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Compound taking anthrone derivative as core and application of compound in OLED device

An anthrone derivative and compound technology, applied in the application field of organic electroluminescent devices, can solve problems such as differences, and achieve the effects of avoiding aggregation, improving device life, and facilitating energy transfer.

Pending Publication Date: 2020-04-07
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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  • Compound taking anthrone derivative as core and application of compound in OLED device
  • Compound taking anthrone derivative as core and application of compound in OLED device
  • Compound taking anthrone derivative as core and application of compound in OLED device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The synthesis of embodiment 1 intermediate A

[0053]

[0054] Under nitrogen atmosphere, weigh raw material I, raw material II, KOAc and Pd(dppf)Cl 2 Dissolve in 1,4-dioxane, and react at 130°C for 5 hours. After completion of the reaction, water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate to obtain a crude product, which was separated and purified by silica gel column chromatography to obtain the target product.

[0055] The molar ratio of the raw material I to the raw material II is 0.8~2:1; Pd(dppf)Cl 2 The molar ratio of KOAc to raw material I is 0.0018-0.004:1, and the molar ratio of KOAc to raw material I is 2.0-5.0:1.

[0056] Take the synthesis of intermediate A1 as an example:

[0057]

[0058] In a 250mL three-necked flask, nitrogen gas was introduced, and 10.0mol of raw material Ⅰ-1, 12.0mol of raw material Ⅱ-1, 0.3g of Pd(dp...

Embodiment 2

[0063] The synthesis of embodiment 2 intermediate B

[0064]

[0065] Under a nitrogen atmosphere, weigh raw material III and dissolve it in tetrahydrofuran, then add raw material IV and tetrakis(triphenylphosphine) palladium, stir the mixture, then add potassium carbonate aqueous solution, and mix the above reactants at a reaction temperature of 70-90 °C, heat to reflux for 5-20 hours. After the reaction, cooling and adding water, the mixture was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, the obtained residue was separated and purified by silica gel column chromatography to obtain intermediate B;

[0066] The molar ratio of raw material III to raw material IV is 1:1.0 to 1.5, the molar ratio of tetrakis(triphenylphosphine) palladium to raw material III is 0.001 to 0.02:1, and the molar ratio of potassium carbonate to raw material III is 1.0 to 2.0:1 , the ratio of tetrahydrofuran t...

Embodiment 3

[0074] The synthesis of embodiment 3 compound C13

[0075]

[0076] 11.11mmol (3'-chloro-[1,1'-biphenyl]-4-yl)(phenyl)methanone, 7.40mmol 1-(4,4,5,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)dibenzo[f,H]isoquinoline, 0.101g Pd(OAc) 2 , 7.21mmolCs 2 CO 3 Mix with 14.42mmol Xphos; under the protection of nitrogen, add the above mixture to the mixed solution of toluene / water / ethanol, the volume ratio of toluene / water / ethanol in the mixed solution is 3:1:1, under the condition of 110 ℃, microwave reaction 3 hours. After the reaction was finished, extract the organic layer with dichloromethane, and then use anhydrous MgSO 4 Drying, further separation and purification by TLC (thin layer chromatography) to obtain the target product, HPLC purity 99.8%, yield 66%;

[0077] Elemental analysis structure (molecular formula C 36 h 23 NO): Theoretical C, 89.05; H, 4.77; N, 2.88; O, 3.29; Tested: C, 89.03; H, 4.75; N, 2.86;

[0078] HPLC-MS: The molecular weight of the material is 485....

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Abstract

The invention discloses a compound taking an anthrone derivative as a core and an application of the compound in an OLED device. A parent nucleus and a branched chain of the compound are both electronic groups, so the compound has quite high electron transmission rate and can be used as an electron transport material, the electron transmission and injection performance is improved, the deep HOMO energy level can effectively prevent holes from being transmitted to one side of an electron transmission layer, the carrier concentration of the light-emitting layer is balanced, so that the light-emitting efficiency of the device is improved; when the compound is used as a light-emitting layer material to be applied to an organic light-emitting diode, good photoelectric properties can be obtained, and the requirements of panel manufacturing enterprises can be met.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with anthrone derivatives as the core and its application in organic electroluminescent devices. Background technique [0002] At present, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, compared with actual product application requirements, the luminous efficiency and service life of OLED devices Further improvement is required. Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. In order to realize the continuous improvement of the performance of OLED devices, not only the innovation of OLED device structure and manufacturing process is required, but also the continuous research ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C07D405/10C07D471/04C07D409/10C07D401/10C07F7/10C09K11/06H01L51/50H01L51/54
CPCC07D221/18C07D405/10C07D471/04C07D409/10C07D401/10C07F7/10C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092H10K85/6576H10K85/6574H10K85/40H10K85/6572H10K50/00
Inventor 李崇梁丽王芳谢丹丹
Owner JIANGSU SUNERA TECH CO LTD
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