JPS6372594A - Optical information recording medium - Google Patents
Optical information recording mediumInfo
- Publication number
- JPS6372594A JPS6372594A JP61215928A JP21592886A JPS6372594A JP S6372594 A JPS6372594 A JP S6372594A JP 61215928 A JP61215928 A JP 61215928A JP 21592886 A JP21592886 A JP 21592886A JP S6372594 A JPS6372594 A JP S6372594A
- Authority
- JP
- Japan
- Prior art keywords
- group
- recording medium
- information recording
- optical information
- dye
- 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.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 20
- 239000000758 substrate Substances 0.000 claims abstract description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 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 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 239000010703 silicon Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000008929 regeneration Effects 0.000 abstract description 3
- 238000011069 regeneration method Methods 0.000 abstract description 3
- 239000010410 layer Substances 0.000 abstract 2
- 239000012528 membrane Substances 0.000 abstract 2
- 230000002542 deteriorative effect Effects 0.000 abstract 1
- 239000011241 protective layer Substances 0.000 abstract 1
- -1 naphthalocyanine compound Chemical class 0.000 description 20
- 239000000975 dye Substances 0.000 description 17
- 230000006866 deterioration Effects 0.000 description 11
- 239000011521 glass Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000620 organic polymer Chemical class 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910019443 NaSi Inorganic materials 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000005540 biological transmission 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
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical group COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 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
- 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000004065 semiconductor Substances 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
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 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
Landscapes
- Thermal Transfer Or Thermal Recording In General (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
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
膜を有する光学的情報記録媒体に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an optical information recording medium, particularly an optical information recording medium having an organic thin film containing a dye.
更に詳しくは、レーザービームにより直接記録し、反射
率の変化により情報再生を行う方法に用いられる光学的
情報記録媒体に関する。More specifically, the present invention relates to an optical information recording medium used in a method of directly recording with a laser beam and reproducing information by changing reflectance.
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が行われている。2. Description of the Related Art Optical information recording media have the characteristic that the recording medium does not deteriorate due to wear and tear because the medium and the recording or reproducing head are not in contact with each other, and various research and development efforts are being carried out on the development of various recording media.
特にヒートモード記録方式の分野においては、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、融解ないし昇華温度が低いため、記録感民の点で
好ましく、シアニン色素、スクワリクム色素など種々の
物質が提案されている。Particularly in the field of heat mode recording methods, low melting point metals, organic polymer compounds, or dyes have been proposed as materials that melt, evaporate, or sublimate.Among them, organic thin films containing organic polymer compounds and dyes have a high thermal conductivity. is small,
Further, since the melting or sublimation temperature is low, it is preferable from the viewpoint of recording sensitivity, and various substances such as cyanine dyes and squaricum dyes have been proposed.
従来、色素を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 using a dye as a recording layer is known from, for example, Japanese Patent Laid-Open No. 16948/1983.
しかしながら、この糧の色素薄膜記録層を反射型の光学
的情報記録媒体として利用するためには金属反射膜全必
要とし、そのために媒体構成が複雑になった夛、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＠しかしながら、シアニン系色素は一般に耐光
性が低いため、！き込み後の読み出しの際、読み出し尤
の繰返し照射によって色素が脱色し、読み出しの８７Ｎ
比が低下してしまうという、いわゆる再生劣化が大きい
という問題がある。一方、灯光堅ろう性の優れた色素と
してナフタロシアエン化合物を記録層に用いることが特
開昭６１−２５８８６号公報により提案されている０〔
発明が解決しようとする問題点〕
しかしながら、ナフタロシアエン化合物の反射率は一般
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, in order to use this basic dye thin film recording layer as a reflective optical information recording medium, an entire metal reflective film is required, which results in a complicated media structure and poor information recording and reproducing characteristics. There is a problem. On the other hand, it has been proposed in JP-A-60-78787 to use cyanine dyes, etc., which have a moderately high reflectance of the dye itself. ! During readout after writing, the dye is bleached due to repeated irradiation during readout, and 87N of readout
There is a problem in that the ratio decreases, that is, so-called reproduction deterioration is large. On the other hand, JP-A-61-25886 proposes the use of naphthalocyanene compounds as dyes with excellent light fastness in the recording layer.
