Structure, synthesis and application for carbazole polymer hole transporting materials
A technology of hole transport material and hole transport layer, which is applied in the field of new solar cell materials, can solve the problems of complex synthesis steps, high material cost, and high price, and achieve simple preparation process, good thermal stability, and low price. Effect
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Embodiment 1
[0031] The preparation of embodiment 1 polymer I;
[0032] The synthetic route is as follows:
[0033]
[0034] Synthesis of 3,6-dibromo-9-(4-iodophenyl)-9H-carbazole (compound 1): 3,6-dibromocarbazole (5.0 g, 15 mmol) was added to a 150 mL round bottom flask , 1-fluoro-4-iodobenzene (13.5 g, 60 mmol) and cesium carbonate (20.0 g, 60 mmol). Then add 60mL of N,N'-dimethylamide (DMF), continue to stir at 150°C for 24 hours, then let it stand and cool to room temperature, extract with saturated brine and dichloromethane, dry with anhydrous magnesium sulfate, filter, The organic solvent was removed to obtain a crude product, which was purified by column chromatography using a dichloromethane-petroleum ether solution with a volume ratio of 1:9 as the mobile phase to obtain 4.05 g of the target product as a white solid with a yield of 52%. 1 H NMR (400MHz, CDCl 3 )δ7.94(d, J=8.6Hz, 2H), 7.51(d, J=8.7Hz, 2H), 7.24(dd, J=11.5, 8.7Hz, 6H). 13 C NMR (101MHz, CDCl 3 )δ139.71, 139...
Embodiment 2
[0038] The preparation of embodiment 2 polymer II;
[0039]
[0040] 2, the synthesis of 7-dibromo-9-(4-iodophenyl)-9H-carbazole (compound 2): the synthetic process is similar to that of compound 1, but the raw material is 2,7-dibromocarbazole ( 5.0 g, 15 mmol) to replace 3,6-dibromocarbazole, and the final crude product was dried and purified by column chromatography to obtain 5.06 g of the target product as a yellow solid with a yield of 64%. 1 H NMR (400MHz, CDCl 3 )δ7.95 (dd, J=13.0, 7.9Hz, 4H), 7.41 (d, J=8.3Hz, 2H), 7.27 (d, J=6.7Hz, 4H). 13 C NMR (101MHz, CDCl 3 )δ141.72, 139.81, 139.77, 139.71, 136.44, 136.39, 129.12, 129.04, 124.25, 124.20, 124.11, 122.04, 121.81, 121.76, 120.36, 113.14, 113.04, 93.5 + ] calcd for C 18 h 10 Br 2 IN: 524.82; found: 557.871.
[0041] Synthesis of 2,7-dibromo-9-(bis[4-methoxyphenyl]-aminophenyl)-9H-carbazole (compound 4): the synthesis process is similar to that of compound 3, except that the raw materials are Compound 2 (2.8g...
Embodiment 3
[0044] The preparation of embodiment 3 polymer III;
[0045] The synthetic route is as follows:
[0046]
[0047] For the synthesis of compounds 1, 3, and 5, see Example 1, and for the synthesis of compound 4, see Example 2;
[0048] The synthesis process of polymer II: the synthesis process is similar to the synthesis process of polymer I, except that compound 4 (626 mg, 1 mmol) and compound 6 (722 mg, 1 mmol) are used as raw materials, and the final product is dark green solid. GPC: (Mn=6638, PDI=2.45). 1 H NMR (300MHz, CDCl 3 )δ7.71(s, 4H), 7.56-7.32(m, 6H), 7.21(d, J=30.9Hz, 18H), 6.86(s, 8H), 3.79(d, J=16.9Hz, 12H).
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