WO2019164054A1 - Nouveau composé, procédé de fabrication de celui-ci et élément électronique organique l'utilisant - Google Patents

Nouveau composé, procédé de fabrication de celui-ci et élément électronique organique l'utilisant Download PDF

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Publication number
WO2019164054A1
WO2019164054A1 PCT/KR2018/004224 KR2018004224W WO2019164054A1 WO 2019164054 A1 WO2019164054 A1 WO 2019164054A1 KR 2018004224 W KR2018004224 W KR 2018004224W WO 2019164054 A1 WO2019164054 A1 WO 2019164054A1
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WIPO (PCT)
Prior art keywords
independently
alkyl
compound
integer
alkoxy
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PCT/KR2018/004224
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English (en)
Korean (ko)
Inventor
이종철
신원석
이상규
이행근
송창은
문상진
Original Assignee
한국화학연구원
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Publication of WO2019164054A1 publication Critical patent/WO2019164054A1/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
    • H10K30/50—Photovoltaic [PV] devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • H01L2031/0344—Organic materials
    • 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 novel organic semiconductor compound, a preparation method thereof and an organic electronic device using the same.
  • Organic semiconductor compounds are applied to a wide range of devices or devices, including, for example, organic solar cells (OPVs), organic field effect transistors (OFETs), organic light emitting diodes (OLEDs), photodetectors, sensors, memory devices, logic circuits, and the like. have.
  • OLEDs organic solar cells
  • OFETs organic field effect transistors
  • OLEDs organic light emitting diodes
  • photodetectors sensors, memory devices, logic circuits, and the like.
  • the organic solar cell is a device that uses a donor material (electron donor) and an acceptor material (electron acceptor) together as a photoactive layer.
  • the organic solar cell is not difficult to form a film compared to a conventional inorganic semiconductor compound, and has a thin thickness of several hundred nm or less. It is possible to construct the photoactive layer at a relatively low cost. In particular, in the case of using the organic semiconductor compound, a lot of research has recently been progressed due to the advantage that the flexible device can be bent at will.
  • the efficiency of the organic solar cell is determined by the open circuit voltage (Voc), the short-circuit current (Jsc), and the fill factor (FF).
  • the open voltage is determined by the energy levels of the donor and acceptor materials, and the short-circuit current is closely related to the absorption spectra of the donor and acceptor materials that absorb light.
  • the fill factor is also determined by the morphology of the mixed film of the donor material and the acceptor material. Accordingly, research on optical characteristics and electro-optical characteristics of a photovoltaic device is required according to the change of the structure of the donor material to increase the efficiency of the organic solar cell.
  • donor materials used in organic solar cells can be classified into polymer materials and monomolecular materials.
  • monomolecular materials purity can be improved compared to polymer materials, and compared to polymer materials in reproducing synthesis and mass production. It is characterized by ease, but due to the problem of falling compared to the polymer material in film film formation, the disadvantage of the fill factor is worse than the polymer material.
  • Still another object of the present invention is to provide an organic photoelectric conversion material and an organic electronic device including the compound, specifically, the compound as an electron donor and having a high energy conversion efficiency.
  • Z 1 and Z 2 are each independently O, S or Se;
  • R 1 and R 2 are each independently C 1 -C 30 alkyl, C 1 -C 30 alkoxy, C 1 -C 30 alkylthio, C 6 -C 30 aryl or C 3 -C 30 heteroaryl, said aryl or Heteroaryls may each be further substituted with one or more substituents independently selected from C 1 -C 30 alkyl, C 1 -C 30 alkoxy and C 1 -C 30 alkylthio;
  • A is each independently C 6 -C 30 arylene or C 3 -C 30 heteroarylene, and the arylene or heteroarylene is each independently C 1 -C 30 alkyl, C 1 -C 30 alkoxy, C 1 May be further substituted with one or more substituents selected from -C 30 alkylthio, haloC 1 -C 30 alkyl, C 1 -C 30 alkoxycarbonyl, halogen and cyano;
  • Y 1 and Y 2 are each independently O or S;
  • Each R 3 is independently halogen
  • n are each independently an integer of 1 to 4, and when n is an integer of 2 or more, the R 3 may be the same or different from each other;
  • n is an integer from 1 to 5;
  • a method for preparing a compound represented by the following formula (1) comprising the step of reacting a dicarbaldehyde compound of formula (A) and a phosphorus compound of formula (B).
  • R 1 and R 2 are each independently C 1 -C 30 alkyl, C 1 -C 30 alkoxy, C 1 -C 30 alkylthio, C 6 -C 30 aryl or C 3 -C 30 heteroaryl, said aryl or Heteroaryls may each be further substituted with one or more substituents independently selected from C 1 -C 30 alkyl, C 1 -C 30 alkoxy and C 1 -C 30 alkylthio;
  • A is each independently C 6 -C 30 arylene or C 3 -C 30 heteroarylene, and the arylene or heteroarylene is each independently C 1 -C 30 alkyl, C 1 -C 30 alkoxy, C 1 May be further substituted with one or more substituents selected from -C 30 alkylthio, halo C 1 -C 30 alkyl, C 1 -C 30 alkoxycarbonyl, halogen and cyano;
  • Y 1 and Y 2 are each independently O or S;
  • Each R 3 is independently halogen
  • Each R 3 is independently halogen
  • the compound of Formula 1 may include a linking group having at least two monocyclic aromatic rings (substituent A of Formula 1) or a linking group including a polycyclic aromatic ring.
  • the repeating aromatic rings may have different or different substituents from each other.
  • the compound according to an embodiment of the present invention when the repeating unit of the central skeleton is 1, it exhibits excellent light stability and long-term stability with high compatibility with the electron acceptor, giving excellent life characteristics.
  • the compound according to an embodiment of the present invention may be specifically selected from the following structures, but is not limited thereto.
  • Z 1 and Z 2 are each independently O, S or Se;
  • R 1 and R 2 are each independently C 1 -C 30 alkyl, C 1 -C 30 alkoxy, C 6 -C 30 aryl or C 3 -C 30 heteroaryl, wherein the aryl or heteroaryl are each independently C 1 May be further substituted with one or more substituents selected from -C 30 alkyl, C 1 -C 30 alkoxy and C 1 -C 30 alkylthio;
  • A is each independently C 6 -C 30 arylene or C 3 -C 30 heteroarylene, and the arylene or heteroarylene is each independently C 1 -C 30 alkyl, C 1 -C 30 alkoxy, C 1 May be further substituted with one or more substituents selected from -C 30 alkylthio, haloC 1 -C 30 alkyl, C 1 -C 30 alkoxycarbonyl, halogen and cyano;
