JPH0376685A - Optical recording medium - Google Patents
Optical recording mediumInfo
- Publication number
- JPH0376685A JPH0376685A JP1212455A JP21245589A JPH0376685A JP H0376685 A JPH0376685 A JP H0376685A JP 1212455 A JP1212455 A JP 1212455A JP 21245589 A JP21245589 A JP 21245589A JP H0376685 A JPH0376685 A JP H0376685A
- Authority
- JP
- Japan
- Prior art keywords
- recording layer
- recording medium
- optical recording
- alkyl group
- lower alkyl
- 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
- 230000003287 optical effect Effects 0.000 title claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 150000001450 anions Chemical class 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- -1 azulene compound Chemical class 0.000 claims description 22
- CUFNKYGDVFVPHO-UHFFFAOYSA-N Azulene Natural products C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 abstract description 16
- 239000011248 coating agent Substances 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 238000007740 vapor deposition Methods 0.000 abstract description 5
- 230000001678 irradiating effect Effects 0.000 abstract description 3
- 239000012528 membrane Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000010410 layer Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 14
- 239000000975 dye Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- BNDRWEVUODOUDW-UHFFFAOYSA-N 3-Hydroxy-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)O BNDRWEVUODOUDW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000007606 doctor blade method Methods 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001007 phthalocyanine dye Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- 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
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- NBEGXSQMVJTIAR-UHFFFAOYSA-N 1-hydroxy-3-methylbutan-2-one Chemical compound CC(C)C(=O)CO NBEGXSQMVJTIAR-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
- DWZBSOVYCROKJR-UHFFFAOYSA-N 4-(2-methylphenyl)butan-1-ol Chemical compound CC1=CC=CC=C1CCCCO DWZBSOVYCROKJR-UHFFFAOYSA-N 0.000 description 1
- LDZLXQFDGRCELX-UHFFFAOYSA-N 4-phenylbutan-1-ol Chemical compound OCCCCC1=CC=CC=C1 LDZLXQFDGRCELX-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910004713 HPF6 Inorganic materials 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910004074 SiF6 Inorganic materials 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
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 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
- 239000000049 pigment Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide 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
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 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
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Thermal Transfer Or Thermal Recording In General (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、光学記録媒体に係り、詳しくは記録層に特定
のアズレン系化合物を含有する光学記録媒体に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an optical recording medium, and more particularly to an optical recording medium containing a specific azulene compound in its recording layer.
レーザーを用いた光学記録は、高密度の情報記録保存お
よび再生を可能とするため、近年、特にその開発がとり
すすめられている。Optical recording using lasers has been particularly developed in recent years because it enables high-density information recording storage and reproduction.
光学記録媒体の−゛例としては、光ディスクを挙げるこ
とができる。一般に、光ディスクは、円形の基体に設け
られた薄い記録層に、１μｍ程度に集束したレーザー光
を照射し、高密度の情報記録を行なうものである。その
記録は、照射されたレーザー光エネルギーの吸収によっ
て、その個所の記録層に、分解、蒸発、溶解等の熱的変
形が生成することにより行なわれる。また、記録された
情報の再生は、レーザー光により変形が起きている部分
と起きていない部分の反射率の差を読み取ることにより
行なわれる。An example of an optical recording medium is an optical disc. In general, optical discs record high-density information by irradiating a thin recording layer provided on a circular base with laser light focused to about 1 μm. The recording is performed by thermal deformation such as decomposition, evaporation, melting, etc. occurring in the recording layer at that location due to absorption of irradiated laser light energy. Further, recorded information is reproduced by reading the difference in reflectance between a portion where deformation has occurred and a portion where no deformation has occurred by laser light.
したがって、光学記録媒体は、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
の再生を正確に行なうため、再生に使用する特定波長の
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 to laser light of a specific wavelength.
この種の光学的記録媒体としては、種々の構成のものが
知られている。Various configurations of this type of optical recording medium are known.
