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Nine-membered fused ring derivatives as well as synthesis method and application thereof

A derivative and condensed ring technology, applied in the field of organic optoelectronics, can solve problems such as increasing device stability, and achieve the effects of low cost, increased conjugation, and high mobility

Active Publication Date: 2015-11-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, reports on OFET materials with higher mobility are relatively rare since then, and reports on threshold voltage and stability of OFET materials are even rarer, so there is still a lot to be done in terms of improving mobility, reducing threshold voltage, and increasing device stability. room for exploration

Method used

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  • Nine-membered fused ring derivatives as well as synthesis method and application thereof
  • Nine-membered fused ring derivatives as well as synthesis method and application thereof
  • Nine-membered fused ring derivatives as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0035] Synthesis of embodiment 13,9-dibromo-5,11-dihexadecyl indolecarbazole (1)

[0036]

[0037] Dissolve 3,9-dibromoindolecarbazole (1.0g, 2.4mmol) in a 250mL three-neck flask filled with 40mL dimethyl sulfoxide, and simultaneously add 50% potassium hydroxide solution (1.4mL) and tetrabutylammonium bromide (77mg, 0.24mmol), stirred under nitrogen atmosphere for 30min, then added hexadecyl bromide (2.2g, 7.2mmol). The reaction was warmed to 65°C and reacted for 4h. The reaction was then cooled to room temperature and poured into 300 mL of methanol with stirring. After suction filtration and washing with N,N-dimethylformamide, methanol and acetone for 1-3 times, 1.5 g of a light yellow powdery solid was finally obtained, with a yield of 72%.

Embodiment 23

[0038] Example 23, 9-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-dihexadecylindolecarbazole (2) Synthesis

[0039]

[0040] 3,9-dibromo-5,11-dihexadecyl indolecarbazole (1.0g, 1.1mmol), potassium acetate (1.08g, 11mmol) and bispinacol borate (0.9g, 3.5 mmol) was dissolved in a 100 mL three-necked round-bottomed flask filled with 50 mL of dioxane and stirred in a nitrogen atmosphere. When the temperature rose to 80°C, 1,1'-bisdiphenylphosphinoferrocenepalladium dichloride (40mg, 0.055mmol) was added rapidly. After 24 hours of reaction, it was cooled to room temperature and filtered with suction. The initial product of the filtrate was chromatographed on a silica gel / dichloromethane column to obtain 0.7 g of yellow needle-like crystals, with a yield of 63%.

Embodiment 33

[0041] Example 33, Synthesis of 9-bis(2-methylsulfinylphenyl)-5,11-dihexadecyl indolecarbazole (3)

[0042]

[0043] 10 mL of 2M K 2 CO 3Solution, 3,9-Bis(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-Dihexadecylindolecarbazole (2.0g, 2.1mmol) and 2-bromo(methylsulfinyl)benzene (1.42g, 6.5mmol) were dissolved in 100mL of toluene solution, while adding tetrakis(triphenylphosphine)palladium (100mg) and tetrabutylbromide Ammonium chloride (60mg), the reaction was heated to reflux for 24h. The reaction was then cooled to room temperature and extracted with dichloromethane. The organic phase was dried, distilled under reduced pressure and subjected to column chromatography using silica gel, ethyl acetate / petroleum ether (volume ratio 1:2) as the mobile phase to obtain a yellow viscous oily liquid (1.25 g, 61%).

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Abstract

The invention relates to nine-membered fused ring derivatives as well as a synthesis method and application thereof. According to the synthesis method, five-membered ring units are coupled with phenyl sulfoxide units for ring-fused reactions, so that aromatic compounds adopting the nine-membered macrocyclic structures are obtained. The nine-membered fused ring derivatives are high in thermal stability and hole mobility, and can serve as active layers applied to organic field-effect transistors, so that the organic field-effect transistors with high performance and stability are obtained.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and specifically relates to a class of nine-membered condensed ring derivatives and a synthesis method and application thereof. Background technique [0002] The earliest reports of organic field effect transistors can be traced back to the 1980s. In 1986, Ando et al. synthesized a p-type semiconductor material based on polythiophene units electrochemically, but at that time, the hole mobility of the material was only 10. -5 cm 2 V -1 the s -1 , the current switch ratio is only 100 (Appl. Phys. Lett., 1986, 49 (18), 1210-1212). Later, the emergence of small pentacene molecules made a great leap forward in the development of OFET materials. In 1997, Jackson et al. prepared small-molecule pentacene OFET devices with a regular stacking structure, and obtained a 1.5cm 2 V -1 the s -1 The hole mobility and 10 8 The switch current ratio (IEEE Electr. Device L., 1997, 18 (12), 606-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22C07D495/04C07F7/08H01L51/05
CPCC07D495/04C07D495/22C07F7/0816C07F7/0827H10K85/6576H10K85/657H10K10/46C07F7/08
Inventor 张斌杨勇杨伟曹镛
Owner SOUTH CHINA UNIV OF TECH
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