JPH01141795A - Optical information recording medium - Google Patents
Optical information recording mediumInfo
- Publication number
- JPH01141795A JPH01141795A JP62300249A JP30024987A JPH01141795A JP H01141795 A JPH01141795 A JP H01141795A JP 62300249 A JP62300249 A JP 62300249A JP 30024987 A JP30024987 A JP 30024987A JP H01141795 A JPH01141795 A JP H01141795A
- Authority
- JP
- Japan
- Prior art keywords
- group
- recording medium
- optical information
- phthalocyanine
- information recording
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 229910052718 tin Inorganic materials 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims description 16
- 239000000975 dye Substances 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 10
- 239000010408 film Substances 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000001007 phthalocyanine dye Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 abstract description 17
- 230000006866 deterioration Effects 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 10
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 238000007740 vapor deposition Methods 0.000 abstract description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 14
- 238000002834 transmittance Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 9
- -1 phthalocyanine compound Chemical class 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CMWRUTZCSFMXJQ-UHFFFAOYSA-N bis(triphenylsilyloxy)silicon Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si]O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CMWRUTZCSFMXJQ-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- JACPFCQFVIAGDN-UHFFFAOYSA-M sipc iv Chemical compound [OH-].[Si+4].CN(C)CCC[Si](C)(C)[O-].C=1C=CC=C(C(N=C2[N-]C(C3=CC=CC=C32)=N2)=N3)C=1C3=CC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 JACPFCQFVIAGDN-UHFFFAOYSA-M 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910004657 CaNi5 Inorganic materials 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920000620 organic polymer Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- UZRUZACOSHWLOC-UHFFFAOYSA-M phenoxyaluminum Chemical compound [Al]OC1=CC=CC=C1 UZRUZACOSHWLOC-UHFFFAOYSA-M 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
- G11B7/248—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
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、光学的情報記録媒体、特に、色素を含む有機
薄膜を備えた光学的情報記録媒体に関する。更に詳しく
は１、し・−ザビームにより直接記録し、反射率の変化
による情報の再生に用いられる光学的情報記録媒体に関
する９
〔従来の技術〕
光学的情報記録媒体は、媒体と記録ないし再生ヘッドが
非接触であるので、記録媒体が摩耗劣化しないという特
徴をもち、種々の記録媒体の開発研究ガ行われている。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an optical information recording medium, and particularly to an optical information recording medium provided with an organic thin film containing a dye. For more details, refer to 1. - Optical information recording medium used for direct recording with the beam and reproduction of information by changing reflectance 9 [Prior art] An optical information recording medium consists of a medium and a recording or reproducing head. Since the recording medium is non-contact, it has the characteristic that the recording medium does not deteriorate due to wear and tear, and research and development of various recording media are being carried out.
特に、ヒ・−トモ−ド記餘方式の分野では、低融点金属
、有機高分子化合物、あるいは、色素が融解、蒸発、あ
るいは、昇華する物質として提案されており、中でも有
機高分子化合物や色素を含む有機薄膜は、熱伝導率が小
さく、また、融解、ないし、昇乍渇度が舒いため、記録
感度の点で好ましく、シアニン色素、スクワリリウム色
素など種々の物質が提案されている。In particular, in the field of heat mode recording, low melting point metals, organic polymer compounds, or dyes have been proposed as substances that melt, evaporate, or sublimate. An organic thin film containing the above is preferable in terms of recording sensitivity because it has a low thermal conductivity and a low melting or increasing degree of depletion, and various substances such as cyanine dyes and squarylium dyes have been proposed.
従来、色素の記録層として適用した光学的情報記録媒体
は、特開昭５６−１６９４８号公報などで公知である。Conventionally, an optical information recording medium applied as a dye recording layer is known from, for example, Japanese Patent Laid-Open No. 16948/1983.
しかし、この種の色素薄膜Ｖ、録層を反射型の光学的情
報記録媒体として利用するには金属扉Ｍ膜を必要とし、
そのため、媒体購成が複雑にな“つたり、情報の記録再
生特性が劣るなどの問題がある。これに対し、色素自体
の反射率が適度に高いシアニン系色素等を用いることが
、特開昭６０−７８７８７号公報等により提案されてい
る。しかし、シアニン系色素は一般に耐光性が低いため
、書き込み後の読み出しの際、読み出し光の繰返し照射
によって色素が脱色し、読み出しのＳ／Ｎ比が低下して
しまう、いわゆる、再生劣化が大きいという問題がある
。一方、耐光堅ろう性の優れた色素どしてフタロシアニ
ン化合物を記録層に用いることが特開昭５８−５６８９
２号公報等により提案されている。However, in order to use this type of dye thin film V and recording layer as a reflective optical information recording medium, a metal door M film is required.