  • Y 1 and Y 2 are each independently O or S;
  • Each R 3 is independently halogen
  • n are each independently an integer of 1 to 4, and when n is an integer of 2 or more, the R 3 may be the same or different from each other;
  • n is an integer from 1 to 5;
  • the compounds of the present invention are easy to manufacture in high yield and high purity by the simple process described above, and thus are highly industrially available.
  • the present invention provides an organic photoelectric conversion material comprising the compound of formula (1).
  • the compound of formula 1 has a maximum absorption wavelength in the 400 to 700 nm range showing the highest energy intensity in the solar spectrum.
  • the organic photoelectric conversion material according to the exemplary embodiment of the present invention may be applied to a photovoltaic device, an organic light emitting diode, an organic thin film transistor, or the like.
  • the present invention provides an organic electronic device comprising a compound of formula (1).
  • the organic electronic device according to an embodiment of the present invention may be an organic solar cell.
  • the organic solar cell according to the present invention may include a substrate, a first electrode, a buffer layer, a photoactive layer and a second electrode.
  • the substrate is preferably a transparent material, for example, glass; Or plastics such as polyethylene terephthalate (PET), polyethylene naphthelate (PEN), polypropylene (PP), polyamide (PI), and triacetyl cellulose (TAC).
  • PET polyethylene terephthalate
  • PEN polyethylene naphthelate
  • PP polypropylene
  • PI polyamide
  • TAC triacetyl cellulose
  • the first electrode is formed on one surface of the substrate by applying a transparent material or coating in the form of a film using a method such as sputtering or spin coating.
  • the first electrode functions as an anode, and a material having transparency and conductivity is used as a material having a lower work function than the second electrode described later.
  • ITO indium-tin oxide
  • FTO fluorine doped tin oxide
  • ZnO- Ga 2 O 3 or Al 2 O 3
  • SnO 2 -Sb 2 O 3 or the like may be used.
  • the buffer layer formed on the first electrode may include PEDOT: PSS (poly (3,4-ethylenedioxythiophene) doped with polystyrenesulfonate) to improve charge mobility.
  • the buffer layer may be introduced through a method such as spin coating, but is not limited thereto.
  • the photoactive layer is formed on the buffer layer.
  • the photoactive layer may be formed of a compound using the compound of the present invention as an electron donor and using a single molecule selected from C 60 fullerene, C 70 fullerene derivative and a non fullerene derivative as an electron acceptor.
  • the compound of the present invention and a C 60 fullerene derivative or a C 70 fullerene derivative are combined, they are prepared by dissolving them in a single organic solvent or two or more organic solvents having different boiling points, wherein the organic solvent is chlorobenzene, 1,2-dichloro. Benzene, chloroform and the like may be used, and the organic solvent may be prepared so as to contain a solid content of 1.0 to 5.0% by weight.
  • the ratio may be specifically blended in a weight ratio of 1: 0.5 to 1: 4, and more specifically in a weight ratio of 1: 1 to 1: 2. It is good to be combined.
  • the solution in which the electron donor (compound of the present invention) and the electron acceptor are dissolved is applied or coated by a method such as an inkjet printing method, a spin coating method, a screen printing method, a doctor blade method, or the like, and about 70 nm or more, preferably 80 to 80 nm. A 300 nm thick photoactive layer is formed.
  • the second electrode acts as a cathode, and gold, aluminum, copper, silver or alloys thereof (calcium / aluminum alloy, magnesium / silver alloy, aluminum / lithium alloy, etc.) may be used.
  • the organic solar cell according to the exemplary embodiment of the present invention may be a stacked organic solar cell including two or more photoactive layers having different absorptions. This absorbs the necessary area for each layer, thereby achieving higher efficiency than a single layer organic solar cell.
  • Benzodithiophene (1) (5 g, 6.82 mmol) was dissolved in 60 mL of THF and the temperature was lowered to -78 ° C and n-butyllithium (3.8 ml, 6.14 mmol, 1.6 M solution in Hexane) was slowly added. After stirring at ⁇ 78 ° C. for 1 hour, 1,2-dioodoethane (1.92 g, 6.82 mmol) was added while maintaining ⁇ 78 ° C. After further stirring at room temperature (23 ° C.) for 15 hours, methanol was added to the reaction solution to terminate the reaction. The solvent was distilled under reduced pressure and the residue was separated by column chromatography to obtain the title compound (2) (4.7 g, 80%). Got it.
  • Triethylamine (0.1 mL) was added to a dichloroethane (10 mL) solution in which compound (6) (0.267 g, 0.11 mmol) and 3-chloroindandione (0.1 g, 0.56 mmol) were dissolved, followed by argon atmosphere. Stir at room temperature for 13 hours. Dropping the reaction solution in methanol (20 mL) to form a precipitate, and the resulting precipitate was filtered and dissolved again with a minimum amount of chloroform and again precipitated with hexane to give Compound 1 (0.25 g, 81%).
  • Triethylamine (0.1 mL) in dichloroethane (5 mL) solution of compound 10 (0.108 g, 0.062 mmol) and 3-fluoroindandione (compound (11), 0.81 g, 0.49 mmol). ) was added and stirred at room temperature for 13 hours under an argon atmosphere. Dropping the reaction solution in methanol (20 mL) gave a precipitate, and the resulting precipitate was filtered and dissolved again with a minimum amount of chloroform and again precipitated with hexane to give the title compound 2 (63 mg, 50%).
  • the organic solar cell employing the compound according to the present invention has a high efficiency by affecting the rise of all factors such as the open voltage, current, fill factor affecting the energy conversion efficiency (photoelectric conversion efficiency) It can be seen that the result of.
  • the organic solar cell employing the compound according to the present invention implements an energy conversion efficiency of up to 10.25%.
  • the organic solar cell has a fill factor value of 70% or more.
  • the compound according to the present invention can be usefully used as an organic photoelectric conversion material that can implement a high efficiency with an excellently improved charge mobility.
  • the compound according to the present invention is expected to be highly commercially available, as it is confirmed that the structure is easy for the solution process.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Computer Hardware Design (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Photovoltaic Devices (AREA)

