WO2012053400A1 - Procédé de production d'éléments de conversion photoélectrique - Google Patents

Procédé de production d'éléments de conversion photoélectrique Download PDF

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Publication number
WO2012053400A1
WO2012053400A1 PCT/JP2011/073388 JP2011073388W WO2012053400A1 WO 2012053400 A1 WO2012053400 A1 WO 2012053400A1 JP 2011073388 W JP2011073388 W JP 2011073388W WO 2012053400 A1 WO2012053400 A1 WO 2012053400A1
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WIPO (PCT)
Prior art keywords
photoelectric conversion
conversion element
ink
organic layer
ink film
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PCT/JP2011/073388
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English (en)
Japanese (ja)
Inventor
一 桑原
崇広 清家
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住友化学株式会社
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Publication of WO2012053400A1 publication Critical patent/WO2012053400A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41F—PRINTING MACHINES OR PRESSES
    • B41F3/00—Cylinder presses, i.e. presses essentially comprising at least one cylinder co-operating with at least one flat type-bed
    • B41F3/18—Cylinder presses, i.e. presses essentially comprising at least one cylinder co-operating with at least one flat type-bed of special construction or for particular purposes
    • B41F3/20—Cylinder presses, i.e. presses essentially comprising at least one cylinder co-operating with at least one flat type-bed of special construction or for particular purposes with fixed type-beds and travelling impression cylinders
    • B41F3/22—Cylinder presses, i.e. presses essentially comprising at least one cylinder co-operating with at least one flat type-bed of special construction or for particular purposes with fixed type-beds and travelling impression cylinders with more than one type-bed
    • 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
    • H10K85/151—Copolymers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K39/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00
    • H10K39/30—Devices controlled by radiation
    • H10K39/32—Organic image sensors
    • 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 present invention relates to a photoelectric conversion element and a method for producing the same, and a solar cell module and an organic photosensor provided with the photoelectric conversion element.
  • the photoelectric conversion element includes a pair of electrodes and one or more organic layers provided between the electrodes.
  • There are various methods for forming the organic layer one of which is a coating method.
  • a coating method an ink containing a material for forming an organic layer is applied and formed on a substrate by a predetermined method, and the formed ink is solidified to form an organic layer.
  • a flexographic printing method has been proposed as a method for coating and forming the ink (see, for example, Patent Document 1).
  • an ink is formed on a printing plate made of polycarbonate, and the formed ink is transferred to a predetermined substrate to form an organic layer.
  • an object of the present invention is to provide a method for producing a photoelectric conversion element capable of forming a flat organic layer by a printing method.
  • the present invention provides the following [1] to [12].
  • [1] A method for producing a photoelectric conversion element comprising a pair of electrodes and one or more organic layers provided between the pair of electrodes, Preparing a substrate provided with one of the pair of electrodes; An ink containing the material of the organic layer is applied to a transfer body provided with a member made of silicone rubber on the surface portion, an ink film is formed on the transfer body, and the ink film is transferred to the substrate. Forming the organic layer; Forming a second electrode of the pair of electrodes.
  • a method for manufacturing a photoelectric conversion element comprising a pair of electrodes and one or more organic layers provided between the pair of electrodes, Preparing a substrate provided with one of the pair of electrodes; An ink containing the material of the organic layer is applied to a transfer body provided with a member made of silicone rubber on the surface portion, an ink film is formed on the transfer body, and the ink film is transferred to the substrate. Forming the organic layer; Forming a second
  • step of forming the organic layer further includes a step of drying the ink film before transferring the ink film formed on the transfer body to the substrate.
  • the step of forming the organic layer further includes a step of patterning the ink film by removing a predetermined portion of the ink film before transferring the ink film to the substrate.
  • the manufacturing method of the photoelectric conversion element of description is a step of patterning the ink film by removing a predetermined portion of the ink film before transferring the ink film to the substrate.
  • the photoelectric conversion element has an active layer as the organic layer, and the active layer is formed by the step of forming the organic layer. 6] The manufacturing method of the photoelectric conversion element as described in any one of.
  • the active layer has a thin film containing an electron donating compound material and a thin film containing an electron accepting compound material,
  • the photoelectric conversion element has two or more active layers as one or more organic layers, and an intermediate electrode layer provided between the active layers, Each of the active layers is formed by the step of forming the organic layer, and the intermediate electrode layer is formed between the steps of forming the active layer, according to any one of [1] to [8] The manufacturing method of the photoelectric conversion element of description.
  • a photoelectric conversion element that can be manufactured by the manufacturing method according to any one of [1] to [9].
  • a photovoltaic power generation module including the photoelectric conversion element according to [10].
  • a photoelectric conversion element including an organic layer having a flat surface can be formed.
  • FIG. 1 is a schematic diagram of a printing apparatus.
  • FIG. 2 is a schematic cross-sectional view of the blanket cylinder and the coating unit.
  • a method for producing a photoelectric conversion element according to the present invention is a method for producing a photoelectric conversion element comprising a pair of electrodes and one or more organic layers provided between the pair of electrodes, the method comprising: A step of preparing a substrate on which one electrode is provided; and a transfer body provided with a member made of silicone rubber on the surface thereof, an ink containing the material of the organic layer is applied to form a film, and the ink is applied to the transfer body. Forming a film, transferring the ink film to the substrate to form the organic layer, and forming the other electrode of the pair of electrodes.
