WO2007134616A1 - Method for the production of a layer of organic material - Google Patents

Method for the production of a layer of organic material Download PDF

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Publication number
WO2007134616A1
WO2007134616A1 PCT/EP2006/004768 EP2006004768W WO2007134616A1 WO 2007134616 A1 WO2007134616 A1 WO 2007134616A1 EP 2006004768 W EP2006004768 W EP 2006004768W WO 2007134616 A1 WO2007134616 A1 WO 2007134616A1
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WIPO (PCT)
Prior art keywords
layer
solution
organic material
providing
reflowing
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PCT/EP2006/004768
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English (en)
French (fr)
Inventor
Tom Aernouts
Frederik Christian Krebs
Peter Vanlaeke
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Interuniversitair Microelektronica Centrum vzw IMEC
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Interuniversitair Microelektronica Centrum vzw IMEC
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Priority to PCT/EP2006/004768 priority Critical patent/WO2007134616A1/en
Priority to US12/299,765 priority patent/US8216633B2/en
Priority to JP2009510365A priority patent/JP5138677B2/ja
Priority to PCT/EP2007/004491 priority patent/WO2007134823A1/en
Priority to DK07725398.7T priority patent/DK2018675T3/da
Priority to AT07725398T priority patent/ATE485603T1/de
Priority to ES07725398T priority patent/ES2354470T3/es
Priority to EP07725398A priority patent/EP2018675B1/en
Priority to DE602007009970T priority patent/DE602007009970D1/de
Publication of WO2007134616A1 publication Critical patent/WO2007134616A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10Deposition of organic active material
    • H10K71/12Deposition of organic active material using liquid deposition, e.g. spin coating
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/111Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211Fullerenes, e.g. C60
    • 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
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy
    • Y02E10/549Organic PV cells
    • 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
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the present invention relates to the field of organic materials for use in photovoltaic applications.
  • organic materials is meant materials comprising carbon.
  • Photovoltaic applications based on organic materials are known from numerous publications. More specifically a device concept in which the photovoltaic active layer comprises a mixture of an electron donating and an electron accepting material sandwiched between two electrodes is attracting much attention. Compounds forming this mixture for the photovoltaic active layer are manifold. Well-known electron acceptor materials are fullerenes and/or fullerene derivatives. However, other compounds like, for example, cyano-substituted conjugated polymers or perylene based small molecules are also considered as electron acceptors.
  • Well-known electron donating materials are conjugated polymers like, for example, poly(phenylene-vinylene)s, poly(fluorene)s, poly(thienylene-vinylene)s or poly(thiophene)s.
  • other organic polymers as well as numerous amounts of small molecules are also considered as electron donating materials.
  • a combination of poly(thiophene) polymers with fullerene derivatives as photovoltaic active layer is well-known. Especially the ability of having regioregular poly(thiophene) incorporated in the active compound mixture can lead to a better overlap of the absorption characteristics of the photovoltaic active layer with the solar spectrum. A shift of the absorption of such a photovoltaic active layer into the longer wavelength range has been described to be beneficial for the performance of the final solar cell. It can be achieved by incorporating an additional treatment into the device production process, as shown in WO 2004/025746 and in "Effects of Postproduction Treatment on Plastic Solar Cells", Franz Padinger et al., Adv. Funct. Mater. 2003, 13, No. 1 , January.
  • an organic material is deposited on a lower electrode layer of an organic electronic device prior to fabrication of organic layers.
  • the organic layer is allowed to dry into a film.
  • the device is subjected to postprocessing at high temperature and/or high humidity environment to induce reflow of the film.
  • the conductive polymer layer is deposited on the substrate and as it is drying, the substrate is exposed to high temperature and/or high humidity.
  • the photovoltaic active layer of these devices generally has a thickness below 1 micrometer and is sandwiched in between two metallic contacts or contact layers, high accuracy on the deposition of this layer is required. Especially the need to achieve a fully continuous film between the electrodes with a well-controlled thickness and minor surface roughness is high. If the thickness of the film is not uniform, the collection of the photo-generated current through the thinner parts of the film is more efficient than trough the thicker parts of the film. This would leave less of the film that is actually usable in terms of device performance. Moreover, non-uniformities in the film due to high surface roughness or discontinuities in the film due to pinholes can act as low resistance paths and result in high leakage currents.
