CN1513172A - 在信息层中包含作为吸光化合物的二氮杂半花青染料的光学数据存储介质 - Google Patents
在信息层中包含作为吸光化合物的二氮杂半花青染料的光学数据存储介质 Download PDFInfo
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- CN1513172A CN1513172A CNA028108884A CN02810888A CN1513172A CN 1513172 A CN1513172 A CN 1513172A CN A028108884 A CNA028108884 A CN A028108884A CN 02810888 A CN02810888 A CN 02810888A CN 1513172 A CN1513172 A CN 1513172A
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- ethyl
- represent
- cyanogen
- methyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- 238000013500 data storage Methods 0.000 title claims description 11
- 230000003287 optical effect Effects 0.000 claims abstract description 37
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims abstract 4
- -1 pyrazole-3-yl Chemical group 0.000 claims description 110
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 72
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 21
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 20
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 20
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 20
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
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- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 6
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- 239000011630 iodine Substances 0.000 claims description 6
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- 238000010521 absorption reaction Methods 0.000 claims description 5
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 4
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 4
- 241001062009 Indigofera Species 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 240000000233 Melia azedarach Species 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- NSHIYIMHYBAIEY-UHFFFAOYSA-N ethyl hypochlorite Chemical compound CCOCl NSHIYIMHYBAIEY-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005842 heteroatom Chemical group 0.000 claims description 2
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- ABSXMLODUTXQDJ-UHFFFAOYSA-N 4-(4-sulfophenyl)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=C(S(O)(=O)=O)C=C1 ABSXMLODUTXQDJ-UHFFFAOYSA-N 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
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Abstract
包含优选透明的基体的光学数据存储介质,其已经任选被一个或多个反射层涂覆并且在其表面涂覆有光可记录的信息层,任选一个或多个反射层和任选保护层或另外的基体或上层,该数据存储介质可以使用蓝或红光,优选激光记录和读取,其中信息层包含吸光化合物和任选粘合剂,特征在于至少一种二氮杂半花青染料被用作吸光化合物。
Description
本发明涉及在信息层中包含作为吸光化合物的二氮杂半花青(hemicyanine)染料的优选一次性可记录的光学数据存储介质,和其生产方法。
