Hole transport material taking carbazole as core and thiophenazine or phenoxazine as end group, and synthesis method and application thereof
A technology of hole transport material and synthesis method, applied in the field of synthesis of carbazole-based hole transport materials, can solve the problems affecting the commercial application of perovskite solar cells, complex synthesis, difficult purification, etc., and achieve good hole transport The effect of good performance, stability and low price
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Embodiment 1
[0084] Example 1: Synthesis of 3-bromo-10-(4-methoxyphenyl)-10H-phenothiazine (intermediate 1)
[0085] The synthetic route of intermediate 1 is as follows:
[0086]
[0087] Its synthesis method is as follows:
[0088] (1) Add phenothiazine (1.2g, 6mmol), 1-bromo-4-methoxybenzene (1.23g, 6.6mmol), Pd 2 dba 3 (27mg, 0.03mmol), t-Bu 3 PHBF 4 (35mg, 0.12mmol, tri-tert-butylphosphine tetrafluoroborate), sodium tert-butoxide (900mg, 6mmol) and anhydrous toluene (10mL, PhMe), and then carry out three pumping and ventilation, under nitrogen atmosphere at 110 ℃ React for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography (petroleum ether: ethyl acetate = 25:1 as eluent) to obtain a white solid 10-(4-methyl oxyphenyl)-10H-phenothiazine (1.36 g, 74%).
[0089] (2) At 0-5°C, a solution of N-bromosuccinimide (534mg, 3m...
Embodiment 2
[0090] Example 2: Synthesis of 3-bromo-10-(4-methoxyphenyl)-10H-phenoxazine (intermediate 2)
[0091] The synthetic route of intermediate 2 is as follows:
[0092]
[0093] Its synthesis method is as follows:
[0094] (1) Add phenoxazine (1.1g, 6mmol), 1-bromo-4-methoxybenzene (1.23g, 6.6mmol), Pd to a 50mL Schlenk reaction tube 2 dba 3 (27mg, 0.03mmol), t-Bu 3 PHBF 4 (35mg, 0.12mmol, tri-tert-butylphosphine tetrafluoroborate), sodium tert-butoxide (900mg, 6mmol) and anhydrous toluene (10mL, PhMe), and then carry out three pumping and ventilation, under nitrogen atmosphere at 110 ℃ React for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography (petroleum ether: ethyl acetate = 25:1 as eluent) to obtain a white solid 10-(4-methyl Oxyphenyl)-10H-phenoxazine (1.39 g, 80% yield).
[0095](2) Slowly add N-bromosucc...
Embodiment 3
[0097] Synthesis and characterization of embodiment 3TM-5
[0098] Its synthesis method is as follows:
[0099] (1) Add the compound 3,6-dibromo-9-(2-(2-ethoxyethoxy)ethyl)-9Hcarbazole (1.32g, 3mmol) to a 50mL Schlenk reaction tube, diboronic acid Nasolate (2.28g, 9mmol), Pd(dppf)Cl 2 (42mg, 0.06mmol), potassium acetate (1.8g, 18mmol) and anhydrous 1,4-dioxane (15mL), and then perform three pumping and ventilation, and react at 90°C for 16 hours under a nitrogen atmosphere. After completion, the reaction solution was cooled to room temperature, then 50 mL of water was added to the reaction solution, and the aqueous phase was extracted three times with dichloromethane, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the solvent was removed by distillation under reduced pressure, and the crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1 as eluent) to obtain a white solid 9-(2-(2-ethoxyethyl Oxy)ethyl)-3,6-bis(4,4,...
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