JP4178783B2 - Optical recording medium - Google Patents
Optical recording medium Download PDFInfo
- Publication number
- JP4178783B2 JP4178783B2 JP2001322562A JP2001322562A JP4178783B2 JP 4178783 B2 JP4178783 B2 JP 4178783B2 JP 2001322562 A JP2001322562 A JP 2001322562A JP 2001322562 A JP2001322562 A JP 2001322562A JP 4178783 B2 JP4178783 B2 JP 4178783B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- layer
- optical recording
- recording
- recording medium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical group C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- APHCVEVLYBPWIK-UHFFFAOYSA-N n-(2-hydroxyphenyl)nitrous amide Chemical compound OC1=CC=CC=C1NN=O APHCVEVLYBPWIK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
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- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
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- XTVMZZBLCLWBPM-UHFFFAOYSA-N tert-butylcyclohexane Chemical compound CC(C)(C)C1CCCCC1 XTVMZZBLCLWBPM-UHFFFAOYSA-N 0.000 description 1
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
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Landscapes
- Optical Record Carriers And Manufacture Thereof (AREA)
- Optical Recording Or Reproduction (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Quinoline Compounds (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、有機色素を記録層に用いた追記型光学記録媒体に係わるものであり、詳しくは青色レーザー対応の追記型光学記録媒体に関するものである。
【０００２】
【従来の技術】
近年、発振波長の短い半導体レーザーの開発が進められ、従来使用されているレーザーの波長780nm、830nmよりも短波長のレーザー光を用いた高密度の記録再生可能な光学記録媒体が求められている。従来提案されている光学記録媒体としては、光磁気記録媒体、相変化記録媒体、カルコゲン酸化物光記録媒体、有機色素系光記録媒体等があるが、これらの中で有機色素系光記録媒体は、コスト的に安価で且つ製造プロセス工程も容易であるという点で優位性を有するものと考えられている。
【０００３】
現在、有機色素系光学記録媒体には、反射率の高い金属層を有機色素層の上に積層したタイプの書き込み型コンパクトディスク（ＣＤ−Ｒ）が量産化され広く知られているが、このＣＤ−Ｒの記録再生に使用されるレーザーよりもさらに短波長の赤色半導体レーザーで記録する高密度の有機色素系光学記録媒体（ＤＶＤ−Ｒ）も開発され、実用化されている。しかし、より短波長のレーザー発振が可能になるに従い、今後、更により一層の高密度化を狙って、ＤＶＤ−Ｒよりもさらに短波長のレーザー、即ち青色半導体レーザー（波長350nm〜530nm）で記録再生可能な光学記録媒体の必要性が高まってくる。
【０００４】
【発明が解決しようとする課題】
一般に、ＣＤ−Ｒ或いはＤＶＤ−Ｒとして使用されている光学記録媒体は、短波長の青色半導体レーザーで記録再生すると、反射率が低く記録再生ができないという問題を有している。
この様な課題に対し、例えば特開２００１−９６９１８号公報では、７位にアミノ基を有するカルボスチリル化合物を含有する記録層を有する光学記録媒体が開示されている。しかしながら、本発明者らの検討によると、特開２００１−９６９１８号公報に記載されているカルボスチリル化合物を記録層として用いた場合、成膜時に結晶化が起こり記録層として十分な反射率が得られないことがわかった。この問題点を解決するために、鋭意検討を行った結果、特定の構造のカルボスチリル化合物を記録層として用いることによって、結晶化が起こらない良好な記録層が得られることを見いだした。
本発明は、青色半導体レーザーによって記録再生が可能な有機色素系光学記録媒体を提供することを目的とする。
【０００５】
【課題を解決するための手段】
本発明者らは青色半導体レーザーに高い感受性を有する有機色素について種々検討した結果、特定の構造式で表されるカルボスチリル誘導体が、青色半導体レーザーに対応する光学記録媒体の記録層に使用し得ることを知得し本発明に到達した。
【０００６】
すなわち本発明の要旨は、基板上に、レーザーによる情報の記録及び／又は再生が可能な記録層が設けられた光学記録媒体であって、該記録層に、下記一般式［Ｉ］で示されるカルボスチリル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。
【０００７】
【化２】
（式中、Ｘは窒素原子またはＣ−Ｒ６を表す。Ｒ１は置換基を有していてもよいアルキル基、シクロアルキル基、アルケニル基、シクロアルケニル基、アラルキル基、アリール基、飽和もしくは不飽和の複素環基、アシル基から選ばれる基を表す。Ｒ ２ 及びＲ ４ は水素原子を表し、Ｒ ５ はＲ ８ とＲ ５ が環を形成する場合を除き、水素原子であり、Ｒ ６ はＲ ７ とＲ ６ が環を形成する場合を除き、水素原子である。Ｒ３は置換基を有していてもよいアルキル基、シクロアルキル基、アルケニル基、シクロアルケニル基、アルコキシ基、アルキルチオ基、アラルキル基、アルケニルオキシ基、アリール基、飽和もしくは不飽和の複素環基、ハロゲン原子、ニトロ基、シアノ基、ホルミル基、ヒドロキシ基、カルボキシル基、スルホン酸基、アミノ基、アシルアミノ基、カーバメート基、スルホンアミド基、カルバモイル基、カルボン酸エステル基、スルファモイル基及びスルホン酸エステル基から選ばれる基である。Ｒ７およびＲ８は、各々独立に置換基を有してもよいアルキル基、アルケニル基、アラルキル基、又はアシル基であるか、Ｒ７とＲ８が結合せず、Ｒ７とＲ６、及びＲ８とＲ５の１以上が結合して環を形成していてもよい。）
【０００９】
【発明の実施の形態】
以下本発明につき詳細に説明する。
本発明で使用される前記一般式［Ｉ］の化合物は、３５０〜５３０nmの青色光波長領域に適度な吸収を有し、青色レーザー光での記録に適する色素である。
前記一般式（１）において、Ｒ1は置換基を有していてもよいアルキル基、シクロアルキル基、アルケニル基、シクロアルケニル基、アラルキル基、アリール基、飽和もしくは不飽和の複素環基、アシル基から選ばれる基を表す置換基であるが、中でも好ましい置換基としては次のようなものが例示される。メチル基、エチル基、プロピル基、イソプロピル基、n-ブチル基、sec-ブチル基、tert-ブチル基、n-へプチル基等の炭素数１〜１８の直鎖又は分岐のアルキル基；シクロプロピル基、シクロペンチル基、シクロヘキシル基、アダマンチル基等の炭素数３〜１８のシクロアルキル基；ビニル基、プロペニル基、ヘキセニル基等の炭素数２〜１８の直鎖又は分岐のアルケニル基；シクロペンテニル基、シクロヘキセニル基等の炭素数３〜１８のシクロアルケニル基；2-チエニル基、2-ピリジル基、フリル基、チアゾリル基、ベンゾチアゾリル基、モルホリノ基、ピロリジニル基、テトラヒドロチオフェンジオキサイド基等の飽和もしくは不飽和の複素環基；フェニル基、トリル基、キシリル基、メシチル基等の炭素数６〜１８のアリール基；ベンジル基、フェネチル基等の炭素数７〜２０のアラルキル基；アセチル基、プロピオニル基、ブチリル基、イソブチリル基、バレリル基、イソバレリル基等の炭素数２〜１８の直鎖又は分岐のアシル基等が挙げられる。
