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WO2020085579A1 - Nouveau composé spiro et dispositif électronique organique l'utilisant - Google Patents

Nouveau composé spiro et dispositif électronique organique l'utilisant Download PDF

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Publication number
WO2020085579A1
WO2020085579A1 PCT/KR2018/016936 KR2018016936W WO2020085579A1 WO 2020085579 A1 WO2020085579 A1 WO 2020085579A1 KR 2018016936 W KR2018016936 W KR 2018016936W WO 2020085579 A1 WO2020085579 A1 WO 2020085579A1
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organic
independently
compound
electronic device
alkyl
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Korean (ko)
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권순기
김윤희
최지영
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Gyeongsang National University GNU
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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
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/22—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 four or more hetero rings
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to novel spiro compounds and organic electronic devices using the same.
  • Typical examples of the organic electronic device include an organic light emitting device (OLED), an organic thin film transistor (OTFT), an organic optical sensor (OPD), an organic solar cell (OPV), a photodetector, a memory device, and a logic circuit.
  • OLED organic light emitting device
  • OFT organic thin film transistor
  • OPD organic optical sensor
  • OCV organic solar cell
  • photodetector a photodetector
  • memory device a logic circuit.
  • the organic solar cell uses an electron donor and an acceptor as a photoactive layer at the same time, and the film formation conditions are less demanding than conventional inorganic semiconductor devices.
  • Many studies have been conducted in recent years due to the advantage of being able to fabricate a flexible device that can be bent at will, especially the material of a layer.
  • the organic solar cell is composed of a junction structure of an electron donor and an electron acceptor, and is a very fast charge transfer phenomenon called a “photoinduced charge transfer (PICT)” between the electron donor and the electron acceptor, Research is being conducted to obtain a high-efficiency organic solar cell by increasing the photoexcitation charge transfer phenomenon.
  • PICT photoinduced charge transfer
  • PCBM ⁇ 6 ⁇ -1- (3- (methoxycarbonyl) propyl
  • a metanofullerene derivative published by Fred Wudl Group in 1995- ⁇ 5 ⁇ -1-phenyl [5,6] C61 ( ⁇ 6 ⁇ -1- (3- (methoxycarbonyl) propyl)- ⁇ 5 ⁇ -1-phenyl [5,6] C61)
  • perylene, 3,4,9,10-perylenetetracarboxylic acid diimide, phthalocyanine, and pentacene are used.
  • fullerene derivatives as well as fullerene derivatives represented by PCBM, have low solubility in organic solvents, when they are mixed with polymer compounds used as electron donors, there is a problem that phase separation occurs or overall overall efficiency is low. have. Moreover, solar absorption is weak and energy level manipulation is difficult.
  • the fullerene derivative As a replaceable compound of the fullerene derivative, it has excellent solubility in an organic solvent, high electron affinity similar to fullerene, excellent compatibility with an electron donor, high absorption coefficient for sunlight, and excellent photoelectric conversion efficiency. Research into compounds is needed.
  • the present invention aims to provide a novel spiro compound having an extended conjugated spiro structure.
  • An object of the present invention is to provide an organic electronic device having excellent light efficiency by employing the spiro compound of the present invention.
  • An object of the present invention is to provide an organic solar cell having excellent photoelectric conversion efficiency by employing the spiro compound of the present invention in a photoactive layer.
  • the present invention may include the following means.
  • the spiro compound according to an embodiment of the present invention is a small molecule compound of ADA composed of a central electron donor unit (D) and a terminal electron acceptor unit (A) on both sides of the central electron donor unit (D), and the central electron donor unit (D) )
  • ADA central electron donor unit
  • A terminal electron acceptor unit
  • the central electron donor unit (D) ) Has a spiro backbone, has a central skeleton extended to a two-dimensional region, and forms a delocalized pi-electron field along the central skeleton to have a more extended conjugated structure, represented by the following Chemical Formula 1 You can.
