Red organic electroluminescent materials and method for preparing same
A luminescent and electromechanical technology, applied in the field of red luminescent materials and their preparation, can solve problems such as difficulties in large-scale production and application, shifting of luminescent wavelengths, cumbersome preparation methods, etc., to reduce self-quenching phenomenon, simple method, and good loading The effect of the streamer transport properties
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Embodiment 1
[0034] Example 1 Preparation of TPA-2CN: Add 2.58g (18mmol) isophorone and 1.19g (18mmol) malononitrile in a 25ml eggplant-shaped bottle, dissolve 0.3g glacial acetic acid and 0.2g acetic anhydride in 10ml DMF, Take 1.3ml into the reaction bottle, dissolve 1.5g of piperidine in 10ml of DMF, take 1.4ml into the reaction bottle. Stir at room temperature for 1 hour and then raise the temperature to 80°C and stir for 1 hour, add 3.55g (13mmol) of 4-diphenylaminobenzaldehyde, continue stirring for 1 hour, pour it into 100ml (containing 3ml concentrated HCl) hot water while hot, and collect The precipitated solid, the crude product was stirred in 15ml of isopropanol and 2ml of water, the solid was collected by suction filtration, and purified by column chromatography (eluent: toluene / petroleum ether (60-90°C)=2 / 1) to obtain a dark purple product 2.27 g, yield 39.8%. Melting point: 187°C; glass transition temperature (Tg): 79°C.
[0035] IR (KBr, cm -1 ): 3033, 2957, 2216, 1590, 1...
Embodiment 2
[0039] Example 2 Preparation of TPA-4CN: 1.36 g (10 mmol) of isophorone and 0.53 g (8.0 mmol) of malononitrile were added to a 25 ml eggplant-shaped bottle. Dissolve 0.24g of glacial acetic acid and 0.16g of acetic anhydride in 10ml of DMF, take 1ml into the reaction flask, dissolve 1.2g of piperidine in 10ml of DMF, take 1ml into the reaction flask. Stir at room temperature for 1 hour, then raise the temperature to 80°C and stir for 1 hour, add 0.90 g (3.0 mmol) of phenyl bis(4-formylphenyl)amine, continue stirring for 1 hour, pour 100 ml (containing 3 ml concentrated HCl) in hot water, collect the precipitated solid, stir the crude product in 15ml of isopropanol and 2ml of water, collect the solid by suction filtration, and purify by column chromatography (eluent: toluene:ethyl acetate=100:1) to obtain dark red Product 0.54 g (28% yield).
[0040] IR (KBr, cm -1 ): 3033, 2957, 2928, 2869, 2217, 1591, 1557, 1521, 1502, 1326, 1289, 1177, 1155, 961, 697.
[0041] 1 H NMR (5...
Embodiment 3
[0046] Example 3 Preparation of TPA-6CN: Add 1.10 g (8.0 mmol) of isophorone and 0.53 g (8.0 mmol) of malononitrile into a 10 ml eggplant-shaped bottle. Dissolve 0.24g of glacial acetic acid and 0.16g of acetic anhydride in 10ml of DMF, take 1ml into the reaction flask, dissolve 1.2g of piperidine in 10ml of DMF, take 1ml into the reaction flask, stir at room temperature for 1 hour, then raise the temperature to 80°C and stir for 1 hour Finally, add 0.49g (1.5mmol) tris (4-formylphenyl) amine, continue to stir for 2 hours, pour into 100ml (containing 3ml concentrated HCl) hot water while hot, collect the precipitated solid, wash with water, column chromatography Purification (eluent: toluene:ethyl acetate=100:3) gave 0.27 g of a dark purple product (yield 23%).
[0047] IR (KBr, cm -1 ): 3033, 2961, 2930, 2869, 2218, 1594, 1557, 1523, 1503, 1324, 1309, 1288, 1177, 1155, 961.
[0048] 1 H NMR (500MHz, CDCl 3 ): δ7.44(d, J=8.7Hz, 6H), 7.12(d, J=8.6Hz, 6H), 7.02(d, J=16Hz, 3H...
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