Bismuth-containing compound, preparation method and application

A technology of bismuth compounds and polymer compounds, which is applied in the fields of bismuth organic compounds, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of few types of light extraction layers and unfavorable processing.

Pending Publication Date: 2022-04-22
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many types of light extraction layers commonly used at present, and most of them are some metal oxides. They all need to be formed into films by evaporation, which is not conducive to large-area processing.

Method used

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  • Bismuth-containing compound, preparation method and application
  • Bismuth-containing compound, preparation method and application
  • Bismuth-containing compound, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1 (synthesis of symmetrically substituted compounds):

[0045]

[0046] Under an inert gas protective atmosphere, dissolve 1.57g bromobenzene into 60ml anhydrous THF, add two grains of iodine, 2.16g fresh magnesium chips, heat to initiate the reaction, and slowly add 7.85g bromobenzene, heat to reflux for 2h, cool, Take 6.3g BiCl 3 Dissolved in 20mlTHF and added to Grignard reagent, stirred overnight. The reaction was quenched by adding water, extracted, concentrated and purified by column chromatography to obtain 5.2 g of white solid with a yield of 59%. The refractive index is 1.82.

[0047] For the synthesis of asymmetric bismuth compounds, the ratio of Grignard reagents can be changed to synthesize the product.

Embodiment 2

[0048] Embodiment 2 (synthesis of asymmetrically substituted compounds):

[0049]

[0050] Under an inert gas atmosphere, dissolve 1.57g of bromobenzene into 60ml of anhydrous THF, add two grains of iodine and 2.16g of fresh magnesium chips, heat to initiate the reaction, and slowly add 7.85g of bromobenzene, heat to reflux for 2h, cool, Take 9.45g BiCl 3 Dissolved in 20mlTHF and added to Grignard reagent, stirred overnight. The reaction was quenched by adding water, extracted, concentrated and purified by column chromatography to obtain 7.2 g of white solid with a yield of 60.3%.

[0051] Under an inert gas protective atmosphere, dissolve 0.5g of bromonaphthalene in 30ml of anhydrous THF, add two grains of iodine, 0.36g of fresh magnesium chips, heat to initiate the reaction, and slowly add 1.56g of bromobenzene, heat to reflux for 2h, cool, Take 3.98g of diphenylbismuth chloride dissolved in 10ml of THF and add to the Grignard reagent, and stir the reaction overnight. ...

Embodiment 3

[0052] Embodiment 3 (synthesis of condensed ring compounds):

[0053]

[0054] Under anhydrous and oxygen-free nitrogen atmosphere, take 1.38g of reaction materials and dissolve in 100ml of tetrahydrofuran, cool down to -78°C, add n-BuLi 24ml (2.5M) dropwise to it, after the dropwise addition, the reaction system is heated and refluxed for 3h , the temperature was lowered to -78°C again, and 1.335 g of bismuth tribromide was added. Raise to room temperature, stir for 1 h, cool down to 0°C, add 10.3 g of diisopropylethylamine, and heat to reflux overnight. Cooled, quenched with water, extracted with chloroform, concentrated, and purified by column chromatography to obtain 0.52 g of a yellow solid with a yield of 30.1%. The refractive index is 1.91.

[0055] The bismuth-containing compound we prepared was used to prepare top-emitting devices, and the device structure is as follows figure 1 As shown, the device performance is shown in the table below:

[0056] ligh...

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Abstract

The invention relates to the field of organic light-emitting materials, in particular to a bismuth-containing compound, a preparation method and application. According to the bismuth-containing compound, different organic functional groups are introduced to bismuth to change electron distribution and molecular accumulation of the material and regulate and control the refractive index and thermal stability of the material, and the introduction of the different functional groups can change the solubility of the material, so that an organic light extraction layer material capable of being processed by a solution is realized. Meanwhile, the bismuth-based organic compound has strong fluorescence, can be used as a light extraction layer and can also be used as a light emitting layer of an OLED device, and various functional applications of one material are realized.

Description

technical field [0001] The invention relates to the field of organic luminescent materials, in particular to a bismuth-containing compound, a preparation method and an application. Background technique [0002] Due to the advantages of small thickness, light weight, no viewing angle, simple manufacturing process, low cost, high luminous efficiency, and roll-to-roll processing, organic electroluminescent diodes (OLEDs) have a wide range of applications in the field of new light emitting and display. Applications, which have been successfully applied in the fields of smart phones, TVs, lighting, and large-screen displays, have received extensive attention and research from academia and industry. [0003] Since the discovery of organic light-emitting diodes (OLEDs), organic small molecule light-emitting materials and light-emitting devices have continued to make progress, and both luminous efficiency and stability have been greatly improved. According to the OLED device struct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/94C08G61/12C09K11/06H01L51/54H01L51/52
CPCC07F9/94C08G61/12C09K11/06C08G2261/11C08G2261/334C08G2261/143C09K2211/1014C09K2211/1007C09K2211/1029C09K2211/1059C09K2211/1088C09K2211/1011C09K2211/1092C09K2211/1037C09K2211/1033C09K2211/104C09K2211/1096C09K2211/1044H10K85/636H10K85/626H10K85/633H10K85/654H10K85/6574H10K85/657H10K85/6572H10K50/85
Inventor 孟鸿陈小龙缪景生贺耀武施明蒋明杰刘铭贺超
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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