Benzothiophene derivative room-temperature phosphorescent material and preparation method thereof

A room-temperature phosphorescence and benzothiophene technology, which is applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as low lifespan, limited practical application, and few types of room-temperature phosphorescent materials

Inactive Publication Date: 2019-07-23
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a benzothiophene derivative room-temperature phosphorescent material and its preparation method, which can effectively solve the problems in the prior art that there are few types of room-temperature phosphorescent materials, limited practical applications and low service life

Method used

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  • Benzothiophene derivative room-temperature phosphorescent material and preparation method thereof
  • Benzothiophene derivative room-temperature phosphorescent material and preparation method thereof
  • Benzothiophene derivative room-temperature phosphorescent material and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0025] In this example, the benzothiophene derivative room temperature phosphorescent material was prepared according to the following reaction formula:

[0026]

[0027] Specifically: 5-bromobenzo[b]thiophene 1,1-dioxide (2.43g, 10.0mmol), phenoxazine (2.07g, 11.0mmol), Pd(OAc) 2 (0.0225g, 0.1mmol), t-BuONa (0.0192g, 0.2mmol) and P( t Bu) 3 (0.1mL) was added into a round-bottomed flask containing 100mL toluene, argon was blown for 30min, and then under argon protection, the reaction was carried out at 110°C for 72h. 100 mL) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed to obtain a crude product, which was then purified by column chromatography to obtain the product (3.1 g, 89.2%).

[0028] The H NMR spectrum data are as follows: 1 HNMR (500MHz, CDCl 3 )δ=7.88(d,J=7.5,1H),7.46(d,J=1.4,1H),7.38–7.27(m,2H),7.23–7.01(m,8H),6.67(d,J=10.8 ,1H).MS:(MALDI-TOF)m / z calcd for C 20 h 13 NO 3 S,...

Embodiment 2

[0030] In this example, the benzothiophene derivative room temperature phosphorescent material was prepared according to the following reaction formula:

[0031]

[0032] Specifically: 5-bromobenzo[b]thiophene 1,1-dioxide (2.43g, 10.0mmol), carbazole (1.83g, 11.0mmol), Pd(OAc) 2 (0.0225g, 0.1mmol), t-BuONa (0.0192g, 0.2mmol) and P( t Bu) 3 (0.1mL) was added into a round-bottomed flask containing 100mL toluene, argon was blown for 30min, and then under argon protection, the reaction was carried out at 110°C for 72h. 100 mL) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed to obtain a crude product, which was then purified by column chromatography to obtain the product (2.8 g, 84.5%).

[0033] The H NMR spectrum data are as follows: 1 H NMR (500MHz, Chloroform) δ=8.11–7.95(m,4H),7.62(dd,J=7.5,1.6Hz,1H),10.41–5.94(m,13H),8.28–5.94(m,12H), 7.48–7.18 (m, 6H), 6.67 (d, J=10.8Hz, 1H). MS: (MALDI-...

Embodiment 3

[0035] In this example, the benzothiophene derivative room temperature phosphorescent material was prepared according to the following reaction formula:

[0036]

[0037] Specifically: 5-bromobenzo[b]thiophene 1,1-dioxide (2.43g, 10.0mmol), carbazole (2.29g, 11.0mmol), Pd(OAc) 2 (0.0225g, 0.1mmol), t-BuONa (0.0192g, 0.2mmol) and P( t Bu) 3 (0.1mL) was added to a round-bottomed flask containing 100mL of toluene, argon was blown for 30min, and then under argon protection, the reaction was carried out at 110°C for 72h. After cooling to room temperature, the solvent was removed by evaporation, and then extracted with chloroform (100mL) Three times, the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed to obtain a crude product, which was then purified by column chromatography to obtain the product (3.2 g, 85.7%).

[0038] The H NMR spectrum data are as follows: 1 H NMR (500MHz, CDCl 3 )δ=7.87(s,1H),7.63(s,1H),7.51(s,1H),7.33(s,1H...

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Abstract

The invention relates to a benzothiophene derivative room-temperature phosphorescent material with room-temperature phosphorescent emission characteristics, and the phosphorescent life of a crystal can reach the ms class; and the invention also provides a preparation method of the benzothiophene derivative room-temperature phosphorescent material. The preparation method comprises the following steps: under inert gas protection, with halogen atom substituted benzothiophene sulfoxide, carbazole or phenothiazine or phenoxazine or dimethyl acridine or alkoxy as raw materials, adding a palladium catalyst, alkali, a ligand and a solvent, and reacting at 80-120 DEG C for 24 to 72 hours; then, extracting, removing the solvent, and drying to obtain a crude product; and purifying the crude product to obtain the benzothiophene derivative room-temperature phosphorescent material. The method is simple and convenient, and can effectively provide the intersystem crossing from singlet-state excitons to triplet-state excitons, so as to improve the radiative transition rate of the triplet-state excitons, promote the transition from the triplet-state excitons to ground-state excitons, and realize theroom-temperature phosphorescence emission.

Description

technical field [0001] The invention relates to the technical field of indoor phosphorescent materials, in particular to a benzothiophene derivative room temperature phosphorescent material and a preparation method thereof. Background technique [0002] Phosphorescent materials have attracted extensive attention due to their advantages such as long lifetime, long exciton transition distance, and full utilization of excited state energy. Most of the room-temperature phosphorescent (RTP) materials that have been developed so far are metal-organic compounds, because heavy metal atoms can enhance the spin-coupling effect. This type of material has broad application prospects in many fields such as storage, photocatalysis, sensors, bioimaging and organic luminescence, so it has become a very popular research field at present. However, such materials usually face disadvantages such as high price, high toxicity, difficult processing and poor flexibility. At the same time, the tri...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D409/04C07D417/04C07D333/54C09K11/06
CPCC07D333/54C07D409/04C07D413/04C07D417/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1092
Inventor 王金山姜翠凤贺盟张勤芳王伟
Owner YANCHENG INST OF TECH
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