Polycyclic aromatic hydrocarbon derivative containing naphthyridine group and application of polycyclic aromatic hydrocarbon derivative
A technology containing naphthyridine groups and fused-ring aromatics, which is applied in electrical components, circuits, organic chemistry, etc., can solve the problems of increasing the complexity and disadvantages of the device manufacturing process, reducing the cost of OLEDs, etc., achieving good electron acceptance and reducing The effect of operating voltage and improving luminous efficiency
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[0064] Example 1 Synthesis of various intermediates of 3-bromo-7-aryl-1,5-naphthyridine derivatives
[0065] Synthesis of 1,3-bromo-7-phenyl-1,5-naphthyridine
[0066]
[0067] 1000 ml three-necked flask, equipped with magnetic stirring, nitrogen protection, add 5.72g of 3,7-dibromo-1,5-naphthyridine (molecular weight 286, 0.02mol), phenylboronic acid 2.7g (molecular weight 122, 0.022mol), tetra ( (Triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 2M sodium carbonate aqueous solution 80ml, toluene 80ml, ethanol 80ml. After argon replacement, reflux at 80°C and use thin layer chromatography (TLC) method The reaction was monitored. After 4 hours, TLC found that the reaction of the dibromo compound of the raw material was complete, with only the product point of the monobromide. The temperature was lowered to 25°C, the organic layer was separated, evaporated to dryness, separated by column chromatography, and eluted with ethyl acetate / petroleum ether to obtain 5.7...
Example Embodiment
[0074] Example 2
[0075] Synthesis of compound represented by formula (14)
[0076]
[0077] 1000ml bottle with magnetic stirring, add 5.68g 3-bromo-7-phenyl-1,5-naphthyridine (molecular weight 284, 0.02mol), 9,10-bis(naphthalene-2-yl)anthracene-2 -Boric acid 11.0g (molecular weight 474, 0.022mol), tetrakis ((triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 2M sodium carbonate aqueous solution 80ml, toluene 80ml, ethanol 80ml. After argon replacement, Reflux at 80°C and monitor the reaction by thin layer chromatography (TLC). After 3.5 hours, TLC found that the bromine compound of the raw material had reacted completely, with only product spots. Cool down, separate the organic layer, evaporate to dryness, and separate by column chromatography. After rinsing with petroleum ether, 11.33g of the compound represented by formula (14) was obtained, with a molecular weight of 634 and a yield of 89.3%.
[0078] Product MS (m / e): 634, elemental analysis (C 48 H 30 N 2...
Example Embodiment
[0079] Example 3
[0080] Synthesis of compound represented by formula (15)
[0081] The synthesis procedure is the same as in Example 2, except that 3-bromo-7-phenyl-1,5-naphthyridine is changed to 3-bromo-7-(naphth-1-yl)-1,5-naphthyridine, other reagents Without changing, the compound represented by formula (15) is obtained.
[0082] Product MS (m / e): 684, elemental analysis (C 52 H 32 N 2 ): Theoretical value C: 91.20%, H: 4.71%, N: 4.09%; measured value C: 91.23%, H: 4.73%, N: 4.04%, its nuclear magnetic spectrum ( 1 HNMR) see figure 1 Shown.
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