CA2148544C - Conductive coatings - Google Patents

Conductive coatings

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Publication number
CA2148544C
CA2148544C CA002148544A CA2148544A CA2148544C CA 2148544 C CA2148544 C CA 2148544C CA 002148544 A CA002148544 A CA 002148544A CA 2148544 A CA2148544 A CA 2148544A CA 2148544 C CA2148544 C CA 2148544C
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CA
Canada
Prior art keywords
radical
groups
c1
electroluminescent
optionally substituted
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.)
Expired - Fee Related
Application number
CA002148544A
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French (fr)
Other versions
CA2148544A1 (en
Inventor
Friedrich Jonas
Alexander Karbach
Bavo Muys
Etienne Van Thillo
Rolf Wehrmann
Andreas Elschner
Ralf Dujardin
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.)
Heraeus Clevios GmbH
Original Assignee
Bayer AG
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Filing date
Publication date
Family has litigation
Priority to DEP4416117.4 priority Critical
Priority to DE4416117 priority
Priority to DE19507413A priority patent/DE19507413A1/en
Priority to DE19507413.0 priority
Application filed by Bayer AG filed Critical Bayer AG
Publication of CA2148544A1 publication Critical patent/CA2148544A1/en
Application granted granted Critical
Publication of CA2148544C publication Critical patent/CA2148544C/en
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25936397&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2148544(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Anticipated expiration legal-status Critical
Application status is Expired - Fee Related legal-status Critical

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Classifications

    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01BCABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124Intrinsically conductive polymers
    • H01B1/128Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
    • 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
    • C08G61/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123Macromolecular 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
    • C08G61/126Macromolecular 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
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D5/24Electrically-conducting paints
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01BCABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124Intrinsically conductive polymers
    • H01B1/127Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01GCAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors [EDLCs]; Processes specially adapted for the manufacture thereof or of parts thereof
    • H01G11/22Electrodes
    • H01G11/30Electrodes characterised by their materials
    • H01G11/48Conductive polymers
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01GCAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors [EDLCs]; Processes specially adapted for the manufacture thereof or of parts thereof
    • H01G11/54Electrolytes
    • H01G11/56Solid electrolytes, e.g. gels; Additives therein
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0034Organic polymers or oligomers
    • H01L51/0035Organic polymers or oligomers comprising aromatic, heteroaromatic, or arrylic chains, e.g. polyaniline, polyphenylene, polyphenylene vinylene
    • H01L51/0036Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H01L51/0037Polyethylene dioxythiophene [PEDOT] and derivatives
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/52Details of devices
    • H01L51/5203Electrodes
    • H01L51/5206Anodes, i.e. with high work-function material
    • 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
    • G02F1/1343Electrodes
    • G02F1/13439Electrodes characterised by their electrical, optical, physical properties; materials therefor; method of making
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0034Organic polymers or oligomers
    • H01L51/0035Organic polymers or oligomers comprising aromatic, heteroaromatic, or arrylic chains, e.g. polyaniline, polyphenylene, polyphenylene vinylene
    • H01L51/0036Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05KPRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00Apparatus or processes for manufacturing printed circuits
    • H05K3/10Apparatus or processes for manufacturing printed circuits in which conductive material is applied to the insulating support in such a manner as to form the desired conductive pattern
    • H05K3/18Apparatus or processes for manufacturing printed circuits in which conductive material is applied to the insulating support in such a manner as to form the desired conductive pattern using precipitation techniques to apply the conductive material
    • H05K3/188Apparatus or processes for manufacturing printed circuits in which conductive material is applied to the insulating support in such a manner as to form the desired conductive pattern using precipitation techniques to apply the conductive material by direct electroplating
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00Enabling technologies or technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10Energy storage
    • Y02E60/13Ultracapacitors, supercapacitors, double-layer capacitors

Abstract

Mixtures of A) neutral polythiophenes of formula (I),

Description

` 2~5~ 1 `_ Conductive coatinqs In the field of electronics there is a requirement for electrically conductive, transparent electrodes, for ex-ample, for LCD displays. Up to the present in most cases glasses or plastic sheets vapour-deposited with metal oxides are employed for these applications. Materials vapour-deposited or sputtered with ITO (indium tin oxide) have particularly good properties. The surface resistance of the ITO layers is of the order of magnitude of less than 500 ~

The production of such layers by sputtering under vacuum is very costly. There is therefore a need for a material which renders possible the production by simple application techniques of transparent coatings having good conductivity.

