WO2016163624A1 - Polymère conjugué présentant une bande interdite intermédiaire, procédé pour sa préparation et dispositif électronique organique l'appliquant - Google Patents

Polymère conjugué présentant une bande interdite intermédiaire, procédé pour sa préparation et dispositif électronique organique l'appliquant Download PDF

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WO2016163624A1
WO2016163624A1 PCT/KR2015/013329 KR2015013329W WO2016163624A1 WO 2016163624 A1 WO2016163624 A1 WO 2016163624A1 KR 2015013329 W KR2015013329 W KR 2015013329W WO 2016163624 A1 WO2016163624 A1 WO 2016163624A1
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formula
organic
conjugated polymer
solar cell
electronic device
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Korean (ko)
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문상진
신원석
이종철
이상규
송창은
황국비엣
우한영
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한국화학연구원
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • 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 conjugated polymer having a novel band-gap for a high efficiency organic electronic device, a method for preparing the conjugated polymer, and a high efficiency organic electronic device using the same.
  • Solar cells are devices that can directly convert solar energy into electrical energy by applying the photovoltaic effect.
  • Typical solar cells are made of p-n junctions by doping crystalline silicon (Si), an inorganic semiconductor. Electrons and holes generated by absorbing light diffuse to the p-n junction and are accelerated by the electric field to move to the electrode.
  • the power conversion efficiency of this process is defined as the ratio of the power given to external circuits and the solar power entered into the solar cell, and has been achieved by up to 24% when measured under current virtualized solar irradiation conditions.
  • the conventional inorganic solar cell has shown its limitations in terms of high production cost and supply and demand on materials, and thus, the development of technology for increasing the processing convenience of the solar cell and lowering the production cost has progressed. As a result, the use of low cost-rich organic materials Organic solar cell technology has attracted attention as a new alternative.
  • an organic solar cell generally has a stacked structure divided into a bottom cell and a top cell.
  • electron donor and electron acceptor materials exhibiting absorption of 300 to 600 nm are used, and in the upper layer, electron donor and electron acceptor materials ranging from 600 to 1000 nm are used.
  • P3HT Poly (3-hexylthiophene-2,5-diyl)
  • ICBA Indene-C60 bisadduct
  • Korean Unexamined Patent Publication No. 2010-0088050 discloses an organic semiconductor material of a compound in which an aromatic ring compound or a hetero aromatic ring compound is fused to a structure in which cyclohexane is introduced into fullerene and an organic solar cell device including the same.
  • Korean Patent Publication No. 2014-0099424 discloses high hole mobility and photoelectric conversion efficiency by synthesizing an ICT (Intramolecular Charge Transfer) type polymer polymer composed of an electron-rich monomer and an electron-deficient monomer.
  • ICT Intramolecular Charge Transfer
  • the compounds and polymers disclosed in the prior art have a fill factor (FF) of 41 to 60% and an open circuit voltage (V oc ) of 550 to 800mV, but the degree of improvement effect is insignificant, and thus the photoelectricity. There is a problem that the conversion efficiency (PCE) is not significantly improved.
  • the present invention is to solve the problems of the prior art as described above, has an intermediate band gap (gap) can efficiently absorb a wide range of sunlight and improve the integrity factor (FF) and open circuit voltage
  • the present invention has been made in an effort to provide a novel conjugated polymer having high photoelectric conversion efficiency and that can be used in place of P3HT, a method for preparing the conjugated polymer, and an organic electronic device using the same.
  • the present invention relates to a conjugated polymer represented by the following Equation 1.
  • n is an integer from 2 to 2000; R 1 and R 2 are each independently a linear or branched alkyl group; X 1 , X 2 , X 3 and X 4 are independently of each other H, F, Cl or CN) to be.
  • X 1 , X 2 , X 3 and X 4 of Formula 1 may be independently of each other H or F, R 1 and R 2 of Formula 1 may be independently a branched alkyl group of C8 to C30 Can be.
  • any one or two selected from X 1 , X 2 , X 3 and X 4 of Formula 1 may be F, and the rest may be H.
  • the present invention relates to a method for producing a conjugated polymer for preparing a conjugated polymer represented by the formula (1) by polymerizing the compound of formula (2) and (3).
  • R 'of the formula (2) is a trialkyl tin substituent and Y of the formula (3) may be a halogen substituent.
  • R 'of Formula 2 is trimethyltin and Y of Formula 3 may be any one selected from Br or I.