  • R 1 to R 4 are each independently C1-C30 alkyl
  • V 1 and V 2 are each independently a C6-C20 aromatic ring having methylidene as a linking group, and the aromatic rings are each independently C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylthio, halogen, cyano, HaloC1-C30alkyl, carboxyl, nitro, hydroxy and C1-C30alkyloxycarbonyl may be further substituted with one or more substituents selected from;
  • X 1 , X 2 , Y 1 and Y 2 are each independently O, S or Se.
  • the aromatic ring (V 1 and V 2 ) having the methylidene as a linkage group may be independently represented by the following formula (A).
  • Z 1 and Z 2 are each independently O, S, Se or CR 11 R 12 , and R 11 and R 12 are each independently halogen, cyano, carboxyl, nitro, hydroxy or C1-C30 alkyloxycarbonyl. ego;
  • A is a C6-C20 aromatic ring, and the aromatic ring may be further substituted with one or more substituents selected from C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylthio, halogen, cyano and halo C1-C30 alkyl.
  • the aromatic ring (V 1 and V 2 ) having the methylidene as a linkage group may be independently represented by the following formula (B).
  • R 11 and R 12 are each independently halogen, cyano, carboxyl, nitro, hydroxy or C1-C30 alkyloxycarbonyl;
  • R 21 to R 24 are each independently hydrogen, C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylthio, halogen, cyano or halo C1-C30 alkyl, or may be connected to adjacent substituents to form an aromatic ring. have.]
  • the spiro compound according to an embodiment of the present invention may be represented by the following Chemical Formula 2.
  • R 1 to R 4 are each independently C1-C30 alkyl
  • R 21 to R 24 are each independently hydrogen, C1-C30 alkyl, C1-C30 alkoxy, halogen or haloC1-C30 alkyl.
  • the present invention provides an organic electronic device including the spiro compound according to an embodiment of the present invention.
  • the organic electronic device may be an organic light emitting device, an organic thin film transistor, an organic photosensor or an organic solar cell, and preferably an organic solar cell.
  • the spiro compound may be included in the photoactive layer of the organic solar cell.
  • the spiro compound may be included in the photoactive layer of the organic solar cell as an electron acceptor.
  • the spiro compound of the present invention has a low bandgap, has excellent crystallization properties, and realizes effective intermolecular stacking of planar molecular sieves. Accordingly, the spiro compound of the present invention has a high absorption coefficient for sunlight and has an absorption spectrum of almost all wavelengths (eg, full color) in the visible region, and at the same time, has a more extended conjugated structure, thereby realizing high photoelectric conversion efficiency. have.
  • the spiro compound of the present invention has a high solubility in various organic solvents, and thus it is possible to manufacture an organic electronic device by a solution process, and it has high compatibility with an electron donor (for example, a polymer compound such as polythiophene). It is possible to increase the energy conversion efficiency of the electronic device.
  • an electron donor for example, a polymer compound such as polythiophene
  • the organic electronic device employing the spiro compound of the present invention has a high absorption coefficient and is capable of efficiently absorbing sunlight, and can realize excellent photoelectric conversion efficiency with high charge transfer characteristics.
  • the organic electronic device employing the spiro compound of the present invention as an electron acceptor can lower the driving voltage, improve light efficiency, and improve the life characteristics of the device by thermal stability of the compound.
  • the spiro compound of the present invention is used as a compound that can replace the fullerene derivative widely used as an electron acceptor, and can significantly improve the stability and photoelectric conversion efficiency of an organic solar cell. That is, the spiro compound of the present invention is very useful as a non-fullerene-based electron acceptor.
  • alkyl alkoxy
  • alkylthio alkyl moieties described herein include both straight-chain or ground forms.
  • alkoxy and alkylthio mean a monovalent organic radical represented by "* -O-alkyl” and "* -S-alkyl", respectively.
  • halogen means a fluorine, chlorine, bromine or iodine atom.
  • carboxyl described in this specification means a carboxylic acid group represented by * -COOH.