  • the present invention has been made in view of the above and an object of the present invention is therefore to provide a method to deposit an organic layer with a thickness suitable for photovoltaic applications.
  • the deposition may be performed by a linear technique, a linear casting or linear printing technique.
  • the requested high quality of a fully continuous film with minor surface roughness is obtained.
  • the line resolution and edge definition of the deposited film are substantially improved.
  • the need for additional treatments of the photovoltaic layer to optimize the performance of the final photovoltaic device is not disregarded by this novel method according to the present invention.
  • a method according to embodiments of the present invention comprises the application of an anneal step on an applied photovoltaic active layer, i.e. layer of organic material, before the layer of organic material has dried out completely, e.g. preferably right away or as soon as possible after the deposition of this layer onto the substrate under deposition conditions and before the solvent has completely evaporated from the deposited layer.
  • the layer of organic material is made to reflow.
  • Reflow may be defined as the redistribution of material on the deposition surface i.e. the substrate. This considerably improves the macro quality of the film, leading to obtaining a fully continuous film with minor surface roughness and an accurate line resolution and edge definition.
  • the "macro quality” is a measure for the surface roughness and line resolution accuracy.
  • the surface roughness of the film can be defined by the average thickness deviation (average of the absolute value of the amplitude) of a line drawn along the surface of the film from the intended surface of the film.
  • the surface roughness can be below 1 micron, below 100 nm, below 10 nm.
  • the resolution accuracy of the film can be defined by an average deviation (average of the absolute value of the amplitude) of the edge profile from the intended edge profile.
  • the resolution accuracy of the film can be below 1 mm, below 100 micron, below 10 micron, below 1 micron.
  • the drying step is performed during less than 60 seconds, preferably less than 30 seconds, still more preferred less than 10 seconds. In more preferred embodiments, the anneal step is performed during a time period not longer than a few seconds, preferably between 0.1 and 10 seconds.
  • the drying performed after the anneal can preferably follow a predetermined drying scheme, comprising at least 1 deceleration of the evaporation of the solvent, and thus dry-out of the film, but optionally also followed by a number (1 or more) of accelerations and decelerations.
  • the drying scheme can be optimized in order to provide an appropriate light absorption spectrum of the organic layer.
  • the deceleration takes until an optimum value has been reached for the absorption spectrum of the layer. This considerably improves the micro quality of the film. Micro-quality is related to the internal structure of the layer, i.e. how molecules align.
  • An aspect of the invention is also to provide a method to control the viscosity of the dissolved active layer compounds in the solvent.
  • the viscosity of the dissolved active layer compounds in the solvent is controlled via temperature, choice of solvent, stirring or in any other suitable way. In this way, a solution of the photovoltaic active layer material dissolved in a solvent or solvent mixture can be made suitable for different linear casting or printing techniques.
  • the application of the aforementioned anneal step to improve the film quality can also be done on photovoltaic active layers resulting from a deposition of such viscosity controlled solutions.
  • the present invention also provides a method to induce an increase of the absorption of the photovoltaic layer in the longer wavelength range, described to be beneficial for the performance of the final solar cell.
  • Dissolving the active layer materials in appropriate solvent or solvent mixtures, i.e. solvents or solvent mixtures in which the active layer materials easily dissolve, in combination with a deposition technique like linear casting or printing and controlling its parameters, can thereby make aforementioned additional treatments, e.g. as disclosed in WO 2004/025746, obsolete.
  • the application of the aforementioned anneal step followed by a slow drying step in accordance with the present invention to improve the film quality can still be combined, without deteriorating the final result.
  • a method for producing a layer of organic material comprising 1. providing a substrate; 2. providing a solution, comprising the organic material dissolved in a solvent;
  • the deposition conditions can be normal atmospheric conditions as e.g. in air at atmospheric pressure and room temperature. Deposition can e.g. also be performed in an N 2 atmosphere at atmospheric pressure and room temperature.
  • organic material is meant carbon containing material.
  • the organic material used for the layer can comprise materials which are electron acceptors and/or materials which are electron donors.
  • the organic material may be a mix or combination of electron acceptor and electron donor materials.
