WO2021167214A1 - Matériau de transport de trous pour cellule solaire, et cellule solaire le comprenant - Google Patents

Matériau de transport de trous pour cellule solaire, et cellule solaire le comprenant Download PDF

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Publication number
WO2021167214A1
WO2021167214A1 PCT/KR2020/017803 KR2020017803W WO2021167214A1 WO 2021167214 A1 WO2021167214 A1 WO 2021167214A1 KR 2020017803 W KR2020017803 W KR 2020017803W WO 2021167214 A1 WO2021167214 A1 WO 2021167214A1
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formula
solar cell
hole transport
independently
transport material
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PCT/KR2020/017803
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English (en)
Korean (ko)
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양창덕
정민규
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울산과학기술원
한국동서발전(주)
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Publication of WO2021167214A1 publication Critical patent/WO2021167214A1/fr

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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
    • 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
    • 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 hole transport material for a solar cell and a solar cell comprising the same.
  • Solar cell technology is a technology that directly converts light into electrical energy, and most of the solar cells being put into practical use are inorganic solar cells using inorganic materials such as silicon.
  • the manufacturing cost of the inorganic solar cell is increased due to the complicated manufacturing process and the material is expensive, the manufacturing cost is low through a relatively simple manufacturing process and research on the organic solar cell having a low material cost is being actively conducted.
  • organic solar cells the structure of BHJ is deteriorated by moisture or oxygen in the air, so that its efficiency is rapidly reduced, that is, there is a big problem in the stability of the solar cell.
  • the price increases.
  • the current perovskite solar cell is the closest to commercialization based on excellent photovoltaic characteristics, cost reduction and easy process among next-generation solar cells including dye-sensitized and organic solar cells, and full-scale research on stability and large area is required. .
  • the perovskite solar cell without the hole transport material showed lower charge extraction and charge recombination at the interface than the perovskite solar cell containing the hole transport material, indicating a decrease in the open circuit voltage and charge rate.
  • HTM plays an important role.
  • perovskite solar cells have been actively studied for several years due to their unique photochemical properties, strong light absorption ability and high efficiency, and have recently achieved efficiencies of 20% or more.
  • the transport capability of the hole transport material is one of the important points, but there is a problem in that the materials used for the hole transport layer of the currently reported high-efficiency perovskite solar cell are limited.
  • One object of the present invention is to provide a hole transport material for a solar cell excellent in performance to be able to replace the conventional hole transport material.
  • Another object of the present invention is to provide a solar cell including the hole transport material for a solar cell in a hole transport layer.
  • a hole transport material for a solar cell represented by the following formula (1):
  • Ar 1 , Ar 2 , Ar 3 , and Ar 4 are each independently a phenyl or naphthyl group substituted with 0 to 4 fluorine (F) atoms,
  • a 1 , A 2 , A 3 , A 4 , A 11 , A 12 , A 13 , and A 14 are each independently a single bond, an oxygen (O) atom, or a sulfur (S) atom,
  • R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 , and R 14 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms;
  • n 11 , n 12 , n 13 , and n 14 are each independently an integer of 0 to 4,
  • Ar 1 , Ar 2 , Ar 3 , and Ar 4 are a phenyl group, and A 1 , A 2 , A 3 , A 4 , A 11 , A 12 , A 13 , and A 14 are an oxygen (O) atom.
  • Ar 1 , Ar 2 , Ar 3 , and Ar 4 is substituted with one or more fluorine atoms.
  • a solar cell comprising the hole transport material in the hole transport layer.
  • the hole transport material according to the present invention not only has excellent properties of the material itself, such as maintaining excellent stability without deterioration even for a long period of time, but also the solar cell including it in the hole transport layer has the same device performance as PCE. It shows an improvement compared to the case where a transport material is used.
  • FIG. 1 is a diagram schematically showing the structure of an n-i-p-perovskite solar cell prepared in Comparative Examples and Preparation Examples of the present invention.
  • FIG. 2A to 2C are graphs showing J-V curves of solar cells manufactured according to Comparative Examples and Preparation Examples
  • FIG. 2D is a graph showing a distribution of PCE values of each solar cell.
  • FIGS. 3B to 3D are graphs showing the change in JV curve with time will be.
  • perovskite solar cell refers to a solar cell including an organic-inorganic halide material having a perovskite crystal structure.
  • a hole transport material for a solar cell represented by the following formula (1), specifically, a hole transport material for a perovskite solar cell:
  • Ar 1 , Ar 2 , Ar 3 , and Ar 4 are each independently a phenyl or naphthyl group substituted with 0 to 4 fluorine (F) atoms; Specifically, each independently may be one substituted with 0 to 2 fluorine atoms; More specifically, each independently may be a phenyl group substituted with 0 to 2 fluorine atoms.
  • the material of Formula 1 may be one in which at least one of Ar 1 , Ar 2 , Ar 3 , and Ar 4 is substituted with one or two fluorine (F) atoms, and in another embodiment Accordingly, at least one of Ar 1 , Ar 2 , Ar 3 , and Ar 4 may be a phenyl group substituted with one or two fluorine (F) atoms.
  • a 1 , A 2 , A 3 , A 4 , A 11 , A 12 , A 13 , and A 14 are each independently a single bond, an oxygen (O) atom, or sulfur (S ) is an atom; Specifically, each independently may be a single bond or an oxygen atom.
  • a 1 , A 2 , A 3 , and A 4 may be identical to each other
  • the material of Formula 1 in the material of Formula 1 , at least one of A 1 , A 2 , A 3 , A 4 , A 11 , A 12 , A 13 , and A 14 is an oxygen (O) atom or a sulfur (S) atom may be According to another embodiment, the material of formula 1 has a set of A 1 , A 2 , A 3 , and A 4 and one of the sets of A 11 , A 12 , A 13 , and A 14 are all oxygen atoms and the other One set may be an oxygen atom or a single bond.
  • R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 , and R 14 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; Specifically, it may be a hydrogen atom or a branched or straight-chain alkyl group having 1 to 4 carbon atoms.
  • R 1 , R 2 , R 3 , and R 4 may be identical to each other
  • R 11 , R 12 , R 13 , and R 14 may be identical to each other, provided that R 1 , R 2 , R
  • the set of 3 , and R 4 and the set of R 11 , R 12 , R 13 , and R 14 may be the same as or different from each other.
  • R 1 , R 2 , R 3 , and R 4 are each independently an alkyl group having 1 to 8 carbon atoms, and R 11 , R 12 , R 13 , and R 14 are each independently , a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; or R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and R 11 , R 12 , R 13 , and R 14 are each independently, each having 1 to 8 carbon atoms It may be an alkyl group.
  • n 11 , n 12 , n 13 , and n 14 are each independently an integer of 0 to 4; Specifically, each independently may be an integer of 0 to 2. According to one embodiment, n 11 , n 12 , n 13 , and n 14 may be 0.
  • the material of Formula 1 may be represented by Formula 2 below:
  • a 1 , A 2 , A 3 , A 4 , A 11 , A 12 , A 13 , A 14 , R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 , R 14 , n 11 , n 12 , n 13 , and n 14 are as defined in Formula 1 above,
  • n 1 , n 2 , n 3 , and n 4 are each independently an integer of 0 to 4,
  • n 1 , n 2 , n 3 , and n 4 are oxygen (O) atoms
  • at least one of n 1 , n 2 , n 3 , and n 4 . is an integer greater than or equal to 1.
  • a 1 , A 2 , A 3 , A 4 , A 11 , A 12 , A 13 , and A 14 are the same as each other, and an oxygen (O) atom or sulfur (S) atom
  • R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 , and R 14 are the same as each other and are an alkyl group having 1 to 8 carbon atoms
  • n 1 , n 2 , n 3 , n 4 , n 11 , n 12 , n 13 , and n 14 are integers from 0 to 2 with the proviso that n 1 , n 2 , n 3 , n 4 , n 11 , n 12 , n 13 , and n
  • At least one of 14 may be an integer of 1 or 2.
  • the material of Formula 1 may be represented by Formula 3 below:
  • a 1 , A 2 , A 3 , A 4 , A 11 , A 12 , A 13 , A 14 , R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 , R 14 , n 11 , n 12 , n 13 , and n 14 are as defined in Formula 1 above,
  • n 1 , n 2 , n 3 , and n 4 are each independently an integer of 0 to 4.
  • the hole transport material of the present invention may be selected from the group consisting of the following Chemical Formulas 4 to 10:
  • the hole transport material according to the present invention can be synthesized through an amination reaction, specifically, a coupling reaction between an aryl halide and an amine under a Pd catalyst, and more specifically, a Buchwald-Hartwig C-N coupling reaction.
  • a method for manufacturing a hole transport material according to an embodiment of the present invention is as follows [Scheme 1]:
  • Examples of the diphenylamine derivative in [Scheme 1] include the following derivatives:
  • a solar cell comprising the hole transport material in the hole transport layer.
  • the solar cell may be a perovskite solar cell.
  • the solar cell may include a first electrode; a photoactive layer disposed on the first electrode and comprising perovskite; and a hole transport layer disposed on the photoactive layer.
  • the solar cell may further include a second electrode on the hole transport layer;
  • An electron transport layer may be further included between the first electrode and the photoactive layer.
  • the photoactive layer further comprises a photoactive material other than the perovskite material, for example a semiconductor material, or the photoactive layer further comprises, in addition to the layer comprising the perovskite, other It may further include another layer comprising a photoactive material, for example a semiconductor layer.
  • the first electrode may be one of an anode and a cathode
  • the second electrode may be the other one of an anode and a cathode.
  • either or both of the first electrode and the second electrode may be coated on the substrate.
  • the hole transport layer after dissolving a hole transport material in a solvent or dispersing it in a dispersion medium, spin coating method, spray coating method, screen printing method, bar coating method, inkjet printing method, slot die coating method and the like, and may be formed by thermal evaporation or sputtering under vacuum.