As a result, there are problems such as complicated media purchasing and poor information recording and reproducing characteristics. This has been proposed in Japanese Patent No. 60-78787, etc. However, since cyanine dyes generally have low light resistance, when reading after writing, the dye is bleached by repeated irradiation with read light, resulting in a decrease in the read S/N ratio. There is a problem of large playback deterioration, which is a decrease in the light resistance.On the other hand, the use of a phthalocyanine compound as a dye with excellent light fastness in the recording layer was disclosed in Japanese Patent Application Laid-Open No. 58-5689.
This is proposed in Publication No. 2, etc.
しかし、フタロシアニン化合物の反射率は、−般に、シ
アニン系色素に比べて低く、記録再生特性の点で十分満
足できるものではない。However, the reflectance of phthalocyanine compounds is generally lower than that of cyanine dyes, and is not fully satisfactory in terms of recording and reproducing characteristics.
本発明の目的は、優れた記録再生特性をもち、改善され
た再生劣化特性の光学的情報記録媒体を提供することに
ある。An object of the present invention is to provide an optical information recording medium having excellent recording and reproducing characteristics and improved reproduction deterioration characteristics.
本発明は、基板上に下記一般式［Ｉ］で表わされるフタ
ロシアニン系色素を主成分とする有機薄膜が形成されて
いることを特徴とする。The present invention is characterized in that an organic thin film containing a phthalocyanine dye represented by the following general formula [I] as a main component is formed on a substrate.
・・・ＣＩ］
Ｅ式中、Ｒ１−Ｒ４は、同一、又は、異なり、直鎖、ま
たは、分岐アルキル基、アルコキシ基、ハロゲンよりな
る群より選ばれ、ｎは同一、又は。...CI] E In the formula, R1-R4 are the same or different, and are selected from the group consisting of a linear or branched alkyl group, an alkoxy group, and a halogen, and n is the same or.
異なり、０〜４の整数、Ｙｌ及びＹ２は同一、又は、異
なり、 Ｒｖ Ａ ｒ ｓ ＯＲｒ ＯＡ ｒ ？ ０
５ｉ（Ｒ）ｓ ｔＯ８ｉ Ａ ｒａよりなる群から選択
した基（ただし、ＲはＣＩ ＝ Ｃｉｓの直鎖、または
、分岐アルキル基、Ａｒはフェニル基、置換フェニル基
よりなる群から選択した基である）を示し、ＭはＡＱ、
Ｓｉ。different, integers from 0 to 4, Yl and Y2 are the same or different, Rv A r s ORr OA r ? 0
A group selected from the group consisting of 5i(R)s tO8i A ra (where R is a straight chain of CI = Cis or a branched alkyl group, and Ar is a group selected from the group consisting of a phenyl group or a substituted phenyl group) ), M is AQ,
Si.
Ｇｅ、Ｓｎよりなる群より選択された元素を示す。Indicates an element selected from the group consisting of Ge and Sn.
ただし５ＭがＡＭの時は、ＹｌのみがＭに結合している
ものとする。］
本発明者らは、ある種のフタロシアニン化合物か、シア
ニン色素と同等、又は、その以上の反射率をもち、かつ
、再生劣化特性が優れていることを見い出した。However, when 5M is AM, it is assumed that only Yl is bonded to M. ] The present inventors have discovered that a certain phthalocyanine compound has a reflectance equal to or higher than that of a cyanine dye, and has excellent reproduction deterioration characteristics.
本発明の光学的情報記録媒体は、基板上に本発明の上記
フタロシアニン系色素を主成分とする記録層を設けたも
のであるが、必要に応じて下地層や保護層などの他の層
を設けることができる。The optical information recording medium of the present invention has a recording layer containing the above-mentioned phthalocyanine dye of the present invention as a main component on a substrate, but other layers such as a base layer and a protective layer may be provided as necessary. can be provided.
