JPS63303794A - Manufacture of optical recording medium - Google Patents
Manufacture of optical recording mediumInfo
- Publication number
- JPS63303794A JPS63303794A JP62140585A JP14058587A JPS63303794A JP S63303794 A JPS63303794 A JP S63303794A JP 62140585 A JP62140585 A JP 62140585A JP 14058587 A JP14058587 A JP 14058587A JP S63303794 A JPS63303794 A JP S63303794A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- coating
- optical 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.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000000758 substrate Substances 0.000 claims abstract description 36
- 239000011248 coating agent Substances 0.000 claims abstract description 31
- 238000000576 coating method Methods 0.000 claims abstract description 31
- 239000000243 solution Substances 0.000 claims abstract description 23
- 150000002576 ketones Chemical class 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- -1 ketone alcohol series Chemical class 0.000 claims abstract description 11
- 229920003023 plastic Polymers 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000004982 aromatic amines Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 150000002964 pentacenes Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 24
- 238000010521 absorption reaction Methods 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 11
- 239000004033 plastic Substances 0.000 abstract description 8
- 239000011521 glass Substances 0.000 abstract description 6
- 238000001746 injection moulding Methods 0.000 abstract description 5
- 230000002087 whitening effect Effects 0.000 abstract description 4
- 239000000113 methacrylic resin Substances 0.000 abstract description 3
- 239000004925 Acrylic resin Substances 0.000 abstract description 2
- 229920000178 Acrylic resin Polymers 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 22
- 239000000975 dye Substances 0.000 description 20
- 229920005668 polycarbonate resin Polymers 0.000 description 11
- 239000004431 polycarbonate resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000002991 molded plastic Substances 0.000 description 4
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- ZYKBEIDPRRYKKQ-UHFFFAOYSA-N 4-[4-(diethylamino)-2-methylphenyl]imino-1-oxo-n-phenylnaphthalene-2-carboxamide Chemical compound CC1=CC(N(CC)CC)=CC=C1N=C1C2=CC=CC=C2C(=O)C(C(=O)NC=2C=CC=CC=2)=C1 ZYKBEIDPRRYKKQ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- ORIHZIZPTZTNCU-VMPITWQZSA-N 2-[(E)-hydroxyiminomethyl]phenol Chemical compound O\N=C\C1=CC=CC=C1O ORIHZIZPTZTNCU-VMPITWQZSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000755266 Kathetostoma giganteum Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
- G11B7/2498—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds as cations
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
- G11B7/2472—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes cyanine
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/248—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes porphines; azaporphines, e.g. phthalocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Manufacturing Optical Record Carriers (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、光学記録媒体の製造方法に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a method for manufacturing an optical recording medium.
レーザーを用いた光学記録は、高密度の情報記録保存お
よび再生を可能とするため、近年、特に、開発が望まれ
ている。Optical recording using lasers has been particularly desired for development in recent years because it enables high-density information recording storage and reproduction.
光学記録の一例としては、光ディスクをあげる事ができ
る。特に、小型で信頼性が高く、安価な半導体レーザー
の出現に伴ない、コンパクトディスク（ＣＤ）等の貴生
専用型光ディスク、次いでＴｅ系無機材料を記録媒体と
する追記型光ディスクが実用化されてきた。これに対し
て、新しい追記型媒体としてレーザー吸収色素を用いた
有機色素系記録材料についても検討が行なわれており、
最大の特徴はスピンコード法等の塗布によシ成暎できる
ので、常圧での高生産性により将来のコストダウンの可
能性が期待されている。An example of optical recording is an optical disc. In particular, with the advent of small, highly reliable, and inexpensive semiconductor lasers, optical disks for exclusive use such as compact discs (CDs), and then write-once optical disks using Te-based inorganic materials as recording media have been put into practical use. . In response, studies are also being conducted on organic dye-based recording materials that use laser-absorbing dyes as new write-once media.
The most important feature is that it can be coated using a spin-coating method, so high productivity under normal pressure is expected to lead to future cost reductions.
一般に光ディスクは、円形の基板に設けられた薄い記録
層に、１μｍ８度に集束したレーザー光を照射し、高密
度の情報記録を行なうものである。In general, optical discs record high-density information by irradiating a thin recording layer provided on a circular substrate with a laser beam focused at 1 μm and 8 degrees.
記録は、照射され九レーザーエネルギーの吸収により、
その個所に生じた記録層の分解、蒸発、溶解等の熱的変
形により生成し、そして記録された情報の再生は、レー
ザー光により、変形が起きている部分と起きていない部
分の反射率の差を読み取る事によυ行なわれる。The recording is made by the absorption of nine laser energies that are irradiated.
The recorded information is generated by thermal deformation such as decomposition, evaporation, and melting of the recording layer that occurs at that location, and the recorded information is reproduced using a laser beam that changes the reflectance of the deformed part and the non-deformed part. This is done by reading the difference.
また、光ディスクの記録面には、正確な記録・再生を行
うため、案内溝があらかじめ形成されている。通常、こ
の案内溝はフォトポリマー法または射出成型法により形
成されるが、前者の場合、フォトポリマーから型取りす
るために生産性が悪く高価であるといり欠点を有してい
た。後者の場合は、射出成型法によるために生産性にす
ぐれ、安価なディスクを生産できるが、射出成型法に使
用できる樹脂は、加熱時の流動性が必要なため材料に制
約があり、一般に耐溶剤性が悪い。このような射出成型
プラスチック透明基板にレーザー吸収色素を溶液塗布に
よって薄膜形成させる場合、基板上の案内溝が塗布溶剤
におかされないことが必要であるが、塗布に使用できる
溶剤としては、これまでセルソルブ系溶剤が知られてい
るのみであった。（％願昭６Ｏ−２０６ｊＪＰ号）しか
も、セルソルブ系溶剤に高＃度に溶解するレーザー吸収
色素はほとんどなく、セルソルブ系溶剤は射出成型プラ
スチック基板に対する塗布溶剤として問題があっな。Furthermore, guide grooves are previously formed on the recording surface of the optical disc in order to perform accurate recording and reproduction. Usually, the guide groove is formed by a photopolymer method or an injection molding method, but the former method has disadvantages in that it is poor in productivity and expensive because it is molded from photopolymer. In the latter case, the injection molding method has excellent productivity and can produce inexpensive disks, but the resin that can be used for the injection molding method requires fluidity when heated, so there are restrictions on the material, and it generally has poor durability. Poor solvent properties. When forming a thin film of a laser-absorbing dye on such an injection-molded plastic transparent substrate by solution coating, it is necessary that the guide grooves on the substrate are not affected by the coating solvent. Only a series of solvents were known. (% Application No. 6O-206JJP) Furthermore, there are almost no laser-absorbing dyes that dissolve to a high degree in cellosolve solvents, and cellosolve solvents pose problems as coating solvents for injection molded plastic substrates.
