JP4119099B2 - Optical recording medium - Google Patents
Optical recording medium Download PDFInfo
- Publication number
- JP4119099B2 JP4119099B2 JP2001079723A JP2001079723A JP4119099B2 JP 4119099 B2 JP4119099 B2 JP 4119099B2 JP 2001079723 A JP2001079723 A JP 2001079723A JP 2001079723 A JP2001079723 A JP 2001079723A JP 4119099 B2 JP4119099 B2 JP 4119099B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- recording medium
- atom
- optical recording
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 229910052752 metalloid Inorganic materials 0.000 description 1
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- 229920005668 polycarbonate resin Polymers 0.000 description 1
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- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
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- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
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- 238000004528 spin coating Methods 0.000 description 1
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- 239000011115 styrene butadiene Substances 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(II) oxide Inorganic materials [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
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- 239000001018 xanthene dye Substances 0.000 description 1
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- Optical Record Carriers And Manufacture Thereof (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、データ用大容量追記型光記録媒体（大容量追記型コンパクトディスク、ＤＶＤ−Ｒ）に関するものである。本発明に係るデータ用大容量追記型光記録媒体は、大容量光カードに応用することもできる。
【０００２】
【従来の技術】
現在、次世代大容量光ディスクとしてＤＶＤ−Ｒの開発が進められている。記録容量を向上させるための要素技術には、記録ピット微少化のための記録材料の開発、ＭＰＥＧ２に代表される画像圧縮技術の採用、記録ピット読み取りのための半導体レーザの短波長化等の技術開発が必要である。
【０００３】
これまで赤色波長域の半導体レーザとしては、バーコードリーダ、計測器用に６７０ｎｍ帯のＡｌＧａＩｎＰレーザダイオードが商品化されているのみであったが、光ディスクの高密度化に伴い、赤色レーザが本格的に光ストレージ市場で使用されつつある。ＤＶＤドライブの場合、光源として６３５ｎｍ帯と６５０ｎｍ帯のレーザダイオードの２つの波長で規格化されている。高密度記録のためには、波長はより短波長化が望ましく、追記メディア用ドライブとしては波長６３５ｎｍが好ましい。一方、再生専用のＤＶＤ−ＲＯＭドライブは波長〜６５０ｎｍで商品化されている。
【０００４】
このような状況下で特に好ましいＤＶＤ−Ｒメディアは、波長〜６３５ｎｍで記録、再生が可能でかつ波長〜６５０ｎｍでも再生が可能なメディアである。しかしながら、耐光性、保存安定性に優れ、６５０ｎｍ以下のレーザを用いた光ピックアップで記録、再生が可能な記録材料は未だに開発されていない。
【０００５】
追記型光記録媒体（ＷＯＲＭ）（情報記録用）の従来技術としては、シアニン色素を記録材料として用いたもの（例えば、特開昭５７−８２０９３など）、フタロシアニン色素を記録材料として用いたもの（例えば、特開昭６１−１５０２４３など）などが挙げられる。また、追記型コンパクトディスク（ＣＤ−Ｒ）の従来技術としては、シアニン色素＋金属反射層を記録材料としたもの（例えば、特開平１−１５９８４２など）、フタロシアニン色素＋金属反射層を記録材としたもの（例えば、特開平１−１７６５８５など）、アゾ金属キレート色素＋金属反射層を記録材料としたもの（例えば、特開平４−４６１８６など）などが挙げられる。
【０００６】
更に、大容量追記型コンパクトディスク（ＤＶＤ−Ｒ）の従来技術としては、例えば、イミダゾール系アゾメチン色素＋金属反射層を記録材料としたもの（例えば、特開平８−１９８８７２、同８−２０９０１２、同８−２８３２６３など）などが挙げられる。
【０００７】
本発明者らは、各種色素化合物を鋭意検討した結果、特定の構造を有する色素を主成分とする記録層とすることにより、発振波長７００ｎｍ以下の半導体レーザを用いる次世代大容量光ディスクシステムに適用が可能であることを見出した。
【０００８】
また、本発明者らは、記録材料の構造の一部を限定することにより、溶解度を向上させること、熱特性を制御すること、金属錯体安定性を向上させることができ、扱いやすく、高密度記録可能で、高耐光性である光記録媒体を提供できることを見出した。
【０００９】
【発明が解決しようとする課題】
そこで、本発明は、従来システムに比べて、短波長に発振波長を有する半導体レーザを用いるＤＶＤ−Ｒディスクシステムに適用可能な耐光性、保存安定性に優れた記録材料からなる記録層を有する光記録媒体を提供することをその課題とする。
【００１０】
【課題を解決するための手段】
本発明によれば、上記課題を解決するため、下記の光記録媒体が提供される。
（１）基板上に記録層を設けてなる光記録媒体において、下記一般式（Ｉ）：
【化８】
Ｒ1〜Ｒ3は、それぞれ独立して、水素原子、ハロゲン原子、置換もしくは未置換のアルキル基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアリール基、アミノ基、置換もしくは未置換のアルキルアミノ基又は置換もしくは未置換のジアルキルアミノ基を表す。）、又は一般式（II）：
【化９】
Ｒ1〜Ｒ3は、それぞれ前記と同じ意味を有する。）、又は一般式（III）：
【化１０】
Ｒ4及びＲ5は、それぞれ独立して、水素原子、置換もしくは未置換のアルキル基又は置換もしくは未置換のアリール基を意味し、置換もしくは未置換のアルキル基である場合には、結合して冠状になっていてもよい。）
で示されるアゾ化合物と、金属、金属酸化物又はその塩からなるアゾ金属キレート化合物を少なくとも一種類を記録層中に含有することを特徴とする光記録媒体。
（２）上記（１）に記載の光記録媒体おいて、上記アゾ化合物が、下記一般式（IV）：
【化１１】
Ｒ1〜Ｒ3は前記と同じ意味を有する。）
で表される複素環化合物であることを特徴とする光記録媒体。
（３）上記（１）又は（２）に記載の光記録媒体において、前記アゾ化合物が、下記一般式（Ｖ）：
【化１２】
Ｐは、ヘテロ原子を含んでいてもよい縮合環構造を表し、
Ｙｎは、複素環に直接結合している整数ｎ個の置換基を表す（ｎ＝０の場合は置換基を有していないことを表す）
で表される複素環化合物であることを特徴とする光記録媒体。
（４）上記（１）に記載の光記録媒体おいて、上記アゾ化合物が、下記一般式（VI）：
【化１３】
（５）上記（１）に記載の光記録媒体おいて、上記アゾ化合物が、下記一般式（VII）：
【化１４】
で表される複素環化合物であることを特徴とする光記録媒体。
（６）上記（１）〜（５）のいずれか一項に記載の光記録媒体において、前記アゾ金属キレート化合物の金属又は金属酸化物が２価又は３価であることを特徴とする光記録媒体。
（７）上記（１）〜（６）のいずれか一項に記載の光記録媒体において、前記アゾ金属キレート化合物の金属原子がコバルト、ニッケル、銅又はマンガンであることを特徴とする光記録媒体。
（８）上記（１）〜（７）のいずれか一項に記載の光記録媒体において、記録再生波長±５ｎｍの波長領域の光に対する記録層単層の屈折率ｎが１．５≦ｎ≦３．０であり、消衰係数ｋが０．０２≦ｋ≦０．２０である光記録媒体。