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。しかしながらフタロシアニン系色素は感度が低く
、また分解点が高く蒸着しにくい等の問題点を有し、さ
ら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。For example, JP-A-55-97033 discloses a method in which a single layer of a phthalocyanine dye is provided on a substrate. However, phthalocyanine dyes have problems such as low sensitivity, high decomposition point, and difficulty in vapor deposition.Furthermore, they have extremely low solubility in organic solvents, making them unsuitable for use in coatings. ing.
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。し
かし、このような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は低くなり、記録された
情報の再生が困難となる。更に、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。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. However, although such dyes have the advantage of being easy to deposit, they have 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. Furthermore, organic dyes generally have a problem of poor storage stability.
本発明は、塗布または蒸着による薄膜形成が可能であり
光記録用として有用なアズレン系化合物を記録層に含有
する光学記録媒体を提供することを目的とするものであ
る。An object of the present invention is to provide an optical recording medium containing an azulene compound in a recording layer that can be formed into a thin film by coating or vapor deposition and is useful for optical recording.
本発明者らは、鋭意検討した結果、下記一般式（１）で
示されるアズレン系化合物が、レーザー光線により状態
変化を生せしめることによって記録再生を行なうための
光学記録媒体の色素として優れた特性を有することを見
出し、本発明に到達した。As a result of intensive studies, the present inventors have found that the azulene compound represented by the following general formula (1) has excellent properties as a pigment for optical recording media for recording and reproducing by causing a state change with a laser beam. The present invention was achieved based on the discovery that the present invention has the following properties.
即ち、本発明の要旨は、光照射によりその光学的性質を
変化させて情報を記録する記録層を有する光学記録媒体
において、該記録層が一般式（Ｉ］まず、本発明の光学
記録媒体の記録層に含有されるアズレン系化合物につい
て説明する。That is, the gist of the present invention is to provide an optical recording medium having a recording layer that records information by changing its optical properties by irradiation with light, in which the recording layer has the general formula (I). The azulene compound contained in the recording layer will be explained.
本発明に係るアズレン系化合物は下記一般式（Ｉ）で示
されることを特徴とする。The azulene compound according to the present invention is characterized by being represented by the following general formula (I).
（Ｘ３）。(X3).
（式中、Ｒ＋、ＲＺ及びＲ３は水素原子、低級アルキル
基又は低級アルコキシカルボニル基を表わし、Ｘｌ、Ｘ
ｌ及びＸ３は低級アルキル基又はハロゲン原子を表わし
、ｌ、ｍ及びｎはＯ〜５の整数を表わす。Ｚｌは陰イオ
ンを表わし、ｐは１又は２を表わす。）
で示されるアズレン系化合物を含有することを特徴とす
る光学記録媒体に存する。(In the formula, R+, RZ and R3 represent a hydrogen atom, a lower alkyl group or a lower alkoxycarbonyl group,
1 and X3 represent a lower alkyl group or a halogen atom, and 1, m and n represent an integer of O to 5. Zl represents an anion, and p represents 1 or 2. ) An optical recording medium characterized by containing an azulene compound represented by the following.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
（Ｘ３）。(X3).
（式中、Ｒ１，Ｒ２及びＲ″は水素原子、低級アルキル
基又は低級アルコキシカルボニル基を表わし、ＸＩ、Ｘ
ｌ及びＸ３は低級アルキル基又はハロゲン原子を表わし
、１２． ｍ及びｎは０〜５の整数を表わす ｚｐ−は
陰イオンを表わし、ｐは１又は２を表わｔｏ ＞
一般式（Ｉ）中、Ｒ１，Ｒ２及びＲ３で表わされる低級
アルキル基としては、メチル基、エチル基、プロピル基
、ブチル基、ペンチル基、ヘキシル基等の炭素数１〜６
のアルキル基が挙げられ、これらのアルキル基は直鎖状
でも分岐状でもよい。(In the formula, R1, R2 and R'' represent a hydrogen atom, a lower alkyl group or a lower alkoxycarbonyl group,
l and X3 represent a lower alkyl group or a halogen atom; 12. m and n represent an integer of 0 to 5, zp- represents an anion, and p represents 1 or 2.> In general formula (I), the lower alkyl group represented by R1, R2 and R3 is, 1 to 6 carbon atoms such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.
