US20090122389A1 - Electro-optic assemblies, and adhesives and binders for use therein - Google Patents

Electro-optic assemblies, and adhesives and binders for use therein Download PDF

Info

Publication number
US20090122389A1
US20090122389A1 US12/264,696 US26469608A US2009122389A1 US 20090122389 A1 US20090122389 A1 US 20090122389A1 US 26469608 A US26469608 A US 26469608A US 2009122389 A1 US2009122389 A1 US 2009122389A1
Authority
US
United States
Prior art keywords
electro
optic
material
fluid
assembly according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US12/264,696
Inventor
Thomas H. Whitesides
Lan Cao
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
E Ink Corp
Original Assignee
E Ink Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US98787607P priority Critical
Application filed by E Ink Corp filed Critical E Ink Corp
Priority to US12/264,696 priority patent/US20090122389A1/en
Assigned to E INK CORPORATION reassignment E INK CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: WHITESIDES, THOMAS H., CAO, LAN
Publication of US20090122389A1 publication Critical patent/US20090122389A1/en
Application status is Abandoned legal-status Critical

Links

Images

Classifications

    • GPHYSICS
    • G02OPTICS
    • G02FDEVICES OR ARRANGEMENTS, THE OPTICAL OPERATION OF WHICH IS MODIFIED BY CHANGING THE OPTICAL PROPERTIES OF THE MEDIUM OF THE DEVICES OR ARRANGEMENTS FOR THE CONTROL OF THE INTENSITY, COLOUR, PHASE, POLARISATION OR DIRECTION OF LIGHT, e.g. SWITCHING, GATING, MODULATING OR DEMODULATING; TECHNIQUES OR PROCEDURES FOR THE OPERATION THEREOF; FREQUENCY-CHANGING; NON-LINEAR OPTICS; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices 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
    • G02F1/01Devices 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 
    • G02F1/165Devices 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 translational movement of particles in a fluid under the influence of an applied field
    • G02F1/166Devices 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 translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect
    • G02F1/167Devices 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 translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect by electrophoresis
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/0804Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0809Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
    • C08G18/0814Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/0804Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4825Polyethers containing two hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666Compounds of group C08G18/48 or C08G18/52
    • C08G18/6692Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7628Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
    • C08G18/765Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/44Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • C09D5/4419Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
    • C09D5/4465Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/30Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38Pressure-sensitive adhesives [PSA]
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02Electrically-conducting adhesives
    • GPHYSICS
    • G02OPTICS
    • G02FDEVICES OR ARRANGEMENTS, THE OPTICAL OPERATION OF WHICH IS MODIFIED BY CHANGING THE OPTICAL PROPERTIES OF THE MEDIUM OF THE DEVICES OR ARRANGEMENTS FOR THE CONTROL OF THE INTENSITY, COLOUR, PHASE, POLARISATION OR DIRECTION OF LIGHT, e.g. SWITCHING, GATING, MODULATING OR DEMODULATING; TECHNIQUES OR PROCEDURES FOR THE OPERATION THEREOF; FREQUENCY-CHANGING; NON-LINEAR OPTICS; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices 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
    • G02F1/01Devices 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 
    • G02F1/15Devices 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
    • G02F1/153Constructional details
    • G02F1/1533Constructional details structural features not otherwise provided for
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2170/00Compositions for adhesives
    • C08G2170/80Compositions for aqueous adhesives
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUSE OF INORGANIC OR NON-MACROMOLECULAR ORGANIC SUBSTANCES AS COMPOUNDING INGREDIENTS
    • C08K5/00Use of organic ingredients
    • C08K5/0008Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0075Antistatics
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUSE OF INORGANIC OR NON-MACROMOLECULAR ORGANIC SUBSTANCES AS COMPOUNDING INGREDIENTS
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/17Amines; Quaternary ammonium compounds
    • C08K5/19Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUSE OF INORGANIC OR NON-MACROMOLECULAR ORGANIC SUBSTANCES AS COMPOUNDING INGREDIENTS
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2205/00Other features
    • C09J2205/10Other features of adhesive tapes; Production process thereof
    • C09J2205/102Other features of adhesive tapes; Production process thereof additives as essential feature of the adhesive layer, the additive itself being indicated with the corresponding code of C08K
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2475/00Presence of polyurethane
    • GPHYSICS
    • G02OPTICS
    • G02FDEVICES OR ARRANGEMENTS, THE OPTICAL OPERATION OF WHICH IS MODIFIED BY CHANGING THE OPTICAL PROPERTIES OF THE MEDIUM OF THE DEVICES OR ARRANGEMENTS FOR THE CONTROL OF THE INTENSITY, COLOUR, PHASE, POLARISATION OR DIRECTION OF LIGHT, e.g. SWITCHING, GATING, MODULATING OR DEMODULATING; TECHNIQUES OR PROCEDURES FOR THE OPERATION THEREOF; FREQUENCY-CHANGING; NON-LINEAR OPTICS; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices 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
    • G02F1/01Devices 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 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating, or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1334Constructional arrangements; Manufacturing methods based on polymer dispersed liquid crystals, e.g. microencapsulated liquid crystals
    • GPHYSICS
    • G02OPTICS
    • G02FDEVICES OR ARRANGEMENTS, THE OPTICAL OPERATION OF WHICH IS MODIFIED BY CHANGING THE OPTICAL PROPERTIES OF THE MEDIUM OF THE DEVICES OR ARRANGEMENTS FOR THE CONTROL OF THE INTENSITY, COLOUR, PHASE, POLARISATION OR DIRECTION OF LIGHT, e.g. SWITCHING, GATING, MODULATING OR DEMODULATING; TECHNIQUES OR PROCEDURES FOR THE OPERATION THEREOF; FREQUENCY-CHANGING; NON-LINEAR OPTICS; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices 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
    • G02F1/01Devices 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 
    • G02F1/165Devices 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 translational movement of particles in a fluid under the influence of an applied field
    • G02F1/1675Constructional details
    • G02F1/1679Gaskets; Spacers; Sealing of cells; Filling or closing of cells
    • G02F1/1681Gaskets; Spacers; Sealing of cells; Filling or closing of cells having two or more microcells partitioned by walls, e.g. of microcup type
    • GPHYSICS
    • G02OPTICS
    • G02FDEVICES OR ARRANGEMENTS, THE OPTICAL OPERATION OF WHICH IS MODIFIED BY CHANGING THE OPTICAL PROPERTIES OF THE MEDIUM OF THE DEVICES OR ARRANGEMENTS FOR THE CONTROL OF THE INTENSITY, COLOUR, PHASE, POLARISATION OR DIRECTION OF LIGHT, e.g. SWITCHING, GATING, MODULATING OR DEMODULATING; TECHNIQUES OR PROCEDURES FOR THE OPERATION THEREOF; FREQUENCY-CHANGING; NON-LINEAR OPTICS; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2202/00Materials and properties
    • G02F2202/28Adhesive materials or arrangements

Abstract

An electro-optic assembly comprises an adhesive layer and a layer of electro-optic material. The adhesive layer comprises a polymeric adhesive material and an ionic material having either its cation or its anion fixed to the polymeric adhesive material. The ionic material reduces the volume resistivity of the polymeric adhesive material and is not removed upon heating to 50° C. In a similar electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprises a polymeric adhesive material which has been subjected to dialysis or diafiltration to remove organic species having a molecular weight less than about 3,500, so that the adhesive material has a content of N-methylpyrrolidone not exceeding 500 ppm based upon the total weight of the adhesive layer and layer of electro-optic material.

