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Poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative with hole transport unit in side chain and preparation method and application of poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative

A technology of dibenzothiophene and hole transport, applied in electrical components, circuits, semiconductor devices, etc., can solve problems such as limited device efficiency and stability, unbalanced carrier transport, and reduced hole transport performance. Achieve the effects of maintaining spectral purity and stability, simplifying the device preparation process, and high fluorescence quantum yield

Inactive Publication Date: 2018-02-27
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reason is that the introduction of S,S-dioxy-dibenzothiophene unit can significantly reduce the HOMO energy level of the polymer and improve the hole injection while reducing the LUMO energy level of the polymer and improving the electron transport performance of the polymer. Potential barrier, which reduces the hole transport performance, makes the carrier transport unbalanced in the polymer, and the device efficiency and stability are limited

Method used

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  • Poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative with hole transport unit in side chain and preparation method and application of poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative
  • Poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative with hole transport unit in side chain and preparation method and application of poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative
  • Poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative with hole transport unit in side chain and preparation method and application of poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of Compound M1

[0045] Add 2,7-dibromofluorenone (3.38g, 10mmol), triphenylamine (7.36 g, 30mmol), methanesulfonic acid (0.96g, 10mmol) and 50ml carbon tetrachloride in a 100ml three-necked flask, under nitrogen conditions , heated to 90°C for 12 hours; the reaction was completed, the product was extracted with dichloromethane, the organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, the solvent was evaporated, and the crude product was used in petroleum ether: dichloromethane=6 : 1 (v / v) mixed solvent was used as eluent for column chromatography to obtain 7.21 g of white solid with a yield of 89%, (mass spectrum: 810.2).

[0046] The chemical reaction equation is as follows:

[0047]

Embodiment 2

[0049] Preparation of Compound M2

[0050] Add 2,7-dibromofluorenone (3.38g, 10mmol), carbazole (7.30g, 30mmol), methanesulfonic acid (0.96g, 10mmol) and 50ml carbon tetrachloride in a 100ml three-necked flask under nitrogen protection conditions , heated to 90°C for 12 hours; the reaction was completed, the product was extracted with dichloromethane, the organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was evaporated, and the crude product was prepared with petroleum ether: dichloromethane= A 6:1 (v / v) mixed solvent was used as the eluent for column chromatography to obtain 6.69 g of a white solid with a yield of 83% (mass spectrum: 806.2).

[0051] The chemical reaction equation is as follows:

[0052]

Embodiment 3

[0054] Preparation of compound M3

[0055] (1) Synthesis of 3,6-di-tert-butyl-9-phenylcarbazole (compound 1): 3,6-di-tert-butylcarbazole (13.97g, 50mmol), bromobenzene (9.42g, 60mmol), sodium tert-butoxide (9.60g, 100mmol), palladium acetate (0.22g, 1mmol), tri-tert-butylphosphine (0.98g, 2mmol) and 80ml toluene; under nitrogen, react at 80°C for 8 hour; after the reaction was completed, the product was extracted with dichloromethane, and the organic phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated, and the crude product was purified by column chromatography using petroleum ether as an eluent to obtain a white solid 15.64 g, 88% yield, (mass spectrum: 355.4).

[0056] (2) Preparation of compound M3: Add 2,7-dibromofluorenone (3.38g, 10mmol), compound 1 (10.67g, 30mmol), methanesulfonic acid (0.96g, 10mmol) and 50ml Carbon tetrachloride was heated to 90° C. to react for 12 hours under nitr...

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Abstract

The invention discloses a poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative with a hole transport unit in a side chain and a preparation method and application of the poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative. The poly(fluorine-co-S,S-dioxo-dibenzothiophene) derivative is prepared from a hole transport unit and an S,S-dioxo-dibenzothiophene through a Suzuki polymerization reaction. As the side chain of poly(fluorine-co-S,S-dioxo-dibenzothiophene) is modified by the hole transport unit, and the side chain is complemented with a main chain with dominant electron transport andis not in direct conjugate with S,S-dioxo-dibenzothiophene with electric absorption, a polymer has the spectrographic purity and the stability because of the electron transport unit and hole transport unit, the device efficiency can be improved, good dissolubility is achieved, and a light emitting layer of a polymer light emitting diode can be prepared.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and in particular relates to a polymer luminescent material that can be used in a single-layer polymer light-emitting diode, a preparation method and application thereof. Background technique [0002] In 1990, the Cavendish Laboratory of the University of Cambridge published the first polymer thin-film electroluminescent device prepared by conjugated polymer PPV, which officially opened the prelude to the research of polymer light-emitting diodes (PLEDs). Compared with small molecule LEDs, polymer LEDs have the following advantages: (1) Large-area thin films can be prepared by solution spin coating, roll-to-roll, etc.; (2) The electronic structure and luminous color of conjugated polymers can be easily obtained through (3) The modification of the conjugated polymer can avoid crystallization, thereby improving the stability of the device. [0003] The PLED device is composed of a c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L33/26
CPCC08G61/126C08G2261/124C08G2261/148C08G2261/3142C08G2261/3243C08G2261/411C08G2261/512C08G2261/95H01L33/26
Inventor 应磊彭沣郭婷杨伟彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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