Stilbene derivative as well as preparation and application thereof

A technology of stilbene and derivatives, which is applied in the field of preparation of luminescent organic substances, can solve problems such as low solubility and high fluorescence quenching effect, and achieve the effect of reducing fluorescence quenching

Pending Publication Date: 2022-05-20
MINDU INNOVATION LAB +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the currently reported blue-light core emission structures, the stilbene structural unit has unique photoelectric properties, and trans-stilbene derivatives have become research hotspots because of their good photoelectrochemical properties, but because of their low solubility , high fluorescence quenching effect, the production, purification, processing and device use of trans-stilbene derivatives face many restrictions, and are not favored by actual production applications

Method used

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  • Stilbene derivative as well as preparation and application thereof
  • Stilbene derivative as well as preparation and application thereof
  • Stilbene derivative as well as preparation and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0048] Preparation of 4-(1-adamantyl)bromobenzene:

[0049] Add adamantanol (2.0g, 13.14mmol) and bromobenzene (2.0631g, 13.14mmol, 1eq) into a 250ml two-necked flask, dissolve in 80ml of dry dichloromethane, and slowly add trifluoroethylene dropwise at -5°C under nitrogen protection. Methanesulfonic acid (5.9162g, 39.42mmol, 3eq). React for 3 hours. Raise to 25°C, add saturated aqueous sodium carbonate solution until the reaction solution is neutral. The organic phase was extracted and separated, and the organic phase was washed twice with saturated brine. The organic phase was concentrated to dryness under reduced pressure and purified by column chromatography (n-hexane) to obtain 2.87 g of 4-(1-adamantane)bromobenzene (S1), with a yield of 75%. The physical property data obtained by proton nuclear magnetic resonance spectrum are as follows: 1 H NMR (400MHz, CDCl 3): δ=7.42(dt, J=8.68, 2.76Hz, 2H), 7.23(dt, J=8.64, 2.68Hz, 2H), 2.09(s, 3H), 1.87(d, J=2.6Hz, 6H) ,1.76(d...

Embodiment 1

[0057] Preparation of 4,4'-bis(4-(3-(1-adamantyl)-9carbazolyl)styryl)-1,1'-biphenyl (target product):

[0058] 4-[3-(1-adamantyl)-9H-carbazol-9-yl]benzaldehyde (S4) (1.4g, 3.452mmol) and 4,4'-bis(diethoxyphosphonoform Base) biphenyl (0.6289g, 1.381mmol, 1eq) was mixed into a 250ml two-necked flask, 100ml of tetrahydrofuran was added, potassium tert-butoxide (0.7747g, 6.904mmol, 5eq) was added in batches, and reacted for 3h. The reaction solution was concentrated under reduced pressure, the obtained product was washed twice with water and twice with methanol, and the product was purified by recrystallization (toluene) to obtain 0.95 g of 4,4'-bis(4-(3-(1-adamantyl)-9carba Azolyl) styryl) -1,1'-biphenyl (a-BSBCz), yield 71.8%. The physical property data obtained by proton nuclear magnetic resonance spectrum are as follows: 1 H NMR (400MHz, CD 2 Cl 2 ): δ=8.20(d, J=7.84Hz, 2H), 8.17(d, J=1.6Hz, 2H), 7.84(d, J=8.48Hz, 4H), 7.75(dd, J=5.68, 8.52Hz ,8H),7.64(d,J=8.40Hz,4H),7.56...

Embodiment 2

[0060] Film preparation of 4,4'-bis(4-(3-(1-adamantyl)-9carbazolyl)styryl)-1,1'-biphenyl:

[0061] Put 4,4'-bis(4-(3-(1-adamantyl)-9carbazolyl)styryl)-1,1'-biphenyl in a quartz crucible and put it into a coating machine for evaporation In the coil, select the substrate, use deionized water, acetone, and isopropanol as solvents, ultrasonically for 15 minutes, blow dry with a nitrogen gun, and ultraviolet ozone for 20 minutes, and put it into the substrate bottom plate of the coating machine. The pressure in the inner cavity of the coating machine is pumped below 5×10-4Pa, and the average evaporation rate can be monitored to be 0.6 Evaporate to a thickness of 120nm to obtain a pure film of 4,4'-bis(4-(3-(1-adamantyl)-9carbazolyl)styryl)-1,1'-biphenyl.

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Abstract

The invention discloses a stilbene derivative containing adamantyl carbazole as well as a preparation method and application of the stilbene derivative, and the stilbene derivative is prepared by reacting carbazolyl benzaldehyde containing adamantyl with 4, 4 '-bis (diethoxy phosphonomethyl) biphenyl. The compound can be processed into a high-performance film through vacuum evaporation to prepare a high-performance OLED device, can be used as a dark blue light organic electroluminescent material, and has a wide application prospect.

Description

technical field [0001] The application relates to a stilbene derivative containing an adamantyl group, and belongs to the field of preparation of light-emitting organic substances. Background technique [0002] Since the 21st century, organic semiconductor light-emitting materials have developed rapidly. Compared with traditional inorganic light-emitting materials, the preparation and processing of organic semiconductor light-emitting materials are more environmentally friendly and cost less. Devices processed with organic light-emitting materials have good mechanical flexibility, biocompatibility, more diverse uses, and lower harm to humans. At the same time, organic semiconductor light-emitting materials are tunable, and theoretically can achieve fluorescence emission at any wavelength. However, organic light-emitting materials still face many challenges at present, especially the types of light-emitting materials for deep blue light are few, and their practicability is ...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06C23C14/12C23C14/26H01L51/50H01L51/54
CPCC07D209/86C09K11/06C23C14/12C23C14/26C09K2211/1007C09K2211/1029H10K85/6572H10K50/11Y02E10/549
Inventor 宋玲边广岭吴厚霖赵晓凡
Owner MINDU INNOVATION LAB
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