  • the present invention is a small molecule compound of ADA composed of a central electron donor unit (D) and a terminal electron acceptor unit (A) on both sides of the central electron donor unit (D), wherein the central electron donor unit (D) has a spiro backbone 2
  • the spiro compound of the present invention is represented by the following formula (1) Is displayed.
  • R 1 to R 4 are each independently C1-C30 alkyl
  • V 1 and V 2 are each independently a C6-C20 aromatic ring having methylidene as a linking group, and the aromatic rings are each independently C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylthio, halogen, cyano, HaloC1-C30alkyl, carboxyl, nitro, hydroxy and C1-C30alkyloxycarbonyl may be further substituted with one or more substituents selected from;
  • X 1 , X 2 , Y 1 and Y 2 are each independently O, S or Se.
  • the spiro compound of the present invention exhibits improved solubility in various organic solvents as it has a central electron donor unit (D) spiro backbone, and has excellent electron transport properties as an electron acceptor material in an organic solar cell, thereby exhibiting high efficiency and high efficiency. You can.
  • a compound having a central electron donor unit other than a spiro backbone must manufacture a device by a vacuum deposition method due to a considerably lowered solubility in an organic solvent, and the fabricated device exhibits a rapidly lowered photoelectric conversion efficiency.
  • the spiro compound of the present invention has a high absorption coefficient for sunlight, a high charge mobility, and a high solubility in an organic solvent, so that it is possible to manufacture an organic electronic device by a solution process, and the thermal stability of the organic electronic device including the same And improve the electrical properties. Moreover, it is possible to impart more advantage to the solution process because it satisfies the viscosity range favorable to the solution process with high solubility in a conventional organic solvent.
  • the spiro compound of the present invention has a high miscibility with an electron donor (eg, a polymer compound such as polythiophene), and thus can increase the efficiency of an organic electronic device including the same.
  • an electron donor eg, a polymer compound such as polythiophene
  • the spiro compound of the present invention is a structure in which an aromatic ring using methylidene as a linking group is introduced to form an extended conjugate out of the central skeleton to further improve the intermolecular interaction.
  • aromatic rings (V 1 and V 2 ) having the methylidene as a linking group may be independently represented by the following Chemical Formula A.
  • Z 1 and Z 2 are each independently O, S, Se or CR 11 R 12 , and R 11 and R 12 are each independently halogen, cyano, carboxyl, nitro, hydroxy or C1-C30 alkyloxycarbonyl. ego;
  • A is a C6-C20 aromatic ring, and the aromatic ring may be further substituted with one or more substituents selected from C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylthio, halogen, cyano and halo C1-C30 alkyl.
  • aromatic rings (V 1 and V 2 ) having the methylidene as a linking group may be independently represented by the following Chemical Formula B.
  • R 11 and R 12 are each independently halogen, cyano, carboxyl, nitro, hydroxy or C1-C30 alkyloxycarbonyl;
  • R 21 to R 24 are each independently hydrogen, C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylthio, halogen, cyano or halo C1-C30 alkyl, or may be connected to adjacent substituents to form an aromatic ring. have.]
  • the aromatic ring (V 1 and V 2 ) using the methylidene as a linking group may be selected from the following structures, but is not limited thereto.
  • the spiro compound according to an embodiment of the present invention minimizes the quenching of an excited state by an electromagnetic vibration (vibronic) path by the above-described structural characteristics, and thus has less energy loss due to absorption of sunlight and thus a higher absorption coefficient for sunlight. You can implement In addition, the compound has high crystallinity, and thus high charge mobility can be realized.
  • X 1 and X 2 are the same as each other, Y 1 and Y 2 may be the same as each other, more preferably X 1 , X 2 , Y 1 And Y 2 may all be S.
  • R 1 to R 4 are each independently C1-C30 alkyl
  • R 21 to R 24 are each independently hydrogen, C1-C30 alkyl, C1-C30 alkoxy, halogen or haloC1-C30 alkyl.
