WO2006035555A1 - Composé cyanine, filtre optique et matériau d’enregistrement optique - Google Patents
Composé cyanine, filtre optique et matériau d’enregistrement optique Download PDFInfo
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- WO2006035555A1 WO2006035555A1 PCT/JP2005/015055 JP2005015055W WO2006035555A1 WO 2006035555 A1 WO2006035555 A1 WO 2006035555A1 JP 2005015055 W JP2005015055 W JP 2005015055W WO 2006035555 A1 WO2006035555 A1 WO 2006035555A1
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- WIPO (PCT)
- Prior art keywords
- general formula
- group
- ring
- carbon atoms
- cyanine compound
- Prior art date
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- -1 Cyanine compound Chemical class 0.000 title claims abstract description 184
- 230000003287 optical effect Effects 0.000 title claims abstract description 105
- 239000000463 material Substances 0.000 title claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000000962 organic group Chemical group 0.000 claims abstract description 8
- 125000001624 naphthyl group Chemical class 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical group [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 108
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
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- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical class [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 10
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical group CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 230000001050 lubricating effect Effects 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
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- 229920000178 Acrylic resin Polymers 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
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- 238000001914 filtration Methods 0.000 description 4
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- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical group CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
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- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 238000005507 spraying Methods 0.000 description 1
- XBRWELTXMQSEIN-UHFFFAOYSA-N squaric acid dibutyl ester Chemical compound CCCCOC1=C(OCCCC)C(=O)C1=O XBRWELTXMQSEIN-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/265—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used for the production of optical filters or electrical components
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
- B41M5/46—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography characterised by the light-to-heat converting means; characterised by the heat or radiation filtering or absorbing means or layers
- B41M5/465—Infrared radiation-absorbing materials, e.g. dyes, metals, silicates, C black
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
- G11B7/2472—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes cyanine
Definitions
- the present invention relates to a novel cyanine compound, an optical filter, and an optical recording material.
- the cyanine compound is useful as an optical recording agent for use in an optical element or the like, particularly an optical recording material using a laser beam or an optical absorbent contained in an optical filter for an image display device.
- Compounds having strong absorption in the range of 500 nm to 700 nm, particularly compounds having a maximum absorption ( ⁇ max) in the range of 550 to 620 nm, are used for recording layers of optical recording media such as DVD-R, liquid crystal display devices ( LCD), plasma display panel (PDP), electoric luminescence display (ELD), cathode ray tube display (CRT), fluorescent display tube, field emission display, etc. Used as an element.
- optical recording media such as DVD-R, liquid crystal display devices (LC), plasma display panel (PDP), electoric luminescence display (ELD), cathode ray tube display (CRT), fluorescent display tube, field emission display, etc.
- Patent Document 1 a cyanine compound containing a meta-orthane linking group is reported.
- the cyanine compound is used particularly in an optical filter, The transmittance in the target wavelength range decreased, and satisfactory performance was not achieved.
- Patent Document 2 reports a cyanine compound having an indole ring and a squarylium structure.
- the cyanine compound has insufficient light resistance, and sustains the function as an optical element. About the power that is not satisfactory.
- Patent Document 1 Japanese Patent Application Laid-Open No. 2003-171571
- Patent Document 2 JP 2004-99713 A
- an object of the present invention is to provide a compound having excellent light resistance, particularly suitable for an optical filter for an image display device and an optical element used for an optical recording material by a laser beam. is there.
- the present invention has been made on the basis of the above findings, and a cyanine compound represented by the following general formula (I), an optical filter containing the cyanine compound, and an optical filter on a substrate
- the present invention provides an optical recording material containing the cyanine compound, which is used for the optical recording layer of an optical recording medium having a recording layer formed thereon.
- ring A 1 represents an optionally substituted benzene ring or naphthenic ring
- B represents a group represented by the following general formula ( ⁇ ) or (III)
- R 1 Represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group having 6 to 30 carbon atoms
- Y 1 represents a hydrogen atom, an organic group having 1 to 30 carbon atoms
- at least one of Y 1 and Y 2 or B 3 in B in the above general formula (I) is represented by the following general formula (IV) Group.
- ring A 2 represents the same group as ring A 1 in general formula (I)
- Y 2 represents the same group as Y 1 in general formula (I).
- X represents an oxygen atom, a sulfur atom, a selenium atom, — CR 2 R 3 —, — NH— or — NY ′ —
- R 2 and R 3 each independently represents an alkyl having 1 to 4 carbon atoms.
- R a to R 1 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the methylene group in the alkyl group may be substituted with 1 O— or —CO—).
- Z is an alkylene group having 1 to 8 carbon atoms which may have a direct bond or a substituent, and the methylene group in the alkylene group is ⁇ 0—, 1 S—, —CO—, —COO—.
- M is Fe, Co , Ni, Ti, Cu, Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, Pt or Ir
- R 5 to R 8 are each independently a hydrogen atom, a halogen atom, an octalogen atom or a carbon atom that may be substituted with an alkyl group having 1 to 4 carbon atoms or a halogen atom. Represents an alkoxy group of 1 to 4 and R 5 and R 6 may combine to form a ring structure.
