Polymer containing 9,9,10,10-tetraoxy-thianthrene five-element fused-ring unit as well as preparation method and application thereof

A technology of polymer and polymerization reaction, applied in electrical components, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., can solve problems such as reducing LUMO energy level, and achieve the effect of improving electroluminescent performance

Active Publication Date: 2018-05-04
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

However, the current reports have not involved polymers containing 9,9,10,10-tetraoxo-thianthrene five-membered fused ring units, 9,9,10,10-tetraoxo-thianthrene five-membered fused ring Containing at least two argonyl groups, it has stronger charge-absorbing properties than the argonyl group-containing units listed above. When introduced into a polymer, it can further reduce the LUMO energy level, and the five-membered ring structure can further improve9,9, Electron mobility of 10,10-tetraoxo-thianthracene five-membered fused ring unit to improve the luminescent properties and photoelectric conversion efficiency of polymers

Method used

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  • Polymer containing 9,9,10,10-tetraoxy-thianthrene five-element fused-ring unit as well as preparation method and application thereof
  • Polymer containing 9,9,10,10-tetraoxy-thianthrene five-element fused-ring unit as well as preparation method and application thereof
  • Polymer containing 9,9,10,10-tetraoxy-thianthrene five-element fused-ring unit as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Preparation of Compounds 4 and 5

[0064] (1) Preparation of compound 1

[0065] Under nitrogen protection, 2-bromo-7-iodo-9,9-dimethylfluorene (3.99g, 10mmol), 4-bromo-1,2-benzenedithiol (2.21g, 10mmol ), sodium tert-butoxide (4.81g, 50mmol), tris(dibenzylideneacetone)dipalladium (458mg, 0.5mmol), bis(2-diphenylphosphophenyl)ether (269mg, 0.5mmol) and 120mL toluene, heated to 50°C and stirred for 6 hours. After the reaction was completed, the product was extracted with dichloromethane, the organic phase was washed with saturated aqueous sodium chloride solution, the solvent was evaporated under reduced pressure, and the crude product was eluted with a mixed solvent of petroleum ether:dichloromethane=6:1 (v / v) Purified by solvent column chromatography to obtain 3.11 g of white solid with a yield of 63%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0066] (2) Preparation of Compound 2

[0067...

Embodiment 2

[0075] Preparation of Compound M1

[0076] Compound 4 (4.90g, 10mmol) and 150mL tetrahydrofuran and acetic acid mixed solvent (v:v=1:1) were added to a 300mL two-necked flask, and aqueous hydrogen peroxide solution (10mL, 100mmol) was added dropwise, and the reaction was stirred for 12 hours. After the reaction was completed, the product was extracted with dichloromethane, washed with saturated aqueous sodium chloride, and the solvent was removed under reduced pressure. The crude product was used as the eluent column layer with a mixed solvent of petroleum ether:dichloromethane=3:1 (v / v) Analysis and purification gave 4.44 g of white solid with a yield of 80%. 1 H NMR, 13 C NMR, MS and elemental analysis results show that the compound obtained is the target product, and its chemical reaction equation is as follows:

[0077]

Embodiment 3

[0079] Preparation of compound M2

[0080] Add compound 5 (4.90g, 10mmol) and 150mL tetrahydrofuran and acetic acid mixed solvent (v:v=1:1) into a 300mL two-necked flask, slowly add aqueous hydrogen peroxide solution (10mL, 100mmol), and stir for 12 hours. After the reaction was completed, the product was extracted with dichloromethane, washed with saturated aqueous sodium chloride, and the solvent was removed under reduced pressure. The crude product was used as the eluent column layer with a mixed solvent of petroleum ether:dichloromethane=3:1 (v / v) Analysis and purification gave 4.72 g of white solid with a yield of 85%. 1 H NMR, 13 C NMR, MS and elemental analysis results show that the compound obtained is the target product, and its chemical reaction equation is as follows:

[0081]

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Abstract

The invention belongs to the technical field of organic photoelectric and discloses a polymer containing 9,9,10,10-tetraoxy-thianthrene five-element fused-ring unit as well as a preparation method andapplication thereof. The 9,9,10,10-tetraoxy-thianthrene five-element fused-ring unit is a unit with strong electrical absorption and can improve the electron transmission property of the polymer. Through adjusting the copolymer unit proportion, a luminescent spectrum and a band gap can be well adjusted to obtain the polymers with different functions. The five-element parallel-ring structure can further improve the carrier mobility and stability of the polymer. The polymer containing 9,9,10,10-tetraoxy-thianthrene five-element fused-ring unit provided by the invention can be used as the organic photoelectric materials or polymer solar cell materials to prepare into polymer light-emitting diodes and polymer solar cells through a solution processing method.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a polymer containing 9,9,10,10-tetraoxo-thianthrene five-membered condensed ring units and its preparation method and application. 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. Organic solar cell materials started in the 1990s. They are a new type of sustainable renewable low-cost green energy materials, and are easy to prepare large-area flexible batteries, so they have great application potential. [0003] To realize high-efficiency polymer light-emitting diodes, light-emitting materials need to have high fluorescence quantum yield, balanced carrier transport and other characteristics. The commonly used polymer luminescent ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54
CPCC08G61/122C08G2261/95C08G2261/3243C08G2261/3246C08G2261/592C08G2261/514C08G2261/522C08G2261/91C08G2261/1412C08G2261/124C08G2261/3142H10K85/113H10K85/151Y02E10/549
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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