  • the spiro compound according to an embodiment of the present invention in terms of improving solubility as well as electron donation, it is preferable that at least one long-chain alkoxy is substituted in the central electron donor unit (D) spiro backbone.
  • R 1 to R 4 may each independently be C6-C30 alkyl, preferably crushed C6-C30 alkyl, and more preferably
  • A is an integer from 1 to 5
  • b and c are each independently an integer of 1 or more, and satisfies 2 ⁇ b + c ⁇ 20.
  • the spiro compound according to an embodiment of the present invention may be included in an organic electronic device, and among them, it is used as an electron acceptor material in a photoactive layer of an organic solar cell and replaces a fullerene derivative used in the prior art, thereby converting photoelectric conversion efficiency in an organic solar cell. It is possible to improve.
  • the spiro compound according to an embodiment of the present invention can be manufactured through a conventional organic synthesis method, and the organic solvent used therein is not limited, and the reaction time and temperature are also within the scope of the invention. Of course, changes are possible.
  • the present invention provides an organic electronic device comprising the spiro compound of the present invention.
  • the organic electronic device is not limited as long as the spiro compound of the present invention can be used, and in one non-limiting example, the organic electronic device is an organic solar cell, an organic thin film transistor, an organic memory, or Organic photoreceptors, organic photosensors, and the like, and preferably an organic solar cell or an organic thin film transistor.
  • the organic electronic device may be an organic solar cell, and the spiro compound may be included in the photoactive layer of the organic solar cell.
  • the spiro compound of the present invention is an electron acceptor used as an alternative compound of a fullerene derivative conventionally used in an organic solar cell, and the organic solar cell employing the same has improved photoelectric conversion efficiency.
  • the organic solar cell consists of a structure in which a hole transport layer and an electron transport layer are bonded, and when absorbing sunlight, electron-hole pairs are generated in the hole receptor and electrons move to the electron receptor to separate electron-holes. It shows the photoelectric conversion effect through the process.
  • the present invention can achieve a surprisingly improved photoelectric conversion efficiency by employing the spiro compound of the present invention in an organic solar cell.
  • the spiro compound of the present invention has high crystallinity and high charge mobility, so it can be used as an electron acceptor material in the photoactive layer of an organic solar cell, thereby realizing high efficiency.
  • the organic solar cell according to an embodiment of the present invention may include a substrate, a first electrode, a photoactive layer, and a second electrode, and of course, may further include a hole transport layer, an electron transport layer, and the like.
  • the organic solar cell according to an embodiment of the present invention may be an inverted type organic solar cell.
  • the substrate is PET (polyethylene terephthalate), PEN (polyethylene naphthelate), PP (polyperopylene), PI (polyimide), PC (polycarbornate), PS (polystylene), POM (polyoxyethlene), AS resin (acrylonitrile styrene) copolymer), ABS resin (acrylonitrile butadiene styrene copolymer) and TAC (Triacetyl cellulose).
  • PET polyethylene terephthalate
  • PEN polyethylene naphthelate
  • PP polyperopylene
  • PI polyimide
  • PC polycarbornate
  • PS polystylene
  • POM polyoxyethlene
  • AS resin acrylonitrile styrene copolymer
  • ABS resin acrylonitrile butadiene styrene copolymer
  • TAC Triacetyl cellulose
  • the first electrode is formed by applying a transparent electrode material to one surface of the substrate or coated in a film form using sputtering, E-Beam, thermal evaporation, spin coating, screen printing, inkjet printing, doctor blade or gravure printing. do.
  • the first electrode is a part that functions as an anode.
  • any material having transparency and conductivity may be used.
  • ITO indium tin oxide
  • FTO fluorine doped tin oxide
  • AZO aluminum doped zinc oxide
  • IZO indium zink oxide
  • ITO indium tin oxide
  • gold, silver, and fluorine doped tin oxide FTO
  • FTO fluorine doped tin oxide
  • AZO aluminum doped zinc oxide
  • IZO indium zink oxide
  • ZnO-Ga 2 O 3 ZnO-Al 2 O 3
  • ATO antimony tin oxide, SnO 2 -Sb 2 O 3
  • the spiro compound may be included in the photoactive layer, and the compounding amount thereof may be appropriately adjusted according to the application.
