Organic electroluminescent device
An electroluminescent device and a luminescent technology, applied in the direction of electric solid-state devices, electrical components, luminescent materials, etc., can solve the problems of reduced device characteristics, low driving voltage luminous efficiency, insufficient electron barrier properties, etc.
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Embodiment 1
[0201]
[0202] 4-{(biphenyl-4-yl)-phenylamino}-4"-{(biphenyl-4-yl)-amino}-3-phenyl-1 was added to the nitrogen-substituted reaction vessel, 1'; 3', 1"-terphenyl 17.0g, bromobenzene 4.12g, palladium acetate 0.13g, tri-tert-butylphosphine 50% (w / v) toluene solution 0.33ml, sodium tert-butoxide 2.73g, 190 ml of toluene was added, heated, and stirred at 80° C. for 3 hours. After cooling, the insoluble matter was removed by filtration, concentrated, and purified by column chromatography (carrier: silica gel, eluent: toluene / n-hexane). The solid precipitated by the addition of acetone was collected to give 4,4"-bis{(biphenyl-4-yl)-phenylamino}-3-phenyl-1,1';3',1"-terphenyl (Compound 1-12) 13.29 g of white powder (yield: 71%).
[0203] The structure of the obtained white powder was identified using NMR.
[0204] use 1 H-NMR (CDCl 3 ) detected the following 44 hydrogen signals.
[0205] δ (ppm) = 7.62-7.58 (4H), 7.55-7.49 (4H), 7.48-7.38 (6H), 7.37-7.05 (30H).
[0206]
Embodiment 2
[0208]
[0209] Add 4,4"-bis{(biphenyl-4-yl)-amino}-3,3"-diphenyl-1,1'; 4',1"-triple 16.3g of benzene, 18.6g of iodobenzene, 0.29g of copper powder, 9.61g of potassium carbonate, 1.85g of 3,5-di-tert-butyl salicylic acid, 0.47g of sodium bisulfite, 20ml of dodecylbenzene and heating , Stir at 190-200°C for 17 hours. Cool, add 1500ml of toluene, 40g of silica gel, and 20g of activated clay, and stir. Remove insoluble matter by filtration, concentrate, and repeatedly recrystallize with chlorobenzene to obtain 4,4" -White powder of bis{(biphenyl-4-yl)-phenylamino}-3,3"-diphenyl-1,1'; 4',1"-terphenyl (compound 1-9) 9.65 g (49% yield).
[0210] The structure of the obtained white powder was identified using NMR.
[0211] use 1 H-NMR (CDCl 3 ) detected the following 48 hydrogen signals.
[0212] δ(ppm)=7.62(4H), 7.52(4H), 7.45(4H), 7.36-7.04(32H), 6.99(4H).
[0213]
Embodiment 3
[0215] Synthesis of
[0216] 16.0 g of 4-bis(biphenyl-4-yl)amino-2,6-diphenyl-bromobenzene, 4-{N-(biphenyl-4-yl)- 10.2 g of N-phenylamino}phenylboronic acid, 0.60 g of tetrakistriphenylphosphine palladium, 4.62 g of potassium carbonate, 60 ml of water, 320 ml of toluene, and 60 ml of ethanol were heated and stirred under reflux for 18 hours. After cooling and adding 200 ml of water, the organic layer was collected by a liquid separation operation. The organic layer was dehydrated using anhydrous magnesium sulfate, adsorbed and purified using 40 g of silica gel, concentrated, and dispersed and washed with methanol to obtain a crude product.
[0217] For the crude product, repeated recrystallization with toluene / ethanol and repeated recrystallization with ethyl acetate gave 4-bis(biphenyl-4-yl)amino-4'-{(biphenyl-4-yl)-benzene 12.7 g (yield: 57%) of white powder of 1-amino}-2,6-diphenyl-biphenyl (compound 1-23).
[0218] The structure of the obtained white powder was identif...
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