Description

    REFERENCE TO RELATED APPLICATIONS
  • This application claims benefit of copending Application Ser. No. 60/987,876, filed Nov. 14, 2007.
  • This application is also related to:
      • (a) U.S. Pat. No. 7,012,735;
      • (b) U.S. Pat. No. 7,173,752; and
      • (c) copending Application Ser. No. 61/052,427, filed May 12, 2008.
  • The entire contents of these patents and copending applications, and of all other U.S. patents and published and copending applications mentioned below, are herein incorporated by reference.
  • BACKGROUND OF INVENTION
  • This invention relates to electro-optic assemblies useful in the production of electro-optic displays, and to adhesives and binders for use in such assemblies. More specifically, this invention provides adhesive and binder compositions having controlled volume resistivity, and electro-optic assemblies and displays incorporating such adhesives. The adhesives disclosed herein may be useful in applications other than electro-optic displays.
  • Electro-optic displays comprise a layer of electro-optic material, a term which is used herein in its conventional meaning in the art to refer to a material having first and second display states differing in at least one optical property, the material being changed from its first to its second display state by application of an electric field to the material. The optical property is typically color perceptible to the human eye, but may be another optical property, such as optical transmission, reflectance, luminescence or, in the case of displays intended for machine reading, pseudo-color in the sense of a change in reflectance of electromagnetic wavelengths outside the visible range.
  • Some electro-optic materials are solid in the sense that the materials have solid external surfaces, although the materials may, and often do, have internal liquid- or gas-filled spaces. Such displays using solid electro-optic materials may hereinafter for convenience be referred to as “solid electro-optic displays”. Thus, the term “solid electro-optic displays” includes rotating bichromal member displays, encapsulated electrophoretic displays, microcell electrophoretic displays and encapsulated liquid crystal displays.
  • The terms “bistable” and “bistability” are used herein in their conventional meaning in the art to refer to displays comprising display elements having first and second display states differing in at least one optical property, and such that after any given element has been driven, by means of an addressing pulse of finite duration, to assume either its first or second display state, after the addressing pulse has terminated, that state will persist for at least several times, for example at least four times, the minimum duration of the addressing pulse required to change the state of the display element. It is shown in U.S. Pat. No. 7,170,670 that some particle-based electrophoretic displays capable of gray scale are stable not only in their extreme black and white states but also in their intermediate gray states, and the same is true of some other types of electro-optic displays. This type of display is properly called “multi-stable” rather than bistable, although for convenience the term “bistable” may be used herein to cover both bistable and multi-stable displays.
  • Several types of electro-optic displays are known. One type of electro-optic display is a rotating bichromal member type as described, for example, in U.S. Pat. Nos. 5,808,783; 5,777,782; 5,760,761; 6,054,071 6,055,091; 6,097,531; 6,128,124; 6,137,467; and 6,147,791 (although this type of display is often referred to as a “rotating bichromal ball” display, the term “rotating bichromal member” is preferred as more accurate since in some of the patents mentioned above the rotating members are not spherical). Such a display uses a large number of small bodies (typically spherical or cylindrical) which have two or more sections with differing optical characteristics, and an internal dipole. These bodies are suspended within liquid-filled vacuoles within a matrix, the vacuoles being filled with liquid so that the bodies are free to rotate. The appearance of the display is changed by applying an electric field thereto, thus rotating the bodies to various positions and varying which of the sections of the bodies is seen through a viewing surface. This type of electro-optic medium is typically bistable.
  • Another type of electro-optic display uses an electrochromic medium, for example an electrochromic medium in the form of a nanochromic film comprising an electrode formed at least in part from a semi-conducting metal oxide and a plurality of dye molecules capable of reversible color change attached to the electrode; see, for example O'Regan, B., et al., Nature 1991, 353, 737; and Wood, D., Information Display, 18(3), 24 (March 2002). See also Bach, U., et al., Adv. Mater., 2002, 14(11), 845. Nanochromic films of this type are also described, for example, in U.S. Pat. Nos. 6,301,038; 6,870.657; and 6,950,220. This type of medium is also typically bistable.
  • Another type of electro-optic display is an electro-wetting display developed by Philips and described in Hayes, R. A., et al., “Video-Speed Electronic Paper Based on Electrowetting”, Nature, 425, 383-385 (2003). It is shown in copending application Ser. No. 10/711,802, filed Oct. 6, 2004 (Publication No. 2005/0151709), that such electro-wetting displays can be made bistable.
  • One type of electro-optic display, which has been the subject of intense research and development for a number of years, is the particle-based electrophoretic display, in which a plurality of charged particles move through a fluid under the influence of an electric field. Electrophoretic displays can have attributes of good brightness and contrast, wide viewing angles, state bistability, and low power consumption when compared with liquid crystal displays. Nevertheless, problems with the long-term image quality of these displays have prevented their widespread usage. For example, particles that make up electrophoretic displays tend to settle, resulting in inadequate service-life for these displays.
  • As noted above, electrophoretic media require the presence of a fluid. In most prior art electrophoretic media, this fluid is a liquid, but electrophoretic media can be produced using gaseous fluids; see, for example, Kitamura, T., et al., “Electrical toner movement for electronic paper-like display”, IDW Japan, 2001, Paper HCS1-1, and Yamaguchi, Y, et al., “Toner display using insulative particles charged triboelectrically”, IDW Japan, 2001, Paper AMD4-4). See also U.S. Patent Publication Nos. 2005/0259068, 2006/0087479, 2006/0087489, 2006/0087718, 2006/0209008, 2006/0214906, 2006/0231401, 2006/0238488, 2006/0263927 and U.S. Pat. Nos. 7,321,459 and 7,236,291. Such gas-based electrophoretic media appear to be susceptible to the same types of problems due to particle settling as liquid-based electrophoretic media, when the media are used in an orientation which permits such settling, for example in a sign where the medium is disposed in a vertical plane. Indeed, particle settling appears to be a more serious problem in gas-based electrophoretic media than in liquid-based ones, since the lower viscosity of gaseous suspending fluids as compared with liquid ones allows more rapid settling of the electrophoretic particles.
  • Numerous patents and applications assigned to or in the names of the Massachusetts Institute of Technology (MIT) and E Ink Corporation describe various technologies used in encapsulated electrophoretic and other electro-optic media. Such encapsulated media comprise numerous small capsules, each of which itself comprises an internal phase containing electrophoretically-mobile particles in a fluid medium, and a capsule wall surrounding the internal phase. Typically, the capsules are themselves held within a polymeric binder to form a coherent layer positioned between two electrodes. The technologies described in the these patents and applications include:
      • (a) Electrophoretic particles, fluids and fluid additives; see for example U.S. Pat. No. 7,002,728 and U.S. Patent Application Publication No. 2007/0146310;
      • (b) Capsules, binders and encapsulation processes; see for example U.S. Pat. Nos. 5,930,026; 6,067,185; 6,130,774; 6,172,798; 6,249,271; 6,327,072; 6,392,785; 6,392,786; 6,459,418; 6,839,158; 6,866,760; 6,922,276; 6,958,848; 6,987,603; 7,061,663; 7,071,913; 7,079,305; 7,109,968; 7,110,164; 7,202,991; 7,242,513; 7,304,634; 7,339,715; and 7,391,555; and U.S. Patent Applications Publication Nos. 2004/0112750; 2004/0155857; 2005/0156340; 2006/0007527; 2007/0057908; 2007/0091417; 2007/0223079; 2008/0023332; and 2008/0130092;
      • (c) Films and sub-assemblies containing electro-optic materials; see for example U.S. Pat. No. 6,982,178 and U.S. Patent Application Publication No. 2007/0109219;
      • (d) Backplanes, adhesive layers and other auxiliary layers and methods used in displays; see for example U.S. Pat. Nos. D485,294; 6,124,851; 6,130,773; 6,177,921; 6,232,950; 6,252,564; 6,312,304; 6,312,971; 6,376,828; 6,392,786; 6,413,790; 6,422,687; 6,445,374; 6,480,182; 6,498,114; 6,506,438; 6,518,949; 6,521,489; 6,535,197; 6,545,291; 6,639,578; 6,657,772; 6,664,944; 6,680,725; 6,683,333; 6,724,519; 6,750,473; 6,816,147; 6,819,471; 6,825,068; 6,831,769; 6,842,167; 6,842,279; 6,842,657; 6,865,010; 6,967,640; 6,980,196; 7,012,735; 7,030,412; 7,075,703; 7,106,296; 7,110,163; 7,116,318; 7,148,128; 7,167,155; 7,173,752; 7,176,880; 7,190,008; 7,206,119; 7,223,672; 7,230,751; 7,256,766; 7,259,744; 7,280,094; 7,327,511; 7,349,148; 7,352,353; 7,365,394; 7,365,733; 7,382,363; and 7,388,572; and U.S. Patent Applications Publication Nos. 2002/0060321; 2004/0105036; 2004/0180476; 2005/0122306; 2005/0122563; 2006/0176267; 2006/0223282; 2006/0291034; 2007/0035532; 2007/0035808; 2007/0052757; 2007/0069247; 2007/0085818; 2007/0097489; 2007/0109219; 2007/0152956; 2007/0211002; 2007/0211331; 2007/0247697; 2007/0286975; 2008/0030832; 2008/0057252; and 2008/0074730; International Application Publication No. WO 00/38000; and European Patents Nos. 1,099,207 B1 and 1,145,072 B1;
      • (e) Color formation and color adjustment; see for example U.S. Pat. No. 7,075,502 and U.S. Patent Application Publication No. 2007/0109219;
      • (f) Methods for driving displays; see for example U.S. Pat. No. 7,012,600 and U.S. Patent Application Publication No. 2006/0262060;
      • (g) Applications of displays; see for example U.S. Pat. No. 7,312,784 and U.S. Patent Application Publication No. 2006/0279527; and
      • (h) Non-electrophoretic displays, as described in U.S. Pat. Nos. 6,241,921; and 6,950,220; and U.S. Patent Application Publication No. 2005/0151709.
  • Many of the aforementioned patents and applications recognize that the walls surrounding the discrete microcapsules in an encapsulated electrophoretic medium could be replaced by a continuous phase, thus producing a so-called polymer-dispersed electrophoretic display, in which the electrophoretic medium comprises a plurality of discrete droplets of an electrophoretic fluid and a continuous phase of a polymeric material, and that the discrete droplets of electrophoretic fluid within such a polymer-dispersed electrophoretic display may be regarded as capsules or microcapsules even though no discrete capsule membrane is associated with each individual droplet; see for example, the aforementioned U.S. Pat. No. 6,866,760. Accordingly, for purposes of the present application, such polymer-dispersed electrophoretic media are regarded as sub-species of encapsulated electrophoretic media.
  • A related type of electrophoretic display is a so-called “microcell electrophoretic display”. In a microcell electrophoretic display, the charged particles and the fluid are not encapsulated within microcapsules but instead are retained within a plurality of cavities formed within a carrier medium, typically a polymeric film. See, for example, U.S. Pat. Nos. 6,672,921 and 6,788,449, both assigned to Sipix Imaging, Inc.
  • Although electrophoretic media are often opaque (since, for example, in many electrophoretic media, the particles substantially block transmission of visible light through the display) and operate in a reflective mode, many electrophoretic displays can be made to operate in a so-called “shutter mode” in which one display state is substantially opaque and one is light-transmissive. See, for example, the aforementioned U.S. Pat. Nos. 6,130,774 and 6,172,798, and U.S. Pat. Nos. 5,872,552; 6,144,361; 6,271,823; 6,225,971; and 6,184,856. Dielectrophoretic displays, which are similar to electrophoretic displays but rely upon variations in electric field strength, can operate in a similar mode; see U.S. Pat. No. 4,418,346. Other types of electro-optic displays may also be capable of operating in shutter mode.
  • An encapsulated electrophoretic display typically does not suffer from the clustering and settling failure mode of traditional electrophoretic devices and provides further advantages, such as the ability to print or coat the display on a wide variety of flexible and rigid substrates. (Use of the word “printing” is intended to include all forms of printing and coating, including, but without limitation: pre-metered coatings such as patch die coating, slot or extrusion coating, slide or cascade coating, curtain coating; roll coating such as knife over roll coating, forward and reverse roll coating; gravure coating; dip coating; spray coating; meniscus coating; spin coating; brush coating; air knife coating; silk screen printing processes; electrostatic printing processes; thermal printing processes; ink jet printing processes; electrophoretic deposition (See U.S. Pat. No. 7,339,715); and other similar techniques.) Thus, the resulting display can be flexible. Further, because the display medium can be printed (using a variety of methods), the display itself can be made inexpensively.
  • Other types of electro-optic media, for example, polymer-dispersed liquid crystal, may also be used in the displays of the present invention.
  • An electro-optic display normally comprises a layer of electro-optic material and at least two other layers disposed on opposed sides of the electro-optic material, one of these two layers being an electrode layer. In most such displays both the layers are electrode layers, and one or both of the electrode layers are patterned to define the pixels of the display. For example, one electrode layer may be patterned into elongate row electrodes and the other into elongate column electrodes running at right angles to the row electrodes, the pixels being defined by the intersections of the row and column electrodes. Alternatively, and more commonly, one electrode layer has the form of a single continuous electrode and the other electrode layer is patterned into a matrix of pixel electrodes, each of which defines one pixel of the display. In another type of electro-optic display, which is intended for use with a stylus, print head or similar movable electrode separate from the display, only one of the layers adjacent the electro-optic layer comprises an electrode, the layer on the opposed side of the electro-optic layer typically being a protective layer intended to prevent the movable electrode damaging the electro-optic layer.
  • The manufacture of a three-layer electro-optic display normally involves at least one lamination operation. For example, in several of the aforementioned MIT and E Ink patents and applications, there is described a process for manufacturing an encapsulated electrophoretic display in which an encapsulated electrophoretic medium comprising capsules in a binder is coated on to a flexible substrate comprising indium-tin-oxide (ITO) or a similar conductive coating (which acts as one electrode of the final display) on a plastic film, the capsules/binder coating being dried to form a coherent layer of the electrophoretic medium firmly adhered to the substrate. Separately, a backplane, containing an array of pixel electrodes and an appropriate arrangement of conductors to connect the pixel electrodes to drive circuitry, is prepared. To form the final display, the substrate having the capsule/binder layer thereon is laminated to the backplane using a lamination adhesive. (A very similar process can be used to prepare an electrophoretic display usable with a stylus or similar movable electrode by replacing the backplane with a simple protective layer, such as a plastic film, over which the stylus or other movable electrode can slide.) In one preferred form of such a process, the backplane is itself flexible and is prepared by printing the pixel electrodes and conductors on a plastic film or other flexible substrate. The obvious lamination technique for mass production of displays by this process is roll lamination using a lamination adhesive. Similar manufacturing techniques can be used with other types of electro-optic displays. For example, a microcell electrophoretic medium or a rotating bichromal member medium may be laminated to a backplane in substantially the same manner as an encapsulated electrophoretic medium.
  • As discussed in the aforementioned U.S. Pat. No. 6,982,178, (see column 3, lines 63 to column 5, line 46) many of the components used in solid electro-optic displays, and the methods used to manufacture such displays, are derived from technology used in liquid crystal displays (LCD's), which are of course also electro-optic displays, though using a liquid rather than a solid medium. For example, solid electro-optic displays may make use of an active matrix backplane comprising an array of transistors or diodes and a corresponding array of pixel electrodes, and a “continuous” front electrode (in the sense of an electrode which extends over multiple pixels and typically the whole display) on a transparent substrate, these components being essentially the same as in LCD's. However, the methods used for assembling LCD's cannot be used with solid electro-optic displays. LCD's are normally assembled by forming the backplane and front electrode on separate glass substrates, then adhesively securing these components together leaving a small aperture between them, placing the resultant assembly under vacuum, and immersing the assembly in a bath of the liquid crystal, so that the liquid crystal flows through the aperture between the backplane and the front electrode. Finally, with the liquid crystal in place, the aperture is sealed to provide the final display.
  • This LCD assembly process cannot readily be transferred to solid electro-optic displays. Because the electro-optic material is solid, it must be present between the backplane and the front electrode before these two integers are secured to each other. Furthermore, in contrast to a liquid crystal material, which is simply placed between the front electrode and the backplane without being attached to either, a solid electro-optic medium normally needs to be secured to both; in most cases the solid electro-optic medium is formed on the front electrode, since this is generally easier than forming the medium on the circuitry-containing backplane, and the front electrode/electro-optic medium combination is then laminated to the backplane, typically by covering the entire surface of the electro-optic medium with an adhesive and laminating under heat, pressure and possibly vacuum. Accordingly, most prior art methods for final lamination of solid electrophoretic displays are essentially batch methods in which (typically) the electro-optic medium, a lamination adhesive and a backplane are brought together immediately prior to final assembly, and it is desirable to provide methods better adapted for mass production.
  • Electro-optic displays are often costly; for example, the cost of the color LCD found in a portable computer is typically a substantial fraction of the entire cost of the computer. As the use of electro-optic displays spreads to devices, such as cellular telephones and personal digital assistants (PDA's), much less costly than portable computers, there is great pressure to reduce the costs of such displays. The ability to form layers of some solid electro-optic media by printing techniques on flexible substrates, as discussed above, opens up the possibility of reducing the cost of electro-optic components of displays by using mass production techniques such as roll-to-roll coating using commercial equipment used for the production of coated papers, polymeric films and similar media.
  • U.S. Pat. No. 6,982,178 describes a method of assembling a solid electro-optic display (including an encapsulated electrophoretic display) which is well adapted for mass production. Essentially, this patent describes a so-called “front plane laminate” (“FPL”) which comprises, in order, a light-transmissive electrically-conductive layer; a layer of a solid electro-optic medium in electrical contact with the electrically-conductive layer; an adhesive layer; and a release sheet. Typically, the light-transmissive electrically-conductive layer will be carried on a light-transmissive substrate, which is preferably flexible, in the sense that the substrate can be manually wrapped around a drum (say) 10 inches (254 mm) in diameter without permanent deformation. The term “light-transmissive” is used in this patent and herein to mean that the layer thus designated transmits sufficient light to enable an observer, looking through that layer, to observe the change in display states of the electro-optic medium, which will normally be viewed through the electrically-conductive layer and adjacent substrate (if present); in cases where the electro-optic medium displays a change in reflectivity at non-visible wavelengths, the term “light-transmissive” should of course be interpreted to refer to transmission of the relevant non-visible wavelengths. The substrate will typically be a polymeric film, and will normally have a thickness in the range of about 1 to about 25 mil (25 to 634 μm), preferably about 2 to about 10 mil (51 to 254 μm). The electrically-conductive layer is conveniently a thin metal or metal oxide layer of, for example, aluminum or ITO, or may be a conductive polymer. Poly(ethylene terephthalate) (PET) films coated with aluminum or ITO are available commercially, for example as “aluminized Mylar” (“Mylar” is a Registered Trade Mark) from E.I. du Pont de Nemours & Company, Wilmington Del., and such commercial materials may be used with good results in the front plane laminate.
  • The aforementioned U.S. Pat. No. 6,982,178 also describes a method for testing the electro-optic medium in a front plane laminate prior to incorporation of the front plane laminate into a display. In this testing method, the release sheet is provided with an electrically conductive layer, and a voltage sufficient to change the optical state of the electro-optic medium is applied between this electrically conductive layer and the electrically conductive layer on the opposed side of the electro-optic medium. Observation of the electro-optic medium will then reveal any faults in the medium, thus avoiding laminating faulty electro-optic medium into a display, with the resultant cost of scrapping the entire display, not merely the faulty front plane laminate.
  • The aforementioned U.S. Pat. No. 6,982,178 also describes a second method for testing the electro-optic medium in a front plane laminate by placing an electrostatic charge on the release sheet, thus forming an image on the electro-optic medium. This image is then observed in the same way as before to detect any faults in the electro-optic medium.
  • Assembly of an electro-optic display using such a front plane laminate may be effected by removing the release sheet from the front plane laminate and contacting the adhesive layer with the backplane under conditions effective to cause the adhesive layer to adhere to the backplane, thereby securing the adhesive layer, layer of electro-optic medium and electrically-conductive layer to the backplane. This process is well-adapted to mass production since the front plane laminate may be mass produced, typically using roll-to-roll coating techniques, and then cut into pieces of any size needed for use with specific backplanes.
  • The aforementioned 2004/0155857 describes a so-called “double release sheet” which is essentially a simplified version of the front plane laminate of the aforementioned U.S. Pat. No. 6,982,178. One form of the double release sheet comprises a layer of a solid electro-optic medium sandwiched between two adhesive layers, one or both of the adhesive layers being covered by a release sheet. Another form of the double release sheet comprises a layer of a solid electro-optic medium sandwiched between two release sheets. Both forms of the double release film are intended for use in a process generally similar to the process for assembling an electro-optic display from a front plane laminate already described, but involving two separate laminations; typically, in a first lamination the double release sheet is laminated to a front electrode to form a front sub-assembly, and then in a second lamination the front sub-assembly is laminated to a backplane to form the final display, although the order of these two laminations could be reversed if desired.
  • The aforementioned 2007/0109219 describes a so-called “inverted front plane laminate”, which is a variant of the front plane laminate described in the aforementioned U.S. Pat. No. 6,982,178. This inverted front plane laminate comprises, in order, at least one of a light-transmissive protective layer and a light-transmissive electrically-conductive layer; an adhesive layer; a layer of a solid electro-optic medium; and a release sheet. This inverted front plane laminate is used to form an electro-optic display having a layer of lamination adhesive between the electro-optic layer and the front electrode or front substrate; a second, typically thin layer of adhesive may or may not be present between the electro-optic layer and a backplane. Such electro-optic displays can combine good resolution with good low temperature performance. As discussed in the aforementioned U.S. Pat. Nos. 7,012,735 and 7,173,752, the selection of a lamination adhesive for use in an electro-optic display (or in a front plane laminate, inverted front plane laminate, double release film or other sub-assembly used to produce such an electro-optic display) presents certain peculiar problems. Since the lamination adhesive is normally located between the electrodes, which apply the electric field needed to change the electrical state of the electro-optic medium, the electrical properties of the adhesive are usually crucial. The lamination adhesive also needs to fulfill several mechanical and rheological criteria, including strength of adhesive, flexibility, ability to withstand and flow at lamination temperatures, etc. The number of commercially available adhesives which can fulfill all the relevant electrical and mechanical criteria is small, and in practice the most suitable lamination adhesives are certain polyurethanes, such as those described in U.S. Patent Application Publication No. 2005/0107564. These polyurethanes are based on the polymerization of tetramethylxylene diisocyanate (TMXDI—systematic name 1,3-bis(1-isocyanato-1-methylethyl)-benzene)) with polypropylene glycol and 2,2-bis(hydroxymethyl)propionic acid, chain extended with hexamethylene diamine. After the polyurethane is prepared, it is dispersed as an aqueous latex-like suspension by neutralization with triethylamine and dilution with water. However, in practice it is not possible to vary the conductivity of the polyurethane by controlling the proportions of the materials used in its manufacture.
  • As a result, the polyurethane adhesive is not sufficiently conductive for use in many electro-optic displays and electro-optic assemblies, and it known to increase its conductivity by doping it with salts or other materials, as described in the aforementioned U.S. Pat. Nos. 7,012,735 and 7,173,752. A preferred dopant for this purpose is tetrabutylammonium hexafluorophosphate (hereinafter “TBAHFP”). Unfortunately, it has been found that adhesives formulated in this manner can damage active matrix backplanes comprising transistors made from certain organic semiconductors. The present invention provides alternative forms of lamination adhesive which can reduce or eliminate the problems caused by prior art adhesives when used in displays containing organic semiconductors. The present invention also extends to modification of the binder used in electro-optic displays to reduce or eliminate problems caused by prior art binders in displays containing organic semiconductors.
  • SUMMARY OF INVENTION
  • This invention has two main aspects. The first aspect relates to incorporation of an ionic material into an adhesive layer in a manner which does not permit the material to diffuse out of the adhesive layer. The second aspect relates to pre-treatment of adhesive material or binder to remove certain diffusible species which may damage organic semiconductors.
  • Accordingly, in one aspect this invention provides an electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprising a polymeric adhesive material and an ionic material, the ionic material having one of its cation and anion fixed to the polymeric adhesive material and the other of its cation and anion free to migrate through the polymeric adhesive material, the ionic material reducing the volume resistivity of the polymeric adhesive material and not being removed by heating the polymeric adhesive material to about 50° C.