The production of conductive coatings based on organic conductive materials is known in principle. Thus for example coatings made of polypyrrole (EP-A 302 304) or of polythiophene derivatives (EP-A 440 957) have been described. These coatings can be produced using simple coating processes but they are not sufficiently conductive or transparent for many fields of application.

The present invention provides mixtures of A) neutral polythiophenes of the recurring structural unit of the formula I, R O OR

S

Le A 30 329-Eoreiqn Countries - 1 -2~54~
'_ wherein Rl and R2 independently of one another represent hydrogen or a Cl4 alkyl group or together form an optionally substituted Cl4 alkylene radical, preferably a methylene radical which is option-ally substituted by alkyl groups, an ethylene-1,2 radical optionally substituted by Cll2 alkyl or phenyl groups, or a cyclohexylene-1,2 radical, and B) organic compounds containing dihydroxy or poly-hydroxy and/or carboxyl groups or amide groups or lactam groups.

These mixtures can be applied in thin layers to the substrate and by drying and annealing can be converted into transparent and electrically conducting layers.

Suitable organic compounds cont~; n; ng dihydroxy or polyhydroxy and/or carboxyl groups or amide groups correspond to formula (II) /(H)n R \ (II) (COX)m wherein n and m independently of one another denote an integer from 1 to 20, preferably from 2 to 8 and R denotes a linear, branched or cyclic alkylene radical having 2 to 20 C atoms or an optionally substituted arylene radical having 6 to 14 C
atoms or a heterocyclic radical having 4 to 10 C

Le A 30 329-Forei~n Countries - 2 -i~148544 -atoms or a sugar radical or sugar alcohol radical and X denotes -OH or -NYZ, wherein Y, Z independently of one another represent hydrogen or alkyl, preferably hydrogen or Cl-Cl2-alkYl-Examples of suitable organic compounds containing lactam groups are N-methylpyrrolidone, pyrrolidone, caprolactam, N-methylcaprolactam, N-octylpyrrolidone.

Preferred radicals R are derived from the furan structure or the pyran structure.

Particularly preferred organic compounds corresponding to formula (II) are:

sugar and sugar derivatives such as sucrose, glucose, fructose, lactose; sugar alcohols such as sorbitol, mannitol; furan derivatives such as 2-furancarboxylic acid, 3-furancarboxylic acid; alcohols such as ethylene glycol, glycerol, di- or triethylene glycol.

In addition to water, other protic solvents can also be used as solvents for the polythiophene dispersions accord-ing to the invention, such as for example lower alcoholssuch as methanol, ethanol and isopropanol, as well as mix-tures of water with lower alcohols and other water-miscible organic solvents, such as acetone.

The average particle diameters of the particles in the dispersion can be up to 10 um, preferably up to 3 ,um and most preferably up to 1 ,um.

The polythiophenes of the recurring structural unit of the formula (I) are known (cf. EP-A 440,958 and 339,340). The preparation of the dispersions or solutions according to Le A 30 329-Eoreiqn Countries - 3 -21 18~4'1 -the invention is described in EP-A 440,958 and DE-OS 42 11 459.

The polythiophenes are preferably used in the dispersion or solution in a cationic form, i.e. in the form in which they are obtained for example by treating the neutral thiophenes with oxidising agents. Known oxidising agents, such as potassium peroxodisulphate are used for the oxidation. As a result of oxidation the polythiophenes acquire positive charges which are not shown in the formulae, since the number thereof and their positions cannot be accurately determined.

The number of recurring structural units of the formula (I) is generally >5.

The polythiophene dispersions or solutions according to the invention contain, based on the sum of polythiophene cations and polyanions, that is, based on the total solids content of the solution, from 1 to 100,000% by weight, preferably 10 to 1,000% by weight, of the compounds of formula (II) containing hydroxy and carboxyl groups.
Preferably compounds of formula (II) which are soluble in water are employed.

