TW589349B - New indolestyryl compounds and its use for a high density optical recording medium - Google Patents

New indolestyryl compounds and its use for a high density optical recording medium Download PDF

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TW589349B
TW589349B TW091108158A TW91108158A TW589349B TW 589349 B TW589349 B TW 589349B TW 091108158 A TW091108158 A TW 091108158A TW 91108158 A TW91108158 A TW 91108158A TW 589349 B TW589349 B TW 589349B
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Shin-Shin Wang
Wen-Yih Liao
Chii-Chang Lai
Chien-Liang Huang
Hui-Ping Tsai
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Ind Tech Res Inst
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Priority to US10/242,416 priority patent/US6815031B2/en
Priority to JP2002277031A priority patent/JP3961385B2/ja
Priority to DE10249654A priority patent/DE10249654B4/de
Priority to KR10-2003-0024366A priority patent/KR100528709B1/ko
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242Record 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
    • G11B7/244Record 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
    • G11B7/246Record 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
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/2403Layers; Shape, structure or physical properties thereof
    • G11B7/24035Recording layers
    • G11B7/24038Multiple laminated recording layers
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
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    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
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    • G11B7/253Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
    • G11B7/2534Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
    • G11B7/2535Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polyesters, e.g. PET, PETG or PEN
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
    • G11B7/2538Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycycloolefins [PCO]
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/258Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers
    • G11B7/2585Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers based on aluminium
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/258Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers
    • G11B7/259Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers based on silver
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording 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
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/258Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers
    • G11B7/2595Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of reflective layers based on gold
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/21Circular sheet or circular blank

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Indole Compounds (AREA)
  • Manufacturing Optical Record Carriers (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

589349 修正
案號 91108158 五、發明說明(1) 【發明的應用範圍】 本發明是關於一種新型吲哚苯乙烯鹽化合物 (indolestyryl compounds),特別是關於一種新型吲哚笨 乙烯鹽化合物及使用其於高密度記錄媒體。 【發明的背景】 隨著資訊與多媒體世代的來臨,包括電腦、通訊、消 費性電子之3C(Computer,Communication,Consumer
Electronics)產品對於儲存媒體的儲存密度及容量之需 ^不斷的增加。由於大量資訊的流通,f要儲存密度/ 间、更小型化,而製作成本更低的儲存媒體。一般之磁 體已:敷所需,❿高密度的光資訊儲存媒體正是研 九開叙的目標。就光資訊儲存媒體而言,目前有一些 ,記錄密度的原理及方法已被提出, :射長’例如將雷射光源由紅光“改;藍= 攸訊號編碼的方式戋用所二田如紗^ 良數 錄方式。以上的方法皆能有效提高儲存穷产。 韦。己 此外,光資訊儲存媒#另一古品—山又 光記錄層所使用之有機染料另開;= 標則為改變 ό_。近幾年來,由於』寫=型 記錄層有機染料也成為爭相開=點相 589349
向於飽和的狀悲 η〜/嗯、展耐入$ > 體如記憶容量可達4.7GB之僅芎\二在度的資訊儲存媒 (Dlgltal VersatlleDlsc)^使— 用次/=^ 光碟片 的重點。由於高密度儲存媒!# 成為目月j研九 a丄 如MD-R光碟片所传用之φ 射波長為65 0nm與CD-R光碟片所祐田七不6々尸^便用之田 π 、,&执、九μ &、+ u 所使用之雷射波長780nm不 同,乂致於木料…、法/、用,所以重新設 媒體所使用之記錄層有機毕料則士、炎去西』知河⑴度保存 日α紙木料則成為重要的發展目標。 【發明之目的與概述】 本發明的目的在於提供一種新型卩引卩朵苯乙烯鹽化合物 (mdolestyryl c⑽pounds)以及使用其於高密度可錄 碟片。其新型吲哚苯乙烯鹽化合物(ind〇lestyryi compounds)的特性為在波長為在5〇〇奈米至7〇〇奈米之間 (、λ= 5 0 0nm〜70 0nm)的可見光區有極大吸收,且具有高敏 感度及對於光和熱的化學穩定性,以及對有機溶劑具有良 好的溶解性。 ^ 义 為達上述目的,本發明所提供一種新型卩引卩朵笨乙烯鹽 化合物(indolestyryl compounds),係具有化學式(I)之 結構,以圖示方式表示如下··
