TWI419936B - A cyanine compound, an optical recording material using the compound, and an optical recording medium - Google Patents

A cyanine compound, an optical recording material using the compound, and an optical recording medium Download PDF

Info

Publication number
TWI419936B
TWI419936B TW094137388A TW94137388A TWI419936B TW I419936 B TWI419936 B TW I419936B TW 094137388 A TW094137388 A TW 094137388A TW 94137388 A TW94137388 A TW 94137388A TW I419936 B TWI419936 B TW I419936B
Authority
TW
Taiwan
Prior art keywords
group
optical recording
compound
cyanine compound
ring
Prior art date
Application number
TW094137388A
Other languages
English (en)
Other versions
TW200630437A (en
Inventor
Mitsuhiro Okada
Toru Yano
Koichi Shigeno
Original Assignee
Adeka Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Adeka Corp filed Critical Adeka Corp
Publication of TW200630437A publication Critical patent/TW200630437A/zh
Application granted granted Critical
Publication of TWI419936B publication Critical patent/TWI419936B/zh

Links

Classifications

    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record 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
    • G11B7/244Record 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
    • G11B7/246Record 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
    • G11B7/247Record 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
    • G11B7/2472Record 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/06Heterocyclic 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
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record 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
    • G11B7/244Record 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
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record 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
    • G11B7/244Record 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
    • G11B7/245Record 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 a polymeric component
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record 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
    • G11B7/244Record 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
    • G11B7/246Record 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
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record 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
    • G11B7/244Record 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
    • G11B7/246Record 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
    • G11B7/2467Record 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
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record 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
    • G11B7/244Record 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
    • G11B7/246Record 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
    • G11B7/248Record 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
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record 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
    • G11B7/244Record 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
    • G11B7/249Record 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
    • G11B7/2495Record 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
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record 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
    • G11B7/253Record 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
    • G11B7/2531Record 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 glass
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record 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
    • G11B7/253Record 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
    • G11B7/2533Record 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
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record 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
    • G11B7/253Record 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
    • G11B7/2533Record 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
    • G11B7/2534Record 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]
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record 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
    • G11B7/253Record 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
    • G11B7/2533Record 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
    • G11B7/2535Record 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
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record 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
    • G11B7/256Record 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
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/146Laser beam