  • the photoelectric conversion element includes a pair of electrodes composed of an anode and a cathode, and one or more organic layers provided between the pair of electrodes.
  • a photoelectric conversion element can be manufactured by sequentially laminating each layer constituting these photoelectric conversion elements on a predetermined substrate.
  • the photoelectric conversion element includes at least one active layer as an organic layer.
  • the photoelectric conversion element may further include a predetermined layer as necessary. Examples of layers provided as necessary include so-called hole transport layers and electron transport layers.
  • An example of the element structure of a photoelectric conversion element provided with one active layer is shown below.
  • Anode / active layer / cathode (2) Anode / hole transport layer / active layer / cathode (3) Anode / hole transport layer / active layer / electron transport layer / cathode (4) Anode / active layer / electron Transport layer / cathode (here, the symbol “/” indicates that the layers sandwiching the symbol “/” are stacked adjacent to each other. The same applies hereinafter).
  • the photoelectric conversion element may include two or more active layers. In this case, an intermediate electrode layer is usually provided between the active layer and the active layer.
  • An example of an element structure of a photoelectric conversion element including two active layers is shown below.
  • (layer structural unit A) is any one of the structures (1) to (4) above. In other words, it means a laminate sandwiched between an anode and a cathode. Note that the layer configuration of the two (layer structural unit A) may be different from each other.
  • (layer structural unit B) means “(layer structural unit A) / intermediate electrode layer” and symbol “x” Represents an integer of 2 or more
  • (layer structural unit B) x represents a laminate in which the layer structural unit B is laminated in x stages. Further, a plurality of (layer structural units B) may have different layer configurations.
  • an organic layer a layer containing an organic substance is referred to as an organic layer.
  • the photoelectric conversion element includes a plurality of organic layers, at least one of them is formed by the organic layer forming step of the present invention. That is, an ink containing a material that becomes the organic layer is applied to a transfer body provided with a member made of silicone rubber on the surface portion, an ink film is formed on the transfer body, and the ink film of the transfer body is formed. Is transferred to the substrate to form an organic layer.
  • the specific aspect of the organic layer forming step of the present invention is not particularly limited as long as the organic layer forming step is performed by a printing method using a transfer body in which a member made of silicone rubber is provided on the surface portion.
  • the organic layer forming step is performed using, for example, a printing apparatus such as a reverse printing apparatus or a relief printing apparatus described below.
  • FIG. 1 is a schematic diagram of a printing apparatus.
  • FIG. 2 is a schematic cross-sectional view of the blanket cylinder and the coating unit.
  • the printing apparatus 5 is an apparatus for forming an organic layer 73 on a substrate 60.
  • the printing apparatus 5 includes a gantry 1, a blanket cylinder 11, a blanket 10 that is wound around the blanket cylinder 11, and a coating unit 20 that applies ink 28 to the blanket 10 and applies an ink film 70.
  • a drying device 30 that dries the coated ink film 70 to form a dried ink film 71, a plate 50 used for patterning by removing a predetermined portion from the dried ink film 71, and A platen platen 51 that supports the plate 50, a substrate platen 61 that supports a substrate 60 on which the patterned ink film is to be transferred, and the blanket cylinder 11 are supported on the gantry 1 and the blanket cylinder 11 is disposed in the horizontal direction. And a blanket cylinder support portion 40 that moves to the center.
  • the coating unit 20, the platen surface plate 51, and the substrate surface plate 61 are arranged in a line in this order on the top of the gantry 1 (from right to left in FIG. 1).
  • the coating unit 20, the plate surface plate 51, and the substrate surface plate 61 are fixed to the gantry 1, and the blanket cylinder support unit 40 and the blanket cylinder 11 supported by the same are moved in the horizontal direction.
  • the coating unit 20, the plate surface plate 51, and the substrate surface plate 61 move in the horizontal direction, and the blanket cylinder support portion 40 and the blanket cylinder 11 supported thereby are fixed to the gantry 1. May be.
  • the blanket cylinder 11 included in the printing apparatus 5 and the blanket 10 wound around the blanket cylinder 11 correspond to a transfer body in which a member made of silicone rubber is provided on the surface portion.
  • the blanket 10 included in the printing apparatus 5 corresponds to a member made of silicone rubber provided on the surface portion of the transfer body.
  • the blanket cylinder 11 has a cylindrical shape, and the central shaft 12 is rotatably supported by the blanket cylinder support portion 40. As a result, the blanket cylinder 11 can rotate about the horizontal axis (center axis 12) (in the direction of the white arrow in FIG. 2).
  • the blanket 10 is wound around the circumferential surface of the blanket cylinder 11.
  • the blanket 10 has a flat peripheral surface and has a predetermined elasticity.
  • the blanket 10 can be formed using any kind of silicone rubber, such as thermosetting millable silicone rubber, addition-type liquid silicone rubber, and condensation-type liquid silicone rubber.
  • thermosetting millable silicone rubber examples include “KE555U” manufactured by Shin-Etsu Chemical Co., Ltd.
  • Examples of the addition type liquid silicone rubber include KE1600 and KE1606 manufactured by Shin-Etsu Chemical Co., Ltd.
  • condensation type liquid silicone rubber examples include KE-17 manufactured by Shin-Etsu Chemical Co., Ltd.
