WO2007125892A1 - 光学記録材料、カルコン型化合物及び金属錯体 - Google Patents
光学記録材料、カルコン型化合物及び金属錯体 Download PDFInfo
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- WO2007125892A1 WO2007125892A1 PCT/JP2007/058801 JP2007058801W WO2007125892A1 WO 2007125892 A1 WO2007125892 A1 WO 2007125892A1 JP 2007058801 W JP2007058801 W JP 2007058801W WO 2007125892 A1 WO2007125892 A1 WO 2007125892A1
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
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- 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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- 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
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Definitions
- the present invention relates to an optical recording material used for an optical recording medium to be recorded by applying information as an information pattern by a laser or the like, and more specifically, it has wavelengths in the ultraviolet and visible regions and is low in energy
- Optical recording material for use in an optical recording medium capable of high-density optical recording and reproduction with a laser etc. a novel chalcon type compound suitable for the optical recording material, and a novel metal using the compound as a ligand It relates to a complex.
- Optical recording media are in widespread use because they have excellent characteristics such as large recording capacity and non-contact recording or reproduction.
- WORM high definition optical disks
- laser ⁇ ⁇ is made to be a minute area of the recording layer, and the characteristics of the optical recording layer are changed and recorded, and the reflection between the recorded part and the unrecorded part Reproduction is performed by the difference in light intensity.
- the wavelength of the semiconductor laser used for recording and reproduction is 750 to 830 nm for CD-R and 620 nm to 690 nm for DVD-R, but further increase in capacity is realized.
- An optical disk using a very short wavelength laser is under study, for example, one using a light of 380 to 420 nm as a recording beam is under consideration!
- Patent Document 1 reports an optical information recording medium containing a metal complex having a chalcone type compound as a ligand
- Patent Document 2 reports an optical recording medium containing a specific chalcone type compound.
- the compounds used for these optical recording media have not been able to match the absorption wavelength characteristics as optical recording materials used for forming an optical recording layer.
- Patent Document 3 reports a light absorbing agent for clothes, and an example of a compound suitably used as the light absorbing agent is an organic dye compound having a chalcone type structure, but By using the organic dye compound having the chalcone structure as an optical recording material It is described and suggested that it can be done.
- Patent Document 1 Japanese Unexamined Patent Application Publication No. 2003-11511
- Patent Document 2 Japanese Patent Application Laid-Open No. 2004-306306
- Patent Document 3 Japanese Patent Application Laid-Open No. 2000-328039
- an object of the present invention is to provide an optical recording material suitable for forming an optical recording layer of an optical recording medium for short wavelength recording light and a novel compound suitable for the optical recording material.
- the present invention has been made based on the above findings, and an object of the present invention is to provide an optical recording material comprising at least one kind of chalcon type compound represented by the following general formula (I). It has been achieved.
- n is 0 or 1
- the ring A and the ring B each independently represent a 5-, 6-, or 6-membered heterocyclic ring, an aromatic ring or a meta-ring structure.
- the aromatic ring may be fused or substituted with another ring.
- the present invention achieves the above object by providing an optical recording material comprising a metal complex using the chalcone type compound represented by the above general formula (I) as a ligand. Further, the present invention achieves the above object by providing an optical recording medium having an optical recording layer formed from the above optical recording material on a substrate. .
- the present invention also provides a fluorocarbon-type compound represented by the following general formula (III) suitable as the above-mentioned optical recording material.
- the present invention also provides a metal complex represented by the following general formula (VI) suitable as the above-mentioned optical recording material.
- the optical recording material of the present invention containing at least one kind of chalcone type compound represented by the above general formula (I), and a metal complex using the above chalcone type compound as a ligand
- the optical recording material of the present invention (hereinafter, the two may be collectively referred to as the optical recording material of the present invention), the optical recording medium of the present invention, the novel chalcone type compound of the present invention and the novel metal complex It will be described in detail based on the form.