（９）上記（１）〜（８）のいずれか一項に記載の光記録媒体において、下記（イ）、（ロ）又は（ハ）の性質を有することを特徴とする光記録媒体。
（イ）記録層が波長６００ｎｍ〜７００ｎｍのレーザ光により光学的な変化を生じるものであること。
（ロ）有機色素の熱重量分析で、主減量過程での温度に対する減量の傾きが２％／℃以上であること。
（ハ）有機色素の熱重量分析で、主減量過程での総減量が２５％以上であること。
（１０）上記（１）〜（９）のいずれか一項に記載の光記録媒体において、基板上のトラックピッチが０．７〜０．８μｍであり、溝幅が半値幅で０．２０〜０．３６μｍであることを特徴とする光記録媒体。
【００１１】
【発明の実施の形態】
以下本発明について詳細に説明する。
本発明の第１の形態において使用することができる新規アゾ化合物は、一般式（Ｉ）：
【化１５】
Ｒ1〜Ｒ3は、それぞれ独立して、水素原子、ハロゲン原子、置換もしくは未置換のアルキル基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアリール基、アミノ基、置換もしくは未置換のアルキルアミノ基又は置換もしくは未置換のジアルキルアミノ基を表す。）
で表される複素環化合物である。
【００１２】
上記一般式（Ｉ）で表されるアゾ化合物において、好ましい化合物としては、一般式（IV）：
【化１６】
Ｒ1〜Ｒ3は前記と同じ意味を有する。）
で表される複素環化合物が挙げられる。
【００１３】
上記一般式（Ｉ）で表されるアゾ化合物において、好ましい化合物としては、一般式（Ｖ）：
【化１７】
Ｐは、ヘテロ原子を含んでもよい縮合環構造を表し、
Ｙは、複素環に直接結合している整数ｎ個の置換基を表す（ｎ＝０の場合は置換基を有していないことを表す））
で表される複素環化合物が挙げられる。
【００１４】
本発明の第２の形態において使用することができる新規アゾ化合物は、一般式（II）：
【化１８】
Ｒ1〜Ｒ3は、それぞれ前記と同じ意味を有する。）
で表される複素環化合物である。
【００１５】
本発明の第２の形態における好ましい実施態様としては、上記アゾ化合物が、下記一般式（VI）：
【化１９】
で表される複素環化合物が挙げられる。
【００１６】
本発明の第３の形態において使用することができる新規アゾ化合物は、一般式（III）：
【化２０】
Ｒ4及びＲ5は、それぞれ独立して、水素原子、置換もしくは未置換のアルキル基又は置換もしくは未置換のアリール基を意味する。）
で表される複素環化合物が挙げられる。
【００１７】
本発明の第３の形態における好ましい実施態様としては、上記アゾ化合物が、下記一般式（VII）：
【化２１】
で表される複素環化合物が挙げられる。
【００１８】
上記一般式において、ハロゲン原子としては、フッ素、塩素、臭素又はヨウ素が挙げられる。
上記一般式において、アルキル基は、一価の直鎖状、分岐鎖状もしくは環状の脂肪族炭化水素水素残基を意味し、かかるアルキル基の例としては、例えば、メチル基、エチル基、ｎ−プロピル基、ｎ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプチル基、ｎ−オクチル基、ｎ−ノニル基、ｎ−デシル基等の一級アルキル基、イソブチル基、イソアミル基、２−メチルブチル基、２−メチルペンチル基、３−メチルペンチル基、４−メチルペンチル基、２−エチルブチル基、２−メチルヘキシル基、３−メチルヘキシル基、４−メチルヘキシル基、５−メチルヘキシル基、２−エチルペンチル基、３−エチルペンチル基、２−メチルヘプチル基、３−メチルヘプチル基、４−メチルヘプチル基、５−メチルヘプチル基、２−エチルヘキシル基、３−エチルヘキシル基、イソプロピル基、ｓｅｃ−ブチル基、１−エチルプロピル基、１−メチルブチル基、１，２−ジメチルプロピル基、１−メチルヘプチル基、１−エチルブチル基、１，３−ジメチルブチル基、１，２−ジメチルブチル基、１−エチル−２−メチルプロピル基、１−メチルヘキシル基、１−エチルヘプチル基、１−プロピルブチル基、１−イソプロピル−２−メチルプロピル基、１−エチル−２−メチルブチル基、１−エチル−２−メチルブチル基、１−プロピル−２−メチルプロピル基、１−メチルヘプチル基、１−エチルヘキシル基、１−プロピルペンチル基、１−イソプロピルペンチル基、１−イソプロピル−２−メチルブチル基、１−イソプロピル−３−メチルブチル基、１−メチルオクチル基、１−エチルヘプチル基、１−プロピルヘキシル基、１−イソブチル−３−メチルブチル基等の二級アルキル基、ネオペンチル基、ｔｅｒｔ−ブチル基、ｔｅｒｔ−ヘキシル基、ｔｅｒｔ−アミル基、ｔｅｒｔ−オクチル基等の三級アルキル基、シクロヘキシル基、４−メチルシクロヘキシル基、４−エチルシクロヘキシル基、４−ｔｅｒｔ−ブチルシクロヘキシル基、４−（２−エチルヘキシル）シクロヘキシル基、ボルニル基、イソボルニル基（アダマンタン基）等のシクロアルキル基等が挙げられる。更に、これら一級及び二級アルキル基は、例えば、水酸基、ハロゲン原子、ニトロ基、カルボキシ基、シアノ基、置換もしくは未置換のアリール基、置換もしくは未置換の複素環残基等によって置換されていてもよく、また酸素、硫黄、窒素等の原子を介して上記アルキル基で置換されていてもよい。
【００１９】
更に、酸素を介して置換されているアルキル基としては、例えば、メトキシメチル基、メトキシエチル基、エトキシメチル基、エトキシエチル基、ブトキシエチル基、エトキシエトキシエチル基、フェノキシエチル基、メトキシプロピル基、エトキシプロピル基、ピペリジノ基、モルホリノ基等が挙げられ、硫黄を介して置換されているアルキル基としては、例えば、メチルチオエチル基、エチルチオエチル基、エチルチオプロピル基、フェニルチオエチル基等が挙げられ、窒素を介して置換されているアルキル基としては、例えば、ジメチルアミノエチル基、ジエチルアミノエチル基、ジエチルアミノプロピル基等が挙げられる。
【００２０】
上記一般式において、アルコキシ基は、酸素原子に置換もしくは未置換のアルキル基が直接結合されているものであればよく、かかるアルキル基の具体例としては、前述の具体例を挙げることができる。
【００２１】
上記一般式において、アリールオキシ基は、酸素原子に置換もしくは未置換のアリール基が直接結合されているものであればよく、かかるアリール基の具体例としては、例えば、フェニル基、ペンタレニル基、インデニル基、ナフチル基、アズレニル基、ヘプタレニル基、ビフェニレニル基、フェナレニル基、フェナントレニル基、アントラセニル基、トリフェニレニル基、ピレニル基等が挙げられる。
【００２２】
上記一般式において、アルコキシカルボニル基は、アルコキシカルボニル基の酸素原子に置換もしくは未置換のアルキル基が直接結合されているものであればよく、かかるアルキル基の具体例としては前述の具体例を挙げることができる。
【００２３】
上記一般式において、アリールオキシカルボニル基としては、アリールオキシカルボニル基の酸素原子に置換もしくは未置換のアリール基が直接結合されているものであればよく、かかるアリール基の具体例としては前述の具体例を挙げることができる。
【００２４】
上記一般式において、カルバモイル基は、カルバモイル基の窒素原子にそれぞれ独立して水素原子、置換もしくは未置換のアルキル基又は置換もしくは未置換のアリール基が直接結合されているものであればよく、かかるアルキル基及びアリール基の具体例としては前述の具体例を挙げることができる。
【００２５】
上記一般式において、アシル基は、アシル基のカルボニル炭素原子に置換もしくは未置換のアルキル基又は置換もしくは未置換のアリール基が直接結合されているものであればよく、アルキル基及びアリール基の具体例としては前述の具体例を挙げることができる。
【００２６】
上記一般式において、アミノ基は、窒素原子に置換もしくは未置換のアルキル基又は置換もしくは未置換のアリール基が直接結合されているものであればよく、かかるアルキル基及びアリール基の具体例としては前述の具体例を挙げることができる。
【００２７】
上記一般式において、複素環残基の具体例としては、例えば、インドリル基、フリル基、チエニル基、ピリジル基、ピペリジル基、キノリル基、イソキノリル基、ピペリジノ基、モルホリノ基、ピロリル基等が挙げられる。
【００２８】
上記一般式において、Ｒ1とＲ2が連結して環を形成したアミノ基の具体例は、ピペリジノ基、モルホリノ基、ピロリジル基、ピペラジル基、イミダゾリジル基、ピラゾリジル基、インドリニル基、イソインドリニル基、ピロリル基、インドリル基、イソインドリル基、カルバゾリル基等が挙げられる。
【００２９】
上記一般式において、２価もしくは３価の金属原子の具体例は、例えば、チタン、バナジウム、クロム、マンガン、鉄、コバルト、ニッケル、銅、ジリコニウム、ニオブ、モリブデン、テクネニウム、ルテニウム、ロジウム、パラジウム等が挙げられ、金属酸化物の具体例は酸化バナジウム等が挙げられ、特に、コバルト、ニッケル、銅、マンガン、酸化バナジウムのアゾ金属キレート化合物は、光記録材料として光学特性が優れている。
【００３０】
