CN101035867B - 花青化合物和光学记录材料 - Google Patents

花青化合物和光学记录材料 Download PDF

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CN101035867B
CN101035867B CN2005800342046A CN200580034204A CN101035867B CN 101035867 B CN101035867 B CN 101035867B CN 2005800342046 A CN2005800342046 A CN 2005800342046A CN 200580034204 A CN200580034204 A CN 200580034204A CN 101035867 B CN101035867 B CN 101035867B
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滋野浩一
矢野亨
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Abstract

本发明的花青化合物如下述通式(I)所示,其分解行为适合光学记录材料,所述光学记录材料用于实现高速记录的光学记录介质的光学记录层中。
Figure 200580034204.6_AB_0
(式中,环A和环B表示可以具有取代基的苯环或萘环,X表示O、S、Se、CR 3R 4或NY,R 1和R 2中的至少一个表示通式(II)或(III)所示的基团,当仅有一个是通式(II)或(III)所示的基团时,另一个表示碳原子数为1~30的有机基团,R 3和R 4表示碳原子数为1~30的有机基团,Y表示氢原子或碳原子数为1~30的有机基团,Y 1和Y 2中的至少一个表示通式(IV)所示的基团,当仅有一个是通式(IV)所示的基团时,另一个表示氢原子或碳原子数为1~30的有机基团,Z表示氢原子、卤原子或氰基,An m-表示m价的阴离子,m表示1或2的整数,p表示保持电荷为中性的系数。)。

Description

花青化合物和光学记录材料
技术领域
本发明涉及新型的花青化合物和含有该花青化合物的光学记录介质。该花青化合物除了适用于光学记录材料以外,还可以用于图像显示设备的滤光器用光吸收材料。
背景技术
在550~620nm范围内具有高强度吸收的化合物,特别是最大吸收(λmax)在550~620nm的化合物被作为光学记录材料使用,用于形成DVD-R等光学记录介质的光学记录层。
作为上述光学记录材料,具有吲哚环的花青化合物具有感度高、可以对应记录的高速化的优点,因而有许多报道的例子。例如在专利文献1和2中,报道了在N侧链上引入含茂金属基的低温分解性花青化合物,专利文献3中,报道了在3位上引入苄基的低温分解性花青化合物。此外,在专利文献1中,记载了通过使用高氯酸阴离子作为花青化合物的阴离子成分,可以实现更好的低温分解性。
此外,用于光学记录介质的光学记录层的光学记录材料若分解时的放热较大,则由于记录凹坑(pit)的热干扰而使记录性能变差。因此,作为光学记录材料,不仅要求分解温度低,还要求分解热小。例如,使用了在低温分解性方面有效的高氯酸阴离子的花青化合物由于分解时的放热较大,有时使得光学记录介质的跳动(jitter)性能变差。
专利文献1:特开2003-171571号公报
专利文献2:特开2004-195765号公报
专利文献3:特开2003-231359号公报
发明内容
因而,本发明旨在提供一种其分解行为适合光学记录材料的花青化合物以及含有该花青化合物的光学记录材料,所述光学记录材料用于可实现高速记录的光学记录介质的光学记录层中。
本发明者们经过反复研究发现,具有特定的阳离子结构的花青化合物具有适合于光学记录材料的良好的热特性。
本发明是在上述发现的基础上完成的,提供一种如下述通式(I)所示的花青化合物、以及用于在基体上形成有光学记录层的光学记录介质的该光学记录层中并含有所述花青化合物的光学记录材料。
Figure GSB00000131496800021