These alkyl groups may be linear or branched.
また、低級アルコキシカルボニル基としては、メトキシ
カルボニル基、エトキシカルボニル基、プロポキシカル
ボニル基、ブトキシカルボニル基、ペンチルオキシカル
ボニル基、ヘキシルオキシカルボニル基等の総炭素数２
〜６のアルコキシカルボニル基が挙げられる。In addition, examples of lower alkoxycarbonyl groups include methoxycarbonyl groups, ethoxycarbonyl groups, propoxycarbonyl groups, butoxycarbonyl groups, pentyloxycarbonyl groups, and hexyloxycarbonyl groups with a total carbon number of 2.
-6 alkoxycarbonyl groups.
Ｘ’ 、Ｘｔ及びＸ３で表わされる低級アルキル基とし
ては、メチル基、エチル基、プロピル基、ブチル基、ペ
ンチル基、ヘキシル基等の炭素数１〜６のアルキル基が
挙げられ、これらのアルキル基は直鎖状でも分岐状でも
よい。Examples of the lower alkyl group represented by X', Xt and may be linear or branched.
ｚｐ−で表わされる陰イオンとしては、例えばヒ、Ｂｒ
−１Ｃ１−１Ｆ−１Ｃ１○４−１ＢＦ、−（ＣＨｚＣＯ
ＣＩｈＣＯＣＩｈ） −Ｈ
ＣＨｚＣＨＣＯＯ−
Ｈ
ＳｉＦ６” 、５ＯＪＨｚ−ｓ ５ｂＦ６− ％
ＺｒＦ＋、”＼Ｃ１：１Ｈ３ＳＯＺＢ （
◎）・−
ｈＰＯ２−
ＣＯＯ−
０３−
等の一価または二価の陰イオンが挙げられ、好ましくは
Ｉ −、Ｂ ｒ −、Ｃｌ −、Ｐ Ｆ ｂ−ＣＩ Ｏ
−ＢＦ、−１ＢｂＦ、−の陰イオンが挙げられる。Examples of the anion represented by zp- include H, Br,
-1C1-1F-1C1○4-1BF, -(CHzCO
CIhCOCIh) -H CHzCHCOO- H SiF6", 5OJHz-s 5bF6- %
Monovalent or divalent anions such as ZrF+, "\C1:1H3SOZB (◎)・- hPO2- COO- 03- are mentioned, and preferably I -, B r -, Cl -, P F b-CIO
-BF, -1BbF, - anions are mentioned.
前記一般式（１）で示されるアズレン系化合物は、６０
０〜８００ ｎｍの波長帯域で吸光を有し、しかも分子
吸光係数が１０４〜１０’ＣＩ−’である。The azulene compound represented by the general formula (1) has 60
It has absorption in the wavelength band of 0 to 800 nm, and has a molecular extinction coefficient of 104 to 10'CI-'.
本発明に係る一般式［Ｉ］で示されるアズレン系化合は
、例えば一般式〔■］
（式中、Ｒ１、Ｒｚ 、 Ｒ３，ＸＩ 、ＸＩ 、Ｘ
３１、ｍ及びｎは前記定義に同じ。）
で表わされる化合物をジシアノジクロロキノン（ＤＤＱ
）で処理して得られた溶液に、下記一般式
（式中、Ｚ及びｐは前記定義に同じ）
と反応させることにより製造することができる。The azulene compound represented by the general formula [I] according to the present invention is, for example, the general formula [■] (wherein R1, Rz , R3, XI , XI , X
31, m and n are the same as defined above. ) The compound represented by dicyanodichloroquinone (DDQ
) is reacted with the following general formula (wherein Z and p are the same as defined above).
