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Nitrogen-containing seven-membered heterocyclic derivative compound, preparation method thereof and application of compound to organic light-emitting device

A compound and seven-membered ring technology, applied in the field of compounds containing nitrogen-containing seven-membered ring derivatives, can solve different problems, improve current efficiency and lifespan, improve high fluorescence radiation efficiency, and improve hole injection and transport performance Effect

Inactive Publication Date: 2019-04-05
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Nitrogen-containing seven-membered heterocyclic derivative compound, preparation method thereof and application of compound to organic light-emitting device
  • Nitrogen-containing seven-membered heterocyclic derivative compound, preparation method thereof and application of compound to organic light-emitting device
  • Nitrogen-containing seven-membered heterocyclic derivative compound, preparation method thereof and application of compound to organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Embodiment 1: the synthesis of intermediate Cn:

[0081]

[0082] (1) In a 250mL three-necked flask, add 0.1mol raw material I, 0.15mol raw material J, 0.3mol sodium tert-butoxide, 1×10 -3 mol Pd 2 (dba) 3 , 1×10 -3 mol tri-tert-butylphosphine, 150mL toluene, heated to 95°C, refluxed for 24 hours, sampled and plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the intermediate Sn.

[0083] (2) In a 250mL three-neck flask, add 150mL of liquid ammonia, 0.05mol of intermediate Sn, and 0.15mol of potassium tert-butoxide under an atmosphere of nitrogen gas, place the reaction solution under a 500w xenon lamp for photochemical reaction for 1 hour, and then add nitric acid The reaction was quenched with ammonium, the residue was added to water after the liquid ammonia evaporated, the aqueous phase was extracted with dichloromethane, dried over anhydrous magnesium sulfate, the ...

Embodiment 2

[0084] Embodiment 2: the synthesis of intermediate Dn:

[0085]

[0086] (1) Weigh the raw material K and phenylboronic acid, dissolve them in a mixed solvent of toluene and ethanol with a volume ratio of (2~3):1, and add potassium carbonate aqueous solution and tetrakistriphenylphosphorous palladium under an inert atmosphere, at 95~110 Reaction at ℃ for 10-24 hours, cooled to room temperature, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the intermediate Tn; wherein the molar ratio of the raw material K to phenylboronic acid was 1: (1.2-1.5); the bromide raw material K and carbonic acid The molar ratio of potassium is 1:(2.0~3.0); the molar ratio of raw material K and tetrakistriphenylphosphorous palladium is 1:(0.01~0.02);

[0087] (2) Dissolve stannous chloride in 50mL of concentrated hydrochloric acid, slowly drop the concentrated hydrochloric acid solution of stannous chloride into the intermediate Tn, stir at room temp...

Embodiment 3

[0090] Embodiment 3: the synthesis of intermediate En:

[0091]

[0092]

[0093] (1) Weigh raw material M1 and raw material N1, add potassium phosphate aqueous solution, copper nanoparticles and toluene, react at 110°C for 2 hours, cool to room temperature, extract with ethyl acetate, wash with water, dry, pass through a silica gel column, Obtain intermediate Y1; wherein the molar ratio of raw material M1 to raw material N1 is 1:(1.0~1.4); the molar ratio of raw material M1 to potassium phosphate is 1:(2.0~3.0);

[0094] (2) In a 250mL three-necked flask, add methylmagnesium iodide and intermediate Y1 into tetrahydrofuran at 0°C under a nitrogen atmosphere, stir at room temperature for 2 hours, cool the reaction mixture to 0°C, add saturated ammonium chloride to quench The reaction was extinguished, stirred for 30 min, and evaporated in vacuum. The residue was extracted with chloroform, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated in...

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Abstract

The invention discloses a nitrogen-containing seven-membered heterocyclic derivative compound, a preparation method thereof and an application of the compound to an organic light-emitting device, andbelongs to the technical field of semiconductors. The structure of the organic compound is as shown in a general formula as shown in the specification. The compound has higher glass transition temperature, molecular heat stability and Eg and suitable HOMO and LUMO energy level, a device structure is optimized, photoelectric property of the OLED (organic light emitting diode) can be effectively improved, and the service life of the OLED can be effectively prolonged.

Description

technical field [0001] The invention relates to a nitrogen-containing hetero seven-membered ring derivative compound, a preparation method and its application in an organic electroluminescent device, belonging to the technical field of semiconductors. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at bot...

Claims

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Application Information

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IPC IPC(8): C07D223/14C07D491/048C07D487/04C07D491/153C07D495/14C07D487/14C07D491/056C07D497/04C07D491/052C07D498/04C07D495/04C07D498/14C07D491/044C07D519/00C09K11/06H01L51/50H01L51/54
CPCF21K9/00C09K11/06C07D223/14C07D487/04C07D487/14C07D491/044C07D491/048C07D491/052C07D491/056C07D491/153C07D495/04C07D495/14C07D497/04C07D498/04C07D498/14C07D519/00C09K2211/1092C09K2211/1088C09K2211/1033C09K2211/1011C09K2211/1007C09K2211/1029H10K85/615H10K85/657H10K85/6572H10K50/18H10K50/15H10K50/11
Inventor 庞羽佳唐丹丹张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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