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Soluble tetraalkyl phthalocyanine compound and preparation method thereof

A tetraalkyl phthalocyanine and soluble technology, which is applied in the field of soluble tetraalkyl phthalocyanine compounds and their preparation, can solve the problems of high cost, harsh conditions, complicated processing methods, etc., and achieves simple structure, mild reaction conditions and good dissolution. sexual effect

Inactive Publication Date: 2008-09-03
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

U.S. Patent 5,969,376 discloses a p-channel organic thin film transistor adopting planar metal phthalocyanines (copper phthalocyanine (CuPc), zinc phthalocyanine (ZnPc), tin phthalocyanine (SnPc)) as a semiconductor layer; Journal of the American Chemical Society ( J.Am.Chem.Soc., 1998,120,207-208) have reported the use of planar metallophthalocyanines (hexadecafluorometallophthalocyanines (F 16 MPc), iron hexadecyl chlorophthalocyanine (Cl 16 FePc), octacyano substituted copper phthalocyanine ((CN) 8 CuPc)) as an n-channel organic thin film transistor of the semiconductor layer; 2006 Appl. (Cl 16 CuPc)) n-channel organic thin film transistor; Chinese patent 02129458.5 discloses a p-channel organic thin film transistor using non-planar metal phthalocyanine (titanium phthalocyanine (TiOPc), vanadyl phthalocyanine (VOPc)); Chinese patent 200710055258.1 discloses an organic thin film transistor using an axially substituted phthalocyanine compound; advanced materials (Adv. The conversion efficiency reaches 5%, but the above-mentioned materials are prepared by the vacuum evaporation processing method to prepare the organic semiconductor layer. Compared with the solution processing method, the process method is complicated, the conditions are harsh, and the cost is high. The advantages of organic semiconductor materials, the preparation of solution-processable phthalocyanine compounds is an inevitable requirement for the development of materials and technologies

Method used

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  • Soluble tetraalkyl phthalocyanine compound and preparation method thereof
  • Soluble tetraalkyl phthalocyanine compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Example 1: 4-(1-Butynyl)phthalonitrile

[0029] Add 4-iodophthalonitrile (2.1g, 8.0mmol), CuI (0.61g, 3.2mmol) and Pd(PPh) to a 150ml ampoule 3 ) 4 (0.23g, 0.32mmol) The gas was replaced with high-purity nitrogen three times, and a mixed solvent of 80 ml of triethylamine and 20 ml of tetrahydrofuran was added to it. Freeze 1-butyne into a liquid in an ice-salt bath, use a syringe to extract 1-butyne (0.86g, 16mmol) into the above ampoule, seal the tube, stir at room temperature for 24 hours, stop the reaction, pour 400ml In ether, extract with enough ammonium chloride solution until the pH of the organic layer is 7, wash with saturated brine, dry with anhydrous magnesium sulfate, and rinse with a mixture of petroleum ether / ethyl acetate with a volume ratio of 10:1 The reagent was separated by column chromatography to obtain 1.2 g of 4-(1-butynyl)phthalonitrile with a yield of 85%. NMR characterization data: 1 H NMR(300MHz, CDCl 3 ) δ (ppm) 7.74 (d, 1H), 7.71 (d, 1H), 7.68 (...

Embodiment 2

[0030] Example 2: 4-(1-octynyl)phthalonitrile

[0031] 4-iodophthalonitrile (2.1g, 8.0mmol), CuI (0.61g, 3.2mmol) and Pd(PPh 3 ) 4 (0.23g, 0.32mmol) was added to a 150ml reaction flask, the gas was replaced with high-purity nitrogen three times, and a dried mixed solvent of 80ml triethylamine and 20ml tetrahydrofuran was added to the reaction flask. Finally, add n-octyne (1.5g, 10mmol), react at room temperature for 17 hours, stop the reaction, pour it into 500 ml of ether, extract with enough ammonium chloride solution until the organic layer pH is 7, and wash with saturated brine. Drying with water magnesium sulfate, using a mixture solvent of petroleum ether / ethyl acetate with a volume ratio of 10:1 as the eluent for column chromatography to obtain 1.8 g of 4-(1-octynyl)phthalonitrile. The rate is 97%. NMR characterization data: 1 H NMR(300MHz, CDCl 3 )δ(ppm) 7.75(d, 1H), 7.70(d, 1H), 7.66(dd, 1H), 2.44(t, 2H), 1.60(m, 2H), 1.42(m, 2H), 1.31(m , 4H), 0.90 (t, 3H).

Embodiment 3

[0032] Example 3: 4-(1-Dodecynyl)phthalonitrile

[0033] Using n-dodecyne hydrocarbon instead of n-octyne in Example 2, the feed ratio, reaction conditions and treatment methods were the same as those in Example 2, to obtain 4-(1-dodecynyl)phthalonitrile with a yield of 95%. NMR characterization data: 1 H NMR(300MHz, CDCl 3 )δ(ppm) 7.75(d, 1H), 7.69(d, 1H), 7.64(dd, 1H), 2.40(t, 2H), 1.62(m, 2H), 1.42(m, 2H), 1.30(m , 8H), 0.90 (t, 3H).

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Abstract

The invention relates to soluble tetra-alkyl phthalocyanine compounds and a method for making the same. The soluble tetra-alkyl phthalocyanine compounds have the following general structure, wherein Rn represents straight-chain or branching chain alkane, n represents the number of straight-chain or branching chain alkane, M represents center ligand of bivalence or more, L represents axial ligand, X represents the number of L. the soluble tetra-alkyl phthalocyanine compounds uses 4-alkyl phthalonitrile as starting material, have good solubility in organic solvent, have processing characterics in solution, and have potential applications in photoelectron material and information technology fields.

Description

Technical field [0001] The invention belongs to the field of optoelectronic materials and information technology, and relates to a soluble tetraalkyl phthalocyanine compound and a preparation method thereof. technical background [0002] As soon as the phthalocyanine compound came out, it attracted worldwide attention for its unique color, low production cost, excellent stability and colorability. So far, the phthalocyanine ring (Pc) can be complexed with 70 kinds of elements, and the four benzene rings around the phthalocyanine ring (Pc) can be replaced by many atoms or groups. These characteristics make the phthalocyanine compound has a rich chemical structure and physical properties. The application fields of phthalocyanine compounds have involved sensitive devices in chemical sensors, electroluminescence devices, photovoltaic materials, high mobility materials, optical disc information recording materials, electrophotographic materials, liquid crystal display materials, nonli...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07F19/00
Inventor 耿延候田洪坤董少强
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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