  • Hereinafter for convenience the cation or anion of the ionic material which is fixed to the polymeric adhesive material will be called the “fixed ion” and the cation or anion free to migrate through the polymeric adhesive material will be called the “mobile ion”. Typically, the fixed ion will be chemically bonded to the polymeric adhesive, and various techniques for providing such ions bonded to polyurethane adhesives are discussed below. However, such chemical bonding is not absolutely necessary, provided that the fixed ion cannot migrate through the polymeric adhesive; for example, the fixed ion could form part of a polymer different from the polymeric adhesive but chain entangled therewith.
  • In one form of the electro-optic assembly, the ionic material comprises a quaternary ammonium or phosphonium cation and a carboxylate anion fixed to the polymeric adhesive material. The polymeric adhesive material may comprise a polyurethane. Alternatively, the ionic material may comprise a quaternary ammonium or phosphonium cation fixed to the polymeric adhesive material and a hexafluorophosphate, tetrabutylborate or tetraphenylborate anion. In another form of the electro-optic assembly, the ionic material comprises repeating units derived from a basic monomer and a mobile anion selected from the group comprising sulfonates, sulfates, hexafluorophosphates, tetrafluoroborates, bis(methanesulfonyl)imidate, phosphates and phosphonates. The basic monomer may comprise, for example, any one or more of vinylpyridine, β-dimethylaminoethyl acrylate, N-methyl or benzyl(vinylpyridine), N-alkyl or alkaryl-N′-vinylimidazole, and β-(trimethylammonioethyl)acrylate or methacrylate.
  • In such an electro-optic assembly, the electro-optic material may comprise a rotating bichromal member or electrochromic material. Alternatively, the electro-optic material may comprise an electrophoretic material comprising a plurality of electrically charged particles disposed in a fluid and capable of moving through the fluid under the influence of an electric field. The electrically charged particles and the fluid may be confined within a plurality of capsules or microcells. Alternatively, the electrically charged particles and the fluid may be present as a plurality of discrete droplets surrounded by a continuous phase comprising a polymeric material. The fluid may be liquid or gaseous.
  • The present invention extends to an electro-optic display, front plane laminate, inverted front plane laminate or double release film comprising an electro-optic assembly of the present invention.
  • The present invention also provides an electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprising a polymeric adhesive material which has been subjected to dialysis or diafiltration to remove organic species having a molecular weight less than about 3,500.
  • The present invention also provides an electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprising a polymeric adhesive material having a content of N-methylpyrrolidone not exceeding about 500 ppm based upon the total weight of the adhesive layer and layer of electro-optic material.
  • In such an electro-optic assembly, the polymeric adhesive material may comprise a polyurethane. The content of N-methylpyrrolidone preferably does not exceed about 200 ppm and desirably 100 ppm, based upon the total weight of the adhesive layer and layer of electro-optic material.
  • In such an electro-optic assembly, the electro-optic material may comprise a rotating bichromal member or electrochromic material. Alternatively, the electro-optic material may comprise an electrophoretic material comprising a plurality of electrically charged particles disposed in a fluid and capable of moving through the fluid under the influence of an electric field. The electrically charged particles and the fluid may be confined within a plurality of capsules or microcells. Alternatively, the electrically charged particles and the fluid may be present as a plurality of discrete droplets surrounded by a continuous phase comprising a polymeric material. The fluid may be liquid or gaseous.
  • The present invention extends to an electro-optic display, front plane laminate, inverted front plane laminate or double release film comprising an electro-optic assembly of the present invention.
  • The present invention also provides an electrophoretic medium comprising a continuous phase and a discontinuous phase, the discontinuous phase comprising a plurality of droplets, each of which comprises a suspending fluid and at least one particle disposed within the suspending fluid and capable of moving through the fluid upon application of an electric field to the electrophoretic medium, the continuous phase surrounding and encapsulating the discontinuous phase and comprising a polymeric binder which has been subjected to dialysis or diafiltration to remove organic species having a molecular weight less than about 3,500. The electrophoretic medium may be either of the encapsulated or polymer-dispersed type, i.e., there may or may not be a capsule wall between each droplet and the binder.
  • The present invention also provides an electrophoretic medium comprising a continuous phase and a discontinuous phase, the discontinuous phase comprising a plurality of droplets, each of which comprises a suspending fluid and at least one particle disposed within the suspending fluid and capable of moving through the fluid upon application of an electric field to the electrophoretic medium, the continuous phase surrounding and encapsulating the discontinuous phase and comprising a polymeric binder having a content of N-methylpyrrolidone not exceeding about 1000 ppm based upon the weight of the electrophoretic medium.
  • The present invention extends to an electro-optic display, front plane laminate, inverted front plane laminate or double release film comprising an electro-optic assembly or electrophoretic medium of the present invention.
  • The displays of the present invention may be used in any application in which prior art electro-optic displays have been used. Thus, for example, the present displays may be used in electronic book readers, portable computers, tablet computers, cellular telephones, smart cards, signs, watches, shelf labels and flash drives.
  • BRIEF DESCRIPTION OF THE DRAWING
  • The sole FIGURE of the accompanying drawing is a graph showing the optical state readings obtained in Example 5 below.
  • DETAILED DESCRIPTION
  • As indicated above, the present invention has two principal aspects, the first relating to incorporation of non-diffusible ionic material into an adhesive layer and the second relating to the use of dialyzed or diafiltered adhesive material and/or binder in electrophoretic media and displays. The two principal aspects of the invention will mainly be discussed separately below, but it will readily be apparent that both aspects of the invention may be incorporated into a single physical display.
  • Part A: Non-Diffusible Ionic Material
  • As indicated above, in one aspect the present invention provides an electro-optic assembly comprising an electro-optic layer and an adhesive layer. The adhesive layer contains an ionic material, of which one ion cannot migrate through the adhesive layer while the other can. This type of ionic material prevents ions diffusing out of the adhesive layer and potentially damaging other layers (for example, organic semiconductor layers) into which the ions diffuse.
  • Ionic conduction in polymeric adhesive layers has been shown to occur by a “hopping” mechanism, in which dissociated free ions translate among ionic aggregates (ion pairs and higher aggregates), most of these aggregates being essentially neutral. In accordance with the present invention, only one of the anion and cation of the ionic material is capable of motion. The fixed ion is constrained to a single location, while the mobile ion is still free to migrate. An example of an appropriate ionic material a polymeric salt, for example, an ionic salt of a polymeric carboxylate. In this case the carboxylate ion is effectively immobile because it is attached to the polymer chain, and can only move with the polymer as a whole. The cationic counterion, on the other hand, can freely participate in hopping motions, and the rate at which it can move depends on the strength of the electrostatic interaction with the anionic carboxylate, the concentration of carboxylate-counterion aggregates in the adhesive medium, the viscosity of the medium, and the free energy of solvation of the counterion by the medium.
  • As in the ion doped adhesives described in the aforementioned U.S. Pat. No. 7,012,735, in the present invention large cations are advantageous, in that they have relatively low electrostatic energies of attraction to the ionic aggregate states, and therefore dissociate readily from them. As an example, a quaternary ammonium hydroxide could be used to neutralize the carboxylic functions on the polyurethane, leading to a quaternary ammonium carboxylate polymer capable of supporting ionic conduction as described above.
  • It is desirable that the ionic material be chosen such that the conductivity of the final adhesive layer after drying can be modified and adjusted by varying the carboxylic acid content of the polyurethane, and also by the cation used. For example, in the aforementioned system where a carboxylic group on the polyurethane is neutralized with a quaternary ammonium hydroxide, at a given carboxylic acid content, the conductivity would be expected to increase in the order:
  • tetramethylammonium<tetraethylammonium<tetrabutylammonium, etc.
  • Phosphonium salts could also be used, and should be somewhat more conductive than the nitrogen containing analogs because of the larger size of the central atom. Other cationic species (e.g., complex ions of metals) may also be useful for this purpose. Solubility of the ionic material in the adhesive is not an issue in this approach, since the ions are an intrinsic part of the medium and cannot therefore phase separate as a separate crystalline phase.
  • The acidic component of the polymeric adhesive may also be made more acidic by replacing a carboxylic acid component by a group with a higher dissociation constant, for example, a sulfate monoester, sulfonic acid, sulfinic acid, a phosphonic acid, phosphinic acid group or phosphate ester, as long as there is at least one dissociable proton present. Quaternary salts and other large cations would still be expected to be most useful as counter ions because of their large size, and relatively high degree of ionic dissociation in dried adhesive media of low polarity. Nitrogen-based acids could also be used if attached to sufficiently electron-withdrawing functions (e.g., RSO2—NH—SO2R)). In this case almost any mobile ion could be used, including tertiary ammonium, because the mobile ion will exist in the protonated form even in the dried adhesive. However, mobile ions based on larger amines (i.e., ones with longer alkyl tails) might still be preferable, because they are effectively larger in size and therefore the ion pairs comprising them would be more dissociable.
  • Alternatively, a carboxylate group on the adhesive could be used with a mobile ion that is not a strong Bronsted acid, i.e., which does not have an acidic proton, such as the quaternary cations discussed above.
  • Adhesive compositions in which a cation is the fixed ion can be constructed by using quaternary ammonium groups in the polymer backbone or as side chains, and preferably using large anions (e.g., hexafluorophosphate, tetrabutylborate, tetraphenylborate, etc.) as the mobile ions. The quaternary ammonium groups could be replaced by phosphonium, sulfonium or other cationic groups without dissociable hydrogen, including those formed by complexation with metallic cations. Examples of the latter include polyether/lithium ion inclusion complexes, especially cyclic polyethers (e.g. 18-crown-6) or polyamine complexes with transition metal ions. In this case the anionic mobile ion could include those types of ions listed above, plus more strongly basic materials such as carboxylates or even phenolates.
  • Alternative fixed cation adhesive materials include polymers containing repeating units derived from basic monomers, for example poly(vinylpyridine), poly(β-dimethylaminoethyl acrylate), etc. and copolymers containing such groups, in conjunction with mobile anions that are not good Bronsted acceptors (e.g., sulfonates, sulfates, hexafluorophosphate, tetrafluoroborate, bis(methanesulfonyl)imidate, phosphates, phosphonates, etc.). Quaternary salts derived from such amino monomers may also be used, for example poly(N-methyl or benzyl(vinylpyridinium)), poly(N-alkyl (or alkaryl)-N′-vinylimidazolium), and poly(β-trimethylammonioethyl)acrylate or methacrylate) salts, as well as vinyl copolymers comprising these ionic groups. As before, larger mobile ions are preferred.
  • These chemical modification techniques are not restricted to polyurethanes but can be applied to any polymer of suitable structure. For example, vinyl-based polymers can contain either anions or cation fixed ions.
  • Part B : Dialyzed or Diafiltered Adhesive Material and/or Binder
  • As already noted, one aspect of the present invention reduces or eliminates problems caused by migration of ionic dopants from adhesive layers into other layers of electro-optic displays, especially damage to active matrix backplanes comprising transistors made from certain organic semiconductors. However, it has now been found that the causes of these problems are not confined to ionic dopants but include other fugitive species present in prior art adhesive and binder compositions, which can migrate from the adhesive or binder layer to other layers of the electro-optic display in a manner similar to the ionic dopants. One such fugitive species of particular concern is N-methylpyrrolidone (NMP), which is used as a solvent in the preparation of polyurethanes. Other fugitive species which may be of concern in some cases include other solvents used in the preparation of polyurethanes, and dialyzable poorly characterized low molecular weight molecules from the polymerization reaction. It has been found that removing NMP by careful drying of the adhesive layer improves that layer's storage stability. Dialysis of the lamination adhesive removes both NMP and also other low molecular weight materials and is even more effective. The non-diffusible ionic material adhesive compositions of the present invention can be subjected to dialysis, since electrical neutrality prevents gross separation of the fixed and mobile ions, and after dialysis the adhesive material contains little or no diffusible materials. The present adhesives have therefore been found to be particularly effective in reducing the deleterious effects of the lamination adhesive on the performance of backplanes containing organic semiconductors. Diafiltration can also be used instead of dialysis.
  • As already noted, the non-diffusible ionic material adhesive materials of the present invention can be purified by dialysis or diafiltration. However, it may also be useful to synthesize these adhesive materials by dialysis. For example an aqueous solution of a polyamine or polyether could be partially transformed into a cationic complex by dialysis of the polymer solution in a solution of the appropriate water-soluble metal salt.
  • Dialysis or diafiltration can also be used to remove NMP and other fugitive species from conventional polyurethane adhesives before such adhesives are mixed with conventional ionic dopants. Thus, as already noted, in its second principal aspect this invention provides an electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprising a polymeric adhesive material which has been subjected to dialysis or diafiltration to remove organic species having a molecular weight less than about 3,500. Such dialysis or diafiltration may be used be remove, among other species, NMP, tetrahydrofuran (THF) and acetone. Similarly, the second aspect of the present invention also provides an electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprising a polymeric adhesive material having a content of N-methylpyrrolidone not exceeding about 500 ppm, preferably not exceeding about 200 ppm, and desirably not exceeding about 100 ppm, in all cases based upon the total weight of the adhesive layer and layer of electro-optic material.
  • The second aspect of the present invention also provides an electrophoretic medium comprising a continuous phase and a discontinuous phase, the discontinuous phase comprising a plurality of droplets, each of which comprises a suspending fluid and at least one particle disposed within the suspending fluid and capable of moving through the fluid upon application of an electric field to the electrophoretic medium, the continuous phase surrounding and encapsulating the discontinuous phase and comprising a polymeric binder which has been subjected to dialysis or diafiltration to remove organic species having a molecular weight less than about 3,500. The electrophoretic medium may be either of the encapsulated or polymer-dispersed type, i.e., there may or may not be a capsule wall between each droplet and the binder. The second aspect of the present invention also provides an electrophoretic medium comprising a continuous phase and a discontinuous phase, the discontinuous phase comprising a plurality of droplets, each of which comprises a suspending fluid and at least one particle disposed within the suspending fluid and capable of moving through the fluid upon application of an electric field to the electrophoretic medium, the continuous phase surrounding and encapsulating the discontinuous phase and comprising a polymeric binder having a total content of N-methylpyrrolidone, tetrahydrofuran and acetone not exceeding about 1000 ppm, preferably not exceeding about 400 ppm and desirably not exceeding about 200 ppm, in all cases based upon the weight of the electrophoretic medium (i.e., of the combination of the continuous and discontinuous phases).
  • As already indicated, the second aspect of the present invention may be used to remove NMP and possibly other fugitive species from the lamination adhesive and/or the binder used in an electro-optic display. In many cases, removal of fugitive species from the binder is of greater importance than removal from the lamination adhesive. The preparation of a lamination adhesive layer typically involves coating a flowable form of the adhesive on to a release sheet, then drying the layer of adhesive so that a coherent layer of adhesive is formed on the release sheet. High temperature and low coating speeds during the drying step suffice to drive off a large proportion of volatile organic species; for example, it has been found that a lamination adhesive coated at 50,000 ppm of NMP had only 200 ppm of NMP after drying. Furthermore, since only layers present during drying are the lamination adhesive and the release sheet (lamination of the adhesive to the electro-optic medium takes place only after the drying step), the choice of drying conditions can be based only upon the properties of the lamination adhesive itself, and does not need to take into account the properties of the electro-optic medium. In contrast, the binder used in an electrophoretic medium is typically admixed with the discontinuous phase of the medium to form a slurry which is then coated and dried to form the electrophoretic medium. Hence, in this case the drying conditions must take account of the properties of the discontinuous phase, and in particular concerns about simultaneous removal of the volatile discontinuous phase solvent. Finally, from a quality control point of view, removing all materials having the potential to damage any backplane with which an electro-optic medium may be expected to come into contact represents a good insurance policy, so that the number of unknown constituents (whose concentration could change with no knowledge or control) is kept to a minimum; obviously, as a matter of good manufacturing process, use of pure materials of known composition is highly desirable.
  • Both dialysis and diafiltration are well known ways of purifying suspensions of colloids and polymers. In both techniques, the suspension is confined by a semi-permeable membrane on the opposed side of which is a washing solution, typically water or a buffer solution. Molecules that can pass through the membrane and are soluble in the washing solution equilibrate between the two regions of the apparatus, and are removed from the suspension by exchange of the washing solution. Typically, the membrane is made of a material that allows selective passage of low molecular weight materials, and water is commonly employed as the solvent; in the present invention a membrane with a molecular-weight cutoff (MWCO) of about 3.5 kD has been found useful. Since NMP is a water-soluble solvent, these techniques are well suited for the removal of this contaminant. At the same time, other soluble materials, some with potentially deleterious properties, can also be removed. There is no requirement that the species to be removed be appreciably volatile, as is the case for removal by drying. By adjusting the properties of the membrane, the class of molecules removed can be changed. For example, if in a particular lamination adhesive or binder the presence of water-soluble oligomeric polymer fragments were a problem, a membrane with a higher MWCO could be used to remove such fragments; a variety of semi-permeable membranes with various MWCO's are available commercially.
  • Either dialysis or diafiltration can be used in the present process, but for commercial production diafiltration is usually preferred. Dialysis is a simple equilibration process, while diafiltration employs high flow conditions and high trans-membrane pressures to accelerate mass transport though the membrane. Diafiltration is substantially faster than dialysis, and can be employed under conditions that prevent dilution of the material being purified, as is often the case in dialysis. Diafiltration is a readily scalable process, and both laboratory scale and production scale equipment is available at reasonable cost. Diafiltration is a well established industrial procedure, widely used in the biochemical and other industries.
  • The present inventors have shown that both dialysis and diafiltration are effective in the removal of NMP from suspensions of commercial polyurethane latices. It has been found empirically that dialysis and diafiltration of polyurethane latices using a membrane with a low MWCO (3.5 kD) can reduce the NMP content by more than an order of magnitude in a few hours. For example, the NMP content of one polyurethane binder was reduced from about 14% (140,000 ppm) to about 500 ppm by diafiltration. When using dialysis, the efficiency of NMP removal may be limited by dilution of the latex, which made the latex difficult to coat, especially in the case of a lamination adhesive. The latex could be concentrated by evaporation of the excess water under reduced pressure, but this was an awkward procedure. Examination of the molecular weight distribution of the purified polyurethane latex showed that it was essentially identical to the starting material, i.e., no polymer was lost during dialysis. When dialysed material was used in the place of undialysed binder and lamination adhesive, a number of advantages were observed.
  • First, the degradation in the performance of organic semiconductor backplanes was largely eliminated. The same result could be obtained if only the binder, and not the lamination adhesive, was dialysed. If the binder dialysis was omitted, however, severe degradation in organic semiconductor device performance was experienced.
  • A second advantage was that the cell-gap resistance (a measure of the electrical conductivity of the front plane laminate) was higher, typically by about 50 per cent, using dialysed materials. A higher cell-gap resistance puts fewer demands on the on-state conductivity of the operating transistor (that is, a lower on-off ratio is permissible). This is a particularly important characteristic for organic semiconductor transistors, the on-off ratio of which is typically not as high as for inorganic transistors.
  • A third advantage was a small improvement in the electro-optical properties of the electrophoretic medium produced from the dialyzed latex. As illustrated in Example 5 below, use of dialysed polyurethane latex resulted in about a 2L* (using the usual CIE definition of L*) improvement in dynamic range (the difference between the extreme white and dark electro-optic states of the medium) relative to use of undialysed material.
  • The following Examples are now given, though by way of illustration only, to show details of preferred reagents, conditions and techniques used in the present invention.
  • EXAMPLE 1 Synthesis of TMXDI-PPO Polyurethane with Tetrabutylammonium Hydroxide Neutralization
  • The polyurethane prepared in this Example is similar to the prior art polyurethane produced in Example 2 below, except that it has a higher acid content.
  • A prepolymer was prepared in a three-necked round bottom flask equipped with a magnetic stirrer, a condenser, and a nitrogen inlet. The reaction was carried out under nitrogen. Tetramethylxylene diisocyanate (TMXDI, supplied by Aldrich Chemical Company, 16.34 g, 0.067 mole), poly(propylene glycol) diol (supplied by Aldrich Chemical Company, average Mn ca. 2000, 33.5 g, 0.0168 mole), and dibutyltin dilaurate (supplied by Aldrich Chemical Company, 0.04 g) were charged into the flask and the mixture was heated at 90° C. in an oil bath for 2 hours. Afterwards, a solution of 2,2-bis(hydroxymethyl)propionic acid (from Aldrich, 3.35 g, 0.025 mol) in 1-methyl-2-pyrrolidinone (from Aldrich, 8.5 g) was added to the flask and the reaction allowed to proceed at 90° C. for another 2 hours to obtain NCO-terminated prepolymer. The temperature of the reaction mixture was then lowered to 70° C. Separately, tetrabutylammonium hydroxide (NBu4OH) (from Aldrich, 6.15 g, 0.0237 mol) and de-ionized water (100 g) were charged into a jacketed 500 mL glass reactor equipped with a mechanical stirrer, a thermometer, and a nitrogen inlet, and the resultant mixture was heated to 35° C. under nitrogen. The prepolymer mixture was then slowly added to the aqueous NBu4OH solution to convert the prepolymer to a water-borne dispersion under mechanical stirring and nitrogen atmosphere. A chain extension reaction was carried out after the dispersing step with hexamethylenediamine (from Aldrich) dissolved in a small amount of water at 35° C. The end point of the chain extension reaction was determined from pH measurement. Finally, the resultant dispersion was heated to 50° C. for one hour to make sure that any residual isocyanate groups were consumed by water.
  • EXAMPLE 2 Synthesis of TMXDI-PPO Polyurethane with Triethylamine Neutralization (Control)
  • Example 1 was repeated up to the point at which an NCO-terminated prepolymer was obtained and the temperature of the reaction mixture lowered to 70° C. Thereafter triethylamine (from Aldrich, 2.4 g, 0.0237 mole) was added slowly over a period of 30 minutes to neutralize the carboxylic acid. The reaction mixture was then slowly added to de-ionized water (100 g) at 35° C. in a jacketed 500 mL glass reactor under mechanical stirring and nitrogen atmosphere to convert the prepolymer to a water-borne dispersion. The chain extension reaction and the final heating of the dispersion to 50° C. were carried out in the same manner as in Example 1.
  • EXAMPLE 3 Preparation of Experimental Single Pixel Displays from the Materials Prepared in Examples 1 and 2
  • The polyurethanes prepared in Examples 1 and 2 above were separately coated on to metallized release film in a (dried) thickness of about 20 μm. Drying of the coated polymeric films was carried out in a belt-transport drying oven at 60° C. and a transport rate of 1 ft/min (about 5.1 mm/sec); these conditions are known to reduce the content of NMP to a very low level. Separately, an electrophoretic medium was prepared substantially as described in Example 4 of U.S. Pat. No. 7,002,728 and coated on to the indium tin oxide (ITO) coated surface of a 5 mil (127 μm) poly(ethylene terephthalate) (PET) film coated on one surface with ITO. The two sub-assemblies were laminated to each other with the electrophoretic layer in contact with the lamination adhesive to form a front plane laminate as described in the aforementioned U.S. Pat. No. 6,982,178. The release sheet was peeled from the front plane laminate and the remaining layers laminated to experimental single pixel 2 inch (51 mm) square backplanes, comprising a layer of carbon black on a PET film, to form experimental single pixel displays. No addition dopant was incorporated into either adhesive coating. The experimental displays were conditioned for 1 day at 50 per cent relative humidity (as discussed in several of the aforementioned E Ink patents and applications, the electro-optic properties of electrophoretic displays vary with the moisture content of the electrophoretic layer, and hence it is desirable to condition test specimens under standard conditions prior to testing).
  • The electro-optic properties of the experimental displays were then tested by driving them to their black and white optical states using 250 millisecond pulses at various voltages, measuring the reflectances of the black and white optical states, and converting these reflectances to conventional L* values, where L* has the usual CIE definition:

  • L*=116(R/R 0)1/3−16,
  • where R is the reflectance and R0 is a standard reflectance value. Table 1 below shows the dynamic range (the difference between the L* values of the black and white optical states) achieved at various voltages:
  • TABLE 1
    Lamination adhesive
    neutralizing agent Voltage (V) Dynamic range (L*)
    Triethylamine (Control) 7.5 7.1
    10 14.1
    12.5 20.0
    15 24.4
    Tetrabutylammonium 7.5 21.5
    hydroxide (Present Invention)
    10 30.7
    12.5 35.4
    15 37.7
  • It will be seen from Table 1 that the lamination adhesive of the present invention showed substantially greater dynamic range at all drive voltages than the control adhesive. This improvement is consistent with that expected from a difference in conductivity, and is similar to that found using a prior art doped adhesive of lower acid content. The control adhesive, neutralized with triethylamine, shows the electro-optic response expected for a very resistive lamination adhesive. Visual inspection of the displays during operation showed that the display with the control adhesive showed only a small amount of blooming at the edge of the display, whereas the display using the adhesive of the present invention displayed a large amount of blooming. A high degree of blooming is also consistent with an adhesive of high conductivity.
  • The experimental displays were also subjected to low temperature testing. As discussed in several of the aforementioned E Ink patents and applications, the electro-optic performance of electrophoretic displays tends to fall off rapidly at low temperatures, at least partially because the conductivity of lamination adhesives falls with temperature. To determine the low temperature behavior of the experimental display of the present invention, the display was driven at temperatures from +25 to −25° C. using 15 V pulses of either 250 or 500 millisecond duration, and the dynamic range was determined, using reflectance values taken 2 minutes after the end of the drive pulse. (This 2 minute pause before taking the reflectance value allows certain short-term effects which affect the reflectance value to dissipate.) The reflectance values obtained were converted to a dynamic range value in the same way as before, and the results are shown in Table 2 below.
  • TABLE 2
    Temperature Drive pulse
    ° C. (ms)) Dynamic range (L*)
    25 250 35.1
    15 250 35.8
    5 250 33.4
    −5 250 25.5
    −5 500 31.2
    −15 500 20.2
    −25 500 4.4
  • From the data in Table 2, it will be seen that the adhesive of the present invention provides adequate performance down to about −10° C., provided that pulse length compensation is used, i.e., provided the drive pulses are lengthened at low temperatures. This low temperature performance is comparable to that of a highly doped prior art lamination adhesive.
  • EXAMPLE 4 Purification of Lamination Adhesive of the Present Invention by Dialysis
  • A sample (49.3 g, 35% wt. solids) of the lamination adhesive prepared in Example 1 above was placed in a tube of dialysis membrane (Fisher (Registered Trade Mark) regenerated cellulose membrane, MWCO 3500). After closing both ends of the tubing with clamps, the tubing was immersed in a continually replenished, stirred tank of water for about 4 hours. At then end of this time, 61.6 g of material was recovered, with a solids content of 29.5% (95% recovery). Initially, the NMP content was 4.4%; after dialysis, the content was 1.4%. The NMP content may be used as a surrogate for the removal of other water-soluble, low molecular weight materials.
  • Preliminary long term storage tests on displays using the dialyzed lamination adhesive prepared in Example 4 above with prior art lamination adhesives, both dialyzed and non-dialyzed, and proprietary organic semiconductor backplanes, indicated that the dialyzed lamination adhesive of the present invention had substantially better long term storage characteristics than the prior art adhesives.
  • EXAMPLE 5 Use of Dialyzed Binder and Lamination Adhesive in Electrophoretic Displays
  • A polyurethane latex was synthesized substantially as described in Example 2 of U.S. Patent Application Publication No. 2008/0074730, and was used as a binder in experiments described below. A second polyurethane latex was synthesized substantially as described in Example 2 of U.S. Patent Application Publication No. 2005/0107564 and was used as the lamination adhesive in these experiments.
  • Experimental single pixel displays were prepared substantially as described in Example 7 of U.S. Pat. No. 7,002,728, but using the aforementioned binder and lamination adhesive; the lamination adhesive was doped with 180 ppm of tetrabutylammonium hexafluorophosphate. Four sets of the experimental displays were produced, as follows:
      • (A) Neither binder nor lamination adhesive was dialyzed;
      • (B) The binder was dialyzed substantially as described in Example 4 above, but the lamination adhesive was not dialyzed;
      • (C) The binder was not dialyzed but the lamination adhesive was dialyzed substantially as described in Example 4 above; and
      • (D) Both the binder and the lamination adhesive were dialyzed substantially as described in Example 4 above.
  • The electro-optic properties of the four sets of experimental displays were then tested substantially as described in Example 7 of U.S. Pat. No. 7,002,728, but using 300 millisecond pulses of ±15V, and the extreme white and dark state reflectances were measured and converted to CIE L* units. The results are shown in the sole FIGURE of the accompanying drawings. In each set of readings, the left-hand bar represents the extreme white state of the display, the center bar represents the extreme dark state, and the right-hand bar represents the dynamic range (i.e., the difference between the extreme white and dark states, measured in L* units).
  • It will be seen from the FIGURE that the dialysis of the binder and lamination adhesive had no adverse effect on the electro-optic properties of the displays. Indeed, the two displays (B and D) in which the binder was dialyzed showed an improved white state, the displays C and D showed an improved dark state (improvement of the dark state is of course represented by a lower L* value). The display D, in which both the binder and the lamination adhesive were dialyzed, showed the greatest dynamic range of the four sets of displays.
  • The electro-optic testing was repeated using ±15V pulses of 100 and 500 millisecond duration, and ±10V, 100, 300 and 500 millisecond pulses. In all cases, the results obtained were consistent with those shown in the FIGURE.
  • When front plane laminates containing the binder and lamination adhesive combinations mentioned under (A)-(D) above were laminated to backplanes using organic transistors, it was observed that the front plane laminates containing undialyzed binder caused rapid degradation of the organic transistors whereas front plane laminates containing dialyzed binder did not. A similar but smaller effect was noted using dialyzed lamination adhesive.
  • From the foregoing, it will be seen that the present invention can provide lamination adhesives which provide electro-optic characteristics and low temperature performance comparable to those of prior art adhesives while avoiding the use of fugitive ionic species which can damage certain backplanes, and potentially lead to other problems. Furthermore, the present invention can provide
  • It will be apparent to those skilled in the art that numerous changes and modifications can be made in the specific embodiments of the invention described above without departing from the scope of the invention. Accordingly, the whole of the foregoing description is to be interpreted in an illustrative and not in a limitative sense.

