A kind of organic small molecule material containing benzodithiophene and its preparation method and application

A benzodithiophene and small molecule technology, applied in the field of organic solar cells, can solve the problems of weak absorption, affecting the improvement of organic solar cell devices, strong aggregation, etc., and achieve improved short-circuit current density, excellent device effect, and good thermal stability Effect

Active Publication Date: 2020-03-24
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, non-fullerene acceptor materials such as PDI and NDI have problems such as weak absorption and too strong aggregation, which affect the further improvement of organic solar cell devices.

Method used

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  • A kind of organic small molecule material containing benzodithiophene and its preparation method and application
  • A kind of organic small molecule material containing benzodithiophene and its preparation method and application
  • A kind of organic small molecule material containing benzodithiophene and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1, 4,8-bis((triisopropylsilyl)ethynyl)benzo[1,2-b:4,5-b']dithiophene (3).

[0041] A 250.0ml dry three-necked round-bottomed flask with a stirring bar was passed into argon, and under the protection of argon, compound 1 (ethynyltriisopropylsilane, 6.31g) and 75.0ml of dry THF were injected through a syringe. , the solution was clear and transparent, and then the reaction bottle was placed at -78°C for half an hour at a constant temperature, and n-BuLi (15.2ml, 2.5M) was added dropwise, and there was no obvious change during this process. After constant temperature reaction for 2.5hrs, add reactant 2 benzo[1,2-b:4,5-b']dithiophene-4,8-dione (grass green crystal, 2.54g), and slowly rise to room temperature React for 2.5hrs, add anhydrous SnCl 2 (17.50 g) was reacted overnight to finally obtain a light brown clear solution. During processing, the reaction liquid was directly transferred to a one-necked flask, and the solvent was spin-dried, and the column chromat...

Embodiment 2

[0042] Example 2, ((2,6-bis(trimethyltin)benzo[1,2-b:4,5-b']dithiophene-4,8-diyl)bis(alkyne-2,1 -diyl))bis(triisopropylsilyl)(4).

[0043] Weigh the reactant 3 (3.86g) in a 250.0ml dry two-necked round-bottomed flask with a stirrer, and pump it through a vacuum double-row tube three times each, and place it in a flask filled with argon protective gas. Add TMEDA (tetramethylethylenediamine, 3.25g) and dry THF (90.0ml), the solution is light yellow, stir at room temperature, after the solid reactants are completely dissolved, place the reaction solution at -78°C for half an hour , and then began to add n-BuLi (11.7ml, 2.5M) dropwise. When it was added dropwise to 8.0ml, the solution became turbid and a yellow solid was precipitated. After constant temperature reaction for 2.0hrs, inject Me with a syringe 3 SnCl (35.0ml, 1.0M), the solution became clear immediately, slowly rose to room temperature and reacted overnight. When processing, pour 100.0ml deionized water into the fla...

Embodiment 3

[0044] Example 3, 5,5'-(4,8-bis((triisopropylsilyl)ethynyl)benzo[1,2-b:4,5-b']dithiophene-2,6- Diyl)bis(4-(2-ethylhexyl)thiophene-2-carbaldehyde)(6).

[0045] Weigh compound 4 (2.0g, 2.28mmol) and 5-bromo-4-(2-ethylhexyl)thiophene-2-carbaldehyde (2.42g, 7.99mmol) in a 75.0ml dry pressure tube equipped with a stirring bar , add 60.0ml of dry toluene, and then bubble the long needle with argon for 15min to ensure that the pressure tube is exhausted and filled with argon inert gas. Then weigh the catalyst Pd (PPh 3 ) 4 (263.5mg, 10% eq) was quickly added to the pressure-resistant tube, and the long needle port stayed in the pressure-resistant tube for a period of time to ensure that the entire pressure-resistant tube was filled with argon gas, and the stopper was quickly covered and tightened, and then the reaction liquid It was heated to 110° C. under stirring and reacted overnight. After cooling to room temperature, transfer the reaction solution directly to a single-necked...

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Abstract

The invention discloses a small organic molecule material containing benzodithiophene and its preparation method and application. The material structure is as in formula I, A1 and A2 are electron-deficient conjugated units; π is a compound containing carbon-carbon double bonds or carbon-nitrogen The conjugate unit of the bond. The preparation of the material includes the following steps: synthesizing monomers containing acetylene silyl groups and aldehyde groups with benzodithiophene as the core through coupling reactions; The intermediate of the alkyne active group; carry out the Sonogashira coupling reaction between the intermediate containing the terminal alkyne active group and the A1 containing the halogenated group, and obtain the organic small molecule material containing the aldehyde functional group; the compound containing the aldehyde functional group The organic small molecule material is subjected to Knoevenagel condensation reaction with A2 under the catalysis of the base to obtain the target small molecule material. The material of the invention has broader and stronger absorption and good thermal stability, and is applied in organic photovoltaic devices.

Description

technical field [0001] The invention belongs to the technical field of organic solar cells, and in particular relates to a preparation method of an organic small molecule acceptor material containing benzodithiophene and its application in organic photovoltaic devices. Background technique [0002] Organic solar cells (OSCs) are currently one of the hotspots in the field of new materials and new energy. Area preparation of flexible devices and other advantages. Among them, fullerene and its derivatives (such as PC 61 BM and PC 71 The electron acceptor materials prepared by BM) have made a great contribution to the development of organic solar cells, but these materials also have their own defects, such as high cost of raw materials, difficulty in preparation and purification, narrow and weak absorption range in the visible light region, and poor compatibility with donors. Materials tend to aggregate when blended. Therefore, designing and synthesizing new non-fullerene ac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C07D519/00H01L51/42H01L51/46
CPCC07D495/04C07D519/00H10K85/655H10K85/626H10K85/6576H10K85/6572H10K30/30Y02E10/549
Inventor 黄飞谢锐浩应磊曹镛
Owner 东莞伏安光电科技有限公司
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