本発明で使用きれる基板＋４料は、当卒者には既知の４
・ノのであり、使用１ノ〜ザ・〜光に対して透明。The substrate + 4 materials that can be used in the present invention are 4 materials known to those skilled in the art.
・It is transparent to light when used.
又は、不透明のいずれでも良い。しかし５基扼側から、
ｌノー・−ザ・−光で書き込み、読み出しを行う場合は
、レー・−・ザ・−光に対し４て透明でな１．５ればな
らない９一方、２基板と反対側、すなわち、記＠層側か
ら書き込み、読み出しを行う場合は、ｉノーザー光に対
して透明である必要はない、基板の材質は、ガラス、石
英、セラミック、プラスチック、紙、板状、又は、箔状
の金属など、一般に使用されている記録材料の支持体で
良い、また、基板には、必要に応じて凹凸で形成される
案内溝を設けても良い。Alternatively, it may be opaque. However, from the 5 group side,
When writing and reading with no-the-light, it must be 1.5 transparent to the laser light.9 On the other hand, 2. @When writing and reading from the layer side, it is not necessary to be transparent to the i-norther light.The material of the substrate may be glass, quartz, ceramic, plastic, paper, plate-shaped, or foil-shaped metal. The substrate may be a support for a commonly used recording material, and the substrate may be provided with guide grooves formed by projections and depressions as necessary.
本発明の一般式［Ｉ］で示されるフタロシアニン系色素
の主成分とする有機薄膜は非常に高い反射率を示すため
、金属反射膜を特別に設けなくても、光学的情報記録媒
体として用いることができる。すなわち、反射膜を特別
に設けないので、それだけ、製造工程が簡単になり、か
つ、低フストで製造できるばかりでなく、記録再生特性
も、反射Ｉｌ！２を・設げブー場合＋、＋Ｘ比べて、感
度並びに再生ＣＮ比が良くなる。Since the organic thin film containing the phthalocyanine dye represented by the general formula [I] of the present invention as a main component exhibits extremely high reflectance, it can be used as an optical information recording medium without a special metal reflective film. Can be done. In other words, since no special reflective film is provided, the manufacturing process is simplified and can be manufactured with low production cost, as well as the recording and reproducing characteristics are improved to reflect the reflective Il! If 2 is set, the sensitivity and reproduction CN ratio will be better than + and +X.
本発明の一般式ｒＨ］で、Ｒ，ｔ＝Ｒａの例は、メチル
基、エチル基６ブロビル基、イソプロピル基１．ｎ・−
ブチル基、１−−ブチル基、ｎ−ペンチル法。Ｓ〜ルア
ミル、１−−アミル基、ｔ−ヘプチル基、１．−オクチ
ル基、に一ドデシル基、メトキシ基、エト・キシ基、プ
ロポキシ基、イソプロポキシ基、ブトキシ基、アミ１〕
キシ基、塩素、臭素、フッ素などがある。Ｙｌ及びＹ２
の例は、メチル基、エチル基、エトキシ基、メトキシ基
、ペントキシ基、オクトキシ基、フェノキシ井、オクタ
デシルオキシ基、トリメチルシリルオキシ基、トリエチ
ルシリルオキシ基、トリフェニルシリルオキシ基、トリ
（ｎ−ヘキシル）シリルニオキシ基、トリフェニルメ
チルオキシ基などが挙げられる、また、本発明に使用さ
れるフタロシアニン化合−物の具体例は以下のものを挙
げることができる。In the general formula rH of the present invention, examples of R, t=Ra are methyl group, ethyl group, brobyl group, isopropyl group, 1. n・-
Butyl group, 1--butyl group, n-pentyl method. S~ruamyl, 1-amyl group, t-heptyl group, 1. -Octyl group, monododecyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, amine 1]
These include the xyl group, chlorine, bromine, and fluorine. Yl and Y2
Examples include methyl, ethyl, ethoxy, methoxy, pentoxy, octoxy, phenoxy, octadecyloxy, trimethylsilyloxy, triethylsilyloxy, triphenylsilyloxy, tri(n-hexyl) Specific examples of the phthalocyanine compounds used in the present invention include silylnioxy groups, triphenylmethyloxy groups, and the like.
（１） Ｐｃ５ｉ（Ｏ３ｉ（ｒ＋−Ｃａｌ（ｔａ）ａ）
ｚビス−（トリへキシルシリルオキシ）−シリコンフタ
ロシアニン
上記式で、Ｐｃはフタロシアニン骨格を表す（以下同じ
）。(1) Pc5i(O3i(r+-Cal(ta)a)
zBis-(trihexylsilyloxy)-silicon phthalocyanine In the above formula, Pc represents a phthalocyanine skeleton (the same applies hereinafter).