カルボスチリル化合物の置換基Ｒ ２ 及びＲ ４ は水素原子を表し、Ｒ ５ はＲ ８ とＲ ５ が環を形成する場合を除き、水素原子であり、Ｒ ６ はＲ ７ とＲ ６ が環を形成する場合を除き、水素原子である。
Ｒ 3 は置換基を有していてもよいアルキル基、シクロアルキル基、アルケニル基、シクロアルケニル基、アルコキシ基、アルキルチオ基、アラルキル基、アルケニルオキシ基、アリール基、飽和もしくは不飽和の複素環基、ハロゲン原子、ニトロ基、シアノ基、ホルミル基、ヒドロキシ基、カルボキシル基、スルホン酸基、アミノ基、アシルアミノ基、カーバメート基、スルホンアミド基、カルバモイル基、カルボン酸エステル基、スルファモイル基及びスルホン酸エステル基から選ばれる基である。Ｒ 3 で表される置換基としては次のようなものが例示される。メチル基、エチル基、プロピル基、イソプロピル基、n-ブチル基、sec-ブチル基、tert-ブチル基、n-へプチル基等の炭素数１〜１８の直鎖又は分岐のアルキル基；シクロプロピル基、シクロペンチル基、シクロヘキシル基、アダマンチル基等の炭素数３〜１８のシクロアルキル基；ビニル基、プロペニル基、ヘキセニル基等の炭素数２〜１８の直鎖又は分岐のアルケニル基；シクロペンテニル基、シクロヘキセニル基等の炭素数３〜１８のシクロアルケニル基；2-チエニル基、2-ピリジル基、フリル基、チアゾリル基、ベンゾチアゾリル基、モルホリノ基、ピロリジニル基、テトラヒドロチオフェンジオキサイド基等の飽和もしくは不飽和の複素環基；フェニル基、トリル基、キシリル基、メシチル基等の炭素数６〜１８のアリール基；ベンジル基、フェネチル基等の炭素数７〜２０のアラルキル基；メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基、n-ブトキシ基、sec-ブトキシ基、tert-ブトキシ基等の炭素数１〜１８の直鎖または分岐のアルコキシ基；プロペニルオキシ基、ブテニルオキシ基、ペンテニルオキシ基等の炭素数３〜１８の直鎖または分岐のアルケニルオキシ基；メチルチオ基、エチルチオ基、n-プロピルチオ基、n-ブチルチオ基、sec-ブチルチオ基、tert-ブチルチオ基等の炭素数１〜１８の直鎖または分岐のアルキルチオ基；フッ素原子、塩素原子、臭素原子等のハロゲン原子；ニトロ基；シアノ基；ヒドロキシ基；ホルミル基；スルホン酸基；カルボキシル基；−ＮＲ10Ｒ11で表されるアミノ基；−ＮＨＣＯＲ12で表されるアシルアミノ基；−ＮＨＣＯＯＲ13で表されるカーバメート基；−ＮＨＳＯ2Ｒ14で表されるスルホンアミド基；−ＣＯＯＲ15で表されるカルボン酸エステル基；−ＣＯＮＲ16Ｒ17で表されるカルバモイル基；−ＳＯ2ＮＲ18Ｒ19で表されるスルファモイル基；−ＳＯ3Ｒ20で表されるスルホン酸エステル基等が挙げられる。Ｒ 10 〜Ｒ 20 はそれぞれ水素原子、置換されても よい直鎖、分岐または環状のアルキル基、置換されてもよい直鎖、分岐または環状のアルケニル基、置換されてもよいアリール基、または置換されてもよいアラルキル基を表す。
Ｒ 3 、Ｒ 7 及びＲ 8 は、青色レーザーによる記録に適する吸収スペクトルを有するための置換基であり、Ｒ 7 およびＲ 8 が、各々独立に置換基を有していてもよいアルキル基、アルケニル基、アラルキル基、又はアシル基であるか、Ｒ ７ とＲ ８ が結合せず、Ｒ ７ とＲ ６ 、及びＲ ８ とＲ ５ の１以上が結合して環を形成していてもよい。
Ｒ 7 およびＲ 8 で表されるアルキル基、アルケニル基、アラルキル基としては上述したＲ 3 において例示したものと同様なものが挙げられる。一方、アシル基としては、アセチル基、プロピオニル基、ブチリル基、イソブチリル基、バレリル基、イソバレリル基等の炭素数２〜１８の直鎖又は分岐のアシル基が挙げられる。Ｒ 7 およびＲ 8 としてより好ましくは炭素数１〜６の直鎖または分岐のアルキル基、炭素数７〜１８のアラルキル基、炭素数２〜１８直鎖または分岐のアルケニル基、アシル基、あるいはＲ ７ とＲ ６ 、またはＲ ８ とＲ ５ が結合して形成した飽和複素環である。中でも特に好ましくは炭素数１〜６の直鎖または分岐のアルキル基である。
【００１０】
Ｒ ３ 、Ｒ ７ 及びＲ ８ で表される複数の置換基は同種でも異なってもよい。またＲ ７ とＲ ８ が結合せず、Ｒ ７ とＲ ６ 、及びＲ ８ とＲ ５ の１以上が結合して環を形成する場合としては、基本骨格であるキノリン環に縮合し、複素環、或いはＲ ７ とＲ６、及びＲ８とＲ５の１以上が結合して形成するジュロリジン環等が挙げられる。これらの環はさらに置換基を有していても良い。
【００１３】
Ｒ 1 〜Ｒ 20 （ただし、Ｒ ２ 、Ｒ ４ 、Ｒ ５ 、Ｒ ６ を除く）で示される基に含まれるアルキル基、アルケニル基、アリール基、複素環基は、更に置換されていても良い。この場合の置換基としては、メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基、n-ブトキシ基、sec-ブトキシ基、tert-ブトキシ基等の炭素数１〜１０のアルコキシ基；メトキシメトキシ基、エトキシメトキシ基、プロポキシメトキシ基、エトキシエトキシ基、プロポキシエトキシ基、メトキシブトキシ基等の炭素数２〜１２のアルコキシアルコキシ基；メトキシメトキシメトキシ基、メトキシメトキシエトキシ基、メトキシエトキシメトキシ基、メトキシメトキシエトキシ基、エトキシエトキシメトキシ基等の炭素数３〜１５のアルコキシアルコキシアルコキシ基；アリルオキシ基；フェニル基、トリル基、キシリル基等の炭素数６〜１２のアリール基（これらは置換基でさらに置換されていてもよい。）；フェノキシ基、トリルオキシ基、キシリルオキシ基、ナフチルオキシ基等の炭素数６〜１２のアリールオキシ基；アリルオキシ基、ビニルオキシ基等の炭素数２〜１２のアルケニルオキシ基；アセチル基、プロピオニル基等のアシル基；シアノ基；ニトロ基；ヒドロキシル基；テトラヒドロフリル基；アミノ基；Ｎ，Ｎ−ジメチルアミノ基、Ｎ，Ｎ−ジエチルアミノ基等の炭素数１〜１０のアルキルアミノ基；メチルスルホニルアミノ基、エチルスルホニルアミノ基、n-プロピルスルホニルアミノ基等の炭素数１〜６のアルキルスルホニルアミノ基；フッ素原子、塩素原子、臭素原子等のハロゲン原子；メトキシカルボニル基、エトキシカルボニル基、n-プロポキシカルボニル基、イソプロポキシカルボニル基、n-ブトキシカルボニル等の炭素数２〜７のアルコキシカルボニル基；メチルカルボニルオキシ基、エチルカルボニルオキシ基、n-プロピルカルボニルオキシ基、イソプロピルカルボニルオキシ基、n-ブチルカルボニルオキシ基等の炭素数２〜７のアルキルカルボニルオキシ基；メトキシカルボニルオキシ基、エトキシカルボニルオキシ基、n-プロポキシカルボニルオキシ基、イソプロポキシカルボニルオキシ基、n-ブトキシカルボニルオキシ基等の炭素数２〜７のアルコキシカルボニルオキシ基等が挙げられている。
【００１７】
一般式［Ｉ］で表される化合物の分子量としては、好ましくは２，０００以下、さらに好ましくは１，０００以下である。一般式［Ｉ］で表される化合物の具体的な例としては下記のものが挙げられるが、これらに限定されるものではない。
【００１８】
【化２】
【化３】
【化４】
【化５】
【化６】
【化７】
これら本発明の色素は、例えば該色素を含む溶液から記録層の成膜を形成する際の、薄膜形成性に優れているので、光学記録媒体の記録層に使用する色素として極めて有用である。また本発明の色素は、該色素を含有する記録層がより短い波長（350nm〜530nm）領域にレーザー光による記録再生に適した強度の吸収を有しているため、短波長レーザーに対応する記録再生用光学記録媒体に使用する色素として、極めて有用である。
【００２９】
本発明の光学記録媒体は、基本的には基板と前記化合物を含む記録層とから構成されるものであるが、さらに必要に応じて基板上に下引き層、金属反射層、保護層等を設けても良い。