有機溶媒としては、メタノール、エタノール、プロパツ
ール、ブタノール等のアルコール系溶媒、アセトン、メ
チルエチルケトン等のケトン系溶媒、ベンゼン、トルエ
ン、キシレン等の芳香族系溶媒、ジクロロメタン、トリ
クロロエタン等のハロゲン化炭化水素系溶媒等が挙げら
れ、特にトルエン−ブタノール、ベンゼン−ブタノール
等の混合溶媒が好適である。Examples of organic solvents include alcohol solvents such as methanol, ethanol, propatool, and butanol, ketone solvents such as acetone and methyl ethyl ketone, aromatic solvents such as benzene, toluene, and xylene, and halogenated hydrocarbon solvents such as dichloromethane and trichloroethane. Examples include solvents, and mixed solvents such as toluene-butanol and benzene-butanol are particularly suitable.
次に、このような本発明に係るアズレン系化合物を含有
する記録層を有する本発明の光学記録媒体について説明
する。Next, the optical recording medium of the present invention having a recording layer containing the azulene compound according to the present invention will be described.
本発明の光学記録媒体は、基本的には基板とア（Ｘ’）
、ｌ
ズレン系化合物を含む記録層とから構成され、さらに必
要に応じて基板上に下引き層を、また記録層上に保護層
又は金属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 (X')
, l, and a recording layer containing a durene-based compound, and if necessary, an undercoat layer may be provided on the substrate, and a protective layer or a metal layer may be provided on the recording layer.
基板としては、ガラス、プラスチック、紙、板状または
箔状の金属等の一般の記録材料の支持体として用いられ
るものが挙げられるが、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
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、エポキシ樹脂
、ポリサルホン樹脂等が挙げられる。Examples of the substrate include those used as supports for general recording materials, such as glass, plastic, paper, plate-shaped or foil-shaped metal, and plastic is preferred from various points of view. Plastics include acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin,
Examples include polycarbonate resin, polyimide resin, epoxy resin, polysulfone resin, and the like.
光学記録媒体における情報記録層の膜厚は１００人〜５
μｍ、好ましくは５００人〜３μｍである。The thickness of the information recording layer in an optical recording medium is 100 to 5
μm, preferably 500 to 3 μm.
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、浸漬法等一般
に行なわれている薄膜形成法で成膜することができる。The film can be formed by a commonly used thin film forming method such as a vacuum evaporation method, a sputtering method, a doctor blade method, a casting method, a spinner method, or a dipping method.
また、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ポリビニルアルコール、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、バインダー
に対するアズレン系化合物の量は重量比で０．０１以上
であることが望ましい。Moreover, a binder can also be used if necessary. As the binder, known binders such as polyvinyl alcohol, nitrocellulose, cellulose acetate, polyvinyl butyral, and polycarbonate can be used, and the amount of the azulene compound to the binder is preferably 0.01 or more by weight.
スピナー法による成膜の場合、回転数は５００〜５００
０ｒｐｍ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
もよい。In the case of film formation by spinner method, the rotation speed is 500 to 500
0 rpm is preferable, and after the spin code, treatment such as heating or exposure to solvent vapor may be performed depending on the case.
また、記録体の安定性や耐好性向上のために、−重積酸
素クエンチャーとして遷移金属キレート化合＠！Ｊ（た
とえば、アセチルアセトナートキレート、ビスフエニル
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）を含有していてもよい。In addition, in order to improve the stability and resistance of recording media, transition metal chelate compounds@! are used as stacked oxygen quenchers. J (for example, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-α-diketone, etc.).
更に、必要に応じて他の色素を併用することができる。Furthermore, other dyes can be used in combination as necessary.
他の色素としては別の種類の同系統の化合物でもよいし
、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、含金属インドアニリン系色
素など他系統の色素でもよい。The other dyes may be other types of compounds of the same type, or may be dyes of other types such as triarylmethane dyes, azo dyes, cyanine dyes, squarylium dyes, and metal-containing indoaniline dyes.
