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Light emitting tetraphenylene derivatives, its method for preparation and light emitting device using the same derivatives

A technology of light-emitting device and organic light-emitting device, which is applied in the direction of electroluminescent light source, light-emitting material, electric solid device, etc.

Active Publication Date: 2013-01-02
THE HONG KONG UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But these approaches have had only limited success

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  • Light emitting tetraphenylene derivatives, its method for preparation and light emitting device using the same derivatives
  • Light emitting tetraphenylene derivatives, its method for preparation and light emitting device using the same derivatives
  • Light emitting tetraphenylene derivatives, its method for preparation and light emitting device using the same derivatives

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Experimental program
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preparation example Construction

[0108] The preparation methods of these materials or molecules are simple, and all materials can be obtained in high yields as shown below. All these dye molecules have high thermal stability due to the presence of a large number of aromatic rings in the structure. These molecules fluoresce strongly in the solid state. The electroluminescence of these molecules has shown excellent results and thus can be used in organic light-emitting diodes.

[0109] In one aspect of the present invention, a luminescent material such as a dye molecule is provided, which comprises one or more tetraphenylethylene derivatives having the structural formula of compound 29 in the following scheme 1, and a preparation method of the luminescent material. Among them, R 1 , R 2 , R 3 , R 4 Each is independently selected from H and any organic or organometallic group. These materials have high solid-state quantum efficiency and thermal stability.

[0110] Schema 1

[0111]

[0112] In one emb...

example 1

[0215]

[0216] Compound 19 (1.0mmol), 1-bromopyrene (1.1mmol), Pd(PPh 3 ) 4 (0.05mmol) and potassium carbonate (4.0mmol) was dissolved in 100mL of toluene / ethanol / water (volume ratio 8:1:1), and heated to reflux for 24 hours under nitrogen protection. After filtration and evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane / dichloromethane or ethyl acetate as eluent.

[0217] Characterization data: white solid; 63% yield; m.p.: 303°C. 1 H NMR (300MHz, CD 2 Cl 2 ), δ(TMS,ppm):8.21–8.16(m,3H),8.11–7.93(m,6H),7.37(d,2H,J=8.7Hz),7.22–7.08(m,17). 13 C NMR (75MHz, CD 2 Cl 2 ),δ(TMS,ppm):144.5,144.4,144.3,143.4,142.1,141.4,139.8,138.3,132.2,131.7,131.2,130.6,129.1,128.4,128.2,128.1,128.0,127.2,1126.0,7, ,125.6,125.4,125.3.MS(MALDI-TOF):m / z532.2513(M + , calculated value 532.2191). Elemental analysis: C 42 h 28 Calculated value: C, 94.70; H, 5.30. Found value: C, 94.64; H, 5.29.

example 2

[0219]

[0220] Compound 19 (1.0mmol), 9-bromoanthracene (1.1mmol), Pd(PPh 3 ) 4 (0.05mmol) and potassium carbonate (4.0mmol) were dissolved in 100ml of toluene / ethanol / water (volume ratio 8:1:1), heated to reflux under nitrogen protection for 24 hours. After filtration and evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane / dichloromethane or ethyl acetate as eluent.

[0221] Characterization data: White solid; Yield: 69%. m.p.: 301°C. 1 H NMR (300MHz, CD 2Cl 2 ),δ(TMS,ppm):8.45(s,1H),8.03(d,2H,J=8.4Hz),7.59(d,2H,J=8.7Hz),7.48-7.43(m,2H),7.38 -7.33(m,2H),7.25-7.13(M,19H). 13 C NMR (75MHz, CD 2 Cl 2 ), δ (TMS, ppm): 144.6, 144.4, 144.2, 143.9, 142.3, 137.6, 137.5, 132.2, 132.1, 132.03, 132.00, 131.9, 131.2, 130.8, 129.0, 128.51, 128.45, 128.4, 127 ,126.0,125.9.MS(MALDI-TOF):m / z 508.2436(M + , calculated value 508.2191). Elemental analysis: C 40 h 28 Calculated value: C, 94.45; H, 5.55. Found value: C, 94.14; H,...

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Abstract

Provided are a light emitting material comprising one or more tetraphenylethene (TPE) derivatives of formula (1a) with high thermal stability and high solid state quantum yield efficiency, and an electroluminescent or light emitting device such as OLED comprising the same TPE derivatives and a method of preparing the same.

Description

technical field [0001] The invention relates to a luminescent material and the application of the material in a luminescent device capable of converting electrical energy into light energy. In particular, the present invention relates to light-emitting materials comprising tetraphenylethylene derivatives and their use in light-emitting devices, such as organic light-emitting diodes (OLEDs). Background technique [0002] The synthesis of luminescent materials with high luminous efficiency has always been the focus of scientists. The development of new light-emitting materials often promotes optoelectronic science, such as the progress of organic light-emitting diodes (OLEDs), and people are eager to apply this type of optoelectronic materials in the optoelectronic industry (Chem. Rev. 2007, 107, 1011, Nature 1998, 395, 151). [0003] about a century ago, and Kasper et al. found that the fluorescence of pyrene decreased with the increase of solution concentration. Soon, it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
CPCC09K2211/1011C07D217/02H01L51/0072C07D417/14C09K2211/1092C09K2211/1007C09K2211/1029C07D209/86H05B33/14H01L51/0054H01L51/0059H01L51/0058H01L51/0068C07D285/10C09K2211/1051C09K11/06H10K85/622H10K85/655H10K85/631H10K85/626H10K85/6572
Inventor 唐本忠赵祖金詹嘉慧林荣业陈树明郭海成
Owner THE HONG KONG UNIV OF SCI & TECH
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