JPS63200332A - Dioxadinaphtopentacene derivative and optical recording medium using said derivative - Google Patents
Dioxadinaphtopentacene derivative and optical recording medium using said derivativeInfo
- Publication number
- JPS63200332A JPS63200332A JP62032883A JP3288387A JPS63200332A JP S63200332 A JPS63200332 A JP S63200332A JP 62032883 A JP62032883 A JP 62032883A JP 3288387 A JP3288387 A JP 3288387A JP S63200332 A JPS63200332 A JP S63200332A
- Authority
- JP
- Japan
- Prior art keywords
- optical recording
- recording medium
- formula
- group
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 25
- 239000000758 substrate Substances 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000002964 pentacenes Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- 125000004970 halomethyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 7
- 238000000576 coating method Methods 0.000 abstract description 12
- 239000011248 coating agent Substances 0.000 abstract description 11
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000007740 vapor deposition Methods 0.000 abstract description 3
- 238000002310 reflectometry Methods 0.000 abstract 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- -1 methoxyethoxy group Chemical group 0.000 description 6
- 239000010409 thin film Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- 239000011011 black crystal Substances 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000007606 doctor blade method Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- ORIHZIZPTZTNCU-VMPITWQZSA-N 2-[(E)-hydroxyiminomethyl]phenol Chemical compound O\N=C\C1=CC=CC=C1O ORIHZIZPTZTNCU-VMPITWQZSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、９．１９−ジオキサジナフトー［３，２，１
−ｄａ；３，２．１−ＯＰココペンタセン誘導体及び該
誘導体を使用した光学記録媒体に関するものである。詳
しくは、本発明は、新規ジオキサジナフトペンタセン系
誘導体及び該誘導体を利用してなる、半導体レーザーの
発振波長の光エネルギーにより物質状態の変化を利用し
て記録を行なう光学記録媒体に関するものである。Detailed Description of the Invention [Industrial Application Field] The present invention provides 9,19-dioxazinaphthol [3,2,1
-da;3,2.1-OP Cocopentacene derivative and an optical recording medium using the derivative. Specifically, the present invention relates to a novel dioxazinaphthopentacene derivative and an optical recording medium that uses the derivative and performs recording by utilizing a change in the state of matter due to optical energy at the oscillation wavelength of a semiconductor laser. be.
［従来の技術］
半導体レーザーの発振波長の光エネルギーにより物質状
態の変化を利用して記録を行なう光学記録媒体としては
、従来より種々の構成のものが知られている。[Prior Art] Various configurations are conventionally known as optical recording media that perform recording by utilizing changes in the state of matter due to optical energy at the oscillation wavelength of a semiconductor laser.
例えば、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。また、特開昭５８−８３３４４号公報にはフェナ
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。For example, JP-A-55-97033 discloses a method in which a single layer of a phthalocyanine dye is provided on a substrate. Further, JP-A-58-83344 discloses a recording layer in which a phenalene dye is provided, and JP-A-58-224793 discloses a recording layer in which a naphthoquinone dye is provided.
［発明が解決しようとする問題点］
上記従来の光学記録媒体のうち、特開昭５５−９７０３
３号に開示されるフタロシアニン軍色来を用いたもので
は、フタロシアニン系色素は感度が低い、分解点が高く
蒸着しにくい等の問題点を有し、更に有機溶媒に対する
溶解性が著しく低く、塗布によるコーティングに使用す
ることができないという問題点も有している。[Problems to be solved by the invention] Among the conventional optical recording media mentioned above, Japanese Patent Application Laid-Open No. 55-9703
The phthalocyanine pigment disclosed in No. 3 has problems such as low sensitivity, high decomposition point and difficulty in vapor deposition, and also has extremely low solubility in organic solvents, making coating difficult. Another problem is that it cannot be used for coating with.