使用特殊的吸光物质或其混合物的可记录光学数据存储介质特别适合应用于高密度可记录光学数据存储介质,该介质用蓝激光二极管操作,特别是GaN或SHG激光二极管(360-460nm),和/或用于DVD-R或CD-R光盘,该光盘用红(635-660nm)或红外(780-830nm)激光二极管操作,和以上提到的染料对于通过旋转涂覆或蒸汽淀积的聚合物基体,特别是聚碳酸酯的应用。
最近可记录光盘(CD-R,780nm)的销售有大量的增长,这代表技术上确立的***。
下一代光学数据存储介质-DVD-目前正被引入市场。通过使用短波激光照射(635-660nm)和较高的数值孔径NA,可以增加存储密度。在这种情况下可记录格式是DVD-R。
现在,使用具有高激光功率的蓝激光二极管(以GaN为基础,JP 08191 171或
Second
Harmonic
Generation SHG JP 09 050 629)(360-460nm)的光学数据存储格式正在形成。因此可记录光学数据存储介质也被用于这一代。可获得的存储密度取决于激光斑点在信息平面内的聚焦。斑大小与激光波长λ/NA成比例。NA是使用物镜的数值孔径。目的是使用尽可能小的可能的波长λ以取得尽可能高可能的存储密度。以半导体激光二极管为基础,目前390nm是可能的。
专利文献描述了同样适用于CD-R和DVD-R***的以染料为基础的可记录光学数据存储介质(JP-A 11 043 481和JP-A 10 181 206)。在记录的过程中为了获得高反射性和读出信号的高调制水平和足够的敏感性,CD-R的IR波长780nm被定位在染料吸收峰的长波斜坡(slope)基部上和DVD-R的红光波长635nm或650nm被定位在染料吸收峰的短波斜坡基部上。在JP-A 02 557 335,JP-A 10 058 828,JP-A 06 336086,JP-A 02 865 955,WO-A 09 917 284和US-A 5 266 699中这个概念被延伸覆盖吸收峰在短波长斜度的450nm的工作波长范围和在长波长斜度的红光和IR范围。
除了以上提到的光学性能,由吸光有机物质组成的可记录信息层必须具有尽可能无定形的形态,以便在记录或读取过程中的噪音信号尽可能小。为此目的,当通过由溶液的旋转涂覆或通过汽相淀积和/或升华涂覆该物质时,特别优选在随后的在真空中使用金属或介电层的表面涂饰的过程中防止吸光物质的结晶。
吸光物质的无定形层应优选具有高的热稳定性,因为否则通过喷镀或蒸汽淀积涂覆到吸光信息层上的另外的有机或无机物质层由于扩散形成模糊边界,并因此对反射性产生不利影响。另外,如果吸光物质在边界对于聚合基体不具有足够的热稳定性,它可以扩散入聚合基体并又会对反射性产生不利影响。
如果吸光物质具有太高的蒸汽压力,在高真空中在以上提到的另外层的喷镀或蒸汽淀积过程中,它可以升华并因此减少了所需涂层厚度。这反过来对反射性具有消极影响。
因此本发明的目的是提供合适的化合物,其满足了用于可记录光学数据存储体的信息层的高要求(例如光稳定性,有利的信号/噪音比率,无损害的涂覆到基体材料上等),特别是在340-680nm的激光波长范围内用于高密度可记录光学数据存储格式。
令人惊讶地是,已经发现由二氮杂半花青类染料形成的吸光化合物特别适合于满足以上提到的要求。
因此本发明涉及包含优选透明基体的光学数据存储介质,其任选已经用一个或多个反射层涂覆并且在其表面涂覆光可记录信息层,任选一个或多个反射层和任选保护层或另外基体或上层,该光学数据存储介质可以使用蓝或红光,优选激光,记录和读取,其中信息层包含吸光化合物和任选粘合剂,特征在于至少一种二氮杂半花青染料被用作吸光化合物。
特别优选蓝激光。
吸光化合物应优选可热改性的。热改性优选在<600℃的温度下进行,特别优选在<400℃的温度下,非常特别优选在<300℃的温度下,和特别在<200℃的温度下进行。例如,这样的改性可以是吸光化合物的发色中心的分解或化学改性。
优选具有下式(I)的二氮杂半花青,
其中K代表具有下式(II)到(IV)的基团,
X1代表O或S,
X2代表O,S,CH或N-R2,
X3代表N,CH或C-CN,
R1,R1和R12彼此独立地代表C1-到C16-烷基,C3-到C6-链烯基,C5-到C7-环烷基或C7-到C16-芳烷基,
A与X2和其中连接的碳原子一起代表可以包含1-4个杂原子和/或可以被苯并或萘并稠合和/或被非离子基团取代的五元芳族或准芳族杂环,
R3,R4,R5和R6彼此独立地代表氢,C1-到C16-烷基,C4-到C7-环烷基,C7-到C16-芳烷基或杂环基团或
NR3R4或NR5R6彼此独立地代表通过氮相连并可以另外包含N或O原子和/或被非离子基团取代的五元或六元饱和环,
R7代表氢,C1-到C16-烷基,C1-到C16-烷氧基或卤素或
R7和R5形成可以包含O或N原子和/或被非离子基团取代的二元或三元桥,
R8代表氢,C1-到C16-烷基,C1-到C16-烷氧基,卤素,氰基,C1-到C4-烷氧羰基,O-CO-R10,NH-CO-R10,O-SO2-R10或NH-SO2-R10,
R9代表氢,C1-到C4-烷基或C6-到C10-芳基,
R10代表氢,C1-到C16-烷基,C4-到C7-环烷基,C7-到C16-芳烷基,C1-到C16-烷氧基,单-或双-C1-到C16-烷基胺基,C6-到C10-芳基,C6-到C10-芳氧基,C6-到C10-芳胺基或杂环基团,
R11代表氢,C1-到C4-烷基或C6-到C10-芳基和
An代表阴离子。
合适的非离子基团是,例如,C1-到C4-烷基,C1-到C4-烷氧基,卤素,氰基,硝基,C1-到C4-烷氧羰基,C1-到C4-烷硫基,C1-到C4-烷酰基胺基,苯甲酰胺基,单-或双-C1-到C4-烷基胺基。
