Organic semiconductor material containing dithienothiophene and thienopyrryldiketone units, and preparation method and application thereof
A thiophenepyrrole diketo and organic semiconductor technology are applied in the preparation of organic semiconductor materials, in the field of organic semiconductor materials containing dithienothiophene and thiophenepyrrole dione units, which can solve problems such as low photoelectric conversion efficiency and improve photoelectric conversion. High efficiency, high yield and good electron delocalization performance
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[0027] The preparation method of the organic semiconductor material containing dithienothiophene and thienopyrrole diketone unit comprises the following steps:
[0028] Step S1: In an oxygen-free environment, the dithienothiophene compound (A 1 ) and n-butyllithium (n-BuLi) are added to the first solvent at a molar ratio of 1:2 to 1:4 at -100°C to -25°C to react for 05. to 5 hours, and then add trimethyltin chloride (Me 3 SnCl, the amount of which is 2 to 4 times the molar weight of the dithienothiophene compound), and the reaction was continued for 24 to 48 hours to obtain the product, namely (3,5-dialkyldithieno[3,2-b;2 ',3'-d]thiophene-2,6-diyl)bis(trimethyltin)(B 1 ); wherein, the first solvent is at least one of tetrahydrofuran, ether, dichloromethane, chloroform or ethyl acetate, R 1 , R 2 same or different as C 1 -C 20 The alkyl group; Its reaction formula is as follows:
[0029]
[0030] Step S2: 5-alkylthiophene[3,4-c]-pyrrole-4,6-dione (A 2 ) and N-bromosu...
Embodiment 1
[0036] Embodiment 1. This embodiment discloses an organic semiconductor material with the following structure:
[0037]
[0038] In the above formula, n=20;
[0039] The preparation steps of the above-mentioned organic semiconductor material are as follows:
[0040] 1. Preparation of 3,5-dimethyldithieno[3,2-b; 2′,3′-d]thiophene-2,6-diyl-bis(trimethyltin):
[0041]
[0042] At -100°C, under the protection of argon, add 20.00mL (2.00M) n-butyllithium solution to 2.24g 3,5-dimethyldithieno[3,2-b;2′,3′ -d] In a reaction flask of thiophene and 100 mL of tetrahydrofuran, after stirring for 1 hour, slowly add 7.81 g of trimethyltin chloride dropwise, return to room temperature, and continue stirring for 48 hours. After the reaction, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, and recrystallized to obtain 3,5-dimethyldithieno[3,2-b;2′,3′-d] Thiophene-2,6-diyl-bis(trimethyltin) product.
[0043...
Embodiment 2
[0056] Embodiment 2. This embodiment discloses an organic semiconductor material with the following structure:
[0057]
[0058] In the above formula, n=42;
[0059] The preparation steps of the above-mentioned organic semiconductor material are as follows:
[0060] 1. Preparation of (3,5-dioctyldithieno[3,2-b; 2′,3′-d]thiophene-2,6-diyl)bis(trimethyltin):
[0061]
[0062] At -78°C under nitrogen, add 20.00mL (1.00M) of n-butyllithium solution to 4.21g of 3,5-dioctyldithieno[3,2-b;2′,3′-d ] in a reaction flask of thiophene and 100 mL of tetrahydrofuran, after stirring for 1 hour, slowly add 3.88 g of trimethyltin chloride dropwise, return to room temperature, and continue stirring for 38 hours. After the reaction, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, and recrystallized to obtain (3,5-dioctyldithieno[3,2-b; 2′,3′-d ]thiophene-2,6-diyl)bis(trimethyltin) product.
[0063] MALDI-TOF...
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