JPWO2007018015A1 - インドール化合物、光学フィルター及び光学記録材料 - Google Patents
インドール化合物、光学フィルター及び光学記録材料 Download PDFInfo
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- JPWO2007018015A1 JPWO2007018015A1 JP2007529470A JP2007529470A JPWO2007018015A1 JP WO2007018015 A1 JPWO2007018015 A1 JP WO2007018015A1 JP 2007529470 A JP2007529470 A JP 2007529470A JP 2007529470 A JP2007529470 A JP 2007529470A JP WO2007018015 A1 JPWO2007018015 A1 JP WO2007018015A1
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- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- WRKCIHRWQZQBOL-UHFFFAOYSA-N phosphoric Acid Monooctyl Ester Natural products CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- GLGXXYFYZWQGEL-UHFFFAOYSA-M potassium;trifluoromethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)F GLGXXYFYZWQGEL-UHFFFAOYSA-M 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000005507 spraying Methods 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
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 238000002834 transmittance Methods 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 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
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—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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- G11B7/24—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
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- 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
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- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
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- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
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- 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
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- 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
- G11B7/248—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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- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
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- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
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- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
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- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
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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)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Abstract
(式中、R1及びR2はそれぞれ独立に、水素原子、炭素原子数1〜30の炭化水素基又は下記一般式(II)で表される置換基を表し、R3及びR4はそれぞれ独立に、炭素原子数1〜10のアルキル基、炭素原子数1〜10のアルコキシ基又は炭素原子数6〜30のアリール基を表し、R5、R6、R7及びR8はそれぞれ独立に、水素原子、炭素原子数1〜30の炭化水素基、ハロゲン原子、水酸基、ニトロ基、シアノ基、NHR又はNR’R’’を表し、R、R’及びR’’はそれぞれ独立に、炭素原子数1〜10のアルキル基を表し、R’及びR’’は互いに連結して環を形成していてもよく、R5及びR6、R6及びR7、R7及びR8はそれぞれ、互いに連結して環を形成していてもよい。Anq-はq価のアニオンを表し、qは1又は2を表し、pは電荷を中性に保つ係数を表す。)
Description
上記一般式(I)で表される本発明のインドール化合物において、R1、R2、R5、R6、R7及びR8で表される炭素原子数1〜30の炭化水素基としては、メチル、エチル、プロピル、イソプロピル、ブチル、第二ブチル、第三ブチル、イソブチル、アミル、イソアミル、第三アミル、ヘキシル、シクロヘキシル、シクロヘキシルメチル、2−シクロヘキシルエチル、ヘプチル、イソヘプチル、第三ヘプチル、n−オクチル、イソオクチル、第三オクチル、2−エチルヘキシル、ノニル、イソノニル、デシル、ドデシル、トリデシル、テトラデシル、ペンタデシル、ヘキサデシル、ペプタデシル、オクタデシル等のアルキル基、ビニル、1−メチルエテニル、2−メチルエテニル、プロペニル、ブテニル、イソブテニル、ペンテニル、ヘキセニル、ヘプテニル、オクテニル、デセニル、ぺンタデセニル、1−フェニルプロペン−3−イル等のアルケニル基、フェニル、ナフチル、2−メチルフェニル、3−メチルフェニル、4−メチルフェニル、4−ビニルフェニル、3−イソプロピルフェニル、4−イソプロピルフェニル、4−ブチルフェニル、4−イソブチルフェニル、4−第三ブチルフェニル、4−ヘキシルフェニル、4−シクロヘキシルフェニル、4−オクチルフェニル、4−(2−エチルヘキシル)フェニル、4−ステアリルフェニル、2,3−ジメチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2,4−ジ第三ブチルフェニル、シクロヘキシルフェニル等のアルキルアリール基、ベンジル、フェネチル、2−フェニルプロパン−2−イル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル等のアリールアルキル基等、これらがエーテル結合及び/又はチオエーテル結合で中断されたもの、例えば、2−メトキシエチル、3−メトキシプロピル、4−メトキシブチル、2−ブトキシエチル、メトキシエトキシエチル、メトキシエトキシエトキシエチル、3−メトキシブチル、2−フェノキシエチル、3−フェノキシプロピル、2−メチルチオエチル、2−フェニルチオエチル等が挙げられる。更に、これらの基は、アルコキシ基、アルケニル基、ニトロ基、シアノ基、ハロゲン原子等で置換されていてもよく、アルコキシ基、アルケニル基及びシアノ基から選択される1種以上で置換される場合は、これらの置換基を含めた全体の炭素原子数が最大で30である。
また、本発明のインドール化合物は、光学要素の他に、医薬品、農薬、香料、染料等の合成中間体、あるいは各種機能性材料等に用いることもできる。
本発明の光学フィルターは、本発明のインドール化合物を含有する。本発明のインドール化合物は、吸収極大波長を340〜390nmに持ち、410nm以下の紫外線及び一部の可視光線を吸収して遮断することができるので、本発明のインドール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である。本発明の光学フィルターは、画像表示装置用の他に、分析装置用、半導体装置製造用、天文観測用、光通信用、眼鏡レンズ用等の各種用途にも用いることができる。
本発明のインドール化合物及び任意成分を本発明の光学フィルターに含有させる方法として、上述の(1)〜(4)のいずれの方法を採る場合も、各成分の配合割合は、上述の配合割合に準じればよい。
