EP1513902A1 - Material for the production of a conductive organic functional layer and use thereof - Google Patents

Material for the production of a conductive organic functional layer and use thereof

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Publication number
EP1513902A1
EP1513902A1 EP03759849A EP03759849A EP1513902A1 EP 1513902 A1 EP1513902 A1 EP 1513902A1 EP 03759849 A EP03759849 A EP 03759849A EP 03759849 A EP03759849 A EP 03759849A EP 1513902 A1 EP1513902 A1 EP 1513902A1
Authority
EP
European Patent Office
Prior art keywords
solvent
printing
pedot
mixtures
functional layer
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.)
Withdrawn
Application number
EP03759849A
Other languages
German (de)
French (fr)
Inventor
Christoph Brabec
Karsten Heuser
Henning Rost
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.)
Siemens AG
Original Assignee
Siemens AG
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
Application filed by Siemens AG filed Critical Siemens AG
Publication of EP1513902A1 publication Critical patent/EP1513902A1/en
Withdrawn legal-status Critical Current

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Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes

Definitions

  • the invention relates to a material for a conductive organic functional layer, in particular one based on PEDOT-PSS [poly (3, 4-ethylenedioxythiophene) -poly (styrene-sulfonate)].
  • PEDOT-PSS poly (3, 4-ethylenedioxythiophene) -poly (styrene-sulfonate)
  • PEDOT-PSS with various solvents, including glycol are known, for example from DE 197 57 542.
  • a disadvantage of these materials containing PEDOT-PSS is that the conductivity has been modified by adding solvent additives or other additives. This results in adverse effects on the printability of the polymer layers, with the conductivity still not being optimized.
  • a highly conductive functional polymer is required for organic solar cells, detectors or transistors as well as for organic light-emitting diodes on flexible substrates.
  • this polymer serves as an anode.
  • this PEDOT can be used as a material for the source-drain electrodes.
  • ITO indium tin oxide
  • flexible plastic substrates can be used.
  • the conductive properties of the polymer used for this should come very close to that of the ITO in order to achieve the same performance properties of the components.
  • ITO has a conductivity in the range of 10 4 S / cm and achieves a surface resistance of 20 Ohm / square with a layer thickness of 120 nm.
  • Commercially available PEDOT currently reaches 8 from Bayer or now HC Starck) up to 10 S / cm and from Agfa (Orgacon Folie) 120 S / cm.
  • the PEDOT / PSS dispersions used are currently water-based.
  • the object of the present invention is therefore to provide a material which has an optimized conductivity based on PEDOT-PSS.
  • the invention relates to a material for producing an organic functional layer based on PEDOT-PSS, in which the conductivity is optimized by replacing the solvent, that is to say substituting the first solvent with a second solvent.
  • water or another strongly polar solvent is used as the "first solvent" to be replaced.
  • the “first solvent *” is the solvent in which the functional polymer, PEDOT-PSS, is produced. Accordingly, the “second solvent” is the solvent that is ultimately present in the material in which the functional polymer shows the optimized conductivity.
  • a glycol-containing compound such as ethylene glycol or another alcohol is used as the second solvent, in particular also mixtures of several alcohols and / or alcohols with a carbon content of C4 to C10, branched and unbranched, including polyvalent ones Alcohols, or mixtures thereof, and mixtures with water, particularly preferably glycol and glycerol.
  • organic material or “functional material” or * functional polymer ”here encompasses all types of organic, organometallic and / or organic-inorganic plastics (hybrids), in particular those which are referred to in English, for example, as“ plastics ” all types of substances with the exception of the semiconductors that form the classic diodes (germanium, silicon) and the typical metallic conductors. Accordingly, a restriction in the dogmatic sense to organic material as carbon-containing material is not intended, but rather is The term is not intended to be subject to any restriction with regard to the molecular size, in particular to polymeric and / or oligomeric materials, but the use of "small molecules” is also entirely possible. polymer "in the functional polymer is due to historical reasons and therefore contains no information about the previous are an actually polymeric compound and no statement as to whether it is a polymer mixture or a copolymer or not.
  • the main advantage of the conductive polymer (PEDOT) in ethylene glycol described here is that replacing the water with ethylene glycol significantly increases the conductivity. The reason for this increase has not yet been clarified. On the one hand it can lead to the formation of agglomerates during the replacement of the solvent, on the other hand the addition of ethylene glycol to the PEDOT / PSS chains can lead to improved electricity transport through the formation of hydrogen bonds.
  • PEDOT conductive polymer
  • PEDOT is used as an anode (replacement for ITO) in the field of OLEDs and solar cells on flexible Substrates used.
  • the anode can be applied in a structured manner using an existing printing process, the required conductivity being as close as possible to that of the ITO.
  • the new material can be used very well:
  • PEDOT In the area of organic transistors, highly conductive PEDOT is required in order to implement electrical leads or the source drain electrodes on a polymer basis. - In the field of organic solar cells or detectors, PEDOT is used as an electrode, supply line and as a recombination layer for tandem cells. - In the field of electronic components in general for diodes, resistors for IC + boards
  • Highly conductive PEDOT can also be used for both electrodes in a sandwich device (also for inverted construction).

