WO2015000265A1 - Matériau moléculaire de couche tampon de cathode soluble dans des alcools contenant trois groupes oxyde d'arylphosphine et un groupe fonctionnel azacyclo et procédé de synthèse et son application - Google Patents

Matériau moléculaire de couche tampon de cathode soluble dans des alcools contenant trois groupes oxyde d'arylphosphine et un groupe fonctionnel azacyclo et procédé de synthèse et son application Download PDF

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Publication number
WO2015000265A1
WO2015000265A1 PCT/CN2013/089024 CN2013089024W WO2015000265A1 WO 2015000265 A1 WO2015000265 A1 WO 2015000265A1 CN 2013089024 W CN2013089024 W CN 2013089024W WO 2015000265 A1 WO2015000265 A1 WO 2015000265A1
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cathode buffer
buffer layer
reaction
palladium
target product
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Chinese (zh)
Inventor
朱旭辉
谭婉怡
魏鑫峰
李敏
彭俊彪
曹镛
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South China University of Technology SCUT
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South China University of Technology SCUT
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
    • C07F9/6539—Five-membered rings
    • C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • 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 invention relates to a cathode buffer layer material, in particular to a kind of alcohol-soluble cathode buffer layer molecular type material containing a triarylphosphine oxide and a nitrogen heterocyclic functional group, and a synthesis method and application thereof.
  • Efficient electron injection or collection is critical to achieving high performance organic light-emitting diodes, organic field-effect transistors and organic light-emitting field effect transistors, and optoelectronic devices such as organic photovoltaics.
  • organic light-emitting diodes organic field-effect transistors and organic light-emitting field effect transistors, and optoelectronic devices such as organic photovoltaics.
  • metal or metal oxides with high environmental stability as cathode materials such as Al, Ag, Au, ITO, etc.
  • the latter has a higher work function, so it is particularly urgent to design and synthesize cathode buffer materials that match them to improve electron injection or collection performance.
  • the cathode interface materials such as LiF and CsF were mainly used to realize electron injection or collection of electrons from the aluminum metal cathode, but these materials were formed by vacuum evaporation.
  • Full solution processing optoelectronic devices offer the potential to achieve low cost, large area, flexible organic optoelectronic devices. Therefore, it is important to prepare a solution-processable cathode buffer material.
  • the introduction of the phosphorus oxygen group is advantageous for improving the alcohol solubility, film morphology stability and electron injection performance of the molecule.
  • the material disclosed in the present invention introduces an electron-withdrawing nitrogen heterocycle to further improve electron injection, transport properties and hole blocking properties, thereby simplifying the structure of the organic electroluminescent device and promoting device stability.
  • the cathode buffer material can effectively assist in the injection/transportation or collection of electrons from metal or metal oxide electrodes such as Al, Ag, Au, ITO, etc.; due to lithium ion, potassium ion, barium ion, calcium ion
  • the cathode buffer layer material may be doped with an inorganic or organic salt containing these ions to form a doped or composite cathode buffer layer to improve device performance.
  • the object of the present invention is to provide a class of alcohol-soluble cathode buffer layer molecular type materials containing a triarylphosphine oxide and a nitrogen heterocyclic functional group in view of the prior art disadvantages.
  • An alcohol-soluble cathode buffer layer molecular material containing a triarylphosphine oxide and a nitrogen heterocyclic functional group which is characterized by having one of the following chemical structural formulas:
  • R44 and R45 are selected from an alkyl chain or an alkoxy chain having 1 to 18 carbon atoms or are any of the following structural units:
  • R46 and 7 are an indenyl chain having a carbon number of 1 to 18; and the R 2 is any one of the following structural units:
  • Diphenylphosphine chloride is used as a reaction raw material, and is introduced into a group by a reaction of n-butyllithium at -78 ° C to obtain an unoxidized target product containing bromine, wherein, when it contains ⁇ 1 43 , it is catalyzed by palladium.
  • the coupling reaction introduces an aryl group or a fused ring aryl group; when R contains 4 and R 45 , the fluorenone is catalyzed to introduce an aryl group or a fused ring aryl group by methanesulfonic acid, or the ruthenium is catalyzed by potassium hydroxide.