  • the spiro compound since the spiro compound has excellent solubility, it can be dissolved in an organic solvent and used as an electron acceptor material of a photoactive layer with a thickness of 60 mm or more, preferably 60 to 120 nm.
  • an example of an electron donor is PBDTTT-CT (Poly ⁇ [4,8-bis- (2-ethyl-hexyl-thiophene-5-yl) -benzo [1,2-b: 4,5-b '] dithiophene -2,6-diyl] -alt- [2- (2'-ethyl-hexanoyl) -thieno [3,4-b] thiophen-4,6-diyl] ⁇ ), PBDTTT-CF (Poly [1- ( 6- ⁇ 4,8-bis [(2-ethylhexyl) oxy] -6-methylbenzo [1,2- b : 4,5- b ′] dithiophen-2-yl ⁇ -3-fluoro-4-methylthieno [3 , 4- b ] thiophen-2-yl) -1-octanone]), P3HT (Poly (3-hexylthiophene)), PCDTBT (Poly [
  • the electron donor and the spiro compound are mixed in a weight ratio of 1: 0.5 to 1: 4 to form a photoactive layer by a solution process method such as spin coating, spray coating, screen printing, doctor blade method, and the like, and dissolving the solution in an organic solvent.
  • a solution process method such as spin coating, spray coating, screen printing, doctor blade method, and the like, and dissolving the solution in an organic solvent.
  • the organic solvent may be acetone, methanol, THF, toluene, xylene, tetralin, chloroform, chlorobenzene, dichlorobenzene, or a mixed solvent thereof, but is not limited thereto.
  • the photoactive layer containing the spiro compound according to the present invention increases the photoelectric conversion efficiency by increasing short circuit current density and open circuit voltage due to high electron density.
  • the second electrode may be deposited using a thermal evaporator while the electron transport layer is introduced.
  • the usable electrode materials include lithium fluoride / aluminum, lithium fluoride / calcium / aluminum, aluminum / calcium, barium fluoride / aluminum, barium fluoride / barium / aluminum, barium / aluminum, aluminum, gold, silver, magnesium: silver and It may be selected from lithium: aluminum, and preferably, an electrode made of silver, aluminum, aluminum / calcium or barium fluoride / barium / aluminum is used.
  • materials of the electron transport layer and the hole transport layer may be used unlike the electron transport layer and the hole transport layer of the general type.
  • the electron transport layer material include TiO x , ZnO, TiO 2 , ZrO 2 , MgO, and HfO 2
  • examples of the hole transport layer material include NiO, Ta 2 O 3 , MoO 3 , and Ru 2 O 3 And metal oxides.
  • Trimethyl (thieno [3,2-b] thiophen-2-yl) silane (2.74 g, 12.9 mmol) was added to THF (200 mL) and dissolved in a nitrogen-substituted three-necked flask, the temperature was lowered to -78 ° C, and 2.5. M n-Butyllithium (5.2 mL, 12.9 mmol) was dropped and stirred for 2 hours. And, after dissolving ZnCl 2 (1.76 g, 12.9 mmol) in THF (30 mL), the temperature was raised to -40 ° C, and slowly dropped and stirred at 0 ° C for 1 hour.
  • ITO Indium Tin Oxide
  • first electrode an anode transparent electrode
  • IPA isopropyl alcohol
  • the ITO glass substrate washed as described above was subjected to ultraviolet / ozone treatment for 15 minutes, followed by spin coating ZnO ⁇ NPs having a thickness of 30 nm on the ITO substrate. And the substrate coated with ZnO ⁇ NPs was heat treated at 100 ° C. for 10 minutes on a hot plate.
  • the photoactive layer was prepared by dissolving Compound 1 (electroreceptor) and P3HT (Poly (3-hexylthiophene)) (electron donor) prepared in Example 1 in a chloroform solvent at a ratio of 1: 1 by weight, and carrying a 0.45 ⁇ m (PTFE) syringe.