Organic, polymeric binders and/or organic, low-molecular cross-linking agents may also be added to the coating solutions according to the invention. Appropriate binders are described, for example, in EP-A 564 911.

Epoxysilanes, of the kind described in EP-A 564 911, can be added to the coating solutions according to the invention, particularly for the production of adhesive layers on glass.

The coatings according to the invention can be produced by known methods, for example, by spraying, application by a Le A 30 329-Foreiqn Countries - 4 -~148S4~
-doctor blade, dipping, application with roller applicator systems, by printing processes such as gravure printing, silk screen printing, curtain casting, and can be dried at room temperature or at temperatures of up to 300C, preferably up to 200C.

The coatings according to the invention can be annealed in order to increase electrical conductivity. Annealing can follow drying at temperatures of below 100C and can be combined with drying at temperatures of above 100C. This annealing is carried out at temperatures of from 100C to 400C, preferably at temperatures of up to 250C. The duration of the annealing is between 0.5 and 3600 seconds, and preferably 1 ànd 90 seconds.

The thickness of the coatings according to the invention, depending on the intended use and requirements as to transparency and conductivity, is from 0.025 to 250 um, preferably from 0.05 to 10 ~m; the surface resistance is generally from 0.1 to 2000 D / O, preferably from 1 to 300 D/O.

The coatings according to the invention are used in areas which require good electrical conductivities, for example, as electrodes in electroluminescent displays, in LCD
displays, in solid electrolyte capacitors, for the deposition of metals such as copper, nickel, for example, in the manufacture of printed circuits, in solar cells, in electrochromic displays or for the screening of electromagnetic radiation or for leading away electrical charges, for example, in picture tubes or as anticorrosive coatings on metals, for the production of touch screens.
Other areas of application are systems for picture production, for example, silver halide photography, dry-plate systems, electrophotography.

Le A 30 329-Forei~n Countries - 5 -2~485~

_ The conductive layers can optionally be coated with further layers, for example, W-curing coatings or organic or inorganic scratch-resistant coatings.

The layers according to the invention can be applied to organic and inorganic substrates. Examples of suitable inorganic substrates are glass, oxides or oxidic or non-oxidic ceramics such as aluminium oxide, silicon nitride.
Examples of suitable organic substrates are sheets or other mouldings of pure organic polymers, copolymers or mixtures of, for example, polycarbonate, polystyrene, polyacrylates, polyesters such as polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyamides, polyimides, optionally glass-fibre reinforced epoxy resins, cellulose derivatives such as cellulose triacetate, polyolefins such as polyethylene, polypropylene.

The invention also relates to electroluminescent systems which contain the polythiophene dispersions according to the invention in the form of a transparent conductive layer or electrode.

The electroluminescent systems according to the invention consist of an upper and a lower electrode, between which an electroluminescent layer and optionally other auxiliary layers, such as for example charge-injecting layers are inserted, and they are characterised in that they contain as the electrode a conductive layer consisting of the po-lythiophene mixtures according to the invention.

The electroluminescent system can contain one or more elec-trodes, the conductive layers of which contain the abovementioned polythiophene dispersions. The conductive layers are preferably transparent.

The conductive layer can be integrated in various positions in the structure of the electroluminescent systems. The Le A 30 329-Foreiqn Countries - 6 -~148544 conductive layer can be applied for example in the form of a transparent conductive electrode between a transparent substrate and an electroluminescent layer.

For this purpose the mixtures according to the invention are applied in the form of a film to a suitable substrate in the systems according to the invention.

Suitable substrates are transparent substrates such as glass or plastic films (e.g. polyesters, such as polye-thylene terephthalate or polyethylene naphthalate, poly-carbonate, polyacrylate, polysulphone or polyimide film).

The polythiophene mixture according to the invention is distributed evenly on the substrate by techniques such as spin-coating, casting, application by a doctor blade, prin-ting, curtain casting, etc.

After the film has dried the substrate thus coated can be subjected to a temperature of 150-250C for at least 1 sec, generally 30 secs. This annealing step increases the con-ductivity of the layer.

The thickness of the transparent conductive electrode is 5 nm to several ,um, preferably 10 nm to 1500 nm.