- Examples of the substituent of the benzene ring or naphthalene ring that may have a substituent represented by A 2 in the general formula (II) and A 3 in the general formula (III) include fluorine, chlorine, bromine, Halogen atoms such as iodine; methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, heptyl, isoheptyl, sec Alkyl groups such as triheptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl; halogen substituents of the alkyl group; methoxy, ethoxy, isopropoxy, propoxy, butoxy, sec-butoxy,
- alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, tert-butylthio; phenyl, naphthyl, 2-methylphenol, 3-methylphenol, 4-methylphenol -Vinyl, 4-vinyl, 3-isopropyl, 4-isopropyl, 4-butyl, 4-isobutyl, 4-tert-butyl, 4-hexyl , 4-cyclohexyl, 4-octyl, 4- (2-ethylhexyl), 4-stearyl, 2, 3 dimethyl, 2, 4 dimethyl, 2,5 dimethyl, 2 , 6 Dimethylphenyl, 3, 4 Dimethylphenyl, 3, 5 Dimethylphenyl Nyl, 2, 4 Ditertiary butylphenyl, 2,5 Ditertiarybutylphenyl, 2,6
- Examples of the alkyl group represented by 1 to 8 carbon atoms represented by R 1 in the general formula (I) and R 4 in the general formula (III) include methyl, ethyl, propyl, isopropyl, , Sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tertamyl, hexyl, cyclohexyl, heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2 —Ethylhexyl and the like, and aryl groups having 6 to 30 carbon atoms represented by R 1 and R 4 include: phenyl, naphthyl, 2-methylphenol, 3-methylenophenyl, 4—Methylphenol, 4-Bulphe, 3-Isopropyl, 4-Isopropyl, 4 But
- Examples of the organic group having 1 to 30 carbon atoms represented by V 1 in the general formula (I), Y 2 in the general formula (II), and Y 3 in the general formula (III) include Methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, cyclohexylmethyl, 2-cyclohexylethyl, heptyl, isohex Butyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl , 2-ethylhexyl, noel, isonoel, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl
- Examples of the alkyl group having 1 to 4 carbon atoms represented by in the general formula (IV) include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl and the like.
- Examples of the group in which the methylene group in the alkyl group is substituted with O include methoxy, ethoxy, propyloxy, isopropyloxy, methoxymethyl, ethoxymethyl, 2-methoxyethyl, etc., and the methylene group in the alkyl group is CO 2.
- substituted group examples include acetyl, 1-carboethyl, acetylmethyl, 1-carbonylpropyl, 2-oxobutyl, 2-acetylethyl, 1-carbonylisopropyl and the like.
- Examples of the alkyl group having 1 to 4 carbon atoms represented by R 2 and R 3 which are groups in X in the general formula (II) include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, Examples of 3- to 10-membered groups formed by linking R 2 and R 3 include cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, 2,4 di Methylcyclobutane 1,1 diyl, 3 dimethylcyclobutane 1,1 diyl, cyclopentane mono 1,1-diyl, cyclohexane mono 1,1-diyl, tetrahydropyran mono-1,4-diyl, thiane-1,4,4-dinore, Piperidine 1,4,4-zinole, N-substituted piperidine 1,4,4-zyl, morpholine-2,2 diyl, morpholine-3,3 diyl,
- the N-substituents include halogen atoms such as fluorine, chlorine, bromine and iodine; methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, Alkyl groups such as hexyl, cyclohexyl, heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl; halogen substituents of the alkyl group; methoxy, ethoxy, Alkoxy groups such as isopropoxy, propoxy, butoxy, sec-butoxy, sec-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy,
- examples of the halogen atom represented by R 5 to include fluorine, chlorine, bromine and iodine, and the number of carbon atoms which may be substituted with a halogen atom is 1 to 4
- the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butanol, isobutynole, chloromethinole, dichloromethinole, trichloromethinole, bromomethinole, dibuomomethyl, tribromomethyl, fluoromethyl, difluoromethyl, and trifluro
- Groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy
- Examples of the ring structure formed by combining R 5 and R 6 include a benzene ring, a naphthalene ring, an anthracene ring, a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, and the like.
- Cyclopentagen ring pyrrole ring, furan ring, thiophene ring, dihydropyrrole ring, pyridine ring, pyran ring, isoxazole ring, pyrazine ring, pyrimidine ring, polydazine ring, pyrazole ring, isothiazole ring, imidazole ring, quinoline ring And rubazole rings, etc., and these rings may be substituted with a halogen atom, an alkyl group, an alkoxy group or the like.
- the method of introducing V 1 in the general formula (I), Y 'and ⁇ 2 in the general formula (II), and ⁇ 3 in the general formula (III) is not particularly limited.
