JPH01165565A - Azamethine compound, production thereof and optical information recording medium using said compound - Google Patents

Azamethine compound, production thereof and optical information recording medium using said compound

Info

Publication number
JPH01165565A
JPH01165565A JP62325998A JP32599887A JPH01165565A JP H01165565 A JPH01165565 A JP H01165565A JP 62325998 A JP62325998 A JP 62325998A JP 32599887 A JP32599887 A JP 32599887A JP H01165565 A JPH01165565 A JP H01165565A
Authority
JP
Japan
Prior art keywords
tables
formulas
optionally substituted
chemical formulas
group
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
Application number
JP62325998A
Other languages
Japanese (ja)
Inventor
Takeshi Hioki
毅 日置
Atsushi Tomioka
淳 富岡
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.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
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 Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP62325998A priority Critical patent/JPH01165565A/en
Priority to US07/179,251 priority patent/US5028708A/en
Priority to DE88303379T priority patent/DE3883583T2/en
Priority to EP88303379A priority patent/EP0287377B1/en
Publication of JPH01165565A publication Critical patent/JPH01165565A/en
Priority to US07/383,081 priority patent/US5061796A/en
Priority to US07/684,290 priority patent/US5136054A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/66—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

NEW MATERIAL:A compound shown by formula I [X is group shown by formula II-IV IV; R1-R4 are H, alkyl, alkoxy or amino which may contain substituent group, halogen, NO2, CN, OH, etc.; R5 and R6 are H, alkyl or aryl which may contain substituent group, cyclohexyl or R5 and R6 form ring which may contain hetero atom: R7 alkoxy which may contain substituent group, OH, halogen, CN or OCOR''; R'' is alkyl which may contain substituent group; R8 is H, alkyl or alkoxy which may contain substituent group or halogen; R9-R11 are H or alkyl]. EXAMPLE:A compound shown by formula V. USE:An optical information recording medium having large absorption and reflection on laser beam of semiconductor and stability to light and heat. Further fine color decomposition filter useful for image pack-up element or color display. PREPARATION:A compound shown by formula VI is reacted with a compound shown by the formula X-N=0 to give a compound shown by formula I.

Description

【発明の詳細な説明】 〈産業上の利用分野〉 本発明は、アザメチン系化合物、その製法及びそれを用
いた光情報記録媒体に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to an azamethine compound, a method for producing the same, and an optical information recording medium using the same.

〈従来の技術〉 本系統化合物の用途としては、光情報記録媒体用、カラ
ー撮像素子及びカラーデイスプレー用の微細色分解フィ
ルター用などがある。<Prior Art> Applications of this series of compounds include optical information recording media, fine color separation filters for color image sensors and color displays, and the like.

上記分野、特に光記録媒体は媒体と書き込みないし読み
出し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、このため、種々の光５己録媒体
の開発研究が行われている。In the above fields, especially optical recording media, since there is no contact between the medium and the writing or reading head, the recording medium does not deteriorate due to wear and tear.For this reason, research and development of various optical recording media are being carried out. .

このような光記録媒体のうち、暗室による現像処理が不
要である等の点で、ヒートモード光記録媒体の開発が活
発になっている。このヒートモードの光記録媒体は、記
録光を熱として利用する光。Among such optical recording media, heat mode optical recording media are being actively developed because they do not require development in a dark room. This heat mode optical recording medium uses recording light as heat.

記録媒体であり、その−例として、レーザー等の記録光
で媒体の一部を融解、除去等して、ピットと称される小
穴を形成して書き込みを行い、このピットにより情報を
記録し、このピットを読み出し光で検出して読み出しを
行うピット形成タイプのものがある。A recording medium, for example, a part of the medium is melted or removed using a recording beam such as a laser to form small holes called pits, and information is recorded through these pits. There is a pit-forming type that detects these pits with readout light and performs readout.

したがって、光記録媒体は、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、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
再生を正確に行うため、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, optical recording media must absorb the energy of laser light efficiently, so they must have a high absorption of laser light of a specific wavelength used for recording, and in order to reproduce information accurately, It is necessary to have a high reflectance for laser light of a specific wavelength.

このようなビット形成タイプの記録媒体、特にそのうち
、装置を小型化できる半導体レーザーを光源とするもの
においてはこれまで、Ｔｅを主体とする材料を記録層と
するものが大半をしめている。Most of such bit-forming type recording media, particularly those using a semiconductor laser as a light source that can miniaturize the device, have a recording layer made of a material mainly composed of Te.

