Derivative of dibenzofuran and preparation method and application thereof

A technology of dibenzofuran and derivatives, which is applied in the field of dibenzofuran derivatives and its preparation and application, and can solve the problem of low glass transition temperature of organic small molecule compounds, uncertain molecular weight of polymer materials, and difficulty in industrialization Production and other issues, to achieve the effect of favorable battery properties, high photoelectric conversion efficiency, and low price

Active Publication Date: 2015-12-16
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the glass transition temperature of organic small molecule compounds is low, and the material is extremely easy to crystallize, resulting in

Method used

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  • Derivative of dibenzofuran and preparation method and application thereof
  • Derivative of dibenzofuran and preparation method and application thereof
  • Derivative of dibenzofuran and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of embodiment one precursor 1

[0037] The reaction scheme is as follows:

[0038]

[0039] 149.6g (0.8mol) p-bromoanisole, 108.3g (0.88mol) p-methoxyaniline and 107.5g (1.2mol) potassium tert-butoxide were successively added to a 2L three-necked flask to obtain mixture I, and to mixture I was added 800g toluene, through N 2 After replacement for 10 min, 0.9 g (0.004 mol) of palladium acetate and 1.62 g (0.008 mol) of tri-tert-butylphosphine were added, and the mixture was refluxed at 110° C. for 5 hours. The reaction was quenched by adding water, separated, extracted, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was recrystallized from a mixed solvent of toluene and ethyl acetate (mass ratio 3:1) to obtain 119 g of light yellow solid with a yield of 64.9%. GC-MS: C 14 h 15 NO 2 : Calculated value: 229.11, Measured value [M] + = 229.27.

Embodiment 2

[0040] The preparation of embodiment two precursor 2

[0041] The reaction scheme is as follows:

[0042]

[0043] Synthesis of Intermediate 1:

[0044] Add 20g (0.06mol) 4,4'-dibromodiphenylamine and 13.1g (0.06mol) (BOC) to a 500mL three-necked flask 2 O, mix well to obtain mixture II, add 100g THF (tetrahydrofuran) to the above mixture II, and protect with nitrogen. Add 0.75g (0.006mol) DMAP (4-dimethylaminopyridine) to the system, and react at 65°C for 2h. After the reaction was completed, the temperature was lowered to 20-25° C., and the solvent was removed under reduced pressure to obtain a brown oil, which was filtered through a silica gel column to obtain 51.6 g of a white solid with a yield of 98%. LC-MS: C 17 h 17 Br 2 NO 2 , calculated value: 424.96, measured value: [M+2] + = 427.13.

[0045] Synthesis of Intermediate 2:

[0046] Add 42.7 g (0.1 mol) of intermediate 1 and 50.4 g (0.22 mol) of precursor 1 (prepared by Example 1) into a 2 L three-necked f...

Embodiment 3

[0049] The preparation of embodiment three precursor 3

[0050] The reaction scheme is as follows:

[0051]

[0052] Synthesis of intermediate 3:

[0053] The feed ratio and preparation process are the same as the synthesis of intermediate 1. 15.1 g of white solid was obtained with a yield of 95%. LC-MS: C 17 h 12 BrNO 2 , calculated value: 422.95, measured value: [M+2] + = 425.11.

[0054] Synthesis of Intermediate 4:

[0055] Add 2.4 g (0.01 mol) of intermediate 3 and 5.0 g (0.022 mol) of precursor 1 (prepared by Example 1) into a 100 mL three-necked flask to obtain mixture V. Add 50 g of toluene to the mixture V, and protect it with nitrogen. Then add 2.4g (0.025mol) sodium tert-butoxide, 0.29g (4×10 -4 mol)Pd(dppf)Cl 2 , 0.24g (8×10 -4 mol) tri-tert-butylphosphine tetrafluoroborate, mix well, turn on the mechanical stirring, and react at 110°C for 3h. After the reaction was completed, the temperature of the system was lowered to 20-25° C., suction filtered,...

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Abstract

The invention relates to a derivative of dibenzofuran and a preparation method and application thereof. The preparation method of the derivative of the dibenzofuran comprises the steps that carbon-nitrogen coupling is performed on p-bromoanisole and p-methoxyaniline to obtain a first precursor; a two-step reaction is performed on the first precursor and 4,4'-dibromodiphenylamine protected by butyloxycarbonyl to obtain a second precursor, and a two-step reaction is performed on the first precursor and 3,6-dibromocarbazole protected by butyloxycarbonyl to obtain a third precursor; carbon-nitrogen coupling is performed on all the precursors and 2,8-dibromodibenzofuran under the action of a palladium catalyst to obtain the derivative of the dibenzofuran. The prepared derivative of the dibenzofuran is easy to synthesize, low in cost, high in glass transition temperature and good in heat stability, is a hole-transport material with the good properties and has the good effect when the derivative is applied to perovskite solar cells.

Description

technical field [0001] The invention relates to a derivative of dibenzofuran, its preparation method and application, and relates to the field of solar cells. Background technique [0002] In recent years, a new solar cell based on organic / inorganic composite perovskite materials has attracted great attention from the international academic community due to its high conversion efficiency, simple preparation process of liquid / gas phase, and extremely low processing cost. . At present, perovskite solar cells have become one of the important research hotspots in the field of photovoltaics (Electronic Components and Materials, 2014, 33(8)). [0003] In the device structure of perovskite solar cells, the hole transport material is an important component, which plays the role of transporting holes. At first, perovskite solar energy used liquid electrolytes, but the liquid electrolytes were prone to leakage and packaging was difficult; and the perovskite layer was easily decompos...

Claims

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Application Information

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IPC IPC(8): C07D307/91C07D405/14H01L51/46
CPCC07D307/91C07D405/14H10K85/649H10K85/653H10K85/631H10K30/00Y02E10/549H10K85/636H10K85/50
Inventor 任辉彩庞茂印杨福山田绍振史汝金胡葆华
Owner VALIANT CO LTD
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