Triphenylamine fullerene derivative and preparation method and application thereof

A technology similar to fullerene and triphenylamine, which is applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problems of cumbersome preparation methods of electron transport materials, complex titanium dioxide production process, and difficult product purification and treatment, and achieve reaction The effect of cheap raw materials, strong extraction and transmission capabilities, and easy access to reaction raw materials

Pending Publication Date: 2022-01-28
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As the most typical framework material, titanium dioxide can make perovskite nanocrystals enter the pores of the porous titanium dioxide layer by solution spin coating to form an interconnected absorption layer, which not only plays a supporting role, but also plays a role in transporting electrons. However, the manufacturing process of mesoporous titanium dioxide is complicated and the cost of the device is high; planar heterojunction perovskite solar cells are mainly divided into n-i-p and p-i-n. Titanium dioxide needs to be sintered at a relatively high temperature (>450 °C) under strictly controlled conditions to obtain a conductive phase, which greatly limits the choice of substrate materials, and the preparation process is cumbersome and costly. Oxygen vacancies will be formed under the light, severe hysteresis, device instability and other factors that affect the commercial application of batteries
In the prior art, most of them require high cost to purchase electron transport materials or prepare raw materials. In addition, the preparation methods of related electron transport materials are relatively cumbersome, and the purification of products is difficult, which is not conducive to large-scale application.

Method used

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  • Triphenylamine fullerene derivative and preparation method and application thereof
  • Triphenylamine fullerene derivative and preparation method and application thereof
  • Triphenylamine fullerene derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of trihenylamine fullerene derivatives-C 60 -fused n- (2-cyanoethyl) pyrrolidine-4- (di-p-tolylamino) Phenyl, C 60 And N- (2-cyanoethyl) pyrrolidine-4- (two-pactorino-amino) phenylfalleylene derivative (A1) method and product characterization:

[0044] Proceed as follows:

[0045] 1) Weigh 4-Methyl-N-Phenyl-N- (p-Tolyl) Aniline (5mmol, 1.0eq), using double-drain-tube vacuum filled with nitrogen, reaches the reaction environment of the reaction, add 10.0 to the system ML super dry DMF, place the reaction device in a low temperature cooling circulation device to cool to 0 ° C, then POCL 3 (7.5mmol, 1.5 eq) Added, after the addition is completed, transfer the reaction device into the oil bath, slowly warmed to 75 ° C, reaction 12h, stop the reaction, to be cooled to room temperature, to add excess water to the system to terminate the reaction , Extract three times with EtOAc, no water MGSO 4 Dry, filtration was concentrated, purified with silica gel column chromato...

Embodiment 2

[0051] Preparation of trihenylamine fullerene derivatives-C 60 -fused n- (2-cyanoethyl) Pyrrolidine-4- (Diphenylamino) Phenyl, C 60 The method and product characterization of N- (2-cyanoethyl) pyrrolidine-4- (diphenone) phenylllerene derivative (A2):

[0052] Proceed as follows:

[0053] 1) We will weigh the triphenylamine (5mmol, 1.0 eq), repeated three times with double-drain vacuum, reaches the reaction environment of the reaction, add 10.0 ml of super-oxygen-free DMF to the system, and place the reaction device at low temperature cooling. Cool to 0 ° C in the circulation device, then POCL 3 (7.5mmol, 1.5 eq) Added, after the addition is completed, transfer the reaction device into the oil bath, slowly warmed to 75 ° C, reaction 12h, stop the reaction, to be cooled to room temperature, to add excess water to the system to terminate the reaction , Extract three times with EtOAc, no water MGSO 4 Dry, filtration was concentrated, purified with silica gel column chromatography to o...

Embodiment 3

[0059] Preparation of trihenylamine fullerene derivatives-C 60 -fused n- (2-cyanoethyl) Pyrrolidine-4- (Bis (4-Methoxyphenyl) Amino) Phenyl, C 60 And N- (2-cyanoethyl) pyrrolidine-4- (two-pactoxyenenenenenen) phenylfolhaleylene derivative (A3) method and product characterization:

[0060] Proceed as follows:

[0061] 1) Weigh aniline (1 mmol, 1.0 eq), 8-hydroxyquinoline (0.05 mmol, 0.05 eq), K 3 PO 4 (4 mmol, 4.0 eq), Cucl (0.05mmol, 0.05 eq), 1-IODO-4-Methoxybenzene (2.5mmol, 2.5 eq) in two flasks, construction of the ball gallbladder reflow closing reaction device, using double-distance tube The vacuum nitrogen gas was repeated three times, and 10 ml of super dry DMF reflux was added to the system, and the reaction was filtered, washed with dichloromethane, concentrated to dryness, purified with silica gel column chromatography to obtain a target product 4-Methoxy -N- (4-methoxyphenyl) -n-Phenylaniline;

[0062] 2) Weigh 4-methoxy-N- (4-methodoxyphenyl) -N-Phenylaniline (1 mmol,...

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Abstract

The invention discloses a triphenylamine fullerene derivative and a preparation method and application thereof. The method comprises the following steps: 1) preparing a triphenylamine iodinated product; (2) preparing chlorinated, fluorinated, ethylated and methoxylated products of triphenylamine; (3) preparing hydroformylated triphenylamine and derivatives thereof; and 4) reacting the obtained triphenylamine and derivatives thereof with N-alkylglycine (N-(2-cyanoethyl) glycine, N-methylglycine, N-ethylglycine and N-benzyl glycine) and C60 under anhydrous and anaerobic conditions to obtain the triphenylamine fullerene derivative. The method has the advantages of simple synthesis method, convenient application, strong operability, cheap and easily available reaction raw materials, and high yield. The application of the triphenylamine fullerene derivative prepared by the method as an electron transport material in a perovskite solar cell can realize convenient preparation of the perovskite solar cell, few hysteresis phenomena, and high device efficiency and stability.

Description

technical field [0001] The invention relates to photovoltaic material technology, in particular to a triphenylamine fullerene derivative and its preparation method and application. Background technique [0002] Energy issues have always been widely concerned by researchers. How to effectively develop and utilize clean and green solar energy has become a hot spot of scientific research. Solar cells mainly include inorganic solar cells, dye-sensitized solar cells, organic solar cells and perovskite solar cells. Among them, perovskite solar cells are favored by scientific researchers due to their excellent photoelectric conversion efficiency, which has set off a wave of research on perovskite solar cells. The research boom of mining solar cells. [0003] Perovskite solar cells are composed of conductive glass substrates, electron transport layers, perovskite layers, hole transport layers, and metal electrodes. The working principle of perovskite solar cells is: when the pero...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/96H01L51/46H01L51/42
CPCC07D209/96H10K85/631H10K85/6572H10K30/10Y02E10/549
Inventor 李姝慧邢舟刘福王李亭任雅钟新仙覃竞珍
Owner GUANGXI NORMAL UNIV
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