しかし、近年、Ｔｅ系材料が環境汚染の問題があること
、そしてより高感度化する必要があること、より製造コ
ストを安価にする必要があること等から、Ｔｅ系にかえ
有機色素を主とした有機系材料の記録層を用いる記録媒
体についての提案や報告が増加している。However, in recent years, Te-based materials have been known to cause environmental pollution problems, as well as the need for higher sensitivity and lower manufacturing costs, so organic dyes have been used instead of Te-based materials. Proposals and reports about recording media using recording layers made of organic materials are increasing.

この有機系材料に用いる色素としては、シアニン系色素
類（例えば特開昭５８−１１４９８９号公報）、金属錯
体（例えば特開昭５８−１６８８８号公報）等が提案さ
れている。As dyes for use in this organic material, cyanine dyes (eg, JP-A-58-114989), metal complexes (eg, JP-A-58-16888), and the like have been proposed.

しかしながら、これらの化合物は薄膜状態での空気中の
保存に対して不安定であるため、種々の安定化方法（例
えば特開昭５９−５５７９４号公報）が提案されてふり
、いまなお改良がつづけられている。However, since these compounds are unstable when stored in the air in a thin film state, various stabilization methods have been proposed (for example, Japanese Patent Application Laid-Open No. 59-55794), and improvements are still being made. It is being

またＪ、　　Ｃｈｅｍ、　　Ｓａｃ、　　Ｐｅｒｋｉｎ
　Ｔｒａｎｓ、　　Ｕ、　　８１５（１９８７）　　に
は下記式（Ａ）で示される化合物が記載されているが、
該化合物は、薄膜状態での吸収及び反射極大波長が、半
導体レーザーの発振波長とずれており、光情報記録媒体
として有用でない。Also J, Chem, Sac, Perkin
Trans, U, 815 (1987) describes a compound represented by the following formula (A),
The absorption and reflection maximum wavelengths of this compound in a thin film state are different from the oscillation wavelength of a semiconductor laser, so that it is not useful as an optical information recording medium.

ＣＣＮ 、／ しＮ （式中、Ｒ，、Ｒ２＝Ｃ）Ｉ、、　Ｃ２）１．、　ｎ−
Ｃ，）Ｉ、　ｎ−Ｃ，Ｈ，。CCN , / N (in the formula, R,, R2=C) I,, C2) 1. , n-
C,)I, n-C,H,.

Ｃ，）１．叶、　Ｃ２Ｈ，ＣＮ５Ｒ，＝Ｈ，ＮＨＡｃ　
）〈発明が解決しようとする問題点〉 本発明は、半導体レーザー光に対する吸収及び反射が太
き（、しかも光、熱等に対して安定な光情報記録媒体を
提供しようとするものである。C,)1. Kano, C2H,CN5R,=H,NHAc
) <Problems to be Solved by the Invention> The present invention aims to provide an optical information recording medium that has strong absorption and reflection of semiconductor laser light (and is stable against light, heat, etc.).

く問題点を解決するための手段） 本発明者らは上記の欠点を改良すべく鋭意検討を行った
結果、下記−最大（１）　　で示される化合物が安定で
あり、特に記録材料として有用であることを見い出し本
発明を完成するに至った。The present inventors have conducted extensive studies to improve the above-mentioned drawbacks, and have found that the compounds shown in (1) below are stable and particularly useful as recording materials. This discovery led to the completion of the present invention.

を表す。represents.

ここで、Ｒ１〜Ｒ４はそれぞれ独立して水素原子、置換
されてもよいアルキル基、置換されてもよいアルコキシ
基、ハロゲン原子、ニトロ基、シアノ−ＮＨＣ−１−Ｃ
ＮＨ−１−ＮＨＣＯ−１１１１ＩＩ −ＮＨＣＮＨ−１−ＮＨ３Ｏ２−１ −Ｓｏ、ＮＨ−１−ＳＯ２−１−Ｃ−１−ＯＣ−２子、
置換されてもよいアルキル基、置換されてもよいアリー
ル基、複素環残基またはシクロヘキシル基を表す。Ｒ，
、Ｒ６はそれぞれ独立に水素原子、置換されていてもよ
いアルキル基、置換されてもよいアリール基またはシク
ロヘキシル基を表す。Here, R1 to R4 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, a halogen atom, a nitro group, a cyano-NHC-1-C
NH-1-NHCO-1111II -NHCNH-1-NH3O2-1 -So, NH-1-SO2-1-C-1-OC-2,
Represents an optionally substituted alkyl group, an optionally substituted aryl group, a heterocyclic residue, or a cyclohexyl group. R,
, R6 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or a cyclohexyl group.

