A kind of organic photoelectric material and its application

Abstract

The invention involves an organic optoelectronic material and its purpose.The organic photoelectric material includes organic compounds with structural characteristics as shown in (1), and the organic compound has a small ΔE (S 1 Tadpole 1 ), Easy to obtain good thermal delayed fluorescent characteristics, thereby achieving high efficiency and long life of OLED devices.The synthesis process of compounds is relatively simple and low in cost, so it has huge application potential and scope of application.The invention also involves a mixture containing the organic compound, a composition (printed ink) and organic electronic devices, especially the electro -lit device.

Description

technical field

[0001] The present invention relates to the field of organic optoelectronic materials, in particular to an organic compound with thermally excited delayed fluorescence characteristics, a composition, a mixture thereof and its application in organic electronic devices, especially in organic electroluminescent devices . The invention also relates to an organic electronic device containing the compound, especially an electroluminescent device, and its application in displays and lighting devices. Background technique

[0002] The diversity and synthesis of organic electroluminescent materials have laid a solid foundation for the realization of large-area new display devices. In order to improve the luminous efficiency of organic light emitting diodes (OLEDs), currently, fluorescent and phosphorescent luminescent material systems have been developed. OLEDs using fluorescent materials are characterized by high reliability, but their internal electroluminescence ...

Examples

Embodiment 1

[0190]

[0191]

[0192] 15-(4,6-diphenyl-1,3,5-triazinyl-2-yl)-5,10-diphenyl-10,15-dihydro-5H-pyrrole[3,2-c : 4,5-c'] dicarbazole

[0193] Add 4.98g, 10mmol 5,10-diphenyl-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']dicarbazole, 0.36g, 15mmol hydrogenation to a 250ml three-necked flask Sodium, 100ml THF, in N 2 In the atmosphere, stir at room temperature for 30min, add 2.97g, 11mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine in batches, and react at 60°C for 12 hours. Bring to room temperature. The reaction solution was poured into water, washed to remove sodium hydride, and then suction filtered to obtain a solid product, which was dissolved in dichloromethane to remove impurities therein. Recrystallize with toluene / ethanol to obtain the product solid powder 15-(4,6-diphenyl-1,3,5-triazinyl-2-yl)-5,10-diphenyl-10,15-di Hydrogen-5H-pyrrole[3,2-c:4,5-c']biscarbazole 6.2 g. MS (ASAP) = 729.3.

Embodiment 2

[0195]

[0196] 5,10-Diphenyl-15-(4′-(11-phenylindole[3,2-b]carbazole-5(11H)-yl)-[1,1′-diphenyl] -4-yl)-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']bicarbazole

[0197] Add 4.98g, 10mmol 5,10-diphenyl-10,15-dihydro-5H-pyrrole [3,2-c:4,5-c']dicarbazole, 6.2g, 11mmol 5- (4'-bromo-[1,1'-diphenyl]-4-yl)-11-phenyl-5,11-dihydroindolo[3,2-b]carbazole, 6.9g, 50mmol carbonic acid Potassium, 0.26g, 1mmol 18-crown-6, 3.0g, 15mmol cuprous iodide and 150ml o-dichlorobenzene, in N 2 In the atmosphere, react at 160°C, track the progress of the reaction by TLC, and cool down to room temperature after the reaction is completed. Pour the reaction solution into water, wash to remove K 2 CO 3 , and then suction filtered to obtain a solid product, which was washed with dichloromethane. Recrystallize with dichloromethane and ethanol to obtain the product 5,10-diphenyl-15-(4'-(11-phenylindole[3,2-b]carbazole-5(11H)-yl) -[1,1'-diphenyl]-4-yl)-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']bicarbazole 8.0g,...

Embodiment 3

[0199]

[0200] 15-(3-(4-([1,1′:3′,1″-tetraphenyl]-5′-yl)-6-phenyl-1,3,5-triazinyl-2-yl )phenyl)-5,10-diphenyl-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']biscarbazole

[0201] Add 4.98g, 10mmol5,10-diphenyl-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']dicarbazole, 5.94g, 11.0mmol2 to a 250ml three-necked flask -([1,1′:3′,1″-tetraphenyl]-5′-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine, 6.9 g, 50mmol potassium carbonate, 0.26g, 1mmol18-crown-6, 3.0g, 15mmol cuprous iodide and 150ml o-dichlorobenzene, in N 2 In the atmosphere, react at 160°C, track the progress of the reaction by TLC, and cool down to room temperature after the reaction is completed. Pour the reaction solution into water, wash to remove K 2 CO 3, and then suction filtered to obtain a solid product, which was washed with dichloromethane. Recrystallize with a mixed solvent of toluene / petroleum ether to obtain the product white solid powder 15-(3-(4-([1,1′:3′,1″-tetraphenyl]-5′-yl)-6-benzene Base-1,3,5-triazinyl-2-yl)...