烷基,烷氧基,芳基和杂环基团可以任选包含另外的基团,例如烷基,卤素,硝基,氰基,CO-NH2,烷氧基,三烷基甲硅烷基,三烷基甲硅烷氧基或苯基,烷基和烷氧基基团可以是直链的或支链的,烷基基团可以被部分卤代或全卤代,烷基和烷氧基基团可以被乙氧基化或丙氧基化或甲硅烷基化,在芳基或杂环基团上的相邻的烷基和/或烷氧基基团可以一起形成三或四元桥并且杂环基团可以被苯并稠合和/或季铵化(quaternized)。
具有下式的环A
特别优选代表噻唑-2-基,苯并噻唑-2-基,苯并噁唑-2-基,苯咪唑-2-基,咪唑-2-基,吡唑-3-基,1,3,4-***-2-基,1,3,4-噻二唑-2-基,1,2,4-噻二唑-5-基,2-或4-吡啶基或2-或4-喹啉基,其中以上提到的环每一个可以通过以下取代:C1-到C6-烷基,C1-到C6-烷氧基,氟,氯,溴,碘,氰基,硝基,C1-到C6-烷氧羰基,C1-到C6-烷硫基,C1-到C6-酰胺基,C6-到C10-芳基,C6-到C10-芳氧基,C6-到C10-芳基羰基胺基,单-或双-C1-到C6-烷基胺基,N-C1-到C6-烷基-N-C6-到C10-芳基胺基,吡咯子基(pyrrolidino),吗啉代(morpholino)或哌嗪子基(piperazino)。
在特别优选的形式中使用的二氮杂半花青是具有式(I)的那些,
其中
具有下式的环A
代表噻唑-2-基,苯并噻唑-2-基,其中X2代表S并且以上提到的基团每一个可以通过甲基,乙基,甲氧基,乙氧基,氯,氰基,甲氧羰基或乙氧羰基取代,或代表1,3,4-***基或1,3,4-噻二唑基,其中X2代表N-R2或S,并且以上提到的基团每一个可以通过以下取代:甲基,乙基,苯基,甲氧基,乙氧基,甲硫基,乙硫基,氨基,苯胺基,二甲基胺基,二乙基胺基,二丙基胺基,二丁基胺基,N-甲基-N-氰代乙基胺基,N-甲基-N-羟基乙基胺基,N-甲基-N-苯基胺基,双-(氰代乙基)胺基,双-(羟基乙基)胺基,氰代乙基胺基,羟基乙基胺基,吡咯子基,哌啶子基,吗啉代或具有下式的基团,
K代表具有式(II),(III)或(IV)的基团,
X1代表O或S,
X3代表N,CH或C-CN,
R1,R2和R12彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,苯乙基,苯基丙基,烯丙基,环己基,氯乙基,氰代甲基,氰代乙基,氰代丙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,
R3,R4,R5和R6彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,苯乙基,苯基丙基,环己基,氯乙基,氰代甲基,氰代乙基,氰代丙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基,乙酸基乙基,丙酸基乙基或具有下式的基团
并且R3和R5可以另外代表氢或
NR3R4和NR5R6彼此独立地代表吡咯子基,哌啶子基,N-甲基哌嗪子基,N-乙基哌嗪子基,N-羟基乙基哌嗪子基或吗啉代,
R7代表氢,甲基,甲氧基或氯或
R7;R5代表-(CH2)2,-(CH2)3-,-C(CH3)-CH2-C(CH3)2-或-O-(CH2)2-桥,
R8代表氢,甲基,甲氧基或氯,
R9代表氢,
R11代表氢,甲基或苯基和
An代表阴离子。
合适的阴离子An全部是单价阴离子或一当量的多价阴离子。优选无色阴离子。合适的阴离子,例如,氯离子,溴离子,碘离子,四氟硼酸根,高氯酸根,六氟硅酸根,六氟磷酸根,甲硫酸根,乙硫酸根,C1-到C10-烷基磺酸根,C1-到C10-全氟烷基磺酸根,任选通过氯,羟基或C1-到C4-烷氧基取代的C1-到C10-链烷酸根,任选通过硝基,氰基,羟基,C1-到C25-烷基,全氟-C1-到C4-烷基,C1-到C4-烷氧羰基或氯取代的苯磺酸根,萘磺酸根或联苯磺酸根,任选通过硝基,氰基,羟基,C1-到C4-烷基,C1-到C4-烷氧基,C1-到C4-烷氧基羰基或氯取代的苯二磺酸根,萘二磺酸根或联苯二磺酸根,任选通过硝基,氰基,C1-到C4-烷基,C1-到C4-烷氧基,C1-到C4-烷氧羰基,苯甲酰基,氯苯甲酰基或甲苯酰基取代的苯甲酸根,下列的阴离子:萘二羧酸或联苯二磺酸根,四苯基硼酸根,氰代三苯基硼酸根,四-C1-到C20-烷氧基硼酸根,四-C1-到C4-苯氧基硼酸根,任选在B-和/或C-原子通过一个或两个C1-到C12-烷基或苯基基团取代的7,8-或7,9-联咔(dicarba)-巢状(nido)-十一硼酸根(1-)或(2-),十二氢-联咔十二烷基硼酸根(2-)或B-C1-到C12-烷基-C-苯基-十二氢-联咔十二烷基硼酸盐(1-)。
优选溴离子,碘离子,四氟硼酸根,高氯酸根,甲磺酸根,苯磺酸根,甲苯磺酸根,十二烷基苯磺酸根,十四烷基磺酸根。
在特别优选的形式中使用的二氮杂半花青是具有下式(VI)到(IX)的那些,
其中
R1和R2彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代甲基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基或具有下式的基团,
R5和R6彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基或乙酸基乙基或
NR5R6代表吡咯子基,哌啶子基或吗啉代,
R7代表氢或
R7;R5代表-(CH2)2-,-C(CH3)-CH2-C(CH3)2-,或-O-(CH2)2-桥,
R8代表氢,
R13,R14和R15彼此独立地代表氢,甲基,甲氧基,氯,硝基或氰基,
R16和R17彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基,乙酸基乙基或苯基和
R16另外代表氢或
NR16R17代表吡咯子基,哌啶子基或吗啉代,和
