- Improvement of Photoelectrochemical Properties of Chloroaluminum Phthalocyanine Thin Films by Controlled Crystallization and Molecular Orientation
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An orientation-controlled thin film of AlPcCl was prepared by vacuum deposition on a (001) surface of a KCl substrate.In the epitaxially film on KCl AlPcCl molecules stack cofacially, staggering around the Al-Cl-Al bonds and holding the molecular planes parallel to the KCl surface.At a low substrate temperature the deposit was a uniform and closely oriented thin film.As the substrate temperture increased, the film became rugged and cracked due to growth of a large size of crystallites.The photovoltaic properties of the oriented AlPcCl film were measured in a photoelectrochemical cell of ITO/AlPcCl/I3-, I-/Pt.The oriented AlPcCl films showed good rectifying I-V curves of p-type conductance and cathodic photocurrents under illumination of white light.As compared to amorphous or polycrystalline AlPcCl films, photovoltaic efficiency was improved especially in increase of Isc by the epitaxial orientation.The photocurrent quantum yield of the uniform thin film with epitaxial orientation was 25 times as high as that of the rugged and cracked polycrystalline film with large crystallites.The epitaxial AlPcCl film showed an intense peak at 830 nm in the photocurrent action spectrum, which could be attributed to carrier generation from charge-transfer excitons of the cofacially stacked molecules.It was concluded that the reason for the improvement of the photovoltaic properties was that exciton diffusion and charge carrier mobility were larger through the molecular column in the epitaxial film, while exciton trapping and recombination of carriers were probably caused in grain boundaries between crystallites in the polycrystalline film.
- Yanagi, Hisao,Douko, Shinya,Ueda, Yasukiyo,Ashida, Michio,Woehrle, Dieter
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- Orientation and morphology of chloroaluminum phthalocyanine films grown by vapor deposition: Electrical field-induced molecular alignment
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The electric field influence on the molecular orientation and the surface morphology of the chloroaluminum(III) phthalocyanine (AlClPc) films has been studied using polarization dependent Raman spectroscopy and atomic force microscopy. The experimental studies were supported by DFT quantum chemical computations of the AlClPc vibrational spectra and 15N isotopic shifts. The electric field of 1.4 kV mm-1 applied parallel to the substrate plane during the physical vapour deposition modified the film structure noticeable. The AlClPc molecules were aligned nearly perpendicular to the substrate surface (the mean tilt angle increased to ~80° from ~20° in the films grown without the electric field). The AFM images of the AlClPc films grown in the absence of electric field revealed a predominant amount of crystallites of polyhedron shape, whereas in the case of the applied electric field the surface was more ordered and consisted of the crystallites of a smoother shape.
- Basova, Tamara V.,Kiselev, Vitaly G.,Plyashkevich, Vladimir A.,Cheblakov, Pavel B.,Latteyer, Florian,Peisert, Heiko,Chassè, Thomas
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- Highly photoactive molecular semiconductors: Determination of the essential parameters that lead to an improved photoactivity for modified chloroaluminum phthalocyanine thin films
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Thin films of chloroaluminum, chlorogallium, and chloroindium phthalocyanines (ClAlPc, ClGaPc, and ClInPc) have been sublimed on SnO2 substrates maintained during sublimation at temperatures ranging from -130 to 190°C. Using this procedure, it is possible to obtain molecular semiconductor layers with a structure varying from amorphous to polycrystalline. These layers were immersed in KI3/KI or KCl solutions at pH = 3.0. This treatment was found to improve drastically the photoelectrochemical activity of ClAlPc thin films. Short-circuit photocurrents Jsc = 0.75 ± 0.25 mA/cm2 were obtained, using polychromatic illumination (35 mW/ cm2), after immersion of ClAlPc into KCl solutions while lower Jsc values (0.3 ± 0.1 mA/cm2) were obtained for KI3/KI solutions. No change in the photoactivity was observed either for ClGaPc or for ClInPc when they were immersed in the same solutions. Both molecular semiconductors provided lower short-circuit photocurrents (Jsc ≤ 0.15 ± 0.03 mA/cm2 for ClGaPc; Jsc ≤ 0.20 ± 0.02 mA/cm2 for ClInPc). The characterization of the chloro-trivalent metal phthalocyanine films indicates that the hydrolysis of the metal-Cl bond is essential for the occurrence of the physicochemical transformation leading to improved photoactivity. The Al-Cl bond of ClAlPc hydrolyzes, but this reaction does not occur for ClGaPc or for ClInPc. In contact with KI3/KI or KCl solutions at pH = 3.0, bulk hydrolysis occurs for ClAlPc, only if both H3O+ and an anion could diffuse from the solution into the material. The large I3- anion is prevented from doing so for polycrystalline ClAlPc films obtained by sublimation on SnO2 substrates maintained at 180°C. However, it can diffuse easily in more disorganized films obtained at lower substrate temperatures. Powders of the chlorotrivalent metal phthalocyanines as well as bromoaluminum phthalocyanine (BrAlPc) were used to quantify anion incorporation in these materials. After complete hydrolysis of BrAlPc (powder) and ClAlPc (films) there are ca. 50-85% of the anions, generated in situ by the hydrolysis reaction or diffusing from the solution as a consequence of the hydrolysis reaction, that remain in the Pc material. Thus, ca. 50-85% of the protons released by the hydrolysis either protonate the macrocycles or react with Pc+O2- already present in the film. In both cases, anions are necessary to neutralize the excess of positive charges. H2O is also found in the modified films. The presence of protonated Pcs, of anions, and of H2O into what is now HOAlPc (after ClAlPc hydrolysis) modifies the structure of the material as well as its photoactivity.