(式中,环A和环B表示可以有取代基的苯环或萘环,X表示O、S、Se、CR3R4或NY,R1和R2中的至少一个表示下述通式(II)或(III)所示的基团,当仅有一个是表示下述通式(II)或(III)所示的基团时,另一个表示碳原子数为1~30的有机基团,R3和R4表示碳原子数为1~30的有机基团,Y表示氢原子或碳原子数为1~30的有机基团,Y1和Y2中的至少一个表示下述通式(IV)所示的基团,当仅有一个是表示下述通式(IV)所示的基团时,另一个表示氢原子或碳原子数为1~30的有机基团,Z表示氢原子、卤原子或氰基,Anm-表示m价的阴离子,m表示1或2的整数,p表示保持电荷为中性的系数。)
(通式(II)中,E和G之间的键是双键或三键,E表示碳原子,G表示碳原子、氧原子或氮原子,x、y和z表示0或1,R5表示氢原子、卤原子、可被卤原子取代的碳原子数为1~4的烷基或可被卤原子取代的碳原子数为1~4的烷氧基,R6、R7和R8分别独立地表示氢原子、卤原子或可被卤原子取代的碳原子数为1~4的烷基,R6和R8可以结合形成环结构;通式(III)中,E’和G’之间的键是双键,E’表示碳原子,G’表示碳原子、氧原子或氮原子,含E’和G’的环表示可含杂原子的5元环、含杂原子的6元环、苯环、萘环、喹啉环、异喹啉环、蒽环或蒽醌环,所述含E’和G’的环可被羟基、卤原子、硝基、氰基、烷基、烷氧基取代;通式(IV)中,R9~R17表示氢原子或可被卤原子取代且链中的亚甲基可被-O-或-CO-取代的碳原子数为1~4的烷基,M表示Fe、Co、Ni、Ti、Cu、Zn、Zr、Cr、Mo、Os、Mn、Ru、Sn、Pd、Rh或Pt,J表示直接键合或碳原子数为1~8的亚烷基,所述亚烷基中的亚甲基可以被-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-取代。)
附图说明
图1是在实施例1中得到的本发明的花青化合物(化合物No.4的六氟化磷盐)的1H-NMR谱图。
具体实施方式
上述通式(I)所示的本发明的花青化合物的特征在于:在吲哚骨架的3位上具有特定结构的基团,在N侧链上具有其它的特定的基团,与DVD-R用途的光学记录材料中使用的现有的花青类化合物相比具有下述特征:分解温度更低,能够对应高速的记录。
上述通式(I)中,作为环A和环B所示的可以有取代基的苯环或萘环的所述取代基,可以列举出氟、氯、溴、碘等卤素基;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、三氟甲基等可被卤原子取代的烷基;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、三氟甲氧基等可被卤原子取代的烷氧基;甲硫基、乙硫基、丙硫基、异丙硫基、丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基等烷基硫基;硝基、氰基等。
上述通式(I)中,R1~R4、Y、Y1或Y2所示的碳原子数为1~30的有机基团没有特别的限制,可以列举出例如甲基、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-硬脂酰基苯基、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、环己基苯基等烷基芳基;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、肉桂基等芳基烷基,此外可以列举出上述烃基被醚键和/或硫醚键中断而得到的基团,例如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;而且这些基团可以被烷氧基、链烯基、硝基、氰基、卤原子等取代。
对于上述通式(I)的R1~R4,如果作为取代基的这些基团较大,则有时花青化合物的摩尔吸光系数变小,影响感度,此外,由于空间位阻,有可能会使花青化合物的生产效率显著降低,因此,优选如下所示的基团。另外,对于R1和R2,优选至少一个为上述通式(III)所示基团的、下述的可有取代基的苄基。
甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基等烷基,特别优选碳原子数为1~4的烷基。
