CN1438639A - Otical recording material - Google Patents
Otical recording material Download PDFInfo
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- CN1438639A CN1438639A CN03104386A CN03104386A CN1438639A CN 1438639 A CN1438639 A CN 1438639A CN 03104386 A CN03104386 A CN 03104386A CN 03104386 A CN03104386 A CN 03104386A CN 1438639 A CN1438639 A CN 1438639A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
- G11B7/2472—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes cyanine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Indole Compounds (AREA)
Abstract
To provide an optical recording material containing a cyanine compound in accordance with an optical recording medium which can cope with high speed recording. The optical recording material is used in the optical recording layer of the optical recording medium in which the layer is formed on a substrate and contains a compound expressed by formula (I) or formula (II) (the ring A and the ring B are each a benzene or naphthalene ring which can have a substituent; R1 is a 1-4C alkyl group; R2 and R3 are each a 1-4C alkyl group, a benzyl group, or a group forming a 3-4-membered ring by being connected; X is a hydrogen atom, a halogen atom, a 1-4C alkyl group, a phenyl group which can have a substituent, a benzyl group which can have a substituent, or a cyano group; Y1 and Y2 are independently an organic group; Anm- is an m-valent anion; m is 1 or 2; and (p) is a coefficient keeping the charge neutral).
Description
Technical field
The present invention relates to the optical recording material that in the optical recording medium thing of recorded information, uses by giving as the information pattern of heat by laser etc., more particularly, relate at the low laser of the wavelength by having visual and near infrared region and energy etc. and carry out the optical recording material that uses in highdensity optical recording and the reproducible optical recording medium thing.
Background technology
The optical recording medium thing have usually memory capacity big, write down or good feature such as reproduction in the noncontact mode, so be able to extensively popularize.WORM, CD-R, DVD-R etc. write troactively in the CD of type, make laser focusing on the pettiness area of optical recording layer, and the proterties that changes optical recording layer is carried out record, and by reproducing with the different of reflection light quantity of non-recorded part.
In the optical recording layer of optical recording medium thing that with the CD is representative, in order to be easy to form optical recording layer, make the organic system pigment, particularly cyanines based compound sensitivity height can be adapted to high speed, so study always.
Now, in above-mentioned CD, writing down and reproduce used Wavelength of Laser and be, is 750～830 nanometers to CD-R, is 620～690 nanometers to DVD-R.And, also developing the following CD of more highdensity 600 nanometers.The cyanines based compound that is adapted to these CDs for example has report in following document: the spy opens clear 59-55795 communique, and the spy opens flat 5-173282 communique, spy and opens flat 10-278426 communique, spy and open flat 11-53761 communique, spy and open flat 11-170695 communique, spy and open flat 11-227331 communique, spy and open flat 11-277904 communique, spy and open that flat 11-34499 communique, spy are opened the 2000-108510 communique, the spy opens flat 2000-289335 communique, special table 2001-506933 communique etc.
But above-mentioned cyanines based compound has problems aspect thermal decomposition characteristic.It is little to require heat to interfere when high-speed record.As optical recording material, though decomposition temperature is low and rapid being fit to of thermal decomposition, the various cyanines based compounds of above-mentioned report do not have sufficient feature in this respect.
Summary of the invention
Therefore, the purpose of this invention is to provide the optical recording material that contains the cyanines based compound that is consistent with the optical recording medium thing that can be adapted to high-speed record.
Present inventors etc. consider that suitableization of thermal decomposition effect and suitableization of absorbing wavelength are effective for the sensitivity that realization can be adapted to high-speed record, carried out research repeatedly, found that the cyanines based compound with specific molecular structure can solve above-mentioned problem, has obtained the present invention thus.
In the formula, ring A and ring B represent to have substituent phenyl ring or naphthalene nucleus, and R1 represents that carbon number is 1～4 alkyl; R2, R3 represent that carbon number is the group of 1～4 alkyl, the benzyl or 3～6 yuan of rings of formation that are connected; X represents that hydrogen atom, halogen atom, carbon number are 1～4 alkyl, can have substituent phenyl, can have substituent benzyl or cyano group; Y1 and Y2 represent organic group, An independently of one another
M-The negative ion of expression m valency, m represents 1 or 2 integer, it is neutral coefficient that p represents to keep electric charge.
The present invention can provide the optical recording material that contains the cyanines based compound that is consistent with the optical recording medium thing that can be adapted to high-speed record.
Embodiment
Below, embodiments of the present invention are described in detail.
Of the present invention by above-mentioned general formula (I) or (II) feature of cyanines based compound of expression be, have benzyl at specific position, lower than the decomposition temperature of other cyanines based compound that uses in optical recording material, absorbing wavelength is suitable.
In addition, Te Kaiping 5-173282 communique, spy open that flat 10-278426 communique, spy are opened flat 11-227331 communique, the spy opens in the flat 11-277904 communique, disclose partly contain of the present invention by the above-mentioned general formula (I) or (II) general formula of the general cyanines based compound of the compound of expression.In these reports, though put down in writing the substituent aralkyl of conduct of bonding on 3 of indoles skeleton, example does not illustrate benzyl particularly, does not put down in writing relevant benzyl, the method for aralkyl importing cyanines based compound, the effect of benzyl yet.
