Silane-substituted two-dimensional conjugated polymer and preparation method thereof, and application of silane-substituted two-dimensional conjugated polymer to photovoltaic device

A two-dimensional conjugated, polymer technology, used in photovoltaic power generation, electric solid-state devices, semiconductor devices, etc., can solve problems such as difficult energy levels, poor morphology stability, and low efficiency.

Active Publication Date: 2016-10-26
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, 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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  • Silane-substituted two-dimensional conjugated polymer and preparation method thereof, and application of silane-substituted two-dimensional conjugated polymer to photovoltaic device
  • Silane-substituted two-dimensional conjugated polymer and preparation method thereof, and application of silane-substituted two-dimensional conjugated polymer to photovoltaic device
  • Silane-substituted two-dimensional conjugated polymer and preparation method thereof, and application of silane-substituted two-dimensional conjugated polymer to photovoltaic device

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] According to the above reaction equation, take 0.3 mmol each of monomers M1 and M2, dissolve it in a mixed solvent of toluene (8 mL) and DMF (2 mL), 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 Shown polymer, yield 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 (%): C, 65.68; H, 7.1...

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 and a preparation method thereof, and application of the silane-substituted two-dimensional conjugated polymer to a photovoltaic device. The two-dimensional conjugated polymer has a structural formula as shown in a formula I. In the formula I, Ar1 is a conjugate aromatic ring or a condensed ring constructed by the conjugate aromatic ring, and the conjugate aromatic ring is thiophene, bithiophene, a phenyl ring, furan or selenophene; and R1, R2 and R3 are independently selected from a group consisting of a silyl group, H, halogen, an alkyloxy group and an alkylthio group, and at least one substituent of R1, R2 and R3 is the silyl group which is a straight-chain or branched-chain silyl group with a carbon atom number of 1 to 30. The silane-substituted two-dimensional conjugated polymer provided by the invention has greatly improved photoelectric properties and good charge transfer performance and an appropriate electronic energy level, and is applicable as an electron donor material for matching with a narrowband N-type micromolecular receptor material to a non-fullerene polymer solar cell device.

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 Applications(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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