EP1514318A2 - Materiau pour couche fonctionnelle d'un composant electronique organique, procede de production et utilisation correspondants - Google Patents

Materiau pour couche fonctionnelle d'un composant electronique organique, procede de production et utilisation correspondants

Info

Publication number
EP1514318A2
EP1514318A2 EP03759828A EP03759828A EP1514318A2 EP 1514318 A2 EP1514318 A2 EP 1514318A2 EP 03759828 A EP03759828 A EP 03759828A EP 03759828 A EP03759828 A EP 03759828A EP 1514318 A2 EP1514318 A2 EP 1514318A2
Authority
EP
European Patent Office
Prior art keywords
solvent
functional polymer
material according
functional
fractions
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Withdrawn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
EP03759828A
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.)
Konarka Technologies Inc
Original Assignee
Konarka Technologies Inc
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 Konarka Technologies Inc filed Critical Konarka Technologies Inc
Publication of EP1514318A2 publication Critical patent/EP1514318A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/60—Forming conductive regions or layers, e.g. electrodes
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the invention relates to a material for a functional layer of an organic electronic component, in particular one from which both a conductive, a semiconducting and an insulating functional layer can be formed.
  • PEDOT-PSS poly (3,4-ethylenedioxythiophene) -poly (styrene-sulfonate)] or PA I (polyaniline) -PSS are known. These materials result in functional layers as thin films of the respective functional polymer.
  • the invention relates to a material for forming a functional layer of an electronic component with adjustable conductivity, the material comprising a mixture of at least two fractions of a functional polymer, namely a first fraction based on a dispersion of the functional polymer in a first solvent which the functional polymer is at least partially dispersed and a second fraction of functional polymer which is based on a real solution of the functional polymer in a second solvent, the two fractions being processed, dispersed and / or dissolved together and by the mixing ratio of the at least two fractions the conductivity of the functional layer formed from this material can be adjusted in connection with the thickness of the functional layer.
  • the invention also relates to a method for producing a material for a functional layer of an electronic component, in which a mixture of two different fractions
  • a dispersion of the functional polymer and a solution of the functional polymer are mixed with high-boiling solvent, then the lower-boiling solvent is removed by distillation in such a way that the various fractions of functional polymer in the high-boiling solvent ultimately essentially form the material.
  • the high-boiling solvent is added in equal parts to the fraction.
  • the material is essentially free of the solvent and / or dispersant of the fractions on which it is based and / or comprises an additional, third solvent.
  • the material can be any other additives and additives such as these types the materials are common and / or useful, such as defoamers or wetting agents etc.
  • the “material *” is always the material according to the invention for forming a functional layer of an organic electronic component.
  • the two fractions are each in dry substance before the dispersion / solution.
  • the two fractions denote two modifications, i.e. two presumably different states of a substance.
  • the functional polymer is PEDOT or PANI.
  • the functional polymer is in the form of a copolymer or mixture which comprises PSS polystyrene sulfonate as anions.
  • the first solvent is water or another high polarity component in which the functional polymer is substantially insoluble.
  • the second solvent ethanol or another low-boiling, polar solvent is preferably a polar-protic, which can form H-bridge bonds.
  • low-boiling * is understood here to mean solvents which have a boiling temperature of up to 150 ° C.
  • the third solvent is different from the first and / or the second solvent.
  • ethylene glycol or another alcohol is used as the third solvent.
