WO2005015301A1 - Dispositif electrochromique a base de polymeres conducteurs, procede de production associe et produit ainsi obtenu - Google Patents

Dispositif electrochromique a base de polymeres conducteurs, procede de production associe et produit ainsi obtenu Download PDF

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Publication number
WO2005015301A1
WO2005015301A1 PCT/ES2004/000339 ES2004000339W WO2005015301A1 WO 2005015301 A1 WO2005015301 A1 WO 2005015301A1 ES 2004000339 W ES2004000339 W ES 2004000339W WO 2005015301 A1 WO2005015301 A1 WO 2005015301A1
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WIPO (PCT)
Prior art keywords
electrochromic
poly
polymer
conductive
device based
Prior art date
Application number
PCT/ES2004/000339
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English (en)
Spanish (es)
Inventor
David Mecerreyes Molero
José Adolfo POMPOSO ALONSO
Hans-Jurgen GRANDE TELLERÍA
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Fundacion Cidetec
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Publication of WO2005015301A1 publication Critical patent/WO2005015301A1/fr

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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
    • G02F1/1516—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
    • G02F1/15165—Polymers
    • 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

Definitions

  • the present invention relates to an electrochromic device based on conductive polymers constituted by a multilayer structure that allows controlling the level of transmittance and the color change of the material according to the applied potential.
  • the object of the invention is a device comprising a transparent substrate layer, a conductive polymer layer, an electrolyte, another conductive polymer layer and another transparent substrate layer, such that the conductive polymer acts as an electrochromic material and as a collector. of current at the same time.
  • the method of obtaining said device, as well as the product obtained from said device, is also an object of the invention.
  • electrochromic devices exist that take advantage of the ability of certain materials to exhibit color changes by changing their oxidation state. In this sense, these devices are, technologically, the basis of several applications that are already on the market such as anti-glare rearview mirrors and smart windows, which darken and lighten in a controlled way under the action of electric current.
  • a conventional electrochromic device is composed of a sandwich structure of up to seven layers of materials of which five are active and the other two are glass or plastic supports. The operation of these devices is based on the transport of protons or lithium cations from a storage layer to an electrochromic layer through an ion or electrolyte conductive layer.
  • the injection of ions into the electrochromic layer changes its optical properties, causing a change in the absorption spectrum and therefore color of the device.
  • the three central layers form a sandwich-type structure between two transparent plastics or glasses covered with my thin layer of an electrically conductive oxide, usually tin doped oxide with indium (ITO).
  • ITO indium
  • the electrochromic device that is recommended solves the problem described above in a satisfactory way in a way that allows preparing electrochromic devices that use an organic layer based on a conductive polymer that simultaneously acts as an electrochromic material and as a collector
  • the proposed invention greatly simplifies the construction of electrochromic devices, obtaining a three-layer electrochromic device of active materials, based on the use of a conductive polymer as an electrochromic material and as a current collector.
  • a conductive polymer can function as an ion storage layer and current collector, with the particularity that both electrodes are joined and separated by an electrolyte, preferably polymeric.
  • the procedure for obtaining said electrochromic devices is based on the following two stages:
  • the deposition stage of the conductive polymer on the transparent sheet of glass or plastic can be carried out by different methods. Among these methods stands out the deposition of a polymer solution or dispersion and formation of a film by evaporation of the solvent or casting. A film can also be prepared by immersing the substrate in a solution where the synthesis of the conductive polymer is carried out under suitable conditions to form a thin film on the substrate.
  • the second stage can be carried out in different ways, so that a film can be prepared by casting a solution of a polymer with a dissolved salt and that this film serves as an adhesive between the two outer sheets. Also, a film of a polymer electrolyte can be glued with the outer sheets by pressure, and another alternative would be to use a paper or plastic separator which is wetted from a liquid electrolyte.
  • conductive polymer used in the description of the invention includes polymers of the family of polypropyls, polythiophenes, polyvinylphenylene and polyanüins.
  • pyrrole, vinylphenylene, aniline or thiophene includes the unsubstituted monomer as well as the following substituted variants of said monomers: 3- alkyl, 3-aryl, 3,4-alkyl, 3,4-ethylenedioxy, 3,4-aryl, as well as n-alkyl and n-aryl; where "alkyl” denotes a straight or branched chain hydrocarbon radical and "ariF'a hydrocarbon radical of aromatic nature.
  • liquid electrolyte As for the term “liquid electrolyte”, this includes different electrolytic solutions that are formed by organic solvents with a dissolved salt. Such solvents are of the type ethylene carbonate, propylene carbonate, ⁇ -butyrolactone. Likewise, they can be solutions of ionic liquids such as imidazole salts, pyridinium salts or triethylammonium salts and / or mixtures of both.