好ましい層構成の一例としては、基板上に記録層を設け、さらに該記録層上に金、銀、アルミニウムのような金属反射層および保護層を設けた高反射率の媒体、基板上に金、銀、アルミニウムのような金属反射層を設け、さらに該金属反射層上に保護層を設けた高反射率の媒体等が挙げられる。
【００３０】
以下、この構造の媒体を例に、本発明の光学記録媒体について説明する。
本発明の光学記録媒体における基板の材質としては、基本的には記録光及び再生光の波長で透明であればよい。
このような材質としては、例えばアクリル系樹脂、メタクリル系樹脂、ポリカーボネート樹脂、ポリオレフィン系樹脂（特に非晶質ポリオレフィン）、ポリエステル系樹脂、ポリスチレン樹脂、エポキシ樹脂等の樹脂からなるもの、ガラスからなるもの、ガラス上に光硬化性樹脂等の放射線硬化性樹脂からなる樹脂層を設けたもの等を使用することができる。
【００３１】
高生産性、コスト、耐吸湿性などの点からは、射出成型ポリカーボネートが好ましい。
耐薬品性、耐吸湿性などの点からは、非晶質ポリオレフィンが好ましい。
また高速応答などの点からは、ガラス基板が好ましい。
記録層に接して樹脂基板または樹脂層を設け、その樹脂基板または樹脂層上に記録再生光の案内溝やピットを有していてもよい。案内溝がスパイラル状の場合、この溝ピッチが0.2〜1.2μｍ程度であることが好ましい。
基板上、または必要に応じて下引き層等を設けた上に、本発明の化合物を含む記録層を形成する。
【００３２】
記録層の成膜方法としては、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、スピンコート法、浸漬法等一般に行われている薄膜形成法が挙げられる。量産性、コスト面からはスピンコート法が好ましい。また、厚みの均一な記録層が得られるという点からは、塗布法よりも真空蒸着法等の方が好ましい。
【００３３】
スピンコート法による成膜の場合、回転数は500〜15000rpmが好ましく、スピンコートの後、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っても良い。
ドクターブレード法、キャスト法、スピンコート法、浸漬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、基板を侵さない溶媒であればよく、特に限定されない。例えば、ジアセトンアルコール、3-ヒドロキシ-3-メチル-2-ブタノン等のケトンアルコール系溶媒；メチルセロソルブ、エチルセロソルブ等のセロソルブ系溶媒；n-ヘキサン、n-オクタン等の鎖状炭化水素系溶媒；シクロヘキサン、メチルシクロヘキサン、エチルシクロヘキサン、ジメチルシクロヘキサン、n-ブチルシクロヘキサン、tert-ブチルシクロヘキサン、シクロオクタン等の環状炭化水素系溶媒；テトラフルオロプロパノール、オクタフルオロペンタノール、ヘキサフルオロブタノール等のパーフルオロアルキルアルコール系溶媒；乳酸メチル、乳酸エチル、イソ酪酸メチル等のヒドロキシカルボン酸エステル系溶媒等が挙げられる。
【００３４】
真空蒸着法の場合は、例えば本発明の化合物と、必要に応じて他の色素や各種添加剤等の記録層成分を、真空容器内に設置されたるつぼに入れ、真空容器内を適当な真空ポンプで１０-2〜１０-5Ｐａ程度にまで排気した後、るつぼを加熱して記録層成分を蒸発させ、るつぼと向き合って置かれた基板上に蒸着させることにより、記録層を形成する。
また、記録層は、記録層の安定や耐光性向上のために、一重項酸素クエンチャーとして遷移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）等や、記録感度向上のために金属系化合物等の記録感度向上剤を含有していても良い。ここで金属系化合物とは、遷移金属等の金属が原子、イオン、クラスター等の形で化合物に含まれるものを言い、例えばエチレンジアミン系錯体、アゾメチン系錯体、フェニルヒドロキシアミン系錯体、フェナントロリン系錯体、ジヒドロキシアゾベンゼン系錯体、ジオキシム系錯体、ニトロソアミノフェノール系錯体、ピリジルトリアジン系錯体、アセチルアセトナート系錯体、メタロセン系錯体、ポルフィリン系錯体のような有機金属化合物が挙げられる。金属原子としては特に限定されないが、遷移金属であることが好ましい。
さらに、必要に応じて他系統の色素を併用することもできる。他系統の色素としては、主として記録用のレーザー波長域に適度な吸収を有するものであればよく、特に制限されない。また、CD-Rのような770〜830nmから選ばれた波長の近赤外レーザーやDVD-Rのような620〜690nmから選ばれた赤色レーザーでの記録に適する色素を併用して、複数の波長域でのレーザー光による記録に対応する光学記録媒体とすることもできる。
他系統の色素としては含金属アゾ系色素、フタロシアニン系色素、ナフタロシアニン系色素、シアニン系色素、アゾ系色素、スクアリリウム系色素、含金属インドアニリン系色素、トリアリールメタン系色素、メロシアニン系色素、アズレニウム系色素、ナフトキノン系色素、アントラキノン系色素、インドフェノール系色素、キサンテン系色素、オキサジン系色素、ピリリウム系色素等が挙げられる。
さらに、必要に応じて、バインダー、レベリング剤、消泡剤等を併用することもできる。好ましいバインダーとしては、ポリビニルアルコール、ポリビニルピロリドン、ニトロセルロース、酢酸セルロース、ケトン系樹脂、アクリル系樹脂、ポリスチレン系樹脂、ウレタン系樹脂、ポリビニルブチラール、ポリカーボネート、ポリオレフィン等が挙げられる。
【００３５】
記録層の膜厚は、記録方法などにより適した膜厚が異なる為、特に限定するものではないが、通常50〜300nmである。
記録層の上には、反射層を形成してもよく、その膜厚は好ましくは、厚さ50〜300nmである。反射層の材料としては、再生光の波長で反射率の十分高いもの、例えば、Au、Al、Ag、Cu、Ti、Cr、Ni、Pt、Ta、Cr及びPdの金属を単独あるいは合金にして用いることが可能である。この中でもAu、Al、Agは反射率が高く反射層の材料として適している。これらを主成分とする以外に下記のものを含んでいても良い。例えば、Mg、Se、Hf、Ｖ、Nb、Ru、Ｗ、Mn、Re、Fe、Co、Rh、Ir、Cu、Zn、Cd、Ga、In、Si、Ge、Te、Pb、Po、Sn、Biなどの金属及び半金属を挙げることができる。なかでもAgを主成分としているものはコストが安い点、高反射率が出やすい点、更に後で述べる印刷受容層を設ける場合には地色が白く美しいものが得られる点等から特に好ましい。ここで主成分とは含有率が５０％以上のものをいう。
金属以外の材料で低屈折率薄膜と高屈折率薄膜を交互に積み重ねて多層膜を形成し、反射層として用いることも可能である。
【００３６】
反射層を形成する方法としては、例えば、スパッタ法、イオンプレーティング法、化学蒸着法、真空蒸着法等が挙げられる。また、基板の上や反射層の下に反射率の向上、記録特性の改善、密着性の向上等のために公知の無機系または有機系の中間層、接着層を設けることもできる。
反射層の上に形成する保護層の材料としては、反射層を外力から保護するものであれば特に限定されない。有機物質の材料としては、熱可塑性樹脂、熱硬化性樹脂、電子線硬化性樹脂、ＵＶ硬化性樹脂等を挙げることができる。また、無機物質としては、SiO2、Si3N4、MgF2、SnO2等が挙げられる。
熱可塑性樹脂、熱硬化性樹脂などは適当な溶剤に溶解して塗布液を塗布し、乾燥することによって形成することができる。ＵＶ硬化性樹脂は、そのままもしくは適当な溶剤に溶解して塗布液を調製した後にこの塗布液を塗布し、ＵＶ光を照射して硬化させることによって形成することができる。ＵＶ硬化性樹脂としては、例えば、ウレタンアクリレート、エポキシアクリレート、ポリエステルアクリレートなどのアクリレート系樹脂を用いることができる。これらの材料は単独であるいは混合して用いても良いし、１層だけではなく多層膜にして用いても良い。
保護層の形成方法としては、記録層と同様にスピンコート法やキャスト法等の塗布法やスパッタ法や化学蒸着法等の方法が用いられるが、この中でもスピンコート法が好ましい。
【００３７】
保護層の膜厚は、一般に0.1〜100μmの範囲であるが、本発明においては、３〜30μmが好ましい。
