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WO2010041691A1 - Support d’enregistrement optique contenant un complexe métallique de composé de squarylium - Google Patents

Support d’enregistrement optique contenant un complexe métallique de composé de squarylium Download PDF

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Publication number
WO2010041691A1
WO2010041691A1 PCT/JP2009/067508 JP2009067508W WO2010041691A1 WO 2010041691 A1 WO2010041691 A1 WO 2010041691A1 JP 2009067508 W JP2009067508 W JP 2009067508W WO 2010041691 A1 WO2010041691 A1 WO 2010041691A1
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group
substituent
compound
optionally substituted
hydrogen atom
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English (en)
Japanese (ja)
Inventor
貴弘 澤田
竜生 新見
豊田　浩
一太 服部
尚志 沖村
辻田　公二
山下　智
大嶋　克則
宇航 須本
栄治 中川
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Victor Company of Japan Ltd
KH Neochem Co Ltd
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Kyowa Hakko Chemical Co Ltd
Victor Company of Japan Ltd
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Priority to JP2010532944A priority Critical patent/JPWO2010041691A1/ja
Publication of WO2010041691A1 publication Critical patent/WO2010041691A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/007—Squaraine dyes
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
    • 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
    • G11B7/249—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 organometallic compounds

Definitions

  • the present invention relates to an optical recording medium containing a metal complex of a squarylium compound.
  • an optical recording medium that enables ultra-high density recording using a technique for increasing the numerical aperture NA of the objective lens, a technique for reducing the laser wavelength ⁇ , and the like has been progressing.
  • an optical recording medium having the same size as a DVD and a capacity of at least 23 GB is required.
  • an optical recording medium that records higher density information by using a 405 nm blue-violet laser, setting the NA of the objective lens to 0.85, and reducing the laser spot diameter, so-called Blu-ray Disc (BD) has been developed.
  • BD Blu-ray Disc
  • the write-once Blu-ray Disc (BD-R) is required to have various excellent characteristics in terms of recording sensitivity, modulation degree, jitter (jitter), error rate, etc., in addition to the required performance that enables recording and playback. .
  • BD-R write-once Blu-ray Disc
  • modulation degree modulation degree
  • jitter jitter
  • error rate etc.
  • those properties in BD-R using conventional organic dyes are not sufficient.
  • a metal complex of a squarylium compound having a pyrazole structure is useful as a dye used for a write-once digital versatile disk (DVD-R) (Patent Document 1).
  • the dye is suitable for recording with a laser beam of about 650 nm used for DVD-R recording, but is not suitable for recording with a laser beam of 405 nm.
  • a metal complex of a squarylium compound having a pyrazole structure and an amine structure is useful as a dye for a filter for an electronic display device (Patent Document 2).
  • An object of the present invention is to provide an optical recording medium or the like using a metal complex of a squarylium compound having a highly sensitive photoresponsiveness to blue-violet laser light.
  • the present invention provides the following [1] to [12].
  • R 1 represents a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an alicyclic hydrocarbon group which may have a substituent, An aryl group which may have a substituent or a heterocyclic group which may have a substituent
  • R 2 represents a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen atom, a nitro group, a cyano group, a substituent
  • R 3 and R 4 may be the same or different and each may have a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent.
  • An alicyclic hydrocarbon group, an optionally substituted aryl group or an optionally substituted heterocyclic group, or R 3 and R 4 together with the adjacent nitrogen atom The optical recording medium according to [1], wherein an alicyclic heterocyclic ring optionally having a substituent is formed.
  • R 5 and R 6 are represented by the formula (II): [Wherein W is a nitrogen atom or C—R 7 (wherein R 7 is a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen atom, a nitro group, a cyano group, an amino group which may have a substituent, An alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aralkyl group which may have a substituent, and an alicyclic hydrocarbon which may have a substituent A group, an aryl group which may have a substituent or a heterocyclic group which may have a substituent, and X represents a nitrogen atom or C—R 8 (wherein R 8 represents the above R 7 represents a nitrogen atom or C—R 9 (wherein R 9 is as defined above for R 7 ), and Z represents a nitrogen atom or C—R 10 (wherein R 7 10 represents a a
  • optical recording medium according to [3] or [4].
  • [6] The optical recording medium according to [5], wherein W is a nitrogen atom, X is CR 8 , Y is CR 9 , and Z is CR 10 .
  • [7] The optical recording medium according to [5] or [6], wherein one of R 5 and R 6 is the formula (II) and the other is a hydrogen atom.
  • R 1 and R 2 may be the same or different and each may have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent.
  • optical recording medium according to any one of [1] to [8], wherein the metal is nickel, cobalt, aluminum, copper, zinc, or iron.
  • metal is nickel or cobalt.
  • R 1 represents a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, an alicyclic hydrocarbon group which may have a substituent, An aryl group which may have a substituent or a heterocyclic group which may have a substituent
  • R 2 represents a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen atom, a nitro group, a cyano group, a substituent
  • R 9 and R 10 represent an aryl group or an optionally substituted heterocyclic group
  • X represents a nitrogen atom or C—R 8 (wherein R 8 has the same meaning as R 7 above)
  • Y represents Represents a nitrogen atom or C—R 9 (wherein R 9 is as defined above for R 7 )
  • Z is Nitrogen atom or C-R 10 (wherein, R 10 is a is same meaning as the R 7) represents, W is the C-R 7 a and X are each R 7 and R 8 when it is C-R 8
  • a hydrocarbon ring which may have a substituent may be formed together with two adjacent carbon atoms
  • R 8 and R 9 may be combined with two adjacent carbon atoms to form a hydrocarbon ring which may have a substituent
  • Y is C—R 9 and Z is C—R 10 .
