Polymer containing 9,9,10,10-tetraoxo-thianthracene seven-membered fused ring unit, preparation method and application thereof

A technology of polymer and thianthrene, which is applied in the fields of electrical components, semiconductor/solid-state device manufacturing, and electric solid-state devices, etc., can solve the problems of limiting the electroluminescence performance of polymer light-emitting materials, and achieve the improvement of electron transport performance and electron injection ability, the effect of improving carrier mobility and stability

Active Publication Date: 2019-12-03
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the commonly used polymer light-emitting materials are mostly hole-transport type, that is, the hole injection and transport performance is stronger than that of electrons, which limits the electroluminescence performance of polymer light-emitting materials.

Method used

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  • Polymer containing 9,9,10,10-tetraoxo-thianthracene seven-membered fused ring unit, preparation method and application thereof
  • Polymer containing 9,9,10,10-tetraoxo-thianthracene seven-membered fused ring unit, preparation method and application thereof
  • Polymer containing 9,9,10,10-tetraoxo-thianthracene seven-membered fused ring unit, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of compound M1

[0042] (1) Preparation of compound 1

[0043] Under nitrogen protection, add 4-bromo-2 iodothiophenol (3.15g, 10mmol), palladium acetate (0.13mg, 0.5mmol), triphenylphosphine (0.26g, 1mmol) and tert-butyl Sodium alkoxide (3.85g, 40mmol) and 60mL of anhydrous toluene were heated to 80°C for 24 hours. After the reaction solution was cooled, the product was extracted with dichloromethane, and the organic phase was washed three times with saturated brine. The solvent was spin-dried, and the crude product was purified by column chromatography using petroleum ether as an eluent to obtain 2.69 g of a white solid with a yield of 72%. 1 HNMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0044] (2) Preparation of Compound 2

[0045] Under nitrogen protection, compound 1 (3.74g, 10mmol), pinacol diborate (6.35g, 25mmol), [1,1'-bis(diphenylphosphino)ferrocene ] Pall...

Embodiment 2

[0056] Embodiment 2: the preparation of compound M2

[0057] (1) Preparation of Compound 6

[0058] Under nitrogen atmosphere, compound 2 (4.68g, 10mmol), 5-bromo-2-iodonitrobenzene (9.84g, 30mmol), potassium carbonate (3.45g, 25mmol), tetrakis(triphenyl Phosphine)palladium (0.58g, 0.5mmol), 12mL of deionized water and 50mL of toluene were heated to 80°C for 12 hours. After the reaction was completed, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and the organic phase solvent was removed, and the crude product was purified by column chromatography using petroleum ether as eluent to obtain 4.07 g of a yellow solid with a yield of 66%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0059] (2) Preparation of Compound 7

[0060] Under nitrogen protection, compound 6 (6.16 g, 10 mmol) and 50 mL of triethyl phosphite were added into a 150 ...

Embodiment 3

[0067] Embodiment 3: the preparation of compound M3

[0068] (1) Preparation of Compound 9

[0069] Under a nitrogen atmosphere, compound 2 (4.68g, 10mmol), 2-iodonitrobenzene (7.47g, 30mmol), potassium carbonate (3.45g, 25mmol), tetrakis(triphenylphosphine) palladium were added to a 150mL two-necked flask (0.58g, 0.5mmol), 12mL deionized water and 50mL toluene, heated to 80°C for 12 hours. After the reaction was completed, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and the organic phase solvent was removed, and the crude product was purified by column chromatography using petroleum ether as eluent to obtain 3.44 g of a yellow solid with a yield of 75%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0070] (2) Preparation of Compound 10

[0071] Under nitrogen protection, compound 9 (4.59 g, 10 mmol) and 50 mL of triethyl phosphit...

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Abstract

The invention discloses a polymer containing 9,9,10,10-tetraoxo-thianthrene seven-membered condensed ring unit, a preparation method and an application thereof. The general formula of the polymer structure containing 9,9,10,10-tetraoxo-thianthrene seven-membered fused ring unit is as follows, where x 1 、x 2 is the mole fraction of component unit components, satisfying: 0≤x 1 <1, 0<x 2 ≤1,x 1 +x 2 =1; n is a repeating unit, n=10-1000. The polymer has good thermal stability and high fluorescence quantum yield, and the existence of the sulfone unit can also improve the electron transport performance of the polymer. By adjusting the proportion of copolymerized units, the luminescence spectrum of the polymer can be adjusted, and polymers with different colors of luminescence can be obtained. This kind of polymer containing 9,9,10,10-tetraoxo-thianthrene seven-membered condensed ring unit can be used as an organic light-emitting material, and a polymer light-emitting diode can be prepared by a solution processing method.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and specifically relates to a polymer containing 9,9,10,10-tetraoxo-thianthracene seven-membered condensed ring unit, a preparation method and application thereof. Background technique [0002] Organic / polymer light-emitting diodes (O / PLEDs) are a class of light-emitting diodes based on organic small molecules and polymer materials. It has broad application prospects in the field of organic flat panel display and white light lighting. The research on polymer light-emitting diodes (PLEDs) began in 1990, marked by the publication of the first polymer thin-film electroluminescent device prepared by conjugated polymer PPV at the Cavendish Laboratory of the University of Cambridge. 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 luminou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54
CPCC08G61/122C08G2261/95C08G2261/344C08G2261/411C08G2261/5222C08G2261/512C08G2261/122C08G2261/1412C08G2261/3142H10K85/151H10K50/11
Inventor 应磊彭沣黄飞曹镛
Owner 东莞伏安光电科技有限公司
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