  • sets especially also mixtures of several alcohols and / or alcohols with a carbon content of C4 to CIO, branched and unbranched, also polyhydric alcohols, or mixtures thereof, and mixtures with water, particularly preferably glycol and glycerol.
  • solution is used when individual polymer particles are essentially surrounded by solvent molecules and it is in contrast to the term “dispersion”, which denotes the state in which individual polymer particles conglomerate and form clusters, for example, but do not precipitate or settle out, but instead are essentially dispersed and do not form a precipitate, i.e. larger solid agglomerations.
  • a component is referred to here as a solvent or as a dispersing agent only depends on how the functional polymer in question behaves in this agent. The conditions that prevail during production, storage and / or processing must be considered.
  • 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 intended to be widely used, for example silicones, and the term should not 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 historically determined and therefore contains no information about the existence of an actual lent polymeric compound and no statement whether it is a polymer mixture or a copolymer or not.
  • a dry substance is a substance that is essentially free of solvent.
  • An “organic, electronic component *” here is, for example, a transistor, a diode, an optocoupler, a solar cell, an organic light-emitting diode, organic lighting, a display (active and passive matrix), a conductive fabric, an antistatic coating, or an optoelectronic component designated.
  • the conductivity is modified by many orders of magnitude without changing the solvent environment.
  • a mixture of two different PEDOT solutions both with the same solvent, e.g.
  • Ethylene glycol which have different conductivities due to their history (one solution is made from a water-based solution, the other from an ethanol-based solution).
  • the solution obtained from water-based PEDOT (WPEDOT) has a specific resistance of 10 ⁇ 2 ⁇ cm, that from ethanol-based PEDOT (EPEDOT) has a specific resistance of 10 7 ⁇ cm.
  • the surface conductivity can even be varied by 10 orders of magnitude by adjusting the layer thickness (between 5 nm and 500 ⁇ m).
  • a surface resistance is generally given for this.
  • the ITO used for LCDs, OLEDs or solar cells has a sheet resistance of 20 OHM / square as the anode.
  • a Pedot mixture with 10 s / cm (corresponds to 10 "1 Ohm cm specific resistance) achieves these conductive properties with a layer thickness of 5 ⁇ m.
  • the same volume of ethylene glycol is added to the original solutions, which are commercially available, for example, from HC Starck, and then the original solvent is distilled off in a rotary evaporator. Since ethylene glycol can only be distilled at 200 ° C, a pure glycolic PEDOT solution then remains. Since the original materials WPEDOT and EPEDOT are of a different nature, in the case of the WPEDOT the conductivity is drastically reduced by replacing the water with ethylene glycol, which is due to the dispersive nature of the WPEDOT. In the case of the EPEDOT, which is a real solution, the conductivity is not changed by replacing the ethanol with ethylene glycol. This creates two glycolic PEDOT variations with 5 orders of magnitude of different conductivity. By mixing (blending) the two solutions, any conductivity in between can now be set (see Figure 1).
  • the present invention is intended to solve the problem of targeted fine tuning (“tuning *”) of the conductivity of the polymer film over many orders of magnitude while maintaining the optimum solution or dispersion properties for the coating process.
  • This invention makes it possible to use a low-cost coating method, such as a polymer film, the conductivity of which can be chosen in a wide range.
  • the invention relates to a material (polymer mixture) for forming a thin layer (5 nm to 500 ⁇ m) with adjustable conductivity.
  • the material comprises at least a mixture of two different fractions of a functional polymer, preferably in a solvent.
  • the invention relates to a material for applying thin organic layers with conductivity that can be set in a defined manner.
  • the material comprises at least a mixture of two different fractions of a functional polymer, preferably in a solvent, and comes e.g. as a functional layer of an organic electronic component by means of various application techniques.