  • the polymerization may be characterized by polymerization under a palladium-based catalyst.
  • the present invention may include an organic electronic device including the conjugated polymer.
  • the organic electronic device may be any one selected from the group consisting of an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.
  • the present invention provides an organic solar cell including a substrate, a first electrode layer, a buffer layer, a photoelectric conversion layer, an organic thin film layer, and a second electrode layer, wherein at least one of the organic thin film layers includes an organic solar cell including the conjugated polymer.
  • a substrate a first electrode layer, a buffer layer, a photoelectric conversion layer, an organic thin film layer, and a second electrode layer, wherein at least one of the organic thin film layers includes an organic solar cell including the conjugated polymer.
  • the organic thin film layer may be included in the photoelectric conversion layer.
  • the conjugated polymer of the present invention has a condition of an organic semiconductor that can be used as a photoelectric conversion layer (photoactive layer) in an organic solar cell by exhibiting a high open voltage and a high integrity coefficient (FF) by having an intermediate band gap. It has high solubility, which simplifies the manufacturing process of organic electronic devices, and can achieve higher performance than P3HT.
  • FIG. 3 is a graph showing current density-voltage (J-V) characteristic values of organic solar cells manufactured according to Examples 12 to 15 and Comparative Example 1 of the present invention.
  • the present invention relates to a conjugated polymer having an intermediate band gap (gap) for an organic electronic device of high efficiency exhibiting high photoelectric conversion efficiency, and relates to a conjugated polymer represented by the following Chemical Formula 1.
  • n is an integer from 2 to 2000;
  • R 1 and R 2 are each independently a linear or branched alkyl group;
  • X 1 , X 2 , X 3 and X 4 may be each independently H, F, Cl or CN, but is not limited thereto.
  • X 1 , X 2 , X 3 and X 4 of Formula 1 may be independently of each other H or F, R 1 and R 2 of Formula 1 may be independently a branched alkyl group of C8 to C30 And, more preferably, any one or two selected from X 1 , X 2 , X 3 and X 4 of the formula 1 in the present invention may be F, the rest may be H, but is not limited thereto.
  • the present invention includes a method for preparing a conjugated polymer to prepare a conjugated polymer represented by the formula (1) by polymerizing the compound of formula (2) and (3).
  • the conjugated polymer corresponding to Formula 1 of the present invention may be prepared by polymerizing the following Formulas 2 and 3, but is not limited thereto.
  • the R 'and Y may be a substituent that reacts with each other to form a direct bond, but is not limited thereto.
  • the R ' is a trialkyltin substituent
  • the Y may be a halogen substituent, more preferably the R' is trimethyltin, the Y may be any one selected from Br or I, but not limited thereto. It is not.
  • the conjugated polymer of the present invention includes phenylene bisthiophene represented by Formula 2 as an electron donor, and in particular, -F, -Cl, or -CN is 1 to 4 in the phenylene bisthiophene of Formula 2 above.
  • the electron affinity can be increased to reduce the torsion angle due to the interaction between electrons, thereby maintaining the flatness of the polymer, and improving the intermolecular packing property to facilitate hole transfer between the polymer main chains.
  • the conjugated polymer of the present invention can broaden the wavelength range of the absorbable solar spectrum due to the intermolecular interactions strengthened by introducing -F, -Cl or -CN into the formula (2), and through smooth hole transfer
  • the charge mobility can be improved and thus the photoelectric conversion efficiency can be improved.
  • the benzothiadiazole (Benzothiadiazole) represented by the formula (3) in addition to the formula (2) to lower the HOMO (Highest Occupied Molecular Orbital) energy level, thereby lowering the band-gap (high band charge) It can have a high light stability and a high open circuit voltage (Voc) can be improved photoelectric conversion efficiency.
  • a high molecular weight conjugated polymer is preferably used in order to exhibit excellent photoelectric conversion efficiency through proper physical property implementation, but as the molecular weight of the conjugated polymer increases, solubility of the polymer is inhibited to form a uniform thin film. And manufacturing becomes difficult.
  • an alkoxy group into the benzothiadiazole represented by Formula 3
  • the introduction of topographic alkoxy substituents results in higher solubility and higher open voltage compared to linear alkoxy groups, thereby making it possible to exhibit excellent photoelectric conversion efficiency (PCE).