  • the layer of organic material may be suitable for being used in solar cell applications, but also for OLED transistors, lasers, phototransistors, photodetectors, optocouplers.
  • the organic material should be a material suitable for the application aimed at. In embodiments of the present invention, the organic material is soluble in tetraline (THN).
  • the organic material may comprise or may be a conjugated polymer. It can comprise or be a regio- regular material.
  • the organic material can comprise or be a poly(thiophene).
  • the organic material can further comprise fullerenes and/or fullerene derivatives.
  • the organic material can further comprise conjugated additives.
  • the organic material can further comprise non-conjugated additives.
  • Conjugated additives can have an electrical function, e.g. providing electrical conductivity.
  • Non-conjugated additives can have function e.g. with regard to printing techniques. They can for instance be used to control the rheology, i.e. characteristics related to deformation and flow of the matter, as e.g. viscosity of the solution, or for instance to allow UV curing of the deposited solution. They can further affect the contact angle, affinity, drying, dilution and so on of the deposited film.
  • Preferred solvents have a high boiling point, because the higher the boiling point of the solvent, for a same temperature and atmosphere, the slower the evaporation and thus the eventual drying out of the film will be.
  • the solvent can comprise tetralin.
  • the solvent can be a mixture of individual solvents. Individual solvents can comprise tetralin, tetrahydrofurane, xylene, toluene, chloroform, chlorobenzene and the like.
  • the solution has a viscosity high enough to prevent bleed through of the solution in a screen printing process, for example a viscosity higher than 0.5 Pa. s.
  • the solution is produced by dissolving the organic material in the solvent and waiting until the solution attains a viscosity high enough to prevent bleed through of the solution in a screen printing process, for example a viscosity higher than 0.5 Pa. s.
  • the ratio of weight of organic material per volume of solution is preferably in the range between, as a bottom limit, 0.5% or 1 % or 2% and, as a top limit, 5% or 6% or 7% or 8% or 9% or 10% or 15%.
  • Providing the layer of solution may preferably be performed by a linear technique, in particular a linear casting technique.
  • the linear casting technique is a doctor-blading technique or a roll-casting technique or a printing technique like, but not limited to, inkjet printing, screen printing, gravure printing, flexographic printing, offset printing.
  • Such techniques can, and preferably do, produce a pattern comprising a top surface and side surfaces, i.e. a three-dimensional pattern.
  • the layer is for example provided by a doctor blading technique.
  • the reflowing may comprise a temperature increase of the layer of organic material.
  • Said reflowing may comprise a temperature increase preferably above the deposition temperature, and up to any temperature lower than the boiling point of the solvent or mixture of solvents, e.g. up to 99%, 90%, 80%, 70%, 60%, 50%, 40%, 30%, 20% of the boiling point temperature in degrees Celcius of the solvent.
  • the reflow can have a duration between, as a lower limit, 0.1 or 1 or 2 or 3 or 4 or 5 seconds and, as an upper limit, 6 or 7 or 8 or 9 or 10 or 15 or 20 or 30 or 60 seconds.
  • the optimum duration will be dependent upon factors such as the chemical and physical properties of the material under reflow, and the environmental conditions during reflow, such as temperature, humidity and pressure conditions, and can be determined by experimentation.
  • the duration of the reflow is of course dependent on the temperature increase: the higher the temperature increase, the faster the layer of organic material will dry out, and the shorter the reflow step should be. It is preferable to have a shorter reflow step at higher temperature, rather than a longer reflow step at lower temperature.
  • the duration of the reflow is of course also dependent on the humidity: the larger the humidity, the faster the layer of organic material will reflow.
  • the reflow can be such that an already partially crystallised organic film, i.e. where the polymer chains are partially lined up in ordered crystals, is again transformed into an amorphous film, i.e. where the polymer chains have no ordered arrangement.
  • the reflow is performed as early as possible after deposition of the layer, in order to be able to change the roughness thereof, preferably immediately after deposition of the layer.
  • the dry out time of the layer, or the evaporation time or evaporation speed of the solvent, after the reflow is controlled.
  • This can be done by state of the art techniques, such as for instance drying out the film in a reduced-temperature environment or in a solvent-saturated environment, or by choosing a specific linear casting technique.
