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Self-compensating free radical ion salt, preparation method thereof, and photoelectric device

A technology of photoelectric devices and free radicals, which is applied in the direction of electric solid devices, sulfonate preparation, photovoltaic power generation, etc., can solve the problems of poor interface modification ability, low stability, limited free radical concentration, etc., and achieve the overall efficiency of the device , increase the concentration, and promote the effect of charge transfer

Active Publication Date: 2020-02-28
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a self-compensating free radical ion salt and its preparation method, and a photoelectric device, aiming at solving the problem that the free radical concentration of the existing self-doped cathode interface layer material is limited and Low stability, which leads to poor interface modification ability

Method used

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  • Self-compensating free radical ion salt, preparation method thereof, and photoelectric device
  • Self-compensating free radical ion salt, preparation method thereof, and photoelectric device
  • Self-compensating free radical ion salt, preparation method thereof, and photoelectric device

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preparation example Construction

[0038] see figure 1 , figure 1 A flow chart of a preferred embodiment of a self-compensating free radical ion salt preparation method provided by the present invention, as shown in the figure, includes the following steps:

[0039] S10, mixing an N-containing conjugated heterocyclic ring with a halogenated hydrocarbon, and reacting to obtain a free radical ion salt precursor;

[0040] S20 / Adding a counter ion salt to the precursor of the free radical ion salt and mixing, reacting to obtain the self-compensating free radical ion salt.

[0041] Through the method provided in this example, the self-compensating free radical ion salt can be prepared simply and quickly. The prepared self-compensating free radical ion salt contains free radicals with high concentration and high stability. The principle of achieving the above effects is as follows:

[0042] In this example, by mixing N-heteroconjugated heterocyclic rings with quaternary ammonium halogenated hydrocarbons, while rea...

Embodiment 1

[0071] The preparation of embodiment 1TPyPy-TFSI radical ion salt

[0072] The specific synthetic route is as figure 2 shown. First weigh 510mg of TPyPy (1mmol) into a 25mL Chirank tube, add 5mL of ultra-dry DMF and 1.2g of methyl iodide (8mmol, excess) in sequence, then freeze the system into a solid with liquid nitrogen, vacuumize the system with an oil pump, and then fill it with Inject dry argon, and repeat the pumping three times. The system was sealed, then placed in a reactor at 150°C, and stirred in the dark for 12 hours, then cooled to room temperature and then transferred to a glove box. The suspension was added dropwise to the dry diethyl ether solution, stirred to disperse, precipitated, and then filtered to obtain a brown-yellow solid powder. Wash the solid phase successively with petroleum ether and tetrahydrofuran, and drain it for later use. Then disperse the brown yellow solid powder in an appropriate amount of ultra-dry methanol solution, add excess lith...

example 2

[0075] Example 2: Preparation of BCP-SBS radical ion salt

[0076] The specific synthetic route is as image 3 shown. First, weigh 720mg of BCP (2mm) into a 25mL ultra-dry Chirank tube, then add 10mL of re-distilled 1,2-dibromoethane, use liquid nitrogen to reduce the suspension to below the freezing point, and use an oil pump to Vacuumize, refill with dry argon, repeat this operation three times, then seal the system away from light and place it in a reactor at 140°C, stir at this temperature for 12 hours, cool to room temperature, and transfer to a glove box for processing. Add the brown suspension dropwise to the stirred ultra-dry diethyl ether solution, then filter to obtain a tan solid powder, wash with petroleum ether and tetrahydrofuran ultra-dry solution successively, drain and transfer to the outside of the glove box for later use. Dissolve the solid in an appropriate amount of methanol solution, add excess sodium saccharin, stir at room temperature for 3 to 5 hours...

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Abstract

The invention provides a self-compensating free radical ion salt, a preparation method thereof and sphotoelectric device. The preparation method comprises the following steps: mixing an N-containing conjugated heterocycle with a halogenated hydrocarbon, and reacting to obtain a free radical ion salt precursor; and adding a counter ion salt into the free radical ion salt precursor, mixing, and reacting to obtain the self-compensating free radical ion salt. The method comprises the following steps: carrying out quaternary ammonium reaction on the N-heteroconjugated heterocycle and the halogenated hydrocarbon to generate a quaternary ammonium salt, inducing to generate free radicals by adopting thermal excitation method, and carrying out internal anion exchange on anions of the counter ion salt and the free radicals to improve the concentration and stability of the free radicals in an obtained system. The self-compensating free radical ion salt obtained by the preparation method can be used for modifying a cathode in a photoelectric device, the interface contact resistance is reduced, and the comprehensive efficiency and the device stability of the organic photoelectric device are improved.

Description

technical field [0001] The invention relates to the field of cathode modification layer materials of organic photoelectric devices, in particular to a self-compensating radical ion salt, a preparation method thereof, and a photoelectric device. Background technique [0002] In conventional photoelectric devices, a large electron injection / extraction barrier is formed between the cathode made of metal and the organic functional layer (electron transport layer, organic light-emitting layer or solar active layer) in contact with it, which affects the The injection and extraction of charge carriers between the electrode and the organic functional layer reduces the overall efficiency of the organic photoelectric functional conversion device. [0003] In order to reduce the interfacial contact barrier to achieve "quasi-ohmic" contact, a suitable cathode interfacial layer is usually inserted between the cathode metal and the organic functional layer, and a single interface inductio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/16C07D403/14C07D498/16C07D513/22C07D487/22C07D291/08C07C303/40C07C311/48C07D275/06C07C303/32C07C309/06H01L51/44
CPCC07D471/16C07D403/14C07D498/16C07D513/22C07D487/22C07D291/08C07C303/40C07D275/06C07C303/32H10K30/80C07C311/48C07C309/06Y02E10/549
Inventor 杨楚罗尹校君刘小辉
Owner SHENZHEN UNIV
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