一方、特開昭５８−８３３４４号、同５８−２２４７９
３号に開示される色素は、蒸着しやすいという利点の反
面、反射率が低いという問題点を有している。反射率が
低いとレーザー光により記録された部分と未記録部分と
の反射率に関係するコントラストが低くなり、記録され
た情報の再生が困難となる。また、一般に有機系色素は
保存安定性が劣るという問題点を有している。On the other hand, JP-A-58-83344 and JP-A-58-22479
The dye disclosed in No. 3 has the advantage of being easy to vapor deposit, but has the problem of low reflectance. If the reflectance is low, the contrast related to the reflectance between the portion recorded by the laser beam and the unrecorded portion will be low, making it difficult to reproduce the recorded information. Additionally, organic dyes generally have a problem of poor storage stability.
［問題点を解決するための手段］
本発明は、上記従来の問題点を解決し、蒸着が容易で、
有機溶媒に対する溶解性が高く、塗布によるコーティン
グも可能で、しかも、反射率が高く、コントラストが良
好で保存性に優れている、新規なジオキサジナフトベン
タセン系話導体及びそれを用いた光学記録媒体を提供す
ることを目的ヒするものでありて、
下記色素骨格
ＮＣＣＮ
入
ＣＮ
（式中、ＸはＣく 又は０を示す。）ＣＮ
で表わされる９、１９−ジオキサジナフトー［３，２，
１−ｄａ ；３，２．１−ＯＰ］ペンタセン系誘導体、
及び、上記誘導体を含む記録層を設けたことを特徴とす
る光学記録媒体、を要旨とするものである。[Means for Solving the Problems] The present invention solves the above-mentioned conventional problems, and provides easy vapor deposition.
A novel dioxazinaphthobentacene conductor that has high solubility in organic solvents, can be coated by coating, has high reflectance, good contrast, and has excellent storage stability, and optical conductors using the same. The purpose is to provide a recording medium containing 9,19-dioxazinaphtho[3, 2,
1-da; 3,2.1-OP] pentacene derivative,
And an optical recording medium characterized by being provided with a recording layer containing the above-mentioned derivative.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明において、９．１９−ジオキサジナフト−［３，
２，１−ｄｅ；３，２．１−ＯＰＩペンタセン系誘導体
としては、好ましくは、下記一般。In the present invention, 9,19-dioxazinaphtho-[3,
As the 2,1-de;3,2.1-OPI pentacene derivative, the following compounds are preferred.
式［！］ 入 ＣＮ （式中、ＸはＣく 又は０を示し、Ｒ’、Ｒ”。formula[! ] Enter C.N. (In the formula, X represents C or 0, R', R''.
ＣＮ
Ｒ３，Ｒ４は水素原子、アルキル基、アルコキシ基、ア
ルコキシアルコキシ基、ハロメチル基又はハロゲン原子
を示し、ａｌｌ、 ＦＬ６は水素原子又はハロゲン原
子を示す、）
で表わされる色素が挙げられる。CN R3 and R4 represent a hydrogen atom, an alkyl group, an alkoxy group, an alkoxyalkoxy group, a halomethyl group, or a halogen atom, and all and FL6 represent a hydrogen atom or a halogen atom.