以上の説明は、基板／記録層／反射層／保護層の順に積層された基本的層構成を有し、基板を通して照射されたレーザー光により記録・再生を行う光学記録媒体を例に行ったが、本発明の特性を損なわない限り、これら各層の間には任意の層を有していてもよい。
また保護層の上に、あるいは保護層を設けず反射層の上に、接着剤層などを介して更に基板を貼り合わせてもよい。該基板は、何ら層を設けていない基板そのものであっても良く、貼り合わせ面またはその反対面に任意の層を有していてもよい。保護層および／または反射層を対向させて、少なくとも記録層を有する２枚の基板を対向させ、両面記録・再生可能な光学記録媒体としてもよい。
ところで、光学記録媒体の記録密度を上げるための一つの手段として、対物レンズの開口数を上げて情報記録面に集光される光スポットを微少化することが提案されているが、対物レンズの開口数を上げるとディスクの反り等の影響により集光される光スポットの収差が大きくなり、良好な記録再生信号が安定して得られないという問題が存在する。
このような、媒体の反りによって発生する前記収差を小さくするためには、例えば記録・再生用レーザー光が通過する透明基板の厚みを、０．１ｍｍ程度まで薄くするか、基板／反射層／記録層／保護被膜を順次積層してなる光学記録媒体に対し、保護層を通して記録・再生することが好ましい。この保護被膜は、フィルムないしシート状のものを接着剤によって貼り合わせてもよいし、あるいは前述の保護層と同様に、成膜用の塗液を塗布することにより形成しても良い。上記各層間には、本発明の特性を損なわない限り、任意の層を有していてもよい。
上記いずれの順に積層した媒体においても、必要に応じて、記録再生光の入射面ではない面には、インクジェット、感熱転写等の各種プリンタ、或いは各種筆記具にて記入（印刷）が可能な印刷受容層を設けてもよい。
本発明の光学記録媒体について使用されるレーザー光は、高密度記録のため波長は短いほど好ましいが、特に350〜530nmのレーザー光が好ましい。かかるレーザー光の代表例としては、中心波長405nm、410nm、515nmのレーザー光が挙げられる。
【００３８】
波長350〜530nmの範囲のレーザー光の一例は、405nm、410nmの青色または515nmの青緑色の高出力半導体レーザーを使用することにより得ることができるが、その他、例えば、(a)基本発振波長が740〜960nmの連続発振可能な半導体レーザー、または(b)半導体レーザーによって励起され、且つ基本発振波長が740〜960nmの連続発振可能な固体レーザーのいずれかを第二高調波発生素子(SHG)により波長変換することによっても得ることができる。
上記のＳＨＧとしては、反転対称性を欠くピエゾ素子であればいかなるものでもよいが、ＫＤＰ、ADP、ＢＮＮ、ＫＮ、ＬＢＯ、化合物半導体などが好ましい。第二高調波の具体例としては、基本発振波長が860nmの半導体レーザーの場合、その倍波の430nm、また半導体レーザー励起の固体レーザーの場合は、CrドープしたLiSrAlF6結晶（基本発振波長860nm）からの倍波の430nmなどが挙げられる。
上記のようにして得られた本発明の光学記録媒体への記録は、基板の両面または片面に設けた記録層に0.4〜0.6μm程度に集束したレーザー光を照射することにより行う。レーザー光の照射された部分には、レーザー光エネルギーの吸収による、分解、発熱、溶解等の記録層の熱的変形が起こり、光学特性が変化する。
【００３９】
記録された情報の再生は、レーザー光により、光学特性の変化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とることにより行う。
【００４０】
【実施例】
以下本発明を実施例により更に具体的に説明するが、本発明はその要旨を超えない限り、これら実施例によって限定されるものではない。
［化合物の合成法］
７−アミノ置換カルボスチリルの合成法は、今までに複数の合成方法が報告されているが、一般的な製法としては、下記化１０に示すようなｍ−フェニレンジアミン誘導体とβ―ケトエステル誘導体の環化反応を行った後、Ｎアルキル化反応を行う方法が挙げられる（ref. J.O.C.56,3(1991)980、J.Med.Chem.31,7(1988)1347、J.Med.Chem.41,4(1998)623等）。これらの反応は、１，８−ナフチリジンの合成にも適用することができる。
【００４１】
【化１４】
また７−アシルアミノ体の合成法については、例えばアセトアミド体については７−アミノカルボスチリルを無水酢酸中で硫酸存在下撹拌することにより合成できることが報告されている（J.Chem.Eng.data.13,3（1968）440）。
実施例１
【００４３】
【化１５】
上記構造式▲１▼で表される、Ｎ，Ｎ−ジ−ｎ−プロピル−ｍ−フェニレンジアミン２．８８ｇ（０．０１５ｍｏｌ）と、▲２▼で表されるアセト酢酸エチル２．２１ｇ（０．０１７ｍｏｌ）の混合溶液を撹拌しながらオイルバスにより１６０℃で１９ｈ加熱した。
その後、加熱により析出した固体に酢酸エチル１０ｍｌを添加し、１ｈ還流させた後、生成物を濾過した。濾過物は酢酸エチル１０ｍｌ中に懸濁させ、１ｈ室温で撹拌した後に濾過して、濾過物を乾燥させることにより、下記構造式▲３▼で示される生成物１．７７ｇを得ることができた。
【００４５】
【化１６】
次いで、得られた構造式▲３▼で示される化合物０．５１７ｇ（０．００２ｍｏｌ）をＮ，Ｎ−ジメチルホルムアミド１０ｍｌ、水酸化カリウム１．１２ｇ（０．０２ｍｌ）と混合し、この混合液に攪拌下、ヨウ化メチル１．４２ｇ（０．０１ｍｏｌ）を滴下した。滴下終了後、室温で７時間攪拌し、飽和塩化アンモニウム水溶液で中和し、酢酸エチルで抽出した。この酢酸エチル層を濃縮乾固させることにより例示化合物（８５）で示される生成物０．４３ｇを得た。この化合物のクロロホルム中のλmaxは369.0nm、モル吸光係数1.8×104であった。
【００４７】
この化合物をオクタフルオロペンタノールに溶解し、1.0wt%に調整した。これをろ過してできた溶解液を直径120mm、厚さ1.2mmの射出成型ポリカーボネート樹脂基板上に滴下し、スピンコート法により塗布し、塗布後、１００℃で３０分間乾燥した。この塗布膜のλmaxは、379.5nmであった。
実施例２および３
以下、前記の合成法に準じて例示化合物（４８）および（９）の化合物を合成し、膜スペクトルを測定した。
【００４８】
比較例１
実施例１の中間体として得られた、前記構造式▲３▼で示される化合物をオクタフルオロペンタノールに溶解し、1.0wt%に調整した。これをろ過してできた溶解液を直径120mm、厚さ1.2mmの射出成型ポリカーボネート樹脂基板上に滴下し、スピンコート法により塗布し、塗布後、１００℃で３０分間乾燥した。得られた塗布膜は色素の結晶化が見られ、白濁していた。
比較例２
実施例１の方法に準じて下記構造式▲４▼で示される化合物を合成し、比較例１と同様にしてポリカーボネート樹脂基板上に塗布した。得られた塗布膜は色素の結晶化が見られ、白濁していた。
【００４９】
【化１７】
これら実施例１〜３および比較例１、２の化合物の溶液中での最大吸収波長、モル吸光係数、塗布膜での最大吸収波長を合わせて表１に示す。
【表１】
例えばこの塗布膜上に、スパッタリング法等にて銀膜を成膜して反射層を形成し、更に紫外線硬化型樹脂をスピンコート等にて塗布・ＵＶ照射により硬化させて保護層を形成し、光学記録媒体とすることができる。この光学記録媒体は、塗布膜のλmaxの値より、例えば中心波長410nmの半導体レーザーによる記録再生が可能であることが明らかである。
【００５２】
【発明の効果】
本発明化合物の含有溶液は、短波長のレーザー光による記録再生に適した吸収を有する塗布膜を形成することが出来、且つ成膜性にも優れているので、本発明化合物を用いた記録層を有する記録媒体は、短波長レーザーに対応する記録再生用光学記録媒体として有用である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a write-once optical recording medium using an organic dye in a recording layer, and more particularly to a write-once optical recording medium compatible with a blue laser.