可有取代基的苄基。作为所述取代基,可以列举出例如羟基;氟、氯、溴、碘等卤素基;氰基;硝基;甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基等碳原子数为1~4的烷基;氯甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、全氟乙基、全氟丙基、全氟丁基等碳原子数为1~4的卤代烷基;甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基等碳原子数为1~4的烷氧基;氯甲氧基、二氯甲氧基、三氯甲氧基、溴甲氧基、二溴甲氧基、三溴甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、全氟乙氧基、全氟丙氧基、全氟丁氧基等碳原子数为1~4的卤代烷氧基等。
此外,R3和R4还可以连结形成3~6元环。作为形成3~6元环的基团,可以列举出环丙烷-1,1-二基、环丁烷-1,1-二基、2,4-二甲基环丁烷-1,1-二基、3-二甲基环丁烷-1,1-二基、环戊烷-1,1-二基、环己烷-1,1-二基、四氢吡喃-4,4-二基、噻蒽(thiane)-4,4-二基、哌啶-4,4-二基、N-取代哌啶-4,4-二基、吗啉-2,2-二基、吗啉-3,3-二基、N-取代吗啉-2,2-二基,N-取代吗啉-3,3-二基等;作为该N-取代基,可以列举出作为环A和环B的取代基所例示的那些基团。
当上述通式(I)的Y1和Y2不为上述通式(IV)所示的基团时,则为氢原子或碳原子数为1~30的有机基团,如果作为取代基的该有机基团较大,则有可能花青化合物的摩尔吸光系数变小,影响感度,所以作为Y1和Y2所示的碳原子数为1~30的有机基团,优选碳原子数为1~8的烃基,更优选碳原子数为1~8的烷基。从同样的观点出发,X为NY时,Y所表示的碳原子数为1~30的有机基团也优选碳原子数为1~8的烃基,更优选碳原子数为1~8的烷基。
上述通式(I)中,作为由Z表示的卤原子可以列举出氟、氯、溴、碘等。
本发明的花青化合物中,上述通式(I)中的X为CR3R4的化合物具有适合于光学记录材料的吸收波长,因而优选,所述光学记录材料在采用550~620nm的半导体激光的光学记录介质的光学记录层中使用。
在上述通式(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)膦酸阴离子等有机磷酸系阴离子等;作为二价阴离子,可以列举出例如苯二磺酸阴离子、萘二磺酸阴离子等。另外,必要时也可使用具有使处于激发态的活性分子去激发(猝灭)功能的金属络合物系猝灭剂阴离子、以及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、二茂钌等茂金属化合物阴离子等。
作为上述金属络合物系猝灭剂阴离子,可以列举出例如偶氮螯合络合物、由下述通式(A)或(B)表示的化合物、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。
(式中,M’表示镍原子或铜原子,R18和R19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、可由卤原子取代的芳基、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,R20、R21、R22和R23各自独立地表示烷基、烷基苯基、烷氧基苯基或卤代苯基。)
上述通式(I)中,Anm-表示的阴离子为高氯酸阴离子的花青化合物分解时放出大量的热。此外,该阴离子为高氯酸阴离子的花青化合物具有分解温度特别低的特点,有时由于凹坑的热干扰而使跳动性能变差。因此,本发明的花青化合物用于光学记录材料时,优选该阴离子为高氯酸阴离子以外的阴离子的花青化合物。
上述通式(II)中,作为R5~R8所示的卤原子,可以列举出氟、氯、溴、碘等;作为R5~R8所示的可被卤原子取代的碳原子数为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、氯甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、全氟乙基、全氟丙基、全氟丁基等;作为R5所示的可被卤原子取代的碳原子数为1~4的烷氧基,可以列举出甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基等,作为R6和R8结合形成的环结构,可以列举出环丁烯环、环戊烯环、环己烯环、吡咯环、二氢吡咯环、吡啶环等。