An代表四氟硼酸根,高氯酸根,六氟硅酸根,六氟磷酸根,碘阴离子,硫氰酸根,氰酸根,羟基乙酸根,甲氧基乙酸根,乳酸根,柠檬酸根,甲磺酸根,乙磺酸根,苯磺酸根,甲苯磺酸根,丁基苯磺酸根,氯苯磺酸根,十二烷基苯磺酸根或萘磺酸根,
其中所有的烷基基团可以是支链的。
在特别优选形式中使用的二氮杂半花青是具有下式(X)到(XIII)的那些,
其中
R1和R2彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代甲基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基或具有下式的基团,
X1代表O和
X3代表CH或
X1代表S和
X3代表N,CH或C-CN,
R3和R4彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基或乙酸基乙基或
NR3R4代表吡咯子基,哌啶子基或吗啉代,
R9代表氢,
R13,R14和R15彼此独立地代表氢,甲基,甲氧基,氯,硝基或氰基,
R16和R17彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基,乙酸基乙基或苯基和
R16另外代表氢或
NR16R17代表吡咯子基,哌啶子基或吗啉代,和
An-代表四氟硼酸根,高氯酸根,六氟硅酸根,六氟磷酸根,碘阴离子,硫氰酸根,氰酸根,羟基乙酸根,甲氧基乙酸根,乳酸根,柠檬酸根,甲磺酸根,乙磺酸根,苯磺酸根,甲苯磺酸根,丁基苯磺酸根,氯苯磺酸根,十二烷基苯磺酸根或萘磺酸根,
其中所有的烷基基团可以是支链的。
在特别优选形式中使用的二氮杂半花青是具有下式(XIV)到(XVII)的那些,
其中
R1,R2和R12彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代甲基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基或具有下式的基团,
R13,R14和R15彼此独立地代表氢,甲基,甲氧基,氯,硝基或氰基,
R16和R17彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基,乙酸基乙基或苯基和
R16另外代表氢或
NR16R17代表吡咯子基,哌啶子基或吗啉代,
R11代表氢,甲基或苯基和
An-代表四氟硼酸根,高氯酸根,六氟硅酸根,六氟磷酸根,碘阴离子,硫氰酸根,氰酸根,羟基乙酸根,甲氧基乙酸根,乳酸根,柠檬酸根,甲磺酸根,乙磺酸根,苯磺酸根,甲苯磺酸根,丁基苯磺酸根,氯苯磺酸根,十二烷基苯磺酸根或萘磺酸根,
其中所有的烷基基团可以是支链的。
在特别优选形式中使用的二氮杂半花青是具有式(IX),(XIII)和(XVII)的那些。
对于根据本发明的使用蓝激光的光记录和读取的可记录光学数据存储介质,这样的二氮杂半花青染料是优选的,其吸收最大值λmax2在420-550nm范围内,其中,在波长λmax2吸收最大值的短波斜坡处的消光是在λmax2的消光值的一半的波长λ1/2和在波长λmax2吸收最大值的短波斜坡处的消光是在λmax2的消光值的十分之一的波长λ1/10,在每一种情况下优选彼此相差不超过50nm。优选这样的二氮杂半花青染料在波长350nm以下,特别优选320nm以下,和非常特别优选290nm以下没有显示短波最大值λmax1。
优选的二氮杂半花青染料是具有410-530nm吸收最大值λmax2的那些。
特别优选的二氮杂半花青染料是具有420-510nm吸收最大值λmax2的那些。
非常特别优选的二氮杂半花青染料是具有430-500nm吸收最大值λmax2的那些。
在这些二氮杂半花青染料中λ1/2和λ1/10,如以上所定义,优选彼此相差不超过40nm,特别优选不超过30nm,和非常特别优选不超过20nm。
对于根据本发明的使用红激光的光记录和读取的可记录光学数据存储介质,这样的二氮杂半花青染料是优选的,其吸收最大值λmax2在500-650nm范围内,其中,在波长λmax2吸收最大值的长波斜坡处的消光是在λmax2的消光值的一半的波长λ1/2,和在波长λmax2吸收最大值的长波斜坡处的消光是在λmax2的消光值的十分之一的波长λ1/10,在每一种情况下优选彼此相差不超过50nm。优选这样的二氮杂半花青染料在波长750nm以下,特别优选800nm以下,和非常特别优选850nm以下没有显示长波最大值λmax3。
优选的二氮杂半花青染料是具有530-630nm吸收最大值λmax2的那些。
特别优选的二氮杂半花青染料是具有550-620nm吸收最大值λmax2的那些。
非常特别优选的二氮杂半花青染料是具有580-610nm吸收最大值λmax2的那些。
在这些二氮杂半花青染料中λ1/2和λ1/10,如以上所定义,优选彼此相差不超过40nm,特别优选不超过30nm,和非常特别优选不超过20nm。
在吸收最大值λmax2二氮杂半花青染料具有>30000l/mol cm,优选>40000l/mol cm,特别优选>50000l/mol cm和非常特别优选>70000l/mol cm的摩尔消光系数ε。
吸收光谱,例如,在溶液中测量。
具有要求的光谱性能的合适的二氮杂半花青是那些其中在偶极矩变化Δμ=|μg-μag|,即在基态和第一激发态偶极矩之间的正差尽可能小的,即优选<5D,和特别优选<2D。例如,在F.Würthner等人,Angew.Chem.1997,109,2933,和其中引用的文献中描述了测定这种偶极矩改变Δμ的方法。低溶剂化显色(solvatochromism)(甲醇/二氯甲烷)也是合适的选择标准。优选的二氮杂半花青染料是那些其溶剂化显色Δλ=|λ二氯甲烷-λ甲醇|,即在溶剂二氯甲烷和甲醇中的吸收波长间的正差是<25nm,特别优选<15nm,和非常特别优选<5nm。
具有式(I)和(VI)到(XVII)的二氮杂半花青是已知的,例如,由BE 825 455,DE-OS 1 044 023,DE-OS 2 811 258,DE-OS 1 163775。