- the chalcone type compound according to the present invention and the metal complex having the same as a ligand may contain optical isomers such as enantiomers, diastereomers or racemates, but the optical recording material of the present invention As a matter of course, any of these optical isomers may be isolated and used, or may be used as a mixture thereof. Hereinafter, in the present invention, such optical isomers are not distinguished unless otherwise noted.
- Examples of the five-membered heterocyclic ring represented by ring A and ring B in the above general formula (I) include a pyrrole ring, a birazoridine ring, a pyrazole ring, an imidazole ring, an imidazolidine ring, an oxazole ring and an isoxazole ring.
- a 5- or 6-membered heterocyclic ring represented by ring A and ring B and an aromatic ring may be fused or substituted with another ring, for example, quinoline ring, isoquinoline And rings, indole ring, eurolidine ring, naphthalene ring, anthracene ring, phenanthrene ring, phenylbenzene ring and the like.
- examples of the meta-mouth structure represented by ring B include structures such as, for example, ferrocel, -cke-cenyl, cobalt-sel, and the like.
- a carbo group is bonded to one of the cyclopentadiene rings of meta-futene.
- chalcone type compounds represented by the above general formula (I) those having a structure represented by the following general formula (II) are preferable because they have more appropriate light absorption characteristics as an optical recording material. Yes.
- the ring C represents a benzene ring or a naphthalene ring
- R 16 may be the same or different-O-,- CO-, -OCO- or -COO-, optionally interrupted alkyl group having 1 to 8 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, A meta-cenyl group having 10 to 30 carbon atoms, a halogen atom, a hydroxyl group, a nitro group, a cyano group, or a heterocyclic group having 2 to 30 carbon atoms
- X 1 represents an oxygen atom
- Y 1 represents NH or C—R e (R f )
- R d , R e and R f each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms
- alkyl groups having 1 to 8 carbon atoms, 6 to 6 carbon atoms Each of the 30 aryl group, the aryl group having 7 to 30 carbon atoms, the metallocell group having 10 to 30 carbon atoms and the heterocyclic group having 2 to 30 carbon atoms has a substituent. It may be.
- chalcone type compounds represented by the above general formula (I) compounds having a structure represented by the following general formula ( ⁇ ) are chemically and thermally stable, and the working power is also inexpensive. It is preferable because it can be manufactured.
- ring B 1 is a five or six membered ring
- G represents CH or a nitrogen atom
- J represents an oxygen atom, a sulfur atom, CH or CH.
- one having a structure represented by the following general formula (V) can be easily coordinated with a metal, and further a metal It is useful because it can obtain more appropriate light absorption characteristics as an optical recording material by coordination with
- R 15 may be the same or different
- An alkyl group of 1 to 8 carbon atoms which may be interrupted by one OCO— or one COO, an aryl group of 6 to 30 carbon atoms, a carbon source
- s represents an alkyl group of 1 to 8 carbon atoms which may be interrupted by one OCO— or one COO, an aryl group of 6 to 30
- R 16 in the above general formula (II) is an alkyl group having 1 to 8 carbon atoms which may be interrupted by one O-, one CO-, one OCO-or one COO-, or a C 6-30 carbon atom.
- the Examples of the above-mentioned alkyl group having 1 to 8 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, hexyl, cyclohexyl, Cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, 4-
- Examples of the group include benzyl, phenethyl, 2-phenylpropyl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl and the like, and examples of the above-mentioned meta-octenyl group having 10 to 30 carbon atoms include And heterocyclic groups, and examples of the heterocyclic group having 2 to 30 carbon atoms include pyridyl, pyrimidyl, pyridazyl, piperazil, piperidil, bilair, pyrazolyl, and the like.
- the halogen atom include xylimidazolidine 3yl and 2,4 dihydroxyxazolidine 3-yl, and examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like.
- alkyl group having 1 to 8 carbon atoms aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, metallosel group having 10 to 30 carbon atoms, and carbon Heterocyclic groups having 2 to 30 atoms may also have a substituent, or even a substituent! /, May! Examples of the substituent include the following.