Abstract

The invention relates to a material for a conductive organic functional layer, particularly one based on PEDOT-PSS [poly(3,4-ethylenedioxythiophene)-poly(styrene sulfonate)]. Conductivity is significantly increased by replacing the solvent.

Description

Beschreibungdescription
Material zur Herstellung einer leitfähigen organischen Funk¬ tionsschicht und Verwendung dazuMaterial for making a conductive organic radio ¬ tion layer and to use
Die Erfindung betrifft ein Material für eine leitfähige organische Funktionsschicht, insbesondere eine auf der Basis von PEDOT-PSS [Poly (3, 4-ethylenedioxythiophene) -poly (styrene- sulfonate) ] .The invention relates to a material for a conductive organic functional layer, in particular one based on PEDOT-PSS [poly (3, 4-ethylenedioxythiophene) -poly (styrene-sulfonate)].
Bekannt sind Lösungen PEDOT-PSS mit verschiedenen, auch Gly- kol enthaltenden, Lösungsmitteln, beispielsweise aus der DE 197 57 542. Nachteilig an diesen PEDOT-PSS enthaltenden Materialien ist, dass die Leitfähigkeit durch Zugabe von Lösungs- mittelzusätzen oder weiteren Zusätzen modifiziert wurde. Dadurch ergeben sich nachteilige Effekte auf die Druckbarkeit der Polymerschichten, wobei die Leitfähigkeit immer noch nicht optimiert ist.Solutions PEDOT-PSS with various solvents, including glycol, are known, for example from DE 197 57 542. A disadvantage of these materials containing PEDOT-PSS is that the conductivity has been modified by adding solvent additives or other additives. This results in adverse effects on the printability of the polymer layers, with the conductivity still not being optimized.
Sowohl für organische Solarzellen, Detektoren, oder Transistoren sowie für organische Leuchtdioden auf flexiblen Substraten wird ein hochleitfähiges Funktionspolymer benötigt. Im Falle der OLEDs und der Solarzellen dient dieses Polymer als Anode. Bei der Verwendung in organischen Feldeffekt- Transistoren kann dieses PEDOT als Material für die Source- Drain Elektroden eingesetzt werden Derzeit wird ITO (Indium- tin-oxide) als ein Anodenmaterial eingesetzt, was durch fehlende Flexibilität (Biegsamkeit ist durch keramische Struktur begrenzt) nicht auf flexiblen Kunststoffsubstraten eingesetzt werden kann. Die leitfähigen Eigenschaften des dafür verwendeten Polymers (z.B. PEDOT) sollen denen des ITO sehr nahe kommen, um gleiche Performance Eigenschaften der Bauelemente zu erzielen.A highly conductive functional polymer is required for organic solar cells, detectors or transistors as well as for organic light-emitting diodes on flexible substrates. In the case of OLEDs and solar cells, this polymer serves as an anode. When used in organic field effect transistors, this PEDOT can be used as a material for the source-drain electrodes. ITO (indium tin oxide) is currently used as an anode material, which is not limited by the lack of flexibility (flexibility is limited by the ceramic structure) flexible plastic substrates can be used. The conductive properties of the polymer used for this (e.g. PEDOT) should come very close to that of the ITO in order to achieve the same performance properties of the components.
ITO hat eine Leitfähigkeit im Bereich von 104 S/cm und erreicht mit einer Schichtdicke von 120 nm einen Oberflächenwiderstand von 20 Ohm/square. Kommerziell erhältliches PEDOT erreicht derzeit 8 von der Firma Bayer bzw. nun HC Starck) bis zu 10 S/cm und von der Firma Agfa (Orgacon Folie) 120 S/cm. Die verwendeten Dispersionen aus PEDOT/PSS sind derzeit wasserbasierend.ITO has a conductivity in the range of 10 4 S / cm and achieves a surface resistance of 20 Ohm / square with a layer thickness of 120 nm. Commercially available PEDOT currently reaches 8 from Bayer or now HC Starck) up to 10 S / cm and from Agfa (Orgacon Folie) 120 S / cm. The PEDOT / PSS dispersions used are currently water-based.
Aufgabe der vorliegenden Erfindung ist es daher, ein Material zur Verfügung zu stellen, das auf der Basis von PEDOT-PSS eine optimierte Leitfähigkeit hat.The object of the present invention is therefore to provide a material which has an optimized conductivity based on PEDOT-PSS.
