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Bipolar small molecule luminescent material based on aromatic heterocyclo-2-s,s-dioxodibenzothiophene unit and its preparation method and application

A technology of dioxydibenzothiophene and -2-S, which is applied in the field of bipolar small molecule light-emitting materials and its preparation, achieves the effects of simple preparation process, balanced injection and transmission, and improved efficiency of materials and devices

Active Publication Date: 2019-06-18
东莞阿尔达新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 molecule luminescent material based on aromatic heterocyclo-2-s,s-dioxodibenzothiophene unit and its preparation method and application
  • Bipolar small molecule luminescent material based on aromatic heterocyclo-2-s,s-dioxodibenzothiophene unit and its preparation method and application
  • Bipolar small molecule luminescent material based on aromatic heterocyclo-2-s,s-dioxodibenzothiophene unit and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0034] Methyl 1-bromo-2-quinoxalinecarboxylate

[0035] 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:

[0036]

Embodiment 2

[0038] Preparation of 2-bromothiofluorene

[0039] 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:

[0040]...

Embodiment 3

[0042] 2-boronate thiofluorene

[0043] 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 molecule luminescent material based on an aromatic heterocycle and-2-S,S-dioxodibenzothiophene unit, as well as a preparation method and application thereof. In the present invention, after the aromatic heterocyclic a-2-S, S-dioxodibenzothiophene monomer and the borate monomer containing Ar structure are reacted through Suzuki coupling, the aromatic heterocyclic a-2 based ‑S, S‑Dioxydibenzothiophene unit bipolar small molecule luminescent material. The bipolar small-molecule luminescent material of the present invention has good solubility, film-forming property and thin-film morphology stability, and has good electron and hole transport properties, and can balance the injection and transport of carriers, so that more The excitons are effectively recombined, and the light-emitting layer based on the material can avoid the mixing phenomenon with the interface of the hole / electron transport layer, thereby improving the luminous efficiency of the device; the light-emitting layer based on the material of the present invention does not need to be annealed when preparing an electroluminescent device processing, making the preparation process 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 Patents(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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