Landscapes

  • 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

花青化合物、使用該化合物之光學記錄材料及光學記錄媒體
本發明係關於一種新穎之花青化合物、一種含有該花青化合物而成之光學記錄材料以及一種使用該光學記錄材料之光學記錄媒體。該花青化合物,作為光學要素有用,除尤其適合用於藉由雷射光進行記錄及再生之光學記錄媒體之記錄層的光學記錄材料之外,亦可作為光吸收劑而用於影像顯示裝置之光學濾光器。
於500~700nm之範圍內具有強度較大吸收之化合物,尤其是於極大吸收(λmax)為550~620nm之化合物,可使用為DVD-R等之光學記錄媒體之光學記錄層、液晶顯示裝置(LCD)、電漿顯示面板(PDP)、電致發光顯示(ELD)、陰極管顯示裝置(CRT)、螢光顯示管、電場放射型顯示器等影像顯示裝置之光學濾光器之光學要素。
作為上述之光學要素,大量研究有含有感度較高的吲哚環之花青化合物。該花青化合物,尤其為作為以DVD-R為代表的光學記錄媒體之記錄要素,由於其存有可對應於記錄之高速化之優點,故而報告例較多,例如於下述專利文獻1~5中所報導。又,於專利文獻6中,揭示有於吲哚骨架3位導入苄基之花青化合物。
但是,先前之花青系化合物,於熱分解特性上存有問題。作為可高速記錄之光學記錄媒體之記錄要素,分解溫度較低者比較適合,但是報導之上述花青系化合物,並非於此方面具有充分特性者。
專利文獻1:特開平10-278426號公報專利文獻2:特開平11-227331號公報專利文獻3:特開平11-277904號公報專利文獻4:特表2001-506933號公報專利文獻5:特開2002-52829號公報專利文獻6:特開2003-231359號公報
因此,本發明之目的在於提供一種表現出更適合於光學記錄用途之熱行為的新穎花青化合物、一種含有該者之光學記錄材料以及一種使用該光學記錄材料之光學記錄媒體。
本發明者們認為,適當化熱分解行為以及適當化吸收波長,於實現可與高速記錄相對應之感度較為有效,反覆研究之結果,發現含有特定之分子結構之花青系化合物可解決上述課題。
本發明係基於上述見解而成者,其可提供如下述通式(I)所示之化合物。
又,本發明係提供一種用於於基體上形成有光學記錄層之光學記錄媒體之該光學記錄層,且含有上述花青化合物而成之光學記錄材料。
又,本發明係提供一種於基體上形成有含有上述光學記錄材料之薄膜之光學記錄媒體。
(式中,環A以及環B表示亦可具有取代基之苯環或者萘環,R1以及R2分別獨立地表示碳原子數1~4之烷基或者亦可具有取代基之苄基,R1以及R2之至少一個為亦可具有取代基之苄基;X表示O、S或者NY,Y、Y1 以及Y2 分別獨立地表示氫原子或者碳原子數1~30之有機基,Z表示氫原子、鹵素原子或者氰基,Anm 表示m價之陰離子,m表示1或者2之整數,p表示將電荷保持為中性之係數)。
上述通式(I)所表示之本發明之花青化合物,其特徵在於其係於特定之部位,含有亦可具有取代基之苄基的新穎化合物,較用於DVD-R用途之光學記錄材料的其他花青系化合物,分解溫度較低、吸收波長適當。
上述通式(I)中,至於以環A以及環B表示之亦可具有取代基之苯環或者萘環之取代基,可列舉氟、氯、溴、碘等鹵素基;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、庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、2-乙基己基等烷基;苯基、萘基、2-甲苯基、3-甲苯基、4-甲苯基、4-乙烯苯基、3-異丙基苯基等芳基;甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、第二丁氧基、第三丁氧基等烷氧基;甲硫基、乙硫基、丙硫基、異丙硫基、丁硫基、第二丁硫基、第三丁硫基等烷硫基;硝基、氰基等。
於上述通式(I)中,以R1或者R2所表示之碳原子數1~4之烷基,可列舉甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基等。
以R1或者R2所表示之基團中,至少一個為亦可具有取代基之苄基。該苄基亦可含有之取代基數目為1或者2。作為該取代基可列舉氟、氯、溴、碘等鹵素基;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、庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、2-乙基己基等烷基;該等烷基之鹵素取代體;甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、第二丁氧基、第三丁氧基等烷氧基;該等烷氧基之鹵素取代體;甲硫基、乙硫基、丙硫基、異丙硫基、丁硫基、第二丁硫基、第三丁硫基等烷硫基;硝基;氰基;羥基等,若該取代基為較大時,花青化合物之莫耳吸光係數變小,且有時影響及感度,故而,作為具有取代基之苄基,較好的是,下述通式(II)所表示者。
