JPH0232164A - Alpha-cyanoazomethine-based compound, production thereof and optical information recording medium using said compound - Google Patents
Alpha-cyanoazomethine-based compound, production thereof and optical information recording medium using said compoundInfo
- Publication number
- JPH0232164A JPH0232164A JP63182436A JP18243688A JPH0232164A JP H0232164 A JPH0232164 A JP H0232164A JP 63182436 A JP63182436 A JP 63182436A JP 18243688 A JP18243688 A JP 18243688A JP H0232164 A JPH0232164 A JP H0232164A
- Authority
- JP
- Japan
- Prior art keywords
- tables
- formulas
- chemical formulas
- mathematical
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 230000003287 optical effect Effects 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- PXNJGLAVKOXITN-UHFFFAOYSA-N 2-(4-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=C(CC#N)C=C1 PXNJGLAVKOXITN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract description 6
- 238000010521 absorption reaction Methods 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 239000004065 semiconductor Substances 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- -1 piperidine Chemical class 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- QILKKAFYAFEWGU-UHFFFAOYSA-N 4-(cyanomethyl)benzonitrile Chemical compound N#CCC1=CC=C(C#N)C=C1 QILKKAFYAFEWGU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000000985 reflectance spectrum Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 101150030723 RIR2 gene Proteins 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/382—Contact thermal transfer or sublimation processes
- B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
- B41M5/39—Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine
Abstract
Description
【発明の詳細な説明】
〈産業との利用分骨〉
本発明は、α−シアノアゾメチン系化合物、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 Applications> The present invention relates to an α-cyanoazomethine compound, a method for producing the same, and an optical information recording medium using the same.
〈従来の技術〉
゛ 光情報記録媒体は媒体
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
、種々の光情報記録媒体の開発研究が行われている。<Prior art> ゛ Since optical information recording media have non-contact between the medium and the writing or reading head,
The recording medium has a characteristic that it does not deteriorate due to wear and tear, and for this reason, research and development of various optical information recording media are being conducted.
このような光情報記録媒体のうち、暗室による現像処理
が不要である等の点で、ヒートモード光情報記録媒体の
開発が活発になっている。Among such optical information recording media, heat mode optical information recording media are being actively developed because they do not require development in a dark room.
このヒートモードの光記録媒体は、記録光を熱として利
用する光情報記録媒体であり、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。This heat mode optical recording medium is an optical information recording medium that uses recording light as heat. For example, a part of the medium is melted or removed using a recording light such as a laser to form a pit. There is a pit-forming type in which writing is performed by forming small holes, recording information using the pits, and reading by detecting the pits with a readout light.
したがって、光情報記録媒体は、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 information recording media must absorb the energy of laser light efficiently, so they must have high absorption of laser light of a specific wavelength used for recording, and must be used for reproduction in order to accurately reproduce information. It is necessary that the reflectance for laser light of a specific wavelength is high.
このようなピ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。Up to now, most of these pit-forming type recording media, particularly those using a semiconductor laser as a light source, which can reduce the size of 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
１ｆｉ（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 to be used in this organic material, cyanine dyes 1fi (eg, JP-A-58-114989), metal complexes (eg, JP-A-58-16888), and the like have been proposed.
〈発明が解決しようとする１２１ ｍ ＞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、濡々の安定化方法（例えば特開昭８
Ｂ−８１７９２号公報）が提案されており、いまなお
改良がつづけられている。<121 m to be solved by the invention> However, since these compounds are unstable when stored in the air in a thin film state, wet stabilization methods (for example, JP-A No. 8
B-81792) has been proposed, and improvements are still being made.
本発明は、半導体レーザー光に対する吸収及び反射が大
きく、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。The present invention aims to provide an optical information recording medium that has high absorption and reflection of semiconductor laser light and is stable against light, heat, and the like.
く課題を解決するための手段〉
本発明者らはｔ記の欠点を改良すべ（鋭意検討を行った
結果、下記−数式（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。Means for Solving the Problems The present inventors have found that the compound represented by the following formula (1) is stable and particularly useful as a recording material. This discovery led to the completion of the present invention.