本发明的另一部分是具有式(I)的二氮杂半花青,其中K表示具有式(III)的基团并且其它的基团具有上面的意思。本发明的另一特殊部分是具有式(X),(XI),(XII)或(XIII)的二氮杂半花青,其中基团具有上面的意思。
描述的吸光物质保证了在未记录状态下的光学数据存储介质的足够高的反射性(>10%)和使用会聚光逐点照射的信息层的热降解的足够高的吸收,如果光的波长在360-460nm和600-680nm的范围的话。作为随后的热降解的信息层改变的光学性能的结果,通过就入射光的振幅以及相位而言的反射性的变化,进行在光学数据存储介质记录和未记录区的对比。
二氮杂半花青染料优选通过旋转涂覆或真空涂覆涂覆到光学数据存储介质上。二氮杂半花青可以与其它的二氮杂半花青或与其它的具有相似光谱性能的染料混合。除了二氮杂半花青染料信息层可以包含添加剂,例如粘合剂,湿润剂,稳定剂,稀释剂和敏化剂以及其它组分。
除了信息层,光学数据存储介质可以包含其它的层,例如金属层,介电层和保护层。例如,金属和介电层用于调整反射性和热平衡性。金属可以是金,银或铝等,这取决于激光波长。例如,介电层是二氧化硅和四氮化三硅。例如,保护层是可光致固化的表面涂层,粘合层和保护膜。
粘合剂层可以由压敏材料组成。
压力敏感粘合层主要由丙烯酸粘合剂组成。例如,Nitto DenkoDA-8320或DA-8310,其公开在专利JP-A 11-273147中,可以被用于此目的。
光学数据存储介质具有,例如,以下层组合(参见图1):透明基体(1),任选保护层(2),信息层(3),任选保护层(4),任选粘合剂层(5)和上层(6)。
光学数据存储介质组合可以优选包含:
-优选透明的基体(1),在其表面涂覆有至少一种可光致固化的信息层(3),该信息层可以使用光记录,优选激光,任选保护层(4),任选粘合层(5)和透明上层(6);
-优选透明的基体(1),在其表面涂覆有保护层(2),至少一种信息层(3),该信息层可以使用光记录,优选激光,任选粘合层(5)和透明上层(6);
-优选透明的基体(1),在其表面涂覆有任选保护层(2),至少一种信息层(3),该信息层可以使用光记录,优选激光,任选保护层(4),任选粘合层(5)和透明上层(6);
-优选透明的基体(1),在其表面涂覆有至少一种信息层(3),该信息层可以使用光记录,优选激光,任选粘合层(5)和透明上层(6)。
另外,光学数据存储介质具有,例如,下面的层组合(参见图2):优选透明基体(11),信息层(12),任选反射层(13),任选粘合层(14)和另外的,优选透明基体(15)。
本发明也涉及根据本发明的光学数据存储介质,其可以使用蓝或红光记录,特别是激光。
下面的实施例说明本发明。
实施例
实施例1
4g 2-氨基-5-(二异丙基胺基)-1,3,4-噻二唑被溶解于40ml冰醋酸中。8ml 85重量%的磷酸和6ml 48重量%的硫酸在10℃下被逐滴添加。之后6.8g亚硝基硫酸(在硫酸中40重量%)在5℃下在30分钟的时间里被逐滴添加。4小时后在0-5℃下过量亚硝基盐用氨基磺酸破坏。
这种重氮化的产品在10℃下在1小时的时间里被逐滴添加到5g 2-吗啉代-4-苯基噻唑在30ml冰醋酸的溶液中,用20重量%的苏打水溶液维持pH为3。在pH为3.5的条件下搅拌过夜后混合物被抽滤残渣被用水洗涤。固体在100ml的水中搅拌混合物被调整到pH为7.5,再一次抽滤残渣被用水洗涤。干燥后,粗制品被溶解于100ml的甲苯中。通过在搅拌下慢慢加入400ml己烷,产品被沉淀,抽滤,用己烷洗涤之后用水洗涤和干燥。获得了3.7g(理论的41%)具有下式的紫色粉末。
M.p.=155℃
λmax(二噁烷)=531nm。
2.3g以上的偶氮染料被溶解于20ml冰醋酸中。添加1.3硫酸二甲酯混合物在70℃下被搅拌5小时。冷却至室温后添加200ml水。溶液用50ml甲苯之后用100ml氯仿提纯。氯仿相被蒸发至干燥。产生的紫色染料被溶解于30ml甲醇中。添加0.6g高氯酸锂。搅拌过夜后沉淀的产品被抽滤,用甲醇洗涤和干燥。获得了1.5g(理论的53%)具有下式的紫色粉末。
λmax(甲醇)=592nm
ε=30100l/mol cm
溶解度:在TFP(2,2,3,3-四氟丙醇)中>2%
玻璃状的膜
也适合的二氮杂半花青染料列于下表:
1)甲醇中,除非另外指明
2)Δλ=|λ二氯甲烷-λ甲醇|
3)在短波斜坡上
4)在长波斜坡上
实施例39
在室温下制备在2,2,3,3-四氟丙醇中的4重量%实施例27染料的溶液。该溶液通过旋转涂覆被涂覆到预先成槽的(preyrooved)聚碳酸酯基体上。预先成槽的聚碳酸酯基体通过注模以盘的形式生产。盘的尺寸和槽纹结构对应于DVD-R通常使用的那些。含有作为信息载体的染料层的盘用100nm的银蒸汽蒸镀。之后通过旋转涂覆涂覆可紫外固化的丙烯酸清漆并使用紫外灯固化。使用建造在光具座上和由用于产生线性偏振光的二极管激光器(λ=405nm),偏振敏感分束器,λ/4-片(plate)和具有0.65数值孔径NA的可移动式悬挂会聚透镜(调节透镜)构成的动态记录试验装置,进行数据记录(写)和读取的实验。由盘的反射层反射来的光借助以上提到的偏振敏感分束器由光路偶合并通过象散镜会聚到四象限检测器上。在V=2.6m/s的线性速度和Pw=13.2mW的记录(写)功率下测量到信号/噪音比率C/N=42dB。记录功率被作为振荡脉冲序列应用,该盘交替用以上提到的记录功率Pw照射1μs和读功率Pr≈0.44mW照射4μs。该盘用这种振荡脉冲序列照射直到它已经完全旋转一次。之后产生的标记用读功率Pr≈0.44mW读并测定以上提到的信号/噪音比率C/N。
类似地使用上表中的其它的例子获得光学数据存储介质。
Claims (12)