(式中,m表示1~2之整數,X1 表示羥基、鹵素基、氰基、硝基、碳原子數1~4之烷基、碳原子數1~4之鹵代烷基,碳原子數1~4之烷氧基、或者碳原子數1~4之鹵代烷氧基,m為2之情形時,兩個X1 相同亦可,不同亦可)。
於上述通式(II)中,作為以X1 所表示之鹵素基,可列舉氟、氯、溴、碘等,作為碳原子數1~4之烷基,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,作為碳原子數1~4之鹵代烷基,可列舉氯代甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、氟甲基、二氟甲基、三氟甲基、全氟乙基、全氟丙基、全氟丁基等,作為碳原子數1~4之烷氧基,可列舉甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、第二丁氧基、第三丁氧基等,作為碳原子數1~4之鹵代烷氧基,氯代甲氧基、二氯甲氧基、三氯甲氧基、溴甲氧基、二溴甲氧基、三溴甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、全氟乙氧基、全氟丙氧基、全氟丁氧基等。
至於於上述通式(I)中之以Y1 或者Y2 所表示之碳原子為數1~30之有機基,無特別之限制,例如可列舉甲基、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、十六烷基、十七烷基、十八烷基等烷基;乙烯、1-甲基乙烯基、2-甲基乙烯基、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、1-苯基丙烯基-3-基等鏈烯基;苯基、萘基、2-甲苯基、3-甲苯基、4-甲苯基、4-乙烯苯基、3-異丙基苯基、4-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、4-十八烷基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4-二第三丁基苯基、環己基苯基等烷芳基;苄基、苯乙基、2-苯基丙烷-2-基、二苯基甲基、三苯基甲基、苯乙烯基、肉桂基等芳烷基;該等烴基為以醚鍵以及/或者硫醚鍵中斷而成者,例如,可列舉2-甲氧基乙基、3-甲氧基丙基、4-甲氧基丁基、2-丁氧基乙基、甲氧基乙氧基乙基、甲氧基乙氧基乙氧基乙基、3-甲氧基丁基、2-苯氧乙基、2-甲硫基乙基、2-苯硫基乙基,進而該等基團亦可被烷氧基、鏈烯基、硝基、氰基、鹵素原子等取代。
上述之Y1 以及Y2 ,若作為取代基之該等基較大,則花青化合物之莫耳吸光係數變小,存有影響及感度之情形,故而較好的是碳原子數為1~8之烴基,更好的是碳原子數為1~8之烷基。
再者,X為NY之情形時,以Y所表示之碳原子數1~30之有機基,上述之Y1 及與Y2 同樣。
至於於上述通式(I)中,以Z所表示之鹵素原子,可列舉氟、氯、溴、碘。
至於又,於上述通式(I)中,以Anm 所表示之陰離子,例如,作為一價者,可列舉,氯陰離子、溴陰離子、碘陰離子、氟陰離子等鹵素陰離子;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、四氟化硼陰離子等無機系陰離子;苯磺酸陰離子、甲苯磺酸陰離子、三氟甲基磺酸陰離子、二苯基胺基-4-磺酸陰離子、2-胺基-4-甲基-5-氯代苯磺酸陰離子、2-胺基-5-硝基苯磺酸陰離子等有機磺酸陰離子;辛基膦酸陰離子、十二烷基膦酸陰離子、十八烷基基膦酸陰離子、苯基膦酸陰離子、壬基苯基膦酸陰離子、2,2'-亞甲基雙(4,6-二第三丁基苯基)膦酸陰離子等有機膦酸系陰離子等,至於二價者,例如,可列舉苯二磺酸陰離子、萘二磺酸陰離子等。又,亦可根據需要使用含有使激發狀態之活性分子脫激發(實行驟冷)機能之驟冷劑陰離子或者於環戊二烯基環具有羧基、膦酸基、磺酸基等陰離子性基之二茂鐵、二茂非鐵金屬等茂金屬化合物陰離子等。
作為上述之驟冷陰離子,例如,可列舉於下述通式(A)或者(B)所表示者,特開昭60-234892號公報、特開平5-43814號公報、特開平6-239028號公報、特開平9-309886號公報、特開平10-45767號公報等所揭示之陰離子。
