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Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof

A dibenzothiophene and alkyl technology, applied in the field of photoelectric materials, can solve the problems of poor solubility and limited application, and achieve the effects of low price, improved solubility, increased band gap and triplet energy level

Active Publication Date: 2010-05-26
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor solubility of S, S-dioxy-dibenzothiophene units, it is difficult to obtain polymers with high S, S-dioxy-dibenzothiophene unit content, and high-efficiency 3,7-substituted The polymer of -S, S-dioxy-dibenzothiophene unit emits sky blue light, which is slightly insufficient as a full-color display material
From the perspective of chemical synthesis, S,S-dioxo-dibenzothiophene is not as easy to modify at the C-9 or N-9 position as fluorene or carbazole, which greatly limits its application in optoelectronic materials

Method used

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  • Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof
  • Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof
  • Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Preparation of 2,8-dioctyl-3,7-dibromo-S, S-dioxo-dibenzothiophene

[0055] 1)

[0056]

[0057] Dissolve dibenzothiophene (5g, 27.1mmol) and 0.1g iron powder in 30mL chloroform, avoid light, add 3.1mL liquid bromine at 0-5°C, and react at room temperature for 20h. Add saturated NaHSO 3 The excess bromine was removed by aqueous solution, and a pale yellow solid was obtained by filtration, washed twice with methanol, and recrystallized from chloroform to obtain a white solid. Yield: 80%. 1 H NMR (300MHz, CDCl 3 ) δ (ppm): 7.58 (m, 2H), 7.71 (m, 2H), 8.24 (m, 2H). Elemental analysis results. (%): C 12 h 6 S, calculated: C, 42.14; H, 1.77; S, 9.37; tested: C, 42.16; H, 1.83; S, 9.31.

[0058] 2)

[0059]

[0060] 2,8-dibromo-dibenzothiophene (6.48g, 20mmol) and 1g Ni(dppp)Cl 2 Dissolve in 200mL anhydrous tetrahydrofuran, avoid light, add the pre-prepared C 8 h 17 MgBr in diethyl ether (45 mmol). After the dropwise addition was completed, remove...

Embodiment 2

[0067] Example 2: Preparation of 2-octyl-3,7-dibromo-S, S-dioxy-dibenzothiophene

[0068] 1)

[0069]

[0070] Dissolve dibenzothiophene (10g, 54.2mmol) and 0.1g iron powder in 50mL of chloroform, avoid light, add liquid bromine (8.6g, 54.2mmol) at 0-5°C, and react at room temperature for 40h. Add saturated NaHSO 3 The excess bromine was removed in aqueous solution, filtered to give a pale yellow solid, and washed twice with methanol to give a white solid. Yield: 50%.

[0071] 2)

[0072]

[0073] 2-Bromo-dibenzothiophene (5.26g, 20mmol) and 1g Ni(dppp)Cl 2 Dissolve in 200mL anhydrous tetrahydrofuran, avoid light, add the prepared C dropwise below 10°C 8 h 17 MgBr ether solution (22 mmol). After the dropwise addition was completed, remove the ice bath, react at room temperature for 2 h, and use saturated NH 4 Cl to remove excess Grignard reagent, extracted with dichloromethane, and dried over magnesium sulfate. Carry out column chromatography with petroleum ethe...

Embodiment 3

[0080] Example 3: Preparation of 3,7-dioctyl-2,8-dibromo-S, S-dioxo-dibenzothiophene

[0081] 1)

[0082]

[0083] In a 150ml round bottom flask, biphenyl (5g, 32.5mmol) was dissolved in 80ml of methylene chloride, bromosuccinimide (NBS) (5.78g, 32.5mmol) was added at room temperature, and then reacted at room temperature 48 hours. After the reaction, the reactant was poured into water, extracted with dichloromethane, and washed with water several times. MgSO 4 Dry, distill off the solvent, and recrystallize from petroleum ether. A white solid was obtained, 5.65 g, yield: 75%.

[0084] 2)

[0085]

[0086]Add 4,4'-dibromobiphenyl (20g, 64.1mmol) to a 150mL three-necked flask, dissolve it in 50mL of chloroform, add chlorosulfonic acid (11.4mL, 171.7mmol) dropwise, and keep the reaction system at 50°C Below, the reaction is 3h. After the reaction was over, the reactant was poured into 500ml of crushed ice, and the ice was melted with NaCO 3 The solution was adjuste...

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Abstract

The invention discloses an alkyl substituted-S,S-dioxo-dibenzothiophene monomer, a preparation method and a polymer thereof. The presence of the strong electron-withdrawing group -SO2- in the alkyl substituted-S,S-dioxo-dibenzothiophene is favorable for improving the electron affinity of molecules, and the introduction of the alkyl greatly improves the dissolubility of the monomer in an organic solvent. The alkyl substituted-S,S-dioxo-dibenzothiophene monomer can form a homopolymer or a copolymer through the polymerization reaction of Suzuki, Stille and Yamamoto. The series of polymers have good dissolubility in the organic solvent, are suitable for processing solution, and have broad application prospects in the fields of organic flat displays, photovoltaic cells and organic field-effect tubes.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, in particular to a preparation method and application of a class of alkyl-substituted-S,S-dioxy-dibenzothiophene monomers and polymers thereof. Background technique [0002] In the past two decades, the organic electronics and optoelectronics industries, including organic / polymer light-emitting diodes, organic field effect transistors, organic solar cells, nonlinear optics, biosensors and lasers, have developed rapidly and are gradually moving toward industrialization. Organic electronic products have the advantages of low price, light weight and portability, which make them have great market potential. Therefore, the development of market-attractive organic electronic products has attracted the attention and investment of many research institutions and scientific research teams in the world. Among them, the development of new efficient and stable materials has undoubtedly becom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/76C08G61/12C09K11/06H01L51/00H01L51/46H01L51/30H10K99/00
CPCY02E10/50Y02E10/549
Inventor 杨伟刘杰应磊彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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