TWI376369B - - Google Patents
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- TWI376369B TWI376369B TW095128767A TW95128767A TWI376369B TW I376369 B TWI376369 B TW I376369B TW 095128767 A TW095128767 A TW 095128767A TW 95128767 A TW95128767 A TW 95128767A TW I376369 B TWI376369 B TW I376369B
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- TW
- Taiwan
- Prior art keywords
- group
- compound
- carbon
- alkyl group
- atom
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- -1 knot Chemical compound 0.000 claims description 122
- 230000003287 optical effect Effects 0.000 claims description 85
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 150000001450 anions Chemical class 0.000 claims description 21
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 239000011159 matrix material Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 description 101
- 150000001875 compounds Chemical class 0.000 description 91
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 238000010521 absorption reaction Methods 0.000 description 31
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 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 8
- 229920002678 cellulose Polymers 0.000 description 8
- 239000010419 fine particle Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000001913 cellulose Substances 0.000 description 7
- 235000010980 cellulose Nutrition 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 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 5
- 230000001050 lubricating effect Effects 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 5
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011247 coating layer Substances 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
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 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 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 229910052715 tantalum Inorganic materials 0.000 description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- UNIDEFGBIDZCJO-UHFFFAOYSA-N 1-sulfanylpurine Chemical compound SN1C=NC2=NC=NC2=C1 UNIDEFGBIDZCJO-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-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
- 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 2
- 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 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229940008309 acetone / ethanol Drugs 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 2
- 238000010835 comparative analysis Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 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 2
- 125000002704 decyl group Chemical group [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])* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 239000010955 niobium Substances 0.000 description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 229940068984 polyvinyl alcohol Drugs 0.000 description 2
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- CSUFEOXMCRPQBB-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropan-1-ol Chemical compound CC(F)(F)C(O)(F)F CSUFEOXMCRPQBB-UHFFFAOYSA-N 0.000 description 1
- TXOZSRCVHASUCW-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropan-1-ol Chemical compound OC(F)CC(F)(F)F TXOZSRCVHASUCW-UHFFFAOYSA-N 0.000 description 1
- IMSVBNQVZVQSND-UHFFFAOYSA-N 1,5-bis(sulfanyl)pentan-3-one Chemical compound SCCC(=O)CCS IMSVBNQVZVQSND-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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Classifications
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- G11B7/248—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 porphines; azaporphines, e.g. phthalocyanines