  • R 9 and R 10 may be combined with two adjacent nitrogen atoms to form a hydrocarbon ring which may have
  • an optical recording medium using a metal complex of a squarylium compound having a highly sensitive photoresponsiveness to blue-violet laser light.
  • Compound (I) the compound represented by Formula (I) is referred to as Compound (I). The same applies to the compounds of other formula numbers.
  • examples of the alkyl moiety in the alkyl group and the alkoxyl group include a linear or branched alkyl group having 1 to 20 carbon atoms, specifically, a methyl group, an ethyl group, and the like.
  • An octyl group, a nonyl group, a decyl group, an eicosyl group and the like can be mentioned. Among them, those having 1 to 6 carbon atoms are preferable.
  • aralkyl group examples include an aralkyl group having 7 to 15 carbon atoms, and specific examples include a benzyl group, a phenethyl group, a phenylpropyl group, and a naphthylmethyl group.
  • aryl group examples include aryl groups having 6 to 14 carbon atoms, and specific examples include a phenyl group, a naphthyl group, an anthryl group, and an azulenyl group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the alicyclic hydrocarbon in the alicyclic hydrocarbon group include, for example, a cycloalkane having 3 to 8 carbon atoms, a cycloalkene having 3 to 8 carbon atoms, and a bicyclic or tricyclic condensed 3- to 8-membered ring. And alicyclic hydrocarbons.
  • cycloalkane having 3 to 8 carbon atoms include, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane and the like.
  • C3-C8 cycloalkene examples include, for example, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene and the like.
  • bicyclic or tricyclic alicyclic hydrocarbon condensed with a 3- to 8-membered ring include dihydropentalene, dihydroindene, tetrahydronaphthalene, hexahydrofluorene and the like.
  • heterocyclic ring in the heterocyclic group examples include an aromatic heterocyclic ring and an alicyclic heterocyclic ring.
  • aromatic heterocyclic ring for example, a 5- or 6-membered monocyclic aromatic heterocyclic ring containing at least one atom selected from a nitrogen atom, an oxygen atom and a sulfur atom is condensed.
  • bicyclic or tricyclic condensed aromatic heterocycles containing at least one atom selected from a nitrogen atom, an oxygen atom, and a sulfur atom.
  • Specific examples include a pyridine ring, a pyrazine ring, and a pyrimidine ring.
  • alicyclic heterocycle for example, a 5- to 8-membered monocyclic alicyclic heterocycle containing at least one atom selected from a nitrogen atom, an oxygen atom and a sulfur atom is condensed.
  • a bicyclic or tricyclic condensed alicyclic heterocyclic ring containing at least one atom selected from a nitrogen atom, an oxygen atom and a sulfur atom specifically, a pyrrolidine ring, a piperidine ring
  • Examples include piperazine ring, morpholine ring, thiomorpholine ring, homopiperidine ring, homopiperazine ring, tetrahydropyridine ring, tetrahydroquinoline ring, tetrahydroisoquinoline ring, tetrahydrofuran ring, tetrahydropyran ring, dihydrobenzofuran ring, tetrahydrocarbazole ring and the like.
  • Examples of the alicyclic heterocycle formed by combining R 3 and R 4 with the adjacent nitrogen atom include those containing at least one nitrogen atom among the above alicyclic heterocycles. Specific examples include pyrrolidine ring, piperidine ring, piperazine ring, morpholine ring, thiomorpholine ring, homopiperidine ring, homopiperazine ring, tetrahydropyridine ring, tetrahydroquinoline ring, tetrahydroisoquinoline ring and the like.
  • Examples of the hydrocarbon ring formed by combining R 7 and R 8 , R 8 and R 9 , or R 9 and R 10 together with two adjacent carbon atoms include, for example, non-carbon atoms of 5 to 10 carbon atoms.
  • Examples include saturated hydrocarbon rings, and specific examples include a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, a cyclooctene ring, a benzene ring, and a naphthalene ring.
  • substituents for the alkyl group and the alkoxyl group include, for example, the same or different 1 to 5 substituents, specifically, a hydroxyl group, a carboxyl group, a halogen atom, a nitro group, a cyano group, an alkoxyl group, an alkoxyalkoxyl.
  • substituents specifically, a hydroxyl group, a carboxyl group, a halogen atom, a nitro group, a cyano group, an alkoxyl group, an alkoxyalkoxyl.
  • the halogen atom, the heterocyclic group, and the alkoxyl group have the same meanings as described above.
  • the two alkoxy moieties of the alkoxyalkoxyl group have the same meaning as the above alkoxyl group, respectively.
  • the alkyl portions of the alkanoyl group, alkylcarbonyloxy group and alkoxycarbonyl group are as defined above.
  • the aryl part of the aroyl group, aryloxy group, arylcarbonyloxy group and aryloxycarbonyl group has the same meaning as the above aryl group.
  • substituent of the amino group examples include one or two substituents, specifically, an alkyl group, an aralkyl group, an alicyclic hydrocarbon group, an aryl group, and the like.
  • alkyl group, the aralkyl group, the alicyclic hydrocarbon group, and the aryl group have the same meanings as described above.
