Spirofluorene derivative type organic compound and application thereof to OLEDs
A technology of organic compounds and derivatives, applied in spirofluorene derivative organic compounds and its application in OLED devices, can solve the problems of different performance and achieve stable three-dimensional structure, difficult to rotate, and large steric hindrance Effect
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Embodiment 1
[0055] Embodiment 1: the synthesis of intermediate II
[0056]
[0057] (1) Weigh raw material A and dissolve it in acetic acid, cool down to 0°C with an ice-salt bath; weigh liquid bromine and dissolve it in glacial acetic acid, and slowly add it dropwise to the acetic acid solution of raw material A, stir at room temperature for 5 hours, and the sampling point plate, showing that there is no raw material A remaining, and the reaction is complete; after the reaction, add lye to the reaction solution to neutralize, extract with dichloromethane, separate layers, take the organic phase and filter, the filtrate is rotary evaporated under reduced pressure until there is no fraction, and passes through silica gel column to obtain intermediate II; the mol ratio of intermediate II to liquid bromine is 1:1~1.5;
[0058] Take the synthesis of intermediate II-1 as an example:
[0059]
[0060] (4) Add 0.3mol of raw material A1 to a 100mL three-necked flask, dissolve 30ml of aceti...
Embodiment 2
[0065] Embodiment 2: the synthesis of compound 2:
[0066]
[0067] (1) In a 250ml three-neck flask, under the protection of nitrogen, add 0.05mol raw material I-1, 0.075mol intermediate II-1, dissolve with a mixed solvent (90ml toluene, 45ml ethanol), and then add 0.15mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0005mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate III-1 with a purity of 99.1% and a yield of 77.3%. Elemental analysis structure (molecular formula C 37 h 21 NO 3 ): theoretical value C, 84.24; H, 4.01; N, 2.65; O, 9.10; test value: C, 84.23; H, 4.02; N, 2.63; ESI-MS(m / z)(M + ): The theoretical value is 527.15, and the measured value is 527.36.
[0068] (2) In a 100ml three-necked flask, under the protection of nitrogen, add 0.03mol interme...
Embodiment 3
[0070] Embodiment 3: the synthesis of compound 13:
[0071]
[0072]
[0073] (1) In a 250ml three-neck flask, under the protection of nitrogen, add 0.05mol of raw material I-1, 0.075mol of intermediate II-2, dissolve with a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.15mol of Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0005mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate III-2 with a purity of 98.9% and a yield of 76.8%. Elemental analysis structure (molecular formula C 40 h 27 NO 2 ): theoretical value C, 86.78; H, 4.92; N, 2.53; 0, 5.78; test value: C, 86.76; H, 4.93; N, 2.55; ESI-MS(m / z)(M + ): The theoretical value is 553.20, and the measured value is 553.47.
[0074] (2) In a 100ml three-neck flask, under the protection of nit...
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