また、Ｒ３、Ｒ６は環を形成していてもよく、さらにヘ
テロ原子を含んで環を形成してもよい。Further, R3 and R6 may form a ring, or may further contain a hetero atom to form a ring.

Ｒ１は置換されてもよいアルコキシ基、ヒドロキシ基、
ハロゲン原子、シアノ基又は−ＱＣ−Ｒ”ＩＩ を表し、Ｒ”は置換されていてもよいアルキル基を表し
、Ｒ６は水素原子、置換されてもよいアルギル基、置換
されてもよいアルコキシ基、ハロゲン原子を表す。Ｒｊ
””’Ｒ１１は水素原子またはアルキル基を表す。〉 本発明の前記一般式＜１）で示される化合物は一般式（
ＩＦ） い （式中、Ｒ５−Ｒ４はそれぞれ独立して水素原子、置換
されてもよいアルキル基、置換されてもよいアルコキシ
基、ハロゲン原子、ニトロ基、シアノ基、−Ａ−Ｒまた
は−Ｂ・　　　を表し、−ＡｍはＲ″ −ＮＨＣ−１−ＣＮＨ−１−ＮＨＣ〇−１１１ＩＩ　　
　　　　　　ＩＩ −ＮＨＣＮＨ−１−ＮＨ３Ｏ２−１ −５０２ＮＨ−１５０２−１−ｃ−１−〇〇−１−ＯＣ
Ｏ−または一〇〇−を表し、 １１　　　　　　　ＩＩ ＯＱ を表わし、Ｒ，Ｒ’　はそれぞれ独立して、水素原子、
置換されてもよいアルキル基、置換されてもよいアリー
ル基、複素環残基またはシクロヘキシル基を表す。〉 で表される化合物と、一般式（ＩＩ［）Ｘ−Ｎ＝Ｏ、（
Ｉ［Ｉ） 〈式中、Ｘは を表す。R1 is an optionally substituted alkoxy group, hydroxy group,
represents a halogen atom, a cyano group, or -QC-R"II, R" represents an optionally substituted alkyl group, R6 is a hydrogen atom, an optionally substituted argyl group, an optionally substituted alkoxy group, Represents a halogen atom. Rj
""'R11 represents a hydrogen atom or an alkyl group. > The compound represented by the general formula <1) of the present invention is represented by the general formula (
IF) (wherein R5-R4 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, a halogen atom, a nitro group, a cyano group, -AR or -B -Am represents R''-NHC-1-CNH-1-NHC〇-111II
II -NHCNH-1-NH3O2-1 -502NH-1502-1-c-1-〇〇-1-OC
represents O- or 100-, represents 11 II OQ, and R and R' each independently represent a hydrogen atom,
Represents an optionally substituted alkyl group, an optionally substituted aryl group, a heterocyclic residue, or a cyclohexyl group. 〉 A compound represented by the general formula (II[)X-N=O, (
I [I) <In the formula, X represents.

ここで、Ｒ５、Ｒ，はそれぞれ独立に水素原子、置換さ
れていてもよいアルキル基、置換されてもよいアリール
基またはシクロヘキシル基を表す。Here, R5 and R each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or a cyclohexyl group.

また、ＲいＲ６は環を形成していてもよく、さらにヘテ
ロ原子を含んで環を形成してもよい。Further, R6 may form a ring, or may further contain a hetero atom to form a ring.

Ｒ１は置換されてもよいアルコキシ基、ヒドロキシ基、
ハロゲン原子、シアン基又は−〇Ｃ−Ｒ”を表し、Ｒ″
は置換されていてもよいアルキル基を表し、Ｒ８は水素
原子、置換されてもよいアルキル基、置換されてもよい
アルコキシ基、ノ＼ロゲン原子を表す。ＲＩＱ〜Ｒ１２
は水素原子またはアルキル基を表す。） で表される化合物を縮合反応させることによって製造で
きる。R1 is an optionally substituted alkoxy group, hydroxy group,
Represents a halogen atom, cyan group or -〇C-R'', R''
represents an optionally substituted alkyl group, and R8 represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, or a halogen atom. RIQ~R12
represents a hydrogen atom or an alkyl group. ) It can be produced by condensation reaction of the compound represented by.

前記縮合反応は不活性有機溶媒、例えば、メタノール、
エタノール、ｎ−プロパツール、酢酸、無水酢酸、トル
エン、クロロベンゼン、クロロホルム、ジメチルホルム
アミド、Ｎ−メチルピロリドン、ジメチルスルホキシド
、スルホラン、アセトニトリル等中において実施される
。The condensation reaction is carried out in an inert organic solvent, such as methanol,
It is carried out in ethanol, n-propertool, acetic acid, acetic anhydride, toluene, chlorobenzene, chloroform, dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, sulfolane, acetonitrile, and the like.