At above-mentioned general formula (I) with (II), the substituting group that can have substituent phenyl ring or naphthalene nucleus as being represented by ring A and ring B can list: halogeno-groups such as fluorine, chlorine, bromine, iodine; Alkyl such as methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, isobutyl, amyl group, isopentyl, tertiary pentyl, hexyl, cyclohexyl, heptyl, different heptyl, uncle's heptyl, n-octyl, iso-octyl, uncle's octyl group, 2-ethylhexyl; Aryl such as phenyl, naphthyl, 2-aminomethyl phenyl, 3-aminomethyl phenyl, 4-aminomethyl phenyl, 4-ethenylphenyl, 3-isopropyl phenyl; Alkoxys such as methoxyl, ethoxy, propoxyl group, isopropoxy, butoxy, sec-butoxy, tert-butoxy; Alkyl sulfenyls such as methyl mercapto, ethylmercapto group, rosickyite base, different rosickyite base, butylthio, secondary butylthio, uncle's butylthio; Nitro, cyano group etc.As the carbon number of being represented by R1 is 1～4 alkyl, can list: methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, isobutyl etc.As the carbon number of being represented by R2 and R3 is 1～4 alkyl, can list: methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, isobutyl etc.The group that links 3～6 yuan of rings that form as R2 and R3, can list: trimethylene-1,1-two bases, cyclo-butane-1,1-two bases, 2,4-dimethyl cyclo-butane-1,1-two bases, 3-dimethyl cyclo-butane-1,1-two bases, cyclopentane-1,1-two bases, cyclohexane-1,1-two bases, oxinane-4,4-two bases, thiazole-4,4-two bases, piperidines-4,4-two bases, N-substituted piperidine-4,4-two bases, morpholine-2,2-two bases, morpholine-3,3-two bases, N-substituted piperidine-2,2-two bases, N-substituted piperidine-3,3-two bases etc.As this N-substituting group, can list by the ring A illustrated those.
In addition, as the halogen atom of representing by X, can list: fluorine, chlorine, bromine, iodine etc.; As carbon number is 1～4 alkyl, can list: methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, isobutyl etc.As the substituting group of phenyl, benzyl, comprise encircling those cited substituting groups of A etc.As the organic group of representing by Y1 or Y2, do not limit especially, for example alkyl such as methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, isobutyl, amyl group, isopentyl, tertiary pentyl, hexyl, cyclohexyl, cyclohexyl methyl, 2-cyclohexyl ethyl, heptyl, different heptyl, uncle's heptyl, n-octyl, iso-octyl, uncle's octyl group, 2-ethylhexyl, nonyl, different nonyl, decyl, dodecyl, tridecyl, myristyl, pentadecyl, cetyl, heptadecyl, octadecyl; Vinyl, 1-methyl ethylene, 2-methyl ethylene, propenyl, butenyl group, isobutenyl, pentenyl, hexenyl, heptenyl, octenyl, decene base, ten pentaene bases, 1-phenyl propylene-alkenyls such as 3-base; Phenyl, naphthyl, 2-aminomethyl phenyl, 3-aminomethyl phenyl, 4-aminomethyl phenyl, 4-ethenylphenyl, 3-isopropyl phenyl, 4-isopropyl phenyl, 4-butyl phenyl, 4-isobutyl phenenyl, 4-tert-butyl-phenyl, 4-hexyl phenyl, 4-cyclohexyl phenyl, 4-octyl phenyl, 4-(2-ethylhexyl) phenyl, 4-stearoyl phenyl, 2,3-3,5-dimethylphenyl, 2,4-3,5-dimethylphenyl, 2,5-3,5-dimethylphenyl, 2,6-3,5-dimethylphenyl, 3,4-3,5-dimethylphenyl, 3,5-3,5-dimethylphenyl, 2, alkylaryls such as 4-di-tert-butyl-phenyl, cyclohexyl phenyl; Aryl alkyl such as benzyl, phenethyl, 2-phenyl-propane-2-base, diphenyl methyl, trityl group, styryl, cinnamyl and their alkyl are those groups that interrupted by ehter bond, thioether bond, for example can list: 2-methoxy ethyl, 3-methoxy-propyl, 4-methoxyl butyl, 2-butoxyethyl group, methoxyethoxyethyl, methoxy ethoxy ethoxyethyl group, 3-methoxyl butyl, 2-phenoxy group ethyl, 2-methylmercaptoethyl, 2-thiophenyl ethyl etc.And these groups can be by replacements such as alkoxy, alkenyl, nitro, cyano group, halogen atoms.
In addition, as by An
M-The negative ion of expression for example, as univalent anion, can list: halide anions such as cl anion, bromine anions, iodine negative ion, fluorine anion; Inorganic series anions such as perchloric acid negative ion, chloric acid negative ion, thiocyanic acid negative ion, phosphorus hexafluoride negative ion, antimony hexafluoride negative ion, tetrafluoride boron anion; Organic sulfonic acid negative ion such as benzene sulfonic acid negative ion, toluenesulfonic acid negative ion, trifluoromethayl sulfonic acid negative ion; Octyl group phosphate anion, dodecylphosphoric acid negative ion, octadecyl phosphate anion, phosphenylic acid negative ion, nonyl phenyl phosphate anion, 2, organic phospho acid series anions such as 2 '-di-2-ethylhexylphosphine oxide (4, the 6-di-tert-butyl-phenyl) phosphonic acids negative ion etc.; As dianion, for example can list: benzenedisulfonic acid negative ion, naphthalenedisulfonic acid negative ion etc.In addition, also can use as required and have the quencher negative ion that makes bioactive molecule deexcitation (quencher) function that is in excited state and metallocene compound negative ion such as the ferrocene that on the cyclopentadienyl ring, has anionic property groups such as carboxyl, phosphonate group, sulfonic group, ruthenocene etc.
Quencher negative ion as above-mentioned for example can list: by following general formula (A) or (B) expression, the spy opens clear 60-234892 communique, spy and opens flat 5-43814 communique, spy and open flat 6-239028 communique, spy and open the negative ion that flat 9-309886 communique, spy are opened record in the flat 10-45767 communique etc.
In the formula, M represents nickle atom or copper atom, R4 and R5 represent halogen atom, carbon number be 1～8 alkyl, carbon number be 6～30 aryl ,-SO
2-Z base, Z are represented alkyl, aryl, dialkyl amido, ammonia diaryl base, piperidyl, the morpholinyl that can be replaced by halogen atom; A and b represent 0～4 respectively; R6, R7, R8 and R9 represent alkyl, alkyl phenyl, alkoxyl phenyl and halogenophenyl independently of one another.