  • the boronic acid ester-containing target product obtained in the step 3) is coupled with the group R 2 by a palladium-catalyzed coupling reaction to obtain a target product, wherein when R 2 contains R 48 or R 5Q , it is passed through t-butanol.
  • Potassium benzotriazole is catalytically introduced into an alkyl or alkoxy chain having a carbon number of 1 to 18; for the case where 9 is contained in R 2 , the alkyl group having a carbon number of 1 to 18 is catalytically introduced by aluminum trichloride Base chain or alkoxy chain.
  • a boronic acid ester group is introduced into the phosphoryloxy group by a palladium catalyzed reaction, and the palladium catalyzes the reaction: the reactant is under the protection of an inert gas, and the reaction temperature range is 80-100 ° C, the reaction time range is 2-12 hours, using 1,1 '-bisdiphenylphosphinoferrocene palladium dichloride as a catalyst for the reaction; Step 4) by palladium-catalyzed coupling reaction will!
  • the palladium catalyzed coupling reaction the reactant is under the protection of an inert gas, the reaction temperature is in the range of 70-110 ° C, and the reaction time is in the range of 8-36 hours, using four ( Triphenylphosphine) Palladium or a reaction using palladium acetate and a tricyclohexylphosphine system as a catalyst.
  • the cathode buffer material in electroluminescent display, illumination, and organic photovoltaic cell devices. Compared with the prior art, the present invention has the following advantages and benefits:
  • the new cathode buffer layer molecular type material has good alcohol solubility.
  • the new cathode buffer layer molecular material has good film morphology stability.
  • the novel cathode buffer layer molecular material has better electron injection, transport and hole blocking properties, and the device performance can be improved while simplifying the structure of the organic electroluminescent device.
  • the new cathode buffer layer molecular material can effectively assist the injection/transport or collection of electrons from metal or metal oxide electrodes such as Al, Ag, Au, ITO.
  • the new cathode buffer layer molecular material can interact with lithium ions, potassium ions, strontium ions, calcium ions, etc., so the cathode buffer layer material can be combined with inorganic salts or organic salts containing these ions. Doping, forming a doped or composite cathode buffer layer, improves device performance.
  • Figures la and lb are differential scanning calorimetry curves for the novel cathode buffer materials 1 and 2.
  • 2 is a current density-voltage curve of an organic electroluminescent device in which the cathode is a novel cathode buffer material 1/A1, material 1: barium carbonate/Al, material 2/ ⁇ 1, ion salt/Al, A1, respectively.
  • Figure 3 shows the current density-voltage curves of organic photovoltaic cell devices with cathodes 1/Ag and ethanol/Ag, respectively.
  • 1,1 '-bisdiphenylphosphinoferrocene dichloride palladium C80 mg, 0.11 mmol was added to the compound (4) (1.35 g, 3.32 mmol), dipentyl diboron under N 2 atmosphere. 1.26 g, 4.98 mmol), a mixture of potassium acetate (977 mg, 9.95 mmol) and 1,4-dioxane (30 mL). The reaction was heated to 80 ° C and allowed to react for 3 hours. After cooling to room temperature and removing the solvent under reduced pressure, the reaction mixture was poured into water and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated.
  • Tetrakis(triphenylphosphine)palladium (23 mg, 0.02 mmol) was added to compound 5 (331 mg, 0.73 mmol), 4,7-dibromo-2,1,3-benzothiazide under N 2 atmosphere.
  • DSC Differential Scanning Calorimetry
  • cathode buffer materials 1 and 2 were selected as cathode buffer materials, and material 1 was doped with cesium carbonate (Cs 2 C0 3 ); ionic salts were used ( Liu et al Chem. Asian J. 2012, 7, 2126-2132, Compound 2) as cathode buffer material for comparison; using laboratory existing green light molecular material (Chinese Patent Application No.: 200810218649.5) as luminescent material, device
  • Cs 2 C0 3 cesium carbonate
  • ITO Indium tin oxide
  • a PEDOT:PSS Bayer AG film having a thickness of about 40 nm was spin-coated, and the substrate was dried in a vacuum oven at 80 ° C for 8 hours to remove the solvent.
  • a p-xylene solution of a light-emitting layer (green material, 45 nm) was spin-coated on a PEDOT:PSS layer in a nitrogen atmosphere glove box (Vacuum Atmosphere Co.) and dried at 100 ° C for 10 minutes.
  • the new cathode buffer materials 1 and 2 of the ethanol solution are spin-coated on the light-emitting layer, dried at 80 ° C for 10 minutes; or the material 1 and Cs 2 C0 3 doped (4: 1, ⁇ : ⁇ ) in ethanol solution It is coated on the luminescent layer and dried at 80 ° C for 10 minutes; or a solution of the ionic salt in methanol is spin-coated on the luminescent layer.
  • a metal Al (120 nm) cathode was vapor-deposited under a vacuum of 3 x 10 _ 4 Pa.
  • the effective illuminating area of the device is 0.165 cm 2 .
