A thermally active delayed fluorescence organic compound with 2-cyanopyrazine as acceptor and its preparation and application

A technology of organic compounds and delayed fluorescence, which is applied in the fields of organic chemistry, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., and can solve problems such as spectrum being affected by solvent polarity, large excited state dipole moment, and device stability degradation , to achieve good industrial application prospects, good photoelectric performance, and reduce the effect of impact

Active Publication Date: 2021-01-15
ZHEJIANG HONGWU TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although TADF materials have the above-mentioned advantages, because TADF molecules are generally charge-transfer molecules, charge separation in the excited state often leads to a large excited-state dipole moment, so the spectrum in the solution is affected by the polarity of the solvent. , the spectrum in the device is affected by the polarity of the surrounding molecules
TADF molecules are generally used as guest molecules in the device and doped with strongly polar host molecules to form the light-emitting layer, which will cause the spectrum in the device to red-shift, and the red-shift and broadening of the spectrum will further lead to a decrease in the stability of the device. question

Method used

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  • A thermally active delayed fluorescence organic compound with 2-cyanopyrazine as acceptor and its preparation and application
  • A thermally active delayed fluorescence organic compound with 2-cyanopyrazine as acceptor and its preparation and application
  • A thermally active delayed fluorescence organic compound with 2-cyanopyrazine as acceptor and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: the synthesis of compound 19TCzPZCN:

[0043] synthetic route:

[0044]

[0045] (1) Add 2.79g (10.0mmol) 3,6-di-tert-butylcarbazole and 6.52g (20.0mmol) cesium carbonate into a 100mL three-necked flask, fill with nitrogen for 3 times to remove oxygen, and inject 1.31mL under nitrogen atmosphere (12mmol) o-fluorobromobenzene, 15mL DMF ultra-dry solvent, heated to reflux at 160 degrees Celsius for 24h. After the reaction was monitored by TCL, the reaction system was cooled to room temperature, extracted with 150 mL of ethyl acetate and 300 mL of saturated brine, then washed with saturated brine (100 mL×3) for 3 times, dried over anhydrous sodium sulfate for 10 min, filtered, concentrate. The crude product was passed through a silica gel column (5×10 cm), and the pure product was isolated and dried in vacuo to obtain 4.01 g of product 19-1 with a yield of 92%.

[0046] 1 H NMR (400MHz, CDCl3): δ=8.14(s, 2H), 7.84(d, J=8Hz, 1H), 7.51-7.31(m, 5H), 6.99(...

Embodiment 2

[0051] Embodiment 2: the synthesis of compound 24 2TCzPZCN:

[0052]

[0053] (1) Add 2.79g (10.0mmol) 3,6-di-tert-butylcarbazole, 6.52g (20.0mmol) cesium carbonate into a 100mL three-necked flask, fill with nitrogen for 3 times to remove oxygen, and inject 0.78g under nitrogen atmosphere (4mmol) 2,5-difluorobromobenzene, 15mL DMF ultra-dry solvent, heated to reflux at 160°C for 24h. After the reaction was monitored by TCL, the reaction system was cooled to room temperature, extracted with 150 mL of ethyl acetate and 300 mL of saturated brine, then washed with saturated brine (100 mL×3) for 3 times, dried over anhydrous sodium sulfate for 10 min, filtered, concentrate. The crude product was passed through a silica gel column (5×10 cm), the pure product was isolated, and vacuum-dried to obtain 2.59 g of product 24-1 with a yield of 91%.

[0054] 1 H NMR (400MHz, CDCl 3 ): δ=8.18-8.17(m, 4H), 8.11(d, J=4Hz, 1H), 7.75-7.72(m, 1H), 7.63(d, J=12Hz, 1H), 7.54(m, 4H) ,7.52(d,...

Embodiment 3

[0063] light emitting devices such as figure 1 As shown, it specifically includes: transparent substrate layer 1 / ITO anode layer 2 / hole injection layer 3 (MoO 3 , thickness 3nm) / hole transport layer 4 (mCP, thickness 40nm) / light-emitting layer 5 (mCP or DPEPO and compound 19 are mixed according to the weight ratio of 10~30:90~70, thickness 30nm) / electron transport layer 6 ( PPT, thickness 40nm) / electron injection layer 7 (Liq, thickness 2nm) / cathode reflective electrode layer 8 (Al, thickness 10nm). The structural formulas of the materials involved are as follows:

[0064]

[0065] Concrete preparation process is as follows:

[0066] The transparent substrate layer 1 is a transparent substrate, such as transparent PI film, glass and the like. The ITO anode layer 2 (with a film thickness of 150nm) was washed, that is, alkali washing, pure water washing, drying, and ultraviolet-ozone washing were performed in order to remove organic residues on the transparent ITO surface....

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Abstract

The invention discloses a thermally active delayed fluorescence organic compound with 2-cyanopyrazine as an acceptor and its preparation and application. The structure of the thermally active delayed fluorescent organic compound is shown in the general formula (1). The compound is based on the light emitting mechanism of TADF and is used as a light emitting layer material in an organic electroluminescent device. The device produced by the invention has good photoelectric performance and can meet the requirements of panel manufacturers.

Description

technical field [0001] The invention relates to the field of semiconductor technology, in particular to a thermally active delayed fluorescence compound with a small excited state dipole moment using 2-cyanopyrazine as an acceptor and its use as a light-emitting layer guest material in an organic electroluminescent device on the application. Background technique [0002] The application of organic light-emitting diodes (OLEDs) in large-area flat-panel displays and lighting has attracted extensive attention from both industry and academia. However, traditional organic fluorescent materials can only use 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). The external quantum efficiency is generally lower than 5%, and there is still a big gap with the efficiency of phosphorescent devices. Although phosphorescent materials enhance intersystem crossing due to the strong spin-orbit coupl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/10C07D403/14C07D519/00C07D241/24C07D401/14C07D401/10C07D413/10C07D413/14C07D417/10C07D417/14C09K11/06H01L51/54
CPCC07D403/10C07D403/14C07D519/00C07D241/24C07D401/10C07D401/14C07D413/10C07D413/14C07D417/10C07D417/14C09K11/06C09K2211/1044C09K2211/1033C09K2211/1037H10K85/656H10K85/654H10K85/657H10K85/6572
Inventor 艾琦刘俊源段科张其胜
Owner ZHEJIANG HONGWU TECH CO LTD
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