  • each of the substituents may be the same or different.
  • substituent of the aralkyl group, alicyclic hydrocarbon group, and aryl group include, for example, the same or different 1 to 5 substituents, specifically, a hydroxyl group, a carboxyl group, a halogen atom, a nitro group, Cyano group, optionally substituted alkyl group, optionally substituted alkoxyl group, aralkyl group, alkanoyl group, alkylcarbonyloxy group, alkoxycarbonyl group, aryl group, aroyl group, aryloxy Group, an arylcarbonyloxy group, an aryloxycarbonyl group, a heterocyclic group, an amino group which may have a substituent, and the like.
  • a halogen atom an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aralkyl group, an alkanoyl group, an alkylcarbonyloxy group, an alkoxycarbonyl group, an aryl group, an aroyl group , Aryloxy group, arylcarbonyloxy group, aryloxycarbonyl group, heterocyclic group and optionally substituted amino group have the same meanings as described above.
  • Examples of the substituent of the heterocyclic group when R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 or R 10 is a heterocyclic group include, for example, an aralkyl group and an alicyclic hydrocarbon Examples of the group and the substituent of the aryl group include the same functional groups exemplified above.
  • Examples of the substituent of the heterocyclic group when R 5 , R 6 or R 5a is a heterocyclic group may include a hydroxyl group, a carboxyl group, a halogen atom, a nitro group, a cyano group, and a substituent.
  • Examples thereof include a cyclic hydrocarbon group, an aryl group which may have a substituent, and a heterocyclic group which may have a substituent.
  • a halogen atom an amino group which may have a substituent, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or a substituent.
  • a good aralkyl group, an alicyclic hydrocarbon group which may have a substituent and an aryl group which may have a substituent have the same meanings as described above, and an optionally substituted heterocycle
  • the group has the same meaning as that when R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 or R 10 is a heterocyclic group which may have a substituent.
  • Examples of the substituent for the alicyclic heterocyclic ring formed by combining R 3 and R 4 with the adjacent nitrogen atom include those exemplified above as the substituent for the aralkyl group, alicyclic hydrocarbon group, and aryl group. And the same functional groups as those described above.
  • Examples of the substituent of the hydrocarbon ring formed by R 7 and R 8 , R 8 and R 9 , or R 9 and R 10 together with two adjacent carbon atoms include aralkyl groups, Examples of the substituent of the cyclic hydrocarbon group and aryl group are the same as the functional groups exemplified above.
  • Examples of the metal in the metal complex include aluminum, ruthenium, osmium, iron, platinum, zinc, beryllium, copper, nickel, chromium, cobalt, manganese, iridium, vanadium, titanium, etc., among which nickel, cobalt, aluminum, Copper, zinc and iron are preferred.
  • compound (I) when at least one of R 3 and R 4 is NR 5 R 6 , one of R 3 and R 4 is NR 5 R 6 , the other is a hydrogen atom, and R 5 and R 4 It is preferable that one of 6 is the formula (II) and the other is a hydrogen atom.
  • formula (II) is as defined above.
  • R 5a is preferably a hydrogen atom.
  • Compound (I) is, for example, reaction formula (a): (Wherein R 1 , R 2 , R 3 and R 4 are as defined above). Specifically, the compound (III) or a salt thereof and the compound (IV) or a salt thereof, if necessary, in the presence of an acid catalyst in an amount of 0.1 to 1.5-fold moles relative to the compound (III)
  • the compound (I) can be produced by reacting at 40 to 140 ° C. for 0.5 to 30 hours.
  • the amount of compound (IV) or a salt thereof used is preferably 1 to 5 times the molar amount relative to compound (III) or a salt thereof.
  • reaction temperature is preferably 40 to 100 ° C.
  • R 3 and R 4 are the same or different and are each a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an alicyclic which may have a substituent.
  • the reaction temperature is preferably 80 to 140 ° C.
  • the aryl group and the heterocyclic group which may have a substituent are as defined above.
  • Examples of the salt of compound (III) include potassium salt and sodium salt.
  • Examples of the salt of compound (IV) include hydrochloride, sulfate, p-toluenesulfonate, methanesulfonate, and the like.
  • Examples of the acid catalyst include sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid and the like.
  • Compound (III) is a diester of squaric acid or a dihalide of squaric acid and a compound of formula (V): (Wherein R 1 and R 2 have the same meanings as described above), and a compound represented by the known method, for example, the method described in WO 01/44233 pamphlet or the like. Can be obtained.
  • Compound (V) can be obtained as a commercial product or can be obtained by publicly known methods, for example, the Chemical Society of Japan, New Experimental Chemistry Course, Volume 14, “Synthesis and Reaction of Organic Compounds IV Heterocyclic Compounds”, Maruzen Co., Ltd. Company, 1978, p. 2154, Chemistry, 1964, 26, p. 333, Journal of Organic Chemistry, 1957, Vol. 22, p.
  • a compound (IV) in which at least one of R 3 and R 4 is NR 5 R 6 (wherein R 5 and R 6 have the same meanings as described above) is obtained as a commercial product, Known methods, for example, Journal of Medical Chemistry, 1985, Vol. 28, p. It can be obtained by manufacturing according to the method described in 1394 or the like.
  • R 3 and R 4 in the compound (IV) are the same or different and have a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent.
