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A class of luminescent materials containing polar substituted naphthoindenecarbazole units and their preparation and application

A polar substituent, naphthoindene carbazole technology, applied in the field of organic optoelectronics, can solve problems such as low lifespan, high price, and limited use

Active Publication Date: 2021-03-16
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, phosphorescent materials have attracted widespread attention due to their high quantum efficiency and luminous efficiency. However, phosphorescent materials are expensive and have low lifetime due to the heavy metal content, which restricts their use in OLED devices.

Method used

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  • A class of luminescent materials containing polar substituted naphthoindenecarbazole units and their preparation and application
  • A class of luminescent materials containing polar substituted naphthoindenecarbazole units and their preparation and application
  • A class of luminescent materials containing polar substituted naphthoindenecarbazole units and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Preparation of 2,7-dibromo-N-(2-hydroxyethyl)carbazole

[0057] In a 500mL there-necked flask, add 2-bromocarbazole (16.25g, 50mmol), an aqueous solution of potassium hydroxide (19.5g / 20ml deionized water, 0.5mol), benzyltriethylammonium chloride (1.61g, 5mmol) ), 200 mL of dimethyl sulfoxide, and stirred for 0.5 h under the protection of inert gas. 2-Bromoethanol (10.6 g, 60 mmol) was added dropwise. The reaction was stopped for 6 hours, extracted with ether, the organic phase was washed three times with saturated aqueous sodium chloride solution, the organic phase was collected, concentrated, and separated by column chromatography, using pure petroleum ether as the eluent to obtain a white solid with a yield of 88 %. 1 H NMR, 13 The results of CNMR, MS and elemental analysis show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

[0058]

Embodiment 2

[0059] Example 2: Preparation of 1-bromo-2 naphthoyl chloride

[0060] Under argon atmosphere, 1-bromo-2-naphthoic acid (9.00g, 35.85mmol) was dissolved in 80ml of N,N-dimethylformamide, and 20ml of thionyl chloride was added dropwise to the reaction solution, and at room temperature After stirring for 12 hours, the reaction was stopped, quenched with water, extracted with dichloromethane and dried with anhydrous magnesium sulfate. After the solution was concentrated, a khaki solid was obtained, which was purified by silica gel column chromatography and mixed with petroleum ether / dichloromethane. Solvent (3 / 1, v / v) as eluent gave a white solid in 75% yield. 1 HNMR, 13 The results of CNMR, MS and elemental analysis show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

[0061]

Embodiment 3

[0062] Example 3: Preparation of methyl 1-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-2-naphthoyl chloride

[0063] Under an argon atmosphere, 1-bromo-2-naphthoyl chloride (10.2 g, 37.7 mmol) was dissolved in 180 mL of purified THF, and 23.5 mL of 2.4 molL-1 of n-butyllithium was gradually added dropwise at -78 °C, After reacting for 2 hours, 12.6 g of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added, and the reaction was continued at -78°C for 1 hour, and then The temperature was raised to room temperature and reacted for 24 hours; the reaction mixture was poured into water, extracted with ethyl acetate, the organic layer was completely washed with brine, and dried over anhydrous magnesium sulfate; after the solution was concentrated, a pale yellow viscous crude product was obtained, which was passed through silica gel It was purified by column chromatography, and a mixed solvent of petroleum ether and ethyl acetate (6 / 1, v / v) was used as the eluent to obtain a wh...

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Abstract

The invention belongs to the field of organic photoelectric technology, and discloses a preparation method and application of a kind of luminescent material containing a polar substituent group naphthoindene carbazole unit. The luminescent material has the structure shown below. The present invention takes the naphthoindene carbazole unit containing the polar substituting group as the core, and obtains the naphthoindene carbazole containing the polar substituting group by selecting units with electron transport properties. Centered luminescent material. The chemical stability and chemical modification of the naphthoindene carbazole unit are strong, and a variety of chemical reactions can occur; the existence of the lone pair of electrons on the nitrogen atom endows the naphthoindene carbazole unit with better hole injection and transport properties; It has good planarity and high fluorescence quantum efficiency, which is conducive to improving the photoelectric performance of the material. Such materials are soluble in polar solvents such as methanol, DMF, DMSO, and water. The luminescent material prepared in the present invention can be prepared into a luminescent layer of a light-emitting diode through solution processing techniques such as spin coating, ink-jet printing, or printing and film formation.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and particularly relates to a preparation method and application of a class of luminescent materials containing a polar substituted group naphthoindenecarbazole unit. Background technique [0002] Compared with liquid crystal displays (LCDs), organic electroluminescent diodes (OLEDs) have attracted extensive attention from scientific research institutions and industries due to their wide viewing angle, active light emission, low operating voltage, ultra-thinness, flexible fabrication, and low power consumption. . At present, OLEDs displays have been widely used in mobile phone screens, and large-area OLED TVs have been developed and put into the market. However, OLEDs are expensive and other disadvantages, which limit the widespread and large-area use of OLEDs. Therefore, the development of new light-emitting materials, the improvement of the device fabrication process level and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/94C07D403/14C07D409/14C07F9/6558C09K11/06H01L51/54
CPCC09K11/06C07D209/94C07D403/14C07D409/14C07F9/65586C09K2211/1029C09K2211/1014C09K2211/1011C09K2211/1007C09K2211/1059C09K2211/1044C09K2211/1092H10K85/626H10K85/654H10K85/6574H10K85/6572
Inventor 应磊胡黎文黄飞曹镛
Owner 东莞伏安光电科技有限公司
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