本発明の光学記録材料は、本発明のインドール化合物を含有し、光学記録媒体の光学記録層の形成に用いられるものであり、含有するインドール化合物の光吸収特性に応じて各種の光学記録媒体に適用することができる。本発明の光学記録材料の中でも、波長が380nm〜420nmの短波長レーザ用の光ディスクに特に適合するのは、含有するインドール化合物が、溶液状態での光吸収特性において、最大吸収波長λmaxを320〜420nmの範囲に有するものである。また、吸収強度については、λmaxでのεが1.0×104より小さいと記録感度が低下するおそれがあるので、1.0×104以上が好ましい。上記インドール化合物の溶液状態でのλmax及びεの測定は、常法に従って、試料溶液の濃度、測定に用いる溶媒等を選択して行なうことができる。
窒素置換した反応フラスコに、ジメチルホルムアミド(DMF)10ml及びクロロホルム80mlを仕込み、氷冷下でオキシ塩化リン6.91g(45.1mmol)を滴下し、氷冷下で1時間攪拌した。1−メチルインドール3.94g(30.0mmol)をクロロホルム40mlに溶解したものを氷冷下で滴下し、3時間加熱還流した。室温に冷却し、反応液を六フッ化リン酸カリウム23.1g(126mmol)の400ml水溶液に徐々に滴下し、室温で2時間撹拌した。析出物をろ別し、メタノール200mlを用いて室温で30分間撹拌し、洗浄を行なった。ろ過、乾燥を経て、桃色固体を9.32g(収率93.4%)得た。得られた桃色個体は、目的物である化合物No.1であることが確認された。得られた化合物No.1についての分析結果を以下に示す。
3.57(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吸収(cm-1)
3168、1647、1536、1466、1402、1349、1256、1113、838、758
(3)UV吸収測定(アセトン溶媒)
λmax;345.0nm、ε;1.86×104(濃度6.68×10-6mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
295.8℃;融点、326.7℃;質量減少開始点
窒素置換した反応フラスコに、DMF10ml及びクロロホルム80mlを仕込み、氷冷下でオキシ塩化リン6.90g(45.0mmol)を滴下し、氷冷下で1時間攪拌した。1−メチル−2−フェニルインドール6.22g(30.0mmol)をクロロホルム40mlに溶解したものを氷冷下で滴下し、3時間加熱還流した。室温に冷却し、反応液を六フッ化リン酸カリウム20.0g(109mmol)の400ml水溶液に徐々に滴下し、室温で30分間撹拌した。水層を除去し、水400mlを加えて室温で30分間撹拌後、析出物をろ別し、メタノール150mlを用いて室温で30分間撹拌し、洗浄を行なった。ろ過、乾燥を経て、灰白色固体を得た。アセトニトリル/エタノール混合溶媒から再結晶を行い、灰白色固体を5.06g(収率41.5%)得た。得られた灰白色固体は、目的物である化合物No.2であることが確認された。得られた化合物No.2についての分析結果を以下に示す。
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吸収(cm-1)
3430、1656、1490、1474、1463、1391、1120、842、795、754、705
(3)UV吸収測定(アセトン溶媒)
λmax;348.5nm、ε;1.74×104(濃度1.93×10-6mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
162.6℃;融点、332.9℃;質量減少開始点
窒素置換した反応フラスコに、氷冷下でN,N−n−ジブチルホルムアミド15g(95.4mmol)及びオキシ塩化リン5.21g(34.0mmol)を仕込み、氷冷下で1時間攪拌した。1−メチルインドール2.62g(20.0mmol)を氷冷下で加え、100℃で3時間撹拌した。室温に冷却し、N,N−n−ジブチルホルムアミドを留去後、六フッ化リン酸カリウム15.3g(95.4mmol)を加えて均一に混合した。水150mlを加えて室温で30分間撹拌後、析出物をろ別し、メタノール100mlを用いて室温で30分間撹拌し、更に水50mlを加え、室温で30分間撹拌して洗浄を行なった。ろ過、乾燥を経て、黄土色固体を得た。アセトニトリル/メタノール混合溶媒から再結晶を行い、ろ過、乾燥を経て、薄桃色固体を2.90g(収率34.8%)得た。得られた薄桃色固体は、目的物である化合物No.3であることが確認された。得られた化合物No.3についての分析結果を以下に示す。
0.96(t;3H;J=7.3Hz)、0.97(t;3H;J=7.3Hz)、1.36(tq;2H;J=7.6、7.3Hz)、1.52(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吸収(cm-1)
2955、2874、1639、1532、1476、1352、1256、1114、834、751
(3)UV吸収測定(クロロホルム溶媒)
λmax;357.0nm、ε;2.04×104(濃度5.64×10-6mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
