Organic electronic material containing dibenzoheterocycle substituted phenanthrene and anthracene and application of organic electronic material

A technology of organic electronic materials and diphenyl, which is applied in the direction of luminescent materials, organic chemistry, organic chemical methods, etc., can solve the problems of undisclosed compounds and application effects, and no mention of dibenzothiophene and application effects, etc., to achieve Improve luminous efficiency, enhance charge transport performance, synthesize simple effects

Pending Publication Date: 2021-11-05
SHANGHAI CHUANQIN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The article (Jinhai Huang, Jian-Hua Su, He Tian. The development of anthracene derivatives for organic light-emitting diodes, J. Mater. Chem., 2012, 22, 10977) reviewed the application of anthracene in devices, and the patent JP2005041843 developed Anthracene is connected to a phenanthrene group at the 9 and 10 positions, and the specific structural formula is This patent fully considers the characteristics of anthracene and phenanthrene, but does not disclose or guide the situation and application effect of anthracene direct phenanthrene compounds at other positions
Patent CN110294735 also discloses a series of compounds with anthracene and phenanthrene as the core, but it does not mention the situation and application effect of connecting dibenzofuran or dibenzothiophene to phenanthrene

Method used

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  • Organic electronic material containing dibenzoheterocycle substituted phenanthrene and anthracene and application of organic electronic material
  • Organic electronic material containing dibenzoheterocycle substituted phenanthrene and anthracene and application of organic electronic material
  • Organic electronic material containing dibenzoheterocycle substituted phenanthrene and anthracene and application of organic electronic material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The synthesis of embodiment 1 compound 2

[0054]

[0055] Synthesis of Intermediate 2-1

[0056] In a three-necked flask, add 9-bromo-2-chlorophenanthrene (10g, 34.4mmol), 1-dibenzofuran boronic acid (7.6g, 36mmol), potassium carbonate (9.3g, 68mmol), then add 100mL toluene, 50mL Ethanol and 50mL deionized water, add 0.5gPd(PPh 3 ) 2 Cl 2 , heated to reflux for 5 hours under the protection of nitrogen, cooled, a solid precipitated out, filtered, the filter cake was rinsed with ethanol, dried, the filter cake was recrystallized with toluene, filtered, and dried to obtain 9.6 g of a solid with a yield of 75%.

[0057] Synthesis of compound 2

[0058] In a three-necked flask, add intermediate 2-1 (9g, 23.8mmol), 9-(phenyl-d5)-10-anthraceneboronic acid (7.9g, 26.2mmol), potassium carbonate (6.9g, 50mmol), and then add 100mL of toluene, 50mL of ethanol and 50mL of deionized water, add 0.5g of palladium acetate, 1g of Xphos (2-dicyclohexylphosphine-2',4',6'-triisopro...

Embodiment 2

[0059] The synthesis of embodiment 2 compound 26

[0060]

[0061] Synthesis of Intermediate 26-1

[0062] In a three-necked flask, add 2-chloro-9-iodo-10-phenylphenanthrene (15g, 36.2mmol), 1-dibenzofuran boronic acid (8.1g, 38mmol), potassium carbonate (10.3g, 68mmol), and Add 150mL toluene, 70mL ethanol and 70mL deionized water, add 0.5g Pd(PPh 3 ) 2 Cl 2 , heated to reflux for 5 hours under the protection of nitrogen, cooled, solids precipitated, filtered, the filter cake was rinsed with ethanol, dried, the filter cake was recrystallized with toluene, filtered, and dried to obtain 13.6 g of solids, with a yield of 83%.

[0063] Synthesis of compound 26

[0064] In a three-necked flask, add intermediate 26-1 (6g, 13.2mmol), 9-(phenyl-d5)-10-anthraceneboronic acid (4.4g, 14.5mmol), potassium carbonate (3.4g, 15mmol), and then add 80mL toluene, 40mL ethanol and 40mL deionized water, add 0.3g palladium acetate, 0.6g Xphos, heat to reflux for 5 hours under the protectio...

Embodiment 3

[0066] The synthesis of embodiment 3 compound 27

[0067]

[0068] In a three-necked flask, add intermediate 26-1 (6g, 13.2mmol), 9-(2-naphthyl)-10-anthraceneboronic acid (5.1g, 14.5mmol), potassium carbonate (3.4g, 15mmol), and then add 80mL toluene, 40mL ethanol and 40mL deionized water, add 0.3g palladium acetate, 0.6g Xphos, heat to reflux for 5 hours under the protection of nitrogen, cool, there is solid precipitation, filter, rinse the filter cake with ethanol, dry, and use the filter cake Toluene was recrystallized, filtered, and dried to obtain 5.8 g of solid, with a yield of 61%.

[0069] 1 H NMR (400MHz, CDCl 3 ,δ): 9.01-9.16 (m, 2H), 7.30-8.09 (m, 25H), 6.72-7.10 (m, 7H). HRMS(ESI,m / z):[M+H] + :723.2657.

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Abstract

The invention relates to an organic electronic material containing dibenzoheterocycle substituted phenanthrene and anthracene and an application of the organic electronic material. The structural formula of the organic electronic material is shown in the following structural formula I, wherein in the structural formula I, Ar1 is one of C12-C30 substituted or unsubstituted dibenzofuran and C12-C30 substituted or unsubstituted dibenzothiophene; R1 is one of hydrogen, deuterium, phenyl, tolyl, naphthyl and biphenyl; R2 to R17 are one of hydrogen, deuterium, C1-C12 substituted or unsubstituted alkyl, and C6-C30 substituted or unsubstituted aryl; and Ar2 is one of a C6-C30 substituted or unsubstituted aryl group and a C3-C30 substituted or unsubstituted heteroaryl group.

Description

Technical field: [0001] The invention belongs to the display technology field of organic electroluminescent devices, and more specifically relates to an organic electronic material containing dibenzoheterocyclic substituted phenanthrene and anthracene and its application. Background technique: [0002] Organic electroluminescent devices (OLEDs), as a new type of display technology, have the advantages of self-luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, and flexible fabrication. The unique advantages of flexible and transparent display panels and environmental friendliness can be applied to flat panel displays and new generation lighting, and can also be used as LCD backlight. [0003] An organic electroluminescent device is a device prepared by depositing a layer of organic materials between two metal electrodes by spin coating or vacuum evaporat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91C07D333/76C07B59/00C09K11/06H01L51/54
CPCC07D307/91C07D333/76C07B59/002C09K11/06C09K2211/1011C09K2211/1088C09K2211/1092C07B2200/05H10K85/626H10K85/615H10K85/6576H10K85/6574
Inventor 苏艳章宇周海涛罗鑫黄珠菊
Owner SHANGHAI CHUANQIN NEW MATERIAL CO LTD
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