Material having crisscross structure characteristic and preparation method and application thereof
A reactive and organic technology, applied in the field of optical materials, can solve the problems of high price, limitation, and device efficiency roll-off of phosphorescent materials, and achieve the effect of high bipolar carrier transport capacity and high EQE
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preparation example 1
[0059] Preparation Example 1 Synthesis of 9,9'-(2,5-bis(pyridin-3-yl)-1,4-phenylene)bis(9H-carbazole)(compound 1)
[0060] 1. Synthesis of 1,4-difluoro-2,5-bis(3-pyridyl)benzene
[0061]
[0062] 1,4-Dibromo-2,5-difluorobenzene (1.09g, 4mmol), 3-pyridylboronic acid (1.23g, 10mmol), tetrakis(triphenylphosphine)palladium(0) (468mg, 0.4mmol ) was added into 50 mL of tetrahydrofuran, potassium carbonate aqueous solution (1M, 20 mL) was added, placed under vacuum, then backfilled with nitrogen three times, and heated at 60° C. for 16 hours under nitrogen protection. After cooling to room temperature, the layers were separated. The aqueous phase was extracted with dichloromethane (3 x 50 mL), the combined organic phases were dried over sodium sulfate, filtered and the solvent was removed. The residue was purified by column chromatography on silica gel using dichloromethane:ethyl acetate (5:1 ) as eluent to afford the product as a white solid (0.88 g, 82.0%). 1 H NMR (500MHz...
preparation example 2
[0067] Preparation example 2 Synthesis of 2',5'-bis(9H-carbazol-9-yl)-1,1':4',1"-terphenyl-4,4"-dinitrile (compound 2)
[0068] 1. Synthesis of 1,4-difluoro-2,5-bis(4-cyanophenyl)benzene
[0069]
[0070] 1,4-Dibromo-2,5-difluorobenzene (1.09g, 4mmol), (4-cyanophenyl)boronic acid (1.47g, 10mmol), tetrakis(triphenylphosphine)palladium(0)( 468 mg, 0.4) was added with THF (50 mL) and aqueous potassium carbonate (1 M, 20 mL), placed under vacuum, then backfilled with nitrogen three times, then heated in an oil bath at 60°C for 16 hours. After cooling to room temperature, the precipitate was collected, washed with dichloromethane, and dried in vacuo to obtain a white solid (1.05 g, 83.0%); 1 H NMR (500MHz, CDCl 3 ): δ=7.78(d, J=8.6Hz, 4H), 7.70(d, J=8.4Hz, 4H), 7.30(t, J=8.4Hz, 2H); 13C NMR (125MHz, CDCl 3 ): δ=138.6, 132.5, 129.5, 118.4, 118.0, 117.7, 112.5; APCI-MS m / z: 316M + ;Anal.calcd forC 20 h 10 f 2 N 2 : C, 75.94; H, 3.19; N, 8.86. Found: C, 75.95; H, 3.19; ...
preparation example 3
[0075] Preparation example 3 Synthesis of 2',5'-bis(9H-carbazol-9-yl)-1,1':4',1"-terphenyl (Compound 3)
[0076] 1. Synthesis of 1,4-difluoro-2,5-diphenylbenzene
[0077]
[0078] Add 1,4-dibromo-2,5-difluorobenzene (1.09g, 4mmol), phenylboronic acid (1.21g, 10mmol), tetrakis(triphenylphosphine)palladium(0) (468mg, 0.4mmol) THF (50 mL) and aqueous potassium carbonate (1M, 20 mL) were placed under vacuum, then backfilled three times with nitrogen, then heated in an oil bath at 60° C. for 16 hours. After cooling to room temperature, the layers were separated. The aqueous phase was extracted with dichloromethane (3 x 50 mL), the combined organic phases were dried over sodium sulfate, filtered and the solvent was removed. The residue was purified by silica gel column chromatography using dichloromethane:n-hexane (1:5) as eluent to give the product as a white solid (0.82 g, 77.1%); 1 HNMR (500MHz, CDCl 3 ): δ=7.59(d, J=7.7Hz, 4H), 7.48(dd, J=8.2, 6.8Hz, 4H), 7.44-7.38(m, ...
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