  • An alicyclic hydrocarbon group that may be substituted, an aryl group that may have a substituent, or a heterocyclic group that may have a substituent (provided that R 3 and R 4 simultaneously represent a hydrogen atom; May be obtained as a commercial product or may be obtained by a known method such as JP-A-48-39454, JP-A-63-253056, WO95 / 7888, Tetrahedron, 2005. Year, Vol. 61, No. 24, p.
  • an alkyl group which may have a substituent an aralkyl group which may have a substituent, an alicyclic hydrocarbon group which may have a substituent, and a substituent.
  • the aryl group and the heterocyclic group which may have a substituent are as defined above.
  • the solvent examples include alcohol solvents such as ethanol, propanol, 2-propanol, butanol and octanol, a mixed solvent of the alcohol solvent (20% by volume or more) and benzene, toluene or xylene, acetonitrile and the like.
  • alcohol solvents such as ethanol, propanol, 2-propanol, butanol and octanol
  • Compound (Ia) can be produced according to the production method of compound (I).
  • the metal complex of compound (I) can be produced according to a known method, for example, the method described in International Publication No. 02/050190 pamphlet or the like. Specifically, the organometallic compound or metal salt and the compound (I) are optionally added at 25 to 120 ° C. in a solvent in the presence of 1 to 5 moles of acetic acid with respect to the organometallic compound or metal salt.
  • the metal complex of compound (I) can be produced by reacting at a temperature of 0.1 to 30 hours.
  • the amount of compound (I) used is preferably 0.5 to 5 times the molar amount of the organometallic compound or metal salt.
  • organometallic compound examples include aluminum tris (acetylacetonate), aluminum tris (ethylacetoacetate), aluminum isopropoxide, aluminum sec-butoxide, aluminum ethoxide, copper acetylacetonate, zinc acetylacetonate, iron tris. (2,4-pentanedionate), tris (carbonate) cobalt (III) sodium salt, and the like.
  • metal salt examples include aluminum chloride, copper chloride, copper acetate, nickel acetate, nickel chloride, cobalt acetate, cobalt chloride, and hydrates thereof.
  • the solvent examples include alcohol solvents such as methanol, ethanol, propanol, 2-propanol, butanol and isobutanol, halogen solvents such as chloroform and dichloromethane, aromatic solvents such as benzene, toluene and xylene, tetrahydrofuran and methyl.
  • alcohol solvents such as methanol, ethanol, propanol, 2-propanol, butanol and isobutanol
  • halogen solvents such as chloroform and dichloromethane
  • aromatic solvents such as benzene, toluene and xylene
  • tetrahydrofuran and methyl examples include ether solvents such as -tert-butyl ether, ester solvents such as ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, and mixed solvents thereof.
  • the metal complex of compound (I) may be purified by methods usually used in organic synthetic chemistry (various column chromatography methods, recrystallization methods, washing with a solvent, etc.).
  • the metal complex of compound (Ia) can be manufactured according to the manufacturing method of the metal complex of compound (I).
  • Me represents a methyl group
  • Et represents an ethyl group
  • n-Pr represents a propyl group
  • i-Pr represents an isopropyl group
  • n-Bu represents a butyl group
  • i-Bu represents an isobutyl group
  • T-Bu represents a tert-butyl group
  • Ph represents a phenyl group.
  • the metal complex of the compound (I) used in the present invention is a dye for optical recording media, an ultraviolet absorber, a two-photon absorption dye as a three-dimensional recording material, and an increase in response to short wavelength laser (for example, blue-violet laser). It can be used as a dye-sensitive dye.
  • the metal complex of compound (I) is suitable as a dye for an optical recording medium because it has excellent light resistance, excellent weather resistance, excellent moisture and heat resistance, excellent coating properties, and excellent solubility.
  • the optical recording medium of the present invention contains a metal complex of compound (I) and has high sensitivity photoresponsiveness to blue-violet laser light, excellent recording signal quality, and the like.
  • Examples of the optical recording medium of the present invention include a substrate, a reflective layer, a recording layer, a transparent protective layer and a cover layer. The reflective layer, the recording layer, the transparent protective layer and the cover are provided on the substrate. It is preferable that the layers are provided in this order.
  • Examples of the optical recording medium of the present invention include those having a recording layer containing a metal complex of compound (I). When the recording layer is formed using the metal complex of compound (I), the metal complex of compound (I) may be used alone or in admixture of two or more.
  • the metal complex of compound (I) and other dyes may be used in combination.
  • Other dyes preferably have absorption in the wavelength region of the recording laser light.
  • a dye that does not hinder the formation of information recording (recording marks, etc. formed at a laser irradiation site due to thermal deformation in the recording layer, the reflective layer or the transparent protective layer, and the cover layer) may be used as another dye. preferable.
  • dyes examples include metal-containing azo dyes, phthalocyanine dyes, naphthalocyanine dyes, cyanine dyes, azo dyes, squarylium dyes other than the metal complex of compound (I), metal-containing indoaniline dyes , Triarylmethane dyes, merocyanine dyes, azurenium dyes, naphthoquinone dyes, anthraquinone dyes, indophenol dyes, xanthene dyes, oxazine dyes, pyrylium dyes, and the like. You may use these individually or in mixture of 2 or more types.
  • a combination of a dye suitable for recording using a laser beam such as a near infrared laser beam of 770 to 830 nm and a red laser beam of 620 to 690 nm and a metal complex of compound (I) can be used at a plurality of wavelengths.