- Santerre,Cote,Veilleux,Saint-Jacques,Dodelet
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- The influence of NO2 on the conductivity of chloro-aluminium phthalocyanine thin films
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The electrical behaviour of chloro-aluminium-phthalocyanine (ClA1Pc) thin films was studied in the presence of NO2 and O2 gases. The change in the dark conductivity of these ClA1Pc thin films on exposure to NO2 was measure
- Krier,Azim-Araghi
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- Phase behaviour of halogenated metal phthalocyanines
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The phase behaviour of chloro-aluminium phthalocyanine, chloro-indium phthalocyanine, bromo-indium phthalocyanine, dichloro-tin phthalocyanine, and dichloro-platinum phthalocyanine is studied using differential scanning calorimetry, X-ray diffraction, and
- Napier,Collins
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- Axially phenoxylated aluminum phthalocyanines and their application in organic photovoltaic cells
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Novel axially phenoxylated aluminium phthalocyanines, pentafluorophenoxy aluminium phthalocyanine (F5PhO-AlPc) and p-nitrophenoxy aluminium phthalocyanine (NO2PhO-AlPc), were synthesized through a one-step reaction starting from the commonly used photoactive material, chloro aluminium phthalocyanine (Cl-AlPc), and the respective phenols. Reactions with other phenols did not yield corresponding AlPc derivatives. Optical, electrical, and thermal analyses were carried out on F5PhO-AlPc and NO2PhO-AlPc using UV-Vis measurements (solution and thin-film), cyclic voltammetry (CV), differential-pulse voltammetry (DPV), and thermogravimetric analysis (TGA). A simple thermodynamic model was used to explain the lack of reaction when Cl-AlPc was treated a variety of alkylated phenols. We noted a side reaction producing fluoro aluminium phthalocyanine (F-AlPc) when the synthesis of F5PhO-AlPc was attempted in DMF. The model also explains this observation. F5PhO-AlPc and NO2PhO-AlPc were integrated into organic photovoltaic devices (OPVs) both as electron-donating and as electron-accepting materials. The phenoxy-AlPcs enable an enhancement of the open-circuit voltage (VOC) of the OPVs when applied as either an electron donor or as an electron acceptor compared to Cl-AlPc. The results within the OPV, specifically the increased VOC, are consistent with the steric shielding effect seen in other OPVs.
- Raboui, Hasan,Al-Amar, Mohammad,Abdelrahman, Ahmed I.,Bender, Timothy P.
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- A New Polymorph of Hydroaluminum Phthalocyanine. Characterization and Photoactivity
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Sublimed films of α-form hydroxyaluminum phthalocyanine (α-PcAlOH) can be transformed into a novel polymorph by a treatment with aqueous acid solutions.The spectroscopic characterization of the new polymorph, showing its particular visible and IR spectra and X-ray diffraction pattern was achieved by comparing with other polymorphs.The dimorphic transformation of PcAlOH is also associated with a dramatic enhancement in photoactivity as shown in the performance of a photoelectrochemical cell based upon a PcAlOH/redox junction.
- Dao, le H.,Perrier, Gerard
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- COMPOUND, PHOTOSENSITIVE RESIN COMPOSITION COMPRISING SAME, PHOTORESIST, COLOR FILTER AND DISPLAY DEVICE
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The present specification provides a compound represented by chemical formula 1 and a photosensitive resin composition including the same. A photosensitive material, a color filter and a display device are provided.
