WO2022181760A1 - 調光材料、調光フィルム、及び調光デバイス - Google Patents

調光材料、調光フィルム、及び調光デバイス Download PDF

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WO2022181760A1
WO2022181760A1 PCT/JP2022/007843 JP2022007843W WO2022181760A1 WO 2022181760 A1 WO2022181760 A1 WO 2022181760A1 JP 2022007843 W JP2022007843 W JP 2022007843W WO 2022181760 A1 WO2022181760 A1 WO 2022181760A1
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light
light modulating
electrode
modulating material
light control
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PCT/JP2022/007843
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English (en)
French (fr)
Japanese (ja)
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弘司 福井
幹敏 末松
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積水化学工業株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C08K5/053—Polyhydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C08L25/04—Homopolymers or copolymers of styrene
    • C08L25/06—Polystyrene
    • 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
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • 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
    • 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
    • G02F1/1516—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 organic material

Definitions

  • the present invention relates to an electrochromic light control material capable of controlling the transmittance of light in a specific wavelength range, and a light control film and a light control device using the light control material.
  • Electrochromic light control materials that can control the transmittance of light in a specific wavelength range are intended to adjust the transmittance by blocking light of a specific wavelength, and to adjust the color tone. It's being used. Such dimming materials are widely used in various applications such as interior members, building members, and electronic components.
  • Patent Document 1 For example, in Patent Document 1 below, a laminate in which three layers of an electrochromic layer of nickel oxide, an ion-conducting layer, and an electrochromic layer of tungsten oxide are sequentially laminated is sandwiched between two conductive substrates. An electrochromic dimming device is disclosed. Patent Document 1 describes that an electrochromic layer of nickel oxide or tungsten oxide is formed by a vapor deposition method or a sputtering method.
  • Patent Document 2 discloses a layer containing a conductive electrochromic polydioxythiophene, a layer containing an electrolyte containing protonic acid, and a layer containing an ion-retaining compound or a mixture of ion-retaining compounds.
  • An electrochromic device is disclosed having a layered structure.
  • JP-A-2004-062030 Japanese translation of PCT publication No. 2002-526801
  • Patent Document 2 when an electrochromic material made of a conductive polymer such as polythiophene is used, it is difficult to apply without using an organic solvent, which is undesirable from an environmental point of view.
  • An object of the present invention is to provide a light modulating material that can be easily formed into a film by coating in an aqueous system and that can control the light transmittance in a wide range from visible light to infrared light by applying a voltage. and a light control film and a light control device using the light control material.
  • the light modulating material according to the present invention contains at least one of polystyrenesulfonic acid and polystyrenesulfonic acid derivatives.
  • the polystyrenesulfonic acid derivative is polystyrenesulfonate.
  • the polystyrenesulfonate is sodium polystyrenesulfonate.
  • the light modulating material according to the present invention further contains a water-soluble plasticizer.
  • the water-soluble plasticizer is glycerin.
  • the light modulating material according to the present invention does not substantially contain polythiophene.
  • a light control film according to the present invention includes a light control material configured according to the present invention.
  • a light modulating device comprises a first electrode, an electrolyte layer provided on the first electrode, and a light modulating material provided on the electrolyte layer and constructed according to the present invention. and a second electrode provided on the light modulating material layer.
  • the first electrode is a working electrode
  • the second electrode is a counter electrode
  • the light modulating material is disposed on the counter electrode side of the electrolyte layer. layers are provided.
  • a light modulating material that can be easily formed into a film by coating in an aqueous system and that can control the light transmittance in a wide range from visible light to infrared light by applying a voltage. and a light control film and a light control device using the light control material.
  • FIG. 1 is a schematic front cross-sectional view showing a light control device according to one embodiment of the present invention.
  • FIG. 2 is a schematic front cross-sectional view showing the light control device produced in Example 1.
  • FIG. 3 is a graph showing transmission spectra of the light modulating device of Example 1 when a voltage of 0 V to 3.0 V is applied.
  • FIG. 4 is a diagram showing transmission spectra when a voltage is applied while changing from 0 V to 3.0 V in the light control device of Reference Example 1.
  • FIG. 1 is a schematic front cross-sectional view showing a light control device according to one embodiment of the present invention.
  • FIG. 2 is a schematic front cross-sectional view showing the light control device produced in Example 1.
  • FIG. 3 is a graph showing transmission spectra of the light modulating device of Example 1 when a voltage of 0 V to 3.0 V is applied.