- the total number of carbon atoms in R 16 satisfies the range specified above.
- a substituent for example, methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, cyclopentyl, hexyl, 2- Hexyl, 3 hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2 heptyl, 3 heptyl, isoheptyl, third heptyl, n-octyl, isoocutyl, third Alkyl groups such as octyl, 2-ethylhexyl, noel, isonoel and decyl; methoxy, ethoxy, propoxy, isoproboxy, butoxy, sec-butoxy, tert-butoxy, iso
- Ring group fluorine, chlorine, odor Halogen atoms such as iodine; acetyl, 2-chloroacetyl, propionyl, otatanyl, ataloyl, ataryloyl, methacryloyl, phenylcarbonyl (benzyl), phthaloyl, 4 trifluoromethylbenzoyl, pivaloyl, salicyloyl, salicyloyl, oxaloyl, stearoyl, methoxyl Asyl groups such as carbonyl, ethoxycarbonyl, t-butoxycarpol, n-octadecyloxycarbol, and rubalmoyl; abasic groups such as acetoxyloxy, benzoxyl and the like; aminoamino, aminoamino, dimethylamino, butylamino with butylamino, cyclopentyl Amidated 2-Etyl Hexyl
- X 1 in the above general formula ( ⁇ ) is an oxygen atom, a sulfur atom or a group represented by N—R d
- Y 1 is NH or C—R e (R f )
- R d and R f each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, a carbon atom 7 to 30 aryl, alkyl having 10 to 30 carbon atoms, a cenyl group having 10 to 30 carbon atoms, a halogen atom, a hydroxyl group, a nitro group, a cyano group or a heterocyclic group having 2 to 30 carbon atoms.
- Examples of the methyl aromatic group having 10 to 30 carbon atoms, the heterocyclic group having 2 to 30 carbon atoms, and the halogen atom include the groups exemplified in the explanation of R 16 , and aryl groups having 2 to 8 carbon atoms are mentioned.
- Examples of the alkyl group include vinyl, aryl, crotyl, dimethylaryl, 2-pentel, 2-hexenyl, 2-peptide, 2-o-tatyl and the like.
- the heterocyclic group having 2 to 30 atoms may have a substituent in the same manner as R 16 .
- the substituent include the groups exemplified in the description of R 16 .
- R d and R f have a substituent, the total number of carbon atoms satisfies the range defined above.
- the ring B 1 in the above general formula (IV) is a 5- or 6-membered ring, and these rings may all be carbon atoms or may be a heterocyclic ring. Examples of those composed only of carbon atoms include cyclopentadiene ring and benzene ring, and examples of the five-membered heterocyclic ring include furan ring, thiophen ring, pyrrole ring, pyrazolidine ring, pyrazole ring, imidazole Ring, imidazolidine ring, oxazole ring, isooxazole ring, isooxazolidine ring, thiazole ring, isothiazolidine ring, etc., and examples of the six-membered heterocyclic ring include piperidin ring, piperazine And morpholine ring, thiomorpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring
- R 15 in the above general formula (V) is an alkyl group having 1 to 8 carbon atoms which may be interrupted by O 2, one CO 2, one OCO— or one COO—, or 6 to 30 carbon atoms.
- the heterocyclic group of the formulas 2 to 30 include the groups exemplified in the explanation of R 16 , and any of these groups may have a substituent.
- the substituent include the groups exemplified in the description of R 16 .
- chalcone type compounds represented by the above general formulas (I) to (V) according to the present invention include the following compound Nos. 1 to 42.
- the method for producing the chalcone type compound represented by the above general formula (I) is not particularly limited, and the chalcone type compound can be obtained by a method using a well-known general reaction.
- the production method for example, when n is 0, there is a method of synthesizing by the reaction of a compound having an active methylene group corresponding to the route shown in the following [ ⁇ 9] and the corresponding acid chloride compound. It can be mentioned.