Claims (27)

1. An electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprising a polymeric adhesive material and an ionic material, the ionic material having one of its cation and anion fixed to the polymeric adhesive material and the other of its cation and anion free to migrate through the polymeric adhesive material, the ionic material reducing the volume resistivity of the polymeric adhesive material and not being removed by heating the polymeric adhesive material to about 50° C.
2. An electro-optic assembly according to claim 1 wherein the ionic material comprises a quaternary ammonium or phosphonium cation and a carboxylate anion fixed to the polymeric adhesive material.
3. An electro-optic assembly according to claim 1 wherein the polymeric adhesive material comprises a polyurethane.
4. An electro-optic assembly according to claim 1 wherein the ionic material comprises a quaternary ammonium or phosphonium cation fixed to the polymeric adhesive material and a hexafluorophosphate, tetrabutylborate or tetraphenylborate anion.
5. An electro-optic assembly according to claim 1 wherein the ionic material comprises repeating units derived from a basic monomer and a mobile anion selected from the group comprising sulfonates, sulfates, hexafluorophosphates, tetrafluoroborates, bis(methanesulfonyl)imidate, phosphates and phosphonates.
6. An electro-optic assembly according to claim 5 wherein the basic monomer comprises any one or more of vinylpyridine, β-dimethylaminoethyl acrylate, N-methyl or benzyl(vinylpyridine), N-alkyl or alkaryl-N′-vinylimidazole, and β-(trimethylammonioethyl)acrylate or methacrylate.
7. An electro-optic assembly according to claim 1 wherein the electro-optic material comprises a rotating bichromal member or electrochromic material.
8. An electro-optic assembly according to claim 1 wherein the electro-optic material comprises an electrophoretic material comprising a plurality of electrically charged particles disposed in a fluid and capable of moving through the fluid under the influence of an electric field.
9. An electro-optic assembly according to claim 8 wherein the electrically charged particles and the fluid are confined within a plurality of capsules or microcells.
10. An electro-optic assembly according to claim 8 wherein the electrically charged particles and the fluid are present as a plurality of discrete droplets surrounded by a continuous phase comprising a polymeric material.
11. An electro-optic display according to claim 8 wherein the fluid is gaseous.
12. An electro-optic display, front plane laminate, inverted front plane laminate or double release film comprising an electro-optic assembly according to claim 1.
13. An electronic book reader, portable computer, tablet computer, cellular telephone, smart card, sign, watch, shelf label or flash drive comprising an electro-optic display according to claim 12.
14. An electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprising a polymeric adhesive material which has been subjected to dialysis or diafiltration to remove organic species having a molecular weight less than about 3,500.
15. An electro-optic assembly comprising an adhesive layer and a layer of electro-optic material, the adhesive layer comprising a polymeric adhesive material having a content of N-methylpyrrolidone not exceeding about 500 ppm based upon the total weight of the adhesive layer and layer of electro-optic material.
16. An electro-optic assembly according to claim 15 wherein the polymeric adhesive material comprises a polyurethane.
17. An electro-optic assembly according to claim 15 having a content of N-methylpyrrolidone not exceeding about 200 ppm.
18. An electro-optic assembly according to claim 17 having a content of N-methylpyrrolidone not exceeding about 100 ppm.
19. An electro-optic assembly according to claim 15 wherein the electro-optic material comprises a rotating bichromal member or electrochromic material.
20. An electro-optic assembly according to claim 15 wherein the electro-optic material comprises an electrophoretic material comprising a plurality of electrically charged particles disposed in a fluid and capable of moving through the fluid under the influence of an electric field.
21. An electro-optic assembly according to claim 20 wherein the electrically charged particles and the fluid are confined within a plurality of capsules or microcells.
22. An electro-optic assembly according to claim 20 wherein the electrically charged particles and the fluid are present as a plurality of discrete droplets surrounded by a continuous phase comprising a polymeric material.
23. An electro-optic display according to claim 20 wherein the fluid is gaseous.
24. An electro-optic display, front plane laminate, inverted front plane laminate or double release film comprising an electro-optic assembly according to claim 15.
25. An electronic book reader, portable computer, tablet computer, cellular telephone, smart card, sign, watch, shelf label or flash drive comprising an electro-optic display according to claim 24.
26. An electrophoretic medium comprising a continuous phase and a discontinuous phase, the discontinuous phase comprising a plurality of droplets, each of which comprises a suspending fluid and at least one particle disposed within the suspending fluid and capable of moving through the fluid upon application of an electric field to the electrophoretic medium, the continuous phase surrounding and encapsulating the discontinuous phase and comprising a polymeric binder which has been subjected to dialysis or diafiltration to remove organic species having a molecular weight less than about 3,500.
27. An electrophoretic medium comprising a continuous phase and a discontinuous phase, the discontinuous phase comprising a plurality of droplets, each of which comprises a suspending fluid and at least one particle disposed within the suspending fluid and capable of moving through the fluid upon application of an electric field to the electrophoretic medium, the continuous phase surrounding and encapsulating the discontinuous phase and comprising a polymeric binder having a content of N-methylpyrrolidone not exceeding about 1000 ppm based upon the weight of the electrophoretic medium.
US12/264,696 2007-11-14 2008-11-04 Electro-optic assemblies, and adhesives and binders for use therein Abandoned US20090122389A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US98787607P true 2007-11-14 2007-11-14
US12/264,696 US20090122389A1 (en) 2007-11-14 2008-11-04 Electro-optic assemblies, and adhesives and binders for use therein

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US12/264,696 US20090122389A1 (en) 2007-11-14 2008-11-04 Electro-optic assemblies, and adhesives and binders for use therein
US15/053,283 US9964831B2 (en) 2007-11-14 2016-02-25 Electro-optic assemblies, and adhesives and binders for use therein
US15/261,151 US10036930B2 (en) 2007-11-14 2016-09-09 Electro-optic assemblies, and adhesives and binders for use therein

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US15/053,283 Division US9964831B2 (en) 2007-11-14 2016-02-25 Electro-optic assemblies, and adhesives and binders for use therein

Publications (1)

Publication Number Publication Date
US20090122389A1 true US20090122389A1 (en) 2009-05-14

Family

ID=40623440

Family Applications (3)

Application Number Title Priority Date Filing Date
US12/264,696 Abandoned US20090122389A1 (en) 2007-11-14 2008-11-04 Electro-optic assemblies, and adhesives and binders for use therein
US15/053,283 Active 2029-09-07 US9964831B2 (en) 2007-11-14 2016-02-25 Electro-optic assemblies, and adhesives and binders for use therein
US15/261,151 Active 2029-05-13 US10036930B2 (en) 2007-11-14 2016-09-09 Electro-optic assemblies, and adhesives and binders for use therein

Family Applications After (2)

Application Number Title Priority Date Filing Date
US15/053,283 Active 2029-09-07 US9964831B2 (en) 2007-11-14 2016-02-25 Electro-optic assemblies, and adhesives and binders for use therein
US15/261,151 Active 2029-05-13 US10036930B2 (en) 2007-11-14 2016-09-09 Electro-optic assemblies, and adhesives and binders for use therein

Country Status (8)

Country Link
US (3) US20090122389A1 (en)
EP (1) EP2217440B1 (en)
JP (4) JP5679816B2 (en)
KR (5) KR20160106208A (en)
CN (1) CN101855083B (en)
HK (1) HK1145478A1 (en)
TW (1) TWI451966B (en)
WO (1) WO2009064642A1 (en)

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7679814B2 (en) 2001-04-02 2010-03-16 E Ink Corporation Materials for use in electrophoretic displays
US7999787B2 (en) 1995-07-20 2011-08-16 E Ink Corporation Methods for driving electrophoretic displays using dielectrophoretic forces
US8040594B2 (en) 1997-08-28 2011-10-18 E Ink Corporation Multi-color electrophoretic displays
US8054526B2 (en) 2008-03-21 2011-11-08 E Ink Corporation Electro-optic displays, and color filters for use therein
US20110286080A1 (en) * 2010-04-02 2011-11-24 E Ink Corporation Electrophoretic media, and materials for use therein
US8098418B2 (en) 2009-03-03 2012-01-17 E. Ink Corporation Electro-optic displays, and color filters for use therein
US8270064B2 (en) 2009-02-09 2012-09-18 E Ink Corporation Electrophoretic particles, and processes for the production thereof
US8314784B2 (en) 2008-04-11 2012-11-20 E Ink Corporation Methods for driving electro-optic displays
US8322045B2 (en) * 2002-06-13 2012-12-04 Applied Materials, Inc. Single wafer apparatus for drying semiconductor substrates using an inert gas air-knife
US8363299B2 (en) 2002-06-10 2013-01-29 E Ink Corporation Electro-optic displays, and processes for the production thereof
US8390918B2 (en) 2001-04-02 2013-03-05 E Ink Corporation Electrophoretic displays with controlled amounts of pigment
US8389381B2 (en) 2002-04-24 2013-03-05 E Ink Corporation Processes for forming backplanes for electro-optic displays
US8553012B2 (en) 2001-03-13 2013-10-08 E Ink Corporation Apparatus for displaying drawings
US8654436B1 (en) 2009-10-30 2014-02-18 E Ink Corporation Particles for use in electrophoretic displays
US8754859B2 (en) 2009-10-28 2014-06-17 E Ink Corporation Electro-optic displays with touch sensors and/or tactile feedback
US9075280B2 (en) 2002-09-03 2015-07-07 E Ink Corporation Components and methods for use in electro-optic displays
US9122143B2 (en) 2012-06-07 2015-09-01 Mindflow Llc Dynamically variable graphic material using electrostatically attracted particles
US9293511B2 (en) 1998-07-08 2016-03-22 E Ink Corporation Methods for achieving improved color in microencapsulated electrophoretic devices
US20160085132A1 (en) * 2014-09-10 2016-03-24 E Ink Corporation Colored electrophoretic displays
US9465206B1 (en) * 2014-02-04 2016-10-11 Amazon Technologies, Inc. Adhesive/sealing material for an electrowetting device
US9506243B1 (en) 2014-03-20 2016-11-29 E Ink Corporation Thermally-responsive film
WO2016191673A1 (en) 2015-05-27 2016-12-01 E Ink Corporation Methods and circuitry for driving display devices
US9529240B2 (en) 2014-01-17 2016-12-27 E Ink Corporation Controlled polymeric material conductivity for use in a two-phase electrode layer
US9671635B2 (en) 2014-02-07 2017-06-06 E Ink Corporation Electro-optic display backplane structures with drive components and pixel electrodes on opposed surfaces
US9715155B1 (en) 2013-01-10 2017-07-25 E Ink Corporation Electrode structures for electro-optic displays
US9726957B2 (en) 2013-01-10 2017-08-08 E Ink Corporation Electro-optic display with controlled electrochemical reactions
US9835925B1 (en) 2015-01-08 2017-12-05 E Ink Corporation Electro-optic displays, and processes for the production thereof
US10175550B2 (en) 2014-11-07 2019-01-08 E Ink Corporation Applications of electro-optic displays
US10190743B2 (en) 2012-04-20 2019-01-29 E Ink Corporation Illumination systems for reflective displays
US10254621B2 (en) 2017-11-03 2019-04-09 E Ink Corporation Electro-optic displays, and processes for the production thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2373300B1 (en) 2011-12-14 2012-12-20 Soro Internacional, S.A. Dishwashing detergent.

