WO2017081623A1 - Copolymère conjugué fluoré photoactif - Google Patents

Copolymère conjugué fluoré photoactif Download PDF

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Publication number
WO2017081623A1
WO2017081623A1 PCT/IB2016/056743 IB2016056743W WO2017081623A1 WO 2017081623 A1 WO2017081623 A1 WO 2017081623A1 IB 2016056743 W IB2016056743 W IB 2016056743W WO 2017081623 A1 WO2017081623 A1 WO 2017081623A1
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Prior art keywords
branched
unsaturated
saturated
linear
general formula
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PCT/IB2016/056743
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English (en)
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Andrea Pellegrino
Fiorenza SIMONE
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Eni S.P.A.
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Publication of WO2017081623A1 publication Critical patent/WO2017081623A1/fr

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    • 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
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • 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
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50—Photovoltaic [PV] devices
    • 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 photoactive fluorinated conjugated copolymer.
  • the present invention relates to a photoactive fluorinated conjugated copolymer comprising units in which there is a donor group and a benzothiadiazole group, and units in which there is a donor group and a benzotriazole group, at least one of said benzothiadiazole group and said benzotriazole group being fluorinated.
  • the present invention also relates to the use of said photoactive fluorinated conjugated copolymer in the manufacture of photovoltaic devices (or solar devices) such as, for example, photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), either on rigid support, or on flexible support.
  • Photovoltaic devices are devices able to convert the energy of light radiation into electrical energy.
  • photovoltaic devices or solar devices
  • the chemical/physical properties of inorganic photoactive materials in particular highly pure crystalline silicon.
  • organic photovoltaic devices or solar devices
  • organic photovoltaic cells or solar cells.
  • said organic materials are characterized by their relative ease of synthesis, a low production cost, a reduced weight of the relative photovoltaic devices (or solar devices), as well as allowing said organic materials to be
  • organic photovoltaic devices such as, for example, organic photovoltaic cells (or solar cells)
  • organic photovoltaic cells or solar cells
  • the electron acceptor compounds most frequently used in organic photovoltaic devices are fulierene derivatives, in particular PC61BM (6, 6-phenyf-C61 -butyric acid methyl ester) or PC71 BM (6, 6-phenyl-C71 -butyric acid methyl ester), which have led to the highest efficiencies when mixed with electron donor compounds selected from ⁇ -conjugated polymers such as, for example, polythiophenes ( ⁇ > 5%), polycarbazoles ( > 6%), derivatives of poly(thienothiophene)-benzodithiophene (PTB) ( ⁇ > 8%).
  • ⁇ -conjugated polymers such as, for example, polythiophenes ( ⁇ > 5%), polycarbazoles ( > 6%), derivatives of poly(thienothiophene)-benzodithiophen
  • the photoabsorption process with the formation of the exciton and subsequent loss of an electron to the electron acceptor compound implies the excitation of an electron from the HOMO ("Highest Occupied Molecular Orbital") to the LUMO ("Lowest Unoccupied Molecular Orbital") of the electron donor compound and, subsequently, the passage from this to the LUMO of the electron acceptor compound.
  • the amount of light that photovoltaic materials can absorb the higher said quantity, the higher the currents that could potentially be produced; said property is in turn attributable to the size of the absorption spectrum of the photovoltaic materials used and how intense said absorption is (i.e. how high their molar extinction coefficient is ( ⁇ );
  • the efficiency with which the charges can percolate to the electrodes attributable to the mobility of the electron holes towards the anode through the donor compound and of the electrons towards the cathode through the electron acceptor compound.
  • the organic photovoltaic ceils are made by introducing between two electrodes, usually made of indium tin oxide (ITO)
  • a film is deposited, based on an aqueous suspension of PEDOT:PSS [poly(3,4-ethylenedioxythiophene)polystyrene sulfonate], making use of appropriate application techniques, such as "spin-coating”, “spray- coating”, “ink-jet printing”, and the like.
  • the counter electrode is deposited [(Al) cathode] on the dried film.
  • electron-rich groups and acceptor groups (i.e. electron-poor groups) are known in the state of the art.
  • Fluorinated conjugated polymers are also known that may be used in photovoltaic applications as reported, for example, by: Price S. C. et al., in “Journal of the American Chemical Society' (201 1 ), Vol. 133, pag. 4625-4631 ; Liu Y. et al., in "Nature
  • conjugated polymers in particular fluorinated conjugated polymers
  • said conjugated polymers can have some drawbacks such as, for example, low processabi!ily as they are not very soluble, and poor interest for industry because of poor scalability due to their high synthetic complexity.
  • the Applicant has now found photoactive fluorinated conjugated copolymers comprising units in which there is a donor group and a benzothiadiazole group, and units in which there is a donor group and a benzotriazoie group, at least one of said benzothiadiazole group and said benzotriazoie group being fluorinated, which have low synthetic complexity, high solubility and high power conversion efficiency (PCE), said power conversion efficiency (PCE) being defined as the ratio between the number of electrons produced and the number of photons with which the surface unit is irradiated.
  • PCE power conversion efficiency
  • Said photoactive fluorinated copolymers may be advantageously used in the manufacture of photovoltaic devices (or solar devices) such as, for example, photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), either on rigid support, or on flexible support.
  • photovoltaic devices or solar devices
  • photovoltaic cells or solar cells
  • photovoltaic modules or solar modules
  • the subject matter of the present invention is a photoactive fluorinated
  • D represents a d rmulae (II), (III), (IV):
  • Ri, R 2 , R 3 and R 4 represent a hydrogen atom; or they are selected from linear or branched, saturated or unsaturated C C 2 0 alkyl groups, preferably C 2 -C 0 , optionally containing heteroatoms;
  • n 1 or 2;
  • BTD represents a benzothiadiazole group having general formula (V):
  • X, and X 2> mutually identical represent a hydrogen atom; or a fluorine atom; or they are selected from linear or branched, saturated or unsaturated Ci C 20 alkyl groups, preferably C 2 -C C , optionally containing heteroatoms, linear or branched, saturated or unsaturated C C 20 alkoxy groups, preferably C 2 -C 0 ;