Problems to be Solved by the Invention] However, the reflectance of naphthalocyanene compounds is generally lower than that of cyanine dyes, and they are 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有すると共に、
改善された再生劣化特性を有する光学的情報記録媒体を
提供することにある。The object of the present invention is to have excellent recording and reproducing characteristics, and
An object of the present invention is to provide an optical information recording medium having improved reproduction deterioration characteristics.
本発明を概説すれば、本発明は光学的情報記録媒体に関
する発明であって、基板上に下記一般式ｌで表されるナ
フタロシアエ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０〔式中、Ｒ１−Ｒ４は同−
又は異なり、直鎖若しくは分岐アルキル基又はハロゲン
、ｎｉ：を同−又は異なり、０〜６の整数、Ｙｌ及びＹ
、は同−又は異なり、−Ｒ、−Ａｒ 、 −ＯＲ、−０
Ａｒ 、 −０８１（Ｒ）１、−０８ｉＡｒ３、−０８
１（ＯＲ）ｓ、−０８１（ＯＡｒ）１ 及び−ＱＣ（Ｃ
ｓＨｓ）ｓよりなる群から選択した基（ただしＲはＣ１
〜ｅｔａの直鎖又は分岐アルキル基、Ａｒはフェニル基
、置換フェニル基、ベンジル基及び置換ベンジル基より
なる群から選択した基である）′＠：示す〕
不発明は、既述の従来技術の状況にかんがみてなされた
ものであり、前記した従来の欠点を改良するべく鋭意検
討の結果、ある種のナフタロシアエン化合物を用いた場
合、シアニン系色素と同等又はそれ以上の反射率ヲ有し
、かつ再生劣化特性が優れていることを見出し、本発明
を光取するに到った。To summarize the present invention, the present invention relates to an optical information recording medium, in which an organic thin film containing a naphthalocyanene dye represented by the following general formula 1 as a main component is formed on a substrate. 0 [wherein R1-R4 are the same -
or different, straight chain or branched alkyl group or halogen, ni: the same or different, an integer of 0 to 6, Yl and Y
, are the same or different, -R, -Ar, -OR, -0
Ar, -081(R)1, -08iAr3, -08
1(OR)s, -081(OAr)1 and -QC(C
sHs) a group selected from the group consisting of s (where R is C1
~eta is a straight chain or branched alkyl group, Ar is a group selected from the group consisting of a phenyl group, a substituted phenyl group, a benzyl group, and a substituted benzyl group)'@: indicates] This was done in view of the current situation, and as a result of intensive studies to improve the conventional drawbacks mentioned above, it was found that when a certain naphthalocyanine compound is used, it has a reflectance equal to or higher than that of cyanine dyes. , and excellent regeneration and deterioration characteristics, leading to the invention of the present invention.
本発明の光学的情報記録媒体は、基板上に本発明の上記
ナツタ關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腹層などの他の
層を設けることができる０本発明において使用される基
板材料は当業者には既知のものであり、使用レーザー元
に対して透明又は不透明のいずれでも良い。しかし、基
板側から、レーザー元で書き込み、読み出しを行う場合
は、レーザー元に対して透明でなければならない。一方
、基板と反対側すなわち記録層側から書き込み、読み出
しを行う場合は、レーザー元に対して透明である必要は
ない◇基板の材質としては、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０本発明の前記一般式（１）において、Ｒ１〜＆の例
としては、メチル基、エチル基、プロピル基、インプロ
ピル基、ｎ−ブチル基、ｔ−ブチル基、ｎ−ペンチル基
、８−アミル基、ｔ−アミル基、１−ヘプチル基、ｔ−
オクチル基、七−ドデシル基、塩素、臭素、フッ素など
がある。Ｙ、及びＹ、の例としては、メチル基、エチル
基、メトキシ基、メトキシ基、ペントキシ基、オクトキ
シ基、フェノキシ基、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）シリルオ
キシ基、トリフェニルメチルオキシ基、トリメトキシシ
リルオキシ基、トリフエノキシシリルオキシ基、ｎ−オ
クチル基、ｎ−オクタデシル基、ベンジルオキシ基、ｐ
−メチルフェニル基％Ｐ−メトキシフェニル基、ベンジ
ル基、ｐ−メチルベｙ−）ル基、ｐ−メチルフェニルオ
キシＭ、ｐ −）チルベンジルオキシ基、トリ（ｐ−メ
チルフェニル）シリルオキシ基、トリ（ｐ−メチルベン
ジル）シリルオキシ基、トリベンジルシリルオキシ基、
トリ（ｐ−メチルフェノキシ）シリルオキシ基、トリ（
ｐ−メチルベンジルオキシ）シリルオキシ基などが挙げ
