Anthraquinonyl-group-containing polymer and preparation method thereof, and organic solar cell device

[0031] Example 1:

[0032] The anthraquinone group-containing polymer of this embodiment is poly{6,6,12,12-tetra-n-octyl-2,8-diyl-6,12-dihydroindeno[1,2-b :1',2'-e]pyrazine-co-2,6-diyl-1,5-bis(n-octyloxy)anthracene-9,10-dione} (where R1 is n-octyl , R2 is n-octyl group, n=50), its structural formula is as follows:

[0033]

[0034] The preparation steps of the above polymer are as follows:

[0035] The reaction formula is as follows:

[0036]

[0037] Under the protection of argon, 6,6,12,12-tetra-n-octyl-2,8-dipinacol borate-6,12-dihydroindeno[1,2-b:1' ,2'-e)pyrazine (191mg, 0.2mmol), 2,6-dibromo-1,5-bis(n-octyloxy)anthracene-9,10-dione (124mg, 0.2mmol) were added to the container In a flask of 10ml toluene solvent, after fully dissolved, potassium carbonate (2mL, 2mol/L) solution was added to the flask, vacuumed to remove oxygen and filled with argon, and then added bistriphenylphosphine palladium dichloride (5.6mg , 0.008mmol); The flask was heated to 100°C for Suzuki coupling reaction for 48h. Subsequently, the coupling reaction was stopped after cooling, and 50 ml of methanol was added dropwise to the flask for sedimentation; after filtering through a Soxhlet extractor, it was extracted with methanol and n-hexane for 24 hours. Then, it was extracted with chloroform as a solvent until it was colorless. The chloroform solution was collected and spin-dried to obtain a red powder. After the collected powder was dried at 50° C. under vacuum for 24 hours, the P1 product was obtained with a yield of 75%.

[0038] The test result is: Molecular weight (GPC, THF, R.I): M n =78.1kDa,M w /M n =2.2.

[0039] figure 1 Is the ultraviolet-visible absorption spectrum of the anthraquinone group-containing polymer prepared in Example 1; figure 1 It can be seen that the polymer has a relatively large and broad absorption between 300 nm and 700 nm, and the maximum absorption peak is at about 588 nm.

[0040] Example 2:

[0041] The anthraquinone group-containing polymer of this embodiment is poly{6,6,12,12-tetramethyl-2,8-diyl-6,12-dihydroindeno[1,2-b:1 ',2'-e]pyrazine-co-2,6-diyl-1,5-bis(n-eicosyloxy)anthracene-9,10-dione}(P2), (where R1 is Methyl, R2 is n-eicosyl, n=68), its structure is as follows:

[0042]

[0043] The preparation steps of the above polymer are as follows:

[0044] The reaction formula is as follows:

[0045]

[0046] Under the protection of a mixture of nitrogen and argon, 6,6,12,12-tetramethyl-2,8-dipinacol borate-6,12-dihydroindeno[1,2-b:1 ',2'-e)pyrazine (169mg, 0.3mmol), 2,6-dibromo-1,5-bis(n-eicosyloxy)anthracene-9,10-dione (287mg, 0.3mmol) Add 15mL of tetrahydrofuran and 15mL of tetrahydrofuran to a 50mL two-necked flask. After fully dissolving, let a mixture of nitrogen and argon and exhaust the air for about 20 minutes. Then add tetrakistriphenylphosphine palladium (4mg, 0.003mmol) to it, and then dissolve it fully. Add sodium bicarbonate (3mL, 2mol/L) solution. After fully ventilating the mixed gas of nitrogen and argon for about 10 minutes, the two-neck flask was added to 70° C. for Suzuki coupling reaction for 96 hours. Subsequently, after cooling, the coupling reaction was stopped, 40 mL of methanol was added to the two-necked flask for precipitation, filtered through a Soxhlet extractor, and then extracted with methanol and n-hexane for 24 hours. Then it was extracted with chloroform as a solvent until it was colorless. The chloroform solution was collected and spin-dried to obtain a red solid, which was collected and dried at 50° C. under vacuum for 24 h to obtain the P2 product. The yield was 82%.

[0047] The test result is: Molecular weight (GPC, THF, R.I): M n =113.8kDa,M w /M n =2.1.

[0048] Example 3:

[0049] The anthraquinone group-containing polymer of this embodiment is poly{6,6,12,12-tetran-eicosyl-2,8-diyl-6,12-dihydroindeno[1,2- b:1',2'-e] pyrazine-co-2,6-diyl-1,5-dimethoxyanthracene-9,10-dione}(P3), (where R1 is two Decalkyl, R2 is methyl, n=10), its structure is as follows:

[0050]

[0051] The preparation steps of the above polymer are as follows:

[0052] The reaction formula is as follows:

[0053]

[0054] Under the protection of nitrogen, the 6,6,12,12-tetran-eicosyl-2,8-dipinacol borate-6,12-dihydroindeno[1,2-b:1', 2'-e) pyrazine (488mg, 0.3mmol), 2,6-dibromo-1,5-bis(methoxy)anthracene-9,10-dione (141mg, 0.33mmol), palladium acetate (3.5 mg, 0.015mmol) and tris(o-methylphenyl)phosphine (21mg, 0.06mmol) were added to a flask containing 12mL of N,N-dimethylformamide, and potassium carbonate (3mL, 2mol) /L) solution, and then purge the flask with nitrogen gas for about 30 minutes; heat the flask to 130°C for Suzuki coupling reaction for 12 hours. Then, after cooling down, the coupling reaction was stopped, 40 mL methanol was added to the flask for precipitation, filtered through a Soxhlet extractor, and then extracted with methanol and n-hexane for 24 hours; then chloroform was used as a solvent to extract until colorless, and the chloroform solution was collected and rotated. A red powder is obtained by drying. After being collected and dried at 50°C under vacuum for 24 hours, it is a P3 product with a yield of 77%.

[0055] The test result is: Molecular weight (GPC, THF, R.I): M n =21.6kDa,M w /M n = 2.4.