Indolo [3, 2, 1-kl] phenothiazine derivative photoelectric material, application thereof and electronic device

A technology of phenothiazine derivatives and electronic devices, applied in the field of indolo[3, can solve the problems of high cost, increased commercial cost, complicated synthesis and purification steps, etc., and achieves cost reduction, production cost reduction, and high thermal stability. Effect

Pending Publication Date: 2022-07-01
维思普新材料(苏州)有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these commonly used hole-transporting materials usually have relatively complicated synthesis and purification steps and high costs, which increase commercial costs.

Method used

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  • Indolo [3, 2, 1-kl] phenothiazine derivative photoelectric material, application thereof and electronic device
  • Indolo [3, 2, 1-kl] phenothiazine derivative photoelectric material, application thereof and electronic device
  • Indolo [3, 2, 1-kl] phenothiazine derivative photoelectric material, application thereof and electronic device

Examples

Experimental program
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Effect test

preparation example Construction

[0033] The preparation method of the compound of formula M1 is as follows: 2.6g (14.2mmol) phenothiazine, 7.6g (26.1mmol) o-bromoiodobenzene, 0.8g (8.2mmol) sodium tert-butoxide, 0.1g ( 0.3mmol) tri-tert-butyl phosphine tetrafluoroborate, 0.27g (0.3mmol) tris(dibenzylideneacetone)dipalladium, degas the reaction system, add 150mL toluene under nitrogen protection, stir and heat to 106 ℃ to react 12 hours. After the reaction was completed, the system was cooled to room temperature, filtered under reduced pressure, and the filter residue was washed with a large amount of dichloromethane, the filtrate was concentrated to obtain a crude product, and the filter residue was eluted with dichloromethane:petroleum ether=1:4 (volume ratio) The agent was separated and purified on a silica gel column to obtain 4.5 g of M1 with a yield of 89.5%. MS(EI): m / z 352.67[M + ]. Elemental analysis calculated value C 18 H 12 BrNS (%): C 61.03, H 3.41, N 3.95; found: C 61.12, H 3.39, N 3.99.

...

Embodiment 1

[0037] The structural formulas and synthetic routes of compounds 1-9 are as follows:

[0038]

[0039] In a 100mL two-necked flask, 0.5g (1.1mmol) M3, 1.4g (4.0mmol) 4,4'-dimethoxy-4"-boronic acid triphenylamine, 1.7g (16.0mmol) sodium carbonate, 40mL toluene, 6.4 mL of ethanol, 8 mL of water. After the mixture was bubbled with nitrogen for 30 minutes, 0.06 g (0.05 mmol) of tetrakis(triphenylphosphine) palladium catalyst was added, and the mixture was heated and stirred at 106° C. overnight. After the reaction was cooled to room temperature, the mixture Dilute with water (50 mL) and ethyl acetate (50 mL). Extract the aqueous layer with ethyl acetate 100 mL×3. After drying the organic phase with anhydrous sodium sulfate, spin dry to remove the solvent to obtain a crude product. Use petroleum ether: ethyl acetate Ester=4:1 (volume ratio) was used as the eluent solvent for separation and purification on a silica gel column to obtain 1.02 g of a green solid with a yield of 87.9...

Embodiment 2

[0041] The structural formulas and synthetic routes of compounds 1-10 are as follows:

[0042]

[0043] Into a 250mL two-necked flask were successively added 1.3g (2.5mmol) M3, 2.0g (8.9mmol) 4,4'-dimethoxy-diphenylamine, 0.8g (8.2mmol) sodium tert-butoxide, 0.1g (0.3mmol) ) tri-tert-butyl phosphine tetrafluoroborate, 0.27g (0.3mmol) tris(dibenzylideneacetone)dipalladium, degas the reaction system, under nitrogen protection, add 150mL toluene, stir and heat to 106 ℃ and react for 12 hours . After the reaction was completed, the system was cooled to room temperature, filtered under reduced pressure, and the filter residue was washed with a large amount of dichloromethane, and the filtrate was concentrated to obtain a crude product, which was eluted with petroleum ether:ethyl acetate=3:1 (volume ratio) The agent was separated and purified on a silica gel column to obtain 2.1 g of 1-2 with a yield of 86%. MS (MALDI-TOF): m / z 954.3 [M+]. Elemental analysis calculated value C...

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Abstract

The invention provides an indolo [3, 2, 1-kl] phenothiazine derivative, application thereof and an electronic device. According to the indolo [3, 2, 1-kl] phenothiazine derivative disclosed by the invention, a rigid structure of indolo [3, 2, 1-kl] phenothiazine is introduced, so that the indolo [3, 2, 1-kl] phenothiazine derivative is excellent in film-forming property and thermal stability, and can be used for preparing an organic electroluminescent device, a perovskite solar cell, an organic field effect transistor and an organic solar cell. Besides, the indolo [3, 2, 1-kl] phenothiazine derivative can be used as a constituent material of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, a hole blocking layer or an electron transport layer, and can reduce driving voltage, improve efficiency and brightness, prolong the service life and the like. The preparation method of the indolo [3, 2, 1-kl] phenothiazine derivative is simple, raw materials are easy to obtain, and industrial development requirements can be met.

Description

technical field [0001] The invention relates to an indolo[3,2,1-kl]phenothiazine derivative and its application and electronic device, belonging to the technical field of organic optoelectronic materials. Background technique [0002] Since 2009, perovskite solar cells (PeSCs) have attracted much attention and developed rapidly due to their wide and strong absorption band, long exciton diffusion distance, and high photoelectric conversion efficiency. At present, the energy conversion efficiency of perovskite cell devices based on the solution method has exceeded 24% and the stable working time in the atmospheric environment has exceeded 1000 hours. These results fully demonstrate the great potential of perovskite solar cells. [0003] The structure of perovskite cells mainly includes an active layer (perovskite layer), a hole transport layer and an electron transport layer. The hole transport layer functions to extract and transport holes and suppress carrier recombination....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/06H01L51/30H01L51/46H01L51/54
CPCC07D513/06C09K11/06C09K2211/1007C09K2211/1014C09K2211/1037C09K2211/1033C09K2211/1029H10K85/636H10K85/631H10K85/6572H10K85/657
Inventor 朱向东袁晓冬陈华
Owner 维思普新材料(苏州)有限公司
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