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Optical Filters (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
九、發明說明: 【發明所屬之技術領域】 本發明係關於一種薪結+ a Λ 新穎之吲却化合物、濾光器以及光學 δ己錄材料。該11引D朵介人% & 4 。物作為光學要素等較為有用。該吲 哚化合物,尤其是作盔 為用於圖像顯示裝置之濾光器所含之 紫外線吸收劑較為有用, 用又’對於用於光學記錄媒體之光 學記錄材料較為有用, 與 这光予5己錄媒體係具有可見以及近 紅外區域之波長’且 J猎由低述I雷射等實施高密度之光 學記錄以及再生者。 【先前技術】 』因光學記錄媒體通常具有記錄容量較大、非接觸下進行 。己錄或再生等良好特徵,故而受到廣泛普及。於觸謂、 CD-R、DVD_R等可寫—次型光碟中,使㈣聚光至光學記 錄層之微小面冑’改變光學記錄層之性狀進行記錄,並根 據記錄部分與未記錄部分之反射光量之*同而進行再生。 現在,於上述光碟中,用於記錄以及再生之半導體雷射 之波長,於CD-R令為750〜83〇 nm,DVD R中為62〇咖〜_ nm ’但為進-步增加容量’而研究有使用短波長雷射之光 碟,例如研究有使用380〜420 nm之光作為記錄光者。 於使用短波長雷射之光學記錄媒體中,形成光學記錄層 時,使用有各種化合物。例如,專利文獻丨中報告有偶氮化 合物,專利文獻2中報告有叶啉化合物,專利文獻3中報告 有三唑化合物之金屬錯合物。然而,該等化合物若作為; 於形成光學記錄層之光學記錄材料,則其吸收波長特性未 113344.doc 必適合。 另一方面,於液晶顯示裝置(LCD)、電漿顯示面板(PDP)、 電致發光顯示器(ELD)、陰極管顯示裝置(CRT)、螢光顯示 管、電場放射型顯示等用於圖像顯示裝置之濾光器中,使 用吸收300〜390 nm之波長的光之化合物作為紫外線吸收 劑。 例如’下述專利文獻4中報告有一種含有紫外線吸收劑, 且阻隔200〜410 nm之光的用於有機el顯示器元件之薄膜。 然而’該用於有機EL顯示器元件之薄膜中所使用之紫外線 吸收劑’若作為遽光器用之紫外線吸收劑,則其吸收波長 特性未必適合。 專利文獻1 :曰本專利特開2004-209771號公報 專利文獻2:日本專利特開2〇〇4_58365號公報 專利文獻3 :日本專利特開2〇〇4_174838號公報 專利文獻4 :曰本專利特開20044 〇2223號公報 發明所欲解決之問題 故而’本發明之目的在於提供—種化合物,其具有尤其 適合用於圖像顯示裝置用濾光器以及使用短波長雷射光之 光學記錄媒體的光學記錄材料所使用之光學要素的光學特 性。 【發明内容】 本發明者積極研究之結果發現,具有亞胺基結構之特定 °引"朵化合物具有滿足上述光學要素之吸收波長特性,從而 完成本發明。 113344.doc 1376369 錄材料。 [化1] 本發明係馨於上述知識而成者,其目的在於提供一種以 下述通式⑴表示之㈣化合物;含有該㈣化合物而形成 之遽光器;以及用於基體上形成有光學記錄層之光學記錄 媒體的該光學記錄層之含有該,朵化合物而形叙光學記
pAn* (式中’ R1以及R2分別獨立表示氪毋 丁風原子、碳原子數1〜30之烴 基或者以下述通式(Π)表示之取代基,R3以及r4分別獨立表 示碳原子數1〜10之烧基、碳原子數1,之烧氧基或者碳原 子數6〜3 0之芳基,R5、R6、…以片8 以及R分別獨立表示氫原子、 碳原子數1〜3 0之烴基、鹵辛®早
困I席子、每基 '硝基、氰基、NHR 或者NR’R” ’ R、R·以及R"分別撫 刀別獨立表示碳原子數1〜10之烷
基,R’以及R"亦可相互連接而 疋牧形成裱,R5以及R6、R6以及 R7、R7以及R8亦可分別相互遠技 連接而形成味;Anq表示q價之 陰離子,q表示1或2,〇袅+肢带— '、將電何保持為中性之係數) [化2]
(式中,Ra〜Ri分別獨立表示 基’該院基中之亞甲基亦可 氫原子或者碳原子數1〜6之烷 以或-CO-取代,Z表示直接 113344.doc 1376369 鍵結或者亦可具有取代基之碳原子數卜8之伸烷基,該伸烷 基中之亞甲基亦可以-0·、-S-、-CO-、_CO〇_、_〇c〇_、、 -NH-、-CONH-、-NHCO-、-N=CH·或者-CH=CH-取代,Μ 表示金屬原子)。 【實施方式】 以下,就本發明之吲哚化合物、以及含有該吲哚化合物 而形成之遽光器及光學記錄材料’基於較好之實施形態加 以詳細說明。 首先’就本發明之D引η朵化合物加以說明。 於以上述通式(I)表示之本發明之吲哚化合物中作為以 R、R、R5、R6、R7以及R8表示之碳原子數卜“之烴基, 可列舉甲基、乙基、丙基、異丙基、丁基、第二丁基、第 三丁基、異丁基、戊基、異戊基、第三戊基、己基、環己 基、環己基甲基、2-環己基乙基、庚基、異庚基、第三庚 基、正辛基、異辛基、第三辛基、2_乙基己基、壬基、異 壬基、癸基、十二烷基、十三烷基、十四烷基、十五烷基、 十六烧基、十七烷基、十八烷基等烷基,乙烯基、丨·甲基 乙烯基、2-曱基乙烯基、丙烯基、丁烯基 '異丁烯基、戊 烯基、己烯基、庚烯基、辛烯基、癸烯基'十五烯基、卜 苯基丙烯-3-基等烯基,苯基、萘基、2_甲基苯基、3_曱基 苯基、4-曱基苯基、4_乙烯基苯基、3_異丙基苯基、扣異丙 基苯基、4-丁基苯基、4_異丁基苯基、4_第三丁基苯基、4· 己基苯基、4-環己基苯基、4-辛基苯基、4-(2-乙基己基)苯 基、4-硬脂基苯基、2,3·二甲基苯基、2,4_二曱基笨基、 I I3344.doc 1376369 一曱基苯基、2,6-二甲基苯基、3,4_二曱基苯基、3,5二甲 基苯基、2,4-二第三丁基苯基、環己基苯基等烷基芳基苄 基、苯乙基、2-苯基丙烷·2_基、二苯基甲基、三苯基甲基、 笨乙烯基、肉桂基等芳基烷基等,該等以醚鍵及/或硫醚鍵 中斷者,例如2-曱氧基乙基、3_曱氧基丙基、4_甲氧基丁基、 2-丁氧基乙基、甲氧基乙氧基乙基 '曱氧基乙氧基乙氧基 • 乙基、3_甲氧基丁基、2_苯氧基乙基、3-苯氧基丙基、2_ φ 甲硫基乙基' 2-苯硫基乙基等。進而,該等基亦可以烷氧 基、烯基、硝基、氰基、鹵素原子等取代,以選自烷氧基、 烯基以及氰基之1種以上取代之情形時,含有該等取代基之 所有碳原子數最大為30。 ., 作為上述通式⑴中之以R3、R4、R、R·以及R"表示之碳原 ,· 子數1〜10之烷基,可列舉曱基、乙基、丙基、異丙基、丁 . 基'第二丁基、第三丁基、異丁基、戊基、異戊基、第三 戊基、己基、環己基、庚基、異庚基、第三庚基、正辛基、 • I辛基、第三辛基、2·乙基己基、壬基、癸基等,作為碳 原子數1〜10之烷氧基,可列舉子氧基、乙氧基、異丙氧基、 丙氧基、丁氧基、戊氧基、異戊氧基、己氧基、庚氧基' 辛氧基、2-乙基己氧基等,作為碳原子數6〜3〇之芳基,可 列舉苯基、萘基、2-甲基苯基、3_甲基苯基、4_曱基苯基、 4-乙烯基苯基、3-異丙基苯基、4•異丙基苯基、‘丁基苯基、 4-異丁基苯基、4-第三丁基苯基、4_己基苯基、4_^己基笨 基4·辛基苯基、4-(2_乙基己基)苯基、心硬脂基苯基、 二甲基苯基、2,4-二甲基苯基、2,5_二曱基笨基、^二甲 ]13344.doc -9- 1376369 基苯基' 3,4-二甲基苯基、3,5_二甲基苯基、^•二第三丁 基苯基、二第三丁基苯基、2,6•二·第三丁基苯基Μ. -第二戊基笨基、2,5_二第三戍基苯基、2,5_ 基、二異丙苯基苯基、環己基苯基、聯苯基、; 甲基苯基、节基、苯乙基、2_苯基丙炫·2·基、二笨基甲基、 二苯基甲基、苯乙烯基、肉桂基等。 作為上述通式⑴中之以r5、r6、r7以及r8表示之齒素原 子’可列舉氟、氣、溴、碘β 作為上述通式⑴中之R,以及R"連接所形成之環可列舉 娘咬環、料環…比略燒環、嗎嘛環等,作為r^r6、r6 與R7以及R7與…連接所形成之環,可列舉環丁稀環、環戍 烯環、環已埽環、苯環、D比咬環等。 作為上述通式(11)中之以Ra〜R>示之碳原子數W之烧 基一可列舉甲基、乙基、丙基、異丙基、丁基、第二丁基、 第一丁基、異丁基、甲氧基、乙氧基、丙氧基、異丙氧基、 甲氧土甲基[氧基甲基、2_甲氧基乙基、乙醯基' 卜羰基 乙基,乙醯基甲基、幾基丙基、2·氧代丁基、2·乙酿基乙 基1叛基異丙基等’作為亦可含有以z表示之取代基之碳 原子數1〜8之伸烷基’可列舉亞曱基、伸乙基、伸丙基、甲 基伸乙基、伸丁基、”基伸丙基、2·甲基伸丙基、“2-二 甲基伸丙基、1>3·二甲基伸丙基、卜甲基伸丁基、2甲基伸 丁基3·甲基伸丁基、4_甲基伸丁基、2,4·二甲基伸丁基、 1’3-二甲基伸丁基、伸戊基、伸己基、伸庚基、伸辛基、乙 二基、丙烧·2’2-二基、伸乙稀基、伸丙稀基、亞甲 II3344.doc
