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S,S-dioxo-dibenzothiophene and phenanthroimidazole based small molecule and application thereof in electroluminescent devices

A technology of dibenzothiophene and phenanthroimidazole, which is applied in the field of organic photoelectric materials, can solve the problems of failure to attract widespread attention and high device driving voltage, and achieve good hole and electron injection and transport capabilities, good thermal stability, Effect of High Fluorescence Quantum Yield

Active Publication Date: 2020-06-23
CHINA PETROLEUM & CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

OLED-related research can be traced back to the 1960s. In 1963, Professor Pope of New York University discovered the electroluminescence phenomenon of organic molecular single crystal anthracene for the first time, and then some single crystal structure materials have electroluminescence properties. However, due to the high driving voltage of the device at that time, it failed to attract widespread attention

Method used

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  • S,S-dioxo-dibenzothiophene and phenanthroimidazole based small molecule and application thereof in electroluminescent devices
  • S,S-dioxo-dibenzothiophene and phenanthroimidazole based small molecule and application thereof in electroluminescent devices
  • S,S-dioxo-dibenzothiophene and phenanthroimidazole based small molecule and application thereof in electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of compound M1

[0025] The structural formula and synthetic route of compound M1 are shown below, and the specific synthetic method is as follows

[0026]

[0027] (1) Synthesis of compound 1

[0028] Dissolve dibenzothiophene (10 mmol) in 100 mL of anhydrous tetrahydrofuran, cool to -78°C, add n-butyllithium solution (concentration: 2M, 5 mL) dropwise, raise to 0°C and stir for 2 hours after the addition is complete. Then the temperature was lowered to -78°C, 1,2-dibromoethane (15 mmol) was added to the reaction solution, and then the mixture was naturally raised to room temperature for 12 hours. After the reaction was completed, the reaction was quenched with 2 ml of deionized water, and the tetrahydrofuran was distilled and spin-dried under reduced pressure to obtain a crude product. Recrystallization with tetrahydrofuran / ethanol mixed solvent gave a white solid product with a yield of 60%.

[0029] (2) Synthesis of compound 2

[0030] Compound 2 ...

Embodiment 2

[0038] Preparation of compound M2

[0039] The structural formula and synthetic route of compound M2 are shown below, and the specific synthetic method is as follows

[0040]

[0041] (1) Synthesis of compound 5

[0042] Under nitrogen protection, phenanthrenequinone (10mmol), p-bromobenzaldehyde (10mmol) and aniline (10mmol) were added to 90ml of acetic acid, and heated to reflux for 24 hours. After cooling to room temperature and standing still, suction filtration was performed, and the filter residue was washed with ethanol three times to obtain a crude product. Recrystallization with tetrahydrofuran / ethanol mixed solvent gave a white solid product with a yield of 89%.

[0043] (2) Synthesis of compound 6

[0044] In a nitrogen atmosphere, reactant 5 (10mmol), biboronic acid pinacol ester (12mmol), potassium acetate (10mmol), Pd(dppf)Cl 2 (0.5mmol) was added to the reaction and dissolved with 100mL 1,4-dioxane, heated to 80°C and reacted for 12 hours. After the reacti...

Embodiment 3

[0048] Preparation of compound M3

[0049] The structural formula and synthetic route of compound M3 are shown below, and the specific synthetic method is as follows

[0050]

[0051] (1) Synthesis of Compound 7

[0052] Add S,S-dioxy-dibenzothiophene (10mmol) and concentrated sulfuric acid (50ml) into a 100ml two-necked bottle, and add N-bromosuccinyl in three batches under nitrogen protection and dark conditions. Amine (10 mmol), stirred at room temperature for 24 hours. The reaction solution was slowly poured into 1000ml of ice water, filtered, and the filter residue was washed three times with distilled water, and then washed three times with ethanol. The crude product was filtered and recrystallized three times with chlorobenzene to obtain a white solid with a yield of 66%. 1 H NMR, 13 The results of C NMR, MS and elemental analysis showed that the obtained compound was the target product.

[0053] (2) Synthesis of compound M3

[0054] Under the protection of nit...

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Abstract

The invention discloses an S,S-dioxo-dibenzothiophene and phenanthroimidazole based small molecule and application thereof in electroluminescent devices. Phenanthroimidazole is used as a donor unit, S,S-dioxo-dibenzothiophene is used as an acceptor unit, and a novel donor-acceptor type blue fluorescent molecule is constructed. The molecule has the characteristics of S,S-dioxo-dibenzothiophene suchas wide band gap, high fluorescence quantum yield, strong electron affinity, high electron mobility, and also has the characteristics of phenanthroimidazole such as large conjugate rigid structure, bipolar transmission, and the like. The molecule has an asymmetric structure, and can inhibit molecular aggregation and reduce exciton quenching. In addition, the emission spectrum can be adjusted by changing the connection sites of the two units. The small molecule can be used for preparing high-efficiency blue light organic electroluminescent devices with different emission wavelengths.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a class of small molecules based on S,S-dioxo-dibenzothiophene and phenanthroimidazole and their application in electroluminescent devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted extensive attention due to their advantages of flexibility, active light emission, high efficiency, low-voltage drive, and easy fabrication of large-area devices. OLED-related research can be traced back to the 1960s. In 1963, Professor Pope of New York University discovered the electroluminescence phenomenon of organic molecular single crystal anthracene for the first time, and then some single crystal structure materials have electroluminescence properties. However, due to the high driving voltage of the device at that time, it failed to attract widespread attention. It wasn't until 1987 that Deng Qingyun and others from Kodak Company...

Claims

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Application Information

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IPC IPC(8): C07D409/10C09K11/06H01L51/50H01L51/54
CPCC07D409/10C09K11/06C09K2211/1007C09K2211/1044C09K2211/1092H10K85/6576H10K85/6572H10K50/11Y02E10/549
Inventor 应磊彭沣郭婷彭俊彪曹镛
Owner CHINA PETROLEUM & CHEM CORP
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