(式中,M表示鎳原子或者銅原子,R5以及R6表示鹵素原子、碳原子數1~8之烷基、碳原子數6~30之芳基或者-SO2 -Z基,Z表示亦可被烷基、鹵素原子取代之芳基、二烷胺基、二芳胺基、哌啶基或者嗎啉代基,a以及b分別表示0~4。又,R7、R8、R9以及R10分別獨立地表示烷基、烷苯基、烷氧苯基或者鹵化苯基)。
至於於上述通式(I)所表示之本發明之花青化合物之具體例,可列舉下述化合物No.1~27。再者,以下之例示中,表示省略陰離子之花青陽離子。
於上述之花青化合物中,因作為光學記錄材料之熱行為更好,故而較好的是構成鍵合亦可具有取代基之苄基之吲哚骨架的環(上述通式(I)中之環A)為萘環者(例如,化合物No.1~12、19~22、24~27),尤其是於吲哚環之e面縮合苯環者(例如,化合物No.1~4、7~12、19~22、25~27);於上述通式(I)中之環B為苯環者(例如,化合物No.1~18、20、21、23~27),更好的是上述環A為萘環並且上述環B為苯環者(例如,化合物No.1~12、20、21、24~27)。一般認為其原因為,由於亦可具有取代基之苄基與苯幷吲哚環之立體障害所造成之環結構之偏度變得更大。
於上述通式(I)所表示之本發明之花青化合物,並非根據其製造法受到限制者。該花青化合物,例如可使作為中間體之2-甲基噻唑鹽衍生物以及2-甲基吲哚4級鹽衍生物,與N,N'-二苯基甲脒等橋接劑反應而獲得。又,亦可具有取代基之苄基,可於獲得作為中間體之2-甲基吲哚4級鹽衍生物之過程中導入,將芳肼衍生物作為起始原料,藉由於4位含有亦可具有取代基X1之苯基之2-丁酮衍生物形成吲哚環時導入亦可,於吲哚環使鹵化甲基苯衍生物反應而導入亦可。Y1或者Y2,可藉由與芳胺衍生物或者吲哚環之NH反應之Y1-D或者Y2-D(D為氯、溴、碘等鹵素基;苯基醯氧基、4-甲苯基醯氧基、4-氯代苯基醯氧基等醯氧基)導入。再者,於4位含有亦可具有取代基X1之苯基之2-丁酮衍生物,可藉由丙酮與亦可具有取代基X1之苯甲醛反應而容易地獲得。作為獲得本發明之花青化合物之具體的方法之一例,可列舉於下述[化7]所表示之反應路線。
(式中,環A、環B、R2、Y1 、Y2 、X、X1 以及m與上述通式(I)以及(H)相同。An1 、An2 以及An 表示陰離子)。
本發明之花青化合物係作為光學要素起作用者,特別適合使用於光學記錄媒體之光學記錄層。含有本發明之花青化合物之光學記錄層,使用含有本發明之花青化合物之光學記錄材料,於基體上形成為薄膜。再者,本發明之光學記錄材料包含本發明之花青化合物本身,以及本發明之花青化合物與下述有機溶劑以及/或者各種化合物之混合物。
關於使用有本發明之光學記錄材料之光學記錄媒體之光學記錄層之形成方法,並非特別限制。一般而言,可使用如下之之濕式塗布法:於甲醇、乙醇等低級醇類;甲基溶纖劑、乙基溶纖劑、丁基溶纖劑、丁基二醇等醚醇類;丙酮、丁酮、甲基異丁基酮、環己酮、二丙酮醇等酮類;乙酸乙酯、乙酸丁酯、乙酸甲氧基乙酯等酯類;丙烯酸乙酯、丙烯酸丁酯等丙烯酸酯類;2,2,3,3-四氟丙醇等氟化醇類;苯、甲苯、二甲苯等烴類;二氯甲烷、二氯乙烷、氯仿等氯化烴類等有機溶劑中,溶解有本發明之花青化合物以及根據需要溶解有下述之各種化合物之溶液,將該溶液以旋塗、噴射、浸漬等方式塗布於基體上。至於其他的方法,可列舉蒸鍍法、濺鍍法等。
使用本發明之光學記錄材料而形成之上述光學記錄層之厚度,通常為0.001~10 μm,較好的是於0.01~5 μm之範圍較適當。
又,於光學記錄媒體之光學記錄層含有本發明之光學記錄材料時,於該光學記錄層中本發明之花青化合物之含量,較好的是50~100質量%。為形成如此之花青化合物含量之光學記錄層,較好的是本發明之光學記錄材料,以於本發明之光學記錄材料中所含有之固形分為基準%含有50~100質量%本發明之花青化合物。
又,上述光學記錄層,除本發明之花青化合物之外,根據需要,亦可含有於其他花青系化合物、偶氮系化合物、酞花青系化合物、卟吩系化合物等使用於光學記錄層之化合物;聚乙烯、聚酯、聚苯乙烯、聚碳酸酯等樹脂類;界面活性劑;靜電防止劑;滑劑;難燃劑;受阻胺等自由基捕捉劑;二茂鐵衍生物等凹陷形成促進劑;分散劑;抗氧化劑;交聯劑;耐光性賦予劑等。進而、上述光學記錄層,作為單線態氧等驟冷劑,亦可含有芳香族亞硝基化合物、銨化合物、亞胺正離子化合物、雙亞胺正離子化合物、過渡金屬螯合化合物等。
該等各種化合物,於上述光學記錄層中,較好的是於0~50質量%之範圍內使用。因此,較好的是於本發明之光學記錄材料中,該等各種化合物含量,以於本發明之光學記錄材料中所含有之固形分為基準為0~50質量%。
設有上述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,並無特別之限制。例如,可使用聚甲基丙烯酸甲酯、聚對苯二甲酸乙二酯、聚碳酸酯等樹脂、玻璃等。又,其形狀根據用途可為膠帶、鼓、皮帶、園盤等任意形狀。
