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Organic compound and application thereof

A technology of organic compounds and chemical bonds, applied in the field of organic electroluminescent materials, to achieve the effects of improving luminous efficiency and stability, best luminous effect, and excellent hole transport performance

Pending Publication Date: 2022-07-22
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the hole transport materials for commercial mass production are mainly aromatic amine materials. Due to the different materials used in devices, the currently used materials and device structures cannot completely solve the problems of OLED product efficiency, lifespan, cost, etc.

Method used

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  • Organic compound and application thereof
  • Organic compound and application thereof
  • Organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0153] Synthesis Example 1: Organic Compound C1

[0154]

[0155] (1) Synthesis of intermediate C1-1

[0156] In a 1000mL single-necked flask equipped with magnetic stirring at room temperature, add 2,3-dichloronitrobenzene (30g, 156.25mmol), phenylboronic acid (47.63g, 390.64mmol), tris(dibenzylacetone)dipalladium ( 0)Pd 2 (dba) 3 (2.86g, 3.13mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl s-Phos (2.57g, 6.25mmol), potassium phosphate (66.33g, 312.51mmol), dioxygen 500 mL of hexacyclic ring, 50 mL of water, turn on stirring, replace nitrogen for 3 times, heat up to 100°C, and react overnight. As monitored by thin layer chromatography (TLC), the reaction of the starting material was complete. The reaction solution was cooled to room temperature, extracted with ethyl acetate, the supernatant liquid was taken, spin-dried, petroleum ether (PE):dichloromethane (DCM)=10:1 was passed through a 100-200 mesh silica gel column to obtain 40.56g of an oily liquid .

[015...

Synthetic example 2

[0162] Synthesis Example 2: Organic Compound C2

[0163]

[0164] (1) Synthesis of intermediate C2-2

[0165] Intermediate C1-2 (15 g, 61.14 mmol), 2-bromo-9,9-dimethylfluorene (16.70 g, 61.14 mmol), Pd 2 (dba) 3 (0.56g, 0.61mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr.HCl (0.52g, 1.22mmol), NaOBu-t (11.75g, 122.29mmol) It was added to 500 mL of toluene, stirred evenly, and heated to 110° C. under nitrogen protection for overnight reaction. TLC monitoring showed that the reaction of the starting materials was complete. After cooling down, use a silica gel column to remove the solvent and remove 100 mL of methanol to precipitate a solid. The solid was collected, separated by column, PE:DCM=20:1, washed with methanol to obtain 12.85g of intermediate C2-2.

[0166] (2) Synthesis of organic compound C2

[0167] Intermediate C2-2 (12.85 g, 29.37 mmol), 2-bromo-9,9-diphenylfluorene (14 g, 35.24 mmol), Pd 2 (dba) 3 (0.54g, 0.59mmol), (t-Bu) 3 P (0.24 g, 1...

Synthetic example 3-14

[0170] The process route of Synthesis Example 3-14 is the same as that of Synthesis Example 1-2, the difference is that the raw materials used are different. The raw materials, target products and result characterization data are shown in Table 1; in Table 1, raw material A represents Raw material B indicates Raw material C means

[0171] Table 1

[0172]

[0173]

[0174]

[0175]

[0176] Quantum chemical calculations for compounds:

[0177] Among all the electron-filled orbitals of a compound, the orbital with the highest energy for the electron is called the highest occupied molecular orbital (HOMO). Conversely, among all the unfilled electron orbitals, the orbital with the lowest electron energy is called the lowest unoccupied molecular orbital (LUMO). The transport of charges in the material is the process by which electrons are continuously escaping from the HOMO and adding electrons to the LUMO. In quantum chemistry, the degree of overlap between HO...

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Abstract

The invention provides an organic compound and application thereof, the organic compound has a structure as shown in a formula I. Through the design of a molecular structure, the stacking density of molecules is improved, so that the organic compound has excellent hole transport performance, the HOMO energy level of the compound is regulated and improved, and the organic compound is better matched with an anode material; the hole injection and transmission capability of the compound is improved, the acquisition of low voltage is facilitated, and the carrier transmission stability of the compound in an electric field environment is obviously improved. Due to the special tetrahedral structure of the organic compound, the organic compound can be used for preparing a good amorphous film, so that the organic compound has good film-forming property when being used as an organic electroluminescent device material. The organic compound is applied to the organic electroluminescent device, is especially suitable for being used as a hole transport layer material and / or an electron barrier layer material, and can effectively improve the luminous efficiency and stability of the device, prolong the service life of the device, reduce the voltage and achieve a better luminous effect.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound and its application. Background technique [0002] In recent years, optoelectronic devices based on organic materials have become more and more popular. Compared with inorganic materials, the inherent flexibility of organic materials makes them suitable for fabrication on flexible substrates, and a variety of optoelectronic products can be designed and produced according to demand. Currently known organic optoelectronic devices include organic light emitting diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLEDs have the advantages of self-luminescence, high contrast, wide color gamut, flexibility, and low power consumption. Especially rapidly, it has achieved commercial success and is widely used in flexible displays, flat panel displays, and solid-state li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07D213/73C07D239/42C07D471/04C07D237/20C07D217/22C07D239/84C07D215/38H01L51/50H01L51/54
CPCC07C211/61C07D213/73C07D239/42C07D471/04C07D237/20C07D217/22C07D239/84C07D215/38C07C2603/18C07C2603/26C07C2603/94C07C2603/24C07C2603/42H10K85/615H10K85/622H10K85/624H10K85/626H10K85/636H10K85/633H10K85/654H10K85/6572H10K50/15H10K50/17H10K50/18C07D213/74C07D241/20C07C2602/10
Inventor 高文正曾礼昌孙恩涛王志鹏刘叔尧李之洋马腾陈继荣
Owner BEIJING ETERNAL MATERIAL TECH
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