2,7-Alkyl-substituted phenanthrene[9,10-b]pyrazine derivative monomer and its preparation method and polymer
A pyrazine derivative, 10-technology, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problems of difficult monomer synthesis and low polymer performance, and achieve the price of raw materials Low cost, increased molecular weight, high mobility effect
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Embodiment 1
[0033]Example 1: Preparation of 2,7-dioctyl-9,10-phenanthrenequinone
[0034] (1) The preparation of 2,7-dibromo-9,10-phenanthrenequinone is prepared according to the method disclosed in [Polym.Int.2007,56,1507.], and the reaction formula is as follows:
[0035]
[0036] In a 500ml three-neck round bottom flask, add 9,10-phenanthrenequinone (20.8g, 100mmol) and concentrated sulfuric acid (300ml), mechanically stir for 15 minutes, add bromosuccinimide (NBS) (40g, 220mmol ). The reaction was carried out in the dark for 24 hours. After the reaction was completed, the reactant was slowly poured into ice water, filtered with suction, and the filter residue was washed several times with aqueous sodium bicarbonate solution, water and methanol in sequence. After the filter residue was dried, it was recrystallized with N,N-dimethylformamide (DMF) to obtain 22 g of orange solid, yield: 60%. (2) Preparation of 2,7-dibromo-9,10-dihydroxyphenanthrene, according to [Jpn.KokaiTokkyoKoho...
Embodiment 2
[0049] Example 2: Preparation of 10,13-dibromo-2,7-dioctyldibenzo[a,c]phenazine, the reaction formula is as follows:
[0050]
[0051] In a 50 ml three-necked flask, add 2,7-dioctyl-9,10-phenanthrenequinone (4.32g, 10mmol), 3,6-dibromo-1,2-phenylenediamine (2.66g, 10mmol), Acetic acid (20 mL) and tetrahydrofuran (5 mL) were heated and stirred at 60° C. overnight. After the reaction was completed, the reactant was poured into water, filtered, and the filter residue was recrystallized from a mixed solution of ethanol / tetrahydrofuran to obtain 5.9 g of a light yellow solid, with a yield of 90%. 1 HNMR (300MHz, CDCl3) δ (ppm): 9.12 (s2H), 8.33 (d, 2H), 7.97 (s, 2H), 7.58 (d, 2H), 2.89 (t, 4H), 1.83-1.75 (m, 4H), 1.46-1.25(m, 20H), 0.88(t, 6H).
Embodiment 3
[0052] Example 3: Preparation of 10,13-dibromo-2,7-dioctyldibenzo[f,h]pyrido[4,3-b]quinoxaline, the reaction formula is as follows:
[0053]
[0054] In a 50 ml three-necked flask, add 2,7-dioctyl-9,10-phenanthrenequinone (2.16g, 5mmol), 3,4-diamino-2,5-dibromopyridine (1.34g, 5mmol), Acetic acid (20 mL) and tetrahydrofuran (5 mL) were heated and stirred at 60° C. overnight. After the reaction was completed, the reactant was poured into water, filtered, and the filter residue was recrystallized from a mixed solution of ethanol / tetrahydrofuran to obtain 3 g of dark yellow solid, yield: 90%. 1 HNMR (300MHz, CDCl3) δ (ppm): 8.87 (s2H), 8.75 (s, 1H), 8.17 (d, 2H), 7.53 (t, 2H), 2.83 (t, 4H), 1.79-1.74 (m, 4H), 1.41-1.25(m, 20H), 0.89(t, 6H).
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