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9, 9, 10, 10-tetraoxygen-thianthrene-contained water/alcohol-soluble polymer as well as preparation method and application thereof

A polymer, alcohol-soluble technology, used in applications, semiconductor/solid-state device manufacturing, household appliances, etc., can solve the problems of high electron mobility, lower LUMO energy level, etc., achieve simple processing technology, improve electron injection and transmission capabilities , the effect of improving the exciton recombination efficiency

Inactive Publication Date: 2018-02-09
SOUTH CHINA INST OF COLLABORATIVE INNOVATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current reports have not yet involved polymers containing 9,9,10,10-tetraoxo-thianthrene units, which contain two pyranyl groups, and S, Compared with S-dioxy-dibenzothiophene unit, it has stronger electric absorption. It can further reduce the LUMO energy level when introduced into the polymer, while maintaining a high electron mobility. It can be used as an electron transport layer in organic light emitting diode

Method used

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  • 9, 9, 10, 10-tetraoxygen-thianthrene-contained water/alcohol-soluble polymer as well as preparation method and application thereof
  • 9, 9, 10, 10-tetraoxygen-thianthrene-contained water/alcohol-soluble polymer as well as preparation method and application thereof
  • 9, 9, 10, 10-tetraoxygen-thianthrene-contained water/alcohol-soluble polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of compound 3

[0042] (1) Preparation of compound 1

[0043]Under nitrogen protection, 4-bromo-2-iodothiophenol (3.15g, 10mmol), palladium acetate (112mg, 0.5mmol), triphenylphosphine (0.26g, 0.5mmol), tert-butyl Sodium alkoxide (2.88g, 30mmol) and 80ml of anhydrous toluene were heated to 80°C and reacted for 24 hours; after the reaction liquid was cooled, the product was extracted with dichloromethane, and the organic phase was washed three times with saturated saline; the solvent was spin-dried, and the crude product was used Petroleum ether was used as the eluent for column chromatography to obtain 3.18 g of a white solid with a yield of 85%. 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 (3.73g, 10mmol) and 150ml of anhydrous tetrahydrofuran were added to a 300ml two-neck flask, cooled to -78°C, a...

Embodiment 2

[0053] Preparation of compound M1

[0054] Under the protection of nitrogen, add compound 4 (7.08g, 10mmol), diethylamine (3.66g, 50mmol) and 100ml tetrahydrofuran into a 300ml two-necked flask, stir and heat to 70°C for 8 hours; cool the reaction solution, and dichloromethane The product was extracted, washed three times with water, and the solvent in the organic phase was removed by rotary evaporation to obtain a crude product, which was then recrystallized three times with a mixed solvent of ethanol / n-hexane to obtain 4.51 g of a white crystal product with a yield of 65%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product. The chemical reaction equation is as follows:

[0055]

Embodiment 3

[0057] Preparation of compound M2

[0058] Under nitrogen protection, compound 4 (7.08g, 10mmol), diethanolamine (5.26g, 50mmol) and 70ml N,N-dimethylformamide were added to a 150ml two-necked flask, heated to 65°C for 8 hours; The product was extracted with methyl chloride, washed three times with water, and the solvent in the organic phase was removed by rotary evaporation to obtain a crude product, which was recrystallized three times with a mixed solvent of ethanol / n-hexane to obtain 5.36 g of a white powder product with a yield of 71%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product. The chemical reaction equation is as follows:

[0059]

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Abstract

The invention belongs to the technical field of organic photoelectricity, and discloses a 9, 9, 10, 10-tetraoxygen-thianthrene-contained water / alcohol-soluble polymer as well as a preparation method and application thereof. The structure of the polymer is as shown in formula (1), where x is greater than 0 and less than or equal to 0.5, n is a repeated unit and is equal to 10 to 1,000, and R1 is apolar group-containing water / alcohol-soluble side chain. According to the 9, 9, 10, 10-tetraoxygen-thianthrene-contained water / alcohol-soluble polymer, through the introduction of a polar side chain-contained 9, 9, 10, 10-tetraoxygen-thianthrene unit into the polymer, the LUMO energy level of the polymer can be reduced, the electron mobility can be increased, injection and transmission of electrons are facilitated, and the HOMO energy level of the polymer can be reduced at the same time to prevent hole transportation; a strong polar group on a side chain enables the polymer to be dissolved with a strong polar solvent such as water and alcohol, and a uniform thin film is prepared through a solution processing mode, so that solvent orthogonal processing can be realized. The polymer is applied to an electron transmission layer of an organic light emitting diode, and the device efficiency can be improved.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and specifically relates to a water / alcohol-soluble polymer containing 9,9,10,10-tetraoxo-thianthrene, a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes adopt a "sandwich" device structure, which is composed of a cathode, an anode and an organic layer (including an electron transport layer, a light-emitting layer, a hole transport layer, etc.) sandwiched in the middle. The working mechanism of the device is: electrons and holes are separated It is injected from the cathode and anode, and migrates in the functional layer respectively, then electrons and holes form excitons at appropriate positions, the excitons migrate within a certain range, and finally the excitons transition to the ground state to emit light. [0003] High work function metals such as Al and Ag are currently the most commonly used cathode materials for organ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09D165/00C09D11/30C09D11/102H01L51/50H01L51/54H01L51/56
CPCC09D11/102C09D11/30C09D165/00C08G61/122C08G2261/411C08G2261/95C08G2261/3142C08G2261/3241C08G2261/1412C08G2261/1422C08G2261/143C08G2261/1452C08G2261/147C08G2261/122C08G2261/124H10K71/12H10K71/13H10K71/135H10K85/113H10K85/151H10K50/16H10K2101/30
Inventor 应磊彭沣胡黎文黄飞曹镛
Owner SOUTH CHINA INST OF COLLABORATIVE INNOVATION
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