そこで、射出成型プラスチック透明基板をおかすことな
く均一に塗布可能で、しかも、レーザー吸収色素を高ｅ
度に溶解する溶剤について鋭意検討した結果、ケトンア
ルコール系溶剤がその適性を有することを見い出し九。Therefore, it is possible to coat the injection-molded plastic transparent substrate uniformly without damaging it, and the laser-absorbing dye can be coated with a high e.g.
As a result of intensive research into solvents that dissolve the product, it was discovered that ketone alcohol-based solvents are suitable for this purpose.9.
本発明は、射出成型速切プラスチック基板をおかすこと
なく均一に塗布可能で、しかも、レーザー吸収色素を高
濃度にｆｆｊ解する溶剤を用いた光学記録媒体の製造方
法を提供することを目的とするものである。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for manufacturing an optical recording medium using a solvent that can be coated uniformly without damaging an injection-molded, quick-cut plastic substrate, and that dissolves a laser-absorbing dye in a high concentration. It is something.
本発明は、レーザー吸収色素の有機溶媒溶液を透明基板
上に塗布したのち乾燥して光学記録媒体を製造するに当
り、前記有機溶媒としてケトンアルコールを用いること
を特徴とする光学記録媒体の製造方法をその要旨とする
。The present invention provides a method for producing an optical recording medium, characterized in that ketone alcohol is used as the organic solvent in producing an optical recording medium by coating an organic solvent solution of a laser-absorbing dye on a transparent substrate and then drying the solution. The gist is:
本発明に使用する透明基板としては、ガラス、プラスチ
ック等が帛けられるが、種々の点からプラスチックが好
適である。プラスチックとしてはアクリル樹脂、メタア
クリル樹脂、酢酸ビニル樹脂、塩化ビニル樹脂、ニトロ
セルロース、ポリエチレン祷脂、ポリプロピレン樹脂、
ポリカーボネート樹脂、ポリイミド樹脂、ポリサルホン
樹脂等が挙げられる。The transparent substrate used in the present invention may be made of glass, plastic, etc., but plastic is preferable from various points of view. Plastics include acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin,
Examples include polycarbonate resin, polyimide resin, polysulfone resin, and the like.
特に好ましい透明基板としては、量産性にすぐれ、実用
的なレベルの複屈折、軟化点、耐熱性を有している射出
成型ポリカーボネート樹脂基板、ポリメタアクリル樹ｍ
基板が挙げられる。Particularly preferred transparent substrates include injection molded polycarbonate resin substrates and polymethacrylic resin substrates, which are easy to mass-produce and have practical levels of birefringence, softening point, and heat resistance.
Examples include substrates.
レーザー吸収色素としては、ケトンアルコール系溶剤に
高＋１度に溶解するものが挙げられ、ｔｏｏ〜りｏｏｎ
ｍの波長帯塚で吸収を有し、しかも分子吸収係数が１０
４〜ＩＯ”Ｃｌ１−”であるものが好適である。Examples of laser-absorbing dyes include those that are soluble in ketone alcohol solvents at a high degree of +1 degree.
It has absorption in the wavelength band m and has a molecular absorption coefficient of 10.
4 to IO"Cl1-" is preferred.
特に好ましいレーザー吸収色素としては、下記一般式（
１）、（Ｉｔ）、（ＩＩＩ）、〔ＩＶ〕で表わされる化
合物が挙げられる。Particularly preferable laser-absorbing dyes include the following general formula (
Examples include compounds represented by 1), (It), (III), and [IV].
一般式（１）
（式中、環ＡＩおよびＢｌは置換基を有していてもよい
ベンゼン環またはナフタレン環を表わし、Ｒ１およびＲ
２はｃ、 ｘ Ｃ，のアルキル基またはアルケニル基を
表わし、ｎ ＶｉＯ〜μの！５数を表わし、Ｘ−は陰イ
オンを表わす。）
一般式（ＩＩ）
Ｒ３、Ｒ４、Ｒ５、Ｈａ ｉｊ水Ｘ ＪｆＡ 子、７
ルキル某、７Ａ／コキシ基、アルコキシアルコキシ基、
ノーロメチル基又はハロゲン原子を示し、Ｒ７，Ｈａ
は水素原子又はハロゲン原子を示す。）
一般式（ＩＩＩ）
〔式中、Ｒ１１、Ｒ２Ｏのうちのいずれか−っは−〇（
Ｃ山０）ｐＨ１ｌ （式中、Ｒ１１は分枝していてもよ
いアルキル基を、ｐは／〜乙の数をそれぞれ表わす。）
であり、他の一つは水素原子であシ、Ａ３はＴｏ％Ｏｕ
、 Ｎｉ又は（！ｏで、ｉる。〕で示される化合物。General formula (1) (wherein, rings AI and Bl represent a benzene ring or a naphthalene ring which may have a substituent, R1 and R
2 represents an alkyl group or an alkenyl group of c, x C, and n ViO~μ! 5, and X- represents an anion. ) General formula (II) R3, R4, R5, Haij water X JfA child, 7
Rukyl, 7A/koxy group, alkoxyalkoxy group,
Indicates a noromethyl group or a halogen atom, R7, Ha
represents a hydrogen atom or a halogen atom. ) General formula (III) [wherein, any one of R11 and R2O -ha-〇(
C mountain 0) pH1l (In the formula, R11 represents an optionally branched alkyl group, and p represents the number of / to B, respectively.)
, the other one is a hydrogen atom, and A3 is To%Ou
, Ni or (!o, iru.).
一般式（ＩＶ）
（式中、ｙＦｉ金属原子を表わし、環Ａ４ 、 Ｂ！
は置換基を有していてもよい。Ｑは置換または非置換の
芳香族アミンの残基を表わし、２″″は陰イオンを表わ
す、）で示される含金属インドアニリン系化合物。General formula (IV) (wherein yFi represents a metal atom, rings A4, B!
may have a substituent. A metal-containing indoaniline compound represented by Q represents a substituted or unsubstituted aromatic amine residue, and 2'' represents an anion.