  • Film thickness was measured using a Veeco Dektakl 50 step meter.
  • the deposition rate of the metal electrode evaporation and its thickness were measured using a Sycon Instrument thickness/speed meter STM-100. Except that the spin coating process of the PEDOT:PSS film was completed in the atmosphere, all other steps were completed in a glove box in a nitrogen atmosphere.
  • the concentration of the new cathodic buffer material 1 and 2 for spin coating is 6 mg/mL, and the rotation speed is 2000 r/min.
  • the concentration of material 1 in the solution for material 1 and Cs 2 C0 3 doping spin coating is 6 mg/ mL, the speed is 2000 r/min; the concentration of the solution for ion salt spin coating is 2 mg/mL, and the rotation speed is 2000 r/min.
  • the device structure is as follows:
  • ITO/PEDOT PSS/Green Light Material / Material 1/A1
  • ITO/PEDOT PSS/green material/material 1: Cs 2 C0 3 /Al
  • ITO/PEDOT PSS/Green Light Material / Material 2/A1
  • ITO/PEDOT PSS/Green Light Material / Ion Salt /A1
  • ITO/PEDOT PSS/Green Light Material / A1
  • the organic electroluminescent device prepared by the spin coating method uses a cathode buffer layer material, and the ignition voltage is remarkably lowered, indicating that the electron injecting performance is good, and the current efficiency is greatly improved.
  • the new Cathode Cushioning Materials 1 and 2 better improve the electroluminescence properties compared to the ionic salts (as shown in Table 1 and Figure 2). For example, in the organic electroluminescent device, reduce the current density, showed enhanced hole-blocking ability, respectively, so the maximum current efficiency of 4.2 cd A- 1 B 4.5 cd A- Wo is 1.6 times when using ionic salt. After the new cathode buffer material 1 is doped with Cs 2 C0 3 , the device performance is significantly improved.
  • the maximum current efficiency is 8.2 cd A- 1 , which is 2.0 times that of material 1, indicating that material 1 is doped with cesium carbonate to form a doped or composite cathode buffer layer to improve device performance.
  • the data in Table 1 shows that the use of a new cathode buffer material, with a small efficiency roll-off, is conducive to the improvement of device stability.
  • Table 1: The cathode is a new type of cathode buffer material 1/A1, material l: Cs 2 C0 3 /Al, material 2/ ⁇ 1, ion salt/Al,
  • a new cathode buffer layer material 1 is selected as the cathode buffer layer material; DPP (TBFu) 2 ⁇ Adv. Funct. Mater. 2009, 19, 3063-3069) is used for the organic photovoltaic cell Body Material, PC 61 BM is the acceptor material of organic photovoltaic cells.
  • the detailed preparation process of the device is as follows: Indium tin oxide (ITO) conductive glass substrate with resistance of 10-20 ⁇ / ⁇ is sequentially passed through deionized water, acetone, detergent Ultrasonic cleaning with deionized water and isopropanol. After drying in an oven, treat with PLASMA (oxygen plasma) for 4 minutes.
  • ITO Indium tin oxide
  • PLASMA oxygen plasma
  • a PEDOT:PSS (Baytron P4083, available from Bayer AG) film having a thickness of about 40 nm was spin-coated, and the substrate was dried in a vacuum oven at 80 ° C for 8 hours to remove the solvent.
  • the active layer (DPP (TBFu) 2 : PC 61 BM, 3:2, 80 nm) in a chloroform solution was spin-coated on a PEDOT:PSS layer in a nitrogen atmosphere glove box (Vacuum Atmosphere Co.) and dried at 110 ° C. 10 minutes.
  • the ethanol solution of the new cathode buffer material 1 was spin-coated on the active layer and dried at 80 ° C for 10 minutes.
  • a metal Ag (60 nm) cathode was vapor-deposited under a vacuum of 3 x 10 4 Pa.
  • the effective illuminating area of the device is 0.165 cm 2 .
  • Film thickness was measured using a Veeco Dektakl 50 step meter.
  • the deposition rate and thickness of the metal electrode evaporation were measured using a Sycon Instrument thickness/speed meter STM-100. Except that the spin coating process of the PEDOT:PSS film was completed in the atmosphere, all other steps were completed in a glove box in a nitrogen atmosphere.
  • the new cathode buffer material 1 has a solution concentration of 0.5 mg/mL for spin coating and a rotational speed of 2000 r/min.
  • a device coated with ethanol was used as a comparison device.
  • the device structure is as follows:
  • ITO/PEDOT PSS/DPP (TBFu) 2 : PC 6 iBM / Material 1 / Ag
  • ITO/PEDOT PSS/DPP (TBFu) 2 : PC 6 iBM / Ethanol / Ag
  • the organic photovoltaic cell device fabricated by the spin coating method can significantly improve the energy conversion efficiency even after using the metal electrode silver with a high work function, using the cathode buffer layer material.
  • the energy conversion efficiency is 3.02%, which is 1.4 times that of ethanol, indicating that material 1 can effectively assist electron collection of the silver electrode and improve device performance.
  • Table 2 Preliminary characterization results of organic photovoltaic cell devices with new cathode buffer materials 1/Ag, ethanol/Ag