上記一般式において、置換基Ｙの具体例は、例えば、ハロゲン原子、ニトロ原子、シアノ基、水酸基、カルボキシ基、アミノ基、カルバモイル基、置換もしくは未置換のアルキル基、置換もしくは未置換のアリール基、置換もしくは未置換のアルキルオキシ基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換のアルキルアミノ基、置換もしくは未置換のアリールアミノ基、置換もしくは未置換のアルキルオキシカルボニル基、置換もしくは未置換のアリールオキシカルボニル基、置換もしくは未置換のアルキルカルボニルアミノ基、置換もしくは未置換のアリールカルボニルアミノ基、置換もしくは未置換のアルキルカルバモイル基、置換もしくは未置換のアリールカルバモイル基又は置換もしくは未置換のアルケニル基を表している。
【００３１】
次に、本発明に係る記録媒体に必要な性質について説明する。記録層を構成するのに必要な性質として、光学特性と熱的特性とが挙げられる。
光学特性に必要な条件としては、記録再生波長である６３０ｎｍ〜６９０ｎｍに対して短波長側に大きな吸収帯を有し、かつ、記録再生波長が該吸収帯の長波長端近傍にあることが必要である。これは、記録再生波長である６３０ｎｍ〜６９０ｎｍで大きな屈折率と消衰係数を有することを意味するものである。
具体的には、記録再生波長近傍の長波長近傍の波長域光に対する記録層単層の屈折率ｎは、１．５以上かつ３．０以下であり、かつ、消衰係数ｋが０．０２以上かつ０．２以下の範囲にあることが好ましい。屈折率ｎが１．５未満の場合には、十分な光学的変化得られにくいため、記録変調度が低くなるため好ましくなく、また、屈折率ｎが３．０を超える場合には、波長依存性が高くなり過ぎるため、記録再生波長領域であってもエラーとなってしまうため好ましくない。また、消衰係数ｋが０．０２未満の場合には、記録感度が悪くなるため好ましくなく、消衰係数ｋが０．２を越える場合には、５０％以上の反射率を得ることが困難となるので好ましくない。
【００３２】
熱的に必要な条件としては、熱重量分析に於ける主減量過程での重量減量が、温度に対して急であることが必要である。主減量過程により有機材料膜は分解し、膜厚の減少と光学定数の変化を起こし、光学的な意味での記録部が形成されるからである。したがって、主減量過程の重量減量が温度に対して穏やかな場合、これは広い温度範囲にわたって形成されてしまうため、高密度の記録部を形成させる場合は極めて不利となる。同様な理由で重量減量の過程が複数存在する材料を用いた場合も高密度対応には不利である。
【００３３】
本発明では、いくつかの重量減量過程のうちで、減量率が最大のものを主減量過程と呼ぶ。
本発明において重量減量の傾きは下記のように求める。図７に示すように、質量Ｍ０の有機材料を窒素雰囲気下中で、１０℃／ｍｉｎ．で昇温させる。この昇温に従って、質量は微量づつ減少し、ほぼ直線ａ−ｂの重量減量線を示し、ある温度に達すると急激な重量減少を起こし、ほぼ直線ｃ−ｄに沿って重量減量を起こす。さらに温度を上げ続けると、質量の急激な減量が終了し、ほぼ直線ｅ−ｆに沿った重量減少を起こす。直線ａ−ｂと直線ｃ−ｄとの交点に於ける温度をＴ１（℃）、初期質量Ｍ０に対する残存重量をｍ１（％）、直線ｃ−ｄと直線ｅ−ｆとの交点に於ける温度をＴ２（℃）、初期質量Ｍ０に対する残存重量をｍ２（％）とすると、原料開始温度はＴ１、減量終了温度はＴ２となり、重量減量の傾きは、
（ｍ１−ｍ２）（％）／（Ｔ２−Ｔ１）（℃）
で示され、初期重量に対する重量減量率は、
（ｍ１−ｍ２）（％）
で示される。
【００３４】
上記定義に基づくと、光情報記録媒体に用いる記録材料としては、主減量過程に於ける重量減量の傾きが２％／℃以上であることが好ましい。この重量減量の傾きが２％／℃未満である記録材料を用いると、記録部の広がりが大きくなり、また、短い記録部を形成することが困難となるため、情報記録媒体には不向きである。
【００３５】
また、主減量過程に於ける重量減少率は、３０％以上であることが好ましい。３０％未満であると、良好な記録変調度、記録感度が得られない可能性がある。更に、熱的特性に必要な条件は、重量開始温度Ｔ１がある温度範囲にあることが必要である。具体的には、減量開始温度が３５０℃以下であり、好ましくは２００〜３５０℃の範囲にあることが望ましい。減量開始温度が３５０℃を超えると、記録レーザ光のパワーが高くなりすぎて実用的でなくなり、また２００℃未満であると再生劣化を起こすなど記録安定性が悪化する。
【００３６】
基板形状に必要な条件としては、基板上のトラックピッチが０．７〜０．８μｍであり、溝幅が半値幅で、０．２０〜０．３６μｍであるのが好ましい。基板は、通常、深さ１０００〜２５００Åの案内溝を有していて、トラックピッチは、通常、０．７〜１．０μｍであるが、高容量化の用途には、０．７〜０．８μｍが好ましい。溝幅は、半値幅で０．１８〜０．３６μｍが好ましい。溝幅の半値幅が０．１８μｍ未満では、十分なトラッキングエラー信号強度を得ることが困難となる恐れがある。また、溝幅の半値幅が０．３６μｍを越える場合には、記録したときに記録部が横に広がりやすくなるので好ましくない。
【００３７】
本発明に係る光記録媒体は、通常の追記型光ディスクの構造（図１、図５）、図１又は図５を２枚貼合わせた、いわゆるエアーサンドイッチ、もしくは密着貼合わせ構造（図２、図６）からなるＣＤ−Ｒ用メディアの構造としてもよい。
【００３８】
図１ないし図６に示すように、本発明に係る記録媒体は、第１基板（１）と第２基板（１）とを記録層（２）を介して接着剤で貼り合わせた構造を基本構造とする。記録層（２）は、有機色素層が単層でもよく、反射率を高めるため有機色素層と金属反射層（６）との積層でもよい。記録層（２）と基板（１）の間には、下引き層（３）あるいは保護層（４）を介在させてもよく、機能向上のためそれらを積層化した構成でもよい。特に用いられているのは、第１基板（１）／有機色素層（２）／金属反射層（６）／保護層（４）／接着層（７）／第２基板（１）からなる構造である。
【００３９】
本発明に係る記録媒体の構成要素について詳述する。
（基板）
本発明に係る記録媒体の基板の必要特性としては、基板側より記録、再生を行う場合のみ、使用レーザ光に対して透明でなければならないが、記録層側から記録、再生を行う場合には、基板は必ずしも透明である必要はない。従って、本発明に係る記録媒体においては、基板を１枚しか用いない場合は、上記した第２基板のみが透明であれば、第１基板は、透明であっても、不透明であってもよい。
使用される基板材料としては、例えば、ポリエステル、アクリル樹脂、ポリアミド、ポリカーボネート樹脂、ポリオレフィン樹脂、フェノール樹脂、エポキシ樹脂、ポリイミド等のプラスチック、ガラス、セラミックあるいは金属等を用いることができる。尚、基板を１層しか用いない場合あるいは基板２枚をサンドイッチ状で用いる場合には、上記第１基板の表面にトラッキング用の案内溝や案内ピット、さらにアドレス信号等のプレフォーマットが形成されている必要がある。
【００４０】
（中間層）
下引き層等を含め、基板、記録層、反射層、保護層以外に設けられた層をここでは中間層と呼ぶことにする。この中間層は、例えば、（ａ）接着性の向上、（ｂ）水、もしくはガス等のバリアー、（ｃ）記録層の保存安定性の向上、（ｄ）反射率の向上、（ｅ）溶剤からの基板や記録層の保護、（ｆ）案内溝・案内ピット・プレフォーマット等の形成等を目的として使用される。
（ａ）接着性の向上の目的に対しては、高分子材料、例えば、アイオノマー樹脂、ポリアミド樹脂、ビニル系樹脂、天然樹脂、天然高分子、シリコーン、液状ゴム等の種々の高分子物質、及びシランカップリング剤等を用いることができる。
（ａ）接着性の向上、（ｂ）水、もしくはガス等のバリアー及び（ｃ）記録層の保存安定性の向上の目的に対しては、上記高分子材料以外に無機化合物、例えばＳｉＯ2、ＭｇＦ2、ＳｉＯ、ＴｉＯ2、ＺｎＯ、ＴｉＮ、ＳｉＮ等金属、又は半金属、例えばＺｎ、Ｃｕ、Ｎｉ、Ｃｒ、Ｇｅ、Ｓｅ、Ａｕ、Ａｇ、Ａｌ等を用いることができる。
（ｄ）反射率の向上の目的に対しては金属、例えばＡｌ、Ａｇ等や、金属光沢を有する有機薄膜、例えばメチン染料、キサンテン系染料等を用いることができる。
（ｅ）溶剤からの基板や記録層の保護及び（ｆ）案内溝・案内ピット・プレフォーマット等の形成の目的に対しては、紫外線硬化樹脂、熱硬化樹脂、熱可塑性樹脂等を用いることができる。
中間層の膜厚は、一般には、０．０１〜３０μｍ程度、好ましくは０．０５〜１０μｍ程度が適当である。
【００４１】
（記録層）
記録層は、レーザ光の照射により何らかの光学的変化を生じさせ、その変化により情報を記録できるものであって、この記録層中には本発明の色素が含有されていることが必要である。記録層の形成にあたっては、上記色素を１種又は２種以上の組合せで用いてもよい。さらに、上記色素は、光学特性、記録感度、信号特性等の向上の目的で他の有機色素及び金属又は金属化合物と混合又は積層化してもよい。使用できる有機色素の例としては、ポリメチン色素、ナフタロシアニン系、フタロシアニン系、スクアリリウム系、クロコニウム系、ピリリウム系、ナフトキノン系、アントレキノン（インダンスレン）系、キサンテン系、トリフェニルメタン系、アズレン系、テトレヒドロコリン系、フェナンスレン系、トリフェノチアジン系染料、及び金属キレート化合物等が挙げられ、上記染料は単独で用いてもよいし、２種以上の組合せで使用してもよい。
【００４２】