上叱一般式（１）、（Ｉｔ）、（１）、〔ＩＶ〕で示さ
れるレーザー液収色素において、環ＡＩおよびＢ２のベ
ンゼン環またはナフタレン環の置換基の例としては、フ
ッ″′Ｒ原子、塩素原子、臭素原子等のハロゲン原子、
メチル基、エチル基等のアルキル基、トリフルオロメチ
ル基等のハロゲン化アルキル基、メトキシ基、エトキシ
基等のアルコキシ基、メトキシエトキシ基等のアルコキ
シアルコキシ基、エトキシエチル基等のアルコキシアル
キル基等が挙げられる。Examples of substituents on the benzene ring or naphthalene ring of rings AI and B2 in the laser liquid absorbing dyes represented by general formulas (1), (It), (1), and [IV] include fluorine, atoms, halogen atoms such as chlorine atoms, bromine atoms,
Alkyl groups such as methyl group and ethyl group, halogenated alkyl groups such as trifluoromethyl group, alkoxy groups such as methoxy group and ethoxy group, alkoxyalkoxy groups such as methoxyethoxy group, alkoxyalkyl groups such as ethoxyethyl group, etc. Can be mentioned.
Ｒ１およびＲ３の０！〜Ｏｓのアルキル基としては、メ
チル基、エチル基、直鎖状または分校状のプロピル基、
メチル基、ペンチル基、ヘギシル基。0 for R1 and R3! The alkyl group of ~Os includes a methyl group, an ethyl group, a linear or branched propyl group,
Methyl group, pentyl group, hegysyl group.
ヘプチル基、オクチル基が挙げられ、アルケニル基とし
てはアリル基、λ−メチルアリル基、３−メチルアリル
基、λ−ブロモアリル基、３−プロモアリル基、λ−り
ｏ０アリル基、３−クｏａアリル基等が挙げられる。Examples include heptyl group and octyl group, and alkenyl groups include allyl group, λ-methylallyl group, 3-methylallyl group, λ-bromoallyl group, 3-promoallyl group, λ-rio0allyl group, 3-quaallyl group, etc. can be mentioned.
Ｘ−１２−の陰イオンとしては、ニー、Ｂｒ−１０１−
１ａ１ｏｎ、 Ｂｙ、％５ｏｘ−１ＯＨｓ（すＳＯ，−
、ｅｓＯｉ 。As the anion of X-12-, Ni, Br-101-
1a1on, By,%5ox-1OHs(SO,-
, esOi.
Ｒ３、Ｒ４、Ｈａ、Ｒ・ で示されるアルキル基として
は、メチル基、エチル基、直鎖状又は分岐状のプロピル
基、ブチル基、ペンチル基、ヘプチル基、ヘキシル基、
オクチル基等のＣ１〜８のアルキル基が挙げられる。ア
ルコキシ基としては、メトキシ基、エトキシ基、直鎖状
又は分岐状のプロポキシ基、ブトキシ基、ペンチルオキ
シ基、ヘプチルオキシ基、ヘキシルオキシ基、オクチル
オキシ基等の０１〜自のアルコキシ基が挙げらレル。ま
た、アルコキシアルコキシ基としては、メトキシエトキ
シ基、エトキシエトキシ基、メトキシプロポキシ基、ブ
トキシエトキシ基等が挙げられ、ハロメチル基としては
、クロロメチル基、ブロモメチル基等が挙げられる。ハ
ロゲン原子としては、フッ素原子、臭素原子、塩素原子
、ヨウ素原子が挙げられる。The alkyl group represented by R3, R4, Ha, R.
Examples include C1-8 alkyl groups such as octyl groups. Examples of the alkoxy group include methoxy, ethoxy, linear or branched propoxy, butoxy, pentyloxy, heptyloxy, hexyloxy, octyloxy, and other alkoxy groups. Rel. Examples of the alkoxyalkoxy group include a methoxyethoxy group, ethoxyethoxy group, methoxypropoxy group, butoxyethoxy group, and examples of the halomethyl group include a chloromethyl group and a bromomethyl group. Examples of the halogen atom include a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom.
また Ｒ７、Ｒａ で示されるハロゲン原子としては、
フッ素原子、臭素原子、塩素原子、ヨウ素原子が挙げら
れる。In addition, the halogen atoms represented by R7 and Ra are as follows:
Examples include fluorine atom, bromine atom, chlorine atom, and iodine atom.
また、Ｑ、′ｃ表わされる置換著しくは非置換の芳香族
アミンの残基としては、たとえばテトラヒドロキノリン
類、又は一般式
（式中 Ｒ１４及びＨｌｓはそれぞれ水素原子、ハロゲ
ン原子、アルキル基、アシルアミノ基、アルコキシ基、
アルキルスルホニルアミノ基又はアルコキシカルボニル
アミノ基を表わす。Ｒ” 及びＲ１３はそれぞれ、水素
原子、アルキル基、アリール基又はシクロヘキシル基を
表わし、そのアルキル基、アリール基又はシクロヘキシ
ル基は炭素数／〜２０であｐ１置換基として、たとえば
アルコキシ基、アルコキシアルコキシ基、アルコキシア
ルコキシアルコキシ基、アリルオキシ基、アリール基、
アリールオキシ基、シアノ基、ヒドロキシ基、テトラヒ
ドロフリル基等を有していてもよい）
で表わされる基があげられる。In addition, the substituted and significantly unsubstituted aromatic amine residues represented by Q and 'c are, for example, tetrahydroquinolines, or the general formula (wherein R14 and Hls are a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, respectively). , alkoxy group,
Represents an alkylsulfonylamino group or an alkoxycarbonylamino group. R" and R13 each represent a hydrogen atom, an alkyl group, an aryl group, or a cyclohexyl group, and the alkyl group, aryl group, or cyclohexyl group has a carbon number of 1 to 20 and is a p1 substituent, such as an alkoxy group or an alkoxyalkoxy group. , alkoxyalkoxyalkoxy group, allyloxy group, aryl group,
(which may have an aryloxy group, a cyano group, a hydroxy group, a tetrahydrofuryl group, etc.).
Ｍは■族、Ｉｂ族、■ｂ族、ｎｌａ族、ｌＶａ族、Ｖａ
族、Ｍａ族、■ａ族の金属原子が挙げられ、好ましくは
Ｎ１、Ｃｕ％ＣＯ金属原子が挙げられる。M is group ■, group Ib, group ■b, nla group, lVa group, Va
Examples include metal atoms of the Groups 1, 2, Ma, and 1a, preferably N1 and Cu%CO metal atoms.
環へ４、Ｂ３の置換基としては、水素原子、ハロゲン原
子、アルキル基、アルコキシ基、アシルアミノ基、アル
コキシカルボニルアミノ基、アルキルスルホニルアミノ
基が挙ケラレル。Examples of substituents on the ring 4 and B3 include a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acylamino group, an alkoxycarbonylamino group, and an alkylsulfonylamino group.