Allgemeine Erkenntnis der Erfindung ist es, dass ein Ersatz des Lösungsmittels eine gesteigerte Leitfähigkeit des Materials bewirkt, ohne die Verarbeitbarkeit, insbesondere die Druckbarkeit des Materials zu verschlechtern.General knowledge of the invention is that a replacement of the solvent brings about an increased conductivity of the material without impairing the processability, in particular the printability, of the material.
Gegenstand der Erfindung ist ein Material zur Herstellung einer organischen Funktionsschicht auf der Basis von PEDOT-PSS, bei dem die Leitfähigkeit durch Ersatz des Lösungsmittels, also Substitution des ersten Lösungsmittels durch ein zweites Lösungsmittel, optimiert ist.The invention relates to a material for producing an organic functional layer based on PEDOT-PSS, in which the conductivity is optimized by replacing the solvent, that is to say substituting the first solvent with a second solvent.
Nach einer Ausführungsform wird als zu ersetzendes „erstes Lösungsmittel'" Wasser oder ein sonstiges stark polares Lösungsmittel verwendet.According to one embodiment, water or another strongly polar solvent is used as the "first solvent" to be replaced.
Als „erstes Lösungsmittel* wird das Lösungsmittel bezeichnet, in dem das Funktionspolymer, PEDOT-PSS, hergestellt wird. Als „zweites Lösungsmittel wird dementsprechend dann das Lösungsmittel bezeichnet, das letztendlich im Material vorliegt, in dem das Funktionspolymer die optimierte Leitfähig- keit zeigt.The “first solvent *” is the solvent in which the functional polymer, PEDOT-PSS, is produced. Accordingly, the “second solvent” is the solvent that is ultimately present in the material in which the functional polymer shows the optimized conductivity.
Nach einer Ausführungsform wird als zweites Lösungsmittel eine glykolhaltige Verbindung wie Ethylenglykol oder ein sonstiger Alkohol eingesetzt, insbesondere auch Mischungen mehre- rer Alkohole, und/oder Alkohole mit einem Kohlenstoffgehalt von C4 bis C10, verzweigt und unverzweigt, auch mehrwertige Alkohole, bzw. Gemische daraus, sowie Gemische mit Wasser, besonders bevorzugt Glycol und Glycerol.According to one embodiment, a glycol-containing compound such as ethylene glycol or another alcohol is used as the second solvent, in particular also mixtures of several alcohols and / or alcohols with a carbon content of C4 to C10, branched and unbranched, including polyvalent ones Alcohols, or mixtures thereof, and mixtures with water, particularly preferably glycol and glycerol.
Der Begriff "organisches Material" oder "Funktionsmaterial" oder * Funktionspolymer" umfasst hier alle Arten von organischen, metallorganischen und/oder organisch-anorganischen Kunststoffen (Hybride) , insbesondere die, die im Englischen z.B. mit "plastics" bezeichnet werden. Es handelt sich um alle Arten von Stoffen mit Ausnahme der Halbleiter, die die klassischen Dioden bilden (Germanium, Silizium) , und der typischen metallischen Leiter. Eine Beschränkung im dogmatischen Sinn auf organisches Material als Kohlenstoff-enthal- tendes Material ist demnach nicht vorgesehen, vielmehr ist auch an den breiten Einsatz von z.B. Siliconen gedacht. Wei- terhin soll der Term keiner Beschränkung im Hinblick auf die Molekülgröße, insbesondere auf polymere und/oder oligomere Materialien unterliegen, sondern es ist durchaus auch der Einsatz von "small molecules" möglich. Der Wortbestandteil "polymer" im Funktionspolymer ist historisch bedingt und ent- hält insofern keine Aussage über das Vorliegen einer tatsächlich polymeren Verbindung und keine Aussage darüber, ob es sich um ein Polymergemisch oder ein Copolymer handelt oder nicht.The term “organic material” or “functional material” or * functional polymer ”here encompasses all types of organic, organometallic and / or organic-inorganic plastics (hybrids), in particular those which are referred to in English, for example, as“ plastics ” all types of substances with the exception of the semiconductors that form the classic diodes (germanium, silicon) and the typical metallic conductors. Accordingly, a restriction in the dogmatic sense to organic material as carbon-containing material is not intended, but rather is The term is not intended to be subject to any restriction with regard to the molecular size, in particular to polymeric and / or oligomeric materials, but the use of "small molecules" is also entirely possible. polymer "in the functional polymer is due to historical reasons and therefore contains no information about the previous are an actually polymeric compound and no statement as to whether it is a polymer mixture or a copolymer or not.
