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Organic blue fluorescent material and preparation method thereof, and organic electroluminescent device

A technology of blue fluorescent and fluorescent materials, applied in the application field of organic optoelectronic materials, can solve the problems of low exciton luminescence efficiency and unfavorable external quantum efficiency, and achieve the effects of excellent blue light performance, good blue light emission, and high external quantum efficiency.

Active Publication Date: 2022-03-29
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is well known that in organic fluorescent materials, the triplet excitons of thermally activated delayed fluorescence (TADF) materials pass through T 1 to S 1 The reverse intersystem crossing conversion of the reverse intersystem into singlet excitons, thus effectively improving the utilization of excitons (η s ), its exciton utilization rate (η s ) exceeds 90%, however, the luminous efficiency of excitons in this material (η pl ) is low, which is also unfavorable for the improvement of external quantum efficiency

Method used

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  • Organic blue fluorescent material and preparation method thereof, and organic electroluminescent device
  • Organic blue fluorescent material and preparation method thereof, and organic electroluminescent device
  • Organic blue fluorescent material and preparation method thereof, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] An organic blue fluorescent material with the following structure:

[0063]

[0064] The synthetic route of above-mentioned organic blue fluorescent material is as follows:

[0065]

[0066] 9,9'-dioctyl-2,7-dibromofluorene (7.5mmol, 4.125g), 4-cyanophenylboronic acid (5mmol, 735mg), 2M potassium carbonate aqueous solution (10mL) and 50mL of toluene solvent Add it into a 250mL two-necked flask, stir slowly at room temperature, evacuate nitrogen, and add tetrakis(triphenylphosphine)palladium (Pd(pph 3 ) 4 ) (288 mg), continue vacuuming and blowing nitrogen, slowly raise the temperature to reflux at 110°C, stop the reaction after the reaction is completed, and cool to room temperature. Extract with water and dichloromethane, collect the organic layer, add an appropriate amount of anhydrous magnesium sulfate to remove excess water, filter, spin the liquid to dryness and concentrate, and then separate and purify through a chromatographic column to obtain the product...

Embodiment 2

[0077] An organic blue fluorescent material with the following structure:

[0078]

[0079] The synthetic route of the organic blue fluorescent material shown in the above formula structure is as follows:

[0080]

[0081] The specific preparation method is:

[0082] The preparation of product M1 is the same as in Example 1.

[0083] 3,6-dibromocarbazole (10mmol, 3.24g), tetrabutylammonium bromide (201mg), potassium hydroxide aqueous solution (1.74g, 7mL) and 50mL of toluene solvent were added in a 250mL two-necked flask, room temperature Under slow stirring, vacuum nitrogen, under nitrogen atmosphere, add bromohexane (12mmol, 1.98g), continue vacuum nitrogen, slowly heat up to 110 ° C reflux, stop the reaction after the reaction is completed, and cool to room temperature. Extract with water and dichloromethane, collect the organic layer, add an appropriate amount of anhydrous magnesium sulfate to remove excess water, filter, spin the liquid to dryness and concentrate, a...

Embodiment 3

[0096] An organic blue fluorescent material with the following structure:

[0097]

[0098] The synthetic route of the organic blue fluorescent material of above-mentioned structure is as follows:

[0099]

[0100] The specific preparation method is:

[0101] The preparation of product M1 is the same as in Example 1.

[0102] M1 (5mmol, 2.845g), biboronic acid pinacol ester (5mmol, 1.27g), potassium acetate (2g) and 50mL of N,N-dimethylformamide solvent were added to a 250mL two-necked flask, at room temperature Stir slowly, vacuum nitrogen, under nitrogen atmosphere, add 1,1'-bis(di-phenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl 2 ) (183 mg), continue vacuuming and blowing nitrogen, slowly heat up to 60 ° C, stop the reaction after the reaction is completed, and cool to room temperature. Extract with water and dichloromethane, collect the organic layer, add an appropriate amount of anhydrous magnesium sulfate to remove excess water, filter, spin the liqui...

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Abstract

The invention discloses an organic blue fluorescent material, a preparation method thereof, and an organic electroluminescent device. The organic blue fluorescent material has the general structural formula of the following formula I, formula II, formula III or formula IV: D-π-A, formula I; A-π-D-π-A, formula II; wherein, D represents the electron donor group of the organic blue fluorescent material, π represents the intermediate connecting π bridging group of the organic blue fluorescent material, and A represents the electron acceptor group of the organic blue fluorescent material. The organic blue fluorescent material of the present invention has good blue light-emitting performance, and the organic electroluminescent device prepared by using it as a light-emitting layer shows high-quality dark blue light-emitting performance, stable device efficiency, and no obvious efficiency roll-off phenomenon , and the device has a high maximum external quantum efficiency.

Description

technical field [0001] The invention belongs to the technical field of application of organic photoelectric materials, and in particular relates to an organic blue fluorescent material, a preparation method thereof, and an organic electroluminescent device. Background technique [0002] Organic electroluminescent devices (OLEDs) have the advantages of light and thin appearance, strong environmental adaptability, and flexible display. As a new generation of flat-panel displays, they have broad market application prospects. Compared with red and green light materials, blue light has a wider band gap, which is not conducive to the injection and transport of electrons and holes, so its device efficiency is lower and its performance is poorer, and commercial applications cannot be realized. Therefore, this patent aims at designing and synthesizing an organic blue light-emitting material with a new structure, further improving device efficiency and stability, and achieving the pur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07C255/58C07C253/30C07F5/04C07C255/51C09K11/06H01L51/50H01L51/54
Inventor 王华吴董宇孙静武钰铃赵波苗艳勤高龙王子琪刘幸卢国婧许并社吴玉程
Owner TAIYUAN UNIV OF TECH
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