  • polymer electrolyte refers to a mixture of a polymer with a dissolved salt.
  • Said polymer includes polymers such as poly (ethylene glycol), poly (propylene glycol), poly (ethylene oxide), copolymers of poly (ethylene oxide-co-epichloridrin), poly (propylene oxide), poly (alkyl methacrylate) and poly (alkyl acrylate).
  • the salt may be of the sodium chloride, lithium chloride, lithium perchlorate, lithium triflate type.
  • polymers can be used without the need for a polyelectrolyte-type dissolved salt such as poly (styrene sulfonate), poly (imidazoyl) chloride or bromide, poly (vinyl pyridine), and poly (amidopropyl sulfonate).
  • a polyelectrolyte-type dissolved salt such as poly (styrene sulfonate), poly (imidazoyl) chloride or bromide, poly (vinyl pyridine), and poly (amidopropyl sulfonate).
  • the electrochromic device of the present invention has excellent performance by being able to control the level of fransmittance and the color change of the material depending on the potential applied. It also exhibits excellent cycling behavior, highlighting its usefulness in applications such as flexible labels, electrochromic glasses, flexible screens, ultra-violet smart filters, iriff-red filters, windows and electrochromic mirrors.
  • Another advantage of the present invention is the possibility of obtaining a design or drawing on the devices by lithography by selectively degrading the active material (conductive polymer), being useful in the design of electrochromic images.
  • Figure 1 shows a schematic representation of a conventional electrochromic device that is part of the state of the art.
  • Figure 2.- Shows a schematic representation of the electrochromic device that is recommended,
  • the invention that is recommended simplifies the electrochromic devices (1), going from having a conventional seven-layer electrochromic device (1), according to figure 1, to obtaining an electrochromic device (1) based
  • the electrochromic device (1) that is recommended is constituted by a multilayer structure composed of a transparent substrate layer (3), a conductive polymer layer (2), an electrolyte (4), another conductive polymer layer (2) and another transparent substrate layer (3), so that the conductive polymer (2) acts as an electrochromic material and as a current collector at the same time, allowing the electrochromic device (1) to exhibit excellent performance by controlling the level of fransmittance and the color change of the material depending on the potential (5) applied.
  • conductive polymer (2) comprises polymers of the family of polypropyls, polythiophenes, polyvinylphenylene and polyanilines.
  • pyrrole, vinylphenylene, aniline or thiophene comprises the unsubstituted monomer as well as the following substituted variants of said monomers: 3-alkyl, 3-aryl, 3,4-alkyl, 3,4-ethylenedioxy, 3,4-aryl, as well as n-alkyl and n-aryl; where "alkyl” denotes a radical linear or branched chain hydrocarbon and "aryl" a hydrocarbon radical of aromatic nature.
  • liquid electrolyte (4) this comprises different electrolytic solutions that are formed by organic solvents with a dissolved salt.
  • solvents are of the type ethylene carbonate, propylene carbonate, ⁇ -butyrolactone.
  • ionic liquids such as imidazole salts, pyridinium salts or triethylammonium salts and / or mixtures of both.
  • polymeric electrolyte (4) refers to a mixture of a polymer with a dissolved salt.
  • Said polymer includes polymers such as poly (ethylene glycol), poly (propylene glycol), poly (ethylene oxide), copolymers of poly (ethylene oxide-co-epichloridrine), poly (propylene oxide), poly (alkyl methacrylate) and poly (alkyl acrylate).
  • the salt may be of the sodium chloride, lithium chloride, lithium perchlorate, lithium triflate type.
  • polymers can be used without the need for a polyelectrolyte-type dissolved salt such as poly (styrene sulfonate), poly (imidazoyl) chloride or bromide, poly (vinyl pyridine), and poly (amidopropyl sulfonate).
  • a polyelectrolyte-type dissolved salt such as poly (styrene sulfonate), poly (imidazoyl) chloride or bromide, poly (vinyl pyridine), and poly (amidopropyl sulfonate).
  • the procedure that is recommended for obtaining electrochromic devices (1) mainly comprises the following two stages:
  • the deposition step of the conductive polymer layers (2) on the transparent substrate layers (3) can be carried out by different methods. Between these Methods highlights the deposition of a polymer solution or dispersion and formation of a film by evaporation of the solvent or casting.
  • a fihne can also be prepared by immersion of the transparent substrate (3) in a solution where the synthesis of the conductive polymer (2) is carried out under conditions suitable for forming a thin film on the fransparent substrate (3).
  • the second stage of joining the conductive polymer layers (2) can be carried out in different ways, so that a film can be prepared by casting a solution of a polymer with a dissolved salt and that this film serves as an adhesive between The two outer sheets. Also, you can paste a film of an electrolyte
  • products obtained from said procedure or said device are recommended, highlighting its usefulness in applications such as flexible labels, electrochromic glasses, flexible screens, ultra-violet smart filters, inffa-red filters, windows, electrochromic mirrors or applications related to The design of electrochromic images.
