WO2023246449A1 - Complexes d'iridium métallique et leur utilisation - Google Patents

Complexes d'iridium métallique et leur utilisation Download PDF

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WO2023246449A1
WO2023246449A1 PCT/CN2023/097309 CN2023097309W WO2023246449A1 WO 2023246449 A1 WO2023246449 A1 WO 2023246449A1 CN 2023097309 W CN2023097309 W CN 2023097309W WO 2023246449 A1 WO2023246449 A1 WO 2023246449A1
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substituted
unsubstituted
compound
group
alkyl
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陈少福
叶康志
戴雷
蔡丽菲
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广东阿格蕾雅光电材料有限公司
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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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Definitions

  • the present invention relates to the technical field of organic electroluminescence, and in particular to an organic luminescent material suitable for organic electroluminescence devices, and in particular to a metal iridium complex and its application in organic electroluminescence devices.
  • OLED organic electroluminescent devices
  • the basic structure of an OLED device is a thin film of organic functional materials with different functions mixed between metal electrodes. It is like a sandwich structure. Driven by current, holes and electrons, holes and electrons are injected from the anode and cathode respectively. After moving a certain distance, it is compounded in the luminescent layer and released in the form of light or heat, thus producing the luminescence of the OLED.
  • organic functional materials are the core components of organic electroluminescent devices. The thermal stability, photochemical stability, electrochemical stability, quantum yield, film formation stability, crystallinity, color saturation, etc. of the material all have an impact. main factor in device performance.
  • organic functional materials include fluorescent materials and phosphorescent materials.
  • Fluorescent materials are usually organic small molecule materials, which generally can only utilize 25% of singlet states to emit light, so the luminous efficiency is relatively low.
  • Phosphorescent materials due to the spin-orbit coupling caused by the heavy atom effect, can not only utilize 25% of the singlet state, but also utilize 75% of the energy of triplet excitons, so the luminous efficiency can be improved.
  • phosphorescent materials started late, and the thermal stability, lifespan, and color saturation of the materials need to be improved. This is a challenging topic.
  • Various compounds have been developed as phosphorescent materials.
  • invention patent document CN107973823 discloses a type of quinoline iridium compound, but the color saturation and device performance of this type of compound, especially luminous efficiency and device life, need to be improved;
  • invention patent document CN106459114 discloses a type of ⁇ -diketone Iridium compounds coordinated by ligands, however, these compounds have a high sublimation temperature and poor color saturation.
  • the device performance, especially the luminous efficiency and device life is not ideal and needs further improvement. and patent documents
  • CN111377969 discloses a type of iridium complex of dibenzofuran biisoquinoline
  • the device performance of these two types of materials cannot meet the display color gamut requirements of BT2020 and needs to be further improved to meet the demand for OLED luminescent materials in the rapidly developing market.
  • the present invention was made to solve the above-mentioned problems, and aims to provide a high-performance organic electroluminescent device and a novel material that can realize such an organic electroluminescent device.
  • the inventors of the present invention have repeatedly conducted in-depth research in order to achieve the above-mentioned object, and as a result, they have found that by using an organometallic iridium complex represented by the following formula (1) and formula (2) as a ligand, high-performance organic iridium complexes can be obtained. Electromechanical luminescent devices.
  • the invention relates to a metal iridium complex and its application.
  • the metal iridium complex has a general formula of Ir(La)(Lb)(Lc), where La is a structure represented by formula (1) and Lb is a structure represented by formula (2).
  • the complex provided by the invention has the advantages of low driving voltage, low sublimation temperature, good optical and electrical stability, high luminous efficiency, long life, high color saturation, etc., and can be used in organic light-emitting devices, especially as red-emitting phosphorescent materials. , has the potential to be used in the AMOLED industry, especially for displays, lighting and automobile taillights.
  • the dotted line indicates the location connected to the metal Ir;
  • Z is O, S, Se
  • R 1 to R 11 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 hetero Aryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl , a substituted or unsubstituted mono-C1-C10 alkyl,
  • R 10 is not hydrogen, deuterium, halogen, or cyano
  • R5 - R7 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and at least one of R5 - R8 is F;
  • the dotted line position indicates the position connected to the metal Ir;
  • Ra-Rg is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 hetero Alkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, or Ra, Rb, and Rc are connected in pairs to form an aliphatic ring, and Re, Rf, and Rg are connected in pairs to form an aliphatic ring;