  • SIM-260 and SIM-360 manufactured by Shin-Etsu Chemical Co., Ltd. can also be used.
  • the peripheral surface of the blanket 10 is subjected to water repellent treatment.
  • the blanket cylinder support unit 40 supports the blanket cylinder 11 so as to be rotatable about the horizontal axis on the gantry 1 and moves the blanket cylinder 11 in the horizontal direction (left and right direction in FIG. 1). Specifically, the blanket cylinder support unit 40 in FIG. 1 moves the blanket cylinder 11 from above the coating unit 20 to the left to move above the plate 50 and further to the left, thereby moving the substrate 60. Can be passed above. At the time of this movement, the blanket 10 is brought into contact with the surface of the plate 50 with a predetermined pressure to roll the blanket 10, and the blanket 10 is brought into contact with the surface of the substrate 60 with a predetermined pressure. The blanket cylinder 11 can reach the left end of the substrate 60 by rolling. Thereafter, the blanket cylinder 11 can be moved again above the coating unit 20. Moreover, this blanket cylinder support part 40 can rotate the blanket cylinder 11 at a predetermined speed.
  • the plate 50 is fixed and supported on a plate surface plate 51.
  • the plate 50 is made of, for example, glass or metal. Concavities and convexities are formed on the surface portion of the plate 50.
  • the uneven pattern is formed so as to correspond to the pattern of the organic layer 73 to be formed.
  • the shape and size of the recess (pattern) of the organic layer 73 when viewed from one side in the thickness direction of the substrate 60 depends on the pattern of the organic layer 73, but is rectangular, for example. In this case, it is 20 ⁇ m ⁇ 200 mm to 50 mm ⁇ 200 mm.
  • the type of the coating unit 20 for applying and forming the ink 28 containing the material of the organic layer 73 on the transfer body is not particularly limited.
  • an anilox roll may be used as the coating unit 20, and a nozzle having a slit-like discharge port may be used.
  • FIG. 2 shows a coating unit 20 having a nozzle having a slit-like discharge port as an example of the coating unit.
  • the coating unit 20 shown in FIG. 2 includes a coating die 21, an ink tank 22, a line 23 that connects the ink tank 22 and the coating die 21, a coating die lifting unit 24 that lifts and lowers the coating die 21, and an ink.
  • An ink tank raising / lowering unit 25 for raising and lowering the tank 22 is provided.
  • the coating die 21 is a so-called capillary coater having a capillary passage 21a.
  • One end 21 b of the capillary passage 21 a of the coating die 21 communicates with the ink tank 22 through a line 23.
  • the ink 28 supplied from the ink tank 22 is supplied to the capillary passage 21a through the line 23, and is further discharged upward from the elongated rectangular slit 21c which is the other end of the capillary passage 21a.
  • the coating die 21 is arranged so that the length direction of the slit 21 c is parallel to the central axis 12 of the blanket cylinder 11.
  • the width of the slit 21c is not particularly limited.
  • the width of the slit 21c is preferably about 0.05 mm to 0.5 mm.
  • the coating unit 20 is not limited to a configuration having a capillary coater like the coating die 21 shown in FIG.
  • the coater provided in the coating unit 20 may be any coater that can coat the blanket 10 with the ink film 70 having a relatively uniform thickness.
  • a wire bar coater, a slit coater, a die coater, or the like may be used.
  • these coaters since the uniformity of the ink film 70 can be improved, a die coater, a capillary coater, and a slit coater are preferable.
  • the ink 28 is discharged from the slit 21c and the blanket cylinder 11 is rotated (in the direction of the white arrow in FIG. 2).
  • the blanket cylinder 11 is rotated (in the direction of the white arrow in FIG. 2).
  • an ink film 70 having a certain thickness is applied to the surface of the blanket 10.
  • the ink tank 22 is a tank that stores the ink 28.
  • This ink 28 is an ink used for forming an organic layer such as an active layer and a charge transport layer on the substrate 60.
  • the ink tank lifting / lowering unit 25 moves the ink tank 22 in the vertical direction (the vertical direction in FIGS. 1 and 2).
  • the coating die lifting / lowering unit 24 moves the coating die 21 in the vertical direction (the vertical direction in FIGS. 1 and 2).
  • the discharge speed of the ink 28 discharged from the slit 21c can be controlled by adjusting the relative position of the ink tank 22 and the blanket 10 in the vertical direction. Further, the thickness of the ink film 70 applied to the blanket 10 can be controlled by adjusting the discharge speed of the ink 28 from the slit 21 c and the rotation speed of the blanket cylinder 11. The thickness of the ink film 70 can be set to 2 ⁇ m to 20 ⁇ m, for example.
  • the ink film formed on the blanket it is preferable to dry the ink film formed on the blanket.
  • the method for drying the ink film is not particularly limited, but in the present embodiment shown in FIG. 2, the ink film 70 is dried by the drying device 30 to obtain the dried ink film 71.
  • the drying device 30 can dry the ink film 70 applied to the blanket 10 by spraying a gas 8 having a flow rate of 1 ⁇ 10 4 L / min ⁇ m 2 to 50 ⁇ 10 4 L / min ⁇ m 2.
  • the gas 8 sprayed from the drying device 30 onto the ink film 70 can be heated from room temperature to 40 ° C., for example. However, if the temperature of the gas 8 is too high, the temperature of the device rises and adversely affects the transfer accuracy. There is a fear. Therefore, the temperature of the gas 8 is preferably room temperature.