られる。The optical information recording medium of the present invention has a recording layer containing the above-mentioned cyanine dye of the present invention as a main component on a substrate. The substrate materials used in the present invention are known to those skilled in the art and can be either transparent or opaque to the laser source used. However, when writing and reading from the substrate side using a laser source, it must be transparent to the laser source. On the other hand, when writing or reading from the side opposite to the substrate, that is, from the recording layer side, it does not need to be transparent to the laser source ◇ The material of the substrate may be glass, quartz, ceramic, plastic, paper, plate, or A commonly used support for recording materials, such as a metal foil, may be used. In addition, the substrate may be provided with a guide groove formed of unevenness if necessary. In the general formula (1) of the present invention, examples of R1 to & include a methyl group, an ethyl group, and a propyl group. , inpropyl group, n-butyl group, t-butyl group, n-pentyl group, 8-amyl group, t-amyl group, 1-heptyl group, t-
Examples include octyl group, 7-dodecyl group, chlorine, bromine, and fluorine. Examples of Y and Y include methyl group, ethyl group, methoxy group, methoxy group, pentoxy group, octoxy group, phenoxy group, octadecyloxy group, trimethylsilyloxy group, triethylsilyloxy group, triphenylsilyloxy group, Tri(n-hexyl)silyloxy group, triphenylmethyloxy group, trimethoxysilyloxy group, triphenoxysilyloxy group, n-octyl group, n-octadecyl group, benzyloxy group, p
-Methylphenyl group% P-methoxyphenyl group, benzyl group, p-methylbey-)yl group, p-methylphenyloxy M, p-)thylbenzyloxy group, tri(p-methylphenyl)silyloxy group, tri( p-methylbenzyl)silyloxy group, tribenzylsilyloxy group,
Tri(p-methylphenoxy)silyloxy group, tri(
Examples include p-methylbenzyloxy)silyloxy group.
また、本発明において使用されるす７り゛ロシアニン化
合物の例としては以下のものを挙げることができる。Moreover, the following can be mentioned as an example of the 7-lycyanine compound used in the present invention.
（１１Ｎｃｓｔ（ｏｓｌ（ｎ−ｃｓＨｔｓ）ｓ”ｌ＊ビ
ス−（トリへキシルシリルオキシ）−す７タロシアニノ
ーシリコン
上記式において、ＮＣはナフタロシアエン骨格を表す（
以下同じ。）
（２１Ｎａ８１（Ｏ８ｉ（ＣＨｓ）３）！ビスー（トリ
メチルシリルオキシ）−ナフタロシアニノーシリコン
（３１ＮｃＳｉ（Ｏ８ｉ（Ｃ２Ｈｇ）１）１ビス−（ト
リエチルシリルオキシ）−ナフタロシアニノーシリーン
（４１ＮｃＳｉ（ＯＣｘＨ＠）ｓ
ビスエトキシーナフタロシアニノーシリコン（５） Ｎ
ａ８１（ＯＣｓＨ■）ｓ
ビス（アミルオキシ）ナフタロシアニノシリコン
（ｅ） ＮｃＳｉ、（ＯＣ＠Ｉｓ）鵞ビス（フェニ
ルオキシ）ナフタロシアニノシリコン
（７） ＮｃＳｉ（０８１（Ｃ番Ｈｓ）ｓ）富ビス
ートリフェニルシリルオキシーナフタロシアニノーシリ
コン
（ｇ） Ｎａ８１（ＣｓＨｓ）＊
ビスフェニルーナフタロシアニノーシリコン（９）
ＮａＳｉ （ＱＣ＠Ｈ１ｙ ）１ビス（オクトキシ）−
ナフタロシアニノーシリコン
０１３ Ｎｏ（ｔ−Ｂｕ）４８１（０（Ｃ＠Ｈｔｓ
）ｘ）＊ビスー（トリへキシルシリルオキシ）−テトラ
−１−プチルナフタロシアニノーシリコン（ロ） Ｎｃ
Ｓｉ（ＯＣＨｓ）ｘ
ビスメトキシナフタロシアニノシリコンＨＮ０８ｉ（Ｑ
Ｃ（（４Ｈ５）３〕２
ビス−（トリフェニルメチルオキシ）−ナフタロシアニ
ノシリコン
これらのナフタロシアエン化合物は、ジャーナル・オブ
・アメリカン・ケミカル・ンサイエテイ−（Ｊ、Ａｍｅ
ｒ、 Ｃｈｅｍ、 ８ｏｃ、 ） １９８４年、１０６
巻、第７４０４頁から第７４１０頁等に記載される公知
の方法で製造し得る〇
本発明における記録層の形成は、ｉ邪法ないし蒸着法に
おいて行うことができる。塗布法を用いル場合にハ、ト
ルエン、クロロホルム、ジクロロエタン、メチルエチル
ケトンなどの溶媒を用いてスプレー、ローラーコーティ
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。(11Ncst(osl(n-csHts)s"l*bis-(trihexylsilyloxy)-su7talocyaninosilicon In the above formula, NC represents a naphthalocyanine skeleton (
same as below. ) (21Na81(O8i(CHs)3)!Bis-(trimethylsilyloxy)-naphthalocyaninosilicon(31NcSi(O8i(C2Hg)1)1bis-(triethylsilyloxy)-naphthalocyaninosilicon(41NcSi(OCxH@)s Bisethoxynaphthalocyanino silicone (5) N
