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Deprotection 9,9'-spirobifluorene dendritic compound and preparation method and application

A compound, spirobifluorene technology, applied in the field of solar cells, can solve the problems of high cost, decomposition and high manufacturing cost of high-purity silicon

Active Publication Date: 2015-08-19
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the first generation of solar technology - crystalline silicon solar cells dominates the photovoltaic field, and its photoelectric conversion efficiency is close to 20%. It is one of the most mature and widely used mature technologies, but the high-purity silicon used in it is expensive , high energy consumption, which seriously restricts the wider industrialization of monocrystalline silicon solar cells (Prog Photovolt-Res Appl, 2009, 17:183–189)
The second-generation thin-film solar cell (GaAs, CdTe, CuInGaSe, etc.) technology has developed rapidly because it can tolerate higher defect density than silicon-based cells, but its large-scale application is also restricted by high manufacturing costs and serious environmental pollution. , unsustainable development of scarce elements and other issues (Renew Sust Energ Rev, 2011, 15:1625-1636)
[0005] At first, perovskite batteries had a fatal problem: perovskite materials were easily decomposed by the liquid electrolyte of the battery, resulting in low battery stability and short life (Chinese Science: Technical Science, 2014, 44:801-821)
At present, the most commonly used hole transport material in perovskite solar cells is still Spiro-OMeTAD (Angew.Chem.Int.Ed.2014, 53, 4085-4088), but its solubility is poor and purification is difficult, so the price High, more than 5 times the price of gold, it is necessary to find more effective, stable and cheap new hole transport materials to improve the conversion efficiency of perovskite solar cells

Method used

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  • Deprotection 9,9'-spirobifluorene dendritic compound and preparation method and application
  • Deprotection 9,9'-spirobifluorene dendritic compound and preparation method and application
  • Deprotection 9,9'-spirobifluorene dendritic compound and preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The preparation of embodiment one compound 1

[0054] The reaction scheme is as follows:

[0055]

[0056] This can be achieved through the following three options:

[0057] Scheme 1: Add 20g (0.062mol) 4,4'-dibromodiphenylamine and 20.3g (0.093mol) (BOC) to a three-necked flask with a volume of 250mL 2 O, mix well to obtain mixture I, add 80g THF (tetrahydrofuran) to the above mixture I, nitrogen protection, mechanical stirring, the system is completely dissolved, and the system is brown and clear at this time. Slowly add 1.5g (0.012mol) of DMAP (4-dimethylaminopyridine) to the system, a large number of bubbles are generated, and the system turns brownish yellow and clear. At this time, the temperature of the oil bath is raised to 70°C, and the system is refluxed for 2 hours. After the reaction was completed, the temperature was lowered to room temperature, and the solvent was removed under reduced pressure to obtain 33 g of brown oil. Filter through a silica gel...

Embodiment 2

[0060] The preparation of embodiment two compound 2

[0061] The reaction scheme is as follows:

[0062]

[0063] This can be achieved through the following three options:

[0064] Scheme 1: Add 23.7g (0.10mol) 4,4'-dimethoxydiphenylamine, 20g (0.047mol) compound 1 (prepared by Scheme 1 of Example 1), 0.86g ( 9.4×10 -4 mol)Pd 2 (dba) 3 , 0.54g (1.88×10 -3 mol)(t-Bu) 3 P·BF 4 and 15.8g (0.141mol) of potassium tert-butoxide, mix uniformly to obtain mixture II, add 400g toluene to mixture II, pass nitrogen protection, start mechanical stirring, stir evenly, the system becomes black and turbid, heat up to 115°C, reflux Reaction 4h. After the reaction was complete, the system was cooled to room temperature, quenched by pouring into 200g of water, separated, the aqueous phase was extracted with (50mL×2) ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure to obtain 36.4 g of dar...

Embodiment 3

[0067] The preparation of embodiment three compound 3

[0068] The reaction scheme is as follows:

[0069]

[0070] This can be achieved through the following three options:

[0071] Scheme 1: Add 4.1g (5.67×10 -3 mol) Compound 2 (prepared by Scheme 1 of Example 2), 20 g of dichloromethane, and start stirring. After complete dissolution, 41 g of TFA (trifluoroacetic acid) was added to the system, and reacted at room temperature for 10 min. After the reaction was complete, the solvent was removed under reduced pressure to obtain 5.1 g of a black solid. Add 50g ethyl acetate and 50g mass fraction of 10% NaOH aqueous solution to the system, stir for 0.5h, separate the liquids, extract the aqueous phase with 20mL ethyl acetate, combine the organic phases, add 20g anhydrous sodium sulfate to dry, desolventize, and oxidize Aluminum was filtered, and dichloromethane was rinsed to obtain 3.1 g of compound 3. Yield 87.8%. 1 H NMR (400MHz, acetone-d6) δ / ppm: 7.38 (d, J = 9.0Hz,...

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Abstract

The invention relates to a dendritic compound using 9,9'-spirobifluorene as a kernel and methoxyl group substituted diarylamine as a branch compound, and the application of the dendritic compound in perovskite solar batteries, and belongs to the field of the preparation of solar battery materials. The preparation method comprises the following steps: firstly, reacting 4,4'-dibrom diphenylamine which is protected through tert-butyloxycarbonyl with 4,4'-dimethoxy diphenylamine or 4,4'-N,N'-(4,4'-dimethoxy diphenyl) diphenylamine so as to generate a branch with a protecting group, and then carrying out deprotection under the action of trifluoroacetic acid so as to generate a first-generation branch and a second-generation branch respectively; reacting the first-generation branch or the second-generation branch respectively with the bromo-9,9'-spirobifluorene compound under the action of a palladium catalyst so as to obtain a first-generation 9,9'-spirobifluorene spirofluorene dendritic compound or a second-generation 9,9'-spirobifluorene spirofluorene dendritic compound. The dendritic compound disclosed by the invention has better heat stability and solubility, is used as a hole transport material for the perovskite solar batteries, and has higher photoelectric conversion efficiency.

Description

technical field [0001] The invention belongs to the field of solar cells, and in particular relates to a 9,9'-spirobifluorene dendritic compound and a preparation method and application thereof. Background technique [0002] Solar energy is an inexhaustible and inexhaustible source of energy in the world. The energy produced by light for one year is 1.5×10 18 kWh, while the known energy sources of oil, coal and natural gas are 17.5×10 15 kWh, 1.4×10 15 kWh and 5.5×10 15 kWh. It can be seen that the energy produced by light for one year is more than a hundred times the energy provided by the total amount of known fossil energy reserves in the world. Today, with the global depletion of fossil energy and increasing environmental pollution, solar energy has become one of the ideal supplementary and alternative energy sources for non-renewable energy such as oil, coal, and natural gas (The Physics of Solar Cells, Imperial College Press, 2003). Solar cells are the most effic...

Claims

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Application Information

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IPC IPC(8): C07C217/92C07C213/08H01L51/46
CPCY02E10/549Y02P20/55
Inventor 任辉彩史汝金庞茂印胡葆华孟凡民葛立权安隆隆
Owner VALIANT CO LTD
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