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Preparation method of phosphine oxide type TADF organic photoelectric material

An organic optoelectronic material, phosphine oxide technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of difficult processing, difficult manufacturing process, low efficiency, etc.

Inactive Publication Date: 2022-04-15
ANYANG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development and application of inorganic LED devices are greatly restricted due to their low efficiency, high processing difficulty, and difficult manufacturing process.

Method used

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  • Preparation method of phosphine oxide type TADF organic photoelectric material
  • Preparation method of phosphine oxide type TADF organic photoelectric material
  • Preparation method of phosphine oxide type TADF organic photoelectric material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of 2,2'-diamino-1,1'-biphenyl:

[0047] Under nitrogen protection, add 40mmol (1.0eq) 2,2'-dinitro-1,1'-biphenyl, 50mL ethanol and 50mL 8M hydrochloric acid mixed solution into a 250mL single-necked flask equipped with a magnet, and wait until the mixture is fully dissolved , add 240mmol tin dichloride (6.0eq) to the reaction system in batches, keep the temperature of the mixture at 100° C. and continue stirring for 6 hours after the addition is complete. After the reaction is complete, the mixed solution is cooled to room temperature, ethanol is distilled off under reduced pressure, NaOH solution is added to the residual solution, and the pH of the solution is adjusted to 8-10, then the mixture is extracted three times with ethyl acetate, the organic phases are combined and sequentially washed with saturated Wash with sodium bicarbonate and saturated brine, dry the organic phase with anhydrous sodium sulfate, filter, and remove the solvent under reduced press...

Embodiment 2

[0049] Synthesis of 2,2'-diacetamido-1,1'-biphenyl:

[0050] Under the protection of nitrogen, put 34.5mmol (1.0eq) 2,2'-diamino-1,1'-biphenyl, 100mL dichloromethane and 90mmol triethylamine into a 250mL flask equipped with a magnet, and after the addition The mixture was cooled in an ice-water bath environment, and then 78 mmol of acetyl chloride was slowly added dropwise to the reaction system with a syringe. After the dropwise addition, the reaction temperature was slowly raised to room temperature and the reaction was stirred overnight. After the reaction was complete, the reaction was quenched with saturated ammonium chloride, the mixture was extracted three times with dichloromethane, the organic phases were combined and washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure to obtain 2,2'- Diacetamido-1,1'-biphenyl 4, yield 93%.

Embodiment 3

[0052] Synthesis of 5,5'-dibromo-2,2'-diacetamido-1,1'-biphenyl:

[0053] Under nitrogen protection, 8.48mmol (1.0eq) of 2,2'-diacetamido-1,1'-biphenyl and 24mL of DMF were added to a 100mL flask equipped with a magnet, and then 18.66 mmol NBS, after the addition was complete, the reaction was stirred overnight at room temperature. After the raw materials are completely reacted, add an appropriate amount of water to the reaction system and a large amount of white solid precipitates out, filter, and wash the filter cake with water and petroleum ether in turn, and the obtained dry filter cake is the target product 5,5'-dibromo-2 ,2'-Diacetamido-1,1'-biphenyl, the yield is 90%.

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Abstract

The invention discloses a preparation method of a symmetric phosphine oxide type TADF organic photoelectric material, and belongs to the field of organic functional materials. 2, 2 '-dinitro-biphenyl is subjected to stannous chloride reduction, amido acylation, electricity-rich aromatic ring bromination reaction and acid deacylation of a protecting group to form free amido, the amido is converted into 5, 5'-dibromo-2, 2 '-diiodo-biphenyl through a diazonium salt process, then the 5, 5'-dibromo-2, 2 '-diiodo-biphenyl is converted into 5, 5'-dibromo-2, 2 '-diiodo-biphenyl, and the 5, 5'-dibromo-2, 2 '-diiodo-biphenyl is converted into 5, 5 The preparation method comprises the following steps: carrying out lithium-iodine exchange on 2, 2 '-diiodo-biphenyl, carrying out nucleophilic substitution reaction on the 2, 2'-diiodo-biphenyl and dichlorophenylphosphine to generate phenylphosphine heterobenzoindole, oxidizing the phenylphosphine heterobenzoindole to form phenylphosphine oxide heterobenzoindole, and carrying out coupling reaction on brominated aromatic hydrocarbon and heteroaromatic hydrocarbon under the catalysis of copper to synthesize the small organic molecule luminescent material with fluorescent reactive oxygen species. The 2, 8-diphenothiazinyl-5-phenyl benzoxphosphine heteroindole synthesized by the method has the potential of becoming an organic micromolecule electroluminescent material and being used as a photosensitizer for organic photoreaction, and fits the development trend of multifunctional application of organic micromolecule materials.

Description

technical field [0001] The invention relates to a preparation method of a symmetrical phosphine oxide type TADF (thermally activated delayed fluorescence) organic photoelectric material, which belongs to the technical field of organic functional materials. Background technique [0002] The light-emitting principle of organic light-emitting diodes is very similar to that of light-emitting diodes, so organic light-emitting diodes are also called OLEDs. In the 1980s, inorganic LED devices were widely used due to their strong structure and low driving voltage. However, the development and application of inorganic LED devices are greatly restricted due to their low efficiency, high processing difficulty, and difficult manufacturing process. Entering the 21st century, the world today has entered the era of informationization, especially the development of various smart phones and other smart devices has attracted more and more people's attention, and these devices have higher and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6568C09K11/06
Inventor 翟圣先董端卫爱民梁艳美冯馨玉陆永欢李权威文惠婷冀豪然
Owner ANYANG INST OF TECH
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