CN101073115A - 单取代的方形酸金属络合物染料以及其在用于光学数据记录的光学层中的应用 - Google Patents

单取代的方形酸金属络合物染料以及其在用于光学数据记录的光学层中的应用 Download PDF

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CN101073115A
CN101073115A CNA200580039678XA CN200580039678A CN101073115A CN 101073115 A CN101073115 A CN 101073115A CN A200580039678X A CNA200580039678X A CN A200580039678XA CN 200580039678 A CN200580039678 A CN 200580039678A CN 101073115 A CN101073115 A CN 101073115A
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alkyl
aryl
replace
hydrogen
independently
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A·韦斯
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Clariant Finance BVI Ltd
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Clariant Finance BVI Ltd
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Abstract

本发明涉及新的单取代方形酸金属络合物染料以及其在用于光学数据记录的光学层中的应用，优选用于使用波长高达450纳米的激光的光学数据记录。本发明此外涉及能够使用蓝色激光辐射记录和再生信息的一次写入多次读取(WORM)型光记录介质，其在光学层中使用单取代方形酸金属络合物染料。

Description

单取代的方形酸金属络合物染料以及 其在用于光学数据记录的光学层中的应用
本发明涉及新的单取代方形酸金属络合物染料，以及其在用于光学数据记录的光学层中的应用，优选使用波长高达450纳米的激光的光学数据记录。
本发明此外涉及能够使用蓝色激光辐射记录和再生信息的一次写入多次读取(WORM)型光学记录介质，其在光学层中使用单取代的方形酸金属络合物染料。
最近，有机染料在二极管-激光光学存储器领域非常引人注目。作为记录层，商用可记录光盘(CD-R)和可记录数字通用磁盘(DVD-R)可含有基于酞菁、半花青、花青和金属化偶氮结构的多种染料。这些染料在其各自领域适于激光波长标准。对于染料介质的其它一般要求为强吸收、高反射、高记录敏感性、低导热性，以及光和热稳定性、储存耐久性或无毒性。
对于工业应用，这些染料必须适于旋涂工艺以制备薄膜，亦即其必须充分溶于旋涂工艺中通常使用的有机溶剂。
通过测定物理变形所引起的反射系数的变化、通过改变光学特性以及通过记录前后记录层的相和磁性质，WORM(一次写入多次读取)型和可擦写型光学记录介质再生信息。
可记录光盘(CD-R)普遍已知用作WORM型光学记录介质。最近，具有高达4.7千兆字节的升高信息存储性能的数字通用磁盘(DVD)已经商业化。
DVD-R技术采用波长为630-670纳米的红二极管激光作为光源。因此凹点大小和轨道间距可以减小，与CD-R相比信息存储能力可以提高6-8倍。
Blu-ray磁盘(Blu-ray磁盘为Hitachi Ltd.、LG Electronics Inc.、Matsushita Electric Industrial Co.Ltd.、Pioneer Corporation、RoyalPhilips Electronics、Samsung Electronics Co.Ltd.、Sharp Corporation、Sony Corporation、Thomson Multimedia研发的标准)将要成为光学记录工艺的下一个里程碑。对于12厘米直径磁盘，其新规范将数据存储增加到每个记录层高达27千兆字节。通过使用波长为405纳米的蓝色二极管激光(GaN或SHG激光二极管)，凹点大小和轨道间距可以进一步减小，将存储容量再次增加一个数量级。
光学数据记录介质的构造为本领域已知。光学数据记录介质通常包括衬底和记录层、光学层。通常有机聚合材料的磁盘或光学转换器(waver)用作衬底。优选的衬底为聚碳酸酯(PC)或聚甲基丙烯酸甲酯(PMMA)。衬底必须提供平坦、均匀的高光学性能的表面。光学层以高光学性能和确定厚度的均匀薄膜沉积在其上。最后，例如铝、金或铜的反射层沉积在光学层上。
