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A silane-substituted two-dimensional conjugated polymer and its preparation method and application in photovoltaic devices

A two-dimensional conjugated, polymer technology, used in photovoltaic power generation, electric solid-state devices, semiconductor devices, etc., can solve the problems of poor morphology stability, low efficiency, weak absorption in the visible light region, etc.

Active Publication Date: 2018-08-24
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fullerene derivative acceptors represented by PCBM have many disadvantages, such as weak absorption in the visible light region, difficulty in adjusting the energy level, and poor shape stability. Therefore, in recent years, in order to replace the Fullerene acceptors, synthesized a series of new small molecule and polymer non-fullerene acceptor materials
Although blending with different polymer donor materials to prepare solar cells shows certain photovoltaic properties, the efficiency is still low compared with fullerene systems. Therefore, a class of non-fullerene acceptors has been developed. Matching donor polymer materials become a research hotspot

Method used

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  • A silane-substituted two-dimensional conjugated polymer and its preparation method and application in photovoltaic devices
  • A silane-substituted two-dimensional conjugated polymer and its preparation method and application in photovoltaic devices
  • A silane-substituted two-dimensional conjugated polymer and its preparation method and application in photovoltaic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Example 1, 2,6-bis(trimethyltin group) 4,8-bis((3-n-propyl)silthienyl)benzo[1,2-b:4,5-b']di Synthesis of Thiophene (M1) Compound

[0085]

[0086] According to the reaction equation shown above, under the protection of argon, slowly add n-butyllithium (40 ml, 2.5M / L, Stored in n-hexane), the mixture was kept at -78° for 1 hour and slowly warmed to room temperature. Then, tripropylsilyl chloride (19.2 g, 100 mmol) was added, and the mixture was stirred overnight. The mixture was extracted twice with ether, washed with distilled water and brine. Further purification by silica gel column chromatography using hexane as eluent gave 2-(3-propylsilyl)thiophene (A01) as a colorless liquid.

[0087] The structural confirmation data are as follows: GC-MS: m / z=240, 1 HNMR (400MHz, CDCl 3 ),δ(ppm):7.57-7.56(d,1H),7.22(d,1H),7.16-7.15(t,1H),1.40-1.32(m,6H),0.96-0.92(m,9H), 0.80-0.75(m,6H).

[0088] Add 7.20 g (30.0 mmol) of 2-(3-propylsilyl)thiophene (A01) into a 250 mL tw...

Embodiment 2

[0091] Embodiment 2, formula P 1 Synthesis of the indicated polymers

[0092]

[0093] Carry out according to the above reaction equation, take 0.3mmol each of monomer M1 and M2, dissolve it in a mixed solvent of toluene (8mL) and DMF (2mL), exhaust the air with argon for 5 minutes, and then add catalyst tetrakis (triphenyl Phosphine)palladium(0) (20 mg) was followed by further evacuation of air for 25 minutes, and then the polymerization was stopped after 12 hours at the reflux temperature of toluene. The polymer solution was cooled to room temperature, and slowly precipitated into methanol (50 mL), and the precipitated solid polymer was sequentially eluted with methanol and n-hexane in a Soxhlet extractor. Finally dissolve with chloroform and precipitate into methanol, filter, and vacuum dry for one day to obtain the formula P of black solid powder 1 The polymer shown, the productive rate is 81%, GPC: Mn=23.5K; Mw / Mn=2.0.Anal.Calcd for C 66 h 85 f 2 N 3 S 6 Si 2 (...

Embodiment 3

[0094] Embodiment 3, formula P 2 Synthesis of the indicated polymers

[0095]

[0096] According to the above reaction equation, take 0.3mmol of each monomer M1 and M3, dissolve it in a mixed solvent of toluene (8mL) and DMF (2mL), exhaust the air with argon for 5 minutes, and then add the catalyst tetrakis (triphenyl Phosphine)palladium(0) (20 mg) was followed by further evacuation of air for 25 minutes, and then the polymerization was stopped after 12 hours at the reflux temperature of toluene. The polymer solution was cooled to room temperature, and slowly precipitated into methanol (50 mL), and the precipitated solid polymer was sequentially eluted with methanol and n-hexane in a Soxhlet extractor. Finally dissolve with chloroform and precipitate into methanol, filter, and vacuum dry for one day to obtain the formula P of black solid powder 1 The polymer shown, the productive rate is 65%, GPC: Mn=18.2K; Mw / Mn=1.9.Anal.Calcd for C 51 h 65 FOS 6 Si 2 (%): C, 63.70; ...

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Abstract

The invention discloses a silane-substituted two-dimensional conjugated polymer, its preparation method and application in photovoltaic devices. The structural formula of the two-dimensional conjugated polymer is shown in formula I. In formula I, Ar1 is a conjugated aromatic ring or a condensed ring formed by the conjugated aromatic ring, and the conjugated aromatic ring is thiophene, thiophene, Benzene ring, furan or selenophene; R1, R2 and R3 are all independently selected from any of silyl, H, halogen, alkoxy and alkylthio, and at least one substituent in R1, R2 and R3 is A silyl group; the silyl group is a straight-chain or branched-chain silyl group with 1 to 30 carbon atoms. The invention provides a silane-substituted two-dimensional conjugated polymer, the photoelectric performance of the material has been greatly regulated, it has good charge transport performance and suitable electron energy level, and can be used as an electron donor material Matching with narrow-band n-type small molecule acceptor materials, it is applied to non-fullerene polymer solar cell devices.

Description

technical field [0001] The invention relates to a silane-substituted two-dimensional conjugated polymer, a preparation method thereof and an application in photovoltaic devices. Background technique [0002] Energy issues are increasingly becoming an urgent global issue, and solar energy has the advantages of being clean, green, non-polluting, inexhaustible, and inexhaustible, and has the most development prospects. The development and utilization of solar energy will be an effective solution to the energy crisis . So far, through the optimization of molecular structure, device structure and processing technology, the photoelectric conversion efficiency of organic solar cells based on the blending of polymer donors or organic molecular donors and fullerene acceptors has exceeded 10%. It shows great application prospects of organic solar cells (see Li Yongfang Acc.Chem.Res., 2012, 45(5), 723–73; Li Yongfang et al. "Materials and Devices for Polymer Solar Cells"). However, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C08L65/00H01L51/46
CPCC08G61/123C08G61/124C08G61/125C08G61/126C08L65/00C08G2261/18C08G2261/3244C08G2261/91H10K85/113Y02E10/549
Inventor 张志国宾海军李永舫
Owner INST OF CHEM CHINESE ACAD OF SCI
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