  • linear casting techniques the film is typically dried out after deposition, while with a classical spin-on technique those processes are at least partially occurring contemporaneously.
  • Temperature, pressure, humidity are examples of parameters which may be controlled in order to control the dry-out time of the layer. Controlling the dry-out time of the layer can advantageously be performed by reducing the evaporation speed of the solvent, when compared to the evaporation speed of the solvent at deposition conditions.
  • the drying performed after the anneal can preferably be controlled by following a predetermined drying scheme, comprising at least 1 deceleration of the evaporation of the solvent, and thus controlling the drying-out of the film, but the at least 1 deceleration can optionally also be followed by a number (1 or more) of accelerations and decelerations,
  • the drying scheme can be optimized in order to provide an appropriate light absorption spectrum of the organic layer.
  • the deceleration of the evaporation of the solvent, or thus the drying-out of the film under conditions so that it dries out slower than it would do under deposition conditions takes place until an optimum value has been reached for the absorption spectrum of the layer.
  • the drying scheme can be determined such that the micro quality (quality of microstructure) of the layer is optimised.
  • the term "substrate" may include any underlying material or materials that may be used, or upon which a device, a circuit or an epitaxial layer may be formed.
  • the substrate can be transparent, semi-transparent or opaque.
  • the substrate can comprise glass, quartz, semiconductors (such as silicon, germanium, gallium arsenide, and the like), metals (such as platinum, gold, palladium, indium, silver, cupper aluminium, zinc, chromium nickel, and the like), stainless steel, plastic.
  • the substrate may include for example, an insulating layer such as a SiO 2 or a Si 3 N 4 layer in addition to the previously described substrate materials.
  • the substrate may include in addition to previously described substrate materials electrode materials like metals (such as platinum, gold, palladium, indium, silver, cupper aluminium, zinc, chromium nickel, and the like), metal oxides (such as lead oxide, tin oxide, indium tin oxide, and the like), graphite, doped inorganic semiconductors (such as silicon, germanium, gallium arsenide, and the like) and doped conducting polymers (such as polyaniline, polypyrrole, polythiophene, and the like).
  • substrate is thus used to define generally the elements for layers that underlie a layer or portions of interest. Also, the "substrate” may be any other base on which a layer is formed, for example a glass or metal layer.
  • the method according to embodiments of the present invention can be used for the production of an organic layer as part of a photovoltaic cell, a light- emitting diode, a photodetector, a transistor, a laser or a memory element.
  • the layer of organic material produced by a method according to embodiments of the present invention can advantageously be used for the production of a solar cell.
  • Such a method for production of a solar cell preferably comprises:
  • Fig. 1 illustrates films, after full evaporation of the solvent, of P3HT, screen printed onto a substrate (a) without reflow treatment in accordance with prior art methods, and (b) with a reflow treatment in accordance with embodiments of the present invention, the reflow treatment having a duration of 2 seconds at a temperature of 100 0 C.
  • Fig. 2 shows optical absorption spectra (UltraViolet-Visual spectra) of a spin coated and a doctor bladed film containing a mixture of the regio-regular conjugated polymer P3HT and the molecule PCBM.
  • aspects of the invention concern a temperature treatment, also called anneal step, of a wet layer comprising organic material, in order to obtain a reflow effect of a layer deposited by linear casting or printing techniques.
  • This has as advantage that it enhances the film quality so as to obtain a fully continuous film with minor surface roughness and accurate line resolution and edge definition. More specifically it has been shown beneficial for the production of active layers for organic material based solar cells.
  • the anneal step is followed by a controlled drying step of the layer of organic material, so that the drying of the layer is slowed down with regard to drying under deposition conditions, at least during a pre-determined period in time.
  • An organic material has been dissolved in a solvent. Deposition of this solution onto a substrate by use of the linear casting or printing technique can yield a thin, inhomogeneous film with a thickness below 1 micron, the film having poor resolution definition after evaporation of the solvent, i.e. the film showing a deviation from the required pattern which is larger than 1 mm.
  • this anneal step is highly compatible with the next step of controlled drying of the film, in such a way that the drying is performed slower than it would be performed under deposition conditions.
  • the system is not brought back to deposition conditions, but to drying conditions different from the deposition conditions so as to control the drying of the film.
  • the drying conditions may differ from the deposition conditions e.g. in temperature, pressure, humidity or saturation or the environment.
  • a temperature curing of approximately 100 0 C during ⁇ 2s is then performed in accordance with embodiments of the present invention, the temperature curing being applied after deposition of the solution onto the substrate, and before the solution is completely dried out, preferably the temperature curing being applied immediately after deposition of the solution onto the substrate.
  • the temperature curing is performed under conditions and during a time sufficient to make the layer reflow.
  • the conditions are such that the time of the temperature curing may be as short as possible, less than 60 seconds preferably less than 20 seconds, still more preferred only a few seconds, i.e. between 0.1 and 10 seconds.
  • the temperature curing is followed by a controlled drying of the applied film, so that the film dries slower than it would do if it would dry under deposition conditions. This may e.g. be obtained by changing one or more of the environmental parameters such as temperature, pressure, humidity or saturation.
  • the method of the present invention yields a substantial improvement of the layer quality, both of the macro and of the micro structure.
  • the surface roughness of the film is reduced, the edge definition of the pattern is considerably better, and on a micro-scale the film shows an improved alignment of molecules compared to conventional methods of applying such films, as shown in Fig. 1 by digital scans of the layers processed without (Fig. 1 (a)) or with Fig. 1 (b)) this annealing procedure, after full evaporation of the solvent.
  • a viscosity level can thereby be obtained such that bleed through of the solution in a screen printing process can be prevented.
  • This procedure makes the solution more suitable for processing with a technique like screen printing.
  • the procedure can be reversed simply by heating the solution to obtain again the initial lower viscosity.
  • This reversing of the effect results in a viscosity level of the solution that can be more suitable for other deposition techniques than screen printing.
  • the reversing is accompanied by a disappearance of the red-shifted colour of the solution.
  • the application of the earlier-described annealing procedure on the deposited film will result in improved layer quality of the photovoltaic active layer.
  • the effect of the annealing procedure can, in the case of depositing the solution with a higher viscosity level, clearly be monitored by a colour change of the deposited layer.
  • the red-shifted colour of the highly viscous solution disappears upon annealing of the deposited layer.
  • the evaporation i.e. evaporation speed or time
  • a broadening of the radiation absorption of the photovoltaic layer in the longer wavelength range can be induced. This also improves the layer quality.
  • a slow evaporation speed yields thereby a strong broadening in the longer wavelength range, whereas a fast evaporation of the solvent results in a photovoltaic active layer with reduced absorption in the longer wavelength range.
  • the evaporation of the solvent can also be controlled by dissolving the active layer materials in solvent or solvent mixtures with appropriate boiling points, i.e.
  • a deposition technique like linear casting or printing and controlling its deposition parameters like deposition speed and pressure.
  • the evaporation of the solvent can be fully controlled by an appropriate choice of the solvent or solvent mixture in which the active layer materials are dissolved.
  • the evaporation speed can thereby be lowered when using higher boiling point solvents or solvent mixtures.
  • the increase of the absorption of the photovoltaic active layer in the longer wavelength range is controlled by the use of appropriate solvent in combination with the linear casting or printing technique.
  • the application of the aforementioned reflow step to improve the film quality can still be advantageously combined with this method without deteriorating the final result (even making the final result even better) since the reflow step can be kept limited in time.
  • linear casting techniques allows a good control of the evaporation speed, as evaporation speed is dependent on e.g. ambient parameters which are better controllable with linear casting techniques than with spin-coating techniques.
  • Linear casting techniques allow more process freedom, e.g. the temperature ranges suitable for spin-coating are smaller than for linear casting techniques.
  • linear casting techniques allow reducing the evaporation speed when compared to the classical spin-coating to produce the active layer of organic devices, e.g. containing regioregular conjugated polymers. This can result in a broadening of the absorption spectrum compared to rotation based casting techniques.
  • the deposition mixture contained a 1.5% (weight/volume) 1 :2 weight ratio blend of the regioregular conjugated polymer P3HT and the molecule PCBM dissolved in orthodichlorobenzene + 2.5% (volume %) tetrahydronaphtalene mixture, as used in solar cell devices.
  • the spin-coated film was deposited at 1000 rpm for 60s.
  • the doctor bladed film was deposited at a blade speed of 80 mm/s.
  • UV-Vis UltraViolet-Visual
  • molecular materials e.g. ZnPc (zinc-phthalocyanine), MePtcdi (N, N'-dimethyl-perylene-3,4,9,10-dicarboximide), C ⁇ o, pentacene, oligomeric thiophenes, derivatized compounds of these molecular materials,
  • ZnPc zinc-phthalocyanine
  • MePtcdi N, N'-dimethyl-perylene-3,4,9,10-dicarboximide
  • C ⁇ o pentacene
  • oligomeric thiophenes derivatized compounds of these molecular materials
  • hole-conducting donor type polymers e.g. MDMO-PPV (poly[2- methoxy-5-(3,7-dimethyloctyloxy)]-1 ,4-phenylene-vinylene), P3HT (poly(3-hexylthiophene-2,5-diyl)), PFB (poly(9,9'-dioctylfluorene-co- bis-N,N'-(4-butylphenyl)-bis-N,N'-phenyl-1 ,4-phenylenediamine)), (c) electron-conducting acceptor polymers, e.g.
  • MDMO-PPV poly[2- methoxy-5-(3,7-dimethyloctyloxy)]-1 ,4-phenylene-vinylene
  • P3HT poly(3-hexylthiophene-2,5-diyl)
  • PFB poly(9,9'-dioctyl
  • CN-MEH-PPV poly-[2- methoxy-5-(2'-ethylhexyloxy)-1 ,4-(1-cyanovinylene)-phenylene]
  • F8TB poly(9,9'-dioctlyfluoreneco-benzothiadiazole)
  • a soluble derivative of Ceo namely PCBM (1-(3-methoxycarbonyl)propyl-1- phenyl[6,6]C 6 i).
  • the organic polymers can be, for example, polymers having a conjugated repeating unit, in particular polymers in which neighboring repeating units are bonded in a conjugated manner, such as polythiophenes, polyphenylenes, polythiophenevinylenes, poly(3- alkyl)thiophene, polyfluorenes, or poly-p-phenylenevinylenes or their families, copolymers, derivatives, or mixtures thereof.
  • the organic polymers can be, for example: polyfluorenes; poly-p- phenylenevinylenes, 2-, or 2, 5-substituted poly-p-pheneylenevinylenes; polyspiro polymers; or their families, copolymers, derivatives, or mixtures thereof.
  • the organic polymers can for example include a material capable of charge transport.
  • Charge transport materials include polymers or small molecules that can transport charge carriers.
  • organic materials such as polythiophene, derivatized polythiophene, oligomeric polythiophene, derivatized oligomeric polythiophene, pentacene, compositions including C60, and compositions including derivatized C60 may be used.
  • the described method is not restricted to the THN solvent mentioned but can be widely applicable to many solvents or solvent mixtures.
  • the described method is not restricted to the screen printing or doctor blading method mentioned but is relevant in many solution processes like for example, roll-coating, dip-coating, web-coating, spray-coating or ink jet printing, gravure printing, flexographic printing, offset printing, where thin films are to be deposited with a minor surface roughness and a high quality of line resolution and edge definition.
  • the described method is not restricted to the photovoltaic application mentioned but is relevant for many applications where thin films, i.e. films thinner than 1 micron, are to be deposited with a minor surface roughness and a high quality of line resolution and edge definition like in, for example, organic light-emitting diodes, photodetectors, transistors, lasers, memory elements.

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PCT/EP2006/004768 2006-05-19 2006-05-19 Method for the production of a layer of organic material Ceased WO2007134616A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
PCT/EP2006/004768 WO2007134616A1 (en) 2006-05-19 2006-05-19 Method for the production of a layer of organic material
US12/299,765 US8216633B2 (en) 2006-05-19 2007-05-21 Method for the production of a layer of organic material
JP2009510365A JP5138677B2 (ja) 2006-05-19 2007-05-21 有機材料の層の製造方法
PCT/EP2007/004491 WO2007134823A1 (en) 2006-05-19 2007-05-21 Method for the production of a layer of organic material
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