高级的光学数据记录层可包括其它层，例如保护层、粘合层或其它光学层。
为了提供光学层薄而均匀的薄膜，材料通常通过旋涂、真空蒸发、喷涂、辊涂或浸涂沉积。工业中的优选方法为旋涂以形成约70纳米至250纳米厚的光学层。对于旋涂工艺中的应用，光学层材料必须高度溶于有机溶剂。
EP 1334998 A1(Kyowa Hakko Kygyo)、EP 1449890 A1(Ricoh，Kyowa Hakko Kygyo)、EP 1335357 A1(Kyowa Hakko Kygyo)和EP1267338 A2(Kyowa Hakko Kygyo)公开了以下通式表示的方形酸金属螯合物，以及具有包括这种方形酸金属螯合物的记录层的记录介质。
WO 2003085005 A1(Kyowa yuka KK)公开了含有下式方形酸化合物金属络合物的光可聚合组合物：
Figure A20058003967800091
Matsui等人(Dyes and Pigments  58，2003，219-226)公开了作为TiO2太阳能电池敏化剂的3-芳基-4-羟基环丁-3-烯-1，2-二酮，即一种单取代方形酸化合物。
现已惊奇地发现，如下所示的单取代方形酸衍生物的金属络合物在光学层中可用作光记录介质的染料化合物。
本发明因此涉及如下所示的新的单取代方形酸衍生物的金属络合物、其在含有单取代方形酸化合物的金属络合物的光学层中的应用，并且涉及所述光学层作为光学数据记录介质的应用。
更具体而言，本发明涉及能够使用优选405纳米蓝色激光辐射记录和再生信息的一次写入多次读取(WORM)型光学数据记录介质，其在光学层中使用单取代方形酸染料。
本发明涉及式(I)的染料化合物或其互变异构形式的一种。
Figure A20058003967800092
其中
X表示去质子化的羟基(-OH)、硫醇(-SH)或胺(NHR1)，其中R1表示氢、C1-12烷基(未取代或者被以下基团取代：羟基(-OH)、C6-12芳基、卤素、-NR9R10′，其中R9和R10独立地为氢、C1-12烷基或C6-12芳基)、苄基或C6-12芳基；
Y表示氧、硫或亚胺-氮N-R2，其中R2表示氢、C1-12烷基(未取代或者被以下基团取代：羟基(-OH)、C6-12芳基、卤素、-NR′R″，其中R′和R″独立地为氢、C1-12烷基或C6-12芳基)、苄基或C6-12芳基；
z表示-2到+2的电荷；
An-表示以下阴离子配对物(counter-part)，选自无机阴离子，例如碘、氟、溴、氯、高氯酸盐、六氟锑酸盐、六氟磷酸盐、四氟硼酸盐、四苯基硼酸盐，或有机阴离子，例如二氰基酰胺(N(CN)2)或者三氟甲磺酰亚胺(N(SO2CF3)2)；或An-还可为阴离子偶氮金属络合物，
M表示金属离子；
A为五元或六元芳香或杂芳香环，其可被进一步取代或退火，
n表示1-4的整数。
在一个优选方面，本发明涉及式(I)的染料化合物，
其中
X表示去质子化的羟基(-OH)或硫醇(-SH)；
Y表示氧或硫；
z表示0到+1的电荷；
An-表示以下阴离子配对物，选自无机阴离子，例如氯、高氯酸盐、六氟锑酸盐、六氟磷酸盐、四氟硼酸盐、四苯基硼酸盐，或有机阴离子，例如二氰基酰胺(N(CN)2)或者三氟甲磺酰亚胺(N(SO2CF3)2)；或
An-还可为阴离子偶氮金属络合物，
M表示金属离子，选自Ca，Sr，Ba，Al，Ga，In，Sc，Y，Ti，Zr，V，Nb，Ta，Cr，Mo，W，Mn，Fe，Ru，Os，Co，Rh，Ir，Ni，Pd，Pt，Cu，Ag，Au，Zn，Cd，Hg，La，Ce，Pr，Nd，Pm，Sm，Eu，Gd，Tb，Dy，Ho，Er，Tm，Yb，Lu；
n表示1-4的整数
选择A以形成以下基团的一种或其互变异构形式的一种：
Figure A20058003967800111
其中
R3和R4彼此独立地表示氢；C1-8烷基，其中所述烷基可未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；CX3，其中X可为氯、氟、溴；C6-12芳基，其可未取代或者被C1-8烷基、羟基(-OH)、硝基(-NO2)、氰基(-CN)、卤素、C6-12芳基、-NR9R10或者C1-8烷氧基(-OR)取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；