At above-mentioned general formula (I) or (II), for X, hydrogen atom is because be that thermal decomposition characteristic, particularly heat decomposition temperature are to be suitable for high-speed record, so be preferred.In addition, for Y1, the group identical with R1 is because manufacturing step is few, cost is low, so be preferred.For R2, R3, the group that forms 3～6 yuan of rings that is connected is to absorb ultraviolet ray, is particularly suitable for laser used in record, is preferred therefore.
O.1～51 concrete example as the compound by above-mentioned general formula (I) expression of the present invention can list following compound N.In addition, in following illustration, be to represent with having saved anionic cyanines kation.
In addition, as the concrete example of the compound of being represented by aforementioned formula (II), can list: the carbon number of above-mentioned illustrative compound N polymethine chain o.1～51 is 5 compound.
Above-mentioned of the present invention by above-mentioned general formula (I) or (II) the cyanines based compound of expression be not subjected to the restriction of its manufacture method.As the manufacture method of these cyanines based compounds, for example, under the R1 situation identical, can list following approach with Y1.And under the R1 situation different, can list with Y1: synthesize in hydrazine compound the material that imports Y1 in advance, then with it as raw material, with the approach of following same manufacturing.
In the formula, ring A, ring B, R1, R2, R3, X, Y2, An
M-, p is and aforementioned formula (I) or (II) same that D represents halogen, replaces sulfonyloxy.
As the halogen atom of representing by above-mentioned D, comprise chlorine, bromine, iodine etc.As replacing sulfonyloxy, comprise phenyl sulfonyloxy, 4-aminomethyl phenyl sulfonyloxy, 4-chlorphenyl sulfonyloxy etc.
Above-mentioned cyanines based compound as optical recording material of the present invention is suitable for the optical recording layer of making the optical recording medium thing, and the formation aspect of this optical recording layer does not limit especially.Generally speaking, can use the wet type rubbing method that on matrix, is coated with the solution that is dissolved in the following organic solvent by spin coating, spraying, impregnating: lower alcohols such as methyl alcohol, ethanol; Ether alcohol classes such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, butylene glycol; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol; Ester classes such as ethyl acetate, butyl acetate, acetic acid methoxyl ethyl ester; Esters of acrylic acid such as ethyl acrylate, butyl acrylate; 2,2,3, fluoro alcohols such as 3-tetrafluoropropanol; Hydro carbons such as benzene,toluene,xylene; Chlorinated hydrocarbons such as methylene chloride, ethylene dichloride, methenyl choloride etc.Other method comprises the method for steaming, sputtering method.
Normally 0.001～10 micron of the thickness of above-mentioned optical recording layer, preferably 0.01～5 micron scope.In addition, when containing optical recording material of the present invention in the optical recording layer of optical recording medium thing, this optical recording material is with respect to the consumption of this optical recording layer 50～100 weight % preferably.
In addition, except optical recording material of the present invention, can also contain as required in the above-mentioned optical recording layer: cyanines based compound, azo based compound, phthalocyanine based compound etc. can be used for the compound of optical recording layer; Can also contain: resenes such as tygon, polyester, polystyrene, polycarbonate; Surfactant; Charged preventor; Lubricant; Fire retardant; Free radical scavengers such as hindered amine; Pits such as ferrocene derivatives form promoter; Spreading agent; Antioxidant; Crosslinking chemical; Photostability imparting agent etc.
In addition, above-mentioned optical recording layer can contain the quencher as simple oxygen etc. such as aromatic nitro compound, amines, group with imine moiety, diimine compound, transition metal huge legendary turtle compound.They preferably use with the scope of 0～50 weight % with respect to optical recording layer.
The material that the matrix of such optical recording layer is set has no particular limits, so long as to writing (record) light and to read (reproduction) light be just transparent basically.For example, can use resins such as polymethylmethacrylate, polyethylene terephthalate, polycarbonate, glass etc.In addition, its shape can be used arbitrary shapes such as tape measure shape, reel, band shape, disk according to purposes.
In addition, on above-mentioned optical recording layer, also can use gold, silver, aluminium, copper etc. to form reflectance coating, also can pass through acryl resin, uv curing resin etc. and form protective seam by method of steaming or sputtering method.
Optical recording material of the present invention is applicable to the optical recording medium thing that uses semiconductor laser in record, reproduction.But, be particularly suitable in the CDs such as CD-R, DVD-R of high-speed record type.
Below, utilize Production Example, manufacturing embodiment, evaluation Example and embodiment to illustrate in greater detail the present invention.But, the invention is not restricted to following embodiment etc.
The manufacturing of Production Example 1 intermediate compound A
Drop into 39.7 gram 4-procarbazine hydrochlorides and 117.2 gram ethanol in the reaction flask of nitrogen replacement, simultaneously note heating down at 70 ℃ under stream of nitrogen gas, one side drips 40.8 gram 3-phenylethyl methyl ketone.Also Dropwise 35 % salt sour water 114.7 grams refluxed 2 hours.Cooling back adds 500 gram toluene and 500 gram water, adds 50% sodium hydrate aqueous solution again, makes pH reach more than 8 and carries out oil and water separation., dewater, desolventizing oil phase washing 3 times with 500 gram warm water.Residue to gained carries out partial crystallization with 117.2 gram ethanol, and the crystal of leaching gained carries out vacuum drying under 80 ℃, obtains 35.6 gram white crystals (yield 60.8%).White crystal, 28.4 gram iodomethane, the 19.6 gram methyl alcohol of 11.8 gram gained are fed in the reaction flask.In autoclave, reacted 5 hours in 100 ℃.Behind the desolventizing, adding 40 gram ethyl acetates also refluxed 30 minutes.After being cooled to room temperature, the leaching crystal.Under 80 ℃, carry out vacuum drying, obtain the yellow crystals 11.4 gram (yields: 58.3%) of intermediate A.