  • the conjugated polymer of the present invention is a conjugated polymer in which the compound of Formula 2 and the compound of Formula 3 are cross-repeatedly introduced, and the non-covalent interaction of X--S and X--O reduces the torsion angle to reduce the polymer backbone. It is possible to maintain the planarity of, and contribute to the improvement of charge mobility by improving the intermolecular packing characteristics.
  • the polymerization of the present invention may be characterized by polymerization under a palladium-based catalyst in a chlorine-based organic solvent.
  • the chlorine-based organic solvent is chloromethane, methylene chloride, chloroform, carbon tetrachloride, 1,1-dichloroethane, 1,2-dichloroethane, ethyl chloride, trichloroethane, 1-chloropropane, 2-chloropropane
  • Chlorine-based organic solvents may be used, and preferably chlorobenzene is not limited thereto.
  • the palladium-based catalysts are palladium acetate (Pd (II) acetate, Pd (OAc) 2 ), palladium chloride (PdCl 2 ) and tetrakis triphenylphosphinepalladium (Tetrakis (triphenyl phosphine) palladium, Pd (PPh 3 )
  • a palladium-based catalyst such as 4 ) may be used.
  • tridibenzylideneacetone dipalladium (Pd 2 (dba) 3 ) may be used, but is not limited thereto.
  • a phosphine ligand such as tri (o-tolyl) phosphine (P (o-Tol) 3 ), etc. may be used together when the palladium-based catalyst is used.
  • the phosphine ligand may electronically stabilize the palladium to help regenerate the palladium compound having the reactive activity so that the palladium catalysis cycle can be maintained.
  • the conjugated polymer of the present invention may be used as an organic electronic device by forming a film by a solution process that is dissolved in an organic solvent and applied to a substrate, and in detail, spin coating, slot die coating, inkjet printing, screen printing It can be applied and coated by any one method selected from the method and the doctor blade method and the like to form a film, but is not limited thereto.
  • the present invention may include an organic electronic device including the conjugated polymer, and may also include an organic electronic device manufactured from the method for preparing the conjugated polymer.
  • the organic electronic device includes an organic light emitting diode (OLED), an organic solar cell (OSC), an organic transistor (OTFT, organic thin-film transistor), and an organic photosensitive drum (OPD).
  • OLED organic light emitting diode
  • OSC organic solar cell
  • OTD organic transistor
  • OPD organic photosensitive drum
  • Photo Detector and an organic memory device may be any one selected from the group consisting of.
  • the organic electronic device may be any conventional organic electronic device that can be recognized by those skilled in the art, and the conjugated polymer may further improve the performance of the organic electronic device through combination with various other electron donors included in the organic electronic device. Can be.
  • the present invention provides an organic solar cell including a substrate, a first electrode layer, a buffer layer, a photoelectric conversion layer, an organic thin film layer, and a second electrode layer, wherein at least one of the organic thin film layers includes an organic solar cell including the conjugated polymer.
  • a substrate a first electrode layer, a buffer layer, a photoelectric conversion layer, an organic thin film layer, and a second electrode layer, wherein at least one of the organic thin film layers includes an organic solar cell including the conjugated polymer.
  • the organic thin film layer may be included in the photoelectric conversion layer of the organic solar cell.
  • a transparent material is preferable, and examples thereof include polyethylene terephthalate (PET), polypropylene (PP), polyimide (PI), polyethylene naphthalate (PEN), and triacetyl cellulose (TAC).
  • the first electrode layer may be formed by applying a transparent material or coating in the form of a film using a method such as spin coating or sputtering on one surface of the substrate.
  • the first electrode layer may be used without particular limitation as long as it has a high work function and has transparency and conductivity, and preferred examples thereof include indium-tin oxide (ITO), ZnO / Ga 2 O 3 , ZnO / Al 2 O 3 , and SnO 2.
  • FTO Fluorine-doped tin oxide
  • a transparent conductive substrate on which a metal such as Ag nanowire or Ag mesh is introduced may be used as the transparent substrate, and more preferably, ITO may be used.
  • the buffer layer formed on top of the first electrode layer is formed of a poly (3,4-ethylenedioxythiophene) [PEDOT / PSS] doped with polystyrene sulfonate (PSS) and a charge life between the electrode and the photoelectric conversion layer.
  • the hole mobility may be improved, and at this time, a solar cell having a positive structure in which electrons fall into the second electrode layer may be formed by using a second electrode layer having a low work function.
  • the manufacturing method of the buffer layer may be introduced through a method such as spin coating.