  • FIG. 4 is a diagram showing transmission spectra when a voltage is applied while changing from 0 V to 3.0 V in the light
  • the light modulating material of the present invention contains at least one of polystyrenesulfonic acid and polystyrenesulfonic acid derivatives. Therefore, the light modulating material of the present invention may contain either polystyrenesulfonic acid or polystyrenesulfonic acid derivative alone, or may contain both polystyrenesulfonic acid and polystyrenesulfonic acid derivative.
  • the light modulating material of the present invention contains at least one of polystyrenesulfonic acid and a polystyrenesulfonic acid derivative, it can be easily formed into a film by coating in an aqueous system, and furthermore, by applying a voltage, it can be converted from visible light to It is possible to control light transmittance in a wide range up to infrared light.
  • inorganic materials such as nickel oxide and tungsten oxide, and conductive polymers such as polythiophene have been known as electrochromic light control materials.
  • light modulating materials using inorganic materials are often formed by vapor deposition or sputtering, which requires a large-scale apparatus such as a chamber, which is undesirable in terms of manufacturing costs.
  • conductive polymers such as polythiophene are often difficult to dissolve in water, it is difficult to apply them unless an organic solvent is used, which is undesirable from an environmental point of view.
  • polystyrene sulfonic acid and polystyrene sulfonic acid derivatives exhibit electrochromic properties and can be used as light modulating materials. That is, the present inventors have found that by applying a voltage to polystyrene sulfonic acid or a polystyrene sulfonic acid derivative itself, it is possible to control light transmittance in a wide range from visible light to infrared light.
  • polystyrene sulfonic acid and polystyrene sulfonic acid derivatives such as polystyrene sulfonate have high solubility in water, they can be easily formed into films by coating in an aqueous system. Therefore, it is excellent in handleability and does not require a large-scale apparatus such as a chamber as in the vapor deposition method or the sputtering method, so that the manufacturing cost can be reduced.
  • coating can be performed without using an organic solvent, it can be used favorably from an environmental point of view.
  • the polystyrene sulfonate is not particularly limited, and for example, sodium polystyrene sulfonate, lithium polystyrene sulfonate, ammonium polystyrene sulfonate, and the like can be used. Among them, it is preferable to use sodium polystyrene sulfonate, which is highly versatile, as the polystyrene sulfonate.
  • polystyrene sulfonic acid derivatives other than polystyrene sulfonate may be used as long as they are water-soluble.
  • examples of polystyrenesulfonic acid derivatives other than polystyrenesulfonate include polyparamethylstyrenesulfonic acid, copolymers of styrenesulfonic acid and styrene, copolymers of styrenesulfonate and maleic anhydride, styrenesulfonates and A copolymer of maleimide anhydride, a copolymer of styrenesulfonic acid and (meth)acrylic acid ester, and the like can be mentioned.
  • (meth)acryl means methacryl or acryl.
  • the polystyrenesulfonic acid derivative may be a copolymer of styrenesulfonic acid or styrenesulfonate and other water-soluble monomers.
  • copolymers include styrenesulfonic acid-sodium styrenesulfonate copolymer, styrenesulfonic acid-lithium styrenesulfonate copolymer, styrenesulfonic acid-potassium styrenesulfonate copolymer, and styrenesulfonic acid-styrene.
  • a calcium sulfonate copolymer, a styrenesulfonic acid-ammonium styrenesulfonate copolymer, and the like are included.
  • polystyrene sulfonic acid derivatives may be used singly or in combination.
  • the weight average molecular weight (Mw) of polystyrenesulfonic acid or polystyrenesulfonic acid derivative is not particularly limited, but is preferably 2,000 or more, more preferably 10,000 or more, still more preferably 50,000 or more, and particularly preferably 200,000 or more. 000 or more, most preferably 500,000 or more, preferably 2,000,000 or less, more preferably 1,500,000 or less.
  • the weight average molecular weight (Mw) indicates the weight average molecular weight in terms of sodium polystyrene sulfonate measured by gel permeation chromatography (GPC).
  • the content of at least one of polystyrenesulfonic acid and polystyrenesulfonic acid derivatives is preferably 10% by mass or more, more preferably 30% by mass or more, and still more preferably 40% by mass or more, relative to the entire light modulating material. , preferably 90% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less, and particularly preferably 60% by mass or less.