1.包含优选透明的基体的光学数据存储介质,该基体任选已经被一个或多个反射层涂覆并且在其表面涂覆有光可记录的信息层,任选一个或多个反射层和任选保护层或另外的基体或上层,该数据存储介质可以使用蓝或红光,优选激光记录和读取,其中信息层包含吸光化合物和任选粘合剂,特征在于至少一种二氮杂半花青染料被用作吸光化合物。
2.根据权利要求1的光学数据存储介质,特征在于半花青对应于下式(I),
其中
K代表具有下式(II)到(IV)的基团,
X1代表O或S,
X2代表O,S,CH或N-R2,
X3代表N,CH或C-CN,
R1,R1和R12彼此独立地代表C1-到C16-烷基,C3-到C6-链烯基,C5-到C7-环烷基或C7-到C16-芳烷基,
A与X2和其中连接的碳原子一起代表可以包含1-4个杂原子和/或可以被苯并或萘并稠合和/或被非离子基团取代的五元芳族或准芳族杂环,
R3,R4,R5和R6彼此独立地代表氢,C1-到C16-烷基,C4-到C7-环烷基,C7-到C16-芳烷基或杂环基团或
NR3R4或NR5R6彼此独立地代表通过N相连和可以另外包含N或O原子和/或被非离子基团取代的五元或六元饱和环,
R7代表氢,C1-到C16-烷基,C1-到C16-烷氧基或卤素或
R7和R5形成可以包含O或N原子和/或被非离子基团取代的二元或三元桥,
R8代表氢,C1-到C16-烷基,C1-到C16-烷氧基,卤素,氰基,C1-到C4-烷氧羰基,O-CO-R10,NH-CO-R10,O-SO2-R10或NH-SO2-R10,
R9代表氢,C1-到C4-烷基或C6-到C10-芳基,
R10代表氢,C1-到C16-烷基,C4-到C7-环烷基,C7-到C16-芳烷基,C1-到C16-烷氧基,单-或双-C1-到C16-烷基胺基,C6-到C10-芳基,C6-到C10-芳氧基,C6-到C10-芳基胺基或杂环基团,
R11代表氢,C1-到C4-烷基或C6-到C10-芳基和
An-代表阴离子。
3.根据权利要求2的光学数据存储介质,特征在于在式(I)中
具有下式的环A
特别优选代表噻唑-2-基,苯并噻唑-2-基,苯并噁唑-2-基,苯咪唑-2-基,咪唑-2-基,吡唑-3-基,1,3,4-***-2-基,1,3,4-噻二唑-2-基,1,2,4-噻二唑-5-基,2-或4-吡啶基或2-或4-喹啉基,其中以上提到的环每一个可以通过以下取代:C1-到C6-烷基,C1-到C6-烷氧基,氟,氯,溴,碘,氰基,硝基,C1-到C6-烷氧羰基,C1-到C6-烷硫基,C1-到C6-酰胺基,C6-到C10-芳基,C6-到C10-芳氧基,C6-到C10-芳羰基胺基,单-或双-C1-到C6-烷基胺基,N-C1-到C6-烷基-N-C6-到C10-芳基胺基,吡咯子基,吗啉代或哌嗪子基。
4.根据权利要求2到3的一项或多项的光学数据存储介质,特征在于二氮杂半花青对应于式(I),
其中
具有下式的环A
代表噻唑-2-基,苯并噻唑-2-基,其中X2代表S和以上提到的基团每一个可以通过甲基,乙基,甲氧基,乙氧基,氯,氰基,甲氧羰基或乙氧羰基取代,或代表1,3,4-***基或1,3,4-噻二唑基,其中X2代表N-R2或S,并且以上提到的基团每一个可以通过以下取代:甲基,乙基,苯基,甲氧基,乙氧基,甲硫基,乙硫基,氨基,苯胺基,二甲基胺基,二乙基胺基,二丙基胺基,二丁基胺基,N-甲基-N-氰代乙基胺基,N-甲基-N-羟基乙基胺基,N-甲基-N-苯基胺基,双-(氰代乙基)胺基,双-(羟基乙基)胺基,氰代乙基胺基,羟基乙基胺基,吡咯子基,哌啶子基,吗啉代或具有下式的基团,
K代表具有式(II),(III)或(IV)的基团,
X1代表O或S,
X3代表N,CH或C-CN,
R1,R2和R12彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,苯乙基,苯丙基,烯丙基,环己基,氯乙基,氰代甲基,氰代乙基,氰代丙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,
R3,R4,R5和R6彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,苯乙基,苯丙基,环己基,氯乙基,氰代甲基,氰代乙基,氰代丙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基,乙酸基乙基,丙酸基乙基或具有下式的基团
并且R3和R5可以另外代表氢或
NR3R4或NR5R6彼此独立地代表吡咯子基,哌啶子基,N-甲基哌嗪子基,N-乙基哌嗪子基,N-羟基乙基哌嗪子基或吗啉代,
R7代表氢,甲基,甲氧基或氯或
R7;R5代表-(CH2)2-,-(CH2)3-,-C(CH3)-CH2-C(CH3)2-或-O-(CH2)2-桥,
R8代表氢,甲基,甲氧基或氯,
R9代表氢,
R11代表氢,甲基或苯基和
An代表阴离子。
5.根据权利要求1到4的一个或多个的光学数据存储介质,特征在于二氮杂半花青对应于下式(VI)到(IX),
其中
R1和R2彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代甲基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基或具有下式的基团,
R5和R6彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基或乙酸基乙基或
NR5R6代表吡咯子基,哌啶子基或吗啉代,
R7代表氢或
R7;R5代表-(CH2)2-,-C(CH3)-CH2-C(CH3)2-或-O-(CH2)2-桥,
R8代表氢,
R13,R14和R15彼此独立地代表氢,甲基,甲氧基,氯,硝基或氰基,
R16和R17彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基,乙酸基乙基或苯基和
R16另外代表氢或
NR16R17代表吡咯子基,哌啶子基或吗啉代,和
