Bi-fluoranthene-containing organic semiconductor material, its preparation method and application
A technology of organic semiconductors and fluoranthene, which is applied in semiconductor/solid-state device manufacturing, semiconductor devices, organic chemistry, etc., can solve the problems of poor film formation, poor solubility, and low yield, and achieve simple operation and easy Controlled, easy-to-process effects
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[0031] The preparation method of the above-mentioned bisfluoranthene-containing organic semiconductor material comprises the following steps:
[0032] S1, the structural formula is The 2,7-bistrimethylsilylacetylene-9,9-diR base fluorene, the structural formula is Trimethylsilylacetylene, catalyst and first solvent (such as, triethylamine, namely NEt 3 ) into the reactor without error, after heating and reflux reaction in an oil bath for 48h, the structural formula is generated as 2,7-ditrimethylsilylacetylene-9,9-dialkylfluorene; wherein, the reactor is an oxygen-free environment (that is, an inert atmosphere composed of at least one gas of nitrogen and argon), 2,7- The molar ratio of ditrimethylsilylacetylene-9,9-diR base fluorene to trimethylsilylacetylene is 1:3; the reaction formula is as follows:
[0033]
[0034] S2. Dissolve 2,7-ditrimethylsilylacetylene-9,9-dialkylfluorene in a mixed solvent containing tetrahydrofuran (THF) and methanol (MeOH), and then dropw...
Embodiment 1
[0050] This example discloses a fluorene-containing bisfluoranthene organic compound with the following structure: 2,7-bis(7,10-diphenylfluoranthene)-9,9-dimethylfluorene (D2PFMF)
[0051]
[0052] Step 1: Preparation of Compound A: 2,7-Ditrimethylsilylacetylene-9,9-Dimethylfluorene
[0053]
[0054] In a three-necked flask with nitrogen, add the catalyst Pd(PPh 3 ) 2 Cl 2 (630mg, 0.9mmol), CuI (45mg, 0.45mmol), 2,7-dibromo-9,9-dimethylfluorene (5.28g, 15mmol), trimethylsilylacetylene (4.42g, 45mmol), and 60mL triethylamine was used as a solvent, vacuumed three times with nitrogen gas, heated to reflux in an oil bath for 48h, washed with ether and filtered, the solvent was spin-off, and n-hexane was used as an eluent for silica gel column chromatography to obtain a light yellow solid (4.5, yield 78 %). MS: m / z386. 1 H NMR (400MHz, CDCl 3 ) δ (ppm): 7.81 (d, 2H), 7.70 (d, 2H), 7.49 (t, 2H), 1.97 (s, 6H), 0.19 (s, 18H).
[0055] Step 2: Preparation of 2,7-bis(7,10-d...
Embodiment 2
[0061] This example discloses a fluorene-containing bisfluoranthene organic compound with the following structure: 2,7-bis(7,10-diphenylfluoranthene)-9,9-diethylfluorene (D2PFEF)
[0062]
[0063] Step 1: Preparation of Compound A: 2,7-Ditrimethylsilylacetylene-9,9-Diethylfluorene
[0064]
[0065] Into a three-necked flask with argon gas, add catalyst Pd(PPh 3 ) 2 Cl 2 (630mg, 0.9mmol), CuI (45mg, 0.45mmol), 2,7-dibromo-9,9-diethylfluorene (5.70g, 15mmol), trimethylsilylacetylene (4.42g, 45mmol), and 60mL of triethylamine was used as a solvent, evacuated and ventilated with argon for three times, heated and refluxed in an oil bath for 48h, washed with ether and filtered, the solvent was spin-off, and using n-hexane as an eluent for silica gel column chromatography to obtain a light yellow solid (4.97, the yield 80%). MS: m / z 414. 1 H NMR (400MHz, CDCl 3 ) δ (ppm): 7.81 (d, 2H), 7.70 (d, 2H), 7.49 (t, 2H), 1.97 (q, 4H), 1.41 (t, 6H), 0.19 (s, 18H).
[0066] Step 2...
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