  • the flow rate of the gas 8 is preferably 5 ⁇ 10 4 L / min ⁇ m 2 to 20 ⁇ 10 4 L / min ⁇ m 2 .
  • the gas 8 include air, nitrogen, oxygen and the like.
  • the gas 8 is preferably air.
  • the example in which the gas 8 is sprayed on the ink film 70 in order to make the ink film 70 the dried ink film 71 has been described.
  • the ink film 70 formed by coating may be naturally dried for a certain period of time to form a dried ink film 71 and then transferred to the substrate 60.
  • the natural drying time is, for example, 10 seconds to 120 seconds.
  • an ink containing a material that becomes the organic layer is applied to a transfer body provided with a member made of silicone rubber on the surface portion, and an ink film is formed on the transfer body. And the ink film is transferred to the substrate to form the organic layer.
  • the blanket 10 made of silicone rubber by using the blanket 10 made of silicone rubber, it is possible to remove substantially all portions of the dried ink film 71 to be removed. Also, when the dried ink film 71 is transferred to the substrate 60, substantially all the dried ink film 71 is transferred to the substrate 60. Since the dried ink film 71 is transferred to the substrate 60 substantially without crying, the organic layer 73 having a flat surface can be formed.
  • the ink film 70 on the transfer body is preferably dried under predetermined conditions. That is, when a predetermined portion of the ink film 70 on the transfer body is removed by bringing the blanket 10 into contact with the surface of the plate 50 with a predetermined pressure, the portion to be removed of the ink film 70 is transferred to the transfer body. It is preferable to dry to such an extent that substantially all can be removed. Further, when transferring the ink film to the substrate 60, it is preferable to dry the ink film to such an extent that substantially all the ink film is transferred from the transfer body.
  • the reverse printing method in which the ink film 70 is transferred to the substrate 60 using the reverse printing device as the printing device 5 has been described.
  • the relief printing apparatus used in the relief printing method removes the plate 50 and the plate surface plate 51 from the printing apparatus 5 shown in FIG. 1, for example, and replaces the blanket 10 with a flat surface wound around the blanket cylinder 11.
  • a configuration using a letterpress wound around the blanket cylinder 11 may be used.
  • the letterpress wound around the blanket cylinder in the letterpress printing apparatus can be formed of, for example, the same material as the blanket 10 of the printing apparatus 5 already described.
  • the relief printing plate can form a plurality of projections by pouring a silicone rubber material into a mold on which a predetermined pattern is formed and curing the material.
  • the shape and size of each convex portion in plan view depends on the pattern of the organic layer formed on the substrate, but is 20 ⁇ m ⁇ 200 mm to 50 mm ⁇ 200 mm in the case of a rectangular shape, for example.
  • a stripe-shaped convex part may be formed by arranging these rectangular convex parts in parallel in a plan view. For example, 10 to 100 convex portions are arranged.
  • substantially all of the ink film is transferred to the substrate when the ink film is transferred to the substrate. Therefore, substantially all the ink film is transferred to the substrate without causing the ink film to cry, so that an organic layer having a flat surface can be formed.
  • the ink 28 used in the coating unit 20 contains the material of the organic layer 73 to be formed and a solvent. After forming the ink film 70 having a predetermined pattern, the organic layer 73 can be formed by drying.
  • the viscosity of the ink 28 supplied to the transfer body is preferably 2 mPa ⁇ s to 50 mPa ⁇ s, and the yield value is preferably 10 mPa or less.
  • the viscosity of the ink 28 within this range, the ink film on the transfer body can be sufficiently flattened by the surface tension of the ink 28 and the uniformity of the thickness of the ink film can be made extremely high. . If the viscosity and yield value of the ink 28 exceed the above ranges, it tends to be difficult to sufficiently increase the uniformity of the thickness of the ink film on the transfer body before the ink film is dried and solidified.
  • the ink 28 is obtained by dissolving or dispersing the material to be the organic layer 73 in a solvent, and the solvent is not particularly limited as long as the material to be the organic layer 73 is dissolved or dispersed.
  • solvents include monochlorobenzene, p-dichlorobenzene, o-dichlorobenzene, chloroform, toluene, xylene, tetralin; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether.
  • Ethylene glycol monoalkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dialkyl ethers such as diethylene glycol dibutyl ether; ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; Alkylene glycol alkyl ether acetates such as methyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate and methoxypentyl acetate; aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene; anisole Aromatic ketones such as phenetole and methylanisole; ketones such as acetone, 2-butanone, 2-heptanone, 3-heptanone
  • the content of the solvent in the ink 28 is usually 50% by mass or more and 99% by mass or less, and preferably 80% by mass or more and 98% by mass or less, by mass fraction.
  • the ink 28 may further contain other additives.
  • the additive include a filler, a polymer compound other than the binder polymer, a surfactant, an adhesion promoter, an aggregation inhibitor, an organic acid, and a curing agent.
  • surfactant examples include nonionic surfactants, cationic surfactants, anionic surfactants, and amphoteric surfactants.
  • a substrate provided with one of the pair of electrodes is prepared.
  • a substrate on which one electrode is provided in advance may be obtained from the market, or one electrode of a pair of electrodes may be formed on the substrate in this step.
  • a predetermined inorganic layer may be formed on one of the pair of electrodes as necessary after the substrate preparation step.
