JPH0737580B2 - Chromium-containing azo compound and optical recording medium containing the same - Google Patents

Chromium-containing azo compound and optical recording medium containing the same

Info

Publication number
JPH0737580B2
JPH0737580B2 JP61223913A JP22391386A JPH0737580B2 JP H0737580 B2 JPH0737580 B2 JP H0737580B2 JP 61223913 A JP61223913 A JP 61223913A JP 22391386 A JP22391386 A JP 22391386A JP H0737580 B2 JPH0737580 B2 JP H0737580B2
Authority
JP
Japan
Prior art keywords
group
chromium
general formula
recording medium
azo compound
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.)
Expired - Lifetime
Application number
JP61223913A
Other languages
Japanese (ja)
Other versions
JPS6381165A (en
Inventor
修一 前田
裕 黒瀬
享代 木村
淳子 中久喜
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Chemical 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 Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp
Priority to JP61223913A priority Critical patent/JPH0737580B2/en
Publication of JPS6381165A publication Critical patent/JPS6381165A/en
Publication of JPH0737580B2 publication Critical patent/JPH0737580B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
    • G11B7/2495—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds as anions
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/2467—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes azo-dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)

Description

【発明の詳細な説明】 （ａ）発明の目的 （産業上の利用分野） 本発明は光吸収性を有するクロム含金アゾ系化合物、及
び同化合物を用いた光学記録媒体に関する。DETAILED DESCRIPTION OF THE INVENTION (a) Object of the Invention (Field of Industrial Application) The present invention relates to a chromium-containing azo compound having light absorption and an optical recording medium using the compound.

（従来の技術） レーザー光等を用いる光学記録は、情報を高密度に記録
保存でき、かつその記録を容易に再生利用できるもので
あり、その一例として光ディスクがあげられる。(Prior Art) Optical recording using a laser beam or the like allows information to be recorded and stored at a high density and the recording can be easily reproduced and used, and an example thereof is an optical disk.

一般に、光ディスクは、円形の基体に設けられた薄い記
録層に、１μｍ程度に集束したレーザー光を照射し、高
密度の情報記録を行なうものである。その記録は、照射
されたレーザー光エネルギーの吸収によって、その個所
の記録層に分解、蒸発、溶解等の熱的変形が生じること
により行なわれる。また、その記録された情報の再生
は、レーザー光により変形が起きている部分と起きてい
ない部分の反射率の差を読み取ることにより行なわれ
る。Generally, an optical disc is one in which a thin recording layer provided on a circular substrate is irradiated with a laser beam focused to about 1 μm to perform high density information recording. The recording is performed by the absorption of the irradiated laser light energy, which causes thermal deformation such as decomposition, evaporation, and dissolution in the recording layer at that location. The recorded information is reproduced by reading the difference in reflectance between the portion where the laser light is deformed and the portion where the deformation is not generated.

したがって、光学記録媒体の記録層は、レーザー光のエ
ネルギーを効率よく吸収する必要があるために、記録に
使用する特定の波長のレーザー光に対する吸収が大きい
こと、情報の再生に使用する特定の波長のレーザー光に
対する反射率が高いことが必要となる。Therefore, since the recording layer of the optical recording medium needs to efficiently absorb the energy of the laser light, it has a large absorption for the laser light of the specific wavelength used for recording, and the specific wavelength used for the reproduction of information. It is necessary that the laser light has a high reflectance.

この種の光学記録媒体としては、従来、種々の構成のも
のが知られている。たとえば、特開昭55−97033号公報
には、基板上にフタロシアニン系色素の単層を設けたも
のが開示されている。しかし、フタロシアニン系色素は
感度が低いし、分解点が高く蒸着しにくいし、さらに有
機溶媒に対する溶解性が著しく低いので、記録層を形成
せしめるための塗布によるコーティングが困難である等
の欠点がある。As this type of optical recording medium, various types of structures have been conventionally known. For example, JP-A-55-97033 discloses a substrate in which a single layer of a phthalocyanine dye is provided. However, since the phthalocyanine dye has low sensitivity, has a high decomposition point, is difficult to be vapor-deposited, and has extremely low solubility in an organic solvent, it has a drawback that coating by coating for forming a recording layer is difficult. .

また、特開昭58−83344号公報にはフエナレン系色素
を、特開昭58−224793号公報にはナフトキノン系色素を
記録層に設けたものが開示されている。しかし、これら
の色素は蒸着させやすい利点を有する反面において、反
射率が低いという欠点がある。反射率が低いと、レーザ
ー光による記録された部分と未記録部分との反射率のコ
ントラストが低くなり、記録された情報の再生が困難に
なる。Further, JP-A-58-83344 and JP-A-58-224793 disclose that a recording layer is provided with a phenalene dye and a naphthoquinone dye, respectively. However, while these dyes have the advantage of being easily vapor deposited, they have the drawback of low reflectance. If the reflectance is low, the contrast of the reflectance between the recorded portion and the unrecorded portion due to the laser light becomes low, and it becomes difficult to reproduce the recorded information.

また、特開昭59−24692号公報、特開昭59−67092号公
報、特開昭59−71895号公報には、シアニン系色素を記
録層に設けたものが開示されている。しかし、このよう
な色素は塗布によるコーティングが容易である利点があ
るが、耐光性に劣り、再生光による劣化を起す欠点があ
る。Further, JP-A-59-24692, JP-A-59-67092 and JP-A-59-71895 disclose a recording layer provided with a cyanine dye. However, although such a dye has an advantage that coating by coating is easy, it has a drawback that it has poor light resistance and deterioration due to reproducing light.

さらに、特公昭60−42269号公報には、含金アゾ系化合
物のアルカリ金属塩やアンモニウム塩等の色素を記録層
として設けたものが開示されている。しかし、その開示
された色素は有機溶媒に対する溶解性が不充分であり、
またその塗布膜は反射率が低く、しかもレーザー光の吸
収効率も低く、記録感度が著しく劣る。Further, Japanese Examined Patent Publication No. 60-42269 discloses a recording layer provided with a dye such as an alkali metal salt or ammonium salt of a metal-containing azo compound. However, the disclosed dyes have insufficient solubility in organic solvents,
Further, the coating film has a low reflectance and a low absorption efficiency of laser light, and thus the recording sensitivity is remarkably inferior.