Der Hauptvorteil des hier beschriebenen leitfähigen Polymers (PEDOT) in Ethylenglykol ist, dass durch das Ersetzen des Wassers durch Ethylenglykol die Leitfähigkeit signifikant erhöht wird. Die Ursache für diese Erhöhung ist derzeit noch nicht geklärt. Zum einen kann es zur Bildung von Agglomeraten bei der Ersetzung des Lösungsmittels führen, andererseits kann die Anlagerung von Ethylenglykol an die PEDOT/PSS Ketten durch Bildung von Wasserstoffbrückenbindungen zu verbessertem Stromtransport führen.The main advantage of the conductive polymer (PEDOT) in ethylene glycol described here is that replacing the water with ethylene glycol significantly increases the conductivity. The reason for this increase has not yet been clarified. On the one hand it can lead to the formation of agglomerates during the replacement of the solvent, on the other hand the addition of ethylene glycol to the PEDOT / PSS chains can lead to improved electricity transport through the formation of hydrogen bonds.
Es gibt zahlreiche Anwendungen für PEDOT im Gebiet der Polymerelektronik. Beispielsweise wird PEDOT als Anode (Ersatz für ITO) im Bereich der OLEDs und Solarzellen auf flexiblen Substraten eingesetzt. In diesem Fall kann die Anode mit einem existierenden Druckprozess direkt strukturiert aufgebracht werden, wobei die geforderte Leitfähigkeit der des ITO möglichst nahe kommt.There are numerous applications for PEDOT in the field of polymer electronics. For example, PEDOT is used as an anode (replacement for ITO) in the field of OLEDs and solar cells on flexible Substrates used. In this case, the anode can be applied in a structured manner using an existing printing process, the required conductivity being as close as possible to that of the ITO.
Überraschend ist, dass durch Ersatz des Lösungsmittels, (z.B. Wasser durch Ethylenglykol) die Leitfähigkeit um zwei Größenordnungen ansteigt.It is surprising that replacing the solvent (e.g. water with ethylene glycol) increases the conductivity by two orders of magnitude.
Das neue Material kann ganz herausragend eingesetzt werden:The new material can be used very well:
Im Bereich der organischen Solarzellen und Transistoren: dort werden ganz spezielle Anforderungen an die Leitfähigkeit der PEDOT Schichten gestellt, die mittels dieser Er- findung auch für die verschiedenen Druckprozesse erfüllt werden können.In the field of organic solar cells and transistors: there are very special requirements for the conductivity of the PEDOT layers, which can also be met for the various printing processes by means of this invention.
Im Bereich der organischen Transistoren wird hochleitfähi- ges PEDOT benötigt, um elektrische Zuleitungen bzw. die Source drain Elektroden auf Polymerbasis zu realisieren. - Im Bereich der organischen Solarzellen oder Detektoren wird PEDOT als Elektrode, Zuleitung und als Rekombinationsschicht für Tandemzellen eingesetzt. - Im Bereich der elektronischen Bauteile allgemein für Dioden, Widerstände für IC+BoardsIn the area of organic transistors, highly conductive PEDOT is required in order to implement electrical leads or the source drain electrodes on a polymer basis. - In the field of organic solar cells or detectors, PEDOT is used as an electrode, supply line and as a recombination layer for tandem cells. - In the field of electronic components in general for diodes, resistors for IC + boards
Hochleitfähiges PEDOT kann auch für beide Elektroden bei einer Sandwich-device (auch für invertierten Aufbau) hergenommen werden. Highly conductive PEDOT can also be used for both electrodes in a sandwich device (also for inverted construction).