R5-R8各自独立地表示氢、氰基(-CN)、卤素、硝基(-NO2)、羟基、直链或支链C1-8烷氧基(-OR)，其中烷基(R)未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；氨基(-NR9R10)，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基，或者R9和R10可形成可含有其它杂原子的五元或六元环；直链或支链C1-8烷基，其中烷基可未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；CX3，其中X可为氯、氟、溴；直链或支链C1-8烷硫基，其中烷基未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；C6-12芳基，其未取代或者被C1-8烷基、羟基(-OH)、硝基(-NO2)、氰基(-CN)、卤素、C6-12芳基、-NR9R10或者C1-8烷氧基(-OR)取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基。
在更加优选的方面，本发明涉及式(I)的染料化合物，其中
X表示去质子化的羟基(-OH)；
Y表示氧；
z表示0到+1的电荷；
An-表示氯；
M表示金属离子，选自Al，Y，Zr，Cr，Fe，Co，Ni，Cu，Zn，Yb；
n表示2-3的整数；
选择A以形成以下基团的一种或其互变异构形式的一种：
Figure A20058003967800121
其中
R3和R4彼此独立地表示氢；C1-8烷基，其中所述烷基可未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；C6-12芳基，其可未取代或者被C1-8烷基、羟基(-OH)、硝基(-NO2)、氰基(-CN)、卤素、C6-12芳基、-NR9R10或者C1-C8烷氧基(-OR)取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；
R5-R8各自独立地表示氢、氰基(-CN)、卤素、硝基(-NO2)、羟基、直链或支链C1-8烷氧基(-OR)，其中烷基(R)未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；氨基(-NR9R10)，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基，或者R9和R10可形成可含有其它杂原子的五元或六元环；直链或支链C1-8烷基，其中烷基可未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；CX3，其中X可为氨、氟、溴；直链或支链C1-8烷硫基，其中烷基未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；C6-C12芳基，其未取代或者被C1-8烷基、羟基(-OH)、硝基(-NO2)、氰基(-CN)、卤素、C6-12芳基、-NR9R10或者C1-C8烷氧基(-OR)取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基。
在最优选实施方案，本发明涉及式(II)染料化合物，
其中
z表示0到+1的电荷；
An-表示氯；
M表示金属离子，选自Al，Zr，Cr，Co，Ni，Cu，Zn；
n表示2-3的整数；
R3表示苯基或对甲苯基，
R4表示甲基或苄基，
R5表示甲基或苯基。
本发明此外涉及含有如上所示式(I)染料化合物的光学层，并且涉及所述光学层用于光学数据记录介质的应用。根据本发明的光学层还可包括两个或多个，优选两个如上所示式(I)染料化合物的混合物。
当用于根据本发明光学数据记录介质的光学层中时，式(I)单取代方形酸金属络合物染料提供特别优选的性质。
优选的衬底为聚碳酸酯(PC)或聚甲基丙烯酸甲酯(PMMA)。
有机溶剂选自C1-8醇、卤素取代的C1-8醇、C1-8酮、C1-8醚、卤素取代的C1-4烷烃或酰胺。
优选的C1-8醇或卤素取代的C1-8醇例如为甲醇、乙醇、异丙醇、二丙酮醇(DAA)、2，2，3，3-四氟丙醇、三氯乙醇、2-氯乙醇、八氟戊醇或六氟丁醇。
优选的C1-8酮例如为丙酮、甲基异丁酮、甲乙酮或3-羟基-3-甲基-2-丁酮。
优选的卤素取代的C1-4烷烃为例如氯仿、二氯甲烷或1-氯丁烷。
优选的酰胺为例如二甲基甲酰胺或二甲基乙酰胺。
所得光学层(染料层)优选具有70-250纳米的厚度。
在一个优选方面，本发明提供在350-450纳米，优选约405纳米激光波长范围适于高密度记录材料例如WORM磁盘形式的光学层。
式(I)染料化合物具有所需光学特性(例如高吸收性、高记录敏感性)、有机溶剂中极好的溶解性、极好的光稳定性和250-300℃的分解温度。
本发明方形酸金属络合物染料的制备
通过使杂环化合物(A)与方形酸衍生物(B)在极性溶剂中以1∶1的比例反应得到式(I)的单取代方形酸金属络合物染料。在加入或不加入辅助碱的条件下，所得单方形酸染料(C)与可在反应过程中氧化的金属盐在极性溶剂中反应。
