JP4979384B2 - シアニン化合物、光学フィルター及び光学記録材料 - Google Patents
シアニン化合物、光学フィルター及び光学記録材料 Download PDFInfo
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- JP4979384B2 JP4979384B2 JP2006537646A JP2006537646A JP4979384B2 JP 4979384 B2 JP4979384 B2 JP 4979384B2 JP 2006537646 A JP2006537646 A JP 2006537646A JP 2006537646 A JP2006537646 A JP 2006537646A JP 4979384 B2 JP4979384 B2 JP 4979384B2
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- cyanine compound
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- -1 Cyanine compound Chemical class 0.000 title claims description 213
- 230000003287 optical effect Effects 0.000 title claims description 99
- 239000000463 material Substances 0.000 title claims description 22
- 239000000758 substrate Substances 0.000 claims description 4
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 1
- 239000010410 layer Substances 0.000 description 108
- 150000001875 compounds Chemical class 0.000 description 62
- 238000000034 method Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- 230000031700 light absorption Effects 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
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- 239000000047 product Substances 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-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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- 239000003795 chemical substances by application Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 238000000576 coating method Methods 0.000 description 6
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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 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
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- 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
- 229910052801 chlorine Inorganic materials 0.000 description 5
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 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 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 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 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 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
- 125000003118 aryl group Chemical group 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
- 238000000354 decomposition reaction Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 150000002367 halogens Chemical group 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
- 238000005259 measurement Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- 125000005504 styryl group Chemical group 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
