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Organic long afterglow material containing triphenylphosphine (triphenylphosphine oxide) and preparation method and use method thereof

A long afterglow material, triphenyl technology, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of late start of research and development of organic long afterglow materials and limited types, and achieve long afterglow luminescence and easy purification. , the effect of suppressing non-radiative transitions

Pending Publication Date: 2020-11-13
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Due to the late start of research and development of organic long-lasting materials, their types are still very limited. Therefore, the design and synthesis of efficient organic long-lasting materials is still one of the challenges in the field of optoelectronic materials.

Method used

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  • Organic long afterglow material containing triphenylphosphine (triphenylphosphine oxide) and preparation method and use method thereof
  • Organic long afterglow material containing triphenylphosphine (triphenylphosphine oxide) and preparation method and use method thereof
  • Organic long afterglow material containing triphenylphosphine (triphenylphosphine oxide) and preparation method and use method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Synthesis of intermediate [2-iodotriphenylamine]

[0032]

[0033]Under a nitrogen atmosphere, add diphenylamine (2.00g, 11.82mmol) into a 250mL dry three-necked flask, then add 1,2-diiodobenzene (4.68g, 14.18mmol), add 50mL toluene to dissolve, add o-phenanthroline ( 255.58mg, 1.42mmol), cuprous iodide (225.08mg, 1.18mmol) and potassium hydroxide (2.65g, 47.27mmol), heated to 110°C and stirred for 16h. After the reaction, the toluene was removed from the reaction solution by rotary evaporation, and 50 ml of dichloromethane was added to dissolve it, then the reaction solution was poured into a separatory funnel, and washed with water for 2-3 times. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was spin-dried in a rotary evaporator, and then purified by silica gel column chromatography, and the eluent was a mixture of dichloromethane and n-hexane with a volume ratio of 1:2. solution. 2.00 g of yellow-white solid was obtain...

Embodiment 2

[0038] Synthesis of target product P2

[0039]

[0040] Add Example 1 (0.40 g, 0.93 mmol) into a round-bottomed flask, and dissolve in 20 ml of tetrahydrofuran. 6 mL of hydrogen peroxide aqueous solution (30%) was added, and after stirring for 5 hours, 50 mL of dichloromethane and 50 mL of water were added to the reaction liquid, followed by liquid separation. The dichloromethane layer was spin-dried with a rotary evaporator to obtain a white powder. The white powder was recrystallized from dichloromethane / n-hexane to obtain 0.35 g of white solid with a yield of 84.4%.

Embodiment 3

[0042] (1) Synthesis of intermediate 2-bromotriphenylphosphine

[0043]

[0044] With reference to step (2) in Example 1, 2-bromotriphenylphosphine was synthesized by using o-bromoiodobenzene instead of 2-iodotriphenylamine. (59.2% yield)

[0045] (2) Synthesis of intermediate 2-bromotriphenylphosphine oxide

[0046]

[0047] Referring to the steps in Example 2, 2-bromotriphenylphosphine oxide was synthesized by using 2-bromotriphenylphosphine instead of 2-dianilinotriphenylphosphine. (yield is 81.5%)

[0048] (3) Synthesis of target product 2-(2-diphenylamino)phenyltriphenylphosphine oxide

[0049]

[0050] Add 2-boronate triphenylamine (1.25g, 3.36mmol), 2-bromotriphenylphosphine oxide (1.00g, 2.80mmol) and sodium hydroxide (0.34g, 8.40mmol) into a 250mL three-necked flask, add Appropriate amount of ethylene glycol dimethyl ether, add a teaspoon of tetrakistriphenylphosphine palladium in a nitrogen environment. Raise the temperature to 110°C and react for 12h. ...

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Abstract

The invention relates to an organic long afterglow material containing triphenylphosphine (triphenylphosphine oxide). The molecular structure of the organic long afterglow material is TP(O)-R, whereinTP(O) is a triphenylphosphine (triphenylphosphine oxide) group; R is an aromatic ring or an aromatic heterocyclic compound; TP(O) and R groups are connected in an ortho-position mode, the synthesizedluminescent material has a spiral molecular configuration, non-radiative transition is effectively inhibited under the large steric hindrance configuration and strong intramolecular action, long afterglow luminescence is achieved, and the luminescence wavelength, phosphorescence lifetime and other properties of a final product can be adjusted by introducing different functional groups. The synthesis method disclosed by the invention is simple in process and easy to purify, the synthesized luminescent material has the spiral molecular configuration, the non-radiative transition is effectivelyinhibited under the large steric hindrance configuration and strong intramolecular action, the long afterglow luminescence is realized, and the luminescence wavelength, phosphorescence lifetime and other properties of the final product can be adjusted by introducing different functional groups. The organic long afterglow material is applied to the fields of organic photoelectricity, biological imaging, counterfeiting prevention and the like.

Description

technical field [0001] The invention belongs to the technical field of organic long-lasting afterglow materials, and relates to an organic long-lasting afterglow material containing triphenyl (oxygen) phosphine, a preparation method and a use method thereof, and its use as a luminescent material in organic electroluminescent devices, biological imaging and anti-counterfeiting, etc. field applications. Background technique [0002] Long afterglow luminescence refers to the ability to maintain luminescence for more than a few seconds after the excitation light source is removed (when the duration of luminescence exceeds 0.1s and the brightness exceeds 0.32mcd / m 2 , can be well distinguished and identified by naked eyes, see literature: Xu S, Chen R, Zheng C, Huang W. Excited State Modulation for Organic Afterglow: Materials and Applications. Adv. Mater., 2016, 28(45): 9920 -9940.) A photoluminescence phenomenon, also known as persistent luminescence. Long afterglow luminesce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50C07F9/53C09K11/06
CPCC07F9/5022C07F9/5072C07F9/5325C09K11/06C09K2211/1007C09K2211/1014
Inventor 于涛谢宗良王海兰黄成董孟阳孙浩东黄维
Owner NORTHWESTERN POLYTECHNICAL UNIV
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