The manufacturing of Production Example 2 intermediate compound B
In the reaction flask of nitrogen replacement, drop into 34.9 gram 4-methoxyl hydrazinobenzene hydrochloride salts and 100 gram ethanol, under stream of nitrogen gas, simultaneously note heating down, a Dropwise 35 .6 gram 3-phenylethyl methyl ketone at 80 ℃.Reflux after 1 hour, drip sulfuric acid 5.9 grams, refluxed again 2 hours.Cooling back adds 200 gram toluene and 200 gram water, adds 50% sodium hydrate aqueous solution again, makes pH reach more than 8 and carries out oil and water separation., dewater, desolventizing oil phase washing 3 times with 200 gram warm water.Residue to gained carries out partial crystallization with 100 gram toluene, and the crystal of leaching gained carries out vacuum drying under 80 ℃, obtains 25.4 gram white crystals (yield 50.5%).White crystal, 28.4 gram iodomethane, the 19.6 gram methyl alcohol of 10.1 gram gained are fed in the reaction flask.In autoclave, reacted 5 hours in 100 ℃.Behind the desolventizing, adding 32.0 gram ethyl acetates also refluxed 30 minutes.After being cooled to room temperature, the leaching crystal.Under 80 ℃, carry out vacuum drying, obtain the yellow crystals 9.5 gram (yields: 58.3%) of intermediate B.
The manufacturing of Production Example 3 intermediate compound C
In the reaction flask of nitrogen replacement, drop into 79.1 gram 2-naphthylhydrazines and 274.1 gram ethanol, under stream of nitrogen gas, drip 3-phenylethyl methyl ketone 88.9 grams down at 55 ℃.Stir after 30 minutes, one side is noted heating, and one side drips 49 gram sulfuric acid, refluxes 1 hour.Cooling back adds 1000 gram toluene and 1000 gram water, adds 50% sodium hydrate aqueous solution again, makes pH reach more than 8 and carries out oil and water separation., dewater, desolventizing oil phase washing 3 times with 500 gram warm water.Residue to gained carries out partial crystallization with 137 gram toluene, and the crystal of leaching gained carries out vacuum drying under 80 ℃, obtains 72.4 gram white crystals (yield 53.4%).White crystal, 28.4 gram iodomethane, the 21.4 gram methyl alcohol of 13.6 gram gained are fed in the reaction flask.In autoclave, reacted 15 hours in 100 ℃.Behind the desolventizing, carry out partial crystallization with 100 gram ethyl acetates and 6.0 mixed solvents that restrain methyl alcohol.The leaching crystal.Under 140 ℃, carry out vacuum drying, obtain 6.9 gram (yields: the coarse crystal of intermediate C (HPLC purity 60%) 32.3%).
The manufacturing of Production Example 4 intermediate compound D
Drop into 157 gram phenylhydrazine sulfates and 221 gram ethanol in the reaction flask of nitrogen replacement, simultaneously note heating down at 70 ℃ under stream of nitrogen gas, one side drips 178 gram 3-phenylethyl methyl ketone.Drip 4.9 gram sulfuric acid again, refluxed 8 hours.Cooling back adds 250 gram toluene and 300 gram warm water, adds 50% sodium hydrate aqueous solution again, makes pH reach more than 8 and carries out oil and water separation., dewater, desolventizing oil phase washing 3 times with 300 gram warm water.Residue to gained carries out partial crystallization with 300 gram ethanol, and the crystal of leaching gained carries out vacuum drying under 80 ℃, obtains 116.1 gram white crystals (yield 52.5%).White crystal, 56.8 gram iodomethane, the 37.7 gram methyl alcohol of 22.1 gram gained are fed in the reaction flask, in autoclave, reacted 16 hours in 100 ℃.Behind the desolventizing, add 3.80 gram methyl alcohol and heating for dissolving, add 40 gram ethyl acetates and be cooled to room temperature again, carry out partial crystallization.The leaching crystal carries out vacuum drying under 80 ℃, obtain the white crystal 17.5 gram (yields: 46.4%) of intermediate D.
The manufacturing of Production Example 5 intermediate compound E
Drop into 19.0 gram 4-isopropyl hydrazinobenzene hydrochloride salts and 54.0 gram ethanol in the reaction flask of nitrogen replacement, simultaneously note heating down at 70 ℃ under stream of nitrogen gas, one side drips 18.1 gram 3-phenylethyl methyl ketone.Reflux after 1 hour, drip 2.0 gram sulfuric acid, refluxed again 1 hour.Cooling back adds 120 gram toluene and 120 gram water, adds 50% sodium hydrate aqueous solution again, makes pH reach more than 8 and carries out oil and water separation., dewater, desolventizing oil phase washing 3 times with 60.0 gram warm water.Residue to gained carries out partial crystallization with 100 gram toluene, and the crystal of leaching gained carries out vacuum drying under 80 ℃, obtains 18.1 gram Sandy crystal (yield 67.4%).Sandy crystal, 28.4 gram iodomethane, the 16.8 gram methyl alcohol of 10.5 gram gained are fed in the reaction flask, in autoclave, reacted 5 hours in 100 ℃.Behind the desolventizing, add 40.0 gram ethyl acetates and also refluxed 30 minutes, be cooled to room temperature after, the leaching crystal carries out vacuum drying under 80 ℃, obtain the yellow crystals 10.3 gram (yields: 59.6%) of intermediate E.
