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9,9'-spiral acridine-containing compound and preparation method and application thereof

A compound, the technology of spiroacridine, which is applied in the field of compounds containing 9,9'-spiroacridine and its preparation, can solve the problems of low triplet energy level, high degree of molecular conjugation, and difficulty in realizing triplet energy level difference, etc. , achieve high device efficiency, low singlet-triplet energy level difference, and improve the effect of exciton utilization

Inactive Publication Date: 2017-06-13
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In traditional organic light-emitting molecules, the interaction between the electron-donating unit and the electron-deficient unit is usually too strong, and the degree of conjugation of the molecule is too large, resulting in a lower triplet energy level, and it is difficult to achieve a smaller singlet-triplet energy level difference.

Method used

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  • 9,9'-spiral acridine-containing compound and preparation method and application thereof
  • 9,9'-spiral acridine-containing compound and preparation method and application thereof
  • 9,9'-spiral acridine-containing compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] step 1:

[0042] The preparation of (4-bromophenyl)-phenyl-carbamic acid tert-butyl ester, reaction formula is as follows:

[0043]

[0044] In a 1-liter single-necked flask, di-tert-butyl dicarbonate (BOC) (0.2mol, 43.6g) was added to 400ml of tetrahydrofuran at room temperature, and then p-N-(dibromophenyl)aniline (0.1mol , 24.8g), heated to reflux and stirred for 24 hours. The mixture was then poured into 1 L of water, and the product was extracted with dichloromethane. Dry the organic phase with anhydrous magnesium sulfate, remove the solvent after separation, and separate and purify with silica gel chromatography to obtain a colorless oily liquid (32.0 g, yield 92%).

[0045] Step 2:

[0046] The preparation of 10-((2-methoxyethoxy)methyl)-9(10H)acridone, the reaction formula is as follows:

[0047]

[0048]In a 500 ml three-necked flask, 9(10H) acridone (90 mmol, 17.55 g) was added to 200 ml of DMF, and then sodium hydride (120 mmol, about 5.8 g) with a ...

Embodiment 2

[0058] The preparation of compound S2, reaction formula is as follows:

[0059]

[0060] Add 10H,10'H-9,9'-spiroacridine (1.2 mmol, 0.42 g) and 4-(4-bromophenyl)-2,6-diphenylpyrimidine to the reaction flask under argon atmosphere (2.7mmol, 1.04g), 50ml of toluene as solvent, palladium acetate 60mg, tri-tert-butylphosphine (0.5mmol, 0.11g), and 0.48g of sodium tert-butoxide. The reaction was stirred under reflux for 24 hours. After cooling, the mixture was poured into 200 ml of water, and the product was extracted with dichloromethane. Dry the organic phase with anhydrous magnesium sulfate, remove the solvent after separation, and separate and purify with silica gel chromatography to obtain a light yellow solid. After drying, the product was sublimed under vacuum to obtain a high-purity product (0.82 g, yield 71%).

Embodiment 3

[0062] The preparation of compound S3, reaction formula is as follows:

[0063]

[0064] Add 10H,10'H-9,9'-spiroacridine (1.2 mmol, 0.42 g) and 4'-(4-bromophenyl)-2,2';6' to the reaction flask under argon atmosphere , 2 "-terpyridine (2.8mmol, 1.08g), 50 milliliters of toluene as solvent, 60 milligrams of palladium acetate, tri-tert-butylphosphine (0.5 mmol, 0.11 g), and 0.48 gram of sodium tert-butoxide. Stir under reflux Reacted for 24 hours, after cooling, the mixed solution was poured into 200 milliliters of water, and product was extracted with dichloromethane. Anhydrous magnesium sulfate dried the organic phase, separated and removed the solvent, separated and purified with silica gel chromatography to obtain a light-colored solid. After drying, the Sublimation under vacuum gave a high-purity product (0.68 g, yield 59%).

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Abstract

The invention discloses a 9,9'-spiral acridine-containing compound. 9,9'-spiral acridine is taken as a core and the 9,9'-spiral acridine is combined with peripheral electrophilic Ar and Ar' units. The invention further discloses a preparation method of the 9,9'-spiral acridine-containing compound. The 9,9'-spiral acridine-containing compound is obtained through selecting different halogen-substituted Ar unit and Ar' unit, carrying out Buchwald-Hartwig coupled reaction on 10H, 10'H-9,9'-spiral acridine, carrying out copper-catalyzed aryl halide amination reaction or carrying out nucleophilic substitution reaction under a strong alkaline condition. The invention further discloses an application of the 9,9'-spiral acridine-containing compound. The 9,9'-spiral acridine-containing compound has high fluorescence and certain conductivity, and can be used for fabricating a light-emitting layer of an organic light-emitting diode as a luminous body.

Description

technical field [0001] The invention relates to the technical field of electroluminescence materials, in particular to a compound containing 9,9'-spiroacridine and its preparation method and application. Background technique [0002] In the past two decades, organic light-emitting diodes (OLEDs) have broad application prospects due to their high efficiency, low-voltage drive, easy large-area preparation and full-color display, and have attracted widespread attention. The research began in the 1950s, and until 1987, Dr. Deng Qingyun of Kodak Company of the United States adopted a sandwich device structure in the patent US4356429, and the OLED device developed by the 10V DC voltage drive had a luminous brightness of 1000cd / m 2 , so that OLED has achieved an epoch-making development. [0003] Organic electroluminescence is mainly divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet excitons and triplet ...

Claims

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Application Information

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IPC IPC(8): C07D471/10C09K11/06H01L51/54
CPCC09K11/06C07D471/10C09K2211/1044C09K2211/1059C09K2211/1029C09K2211/1092H10K85/657H10K85/6576H10K85/6572
Inventor 苏仕健刘明城户淳二笹部久宏小松龙太郎
Owner SOUTH CHINA UNIV OF TECH
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