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Asymmetric fluoreno imidazole derivative and preparation method thereof

A technology of fluorenimidazole and derivatives, which is applied in the field of asymmetric fluorenimidazole derivatives and their preparation, to achieve the effects of enhancing blue light emission performance, overcoming poor chemical stability, and overcoming solubility reduction

Inactive Publication Date: 2015-04-29
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, there are still few studies on fluorene-based luminescent materials that selectively incorporate heterocycles at the 2, 3-position and introduce functional groups at the 7-position to improve their luminous efficiency and luminous chromaticity.

Method used

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  • Asymmetric fluoreno imidazole derivative and preparation method thereof
  • Asymmetric fluoreno imidazole derivative and preparation method thereof
  • Asymmetric fluoreno imidazole derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] Dissolve 1g of 2,3-diamino-7-halo-9,9′-dioctylfluorene and 1 times the molar amount of benzaldehyde in 20mL of dioxane, react at 90°C for about 10 hours, stop After the reaction, cooling to remove the solvent, separation and purification by column chromatography gave 0.94 g of light yellow solid (yield: 80%). 1HNMR (500M, CDCl 3 ): δ(ppm) 8.18-8.09(m, 2H),7.68(s, 1H),7.58-7.37(m, 7H),2.03-1.90(m, 4H),1.24-0.98(m, 20H),0.86 -0.56(m, 10H).

Embodiment 2

[0037]

[0038] Add 100 mg of bromofluorenimidazole compound, 1.2 times the molar amount of phenylboronic acid, 2 times the molar amount of potassium carbonate and 0.05 molar amount of bistriphenylphosphine palladium dichloride to toluene (8 mL) and water (1 mL) In a mixed solvent, under the protection of nitrogen, the reaction was carried out at 90°C for 12 hours, the reaction was stopped and cooled to room temperature, and the solvent was removed, followed by column chromatography separation and purification to obtain 90 mg of light yellow solid (yield: 90%). 1 HNMR (500M, CDCl 3 ): δ(ppm)8.17(d, J =8.0 Hz,2H),7.85(s, 1H),7.75-7.67(m, 3H),7.66-7.54(m, 3H),7.53-7.44(m, 5H),7.40-7.35(m, 1H), 2.07-1.97(m, 4H), 1.22-0.98(m, 20H), 0.84-0.67(m, 10H). HR-MS (ESI, m / z): [M+H] + calcd for (C 42 h 50 N 2 ) 583.4052; found, 583.4038.

[0039] The excitation spectrum and emission spectrum of the compound were measured by a fluorescence spectrophotometer, and the optimum excit...

Embodiment 3

[0041]

[0042] Add 100 mg of bromofluorenimidazole compound, 1.5 times the molar amount of naphthaleneboronic acid, 2 times the molar amount of potassium carbonate and 0.05 molar amount of bistriphenylphosphine palladium dichloride to toluene (12 mL) and water (1 mL) In a mixed solvent, under the protection of nitrogen, react at 90°C for 12 hours, stop the reaction and cool to room temperature. After removing the solvent, column chromatography separates and purifies 98 mg of yellow solid (yield: 91%). 1 HNMR (500M, CDCl 3 ): δ(ppm) 8.26(d, J =7.5 Hz, 2H),8.05-7.82(m, 4H),7.76(d, J =8.0 Hz, 1H), 7.63-7.41(m, 10H), 2.13-1.92(m, 4H), 1.22-1.03(m, 20H), 0.91-0.69(m, 10H). HR-MS (ESI, m / z): [M+H] + calcd for (C 46 h 52 N 2 ) 632.4208; found, 632.4220.

[0043] The excitation spectrum and emission spectrum of the compound were measured by a fluorescence spectrophotometer, and the optimum excitation wavelength was determined to be 359nm, and the maximum emission wavelengt...

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Abstract

The invention relates to an asymmetric fluoreno imidazole derivative and a preparation method thereof. A structural formula of the derivative is as shown in the specification, wherein R1 is H and C1-C20 linear or branched alkyl; R2 is H and C1-C20 linear or branched alkyl; or more than 10 substituent groups in the structural formula are C5-C7 cycloalkyl. The alkyl on the periphery of the molecule of the derivative provided by the invention is conducive to overcoming solubleness reduction caused by a high planar rigidity structure of the molecule and improving the dissolving processing performance of the material molecule. The blue-light luminescent performance of the molecule is strengthened by introduced imidazole ring; meanwhile, conjugating of phi electrons on the framework of the molecule is further strengthened, so that an energy gap of the molecule is reduced; the derivative can play a certain role in overcoming the defects of poor chemical stability and the like of traditional organic small molecular materials, and can be widely applied to the fields of organic semiconductor materials, nonlinear optical materials, biochemical sensors and solar cells.

Description

technical field [0001] The invention relates to an unsymmetrical fluorenimidazole derivative and a preparation method thereof. Background technique [0002] Since the 21st century, with the rapid development of the information industry, mankind has entered the era of knowledge economy. The transmission, processing, storage and display of information has become the development direction and goal of information science and technology. In 2000, after polyacetylene, an organic conductive material, won the Nobel Prize in Chemistry, organic electroluminescent materials developed rapidly, and new materials with superior performance, longer life, and easy-to-make devices continued to emerge. [0003] Organic electroluminescent devices have the advantages of low DC voltage drive that can match integrated circuits, active luminescence, small size of full color, no viewing angle limitation, bendable folding, wide operating temperature range, simple manufacturing process, and a wide ra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C09K11/06
CPCC07D235/02C09K11/06C09K2211/1007C09K2211/1011C09K2211/1044
Inventor 顾泽彬林海霞崔永梅郝增帅
Owner SHANGHAI UNIV
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