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Iridium complex taking thiobis diaryl/aromatic heterophosphamide compound as auxiliary ligand

A technology of iridium complexes and ligands, applied to compounds containing elements of group 8/9/10/18 of the periodic table, indium organic compounds, platinum group organic compounds, etc., can solve carrier imbalance and reduce device Efficiency and other issues, to achieve the effect of simple preparation method, improved electron mobility, and easy synthesis

Active Publication Date: 2018-09-04
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

AI Technical Summary

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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  • Iridium complex taking thiobis diaryl/aromatic heterophosphamide compound as auxiliary ligand
  • Iridium complex taking thiobis diaryl/aromatic heterophosphamide compound as auxiliary ligand
  • Iridium complex taking thiobis diaryl/aromatic heterophosphamide compound as auxiliary ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Preparation of Auxiliary Ligand Thiobisaryl / Aryl Heterophosphorimide

[0034] React bromobenzene and magnesium powder to obtain Grignard reagent, then react with phosphorus trichloride, diphenyl diphenylphosphorus chloride derivatives are distilled off under reduced pressure, and further react with hexamethylsilyl amine, and separate by column chromatography, Then oxidize with sulfur powder in tetrahydrofuran under anaerobic conditions to obtain thiobisdiphenylphosphorimide

[0035] Other thiobis-diaryl / aryl-heterophosphorimides can be prepared by the above method:

[0036]

Embodiment 2

[0037] The preparation of embodiment 2 iridium complexes of the present invention

[0038] The main ligand 2-phenylpyridine and IrCl 3 Reflux in the ethoxyethanol solution in the ratio of 2:1 for 10 hours, cool and filter to obtain the chlorine bridge complex of iridium; The potassium hydroxide of base phosphoramidite auxiliary ligand and 20mmol (1.12 grams) was refluxed in ethoxyethanol for two hours to obtain the crude product of iridium complex, and column chromatography obtains 17.28 grams of pure products Stpip 1 (productivity: 91%)

[0039] Further place 5 g of Stpip 1 in the quartz tube at 10 -5 Heating and sublimation purification under Pa vacuum conditions obtained 4.5 grams of luminescent material (sublimation rate 90%) that met the requirements for device preparation. The response looks like this:

[0040]

[0041] Gained iridium complex Stpip 1 is analyzed as follows by proton nuclear magnetic resonance spectrum and high resolution mass spectrometry:

[004...

Embodiment 3

[0048] Embodiment 3 Preparation of iridium complex Stpip 1 organic electroluminescent device

[0049] Taking Stpip 1 as the light-emitting center of the light-emitting layer to prepare an organic electroluminescent device as an example, the preparation of the organic electroluminescent device of the present invention will be described. 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....

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Abstract

The invention relates to a novel iridium complex taking heterocyclic nitrogen as a main ligand and taking a thiobis diaryl / aromatic heterophosphamide compound as an auxiliary ligand. The heterocyclicnitrogen and phosphorus-sulfur groups in iridium complex molecules are helpful for increasing the electron mobility of a material and regulating the luminescence color, injection and transmission of cavity and electrons can be balanced, a composite area of a carrier is widened, the equipment efficiency is increased, and the efficiency roll-off is reduced. The iridium complex has the advantages ofsimple synthesis, stable chemical properties, easy sublimation purification, and excellent equipment performance, and provides convenience for acquiring a high-efficiency organic electroluminescent device and an application of the high-efficiency organic electroluminescent device in the fields of illumination and display.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent devices, in particular to a class of iridium complex light-emitting materials with thiobisdiaryl / aryl heteroyl phosphorimides as auxiliary ligands and electroluminescent devices using the materials. 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 electroluminescent materials an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185C09K2211/1029C09K2211/1014C09K2211/1044C09K2211/1048H10K85/342
Inventor 郑佑轩王毅潘毅左景林夏景成朱成成张锋
Owner 马鞍山南京大学高新技术研究院
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