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Organic room-temperature phosphorescent material with multiple stimulation responses and preparation method and application thereof

A multi-stimulus-responsive, room-temperature phosphorescence technology, applied in luminescent materials, chemical instruments and methods, applications, etc., can solve the problems of single application method, commercial application defects, low safety level, etc., to achieve a simple preparation process and promote the commercialization process. , less toxic effect

Pending Publication Date: 2021-12-03
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a class of pure organic room temperature phosphorescent materials with stimuli response and its preparation method, to solve the shortcomings of the above existing organic phosphorescent materials in anti-counterfeiting and information encryption applications: low security level, relying on crystals, application Problems such as single method, small size, poor quality and commercial application defects

Method used

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  • Organic room-temperature phosphorescent material with multiple stimulation responses and preparation method and application thereof
  • Organic room-temperature phosphorescent material with multiple stimulation responses and preparation method and application thereof
  • Organic room-temperature phosphorescent material with multiple stimulation responses and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the synthesis of compound 1:

[0068]

[0069] Weigh phenothiazine (1.99g, 10mmol), bromobenzene (1.73g, 11mmol), potassium tert-butoxide (1.34g, 12mmol), and palladium acetate (0.11g, 0.5mmol) into a 250mL Schlenk tube, nitrogen Tributylphosphine toluene solution (0.5 mL, 0.25 mmol) and 60 mL toluene were added under protection, and stirred and refluxed under N 2 atmosphere for 12 hours. After the reaction, the mixture was extracted with dichloromethane and water, and the organic phase was collected and dried over anhydrous magnesium sulfate. The organic phase of the extract was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (eluent: petroleum ether / dichloromethane=10:1) to obtain a light yellow solid. The light yellow solid was dissolved in a mixture of acetic acid and dichloromethane (1:2 by volume), and refluxed at 60°C for 24 hours. After the reaction, the mixture was extracted with dichloro...

Embodiment 2

[0070] Embodiment 2: the synthesis of compound 2:

[0071]

[0072] Weigh phenothiazine (1.99g, 10mmol), 2-bromopyridine (1.75g, 11mmol), potassium tert-butoxide (1.34g, 12mmol), and palladium acetate (0.11g, 0.5mmol) into a 250mL Schlenk tube , tributylphosphinetoluene solution (0.5mL, 0.25mmol) and 60mL toluene were added under nitrogen protection, and stirred and refluxed under N2 atmosphere for 12 hours. After the reaction, the mixture was extracted with dichloromethane and water, and the organic phase was collected and dried over anhydrous magnesium sulfate. The organic phase of the extract was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (eluent: petroleum ether / dichloromethane=3:1) to obtain a light yellow solid. The light yellow solid was dissolved in a mixture of acetic acid and dichloromethane (1:2 by volume), and refluxed at 60°C for 24 hours. After the reaction, the mixture was extracted with dichlorome...

Embodiment 3

[0073] Embodiment 3: the synthesis of compound 3:

[0074]

[0075] The weighed compound 7 (2.19g, 10mmol), elemental sulfur (0.64g, 20mmol), elemental iodine (76mg, 0.3mmol) and dichlorobenzene (6mL) were added to a 200mL schlenk tube equipped with a magneton, And stirred at 160° C. for 4 hours under the protection of nitrogen. Note that hydrogen sulfide gas is generated during the reaction, so the tail gas should be absorbed by saturated aqueous sodium hydroxide solution. After the reaction was complete, the mixture was cooled to room temperature. The mixture was separated by silica gel column chromatography (eluent: petroleum ether / dichloromethane=5:1) to obtain compound 8.

[0076] The synthesis method of compound 3 is the same as that of compound 1. Compound 3 is a white solid. M.p.249-251℃. 1 H NMR (400MHz, CDCl 3 )δ9.22(d, J=8.7Hz, 1H), 8.28(dd, J=8.0, 1.5Hz, 1H), 7.78–7.64(m, 6H), 7.49(t, J=7.5Hz, 1H), 7.43–7.35(m,3H),7.33–7.26(m,1H),6.72(d,J=9.4Hz,1H),6.54(d...

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Abstract

The invention discloses an organic room-temperature phosphorescent material with multiple stimulation responses and a preparation method and application thereof. The room-temperature phosphorescent material belongs to a host-guest blending system, the host material is mainly triphenyl phosphine oxide, the guest is mainly benzophenothiazine dioxide and derivatives thereof, and the room-temperature phosphorescent material can be prepared by physical methods such as a solvent method, a grinding method or a melting method. The preparation method of the room-temperature phosphorescent material is simple and efficient, and the room-temperature phosphorescent material has excellent performance of acid-base reversibility, acid-heat reversibility and the like. The material can realize needle type printing and thermal printing, and the object involved in the invention can be prepared into a low-concentration ethanol solution as safe ink, can be used for writing, spraying, ink-jet printing and the like, is beneficial to the application in the fields of chemical sensing, biological imaging, information encryption, anti-counterfeiting marks and the like, and is easy to realize industrialization.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and in particular relates to a preparation method of a room-temperature phosphorescent material with stimuli response and its application in needle printing, thermal printing and inkjet printing. Background technique [0002] For most organic light-emitting materials, in the process of photoluminescence, short-lived singlet excitons radiatively transition back to the ground state to emit fluorescence, and only a small part of singlet excitons can undergo intersystem crossing. The excited triplet state is reached, resulting in phosphorescence. Organic room temperature phosphorescent (RTP) materials, also known as organic long-lasting materials, are organic light-emitting materials developed in recent years with ultra-long lifetimes at room temperature. Compared with traditional fluorescent and phosphorescent materials, their lifetimes are several orders of magnit...

Claims

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Application Information

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IPC IPC(8): C07D279/22C07D279/36C07D417/04C09K11/06C09D11/50C09D11/16C09D11/30
CPCC07D279/22C07D279/36C07D417/04C09K11/06C09D11/50C09D11/16C09D11/30C09K2211/1029C09K2211/1037C09K2211/1014
Inventor 李振田瑜方曼曼杨杰
Owner TIANJIN UNIV