Triphenylamine-Benzothiophene Organic Small Molecule Hole Transport Materials and Their Applications

Abstract

The invention discloses a triphenylamine-benzothiophene organic small molecule hole transport material and its application. The material has a special heterocyclic-containing conjugated system and a triphenylamine structural unit with an alkyl chain. It has good solubility in solvents and good hydrophobicity, and the large two-dimensional conjugated planar structure can effectively improve hole mobility. Applying it to perovskite solar cells can improve the stability of the device, increase the current density and High photoelectric conversion rate has broad application prospects.

Description

technical field

[0001] The invention relates to a small organic molecule hole transport functional material and its application, in particular to a triphenylamine-benzothiophene organic small molecule hole transport material and its application as an energy conversion material, belonging to the technical field of solar cell materials . Background technique

[0002] As we all know, with the continuous development of the economy, the ecological environment continues to deteriorate, and energy sources are increasingly exhausted. Finding sustainable green new energy sources to change the current severe energy situation has become the most important goal of scientists all over the world. Among the many existing new energy sources, solar energy has attracted widespread attention because of its abundant reserves on the earth, wide irradiation range, and clean and pollution-free advantages. Solar cells designed based on the principle of photovoltaic effect are the most potential an...

Examples

Embodiment 1

[0046] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport material with structural unit of formula II.

[0047] A kind of triphenylamine-benzothiophene organic small molecule hole transport material whose chemical structural formula is II, its synthetic route is as follows:

[0048]

[0049] Synthesis of intermediate (2):

[0050] Add 2.2g of compound 1, 1.4g of zinc powder and 30mL of water into a 100mL three-neck flask, then add 6g of NaOH, and heat the mixture under reflux for 1h. Then, add 5.0g n-hexane bromide and equivalent catalyst tetrabutylammonium bromide (Bu 4 NBr), the reaction was heated to reflux for 6h. The mixture was poured into ice water, extracted twice with 200 mLTHF, the organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and the initial product was recrystallized with absolute ethanol to obtain white crystals with a yield of 80%.

[0051] NMR characterization data...

Embodiment 2

[0074] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport material with chemical structure III.

[0075] A chemical structural formula triphenylamine-benzothiophene organic small molecule hole transport material, the synthesis route is as follows:

[0076]

[0077] Synthesis of intermediate (6):

[0078] Add 10g of 4-iodophenol, 8.9g of isooctane bromide, 19g of potassium carbonate and 150mL of DMF into a 250mL three-neck reaction flask, under nitrogen protection, and stir at reflux for 12h at 120°C. Then the mixture was poured into 1M NaOH aqueous solution, extracted with dichloromethane, the organic liquids were combined, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off by rotary evaporation, and the crude product was separated and purified by column chromatography to obtain a colorless liquid with a yield of 53%.

[0079] NMR characterization data of intermediate (6):

[0080] 1 H NMR (CDCl 3 ,500MHz),...

Embodiment 3

[0102] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport material with chemical structure IV.

[0103] A triphenylamine-benzothiophene organic small molecule hole transport material of chemical structural formula IV, its synthetic route is as follows:

[0104]

[0105] Synthesis of intermediate (10):

[0106] Dissolve 5.7 g of monomer M3 and 2.2 g of compound 9 in 45 mL of toluene, then add 2M K 2 CO 3 (12mL) aqueous solution, nitrogen protection, add 0.1mg catalyst Pd (PPh 3 ) 4 , The reaction was vigorously stirred at 110°C for 24h. The mixture was cooled to room temperature, extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and purified by column chromatography to obtain intermediate 10 with a yield of 64%.

[0107] NMR characterization data of intermediate (10):

[0108] 1 H NMR (400MHz, CDCl 3 ,ppm): δ8.75(s 2H),7.80(d,1H),7.74(d,1H),7.6...

technical field

[0001] The invention relates to a small organic molecule hole transport functional material and its application, in particular to a triphenylamine-benzothiophene organic small molecule hole transport material and its application as an energy conversion material, belonging to the technical field of solar cell materials . Background technique

[0002] As we all know, with the continuous development of the economy, the ecological environment continues to deteriorate, and energy sources are increasingly exhausted. Finding sustainable green new energy sources to change the current severe energy situation has become the most important goal of scientists all over the world. Among the many existing new energy sources, solar energy has attracted widespread attention because of its abundant reserves on the earth, wide irradiation range, and clean and pollution-free advantages. Solar cells designed based on the principle of photovoltaic effect are the most potential an...

Examples

Embodiment 1

[0046] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport material with structural unit of formula II.

[0047] A kind of triphenylamine-benzothiophene organic small molecule hole transport material whose chemical structural formula is II, its synthetic route is as follows:

[0048]

[0049] Synthesis of intermediate (2):

[0050] Add 2.2g of compound 1, 1.4g of zinc powder and 30mL of water into a 100mL three-neck flask, then add 6g of NaOH, and heat the mixture under reflux for 1h. Then, add 5.0g n-hexane bromide and equivalent catalyst tetrabutylammonium bromide (Bu 4 NBr), the reaction was heated to reflux for 6h. The mixture was poured into ice water, extracted twice with 200 mLTHF, the organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and the initial product was recrystallized with absolute ethanol to obtain white crystals with a yield of 80%.

[0051] NMR characterization data...

Embodiment 2

[0074] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport material with chemical structure III.

[0075] A chemical structural formula triphenylamine-benzothiophene organic small molecule hole transport material, the synthesis route is as follows:

[0076]

[0077] Synthesis of intermediate (6):

[0078] Add 10g of 4-iodophenol, 8.9g of isooctane bromide, 19g of potassium carbonate and 150mL of DMF into a 250mL three-neck reaction flask, under nitrogen protection, and stir at reflux for 12h at 120°C. Then the mixture was poured into 1M NaOH aqueous solution, extracted with dichloromethane, the organic liquids were combined, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off by rotary evaporation, and the crude product was separated and purified by column chromatography to obtain a colorless liquid with a yield of 53%.

[0079] NMR characterization data of intermediate (6):

[0080] 1 H NMR (CDCl 3 ,500MHz),...

Embodiment 3

[0102] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport material with chemical structure IV.

[0103] A triphenylamine-benzothiophene organic small molecule hole transport material of chemical structural formula IV, its synthetic route is as follows:

[0104]

[0105] Synthesis of intermediate (10):

[0106] Dissolve 5.7 g of monomer M3 and 2.2 g of compound 9 in 45 mL of toluene, then add 2M K 2 CO 3 (12mL) aqueous solution, nitrogen protection, add 0.1mg catalyst Pd (PPh 3 ) 4 , The reaction was vigorously stirred at 110°C for 24h. The mixture was cooled to room temperature, extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and purified by column chromatography to obtain intermediate 10 with a yield of 64%.

[0107] NMR characterization data of intermediate (10):

[0108] 1 H NMR (400MHz, CDCl 3 ,ppm): δ8.75(s 2H),7.80(d,1H),7.74(d,1H),7.6...

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