  • Organic layer formation process In this step, an organic layer is formed. This step is performed at least once, but is performed a plurality of times as necessary.
  • the organic layer forming step of the present invention When a plurality of organic layers are provided between a pair of electrodes, at least one of the organic layers is formed by the organic layer forming step of the present invention. That is, an ink containing a material that becomes the organic layer is applied to a transfer body provided with a member made of silicone rubber on the surface, and an ink film is formed on the transfer body, and the ink film is applied to the substrate. By transferring and forming the organic layer, at least one organic layer is formed.
  • This step is performed using, for example, the above-described reverse printing apparatus and letterpress printing apparatus.
  • another organic layer may be formed by a method other than the organic layer forming step of the present invention.
  • Another organic layer may be formed by coating by a printing method, an offset printing method, an ink jet printing method, a dispenser printing method, a nozzle coating method, a capillary coating method, or the like.
  • a step of forming the inorganic layer is performed between the organic layer forming step and the organic layer forming step.
  • the other electrode forming step In this step, the other electrode of the pair of electrodes is formed. Thereby, a photoelectric conversion element is produced.
  • the organic layer forming step described above it is preferable to dry the ink film on the transfer body.
  • Ink for forming a plurality of organic layers by a coating method wherein the organic layer formed earlier forms a subsequent organic layer in the step of forming another organic layer on the predetermined organic layer
  • the function of the previously formed organic layer may be impaired.
  • the composition which comprises the organic layer formed previously may mix in the organic layer formed later, and the function of the organic layer formed later may be impaired.
  • the ink film dried to some extent is laminated on the substrate, it is possible to prevent the previously formed organic layer from being redissolved in the ink for forming the subsequent organic layer.
  • the plurality of organic layers can be stacked as intended without impairing the functions of the plurality of organic layers.
  • the active layer has a single layer structure and a multi-layer structure in which a plurality of thin films are stacked.
  • the active layer of 1 layer structure can be formed by performing the above-mentioned organic layer formation process once.
  • an active layer having a multi-layer structure can be formed by repeating the organic layer forming step by the number of layers. For example, one of a thin film containing an electron donating compound material and a thin film containing an electron accepting compound material, which will be described later, is formed in the organic layer forming step, followed by the thin film containing the electron donating compound material and the electron accepting material.
  • An active layer having a multilayer structure can be formed by forming the other thin film among the thin films containing the organic compound material in a separate organic layer forming step.
  • each layer can be laminated
  • a photoelectric conversion element including a plurality of active layers can also be produced.
  • a configuration example of a photoelectric conversion element including a plurality of active layers is as follows.
  • Photoelectric conversion element comprising two active layers (5) Anode / (layer structural unit A) / intermediate electrode layer / (layer structural unit A) / cathode Photoelectric conversion element comprising three or more active layers (6) Anode / (Layer structural unit B) x / (Layer structural unit A) / Cathode
  • two or more active layers are formed in the organic layer forming step already described, and between each step of forming two or more photoelectric active layers. It can be produced by forming an intermediate electrode layer.
  • an intermediate electrode layer is formed by a coating method, as in the organic layer forming step already described, an ink containing a material that becomes the intermediate electrode layer is formed on a transfer body provided with a member made of silicone rubber on the surface portion. May be applied to form an ink film on the transfer body, and the ink film may be transferred to the substrate to form an intermediate electrode layer.
  • the photoelectric conversion element of the present invention is usually formed on a substrate.
  • the substrate may be any substrate that does not change chemically when the photoelectric conversion element is formed.
  • Examples of the material for the substrate include glass, plastic, polymer film, and silicon.
  • a substrate that exhibits light transmittance is used.
  • a pair of electrodes Since a photoelectric conversion element needs to take in light inside, at least one of a pair of electrodes needs to be comprised by the electrode which shows a light transmittance.
  • Examples of the electrode exhibiting light transmittance include a conductive metal oxide film and a translucent metal thin film.
  • the electrode exhibiting light transmittance is formed using a conductive material such as indium oxide, zinc oxide, tin oxide, indium tin oxide (ITO), indium zinc oxide (IZO), NESA, gold, platinum, silver, copper, and the like.
  • a film made of ITO, IZO, or tin oxide is preferable.
  • Examples of the electrode manufacturing method include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like.
  • the electrode material include metals such as lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and the like.
  • Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, calcium-aluminum alloy and the like.
  • Predetermined layers other than the active layer are provided as predetermined layers in order to improve photoelectric conversion efficiency.
  • the material of these predetermined layers include alkali metal such as lithium fluoride, halide or oxide of alkaline earth metal, fine particles of inorganic semiconductor such as titanium oxide, PEDOT (poly-3,4-ethylenedioxide). Oxythiophene) and the like.
  • the active layer contains an electron donating compound and an electron accepting compound, and further contains an ultraviolet absorber, inorganic semiconductor fine particles, an antioxidant for the ultraviolet absorber, and the like as necessary.
  • the electron donating compound and the electron accepting compound are relatively determined from the energy level of the energy level of these compounds.
  • the active layer has a single layer structure and a multi-layer structure in which a plurality of thin films are stacked.
  • the active layer having a single layer structure contains an electron donating compound and an electron accepting compound in one active layer.
  • the active layer having a multilayer structure is formed by laminating, for example, a thin film containing an electron donating compound material and a thin film containing an electron accepting compound material.