本発明方法による塗布による記録層の成膜は、上記一般
式〔１〕、（Ｉｌ〕、（ＩＩＩ）、〔ＩＶ〕で表わされ
るレーザー吸収色素をそのまｔあるいはバインダーとと
もにケトンアルコール系溶剤中に溶解させたものをスピ
ンコードすることＫより製造される。To form a recording layer by coating according to the method of the present invention, the laser-absorbing dyes represented by the above general formulas [1], (Il), (III), and [IV] are mixed directly or together with a binder in a ketone alcohol solvent. It is manufactured by spin-coding a melted product.
その際に使用するバインダーとしては、ケトンアルコー
ル系溶剤に溶解するものならば何でもよい。Any binder may be used as long as it dissolves in the ketone alcohol solvent.
本発明に使用するケトンアルコール系溶剤としては、通
常炭素数３〜７の脂肪族ケトンアルコール系溶剤が挙げ
られ、例えば下記のものが挙げられる。Examples of the ketone alcohol solvent used in the present invention include aliphatic ketone alcohol solvents having 3 to 7 carbon atoms, such as those shown below.
ａＨ。aH.
０Ｈ３０ａＦＩｓ Ｏ
Ｈ３
ＯＨ３ＯＣＨ３０
ＣＨｓ ＯＣＨ３０
これらのうち、好ましいものとしては、沸点７２０〜７
７０℃のもの、特にジアセトンアルコール、３−ヒドロ
キシ−３−メチル−λ−ブタノン等が挙げられる。0H30aFIs O H3 OH3OCH30 CHs OCH30 Among these, preferable ones have a boiling point of 720-7
Examples include those at 70°C, particularly diacetone alcohol, 3-hydroxy-3-methyl-λ-butanone, and the like.
ケトンアルコール系溶剤に対するレーザー吸収色素の比
率は０３〜３．０ｗｔ％が特に好ましい。The ratio of the laser-absorbing dye to the ketone alcohol solvent is particularly preferably 0.3 to 3.0 wt%.
また、バインダーに対するレーザー吸収色素の比率は１
０ｗｔ％以上が望ましい。Also, the ratio of laser-absorbing dye to binder is 1
0wt% or more is desirable.
色素を溶解させた溶液は０．Ｊμ以下のフィルターで濾
過することが好ましい。The solution in which the dye was dissolved was 0. It is preferable to filter with a filter of Jμ or less.
スピンコードの回転数は２００〜２００Ｏｒｐｍが好ま
しい。スピンコードの後、場合によっては加熱あるいは
溶媒蒸気にあてる等の処理を行なってもよい。The rotation speed of the spin cord is preferably 200 to 200 rpm. After the spin code, a treatment such as heating or exposure to solvent vapor may be performed depending on the case.
また、塗布膜の膜厚は、３００〜ｔｚｏｏＸが好ましい
。Further, the thickness of the coating film is preferably 300 to tzooX.
更に、記録媒体の安定性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嬌キレート化合物（アセチ
ルアセトナートキレート、ビスフェニルジチオール、サ
リチルアルデヒドオキシム、ビスジチオ−α−ジケトン
等）を含有していてもよい。Furthermore, it contains transition metal chelate compounds (acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-α-diketone, etc.) as a singlet oxygen quencher to improve the stability and light resistance of the recording medium. It's okay.
本発明の光学記ｆｊｋ媒体の配録層は基板の両面に設け
てもよいし、片面だけに設けてもよい。The recording layer of the optical recording FJK medium of the present invention may be provided on both sides of the substrate or only on one side.
上記の様にして得られ念記録媒体への記録は、基体の両
面または、片面に設けた記録層に／μｍ程度に集束した
レーザー光、好ましくは、半導体レーザーの光をあてる
事によシ行なう。レーザー光の照射された部分には、レ
ーザーエネルギーの吸収による、分解、蒸発、溶融等の
記録層の熱的変形が起こる。Recording on the optical recording medium obtained as described above is carried out by shining a laser beam, preferably a semiconductor laser beam, focused to about /μm onto the recording layer provided on both sides or one side of the substrate. . In the portion irradiated with the laser beam, thermal deformation of the recording layer such as decomposition, evaporation, and melting occurs due to absorption of laser energy.
記録され九情報の再生は、レーザー光により１熱的変形
が起きている部分と趨きていない部分の反射率の差を読
み取る事により行なう。The recorded information is reproduced by reading the difference in reflectance between a portion where thermal deformation has occurred and a portion where no thermal deformation has occurred using a laser beam.
光源としては、各種のレーザーを用いることができるが
、価格、大きさの点で、半導体レーザーが特に好ましい
。半導体レーザーとしては。Although various lasers can be used as the light source, semiconductor lasers are particularly preferred in terms of cost and size. As a semiconductor laser.
中心波長Ｉ Ｊ Ｏｎｍ 、中心波長７１０ ｎｍのレ
ーザーが望ましい。A laser with a center wavelength I J Onm and a center wavelength of 710 nm is desirable.
実施例
以下実施例によりこの発明を具体的に説明するが、かか
る実施例は本発明を限定するものではない。EXAMPLES The present invention will be specifically explained with reference to Examples below, but these Examples are not intended to limit the present invention.
実施例１
下記構造式
で表わされる含金属インドアニリン系化合物ｏ、ｉ ｓ
ｔを３−ヒドロキシ−３−メチルーコーブタノン１０
ｆに溶解し、０．２２μのフィルターで濾過し、溶解液
を得九。この溶液ｊ ｍｌを板厚／、２ｍのへ乙μｍピ
ッチの溝（グループ）つきポリカーボネート樹脂基板（
射出成型品５インチ）上に滴下し、スピナー法によ’９
１１００Ｏｒｐの回転数で塗布した。塗布後、６０℃で
ｉｏ分間乾燥した。塗布膜の最大吸収波長は第１図に示
すように７りｊ ｎｍであり、反射率はｓ ／ ％ （
Ｉ Ｊ Ｏｎｍ ）であった。Example 1 Metal-containing indoaniline compound o, is represented by the following structural formula
t is 3-hydroxy-3-methyl-cobutanone 10
f and filtered through a 0.22 μ filter to obtain a solution. Pour ml of this solution onto a polycarbonate resin substrate with grooves (groups) at a pitch of μm to a plate thickness of 2 m.
5 inch injection molded product) and spinner method.
