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Organic aromatic amine luminescent material containing seven-membered ring

A technology of aromatic amines and luminescent materials, applied in luminescent materials, organic chemistry, electrical components, etc., to achieve good hole injection and hole transport capabilities, improved power efficiency and external quantum efficiency, and reduced driving voltage

Inactive Publication Date: 2019-02-22
烟台九目化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented design allows for better control over how much energy enters into organic molecules by providing certain atoms or groups on their surface called donors (electron receptive). These donators help transfer these charged particles from one part of the molecule to another part during operation. Additionally, this new chemical entity helps create stronger bonds between different parts of the substance due to its ability to absorb holes effectively without losing stability. Overall, this technology improves both performance and lifespan of devices made up of them.

Problems solved by technology

Technological problem addressed in this patents relates to improving the performance and lifespan of optoeletronic diodes (ODNs) while reducing costs associated with production processes or increasing productivity. Specifically, it highlights the challenges faced when developing new materials due to factors like low cost, lack of durability over multiple cycles, limited usable lifetime caused by reduced luminosity factor, narrow spectral bandwidth required for efficient operation, and strong yellowish green background colors.

Method used

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  • Organic aromatic amine luminescent material containing seven-membered ring
  • Organic aromatic amine luminescent material containing seven-membered ring
  • Organic aromatic amine luminescent material containing seven-membered ring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the synthesis of compound 2

[0031]

[0032] In a 500ml three-necked bottle, add 3.28g of magnesium flakes (134mmol) under the condition of nitrogen gas, at room temperature, prepare raw material A40g (141mol), THF 160g solution, add a small amount of preparation solution to the three-necked bottle, so that the liquid level is just over the magnesium After adding the ingredients, stir and heat up. When the temperature rises to 64°C, the reaction is initiated. When the temperature is lowered to 55°C-65°C, the raw material A / THF solution is added dropwise. Cool down to room temperature, hydrolyze, extract with toluene, wash with water, pass through a silica gel column, remove the solvent, and recrystallize with toluene to obtain 35g of white intermediate A with a yield of 76.5% and a purity of 99.1%. The molar ratio of tribenzocycloheptenone to raw material A is 1.1:1, and the molar ratio of raw material A to magnesium sheet is 1:0.95.

[0033] In a 500...

Embodiment 2

[0035] Embodiment 2: the synthesis of compound 14

[0036]

[0037] Under nitrogen protection, weigh 30g raw material C (177mmol), 37.8g raw material D (177mmol), 42.6g sodium tert-butoxide (443mmol), 0.40g Pd(OAc)2 (1.77mmol), 1.55g C10104R3 (3.54 mmol), stirred and mixed with toluene, heated to 70-75°C, refluxed for 2-3 hours, sampled and spotted on the plate, it showed that there was no raw material C remaining; naturally cooled to room temperature, washed with water, passed through a silica gel column, refined with toluene, and dried to obtain 43g of intermediate B, yield: 80.4%, HPLC: 99.6%. The molar ratio of raw material C, raw material D, and sodium tert-butoxide is 1:1:2.5.

[0038] In a 500ml three-necked flask, under nitrogen gas, add 30g of compound intermediate A (90mmol), 27.1g of intermediate B, add 300g of dichloroethane, and add boron trifluoride ether solution (BF3 Et2O90g, 3 times that of intermediate A), after dropping, keep temperature at 0-10°C, keep...

Embodiment 3

[0040] Embodiment 3: the synthesis of compound 47

[0041]

[0042] Under nitrogen protection, weigh 30g raw material C (177mmol), 70.5g raw material E (177mmol), 42.6g sodium tert-butoxide (443mmol), 0.40g Pd(OAc)2 (1.77mmol), 1.55g C10104R3 (3.54 mmol), stirred and mixed with toluene, heated to 70-75°C, refluxed for 3-5 hours, sampling TLC showed that no raw material C remained; naturally cooled to room temperature, washed with water, passed through a silica gel column, refined with toluene, and dried to obtain 55g Intermediate C, yield: 63.9%, HPLC: 99.8%. The molar ratio of raw material C, raw material E, and sodium tert-butoxide is 1:1:2.5.

[0043]In a 500ml three-neck flask, under nitrogen gas, add 30g of compound intermediate A (90mmol), 43.6g of intermediate C (90mmol), add 300g of dichloroethane, and add boron trifluoride ether dropwise at a temperature of 0-10°C Solution (BF 3 ·Et 2 (2) 150g, 5 times that of intermediate A), after dripping, temperature contro...

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Abstract

The invention relates to an organic aromatic amine luminescent material containing a seven-membered ring, and belongs to the technical field of organic photoelectric materials. An organic compound with organic aromatic amine having the seven-membered ring as a core structure is used for an OLED device as a light-emitting layer or an electron transfer layer material. The material has good molecularstability, and the prepared OLED device has superior photoelectric performance, high thermal stability, low driving voltage and high efficiency. The service life of the device can be prolonged, and the requirements of device manufacturers can be met.

Description

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Claims

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Application Information

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Owner 烟台九目化学股份有限公司
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