  • An optical recording medium capable of recording with a laser beam in the region can also be produced.
  • the recording layer may contain a binder as necessary.
  • the binder include polyvinyl alcohol, polyvinyl pyrrolidone, ketone resin, nitrocellulose, cellulose acetate, polyvinyl butyral, and polycarbonate. You may use these individually or in mixture of 2 or more types.
  • the recording layer may contain, for example, a singlet oxygen quencher, a recording sensitivity improver, etc. in order to improve the stability and light resistance of the recording layer.
  • the singlet oxygen quencher examples include transition metal chelate compounds (for example, chelate compounds of acetylacetonate, bisphenyldithiol, salicylaldehyde oxime, bisdithio- ⁇ -diketone, etc. and transition metal) and the like. You may use these individually or in mixture of 2 or more types.
  • transition metal chelate compounds for example, chelate compounds of acetylacetonate, bisphenyldithiol, salicylaldehyde oxime, bisdithio- ⁇ -diketone, etc. and transition metal
  • a compound in which a metal such as a transition metal is contained in a compound in the form of atoms, ions, clusters, etc. for example, an ethylenediamine complex, an azomethine complex, a phenylhydroxyamine complex, a phenanthroline complex, And organic metal compounds such as dihydroxyazobenzene complex, dioxime complex, nitrosoaminophenol complex, pyridyltriazine complex, acetylacetonate complex, metallocene complex and porphyrin complex. You may use these individually or in mixture of 2 or more types.
  • the thickness of the recording layer of the optical recording medium of the present invention is preferably 1 nm to 5 ⁇ m, more preferably 5 to 100 nm, and further preferably 20 to 60 nm.
  • the recording layer can be formed by a known thin film forming method such as a vacuum deposition method, a sputtering method, a doctor blade method, a cast method, a spin coating method, or an immersion method, but the spin coating method is preferable from the viewpoint of mass productivity and cost.
  • a solution in which the concentration of the metal complex of compound (I) is adjusted to 0.3 to 1.5% by weight is used, and the rotation speed is 500. It is preferable to set it to ⁇ 10000 rpm. After applying the solution by a spin coating method, treatment such as heating, drying under reduced pressure, or exposure to solvent vapor may be performed.
  • the solvent of the solution may be on the substrate before applying the substrate and the recording layer.
  • the solvent is not particularly limited as long as it is a solvent that does not attack the formed layer (for example, a reflective layer).
  • ketone alcohol solvents such as diacetone alcohol and 3-hydroxy-3-methyl-2-butanone
  • cellosolv solvents such as methyl cellosolve and ethyl cellosolve, n-hexane, n-octane, cyclohexane, methylcyclohexane, ethylcyclohexane
  • Hydrocarbon solvents such as dimethylcyclohexane, n-butylcyclohexane, tert-butylcyclohexane and cyclooctane
  • ether solvents such as diisopropyl ether and dibutyl ether
  • fluoroalkyl such as tetrafluoropropanol, octafluoropentanol and hexafluorobutanol
  • alcohol solvents ester solvents such as methyl lactate, ethyl lactate, and methyl isobutyrate. You may use these individually or
  • the substrate of the optical recording medium of the present invention is preferably such that a guide groove formed in a spiral shape is formed on the surface for recording / reproduction with a laser beam.
  • the substrate those that can easily form fine grooves having a narrow track pitch are preferable, and specific examples thereof include glass and plastic.
  • plastics include acrylic resin, methacrylic resin, polycarbonate resin, vinyl chloride resin, vinyl acetate resin, nitrocellulose, polyester resin, polyethylene resin, polypropylene resin, polyimide resin, polystyrene resin, epoxy resin, and alicyclic polyolefin resin.
  • a polycarbonate resin is preferable from the viewpoint of high productivity, cost, moisture absorption resistance, and the like.
  • the substrate is preferably produced by injection molding the plastic.
  • a method for producing a substrate by injection molding include a method using a stamper made of a metal such as Ni in which a guide groove is formed.
  • the master for producing the stamper is produced, for example, as follows. Polish the surface of the disk-shaped glass substrate to be smooth. A photoresist whose thickness is adjusted according to a desired groove depth is applied on the substrate. Next, the photoresist is exposed using a laser beam or an electron beam having a wavelength shorter than that of the blue-violet laser beam and developed, thereby producing a master having a guide groove.
  • a conductive film such as Ni is vacuum-deposited on the surface of the master, and a stamper made of a metal such as Ni in which a guide groove is formed is produced through a plating process.
  • a substrate having guide grooves formed on the surface is produced by injection molding the plastic using this stamper.
  • the guide groove preferably has a height difference (groove depth) between the top surface and the bottom surface of the unevenness of 15 to 80 nm, and more preferably 25 to 50 nm.
  • the ratio of the width of the convex part to the concave part is preferably in the range of 40%: 60% to 60%: 40% (convex part: concave part).
  • the reflective layer is preferably a metal.
  • the metal include gold, silver, aluminum, and alloys thereof. From the viewpoint of reflectivity with respect to laser light having a wavelength of 550 nm or less and surface smoothness, an alloy mainly composed of silver or silver is used. preferable.
  • the silver-based alloy preferably contains about 90% or more of silver, and is selected from the group of Cu, Pd, Ni, Si, Au, Al, Ti, Zn, Zr, Nb, and Mo as components other than silver. Those containing at least one selected from the above are preferred.