Coating was carried out at a rotational speed of 1100 Orp. After coating, it was dried at 60° C. for io minutes. The maximum absorption wavelength of the coating film is 7 nm as shown in Figure 1, and the reflectance is s/% (
IJ Onm).
上記のように成膜した記録層を有する５インチの射出成
型ポリカーボネート樹脂基板を弘ｍ／ｅで回転させなが
ら、中心波長ｒ ３０ ｎｍの半導体レーザー光で、パ
ルス幅２００ ｎ５ｅｃで照射したところ、出力４ ｍ
Ｗで０／Ｎ比ｊ Ｊ ａＢを得た。保存安定性（４０℃
、１０％Ｒ）Ｉ）も良好であった。When a 5-inch injection-molded polycarbonate resin substrate having a recording layer formed as described above was irradiated with a semiconductor laser beam having a center wavelength of 30 nm and a pulse width of 200 n5ec while rotating at Hiromu m/e, the output 4 m
The 0/N ratio j J aB was obtained with W. Storage stability (40℃
, 10%R)I) were also good.
実施例コ
下記構造式
で表わされる含金属インドアニリン系化合物０、ｌ ｊ
ｔをジアセトンアルコール１０ｆに溶解し、０．２２
μのフィルターで濾過し、溶解液を得た。この溶液ｊ
ｍｌを板厚１．コ簡の／、４μｍピッチの溝（グループ
）つきポリカーボネート樹脂基板（射出成型品、３イン
チ）上に滴下し、スピナー法によりｒ ００ ｒｐｍの
回転数で塗布した。塗布後、６０℃で１，０分間乾燥し
た。塗布膜の最大吸収波長は第２図に示すようにｒｏｔ
ｎｍであシ、反射率は３７％（Ｉ Ｊ Ｏｎｍ ）であ
っ九。Example: Metal-containing indoaniline compound represented by the following structural formula 0, l j
Dissolve t in diacetone alcohol 10f, 0.22
The solution was filtered through a μ filter to obtain a solution. This solution j
ml is plate thickness 1. The mixture was dropped onto a polycarbonate resin substrate (injection molded, 3 inches) with grooves (groups) at a pitch of 4 μm and coated using a spinner at a rotation speed of r 00 rpm. After coating, it was dried at 60°C for 1.0 minutes. The maximum absorption wavelength of the coating film is rot as shown in Figure 2.
The reflectance was 37% (I J Onm ).
上記記録層を成膜した５インチのポリカーボネート樹脂
基板を参ｍ／θで回転させながら、中心波長１ ｊ Ｏ
ｎｍの半導体レーザー光でパルス幅ｊ ００ ｎ５ｅｃ
で照射したところ、出力ｔ ｍＷでａ／ｎ比ｊ参ｄＢを
得た。保存安定性（Ａ７７℃、１０チＲＨ）も良好であ
った。While rotating the 5-inch polycarbonate resin substrate on which the above recording layer was formed at a reference m/θ, the central wavelength was 1 j O.
Pulse width j 00 n5ec with nm semiconductor laser light
When it was irradiated with 200 nm, an a/n ratio of 1 dB was obtained at an output of t mW. The storage stability (A77°C, 10°C RH) was also good.
比較例／−／〜２−２
実施例１で示される含金属インドアニリン系色素を用い
、本発明ケトンアルコール系溶剤以外の溶剤について、
色素の溶解性、射出成型ポリカーボネート透明基板への
影響〔白化、溝ダレの有無〕、塗布膜の結晶化を比較し
たところ、本発明の実施例の方が著しく優れていた。Comparative Example /-/~2-2 Using the metal-containing indoaniline dye shown in Example 1, using a solvent other than the ketone alcohol solvent of the present invention,
When the solubility of the dye, the effect on the injection-molded polycarbonate transparent substrate (whitening, presence or absence of groove sag), and the crystallization of the coating film were compared, the examples of the present invention were significantly superior.
！また、実施例コで示される含金属インドアニリン系色
素を用い同様の比較を行ったところ、本発明の実施例の
方が著しく優れていた。! Further, when a similar comparison was made using the metal-containing indoaniline dye shown in Example C, the Example of the present invention was significantly superior.
実施例３
上記式（Ｖ）で示される本発明のシアニン色素ｌ？を下
記構造式
％式％
で示されるケトンアルコール系溶剤ｊＯｆに溶鱗し、０
．２−２μのフィルターで一過し、溶解液を得九。この
溶液コＩｌ！／を、深さ７００ｋ、巾０．７μの溝（グ
ループ）つき射出成型ポリメタアクリル樹脂基板（／３
０ｗＩＩφ）上に滴下し、／コ００ ｒｐｍの回転数で
塗布した。塗布後、６０℃で７０分間乾燥した。膜厚測
定のため、同−東件でガラス板に塗布してα−ステップ
による膜厚測定したところ、／！ＯＯＡであった。Example 3 Cyanine dye of the present invention represented by the above formula (V) l? is melted in a ketone alcohol solvent jOf shown by the following structural formula %, and 0
．． Pass through a 2-2μ filter to obtain a lysate. This solution! / is an injection molded polymethacrylic resin substrate (/3
0wIIφ) and applied at a rotational speed of 00 rpm. After coating, it was dried at 60°C for 70 minutes. To measure the film thickness, we coated it on a glass plate at the same company and measured the film thickness using the α-step, and found that /! It was OOA.
塗布膜の最大吸収波長は７りｏ ｎｍでありピーりは巾
広かった。The maximum absorption wavelength of the coating film was 7 nm, and the peeling was wide.
この塗布膜Ｋ、中心波長ｔ Ｊ Ｏｎｍの牛導体レーザ
ー光を出力４ ｍＷでビーム径／ 、ａｍで照射した所
、巾約／ｐｒｙｓ、ビット長約２μｍの輪郭の極めて明
瞭な孔（ピット）が形成された。キャリヤーレベル／ノ
イズレベル（Ｃ／Ｎ ） 比は７．２ ｔｉＢであった
。保存安定性（／、０℃、ｔｏ％ＲＨ）も良好であり九
。When this coating film K was irradiated with a conductor laser beam with a center wavelength t J Onm and an output of 4 mW and a beam diameter of / am, very clear holes (pits) with a width of / prys and a bit length of about 2 μm were observed. Been formed. The carrier level/noise level (C/N) ratio was 7.2 tiB. Storage stability (/, 0°C, to%RH) is also good.