（発明が解決しようとする問題点） 本発明は、有機溶媒に対する溶解性及び光反射率が高
く、耐光性及び再生光に対する耐性に優れた新規な色素
であるクロム含金アゾ系化合物の提供、及び同化合物を
光吸収色素として用いた光学記録媒体の提供を目的とす
るものである。(Problems to be Solved by the Invention) The present invention provides a chromium-containing azo compound which is a novel dye having high solubility in an organic solvent and high light reflectance, and excellent in light resistance and reproduction light resistance, Another object of the present invention is to provide an optical recording medium using the same compound as a light absorbing dye.

（ｂ）発明の構成 （問題点を解決するための手段） 本発明のクロム含金アゾ系化合物は、一般式 （式中、R1、R5はそれぞれニトロ基又はハロゲン原子を
表わし、R2、R3、R6、R7はそれぞれ水素原子、ニトロ基
又はハロゲン原子を表わし、R4、R8はそれぞれアミノ基
又はアミノ基の誘導体を表わし、Ｘ は四級ピリジニウ
ム誘導体を表わす。） で示される化合物である。(B) Structure of the Invention (Means for Solving Problems) The chromium-containing azo compound of the present invention has the general formula(In the formula, R1, RFiveAre nitro group or halogen atom,
Represent, R2, R3, R6, R7Are hydrogen atom and nitro group, respectively
Or represents a halogen atom, RFour, R8Are amino groups
Or represents a derivative of an amino group, X Is quaternary pyridiniu
It represents a murine derivative. ) Is a compound represented by.

また、本発明の光学記録媒体は、基板及び光吸収性色素
含有の記録層を有する光学記録媒体において、該光吸収
性色素が一般式 （式中、R1、R5はそれぞれニトロ基又はハロゲン原子を
表わし、R2、R3、R6、R7はそれぞれ水素原子、ニトロ基
又はハロゲン原子を表わし、R4、R8はそれぞれアミノ基
又はアミノ基の誘導体を表わし、Ｘ は四級ピリジニウ
ム誘導体を表わす。） で示されるクロム含金アゾ系化合物であることを特徴と
する記録媒体である。Further, the optical recording medium of the present invention comprises a substrate and a light absorbing dye.
In an optical recording medium having a recording layer containing
General formula(In the formula, R1, RFiveAre nitro group or halogen atom,
Represent, R2, R3, R6, R7Are hydrogen atom and nitro group, respectively
Or represents a halogen atom, RFour, R8Are amino groups
Or represents a derivative of an amino group, X Is quaternary pyridiniu
It represents a murine derivative. ) Is a chromium-containing azo compound represented by
Recording medium.

前記一般式（Ｉ）におけるR4、R8で示されるアミノ基の
誘導体の例としては、いずれも置換されていてもよいモ
ノアルキルアミノ基、ジアルキルアミノ基、アセチルア
ミノ基、ベンゾイルアミノ基等があげられ、その置換原
子又は置換基の例としては塩素原子、臭素原子、ヨウ素
原子等のハロゲン原子、ヒドロキシ基、シアノ基、アル
コキシ基等があげられる。Examples of the derivative of the amino group represented by R 4 and R 8 in the general formula (I) include a monoalkylamino group, a dialkylamino group, an acetylamino group, a benzoylamino group and the like, both of which may be substituted. Examples of the substituent atom or substituent include halogen atoms such as chlorine atom, bromine atom and iodine atom, hydroxy group, cyano group and alkoxy group.

また、前記一般式（Ｉ）におけるＸ で示される四級ピ
リジニウム誘導体としては、たとえば一般式 （式中、R9、R10はそれぞれ水素原子、それぞれ置換さ
れていてもよいアルキル基、ビニル基、アルコキシ基又
はハロゲン原子を表わし、R11は置換されていてもよい
アルキル基を表わす。） で示される誘導体があげられる。Further, X in the general formula (I) Fourth grade indicated by
Examples of the ridinium derivative include those represented by the general formula(In the formula, R9, RTenAre hydrogen atoms and
Optionally substituted alkyl group, vinyl group, alkoxy group or
Represents a halogen atom, R11May be replaced
Represents an alkyl group. ) The derivative shown by is mentioned.

前記一般式（II）におけるR9、R10で示されるアルキル
基やビニル基の置換基としては、たとえばアルコキシ
基、アルコキシアルコキシ基、アルコキシアルコキシア
ルコキシ基、アリルオキシ基、アリール基、アリールオ
キシ基、シアノ基、ヒドロキシ基、テトラヒドロフリル
基等があげられる。R9、R10として特に好ましいのは水
素原子、メチル基である。Examples of the substituent of the alkyl group or vinyl group represented by R 9 and R 10 in the general formula (II) include an alkoxy group, an alkoxyalkoxy group, an alkoxyalkoxyalkoxy group, an allyloxy group, an aryl group, an aryloxy group, and a cyano group. Group, hydroxy group, tetrahydrofuryl group and the like. Particularly preferred as R 9 and R 10 are a hydrogen atom and a methyl group.

前記一般式（II）におけるR11示されるアルキル基の置
換基としては、たとえばアルコキシ基、アルコキシアル
コキシ基、アルコキシアルコキシアルコキシ基、アリル
オキシ基、アリール基、アリールオキシ基、シアノ基、
ヒドロキシ基、テトラヒドロフリル基、ヒドロキシカル
ボニル基、アミノカルボニル基、ビニル基等があげられ
る。R11として特に好ましいものは炭素数８〜22の長鎖
アルキル基である。Examples of the substituent of the alkyl group represented by R 11 in the general formula (II) include an alkoxy group, an alkoxyalkoxy group, an alkoxyalkoxyalkoxy group, an allyloxy group, an aryl group, an aryloxy group, a cyano group,
Examples thereof include a hydroxy group, a tetrahydrofuryl group, a hydroxycarbonyl group, an aminocarbonyl group and a vinyl group. Particularly preferred as R 11 is a long-chain alkyl group having 8 to 22 carbon atoms.

