University of Washington

Chunye Xu

Minoru Taya

Lu Liu

Susan E Legenski

Chao Ma

Yasuo Kuga

Jin Wang

Green electrochromic (EC) materials based on thiophene, and a green EC material based on pyrazine are disclosed. A first thiophene derivative (2,3-Di-thiophen-2-yl-thieno[3,4-b]pyrazine), which was previously investigated as a nonlinear optical material, is here disclosed for its use as an EC material and for its incorporation into an EC device. Synthesis of two new thiophene derivatives (2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene and 2,5-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene), and a new pyrazine derivative (2,3-dibenzyl-5,7-di(thien-2-yl) thieno[3,4-b]pyrazine) are also disclosed, since these materials are all able to selectively change state to appear a green color and can be polymerized to achieve a green EC polymer.

Electrochromic materials

Eyewear exhibiting a variable light transmittance functionality is achieved by including a smart lens incorporating an electrochromic (EC) polymer, switchable between a first state and a second state in response to a voltage selectively applied thereto. The smart eyewear includes the smart lens, a voltage source, and a support. The EC polymer transmits more light in the first state than in the second state, because changing the state of the EC polymer varies the light transmittance of the smart lens. The voltage source is configured to provide the voltage required to switch the EC polymer between the first state and the second state, while the support member is configured to support the smart lens and enable a user to wear the smart eyewear. Embodiments can include sensors and controllers to automate the switching, as well as energy harvesting elements to increase battery life.

Smart sunglasses, helmet faceshields and goggles based on electrochromic polymers

A flexible electrochromic (EC) panel that is usable for a display device or for other applications in which at least a region of the panel is selectively caused to change opacity. An exemplary EC panel includes an electrochromic working layer or electrode formed of a PProDOT-Mepolymer film that is deposited on an indium tin oxide (ITO)-coated polyethylene terephthalate (PET) flexible substrate. Similarly, a counter electrode is formed by depositing a vanadium oxide-titanium oxide (VO&#x2014;TiO) composite film on another ITO PET coated flexible substrate. An ultraviolet light-cured film sealant is employed to seal the flexible panel and also serves as a spacer between the working and counter electrodes. The film sealant is patterned to define a volume for injecting an electrolyte solution through an inlet port provided in the film sealant. The inlet port is then closed. The EC panel can readily be flexed without damage.

Flexible panel based on electrochromic polymers

An electroactive polymer is used to produce a tactile sensor. The electroactive polymer (EAP) includes a sheet of an ion-exchange membrane having opposite surfaces on which are plated gold electrodes. The EAP is formed to have a dome-shape with a plurality of sensing electrodes circumferentially disposed around an outer surface of the dome. A flexible polymer underlying the EAP supports it and prevents a force applied to the tactile sensor from inverting the dome. The sensor electrodes produce separate output signals indicative of different vector components of an applied force acting on the tactile sensor, so that a direction of the force can be determined. Vias provided in the electrodes are electrically coupled to a flexible circuit that conveys the output signals externally from the sensing electrodes for use and further processing. A plurality of the tactile sensors can be formed as an array on an ion-exchange membrane.

Tactile sensors

Green electrochromic (EC) materials based on thiophene, and a green EC material based on pyrazine are disclosed. A first thiophene derivative (2,3-Di-thiophen-2-yl-thieno[3,4-b]pyrazine), which was previously investigated as a nonlinear optical material, is here disclosed for its use as an EC material and for its incorporation into an EC device. Synthesis of two new thiophene derivatives (2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene and 2,5-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene), and a new pyrazine derivative (2,3-dibenzyl-5,7-di(thien-2-yl)thieno[3,4-b]pyrazine) are also disclosed, since these materials are all able to selectively change state to appear a green color and can be polymerized to achieve a green EC polymer.

Green electrochromic materials

Devices including EC monomers polymerized using chronoamperometry to deposit a very thin homogeneous layer followed by cyclic voltammetry to increase the density of the EC polymer film. Another aspect of the present invention is directed to specific web like configurations for a grid of conductive material deposited onto a transparent substrate. The web like configuration is based either on concentric circles, or on concentric ellipses. Yet another aspect of the present invention is directed to an imaging system including a digital window that is disposed between a prism and a patterned analytic layer.

Electropolymerization of enhanced electrochromic (EC) polymer film

Syntheses of a new blue EC monomer (ProDOT-MePro), and a new red EC monomer (ProDOP-Et2) are described. Two additional new types of EC monomers based on 3,4-alkylenedioxythiophene include fluorinated EC monomers and an EC monomer including silicon. EC polymer devices having more than one different color EC polymer to enable additional colors to be provided using subtractive color mixing are also described, as well as EC polymer devices incorporating a logo, image, or text, are generally obscured when the device is colored, but become visible when the device is not colored. Also described are EC polymer devices that include a cathodic EC polymer layer, a gel electrolyte, a counter electrode, and a reference electrode. Working prototypes of such devices exhibit significant increases in the speed of transition of the EC device from a colored state to a transparent state.

