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Narrow-band-gap n-type polymer acceptor and preparation method and application thereof

A polymer and compound technology, applied in the polymer field, can solve the problems of weak light response in the long wavelength direction and low short-circuit current in all-polymer battery devices, achieve high molar absorption coefficient and thermal stability, high filling factor, The effect of wide spectral response range

Active Publication Date: 2017-10-27
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the low molar absorptivity of N2200, the photoresponse in the long-wavelength direction of the prepared all-polymer battery device is weak, resulting in a low short-circuit current, which becomes a bottleneck for further improvement of its efficiency (Adv.Mater.2016,28, 8288)

Method used

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  • Narrow-band-gap n-type polymer acceptor and preparation method and application thereof
  • Narrow-band-gap n-type polymer acceptor and preparation method and application thereof
  • Narrow-band-gap n-type polymer acceptor and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1, the synthesis of formula IDIC-C16

[0073] Its reaction equation is as figure 1 shown. Concrete reaction steps and reaction conditions are as follows:

[0074]

[0075] Preparation of ID-CHO:

[0076] The preparation method of ID-CHO can be prepared by referring to the literature (Zhang Zhiguo, Li Yongfang, J.Am.Chem.Soc. 2016, 138, 15011), just replace m-IT with literature (J.Am.Chem. Soc 2010, 132, 11437) can be compound 7 (named ID in this patent) in the attached information. The specific method is as follows:

[0077] Take 2.32 g (2.0 mmol) of 4,9-dihydro-4,4,9,9-tetrakis(hexadecyl)-s-inda[1,2-b:5,6-b'] -Dithiophene (ID) was placed in a 100mL two-necked bottle under nitrogen protection. Add 30 mL of dry tetrahydrofuran to dissolve. The reaction flask was placed in acetone liquid nitrogen at -78°C. When the temperature of the reaction system dropped to -78°C, 4.4 mmol of n-butyllithium was added dropwise, and the acetone bath was removed after...

Embodiment 2

[0084] Example 2. Synthesis of polymer represented by formula IDIC-C16-Br

[0085] Its reaction equation is as figure 2 shown. Concrete reaction steps and reaction conditions are as follows:

[0086]

[0087]Take ID-CHO (0.9 g, 0.74 mmol) and IC-Br (1.0 g, 3.65 mmol, according to the literature Eur.J.Org.Chem.2016, 2016, 2404, Materials Chemistry Frontiers 2017, 1, 1389. Synthesized), This was dissolved in chloroform (50 mL), evacuated with argon for 5 minutes, 0.7 mL of pyridine was added, and the reaction was stopped after 8 hours at room temperature. The reaction solution was slowly precipitated into methanol (200 mL), the precipitated solid was filtered, rinsed with methanol, and vacuum-dried for one day to obtain 1.1 g of the compound represented by the formula IDIC-C16-Br as a powder, with a yield of 85.9% .

[0088] Structural corroboration data: 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 8.98-9.02(m, 2H), 8.75-8.86(m, 1H), 7.78-8.58(m, 5H), 7.70-7.80(s, 2H), 7.76-7.6...

Embodiment 3

[0091] Embodiment 3, the synthesis of polymer represented by formula PZ1

[0092] Its reaction equation is as image 3 shown. Concrete reaction steps and reaction conditions are as follows:

[0093]

[0094] Referring to the literature (Chem.Mater., 2012, 24(16), 3247-3254), take 0.02 mmol each of monomer IDIC-C16-Br and M1, dissolve it in a mixed solvent of toluene (8 mL) and DMF (2 mL) After that, the air was evacuated with argon for 5 minutes, the catalyst tetrakis(triphenylphosphine)palladium(0) (10 mg) was added, and the air was continued to be evacuated for 25 minutes, and then the polymerization was stopped at the reflux temperature of toluene for 14 hours. The polymer solution was cooled to room temperature and slowly precipitated into methanol (50 mL). The precipitated solid polymer was eluted with methanol and n-hexane in sequence in a Soxhlet extractor. Finally, it was dissolved in chloroform, precipitated into methanol, filtered, and vacuum-dried for one day ...

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Abstract

The invention discloses a narrow-band-gap n-type polymer acceptor and a preparation method and application thereof. A structural formula of the polymer is shown as a formula I, a copolymerization unit 1 in the formula I is an A-D-A type molecule unit, the D is an aromatic condensed ring unit, the A is an electron deficiency acceptor unit, and a copolymerization unit 2 in the formula I is a conjugation aromatic ring unit. A narrow-band-gap n-type polymer material disclosed by the invention has good material film forming property, higher molar absorption coefficient, higher thermal stability, better charge transfer performance and appropriate electronic energy level, can serve as an electron acceptor material to be matched with a p-type electron donor polymer and can be applied to a full-polymer solar cell device. (The formula I is shown in the description.).

Description

technical field [0001] The invention belongs to the field of polymers, and in particular relates to a narrow bandgap n-type polymer receptor and a preparation method and application thereof. Background technique [0002] The energy problem has increasingly become an urgent problem in the world, and solar energy has the advantages of being clean, green and pollution-free, widely distributed, inexhaustible and inexhaustible, and has the most development prospects. The development and utilization of solar energy will be an effective way to deal with the energy crisis. solution. Since organic conjugated polymers were discovered in 1977 as semiconductor materials, the related research has attracted much attention, and its flexibility, large area, and low-cost preparation have become its outstanding advantages. In the field of narrow-bandgap polymers, narrower-bandgap polymers can be applied to many fields, such as polymer near-infrared light-emitting diodes, polymer solar cells,...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/126C08G2261/51C08G2261/414C08G2261/411C08G2261/592C08G2261/3223C08G2261/3243C08G2261/1412C08G2261/146C08G2261/143C08G2261/124H10K85/151Y02E10/549
Inventor 张志国杨延康李永舫
Owner INST OF CHEM CHINESE ACAD OF SCI
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