上述通式(III)中,作为含有E’和G’并且可以含有杂原子的5元环,可以列举出环戊烯环、环戊二烯环、吡咯环、咪唑环、吡唑环、三唑环、噻吩、呋喃环、噻唑环、异噻唑环、噁唑环、异噁唑环、二氢吡咯环、二氢咪唑环、二氢吡唑环、二氢噻吩环、二氢呋喃环、二氢噻唑环、二氢异噻唑环、二氢噁唑环、二氢异噁唑环等,作为含有E’和G’并且含有杂原子的6元环,可以列举出吡啶环、吡嗪环、嘧啶环、哒嗪环、吡喃环、噻喃环等。此外,上述含有E’和G’的环还可以被氟、氯、溴、碘等卤原子;硝基;氰基;甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、三氟甲基等烷基;甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基等烷氧基取代。
上述通式(IV)中,作为R9~R17所示的碳原子数为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。作为被卤原子取代的上述烷基,可以列举出氯甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、全氟乙基、全氟丙基、全氟丁基等,作为上述烷基的链中的亚甲基被-O-取代的基团,可以列举出甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基、2-甲氧基乙氧基、2-甲氧基乙基、氯甲氧基、二氯甲氧基、三氯甲氧基、溴甲氧基、二溴甲氧基、三溴甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、全氟乙氧基、全氟丙氧基、全氟丁氧基等,作为上述烷基的链中的亚甲基被-CO-取代的基团,可以列举出乙酰基、丙酰基、一氯乙酰基、二氯乙酰基、三氯乙酰基、三氟乙酰基、丙烷-2-酮-1-基、丁烷-2-酮-1-基等。
上述通式(IV)中,作为J所示的碳原子数为1~8的亚烷基,可以列举出亚甲基、亚乙基、亚丙基、甲基亚乙基、亚丁基、1-甲基亚丙基、2-甲基亚丙基、1,2-二甲基亚丙基、1,3-二甲基亚丙基、1-甲基亚丁基、2-甲基亚丁基、3-甲基亚丁基、4-甲基亚丁基、2,4-二甲基亚丁基、1,3-二甲基亚丁基、亚戊基、亚己基、亚庚基、亚辛基、乙烷-1,1-二基、丙烷-2,2-二基、环丙烷-1,1-二基、环丙烷-1,2-二基、环丁烷-1,1-二基、环丁烷-1,2-二基、环戊烷-1,1-二基、环戊烷-1,2-二基、环戊烷-1,3-二基、环己烷-1,1-二基、环己烷-1,2-二基、环己烷-1,3-二基、环己烷-1,4-二基、甲基环己烷-1,4-二基等。此外,上述亚烷基中的亚甲基被-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-取代时,其取代的位置和数量是任意的。
上述通式(IV)所示的基团中,具有M为Fe、J为碳原子数为1~8的亚烷基的基团的本发明的花青化合物因生产成本低廉且耐光性优良,所以优选。
作为上述通式(I)所示的本发明的花青化合物的优选具体例子,可以列举出下述化合物No.1~45。另外,在以下例子中,以省略了阴离子的花青化合物阳离子表示。
Figure GSB00000131496800091
Figure GSB00000131496800111
Figure GSB00000131496800121
上述本发明的上述通式(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-甲基吲哚季盐衍生物与N,N’-二苯基甲脒等桥联剂反应得到。另外,上述通式(II)或(III)所示的具有多重键的基团可以在得到作为中间体的2-甲基吲哚季盐衍生物的过程中引入。作为其方法,可以列举出例如,以芳基肼衍生物作为起始物质,在利用具有前述通式(II)或(III)所示的多重键基团的2-丁酮衍生物形成吲哚环时引入的方法;使吲哚环与卤代衍生物反应而引入的方法。Y、Y1和Y2可分别通过与芳基胺衍生物或吲哚环的NH反应的Y-D、Y1-D和Y2-D(D是氯、溴、碘等卤素基;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,具有前述通式(II)或(III)所示的多重键基团的2-丁酮衍生物可以通过使丙酮与具有相应取代基的苯甲醛反应而制得。
此外,作为引入前述通式(IV)所示的基团的方法,可以列举出例如前述专利文献1所记载的方法。
