An organic electroluminescent device based on a phosphorescent host material
A light-emitting subject and luminescent technology, which is applied in the manufacture of electric solid-state devices, semiconductor devices, semiconductor/solid-state devices, etc., can solve problems such as difficult flow of electrons, unbalanced charge in the light-emitting layer, and reduced device efficiency.
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Embodiment 1
[0071] Synthesis of Compound 19
[0072]
[0073] Synthesis of Intermediate 19-1
[0074] In a one-necked flask, add naphthaleneboronic acid (3.44g, 20mmol), 2,5-dibromonitrobenzene (6.13g, 22mmol), tetrahydrofuran (100ml) and 2M aqueous potassium carbonate (100ml) and tetrakis(triphenylphosphine ) palladium (0.46g, 0.4mmol), under the protection of nitrogen, heated and refluxed for 5 hours, the reaction was completed, cooled, extracted three times with dichloromethane, the organic layer was dried with anhydrous sodium sulfate, and the organic solvent was removed by rotation, and the crude product was subjected to column layer Purified by analysis to obtain 3.33 g of white solid with a yield of 51%. 1 H NMR (400MHz, CDCl 3 ): δ8.23(d, J=1.7Hz, 1H), 7.92(d, J=8.2Hz, 2H), 7.84(d, J=8.2, 1H), 7.51(t, J=8.0, 2H), 7.42(m,2H),7.38(d,J=8.2Hz,1H),7.32(m,1H).
[0075] Synthesis of Intermediate 19-2
[0076] In a one-necked flask, add intermediate 19-1 (3.27g, 10mmol), triphenyl...
Embodiment 2
[0082] Synthesis of Compound 24
[0083]
[0084] In a three-necked flask, add compound 19-3 (0.099g, 0.25mmol), 2-(3-bromophenyl)-1-phenyl-1H-benzimidazole (0.13g, 0.375mmol), potassium tert-butoxide (0.034g, 0.3mmol) and xylene (20ml), under nitrogen protection, add palladium acetate (0.0028g, 0.0125mmol) and phosphorus ligand (0.0088g, 0.025mmol), then heated to reflux for 24 hours, the reaction was complete, The reaction was cooled, the solvent was distilled off under reduced pressure, dissolved in dichloromethane, washed with water, dried over anhydrous sodium sulfate, and the organic solvent was removed by rotation. The crude product was purified by column chromatography to obtain 0.085 g of a white solid with a yield of 51%. 1 H NMR (400MHz, CDCl 3): δ8.85-8.87(d, J=8.4Hz, 1H), 8.71-8.73(d, J=8.4Hz, 1H), 8.18-8.22(m, 2H), 8.02-8.04(d, J=7.6 Hz,1H),7.93-7.97(m,1H),7.88-8.90(d,J=7.6Hz,1H),7.08-7.82(m,22H).
[0085] The proton magnetic spectrum of compound 24 is show...
Embodiment 3
[0087] Synthesis of compound 31
[0088]
[0089] Synthesis of Intermediate 31-1
[0090] In a one-necked flask, add naphthaleneboronic acid (3.44g, 20mmol), 2-bromonitrobenzene (4.42g, 22mmol), tetrahydrofuran (100ml), 2MK 2 CO 3 Aqueous solution (100ml) and tetrakis(triphenylphosphine)palladium (0.46g, 0.4mmol) were heated to reflux for 5 hours under the protection of nitrogen, after the reaction was completed, cooled, extracted three times with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate , the organic solvent was removed by rotation, and the crude product was purified by column chromatography to obtain 3.44 g of a white solid with a yield of 69%. 1 H NMR (400MHz, CDCl 3 ):δ8.08(d,J=8.2Hz,1H),7.91(d,J=8.2Hz,2H),7.71(m,1H),7.61(m,1H),7.55–7.38(m,5H) ,7.35(m,1H).
[0091] Synthesis of Intermediates 31-2, 31-3 and Compound 31-4
[0092] In a three-necked flask, add compound 31-1 (2.49g, 10mmol), and dropwise add liquid bromine (0.5ml,...
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