- ⁇ 1 can be introduced by reacting a ⁇ group of 1 ⁇ -indole derivative with a halogenated organic compound such as Hal-Y 1 (Hal: fluorine, chlorine, bromine, iodine).
- Y 'and ⁇ 3 have a molecular weight that increases as the number of carbon atoms increases, and the molar extinction coefficient of the cyanine compound of the present invention represented by the above general formula (I) having these groups may decrease. Therefore, the number of carbon atoms in Y 2 , Y 'and ⁇ 3 is preferably 20 or less, more preferably 10 or less.
- ⁇ in the general formula (I) is a group represented by the general formula (II)
- the ring ⁇ 1 in the general formula (I) is substituted.
- Ben which may have a group A ring that is a zen ring
- ring A 2 in the above general formula (II) has a substituent and is a benzene ring
- X in the above general formula (II) is —CR 2 R 3 — Power It is preferable because it is particularly excellent in terms of cost and light resistance.
- B is particularly preferred when B is a group represented by the above general formula (II), and typical examples include cyanine compounds represented by the following general formula (VI). .
- R 1 R 2 , R 3 , ⁇ 1 and ⁇ 2 represent the same groups as in the above general formula (I) and the above general formula (II), and R and R 2 ′ are independently A halogen atom, a ditro group, a cyano group, an alkyl group having 1 to 8 carbon atoms, a halogen substituent of the alkyl group, an alkoxy group having 1 to 8 carbon atoms, a halogen substituent of the alkoxy group, a carbon atom
- ring A 1 in the above general formula (I) may have a substituent V or a benzene ring; ring A 3 in the above general formula (III) Even if has a substituent, a benzene ring is preferable because it is particularly excellent in cost and light resistance. Accordingly, in the above general formula (I), particularly preferred is the case where B is a group represented by the above general formula (III). As a typical example, a cyanine salt represented by the following general formula (VII) is used. Compound may be mentioned.
- R 1 , R 4 , ⁇ and ⁇ represent the same groups as in the above general formula (I) and the above general formula (III), R 3 , and R 4 ′ are It represents the general formula in (VI) the same group as R! ' ⁇ beauty R 2', p and Q are each independently an integer of 0 to 4, at least one of Y 1 and Y 3, the general formula (IV) is a substituent represented by
- B represents the general formula
- one of Y 1 in the general formula (I) and Y 3 in the general formula (III) is a substituent represented by the general formula (IV). It is particularly preferable because it is excellent in terms of cost and molar extinction coefficient.
- the substituent represented by the above general formula (IV) of the cyanine compound of the present invention may have the number of carbon atoms, although Z in the general formula (IV) may have a substituent. Those having an alkylene group of 1 to 8; those having M force SFe are preferred. Therefore, among the substituents represented by the general formula (IV), the substituent represented by the following general formula (VIII) is particularly preferred.
- R a to R i are the same as those in the general formula (IV), and Z represents an alkylene group having 1 to 8 carbon atoms which may have a substituent.
- Specific examples of the cyanine compound of the present invention include the following compounds Nos. 1 to 126.
- the production method of the cyanine compound of the present invention represented by the above general formula (I) is not particularly limited, and is a force that can be obtained by a method using a well-known general reaction.
- B is a group represented by the above general formula (II)
- compounds and squares that induce a ring structure having a corresponding structure such as the route shown in the following [Chemical Formula 22] It can be synthesized by the reaction of an acid derivative.
- R represents an alkyl group
- D represents C 10. 4 -, PF 6 -, BF 4 one, S b F 6 -, a halogen ⁇ anion or sulfonyl Ruokishianion).
- examples of the halogen represented by D include chlorine, bromine, iodine, etc.
- examples of the sulfo-oxy represented by D include phenol sulfo-loxy, 4- And methylsulfo-loxy, 4-chlorosulfo-loxy and the like.
- the cyanine compound of the present invention is, for example, a route represented by the following [Chemical Formula 23] Can be synthesized.
- the cyanine compound of the present invention described above is suitable as an optical element for light in the range of 500 nm to 700 nm, particularly as an optical element for light in the range of 550 to 620 nm.
- An optical element is an element that performs its function by absorbing specific light.
- Light absorbers, optical recording agents, photosensitizers and the like can be used for an optical recording layer in an optical recording medium such as DVD R, and the light absorbing agent can be a liquid crystal display (LCD), a plasma display panel (PDP), an electoric luminescence display (ELD). ), Cathode ray tube display (CRT), fluorescent display tube, field emission display, and other optical filters for image display devices.
- LCD liquid crystal display
- PDP plasma display panel
- ELD electoric luminescence display
- CTR Cathode ray tube display
- fluorescent display tube field emission display
- field emission display and other optical filters for image display devices.
- the cyanine compound of the present invention has not only excellent optical properties and light stability, but also has a high solubility in an organic solvent. This feature is advantageous for application to optical recording media and optical filters.
- an optical recording layer such as an optical disk is generally formed by applying a solution obtained by dissolving an optical recording agent in an organic solvent by spin coating or spraying. Therefore, it is advantageous that the compound used as the optical recording agent has higher solubility in an organic solvent because the process margin for forming an optical recording layer is increased.