本発明における前記一般式（Ｉ）で示される化合物とし
て好ましいものは、一般式（Ｉ）におけるＸ が前記一
般式（II）で表わされる四級ピリジニウム誘導体である
化合物である。As the compound represented by the above general formula (I) in the present invention,
And preferred is X in the general formula (I). Is the one
It is a quaternary pyridinium derivative represented by general formula (II).
It is a compound.

本発明の前記一般式（Ｉ）で示されるクロム含金アゾ化
合物は、600〜800nmの波長帯域で吸収を有し、しかも分
子吸収係数が104〜105cm-1である。The chromium-containing azo compound represented by the general formula (I) of the present invention has absorption in the wavelength band of 600 to 800 nm and has a molecular absorption coefficient of 10 4 to 10 5 cm -1 .

本発明における前記一般式（Ｉ）で示されるクロム含金
アゾ系化合物は、たとえば次の方法により製造すること
ができる。The chromium-containing azo compound represented by the general formula (I) in the present invention can be produced, for example, by the following method.

すなわち、まず、一般式 又は 〔各式中のR1、R2、R3、R5、R6、R7は前記一般式（Ｉ）
において定義したそれらと同じである。〕 で示されるヒドロキシアニリン誘導体を通常の方法でジ
アゾ化したものを、一般式 又は 〔各式中のR4、R8は前記一般式（Ｉ）において定義した
それらと同じである。〕 で示されるナフトール誘導体とカップリングさせて、一
般式 又は 〔各式中、R1、R2、R3、R4、R5、R6、R7、R8は前記一般
式（Ｉ）において定義したそれらと同じである。〕 で示されるジヒドロキシアゾ化合物を製造する。That is, first, the general formula Or [R 1 , R 2 , R 3 , R 5 , R 6 and R 7 in the formulas are each represented by the general formula (I).
Are the same as those defined in. ] The diazotized hydroxyaniline derivative represented by Or [R 4 and R 8 in each formula are the same as those defined in the above general formula (I). ] By coupling with a naphthol derivative represented by Or [In each formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are the same as those defined in the above general formula (I). ] The dihydroxy azo compound shown by these is manufactured.

次いで、前記一般式（Ｖ）又は（Ｖ′）で示される化合
物を酢酸クロムと反応させて金属錯化させてから、前記
一般式（II）で示される四級ピリジニウム誘導体と反応
させて塩を形成せしめれば、前記一般式（Ｉ）において
Ｘ が前記一般式（II）で示される四級ピリジニウム誘
導体である本発明のクロム含金アゾ系化合物が得られ
る。Then, a compound represented by the general formula (V) or (V ′)
After reacting the substance with chromium acetate to form a metal complex,
Reaction with quaternary pyridinium derivative represented by general formula (II)
To form a salt, in the general formula (I),
X Is a quaternary pyridinium derivative represented by the general formula (II).
A chromium-containing azo compound of the present invention, which is a conductor, is obtained.
It

この化合物（Ｉ）の上記の製造反応において、中間化合
物の（Ｖ）や（Ｖ′）として、前記のように１種類の化
合物（単一化合物）を用いた場合には、得られる化合物
（Ｉ）は、Crに対して対称構造の分子構造を有する化合
物となる。しかし、本発明の含金アゾ系化合物は、かか
る対称構造の分子構造を有するものに限らない。前記の
製造反応において、中間化合物の（Ｖ）又は（Ｖ′）の
代りに、いずれもかかる化合物に属するが、実質上２種
類（又はそれ以上）の化合物の混合物を用いて反応を行
なわせた場合には、いずれも前記一般式（Ｉ）で示され
る化合物に該当するが、しかし対称構造を有する化合物
と非対称構造を有する化合物との数種の化合物の混合物
が得られる。かかる数種の化合物の混合物は、適当な分
離手段（たとえばシリカゲルカラムクロマトグラフィ
ー）を用いれば、いずれも一般式（Ｉ）に該当する数種
の単一化合物に分離することができ、かくして分離され
た各化合物は、対称構造のものであっても、或いは非対
称構造のものであっても、いずれも本発明の化合物に該
当するのは勿論であるし、いずれも本発明の光学記録媒
体用の光吸収性色素として有効に使用することができ
る。When one kind of compound (single compound) is used as the intermediate compound (V) or (V ') in the above production reaction of the compound (I), the resulting compound (I ) Is a compound having a molecular structure symmetrical to Cr. However, the metal-containing azo compound of the present invention is not limited to those having such a symmetrical molecular structure. In the above-mentioned production reaction, instead of the intermediate compound (V) or (V '), the reaction was carried out using a mixture of substantially two (or more) compounds which belong to such compounds. In this case, all correspond to the compound represented by the general formula (I), but a mixture of several kinds of compounds having a symmetrical structure and a compound having an asymmetric structure is obtained. Such a mixture of several compounds can be separated into several single compounds corresponding to the general formula (I) by using an appropriate separation means (for example, silica gel column chromatography), and thus separated. It goes without saying that each of the compounds, whether having a symmetric structure or an asymmetric structure, corresponds to the compound of the present invention, and all of them are for the optical recording medium of the present invention. It can be effectively used as a light absorbing dye.

次に、本発明の光学記録媒体は、基本的には基板と前記
一般式（Ｉ）で示されるクロム含金アゾ系化合物を含有
する記録層とから構成されるが、さらに必要に応じて基
板上に下引き層を、また記録層上に保護層を設けること
ができる。Next, the optical recording medium of the present invention basically comprises a substrate and a recording layer containing the chromium-containing azo compound represented by the general formula (I). An undercoat layer may be provided on the upper side, and a protective layer may be provided on the recording layer.