  • heteroalkyl group, heterocycloalkyl group and heteroaryl group contain at least one O, N or S heteroatom;
  • the substitution is an amino group substituted by deuterium, F, Cl, Br, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 alkyl, nitrile, isonitrile or Substituted by a phosphine group, wherein the substitution ranges from monosubstitution to maximum number substitution;
  • Lc is a monoanionic bidentate ligand
  • Lc and Lb are different and are not OO ligands
  • Lc and La are the same or different, and the difference is that the core structure is different, or the core structure is the same but the substituents are different, or the core structure is the same, the substituents are the same, but the substituent positions are different; or
  • two or three of La, Lb, and Lc are connected to each other to form a multidentate ligand.
  • R 6 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and at least one of R 5 , R 7 and R 8 is F.
  • R 6 is a substituted or unsubstituted C6-C18 aryl group, a substituted or unsubstituted C2-C17 heteroaryl group, and only one of R 5 , R 7 and R 8 is F.
  • the R 10 is a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, and the substitution is by deuterium, F, C1-C5 alkyl or C3-C6 ring Alkyl substitution.
  • R 1 -R 4 and R 11 are independently selected from hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1-C10 alkyl group.
  • At least one of R 8 and R 9 is not hydrogen, deuterium, halogen or cyano.
  • R 8 and R 9 is a substituted or unsubstituted C1-C6 alkyl group or a substituted or unsubstituted C3-C6 cycloalkyl group.
  • the dotted line indicates the location connected to the metal Ir;
  • R 12 to R 19 are independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, amino, amine, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl base, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C18 aryl, substituted or Unsubstituted C2-C17 heteroaryl, substituted or unsubstituted triC1-C10 alkylsilyl, substituted or unsubstituted triC6-C12 arylsilyl, substituted or unsubstituted diC1-C10 alkyl- C6-C30 arylsilyl, substituted or unsubstituted mono-C1-C10
  • At least two of R 16 to R 19 are not hydrogen;
  • At least one group of two adjacent groups in R 12 to R 15 can form an aromatic ring as shown in the following formula (4);
  • the dotted line indicates the position connected to the pyridine ring
  • R 20 to R 23 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C17 hetero Aryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl , a substituted or unsubstituted one-C1-C10 alkyl,
  • heteroalkyl group and heteroaryl group contain at least one O, N or S heteroatom;
  • the substitution is an amino group substituted by deuterium, F, Cl, Br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkyl, nitrile, isonitrile or Phosphine substitution, wherein the substitution ranges from monosubstitution to maximum number substitution.
  • La is one of the following structural formulas, or the corresponding partially or completely deuterated or fluorinated,
  • Lb is one of the following structural formulas, or the corresponding partially or completely deuterated or fluorinated,
  • Lc is one of the following structural formulas, or the corresponding partially or completely deuterated or fluorinated,
  • Another object of the present invention is to provide an electroluminescent device, which includes: a cathode, an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer contains the above-mentioned organic metal iridium complex.
  • the organic layer includes a light-emitting layer, and the metal iridium complex serves as a red light-emitting doping material of the light-emitting layer; or wherein the organic layer includes a hole injection layer, and the metal iridium complex As a hole injection material in the hole injection layer.
  • the material of the present invention not only has the advantages of low driving voltage, low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminous efficiency, long device life, etc., but can be used in organic light-emitting devices, especially as red Luminescent phosphorescent materials have the potential to be used in the AMOLED industry, especially in displays, lighting and automobile taillights.
  • the material of the present invention can convert triplet excited states into light, so it can improve the luminous efficiency of organic electroluminescent devices, thereby reducing energy consumption.
  • Figure 1 is the 1HNMR spectrum of compound La007 of the present invention in deuterated chloroform solution
  • Figure 2 is the 1HNMR spectrum of compound (La007) 2 (Lb005) of the present invention in deuterated chloroform solution,
  • Figure 3 is the ultraviolet absorption spectrum and emission spectrum of the compound (La007) 2 (Lb005) of the present invention in dichloromethane solution.
  • the organometallic iridium compound of the present invention has the general formula Ir(La)(Lb)(Lc), where La is the structure shown in formula (1),
  • the dotted line indicates the location connected to the metal Ir;
  • Z is O, S, Se
  • R 1 to R 11 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 hetero Aryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl , a substituted or unsubstituted mono-C1-C10 alkyl,
  • R 10 is not hydrogen, deuterium, halogen, or cyano
  • R5 - R7 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and at least one of R5 - R8 is F;
  • heteroalkyl group and heteroaryl group contain at least one O, N or S heteroatom;
