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A kind of carbazole diarylamine dendritic compound and its preparation method and application

A carbazole diarylamine and compound technology, which is applied in the field of carbazole diarylamine dendrimers and their preparation, can solve the problems of deformation, easy decomposition of materials, low glass transition temperature, etc., and achieves improved hole transport. performance, good effect, effect of improving amorphous properties

Active Publication Date: 2018-03-23
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, researchers have done more research on perovskite absorbing layers and electron transport layers, but there are few reports on hole transport materials, and the glass transition temperature of most materials is low, which makes the materials prone to decomposition, deformation, etc.

Method used

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  • A kind of carbazole diarylamine dendritic compound and its preparation method and application
  • A kind of carbazole diarylamine dendritic compound and its preparation method and application
  • A kind of carbazole diarylamine dendritic compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 Preparation of Compound 1

[0055] The reaction route is as follows:

[0056]

[0057] Respectively through the following three schemes:

[0058] Solution 1: Add 23g (0.07mol) 3,6-dibromocarbazole and 23g (0.10mol) (BOC) to a 250mL three-necked flask 2 O, mix well to obtain mixture I, add 90g THF to the above mixture I, protect with nitrogen, stir mechanically, the system is completely dissolved, and the system is brown and clear at this time. 1.7g (0.014mol) DMAP was added to the system, after 5 minutes of adding, a lot of bubbles were generated, and the system became brown and clear. At this time, the oil bath was heated to 70°C, and the system was refluxed for 2h. After the reaction was completed, the temperature was reduced to 20-25°C, and the solvent was removed under reduced pressure to obtain 30.6 g of brown oil. It was dissolved in dichloromethane, filtered through a silica gel column, and rinsed with dichloromethane to obtain 28.9 g of white solid with a y...

Embodiment 2

[0061] Example 2 Preparation of Compound 2

[0062] The reaction route is as follows:

[0063]

[0064] Respectively through the following three schemes:

[0065] Scheme 1: Add 25.0g (0.058mol) of compound 1 (prepared by Scheme 1 of Example 1), 28.3g (0.12mol) 4,4'-dimethoxydiphenylamine, 17.0g into a 500mL three-necked flask (0.17mol) Sodium tert-butoxide, mix well to obtain mixture II, add 250g of toluene to mixture II, pass nitrogen protection, turn on mechanical stirring, stir evenly, the system is brown solution, add 0.53g (2.35×10 -3 mol) Palladium acetate and 0.95g (4.70×10 -3 mol) tri-tert-butyl phosphine, heated to 65°C, and reacted for 4 hours. After the reaction is completed, add 100ml of water to quench the reaction, stir for 15min, stand still for layering, extract the lower aqueous phase with 50g of toluene, combine the organic phases, and wash twice with water to pH=7, each time with 100ml of water, 15g of anhydrous Na 2 SO 4 Dry, filter on a silica gel column, rinse ...

Embodiment 3

[0068] Example 3 Preparation of Compound 3

[0069] The reaction route is as follows:

[0070]

[0071] Respectively through the following three schemes:

[0072] Scheme 1: Add 31.1g (0.043mol) of compound 2 (prepared by Scheme 1 of Example 2) and 14.5g (0.129mol) of potassium tert-butoxide into a 1L three-necked flask, and mix well to obtain mixture Ⅲ. Add 620g of toluene to Ⅲ, turn on stirring, heat to 100°C, after 1 hour of reaction, the reaction is completed, down to 20-25°C, add 300g of water to quench the reaction, separate layers, 200g of ethyl acetate to extract the aqueous phase, and combine the organic phases , Dry with anhydrous sodium sulfate, remove the solvent under reduced pressure to obtain 31.3g dark green solid, 260g of methylene chloride dissolve the dark green solid, pass through a silica gel column, dichloromethane elution, remove the solvent under reduced pressure to obtain 28.3g yellow solid, toluene Recrystallized with a mixed solvent of n-hexane (mass ratio...

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Abstract

The present invention relates to a kind of carbazole diarylamine dendritic compound and its preparation method and application, the preparation method of described carbazole diarylamine dendritic compound comprises halogenated 9,9'-spirobifluorene, catalyst, The carbazole diarylamine compound is mixed with an organic base, and xylene is used as a solvent, reacted under the protection of an inert gas, recrystallized and purified, and a carbazole diarylamine dendritic compound shown in the following formula is obtained. The carbazole diarylamine dendritic compound prepared by the present invention has a simple process and a refining method, is very suitable for industrial production, has good thermal stability and morphological stability, and is used as a hole transport material for a perovskite solar cell. It has high photoelectric conversion efficiency.

Description

Technical field [0001] The invention provides a carbazole diarylamine dendritic compound and a preparation method and application thereof, and belongs to the field of solar cells. Background technique [0002] In recent years, a new type of all-solid-state planar solar cell-perovskite solar cell has attracted the attention of the international academic community due to its high conversion efficiency, simple preparation process such as liquid / gas phase, and extremely low processing cost. . At present, perovskite solar cells have become one of the important research hotspots in the photovoltaic field. [0003] The general structure of a perovskite solar cell is: metal anode / hole transport layer / perovskite absorption layer / electron transport layer / FTO. At present, scientific researchers have done more research on perovskite absorption layer and electron transport layer, but there are few reports on hole transport materials, and the glass transition temperature of most materials is l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/88H01L51/42H01L51/46
CPCC07D209/88H10K85/624H10K85/636H10K85/631H10K85/6572H10K30/151Y02E10/549Y02P70/50
Inventor 任辉彩杨福山史汝金庞茂印胡臻玉胡葆华
Owner VALIANT CO LTD
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