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Phosphino-oxy boron complex dark-blue photo-thermal excitation delayed fluorescence material as well as synthesis method and application thereof

A phosphine oxide boron, delayed fluorescence technology, applied in the field of thermally excited delayed fluorescent materials, can solve the problems of quenching, triplet-triplet annihilation concentration, etc., to improve efficiency, reduce quenching effect, and improve electron injection and transmission. effect of ability

Inactive Publication Date: 2019-11-22
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 problem that the existing blue light-emitting guest materials are prone to triplet-triplet annihilation and concentration quenching phenomena, and to provide a deep blue light thermally excited delayed fluorescent material of a phosphine oxide boron complex, Synthetic methods and their applications

Method used

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  • Phosphino-oxy boron complex dark-blue photo-thermal excitation delayed fluorescence material as well as synthesis method and application thereof
  • Phosphino-oxy boron complex dark-blue photo-thermal excitation delayed fluorescence material as well as synthesis method and application thereof
  • Phosphino-oxy boron complex dark-blue photo-thermal excitation delayed fluorescence material as well as synthesis method and application thereof

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specific Embodiment approach 1

[0034] Specific embodiment 1: In this embodiment, the structural formula of the phosphine-oxy-boron complex deep blue light-thermal excitation delayed fluorescence material is as follows:

[0035]

[0036] When X is a diphenylphosphineoxy group and Y is H, its structural formula is:

[0037]

[0038] When X is a diphenylphosphineoxy group and Y is a diphenylphosphineoxy group, its structural formula is:

[0039]

specific Embodiment approach 2

[0040] Specific embodiment two: the synthetic method of the phosphine oxide boron complex deep blue light thermally excited delayed fluorescent material in the specific embodiment one, the synthetic method is as follows:

[0041] 1. Dissolve 3-5mmol of 3,6-di-tert-butylcarbazole in dichloromethane and place it in the reaction flask, and dissolve 5-10mmol of N-bromosuccinimide in dimethylformamide , poured into a constant pressure dropping funnel and added dropwise at room temperature, stirred the reaction at room temperature until the dropwise addition was completed, extracted with water and dichloromethane, combined the organic layers, and removed the organic solvent after drying to obtain a crude product, which was drenched with petroleum ether. Purified by detergent column chromatography to obtain 1-bromo-3,6-di-tert-butyl-9-methyl-9H-carbazole or 1,8-dibromo-3,6-di-tert-butyl-9H-carbazole azole.

[0042]2. After placing the product synthesized in 3~5mml step 1, palladium ...

specific Embodiment approach 3

[0044] Specific embodiment three: the difference between this embodiment and specific embodiment two is that in step one, 5 mmol of 3,6-di-tert-butylcarbazole is dissolved in dichloromethane and placed in a reaction flask, and 50 mmol of N-bromo Succinimide was dissolved in dimethylformamide. Others are the same as in the second embodiment.

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Abstract

The invention relates to a thermal excitation delayed fluorescence material, and a synthesis method and application thereof, and particularly discloses a phosphino-oxy boron complex dark-blue photo-thermal excitation delayed fluorescence material, and a synthesis method and application thereof, in order to solve a problem of concentration quenching of dark blue light TADF materials and a problem that electroluminescent devices are low in efficiency and rapid in attenuation. The structural formula of the material is shown in the description. The method comprises the following steps: preparing 1-bromo-3,6-di-tert-butyl-9H-carbazole or 1,8-dibromo-3,6-di-tert-butyl-9H-carbazole; preparing (3,6-di-tert-butyl-9H-carbazol-1-yl)diphenyl phosphine oxide or (3,6-di-tert-butyl-9H-carbazol-1,8-diyl)bis(diphenylphosphine oxide), thereby obtaining a final product. According to the material, the efficiency of the electroluminescent device is remarkably improved, the quenching effect is reduced, andthe efficiency stability of the electroluminescent device is enhanced. The invention belongs to the field of preparation of fluorescent materials.

Description

technical field [0001] The invention relates to a heat-excited delayed fluorescent material, a synthesis method and an application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have the characteristics of low energy consumption, rich colors, fast response, and flexible devices, and are considered to be the most promising next-generation flat-panel display and solid-state lighting technologies. At present, research on OLEDs has made remarkable progress. The internal quantum efficiency (IQE) of the first-generation OLED based on fluorescent emitting materials is only 25% because it only utilizes singlet excitons to emit light. The second-generation OLED is based on noble metal phosphorescent emission materials, which comprehensively utilize singlet (25%) and triplet (75%) excitons through the spin-orbit coupling (SOC) between noble metals and their ligands, and the IQE can reach 100%. . However, phosphorescent emitting materials have the follo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F9/572H01L51/50H01L51/54
CPCC09K11/06C07F9/5728C09K2211/1029C09K2211/1007C09K2211/1014H10K85/6572H10K50/00
Inventor 陶李林韩春苗
Owner HEILONGJIANG UNIV
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