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Diphenyl sulfone-based bipolar blue phosphor host material and preparation method and apparatus thereof

A host material, blue phosphorescence technology, applied in electroluminescent diodes, the field of bipolar blue phosphorescence host materials, can solve the problems such as the structure of blue light devices needs to be simplified, and achieve easy large-scale preparation and high-efficiency device performance , The preparation method is simple and feasible

Inactive Publication Date: 2014-04-02
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, sulfone-based bipolar host blue phosphorescent material molecules are rare, and the structure of its blue light device needs to be simplified, and there is still room for improvement in performance

Method used

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  • Diphenyl sulfone-based bipolar blue phosphor host material and preparation method and apparatus thereof
  • Diphenyl sulfone-based bipolar blue phosphor host material and preparation method and apparatus thereof
  • Diphenyl sulfone-based bipolar blue phosphor host material and preparation method and apparatus thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of formula 2 compound

[0041] In a 500ml three-necked flask, add 8.91g (30mmol) of 4-bromodiphenylsulfone, 8.4g (33mmol) of pinacol ester of diboronic acid, 8.8g (90mmol) of anhydrous potassium acetate, [1,1'-bis(di Phenylphosphorus)ferrocene]palladium dichloride 1.2g, dioxane 200ml, reflux reaction under nitrogen protection for 24h. Cool to room temperature, add 200ml of water, then extract with dichloromethane (2*200ml), combine the organic layers, dry over anhydrous sodium sulfate, and concentrate to obtain an oil. After column chromatography, the volume ratio of ethyl acetate:petroleum ether=1:20~1:5 was eluted to obtain 8.5 g of white solid with a yield of 82.31%. 1 HNMR (300MHz, CDCl 3 )δ (ppm): 7.94-7.92 (m, 6H), 7.57-7.45 (m, 3H), 1.32 (s, 12H). 1 See attached for HNMR spectrum figure 1 .

Embodiment 2

[0042] Embodiment 2: the preparation of formula 4 compound

[0043] In a 500ml three-necked flask, add 6.05g (17.6mmol) of the compound of formula 2 obtained above, 3.28g (8mmol) of 3,6-dibromo-9-phenylcarbazole, 1.0g of tetrakis(triphenylphosphine)palladium, 20ml of potassium carbonate aqueous solution (4.3g of potassium carbonate dissolved in 20ml of water), 40ml of ethanol and 200ml of toluene were mixed evenly, and the reaction was refluxed under nitrogen protection for 24h. The reaction solution was cooled to room temperature, then extracted with dichloromethane (2*200ml), the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to obtain an oil. After column chromatography, the volume ratio of ethyl acetate:petroleum ether=1:10~1:3 was eluted to obtain 2.5 g of white solid with a yield of 45.21%. 1 HNMR (300MHz, CDCl 3 )δ (ppm): 8.38 (s, 2H), 8.06-8.00 (m, 8H), 7.85-7.82 (d, J=8.4Hz, 4H), 7.67-7.46 (m, 15H). 1 See attached for HNMR spect...

Embodiment 3

[0044] Embodiment 3: the preparation of formula 6 compound

[0045] In a 500ml three-necked flask, add 6.05g (17.6mmol) of the compound of formula 2 obtained above, 3.28g (8mmol) of 2,7-dibromo-9-phenylcarbazole, 1.0g of tetrakis(triphenylphosphine)palladium, 20ml of potassium carbonate aqueous solution (4.3g of potassium carbonate dissolved in 20ml of water), 40ml of ethanol and 200ml of toluene were mixed evenly, and the reaction was refluxed under nitrogen protection for 24h. The reaction solution was cooled to room temperature, then extracted with dichloromethane (2*200ml), the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to obtain an oil. After column chromatography, the volume ratio of ethyl acetate:petroleum ether=1:10~1:3 was eluted to obtain 2.7g of white solid with a yield of 48.82%. 1 HNMR (300MHz, CDCl 3 )δ(ppm):8.25-8.22(d,J=8.7Hz,2H),8.04-7.99(t,J=8.1Hz,4.5Hz,8H),7.75-7.78(d,J=8.4Hz,4H) ,7.69-7.53(m,15H). 1 See attached ...

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Abstract

The invention discloses a diphenyl sulfone-based bipolar blue phosphor host material, which is formed by diphenyl sulfone with electronic transmission ability and a carbazole group with hole transmission ability. The structural formula of the diphenyl sulfone-based bipolar blue phosphor host material is shown in a formula (I) as shown in the specification, wherein R1 is one of phenyl, ethyl, n-propyl, isopropyl, cyclohexyl and triphenyl silicon; R2-R5 are the same in structure, and are one of (2-phenyl sulfuryl) phenyl, (3-phenyl sulfuryl) phenyl or (4-phenyl sulfuryl) phenyl, substituted at 2,7-bit of carbazole or substituted at 3,6-bit of the carbazole. The blue phosphor host material disclosed by the invention is short in synthetic route, simple and feasible in synthetic method, and applicable to wide application. The blue phosphor apparatus manufactured by the host material disclosed by the invention has the advantages of high brightness, high efficiency, low lighting start voltage and the like, and can be widely applied to the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the field of luminescent materials, and in particular relates to a diphenyl sulfone-containing bipolar blue phosphorescence host material, a preparation method and its application in electroluminescent diodes. Background technique [0002] Organic electroluminescent devices (OLEDs) have attracted great attention because of their strong self-emission performance, short response time, wide viewing angle, high contrast ratio, and light weight. It has broad application prospects in the next generation of flat panel display and solid-state lighting technologies. [0003] At present, in organic small molecule electrophosphorescent devices, green phosphorescent and red phosphorescent devices have made great progress, and many green and red materials that can be used in organic electrophosphorescent diodes (PhOLEDs) have been found, and these materials are used to make PhOLEDs have the advantages of high luminous efficiency, pure chro...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/86H01L51/54
Inventor 蒋伟黄斌孙岳明班鑫鑫刘媛媛范文娟尹智慧施法臣
Owner SOUTHEAST UNIV