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Polythiophene derivative photoelectric material, and preparation method and application thereof

A technology of polythiophene derivatives and optoelectronic materials, applied in circuits, electrical components, electrical solid devices, etc., can solve the problems of low open-circuit voltage short-circuit current, high HOMO energy level, insufficient absorption spectrum, etc., achieving easy synthesis, high Absorption coefficient, satisfying the effect of high-efficiency devices

Inactive Publication Date: 2019-05-28
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of P3HT is that the HOMO energy level is too high and the absorption spectrum is insufficient, resulting in a lower open circuit voltage (V oc ) and short circuit current (J sc )

Method used

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  • Polythiophene derivative photoelectric material, and preparation method and application thereof
  • Polythiophene derivative photoelectric material, and preparation method and application thereof
  • Polythiophene derivative photoelectric material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] This embodiment provides a monomer M1 and its preparation method.

[0057] The preparation of monomer M1 before polymerization, the reaction formula is as follows:

[0058]

[0059] (1) Dissolve 10mmol of 3-alkylthiophene in 50mL of tetrahydrofuran, add 10mmol of N-bromosuccinimide as a bromination reagent, stir at room temperature for 8h, separate and purify with silica gel chromatography to obtain 2-bromosuccinimide -3-Alkylthiophene.

[0060] (2) 5 mmol of 2-bromo-3-alkylthiophene, 0.5 mmol of bis(cyanobenzene)palladium dichloride, 10 mmol of silver nitrate and 10 mmol of potassium fluoride were added to a 100 mL two-necked flask, After the ventilation was completed, 50 mL of ultra-dry dimethyl sulfoxide was added, and the reaction was heated at 60°C. When the reaction was carried out for 3h and 6h, 10mmol of silver nitrate and potassium fluoride were added respectively, and the reaction was continued for 12h. After the reaction, cool to room temperature, pour ...

Embodiment 2

[0063] This embodiment provides a monomer M2 and its preparation method.

[0064] The preparation of monomer M2 before polymerization, reaction formula is as follows:

[0065]

[0066] (1) Dissolve 10mmol of 3-alkylthiophene in 50mL of N,N-dimethylformamide, add 10mmol of N-bromosuccinimide as a bromination reagent, stir at room temperature for 4h, and use silica gel Separation and purification by chromatographic column to obtain 2-bromo-3-alkylthiophene.

[0067] (2) Add 5mmol of 2-bromo-3-alkylthiophene, 0.05mmol of bis(cyanobenzene)palladium dichloride and 10mmol of silver fluoride into a 100mL two-necked flask, and add 50mL of ultra-dry dimethyl sulfoxide was heated at 80°C for 12h. After the reaction, cool to room temperature, pour the above reaction substance into 100 mL of water, extract three times with dichloromethane, dry the organic phase with anhydrous magnesium sulfate, and separate and purify with silica gel chromatography to obtain the monomer M2.

[0068]...

Embodiment 3

[0070] This embodiment provides a monomer N and its preparation method.

[0071] The preparation of monomer N before polymerization, the reaction formula is as follows:

[0072]

[0073] (1) Carry out Stille coupling reaction with 10mmol of 5,5'-dibromo-2,2'-bithiophene and 24mmol of tributyl(4-alkylthiophen-2-yl)tin, the specific operation is: The two reaction substrates and 0.4 mmol catalyst tetrakis(triphenylphosphine) palladium were added into a 100 mL two-necked flask, and 50 mL of distilled toluene was added as the reaction solvent after the ventilation was completed, and the reaction was heated under reflux for 12 h. After the reaction was completed, it was cooled to room temperature, and the above reaction substance was poured into 100 mL of water, extracted three times with dichloromethane, and the organic phase was dried with anhydrous magnesium sulfate, separated and purified by silica gel chromatography.

[0074] (2) The product obtained in the first step is br...

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Abstract

The invention belongs to the technical field of a photoelectric material and application, and particularly relates to a polythiophene derivative photoelectric material, and a preparation method and application thereof. Through the material, the density of polythiophene derivative alkyl side chains is reduced; electron withdrawing groups are introduced for reducing the HOMO energy grade, so that the regulation and control on the polymer energy grade, the dissolution performance, the aggregation and the crystallinity can be realized through changing different reactant proportioning ratio. Compared with P3HT, the material has the advantages that the crystallinity is improved; the adsorption spectrum generates red shift to a certain degree. The structure is simple; different repeated units arerealized; the synthesis is easy; the material is suitable for large-area production. In addition, the polythiophene derivative has the high absorption coefficient (105cm<-1>); the absorption capability on the sun light is enhanced; the requirements of a high-efficiency device can be met; the polythiophene derivative photoelectric material can be applied to the field of photoelectric materials oforganic solar batteries, perovskite solar batteries, organic thin film transistor and the like. The formula is shown in description.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and in particular relates to a polythiophene derivative photoelectric material and its preparation method and application. Background technique [0002] In recent years, with the gradual reduction of fossil fuel reserves and the increasing environmental problems caused by the use of fossil fuels, the development of renewable energy is imminent. Photovoltaic technologies such as solar cells, which directly convert solar energy into electricity, are considered to be one of the most promising solutions to these pressing problems. Silicon-based solar cells are by far the most mature photovoltaic technology, with high energy conversion efficiencies exceeding 25%. However, the high cost of silicon-based solar cells has limited their widespread commercialization. In contrast, polymer solar cells, which can achieve large-area and flexible device fabrication by solution ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/00H10K99/00
Inventor 段春晖贾小娥黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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