- a compound having a high solubility in an organic solvent has a good compatibility with a synthetic resin, so that it is necessary to uniformly disperse or dissolve the optical element in the synthetic resin. It is also advantageous in the production of optical filters.
- optical filter of the present invention comprising the cyanine compound of the present invention will be described below.
- the optical filter of the present invention containing the cyanine compound of the present invention that absorbs light necessary for image display is small. It is particularly suitable as an optical filter for an image display device used for high quality.
- the optical filter of the present invention can be used not only for image display devices but also for uses such as analysis devices, semiconductor device manufacturing, astronomical observation, and optical communication.
- the optical filter of the present invention When the optical filter of the present invention is used for an image display device, it is usually disposed on the front surface of the display.
- the optical filter of the present invention when the front plate is provided in front of the display that can be directly attached to the surface of the display, the optical filter of the present invention is provided on the front side (outside) or back side (display side) of the front plate. You can paste it.
- the amount of Shianini ⁇ of the invention, per unit area of the optical full Iruta usually 1 ⁇ : LOOOmg / m 2, preferably 5: In LOOmg / m 2 is there.
- the amount is less than LmgZm 2
- the display quality such color filter becomes too strong
- the brightness may be lowered.
- a transparent support may be provided with arbitrary layers such as an undercoat layer, an antireflection layer, a hard coat layer, and a lubricating layer as necessary. It is done.
- the method for adding the optional components such as the cyanine compound of the present invention, the dye compound other than the cyanine compound of the present invention, and various stabilizers to the optical filter of the present invention include, for example, the transparent support or arbitrary layers.
- the cyanine compound of the present invention is suitable for a method of mixing in an adhesive between layers and a method of providing a light absorption layer.
- Examples of the material for the transparent support include inorganic materials such as glass; diacetyl cellulose, triacetinoresenorelose (TAC), propio-noresenorelose, butyrinoresenorelose, acetinolepropio-noresenorelose Polyester; Polycarbonate; Polyethylene; Polyethylene terephthalate, Polyethylene naphthalate, Polybutylene terephthalate, Poly 1,4-cyclohexanedimethylene terephthalate, Polyethylene 1, 2 Diphenoxetane 4, 4 Polyesters such as' -dicarboxylate and polybutylene terephthalate; Polystyrene; Polyolefins such as polyethylene, polypropylene and polymethylpentene; Acrylic resins such as polymethylmethacrylate; Polysulfone; Poly Terusuruhon; polyether ketone; polyetherimides; polyoxyethylene, and polymer materials such as nor-bornene ⁇ is.
- TAC
- An infrared absorber, an ultraviolet absorber, inorganic fine particles, and the like can be added to these transparent supports, and various surface treatments can be applied to the transparent support.
- Examples of the inorganic fine particles include silicon dioxide, titanium dioxide, barium sulfate, and charcoal. Acid calcium, talc, kaolin and the like can be mentioned.
- Examples of the various surface treatments include chemical treatment, mechanical treatment, corona discharge treatment, flame treatment, ultraviolet irradiation treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment, mixed acid treatment. And ozone oxidation treatment.
- the undercoat layer is a layer used between the transparent support and the light absorption layer when a light absorption layer containing a light absorber is provided.
- the undercoat layer is a layer containing a polymer having a glass transition temperature of ⁇ 60 to 60 ° C., a layer having a rough surface on the light absorption layer side, or a layer containing a polymer having an affinity for the polymer of the light absorption layer.
- the undercoat layer is provided on the surface of the transparent support on which the light absorption layer is not provided, and the adhesive strength between the transparent support and the layer provided thereon (for example, an antireflection layer or a hard coat layer).
- the thickness of the undercoat layer is 2 ⁇ ! ⁇ 20 m is preferred 5 nm ⁇ 5 ⁇ m is more preferred 20 nm ⁇ 2 ⁇ m is more preferred 50 nm ⁇ l ⁇ m is still more preferred 80 ⁇ ! Most preferred is ⁇ 300 nm.
- the undercoat layer containing a polymer having a glass transition temperature of ⁇ 60 to 60 ° C. adheres the transparent support and the filter layer due to the tackiness of the polymer. Polymers having a glass transition temperature of ⁇ 60 to 60 ° C.
- the glass transition temperature is preferably 50 ° C or lower, more preferably 40 ° C or lower, more preferably 30 ° C or lower, and even more preferably 25 ° C or lower. Further, it is most preferably 20 ° C or less.
- the elastic modulus at 25 ° C of the undercoat layer is preferably 1 to 1000 MPa, more preferably 5 to 800 MPa, and even more preferably 10 to 500 MPa.
- the undercoat layer having a rough surface on the light absorption layer side forms a light absorption layer on the rough surface, thereby bonding the transparent support and the light absorption layer.
- the undercoat layer having a rough surface on the light absorption layer side can be easily formed by applying a polymer latex.
