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A star-shaped aromatized inorganic acid radical semiconductor material and its preparation and application

An inorganic acid and free radical technology, which is applied in the manufacture of semiconductor/solid-state devices, semiconductor devices, and the preparation of imino compounds, can solve the problems of difficulty in designing organic small molecule semiconductor materials, high reactivity, etc. Conductivity, the effect of stabilizing free radical signal

Active Publication Date: 2021-10-26
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is difficult to design free radical-containing organic small molecule semiconductor materials due to the high reactivity of free radical molecules.

Method used

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  • A star-shaped aromatized inorganic acid radical semiconductor material and its preparation and application
  • A star-shaped aromatized inorganic acid radical semiconductor material and its preparation and application
  • A star-shaped aromatized inorganic acid radical semiconductor material and its preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Combine 4-boronate-4',4'-dimethoxytriphenylamine (754mg, 1.75mmol) with tris(4-bromophenyl)amine (241mg, 0.5mmol), tetrakistriphenylphosphine palladium (58mg, 0.05mmol), was added to a mixed solvent of 30ml of toluene and 10ml of ethanol, 3ml of 2M sodium carbonate solution was added under nitrogen protection, and reflux reaction was carried out at 110°C for 12h. After separation and purification, 324mg of the reaction intermediate product was obtained, with a yield of 56.2 %. Dissolve 230 mg of the above product in 15 ml of dichloromethane, and add 3 ml of 1M concentration of BBr at -78°C in a nitrogen atmosphere 3 , and then moved to room temperature for 12h, quenched with methanol. The reaction product was further oxidized in air after separation and purification to obtain 184 mg of the product with a yield of 86%.

[0041] The ultraviolet-visible light absorption spectrum and electron paramagnetic resonance spectrum of the product obtained in this embodiment are s...

Embodiment 2

[0050] 4-boronate-4',4'-dimethoxytriphenylamine (754mg, 3.5mmol) and 2,4,6-tris-(4-bromophenyl)-[1,3,5]tri Add oxazine (273mg, 0.5mmol) and tetrakistriphenylphosphine palladium (58mg, 0.05mmol) into a mixed solvent of 30ml of toluene and 10ml of ethanol, add 3ml of 2M sodium carbonate solution under nitrogen protection, and reflux at 110°C After 12 hours of reaction, 373 mg of a reaction intermediate was obtained after separation and purification, with a yield of 62.0%. Dissolve 243 mg of the above product in 15 ml of dichloromethane, and add 3 ml of 1M concentration of BBr at -78°C under a nitrogen atmosphere 3 , and then moved to room temperature to react for 12h, and the reaction product was further oxidized in air after separation and purification to obtain 198mg of the product with a yield of 87.2%.

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Abstract

The invention belongs to the field of organic photoelectric materials, and discloses a star-shaped aromatized inorganic acid free radical semiconductor material as well as its preparation and application. The star-shaped aromatized inorganic acid radical semiconductor material has a general structural formula as shown in the following formula (I). The material obtained in the present invention contains a plurality of phenoxy radicals, can be dissolved in large polar solvents such as dimethyl sulfoxide and alcohol, has good film-forming properties, and can prevent low-polarity solvents such as toluene or chlorobenzene in multilayer devices. Interfacial erosion by solvents. The material has strong thermal stability and electrochemical stability, and the mechanism is that this unique conjugated radical can resonate into a closed-shell structure similar to nitro. In addition, the open-shell radical resonance structure can effectively improve the electrical conductivity, and has good hole transport performance without additional dopants, which can be applied in fields such as organic optoelectronic devices.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a star-shaped aromatized inorganic acid radical semiconductor material and its preparation and application. Background technique [0002] In multilayer organic electronic device structures, in order to overcome the hole charge transport barrier, a hole transport material layer is usually introduced, which functions to transport holes and block electrons, thereby improving the efficiency of the device. [0003] Compared with the commercialized poly(3,4-ethylenedioxythiophene / polystyrene sulfonate (PEDOT:PSS), the organic small molecule hole transport material based on triphenylamine has the characteristics of definite structure, convenient purification and solution processing. , are widely used in the hole transport layer of perovskite solar cells. However, when these hole transport materials are used in organic solar cells, the processing of the active ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/22C07C249/02C07D251/24H01L51/46H01L51/48
CPCC07C251/22C07D251/24H10K71/15H10K85/631H10K85/654H10K85/791
Inventor 李远周佳文曾苗黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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