本発明における基板としては、使用するレーザー光に対
して透明又は不透明のいずれであってもよい。基板の材
質としては、ガラス、プラスチック、紙、板状若しくは
箔状の金属等の一般のこの種記録体用の支持体が使用で
きるが、種々の点からしてプラスチックが好ましい。そ
のプラスチックとしては、たとえばアクリル樹脂、メタ
クリル樹脂、酢酸ビニル樹脂、塩化ビニル樹脂、ニトロ
セルロース、ポリエチレン樹脂、ポリプロピレン樹脂、
ポリカーボネート樹脂、ポリイミド樹脂、ポリサルホン
樹脂、エポキシ樹脂等があげられる。The substrate in the present invention may be transparent or opaque to the laser light used. As the material of the substrate, a general support for this type of recording medium such as glass, plastic, paper, plate-shaped or foil-shaped metal can be used, but plastic is preferable from various points. Examples of the plastic include acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin,
Examples thereof include polycarbonate resin, polyimide resin, polysulfone resin, and epoxy resin.

本発明の光学記録媒体におけるクロム含金アゾ系化合物
を含有する記録層の厚さは、100Å〜５μｍ、好ましく
は500Å〜３μｍである。The thickness of the recording layer containing the chromium-containing azo compound in the optical recording medium of the present invention is 100Å to 5 μm, preferably 500Å to 3 μm.

その記録層形成のための成膜法としては、真空蒸着法、
スパッタリング法、ドクターブレード法、キヤスト法、
スピナー法、浸漬法などの一般的に行なわれている薄膜
形成法が用いられる。As a film forming method for forming the recording layer, a vacuum vapor deposition method,
Sputtering method, doctor blade method, cast method,
A commonly used thin film forming method such as a spinner method or a dipping method is used.

その記録層の形成には、クロム含金アゾ系化合物にバイ
ンダーを併用することができ、そのバインダーとしては
ポリビニルアルコール、ポリビニルピロリドン、ニトロ
セルロース、酢酸セルロース、ポリビニルブチラール、
ポリカーボネートなどの樹脂類が使用される。これらの
樹脂類の使用量は、クロム含金アゾ系化合物が樹脂類に
対して重量比で0.1以上になる割合が望ましい。To form the recording layer, a binder can be used in combination with the chromium-containing azo compound, and as the binder, polyvinyl alcohol, polyvinylpyrrolidone, nitrocellulose, cellulose acetate, polyvinyl butyral,
Resins such as polycarbonate are used. The amount of these resins used is preferably such that the chromium-containing azo compound is 0.1 or more in weight ratio with respect to the resins.

前記のドクターブレード法、キヤスト法、スピナー法、
浸漬法、特にスピナー法で記録層を形成する場合には塗
布溶媒が使用され、その溶媒としては、たとえばテトラ
クロロエタン、ブロモホルム、ジブロモエタン、エチル
セロソルブ、キシレン、クロロベンゼン、シクロヘキサ
ノン等の沸点が120〜160℃の溶媒が好適に使用される。
また、スピナー法による成膜は回転数500〜5000rpmが好
ましく、スピンコート後に、場合によって加熱或いは溶
媒蒸気にあてるなどの処理を行なってもよい。Doctor blade method, cast method, spinner method,
A coating solvent is used when the recording layer is formed by the dipping method, especially the spinner method, and examples of the solvent include tetrachloroethane, bromoform, dibromoethane, ethyl cellosolve, xylene, chlorobenzene, and cyclohexanone having a boiling point of 120 to 160. Solvents at ° C are preferably used.
In addition, the film formation by the spinner method is preferably at a rotation speed of 500 to 5000 rpm, and after spin coating, treatment such as heating or applying to solvent vapor may be performed depending on the case.

記録層には、記録層の安定性や耐光性向上のために、一
重項酸素クエンチヤーとして遷移金属キレート化合物
（たとえばアセチルアセトナートキレート、ビスフェニ
ルジチオール、サリチルアルデヒドオキシム、ビスジチ
オール−α−ジケトン等）又は三級アミン化合物を含有
せしめてもよい。In order to improve the stability and light resistance of the recording layer, a transition metal chelate compound (eg, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithiol-α-diketone, etc.) is used as a singlet oxygen quencher in the recording layer. Alternatively, a tertiary amine compound may be contained.

さらに、記録層には必要に応じて他の色素を併用するこ
とができる。その他の色素としてはナフトラクタム系色
素、トリアリールメタン系色素、アゾ色素、シアニン系
色素、スクアリリウム系色素、インドアニリン系色素、
メチン系色素、ナフタロシアニン系色素、フタロシアニ
ン系色素、含金アゾ系色素などがあげられる。Furthermore, other dyes can be used in combination in the recording layer, if desired. Other dyes include naphtholactam dyes, triarylmethane dyes, azo dyes, cyanine dyes, squarylium dyes, indoaniline dyes,
Examples thereof include methine dyes, naphthalocyanine dyes, phthalocyanine dyes, and metal-containing azo dyes.

本発明の光学記録媒体における記録層は基板の両面に設
けてもよいし、片面だけに設けてもよい。The recording layer in the optical recording medium of the present invention may be provided on both sides of the substrate, or may be provided on only one side.

本発明の光学記録媒体への記録は、基板の両面又は片面
に設けられた記録層に１μｍ程度に集束したレーザー
光、好ましくは半導体レーザー光をあてることにより行
なう。レーザー光の照射された部分には、レーザー光エ
ネルギーの吸収による分解、蒸発、溶融等の記録層の熱
的変形が起こり、情報が記録される。Recording on the optical recording medium of the present invention is performed by irradiating a recording layer provided on both sides or one side of the substrate with a laser beam focused to about 1 μm, preferably a semiconductor laser beam. In the portion irradiated with the laser light, thermal deformation of the recording layer such as decomposition, evaporation and melting due to absorption of laser light energy occurs, and information is recorded.

