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Organic room-temperature phosphorescent material as well as preparation method and application thereof

A room temperature phosphorescence, organic technology, applied in the field of preparation, organic room temperature phosphorescence materials, can solve problems such as restricting development and practical application

Inactive Publication Date: 2021-09-14
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The realization of this pure organic room-temperature phosphorescence requires rigorous molecular design, which largely restricts its further development and practical application.

Method used

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  • Organic room-temperature phosphorescent material as well as preparation method and application thereof
  • Organic room-temperature phosphorescent material as well as preparation method and application thereof
  • Organic room-temperature phosphorescent material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of compound 2FCN-PTZ

[0054] Step 1: Synthesis of intermediate PTZ-Ar-OMe

[0055]

[0056] Add phenothiazine (5g, 25.1mmol), p-bromoanisole (7.1g, 30.2mmol), sodium tert-butoxide (3.62g, 37.7mmol) in turn into a 100mL reaction flask and then add 50mL of toluene solution until dissolved, Palladium acetate (1.13g, 5.03mmol) catalyst and tri-tert-butylphosphine (0.51g, 2.51mmol) were added thereto, and reacted at 110°C for 24h under a nitrogen atmosphere. After the reaction, add water to the reaction solution, extract 3 times with dichloromethane, dry with anhydrous magnesium sulfate after the organic phases are combined, concentrate under reduced pressure, separate by silica gel column chromatography (eluent is sherwood oil: dichloromethane =2:1), a white solid PTZ-Ar-OMe (5.2 g, yield: 67.9%) was obtained.

[0057] Step 2: Synthesis of intermediate PTZ-Ar-OH

[0058]

[0059] Add PTZ-Ar-OMe (5g, 16.4mmol) to the reaction flask and a...

Embodiment 2

[0063] Embodiment 2: the synthesis of compound 2FCN-o-PTZSO

[0064]

[0065] The target product 2FCN-o-PTZ (1g, 2.3mmol) in Example 1 was dissolved in a mixture of dichloromethane (50mL), glacial acetic acid (25mL, 98%) and 30% aqueous hydrogen peroxide (1mL), and dissolved at 70 ℃ for 20 h, the reaction solution was extracted with dichloromethane, the organic phase was collected, and then anhydrous Na 2 SO 4 Dried and spin-dried to obtain the crude product. Using a mixture of petroleum ether and dichloromethane (v / v, 1:1) as an eluent, the crude product was separated and purified by silica gel column chromatography to obtain the target product 2FCN-o-PTZSO. The nuclear magnetic spectrum was as follows: figure 2 As shown, the yield was 56%.

Embodiment 3

[0066] Embodiment 3: the synthesis of compound 4FCN-o-PTZ

[0067]

[0068] Using the same synthetic method as in Example 1, first react phenothiazine with p-bromoanisole to generate PTZ-Ar-OMe, then change the methoxyl group of the intermediate product into hydroxyl group and combine with 2,3,4,5,6 - pentafluorobenzene cyanide reaction, get final product 4FCN-o-PTZ, nuclear magnetic spectrum is as image 3 As shown, the yield was 67%.

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Abstract

The invention discloses an organic room-temperature phosphorescent material as well as a preparation method and application thereof. The organic room-temperature phosphorescent material is shown as a formula (I) defined in the description. The material generates an intramolecular charge transfer state after being excited by an external light source, intersystem crossing is promoted, lone pair electrons of an oxygen bridge can enable an excited singlet state to have more n-pi * characteristics, and generation of room-temperature phosphorescence is facilitated. The material disclosed by the invention can be applied to a plurality of fields such as organic light emitting diodes, molecular sensing, anti-counterfeiting marks and biological imaging.

Description

technical field [0001] The invention relates to an organic luminescent material, in particular to an organic room-temperature phosphorescent material, a preparation method and an application. Background technique [0002] The rapid development of organic light-emitting materials has enabled them to be widely researched and applied in many fields such as optoelectronic devices and biology, including low-power lighting, high-resolution flexible displays, and high-sensitivity multi-channel biological / chemical detection. Due to the diversity of spins, organic molecules can fluoresce from singlet excitons or phosphoresce from triplet excitons. Unlike fluorescence, organic phosphorescence is rarely achieved at room temperature. Phosphorescence of organic emitters has been neglected for many years due to the inefficiency of phosphorescence in organic materials at room temperature and difficulty in observing it. In recent years, some organic molecules with extended π-conjugation a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/22C07D279/34C07D265/38C07D219/02C07D221/20C09K11/06G09F3/02
CPCC07D279/22C07D279/34C07D265/38C07D219/02C07D221/20C09K11/06G09F3/0294C07B2200/13C09K2211/1029C09K2211/1033C09K2211/1037
Inventor 蒋伟刘丹孙岳明
Owner SOUTHEAST UNIV
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