  • substitution is an amino group, nitrile, isonitrile or phosphine group substituted by deuterium, F, Cl, Br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl, wherein The above substitutions range from single substitution to the maximum number of substitutions;
  • the dotted line position indicates the position connected to the metal Ir;
  • Ra-Rg is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 hetero Alkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, or Ra, Rb, and Rc are connected in pairs to form an aliphatic ring, and Re, Rf, and Rg are connected in pairs to form an aliphatic ring;
  • heteroalkyl group and heterocycloalkyl group contain at least one O, N or S heteroatom;
  • substitution is amino group, cyano group, nitrile substituted by deuterium, F, Cl, Br, C1-C4 alkyl group, C1-C4 alkoxy group, C3-C6 cycloalkyl group, C1-C4 alkyl group, Substituted by isonitrile or phosphine group;
  • Lc is a monoanionic bidentate ligand
  • Lc and Lb are different and are not OO ligands
  • Lc and La are the same or different, and the difference is that the parent core structure is different, or the parent core structure is the same but the substituents are different, or the parent core structure is the same, the substituents are the same, but the substituent positions are different;
  • two or three of La, Lb, and Lc are connected to each other to form a multidentate ligand.
  • carbon number a to b in the expression “substituted or unsubstituted X group having carbon number a to b” represents the carbon number when the X group is unsubstituted.
  • the carbon number of the substituent when the X group is substituted is not included.
  • the C1 to C10 alkyl group is a linear or branched alkyl group, specifically, it is a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, or sec-butyl group. , tert-butyl, n-pentyl and its isomers, n-hexyl and its isomers, n-heptyl and its isomers, n-octyl and its isomers, n-nonyl and its isomers, n- Decyl group and its isomers, etc.
  • Examples of the C3 to C20 cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Alkyl group, etc., preferably cyclopentyl group and cyclohexyl group.
  • Examples of the C2 to C10 alkenyl group include vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hexatrienyl, 2-hexatrienyl, 3 - Hexatrienyl and the like, preferably propenyl and allyl.
  • the C1-C10 heteroalkyl group is a linear or branched alkyl group, cycloalkyl group, etc. containing atoms other than carbon and hydrogen, and examples thereof include mercaptomethylmethyl group, methoxymethyl group, and ethyl group.
  • aryl group examples include phenyl, naphthyl, anthracenyl, phenanthrenyl, tetraphenyl, pyrenyl, chrysyl, benzo[c]phenanthrenyl, benzo[g]chyl, fluorenyl, A benzofluorenyl group, a dibenzofluorenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a fluoranthene group, etc. are preferably a phenyl group and a naphthyl group.
  • heteroaryl group examples include pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuryl, and isophenyl.
  • raw material 1 (18.5g, 71.02mmol, 1.0eq)
  • raw material 2 (10.39g, 85.22mmol, 1.2eq)
  • Pd-132 (251.44mg, 0.35mmol, 0.005eq)
  • potassium carbonate (19.63g, 142mmol, 2.0 eq)
  • toluene 185ml
  • ethanol 56ml
  • deionized water 56ml
  • the film thickness is film, followed by steaming Plating a layer of HTM1 to form a film thickness of left and right films, and then evaporate a layer of HTM2 on the HTM1 film to form a film thickness of thin film, and then use the co-evaporation mode to evaporate the host material 1, the host material 2 and the doping compound on the HTM2 film layer (the ratio is: 48.5%: 48.5%: 3%, the comparison compound X or the compound of the present invention ), the film thickness is ETL is evaporated on the emitting layer using co-evaporation mode: LiQ( The ratio is 50%:50%), and then evaporate Yb on the electron transport layer material Finally, a layer of metal Ag is evaporated as an electrode.
  • the organic electroluminescent device using the compound of the present invention as a dopant has better performance in driving voltage, luminous efficiency and device life than the comparative compound in devices with the same color scale. Superior performance.
  • the metal iridium complex of the present invention has a larger red shift than the comparative compound and can meet the industrial demand for deep red light, especially the BT2020 color gamut.
  • the sublimation temperature is defined as the temperature corresponding to a vacuum degree of 10 -7 Torr and an evaporation rate of 1 angstrom per second.
  • the test results are as follows:
  • the metal iridium complex of the present invention has a lower sublimation temperature, which is beneficial to industrial application.
  • the present invention adds F and aryl/heteroaryl substitutions on isoquinoline through a special combination of substituents. Compared with the existing technology, the present invention unexpectedly provides better device luminous efficiency and improved lifetime. , providing a lower sublimation temperature and a more saturated red luminescence.
  • the above results show that the compound of the present invention has the advantages of low driving voltage, low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminous efficiency, long device life, etc., and can be used in organic electroluminescent devices. Especially as a red-emitting dopant, it has the potential to be used in the OLED industry, especially in displays, lighting and automobile taillights.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)

