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Non-fullerene acceptor material as well as preparation method and application thereof

A technology of non-fullerene acceptors and acceptor materials, applied in the field of non-fullerene acceptor materials, can solve the problems of complex synthesis and difficult structure adjustment of non-fullerene acceptor materials, and achieve good solubility, electronic The effect of high mobility

Active Publication Date: 2021-09-24
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention lies in the complex synthesis and difficulty in structural adjustment of non-fullerene acceptor materials in the prior art, thus providing a non-fullerene acceptor material, its preparation method and application

Method used

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  • Non-fullerene acceptor material as well as preparation method and application thereof
  • Non-fullerene acceptor material as well as preparation method and application thereof
  • Non-fullerene acceptor material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Embodiment 1: the synthesis of compound Me-BT

[0094]

[0095] Step 1: Synthesis of Compound 2-1

[0096] Magnesium chips (2.92g, 120mmol) were added to a 250mL three-necked bottle, the argon gas was replaced three times, a grain of iodine was added to the bottle under argon flow, and then 30mL of anhydrous tetrahydrofuran was added. Mesitylbromobenzene (23.89g, 120mmol) was dissolved in 60mL of anhydrous tetrahydrofuran, and 20mL of the solution was first added to the reaction system, and the reaction was initiated by heating until the reaction liquid became colorless, and the reaction initiation was completed, and continued in a slightly boiling state. Add the remaining solution dropwise, heat to reflux after the dropwise addition to complete the reaction of magnesium, and cool down for later use. Take another 250mL three-necked bottle, add palladium acetate (269.4mg, 1.2mmol) and 2-dicyclohexylphosphino-2'-(N,N-dimethylamine)-biphenyl (2.29g, 4.8mmol) to it and ...

Embodiment 2

[0113] Embodiment 2: the synthesis of compound i-Pr-BT

[0114]

[0115] Step 1: Synthesis of compounds 2-6

[0116]In the 500mL three-necked flask, add triisopropylbromobenzene (14.16g, 50mmol), 3-thiophene boronic acid (12.80g, 100mmol), potassium phosphate (21.23g, 100mmol), tridibenzylideneacetone dipalladium (458mg, 0.5mmol) and 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (821mg, 2mmol), the argon gas was replaced three times, and 100mL anhydrous toluene and 100mL anhydrous tetrahydrofuran were added as solvents, and three liquid Nitrogen freezing-pumping-thawing cycle removes dissolved oxygen in the solvent and heats to reflux for reaction. The reaction was monitored by TLC, and the developing solvent was petroleum ether. Extracted with dichloromethane, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography with petroleum ether as the eluent to obtain 14.10 g of compound 2-6 as a ...

Embodiment 3

[0133] Embodiment 3: the synthesis of compound i-Pr-IC and i-Pr-IC-F

[0134]

[0135] Step 1: Synthesis of Compound 2-11

[0136] Add compound 2-8 (1.14g, 2mmol), 30mL 1,2-dichloroethane and 1.9mL phosphorus oxychloride to a 100mL three-necked flask, add 1.6mL N,N-dimethylformamide dropwise, and heat Reflux reaction for 24h. After the reaction was complete, it was extracted with dichloromethane, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography. The eluent used was petroleum ether:dichloromethane=1:1, and compound 2- 11 Yellow solid 970.0 mg, yield 77.4%.

[0137] 1 H NMR (400MHz, CDCl 3 )δ: 9.74(s,1H),7.39(s,1H),7.14(s,2H),3.00(p,J=6.9Hz,1H),2.48(p,J=6.9Hz,2H),1.35( d,J=6.9Hz,6H),1.05(t,J=6.8Hz,12H).MS(EI)m / z:627.3(M+H + ).

[0138] Step 2: Synthesis of Compounds i-Pr-IC and i-Pr-IC-F

[0139]Add compound 2-11 (200 mg, 0.32 mmol), 30 mL chloroform, and 1.9 mL pyridine into a 10...

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Abstract

The invention discloses a non-fullerene acceptor material as well as a preparation method and application thereof. The non-fullerene acceptor material has a structure as shown in a formula (I). The non-fullerene acceptor material provided by the invention can have a non-condensed ring structure, and can maintain the planarity of a molecular host while ensuring the dissolving property, so that organic photovoltaic material molecules can be flexibly constructed by using a non-condensed ring structure unit, the material solubility is good, the light absorption range can be expanded to a near-infrared region, the electron mobility is high, and the development of novel efficient donor and acceptor materials is facilitated.

Description

technical field [0001] The invention relates to a non-fullerene acceptor material, its preparation method and application. Background technique [0002] In order to solve the increasingly acute energy problems, the scientific and efficient use of clean energy such as solar energy has become an important research topic. As one of the effective ways to use solar energy, organic solar cells have the advantages of light weight, flexibility, and easy processing. Widespread interest in science and industry. [0003] At present, high-efficiency organic solar cells in this field generally adopt bulk heterojunction structure, and the active layer is formed by mixing donor and acceptor materials. The donor material is a p-type organic / polymer semiconductor material, the system is rich in electrons, and has the ability to provide electrons and transfer holes. The acceptor material is an n-type organic semiconductor material that has the ability to accept and transfer electrons. In r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24C07D333/22C07D417/14H01L51/46H01L51/42
CPCC07D333/24C07D417/14C07D333/22H10K85/655H10K85/626H10K85/657H10K30/00Y02E10/549
Inventor 李维实薛中鑫许子文刘丽娜张翟
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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