Abstract

La présente invention concerne un nouveau composé semi-conducteur organique, un procédé de fabrication de celui-ci et un élément électronique organique l'utilisant. Le nouveau composé semi-conducteur organique selon la présente invention a un groupe fonctionnel indane substitué par halo introduit dans un réseau central particulier, et peut ainsi améliorer de manière significative les caractéristiques optiques de l'élément électronique organique le comprenant.
PCT/KR2018/004224 2018-02-26 2018-04-11 Nouveau composé, procédé de fabrication de celui-ci et élément électronique organique l'utilisant WO2019164054A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2018-0023195 2018-02-26
KR1020180023195A KR102114177B1 (ko) 2018-02-26 2018-02-26 신규한 화합물, 이의 제조방법 및 이를 이용하는 유기 전자 소자

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Cited By (1)

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CN112159418A (zh) * 2020-09-11 2021-01-01 中国科学院宁波材料技术与工程研究所 共轭有机分子及有机太阳能电池

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CN114539290B (zh) * 2020-11-25 2023-09-05 中国科学院宁波材料技术与工程研究所 共轭有机分子及其制备方法和应用

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WO2018032945A1 (fr) * 2016-08-17 2018-02-22 国家纳米科学中心 Composé photoélectrique contenant une modification du benzothiophène (benzosélénophène), son procédé de préparation et son utilisation

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WO2016120166A1 (fr) * 2015-01-27 2016-08-04 Sony Corporation Molécules à base de squaraïne comme matériau pour couches organiques de conversion photoélectrique dans des photodiodes organiques
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WO2018032945A1 (fr) * 2016-08-17 2018-02-22 国家纳米科学中心 Composé photoélectrique contenant une modification du benzothiophène (benzosélénophène), son procédé de préparation et son utilisation

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Publication number Priority date Publication date Assignee Title
CN112159418A (zh) * 2020-09-11 2021-01-01 中国科学院宁波材料技术与工程研究所 共轭有机分子及有机太阳能电池
CN112159418B (zh) * 2020-09-11 2024-04-05 中国科学院宁波材料技术与工程研究所 共轭有机分子及有机太阳能电池

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KR102114177B1 (ko) 2020-05-22

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