Abstract

La présente invention concerne des composés d'iridium métallique organique et leur utilisation. Les composés d'iridium métallique organique ont une formule générale Ir(La)(Lb)(Lc), La étant une structure représentée par la formule (1), et Lb étant une structure représentée par la formule (2). Les composés selon la présente invention présentent les avantages d'une faible tension de commande, d'une faible température de sublimation, d'une bonne stabilité optique, d'une bonne stabilité électrique, d'une efficacité lumineuse élevée, d'une longue durée de vie, d'une saturation de couleur élevée, etc, peuvent être utilisés dans des dispositifs électroluminescents organiques, utilisés en particulier en tant que matériau phosphorescent électroluminescent rouge, et ont le potentiel d'être appliqués à l'industrie des AMOLED, en particulier dans l'affichage, l'éclairage et les feux arrières d'automobile.
PCT/CN2023/097309 2022-06-20 2023-05-31 Complexes d'iridium métallique et leur utilisation WO2023246449A1 (fr)

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Citations (7)

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CN111377969A (zh) * 2018-12-27 2020-07-07 广东阿格蕾雅光电材料有限公司 一种有机金属化合物及其应用
CN111620910A (zh) * 2020-06-03 2020-09-04 广东阿格蕾雅光电材料有限公司 一种金属络合物及其应用
CN112830943A (zh) * 2019-11-25 2021-05-25 广东阿格蕾雅光电材料有限公司 一种化合物及其应用
CN113788860A (zh) * 2021-09-28 2021-12-14 四川阿格瑞新材料有限公司 一种金属铱络合物及其应用
CN113831369A (zh) * 2020-06-23 2021-12-24 广东阿格蕾雅光电材料有限公司 一种金属铱络合物及其应用
CN114591371A (zh) * 2020-12-04 2022-06-07 广东阿格蕾雅光电材料有限公司 一种金属络合物及其应用
CN114605474A (zh) * 2020-12-04 2022-06-10 广东阿格蕾雅光电材料有限公司 一种铱络合物及其应用

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111377969A (zh) * 2018-12-27 2020-07-07 广东阿格蕾雅光电材料有限公司 一种有机金属化合物及其应用
CN112830943A (zh) * 2019-11-25 2021-05-25 广东阿格蕾雅光电材料有限公司 一种化合物及其应用
CN111620910A (zh) * 2020-06-03 2020-09-04 广东阿格蕾雅光电材料有限公司 一种金属络合物及其应用
CN113831369A (zh) * 2020-06-23 2021-12-24 广东阿格蕾雅光电材料有限公司 一种金属铱络合物及其应用
CN114591371A (zh) * 2020-12-04 2022-06-07 广东阿格蕾雅光电材料有限公司 一种金属络合物及其应用
CN114605474A (zh) * 2020-12-04 2022-06-10 广东阿格蕾雅光电材料有限公司 一种铱络合物及其应用
CN113788860A (zh) * 2021-09-28 2021-12-14 四川阿格瑞新材料有限公司 一种金属铱络合物及其应用

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