ＣＮ
−ＮＨＣＯ−
Ｃ−
一〇〇−
を表わす。ここでＲ１，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、置換されていても
よいアリール基またはシクロヘキシル基を表す。また、
Ｒ，、Ｒ，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。 Ｒａは置換されてい
てもよいアルキル基、置換されていてもよいアルコキレ
Ｒ，Ｒ’はそれぞれ独立して、水素原子、置換されてい
てもよいアルキル基、置換されていてもよいアリール基
を表す。 Ｒ４は水素原子、置換されていてもよいアル
キル基、置換されていてもよいアルコキレ基、ヒドロキ
レ基、ハロゲン表わし、Ｒ，Ｒ’はそれぞれ独立して、
水素原子、置換されていてもよいアルキル基、置換され
ていてもよいアリール基を表す。Ｒ，〜Ｒ７は水素原子
またはアルキル基を表す、）ここでＲＩＲ２がアルキル
基の場合は、炭素数１〜８のものが好ましい。 Ｒａが
アルキル基又はアルコキシ基の場合は、炭素数１〜８の
ものが好ましい。CN -NHCO- C- represents 100-. Here, R1 and R each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or a cyclohexyl group. Also,
R,, R, may form a ring, and may further contain a hetero atom to form a ring. Ra is an optionally substituted alkyl group, and optionally substituted alkoxy R and R' each independently represent a hydrogen atom, an optionally substituted alkyl group, and an optionally substituted aryl group. . R4 represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkoxyl group, a hydroxyl group, or a halogen; R and R' are each independently,
Represents a hydrogen atom, an optionally substituted alkyl group, and an optionally substituted aryl group. R, to R7 represent a hydrogen atom or an alkyl group) Here, when RIR2 is an alkyl group, it preferably has 1 to 8 carbon atoms. When Ra is an alkyl group or an alkoxy group, it preferably has 1 to 8 carbon atoms.
Ｒ４については、アルキル基又はアルコキレ基の場合は
炭素数１〜４が好ましい。Ｒ，Ｒ７については、アルキ
ル基又はアルコキシ基の場合は炭素数１〜８が好ましい
、ＲａへＲ１については炭素数１〜２のアルキル基が好
ましい。Regarding R4, in the case of an alkyl group or an alkoxyl group, it preferably has 1 to 4 carbon atoms. R and R7 are preferably alkyl groups or alkoxy groups having 1 to 8 carbon atoms, and R1 to Ra is preferably an alkyl group having 1 to 2 carbon atoms.
本発明の一般式中で示される化合物は、ｐ−ニトロペン
ジルシアニ）’ 、！ニー数式（１）％式％（１）
（式中、Ｘは前記と同じ意味を示す。）で表される化合
物とを縮合反応させることによって製造できる。The compound represented by the general formula of the present invention is p-nitropendylcyani)',! It can be produced by condensation reaction with a compound represented by the following formula (1)% (1) (wherein, X has the same meaning as above).
前記縮合反応は不活性有機溶媒、例えば、エタノール、
ｎ−プロパツール、トルエン、りａ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
、ジメチルホルホキレド、スルホラン、アセトニトリル
または無水酢酸等を用いて実施される。The condensation reaction is carried out in an inert organic solvent, such as ethanol,
The reaction is carried out using n-propanol, toluene, lyalobenzene, chloroform, dimethylformamide, N-methylpyrrolidone, dimethylphorphokiledone, sulfolane, acetonitrile, acetic anhydride, or the like.
ｐ−ニトロベンジルシアニド及び前記−数式（１）で示
される化合物を前記不活性有機溶媒中で混合し、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°Ｃ１好ましくは２０〜８０°Ｃで０
５〜１０時間、好ましくは１〜５時間反応させる。p-Nitrobenzyl cyanide and the compound represented by formula (1) are mixed in the inert organic solvent, and a catalyst, particularly an organic compound such as piperidine, pyridine, triethylamine or a mixture of piperidine and glacial acetic acid, is added. Add a base and heat at 0 to 100°C, preferably 20 to 80°C.
The reaction is allowed to proceed for 5 to 10 hours, preferably for 1 to 5 hours.
ついで反応混合物を冷却し、デ過することで、−数式山
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Ｃと
ができる。The reaction mixture is then cooled and filtered to obtain a crude cake of the compound of the present invention represented by the formula . The crude cake can be purified by recrystallization from an appropriate solvent.
