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A class of aromatic condensed rings substituted by siloxane group and its preparation method and application

A siloxane-based, aromatic technology with applications in chemical instruments and methods, silicon organic compounds, semiconductor/solid-state device manufacturing, etc.

Active Publication Date: 2021-11-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, at this stage, organic solar cells still have problems in many aspects such as stability, device efficiency, and large-area processability.

Method used

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  • A class of aromatic condensed rings substituted by siloxane group and its preparation method and application
  • A class of aromatic condensed rings substituted by siloxane group and its preparation method and application
  • A class of aromatic condensed rings substituted by siloxane group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1: Aromatic fused ring compound M substituted by siloxane group 1 Synthesis

[0068] m 1 The synthetic route of figure 2 shown. Concrete reaction steps and reaction conditions are as follows:

[0069]

[0070] Under nitrogen protection, A (2.66g, 10mmol) was dissolved in anhydrous dimethyl sulfoxide (50ml), potassium tert-butoxide (8.98g, 80mmol) was added three times, and reacted at 80°C for 1 hour. Then 5-bromopent-1-ene (11.92, 80 mmol) was added dropwise, and reacted at 85-90° C. for 12 hours. The reaction was quenched by adding water, extracted three times with ethyl acetate, and washed several times with distilled water. Using petroleum ether as the eluent, the product was further purified by silica gel chromatography to obtain a light yellow solid (3.23 g, yield 60%), namely compound C.

[0071] Under nitrogen protection, C (3.23g, 6mmol) and 1,1,1,3,5,5,5-heptamethyltrisiloxane (10.68g, 48mmol) were dissolved in anhydrous THF (50ml) , add 5 dr...

Embodiment 3

[0078] Embodiment 3: Formula M 3 The synthetic M of shown small organic molecule (i.e. specific compound shown in formula I ') 4 The synthetic route of Figure 4 shown. Concrete reaction steps and reaction conditions are as follows:

[0079]

[0080] Under nitrogen protection, compound D (2.32g, 1.32mmol) and compound N (1.69g, 5.30mmol) were placed in a two-necked flask, and dissolved in anhydrous o-xylene (30ml), and then catalyst four (three Phenylphosphine) palladium (0) (76.5mg, 0.067mmol), react at 120°C overnight. The reactant was cooled to room temperature, and the solvent was dried with a rotary evaporator. Using petroleum ether / dichloromethane mixture as eluent, the product was purified by silica gel chromatography to obtain dark red solid N (1.11 g, 44%).

[0081] Under nitrogen protection, compound K (500 mg, 0.26 mmol) and compound H (483 mg, 2.10 mmol) were dissolved in chloroform (30 ml), added pyridine (1 ml), heated to reflux, and reacted overnight. Sub...

Embodiment 4

[0082] Example 4: Determination of UV-Vis Absorption of Molecules Using UV-Vis Spectrometer

[0083] For the small molecule M prepared in embodiment 2,3 2 , M 3 Chloroform solution and film absorption tests were performed. UV-Vis absorption spectrum such as Figure 5 shown.

[0084] m 2 , M 3 The optical absorption data are shown in Table 1. Wherein, a) is measured in the chloroform solution; b) is measured under the film state,

[0085]

[0086] As can be seen from the table, the small molecule M 2 The solution absorbs at 600-900nm, and the maximum molar extinction coefficient is 1.86×10 5 m -1 cm -1 ; The absorption red shift in the thin film state ranges from 600 to 1000nm, the absorption edge of the film reaches 1022nm, and the corresponding optical band gap is 1.21eV. It is a typical near-infrared small molecule and can be used as a narrow band gap acceptor in photovoltaic devices. small molecule M 3 The absorption range of the solution is in the range of...

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Abstract

The invention discloses a siloxane-substituted aromatic condensed ring, a preparation method and application thereof. The structure of the siloxane-substituted aromatic fused ring is shown in the formula, and the structure of the conjugated small molecule based on the siloxane-substituted aromatic fused ring is shown in the formula'. The method for preparing the above-mentioned siloxane group substituted aromatic fused ring and the organic small molecule acceptor based on this structure provided by the present invention has simple synthesis process, convenient operation, high product yield, and the obtained compound has correct structure and stability through instrument detection. it is good. The organic small molecules based on siloxane-based substituted aromatic fused rings prepared by the present invention have strong absorption of sunlight in the visible and near-infrared regions, and have suitable electronic energy levels, and can be used as n-type narrow-bandgap electron acceptor materials , can be used with wide, medium bandgap P-type polymers or small molecule donors for organic solar cells.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic materials, and in particular relates to a siloxane-substituted aromatic condensed ring structural unit and a preparation method and application thereof. Background technique [0002] In recent years, new energy sources such as wind energy, water energy, tidal energy, and solar energy have been more and more welcomed and valued by human society due to their rich resources, clean and pollution-free characteristics. As an emerging solar technology, organic solar cells have received extensive attention from scientific researchers. Compared with traditional inorganic solar cells, organic solar cells have a series of advantages such as low production cost, light weight, flexible devices, and large-area devices through roll-to-roll rapid processing. In the past two decades, through the unremitting efforts of scientific researchers, especially in the continuous exploration of active layer materials, p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08H01L51/42H01L51/46
CPCC07F7/0838C07F7/0889H10K85/626H10K85/655H10K85/6576H10K85/40H10K30/00Y02E10/549
Inventor 陈军武李素晗邱日杭
Owner SOUTH CHINA UNIV OF TECH
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