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- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 3
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
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- 125000000962 organic group Chemical group 0.000 description 3
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- XBRWELTXMQSEIN-UHFFFAOYSA-N squaric acid dibutyl ester Chemical compound CCCCOC1=C(OCCCC)C(=O)C1=O XBRWELTXMQSEIN-UHFFFAOYSA-N 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
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- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
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- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
Landscapes
- 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)
Description
本発明のシアニン化合物は、吸収の半値幅が小さいので、画像表示に必要な光の吸収が小さく、本発明のシアニン化合物を含有する本発明の光学フィルターは、表示画像の高品質化に用いられる画像表示装置用の光学フィルターとして特に好適なものである。尚、本発明の光学フィルターは、画像表示装置用以外に、分析装置用、半導体装置製造用、天文観測用、光通信用等の用途にも用いることができる。
前記一般式(I)で表される本発明のシアニン化合物は、情報をレーザ等による熱的情報パターンとして付与することにより記録する光学記録媒体における光学記録層に使用される光学記録材料にも有用であり、特にDVD−R、DVD+R等の光学記録媒体の光学記録層に使用される光学記録材料に好適である。なお、本発明の光学記録材料は、光学記録層を形成するために用いられる材料であり、前記一般式(I)で表される本発明のシアニン化合物、及び前記一般式(I)で表される本発明のシアニン化合物と後述する有機溶媒や各種化合物との混合物のことである。
下記製造例1及び2は、本発明のシアニン化合物の実施例を示し、下記評価例1及び2ににおいては、製造例1及び2で得られた本発明のシアニン化合物並びに比較化合物について、溶解性及び耐光性の評価を行った。また、下記実施例1〜6は、製造例1及び2で得られた本発明のシアニン化合物を用いた本発明の光学フィルターの実施例を示し、下記比較例1〜3は、比較化合物を用いた光学フィルターの実施例を示す。また、下記実施例7及び8は、本発明の光学記録材料の実施例を示す。
<ステップ1>中間体1の合成
窒素置換した反応フラスコに、インドール0.7g(6mmol)、水酸化カリウム0.5g(9mmol)、テトラブチルアンモニウムブロミド0.08g(0.24mmol)及びテトラヒドロフラン4gを仕込み、60℃で1時間攪拌した。フェロセンブタノールトシルエステル2.5g(6mmol)を加え、60℃でさらに3時間攪拌した。室温に冷却し、キシレン75mlを加えて水層が中性になるまで水洗を行った。硫酸ナトリウムによる脱水、脱溶媒を行い、黄色透明オイルとして目的物である中間体1の2.1g(粗収率96%)を得た。
窒素置換した反応フラスコに、N−イソアミル−2,3,3−トリメチル−3H−インドリウムヨウ素塩10.6g(0.03mol)、トリエチルアミン4.5g(0.045mol)及びエタノール45gを仕込み、室温で均一になるまで攪拌した。スクエア酸ジブチルエステル8.0g(0.03mol)を滴下し、室温でさらに5時間攪拌した。固体をろ別し、メタノールで洗浄して黄色結晶として目的物である中間体2の7.2g(収率64%)を得た。
窒素置換した反応フラスコに、ステップ2で得られた中間体2の7.0g(0.018mol)、酢酸60g及び水30gを仕込み、100℃で5時間加熱還流した。室温に冷却後、反応液を減圧下で濃縮乾固し、残渣を酢酸エチルで洗浄し、析出した固体をろ別して、緑色結晶として目的物である中間体3の4.2g(収率70%)を得た。
窒素置換した反応フラスコにステップ1で得られた中間体1の2.1g(6mmol)、ステップ3で得られた中間体3の1.9g(6mmol)、ブタノール11.9g及びトルエン11.9gを仕込み、生成する水を除去しながら100℃で7時間加熱還流した。室温に冷却後、溶媒を留去し、カラム精製(シリカゲル、酢酸エチル:n−ヘキサン=1:1)を行い、次いで、トルエンから再結晶を行い、紫色結晶を1.0g(収率26%、HPLC純度99%)得た。得られた紫色結晶は、目的物である化合物No.1であることが確認された。得られた紫色結晶についての分析結果を以下に示す。
(1)1H−NMR(CDCl3溶媒)
(ピークトップのケミカルシフトppm;多重度;プロトン数)(1.08;d;6)、(1.55;q;2)、(1.73;m;2)、(1.82;m;1)、(1.86;s;6)、(1.94;m;2)、(2.37;t;2)、(4.02;t+t;4)、(4.06;s;5)、(4.12;d;2)、(4.18;t;2)、(6.17;s;1)、(7.11;d;1)、(7.27;d;1)、(7.30;d;1)、(7.32;t;1)、(7.38;t;1)、(7.39;t;1)、(7.45;d;1)、(8.40;s;1)、(8.84;t;1)
