Pyridinopyrazine compound as well as preparation method and application thereof
A compound, pyrazine technology, applied in the field of organic electroluminescent materials, can solve problems affecting device life, stability and practicability, lack of red light TADF materials, and insufficient luminous efficiency
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[0045] The present invention provides the preparation method of pyridopyrazine compound described in the technical scheme, comprising the following steps:
[0046] Under a protective atmosphere, the halogenated pyridodicyanopyrazine, compound II, palladium catalyst and basic reagent are mixed, and a coupling reaction is carried out to obtain a pyridopyrazine compound having a structure shown in formula I;
[0047] The structural formula of the halogenated pyridodicyanopyrazine is Among them, R 3 and R 4 independently hydrogen, bromine or iodine, and R 3 and R 4 not simultaneously hydrogen;
[0048] The structural formula of the compound II is R in the compound II 1 and R 2 Independently include any one of hydrogen, triphenylamine substituents, diphenylamine substituents, carbazole substituents, N-phenylcarbazole substituents, phenoxazine substituents and phenothiazine substituents species, and R 1 and R 2 Not simultaneously hydrogen.
[0049] In the present invent...
Embodiment 1
[0083] (1) Synthesis of diiminosuccinonitrile
[0084]
[0085] Add 50mL of acetonitrile to 10mmol of diaminomaleonitrile, stir to dissolve, add 10mmol of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, stir for 15min, filter, and the obtained liquid The components were concentrated and then dried to constant weight to obtain diiminosuccinonitrile (brown solid, 1.01 g, yield 95%).
[0086] (2) Synthesis of compound 5,8-dibromopyrido[3,4-b]-2,3-dicyanopyrazine (5,8-DBrPPD)
[0087]
[0088] 3.6mmol diiminosuccinonitrile and 3mmol 2,5-dibromo-3,4-diaminopyridine were mixed and added to 20mL trifluoroacetic acid in 3 batches, stirred at room temperature for 8h and then poured into ice water. Filter, wash the obtained solid component with water and purify by silica gel column chromatography (eluent is petroleum ether / dichloromethane volume ratio=1 / 1) to obtain 5,8-dibromopyrido[3,4-b] -2,3-Dicyanopyrazine (pale yellow powder, 2.71 g, yield 80%). Structural Characterization Dat...
Embodiment 2
[0096] 3mmol of 5,8-DBrPPD prepared in Example 1, 6.6mmol of 4-triphenylamine borate, 15mmol of potassium carbonate, 0.1mmol of tetrakis(triphenylphosphine)palladium, 45mL of toluene and 7.5mL of water were added to a three-necked flask, and Protection, oil bath, reaction at 100°C for 12h, pour the obtained reaction liquid into distilled water, extract with dichloromethane, concentrate the obtained organic phase and purify by silica gel column chromatography (eluent is petroleum ether / dichloromethane Chloromethane volume ratio = 1 / 3) to obtain pyridopyrazine compounds (I-1, dark red powder, 1.60 g, yield 80%). Structural Characterization Data: 1 H NMR (400MHz, DMSO-d 6 )δ8.90(s,1H),8.12(d,J=7.2Hz,2H),7.55(d,J=8.2Hz,2H),7.37(d,J=8.4Hz,4H),7.26-7.22( m, 8H), 7.10-7.06 (m, 8H), 7.02-6.98 (m, 8H); the molecular ion mass determined by mass spectrometry is: 667.25 (calculated value: 667.78); theoretical element content (%) C 45 h 29 N 7 : C 80.94, H 4.38, N 14.68; measured elem...
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