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Bridged asymmetric benzodiazole and/or pyridine diazole double-acceptor polymer semiconductor, preparation method and application thereof

A technology of benzodiazoles and pyridinediazoles, applied in the field of polymer semiconductor materials

Active Publication Date: 2021-01-29
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bridged asymmetric benzodiazoles and / or pyridinediazoles double acceptor polymer semiconductor materials have not been reported

Method used

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  • Bridged asymmetric benzodiazole and/or pyridine diazole double-acceptor polymer semiconductor, preparation method and application thereof
  • Bridged asymmetric benzodiazole and/or pyridine diazole double-acceptor polymer semiconductor, preparation method and application thereof
  • Bridged asymmetric benzodiazole and/or pyridine diazole double-acceptor polymer semiconductor, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] A kind of polymer semiconductor material whose chemical structure is PBT-fBTT, its synthetic route is as follows:

[0098]

[0099] (1) the chemical structure formula is the synthesis of the intermediate of a: under nitrogen protection, add tributyl-[4-(2-decyltetradecyl) thiophen-2-yl] alkyl tin (Suzhou Na Kai Technology Co., Ltd.) (5.8g, 8.2mmol), 4,7-dibromo-2,1,3-benzothiadiazole (2.0g, 6.8mmol), bis(triphenylphosphine) dichloride Palladium (0.24g, 0.34mmol) catalyst, 70mL toluene solvent. After reflux for 4 hours, cool to room temperature. Using dichloromethane for extraction, the organic phase was dried with magnesium sulfate, and the solvent was spin-dried to obtain a crude product. Then adopt silica gel chromatographic column purification to obtain the target product 4-bromo-7-(4-(2-decyltetradecyl)thiophen-2-yl)-benzene[c][1,2,5]thiazole, the yield = 85%.

[0100] The structural characterization data are as follows,

[0101] 1 H NMR (400MHz, CDCl 3 ),...

Embodiment 2

[0127] A kind of polymer semiconductor material whose chemical structure is PBT-PTT, its synthetic route is as follows:

[0128]

[0129] (1) Synthesis of an intermediate whose chemical structural formula is a: Synthesize with reference to the synthetic method of the above-mentioned Example 1.

[0130] (2) Synthesis of an intermediate whose chemical structural formula is b: under nitrogen protection, tributyl-[4-(2-decyltetradecyl)thiophen-2-yl]alkyltin (5.8g , 8.2mmol), 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine (2.0g, 6.8mmol), bis(triphenylphosphine)palladium dichloride (0.24g, 0.34mmol) catalyst, 70mL toluene solvent. After reflux for 4 hours, cool to room temperature. Using dichloromethane for extraction, the organic phase was dried with magnesium sulfate, and the solvent was spin-dried to obtain a crude product. Then use silica gel column purification to obtain the target product 7-bromo-4-(4-(2-decyltetradecyl)thiophen-2-yl)-[1,2,5]thiazole[3,4-c] Pyridine, yi...

Embodiment 1 and 2

[0152] The measurement of the spectroscopic properties of the polymer PBT-fBTT and PBT-PTT and polymer solar cell and organic photodetector properties prepared by above-mentioned embodiment 1 and 2:

[0153] (1) Absorption spectral properties of polymers PBT-fBTT and PBT-PTT

[0154] figure 1 UV-visible-near-infrared absorption spectra of polymer PBT-fBTT in chlorobenzene solution and thin film on quartz wafer. Depend on figure 1 It can be seen that both the polymer PBT-fBTT solution and the film exhibit a wide absorption range, and the maximum absorption sideband value of the film is about 835nm, and the corresponding optical band gap is 1.49eV (the optical band gap is calculated according to the formula E g =1240 / λ calculation, where E g is the optical bandgap, and λ is the maximum absorption sideband value of film absorption).

[0155] figure 2 UV-visible-near-infrared absorption spectra of polymer PBT-PTT in chlorobenzene solution and thin film on quartz wafer. Depe...

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Abstract

The invention belongs to the field of polymer semiconductor materials, and discloses a bridged asymmetric benzodiazole and / or pyridine diazole double-acceptor polymer semiconductor, a preparation method and application thereof. The structure of the polymer semiconductor is shown as a formula (I). The method provided by the invention is simple and efficient in synthetic route, low in development cost, high in universality and good in repeatability. A polymer solar cell and an organic light detector which are prepared by taking the bridged asymmetric benzodiazole and / or pyridine diazole double-acceptor polymer semiconductor reported by the invention as an active layer show excellent performance, and the energy conversion efficiency of the polymer solar cell is 7% or above; the dark current density of an organic photodetector is 10<-6>mA / cm<2> or below, so that the polymer semiconductor material has a wide market prospect in organic electronic devices like organic photovoltaics, logic complementary circuits, organic photodetectors, organic field effect transistors, organic light emitting diodes and the like.

Description

technical field [0001] The invention belongs to the field of polymer semiconductor materials, and relates to a polymer semiconductor bridging asymmetric benzodiazoles and / or pyridinediazoles double acceptors and a preparation method and application thereof. Background technique [0002] Over the past decade, polymer solar cells (PSCs) have made remarkable progress in improving the power conversion efficiency (PCE), such as developing high-performance polymer donor units, introducing efficient interface materials, and optimizing device structures. Although many high-performance polymeric donor materials have been reported, only a limited few of them are narrow-bandgap (NBG, <1.60eV) polymers. Compared with wide-bandgap and medium-bandgap polymers, narrow-bandgap polymers have strong and broad absorption in the near-infrared region, which makes them an important building block for building multicomponent and tandem solar cells. However, most of the reported narrow-bandgap ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/126C08G2261/414C08G2261/95C08G2261/91C08G2261/92C08G2261/124C08G2261/1412C08G2261/146C08G2261/3223C08G2261/3246C08G2261/3241H10K85/113H10K85/151Y02E10/549
Inventor 应磊朱春光钟知鸣黄飞曹镛
Owner 东莞伏安光电科技有限公司
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