基氧基、伸乙基氧基、氧基亞甲基、硫代亞甲基、幾基亞 甲基、叛氧基亞甲基、亞甲基幾氧基、續酿基亞甲基、胺 基亞甲基、乙醯基胺基、伸乙基叛酿胺、乙烷酿亞胺基等, 作為以Μ表示之金屬原子,可列舉鐵、銘、錄鋼 '辞、 鋁、鈦、鍅、釩、鈮、钽、鉻、鉬、鎢、鉞、錳、釕、鎵、 銦、矽、鍺、錫、銻、鉍、金、銀、鈀、铑、鉑、銥、釔、 鋼、錯 '敍、飯、亂、鋼、欽、H 於上述通式(I)中,作為以Anq-表示之陰離子,例如作為 價者,可列舉氣陰離子、溴陰離子 '碘陰離子、氟陰離 子等齒素陰離子;過氯酸陰離子 '氯酸陰離子、硫氰酸陰 離子、六氟化磷陰離子、六氟化銻陰離子、四氟化硼陰離 子·#無機系陰離子;苯續酸陰離子、甲苯續酸陰離子、二 氟曱烷磺酸陰離子、二苯基胺_4_磺酸陰離子、2_胺基_4_甲 基-5-氣苯磺酸陰離子、2·胺基-5-硝苯磺酸陰離子等有機磺 酸陰離子;辛基磷酸陰離子、十二烷基磷酸陰離子、十八 烧基磷酸陰離子、苯基磷酸陰離子、壬基苯基磷酸陰離子、 2,2'-亞曱基雙(4,6-二第三丁基苯基)膦酸陰離子等有機磷 酸系陰離子’雙三氟甲基續醯基醯胺陰離子、雙全敦丁烧 磺醯基醯胺陰離子、全氟-4·乙基環己烷磺酸陰離子、四(五 氟苯基)硼酸陰離子、三(氟烷墓磺醯基)碳陰離子等,作為 二價者,例如可列舉苯二磺酸陰離子、萘二磺酸陰離子等。 又,亦可根據需要亦可使用具有使處於激發狀態之活性分 子去激發(猝滅)之功能的泮滅劑陰離子,或者環戊二烯環上 具有叛基或膦酸基、確醯基等陰離子性.基團之二茂鐵、二 J13344.doc 茂釕(Rutheocene)等金屬茂化合物陰離子等。 作為上述淬滅劑陰離子,例如可列舉以下述通式㈧、⑻ 或下述式⑹表示者,如揭示於日本專利特開昭60-234892 號公報、日本專利特開平5_43814號公報、日本專利特開平 5.305770號公報、日本專利特開平6 23_號公報、日本專 利特開平9·3〇9886號公報、日本專利㈣平9則㈣公 報、日本專利特開平1()·45767號公報、日本專利特開平 η·2〇8ΐΐ8號公報、日本專利特開2〇〇〇168237號公報日本 專利特開2GG2-2G1373號公報、日本專利特開·22〇6〇6ι 號公報 '日本專利特開2〇〇5·2974〇7號公報 '日本專利特公 平7-96334號公報、國際公開烟咖號公報等所揭示之陰 離子。 [化3]
(式中,X表示鎳原子或者鋼原子,R9以及r1G分別獨立表示 鹵素原子、碳原子數1〜8之烷基、碳原子數6〜3〇之芳基或者 -SOyG基,G表示烷基、亦可以齒素原子取代之芳基、二烷 基胺基、二芳基胺基、哌啶基或者嗎啉基,a以及b分別表 示0〜4。又,R丨丨、R〗2、Ru以及rM分別獨立表示烷基烷 基笨基、烧氧基苯基或者函化笨基)。 [化4] 113344.doc •12·
1376369
數f 3本:明之’朵化合物中,上述通式⑴中,R1為碳原子 ㈤ ’尤其是碳原子數1〜8之院基或者碳原子數
b ^芳基者,R2為氫原子或者碳原子數丨〜儿之烴基,尤 其是;原子、碳原子數1〜8之烷基或者碳原子數6〜13之芳基 者;R43為碳原子數1〜10之烷基,尤其是碳原子數i〜4之烷基 者;R4為碳原子數卜⑺之烷基,尤其是碳原子數丨〜4之烷基 者’該等於成本以及光學特性方面良好,故而較好。
[化5]
故而’作為本發明之吲哚化合物之具體例,可列舉下述 化合物No· 1〜24。
113344.doc -13- 1376369 化合构Me. 10
[化6] 化合物No. 12
fit
Η ^ 化合构Ν〇. 21 化合物Μ〇·22
[化7] 113344.doc -14-
1376369 對於以上述通式(i)表示之本發明之吲哚化合物之製造方 法,並未加以特別限定,可藉由利用眾所周知之普通反應 之方法獲得,但作為製造方法,例如獲得含有一價陰離子 之吲哚化合物之情形時,可列舉如下述[化6]所示之路徑般 合成之方法。 [化8]
(式中,Rl、R2、R3、R4、R5、R6、R7、R8、X、γΐ 以及 Y2 與上述通式(I)相同,Hal表示鹵素原子,表示陰離子) 本發明之吲哚化合物,其作為藉由吸收特定波長、尤其 113344.doc -15- 1376369 是320〜420 nm波長之光, 用。作為光學要素之例子, 吸收劑、用於形成光碟等光 學記錄劊等。 又,本發明之十朵化合物,除用於光學要素以外,亦可 用於醫藥品、t藥、香料、染料#合成中間體,或者各種 功能性材料等中》
其次,就本發明之濾光器加以說明。
而發揮功能之光學要素較為有 可列舉包含於濾光器之紫外線 學記錄媒體之光學記錄層的光 本發明之遽光器含有本發明之% _化合物。本發明之巧 °朵化合物,因其於340〜390⑽具有吸收最大波長,並可吸 收、阻隔4H) nm以下之紫外線以及一部分可見光線進行阻 隔,故而含有本發明之Μ化合物之本發明之據光器,其 尤其適合用作顯示圖像之高品質化中所使用之用於圖像顯 不裝置的濾光器。本發明之濾光器,除用於圖像顯示裝置 用以外,亦可用於分析裝置、半導體裝置製造、天文觀測、 光通信、眼鏡透鏡等各種用途中。 本發明之濾光器通常配置於顯示器之前面。例如,本發 明之濾光器亦可直接貼附於顯示器之表面,於顯示器前嗖 置有前面板之情形時,亦可貼附於前面板之表側(外側)或= 背側(顯示器侧)》 作為本發明之濾光器之代表性構成,可列舉根據需要 透明支持體上設置下塗層、反射防止層、硬塗層、潤.骨 等各層者。作為使本發明之濾光器含有本發明之巧丨嘴化 物、或本發明之吲哚化合物以外之色素化合物、 合種穩 Ϊ *3344.doc -16- 劑等任意成分的方法,也丨l 1 例如可列舉(1)包含於透明支持體或 任意各層之方法, (2)塗層於透明支持體或任意各層之方 法’ (3):¾入選自透明支持體以及任意各層之任意鄰接兩者 間的黏者劑層之方法,, ()各層之外另外設置含有本發明之 引木化口物等光吸收劑等之光吸收層的方法等。 ;本發月之濾光盗中,本發明之吲哚化合物之使用量, 於滤光器之每單元面積中,通常^〜i〇〇〇mg/m2,較好的 是 5〜100 mg/m2, 田災用里不足1 mg/m2時,無法充分發 光吸收效果,當使用, 之色㈣強… "之情形時,可能膜 之色㈣強而導致顯示品質降低等,進而亦可 降低。 反
為使遽光器之每單分&接A 早7L面積中本發明之吲哚化合物之使用 量於上述範圍内,通常如下使用。例如,製造黏著劑層中 :有本發月之?卜木化合物之濾光器之情形時’相對於1〇〇質 量份丙稀酸系_著劑等黏著劑,添加較好之〇〇〇1〜〇〇5質量 伤本發明之。弓卜朵化合物以及較好之4〇〜遍質量份甲基乙美 嗣等溶劑,從而製作㈣,㈣清漆塗布於㈣密著處^ 之PET薄膜等透明支持體後,使其硬化,獲得具有厚产 0.1〜10微米之黏著劑層(硬化膜)的濾光器。 作為使本發明之十朵化合物以及任意成分包含於本發明 之慮先器之方法’採用上述⑴〜⑷之任何一種方法之情形 時’依據上述添加比例設定各成分之添加比例即可。 作為上述透明支持體之材料,例如可列舉 料匕乙酿基纖維素、^酿基纖維素(TAC)、_基2 I13344.doc -17· 1376369 素、丁醯基纖維素、乙醯基丙醯基纖維素、硝基纖維素等 纖維素酯;聚醯胺;聚碳酸酯;聚對苯二甲酸乙二醇s旨、 聚萘曱酸乙二醇酯、聚對苯二甲酸丁二醇酯、聚對笨二甲 酸環己二醇酯、聚-1,2·二苯氧基乙烷-4,4'-二羧酸乙二 能、聚對苯二甲酸丁二醇酯等聚酯;聚苯乙烯;聚乙稀、 聚丙烯、聚甲基戊烯等聚烯烴;聚甲基丙烯酸甲酯等丙稀 酸系樹脂;聚碳酸酯;聚颯;聚醚颯;聚醚酮;聚喊酿亞
胺;聚氧乙烯、降冰片烯樹脂等高分子材料。透明支持體 之透過率較好的是80%以上,尤其好的是86q/()以上。濁度較 好的是2%以下,尤其好的是1%以下。折射率較好的是 145〜1.70。 於該等透明支持體中,可添加紅外線吸收劑、無機微粒 子等’又,可對透明支持體實施各種表面處理。 作為上述無機微粒子,例如可列舉層狀黏土礦物、二氧 化硬、—氧化鈦、硫酸鋇、碳駿辦等。