その記録された情報の再生は、レーザー光により、熱的
変形が起きていない部分と起きている部分の反射率の差
を読み取ることにより行なう。Reproduction of the recorded information is performed by reading the difference in reflectance between a portion where thermal deformation has not occurred and a portion where thermal deformation has occurred, with a laser beam.

本発明の光学記録媒体の記録及び再生に使用されるレー
ザーとしては、N2,He−Cd,Ar,He−Ne,ルビー、半導体、
色素レーザーなどがあげられるが、特に軽量性、取扱い
の容易さ、コンパクト性などの点からして半導体レーザ
ーが好ましい。As a laser used for recording and reproducing of the optical recording medium of the present invention, N 2, He-Cd, Ar, He-Ne, ruby, semiconductor,
Examples thereof include dye lasers, and semiconductor lasers are preferable from the viewpoints of lightness, easy handling, compactness, and the like.

（実施例等） 以下に実施例及び比較例をあげてさらに詳述する。(Examples, etc.) Hereinafter, examples and comparative examples will be described in more detail.

実施例１ クロム含金アゾ化合物の合成： 水420ml及び構造式 で表わされる化合物23.1g（0.15モル）を０〜５℃に冷
却し、濃塩酸33.2mlを加え、さらに亜硝酸ナトリウム1
0.9g及び水45mlの溶液を滴下し、０〜５℃で３時間ジア
ゾ化し、さらにスルファミン酸0.3gを加え、ジアゾ液と
した。Example 1 Synthesis of chromium-containing azo compound: 420 ml of water and structural formula 23.1 g (0.15 mol) of the compound represented by is cooled to 0 to 5 ° C, 33.2 ml of concentrated hydrochloric acid is added, and further sodium nitrite 1
A solution of 0.9 g and 45 ml of water was added dropwise, diazotization was carried out at 0 to 5 ° C for 3 hours, and 0.3 g of sulfamic acid was further added to obtain a diazo solution.

また、構造式 で表わされる化合物23.9g（0.15モル）をエタノール300
mlに加え、０〜５℃に冷却し、これに前記のジアゾ液を
適下しながら、20％NaOH水溶液でpHを７〜９にコントロ
ールしてカップリング反応させ、１夜放置後、過し、
さらにメタノールに懸濁してから過、乾燥して、下記
の構造式で表わされるモノアゾ化合物40gを得た。Also, the structural formula 23.9 g (0.15 mol) of the compound represented by
Add to the mixture, cool to 0-5 ° C, adjust the pH to 7-9 with 20% NaOH aqueous solution while applying the above diazo solution, and allow it to react for coupling overnight. ,
Further, the product was suspended in methanol, filtered, and dried to obtain 40 g of a monoazo compound represented by the following structural formula.

このモノアゾ化合物6.48g（0.02モル）、酢酸クロム5.4
g、N,N−ジメチルホルムアミド30mlの混合物を、還流下
で５時間反応させた。得られた反応液に、構造式 で表わされる四級ピリジニウム化合物5.3gを氷水500ml
に溶解し、さらにギ酸で酸性にした溶液を加え、室温で
１時間撹拌した。生成した沈でん物の黒色結晶を別
し、乾燥して下記の構造式で表わされる本発明のクロム
含金アゾ化合物（黒色結晶）14gを得た。 This monoazo compound 6.48 g (0.02 mol), chromium acetate 5.4
A mixture of g, N, N-dimethylformamide (30 ml) was reacted under reflux for 5 hours. The obtained reaction solution has a structural formula 5.3 g of a quaternary pyridinium compound represented by
Was added, and a solution acidified with formic acid was added, followed by stirring at room temperature for 1 hour. Black crystals of the produced precipitate were separated and dried to obtain 14 g of a chromium-containing azo compound (black crystal) of the present invention represented by the following structural formula.

この化合物の特性値は下記のとおりであった。 The characteristic values of this compound are as follows.

λmax（クロロホルム溶液） 665nm 融点 223〜225℃（dec） 光学記録媒体： 前記構造式のクロム含金アゾ化合物1.5gをシクロヘキサ
ノン50gに溶解し、0.22μｍのフィルターで過して溶
液を得た。λmax (chloroform solution) 665 nm melting point 223 to 225 ° C. (dec) Optical recording medium: 1.5 g of the chromium-containing azo compound of the above structural formula was dissolved in 50 g of cyclohexanone, and the solution was passed through a 0.22 μm filter to obtain a solution.

この溶液2mlを、深さ700Å、巾0.7μｍの紫外線硬化樹
脂による溝（グループ）を有するメタクリル樹脂（以
下、「PMMA」という。）の基板（120mmφ）上に滴下
し、スピナー法により1000rpmの回転数で塗布したの
ち、60℃で10分間乾燥した。塗布膜の最大吸収波長は68
0nmであり、そのスペクトルの形状は巾広かった。ま
た、その塗布膜の吸光度と反射率曲線は添付図面に示す
とおりであり、反射率のピークは830nmであり、830nmに
おける反射率は30％であった。2 ml of this solution was dropped on a methacrylic resin (hereinafter referred to as "PMMA") substrate (120 mmφ) having a groove (group) made of an ultraviolet curable resin with a depth of 700 Å and a width of 0.7 μm, and spun at 1000 rpm by a spinner method. After coating with a number, it was dried at 60 ° C. for 10 minutes. The maximum absorption wavelength of the coating film is 68
It was 0 nm, and the shape of the spectrum was broad. Further, the absorbance and reflectance curve of the coating film are as shown in the attached drawings, the reflectance peak was 830 nm, and the reflectance at 830 nm was 30%.

この塗布膜（記録層）に、中心波長830nmの半導体レー
ザー光（出力6mW、ビーム１μｍ）を照射したところ、
巾約１μｍ、ピット長約２μｍの輪郭の極めて明瞭な孔
（ピット）が形成された。そのキャリヤーレベル／ノイ
ズレベル（C/N）比比は高く、耐光性及び再生光に対す
る耐性も良好であった。When this coating film (recording layer) was irradiated with a semiconductor laser beam having a central wavelength of 830 nm (output 6 mW, beam 1 μm),
An extremely clear hole (pit) having a width of about 1 μm and a pit length of about 2 μm was formed. The carrier level / noise level (C / N) ratio was high, and the light resistance and reproduction light resistance were also good.