- the ring A and the ring B each independently represent a 5- or 6-membered heterocyclic ring, an aromatic ring or a meta-portal structure.
- the above-mentioned heterocyclic ring and the above-mentioned aromatic ring are the same as other rings and Condensed
- the ring A and the ring B each independently represent a 5- or 6-membered heterocyclic ring, an aromatic ring or a meta-portal structure.
- the above-mentioned heterocyclic ring and the above-mentioned aromatic ring are the same as other rings and It may be condensed or substituted.
- those represented by the above general formula (I) are preferable.
- those represented by the above general formula ( ⁇ ) among those represented by the above general formula ( ⁇ ) more preferably represented by the above general formula ( ⁇ ), those represented by the above general formula (IV)
- those represented by the above-mentioned general formula (IV) which is even more preferable those represented by the above-mentioned general formula (V) are most preferable.
- those represented by the above general formulas (m) to (v) are novel compounds. No. 1 to No. 9, No. 11, No. 13, No. 16 to No. 25, No. 27 to No. 1 described above.
- optical recording material of the present invention comprising a metal complex using the above-mentioned chalcone type compound as a ligand will be described.
- the metal complex is formed by forming a chalcone type compound represented by any one of the above general formulas (I) to (V) as a ligand.
- the metal complex is a metal atom in which at least one coordination portion of the compounds represented by the general formulas (I) to (V) is coordinated to a metal atom, and the metal complex is characterized by the general formulas (I) to (V).
- the oxygen atom in the carbonyl group in the compound represented by and the metal bonding atom of Ring A and Z or Ring B bond to a metal atom to form at least one chelate structure.
- two coordination parts of the ligand may be bonded to another metal.
- a metal complex in which the chalcone-type compound described above is coordinated as an optical recording layer is advantageous in that the light resistance of the optical recording layer is improved. Therefore, as an optical recording material, it is preferable to use a metal complex using the chalcone type compound as a ligand.
- a novel metal complex represented by the following general formula (VI) obtained by coordinating a chalcone type compound represented by the above general formula (V) has an appropriate light absorption property as an optical recording material. More preferred because it is! /.
- ⁇ represents any metal atom selected as a group power which is also a group 2 element, group 8 element, group 9 element, group 10 element, group 11 element, group 12 element and group 13 element power of the periodic table
- ⁇ represents a metal K represents a structure in which k identical ligands are coordinated to each other, and k is 2
- An q represents an q-valent a-on, q represents 1 or 2, and p represents a neutral charge. Represents the factor to keep at. )
- Acid; Octyl phosphate, Dodecyl phosphate, Octadecyl Organic acids such as acid acid, phenyl acid acid, phenol acid acid, 2, 2-methylene bis (4, 6-di-tert-butylphenyl) phosphonic acid Phosphoric acid, bis trifluoromethylsulfonylimidaion, bisperfluorobutanesulfodiimidaion, perfluoro-4-ethlylcyclohexene sulfonate anion, tetrakis (pentafluorophenyl) And the like, and examples of the divalent one include benzenedisulfonic acid ion, naphthalenedisulfonic acid ion and the like.
- the active molecule has a function of de-exciting (tanning) an active molecule in an excited state, and it has an anion group such as a carboxyl group, a phosphonic acid group or a sulfonic acid group in the cyclopentager ring.
- an anion group such as a carboxyl group, a phosphonic acid group or a sulfonic acid group in the cyclopentager ring.
- Meta-tene compounds such as oral sen and rutenocene can also be used if necessary.
- quencher-on examples include those represented by the following general formula (A), (B) or the following formulas (C) and (D); — 43814, JP-A-5-305770, JP-A-6-239028, JP-A-9-309886, JP-A-9-323478, JP-A-10-45767, JP-A-11- 208118, JP-A 2000-168237, JP-A 2002-201373, JP-A 2002- Examples thereof include those described in JP-A-206061, JP-A-2005-297407, JP-B-7-96334, and International Publication WO98Z29257.
