WO2017069546A1 - Composition permettant une réduction d'une fonction de travail d'une couche collectrice d'électrons en oxyde métallique, cellule solaire organique inversée utilisant ladite composition, et procédé de préparation d'une cellule solaire organique inversée - Google Patents

Composition permettant une réduction d'une fonction de travail d'une couche collectrice d'électrons en oxyde métallique, cellule solaire organique inversée utilisant ladite composition, et procédé de préparation d'une cellule solaire organique inversée Download PDF

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WO2017069546A1
WO2017069546A1 PCT/KR2016/011865 KR2016011865W WO2017069546A1 WO 2017069546 A1 WO2017069546 A1 WO 2017069546A1 KR 2016011865 W KR2016011865 W KR 2016011865W WO 2017069546 A1 WO2017069546 A1 WO 2017069546A1
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oxide
layer
work function
solar cell
organic solar
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English (en)
Korean (ko)
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김영규
김화정
남성호
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경북대학교 산학협력단
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L31/0248—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies
    • H01L31/0256—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by the material
    • 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
    • H10K30/50—Photovoltaic [PV] devices
    • 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
    • H10K30/80—Constructional details
    • H10K30/84—Layers having high charge carrier mobility
    • H10K30/86—Layers having high hole mobility, e.g. hole-transporting layers or electron-blocking layers
    • 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

Definitions

  • the present invention relates to a composition for reducing work function of a metal oxide electron collecting layer, an inverse structure organic solar cell using the same, and a method of manufacturing the inverse structure organic solar cell.
  • Solar cells include solar cells that generate steam required to rotate turbines using solar heat, and solar cells that convert photons into electrical energy using the properties of semiconductors. Refers to an optical cell.
  • the organic solar cell can be made into a thin film with a thickness of several hundred nm and can be applied to a flexible structure, which is expected to be applied to various applications such as presenting the potential as an energy source of the future mobile information system. .
  • a general organic solar cell includes a lower electrode layer formed on a substrate, a hole transport layer formed in contact with the surface of the lower electrode layer, at least one active layer formed in contact with the surface of the hole transport layer, and an upper electrode layer formed on the active layer. do.
  • positive charges holes
  • negative charges electrons are moved to the electrode on the active layer, and holes are moved to the hole transport layer.
  • the active layer of the conventional organic solar cell is an electron donor material poly (3-hexylthiophene) (hereinafter referred to as P3HT) and an electron acceptor material 1- (3-methoxycarbonyl) -propyl- It is prepared using a mixture of 1-phenyl- (6,6) C 61 (1- (3-methoxycarbonyl) -propyl-1-phenyl- (6,6) C 61 , hereinafter PCBM).
  • an organic solar cell having an inverse structure is stable in air while utilizing metal oxides such as TiO 2 and ZnO to solve the problem. And, it is emerging as the most representative method that can be applied to the roll-to-roll process.
  • Inversely structured organic solar cells contain electrons from transparent electrodes (e.g., ITO or FTO) in contrast to the collection of holes from transparent electrodes such as indium-tin oxide (ITO) in the device structure of conventional positive structure organic solar cells.
  • transparent electrodes e.g., ITO or FTO
  • ITO indium-tin oxide
  • Collected to act as a cathode (cathode) the anode (Anode) may be used a metal such as Au, Ag.
  • the device structure of the reverse structure organic solar cell as described above may not use a metal such as Ca or Al, which is a highly reactive electron collecting electrode (cathode) used in a general positive structure organic solar cell device, and both a positive electrode and a negative electrode may be used.
  • a metal such as Ca or Al
  • cathode highly reactive electron collecting electrode
  • the high work-function allows the use of materials that are not reactive to air or moisture.
  • the 1st aspect of this invention provides the composition for reducing work function of the metal oxide electron collection layer containing the compound represented by following formula (1).
  • R is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl or C 1-6 alkoxy,
  • n is an integer of 50-10000.
  • a second aspect of the present invention includes a first electrode, a metal oxide electron collecting layer, a work function reducing layer, a photoactive layer, a hole collecting layer and a second electrode sequentially stacked on a substrate, wherein the work function reducing layer is It provides an inverse structure organic solar cell characterized in that it comprises a compound represented by the formula (1).
