Sulfur-containing quaternary condensed ring unit and its derivative and preparation method and application thereof

A technology of derivatives and fused rings, which is applied in the field of sulfur-containing quaternary fused ring units and their derivatives and preparations, can solve the problems of insufficient efficiency of luminescent materials, and achieve improved electroluminescence efficiency, inhibition of molecular aggregation, and strong molecular rigidity Effect

Active Publication Date: 2018-08-03
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Sulfur-containing quaternary condensed ring unit and its derivative and preparation method and application thereof
  • Sulfur-containing quaternary condensed ring unit and its derivative and preparation method and application thereof
  • Sulfur-containing quaternary condensed ring unit and its derivative and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of compound M1

[0045] (1) Preparation of compound 1

[0046] Under nitrogen protection, 1-iodo-naphthalene (2.54g, 10mmol), methyl thiosalicylate (1.68g, 10mmol), sodium tert-butoxide (4.81g, 50mmol), tris(di Benzylideneacetone) dipalladium (458mg, 0.5mmol), bis(2-diphenylphosphophenyl) ether (269mg, 0.5mmol) and 90mL toluene were 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=4:1 (v / v) Purified by solvent column chromatography to obtain 2.65 g of white solid with a yield of 90%. 1 HNMR, 13 The results of C NMR, MS and elemental analysis showed that the obtained compound was the target product.

[0047] (2) Preparation of compound 2

[0048] Und...

Embodiment 2

[0053] Embodiment 2: the preparation of compound M2

[0054] Under nitrogen protection, compound M1 (2.76g, 10mmol) and 90mL of chloroform were added to a 150mL two-necked flask. Hour. After the reaction was completed, the reaction was quenched with an appropriate amount of sodium bisulfite, the product was extracted with dichloromethane, the organic phase was washed with a saturated aqueous sodium chloride solution, the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography using petroleum ether as an eluent. 3.34 g of white solid was obtained, the yield was 77%. 1 H NMR, 13 The results of C NMR, MS and elemental analysis showed that the obtained compound was the target product. Its chemical reaction equation is as follows:

[0055]

Embodiment 3

[0056] Embodiment 3: the preparation of compound M3

[0057] The chemical reaction equation is as follows:

[0058]

[0059] (1) Preparation of Compound 3

[0060] Under nitrogen protection, 1-bromo-4-iodo-naphthalene (3.33g, 10mmol), 4-bromo-1,2-benzenedithiol (2.21g, 10mmol), sodium tert-butoxide ( 4.81g, 50mmol), tris(dibenzylideneacetone)dipalladium (458mg, 0.5mmol), bis(2-diphenylphosphophenyl)ether (269mg, 0.5mmol) and 90mL toluene, heated to 50°C and stirred React for 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 purified by column chromatography using petroleum ether as the eluent to obtain 2.34 g of a white solid, with a yield of 55%. . 1 H NMR, 13 The results of C NMR, MS and elemental analysis showed that the obtained compound was the target product.

[0061] (...

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Abstract

The invention belongs to the technical field of organic optoelectronics, and discloses a sulfur-containing quaternary condensed ring unit and its derivative and a preparation method and an applicationthereof. The sulfur-containing quaternary condensed ring unit has a chemical structural formula shown as the specification, and in the structural formula, X is -C(R1)2-, -NR1-, -Si(R1)2-, -O-, -S-, -(SO)O- or -(CO)O-; R1 is phenyl or C1-4 alkyl; and Y is H, Br or I. The invention also provides the derivative of the sulfur-containing quaternary condensed ring unit. The sulfur-containing quaternarycondensed ring unit and its derivative can be used in an organic light-emitting diode, have a large condensed ring structure, and can increase the thermostability of molecules, and the thermal decomposition temperature exceeds 350 DEG C; the molecule energy grade and band gap can be increased, and molecule aggregation can be inhibited; the sulfur-containing quaternary condensed ring unit has highfluorescence quantum yield, and is in favor of increasing electroluminescent efficiency, conjugation is enhanced, the carrier transmission performance is increased, and the sulfur-containing quaternary condensed ring unit is in favor of increasing the equipment performance.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and in particular relates to a kind of sulfur-containing four-membered condensed ring unit and its derivatives, preparation method and application. 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 a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/04C07D339/08C07D409/14C09K11/06H01L51/54
CPCC09K11/06C07D335/04C07D339/08C07D409/14C09K2211/1092C09K2211/1088C09K2211/1014C09K2211/1011C09K2211/1007H10K85/636H10K85/626H10K85/633H10K85/6576H10K85/6574
Inventor 应磊彭沣郭婷钟知鸣胡黎文
Owner 东莞伏安光电科技有限公司
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