- R 9 and R 1Q are each a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, or SO— Represents a G group, G
- R U , R 12 , R 13 and R ′ ′ each independently represent an alkyl group, an alkyl phenyl group, an alkoxy phenyl group or a halogenated phenyl group.
- the metal complex using the chalcone type compound represented by any one of the above general formulas (I) to (V) according to the present invention as a ligand is not particularly limited depending on its production method.
- a method of synthesis by a chelate reaction of a chalcone type compound which is a corresponding ligand and a metal compound there is a method of synthesis by a chelate reaction of a chalcone type compound which is a corresponding ligand and a metal compound.
- Examples of the metal salt complex used in the above-mentioned chelating reaction include inorganic metal salts such as metal halide salts, hydroxides, sulfates and nitrates; metal salts of organic acids such as acetates; methoxy Lower metal alkoxides such as ethoxide, ethoxide and isopropoxide; acetylacetone salt, ED And chelate complexes such as TA salts.
- a basic compound such as sodium hydroxide, lithium hydroxide, sodium methoxide, sodium hydride, sodium amide, lithium amide or an organic amine compound is used as a reaction agent. Good.
- the optical recording material of the present invention contains at least one chalcone-type compound represented by any one of the general formulas (I) to (V), and a metal complex using these as a ligand is It is contained, and it is used as a mixture of these compounds or these compounds and the organic solvent and various compounds which are mentioned later.
- a metal complex using these as a ligand is It is contained, and it is used as a mixture of these compounds or these compounds and the organic solvent and various compounds which are mentioned later.
- lower alcohols such as methanol and ethanol
- ether alcohols such as methyl seport sorb, cetyl sebol, butyl cellosolve and butyl diglycol
- acetone methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol etc Ketones
- acrylates such as ethyl acrylate, butyl acrylate, etc., fluorides such as 2, 2, 3, 3-tetrafluoropropanol, etc.
- Alcohols such as benzene, toluene, xylene, etc .
- Organic solvents such as chlorinated hydrocarbons such as methylene dichloride, dichloroethane, chloroform, etc., the above-mentioned chalcone type compounds or metal complexes, and various kinds described later as required
- Optical recording material in solution by dissolving the compound Create a spin coating the optical recording material on a substrate, spraying, wet coating be applied in Deitsubingu or the like is used. Other methods include vapor deposition and sputtering.
- the amount used is preferably such that the content of the chalcone type compound or the metal complex in the optical recording material of the present invention is 0.1 to 10% by mass.
- the optical recording layer is formed as a thin film, and the thickness thereof is usually 0.000 to LO: z m, and preferably in the range of 0.1 to 5 ⁇ m.
- the chalcone type compound represented by any one of the general formulas (I) to (V) or the metal complex having these as a ligand in the optical recording layer may be used. It is preferable to be formed so as to contain 50 to 50% by weight of L00. Optical recording of such chalcone type compound or metal complex content
- the optical recording material of the present invention is a chalcone type compound represented by V ⁇ of the above general formulas (I) to (V) of the present invention.
- the metal complex is preferably contained in an amount of 50 to 50% by weight based on the solid content of the optical recording material of the present invention.
- the optical recording layer may optionally be a cyanine compound, an azo system, or the like.
- Compounds for use in optical recording layers such as compounds, phthalocyanin compounds, squarylium compounds, etc .; may contain resins such as polyethylene, polyester, polystyrene, polycarbonate etc. surfactants; antistatic agents; lubricants A flame retardant; a radical scavenger such as hindered amine; a pit formation accelerator such as a phenate derivative; a dispersant; an antioxidant; a crosslinking agent; a light resistance imparting agent and the like.
- the recording layer may contain an aromatic nitroso compound, an amine compound, an imimium compound, a bisimmium compound, a transition metal dithiol chelate compound or the like as a quencher such as singlet oxygen.