  • R is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl or C 1-6 alkoxy,
  • n is an integer of 50-10000.
  • a third aspect of the invention the first step of depositing a first electrode on a substrate; Stacking a metal oxide electron collecting layer on the first electrode; A third step of forming a work function reduction layer by coating a work function reduction composition of the metal oxide electron collection layer including the compound represented by Formula 1 on the metal oxide electron collecting layer; Stacking a photoactive layer on the work function reduction layer; Stacking a hole collecting layer on the photoactive layer; And a sixth step of stacking a second electrode on the hole collecting layer.
  • R is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl or C 1-6 alkoxy,
  • n is an integer of 50-10000.
  • the work function of the metal oxide electron collecting layer is lowered.
  • the efficiency of the inverse organic solar cell using the polymer is greatly improved. It was. That is, according to the present invention, when the poly (2-oxazoline) -based neutral polymer corresponding to the compound represented by Formula 1 is applied to the metal oxide electron collecting layer, the work function of the metal oxide electron collecting layer is reduced to reduce the metal oxide electron collecting layer. And the energy level between the photoactive layer and the photoactive layer were found to facilitate the transfer / collection of charge. The present invention is based on this.
  • the present invention provides a composition for reducing the work function of a metal oxide electron collecting layer comprising a compound represented by the following Chemical Formula 1.
  • R is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl or C 1-6 alkoxy,
  • n is an integer of 50-10000.
  • n when n is outside the above range, the synthesis may not be easy and the solubility may be degraded.
  • n is more preferably an integer of 100 to 6000.
  • the compound represented by Formula 1 may have a weight average molecular weight of 10000 to 500000, for example, 50000 to 100000.
  • the composition for reducing the work function of the metal oxide electron collecting layer according to the present invention may include a compound (PEOz) represented by the following formula (2).
  • n is an integer from 50 to 10000.
  • the metal oxide electron collecting layer may be used in an inverse structure organic solar cell, and in addition to this, the work function of the metal oxide electron collecting layer may be applied without limitation to an organic device.
  • the metal oxide of the metal oxide electron collecting layer to which the work function reduction composition according to the present invention is applicable is zinc oxide (ZnO), titanium oxide (TiO x , where x is 1, 2 or 3), oxidation Indium (In 2 O 3 ), tin oxide (SnO 2 ), zinc tin oxide (Zinc Tin Oxide), gallium oxide (Ga 2 O 3 ), aluminum oxide, copper oxide (Copper (II) Oxide), copper aluminum oxide ( Copper aluminum oxide, zinc rhodium oxide, indium-gallium zinc oxide (IGZO) or mixtures thereof may be used, but is not limited thereto.
  • the present invention includes a first electrode (cathode), a metal oxide electron collecting layer, a work function reduction layer, a photoactive layer, a hole collecting layer and a second electrode (anode) sequentially stacked on a substrate as shown in FIG. 1, It provides an inverse structure organic solar cell, characterized in that the work function reducing layer comprises a compound represented by the following formula (1).
  • R is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl or C 1-6 alkoxy,
  • n is an integer of 50-10000.
  • It may be prepared by a method comprising a sixth step of stacking a second electrode on the hole collecting layer.
  • R is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl or C 1-6 alkoxy,
  • n is an integer of 50-10000.
  • the compound represented by the formula (1) as a work function reducing layer to reduce the work function of the metal oxide electron collecting layer as shown in Figure 2 to control the energy structure of the overall reverse structure organic solar cell device, that is, It is possible to improve the performance of the inverse structure organic solar cell.
  • the substrate may be a light-transmitting inorganic substrate or an organic substrate, or may be a substrate in which they are stacked in the same or different types.
  • the substrate may be glass, quartz, polyethylene terephthalate (PET), polyethylene naphthelate (PEN), polyimide (PI), polycarbonate (PC), polystyrene ( polystylene (PS), polyoxyethlene (POM), acrylonitile styrene copolymer (AS resin), Triacetyl cellulose (TAC), or mixtures thereof.
  • the first electrode is preferably a light transmissive material such that light passing through the substrate reaches the photoactive layer, and may serve as a cathode that receives electrons generated in the photoactive layer and transfers the electrons to the external circuit.