阴离子交换可在化合物(I)上在惰性溶剂中在回流条件下与适于交换的相应的反离子进行。
Figure A20058003967800141
制备式(I)染料的方法可以描述为以下步骤：
(a)(A)和(B)反应以形成半方形酸(C)。
(b)在加入或不加入辅助碱的条件下，半方形酸(C)与金属盐的反应。
(c)如果化合物(I)带有正电荷，可使用惰性溶剂和合适的反离子在化合物(I)上进行阴离子交换。
(A)和(B)缩合步骤(步骤(a))的优选溶剂选自下组：酮(丙酮、甲乙酮)、醇(甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇)、卤代溶剂(二氯甲烷、三氯甲烷)或芳香烃溶剂(苯、甲苯、邻、间、对二甲苯、邻二氯苯)，或其混合物。
步骤(b)的优选溶剂选自下组：酮(丙酮、甲乙酮)、醇(甲醇、乙醇、1-丙醇、2-丙醇)或卤代溶剂(二氯甲烷、三氯甲烷)，或其混合物。
步骤(c)的优选溶剂选自下组：甲乙酮、二氯甲烷、乙腈或2-丙醇(propanole)，或其混合物。
光学层的制备
根据本发明的光学层包括式(I)染料或式(I)染料混合物。
形成根据本发明光学层的方法包括以下步骤：
(a)提供衬底，
(b)将式(I)染料化合物或式(I)染料化合物混合物溶于有机溶剂以形成溶液，
(c)将溶液(b)涂布在衬底(a)上；
(d)蒸发溶剂以形成染料层。
高密度光学记录介质的制备
制备包括本发明光学层的光学记录介质的方法包括以下另外的步骤：
(e)在染料层上溅射金属层，
(f)施加基于聚合物的第二层以完成磁盘。
根据本发明的高密度数据存储介质因此优选可记录光盘，其包括：第一衬底，其为具有沟槽的透明衬底；记录层(光学层)，其使用式(I)染料形成在第一衬底表面；形成在记录层上的反射层；第二衬底，其为使用连接层连接到反射层的具有沟槽的透明衬底。
(a)衬底
衬底，作为施加于其上的层的载体，有利地为半透明(T＞10％)或优选透明(T＞90％)。载体可具有0.01-10毫米，优选0.1-5毫米的厚度。
合适的衬底例如为玻璃、矿物质、陶瓷、热固化或热塑性塑料。优选的载体为玻璃和均或共聚塑料。合适的塑料例如为热塑性聚碳酸酯、聚酰胺、聚酯、聚丙烯酸酯和聚甲基丙烯酸酯、聚氨酯、聚烯烃、聚氯乙烯、聚偏二氟乙烯、聚酰亚胺、热固化聚酯和环氧树脂。
最优选的衬底为聚碳酸酯(PC)和聚甲基丙烯酸甲酯(PMMA)。
衬底可为纯体形式或可含有常规添加剂，例如紫外线吸收剂或染料，如JP 04/167239中建议了记录层中的光稳定剂。在后一种情形，染料还可有利地加入到衬底中，以具有与记录层染料有关的至少10纳米优选至少20纳米的最大吸收蓝移移动。衬底有利地在350-500纳米的至少一部分透明，以使得其能够透过写入或读出波长的入射光的至少90％。
(b)有机溶剂
有机溶剂选自C1-8醇、卤素取代的C1-8醇、C1-8酮、C1-8醚、卤素取代的C1-4烷烃或酰胺。
优选的C1-8醇或卤素取代的C1-8醇例如为甲醇、乙醇、异丙醇、二丙酮醇(DAA)、2，2，3，3-四氟丙醇、三氯乙醇、2-氯乙醇、八氟戊醇或六氟丁醇。
优选的C1-8酮例如为丙酮、甲基异丁酮、甲乙酮或3-羟基-3-甲基-2-丁酮。
优选的卤素取代的C1-4烷烃为例如氯仿、二氯甲烷或1-氯丁烷。
优选的酰胺为例如二甲基甲酰胺或二甲基乙酰胺。
(c)记录层
记录层(光学层)优选设置在透明衬底和反射层之间。记录层的厚度为10-1000纳米，优选30-300纳米，尤其约80纳米，例如60-120纳米。
式(I)染料的使用产生具有高折射率的均匀、无定型和低分散的记录层。即便是在固相，吸收边缘也惊人陡峭。其它优点为在日光和低功率密度激光辐射下的高光稳定性，同时对高功率密度激光辐射的高敏感性、均匀的脚本宽度、高对比度、以及良好的热稳定性和储存稳定性。
不含有式(I)单一化合物，记录层中还可含有根据本发明的这些化合物的混合物。通过使用混合物，例如异构体或同系物以及不同结构的混合物，通常可以增加溶解度和/或提高无定型含量。
如JP04/025493所述，为了进一步增加稳定性，如果需要的话，其还可能加入常规量的已知稳定剂，例如作为稳定剂的二硫醇镍(nickel dithiolate)。
记录层优选以足以显著影响折射率的量含有式(I)化合物或这些化合物的混合物，例如至少30重量％，更优选至少60重量％，最优选至少80重量％。
其它常用的组分例如为其它发色团(例如WO-01/75873中公开的那些，或在300-1000纳米具有最大吸收的那些)、稳定剂、1O2-、三重态或荧光淬灭剂、熔点降低剂、分解促进剂或者光学记录介质中已经公开的任意其它添加剂。如果需要的话，优选加入稳定剂或荧光淬灭剂。