実施例蓼
上記式〔■〕に示す本発明のシアニン色素／１゜ニトロ
セルロース／、、ｔ ｆ （ダイセル化学社判、ＲＥＩ
−，２０）を下記構造式
で示されるケトンアルコール系溶剤ｊＱ２に溶解し、０
．２λμのフィルターで一過し、溶解液を得た。この溶
液をＪゴを深さｔＳＯＸ、巾０．７μの＃Ｉ＃（グルー
プ）つき射出成型ポリメタアクリル樹脂基板（／２０ｍ
φ）上に滴下し、／ ｊ ００ ｒｐｍの回転数で塗布
した。塗布後、６０℃で７０分間乾燥した。膜厚測定の
ために、同様な方法でガラス板に塗布し、α−ステップ
によシ測定した所、膜厚ｌコＯＯＡであった。Examples Cyanine dye of the present invention shown in the above formula [■] / 1° nitrocellulose /, t f (Daicel Chemical Co., Ltd., REI
-, 20) is dissolved in a ketone alcohol solvent jQ2 represented by the following structural formula, and 0
．． The mixture was passed through a 2λμ filter to obtain a lysate. This solution was applied to an injection molded polymethacrylic resin substrate with #I# (group) of depth tSOX and width 0.7μ (/20m
φ) and applied at a rotation speed of / j 00 rpm. After coating, it was dried at 60°C for 70 minutes. To measure the film thickness, the film was coated on a glass plate in the same manner and measured using an α-step, and the film thickness was l OOA.
塗布膜の最大吸収波長はＩ ２０ ｎｍであシ、ピーク
は巾広かった。The maximum absorption wavelength of the coating film was I 20 nm, and the peak was broad.
この塗布膜に、中心波長ｒ Ｊ Ｏｎｍの半導体レーザ
ー光を出力ｔ ｍＷでビーム径１μｍで照射した所、巾
約ｌμ展、ピッ）４％約λμｍの輪郭の極めて明瞭な孔
（ビット）が形成された。Ｃ／Ｎ比は！１ｄＢであった
。保存安定性（４０℃、１０％ＲＨ）も良好であった。When this coating film was irradiated with semiconductor laser light with a center wavelength of r J Onm and an output of t mW and a beam diameter of 1 μm, extremely clear holes (bits) with a width of about 1 μm and a width of about 4% λ μm were formed. It was done. What is the C/N ratio? It was 1 dB. Storage stability (40° C., 10% RH) was also good.
実施例ｊ
融点’、ｉｔｏ〜／ １１℃
分子吸光係数（ｇ） ： ｒ、２Ｘ ／ ｏ４マススペ
クトル：ｊ２Ｊ（Ｍゝ）
クロロホルム溶液中のλｍａｘニア４０ｎｍ上記一般式
〔■〕で表わされる色素／、Ｑ？を下記構造式
で表わされるケトンアルコール系溶剤ｌ０９Ｋ溶解し、
０，２２μｍのフィルターで一過し、溶解液を得た。こ
の溶液コｙａｌを、深さ７００ｋ。Example j Melting point', ito~/11℃ Molecular extinction coefficient (g): r, 2X/o4 Mass spectrum: j2J (Mゝ) λmax near 40 nm in chloroform solution Dye represented by the above general formula [■]/, Q? is dissolved in a ketone alcohol solvent 109K represented by the following structural formula,
The solution was passed through a 0.22 μm filter to obtain a solution. This solution was poured to a depth of 700k.
巾０．７μｍの紫外線硬化樹脂による溝（グループ）つ
きＰＭＭＡ樹脂基板（／コ０！φ）上に滴下し、スピナ
ー法によＦ） ／ ０００ ｒｐｍの回転数で塗布した
。塗布後、６０℃で１０分間乾燥した。同一条件でガラ
ス板に塗布して、クリステツブによる膜厚測定したとこ
ろ、ｒｏｏｐ、であった。塗布膜の最大吸収波長は７０
よｎｍであり、反射率は３３％（ｔ ｊ Ｏｎｍ ）で
あつた。スペクトルの形状は巾広かった。It was dropped onto a PMMA resin substrate (/co0!φ) with grooves (groups) made of ultraviolet curable resin having a width of 0.7 μm, and coated by a spinner method at a rotation speed of F)/000 rpm. After coating, it was dried at 60°C for 10 minutes. When the film was coated on a glass plate under the same conditions and the film thickness was measured using a crystal tube, it was found to be loop. The maximum absorption wavelength of the coating film is 70
The reflectance was 33% (t j Onm ). The shape of the spectrum was wide.
この塗布膜に、中心波長７１０ ｎｍの半導体レーザー
光を出力１． ｍＷでビーム径ｌμ鴇で照射した所、巾
約７μｍ１ピツト長約λμｍの輪郭の極めて明瞭なビッ
トが形成された。動特性評価でＣ／Ｎ比はｊ ／ ｄＢ
（ｒ ｍＷ ）と高く、保存安定性（６０℃、１０％
ＲＨ）も良好であっ九。A semiconductor laser beam with a center wavelength of 710 nm was applied to this coating film at an output of 1. When irradiated with a beam diameter of 1 μm at mW, a bit with a very clear outline and a width of about 7 μm and a pit length of about λ μm was formed. In dynamic characteristic evaluation, C/N ratio is j/dB
(rmW) and storage stability (60℃, 10%
RH) was also good.
実施例６
下記構造式
％式％
クロロホルム溶液中のλｍａＸ ： ７りｏ ｎｒｎマ
ススペクトル；６≠ｆｆ（Ｍ”）
融点：２７０〜２７ｊ”Ｃ
で表わされる色素／、Ｏｆを下記構造式％式％
で表わされるケトンアルコール系溶剤！０？に溶解し、
０．２２μｍのフィルターで濾過し、溶解液を得た。こ
の溶液２ ｍｌを、射出成型ポリカーボネート樹脂基板
（／３０ｗａφ）上に滴下し、スピナー法により／ ０
００ ｒｐｍの回転数で塗布した。塗４後、４０℃で１
０分間乾燥し喪。同一条件でガラス板に塗布して、タリ
ステップによる膜厚測定したところ、７ｚｏＸであっ九
。Example 6 The following structural formula % formula % λmax in chloroform solution: 7 ion nrn mass spectrum; 6≠ff (M”) Melting point: 270-27 A ketone alcohol solvent represented by! 0? dissolved in
The solution was filtered through a 0.22 μm filter to obtain a solution. 2 ml of this solution was dropped onto an injection-molded polycarbonate resin substrate (/30waφ), and the spinner method was applied to
Coating was carried out at a rotation speed of 0.00 rpm. After coating 4, 1 at 40℃
Dry for 0 minutes and mourn. When it was coated on a glass plate under the same conditions and the film thickness was measured using Talystep, the result was 7zoX.