  • the content of at least one of the polystyrene sulfonic acid and the polystyrene sulfonic acid derivative is equal to or higher than the above lower limit, the light transmittance in a wide range from visible light to infrared light can be further effectively increased by applying a voltage. can be controlled to However, the upper limit of the content of at least one of the polystyrenesulfonic acid and the polystyrenesulfonic acid derivative is not particularly limited, and may be 100% by mass with respect to the entire light modulating material.
  • the light modulating material of the present invention preferably does not substantially contain a light modulating material different from polystyrene sulfonic acid and polystyrene sulfonic acid derivatives.
  • the photochromic material does not substantially contain a poorly water-soluble light modulating material.
  • dimming materials include, for example, polythiophene, polyaniline, polyvinylpyridine, and the like. In this case, water-based coating can be performed more favorably.
  • the expression "substantially does not contain” means, for example, that the content is 5% by mass or less with respect to the entire light modulating material. However, it does not have to contain any dimming material that is difficult to dissolve in water.
  • the light modulating material of the present invention preferably contains a plasticizer in addition to at least one of polystyrenesulfonic acid and polystyrenesulfonic acid derivatives.
  • a plasticizer in addition to at least one of polystyrenesulfonic acid and polystyrenesulfonic acid derivatives.
  • the plasticizer is preferably a water-soluble plasticizer. In this case, coatability can be further improved.
  • water-soluble plasticizers include, but are not limited to, polyoxyalkylenes such as glycerin, polyethylene glycol, polypropylene glycol, copolymers of polyethylene glycol and polypropylene glycol, N-methylpyrrolidone, trimethylolpropane, sucrose, and sorbitol. , or xylitol or the like can be used. These may be used individually by 1 type, and may use multiple types together. Among them, it is preferable to use glycerin as the water-soluble plasticizer. In this case, electrons can be more easily moved when a voltage is applied, and light transmittance in a wide range from visible light to infrared light can be more effectively controlled.
  • polyoxyalkylenes such as glycerin, polyethylene glycol, polypropylene glycol, copolymers of polyethylene glycol and polypropylene glycol, N-methylpyrrolidone, trimethylolpropane, sucrose, and sorbitol.
  • the content of the plasticizer is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, and particularly preferably 40% by mass or more, relative to the entire light modulating material. is 60% by mass or less, more preferably 50% by mass or less.
  • the light transmittance in a wide range from visible light to infrared light can be controlled more effectively by applying voltage.
  • FIG. 1 is a schematic front cross-sectional view showing a light control device according to one embodiment of the present invention.
  • the light modulating device 1 includes a first electrode 2 , a second electrode 3 , an electrolyte layer 4 and a light modulating material layer 5 .
  • an electrolyte layer 4 is provided on the first electrode 2 .
  • a light modulating material layer 5 is provided on the electrolyte layer 4 .
  • a second electrode 3 is provided on the light modulating material layer 5 .
  • first electrode 2 and the second electrode 3 for example, transparent electrodes such as ITO can be used.
  • the first electrode 2 and the second electrode 3 may be made of the same material or may be made of different materials.
  • the first electrode 2 and the second electrode 3 may be conductive films provided on a support such as a glass substrate.
  • the electrolyte layer 4 may be composed of an electrolyte solution, or may be composed of a solid electrolyte.
  • the electrolyte solution is not particularly limited, for example, an electrolyte solution containing LiPF 6 or the like in a solvent such as ethylene carbonate (EC), dimethyl carbonate (DMC), or propylene carbonate (PC) can be used.
  • EC ethylene carbonate
  • DMC dimethyl carbonate
  • PC propylene carbonate
  • the light control material layer 5 is a light control film containing the light control material of the present invention described above.
  • the light modulating material layer 5 can be formed, for example, by coating an aqueous solution containing the light modulating material on the second electrode 3 by a coating method such as spin coating.
  • the light transmittance at each wavelength changes.
  • a voltage is applied so that the first electrode 2 is the working electrode (reduction side, positive electrode) and the second electrode 3 is the counter electrode (oxidation side, negative electrode). . Therefore, in this embodiment, the light modulating material layer 5 is provided on the opposite electrode side of the electrolyte layer 4 .
  • a light modulating material layer using polythiophene or the like as a light modulating material is provided on the working electrode side with respect to the electrolyte layer.