作為上述各種表面處理,例如可列舉藥品處理、機械性 處理、電暈放電處理、火焰處理、紫外線照射處理、高頻 處理、輝光放電處理、活性電聚處理 '雷射處理、混酸處 理以及臭氧氧化處理等。 、叹直3有光吸收劑之光吸收層之情形時,上述_ 係用於透明支持體與光吸收層之間之層。上述下塗/ 成為含有破璃轉化溫度為备6代之聚合物之層、^ 層側之表面為粗面之層、或去人 A者a有與光吸收層之聚4 有親和性之聚合物的層。又, 下塗層’其設置於未言 113344.doc -18· 1376369 先吸收層之透明支持體之面,亦可為改善透明支持體與設 置於其上部之層(例如,反射防止層 '硬塗層)之接著力而設 置,亦可為改善用以接著渡光器與圖像顯示裝置的接著劑 與遽光器之親和性而設置。下塗層之厚度較好的是2.2〇 帥,更好的是5 nm〜5㈣,進而較好的是2()細〜2㈣特 別好的是SOnd㈣’最好的是8〇nm〜扇含有玻璃 轉化溫度為备6〇t之聚合物之下塗層,其以聚合物之黏 著性而接著透明支持體與薄膜層。玻璃轉化溫度為 ,〜6(TC之聚合物,例如可藉由氯乙烯、偏氯乙烯、乙酸 乙烯醋、丁二烯、氯丁橡膠、苯乙婦、氯丁二婦、丙婦酸 酉旨、甲基丙稀酸醋、丙稀腈或甲基乙稀越之聚合或該等之 共聚合而獲得。玻璃轉化溫較好的是5〇{>c以下,更好的是 贼以下,進而較好的是抓以下,特別好的是抑以下, 最好的是20。(:以下。下塗層之2,c下之彈性率較好的是 卜卿MPa,進而較好的是5〜_胸,最好的是1〇〜則 驗。光吸收層側之表面為粗面之下塗層,藉由於粗面上 形成光吸收層’而接著透明支持體與光吸收層。光吸收層 側之表面為粗面之下塗層,可藉由塗布聚合物乳膠而易於 形成。乳敎平均粒純好的是⑽〜⑽,進而較好的是 〇·〇5〜―作為與光吸收層之黏合劑聚合物具有親和性之 聚合物,可列舉丙稀酸樹脂、纖維素衍生物、明膠、路蛋 白、澱粉、聚乙烯醇、可溶性尼龍以及高分子乳膠等。又, 亦可於本發明之濾光器中設置兩層以上之下塗層。於下塗 層中’亦可添加使透明支持體膨潤之溶劑、極光劑、界面 113344.doc •19- 活性劑、帶電防止劑、塗布助劑以及硬膜劑等。 於上述反射防止層中,必須設置低折射率層。低折射率 層之折射率低於上述透明支持體之折射率。低折射率層之 折射率,較好的是L20〜⑸,進而較好的是低 折射率層之厚度’較好的是50〜彻nm,進而較好的是 5〇〜200 nm。低折射率層,可形成為含有折射率較低之含敦 聚合物之層(揭示於日本專利特開昭叫侧號、日本專利 特開平3_U咖號、日本專利特開平6·⑽挪、日本專利 特開w號、日本專利特開平7摘刚號之各公 報),藉由溶膠-凝膠法獲得之層(揭示於曰本專利特開平 m、日本專利㈣平6_299q9丨號、日本專利特開平 '168003號之各公報)、或者含有微粒子之層(揭示於曰本專 利特a昭6G 5925G號 '日本專利特開平513⑵號、日本專 利特開平6-56478號、日本專利特開平7·92則號、日本專利 特開平9-288201號之各公報)。含有微粒子之層中,可作為 微粒子間或微粒子内$ Μ π ' ’ 于円之被孔,於低折射率層中形成空隙。 含有微粒子之層,齡辟目士, 权子的疋具有3〜5〇體積%之空隙率,進 而較好的是具有5〜35體積%之空隙率。 為防止廣泛波長區域之反射,較好的是於上述反射防止 層中,除低折射率層以外,積層折射率較高之層(中.高折射 率層)。向折射率層之折射率’較好的是1.65〜2.40,進而較 好的是1 ·70〜2.20。蔣φ姑私屯a , 將中折射率層之折射率調整為低折射率 層之折射率與高折射率層之折射率之中間值。中折射率層 之折射率,較好的是15g〜19q,進而較好的 113344.doc •20· 1376369 中0高折射率層之厚度,較好的是5 nm〜100叫’進而較好 10 μηι,最好的是3〇 nmy 。中高折射 之濁度,較好的是⑽以下,進而較好的是3%以下 二 是1%以下。中.古从“方。 开的 n折射率層,可使用具有折射率比較高之 二物黏而形成。作為折射率較高之聚合物,可列舉聚 本乙婦#乙歸共聚物、聚碳酸醋、三聚氛胺樹脂、苯盼 樹脂、環氧樹脂、藉由環狀(脂環式或芳香族)異氛酸酿 兀醇之反應而獲得之聚胺基 /、 心具有其他環狀(芳香 雜環式、脂環式)基之聚合物,或具有氟以外之齒 子作為取代基之聚合物折 …' — 义折射辜亦較南。夺可使用藉由導 雙鍵而貫現自由基硬化之單體的聚合反應而形成的聚合 物。 。 八為獲得進而較高之折射率,亦可於上述聚合物黏合劑中 为散無機微粒子。較好的是無機微粒子之折 =80〜2.80。無機微粒子,較好的是自金屬之氧化物或硫化 物形成。作為金屬之氧化物或硫化物,可列舉氧化欽⑽ 士。’金紅石、金紅石/銳鈦礦之混晶、銳鈦礦、非晶結構)、 氧化錫、氧化銦、氧化鋅、氧化錯、硫化 別好的是氧化鈦、氧化錫以及氧化銦。無機微粒;以該= 金屬之氧化物或硫化物作為主成分,進而 〆一 士 ^ 3 ^ί. 所謂主成分’係指構成粒子之成分中含量(重量叫較多 之成分。作為其他元素,可列舉Ti、Zr、 亦可使用可分散於溶劑、或其本身為液狀之無機材:專例 H3344.doc '與配位性化合物鍵結 無機聚合物,以被膜形 如各種元素之院醇鹽、有機酸之鹽 之配位化合物(例如’螯合物)、活性 成性而形成中·高折射率層。 對於上述反射防止層之矣而 <表面可賦予防眩功能(使入射光 於表面散射’從而防止膜周囹旦1士 I联周圍厅、色轉移至膜表面之功能)。 例如於透U膜之表面形成微細凹凸,從而於其表面形 成反射防止層,或者形成反射防止層後,藉由壓花親於表 面形成凹凸,藉此可獲得具有防眩功能之反射防止層。具 有防眩功能之反射防止層通常具有3〜3〇%之濁度。 上述硬塗層,具有高於上述透明支持體之硬度之高度。 硬塗層較好的是含有經交聯之聚合物。硬塗層可使用丙烯 酸系、胺基曱酸酯系、、環氧系之聚合物,寡聚物或單體(例 如,1外線硬化型樹脂)等形成。亦可自二氧化矽系材料形 成硬塗層。 亦可於上述反射防止層(低折射率層)之表面形成潤滑 層。潤滑層具有對於低折射率層表面賦予滑性,從而改善 耐損傷性之功能。潤滑層可使用聚有機矽氧烷(例如,矽 ’由)、天然蠘、石油躐、高級脂肪酸金屬鹽、氟系潤滑劑或 其衍生物等形成。潤滑層之厚度,較好的是2〜2〇 nm。 上述各層之外另外設置光吸收層之情形時,既可直接使 用本發明之吲哚化合物,亦可使用黏合劑。作為黏合劑, 例如可使用明膠、酪蛋白、澱粉、纖維素衍生物、褐藻酸 等天然高分子材料,或者聚甲基丙烯酸甲酯、聚乙烯酵縮 丁酸、聚乙烯吡咯烷酮、聚乙烯醇、聚氣乙烯、苯乙烯-丁 U3344.doc -22- 1376369 二歸共聚物、聚苯乙稀、聚碳酸醋、聚醯胺、聚胺基甲酸 酯、聚酯、聚脲等合成高分子材料。 上述下塗層、反射防止層、硬塗層、潤滑層、光吸收層 等可藉由通常之塗布方法形成。作為塗布方法可列舉^ /貝塗布法、氣刀塗布法、淋幕塗布法、滚筒塗布法、線棒 塗布法、凹版印刷塗布法、使用漏斗之擠出塗布法(揭示於 美國專利第2觀94號說明書)等。亦可藉由同時塗布而形 成兩層以上之層。關於同時塗布法,例如揭示於美國專利 第2761791號、美國專利第294刪號、美國專利第35剛7 號、美國專利第3526528號之各說明書以及原崎勇次著..塗 層工程253頁(1973年’朝倉書店發行)。 其次,就本發明之光學記錄材料加以說明。 本發明之光學記錄材料,係含有本發明之吲哚化合物, 且用於形成光學記錄媒體之光學記錄層者,可根據所含之 叫丨哚化合物之光吸收特性而適用於各種光學記錄媒體。本 發明之光學記錄材料中’尤其適合於波長為38〇nm〜42〇⑽ 之短波長雷射用光碟者,係所含之十朵化合物於溶液狀態 之光吸收特性中’於320〜420 mm之範圍内具有最大吸收波
長WX者。又’關於吸收強度,當Xmax下之ε小於UxW 時存有6己錄靈敏度降低之可能性,故而較好的是】加1〇4 以上。上述㈣化合物之溶液狀態下之人霞以及以測定, 可根據吊用方法’選擇試料溶液之濃度、測定時使用之溶 劑等而進行。 關於使用合有上述卜朵化合物之本發明之光學記錄材料 113344.doc -23- C S ) 1376369 錄層的方法,並未加以特別限 ••於甲醇、乙醇等低級醇類; 丁基溶纖劑、二乙二醇丁鍵等 甲基異丁基嗣、環己嗣、二 形成光學記錄媒體之光學記 制。通常,可列舉如下方法 甲基溶纖劑、乙基溶纖劑、 醚醇類;丙酮、甲基乙基酮 丙酮醇等酮類;乙酸乙酯、 乙^丁酯 '乙酸甲氧基乙酯等 醋類,丙稀酸乙g旨、丙條龄T 枯 ^ 輝酸丁 g日等丙烯酸酯類;2,2,3,3-四 氟丙醇等氟化醇類;苯、甲裳 一 T本一甲苯等烴類;二氯甲烷、
