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Soluble branch substituted anthracene molecule blue material as well as preparation method and uses thereof

A blue light material, soluble technology, applied in the direction of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., to achieve the effect of convenient purification, simple synthesis route and simple synthesis

Inactive Publication Date: 2008-06-18
GUANG ZHOU NEW VISION OPTO ELECTRONICS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, to make commercial light-emitting devices, there are still some important challenges, including material external quantum efficiency (EQE), operating voltage (power consumption), luminous color purity and long-term stability, etc. must be re-optimized.

Method used

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  • Soluble branch substituted anthracene molecule blue material as well as preparation method and uses thereof
  • Soluble branch substituted anthracene molecule blue material as well as preparation method and uses thereof
  • Soluble branch substituted anthracene molecule blue material as well as preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1,2,4, the preparation of 6-tribromoiodobenzene:

[0033] The mechanism of the reaction is as follows:

[0034]

[0035] Pour 2,4,6-tribromoaniline (46.95g, 142mmol) into a three-necked flask under ice-salt bath conditions, measure concentrated sulfuric acid (13.95g, 7.62mL, 142mmol), and then quickly dropwise add it into the flask, Mechanical stirring. Weigh sodium nitrite (14.73g, 213mmol) and dissolve it in 100mL of distilled water, pour it into the dropping funnel, start to add it slowly when the temperature drops below -5°C, control the temperature not to exceed 5°C and stir for 1h after the addition is completed , Potassium iodide (47.25g, 282mmol) was dissolved in 100ml of distilled water, poured into the dropping funnel, temperature controlled at 0-5°C and slowly added dropwise with enhanced stirring, and stirred for 30min after the dropwise addition was completed. Pour the mixed liquid into 300mL of NaHSO 3 After stirring in aqueous solution, C...

Embodiment 2

[0036] Embodiment 2,3, the preparation of 5-two p-tert-butylphenylbromobenzene:

[0037] A 500 mL three-neck flask was exhausted with Ar for 30 min, then magnesium powder (11.1 g, 468.45 mmol), iodine crystals (3-4 grains), THF (200 mL) were added, and stirred. Dilute p-tert-butylbromobenzene (89.73 g, 416.4 mmol) with 50 mL of THF and pour it into a constant pressure dropping funnel, and protect it with Ar gas. Slowly add p-tert-butylbromobenzene dropwise to the flask, and heat the flask with a hair dryer until the brown color of the solution fades and boils. After the dropwise addition, the oil bath was refluxed for 2h to obtain the Grignard reagent. Then the Grignard reagent was transferred to a 1L three-necked flask, and 2,4,6-tribromoiodobenzene (45.87g, 104.1mmol) was added to a constant pressure dropping funnel and dissolved with 150mL of THF, then slowly added dropwise to in the flask. Continue to stir for 1h after the dropwise addition, and then heat to reflux for ...

Embodiment 3

[0041] Example 3, Preparation of 3,5-di-p-tert-butylphenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaboryl)benzene:

[0042]

[0043] Dissolve 3,5-di-tert-butylphenyl-1-bromobenzene (4.21 g, 10 mmol) in 80 mL of dry tetrahydrofuran,

[0044] Protect with nitrogen gas, and cool to -78°C with liquid nitrogen / isopropanol. 2.5M n-BuLi (5.6 mL, 14 mmol) was slowly added dropwise into the reaction flask, and the mixture changed from colorless to yellow. After the dropwise addition, continue to stir at -78°C for 1 h, then add 4,4,5,5-tetramethyl-1,3,2-isopropanol borate (2.8 mL, 14 mmol) with a syringe, yellow Disappeared immediately, then naturally warmed to room temperature and stirred for 24h. The mixture was washed with distilled water and CH 2 Cl 2 Extracted 3 times, the oil layer was extracted with MgSO 4 dry.

[0045] A white solid was obtained by column chromatography.

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Abstract

The present invention discloses soluble branch substituted anthracene molecular blue light-emitting material and a preparation method and an application thereof. The anthracene molecular blue light-emitting material considers anthracene as a center, and soluble branch group Dendron and rigid group Ar1 are respectively accessed at the two ends of the anthracene to ensure that the prepared emitting material with an asymmetrical structure has certain solubility and can be purified by solution method. When the anthracene molecular blue light-emitting material is prepared, 9-bromoanthracene or 9-anthracene boric acid ester is used as reaction raw material, the soluble branch group Dendron is introduced by the palladium catalysis Suzuki coupling reaction, then N-bromosuccinimide is used for bromizing at 10-position of the anthracene to obtain an anthracene molecular bromide; the Ar1 is introduced into the obtained bromide or boric acid prepared from the bromide by the palladium catalysis Suzuki coupling reaction to obtain a target product. The material has the advantages of synthesis and purification and has important application prospect at electroluminescence display, illumination and laser.

Description

technical field [0001] The present invention relates to soluble dendritic substituted anthracene molecular materials. It specifically relates to an anthracene molecular blue-light material substituted by soluble dendrites and a preparation method thereof, and the invention also relates to the application of the molecular material in the preparation of light-emitting materials, light-emitting diodes, and lighting devices. Background technique [0002] In 1987, Tang and VanSlyke of Kodak Corporation of the United States prepared a small molecule organometallic complex octahydroxyquinoline aluminum (Alq 3 ) as a "sandwich" (anode / luminescent layer / cathode) thin-film electroluminescent device as a light-emitting layer, creating a fundamental and applied research on electroluminescence with extremely small molecules. During the past two decades, organic light-emitting diodes (OLEDs) have attracted considerable attention due to their potential applications in next-generation disp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/50
Inventor 朱旭辉赵利曹镛
Owner GUANG ZHOU NEW VISION OPTO ELECTRONICS TECH
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