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Bipolar small molecular light-emitting material based on aromatic heterocyclo-2-S,S-dioxydibenzothiophene unit, and preparation method and application thereof

A technology of dioxydibenzothiophene and luminescent materials, applied in luminescent materials, electrical components, chemical instruments and methods, etc., to achieve the effects of balanced injection and transport, good electron and hole transport performance, and good solubility

Active Publication Date: 2017-06-20
东莞阿尔达新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a bipolar small molecule luminescent material based on aromatic heterocycle-2-S,S-dioxodibenzothiophene unit in view of the problems faced by organic light-emitting diodes (OLEDs) at present.

Method used

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  • Bipolar small molecular light-emitting material based on aromatic heterocyclo-2-S,S-dioxydibenzothiophene unit, and preparation method and application thereof
  • Bipolar small molecular light-emitting material based on aromatic heterocyclo-2-S,S-dioxydibenzothiophene unit, and preparation method and application thereof
  • Bipolar small molecular light-emitting material based on aromatic heterocyclo-2-S,S-dioxydibenzothiophene unit, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Methyl 1-bromo-2-quinoxalinecarboxylate

[0036] Under an argon atmosphere, add 1-bromo-2-quinoxalinecarboxylic acid (10g, 39.83mmol) into a two-necked flask, add 100mL of methanol, then add concentrated sulfuric acid (39.06mg, 398.29umol) dropwise, and heat to 110 °C, reacted for 18h. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a white solid crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / dichloromethane=3 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid with a yield of 85%. . 1 H NMR, 13 CNMR, MS and elemental analysis results show that the compound obtained is the target product, and its chemical reaction equation is as follows:

[0037]

Embodiment 2

[0039] Preparation of 2-bromothiofluorene

[0040] Under an argon atmosphere, add thiofluorene (20g, 108.54mmol) into a 250ml two-necked bottle, then add 100ml of chloroform to dissolve completely, add iodine (275.39mg, 1.09mmol), drop by drop under the condition of avoiding light Add liquid bromine (38.16g, 108.54mmol), the reaction solution was stirred under ice bath for 2 hours, then stirred at room temperature for 2 hours, adding saturated sodium bisulfite to quench the liquid bromine, the reaction mixture was poured into water, washed with acetic acid Extracted with ethyl ester, the organic layer was washed completely with brine, and dried over anhydrous magnesium sulfate. After the solution was concentrated, a crude white solid was obtained, which was then recrystallized from chloroform with a yield of 85%. 1 HNMR, 13CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:

[0041]...

Embodiment 3

[0043] 2-boronate thiofluorene

[0044] Under an argon atmosphere, 2-bromothiofluorene (10 g, 29.24 mmol) was dissolved in 180 mL of refined tetrahydrofuran (THF), and 1.6 mol L of -1 28mL of n-butyllithium, reacted for 2 hours, then quickly added 25mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane, at -78℃ The reaction was continued for 1 hour, and the temperature was slowly raised to room temperature for 24 hours. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a light yellow viscous crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / ethyl acetate=20 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid, the product rate of 70%. 1 H NMR and GC-MASS tests showed that it was the target product. Its che...

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Abstract

The invention discloses a bipolar small molecular light-emitting material based on an aromatic heterocyclo-2-S,S-dioxydibenzothiophene unit, and a preparation method and application thereof. The preparation method comprises the following step: performing Suzuki coupling reaction on an aromatic heterocyclo-2-S,S-dioxydibenzothiophene monomer and a borate monomer containing an Ar structure to obtain the bipolar small molecular light-emitting material based on an aromatic heterocyclo-2-S,S-dioxydibenzothiophene unit. The bipolar small molecular light-emitting material disclosed by the invention has solubility, film forming property and film morphology stability, also has favorable electron and hole transmission performance, and can balance carrier injection and transmission to realize effective compounding of more excitons; a light-emitting layer based on the material can avoid the phenomenon of mixing with a hole / electron transmission layer interface, thereby improving the light-emitting efficiency of a device; and the light-emitting layer based on the material dose not need to be subjected to annealing treatment during preparation of the electroluminescent device, thereby ensuring that the preparation process is simple.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a bipolar small molecule luminescent material based on an aromatic heterocycle-2-S,S-dioxodibenzothiophene unit and its preparation method and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted widespread attention due to their high efficiency, low-voltage drive, and ease of large-area fabrication. The research on OLED began in the 1950s. Until 1987, Dr. Qingyun Deng of Kodak Company of the United States developed an OLED device with a luminous brightness of 1000cdm driven by a 10V DC voltage using a sandwich device structure. -2 , so that OLED has achieved an epoch-making development. [0003] The OLED device consists of a cathode, an anode, and an organic layer in the middle. The organic layer generally includes an electron transport layer, a light-emitting layer, and a hole transport layer. First, electr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D495/04H01L51/54
CPCC09K11/06C07D495/04C09K2211/1044C09K2211/1092H10K85/631H10K85/6572H10K85/657
Inventor 应磊赵森郭婷杨伟彭俊彪曹镛
Owner 东莞阿尔达新材料科技有限公司
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