resin derived from bisphenol A and phosgene, which is sold under the trademark LEXAN; polyesters, such as the material sold under the trademark, MYLAR; poly (methylmethacrylates) , such as the material sold under the trademark, PLEXIGLAS; and polymerizates of a polyol (allyl carbonate) monomer, especially diethylene glycol bis (allyl carbonate) , which is sold under- the trademark CR-39®. Copolymers of the aforedescribed monomers/resins may also be used as a lens material. These and other transparent and non-transparent polymeric substrates known in the art for use for various optical and non-optical applications may be used.
  • the electrochromic substrates of this invention generally contain electroconductive films and at least one electrochromic film, i.e. a film of a persistent electrochromic material which in response to the application of an electric field of a given polarity and sufficient voltage changes from a high-transmittance, non-absorbing state to a lower-transmittance, absorbing or reflecting state. When an electric field of opposite polarity is applied to the electrochromic material, it switches back to a high- transmittance state.
  • the electrochromic film which is both an ionic and electronic conductor, is in ion-conductive contact, preferably direct physical contact, with an ion- conducting polymer.
  • the electrochromic film and ion-conducting polymer are disposed between two electrodes (i.e., electroconductive films) to form an electrochromic cell.
  • a complementary electrochromic film is also present in the cell, while in other applications an optically passive film or metal is used in place of the complementary electrochromic film to form the cell.
  • a cathodically coloring electrochromic material for example tungsten oxide or compounds thereof, is deposited at a thickness of about 1,000 to 6,000 Angstroms on a transparent substrate that has been previously coated with a transparent electroconductive metal oxide film, such as tin oxide or indium tin oxide (ITO) .
  • a transparent electroconductive metal oxide film such as tin oxide or indium tin oxide (ITO) .
  • ITO indium tin oxide
  • the electrocor.ductive film comprises indium and tin at a weight ratio of about 90:10.
  • the film thickness is preferably in the range of about 800-4,000
  • electroconductive and electrochromic films may be deposited by a variety of methods so long as the substrate is not deleteriously affected.
  • the adhesion of an electroconductive metal oxide film directly to a plastic substrate may be improved by application of a primer, such as an organo silane hardcoat, to said substrate prior to coating.
  • a primer such as an organo silane hardcoat
  • the counter electrode is prepared by depositing a similar metal oxide (e.g., indium tin oxide) coating on a second transparent substrate, with or without a complimentary electrochromic film.
  • a suitable complimentary electrochromic film is a nitrogen-containing iridium oxide film as disclosed in U.S. Patent No. 5,618,390 to Yu, Backfisch, et al .
  • the ion conducting polymer is then disposed between substrates so coated as previously described.
  • Composite electrochromic eyeglass lenses can be prepared in accordance with the instant invention by bonding first and second coated lenses together. Bonding is preferably accomplished by placing an effective amount of a curable ion-conducting polymer composition, i.e. a monomer solution comprising one or more monomers, an effective amount of 2 , 4 , 6-trimethylbenzoyldiphenyl phosphine oxide and optionally up to one or more non-reactive diluents and/or additives, on the concave mating surface of a matched lens pair and moving this concave surface ar.d the convex surface of the corresponding lens toward each other, thereby spreading the curable adhesive composition between the lenses.
  • a curable ion-conducting polymer composition i.e. a monomer solution comprising one or more monomers, an effective amount of 2 , 4 , 6-trimethylbenzoyldiphenyl phosphine oxide and optionally up to one or more non-reactive diluents and
  • the curable ICP composition is then cured in situ by visible light which preferably passes through at least one of the coated lenses. Curing of the polymer forms ar. ion-conducting polymer layer between the lenses while bonding the lenses into a laminate, thereby facilitating necessary ion flow. If organic substrates are used, the instant invention permits the addition of an effective amount of an ultraviolet light stabilizer to the substrates. Such UV absorbers typically absorb wavelengths up to the 350-380 nm range.
  • the TPO-containing monomer solutions of this_ invention are generally poured, cast or otherwise placed between two coated substrates prior to initiation. It may be desirable to place a 0.0015 to 0.020 inch (0.127 to 0.508 millimeter) Teflon® spacer between the substrates, said spacer being held in place with a commercially available sealant such as Torr Seal® from Varian Vacuum Products.
  • the monomer solution is preferably poured onto the concave surface of one lens and the convex surface of the other lens may be placed over the monomer solution, thus forming the solution into a thin film. Exposure to visible light, preferably fluorescent light, sufficient to initiate and cure the polymer electrolyte, essentially completes the lamination process.
  • the present invention is also directed to laminated electrochromic devices prepared by the improved method described above.
  • Example 1 Preparation of TPO-Initiated and DEOAP-Initiated AMPSA/DMA Ion-Conducting Polymers; Comparative Cure Times The following raw materials were used:
  • AMPSA 2-acrylamido-2-methyl-l-propanesulfonic acid
  • DMA N,N-dimethylacrylamide
  • AMPSA/DMA monomer solutions were polymerized using DEOAP and TPO photo-initiators.
  • the monomer solutions contained: 46.5 percent DMA, 27.5 percent AMPSA, 19.3 percent distilled water, 6.1 percent NMP and 0.6 percent DEOAP or TPO, based on weight. These components were weighed into a beaker and stirred with a magnetic stirrer at ambient temperature until the AMPSA was completely dissolved.
  • Table 1 shows that TPO reduces AMPSA/DMA cure times substantially. Also, DEOAP, a conventional UV initiator, was ineffective when curing energy passed through a UV coated lens .
  • a laminated electrochromic lens was prepared using a TPO-initiated ion-conducting polymer by a cast-in-place technique as described below.
  • the edging, priming, cleaning, coating, charging and laminating aspects of this example are not part of the instant invention.
  • the edged lenses were cleaned and dried using an ultrasonic cleaning system.
  • the parts had been previously primed with an organosilane hard coat.
  • Thin films of In 2 0 3 :Sn0 2 (ITO) were then deposited onto the mating surfaces of the primed plastic substrates using direct current (dc) magnetron sputtering. Following application of the ITO coatings, electrochromic layers were separately deposited onto the respective ITO coated and primed plastic substrates.
  • a tungsten oxide thin film was deposited on one substrate by direct current magnetron sputtering, and a nitrogen-containing iridium oxide thin film was deposited on the other substrate by direct current magnetron sputtering. Following these depositions, the IrOxNy/lTO/primer/polymer substrate was electrochemically charged (reduced) in 0.1 normal aqueous hydrochloric acid. The W0 3 /ITO/primer/polymer substrate was not electrochemically treated.
  • the monomer solution was then exposed to visible light through the W0 3 -coated substrate, thereby forming an AMPSA/DMA ion- conducting polymer which bonded the coated substrates of a laminated electrochromic device.
  • the light source which was situated about 7.5 cms below the monomer solutions, comprised four (4) 30 watt Phillips TLDK fluorescent tubes.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Nonlinear Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Inorganic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)