  • 2,2',7,7'-tetrabromo-9,9'-spirobifluorene 500 mg, 0.79 mmol
  • DPA-mF 840.7 mg, 3.40 mmol
  • tri- tert-Butylphosphonium tetrafluoroborate 13.8 mg, 0.047 mmol
  • sodium tert-butoxide 456.5 mg, 4.75 mmol
  • the crude product is purified by silica gel column chromatography using as a solid to obtain spiro-mF.
  • the resulting solid is dissolved in THF and mixed with hydrazine hydrate.After vigorous stirring, the solution is in methanol (200mL) Precipitation, filtration and washing with methanol Drying in a high vacuum oven afforded the desired product spiro-mF as a pale yellow solid (550 mg, 53.7% yield).
  • DPA-oF was synthesized according to the same procedure as in Synthesis Example 1-(1) of DPA-mF, except that 4-bromo-3-fluoro-1-methoxybenzene was used. A green liquid was obtained (4.9 g, 81.3% yield).
  • Spiro-oF was synthesized according to the same procedure as in Synthesis Example 1-(2) of spiro-mF, except that DPA-oF was used instead of DPA-mF. A pale yellow solid was obtained (513 mg, 50.1% yield).
  • F-methylDPA was synthesized according to the same procedure as in Synthesis Example 1-(1) of DPA-mF, except that p-toluidine and 4-bromo-2-fluorotoluene were used. A white solid was obtained (5.03 g, 84.3% yield).
  • Spiro-TTBF was synthesized according to the same procedure as in Synthesis Example 1-(2) of spiro-mF, except that F-methylDPA was used instead of DPA-mF.
  • the crude product was purified by silica gel column chromatography using hexane/methylene chloride (2:1, v/v) as eluent to give spiro-TTBF as a solid. A pale yellow solid was obtained (468 mg, 50.6% yield).
  • DPA-Naph was synthesized according to the same procedure as in Synthesis Example 1-(1) of DPA-mF. A brown solid was obtained (5.64 g, 83.5% yield).
  • DPA-OP was synthesized according to the same procedure as in Synthesis Example 1-(1) of DPA-mF. A brown solid was obtained (4.85 g, 79.8% yield).
  • DPA-ON was synthesized according to the same procedure as in Synthesis Example 1-(1) of DPA-mF. A brown solid was obtained (6.56 g, 82.6% yield).
  • IPA isopropyl alcohol
  • the paste was diluted with 2-methoxyethanol/terpineol (78:22 w/w) 1:6 (g/g).
  • the prepared substrate was heated once more at 500° C. for 1 hour.
  • a solution of lithium bis(trifluoromethanesulfonyl)imide (Li-TFSI) in 0.1 M acetonitrile was spin-coated at 3000 rpm for 30 seconds. Thereafter, the Li-treated substrate was sintered at 500° C. for 1 hour.
  • 1,550 mg mL -1 FAPbI 3 and 61 mg MACl were dissolved in a mixture of DMF and DMSO (4:1 volume ratio).
  • 70 ⁇ L of the filtered solution was spin coated on the mp-TiO 2 layer at 8000 rpm.
  • 1 mL diethyl ether was added dropwise for 10 seconds after spin.
  • the film was annealed at 150° C. for 10 minutes on a hotplate.
  • 20 mM n-octylammonium iodide was spin coated on the perovskite layer at 3000 rpm and the film was heated at 100° C. for 1 minute.
  • Spiro-oF (Formula 5) (90.9 mg mL ⁇ 1 ), 15-32 ⁇ L of Li-TFSI, 39 ⁇ L of tBP, and 10 ⁇ L of FK209 were used to prepare the hole transport material, spiro-oF For dissolution, the perovskite solar solution was heated in the same manner as in the comparative example above, except that the spiro-oF solution was heated at 70 °C for 30 min after the addition of tBP for dissolution, and Li-TSFI and FK209 were added after cooling. A battery was prepared.
  • FIG. 1 schematically shows the structure of the n-i-p-perovskite solar cell prepared in Comparative Examples and Preparation Examples of the present invention.
  • a solar cell was manufactured according to the Comparative Example and Preparation Example, and the current density-voltage (JV ) at 100 mA cm -2 , AM 1.5 G using a solar simulator (McScience, K3000 Lab solar cell IV measurement system, Class AAA). ) curves were measured. At this time, the light intensity was corrected using a Si reference electrode (certified by NREL) before the measurement, there was no light penetration before the potential scan, and the JV curve was reverse scan (short-circuited at forward bias 1.2 V). to 0 V) and forward scan (forward bias 0 V to short circuit 1.2 V). The step voltage was fixed at 100 mV.
  • the device of the comparative example exhibited a short circuit current density (J SC ) 26.04 mA cm -2 , an open circuit voltage (V OC ) 1.152 V, a charging factor (FF) of 78.13%, and a maximum PCE of 23.44% in an area of 0.0819 cm 2 , these characteristic values were comparable to those reported for the highest PCE of perovskite solar cells in the prior art.
  • both preparation devices using the fluorinated hole transport material according to the present invention showed almost identical (J SC ) values of 26.34 to 26.35 mA cm -2 and excellent V OC values of over 1.16 V. indicated.
  • the device using the spiro-mF of Preparation Example 1 exhibited a slightly higher FF (80.90%) than the other devices, and, as a result, showed the highest PCE of 24.82%.
  • spiro-TTBF and spiro-S a solar cell having a structure different from that of the preparation example was prepared, and at this time, the material of the comparative example (spiro-OMeTAD (2,2',7,7'-tetrakis[N, A solar cell using N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene) showed a low performance of 10% or less, while the same structure using spiro-TTBF and spiro-S It was confirmed that efficiencies as high as 10% or more can be achieved in solar cells.
  • a hole transport material maintaining excellent stability without deterioration even for a long period of time, and a solar cell having improved device performance such as PCE by including the hole transport material in a hole transport layer can be provided.

