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A class of polymers containing s,s-dioxo-naphtho[2,1-b]benzothiophene derivative units, preparation method and application

A technology of benzothiophene and derivatives, applied in the field of organic optoelectronics, can solve problems such as limiting the electroluminescence performance of polymer light-emitting materials, and achieve the effects of improving electron injection, improving device performance, and high fluorescence quantum yield

Active Publication Date: 2020-03-24
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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  • A class of polymers containing s,s-dioxo-naphtho[2,1-b]benzothiophene derivative units, preparation method and application
  • A class of polymers containing s,s-dioxo-naphtho[2,1-b]benzothiophene derivative units, preparation method and application
  • A class of polymers containing s,s-dioxo-naphtho[2,1-b]benzothiophene derivative units, preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Preparation of Compound 4

[0047] The synthetic chemical reaction equation of compounds 1-4 is as follows:

[0048]

[0049] (1) Preparation of compound 1

[0050] Under a nitrogen atmosphere, 1-naphthylboronic acid (1.72g, 10mmol), 2-fluoro-4-bromoiodobenzene (3.01g, 10mmol), potassium carbonate (3.45g, 25mmol), tetrakis (tri Phenylphosphine)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 1.63 g of a white solid with a yield of 54%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0051] (2) Preparation of compound 2

[0052] Under a nitrogen at...

Embodiment 2

[0058] Preparation of Compound 8

[0059] Compounds 5, 6, and 7 were successively prepared by a synthesis method similar to Example 1, and compound 8 was finally synthesized as a white solid. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:

[0060]

Embodiment 3

[0062] Preparation of Compound M1

[0063] (1) Preparation of Compound 9

[0064] Under nitrogen protection, compound 15 (5.78g, 10mmol), pinacol diborate (3.81g, 15mmol), [1,1'-bis(diphenylphosphino)ferrocene ] Palladium dichloride (0.49g, 0.5mmol), potassium acetate (3.92g, 40mmol) and 150mL dioxane, heated to 80°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: ethyl acetate = 8:1 (v / v) mixed solvent was used as eluent for column chromatography purification to obtain 4.99 g of white solid with a yield of 80%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0065] (2) Preparation of Compound 10

[0066...

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Abstract

The present invention belongs to the field of organic photoelectric technology, and a polymer and preparation method of the phenye phenolic derivative unit are disclosed in the field of organic photoelectric technology.The chemical structure of the invention polymer is shown below: formula: x 1 , X 2 For the components of each unit, Moore score, satisfy: 0≤x 1 <1, 0 <x 2 ≤1, x 1 +x 2 = 1; n is the duplicate unit, n = 10-1000; y is ‑c (R 1 Cure 2 ‑, R nr 1 R, i si (R 1 Cure 2 ‑, ‑ O ‑, ‑ S ‑, ‑ SO 2 ‑ Or oCO 2 ‑; R 1 For alkyl groups with C1 to 30, cyclotropyl groups with C3 ~ 30, C6 ~ 60 aromatic hydrocarbon base or C3 ~ 60 aromatherapy group; AR is aromatic hydrocarbon base or C3 to 60 aromatic miscellaneous mixedThe cycle.The invention polymer can be applied to the field of organic optoelectronics and prepares the glowing diode light layer of polymer.

Description

technical field [0001] The invention belongs to the field of organic optoelectronic technology, and in particular relates to a polymer containing S,S-dioxo-naphtho[2,1-b]benzothiophene derivative units, a preparation method and an application in the field of organic optoelectronics. Background technique [0002] 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 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/50H01L51/54
CPCC09K11/06C08G61/126C08G2261/95C08G2261/411C08G2261/5222C08G2261/122C08G2261/1412C08G2261/3142C08G2261/3243C09K2211/1416C09K2211/1483C09K2211/1458C09K2211/1466H10K85/151H10K50/11
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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