本発明の方法によっＣ得られるアザメチン系化合物を用
いた光情報記録媒体用途としての基本構成は第１図に示
したが、ｌｉ２図〜第４図に示すように必要に応じてさ
らに下引層、保護層などを設けることができる。また同
一構成の２枚の記録媒体を用い記録Ｍ１２を内側に対向
して配置するいわゆるエアサンドイッチ構造してもよく
、保護間４を介して接着する貼り合わせ構造としてへよ
い。情報の記録はレーザーの光の熱作用による色素膜の
形状変化によっておこなわれ、情報の再生は、形状変化
部と非形状変化部からの反射光の差を検出することによ
って行われる。The basic structure of an optical information recording medium using the azamethine compound obtained by the method of the present invention is shown in FIG. layers, protective layers, etc. may be provided. Furthermore, a so-called air sandwich structure may be used in which two recording media having the same configuration are used and the recording medium 12 is placed facing each other on the inside, or a bonded structure in which the recording media are bonded through the protective gap 4 may be used. Information is recorded by changing the shape of the pigment film due to the thermal action of laser light, and information is reproduced by detecting the difference in reflected light from the shape-changing portion and the non-shape-changing portion.
記録層の形成は蒸着または溶液塗布などの通常の手段に
よって行うことができる。また記録層は、本発明の色素
を１種または２８１以と組み合わせて形成でき、また本
発明の色素は他の色素と組み合わせて形成してもよい。The recording layer can be formed by conventional means such as vapor deposition or solution coating. Further, the recording layer can be formed by combining the dye of the present invention alone or with 281 or more, and the dye of the present invention may be formed by combining the dye of the present invention with other dyes.
すなわち混合、積層などの形態で用いることもできる。That is, they can also be used in a mixed or laminated form.
また本発明の色素は高分子材料たとえばシリコーン、ポ
リアミド系樹脂、ビニル系樹脂、天然高分子など種々の
材料或いはシリコンカップリング剤などに混合分散して
用いてもよく、また安定剤、分散剤、帯電防止剤などと
一緒に用いることもできる。Furthermore, the dye of the present invention may be used by being mixed and dispersed in various polymer materials such as silicone, polyamide resin, vinyl resin, natural polymer, or silicone coupling agent, and stabilizers, dispersants, etc. It can also be used together with an antistatic agent.
記録層の厚さは５０人〜５０００人、好ましくは１００
人〜２０００人の範囲にするのが好ましい。The thickness of the recording layer is 50 to 5000, preferably 100.
It is preferable that the number of people be in the range of 2,000 to 2,000 people.
本発明において使用される基板材料は使用するレーザー
光線に対して透明なものであり、ガラス、石英および各
種のプラスチックスなどが挙げられる。代表的なプラス
チックスとしては、ホｌ カー ホネート樹脂、塩化ビ
ニルｔａｔ＋ｍ、ポリメチルメタアクリル８１１１！（
ＰＭＭＡ）、ポリエステルｍ詣、ポリエチレン樹脂、ポ
リプロピレン樹脂、ポリアミドＳ詣、ポリスチレン樹脂
、＋Ｊ？リアミド樹脂及び工ぽキシ樹脂その他の単独重
合体及び共重合体が挙げられる。The substrate material used in the present invention is transparent to the laser beam used, and includes glass, quartz, and various plastics. Typical plastics include hol carbonate resin, vinyl chloride TAT+M, and polymethyl methacrylic 8111! (
PMMA), polyester resin, polyethylene resin, polypropylene resin, polyamide S resin, polystyrene resin, +J? Examples include lyamide resin, engineered poxy resin, and other homopolymers and copolymers.
下引き層８は、溶剤からの基板の保護、接着て、前記高
分子材料、シランカップリング剤、熱橋化合物（Ｓｉｎ
ｓ 、 ＭｇＦｚ 、 ＺｕＯなど）、紫外線硬化樹脂
、熱硬化樹脂などを用いることができる。The undercoat layer 8 protects the substrate from solvents, adheres to the substrate, and contains the polymer material, silane coupling agent, thermal linking compound (Sin
S, MgFz, ZuO, etc.), ultraviolet curing resin, thermosetting resin, etc. can be used.