二氣乙燒、氯仿等氯化烴類辇毺 工頸寺有機溶劑中,溶解本發明之 吲Β朵化合物以及各種化人抓 、 σ物’將如此獲得之溶液於基體上 以旋塗、噴射、浸珍黧 踅4進仃塗布之濕式塗布法、蒸鍍法、 及濺射法等。 上述光子6己錄層作為薄膜而形成,其厚度通常〇 〇 叫較為合適,較好的是Q.G1〜5 _之範圍。 人百本發月之光學s己錄材料中之本發明之吲哚化合物之 含量’較好的是於本發明之光學記錄材料所含之固形分中 100重里%。上述光學記錄層’較好的是以光學記錄 曰3有50刚質$ %之以上述通式(I)表*之十朵化合物 的方式形成’為形成如此之吲哚化合物含量之光學記錄 二曰進而較好的是本發明之光學記錄材料以本發明之光學 、、、材料所3之固形分為基準,含有5〇〜質量%之以上 述通式⑴表示之。5丨嗓化合物。 本發明之光學記錄材料’除本發明之吲哚化合物以外, :了根據需要含有菁系化合物、偶氮系化合物、酞菁系化 氧右系化合物、Squarilium系化合物苯乙烯系化合 H3344.doc •24- 1376369 物、。卜吩系化合物、Azlenium系化合物、
系化合物、吡喃鑷系化合物、硫代吡喃鎬系化合物、三芳 基曱烷系化合物、二苯基曱烷系化合物、四氫膽鹼系化合 物、靛酚系化合物、蒽醌系化合物、萘醌系化合物、氧雜 蒽系化合物、嗟嗪系化合物"丫咬系化合物,系化合 物、螺吡喃系化合物、芴系化合物、若丹明系化合物等通 常用於光學記錄層之化合物;聚乙燁、聚、聚苯乙稀、 聚碳酸類;界面活性劑;帶電防止劑;潤滑劑; 阻燃劑,受阻胺等自由基捕捉劑;二茂鐵衍生物等訊坑形 成促進劑;分㈣;氧化防止劑;交聯劑;耐光性賦予劑 等。進而,本發明之光學記錄材料,亦可含有芳香族亞硝 基化合物、銨化合物、亞胺離子化合物、雙亞胺離子化合 物、過渡金屬整合物等,作為單態氧等猝滅劑,亦可使用 猝滅劑陰離子。於本發明之光學記錄材料中,較好的是使 用於本發明之光學記錄材料所含之固形分中佔〇〜5〇重量% 範圍之量的該等各種化合物。 設置如此之光學記錄層之上述基體之材質,若對於寫入 (記錄)光以及讀出(再生)光實質上為透明者,則並無特別限 制,例如可使用聚甲基丙烯酸甲酯、聚對苯二甲酸乙二醇 酉旨、聚碳酸醋等樹脂’玻璃等。x,其形狀,根據用料 使用磁帶狀、滾筒狀、皮帶狀、碟狀等任意形狀者。 又,於上述光學記錄層上,既可使用金、銀、鋁、銅等, 藉由蒸鍍法或濺射法形成反射臈,亦可藉由丙 紫外線硬化性樹脂等形成保護層。 曰 I I3344.doc ^25 - S 3 1376369 實施例 以下,藉由實施例以及比較例進一步詳細說明本發明。 然而’本發明並非限定於下述實施例等。 [實施例1]化合物No. 1之合成 於經氮置換之反應燒瓶中,加入10 ml二甲基甲醯胺 (DMF)以及80 ml氣仿,於冰浴下滴加6.91 g(45.1 mmol)鱗 醯氣,冰浴下攪拌1小時》於冰浴下滴加40 ml氯仿中溶解 有3.94 g(30.0 mmol)l-曱基吲哚者’加熱回流3小時。冷卻 至室溫’並將反應液緩慢滴加至23.1 g( 126 mmol)六氟化磷 酸鉀之400 ml水溶液中,於室溫下攪拌2小時。過濾分離析 出物,使用200 ml甲醇於室溫下攪拌30分鐘,進行清洗。 經由過濾、乾燥,獲得9.32 g(收率93.4°/。)粉紅色固體。確 認所得之粉紅色固體為目標物之化合物Ν〇· 1。以下表示關 於所得化合物No. 1之分析結果。 (1) 〗H-NMR(ppm、DMSO溶劑) 3.5 7(s ; 3H)、3.74(s ; 3H)、4.01(s ; 3H)、7.39-7.50(m ; 2H)、 7.26-7.65(m; 1H)、8.00-8.10(m; 1H)、8.70(s; 1H)、9.12(s ; 1H) (2) IR吸收(cm·1) 3168、1647、1536、1466、1402、1349、1256、1113、838、 758 (3) UV吸收測定(丙酮溶劑)
Xmax : 345.0 nm,ε : 1.86x 104(濃度 6·68χ 1 Ο·6 mol/1) (4) 分解溫度(TG-DTA : 100 ml/分鐘氮氣流中,升溫i〇°c/ 113344.doc -26- (S ) 分鐘) 295.8°C :熔點,326_7°C :質量減少開始點 [實施例2]化合物No. 2之合成 於經氮置換之反應燒瓶中,加入1〇 ml DMF以及80 ml氣 仿,於冰洛下滴加6.90 g(45.0 mmol)填酿氯,冰浴下搜拌1 小時。於冰浴下滴加40 ml氣仿中溶解有6 22 g(3〇 〇 mm〇1)1-曱基·2-苯基。引哚者,加熱回流3小時。冷卻至室溫,將反應 液緩慢滴加至20.0 g( 109 mmol)六氟化磷酸鉀之4〇〇 ml水溶 液中’於室溫下攪拌3〇分鐘。除去水層,添加4〇〇 mi水於 至溫下攪拌30分鐘後’過濾分離析出物,並使用15 0 ml甲 醇於至溫下搜拌3 〇分鐘’進行清洗。經由過渡、乾燥,獲 得灰白色固體。自乙腈/乙醇混合溶劑進行再結晶,獲得5 〇6 g(收率4 1.5。/〇)灰白色固體。確認所得之灰白色固體為目標 物之化合物No. 2。以下表示所得化合物No. 2之分析結果。 (1) 】H-NMR(ppm、DMSO溶劑) 3.53(s ; 3H)、3.68(s ; 3H)、3.82(s ; 3H)、7.45-7.55(m ; 2H)、 7.58-7.75(m ; 5H)、7.83(d ; 1H、J=7.8Hz)、7.88(d ; 1H、 J=7.6Hz) ' 8.51(s ; 1H) (2) IR吸收(cm·1) 3430、1656、1490、1474、1463、1391、1120、842、795、 754 、 705 (3) UV吸收測定(丙酮溶劑)
Xmax : 348.5 nm,ε : Ι.74χ104(濃度 1.93xl0·6 mol/1) (4) 分解溫度(TG-DTA: 100 ml/分鐘氮氣流中,升溫1〇。〇/ 113344.doc •27- 分鐘) 162.6°C :熔點,332 9〇c :質量減少開始點 [實施例3]化合物No. 3之合成 於經氮置換之反應燒瓶中,於冰浴下加入15狀4 _1)Ν,Ν·正二丁基甲酿胺以及521 g(34 〇咖〇1)麟酿氯, 冰浴下授拌1小時。於冰浴下添加2 62 g(2〇 〇 ·〇ΐ)ι •甲基 引木’於100 c下攪拌3小時。冷卻至室溫,餾去N,N正二 丁基曱醢胺後,添加15.3 g(95.4 mmol)六氟化磷酸鉀進行均 勻混合。添加150 ml水於室溫下攪拌3〇分鐘後,過濾分離 析出物,並使用100 ml曱酵於室溫下攪拌3〇分鐘,進而添 加50 ml水,於室溫下攪拌3〇分鐘進行清洗。經由過濾、乾 燥,獲得黃土色固體。自乙腈/曱醇混合溶劑進行再結晶, 經由過濾、乾燥,獲得2.90 g(收率34.8%)淡粉紅色固體。 確認所得之淡粉紅色固體為目標物之化合物No. 3。以下表 示所得化合物No· 3之分析結果。 (1) 丨H-NMR(pρm'DMSO溶劑) 〇.96(t ; 3H ; J=7.3Hz) ' 0.97(t ; 3H ; J=7.3Hz) ' 1.36(tq ; 2H; J = 7.6、7.3Hz)、1.5 2(tq; 2H; J=7.8、7.6Hz)、1.70-1.89(m; 4)、3.85-3.99(m ; 4)、4.05(s ; 3H)、7.45(dd ; 1H、J=6.6、 3.9Hz)、7.46(dd ; 1H、J=6.6、3.7Hz)、7.68-7.80(m ; 1H)、 8.08-8.20(m ; 1H) ' 8.56(s ; 1H) ' 9.08(s ; 1H) (2) IR吸收(cm·1) 2955、2874、1639' 1532、1476、1352、1256、1114、834 ' 751 113344.doc -28- 1376369 (3)UV吸收測定(氣仿溶劑)
Xmax : 357.0 nm,ε : 2.04xl04(濃度 5.64X10·6 mol/1) ⑷分解溫度(TG-DTA : 100 ml/分鐘氮氣流中,升溫1〇口 分鐘) 179.7°C :熔點,307.8°C :質量減少開始點 [實施例4 ]化合物N 〇. 4之合成 於經氮置換之反應燒瓶中,於冰浴下加入丨5 g(95.4 mmol)N,N-正一 丁基甲酿胺以及5.21 g(34.0 mmol)填酿氯, 冰浴下攪拌1小時。於冰浴下添加6.22 g(30.0 mm〇l)l-曱基 吲哚’於100°C下攪拌4小時。冷卻至室溫,餾去N,N_正二 丁基曱酿胺後’添加25.0 g( 132 mmol)三氟甲烧石黃酸钟,進 行均勻混合。添加150 ml水於室溫下進行3〇分鐘超聲波照 射後’過滤分離析出物》自乙醇/二乙喊混合溶劑進行再結 晶,經由過濾、乾燥,獲得淡4.64 g(收率55.1 %)黃色固體。 確認所得之淡黃色固體為目標物之化合物Ν〇 4 β以不表示 所得化合物Ν 〇 · 4之分析結果。 (iyH-NMR(ppm、DMSO溶劑) 〇.94(t ; 3H ; J=6.6Hz)、0.96(t ; 3H ; J=7.iHz)、1.35(tq ; 2H , J = 7.6'7.6Hz) '1.51 (tq ; 2H ; J=7.6 > 7.6Hz)' 1.70-1.85(m; 4H)、3.85-3.95(m ; 4H)、4.05(s ; 3H)、7.35_7 5〇(m ; 2H)、 7.65-7.80(m; 1H)、8.05-8.20(m; 1H)、8.58(s; 1H)、9.09(s ; 1H) (2)IR吸收(cm·1) 2960、2874、1624、1588、1476、1464、1430、1265、1153、 II3344.doc -29- (S j 1376369 1032 ' 965 (3) UV吸收測定(氣仿溶劑)