Abstract

L'invention concerne des polymères conducteurs d'ions utiles dans la préparation de dispositifs électro-optiques, qui sont préparés au moyen d'un système d'amorçage à base d'oxyde de triméthylbenzoyldiphényl phosphine.
PCT/US1999/014067 1998-06-22 1999-06-18 Dispositifs electro-optiques contenant des electrolytes reagissant a la lumiere visible Ceased WO1999067682A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU45823/99A AU4582399A (en) 1998-06-22 1999-06-18 Electrooptic devices containing visible-light initiated electrolytes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10238098A 1998-06-22 1998-06-22
US09/102,380 1998-06-22

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WO1999067682A1 true WO1999067682A1 (fr) 1999-12-29

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007005617A3 (fr) * 2005-06-30 2009-04-30 Univ California Colle polymere conductrice d'electricite, dispositifs et procedes de fabrication associes
US9083358B2 (en) 2004-08-30 2015-07-14 Micron Technology, Inc. Delay lock loop phase glitch error filter

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5471338A (en) * 1993-11-12 1995-11-28 Ppg Industries, Inc. Electrochromic device with plastic substrate
US5569683A (en) * 1995-05-22 1996-10-29 Thermedics, Inc. Gel compositions
US5859723A (en) * 1994-05-17 1999-01-12 Flachglas Ag Electrochromic pane arrangement

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5471338A (en) * 1993-11-12 1995-11-28 Ppg Industries, Inc. Electrochromic device with plastic substrate
US5859723A (en) * 1994-05-17 1999-01-12 Flachglas Ag Electrochromic pane arrangement
US5569683A (en) * 1995-05-22 1996-10-29 Thermedics, Inc. Gel compositions

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9083358B2 (en) 2004-08-30 2015-07-14 Micron Technology, Inc. Delay lock loop phase glitch error filter
WO2007005617A3 (fr) * 2005-06-30 2009-04-30 Univ California Colle polymere conductrice d'electricite, dispositifs et procedes de fabrication associes

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