JP4688480B2 - シアニン化合物、該化合物を用いた光学記録材料、及び光学記録媒体 - Google Patents
シアニン化合物、該化合物を用いた光学記録材料、及び光学記録媒体 Download PDFInfo
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- JP4688480B2 JP4688480B2 JP2004340485A JP2004340485A JP4688480B2 JP 4688480 B2 JP4688480 B2 JP 4688480B2 JP 2004340485 A JP2004340485 A JP 2004340485A JP 2004340485 A JP2004340485 A JP 2004340485A JP 4688480 B2 JP4688480 B2 JP 4688480B2
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- cyanine compound
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
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- 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
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- 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
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- 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
- G11B7/2467—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 azo-dyes
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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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- 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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- 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
- G11B7/249—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 organometallic compounds
- G11B7/2495—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 organometallic compounds as anions
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- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- 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
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
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- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
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- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- 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
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
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- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- 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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- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
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- G11B7/2535—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polyesters, e.g. PET, PETG or PEN
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- 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
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/256—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers improving adhesion between layers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/146—Laser beam
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
しかしながら、従来のシアニン系化合物は、熱分解特性に問題がある。高速記録がなされる光学記録媒体の記録要素としては、分解温度が低いものが適合するが、報告されている上記のシアニン系化合物は、この点で充分な特性を有しているものではなかった。
また、本発明は、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、上記シアニン化合物を含有してなる光学記録材料を提供するものである。
また、本発明は、基体上に、上記光学記録材料からなる薄膜を形成した光学記録媒体を提供するものである。
これらの各種化合物は、上記光学記録層において好ましくは0〜50質量%の範囲で使用される。そのためには、本発明の光学記録材料において、これらの各種化合物の含有量は、本発明の光学記録材料に含まれる固形分基準で0〜50質量%とするのが好ましい。