  • the first electrode may be indium tin oxide (ITO), fluorinated tin oxide (FTO), indium zinc oxide (IZO), or aluminum-doped zinc oxide (Al-doped Zinc Oxide). , AZO), zinc oxide (ZnO), indium zinc oxide (IZTO), or mixtures thereof.
  • the first electrode may be formed by applying a transparent electrode material to one surface of the substrate or coating in a film form using sputtering, E-Beam, thermal evaporation, spin coating, screen printing, inkjet printing, doctor blade or gravure printing. Can be.
  • the metal oxide electron collecting layer may also be referred to as a metal oxide electron extraction layer, and may serve to receive electrons generated in the photoactive layer and transfer them to the first electrode.
  • a metal oxide electron extraction layer As the metal oxide of the metal oxide electron collecting layer, various metal oxides mentioned in the work function reduction composition according to the present invention may be used without limitation.
  • a work function reducing layer including the neutral polymer represented by Chemical Formula 1 is formed on the surface of the metal oxide electron collecting layer.
  • the work function reduction layer may be formed in a nano-dot structure. As the work function reduction layer is formed in the nano-point structure, the area with the electrode can be increased, thereby collecting a larger amount of charge.
  • the work function reduction layer may be formed by coating a solution having a concentration of 1 to 10 mg / ml of the compound represented by Chemical Formula 1 on the metal oxide electron collecting layer.
  • a solution having a concentration of 2 to 5 mg / ml of the compound represented by Formula 1 in terms of work function reduction efficiency.
  • the work function reduction layer is deposited on the metal oxide electron collecting layer through a solution process, for example, spin coating or spray coating, to form a coating layer on the surface of the metal oxide electron collecting layer and lower its work function.
  • the coating solution for forming the work function reduction layer may use an organic solvent such as methanol, chlorobenzene, chloroform or para xylene as a solvent.
  • a photoactive layer is formed on the work function reduction layer.
  • the photoactive layer may be formed by applying a mixed solution of an electron acceptor material and an electron donor material onto the work function reduction layer and then drying the solvent.
  • the coating process may use a known coating method such as spin coating, spray coating, doctor blade coating, and inkjet printing, and may be preferably performed by spin coating.
  • the electron donor material refers to a material that absorbs sunlight to form electron-hole pairs (excitons) and moves holes separated at the pn junction interface between the electron donor material and the electron acceptor material toward the anode. .
  • the electron donor material may be a conjugated polymer that can be used as a p-type semiconductor, polythiophene-based, polyfluorene-based, polyaniline-based, polycarbazole-based, polyvinylcarba It may be a sol (polyvinylcarbazole), polyphenylene (polyphenylene), polyphenylenevinylene (polyphenylenevinylene), polysilane (polysilane), polythiazole (polythiazole) or a copolymer thereof.
  • electron donor materials include PBDTTT-C-T, PTB7-Th, PBDTT-S-TT, PBDT-TS1, PBDTTT-C, and PTB7.
  • the electron acceptor material means a material that serves to move the electrons separated at the pn junction interface in the photoactive layer toward the cathode.
  • the electron acceptor material is fullerene and PC61BM ([6,6] -phenyl-C61-butyric acid methyl ester), PC 71 BM ([6,6] -phenyl- which can be used as an n-type semiconductor. C 71 -butyric acid methyl ester), PC81BM ([6,6] -phenyl-C81-butyric acid methyl ester), and fullerene derivatives such as ICBA (indene-C60 bisadduct).
  • the hole collecting layer is a p-type buffer layer that allows the holes generated in the photoactive layer to be easily transferred to the anode, also called a hole transport layer.
  • the hole collecting layer may be a conductive metal oxide, a compounded organic of poly (3,4-ethylenedioxythiophene) [PEDOT] and poly (3-styrenesulfonate) [PSS], or a mixture thereof.
  • a conductive metal oxide a compounded organic of poly (3,4-ethylenedioxythiophene) [PEDOT] and poly (3-styrenesulfonate) [PSS], or a mixture thereof.
  • the conductive metal oxide at least one of WO 3 , V 2 O 3 , MoO 3 , and the like may be used.
  • the second electrode is a layer serving as an anode that finally collects holes and delivers the holes to an external circuit.
