Thianthrene-containing pentabasic condensed nucleus unit derivative and its synthetic method and application

A synthesis method and derivative technology, applied in the field of five-membered fused ring unit derivatives and their synthesis, can solve the problems of insufficient efficiency of light-emitting materials, and achieve the effects of inhibiting molecular aggregation, conjugation enhancement, and good site selectivity

Inactive Publication Date: 2018-02-23
SOUTH CHINA INST OF COLLABORATIVE INNOVATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The efficiency of current luminescent materials is not high enough. The main material problems that need to be solved include improving thermal stability, fluorescence quantum yield, singlet and triplet energy levels, carrier transport performance, etc., and inhibiting molecular aggregation.

Method used

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  • Thianthrene-containing pentabasic condensed nucleus unit derivative and its synthetic method and application
  • Thianthrene-containing pentabasic condensed nucleus unit derivative and its synthetic method and application
  • Thianthrene-containing pentabasic condensed nucleus unit derivative and its synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of compounds M1 and M2

[0034] (1) Preparation of compound 1

[0035] Under nitrogen protection, add 3-bromo-dibenzothiophene (2.63g, 10mmol), 1,2-benzenedithiol (1.42g, 10mmol), sodium tert-butoxide (4.81g, 50mmol) into a 300ml two-necked flask , tris(dibenzylideneacetone)dipalladium (458mg, 0.5mmol), bis(2-diphenylphosphophenyl)ether (269mg, 0.5mmol) and 150ml toluene, heated to 80°C and stirred for 12 hours. After the reaction was completed, the product was extracted with dichloromethane, the organic phase was washed with saturated aqueous sodium chloride solution, the solvent was evaporated under reduced pressure, and the crude product was eluted with a mixed solvent of petroleum ether:dichloromethane=8:1 (v / v) Purified by solvent column chromatography to obtain 1.85 g of white solid with a yield of 57%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0036] (2) Preparation of Comp...

Embodiment 2

[0047] Synthesis of compounds M3 and M4

[0048] (1) Synthesis of compound 4

[0049] Under nitrogen protection, 2,7-dibromo-9,9-dioctylfluorene (5.48g, 10mmol), 4-(4,4,5,5-tetramethyl-1, 3-dioxo-2-boryl) triphenylamine (2.89g, 10mmol), potassium carbonate (3.45g, 25mmol), tetrakis (triphenylphosphine) palladium (0.58g, 0.5mmol), 12ml deionized water and 120ml of toluene was heated to 80°C for 12 hours. After the reaction is complete, the product is extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and the organic phase solvent is removed, and the crude product is washed with a mixed solvent of petroleum ether:dichloromethane=8:1 (v / v) Purified by column chromatography to obtain 5.51 g of off-white solid with a yield of 77%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0050] (2) Synthesis of compound 5

[0051] Under nitrogen protection, compound 4...

Embodiment 3

[0061] Preparation of Compounds M5 and M6

[0062] (1) Preparation of Compound 8

[0063] Under nitrogen protection, 2-iodo-dibenzofuran (2.94g, 10mmol), 4-bromo-1,2-benzenedithiol (2.21g, 10mmol), sodium tert-butoxide (4.81 g, 50mmol), tris(dibenzylideneacetone)dipalladium (458mg, 0.5mmol), bis(2-diphenylphosphophenyl)ether (269mg, 0.5mmol) and 150ml toluene, heated to 50°C and stirred the reaction 8 hours. After the reaction was completed, the product was extracted with dichloromethane, the organic phase was washed with saturated aqueous sodium chloride solution, the solvent was evaporated under reduced pressure, and the crude product was eluted with a mixed solvent of petroleum ether:dichloromethane=8:1 (v / v) Purified by solvent column chromatography to obtain 2.34 g of white solid with a yield of 60%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0064] (2) Preparation of Compound 9

[0065] Und...

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Abstract

The invention discloses a thianthrene-containing pentabasic condensed nucleus unit derivative and its synthetic method and an application. The thianthrene-containing pentabasic condensed nucleus unitis obtained by performing ring closure on a ternary condensed nucleus unit and benzene derivative after coupling. In the invention, the thianthrene-containing pentabasic condensed nucleus unit is a pentabasic ring combination structure, and is good for improving the output and thermal stability of molecular fluorescence quantum. The thianthrene IN THE thianthrene-containing pentabasic condensed nucleus unit derivative can improve the molecular hole transport performance; besides, the thianthrene has a non-planer structure and can maintain the molecular singlet state and three-line state gradewhile inhibit the molecule piling. The thianthrene-containing pentabasic condensed nucleus unit derivative can be used as an organic lighting or main body material; through evaporation and solution process, the organic lighting diode is prepared.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and specifically relates to a class of five-membered condensed ring unit derivatives and a synthesis method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted extensive attention due to their advantages such as active light emission, high efficiency, low-voltage drive, and easy fabrication of large-area devices. OLED-related research began in the 1950s. In 1987, Deng Qingyun and others from Kodak Corporation of the United States developed an OLED device with a brightness of 1000cd m driven by a 10V DC voltage using a sandwich device structure. -2 , which makes OLED research an epoch-making development. [0003] The OLED device structure includes a cathode, an anode, and an organic layer in the middle. The organic layer generally includes an electron / hole transport layer and a light-emitting layer. Under the action of an ele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/08C07D495/04C07F5/02C07F7/08C09K11/06H01L51/54
CPCC09K11/06C07D339/08C07D495/04C07F5/025C07F7/0816C09K2211/1092C09K2211/1088C09K2211/1096C09K2211/1011C09K2211/1007C09K2211/1014H10K85/615H10K85/631H10K85/6576H10K85/657H10K85/40H10K85/6572
Inventor 应磊彭沣钟知鸣黄飞曹镛
Owner SOUTH CHINA INST OF COLLABORATIVE INNOVATION
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