又,於上述光學記錄層上,亦可使用金、銀、鋁、銅等,藉由蒸鍍法或者濺鍍法形成反射膜,亦可形成丙烯樹脂、紫外線硬化性樹脂等之保護層。
本發明之光學記錄材料,適用於將半導體雷射用於記錄以及再生的光學記錄媒體,尤其適用於高速記錄型之DVD-R等光碟。
實施例
以下,以實施例及評價例進而對本發明加以詳細之說明。但本發明並非受以下實施例任何限制者。
[實施例1]化合物No.2之六氟化磷鹽製造
於反應燒瓶中,裝入2.9 g(0.005 mol)之下述[化8]所表示之吲哚衍生物A、2.0 g(0.005 mol)之自下述[化9]所表示之合成反應路線所獲得之中間體B以及4.2 g(0.05 mol)之吡啶,升溫至40℃,攪拌均勻。滴下0.8 g(0.0075 mol)之無水乙酸,使之反應4小時。冷卻後,以40 g氯仿/30 g水洗淨2次,繼而,以3 g(0.015 mol)之六氟化磷鈣水溶液進行2次鹽交換後,水洗2次。以蒸發器脫溶劑後,以35 g之甲醇進行晶析。藉由過濾、甲醇洗淨、真空乾燥,獲得2.6 g之灰色固體(收率74%)。分析之結果,可確認所獲得之灰色固體係目的物(化合物No.2之六氟化磷鹽)。分析結果如下所示。
分析結果.光學特性(氯仿,1.01×10 6 莫耳/升)λmax;584 nm、ε;1.2×105 .吸熱溫度(於氮氣中以10℃/分之升溫條件下的TG/DTA測定之吸熱峰值)213.1℃.分子量(TOF-MS光譜分析)660.7.1 H-NMR(溶劑;DMSO)
圖1表示1 H-NMR光譜。
[實施例2]化合物No.8之六氟化磷鹽之製造
於反應燒瓶中,裝入16.5 g之上述吲哚衍生物A、8.7 g(0.03 mol)之下述[化10]所表示之中間體C,以及47.4 g(0.6 mol)之吡啶,進行攪拌。於室溫滴下4.6 g(0.045 mol)之無水乙酸,使之反應15小時。以150 g氯仿/100 g水進行2次洗淨後,於5.5 g(0.03 mol)之六氟化磷鈣水溶液中進行鹽交換1次,繼而水洗2次。藉由蒸發器使之脫溶劑而獲得原料。將所獲得原料進行管柱提純(乙酸乙酯:己烷=1.5:1,原點甲醇萃取),藉由濃縮獲得1.8 g之紫色固體。進而,藉由二甲基乙醯胺/甲醇實行再晶析,獲得紫色固體1.3 g(收率7%)。分析之結果,確認所獲得之紫色固體為目的物(化合物No.8之六氟化磷鹽)。分析結果如下所示。
分析結果.光學特性(氯仿,9.81×10 6 莫耳/升)λmax;547 nm、ε;1.14×105。.吸熱溫度(於氮氣中以10℃/分之升溫條件下的TG/DTA測定之吸熱峰值)218.4℃.分子量(TOF-MS光譜分析)616.6.1 H-NMR(溶劑;DMSO)
圖2表示1 H-NMR光譜。
[評價例1]
關於於上述實施例中所獲得之化合物No.2及8以及以下[化11]所表示之比較化合物1,進行於氮氣流中之示差熱分析,測定熱分解溫度。熱分解溫度為於氮氣中以10℃/分之升溫條件下的DTA之發熱峰值之溫度。結果表示於表1。
根據上述表1之結果,可確認本發明之花青化合物熱分解溫度較低。該現象表示本發明之花青化合物作為光學記錄材料適合於高速記錄。
[實施例3]
將合物No.2之六氟化磷鹽以成為濃度1質量%之方式溶解於2,2,3,3-四氟丙醇中,獲得光學記錄材料。塗布鈦螯合化合物(T-50:日本曹達公司製造)後,進行加水分解,將上述光學記錄材料以旋塗塗敷法塗布(以回轉數2000 rpm下回轉塗布1分鐘)於設置有基礎層(0.01 μm)的直徑12 cm之聚碳酸酯碟形基板上,獲得光學記錄媒體。關於該光學記錄媒體,進行透過光紫外線光譜之測定,λmax為598 nm,可確認上述光學記錄材料為作為DVD-R用之光學記錄材料適合者。
[實施例4]
除使用化合物No.8之六氟化磷鹽代替化合物No.2之六氟化磷鹽以外,與實施例3相同地製作光學記錄材料,使用該光學記錄材料獲得光學記錄媒體。關於該光學記錄媒體,進行透過光紫外線光譜之測定,λmax為558 nm,可確認上述光學記錄材料作為DVD-R用之光學記錄材料適合者。
產業上之可利用性
藉由本發明,可提供一種表現更適合於光學記錄用途之熱行為的新穎花青化合物、一種含有該者之光學記錄材料以及一種使用該光學記錄材料之光學記錄媒體。
圖1-a係表示於實施例1中所獲得之化合物No.2之六氟化磷鹽之1 H-NMR光譜。
圖1-b係表示圖1-a之部分擴大圖。
圖1-c係表示圖1-a之部分擴大圖。
圖2-a係表示於實施例2中所獲得之化合物No.8之六氟化磷鹽之1 H-NMR光譜。
圖2-b係圖2-a之部分擴大圖。
圖2-c係圖2-a之部分擴大圖。