- the average particle size of the latex is preferably 0.02 to 3 / ⁇ ⁇ , and more preferably 0.05 to 1 / ⁇ ⁇ .
- polymers having an affinity for the binder polymer of the light absorption layer include acrylic resin, cellulose derivatives, and gelatin. , Casein, starch, polybulal alcohol, soluble nylon, and polymer latex.
- two or more undercoat layers may be provided.
- a solvent for swelling the transparent support, a matting agent, a surfactant, an antistatic agent, a coating aid, a hardening agent and the like may be added.
- a low refractive index layer is essential.
- the refractive index of the low refractive index layer is lower than the refractive index of the transparent support.
- the refractive index of the low refractive index layer is preferably 1.20 to L55, more preferably 1.30 to L50.
- the thickness of the low refractive index layer is preferably 50 to 400 nm, more preferably 50 to 200 nm.
- the low refractive index layer is a layer made of a fluorine-containing polymer having a low refractive index (Japanese Patent Laid-Open No. 57-34526, Japanese Patent Laid-Open No. 3-130103, Japanese Patent Laid-Open No.
- the layer containing fine particles voids can be formed in the low refractive index layer as microvoids between or within the fine particles.
- the layer containing fine particles preferably has a porosity of 3 to 50% by volume, and more preferably has a porosity of 5 to 35% by volume.
- a layer having a high refractive index (medium'high refractive index layer) is laminated in addition to the low refractive index layer in the antireflection layer.
- the refractive index of the high refractive index layer is preferably 1.65-2.40, more preferably 1.70-2.20.
- the refractive index of the middle refractive index layer is adjusted to be an intermediate value between the refractive index of the low refractive index layer and the refractive index of the high refractive index layer.
- the refractive index of the middle refractive index layer is preferably 1.50 to L90, more preferably 1.55 to L70.
- the thickness of the medium / high refractive index layer is preferably 5 ⁇ to 100 / ⁇ ⁇ , more preferably 10 ⁇ to 10 / ⁇ m, and most preferably 30 ⁇ to 1 / ⁇ ⁇ . preferable.
- the haze of the medium / high refractive index layer is preferably 5% or less, more preferably 3% or less, and even more preferably 1% or less.
- the middle / high refractive index layer can be formed using a polymer binder having a relatively high refractive index.
- Polymers with a high refractive index include polystyrene and styrene copolymer Body, polycarbonate, melamine resin, phenol resin, epoxy resin, polyurethane obtained by reaction of cyclic (alicyclic or aromatic) isocyanate and polyol.
- Polymers having other cyclic (aromatic, heterocyclic, and alicyclic) groups and polymers having a non-fluorine atom or a rogen atom as a substituent also have a high refractive index. You may use the polymer formed by the polymerization reaction of the monomer which introduce
- inorganic fine particles may be dispersed in the polymer binder.
- the refractive index of the inorganic fine particles is preferably 1.80 to 2.80.
- the inorganic fine particles are preferably formed from a metal oxide or sulfide.
- metal oxides or sulfates include titanium oxide (for example, rutile, mixed crystals of rutile Z anatase, anatase, amorphous structure), tin oxide, indium oxide, zinc oxide, zirconium oxide, sulfur oxide. Examples include lead oxide. Among these, titanium oxide, tin oxide, and indium oxide are particularly preferable.
- the inorganic fine particles are mainly composed of oxides or sulfides of these metals, and can further contain other elements.
- the main component means a highest content (Weight 0/0) among the components constituting the particles.
- Other elements include Ti, Zr, Sn, Sb, Cu, Fe, Mn, Pb, Cd, As, Cr, Hg, Zn, Al, Mg, Si, P, and S.
- the surface of the antireflection layer can be provided with an antiglare function (function of scattering incident light on the surface and preventing the scenery around the film from moving to the film surface).
- an antiglare function function of scattering incident light on the surface and preventing the scenery around the film from moving to the film surface.
- An antireflection layer having an antiglare function can be obtained.
- An antireflection layer having an antiglare function generally has a haze of 3 to 30%.
- the hard coat layer has a height higher than the hardness of the transparent support.
- the hard coat layer preferably contains a crosslinked polymer.
- the hard coat layer can be an acrylic, urethane or epoxy polymer, oligomer or monomer (eg UV curable) It can be formed using (resin). Silica-based material strength can also be achieved by forming a hard coat layer.
- a lubricating layer may be formed on the surface of the antireflection layer (low refractive index layer).
- the lubricating layer has a function of imparting slipperiness to the surface of the low refractive index layer and improving scratch resistance.
- the lubricating layer can be formed using polyorganosiloxane (for example, silicon oil), natural wax, petroleum wax, higher fatty acid metal salt, fluorine-based lubricant or derivative thereof.
- the thickness of the lubricating layer is preferably 2 to 20 nm.
- the cyanine compound of the present invention can be used as it is, and a binder can also be used.
