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Poly-squaric acid conjugated polymer preparation method and application thereof

A technology of conjugated polymers and polysquaric acid, which is applied in the preparation of polysquaric acid conjugated polymers, in the field of polysquaric acid conjugated polymers, can solve the problems of limiting the application of polysquaric acid materials, and achieve good Solubility, broad absorption spectrum, improved capture effect

Inactive Publication Date: 2012-03-21
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The solubility problem has greatly limited the application of polysquaric acid materials in the field of optoelectronic functional materials

Method used

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  • Poly-squaric acid conjugated polymer preparation method and application thereof
  • Poly-squaric acid conjugated polymer preparation method and application thereof
  • Poly-squaric acid conjugated polymer preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Polymer PVTVPS-Ph 2 preparation of

[0040] (1) Preparation of 3-dodecylthiophene

[0041]

[0042] Metal magnesium (3g, 123.46mmol) was added to a 250mL three-necked flask filled with 30mL of anhydrous ether, and then n-dodecyl bromide (24.92g, 100mmol) was added. Under argon protection, heat and reflux until the reaction of metal magnesium is complete, then add 20mg Ni(dppp)Cl 2 and 3-bromothiophene (16.3g, 100mmol), the mixture was heated to reflux for 12h and then poured into 200mL of ice-cold 2mol / L hydrochloric acid aqueous solution, the organic layer was separated, and the aqueous layer was extracted with ether (30mL×3), the organic phases were combined, and washed with over magnesium sulphate and dried overnight. After filtering off the desiccant, the solvent was distilled off, and then distilled under reduced pressure to obtain 18.40 g of a colorless oily substance of 3-dodecylthiophene, with a yield of 93%. Boiling point: 132°C-135°C / 800Pa [lite...

Embodiment 2

[0058] Embodiment 2: the preparation of PTPVPS-Ph

[0059] (1) Preparation of 4-dodecyloxyphenylboronic acid

[0060] Under the protection of argon, 4-dodecyloxybromobenzene (8.53g, 25mmol) and 80mL of anhydrous tetrahydrofuran were added to a 250mL three-necked flask, cooled to -35°C with liquid nitrogen-acetone, Slowly add 19 mL of n-butyllithium (1.6 mol / L, 30.4 mmol) dropwise, and keep at -35°C for 2 h after the dropwise addition. Cool to -78°C and keep for 2h; start to add 8mL of trimethyl borate dropwise, and keep at -78°C for 20min after the dropwise addition. Rise naturally to room temperature for 24 hours, add 40 mL of 20% hydrochloric acid, stir at room temperature for 1 hour, pour the reaction solution into 100 mL of water, extract with ether, wash with distilled water, and dry overnight over anhydrous magnesium sulfate. The desiccant was filtered off and the solvent was evaporated to obtain a white solid, which was then added to 10% dilute hydrochloric acid solut...

Embodiment 3

[0070] Example 3: PTPVS-C 12 preparation of

[0071] Polymer PVTVPS-C 12 The structure is as III, and its synthetic method is referred to (1)~(6) of example 1, and the difference with example 1 is that the reaction monomer adopted in the (4) step of example 1 is 4-bromomethyl-4'- dodecyloxybiphenyl, and this example uses 4-bromomethyl-4'-dodecyloxystyrylbenzene, and the subsequent steps are changed accordingly.

[0072] The product was a dark green solid in 88% yield. 1 H NMR (CDCl 3 , 400MHz, δ-ppm): 7.40 (br, 10H); 7.17 (br, 4H); 7.04 (br, 2H); 6.99-6.87 (br, 11H); 6.90 (br, 2H); 3.92 (br, 4H ); 1.77 (br, 4H); 1.42 (br, 4H); 1.26 (br, 54H); 0.87 (s, 9H). 13 C NMR (CDCl 3 , 100MHz, δ-ppm): 158.71, 139.98, 138.21, 135.96, 132.74, 127.96, 126.98, 125.05, 114.75, 68.07, 50.16, 31.93, 30.83, 29.65, 29.44, 29.31, 28.595, 26.09 13.61.

[0073]

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Abstract

The invention relates to a squaric acid polymer, and particularly relates to a poly-squaric acid conjugated polymer; the polymer has good dissolving stability, good matching between an absorption spectrum and a solar spectrum, and is applicable to polymer polymer solar cells. The invention also relates to a preparation method of the poly-squaric acid conjugated polymer and an application of the polymer. The technical solution schemes of the invention are that: 1) a large aromatic side chain, such as alkoxyphenyl, alkoxyphenyl methylene, alkoxybiphenyl methylene, and the like, is introduced onnitrogen atoms of pyrrole so as to reduce the accumulation between polymer molecular chains, to increase the dissolving stability of the polymer, and to improve the processing performance; 2) mesogenic fragments are introduced on nitrogen atoms of pyrrole so as to increase the local orderliness of the polymer.

Description

1. Technical field [0001] The invention relates to squarylium polymers, in particular to a class of squarylium conjugated polymers. The invention also relates to the preparation method of the polysquaric acid conjugated polymer and the application of the polymer. 2. Background technology [0002] Today, as energy issues become increasingly prominent, how to manufacture low-cost, high-efficiency solar cells has become the starting point of many scientific researches. Polymer solar cells (PSCs) are due to the diversity of organic systems, low raw material costs, low production costs, The advantages of low energy consumption and compatibility with flexible substrates have attracted many researchers. Through the efforts of researchers, in just ten years, its photoelectric conversion efficiency has increased from 10 -2 -10 -3 % increased to 7.73% [H.Chen, J.Hou, S.Zhang, et al.Nat.Photo., 2009, 3: 649], but there is still a lot of work to be done to meet the practical needs, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549Y02P70/50
Inventor 黄艳杨道宾霍二福蒋菁卢志云
Owner SICHUAN UNIV
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