Xmax : 356.5 nm,ε : Ι·84χ104(濃度 9.89xl(T6m〇i/i) (4) 分解溫度(TG-DTA: 100 ml/分鐘氮氣流中,升溫1〇〇c/ 分鐘) ll〇.3°C :熔點’ 287.TC :質量減少開始點 [實施例5 ]化合物Ν 〇. 5之合成 於經氮置換之反應燒瓶中’於冰浴下加入22.5 g( 143 mmoI)N,N-正二丁基甲醢胺以及7.82 g(51 〇 mm〇1)磷醯氣’ 冰浴下攪拌1小時。於冰浴下添加6.08 g(18.4 雙三氟曱基苯基)吲哚’於l〇〇°C下攪拌4小時。冷卻至室 溫,餾去N,N-正二丁基曱醯胺後’添加50.0g(272 mm〇1)六 說化構酸#f ’進行均勻混合。添加1L於水於室溫下搜拌3〇 分鐘後,除去水層,並使用1 L乙醇攪拌30分鐘進行清洗 後’過濾分離析出物。自丙酮/乙醇混合溶劑進行再結晶, 經由過濾、乾燥,獲得2.75 g(收率24.3%)無色透明針狀結 晶。’確認所得之無色透明針狀結晶為目標物之化合物N〇. 5。以下表示所得化合物No· 5之分析結果。 (lVH-NMR(ppm、DMSO溶劑) 0.96(t ; 3H ; J=7.6Hz)、0.99(t ; 3H ; J = 7.1Hz)、1.4〇(tq ; 2H; J=7.3、7.1Hz)、.1.48(tq; 2H; J=7.6' 7.6Hz)、1.78-1.95(m ; 4H)、4.05(t; 2 H; J = 7.6Hz)、4.11(t; 2 H; J=7.8Hz)、7.5i(dd ; 1H ; J = 8.5、7.1Hz)、7.55(dd ; 1H ; J=7.8、7.1Hz)、7.64(d ; 1 H; J=8.3Hz)、8.26(d; 1H; J=7.6Hz)、8.41(s; 1H)、8.60(s ; -30· 113344.doc 1376369 2H)、8.83(s ; 1H)、9.34(s ; 1H) (2) IR吸收(cm·1) 2967、2880、1646、1522、1475、1360、1282、1230、1192、 1146 、 843 、 825 、 762 (3) UV吸收測定(氯仿溶劑)
Xmax : 354.5 mm,ε : 1.92χ104(濃度 6.87xl(T6mol/l) (4) 分解溫度(TG-DTA : 100 ml/分鐘氮氣流中,升溫l〇°C/ 分鐘) 183.3°C :熔點’ 297.5*1::質量減少開始點 [實施例6 ]化合物N 〇 · 6之合成 於經氮置换之反應燒瓶中,於冰浴下加入22.5 g(143 mmol)N,N-正二丁基甲醯胺以及7.82 g(51.0 mmol)磷醯氯, 冰浴下攪拌1小時。於冰浴下添加6.22 g(30.0 mm〇l)i_曱基 -2-笨基吲哚’於i〇〇°c下擾拌4小時。冷卻至室溫,館去N,N_ 正一丁基甲酿胺後’添加50.0 g(272 mmol)六氟化碳酸奸, 進行均勻混合。添加1 L水於室溫下攪拌30分鐘進行清洗 後’過濾分離析出物。自丙酮/乙醇混合溶劑進行再結晶, 經由過濾、乾燥,獲得3.02 g(收率20_4%)淡綠色固體。確 認所得之淡綠色固體為目標物之化合物Ν〇· 6。以下表示所 得化合物N 〇. 6之分析結果》 (l^H-NMI^ppm、DMSO溶劑) 〇 8〇(t ; 3H ; J=7.3Hz) ' 0.90(t ; 3H ; J=7.3Hz) > 1.2〇(tq ; 2H; J=7.6、7.6Hz)、1.30(tq; 2H; J=7.6、7.6Hz)、1.65-1.79(m; 4H)、3.82(s ; 3H)、3.89(t ; 2H ; J=6.8Hz)、3.91(t ; 2H ; 113344.doc -31 · -(s ) 1376369 J = 6.8Hz)、7.49(dd; 1H; J=7.2、7.2Hz)、7.53(dd; 1H; J=7J、 7.1Hz)、7.57-7.63(m; 2H)、7.64-7.77(m; 3H)、7.80(d; 1H ; J = 7.8Hz)、7.85(d ; 1H ; J = 7.8Hz)、8.54(s ; 1H) (2) IR吸收(cm·1) 2960、2935、2874、165卜 1477、1464、1404、1368、1086、 838 > 802 ' 750 (3) UV吸收測定(氣仿溶劑)
Xmax : 352.5 nm,ε : 2·48χ104(濃度 4.07xl(T6mol/l) (4) 分解溫度(TG-DTA : 100 ml/分鐘氮氣流中,升溫l〇°C/ 分鐘) 100.4°C :熔點,304.9°C :質量減少開始點 [實施例7]化合物No. 21之合成 於經氮置換之反應燒瓶中,於冰浴下加入10 ml N,N-正二 曱基曱醯胺、80 ml氣仿以及6.74 g(44_0 mmol)鱗醯氯,冰 浴下攪拌1小時》於冰浴下添加10.5 g(29.3 mmol)l-丙基二 茂鐵基吲哚之40 ml氯仿溶液,加熱回流3.5小時。冷卻至室 溫’緩慢滴加至23.5 g(l27 mmol)六氟化構酸鉀之5〇〇 mi水 水溶液中’於室溫下攪拌1小時。過濾分離析出物,經由乾 燥,獲得16.2 g(收率99.4%)茶色固體。確認所得之茶色固 體為目標物之化合物No. 21。以下表示所得化合物N〇 21 之分析結果。 (lVH-NMI^ppm、DMSO溶劑) 1.48(dt ; 2H ; J = 7.3、7.3Hz)、1.90(dt ; 2H ; J = 7.3、7·3Ηζ)、 2.32(t,2H ; J=7.6Hz)、3.61(s ; 3H)、3.74(s ; 3H)、4.〇3(s ; 113344.doc -32- 1376369 5H)、3.98-4.05(m; 4H)、4.44(t; 2H; J=7.3Hz)、7.35-7.50(m ; 2H)、7.81(d; 1H; J=7.1Hz)、8.08(d; 1H; J=6.8Hz)、8.76(s ; 1H)、9.17(s ; 1H) (2) IR吸收(cm·1) 1654、1530、1404、1364 ' 1105、836 (3) UV吸收測定(氣仿溶劑)
Xmax : 353.0 nm,ε : 2.1〇xl04(濃度 1.59X10·5 mol/1) (4) 分解溫度(TG-DTA: 100 ml/分鐘氮氣流中,升溫l〇°C/ 分鐘) 2〇〇.5°C :熔點’ 284.7°C :質量減少開始點 [實施例8]化合物No. 24之合成 於經氮置換之反應燒瓶中,於冰浴下加入43.6 g(277 mmol)N,N-正二丁基甲醯胺以及13.3 g(87.1 mmol)填醢氣, 冰浴下攪拌1小時。於冰浴下添加12.2 g(58.0 mmol)5-溴-1-曱基吲哚,於100°C下攪拌4小時。冷卻至室温,餾去N,N-正二丁基曱酿胺後,添加58.0 g(315 mmol)六氟化構酸釺’ 進行均勻混合。添加1 L水於室溫下攪拌3 〇分鐘進行清洗 後,過濾分離析出物。自丙酮/曱醇混合溶劑進行再結晶, 經由過濾、乾燥’獲得18.9 g(收率65.8%)淡黃色固體。確 認所得之淡黃色固體為目標物之化合物N〇. 24 »以下表示 所得化合物No. 24之分析結果。 (1) H-NMR(ppm、DMSO溶劑) °-95(t ; 3H ; J=7.3Hz) ' 0.96(t ; 3H ; J = 7.3Hz) ' 1.36(tq ; 2H; J = 7.3'7.8Hz)' 1.5 0(tq; 2H; J = 7.6' 7.8Hz)' 1.72-1.87(m; ί 13344.doc •33· 1376369 4H)、3.91(t ; 4 Η ; J = 7.1Hz)、4.04(s ; 3H)、7.59(dd ; 1H ; J=1.7、8.8Hz)、7.7l(d; 1H; J=8.8Hz)' 8.41(ci; 1H; J=1.7Hz)、 8.58(s ; 1H) > 9.11(s ; 1H) (2) IR吸收(cm·1) 2964、1638、1530、1449、1353、1253、1123、838 (3) UV吸收測定(氯仿溶劑)