  • An organic semiconductor solution filtered through a filter (syringe filter) was prepared by coating on a ZnO layer with a thickness of 100 nm through a spin coating method.
  • An organic solar cell was fabricated by depositing a 10 nm thick MoO 3 and 100 nm thick Ag electrode as a top electrode on the photoactive layer under a 3 ⁇ 10 ⁇ 6 torr vacuum in a thermal evaporator.
  • An organic solar cell was produced in the same manner as in Example 5, except that Compound 2 prepared in Example 2 was used as the electron acceptor, and its properties were confirmed.
  • An organic solar cell was manufactured in the same manner as in Example 5, except that Compound 3 prepared in Example 3 was used as the electron acceptor, and its properties were confirmed.
  • An organic solar cell was manufactured in the same manner as in Example 5, except that Compound 4 prepared in Example 4 was used as the electron acceptor, and its properties were confirmed.
  • An organic solar cell was prepared in the same manner as in Example 5 using a conventional electron acceptor (PC71BM) instead of Compound 1 to compare its properties.
  • PC71BM conventional electron acceptor
  • An organic solar cell was prepared in the same manner as in Example 5 using Comparative Compound C1 instead of Compound 1 to compare its properties.
  • An organic solar cell was prepared in the same manner as in Example 5 using Comparative Compound C2 instead of Compound 1 to compare its properties.
  • An organic solar cell was prepared in the same manner as in Example 5 using Comparative Compound C3 instead of Compound 1 to compare its properties.
  • V oc (V) and J sc (mA / cm 2 ) each represent a voltage value when the current is 0 and a current value when the voltage is 0, in the current-voltage curve of the fabricated device.
  • the fill factor (FF) is calculated from Equation 1 below.
  • V mpp and J mpp each represents the voltage and current value at the point indicating the maximum power when measuring the current-voltage of the fabricated device
  • V oc (V) and J sc (mA / cm 2 ) Each represents the voltage value when the current is 0 and the current value when the voltage is 0 in the current-voltage curve of the fabricated device.
  • Equation 2 FF, V oc and J sc are as defined in Equation 1, and P in represents the total energy of light incident on the device.
  • the spiro compound of the present invention is used as a replacement compound of a conventional fullerene derivative, and has high electron affinity and excellent compatibility with an electron donor, thereby having high photoelectric conversion efficiency.

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  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Photovoltaic Devices (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne un nouveau composé spiro et un dispositif électronique organique l'utilisant et, plus particulièrement, un nouveau composé spiro ayant une structure spiro conjuguée étendue, et un dispositif électronique organique ayant un excellent rendement lumineux du fait de l'utilisation du nouveau composé spiro.
PCT/KR2018/016936 2018-10-22 2018-12-28 Nouveau composé spiro et dispositif électronique organique l'utilisant Ceased WO2020085579A1 (fr)

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WO2013159863A1 (fr) * 2012-04-25 2013-10-31 Merck Patent Gmbh Polymères conjugués
KR102295781B1 (ko) * 2018-10-12 2021-09-01 경상국립대학교산학협력단 신규한 화합물 및 이를 이용하는 유기 전자 소자

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KR20120069675A (ko) * 2009-08-05 2012-06-28 캠브리지 디스플레이 테크놀로지 리미티드 유기 반도체
CN105315298A (zh) * 2014-08-04 2016-02-10 中国科学院化学研究所 基于七并稠环单元的a-d-a共轭分子及其制备方法和应用
WO2017191466A1 (fr) * 2016-05-06 2017-11-09 Imperial Innovations Limited Mélanges ternaires organiques
WO2018103496A1 (fr) * 2016-12-07 2018-06-14 北京大学 Macromolécule conjuguée polycyclique et procédé pour sa fabrication et application de celle-ci
KR20180104398A (ko) * 2017-03-13 2018-09-21 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 전자 소자

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