  • a buffer layer having a low work function such as zinc oxide (ZnO) is used on the first electrode layer and a second electrode layer having a high work function is used, a solar cell having an inverse structure in which electrons fall into the first electrode can be formed.
  • a photoelectric conversion layer may be stacked on the buffer layer.
  • the photoelectric conversion layer is composed of a junction structure of an electron donor and an electron acceptor, and provides a photovoltaic effect (photoelectric conversion effect) through a fast charge transfer phenomenon between the electron donor and the electron acceptor.
  • the photoelectric conversion layer may use the conjugated polymer of the present invention as an electron donor, and PC 71 BM may be used as an electron acceptor.
  • the photoelectric conversion material of the photoelectric conversion layer is preferably blended with 50 to 600 parts by weight of PC 71 BM based on 100 parts by weight of the conjugated polymer.
  • the present invention is not particularly limited as long as the object of the present invention is achieved.
  • the electron accepting action of the PC 71 BM is actively generated, resulting in mobility of the generated electrons. Very good and the light absorption of the conjugated polymer can be made efficiently.
  • the electron acceptor may be a fullerene-based acceptor material such as PC 61 BM and other non-fullerene-based monomolecules or polymers having deeper LUMO levels than donor polymer materials.
  • the photoelectric conversion material prepared by combining the conjugated polymer and PC 71 BM of the present invention may be prepared by dissolving a single organic solvent or two or more organic solvents having different boiling points.
  • the organic solvent used may be any one solvent selected from the group consisting of chloroform, chlorobenzene, 1,2-dichlorobenzene, toluene, xylene, trimethylbenzene, 1,8-diiooctane, 1-chlorobenzene,
  • the solvent selected from the group consisting of diphenyl ether may be used in combination, but is not limited thereto.
  • the solid content of the photoelectric conversion material in the solvent is preferably prepared to contain 1.0 to 3.0 wt%.
  • the present invention is not particularly limited as long as the object of the present invention is achieved, but when the above range is satisfied, the conjugated polymer and PC 71 BM are effectively dissolved to effectively prepare a photoelectric conversion material in a dissolved form in a solvent.
  • the photoelectric conversion material is coated to form a film, a thin film having an appropriate thickness may be formed.
  • the solution in which the photoelectric conversion material is dissolved is applied or coated by any one method selected from spin coating method, slot die coating method, screen printing method, ink jet printing method, and doctor blade method, and is preferably 30 to 800 nm.
  • the photoelectric conversion layer having a thickness of 80 to 400 nm can be prepared.
  • the second electrode layer may be stacked on top of the photoelectric conversion layer by vacuum thermal deposition of a metal material having a low work function such as aluminum at 80 to 200 nm at a vacuum degree of about 10 ⁇ 7 torr or less while the photoelectric conversion layer is introduced.
  • a metal material having a low work function such as aluminum at 80 to 200 nm at a vacuum degree of about 10 ⁇ 7 torr or less while the photoelectric conversion layer is introduced.
  • a metal material having a low work function such as aluminum at 80 to 200 nm at a vacuum degree of about 10 ⁇ 7 torr or less while the photoelectric conversion layer is introduced.
  • the material that can be used as the second electrode include gold, aluminum, copper, silver or alloys thereof, calcium / aluminum alloys, magnesium / silver alloys, aluminum / lithium alloys, and the like, and preferably aluminum or aluminum / Calcium alloys may be used, but are not limited thereto.
  • the molecular weight of the polymer was measured using gel permeation chromatography (GPC) used as polystyrene standard.
  • UV-vis absorption spectra were measured using a Shimadzu UV-2550 model.
  • the solution state of the UV-vis absorption spectrum was measured a solution in which the polymer was dissolved in chloroform, and the film state was measured in a film spin-coated on quartz by dissolving the polymer in the chloroform solution.
  • the optoelectronic device was fabricated using a polymer obtained from the above Examples and Comparative Examples as a p-type electron donor and PC 71 BM (EM index) as an n-type electron acceptor.
  • the polymer and PC 71 BM were dissolved in a mixed solvent of chlorobenzene and 1,8-diiooctane in a weight ratio of 1: 1.5.
  • Optoelectronic devices were fabricated and characterized with ITO / PEDOT: PSS / Polymer + PC 71 BM (1: 1.5 weight ratio) / Ca / Al device structure.