下引き層の膜厚は０．１〜８０μｍ好ましくは０．２〜
１０μｍが好ましい。The thickness of the undercoat layer is 0.1 to 80 μm, preferably 0.2 to 80 μm.
10 μm is preferred.
保ｇＩ層４はｒ９れ、はこりなどからの保護、記録層の
化学的安定性の向上を目的として設けられ、下引き層と
同じ材料を使用できる。The protective gI layer 4 is provided for the purpose of protecting the recording layer from scratches and the like and improving the chemical stability of the recording layer, and can be made of the same material as the undercoat layer.
保獲層の膜厚は０．１μｍ以と好ましくは５０μｍ以と
が適当である。The thickness of the retention layer is suitably 0.1 μm or more, preferably 50 μm or more.
〈発明の効果〉
本発明になる新規なα−レアノアゾメチン系化合物の′
Ｒ膜は、５００ｎｍ〜７００ｎｍの領域に吸収極大波長
を有し、また！Ｓ ＯＱ ｎｍ−８Ｑ Ｑ ｎｍの領域
で高い反射率を有し、さらに安定性良好であるため、涌
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 novel α-leanoazomethine compounds of the present invention
The R film has a maximum absorption wavelength in the region of 500 nm to 700 nm, and! It has a high reflectance in the SOQ nm-8Q Q nm range and has good stability, so it is useful for many uses, especially as an optical information recording medium.
本発明の化合物の用途としては、他に、カラー ｔｅ
ａ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、光学フィルター用、有機先導ター用、染色１１１な
どがあげられる。Other uses of the compounds of the present invention include color te
Examples include fine color separation filters for A elements and color displays, optical filters, organic leaders, and dyeing 111.
〈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.
実施例１
ｐ−シアノベンジＪレシアニ３ｒドｔ、ｏｏＩＩと下記
式（１）
で示される化合物１．６’ｒｌをメチルアルコール６０
−中で混合し、２０〜２８°Ｃで５時間攪拌した。そし
てこの混合液を６°Ｃに冷却し、濾過することで粗ケー
キが得られた。Example 1 p-cyanobendiJreciani 3rdot,ooII and 1.6'rl of the compound represented by the following formula (1) were mixed with 60% methyl alcohol.
- and stirred at 20-28°C for 5 hours. The mixture was then cooled to 6°C and filtered to obtain a crude cake.
トルエンより再結晶し、下式（２）で示される化合物の
精製ケーキ１．９２Ｎが得られた。融点１９８〜１９５
’Ｏ，、アセトン溶液中の吸光度はλｍａＸ ：５４５
ｎｍ、ｔ ：４．６９Ｘ１０゜実施例２
ｐ−シアノベンジルレアニド１．００ｆと下記式（８）
ｐ−シアノベンジルシアニド１．００ｇと下記式（５）
で示される化合物１．７’Ｍをメチルアルコール７０１
ｄ中で混合【ハ２０〜２８°Ｃで６時間攪拌した。そし
てこの混合液を５°Ｃに冷却し、濾過することで粗ケー
キが得られた。Recrystallization from toluene yielded a 1.92N purified cake of the compound represented by the following formula (2). Melting point 198-195
'O,, the absorbance in acetone solution is λmaX: 545
nm, t: 4.69X10° Example 2 1.00 f of p-cyanobenzyl cyanide and the following formula (8) 1.00 g of p-cyanobenzyl cyanide and 1.7'M of the compound represented by the following formula (5) Methyl alcohol 701
The mixture was stirred at 20-28°C for 6 hours. The mixture was cooled to 5°C and filtered to obtain a crude cake.
エチルアルコールより再結晶し、下記式（４）で示され
る化合物の精製ケーキ２．１２１が得られた。融点１８
１〜１８２”Ｃｏアセトン溶液中の吸光度はλｍａｘ
： ５４４ ｎｍ、ε：４．９８×１０４
で示される化合物１．８７１をメチルアルコール７０−
中で混合し、２０〜２８°Ｃで７時間攪拌した。そして
この混合液を５゛Ｃに冷却し、濾過することで粗ケーキ
が得られた。Recrystallization from ethyl alcohol yielded purified cake 2.121 of the compound represented by the following formula (4). Melting point 18
1-182” The absorbance in Co acetone solution is λmax
: 544 nm, ε: 4.98×104 Compound 1.871 was mixed with methyl alcohol 70-
and stirred for 7 hours at 20-28°C. The mixture was cooled to 5°C and filtered to obtain a crude cake.