Make the o.4 manufacturing of phosphorus hexafluoride salt of embodiment 1 compound N
In the reaction flask of nitrogen replacement, the intermediate a that input 4.5 gram intermediate A, 3.9 grams are represented by following formula, 3.1 gram acetic anhydride and 15.8 gram pyridines, reaction is 3 hours under 50 ℃.Adding 50.0 gram methenyl cholorides, 50 gram water and 5.5 restrain the phosphorus hexafluoride potassium, stir 30 minutes and carried out salt to exchange.After removing water layer, add 50.0 gram water, add 1.0 gram phosphorus hexafluoride potassium again.After stirring 30 minutes, with the oil phase that 50.0 gram water washings are removed water 3 times, behind the anhydrous sodium sulfate drying, the decompression desolventizing is to obtain residue.In this residue, add 30.0 gram methyl alcohol to carry out partial crystallization, after the crystal of leaching is cleaned,, obtain green crystal 2.5 gram (yields: 38.9%) as the compound N phosphorus hexafluoride salt o.4 of object 140 ℃ of following vacuum drying.This crystal is carried out following analysis, confirm its structure etc.
Intermediate a
＜analysis result 〉
1. purity: HPLC measures; 99.3%
2. structure elucidation:
1H-NMR measures
(chemical shift ppm; Multiple degree; Proton number) (1.77; S; 3) (1.79; S; 3) (2.04; S; 3) (3.34; S; 3) (3.37～3.41; D; 1) (3.59～3.63; D; 1) (4.21; S; 3) (6.45～6.50; D; 1) (6.63～6.66; D; 2) (6.99～7.05; M; 3) (7.07～7.09; D; 1) (7.17～7.19; D; 1) (7.55; S; 1) (7.58～7.65; M; 2) (7.80～7.83; D; 1) (7.92～7.95; D; 1) (8.06～8.09; D; 1) (8.31～8.54; T; 1) (8.63～8.66; D; 1)
3. the characteristic of optics; Ultraviolet spectrogram with the methenyl choloride solvent is measured
λmax；593nm、ε；1.17×10
5
Make the o.7 manufacturing of phosphorus hexafluoride salt of embodiment 2 compound Ns
In the reaction flask of nitrogen replacement, drop into 4.1 and restrain intermediate B, 4.5 gram intermediate a, 3.1 gram acetic anhydride and 15.8 gram pyridines, reacted 3 hours down at 50 ℃.Adding 50.0 gram methenyl cholorides, 50.0 gram water and 5.5 restrain the phosphorus hexafluoride potassium, stir 30 minutes and carried out salt to exchange.After removing water layer, add 50.0 gram water, add 1.0 gram phosphorus hexafluoride potassium again.After stirring 30 minutes, with the oil phase that 50.0 gram water washings are removed water 3 times, behind the anhydrous sodium sulfate drying, the decompression desolventizing is to obtain residue.In this residue, add 100 gram methyl alcohol to carry out partial crystallization, after the crystal of leaching is cleaned,, obtain green crystal 2.4 gram (yields as the compound N phosphorus hexafluoride salt o.7 of object 140 ℃ of following vacuum drying; 35.7%).This crystal is carried out following analysis, confirm its structure etc.
＜analysis result 〉
1. purity; HPLC measures; 99.1%
2. structure elucidation;
1H-NMR measures
(chemical shift ppm; Multiple degree; Proton number) (1.83; S; 3) (2.00; S; 3) (2.06; S; 3) (3.49; S; 3) (3.55～3.58; D; 1) (3.69～3.72; D; 1) (3.89; S; 3) (4.34; S; 3) (6.56～6.60; D; 1) (6.66～6.69; D; 1) (6.79～6.80; D; 2) (6.95～6.97; D; 1) (7.02～7.09; M; 3) (7.12～7.15; D; 1) (7.36; S; 1) (7.58～7.66; M; 2) (7.75～7.77; D; 1) (7.91～7.93; D; 1) (8.06～8.08; D; 1) (8.68～8.78; T+d; 2)
3. the characteristic of optics: the ultraviolet spectrogram with the methenyl choloride solvent is measured
λmax；602nm、ε；1.09×10
5
Make the o.34 manufacturing of phosphorus hexafluoride salt of embodiment 3 compound Ns
In the reaction flask of nitrogen replacement, drop into 6.0 and restrain intermediate C, 1.4 gram N, N '-diphenyl amidine, 2.1 gram acetic anhydride and 11.1 gram pyridines reacted 2 hours down at 55 ℃.Add 20.0 gram methenyl cholorides, 40.0 gram water and 3.9 gram phosphorus hexafluoride potassium, stirred 30 minutes and carry out the salt exchange down at 50 ℃.After removing water layer, add 50.0 gram water, add 1.0 gram phosphorus hexafluoride potassium again, after stirring 30 minutes, with the oil phase that 40.0 gram water washings are removed water 3 times, behind the anhydrous sodium sulfate drying, the decompression desolventizing is to obtain residue.In this residue, add 40.0 gram methyl alcohol and carry out partial crystallization, with the crystal heating for dissolving of leaching at 5.0 gram N, in the dinethylformamide, again to wherein adding methyl alcohol to carry out crystallization again.After crystal cleaned,, obtain green crystal 0.6 gram (yield: 10.6%) as the compound N phosphorus hexafluoride salt o.34 of object 80 ℃ of following vacuum drying.This crystal is carried out following analysis, confirm its structure etc.