Citations (90)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US719008A (en) * 1902-10-20 1903-01-27 Int Harvester Co Folding frame for grinders.
US3792308A (en) * 1970-06-08 1974-02-12 Matsushita Electric Ind Co Ltd Electrophoretic display device of the luminescent type
US3870517A (en) * 1969-10-18 1975-03-11 Matsushita Electric Ind Co Ltd Color image reproduction sheet employed in photoelectrophoretic imaging
US5745094A (en) * 1994-12-28 1998-04-28 International Business Machines Corporation Electrophoretic display
US5891366A (en) * 1994-05-10 1999-04-06 Robert Bosch Gmbh Anisotropically conducting adhesive, and process for producing an anisotropically conducting adhesive
US6017584A (en) * 1995-07-20 2000-01-25 E Ink Corporation Multi-color electrophoretic displays and materials for making the same
US6054071A (en) * 1998-01-28 2000-04-25 Xerox Corporation Poled electrets for gyricon-based electric-paper displays
US6055091A (en) * 1996-06-27 2000-04-25 Xerox Corporation Twisting-cylinder display
US6171522B1 (en) * 1996-12-30 2001-01-09 Hydro-Qu{acute over (e)}bec Heterocyclic aromatic anion salts, and their uses as ionic conducting materials
US6172798B1 (en) * 1998-04-27 2001-01-09 E Ink Corporation Shutter mode microencapsulated electrophoretic display
US6177921B1 (en) * 1997-08-28 2001-01-23 E Ink Corporation Printable electrode structures for displays
US6184856B1 (en) * 1998-09-16 2001-02-06 International Business Machines Corporation Transmissive electrophoretic display with laterally adjacent color cells
US6184331B1 (en) * 1995-05-25 2001-02-06 Mearthane Products Corporation Preparation of conductive polyurethanes using a conductive quasi-solution
US20020027635A1 (en) * 2000-09-05 2002-03-07 Fuji Xerox Co., Ltd Display device
US6377387B1 (en) * 1999-04-06 2002-04-23 E Ink Corporation Methods for producing droplets for use in capsule-based electrophoretic displays
US6376828B1 (en) * 1998-10-07 2002-04-23 E Ink Corporation Illumination system for nonemissive electronic displays
US6504524B1 (en) * 2000-03-08 2003-01-07 E Ink Corporation Addressing methods for displays having zero time-average field
US6506438B2 (en) * 1998-12-15 2003-01-14 E Ink Corporation Method for printing of transistor arrays on plastic substrates
US6512354B2 (en) * 1998-07-08 2003-01-28 E Ink Corporation Method and apparatus for sensing the state of an electrophoretic display
US6515649B1 (en) * 1995-07-20 2003-02-04 E Ink Corporation Suspended particle displays and materials for making the same
US6518949B2 (en) * 1998-04-10 2003-02-11 E Ink Corporation Electronic displays using organic-based field effect transistors
US6521489B2 (en) * 1999-07-21 2003-02-18 E Ink Corporation Preferred methods for producing electrical circuit elements used to control an electronic display
US6531997B1 (en) * 1999-04-30 2003-03-11 E Ink Corporation Methods for addressing electrophoretic displays
US6538801B2 (en) * 1996-07-19 2003-03-25 E Ink Corporation Electrophoretic displays using nanoparticles
US6545291B1 (en) * 1999-08-31 2003-04-08 E Ink Corporation Transistor design for use in the construction of an electronically driven display
US6672921B1 (en) * 2000-03-03 2004-01-06 Sipix Imaging, Inc. Manufacturing process for electrophoretic display
USD485294S1 (en) * 1998-07-22 2004-01-13 E Ink Corporation Electrode structure for an electronic display
US6680725B1 (en) * 1995-07-20 2004-01-20 E Ink Corporation Methods of manufacturing electronically addressable displays
US6683333B2 (en) * 2000-07-14 2004-01-27 E Ink Corporation Fabrication of electronic circuit elements using unpatterned semiconductor layers
US6693620B1 (en) * 1999-05-03 2004-02-17 E Ink Corporation Threshold addressing of electrophoretic displays
US6704133B2 (en) * 1998-03-18 2004-03-09 E-Ink Corporation Electro-optic display overlays and systems for addressing such displays
US6710540B1 (en) * 1995-07-20 2004-03-23 E Ink Corporation Electrostatically-addressable electrophoretic display
US20040060635A1 (en) * 2002-09-25 2004-04-01 Heinrich Diepers Method of producing an adhesive bond
US6839158B2 (en) * 1997-08-28 2005-01-04 E Ink Corporation Encapsulated electrophoretic displays having a monolayer of capsules and materials and methods for making the same
US6842657B1 (en) * 1999-04-09 2005-01-11 E Ink Corporation Reactive formation of dielectric layers and protection of organic layers in organic semiconductor device fabrication
US6842167B2 (en) * 1997-08-28 2005-01-11 E Ink Corporation Rear electrode structures for displays
US6842279B2 (en) * 2002-06-27 2005-01-11 E Ink Corporation Illumination system for nonemissive electronic displays
US20050012980A1 (en) * 2003-05-02 2005-01-20 E Ink Corporation Electrophoretic displays with controlled amounts of pigment
US20050024353A1 (en) * 2001-11-20 2005-02-03 E Ink Corporation Methods for driving electro-optic displays
US6865010B2 (en) * 2001-12-13 2005-03-08 E Ink Corporation Electrophoretic electronic displays with low-index films
US6864875B2 (en) * 1998-04-10 2005-03-08 E Ink Corporation Full color reflective display with multichromatic sub-pixels
US6866760B2 (en) * 1998-08-27 2005-03-15 E Ink Corporation Electrophoretic medium and process for the production thereof
US6870661B2 (en) * 2001-05-15 2005-03-22 E Ink Corporation Electrophoretic displays containing magnetic particles
US6870657B1 (en) * 1999-10-11 2005-03-22 University College Dublin Electrochromic device
US20050062714A1 (en) * 2003-09-19 2005-03-24 E Ink Corporation Methods for reducing edge effects in electro-optic displays
US6982178B2 (en) * 2002-06-10 2006-01-03 E Ink Corporation Components and methods for use in electro-optic displays
US6987603B2 (en) * 2003-01-31 2006-01-17 E Ink Corporation Construction of electrophoretic displays
US20060017069A1 (en) * 2002-02-18 2006-01-26 Robert Bergmann Electronic component with an adhesive layer and method for the production thereof
US6995550B2 (en) * 1998-07-08 2006-02-07 E Ink Corporation Method and apparatus for determining properties of an electrophoretic display
US7002728B2 (en) * 1997-08-28 2006-02-21 E Ink Corporation Electrophoretic particles, and processes for the production thereof
US20060038772A1 (en) * 1995-07-20 2006-02-23 E Ink Corporation Methods for driving electrophoretic displays using dielectrophoretic forces
US7012735B2 (en) * 2003-03-27 2006-03-14 E Ink Corporaiton Electro-optic assemblies, and materials for use therein
US7012600B2 (en) * 1999-04-30 2006-03-14 E Ink Corporation Methods for driving bistable electro-optic displays, and apparatus for use therein
US20070013683A1 (en) * 2003-10-03 2007-01-18 Koninkijkle Phillips Electronics N.V. Electrophoretic display unit
US7167155B1 (en) * 1995-07-20 2007-01-23 E Ink Corporation Color electrophoretic displays
US7170670B2 (en) * 2001-04-02 2007-01-30 E Ink Corporation Electrophoretic medium and display with improved image stability
US7173752B2 (en) * 2003-11-05 2007-02-06 E Ink Corporation Electro-optic displays, and materials for use therein
US7176880B2 (en) * 1999-07-21 2007-02-13 E Ink Corporation Use of a storage capacitor to enhance the performance of an active matrix driven electronic display
US20070035808A1 (en) * 2001-07-09 2007-02-15 E Ink Corporation Electro-optic display and materials for use therein
US7180649B2 (en) * 2001-04-19 2007-02-20 E Ink Corporation Electrochromic-nanoparticle displays
US20070052757A1 (en) * 1996-07-19 2007-03-08 E Ink Corporation Electronically addressable microencapsulated ink and display thereof
US7193625B2 (en) * 1999-04-30 2007-03-20 E Ink Corporation Methods for driving electro-optic displays, and apparatus for use therein
US20070069247A1 (en) * 2002-04-24 2007-03-29 E Ink Corporation Electro-optic displays, and components for use therein
US20080013156A1 (en) * 2006-07-13 2008-01-17 E Ink Corporation Particles for use in electrophoretic displays
US20080013155A1 (en) * 2006-07-11 2008-01-17 E Ink Corporation Electrophoretic medium and display with improved image stability
US7321459B2 (en) * 2002-03-06 2008-01-22 Bridgestone Corporation Image display device and method
US20080023332A1 (en) * 2003-03-25 2008-01-31 E Ink Corporation Processes for the production of electrophoretic displays
US20080024482A1 (en) * 2002-06-13 2008-01-31 E Ink Corporation Methods for driving electro-optic displays
US20080024429A1 (en) * 2006-07-25 2008-01-31 E Ink Corporation Electrophoretic displays using gaseous fluids
US7327511B2 (en) * 2004-03-23 2008-02-05 E Ink Corporation Light modulators
US20080030832A1 (en) * 2006-08-02 2008-02-07 E Ink Corporation Multi-layer light modulator
US20080043318A1 (en) * 2005-10-18 2008-02-21 E Ink Corporation Color electro-optic displays, and processes for the production thereof
US20080048969A1 (en) * 2003-06-30 2008-02-28 E Ink Corporation Methods for driving electrophoretic displays
US7339715B2 (en) * 2003-03-25 2008-03-04 E Ink Corporation Processes for the production of electrophoretic displays
US20080074730A1 (en) * 2006-09-22 2008-03-27 E Ink Corporation Electro-optic display and materials for use therein
US20090004442A1 (en) * 2007-06-28 2009-01-01 E Ink Corporation Processes for the production of electro-optic displays, and color filters for use therein
US20090000729A1 (en) * 2007-06-29 2009-01-01 E Ink Corporation Electro-optic displays, and materials and methods for production thereof
US20090009852A1 (en) * 2001-05-15 2009-01-08 E Ink Corporation Electrophoretic particles and processes for the production thereof
US20090029527A1 (en) * 2002-04-24 2009-01-29 E Ink Corporation Processes for forming backplanes for electro-optic displays
US20090040594A1 (en) * 1995-07-20 2009-02-12 E Ink Corporation Multi-color electrophoretic displays and materials for making the same
US7492339B2 (en) * 2004-03-26 2009-02-17 E Ink Corporation Methods for driving bistable electro-optic displays
US20090046082A1 (en) * 2003-10-08 2009-02-19 E Ink Corporation Electrowetting displays
US7649666B2 (en) * 2006-12-07 2010-01-19 E Ink Corporation Components and methods for use in electro-optic displays
US7649674B2 (en) * 2002-06-10 2010-01-19 E Ink Corporation Electro-optic display with edge seal
US7667684B2 (en) * 1998-07-08 2010-02-23 E Ink Corporation Methods for achieving improved color in microencapsulated electrophoretic devices
US7667886B2 (en) * 2007-01-22 2010-02-23 E Ink Corporation Multi-layer sheet for use in electro-optic displays
US7672040B2 (en) * 2003-11-05 2010-03-02 E Ink Corporation Electro-optic displays, and materials for use therein
US7679599B2 (en) * 2005-03-04 2010-03-16 Seiko Epson Corporation Electrophoretic device, method of driving electrophoretic device, and electronic apparatus
US7679814B2 (en) * 2001-04-02 2010-03-16 E Ink Corporation Materials for use in electrophoretic displays
US7688497B2 (en) * 2007-01-22 2010-03-30 E Ink Corporation Multi-layer sheet for use in electro-optic displays