  • the photoelectric conversion element has a plurality of active layers, it is preferable that the photoelectric conversion elements have active layers having different light absorption regions.
  • Electrode donating compound p-type semiconductor polymer
  • the electron donating compound include pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, oligothiophene and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, and aromatic amines in side chains or main chains.
  • p-type semiconductor polymers such as polysiloxane derivatives, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, polyphenylene vinylene and derivatives thereof, and polythienylene vinylene and derivatives thereof.
  • an organic polymer compound having at least one structural unit of a structural unit represented by the following formula (1) and a structural unit represented by the following formula (2): Can be mentioned.
  • Ar 1 and Ar 2 each independently represent a trivalent heterocyclic group.
  • R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, aryl Alkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imino group, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group It represents a monovalent heterocyclic group, heterocyclic oxy group, heterocyclic thio group, arylalkenyl group, arylalkynyl group, carboxyl group or cyano group.
  • R 50 is a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide Group, acid imide group, imino group, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent heterocyclic group, heterocyclic oxy group, heterocyclic thio group, aryl An alkenyl group, an arylalkynyl group, a carboxyl group or a cyano group is represented.
  • R 51 is an alkyl group having 6 to 20 carbon atoms, an alkyloxy group having 6 to 20 carbon atoms, an alkylthio group having 6 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, or 6 to 6 carbon atoms.
  • An acyl group having 6 to 60 carbon atoms or an acyloxy group having 6 to 60 carbon atoms is represented.
  • X 1 and Ar 2 are bonded to the adjacent position of the heterocyclic ring contained in Ar 1
  • C (R 50 ) (R 51 ) and Ar 1 are bonded to the adjacent position of the heterocyclic ring contained in Ar 2. ing.
  • organic polymer compound a compound containing both the structural unit represented by the formula (1) and the structural unit represented by the formula (2) is more preferable.
  • suitable p-type semiconductor polymers include organic polymer compounds containing an arylene group as a structural unit from the viewpoint of solubility in an organic solvent and ease of raising the degree of polymerization.
  • the arylene group is an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon, and a group having a condensed ring, two or more independent benzene rings or condensed rings are directly or via a group such as vinylene. Group bonded together.
  • the arylene group may have a substituent.
  • the substituent include linear or branched alkyl groups having 1 to 20 carbon atoms or cycloalkyl groups having 1 to 20 carbon atoms, linear or branched groups having 1 to 20 carbon atoms. Examples thereof include an alkoxy group having an alkyl group or a cycloalkyl group having 1 to 20 carbon atoms in its structure.
  • the number of carbon atoms in the arylene group excluding the substituent is usually about 6 to 60, and preferably 6 to 20.
  • the total number of carbon atoms including the substituent of the arylene group is usually about 6 to 100.
  • arylene groups include phenylene groups, naphthalenediyl groups, anthracene-diyl groups, biphenyl-diyl groups, terphenyl-diyl groups, fluorenediyl groups (preferably 9,9'-dialkyl-fluorene-2,7- A diyl group), a benzofluorenediyl group, and the like.
  • the organic polymer compound containing the arylene group as a structural unit is preferably a copolymer further containing a structural unit other than the arylene group.
  • Examples of the structural unit other than the arylene group include a structural unit that is a thienylene group that may have a substituent (preferably a 2,5-thienylene group that may have a substituent), in the above formula (1).
  • the structural unit represented and the structural unit which combined these are mentioned.
  • Examples of the substituent that the thienylene group may have include a linear or branched alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 1 to 20 carbon atoms.
  • As the compound containing the arylene group as a structural unit for example, polymer compound A represented by the following formula (3) and polymer compound B represented by the following formula (4) are used.
  • Electrode-accepting compound n-type semiconductor such as n-type semiconductor polymer
  • the electron-accepting compound include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and metal complexes of derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene and derivatives thereof, fullerenes and derivatives thereof such as C 60 fullerene, bathocuproine And phenanthrene derivatives such as titanium oxide, metal oxides such as titanium oxide, and carbon nanotubes.
  • titanium oxide, carbon nanotubes, fullerenes titanium oxide, carbon nanotubes, fuller
  • fullerene examples include C 60 fullerene, C 70 fullerene, C 76 fullerene, C 78 fullerene, such as C 84 fullerene, and the like.
  • fullerene and fullerene derivatives include C 60 fullerene, C 70 fullerene, C 76 fullerene, C 78 fullerene, C 84 fullerene and derivatives thereof.
  • Specific examples of the fullerene derivative include the following compounds.
  • fullerene derivatives include [6,6] phenyl-C 61 butyric acid methyl ester (C 60 PCBM, [6,6] -Phenyl C 61 butyric acid methyl ester), and [6,6] phenyl-C 71.
  • Butyric acid methyl ester (C 70 PCBM, [6,6] -Phenyl C 71 butyric acid methyl ester), [6,6] Phenyl-C 85 butyric acid methyl ester (C 84 PCBM, [6,6] -Phenyl C 85 butyric acid methyl ester), [6,6] thienyl -C 61 butyric acid methyl ester ([6,6] -Thienyl C 61 butyric acid methyl ester) and the like.
  • the ratio of the fullerene derivative is preferably 10 parts by weight to 1000 parts by weight and preferably 20 parts by weight to 500 parts by weight with respect to 100 parts by weight of the electron donating compound. It is more preferable.
