Oxadiazole-containing organic semiconductor material and its preparation method and organic electroluminescent device
An organic semiconductor and oxadiazole technology, which is applied in the field of organic semiconductor materials, can solve the problems of high mobility and lack of high thermal stability blue light materials, and achieve the effects of easy production and promotion, easy control of the production process, and simple process
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[0030] The preparation method of the above-mentioned organic semiconductor material containing oxadiazole, the steps are as follows:
[0031] S1, provide the following compounds:
[0032] Compound I: Compound II: Ar-Br; Wherein,
[0033] In the compound formula II, Ar- is an aromatic group, and the aromatic group is preferably the following group:
[0034]
[0035] S2. In an inert gas atmosphere (including nitrogen or argon, etc.), dissolve compounds I and II in an organic solvent containing a catalyst and an alkali solution at a molar ratio of 1:1 to 1:2, and heat to reflux at 70 to 120°C Carry out the Suzuki reaction under the condition for 20~48h, the obtained structural formula is The compound of BOXPAr;
[0036] The reaction formula is as follows:
[0037]
[0038] Wherein, in step S2 of the above-mentioned preparation method, the catalyst is organopalladium (such as tetrakis(triphenylphosphine)palladium, tris(dibenzylideneacetone)dipalladium or bis(triphenyl...
Embodiment 1
[0049] This embodiment discloses an oxadiazole-containing organic semiconductor material with the following structural formula, that is, 5-(4-(anthracene-9-yl)phenyl)-3-tert-butyl-1,2,4-oxadiazole (BOXPA )
[0050]
[0051] Preparation of 5-(4-(anthracen-9-yl)phenyl)-3-tert-butyl-1,2,4-oxadiazole (BOXPA):
[0052]
[0053] Add 4.0mmol of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylboronic acid, 4mmol of 9-bromoanthracene, and 0.012mmol of tetrakis(triphenylphosphine)palladium into the reaction flask , after evacuating and circulating nitrogen for 3 times, the reaction system was in an anaerobic state. Under the protection of nitrogen, 60 mL of tetrahydrofuran and 2 mol / L of Na 2 CO 3 Aqueous solution 40ml, the mixture was heated to 70 ° C reflux reaction for 48h.
[0054]After the reaction, the reaction solution was poured into saturated ammonium chloride aqueous solution, extracted three times with dichloromethane, the organic phase was washed with sodium chloride aqu...
Embodiment 2
[0057] This embodiment discloses an oxadiazole-containing organic semiconductor material with the following structural formula, namely 3-tert-butyl-5-(4-(naphthalene-1-yl)phenyl)-1,2,4-oxadiazole ( BOXPN)
[0058]
[0059] Preparation of 3-tert-butyl-5-(4-(naphthalen-1-yl)phenyl)-1,2,4-oxadiazole (BOXPN):
[0060]
[0061] Add 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylboronate 4mmol, 1-bromonaphthalene 4.5mmol, tetrakis(triphenylphosphine)palladium 0.004mmol to the reaction In the bottle, after evacuating and circulating argon for 3 times, the reaction system was in an oxygen-free state. Under the protection of argon, ethylene glycol dimethyl ether 60mL, 2mol / L K 2 CO 3 Aqueous solution 45ml, the mixture was heated to 90 ℃ reflux Suzuki reaction 40h.
[0062] After the reaction, the reaction solution was poured into saturated ammonium chloride aqueous solution, extracted three times with dichloromethane, the organic phase was washed with sodium chloride aqueous solut...
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