＜analysis result 〉
1. purity: HPLC measures; 98.0%
2. structure elucidation:
1H-NMR measures
(chemical shift ppm; Multiple degree; Proton number) (2.19; S; 6) (3.56; S; 6) (3.68～3.72; D; 2) (4.20～4.24; D; 2) (6.49～6.52; D; 4) (6.64～6.68; D; 2) (6.85～6.90; T; 6) (6.94～6.98; T; 2) (7.54～7.60; M; 4) (7.75～7.80; T; 2) (8.02～8.09; M; 4) (8.51～8.53; D; 2) (8.82～8.90; T; 3)
3. the characteristic of optics: the ultraviolet spectrogram with the methenyl choloride solvent is measured
λmax；608nm、ε；1.23×10
5
Make the o.36 manufacturing of phosphorus hexafluoride salt of embodiment 4 compound Ns
In the reaction flask of nitrogen replacement, drop into 7.5 and restrain intermediate D, 2.0 gram N, N '-diphenyl amidine, 3.1 gram acetic anhydride and 15.8 gram pyridines reacted 3 hours down at 60 ℃.Adding 25.0 gram methenyl cholorides, 25.0 gram water and 5.5 restrain the phosphorus hexafluoride potassium, stir 30 minutes and carried out salt to exchange.After removing water layer, add 25.0 gram water, add 1.0 gram phosphorus hexafluoride potassium again, after stirring 30 minutes, with the oil phase that 25.0 gram water washings are removed water 3 times, behind the anhydrous sodium sulfate drying, the decompression desolventizing is to obtain residue.In this residue, add 60.0 gram methyl alcohol and carry out partial crystallization.After the crystal of leaching cleaned,, obtain red crystals 2.2 gram (yields: 33.6%) as the compound N phosphorus hexafluoride salt o.36 of object 140 ℃ of following vacuum drying.This crystal is carried out following analysis, confirm its structure etc.
＜analysis result 〉
1. purity: HPLC measures; 100%
2. structure elucidation:
1H-NMR measures
(chemical shift ppm; Multiple degree; Proton number) (1.91; S; 6) (3.40～3.52; M+s; 2+6) (3.59～3.71; M; 2) (6.52～6.60; D; 2) (6.64～6.72; M; 4) (6.98～7.09; M; 6) (7.19～7.25; D; 2) (7.28～7.39; M; 4) (7.73～7.76; D; 2) (8.60～8.66; T; 1)
3. the characteristic of optics: the ultraviolet spectrogram with the methenyl choloride solvent is measured
λmax；561nm、ε；1.42×10
5
Make the o.41 manufacturing of phosphorus hexafluoride salt of embodiment 5 compound Ns
In the reaction flask of nitrogen replacement, intermediate b, 3.1 gram acetic anhydride and 15.8 gram pyridines that input 5.4 gram intermediate D, 3.8 grams are represented by following formula, reaction is 10 hours under 25 ℃.Heat after 50 ℃, adding 30.0 gram methenyl cholorides, 30.0 gram water and 5.5 restrain the phosphorus hexafluoride potassium, stir 30 minutes and carried out salt to exchange.After removing water layer, add 30.0 gram water, add 1.0 gram phosphorus hexafluoride potassium again, after stirring 30 minutes, with the oil phase that 30.0 gram water washings are removed water 3 times, behind the anhydrous sodium sulfate drying, the decompression desolventizing is to obtain residue.Add 2.0 gram N in this residue, add 20.0 gram methyl alcohol in the solution of dinethylformamide heating for dissolving and carry out partial crystallization, re-use 4.0 gram N, dinethylformamide and 20.0 gram methyl alcohol carry out crystallization again to the crystal of leaching.After the crystal that this mixed liquor of leaching is obtained is cleaned,, obtain strong green crystal 1.4 gram (yields: 20.9%) as the compound N phosphorus hexafluoride salt o.41 of object 140 ℃ of following vacuum drying.This crystal is carried out following analysis, confirm its structure etc.
Intermediate b
＜analysis result 〉
1. purity: HPLC measures; 90.0%
2. structure elucidation:
1H-NMR measures
(chemical shift ppm; Multiple degree; Proton number) (1.66～1.89; Br; 4) (1.80; S; 3) (2.49～2.62br+br; 4) (2.49～2.62; M; 2) (3.38; S; 3) (3.42～3.47; M; 2) (4.04; S; 3) (6.56～6.79; M; 4) (6.98～7.06; M; 3) (7.14～7.17; D; 1) (7.21～7.26; T; 1) (7.31～7.36; T; 1) (7.54～7.59; T; 1) (7.62～7.65; D; 1) (7.69～7.74; T; 1) (7.81～7.84; D; 1) (7.86～8.17; M; 2) (8.30～8.37; M; 2)
3. the characteristic of optics: the ultraviolet spectrogram with the methenyl choloride solvent is measured
λmax；579nm、ε；1.00×10
5
Make the o.43 manufacturing of phosphorus hexafluoride salt of embodiment 6 compound Ns
In the reaction flask of nitrogen replacement, the intermediate c that input 3.9 gram intermediate A, 4.9 grams are represented by following formula, 3.1 gram acetic anhydride and 15.8 gram pyridines, reaction is 3 hours under 50 ℃.Adding 50.0 gram methenyl cholorides, 50.0 gram water and 5.5 restrain the phosphorus hexafluoride potassium, stir 30 minutes and carried out salt to exchange.After removing water layer, add 50.0 gram water, add 1.0 gram phosphorus hexafluoride potassium again, after stirring 30 minutes, with the oil phase that 50.0 gram water washings are removed water 3 times, behind the anhydrous sodium sulfate drying, the decompression desolventizing is to obtain residue.In this residue, add 30.0 gram methyl alcohol and carry out partial crystallization, after the crystal of leaching is cleaned,, obtain green crystal 4.3 gram (yields: 62.9%) as the compound N phosphorus hexafluoride salt o.43 of object 140 ℃ of following vacuum drying.This crystal is carried out following analysis, confirm its structure etc.
