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Conjugated organic small molecule as well as preparation method and application thereof

A small molecule, organic technology, applied in the field of conjugated organic small molecules and their preparation, can solve the problems of backward development of small molecule donor materials, and achieve the effect of realizing electron mobility, improving photovoltaic performance, and improving miscibility

Pending Publication Date: 2022-07-08
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although compared with polymer donor materials, organic small molecule materials are simpler in structure and easier to prepare, modify and optimize, but the development of small molecule donor materials lags behind that of polymer donor materials. The efficiency of the solar cell (ASM-OSC) is 16.28%, therefore, the development of an all-small molecule OSC with high PCE has become one of the important challenges currently facing

Method used

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  • Conjugated organic small molecule as well as preparation method and application thereof
  • Conjugated organic small molecule as well as preparation method and application thereof
  • Conjugated organic small molecule as well as preparation method and application thereof

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preparation example Construction

[0058] see figure 1 As shown, another embodiment of the present invention provides a method for preparing a conjugated organic small molecule, comprising:

[0059] Dissolve the first compound, the second compound and tetrakistriphenylphosphine palladium in a solvent, and react at 110° C. for 12 h under inert gas protection and dark conditions to obtain an intermediate product;

[0060] Dissolving the intermediate product, the third compound, and piperidine in chloroform, and reacting at 65° C. for 8 hours under the protection of inert gas to obtain a conjugated organic small molecule;

[0061] Wherein, the structural formula of the first compound is:

[0062]

[0063] The structural formula of the second compound is:

[0064]

[0065] The structural formula of the third compound is:

[0066]

[0067] In the specific embodiment, the first compound, the second compound and tetrakistriphenylphosphine palladium are added to the reaction vessel, and then toluene is used...

Embodiment 1

[0081] The purpose of this embodiment is to prepare a conjugated organic small molecule, comprising the following steps:

[0082] In a 100 mL three-necked flask, compound 1 (454 mg, 0.5 mmol), compound 2 (622 mg, 1.25 mmol), tetrakistriphenylphosphonium palladium (Pd(PPh) were added in turn 3 ) 4 , 58 mg, 0.05 mmol), and then 30 mL of toluene (Toluene) was used as a solvent, under argon protection, and heated at 110° C. and refluxed for about 12 hours in the dark. The reaction solution after the reaction was poured into water, extracted with chloroform, washed with deionized water, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to obtain a crude product. The crude product was obtained by column chromatography (petroleum ether: chloroform=1:2) to obtain a black solid P1 (472.2 mg) in a yield of ~67%. The obtained P1 (191 mg, 0.135 mmol), compound 3 (272 mg, 1.35 mmol), 20 mL of chloroform (CHCl) 3 ) and a few drops of piperidine (pipe...

Embodiment 2

[0086] The purpose of this embodiment is to prepare a conjugated organic small molecule, comprising the following steps:

[0087] P1 (283 mg, 0.2 mmol) obtained in Example 1, compound 4 (435 mg, 2.0 mmol), 30 mL of chloroform and a few drops of piperidine were successively added to a 100 mL three-necked round-bottomed flask, and heated under argon protection. Reflux at 65°C for about 8 hours. The reaction solution after the reaction was concentrated under reduced pressure, was deposited in a large amount of methanol, and the obtained solid crude product was subjected to column chromatography (petroleum ether: chloroform=1.5:1) to obtain black solid BDF-2 (313 mg), The yield was 86%.

[0088] The synthetic route of the preparation method of the conjugated organic small molecule BDF-2 described in this example is as follows:

[0089]

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Abstract

The invention provides a conjugated organic small molecule as well as a preparation method and application thereof, and relates to the technical field of photoelectric materials. According to the conjugated small organic molecule, benzodifuran is used as a central electron donating (D) unit, terthiophene or thienothiophene bithiophene is used as a pi bridge, rhodanine or cyanoacetate is used as an end group electron withdrawing (A) unit, and the conjugated small organic molecule with an A-pi-D-pi-A type structure is constructed. Compared with the prior art, the conjugated small organic molecule can have enough voltage with the acceptor to drive exciton dissociation and complement the absorption spectrum of the acceptor, so that the energy conversion efficiency of the organic solar cell is improved, and the conjugated small organic molecule has relatively high thermal stability.

Description

technical field [0001] The invention relates to the technical field of optoelectronic materials, in particular, to a conjugated organic small molecule and a preparation method and application thereof. Background technique [0002] With the continuous development of economy and society, people's demand for energy is getting higher and higher, and traditional fossil energy cannot be regenerated in a short time, so it is imperative to develop new energy. Among the existing solar cells, organic solar cells (OSCs) are one of the most promising technologies for the production of low-cost energy due to their light weight, wide material sources, strong tunability of energy levels and absorption spectra, translucency, etc. advantage. Due to these excellent properties, in the past decades, a large number of researchers have been attracted to study how to improve the power conversion efficiency (PCE) of organic solar cell devices. In recent years, with the rapid development of non-fu...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D493/04H01L51/46H01L51/48
CPCC07D519/00C07D493/04H10K71/12H10K85/656H10K85/655H10K85/6576H10K85/6574Y02P70/50
Inventor 葛子义李丹丹杨道宾彭瑞祥
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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