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Aggregation-state luminescent material with high efficiency and narrow half-peak width

A technology of luminescent materials and aggregation state, which is applied in the direction of luminescent materials, semiconductor/solid-state device manufacturing, semiconductor devices, etc., and can solve problems such as poor color purity, difficulty in adjusting luminescent light color, and inability to meet the high color purity of full-color display technology.

Active Publication Date: 2020-06-19
SUZHOU UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Up to now, the introduction of TADF materials as luminescent dyes in OLED devices can achieve high efficiency, but in most cases the color purity is very poor, which cannot meet the technical requirements of high color purity for full-color display technology. The material system needs to be developed urgently
In recent years, although new TADF materials with multiple resonance effects (MR) have been reported to achieve high color purity luminescence, (Adv. Mater., 28, 2777-2781 (2016); Nat. Photonics (2019) DOI: 10.1038 / s41566 -019-0476-5; Angew.Chem.Int.Ed.,57,11316-11320(2018);Adv.Opt.Mater.,1801536(2019);ACS Appl.Mater.Interfaces 11,13472-13480(2019 )), but it is difficult to adjust the light color

Method used

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  • Aggregation-state luminescent material with high efficiency and narrow half-peak width
  • Aggregation-state luminescent material with high efficiency and narrow half-peak width
  • Aggregation-state luminescent material with high efficiency and narrow half-peak width

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the synthesis of compound TOAT

[0046]

[0047] Compound 1 (methyl anthranilate) and compound 2 (methyl o-iodobenzoate) can be obtained directly;

[0048] Compound 3: Under nitrogen protection, add compound 1 (3.02g, 20mmol), compound 2 (13.10g, 50mmol), activated copper powder (0.64g, 10mmol), copper iodide (0.95g , 5mmol), 18-crown-6 (0.26g, 1mmol) and potassium carbonate (16.56g, 120mmol), and then added 100mL o-dichlorobenzene solvent, heated to reflux for 48h. After the reaction was complete, cool to room temperature, filter and collect the lower organic phase, dry over anhydrous sodium sulfate, and concentrate in vacuo with a rotary evaporator. Using petroleum ether: ethyl acetate (3:1) as the eluent, it was further purified by silica gel column chromatography to obtain 4.36 g of white solid with a yield of 52%.

[0049] Product characterization: 1 H NMR (600MHz, CDCl 3 ,ppm): δ7.59(dd,J=7.7Hz,1.6Hz,3H),7.38-7.34(m,3H),7.10-7.05(m,6H),3.37(s,...

Embodiment 2

[0054] Embodiment 2: the synthesis of compound 3PhTOAT

[0055]

[0056] Compound 4: Compound 3 (3.77g, 9mmol), silver nitrate (9.17g, 54mmol) and iodine (10.28g, 40.5mmol) were sequentially added to a 500mL flask, and 300mL ethanol solvent was added, and the reaction was stirred at room temperature for 12h. After the reaction was complete, an equivalent amount of sodium sulfite solution was added until the solution was colorless, the lower organic phase was collected by filtration, dried over anhydrous sodium sulfate, and concentrated in vacuo with a rotary evaporator. Using PE:EA (5:1) as the eluent, it was further purified by silica gel column chromatography to obtain 6.17 g of white solid with a yield of 86%.

[0057] Product characterization: 1 H NMR (600MHz, CDCl 3 , ppm): δ7.91(d, J=2.2Hz, 3H), 7.64(dd, J=8.6Hz, 2.2Hz, 3H), 6.77(d, J=8.7Hz, 3H), 3.43(s, 9H ). 13 C NMR (151MHz, CDCl 3 ,ppm): δ165.58,145.75,141.17,139.54,129.27,127.64,87.05,52.12.MS(MALDI-TOF).Cal...

Embodiment 3

[0064] Embodiment 3: the synthesis of compound 3PTPTOAT

[0065]

[0066] Compound 7: Under nitrogen protection, compound 4 (1.59g, 2mmol), 4-tert-butylphenylboronic acid (1.60g, 9mmol), tetrakis (triphenylphosphine) palladium (0.31g, 0.27 mmol and potassium carbonate (2.48g, 18mmol), then add toluene (60mL), ethanol (20mL) and deionized water (9mL) as a solvent, and heat to reflux for 12h. After the reaction is cooled to room temperature, wash with dichloromethane and deionized Ion water is extracted, and the lower organic phase is collected, dried over anhydrous sodium sulfate, and concentrated in vacuo with a rotary evaporator.Using petroleum ether: ethyl acetate (5:1) as eluent, further purified by silica gel column chromatography to obtain yellow Green solid 1.49g, yield 91%.

[0067] Product characterization: 1 H NMR (600MHz, CDCl 3 ,ppm): δ7.87(d,J=2.3Hz,3H),7.63(dd,J=8.5Hz,2.4Hz,3H),7.55-7.53(m,6H),7.47-7.45(m,6H) ,7.20(d,J=8.5Hz,3H),3.41(s,9H),1.36(s,27H). 13 ...

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Abstract

The invention discloses a novel aggregation-state luminescent material with high efficiency and narrow half-peak width, namely an azatriene derivative, a preparation method of the azatriene derivativeand application of the azatriene derivative in an electronic device, and further relates to the electronic device. Particularly, the azatriene derivative shows weak monomer fluorescence emission in adilute solution, shows an obvious red shift luminescence spectrum different from monomer fluorescence characteristics in an aggregation state and has extremely high fluorescence quantum yield and efficient thermal activation delayed fluorescence property. Therefore, the electronic device prepared by taking the azatriene as the fluorescent dye has the advantages of high efficiency and high color purity.

Description

technical field [0001] The present invention relates to the technical field of organic luminescent dyes, in particular to a new type of highly efficient and narrow half-width aggregated luminescent material—azatriene derivatives, its preparation method and its use in electronic devices. The present invention also relates to the the electronic device itself. Background technique [0002] Organic luminescent dyes have a wide range of applications in electronic devices. For example, in an organic electroluminescent device (OLED), by connecting a voltage across the cathode (Al) and the anode (ITO), the carrier electrons and holes are respectively injected, and the electrons and holes are respectively passed through the electron transport layer ( ETL) and hole transport layer (HTL) reach the emissive layer (EML) containing organic luminescent dyes, in the emissive layer (EML), electrons and holes recombine to generate excitons that emit photons in the process of fluorescence or ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/16C09K11/06H01L51/50H01L51/54
CPCC07D471/16C09K11/06C09K2211/1059H10K85/636H10K85/6572H10K50/11
Inventor 张晓宏王凯范孝春安达千波矢土屋阳一田中正树
Owner SUZHOU UNIV
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