a81(OCsH■)s Bis(amyloxy)naphthalocyaninosilicon (e) NcSi, (OC@Is) Bis(phenyloxy)naphthalocyaninosilicon(7) NcSi(081(C number Hs)s) Rich bistri Phenylsilyloxynaphthalocyaninosilicon (g) Na81 (CsHs)* Bisphenylnaphthalocyaninosilicon (9)
NaSi (QC@H1y)1bis(octoxy)-
Naphthalocyanino silicon 013 No (t-Bu) 481 (0 (C@Hts
) x) *Bis(trihexylsilyloxy)-tetra-1-butylnaphthalocyaninosilicon (b) Nc
Si (OCHs) x Bismethoxy naphthalocyanino silicon HN08i (Q
C((4H5)3]2 Bis-(triphenylmethyloxy)-naphthalocyaninosilicon
r, Chem, 8oc, ) 1984, 106
The recording layer according to the present invention can be formed by a conventional method or a vapor deposition method. When a coating method is used, spraying, roller coating, spin coating, dipping, etc. are performed using a solvent such as toluene, chloroform, dichloroethane, or methyl ethyl ketone.
本発明は、レーザー元の波長域に適度の吸収率及び反射
ａｔ示し、かつ、耐光性の優れた特定のナフタロシアエ
ン化合物を主成分とする有機薄膜全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 a specific naphthalocyanene compound as a main component, which exhibits appropriate absorption and reflection at in the wavelength range of the laser source, and has excellent light resistance, as the entire recording layer. It has both excellent recording and reproduction characteristics and improved reproduction deterioration characteristics.
以下、本発明の具体的実施例を示し、本発Ｆ！Ａを更に
詳細に説明するが、本発明はこれらに限定されるもので
はない。Hereinafter, specific examples of the present invention will be shown, and the F! A will be explained in more detail, but the present invention is not limited thereto.
実施例１
先に例示したＮｃＳｉ（Ｏ８ｉ（ｎ−Ｃ＠Ｈ１ｓ ）ｓ
：］］ｚビスートｙ−ｎ−へキシルシリルオキシ）−ナ
フタロシアエノーシリー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５０ｎｍの記録層を得た
〇°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−（トリーｎ−へキシルシリルオキシ）−ナ
フタロシアノ−シリコン蒸着膜の反射率△
及び透過＊（％、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
８５０ｎｍの半導体レーザーをガラス基板側から照射し
、記録特性を評価したところ、ビーム径ｔ６μｍ１線速
α５ ｍ ７秒、４．４シ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、１シの読み
出し元を繰返し照射したが、１０６回繰返しても反射率
変化が生じなかった。Example 1 The previously exemplified NcSi(O8i(n-C@H1s)s
:]]ZBistoy-n-hexylsilyloxy)-naphthalocyanenosilene was synthesized according to a known method and deposited on a glass substrate to obtain a recording layer with a thickness of 50 nm〇〇This recording layer Fig. 1 shows the spectral characteristics of . In other words, Figure 1 is a graph showing the relationship between reflectance △ and transmission* (%, vertical axis) and wavelength (nm, horizontal axis) of a bis-(tri-n-hexylsilyloxy)-naphthalocyano-silicon deposited film. be. In Figure 1, 1 is transmittance, 2
indicates the reflectance (incident angle 5''). When this recording medium was irradiated with a semiconductor laser with a wavelength of 850 nm from the glass substrate side and the recording characteristics were evaluated, it was found that the beam diameter was 6 μm, the linear velocity was α5 m, 7 seconds, and 4.4 On the other hand, in order to evaluate the stability against reproduction deterioration, the readout source of 1 shi was repeatedly irradiated, but no change in reflectance occurred even after 106 repetitions.