  • the present inventors have found that the light modulating material layer 5 using polystyrene sulfonic acid or a polystyrene sulfonic acid derivative as the light modulating material is provided on the counter electrode side of the electrolyte layer 4 rather than on the working electrode side. It was found that electrochromic properties were expressed by
  • the light control device 1 can be obtained by simply forming the light control material layer 5 by coating with a water system.
  • the light control device 1 can control light transmittance in a wide range from visible light to infrared light by applying a voltage.
  • Example 1 the light control device 21 shown in FIG. 2 was produced. Specifically, first, a first electrode 22 and a second electrode 23 each having a conductive film made of ITO provided on a glass substrate were prepared.
  • a light modulating material containing 50% by mass of sodium polystyrene sulfonate manufactured by Tosoh Finechem, product number “PS-100”, weight average molecular weight: 800,000 to 1,200,000
  • PSD100 weight average molecular weight: 800,000 to 1,200,000
  • glycerin 50% by mass of glycerin.
  • the light modulating material was dispersed in water by applying ultrasonic waves for 30 minutes to obtain a dispersion.
  • the dispersion was applied onto the second electrode 23 by spin coating. Then, it was dried by heating at 100° C. for 1 hour, and the light modulating material layer 25 was produced.
  • Example 1 the first electrode 22 and the second electrode 23 were pasted together with a pressure-sensitive tape via two strip-shaped supporting members 26 and 27 .
  • an electrolyte solution LiPF 6 . . . 1 mol/L, solvent .
  • an epoxy adhesive was applied to the periphery and cured at 50° C. for 1 hour to seal the inside.
  • the light control device 21 shown in FIG. 2 was obtained.
  • the first electrode 22 was used as the working electrode
  • the second electrode 23 was used as the counter electrode.
  • the light modulating material layer 25 is provided on the counter electrode side of the electrolyte layer 24 .
  • Example 2 As a light control material, sodium polystyrene sulfonate (manufactured by Tosoh Finechem Co., Ltd., product number “PS-100”, weight average molecular weight: 800,000 to 1,200,000) 100% by mass without using glycerin.
  • a light modulating material layer 25 and a light modulating device 21 were obtained in the same manner as in Example 1, except that the materials were used.
  • Example 3 A light control material containing 90% by mass of sodium polystyrene sulfonate (manufactured by Tosoh Finechem Co., Ltd., product number “PS-100”, weight average molecular weight: 800,000 to 1,200,000) and 10% by mass of glycerin as a light control material.
  • a light modulating material layer 25 and a light modulating device 21 were obtained in the same manner as in Example 1, except that the materials were used.
  • Example 4 A light control material containing 70% by mass of sodium polystyrene sulfonate (manufactured by Tosoh Finechem Co., Ltd., product number “PS-100”, weight average molecular weight: 800,000 to 1,200,000) and 30% by mass of glycerin as a light control material.
  • a light modulating material layer 25 and a light modulating device 21 were obtained in the same manner as in Example 1, except that the materials were used.
  • Example 5 A light modulating material layer 25 and a light modulating device were prepared in the same manner as in Example 1, except that polyethylene glycol (manufactured by Sanyo Chemical Industries, Ltd., product number “PED-600”, number average molecular weight: 600) was used instead of glycerin. 21 was obtained.
  • polyethylene glycol manufactured by Sanyo Chemical Industries, Ltd., product number “PED-600”, number average molecular weight: 600
  • Example 6 A light modulating material layer 25 and a light modulating device 21 were obtained in the same manner as in Example 1, except that trimethylolpropane (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of glycerin.
  • Example 7 Polystyrene sulfonic acid (manufactured by Sigma Aldrich, 18% aqueous solution, weight average A light modulating material layer 25 and a light modulating device 21 were obtained in the same manner as in Example 1, except for using a molecular weight of 75,000.
  • Example 8 Ammonium polystyrene sulfonate (Sigma Aldrich), which is an ammonium salt of polystyrene sulfonate, instead of sodium polystyrene sulfonate (manufactured by Tosoh Finechem Co., Ltd., product number “PS-100”, weight average molecular weight: 800,000 to 1,200,000) A light control material layer 25 and a light control device 21 were obtained in the same manner as in Example 1, except that 30% aqueous solution, weight average molecular weight: 200,000) was used.
  • Example 9 Sodium polystyrene sulfonate (manufactured by Tosoh Finechem Co., Ltd., product number "PS-100", weight average molecular weight: 800,000 to 1,200,000) instead of polystyrene sulfonic acid, which is a lithium hydroxide neutralized salt of polystyrene sulfonic acid A light modulating material layer 25 and a light modulating device 21 were obtained in the same manner as in Example 1, except that lithium was used.