Intermediate c
＜analysis result 〉
1. purity: HPLC measures; 99.3%
2. structure elucidation:
1H-NMR measures
(chemical shift ppm; Multiple degree; Proton number) (1.74～1.96; Br; 7) (2.09～2.19; Br; 6) (2.32; S; 3) (3.36; S; 3) (3.41～3.45; D; 1) (3.52～3.56; D; 1) (4.30; S; 3) (6.44～6.48; D; 1) (6.52～6.55; D; 1) (6.64～6.66; D; 2) (6.88～6.96; M; 4) (7.09～7.11; D; 1) (7.42; S; 1) (7.42～7.57; M; 2) (7.78～7.80; D; 1) (7.96～7.99; D; 2) (8.06～8.08; D; 1) (8.57～8.59; D; 1) (8.66～8.73; T; 1)
3. the characteristic of optics: the ultraviolet spectrogram with the methenyl choloride solvent is measured
λmax；596nm、ε；1.34×10
5
Make the o.44 manufacturing of phosphorus hexafluoride salt of embodiment 7 compound Ns
In the reaction flask of nitrogen replacement, drop into 4.2 and restrain intermediate E, 4.9 gram intermediate c, 3.1 gram acetic anhydride and 15.8 gram pyridines, reacted 3 hours down at 50 ℃.Adding 50.0 gram methenyl cholorides, 50.0 gram water and 5.5 restrain the phosphorus hexafluoride potassium, stir 30 minutes and carried out salt to exchange.After removing water layer, add 50.0 gram water, add 1.0 gram phosphorus hexafluoride potassium again, after stirring 30 minutes, with the oil phase that 50.0 gram water washings are removed water 3 times, behind the anhydrous sodium sulfate drying, the decompression desolventizing is to obtain residue.In this residue, add 30.0 gram methyl alcohol and carry out partial crystallization, after the crystal of leaching is cleaned,, obtain green crystal 3.3 gram (yields: 46.3%) as the compound N phosphorus hexafluoride salt o.44 of object 140 ℃ of following vacuum drying.This crystal is carried out following analysis, confirm its structure etc.
＜analysis result 〉
1. purity: HPLC measures; 99.5%
2. structure elucidation:
1H-NMR measures
(chemical shift ppm; Multiple degree; Proton number) (1.30～1.35; T; 6) (1.88～2.08; Br; 7) (2.24～2.34; Br; 6) (3.03～3.07; M; 1) (3.53～3.58; S+d; 4) (3.69～3.73; D; 1) (4.43; S; 3) (6.63～6.66; D; 1) (6.68～6.71; D; 1) (6.81～6.83; D; 2) (7.03～7.12; M; 4) (7.27～7.30; D; 1) (7.62～7.72; M; 3) (7.92～7.94; D; 1) (8.10～8.13; D; 1) (8.20～8.22; D; 1) (8.72～8.74; D; 1) (8.83～8.90; T; 1)
3. the characteristic of optics: the ultraviolet spectrogram with the methenyl choloride solvent is measured
λmax；597nm、ε；1.15×10
5
Make the manufacturing of embodiment 8 five first alkynes type cyanines based compounds
In the reaction flask of nitrogen replacement, the intermediate d that input 3.9 gram intermediate A, 4.5 grams are represented by following formula, 3.1 gram acetic anhydride and 15.8 gram pyridines, reaction is 10 hours under 25 ℃.Add 30.0 gram methenyl cholorides, 30.0 gram water and 5.5 gram phosphorus hexafluoride potassium, stirred 30 minutes and carried out the salt exchange at 50 ℃.After removing water layer, add 30.0 gram water, add 1.0 gram phosphorus hexafluoride potassium again, after stirring 30 minutes, with the oil phase that 30.0 gram water washings are removed water 3 times, behind the anhydrous sodium sulfate drying, the decompression desolventizing is to obtain residue.In this residue, add 45.0 gram methyl alcohol and carry out partial crystallization, after the crystal of leaching is cleaned,, obtain green crystal 4.7 gram (yields: 70.4%) as the compound N phosphorus hexafluoride salt o.52 of object 150 ℃ of following vacuum drying.This crystal is carried out following analysis, confirm its structure etc.
Intermediate d
＜analysis result 〉
1. purity: HPLC measures; 100%
2. structure elucidation:
1H-NMR measures
(chemical shift ppm; Multiple degree; Proton number) (1.79; S; 3) (1.96～1.99; D; 6) (2.40; S; 3) (3.28; S; 3) (3.48～3.52; D; 1) (3.66～3.70; D; 1) (3.73; S; 3) (6.22～6.26; D; 1) (6.31～6.36; D; 1) (6.55～6.63; M; 3) (6.95～7.05; M; 4) (7.13～7.15; D; 1) (7.48～7.50; T; 1) (7.58s; 1) (7.64～7.70; T; 1) (7.73～7.76; D; 1) (8.04～8.09; T; 2) (8.23～8.26; D; 1) (8.41～8.49; M; 2)
3. the characteristic of optics: the ultraviolet spectrogram with the methenyl choloride solvent is measured
λmax；667nm、ε；2.26×10
5
Evaluation Example
To the compound that obtains by above-mentioned manufacturing embodiment and the comparative compound 1～5 of the following stated, in stream of nitrogen gas, carry out differential thermal analysis, estimate the rapid property of heat decomposition temperature and thermal decomposition.Heat decomposition temperature is that the heating peak temperature by DTA compares evaluation, and sharply property is to decompose the temperature that ends and its width is estimated by DSC fusion～heating.The results are shown in table 1～4.
