Process for synthesizing 9,9-bisubstituted-2,7-dibromo fluorene or 9,9-bisubstituted fluorene

A technology of dibromofluorene and a synthesis method, which is applied in 9, can solve the problems of low yield, reduced quantum efficiency of luminescent materials, potential safety hazards of raw materials, etc., and achieves the effects of high yield, reduced molecular defects, and little environmental pollution.

Inactive Publication Date: 2006-05-24
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Their common ground is: operation has potential safety hazard of raw material aspect, as n-BuLi commonly used, is the raw material that is easier to burn, productive rate is low (ranging from 50% to 95%), It is easy to produce mono-substituted products, which are the defective parts in the macromolecular structure formed by the polymerization reaction
Gong et al. (Adv.Funct.Mater.2003, 13, 325) showed that under the catalysis of other metal ions, this polymer can easily lead to light or thermal catalytic oxidation reaction, forming a carbonyl group at the 9-position of fluorene The structure; and this carbonyl structure is a typical fluorescence extraction agent, resulting in a significant reduction in the quantum efficiency of electroluminescent materials

Method used

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  • Process for synthesizing 9,9-bisubstituted-2,7-dibromo fluorene or 9,9-bisubstituted fluorene
  • Process for synthesizing 9,9-bisubstituted-2,7-dibromo fluorene or 9,9-bisubstituted fluorene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1 9, the preparation of 9-diethylfluorene

[0029] Under anhydrous, anaerobic and nitrogen protection conditions, ethyl iodide (32ml, 0.40 parts) was dissolved in THF (80ml) to form a homogeneous solution, and then added dropwise to sodium tert-butoxide (48g , 0.50 parts) and fluorene (16.6 g, 0.10 parts) in THF (120 ml) solution. The color of the reaction system changes from blood red-black red-gray white, and the whole process lasts about 2.5 hours.

[0030] After the reaction is completed, the steps of extraction, drying, rotary evaporation, and oil pump to remove the residual solvent are used to obtain a light yellow oily crude product. The crude product was separated and collected by a silica gel column, and finally 21.7 g of a colorless oily liquid 9,9-diethylfluorene was obtained, with a yield of 97.6%.

Embodiment 2

[0031] Embodiment 2 9, the preparation of 9-diethylfluorene

[0032] Under anhydrous, oxygen-free, nitrogen protection conditions, bromoethane (37ml, 0.50 parts) and fluorene (16.6g, 0.10 parts) were dissolved in THF (120ml) to form a homogeneous solution, and then, at a speed of 4ml / min, Add dropwise to a solution of potassium tert-butoxide (67 g, 0.60 parts) in THF (60 ml). The color of the reaction system changes from blood red-black red-gray white, and the whole process lasts about 2.5 hours.

[0033] After the reaction is completed, the steps of extraction, drying, rotary evaporation, and oil pump to remove the residual solvent are used to obtain a light yellow oily crude product. The crude product was separated and collected by a silica gel column, and finally 21.8 g of a colorless oily liquid 9,9-diethylfluorene was obtained, with a yield of 98%.

Embodiment 3

[0034] Example 3 Preparation of 9,9-dibutyl-2,7-dibromofluorene

[0035] Under anhydrous, anaerobic, nitrogen protection conditions, n-bromobutane (27ml, 0.25 parts) was dissolved in THF (100ml) to form a homogeneous solution, then, with a speed of 4ml / min, was added dropwise to sodium tert-butoxide ( 38.5g, 0.40 parts) and 2,7-dibromofluorene (32.4g, 0.10 parts) in THF (150ml) solution. The color of the reaction system changes from blood red-black red-gray white, and the whole process lasts for about 2.5 hours.

[0036] After the reaction is completed, the steps of extraction, drying, rotary evaporation, and oil pump to remove the residual solvent are used to obtain a light yellow oily crude product. The crude product was separated and collected by a silica gel column, and finally 42.2 g of white solid 9,9-dibutyl-2,7-dibromofluorene was obtained with a yield of 97%.

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Abstract

The invention discloses a synthesis method of 9,9-disubstituent-2,7-dibromofluorene or 9,9-disubstituted fluorene. Under the conditions of anhydrous, oxygen-free and nitrogen protection, tetrahydrofuran of halogenated alkyl compound Solution, add metal alkoxide compound and 2,7-dibromofluorene (or fluorene) in tetrahydrofuran solution to react; or haloalkyl compound and 2,7-dibromofluorene (or fluorene) tetrahydrofuran solution, It can be added to the tetrahydrofuran solution of metal alkoxides for reaction. The synthesis method of the invention has the characteristics of high yield, short reaction time, safety, little environmental pollution and the like.

Description

technical field [0001] The invention relates to a synthesis method of 9,9-disubstituent-2,7-dibromofluorene or 9,9-disubstituent fluorene. Background technique [0002] In recent decades, due to the rapid development of organic light-emitting materials, especially the basic and applied research of organic electroluminescent materials, materials synthesized with fluorene and its derivatives as monomers have been widely used. Therefore, the simple, efficient, safe and economical preparation of the basic raw material 9,9-disubstituted-2,7-dibromofluorene or 9,9-disubstituted fluorene has considerable economic value. [0003] The synthesis of 9,9-disubstituted-2,7-dibromofluorene or 9,9-disubstituted fluorene has been reported in published literature. Two routes are mainly adopted: Route 1, the corresponding substituent group is attached to the 9-position of 2,7-dibromofluorene. U.S. Patent 6,512,083, B1 and World Patent WO 97 / 05184, and Xia et al. (Macromolecules, 2001, 34, 5...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C25/22C07C17/269C07C13/573C07C2/56
Inventor 薄志山黎静付亚琴
Owner INST OF CHEM CHINESE ACAD OF SCI
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