Polythiophene as well as preparation method and application thereof

A technology of polythiophene and polymerization reaction, which is applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc. It can solve problems such as difficulty in regulation and backward device performance, and achieve low manufacturing cost, improved device performance, and high yield. Effect

Pending Publication Date: 2022-04-12
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the high highest occupied molecular orbital (HOMO) energy level and the difficult-to-tunable morphology of the photoactive layer, the device performance of polythiophene-based organic solar cells lags far behind that of the conjugated polymerization of alternating donor-acceptor copolymerization. thing

Method used

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  • Polythiophene as well as preparation method and application thereof
  • Polythiophene as well as preparation method and application thereof
  • Polythiophene as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 3-cyanothiophene-based monomer M1:

[0037]

[0038] The synthetic route is as follows:

[0039]

[0040] (1) Synthesis of intermediate 3

[0041] Intermediate 1 (2.00g, 7.50mmol) was added to a dry reaction flask, reactant 2 (13.43g, 22.48mmol) was added, catalyst Pd (PPh 3 ) 4 (0.43g, 0.37mmol), in N 2 Add an appropriate amount of anhydrous N,N-dimethylformamide to dissolve under protection, and react overnight at 80°C. The reaction was quenched by adding water, then extracted, concentrated, dried, and separated by column chromatography to obtain a bright yellow oily product with a yield of 93%.

[0042] (2) Synthesis of monomer M1

[0043] Add intermediate 3 (2.50g, 3.46mmol) into a dry reaction flask, add appropriate amount of chloroform and acetic acid to dissolve, and slowly add N-bromosuccinimide (1.23g , 6.92mmol), slowly rise to room temperature, thin-layer chromatography (TLC) monitors the reaction process, after the reaction is comp...

Embodiment 2

[0045] Preparation of 3-cyanothiophene-based monomer M2:

[0046]

[0047] The synthetic route is as follows:

[0048]

[0049] (1) Synthesis of Intermediate 5

[0050]Intermediate 1 (1.00g, 3.75mmol) was added to a dry reaction flask, reactant 4 (7.35g, 11.24mmol) was added, catalyst Pd (PPh 3 ) 4 (0.17g, 0.15mmol), in N 2 Add an appropriate amount of anhydrous N,N-dimethylformamide to dissolve under protection, and react overnight at 80°C. The reaction was quenched by adding water, then extracted, concentrated, dried, and separated by column chromatography to obtain a bright yellow oily monomer with a yield of 95%.

[0051] (2) Synthesis of monomer M2

[0052] Add intermediate 5 (1.97g, 2.36mmol) into a dry reaction flask, add appropriate amount of chloroform and acetic acid to dissolve, and slowly add N-bromosuccinimide (0.84g , 4.72mmol), slowly rose to room temperature, TLC monitored the degree of reaction, quenched with water after the completion of the react...

Embodiment 3

[0054] Preparation of 3-cyanothiophene-based monomer M3:

[0055]

[0056] The synthetic route is as follows:

[0057]

[0058] (1) Synthesis of Intermediate 7

[0059] In a 250mL double necked round bottom flask, under N 2 Under protection, magnesium turnings (2.4 g, 100 mmol) and a small amount of iodine were dissolved in 150 mL of anhydrous THF. Slowly add 5-bromo-1-pentene (11.9g, 80mmol), stir for 20 minutes, then raise the temperature to 80°C and continue the reaction for 2.5 hours, then cool to 0°C and slowly add the above reaction solution dropwise to compound 6 (12.2 g,75mmol), Ni(dppp) 2 Cl 2 (100mg) in a round bottom flask. The reaction was continued for 12 hours at room temperature. After the reaction was completed, it was quenched by adding water, then extracted, concentrated, dried, and separated by column chromatography to obtain a light yellow oily monomer with a yield of 80%.

[0060] (2) Synthesis of Intermediate 8

[0061] In a 250 mL two-neck ...

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Abstract

The invention belongs to the technical field of organic photoelectricity, and particularly relates to polythiophene as well as a preparation method and application thereof. The structural formula of the polythiophene provided by the invention is as shown in formula I in the specification. An electron-withdrawing functional group cyano group is introduced into a conjugated main chain of polythiophene, so that intermolecular pi-pi accumulation is promoted, and the crystallinity of the polymer is enhanced. The polythiophene provided by the invention has good crystallinity and photoelectric property, and excellent light absorption and carrier transport performance, and can realize higher energy conversion efficiency in an organic solar cell. More importantly, the polythiophene provided by the invention has the advantages of simplicity in synthesis, easiness in structure modification, convenience in preparation of derivative compounds and the like. Based on the advantages, the polythiophene provided by the invention is expected to become an important organic semiconductor material and is used for constructing organic photovoltaic devices with low cost, high performance and new functions.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to the preparation of a class of organic photoelectric materials of polythiophene and its derivatives and organic photovoltaic devices using the derivatives. Background technique [0002] Organic solar cells have attracted much attention due to their significant advantages such as light weight, low cost, diverse structures, good controllable performance, simple preparation process, and flexible devices can be prepared by solution processing. With the vigorous development of organic photoelectric materials, the highest energy conversion efficiency of organic solar cells has exceeded 18%. However, most of the current high-performance polymer donors have complex synthesis routes and tedious purification steps, resulting in high cost and difficulty in large-scale production, which greatly limits the commercialization of organic solar cells. Therefore, exploring ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 段春晖袁熙越曹镛
Owner SOUTH CHINA UNIV OF TECH
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