[0002]
[Prior art]
In recent years, semiconductor lasers with a short oscillation wavelength have been developed, and there is a demand for optical recording media capable of high-density recording and reproduction using laser light having a wavelength shorter than 780 nm and 830 nm of conventional lasers. . Conventionally proposed optical recording media include magneto-optical recording media, phase change recording media, chalcogen oxide optical recording media, organic dye-based optical recording media, etc. Among these, organic dye-based optical recording media are It is considered to be advantageous in that it is inexpensive in cost and easy in the manufacturing process.
[0003]
Currently, a write-type compact disc (CD-R) of a type in which a metal layer having a high reflectance is laminated on an organic dye layer is mass-produced and widely known as an organic dye-based optical recording medium. A high-density organic dye-based optical recording medium (DVD-R) for recording with a red semiconductor laser having a shorter wavelength than the laser used for recording and reproducing -R has been developed and put into practical use. However, as laser oscillation with shorter wavelengths becomes possible, recording with a laser with a shorter wavelength than DVD-R, that is, a blue semiconductor laser (wavelength 350 nm to 530 nm), aiming for higher density in the future. There is an increasing need for reproducible optical recording media.
[0004]
[Problems to be solved by the invention]
In general, an optical recording medium used as a CD-R or DVD-R has a problem that when recording / reproducing with a blue semiconductor laser having a short wavelength, the reflectance is low and recording / reproducing cannot be performed.
For example, Japanese Patent Application Laid-Open No. 2001-96918 discloses an optical recording medium having a recording layer containing a carbostyryl compound having an amino group at the 7-position. However, according to the study by the present inventors, when the carbostyril compound described in Japanese Patent Application Laid-Open No. 2001-96918 is used as a recording layer, crystallization occurs at the time of film formation and a sufficient reflectance as the recording layer is obtained. I found it impossible. As a result of diligent studies to solve this problem, it was found that a good recording layer free from crystallization can be obtained by using a carbostyryl compound having a specific structure as the recording layer.
An object of the present invention is to provide an organic dye-based optical recording medium that can be recorded and reproduced by a blue semiconductor laser.
[0005]
[Means for Solving the Problems]
The present inventors have result of various investigations on an organic dye having a high sensitivity to a blue semiconductor laser, carbostyril induction body represented by a specific structural formula, used in the recording layer of the optical recording medium corresponding to the blue semiconductor laser It was found out that the present invention was obtained and the present invention was reached.
[0006]
That is, the gist of the present invention is an optical recording medium in which a recording layer capable of recording and / or reproducing information by a laser is provided on a substrate, and the recording layer is represented by the following general formula [I]. It exists in the optical recording medium characterized by containing a carbostyryl compound.
[0007]
[Chemical formula 2]
(Wherein X represents a nitrogen atom or C—R 6 , R 1 represents an alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, aralkyl group, aryl group, saturated or optionally substituted. R 2 and R 4 represent a hydrogen atom, R 5 represents a hydrogen atom except when R 8 and R 5 form a ring, and R 5 represents a group selected from an unsaturated heterocyclic group and an acyl group. 6 is a hydrogen atom except when R 7 and R 6 form a ring R 3 is an alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, alkoxy group, which may have a substituent, Alkylthio group, aralkyl group, alkenyloxy group, aryl group, saturated or unsaturated heterocyclic group, halogen atom, nitro group, cyano group, formyl group, hydroxy group, carboxyl group, sulfonic acid group, A group selected from an amino group, an acylamino group, a carbamate group, a sulfonamide group, a carbamoyl group, a carboxylic acid ester group, a sulfamoyl group, and a sulfonic acid ester group, and R 7 and R 8 each independently have a substituent. Or an alkyl group, an alkenyl group, an aralkyl group, or an acyl group, or R 7 and R 8 are not bonded, and one or more of R 7 and R 6 , and R 8 and R 5 are bonded to form a ring. (It may be formed.)
[0009]
DETAILED DESCRIPTION OF THE INVENTION
The present invention will be described in detail below.
The compound of the above general formula [I] used in the present invention is a dye having an appropriate absorption in the blue light wavelength region of 350 to 530 nm and suitable for recording with blue laser light.
In the general formula (1), R 1 is an optionally substituted alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, aralkyl group, aryl group, saturated or unsaturated heterocyclic group, acyl Although it is a substituent showing the group chosen from a group, the following are illustrated as a preferable substituent among them. A linear or branched alkyl group having 1 to 18 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group and n-heptyl group; cyclopropyl A cycloalkyl group having 3 to 18 carbon atoms such as a group, a cyclopentyl group, a cyclohexyl group and an adamantyl group; a linear or branched alkenyl group having 2 to 18 carbon atoms such as a vinyl group, a propenyl group and a hexenyl group; a cyclopentenyl group; C3-C18 cycloalkenyl group such as cyclohexenyl group; saturated or unsaturated such as 2-thienyl group, 2-pyridyl group, furyl group, thiazolyl group, benzothiazolyl group, morpholino group, pyrrolidinyl group, tetrahydrothiophene dioxide group Saturated heterocyclic group; aryl group having 6 to 18 carbon atoms such as phenyl group, tolyl group, xylyl group, mesityl group; benzyl Aralkyl groups having 7 to 20 carbon atoms such as phenethyl group; linear or branched acyl groups having 2 to 18 carbon atoms such as acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, and isovaleryl group. .
Substituents R 2 and R 4 of the carbostyril compound is a hydrogen atom, R 5 is unless R 8 and R 5 form a ring, a hydrogen atom, R 6 is R 7 and R 6 a ring Except when formed, it is a hydrogen atom.