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、テトラクロロエタン、ブロ
モホルム、ジブロモエタン、エチルセロソルブ、キシレ
ン、クロロベンゼン、シクロヘキサノン、ジアセトンア
ルコール、３−ヒドロキシ−３−メチル−２−ブタノン
等の沸点１２０〜１６０℃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 cast method, a spinner method, or a dipping method, in particular, a spinner method, the coating solvent may be tetrachloroethane, bromoform, dibromoethane, ethyl cellosolve, xylene, chlorobenzene, or cyclohexanone. , diacetone alcohol, 3-hydroxy-3-methyl-2-butanone and the like having a boiling point of 120 to 160°C are preferably used.
光学記録媒体の記録層は基板の両面に設けてもよいし、
片面だけに設けてもよい。The recording layer of the optical recording medium may be provided on both sides of the substrate,
It may be provided only on one side.
上記のようにして得られた光学記録媒体への記録は、基
体の両面または、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、半導体レーザーの光を
あてることにより行なう。Recording on the optical recording medium obtained as described above is carried out by irradiating the recording layer provided on both sides or one side of the substrate with laser light, preferably semiconductor laser light, focused to about 1 μm.
レーザー光の照射された部分には、レーザーエネルギー
の吸収によって、分解、蒸発、溶融等の記録層の熱的変
形が起こる。In the portion irradiated with the laser beam, thermal deformation of the recording layer such as decomposition, evaporation, and melting occurs due to absorption of laser energy.
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
み取ることにより行なう。The recorded information is reproduced by using a laser beam to read the difference in reflectance between a portion where thermal deformation has occurred and a portion where no thermal deformation has occurred.
光学記録媒体に使用されるレーザー光はＮ２、Ｈｅ−Ｃ
＋Ｌ Ａｒｓ Ｈｅ−Ｎｅ、ルビー、半導体、色素レー
ザー等が挙げられるが、特に、軽量性、取扱いの容易さ
、コンパクト性などの点から半導体レーザーが好適であ
る。The laser beam used for optical recording media is N2, He-C
Examples include +L Ars He-Ne, ruby, semiconductor, and dye lasers, but semiconductor lasers are particularly preferred in terms of lightness, ease of handling, and compactness.
〔実施例〕
以下、実施例により本発明を具体的に説明するが、本発
明はその要旨を超えない限り実施例により限定されるも
のではない。[Examples] Hereinafter, the present invention will be specifically explained using Examples, but the present invention is not limited by the Examples unless the gist thereof is exceeded.
実施例１
（ａｌ 製造例
下記構造式
で表わされる化合物５６９．１ ｒｒｘｒ （１，００
ｍｍｏｌ）、をアルゴンガス雰囲気下ジクロロメタン１
００ｃａｌに溶解した溶液に、室温下撹拌しなからＤＤ
Ｑ２５０．５■（１，０９問ｏ１）を加え、さらに室温
下で１時間撹拌した。得られた深青色溶液に６０重量％
ＨＰＦ、溶液１０＋ｗｌを加え、室温で１５分間激しく
撹拌した。その汲水１００ｎ＋１を加え、不溶物を濾別
後、ジクロロメタン層を水洗し、無水硫酸マグネシウム
で乾燥した。減圧下、ジクロロメタン溶液を約１０ｍ１
まで濃縮した後、ジエチルエーテル５０ｍｍ！を加え、
結晶を析出させた。Example 1 (al Production example Compound 569.1 rrxr (1,00
mmol), dichloromethane 1 under argon gas atmosphere
Add DD to the solution dissolved in 00 cal without stirring at room temperature.
Q250.5■ (1.09 questions o1) was added, and the mixture was further stirred at room temperature for 1 hour. 60% by weight in the resulting deep blue solution
HPF, solution 10+wl was added and stirred vigorously at room temperature for 15 minutes. After adding 100 n+1 of the pumped water and filtering off insoluble matter, the dichloromethane layer was washed with water and dried over anhydrous magnesium sulfate. About 10ml of dichloromethane solution under reduced pressure
After concentrating to 50mm of diethyl ether! Add
Crystals were precipitated.