R2 /
N \ R3
第10頁 589349 案號 91108158 曰 修正 五、發明說明(3) ' 其化學式結構如(I),R1、R2、R3、R4、R5和Υ-則分別代 表連接化學式結構不同位置之基團。其中當R1為苯環酯基 團(CH2C6H4C02R6)、直鏈烷磺酸酯基(CH2)nS03R6或直鏈烷酯 基(CH2)nC02R6 ; Y-可為四氰基-對奎諾二曱烷(TCNQ-, teteacyano-p-quinodi methane)、四氰乙烯(TCNE_ , tetracyanoethyl.ene)、過氯酸根(C104-)、六氟銻酸鹽 (SbF6-)、六氟磷酸鹽(PF6_)、四氟硼酸鹽(BF4-)和鹵素離子 (Γ)其中之一。
而R2、R3為相同或不同之基團,可分別為氫原子、含1 至8個碳((V8)之烷基、含1至8個破(Ch )之烧氧基及含1至8 個破(Cu )之烷酯基(-C02 R6 )其中之一;以及,R2和R3亦可 相連形成含氮雜環。 R4和R5為相同或不同之基團,可分別為氫原子、含1至 8個碳(Cm )之烷基、三氟曱基、烷氧基、羧基、硝基、醯 胺基(C0NR7R8)、磺酸基、磺酸酯基(S03R9)、含1至8個碳之 烷酯基和鹵素原子(X-)族群其中之一。 . 此外,Y-的選擇需要配合R1為含1至8個碳(Ch)之 烷基時,Y-需選擇TCNQ-(teteacyano-p-quinodimethane)
和TCNE—( tetracyanoety 1 ene)其中之一;另夕卜,當R1選擇 苯環酯基團(CH2C6H4C02R6)、直鏈烷磺酸酯基(CH2)nS03R7及 直鏈烷酯基(CH2)nC02R7其中之一時,Y-可選擇為四氰基-對 奎諾二甲烧(TCNQ-,teteacyan〇-p-quinodimethane)、四 氰乙稀(TCNE— ,tetracyan〇ethylene)、過氯酸根 (C104-)、六氟銻酸鹽(SbF6—)、六氟磷酸鹽(PF6—)、四氟硼
第11頁 589349 --------------- 木號 91108158 年 月_g_修正_ 五、發明說明(4) " 酸鹽(BF4)和鹵素離子其中之一。 ▲應用於新型问丨噪苯乙烯鹽化合物(indolestyryl compounds)之化學式的R1為直鏈烷酯基(CD/% R6、直鏈 烷磺酸酯基(CH2)nS〇3 R6與苯環酯基團(CH2C6H5C02R6)時,R6 可為含1至8個碳之烷基或氟烷基((:2;ρ4,cf3)。 當新型卩引哚苯乙烯鹽化合物之化學式的R4和巧為匕^之 烷酯基(-C〇2;R6 )時,R6可為含}至8個碳之烷基或氟烷基 (C2F4,CF3); R4和R5若為醯胺基(_c〇NR7R8)時,^和以可 為相同或是不同的基團,其中R?和^可為氫原子或含丨至6 個碳之烷基;如R4和R5為磺酸酯基(-SO# )時,R9可為气 原子或含1至6個破之烧基。上述基團的選擇可分別適用於 化學式(I )中。 ' 此外,本發明之新型吲哚苯乙烯鹽化合物的製造方 法,其製造方法需要進行化合物(11)與化合物(111)的偶 合反應,在有機溶劑的環境下合成吲哚苯乙烯鹽化合物 (i ndo1estyry 1 compounds)。 本發明之新型吲哚苯乙烯鹽化合物的製造方法為·· 將化合物(I I )與化合物(Π I )在有機溶劑的環''境下 進行偶合反應即可得到帶鹵素離子(X-)之吲哚苯乙烯_化 合物(IV) : ^
第12頁 589349 案號91108158 年月日 修正
第13頁 589349 -案號?niflSIRR 五、發明說明(6) 本發明的目的在於 合物染料之高密度資訊 口引哄笨乙烯鹽化合物染 層。由於此新型吲哚苯 所以相較於一般應用於 4貝格較為低廉,可以達 之應用新型吲哚苯乙浠 體具有良好的光敏感度 性0 曰 本發明另 作為可錄式光 其包含有:第 層,該記錄層 弟一基板表面 板,係為具有 第二基板即形 度可錄式光碟 苯乙烯鹽化合 新型吲噪苯乙 7 〇 〇奈米之間( 且具有高敏感 溶劑具有良好 有關本發 詳細說明如下 有一目的 碟片的記 一基板, 係由新型 ;以及配 溝槽的透 成使用新 片。