- the noda include natural polymer materials such as gelatin, casein, starch, cellulose derivatives, and alginic acid, or polymethylmetatalylate, polybutybutyral, polybutylpyrrolidone, polybutyl alcohol, polychlorinated bur, Synthetic polymer materials such as styrene butadiene copolymer, polystyrene, polycarbonate and polyamide are used.
- the undercoat layer, the antireflection layer, the hard coat layer, the lubricating layer, the light absorbing layer, and the like can be formed by a general coating method.
- Application methods include dip coating, air knife coating, curtain coating, roller coating, wire bar coating, gravure coating, and etatrusion coating using a hopper (described in US Pat. No. 2681294).
- Etc. Two or more layers may be formed by simultaneous application.
- the simultaneous application method for example, U.S. Pat. No. 2761791, U.S. Pat.No. 2941898, U.S. Pat.No. 3508947, U.S. Pat.No. 3526528, and Yuji Harasaki “Coating Engineering”, page 253 (1973, Published by Asakura Shoten).
- optical recording material of the present invention comprising the cyanine compound of the present invention used for the optical recording layer of an optical recording medium having an optical recording layer formed on a substrate is described below. This is explained below.
- the cyanine compound of the present invention represented by the general formula (I) is used as an optical recording material used for an optical recording layer in an optical recording medium for recording information by applying information as a thermal information pattern by a laser or the like. Is also useful, and is particularly suitable for an optical recording material used for an optical recording layer of an optical recording medium such as DVD-R or DVD + R.
- the light of the present invention The chemical recording material is a material used for forming the optical recording layer, and the present invention represented by the above general formula (I) and the above-mentioned general formula (I). It is a mixture of an organic solvent and various organic compounds described later.
- a method for forming the optical recording layer of the optical recording medium generally, lower alcohols such as methanol and ethanol; ether alcohols such as methyl caffeosolve, ethylcethylsolve solve, butylcectosolve solvent, and butyldiglycol are used.
- lower alcohols such as methanol and ethanol
- ether alcohols such as methyl caffeosolve, ethylcethylsolve solve, butylcectosolve solvent, and butyldiglycol are used.
- Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and diacetone alcohol, esters such as ethyl acetate, butyl acetate and methoxyethyl acetate; acrylics such as ethyl acrylate and butyl acrylate Acid esters, fluorinated alcohols such as 2, 2, 3, 3-tetrafluoropropanol; hydrocarbons such as benzene, toluene, xylene; chlorination of methylene dichloride, dichloroethane, chloroform, etc.
- the cyanine compound and various compounds of the present invention are dissolved in an organic solvent such as hydrocarbons.
- the solution on the substrate, spin coating, spray one, wet coating is applied by Deitsubingu etc., evaporation, and sputtering method, etc.
- the thickness of the optical recording layer is usually from 0.001 to 10 ⁇ m, preferably from 0.01 to 5 ⁇ m.
- the content of the cyanine compound of the present invention in the optical recording material of the present invention is preferably 10 to L00 wt% in the solid content contained in the optical recording material of the present invention.
- the optical recording material of the present invention includes other cyanine compounds, azo compounds, phthalocyanine compounds, oxonol compounds, squarylium compounds, and styryl compounds as necessary.
- quencher such as singlet oxygen. Quencher-on may be used.
- these various compounds are used in the solid content contained in the optical recording material of the present invention, preferably in an amount ranging from 0 to 50% by weight.
- a reflective film can be formed by vapor deposition or sputtering using gold, silver, aluminum, copper, or the like, acrylic resin, ultraviolet curable resin, or the like.
- a protective layer can also be formed with fat or the like.
- the present invention will be described in more detail with reference to production examples, examples, comparative examples, and evaluation examples.
- the present invention is not limited by the following examples.
- the following production examples 1 and 2 show examples of the cyanine compounds of the present invention.
- evaluation examples 1 and 2 the cyanine compounds of the present invention and the comparative compounds obtained in the production examples 1 and 2 are shown.
- the solubility and light resistance were evaluated.
- the following Examples 1 to 6 show one example of the optical filter of the present invention using the cyanine compound of the present invention obtained in Production Examples 1 and 2, and the following Comparative Examples 1 to 3 are comparative examples.
- An example of an optical filter using a compound is shown.
- Examples 7 and 8 below show examples of the optical recording material of the present invention.
- N-isoamyl-1,2,3,3 trimethyl 3H-indolium iodine salt 10.6g (0.O3mol), triethylamine 4.5g (0.045mol) and ethanol 45g into a nitrogen-substituted reaction flask, and homogenize at room temperature. Until stirred. 8.0 g (0. 3 mol) of succinic acid dibutyl ester was added dropwise, and the mixture was further stirred at room temperature for 5 hours. The solid was filtered off and washed with methanol to obtain 7.2 g (yield: 64%) of the target product, Intermediate 2, as yellow crystals.
- UV absorption measurement black mouth form solvent
- the cyanine compound of the present invention has excellent light resistance.