179.7℃;融点、307.8℃;質量減少開始点
窒素置換した反応フラスコに、氷冷下でN,N−n−ジブチルホルムアミド15g(95.4mmol)及びオキシ塩化リン5.21g(34.0mmol)を仕込み、氷冷下で1時間攪拌した。1−メチルインドール6.22g(30.0mmol)を氷冷下で加え、100℃で4時間撹拌した。室温に冷却し、N,N−n−ジブチルホルムアミドを留去後、トリフルオロメタンスルホン酸カリウム25.0g(132mmol)を加えて均一に混合した。水150mlを加えて室温で30分間超音波照射を行なった後、析出物をろ別した。エタノール/ジエチルエーテル混合溶媒から再結晶を行い、ろ過、乾燥を経て、薄黄色固体を4.64g(収率55.1%)得た。得られた薄黄色固体は、目的物である化合物No.4であることが確認された。得られた化合物No.4についての分析結果を以下にしめす。
0.94(t;3H;J=6.6Hz)、0.96(t;3H;J=7.1Hz)、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)、7.35−7.50(m;2H)、7.65−7.80(m;1H)、8.05−8.20(m;1H)、8.58(s;1H)、9.09(s;1H)
(2)IR吸収(cm-1)
2960、2874、1624、1588、1476、1464、1430、1265、1153、1032、965
(3)UV吸収測定(クロロホルム溶媒)
λmax;356.5nm、ε;1.84×104(濃度9.89×10-6mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
110.3℃;融点、287.1℃;質量減少開始点
窒素置換した反応フラスコに、氷冷下でN,N−n−ジブチルホルムアミド22.5g(143mmol)及びオキシ塩化リン7.82g(51.0mmol)を仕込み、氷冷下で1時間攪拌した。1−(3,5−ビストリフルオロメチルフェニル)インドール6.08g(18.4mmol)を氷冷下で加え、100℃で4時間撹拌した。室温に冷却し、N,N−n−ジブチルホルムアミドを留去後、六フッ化リン酸カリウム50.0g(272mmol)を加えて均一に混合した。水1Lを加えて室温で30分間撹拌後、水層を除去してエタノール1Lを用いて30分間撹拌して洗浄を行なった後、析出物をろ別した。アセトン/エタノール混合溶媒から再結晶を行い、ろ過、乾燥を経て、無色透明針状結晶を2.75g(収率24.3%)得た。得られた無色透明針状結晶は、目的物である化合物No.5であることが確認された。得られた化合物No.5についての分析結果を以下に示す。
0.96(t;3H;J=7.6Hz)、0.99(t;3H;J=7.1Hz)、1.40(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;2H;J=7.6Hz)、4.11(t;2H;J=7.8Hz)、7.51(dd;1H;J=8.5、7.1Hz)、7.55(dd;1H;J=7.8、7.1Hz)、7.64(d;1H;J=8.3Hz)、8.26(d;1H;J=7.6Hz)、8.41(s;1H)、8.60(s;2H)、8.83(s;1H)、9.34(s;1H)
(2)IR吸収(cm-1)
2967、2880、1646、1522、1475、1360、1282、1230、1192、1146、843、825、762
(3)UV吸収測定(クロロホルム溶媒)
λmax;354.5nm、ε;1.92×104(濃度6.87×10-6mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
183.3℃;融点、297.5℃;質量減少開始点
窒素置換した反応フラスコに、氷冷下でN,N−n−ジブチルホルムアミド22.5g(143mmol)及びオキシ塩化リン7.82g(51.0mmol)を仕込み、氷冷下で1時間攪拌した。1−メチル−2−フェニルインドール6.22g(30.0mmol)を氷冷下で加え、100℃で4時間撹拌した。室温に冷却し、N,N−n−ジブチルホルムアミドを留去後、六フッ化リン酸カリウム50.0g(272mmol)を加えて均一に混合した。水1Lを加えて室温で30分間撹拌して洗浄を行なった後、析出物をろ別した。アセトン/エタノール混合溶媒から再結晶を行い、ろ過、乾燥を経て、薄緑色固体を3.02g(収率20.4%)得た。得られた薄緑色固体は、目的物である化合物No.6であることが確認された。得られた化合物No.6についての分析結果を以下に示す。
0.80(t;3H;J=7.3Hz)、0.90(t;3H;J=7.3Hz)、1.20(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;J=6.8Hz)、7.49(dd;1H;J=7.2、7.2Hz)、7.53(dd;1H;J=7.1、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吸収(cm-1)
2960、2935、2874、1651、1477、1464、1404、1368、1086、838、802、750
