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Terpyridine derivative and preparation method thereof, and applications of terpyridine derivative in organic electroluminescent devices

A technology of terpyridine and its derivatives, which is applied in the preparation method and application, can solve the problems such as difficult to precisely control the doping and increase the complexity of the device, and achieve the effects of low driving voltage, low efficiency roll-off, and high fluorescence quantum yield

Inactive Publication Date: 2019-05-07
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the thermal evaporation of the doped light-emitting layer not only increases the complexity of the device, but it is not easy to precisely control the doping ratio

Method used

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  • Terpyridine derivative and preparation method thereof, and applications of terpyridine derivative in organic electroluminescent devices
  • Terpyridine derivative and preparation method thereof, and applications of terpyridine derivative in organic electroluminescent devices
  • Terpyridine derivative and preparation method thereof, and applications of terpyridine derivative in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of Example 1: Under argon protection, 0.78 g of 4-bromophenyl terpyridine derivatives (intermediate 1), 0.38 g of phenoxazine, and 15 mg of palladium acetate were added to a 100 mL two-port reactor equipped with a reflux tube. 0.5 mL of a toluene solution of 10% tri-tert-butylphosphine was added, and 60 mL of toluene was added. The resulting solution was heated to 90°C and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and dichloromethane and dried over anhydrous sodium sulfate. After distilling off the organic liquid phase, the product was purified by column chromatography with dichloromethane and methanol. After drying, 800 mg of yellow-green powder was obtained, with a yield of 81.5%.

[0032] Product characterization: 1 H NMR (400MHz, DMSO-d 6 )δ9.60–9.59(m,2H),8.80–8.75(m,2H),8.75–8.72(m,2H),8.52(s,2H),8.45(d,J=8.5Hz,2H),7.67 (d,J=8.5Hz,...

Embodiment 2

[0036] Synthesis of Example 2: Under argon protection, 0.78 g of 4-bromophenyl terpyridine derivatives (intermediate 2), 0.38 g of phenoxazine, and 15 mg of palladium acetate were added to a 100 mL two-port reactor equipped with a reflux tube. 0.5 mL of a toluene solution of 10% tri-tert-butylphosphine was added, and 60 mL of toluene was added. The resulting solution was heated to 90°C and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and dichloromethane and dried over anhydrous sodium sulfate. After distilling off the organic liquid phase, the product was purified by column chromatography with dichloromethane and methanol. After drying, 820 mg of yellow powder was obtained, with a yield of 83.5%.

[0037] Product Characterization: 1 H NMR (600MHz, DMSO-d 6)δ9.75(s,4H),9.30(s,2H),8.63(s,2H),8.42(d,J=8.5Hz,2H),7.65(d,J=8.4Hz,2H),6.76– 6.74(m,2H),6.69–6.66(m,4...

Embodiment 3

[0041] Synthesis of Example 3: Under argon protection, 0.78 g of 4-bromophenyl terpyridine derivative (intermediate 3), 0.38 g of phenoxazine, and 15 mg of palladium acetate were added to a 100 mL two-port reactor equipped with a reflux tube, 0.5 mL of a toluene solution of 10% tri-tert-butylphosphine was added, and 60 mL of toluene was added. The resulting solution was heated to 90°C and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and dichloromethane and dried over anhydrous sodium sulfate. After distilling off the organic liquid phase, the product was purified by column chromatography with dichloromethane and methanol. After drying, 900 mg of orange powder was obtained with a yield of 91.8%.

[0042] Product Characterization: 1 H NMR (600MHz, Chloroform-d) δ10.00(s, 2H), 9.42(d, J=5.3Hz, 2H), 8.26(dd, J=5.4, 2.3Hz, 2H), 8.21(s, 2H) ,7.98(d,J=7.9Hz,2H),7.6...

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Abstract

The invention provides a terpyridine derivative, which has characteristics of high fluorescence quantum yield and thermally activating delayed fluorescence, such that the terpyridine derivative can beused as the material for organic electroluminescent devices, especially for non-doped fluorescent agents, wherein the organic electroluminescent device formed by using the terpyridine derivative as the non-doped fluorescent agent has characteristics of low driving voltage, low efficiency roll-off, high efficiency and the like. The terpyridine derivative of the present invention can be used as thecomponent for forming the organic electroluminescent device with characteristics of low voltage driving, high efficiency and low efficiency roll-off.

Description

technical field [0001] The invention relates to a terpyridine derivative, a preparation method and an application, and belongs to the technical field of organic chemistry. Background technique [0002] An organic electroluminescent device is a light-emitting layer (EML) containing a light-emitting material sandwiched between an electron transport layer (ETL) and a hole transport layer (HTL), and a cathode (Al) and an anode (ITO) are further installed outside it. , Inject electrons and holes into the device by applying an external voltage and recombine in the light-emitting layer to form a device in which excitons emit photons and deactivate through the process of fluorescence or phosphorescence. Due to its full solid state, self-illumination, wide viewing angle, fast response, low driving voltage, low energy consumption and many other characteristics, it has great application prospects in the fields of display and white light lighting. [0003] In recent years, thermally ac...

Claims

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Application Information

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IPC IPC(8): C07D413/14C09K11/06H01L51/54
Inventor 张晓宏史益忠郑才俊
Owner SUZHOU UNIV
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