得られた紫色の粉末をジエチルエーテルで洗浄した後、
減圧下６０℃で乾燥して下記構造式で表わされるアズレ
ン系化合物７１３．６■を得た。（収率１００％）
〔物性値〕
融点 ３００℃以上
λｓａｗ （クロロホルム） ６０９ｎｍε（分
子吸光係数”） ６．４Ｘ１０’（ｂ） 記録
媒体例
上記製造例で製造したアズレン系化合物０．１ ｇをエ
チルセロソルブ１０ｇに溶解し、０．２２μｍのフィル
ターで濾過し、溶液を得た。この溶液１ｎ＋Ｊをポリメ
チルメタクリレ−） （ＰＭＭＡ）樹脂基板（直径５２
ｆｉ）の上に滴下し、スピナー法により８００ｒｐｍの
回転数で塗布した。塗布後、６０℃で１０分間乾燥して
、厚さ約７００人の塗布膜を形成した。After washing the obtained purple powder with diethyl ether,
The mixture was dried at 60° C. under reduced pressure to obtain 713.6× of an azulene compound represented by the following structural formula. (Yield 100%) [Physical properties] Melting point 300°C or higher λsaw (chloroform) 609 nmε (molecular extinction coefficient) 6.4X10' (b) Example of recording medium 0.1 g of the azulene compound produced in the above production example was dissolved in ethyl It was dissolved in 10 g of Cellosolve and filtered through a 0.22 μm filter to obtain a solution. This solution 1n+J was poured onto a polymethyl methacrylate (PMMA) resin substrate (diameter 52
fi) and applied by a spinner method at a rotation speed of 800 rpm. After coating, it was dried at 60° C. for 10 minutes to form a coating film with a thickness of about 700 mm.
（Ｃ１光記録法
上記記録媒体例で得られた塗布膜に、中心波長６３３ｎ
ｎ＋のＨｅ −Ｎ ｅレーザー光を出力４−で照射した
ところ、輪郭の極めて明瞭なビットが形成した。(C1 optical recording method) The coating film obtained in the above recording medium example was coated with a center wavelength of 633 nm.
When irradiated with n+ He-Ne laser light at an output of 4-, a bit with an extremely clear outline was formed.
実施例２
（ａ） 製造例
下記構造式
アズレン系化合物５８０．０■を得た。（収率１００％
）
で表わされる化合物４３６．２ ｍｇ （１，ＯＯｍｍ
ｏｌ）をアルゴンガス雰囲気下ジクロロメタン１００ｒ
ａｌに溶解した溶液に、室温下撹拌しながらＤＤＱ２５
１、７ ｔｇ （１，１０ｍｎ＋ｏｌ）を加え、さらに
室温で１時間撹拌した。得られた深青色溶液に６０重量
％ＨＰＦ、溶液１０ｍｊ＋を加え１５分間激しく撹拌し
た。その後、水１００ｍｊ！を加え不溶性物質を濾別後
、ジクロロメタン層を水洗し、無水硫酸マグネシウムで
乾燥した。減圧下、ジクロロメタン溶液を約１０ｍｌ１
まで濃縮後、ジエチルエーテル５０ｎ＋４２を加え、結
晶を析出させた。得られた帯揚紫色の粉末をジエチルエ
ーテルで洗浄した後、減圧下６０℃で乾燥して下記構造
式で表わされる〔物性値〕
融点 ３００℃以上
λ□Ｘ （クロロホルム） ６６０ｎｍ８（分子吸
光係数） ４．４Ｘ１０’（ｂ） 記録媒体例
上記製造例で製造したアズレン系化合物０．１ｇを３−
ヒドロキシ−３−メチル−２−ブタノン１０ｇに溶解し
、０．２２μｍのフィルターで濾過し、溶液を得た。こ
の溶液１ ｍｌをポリカーボネート樹脂基板（直径５２
ｆｌ）の上に滴下し、スピナー法により８００ｒｐｍの
回転数で塗布した。塗布後、６０℃で１０分間乾燥して
、厚さ約７００人の塗布膜を形成した。Example 2 (a) Production Example An azulene compound with the following structural formula (580.0) was obtained. (Yield 100%
) Compound 436.2 mg (1,OOmm
ol) in dichloromethane 100r under an argon gas atmosphere.
