Polymeric compound and polymeric electroluminescence element using the same
A technology for polymer compounds and light-emitting elements, applied in the field of polymer light-emitting elements, can solve the problems that the element characteristics such as luminous efficiency are not necessarily sufficient, and the heat resistance and fluorescence intensity of polymer compounds are not necessarily sufficient.
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Synthetic example 1
[0337] [Synthesis of compound (J1)]
[0338] Under an inert gas atmosphere, add 9,10-dibromoanthracene 37.6g (0.11mol), N-(4-tert-butylphenyl) aniline 50.4g (0.22mol), sodium tert-butoxide 25.8g ( 0.27mol), [tris(dibenzylideneacetone)]dipalladium 2.1g (2.2mmol), tri-tert-butylphosphine 1.8g (9mmol), dehydrated toluene 91mL, and stirred at 100°C. Then, the reaction solution was cooled to room temperature, 6.2 g of 1N aqueous hydrochloric acid solution and 1250 mL of methanol were added with stirring, and the precipitated crystals were filtered, washed with MeOH and distilled water, and dried under reduced pressure to obtain a crude product. The crude product was recrystallized from hexane to obtain 61 g of the target compound (J1) (yield 100%, HPLC area percentage 99.3%).
[0339] 1 H-NMR (299.4MHz, CDCl3): 1.27(s, 18H), 6.86(m, 2H), 7.08(m, 8H), 7.20(m, 8H), 7.36(m, 4H), 8.21(m, 4H )
[0340] LC-MS (APPI-MS (posi)): 625 [M+H] +
[0341]
[0342] [Synthesis of compound...
Synthetic example 2
[0348] [Synthesis of compound (J3)]
[0349] Under an inert gas atmosphere, add 15.0 g (44.6 mmol) of 9,10-dibromoanthracene, 16.4 g (89.2 mmol) of N-(4-methylphenyl) aniline, and 10.3 g (107.0 mmol) of sodium tert-butoxide to a three-necked flask. mmol), [tris(dibenzylideneacetone)]dipalladium 0.82g (0.89mmol), tri-tert-butylphosphine 0.75g (3.57mmol), dehydrated toluene 100mL, stirred at 100°C for 5 hours. Then, the reaction solution was cooled to room temperature, neutralized with 1N hydrochloric acid aqueous solution, and 500 mL of methanol was added while stirring, the precipitated crystals were filtered, washed with MeOH and distilled water, and dried under reduced pressure to obtain 22.7 g of the target compound (J3) (yield 93%) , HPLC area percentage 98.5%).
[0350] 1 H-NMR (299.4MHz, CDCl3): 2.26(s, 6H), 6.86(m, 2H), 7.03(m, 12H), 7.17(m, 4H), 7.34(m, 4H), 8.18(m, 4H )
[0351] LC-MS (APPI-MS (posi)): 541 [M+H] +
[0352]
[0353] [Synthesis of compound (J4)...
Synthetic example 3
[0359] [Synthesis of 2,6-di-tert-butylanthracene]
[0360] 153 g of anthracene, 191 g of tert-butanol, and 860 mL of trifluoroacetic acid were stirred at 80-84°C for 24 hours, then cooled to 4°C, filtered, washed with toluene, and washed with hexane to obtain a gray solid. This solid was recrystallized from toluene to obtain 76.2 g of the target 2,6-di-tert-butylanthracene (30.5% yield, 99.1% HPLC area percentage).
[0361] [Synthesis of 9,10-dibromo-2,6-di-tert-butylanthracene]
[0362] To a solution consisting of 76.2 g of 2,6-di-tert-butylanthracene and 2.4 L of carbon tetrachloride, add dropwise a solution consisting of 82.5 g of bromine and 240 mL of carbon tetrachloride at 24 to 30°C within 1 hour. The solution was stirred for another 3 hours. Then, in an ice bath, 1 L of a 10% aqueous sodium hydroxide solution was added dropwise over 1.5 hours, and the aqueous layer was separated from the organic layer. The obtained organic layer was washed with water, carbon tetrach...
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