（２’） Ｐｃ５ｉ（Ｏ３ｉ（ＣｚＨｓ）ａ）ｚビス−
（ト・リエチルシリルオキシ）−シリコンフタロシアニ
ン
（３） Ｐｃ５ｉ（ＯＣｅＨｓｌｚ
ビスフェノキシシリコンフタロシアニン（４） Ｐｃ５
ｉ（Ｏ５ｉ（ＣｅＨｓ）ａ）ｚビス−（トリフェニルシ
リルオキシ）−シリコンフタロシアニン
（５） ＰｅＳｎ［０Ｓｉ（ＣｚＨｓ）ａ］ｚビス−（
トリエチルシリルオキシ）−スズナフタロシアニン
（６） （ｔ−Ｂｕ）ｉＰｅｓｉ（Ｏ５ｉ（ＣｚＨａ
）ａ）ｚビス（トリエチルシリルオキシ）シリコン−テ
トラキス（ｔ−ブチル）フタロシアニン（７） （ｔ−
Ｂｕ）４ＰｃＧｅ（Ｏ５ｉ（ＣＪｓ）ｓ）ｚビス（トリ
ブチルシリルオキシ）ゲルマニウム−テトラキス（ｔ−
ブチル）フタロシアニン（８） （ｔ−Ｂｕ）４Ｐｃ
Ｓｎ（Ｏ５，１（Ｃａ旧、ａ）、ｓ）ｚビス（トリへキ
シルシリルオキシ）スズ−テトラキス（ｔ−ブチル）フ
タロシアニン
（９） Ｐ ｃ Ａ Ｑ ０ＣｓＨｓ
フエノキシアルミニウムフタロシアニン（１０）Ｃ１ａ
ＰｃＳｉ（Ｏ５ｉ（ＣａＮｉ５）ａ）ｚビス（トリオク
チルシリルオキシ）シリコン−テトラクロロフタロシア
ニン
これらのフタロシアニン化物台は、ジャーナル・オブ・
アメリカン・ケミカル・ソサエティ（Ｊ。(2') Pc5i(O3i(CzHs)a)zbis-
(triethylsilyloxy)-silicon phthalocyanine (3) Pc5i (OCeHslz bisphenoxy silicon phthalocyanine (4) Pc5
i(O5i(CeHs)a)zbis-(triphenylsilyloxy)-silicon phthalocyanine (5) PeSn[0Si(CzHs)a]zbis-(
triethylsilyloxy)-tinnaphthalocyanine (6) (t-Bu)iPesi(O5i(CzHa
) a) z-bis(triethylsilyloxy)silicon-tetrakis(t-butyl)phthalocyanine (7) (t-
Bu)4PcGe(O5i(CJs)s)zbis(tributylsilyloxy)germanium-tetrakis(t-
butyl) phthalocyanine (8) (t-Bu)4Pc
Sn(O5,1(Ca old, a), s)z bis(trihexylsilyloxy)tin-tetrakis(t-butyl)phthalocyanine (9) P c A Q 0CsHs Phenoxyaluminum phthalocyanine (10) C1a
PcSi(O5i(CaNi5)a)zbis(trioctylsilyloxy)silicon-tetrachlorophthalocyanine These phthalocyanides are listed in the Journal of
American Chemical Society (J.
＾ｍｅｒ、 Ｃｈｅｗ、 Ｓｏｃ、） １９８４年、１
０６巻、第７４０４頁から第７４１０頁あるいはインオ
ーガニック・ケミストリ （Ｉｎｏｒｇ、 Ｃｈｅｗ、
） １９６７年６巻第１８６９頁から１８７２頁等に記
載される公知の方法で製造し得る。^mer, Chew, Soc,) 1984, 1
Volume 06, pages 7404 to 7410 or Inorganic Chemistry (Inorg, Chew,
), Vol. 6, pp. 1869-1872, 1967.
