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Organic-functionalized non-aggregated phthalocyanine and preparation method thereof

A functional, non-aggregated technology, applied in the field of material science, can solve the problems of high raw material cost, high cost, unfavorable commercial application, etc., and achieve the effect of broad absorption spectrum

Inactive Publication Date: 2012-02-15
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor solubility of typical metal phthalocyanine materials, when preparing devices, the active layer can only be obtained by evaporation. Compared with the solution processing method, the process method is complicated, the conditions are harsh, and the cost is high, which is not conducive to practical application.
Although researchers have synthesized some metal phthalocyanine compounds with wide absorption and good solubility, its wide application is still limited due to the easy aggregation of phthalocyanine; although axial substitution can well inhibit the accumulation of phthalocyanine, the synthetic It is difficult, the cost of raw materials is high, it is not conducive to commercial application, and the absorption spectrum does not cover the entire visible light region. Therefore, a method for preparing a class of small molecule solar cell materials based on phthalocyanine with a broad absorption spectrum, no accumulation, and solution processability is very necessary

Method used

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  • Organic-functionalized non-aggregated phthalocyanine and preparation method thereof
  • Organic-functionalized non-aggregated phthalocyanine and preparation method thereof
  • Organic-functionalized non-aggregated phthalocyanine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: Preparation of Substituent A

[0054] Add p-cresol (2.156g, 20mmol) and 25mL of distilled water in a 100mL three-necked flask, and slowly add liquid bromine (2.256mL, 44mmol) dropwise under an ice bath. Stir at room temperature for 1 h, filter with suction, wash with water, dry, and perform column chromatography with petroleum ether as eluent to obtain 4.997 g of white solid product 2,6-dibromo-4-methylphenol, with a yield of 95%. NMR characterization data: 1 HNMR (500MHz, CDCl 3 ) δ (ppm): 7.26 (s, 2H), 5.70 (s, 1H), 2.26 (s, 3H).

[0055] Slowly add n-butyllithium (13.2mL) dropwise to 10mL fresh tetrahydrofuran (THF) dissolved with 3-octylthiophene (5.88g, 30mmol) at low temperature, lithiate for 2h, then add tributyltin chloride (10.74 g, 30mmol), reacted for 0.5h, warmed up to room temperature, reacted overnight, extracted with dichloromethane, and rotary evaporated to give a light yellow liquid tin compound of 3-octylthiophene, which was used direc...

Embodiment 2

[0057] Embodiment 2: Preparation of Substituent B

[0058] The p-cresol in Example 1 was replaced by p-Hydroxybenzaldehyde, and the feed ratio, reaction conditions and treatment methods were the same as in Example 1 to obtain substituent B with a yield of 69%. NMR characterization data: 1 H NMR (500MHz, CDCl 3 )δ(ppm): 10.01(s, 1H), 7.92(s, 2H), 6.92-6.80(s, 4H), 5.70(s, 1H), 2.69(t, 4H), 1.64-1.62(m, 4H ), 1.36-1.25 (m, 20H), 0.88 (t, 6H).

[0059] Preparation of substituent C

[0060] Phenol was used instead of p-cresol in Example 1, and the reaction conditions and treatment methods were the same as in Example 1 to obtain substituent B with a yield of 79%. NMR characterization data: 1 H NMR (500MHz, CDCl 3 )δ (ppm): 7.52 (s, 2H), 6.92-6.80 (s, 6H), 5.70 (s, 1H), 2.69 (t, 6H), 1.64-1.62 (m, 6H), 1.36-1.25 (m , 30H), 0.88(t, 9H).

Embodiment 3

[0061] Embodiment 3: Preparation of substituent D

[0062]Dissolve p-tolualdehyde (1.22 g, 10 mmol) and 4-nitrophenylacetonitrile (1.62 g, 10 mmol) in refined absolute ethanol (30 mL), dissolve 2.4 g of NaOH in 20 mL of absolute ethanol, and dropwise Added to the above solution, stirred at room temperature for 1 h, distilled under reduced pressure, cooled to obtain a dark green solid, filtered, rinsed with a large amount of water and dried to obtain substituent D with a yield of 60%. NMR characterization data: 1 H NMR (500MHz, DMSO) δ (ppm): 8.39(d, 2H), 8.08(s, 2H), 7.88(d, 2H), 7.41(d, 2H), 7.41(d, 2H), 6.82(d , 2H), 5.81 (s, 1H).

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Abstract

The invention belongs to a preparation method of a wide absorption organic solar energy cell material based on phthalocyanine. The solar energy cell material prepared by the invention is a micromolecular compound, which contains metal phthalocyanine rings, is connected with peripheral photolytic active groups, has large steric hindrance and can inhibit phthalocyanine accumulation on a certain degree. Different blocks in a molecule correspond to different absorptions, so as to realize phthalocyanine wide absorption; steric hindrance of the phthalocyanine peripheral substituent groups are utilized to inhibit aggregation of phthalocyanine rings, so as to obtain phthalocyanine based dissoluble micromolecular solar energy cell material with a wide absorption spectrum and no accumulation. A yield of the organic-functionalized non-aggregated phthalocyanine is higher than 51%; and various materials have wide UV visible absorption and are easily dissoluble in ordinary organic solvent; HOMO and LUMO energy levels of the synthesized phthalocyanine are coupled with that of common electron acceptors (PC61BM / PC71BM), so as to improve and enhance performances of a phthalocyanine based photovoltaic device.

Description

technical field [0001] The invention belongs to the field of material science, and in particular relates to the preparation of a phthalocyanine-based small molecule organic solar cell material. Background technique [0002] The phthalocyanine ring can be complexed with more than 70 elements, and the hydrogen atoms on the four benzene rings around the phthalocyanine can be replaced by various atoms or groups. These characteristics make phthalocyanine compounds have (1) excellent thermal and chemical stability (2) long exciton diffusion length (Lex) (3) unique absorption band, a visible light region (called Q Band), another near-ultraviolet region (called B band) at about 300-400nm (4) high hole mobility and other characteristics. Its applications have been extended from the original pigments and dyes to electroluminescent devices, sensitive devices in chemical sensors, organic solar cell materials, organic photoconductors, nonlinear optical materials, photosensitizers in pho...

Claims

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Application Information

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IPC IPC(8): C07D487/22H01L51/42
CPCY02E10/549
Inventor 王坤梁福顺付强
Owner NORTHEAST NORMAL UNIVERSITY
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