比較例１
シアニン系色素ＮＫ−２９０５（日本感光色素研究所！
Ｉｌ）をジクロロエタンに溶解し、回転塗布により１．
ガラス基板上、厚さ５０ｎｍの記録層ｔ″得た。この記
録媒体に実施例１と同様にしてレーザー元を照射したと
ころ、ｔａｍｗで記録が可能であった。しかし、再生劣
化に対する安定性を評価したところ、繰返し照射回数４
Ｘ １０４回付近から、反射率が低下しはじめ、１０
６回照射後では、初期反射率の７０％まで低下した。Comparative Example 1 Cyanine dye NK-2905 (Japan Photosensitive Color Research Institute!
1) by dissolving it in dichloroethane and spin coating.
A recording layer t'' with a thickness of 50 nm was obtained on a glass substrate. When this recording medium was irradiated with a laser source in the same manner as in Example 1, recording was possible at tamw. However, stability against reproduction deterioration was When evaluated, the number of repeated irradiations was 4.
The reflectance starts to decrease from around 104 times, and 10
After irradiation six times, the reflectance decreased to 70% of the initial reflectance.
実施例２
公知の方法に準じて合成したビス−（） ！Ｊ −ｎ−
へキシルシリルオキシ）−テトラ−ｔａｒｔ−プチルナ
フタロシアニノーシリコンＮｃ（ｔ−Ｂｕ）４Ｓｉ（Ｏ
８ｉ（ｎ−Ｃ’ａＨｔｓ）ｉ）ｘ ’にクロロホルムに
溶解し、回転塗布法により、ガラス基板上、厚さ６０ｎ
ｍの記録層を得た。この記録媒体（実施例１と同様にし
てレーザー元を照射したところ、１２ｍＷ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、１０６回繰返し照射しても反射率変化が生
じなかった。Example 2 Bis-() ! synthesized according to a known method. J-n-
hexylsilyloxy)-tetra-tart-butylnaphthalocyaninosilicon Nc(t-Bu)4Si(O
8i(n-C'aHts)i)x' was dissolved in chloroform and coated on a glass substrate to a thickness of 60 nm by spin coating.
A recording layer of m was obtained. When this recording medium was irradiated with a laser source in the same manner as in Example 1, recording was possible at 12 mW.Furthermore, when stability against playback deterioration was evaluated in the same way, the reflectance remained even after repeated irradiation 106 times. No change occurred.
実施例３
公知の方法に準じて合成したとスフエノキシナフタロシ
ア二ノシリコンをガラス基板上、蒸着法にて、厚さ７０
ｎｍの記録膜を得た。この記録媒体に実施例１と同様に
してレーザー元を照射したとＣろ、５．５ｍＷ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、１０６回繰返し照射しても反射率変
化が生じなかつ次。Example 3 Suphenoxynaphthalocyaninosilicon synthesized according to a known method was deposited on a glass substrate to a thickness of 70 mm by vapor deposition.
A recording film of nm size was obtained. When this recording medium was irradiated with a laser source in the same manner as in Example 1, recording was possible at 5.5 mW. In addition, when the stability against reproduction deterioration was similarly evaluated, no change in reflectance occurred even after repeated irradiation 106 times.
実施例４
下表に示したナツタｎシアニン系色素をポリカーボネー
ト基板上、５０ｎｍの厚さの記録ＦＪを蒸着法にて形成
した。実施例１と同様にして記録再生特性、再生劣化特
９：全評価し念。結果を下記表１に掲げる。Example 4 A recording FJ having a thickness of 50 nm was formed using the Natsuta n-cyanine dye shown in the table below on a polycarbonate substrate by vapor deposition. Recording/reproduction characteristics and reproduction deterioration characteristics 9: All evaluations were carried out in the same manner as in Example 1. The results are listed in Table 1 below.