  • the second electrode may be any one selected from metals, alloys, conductive polymers, other conductive compounds, and combinations thereof.
  • the second electrode is preferably a material having a high oxidation stability against exposure to the atmosphere.
  • a material having a high work function such as Cu, Ag, Au, W, Ni, and Ti. desirable.
  • each of the above layers may be formed by thermal image deposition, electron beam deposition, sputtering, ion plating or chemical vapor deposition, and the work function reduction layer may be formed by a solution process as described above.
  • the electrodes may be formed by applying an electrode forming paste including a metal and then heat treatment.
  • the present invention lowers the work function of the metal oxide by modifying the surface of the metal oxide electron collecting layer, which is a component of the inverse structure organic solar cell, using a neutral polymer, thereby increasing the built-in potential, and the neutral polymer.
  • the efficiency of the inverse organic solar cell using the polymer can be greatly improved.
  • it is expected to accelerate the commercialization of polymer solar cells by developing high efficiency organic solar cells of 10% or more, and is expected to play a big role in the development of organic solar cells that can be bent and worn on the body.
  • FIG. 1 is a schematic diagram of an inverse structure organic solar cell according to the present invention.
  • FIG. 2 is a schematic diagram of an energy structure of an inverse organic solar cell according to the present invention.
  • Figure 3 shows the results of the UPS measurement on each surface according to the PEOz concentration control on the ZnO surface.
  • Figure 4 shows the results of the EFM measurement on each surface according to the PEOz concentration control on the ZnO surface.
  • FIG. 5 is a schematic diagram illustrating a lower work function of ZnO based on the results of UPS and EFM measurements.
  • FIG. 6 is a schematic diagram showing a laminated structure of an inverse structure organic solar cell according to an embodiment of the present invention.
  • FIG. 7 is a schematic diagram showing the energy structure of an inverse structure organic solar cell according to an embodiment of the present invention.
  • FIG. 8 is a current density-voltage graph of the device according to the concentration of PEOz for the organic solar cell of the inverse structure type fabricated in Example 2.
  • FIG. 8 is a current density-voltage graph of the device according to the concentration of PEOz for the organic solar cell of the inverse structure type fabricated in Example 2.
  • FIG. 11 is an AES imaging result of a work function reduction layer, that is, a PEOz layer (ZnO / PEOz 4 mg / ml) and an untreated ZnO surface, by adjusting the concentration of PEOz to 4 mg / ml.
  • a work function reduction layer that is, a PEOz layer (ZnO / PEOz 4 mg / ml) and an untreated ZnO surface, by adjusting the concentration of PEOz to 4 mg / ml.
  • FIG. 13 is a schematic view of an inverse structure organic solar cell according to the present invention including a PEOz layer having a nanopoint structure as a work function reduction layer.
  • the UPS was measured using an ultra-high vacuum (UHV) UPS system (ESCALAB 250Xi, Thermo Scientific) at 1 ⁇ 10 ⁇ 9 mbar using a He I (21.2 eV) UV light source. All samples were biased at -5 V and the energy scale of the UPS spectrum was corrected to the Fermi level of the thermally-evaporated-cleaned Ag substrate.
  • the valence band energy of the ZnO layer was obtained at 7.7 eV from the low binding energy portion of the corresponding UPS spectrum after calibration with the cleaned Ag reference electrode, and the conduction band energy of the ZnO layer was from the valence band energy (3.4 eV) Calculated by subtracting
  • the valence band maximum of the PEOz-coated ZnO layer was calculated using the following equation:
  • E VBM P IN - (E CF - E ON)
  • E VBM , P IN , E CF and E ON are valence band maximum, incident photon energy (21.2 eV), binding energy in the cutoff region, and onset binding energy, respectively.
  • ZnO surface was modified through the concentration control (thickness control) (0, 4, 8 mg / ml) of PEOz using methanol as a solvent, and the electrostatic force microscopy (EMF) was measured as follows.
  • the work function was measured with EFM (XE-150, Park Systems) and calibrated with highly ordered pyrolytic graphite (HOPG).
  • An organic solar cell of an inverse structure type having an energy structure as shown in FIG. 7 in a laminated structure as shown in FIG. 6 while using a PEOz-containing work function reduction coating solution was manufactured as follows.