  • BTZ represents a benzotriazole group having general formula (VI):
  • R 5 is selected from linear or branched, saturated or unsaturated C C 2 o alky! groups, preferably C 8 -C 18 , optionally containing heteroatoms;
  • X 2 mutually identical, represent a hydrogen atom; or a fluorine atom; or they are selected from linear or branched, saturated or unsaturated d-C 20 alkyl groups, preferably C 2 -C 0 , optionally containing heteroatoms, linear or branched, saturated or unsaturated C C 20 alkoxy groups, preferably C 2 -C 10 ;
  • the molar ratio between donor group D, benzothiadiazole group BTD and benzotriazole group BTZ is ranging from 1:0.2:0.8 to 1 :0.8:0.2, preferably it is 1 :0.5:0.5:
  • said photoactive fluorinated conjugated copolymer has the following general formula (lb):
  • D represents a donor group having general formula (III):
  • R 3 and R 4 are selected from linear or branched, saturated or unsaturated Ci-C 2 o alky! groups, preferably C 2 -C 10 , optionally containing heteroatoms;
  • BTD represents a benzothiadiazole group having general formula (V):
  • X 2 mutually identical, represent a hydrogen atom; or a fluorine atom; or they are selected from linear or branched, saturated or unsaturated C r C 2 o alkyl groups, preferably C 2 -Ci 0 , optionally containing heteroatoms, linear or branched, saturated or unsaturated d-C 2 o alkoxy groups, preferably C 2 -Ci 0 ;
  • R 5 is selected from linear or branched, saturated or unsaturated C 1 -C 20 aikyi groups, preferably C 8 C ia> optionally containing heteroatoms;
  • X-i and X 2 mutually identical, represent a hydrogen atom; or a fluorine atom; or they are selected from linear or branched, saturated or unsaturated Ci-C 2Q alkyi groups, preferably C 2 -C 10 , optionally containing heteroatoms, linear or branched, saturated or unsaturated CrC 20 alkoxy groups, preferably C 2 -C 10 ;
  • x is a number ranging from 0.2 to 100, preferably ranging from 0.4 to 20;
  • y is a number ranging from 0.2 to 100, preferably ranging from 0.4 to 20.
  • Iky I group means an alkyl group having from 1 to 20 carbon atoms, linear or branched.
  • C C 32 alkyl groups are: methyl, ethyl, propyl, iso- propyl, butyl, f-butyl, hexyl, heptyl, octyl, decyl, tetradecyl, dodecyl, hexadecyl, octadecyl, eicosyl, 1 -ethyl propyl, 1-butylpentyl, 1-hexylheptyl, 1-octylnonyl, 1- dodecyltridecyl, 1 -hexadecylheptadecyl, 1 -octadecylnonadecyl, 2-ethylhexyl, 2- ethyloctyl, 2-ethyldecyl
  • alkyl groups C 1 -C 20 optionally containing heteroatoms means alkyl groups having from 1 to 20 carbon atoms, linear or branched, saturated or unsaturated, wherein at least one of the hydrogen atoms is substituted with a heteroatom selected from halogens, for example, fluorine, chlorine, bromine, preferably fluorine; nitrogen; sulfur; oxygen.
  • C C 20 alkyl groups optionally containing heteroatoms are: fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, 2,2,2- trifluoroethyl, 2,2,2-trichloroethyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, perfluoropentyl, perfluoroctyl, perfluorodecyl, oxymethyl, thiomethyl, thioethyl, thiohexanoyl, thiooctanoyl, thiodecanyl, dimethylamine, propylamine, dioctylamine.
  • Ci-C 20 alkoxy groups means groups comprising an oxygen atom to which a linear or branched, saturated or unsaturated C-C 20 alkyl group is bonded.
  • Specific examples of Ci-C 20 alkoxy groups are: methoxyl, ethoxyl, n-propoxyl, so-propoxyl, n- butoxyl, /so-butoxyl, f-butoxyl, pentoxyl, hexyloxyl, 2-ethylhexyloxyl, 3-ethyl hexyloxyl, heptyloxyl, octyloxyl, nonyloxyl, decyloxyl, dodecyloxyl.
  • said photoactive fiuorinated conjugated copolymer may have an average molecular weight (Mw) ranging from 20 kDa to 200 kDa, preferably ranging from 30 kDa to 180 kDa. Said average
  • molecular weight ( w) may be calculated as specified below.
  • said photoactive fluorinated conjugated copolymer may have a number average molecular weight (Mn) ranging from 10 kDa to 100 kDa, preferably ranging from 12 kDa to 80 kDa. Said number average molecular weight (Mn) may be calculated as specified below.
  • the photoactive fluorinated conjugated copolymer according to the present invention may be synthesized through processes known in the state of the art such as, for example, the Stumble reaction, the Suzuki reaction, as described, for example, in patent application US 2012/0157357; or by Kotowski D. et al., in "Journal uf Materials
  • Said photoactive fluorinated conjugated copolymer may be used in the manufacture of photovoltaic devices (or solar devices) such as, for example, photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), either on rigid support, or on flexible support.
  • photovoltaic devices or solar devices
  • photovoltaic cells or solar cells
  • photovoltaic modules or solar modules
  • the present invention therefore also relates to the use of said photoactive fluorinated conjugated copolymer in the manufacture of photovoltaic devices (or solar devices) such as, for example, photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), either on rigid support, or on flexible support.
  • photovoltaic devices or solar devices
  • photovoltaic cells or solar cells
  • photovoltaic modules or solar modules
  • a photovoltaic device or solar device
  • thai may be selected, for example, from photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), either on rigid support, or on flexible support, comprising at least one photoactive fluorinated conjugated copolymer described above.
  • the molecular weight of the copolymers obtained operating in accordance with the following examples was calculated through Gel Permeation Chromatography (GPC) on Agilent 220 equipment, using HT5432 columns, with trichlorobenzene eluent, at
  • the average molecular weight (Mw) and the number average molecular weight (Mn) are provided.
  • the reaction mixture obtained was heated to 70°C and subsequently 40 mg (0.032
  • reaction mixture obtained was heated to 70°C and subsequently 40 mg (0.032 mmol) of tetrakis triphenylphosphine palladium [Pd(PPh 3 ) 4 ] (Aldrich) and 2 ml of distilled toluene (Aldrich) were added. Subsequently, the reaction mixture obtained was brought to boiling point and left to react for 40 hours. Subsequently, 1 ml of
  • reaction mixture obtained was heated to 70°C and subsequently 34 mg (0.029 mmol) of tetrakis triphenylphosphine palladium [Pd(PPh 3 ) 4 ] (Aldrich) and 2 ml of distilled toluene (Aldrich) were added. Subsequently, the reaction mixture obtained was brought to boiling point and left to react for 40 hours. Subsequently, 1 ml of
  • reaction mixture obtained was heated to 70°C and subsequently 20 mg (0.017 mmol) of tetrakis triphenylphosphine palladium [Pd(PPh 3 ) ] (Aldrich) and 2 ml of distilled toluene (Aldrich) were added. Subsequently, the reaction mixture obtained was brought to boiling point and left to react for 40 hours. Subsequently, 1 ml of

