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A kind of benzothiadiazole luminescent material containing diphenylphosphine oxide and its preparation and application

A technology of benzothiadiazole and diphenylphosphine oxide is applied in the fields of benzothiadiazole luminescent materials and preparation and application, which can solve problems such as scarcity of luminescent materials, and achieve high product yield, convenient purification, and high solids. The effect of photoluminescence efficiency

Active Publication Date: 2017-10-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, looking at the current progress in this field, high-efficiency near-infrared (luminescent wavelength greater than 650nm) luminescent materials are still very scarce.

Method used

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  • A kind of benzothiadiazole luminescent material containing diphenylphosphine oxide and its preparation and application
  • A kind of benzothiadiazole luminescent material containing diphenylphosphine oxide and its preparation and application
  • A kind of benzothiadiazole luminescent material containing diphenylphosphine oxide and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Dissolve 3-bromothiophene (10.5g, 63.9mmol), 1-naphthaleneboronic acid (10g, 58.1mmol) in toluene (120mL), Na 2 CO 3 In the mixture of aqueous solution (2mol / L, 58mL) and ethanol (10mL), stir and degas with a syringe needle for 30 minutes, and quickly add tetrakis(triphenylphosphine)palladium (336mg, 0.29mmol), the reaction temperature is 80°C, After heating to reflux for 8 h under the protection of nitrogen, it was cooled to room temperature and extracted with dichloromethane. Anhydrous MgSO for organic layer 4 Dry, filter, remove the solvent under reduced pressure, and then separate with a silica gel column. The eluent is petroleum ether. The crude product is refluxed with ethanol to obtain 3-(1-naphthyl)thiophene as a white solid. The above reaction is shown in the following formula:

[0042]

[0043] 3-(1-naphthyl)thiophene (10g, 47.6mmol) and 3.64g LiClO 4 -SiO 2 (1:4) was added into dichloromethane (80ml), stirred evenly, and then N-bromosuccinimide (N...

Embodiment 2

[0055] (1) Add 1-naphthaleneboronic acid (5.16g, 30mmol), s-tribromobenzene (11.3g, 36mmol), toluene (80mL), ethanol (10mL), and 2M sodium carbonate aqueous solution (30mL) into two-necked flasks, and pass Exhaust by bubbling nitrogen gas for 30 minutes. The catalyst tetrakis(triphenylphosphine)palladium (173mg, 0.15mmol) was quickly added into the reaction flask, and then heated to 90°C for 8 hours under reflux. After the mixture was cooled, it was washed with distilled water and extracted with toluene, and the organic phase was extracted with MgSO 4 After drying, the white solid 1-naphthyl-3,5-dibromobenzene was obtained by column chromatography. The above reaction is shown in the following formula:

[0056]

[0057] 1-Naphthyl-3,5-dibromobenzene (18.1g, 50mmol) was dissolved in 150mL of dry tetrahydrofuran, protected with nitrogen, and cooled to -78°C with liquid nitrogen / isopropanol. Slowly added n-BuLi (2.5M, 20 mL, 50 mmol) dropwise into the reaction flask, the mix...

Embodiment 3

[0065] Step (1) and step (2) are identical with embodiment 2.

[0066] (3) 3-(1-naphthyl)-5-(diphenylphosphoryl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaboryl -2-yl)benzene (2.26g, 4.4mmol), 4,7-bis(5-bromothiophen-2-yl)-2,1,3-benzothiadiazole (0.916g, 2mmol) was dissolved in toluene (50mL), ethanol (10mL), 2M aqueous sodium carbonate solution (4mL), and exhaust by bubbling nitrogen gas for 30 minutes. The catalyst tetrakis(triphenylphosphine)palladium (69mg, 0.06mmol) was quickly added into the reaction flask, and then heated to 90°C for reflux reaction for 12 hours. Cool to room temperature and extract with toluene. Anhydrous MgSO for organic layer 4 Dry, filter, and separate with a silica gel column after removing the solvent under reduced pressure, and reflux the crude product with n-hexane to obtain the red solid product 4,7-bis(5-(3-(1-naphthyl)-5-(diphenylphosphine) Base) phenylthiophen-2-yl) benzothiadiazole.Above-mentioned reaction is shown in the following formula:

...

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Abstract

The invention belongs to the technical field of organic luminescent materials, and discloses a benzothiadiazole luminescent material containing diphenylphosphine oxide, as well as its preparation and application. The preparation method is as follows: using bromide of benzene, thiophene, carbazole, fluorene, anthracene, pyrene, or pyridine as the reaction raw material, through two-step reaction to obtain diphenylphosphino-substituted borate or tributyltin-substituted intermediate body, and then react this intermediate with 4,7-dibromobenzothiadiazole or 4,7-bis(5-bromothiophen-2-yl)-2,1,3 benzothiadiazole to obtain The precursor of the diphenylphosphine compound is finally oxidized by an oxidant to obtain a benzothiadiazole light-emitting material containing diphenylphosphine oxide. The luminescent material of the invention has better electron injection and transport properties, can prepare luminescent materials with luminescent colors such as red, green, and blue, and has important application prospects in electroluminescence display, lighting and laser devices.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a benzothiadiazole luminescent material containing diphenylphosphine oxide and its preparation and application. Background technique [0002] In the past three decades, researchers have made great progress in the fields of high-efficiency organic light-emitting materials and organic light-emitting diodes (Organic Light-Emitting Diode, OLED). Since the operating voltage of organic light-emitting diodes is usually lower than 10V, the luminous brightness exceeds 1000cd / m 2 (much higher than the brightness of ordinary TV screens), the luminous efficiency and lifespan meet its requirements as a light-emitting device and lighting, which prompts its commercial application process to continue to advance. [0003] Since the invention of OLED, small-molecule luminescent materials have been an important research direction for researchers, and they have the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/12C09K11/06C07F9/6558C07F9/6541H01L51/54
Inventor 李远武颖
Owner SOUTH CHINA UNIV OF TECH
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