Method for preparing luminescence polymer material having main chain containing imidazole structure unit and usage
A technology of light-emitting polymers and structural units, applied in the field of preparation of light-emitting polymer materials, to achieve the effect of improving carrier transport performance
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Embodiment 1
[0025] Preparation of A monomer
[0026] Embodiment 1 monomer 2, the synthesis of 3-bis(4-bromophenyl)-2,2-dioctyl-2 hydrogen-imidazole
[0027]
[0028] In a 100 ml three-necked flask, add 1.01 g (2.73 mmol) of 4,4'-dibromobiphenyl, 0.69 g (2.73 mmol) of 9-heptadecanone, 20 ml of glacial acetic acid and 4.89 g (63.55 mg mol) ammonium acetate forms a mixed solution. The reaction mixture was stirred and refluxed under nitrogen atmosphere for 12 hours, and then cooled to room temperature naturally. Part of the solvent was distilled off under reduced pressure, and then water was added to produce a large amount of precipitate. Filter and wash the precipitate with n-hexane. The obtained primary product was purified by column chromatography (dichloromethane as the eluent) to obtain a white solid with a yield of 68%. 1 H NMR (CDCl 3 , 300MHz, δ / ppm): 7.52-7.22 (m, 8H, Ar-H), 1.95-1.23 (m, 28H, CH 2 ), 0.82(t, 6H, CH 3 ).
Embodiment 2
[0030] Synthesis of monomer 4,5-bis(4-bromophenyl)-2,2-bis(4-hexyloxy)phenyl-2hydro-imidazole
[0031]
[0032] In a 100 ml three-necked flask, add 0.9 g (2.42 mmol) of 4,4'-dibromobibenzoyl, 0.93 g (2.42 mmol) of bis(4-hexyloxy) phenyl ketone, and 30 ml of glacial acetic acid and 4.28 g (55.80 mmol) of ammonium acetate to form a mixed solution. The reaction mixture was stirred and refluxed under nitrogen atmosphere for 24 hours, and then cooled to room temperature naturally. Part of the solvent was distilled off under reduced pressure, and then water was added to produce a large amount of precipitate. Filter and wash the precipitate with n-hexane. The obtained primary product was purified by column chromatography (dichloromethane as eluent) to obtain a white solid with a yield of 38%. 1 H NMR (CDCl 3 , 300MHz, δ / ppm): 7.62-7.32 (m, 16H, Ar-H), 4.04-4.01 (t, 4H, OCH 2 ), 1.62-0.89 (m, 22H, CH 2 and CH 3 ).
[0033] Preparation of B conjugated polymer
Embodiment 3
[0034] Example 3 Synthesis of poly{(9,9-dihexylfluorene)-[2,3-diphenyl-2,2-dioctyl-2 hydrogen-imidazole]} (P1)
[0035]
[0036] Into a 100 ml three-necked flask under nitrogen protection, add 0.502 g (1 mmol) of trimethyl 2,7-diboronate-9,9'-dihexylfluorene, 0.602 g (1 mmol) of 2,3- Bis(4-bromophenyl)-2,2-dioctyl-2hydro-imidazole, 12 mg (0.01 mmol) triphenylphosphopalladium, 5 ml toluene and 5 ml potassium carbonate aqueous solution (2M) form a mixed solution . The reaction mixture was heated to about 90° C. for 60 hours in a nitrogen atmosphere, and then naturally cooled to room temperature. The reaction was also introduced into 200 ml of a mixed solution of methanol and water (volume ratio 10:1), and the fibrous solid was suction-filtered, thereby washing the solid with methanol, water and methanol several times. The obtained solid was repeatedly washed with acetone in a Soxhlet extractor to obtain a light yellow solid, which was dried in vacuum to obtain polymer P1 wi...
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