- the total content of these various compounds in the optical recording layer is preferably in the range of 0 to 50% by mass.
- 0 to 50% by mass is preferable based on the solid content contained in the optical recording material of the present invention U ,.
- the material of the above-mentioned base on which such an optical recording layer is formed is not particularly limited as long as it is substantially transparent to writing (recording) light and reading (reproduction) light.
- glass of polymethinole methacrylate, a resin such as polyethylene terephthalate and polycarbonate, etc. may be used.
- the shape may be any shape such as a tape, a drum, a belt, a disc, etc., depending on the application.
- a reflective film can be formed on the above-mentioned optical recording layer using gold, silver, aluminum, copper or the like by a vapor deposition method or sputtering method, or a dielectric layer is formed on one side by sputtering method.
- a protective layer can be formed on one side or both sides with acrylic resin, ultraviolet curable resin and the like.
- the optical recording material of the present invention is suitable for an optical recording medium using a semiconductor laser for recording and reproduction, and in particular, a high speed recording type CD-R, DVD ⁇ R, HD-DVD-R, BD-R, etc. It is suitable for the known single layer type, double layer type and multilayer type optical disks of the above.
- the novel chalcone type compound of the present invention represented by the above general formula (m) is preferably used as an optical recording material, and also used as an optical filter or the like.
- novel metal complex of the present invention represented by the above general formula (VI) is preferably used as an optical recording material, and also used as an optical filter or the like.
- Production Examples 1 to 10 show production examples of the compounds No. 1 to No. 8, No. 22 and No. 30 which are chalcone type compounds of the present invention, and the following Production Examples 11 to 25 show the compound No.
- the preparation example of compound No. 43-No. 57 which are metal complexes of this invention which makes 1-N o. 6 a ligand is shown.
- Examples 1 to 19 are compounds No. 1 to No. 8 obtained in Production Examples 1 to 8 or the compounds No. 46 to No. 56 obtained in Production Examples 14 to 24 in this present example.
- the preparation of the optical recording material of the invention and the production examples of the optical recording media No. 1 to No. 19 of the invention using the optical recording material will be described.
- Comparative Example 1 is a preparation of a comparative optical recording material using a chalcone type compound having a structure different from the compound of the present invention, and a production example of a comparative optical recording medium No. 1 using the comparative optical recording material.
- the optical recording media Nos. 9 to 11 and 13 obtained in Examples 9 to L 1, 13 and 15 to 19 and The light resistance of the comparative optical recording medium No. 1 obtained in 15 to 19 and Comparative Example 1 was evaluated by measuring the residual rate of absorbance at the maximum absorption wavelength ( ⁇ max) of the UV absorption spectrum. The results are shown in [Table 8].
- the decomposition point is the temperature at which mass loss starts in differential thermal analysis at a temperature rising rate of 10 ° C for Z minutes.
- Recrystallization was performed from 137 g of toluene and drying was performed to obtain crude crystals.
- the crude crystals obtained were covered with 0.20 mol of methyl iodide and 20 g of methanol, The crepe was allowed to react at 100 ° C. for 15 hours. After desolvation, it was recrystallized from a mixed solvent of 6.0 g of ethyl acetate 100 g Z methanol. Drying was performed to obtain crude crystals of the desired product.
- Production Example 8 Compound No. 8 2933, 1708, 161 1, 1583, 1540. 1513, 1463, 1432,
- Production Example 10 Compound No. 30 2919, 1726, 1628, 1532, 15 1 1, 1371. 1328, 1230, 1308. 1384, 1290, 1206, 1 189, 1 130. 1 1080.
- the decomposition point is the mass reduction start temperature of differential thermal analysis at a temperature rising rate of 10 ° C. for Z minutes.
- Production Example 1 1 Compounds No. 43 3026, 1540, 1518, 1462, 1374, 1 157,] 052.
- Production Example 12 Compounds No. 44 3028, 1541, 1518, 1468, 1369, 1247, 1 156, 1055.