上記一般式［Ｉ］で表わされる色素において、Ｒ’、
Ｒ”、 Ｒ’、 Ｒ’で示されるアルキル基とし
ては、メチル基、エチル基、直鎖状又は分岐状のプロピ
ノσ基、ブチル基、ペンチル基、ヘプチル基、ヘキシル
基、オクチル基等のＣ１〜。のアルキル基が挙げられる
。アルコキシ基としては、メトキシ基、エトキシ基、直
鎖状又は分岐状のプロポキシ基、ブトキシ基、ペンチル
オキシ基、ヘプチルオキシ基、ヘキシルオキシ基、オク
チルオキシ基等の０１〜６のアルコキシ基が挙げられる
。また、アルコキシアルコキシ基としては、メトキシエ
トキシ基、エトキシエトキシ基、メトキシプロポキシ基
、ブトキシエトキシ基等が挙げられ、ハロメチル基とし
ては、クロロメチル基、ブロモメチル基等が挙げられる
。ハロゲン原子としては、フッ素原子、臭素原子、塩素
原子、ヨウ素原子が挙げられる。In the dye represented by the above general formula [I], R',
Examples of the alkyl group represented by R'', R', and R' include C1 groups such as methyl group, ethyl group, linear or branched propino σ group, butyl group, pentyl group, heptyl group, hexyl group, and octyl group. Examples of alkyl groups include methoxy groups, ethoxy groups, linear or branched propoxy groups, butoxy groups, pentyloxy groups, heptyloxy groups, hexyloxy groups, octyloxy groups, etc. Examples of the alkoxy alkoxy group include a methoxyethoxy group, an ethoxyethoxy group, a methoxypropoxy group, a butoxyethoxy group, and examples of the halomethyl group include a chloromethyl group and a bromomethyl group. Examples of the halogen atom include a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom.
また、ａｌｌ、Ｒ８で示されるハロゲン原子としては、
フッ素原子、臭素原子、塩素原子、ヨウ素原子が挙げら
れる。In addition, the halogen atoms represented by all and R8 are:
Examples include fluorine atom, bromine atom, chlorine atom, and iodine atom.
前記一般式［Ｉ］で示される色素は、一般に７００〜９
００ｎｍの波長帯域で吸収を有し、しる。The dye represented by the general formula [I] generally has a molecular weight of 700 to 9
It has absorption in the wavelength band of 00 nm.
前記一般式［Ｉ］で示されるジオキサジナフトペンタセ
ン系化合物は〜、例えば、下記一般式［１１］
（式中、Ｒ’、Ｒ２，Ｒ’、Ｒ’、Ｒ’、Ｒ’！＊前記
定義に同じ、）
で表わされる化合物に、クロロホルム中、ピリジン、四
塩化チタンの存在下、下記構造式０式％
で表わされるマロンニトリルを反応させることによって
製造することができる。The dioxazinaphtopentacene compound represented by the general formula [I] is, for example, the following general formula [11] (wherein R', R2, R', R', R', R'! *The above It can be produced by reacting a compound represented by (same as the definition) with malonitrile represented by the following structural formula % in the presence of pyridine and titanium tetrachloride in chloroform.
次に、このような本発明の新規ジオキサジナフトベンタ
セン系化合物を用いた、本発明の光学記録媒体について
説明する。Next, an optical recording medium of the present invention using such a novel dioxazinaphthobentacene compound of the present invention will be explained.
本発明の光学記録媒体は、基本的には基板と記録層とか
ら構成されるものであるが、更に必要に応じて基板上に
下引き層を、あるいは、記録層上に保護層を設けること
ができる。The optical recording medium of the present invention basically consists of a substrate and a recording layer, but if necessary, an undercoat layer may be provided on the substrate or a protective layer may be provided on the recording layer. Can be done.
本発明で用いる基板は、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も良い。基板材料の材質として
は、ガラス、プラスチック、紙、板状又は箔状の金属等
の、一般的な記録材料の支持体が挙げられるが、これら
のうち、プラスチックが種々の点から好適である。プラ
スチックとしては、アクリル樹脂、メタアクリル樹脂、
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、ポリサルホン樹脂等が挙げ
られる。The substrate used in the present invention may be transparent or opaque to the laser beam used. Examples of the substrate material include supports for general recording materials such as glass, plastic, paper, plate-shaped or foil-shaped metal, and among these, plastic is preferred from various points of view. Plastics include acrylic resin, methacrylic resin,
Vinyl acetate resin, vinyl chloride resin, nitrocellulose,
Examples include polyethylene resin, polypropylene resin, polycarbonate resin, polyimide resin, polysulfone resin, and the like.