また、上記染料中には、金属又は金属化合物、例えば、Ｉｎ、Ｔｅ、Ｂｉ、Ｓｅ、Ｓｂ、Ｇｅ、Ｓｎ、Ａｌ、Ｂｅ、ＴｅＯ2、ＳｎＯ、Ａｓ、Ｃｄ等を分散混合あるいは積層の形態で用いることもできる。さらに、上記染料中には、高分子材料、例えば、アイオノマー樹脂、ポリアミド系樹脂、ビニル系樹脂、天然高分子、シリコーン、液状ゴム等の種々の材料もしくはシランカップリング剤等を分散、混合して用いてもよいし、あるいは特性改良の目的で安定剤（例えば、遷移金属錯体）、分散剤、難燃剤、滑剤、帯電防止剤、界面活性剤、可塑剤等と一緒に用いることもできる。
【００４３】
記録層は、蒸着、スパッタリング、ＣＶＤ又は溶液塗布等の通常の手段によって形成することができる。塗布法を用いる場合には、上記染料等を有機溶媒等に溶解して、スプレー、ローラーコーティング、ディッピング又はスピンコーティング等の慣用のコーティング法によって行われる。
【００４４】
用いられる有機溶剤としては、一般に、メタノール、エタノール、イソプロパノール等のアルコール類、アセトン、メチルエチルケトン、シクロヘキサノン等のケトン類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド等のアミド類、ジメチルスルホキシド等のスルホキシド類、テトラヒドロフラン、ジオキサン、ジエチルエーテル、エチレングリコールモノメチルエーテル等のエーテル類、酢酸メチル、酢酸エチル等のエステル類、クロロホルム、塩化メチレン、ジクロロエタン、四塩化炭素、トリクロロエタン等の脂肪族ハロゲン化炭化水素類あるいはベンゼン、キシレン、モノクロロベンゼン、ジクロロベンゼン等の芳香族類、メトキシエタノール、エトキシエタノール等のセロソルブ類、ヘキサン、ペンタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素類等を用いることができる。
記録層の膜厚は、一般に、１００Å〜１０μｍ程度、好ましくは２００Å〜２０００Å程度が適当である。
【００４５】
（金属反射層）
反射層としては、単体で高反射率の得られかつ腐食されにくい金属又は半金属等が使用される。かかる材料の例としては、例えば、Ａｕ、Ａｇ、Ｃｒ、Ｎｉ、Ａｌ、Ｆｅ、Ｓｎ等が挙げられるが、反射率、生産性の点からは、Ａｕ、Ａｇ、Ａｌ、が特に好ましく、これらの金属又は半金属は単独で使用してもよく、２種の合金としてもよい。
膜形成法としては、例えば、蒸着、スッパタリング等の慣用の方法が挙げられ、膜厚としては、一般に、５０〜５０００Å程度、好ましくは１００〜３０００Å程度である。
【００４６】
（保護層及び基板表面ハードコート層）
保護層又は基板面ハードコート層は、（ａ）記録層（反射吸収層）を傷、ホコリ、汚れ等から保護する、（ｂ）記録層（反射吸収層）の保存安定性の向上、（ｃ）反射率の向上等を目的として使用される。これらの目的に対しては、上記中間層に示した材料を用いることができる。また、保護層及び基板表面ハードコート層には、無機材料としては、ＳｉＯ、ＳｉＯ2等が使用でき、有機材料としては、ポリメチルアクリレート、ポリカーボネート、エポキシ樹脂、ポリスチレン、ポリエステル樹脂、ビニル樹脂、セルロース、脂肪族炭化水素樹脂、芳香属炭化水素樹脂、天然ゴム、スチレンブタジエン樹脂、クロロプレンゴム、ワックス、アルキッド樹脂、乾性油、ロジン等の熱軟化性もしくは熱溶融性樹脂が使用できる。
上記材料のうち、保護層又は基板表面ハードコート層に特に好ましい例としては、生産性に優れた紫外線硬化樹脂が挙げられる。保護層又は基板面ハードコート層の膜厚は、一般に、０．０１〜３０μｍ程度、好ましくは０．０５〜１０μｍ程度が適当である。
本発明において、上記下中間層、保護層、及び基板面ハードコート層には、記録層の場合と同様に、安定剤、分散剤、難燃剤、滑剤、帯電防止剤、界面活性剤、可塑剤等を含有させることができる。
【００４７】
【発明の効果】
上記の通り、本発明によれば、７００ｎｍ以下の波長域のレーザ光で記録、再生が可能であり、かつ、耐光性、保存安定性に優れた光記録媒体が提供される。また、本発明によれば、安定した高反射率かつ高変調度で記録、再生ができる光記録媒体が提供できる。更に、本発明によれば、高密度記録ができかつ安定して記録再生できる光記録媒体が提供できる。
【００４８】
【実施例】
以下実施例により本発明をさらに詳細に説明する。
【００４９】
本発明の第１の形態における実施例として、下記の化合物を合成した。なお、本発明は、下記実施例には一切限定されるものではなく、上記一般式に包含される化合物であれば、当然のことながら、いずれも使用することができる。
【００５０】
【表１】
本発明の第２の形態における実施例として、下記の化合物を合成した。なお、本発明は、下記実施例には一切限定されるものではなく、上記一般式に包含される化合物であれば、当然のことながら、いずれも使用することができる。
【００５２】
【表４】
本発明の第３の形態における実施例として、下記の化合物を合成した。なお、本発明は、下記実施例には一切限定されるものではなく、上記一般式に包含される化合物であれば、当然のことながら、いずれも使用することができる。
【００５４】
【表７】
実施例１
厚さ０．６ｍｍの射出成形ポリカーボネート基板上に、フォトポリマーにて深さ１７５０Å、半値幅０．２５μｍ、トラックピッチ０．７４μｍの案内溝を形成し、化合物例Ｎｏ．１の１，１，２，２−テトラフルオロプロパノール溶液をスピンナー塗布し、厚さ９００Åの記録層を形成し、ついでスパッタ法により金１２００Åの反射層を設けた。さらに、その上にアクリル系フォトポリマーにて７μｍの保護層を設けた後、厚さ０．６ｍｍの射出成形ポリカーボネート平面基板をアクリル系フォトポリマーにて接着し、光記録媒体とした。
【００５６】
実施例２〜１６
実施例１で、化合物Ｎｏ．１の代わりに、化合物例Ｎｏ．２〜１６を用いた以外は、実施例１と同様にして光記録媒体を形成した。
【００５７】
実施例１７
厚さ０．６ｍｍの射出成形ポリカーボネート基板上に、フォトポリマーにて深さ１７５０Å、半値幅０．２５μｍ、トラックピッチ０．７４μｍの案内溝を形成し、化合物例Ｎｏ．１７の化合物溶液をスピンナー塗布し、厚さ９００Åの記録層を形成し、ついでスパッタ法により金１２００Åの反射層を設けた。さらに、その上にアクリル系フォトポリマーにて７μｍの保護層を設けた後、厚さ０．６ｍｍの射出成形ポリカーボネート平面基板をアクリル系フォトポリマーにて接着し、光記録媒体とした。
【００５８】
実施例１８〜３２
実施例１７で、化合物Ｎｏ．１７の代わりに、化合物例Ｎｏ．１８〜３２を用いた以外は、実施例１７と同様にして光記録媒体を形成した。
【００５９】
実施例３３
厚さ０．６ｍｍの射出成形ポリカーボネート基板上に、フォトポリマーにて深さ１７５０Å、半値幅０．２５μｍ、トラックピッチ０．７４μｍの案内溝を形成し、化合物例Ｎｏ．３３の化合物溶液をスピンナー塗布し、厚さ９００Åの記録層を形成し、ついでスパッタ法により金１２００Åの反射層を設けた。さらに、その上にアクリル系フォトポリマーにて７μｍの保護層を設けた後、厚さ０．６ｍｍの射出成形ポリカーボネート平面基板をアクリル系フォトポリマーにて接着し、記録媒体とした。
【００６０】
実施例３４〜４８
実施例３３で、化合物Ｎｏ．３３の代わりに、化合物例Ｎｏ．３４〜４８を用いた以外は、実施例３３と同様にして光記録媒体を形成した。
【００６１】
比較例１
実施例１で、化合物例Ｎｏ．１の代わりに、以下に示す化合物（比−１）を用いた以外は、実施例１と同様にして記録媒体を形成した。
【化２２】
（記録条件）
上記実施例で得た光記録媒体に、レーザ発振波長６５８ｎｍ、ビーム径１．０μｍの半導体レーザ光を用い、トラッキングしながら、ＥＦＭ信号（線速３．５ｍ／ｓｅｃ．）を記録し、発振波長６８５ｎｍの半導体レーザの連続光（再生パワー０．７ｍＷ）で再生し、再生波形を観察した。
【００６３】
（耐候テスト条件）
耐光テスト ：４万Ｌｕｘ、Ｘｅ光、２０時間連続照射
保存テスト ：６０℃ ９０％ ６００時間放置
【００６４】
【表１０】
【表１１】
【表１２】
【図面の簡単な説明】
【図１】本発明の第１の形態における通常の追記型光記録媒体の模式図。
【図２】本発明の第１の形態におけるＣＤ−Ｒ用の媒体構成を示す模式図。
【図３】本発明の第１の形態におけるＤＶＤ−Ｒ用の媒体構成を示す模式図。
【図４】本発明の第２の形態における通常の追記型光記録媒体の模式図。
【図５】本発明の第２の形態におけるＣＤ−Ｒ用の媒体構成を示す模式図。
【図６】本発明の第２の形態におけるＤＶＤ−Ｒ用の媒体構成を示す模式図。
【図７】有機材料の主減量過程、重量減量率を求める方法を説明する図。
【符号の説明】
１： 基板
２： 記録層
３： 下引き層
４： 保護層
５： ハ−ドコート層
６： 金属反射層
７： 保護基板
８： 接着層[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a large capacity write once optical recording medium for data (large capacity write once compact disc, DVD-R). The large capacity write once optical recording medium for data according to the present invention can also be applied to a large capacity optical card.
