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Heat-resistant organic electronegative semiconductor

A technology of organic semiconductors and compounds, applied in the field of heat-resistant organic electronegative semiconductors, which can solve the problems of short lifespan of heat resistance

Active Publication Date: 2015-02-04
冠能光电材料(深圳)有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, Kido et al. reported some electron transport materials composed of benzene ring and pyridine (Adv.Func.Mater., 2011, 21, pp36), but the electron mobility is still less than 2*10 -4 cm 2 / Vs, and the heat resistance of the material is at 60 o C short life under working conditions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Example 1: Synthesis of electron transport material 38

[0087]

[0088] Synthesis of compound TM-1: Add 20.50g of phenanthrenequinone, 48g of bromine, 1.0g of benzoyl peroxide and 300ml of nitrobenzene to reflux for 2-3 hours, cool to room temperature, filter, wash the solid with 400ml of ethanol and dry to obtain 29.21g of TM- 1, the yield is 82%;

[0089] Synthesis of compound TM-2: Heat 29.21g TM-1, 18.44g dibenzyl ketone, 5.00g potassium hydroxide and 350ml methanol, heat up to 50°C, react for 5-6 hours, cool down to room temperature, filter, wash the solid with water first, then wash with methanol Washing, drying obtains 32.5g TM-2, and yield is 76%;

[0090] Synthesis of compound TM-3:With 32.5g of TM-2, 9.2g of trimethylsilylacetylene and 250ml of xylene, the reaction was refluxed overnight, then lowered to room temperature, filtered, and the solid was purified by column to obtain 16.86g of TM-3 with a yield of 46% ;

[0091] Synthesis of compound...

Embodiment 2

[0093] Example 2: Synthesis of electron transport material 45

[0094]

[0095] Synthesis of Compound 45: 1.00g TM-4, 2.22g Pienalate , 0.10g palladium acetate, 0.20g S-Phos, 1.32g of potassium carbonate, 15ml of ethylene glycol dimethyl ether and 10ml of water, nitrogen replacement, then warming up to reflux, then cooling to room temperature, splitting, and passing the crude product through the column to obtain 1. 0g of product compound 45, yield: 60%, product characterization: Tg=200 degrees, PL=417nm, MS=370 degrees.

Embodiment 3

[0096] Example 3: Synthesis of electron transport material 51

[0097]

[0098] Synthesis of compound 51: 1.00g TM-4, 2.00 Pienalate , 0.10g palladium acetate, 0.20g S-Phos, 1.32g of potassium carbonate, 15ml of ethylene glycol dimethyl ether and 10ml of water, nitrogen replacement, then warming up to reflux, then cooling to room temperature, splitting, and passing the crude product through the column to obtain 0.9g of product 51, yield: 64%, product characterization: Tg=193 degrees, PL=418nm, MS=400 degrees.

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Abstract

The invention discloses a heat-resistant organic electronegative semiconductor. Electrophilic groups EW1 and EW2 are connected with aromatic heterocycle-substituted benzophenanthrene compound structural bond to obtain compounds (I). The heat-resistant organic electronegative semiconductor can be used in organic photoelectric electronic devices to enhance the efficiency of the devices, lower the working voltage of the devices and prolong the high-temperature service life.

Description

technical field [0001] The present invention relates to an organic light-emitting material and its application in an organic light-emitting device, especially a heat-resistant high-electron organic semiconductor, which can be applied to an organic electronic device, such as an organic light-emitting device OLED, an organic photovoltaic OPV, an organic thin-film transistor OTFT, Improve device performance. Background technique [0002] Organic semiconductor materials are new types of optoelectronic materials. Its large-scale research originated in 1977 by Shirakawa Hideki, A. Heeger and A. McDiamid who jointly discovered doped polyacetylene with a conductive car up to copper level. Subsequently, in 1987, C. Tang of KodaK Company invented the organic small molecule light-emitting diode (OLED), and in 1990, R. Friend and A. Holmes of Cambridge University invented the polymer light-emitting diode P-OLED, and in 1998, S. Forrest and M. Thomson invented a more efficient organic p...

Claims

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Application Information

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IPC IPC(8): C07D213/06C07D401/14C07D213/22C07F7/10C07D239/26C07D241/12C07D235/18C07C15/38C07C255/52C07D251/24C07D285/14H01L51/54
CPCC07C15/38C07C255/52C07D213/06C07D213/22C07D213/57C07D235/18C07D239/26C07D241/12C07D251/24C07D285/14C07D401/14C07F7/0812C07C2603/42H10K85/656H10K85/622H10K85/626H10K85/654H10K85/6572
Inventor 李晓常曾纪森
Owner 冠能光电材料(深圳)有限责任公司
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