エチルアルコールより再結晶し、下記式（６）で示され
る化合物のｍａケーキ１．６８Ｎが得られた。融点１７
２〜１７４°Ｃ０アセトン溶液中の吸光度はλｍａｘ：
６８０ｎｍ、ｆ二４．０７×１０４
以下実施例１〜８と同様の方法で表−１の化合物が！＆
！造できた。Recrystallization from ethyl alcohol gave a 1.68N ma cake of the compound represented by the following formula (6). Melting point 17
The absorbance in 2-174°C0 acetone solution is λmax:
680 nm, f2 4.07 x 104 The compounds in Table 1 were prepared in the same manner as in Examples 1 to 8! &
! I was able to build it.
表
一般式
実施例１オフ
ガラス基板とに実施例２で得られた化合物「のクロロホ
ルム溶液を８０００ｒｐｍＸ２０９ｅＣ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。Table General Formula Example 1 A chloroform solution of the compound obtained in Example 2 was spin-coated on an off-glass substrate under conditions of 8000 rpm x 209 eC to form a recording layer with a thickness of 700 mm, thereby creating an optical information recording medium. .
得られた記録媒体の透過率及び反射率曲線をＩ！５図に
示す。The transmittance and reflectance curves of the obtained recording medium are shown as I! It is shown in Figure 5.
この記録媒体に半導体レーザーを用いスＪット径１μｍ
とし４０ｍＪ／−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。This recording medium uses a semiconductor laser with a diameter of 1 μm.
When irradiation was carried out at 40 mJ/-, the formation of clear spots was observed.
なお真空蒸着法によっても同様な光情報記録媒体が得ら
れた。A similar optical information recording medium was also obtained by vacuum evaporation.
実施例Ｉ Ｊｌ’１
ガラス基板上に実施例６で得られた化合物のクロロホル
ム溶液を８０００ｒｐｍｘ２０８ｅＣ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。Example I Jl'1 A chloroform solution of the compound obtained in Example 6 was spin-coated on a glass substrate under conditions of 8000 rpm x 208 eC to form a recording layer with a thickness of 700 mm, thereby producing an optical information recording medium.
得られた記録媒体の透過率及び反射率曲線を第６図に示
す。The transmittance and reflectance curves of the obtained recording medium are shown in FIG.
この記録媒体に半導体レーザーを用いスーット径１μｍ
とし４０ｍＪ／−で照射を行ったところ明瞭なスぽット
の形成が認められた。This recording medium uses a semiconductor laser with a soot diameter of 1 μm.
When irradiation was carried out at 40 mJ/-, the formation of clear spots was observed.
なお真空蒸着法によっても同様な光情報記録媒体が得ら
れた。A similar optical information recording medium was also obtained by vacuum evaporation.
比較例
ガラス基板とはＡｎｎ、 ５９０ 、９１〜１１０（１
９５４）記載の下記化合物のクロロホルム溶液を８００
０ｒｐｍｘ２Ｑｓｅｃの条件で回転肇布したが、番与←
毎参、塗布直後に結晶化を起こし、均一な薄膜を得るこ
とができなかった。またアセトン溶液中の吸収極大波長
も５１８ｎｍであり、本発明の化合物より短波長側に１
吸収を有し、レーザーの発振波長とのずれが大きく記録
感度の面でも不利であり光情報記録媒体としても有用で
ない。Comparative example glass substrate is Ann, 590, 91-110 (1
954) A chloroform solution of the following compound described in 800
I rotated it under the conditions of 0 rpm x 2 Qsec, but the rotation was ←
In each case, crystallization occurred immediately after coating, making it impossible to obtain a uniform thin film. The absorption maximum wavelength in the acetone solution is also 518 nm, which is 1 on the shorter wavelength side than the compound of the present invention.
It has absorption, has a large deviation from the laser oscillation wavelength, is disadvantageous in terms of recording sensitivity, and is not useful as an optical information recording medium.
媒体の構成を示す断面図である。FIG. 2 is a cross-sectional view showing the configuration of a medium.
