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Anthracene derivatives, organic electroluminescent materials, light-emitting devices and consumer products

An anthracene derivative and carbon atom technology, applied in the field of organic electroluminescence, can solve the problems of reducing the quantum yield of blue light system, aggravating molecular fluorescence quenching, low luminescence quantum efficiency, etc., so as to improve internal quantum efficiency, improve solubility, Increase the effect of molecular steric hindrance

Active Publication Date: 2022-01-11
SHANGHAI BAYI SPACE ADVANCED MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, blue light materials still have the problems of low luminous quantum efficiency and poor color purity.
The main reason for this situation is that the blue light comes from the transition between energy levels with a wide energy gap, and organic compounds with wide band gaps have certain difficulties in molecular design, and secondly, there are strong blue light materials in the system. The π-π bond interaction has strong charge transfer characteristics, so that there are more non-radiative relaxation channels in the wide band gap, which intensifies the fluorescence quenching between molecules and reduces the quantum yield of the blue light system

Method used

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  • Anthracene derivatives, organic electroluminescent materials, light-emitting devices and consumer products
  • Anthracene derivatives, organic electroluminescent materials, light-emitting devices and consumer products
  • Anthracene derivatives, organic electroluminescent materials, light-emitting devices and consumer products

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Preparation of intermediate A1:

[0084] The preparation method of intermediate A1, comprises the steps:

[0085] Step 1: Preparation of Compound Int.-1

[0086]

[0087] Under the protection of nitrogen, 50.0mmol of o-iodobromobenzene was dissolved in 100mL of dry tetrahydrofuran, cooled to 0°C, 52.0mL of 1M isopropylmagnesium bromide THF solution was added dropwise, stirred for 1 hour, and 48.0mmol of 9H-Tribenzo[a,c,e][7]cycloann-9-one (CAS:68089-73-6) dissolved in THF solution, raised to room temperature and stirred for 2 hours, added 50mL of 2N dilute Hydrochloric acid aqueous solution was extracted with ethyl acetate, the organic phase was collected, dried, filtered, the filtrate was concentrated and dried under reduced pressure, separated and purified by silica gel column to obtain the intermediate Int.-1 with a yield of 94%.

[0088] The second step: the preparation of compound Int.-2

[0089]

[0090] Under the protection of nitrogen, dissolve 40.0mmol...

Embodiment 2

[0104] Preparation of compound CJHB761:

[0105]

[0106] Mix 15.0mmol of intermediate A1 with 60mL of toluene, and add 18.0mmol of (4-(2-naphthyl)phenyl)boronic acid, 54.0mmol of anhydrous sodium carbonate and 173.0mg of Pd(PPh 3 ) 4 Catalyst, then add 30mL of ethanol and 30mL of water, heat up to reflux and stir for 12 hours, cool to room temperature, filter, wash the filter cake with water and ethanol, separate and purify with silica gel column to obtain white solid CJHB761, yield 84%. EI-MS / FAB, m / e: 530.76, calculated: 530.20.

[0107] With reference to the above-mentioned synthetic method, the following compounds were prepared:

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

Embodiment 3

[0117] The preparation method of compound CJHB775 comprises the steps:

[0118] The first step: preparation of compound Int.-5

[0119]

[0120] Under the protection of nitrogen, 50.0mmol of A1 was dissolved in 120mL of dry THF, cooled to -100°C, 24mL of 2.5M n-butyllithium n-hexane solution was added dropwise, stirred for 30 minutes, and 75.0mmol of triisoborate was added dropwise. Butyl ester, stir for 30 minutes, heat up to -70°C for 1 hour, add dropwise 50 mL of 2N dilute hydrochloric acid aqueous solution, stir for 30 minutes, separate the organic phase, extract the aqueous phase with ethyl acetate, collect the organic phase, dry, and filter , the filtrate was concentrated and dried under reduced pressure, dispersed by adding petroleum ether, and filtered to obtain Int.-5 with a yield of 85%.

[0121] The second step: the preparation of compound CJHB775

[0122]

[0123] Mix 12.0mmol of intermediate Int.-5 with 60mL of toluene, and add 10.0mmol of 2-chloro-4,6-dip...

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Abstract

The invention relates to an anthracene derivative, an organic electroluminescent material, a light-emitting device and a consumer product. The anthracene derivative is a novel organic electroluminescent compound with a seven-membered ring non-planar structure formed by anthracene and biphenyl; wherein the seven-membered ring anthracene derivative increases molecular steric hindrance, hinders the generation of an organic intermolecular excitation-excitation complex, improves internal quantum efficiency, and has a shorter emission wavelength than existing compounds, thereby improving the efficiency and lifespan of an organic electroluminescent device comprising the compound; in addition, the compound improves the solubility in a solution and solves the problems of process productivity and cost of a conventional blue light emitting material.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to an anthracene derivative, an organic electroluminescence material, a light-emitting device and a consumer product. Background technique [0002] Most of the substances used in organic electroluminescent elements are pure organic substances or organometallic complexes that form complexes between organic substances and metals. According to the application, they can be divided into hole injectors, hole transporters, luminescent substances, and electron transporters. , electron injectants, etc. Here, organic substances with relatively low ionization energy are mainly used as hole injectors or hole transporters, and organic substances with relatively high electronegativity are mainly used as electron injectors or electron transporters. In addition, the substance used as the luminescence assisting layer preferably satisfies the following characteristics....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/62C07D213/16C07D307/77C07D307/91C07D235/18C07D471/04C07D405/04C07D251/24C07D239/26C07D239/74C07D239/70C07D241/42C07D241/38C07D263/57C07D221/10C07C255/50C07C211/61C07C211/54C07C211/58C07D209/86C07D235/02C09K11/06H01L51/50H01L51/54
CPCC07C13/62C07D213/16C07D307/77C07D307/91C07D235/18C07D471/04C07D405/04C07D251/24C07D239/26C07D239/74C07D239/70C07D241/42C07D241/38C07D263/57C07D221/10C07C255/50C07C211/61C07C211/54C07C211/58C07D209/86C07D235/02C09K11/06C07C2603/54C07C2603/42C07C2603/26C09K2211/1029C09K2211/1033C09K2211/1088C09K2211/1044C09K2211/1014C09K2211/1011C09K2211/1074H10K85/624H10K85/622H10K85/636H10K85/633H10K85/615H10K85/631H10K85/654H10K85/6574H10K85/6572H10K85/657H10K50/16H10K50/11Y02E10/549
Inventor 曹建华张海威郭文龙边坤唐怡杰刘殿君王振宇何连贞
Owner SHANGHAI BAYI SPACE ADVANCED MATERIAL CO LTD
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