  • Example 8 1,4-Dibromo-2-fluorobenzene was used instead of 1,4-Dibromobenzene, and 1,4-bis (thiophen-2-yl) -2-fluorobenzene was recrystallized using a methanol solvent. , 4-bis (5- (trimethylstannyl) thiophen-2-yl) -2-fluorobenzene was prepared in the same manner except for the recrystallization using ethanol solvent. -yl) -2-fluorobenzene (hereinafter 1F) was obtained in a two-step yield of 45%.
  • 1,4-dibromo-2,5-difluorobenzene was used instead of 1,4-Dibromobenzene, 1,4-bis (thiophen-2-yl) -2,5-difluorobenzene and 1,4-bis Except for recrystallization of (5- (trimethylstannyl) thiophen-2-yl) -2,5-difluorobenzene using a hexane solvent, the remainder is the same process as 1,4-bis (5- (trimethylstannyl) thiophen-2-yl ) -2,5-difluorobenzene (hereinafter 2F) was obtained in a two-step yield of 45%.
  • 1,4-dibromo-2,5-difluorobenzene was used instead of 1,4-Dibromobenzene, 1,4-bis (thiophen-2-yl) -2,3,5,6-tetrafluorobenzene and 1 Except for recrystallization of, 4-bis (5- (trimethylstannyl) thiophen-2-yl) -2,3,5,6-tetrafluorobenzene using an ethanol solvent, the remainder is the same procedure as 1,4-bis (5- (trimethylstannyl) thiophen-2-yl) -2,3,5,6-tetrafluorobenzene (hereinafter 4F) was obtained in a two-step yield of 43%.
  • ITO (Indium tin oxide) glass was washed clean. 1 wt% of a photoactive layer material containing P2-0F: PC 71 BM in a 1: 1.5 weight ratio was dissolved in a chloroform solvent containing 3% by volume of dioodooctane, and then stirred at 50 ° C. for 24 hours to form a photoelectric conversion material. A mixed solution was prepared. Spin coating the photoelectric conversion material mixture on the PEDOT: PSS layer as a coating layer under nitrogen to form a photovoltaic conversion layer of 100 nm, and then transferring Ca to a vacuum evaporator, followed by Ca at a rate of 0.1 nm / s at 2 ⁇ 10 ⁇ 6 torr.
  • Example 12 (2) except for using P2-1F as a new electron donor in Example 12 (2), the rest of the organic solar cell device was manufactured by the same process, and the physical properties of the organic solar cell device through the method of Experiment 4). was measured.
  • Example 12 (2) except for using P2-1F as a new electron donor in Example 12 (2), the rest of the organic solar cell device was manufactured by the same process, and the physical properties of the organic solar cell device through the method of Experiment 4). was measured.
  • Example 12 (2) except for using P2-1F as a new electron donor in Example 12 (2), the rest of the organic solar cell device was manufactured by the same process, and the physical properties of the organic solar cell device through the method of Experiment 4). was measured.
  • P3HT polymer is Rieke Metals. Ins. # 4002-EE grade of was used, the weight average molecular weight of 50,000 ⁇ 70,000 was used.
  • Example 12 (2) except for using P3HT as an electron donor in Example 12 (2), the rest of the organic solar cell device was manufactured by the same procedure, and the physical properties of the organic solar cell device were measured by the method of Experiment 4). .
  • V oc Open circuit voltage [V]
  • the results of Examples 12 to 15 and Comparative Example 1 in FIGS. 3 to 4 the physical properties and photoelectric properties effect of the polymer was changed according to the number of fluorine substituents of the conjugated polymer of the present invention.
  • the conjugated polymer of the present invention has an absorption band at 600 to 700 nm, similar to P3HT, and has an intermediate band gap.
  • the number of fluorine substituents increases, it was confirmed that the light absorption region is finely controlled, and through this, it was confirmed that an organic solar cell device capable of selecting a wavelength to be absorbed through a change in the content of the fluorine substituents.
  • the conjugated polymer of the present invention according to Examples 12 to 15 having a fluorine substituent in comparison with P3HT used as an electron donor as a photoelectric conversion layer When fabricating with a battery device, it was confirmed that the photoelectric efficiency (PCE) of the organic solar cell device was remarkably improved.
  • the organic solar cell device including the conjugated polymer of Example 14 having two fluorine substituents as a photoelectric conversion layer exhibits a remarkable photoelectric efficiency improvement effect, which is about about the organic solar cell device containing P3HT of Comparative Example 1.