其中 物作為形 稀鹽化合 λ 二 5 0 0nm 度及對於 的溶解性 明的特徵 修正 &供一種應用新型卩引卩朵苯乙稀鹽化 儲存媒體,本發明係利用一種新型 料形成高密度資訊儲存媒體的記錄 乙稀鹽化合物合貪容易且易純化, 高密度資訊儲存媒體染料之化合物 到降低成本的功效。此外,本發明 鹽化合物染料之高密度資訊儲存媒 ’且其記錄層具有極佳的化學穩定 ,係使用新型吲哚苯乙烯鹽化合物 錄層以形成高密度可錄式光碟片, 係為具有溝槽的透明基板;記錄 13引卩朵苯乙稀鹽化合物染料所形成於 置於記錄層上的反射層;第二基 明基板,再以貼合層貼合反射層與 型卩引卩朵苯乙烯鹽化合物染料之高密 ,本發明的特點在於應用新型吲哚 成記錄層的染料。本發明所使用之 物,其特性在於波長在5 0 0奈米至 〜700nm)的可見光區有極大吸收, 光和熱的化學穩定性,以及對有機 〇 與實作,茲配合圖示作最佳實施例
第14頁 — 589349
【較佳實施例說明】 > 明係揭路一種新型口引D朵苯乙烯鹽化合物及使用其 於咼捃度課錄式光碟片。本發明之新型吲哚苯乙烯鹽化合 物,係具有如上述之具有化學式(1)之結構。並且可配合 不同之基團加以組合Ό 為了進一步說明本發明,本發明列舉其實施例的合成 步驟及其化學式。以合成具有化學式⑴之新型化合物為 例其化本式(I )的結構通式如發明内容所述。 本發明之第一實施例為將5克起始物(丨丨)其R1為 及2.4克(111)其1^、1?3為相同之(—(:2][15),溶解於12(^1乙 醇中,並加熱至乙醇的回流溫度反應丨丨小時;待反應完 後,經過濾烘乾可得綠色固體結晶(A),其化學式為 (I V),其中之R4和R5為氫原子,X-為碘離子,反應產率 83%。經物性分析後,測得化合物(A)之吸收波長為566奈 米(UVmaX = 5 6 6nm)。再將化合物(A)與不同的鋰、鈉和鉀離 子化合物其中之一在有機溶劑中下進行離子交換反應,即 可形成多種具有化學式(I )的新型化合物。以下列舉化合 物(A)舆不同化合物進行的離子交換反應所合成的新型化 合物製作流程以及其性質: (1 )取化合物(A)之固體結晶2· 84克與六氟銻酸鈉(NaSbF6) 1 · 5克溶於5 0笔升(m 1 )的乙醇中,並加熱回流以進行離子 置換’待反應完後經過遽烘乾可得深綠色固體結晶之化合
第15頁 589349 _tS-,,9jl〇8158__年月 η 倏正 五、發明說明(8) 物(Β,化學式I,R4與R5二H,Y- = SbF6-),.經計算其反應產率 89%,經物性分析後,測得化合物(B)之吸收波長為5 66奈 米(UVmax = 5 6 6nm),吸收係數(ε)= 1〇9 χ 1〇5。 (2) 取化合物(Α)之固體結晶2.84克與LiTCNQ 1·6克溶於50 毫升(m 1)的乙傳中,並加熱產生回流以進行離子置換,待 反應完後經過濾烘乾可得金黃綠色固體結晶之化合物(c, 化學式I,R4、R5 = H,Y = TCNQ〇,經計算其反應產率86%,經 物性分析後’測得化合物(C)之吸收波長為5 6 6奈米 (UVmax=566nm) ° 本發明之第二實施例同樣為合成具有化學式(丨)的新 型化合物,其中側基R1係選擇—(CH2)4C〇2CH3。將9克之具有 化學式(II )的化合物作為起始物,其R1為―(CH2)4C〇2CH3& 4 · 3克具有化學式(11 I )的化合物其r2、r3為相連成含氮雜 環之,溶解於1 0 〇耄升乙醇中,並加熱至乙醇的回流溫 度反應11小日守;待反應完後’經過濾烘乾可得綠色固體結 晶之化合物(G ’化學式IV,R4、R5= ,其反應產率 8 6 %。經物性分析後。測得化合物(g )之吸收波長為5 5 7奈 米(UVmax = 5 5 7nm)。再將化合物(G)與不同的鋰、鈉和鉀之 離子化合物其中之一在有機溶劑中下進行離子交換反應, 即可形成多種具有化學式(I )的新型化合物。以下列舉化 合物(G)與不同化合物進行的離子交換反應所合成的新型 化合物的製作流程以及其性質: (3) 取化合物(G)之固體結晶2. 5克與六氟銻酸鈉(NaSbF6 ) 1 · 4克溶於5 0毫升(m 1)的乙醇中,並加熱回流以進行離子
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案號 91108158 五、發明說明(9) 置換’待反應完後經過、声卜 物(H,化學式I,R4、: ‘可得深綠色固體結晶之化合 93% ’經物性分析後,测得化人D ’ =計算其反應產率 米(UVmax二557nm)。 〇物(H)之吸收波長為55 7奈 其中,本發明之第一余 卜 合物(A)與⑹係為具有硬;施例所形成之化 後再與各種鋰、鈉和卸趟 =引0木本乙烯鹽化合物。然 置換。待反應完後經過合物:有機溶劑中進行離子 乙烯鹽化合物(B)、( c) Γ f n /即可彳于本發明之新型吲哚苯 ⑴。將各新型化合物之二、⑻、⑴和 式表示,如表一所示: 式/、取大吸收波長以表格方 表—為_苯乙烯鹽化合物之化學式及最大吸收波長