  • the reflective layer can be formed on the substrate by, for example, vapor deposition, sputtering (eg, DC sputtering), ion plating, or the like.
  • An intermediate layer may be provided between the reflective layer and the recording layer for the purpose of improving the recording / reproducing characteristics or adjusting the reflectance.
  • Examples of the material for the intermediate layer include metals, metal oxides, metal nitrides, and the like.
  • the thickness of the reflective layer is preferably 5 to 300 nm, and more preferably 30 to 100 nm.
  • the transparent protective layer preferably has no or little absorption with respect to the laser beam used during recording and reproduction, and the real part of the refractive index is relatively large, about 1.5 to 2.0. What has the value of is preferable.
  • the material for the transparent protective layer include metal oxides, metal nitrides, metal sulfides, and mixtures thereof.
  • the thickness of the transparent protective layer is preferably 5 to 50 nm.
  • the thickness of the protective layer is 5 nm or more, a recording signal formed by deforming the recording layer can be clearly separated from an unrecorded portion between the recording marks, so that a better signal can be obtained. Further, when the thickness of the protective layer is 50 nm or less, the transparent protective layer is easily deformed, so that a better signal can be obtained.
  • the transparent protective layer can be formed on the recording layer by sputtering (for example, RF sputtering).
  • the cover layer for example, a polycarbonate sheet having a thickness of about 0.1 mm having an adhesive layer that is transparent to the recording / reproducing laser beam on the surface is used, and the sheet is transparently protected via the adhesive layer. By pressure-bonding to the layer, it can be formed on the transparent protective layer.
  • the adhesive layer is preferably one that does not hinder the deformation of the recording layer and the transparent protective layer during information recording.
  • the cover layer can also be formed using an ultraviolet curable resin, and the ultraviolet curable resin is preferably one that does not hinder the deformation of the recording layer and the transparent protective layer during information recording, like the adhesive layer.
  • the wavelength of the laser beam used for recording is preferably 350 to 530 nm. In general, the shorter the wavelength of laser light used for recording, the higher the density recording possible.
  • laser light examples include, for example, blue-violet laser light having a center wavelength of 405 nm, 410 nm, etc., blue-green high-power semiconductor laser light having a center wavelength of 515 nm, and the center wavelength is 405 nm. Blue-green high-power semiconductor laser light is preferred.
  • SHG may be any piezo element that lacks reflection symmetry, but KDP (KH 2 PO 4 ), ADP (NH 4 H 2 PO 4 ), BNN (Ba 2 NaNb 5 O 15 ), KN ( Preferred examples of SHG include KNbO 3 ), LBO (LiB 3 O 5 ), and compound semiconductors.
  • Specific examples of light (second harmonic) obtained by wavelength conversion by SHG include, for example, 430 nm light obtained by wavelength conversion of semiconductor laser light having a fundamental oscillation wavelength of 860 nm, and semiconductor laser having a fundamental oscillation wavelength of 860 nm. Examples thereof include 430 nm light obtained by wavelength conversion of excitation solid-state laser light.
  • the optical recording medium of the present invention is preferably a BD.
  • the BD is an optical recording medium that uses a blue-violet laser having a wavelength of 405 nm and records a higher density information by reducing the laser spot diameter by setting the NA of the objective lens to 0.85.
  • a reflective layer, a recording layer, a transparent protective layer, and a cover layer thinner than the substrate are sequentially laminated on the substrate. Recording and reproduction is performed by irradiating a blue-violet laser beam from the cover layer side.
  • Example 1 2 1 Complex of Compound (49) and Nickel [Compound (49-N)] 0.50 g of compound (49) and 0.16 g of nickel (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.52 g (yield 97%) of compound (49-N).
  • Example 2 2 1 Complex of Compound (49) and Cobalt [Compound (49-CO)] 0.50 g of compound (49) and 0.16 g of cobalt (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.52 g (yield 97%) of compound (49-CO).
  • Example 3 3 1 Complex of Compound (49) and Aluminum [Compound (49-A)] 0.30 g of compound (49) and 0.093 g of aluminum tris (ethylacetoacetate) were reacted in 3 mL of ethanol at 70 ° C. for 3 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.24 g (yield 79%) of compound (49-A).
  • Example 4 2 1 Complex of Compound (54) and Nickel [Compound (54-N)] 0.20 g of compound (54) and 0.06 g of nickel (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.18 g (yield 86%) of compound (54-N).
  • Example 5 2 1 Complex of Compound (54) and Cobalt [Compound (54-CO)] 0.20 g of compound (54) and 0.06 g of cobalt (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.14 g (yield 64%) of compound (54-CO).
  • Example 6 2 1 Complex of Compound (61) and Nickel [Compound (61-N)] 0.30 g of compound (61) and 0.11 g of nickel (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.35 g (yield 95%) of compound (61-N).
  • Example 7 2 1 Complex of Compound (61) and Cobalt [Compound (61-CO)] 0.30 g of compound (61) and 0.11 g of cobalt (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.35 g of compound (61-CO) (yield 97%).
  • Example 8 2 1 Complex of Compound (63) and Nickel [Compound (63-N)] 0.50 g of compound (63) and 0.15 g of nickel (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.48 g (yield 90%) of compound (63-N).
  • Example 9 2 1 Complex of Compound (63) and Cobalt [Compound (63-CO)] 0.50 g of compound (63) and 0.15 g of cobalt (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.47 g (yield 89%) of compound (63-CO).
