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Soluble functional carbazole derivant, preparation method and application thereof

A carbazole derivative, soluble technology, applied in the field of soluble functional carbazole derivatives, to achieve good thermal stability, high film shape stability, and simple synthesis

Inactive Publication Date: 2008-12-10
GUANG ZHOU NEW VISION OPTO ELECTRONICS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The molecular material has the advantages of good thermal stability, film stability and easy preparation.

Method used

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  • Soluble functional carbazole derivant, preparation method and application thereof
  • Soluble functional carbazole derivant, preparation method and application thereof
  • Soluble functional carbazole derivant, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1, 2-(p-(2-ethylhexyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane

[0033]

[0034] p-(2-Ethylhexyloxy)bromobenzene (5.68g, 20mmol) was dissolved in 80mL of dry tetrahydrofuran, protected, and cooled to -78°C with liquid nitrogen / isopropanol. 2.5M n-BuLi (10 mL, 25 mmol) was slowly added dropwise into the reaction flask, and the mixture changed from colorless to yellow. After the dropwise addition, continue to stir at -78°C for 1h, then add 4,4,5,5-tetramethyl-1,3,2-isopropanol borate (4.65g, 25mmol) with a syringe, yellow Disappeared immediately, then naturally warmed to room temperature and stirred for 24h. The mixture was washed with distilled water and CH 2 Cl 2 Extracted 3 times, the organic phase was extracted with MgSO 4 Let dry overnight. After the solvent was distilled off under reduced pressure, petroleum ether / CH 2 Cl2 Column chromatography gave a colorless oily liquid.

Embodiment 2

[0035] Embodiment 2,3, the preparation of 6-two pairs of (2-ethylhexyloxy) phenylcarbazoles:

[0036]

[0037] 2-(p-(2-ethylhexyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborinane (6.6g, 10mmol), 3, Add 6-dibromocarbazole (1.35g, 4.17mmol), toluene (40mL), ethanol (20mL), and 2M aqueous sodium carbonate solution (20mL) into a two-necked flask, and blow nitrogen gas to exhaust it for 30min. Catalytic amount of Pd(PPh 3 ) 4 (0.1g, 0.09mmol) was quickly added to the reaction flask, and then heated to 80°C for reflux for 12h. After the mixture was cooled, it was washed with distilled water and then washed with CH 2 Cl 2 Extracted 3 times, the organic phase was extracted with MgSO 4 dry. Column chromatography followed by recrystallization gave a white solid.

Embodiment 3

[0038] Embodiment 3,3, the preparation of 6-two p-tert-butylphenylcarbazole:

[0039]

[0040] 2-p-tert-butylphenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborinane (0.65 g, 2.5 mmol), 3,6-dibromocarbazole ( 0.325g, 1mmol), toluene (20mL), ethanol (10mL), and 2M sodium carbonate aqueous solution (10mL) were added into a two-neck flask, and nitrogen gas was bubbled to exhaust for 30min. Catalytic amount of Pd(PPh 3 ) 4 (46mg, 0.03mmol) was quickly added to the reaction flask, and then heated to 80°C for reflux for 12h. After the mixture was cooled, it was washed with distilled water and then washed with CH 2 Cl 2 Extracted 3 times, the organic phase was extracted with MgSO 4 dry. Column chromatography followed by recrystallization gave a white solid.

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Abstract

The invention discloses a carbazole derivative with soluble function, a preparation method and an application thereof. In the carbazole derivative with the soluble function, 4, 4'-N, N'-dicarbazole-diphenyl is taken as a center, wherein, the third position and the sixth position of one carbazole are introduced with alkyl, alkoxy, or phenyl substituted by fluorine atoms respectively, while the third position and the sixth position of the other carbazole are introduced with a rigid group Ar respectively. When the carbazole derivative with the soluble function is prepared, 3, 6-dibromo-carbazole is used as a reaction raw material; soluble groups are introduced to the third position and the sixth position of each carbazole through a Suzuki coupling reaction catalyzed by palladium; then, carbazole bromide of the soluble group is introduced; and finally, rigid groups are introduced, thereby preparing a target product. The carbazole derivative with the soluble function has a better solubility in a non-polar solvent with a higher boiling point, can be purified by a solution conveniently, simultaneously has excellent thermal stability and film morphologic stability, has advantages in synthesis, purification, film preparation and other aspects, and has important application prospect in organic film electroluminescent display, illumination and laser.

Description

technical field [0001] The present invention relates to soluble functional carbazole derivatives. It specifically relates to a functional carbazole derivative substituted by a soluble group and a non-coplanar rigid group and a preparation method thereof. The invention also relates to the application of the soluble functional carbazole derivative in the preparation of organic light emitting, lighting and laser devices. Background technique [0002] In 1987, Tang and VanSlyke of Kodak Corporation of the United States prepared a small molecule organometallic complex octahydroxyquinoline aluminum (Alq 3 ) as a "sandwich" (anode / luminescent layer / cathode) thin-film electroluminescent device as a light-emitting layer, creating a fundamental and applied research on electroluminescence with extremely small molecules. During the past two decades, organic light-emitting diodes (OLEDs) have attracted considerable attention due to their potential applications in next-generation display...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06H01L51/50H01L51/54
Inventor 朱旭辉赵利黄菊李远曹镛
Owner GUANG ZHOU NEW VISION OPTO ELECTRONICS TECH