Electro-phosphorescence polymer containing (alkyl-substituted-)S,S- dioxo-dibenzothiophene unit and application thereof

A dibenzothiophene and polymer technology, applied in the application field of electrophosphorescent polymers and preparation of light-emitting devices, can solve problems such as reduction, achieve broad application prospects, good stability, and improve the balance of injection and transmission

Inactive Publication Date: 2012-04-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, bandgap and triplet energy levels are often reduced due to intramolecular charge transfer
Therefore, the development of highly efficient phosphorescent polymer materials with bipolarity still faces great challenges.

Method used

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  • Electro-phosphorescence polymer containing (alkyl-substituted-)S,S- dioxo-dibenzothiophene unit and application thereof
  • Electro-phosphorescence polymer containing (alkyl-substituted-)S,S- dioxo-dibenzothiophene unit and application thereof
  • Electro-phosphorescence polymer containing (alkyl-substituted-)S,S- dioxo-dibenzothiophene unit and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: 3, the preparation of 7-dibromo-S, S-dioxy-dibenzothiophene

[0057] 1)

[0058]

[0059] In a 150ml round bottom flask, add dibenzothiophene (9.2g, 50mmol), acetic acid (100ml), 35% concentration of hydrogen peroxide (30mL), and then react under reflux for 6 hours. After the reaction, the reactant was poured into water, filtered, and washed several times with methanol. After drying, it was recrystallized with ethanol to obtain colorless needle crystals, 9.7 g, yield: 90%.

[0060] 2)

[0061]

[0062] In a 100ml single-necked bottle, add S, S-dioxy-dibenzothiophene (5.4g, 25mmol), concentrated sulfuric acid (50ml), slowly add bromosuccinimide (11.1ml, 62.5mmol), room temperature Under reaction for 24 hours. 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 adjusted to be neutral, and the insoluble matter was filtered out, washed with water and dried, and then re...

Embodiment 2

[0063] Example 2: 2,8-dioctyl-3,7-diboronate-S, the preparation of S-dioxo-dibenzothiophene 1)

[0064]

[0065] In a 100ml three-necked flask, add dibenzothiophene (5.5g, 30mmol) and iron powder (0.084g, 1.5mmol) and dissolve in 30mL of chloroform, avoid light, add 3.1mL of liquid bromine at 0-5°C, Reaction 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%.

[0066] 2)

[0067]

[0068] In a 100 ml three-necked flask, add 2,8-dibromo-dibenzothiophene (6.48g, 20mmol), Ni(dppp)Cl 2 (1.08g, 0.2mmol), anhydrous tetrahydrofuran (200mL), protected from light, 10 ℃ dropwise added C 8 h 17 MgBr in diethyl ether (45 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 Grignar...

Embodiment 4

[0079] Example 4: Preparation of 2,7-diboronate-9,9-di-n-octylfluorene

[0080] 1)

[0081]

[0082] In a 250 ml three-necked flask, add fluorene (16.6 g, 100 mmol), iron powder (2.8 g, 5 mmol), and 100 ml of chloroform. After cooling in an ice-water bath, 35 ml of bromine (35.2 g, 220 mmol) / chloroform mixed solution was added dropwise. The temperature in the bottle does not exceed 5°C during the dropwise addition. After the reaction was completed, it was filtered and recrystallized from chloroform to obtain 26.9 g of white crystals with a yield of 83%.

[0083] 2)

[0084]

[0085] Add 2,7-dibromofluorene (9.7g, 30mmol), benzyltriethylammonium chloride (0.07g, 0.3mmol), dimethyl sulfoxide 90mL, 45mL sodium hydroxide aqueous solution (50mL) into a 100mL three-necked flask %). Stir vigorously at room temperature to form a suspension. 1-Bromo-n-octane (12.5 g, 65 mmol) was slowly added dropwise, and after stirring was continued for 3 hours, it was extracted with di...

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PUM

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Abstract

The invention relates to an electro-phosphorescence polymer containing an (alkyl-substituted-)S,S-dioxo-dibenzothiophene unit and application thereof. In the electro-phosphorescence polymer, the (alkyl-substituted-)S,S-dioxo-dibenzothiophene unit is introduced into an electro-phosphorescence polymer chain, and a phosphorescence unit is respectively arranged on the main chain, the side chain or the branched chain of the polymer. The injection/ transmission balance of a hole/ electron is improved, the triplet state energy level of a main body is not obviously changed, and therefore the phosphorescence polymer has higher electroluminescence efficiency. The polymer of the series has the advantages of good stability, solubility, luminescent capability and the like, is suitable for solution processing, such as solution spin coating, ink-jet printing and the like, and has a wide application prospect in the fields of organic photovoltaic materials and devices.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, in particular to a class of electrophosphorescent polymers containing (alkyl-substituted-)S,S-dioxy-dibenzothiophene units and their application in the preparation of light-emitting devices. Background technique [0002] In the past two decades, since phosphorescent materials can simultaneously utilize singlet and triplet excitons to emit light, which has the remarkable advantage of having an internal quantum efficiency close to 100%, new and efficient phosphorescent materials have received extensive attention. In addition, because the polymer material system can use solution spin coating, inkjet printing and other processing methods, it has great potential to reduce production costs, and has become a research hotspot. In order to obtain high-efficiency electrophosphorescent devices, phosphorescent emitters are usually physically or chemically dispersed in wide-bandgap polymer hos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/54
Inventor 杨伟何锐峰张斌郭婷刘杰余磊曹镛
Owner SOUTH CHINA UNIV OF TECH
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