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Abstract

L'invention porte sur un matériau moléculaire de couche tampon de cathode soluble dans des alcools contenant un oxyde de triarylphosphine et un groupe fonctionnel azacyclo et sur un procédé de synthèse et une application de ce dernier. Le matériau de couche tampon de cathode est facilement synthétisé et préparé (par exemple une sublimation sous vide et une purification ne sont pas nécessaires), il a une solubilité souhaitable dans des alcools et un aspect stable en couche mince et il présente une bonne propriété de traitement en solution. L'oxyde de phosphine attracteur d'électrons et le groupe fonctionnel azacyclo sont introduits, ce qui permet d'aider efficacement des électrons en injection/transmission ou collecte à partir de métal tel que l'aluminium (Al), l'argent (Ag), l'or (Au) et l'ITO ou à partir d'une électrode en oxyde métallique, ce qui évite de cette manière l'utilisation d'une électrode métallique à faible travail d'extraction instable dans l'air et ce qui améliore en outre la stabilité du dispositif. De plus, du fait que le matériau de couche tampon de cathode peut interagir avec des ions lithium, des ions potassium, des ions césium et des ions calcium, le matériau de couche tampon de cathode peut en outre être dopé avec un sel inorganique ou un sel organique contenant ces ions, pour former une couche tampon de cathode dopée ou composite, ce qui améliore de cette manière la performance du dispositif.
PCT/CN2013/089024 2013-07-02 2013-12-10 Matériau moléculaire de couche tampon de cathode soluble dans des alcools contenant trois groupes oxyde d'arylphosphine et un groupe fonctionnel azacyclo et procédé de synthèse et son application Ceased WO2015000265A1 (fr)

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CN201310275234.2A CN103374040B (zh) 2013-07-02 2013-07-02 一类含有三芳基磷氧及氮杂环功能基团的醇溶性阴极缓冲层分子型材料及其合成方法与应用

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113880881A (zh) * 2021-10-20 2022-01-04 中化泉州石化有限公司 一种刚性有机膦配体的合成及其在乙烯齐聚中的应用