実施例２ 実施例１の合成法に準じて、下記の構造式で示される本
発明のクロム含金アゾ化合物を製造したところ、そのλ
max（クロロホルム溶液）は668nm、融点は178℃（溶融
しはじめ）であった。Example 2 According to the synthesis method of Example 1, a chromium-containing azo compound of the present invention represented by the following structural formula was produced.
The maximum (chloroform solution) was 668 nm, and the melting point was 178 ° C (beginning to melt).

このクロム含金アゾ化合物1g及びニトロセルロース（ダ
イセル化学工業株式会社商品名RS−20）1.5gをメチルエ
チルケトン50gに溶解し、0.22μｍのフィルターで過
して溶液を得た。この溶液3mlを深さ650Å、巾0.7μｍ
の紫外線硬化樹脂による溝（グループ）を有するPMMA樹
脂基板（120mmφ）上に滴下し、1500rpmの回転数で塗布
したのち、60℃で10分間乾燥した。得られた塗夫膜の最
大吸収波長は690nmであり、反射率のピークは840nmであ
った。 1 g of this chromium-containing azo compound and 1.5 g of nitrocellulose (trade name RS-20, manufactured by Daicel Chemical Industries, Ltd.) were dissolved in 50 g of methyl ethyl ketone and filtered through a 0.22 μm filter to obtain a solution. 3 ml of this solution is 650 Å in depth and 0.7 μm in width
Was dripped onto a PMMA resin substrate (120 mmφ) having grooves (groups) made of the UV curable resin, and applied at a rotation speed of 1500 rpm, and then dried at 60 ° C. for 10 minutes. The coating film thus obtained had a maximum absorption wavelength of 690 nm and a reflectance peak of 840 nm.

この塗布膜（記録層）に、中心波長830nmの半導体レー
ザー光（出力6mW、ビーム径１μｍ）で照射したとこ
ろ、巾約１μｍ、ピット長約２μｍの輪郭の極めて明瞭
な孔（ピット）が形成された。そのC/N比が高く、耐光
性及び再生光に対する耐性も良好であった。When this coating film (recording layer) was irradiated with a semiconductor laser beam having a central wavelength of 830 nm (output 6 mW, beam diameter 1 μm), extremely clear holes (pits) with a width of about 1 μm and a pit length of about 2 μm were formed. It was Its C / N ratio was high, and its light resistance and reproduction light resistance were also good.

実施例３ 実施例１の合成法に準じて、下記の構造式で示される本
発明のクロム含金アゾ化合物を製造したところ、そのλ
max（クロロホルム溶液）は670nm、融点は176℃（溶融
しはじめ）〜220℃（分解）であった。Example 3 According to the synthesis method of Example 1, a chromium-containing azo compound of the present invention represented by the following structural formula was produced.
The max (chloroform solution) was 670 nm, and the melting point was 176 ° C (beginning to melt) to 220 ° C (decomposition).

このクロム含金アゾ化合物1.5gをシクロヘキサン50gに
溶解し、0.22μｍのフィルターで過し溶液を得た。こ
の溶液2mlを深さ700Å、巾0.7μｍの紫外線硬化樹脂に
よる溝（グループ）を有するPMMA樹脂基板（130mmφ）
上に滴下し、800rpmの回転数で塗布したのち、60℃で20
分間乾燥した。塗布膜の最大吸収波長は690nmであり、
反射率のピークは830nmであり、スペクトル曲線は巾広
かった。 1.5 g of this chromium-containing azo compound was dissolved in 50 g of cyclohexane and passed through a 0.22 μm filter to obtain a solution. PMMA resin substrate (130 mmφ) with 2 ml of this solution having a depth (700 Å) and a groove (group) of 0.7 μm width made of UV curable resin
Drop it on top and apply it at a rotation speed of 800 rpm, and then at 20 ° C at 20 ° C.
Dry for minutes. The maximum absorption wavelength of the coating film is 690 nm,
The reflectance peak was 830 nm, and the spectrum curve was broad.

この塗布膜（記録層）に、中心波長830nmの半導体レー
ザー光（出力6mW、ビーム径１μｍ）で照射したとこ
ろ、巾約１μｍ、ピット長約２μｍの輪郭の極めて明瞭
な孔（ピット）が形成された。そのC/N比は高く、耐光
性及び再生光に対する耐性も良好であった。When this coating film (recording layer) was irradiated with a semiconductor laser beam having a central wavelength of 830 nm (output 6 mW, beam diameter 1 μm), extremely clear holes (pits) with a width of about 1 μm and a pit length of about 2 μm were formed. It was Its C / N ratio was high, and its light resistance and reproduction light resistance were also good.

比較例１〜３ 実施例１の合成法に準じて、下記の各構造式で示される
クロム含金アゾ化合物をそれぞれ合成した。Comparative Examples 1 to 3 According to the synthesis method of Example 1, chromium-containing azo compounds represented by the following structural formulas were respectively synthesized.

得られた各クロム含金アゾ化合物の有機溶媒に対する溶
解性、塗布膜（３％シクロヘキサノン溶液を用いて形成
された塗布膜）の吸光度（690nmにおける）及び反射率
（830nmにおける）、並びに塗布膜の記録感度（830nmの
半導体レーザー光、出力6mW、ビーム１μｍ）は、第１
表にそれぞれ示すとおりであった。なお、第１表には実
施例１〜３のクロム含金アゾ化合物の同様のデータも併
記した。 Solubility of each obtained chromium-containing azo compound in an organic solvent, absorbance (at 690 nm) and reflectance (at 830 nm) of a coating film (coating film formed using a 3% cyclohexanone solution), and coating film Recording sensitivity (830 nm semiconductor laser light, output 6 mW, beam 1 μm)
The results are shown in the table. In addition, Table 1 also shows similar data of the chromium-containing azo compounds of Examples 1 to 3.

