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Amide bridged organic polymer hole transport material and synthesis method and application thereof

A technology for hole transport materials and polymers, which is applied in the field of amide bridged organic polymer hole transport materials and their synthesis, and can solve the problems of complex synthesis, high cost, and poor photoelectric conversion efficiency of batteries.

Active Publication Date: 2021-05-11
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Currently available hole-transporting materials for trans-perovskite cells are the commercially available poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA) and Poly(3,4 -ethylenedioxythiophene): poly(styrenesulfonate) (PEDOT:PSS), but the synthesis of PTAA is complicated, the cost is high, and the degree of polymerization cannot be controlled, while PEDOT:PSS itself becomes weakly acidic, which will degrade the perovskite light-absorbing layer, and the energy level is the same as Mismatched perovskite materials lead to poor photoelectric conversion efficiency and short battery life

Method used

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  • Amide bridged organic polymer hole transport material and synthesis method and application thereof
  • Amide bridged organic polymer hole transport material and synthesis method and application thereof
  • Amide bridged organic polymer hole transport material and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1, Preparation of 6,6'-bis(4-(bis(4-(4-methylthiophenyl)amino)phenyl)-2,2'-binaphthylamine Z11:

[0039]

[0040] Dibromobinaphthylamine (1.144g, 2.6mmol) and 4-boronic acid pinacol ester-4', 4'-dimethylthiotriphenylamine (2.8015g, 6.5mmol), added tetrakis (triphenyl Phosphine) palladium (0.601g, 0.52mmol), adding sodium carbonate aqueous solution (2.2048g, 20.8mmol, 20ml) was replaced by nitrogen, condensed and refluxed at 100°C for 3h, the reaction solution was cooled to room temperature, extracted, column chromatography ( Petroleum ether (PE) / ethyl acetate (EA)=2:1, vol%) was purified to obtain 1.15 g of polymer monomers with a yield of 46.37%.

[0041] 1H NMR (400MHz, DMSO) δ8.07 (d, J = 1.1Hz, 2H), 7.89 (d, J = 8.9Hz, 2H), 7.66 (d, J = 8.6Hz, 4H), 7.48 (d, J =8.8Hz, 2H), 7.33(s, 2H), 7.27(d, J=8.7Hz, 8H), 7.06(dd, J=14.2, 8.6Hz, 12H), 6.94(d, J=8.8Hz, 2H ),4.81(s,4H),2.50(s,12H).

[0042] 2. Preparation of polymer

Embodiment 2

[0043] Embodiment 2, the preparation of polymer AI-1

[0044]

[0045] Add terephthalic acid (1.328g, 8.0mmol) into the reaction flask, add excess dry toluene, 1-2 drops of dry N,N-dimethylformamide, inject excess thionyl chloride with a syringe, reflux and stir overnight, spin Dry to obtain pure terephthaloyl chloride. 6,6'-bis(4-(bis(4-(4-methoxyphenyl)amino)phenyl)-2,2'-binaphthylamine (1.4 g, 1.57 mmol) was dissolved in excess tetrahydrofuran , inject triethylamine (0.4757g, 1.57mmol) with a syringe, add the terephthaloyl chloride (0.3187g, 1.57mmol) that makes, react 3 days under room temperature. Spin dry reaction solution, add clean rotor, use benign The solvent was dissolved, and then a poor solvent was added to precipitate a solid, filtered with suction, and the filter cake was taken and dried to obtain 1.3 g of the target polymer, with a yield of 76%.

Embodiment 3

[0046] Embodiment 3, the preparation of polymer AI-2

[0047]

[0048] Add 2,3,5,6-tetrafluoroterephthalic acid (1.9g, 8.0mmol) into the reaction flask, add excess dry toluene, 1-2 drops of dry N,N-dimethylformamide, inject excess Thionyl chloride was stirred under reflux overnight, and spin-dried to obtain pure 2,3,5,6-tetrafluoroterephthaloyl chloride. 6,6'-bis(4-(bis(4-(4-methoxyphenyl)amino)phenyl)-2,2'-binaphthylamine (1.4 g, 1.57 mmol) was dissolved in excess tetrahydrofuran , injected triethylamine (0.4757g, 1.57mmol) with a syringe, added the prepared 2,3,5,6-tetrafluoroterephthaloyl chloride (0.4308g, 1.57mmol), and reacted for 3 days at room temperature. Dry the reaction solution, add a clean rotor, dissolve with a good solvent, then add a poor solvent to precipitate a solid, filter with suction, take the filter cake and dry to obtain 1.5 g of the target polymer, with a yield of 82%.

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Abstract

The invention relates to an amide bridged organic polymer hole transport material and a synthesis method and application thereof. According to the design concept, a triarylamine group rich in electrons is used as an electron donating group, so that the conductivity is improved; and the binaphthalene ring structure is favorable for improving pi-pi accumulation among molecules, and meanwhile, the C2 symmetry axis of the binaphthalene ring enables the molecules to have a certain rotation angle, so that molecular aggregation is favorably inhibited. Experimental results prove that the amide bridged organic polymer hole transport material has very high hole mobility and thermal stability. In addition, the dissolvability of the molecule is improved by the non-conjugated structure of the amide group of the molecular skeleton. The designed amide bridged organic polymer molecule has a structure as shown in a formula (AI) defined in the description. The polymer has simple synthesis steps, no catalyst is added in the polymerization process, and the yield is high. The material has relatively high hydrophobicity, thermal stability, film-forming property and ductility, shows good photoelectric property and device stability when being applied to a perovskite solar cell as a hole transport material, and has a wide research prospect.

Description

technical field [0001] The invention belongs to the research field of perovskite solar cells, and relates to an amide-bridged organic polymer hole transport material and its synthesis method and application. Background technique [0002] As an emerging generation of batteries, perovskite solar cells have great research potential. By using metal halide semiconductors as light-absorbing layers and applying them to solar cells, perovskite materials have high light absorption coefficients, adjustable band gaps, and discovery of Considerable progress has been made so far. Inverted structure perovskite solar cells have simple preparation process and low temperature operation, and are expected to be applied to the preparation of rollable, wearable, stacked photovoltaic devices. In the reverse perovskite solar cell structure, the hole transport layer is sandwiched between the ITO glass and the perovskite layer for the separation and transport of carriers. In addition, the film qua...

Claims

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Application Information

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IPC IPC(8): C08G69/32C08G69/28C08G69/42H01L51/42
CPCC08G69/32C08G69/28C08G69/42H10K85/151H10K30/10Y02E10/549
Inventor 薛松罗明宗雪平赵梅华梦楠
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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