R 3 represents an optionally substituted alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, alkoxy group, alkylthio group, aralkyl group, alkenyloxy group, aryl group, saturated or unsaturated heterocyclic group. , Halogen atom, nitro group, cyano group, formyl group, hydroxy group, carboxyl group, sulfonic acid group, amino group, acylamino group, carbamate group, sulfonamido group, carbamoyl group, carboxylic acid ester group, sulfamoyl group and sulfonic acid ester It is a group selected from groups. Examples of the substituent represented by R 3 include the following. A linear or branched alkyl group having 1 to 18 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group and n-heptyl group; cyclopropyl A cycloalkyl group having 3 to 18 carbon atoms such as a group, a cyclopentyl group, a cyclohexyl group and an adamantyl group; a linear or branched alkenyl group having 2 to 18 carbon atoms such as a vinyl group, a propenyl group and a hexenyl group; a cyclopentenyl group; C3-C18 cycloalkenyl group such as cyclohexenyl group; saturated or unsaturated such as 2-thienyl group, 2-pyridyl group, furyl group, thiazolyl group, benzothiazolyl group, morpholino group, pyrrolidinyl group, tetrahydrothiophene dioxide group Saturated heterocyclic group; aryl group having 6 to 18 carbon atoms such as phenyl group, tolyl group, xylyl group, mesityl group; benzyl , An aralkyl group having 7 to 20 carbon atoms such as phenethyl; main butoxy group, an ethoxy group, n- propoxy group, isopropoxy group, n- butoxy group, sec- butoxy group, 1 carbon atoms, such as tert- butoxy 18 straight-chain or branched alkoxy groups; C3-C18 straight-chain or branched alkenyloxy groups such as propenyloxy group, butenyloxy group, pentenyloxy group; methylthio group, ethylthio group, n-propylthio group, n- A linear or branched alkylthio group having 1 to 18 carbon atoms such as a butylthio group, a sec-butylthio group or a tert-butylthio group; a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom; a nitro group; a cyano group; a hydroxy group; Formyl group; sulfonic acid group; carboxyl group; -amino group represented by -NR 10 R 11 ; acylamino group represented by -NHCOR 12 ; -NHCOOR 1 A carbamate group represented by 3 ; a sulfonamide group represented by —NHSO 2 R 14 ; a carboxylic acid ester group represented by —COOR 15 ; a carbamoyl group represented by —CONR 16 R 17 ; —SO 2 NR 18 A sulfamoyl group represented by R 19 ; a sulfonic acid ester group represented by —SO 3 R 20 , and the like. R 10 to R 20 are each a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group, an optionally substituted linear, branched or cyclic alkenyl group, an optionally substituted aryl group, or a substituted group. Represents an aralkyl group which may be substituted.
R 3 , R 7 and R 8 are substituents for having an absorption spectrum suitable for recording with a blue laser, and R 7 and R 8 are each independently an alkyl group, alkenyl which may have a substituent. A group, an aralkyl group, or an acyl group, or R 7 and R 8 may not be bonded , and one or more of R 7 and R 6 , and R 8 and R 5 may be bonded to form a ring.
Examples of the alkyl group, alkenyl group, and aralkyl group represented by R 7 and R 8 are the same as those exemplified for R 3 described above . On the other hand, examples of the acyl group include linear or branched acyl groups having 2 to 18 carbon atoms such as an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, and an isovaleryl group. R 7 and R 8 are more preferably a linear or branched alkyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 18 carbon atoms, a linear or branched alkenyl group having 2 to 18 carbon atoms, an acyl group, or R 7 and R 6 or a saturated heterocyclic ring formed by combining R 8 and R 5 . Among these, a linear or branched alkyl group having 1 to 6 carbon atoms is particularly preferable.
[0010]
A plurality of substituents represented by R 3, R 7 and R 8 may be different in the same kind. Also not bind R 7 and R 8, as the case R 7 and R 6, which and one or more R 8 and R 5 are combined to form a ring, fused to the quinoline ring which is a basic skeleton, double prime ring, some have the R 7 and R 6, and julolidine ring, and in which one or more R 8 and R 5 is formed by bond. These rings may further have a substituent.
[0013]
The alkyl group, alkenyl group, aryl group and heterocyclic group contained in the group represented by R 1 to R 20 (excluding R 2 , R 4 , R 5 and R 6 ) may be further substituted. . In this case, examples of the substituent include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group and the like, an alkoxy group having 1 to 10 carbon atoms; Group, ethoxymethoxy group, propoxymethoxy group, ethoxyethoxy group, propoxyethoxy group, methoxybutoxy group, etc., alkoxyalkoxy group having 2 to 12 carbon atoms; methoxymethoxymethoxy group, methoxymethoxyethoxy group, methoxyethoxymethoxy group, methoxymethoxy An alkoxyalkoxyalkoxy group having 3 to 15 carbon atoms such as ethoxy group and ethoxyethoxymethoxy group; an aryloxy group; an aryl group having 6 to 12 carbon atoms such as phenyl group, tolyl group and xylyl group (these are further substituted with a substituent) Phenoxy group, tolyluo Aryloxy groups having 6 to 12 carbon atoms such as xyl group, xylyloxy group and naphthyloxy group; alkenyloxy groups having 2 to 12 carbon atoms such as allyloxy group and vinyloxy group; acyl groups such as acetyl group and propionyl group; cyano group A nitro group; a hydroxyl group; a tetrahydrofuryl group; an amino group; an alkylamino group having 1 to 10 carbon atoms such as an N, N-dimethylamino group and an N, N-diethylamino group; a methylsulfonylamino group, an ethylsulfonylamino group; C1-C6 alkylsulfonylamino groups such as n-propylsulfonylamino group; halogen atoms such as fluorine atom, chlorine atom and bromine atom; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group Alkoxyalkoxy having 2 to 7 carbon atoms such as n-butoxycarbonyl Bonyl group; C2-C7 alkylcarbonyloxy group such as methylcarbonyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, isopropylcarbonyloxy group, n-butylcarbonyloxy group; methoxycarbonyloxy group, ethoxy Examples thereof include C2-C7 alkoxycarbonyloxy groups such as carbonyloxy group, n-propoxycarbonyloxy group, isopropoxycarbonyloxy group, n-butoxycarbonyloxy group and the like.
[0017]
The molecular weight of the compound represented by the general formula [I] is preferably 2,000 or less, more preferably 1,000 or less. Specific examples of the compound represented by the general formula [I] include the following, but are not limited thereto.
[0018]
[Chemical formula 2]
[Chemical 3]
[Formula 4]
[Chemical formula 5]
[Chemical 6]
[Chemical 7]
These dyes of the present invention are extremely useful as dyes for use in the recording layer of optical recording media because they are excellent in thin film formation when forming a recording layer from a solution containing the dye, for example. In addition, the dye of the present invention has a recording layer containing the dye having an absorption intensity suitable for recording / reproduction with a laser beam in a shorter wavelength (350 nm to 530 nm) region. It is extremely useful as a dye for use in an optical recording medium for reproduction.
[0029]
The optical recording medium of the present invention is basically composed of a substrate and a recording layer containing the compound, and further, if necessary, an undercoat layer, a metal reflective layer, a protective layer, etc. on the substrate. It may be provided.
As an example of a preferred layer structure, a recording layer is provided on a substrate, and a high reflectance medium in which a metallic reflective layer such as gold, silver, and aluminum and a protective layer are further provided on the recording layer, gold on the substrate, Examples thereof include a highly reflective medium in which a metal reflective layer such as silver or aluminum is provided and a protective layer is further provided on the metal reflective layer.
[0030]
Hereinafter, the optical recording medium of the present invention will be described using the medium having this structure as an example.
The material of the substrate in the optical recording medium of the present invention may be basically transparent at the wavelength of recording light and reproducing light.
Examples of such materials include acrylic resins, methacrylic resins, polycarbonate resins, polyolefin resins (particularly amorphous polyolefins), polyester resins, polystyrene resins, epoxy resins, and the like, and glass materials. A glass having a resin layer made of a radiation curable resin such as a photocurable resin can be used.
[0031]
From the viewpoints of high productivity, cost, moisture absorption resistance, etc., injection molded polycarbonate is preferred.
Amorphous polyolefin is preferred from the standpoint of chemical resistance and moisture absorption resistance.
Moreover, a glass substrate is preferable from the viewpoint of high-speed response.
A resin substrate or a resin layer may be provided in contact with the recording layer, and guide grooves or pits for recording / reproducing light may be provided on the resin substrate or resin layer. When the guide groove is spiral, the groove pitch is preferably about 0.2 to 1.2 μm.
A recording layer containing the compound of the present invention is formed on a substrate or, if necessary, an undercoat layer or the like.
[0032]
As a method for forming the recording layer, a generally used thin film forming method such as a vacuum deposition method, a sputtering method, a doctor blade method, a casting method, a spin coating method, or an immersion method can be given. The spin coating method is preferable from the viewpoint of mass productivity and cost. Further, from the viewpoint that a recording layer having a uniform thickness can be obtained, a vacuum deposition method or the like is preferable to a coating method.
[0033]
In the case of film formation by a spin coating method, the number of rotations is preferably 500 to 15000 rpm, and after spin coating, a treatment such as heating or solvent vapor may be performed in some cases.