Claims (9)

  1. 一種花青化合物,其係以下述通式(I)所表示之花青化合物, (式中,環A以及環B表示亦可具有取代基之苯環或者萘環,R1以及R2分別獨立地表示碳原子數1~4之烷基或者亦可具有取代基之苄基,R1以及R2之至少一個為亦可具有取代基之苄基;X表示O、S或者NY,Y、Y1 以及Y2 分別獨立地表示氫原子或者碳原子數1~30之有機基,Z表示氫原子、鹵素原子或者氰基,Anm- 表示m價之陰離子,m表示1或者2之整數,p表示將電荷保持為中性之係數)。
  2. 如請求項1之花青化合物,其中於上述通式(I)中之環B為苯環。
  3. 如請求項1之花青化合物,其中於上述通式(I)中之X為S。
  4. 如請求項1之花青化合物,其中於上述通式(I)中之X為O。
  5. 如請求項1之花青化合物,其中於上述通式(I)中環A為萘環。
  6. 如請求項1之花青化合物,其中於上述通式(I)中Y1 以及Y2 為碳原子數1~8之烷基。
  7. 如請求項1之花青化合物,其中於上述通式(I)中R1以及R2 之任何一個為甲基。
  8. 一種光學記錄材料,其特徵為:其使用於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,且含有請求項1至7中任一項之花青化合物而形成。
  9. 一種光學記錄媒體,其特徵為:於基體上形成有含有請求項8之光學記錄材料之薄膜。
TW094137388A 2004-11-25 2005-10-25 A cyanine compound, an optical recording material using the compound, and an optical recording medium TWI419936B (zh)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number Publication Date
TW200630437A TW200630437A (en) 2006-09-01
TWI419936B true TWI419936B (zh) 2013-12-21