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Photovoltaic Devices (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention porte sur un copolymère conjugué fluoré photoactif comprenant des unités ayant la formule générale (I) : -(D-BTD)- (I) et des unités ayant la formule générale (Ia) : -(D-BTZ)- (Ia) dans lesquelles : D représente un groupe donneur ayant les formules générales suivantes (II), (III), (IV), dans lesquelles R1, R2, R3 et R4, identiques ou différents, représentent un atome d'hydrogène ou sont choisis parmi les groupes alkyle en C1 à C20 linéaires ou ramifiés, saturés ou insaturés, de préférence en C2 à C10, contenant éventuellement des hétéroatomes ; n vaut 1 ou 2 ; BTD représente un groupe benzothiadiazole ayant la formule générale (V) dans laquelle X1 et X2, identiques l'un à l'autre, représentent un atome d'hydrogène ou un atome de fluor, ou sont choisis parmi les groupes alkyle en C1 à C20 linéaires ou ramifiés, saturés ou insaturés, de préférence en C2 à C10, contenant éventuellement des hétéroatomes, et les groupes alcoxy en C1 à C20 linéaires ou ramifiés, saturés ou insaturés, de préférence en C2 à C10 ; BTZ représente un groupe benzotriazole ayant la formule générale (VI) dans laquelle R5 est choisi parmi les groupes alkyle en 1 à C20 linéaires ou ramifiés, saturés ou insaturés, de préférence en C8 à C18, contenant éventuellement des hétéroatomes ; X1 et X2, identiques l'un à l'autre, représentent un atome d'hydrogène ou un atome de fluor, ou sont choisis parmi les groupes alkyle en C1 à C20 linéaires ou ramifiés, saturés ou insaturés, de préférence en C2 à C10, contenant éventuellement des hétéroatomes, et les groupes alkyle en C1 à C20 linéaires ou ramifiés, saturés ou insaturés, de préférence en C2 à C10 ; à condition que, dans au moins un du groupe benzothiadiazole de formule générale (V) et du groupe benzotriazole de formule générale (VI), X1 et X2, identiques l'un à l'autre, représentent un atome de fluor. Ledit polymère conjugué fluoré photoactif peut être utilisé avantageusement dans la fabrication de dispositifs photovoltaïques (ou dispositifs solaires) tels que, par exemple, des cellules photovoltaïques (ou cellules solaires), des modules photovoltaïques (ou modules solaires), soit sur support rigide soit sur support souple.
PCT/IB2016/056743 2015-11-10 2016-11-09 Copolymère conjugué fluoré photoactif WO2017081623A1 (fr)