(3)UV吸収測定(クロロホルム溶媒)
λmax;352.5nm、ε;2.48×104(濃度4.07×10-6mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
100.4℃;融点、304.9℃;質量減少開始点
窒素置換した反応フラスコに、氷冷下でN,N−n−ジメチルホルムアミド10ml、クロロホルム80ml及びオキシ塩化リン6.74g(44.0mmol)を仕込み、氷冷下で1時間攪拌した。1−プロピルフェロセニルインドール10.5g(29.3mmol)のクロロホルム40ml溶液を氷冷下で加え、3.5時間加熱還流した。室温に冷却し、六フッ化リン酸カリウム23.5g(127mmol)の水500ml水溶液に徐々に滴下し、室温で1時間撹拌した。析出物をろ別し、乾燥を経て、茶色固体を16.2g(収率99.4%)得た。得られた茶色固体は、目的物である化合物No.21であることが確認された。得られた化合物No.21についての分析結果を以下に示す。
1.48(dt;2H;J=7.3、7.3Hz)、1.90(dt;2H;J=7.3、7.3Hz)、2.32(t;2H;J=7.6Hz)、3.61(s;3H)、3.74(s;3H)、4.03(s;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吸収(cm-1)
1654、1530、1404、1364、1105、836
(3)UV吸収測定(クロロホルム溶媒)
λmax;353.0nm、ε;2.10×104(濃度1.59×10-5mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
200.5℃;融点、284.7℃;質量減少開始点
窒素置換した反応フラスコに、氷冷下でN,N−n−ジブチルホルムアミド43.6g(277mmol)及びオキシ塩化リン13.3g(87.1mmol)を仕込み、氷冷下で1時間攪拌した。5−ブロモ−1−メチルインドール12.2g(58.0mmol)を氷冷下で加え、100℃で4時間撹拌した。室温に冷却し、N,N−n−ジブチルホルムアミドを留去後、六フッ化リン酸カリウム58.0g(315mmol)を加えて均一に混合した。水1Lを加えて室温で30分間撹拌して洗浄を行なった後、析出物をろ別した。アセトン/メタノール混合溶媒から再結晶を行い、ろ過、乾燥を経て、薄黄色固体を18.9g(収率65.8%)得た。得られた薄黄色固体は、目的物である化合物No.24であることが確認された。得られた化合物No.24についての分析結果を以下に示す。
0.95(t;3H;J=7.3Hz)、0.96(t;3H;J=7.3Hz)、1.36(tq;2H;J=7.3、7.8Hz)、1.50(tq;2H;J=7.6、7.8Hz)、1.72−1.87(m;4H)、3.91(t;4H;J=7.1Hz)、4.04(s;3H)、7.59(dd;1H;J=1.7、8.8Hz)、7.71(d;1H;J=8.8Hz)、8.41(d;1H;J=1.7Hz)、8.58(s;1H)、9.11(s;1H)
(2)IR吸収(cm-1)
2964、1638、1530、1449、1353、1253、1123、838
(3)UV吸収測定(クロロホルム溶媒)
λmax;354.0nm、ε;2.14×104(濃度1.01×10-5mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
161.7℃;融点、313.8℃;質量減少開始点
実施例8で得られた化合物No.24の2.06g(4.18mmol)をアセトン20mlに溶解し、化学式〔C〕で示されるアニオンのトリエチルアミン塩5.0mmolをアセトン162mlに溶解したものを滴下して、3時間加熱還流した。室温まで冷却後、反応物を水800mlに徐々に滴下し、室温で14時間撹拌した。析出した固体をろ別し、アセトンで洗浄後、乾燥させて赤茶色固体を4.18g(収率93.7%)得た。得られた赤茶色固体は、目的物である化合物No.23であることが確認された。得られた化合物No.23についての分析結果を以下に示す。
0.95(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)、6.55(d;2H;J=9.3Hz)、7.58(dd;1H;J=1.7、8.8Hz)、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吸収(cm-1)
2975、1611、1578、1459、1320、1283、1262、1141
(3)UV吸収測定(クロロホルム溶媒)
λmax;357.5nm、ε;3.95×104
541.5nm、ε;6.20×104(濃度2.18×10-6mol/l)
(4)分解温度(TG−DTA:100ml/分窒素気流中、昇温10℃/分)
216.8℃;融点、258.9℃;質量減少開始点
