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Indoline [3,2-a] carbazole and pyridine derivatives and their preparation method, application and device

A technology of pyridine derivatives and indoline, which is applied in electric solid devices, semiconductor devices, chemical instruments and methods, etc., can solve the problems of insufficient hole mobility, low glass transition temperature, etc., and achieve good hole Transmission capacity, improved transmission capacity, effect of high glass transition temperature

Active Publication Date: 2020-09-04
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] These hole transport materials generally have a mobility of about 10 -4 ~10 -6 cm 2 / Vs, but there is a low glass transition temperature, insufficient hole mobility, the development of new high-mobility hole-transporting groups, good amorphous film-forming properties, and light stability, thereby improving the efficiency of the device

Method used

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  • Indoline [3,2-a] carbazole and pyridine derivatives and their preparation method, application and device
  • Indoline [3,2-a] carbazole and pyridine derivatives and their preparation method, application and device
  • Indoline [3,2-a] carbazole and pyridine derivatives and their preparation method, application and device

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Embodiment 1

[0065] S-1 provided by the present invention can be synthesized by the following method.

[0066] 1) 1H,1'H-2,3'-diindole and (dimethylamino)acetaldehyde dimethyl acetal are fed in a molar ratio of 1:1~3, added to acetic acid and stirred for 6 hours, rearranged to obtain an intermediate, The yield is 91%;

[0067] 2) Tetrakistriphenylphosphinepalladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) were added to isoquinoline-3-boronic acid (61g, 366mmol) and intermediate (45.9g, 183mmol) Tetrahydrofuran (500 mL), and the mixture was heated under reflux for 4 hours, the reaction mixture was cooled to room temperature, and then the solvent was removed by rotary evaporation. The final product was obtained by silica gel column chromatography. MS: 510.18, purity 98.2%.

Embodiment 2

[0069] S-2 provided by the present invention can be synthesized by the following method.

[0070] 1) 1H,1'H-2,3'-diindole and (dimethylamino)acetaldehyde dimethyl acetal are fed in a molar ratio of 1:1~3, added to acetic acid and stirred for 6 hours, rearranged to obtain an intermediate, The yield is 91%;

[0071] 2) Tetrakistriphenylphosphine palladium (2.1 g, 1.83 mmol) and potassium carbonate (75.7 g, 549 mmol) were added to benzo[G]isoquinoline-3-boronic acid (81.6 g, 366 mmol) and intermediate (45.9 g, 183 mmol) in degassed tetrahydrofuran (500 mL), and the mixture was heated at reflux for 4 hours, the reaction mixture was cooled to room temperature, and then the solvent was removed by rotary evaporation. The final product was obtained by silica gel column chromatography. MS: 610.22, purity 98.6%.

Embodiment 3

[0073] S-3 provided by the present invention can be synthesized by the following method.

[0074] 1) 1H,1'H-2,3'-diindole and (dimethylamino)acetaldehyde dimethyl acetal are fed in a molar ratio of 1:1~3, added to acetic acid and stirred for 6 hours, rearranged to obtain an intermediate, The yield is 91%;

[0075] 2) Tetrakistriphenylphosphine palladium (2.1 g, 1.83 mmol) and potassium carbonate (75.7 g, 549 mmol) were added to benzo[h]isoquinoline-3-boronic acid (81.6 g, 366 mmol) and intermediate (45.9 g, 183 mmol) in degassed tetrahydrofuran (500 mL), and the mixture was heated at reflux for 4 hours, the reaction mixture was cooled to room temperature, and then the solvent was removed by rotary evaporation. The final product was obtained by silica gel column chromatography. MS: 610.22, purity 97.3%.

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Abstract

The invention belongs to the technical field of photoelectric material application technology, and specifically relates to indoline [3,2-a] carbazole and pyridine derivatives and their preparation methods, applications and devices. The derivatives of indoline [3,2-a] carbazole and pyridines provided by the present invention use indoline [3,2-a] carbazole and pyridines as basic structural units, after modification get an asymmetric structure. The compound provided by the invention is a kind of compound with high glass transition temperature and electron transport ability of holes. When it is used as a hole-transporting material, it is compatible with hole-transporting groups such as 4,4', 4"-tris(carbazole-9-yl)triphenylamine (TCTA), a commonly used hole-transporting material in the prior art. Compared with traditional materials, the transport ability of holes and electrons has been significantly improved. In organic electroluminescent devices, compared with traditional hole transport materials, this series of compounds has better performance in terms of glass transition temperature, current efficiency, power efficiency, external quantum Efficiency and roll-off have been significantly improved, and it is an ideal hole transport material.

Description

technical field [0001] The invention belongs to the technical field of photoelectric material application technology, and specifically relates to a preparation method, application and device of indoline [3,2-a] carbazole and pyridine derivatives. Background technique [0002] Organic Light-emitting Diode (Organic Light-emitting Diode) is also known as organic electroluminescent device or organic light-emitting display (Organic Light-emitting Display, OLED), the principle is a kind of positive, A display device prepared by the phenomenon that the negative electrode enters the organic solid light-emitting layer to recombine and emit light (Tang, C.W. et al. Appl. Phys. Lett. 1987, 52, 913). Devices mainly use organic small molecule / polymer semiconductor materials. Due to the characteristics of easy preparation, processing, purification and highly selective modification of organic small molecules and polymer materials, they have great potential in the field of material applicat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/00H01L51/54H01L51/46
CPCY02E10/549
Inventor 穆广园刘飞鸽庄少卿
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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