第17頁 589349 _案號91108158_年月日 修正 五、發明說明(10) D ; 566 9.82x1 04 I E ^〇^。\ . 568 1 編· M 丨· i-c>>-〇-〇 NX。、 〇 \ 567 8.78xl04 1 G [ F , .(ch2)4c〇2c2h5 557 6.72x104 ϊ |h (CH2)4C〇2C2H5 557 --- I 1 c4h9 555 7.52xl04 j (CH2)4S〇3CH3 556 6.35xl04 第18頁 589349
I 曰 五、發明說明(11) πΪ Ϊ ^明貫施例所得之新型吲哚苯乙烯鹽化合物,再 稀釋和處理的步驟,#可應用於高密度光碟片 =1::ί:以透過混和一種以上之新型吲哚苯乙烯鹽化 合物來传到南密度光碟片染料所需的性質。 ϋ >更進步將新型吲哚苯乙烯鹽化合物使用於高密度可 碟片,記錄層。請參考第1圖,第1圖為使用新型 口引D朵本乙烯鹽化合你逃粗 > + 物木抖之鬲逾、度可錄式光碟片的應用實 施例不思圖,包含有··一第一基板10,係為透明基板;二 €錄層’記錄層20係由新型吲哚苯乙烯鹽化合物染料所 形成於第一基板10表面;以及配置於記錄層2〇上的反射層 30,反射層30並塗佈有樹脂保護層4〇 ;第二基板⑽,係^ 透明基板;及-貼合層,貼合層5〇係用於貼 40與第二基板60。 卞更智 其中,配合本發明所使用之新型吲哚苯乙烯鹽化合 物,係具有如前述的化學式(丨)之結構,並且可配合不同 之離子基團加以組合。使用新型吲哚苯乙烯鹽化合物染料 於南密度可錄式光碟片的材料選擇及其製法可由本發明廡 用實施例之製程步驟得知。 Χ μ 以下為本發明應用實施例之製程步驟,其步驟包含 有: 首先,取新型吲哚苯乙烯鹽化合物丨.8 g溶於2,2,3,3 一 四氟丙醇(2,2,3,3-tetrafluor〇pr〇pan〇i)中,並配掣 成100g的溶液’·再將此溶液利用塗佈方式,塗佈於第一&基
板1 0上;然後進行供齡制夺 〇Η[ ρψ ^ r gs /V ^ 、 土板表面形成一層新型 引木本乙烯鹽化合物之記錚芦2 n · 姑枓L7彤士、G u綠層ZU,於兄錄層20上濺鍍金屬 材枓以开> 成反射層3 〇,麸德至泠此L „ .^ ^ _ …、後再塗佈上一層樹脂保護層40 ; 取後k供一弟二基板,祐脾笙-使> u ㈣爲…士艾基板利用一貼合層與樹脂 保叹層40…,即完成一高密度可錄式光碟片。 上述之第一基板與第二基板為一具有溝執(land)及溝 槽(groove)之透明基板,其軌距(track pUch)為〇·3微
米至0.8微米(mm),溝深(Gr〇〇ve心“…為”奈米至2⑽奈 米(nm);基板材質可為聚酯類、聚碳酸酯類 (Polycarbonat,PC)、聚烯類等(PMMA、MC〇c)。 其記錄層形成方式,可透過旋轉塗佈、真空蒸鍍、喷 佈、滚壓塗佈或含浸等方式,其中以旋轉塗佈方式為最 佳’形成之記錄層膜厚為以70奈米至25〇奈米(nm)為最 佳0
塗佈用之有機溶劑可為含1至6個碳的醇類 (alcohol)、含1至6個碳酮類(ketone)、含1至6個碳 醚類(ether)、鹵素化合物環烷類及醯胺(amide)其中 之一。其中,醇類可為曱醇(methanol)、乙醇 (ethanol )、異丙酉享(isopropanol)、二丙酉同酉享 (diacetonalchol ; DAA ) 、2, 2, 3, 3-四氟丙醇 (2, 2, 3, 3-tetrafluoropropanol )、三氯乙醇 (trichloroethanol) 、2-氯乙醇(2-ch 1 oroethano1 )、人氣戍酉享(octafluoropentanol )、 或六氟丁醇(hexaf luorobutanol );酮類可為丙酮 (acetone)、甲基異丁 _ (methyl isobutyl ketone ;
第20頁 589349 _ 案號91108158_年月曰 修正____ 五、發明說明(13) MIBK )、甲基乙基酮(methyl ethyl ketone, MEK )、或 3-經基-3-甲基-2 - 丁酮(3-hydr〇xy-3-methyl-2-butanone);鹵素化合物可為氯仿(chloroform)、二氯 甲烧(dichloromethane)、或 1-氯丁烧(1-chlorobufane );醯胺可為二甲基曱醯胺 (dimethyl formamide, DMF )、或二甲基乙 ϊ篮胺 (dimethylacetamide,DMA );環烷類為曱基環己烷 (Methylcyclohexane , MCH) 〇 此外,濺鍍於記憶層上之反射層材質可為金、銀、