An代表四氟硼酸根,高氯酸根,六氟硅酸根,六氟磷酸根,碘阴离子,硫氰酸根,氰酸根,羟基乙酸根,甲氧基乙酸根,乳酸根,柠檬酸根,甲磺酸根,乙磺酸根,苯磺酸根,甲苯磺酸根,丁基苯磺酸根,氯苯磺酸根,十二烷基苯磺酸根或萘磺酸根,
其中所有的烷基基团可以是支链的。
6.根据权利要求1到4的一个或多个的光学数据存储介质,特征在于二氮杂半花青对应于下式(X)到(XIII),
其中
R1和R2彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代甲基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基或具有下式的基团,
X1代表O和
X3代表CH或
X1代表S和
X3代表N,CH或C-CN,
R3和R4彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基或乙酸基乙基或
NR3R4代表吡咯子基,哌啶子基或吗啉代,
R9代表氢,
R13,R14和R15彼此独立地代表氢,甲基,甲氧基,氯,硝基或氰基,
R16和R17彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基,乙酸基乙基或苯基和
R16另外代表氢或
NR16R17代表吡咯子基,哌啶子基或吗啉代,和
An-代表四氟硼酸根,高氯酸根,六氟硅酸根,六氟磷酸根,碘阴离子,硫氰酸根,氰酸根,羟基乙酸根,甲氧基乙酸根,乳酸根,柠檬酸根,甲磺酸根,乙磺酸根,苯磺酸根,甲苯磺酸根,丁基苯磺酸根,氯苯磺酸根,十二烷基苯磺酸根或萘磺酸根,
其中所有的烷基基团可以是支链的。
7.根据权利要求1到4的一个或多个的光学数据存储介质,特征在于二氮杂半花青对应于下式(XIV)到(XVII),
其中
R1,R2和R12彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,氰代甲基,氰代乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基或具有下式的基团,
R13,R14和R15彼此独立地代表氢,甲基,甲氧基,氯,硝基或氰基,
R16和R17彼此独立地代表甲基,乙基,丙基,丁基,戊基,己基,苯甲基,环己基,氯乙基,羟基乙基,2-羟基丙基,甲氧基乙基,乙氧基乙基,甲氧羰基乙基,乙氧羰基乙基,乙酸基乙基或苯基和
R16另外代表氢或
NR16R17代表吡咯子基,哌啶子基,或吗啉代,
R11代表氢,甲基或苯基和
An代表四氟硼酸根,高氯酸根,六氟硅酸根,六氟磷酸根,碘阴离子,硫氰酸根,氰酸根,羟基乙酸根,甲氧基乙酸根,乳酸根,柠檬酸根,甲磺酸根,乙磺酸根,苯磺酸根,甲苯磺酸根,丁基苯磺酸根,氯苯磺酸根,十二烷基苯磺酸根或萘磺酸根,
其中所有的烷基基团可以是支链的。
9.二氮杂半花青染料在可记录光学数据存储介质的信息层中的应用,其中半花青在420-650nm的范围具有吸收最大值λmax2。
10.二氮杂半花青染料在可记录光学数据存储介质的信息层中的应用,其中数据存储介质用蓝激光记录和读取。
11.生产根据权利要求1的光学数据存储介质的方法,其特征在于任选已经涂覆有反射层的优选透明的基体被半花青涂覆,任选与合适的粘合剂和添加剂和任选合适的溶剂组合,并任选提供反射层,另外的中间层和任选的保护层或另外的的基体或上层。
12.根据权利要求1的光学数据存储介质其使用蓝或红,特别是蓝光,和更特别是蓝激光记录和读取。
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
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DE10115227.2 | 2001-03-28 | ||
DE10115227A DE10115227A1 (de) | 2001-03-28 | 2001-03-28 | Optischer Datenträger enthaltend in der Informationsschicht eine lichtabsorbierende Verbindung mit mehreren chromophoren Zentren |
DE10136064.9 | 2001-07-25 | ||
DE2001136064 DE10136064A1 (de) | 2001-07-25 | 2001-07-25 | Optischer Datenträger enthaltend in der Informationsschicht einen Xanthenfarbstoff als lichtabsorbierende Verbindung |
EP01130527.3 | 2001-12-21 | ||
EP01130527 | 2001-12-21 | ||
EP02003812.1 | 2002-02-20 | ||
EP02003812 | 2002-02-20 |
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CN1513172A true CN1513172A (zh) | 2004-07-14 |
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CNA028108884A Pending CN1513172A (zh) | 2001-03-28 | 2002-03-20 | 在信息层中包含作为吸光化合物的二氮杂半花青染料的光学数据存储介质 |
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US (1) | US6726972B2 (zh) |
EP (1) | EP1386318A1 (zh) |
