EP1513902A1 - Matiere servant a produire une couche fonctionnelle organique conductrice et utilisation de cette matiere a cet effet - Google Patents

Matiere servant a produire une couche fonctionnelle organique conductrice et utilisation de cette matiere a cet effet

Info

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Withdrawn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)
English (en)
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
Siemens Corp
Original Assignee
Siemens AG
Siemens 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
Application filed by Siemens AG, Siemens Corp filed Critical Siemens AG
Publication of EP1513902A1 publication Critical patent/EP1513902A1/fr
Withdrawn legal-status Critical Current

Links

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).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Wood Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Conductive Materials (AREA)
  • Thin Film Transistor (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)
  • Electrodes Of Semiconductors (AREA)
  • Photovoltaic Devices (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne une matière destinée à une couche fonctionnelle organique conductrice, en particulier à base de PEDOT-PSS [poly(3,4-éthylènedioxythiophène)-poly(styrène-sulfonate)]. Selon l'invention, la conductivité de cette matière peut être augmentée de façon significative par remplacement du solvant.
EP03759849A 2002-06-14 2003-06-12 Matiere servant a produire une couche fonctionnelle organique conductrice et utilisation de cette matiere a cet effet Withdrawn EP1513902A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10226617 2002-06-14
DE10226617 2002-06-14
PCT/DE2003/001954 WO2003106571A1 (fr) 2002-06-14 2003-06-12 Matiere servant a produire une couche fonctionnelle organique conductrice et utilisation de cette matiere a cet effet

Publications (1)

Publication Number Publication Date
EP1513902A1 true EP1513902A1 (fr) 2005-03-16

Family

ID=29723170

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03759849A Withdrawn EP1513902A1 (fr) 2002-06-14 2003-06-12 Matiere servant a produire une couche fonctionnelle organique conductrice et utilisation de cette matiere a cet effet

Country Status (5)

Country Link
US (1) US20060081816A1 (fr)
EP (1) EP1513902A1 (fr)
JP (1) JP2005529474A (fr)
CN (1) CN1659243A (fr)
WO (1) WO2003106571A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1638155A1 (fr) 2004-09-21 2006-03-22 Samsung SDI Germany GmbH Amélioration de la conductivité d'une électrode en polymère en utilisant une grille sous-jacente de lignes métalliques
JP5052760B2 (ja) * 2005-04-27 2012-10-17 株式会社フジクラ 導電材料の製造方法
GB0510382D0 (en) * 2005-05-20 2005-06-29 Cambridge Display Tech Ltd Ink jet printing compositions in opto-electrical devices
WO2008050801A1 (fr) * 2006-10-24 2008-05-02 Mitsubishi Rayon Co., Ltd. Procédé permettant de rendre une matière conductrice, procédé de fabrication de matière conductrice et matière conductrice
JP5162941B2 (ja) * 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 透明導電性フィルム及びその製造方法
JP6426331B2 (ja) * 2013-03-13 2018-11-21 マクセルホールディングス株式会社 透明導電性コーティング組成物、及び透明導電性膜
CN104765481B (zh) * 2014-01-06 2019-05-28 宸鸿科技(厦门)有限公司 触控面板及其制作方法
US11145921B2 (en) 2017-12-12 2021-10-12 The Regents Of The University Of California Vapor phase photo-electrochemical cell

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1081548A1 (fr) * 1999-08-30 2001-03-07 Eastman Kodak Company Composition de revêtement comprenant du polythiophène et un mélange de solvants
EP1309646B1 (fr) * 2000-06-26 2009-10-07 Agfa-Gevaert Latex redispersible a base de polyothiophene
US6692662B2 (en) * 2001-02-16 2004-02-17 Elecon, Inc. Compositions produced by solvent exchange methods and uses thereof
DE10111790A1 (de) * 2001-03-12 2002-09-26 Bayer Ag Neue Polythiophen-Dispersionen
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03106571A1 *

Also Published As

Publication number Publication date
CN1659243A (zh) 2005-08-24
WO2003106571A1 (fr) 2003-12-24
US20060081816A1 (en) 2006-04-20
JP2005529474A (ja) 2005-09-29

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