反応フラスコに、下記〔化8〕に示すインドール誘導体A2.9g(0.005mol)、下記〔化9〕に示す合成ルートから得られた中間体B2.0g(0.005mol)、及びピリジン4.2g(0.05mol)を仕込み、40℃に昇温し、均一になるように攪拌した。無水酢酸0.8g(0.0075mol)を滴下して4時間反応させた。冷却の後、クロロホルム40g/水30gで洗浄を2回行い、次いで、六フッ化リンカリウム3g(0.015mol)水溶液で2回塩交換を行った後、水洗を2回行った。エバポレーターにて脱溶媒した後、メタノール35gにて晶析を行った。ろ過、メタノール洗浄、真空乾燥により、灰色固体2.6g(収率 74%)を得た。得られた灰色固体は、分析の結果、目的物(化合物No.2の六フッ化リン塩)であることが確認された。分析結果を以下に示す。
・光学特性(クロロホルム、1.01×10-6モル/リットル)
λmax;584nm、ε;1.2×105
・吸熱温度(窒素中にて10℃/分の昇温条件でのTG/DTA測定による吸熱ピークトップ)
213.1℃
・分子量(TOF−マススペクトル分析)
660.7
・1H−NMR(溶媒;DMSO)
図1に1H−NMRスペクトルを示す。
反応フラスコに、上記インドール誘導体A16.5g、下記〔化10〕に示す中間体C8.7g(0.03mol)、及びピリジン47.4g(0.6mol)を仕込み攪拌した。室温にて無水酢酸4.6g(0.045mol)を滴下して、15時間反応させた。クロロホルム150g/水100gで洗浄を2回行った後、六フッ化リンカリウム5.5g(0.03mol)水溶液で塩交換を1回行ない、次いで水洗を2回行った。エバポレーターにて脱溶媒してクルード体を得た。得られたクルード体をカラム精製し(酢酸エチル:ヘキサン=1.5:1、原点メタノール抽出)、濃縮により紫色固体1.8gを得た。更に、ジメチルアセトアミド/メタノールにより再晶析を行い、紫色固体1.3g(収率7%)を得た。得られた紫色固体は、分析の結果、目的物(化合物No.8の六フッ化リン塩)であることが確認された。分析結果を以下に示す。
・光学特性(クロロホルム、9.81×10-6モル/リットル)
λmax;547nm、ε;1.14×105
・吸熱温度(窒素中にて10℃/分の昇温条件でのTG/DTA測定による吸熱ピークトップ)
218.4℃
・分子量(TOF−マススペクトル分析)
616.6
・1H−NMR(溶媒;DMSO)
図2に1H−NMRスペクトルを示す。
上記実施例で得た化合物No.2及び8並びに以下の〔化11〕に示す比較化合物1について、窒素気流中での示差熱分析を行い、熱分解温度を測定した。熱分解温度は、窒素中にて10℃/分の昇温条件によるDTAの発熱ピークトップの温度とした。結果を表1に示す。
化合物No.2の六フッ化リン塩を、2,2,3,3−テトラフルオロプロパノールに濃度1質量%となるように溶解して、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)を塗布した後、加水分解して下地層(0.01μ)を設けた直径12cmのポリカーボネートディスク基板上に、上記光学記録材料をスピンコーティング法にて塗布し(回転数2000rpmで1分間の回転塗布)、光学記録媒体を得た。この光学記録媒体について、透過光UVスペクトルの測定を行ったところ、λmaxは598nmであり、上記光学記録材料は、DVD−R用の光学記録材料として適するものであることが確認できた。
化合物No.2の六フッ化リン塩に代えて化合物No.8の六フッ化リン塩を用いた以外は、実施例3と同様にして、光学記録材料を作製し、該光学記録材料を用いて光学記録媒体を得た。この光学記録媒体について、透過光UVスペクトルの測定を行ったところ、λmaxは558nmであり、上記光学記録材料は、DVD−R用の光学記録材料として適するものであることが確認できた。
Claims (9)
- 下記一般式(I)で表されるシアニン化合物。
- 上記一般式(I)における環Bがベンゼン環である請求項1記載のシアニン化合物。
- 上記一般式(I)におけるXがSである請求項1又は2記載のシアニン化合物。
- 上記一般式(I)におけるXがOである請求項1又は2記載のシアニン化合物。
- 上記一般式(I)における環Aがナフタレン環である請求項1〜4のいずれか一項に記載のシアニン化合物。
- 上記一般式(I)におけるY1及びY2が炭素原子数1〜8のアルキル基である請求項1〜5のいずれか一項に記載のシアニン化合物。
- 上記一般式(I)におけるR1及びR2のいずれかがメチル基である請求項1〜6のいずれか一項に記載のシアニン化合物。
- 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、請求項1〜7のいずれか一項に記載のシアニン化合物を含有してなる光学記録材料。
- 基体上に、請求項8記載の光学記録材料からなる薄膜を形成した光学記録媒体。
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004340485A JP4688480B2 (ja) | 2004-11-25 | 2004-11-25 | シアニン化合物、該化合物を用いた光学記録材料、及び光学記録媒体 |
CN201210063842.2A CN102675304B (zh) | 2004-11-25 | 2005-10-13 | 花青化合物、使用该化合物的光学记录材料和光学记录介质 |
PCT/JP2005/018852 WO2006057113A1 (ja) | 2004-11-25 | 2005-10-13 | シアニン化合物、該化合物を用いた光学記録材料、及び光学記録媒体 |
EP05793651.0A EP1826208B1 (en) | 2004-11-25 | 2005-10-13 | Cyanine compound, optical recording material utilizing the compound, and optical recording medium |
CNA2005800386858A CN101056874A (zh) | 2004-11-25 | 2005-10-13 | 花青化合物、使用该化合物的光学记录材料和光学记录介质 |
KR1020077010936A KR101272743B1 (ko) | 2004-11-25 | 2005-10-13 | 시아닌 화합물, 이 화합물을 이용한 광학기록재료, 및광학기록매체 |
US11/791,487 US7682773B2 (en) | 2004-11-25 | 2005-10-13 | Cyanine compound, optical recording material using the same and optical recording medium |
TW094137388A TWI419936B (zh) | 2004-11-25 | 2005-10-25 | A cyanine compound, an optical recording material using the compound, and an optical recording medium |
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JP2004340485A JP4688480B2 (ja) | 2004-11-25 | 2004-11-25 | シアニン化合物、該化合物を用いた光学記録材料、及び光学記録媒体 |