[0002]
[Prior art]
Currently, DVD-R is being developed as a next generation large capacity optical disk. Elemental technologies for improving the recording capacity include the development of recording materials for minimizing recording pits, the use of image compression techniques represented by MPEG2, and the shortening of the wavelength of a semiconductor laser for recording pit reading. Development is necessary.
[0003]
Up until now, only 670 nm band AlGaInP laser diodes have been commercialized for bar code readers and measuring instruments as semiconductor lasers in the red wavelength range. It is being used in the optical storage market. In the case of a DVD drive, the light source is standardized with two wavelengths of a laser diode of 635 nm band and 650 nm band. For high-density recording, it is desirable that the wavelength is shorter, and the wavelength of 635 nm is preferable as a drive for additional recording media. On the other hand, a read-only DVD-ROM drive is commercialized with a wavelength of ˜650 nm.
[0004]
A DVD-R medium that is particularly preferable under such circumstances is a medium that can be recorded and reproduced at a wavelength of 635 nm and can be reproduced at a wavelength of 650 nm. However, a recording material that has excellent light resistance and storage stability and can be recorded and reproduced with an optical pickup using a laser of 650 nm or less has not been developed yet.
[0005]
As a conventional technique of a write-once optical recording medium (WORM) (for information recording), a cyanine dye is used as a recording material (for example, JP-A-57-82093), and a phthalocyanine dye is used as a recording material ( For example, JP-A 61-150243 and the like. Further, as a prior art of a recordable compact disc (CD-R), a cyanine dye + metal reflective layer is used as a recording material (for example, JP-A-1-159842), and a phthalocyanine dye + metal reflective layer is used as a recording material. (For example, Japanese Patent Laid-Open No. 1-176585), and those using an azo metal chelate dye + metal reflective layer as a recording material (for example, Japanese Patent Laid-Open No. 4-46186).
[0006]
Further, as a prior art of a large capacity write-once compact disc (DVD-R), for example, an imidazole azomethine dye + metal reflective layer is used as a recording material (for example, JP-A-8-198872, 8-209902, 8-283263).
[0007]
As a result of diligent study of various dye compounds, the present inventors applied to a next-generation large-capacity optical disk system using a semiconductor laser having an oscillation wavelength of 700 nm or less by using a recording layer mainly composed of a dye having a specific structure. Found that is possible.
[0008]
In addition, the present inventors can improve the solubility, control the thermal characteristics, improve the stability of the metal complex by limiting a part of the structure of the recording material, easy to handle, high density It has been found that an optical recording medium that is recordable and has high light resistance can be provided.
[0009]
[Problems to be solved by the invention]
Therefore, the present invention is a light having a recording layer made of a recording material excellent in light resistance and storage stability, which can be applied to a DVD-R disk system using a semiconductor laser having an oscillation wavelength at a shorter wavelength than in the conventional system. It is an object to provide a recording medium.
[0010]
[Means for Solving the Problems]
According to the present invention, in order to solve the above problems, the following optical recording medium is provided.
(1) In an optical recording medium having a recording layer provided on a substrate, the following general formula (I):
[Chemical 8]
R 1 ~ R Three Each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryl group, an amino group, a substituted or unsubstituted alkylamino group or a substituted group. Alternatively, it represents an unsubstituted dialkylamino group. Or general formula (II):
[Chemical 9]
R 1 ~ R Three Each have the same meaning as described above. Or general formula (III):
[Chemical Formula 10]
R Four And R Five Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and when it is a substituted or unsubstituted alkyl group, it is bonded to form a crown. Also good. )
And an azo metal chelate compound comprising a metal, a metal oxide or a salt thereof in the recording layer.
(2) In the optical recording medium described in (1), the azo compound is represented by the following general formula (IV):
Embedded image
R 1 ~ R Three Has the same meaning as above. )
An optical recording medium characterized by being a heterocyclic compound represented by the formula:
(3) In the optical recording medium according to (1) or (2), the azo compound has the following general formula (V):
Embedded image
P represents a condensed ring structure which may contain a hetero atom,
Yn represents an integer of n substituents directly bonded to the heterocyclic ring (when n = 0, it indicates that no substituent is present).
An optical recording medium characterized by being a heterocyclic compound represented by the formula:
(4) In the optical recording medium described in (1) above, the azo compound is represented by the following general formula (VI):
Embedded image
(5) In the optical recording medium described in (1) above, the azo compound is represented by the following general formula (VII):
Embedded image
An optical recording medium characterized by being a heterocyclic compound represented by the formula:
(6) The optical recording medium according to any one of (1) to (5) above, wherein the metal or metal oxide of the azo metal chelate compound is divalent or trivalent. Medium.
(7) The optical recording medium according to any one of (1) to (6) above, wherein the metal atom of the azo metal chelate compound is cobalt, nickel, copper, or manganese. .
(8) In the optical recording medium according to any one of (1) to (7), the refractive index n of the recording layer single layer with respect to light in the wavelength range of recording / reproducing wavelength ± 5 nm is 1.5 ≦ n ≦. An optical recording medium having 3.0 and an extinction coefficient k of 0.02 ≦ k ≦ 0.20.
(9) The optical recording medium according to any one of (1) to (8), wherein the optical recording medium has the following properties (a), (b), or (c).
(A) The recording layer is optically changed by a laser beam having a wavelength of 600 nm to 700 nm.
(B) In thermogravimetric analysis of organic dyes, the slope of weight loss with respect to temperature in the main weight loss process is 2% / ° C or more.
(C) The total weight loss in the main weight loss process is 25% or more in thermogravimetric analysis of organic dyes.
(10) In the optical recording medium according to any one of (1) to (9), the track pitch on the substrate is 0.7 to 0.8 μm, and the groove width is 0.20 to half width. An optical recording medium having a thickness of 0.36 μm.
[0011]
DETAILED DESCRIPTION OF THE INVENTION
The present invention will be described in detail below.
The novel azo compounds that can be used in the first aspect of the present invention are represented by the general formula (I):
Embedded image
R 1 ~ R Three Each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryl group, an amino group, a substituted or unsubstituted alkylamino group or a substituted group. Alternatively, it represents an unsubstituted dialkylamino group. )
It is a heterocyclic compound represented by these.
[0012]
Among the azo compounds represented by the above general formula (I), preferred compounds are those represented by the general formula (IV):
Embedded image
R 1 ~ R Three Has the same meaning as above. )
The heterocyclic compound represented by these is mentioned.
[0013]
Among the azo compounds represented by the above general formula (I), preferred compounds are those represented by the general formula (V):
Embedded image
P represents a condensed ring structure that may contain a hetero atom;
Y represents an integer of n substituents directly bonded to the heterocyclic ring (when n = 0, it represents that no substituent is present))
The heterocyclic compound represented by these is mentioned.
[0014]
The novel azo compounds that can be used in the second aspect of the present invention have the general formula (II):
Embedded image
R 1 ~ R Three Each have the same meaning as described above. )
It is a heterocyclic compound represented by these.
[0015]
In a preferred embodiment of the second aspect of the present invention, the azo compound is represented by the following general formula (VI):
Embedded image
The heterocyclic compound represented by these is mentioned.
[0016]
The novel azo compounds that can be used in the third aspect of the present invention have the general formula (III):
Embedded image
R Four And R Five Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. )
The heterocyclic compound represented by these is mentioned.
[0017]
In a preferred embodiment of the third aspect of the present invention, the azo compound is represented by the following general formula (VII):
Embedded image
The heterocyclic compound represented by these is mentioned.
[0018]
In the above general formula, examples of the halogen atom include fluorine, chlorine, bromine, and iodine.
