Copolymer containing cyclopentadiene bithiophene-benzo-2 (benzothiadiazole) as well as preparation method and application thereof
A technology of benzothiadiazole and dithiophene, which is applied in semiconductor/solid-state device manufacturing, electric solid-state devices, semiconductor devices, etc., can solve the problem of wide band gap, lower photon absorption rate, low energy conversion efficiency of organic solar cells, etc. question
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[0042] The preparation method of the benzo[2,1-b:3,4-b']dithiophene-benzobis(benzothiadiazole) copolymer of one embodiment, such as figure 1 shown, including the following steps:
[0043] Step S100, providing compound A and compound B.
[0044] A is: B is: Among them, R 1 , R 2 for C 1 ~C 20 the alkyl group, R 3 , R 4 for C 1 ~C 20 Alkyl or C 1 ~C 16 of alkoxy.
[0045] Wherein the preparation of compound A comprises the following steps:
[0046] Step S111, adding 2-amino-5-nitroaniline to thionyl chloride (SOCl 2 ), add pyridine dropwise while stirring (the structural formula is Molecular formula is C 5 h 5 N,), wherein the solid-to-liquid ratio of 2-amino-5-nitroaniline to pyridine is 3mol:40ml, and then heated to 80°C~90°C for reflux reaction for 24 hours, then remove excess thionyl chloride, add after cooling Precipitate with deionized water, collect the solid, wash it and dry it in vacuum to obtain 5-nitro-2,1,3 benzothiadiazole.
[0047] The reactio...
Embodiment 1
[0088] This example discloses poly{4,5-bis(3,7-dimethyl)octylbenzo[2,1-b:3,4-b']dithiophene-6,7-bis with the following structural formula (3,7-Dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (benzo[2,1-b:3,4- b'] Dithiophene-benzobis(benzothiadiazole) copolymer P1):
[0089]
[0090] The preparation process of the above-mentioned benzo[2,1-b:3,4-b']dithiophene-benzobis(benzothiadiazole) copolymer P1 is as follows:
[0091] 1.1. Preparation of compound 5-nitro-2,1,3 benzothiadiazole
[0092]
[0093] Add 2-amino-5-nitroaniline (22.95g, 0.15mol) and 100ml of thionyl chloride into a three-necked flask, stir and slowly add 2ml of pyridine dropwise, heat and reflux at 80~90°C for 24h, stop the reaction , heated to 80°C and rotary evaporated excess SOCl 2 Finally, the reaction product was cooled to room temperature, poured into a large amount of water, stirred, filtered, washed with water and then vacuum-dried to obtain 21.7 g of the product 5-nitro-2,1,3-benzothiad...
Embodiment 2
[0117] This example discloses poly{4,5-di-n-decyloxybenzo[2,1-b:3,4-b']dithiophene-6,7-bis(3,7-dimethyl base) octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)}(benzo[2,1-b:3,4-b']dithiophene-benzene Di(benzothiadiazole) copolymer P2):
[0118]
[0119] The preparation process of above-mentioned benzo[2,1-b:3,4-b']dithiophene-benzobis(benzothiadiazole) copolymer P2 is as follows:
[0120] 2.1, 4,9-dibromo-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole) Prepare with embodiment 1.
[0121] 2.2. Preparation of 4,5-bis(n-decyloxy)-2,7-bis(tributyltinyl)benzo[2,1-b:3,4-b’]dithiophene
[0122]
[0123] Under the protection of nitrogen, add 4,5-bis(n-decyloxy)-2,7-dibromobenzo[2,1-b:3,4-b']dithiophene (6.61g , 0.01mol), add 80ml of tetrahydrofuran solvent, slowly inject n-butyllithium (8.4mL, 2.5M, 0.02mol) with a syringe under the condition of -78℃, continue to stir the reaction for 1h, and use Inject tributyltin chloride (5.6 mL, 0.02 mol) into the syringe...
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