表 １
実施例５
Ｎｃ８１（０８１（ｎ−Ｃ＠Ｈｔｓ ）ｓ）ｚとポリス
チレンの２二１混合物をメチルエチルケトンに溶解し、
ガラス基板上、厚さ８０ｎｍの記録層を得た。実施例１
と同様にして評価したところ、記録感度５．３ｍＷ、再
生劣化１０６回以上という結果を得た。Table 1 Example 5 A 221 mixture of Nc81(081(n-C@Hts)s)z and polystyrene was dissolved in methyl ethyl ketone,
A recording layer with a thickness of 80 nm was obtained on a glass substrate. Example 1
When evaluated in the same manner as above, the results were that the recording sensitivity was 5.3 mW and the reproduction deterioration was 106 times or more.
以上説明したように、本発明の光学的情報記録媒体は、
優れた記録再生特性を示し、かつ、従来の有機色素系記
録媒体より再生劣化特性が同上するという顕著な効果を
奏するものである０As explained above, the optical information recording medium of the present invention includes:
It exhibits excellent recording and reproducing characteristics, and has the remarkable effect of having the same reproduction deterioration characteristics as described above compared to conventional organic dye-based recording media.
第１図は、ビス−（トリーｎ−へキシルシリルオキシ）
−ナフタロシアニノーシリコ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である。Figure 1 shows bis-(tri-n-hexylsilyloxy)
- It is a graph showing the wavelength dependence of the reflectance and transmittance of a naphthalocyanino-silicon vapor deposited film.
Claims (1)
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、直鎖若しく
は分岐アルキル基又はハロゲン、ｎは同一又は異なり、
０〜６０整数、Ｙ＿１及びＹ＿２は同一又は異なり、−
Ｒ、−Ａｒ、−ＯＲ、−ＯＡｒ、−ＯＳｉ（Ｒ）＿３、
ＯＳｉＡｒ＿ｓ、−ＯＳｉ（ＯＲ）＿３、−ＯＳｉ（Ｏ
Ａｒ）＿３及び−ＯＣ（Ｃ＿６Ｈ＿６）＿２よりなる群
から選択した基（ただしＲはＣ＿１〜Ｃ＿１＿■の直鎖
又は分岐アルキル基、Ａｒはフェニル基、置換フェニル
基、ベンジル基及び置換ベンジル基よりなる群から選択
した基である）を示す〕 ２、前記一般式 I におけるＹ＿１重及びＹ＿２が、共
に−ＯＲ又は−ＯＡｒ基であ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Ｙ＿１及びＹ＿２が、共に
−ＯＳｉ（Ｒ）＿３又は−ＯＳｉＡｒ＿２である特許請
求の範囲第１項記載の光学的情報記録媒体。 ４、前記一般式 I において、ｎが０であるか、あるい
はＲ＿１〜Ｒ＿４が、第３ブチル基又は塩素である特許
請求の範囲第１項〜第３項のいずれか１項に記載の光学
的情報記録媒体。 ５、該ナフタロシアエン系色素が、ビス−（トリヘキシ
ルシリルオキシ）−ナフタロシアニノ−シリコンである
特許請求の範囲第１項記載の光学的情報記録媒体。 ６、該ナフタロシアエン系色素が、ビス−（トリヘキシ
ルシリルオキシ）−テトラ−ｔｅｒｔ−プチルナフタロ
シアニノ−シリコンである特許請求の範囲第１項記載の
光学的情報記録媒体。 ７、該ナフタロシアエン系色素が、ビスフエノキシ−ナ
フタロシアエノ−シリコンである特許請求の範囲第１項
記載の光学的情報記録媒体。 ８、該ナフタロシアエン系色素が、ビスメトキシーナフ
タロシアニノ−シリコンである特許請求の範囲第１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 naphthalocyanene 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, linear or branched alkyl groups or halogens, n is the same or different,
0 to 60 integer, Y_1 and Y_2 are the same or different, -
R, -Ar, -OR, -OAr, -OSi(R)_3,
OSiAr_s, -OSi(OR)_3, -OSi(O
A group selected from the group consisting of Ar)_3 and -OC(C_6H_6)_2 (where R is a linear or branched alkyl group of C_1 to C_1_■, Ar is a phenyl group, a substituted phenyl group, a benzyl group, and a substituted benzyl group) 2. The optical information recording medium according to claim 1, wherein Y_1 and Y_2 in the general formula I are both -OR or -OAr groups. 3. 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 -OSiAr_2. 4. The optical compound according to any one of claims 1 to 3, wherein in the general formula I, n is 0, or R_1 to R_4 are a tertiary butyl group or chlorine. Information recording medium. 5. The optical information recording medium according to claim 1, wherein the naphthalocyanine dye is bis-(trihexylsilyloxy)-naphthalocyanino-silicon. 6. The optical information recording medium according to claim 1, wherein the naphthalocyanine dye is bis-(trihexylsilyloxy)-tetra-tert-butylnaphthalocyanino-silicon. 