Landscapes

  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Conductive Materials (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Electroluminescent Light Sources (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Paints Or Removers (AREA)
  • Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
  • Thin Film Transistor (AREA)
  • Formation Of Insulating Films (AREA)

Abstract

La présente invention concerne un matériau permettant d'appliquer des couches organiques minces qui présentent une conductivité pouvant être réglée de manière définie. Ce matériau comprend au moins un mélange de deux fractions différentes d'un polymère fonctionnel, de préférence dans un solvant, et est utilisé par exemple comme couche fonctionnelle d'un composant électronique organique à l'aide de différentes techniques d'application.
EP03759828A 2002-06-14 2003-06-05 Materiau pour couche fonctionnelle d'un composant electronique organique, procede de production et utilisation correspondants Withdrawn EP1514318A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10226669 2002-06-14
DE10226669 2002-06-14
PCT/DE2003/001867 WO2003107453A2 (fr) 2002-06-14 2003-06-05 Materiau pour couche fonctionnelle d'un composant electronique organique, procede de production et utilisation correspondants

Publications (1)

Publication Number Publication Date
EP1514318A2 true EP1514318A2 (fr) 2005-03-16

Family

ID=29723179

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03759828A Withdrawn EP1514318A2 (fr) 2002-06-14 2003-06-05 Materiau pour couche fonctionnelle d'un composant electronique organique, procede de production et utilisation correspondants

Country Status (5)

Country Link
US (2) US7871543B2 (fr)
EP (1) EP1514318A2 (fr)
JP (1) JP2005530351A (fr)
CN (1) CN1663061A (fr)
WO (1) WO2003107453A2 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003107453A2 (fr) * 2002-06-14 2003-12-24 Siemens Aktiengesellschaft Materiau pour couche fonctionnelle d'un composant electronique organique, procede de production et utilisation correspondants
WO2003107454A2 (fr) * 2002-06-14 2003-12-24 Siemens Aktiengesellschaft Materiau destine a une couche fonctionnelle mince et faiblement conductrice pour une oled et procede de fabrication
GB0510382D0 (en) 2005-05-20 2005-06-29 Cambridge Display Tech Ltd Ink jet printing compositions in opto-electrical devices
CN101828280B (zh) * 2007-10-18 2013-03-27 默克专利股份有限公司 导电配制剂
DE102008039337A1 (de) 2008-03-20 2009-09-24 Siemens Aktiengesellschaft Vorrichtung zum Besprühen, Verfahren dazu sowie organisches elektronisches Bauelement
JP5340656B2 (ja) 2008-07-02 2013-11-13 シャープ株式会社 太陽電池アレイ
JP5215150B2 (ja) * 2008-12-05 2013-06-19 トッパン・フォームズ株式会社 非接触型データ受送信体
JP6015073B2 (ja) * 2012-04-02 2016-10-26 セイコーエプソン株式会社 機能層形成用インク、発光素子の製造方法

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3634281A1 (de) 1986-10-08 1988-04-21 Basf Ag Elektrisch leitfaehige polysilane
DE4100202A1 (de) 1990-02-08 1991-08-14 Bayer Ag Neue polythiophensalze, ihre herstellung und ihre verwendung zur herstellung leitfaehiger schichten und ihre verwendung dieser schichten als elektroden
US5232631A (en) * 1991-06-12 1993-08-03 Uniax Corporation Processible forms of electrically conductive polyaniline
DE19841803A1 (de) 1998-09-12 2000-03-16 Bayer Ag Hilfsschichten für elektrolumineszierende Anordnungen
JP3629973B2 (ja) 1998-09-16 2005-03-16 松下電器産業株式会社 導電性組成物及びコンデンサの製造方法
EP1081548A1 (fr) 1999-08-30 2001-03-07 Eastman Kodak Company Composition de revêtement comprenant du polythiophène et un mélange de solvants
US6372154B1 (en) * 1999-12-30 2002-04-16 Canon Kabushiki Kaisha Luminescent ink for printing of organic luminescent devices
US6605483B2 (en) 2000-04-27 2003-08-12 Add-Vision, Inc. Screen printing light-emitting polymer patterned devices
WO2003107453A2 (fr) * 2002-06-14 2003-12-24 Siemens Aktiengesellschaft Materiau pour couche fonctionnelle d'un composant electronique organique, procede de production et utilisation correspondants
US20020038999A1 (en) 2000-06-20 2002-04-04 Yong Cao High resistance conductive polymers for use in high efficiency pixellated organic electronic devices
DE10103416A1 (de) 2001-01-26 2002-08-01 Bayer Ag Elektrolumineszierende Anordnungen
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
EP1453877B1 (fr) * 2001-12-04 2007-03-28 Agfa-Gevaert Procede de preparation d'une solution ou une dispersion aqueuse ou non aqueuse d'un polythiophene ou d'un copolymere de thiophene
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 WO03107453A2 *

Also Published As

Publication number Publication date
CN1663061A (zh) 2005-08-31
WO2003107453A3 (fr) 2004-05-21
US8696941B2 (en) 2014-04-15
US20060011894A1 (en) 2006-01-19
US20110095236A1 (en) 2011-04-28
JP2005530351A (ja) 2005-10-06
WO2003107453A2 (fr) 2003-12-24
US7871543B2 (en) 2011-01-18

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