Add DDQ25 to the solution dissolved in al while stirring at room temperature.
1,7 tg (1,10 mn+ol) was added, and the mixture was further stirred at room temperature for 1 hour. To the obtained deep blue solution, 60% by weight HPF and solution 10mj+ were added and stirred vigorously for 15 minutes. After that, 100mj of water! After adding and filtering off insoluble substances, the dichloromethane layer was washed with water and dried over anhydrous magnesium sulfate. Under reduced pressure, add about 10 ml of dichloromethane solution.
After concentrating to 90%, 50n+42 diethyl ether was added to precipitate crystals. The obtained purple powder was washed with diethyl ether and then dried at 60°C under reduced pressure to obtain a product represented by the following structural formula [Physical properties] Melting point 300°C or higher λ□X (chloroform) 660 nm8 (molecular extinction coefficient) 4.4X10'(b) Recording medium example 0.1 g of the azulene compound produced in the above production example was
It was dissolved in 10 g of hydroxy-3-methyl-2-butanone and filtered through a 0.22 μm filter to obtain a solution. Transfer 1 ml of this solution to a polycarbonate resin substrate (diameter 52
fl) and applied by a spinner method at a rotation speed of 800 rpm. After coating, it was dried at 60° C. for 10 minutes to form a coating film with a thickness of about 700 mm.
（Ｃ） 光記録法
上記記録媒体例で得られた塗布膜に、中心波長６３３ｎ
ｍのＨｅ−Ｎｅレーザー光を出力４ｍ−で照射したとこ
ろ、輪郭の極めて明瞭なピントが形成した。(C) Optical recording method The coating film obtained in the above recording medium example was coated with a center wavelength of 633 nm.
When the image was irradiated with a He-Ne laser beam having an output of 4 m, an extremely clear focus was formed.
実施例３
（ａ） 製造例
下記構造式
拌した。その後、水５０ｍｆを加え、不溶性物質を濾別
後、ジクロロメタン層を水洗し、無水硫酸マグネシウム
で乾燥した。減圧下、ジクロロメタン溶液を約１０ｍ１
まで濃縮後、ジエチルエーテル５０ｍＪを加え、結晶を
析出させた。得られた褐色の粉末をジエチルエーテルで
洗浄した後、減圧下６０℃で乾燥し、下記構造式で表わ
されるアズレン系化合物３８．０■を得た。（収率５５
．６％）で表わされる化合物５０．ｌ■をアルゴンガス
雰囲気下ジクロロメタンに溶解した溶液に、室温下撹拌
しなからＤＤＱ１５．８■を加え、さらに室温で１時間
撹拌した。得られた深青色溶液に６０重量％ＨＰＦ６溶
液４ ｒａｌを加え、１５分間激しく撹〔物性値〕
融点 ３００℃以上
（ｂ） 記録媒体例
上記製造例で製造したアズレン系化合物０．１ｇをテト
ラクロロエタン１０ｇに溶解し、０．２２μｍのフィル
ターで濾過し、溶液を得た。この溶液１ ｍｌをＰＭＭ
Ａ樹脂基板（直径５２ｎ）の上に滴下し、スピナー法に
より８００ｒｐｍの回転数で塗布した。塗布後、６０℃
で１０分間乾燥して、厚さ約７００人の塗布膜を形成し
た。Example 3 (a) Production Example The following structural formula was stirred. Thereafter, 50 mf of water was added, and after filtering off insoluble substances, the dichloromethane layer was washed with water and dried over anhydrous magnesium sulfate. About 10ml of dichloromethane solution under reduced pressure
After concentration, 50 mJ of diethyl ether was added to precipitate crystals. The obtained brown powder was washed with diethyl ether and then dried at 60° C. under reduced pressure to obtain 38.0× of an azulene compound represented by the following structural formula. (Yield 55
．． 6%) Compound 50. 15.8 ■ of DDQ was added to a solution of 1■ in dichloromethane under an argon gas atmosphere while stirring at room temperature, and the mixture was further stirred at room temperature for 1 hour. Add 4 ral of 60 wt% HPF6 solution to the obtained deep blue solution and stir vigorously for 15 minutes [Physical properties] Melting point 300°C or higher (b) Example of recording medium 0.1 g of the azulene compound produced in the above production example was added to tetrachloroethane. It was dissolved in 10 g and filtered through a 0.22 μm filter to obtain a solution. Add 1 ml of this solution to PMM
It was dropped onto a resin substrate A (diameter 52 nm) and coated at a rotation speed of 800 rpm using a spinner method. After application, 60℃
The coating was dried for 10 minutes to form a coating film with a thickness of approximately 700 mm.