Comparative compound 4
Table 1
| Cyanines based compound kation | Cyanines based compound negative ion | Heat decomposition temperature (℃) | The rapid property of thermal decomposition (℃) | |
| Evaluation Example 1 | Compound N o.4 | ????PF 6 - | ????242.5 | ????8.5 |
| Evaluation Example 2 | Compound N o.7 | ????PF 6 - | ????247.5 | ????12.4 |
| Evaluation Example 3 | Compound N o.41 | ????PF 6 - | ????227.1 | ????9.8 |
| Evaluation Example 4 | Compound N o.43 | ????PF 6 - | ????252.2 | ????2.7 |
| Evaluation Example 5 | Compound N o.44 | ????PF 6 - | ????241.9 | ????13.9 |
| Comparative evaluation example 1 | Comparative compound 1 | ????PF 6 - | ????282.5 | ????19.5 |
| Comparative evaluation example 2 | Comparative compound 2 | ????PF 6 - | ????276.5 | ????25.0 |
Table 2
| Cyanines based compound kation | Cyanines based compound negative ion | Heat decomposition temperature (℃) | The rapid property of thermal decomposition (℃) | |
| Evaluation Example 6 | Compound N o.34 | ????PF 6 - | ????229.1 | ????1.0 |
| Comparative evaluation example 3 | Comparative compound 3 | ????PF 6 - | ????292 | ????2.0 |
Table 3
| Cyanines based compound kation | Cyanines based compound negative ion | Heat decomposition temperature (℃) | The rapid property of thermal decomposition (℃) | |
| Evaluation Example 7 | Compound N o.34 | ????PF 6 - | ????246.6 | ????4.2 |
| Comparative evaluation example 4 | Comparative compound 4 | ????PF 6 - | ????300 | ????10.8 |
Table 4
| Cyanines based compound kation | Cyanines based compound negative ion | Heat decomposition temperature (℃) | The rapid property of thermal decomposition (℃) | |
| Evaluation Example 8 | Compound N o.52 | ????PF 6 - | ????222.0 | ????50 |
| Comparative evaluation example 5 | Comparative compound 5 | ????PF 6 - | ????247.0 | ????64.3 |
Can confirm that from the result of above-mentioned table 1～4 of the present invention is to decompose at low temperatures at 3 cyanines based compounds that imported benzyl, the rapid property of thermal decomposition also is good.These character are suitable for high-speed record.
The manufacturing and the evaluation of embodiment 1～6 recording medium thing
At coating titanium chelant compounds (T-50: Japanese Cao Da corporate system), thereby add diameter that water decomposition forms base coating and be on 12 centimetres the polycarbonate disk substrate, by 2,2,3,3-tetrafluoropropanol solution (concentration 2%) is coated with by making embodiment 1～3,5 by spin-coating method, the cyanines based compound that 7-8 obtains obtains forming the optical recording medium thing of the optical recording layer of thickness 100 nanometers.At this moment, by the record light wavelength of using in the optical recording disk mensuration that these optical recording medium things carry out the ultraviolet spectrogram absorption is estimated.The intensity of the λ max of each recording medium thing as 1, is lower than at 0.15 o'clock with respect to this value of relative intensity, record and the characteristic degradation that reproduces, and surpass at 0.50 o'clock, the photostability variation of optical recording layer, the maintenance bad stability of record.Therefore, relative intensity is shown as the recording light wavelength of 0.15～0.50 optimum range as suitable recording light wavelength.The result remembers in table 5.
Table 5
| Cyanine compound | λ max nanometer | Suitable recording light wavelength (relative intensity) | |
| Embodiment 1 | Compound N is PF o.4 6 -Salt | ??610 | 635 nanometers (0.477), 650 nanometers (0.208) |
| Embodiment 2 | Compound N is PF o.7 6 -Salt | ??619 | 650 nanometers (0.305), 660 nanometers (0.188) |
| Embodiment 3 | Compound N is PF o.34 6 -Salt | ??620 | 650 nanometers (0.316), 660 nanometers (0.181) |
| Embodiment 4 | Compound N is PF o.41 6 -Salt | ??594 | 620 nanometers (0.444), 635 nanometers (0.180) |
| Embodiment 5 | Compound N is PF o.44 6 -Salt | ??610 | 635 nanometers (0.455), 650 nanometers (0.200) |
| Embodiment 6 | Compound N is PF o.52 6 -Salt | ??706 | 770 nanometers (0.292), 780 nanometers (0.180), 790 nanometers (0.151) |
Claims (5)
1, a kind of optical recording material, it contains: on matrix, form use in the described optical recording layer of optical recording medium thing of optical recording layer, by the following general formula (I) or (II) compound of expression
In the formula, ring A and ring B represent to have substituent phenyl ring or naphthalene nucleus, and R1 represents that carbon number is 1～4 alkyl; R2, R3 represent that carbon number is the group of 1～4 alkyl, the benzyl or 3～6 yuan of rings of formation that are connected; X represents that hydrogen atom, halogen atom, carbon number are 1～4 alkyl, can have substituent phenyl, can have substituent benzyl or cyano group; Y1 and Y2 represent organic group, An independently of one another
M-The negative ion of expression m valency, m represents 1 or 2 integer, it is neutral coefficient that p represents to keep electric charge.
2, optical recording material as claimed in claim 1, wherein at above-mentioned general formula (I) or (II), R2, R3 are connected to form the group of 3～6 yuan of rings.
3, optical recording material as claimed in claim 1 or 2, wherein X is a hydrogen atom at above-mentioned general formula (I) or (II).
4, as the described optical recording material of one of claim 1～3, wherein Y1 is the group identical with R1 at above-mentioned general formula (I) or (II).
5, a kind of optical recording medium thing, it is to form by the film that constitutes as the described optical recording material of one of claim 1～4 on matrix.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2002033599A JP3659922B2 (en) | 2002-02-12 | 2002-02-12 | Optical recording material |
| JP200233599 | 2002-02-12 |
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| KR (1) | KR100814215B1 (en) |
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Also Published As
| Publication number | Publication date |
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| KR100814215B1 (en) | 2008-03-17 |
| TWI359146B (en) | 2012-03-01 |
| JP3659922B2 (en) | 2005-06-15 |
| KR20030068414A (en) | 2003-08-21 |
| CN1266693C (en) | 2006-07-26 |
| TWI341858B (en) | 2011-05-11 |
| JP2003231359A (en) | 2003-08-19 |
| TW201035080A (en) | 2010-10-01 |
| TW200306334A (en) | 2003-11-16 |
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