Family Cites Families (154)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3892568A (en) 1969-04-23 1975-07-01 Matsushita Electric Ind Co Ltd Electrophoretic image reproduction process
US3668106A (en) 1970-04-09 1972-06-06 Matsushita Electric Ind Co Ltd Electrophoretic display device
US3767392A (en) 1970-04-15 1973-10-23 Matsushita Electric Ind Co Ltd Electrophoretic light image reproduction process
JPS4917079B1 (en) 1970-12-21 1974-04-26
US4448493A (en) 1981-02-25 1984-05-15 Toppan Printing Co., Ltd. Electrochromic display device
US4418346A (en) 1981-05-20 1983-11-29 Batchelder J Samuel Method and apparatus for providing a dielectrophoretic display of visual information
US4550982A (en) 1981-11-09 1985-11-05 Nippon Electric Co., Ltd. All-solid-state display including an organic electrochromic layer with ion donor/acceptor
US6137467A (en) 1995-01-03 2000-10-24 Xerox Corporation Optically sensitive electric paper
US5784190A (en) 1995-04-27 1998-07-21 John M. Baker Electro-micro-mechanical shutters on transparent substrates
US8139050B2 (en) 1995-07-20 2012-03-20 E Ink Corporation Addressing schemes for electronic displays
US7109968B2 (en) 1995-07-20 2006-09-19 E Ink Corporation Non-spherical cavity electrophoretic displays and methods and materials for making the same
US6118426A (en) 1995-07-20 2000-09-12 E Ink Corporation Transducers and indicators having printed displays
US7411719B2 (en) 1995-07-20 2008-08-12 E Ink Corporation Electrophoretic medium and process for the production thereof
US7304634B2 (en) 1995-07-20 2007-12-04 E Ink Corporation Rear electrode structures for electrophoretic displays
US7247379B2 (en) 1997-08-28 2007-07-24 E Ink Corporation Electrophoretic particles, and processes for the production thereof
US6727881B1 (en) 1995-07-20 2004-04-27 E Ink Corporation Encapsulated electrophoretic displays and methods and materials for making the same
US6664944B1 (en) 1995-07-20 2003-12-16 E-Ink Corporation Rear electrode structures for electrophoretic displays
US7071913B2 (en) 1995-07-20 2006-07-04 E Ink Corporation Retroreflective electrophoretic displays and materials for making the same
US7848006B2 (en) 1995-07-20 2010-12-07 E Ink Corporation Electrophoretic displays with controlled amounts of pigment
US7256766B2 (en) 1998-08-27 2007-08-14 E Ink Corporation Electrophoretic display comprising optical biasing element
US7583251B2 (en) 1995-07-20 2009-09-01 E Ink Corporation Dielectrophoretic displays
US6639578B1 (en) 1995-07-20 2003-10-28 E Ink Corporation Flexible displays
US7352353B2 (en) 1995-07-20 2008-04-01 E Ink Corporation Electrostatically addressable electrophoretic display
US7106296B1 (en) 1995-07-20 2006-09-12 E Ink Corporation Electronic book with multiple page displays
US6120839A (en) 1995-07-20 2000-09-19 E Ink Corporation Electro-osmotic displays and materials for making the same
US7259744B2 (en) 1995-07-20 2007-08-21 E Ink Corporation Dielectrophoretic displays
US20080136774A1 (en) 2004-07-27 2008-06-12 E Ink Corporation Methods for driving electrophoretic displays using dielectrophoretic forces
US7956841B2 (en) 1995-07-20 2011-06-07 E Ink Corporation Stylus-based addressing structures for displays
US6459418B1 (en) 1995-07-20 2002-10-01 E Ink Corporation Displays combining active and non-active inks
US6262706B1 (en) 1995-07-20 2001-07-17 E Ink Corporation Retroreflective electrophoretic displays and materials for making the same
US5760761A (en) 1995-12-15 1998-06-02 Xerox Corporation Highlight color twisting ball display
US6306509B2 (en) * 1996-03-21 2001-10-23 Showa Denko K.K. Ion conductive laminate and production method and use thereof
US5808783A (en) 1996-06-27 1998-09-15 Xerox Corporation High reflectance gyricon display
US6721083B2 (en) 1996-07-19 2004-04-13 E Ink Corporation Electrophoretic displays using nanoparticles
US6120588A (en) 1996-07-19 2000-09-19 E Ink Corporation Electronically addressable microencapsulated ink and display thereof
US6323989B1 (en) 1996-07-19 2001-11-27 E Ink Corporation Electrophoretic displays using nanoparticles
US5930026A (en) 1996-10-25 1999-07-27 Massachusetts Institute Of Technology Nonemissive displays and piezoelectric power supplies therefor
US5777782A (en) 1996-12-24 1998-07-07 Xerox Corporation Auxiliary optics for a twisting ball display
EP0958526B1 (en) 1997-02-06 2005-06-15 University College Dublin Electrochromic system
US5961804A (en) 1997-03-18 1999-10-05 Massachusetts Institute Of Technology Microencapsulated electrophoretic display
US6980196B1 (en) 1997-03-18 2005-12-27 Massachusetts Institute Of Technology Printable electronic display
US6067185A (en) 1997-08-28 2000-05-23 E Ink Corporation Process for creating an encapsulated electrophoretic display
US8390918B2 (en) 2001-04-02 2013-03-05 E Ink Corporation Electrophoretic displays with controlled amounts of pigment
US7230750B2 (en) 2001-05-15 2007-06-12 E Ink Corporation Electrophoretic media and processes for the production thereof
US6252564B1 (en) 1997-08-28 2001-06-26 E Ink Corporation Tiled displays
US6300932B1 (en) 1997-08-28 2001-10-09 E Ink Corporation Electrophoretic displays with luminescent particles and materials for making the same
US6825829B1 (en) 1997-08-28 2004-11-30 E Ink Corporation Adhesive backed displays
US7242513B2 (en) 1997-08-28 2007-07-10 E Ink Corporation Encapsulated electrophoretic displays having a monolayer of capsules and materials and methods for making the same
DE69917441T2 (en) 1998-03-18 2004-09-23 E-Ink Corp., Cambridge electrophoretic display
US6753999B2 (en) 1998-03-18 2004-06-22 E Ink Corporation Electrophoretic displays in portable devices and systems for addressing such displays
US6498114B1 (en) 1999-04-09 2002-12-24 E Ink Corporation Method for forming a patterned semiconductor film
US6312304B1 (en) 1998-12-15 2001-11-06 E Ink Corporation Assembly of microencapsulated electronic displays
WO1999059101A2 (en) 1998-05-12 1999-11-18 E-Ink Corporation Microencapsulated electrophoretic electrostatically-addressed media for drawing device applications
US6241921B1 (en) 1998-05-15 2001-06-05 Massachusetts Institute Of Technology Heterogeneous display elements and methods for their fabrication
WO1999067678A2 (en) 1998-06-22 1999-12-29 E-Ink Corporation Means of addressing microencapsulated display media
EP1099207B1 (en) 1998-07-22 2002-03-27 E-Ink Corporation Electronic display
US7079305B2 (en) 2001-03-19 2006-07-18 E Ink Corporation Electrophoretic medium and process for the production thereof
US6225971B1 (en) 1998-09-16 2001-05-01 International Business Machines Corporation Reflective electrophoretic display with laterally adjacent color cells using an absorbing panel
US6271823B1 (en) 1998-09-16 2001-08-07 International Business Machines Corporation Reflective electrophoretic display with laterally adjacent color cells using a reflective panel
US6144361A (en) 1998-09-16 2000-11-07 International Business Machines Corporation Transmissive electrophoretic display with vertical electrodes
US6140405A (en) 1998-09-21 2000-10-31 The B. F. Goodrich Company Salt-modified electrostatic dissipative polymers
US6262833B1 (en) 1998-10-07 2001-07-17 E Ink Corporation Capsules for electrophoretic displays and methods for making the same
US6128124A (en) 1998-10-16 2000-10-03 Xerox Corporation Additive color electric paper without registration or alignment of individual elements
US20070285385A1 (en) 1998-11-02 2007-12-13 E Ink Corporation Broadcast system for electronic ink signs
WO2000026761A1 (en) 1998-11-02 2000-05-11 E Ink Corporation Broadcast system for display devices made of electronic ink
US6147791A (en) 1998-11-25 2000-11-14 Xerox Corporation Gyricon displays utilizing rotating elements and magnetic latching
US6097531A (en) 1998-11-25 2000-08-01 Xerox Corporation Method of making uniformly magnetized elements for a gyricon display
EP1141889A1 (en) 1998-12-18 2001-10-10 E Ink Corporation Electronic ink display media for security and authentication
US6724519B1 (en) 1998-12-21 2004-04-20 E-Ink Corporation Protective electrodes for electrophoretic displays
WO2000038000A1 (en) 1998-12-22 2000-06-29 E Ink Corporation Method of manufacturing of a discrete electronic device
WO2000060410A1 (en) 1999-04-06 2000-10-12 E Ink Corporation Microcell electrophoretic displays
US7952557B2 (en) 2001-11-20 2011-05-31 E Ink Corporation Methods and apparatus for driving electro-optic displays
US7119772B2 (en) 1999-04-30 2006-10-10 E Ink Corporation Methods for driving bistable electro-optic displays, and apparatus for use therein
US8125501B2 (en) 2001-11-20 2012-02-28 E Ink Corporation Voltage modulated driver circuits for electro-optic displays
US8289250B2 (en) 2004-03-31 2012-10-16 E Ink Corporation Methods for driving electro-optic displays
US7038655B2 (en) 1999-05-03 2006-05-02 E Ink Corporation Electrophoretic ink composed of particles with field dependent mobilities
US7119759B2 (en) 1999-05-03 2006-10-10 E Ink Corporation Machine-readable displays
US8115729B2 (en) 1999-05-03 2012-02-14 E Ink Corporation Electrophoretic display element with filler particles
WO2000067110A1 (en) 1999-05-03 2000-11-09 E Ink Corporation Display unit for electronic shelf price label system
US8009348B2 (en) 1999-05-03 2011-08-30 E Ink Corporation Machine-readable displays
US7030412B1 (en) 1999-05-05 2006-04-18 E Ink Corporation Minimally-patterned semiconductor devices for display applications
AT502320T (en) 1999-07-01 2011-04-15 E Ink Corp An electrophoretic medium provided with spacers
WO2001017040A1 (en) 1999-08-31 2001-03-08 E Ink Corporation A solvent annealing process for forming a thin semiconductor film with advantageous properties
US6788449B2 (en) 2000-03-03 2004-09-07 Sipix Imaging, Inc. Electrophoretic display and novel process for its manufacture
CN1237623C (en) 2000-04-18 2006-01-18 伊英克公司 Method for forming transistor on the underlay and underlay with polyphenylenes polyimides
US7893435B2 (en) 2000-04-18 2011-02-22 E Ink Corporation Flexible electronic circuits and displays including a backplane comprising a patterned metal foil having a plurality of apertures extending therethrough
US7236290B1 (en) 2000-07-25 2007-06-26 E Ink Corporation Electrophoretic medium with improved stability
US6816147B2 (en) 2000-08-17 2004-11-09 E Ink Corporation Bistable electro-optic display, and method for addressing same
WO2002045061A2 (en) 2000-11-29 2002-06-06 E Ink Corporation Addressing circuitry for large electronic displays
AU3061002A (en) 2000-12-05 2002-06-18 E Ink Corp Displays for portable electronic apparatus
JP4198999B2 (en) 2001-03-13 2008-12-17 イー インク コーポレイション Apparatus for displaying the drawings
EP1393122B1 (en) 2001-05-15 2018-03-28 E Ink Corporation Electrophoretic particles
JP2004535599A (en) 2001-07-09 2004-11-25 イー−インク コーポレイション Electro-optical display and the adhesive composition
AU2002354672A1 (en) 2001-07-09 2003-01-29 E Ink Corporation Electro-optical display having a lamination adhesive layer
US7110163B2 (en) 2001-07-09 2006-09-19 E Ink Corporation Electro-optic display and lamination adhesive for use therein
US6967640B2 (en) 2001-07-27 2005-11-22 E Ink Corporation Microencapsulated electrophoretic display with integrated driver
US6819471B2 (en) 2001-08-16 2004-11-16 E Ink Corporation Light modulation by frustration of total internal reflection
US6825970B2 (en) 2001-09-14 2004-11-30 E Ink Corporation Methods for addressing electro-optic materials
US7453445B2 (en) 2004-08-13 2008-11-18 E Ink Corproation Methods for driving electro-optic displays
US20050259068A1 (en) 2001-12-10 2005-11-24 Norio Nihei Image display
US6900851B2 (en) 2002-02-08 2005-05-31 E Ink Corporation Electro-optic displays and optical systems for addressing such displays
EP1484635A4 (en) 2002-02-15 2008-02-20 Bridgestone Corp Image display unit
US6950220B2 (en) 2002-03-18 2005-09-27 E Ink Corporation Electro-optic displays, and methods for driving same
WO2003088495A1 (en) 2002-04-17 2003-10-23 Bridgestone Corporation Image display unit
EP1497867A2 (en) 2002-04-24 2005-01-19 E Ink Corporation Electronic displays
WO2003091799A1 (en) 2002-04-26 2003-11-06 Bridgestone Corporation Particle for image display and its apparatus
US6958848B2 (en) 2002-05-23 2005-10-25 E Ink Corporation Capsules, materials for use therein and electrophoretic media and displays containing such capsules
US7843621B2 (en) 2002-06-10 2010-11-30 E Ink Corporation Components and testing methods for use in the production of electro-optic displays
US7110164B2 (en) 2002-06-10 2006-09-19 E Ink Corporation Electro-optic displays, and processes for the production thereof
US7583427B2 (en) 2002-06-10 2009-09-01 E Ink Corporation Components and methods for use in electro-optic displays
KR100729970B1 (en) 2002-06-21 2007-06-20 가부시키가이샤 브리지스톤 Image display and method for manufacturing image display
US7202847B2 (en) 2002-06-28 2007-04-10 E Ink Corporation Voltage modulated driver circuits for electro-optic displays
AU2003252656A1 (en) 2002-07-17 2004-02-02 Bridgestone Corporation Image display
US20040105036A1 (en) 2002-08-06 2004-06-03 E Ink Corporation Protection of electro-optic displays against thermal effects
US7312916B2 (en) 2002-08-07 2007-12-25 E Ink Corporation Electrophoretic media containing specularly reflective particles
US7839564B2 (en) 2002-09-03 2010-11-23 E Ink Corporation Components and methods for use in electro-optic displays
WO2004023202A1 (en) 2002-09-03 2004-03-18 E Ink Corporation Electrophoretic medium with gaseous suspending fluid
EP1552337B1 (en) 2002-09-03 2016-04-27 E Ink Corporation Electro-optic displays
TW575646B (en) 2002-09-04 2004-02-11 Sipix Imaging Inc Novel adhesive and sealing layers for electrophoretic displays
US7166182B2 (en) 2002-09-04 2007-01-23 Sipix Imaging, Inc. Adhesive and sealing layers for electrophoretic displays
CN1268656C (en) * 2002-11-15 2006-08-09 中国科学院化学研究所 Preparing method and application for poly p-phenyl vinylene (PPV)
EP1573389B1 (en) 2002-12-16 2018-05-30 E Ink Corporation Backplanes for electro-optic displays
AU2003289411A1 (en) 2002-12-17 2004-07-09 Bridgestone Corporation Image display panel manufacturing method, image display device manufacturing method, and image display device
US6922276B2 (en) 2002-12-23 2005-07-26 E Ink Corporation Flexible electro-optic displays
WO2004059379A1 (en) 2002-12-24 2004-07-15 Bridgestone Corporation Image display
WO2004077140A1 (en) 2003-02-25 2004-09-10 Bridgestone Corporation Image displaying panel and image display unit
WO2004090626A1 (en) 2003-04-02 2004-10-21 Bridgestone Corporation Particle used for image display medium, image display panel using same, and image display
WO2005010598A2 (en) 2003-07-24 2005-02-03 E Ink Corporation Electro-optic displays
WO2005020199A2 (en) 2003-08-19 2005-03-03 E Ink Corporation Methods for controlling electro-optic displays
EP1671304B1 (en) 2003-10-08 2008-08-20 E Ink Corporation Electro-wetting displays
US20050122306A1 (en) 2003-10-29 2005-06-09 E Ink Corporation Electro-optic displays with single edge addressing and removable driver circuitry
US8177942B2 (en) 2003-11-05 2012-05-15 E Ink Corporation Electro-optic displays, and materials for use therein
US7551346B2 (en) 2003-11-05 2009-06-23 E Ink Corporation Electro-optic displays, and materials for use therein
US7342068B2 (en) 2003-11-18 2008-03-11 Air Products And Chemicals, Inc. Aqueous polyurethane dispersion and method for making and using same
US8928562B2 (en) 2003-11-25 2015-01-06 E Ink Corporation Electro-optic displays, and methods for driving same
US20070103427A1 (en) 2003-11-25 2007-05-10 Koninklijke Philips Electronice N.V. Display apparatus with a display device and a cyclic rail-stabilized method of driving the display device
US7206119B2 (en) 2003-12-31 2007-04-17 E Ink Corporation Electro-optic displays, and method for driving same
US7075703B2 (en) 2004-01-16 2006-07-11 E Ink Corporation Process for sealing electro-optic displays
US20050156340A1 (en) 2004-01-20 2005-07-21 E Ink Corporation Preparation of capsules
US7388572B2 (en) 2004-02-27 2008-06-17 E Ink Corporation Backplanes for electro-optic displays
US20080130092A1 (en) 2004-03-23 2008-06-05 E Ink Corporation Light modulators
US20050253777A1 (en) 2004-05-12 2005-11-17 E Ink Corporation Tiled displays and methods for driving same
WO2006015044A1 (en) 2004-07-27 2006-02-09 E Ink Corporation Electro-optic displays
JP2008521065A (en) 2005-01-26 2008-06-19 イー インク コーポレイション Electrophoretic display using gaseous fluid
JP4718859B2 (en) 2005-02-17 2011-07-06 イー インク コーポレイション Electrophoresis apparatus and its driving method, and electronic equipment
WO2007002452A2 (en) 2005-06-23 2007-01-04 E Ink Corporation Edge seals and processes for electro-optic displays
US20070091417A1 (en) 2005-10-25 2007-04-26 E Ink Corporation Electrophoretic media and displays with improved binder
US7843624B2 (en) 2006-03-08 2010-11-30 E Ink Corporation Electro-optic displays, and materials and methods for production thereof
US8390301B2 (en) 2006-03-08 2013-03-05 E Ink Corporation Electro-optic displays, and materials and methods for production thereof
US7733554B2 (en) 2006-03-08 2010-06-08 E Ink Corporation Electro-optic displays, and materials and methods for production thereof
US8610988B2 (en) 2006-03-09 2013-12-17 E Ink Corporation Electro-optic display with edge seal
US7952790B2 (en) 2006-03-22 2011-05-31 E Ink Corporation Electro-optic media produced using ink jet printing
US7826129B2 (en) 2007-03-06 2010-11-02 E Ink Corporation Materials for use in electrophoretic displays
EP2150881A4 (en) 2007-05-21 2010-09-22 E Ink Corp Methods for driving video electro-optic displays