本発明における記録層の形成は、塗布法、ないし、蒸着
法によって行うことができる。塗布法を用いる場合には
、トルエン、クロロホルム、ジクロロエタン、トリクロ
ロエタン、メチルエチルケトンなどの溶媒を用いてスプ
レ、ローラコーチイン、グ、スピンコーティング、ディ
ッピングなどにより行われる。The recording layer in the present invention can be formed by a coating method or a vapor deposition method. When a coating method is used, spraying, roller coating, coating, spin coating, dipping, etc. are carried out using a solvent such as toluene, chloroform, dichloroethane, trichloroethane, or methyl ethyl ketone.
本発明は、６００〜９００ｎｍの波長域に適度の吸収率
及び反射率を示し、かつ、耐光性に優れた特定のフタロ
シアニン化合物を主成分とする有機薄膜を記録層として
採用することによりなされたもので、優れた記録再生特
性と改善された再生劣化特性を兼備する。The present invention has been achieved by employing as a recording layer an organic thin film mainly composed of a specific phthalocyanine compound that exhibits appropriate absorption and reflectance in the wavelength range of 600 to 900 nm and has excellent light resistance. It has both excellent recording and reproduction characteristics and improved reproduction deterioration characteristics.
以下に、本発明の具体的実施例をあげて、本発明を更に
詳細に説明するが、これはもちろん、本発明を限定する
ものではない。The present invention will be explained in more detail below with reference to specific examples, but the present invention is of course not limited to these.
〈実施例１〉
先に例示したＰｅ５ｊ（Ｏ５ｉ（ＣｅＨｓ）ａ）ｚ 、
ビス−（トリフェニルシリルオキシ）−シリコンフタロ
シアニンを公知の方法に準じて合成し、ガラス基板上に
蒸着し、厚さ５０ｎ謙の記録層を得た。この記録層の分
光特性を第１図に示す、すなわち、第１図はビス−（ト
リフェニルシリルオキシ）−シリコンフタロシアニン蒸
着膜の反射率及び透過率（％。<Example 1> Pe5j(O5i(CeHs)a)z exemplified above,
Bis-(triphenylsilyloxy)-silicon phthalocyanine was synthesized according to a known method and deposited on a glass substrate to obtain a recording layer with a thickness of 50 nm. The spectral characteristics of this recording layer are shown in FIG. 1. That is, FIG. 1 shows the reflectance and transmittance (%) of the bis-(triphenylsilyloxy)-silicon phthalocyanine vapor-deposited film.
縦軸）と波長（ｎｍ、横軸）との関係を示すグラフであ
る。第１図において、１は透過率、２は反射率（入射角
５°）を示す、この記録媒体に波長６９０ｎ＋ｍのレー
ザー光をガラス基板上から照射し、記録特性を評価した
ところ、５ｍＷ、２００ｎｓで記録が可能であった。一
方、再生劣化に対する安定性を評価すべく、１ｍＷの読
み出し光を繰り返し照射したが、百万回繰り返しても反
射率変化が生じなかった。It is a graph showing the relationship between the vertical axis) and the wavelength (nm, horizontal axis). In Fig. 1, 1 indicates transmittance and 2 indicates reflectance (incident angle 5°). When this recording medium was irradiated with a laser beam with a wavelength of 690n+m from above the glass substrate and the recording characteristics were evaluated, it was found that 5mW, 200ns It was possible to record. On the other hand, in order to evaluate stability against reproduction deterioration, 1 mW readout light was repeatedly irradiated, but no change in reflectance occurred even after 1 million repetitions.
〈実施例２〉
公知の方法に準じて合成したＰｃ５ｉ（ＯＣｓＨ５）ｚ
ビスフェノキシシリコンフタロシアニンをガラス基板上
に蒸着し、厚さ６０ｎｍの記録層を得た。この記録層の
分光特性を第２図に示す、すなわち、第２図は、ビスフ
ェノキシシリコンナフタロシアニン蒸着膜の反射率及び
透過率（％、縦軸）と波長（ｎｍ、横軸）との関係を示
すグラフである。１は透過率、２は反射率（入射角５°
）を示す。この記録媒体に波音７８０ｎｍのレーザー光
をガラス基板側から照射し、記録特性を評価したところ
、線速０．５ ｍ７秒、７．５ ｍＷで記録が可能であ
った。一方、再生劣化に対する安定性を評価するべく、
１ｍＷの読み出し光を繰り返し照射したが、百万回繰り
返しても反射率変化が生じなかった。<Example 2> Pc5i(OCsH5)z synthesized according to a known method
Bisphenoxysilicon phthalocyanine was deposited on a glass substrate to obtain a recording layer with a thickness of 60 nm. The spectral characteristics of this recording layer are shown in Figure 2. In other words, Figure 2 shows the relationship between reflectance and transmittance (%, vertical axis) and wavelength (nm, horizontal axis) of the bisphenoxysilicon naphthalocyanine vapor-deposited film. This is a graph showing. 1 is transmittance, 2 is reflectance (incidence angle 5°
) is shown. When this recording medium was irradiated with a 780 nm laser beam from the glass substrate side and the recording characteristics were evaluated, recording was possible at a linear velocity of 0.5 m, 7 seconds, and 7.5 mW. On the other hand, in order to evaluate the stability against regeneration deterioration,
Although 1 mW of readout light was repeatedly irradiated, no change in reflectance occurred even after 1 million repetitions.
