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A conjugated small molecule semiconductor material containing halogen modified core group and its preparation and application

A small molecule and semiconductor technology, applied in the field of organic small molecule semiconductor materials and organic small molecule solar cells, can solve the problems of few application reports, and achieve the effects of high efficiency operation, good solubility and light absorption performance, large application potential and value

Active Publication Date: 2021-05-18
CHONGQING INST OF GREEN & INTELLIGENT TECH CHINESE ACADEMY OF SCI +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the application of this structural unit in small molecule donor materials, and there is a lot of room for development.
In addition, the new small molecule donor materials with fluorinated or chlorinated two-dimensional BDT as the core unit mainly use alkyl chain-modified tertiary thiophene as the π bridge unit, and no rigid bridge unit (such as BDD or structurally modified BDD unit) was reported as a π-bridged molecule

Method used

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  • A conjugated small molecule semiconductor material containing halogen modified core group and its preparation and application
  • A conjugated small molecule semiconductor material containing halogen modified core group and its preparation and application
  • A conjugated small molecule semiconductor material containing halogen modified core group and its preparation and application

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preparation example Construction

[0050] The preparation method of the conjugated small molecule semiconductor material containing halogen modified core group in the present invention comprises the following steps:

[0051] (1) Tin reagent reaction: dissolve raw material A in a dry organic solvent, under the protection of an inert gas, slowly drop in the hydrogen extraction reagent while stirring, stir and react, quickly add the tin reagent, slowly return to room temperature, and stir overnight , after the reaction is finished, the reaction solution is post-treated to obtain compound I;

[0052] (2) Still coupling reaction: dissolve compound I and raw material B in an organic solvent, add a catalyst, heat and stir the reaction under inert gas protection conditions, and post-process the reaction solution after the reaction to obtain compound II;

[0053] (3) Tin reagent reaction: Dissolve compound II in dry organic solvent F, under inert gas protection conditions, slowly drop in hydrogen extraction reagent whil...

Embodiment 1

[0082] Preparation of 2Cl-BDT-DD

[0083] (1) Preparation of compound I

[0084] Raw material A (3.0015g, 0.0178mol) was dissolved in dry tetrahydrofuran, stirred at -78°C, and slowly dropped into n-butyllithium tetrahydrofuran solution (7.85mL, 2.5mol·L -1 ), under the condition of nitrogen protection, keep stirring at -78°C for 1 hour, then quickly add the raw material trimethyltin chloride tetrahydrofuran solution (19.6mL, 1.0mol·L -1 ), slowly returned to room temperature, and stirred overnight. After the reaction is over, add water to stop the reaction, extract with ethyl acetate to obtain the upper organic phase, wash the organic phase with saturated potassium fluoride solution and water successively, collect the organic phase, add anhydrous MgSO 4 After drying, filtering, and rotary evaporation to remove the solvent of the filtrate, the crude product, Compound I (6.4155 g, 98.7%) was obtained, and the product could be subjected to the next reaction without further pur...

Embodiment 2

[0101] 2Cl-BDT-DD UV-Vis Absorption Spectrum

[0102] The target compound 2Cl-BDT-DD in embodiment 1 is made into 10 respectively -5 mol L -1 and 10 -2 mol L -1 chloroform solution, respectively measure the ultraviolet absorption of the solution and the film, wherein the film preparation uses a homogenizer 1200rpm to mix 10 -2 mol L -1 The solution was spin-coated on a quartz plate, and the scanning range was 200-1100 nm. The measuring instrument was a Perkin Eimer Lambda365 spectrophotometer. The UV-Vis absorption curves of compound 2Cl-BDT-DD in chloroform solution and film are as follows figure 2 As shown, the maximum absorption peaks of the solution are respectively at 272nm, 358nm and 492nm; the maximum absorption peaks of the film are respectively at 246nm, 384nm and 568nm. The large red shift of the film absorption shows the good packing and intermolecular force of 2Cl-BDT-DD molecules. In addition, the optical bandgap of 2Cl-BDT-DD can be estimated to be 1.77eV...

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Abstract

The invention discloses a conjugated small molecular semiconductor material containing a halogen-modified core group and its preparation and application. The small-molecule semiconductor material includes a halogenated two-dimensional thienothiophene core, a bridging unit and a hexylthiophene end group, and its preparation method is to recycle an organotin reagent reaction and Still coupling to obtain a target molecule, a total of seven steps of reaction: tin reagent Reaction, Still coupling reaction, tin reagent reaction, Still coupling reaction, tin reagent reaction, Still single-sided coupling reaction and Still double-sided coupling reaction, the three-step tin reagent reaction in the seven-step reaction all yields a crude product that does not need to go through the column Directly put into the next reaction, efficient and easy to operate. The small molecule semiconductor material of the present invention has a longer range of ultraviolet-visible absorption, deeper electron highest occupied orbital and lowest empty orbital, has good solubility and light absorption performance, and can be used as an electron donor material for small molecule organic solar cells .

Description

technical field [0001] The invention relates to the technical field of organic small molecule semiconductor materials and organic small molecule solar cells, in particular to the technical field of small molecule semiconductor materials, in particular to a conjugated small molecule semiconductor material containing a halogen-modified core group and a preparation method thereof. Background technique [0002] Organic semiconductor materials are rich in resources and have diverse and adjustable structures. They are the core materials in organic photovoltaic devices. Organic solar cells have become one of the most competitive development systems in the third generation of organic solar cells due to the advantages of light weight, flexibility, solution processing and low-cost large-area printing preparation. According to the active layer material of organic solar cells, organic solar cells can be divided into polymer organic solar cells and small molecule organic solar cells. Ov...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/655H10K85/6576Y02E10/549
Inventor 陈海燕肖泽云孙宽陆仕荣杨可付杰浩
Owner CHONGQING INST OF GREEN & INTELLIGENT TECH CHINESE ACADEMY OF SCI
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