Patent Citations (99)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US719008A (en) * 1902-10-20 1903-01-27 Int Harvester Co Folding frame for grinders.
US3870517A (en) * 1969-10-18 1975-03-11 Matsushita Electric Ind Co Ltd Color image reproduction sheet employed in photoelectrophoretic imaging
US3792308A (en) * 1970-06-08 1974-02-12 Matsushita Electric Ind Co Ltd Electrophoretic display device of the luminescent type
US5891366A (en) * 1994-05-10 1999-04-06 Robert Bosch Gmbh Anisotropically conducting adhesive, and process for producing an anisotropically conducting adhesive
US5745094A (en) * 1994-12-28 1998-04-28 International Business Machines Corporation Electrophoretic display
US5872552A (en) * 1994-12-28 1999-02-16 International Business Machines Corporation Electrophoretic display
US6184331B1 (en) * 1995-05-25 2001-02-06 Mearthane Products Corporation Preparation of conductive polyurethanes using a conductive quasi-solution
US20090040594A1 (en) * 1995-07-20 2009-02-12 E Ink Corporation Multi-color electrophoretic displays and materials for making the same
US6710540B1 (en) * 1995-07-20 2004-03-23 E Ink Corporation Electrostatically-addressable electrophoretic display
US6515649B1 (en) * 1995-07-20 2003-02-04 E Ink Corporation Suspended particle displays and materials for making the same
US20060038772A1 (en) * 1995-07-20 2006-02-23 E Ink Corporation Methods for driving electrophoretic displays using dielectrophoretic forces
US6680725B1 (en) * 1995-07-20 2004-01-20 E Ink Corporation Methods of manufacturing electronically addressable displays
US7167155B1 (en) * 1995-07-20 2007-01-23 E Ink Corporation Color electrophoretic displays
US6017584A (en) * 1995-07-20 2000-01-25 E Ink Corporation Multi-color electrophoretic displays and materials for making the same
US6055091A (en) * 1996-06-27 2000-04-25 Xerox Corporation Twisting-cylinder display
US6538801B2 (en) * 1996-07-19 2003-03-25 E Ink Corporation Electrophoretic displays using nanoparticles
US20070052757A1 (en) * 1996-07-19 2007-03-08 E Ink Corporation Electronically addressable microencapsulated ink and display thereof
US20070057908A1 (en) * 1996-07-19 2007-03-15 E Ink Corporation Electronically addressable microencapsulated ink and display thereof
US6171522B1 (en) * 1996-12-30 2001-01-09 Hydro-Qu{acute over (e)}bec Heterocyclic aromatic anion salts, and their uses as ionic conducting materials
US6839158B2 (en) * 1997-08-28 2005-01-04 E Ink Corporation Encapsulated electrophoretic displays having a monolayer of capsules and materials and methods for making the same
US6842167B2 (en) * 1997-08-28 2005-01-11 E Ink Corporation Rear electrode structures for displays
US6535197B1 (en) * 1997-08-28 2003-03-18 E Ink Corporation Printable electrode structures for displays
US6177921B1 (en) * 1997-08-28 2001-01-23 E Ink Corporation Printable electrode structures for displays
US7002728B2 (en) * 1997-08-28 2006-02-21 E Ink Corporation Electrophoretic particles, and processes for the production thereof
US6054071A (en) * 1998-01-28 2000-04-25 Xerox Corporation Poled electrets for gyricon-based electric-paper displays
US6704133B2 (en) * 1998-03-18 2004-03-09 E-Ink Corporation Electro-optic display overlays and systems for addressing such displays
US20080048970A1 (en) * 1998-04-10 2008-02-28 E Ink Corporation Full color reflective display with multichromatic sub-pixels
US6864875B2 (en) * 1998-04-10 2005-03-08 E Ink Corporation Full color reflective display with multichromatic sub-pixels
US6518949B2 (en) * 1998-04-10 2003-02-11 E Ink Corporation Electronic displays using organic-based field effect transistors
US6172798B1 (en) * 1998-04-27 2001-01-09 E Ink Corporation Shutter mode microencapsulated electrophoretic display
US6995550B2 (en) * 1998-07-08 2006-02-07 E Ink Corporation Method and apparatus for determining properties of an electrophoretic display
US6512354B2 (en) * 1998-07-08 2003-01-28 E Ink Corporation Method and apparatus for sensing the state of an electrophoretic display
US7667684B2 (en) * 1998-07-08 2010-02-23 E Ink Corporation Methods for achieving improved color in microencapsulated electrophoretic devices
USD485294S1 (en) * 1998-07-22 2004-01-13 E Ink Corporation Electrode structure for an electronic display
US6866760B2 (en) * 1998-08-27 2005-03-15 E Ink Corporation Electrophoretic medium and process for the production thereof
US6184856B1 (en) * 1998-09-16 2001-02-06 International Business Machines Corporation Transmissive electrophoretic display with laterally adjacent color cells
US6376828B1 (en) * 1998-10-07 2002-04-23 E Ink Corporation Illumination system for nonemissive electronic displays
US6506438B2 (en) * 1998-12-15 2003-01-14 E Ink Corporation Method for printing of transistor arrays on plastic substrates
US6377387B1 (en) * 1999-04-06 2002-04-23 E Ink Corporation Methods for producing droplets for use in capsule-based electrophoretic displays
US6842657B1 (en) * 1999-04-09 2005-01-11 E Ink Corporation Reactive formation of dielectric layers and protection of organic layers in organic semiconductor device fabrication
US6531997B1 (en) * 1999-04-30 2003-03-11 E Ink Corporation Methods for addressing electrophoretic displays
US7193625B2 (en) * 1999-04-30 2007-03-20 E Ink Corporation Methods for driving electro-optic displays, and apparatus for use therein
US7688297B2 (en) * 1999-04-30 2010-03-30 E Ink Corporation Methods for driving bistable electro-optic displays, and apparatus for use therein
US7012600B2 (en) * 1999-04-30 2006-03-14 E Ink Corporation Methods for driving bistable electro-optic displays, and apparatus for use therein
US6693620B1 (en) * 1999-05-03 2004-02-17 E Ink Corporation Threshold addressing of electrophoretic displays
US7176880B2 (en) * 1999-07-21 2007-02-13 E Ink Corporation Use of a storage capacitor to enhance the performance of an active matrix driven electronic display
US6521489B2 (en) * 1999-07-21 2003-02-18 E Ink Corporation Preferred methods for producing electrical circuit elements used to control an electronic display
US6545291B1 (en) * 1999-08-31 2003-04-08 E Ink Corporation Transistor design for use in the construction of an electronically driven display
US6870657B1 (en) * 1999-10-11 2005-03-22 University College Dublin Electrochromic device
US6672921B1 (en) * 2000-03-03 2004-01-06 Sipix Imaging, Inc. Manufacturing process for electrophoretic display
US6504524B1 (en) * 2000-03-08 2003-01-07 E Ink Corporation Addressing methods for displays having zero time-average field
US6683333B2 (en) * 2000-07-14 2004-01-27 E Ink Corporation Fabrication of electronic circuit elements using unpatterned semiconductor layers
US20020027635A1 (en) * 2000-09-05 2002-03-07 Fuji Xerox Co., Ltd Display device
US7679814B2 (en) * 2001-04-02 2010-03-16 E Ink Corporation Materials for use in electrophoretic displays
US7170670B2 (en) * 2001-04-02 2007-01-30 E Ink Corporation Electrophoretic medium and display with improved image stability
US7180649B2 (en) * 2001-04-19 2007-02-20 E Ink Corporation Electrochromic-nanoparticle displays
US6870661B2 (en) * 2001-05-15 2005-03-22 E Ink Corporation Electrophoretic displays containing magnetic particles
US20090009852A1 (en) * 2001-05-15 2009-01-08 E Ink Corporation Electrophoretic particles and processes for the production thereof
US20070035808A1 (en) * 2001-07-09 2007-02-15 E Ink Corporation Electro-optic display and materials for use therein
US20050024353A1 (en) * 2001-11-20 2005-02-03 E Ink Corporation Methods for driving electro-optic displays
US6865010B2 (en) * 2001-12-13 2005-03-08 E Ink Corporation Electrophoretic electronic displays with low-index films
US20060017069A1 (en) * 2002-02-18 2006-01-26 Robert Bergmann Electronic component with an adhesive layer and method for the production thereof
US7321459B2 (en) * 2002-03-06 2008-01-22 Bridgestone Corporation Image display device and method
US20070069247A1 (en) * 2002-04-24 2007-03-29 E Ink Corporation Electro-optic displays, and components for use therein
US20090029527A1 (en) * 2002-04-24 2009-01-29 E Ink Corporation Processes for forming backplanes for electro-optic displays
US7649674B2 (en) * 2002-06-10 2010-01-19 E Ink Corporation Electro-optic display with edge seal
US20090034057A1 (en) * 2002-06-10 2009-02-05 E Ink Corporation Components and methods for use in electro-optic displays
US20080054879A1 (en) * 2002-06-10 2008-03-06 E Ink Corporation Components and methods for use in electro-optic displays
US6982178B2 (en) * 2002-06-10 2006-01-03 E Ink Corporation Components and methods for use in electro-optic displays
US20080024482A1 (en) * 2002-06-13 2008-01-31 E Ink Corporation Methods for driving electro-optic displays
US6842279B2 (en) * 2002-06-27 2005-01-11 E Ink Corporation Illumination system for nonemissive electronic displays
US20040060635A1 (en) * 2002-09-25 2004-04-01 Heinrich Diepers Method of producing an adhesive bond
US6987603B2 (en) * 2003-01-31 2006-01-17 E Ink Corporation Construction of electrophoretic displays
US7339715B2 (en) * 2003-03-25 2008-03-04 E Ink Corporation Processes for the production of electrophoretic displays
US20080023332A1 (en) * 2003-03-25 2008-01-31 E Ink Corporation Processes for the production of electrophoretic displays
US7012735B2 (en) * 2003-03-27 2006-03-14 E Ink Corporaiton Electro-optic assemblies, and materials for use therein
US20050012980A1 (en) * 2003-05-02 2005-01-20 E Ink Corporation Electrophoretic displays with controlled amounts of pigment
US20080048969A1 (en) * 2003-06-30 2008-02-28 E Ink Corporation Methods for driving electrophoretic displays
US20050062714A1 (en) * 2003-09-19 2005-03-24 E Ink Corporation Methods for reducing edge effects in electro-optic displays
US20070013683A1 (en) * 2003-10-03 2007-01-18 Koninkijkle Phillips Electronics N.V. Electrophoretic display unit
US20090046082A1 (en) * 2003-10-08 2009-02-19 E Ink Corporation Electrowetting displays
US7349148B2 (en) * 2003-11-05 2008-03-25 E Ink Corporation Electro-optic displays, and materials for use therein
US7173752B2 (en) * 2003-11-05 2007-02-06 E Ink Corporation Electro-optic displays, and materials for use therein
US7672040B2 (en) * 2003-11-05 2010-03-02 E Ink Corporation Electro-optic displays, and materials for use therein
US7327511B2 (en) * 2004-03-23 2008-02-05 E Ink Corporation Light modulators
US7492339B2 (en) * 2004-03-26 2009-02-17 E Ink Corporation Methods for driving bistable electro-optic displays
US7679599B2 (en) * 2005-03-04 2010-03-16 Seiko Epson Corporation Electrophoretic device, method of driving electrophoretic device, and electronic apparatus
US20080043318A1 (en) * 2005-10-18 2008-02-21 E Ink Corporation Color electro-optic displays, and processes for the production thereof
US20080013155A1 (en) * 2006-07-11 2008-01-17 E Ink Corporation Electrophoretic medium and display with improved image stability
US20080013156A1 (en) * 2006-07-13 2008-01-17 E Ink Corporation Particles for use in electrophoretic displays
US20080024429A1 (en) * 2006-07-25 2008-01-31 E Ink Corporation Electrophoretic displays using gaseous fluids
US20080030832A1 (en) * 2006-08-02 2008-02-07 E Ink Corporation Multi-layer light modulator
US7492497B2 (en) * 2006-08-02 2009-02-17 E Ink Corporation Multi-layer light modulator
US20080074730A1 (en) * 2006-09-22 2008-03-27 E Ink Corporation Electro-optic display and materials for use therein
US7649666B2 (en) * 2006-12-07 2010-01-19 E Ink Corporation Components and methods for use in electro-optic displays
US7688497B2 (en) * 2007-01-22 2010-03-30 E Ink Corporation Multi-layer sheet for use in electro-optic displays
US7667886B2 (en) * 2007-01-22 2010-02-23 E Ink Corporation Multi-layer sheet for use in electro-optic displays
US20090004442A1 (en) * 2007-06-28 2009-01-01 E Ink Corporation Processes for the production of electro-optic displays, and color filters for use therein
US20090000729A1 (en) * 2007-06-29 2009-01-01 E Ink Corporation Electro-optic displays, and materials and methods for production thereof

Cited By (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7999787B2 (en) 1995-07-20 2011-08-16 E Ink Corporation Methods for driving electrophoretic displays using dielectrophoretic forces
US8441714B2 (en) 1997-08-28 2013-05-14 E Ink Corporation Multi-color electrophoretic displays
US8040594B2 (en) 1997-08-28 2011-10-18 E Ink Corporation Multi-color electrophoretic displays
US9268191B2 (en) 1997-08-28 2016-02-23 E Ink Corporation Multi-color electrophoretic displays
US9293511B2 (en) 1998-07-08 2016-03-22 E Ink Corporation Methods for achieving improved color in microencapsulated electrophoretic devices
US8553012B2 (en) 2001-03-13 2013-10-08 E Ink Corporation Apparatus for displaying drawings
US7679814B2 (en) 2001-04-02 2010-03-16 E Ink Corporation Materials for use in electrophoretic displays
US8390918B2 (en) 2001-04-02 2013-03-05 E Ink Corporation Electrophoretic displays with controlled amounts of pigment
US8389381B2 (en) 2002-04-24 2013-03-05 E Ink Corporation Processes for forming backplanes for electro-optic displays
US8363299B2 (en) 2002-06-10 2013-01-29 E Ink Corporation Electro-optic displays, and processes for the production thereof
US8322045B2 (en) * 2002-06-13 2012-12-04 Applied Materials, Inc. Single wafer apparatus for drying semiconductor substrates using an inert gas air-knife
US9075280B2 (en) 2002-09-03 2015-07-07 E Ink Corporation Components and methods for use in electro-optic displays
US9740076B2 (en) 2003-12-05 2017-08-22 E Ink Corporation Multi-color electrophoretic displays
US9829764B2 (en) 2003-12-05 2017-11-28 E Ink Corporation Multi-color electrophoretic displays
US8054526B2 (en) 2008-03-21 2011-11-08 E Ink Corporation Electro-optic displays, and color filters for use therein
US8314784B2 (en) 2008-04-11 2012-11-20 E Ink Corporation Methods for driving electro-optic displays
US8270064B2 (en) 2009-02-09 2012-09-18 E Ink Corporation Electrophoretic particles, and processes for the production thereof
US8098418B2 (en) 2009-03-03 2012-01-17 E. Ink Corporation Electro-optic displays, and color filters for use therein
US8441716B2 (en) 2009-03-03 2013-05-14 E Ink Corporation Electro-optic displays, and color filters for use therein
US8754859B2 (en) 2009-10-28 2014-06-17 E Ink Corporation Electro-optic displays with touch sensors and/or tactile feedback
US9778500B2 (en) 2009-10-28 2017-10-03 E Ink Corporation Electro-optic displays with touch sensors and/or tactile feedback
US8654436B1 (en) 2009-10-30 2014-02-18 E Ink Corporation Particles for use in electrophoretic displays
US8446664B2 (en) * 2010-04-02 2013-05-21 E Ink Corporation Electrophoretic media, and materials for use therein
CN102918455A (en) * 2010-04-02 2013-02-06 伊英克公司 Electrophoretic media
US20110286080A1 (en) * 2010-04-02 2011-11-24 E Ink Corporation Electrophoretic media, and materials for use therein
US10190743B2 (en) 2012-04-20 2019-01-29 E Ink Corporation Illumination systems for reflective displays
US9122143B2 (en) 2012-06-07 2015-09-01 Mindflow Llc Dynamically variable graphic material using electrostatically attracted particles
US9715155B1 (en) 2013-01-10 2017-07-25 E Ink Corporation Electrode structures for electro-optic displays
US9726957B2 (en) 2013-01-10 2017-08-08 E Ink Corporation Electro-optic display with controlled electrochemical reactions
US9529240B2 (en) 2014-01-17 2016-12-27 E Ink Corporation Controlled polymeric material conductivity for use in a two-phase electrode layer
US10151955B2 (en) 2014-01-17 2018-12-11 E Ink Corporation Controlled polymeric material conductivity for use in a two-phase electrode layer
US9465206B1 (en) * 2014-02-04 2016-10-11 Amazon Technologies, Inc. Adhesive/sealing material for an electrowetting device
US9671635B2 (en) 2014-02-07 2017-06-06 E Ink Corporation Electro-optic display backplane structures with drive components and pixel electrodes on opposed surfaces
US9506243B1 (en) 2014-03-20 2016-11-29 E Ink Corporation Thermally-responsive film
KR101824723B1 (en) * 2014-09-10 2018-02-02 이 잉크 코포레이션 Colored electrophoretic displays
US20160085132A1 (en) * 2014-09-10 2016-03-24 E Ink Corporation Colored electrophoretic displays
US9921451B2 (en) * 2014-09-10 2018-03-20 E Ink Corporation Colored electrophoretic displays
US10175550B2 (en) 2014-11-07 2019-01-08 E Ink Corporation Applications of electro-optic displays
US9835925B1 (en) 2015-01-08 2017-12-05 E Ink Corporation Electro-optic displays, and processes for the production thereof
WO2016191673A1 (en) 2015-05-27 2016-12-01 E Ink Corporation Methods and circuitry for driving display devices
US10254621B2 (en) 2017-11-03 2019-04-09 E Ink Corporation Electro-optic displays, and processes for the production thereof

Also Published As

Publication number Publication date
JP2014006541A (en) 2014-01-16
CN101855083B (en) 2015-01-21
TW200932517A (en) 2009-08-01
JP2011505586A (en) 2011-02-24
US20160170282A1 (en) 2016-06-16
KR101380453B1 (en) 2014-04-01
JP6147723B2 (en) 2017-06-14
US20160377952A1 (en) 2016-12-29
KR101379587B1 (en) 2014-03-31
KR20140035510A (en) 2014-03-21
JP5696188B2 (en) 2015-04-08
KR20100074275A (en) 2010-07-01
JP2016153923A (en) 2016-08-25
JP2015062083A (en) 2015-04-02
CN101855083A (en) 2010-10-06
TWI451966B (en) 2014-09-11
US10036930B2 (en) 2018-07-31
HK1145478A1 (en) 2015-09-11
EP2217440A4 (en) 2014-08-06
JP5679816B2 (en) 2015-03-04
EP2217440B1 (en) 2019-03-06
WO2009064642A1 (en) 2009-05-22
KR20120089372A (en) 2012-08-09
KR20160106208A (en) 2016-09-09
KR20120135326A (en) 2012-12-12
US9964831B2 (en) 2018-05-08
EP2217440A1 (en) 2010-08-18

Similar Documents

Publication Publication Date Title
US7352353B2 (en) Electrostatically addressable electrophoretic display
CN102967980B (en) A method for manufacturing an electro-optical display
US6788360B2 (en) Stacked liquid cell with liquid-polymer stratified phase separated composite
US6232950B1 (en) Rear electrode structures for displays
US7304634B2 (en) Rear electrode structures for electrophoretic displays
US9164207B2 (en) Electro-optic media produced using ink jet printing
EP1719108B1 (en) Electro-optic display with electro-optic layer adhered to the backplane
US6992808B2 (en) Electrochromic display device and electrodeposition-type display device
US6831770B2 (en) Electrophoretic display and novel process for its manufacture
US8384658B2 (en) Electrostatically addressable electrophoretic display
US6535197B1 (en) Printable electrode structures for displays
US8728266B2 (en) Electro-optic displays, and materials and methods for production thereof
JP5316100B2 (en) Display particle dispersion, a display medium, and a display device
US7038655B2 (en) Electrophoretic ink composed of particles with field dependent mobilities
US6710540B1 (en) Electrostatically-addressable electrophoretic display
US3941901A (en) Surface alignment method for liquid crystal cells and production of polarizers therefor
US7112114B2 (en) Electrophoretic display and process for its manufacture
US7513813B2 (en) Sub-assemblies and processes for the production of electro-optic displays
US9030724B2 (en) Flexible and printable electrooptic devices
US20030021005A1 (en) Electrophoretic display with color filters
US6833943B2 (en) Electrophoretic display and novel process for its manufacture
Liang et al. Microcup® displays: Electronic paper by roll‐to‐roll manufacturing processes
US6664944B1 (en) Rear electrode structures for electrophoretic displays
US7256766B2 (en) Electrophoretic display comprising optical biasing element
US9170467B2 (en) Color electro-optic displays, and processes for the production thereof

Legal Events

Date Code Title Description
AS Assignment

Owner name: E INK CORPORATION, MASSACHUSETTS

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WHITESIDES, THOMAS H.;CAO, LAN;REEL/FRAME:022065/0044;SIGNING DATES FROM 20081105 TO 20081218