  • PS-100 weight average molecular weight: 800,000 to 1,200,000
  • the lithium polystyrene sulfonate used was prepared by neutralizing polystyrene sulfonic acid (manufactured by Sigma Aldrich, 18% aqueous solution, weight average molecular weight: 75,000) with an aqueous solution of lithium hydroxide.
  • Reference Example 1 In Reference Example 1, a light modulating device 21 similar to that of Example 1 was produced, and the second electrode 23 was used as the working electrode, and the first electrode 22 was used as the counter electrode. Therefore, in Reference Example 1, the light modulating material layer 25 is provided on the working electrode side of the electrolyte layer 24 .
  • a DC voltage was applied to the light control device, and changes in light transmittance were evaluated. Changes in light transmittance were measured using a JASCO spectrometer (model number: V-670). The applied voltage was 0 V to 3.0 V (CV), and the measurement was performed in an air atmosphere. Also, the measurement wavelength range was set to 2500 nm to 300 nm.
  • FIG. 3 is a diagram showing the transmission spectrum of the light control device of Example 1 when the voltage is applied while changing from 0V to 3.0V.
  • FIG. 4 is a diagram showing transmission spectra when a voltage is applied while changing from 0 V to 3.0 V in the light control device of Reference Example 1.
  • the transmittance is reduced over the entire visible light region and the infrared region after voltage application.
  • the light control material layer 25 on the counter electrode side of the electrolyte layer 24, the above electrochromic characteristics are exhibited.
  • Examples 2 to 9 transmission spectra were obtained before voltage application (applied voltage of 0 V), applied voltage of 2.5 V, and applied voltage of 3.0 V, respectively. From the obtained transmission spectrum, the difference in transmittance at a wavelength of 800 nm and a wavelength of 1300 nm was obtained before and after applying a voltage of 2.5 V and a voltage of 3.0 V, respectively. The results are shown in Table 1 below. In addition, in Table 1, the content of each material is the content when the entire light modulating material is 100% by mass. Further, the difference in light transmittance is the difference between the transmittance before voltage application (applied voltage 0 V) and the transmittance when voltages of 2.5 V and 3.0 V are applied (before voltage application - after voltage application).

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PCT/JP2022/007843 2021-02-26 2022-02-25 調光材料、調光フィルム、及び調光デバイス WO2022181760A1 (ja)

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JPS62186231A (ja) * 1986-02-12 1987-08-14 Toyo Soda Mfg Co Ltd エレクトロクロミツク表示材料
JPH07301708A (ja) * 1994-04-28 1995-11-14 Asahi Glass Co Ltd カラーフィルター付き基板及びその製造方法並びにそれを用いた液晶表示素子
JP2004526195A (ja) * 2001-03-07 2004-08-26 アクレオ アーベー エレクトロクロミックデバイス
JP2005519316A (ja) * 2002-03-07 2005-06-30 アクレオ アーベー 電気化学デバイス
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JPS59217791A (ja) * 1983-05-25 1984-12-07 Japan Electronic Ind Dev Assoc<Jeida> エレクトロクロミツク材料
JPS62186231A (ja) * 1986-02-12 1987-08-14 Toyo Soda Mfg Co Ltd エレクトロクロミツク表示材料
JPH07301708A (ja) * 1994-04-28 1995-11-14 Asahi Glass Co Ltd カラーフィルター付き基板及びその製造方法並びにそれを用いた液晶表示素子
JP2004526195A (ja) * 2001-03-07 2004-08-26 アクレオ アーベー エレクトロクロミックデバイス
JP2005519316A (ja) * 2002-03-07 2005-06-30 アクレオ アーベー 電気化学デバイス
US20190324341A1 (en) * 2018-04-19 2019-10-24 Gentex Corporation Plastic coatings for improved solvent resistance

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Title
KIMURA, KENICHI, KUMAR, JAYANT: "Electrochromism of Polyaniline/Poly (4-styrenesulfonate) Complex", JOURNAL OF PRINTING SCIENCE AND TECHNOLOGY, JAPANESE SOCIETY OF PRINTING SCIENCE AND TECHNOLOGY, JP, vol. 41, no. 2, 30 April 2004 (2004-04-30), JP , pages 109 - 116, XP009539242, ISSN: 0914-3319, DOI: 10.11413/nig.41.109 *

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