CN1500266A - 光学记录介质及其制造方法 - Google Patents

光学记录介质及其制造方法 Download PDF

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CN1500266A
CN1500266A CNA028075730A CN02807573A CN1500266A CN 1500266 A CN1500266 A CN 1500266A CN A028075730 A CNA028075730 A CN A028075730A CN 02807573 A CN02807573 A CN 02807573A CN 1500266 A CN1500266 A CN 1500266A
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alkyl
aryl
recording medium
complex
metal
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A・扎菲罗夫
A·扎菲罗夫
品蛩够
S·拉科夫斯基
吉瓦-埃内瓦
J·巴卡吉瓦－埃内瓦
霍夫
L·普拉霍夫
诺瓦
L·阿塞诺瓦
嫉吓
F·马兰迪诺
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Vivastar Mastering & Materials AG
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Abstract

一种用于DVD－R型光学数据存储器的记录介质，其可以用波长630到680nm的激光束来读写，该记录介质含有一种亚酞菁(sPcY)用来吸收激光能量，该亚酞菁部分是以与二酚盐或三酚盐或与二－或三硫酚盐(bPh或tPh)组成的离子配合物形式，部分是以与阴离子的金属－硫羟－或金属－重氮－配合物(MK)的离子配合物形式存在的，所述离子配合物具有结构(I)和(II)，其中sPcY，sPcY’，sPcY”和sPcY’’’相同或不同。该记录介质显示出很高的稳定性且能用很高的记录速度来进行书写。

Description

光学记录介质及其制造方法
本发明属于光学数据存储器领域，并涉及到一种如第一个独立权利要求的前序部分所述的光学记录介质和一种相应独立权利要求前序部分所述的制备光学记录介质的方法。
已知的光学数据存储器具有一个圆盘状的，由透明塑料制成的载体，一个涂覆于载体之上的记录层和一个涂覆于记录层之上的反射层。所述载体在涂覆有记录层的那面上还具有螺旋形的记录槽。沿着该槽，利用作为记录光的激光来书写数据存储器。该过程中，记录层会受到局部改变，并在记录层和载体之间形成泡状坑穴。然后作为读取光的另一束激光扫描到被书写过的轨道，同时读取光的反射光作为读取信号记录到反射层上。
DVD-R(可记录数字化视频光盘)型和CD-R(可记录光盘)型的光学数据存储器的差别就在于前者的记录槽相互间设置得更为紧密且圆盘通常具有两个对半的载体，并在其间设置有记录层和反射层。为了读写DVD-R，所使用的激光的波长为630到680nm(CD-R：780nm)。相应的记录层由一种记录介质组成，并且该介质含有，比如，具有以下通式的，用于吸收激光能量的亚酞菁(Subphthalocyanin)-硼-化合物：
Figure A0280757300061
其中的A1到A12相互独立地为-H，-卤素，-烷基，-芳基，-烷基-芳基，-氧-烷基，-氧-芳基，-氧-烷基-芳基，-硫-烷基，-硫-芳基或-硫-烷基-芳基，同时所述的烷基具有1到20个碳原子并且所述的芳基是苯基-或萘基或它们的卤代衍生物，而其中的Y是硼。
X是，如在US-5776656的公开文本中所记载的，卤素，-OH，-OC2H5或-O-叔丁基。在该文本中推荐X还可以是苯基或苯氧基，优选是未被取代的。
记录层中还含有公知的猝灭剂，比如金属配合物(如金属-硫醇配合物)，以及必要时还可有稳定剂，如胺。
