Novel diketopyrrolopyrrole polymers
A polymer, alkyl technology, applied in diketopyrrolopyrrole dyes, photovoltaic power generation, electrical components and other directions, can solve the problem of not giving DPP-polymer teaching, etc., to achieve excellent solubility, low on-state voltage, excellent The effect of film-forming properties
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Embodiment 1
[0322]
[0323] 0.010 g (0.04 mmol) of palladium(II) acetate and 0.067 g (0.22 mmol) of tris(o-tolyl)phosphine in 10 ml of N-methyl-2-pyrrolidone (NMP) were added to 0.143 g (1.10 mmol) 1,4-divinylbenzene and 0.520g (1.10mmol) 1,4-dioxo-2,5-di-n-hexyl-3,6-bis(bromophenyl)pyrrolo[3,4- c] Pyrrole (prepared according to the method described in EP-A-1087005, EP-A-1087006, or EP-A-133156) was neutralized and stirred at room temperature for 30 minutes. After addition of 0.4 ml (2.89 mmol) triethylamine the reaction mixture was heated at 100°C for 24 hours. The suspension was slurried in 100 ml methanol. The precipitate was filtered off and washed with methanol (3 x 100ml). Low molecular weight impurities can be isolated from the crude polymer by Skoslet extraction in methanol.
[0324] Yield: 0.439g
[0325] Mw: 41000
[0326] in CHCl 3 UV / Vis-absorption in: 499nm
[0327] in CHCl 3 Fluorescence in: 565nm
Embodiment 2
[0329]
[0330] 0.024 g (0.11 mmol) of palladium(II) acetate and 0.165 g (0.54 mmol) of tris(o-tolyl)phosphine in 20 ml of dimethylformamide (DMF) were added under nitrogen atmosphere to 0.353 g (2.71 mmol) of 1 , 4-divinylbenzene and 1.666g (2.71mmol) 1,4-dioxo-2,5-di-n-hexyl-3,6-bis(bromophenyl)pyrrolo[3,4-c]pyrrole Neutralize and stir at room temperature for 30 minutes. After addition of 0.9 ml (6.78 mmol) triethylamine the reaction mixture was heated at 100° C. for 42 hours. After removing 10 ml of DMF in vacuo, the formed polymer was precipitated by adding 200 ml of methanol. The precipitate was dissolved in 110 ml of chloroform and added dropwise to 800 ml of methanol. The precipitated polymer was filtered off and dried under high vacuum.
[0331] Yield: 1.322g
[0332] Mw: 31000
[0333] in CHCl 3 UV / Vis-absorption in: 529nm
[0334] in CHCl 3 Fluorescence in: 579nm
Embodiment 3
[0336]
[0337] 0.230g (0.37mmol) 1,4-dioxo-2,5-di-n-hexyl-3,6-bis(bromophenyl)pyrrolo[3,4-c]pyrrole, 0.003g(0.02mmol) A solution of palladium(II) acetate, 0.1 ml (0.93 mmol) triethylamine and 0.023 g (0.08 mmol) tris(o-tolyl)phosphine in 15 ml NMP was added over 90 minutes under nitrogen atmosphere and under vigorous stirring in 5 ml In 0.487 g (3.74 mmol) 1,4-divinylbenzene in NMP. Then, the reaction mixture was stirred at room temperature for 14 hours and at 80° C. for 6 hours. 100 ml of methanol was added to the resulting mixture. The precipitate formed (product b) was filtered off and washed with 150 ml of methanol. The low molecular weight product a precipitated in the methanol wash solution after 24 hours.
[0338] Yield: 0.075g (product a); Mw: 860
[0339] 0.076g (product b); Mw: 1300
[0340] in CHCl 3 UV / Vis absorption in: 510nm (product a)
[0341] 515nm (product b)
[0342] in CHCl 3 Fluorescence in: 569nm (product a)
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