本発明の光学記録媒体における情報記録層として、前記
一般式［Ｉ］の化合物を使用する際、膜厚は１００人〜
５μｍ１好ましくは１０００人〜３μｍとするのが好適
である。When the compound of general formula [I] is used as the information recording layer in the optical recording medium of the present invention, the film thickness is 100 to
It is suitable to set it as 5 micrometers 1, preferably 1000 people - 3 micrometers.
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、キャスト法、スピナー法、浸漬法など
一般に行なわれている薄膜形成法を採用することができ
る。As a film forming method, commonly used thin film forming methods such as a vacuum evaporation method, a sputtering method, a doctor blade method, a casting method, a spinner method, and a dipping method can be employed.
成膜に際しては、必要に応じてバインダーを使用するこ
ともできる。バインダーとしてはＰＶＡ、ＰＶＰ、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既知のものが用いられ、これら
のバインダー樹脂に対する前記一般式［Ｉ］の化合物の
量は重量比で０．０１以上であることが望ましい。When forming a film, a binder can also be used as necessary. Known binders such as PVA, PVP, nitrocellulose, cellulose acetate, polyvinyl butyral, and polycarbonate are used, and the weight ratio of the compound of the general formula [I] to these binder resins is 0.01 or more. This is desirable.
また、記録体の安定性や耐光性向上のために、−重項酸
素クエンチャーとして遷穆金属キレート化合物（例えば
、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−α−
ジケトン等）を含有させても良い。更に、必要に応じて
他の色素を併用することもできる。他の色素としては、
別の種類の同系統の化合物でも良いし、トリアリールメ
タン系色素、アゾ染料、シアニン系色素、スクワリリウ
ム系色素など他系統の色素でも良い。Additionally, in order to improve the stability and light resistance of the recording medium, transitional metal chelate compounds (e.g., acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-α-
diketone, etc.) may be included. Furthermore, other dyes can be used in combination if necessary. Other dyes include
It may be a different type of compound of the same type, or it may be a dye of another type, such as a triarylmethane dye, an azo dye, a cyanine dye, or a squarylium dye.
ドクターブレード法、キャスト法、スピナー法、浸漬法
、特に、スピナー法等の塗布方法により記録層を形成す
る場合の塗布溶媒としては、ブロモホルム、ジブロモエ
タン、テトラクロロエタン、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１２０
〜１８０℃のものが好適に使用される。When forming a recording layer by a coating method such as a doctor blade method, a casting method, a spinner method, or a dipping method, especially a spinner method, coating solvents include bromoform, dibromoethane, tetrachloroethane, ethyl cellosolve, xylene, chlorobenzene, and cyclohexanone. etc. boiling point 120
~180°C is preferably used.
なお、スピナー法による成膜の場合、回転数は５００〜
５０００ｒｐｍが好ましく、スピンコードの後、場合に
よっては、加熱あるいは溶媒蒸気にあてる等の処理を行
なっても良い。In addition, in the case of film formation by the spinner method, the rotation speed is 500~
The speed is preferably 5000 rpm, and after the spin code, treatment such as heating or exposure to solvent vapor may be performed as the case requires.
本発明の光学記録媒体の記録層は基板の両面に設けても
良いし、片面だけに設けても良い。The recording layer of the optical recording medium of the present invention may be provided on both sides of the substrate or only on one side.
上記の様にして得られた記録体への記録は、通常、基体
の両面又は片面に設けた記録層に、１μｍ程度に集束し
たレーザー光、好ましくは、平４胃１士１７−４Ｆ−ハ
嘉ル凱イス京１．彎上ｈり４外らレーザー光の照射され
た部分には、レーザー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る。Recording on the recording medium obtained as described above is usually performed using a laser beam focused to about 1 μm, preferably on the recording layer provided on both sides or one side of the substrate. Kalu Kai Isukyo 1. The area irradiated with the laser beam from the outside of the curve will undergo decomposition and decomposition due to the absorption of laser energy.
Thermal deformation of the recording layer, such as evaporation and melting, occurs.