  • An electrochromic reference device (1) was prepared from poly (ethylene terephthalate) sheets coated with a transparent electrically conductive oxide (ITO). These sheets are commercial by the company Shieldal (USA). Thus, on a sheet of poly (ethylene terephthalate) coated with ITO (3cm 2 ) a film was prepared by depositing a solution of poly (ethylene dioxythiophene) marketed under the name of Bayfron (Bayer) after which it was allowed to dry. The other electrode was my ITO coated sheet in which a polypyrrole film was deposited by electropolymerization. The electropolymerization was carried out in an aqueous solution containing lithium perchlorate and using a constant potential (5) of 0.7 volts
  • the polypyrrole electrode was adhered by pressing lightly to form a sandwich structure.
  • Said electrochromic device (1) showed a color change between yellow to dark blue-black when changing the potential (5) between -1.5 N and 1.5 N. The color change occurred in ⁇ 10 seconds. The maximum change in fransmittance was between 70 and 45%.
  • the electrochromic devices (1) presented poor cyclability when losing their activity after 20 cycles or several days (3 days) after their assembly.
  • a simplified electrochromic device (1) was prepared from sheets of poly (ethylene 'terephthalate) coated the conductive polymer, (2) poly (ethylenedioxythiophene). These sheets are commercial under the ORGACON brand (Agfa, Belgium).
  • Orgacon EL 350 (3cm 2 ) my film was prepared by depositing a solution of lithium perchlorate (0.015 grams) and poly (ethylene oxide-co-epichloridrine) (Daiso Co. EM-2 (22)) ( 0.7 grams) in tetrahydrofuran (5 milliliters). After drying the solvent at room temperature for 2 hours another layer of Orgacon EL350 was adhered by pressing on the first slightly, forming a sandwich structure.
  • This device showed a color change between light blue transparent to dark blue when changing the potential (5) between 0 and 3 V.
  • the color change occurred in ⁇ 10 seconds.
  • the maximum change in transmittance was between 55 and 40%.
  • the electrochromic devices (1) remained active after 5000 cycles of 1 minute duration between 0 and 3 N.
  • a sandwich structure was prepared by applying a pressure of 2 bars for 1 minute on a sandwich prepared with Orgacon El-4500 sheet, poly (sodium styrene sulfonate) film and Orgacon El-4500 sheet.
  • This device showed a color change between light blue transparent to dark blue when changing the potential (5) between 0 and 3 N.
  • the maximum change in transmittance was between 70 and 60%.
  • the color change occurred in ⁇ 10 seconds.
  • the electrochromic devices (1) remained active for 5000 cycles of 1 minute duration between 0 and 3 N.
  • a sandwich structure was prepared using 3-ethyl-l-methyl imidazoyl bromide as an adhesive between 2 sheets of Orgacon EL 350.
  • Said electrochromic device (1) showed a color change between light blue transparent to dark blue when changing the potential ( 5) between 0 and 3 N.
  • the maximum change in transmittance was between 57% and 40%. The color change took place in ⁇ 5 seconds.
  • the electrochromic devices (1) are still active for 5000 cycles of 1 minute duration between 0 and 3 N.
  • the conductive poly (ethylene dioxythiophene) polymer was deposited by casting its commercial solution (Baytron P, Bayer) on two glasses (5 cm x 5 cm).
  • a polymer electrolyte film was prepared by depositing a solution of lithium perchlorate (0.015 grams) and poly (ethylene oxide-co-epichloridrine) (0.7 grams) in tetrahydrofuran (5 milliliters) on the poly (ethylene dioxythiophene) layer of one of the glasses. After drying the solvent at room temperature for 2 hours, it was adhered to the coating of the other glass by pressing lightly to form a sandwich structure. This device showed a color change between light blue fransparente to dark blue when changing the potential (5) against 0 and 3 N. The maximum change in transmittance was between 35 and 20%.
  • the electrochromic devices (1) were still active for 5000 cycles of 1 minute duration between 0 and 3 N.
  • An electrochromic device (1) similar to example 1 was prepared by depositing the polymer electrolyte from a solution of lithium perchlorate (0.015 grams), poly (ethylene oxide-co-epichloridrine) (0.7 grams) in tetrahydrofuran (5 milliliters). After drying the solvent at room temperature for 2 hours another layer of Orgacon EL350 was adhered by pressing lightly to form a sandwich structure.
  • Said electrochromic device (1) showed a drawing that remains colorless while it presented a color change in front of light blue transparent to dark blue when changing the potential (5) between 0 and 3 N, in the non-lithographed area.
  • the maximum change in transmittance was between 55 and 40%.
  • the electrochromic devices (1) were still active for 5000 cycles of 1 minute duration between 0 and 3 N.
  • a fransparent sheet of poly (ethylene terephthalate) (APLI photocopier fransparency) was introduced into a solution of ammonium persulfate (2.54 grams) in the presence of poly (vinyl pyrrolidone) (2 grams) in water (100 ml). An aqueous solution of pyrrole (1.5 grams) was added 10 ml and the sheet was removed after 15 minutes.
  • a film was deposited by depositing a solution of lithium perchlorate (0.015 grams) and poly (ethylene oxide-co-epichloridrine) (0.7 grams) in tetrahydrofuran (5 milliliters). After drying the solvent at room temperature for 2 hours another layer of Orgacon EL350 was adhered by pressing lightly to generate a sandwich structure.
  • Said electrochromic device (1) presented a color change against blue-black to yellow when the potential (5) changed between -1.5 and 1.5 N.
  • the color change occurred in ⁇ 10 seconds.
  • the maximum change in transmittance was between 30% and 55%.