- Production Example 13 Compounds No. 45 3036, 1528, 1469, 1435, 1401, 1327, 1267, 1144,
- Each of the chalcone type compounds obtained in the above Preparation Examples 1 to 8 and the metal complex obtained in the above Preparation Examples 14 to 24 is adjusted so that the concentration of the chalcone type compound or the metal complex becomes a concentration of 1.0% by mass.
- the optical recording materials of Examples 1 to 24 were respectively obtained as solutions of 2, 2, 3, 3- tetrafluoropropanol by dissolving in solutions of 3, 3, 3- tetrafluoropropanol.
- the above optical recording material is spin-coated on a polycarbonate disk substrate with a diameter of 12 cm on which a titanium chelate compound (T-50: manufactured by Nippon Soda Co., Ltd.) is applied and hydrolyzed to provide an undercoat layer (0.01 m). To form an optical recording layer with a thickness of 100 nm I got each body.
- a comparative optical recording material is prepared in the same manner as in Examples 1 to 19 except that the following comparative compound No. 1 is used as a chalcone type compound, and a comparative optical recording medium is obtained using the comparative optical recording material.
- the one showing appropriate absorption near the wavelength of the laser light preferably have an absorbance ratio to ⁇ max of 5 to 70%. More preferably, it is 10 to 60%.
- the absorbance ratio is 5%, sufficient sensitivity and modulation degree can not be obtained, and when the absorbance ratio is 70% or more, an appropriate reflectance can not be obtained, and deterioration due to reproduction light occurs. there is a possibility.
- the optical recording material medium having an optical recording layer formed of the optical recording material of the present invention has an absorbance ratio to max of 30 to 60%, and optical recording using a laser beam of 405 nm such as an optical disk for short wavelength laser. It has been confirmed that it is suitable as an optical recording material for media.
- the optical recording material of the present invention has high light fastness and is suitable for forming an optical recording layer of an optical recording medium.
- a chalcone type compound suitable for forming an optical recording layer of an optical recording medium for short wavelength recording light, a metal complex using the compound as a ligand, and a metal complex containing them An optical recording material can be provided.
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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)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Description
Claims
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CN2007800128200A CN101421116B (zh) | 2006-04-28 | 2007-04-24 | 光学记录材料、查耳酮型化合物以及金属络合物 |
KR1020087024420A KR101308638B1 (ko) | 2006-04-28 | 2007-04-24 | 광학기록재료, 캘콘형 화합물 및 금속 착체 |
JP2008513205A JP5102202B2 (ja) | 2006-04-28 | 2007-04-24 | 光学記録材料、カルコン型化合物及び金属錯体 |
US12/296,594 US8277920B2 (en) | 2006-04-28 | 2007-04-24 | Optical recording material, chalcone type compounds and metal complexes |
EP07742236A EP2033798B1 (en) | 2006-04-28 | 2007-04-24 | Optical recording material, chalcone type compounds and metal complexes |
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JP2005297407A (ja) | 2004-04-13 | 2005-10-27 | Toshiba Corp | 追記型情報記録媒体 |
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JP2012232599A (ja) | 2012-11-29 |
US20090269541A1 (en) | 2009-10-29 |
KR20080110784A (ko) | 2008-12-19 |
KR101308638B1 (ko) | 2013-09-23 |
JPWO2007125892A1 (ja) | 2009-09-10 |
US8277920B2 (en) | 2012-10-02 |
JP5591287B2 (ja) | 2014-09-17 |
JP5102202B2 (ja) | 2012-12-19 |
TW200804096A (en) | 2008-01-16 |
EP2033798A4 (en) | 2010-11-17 |
CN101421116A (zh) | 2009-04-29 |
EP2033798B1 (en) | 2012-08-08 |
TWI383896B (zh) | 2013-02-01 |
CN101421116B (zh) | 2011-07-20 |
EP2033798A1 (en) | 2009-03-11 |
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