Organic molecular material containing diphenyl [b, d] thiophene-5, 5 '-dioxide and application thereof

Abstract

The invention belongs to the technical field of organic functional materials, and relates to a diphenyl [b, d] thiophene-5, 5 '-dioxide-containing organic molecular material (DBTO-MTP) and application thereof, and the molecular material DBTO-MTP can be used as a modification layer of a non-doped hole transport layer and a classical hole transport layer (PTAA) to be applied to a planar perovskite solar cell. According to the planar perovskite solar cell based on the DBTO-MTP as the non-doped hole transport layer, the highest energy conversion efficiency can reach 18.72%. According to the planar perovskite solar cell based on DBTO-MTP modification, the highest energy conversion efficiency can reach 21.19% (the efficiency of a device without a modification layer is 19.02%).

Description

technical field

[0001] The invention belongs to the technical field of organic functional materials, in particular to an organic molecular material containing diphenyl[b,d]thiophene-5,5'-dioxide and an application thereof. 5,5'-dioxide as the central unit, bis(4-methylthio)aniline (DBTO-MTP) is symmetrically connected at both ends, and organic molecular materials are modified as undoped hole transport layer and classical hole transport layer layers are used in perovskite solar cells. Background technique

[0002] In recent years, organic-inorganic perovskite solar cells (PSCs) have developed rapidly. In less than ten years, scientists have continuously explored and studied perovskite solar cells, and the efficiency of this type of cells has exceeded 25% (H .Min,T.J.Shin,S.Seok et al.Perovskite solar cells with atomically coherentinterlayers on SnO 2 electrodes, Nature, 2021, 598, 444-450). In high-performance PSCs, hole transport materials (HTMs) play a key role in the e...

Examples

Embodiment 1

[0022] Embodiment 1, the synthesis of DBTO-MTP

[0023] 50ml of dry toluene was added to the two-necked flask, and dibenzo[b,d]thiophene-5,5'-dioxide (1.122g, 1 equivalent), bis(4-methylthio)-aniline (1.723g) were taken , 2.2 equiv), dipalladium tridibenzylideneacetone (82 mg, 0.03 equiv), tri-tert-butylphosphine tetrafluoroborate (52.2 mg, 0.06 equiv) and sodium tert-butoxide (864 mg, 3 equiv) were added to the flask , 110 degrees reaction 12h. After the solution was cooled, deionized water and dichloromethane were added for extraction, and the organic phase was washed with saturated aqueous sodium chloride solution. Add anhydrous magnesium sulfate to dry, and purify by neutral alumina chromatography column, the eluent is 1:2 (v / v) ethyl acetate / petroleum ether. The obtained product was recrystallized from methanol + acetone, and the product DBTO-MTP was collected as a pale yellow solid (1.09 g, 49.6%). Compounds were characterized by mass spectrometry. C 40 H 34 N 2 O...

Embodiment 2

[0027] Example 2. Photovoltaic properties of inverted perovskite solar cells based on DBTO-MTP as undoped hole transport layer

[0028] CH-based preparation of DBTO-MTP as an undoped hole transport layer 3 NH 3 PbI 3-x Cl x Perovskite solar cell devices. The inverted device structure is ITO / DBTO-MTP / CH 3 NH 3 PbI 3-x Cl x / C 60 / BCP / Ag( image 3 ).

[0029] The preparation method of the inverted device is as follows: ITO glass was washed with detergent, ethanol, and acetone ultrasonically for 15 min successively, dried with dry air, and UVO treated for 20 min. Then spin-coat 10 mg / mL non-doped hole transport material DBTO-MTP chlorobenzene solution at 5000 rpm (30 s), and then anneal at 100 °C for 5 min in a glove box. Spin coating PdI at 3500rpm2 , add CH dropwise after 20s 3 NH 3 I, annealed at 90°C for 8 min after the operation. 20nm C was deposited on the perovskite layer by evaporation method. 60 and 8nm BCP. Finally at 2.0×10 -6 A layer of silver electro...

Embodiment 3

[0031] Example 3. Photovoltaic properties of inverted perovskite solar cells based on DBTO-MTP as hole transport layer modification layer

[0032] CH-based preparation using DBTO-MTP as modified layer 3 NH 3 PbI 3-x Cl x Perovskite solar cell devices. The inverted device structure is ITO / PTAA / DBTO-MTP / CH 3 NH 3 PbI 3-x Cl x / C 60 / BCP / Ag( Figure 5 ).