本发明的光学记录材料用于形成在基体上形成了光学记录层的薄膜的光学记录介质的该光学记录层,包括前述通式(I)所示的本发明的花青化合物本身以及该花青化合物与后述的有机溶剂和/或各种化合物的混合物。
关于使用本发明的光学记录材料形成光学记录介质的光学记录层的方法,没有特别的限制。通常,可使用通过旋涂、喷涂、浸渍等在基体上涂布在如下的有机溶剂中溶解有本发明的花青化合物以及根据需要溶解有后述的各种化合物的溶液的湿式涂布法,上述有机溶剂为: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、乙酸丁酯、乙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;2,2,2-三氟乙醇、全氟乙醇、2,2,3,3-四氟-1-丙醇、全氟丙醇等氟代醇类;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,可以例举出蒸镀法、溅射法等。
上述光学记录层的厚度通常适宜的范围是0.001~10μ,优选范围为0.01~5μ。
此外,当使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,该光学记录层中上述通式(I)所示的本发明的花青化合物的含量优选为25~100质量%。要形成上述花青化合物含量的光学记录层,在本发明的光学记录材料中,以本发明的光学记录材料中所含的固体成分为基准,优选含有25~100质量%的本发明的花青化合物。
另外,上述光学记录层中除了含有上述通式(I)所示的本发明的花青化合物之外,必要时还可以含有其它的花青系化合物、偶氮系化合物、酞菁系化合物、氧杂菁(oxonol)系化合物、方酸内鎓盐(squarylium)系化合物、苯乙烯基系化合物、卟吩系化合物、偶氮金属络合物等可用于光学记录层的着色剂化合物;聚乙烯、聚酯、聚苯乙烯、聚碳酸酯等树脂类,还可以含有表面活性剂;抗静电剂;润滑剂;阻燃剂;受阻胺等自由基捕捉剂;二茂铁衍生物等凹坑形成促进剂;分散剂;抗氧化剂;交联剂;耐光性赋予剂等。另外,上述光学记录层可以含有作为单态氧等的猝灭剂的芳香族亚硝基化合物、胺鎓化合物、亚胺鎓化合物、双亚胺鎓化合物、过渡金属螯合物等。
上述各种化合物优选以0~75质量%的范围用于上述光学记录层中。因此,在本发明的光学记录材料中,以本发明的光学记录材料所含的固体成分为基准,上述各种化合物的含量优选为0~75质量%。
设置上述光学记录层的上述基体的材料只要是对写入(记录)光和读取(再生)光实质上是透明的即可,没有特别的限制,例如,可以使用聚甲基丙烯酸甲酯、聚对苯二甲酸乙二醇酯、聚碳酸酯等树脂、玻璃等。另外,根据用途,其形状可以使用卷尺状、圆筒状、带状、圆盘状等任意形状。
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,也可利用丙烯酸树脂、紫外线固化性树脂等形成保护层。
本发明的光学记录材料适用于在记录和再生中使用半导体激光的光学记录介质,特别适用于高速记录型的DVD-R等光盘。
此外,本发明的花青化合物除了可以用于光学记录材料以外,也可以用于液晶显示器和等离子体显示器等图像显示设备的滤光器用光吸收材料。
实施例
下面,通过实施例等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.4的六氟化磷盐的制造
按照下述合成路线和合成步骤,以72%的收率得到化合物No.4的六氟化磷盐。
合成路线
Figure GSB00000131496800151
(合成步骤)
在反应烧瓶中加入0.003摩尔上述合成路线中所示的(A)、0.06摩尔(D)和0.0042摩尔(C)并搅拌。向其中加入0.003摩尔(B),在45℃下搅拌2.5小时后,加入0.0045摩尔(E)和10g甲醇,在55℃下搅拌1小时。静置12小时后,过滤得到晶体,用甲醇和水洗涤后,在180℃下真空干燥35小时。
对干燥后的晶体进行分析,证实该晶体为作为目标物的化合物No.4的六氟化磷盐。分析结果如下所示。
·光学特性(氯仿,3.60×10-6摩尔/升)
λmax;596nm,ε;1.26×105
·分子量(TOF-质谱分析)
904.8
·熔点(100ml/分钟的氮气流下在10℃/分钟的升温条件下的示差热分析DTA的吸收峰顶点)
226.5℃
·1H-NMR(溶剂:DMSO)
图1表示1H-NMR谱图。
[评价例]
对上述实施例1得到的化合物No.4的六氟化磷盐和以下所示的比较化合物1~3进行示差热分析,测定热分解温度和分解产生的放热。另外,热分解温度定为在氮气中以10℃/分钟的升温条件得到的DTA的发热最高峰温度。结果示于表1中。
Figure GSB00000131496800161
表1
Figure GSB00000131496800162
根据上述表1的结果可以证实,本发明的花青化合物与类似的花青化合物相比,可以在较低温度下分解。这表示本发明的花青化合物具有适合光学记录材料的热分解行为。
根据本发明,可以提供其分解行为适合光学记录材料的花青化合物、以及含有该花青化合物的光学记录材料,所述光学记录材料用于可实现高速记录的光学记录介质的光学记录层中。

Claims (5)

1.下述通式(I)所示的花青化合物,
Figure FSB00000079017400011
式中,环A和环B表示可以具有取代基的苯环或萘环,X表示CR3R4,R1和R2中的至少一个表示下述通式(II)或(III)所示的基团,当仅有一个是下述通式(II)或(III)所示的基团时,另一个表示碳原子数为1~30的烷基,R3和R4表示碳原子数为1~30的烷基或碳原子数为1~30的芳烷基、或者R3和R4连结形成3~6元环的基团,Y1和Y2中的至少一个表示下述通式(IV)所示的基团,当仅有一个是下述通式(IV)所示的基团时,另一个表示选自氢原子、碳原子数为1~30的烷基、碳原子数为1~30的芳烷基中的一种,Z表示氢原子、卤原子或氰基,Anm-表示m价的阴离子,m表示1或2的整数,p表示保持电荷为中性的系数,
其中,所述取代基选自下述基团中的一种:选自于氟、氯、溴、碘之中的卤素基;选自于甲基、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、三氟甲基之中的基团;选自于甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基之中的基团;选自于甲硫基、乙硫基、丙硫基、异丙硫基、丁硫基、仲丁硫基、叔丁硫基之中的烷基硫基;硝基;和氰基;
Figure FSB00000079017400012
通式(II)中,E和G之间的键是双键或三键,E表示碳原子,G表示碳原子、氧原子或氮原子,x、y和z表示0或1,R5表示氢原子、卤原子、可被卤原子取代的碳原子数为1~4的烷基或可被卤原子取代的碳原子数为1~4的烷氧基,R6、R7和R8分别独立地表示氢原子、卤原子或可被卤原子取代的碳原子数为1~4的烷基,R6和R8可以结合形成环结构;通式(III)中,E’和G’之间的键是双键,E’表示碳原子,G’表示碳原子,含E’和G’的环表示苯环或萘环,所述含E’和G’的环可被羟基、卤原子、硝基、氰基、烷基、烷氧基、三氟甲基、三氟甲氧基取代,所述烷基选自甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基中的一种,所述烷氧基选自甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基中的一种;通式(IV)中,R9~R17表示氢原子或可被卤原子取代且链中的亚甲基可被-O-或-CO-取代的碳原子数为1~4的烷基,M表示Fe、Co、Ni、Ti、Cu、Zn、Zr、Cr、Mo、Os、Mn、Ru、Sn、Pd、Rh或Pt,J表示直接键合或碳原子数为1~8的亚烷基,所述亚烷基中的亚甲基可以被-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-取代。
2.根据权利要求1记载的花青化合物,其中,所述通式(I)中,Anm-是高氯酸阴离子以外的阴离子。
3.根据权利要求1或2记载的花青化合物,其中,所述通式(I)中,R1和R2中的至少一个是可被羟基、卤原子、硝基、氰基、碳原子数为1~4的烷基或碳原子数为1~4的烷氧基取代的苄基。
4.根据权利要求1或2记载的花青化合物,其中,所述通式(IV)中,M是Fe,J是碳原子数为1~8的亚烷基。
5.一种光学记录材料,其用于在基体上形成有光学记录层的光学记录介质的该光学记录层中,其中,含有权利要求1~4中任一项记载的花青化合物。
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