下記の配合にてUVワニスを作成し、易密着処理した188μm厚のPET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、100℃で10分間乾燥させた。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、PETフィルム上に硬化膜厚約5ミクロンのフィルム層(粘着剤層)を有する光学フィルターを得た。この光学フィルターを日本分光(株)製紫外可視近赤外分光光度計V−570で測定したところ、λmaxが353nmであった。
化合物No.4 2.0mg
アクリル系粘着剤(DB5541:ダイヤボンド社製) 20g
メチルエチルケトン 80g
下記の配合にてUVワニスを作成し、易密着処理した188μm厚のPET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、100℃で10分間乾燥させた。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、PETフィルムに硬化膜厚約5ミクロンのフィルム層を有する光学フィルターを得た。この光学フィルターを日本分光(株)製紫外可視近赤外分光光度計V−570で測定したところ、λmaxが354nmであった。
アデカオプトマーKRX−571−65 100g
(旭電化工業社製UV硬化樹脂、樹脂分80重量%)
化合物No.5 2.0mg
メチルエチルケトン 60g
上記製造例4で得た化合物No.4を、化合物No.4の濃度が1.0質量%となるように2,2,3,3−テトラフルオロプロパノールに溶解して、2,2,3,3−テトラフルオロプロパノール溶液として光学記録材料を得た。チタンキレート化合物(T−50:日本曹達社製)を塗布、加水分解して下地層(0.01μm)を設けた直径12cmのポリカーボネートディスク基板上に、上記の光学記録材料をスピンコーティング法にて塗布して、厚さ100nmの光学記録層を形成し光学記録媒体を得た。この光学記録媒体について、薄膜の吸収UVスペクトルと入射角5°の反射光のUVスペクトルを測定したところ、吸収λmaxは353nm、反射光λmaxは382nmであった。
また、本発明のインドール化合物を含有する光学記録材料により形成された光学記録層を有する光学記録媒体は、特定の波長(340〜390nm)に反射光の吸収極大を有している(実施例12)。光ディスクに代表される光学記録媒体の再生モードでは、レーザ光を光学記録媒体に反射させた反射光について、レーザ波長の光量の差で記録の有無を検出するので、光学記録媒体は、反射光の吸収スペクトルにおいて、レーザ光の波長に近いところで大きい吸収強度を示すものほど好ましい。よって、本発明のインドール化合物を含有する本発明の光学記録材料は、短波長レーザ用光ディスク等の405nmのレーザ光を用いる光学記録媒体の光学記録層の形成に用いる光学記録材料として好適である。
実施例7〜9で得られた化合物No.21、No.23及びNo.24及び比較化合物1について、耐光性評価を行なった。
まず、2,2,3,3−テトラフルオロプロパノールに本発明の化合物を、1質量%となるように溶解して2,2,3,3−テトラフルオロプロパノール溶液を調製し、得られた溶液を、20×20mmのポリカーボネート板上に2000rpm、60秒でスピンコーティング法により塗布して、試験片を作成した。評価は、該試験片に55000ルクスの光を照射し、それぞれ24時間、150時間照射した後、照射前のUV吸収スペクトルのλmaxでの吸光度残存率を測定することにより行なった。尚、〔表1〕において、併用物としては、下記[化8]に示すジイモニウム化合物又はジチオール化合物を、2,2,3,3−テトラフルオロプロパノール溶液の0.1質量%となるように溶解して用いた。結果を〔表1〕に示す。
Claims (5)
- 下記一般式(I)で表されるインドール化合物。
- 上記一般式(I)において、R1が炭素原子数1〜30の炭化水素基であり、R2が水素原子又は炭素原子数1〜30の炭化水素基であり、R3が炭素原子数1〜10のアルキル基であり、R4が炭素原子数1〜10のアルキル基である請求の範囲第1項に記載のインドール化合物。
- 請求の範囲第1又は2項に記載のインドール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3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又は2項に記載のインドール化合物を含有してなる光学記録材料。
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US20090092782A1 (en) | 2009-04-09 |
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TWI376369B (ja) | 2012-11-11 |
KR20080042810A (ko) | 2008-05-15 |
DE602006016619D1 (de) | 2010-10-14 |
US7923091B2 (en) | 2011-04-12 |
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