記録された情報の再生は、レーザー光により、熱的変形
が起きている部分と起きていない部分の反射率の差を読
み取る事により行なう。The recorded information is reproduced by using laser light to read the difference in reflectance between areas where thermal deformation has occurred and areas where thermal deformation has not occurred.
本発明の光学記録媒体へ、の記録又は再生に使用される
レーザー光は軽量性、取扱いの容易さ、コンパクト性な
どの点から半導体レーザーが好適である。As the laser beam used for recording or reproducing information on the optical recording medium of the present invention, a semiconductor laser is preferable from the viewpoints of light weight, ease of handling, and compactness.
［作 用］
本発明で提供される９、１９−ジオキサジナフト−［３
，２，１−ｄｅ；３．２．１−ＯＰ］ペンタセン系誘導
体は、蒸着が容易で、有機溶媒に対する溶解性が高く、
塗布によるコーティングも可能で、しかも、反射率が高
く、コントラストが良好で保存性に優れている。[Function] 9,19-dioxazinaphtho-[3
,2,1-de;3.2.1-OP] Pentacene derivatives are easy to vapor deposit, have high solubility in organic solvents,
It can also be coated by painting, and it has high reflectance, good contrast, and excellent storage stability.
従って、このような誘導体を用いることにより、容易か
つ効率的に記録、再生等の諸特性に優れしかも安定性の
高い高特性光学記録媒体を得ることができる。Therefore, by using such a derivative, it is possible to easily and efficiently obtain a high-performance optical recording medium that is excellent in recording and reproducing properties and is highly stable.
［実施例］
以下、実施例を挙げて本発明をより具体的に説明するが
、本発明は、その要旨を越えない限り、以下の実施例に
限定されるものではない。[Examples] Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples unless the gist thereof is exceeded.
実施例１
炙−１
下記構造式
で表わされる化合物１２．２ｇをクロロホルム１２５ｍ
ｆに溶解させ、四塩化チタン６．９ｍＩＬを加えた。次
いで、これに下記構造式
０式％
で表わされるマロンニトリル１６．５ｇとピリジン４０
．５ｍｊ２及びクロロホルム１２５ｍλとからなる溶液
を滴下した。Example 1 Roasted-1 12.2g of the compound represented by the following structural formula was added to 125ml of chloroform.
6.9 mL of titanium tetrachloride was added. Next, 16.5 g of malonitrile represented by the following structural formula 0% and 40 g of pyridine were added to this.
．． A solution consisting of 5 mj2 and 125 mλ of chloroform was added dropwise.
滴下後、５時間加熱還流した後、室温まで放冷し、反応
生成物を水５００ｍｕ中へ注いだ、析出結晶をン濾過し
、水洗後、メタノール懸濁を２回繰り返し、黒色結晶１
０ｇを得た。この黒色結晶をシリカゲルカラムクロマト
グラフィーで精製して１、下記物性を有し、下記構造式
［ＩＩＩ ］で表わされる黒色結晶を得た。After dropping, the reaction product was heated under reflux for 5 hours, cooled to room temperature, and the reaction product was poured into 500 mu of water.The precipitated crystals were filtered, washed with water, and suspended in methanol twice.
Obtained 0g. This black crystal was purified by silica gel column chromatography to obtain a black crystal having the following physical properties and represented by the following structural formula [III].