  • Example 10 2 1 Complex of Compound (71) and Nickel [Compound (71-N)] 0.20 g of compound (71) and 0.07 g of nickel (II) acetate tetrahydrate were reacted in 3 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.21 g (yield 99%) of compound (71-N).
  • Example 11 2 1 Complex of Compound (71) and Cobalt [Compound (71-CO)] 0.20 g of compound (71) and 0.07 g of cobalt (II) acetate tetrahydrate were reacted in 3 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.21 g (yield 96%) of compound (71-CO).
  • Example 12 2 1 Complex of Compound (77) and Nickel [Compound (77-N)] 0.20 g of compound (77) and 0.06 g of nickel acetate (II) tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.21 g (yield 100%) of compound (77-N).
  • Example 13 2 1 Complex of Compound (77) and Cobalt [Compound (77-CO)] 0.20 g of compound (77) and 0.06 g of cobalt (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.21 g (yield 94%) of compound (77-CO).
  • Example 14 3 1 Complex of Compound (77) and Aluminum [Compound (77-A)] 0.30 g of compound (77) and 0.08 mg of aluminum tris (ethyl acetoacetate) were reacted in 3 mL of ethanol at 70 ° C. for 3 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.30 g (yield 92%) of compound (77-A).
  • Example 15 2 1 Complex of Compound (84) and Nickel [Compound (84-N)] 0.30 g of compound (84) and 0.09 g of nickel (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.31 g (yield 100%) of compound (84-N).
  • Example 16 1 complex of compound (84) and cobalt [compound (84-CO)] 0.30 g of the compound (84) and 0.09 g of cobalt (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.31 g (yield 100%) of compound (84-CO).
  • Example 17 2 1 Complex of Compound (93) and Nickel [Compound (93-N)] 0.15 g of compound (93) and 0.04 g of nickel (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.13 g (yield 83%) of compound (93-N).
  • Example 18 1 complex of compound (93) and cobalt [compound (93-CO)] 0.30 g of compound (93) and 0.08 g of cobalt (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.31 g (yield 100%) of compound (93-CO).
  • Example 19 2 1 Complex of Compound (102) and Nickel [Compound (102-N)] 0.15 g of compound (102) and 0.04 g of nickel (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.16 g (yield 97%) of compound (102-N).
  • Example 20 2 1 Complex of Compound (102) and Cobalt [Compound (102-CO)] 0.30 g of compound (102) and 0.08 g of cobalt (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.33 g (yield 100%) of compound (102-CO).
  • Example 21 1 complex of compound (107) and nickel [compound (107-N)] 0.15 g of the compound (107) and 0.05 g of nickel (II) acetate tetrahydrate were reacted in 5 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.17 g (yield 100%) of compound (107-N).
  • Example 22 1 complex of compound (107) and cobalt [compound (107-CO)] 0.20 g of compound (107) and 0.06 g of cobalt (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.20 g (yield 100%) of compound (107-CO).
  • Example 23 1 complex of compound (112) and nickel [compound (112-N)] 0.20 g of compound (112) and 0.06 g of nickel (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.17 g (yield 79%) of compound (112-N).
  • Example 24 1 complex of compound (112) and cobalt [compound (112-CO)] 0.20 g of compound (112) and 0.06 g of cobalt (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.21 g (yield 98%) of compound (112-CO).
  • Example 25 2 1 Complex of Compound (115) and Nickel [Compound (115-N)] 0.25 g of compound (115) and 0.07 g of nickel acetate (II) tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.24 g (yield 89%) of compound (115-N).
  • Example 26 1 complex of compound (115) and cobalt [compound (115-CO)] 0.25 g of compound (115) and 0.07 g of cobalt (II) acetate tetrahydrate were reacted in 70 mL of ethanol in 5 mL of ethanol for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.25 g of compound (115-CO) (yield 92%).
  • Example 27 2 1 Complex of Compound (120) and Nickel [Compound (120-N)] 0.20 g of compound (120) and 0.05 g of nickel (II) acetate tetrahydrate were reacted in 2 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.21 g of Compound (120-N) (yield 100%).
  • Example 28 1 complex of compound (120) and cobalt [compound (120-CO)] 0.20 g of the compound (120) and 0.05 g of cobalt (II) acetate tetrahydrate were reacted in 2 mL of ethanol at 70 ° C. for 2 hours. After cooling the reaction solution, the precipitated solid was collected by filtration and washed with ethanol to obtain 0.15 g (yield 73%) of compound (120-CO).
  • ⁇ Substrate 101> A polycarbonate resin was injection molded to produce a substrate having a plate thickness of 1.1 mm and a diameter of 12 cm. On the surface of the substrate, a spiral tracking guide groove was formed by wobbling with an amplitude of 20 nm with a period of about 5 ⁇ m as preformat information such as an address signal in accordance with the BD-R disc standard. The guide groove was found to have a track pitch of 0.32 ⁇ m, a groove depth of 42 nm, and a groove width (half-value width at the top and bottom) of 147 nm, as observed and measured with an atomic force microscope.
  • the film thickness of the reflective layer was 45 nm from cross-sectional observation with an electron microscope.
  • ⁇ Recording layer 103> As the dye for forming the recording layer of the optical recording medium, a metal complex of the squarylium compound shown in Table 1 was used.