- the shear strength, especially the cyanine compound of the present invention having the group represented by the general formula (II) is also excellent in solubility, as shown in Table 1.
- composition was melt-kneaded for 5 minutes at 260 ° C with a plast mill. After kneading, a dye-containing pellet was obtained with a nozzle force extrusion water cooled pelletizer having a diameter of 6 mm. This pellet was formed into a thin plate having a thickness of 0.25 mm at 250 ° C. using an electric press. When this thin plate was measured with a spectrophotometer U-3010 manufactured by Hitachi, Ltd., max was 589 nm and the half width was It was 28 nm.
- a thin plate was molded and measured by the same method as in Example 1 except that Compound No. 10 was used instead of Compound No. 1, and ⁇ max was 582 nm and the half-value width was 3 ⁇ 42 nm.
- a thin plate was molded and measured by the same method as in Example 1 except that Comparative Compound No. 3 shown below in [Chemical Formula 25] was used instead of Compound No. 1, and ⁇ max was The half width at 596 nm was 64 nm.
- a UV varnish was prepared according to the following composition, and the UV varnish was applied to a 188 micron thick polyethylene terephthalate film subjected to easy adhesion treatment with a bar coater # 9 and then dried at 80 ° C. for 30 seconds. After that, ultraviolet rays were irradiated with lOOmJ with a high-pressure mercury lamp with an infrared cut film filter to obtain a film with a cured film thickness of about 5 microns. When this was measured with Hitachi Ltd. Spectrophotometer U-3010, max was 590nm and half-width was 28. nm.
- a film was prepared and measured in the same manner as in Example 3 except that Compound No. 10 was used instead of Compound No. 1, and max was 583 nm and the half-width was 31 nm.
- a film was prepared and measured in the same manner as in Example 3 except that Comparative Compound No. 3 was used instead of Compound No. 1, and ⁇ max was 596 nm and the half-value width was 65 nm. It was hot.
- a binder composition with the following composition, apply the binder composition to 188 micron thick polyethylene terephthalate (PET) film with easy adhesion treatment with Barcotater # 9 and dry at 80 ° C for 30 seconds I let you. Thereafter, this film was thermocompression bonded to a 0.9 mm-thick alkali glass plate at 100 ° C. to prepare a PET protective glass plate containing a light-absorbing dye in the binder layer between the glass plate and the PET film. About this, when it was measured with Hitachi, Ltd. Spectrophotometer U-3010, the maximum was 590 nm and the half width was 28 nm.
- PTT polyethylene terephthalate
- a PET protective glass plate was prepared and measured by the same method as in Example 5 except that Compound No. 10 was used instead of Compound No. 1, and ⁇ max was 582 nm and the half width was 32 nm. Met.
- a PET protective glass plate was prepared in the same manner as in Example 5 except that Comparative Compound No. 3 was used instead of Compound No. 1, and ⁇ max was 596 nm and the half-value width was It was 64 nm.
- the optical filters 1 of Comparative Examples 1 to 3 have absorption at a specific wavelength (550 to 620 nm), they may absorb even necessary light having a large half-value width.
- the optical filters of Examples 1 to 6 using the cyanine compound of the present invention have sharp absorption (half-value width of 50 nm or less) at a specific wavelength (550 to 620 nm), It is clear that the performance as an optical filter is excellent.
- a test piece was prepared in the same manner as in Evaluation Example 2 using Compound No. 1. With respect to this specimen, the absorption UV spectrum of the thin film and the UV spectrum of the reflected light at an incident angle of 5 ° were measured. As a result, the absorption max was 613 nm and the reflected light max was 650 nm.
- a test piece was prepared in the same manner as in Evaluation Example 2 using Compound No. 10. With respect to this test piece, the absorption UV spectrum of the thin film and the UV spectrum of the reflected light at an incident angle of 5 ° were measured. As a result, the absorption max was 612 nm and the reflected light max was 648 nm.
- the optical recording medium it is more preferable that the absorption intensity of the reflected light is higher in the vicinity of the wavelength of the laser light to be used. From the results of Examples 7 and 8, it is clear that the cyanine compound of the present invention is suitable for an optical recording material used for an optical recording medium using a 650 nm laser beam such as DVD-R.
- a novel cyanine compound that is excellent in light resistance and solubility and suitable as an optical element can be provided.
- An optical filter using the cyanine compound is suitable as an optical filter for image display, and an optical recording material containing the cyanine compound is used to form an optical recording layer of an optical recording medium. It is suitable for.