分子吸光係数（ε）：ａ、ｏｘｔｏ’
クロロホルム溶液中のλｗａｘニア９０ｎｍマススペク
トル： ６４８ （Ｍ” ）融点：２７０〜２７５℃
處−１
上記構造式［ＩＩＩ ］で表わされる色素１．０ｇをテ
トラクロロエタン５０ｇに溶解し、０．２２μｍのフィ
ルターで炉通し、溶解液を得た。この溶液２ｍｊ２を、
深さ７００人、巾０．７μｍの紫外線硬化樹脂による溝
（グループ）つきＰＭＭＡ樹脂基板（１２０ｍｍφ）上
に滴下し、スピナー法により１１０００ｒｐの回転数で
塗布した。塗布後、６０℃で１０分間乾燥した。同一条
件でガラス板に塗布して、タリステップによる膜厚測定
したところ、７５０人であった。塗布膜の最大吸収波長
は７６０ｎｍであり、反射率は２４％（８３０ｎｍ）で
あった、スペクトルの形状は巾広かった。第１図に塗布
膜の吸収及び反射のスペクトルを示す。Molecular extinction coefficient (ε): a, oxto' λwax near 90 nm mass spectrum in chloroform solution: 648 (M'') Melting point: 270-275°C Room-1 1.0 g of the dye represented by the above structural formula [III] was added to tetra Dissolved in 50 g of chloroethane and passed through a furnace through a 0.22 μm filter to obtain a solution. 2 mj2 of this solution was
It was dropped onto a PMMA resin substrate (120 mmφ) with grooves (groups) made of ultraviolet curable resin having a depth of 700 mm and a width of 0.7 μm, and was applied by a spinner method at a rotation speed of 11,000 rpm. After coating, it was dried at 60°C for 10 minutes. When the film was coated on a glass plate under the same conditions and the film thickness was measured using Talystep, it was found to be 750 people. The maximum absorption wavelength of the coating film was 760 nm, the reflectance was 24% (830 nm), and the shape of the spectrum was wide. FIG. 1 shows the absorption and reflection spectra of the coating film.
光」ζ録
この塗布膜に、中心波長８３０ｎｍの半導体レーザー光
を出力４ｍＷでビーム径１μｍで照射した所、巾約１μ
ｍ１ビツト長約２μｍの輪郭の極めて明瞭なビットが形
成された。動特性評価でＣ／Ｎ比は５８ｄＢ （８ｒｎ
Ｗ）で高く、保存安定性（６０℃、８０％ＲＨ）も良好
でありた。When this coating film was irradiated with semiconductor laser light with a center wavelength of 830 nm and a beam diameter of 1 μm at an output of 4 mW, the width was approximately 1 μm.
A very well-defined bit with a m1 bit length of about 2 μm was formed. In the dynamic characteristic evaluation, the C/N ratio was 58dB (8rn
W), and the storage stability (60° C., 80% RH) was also good.
実施例２
実施例１において、前記構造式［ＩＩＩ ］で表わされ
る化合物の代わりに、下記第１表に示す化合物を使用し
たこと以外は同様にして、成膜を行なったところ、第１
表に示す最大吸収波長をもつ薄膜基板が得られた。Example 2 A film was formed in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of the compound represented by the structural formula [III].
A thin film substrate having the maximum absorption wavelength shown in the table was obtained.
このようにして得られた薄膜に、光源として半導体レー
ザーを用いて書き込みを行なったところ、均一かつ明瞭
な形状のビットが得られ、そのＣ／Ｎ比も良好であり、
保存性も良好であった。When writing was performed on the thin film thus obtained using a semiconductor laser as a light source, bits with a uniform and clear shape were obtained, and the C/N ratio was also good.
Preservability was also good.
実施例３
下記構造式［ＩＶ ］で表わされる色素（分子吸光係数
（ε）及びクロロホルム溶液中のλ、□は下記に記す、
）を１．６ｘ １０−’ Ｔｏｒｒの真空下で、約８０
〜１５０℃に加熱し、板厚１．２ｍｍの１．６μｍピッ
チの溝（グループ）つきポリカーボネート樹脂（以下、
ＰＣと記す）基板上に真空蒸着した。蒸着膜厚を水晶振
動式膜厚計による真空蒸着膜厚測定で測定した結果、６
００人であった。また、分光光度計による最大吸収波長
は７６０ｎｍであり、反射率は２８％（８３０ｎａ＋）
であった、スペクトルの形状は、巾広かった。Example 3 A dye represented by the following structural formula [IV] (molecular extinction coefficient (ε) and λ in chloroform solution, □ are shown below,
) under a vacuum of 1.6 x 10-' Torr, approximately 80
Heating to ~150°C, polycarbonate resin (hereinafter referred to as
(denoted as PC) was vacuum evaporated onto a substrate. The thickness of the deposited film was measured using a quartz crystal film thickness meter, and the result was 6.