一般式（ＩＩ）の化合物及び一般式（ＩＩＩ）の化合物
を前記溶媒中で混合し、更に触媒、特にピペリジン、ピ
リジン、トリエチルアミンもしくはピペリジンと氷酢酸
との混合液のような有機塩基を加え、０〜１００℃、好
ましくは２０〜８０℃で０．５〜１０時間、好ましくは
１〜５時間反応させる。ついで反応混合物を冷却し、濾
過することで、一般式（Ｉ）　　で示される本発明の化
合物の粗ケーキが得られる。粗ケーキの精製は適当な溶
媒からの再結晶等により行うことができる。A compound of general formula (II) and a compound of general formula (III) are mixed in the above-mentioned solvent, and a catalyst, especially an organic base such as piperidine, pyridine, triethylamine or a mixture of piperidine and glacial acetic acid is added, The reaction is carried out at ~100°C, preferably 20-80°C, for 0.5-10 hours, preferably 1-5 hours. The reaction mixture is then cooled and filtered to obtain a crude cake of the compound of the invention represented by general formula (I). The crude cake can be purified by recrystallization from an appropriate solvent.

〈発明の効果〉 本発明の新規なアザメチン系化合物の薄膜は、７００ｎ
ｍ〜８５０ｎｍの領域に吸収極大波長を有し、また７５
０ｎｍ〜８５０ｎｍの領域で高い反射率を有して−する
ため、種々の用途、特に光情報記録媒体として有用であ
る。<Effects of the Invention> The thin film of the novel azamethine compound of the present invention has a thickness of 700 nm.
It has a maximum absorption wavelength in the region of 75 nm to 850 nm, and
Since it has a high reflectance in the range of 0 nm to 850 nm, it is useful for various purposes, especially as an optical information recording medium.

〈実施例〉 以下実施例により具体的説明を行うが、本発明はこれに
限定されるものではない。<Examples> The present invention will be specifically explained below using examples, but the present invention is not limited thereto.

なお、実施例においてスペクトルの測定は島津製作所ｔ
ｌＶ−３６５型分光光度計を用い、基板側より光を照射
して測定を行った。また膜厚測定はティラー、ホブソン
社製タリステップ膜厚計を用いた。In addition, in the examples, the measurement of spectra was carried out by Shimadzu Corporation.
The measurement was performed using a LV-365 spectrophotometer and irradiating light from the substrate side. Further, the film thickness was measured using a Talystep film thickness meter manufactured by Tiller and Hobson.

実施例　１ １．３−ビスジシアノビニルインダン１．５０ｇ　とで
示される化合物２．５０ｇを無水酢酸４〇−中で混合し
、２０〜２５℃で５時間撹拌した。そしてこの混合液を
濾過し、水冷メタノールで洗浄し、乾燥した。Example 1 1.50 g of 1.3-bisdicyanovinyl indane and 2.50 g of the compound represented by 1.3-bisdicyanovinyl indane were mixed in 40% of acetic anhydride and stirred at 20 to 25°C for 5 hours. The mixture was then filtered, washed with water-cooled methanol, and dried.

クロロホルムより再結晶し、下記式（２）に示される化
合物の精製ケーキ１．８０ｇが得られた。Recrystallization from chloroform yielded 1.80 g of a purified cake of the compound represented by the following formula (2).

収率６７．３％。融点３００℃以上。アセトン溶液中の
吸光度は、λｍａｘ：　７１Ｑｎｍ、　　ｔ：　３．９
５Ｘ１０’。Yield 67.3%. Melting point 300℃ or higher. The absorbance in the acetone solution is λmax: 71Qnm, t: 3.9
5X10'.

ＣＣＮ ／ ＣＮ 実施例２ １．３−ビスジンアノビニルインダン１．５０ｇ　とで
示される化合物３．８１ｇを無水酢酸４〇−中で混合し
、２１〜２５℃で８時間撹拌した。そしてこの混合液を
濾過し、水冷メタノールで洗浄し、乾燥した。CCN/CN Example 2 1.50 g of 1.3-bisdineanovinylindane and 3.81 g of the compound represented by the formula were mixed in 40% of acetic anhydride and stirred at 21 to 25°C for 8 hours. The mixture was then filtered, washed with water-cooled methanol, and dried.

クロロホルムより再結晶し、下記式（４）に示される化
合物の精製ケーキ２．０６ｇが得られた。Recrystallization from chloroform gave 2.06 g of a purified cake of the compound represented by the following formula (4).

