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Blue oligomer based on dibenzothiophene-S,S-dioxide unit and preparation method and application of blue oligomer

A technology of dioxydibenzothiophene and oligomer, which is applied in the field of blue oligomer and its preparation, can solve the problem of low performance of polymer OLED devices, high price of OLED device products, and limited market competitiveness of OLED products. and other problems, to achieve the effect of good spectral stability, novel structure and good solubility

Inactive Publication Date: 2017-02-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The use of small molecule light-emitting materials to prepare OLEDs requires a vacuum evaporation production process, which makes the price of OLED devices remain high, which greatly limits the market competitiveness of OLED products.
The use of polymer light-emitting materials can realize the preparation of OLED devices by solution processing, which greatly reduces the cost of OLED products. However, due to the problems of polymer purification and material batch repeatability, the performance of polymer OLED devices is significantly lower than that of small molecule OLEDs. device

Method used

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  • Blue oligomer based on dibenzothiophene-S,S-dioxide unit and preparation method and application of blue oligomer
  • Blue oligomer based on dibenzothiophene-S,S-dioxide unit and preparation method and application of blue oligomer
  • Blue oligomer based on dibenzothiophene-S,S-dioxide unit and preparation method and application of blue oligomer

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Preparation of 2,7-dibromofluorene

[0047] In a 1000mL three-necked flask, add fluorene (60g, 301mmol), iron powder (0.84g, 15mmol) and chloroform (400mL), ice-bath to 5°C, under dark conditions, liquid bromine (35mL, 753mmol) and 115mL The mixture of chloroform was slowly added dropwise into the reaction solution, and after the dropwise addition was completed, the mixture was vigorously stirred at room temperature (stirring speed was 800 rpm) and reacted for 12 hours. Add 200 mL of a saturated aqueous solution of sodium bisulfite to the reaction flask to quench the reaction. The reaction mixture was suction filtered, and the filter residue was washed three times successively with saturated aqueous sodium bisulfite solution, water and ethanol. After the filter residue was dried, it was washed with CHCl 3 Purification was carried out by recrystallization to obtain 77.8 g of white crystals, yield: 80%. 1 H NMR (300MHz, CDCl 3 ) (ppm): 7.54 (d, 2H), 7.44 (d, 2H), 7.31 ...

Embodiment 2

[0050] Preparation of 2,7-dibromo-9,9-dioctylfluorene

[0051]Under the protection of argon, in a 500mL three-necked flask, add 2,7-dibromofluorene (32.4g, 100mmol) and dimethyl sulfoxide (250mL), under vigorous stirring (stirring speed is 800rpm), add tetrabutyl Ammonium bromide (1.61g, 5mmol), and then sodium hydroxide (40g, 1mol) 50wt% aqueous solution was slowly added dropwise, and the reaction was completed for 2 hours, and 1-bromooctane (57.9g, 0.3mol) was injected in one go. After continuing to react for 10 hours, stop the reaction, pour the reaction solution into water, add aqueous hydrochloric acid for neutralization, extract with dichloromethane, wash 7 times with saturated brine, dry, spin dry the solvent, and use column chromatography to analyze the crude The product was purified by using petroleum ether as an eluent to obtain 43.8 g of a white solid with a yield of about 80%. 1 H NMR (300MHz, CDCl 3 )(ppm): 7.53(d, 2H), 7.46(d, 2H), 7.41(d, 2H), 1.94(m, 4H), 1.2...

Embodiment 3

[0054] Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene

[0055] Under the protection of argon, add 2,7-dibromo-9,9-dioctylfluorene (21.9g, 40mmol) and 250mL of anhydrous tetrahydrofuran into a 500mL three-neck flask, and cool the reaction liquid to -78°C with liquid nitrogen. ℃, slowly drop n-butyllithium in n-hexane solution (48mL, 2.5M, 120mmol), keep stirring at -78℃ for 2 hours, inject 2-isopropyl-4,4,5,5-tetra Methyl-1,3,2-dioxaborane (26g, 140mmol), let it rise to room temperature naturally, and continue to react for 20h. Add ammonium chloride aqueous solution to quench the reaction, rotary evaporate most of the solvent, the reaction mixture is poured into water, and extracted with dichloromethane, washed 5 times, the organic phase is separated, dried, and after filtering and spin-drying the solvent, the column chromatography method ( Eluent: petroleum ether) was used to purify the crude product, and 19.8 g of white solid was obta...

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Abstract

The invention discloses a blue oligomer based on a dibenzothiophene-S,S-dioxide unit and a preparation method and application of the blue oligomer. The blue oligomer is mainly characterized by comprising a fluorene structure unit and the dibenzothiophene-S,S-dioxide structure unit. The preparation method mainly comprises the step of preparation of the blue oligomer based on the dibenzothiophene-S,S-dioxide unit. Due to the fact that the electroluminescence efficiency and the spectral stability are improved by introducing the dibenzothiophene-S,S-dioxide structure unit into the oligomer, the novel oligomer blue-light emitting material is obtained. According to the obtained blue oligomer based on the dibenzothiophene-S,S-dioxide unit, an electroluminescence device prepared through film formation of a solution processing method is high in efficiency, good in spectral stability and suitable for being adopted as a light-emitting layer of a light-emitting diode and a flat-panel displayer.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting diode blue light materials, in particular to a blue oligomer based on S,S-dioxodibenzothiophene units, a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted extensive attention from both industry and academia due to their potential applications in large-area flat panel displays. Red, green and blue materials are the three primary color materials necessary for full-color display. In the past two decades, although organic electroluminescent materials have made great progress, only green light materials meet the requirements of commercialization in terms of brightness, efficiency and lifespan, while red and blue light materials still have significant requirements for commercialization. insufficient. This requires us to continue to explore new blue light polymers so that their performance indicators can meet pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/76C07F7/08C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D333/76C07F7/0812C09K2211/1011C09K2211/1092C09K2211/1096H10K85/6576H10K85/40H10K50/11
Inventor 郭婷杨伟应磊胡黎文曹镛
Owner SOUTH CHINA UNIV OF TECH
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