〈実施例３〉
公知の方法に準じて合成した。Ｐｅ５ｉ（Ｏ５ｉ（Ｃ２
Ｈａ）ａ）ｚビス−（トリエチルシリルオキシ）−スズ
フタロシアニンを、ガラス基板上に蒸着し、分光特性を
測定した。第３図は、ビス−（トリエチルシリルオキシ
）−スズ−フタロシアニン蒸着膜の反射率及び透過率（
％、縦軸）と波長（ｎｍ。<Example 3> Synthesis was performed according to a known method. Pe5i(O5i(C2
Ha)a)zBis-(triethylsilyloxy)-tin phthalocyanine was deposited on a glass substrate and its spectral properties were measured. Figure 3 shows the reflectance and transmittance (
%, vertical axis) and wavelength (nm.
横軸）との関係を示すグラフである。第３図において、
１は透過率、２は反射率（入射角５°）を示す。この記
録媒体に波長７８０ｎｍのレーザー光をガラス基板側か
ら照射し、記録特性を評価したところ、線速度０．５
ｍ／ｓ、５．４ ｍＷで記録が可能であった。一方、
再生劣化に対する安定性を評価するべく、１ｍＷの読み
出し光を繰り返し照射したが、百万回繰り返しても反射
率変化が生じなかった。It is a graph showing the relationship with the horizontal axis). In Figure 3,
1 indicates transmittance, and 2 indicates reflectance (incident angle 5°). When this recording medium was irradiated with a laser beam with a wavelength of 780 nm from the glass substrate side and the recording characteristics were evaluated, the linear velocity was 0.5.
Recording was possible at m/s and 5.4 mW. on the other hand,
In order to evaluate stability against reproduction deterioration, 1 mW readout light was repeatedly irradiated, but no change in reflectance occurred even after 1 million repetitions.
〈実施例４〉
公知の方法に準じて合成した（ｔ−Ｂｕ）ａＰｃＳｎ
（Ｏ５ｉ−（ＣｓＨｔｓ）ａ）ｚ、ビス（トリへキシル
シリルオキシ）スズ−テトラトラキス（ｔ−ブチル）フ
タロシアニン及び（ｔ−Ｂｕ）４ＰｃＧｅ（Ｏ５ｉ（Ｃ
＋Ｈｅ）ｓ）ｔ 、ビス（トリブチルシリルオキシ）ゲ
ルマニウム−テトラキシ（ｔ−ブチル）フタロシアニン
をクロロホルムに溶解し、スピンコード法にて、ガラス
基板上、厚さ５０ｎ＠の記録層を得た。この記録媒体に
実施例３と同様にしてレーザー光を照射したところ、そ
れぞれ４．８ ｍＷ及び５．２ ｍＷで記録が可能であ
った。また、再生劣化に対する安定性を同様に評価した
ところ、百万回繰り返しても反射率変化が生じなかった
。<Example 4> (t-Bu)aPcSn synthesized according to a known method
(O5i-(CsHts)a)z, bis(trihexylsilyloxy)tin-tetrakis(t-butyl)phthalocyanine and (t-Bu)4PcGe(O5i(C
+He)s)t , bis(tributylsilyloxy)germanium-tetraxy(t-butyl)phthalocyanine was dissolved in chloroform, and a recording layer with a thickness of 50 n@ was obtained on a glass substrate by a spin code method. When this recording medium was irradiated with laser light in the same manner as in Example 3, recording was possible at 4.8 mW and 5.2 mW, respectively. Furthermore, when the stability against playback deterioration was evaluated in the same manner, no change in reflectance occurred even after repeating one million times.