実施例４〜32 実施例１の合成法に準ずる方法で、下記の第２表に記載
の化学構造式を有する種々のクロム含金アゾ系化合物を
製造した。得られた各化合物のクロロホルム溶媒中の最
大吸収波長は第２表に示すとおりであった。 Examples 4 to 32 Various chromium-containing azo compounds having the chemical structural formulas shown in Table 2 below were produced by a method similar to the synthesis method of Example 1. The maximum absorption wavelength of each compound obtained in chloroform was as shown in Table 2.

また、その各化合物を用い、実施例１におけると同様の
条件で紫外線硬化樹脂による溝（グルーブ）を有するPM
MA樹脂基板上に塗布した。得られた塗布膜（記録層）の
最大吸収波長は第２表に示すとおりであった。また、こ
の各塗布膜に、中心波長830nmの半導体レーザー光を照
射したところ、輪郭の極めて明瞭な孔（ピット）が形成
され、反射率が高く、高感度でC/N比が優れていた。ま
た、耐光性及び再生光に対する耐性も良好であった。Further, using each of the compounds, PM having a groove made of an ultraviolet curable resin under the same conditions as in Example 1
It was applied on an MA resin substrate. The maximum absorption wavelength of the obtained coating film (recording layer) was as shown in Table 2. When each coating film was irradiated with a semiconductor laser beam having a central wavelength of 830 nm, holes (pits) with extremely clear contours were formed, high reflectance, high sensitivity, and excellent C / N ratio. Further, the light resistance and the resistance to reproduction light were also good.

実施例33 構造式 で表わされるモノアゾ化合物9.25g（0.02モル）、及び
構造式 で表わされるモノアゾ化合物8.5g（0.02モル）に酢酸ク
ロム5.4g、N,N−ジメチルホルムアミド50mlを加えた混
合物を、還流下で７時間反応させた。 Example 33 Structural formula 9.25 g (0.02 mol) of monoazo compound represented by, and structural formula A mixture obtained by adding 5.4 g of chromium acetate and 50 ml of N, N-dimethylformamide to 8.5 g (0.02 mol) of the monoazo compound represented by the above was reacted under reflux for 7 hours.

得られた反応液に、構造式 で示される四級ピリジニウム化合物5.5gを氷水500mlに
溶解し、さらにギ酸で酸性にした溶液を加え、室温で１
時間撹拌した。The obtained reaction solution has a structural formula 5.5 g of the quaternary pyridinium compound represented by is dissolved in 500 ml of ice water, and a solution acidified with formic acid is added to
Stir for hours.

生成沈でん物の黒色結晶を別し、乾燥して、クロム含
金アゾ化合物の混合物を得た。この混合物をシリカゲル
カラムクロマトグラフィー（溶媒:n−ブタノール／エタ
ノール／酢酸／水＝9/1/1/1）によって分離精製し、下
記の構造式及び最大吸収波長を有する３種類のクロム含
金アゾ化合物（いずれも黒色結晶）を、それぞれ記載の
収量で得た。Black crystals of the formed precipitate were separated and dried to obtain a mixture of chromium-containing azo compound. This mixture was separated and purified by silica gel column chromatography (solvent: n-butanol / ethanol / acetic acid / water = 9/1/1/1), and three types of chromium-containing azo having the following structural formulas and maximum absorption wavelengths were used. The compounds (all black crystals) were obtained in the yields indicated.

λmax（クロロホルム溶液）680nm 収量3.0g 非対象構造 λmax（クロロホルム溶液）680nm 収量3.2g 対称構造 λmax（クロロホルム溶液）680nm 収量3.0g 対称構造 実施例34〜35 実施例33の合成法に準ずる方法を用いて、下記の構造式
及び最大吸収波長を有する２種類のいずれも非対称構造
のクロム含金アゾ化合物を得た。 λmax (chloroform solution) 680nm Yield 3.0g Non-target structure λmax (chloroform solution) 680nm Yield 3.2g Symmetrical structure λmax (chloroform solution) 680 nm Yield 3.0 g Symmetrical structure Examples 34 to 35 Using a method similar to the synthesis method of Example 33, the following structural formula and two types of asymmetrical chromium-containing metal having the maximum absorption wavelength were used. An azo compound was obtained.

λmax（クロロホルム溶液）700nm λmax（塗布膜）710nm λmax（クロロホルム溶液）710nm λmax（塗布膜）730nm （ｃ）発明の効果 本発明のクロム含金アゾ化合物は、有機溶剤に対する溶
解性及び反射率が高く、かつ耐光性に優れている。した
がって、同化合物を記録層に含有せしめた本発明の光学
記録媒体は、その記録層を塗布によるコーティングで形
成せしめることができ、その記録層はコントラストが良
好で、耐光性及び再生光による耐性に優れている。 λmax (chloroform solution) 700nm λmax (coating film) 710nm λmax (chloroform solution) 710 nm λmax (coating film) 730 nm (c) Effect of the invention The chromium-containing azo compound of the present invention has high solubility and reflectance in an organic solvent and excellent light resistance. Therefore, the optical recording medium of the present invention in which the same compound is contained in the recording layer can be formed by coating the recording layer, and the recording layer has good contrast, light resistance and resistance to reproducing light. Are better.

【図面の簡単な説明】[Brief description of drawings]

添付図面は、実施例１の記録層の吸光度と反射率曲線を
図示したものである。The accompanying drawings show the absorbance and reflectance curves of the recording layer of Example 1.

