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Multi-functional modified phenyl ether single phosphine oxide main material, synthetic method and application thereof

A host material and multi-functional technology, which can be used in chemical instruments and methods, luminescent materials, compounds of Group 5/15 elements of the periodic table, etc., and can solve the problems of low luminous efficiency and brightness, and high turn-on voltage.

Inactive Publication Date: 2013-02-06
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to solve the contradiction between the low luminous efficiency and brightness of the existing organic electroluminescent materials, the high triplet excited state energy level and the good carrier injection / transport ability, which lead to its application as the main body material The problem of high turn-on voltage of electroluminescent devices, and provide multifunctional modified phenyl ether-based monophosphine oxide host materials, synthesis methods and applications

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  • Multi-functional modified phenyl ether single phosphine oxide main material, synthetic method and application thereof
  • Multi-functional modified phenyl ether single phosphine oxide main material, synthetic method and application thereof
  • Multi-functional modified phenyl ether single phosphine oxide main material, synthetic method and application thereof

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specific Embodiment approach 1

[0096] Embodiment 1: The synthesis method of the multifunctional modified phenylene ether-based monophosphine oxide host material in this embodiment is realized in the following steps:

[0097] 1. Synthesis of bromodiphenylphosphineoxyphenyl ether:

[0098] Dissolve every mmol of 2-diphenylphosphineoxyphenyl ether (DPESPO) in 2-6ml of concentrated sulfuric acid with a mass concentration of 98%, and mix N-bromosuccinimide and 2-diphenylphosphineoxy The molar ratio of the base phenyl ether is a: 1. Add N-bromosuccinimide, stir for 2-4 hours, and then use CH 2 Cl 2 and H 2 O extraction to obtain an organic layer, the obtained organic layer was dried with anhydrous sodium sulfate, then put into a rotary evaporator to spin dry, and then recrystallized with absolute ethanol to obtain brominated diphenylphosphineoxyphenyl ether;

[0099] 2. Dissolve every mmol of brominated diphenylphosphineoxyphenyl ether prepared in step 1 in 5-20ml of tetrahydrofuran, and add boric acid ester w...

specific Embodiment approach 2

[0118] Specific embodiment 2: The synthesis method of the multifunctional modified phenylene ether-based monophosphine oxide host material in this embodiment is realized according to the following steps:

[0119] 1. Synthesis of bromodiphenylphosphineoxyphenyl ether:

[0120] Dissolve every mmol of 2-diphenylphosphineoxyphenyl ether (DPESPO) in 2-6ml of concentrated sulfuric acid with a mass concentration of 98%, and mix N-bromosuccinimide and 2-diphenylphosphineoxy The molar ratio of the base phenyl ether is a: 1. Add N-bromosuccinimide, stir for 2-4 hours, and then use CH 2 Cl 2 and H 2 O extraction to obtain an organic layer, the obtained organic layer was dried with anhydrous sodium sulfate, then put into a rotary evaporator to spin dry, and then recrystallized with absolute ethanol to obtain brominated diphenylphosphineoxyphenyl ether;

[0121] Two, add carbazole, salt of wormwood, cuprous iodide and 18 crown 6 in the brominated diphenylphosphineoxyphenyl ether prepare...

specific Embodiment approach 3

[0126] Specific embodiment three: the synthesis method of the multifunctional modified phenylene ether-based monophosphine oxide host material in this embodiment is realized according to the following steps:

[0127] 1. Synthesis of bromodiphenylphosphineoxyphenyl ether:

[0128] Dissolve every mmol of 2-diphenylphosphineoxyphenyl ether (DPESPO) in 4ml of concentrated sulfuric acid with a mass concentration of 98%. The molar ratio of ether substance is 1:1, add N-bromosuccinimide, stir and react for 4h, and then use CH 2 Cl 2 and H 2 O extraction to obtain an organic layer, the obtained organic layer was dried with anhydrous sodium sulfate, then put into a rotary evaporator to spin dry, and then recrystallized with absolute ethanol to obtain brominated diphenylphosphineoxyphenyl ether;

[0129] 2. Dissolve every mmol of brominated diphenylphosphineoxyphenyl ether prepared in step 1 in 10ml of tetrahydrofuran, add 9,9-diethylfluorene borate, tetrabutylammonium bromide and te...

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Abstract

The invention discloses a multi-functional modified phenyl ether single phosphine oxide main material, a synthetic method and an application thereof, relates to an organic electroluminescence material, preparation and application thereof and solves the problems of low luminous efficiency and brightness of existing organic electroluminescence materials and contradiction between high triplet state excited state energy level and good carrier injection / transmitting capacity. The preparing method of parent structure of the multi-functional modified phenyl ether single phosphine oxide main material includes adding N-bromo-succinimide in 2-diphenyl phosphine oxide phenylate to perform bromination reaction; and introducing a functional group with a carrier transmission characteristic to perform a substitution reaction, and extraction, drying and column chromatography are performed to obtain the multi-functional modified phenyl ether single phosphine oxide main material. The multi-functional modified phenyl ether single phosphine oxide main material has the advantages that the voltage of lightening an electrophosphorescent device is reduced, the luminous efficiency and brightness of the organic electroluminescence material are improved, and the material is mainly used for an organic electrophosphorescent diode device.

Description

technical field [0001] The present invention relates to organic electroluminescence material, synthesis and application. Background technique [0002] 1997 reported the first organic electrophosphorescent device using organic transition metal complexes as light emitters in "Nature", and found that electrophosphorescent materials can simultaneously use singlet and triplet excitons to emit light, and its theoretical internal quantum efficiency can reach 100%, aroused widespread concern and research. In recent years, organic light-emitting diodes (OLEDs) based on phosphorescent materials have attracted much attention due to their outstanding advantages such as small size, light weight, flexibility, high luminous efficiency, and fast response. However, due to the long excited state lifetime of the electrophosphorescent material itself, there are serious concentration quenching and triplet-triplet annihilation effects, which greatly reduce the luminous efficiency and brightnes...

Claims

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Application Information

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IPC IPC(8): C07F9/53C07F9/572C09K11/06H01L51/54H01L51/56
Inventor 许辉韩春苗
Owner HEILONGJIANG UNIV
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