An electroluminescent layer is applied to this conductive transparent electrode in the form of a thin film. The substances described for example in EP-A 443,861 can be used as electroluminescent substances.

After the EL layer has dried it is coated with a counter-electrode. This consists of a conductive substance which can be transparent. Preferably metals such as Al, Au, Ag etc. or alloys or oxides thereof are suitable, which are applied by techniques such as vapour deposition, sputtering or platinisation.

Le A 30 329-Foreiqn Countries - 7 -2~ 48S4~

The system according to the invention is brought into con-tact with the two electrodes by two electrical supply leads (such as for example metal wires).

When direct voltage in the range of 2 to 100 volt is ap-plied the systems emit light of a wavelength of 400 to 700 nm. They display photoluminescence in the range from 400 to 700 nm.

The electroluminescent layer can contain one or more elec-trooptically active substances. It also optionally con-tains customary additives such as inert binders, charge-carrier-transporting substances and mixtures of inert bin-ders and charge-carrier-transporting substances. Charge-carrier-transporting substances increase the electrolumi-nescent intensity and reduce the inception voltages.

Suitable inert binders are preferably soluble, transparent polymers, such as for example polycarbonates, polystyrene and copolymers of polystyrene such as SAN, polysulphones, polyacrylates, polyvinylcarbazole, and vinyl acetate and vinyl alcohol polymers and copolymers, etc.

One or more intermediate layers can be additionally ar-ranged between the electroluminescent systems and the electrodes. These intermediate layers - charge-carrier-transporting substances - are known (for example from Appl.
Phys. Lett. 57 (1990)531) and are defined therein as HTL
(hole transport layer) and ETL (electron transport layer).

The conductive layers can also be applied as transparent conductive electrodes to form a covering layer on an elec-troluminescent layer.

Contrary to the arrangement described above, in which the mixture according to the invention is arranged between an electroluminescent layer and a transparent substrate, the Le A 30 329-Foreiqn Countries - 8 -214~54 1 substance according to the invention can also be used as a covering electrode.

In this use the electroluminescent substance is arranged on a conductive or conductively coated substrate, such as for example metal plates or metal coatings applied by vapour deposition. The substance according to the invention is applied to the electroluminescent layer in the manner des-cribed above.

The advantage of this structure is that it also allows electroluminescent layers which are exposed to high tempe-ratures during their production to be provided with a rea-dily applicable, transparent, conductive electrode.
Example: luminescent plates produced from a luminescent enamel based on ZnS.

The mixtures according to the invention can also be used as a charge-transporting intermediate layer in polymeric lumi-nescent diodes. This intermediate layer increases the efficiency of the systems.

The mixture according to the invention is applied in the abovementioned manner in the form of an intermediate layer.
The intermediate layer can be arranged:
- between the transparent conductive electrode and the electroluminescent polymeric layer, - between the electroluminescent polymeric layer and the 25covering electrode.

The thickness of the intermediate layer is about 3-200 nm, and generally between 10 - 100 nm, and most preferably about 10 nm.

Le A 30 329-Forei~n Countries - 9 -2148~44 -ExamPles A) Preparation of a 3,4-polyethylene dioxythiophene solution 20 g of free polystyrene sulphonic acid (Mn approx.
40,000), 13.0 g of potassium peroxydisulphate and 50 mg of iron(III) sulphate are stirred together in 2000 ml of water. 5.6 g of 3,4-ethylene dioxythiophene is added with stirring. The solution is stirred for 24 h at room temperature. Then 100 g of an anion exchanger (commercial product from Bayer AG, Lewatit MP 62) and 100 g of a cation exchanger (commercial product from Bayer AG, Lewatit S
100), both moistened by water, are added and stirred for 8 hours.

The ion exchangers are removed by filtration. A solution having a solids content of approximately 1.2% by weight is obtained, which is ready for use.

Exam~le 1:

10.0 g of the solution prepared in Example A) together with 10 g of isopropanol are mixed with each of the quantities of sorbitol and 3-glycidoxypropyltrimethoxysilane (com-mercial product A 187 Union Carbide) given in the Table.
The mixture is applied to glass plates and dried in air (approx. 400 mg/m2 dry).