Family

ID=36497857

Family Applications (1)

Application Number Title Priority Date Filing Date
TW094137388A TWI419936B (zh) 2004-11-25 2005-10-25 A cyanine compound, an optical recording material using the compound, and an optical recording medium

Country Status (7)

Country Link
US (1) US7682773B2 (zh)
EP (1) EP1826208B1 (zh)
JP (1) JP4688480B2 (zh)
KR (1) KR101272743B1 (zh)
CN (2) CN101056874A (zh)
TW (1) TWI419936B (zh)
WO (1) WO2006057113A1 (zh)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1438639A (zh) * 2002-02-12 2003-08-27 旭电化工业株式会社 光学记录材料
JP2004195765A (ja) * 2002-12-18 2004-07-15 Taiyo Yuden Co Ltd 光情報記録媒体

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS526617B1 (zh) * 1970-12-29 1977-02-23
DE69725607T2 (de) 1996-12-20 2004-08-05 Ciba Speciality Chemicals Holding Inc. Polymethin-komplex-farbstoffe und ihre verwendung
JPH10278426A (ja) 1997-04-04 1998-10-20 Hitachi Maxell Ltd 光記録媒体
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
US6306478B1 (en) * 2000-01-06 2001-10-23 Ritek Corporation Asymmetrical trimethine cyanine dyes for high capacity optical recording medium
JP2001192579A (ja) * 2000-01-11 2001-07-17 ▲らい▲とく▼科技股▲ふん▼有限公司 高容量光記録媒体用の非対称トリメチン・シアニン染料
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
JP3847637B2 (ja) 2002-02-21 2006-11-22 株式会社リコー 光記録媒体
JP2004098542A (ja) * 2002-09-11 2004-04-02 Tdk Corp 光記録媒体及び光記録再生方法
JP4105555B2 (ja) * 2003-01-17 2008-06-25 株式会社リコー 光記録媒体
JP4488762B2 (ja) * 2003-04-04 2010-06-23 株式会社Adeka シアニン化合物、光学フィルター及び光学記録材料
JP3708094B2 (ja) * 2003-08-07 2005-10-19 旭電化工業株式会社 シアニン化合物、光学記録材料及び光学記録媒体
JP3698708B2 (ja) * 2003-08-07 2005-09-21 旭電化工業株式会社 シアニン化合物、光学記録材料及び光学記録媒体
JP4255359B2 (ja) * 2003-10-31 2009-04-15 ソニー株式会社 光記録媒体及び光記録再生方法
CN100581837C (zh) * 2004-07-29 2010-01-20 株式会社艾迪科 光学记录材料和光学记录介质
JP4640769B2 (ja) * 2004-10-07 2011-03-02 株式会社Adeka シアニン化合物及び光学記録材料
JP4986457B2 (ja) * 2005-04-05 2012-07-25 株式会社Adeka シアニン化合物、光学フィルター及び光学記録材料
JP5004506B2 (ja) * 2005-06-24 2012-08-22 株式会社Adeka 光学フィルター
CN101410460B (zh) * 2006-03-31 2013-01-09 株式会社艾迪科 花青化合物以及光学记录材料

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1438639A (zh) * 2002-02-12 2003-08-27 旭电化工业株式会社 光学记录材料
JP2004195765A (ja) * 2002-12-18 2004-07-15 Taiyo Yuden Co Ltd 光情報記録媒体

Also Published As

Publication number Publication date
CN102675304B (zh) 2014-05-07
JP4688480B2 (ja) 2011-05-25
CN101056874A (zh) 2007-10-17
CN102675304A (zh) 2012-09-19
JP2006151823A (ja) 2006-06-15
EP1826208B1 (en) 2013-05-22
US7682773B2 (en) 2010-03-23
WO2006057113A1 (ja) 2006-06-01
TW200630437A (en) 2006-09-01
KR20070085365A (ko) 2007-08-27
EP1826208A1 (en) 2007-08-29
US20080138740A1 (en) 2008-06-12
KR101272743B1 (ko) 2013-06-10
EP1826208A4 (en) 2011-10-19

Similar Documents

Publication Publication Date Title
JP3698708B2 (ja) シアニン化合物、光学記録材料及び光学記録媒体
TWI385151B (zh) Cyanine compounds (CYANINE) compounds and optical recording materials
JP4679520B2 (ja) 光学記録材料及び光学記録媒体
KR100814215B1 (ko) 광학기록 재료
TWI397561B (zh) Anthocyanin compounds and optical recording materials
JP3708094B2 (ja) シアニン化合物、光学記録材料及び光学記録媒体
TWI419936B (zh) A cyanine compound, an optical recording material using the compound, and an optical recording medium
JP2004002847A (ja) フォトクロミック蛍光重合体およびその製造方法
TWI411605B (zh) A cross-linked anthocyanin compound and an optical recording material using the compound
JP4488963B2 (ja) 光学記録材料
JP4467206B2 (ja) 光学記録材料
TWI436979B (zh) Indolium (INDOLIUM) compound and an optical recording material using the same
TWI412033B (zh) Optical recording materials and anthocyanin compounds
JP4076308B2 (ja) 光学記録材料
JP4265724B2 (ja) 光学記録材料
TWI407434B (zh) An optical recording material and an optical recording medium including the same
JP5426158B2 (ja) メチン系色素とその用途
TWI383896B (zh) Optical recording materials, chalcone compounds and metal complexes
JP2002264504A (ja) 光学記録材料
JP2007055043A (ja) 光学記録材料及び光学記録媒体

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees