CN102675304B - 花青化合物、使用该化合物的光学记录材料和光学记录介质 - Google Patents

花青化合物、使用该化合物的光学记录材料和光学记录介质 Download PDF

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CN102675304B
CN102675304B CN201210063842.2A CN201210063842A CN102675304B CN 102675304 B CN102675304 B CN 102675304B CN 201210063842 A CN201210063842 A CN 201210063842A CN 102675304 B CN102675304 B CN 102675304B
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冈田光裕
矢野亨
滋野浩一
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Adeka Corp
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Abstract

本发明的花青化合物是由下述通式(I)表示的花青化合物，并且适合于用激光进行记录和再生的光学记录介质的记录层中所使用的光学记录材料。本发明的花青化合物显示出用于实现特别能对应于高速记录的感度的适合的热行为。通式(I)中，环A和环B表示苯环或萘环，R1和R2各自独立地表示碳原子数为1～4的烷基或者苄基，并且R1和R2中的至少一个是苄基；X表示O或S；Y1和Y2各自独立地表示甲基、乙基或丁基；Z表示氢原子，Anm-表示六氟化磷阴离子，p表示保持电荷为中性的系数

Description

花青化合物、使用该化合物的光学记录材料和光学记录介质
技术领域
本发明涉及新型的花青化合物、含有该花青化合物而成的光学记录材料、以及使用了该光学记录材料的光学记录介质。该花青化合物不仅适合作为光学元件，特别适合于用激光进行记录和再生的光学记录介质的记录层中所使用的光学记录材料，而且还可以用作图像显示装置的滤光器中使用的光吸收剂。
背景技术
将在波长为500～700nm的范围内具有高强度吸收的化合物、特别是最大吸收(λmax)为550～620nm的化合物用作DVD-R等的光学记录介质的光学记录层或液晶显示器(LCD)、等离子显示板(PDP)、电致发光显示器(ELD)、阴极管显示器(CRT)、荧光显示管和场致发射型显示器等图像显示装置的滤光器的光学元件。
作为上述光学元件，大量研究了感度高的具有吲哚环的花青化合物。该花青化合物，特别是作为以DVD-R为代表的光学记录介质的记录元件，由于具有能与记录高速化相对应的优点，因此公开的例子很多，例如在下述专利文献1～5等中被公开。另外，在专利文献6中记载了在吲哚骨架3位引入了苄基的花青化合物。
但是，以往的花青类化合物在热分解性方面有问题。作为进行高速记录的光学记录介质的记录元件，优选的是分解温度低的材料，但是公开的上述花青类化合物在这方面并不具有充分的特性。
专利文献1：特开平10-278426号公报
专利文献2：特开平11-227331号公报
专利文献3：特开平11-277904号公报
专利文献4：特表2001-506933号公报
专利文献5：特开2002-52829号公报
专利文献6：特开2003-231359号公报
发明内容
因此，本发明的目的在于提供显示出更适合于光学记录用途的热行为的新型花青化合物、含有该化合物的光学记录材料和使用了该光学记录材料的光学记录介质。
本发明者等考虑到热分解行为的适当化和吸收波长的适当化对于实现可对应于高速记录的感度是有效的，并进行了反复研究，结果发现具有特定的分子结构的花青类化合物可以解决上述课题。
本发明是基于上述认识而提出的，提供了由下述通式(I)表示的化合物。
另外，本发明提供了在基体上形成了光学记录层而得到的光学记录介质的该光学记录层中所使用的、含有上述花青化合物而成的光学记录材料。
此外，本发明提供了在基体上形成了由上述光学记录材料构成的薄膜而得到的光学记录介质。
[化学式1]
Figure BDA0000142537630000021
(式中，环A和环B表示苯环或萘环，R1和R2各自独立地表示碳原子数为1～4的烷基或者苄基，并且R1和R2中的至少一个是苄基；X表示O或S；Y1和Y2各自独立地表示甲基、乙基或丁基；Z表示氢原子，Anm-表示六氟化磷阴离子，p表示保持电荷为中性的系数。)
附图说明
图1-a表示在实施例1中得到的化合物No.2的六氟化磷盐的1H-NMR谱图。
图1-b是图1-a的部分放大图。
图1-c是图1-a的部分放大图。
图2-a是在实施例2中得到的化合物No.8的六氟化磷盐的1H-NMR谱图。
图2-b是图2-a的部分放大图。
图2-c是图2-a的部分放大图。
具体实施方式
上述通式(I)所示的本发明的花青化合物是在特定部位具有可以具有取代基的苄基的新型化合物，与在DVD-R用途的光学记录材料中所使用的其它花青类化合物相比，具有分解温度更低、吸收波长适当的特征。
在上述通式(I)中，作为环A和环B所表示的可以具有取代基的苯环或萘环的取代基，可以列举出氟、氯、溴、碘等卤代基；甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基、戊基、异戊基、叔戊基、己基、环己基、庚基、异庚基、叔庚基、正辛基、异辛基、叔辛基、2-乙基己基等烷基；苯基、萘基、2-甲基苯基、3-甲基苯基、4-甲基苯基、4-乙烯基苯基、3-异丙基苯基等芳基；甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基等烷氧基；甲硫基、乙硫基、丙硫基、异丙硫基、丁硫基、仲丁硫基、叔丁硫基等烷基硫基；硝基、氰基等。
在上述通式(I)中，作为R1或R2所表示的碳原子数为1～4的烷基，可以列举出甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基等。
在R1或R2表示的基团中，至少一个是可以具有取代基的苄基。该苄基可以具有的取代基数是1或2。作为该取代基，可列举出氟、氯、溴、碘等卤代基；甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基、戊基、异戊基、叔戊基、己基、环己基、庚基、异庚基、叔庚基、正辛基、异辛基、叔辛基、2-乙基己基等烷基；这些烷基的卤素取代物；甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基等烷氧基；这些烷氧基的卤素取代物；甲硫基、乙硫基、丙硫基、异丙硫基、丁硫基、仲丁硫基、叔丁硫基等烷硫基；硝基；氰基；羟基等，当该取代基大时，花青化合物的摩尔吸光系数变小，有时给感度带来影响，所以作为具有取代基的苄基，优选为由下述通式(II)表示的基团。
[化学式1]
Figure BDA0000142537630000041
(式中，m表示1～2的整数，X1表示羟基、卤素基、氰基、硝基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的烷氧基、或碳原子数为1～4的卤代烷氧基，当m是2时，两个X1可以相同也可以不同。)