The surface resistance of the dried layers is determined.
The coated glass plates are then placed for 90 seconds on a hot plate at a temperature of 200C and the surface resistance is again determined after cooling.

Le A 30 329-Foreign Countries - 10 -2148~44 -Table:

A 187 Sorbitol Surface resistance [Q/O]
[g] [g] beforeafter annealing 0.2 _ 3500 3500 0.1 0.2 3400 120 0.2 0.2 3500 180 0.4 0.2 3300 300 0.1 0.6 4000 90 0.2 0.6 3800 105 0.4 0.6 3950 125 It is apparent from the Table that the process according to the invention results in significantly superior conductive coatings than does the 3,4-polyethylene dioxythiophene solution without additives and annealing.

Example 2: An electroluminescent system B) Preparation of the coating solution 3.0 g of sorbitol are dissolved with stirring in 50 g of solution A. Then 50 g of isopropanol are added dropwise with stirring and 0.5 g of glycidoxypropyl trimethoxysilane (A 187 = a trade product of Union Carbide) is added.

C) Preparation of the 3,4-polyethylenedioxythiophene electrode Solution B is applied to a glass slide (20 X 30 mm2). The substrate is then rotated in a coating centrifuge for 10 seconds at 500 r.p.m. The substrate coated with the film is placed on a heating plate of a temperature of 180C for 60 seconds, during which the surface resistance is reduced to 80 Q/O. The layer thickness of the film is 1.3 ~m. The film is transparent in the visible region of the spectrum.

Le A 30 329-Foreign Countries - 11 -2~8541 -The electroluminescent polymer is then applied to this layer.

D) Application of an electroluminescent layer to the 3,4-polyethylenedioxythiophene electrode The electroluminescent material used is MEH-PPV (methoxy-ethylhexyloxy phenylenevinylene) known from the literature.
A 0.75% solution of the polymer in chloroform is distributed on the polythiophene-coated substrate of Ex-ample 2C) for 10 seconds at 2000 r.p.m. using a coating centrifuge. Al point contacts are then applied to the polymer film of a thickness of 130 nm by vapour deposition.

E) Use of the flexible polymeric luminescent diodes When the positive contact of a voltage source is connected to the PEDT layer and the negative contact with the Al, a current flows through the electroluminescent polymer. At the same time electroluminescence occurs. The luminescent intensity is proportional to the diode current and increa-ses as the voltage increases.

Le A 30 329-Foreiqn Countries - 12 -

Claims (6)

1. A mixture of (A) a neutral polythiophene having a recurring structural unit of the formula (I), wherein R1 and R2 independently of one another represent hydrogen or a C1-4 alkyl group or together form an optionally substituted C1-4 alkylene radical, or a cyclohexylene-1,2 radical, and B) an organic compound containing a dihydroxy, polyhydroxy, carboxyl, amide or lactam group.
2. A mixture according to claim 1, wherein B) is an organic compound of the formula (II) wherein n and m independently of one another denote an integer from 1 to 20, and R denotes a linear, branched or cyclic alkylene radical having 2 to 20 C atoms or an optionally substituted arylene radical having 6 to 14 C atoms or a heterocyclic radical having 4 to 10 C atoms or a sugar radical or sugar alcohol radical and X denotes -OH or -NYZ, wherein Y, Z independently of one another represent hydrogen or alkyl.
3. A use of a mixture according to claim 1 in the preparation of a conductive coating.
4. A conductive coating containing a mixture according to claim 1, which has been annealed to increase the conductivity thereof.
5. A conductive coating according to claim 4, wherein the surface resistance is less than 300.OMEGA./?.
6. An electroluminescent system comprising an upper and a lower electrode, having an intermediate electroluminescent layer wherein the electrode comprises a conductive layer formed from a mixture according to claim 1.
CA002148544A 1994-05-06 1995-05-03 Conductive coatings Expired - Fee Related CA2148544C (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DEP4416117.4 1994-05-06
DE4416117 1994-05-06
DE19507413A DE19507413A1 (en) 1994-05-06 1995-03-03 conductive coatings
DE19507413.0 1995-03-03

Publications (2)

Publication Number Publication Date
CA2148544A1 CA2148544A1 (en) 1995-11-07
CA2148544C true CA2148544C (en) 1999-10-26

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