収率６３．２％。融点２４７〜２４９℃。アセトン溶液
中の吸光度は、λｍａｘ：　７１５ｎｍ、　　ｇ：　４
．６１Ｘ１０’　。Yield 63.2%. Melting point 247-249°C. The absorbance in the acetone solution is λmax: 715 nm, g: 4
．． 61X10'.

い 実施例３〜４５ 以下、実施例１又は実施例２と同様の方法によって、以
下の表−１に示す化合物が得られた。Examples 3 to 45 The compounds shown in Table 1 below were obtained in the same manner as in Example 1 or 2.

実施例４６ ガラス基板上に実施例１で得られた化合物のトリクロロ
エチレン溶液を２０００ｒｐｍ　ｘ　２Ｑｓｅｃの条件
で回転塗布して厚さ８００人の記録層を形成し、光情報
記録媒体を作成した。得られた記録媒体の透過率及び反
射率曲線を第１図に示す。Example 46 A trichlorethylene solution of the compound obtained in Example 1 was spin-coated on a glass substrate at 2000 rpm x 2 Qsec to form a recording layer with a thickness of 800 layers, thereby producing an optical information recording medium. The transmittance and reflectance curves of the obtained recording medium are shown in FIG.

この記録媒体に発振波長８３０ｎｍの半導体レーザーを
用いスポット径１μｍとし４０ｍＪ／ａｍで照射を行っ
たところ明瞭なスポットの形成が認められた。When this recording medium was irradiated with a semiconductor laser having an oscillation wavelength of 830 nm and a spot diameter of 1 μm at a rate of 40 mJ/am, the formation of a clear spot was observed.

実施例４７ ガラス基板上に実施例２で得られた化合物のクロロホル
ム溶液を２０００ｒｐｍ　ｘ　２０ｓｅｃの条件で回転
塗布して厚さ７００人の記録層を形成し、光情報記録媒
体を作成した。得られた記録媒体の透過率及び反射率曲
線を第２図に示す。Example 47 A chloroform solution of the compound obtained in Example 2 was spin-coated on a glass substrate under conditions of 2000 rpm x 20 sec to form a recording layer with a thickness of 700 mm, thereby producing an optical information recording medium. FIG. 2 shows the transmittance and reflectance curves of the obtained recording medium.

この記録媒体に発振波長８３０ｎｍの半導体レーザーを
用いスポット径１μｍとし４０ｍＪ／ｃｄで照射を行っ
たところ明瞭なスポットの形成が認められた。When this recording medium was irradiated with a semiconductor laser with an oscillation wavelength of 830 nm and a spot diameter of 1 μm at 40 mJ/cd, the formation of a clear spot was observed.

比較例１　′ ガラス基板上に下記構造式の化合物のクロロホルム溶液
を２０００ｒｐｍ　ｘ　２Ｑｓｅｃの条件で回転塗布し
て厚さ７００人の記録層を形成し、光情報記録媒体を作
成した。得られた記録媒体の透過率及び反射率曲線を第
３図に示す。第３図に示される通り、半導体レーザーの
発振波長領域であまり高い反射率を有していない。Comparative Example 1' A chloroform solution of a compound having the following structural formula was spin-coated on a glass substrate at 2000 rpm x 2 Qsec to form a recording layer with a thickness of 700 mm, thereby producing an optical information recording medium. The transmittance and reflectance curves of the obtained recording medium are shown in FIG. As shown in FIG. 3, it does not have a very high reflectance in the oscillation wavelength region of a semiconductor laser.

ＣＣＮ ＼７ノ いCCN \7ノ stomach

【図面の簡単な説明】[Brief explanation of the drawing]

第１図は実施例４６で得られた記録媒体の透過率曲線及
び反射率曲線を示す。 第２図は実施例４７で得られた記録媒体の透過率曲線及
び反射率曲線を示す。 第３図は比較例１で得られた記録媒体の透過率曲線及び
反射率曲線を示す。 （％）　　第１図 （ｎｍ） （％）　　第２図FIG. 1 shows the transmittance curve and reflectance curve of the recording medium obtained in Example 46. FIG. 2 shows the transmittance curve and reflectance curve of the recording medium obtained in Example 47. FIG. 3 shows the transmittance curve and reflectance curve of the recording medium obtained in Comparative Example 1. (%) Figure 1 (nm) (%) Figure 2

Claims (3)

