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Regular polymer containing monofluorine-substituted benzo-hetero[1,3]diazole and preparation and application of regular polymer

A technology of benzoheteropolymers, applied in the field of organic photoelectric materials, to achieve the effect of good crystal arrangement, easy purification and simple synthesis route

Active Publication Date: 2016-06-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no research based on the regular and consistent arrangement of monofluorinated benzohetero[1,3]oxadiazole units along the main chain direction.

Method used

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  • Regular polymer containing monofluorine-substituted benzo-hetero[1,3]diazole and preparation and application of regular polymer
  • Regular polymer containing monofluorine-substituted benzo-hetero[1,3]diazole and preparation and application of regular polymer
  • Regular polymer containing monofluorine-substituted benzo-hetero[1,3]diazole and preparation and application of regular polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The chemical process formula in Example 1 is shown in the following formula, and the specific reaction steps and reaction conditions are as follows:

[0052]

[0053] (1) Compound 1 (4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole) is disclosed in the literature [Adv.Mater.2012,24,3646-3649] Prepared by the method, the specific steps are: dissolving 4-fluorobenzene-1,2-diamine in a mixed solvent of dichloromethane and triethylamine, adding thionyl chloride solvent dropwise with stirring in an ice water bath, and the crude product Purify with silica gel column to obtain 5-fluorobenzo[c][1,2,5]thiadiazole. Dissolve 5-fluorobenzo[c][1,2,5]thiadiazole in an aqueous hydrobromic acid solution, add liquid bromine dropwise with stirring at room temperature, and then heat to reflux overnight. The crude product is purified by silica gel column to obtain compound 1 (4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole).

[0054] (2) 4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole (comp...

Embodiment 2

[0077] The chemical process formula in Example 2 is shown in the following formula, and the specific reaction steps and reaction conditions are as follows:

[0078]

[0079] (1) Compound 1 (6.24g, 20mmol), tributyl (thiophen-2-yl) tin (6.71g, 18mmol), toluene (50mL), DMF (10mL) and catalyst Pd (PPh 3 ) 4 (200mg) Under argon atmosphere, heating under reflux and stirring for 6 hours. After extraction with dichloromethane, the crude product was purified with a silica gel chromatography column, petroleum ether and dichloromethane were used as gradient elution mobile phases to obtain a yellow solid product (compound 8, yield 88.7%).

[0080] The NMR data of compound 8 are as follows: 1 HNMR(CDCl 3 ,600MHz)δ(ppm): 8.08(dd,J=3.7,1.1Hz,1H), 7.67(d,J=10.0Hz,1H), 7.51(dd,J=5.0,1.1Hz,1H), 7.19( dd,J=5.0,3.8Hz,1H).

[0081] (2) Compound 8 (1.78g, 5.0mmol), tributyl(4-(2-decyltetradecyl)thiophen-2-yl)tin (10.65g, 15.0mmol), catalyst Pd(PPh 3 ) 4 (100mg), toluene (50mL) and DMF (10mL) under argon...

Embodiment 3

[0092] The chemical process formula in Example 3 is shown in the following formula, and the specific reaction steps and reaction conditions are as follows:

[0093]

[0094] (1) Compound 1 (4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole) is disclosed in the literature (Adv.Mater.2012,24,3646-3649) The method is prepared. The specific steps are to dissolve commercially available 4-fluorobenzene-1,2-diamine in a mixed solvent of dichloromethane and triethylamine, and add thionyl chloride solvent dropwise with stirring in an ice water bath. The crude product was purified with silica gel column to obtain 5-fluorobenzo[c][1,2,5]thiadiazole. Dissolve 5-fluorobenzo[c][1,2,5]thiadiazole in an aqueous hydrobromic acid solution, add liquid bromine dropwise with stirring at room temperature, and then heat to reflux overnight. The crude product is purified by silica gel column to obtain compound 1 [4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole].

[0095] (2) 4,7-Dibromo-5-fluorobenzene[...

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Abstract

The invention belongs to the field of organic photoelectric materials, and discloses a regular polymer containing monofluorine-substituted benzo-hetero[1,3]diazole, a preparation method of the regular polymer and application of the regular polymer in the field of organic photoelectric technologies. The structural formula of the polymer is shown as the first formula (please see the formula in the description), wherein x, y and z are separately independent and represent integers ranging from 0 to 5, n represents a positive integer ranging from 3 to 100,000, X1, X2 and X3 are separately independent and are selected from O or S or Se or Te or N-R or R-C-R or R-Si-R or R-Ge-R or R-Sn-R, R represents straight chains or branch chains or circular alkyl chains of C1-C30, R1, R2, R3 and R4 are separately independent and are selected from hydrogen, an alkyl group with 1-30 carbon atoms and an alkoxy group with 1-30 carbon atoms, an alkenyl group, an aryl group, a carboxyl group, a carbonyl group, an amino group, a cyano group, a nitryl group, an ester group, halogen and a halogenated alkyl group, and Ar is selected from a non-substituted or substituted electron-deficient conjugate unit group, an electron-rich conjugate group and a conjugate unit group formed by the units. The polymer can be applied to organic solar cell devices.

Description

Technical field [0001] The invention belongs to the field of organic optoelectronic materials, and in particular relates to a structured polymer containing monofluorine-substituted benzohetero[1,3]diazole and a preparation method thereof and its application in the field of organic optoelectronic technology. Background technique [0002] Organic optoelectronic materials have many advantages, such as light weight, easy processing, low cost, and the ability to make large-area flexible devices, due to their unique photophysical properties, and have received extensive attention in the past decade. [0003] In terms of organic solar cells, a research group in Nature Communication this year has reported that the energy conversion efficiency of single-layer polymer batteries has exceeded 10% (DOI: 10.1038 / ncomms6293), which indicates that organic solar cells have broad commercial prospects. However, compared with inorganic solar cells, the energy conversion efficiency of organic solar cell...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/123C08G61/126C08G2261/91C08G2261/3223C08G2261/212C08G2261/3246H10K85/649Y02E10/549
Inventor 黄飞周城张桂传曹镛
Owner SOUTH CHINA UNIV OF TECH
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