7. The optical information recording medium according to claim 1, wherein the naphthalocyanene dye is bisphenoxy-naphthalocyaneno-silicon. 8. The optical information recording medium according to claim 1, wherein the naphthalocyanine dye is bismethoxynaphthalocyanino-silicon.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61215928A JPH0745259B2 (en) | 1986-09-16 | 1986-09-16 | Optical information recording medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61215928A JPH0745259B2 (en) | 1986-09-16 | 1986-09-16 | Optical information recording medium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6372594A true JPS6372594A (en) | 1988-04-02 |
| JPH0745259B2 JPH0745259B2 (en) | 1995-05-17 |
Family
ID=16680580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61215928A Expired - Lifetime JPH0745259B2 (en) | 1986-09-16 | 1986-09-16 | Optical information recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0745259B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6394893A (en) * | 1986-10-09 | 1988-04-25 | Kao Corp | Optical information recording medium |
| EP0381211A2 (en) * | 1989-02-01 | 1990-08-08 | Mitsui Petrochemical Industries, Ltd. | Optical recording media |
| JPH0379683A (en) * | 1989-08-22 | 1991-04-04 | Toyo Ink Mfg Co Ltd | Near infrared-absorbing ink, heat-sensitive transfer material and detecting method |
| US5064951A (en) * | 1989-04-06 | 1991-11-12 | Orient Chemical Industries, Ltd. | Naphthalocyanine compound and production thereof |
| US5149847A (en) * | 1989-04-06 | 1992-09-22 | Orient Chemical Industries, Ltd. | Naphthalocyanine compound and production thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61177288A (en) * | 1985-02-04 | 1986-08-08 | ヘキスト・セラニーズ・コーポレーション | Optical information record medium containing organic large ring chromophore |
| JPS61177287A (en) * | 1985-02-04 | 1986-08-08 | ヘキスト・セラニーズ・コーポレーション | Information record medium containing chromophore |
| JPS6239286A (en) * | 1985-08-13 | 1987-02-20 | Mitsubishi Chem Ind Ltd | Optical recording material |
-
1986
- 1986-09-16 JP JP61215928A patent/JPH0745259B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61177288A (en) * | 1985-02-04 | 1986-08-08 | ヘキスト・セラニーズ・コーポレーション | Optical information record medium containing organic large ring chromophore |
| JPS61177287A (en) * | 1985-02-04 | 1986-08-08 | ヘキスト・セラニーズ・コーポレーション | Information record medium containing chromophore |
| JPS6239286A (en) * | 1985-08-13 | 1987-02-20 | Mitsubishi Chem Ind Ltd | Optical recording material |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6394893A (en) * | 1986-10-09 | 1988-04-25 | Kao Corp | Optical information recording medium |
| EP0381211A2 (en) * | 1989-02-01 | 1990-08-08 | Mitsui Petrochemical Industries, Ltd. | Optical recording media |
| US5064951A (en) * | 1989-04-06 | 1991-11-12 | Orient Chemical Industries, Ltd. | Naphthalocyanine compound and production thereof |
| US5149847A (en) * | 1989-04-06 | 1992-09-22 | Orient Chemical Industries, Ltd. | Naphthalocyanine compound and production thereof |
| JPH0379683A (en) * | 1989-08-22 | 1991-04-04 | Toyo Ink Mfg Co Ltd | Near infrared-absorbing ink, heat-sensitive transfer material and detecting method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0745259B2 (en) | 1995-05-17 |
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