[0033] The preparation method of the inverted device is as follows: ITO glass was washed with detergent, ethanol, and acetone ultrasonically for 15 min successively, dried with dry air, and UVO treated for 20 min. The hole transport material PTAA was then spin-coated at 5000 rpm (40 s), PTAA was dissolved in 1 ml of chlorobenzene, and then annealed at 100 °C for 5 min in a glove box. Continue to spin-coat different concentrations of DBTO-MTP toluene solutions on PTAA. Spin coating PdI at 3500rpm 2 , add CH dropwise after 20s 3 NH 3 I, annealed at 90°C for 8 min after the operation. 20nm C was deposited on the pe...

technical field

[0001] The invention belongs to the technical field of organic functional materials, in particular to an organic molecular material containing diphenyl[b,d]thiophene-5,5'-dioxide and an application thereof. 5,5'-dioxide as the central unit, bis(4-methylthio)aniline (DBTO-MTP) is symmetrically connected at both ends, and organic molecular materials are modified as undoped hole transport layer and classical hole transport layer layers are used in perovskite solar cells. Background technique

[0002] In recent years, organic-inorganic perovskite solar cells (PSCs) have developed rapidly. In less than ten years, scientists have continuously explored and studied perovskite solar cells, and the efficiency of this type of cells has exceeded 25% (H .Min,T.J.Shin,S.Seok et al.Perovskite solar cells with atomically coherentinterlayers on SnO 2 electrodes, Nature, 2021, 598, 444-450). In high-performance PSCs, hole transport materials (HTMs) play a key role in the e...

Examples

Embodiment 1

[0022] Embodiment 1, the synthesis of DBTO-MTP

[0023] 50ml of dry toluene was added to the two-necked flask, and dibenzo[b,d]thiophene-5,5'-dioxide (1.122g, 1 equivalent), bis(4-methylthio)-aniline (1.723g) were taken , 2.2 equiv), dipalladium tridibenzylideneacetone (82 mg, 0.03 equiv), tri-tert-butylphosphine tetrafluoroborate (52.2 mg, 0.06 equiv) and sodium tert-butoxide (864 mg, 3 equiv) were added to the flask , 110 degrees reaction 12h. After the solution was cooled, deionized water and dichloromethane were added for extraction, and the organic phase was washed with saturated aqueous sodium chloride solution. Add anhydrous magnesium sulfate to dry, and purify by neutral alumina chromatography column, the eluent is 1:2 (v / v) ethyl acetate / petroleum ether. The obtained product was recrystallized from methanol + acetone, and the product DBTO-MTP was collected as a pale yellow solid (1.09 g, 49.6%). Compounds were characterized by mass spectrometry. C 40 H 34 N 2 O...

Embodiment 2

[0027] Example 2. Photovoltaic properties of inverted perovskite solar cells based on DBTO-MTP as undoped hole transport layer

[0028] CH-based preparation of DBTO-MTP as an undoped hole transport layer 3 NH 3 PbI 3-x Cl x Perovskite solar cell devices. The inverted device structure is ITO / DBTO-MTP / CH 3 NH 3 PbI 3-x Cl x / C 60 / BCP / Ag( image 3 ).

[0029] The preparation method of the inverted device is as follows: ITO glass was washed with detergent, ethanol, and acetone ultrasonically for 15 min successively, dried with dry air, and UVO treated for 20 min. Then spin-coat 10 mg / mL non-doped hole transport material DBTO-MTP chlorobenzene solution at 5000 rpm (30 s), and then anneal at 100 °C for 5 min in a glove box. Spin coating PdI at 3500rpm2 , add CH dropwise after 20s 3 NH 3 I, annealed at 90°C for 8 min after the operation. 20nm C was deposited on the perovskite layer by evaporation method. 60 and 8nm BCP. Finally at 2.0×10 -6 A layer of silver electro...

Embodiment 3

[0031] Example 3. Photovoltaic properties of inverted perovskite solar cells based on DBTO-MTP as hole transport layer modification layer

[0032] CH-based preparation using DBTO-MTP as modified layer 3 NH 3 PbI 3-x Cl x Perovskite solar cell devices. The inverted device structure is ITO / PTAA / DBTO-MTP / CH 3 NH 3 PbI 3-x Cl x / C 60 / BCP / Ag( Figure 5 ).

[0033] The preparation method of the inverted device is as follows: ITO glass was washed with detergent, ethanol, and acetone ultrasonically for 15 min successively, dried with dry air, and UVO treated for 20 min. The hole transport material PTAA was then spin-coated at 5000 rpm (40 s), PTAA was dissolved in 1 ml of chlorobenzene, and then annealed at 100 °C for 5 min in a glove box. Continue to spin-coat different concentrations of DBTO-MTP toluene solutions on PTAA. Spin coating PdI at 3500rpm 2 , add CH dropwise after 20s 3 NH 3 I, annealed at 90°C for 8 min after the operation. 20nm C was deposited on the pe...

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