The coating solvent for forming the recording layer by a coating method such as a doctor blade method, a casting method, a spin coating method, or a dipping method may be any solvent that does not attack the substrate and is not particularly limited. For example, ketone alcohol solvents such as diacetone alcohol and 3-hydroxy-3-methyl-2-butanone; cellosolv solvents such as methyl cellosolve and ethyl cellosolve; chain hydrocarbon solvents such as n-hexane and n-octane Cyclic hydrocarbon solvents such as cyclohexane, methylcyclohexane, ethylcyclohexane, dimethylcyclohexane, n-butylcyclohexane, tert-butylcyclohexane and cyclooctane; perfluoroalkyl alcohols such as tetrafluoropropanol, octafluoropentanol and hexafluorobutanol Examples of the solvent include hydroxycarboxylic acid ester solvents such as methyl lactate, ethyl lactate, and methyl isobutyrate.
[0034]
In the case of the vacuum deposition method, for example, the compound of the present invention and, if necessary, recording layer components such as other dyes and various additives are put in a crucible installed in the vacuum vessel, and the inside of the vacuum vessel is appropriately vacuumed. After evacuating to about 10 −2 to 10 −5 Pa with a pump, the crucible is heated to evaporate the components of the recording layer, and vapor deposited on a substrate placed facing the crucible to form a recording layer.
In addition, the recording layer has a transition metal chelate compound (for example, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-α-diketone, etc.) as a singlet oxygen quencher to improve the stability and light resistance of the recording layer. ) And the like, and a recording sensitivity improver such as a metal compound may be contained for improving the recording sensitivity. Here, the metal compound refers to a compound in which a metal such as a transition metal is contained in the compound in the form of atoms, ions, clusters, etc., for example, an ethylenediamine complex, an azomethine complex, a phenylhydroxyamine complex, a phenanthroline complex, Organic metal compounds such as dihydroxyazobenzene complex, dioxime complex, nitrosoaminophenol complex, pyridyltriazine complex, acetylacetonate complex, metallocene complex and porphyrin complex can be mentioned. Although it does not specifically limit as a metal atom, It is preferable that it is a transition metal.
Furthermore, other types of pigments can be used in combination as necessary. Other dyes are not particularly limited as long as they have appropriate absorption mainly in the laser wavelength region for recording. In addition, multiple dyes suitable for recording with a near-infrared laser of a wavelength selected from 770 to 830 nm such as CD-R and a red laser selected from 620 to 690 nm such as DVD-R are used in combination. An optical recording medium corresponding to recording with a laser beam in a wavelength region may be used.
Other dyes include metal-containing azo dyes, phthalocyanine dyes, naphthalocyanine dyes, cyanine dyes, azo dyes, squarylium dyes, metal-containing indoaniline dyes, triarylmethane dyes, merocyanine dyes, Examples include azulenium dyes, naphthoquinone dyes, anthraquinone dyes, indophenol dyes, xanthene dyes, oxazine dyes, and pyrylium dyes.
Furthermore, a binder, a leveling agent, an antifoaming agent, etc. can also be used together as needed. Preferable binders include polyvinyl alcohol, polyvinyl pyrrolidone, nitrocellulose, cellulose acetate, ketone resin, acrylic resin, polystyrene resin, urethane resin, polyvinyl butyral, polycarbonate, polyolefin and the like.
[0035]
The film thickness of the recording layer varies depending on the recording method and the like, and is not particularly limited, but is usually 50 to 300 nm.
A reflective layer may be formed on the recording layer, and the thickness thereof is preferably 50 to 300 nm. As a material of the reflective layer, a material having a sufficiently high reflectivity at the wavelength of the reproduction light, for example, Au, Al, Ag, Cu, Ti, Cr, Ni, Pt, Ta, Cr, and Pd metal alone or in an alloy It is possible to use. Among these, Au, Al, and Ag have high reflectivity and are suitable as a material for the reflective layer. In addition to these as main components, the following may be included. For example, Mg, Se, Hf, V, Nb, Ru, W, Mn, Re, Fe, Co, Rh, Ir, Cu, Zn, Cd, Ga, In, Si, Ge, Te, Pb, Po, Sn, Mention may be made of metals such as Bi and metalloids. Among these, those containing Ag as a main component are particularly preferred because of low cost, high reflectivity, and when a print receiving layer described later is provided, a white and beautiful ground color can be obtained. Here, the main component means one having a content of 50% or more.
It is also possible to form a multilayer film by alternately stacking a low refractive index thin film and a high refractive index thin film using a material other than metal, and use it as a reflective layer.
[0036]
Examples of the method for forming the reflective layer include sputtering, ion plating, chemical vapor deposition, and vacuum vapor deposition. In addition, a known inorganic or organic intermediate layer or adhesive layer may be provided on the substrate or below the reflective layer in order to improve reflectivity, improve recording characteristics, and improve adhesion.
The material for the protective layer formed on the reflective layer is not particularly limited as long as it protects the reflective layer from external force. Examples of the organic material include thermoplastic resins, thermosetting resins, electron beam curable resins, and UV curable resins. Examples of inorganic substances include SiO 2 , Si 3 N 4 , MgF 2 , SnO 2 and the like.
A thermoplastic resin, a thermosetting resin, or the like can be formed by dissolving in an appropriate solvent, applying a coating solution, and drying. The UV curable resin can be formed by preparing a coating solution as it is or by dissolving it in a suitable solvent, and then applying the coating solution and curing it by irradiating with UV light. As the UV curable resin, for example, acrylate resins such as urethane acrylate, epoxy acrylate, and polyester acrylate can be used. These materials may be used alone or in combination, and may be used not only as a single layer but also as a multilayer film.
As a method for forming the protective layer, a coating method such as a spin coating method and a casting method, a sputtering method, a chemical vapor deposition method, and the like are used as in the recording layer. Among these, a spin coating method is preferable.
[0037]
The thickness of the protective layer is generally in the range of 0.1 to 100 μm, but in the present invention, 3 to 30 μm is preferable.
The above description has been made with reference to an example of an optical recording medium having a basic layer structure in which a substrate / recording layer / reflective layer / protective layer are stacked in this order and performing recording / reproduction with laser light irradiated through the substrate. As long as the characteristics of the present invention are not impaired, an arbitrary layer may be provided between these layers.
Further, the substrate may be further bonded to the protective layer or the reflective layer without providing the protective layer via an adhesive layer or the like. The substrate may be the substrate itself without any layers, or may have an arbitrary layer on the bonding surface or the opposite surface. An optical recording medium capable of double-sided recording / reproduction may be provided by making the protective layer and / or the reflective layer face each other and two substrates having at least the recording layer face each other.
By the way, as one means for increasing the recording density of the optical recording medium, it has been proposed to increase the numerical aperture of the objective lens to reduce the light spot focused on the information recording surface. When the numerical aperture is increased, the aberration of the light spot that is collected increases due to the influence of the warp of the disk, and there is a problem that a good recording / reproducing signal cannot be stably obtained.
In order to reduce the aberration generated by the warp of the medium, for example, the thickness of the transparent substrate through which the recording / reproducing laser beam passes is reduced to about 0.1 mm, or the substrate / reflection layer / recording is performed. It is preferable that recording / reproduction is performed through a protective layer on an optical recording medium in which layers / protective films are sequentially laminated. This protective film may be a film or a sheet-like material bonded together with an adhesive, or may be formed by applying a film-forming coating solution in the same manner as the protective layer described above. Any layer may be provided between each of the above layers as long as the characteristics of the present invention are not impaired.
In any of the above-described stacked media, if necessary, the surface that is not the recording / reproducing light incident surface can be filled (printed) with various printers such as inkjet and thermal transfer, or various writing tools. A layer may be provided.
The laser beam used for the optical recording medium of the present invention is preferably as short as possible for high-density recording, but a laser beam of 350 to 530 nm is particularly preferable. Typical examples of such laser light include laser light having center wavelengths of 405 nm, 410 nm, and 515 nm.
