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Compound containing azocine structure and application

The technology of a compound, azocine, is applied in the field of organic electroluminescent devices, which can solve problems affecting electronic transitions, device luminous effects, and lifetime effects, and achieve good application prospects, superior stability, and improved luminous efficiency and lifetime characteristics. Effect

Active Publication Date: 2021-12-03
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

Problems solved by technology

Therefore, the molecular structure of organic substances that make up the light-emitting layer will affect the transition of electrons, which will further affect the luminous effect and life of the device.

Method used

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  • Compound containing azocine structure and application
  • Compound containing azocine structure and application
  • Compound containing azocine structure and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of compound A1

[0023] The reaction equation is as follows:

[0024]

[0025] The synthetic method of parent M6 is as follows:

[0026] (1) Dissolve 100mmol of 7-methoxy-1-nitronaphthalene (a known compound, Cas:4900-68-9) in 200g of dichloroethane, pass nitrogen, control the temperature at 0-10°C, drop Add 97mmol of N-bromosuccinimide solution (17.3g of N-bromosuccinimide is dissolved in 70g of N,N-dimethylformamide), and the addition is completed dropwise in 30 minutes. After the dropwise addition, keep the temperature at 0-10°C for 4 hours, take a sample and detect it. After the reaction is completed, the product has a purity of 90%. Directly add sodium bisulfite aqueous solution for hydrolysis, the system produces a large amount of brick red solid, which is filtered directly. The filter cake was recrystallized once with dichloroethane to obtain compound M1 with a purity of 99.2% and a yield of 83.0%.

[0027] (2) Add 105mmol of co...

example 2

[0036] Example 2: Synthesis of Compound A10

[0037] The reaction equation is as follows:

[0038]

[0039] The synthesis method of the parent M6 refers to the experimental process of Example 1.

[0040]Put 30.7g (100mmol) of M6 and 32.2g (100mmol) of M7 (known compound, Cas:1034050-49-1) in 200g of xylene, then add 0.9g (10mmol) of N,N-dimethyl Ethylenediamine, 38.1g (200mmol) of cuprous iodide, 34.5g (250mmol) of potassium carbonate were passed through nitrogen, and the temperature was raised to 125-135°C for reaction, and the temperature was kept for 20 hours, and the reaction was completed. Cool down to about 50°C and wash with water. Then dry and pass through a 40 g silica gel column to remove the solvent. Then ethyl acetate and toluene were added for recrystallization to obtain 45 g of product, HPLC: 99.2%, yield: 81.9%.

[0041] The nuclear magnetic resonance instrument uses the Bruker model, 1 HNMR(CDCl3)1.78(s,6H),6.781-6.721(dd,1H),6.870-6.879(dd,1H),7.449-7....

preparation example

[0046] 1) Device glass substrate etching and cleaning. Prepare the glass substrate, first cover the glass substrate containing ITO on the surface with scotch tape, then cut it to expose the part to be etched, and then put it into the etching solution for etching (the etching solution depends on the volume A solution of hydrochloric acid and water in a ratio of 1:2). After etching for 15 hours, the glass substrate was successively put into an ultrasonic cleaner containing acetone and ethanol for cleaning for 1 hour. After cleaning, put it into a vacuum drying oven for drying treatment.

[0047] 2) Device anode bombardment treatment. Put the dried glass substrate into the pretreatment chamber of the OLED-V vacuum coating machine for plasma bombardment on the ITO surface of the device.

[0048] 3) Evaporation. After the pretreatment of the device glass plate is completed, the glass substrate is placed in the evaporation chamber of the multifunctional vacuum evaporation machin...

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Abstract

The invention relates to a compound containing an azocine structure, and belongs to the field of organic electroluminescent devices, the molecular structure general formula of the compound is as shown in the chemical Formula 1, wherein R represents one of H, C1-C12 alkyl, substituent or unsubstituted C6-C32 aryl, and substituted or unsubstituted C5-C32 heterocyclic aryl; Y represents one of S or O, and the heterocyclic aryl contains at least one heteroatom selected from O, S and N. The compound containing the azocine structure is used as a luminescent layer main body material of an organic electroluminescent device. Herein, the compound containing the azocine structure is adopted as the main material of the light-emitting layer, so that the light-emitting efficiency and the service life characteristic of the prepared OLED organic light-emitting device are significantly improved, the stability is excellent, and the organic light-emitting device prepared from the compound containing the azocine structure can be applied to the OLED device industry with high practicality, and has good application prospects.

Description

technical field [0001] The invention relates to a compound containing an azocine structure and its application, and belongs to the technical field of organic electroluminescent devices. Background technique [0002] Organic light-emitting diodes (OLED: Organic light Emission Diodes) have attracted attention from all walks of life due to their advantages such as flexibility, light weight, wide viewing angle, fast response, high color saturation, active light emission, thin thickness and low power consumption. extensive attention. Although OLED display technology has been extensively developed since it came out in 1987, there are still many problems to be solved urgently in order to meet people's requirements for higher performance and better effects of displays. For example, the poor luminous efficiency, poor stability and short life of OLED devices are one of the problems. [0003] OLED is a device that can actively emit light under an external driving voltage. The OLED de...

Claims

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Application Information

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IPC IPC(8): C07D491/06C07D495/06C07D519/00H01L51/54H01L51/50
CPCC07D491/06C07D495/06C07D519/00H10K85/622H10K85/615H10K85/624H10K85/631H10K85/654H10K85/657H10K85/6576H10K85/6572H10K50/11Y02E10/549
Inventor 李海艳柳佳欣曲江磊郭俊康李燕藏
Owner 烟台九目化学股份有限公司
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