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Organic electronic material containing phenanthrozole compound as well as preparation method and application of organic electronic material

An organic electronic material and phenanthroazole technology, applied in the field of organic electronic materials containing phenanthroazole compounds and their preparation, and can solve problems such as undisclosed or guidance

Pending Publication Date: 2021-09-10
SHANGHAI CHUANQIN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Patent WO2017073842 discloses a series of phenanthrene azole compounds with the following general formula: The specific disclosed structural formulas are This patent obviously pays attention to the unique properties of phenanthrene azoles, but does not disclose or guide the introduction of groups at the 9 and 10 positions of phenanthrene to prepare new compounds and the effects of applications

Method used

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  • Organic electronic material containing phenanthrozole compound as well as preparation method and application of organic electronic material
  • Organic electronic material containing phenanthrozole compound as well as preparation method and application of organic electronic material
  • Organic electronic material containing phenanthrozole compound as well as preparation method and application of organic electronic material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] The synthesis of embodiment 1 compound 3

[0075]

[0076] Synthesis of intermediate 1: o-bromophenylacetic acid (10g, 46.50mmol), 2-phenylbenzoxazole-4-boronic acid (10.7g, 48.85mmol) and potassium carbonate (9.6g, 69.46mmol) were added to the three ports In the flask, add toluene (60mL), ethanol (30mL) and deionized water (30mL), after passing nitrogen for 10min, add Pd(PPh 3 ) 2 Cl 2 (0.1g), reflux for 24 hours, cool, add 100mL of toluene, adjust the pH of the aqueous phase to 21 h 16 NO 3 ,330.1125,found,330.1122.

[0077] Synthesis of Compound 3: Add Intermediate 1 (10.0g, 30.36mmol) and DCM (20mL) to a three-necked flask and stir, then add CF 3 SO 3 H (10g, 66.64mmol) and Tf 2 O (10g, 35.44mmol) was dissolved after stirring, and stirred for 20h. TLC showed that the reaction was about 80%, and the reaction was stopped. While stirring, the reaction solution was slowly poured into 30mL of water, filtered, and washed until neutral. After the filter cake was...

Embodiment 2

[0078] The synthesis of embodiment 2 compound 4

[0079]

[0080] Compound 3 (5.0g, 16.06mmol), Tf 2 O (3.6g, 23.99mmol) and DCM (30mL) were added to a one-necked flask (can not be dissolved), and triethylamine (3.3g, 32.61mmol) was added dropwise to the one-necked flask, and the reaction was continued for 4h after the addition was completed. Add water (15 mL) dropwise, stir well, filter the solid, wash with ethanol, and dry to obtain 4.5 g. The mother liquor was separated, the organic phase was concentrated until viscous, filtered, washed with ethanol, and dried to obtain 1.6g, a total of 6.1g, with a yield of 85.7%. HRMS(ESI,m / z):[M+H]+calcd for:C 22 h 13 f 3 NO 4 S,444.0512,found,444.0511.

Embodiment 3

[0081] The synthesis of embodiment 3 compound 7

[0082]

[0083]Synthesis of Intermediate 2: Add o-bromophenylacetic acid (10g, 46.50mmol), 2-phenylbenzothiazole-4-boronic acid (12.5g, 49.00mmol) and potassium carbonate (9.6g, 69.46mmol) into a three-necked flask , add toluene (60mL), ethanol (30mL) and deionized water (30mL), after 10min of nitrogen gas, add Pd(PPh 3 ) 2 Cl 2 (0.1g), reflux for 24 hours, cool, add 100mL of toluene, and use 2N dilute hydrochloric acid solution to adjust the pH of the aqueous phase21 h 16 NO 2 S,346.0896,found,346.0898.

[0084] Synthesis of Compound 7: Intermediate 2 (10.0g, 28.95mmol) and DCM (20mL) were added to a three-necked flask and stirred (indissolvable), then CF was added 3 SO 3 H (10g, 66.64mmol) and Tf 2 O (10g, 35.44mmol) dissolved after stirring, and stirred for 20h. TLC showed that the reaction was about 80%, and the reaction was stopped. While stirring, the reaction solution was slowly poured into 30mL of water, filte...

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Abstract

The invention relates to an organic electronic material containing a phenanthrozole compound as well as a preparation method and application of the organic electronic material. The structure is shown as a structural formula (I), wherein Z1 is one of -N=, -NR10, -O- and -S-; Z2 is one of -N=, -NR11, -O- and -S-; at least one of Z1 and Z2 is -N=; R1, R10 and R11 are independently selected from C1-C12 alkyl, C6-C30 substituted or unsubstituted aryl, C3-C30 substituted or unsubstituted heteroaryl, and C3-C30 substituted or unsubstituted heteroaryl; and R3 is one of hydrogen, deuterium, halogen, a hydroxyl group, a trifluoromethanesulfonate group, a C1-C12 alkyl group, a C6-C30 substituted or unsubstituted aryl group, and a C3-C30 substituted or unsubstituted heteroaryl group.

Description

Technical field: [0001] The present invention relates to the technical field of organic electroluminescence, and more specifically, relates to an organic electronic material containing phenanthrozole compounds and its preparation method and application. Background technique: [0002] Organic electroluminescent devices (OLEDs) are a new type of display technology. Each pixel can be switched freely and emits light actively, which makes the display response time short and the color contrast high; the driving voltage can reduce energy consumption; the use of organic materials makes the device more Thin and light, environmentally friendly; and the diversified choices of substrates provide the possibility of flexible and transparent displays, which are widely used in mobile phones, flat panel displays, TVs, lighting and automotive displays. [0003] Originally invented by Dr. Deng Qingyun and Steven VanSlyke of Eastman Kodak, OLED adopts a sandwich structure, that is, the organic ...

Claims

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Application Information

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IPC IPC(8): C07D263/52C07D277/60C07F5/02C07D413/04C07D413/14C07D495/04C07D413/10C07D417/04C07D417/14C07D417/10C09K11/06H01L51/50H01L51/54
CPCC07D263/52C07D277/60C09K11/06C07F5/025C07D413/04C07D413/14C07D495/04C07D413/10C07D417/04C07D417/14C07D417/10C09K2211/1033C09K2211/1007C09K2211/1011C09K2211/1096C09K2211/1037C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H10K85/615H10K85/631H10K85/626H10K85/633H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576H10K85/342H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171H10K50/18
Inventor 苏艳周海涛章宇赵振宏郭世艳黄珠菊
Owner SHANGHAI CHUANQIN NEW MATERIAL CO LTD
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