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103374040B (zh) * 2013-07-02 2016-01-06 华南理工大学 一类含有三芳基磷氧及氮杂环功能基团的醇溶性阴极缓冲层分子型材料及其合成方法与应用
CN103951706B (zh) * 2014-04-30 2016-06-22 华南理工大学 一种基于d-r-a的小分子主体材料及其制备方法、应用
CN104031087A (zh) * 2014-05-27 2014-09-10 华南理工大学 一种醇溶性阴极缓冲层有机分子材料及其制备方法和应用
CN104860991B (zh) * 2015-03-24 2017-10-20 华南理工大学 离子型阴极缓冲层分子型材料及其制备方法和应用
CN105255480B (zh) * 2015-10-08 2017-10-20 华南理工大学 一种含二苯基膦氧的苯并噻二唑发光材料及制备与应用
CN105693773B (zh) * 2016-02-29 2018-05-15 华南理工大学 一种具有高三重态能级的有机分子电子传输材料及其制备方法、应用
WO2017179883A1 (fr) 2016-04-12 2017-10-19 주식회사 엘지화학 Composé et élément électronique organique le comprenant
KR101891168B1 (ko) * 2016-10-31 2018-08-23 엘지디스플레이 주식회사 유기 화합물과 이를 포함하는 유기발광다이오드 및 유기발광 표시장치
CN106905365B (zh) * 2017-02-09 2019-03-12 中国科学院化学研究所 基于三芳基磷氧化合物及其制备方法和应用
CN109721598A (zh) * 2018-12-29 2019-05-07 武汉天马微电子有限公司 化合物、显示面板和显示装置
CN110016053B (zh) * 2019-04-18 2020-08-18 华南理工大学 不对称取代的可溶性吡啶类衍生物及制备、n-掺杂电子传输层与应用
CN112239479B (zh) * 2019-07-17 2021-07-02 华中科技大学 一种有机光电材料、制备方法及其应用与相应器件
CN112958162B (zh) * 2021-02-22 2022-05-24 江南大学 一种用于催化喹唑啉酮合成和烯烃化反应的钯催化剂
CN116813668A (zh) * 2022-03-17 2023-09-29 广东聚华印刷显示技术有限公司 化合物、包含化合物的发光器件以及显示装置

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012173371A2 (fr) * 2011-06-13 2012-12-20 주식회사 엘지화학 Composés originaux et dispositif électronique organique utilisant ces composés
WO2013051875A2 (fr) * 2011-10-05 2013-04-11 주식회사 엘지화학 Dispositif électroluminescent organique et son procédé de fabrication
CN103059064A (zh) * 2012-09-08 2013-04-24 青岛科技大学 手性双膦配体与手性催化剂及制备、应用方法
CN103374040A (zh) * 2013-07-02 2013-10-30 华南理工大学 一类含有三芳基磷氧及氮杂环功能基团的醇溶性阴极缓冲层分子型材料及其合成方法与应用
KR20130135179A (ko) * 2012-05-31 2013-12-10 주식회사 엘지화학 신규한 화합물, 그 제조 방법 및 상기 화합물을 이용한 유기 전자 소자

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5722220B2 (ja) * 2009-08-18 2015-05-20 大電株式会社 有機電界発光素子
DE102009053645A1 (de) * 2009-11-17 2011-05-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtung
CN101747373B (zh) * 2010-01-20 2013-04-10 中国科学院长春应用化学研究所 咔唑类化合物、含有咔唑类化合物的有机电致发光器件及其制备方法
CN101747374A (zh) * 2010-01-21 2010-06-23 中国科学院长春应用化学研究所 含磷氧基团的化合物、含有磷氧基团化合物的有机电致发光器件及其制备方法
CN102827203A (zh) * 2012-09-14 2012-12-19 东莞彩显有机发光科技有限公司 一种磷光主体材料及其制备方法和应用

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012173371A2 (fr) * 2011-06-13 2012-12-20 주식회사 엘지화학 Composés originaux et dispositif électronique organique utilisant ces composés
WO2012173369A2 (fr) * 2011-06-13 2012-12-20 주식회사 엘지화학 Composés originaux et dispositif électronique organique utilisant ces composés
WO2013051875A2 (fr) * 2011-10-05 2013-04-11 주식회사 엘지화학 Dispositif électroluminescent organique et son procédé de fabrication
KR20130135179A (ko) * 2012-05-31 2013-12-10 주식회사 엘지화학 신규한 화합물, 그 제조 방법 및 상기 화합물을 이용한 유기 전자 소자
CN103059064A (zh) * 2012-09-08 2013-04-24 青岛科技大学 手性双膦配体与手性催化剂及制备、应用方法
CN103374040A (zh) * 2013-07-02 2013-10-30 华南理工大学 一类含有三芳基磷氧及氮杂环功能基团的醇溶性阴极缓冲层分子型材料及其合成方法与应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MINO, T. ET AL.: "Palladium-Catalyzed Asymmetric Allylic Alkylation Using Chiral Aminophosphine Ligands", TETRAHEDRON: ASYMMETRY, vol. 12, no. 12, 2001, pages 1677 - 1682 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113880881A (zh) * 2021-10-20 2022-01-04 中化泉州石化有限公司 一种刚性有机膦配体的合成及其在乙烯齐聚中的应用
CN113880881B (zh) * 2021-10-20 2023-11-17 中化泉州石化有限公司 一种刚性有机膦配体的合成及其在乙烯齐聚中的应用

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