鋁、矽、銅、銀鈦合金、銀鉻、銀銅等金屬或其合金材 料’貼合弟一基板與弟一基板的方式可利用旋轉塗佈法、 網印、熱融膠法、雙面膠帶貼合法等。
本發明之實施例所形成於基板上的記錄層之厚度約為 70奈米至250奈米(nm),緊接著在記錄層上鍍一層厚度 約50奈米至2 0 0奈米(nm)之反射層;最後將具有反射層及 。己1:¾層的基板與另一片厚度為〇. 6 m m之空白基板貼合起來 (貼合方式可以是旋轉塗佈法、網印法、熱融膠法及雙面 膠帶貼合法等等),即成為—片厚度為12〇麗之高密度可 T式光碟片。第2圖為本發明之應用實施例的高密度可錄 ^光碟片反射率對波長之光譜圖,^圖所#,在波長 為635奈米(nm)以及65〇奈米(nm)下,其反射率均可大於 DDU_
第21頁 589349 ___案號91108B8_年月日__ 五、發明說明(14) " ^^^ 其寫錄條件如下:常線速度(Constant Linear Velocity ;CLV)為3·5 (公尺/秒)m/s、波長為6 5 8奈米 (nm)、數值半徑(Numerical Aperture ; ΝΑ)為 0.6、寫 錄功率為7〜14毫瓦(mW)。 ' 讀取條件如下:常線速度(CLV)為3·5(公尺/秒) m/s、波長為6 58奈米(nm)、數值半徑(ΝΑ )為〇· 6、讀取 功率為0· 5〜1· 5毫瓦(mW)。 表二即為本發明實施例在不同寫錄功率下的CNR值。 表^一 · 寫錄功率 (mW) 7 8 9 10 11 12 .13 14 ;3T CNR [(dB) 39.0. 44.5 50.2 55.5 57.2 58.9 59.2 _ ------ 59.2 ------------------- 由表二可看出當寫錄功率在9mW以上時,其CNR值均。 大於5 0 dB。表示本發明實際應用例所製作出之高密度光 碟片具有高敏感度、光與熱之化學穩定性等優點。 【發明功效】 本發明揭露之新型吲哚苯乙烯鹽化合物 (indolestyryl compounds),具有合成容易以及容易純 的特點。此外,本發明相較於一般可應用於DVD光碟片染 料之化合物價格較為低廉。新型吲哚苯乙烯鹽化合物所1 有的R1側基可提升其結構的光敏感度,以及極佳的對於光 和熱之化學穩定性。而且新型吲哚苯乙烯鹽化合物對於有
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極佳之溶解度利 乙烯鹽化 較於一般 為低廉, 錄式光碟 定的優點 佳實施例 熟習相關 作些許之 說明書所 合物使 乙烯鹽化合物染 應用於 可以達 片所使 機溶劑 因此, 碟片, 光碟片 染料之 並且可 光,並 雖 以限定 精神和 專利保 為準。 更具有 將新型 以新型 的記錄 化合物 配合高 且具有 然本發 本發明 範圍内 言隻範圍 吲哚苯 吲哚笨 層。相 價格較 密度可 品質穩 明之較 ,任何 ,當可 須視本 揭露如 技藝者 更動與 附之申 片的旋轉塗佈製程。 用於高密度可錄式光 料形成高密度可錄式 高密度資訊儲存媒體 到降低成本的-功效。 用之較短波長的雷射 上所述,然其並非用 ,在不脫離本發明之 潤飾,因此本發明之 請專利範圍所界定者 589349 _案號91108158_年月曰 修正_ 圖式簡單說明 第1圖為使用新型吲哚苯乙烯鹽化合物染料之高密度 可錄式光碟片的應用實施例示意圖;及 第2圖為本發明應用實施例的高密度可錄式光碟片反 射率對波長之光譜圖。 【圖式符號說明】
10 第一基板 20 記錄層 30 反射層 40 樹脂保護層 50 貼合層 60 第二基板
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Claims (1)