在上述通式(II)中，作为X1表示的卤代基，可列举出氟、氯、溴、碘等，作为碳原子数为1～4的烷基，可列举出甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基，作为碳原子数为1～4的卤代烷基，可列举出一氯甲基、二氯甲基、三氯甲基、一溴甲基、二溴甲基、三溴甲基、一氟甲基、二氟甲基、三氟甲基、全氟乙基、全氟丙基、全氟丁基等，作为碳原子数为1～4的烷氧基，可列举出甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基等，作为碳原子数为1～4的卤代烷氧基，可列举出一氯甲氧基、二氯甲氧基、三氯甲氧基、一溴甲氧基、二溴甲氧基、三溴甲氧基、一氟甲氧基、二氟甲氧基、三氟甲氧基、全氟乙氧基、全氟丙氧基、全氟丁氧基等。
作为上述通式(I)中Y1或Y2所表示的碳原子数为1～30的有机基，没有特别的限定，例如可以列举出甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基、戊基、异戊基、叔戊基、己基、环己基、环己基甲基、2-环己基乙基、庚基、异庚基、叔庚基、正辛基、异辛基、叔辛基、2-乙基己基、壬基、异壬基、癸基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基等烷基；乙烯基、1-甲基乙烯基、2-甲基乙烯基、丙烯基、丁烯基、异丁烯基、戊烯基、己烯基、庚烯基、辛烯基、癸烯基、十五烯基、1-苯基丙烯-3-基等链烯基；苯基、萘基、2-甲基苯基、3-甲基苯基、4-甲基苯基、4-乙烯基苯基、3-异丙基苯基、4-异丙基苯基、4-丁基苯基、4-异丁基苯基、4-叔丁基苯基、4-己基苯基、4-环己基苯基、4-辛基苯基、4-(2-乙基己基)苯基、4-硬脂基苯基、2，3-二甲基苯基、2，4-二甲基苯基、2，5-二甲基苯基、2，6-二甲基苯基、3，4-二甲基苯基、3，5-二甲基苯基、2，4-二叔丁基苯基、环己基苯基等烷芳基；苄基、苯乙基、2-苯基丙烷-2-基、二苯基甲基、三苯基甲基、苯乙烯基、肉桂基等芳烷基，以及这些烃基被醚键和/或硫醚键插入的那些基团，例如可以列举出2-甲氧基乙基、3-甲氧基丙基、4-甲氧基丁基、2-丁氧基乙基、甲氧基乙氧基乙基、甲氧基乙氧基乙氧基乙基、3-甲氧基丁基、2-苯氧基乙基、2-甲硫基乙基、2-苯硫基乙基；而且，这些基团还可以被烷氧基、链烯基、硝基、氰基、卤原子等取代。
关于上述Y1和Y2，如果作为取代基的这些基团较大，则花青化合物的摩尔吸光系数变小，有时对感度有影响，因此，优选为碳原子数为1～8的烃基，更优选为碳原子数为1～8的烷基。
而且，当X是NY是时，由Y表示的碳原子数为1～30的有机基与上述Y1和Y2相同。
上述通式(I)中，作为Z表示的卤原子，可列举出氟、氯、溴、碘。
另外，上述通式(I)中，作为由Anm-表示的阴离子，例如，作为一价阴离子，可以列举出氯阴离子、溴阴离子、碘阴离子、氟阴离子等卤素阴离子；高氯酸阴离子、氯酸阴离子、硫氰酸阴离子、六氟化磷阴离子、六氟化锑阴离子、四氟化硼阴离子等无机系阴离子；苯磺酸阴离子、甲苯磺酸阴离子、三氟甲烷磺酸阴离子、二苯基胺-4-磺酸阴离子、2-氨基-4-甲基-5-氯代苯磺酸阴离子、2-氨基-5-硝基苯磺酸阴离子等有机磺酸阴离子；辛基磷酸阴离子、十二烷基磷酸阴离子、十八烷基磷酸阴离子、苯基磷酸阴离子、壬基苯基磷酸阴离子、2，2’-亚甲基双(4，6-二叔丁基苯基)膦酸阴离子等有机膦酸系阴离子等；作为二价阴离子，例如可以列举出苯二磺酸阴离子、萘二磺酸阴离子等。另外，根据需要也可以使用具有使处于激发态的活性分子去激发(淬灭)功能的淬灭阴离子或和在环戊二烯基环上具有羧基、膦酸基、磺酸基等阴离子性基团的二茂铁、二茂钌等金属茂化合物阴离子等。
作为上述的淬灭阴离子，例如可以列举出由下述通式(A)或(B)表示的、在特开昭60-234892号公报、特开平5-43814号公报、特开平6-239028号公报、特开平9-309886号公报、特开平10-45767号公报等中记载的阴离子。
[化学式3]
Figure BDA0000142537630000071
(式中，M表示镍原子或铜原子；R5和R6表示卤原子、碳原子数为1～8的烷基、碳原子数为6～30的芳基或-SO2-Z基，Z表示烷基、可以被卤原子取代的芳基、二烷基氨基、二芳基氨基、哌啶基或吗啉基；a和b分别表示0～4。另外，R7、R8、R9和R10各自独立地表示烷基、烷基苯基、烷氧基苯基或卤代苯基。)
作为上述通式(I)所示的本发明的花青化合物的具体例子，可以列举出下述化合物No.1～27。另外，在以下例子中，以省略了阴离子的花青化合物阳离子来表示。
[化学式4]
Figure BDA0000142537630000081
[化学式5]
[化学式6]
Figure BDA0000142537630000101
在上述花青化合物之中，由于作为光学记录材料的热行为更为良好，因此优选为下述化合物：构成键合有可以具有取代基的苄基的吲哚骨架的环(上述通式(I)中的环A)为萘环(例如化合物No.1～12、19～22、24～27)、特别是在吲哚环的e面上缩合了苯环的化合物(例如化合物No.1～4、7～12、19～22、25～27)；上述通式(I)中的环B为苯环(例如，化合物No.1～18、20、21、23～27)的化合物，更优选上述环A为萘环而且上述环B为苯环的化合物(例如化合物No.1～12、20、21、24～27)。这可以认为是由于可以具有取代基的苄基和苯并吲哚环的立体位阻所导致的环结构的歪斜变得更大而引起的。
上述通式(I)所示的本发明的花青化合物并不受到其制备方法的限制。该花青化合物，例如可以通过使作为中间体的2-甲基噻唑鎓盐衍生物和2-甲基吲哚四级盐衍生物与N，N’-二苯基甲脒等桥联剂反应而得到。另外，可以具有取代基的苄基可以在得到作为中间体的2-甲基吲哚四级盐衍生物的过程中引入，也可以将芳基肼作为起始物质、在通过4位具有可以具有取代基X1的苯基的2-丁酮衍生物形成吲哚环时引入；也可在使吲哚环与卤代甲基苯衍生物反应时引入。Y1或Y2可以通过与芳胺衍生物或吲哚环的NH发生反应的Y1-D或Y2-D(D是氯、溴、碘等卤代基、苯磺酰氧基、4-甲基苯磺酰氧基、4-氯代苯磺酰氧基等磺酰氧基)引入。另外，作为在4位具有可以具有取代基X1的苯基的2-丁酮衍生物可以通过使丙酮和可以具有取代基X1的苯甲醛反应而容易地获得。作为得到本发明的花青化合物的具体方法的一个例子，可以列举出下述[化学式7]所示的路线。
[化学式7]
Figure BDA0000142537630000111
(式中，环A、环B、R2、Y1、Y2、X、X1和m与上述通式(I)和(II)相同，An1 -1、An2 -1和An-表示阴离子。)
本发明的花青化合物起到光学元件的功能，特别适合于光学记录介质的光学记录层。含有本发明的花青化合物的光学记录层使用含有本发明的花青化合物的光学记录材料在基体上以薄膜的形式形成。另外，本发明的光学记录材料包括本发明的花青化合物本身、以及本发明的花青化合物与后述的有机溶剂和/或各种化合物的混合物。
对于使用了本发明的光学记录材料的光学记录介质的光学记录层的形成方法，没有特别的限制。一般地讲，可使用湿式涂布法，即通过旋涂、喷涂、浸渍等方法在基体上涂布在下述有机溶剂中溶解了本发明的花青化合物和根据需要溶解的后述的各种化合物而得到的溶液，上述溶剂是：甲醇、乙醇等低级醇类；甲基溶纤剂、乙基溶纤剂、丁基溶纤剂、丁基二甘醇等醚醇类；丙酮、甲基乙基酮、甲基异丁基酮、环己酮、双丙酮醇等酮类；乙酸乙酯、醋酸丁酯、醋酸甲氧基乙酯等酯类；丙烯酸乙酯、丙烯酸丁酯等丙烯酸酯类；2，2，3，3-四氟丙醇等氟代醇类；苯、甲苯、二甲苯等烃类；二氯甲烷、二氯乙烷、氯仿等氯代烃类等。作为其它的方法，可以列举出蒸镀法、溅射法等。
使用本发明的光学记录材料而形成的上述光学记录层的厚度通常适合的是0.001～10μ，优选为0.01～5μ的范围。
另外，在光学记录介质的光学记录层中含有本发明的光学记录材料时，该光学记录层中本发明的花青化合物的含量优选为50～100质量％。为了形成具有这种含量的花青化合物的光学记录层，本发明的光学记录材料优选以本发明的光学记录材料中所含有的固体成分为基准、含有50～100质量％的本发明的花青化合物。
另外，上述光学记录层除了本发明的花青化合物之外，根据需要还可以含有：其他花青类化合物、偶氮类化合物、酞菁类化合物、卟吩类化合物等可用于光学记录层的化合物；聚乙烯、聚酯、聚苯乙烯、聚碳酸酯等树脂类；表面活性剂；抗静电剂；润滑剂；阻燃剂；受阻胺等自由基捕获剂；二茂铁衍生物等凹坑(pit)形成促进剂；分散剂；抗氧化剂；交联剂；耐光性赋予剂等。此外，上述光学记录层可以含有芳香族亚硝基化合物、铵(aminium)化合物、亚胺鎓盐化合物(iminium)、二亚胺鎓盐化合物、过渡金属螯合物等作为单线态氧等的淬灭剂。
这些各种化合物在上述光学记录层中优选以0～50质量％的范围使用。为此，在本发明的光学记录材料中，这些各种化合物的含量，以本发明的光学记录材料中所含有的固体成分为基准，优选为0～50质量％。
对于设置有上述光学记录层的上述基体的材料，只要对写入(记录)光和读取(再生)光实质上是透明的就可以，没有特别的限制，例如，可以使用聚甲基丙烯酸甲酯、聚对苯二甲酸乙二酯、聚碳酸酯等树脂、玻璃等。另外，根据用途，其形状可以做成带状、筒状、皮带状、圆盘等任意形状。
另外，在上述的光学记录层上，也可使用金、银、铝、铜等通过蒸镀法或溅射法形成反射膜，也可以形成由丙烯酸树脂、紫外线固化性树脂等得到的保护层。
本发明的光学记录材料适合于在记录、再生中使用半导体激光的光学记录介质，特别适合于高速记录类型的DVD-R等光盘。
实施例
下面，根据实施例和评价例来更详细地说明本发明。但是，本发明不受到以下实施例等的任何限制。
[实施例1]化合物No.2的六氟化磷盐的制造
在反应烧瓶中加入下述[化学式8]所示的吲哚衍生物A 2.9g(0.005mol)、由下述[化学式9]所示的合成路线得到的中间体B 2.0g(0.005mol)、以及吡啶4.2g(0.05mol)，升温至40℃，搅拌均匀。滴加醋酸酐0.8g(0.0075mol)使其反应4小时。冷却后，用氯仿40g/水30g洗涤两次，接着，用六氟化磷钾3g(0.015mol)水溶液进行两次盐交换，然后进行两次水洗。用蒸发器脱去溶剂后，用甲醇35g进行析晶。经过滤、甲醇洗涤、真空干燥，获得灰色固体2.6g(收率为74％)。对得到的灰色固体进行分析，结果确定为是目标物(化合物No.2的六氟化磷盐)。分析结果如下。
[化学式8]
Figure BDA0000142537630000141
分析结果
·光学特性(氯仿，1.01×10-6mol/L)
λmax：584nm、ε：1.2×105
·吸热温度(在氮气中在10℃/分钟的升温条件下通过TG/DTA测定的吸热峰最大值)
213.1℃
·分子量(TOF-质谱分析)
660.7
·1H-NMR(溶剂：DMSO)
图1表示1H-NMR谱。
[实施例2]化合物No.8的六氟化磷盐的制造
在反应烧瓶中加入上述吲哚衍生物A 16.5g、下述[化学式10]所示的中间体C 8.7g(0.03mol)、以及吡啶47.4g(0.6mol)，并搅拌。在室温下滴加醋酸酐4.6g(0.045mol)，使其反应15小时。用氯仿150g/水100g洗涤两次后，用六氟化磷钾5.5g(0.03mol)水溶液进行一次盐交换，接着进行两次水洗。用蒸发器脱去溶剂，获得粗品。对得到的粗品进行柱精制(醋酸乙酯∶己烷＝1.5∶1，原点甲醇萃取)，通过浓缩获得紫色固体1.8g。另外，用二甲基乙酰胺/甲醇进行重结晶，获得紫色固体1.3g(收率为7％)。对得到的紫色固体进行分析，结果确定为是目标物(化合物No.8的六氟化磷盐)。分析结果如下。