Claims (4)

【特許請求の範囲】[Claims] 【請求項１】一般式 （式中、R1、R5はそれぞれニトロ基又はハロゲン原子を
表わし、R2、R3、R6、R7はそれぞれ水素原子、ニトロ基
又はハロゲン原子を表わし、R4、R8はそれぞれアミノ基
又はアミノ基の誘導体を表わし、Ｘ は四級ピリジニウ
ム誘導体を表わす。） で示されるクロム含金アゾ系化合物。1. A general formula(In the formula, R1, RFiveAre nitro group or halogen atom,
Represent, R2, R3, R6, R7Are hydrogen atom and nitro group, respectively
Or represents a halogen atom, RFour, R8Are amino groups
Or represents a derivative of an amino group, X Is quaternary pyridiniu
It represents a murine derivative. ) A chromium-containing azo compound represented by: 【請求項２】一般式におけるＸ が、一般式 （式中、R9、R10はそれぞれ水素原子、それぞれ置換さ
れていてもよいアルキル基、ビニル基、アルコキシ基又
はハロゲン原子を表わし、R11は置換されていてもよい
アルキル基を表わす。） で示される四級ピリジニウム誘導体である特許請求の範
囲第１項記載の化合物。2. X in the general formula But the general formula(In the formula, R9, RTenAre hydrogen atoms and
Optionally substituted alkyl group, vinyl group, alkoxy group or
Represents a halogen atom, R11May be replaced
Represents an alkyl group. ) A quaternary pyridinium derivative represented by
A compound according to item 1. 【請求項３】基板及び光吸収性色素含有の記録層を有す
る光学記録媒体において、該光吸収性色素が一般式 （式中、R1、R5はそれぞれニトロ基又はハロゲン原子を
表わし、R2、R3、R6、R7はそれぞれ水素原子、ニトロ基
又はハロゲン原子を表わし、R4、R8はそれぞれアミノ基
又はアミノ基の誘導体を表わし、Ｘ は四級ピリジニウ
ム誘導体を表わす。） で示されるクロム含金アゾ系化合物であることを特徴と
する光学記録媒体。3. A substrate and a recording layer containing a light absorbing dye.
In the optical recording medium, the light absorbing dye has the general formula(In the formula, R1, RFiveAre nitro group or halogen atom,
Represent, R2, R3, R6, R7Are hydrogen atom and nitro group, respectively
Or represents a halogen atom, RFour, R8Are amino groups
Or represents a derivative of an amino group, X Is quaternary pyridiniu
It represents a murine derivative. ) Is a chromium-containing azo compound represented by
Optical recording medium. 【請求項４】一般式におけるＸ が、一般式 （式中、R9、R10はそれぞれ水素原子、それぞれ置換さ
れていてもよいアルキル基、ビニル基、アルコキシ基又
はハロゲン原子を表わし、R11は置換されていてもよい
アルキル基を表わす。） で示される四級ピリジニウム誘導体である特許請求の範
囲第３項記載の光学記録媒体。4. X in the general formula But the general formula(In the formula, R9, RTenAre hydrogen atoms and
Optionally substituted alkyl group, vinyl group, alkoxy group or
Represents a halogen atom, R11May be replaced
Represents an alkyl group. ) A quaternary pyridinium derivative represented by
The optical recording medium according to item 3.
JP61223913A 1986-09-24 1986-09-24 Chromium-containing azo compound and optical recording medium containing the same Expired - Lifetime JPH0737580B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP61223913A JPH0737580B2 (en) 1986-09-24 1986-09-24 Chromium-containing azo compound and optical recording medium containing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP61223913A JPH0737580B2 (en) 1986-09-24 1986-09-24 Chromium-containing azo compound and optical recording medium containing the same

Publications (2)

Publication Number Publication Date
JPS6381165A JPS6381165A (en) 1988-04-12
JPH0737580B2 true JPH0737580B2 (en) 1995-04-26

Family

ID=16805672

Family Applications (1)

Application Number Title Priority Date Filing Date
JP61223913A Expired - Lifetime JPH0737580B2 (en) 1986-09-24 1986-09-24 Chromium-containing azo compound and optical recording medium containing the same

Country Status (1)

Country Link
JP (1) JPH0737580B2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5272047A (en) * 1992-06-26 1993-12-21 Eastman Kodak Company Optical information recording medium using azo dyes
EP0887202B1 (en) 1996-12-27 2004-05-06 TDK Corporation Optical recording medium
JP4743994B2 (en) * 2000-10-27 2011-08-10 株式会社林原生物化学研究所 Light resistance improver
JP2003063139A (en) * 2001-08-27 2003-03-05 Ricoh Co Ltd Optical recording medium

Also Published As

Publication number Publication date
JPS6381165A (en) 1988-04-12

Similar Documents

Publication Publication Date Title
JPH11334205A (en) Optical recording medium
JPH11334204A (en) Optical recording medium
JP4178783B2 (en) Optical recording medium
JP2870952B2 (en) Optical recording medium
US5447823A (en) Metal chelate compound and optical recording medium using the compound
JPH0737580B2 (en) Chromium-containing azo compound and optical recording medium containing the same
JP3175279B2 (en) Metal chelate compound and optical recording medium using the compound
JP2685054B2 (en) Naphthoquinone methide compounds
JP3876970B2 (en) Dye for recording layer formation of optical recording medium, optical recording medium using the same, and recording method of optical recording medium
JPH0776308B2 (en) Indophenol compound and optical recording medium containing the compound
JP3772047B2 (en) Optical recording medium
JP2731930B2 (en) Methine compound and optical recording medium containing the compound
JP2600763B2 (en) Metal-containing compound and optical recording medium using the compound
JP2727463B2 (en) Naphthoquinone diimine compound and optical recording medium containing the compound
JP3972571B2 (en) Metal chelate dye and optical recording medium containing the same
JPH0816199B2 (en) Naphthoquinone methide compounds
JP2727464B2 (en) Metal-containing indophenol compound and optical recording medium using the compound
JPH0713193B2 (en) Dioxadinaphthopentacene derivative and optical recording medium using the derivative
JP2002002117A (en) Optical recording medium
JP2890407B2 (en) Optical recording medium
JPH0280466A (en) Azulene compound
JPH0276884A (en) Metal-contailing pyridophenothiazone compound
JPH0665514A (en) Metal chelate compound and optical recording medium obtained using the same
JPS63276593A (en) Optical recording medium
JPH07103124B2 (en) Dioxapentacene derivative and optical recording medium using the derivative