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Optical Filters (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Abstract
Priority Applications (3)
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CN2005800249973A CN1989208B (zh) | 2004-09-28 | 2005-08-18 | 花青化合物、滤光器和光学记录材料 |
KR1020077001726A KR101226194B1 (ko) | 2004-09-28 | 2005-08-18 | 시아닌화합물, 광학 필터 및 광학 기록재료 |
JP2006537646A JP4979384B2 (ja) | 2004-09-28 | 2005-08-18 | シアニン化合物、光学フィルター及び光学記録材料 |
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PCT/JP2005/015055 WO2006035555A1 (fr) | 2004-09-28 | 2005-08-18 | Composé cyanine, filtre optique et matériau d’enregistrement optique |
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JP (1) | JP4979384B2 (fr) |
KR (1) | KR101226194B1 (fr) |
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WO (1) | WO2006035555A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006109618A1 (fr) * | 2005-04-05 | 2006-10-19 | Adeka Corporation | Composés cyanines, filtres optiques et supports d'enregistrement optique |
WO2012029520A1 (fr) | 2010-09-03 | 2012-03-08 | 株式会社Adeka | Filtre de conversion en couleur |
WO2019167930A1 (fr) * | 2018-02-28 | 2019-09-06 | 富士フイルム株式会社 | Composition de résine, filtre optique, dispositif d'affichage d'image, élément d'imagerie à semi-conducteurs et composé |
JP2021170125A (ja) * | 2017-09-29 | 2021-10-28 | 富士フイルム株式会社 | 偏光板保護膜、偏光板、及び液晶表示装置 |
Families Citing this family (2)
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CN101709150A (zh) * | 2009-08-14 | 2010-05-19 | 上海拓引数码技术有限公司 | 一种花菁类光记录媒体染料 |
JP6305331B2 (ja) * | 2012-04-25 | 2018-04-04 | 株式会社Adeka | 波長カットフィルタ |
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US4743530A (en) * | 1986-11-21 | 1988-05-10 | Eastman Kodak Company | Negative working photoresists responsive to longer wavelengths and novel coated articles |
US4743531A (en) * | 1986-11-21 | 1988-05-10 | Eastman Kodak Company | Dye sensitized photographic imaging system |
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- 2005-08-18 KR KR1020077001726A patent/KR101226194B1/ko not_active IP Right Cessation
- 2005-08-18 WO PCT/JP2005/015055 patent/WO2006035555A1/fr active Application Filing
- 2005-08-18 JP JP2006537646A patent/JP4979384B2/ja not_active Expired - Fee Related
- 2005-08-18 CN CN2005800249973A patent/CN1989208B/zh not_active Expired - Fee Related
- 2005-08-29 TW TW094129542A patent/TW200624513A/zh not_active IP Right Cessation
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JP2002228829A (ja) * | 2001-02-02 | 2002-08-14 | Asahi Denka Kogyo Kk | 光学フィルター |
JP2002225434A (ja) * | 2001-02-02 | 2002-08-14 | Asahi Denka Kogyo Kk | 光学記録材料 |
JP2002294094A (ja) * | 2001-04-03 | 2002-10-09 | Hayashibara Biochem Lab Inc | シアニン色素 |
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006109618A1 (fr) * | 2005-04-05 | 2006-10-19 | Adeka Corporation | Composés cyanines, filtres optiques et supports d'enregistrement optique |
US7745632B2 (en) | 2005-04-05 | 2010-06-29 | Adeka Corporation | Cyanine compounds, optical filters, and optical recording materials |
US8193366B2 (en) | 2005-04-05 | 2012-06-05 | Adeka Corporation | Cyanine compounds |
WO2012029520A1 (fr) | 2010-09-03 | 2012-03-08 | 株式会社Adeka | Filtre de conversion en couleur |
US9110350B2 (en) | 2010-09-03 | 2015-08-18 | Adeka Corporation | Color conversion filter |
JP2021170125A (ja) * | 2017-09-29 | 2021-10-28 | 富士フイルム株式会社 | 偏光板保護膜、偏光板、及び液晶表示装置 |
JP7162103B2 (ja) | 2017-09-29 | 2022-10-27 | 富士フイルム株式会社 | 偏光板保護膜、偏光板、及び液晶表示装置 |
US11733435B2 (en) | 2017-09-29 | 2023-08-22 | Fujifilm Corporation | Polarizing plate protective film, polarizing plate, and liquid crystal display device |
WO2019167930A1 (fr) * | 2018-02-28 | 2019-09-06 | 富士フイルム株式会社 | Composition de résine, filtre optique, dispositif d'affichage d'image, élément d'imagerie à semi-conducteurs et composé |
JPWO2019167930A1 (ja) * | 2018-02-28 | 2020-12-17 | 富士フイルム株式会社 | 樹脂組成物、光学フィルター、画像表示装置、固体撮像素子、及び化合物 |
US12049556B2 (en) | 2018-02-28 | 2024-07-30 | Fujifilm Corporation | Resin composition, optical filter, image display device, solid-state imaging element, and compound |
Also Published As
Publication number | Publication date |
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TW200624513A (en) | 2006-07-16 |
JP4979384B2 (ja) | 2012-07-18 |
CN1989208B (zh) | 2011-12-14 |
JPWO2006035555A1 (ja) | 2008-05-15 |
CN1989208A (zh) | 2007-06-27 |
KR20070057135A (ko) | 2007-06-04 |
TWI371471B (fr) | 2012-09-01 |
KR101226194B1 (ko) | 2013-01-24 |
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