N-diphenylphosphine oxide carbazole-9-arylfluorene sterically hindered light-emitting material and preparation method

A technology of diphenylphosphine carbazole and diphenylphosphine carbazole is applied in the field of organic light-emitting material preparation, which can solve the problems of increasing the difficulty of device fabrication, reducing device repeatability, unstable device performance and the like, and achieving a large space The effect of steric hindrance, commercialization, and simplified device structure

Inactive Publication Date: 2017-09-26
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to its low glass transition temperature (T g , 67°C) resulting in unstable device performance
[0003] Although many host materials with high triplet energy level, thermal stability and shape stability and their low-concentration doped high-efficiency phosphorescent devices have been reported, due to the inherent concentration aggregation quenching of phosphorescent materials, high-concentration doping, performance Excellent phosphorescent devices are rarely reported
The doping mechanism can effectively suppress high-concentration aggregation quenching, but its fabrication process is cumbersome and time-consuming
In addition, the performance of the device changes due to the change of the concentration, which further increases the difficulty of device fabrication, reduces the repeatability of the device, and increases the production cost

Method used

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  • N-diphenylphosphine oxide carbazole-9-arylfluorene sterically hindered light-emitting material and preparation method
  • N-diphenylphosphine oxide carbazole-9-arylfluorene sterically hindered light-emitting material and preparation method
  • N-diphenylphosphine oxide carbazole-9-arylfluorene sterically hindered light-emitting material and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: Synthesis of 3-(9-phenylfluorene)-N-diphenylphosphorcarbazole:

[0034]Take 9-hydroxy-9-phenylfluorene (0.5160g, 2mmol), N-diphenylphosphinecarbazole (0.7020g, 2mmol), dichloromethane 100mL in turn and stir to dissolve at room temperature, then add boron trifluoride diethyl ether 0.25 mL reacted for 24h. After the reaction was cooled to room temperature, about 50 mL of cold water was added to stir to quench the reaction, extracted several times with dichloromethane, and the organic phases were combined and dried over anhydrous magnesium sulfate. After drying, filter under reduced pressure, and wash the desiccant with dichloromethane, and concentrate the obtained filtrate under reduced pressure with a rotary evaporator to remove most of the solvent to obtain a concentrated crude product. Then column chromatography, with ethyl acetate and sherwood oil as detergent, after purification, white solid product 3-(9-phenylfluorene)-N-diphenylphosphocarbazole (yiel...

Embodiment 2

[0035] Example 2: Synthesis of 3,6-bis(9-phenylfluorene)-N-diphenylphosphorcarbazole:

[0036] Take 9-hydroxy-9-phenylfluorene (0.5160g, 2mmol), N-diphenylphosphinecarbazole (0.3510g, 1 mmol), and dichloromethane 100mL in turn, stir and dissolve at room temperature, and then add boron trifluoride diethyl ether 0.25 mL reacted for 24h. After the reaction was cooled to room temperature, about 50 mL of cold water was added to stir to quench the reaction, extracted several times with dichloromethane, and the organic phases were combined and dried over anhydrous magnesium sulfate. After drying, filter under reduced pressure, and wash the desiccant with dichloromethane, and concentrate the obtained filtrate under reduced pressure with a rotary evaporator to remove most of the solvent to obtain a concentrated crude product. Then column chromatography, with ethyl acetate and sherwood oil as detergent, after purification, white solid product 3,6-bis(9-phenylfluorene)-N-diphenylphospho...

Embodiment 3

[0037] Example 3: Synthesis of 3,6-bis(9-phenylfluorene)-N-diphenylphosphoroxycarbazole:

[0038] 3,6-bis(9-phenylfluorene)-N-diphenylphosphorcarbazole (0.8320g, 1mmol) was dissolved in a solvent of ethanol and chloroform and stirred, then slowly added 1.2mL of 30% hydrogen peroxide, at room temperature Stir the reaction for 5-72 hours, extract with dichloromethane several times, combine the organic phases and dry with anhydrous magnesium sulfate; after drying, filter under reduced pressure and wash the desiccant with dichloromethane, and concentrate the obtained filtrate under reduced pressure with a rotary evaporator Most of the solvent was removed to obtain a concentrated crude product; then column chromatography, using ethyl acetate and petroleum ether as detergents, purified to obtain a white solid product 3,6-bis(9-phenylfluorene)-N-diphenyl Phosphate oxycarbazole. (Yield: 43%). LC-MS (EI) m / z 848.3061 [M + ].

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Abstract

The synthesis and application of N-diphenylphosphoroxycarbazole-9-arylfluorene sterically hindered organic light-emitting materials relate to third-generation light-emitting display materials and technologies. The present invention is a kind of N-diphenylphosphoroxycarbazole The azole/9-arylfluorene sterically hindered organic light-emitting material has a specific design structure as follows: it specifically relates to the preparation method and application in organic light-emitting diode devices. The material has: (1) high triplet energy level; (2) excellent luminous efficiency, high thermal stability and stable amorphous form; (3) three-dimensional large-volume steric hindrance effect can effectively suppress quenching and The dimer emits light; (4) the synthesis method is simple and feasible. A blue organic electroluminescent device was prepared with its preliminary structure as the host material. It shows that this kind of compound has broad application prospect and potential commercial value in phosphorescent organic light-emitting diodes as host materials.

Description

technical field [0001] The invention specifically relates to a preparation method based on replacing the 9-position hydroxyl group of 9-hydroxyl-9-arylfluorene with N-diphenylphosphorylcarbazole to make it functional, and belongs to the technical field of organic light-emitting materials preparation. Background technique [0002] Over the past few decades, breakthroughs have been made in the research of phosphorescent organic light-emitting devices (PhOLEDs). Phosphorescent OLEDs were first discovered by Thompson and Forrest. Due to the existence of heavy metal spin-orbit coupling, singlet and triplet excitons can be utilized, so that the internal quantum efficiency can theoretically reach 100%. Compared with traditional fluorescent organic light-emitting diodes with an internal quantum efficiency of 25%, phosphorescent organic light-emitting diodes (PhOLEDs) have greater commercial application value, so they are regarded as the most promising full-color display and solid-s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/572C07F9/6558C09K11/06
CPCC07F9/5728C07F9/65583C07F9/65586C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092
Inventor 赵祥华黎小胜唐林王莉敏
Owner XINYANG NORMAL UNIVERSITY
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