【特許請求の範囲】[Claims] （１）一般式（ I ） ▲数式、化学式、表等があります▼（ I ） （式中、Ｘは ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼ を表す。 ここで、Ｒ＿１〜Ｒ＿４はそれぞれ独立して水素原子、
置換されてもよいアルキル基、置換されてもよいアルコ
キシ基、ハロゲン原子、ニトロ基、シアノ基、ヒドロキ
シ基、置換されてもよいアミノ基、−Ａ−Ｒまたは▲数
式、化学式、表等があります▼を表し、−Ａ−は ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、 ▲数式、化学式、表等があります▼、−ＮＨＳＯ＿２−
、 −ＳＯ＿２ＮＨ−、−ＳＯ＿２−、▲数式、化学式、表
等があります▼、▲数式、化学式、表等があります▼、
▲数式、化学式、表等があります▼または▲数式、化学
式、表等があります▼を表し、 ▲数式、化学式、表等があります▼は▲数式、化学式、
表等があります▼または▲数式、化学式、表等がありま
す▼ を表わし、Ｒ、Ｒ′それぞれ独立して、水素原子、置換
されてもよいアルキル基、置換されてもよいアリール基
、複素環残基またはシクロヘキシル基を表す。Ｒ＿５、
Ｒ＿６はそれぞれ独立に水素原子、置換されていてもよ
いアルキル基、置換されてもよいアリール基またはシク
ロヘキシル基を表す。 また、Ｒ＿５、Ｒ＿６は環を形成していてもよく、さら
にヘテロ原子を含んで環を形成してもよい。 Ｒ＿７は置換されてもよいアルコキシ基、ヒドロキシ基
、ハロゲン原子、シアノ基又は▲数式、化学式、表等が
あります▼ を表し、Ｒ″は置換されていてもよいアルキル基を表し
、Ｒ＿８は水素原子、置換されてもよいアルキル基、置
換されてもよいアルコキシ基又はハロゲン原子を表す。 Ｒ＿９〜Ｒ＿１＿１は水素原子またはアルキル基を表す
。）で表わされるアザメチン系化合物。(1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents. Here, R_1 to R_4 are each independently a hydrogen atom,
There are optionally substituted alkyl groups, optionally substituted alkoxy groups, halogen atoms, nitro groups, cyano groups, hydroxy groups, optionally substituted amino groups, -AR or ▲ mathematical formulas, chemical formulas, tables, etc. ▼ represents ▲, and -A- represents ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -NHSO_2-
, -SO_2NH-, -SO_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼.
Tables, etc. ▼ or ▲ Numerical formulas, chemical formulas, tables, etc. ▼ represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, a heterocyclic residue group or cyclohexyl group. R_5,
R_6 each independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or a cyclohexyl group. Furthermore, R_5 and R_6 may form a ring, or may further contain a hetero atom to form a ring. R_7 represents an optionally substituted alkoxy group, hydroxy group, halogen atom, cyano group, or ▲There are numerical formulas, chemical formulas, tables, etc.▼, R'' represents an optionally substituted alkyl group, and R_8 is a hydrogen atom , represents an optionally substituted alkyl group, an optionally substituted alkoxy group, or a halogen atom; R_9 to R_1_1 represent a hydrogen atom or an alkyl group). （２）一般式（II） ▲数式、化学式、表等があります▼（II） （式中、Ｒ＿１〜Ｒ＿４はそれぞれ独立して水素原子、
置換されてもよいアルキル基、置換されてもよいアルコ
キシ基、ハロゲン原子、ニトロ基、シアノ基、ヒドロキ
シ基、置換されてもよいアミノ基、−Ａ−Ｒまたは▲数
式、化学式、表等があります▼を表し、−Ａ−は ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、 ▲数式、化学式、表等があります▼、−ＮＨＳＯ＿２−
、 −ＳＯ＿２ＮＨ−、−ＳＯ＿２−、▲数式、化学式、表
等があります▼、▲数式、化学式、表等があります▼、
▲数式、化学式、表等があります▼または▲数式、化学
式、表等があります▼を表し、 ▲数式、化学式、表等があります▼は▲数式、化学式、
表等があります▼または▲数式、化学式、表等がありま
す▼ を表わし、Ｒ、Ｒ′はそれぞれ独立して、水素原子、置
換されてもよいアルキル基、置換されてもよいアリール
基、複素環残基またはシクロヘキシル基を表す。） で表される化合物と、一般式（III） Ｘ−Ｎ＝Ｏ（III） （式中、Ｘは ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼ を表す。ここで、Ｒ＿５、Ｒ＿６はそれぞれ独立に、水
素原子、置換されていてもよいアルキル基、置換されて
もよいアリール基またはシクロヘキシル基を表す。また
、Ｒ＿５、Ｒ＿６は環を形成していてもよく、さらにヘ
テロ原子を含んで環を形成してもよい。 Ｒ＿７は置換されてもよいアルコキシ基、ヒドロキシ基
、ハロゲン原子、シアノ基又は▲数式、化学式、表等が
あります▼ を表し、Ｒ″は置換されていてもよいアルキル基を表し
、Ｒ＿８は水素原子、置換されてもよいアルキル基、置
換されてもよいアルコキシ基又はハロゲン原子を表す。 Ｒ＿９〜Ｒ＿１＿１は水素原子またはアルキル基を表す
。）で表される化合物とを反応させることを特徴とする
一般式（ I ） ▲数式、化学式、表等があります▼（ I ） （式中、Ｘ、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４は前記の
意味を有する）で表わされるアザメチン系化合物の製法
。(2) General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, R_1 to R_4 are each independently a hydrogen atom,
There are optionally substituted alkyl groups, optionally substituted alkoxy groups, halogen atoms, nitro groups, cyano groups, hydroxy groups, optionally substituted amino groups, -AR or ▲ mathematical formulas, chemical formulas, tables, etc. ▼ represents ▲, and -A- represents ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -NHSO_2-
, -SO_2NH-, -SO_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼.