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Paragraph 0218-0221
(2021/01/01)
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- Phthalocyanine compound with high thermal stability and high chemical resistance, method for production thereof and ink composition and printing article using the same
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The present invention relates to an aluminum phthalocyanine compound substituted with an ethoxy group having excellent heat resistance and chemical resistance, a method for preparing the same, an ink composition and a printed article using the same. To the present invention, an ethoxy aluminum phthalocyanine compound having 1 a structure represented by the following formula, which is a phthalocyanine 650 - 840 nm-substituted phthalocyanine in which an ethoxy group 1050nm is substituted with aluminum in a central metal, is synthesized with high yield. The compound of formula ([I) as claimed in 1] Claim (by machine translation)
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Paragraph 0070-0076
(2020/02/10)
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- Phthalocyanine pigment
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PROBLEM TO BE SOLVED: To provide a phthalocyanine pigment having excellent fastness (heat resistance, light fastness and solvent resistance), excellent color characteristics (brightness) and a contrast ratio when used for a color filter or the like, and free of generation of foreign substances caused by association or aggregation of molecules even in a high temperature environment at over 230°C. SOLUTION: The phthalocyanine pigment is represented by formula (1). In the formula, X represents a halogen atom; n represents an integer of 4 to 16, where an average substitution number of X is 6 to 15 and a halogen distribution width is 4 or more; Y represents -OP(=O)R1R2, -OC(=O)R3, -OS(=O)2R4, or OH; and R1 to R4 represent H, OH, an alkyl group, an aryl group, an alkoxy group, an aryloxy group or the like, which may have a substituent. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0070; 0071
(2018/09/02)
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- A method of manufacturing the organic pigment (by machine translation)
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PROBLEM TO BE SOLVED: required high contrast and organic pigment particle dispersion stability. SOLUTION: good solvent and an organic pigment solution obtained by dissolving the organic pigment, and good compatibility with the organic pigment and the solvent and solvent to the Oligophagous comprising, respectively, a raw material supply flow path (A, B) is different from, and coupled to a raw material supply flow path in the outlet channel (C) 2 is formed by mixing the pigment particles, the fluid in the supply passage of the organic pigment particles 1000-10000 Reynolds number conditions by the organic pigment particles are precipitated. Aluminum phthalocyanine pigment org. pigment, which is a good solvent, N, N, -dimethyl formamide, N, N, - dimethyl acetamide , 1-methyl-2-pyrrolidone, dimethyl sulfoxide or production of organic pigment. Selected drawing: fig. 1 (by machine translation)
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Paragraph 0152
(2016/12/16)
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- The method for manufacturing the same and subphthalocyanine compd. (by machine translation)
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PROBLEM TO BE SOLVED: dispersion properties, good stability, strength, hue, brightness, contrast subphthalocyanine compd. coloristic characteristics and its manufacturing method. SOLUTION: phthalocyanine compounds obtained by the reaction of phosphorus compound of aluminum and eq. (3) subphthalocyanine compd. eq. (2). [ In the formula, R is OH or halogen atoms. X represents a direct bond or O. Y is OH or halogen atoms. However, R and Y is a halogen atom and not simultaneously. ] Selected drawing: fig. 1 (by machine translation)
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Paragraph 0032-0033
(2016/11/09)
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- PHTHALOCYANINE SYNTHESIS
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Provided are methods for preparing a phthalocyanine pigment in high yield that eliminate the need to add a heavy metal catalyst. The resulting pigmentary phthalocyanine products thus contain no or only trace amounts of heavy metal impurities. The provided methods produce phthalocyanine pigments that can be used in any application that utilizes phthalocyanine pigments, such as in dispersions, printing inks, paints, plastics and coatings.
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Paragraph 0143; 0144
(2014/07/08)
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- PHTHALOCYANINE SYNTHESIS
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Provided are methods for preparing a phthalocyanme pigment in high yield that eliminate the need to add a heavy metal catalyst. The resulting pigmentary phthalocyanme products thus contain no or only trace amounts of heavy metal impurities. The provided methods produce phthalocyanme pigments that can be used in any application that utilizes phthalocyanme pigments, such as in dispersions, printing inks, paints, plastics and coatings.
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Page/Page column 30-31
(2013/03/26)
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- m-OXO CROSSLINKED DISSIMILAR METAL PHTHALOCYANINE COMPOUND AND PROCESS FOR SELECTIVELY PRODUCING THE SAME
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An object of the present invention is to provide a novel μ-oxo bridged heterometal phthalocyanine compound, and a production method such that the μ-oxo bridged heterometal phthalocyanine compound is obtained simply, selectively and with high yield. The μ-oxo bridged heterometal phthalocyanine compound has a structure in which the central metal atom (M1) in a metal phthalocyanine including M1 as central metal thereof is oxo-bridged with the central metal M2 in a metal phthalocyanine including M2 as central metal thereof.
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Page/Page column 7
(2008/06/13)
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- Mu-oxo bridged heterometal compound and selective production method thereof
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An object of the present invention is to provide a new μ-oxo bridged heterometal compound, which can make the photo-functional materials to have diversified properties, and a production method such that the μ-oxo bridged heterometal compound is obtained simply, selectively and with high yield. The present invention provides μ-oxo bridged heterometal compounds, NcM1-O-M2Nc, PcM1-O-M2Nc and NcM1-O-M2Pc wherein Nc represents naphthalocyanine, Pc represents phthalocyanine, M1 represents a metal atom which is able to have a valence of up to three, and M2 represents a metal atom which is able to have a valence of four or five.
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