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Five-member parallel-ring phenanthrene unit containing monomers and polymers and preparation methods and application thereof

A polymer and phenanthrene-containing technology, applied in the direction of hydrocarbon production from oxygen-containing organic compounds, chemical instruments and methods, preparation of halogenated hydrocarbons, etc., can solve the problems that limit the electroluminescence performance of polymer light-emitting materials, and achieve strong electron transport Effects of performance, good solubility, high fluorescence quantum yield and carrier mobility

Active Publication Date: 2018-08-21
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

[0004] At present, the commonly used polymer luminescent materials are mostly hole transport type, which limits the electroluminescence performance of polymer luminescent materials.

Method used

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  • Five-member parallel-ring phenanthrene unit containing monomers and polymers and preparation methods and application thereof
  • Five-member parallel-ring phenanthrene unit containing monomers and polymers and preparation methods and application thereof
  • Five-member parallel-ring phenanthrene unit containing monomers and polymers and preparation methods and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the preparation of compound 4

[0052] (1) Preparation of compound 1

[0053] Under nitrogen protection, dissolve 3-bromo-9,10-phenanthrenequinone (2.87g, 10mmol) in 50mL of anhydrous tetrahydrofuran, stir and cool down to -78°C, then slowly add 2mol / L tetrahydrofuran of butylmagnesium bromide dropwise solution (30 mL, 60 mmol). After the dropwise addition was completed, it was naturally raised to room temperature and stirred overnight, and the reaction was quenched with a small amount of water. The product was extracted with dichloromethane after spin-drying THF, washed 3 times with saturated aqueous sodium chloride solution, and the solution in the organic phase was spin-dried to obtain 3.22 g of the product. Yield 80%. The results of MS and elemental analysis showed that the obtained compound was the target product.

[0054] (2) Preparation of Compound 2

[0055] Compound 1 (4.03 g, 10 mmol) was dissolved in 50 mL of acetic acid and 20 mL of trifluo...

Embodiment 2

[0062] Embodiment 2: the preparation of compound M1 and M2

[0063] (1) Preparation of Compound 5

[0064] Under nitrogen protection, methyl o-bromobenzoate (2.15g, 10mmol), pinacol diboronate (3.05g, 12mmol), potassium acetate (3.92g, 40mmol), [1,1'-bis(diphenyl Phosphino)ferrocene]palladium dichloride (0.49g, 0.5mmol) was added into 150mL of dioxane, heated to 85°C for 12 hours. Dioxane was removed by distillation under reduced pressure after the reaction was completed, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and dichloromethane was removed by distillation under reduced pressure, and the crude product was purified with petroleum ether:dichloromethane=3:1 (v / v) mixed solvent was used as eluent and purified by column chromatography to obtain 2.25 g of solid with a yield of 86%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[00...

Embodiment 3

[0075] Embodiment 3: the synthesis of compound 11

[0076] The synthesis of compound 11 is similar to that of Example 1. According to the method of Example 1, the starting material was replaced by 2-bromo-9,10-phenanthrenequinone to prepare compounds 8, 9, 10, 11, 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0077] The chemical reaction equation for the synthesis of compounds 8-11 is as follows:

[0078]

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Abstract

The invention discloses five-member parallel-ring phenanthrene unit containing monomers, five-member parallel-ring phenanthrene unit containing polymers and preparation methods and application thereof. With a phenanthrene unit as a basis, through coupling, ring closing and other reactions, a conjugated structure of a molecule is enlarged, the stability of the molecule is improved and the fluorescence quantum yield is increased. The phenanthrene unit has relatively strong electron transmission performance, and the electron transmission performance is further enhanced after a conjugate plane isenlarged. The unit with a relatively good electron transmission characteristic can compensate for the shortage of the electron mobility of common polymeric luminescent materials and improve the electroluminescent property of the polymeric luminescent materials. The five-member parallel-ring phenanthrene unit containing polymers have relatively high fluorescence quantum yield and carrier mobility,have relatively large potentials as luminescent polymers, and can also achieve different color emission through the adjustment of the polymerization unit content. Such the polymers have very good solubility and can be prepared into large-area films by solution processing methods such as spin coating, ink-jet printing and printing.

Description

technical field [0001] The invention belongs to the field of organic optoelectronics, and specifically relates to a class of monomers and polymers containing phenanthrene-containing five-membered ring units and their preparation methods and applications. Background technique [0002] In 1990, the Cavendish Laboratory of the University of Cambridge first published a polymer thin film electroluminescent device prepared by conjugated polymer PPV, marking the beginning of polymer light-emitting diode research. Compared with evaporation-type small molecule light-emitting diodes, polymer light-emitting diodes have the following advantages: (1) large-area thin films can be prepared by wet processing methods such as solution spin coating and roll-to-roll; (2) conjugated polymer electronics The structure and luminescent color can be adjusted by changing and modifying the chemical structure; (3) The modification of the conjugated polymer can avoid material crystallization, thereby imp...

Claims

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Application Information

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IPC IPC(8): C07C13/62C07C1/20C07C25/22C07C17/12C07D209/80C07D333/50C08G61/02C08G61/12C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C13/62C07C25/22C07D209/80C07D333/50C08G61/02C08G61/124C08G61/126C07C2603/52C08G2261/95C08G2261/411C08G2261/5222C08G2261/122C08G2261/124C08G2261/1412C08G2261/3241C08G2261/3243C08G2261/3142C09K2211/1458C09K2211/1466C09K2211/1416C09K2211/1483H10K85/111H10K85/113H10K50/11
Inventor 应磊彭沣钟知鸣黄飞曹镛
Owner 东莞伏安光电科技有限公司
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