Thermally activated delayed fluorescent blue light material, its synthesis method and application

A technology of thermally activated delayed and blue-light materials, which is applied in the field of organic light-emitting materials, can solve the problems of limited applications, and achieve the effects of low singlet triplet energy level difference, high photoluminescence quantum yield, and fast reverse intersystem crossing constant

Active Publication Date: 2020-12-25
WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Not only that, due to the very wide spectrum of thermally activated delayed fluorescent materials, and the exciton lifetime on the order of microseconds, their application in mass-produced device structures is greatly limited.

Method used

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  • Thermally activated delayed fluorescent blue light material, its synthesis method and application
  • Thermally activated delayed fluorescent blue light material, its synthesis method and application
  • Thermally activated delayed fluorescent blue light material, its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Synthesis of thermally activated delayed fluorescent blue light material

[0029] The synthetic route is shown in the reaction formula:

[0030]

[0031] Weigh 3.19g of raw material 1 (5mmol), 4.00g of 9,10-dihydro-9,9-diphenylacridine (12 mmol), 0.18g of palladium acetate (0.8mmol) and 0.68g of tri-tert-butylphosphine Tetrafluoroborate (2.4mmol), pour in the 250mL two-necked bottle, transfer the two-necked bottle containing the reaction raw materials to the glove box, then add 2.34gNaOt-Bu (24mmol) to the two-necked bottle in the glove box ), then injected 100 mL of toluene that had been dehydrated and deoxygenated under an argon atmosphere, and reacted at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 1:3) to obtain Light blue powder 2...

Embodiment 2

[0034] Embodiment 2: the synthesis of thermally activated delayed fluorescent blue light material

[0035] The synthetic route reaction formula is shown as:

[0036] Weigh 3.19g raw material 1 (5mmol), 2.20g phenoxazine (12mmol), 0.18g palladium acetate (0.8 mmol) and 0.68g tri-tert-butylphosphine tetrafluoroborate (2.4mmol), pour into 250mL di transfer the two-necked bottle containing the reaction materials to the glove box, then add 2.34 gNaOt-Bu (24mmol) to the two-necked bottle in the glove box, inject 100mL of NaOt-Bu (24mmol) into the two-necked bottle under an argon atmosphere, and remove the water beforehand. Oxygen toluene, reacted at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 1:3) to obtain Light blue powder 2.1g, yield 49%.

[0037] The obtai...

Embodiment 3

[0039] Embodiment 3: the synthesis of thermally activated delayed fluorescent blue light material

[0040] The synthetic route is shown in the reaction formula:

[0041]Weigh 3.19g raw material 1 (5mmol), 2.34g3,6-dimethylcarbazole (12mmol), 0.18g palladium acetate (0.8mmol) and 0.68g tri-tert-butylphosphine tetrafluoroborate (2.4mmol) Pour it into a 250mL two-necked bottle, transfer the two-necked bottle containing the reaction materials to the glove box, then add 2.34g NaOt-Bu (24mmol) to the two-necked bottle in the glove box, and inject 100mL of Toluene, which had been dehydrated and deoxygenated in advance, was reacted at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 1:3) to obtain Light blue powder 2.6g, yield 60%.

[0042] The obtained product, i.e....

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Abstract

The present invention relates to the technical field of organic luminescent materials, in particular to a thermally activated delayed fluorescent blue light material, its synthesis method and application; the thermally activated delayed fluorescent blue light material has the following general formula: The thermally activated delayed fluorescent blue light material provided by the present invention , novel structure, low singlet triplet energy level difference, fast reverse intersystem crossing constant (kRISC) and high photoluminescence quantum yield (PLQY); by fine-tuning the structure of the electron acceptor unit, making them With different electron acceptance capabilities, fine-tuning of the spectrum in the deep blue range is realized.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to a thermally activated delayed fluorescent blue light material, its synthesis method and application. Background technique [0002] Organic Light Emitting Diode (OLED) is a sandwich-type device composed of electrode / light-emitting layer / electrode structure invented by Chinese-American professor Deng Qingyun and others. When a current passes through it, a strong electric field will drive the organic light-emitting layer in the middle of the device electrodes to emit light. Based on the electroluminescence phenomenon of OLEDs, OLEDs are widely used in information display and solid-state lighting and other fields. [0003] The continuous renewal of organic light-emitting materials has greatly promoted the development of OLED technology. Generally speaking, fluorescent materials belong to the first generation, and transition metal complex phosphorescent materia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D219/02C07D413/14C07D401/14C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07D219/02C07D413/14C07D401/14C07F7/0816C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/104H10K85/657H10K85/40H10K85/6572H10K50/11H10K2101/20C09K2211/1014H10K50/16H10K50/17
Inventor 罗佳佳黄金昌杨林张曲
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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