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  • Electromagnetism (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
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Abstract

La présente invention concerne un matériau de transport de trous pour une cellule solaire, et une cellule solaire le comprenant dans une couche de transport de trous, le matériau de transport de trous selon la présente invention présentant une performance améliorée d'un dispositif de cellule solaire comprenant un PCE, dure longtemps avant de se détériorer, et a une certaine stabilité, par rapport à un matériau de transport de trous de type spirobifluorène de l'état de la technique.
PCT/KR2020/017803 2020-02-21 2020-12-08 Matériau de transport de trous pour cellule solaire, et cellule solaire le comprenant WO2021167214A1 (fr)

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KR10-2020-0021577 2020-02-21
KR20200021577 2020-02-21
KR10-2020-0155579 2020-11-19
KR1020200155579A KR102491190B1 (ko) 2020-02-21 2020-11-19 태양 전지용 정공 수송 재료 및 이를 포함하는 태양 전지

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819457A (zh) * 2022-12-06 2023-03-21 厦门大学 一种含膦酸与甲硫基的咔唑类有机小分子空穴传输材料及其制备方法和应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070082226A1 (en) * 2005-10-07 2007-04-12 Au Optronics Corp. Organic light emitting diode and display device employing the same
KR20110116199A (ko) * 2009-02-02 2011-10-25 메르크 파텐트 게엠베하 금속 착물
US20150311440A1 (en) * 2014-04-28 2015-10-29 Korea Research Institute Of Chemical Technology Hole-transporting material for inorganic/organic hybrid perovskite solar cells
US20180122587A1 (en) * 2015-06-30 2018-05-03 Fujifilm Corporation Photoelectric conversion element, and solar cell using the same
WO2018079323A1 (fr) * 2016-10-24 2018-05-03 住友化学株式会社 Élément de conversion photoélectrique

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070082226A1 (en) * 2005-10-07 2007-04-12 Au Optronics Corp. Organic light emitting diode and display device employing the same
KR20110116199A (ko) * 2009-02-02 2011-10-25 메르크 파텐트 게엠베하 금속 착물
US20150311440A1 (en) * 2014-04-28 2015-10-29 Korea Research Institute Of Chemical Technology Hole-transporting material for inorganic/organic hybrid perovskite solar cells
US20180122587A1 (en) * 2015-06-30 2018-05-03 Fujifilm Corporation Photoelectric conversion element, and solar cell using the same
WO2018079323A1 (fr) * 2016-10-24 2018-05-03 住友化学株式会社 Élément de conversion photoélectrique

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819457A (zh) * 2022-12-06 2023-03-21 厦门大学 一种含膦酸与甲硫基的咔唑类有机小分子空穴传输材料及其制备方法和应用

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