本发明的目的在于提供一种可用波长630到680nm的激光来读写的光学数据存储器，即，用于如DVD-R的基于亚酞菁基的记录介质，该介质相对于已知的那些记录介质，其特征在于有着极高的抗光和气候影响的稳定性，并且由本发明的记录介质形成的记录层可以以很高的速度来书写(极低的最佳记录能)。此外，本发明的目的还在于提供一种制备记录介质的方法。
这些目的可以通过如权利要求中所述的记录介质及其生产方法来实现。
本发明的记录介质含有用作吸收激光能量的化合物的一种具有硼或铝作为中心原子的亚酞菁。这种亚酞菁在本发明的记录介质中以离子配合物的形式存在，更确切的说，它部分是作为由两个或三个亚酞菁单元(sPcY-)和一个二酚盐或三酚盐或一个二或三硫酚盐(-bPh-或＞tPh-)组成的离子配合物，并且部分是作为由一个亚酞菁单元(sPcY-)和一个阴离子的金属-硫羟-或金属-重氮-配合物(MK)组成的离子配合物，即，本发明的记录介质包含以下离子配合物：
sPcY-bPh-YsPc’或 和sPcY-MK
其中：
sPcY，sPcY’，sPcY”和sPcY是相同或不同的亚酞菁并且具有以下的通式结构：
Figure A0280757300081
其中的A1到A12相互独立地为-H，-卤素，-烷基，-芳基，-烷基-芳基，-氧-烷基，-氧-芳基，-氧-烷基-芳基，-硫-烷基，-硫芳基或-硫-基-芳基，其中所述的烷基具有1到20个碳原子并且所述的芳基是苯基-或萘基或它们的卤素取代的衍生物，而Y是硼或是铝；
其中的bPh和tPh具有以下的通式结构：
该结构式中Z不存在，或代表-CH2-，-C2H4-，-S-，-O或-NH-，而位置Z’代表-(CnH(2-1)＜，其中的n＝1，2或3，或代表-N＜。并且其中每个苯环除了-O-或S-基团外还带有不超过两个其他的取代基R1到R6，而这其中的R1到R6可分别独立的代表-卤素，-CN，-NO2，-烷基，-芳基，-烷基芳基，-氧-烷基，-氧-芳基，-氧-烷基-芳基，-硫-烷基，-硫-芳基，-硫-烷基-芳基，-SO3H，-SO2H，-SO3N(烷基)2，-NH2，-NH(烷基)，-NH(芳基)，N(烷基)2，-N(芳基)2，其中所述的烷基具有1到8个碳原子而所述的芳基是-苯基或-萘基或它们的取代衍生物；
其中的MK是具有以下通式结构的金属-硫羟配合物或金属-重氮-配合物：
Figure A0280757300091
这里的M＝Ni，Co，Fe，Cu，Sn，Zn，Al，Ti，TiO，Cr，V，VO，Pt，Pd，Ge或Si，并且每个苯环带有不超过两个取代基R’1到R’8。而R’1到R’8又分别独立地为-卤素，-NO2，NH2，NH(烷基)，-NH(芳基)，N(烷基)2，N(芳基)2，-CN，-氧-烷基，-氧-芳基，-硫-烷基，硫-芳基，这里所述的烷基具有1到8个碳原子，而所述的芳基是-苯基或-萘基或它们的取代衍生物。
存在于本发明记录介质中的亚酞菁单元可以完全相同地被取代并且具有相同的中心原子Y(硼或铝)，或者它们可以不同地被取代并具有不同的中心原子Y。优选的方案是所有的亚酞菁单元中取代基A1到A4分别与取代基A5到A8和A9到A12相同。
优选的亚酞菁的例子具有以下取代基：
A1到A12＝-H(未取代的sPcY)；
A1，A4，A5，A8，A9，A12＝-辛基且A2，A3，A6，A7，A10，A11＝-H；
A2，A3，A6，A7，A10，A11＝-辛基且A1，A4，A5，A8，A9，A12＝-H；
A2或A3，A6或A7，A10或A11＝-S-辛基且其余为-H；
A2，A6，A10＝-苯氧基且其余＝-H；
A1，A5，A9＝-硫代苯氧基-(Thiophenoxy)且其余＝-H；
A1，A5，A9＝-氧-己基，A3，A7，A11＝-C1
在本发明的记录介质中，酚盐或不同酚盐的混合物可选自二酚盐或三酚盐或二硫酚盐或三硫酚盐。其中，在每个酚盐中取代基R1/R2优选和取代基R3/R4或R5/R6相同。
二酚盐和三酚盐或是-硫酚盐的优选例子是以下酚的阴离子：
2，2’-亚甲基-二(6-叔丁基-4-甲基酚)，