Xmax : 354.0 nm ’ ε : 2.14><104(濃度 l.OlxlO·5 mol") (4) 分解溫度(TG-DTA : 100 ml/分鐘氮氣流中,升溫1(TC/ 分鐘) 161.7°C :熔點,313.8°C :質量減少開始點 [實施例9]化合物No. 23之合成 將2.06 g(4.18 mmol)實施例8中獲得之化合物No. 24溶解 於20 ml丙酮中,滴加162 ml丙酮中溶解有5.0 mmol以化學 式[C]表示之陰離子之三乙基胺鹽者,加熱回流3小時。冷 卻至至k為止後’將反應物緩慢滴加至8 0 0 m 1水中,於室 溫下授拌14小時》過濾分離析出之固體,以丙酮清洗後, 使之乾燥而獲得4.1 8 g(收率93.7%)紅茶色固體。確認所得 之紅茶色固體為目標物之化合物Ν〇· 23。以下表示所得化 合物No. 23之分析結果。 (lVH-NMI^ppm、DMSO溶劑) 〇.95(t ; 6H ; J=7.1Hz) ' 1.01(t ; 12H ; J = 7.1Hz) > 1.36(tq ; 2H,J=7.3、7.3Hz)、1.48(tq;2H;J=7.3、7.3Hz)、1.72-1.85(m; 4H)、3.29(q ; 8H ; J=6.8Hz)、3.89(t; 4H ; J = 7.6Hz)、4.00(s ; 3H)、5.74(d ; 2H ; J=2.4Hz)、6.35(dd ; 2H ; J=2.7、9.5Hz)、 I13344.doc -34- 1376369 6.55(d; 2H; J=9.3Hz)、7.58(dd; 1H; J=1.7、8·8Ηζ)、7.64(d ; 2H ; J=9.3Hz)、7.69(d ; 1H ; J=8.8Hz)、7.84(dd ; 2H ; J=2.9、 9.3Hz)、8.39(d ; 1H ; J=1.7Hz)、8.54(s ; 1H)、9.00(d ; 2H ; J=2.9Hz) ' 9.08(s ; 1H) (2) IR吸收(cm·1) 2975 、 1611 、 1578 ' 1459 、 1320 、 1283 、 1262 、 1141 (3) UV吸收測定(氯仿溶劑)
Xmax : 357.5 nm,ε : 3·95χ104 541.5 mm,ε : 6·2〇χ104(濃度 2.18Χ10·6 mol") (4) 分解溫度(TG-DTA: 100 ml/分鐘氮氣流中,升溫i〇°c/ 分鐘) 2 16 · 8 C ·炫點’ 2 5 8.9 °C :質量減少開始點 [實施例10]含有黏著劑層之濾光器之製造 根據下述添加而製作UV清漆,於經過易密著處理之i88 μηι厚之PET薄膜上,藉由刮棒塗布機#9塗布該uv清漆後, 於100 C下乾燥10分鐘。其後,藉由附帶紅外線截止薄膜濾 光片之高壓水銀燈照射1 〇〇 mj紫外線,獲得於pET薄膜上具 有硬化膜厚約為5微米之薄膜層(黏著劑層)的濾光器。使用 曰本分光股份有限公司製造之紫外可見近紅外分光光度計 V-5 70測定該遽光器時,xmax為353 mm 〇 (添加) 化合物Nck4 ^ Λ 2·ϋ mg 丙烤酸系黏著劑(DB5541 ; DIA BOND公司製造)2〇 g 甲基乙基_ 113344.doc •35· 1376369 [實施例π]濾光器之製造 根據下述添加而製作UV清漆,於經過易密著處理之188 μιη厚之PET薄膜上,藉由刮棒塗布機塗布該旧清漆後, 於100。。下乾燥10分鐘。其後,藉由附帶紅外線截止薄膜濾 光片之高壓水銀燈照射10〇111】紫外線,獲得於pET薄膜上具 有硬化臈厚約為5微米之薄膜層的濾光器。使用日本分光股 份有限公司製造之紫外可見近紅外分光光度計v_ 5 7 〇測定 該渡光器時,Xmax為354 mm。 (添加) 100 g 樹脂成分80重量%)
Adecaopmer KRX-571-65 (旭電化工業公司製造之UV硬化樹脂
化合物N 〇. 5 曱基乙基酮 2.0 mg 60 g [實施例12 ]光學5己錄材料以及光學記錄媒體之製造暨光學 記錄媒體之評價
以化合物No. 4之濃度成為1·〇質量%之方式,將上述製造 例4中獲得之化合物]^0· 4溶解於2,2,3,3_四氟丙醇中,作為 2,2,3,3-四氟丙醇溶液而獲得光學記錄材料。於塗布鈦螯合 物(T-50 :日本曹達公司製造)進行水解,且設置有基礎層 (0.01 μπι)之直徑12 cm之聚碳酸醋碟基板上,藉由旋塗法塗 布上述光學把錄材料’形成厚度1〇〇 nm之光學記錄層而獲 付光學s己錄媒體。關於該光學記錄媒體,測定薄膜之吸收 UV光譜與入射角5。之反射光之UV光譜時,吸收Xmax為3 53 nm ’ 反射光 ^max為 382 nm。 113344.doc •36-
C S 1376369 可確認使用本發明之吲哚化合物之膜於特定波長 (340~390 nm)具有最大吸收(實施例10以及11),適合用作用 於濾光器之紫外線吸收劑。 又,具有藉由含有本發明之吲哚化合物之光學記錄材料 而形成之光學記錄層的光學記錄媒體,其於特定波長 (340~3 90 nm)具有反射光之最大吸收(實施例12)。以光碟為 代表之光學記錄媒體之再生模式中,關於使雷射光反射至 光學記錄媒體之反射光,可藉由雷射波長之光量差而檢測 有無記錄’故而較好的是於反射光之吸收光譜中,光學記 錄媒體越接近雷射光之波長處顯示越大之吸收強度。藉 此,含有本發明之吲哚化合物之本發明之光學記錄材料, 適合用作用於形成使用短波長雷射之光碟等使用405 nm雷 射光之光學記錄媒體的光學記錄層之光學記錄材料。 [評價例1-1〜1-5以及比較評價例丨·。以上述通式⑴表示之 化合物之耐光性評價 就實施例7〜9中獲得之化合物N〇. 21、No. 23以及No. 24 以及比較化合物1,進行耐光性評價。 首先,以成為1質量%之方式,於2,2,3,3_四氟丙醇中溶解 本發明之化合物,從而製備2,2,3,3_四氟丙醇溶液,藉由旋 塗法以2000 rpm、60秒之條件,將所得之溶液塗布於2〇χ2〇 mm之聚碳酸酯板上,製成試驗片。評價係藉由對該試驗片 照射55000勒克斯之光,分別照射24小時、150小時後,測 定照射前之UV吸收光譜之kmax下之吸光度殘存率而進 打。再者’[表1]中’作為併用物,以成為2,2,3,3·四氟丙醇 113344.doc •37- 1376369 溶液之0.1質量%之方式,溶解使用下述[化8]所示之 dimonium化合物或二硫醇化合物。[表1 ]中表示結果。 [表1] 化合物 吸光度殘存率(%) 24小時後 150小時後 評價例1-1 化合物No. 21 無 95.8 89.9 評價例1·2 化合物No. 23 無 97.2 91.6 評價例1-3 化合物No. 24 無 25.9 25.0 評價例1-4 化合物No. 24 二硫醇化合物 95.5 21.0 評價例1-5 化合物No. 24 dimonium化合物 92.2 3.9 比較評價例1-1 比較化合物No. 1 無 1.7 0
[化9] 比較化合物1
[化 10]
Dimonium化合物
自[表1]所明示,本發明之以上述通式(I)表示之化合物於 照射1 50小時後吸光度殘存率亦較高,併用dimonium化合物 或二硫醇化合物之情形時,照射150小時後,亦未發現吸光 -38- 113344.doc 1376369 度殘存率之降。另一方面,比較化合物於照射24小時後, 發現吸光度殘存率下降,又,照射ls〇小時後,發現吸光度 殘存率顯著下降。 產業上之可利用性 本發明係提供一種作為光學要素較好 物。又,使用該吲哚化合物之濾光器適厶之新穎吲哚化合 示裝置之濾光器,含有該吲11朵化合 。用作用於圖像顯 σ切而形成 料適用於形成光學記錄媒體之光學記錄層之光學記錄材
113344.doc -39-
Claims (1)
1376369 第095128767號專利申請案
