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Rubrene analogue, as well as preparation method and application thereof

A reaction and compound technology, applied in the field of rubrene analogues and their preparation, achieves the effects of good repeatability, high universality, and cheap raw materials

Inactive Publication Date: 2012-10-10
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the method of directly using the structure of rubrene to replace phenyl with other types of aromatic groups (such as thiophene) to prepare rubrene analogues has not been reported.

Method used

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  • Rubrene analogue, as well as preparation method and application thereof
  • Rubrene analogue, as well as preparation method and application thereof
  • Rubrene analogue, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1. Preparation of 5,11-diphenyl-6,12-dithienyltetracene (DPDTTA) represented by formula I

[0038] In a 50mL two-necked flask, add 1,1-diphenyl-3-(2-thienyl)propynyl alcohol (1.45g, 5mmol) represented by formula II, add 30ml of dry solvent toluene, and evacuate with argon. Slightly heat and stir until it is completely dissolved, place the flask in an ice-water bath, add the single electron transfer reagent N,N-diisopropylethylamine (1.75mL, 8.5mmol), and slowly add the electrophile benzenesulfonate dropwise after 5min Acyl chloride (0.85mL, 7.5mmol), reacted at 0°C-5°C for 20min, heated to 110°C for 10h. Cool down to room temperature and finish the reaction. Wash the extraction with ethyl acetate (50mL) and 2M hydrochloric acid solution, dry the organic liquid with anhydrous magnesium sulfate, and purify it with a silica gel column (the eluent is petroleum ether to obtain 273 mg of a red solid ( Yield: 20%).

[0039] The structural characterization data of the...

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Abstract

The invention discloses a rubrene analogue, as well as a preparation method and the application of the rubrene analogue. The compound is shown in the formula I. The synthetic route provided by the invention has the advantages of being simple, high in efficiency, low in environmental pollution, low in price of raw materials and synthesis cost, good in universality and repeatability, etc. The rubrene analogue, as well as a preparation method and the application thereof disclosed by the invention can be widely popularized and applied to synthesizing other rubrene analogues with various aryl substituent groups shown in the formula I.

Description

technical field [0001] The invention relates to a rubrene analogue, a preparation method and application thereof. Background technique [0002] Since doped polyacetylene was found to be conductive in 1977, a wave of organic electronics research and development has been set off. π-conjugation is a common feature of organic electronic materials. In general, fused ring and heterocyclic compounds with large conjugated systems have potential research and application prospects, such as pentacene, copper phthalocyanine, etc. [0003] Polycyclic aromatic compound rubrene, with its high fluorescence quantum efficiency (Φ>0.75) and high hole mobility (>15cm 2 / V.s), have been extensively studied in both organic light-emitting devices (OLEDs) and organic field-effect transistors (OFETs), and have become classic materials in organic electronics. At the same time, rubrene has been widely used in photoluminescence, electroluminescence, chemiluminescence, composite materials and ot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/08C09K11/06H01L51/54
Inventor 张小涛胡文平
Owner INST OF CHEM CHINESE ACAD OF SCI
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