  • the conjugated polymer of the present invention exhibits an improved open circuit voltage (V oc ) and a closeness coefficient (FF) than the photoelectric properties of P3HT, which is used as an electron donor in the same region, to absorb light.
  • V oc open circuit voltage
  • FF closeness coefficient
  • PCE photoelectric conversion efficiency
  • the conjugated polymer according to Examples 12 to 15 of the present invention can be used as a material for a high performance organic solar cell device in place of P3HT, and all organic electronic device fields in which P3HT is used as well as organic solar cell devices. It was confirmed that it is suitable as a material of.

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Abstract

La présente invention concerne un nouveau polymère conjugué présentant une bande interdite intermédiaire, pour un dispositif électronique organique hautement efficace, un procédé pour sa préparation et un dispositif électronique organique hautement efficace l'appliquant et, plus particulièrement, un polymère conjugué et un dispositif électronique organique l'appliquant, le polymère conjugué présentant une bande interdite intermédiaire, au moyen d'une polymérisation de benzothiadiazole, qui présente un substituant alcoxy, et de phénylène-bisthiophène, qui présente un substituant présentant une forte affinité pour les électrons. Un dispositif électronique organique, qui présente une efficacité élevée de conversion photoélectrique et peut être utilisé à la place de P3HT, peut être obtenu par absorption sélective et efficace de la lumière du soleil d'une plage de 650 à 700 nm, au moyen du polymère conjugué de la présente invention, et l'amélioration du facteur de remplissage (FF) et une tension de circuit ouvert.
PCT/KR2015/013329 2015-04-07 2015-12-07 Polymère conjugué présentant une bande interdite intermédiaire, procédé pour sa préparation et dispositif électronique organique l'appliquant WO2016163624A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110168762A (zh) * 2017-06-23 2019-08-23 株式会社Lg化学 有机太阳能电池
CN110199401A (zh) * 2017-06-27 2019-09-03 株式会社Lg化学 有机太阳能电池

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120121358A (ko) * 2011-04-26 2012-11-05 국립대학법인 울산과학기술대학교 산학협력단 좁은 밴드갭을 갖는 평면성 공중합물 및 이를 이용한 유기 고분자 박막 태양 전지 소자
KR20140058653A (ko) * 2011-08-26 2014-05-14 메르크 파텐트 게엠베하 유기 반도체 배합물
KR20140099424A (ko) * 2013-02-01 2014-08-12 부산대학교 산학협력단 고효율 유기 박막 태양전지를 위한 신규의 고분자 재료 및 이를 이용한 유기 박막 태양전지

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101043627B1 (ko) 2009-01-29 2011-06-24 한국화학연구원 플러렌 유도체를 함유한 유기태양전지 소자
KR20150130192A (ko) * 2014-05-13 2015-11-23 주식회사 엘지화학 공중합체 및 이를 포함하는 유기 태양 전지

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120121358A (ko) * 2011-04-26 2012-11-05 국립대학법인 울산과학기술대학교 산학협력단 좁은 밴드갭을 갖는 평면성 공중합물 및 이를 이용한 유기 고분자 박막 태양 전지 소자
KR20140058653A (ko) * 2011-08-26 2014-05-14 메르크 파텐트 게엠베하 유기 반도체 배합물
KR20140099424A (ko) * 2013-02-01 2014-08-12 부산대학교 산학협력단 고효율 유기 박막 태양전지를 위한 신규의 고분자 재료 및 이를 이용한 유기 박막 태양전지

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BUNDGAARD, EVA ET AL.: "Low-Band-Gap Conjugated Polymers based on Thiophene, Benzothiadiaxole, and Benzobis (thiadiaxole", MACROMOLECULES, vol. 39, no. Iss. 8, 2006, pages 2823 - 2831, XP055308116 *
JIN, ENQUAN ET AL.: "Dibenzothiophene-based Planar Conjugated Polymers for High Efficiency Polymer Solar Cells", MACROMOLECULES, vol. 45, no. Iss. 19, 2012, pages 7843 - 7854, XP055308116 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110168762A (zh) * 2017-06-23 2019-08-23 株式会社Lg化学 有机太阳能电池
EP3557640A4 (fr) * 2017-06-23 2020-01-15 LG Chem, Ltd. Cellule solaire organique
CN110199401A (zh) * 2017-06-27 2019-09-03 株式会社Lg化学 有机太阳能电池
CN110199401B (zh) * 2017-06-27 2023-05-12 株式会社Lg化学 有机太阳能电池

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