く比較例〉
公知の方法に準じて合成したテトラ（ｔ−ブチル）バナ
ジルフタロシアニンＶＯＰｃ（ｔ−Ｂｕ）番をトルエン
に溶解し、スピンコード法でガラス基板上に４５ｎ＋ｗ
の薄膜を形成した。第４図は、この薄膜の透過率、及び
、反射率（％、縦軸）と波長（止。Comparative Example> Tetra(t-butyl)vanadyl phthalocyanine VOPc (t-Bu) synthesized according to a known method was dissolved in toluene, and 45n+w was placed on a glass substrate using a spin code method.
A thin film was formed. Figure 4 shows the transmittance and reflectance (%, vertical axis) and wavelength (stop) of this thin film.
横軸）との関係を示すグラフであり、反射率はたかだか
１６〜７％であることがわかる。１は透過率、２は反射
率（入射角５°）を示す。It is a graph showing the relationship with the horizontal axis), and it can be seen that the reflectance is at most 16 to 7%. 1 indicates transmittance, and 2 indicates reflectance (incident angle 5°).
本発明の光学的情報記録媒体は、高反射率であり、かつ
、優れた記録再生特性をもつ。The optical information recording medium of the present invention has high reflectance and excellent recording and reproducing characteristics.
第１図は本発明の一実施例のビス−（トリフェニルシリ
ルオキシ）−シリコンフタロシアニン蒸着膜の反射率及
び透過率の波長依存性を示すグラフ、第２図、第３図は
それぞれビスフェノキシシリコンナフタロシアニン蒸着
膜、ビス−（トリエチルシリルオキシ）−入ズフタロシ
アニン蒸着膜の反射率及び透過率の波長依存性を示すグ
ラフ、第４図はテトラ（ｔ−ブチル）バナジルフタロシ
アニン塗布膜の反射率及び透過率の波長依存性を示すグ
ラフである。
第１図
沢 畏（）ｔカ７ノ
第２図
１足長（匁ワη、ン
盪五七反訂午（γ・〕FIG. 1 is a graph showing the wavelength dependence of the reflectance and transmittance of a bis-(triphenylsilyloxy)-silicon phthalocyanine vapor-deposited film according to an embodiment of the present invention, and FIGS. A graph showing the wavelength dependence of the reflectance and transmittance of the naphthalocyanine vapor-deposited film and the bis-(triethylsilyloxy)-containing diphthalocyanine vapor-deposited film. It is a graph showing wavelength dependence of transmittance. Figure 1 Sawa wo ()tka7ノ Figure 2 1 Foot length (monme wa η, ng 57 tai sho (γ・)
Claims (1)
アニン系色素を主成分とする有機薄膜が形成されている
ことを特徴とする光学的情報記録媒体。 ▲数式、化学式、表等があります▼ …〔 I 〕 ［式中、Ｒ＿１〜Ｒ＿４は、同一、又は、異なり、直鎖
、または、分岐アルキル基、アルコキシ基、ハロゲンよ
りなる群より選ばれ、ｎは同一、又は、異なり、０〜４
の整数、Ｙ＿１及びＹ＿２は同一、又は、異なり、Ｒ、
−Ａｒ、−ＯＲ、 −ＯＡｒ、−ＯＳｉ（Ｒ）＿３、ＯＳｉＡｒ＿３よりな
る群から選択した基（ただし、ＲはＣ＿１〜Ｃ＿１＿８
の直鎖、または、分岐アルキル基、Ａｒはフェニル基、
置換フェニル基よりなる群から選択した基である）を示
し、ＭはＡｌ、Ｓｉ、Ｇｅ、Ｓｎよりなる群より選択さ
れた元素を示す、ただし、ＭがＡｌの時は、Ｙ＿１のみ
がＭに結合しているものとする。］ ２、前記一般式［ I ］におけるＹ＿１及びＹ＿２が共
に−ＯＳｉ（Ｒ＿３）又は−ＯＳｉ（Ａｒ＿３）である
ことを特徴とする特許請求の範囲第１項記載の光学的情
報記録媒体。 ３、前記一般式［ I ］における、ｎが０であるか、あ
るいはＲ＿１〜Ｒ＿４が、第三ブチル基、又は、塩素で
あることを特徴とする特許請求の範囲第１項または第２
項に記載の光学的情報記録媒体。 ４、光反射膜を用いないタイプの光記録媒体であり、前
記基板上に一般式［ I ］で示されるナフタロシアニン
系色素を主成分とする有機薄膜を形成したことを特徴と
する特許請求の範囲第１項、第２項または第３項記載の
光学的情報記録媒体。[Claims] 1. An optical information recording medium characterized in that an organic thin film containing a phthalocyanine dye represented by the following general formula [I] as a main component is formed on a substrate. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ … [I] [In the formula, R_1 to R_4 are the same or different, and are selected from the group consisting of a straight chain or branched alkyl group, alkoxy group, and halogen, and n are the same or different, 0 to 4
integers, Y_1 and Y_2 are the same or different, R,
-Ar, -OR, -OAr, -OSi(R)_3, OSiAr_3 (where R is C_1 to C_1_8
A straight chain or branched alkyl group, Ar is a phenyl group,
is a group selected from the group consisting of substituted phenyl groups), and M is an element selected from the group consisting of Al, Si, Ge, and Sn. However, when M is Al, only Y_1 is M. Assume that they are connected. 2. The optical information recording medium according to claim 1, wherein Y_1 and Y_2 in the general formula [I] are both -OSi(R_3) or -OSi(Ar_3). 3. Claims 1 or 2, characterized in that in the general formula [I], n is 0, or R_1 to R_4 are a tert-butyl group or chlorine.