  • the thickness of the active layer is usually preferably 1 nm to 100 ⁇ m, more preferably 2 nm to 1000 nm, still more preferably 5 nm to 500 nm, more preferably 20 nm to 200 nm.
  • the active layer may contain other components as necessary.
  • other components include ultraviolet absorbers, antioxidants, sensitizers for sensitizing the function of generating charges by absorbed light, and light stabilizers for increasing stability from ultraviolet rays. .
  • Components other than the electron donating compound and the electron accepting compound constituting the active layer are each usually 5 parts by weight or less with respect to 100 parts by weight of the total amount of the electron donating compound and the electron accepting compound, and 0.01 wt. It is effective to blend in an amount of from 3 to 3 parts by weight.
  • the active layer may contain a polymer compound other than the electron donating compound and the electron accepting compound of the present invention as a polymer binder in order to enhance mechanical properties.
  • a polymer binder those that do not inhibit the electron transport property or hole transport property are preferable, and those that do not strongly absorb visible light are preferably used.
  • polymer binder examples include poly (N-vinylcarbazole), polyaniline and its derivatives, polythiophene and its derivatives, poly (p-phenylene vinylene) and its derivatives, poly (2,5-thienylene vinylene) and its Derivatives, polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like can be mentioned.
  • an intermediate electrode layer is provided between the active layers as necessary.
  • the material for the intermediate electrode layer metals such as gold, platinum, chromium, nickel, lithium, magnesium, calcium, tin, silver, and aluminum are used.
  • the intermediate electrode layer may be composed of metal particles having an average particle diameter of 50 nm or less.
  • the intermediate electrode layer preferably has a high light transmittance so that the plurality of active layers can absorb light.
  • the intermediate electrode layer can be formed by a method of coating a film in which metal particles are dispersed or a vacuum deposition method.
  • the intermediate electrode layer can also be formed by a printing method similar to the organic layer forming step as described above.
  • the photoelectric conversion element of the present invention can be operated as an organic thin film solar cell by generating a photoelectromotive force between the electrodes by irradiating light such as sunlight from an electrode exhibiting optical transparency. It can also be used as an organic thin film solar cell module by integrating a plurality of organic thin film solar cells.
  • the organic thin film solar cell module can basically have the same module structure as a conventional solar cell module.
  • the organic thin film solar cell module generally has a structure in which cells are formed on a support substrate such as metal or ceramic, the cell is covered with a filling resin, protective glass, or the like, and light is taken in from the opposite side of the support substrate.
  • the organic thin film solar cell module may have a structure in which cells are formed on a transparent support substrate using a transparent material such as tempered glass and light is taken in from the transparent support substrate side.
  • a module structure called a super straight type, a substrate type, or a potting type, a substrate integrated module structure used in an amorphous silicon solar cell, or the like is known. Even in the organic thin film solar cell module to which the photoelectric conversion element of the present invention is applied, these module structures can be appropriately selected in consideration of the purpose of use, the place of use and the environment of use.
  • cells are arranged at regular intervals between support substrates that are transparent on one or both sides and subjected to antireflection treatment, and adjacent cells are metal leads or It is connected by flexible wiring or the like, and a collecting electrode is arranged on the outer edge portion, so that the generated power is taken out to the outside.
  • plastic materials such as ethylene vinyl acetate (EVA) may be used between the substrate and the cell in the form of a film or a filled resin in order to protect the cell and improve current collection efficiency.
  • EVA ethylene vinyl acetate
  • the surface protective layer is made of a transparent plastic film or the above filling resin is cured.
  • the periphery of the support substrate is fixed in a sandwich shape with a metal frame in order to ensure internal sealing and module rigidity, and the support substrate and the frame are hermetically sealed with a sealing material.
  • a flexible material is used for the cell itself, the support substrate, the filling material, and the sealing material, a solar cell can be formed on the curved surface.
  • a solar cell using a flexible support such as a polymer film
  • cells are sequentially formed while feeding out a roll-shaped support, cut to a desired size, and then the periphery is sealed with a flexible and moisture-proof material.
  • the battery body can be produced.
  • it can also have a module structure called “SCAF” described in Solar Energy Materials and Solar Cells, 48, p383-391.
  • SCAF solar Energy Materials and Solar Cells, 48, p383-391.
  • a solar cell using a flexible support can be used by being bonded and fixed to a curved glass or the like.
  • the photoelectric conversion element of the present invention can be operated as an organic photosensor by irradiating light from a transparent or translucent electrode in a state where a voltage is applied between the electrodes, so that a photocurrent flows. Furthermore, the organic photosensor is used as a light receiving unit, a drive circuit unit that detects an output due to a signal current generated by the organic photosensor and reads the signal charge, and a wiring that connects the organic photosensor and the drive circuit are provided. It can be used as an organic image sensor.
  • the organic light sensor can be used with a color filter on the light incident surface side to provide color selectivity of light to be detected, or light absorption with high selectivity for each of the three primary colors of light.
  • a plurality of types of organic photosensors having characteristics can also be used.
  • the driving circuit an IC chip formed of a transistor using single crystal silicon, or a thin film transistor using a compound semiconductor such as polycrystalline silicon, amorphous silicon, or cadmium selenide, and a conjugated organic compound semiconductor such as pentacene.
