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A kind of binaphthyl organic polymer hole transport material and its synthesis method and application

A technology of hole transport material and synthesis method, which is applied in the field of binaphthyl organic polymer hole transport materials and its synthesis, and can solve the problems of unfavorable perovskite battery device stability, reduced material hole mobility, and molecular stacking. Low density and other issues, to achieve the effect of being conducive to commercial production and application, improving hole mobility, and simple preparation process

Active Publication Date: 2021-04-13
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, more long chains can easily lead to low packing density of molecules, resulting in a decrease in the hole mobility of the material; sulfonic acid groups make the molecules weakly acidic, which will destroy the perovskite material, which is not conducive to improving the device stability of the perovskite battery

Method used

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  • A kind of binaphthyl organic polymer hole transport material and its synthesis method and application
  • A kind of binaphthyl organic polymer hole transport material and its synthesis method and application
  • A kind of binaphthyl organic polymer hole transport material and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of 6,6'-bis(4-(bis(4-(4-methoxyphenyl)amino)phenyl)-2,2'-binaphthol

[0040]

[0041] 6,6'-dibromo-2,2'-binaphthol 15 (8.71g, 19.61mmol), 4-boronic acid pinacol ester-4',4'-dimethoxytriphenylamine 16 (19.5 g, 45.21mmol) was dissolved in tetrahydrofuran, an aqueous solution of sodium carbonate (6.24g, 58.87mmol, 30ml) was added for nitrogen replacement under stirring, tetrakis(triphenylphosphine)palladium (680mg, 0.588mmol) was added, and the temperature was slowly raised to reflux; The reaction was about 8 hours, and the reaction was monitored by TLC. After the reaction, add water to quench the reaction, extract, and recrystallize the obtained crude product with petroleum ether and ethyl acetate to obtain 11.5 g of the final product, with a yield of 65.7%

[0042] 1 H NMR (400MHz, DMSO) δ9.28(s, 2H), 8.06(s, 2H), 7.90(d, J=8.9Hz, 2H), 7.56(d, J=8.5Hz, 4H), 7.45(t ,J=15.2Hz,2H),7.33(d,J=8.9Hz,2H),7.16–6.95(m,11H),6.89(m,12H),5.77(s,1H),3.74(s,12H) .

...

Embodiment 2

[0045] Preparation of Polymer PI-1

[0046]

[0047] 6,6'-bis(4-(bis(4-(4-methoxyphenyl)amino)phenyl)-2,2'-binaphthol Z5 (400mg, 0.45mmol), 1,2 -Dibromoethane (85mg, 0.45mmol) and sodium carbonate (192mg, 1.81mmol) were added to 5ml of dry N,N-dimethylformamide, stirred at 100°C for 24h, TLC monitored the completion of the reaction of the raw materials, and cooled the reaction system to room temperature , filtered, the filtrate was dropped in absolute ethanol under stirring, stirred, suction filtered, and the filter cake was dried under reduced pressure to obtain 250 mg of a yellow product with a yield of 59%.

Embodiment 3

[0049] Preparation of polymer PI-3

[0050]

[0051] 6,6'-bis(4-(bis(4-(4-methoxyphenyl)amino)phenyl)-2,2'-binaphthol Z5 (400mg, 0.45mmol), 1,6 - Add dibromohexane (111mg, 0.45mmol) and sodium carbonate (192mg, 1.81mmol) into 5ml of dry N,N-dimethylformamide, screw the bottle tightly, and stir at 100°C for 24h, TLC monitors the completion of the reaction of raw materials , the reaction system was cooled to room temperature, filtered, the filtrate was dropped into absolute ethanol under stirring, stirred, suction filtered, the filter cake was taken and dried under reduced pressure to obtain 220 mg of off-white solid powder with a yield of 50%.

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Abstract

The invention relates to a binaphthyl organic polymer hole transport material and its synthesis method and application. This type of compound uses the triarylamine group with adjustable energy level as the electron-donating unit, and the binaphthyl group with a certain helical structure as the polymer skeleton. By using different side chains in series to form a high polymer, it has the formula (PI ) shows the structure. The polymerization reaction of the compound adopts non-palladium-catalyzed polymerization reaction, the conditions are mild, the yield is high, and the cost is low. This type of compound has a non-conjugated polymer main chain structure, has good flexibility, solubility and film-forming property, and can be used to prepare a hole transport layer in a perovskite solar cell. The perovskite precursor liquid has good wettability on the surface of the hole transport layer, and high-quality perovskite crystals can be prepared to achieve high-efficiency photoelectric conversion and prolong battery life.

Description

technical field [0001] The invention relates to a binaphthyl organic polymer hole transport material and its synthesis method and application. Background technique [0002] Solar cells can effectively utilize clean and renewable solar energy to achieve high-efficiency photoelectric conversion, which is expected to solve the increasingly severe energy crisis and environmental pollution problems. Perovskite solar cells are a new type of solar cells based on organic-inorganic hybrid perovskite materials. In 2009, the efficiency of perovskite solar cells was only 3.8% when they first came out (JACS, 2009, 131(17): 6050), but today, 10 years later, the laboratory efficiency of perovskite solar cells has jumped to 25.2%. However, due to the poor stability of perovskite solar cell devices, its commercial application is restricted. Therefore, optimizing the key materials of perovskite batteries to ensure high-efficiency photoelectric conversion of the device and prolonging the se...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/40H01L51/46
CPCC08G65/4006C08G65/4087C08G2650/50C08G2650/24H10K85/111H10K85/151Y02E10/549
Inventor 张文华宗雪平梁茂薛松朱连杰
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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