The optical information recording medium described in . 4. An optical recording medium of a type that does not use a light reflective film, characterized in that an organic thin film containing a naphthalocyanine dye represented by the general formula [I] as a main component is formed on the substrate. Optical information recording medium according to scope 1, 2, or 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62300249A JPH01141795A (en) | 1987-11-30 | 1987-11-30 | Optical information recording medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62300249A JPH01141795A (en) | 1987-11-30 | 1987-11-30 | Optical information recording medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01141795A true JPH01141795A (en) | 1989-06-02 |
Family
ID=17882507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62300249A Pending JPH01141795A (en) | 1987-11-30 | 1987-11-30 | Optical information recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01141795A (en) |
Cited By (5)
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|---|---|---|---|---|
| WO2006015410A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Metal-cyanine dye having axial ligands which reduce visible absorption |
| WO2006015409A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Metal-cyanine dye having improved water solubility |
| WO2006015408A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Cyanine dye having reduced visible absorption |
| WO2006015407A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Method of minimizing absorption of visible light in infrared dyes |
| WO2006015413A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Synthesis of metal cyanines |
-
1987
- 1987-11-30 JP JP62300249A patent/JPH01141795A/en active Pending
Cited By (18)
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|---|---|---|---|---|
| WO2006015410A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Metal-cyanine dye having axial ligands which reduce visible absorption |
| WO2006015409A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Metal-cyanine dye having improved water solubility |
| WO2006015408A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Cyanine dye having reduced visible absorption |
| WO2006015407A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Method of minimizing absorption of visible light in infrared dyes |
| WO2006015413A1 (en) * | 2004-08-09 | 2006-02-16 | Silverbrook Research Pty Ltd | Synthesis of metal cyanines |
| US7278727B2 (en) | 2004-08-09 | 2007-10-09 | Silverbrook Research Pty Ltd | Method of minimizing absorption of visible light in infrared dyes |
| US7367665B2 (en) | 2004-08-09 | 2008-05-06 | Silverbrook Research Pty Ltd | Metal-cyanine dye having axial ligands which reduce visible absorption |
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| US7550585B2 (en) | 2004-08-09 | 2009-06-23 | Silverbrook Research Pty Ltd | Synthesis of metal cyanines |
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| US7834175B2 (en) | 2004-08-09 | 2010-11-16 | Silverbrook Research Pty Ltd | Method of preparing macrocylic metal cyanine compound |
| US7891772B2 (en) | 2004-08-09 | 2011-02-22 | Silverbrook Research Pty Ltd | Pagewidth printhead unit |
| US7946626B2 (en) | 2004-08-09 | 2011-05-24 | Silverbrook Research Pty Ltd | Substrate having IR-absorbing dye with branched axial ligands |
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| US7997718B2 (en) | 2004-08-09 | 2011-08-16 | Silverbrook Research Pty Ltd | Substrate having dye with dendrimer axial ligands disposed thereon |
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