There were 00 people. Additionally, the maximum absorption wavelength measured by a spectrophotometer is 760 nm, and the reflectance is 28% (830 na+).
The shape of the spectrum was broad.
分子吸光係数（ε）：８．０ＸＩＯ’
クロロホルム溶液中のλ□ｘ ニア７８ｎｍこのように
して得られた薄膜に、光源として、中心波長８３０ｎｍ
の半導体レーザーを用い、ビーム径約１μｍで書き込み
を行なったところ、均一かつ明瞭な形状のビットが得ら
れ、動特性評価ではＣ／Ｎ比は５５ｄＢ （８ｍＷ）で
良好であった。Molecular extinction coefficient (ε): 8.0
When writing was performed using a semiconductor laser with a beam diameter of about 1 μm, bits with a uniform and clear shape were obtained, and the C/N ratio was good at 55 dB (8 mW) in dynamic characteristic evaluation.
また、この記録媒体は、室内光中、温度６０℃、湿度９
０％の条件下で良好な保存性を示した。Furthermore, this recording medium was used in indoor light at a temperature of 60°C and a humidity of 9.
It showed good storage stability under 0% condition.
実施例４
実施例１において用いた色素の代わりに、下記第２表に
示した化合物を使用して蒸着したところ、下記第２表に
示す最大吸収波長をもつ薄膜基板を得た。Example 4 Instead of the dye used in Example 1, the compounds shown in Table 2 below were used and deposited, and thin film substrates having the maximum absorption wavelengths shown in Table 2 below were obtained.
得られた薄膜に、光源として半導体レーザーを用いて書
き込みを行なったところ均一かつ明瞭な形状のビットが
得られた。Ｃ／Ｎ比も良好であり、保存性も良好であっ
た。When writing was performed on the obtained thin film using a semiconductor laser as a light source, bits with a uniform and clear shape were obtained. The C/N ratio was also good, and the storage stability was also good.
第２表
［発明の効果］
以上詳述した通り、本発明のジオキサジナフトベンタセ
ン系話導体は、蒸着が容易で、有機溶媒に対する溶解性
が高く、塗布によるコーティングも可能で、しかも、反
射率が高く、コントラストが良好で保存性に優れている
。Table 2 [Effects of the Invention] As detailed above, the dioxazinaphthobentacene conductor of the present invention is easy to vapor deposit, has high solubility in organic solvents, can be coated by coating, and High reflectance, good contrast, and excellent storage stability.
従って、このような誘導体を含む記録層を設けた本発明
の光学記録媒体は、容易かつ効率的に製造することがで
き、その記録、再生等の緒特性にも優れしかも安定性が
高いため、工業的に極めて有用である。Therefore, the optical recording medium of the present invention provided with a recording layer containing such a derivative can be manufactured easily and efficiently, has excellent recording and reproduction characteristics, and is highly stable. It is extremely useful industrially.
第１図は実施例１で得られた塗布膜の吸収及び反射スペ
クトル線図である。FIG. 1 is an absorption and reflection spectrum diagram of the coating film obtained in Example 1.
Claims (4)
を示す。） で表わされる９、１９−ジオキサジナフト−［３、２、
１−ｄｅ；３、２、１−ＯＰ］ペンタセン系誘導体。(1) The following pigment skeleton ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or O
shows. ) 9,19-dioxadinaphtho-[3,2,
1-de;3,2,1-OP]pentacene derivative.
