CN101654510A - 高分子半导体 - Google Patents
高分子半导体 Download PDFInfo
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- CN101654510A CN101654510A CN200910166513A CN200910166513A CN101654510A CN 101654510 A CN101654510 A CN 101654510A CN 200910166513 A CN200910166513 A CN 200910166513A CN 200910166513 A CN200910166513 A CN 200910166513A CN 101654510 A CN101654510 A CN 101654510A
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- alkyl
- semiconducting polymer
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- 229920000642 polymer Polymers 0.000 title claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical group [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
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- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- -1 oxadiazole (bioxadiazole) Chemical compound 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
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- 229910000077 silane Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Abstract
一种式(I)的高分子半导体,其中X独立地选自S、Se、O和NR,其中R独立地选自氢、烷基、被取代的烷基、芳基、被取代的芳基、杂芳基和-CN;Ar独立地为共轭的二价部分;a为1至约10的整数;并且n为2至约5,000的整数。所得高分子半导体适于在有机薄膜晶体管中使用。
Description
技术领域
本发明在多个实施方案中涉及适于在电子装置例如薄膜晶体管(“TFT”)中使用的组合物和方法。本发明还涉及使用所述组合物和方法制成的构件或层,以及含有所述材料的电子装置。
背景技术
薄膜晶体管(TFT)是现代电子设备包括例如传感器、图像扫描器和电子显示装置的基本构件。使用当前主流硅技术的TFT电路对于一些应用来说可能成本过高,特别是对于其中高切换速度并非必需的大面积的电子装置,例如显示器的底板开关电路(例如活性基质液晶监视器或电视机)。基于硅的TFT电路的高成本主要是由于使用了资金密集型硅生产设备,以及需要对环境进行严格控制的复杂的高温、高真空光刻制造方法。通常希望制备不仅具有低得多的生产成本而且具有吸引人的机械性能例如结构紧凑、重量轻而且柔韧的TFT。有机薄膜晶体管(OTFT)可适于那些不需要高切换速度或高密度的应用。
TFT通常由一个支承基底、三个电传导电极(栅极、源极和漏极)、一个沟道半导体层,和一个将栅极与半导体层分开的电绝缘栅介电层组成。
改进已知TFT的性能让人期待。可通过至少三种性质来检测性能:迁移率、开/关电流比以及阈值电压。迁移率以cm2/V·s为单位测量;较高的迁移率是合乎需要的。较高的开/关电流比也是合乎需要的。阈值电压与为使电流流动而需要施加于栅极的偏压有关。通常,希望阈值电压尽可能接近于零(0)。
虽然对p型半导体材料进行了广泛的研究,但对n型半导体材料的关注却很少。具有高的电子迁移率和空气稳定性的n型有机半导体,尤其是可溶液加工的n-型半导体,由于同p型半导体相比具有空气敏感性并且难于合成,因此很稀少。由于n型半导体传输电子而非空穴,因此它们需要一个低的最低未占分子轨道(LUMO)能级。为实现低LUMO能级,已将吸电子基例如氟烷基、氰基、酰基或酰亚胺基施于一些n型有机半导体上。但是,这些吸电子基只可用作共轭核例如并苯、酞菁和低聚噻吩上的取代基或侧链,并且本身不可用作构成直链n型高分子半导体的共轭二价连接基。大多数报道的高迁移率空气稳定的n型半导体为小分子化合物并且只可使用昂贵的真空沉积技术进行加工来实现最大化性能。
发明内容
本发明在多个实施方案中涉及高分子半导体和具有一个含该高分子半导体的半导体层的薄膜晶体管。所述高分子半导体为在空气中稳定并且具有高迁移率的n型半导体材料,或者既为n型也为p型半导体材料。
实施方案中公开了一种式(I)的高分子半导体:
式(I)
其中X独立地选自S、Se、O和NR,其中R独立地选自氢、烷基、被取代的烷基、芳基、被取代的芳基、杂芳基和-CN;Ar独立地为共轭二价部分;a为1至约10的整数;并且n为2至约5,000的整数。
每一个Ar为选自以下的共轭二价部分