In the above general formula, the alkyl group means a monovalent straight chain, branched chain or cyclic aliphatic hydrocarbon residue, and examples of the alkyl group include, for example, a methyl group, an ethyl group, n Primary alkyl group such as -propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, isobutyl group, isoamyl group, 2-methylbutyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 2-ethylbutyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl Group, 2-ethylpentyl group, 3-ethylpentyl group, 2-methylheptyl group, 3-methylheptyl group, 4-methylheptyl group, 5-methylheptyl group, 2-ethylheptyl group Sil group, 3-ethylhexyl group, isopropyl group, sec-butyl group, 1-ethylpropyl group, 1-methylbutyl group, 1,2-dimethylpropyl group, 1-methylheptyl group, 1-ethylbutyl group, 1,3- Dimethylbutyl group, 1,2-dimethylbutyl group, 1-ethyl-2-methylpropyl group, 1-methylhexyl group, 1-ethylheptyl group, 1-propylbutyl group, 1-isopropyl-2-methylpropyl group, 1-ethyl-2-methylbutyl group, 1-ethyl-2-methylbutyl group, 1-propyl-2-methylpropyl group, 1-methylheptyl group, 1-ethylhexyl group, 1-propylpentyl group, 1-isopropylpentyl group 1-isopropyl-2-methylbutyl group, 1-isopropyl-3-methylbutyl group, 1-methyloctyl group, 1 Secondary alkyl groups such as ethylheptyl group, 1-propylhexyl group, 1-isobutyl-3-methylbutyl group, neopentyl group, tert-butyl group, tert-hexyl group, tert-amyl group, tert-octyl group, etc. Cycloalkyl such as primary alkyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-ethylcyclohexyl group, 4-tert-butylcyclohexyl group, 4- (2-ethylhexyl) cyclohexyl group, bornyl group, isobornyl group (adamantane group) Groups and the like. Furthermore, these primary and secondary alkyl groups are substituted with, for example, a hydroxyl group, a halogen atom, a nitro group, a carboxy group, a cyano group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic residue, and the like. It may also be substituted with the above alkyl group through an atom such as oxygen, sulfur, or nitrogen.
[0019]
Furthermore, examples of the alkyl group substituted through oxygen include a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an ethoxyethyl group, a butoxyethyl group, an ethoxyethoxyethyl group, a phenoxyethyl group, a methoxypropyl group, Examples thereof include an ethoxypropyl group, a piperidino group, a morpholino group, and the alkyl group substituted via sulfur includes, for example, a methylthioethyl group, an ethylthioethyl group, an ethylthiopropyl group, a phenylthioethyl group, and the like. Examples of the alkyl group substituted via nitrogen include dimethylaminoethyl group, diethylaminoethyl group, diethylaminopropyl group and the like.
[0020]
In the above general formula, the alkoxy group may be any group in which a substituted or unsubstituted alkyl group is directly bonded to an oxygen atom, and specific examples of the alkyl group include the specific examples described above.
[0021]
In the above general formula, the aryloxy group may be any group in which a substituted or unsubstituted aryl group is directly bonded to an oxygen atom. Specific examples of such aryl groups include, for example, a phenyl group, a pentalenyl group, an indenyl group. Group, naphthyl group, azulenyl group, heptalenyl group, biphenylenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group and the like.
[0022]
In the above general formula, the alkoxycarbonyl group may be any group in which a substituted or unsubstituted alkyl group is directly bonded to the oxygen atom of the alkoxycarbonyl group. Specific examples of the alkyl group include the specific examples described above. be able to.
[0023]
In the above general formula, the aryloxycarbonyl group may be any group in which a substituted or unsubstituted aryl group is directly bonded to the oxygen atom of the aryloxycarbonyl group. Specific examples of such aryl groups include those described above. An example can be given.
[0024]
In the above general formula, the carbamoyl group may be any group in which a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group is directly bonded to the nitrogen atom of the carbamoyl group. Specific examples of the alkyl group and aryl group include the above-described specific examples.
[0025]
In the above general formula, the acyl group may be any one in which a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group is directly bonded to the carbonyl carbon atom of the acyl group. The above-mentioned specific examples can be given as examples.
[0026]
In the above general formula, the amino group may be any group in which a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group is directly bonded to a nitrogen atom. Specific examples of such an alkyl group and aryl group include Specific examples can be given.
[0027]
In the above general formula, specific examples of the heterocyclic residue include indolyl group, furyl group, thienyl group, pyridyl group, piperidyl group, quinolyl group, isoquinolyl group, piperidino group, morpholino group, pyrrolyl group and the like. .
[0028]
In the above general formula, R 1 And R 2 Specific examples of the amino group formed by linking with each other include piperidino group, morpholino group, pyrrolidyl group, piperazyl group, imidazolidyl group, pyrazolidyl group, indolinyl group, isoindolinyl group, pyrrolyl group, indolyl group, isoindolyl group, carbazolyl group Etc.
[0029]
In the above general formula, specific examples of the divalent or trivalent metal atom include, for example, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zirconium, niobium, molybdenum, technenium, ruthenium, rhodium, palladium, and the like. Specific examples of metal oxides include vanadium oxide and the like. In particular, azo metal chelate compounds of cobalt, nickel, copper, manganese, and vanadium oxide have excellent optical characteristics as optical recording materials.
[0030]
In the above general formula, specific examples of the substituent Y include, for example, a halogen atom, nitro atom, cyano group, hydroxyl group, carboxy group, amino group, carbamoyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group Substituted or unsubstituted alkyloxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylamino group, substituted or unsubstituted aryl Amino group, substituted or unsubstituted alkyloxycarbonyl group, substituted or unsubstituted aryloxycarbonyl group, substituted or unsubstituted alkylcarbonylamino group, substituted or unsubstituted arylcarbonylamino group, substituted or unsubstituted alkylcarbamoyl Group, substitution or It represents the unsubstituted arylcarbamoyl group, or a substituted or unsubstituted alkenyl group.
[0031]
Next, properties necessary for the recording medium according to the present invention will be described. Properties necessary for constituting the recording layer include optical properties and thermal properties.
Necessary conditions for optical characteristics include a large absorption band on the short wavelength side with respect to the recording / reproducing wavelength of 630 nm to 690 nm, and the recording / reproducing wavelength must be near the long wavelength end of the absorption band. It is. This means that it has a large refractive index and extinction coefficient at a recording / reproducing wavelength of 630 nm to 690 nm.
Specifically, the refractive index n of the recording layer single layer with respect to light in the wavelength range near the long wavelength near the recording / reproducing wavelength is 1.5 or more and 3.0 or less, and the extinction coefficient k is 0.02. It is preferable that it exists in the range above and below 0.2. When the refractive index n is less than 1.5, it is difficult to obtain a sufficient optical change, which is not preferable because the recording modulation degree becomes low. When the refractive index n exceeds 3.0, the wavelength dependence Therefore, it is not preferable because an error occurs even in the recording / reproducing wavelength region. Further, when the extinction coefficient k is less than 0.02, it is not preferable because the recording sensitivity is deteriorated. When the extinction coefficient k exceeds 0.2, it is difficult to obtain a reflectance of 50% or more. Therefore, it is not preferable.
[0032]
As a necessary condition for heat, weight loss in the main weight loss process in thermogravimetric analysis needs to be abrupt with respect to temperature. This is because the organic material film is decomposed by the main weight reduction process, causing a decrease in film thickness and a change in optical constant, thereby forming a recording portion in an optical sense. Accordingly, when the weight loss in the main weight loss process is moderate with respect to the temperature, this is formed over a wide temperature range, which is extremely disadvantageous when forming a high-density recording portion. For the same reason, the use of a material having a plurality of weight loss processes is also disadvantageous for high density.
[0033]
In the present invention, among several weight loss processes, the one with the largest weight loss rate is called the main weight loss process.
In the present invention, the weight loss slope is determined as follows. As shown in FIG. 7, an organic material having a mass of M0 was placed at 10 ° C./min. Raise the temperature at. As the temperature rises, the mass decreases by a small amount and shows a weight loss line of a substantially straight line ab. When a certain temperature is reached, a sudden weight loss occurs, and a weight loss occurs almost along a straight line cd. When the temperature is further increased, the mass suddenly loses weight, and the weight is reduced substantially along the straight line ef. The temperature at the intersection of the straight line ab and the straight line cd is T1 (° C.), the remaining weight with respect to the initial mass M0 is m1 (%), and the temperature at the intersection of the straight line cd and the straight line ef Is T2 (° C.) and the remaining weight with respect to the initial mass M0 is m2 (%), the raw material start temperature is T1, the weight loss end temperature is T2, and the weight loss slope is
(M1-m2) (%) / (T2-T1) (° C.)
The weight loss rate with respect to the initial weight is
(M1-m2) (%)
Indicated by
[0034]
Based on the above definition, the recording material used for the optical information recording medium preferably has a weight loss gradient of 2% / ° C. or more in the main weight loss process. When a recording material having a weight loss gradient of less than 2% / ° C. is used, the recording area becomes large and it becomes difficult to form a short recording area, which is not suitable for an information recording medium. .
[0035]
The weight reduction rate in the main weight loss process is preferably 30% or more. If it is less than 30%, good recording modulation degree and recording sensitivity may not be obtained. Furthermore, the necessary condition for the thermal characteristics is that the weight start temperature T1 is in a certain temperature range. Specifically, the weight loss starting temperature is 350 ° C. or lower, preferably in the range of 200 to 350 ° C. When the weight loss starting temperature exceeds 350 ° C., the power of the recording laser beam becomes too high to be practical, and when it is less than 200 ° C., the recording stability deteriorates such as causing deterioration in reproduction.