を示し、Ｒ＾１、Ｒ＾２、Ｒ＾３、Ｒ＾４は水素原子、
アルキル基、アルコキシ基、アルコキシアルコキシ基、
ハロメチル基又はハロゲン原子を示し、Ｒ＾５、Ｒ＾６
は水素原子又はハロゲン原子を示す。） で表わされることを特徴とする特許請求の範囲第１項に
記載の９、１９−ジオキサジナフト−［３、２、１−ｄ
ｅ；３、２、１−ＯＰ］ペンタセン系誘導体。(2) The following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or O
, R^1, R^2, R^3, R^4 are hydrogen atoms,
Alkyl group, alkoxy group, alkoxyalkoxy group,
Indicates a halomethyl group or halogen atom, R^5, R^6
represents a hydrogen atom or a halogen atom. ) 9,19-dioxazinaphtho-[3,2,1-d
e; 3,2,1-OP] pentacene derivative.
によって記録再生を行なうための光学記録媒体であって
、基板に下記色素骨格 ▲数式、化学式、表等があります▼ （式中、Ｘは▲数式、化学式、表等があります▼又はＯ
を示す。） で表わされる９、１９−ジオキサジナフト−［３、２、
１−ｄｅ；３、２、１−ＯＰ］ペンタセン系誘導体を含
む記録層を設けたことを特徴とする光学記録媒体。(3) It is an optical recording medium for recording and reproducing by causing a state change with a laser beam, and the substrate has the following pigment skeleton ▲ mathematical formula, chemical formula, table, etc. ▼ (wherein, X is ▲ mathematical formula, chemical formula There are tables, etc. ▼ or O
shows. ) 9,19-dioxadinaphtho-[3,2,
1-de;3,2,1-OP] An optical recording medium comprising a recording layer containing a pentacene derivative.
ｅ；３、２、１−ＯＰ］ペンタセン系誘導体が、下記一
般式 ▲数式、化学式、表等があります▼ （式中、ＸはＣ又はＯを示し、Ｒ＾１、Ｒ＾２、Ｒ＾３
、Ｒ＾４は水素原子、アルキル基、アルコキシ基、アル
コキシアルコキシ基、ハロメチル基又はハロゲン原子を
示し、Ｒ＾５、Ｒ＾６は水素原子又はハロゲン原子を示
す。） で表わされるものであることを特徴とする特許請求の範
囲第３項に記載の光学記録媒体。(4) 9,19-dioxazinaphtho-[3,2,1-d
e; 3, 2, 1-OP] Pentacene derivatives have the following general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, X represents C or O, R^1, R^2, R^ 3
, R^4 represents a hydrogen atom, an alkyl group, an alkoxy group, an alkoxyalkoxy group, a halomethyl group, or a halogen atom, and R^5 and R^6 represent a hydrogen atom or a halogen atom. ) The optical recording medium according to claim 3, characterized in that the optical recording medium is represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62032883A JPH0713192B2 (en) | 1987-02-16 | 1987-02-16 | Dioxadinaphthopentacene derivative and optical recording medium using the derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62032883A JPH0713192B2 (en) | 1987-02-16 | 1987-02-16 | Dioxadinaphthopentacene derivative and optical recording medium using the derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63200332A true JPS63200332A (en) | 1988-08-18 |
| JPH0713192B2 JPH0713192B2 (en) | 1995-02-15 |
Family
ID=12371270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62032883A Expired - Fee Related JPH0713192B2 (en) | 1987-02-16 | 1987-02-16 | Dioxadinaphthopentacene derivative and optical recording medium using the derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0713192B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007291245A (en) * | 2006-04-25 | 2007-11-08 | Mitsubishi Chemicals Corp | Laser absorbent for laser welding, resin composition for laser welding, molded article, and method for manufacturing molded article |
-
1987
- 1987-02-16 JP JP62032883A patent/JPH0713192B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007291245A (en) * | 2006-04-25 | 2007-11-08 | Mitsubishi Chemicals Corp | Laser absorbent for laser welding, resin composition for laser welding, molded article, and method for manufacturing molded article |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0713192B2 (en) | 1995-02-15 |
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