当记录层另外包括其它发色团时，其基本上可为在记录期间可通过激光辐射分解或改性的任意染料，或者其可对激光辐射惰性。当其它发色团通过激光辐射分解或改性时，其可通过吸收激光辐射直接进行，或者可通过例如加热分解本发明式(I)化合物间接进行。
其它发色团或颜色稳定剂可自然影响记录层的光学性质。因此优选使用其它发色团或颜色稳定剂，其光学性质尽可能与式(I)化合物一致，或者尽可能不同，或者其它发色团的量保持很小。
当使用与式(I)化合物光学性质尽可能一致的其它发色团时，优选位于最长波长吸收侧面。其它发色团转化点式(I)化合物的波长间隔优选最大20纳米，尤其优选最大10纳米。在那种情况下，其它发色团和式(I)化合物将表现出与激光辐射类似的情形，由此可能使用已知记录剂作为其它发色团，其作用通过式(I)化合物协同增强。
当其它发色团或颜色稳定剂具有与使用的式(I)化合物尽可能不同的光学性质时，它们有利地具有最大吸收，其为与式(I)染料有关的蓝移或红移的移动。在那种情况下，最大吸收相差优选至少50纳米，尤其优选至少100纳米。
其实例为向式(I)染料蓝移的紫外线吸收剂或向式(I)染料红移的颜色稳定剂，并且例如在NIR或IR范围内具有最大吸收。
为了颜色编码识别、颜色掩蔽(“金刚石染料”)或增强记录层样式美观的目的，还可加入其它染料。在所有这些情况下，其它发色团或颜色稳定剂将优选表现出对光和激光辐射尽可能惰性的性能。当加入其它染料以改性式(I)化合物的光学性质时，其加入量将取决于要得到的光学性质。本领域技术人员在改变染料与式(I)化合物比例以得到其所需结果时没有任何困难。
当发色团或颜色稳定剂用于其它目的时，其量优选较少以使得其对记录层在350-500纳米范围内总吸收的贡献最大为20％，优选最大10％。在这种情况下，基于记录层的重量，其它染料或稳定剂的加入量有利地最大为50％，优选最大10％。
然而最优选不加入其它发色团，除非其为颜色稳定剂。
稳定剂、1O2-、三重态或发光淬灭剂例如为含N-或S-烯醇盐、酚盐、二酚盐、硫醇盐或二硫醇盐的金属络合物，或偶氮、偶氮甲碱或甲腊染料的金属络合物，例如双(4-二甲氨基二硫偶苯酰)镍[CAS登记号：38465-55-3]。受阻酚及其衍生物例如邻羟基苯三唑或三嗪或其它紫外线吸收剂，例如受阻胺(TEMPO或HALS，以及硝基氧或NOR-HALS)，以及阳离子diimmonium、ParaquatTM或Orthoquat盐，例如Kayasorb IRG 022、Kayasorb IRG 040、还任选基团离子，例如N，N，N′，N′-四(4-二丁氨基苯基)对苯胺-六氟磷酸铵、六氟锑酸铵或高氯酸铵。后者得自Organica(Wolfen/DE)；Kayasorb商标得自Nippon Kayaku Co.Ltd。
本领域熟练技术人员将从其它光学信息介质获悉，或者将容易确定最适于其目的的添加剂浓度。基于式(I)记录介质，合适的添加剂浓度例如为0.001-1000重量％，优选1-50重量％。
(e)反射层
适于反射层的反射材料尤其包括金属，其对用于记录和读出的激光辐射提供良好的反射，例如元素周期表中主族III、IV和V以及副族中的金属。尤其合适的是AI，In，Sn，Pb，Sb，Bi，Cu，Ag，Au，Zn，Cd，Hg，Sc，Y，La，Ti，Zr，Hf，V，Nb，Ta，Cr，Mo，W，Fe，Co，Ni，Ru，Rh，Pd，Os，Ir，Pt，Ce，Pr，Nd，Pm，Sm，Eu，Gd，Tb，Dy，Ho，Er，Tm，Yb，Lu以及其合金。由于其高反射率和易于生产，特别优选铝、银、铜、金或其合金的反射层。
(f)覆盖层/保护层
适于覆盖层/保护层的材料包括塑料，其适于直接或使用粘合层辅助以薄层的形式施加到载体或最上层。有利地选择具有良好表面性质的机械和热稳定塑料，其可进一步改性。
塑料可为热固性塑料和热塑性塑料。优选辐射硬化(例如使用紫外辐射)的保护层，其制备时特别简单和经济。各种辐射硬化的材料是已知的。辐射硬化单体和寡聚物的例子为二醇、三醇和四醇的丙烯酸酯和甲基丙烯酸酯、芳香族四羧酸的聚酰亚胺，和在氨基的至少两个邻位具有C1-C4烷基的芳族二胺，以及具有二烷基马来酰亚胺基例如二甲基马来酰亚胺基的寡聚物。
根据本发明的记录介质还可具有附加层，例如干涉层。还可能构造具有多个(例如两个)记录层的记录介质。这些材料的结构和使用为本领域熟练技术人员所公知。如果存在的话，干涉层优选排列在记录层和发射层之间，和/或在记录层和衬底之间，并且由绝缘材料组成，例如EP 0353393中所述的TiO2、Si3N4、ZnS或硅酮树脂。
根据本发明的记录介质可通过本领域已知方法制备。
涂层方法