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. Represents a residue or a cyclohexyl group. ) and the general formula (III) X-N=O(III) (wherein,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents. Here, R_5 and R_6 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or a cyclohexyl group. Furthermore, R_5 and R_6 may form a ring, or may further contain a hetero atom to form a ring. R_7 represents an optionally substituted alkoxy group, hydroxy group, halogen atom, cyano group, or ▲There are numerical formulas, chemical formulas, tables, etc.▼, R'' represents an optionally substituted alkyl group, and R_8 is a hydrogen atom , represents an optionally substituted alkyl group, an optionally substituted alkoxy group, or a halogen atom; R_9 to R_1_1 represent a hydrogen atom or an alkyl group). Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) A method for producing an azamethine compound represented by (in the formula, X, R_1, R_2, R_3, R_4 have the above meanings). （３）基盤上に直接または下引き層を介して記録層を設
け、さらにその上に必要に応じて保護層を設けてなる光
情報記録媒体において、前記記録層が少なくとも下記一
般式（ I ）で表される化合物を一種以上含むことを特
徴とする光情報記録媒体。 ▲数式、化学式、表等があります▼（ I ） （式中、Ｘは ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼ を表す。 ここで、Ｒ＿１〜Ｒ＿４はそれぞれ独立して水素原子、
置換されてもよいアルキル基、置換されてもよいアルコ
キシ基、ハロゲン原子、ニトロ基、シアノ基、ヒドロキ
シ基、置換されてもよいアミノ基、−Ａ−Ｒまたは▲数
式、化学式、表等があります▼を表し、−Ａ−は ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、 ▲数式、化学式、表等があります▼、−ＮＨＳＯ＿２−
、 −ＳＯ＿２ＮＨ−、−ＳＯ＿２−、▲数式、化学式、表
等があります▼、▲数式、化学式、表等があります▼、
▲数式、化学式、表等があります▼または▲数式、化学
式、表等があります▼を表し、 ▲数式、化学式、表等があります▼は▲数式、化学式、
表等があります▼または▲数式、化学式、表等がありま
す▼ を表わし、Ｒ、Ｒ′はそれぞれ独立して、水素原子、置
換されてもよいアルキル基、置換されてもよいアリール
基、複素環残基またはシクロヘキシル基を表す。Ｒ＿５
、Ｒ＿６はそれぞれ独立に水素原子、置換されてもよい
アルキル基、置換されてもよいアリール基またはシクロ
ヘキシル基を表す。また、Ｒ＿５、Ｒ＿６は環を形成し
ていてもよく、さらにヘテロ原子を含んで環を形成して
もよい。 Ｒ＿７は置換されてもよいアルコキシ基、ヒドロキシ基
、ハロゲン原子、シアノ基又は▲数式、化学式、表等が
あります▼ を表し、Ｒ″は置換されていてもよいアルキル基を表し
、Ｒ＿８は水素原子、置換されてもよいアルキル基、置
換されてもよいアルコキシ基又はハロゲン原子を表す。 Ｒ＿９〜Ｒ＿１＿１は水素原子又はアルキル基を表す。 ）(3) In an optical information recording medium in which a recording layer is provided on a substrate directly or via an undercoat layer, and a protective layer is further provided thereon as necessary, the recording layer has at least the following general formula (I). An optical information recording medium characterized by containing one or more compounds represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents. Here, R_1 to R_4 are each independently a hydrogen atom,
There are optionally substituted alkyl groups, optionally substituted alkoxy groups, halogen atoms, nitro groups, cyano groups, hydroxy groups, optionally substituted amino groups, -AR or ▲ mathematical formulas, chemical formulas, tables, etc. ▼ represents ▲, and -A- represents ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -NHSO_2-
, -SO_2NH-, -SO_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼.
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. Represents a residue or a cyclohexyl group. R_5
, R_6 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or a cyclohexyl group. Furthermore, R_5 and R_6 may form a ring, or may further contain a hetero atom to form a ring. R_7 represents an optionally substituted alkoxy group, hydroxy group, halogen atom, cyano group, or ▲There are numerical formulas, chemical formulas, tables, etc.▼, R'' represents an optionally substituted alkyl group, and R_8 is a hydrogen atom , represents an optionally substituted alkyl group, an optionally substituted alkoxy group, or a halogen atom. R_9 to R_1_1 represent a hydrogen atom or an alkyl group.)
JP62325998A 1987-04-14 1987-12-22 Azamethine compound, production thereof and optical information recording medium using said compound Pending JPH01165565A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP62325998A JPH01165565A (en) 1987-12-22 1987-12-22 Azamethine compound, production thereof and optical information recording medium using said compound
US07/179,251 US5028708A (en) 1987-04-14 1988-04-08 Azamethinyl quinoline derivatives
DE88303379T DE3883583T2 (en) 1987-04-14 1988-04-14 Azamethine compounds, process for their preparation and an agent using them for recording optical information.
EP88303379A EP0287377B1 (en) 1987-04-14 1988-04-14 Azamethine compounds, process for preparing the same and a medium for recording optical information using such compounds
US07/383,081 US5061796A (en) 1987-04-14 1989-07-21 Azamethine compounds
US07/684,290 US5136054A (en) 1987-04-14 1990-04-12 Sulfone-containing azamethine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP62325998A JPH01165565A (en) 1987-12-22 1987-12-22 Azamethine compound, production thereof and optical information recording medium using said compound