  1. 589349 案號 91108158 六、申請專利範圍 其中當R1為含1至8個碳((^δ)之烷基時,X-為四氰基 -對奎諾二曱烷(TCNQ-, 土 teteacyano-p-quinodimethane)·、四氰乙烯(TCNE' , tetracyanoethylene)所組成的族群其中之一。 2 ·如申凊專利範圍第1項所述之新型卩引卩朵'苯.乙烯鹽化合 物,其中R6係選自含1至8個碳(Ci—8)之烷基(CO# )與 氟烧基(CJ4, CF3)所組成的族群其中之一。 3·如申請專利範圍第丨項所述之新型吲哚苯乙烯鹽化合 物,其中R7係為含1至8個碳之烷基(c〇2R8 )。 4_如申請專利範圍第1項所述之新型吲哚苯乙烯鹽化合 =,其中R4和R5係為含丄至8個碳(Ch)之烷基(c〇2R8 ) 日守’ R8係選自含1至8個碳(Cu )之烷基(⑶2γ)與氟烷 基(G F4、CF3 ) 所組成的族群其中之一。 5 ·如申請專利範圍第1項所述之新型吲哚笨乙烯鹽化合 物’其中R4和R5係為醯胺基(―CONRgR10 )時,R9與R1Q可為 氳原子和含1至6個碳(Ci e)之烷基所組成的族群其中之 6 ·如申凊專利範圍第1項所述之新型吲哚苯乙烯鹽化合 物,其中R4和R5係為磺酸酯基(―S〇3Rii)時,R11可為氫原 子和合1至6個碳()之烧基所組成的族君羊其中之一。 7· —種高密度可錄式光碟片,其包含有: 一第一基板,係為透明基板; / 一記錄層,該記錄層係由一新型吲哚苯乙烯鹽化合 物形成於該第一基板表面,其中該新型吲哚苯乙烯鹽化
    589349 案號 91108158 六、申請專利範圍 合物 月 曰 修正 具有如下之化學結構式:
    ① 該化學結構式之紐成為: R1係選自含1至8個碳(Ci_8)之烷基 酯基團(CH2C6H4C02R7)、含個 2 )本王衣 ^^/rux〇nn7 k )之直鏈烧石备酸 酉日基(CH2)nS03R與直鏈烷酯基(CH ) /、 其中之一; n2^LU2R所組成的族群 R2和R3係分別為相同或不同之基目,係選自氫原 子、含1至8個碳(Ch)之烷基、含!至8個碳(c ^浐 基、/含含1"至8個礙(Cl_8)之院醋基(―c〇2R8 )與8於和^相 連形成含氮雜環所組成的族群其中之一; R4和R5係選自氫原子、含i至8個碳(Ch )之烷基、二 氟曱基、烧氧基、魏基、硝基、磺酸基、績酸酯美 (SOgR9)醯胺基、含1至8個碳之烷酯基與鹵素原 的族群其中之. 、卞所組成 Y—係選自四氰基-對奎諾二曱烷(TCNQ-, teteacyan〇-p-quinodimethane)、四氰乙烯(TCNE—, tetracyanoethylene)、過氯酸根(C104-)、六氣銻㉒蹄 (SbF6-)、六氟磷酸鹽(PF6~)、四氟硼酸鹽(bf4)和自Ί 589349 -案號91108158 生 η 日 修正 六、申請專利範圍 離子其中之一;及 其中當R1為含1至8個碳(u之烷基(c〇2R8 )時,X- 為四氰基-對奎諾二曱烷(TCNQ-, teteacyano-p-quinodimethane)、四氰乙烯(TCNE一, tetracyanoethylene)所組成的族群其中之一; 一反射層,係配置於該記錄層上; 一第二基板,係為透明基板;及 一貼合層,係用以貼合該反射層與該第二基板。 8 ·如申請專利範圍第7項所述之高密度可錄式光碟片,其 中R6係選自含1至8個碳(Ch)之烷基(C02R8 )與氟烷基 (C2 F4、CF3)所組成的族群其中之一。 9 ·如申請專利範圍第7項所述之高密度可錄式光碟片,其 中R7係為含1至8個碳(Ch)之烷基(c〇2R8 )。 10·如申請專利範圍第7項所述之高密度可錄式光碟片,其 中R4和R5係為含1至8個碳(Ch)之烷基(CO# )時,R8 係選自含1至8個碳(Cl_8)之烷基(C02R8 )與氤烷基 (C2 F4、CF3)所組成的族群其中之一。 11.如申請專利範圍第7項所述之高密度可錄式光碟片,其 中R4和R5係為醯胺基(_C0NR9R1G)時,R9與R1G可為氮原子 和含1至6個碳(ci-6 )之烷基所組成的族群其中之一。 1 2 ·如申請專利範圍第7項所述之高密度可錄式光碟片,其 中R4和R5係為磺酸酯基(-SOgR11)時,R11可為氫原子和含 1至6個碳(Ch )之烷基所組成的族群其中之—。 1 3 ·如申請專利範圍第7項所述之高密度可錄式光碟片,該