Claims

Patentansprüche claims
1. Material zur Herstellung einer leitfähigen organischen Funktionsschicht auf der Basis von PEDOT-PSS, bei dem die Leitfähigkeit durch Ersatz des Lösungsmittels, also durch Substitution eines ersten Lösungsmittels durch ein zweites Lösungsmittel, optimiert ist.1. Material for making a conductive organic functional layer on the basis of PEDOT-PSS, wherein the conductivity ubstitution by replacing the solvent that is, by a first solvent S is optimized by a second solvent.
2. Material nach Anspruch 1, bei dem das erste Lösungsmittel Wasser oder ein sonstiges stark polares Lösungsmittel ist.2. Material according to claim 1, wherein the first solvent is water or another strongly polar solvent.
3. Material nach einem der Ansprüche 1 oder 2, bei dem das zweite Lösungsmittel eine glycolhaltige Verbindung wie Ethylenglykol oder ein sonstiger Alkohol ist, insbesondere auch Mischungen mehrerer Alkohole, und/oder Alkohole mit einem3. Material according to one of claims 1 or 2, wherein the second solvent is a glycol-containing compound such as ethylene glycol or another alcohol, in particular also mixtures of several alcohols and / or alcohols with one
Kohlenstoffgehalt von C4 bis CIO, verzweigt und unverzweigt, auch mehrwertige Alkohole, bzw. Gemische daraus, sowie Gemische mit Wasser, besonders bevorzugt Glycol und Glycerol.Carbon content of C4 to CIO, branched and unbranched, also polyhydric alcohols or mixtures thereof, and mixtures with water, particularly preferably glycol and glycerol.
4. Verwendung eines Materials nach einem der vorstehenden Ansprüche zur Herstellung einer Elektrode und/oder einer elektrischen Zuleitung.4. Use of a material according to one of the preceding claims for producing an electrode and / or an electrical feed line.
5. Verwendung nach Anspruch 4, wobei das Material durch Ver- arbeitungsmethoden wie spin-coating, Druckverfahren wie Siebdruck, Tintenstrahldruck, offset, Tampondruck, Flexodruck oder Rakelverfahren aufgebracht wird.5. Use according to claim 4, wherein the material is applied by processing methods such as spin-coating, printing processes such as screen printing, ink-jet printing, offset, pad printing, flexographic printing or knife coating.
6. Verwendung nach einem der Ansprüche 4 oder 5, wobei das Material durch einen Druckprozess strukturiert aufgebracht wird. 6. Use according to one of claims 4 or 5, wherein the material is applied in a structured manner by a printing process.
EP03759849A 2002-06-14 2003-06-12 Material for the production of a conductive organic functional layer and use thereof Withdrawn EP1513902A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10226617 2002-06-14
DE10226617 2002-06-14
PCT/DE2003/001954 WO2003106571A1 (en) 2002-06-14 2003-06-12 Material for the production of a conductive organic functional layer and use thereof

Publications (1)

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EP1513902A1 true EP1513902A1 (en) 2005-03-16

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EP (1) EP1513902A1 (en)
JP (1) JP2005529474A (en)
CN (1) CN1659243A (en)
WO (1) WO2003106571A1 (en)

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EP1638155A1 (en) 2004-09-21 2006-03-22 Samsung SDI Germany GmbH Improvement of the conductivity of a polymer electrode by using an underlying grid of metal lines
JP5052760B2 (en) 2005-04-27 2012-10-17 株式会社フジクラ Manufacturing method of conductive material
GB0510382D0 (en) * 2005-05-20 2005-06-29 Cambridge Display Tech Ltd Ink jet printing compositions in opto-electrical devices
WO2008050801A1 (en) * 2006-10-24 2008-05-02 Mitsubishi Rayon Co., Ltd. Method for making material conductive, method for manufacturing conductive material, and conductive material
JP5162941B2 (en) * 2007-04-05 2013-03-13 コニカミノルタホールディングス株式会社 Transparent conductive film and method for producing the same
JP6426331B2 (en) * 2013-03-13 2018-11-21 マクセルホールディングス株式会社 Transparent conductive coating composition and transparent conductive film
CN104765481B (en) * 2014-01-06 2019-05-28 宸鸿科技(厦门)有限公司 Touch panel and preparation method thereof
US11145921B2 (en) 2017-12-12 2021-10-12 The Regents Of The University Of California Vapor phase photo-electrochemical cell

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EP1081548A1 (en) * 1999-08-30 2001-03-07 Eastman Kodak Company Coating composition containing polythiophene and solvent mixture
KR100847904B1 (en) * 2000-06-26 2008-07-23 아그파-게바에르트 Redispersible latex comprising a polythiophene
US6692662B2 (en) * 2001-02-16 2004-02-17 Elecon, Inc. Compositions produced by solvent exchange methods and uses thereof
DE10111790A1 (en) * 2001-03-12 2002-09-26 Bayer Ag New polythiophene dispersions
US7122130B2 (en) * 2001-12-04 2006-10-17 Agfa Gevaert Composition containing a polymer or copolymer of a 3,4-dialkoxythiophene and non-aqueous solvent

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Title
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US20060081816A1 (en) 2006-04-20
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WO2003106571A1 (en) 2003-12-24

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