(2)IR吸収(cm-1)2960、1602、1572、1483、1458、1388、1311、1292、1199、1143、1093
(3)UV吸収測定(クロロホルム溶媒)
濃度:3.5×10-6mol/l
λmax;590nm、ε;1.93×105
(4)分解温度(TG−DTA:窒素気流(100ml/分)中、昇温速度10℃/分)
270℃;ピークトップ
<ステップ1>中間体4の合成
窒素置換した反応フラスコに、2−メチルインドール0.66g(5mmol)、水酸化カリウム0.42g(7.5mmol)、テトラブチルアンモニウムブロミド0.06g(0.2mmol)、テトラヒドロフラン9.3g及びフェロセンブタノールトシルエステル2.1g(5mmol)を仕込み、90℃で8時間攪拌した。室温に冷却し、トルエン80mlを加えて水層が中性になるまで水洗を行った。硫酸ナトリウムによる脱水、脱溶媒を行い、褐色透明オイルとして目的物である中間体4の1.8g(粗収率95%)を得た。
窒素置換した反応フラスコにステップ1で得られた中間体4の1.8g(4.8mmol)、ブタノール5.9g、トルエン3.0g及びスクエア酸ジブチルエステル0.27g(2.4mmol)を仕込み、生成する水を除去しながら120℃で4時間加熱還流した。室温に冷却後、結晶をろ別してトルエンで洗浄し、濃緑色結晶を0.58g(収率29%、HPLC純度100%)得た。得られた濃緑色結晶は、目的物である化合物No.10であることが確認された。得られた濃緑色結晶についての分析結果を以下に示す。
(1)1H−NMR(CDCl3溶媒)
(ピークトップのケミカルシフトppm;多重度;プロトン数)
(1.60;m;4)、(1.83;m;4)、(2.40;m;4)、(3.29;s;6)、(4.02;t;4)、(4.06;s;10)、(4.08;d;4)、(4.12;t;4)、(7.21;t;2)、(7.27;t;2)、(7.30;d;2)、(9.20;d;2)
(2)IR吸収(cm-1)
2929、1610、1571、1483、1426、1393、1338、1210、1161、1135、1099
(3)UV吸収測定(クロロホルム溶媒)
濃度:3.0×10-6mol/l
λmax;582nm、ε;1.60×105
(4)分解温度(TG−DTA:窒素気流(100ml/分)中、昇温速度10℃/分)
219℃;ピークトップ
<ステップ1>中間体5の合成
窒素置換した反応フラスコに、2,3,3−トリメチルインドレニン3.2g(20mmol)、1−ヨードプロピルフェロセン7.8g(22mmol)及びジメチルアセトアミド1.0gを仕込み、100℃で4時間撹拌した。80℃に冷却して酢酸エチル30.8gを滴下し、30分間加熱還流した。室温に冷却し、析出した固体をろ別し、酢酸エチルによる洗浄、乾燥を経て、白色固体として目的物である中間体5の6.4g(収率63%)を得た。
窒素置換した反応フラスコに、ステップ1で得られた中間体5の6.4g(12mol)及びエタノール13gを仕込み、均一に混合した。トリエチルアミン1.9g(19mmol)、続いてスクエア酸ジブチルエステル2.8g(12mmol)を滴下し、室温で一晩撹拌した。析出した固体をろ別し、メタノールで洗浄して、乾燥して黄色固体として目的物である中間体6の4.5g(収率66%)を得た。
窒素置換した反応フラスコに、ステップ2で得られた中間体6の4.5g(8.3mmol)、35%塩酸0.15g(4.2mmol)、酢酸8g及び水8gを仕込み、3時間加熱還流した。室温に冷却後、析出した固体をろ別して、メタノールで洗浄後乾燥し、緑色結晶として目的物である中間体7の3.7g(収率93%)を得た。
窒素置換した反応フラスコにステップ3で得られた中間体7の1.9g(3.9mmol)、1−メチルインドール0.51g(4.3mmol)及びブタノール6.6gを仕込み、85〜90℃で7時間撹拌した。室温に冷却後、溶媒を留去し、カラム精製(シリカゲル、アセトン:クロロホルム=1:9)を行った後、クロロホルム/酢酸ブチル混合溶媒から再結晶を行い、ろ過、酢酸ブチルによる洗浄を経て、緑色固体を1.4g(収率60%、HPLC純度100%)得た。得られた緑色固体は、目的物である化合物No.8であることが確認された。得られた緑色固体についての分析結果を以下に示す。
(1)1H−NMR(DMSO溶媒)
(ピークトップのケミカルシフトppm;多重度;プロトン数)
(1.77;s;6)、(2.04;m;2)、(2.40;t;2)、(3.92;s;3)、(4.02;t+t;4)、(4.09;s;5)、(4.35;t;2)、(6.11;s;1)、(7.25−7.67;arom;8)、(8.38;s;1)
(2)IR吸収(cm-1)
2952、1610、1581、1482、1449、1376、1322、1253、1156、1141、1099
(3)UV吸収測定(クロロホルム溶媒)
濃度:3.5×10-6mol/l
λmax;590nm、ε;1.85×105
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
273℃;ピークトップ
窒素置換した反応フラスコに製造例3のステップ3で得られた中間体7の1.8g(3.8mmol)、5−フルオロインドール0.51g(3.8mmol)及びブタノール6.8gを仕込み、85〜90℃で7時間撹拌した。室温に冷却後、溶媒を留去し、カラム精製(シリカゲル、アセトン:クロロホルム=1:3)を行った後、クロロホルム/酢酸エチル混合溶媒から再結晶を行い、ろ過、酢酸エチルによる洗浄、乾燥を経て、緑色固体を1.0g(収率44%、HPLC純度100%)得た。得られた緑色固体は、目的物である化合物No.7であることが確認された。得られた緑色固体についての分析結果を以下に示す。