  • Each of the metal complexes of the squarylium compound described in Table 1 was ultrasonically dissolved in 2,2,3,3-tetrafluoropropanol at about 35 ° C., and a solution having a concentration of 0.5% by weight of the metal complex was obtained.
  • Prepared. About 0.5 g of this solution is dropped on the reflective layer 102 in a spiral shape from the outer periphery to the inner periphery, applied at a rotational speed of 2000 rpm by a spin coating method, and then heated in an oven at 70 ° C. for 30 minutes to form the recording layer 103. Formed.
  • the film thickness of the groove (concave portion) where recording is performed in the recording layer was about 30 nm from cross-sectional observation with an electron microscope.
  • Table 1 shows the results of measuring the absorbance of the dye used in the disk thin film state at 405 nm, which is the wavelength of the blue-violet laser.
  • a transparent protective layer 104 was formed by the method. The film thickness of this recording layer was 17 nm from cross-sectional observation with an electron microscope.
  • ⁇ Cover layer 105> On the transparent protective layer 104, a cover sheet (trade name Opteria, manufactured by Lintec Co., Ltd.) having a thickness of 100 ⁇ m obtained by applying a transparent adhesive to a polycarbonate film sheet is bonded with a sheet roller, and then subjected to pressure defoaming for 15 seconds. Thus, the cover layer 105 was formed.
  • a cover sheet (trade name Opteria, manufactured by Lintec Co., Ltd.) having a thickness of 100 ⁇ m obtained by applying a transparent adhesive to a polycarbonate film sheet is bonded with a sheet roller, and then subjected to pressure defoaming for 15 seconds.
  • the BD-R type optical recording media of Examples 29 to 37 were manufactured using the materials, procedures, and prototype conditions described above.
  • a disk evaluation machine (PDUSTEC ODU-1000) having a pickup head having a wavelength of 405 nm and a numerical aperture NA of 0.85 was used, and a shortest mark of 0.149 ⁇ m at a linear velocity of 4.92 m / sec.
  • a signal of the RLL (1-7) modulation method was modulated with a ternary multi-pulse as shown in FIG. 2, and five tracks were recorded on the groove. Reproduction was performed at a reproduction power of 0.30 mW on the third track at the center of the five recorded tracks.
  • the value obtained by dividing the jitter of the timing difference between the rise and fall of the signal binarized through the limit equalizer and the rise of the clock signal by the window width T (jitter value) was evaluated.
  • the recording conditions of each example were set by optimizing the recording power and multipulse modulation so that the jitter value was minimized.
  • Table 2 the jitter value obtained by recording / reproduction and the peak value of the recording power shown in FIG. 2 are shown as Pwo.
  • the optical recording media obtained in the examples satisfied the BD-R standards (jitter value: 7% or less, Pwo: 6 mW or less). Further, Pwo was as low as 6 mW or less when recording was performed using the optical recording medium obtained in the example so that the jitter value was 7% or less. This indicates that the optical recording medium obtained in the example has high sensitivity photoresponsiveness to blue-violet laser light.
  • an optical recording medium containing a metal complex of a squarylium compound having a highly sensitive photoresponsiveness to blue-violet laser light.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)

Abstract

La présente invention se rapporte à un support d’enregistrement optique utilisant un complexe métallique d’un composé de squarylium qui présente des propriétés de photosensibilité très élevées à la lumière laser bleue-violette. L’invention décrit de manière spécifique un support d’enregistrement optique contenant un complexe métallique d’un composé de squarylium représenté par la formule (I). (Dans la formule, R1 représenté un groupe alkyle éventuellement substitué ou similaire ; R2 représente un groupe alkyle éventuellement substitué ou similaire ; et R3 et R4 peuvent être identiques ou différents et représentent chacun un atome d’hydrogène, un groupe alkyle éventuellement substitué, un groupe NR5R6 (R5 et R6 pouvant être identiques ou différents et représentant chacun un atome d’hydrogène, un groupe hétérocyclique éventuellement substitué ou similaire) ou similaire.)
PCT/JP2009/067508 2008-10-08 2009-10-07 Support d’enregistrement optique contenant un complexe métallique de composé de squarylium Ceased WO2010041691A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011162190A1 (fr) * 2010-06-24 2011-12-29 協和発酵ケミカル株式会社 Complexes métalliques de composés de squarylium et supports d'enregistrement optiques les comprenant

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005059608A1 (fr) * 2003-12-18 2005-06-30 Kyowa Hakko Chemical Co., Ltd. Filtre pour affichage electronique
WO2006011514A1 (fr) * 2004-07-27 2006-02-02 Kyowa Hakko Chemical Co., Ltd. Filtre pour afficheur électronique
WO2006038685A1 (fr) * 2004-10-07 2006-04-13 Kyowa Hakko Chemical Co., Ltd. Filtre pour affichage électronique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005059608A1 (fr) * 2003-12-18 2005-06-30 Kyowa Hakko Chemical Co., Ltd. Filtre pour affichage electronique
WO2006011514A1 (fr) * 2004-07-27 2006-02-02 Kyowa Hakko Chemical Co., Ltd. Filtre pour afficheur électronique
WO2006038685A1 (fr) * 2004-10-07 2006-04-13 Kyowa Hakko Chemical Co., Ltd. Filtre pour affichage électronique

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011162190A1 (fr) * 2010-06-24 2011-12-29 協和発酵ケミカル株式会社 Complexes métalliques de composés de squarylium et supports d'enregistrement optiques les comprenant

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