A spiroindenoid hole-transporting small molecule and its application in perovskite solar cells

A technology for solar cells and hole transport, which is applied in circuits, photovoltaic power generation, electrical components, etc., can solve problems that limit large-scale applications, and achieve the effects of easy synthesis and purification, mild reaction conditions, and increased solubility

Active Publication Date: 2022-06-07
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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  • A spiroindenoid hole-transporting small molecule and its application in perovskite solar cells
  • A spiroindenoid hole-transporting small molecule and its application in perovskite solar cells
  • A spiroindenoid hole-transporting small molecule and its application in perovskite solar cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The synthesis of compound A was achieved by two schemes:

[0058] Under argon, 1.14 g (1 mmol) of compound 6, 1.1 g (4.8 mmol) of 4,4'-dimethoxydiphenylamine, 0.036 g (0.039 mmol) of Pd 2 (dba) 3 , 0.032 g (0.158 mmol) of tri-tert-butylphosphine, 0.77 g (8 mmol) of sodium tert-butoxide and 20 mL of toluene were mixed and stirred, and the temperature was raised to 110° C. to react for 12 h. After the reaction was completed, toluene was evaporated to dryness, ethyl acetate and water were added, and after extraction, liquid separation, and drying over anhydrous sodium sulfate, neutral alumina was used, and a mixed solvent of n-hexane and ethyl acetate was used as the eluent, and the column was separated to obtain 1.00 g of yellow solid (yield 58%). 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...

Embodiment 2

[0060] Synthesis of Example 2 Compound B:

[0061] Under argon, 1.14 g (1 mmol) of compound 6, 0.965 g (4.4 mmol) of N-phenyl-1-naphthylamine, 0.036 g (0.039 mmol) of Pd 2 (dba) 3 , 0.032 g (0.158 mmol) of tri-tert-butylphosphine, 0.77 g (8 mmol) of sodium tert-butoxide and 20 mL of toluene were mixed and stirred, and the temperature was raised to 110° C. to react for 12 h. After the reaction, toluene was evaporated to dryness, dichloromethane and water were added, and after extraction, liquid separation, and drying over anhydrous sodium sulfate, neutral alumina was used, and a mixed solvent of n-hexane and ethyl acetate was used as the eluent, and the column was separated. 0.98 g of yellow solid was obtained (yield 58%). LC-MS: C 123 H 94 N 6 O 2 , Calculated value: 1686.74, Measured value: [M] + = 1686.74. 1 H NMR (400MHz, DMSO) δ 8.18 (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...

Embodiment 3

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

[0065] A perovskite solar cell device such as figure 1 shown, the layers are 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 spiro ring hole transport small molecule material (eg compound A) as described above.

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

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

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

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Abstract

The invention provides a hole-transporting small molecule material containing a spiroindene structure. With the spiroindene structure as the core, it not only has the spiro-atom connection similar to the classic material Spiro-OMeTAD, but also has better solubility; the introduction of carbazole triphenylamine dendritic units can ensure better HOMO energy levels and holes mobility. Used as a hole transport layer in perovskite solar cells, the photoelectric conversion efficiency can reach up to 18.55%.

Description

technical field [0001] The invention relates to the field of perovskite solar cells, in particular to a method for preparing a class of hole-transporting small molecules containing a spiroindene structure and its application in perovskite solar cell devices. Background technique [0002] In recent years, the "energy crisis" and the environmental problems caused by the burning of fossil energy have attracted more and more attention, and it is imperative to develop renewable and environmentally friendly new energy. 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 new low-cost, high-efficiency 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 increased to 22.1% in 2016 [2] , has attracted worldwide attention and h...

Claims

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Application Information

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Patent Type & Authority Patents(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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