    第28頁 589349 1號 911081Μ 曰 修正 六、申請專利範圍 弟基板與該第二基板係為一具有溝軌(land)及溝样 (groove)之透明基板,其軌距(track pitch)係為〇曰微米至0 · 8微米(mm ),溝深(gr ο 〇 ve dep t h )係為7 〇太、, 至200奈米(nm)。 示来 14·如申請專科範圍第7項所述之高密度可錄式光碟片 中該第一基板與該第二基板之材質可係為聚酯類 石炭酸酉1類(Polycarbonat,PC)與聚烯類其中之_ 1 5·如申請專利範圍第7項所述之高密度可錄式光碟片,」 中該記錄層形成方式,係將該新型吲哚苯乙稀鹽化合 物透過旋轉塗佈、真空蒸鍍、喷佈、滾壓塗佈與含浸 其中之一方法以形成該記錄層。 1 6 ·如申請專利範圍第7項所述之高密度可錄式光碟片,其 中該記錄層之膜厚係為7〇奈米至2 50奈米(nm)。 1 7 ·如申睛專利範圍第7項所述之高密度可錄式光碟片,其 中該記錄層之形成方式,係將該新型吲哚笨乙烯鹽化 合物溶於一有機溶劑再以旋轉塗佈方法塗佈於該第一 基板表面以形成該記錄層。 1 8 ·如申晴專利範圍第1 7項所述之高密度可錄式光碟片, 其中該有機溶劑係為含1至6個碳(匕_6)之醇類 (alcohol )、含1 至6 個碳(Ci 6)之酮類(ket〇ne )、 含1至6個碳(ci-6)之醚類(ether) 、i素化合物 烧類及醯胺(amide)其中之一。 1 9.如申凊專利範圍第1 8項所述之高密度可錄式光碟片 其 其 環
    589349 案號 91108158 年 月曰、 修正 六、申請專利範圍 其中該含1至6個碳(Ch)之醇類係為曱醇(methanol )、乙醇(ethanol )、異丙醇(isopropanol )、二 丙嗣醇(diacetonalchol ;DAA) 、2,2,3,3 -四氟丙醇 (2, 2,3,3-tetrafluoropropanol )、三氯乙醇 (tr i ch' 1 oroe thafnο 1 ) 、2- 氯乙酉享(2- ch 1 oroe tirano 1 )、八氟戍醇(octafluoropentanol)、六氟丁醇 (hexafluorobutanol )其中之一。
    2 〇.如申請專利範圍第1 8項所述之高密度可錄式光碟片, 其中該1至6個碳(Ci_6)之酮類係為丙酮(acetone )、 甲基異丁酮(methyl isobutyl ketone, MIBK)、曱 基乙基酮(methyl ethyl ketone,MEK)與3 -經基-3-曱基-2- 丁酮(3-hydroxy-3-methyl-2-butanone )其 中之一。 21 ·如申請專利範圍第1 8項所述之高密度可錄式光碟片, 其中該鹵素化-合物係為氯仿(chloroform )、二氯甲 烧(dichloromethane)、及1—氯丁烧 (1 - c h 1 〇 r 〇 b u t a n e )其中之一。 2 2 ·如申請專利範圍第1 8項所述之高密度可錄式光碟片,
    其中該環烷類係為曱基環己烷(Methyl cyclohexane, MCH) 2 3 ·如申請專利範圍第1 8項所述之南洽、度可錄式光碟片’ 其中該醯胺係為二曱基甲醯胺(dimethylformamide, DMF )、及二甲基乙 ϋ 胺(dimethy lacetamide, DMA ) 其中之一。
    第30頁 589349 _案號91108158_年月日__ 六、申請專利範圍 2 4.如申請專利範圍第7項所述之高密度可錄式光碟片,其 中該反射層係為金、銀、銘、石夕、銅、銀鈦合金、銀 鉻合金、銀銅合金及其任意組合之合金其中之一。 25. 如申請專利範圍第7項所述之高密度可錄式光碟片,其 中以該貼合層之貼合方式係為翁轉塗佈法、網印、熱 融膠法、雙面膠帶貼合法其中之一。 26. 如申請專利範圍第7項所述之高密度可錄式光碟片.,其 中該反射層的膜厚係為50奈米至200奈米(nm)。 27. 如申請專利範圍第7項所述之高密度可錄式光碟片,其 中更包含重疊複數個記錄層以及複數個反射層以形成 一多層高密度可錄式光碟片。
    第31頁
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JP2002277031A JP3961385B2 (ja) 2002-04-19 2002-09-24 インドールスチリル化合物およびこれを用いた高密度記録媒体
DE10249654A DE10249654B4 (de) 2002-04-19 2002-10-24 Neue Indolstyryl-Verbindungen und ihre Verwendungen in Aufzeichnungsmedien mit hoher Dichte
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JP5100635B2 (ja) * 2006-03-31 2012-12-19 株式会社Adeka インドリウム化合物及び光学記録材料
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