[0038]
An example of laser light having a wavelength in the range of 350 to 530 nm can be obtained by using a high-power semiconductor laser of 405 nm, 410 nm blue or 515 nm blue-green, but, for example, (a) the fundamental oscillation wavelength is Either a semiconductor laser capable of continuous oscillation of 740 to 960 nm, or (b) a solid laser capable of continuous oscillation excited by a semiconductor laser and having a fundamental oscillation wavelength of 740 to 960 nm is generated by a second harmonic generation element (SHG). It can also be obtained by wavelength conversion.
The SHG may be any piezoelectric element that lacks inversion symmetry, but KDP, ADP, BNN, KN, LBO, a compound semiconductor, and the like are preferable. As a specific example of the second harmonic, in the case of a semiconductor laser having a fundamental oscillation wavelength of 860 nm, 430 nm of its harmonic wave, and in the case of a solid-state laser pumped by a semiconductor laser, a Cr-doped LiSrAlF 6 crystal (fundamental oscillation wavelength of 860 nm) 430nm of the double wave from.
Recording on the optical recording medium of the present invention obtained as described above is performed by irradiating the recording layer provided on both sides or one side of the substrate with laser light focused to about 0.4 to 0.6 μm. In the portion irradiated with the laser beam, thermal deformation of the recording layer such as decomposition, heat generation and dissolution due to absorption of laser beam energy occurs, and the optical characteristics change.
[0039]
Reproduction of recorded information is performed by reading the difference in reflectance between the portion where the change in optical characteristics has occurred and the portion where the change has not occurred, with laser light.
[0040]
【Example】
EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples unless it exceeds the gist.
[Synthesis of compounds]
As a method for synthesizing 7-amino-substituted carbostyril, a plurality of synthetic methods have been reported so far. As a general production method, m-phenylenediamine derivatives and β-ketoester derivatives as shown in the following chemical formula 10 can be used. Examples include a method in which an N alkylation reaction is performed after the cyclization reaction (ref. JOC56, 3 (1991) 980, J. Med. Chem. 31, 7 (1988) 1347, J. Med. Chem. 41 , 4 (1998) 623 etc.). These reactions can also be applied to the synthesis of 1,8-naphthyridine.
[0041]
Embedded image
As for the method for synthesizing the 7-acylamino compound, for example, it has been reported that the acetamide compound can be synthesized by stirring 7-aminocarbostyril in acetic anhydride in the presence of sulfuric acid (J. Chem. Eng. Data. 13). , 3 (1968) 440).
Example 1
[0043]
Embedded image
2.88 g (0.015 mol) of N, N-di-n-propyl-m-phenylenediamine represented by the above structural formula (1) and 2.21 g (0 of ethyl acetoacetate represented by (2) .017 mol) was heated in an oil bath at 160 ° C. for 19 hours while stirring.
Thereafter, 10 ml of ethyl acetate was added to the solid precipitated by heating and refluxed for 1 h, and then the product was filtered. The filtrate was suspended in 10 ml of ethyl acetate, stirred for 1 h at room temperature, filtered, and dried to obtain 1.77 g of a product represented by the following structural formula (3). .
[0045]
Embedded image
Next, 0.517 g (0.002 mol) of the compound represented by the structural formula (3) thus obtained was mixed with 10 ml of N, N-dimethylformamide and 1.12 g (0.02 ml) of potassium hydroxide. Under stirring, 1.42 g (0.01 mol) of methyl iodide was added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature for 7 hours, neutralized with a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer was concentrated to dryness to obtain 0.43 g of the product represented by the exemplified compound (85). Λmax of this compound in chloroform was 369.0 nm, and the molar extinction coefficient was 1.8 × 10 4 .
[0047]
This compound was dissolved in octafluoropentanol and adjusted to 1.0 wt%. A solution obtained by filtering this was dropped onto an injection-molded polycarbonate resin substrate having a diameter of 120 mm and a thickness of 1.2 mm, applied by spin coating, and dried at 100 ° C. for 30 minutes. The coating film had a λmax of 379.5 nm.
Examples 2 and 3
Hereinafter, the compounds of Exemplified compounds (48) and (9) were synthesized according to the synthesis method described above, and the film spectrum was measured.
[0048]
Comparative Example 1
The compound represented by the structural formula (3) obtained as an intermediate of Example 1 was dissolved in octafluoropentanol and adjusted to 1.0 wt%. A solution obtained by filtering this was dropped onto an injection-molded polycarbonate resin substrate having a diameter of 120 mm and a thickness of 1.2 mm, applied by spin coating, and dried at 100 ° C. for 30 minutes. The obtained coating film had crystallization of pigments and was cloudy.
Comparative Example 2
According to the method of Example 1, a compound represented by the following structural formula (4) was synthesized and applied onto a polycarbonate resin substrate in the same manner as in Comparative Example 1. The obtained coating film had crystallization of pigments and was cloudy.
[0049]
Embedded image
Table 1 shows the maximum absorption wavelength, molar extinction coefficient, and maximum absorption wavelength in the coating film of the compounds of Examples 1 to 3 and Comparative Examples 1 and 2 together.
[Table 1]
For example, on this coating film, a silver film is formed by sputtering or the like to form a reflective layer, and further a UV curable resin is applied by spin coating or the like and cured by UV irradiation to form a protective layer. It can be an optical recording medium. From the value of λmax of the coating film, it is clear that this optical recording medium can be recorded and reproduced by a semiconductor laser having a central wavelength of 410 nm, for example.
[0052]
【The invention's effect】
The solution containing the compound of the present invention can form a coating film having an absorption suitable for recording / reproduction with a laser beam with a short wavelength, and is excellent in film formability. Therefore, a recording layer using the compound of the present invention Is useful as an optical recording medium for recording and reproduction corresponding to a short wavelength laser.
Claims (1)
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| JP2001322562A JP4178783B2 (en) | 2001-10-19 | 2001-10-19 | Optical recording medium |
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| JP2001322562A JP4178783B2 (en) | 2001-10-19 | 2001-10-19 | Optical recording medium |
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| JP2003127542A JP2003127542A (en) | 2003-05-08 |
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| US7235551B2 (en) | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
| BR0114829A (en) | 2000-10-23 | 2003-09-23 | Smithkline Beecham Corp | New compounds |
| CA2515939A1 (en) | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Novel compounds |
| CN100509426C (en) * | 2004-02-26 | 2009-07-08 | 三菱化学株式会社 | Optical recording material and optical recording medium |
| TW200724142A (en) | 2005-03-25 | 2007-07-01 | Glaxo Group Ltd | Novel compounds |
| US7423042B2 (en) | 2005-03-25 | 2008-09-09 | Glaxo Group Limited | Compounds |
| WO2006104917A2 (en) | 2005-03-25 | 2006-10-05 | Glaxo Group Limited | Process for preparing pyrido[2,3-d]pyrimidin-7-one and 3,4-dihydropyrimido[4,5-d]pyrimidin-2(1h)-one derivatives |
| TWI389690B (en) | 2005-03-25 | 2013-03-21 | Glaxo Group Ltd | Novel compounds |
| EP2214662B1 (en) | 2007-10-22 | 2016-07-13 | Sunesis Pharmaceuticals, Inc. | (+)-1,4-dihydro-7-[(3s,4s)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid in combination with gemcitabine for use in treating cancer |
| UA108194C2 (en) | 2008-12-31 | 2015-04-10 | METHOD OF OBTAINING (+) - 1,4-DIGIDRO-7 - [(3S, 4S) -3-METOXY-4- (METHYLAMINO) -1-PYROLIDINYL] -4-OXO-1- (2-THIAZOLYL) -1, 8-NAFTYRIDINE-3-CARBOXYLIC ACID | |
| UA110465C2 (en) | 2009-09-04 | 2016-01-12 | Sunesis Pharmaceutecals Inc | Stable sns-595 composition |
| WO2011056566A2 (en) | 2009-10-26 | 2011-05-12 | Sunesis Pharmaceuticals, Inc. | Compounds and methods for treatment of cancer |
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