  • PC71BM purity> 99%
  • DIO 1,8-dioodooctane
  • CB chlorobenzene
  • ZnO precursor solution was dissolved zinc acetate dihydrate (Sigma-Al
  • ITO Indium-tin oxide
  • sheet resistance 10 ⁇ / cm 2
  • ZnO precursor solution was spin coated onto the cleaned ITO-glass substrate and the resulting ITO / ZnO sample was annealed at 200 ° C. for 1 hour in air.
  • the PEOz solution was spin coated onto the surface of the ZnO layer and annealed at 120 ° C. for 15 minutes.
  • PEOz-coated samples were placed in a nitrogen filled glove box for photoactive layer coating.
  • the PTB7-Th: PC 71 BM BHJ layer was spin coated on top of the PEOz-coated ZnO layer and dried for 20 minutes inside the glove box.
  • These samples were then placed in a vacuum chamber in an argon filled glove box. In the vacuum chamber, MoO 3 (10 nm) and Ag (80 nm) were sequentially deposited on top of the BHJ layer through a shadow mask at a vacuum of 2 ⁇ 10 ⁇ 6 Torr.
  • the active area of the device was 0.05 cm 2 or 0.09 cm 2 .
  • the current density-voltage graph of the device according to the concentration of PEOz was calculated using a solar simulator (92250A-1000, Newport-Oriel) and an electrometer (Model 2400, Keithley's solar cell measurement system was used.
  • the external quantum efficiency (EQE) according to the concentration of PEOz for the inverse structure type organic solar cell manufactured in Example 2 is a light source (Tungsten-Halogen lamp, 150 W, ASBN-W, Spectral Products) And a special EQE measurement system equipped with a monochromatic spectrometer (CM110, Spectral Products).
  • the concentration of PEOz was adjusted to 4 mg / ml, thereby modifying the ZnO surface on the glass substrate / ITO, that is, a PEOz layer (ZnO / PEOz 4 mg / ml) and untreated ZnO.
  • Surfaces were measured by Auger Electron Spectroscopy (AES) imaging.
  • a glass substrate / ITO / ZnO layer was laminated under the same conditions as in Example 2, and the surface of the ZnO was modified at a concentration of 4 mg / ml of PEOz. Then, AES imaging was measured.
  • the PEOz layer is formed in a nano-dot structure.
  • the PEOz layer is formed with a nano-dot structure.
  • FIG. 13 A schematic diagram of the inverse structure organic solar cell according to the present invention including the PEOz layer having the nanopoint structure as the work function reduction layer is illustrated in FIG. 13.

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Abstract

La présente invention concerne une composition permettant une réduction d'une fonction de travail d'une couche collectrice d'électrons en oxyde métallique, une cellule solaire organique inversée utilisant ladite composition et un procédé de préparation d'une cellule solaire organique inversée. Selon l'invention, la surface d'une couche collectrice d'électrons en oxyde métallique, qui est un élément constituant d'une cellule solaire organique inversée, est modifiée au moyen d'un polymère neutre et ainsi la fonction de travail de l'oxyde métallique est réduite et un potentiel intégré est augmenté. Des charges peuvent être facilement déplacées et collectées au moyen de la formation de nanoplots polymères grâce au polymère neutre. Par conséquent, le rendement d'une cellule solaire organique inversée utilisant un polymère peut être fortement augmenté.
PCT/KR2016/011865 2015-10-21 2016-10-21 Composition permettant une réduction d'une fonction de travail d'une couche collectrice d'électrons en oxyde métallique, cellule solaire organique inversée utilisant ladite composition, et procédé de préparation d'une cellule solaire organique inversée WO2017069546A1 (fr)

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KR102540847B1 (ko) 2018-03-14 2023-06-05 삼성전자주식회사 전계 발광 소자 및 이를 포함하는 표시 장치
KR102011869B1 (ko) * 2018-07-30 2019-08-19 국민대학교산학협력단 광전변환효율 및 장기안정성이 향상된 페로브스카이트 태양전지 및 이의 제조 방법
KR102670528B1 (ko) * 2021-09-30 2024-05-29 한국화학연구원 SnO2 전자수송층 및 이를 이용한 광소자

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