合适的涂层方法例如为浸渍、浇注(pouring)、刷涂、刀涂(blade-application)和旋涂，以及在高真空进行的气相沉积方法。当使用浇注时，通常使用在有机溶剂中的溶液。当使用溶剂时，应当注意使得使用的载体对这些溶剂不敏感。合适的涂层方法和溶剂例如公开在EP-A-401791中。
记录层优选使用染料溶液通过旋涂施加，已经证明令人满意的溶剂优选醇，例如2-甲氧基乙醇、正丙醇、异丙醇、异丁醇、正丁醇、戊醇或3-甲基-1-丁醇，或者优选氟化醇，例如2，2，2-三氟乙醇或2，2，3，3-四氟-1-丙醇、八氟戊醇及其混合物。应理解还可使用其它溶剂或溶剂的混合物，例如EP-A-511 598和EP-A-833 316中所述的溶剂混合物。还可使用醚(二丁醚)、酮(2，6-二甲基-4-庚酮、5-甲基-2-己酮)或饱和或不饱和烃(甲苯、二甲苯)，例如混合物(例如二丁醚/2，6-二甲基-4-庚酮)形式或混合组分。
旋涂领域普通技术人员通常将试验其熟悉的所有溶剂以及其二元或三元混合物，以找到产生较高品质同时有效益的含所选固体组分的记录层的溶剂或溶剂混合物。工艺过程的已知方法还可用于这些优化过程，以使得试验数量保持在最小程度。
本发明还涉及制备光学记录介质的方法，其中式(I)化合物在有机溶剂中的溶液施加到具有凹点的衬底上。施加优选通过旋涂进行。
金属反射层的施加优选通过溅射、真空气相沉积或化学气相沉积(CVD)进行。由于高度粘合到载体上，对于金属反射层的施加尤其优选溅射工艺。这些工艺已知并且公开在专业文献中(例如J.L.Vossen和W.Kern，“Thin Film Processes”，Academic Press，1978)。
读取方法
根据本发明记录介质的结构主要通过读取方法控制；已知的功能原理包括测量投射或优选反射中的变化，然而除了投射或反射外还已知测量例如荧光。
当记录材料为了反射变化构造时，可使用以下构造：透明载体/记录层(任选多层)/反射层和，如果合适的话，保护层(不一定透明)；或载体(不一定透明)/反射层/记录层和，如果合适的话，透明保护层。在第一种情况下，光从载体侧发出，然而在后一种情形，辐射从记录层侧发出，或者在合适的情况下从保护层侧发出。在全部情况下，光检测器位于光源的同一侧。根据本发明使用的第一种所述记录材料的构造通常是优选的。
当记录材料为光透射改变构造时，可考虑以下不同结构：透明载体/记录层(任选多层)和，如果合适的话，透明保护层。用于记录和读出的光可由载体侧入射或者由记录层侧入射，或者，如果合适的话，从保护层侧入射，在这种情况下，光检测器总是位于光源的同一侧。
合适的激光为波长为350-500纳米的那些，例如波长为405-414纳米的市场上可买到的激光，例如半导体激光器。通过将激光调节成与标记长度一致并且将其辐射集中到记录层上，记录例如点对点进行。专业文献已知当前正在研制适于应用的其它方法。
本发明方法容许信息以较大可靠性和稳定性存储，区别在于非常好的机械稳定性和热稳定性以及高度光稳定性和明显的凹点界面区。特别优点包括高对比度、低图像跳动和意外高的信噪比，由此实现极好的读取。
信息读出根据本领域已知的方法通过记录使用激光辐射时吸收或反射的改变进行，例如公开在“CD-Player and R-DAT Recorder”(ClausBiaesch-Wiepke，Vogel Buchverlag，W[upsilon]rzburg 1992)。
本发明光学记录介质优选为WORM型可记录光盘。例如，还可用作可播放HD-DVD(高密度数字通用磁盘)或Blu-ray磁盘，作为计算机存储介质或作为识别或安全卡片，或用于制备衍射光学元件，例如全息图。
本发明由此涉及一种信息的光学记录、存储或回放方法，其中使用根据本发明的记录介质。所述记录和回放有利地在350-500纳米的波长范围内进行。
现已发现，与现有技术中已知的染料相比，本发明式(I)的新染料提高了对光和热的光敏性和稳定性。本发明(I)的新染料具有250-350℃的分解温度。另外，这些化合物显示出在有机溶剂中极好的溶解性，其对于制造光学层的旋涂法非常理想。
因此，在高密度可记录光盘中使用这些新化合物非常有利。
实施例
以下实施例用于说明本发明而不会限制本发明范围。在以下实施例中除非另有说明，“份”总为重量份。
实施例1
100份1-苄基-5-甲基-2-对甲苯基-1，2-二氢吡唑-3-酮和41份3，4-二羟基-3-环丁烯-1，2-二酮在810份1-丁醇和390份甲苯的混合物中回流7小时。在回流期间，生成的水使用脱水器分离。冷却后将沉淀的产物过滤并用1-丁醇洗涤，得到70份3-(1-苄基-5-甲基-3-氧代-3-对甲苯基-2，3-二氢-1H-吡唑-4-基)-4-羟基-环丁-3-烯-1，2-二酮。1H-NMR(500MHz，D6-DMSO)：δ＝2.35(s，3H)，2.78(s，3H)，5.14(s，2H)，6.92(m，2H)，7.17(m，2H)，7.30(m，5H).