得られた射は１成型ポリカーボネート樹脂基板の分光光
度計による最大吸収波長は７６０ ｎｍであシ、６００
〜ＷＯＯｎｍに巾広い吸収スペクトルを有し、近赤外線
を有効に吸収していることを示した。The maximum absorption wavelength measured by the spectrophotometer of the molded polycarbonate resin substrate was 760 nm, and the obtained radiation was 600 nm.
It has a broad absorption spectrum in the range of ~WOOnm, indicating that it effectively absorbs near-infrared rays.
この塗布膜に、中心波長ｆ ３０ ｎｍの半導体レーザ
ー光を出力４ ｍＷでビーム径１μｍで照射した所、ｄ
〕約１μｍ１ピット長約λμｍの輪郭の極めて明瞭なピ
ットが形成された。動特性評価でＯ／Ｎ比はｊ ＯｄＢ
と高く、保存安定性（６０℃、ｔｏｔｓＲＨ）も良好で
あ−）た。When this coating film was irradiated with semiconductor laser light with a center wavelength f 30 nm at an output of 4 mW and a beam diameter of 1 μm, d
] Very clearly defined pits of about 1 μm and pit length of about λ μm were formed. In the dynamic characteristic evaluation, the O/N ratio is j OdB
The storage stability (60° C., totsRH) was also good.
実施例７
上記構造式で示される化合物の光吸収物質を下記構造式
％式％）
で表わされるケトンアルコール系溶剤に溶解し、コチの
溶液を調製し、この溶液をスピンコード法（回転数／
０００ ｒｐｍ ）によりグループ付きの射出成型メタ
クリル樹脂基板上に塗布した。Example 7 A light-absorbing substance of the compound represented by the above structural formula is dissolved in a ketone alcohol solvent represented by the following structural formula (%) to prepare a flathead solution.
000 rpm) onto a grouped injection molded methacrylic resin substrate.
塗布された薄膜（記碌層）の最大吸収波長はｌ弘Ｏｎｒ
ｎであり、吸収ピークは巾広かった。The maximum absorption wavelength of the applied thin film (recording layer) is
n, and the absorption peak was broad.
この薄膜に、中心波長ｒ Ｊ Ｏｎｍのレーザー光を出
カーｍＷ、ビーム径約／μｍで照射したところ、巾約１
μｍ１ビット長さ約λμｍの輪郭の極めて明瞭な孔（ビ
ット）が形成され、そのときのキャリアレベル／ノイズ
レベル比（０／Ｎ比）はｊ ／ ｄＢであった。ま九、
その保存安定性は、温度１０℃、相対湿度１０％の恒温
・恒湿槽中でＩＯ日間保存した後の半導体レーザー光に
よる書き込み性能のキャリアレベル／ノイズレベル比（
０／Ｎ比）によると！／ｄＢであっ九。When this thin film was irradiated with a laser beam with a center wavelength r J Onm and an output power of mW and a beam diameter of about 1 μm, the width
A hole (bit) with a very clear outline of approximately λμm in length was formed, and the carrier level/noise level ratio (0/N ratio) at that time was j/dB. Maku,
Its storage stability is determined by the carrier level/noise level ratio (
According to 0/N ratio)! /dB.
実施例！
実施例１〜７に準じてレーザー吸収色素をケトンアルコ
ール系溶剤に溶解し、射出成型ポリカーボネート樹脂基
板上に塗布した。Example! According to Examples 1 to 7, a laser-absorbing dye was dissolved in a ketone alcohol solvent and applied onto an injection molded polycarbonate resin substrate.
これらの本発明の塗布膜の最大吸収波長を第１表に示す
。Table 1 shows the maximum absorption wavelengths of these coating films of the present invention.
これらは実施例７〜７と同様にケトンアルコール系溶剤
に高濃度に溶解し、射出成型ポリカーボネート透明基板
をおかす（白化、溝ダレ等）ことなく均一に塗布可能で
あシ、塗布時に結晶化もなく、得られ九塗布膜は保存安
定性もすぐれ、反射率が高く、高感度でＯ／Ｎ比も良好
であった。Similar to Examples 7 and 7, these are dissolved in a ketone alcohol solvent at high concentrations, and can be applied uniformly without damaging the injection-molded polycarbonate transparent substrate (whitening, groove sag, etc.), and do not crystallize during application. However, the obtained coating film had excellent storage stability, high reflectance, high sensitivity, and good O/N ratio.
本発明によれば、レーザー吸収色素を高濃度に溶解し、
射出成型プラスチック透明基板をおかす（白化、溝ダレ
等）ことなく均一に塗布可能であり、塗布時に結晶化も
なく、得られた塗布膜が保存安定性くすぐれ、反射率が
高く、高感度でＯ／Ｎ比も高い、光学記録媒体を製造す
ることが出来るので、本発明方法は工業的に極めて有用
である。According to the present invention, a laser-absorbing dye is dissolved at a high concentration,
It can be applied uniformly without damaging the injection-molded plastic transparent substrate (whitening, groove sagging, etc.), there is no crystallization during application, and the resulting coating film has excellent storage stability, high reflectance, high sensitivity, and O The method of the present invention is industrially extremely useful since it is possible to produce an optical recording medium with a high /N ratio.
第１図は、実施例１で得られ念射出成型ポリカーボネー
ト樹脂基板の分光光度計による光吸収特性を示し、第２
図は実施例λで得られた射出成型ポリカーボネート樹脂
基板の分光光度計による光吸収特性を示す。各図におい
て縦軸は吸光度（左側）、反射率（右側）、横軸は波長
である。FIG. 1 shows the light absorption characteristics measured by a spectrophotometer of the superinjection molded polycarbonate resin substrate obtained in Example 1, and
The figure shows the light absorption characteristics measured by a spectrophotometer of the injection molded polycarbonate resin substrate obtained in Example λ. In each figure, the vertical axis is absorbance (left side) and reflectance (right side), and the horizontal axis is wavelength.
Claims (3)
塗布したのち乾燥して光学記録媒体を製造するに当り、
前記有機溶媒として、ケトンアルコールを用いることを
特徴とする光学記録媒体の製造方法。(1) When manufacturing an optical recording medium by coating an organic solvent solution of a laser-absorbing dye on a transparent substrate and then drying it,
A method for producing an optical recording medium, characterized in that a ketone alcohol is used as the organic solvent.
ことを特徴とする特許請求の範囲第１項記載の製造方法
。(2) The manufacturing method according to claim 1, wherein the transparent substrate is an injection molded transparent plastic substrate.