  • the organic image sensor has a lower manufacturing cost than an existing image sensor using a charge coupled device (CCD) or a complementary metal oxide semiconductor (CMOS) as an imaging element for a scanner, digital camera, digital video, etc. Advantages such as a small installation area can be expected.
  • organic photosensors having various photosensitivity characteristics can be used due to the diversity of conjugated compounds. Therefore, it is possible to provide an organic image sensor having performance according to the application.
  • Dichlorobis (triphenylphosphine) palladium (II) (0.02 g) was added, the temperature was raised to 105 ° C., and 42.2 mL of a 2 mol / L sodium carbonate aqueous solution was added dropwise with stirring. After completion of the dropwise addition, the mixture was reacted for 5 hours, phenylboronic acid (2.6 g) and 1.8 mL of toluene were added, and the mixture was stirred at 105 ° C. for 16 hours. Thereafter, 700 mL of toluene and 200 mL of an aqueous 7.5% sodium diethyldithiocarbamate trihydrate solution were added, and the mixture was stirred at 85 ° C.
  • the organic layer was washed twice with 300 mL of ion exchanged water at 60 ° C., once with 300 mL of 3% acetic acid at 60 ° C., and further washed with 300 mL of ion exchanged water at 60 ° C. three times.
  • the organic layer was passed through a column filled with celite, alumina, and silica, and the column was washed with 800 mL of hot toluene.
  • the solution was concentrated to 700 mL, poured into 2 L of methanol, and reprecipitated.
  • the polymer was recovered by filtration and washed with 500 mL of methanol, acetone, and methanol.
  • OPV ink (ink for active layer)
  • the polymer A as an electron donating compound and PCBM as an electron accepting compound were dissolved in orthodichlorobenzene to prepare an OPV ink.
  • the concentration of polymer A in the OPV ink was 0.5% by weight, and the concentration of PCBM in the OPV ink was 1.5% by weight.
  • the viscosity of the OPV ink was 12 cP and the yield value was 1.37 dyn / cm 2 .
  • a blanket made of silicone rubber having a flat surface was prepared, and a predetermined surface portion of this blanket was cut out to form a plurality of convex portions on the surface portion of the blanket, thereby producing a relief plate.
  • the shape of the convex part in plan view is a rectangle, and the dimension is 10 mm ⁇ 180 mm.
  • the produced relief was wound around a blanket cylinder to obtain a transfer body.
  • OPV ink was applied to the relief plate with a CAP coater (capillary coater) to form an ink film on the surface of the projection. Thereafter, the ink film was naturally dried for 60 seconds.
  • CAP coater capillary coater
  • a PET (Polyethylene terephthalate) film was set on the substrate platen, the blanket cylinder was rotated by moving the substrate platen while the relief plate was pressed against the PET film, and the ink film on the relief plate was transferred to the PET film.
  • the letterpress was visually confirmed. As a result, substantially all of the ink film was transferred from the letterpress to the PET film, and no ink film remained on the letterpress.
  • the active layer formed on the PET film had a thickness of 170 nm ⁇ 5 nm. As a result, an organic layer (active layer) excellent in flatness was formed.

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  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Photovoltaic Devices (AREA)

Abstract

L'invention concerne un procédé de production d'éléments de conversion photoélectrique pouvant former une couche organique plate, par la mise mise en oeuvre d'un procédé d'impression. Ce procédé de production permet de produire des éléments de conversion photoélectrique comprenant deux électrodes et au moins une couche organique (73) disposée entre les deux électrodes. Ce procédé consiste : à préparer un substrat (60) sur lequel est disposé une des électrodes ; à appliquer de l'encre contenant le matériau pour les couches organiques sur un corps de transfert (10) pourvu d'un élément comportant du caoutchouc de silicone sur une partie de surface, de sorte à former des films d'encre (70,71) sur le corps de transfert, ces films d'encre étant ensuite transférés sur le substrat pour former les couches organiques ; et à former l'électrode restante.
PCT/JP2011/073388 2010-10-19 2011-10-12 Procédé de production d'éléments de conversion photoélectrique WO2012053400A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007095343A (ja) * 2005-09-27 2007-04-12 Toppan Printing Co Ltd 印刷物の製造方法および印刷物
WO2008078699A1 (fr) * 2006-12-26 2008-07-03 Asahi Kasei E-Materials Corporation Composition de résine pour une plaque d'impression
JP2009206273A (ja) * 2008-02-27 2009-09-10 National Institute Of Advanced Industrial & Technology 積層型有機太陽電池
WO2010113931A1 (fr) * 2009-03-31 2010-10-07 Dic株式会社 Composition d'encre semi-conductrice organique et procédé de formation d'un motif semi-conducteur organique au moyen de celle-ci

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007095343A (ja) * 2005-09-27 2007-04-12 Toppan Printing Co Ltd 印刷物の製造方法および印刷物
WO2008078699A1 (fr) * 2006-12-26 2008-07-03 Asahi Kasei E-Materials Corporation Composition de résine pour une plaque d'impression
JP2009206273A (ja) * 2008-02-27 2009-09-10 National Institute Of Advanced Industrial & Technology 積層型有機太陽電池
WO2010113931A1 (fr) * 2009-03-31 2010-10-07 Dic株式会社 Composition d'encre semi-conductrice organique et procédé de formation d'un motif semi-conducteur organique au moyen de celle-ci

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