JP (1) | JP2004524201A (zh) |
CN (1) | CN1513172A (zh) |
TW (1) | TWI256634B (zh) |
WO (1) | WO2002089128A1 (zh) |
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CN101148546B (zh) * | 2006-09-22 | 2013-02-06 | 住友精化株式会社 | 光吸收染料组合物 |
CN112210229A (zh) * | 2019-07-12 | 2021-01-12 | 上海汇友精密化学品有限公司 | 一种阳离子液体染料的制备方法 |
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WO2003079339A1 (de) * | 2002-03-19 | 2003-09-25 | Bayer Chemicals Ag | Squaryliumfarbstoffe als lichtabsorbierende verbindung in der informationschicht von optischen datenträgern |
TW200504741A (en) * | 2003-06-27 | 2005-02-01 | Ciba Sc Holding Ag | Optical recording materials having high storage density |
AU2005249031A1 (en) * | 2004-06-03 | 2005-12-15 | Clariant Finance (Bvi) Limited | Use of squaric acid dyes in optical layers for optical data recording |
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US5547727A (en) | 1994-12-13 | 1996-08-20 | Eastman Kodak Company | Optical recording elements having recording layers containing cationic azo dyes |
DE4444863A1 (de) | 1994-12-16 | 1996-06-20 | Bayer Ag | Kationische 1,3,4-Thiadiazolfarbstoffe |
JP3523700B2 (ja) | 1995-01-12 | 2004-04-26 | 日亜化学工業株式会社 | 窒化物半導体レーザ素子 |
EP0757083A3 (de) | 1995-08-02 | 2000-01-12 | Ciba SC Holding AG | Kationische Thiazolazu- und Benzthiazolazofarbstoffe |
JP3558747B2 (ja) | 1995-08-03 | 2004-08-25 | 松下電器産業株式会社 | 記録再生装置 |
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JPH1058828A (ja) | 1996-08-16 | 1998-03-03 | Mitsui Petrochem Ind Ltd | 光記録媒体 |
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-
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- 2002-03-20 TW TW091105376A patent/TWI256634B/zh not_active IP Right Cessation
- 2002-03-20 US US10/102,578 patent/US6726972B2/en not_active Expired - Fee Related
- 2002-03-20 CN CNA028108884A patent/CN1513172A/zh active Pending
- 2002-03-20 EP EP02727442A patent/EP1386318A1/en not_active Withdrawn
- 2002-03-20 JP JP2002586340A patent/JP2004524201A/ja active Pending
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CN101148546B (zh) * | 2006-09-22 | 2013-02-06 | 住友精化株式会社 | 光吸收染料组合物 |
CN112210229A (zh) * | 2019-07-12 | 2021-01-12 | 上海汇友精密化学品有限公司 | 一种阳离子液体染料的制备方法 |
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JP2004524201A (ja) | 2004-08-12 |
EP1386318A1 (en) | 2004-02-04 |
US20030071268A1 (en) | 2003-04-17 |
US6726972B2 (en) | 2004-04-27 |
TWI256634B (en) | 2006-06-11 |
WO2002089128A1 (en) | 2002-11-07 |
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