(1)1H−NMR(DMSO溶媒)
(ピークトップのケミカルシフトppm;多重度;プロトン数)
(1.77;s;6)、(2.04;m;2)、(2.41;t;2)、(4.01;t+t;4)、(4.12;s;5)、(4.35;t;2)、(6.13;s;1)、(7.05−7.69;arom;7)、(8.38;s;1)、(12.3;s;1)
(2)IR吸収(cm-1)
3448、2955、1604、1572、1483、1449、1389、1321、1252、1179、1141、1095
(3)UV吸収測定(クロロホルム溶媒)
濃度:3.5×10-6mol/l
λmax;576nm、ε;1.52×105
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
275℃;ピークトップ
上記の製造例1で得た化合物No.1、製造例2で得た化合物No.10、並びに以下に示す比較化合物1及び2について、20℃でのメチルエチルケトンへの溶解性を評価した。評価は、シアニン化合物を0.1〜0.3重量%の濃度範囲で、0.05重量%刻みでメチルエチルケトンに加え、溶解、不溶を観察することにより行った。結果を表1に示す。
エチルメチルケトンと2,2,3,3−テトラフルオロプロパン−1−オールとの体積比1:1の混合溶媒を用いて、表2に記載のシアニン化合物の1重量%溶液を調製した。これらの溶液を用いて、20×20mmのポリカーボネート板上に2000rpm、60秒でスピンコートを行い試験片をそれぞれ作成した。得られた試験片についてUV吸収スペクトルを測定した後、該試験片に55000ルクスの光を照射し、照射前のUV吸収スペクトルのλmaxでの吸光度に対する照射後の吸光度残率が50%になるまでの時間を測定した。結果を表2に示す。
下記の配合をプラストミルで260℃にて5分間溶融混練した。混練後、直径6mmのノズルから押出し水冷却ペレタイザーで色素含有ペレットを得た。このペレットを電気プレスを用いて250℃で0.25mm厚の薄板に成形した。この薄板を(株)日立製作所スペクトロフォトメーターU−3010で測定したところ、λmaxが589nmで半値巾が28nmであった。
ユーピロンS−3000 100g
(三菱瓦斯化学(株)製;ポリカーボネート樹脂)
化合物No.1 0.01g
化合物No.1の代わりに化合物No.10を用いた以外は、実施例1と同一の方法で薄板を成形し測定を行ったところ、λmaxが582nmで半値巾が32nmであった。
化合物No.1の代わりに下記[化25]に示す比較化合物No.3を用いた以外は、実施例1と同一の方法で薄板を成形し測定を行ったところ、λmaxが596nmで半値巾が64nmであった。
下記の配合にてUVワニスを作成し、易密着処理した188ミクロン厚のポリエチレンテレフタレートフィルムに、該UVワニスをバーコーター#9により塗布した後、80℃で30秒乾燥させた。その後、赤外線カットフィルムフィルター付き高圧水銀灯にて紫外線を100mJ照射し、硬化膜厚約5ミクロンのフィルムを得た。これを(株)日立製作所スペクトロフォトメーターU−3010で測定したところ、λmaxが590nmで半値巾が28nmであった。
アデカオプトマーKRX−571−65 100g
(旭電化工業(株)製UV硬化樹脂、樹脂分80重量%)
化合物No.1 0.5g
メチルエチルケトン 60g
化合物No.1の代わりに化合物No.10を用いた以外は、実施例3と同一の方法でフィルムを作成し測定を行ったところ、λmaxが583nmで半値巾が31nmであった。
化合物No.1の代わりに比較化合物No.3を用いた以外は、実施例3と同一の方法でフィルムを作成し測定を行ったところ、λmaxが596nmで半値巾が65nmであった。
下記の配合にてバインダー組成物を作成し、易密着処理した188ミクロン厚のポリエチレンテレフタレート(PET)フィルムに、該バインダー組成物をバーコーター#9により塗布し、80℃で30秒乾燥させた。その後、このフィルムを0.9mm厚アルカリガラス板に100℃で熱圧着し、ガラス板とPETフィルムとの間のバインダー層に光吸収性色素を含有するPET保護ガラス板を作成した。これについて(株)日立製作所スペクトロフォトメーターU−3010で測定したところ、λmaxは590nmで半値巾は28nmであった。
アデカアークルズR−103 100g
(旭電化工業(株)製アクリル樹脂系バインダー、樹脂分50重量%)
化合物No.1 0.1g
化合物No.1の代わりに化合物No.10を用いた以外は、実施例5と同一の方法でPET保護ガラス板を作成し測定を行ったところ、λmaxは582nmで半値巾は32nmであった。
化合物No.1の代わりに比較化合物No.3を用いた以外は、実施例5と同一の方法でPET保護ガラス板を作成しを行ったところ、λmaxが596nmで半値巾が64nmであった。
化合物No.1を用い、前記評価例2と同様にして試験片を作成した。この試験片について、薄膜の吸収UVスペクトル及び入射角5°の反射光のUVスペクトルを測定したところ、吸収λmaxは613nmであり、反射光λmaxは650nmであった。
化合物No.10を用い、前記評価例2と同様にして試験片を作成した。この試験片について、薄膜の吸収UVスペクトル及び入射角5°の反射光のUVスペクトルを測定したところ、吸収λmaxは612nmであり、反射光λmaxは648nmであった。
Claims (8)
- 上記一般式(I)におけるY1及び上記一般式(II)におけるY2のどちらか一方が、上記一般式(IV)で表される置換基である請求の範囲第1項記載のシアニン化合物。
- 上記一般式(I)におけるY1及び上記一般式(II)におけるY2が、上記一般式(IV)で表される置換基である請求の範囲第1項記載のシアニン化合物。
- 上記一般式(I)におけるY1及び上記一般式(III)におけるY3のどちらか一方が、上記一般式(IV)で表される置換基である請求の範囲第1項記載のシアニン化合物。