2，2’-亚甲基-二(6-叔丁基-4-乙基酚)，
2，2’-亚甲基-二(4，6-二甲基酚)，
2，2’-亚异丁基-二(4，6-二甲基酚)，
2，2’-亚甲基-二(4-甲基-6-α-环己基酚)，
4，4-亚甲基-二(2，6-二叔丁基酚)，
4，4’-亚丁基-二(6-叔丁基-3-甲基酚)
2，2’-硫-二(6-叔丁基-4-甲基酚)
2，2’-硫-二(4-甲基-6-α-甲基苄基苯酚)，
2，2’-硫-二(4，6-二-仲戊基苯酚)，
4，4’-硫-二(6-叔丁基-2-甲基酚)，
二-(4-羟基-3，5-二叔丁基苄基)-硫醚，
2，2’-二(5-二乙基氨基-酚)，
4，4’-二乙基-6，6’-二叔丁基-2，2’-双酚，
4，4’-二乙基-6，6’-二叔丁基-2，2’-双硫酚，
1，1，3-三(5’-叔丁基-4’-羟基-2’-甲基苯基)-丁烷。
优选的阴离子金属-硫醇配合物和金属-重氮-配合物如下述：
Figure A0280757300111
离子配合物(sPcY)2-bPh或(sPcY)3-tPh(由亚酞菁和二或三酚盐或-硫酚盐组成的离子配合物)和离子配合物sPcY-MK(由亚酞菁和阴离子的金属-硫羟配合物或金属-重氮配合物组成的配合物)之间的摩尔比在1∶99到99∶1之间。
除了酞菁-离子配合物外，记录介质中还可含有作为另外的吸收激光能的化合物的物质，如花青-，肉桂(Styril)-，甲-，重氮和/或金属化的重氮颜料。另外，还可以含有金属茂(如二茂铁)，乙酰丙酮化物-金属配合物，N，N’-四烷基-(或芳基)取代的对二氨基苯和/或喹啉，并且其重量份为不大于10份，以吸收激光能的化合物为100份计。
具有以硼或铝作为中心原子的亚酞菁的制备由相应的取代的1，2-二氰基-苯(邻苯二甲腈)与硼或铝的卤化物(优选是硼或铝的氯化物)反应来完成。该过程中要加入1，8-二氮杂二环[5.4.0]-7-十一碳烯(DBU)作为催化剂(优选与邻苯二甲腈的摩尔比为0.1∶2到约1∶2)。其中会形成一种亚酞菁卤化物。
然后，将亚酞菁卤化物分别一方面和过量的二-或三酚盐或-硫酚盐，另一方面和过量阴离子的金属-硫羟-配合物或金属-重氮-配合物(优选过量约5倍摩尔)溶于一种合适的、有机溶剂或溶剂混合物中，并在升高温度下搅拌较长时间(如60-100℃下搅拌5-50小时)。
然后用水洗涤水溶性的盐并将有机离子配合物分离，洗涤，通过重结晶或以其他合适的方式提纯并干燥。
为了制备记录层，将分开制得的记录介质的亚酞菁离子配合物以希望的比例——必要时还要加入另一些化合物——溶于有机溶剂中。记录介质的溶液通过，例如，“旋涂”而涂覆到聚碳酸酯制成的载体上，并干燥。在以这种方式制备的记录层上，通过例如“喷镀”涂覆一层由银、金或铝或所述金属的合金制成的反射层。然后必要时将它用一层保护漆层覆盖起来，这样得到的盘片借助一个粘结层与具有第二保护层的第二个载体相结合。
实施例1：未取代的亚酞菁-硼化合物的合成
在氮气氛下将干燥的1，2-二氰基苯(0.5g，0.04mol)和DBU(0.02mol)的悬浮于新精馏的氯苯(12ml)中。将悬浮液冷却至-3℃，由注射喷嘴慢慢加入20.5ml的1M氯化硼(BCl3)的正-己烷溶液。将黄绿色的固体慢慢地、并在强烈搅拌下加热至60℃，同时液体会呈现黑色。然后蒸馏出己烷并在100℃下再搅拌10分钟，颜色变成紫色。将液相分出，而固体则首先用石油醚(80-100℃)萃取，再用甲苯萃取两小时。所留下的棕色的固体从乙醇中重结晶，用石油醚洗涤并在350℃下升化。这样就得到了3.57g(64％)棕色粉末状产品：
UV(DMF)λ最大：562，302nm；IR(KBr)：1692，1611，1452，1384，1280，1195，1130，950，878，753，695，629cm-1；1H NMR(360MHz)(DMSO-d6)：δ8.85(6H，dd)，7.90(6H dd)；MS(EI 70eV，260℃)：m/z 464(M++Cl-H，4)，431(M+，20)，430(55)，429(18)，396(70)，267(10)，256(8)，215(5)，197.5(35)，139(15)。
