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Spiro indene-based hole transporting small molecule and applications in perovskite solar cells

A small molecule, spiroindene technology, which is applied in the field of perovskite solar cells, can solve the problems that limit large-scale application, and achieve the effects of easy synthesis and purification, high photoelectric conversion efficiency, and simple synthesis route

Active Publication Date: 2019-06-04
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These issues increase the synthesis cost of Spiro-OMeTAD [12] , which limits its large-scale application

Method used

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  • Spiro indene-based hole transporting small molecule and applications in perovskite solar cells
  • Spiro indene-based hole transporting small molecule and applications in perovskite solar cells
  • Spiro indene-based hole transporting small molecule and applications in perovskite solar cells

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The synthesis of compound A is achieved through two schemes:

[0058] Under argon, 1.14g (1mmol) of compound 6, 1.1g (4.8mmol) of 4,4'-dimethoxydiphenylamine, 0.036g (0.039mmol) of Pd 2 (dba) 3 , 0.032g (0.158mmol) tri-tert-butylphosphine, 0.77g (8mmol) sodium tert-butoxide and 20mL toluene were mixed and stirred, and the temperature was raised to 110°C for 12h. After the reaction, evaporate toluene to dryness, add ethyl acetate and water, extract, separate liquid, dry over anhydrous sodium sulfate, use neutral alumina, n-hexane and ethyl acetate mixed solvent as eluting agent, column separation to obtain Yellow solid 1.00 g (58% yield). LC-MS: C 115 h 102 N 6 o 10 , calculated value: 1726.77, measured value: [M] + = 1726.77. 1 H NMR (400MHz, DMSO) δ7.78(d, J=8.3Hz, 4H), 7.73(d, J=1.6Hz, 4H), 7.63(d, J=8.4Hz, 4H), 7.36(d, J =8.8Hz, 4H), 7.30(s, 2H), 7.11(dd, J=8.9, 1.6Hz, 4H), 6.88(d, J=9.0Hz, 16H), 6.82(d, J=9.0Hz, 16H ), 6.55(s, 2H), 3.70(s, 30H), 2.36(dd, J...

Embodiment 2

[0060] The synthesis of embodiment 2 compound B:

[0061] Under argon condition, 1.14g (1mmol) compound 6, 0.965g (4.4mmol) N-phenyl-1-naphthylamine, 0.036g (0.039mmol) Pd 2 (dba) 3 , 0.032g (0.158mmol) tri-tert-butylphosphine, 0.77g (8mmol) sodium tert-butoxide and 20mL toluene were mixed and stirred, and the temperature was raised to 110°C for 12h. After the reaction, evaporate toluene to dryness, add dichloromethane and water, extract, separate, and dry over anhydrous sodium sulfate, use neutral alumina, use a mixed solvent of n-hexane and ethyl acetate as eluent, and separate 0.98 g of yellow solid was obtained (58% yield). LC-MS: C 123 h 94 N 6 o 2 , calculated value: 1686.74, measured value: [M] + = 1686.74. 1 H NMR (400MHz, DMSO) δ8.18 (s, 4H), 7.94–7.78 (m, 14H), 7.69 (d, J = 7.8Hz, 4H), 7.55 (t, J = 9.7Hz, 8H), 7.46 –7.29(m, 26H), 7.13(d, J=8.0Hz, 6H), 7.06(t, J=7.3Hz, 4H), 7.00(d, J=8.9Hz, 4H), 6.65(s, 2H) , 3.83(s, 6H), 2.45(d, J=19.9Hz, 4H), 1.59–1.45(m, ...

Embodiment 3

[0064] Application of hole transport materials containing spiroindene structure in perovskite solar cell devices.

[0065] A perovskite solar cell device, such as figure 1 As shown, each layer is glass substrate 1, FTO cathode 2, dense TiO 2 Layer 3, perovskite layer 4, hole transport layer 5 and Au electrode 6, the hole transport layer 5 is prepared from the above-mentioned spirocyclic hole transport small molecule material (such as compound A).

[0066] The preparation process of the perovskite solar cell device:

[0067] (1) Cleaning: The FTO glass substrate was ultrasonically cleaned sequentially with isopropanol, ethanol, and secondary water to remove pollutants on the substrate surface, and the cleaned FTO glass substrate was blown dry with nitrogen. Treat with UV-ozone for 20 minutes before use to further remove organic matter on the surface;

[0068] (2) Dense TiO 2 Layer preparation: prepare 0.2mol / L titanium tetrachloride aqueous solution, soak the clean FTO glas...

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Abstract

The invention provides a hole transporting small molecule material containing a spiro indene structure. According to the present invention, the hole transporting small molecule material uses a spiro indene structure as a core, has the similar spiro-atom connection of a classical material Spiro-OMeTAD, and has good solubility; by introducing a carbazole triphenylamine-based dendritic unit, the goodHOMO energy level and the good hole mobility can be ensured; and with the application of the hole transporting small molecule material containing the spiro indene structure as the hole transporting layer in perovskite solar cells, the photoelectric conversion efficiency can be up to 18.55%.

Description

technical field [0001] The invention relates to the field of perovskite solar cells, in particular to a preparation method of a small hole-transporting molecule containing a spiroindene structure and its application in perovskite solar cell devices. Background technique [0002] In recent years, people have paid more and more attention to the "energy crisis" and the environmental problems caused by the combustion of fossil fuels. It is imperative to develop renewable and environmentally friendly new energy sources. Among them, solar energy is very important to the sustainable development of human society because it is "inexhaustible and inexhaustible" and the cleanest. The development of low-cost, high-efficiency new solar cells has become a research hotspot in recent years. Among them, perovskite solar cells have developed rapidly, and the device efficiency has increased from 3.8% in 2009. [1] Rapidly improved to 22.1% in 2016 [2] , has attracted worldwide attention and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88H01L51/42H01L51/46
CPCY02E10/549
Inventor 李灿郭鑫王旭超张静
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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