[0036]
As conditions necessary for the substrate shape, it is preferable that the track pitch on the substrate is 0.7 to 0.8 [mu] m, and the groove width is a half value width of 0.20 to 0.36 [mu] m. The substrate usually has a guide groove with a depth of 1000 to 2500 mm, and the track pitch is usually 0.7 to 1.0 μm. 8 μm is preferable. The groove width is preferably 0.18 to 0.36 [mu] m in half width. If the half width of the groove width is less than 0.18 μm, it may be difficult to obtain a sufficient tracking error signal intensity. In addition, when the half width of the groove width exceeds 0.36 μm, it is not preferable because the recording portion tends to spread laterally when recording.
[0037]
The optical recording medium according to the present invention has a structure of a normal write-once optical disc (FIGS. 1 and 5), a so-called air sandwich in which two sheets of FIG. 1 or FIG. The structure of the CD-R medium comprising 6) may be adopted.
[0038]
As shown in FIGS. 1 to 6, the recording medium according to the present invention basically has a structure in which a first substrate (1) and a second substrate (1) are bonded together with an adhesive via a recording layer (2). Structure. The recording layer (2) may be a single organic dye layer or a laminate of an organic dye layer and a metal reflective layer (6) in order to increase the reflectance. An undercoat layer (3) or a protective layer (4) may be interposed between the recording layer (2) and the substrate (1), or a structure in which they are laminated for improving the function may be used. Particularly used is a structure comprising the first substrate (1) / organic dye layer (2) / metal reflective layer (6) / protective layer (4) / adhesive layer (7) / second substrate (1). It is.
[0039]
The components of the recording medium according to the present invention will be described in detail.
(substrate)
The necessary characteristics of the substrate of the recording medium according to the present invention must be transparent to the laser beam used only when recording and reproducing from the substrate side, but when recording and reproducing from the recording layer side. The substrate does not necessarily have to be transparent. Therefore, in the recording medium according to the present invention, when only one substrate is used, if only the second substrate described above is transparent, the first substrate may be transparent or opaque. .
As a substrate material to be used, for example, polyester, acrylic resin, polyamide, polycarbonate resin, polyolefin resin, phenol resin, epoxy resin, polyimide or other plastic, glass, ceramic, metal, or the like can be used. When only one layer is used or when two substrates are used in a sandwich shape, a guide groove for tracking, a guide pit, and a preformat such as an address signal are formed on the surface of the first substrate. Need to be.
[0040]
(Middle layer)
A layer provided other than the substrate, the recording layer, the reflective layer, and the protective layer, including the undercoat layer, is referred to herein as an intermediate layer. This intermediate layer may be, for example, (a) improved adhesion, (b) a barrier such as water or gas, (c) improved storage stability of the recording layer, (d) improved reflectance, (e) solvent It is used for the purpose of protecting the substrate and the recording layer, and (f) forming guide grooves, guide pits, preformats, and the like.
(A) For the purpose of improving adhesiveness, various high molecular materials such as ionomer resins, polyamide resins, vinyl resins, natural resins, natural polymers, silicones, liquid rubbers, and the like, and A silane coupling agent or the like can be used.
For the purpose of (a) improving adhesiveness, (b) barriers such as water or gas, and (c) improving the storage stability of the recording layer, in addition to the above polymer materials, inorganic compounds such as SiO 2 , MgF 2 , SiO, TiO 2 , ZnO, TiN, SiN, or a metal, or a semimetal such as Zn, Cu, Ni, Cr, Ge, Se, Au, Ag, Al, or the like can be used.
(D) For the purpose of improving reflectivity, metals such as Al and Ag, and organic thin films having metallic luster such as methine dyes and xanthene dyes can be used.
For the purpose of (e) protecting the substrate and recording layer from the solvent and (f) forming the guide groove / guide pit / preformat, etc., it is possible to use an ultraviolet curable resin, a thermosetting resin, a thermoplastic resin, or the like. it can.
The thickness of the intermediate layer is generally about 0.01 to 30 μm, preferably about 0.05 to 10 μm.
[0041]
(Recording layer)
The recording layer is capable of causing some optical change by irradiation with laser light and recording information by the change, and the recording layer needs to contain the dye of the present invention. In forming the recording layer, the above dyes may be used alone or in combination of two or more. Furthermore, the dye may be mixed or laminated with other organic dyes and metals or metal compounds for the purpose of improving optical characteristics, recording sensitivity, signal characteristics, and the like. Examples of organic dyes that can be used include polymethine dyes, naphthalocyanine, phthalocyanine, squarylium, croconium, pyrylium, naphthoquinone, anthrequinone (indanthrene), xanthene, triphenylmethane, and azulene Tetrehydrocholine-based, phenanthrene-based, triphenothiazine-based dyes, metal chelate compounds, and the like. The above dyes may be used alone or in combination of two or more.
[0042]
Further, in the above dyes, metals or metal compounds such as In, Te, Bi, Se, Sb, Ge, Sn, Al, Be, TeO 2 SnO, As, Cd, etc. can also be used in the form of dispersion mixing or lamination. Further, in the above dye, various materials such as ionomer resin, polyamide resin, vinyl resin, natural polymer, silicone, liquid rubber, or silane coupling agent are dispersed and mixed in the dye. Alternatively, they may be used together with stabilizers (for example, transition metal complexes), dispersants, flame retardants, lubricants, antistatic agents, surfactants, plasticizers and the like for the purpose of improving characteristics.
[0043]
The recording layer can be formed by ordinary means such as vapor deposition, sputtering, CVD or solution coating. When the coating method is used, the above-described dye or the like is dissolved in an organic solvent or the like, and is performed by a conventional coating method such as spraying, roller coating, dipping, or spin coating.
[0044]
As the organic solvent used, in general, alcohols such as methanol, ethanol and isopropanol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide and the like Sulfoxides, ethers such as tetrahydrofuran, dioxane, diethyl ether and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethane, carbon tetrachloride and trichloroethane Or aromatics such as benzene, xylene, monochlorobenzene and dichlorobenzene, cellosolves such as methoxyethanol and ethoxyethanol, hexane, pentane and Hexane, it can be used hydrocarbons such as methylcyclohexane.
The film thickness of the recording layer is generally about 100 to 10 μm, preferably about 200 to 2000 μm.
[0045]
(Metal reflective layer)
As the reflective layer, a metal or a semimetal that has a high reflectivity and is not easily corroded is used. Examples of such materials include Au, Ag, Cr, Ni, Al, Fe, Sn, etc., but Au, Ag, Al are particularly preferable from the viewpoint of reflectance and productivity. The metal or metalloid may be used alone or as two kinds of alloys.
Examples of the film forming method include conventional methods such as vapor deposition and sputtering, and the film thickness is generally about 50 to 5000 mm, preferably about 100 to 3000 mm.
[0046]
(Protective layer and hard coat layer on substrate surface)
The protective layer or substrate surface hard coat layer (a) protects the recording layer (reflection / absorption layer) from scratches, dust, dirt, etc. (b) improves the storage stability of the recording layer (reflection / absorption layer), (c ) Used for the purpose of improving the reflectance. For these purposes, the materials shown in the intermediate layer can be used. In addition, the protective layer and the substrate surface hard coat layer include inorganic materials such as SiO and SiO. 2 Organic materials such as polymethyl acrylate, polycarbonate, epoxy resin, polystyrene, polyester resin, vinyl resin, cellulose, aliphatic hydrocarbon resin, aromatic hydrocarbon resin, natural rubber, styrene butadiene resin, chloroprene rubber Further, heat softening or heat melting resins such as wax, alkyd resin, drying oil, rosin can be used.
Among the materials described above, particularly preferable examples of the protective layer or the substrate surface hard coat layer include an ultraviolet curable resin excellent in productivity. The film thickness of the protective layer or the substrate surface hard coat layer is generally about 0.01 to 30 μm, preferably about 0.05 to 10 μm.
In the present invention, the lower intermediate layer, the protective layer, and the substrate-side hard coat layer have the same stabilizers, dispersants, flame retardants, lubricants, antistatic agents, surfactants, plasticizers as in the recording layer. Etc. can be contained.
[0047]
【The invention's effect】
As described above, according to the present invention, there is provided an optical recording medium that can be recorded and reproduced with a laser beam having a wavelength of 700 nm or less, and that is excellent in light resistance and storage stability. Further, according to the present invention, an optical recording medium capable of recording and reproducing with a stable high reflectivity and a high degree of modulation can be provided. Furthermore, according to the present invention, it is possible to provide an optical recording medium capable of high-density recording and stably recording / reproducing.
[0048]
【Example】
Hereinafter, the present invention will be described in more detail with reference to examples.
[0049]
As examples in the first aspect of the present invention, the following compounds were synthesized. In addition, this invention is not limited at all to the following Example, As long as it is a compound included by the said general formula, all can be used as a matter of course.
[0050]
[Table 1]
The following compounds were synthesized as examples in the second aspect of the present invention. In addition, this invention is not limited at all to the following Example, As long as it is a compound included by the said general formula, all can be used as a matter of course.
[0052]
[Table 4]
As examples in the third aspect of the present invention, the following compounds were synthesized. In addition, this invention is not limited at all to the following Example, As long as it is a compound included by the said general formula, all can be used as a matter of course.