实施例2：三硫代辛基取代的亚酞菁-铝化合物(配向异构体(Regioisomer)的混合物)的合成。
将干燥的4-硫代辛基-邻苯二甲腈(460g，1.79mmol)和DBU(1mmol)在氩气氛下悬浮于0.5ml氯苯中。通过导管以轻微的氩气过压将0.15ml(1.79mol)氯化铝加入该悬浮液(之前在-78℃下冷凝)。将混合物在室温下搅拌10分钟，然后在80℃下搅拌15分钟。经冷却后用己烷洗涤析出的黑色固体，过滤并用己烷/二氯甲烷(1∶1)在Al2O3上进行色谱纯化。这样得到201g(44％)的粘性、紫色化合物。
实施例3：由亚酞菁和二酚盐形成的离子配合物的制备
将摩尔量过量五倍的4，4’-二乙基-6，6’-二叔丁基-2，2’-双酚的钠盐添加到0.01mol 1，4，5，8，9，12-六辛基-sPc-硼溴化物于正丁醇中形成的5％溶液中。在80℃下搅拌所得到的溶液12小时，并冷却，接着倒入到冷水中。在这个过程中，有机成分会沉淀出来，而水溶性的无机盐进入溶液中。将所沉淀出的固体过滤，用水洗涤，从乙醇中重结晶并在真空下干燥。
实施例4：由亚酞菁和二硫酚盐形成的离子配合物的制备
将相对于亚酞菁5倍量的4，4’-二乙基-6，6’-二叔丁基-2，2’-双硫酚的钠盐添加到0.01mol 2，6，10-三苯氧基-sPc-硼溴化物于氯苯中形成的5％溶液中。将所得到的溶液在80℃下搅拌10小时。然后蒸馏掉溶剂，将存在的产品从乙醇中重结晶出来，并真空干燥。
实施例5：由亚酞菁和金属-重氮配合物形成的离子配合物的制备
将二-(2-羟基-5-硝基4’-二乙基氨基-重氮-酚)-TiO(II)四丁基铵溴化物添加到0.01mol 1，5，9-三硫代苯氧基-sPc-硼(III)溴化物于二甲基甲酰胺/H2O(95∶5)中形成的5％溶液中。将所得到的溶液在70℃下搅拌12小时，冷却并倒入到冷水中。其后的操作和实施例3中一样。
实施例6：由亚酞菁和金属-二硫羟配合物形成的离子配合物的制备
将二-1，2(4-甲氧基苯-1，2-二硫醇)-镍(II)四丁基铵溴化物添加到0.01mol1，5，9-三己基-氧基-3，7，11-三氯-sPc-硼(III)溴化物于二甲基甲酰胺/H2O(95∶5)中形成的5％溶液中。将所得到的溶液在70℃下搅拌15小时，冷却并倒入到冷水中。其后的操作过程如上面实施例3中所述进行。
实施例7：光学数据存储器的制备和测试
将实施例3-6中得到的含有亚酞菁的离子配合物用于制备DVD-R数据存储器。
在搅抖下，将含有分别制备、纯化和干燥的亚酞菁的离子配合物以及必要时另外的一些化合物以希望的份量比溶于一种有机溶剂或溶剂混合物(如2，2，3，3-四氟丙醇，2-乙氧基-乙醇，双丙酮醇/丁醇(10∶1)，双丙酮醇/异丙醇(10∶1)或乙基纤维素溶剂(Ethylcellosolve)中。溶液的浓度在0.5-5％(重量)的范围内。
必不可少的聚碳酸酯基质盘以喷模法生产(Φ120mm，厚0.6mm)。在基片的表面上压上一道槽距为0.74μm的螺旋槽。根据所使用的记录介质，选择槽深度在100-200nm范围内，而槽宽在180-400nm范围内。通过“旋涂”涂覆上记录层。槽内和槽间记录层的厚度要根据记录介质中吸收激光能的化合物的光学参数而分别在90-140nm和10-30nm的范围内变化。
将被涂层的聚碳酸酯载体紧接着在70到80℃下干燥。然后通过“喷镀”在经干燥的记录层上涂覆上一层厚度为70-120nm的反射金层。接着涂覆上一层保护漆层(厚约4μm)并在UV辐照下进行硬化。没有颜料和金属层的聚碳酸酯盘同样设置保护漆层。各将一个具有记录层、金属层和保护漆层的圆盘和只有保护漆层的盘，在应用合适的粘结剂的情况下将其中一个的保护漆层相互准确粘结到另一个的保护漆层上。
以相同的工艺和方法生产的对比数据存储器具有一个由Fuji Foto Film股份有限公司的三次甲基-花青颜料制成的记录层和一种猝灭剂(Q)(例如NipponKayako股份有限公司公司的IRG22)的盘片。所述的三次甲基-花青结构如下：
Figure A0280757300141