(式中’ R以及R分別獨立表不氣原子、碳原子數1〜3 〇之 烴基或者以下述通式(II)表示之取代基,R3以及R4分別獨 立表不碳原子數1〜10之烷基、碳原子數卜⑺之烷氧基或 者碳原子數6〜3 0之芳基,R5、r6、R7以及R8分別獨立表 示氫原子、碳原子數1〜30之烴基、鹵素原子、羥基、硝 基、氰基、NHR或者NR’R",R、R’以及R"分別獨立表示 碳原子數1〜10之烷基,Rl以及R"亦可相互連接而形成 環,R5以及R6、R6以及r7、R7以及R8亦可分別相互連接 而形成碳環;AV表示q價之陰離子,q表示丨或2,p表示 將電荷保持為中性之係數); (式中R R分別獨立表示氫原子或者碳原子數丨〜4之烷 基,該院基中之亞甲基亦可以-0-或-C0-取代,Ζ表示直 接鍵結或者亦可具有取代基之碳原子數卜8之伸烧基,該 113344-1010316.doc 1376369 伸烷基中之亞甲基亦可以_〇_、_S_、_C0_、-COO-、_〇C〇-、 -S02-、-NH-、-CONH-、_NHCO_ ' _N=CH-或者 _CH=CH- 取代,M表示鐵、鈷、鎳)。 -- 2·如請求項1之濾光器’其中,上述通式⑴中,Ri為碳原子 _ 數1〜30之烴基’ R2為氫原子或者碳原子數丨〜%之烴基, R3為碳原子數1〜10之烷基,R4為碳原子數丨〜⑺之烷基。 3. 如請求項1或2之濾光器,其用於圖像顯示裝置。 4, 一種光學記錄材料,其係含有以下述通式(I)表示之吲哚 化合物而成者,係用於基體上形成有光學記錄層之光學 φ 記錄媒體的該光學記錄層:
(式中,R1以及R2分別獨立表示氫原子、碳原子數卜3〇 烴基或者以下述通式(11)表示之取代基,R3以及Μ分別 立表示碳原子數1〜10之烷基、碳原子數丨〜1〇之烷氧基 者碳原子數6〜3 0之芳基’ R5、r6、r7以及r8分別獨: 示氫原子、碳原子數1〜30之烴基 '函素原子、羥基、 基、氰基、NHR或者NR,R",R、R,以及R.,分別^表 碳原子數i〜10之烷基’ R,以及R"亦可相互連接而形 環,V以及“以及R'R7以及可分別相互連, 而形^碳環表示q價之陰離子,q表示p表 將電荷保持為中性之係數); 113344-1010316.doc S (II)1376369
(式中,Ra〜R1分別獨立表示氫原子或者碳原子數卜4之烷 基,該烷基中之亞甲基亦可以_〇或_c〇_取代,z表示直 接鍵結或者亦可具有取代基之碳原子數卜8之伸烷基,該 伸烷基中之亞甲基亦可以_〇_、S、、 S〇2- ' -NH- 、-CONH-、-NHCO-、·ν=(:Η-或者-CH=CH- 取代’ M表示鐵、結、鎳)。 5·如請求項4之光學記錄材料,其中’上述通式⑴中,&丨為 碳原子數卜30之烴基,r2為氫原子或者碳原子數丨〜”之 烴基,R3為碳原子數〗〜!〇之烷基,R4為碳原子數1〜之 院基0
113344-1010316.doc
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BE513714A (zh) | 1951-08-23 | 1900-01-01 | ||
IT557307A (zh) | 1955-02-23 | 1900-01-01 | ||
US2941898A (en) | 1957-12-16 | 1960-06-21 | Ilford Ltd | Production of multilayer photographic materials |
GB1159598A (en) | 1965-10-28 | 1969-07-30 | Fuji Photo Film Co Ltd | Multiple Coating Process and Apparatus |
US3508947A (en) | 1968-06-03 | 1970-04-28 | Eastman Kodak Co | Method for simultaneously applying a plurality of coated layers by forming a stable multilayer free-falling vertical curtain |
US6558768B2 (en) * | 2000-03-07 | 2003-05-06 | Ricoh Company, Ltd. | Optical recording medium and optical recording and reading method using the same |
JP4183918B2 (ja) * | 2001-02-14 | 2008-11-19 | 株式会社リコー | 光記録媒体及びこれを用いる光記録方法 |
JP4145529B2 (ja) | 2002-02-15 | 2008-09-03 | 三菱化学株式会社 | 光学記録媒体及び記録方法 |
TW589349B (en) * | 2002-04-19 | 2004-06-01 | Ind Tech Res Inst | New indolestyryl compounds and its use for a high density optical recording medium |
JP2004102223A (ja) * | 2002-07-15 | 2004-04-02 | Fuji Photo Film Co Ltd | 有機elディスプレイ素子用フィルター |
JP2004058365A (ja) | 2002-07-26 | 2004-02-26 | Matsushita Electric Ind Co Ltd | 光記録媒体および製造方法 |
JP2004174838A (ja) | 2002-11-26 | 2004-06-24 | Fuji Photo Film Co Ltd | 光情報記録媒体および情報記録方法 |
JP2004209771A (ja) * | 2002-12-27 | 2004-07-29 | Fuji Photo Film Co Ltd | 光情報記録媒体 |
-
2006
- 2006-07-19 KR KR1020087002962A patent/KR101354109B1/ko not_active IP Right Cessation
- 2006-07-19 EP EP06781236A patent/EP1921063B1/en not_active Expired - Fee Related
- 2006-07-19 WO PCT/JP2006/314229 patent/WO2007018015A1/ja active Application Filing
- 2006-07-19 CN CN2006800292395A patent/CN101238100B/zh not_active Expired - Fee Related
- 2006-07-19 DE DE602006016619T patent/DE602006016619D1/de active Active
- 2006-07-19 US US11/996,502 patent/US7923091B2/en not_active Expired - Fee Related
- 2006-07-19 JP JP2007529470A patent/JP5046936B2/ja not_active Expired - Fee Related
- 2006-08-04 TW TW095128767A patent/TW200720251A/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP1921063A1 (en) | 2008-05-14 |
EP1921063B1 (en) | 2010-09-01 |
JP5046936B2 (ja) | 2012-10-10 |
JPWO2007018015A1 (ja) | 2009-02-19 |
US7923091B2 (en) | 2011-04-12 |
CN101238100A (zh) | 2008-08-06 |
EP1921063A4 (en) | 2009-07-15 |
US20090092782A1 (en) | 2009-04-09 |
CN101238100B (zh) | 2011-06-22 |
KR20080042810A (ko) | 2008-05-15 |
KR101354109B1 (ko) | 2014-01-22 |
TW200720251A (en) | 2007-06-01 |
DE602006016619D1 (de) | 2010-10-14 |
WO2007018015A1 (ja) | 2007-02-15 |
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