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JP2006151823A JP2006151823A (ja) | 2006-06-15 |
JP4688480B2 true JP4688480B2 (ja) | 2011-05-25 |
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JP2004340485A Expired - Fee Related JP4688480B2 (ja) | 2004-11-25 | 2004-11-25 | シアニン化合物、該化合物を用いた光学記録材料、及び光学記録媒体 |
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US (1) | US7682773B2 (ja) |
EP (1) | EP1826208B1 (ja) |
JP (1) | JP4688480B2 (ja) |
KR (1) | KR101272743B1 (ja) |
CN (2) | CN101056874A (ja) |
TW (1) | TWI419936B (ja) |
WO (1) | WO2006057113A1 (ja) |
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JP2006305920A (ja) * | 2005-04-28 | 2006-11-09 | Tdk Corp | 光記録材料、光記録材料溶液並びに光記録媒体及びその製造方法 |
JP2007196661A (ja) * | 2005-12-27 | 2007-08-09 | Mitsubishi Kagaku Media Co Ltd | 光学記録媒体及びアザシアニン色素 |
JP4953645B2 (ja) * | 2006-01-27 | 2012-06-13 | ソニー株式会社 | 光記録媒体及びその製造方法 |
JP5475244B2 (ja) * | 2007-03-30 | 2014-04-16 | 株式会社Adeka | シアニン化合物、該化合物を用いた光学フィルター及び光学記録材料 |
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JP2003231359A (ja) * | 2002-02-12 | 2003-08-19 | Asahi Denka Kogyo Kk | 光学記録材料 |
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JPH11227331A (ja) | 1998-02-12 | 1999-08-24 | Hitachi Maxell Ltd | 光情報記録媒体 |
JPH11277904A (ja) | 1998-03-30 | 1999-10-12 | Hitachi Maxell Ltd | 光記録媒体 |
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JP4467206B2 (ja) | 2000-06-01 | 2010-05-26 | 株式会社Adeka | 光学記録材料 |
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 |
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2004
- 2004-11-25 JP JP2004340485A patent/JP4688480B2/ja not_active Expired - Fee Related
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2005
- 2005-10-13 KR KR1020077010936A patent/KR101272743B1/ko not_active IP Right Cessation
- 2005-10-13 WO PCT/JP2005/018852 patent/WO2006057113A1/ja active Application Filing
- 2005-10-13 CN CNA2005800386858A patent/CN101056874A/zh active Pending
- 2005-10-13 EP EP05793651.0A patent/EP1826208B1/en not_active Expired - Fee Related
- 2005-10-13 US US11/791,487 patent/US7682773B2/en not_active Expired - Fee Related
- 2005-10-13 CN CN201210063842.2A patent/CN102675304B/zh not_active Expired - Fee Related
- 2005-10-25 TW TW094137388A patent/TWI419936B/zh not_active IP Right Cessation
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JP2003231359A (ja) * | 2002-02-12 | 2003-08-19 | Asahi Denka Kogyo Kk | 光学記録材料 |
JP2004216817A (ja) * | 2003-01-17 | 2004-08-05 | Ricoh Co Ltd | 光記録媒体 |
JP2006104387A (ja) * | 2004-10-07 | 2006-04-20 | Asahi Denka Kogyo Kk | シアニン化合物及び光学記録材料 |
Also Published As
Publication number | Publication date |
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CN101056874A (zh) | 2007-10-17 |
TWI419936B (zh) | 2013-12-21 |
CN102675304B (zh) | 2014-05-07 |
KR20070085365A (ko) | 2007-08-27 |
CN102675304A (zh) | 2012-09-19 |
KR101272743B1 (ko) | 2013-06-10 |
US20080138740A1 (en) | 2008-06-12 |
EP1826208B1 (en) | 2013-05-22 |
JP2006151823A (ja) | 2006-06-15 |
TW200630437A (en) | 2006-09-01 |
WO2006057113A1 (ja) | 2006-06-01 |
EP1826208A4 (en) | 2011-10-19 |
EP1826208A1 (en) | 2007-08-29 |
US7682773B2 (en) | 2010-03-23 |
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