使用e-focus公司的测试仪用激光束(波长635nm；线性书写速度3.49m/s)对以上述方式制得的盘片进行书写和测量。然后测试其耐光和耐气候稳定性(根据ISO-105-B02-条件用空气冷却的氙气灯，和按照JEC68-2-2Ba和用C68-2-30Dd进行测试)。
所有具有用本发明的记录介质制成的记录层的数据存储器的耐光和耐气候性能测试值都符合标准。
在下表中概括性地将所测得的结果平均值与现有技术(根据US6168843，TDK公司和具有基于次甲基颜料的记录介质的对照盘所得到的最佳值)进行了比较。
具有由本发明的记录介质所制得的记录层的光学数据存储器，也可以成功地以650nm波长的激光束来进行读写，并且也能得到符合标准的参数。计算机模拟表明，具有由本发明的记录介质所制成的记录层的光学数据存储器也能用大于4X书写速度书写。
记录介质 光学记录能(mW) 调制(％) 反射率(％) 不稳定性(％)
根据US-6168843(TDK公司) 7.2  60  46  8.0
70％C1+20％C2+10％Q ＞12  -  -  -
(sPcY)2-bPh或(sPcY)3-tPh(1) 72  60  50  8.0
sPcY-Mthiolenk.(2) 7.0  64  48  7.9
sPcY-Mdiazok.(3) 6.9  68  47  7.8
15％(1)+85％(2) 6.7  70  48  7.6
5％(1)+95％(3) 6.4  71  47  7.5
10％(1)+30％(2)+60％(3) 6.4  71  48  7.5
30％C1+10％(1)+20％(2)+40％(3) 6.2  72  46  7.4
标准 6＜OSE＜12 ≥60 ＞45 ＜8.0

Claims (19)

1.用于光学数据存储器的记录介质，其可用波长630到680nm的激光束来读写，该记录介质含有一种亚酞菁(sPc Y)用来吸收激光能量，该亚酞菁部分是以与二酚盐或三酚盐或与二硫酚盐或三硫酚盐(bPh或tPh)组成的离子配合物形式，部分是以与阴离子的金属-硫羟-或金属-重氮-配合物(MK)组成的离子配合物形式存在的，该离子配合物具有以下结构：
sPcY-bPh-YsPc’或
Figure A0280757300021
和sPcY-MK
其中：
sPcY-，sPcY’，sPcY”-和sPcY4相同或不同并且具有以下的结构：
Figure A0280757300022
其中的A1到A12相互独立地为-H，-卤素，-烷基，-芳基，-烷基-芳基，-氧-烷基，-氧-芳基，-氧-烷基-芳基，-硫-烷基，-硫-芳基或-硫-烷基-芳基，其中所述的烷基具有1到20个碳原子并且所述的芳基是苯基或萘基或它们的取代衍生物，并且其中Y是硼或是铝；
其中的bPh和tPh具有以下的结构：
Figure A0280757300031
其中Z不存在，或代表-CH2-，-C2H4-，-S-，-O-或-NH-，而Z’代表-(CnH(2n-1))＜，其中的n＝1，2或3，或代表-N＜，并且其中每个苯环除了-O-或-S-基团外还带有不超过两个其它的取代基R1到R6，而R1到R6分别独立代表-卤素，-CN，-NO2，-烷基，-芳基，-烷基芳基，-氧-烷基，-氧-芳基，-氧-烷基-芳基，-硫-烷基，-硫-芳基，-硫-烷基-芳基，-SO3H，-SO2H，SO3N(烷基)2，-NH2，-NH(烷基)，-NH(芳基)，N(烷基)2或-N(芳基)2，其中所述的烷基具有1到8个碳原子而所述的芳基是-苯基或-萘基或它们的取代衍生物；
其中的MK是具有以下结构的至少一种化合物：
这里的M＝Ni，Co，Fe，Cu，Sn，Zn，Al，Ti，TiO，Cr，V，VO，Pt，Pd，Ge或Si，并且每个苯环带有不超过两个取代基R’1到R’8，而R’1到R’8又分别独立地为-卤素，-NO2，NH2，NH(烷基)，-NH(芳基)，-N(烷基)2，-N(芳基)2，-CN，-氧-烷基，-氧-芳基，-硫-烷基或硫-芳基，这里所述的烷基具有1到8个碳原子而所述的芳基是苯基或-萘基或它们的取代衍生物。