１・・・基板、 ２・・・記録層、 ８−−−下引ｈ８、４−−− ｆｆ１ｉｉｌｌｌｌ。1...Substrate, 2...Recording layer, 8---Download h8, 4---ff1iillll.
過率及び反射率スペクトルを示す。第６図は実施例１町
で得られた記録媒体の透過率及び反射率スペクトルを示
す。The transmittance and reflectance spectra are shown. FIG. 6 shows the transmittance and reflectance spectra of the recording medium obtained in Example 1.
（以下余白）(Margin below)
第１図ばないし第４図は本発明の光情報記録第 図 第３図 第２ 図 第４図 第 図 （ｎｍ） 波長 Figures 1 to 4 show the optical information recording system of the present invention. figure Figure 3 Second figure Figure 4 No. figure (nm) wavelength
Claims (3)
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＿２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、置換されていて
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＿１、Ｒ＿２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いてもよい。Ｒ＿３は置
換されていてもよいアルキル基、置換されていてもよい
アルコキシ基、ヒドロキシ基、ハロゲン原子、−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▼、−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▼ ▲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、置換されていてもよい
アルキル基、置換されていてもよいアリール基を表す。 Ｒ＿４は水素原子、置換されていてもよいアルキル基、
置換されていてもよいアルコキシ基、 ヒドロキシ基、ハロゲン原子、−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▼、−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、置換されていてもよいアルキル基、
置換されていてもよいアリール基を表す。Ｒ＿５〜Ｒ＿
７は水素原子またはアルキル基を表す。）で表される化
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. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables etc. ▼, which represents. Here, R_1 and R_2 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or a cyclohexyl group. Further, R_1 and R_2 may form a ring, or may further contain a hetero atom to form a ring. R_3 is an optionally substituted alkyl group, an optionally substituted alkoxy group, a hydroxy group, a halogen atom, -AR
Or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ - A stands for ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -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. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents R, R'
each independently represents a hydrogen atom, an optionally substituted alkyl group, and an optionally substituted aryl group. R_4 is a hydrogen atom, an optionally substituted alkyl group,
an optionally substituted alkoxy group, a hydroxy group, a halogen atom, -AR or ▲numerical formula,
There are chemical formulas, tables, etc. ▼, -A- stands for ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, -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 mathematical formulas, chemical formulas, tables, etc. ▼
represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R and R' each independently represent a hydrogen atom, an optionally substituted alkyl group,
Represents an optionally substituted aryl group. R_5～R_
7 represents a hydrogen atom or an alkyl group. ).
Ｎ＝Ｏ（II） （式中、Ｘは前記と同じ意味を示す。）で表される化合
物とを反応させることを特徴とする請求項１の化合物の
製法。(2) p-nitrobenzyl cyanide and general formula (II)
2. A method for producing a compound according to claim 1, which comprises reacting with a compound represented by N=O(II) (wherein X has the same meaning as above).
特徴とする、光情報記録媒体(3) An optical information recording medium characterized in that the recording layer contains one or more compounds according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63182436A JPH0232164A (en) | 1988-07-20 | 1988-07-20 | Alpha-cyanoazomethine-based compound, production thereof and optical information recording medium using said compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63182436A JPH0232164A (en) | 1988-07-20 | 1988-07-20 | Alpha-cyanoazomethine-based compound, production thereof and optical information recording medium using said compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0232164A true JPH0232164A (en) | 1990-02-01 |
Family
ID=16118236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63182436A Pending JPH0232164A (en) | 1988-07-20 | 1988-07-20 | Alpha-cyanoazomethine-based compound, production thereof and optical information recording medium using said compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0232164A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5256624A (en) * | 1991-04-18 | 1993-10-26 | Basf Aktiengesellschaft | Transfer of methine dyes |
| EP0691213A1 (en) * | 1994-07-04 | 1996-01-10 | Agfa-Gevaert N.V. | Dye donor element for use in thermal transfer printing |
-
1988
- 1988-07-20 JP JP63182436A patent/JPH0232164A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5256624A (en) * | 1991-04-18 | 1993-10-26 | Basf Aktiengesellschaft | Transfer of methine dyes |
| EP0691213A1 (en) * | 1994-07-04 | 1996-01-10 | Agfa-Gevaert N.V. | Dye donor element for use in thermal transfer printing |
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