technical field

[0001] The present invention relates to the field of organic optoelectronic materials, in particular to an organic compound with thermally excited delayed fluorescence characteristics, a composition, a mixture thereof and its application in organic electronic devices, especially in organic electroluminescent devices . The invention also relates to an organic electronic device containing the compound, especially an electroluminescent device, and its application in displays and lighting devices. Background technique

[0002] The diversity and synthesis of organic electroluminescent materials have laid a solid foundation for the realization of large-area new display devices. In order to improve the luminous efficiency of organic light emitting diodes (OLEDs), currently, fluorescent and phosphorescent luminescent material systems have been developed. OLEDs using fluorescent materials are characterized by high reliability, but their internal electroluminescence ...

Examples

Embodiment 1

[0190]

[0191]

[0192] 15-(4,6-diphenyl-1,3,5-triazinyl-2-yl)-5,10-diphenyl-10,15-dihydro-5H-pyrrole[3,2-c : 4,5-c'] dicarbazole

[0193] Add 4.98g, 10mmol 5,10-diphenyl-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']dicarbazole, 0.36g, 15mmol hydrogenation to a 250ml three-necked flask Sodium, 100ml THF, in N 2 In the atmosphere, stir at room temperature for 30min, add 2.97g, 11mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine in batches, and react at 60°C for 12 hours. Bring to room temperature. The reaction solution was poured into water, washed to remove sodium hydride, and then suction filtered to obtain a solid product, which was dissolved in dichloromethane to remove impurities therein. Recrystallize with toluene / ethanol to obtain the product solid powder 15-(4,6-diphenyl-1,3,5-triazinyl-2-yl)-5,10-diphenyl-10,15-di Hydrogen-5H-pyrrole[3,2-c:4,5-c']biscarbazole 6.2 g. MS (ASAP) = 729.3.

Embodiment 2

[0195]

[0196] 5,10-Diphenyl-15-(4′-(11-phenylindole[3,2-b]carbazole-5(11H)-yl)-[1,1′-diphenyl] -4-yl)-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']bicarbazole

[0197] Add 4.98g, 10mmol 5,10-diphenyl-10,15-dihydro-5H-pyrrole [3,2-c:4,5-c']dicarbazole, 6.2g, 11mmol 5- (4'-bromo-[1,1'-diphenyl]-4-yl)-11-phenyl-5,11-dihydroindolo[3,2-b]carbazole, 6.9g, 50mmol carbonic acid Potassium, 0.26g, 1mmol 18-crown-6, 3.0g, 15mmol cuprous iodide and 150ml o-dichlorobenzene, in N 2 In the atmosphere, react at 160°C, track the progress of the reaction by TLC, and cool down to room temperature after the reaction is completed. Pour the reaction solution into water, wash to remove K 2 CO 3 , and then suction filtered to obtain a solid product, which was washed with dichloromethane. Recrystallize with dichloromethane and ethanol to obtain the product 5,10-diphenyl-15-(4'-(11-phenylindole[3,2-b]carbazole-5(11H)-yl) -[1,1'-diphenyl]-4-yl)-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']bicarbazole 8.0g,...

Embodiment 3

[0199]

[0200] 15-(3-(4-([1,1′:3′,1″-tetraphenyl]-5′-yl)-6-phenyl-1,3,5-triazinyl-2-yl )phenyl)-5,10-diphenyl-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']biscarbazole

[0201] Add 4.98g, 10mmol5,10-diphenyl-10,15-dihydro-5H-pyrrole[3,2-c:4,5-c']dicarbazole, 5.94g, 11.0mmol2 to a 250ml three-necked flask -([1,1′:3′,1″-tetraphenyl]-5′-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine, 6.9 g, 50mmol potassium carbonate, 0.26g, 1mmol18-crown-6, 3.0g, 15mmol cuprous iodide and 150ml o-dichlorobenzene, in N 2 In the atmosphere, react at 160°C, track the progress of the reaction by TLC, and cool down to room temperature after the reaction is completed. Pour the reaction solution into water, wash to remove K 2 CO 3, and then suction filtered to obtain a solid product, which was washed with dichloromethane. Recrystallize with a mixed solvent of toluene / petroleum ether to obtain the product white solid powder 15-(3-(4-([1,1′:3′,1″-tetraphenyl]-5′-yl)-6-benzene Base-1,3,5-triazinyl-2-yl)...

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