2.根据权利要求1的记录介质，其特征在于与二-或三-酚盐或-硫酚盐组成的离子配合物和与阴离子的金属-硫羟配合物或金属-重氮配合物组成的离子配合物之间的摩尔比在1∶99到99∶1之间。
3.根据权利要求1或2之一的记录介质，其特征在于亚酞菁具有至少部分相同的取代A1，A4，A5，A8，A9和A12以及相同的取代基A2，A3，A6，A7，A10和A11。
4.根据权利要求1至3之一的记录介质，其特征在于在二-或三-酚盐或-硫酚盐中的取代基R1和R2分别与取代基R3和R4相同且分别与取代基R5和R6相同
5.根据权利要求1至4之一的记录介质，其特征在于在金属-硫羟配合物或金属-重氮配合物中的取代基R1，R3，R5和R7相同，且取代基R2，R4，R6和R8也相同。
6.根据权利要求1至4之一的记录介质，其特征在于在金属-硫羟配合物或金属-重氮配合物中的取代基R1/R2＝R7/R8且R3/R4＝R5/R6。
7.根据权利要求1至6之一的记录介质，其特征在于该介质除亚酞菁外还含有至少一种其它可吸收激光能量的化合物。
8.根据权利要求7的记录介质，其特征在于其它可吸收激光能量的化合物是花青-，肉桂-，甲-，重氮-或金属化的重氮-顔料。
9.根据权利要求1至8之一的记录介质，其特征在于它还含有作为其它化合物的金属茂，乙酰丙酮化物-金属配合物，N，N’-四取代的对二氨基苯酚和/或喹啉。
10.一种DVD-R型光学数据存储器，具有一个由透明塑料制成的载体，一个反射层和一个设置在载体和反射层之间的记录层，其特征在于记录层是由权利要求1至9之一的记录介质组成的。
11.根据权利要求10的数据存储器，其特征在于在反射层朝向记录层的那面上设置另一个由透明塑料制成的层。
12.根据权利要求11的数据存储器，其特征在于反射层和第二塑料层各带有一层用粘结剂相互连结着的保护漆层。
13.根据权利要求10到12之一的数据存储器，其特征在于反射层由金，银，铝或金，银或铝的合金组成。
14.制备权利要求1至12之一的记录介质的方法，其特征在于记录介质的离子配合物是单独制备，提纯并干燥的，且然后将其以希望的比例一起溶于一种有机溶剂中。
15.根据权利要求14的方法，其特征在于离子配合物的制备通过亚酞菁-卤化物和过量的二-或三酚盐或-硫酚盐或金属-硫羟配合物或金属-重氮配合物的反应来实现。
16.根据权利要求15的方法，其特征在于所述的过量是五倍摩尔过量。
17.根据权利要求15或16之一的方法，其特征在于离子配合物的制备通过在60-100℃温度下搅拌5到50小时来完成。
18.根据权利要求15至17之一的方法，其特征在于亚酞菁-卤化物通过邻苯二甲腈和硼的卤化物或铝的卤化物在1，8-二氮杂二环[5.4.0]-7-十一碳烯(DBU)存在下反应制得。
19.根据权利要求18的方法，其特征在于DBU以与邻苯二甲腈的摩尔比为0.1∶2到1∶2的量使用。
CNA028075730A 2001-03-30 2002-03-25 光学记录介质及其制造方法 Pending CN1500266A (zh)

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JP2008216589A (ja) * 2007-03-02 2008-09-18 Orient Chem Ind Ltd μ−オキソ架橋−ホウ素サブフタロシアニン二量体を含有する光学膜
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CN103288838B (zh) * 2013-05-09 2016-07-06 西北大学 一种双核亚酞菁类物质的制备方法
US8981088B1 (en) * 2013-08-28 2015-03-17 Xerox Corporation Boron subphthalocyanine compounds and method of making
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