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ITUB2015A005427A ITUB20155427A1 (it) 2015-11-10 2015-11-10 Copolimero coniugato fotoattivo fluorurato
IT102015000070788 2015-11-10

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020058860A1 (fr) * 2018-09-19 2020-03-26 Eni S.P.A. Polymères conjugués comprenant un dérivé d'indacén-4-one, procédé pour leur préparation et dispositifs photovoltaïques les comprenant

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011156478A2 (fr) * 2010-06-08 2011-12-15 The University Of North Carolina At Chapel Hill Polymères, dont les largeurs de bande interdite sont accordables, et qui sont destinés à des applications photoniques et électroniques
WO2013120591A2 (fr) * 2012-02-15 2013-08-22 Merck Patent Gmbh Polymères conjugués
JP2014053383A (ja) * 2012-09-05 2014-03-20 Konica Minolta Inc タンデム型の有機光電変換素子およびこれを用いた太陽電池

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011156478A2 (fr) * 2010-06-08 2011-12-15 The University Of North Carolina At Chapel Hill Polymères, dont les largeurs de bande interdite sont accordables, et qui sont destinés à des applications photoniques et électroniques
WO2013120591A2 (fr) * 2012-02-15 2013-08-22 Merck Patent Gmbh Polymères conjugués
JP2014053383A (ja) * 2012-09-05 2014-03-20 Konica Minolta Inc タンデム型の有機光電変換素子およびこれを用いた太陽電池

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020058860A1 (fr) * 2018-09-19 2020-03-26 Eni S.P.A. Polymères conjugués comprenant un dérivé d'indacén-4-one, procédé pour leur préparation et dispositifs photovoltaïques les comprenant
CN112739743A (zh) * 2018-09-19 2021-04-30 艾尼股份公司 包含引达省-4-酮衍生物的共轭聚合物、其制备方法和包括其的光伏装置
US11430957B2 (en) 2018-09-19 2022-08-30 Eni S.P.A. Conjugated polymers including an indacen-4-one derivative, procedure for their preparation and photovoltaic devices comprising the same

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