Switchable window based on electrochromic polymers

Electrochromic monomers and polymers for a switchable window

Electropolymerization of EC monomers is employed to obtain an EC polymer film deposited on a substrate. A first embodiment of a method to produce the film employs cyclic voltammetry alone, while a second embodiment deposits a very thin homogeneous layer using chronoamperometry, and then cyclic voltammetry is employed to increase the density of the film. Another aspect of the present invention is directed to specific web like configurations for a grid of conductive material deposited onto a transparent substrate. The web like configuration is based either on concentric circles, or on concentric ellipses. Yet another aspect of the present invention is directed to an imaging system including a digital window that is disposed between a prism and a patterned analytic layer.

Three green EC materials based on thiophene, and a green EC material based on pyrazine are disclosed. A first thiophene derivative (2,3-Di-thiophen-2-yl-thieno[3,4-b]pyrazine), which was previously investigated as a nonlinear optical material, is here disclosed for its use as an EC material, and for its incorporation into an EC device. Synthesis of two new thiophene derivatives (2,5-di(thien-2-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene and 2,5-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-3,4-di(2,2,2-trifluoro-ethoxy)-thiophene), and a new pyrazine derivative (2,3-dibenzyl-5,7-di(thien-2-yl)thieno[3,4-b]pyrazine) are also disclosed, since these materials are all able to selectively change to a green color state, and can be polymerized to achieve a green EC polymer.

Green electrochromic (EC) material and device

Large contrast ratio and rapid switching laminated electrochromic (EC) polymer device includes transparent electrode, cathodic EC polymer, gel electrolyte, and counter-electrode. Preferably the cathodic EC polymer is a poly(3,4-propylenedioxythiophene) derivative, PProDOT-Me. Counter-electrode is a conductive coating deposited on transparent substrate, with preferred coatings including gold and highly conductive carbon. Lithography and sputtering can be employed to pattern a gold layer, while screen printing can be employed to similarly pattern graphite. Empirical studies of preferred device indicate a color change of high contrast ratio of transmittance (&#x3e;50% T) is rapidly (0.5&#x2013;1 s) obtained upon applied 2.5V, repeatable to at least 10,000 times, as estimated by electrochemistry. Dual layer EC devices including PProDOT-Meare also disclosed, as are methods for synthesizing preferred EC polymers. Preferred synthesis method for obtaining PProDOT-Meinvolves refluxing reagents in toluene in the presence of catalyst, while continually removing methanol byproduct from refluxing solution.

Electrochromic organic polymer synthesis and devices utilizing electrochromic organic polymers

Large contrast ratio and rapid switching laminated electrochromic (EC) polymer device includes transparent electrode, cathodic EC polymer, gel electrolyte, and counter-electrode. Preferably the cathodic EC polymer is a poly(3,4-propylenedioxythiophene) derivative, PProDOT-Me. Counter-electrode is a conductive coating deposited on transparent substrate, with preferred coatings including gold and highly conductive carbon. Lithography and sputtering can be employed to pattern a gold layer, while screen printing can be employed to similarly pattern graphite. Empirical studies of preferred device indicate a color change of high contrast ratio of transmittance (&#x3e;50% T) is rapidly (0.5&#x2013;1s) obtained upon applied 2.5V, repeatable to at least 10,000 times, as estimated by electrochemistry. Dual layer EC devices including PProDOT-Meare also disclosed, as are methods for synthesizing preferred EC polymers. Preferred synthesis method for obtaining PProDOT-Meinvolves refluxing reagents in toluene in the presence of catalyst, while continually removing methanol byproduct from refluxing solution.

Large contrast ratio and rapid switching laminated electrochromic (EC) polymer device includes transparent electrode, cathodic EC polymer, gel electrolyte, and counter-electrode. Preferably the cathodic EC polymer is a poly(3,4-propylenedioxythiophene) derivative, PProDOT-Me . Counter-electrode is a conductive coating deposited on transparent substrate, with preferred coatings including gold and highly conductive carbon. Lithography and sputtering can be employed to pattern a gold layer, while screen printing can be employed to similarly pattern graphite. Empirical studies of preferred device indicate a color change of high contrast ratio of transmittance (>50% T) is rapidly (0.5-1s) obtained upon applied 2.5V, repeatable to at least 10,000 times, as estimated by electrochemistry. Dual layer EC devices including PProDOT-Me are also disclosed, as are methods for synthesizing preferred EC polymers. Preferred synthesis method for obtaining PProDOT-Me involves refluxing reagents in toluene in the presence of catalyst, while continually removing methanol byproduct from refluxing solution.

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Seattle, WA, United States of America

Chunye Xu