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  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)

Abstract

L'invention concerne un dispositif électrochromique (1) qui est constitué d'une structure multicouche composée d'une couche de substrat transparent (3), d'une couche de polymère conducteur (2), d'un électrolyte (4), d'une autre couche de polymère conducteur (2) et d'une autre couche de substrat transparent (3), de sorte que le polymère conducteur (2) agit en même temps comme un matériau électrochromique et comme un collecteur de courant. Ainsi, le dispositif électrochromique (1) présente d'excellentes performances qui lui permettent de régler le niveau de transmittance et le changement de couleur du matériau en fonction du potentiel (5) appliqué.
PCT/ES2004/000339 2003-08-05 2004-07-20 Dispositif electrochromique a base de polymeres conducteurs, procede de production associe et produit ainsi obtenu WO2005015301A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ESP200301884 2003-08-05
ES200301884A ES2223289B1 (es) 2003-08-05 2003-08-05 Dispositivo electrocromico basado en polimeros conductores, el procedimiento de obtencion del mismo, asi como el producto obtenido.

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WO2005015301A1 true WO2005015301A1 (fr) 2005-02-17

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011001418A1 (fr) 2009-07-03 2011-01-06 L'oreal Article cosmétique possédant une structure multicouche électrochromique
WO2011001417A1 (fr) 2009-07-03 2011-01-06 L'oreal Article cosmétique possédant une structure multicouche électrochromique
WO2011001415A1 (fr) 2009-07-03 2011-01-06 L'oreal Article cosmétique comprenant une structure multicouche électrochromique
WO2011001416A1 (fr) 2009-07-03 2011-01-06 L'oreal Article cosmétique possédant une structure multicouche électrochromique

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5737114A (en) * 1991-01-31 1998-04-07 Eveready Battery Company, Inc. Label having an incorporated electrochromic state-of-charge indicator for an electrochemical cell
US6175441B1 (en) * 1998-03-13 2001-01-16 Heuer Electrochromic device based on poly-(3,4-dioxy-thiopene) derivatives
WO2002075441A2 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique et compositions utilisees pour fabriquer de tels dispositifs
US20020134980A1 (en) * 2001-03-07 2002-09-26 Marten Armgarth Electrochemical pixel device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5737114A (en) * 1991-01-31 1998-04-07 Eveready Battery Company, Inc. Label having an incorporated electrochromic state-of-charge indicator for an electrochemical cell
US6175441B1 (en) * 1998-03-13 2001-01-16 Heuer Electrochromic device based on poly-(3,4-dioxy-thiopene) derivatives
US20020134980A1 (en) * 2001-03-07 2002-09-26 Marten Armgarth Electrochemical pixel device
WO2002075441A2 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique et compositions utilisees pour fabriquer de tels dispositifs

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011001418A1 (fr) 2009-07-03 2011-01-06 L'oreal Article cosmétique possédant une structure multicouche électrochromique
WO2011001417A1 (fr) 2009-07-03 2011-01-06 L'oreal Article cosmétique possédant une structure multicouche électrochromique
WO2011001415A1 (fr) 2009-07-03 2011-01-06 L'oreal Article cosmétique comprenant une structure multicouche électrochromique
WO2011001416A1 (fr) 2009-07-03 2011-01-06 L'oreal Article cosmétique possédant une structure multicouche électrochromique
US8863759B2 (en) 2009-07-03 2014-10-21 L'oreal Cosmetic article including an electrochromic multilayer structure

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Publication number Publication date
ES2223289A1 (es) 2005-02-16
ES2223289B1 (es) 2006-04-16

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