Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof

A phosphorescent host, luminescent material technology, applied in luminescent materials, organic chemistry, electrical solid devices, etc., can solve the problem of ineffective use of triplet exciton energy, achieve large steric hindrance effect, mild conditions, good photoelectric performance Effect

Inactive Publication Date: 2013-03-20
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the spin-forbidden state of triplet excitons in organic electroluminescent materials, the energy of triplet excitons cannot be effectively used, so the quantum efficiency of the device has always been limited to 25%.

Method used

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  • Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof
  • Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof
  • Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: 9-(2-pyridyl)-9-(2-thienyl)fluorene

[0045] 9-Hydroxy-9(2-pyridyl)fluorene (0.5180 g, 2 mmol), thiophene (1.28 mL, 16 mmol), and 200 mL of acetic acid were heated and stirred in turn to dissolve, then 4 mL of concentrated sulfuric acid was added and heated to 120°C for 24 h. After the reaction was cooled to room temperature, about 100 mL of cold water was added and stirred, then an aqueous sodium hydroxide solution was added until the solution was alkaline, extracted several times with dichloromethane, and the combined organic phases were 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 petroleum ether as detergents, after purification, a white solid product was obtained (y...

Embodiment 2

[0046] Embodiment 2: Synthesis of 9-(2-pyridyl)-9-(2-methylthienyl)fluorene:

[0047] 9-Hydroxy-9(2-pyridyl)fluorene (0.5180 g, 2 mmol), 2-methylthiophene (1.57 mL, 16 mmol), 200 mL of acetic acid were heated and stirred to dissolve in turn, and then 4 mL of concentrated sulfuric acid was added and heated to Reflux at 120°C for 24h. After the reaction was cooled to room temperature, about 100 mL of cold water was added and stirred, then an aqueous sodium hydroxide solution was added until the solution was alkaline, extracted several times with dichloromethane, and the combined organic phases were 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 petroleum ether as detergents, after purificatio...

Embodiment 3

[0048] Example 3: Synthesis of 9-(2-pyridyl)-9-(2-(2,2-bithienyl))fluorene:

[0049] Take 9-hydroxy-9(2-pyridyl)fluorene (0.5180 g, 2 mmol), 2,2-dithiophene (0.1663 g, 1 mmol), 200 mL of acetic acid and heat and stir to dissolve in turn, then add 4 mL of concentrated sulfuric acid Heated to 120 ° C reflux for 24h. After the reaction was cooled to room temperature, about 100 mL of cold water was added and stirred, then an aqueous sodium hydroxide solution was added until the solution was alkaline, extracted several times with dichloromethane, and the combined organic phases were 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 petroleum ether as detergents, after purification, a white solid pr...

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Abstract

The invention provides a pyridine-fluorene organic electrophosphorescence main body luminescent material and a preparation method thereof, relating to new-generation organic luminescent display materials and technology. Due to the rigid structure, the luminescent material has high triplet energy level and favorable hole injection and transmission performance; and due to the three-dimensional large-volume steric hindrance effect, the luminescent material has stable amorphous state, and thus, can be widely used in organic light-emitting diodes. The specific design structure of the pyridine-fluorene main body material is disclosed in the specification. The invention particularly relates to a preparation method and application in organic light-emitting diode devices. The material has the advantages of high luminescence efficiency, high heat stability, high glass transition temperature and simple synthesis method, and can effectively inhibit concentration quenching and dimer luminescence. The preliminary structure as the main body material implements red-green-blue tricolor organic electroluminescent devices. The compounds have wide application prospects and huge commercial value in the aspects of electrophosphorescent main body materials.

Description

technical field [0001] The invention specifically relates to a preparation method based on substituting the 9-hydroxyl group of 9-hydroxyl-9-(2-pyridyl)fluorene with an aromatic ring to make it functional, and relates to the steps and raw materials used in the preparation process of these materials. Background technique [0002] Since Deng Qingyun reported the organic light-emitting diodes with high brightness and low voltage and sandwich structure in 1987, organic light-emitting diodes, as the next generation flat panel display and solid-state lighting technology, have been highly valued by the majority of scientific workers and greatly appreciated by industrial elites. Research enthusiasm. Compared with displays made of inorganic materials, organic electroluminescent display devices have many advantages beyond their reach, such as: wide source of materials, low energy consumption, light weight, small size, simple manufacturing process, high contrast, wide viewing angle, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/16C07D213/06C07D409/10C07D409/14C07D401/14C07D401/10C09K11/06H01L51/54
Inventor 解令海黄维赵祥华仪明东张广维常永正张效霓
Owner NANJING UNIV OF POSTS & TELECOMM
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