[0054]
[Table 7]
Example 1
On an injection molded polycarbonate substrate having a thickness of 0.6 mm, a guide groove having a depth of 1750 mm, a half width of 0.25 μm, and a track pitch of 0.74 μm was formed using a photopolymer. A 1,1,2,2-tetrafluoropropanol solution of 1 was applied by a spinner to form a recording layer having a thickness of 900 mm, and then a reflective layer having a thickness of 1200 mm was formed by sputtering. Further, a protective layer having a thickness of 7 μm was formed thereon with an acrylic photopolymer, and then an injection molded polycarbonate flat substrate having a thickness of 0.6 mm was adhered with the acrylic photopolymer to obtain an optical recording medium.
[0056]
Examples 2-16
In Example 1, compound no. In place of Compound No. 1 An optical recording medium was formed in the same manner as in Example 1 except that 2 to 16 were used.
[0057]
Example 17
On an injection molded polycarbonate substrate having a thickness of 0.6 mm, a guide groove having a depth of 1750 mm, a half width of 0.25 μm, and a track pitch of 0.74 μm was formed using a photopolymer. The compound solution of 17 was applied by a spinner to form a recording layer having a thickness of 900 mm, and a reflective layer having a thickness of 1200 mm was then formed by sputtering. Further, a protective layer having a thickness of 7 μm was formed thereon with an acrylic photopolymer, and then an injection molded polycarbonate flat substrate having a thickness of 0.6 mm was adhered with the acrylic photopolymer to obtain an optical recording medium.
[0058]
Examples 18-32
In Example 17, compound no. Instead of Compound Example No. 17 An optical recording medium was formed in the same manner as in Example 17 except that 18 to 32 were used.
[0059]
Example 33
On an injection molded polycarbonate substrate having a thickness of 0.6 mm, a guide groove having a depth of 1750 mm, a half width of 0.25 μm, and a track pitch of 0.74 μm was formed using a photopolymer. A compound solution of 33 was spinner coated to form a recording layer having a thickness of 900 mm, and a reflective layer having a thickness of 1200 mm was then formed by sputtering. Further, a protective layer having a thickness of 7 μm was formed thereon with an acrylic photopolymer, and then an injection molded polycarbonate flat substrate having a thickness of 0.6 mm was adhered with the acrylic photopolymer to obtain a recording medium.
[0060]
Examples 34-48
In Example 33, compound no. Instead of Compound No. 33, Compound Example No. An optical recording medium was formed in the same manner as in Example 33 except that 34 to 48 were used.
[0061]
Comparative Example 1
In Example 1, Compound Example No. A recording medium was formed in the same manner as in Example 1 except that the following compound (ratio-1) was used instead of 1.
Embedded image
(Recording conditions)
A semiconductor laser beam having a laser oscillation wavelength of 658 nm and a beam diameter of 1.0 μm was recorded on the optical recording medium obtained in the above example while tracking, and an EFM signal (linear velocity of 3.5 m / sec.) Was recorded. Reproduction was performed with continuous light from a 685 nm semiconductor laser (reproduction power: 0.7 mW), and the reproduction waveform was observed.
[0063]
(Weatherproof test conditions)
Light resistance test: 40,000 Lux, Xe light, 20 hours continuous irradiation
Storage test: 60 ° C 90% left for 600 hours
[0064]
[Table 10]
[Table 11]
[Table 12]
[Brief description of the drawings]
FIG. 1 is a schematic diagram of a normal write-once type optical recording medium according to a first embodiment of the present invention.
FIG. 2 is a schematic diagram showing a medium configuration for CD-R in the first embodiment of the present invention.
FIG. 3 is a schematic diagram showing a medium configuration for DVD-R in the first embodiment of the present invention.
FIG. 4 is a schematic diagram of a normal write-once type optical recording medium according to a second embodiment of the present invention.
FIG. 5 is a schematic diagram showing a medium configuration for CD-R in a second embodiment of the present invention.
FIG. 6 is a schematic diagram showing a medium configuration for DVD-R in the second embodiment of the present invention.
FIG. 7 is a diagram for explaining a method for obtaining a main weight loss process and a weight loss rate of an organic material.
[Explanation of symbols]
1: Substrate
2: Recording layer
3: Undercoat layer
4: Protective layer
5: Hard coat layer
6: Metal reflective layer
7: Protection board
8: Adhesive layer
Claims (10)
Ｒ1〜Ｒ3は、それぞれ独立して、水素原子、ハロゲン原子、置換もしくは未置換のアルキル基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアリール基、アミノ基、置換もしくは未置換のアルキルアミノ基又は置換もしくは未置換のジアルキルアミノ基を表す。）、又は一般式（II）：
Ｒ1〜Ｒ3は、それぞれ前記と同じ意味を有する。）、又は一般式（III）：
Ｒ4及びＲ5は、それぞれ独立して、水素原子、置換もしくは未置換のアルキル基又は置換もしくは未置換のアリール基を意味し、置換もしくは未置換のアルキル基である場合には、結合して冠状になっていてもよい。）
で示されるアゾ化合物と、金属、金属酸化物又はその塩からなるアゾ金属キレート化合物を少なくとも一種類を記録層中に含有することを特徴とする光記録媒体。In an optical recording medium in which a recording layer is provided on a substrate, the following general formula (I):
R 1 to R 3 are each independently a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxyl group, substituted or unsubstituted aryl group, amino group, substituted or unsubstituted An alkylamino group or a substituted or unsubstituted dialkylamino group is represented. Or general formula (II):
R 1 to R 3 each have the same meaning as described above. Or general formula (III):
R 4 and R 5 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and in the case of a substituted or unsubstituted alkyl group, It may be crowned. )
And an azo metal chelate compound comprising a metal, a metal oxide or a salt thereof in the recording layer.
Ｒ1〜Ｒ3は前記と同じ意味を有する。）
で表される複素環化合物であることを特徴とする光記録媒体。The optical recording medium according to claim 1, wherein the azo compound is represented by the following general formula (IV):
R 1 to R 3 have the same meaning as described above. )
An optical recording medium characterized by being a heterocyclic compound represented by the formula:
Ｐは、ヘテロ原子を含んでいてもよい縮合環構造を表し、
Ｙｎは、複素環に直接結合している整数ｎ個の置換基を表す（ｎ＝０の場合は置換基を有していないことを表す）
で表される複素環化合物であることを特徴とする光記録媒体。The optical recording medium according to claim 1, wherein the azo compound is represented by the following general formula (V):
P represents a condensed ring structure which may contain a hetero atom,
Yn represents an integer of n substituents directly bonded to the heterocyclic ring (when n = 0, it indicates that no substituent is present).
An optical recording medium characterized by being a heterocyclic compound represented by the formula:
で表される複素環化合物であることを特徴とする光記録媒体。The optical recording medium according to claim 1, wherein the azo compound is represented by the following general formula (VII):
An optical recording medium characterized by being a heterocyclic compound represented by the formula:
（イ）記録層が波長６００ｎｍ〜７００ｎｍのレーザ光により光学的な変化を生じるものであること。
（ロ）有機色素の熱重量分析で、主減量過程での温度に対する減量の傾きが２％／℃以上であること。
（ハ）有機色素の熱重量分析で、主減量過程での総減量が２５％以上であること。9. The optical recording medium according to claim 1, wherein the optical recording medium has the following properties (a), (b) or (c).
(A) The recording layer is optically changed by a laser beam having a wavelength of 600 nm to 700 nm.
(B) In thermogravimetric analysis of organic dyes, the slope of weight loss with respect to temperature in the main weight loss process is 2% / ° C or more.
(C) The total weight loss in the main weight loss process is 25% or more in thermogravimetric analysis of organic dyes.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI295681B (en) * | 2001-12-19 | 2008-04-11 | Ritek Corp | |
| TW594717B (en) * | 2002-06-12 | 2004-06-21 | Ritek Corp | Optical recording medium and method for making the same and dye for improving tracking signal of an optical recording medium |
| GB2396154B (en) * | 2002-10-15 | 2007-02-28 | Merck Patent Gmbh | 4,5-Dicyanoimidazole derivatives and their use in liquid crystal media and liquid crystal devices |
| JP4136834B2 (en) * | 2003-07-16 | 2008-08-20 | 富士フイルム株式会社 | Optical information recording medium |
| TW200817477A (en) | 2006-09-28 | 2008-04-16 | Fujifilm Corp | Optical information recording medium and azo-metal complx dye |
| US8092890B2 (en) | 2007-04-13 | 2012-01-10 | Fujifilm Corporation | Optical information recording medium, method of recording information, and azo metal complex dye |
| JP2009009684A (en) | 2007-06-01 | 2009-01-15 | Fujifilm Corp | Optical information recording medium and information recording method |
| JP5133284B2 (en) | 2008-09-25 | 2013-01-30 | 富士フイルム株式会社 | Optical information recording medium, information recording method, and azo metal complex dye |
| US20110202942A1 (en) | 2008-10-10 | 2011-08-18 | Fujifilm Corporation | Optical information recording medium, method of recording information and photosensitizer |
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2001
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| JP2002274040A (en) | 2002-09-25 |
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