、〔III〕又は〔IV〕で表わされる化合物であることを
特徴とする特許請求の範囲第１項又は第２項のいずれか
に記載の製造方法。 一般式〔 I 〕 ▲数式、化学式、表等があります▼・・・〔 I 〕 （式中、環Ａ＾１およびＢ＾１はベンゼン環またはナフ
タレン環を表わし、これらの環は置換基を有していても
よい。Ｒ＾１およびＲ＾２はＣ＿１〜Ｃ＿■のアルキル
基またはアルケニル基を表わし、これらの基は置換され
ていてもよい。ｎは０〜４の整数を表わし、Ｘ＾−は陰
イオンを表わす。）で示されるシアニン化合物。 一般式〔II〕 ▲数式、化学式、表等があります▼・・・〔II〕 （式中、Ａ＾２、Ｂ＾２は▲数式、化学式、表等があり
ます▼又は酸素原子を示し、Ｒ＾３、Ｒ＾４、Ｒ＾５、
Ｒ＾６は水素原子、アルキル基、アルコキシ基、アルコ
キシアルコキシ基、ハロメチル基又はハロゲン原子を示
し、Ｒ＾７、Ｒ＾８は水素原子又はハロゲン原子を示す
。）で示される９、１９−ジオキサジナフト−〔３、２
、１−ｄｅ；３、２、１−ＯＰ〕ペンタセン系誘導体。 一般式〔III〕 ▲数式、化学式、表等があります▼・・・〔III〕 〔式中、Ｒ＾９、Ｒ＾１＾０のうちのいずれか一つは−
Ｏ（Ｏ＿２Ｈ＿４Ｏ）＿ｐＲ＾１＾１（式中、Ｒ＾１＾
ｌは分枝していてもよいアルキル基を、ｐは１〜６の数
をそ れぞれ表わす。）であり、他の一つは水素 原子であり、Ａ＾３はＶＯ、Ｃｕ、Ｎｉ又はＣｏである
。〕 で示される化合物。 一般式〔IV〕 ▲数式、化学式、表等があります▼・・・〔IV〕 （式中、Ｍは金属原子を表わし、環Ａ＾４、Ｂ＾３は置
換基を有していてもよい。Ｑは置換または非置換の芳香
族アミンの残基を表わし、Ｚ＾−は陰イオンを表わす。 ）で示される含金属インドアニリン系化合物。(3) The laser-absorbing dye has the following general formula [I], [II]
, [III] or [IV]. General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼...[I] (In the formula, rings A^1 and B^1 represent a benzene ring or a naphthalene ring, and these rings have substituents. R^1 and R^2 represent an alkyl group or an alkenyl group of C_1 to C_■, and these groups may be substituted. n represents an integer of 0 to 4, and X^ A cyanine compound represented by - represents an anion. General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[II] (In the formula, A^2, B^2 are ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or represent an oxygen atom, R ^3, R^4, R^5,
R^6 represents a hydrogen atom, an alkyl group, an alkoxy group, an alkoxyalkoxy group, a halomethyl group, or a halogen atom, and R^7 and R^8 represent a hydrogen atom or a halogen atom. ) 9,19-dioxazinaphtho-[3,2
, 1-de; 3, 2, 1-OP] pentacene derivative. General formula [III] ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[III] [In the formula, one of R^9 and R^1^0 is -
O(O_2H_4O)_pR^1^1 (in the formula, R^1^
l represents an optionally branched alkyl group, and p represents a number from 1 to 6, respectively. ), the other one is a hydrogen atom, and A^3 is VO, Cu, Ni or Co. ] A compound represented by General formula [IV] ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[IV] (In the formula, M represents a metal atom, and rings A^4 and B^3 may have substituents. .Q represents a substituted or unsubstituted aromatic amine residue, and Z^- represents an anion).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62140585A JP2552671B2 (en) | 1987-06-04 | 1987-06-04 | Method for manufacturing optical recording medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62140585A JP2552671B2 (en) | 1987-06-04 | 1987-06-04 | Method for manufacturing optical recording medium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63303794A true JPS63303794A (en) | 1988-12-12 |
| JP2552671B2 JP2552671B2 (en) | 1996-11-13 |
Family
ID=15272114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62140585A Expired - Lifetime JP2552671B2 (en) | 1987-06-04 | 1987-06-04 | Method for manufacturing optical recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2552671B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218072B1 (en) * | 1997-11-20 | 2001-04-17 | Taiyo Yuden Co., Ltd. | Optical information recording medium |
-
1987
- 1987-06-04 JP JP62140585A patent/JP2552671B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218072B1 (en) * | 1997-11-20 | 2001-04-17 | Taiyo Yuden Co., Ltd. | Optical information recording medium |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2552671B2 (en) | 1996-11-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH03268994A (en) | Optical recording material | |
| JPH0764992B2 (en) | Metal-containing indoaniline compounds | |
| JPS63303794A (en) | Manufacture of optical recording medium | |
| JP2685054B2 (en) | Naphthoquinone methide compounds | |
| JP3673963B2 (en) | Optical information recording medium | |
| JP3168469B2 (en) | Optical recording medium | |
| JP2002212454A (en) | Cyanine pigment | |
| JP2835526B2 (en) | Manufacturing method of optical recording medium | |
| JP2946665B2 (en) | Manufacturing method of optical recording medium | |
| US7316890B2 (en) | Indolestyryl compound for use in recording media and method for fabrication thereof | |
| JPH0446186A (en) | Azo metal chelate compound and optical recording medium using the same compound | |
| JPH0386583A (en) | Preparation of optical recording medium | |
| JPH11170695A (en) | Optical recording material | |
| JPH1134497A (en) | Optical recording medium | |
| JP2993117B2 (en) | Metal chelate compound and optical recording medium using the compound | |
| JPS6267068A (en) | Cyanine compound and optical recording medium | |
| JP2600763B2 (en) | Metal-containing compound and optical recording medium using the compound | |
| JP3064373B2 (en) | Metal chelate compound and optical recording medium using the compound | |
| TWI339397B (en) | Optical recording medium and method for manufacturing the same | |
| JP4051303B2 (en) | Optical recording medium and manufacturing method thereof | |
| JP2890407B2 (en) | Optical recording medium | |
| JPH02568A (en) | Optical recording medium | |
| JPH0280466A (en) | Azulene compound | |
| JPS60150241A (en) | Optical recording medium and its manufacture | |
| JPH01130986A (en) | Optical recording medium |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| EXPY | Cancellation because of completion of term | ||
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20070822 Year of fee payment: 11 |