A kind of derivative of dibenzofuran and its preparation method and application

A technology for dibenzofuran and derivatives is applied to the derivatives of dibenzofuran and the fields of preparation and application thereof. Production and other problems, to achieve the effect of favorable battery properties, high photoelectric conversion efficiency and low price

Active Publication Date: 2017-05-03
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 device instability and poor repeatability; the molecular weight of polymer materials is uncertain, and it is difficult to realize industrial production

Method used

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  • A kind of derivative of dibenzofuran and its preparation method and application
  • A kind of derivative of dibenzofuran and its preparation method and application
  • A kind of derivative of dibenzofuran and its preparation method and application

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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PUM

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Abstract

The present invention relates to a derivative of dibenzofuran and its preparation method and application. The preparation method of the derivative of dibenzofuran is obtained by coupling p-bromoanisole and p-methoxyaniline through carbon-nitrogen coupling Precursor 1; Precursor 1 and tert-butoxycarbonyl-protected 4,4'-dibromodiphenylamine are reacted in two steps to obtain precursor 2, precursor 1 and tert-butoxycarbonyl-protected 3,6-dibromocarbazole Precursor 3 is obtained through two-step reaction; the above precursor is respectively coupled with 2,8-dibromodibenzofuran under the action of palladium catalyst through carbon-nitrogen coupling to obtain a derivative of dibenzofuran. The derivatives of dibenzofuran prepared by the present invention are easy to synthesize, low in cost, high in glass transition temperature and good in thermal stability, and are excellent hole transport materials, which can be used in perovskite solar cells to obtain Had a good effect.

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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Patent Type & Authority Patents(China)
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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