Publications (1)

Publication Number Publication Date
JPH01165565A true JPH01165565A (en) 1989-06-29

Family

ID=18182956

Family Applications (1)

Application Number Title Priority Date Filing Date
JP62325998A Pending JPH01165565A (en) 1987-04-14 1987-12-22 Azamethine compound, production thereof and optical information recording medium using said compound

Country Status (1)

Country Link
JP (1) JPH01165565A (en)

Similar Documents

Publication Publication Date Title
TWI397561B (en) Anthocyanin compounds and optical recording materials
WO2006011306A1 (en) Optical recording material and optical recording medium
KR101027229B1 (en) Cyanine compounds, optical recording materials and optical recording media
CN101031544B (en) Heterocyclic compounds and optical recording materials
JP2008274291A (en) Bis-styryl dye, its production process and its application for high-density optical recording medium
JP3860616B2 (en) Phthalocyanine compounds
JP2687566B2 (en) Novel tetraazaporphin, method for producing the same, optical recording medium using the same, and method for producing the optical recording medium
EP0823432B1 (en) Phthalocyanine compounds and their use as rewritable optical recording material
AU1890901A (en) Squarylium compounds and optical recording media made by using the same
EP0287377B1 (en) Azamethine compounds, process for preparing the same and a medium for recording optical information using such compounds
TWI436979B (en) Indolium (INDOLIUM) compound and an optical recording material using the same
KR101272743B1 (en) Cyanine compound, optical recording material utilizing the compound, and optical recording medium
JPH02147664A (en) Naphthalocyanine derivative, its production, optical recording medium prepared by using same and production of optical recording medium
US4882428A (en) Azaporphyrin compounds
KR20090047386A (en) Bridged cyanine compounds and optical recording materials containing the same
JPH01165565A (en) Azamethine compound, production thereof and optical information recording medium using said compound
JPH0624146A (en) Infrared absorption compound and optical recording medium using said compound
TWI412033B (en) Optical recording materials and anthocyanin compounds
JP2547033B2 (en) Methine compound, method for producing the same and optical information recording medium using the same
JPH0215072A (en) Condensation compound, its production and optical information recording medium
JPH01178494A (en) Optical recording medium
JPH01157944A (en) Methine compound, its production and optical information recording medium made thereof
TWI383896B (en) Optical recording materials, chalcone compounds and metal complexes
JP3863195B2 (en) Phthalocyanine compounds
TWI407434B (en) An optical recording material and an optical recording medium including the same