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Benzothieno [3, 2-b] benzothiophene-like hole transport material and preparation method and application thereof

A hole transport material, 2-b technology, used in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problems of crystallization, affecting the performance of organic light-emitting diodes, etc. The effect of hole mobility and stable performance

Active Publication Date: 2021-06-25
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a benzothieno[3,2-b]benzothiophene-like hole-transport material and its preparation method and application, aiming to solve the problem of existing hole-transport materials. NPB has precipitation or crystallization, which seriously affects the performance of organic light-emitting diodes

Method used

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  • Benzothieno [3, 2-b] benzothiophene-like hole transport material and preparation method and application thereof
  • Benzothieno [3, 2-b] benzothiophene-like hole transport material and preparation method and application thereof
  • Benzothieno [3, 2-b] benzothiophene-like hole transport material and preparation method and application thereof

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preparation example Construction

[0050] An embodiment of the present invention provides a method for preparing a hole transport material based on benzo[4,5]thieno[3,2-b]benzofuran as described above, which includes the steps of:

[0051] BTBF-Br is provided, and the BTBF-Br is reacted to obtain the target product;

[0052]

[0053] An embodiment of the present invention provides a method for preparing a hole transport material based on benzo[b]benzo[4,5]thieno[2,3-f]benzofuran as described above, which includes the steps of:

[0054] BTBFB-Br is provided, and the target product is obtained by reacting the BTBFB-Br;

[0055]

[0056] The hole transport material based on benzo[4,5]thieno[3,2-b]benzofuran described in the embodiment of the present invention is applied in an organic light emitting diode.

[0057] The hole transport material based on benzo[b]benzo[4,5]thieno[2,3-f]benzofuran described in the embodiment of the present invention is applied in an organic light emitting diode.

[0058] An embo...

Embodiment 1

[0062] 1. The preparation steps of BTBF-Br are as follows:

[0063] (1) Dissolve benzothiophene (25mmol) and N-bromosuccinimide (NBS) (30mmol) in CHCl at 0°C 3 (200mL) and CH 3 A mixture of COOH (200 mL) was stirred at 0° C. for 4 h, and then the reaction was continued at room temperature for 24 h. After the reaction was complete, saturated sodium thiosulfate solution (100 ml) and saturated sodium carbonate (100 ml) were added to remove excess NBS and acetic acid. The mixture was then washed with water (100 mL) and extracted with dichloromethane (DCM). After rotary evaporation of the solvent, the residual crude product was purified by column chromatography on 200-300 mesh silica gel using petroleum ether (PE) as the eluent to obtain compound 1 (yield 98.6%);

[0064]

[0065] (2) Compound 1 (8.4mmol) was added to CHCl 3 (120mL), and CF 3 COOH (120 mL) was added dropwise to the mixture, which was then stirred at room temperature for 6 minutes. then H 2 o 2 (10 g) was...

Embodiment 2

[0081] 1. The preparation steps of BTBFB-Br are as follows:

[0082] (1) Add compound 6 (10mmol) and dibromophenol (12mmol) to a mixed solution of toluene (200mL) and ethanol (100mL), and then add 2M K 2 CO 3 Aqueous solution (30mL) and Pd(PPh 3 ) 4 (0.02mmol) was stirred at 100°C for 24h; after the reaction was completed, it was filtered, extracted with DCM, dried and concentrated, and subjected to silica gel column chromatography to obtain compound 7 (yield 84.9%);

[0083]

[0084] (2) Under a nitrogen atmosphere, add compound 7 (5mmol) and p-toluenesulfonic acid (8mmol) into toluene (200mL), and stir at 100°C for 24h; after the reaction, add saturated Na 2 CO 3 The aqueous solution was quenched, the liquid was extracted and separated with ethyl acetate, dried and concentrated, and the compound BTBFB-Br was obtained by silica gel column chromatography (yield 79.8%);

[0085]

[0086]2. A hole-transporting material based on benzo[b]benzo[4,5]thieno[2,3-f]benzofura...

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Abstract

The invention discloses a benzothieno [3, 2-b] benzothiophene-like hole transport material as well as a preparation method and application thereof. According to the invention, a benzo five-membered ring [3, 2-b] benzo five-membered ring (BXBY)-based hole transport material and a benzo [b] benzo [4, 5] five-membered ring [2, 3-f] benzo five-membered ring (BXBYB)-based hole transport material which have similar structures are designed and synthesized, and are applied to organic light emitting diodes as hole transport layer materials. The hole transport materials with the two structures have excellent performance and stable performance, and the performance and the service life of the organic light emitting diode can be greatly improved and prolonged. The organic light-emitting diode with the structure made of the hole transport material has the performance far better than that of the organic light-emitting diode in the market.

Description

technical field [0001] The invention relates to the technical field of organic semiconductor materials, in particular to a benzothieno[3,2-b]benzothiophene-like hole-transporting material and a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have received extensive attention from academia and industry worldwide since their breakthrough in 1987. Organic light-emitting diodes have the advantages of low cost, easy manufacturing, wide viewing angle, wide operating temperature, adjustable color temperature, high resolution, clear image, good contrast, low power consumption, high transparency, light weight, and flexibility, making them the most Popular display and lighting technologies. Organic light-emitting diodes with long lifetime and high power efficiency are in great demand in the lighting and display markets. The organic light emitting diode device is a multi-layer thin film structure, which is respectively a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04H01L51/54H01L51/50
CPCC07D495/04H10K85/636H10K85/633H10K85/657H10K50/15
Inventor 孟鸿王江峰贺耀武
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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