（Ｃ） 光記録法
上記記録媒体例で得られた塗布膜に、中心波長６３３ｎ
ｎ＋のＨｅ−Ｎｅレーザー光を出力４１ｍ−で照射した
ところ、輪郭の極めて明瞭なビットが形成した。(C) Optical recording method The coating film obtained in the above recording medium example was coated with a center wavelength of 633 nm.
When irradiated with n+ He--Ne laser light at an output of 41 m-, a bit with an extremely clear outline was formed.
本発明の光学記録媒体は、塗布あるいは蒸着により記録
層を形成することができ、記録層にレーザー光を照射す
ると輪郭の極めて明瞭なピントが形成される等、光学記
録媒体として優れており、工業的に有用である。The optical recording medium of the present invention has a recording layer formed by coating or vapor deposition, and when the recording layer is irradiated with a laser beam, an extremely clear focus is formed, making it excellent as an optical recording medium and suitable for industrial use. useful.
第１図は実施例１の製造例で得られたアズレン系化合物
のクロロホルム溶液中の可視部の吸収スペクトルを示し
た図、第２図は実施例２の製造例で得られたアズレン系
化合物のクロロホルム溶液中の可視部の吸収スペクトル
を示した図である。Figure 1 shows the absorption spectrum of the azulene compound obtained in the production example of Example 1 in the visible region in a chloroform solution, and Figure 2 shows the absorption spectrum of the azulene compound obtained in the production example of Example 2. FIG. 3 is a diagram showing an absorption spectrum in the visible region in a chloroform solution.
Claims (1)
記録する記録層を有する光学記録媒体において、該記録
層が一般式〔 I 〕 ▲数式、化学式、表等があります▼・・・〔 I 〕 （式中、Ｒ＾１、Ｒ＾２及びＲ＾３は水素原子、低級ア
ルキル基又は低級アルコキシカルボニル基を表わし、Ｘ
＾１、Ｘ＾２及びＸ＾３は低級アルキル基又はハロゲン
原子を表わし、ｌ、ｍ及びｎは０〜５の整数を表わす。 Ｚ＾ｐ＾−は陰イオンを表わし、ｐは１又は２を表わす
。）で示されるアズレン系化合物を含有することを特徴
とする光学記録媒体。(1) In an optical recording medium that has a recording layer that records information by changing its optical properties by irradiation with light, the recording layer has a general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[ I] (In the formula, R^1, R^2 and R^3 represent a hydrogen atom, a lower alkyl group or a lower alkoxycarbonyl group,
^1, X^2 and X^3 represent a lower alkyl group or a halogen atom, and l, m and n represent an integer of 0 to 5. Z^p^- represents an anion, and p represents 1 or 2. ) An optical recording medium characterized by containing an azulene compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1212455A JPH0376685A (en) | 1989-08-18 | 1989-08-18 | Optical recording medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1212455A JPH0376685A (en) | 1989-08-18 | 1989-08-18 | Optical recording medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0376685A true JPH0376685A (en) | 1991-04-02 |
Family
ID=16622910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1212455A Pending JPH0376685A (en) | 1989-08-18 | 1989-08-18 | Optical recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0376685A (en) |
-
1989
- 1989-08-18 JP JP1212455A patent/JPH0376685A/en active Pending
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