A small molecule hole transport material based on spiro-bisthioxanthene and its preparation method and application

A technology of hole transport material and thioxanthene, which is applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problem that organic transport small molecule materials are rarely reported, and improve the carrier transport characteristics. Effect

Active Publication Date: 2021-03-16
SOUTH CHINA INST OF COLLABORATIVE INNOVATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, although there have been many reports on hole transport materials for OLED devices, perovskite light-emitting devices, and quantum dot light-emitting devices, there are few reports on organic transport small molecule materials with a spiro-dithioxanthene structure as the core.

Method used

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  • A small molecule hole transport material based on spiro-bisthioxanthene and its preparation method and application
  • A small molecule hole transport material based on spiro-bisthioxanthene and its preparation method and application
  • A small molecule hole transport material based on spiro-bisthioxanthene and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of P1:

[0039]

[0040] Preparation of P1: In a low-temperature reaction flask, add compound 1 (1-bromo-2phenylmercaptobenzene, preparation method reference: Schopfer, U.; Schlapbach, A.A general palladium-catalysed synthesis of aromatic and heteroaromatic thioethers. Tetrahedron 2001,57 , 3069-3073.) (2.65g, 100mmol), dissolved in 60ml THF, protected by nitrogen gas, sealed the device, cooled to -78°C with liquid nitrogen, added dropwise butyllithium (1.6mol / L in hexanes , 70mL, 110mmol), keep warm for 40min, then add 2.2g of thioxanthone in THF (50mL) at one time, and react overnight at room temperature. After the reaction is complete, THF is removed with a rotary evaporator, extracted with dichloromethane, and the product alcohol M3 is separated by a column. The product M3 was added with 20ml of acetic acid and 1.5mL of hydrochloric acid, under nitrogen protection, stirred overnight at 80°C, and separated by column to obtain 22.0g o...

Embodiment 2

[0041] Embodiment 2: the preparation of P3

[0042] Synthesis of intermediate product M4

[0043]

[0044] The synthesis method of M4 is as in P1. Add compound 1 (2.65g, 100mmol) into a low-temperature reaction flask, dissolve it with 60ml THF, and protect it with nitrogen gas. After sealing the device, add liquid nitrogen to cool to -78°C, and add dimethicone dropwise within 30min. base lithium (1.6mol / L inhexanes, 70mL, 110mmol), keep warm for 40min, then add 2.21g of 3,7-dibromothioxanthone in THF (50mL) at one time, and react overnight at room temperature. After the reaction was complete, THF was removed with a rotary evaporator, extracted with dichloromethane, and the product alcohol was separated by a column. The product alcohol was added to 20ml of acetic acid and 1.5mL of hydrochloric acid, protected by nitrogen, stirred at 80°C overnight, and separated by column to obtain 0.83g of white solid with a yield of 81%. 1H NMR: 7.22 - 7.18 (m, 4H), 7.04 (dd, J = 11.7, 4...

Embodiment 3

[0047] Embodiment 3: the synthesis of P2

[0048] Synthesis of intermediate product M5

[0049]

[0050] The synthesis method of M5 is as in P1. Add compound 1 (2.65g, 100mmol) into a low-temperature reaction flask, dissolve it with 60ml THF, and protect it with nitrogen gas. After sealing the device, add liquid nitrogen to cool to -78°C, and add D Base lithium (1.6mol / L inhexanes, 70mL, 110mmol), keep warm for 40min, then add 1.86g of 3-bromothioxanthone in THF (60mL) at one time, and react overnight at room temperature. After the reaction was complete, THF was removed with a rotary evaporator, extracted with dichloromethane, and the product alcohol was separated by a column. The product alcohol was added to 20ml of acetic acid and 1.5mL of hydrochloric acid, protected by nitrogen, stirred at 80°C overnight, and separated by column to obtain 0.65g of white solid with a yield of 81%. The molecular weight of the final product obtained by mass spectrometry: 457.98. Element...

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PUM

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Abstract

The invention belongs to the field of organic electrochemistry, and discloses a hole-transporting material based on a spiro-bisthiaxanthene small molecule, a preparation method and an application thereof. The structure of this hole transport material is shown below P1n. The hole-transporting material uses the spiro-bisthiaxanthene nucleus as a skeleton unit, and the molecular weight, π-conjugation and energy-level structure properties of the material can be adjusted by changing the connecting units on both sides and the number thereof. The hole transport material has a single structure, a definite molecular weight, and good solubility and film-forming properties in common solvents. It can be used as a hole transport material in perovskite battery devices, thereby improving the performance of the device and for high-efficiency devices. Development has far-reaching implications.

Description

technical field [0001] The invention belongs to the field of organic electrochemistry, and in particular relates to a hole-transporting material based on a spiro-bisthiaxanthene small molecule, a preparation method and application thereof. Background technique [0002] In order to improve the efficiency and lifespan of OLED devices, perovskite light-emitting devices, and quantum dot light-emitting devices, compared with polymers, small hole-transporting molecules have fewer preparation steps, stable structures, and no disadvantages of polydispersity. more likely to be commercialized. The preparation of multilayer devices by evaporation or solution processing of small molecules has received great attention and great progress has been made. [0003] So far, although there have been many reports on hole transport materials for OLED devices, perovskite light-emitting devices, and quantum dot light-emitting devices, there are few reports on organic transport small molecule mater...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/10C07D519/00H01L51/50H01L51/54H01L51/42H01L51/46
CPCC07D495/10C07D519/00H10K85/636H10K85/6576H10K85/6572H10K85/657H10K30/00H10K50/15H10K50/00Y02E10/549
Inventor 刘坤坤苏仕健曹镛
Owner SOUTH CHINA INST OF COLLABORATIVE INNOVATION
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