- 上記一般式(I)におけるY1及び上記一般式(III)におけるY3が、上記一般式(IV)で表される置換基である請求の範囲第1項記載のシアニン化合物。
- 請求の範囲第1〜5項のいずれかに記載のシアニン化合物を含有してなる光学フィルター。
- 画像表示装置用である請求の範囲第6項に記載の光学フィルター。
- 基体上に光学記録層が形成された光学記録媒体の該光学記録層に用いられる、請求の範囲第1〜5項のいずれかに記載のシアニン化合物を含有してなる光学記録材料。
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PCT/JP2005/015055 WO2006035555A1 (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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CN (1) | CN1989208B (ja) |
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JP4986457B2 (ja) * | 2005-04-05 | 2012-07-25 | 株式会社Adeka | シアニン化合物、光学フィルター及び光学記録材料 |
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 |
WO2012029520A1 (ja) | 2010-09-03 | 2012-03-08 | 株式会社Adeka | 色変換フィルタ |
CN103930806B (zh) * | 2012-04-25 | 2016-11-23 | 株式会社艾迪科 | 波长截止滤光器 |
KR102443070B1 (ko) * | 2017-09-29 | 2022-09-16 | 후지필름 가부시키가이샤 | 편광판 보호막, 편광판, 및 액정 표시 장치 |
CN111770968B (zh) * | 2018-02-28 | 2022-10-28 | 富士胶片株式会社 | 树脂组合物、滤光器、图像显示装置、固体摄像元件及化合物 |
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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 |
JP2003035818A (ja) * | 2001-05-14 | 2003-02-07 | Sumitomo Chem Co Ltd | 映像表示機器用フィルター |
JP2003171571A (ja) * | 2001-09-28 | 2003-06-20 | Tamura Kaken Co Ltd | シアニン系化合物、その中間体、シアニン系色素、光学記録材料及び光情報記録媒体 |
JP2004195765A (ja) * | 2002-12-18 | 2004-07-15 | Taiyo Yuden Co Ltd | 光情報記録媒体 |
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JP4488762B2 (ja) * | 2003-04-04 | 2010-06-23 | 株式会社Adeka | 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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- 2005-08-18 CN CN2005800249973A patent/CN1989208B/zh not_active Expired - Fee Related
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JPS63138345A (ja) * | 1986-11-21 | 1988-06-10 | イーストマン コダック カンパニー | 写真像形成性システム |
JPS63142346A (ja) * | 1986-11-21 | 1988-06-14 | イーストマン コダック カンパニー | ネガ形フォトレジスト |
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 |
JP2003035818A (ja) * | 2001-05-14 | 2003-02-07 | Sumitomo Chem Co Ltd | 映像表示機器用フィルター |
JP2003171571A (ja) * | 2001-09-28 | 2003-06-20 | Tamura Kaken Co Ltd | シアニン系化合物、その中間体、シアニン系色素、光学記録材料及び光情報記録媒体 |
JP2004195765A (ja) * | 2002-12-18 | 2004-07-15 | Taiyo Yuden Co Ltd | 光情報記録媒体 |
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KR101226194B1 (ko) | 2013-01-24 |
TW200624513A (en) | 2006-07-16 |
KR20070057135A (ko) | 2007-06-04 |
CN1989208B (zh) | 2011-12-14 |
WO2006035555A1 (ja) | 2006-04-06 |
CN1989208A (zh) | 2007-06-27 |
JPWO2006035555A1 (ja) | 2008-05-15 |
TWI371471B (ja) | 2012-09-01 |
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