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A Class of Bisthioaromatic/Aromatic Heterocyclic Phosphate Compounds as Iridium Complexes as Auxiliary Ligands

An iridium complex, electromechanical technology, applied in the direction of indium organic compounds, platinum group organic compounds, compounds containing elements of group 8/9/10/18 of the periodic table, etc., can solve the problem of reducing device efficiency and carrier imbalance. and other problems, to achieve the effect of improving electron mobility, simple preparation method, easy sublimation and purification

Active Publication Date: 2020-12-11
马鞍山南京大学高新技术研究院 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] As we all know, the hole mobility of the hole layer is much greater than the electron mobility of the electron layer, which will lead to the imbalance of carriers and reduce the device efficiency.

Method used

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  • A Class of Bisthioaromatic/Aromatic Heterocyclic Phosphate Compounds as Iridium Complexes as Auxiliary Ligands
  • A Class of Bisthioaromatic/Aromatic Heterocyclic Phosphate Compounds as Iridium Complexes as Auxiliary Ligands
  • A Class of Bisthioaromatic/Aromatic Heterocyclic Phosphate Compounds as Iridium Complexes as Auxiliary Ligands

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Experimental program
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Effect test

Embodiment 1

[0033] Embodiment 1 Preparation of auxiliary ligand bisthiodiphenyl phosphate sodium aqueous solution

[0034] Reflux bromobenzene and phosphorus trichloride (2:1) in toluene under anaerobic conditions for two hours, separate by column chromatography after cooling to obtain diphenylphosphorus chloride, and then dissolve them with sulfur powder in toluene and anaerobic conditions. Reflux for two hours under conditions, then stir in sodium hydrogensulfide aqueous solution for two hours to obtain dithiodiphenylsodium phosphate aqueous solution The yield reached 100%.

[0035] The above method can be used to prepare other bisthio aromatic ring / heteroaryl ring phosphoric acid compound sodium salt aqueous solution:

Embodiment 2

[0036] The preparation of embodiment 2 iridium complexes of the present invention

[0037] The main ligand 2-phenylpyridine and IrCl 3 Reflux 10 hours in ethoxyethanol solution with the ratio of 2:1, the chlorine bridge complex of iridium obtained by cooling filtration; Refluxed in ethoxyethanol for two hours to obtain the crude product of the iridium complex, and column chromatography yielded 13.80 g of pure SSdpp 1 (yield: 92%). and further placed 5 g of SSdpp 1 in a quartz tube at 10 -5 Heating and sublimation purification under Pa vacuum conditions obtained 4.7 g of luminescent materials (sublimation rate 94%) that met the requirements for device preparation. The response looks like this:

[0038]

[0039] Gained iridium complex SSdpp 1 is analyzed as follows by proton nuclear magnetic resonance spectrum and high-resolution mass spectrometry:

[0040] 1 H NMR (400MHz, CDCl 3 )δ8.56(d,2H),8.16(t,J=7.4Hz,2H),7.82(d,J=4.3Hz,2H),7.52-7.45(m,10H),7.42–7.15(m,14H ), 6....

Embodiment 3

[0046] Preparation of Example 3 Iridium Complex SSdpp 1 Organic Electroluminescent Device

[0047] The preparation of the organic electroluminescent device of the present invention will be described below by taking SSdpp 1 as the luminescent center of the luminescent layer to prepare an organic electroluminescent device as an example. The structure of OLEDs device includes: substrate, anode, hole injection material, hole transport layer, organic light-emitting layer, electron transport layer, electron injection material and cathode. The substrate is glass, the anode is indium tin oxide, and the hole injection layer is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzene Phenanthrene HAT-CN (5nm), the evaporation rate is 0.05nm / s; the hole layer is made of 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline TAPC material (50nm) , the evaporation rate is 0.05nm / s; the electron transport layer adopts 1,3,5-tris[(3-pyridyl)-3-phenyl]benzene TmPyPb (50nm), the evaporation rate is 0.0...

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Abstract

The invention relates to a novel iridium complex with a nitrogen heterocyclic ring as the main ligand and a dithioaromatic / aromatic heterocyclic phosphoric acid compound as an auxiliary ligand. The nitrogen heterocycle and phosphorus-sulfur group in the iridium complex molecule help to improve the electron mobility of the material and regulate the luminous color, thereby balancing the injection and transport of holes and electrons, broadening the recombination area of ​​carriers, and improving device efficiency. , reducing efficiency roll-off. The iridium complex of the invention has the advantages of simple synthesis, stable chemical properties, easy sublimation and purification, and excellent device performance, which provides convenience for obtaining high-efficiency organic electroluminescent devices and their applications in the fields of lighting and display.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent devices, in particular to a kind of iridium complex luminescent material with dithioaromatic / aromatic heterocyclic phosphoric acid compounds as auxiliary ligands and an electroluminescent device using the material. Background technique [0002] Against the background of increasing global energy demand and worrying ecological environment, governments of various countries have vigorously developed sustainable energy-saving technologies and industries based on high technology. Organic Light-emitting Diode (OLED for short), also known as organic light-emitting diode, is a device in which voltage is applied to convert electrical energy into light energy. Since 1987, Dr. Qingyun Deng of Kodak Company of the United States published OLED with low-voltage start-up, high-efficiency and high-brightness small-molecule organic thin-film double-layer structure, the research on electroluminesc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/1029C09K2211/1014C09K2211/1044C09K2211/185C09K2211/1088C09K2211/1092C09K2211/1074H10K85/342
Inventor 郑佑轩王毅潘毅左景林苏宁
Owner 马鞍山南京大学高新技术研究院
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