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Sky blue light thermal activation delayed fluorescence material and preparation method and application thereof

A delayed fluorescence, photothermal technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., to achieve the effect of small single-triplet energy level difference, improved efficiency, highest brightness and high current efficiency

Active Publication Date: 2020-04-24
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Based on the above background, the existing technology solutions in material design and device preparation still need to be improved and developed

Method used

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  • Sky blue light thermal activation delayed fluorescence material and preparation method and application thereof
  • Sky blue light thermal activation delayed fluorescence material and preparation method and application thereof
  • Sky blue light thermal activation delayed fluorescence material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 Synthesis of TB-o-X series sky blue light materials

[0052]

[0053] (1) Synthesis of TB-o-DCz:

[0054]1. Add 1,3-dibromo-2-iodobenzene (1.8g, 5mmol) into a 100mL Chirank bottle, inject 60mL of anhydrous and oxygen-free diethyl ether under an argon atmosphere, and put it into minus 78°C for freezing and stirring , then inject 5ml of n-butyl lithium in n-hexane solution (1mmol / mL), react at -78°C for 2 hours, then add bis(trimethylphenyl)boron fluoride (1.34g, 5mmol), react at -78°C for 24 hours Warm up to room temperature, pour the reaction solution into 300mL 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, 1:1) to obtain White powder 2g (TB-o-DBr), yield 83%. MS (EI) m / z: 482.00.

[0055] 2. Add TB-o-DBr (2.41g, 5mmol), carbazole (Cz, 2.00g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetraf...

Embodiment 2

[0060] Example 2 Synthesis of TB-m-X series sky blue light materials

[0061]

[0062] (1) Synthesis of TB-m-DCz:

[0063] Add TB-m-DBr (2.41g, 5mmol), carbazole (Cz, 2.00g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate ( 0.34g, 1.2mmol), and then NaOt-Bu (1.16g, 12mmol) was added into the glove box, and 80mL of toluene, which had been dehydrated and deoxygenated beforehand, was injected under an argon atmosphere, and reacted at 120°C for 48 hours. Cool to room temperature, pour the reaction solution into 300mL 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 Sky blue powder 2.2g, yield 66%. The final product was purified using a sublimation apparatus, and finally 1.7 g of the target compound, sky blue photothermally activated delayed fluorescence material TB-m-DCz, was obtained. M...

Embodiment 3

[0068] Example 3 Synthesis of DTB-X series sky blue light materials

[0069]

[0070] (1) Synthesis of DTB-Cz:

[0071] Add DTB-Br (3.26g, 5mmol), carbazole (Cz, 1.00g, 6mmol), palladium acetate (45mg, 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17g , 0.6mmol), then NaOt-Bu (0.58g, 6mmol) was added into the glove box, and 60mL of toluene, which had been dehydrated and deoxygenated beforehand, was poured into the glove box under an argon atmosphere, and reacted at 120°C for 48 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, 1:1) to obtain Sky blue powder 3.0g, yield 81%. The final product was purified using a sublimation apparatus, and finally 2.1 g of the target compound DTB-Cz, a photothermally activated delayed fluorescence material, was obtained. MS (...

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Abstract

The invention belongs to the field of organic light-emitting devices, and particularly relates to a sky blue light thermal activation delayed fluorescence material and a preparation method and an application thereof. The sky blue light thermal activation delayed fluorescence material is at least one of compounds with chemical structural formulas shown as formulas I-VII. According to the invention,triphenylboron with weak electron accepting capability and large space structure is used as an electron withdrawing group; a palladium-catalyzed C-N coupling method is applied to be connected with different electron donor groups to obtain the sky blue light thermal activation delayed fluorescent material, and the thermal activation delayed fluorescent material has very small single triplet stateenergy level difference, sky blue light emission and high PLQY.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent devices, and in particular relates to a sky-blue light-thermally activated delayed fluorescent material and a preparation method and application thereof. Background technique [0002] Organic light-emitting diode (OLED) does not require a backlight for its active luminescence, high luminous efficiency, large viewing angle, fast response, wide temperature range, relatively simple production and processing technology, and low driving voltage , low energy consumption, lighter and thinner, flexible display and other advantages and huge application prospects have attracted the attention of many researchers. In OLEDs, the dominant light-emitting guest material is crucial. The luminescent guest materials used in early OLEDs are fluorescent materials. Since the ratio of singlet and triplet excitons in OLEDs is 1:3, the theoretical internal quantum efficiency (IQE) of OLEDs based on fluorescent m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02H01L51/54
CPCC07F5/027C09K11/06C09K2211/1029C09K2211/1014C09K2211/1007H10K85/6572Y02B20/00
Inventor 刘源欧阳敏婷李彦辰
Owner GUANGDONG UNIV OF TECH
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