UV-V是(MeOH)λmax：343nm；ε(λmax)：75 Lg-1cm-1.
Figure A20058003967800211
实施例2-3
Figure A20058003967800221
实施例   R3   R4   R5     MS(MALDI负模式)   UVλmax/ε(λmax)[nm；L/gcm]
2   Ph   Me   Me     283[M-H]-   343/87
3   Ph   Me   Ph     345[M-H]-   350/40
实施例4
68份实施例1中所得化合物和25份四水合乙酸镍在1170份乙醇中回流30分钟。冷却后将沉淀的产物过滤并用乙醇洗涤，得到71份双[3-(1-苄基-5-甲基-3-氧代-2-对甲苯基-2，3-二氢-1H-吡唑-4-基)-4-羟基-环丁-3-烯-1，2-二酮]镍。
Figure A20058003967800222
MS(MALDI负模式)：713[M-苄基]；
UV-V是(MeOH)λmax：338nm；ε(λmax)：49Lg-1.cm-1；
分解点(TGA)：297℃；
在2，2，3，3-四氟-卜丙醇中的溶解度：＞30g/L.
实施例5-12
根据实施例4所述方法合成化合物。起始物料分别为实施例1-3中得到的化合物。
实施例   R3   R4   R5     n     M   电荷(反离子) UVλmax/ε(λmax)[nm；L/gcm]
5   Ph   Me   Me     2     Ni   - 342/82
6   Ph   Me   Me     2     Cu   - 340/65
7   Ph   Me   Me     2     Co   - 340/50
8   Ph   Me   Me     3     Cr   - 331/46
9   Ph   Me   Me     2     Zn   - 340/63
10   Ph   Me   Me     2     Al   +1(Cl-) 337/64
11   Ph   Me   Me     3     Zr   +1(Cl-) 343/65
12   Ph   Me   Ph     2     Ni   - 350/20
应用实施例
研究了新方形酸金属络合物染料的光和热性质。染料在所需波长显示高吸收。此外，吸收光谱的形状(仍然对磁盘反射率和干净标记边缘的形成至关重要)由一个包括在330-500纳米范围的主带组成。
发现其光稳定性与通常用于光学数据记录的使用淬灭剂稳定化的商用染料是相当的。
在所需温度范围内的热分解的尖锐阈值成为设想适于用于光学数据记录的光学层中的新的方形酸金属络合物染料的特征。
总之，本发明的新方形酸金属络合物染料工业上主要用于光学数据记录染料，特别是蓝色激光范围内的下一代光学数据记录介质。

Claims (10)

1.一种式(I)的染料化合物或其一种互变异构形式，
Figure A2005800396780002C1
其中
X表示去质子化的羟基(-OH)、硫醇(-SH)或胺(NHR1)，其中R1表示氢、C1-12烷基(未取代或者被以下基团取代：羟基(-OH)、C6-12芳基、卤素、-NR9R10′，其中R9和R10独立地为氢、C1-12烷基或C6-12芳基)、苄基或C6-12芳基；
Y表示氧、硫或亚胺-氮N-R2，其中R2表示氢、C1-12烷基(未取代或者被以下基团取代：羟基(-OH)、C6-12芳基、卤素、-NR′R″，其中R′和R″独立地为氢、C1-12烷基或C6-12芳基)、苄基或C6-12芳基；
z表示-2到+2的电荷；
An-表示选自以下的阴离子配对物：无机阴离子，例如碘、氟、溴、氯、高氯酸盐、六氟锑酸盐、六氟磷酸盐、四氟硼酸盐、四苯基硼酸盐，或有机阴离子，例如二氰基酰胺(N(CN)2)或者三氟甲磺酰亚胺(N(SO3CF3)2)；或An-还可为阴离子偶氮金属络合物，
M表示金属离子；
A为五元或六元芳香或杂芳香环，其可被进一步取代或退火，
n表示1-4的整数。
2.根据权利要求1的式(I)所示染料化合物，其中
X表示去质子化的羟基(-OH)或硫醇(-SH)；
Y表示氧或硫；
z表示0到+1的电荷；
An-表示选自以下的阴离子配对物：无机阴离子，例如氯、高氯酸盐、六氟锑酸盐、六氟磷酸盐、四氟硼酸盐、四苯基硼酸盐，或有机阴离子，例如二氰基酰胺(N(CN)2)或者三氟甲磺酰亚胺(N(SO3CF3)2)；或
An-还可为阴离子偶氮金属络合物，
M表示金属离子，选自Ca，Sr，Ba，Al，Ga，In，Sc，Y，Ti，Zr，V，Nb，Ta，Cr，Mo，W，Mn，Fe，Ru，Os，Co，Rh，Ir，Ni，Pd，Pt，Cu，Ag，Au，Zn，Cd，Hg，La，Ce，Pr，Nd，Pm，Sm，Eu，Gd，Tb，Dy，Ho，Er，Tm，Yb，Lu；
n表示1-4的整数
选择A以形成以下基团中的一种或其互变异构形式的一种：
其中
R3和R4彼此独立地表示氢；C1-8烷基，其中所述烷基可未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；CX3，其中X可为氯、氟、溴；C6-12芳基，其可未取代或者被C1-8烷基、羟基(-OH)、硝基(-NO2)、氰基(-CN)、卤素、C6-12芳基、-NR9R10或者C1-C8烷氧基(-OR)取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；
