Diazabenzofluoranthene compound as well as preparation method and application thereof

A technology of diazofluoranthene and benzofluoranthene, which is applied in the field of diazofluoranthene compounds and their preparation, can solve problems such as narrow spectral range, achieve wide spectral range, good application prospects, and significant economical value effect

Active Publication Date: 2021-11-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, most of the organic light-emitting materials are blue and green light materials, and there are few researches on orange / red materials. Acceptor as the core, synthesize four organic thermally induced delayed fluorescent materials, which have good thermal stability and adjustable luminous color, and can be used for orange / red TADF OLED emitters, but their spectral range (580-620nm) is narrow

Method used

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  • Diazabenzofluoranthene compound as well as preparation method and application thereof
  • Diazabenzofluoranthene compound as well as preparation method and application thereof
  • Diazabenzofluoranthene compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] A diazobenzofluoranthene compound, its structural formula is as follows:

[0056]

[0057] The synthetic route of this compound is as follows figure 1 Shown, its preparation method comprises the steps:

[0058] Preparation of S1.1,4-dibromobenzene-2,3-difluoro-5,6-dinitrobenzene:

[0059] Put the three-necked flask (250mL), spherical condenser, atmospheric dropping funnel, glass stopper and stirring bar into an oven, and dry at 100°C for 30min. Take out the dried three-necked flask, add 50mL trifluoromethanesulfonic acid dropwise, then slowly add 2.5mL fuming nitric acid, stir in ice bath for 30min; then, add 18.4mmol of 1,4-dibromo-2 , 5g of 3-difluorobenzene, stirred at room temperature for 2h, cooled the mixture to 0°C, then slowly added 2.5mL of fuming nitric acid, heated to 70°C and reacted for 30h; finally, added sodium hydroxide under ice bath conditions to adjust the pH The value was adjusted to 7, filtered and collected to obtain a light yellow solid with...

Embodiment 2

[0074] A preparation method of a diazobenzofluoranthene compound, comprising the steps of:

[0075] In step S1, the molar ratio of 1,4-dibromo-2,3-difluorobenzene, fuming nitric acid and trifluoromethanesulfonic acid is 1:9:70, the nitration reaction temperature is 70°C, and the reaction time is 24h, the product Rate is 44%, and others are with embodiment 1.

[0076] In step S2, the molar ratio of 1,4-dibromobenzene-2,3-difluoro-5,6-dinitrobenzene, iron powder and acetic acid is 1:15:175, the reduction reaction temperature is 40°C, and the reaction time is Be 8h, productive rate is 70%, other is with embodiment 1.

[0077] In step S3, the molar ratio of 3,6-dibromobenzene-4,5-difluoro-1,2-phenylenediamine to acenaphthenequinone compound is 1:1, the condensation reaction temperature is 100°C, and the reaction time is 16h. Productive rate is 70%, other is with embodiment 1.

[0078] Intermediate α, basic salt, palladium-containing coupling agent and electron donor group D in ...

Embodiment 3

[0081] A preparation method of a diazobenzofluoranthene compound, comprising the steps of:

[0082] In step S1, the molar ratio of 1,4-dibromo-2,3-difluorobenzene, fuming nitric acid and trifluoromethanesulfonic acid is 1:8:45, the nitration reaction temperature is 50°C, and the reaction time is 36h, the product Rate is 72%, and others are with embodiment 1.

[0083] In step S2, the molar ratio of 1,4-dibromobenzene-2,3-difluoro-5,6-dinitrobenzene, iron powder and acetic acid is 1:20:150, the reduction reaction temperature is 60°C, and the reaction time is Be 6h, productive rate is 80%, other is with embodiment 1.

[0084] In step S3, the molar ratio of 3,6-dibromobenzene-4,5-difluoro-1,2-phenylenediamine to acenaphthenequinone compound is 1:1, the condensation reaction temperature is 125°C, and the reaction time is 8h. Productive rate is 75%, other is with embodiment 1.

[0085] Intermediate α, basic salt, palladium-containing coupling agent and electron donor group D in s...

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PUM

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Abstract

The invention discloses a diazabenzofluoranthene compound as well as a preparation method and application thereof. Pyrazine is taken as an electron withdrawing body, a plurality of different electron donors (D) are introduced, a charge transfer luminescent material with a D-A or D-pi-A donor-acceptor structure is formed, adjustable luminescent color in a wide spectral range (531-713nm) is realized, the highest fluorescence quantum yield can reach 96%, and the novel luminescent molecule is good in performance and low in cost, has remarkable economic value in the application aspects of preparation of luminescent materials, luminescent devices or intelligent materials and the like, and has good application prospects in the fields of full-color display and solid-state illumination.

Description

technical field [0001] The present invention relates to the technical field of organic luminescent materials, and more specifically, relates to a diazobenzofluoranthene compound and its preparation method and application. Background technique [0002] The technology of organic light-emitting materials used as organic light-emitting diodes (OLEDs) is widely used in flat panel displays, smart phones, and solid-state lighting. Thanks to the large-area and high-quality display and lighting, ultra-high resolution, and Significant advantages such as ultra-fast response speed and flexibility. It has great application potential in the fields of flat panel display, smart phone and solid-state lighting, and has attracted extensive attention from the global academic and industrial circles. [0003] At present, most of the organic light-emitting materials are blue and green light materials, and there are few researches on orange / red materials. The acceptor is the core, and four kinds ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C09K11/06
CPCC07D403/14C09K11/06C09K2211/1044C09K2211/1029
Inventor 刘博陈文铖霍延平张浩力籍少敏
Owner GUANGDONG UNIV OF TECH
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