[化学式10]
Figure BDA0000142537630000151
分析结果
·光学特性(氯仿，9.81×10-6mol/L)
λmax：547nm、ε：1.14×105
·吸热温度(在氮气中在10℃/分钟的升温条件下通过TG/DTA测定的吸热峰最大值)
218.4℃
·分子量(TOF-质谱分析)
616.6
·1H-NMR(溶剂：DMSO)
图2表示1H-NMR谱。
[评价例]
对由上述实施例得到的化合物No.2和8以及下面的[化学式11]所示的比较化合物1，在氮气流中进行示差热分析，测量热分解温度。热分解温度是在氮气中在10℃/分的升温条件下得到的DTA的放热最高峰的温度。结果示于表1中。
[化学式11]
Figure BDA0000142537630000161
表1
从上述表1的结果可以确认，本发明的花青化合物的热分解温度较低。这表示本发明的花青化合物作为光学记录材料适合用于高速记录中。
[实施例3]
将化合物No.2的六氟化磷盐溶解在2，2，3，3-四氟丙醇中，以使其浓度为1质量％，从而获得光学记录材料。在直径为12厘米的聚碳酸酯圆盘基板上涂布钛螯合化合物(T-50：日本曹达公司制)，然后进行水解，从而设置了基底层(0.01μ)，在该设置了基底层的基板上，以旋涂法涂布上述光学记录材料(在旋转数为2000rpm下旋转涂布1分钟)，获得光学记录介质。对于该光学记录介质，进行透射光UV光谱的测量，结果是λmax为598nm，确认了上述光学记录材料适合作为DVD-R用的光学记录材料。
[实施例4]
除了使用化合物No.8的六氟化磷盐来代替化合物No.2的六氟化磷盐以外，与实施例3相同地制作光学记录材料，并使用该光学记录材料获得光学记录介质。对于该光学记录介质，进行透射光UV光谱的测量，结果是λmax为558nm，确认了上述光学记录材料适合作为DVD-R用的光学记录材料。
根据本发明，可以提供显示出更加适合光学记录用途的热行为的新型花青化合物、含有该化合物的光学记录材料、和使用了该光学记录材料的光学记录介质。

Claims (8)

1.一种由下述通式(I)表示的花青化合物，
式中，环A和环B表示苯环或萘环，R1和R2各自独立地表示碳原子数为1～4的烷基或者苄基，并且R1和R2中的至少一个是苄基；X表示O或S；Y1和Y2各自独立地表示甲基、乙基或丁基；Z表示氢原子，Anm-表示六氟化磷阴离子，p表示保持电荷为中性的系数。
2.权利要求1记载的花青化合物，其中，所述通式(I)中的环B是苯环。
3.权利要求1或2记载的花青化合物，其中，所述通式(I)中的X是S。
4.权利要求1或2记载的花青化合物，其中，所述通式(I)中的X是O。
5.权利要求1或2记载的花青化合物，其中，所述通式(I)中的环A是萘环。
6.权利要求1或2记载的花青化合物，其中，所述通式(I)中的R1和R2之中的任一个是甲基。
7.一种光学记录材料，其含有权利要求1～6任何一项记载的花青化合物，并被用于在基体上形成了光学记录层而得到的光学记录介质的该光学记录层中。
8.一种光学记录介质，其是在基体上形成了由权利要求7记载的光学记录材料组成的薄膜而得到的。
CN201210063842.2A 2004-11-25 2005-10-13 花青化合物、使用该化合物的光学记录材料和光学记录介质 Expired - Fee Related CN102675304B (zh)

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