R5-R8各自独立地表示氢、氰基(-CN)、卤素、硝基(-NO2)、羟基、直链或支链C1-8烷氧基(-OR)，其中烷基(R)未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；氨基(NR9R10)，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基，或者其中R9和R10可形成可含有其它杂原子的五元或六元环；直链或支链C1-8烷基，其中烷基可未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；CX3，其中X可为氯、氟、溴；直链或支链C1-8烷硫基，其中烷基未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；C6-C12芳基，其未取代或者被C1-8烷基、羟基(-OH)、硝基(-NO2)、氰基(-CN)、卤素、C6-12芳基、-NR9R10或者C1-C8烷氧基(-OR)取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基。
3.根据权利要求1的式(I)所示染料化合物，其中
X表示去质子化的羟基(-OH)；
Y表示氧；
z表示0到+1的电荷；
An-表示氯；
M表示金属离子，选自Al，Y，Zr，Cr，Fe，Co，Ni，Cu，Zn，Yb；
n表示2-3的整数；
选择A以形成以下基团的一种或其互变异构形式的一种：
Figure A2005800396780004C1
其中
R3和R4彼此独立地表示氢；C1-8烷基，其中所述烷基可未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；C6-C12芳基，其可未取代或者被C1-8烷基、羟基(-OH)、硝基(-NO2)、氰基(-CN)、卤素、C6-12芳基、-NR9R10或者C1-C8烷氧基(-OR)取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；
R5-R8各自独立地表示氢、氰基(-CN)、卤素、硝基(-NO2)、羟基、直链或支链C1-8烷氧基(-OR)，其中烷基(R)未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；氨基(NR9R10)，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基，或者R9和R10可形成可含有其它杂原子的五元或六元环；直链或支链C1-8烷基，其中烷基可未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；CX3，其中X可为氯、氟、溴；直链或支链C1-8烷硫基，其中烷基未取代或者被C1-8烷基、羟基(-OH)、C6-12芳基或-NR9R10取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基；C6-12芳基，其未取代或者被C1-8烷基、羟基(-OH)、硝基(-NO2)、氰基(-CN)、卤素、C6-12芳基、-NR9R10或者C1-C8烷氧基(-OR)取代，其中R9和R10独立地为氢、C1-8烷基或C6-12芳基。
4.根据权利要求1的式(I)所示染料化合物，其中染料化合物为式(II)化合物，
Figure A2005800396780005C1
其中
z表示0到+1的电荷；
An-表示氯；
M表示金属离子，选自Al，Zr，Cr，Co，Ni，Cu，Zn；
n表示2-3的整数；
R3表示苯基或对甲苯基，
R4表示甲基或苄基，
R5表示甲基或苯基。
5.一种光学层，包括至少一种根据权利要求1-4所定义的式(I)染料化合物或至少两种根据权利要求1-4所定义的式(I)染料化合物的混合物。
6.一种制备根据权利要求5的光学层的方法，包括以下步骤：
(a)提供衬底，
(b)将权利要求1-4所定义的式(I)染料化合物或式(I)染料化合物混合物溶于有机溶剂以形成溶液，
(c)将溶液(b)涂布在衬底(a)上；
(d)蒸发溶剂以形成染料层。
7.根据权利要求6的方法，其中衬底为聚碳酸酯(PC)或聚甲基丙烯酸甲酯(PMMA)。
8.根据权利要求6的方法，其中有机溶剂选自C1-8醇、卤代C1-8醇、C1-8酮、C1-8醚、卤代的C1-4烷烃或酰胺。
9.根据权利要求6的方法，其中C1-8醇或卤代C1-8醇选自：甲醇、乙醇、异丙醇、二丙酮醇(DAA)、2，2，3，3-四氟丙醇、三氯乙醇、2-氯乙醇、八氟戊醇或六氟丁醇；
C1-8酮选自丙酮、甲基异丁酮、甲乙酮或3-羟基-3-甲基-2-丁酮；
卤代的C1-4烷烃选自氯仿、二氯甲烷或1-氯丁烷；并且
酰胺选自二甲基甲酰胺或二甲基乙酰胺。
10.包括根据权利要求5的光学层的光记录介质。
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