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Diazosulfide light-emitting material containing diphenyl phosphine oxide and preparation method and application thereof

A technology of benzothiadiazole and diphenylphosphine oxide is applied in the fields of benzothiadiazole luminescent materials and preparation and application, which can solve the problems of scarcity of luminescent materials, and achieve high product yield, convenient purification and good solubility Sexual and film-forming effects

Active Publication Date: 2016-01-20
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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  • Diazosulfide light-emitting material containing diphenyl phosphine oxide and preparation method and application thereof
  • Diazosulfide light-emitting material containing diphenyl phosphine oxide and preparation method and application thereof
  • Diazosulfide light-emitting material containing diphenyl phosphine oxide and preparation method and application thereof

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 3.64gLiClO 4 -SiO 2 (1:4) was added into dichloromethane (80ml), stirred evenly, and then N-bromosuccinimide (NB...

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 light-emitting materials, and discloses a diazosulfide light-emitting material containing diphenyl phosphine oxide and a preparation method and application thereof. The preparation method includes the steps that benzene, thiophene, carbazole, fluorene, anthracene and pyrene or bromide of pyridine are used as reaction raw materials, and boric acid ester substituted by diphenylphosphine radicals or an intermediate substituted by tributyltin is obtained through a two-step reaction; then the intermediate is reacted with 4,7-dibromo benzothiadiazole or 4,7-bis(5-bromothiophene-2-base)-2,1,3 diazosulfide, and thus a precursor containing diphenylphosphine is obtained; at last, the diazosulfide light-emitting material containing the diphenyl phosphine oxide is obtained through oxidation by an oxidizing agent. The light-emitting material has a good electron injection and transmission property, the light-emitting material of light-emitting colors including red, green, blue and the like can be prepared, and great application prospects are achieved on the aspects of electroluminescent display, illumination 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 field of high-efficiency organic light-emitting materials and organic light-emitting diodes (OrganicLight-EmittingDiode, 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 mo...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F9/6558C07F9/6541H01L51/54
Inventor 李远武颖
Owner SOUTH CHINA UNIV OF TECH
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