其中R’独立地选自氢、烷基、被取代的烷基、芳基、被取代的芳基、杂芳基、-CN等,或其混合。在具体的实施方案中,R’为烷基。如果合适,共轭的二价部分Ar可被烷基、被取代的烷基、芳基、被取代的芳基、杂芳基、卤素、-CN、-NO2等或其混合取代一次、两次或多次。
所述高分子半导体相对于真空可具有3.5eV或更小、或4.0eV或更小、或4.5eV或更小的LUMO。
在一些实施方案中,Ar可为
其中R1为具有1至约18个碳原子的烷基,或具有约5至约20个碳原子的芳基或杂芳基。
在另一些实施方案中公开了一种式(I)的高分子半导体:
式(I)
其中X独立地选自S、Se、O和NR,其中R独立地选自氢、烷基、被取代的烷基、芳基、被取代的芳基、杂芳基和-CN;每一个Ar独立地选自:
a为1至约10的整数;并且n为2至约5,000的整数。
在进一步的实施方案中还包括通过本方法制得的半导体层和/或薄膜晶体管。
本发明的示例性实施方案的这些及其他非限制性特征在下文进行更具体的描述。
附图说明
以下为附图的简要描述,所述附图的给出仅是为了说明本发明公开的示例性实施方案,而不是为了对其进行限制。
图1为本发明TFT的第一个示例性实施方案。
图2为本发明TFT的第二个示例性实施方案。
图3为本发明TFT的第三个示例性实施方案。
图4为本发明TFT的第四个示例性实施方案。
具体实施方式
参照附图可更全面地理解本发明公开的构件、方法和装置。所述附图仅为方便和易于说明本发明的示意图,因此,并不意在指明本发明的装置或构件的相对大小和尺寸和/或限定或限制示例性实施方案的范围。
虽然在以下描述中为清楚起见而使用了特定术语,但是这些术语仅意在指代为在附图中进行示例说明而选择的实施方案的具体结构,并不意在限定或限制本发明的范围。在以下的附图和下文描述中,应理解的是,相同的附图标记指代相同功能的构件。
本发明涉及式(I)的高分子半导体,其在下文进一步描述。所述高分子半导体特别适于在薄膜晶体管或有机薄膜晶体管(OTFT)的半导体层中使用。所述晶体管可具有多种不同的构型。
图1说明了第一个OTFT实施方案或构型。OTFT 10含有一个与栅极30和介电层40相接触的基底20。虽然此处栅极30被描绘为处于基底20中,但这并不是必需的。但是,介电层40将栅极30与源极50、漏极60和半导体层70分开则是较重要的。源极50接触半导体层70。漏极60也接触半导体层70。半导体层70设置在源极50和漏极和60之上和之间。任选的界面层80位于介电层40和半导体层70之间。
图2说明了第二个OTFT实施方案或构型。OTFT 10含有一个与栅极30和介电层40相接触的基底20。半导体层70设置于介电层40的上部或顶部并将介电层40与源极50和漏极60分开。任选的界面层80位于介电层40和半导体层70之间。
图3说明了第三个OTFT实施方案或构型。OTFT 10含有一个同时用作栅极并与介电层40相接触的基底20。半导体层70设置于介电层40的上部或顶部并将介电层40与源极50和漏极60分开。任选的界面层80位于介电层40和半导体层70之间。
图4说明了第四个OTFT实施方案或构型。OTFT 10含有一个与源极50、漏极60和半导体层70相接触的基底20。半导体层70设置在源极50和漏极60之上和之间。介电层40在半导体层70的顶部。栅极30在介电层40的顶部并且不接触半导体层70。任选的界面层80位于介电层40和半导体层70之间。
实施方案中公开了一种式(I)的高分子半导体:
式(I)
其中X独立地选自S、Se、O和NR,其中R独立地选自氢、烷基、被取代的烷基、芳基、被取代的芳基、杂芳基和-CN;Ar独立地为共轭的二价部分;a为1至约10的整数;并且n为2至约5,000的整数。
在具体的实施方案中,X独立地选自S和O。当X为硫时,半导体材料可被认为是一种二噻二唑(bithiadiazole)材料,当X为氧时,半导体材料可被认为是一种二噁二唑(bioxadiazole)材料。
每一个Ar部分可为选自以下的二价部分
及其结合,其中R’独立地选自氢、烷基、被取代的烷基、芳基、被取代的芳基、杂芳基、-CN等,或其混合。在具体实施方案中,R’为烷基。如果合适,所述共轭的二价部分Ar可被烷基、被取代的烷基、芳基、被取代的芳基、杂芳基、卤素、-CN、-NO2等,或其混合在外围取代一次、两次或多次。应注意的是,“Ar”表示一个部分的存在,而“a”表示所述部分的数目。换言之,可以具有不同的Ar部分,如下文所见。
在一些实施方案中,Ar可为
其中R1为具有1至约18个碳原子的烷基,或具有约5至约20个碳原子的芳基或杂芳基。参照Ar的含义,此处a=2。两个Ar部分均为具有一个侧链的噻吩,但R3侧链在一个噻吩上位于3位碳上,而在另一个噻吩上则位于4位碳上。
在另一些具体的实施方案中,每一个Ar部分独立地选自
在具体的实施方案中,所述高分子半导体相对于真空具有3.5eV或更小的LUMO。在更具体的实施方案中,高分子半导体相对于真空具有4.0eV或更小、或4.5eV或更小的LUMO。
在实施方案中,高分子半导体为n型半导体。换言之,该高分子半导体可传输电子。
在另一些实施方案中,高分子半导体既为n型也为p型半导体。即,该高分子半导体既可传输电子也可传输空穴。
得到的高分子半导体可具有约1,000至约1,000,000,或约5000至约100,000的重均分子量。
在具体的实施方案中,高分子半导体选自式(1)至(32):
其中R、R’、R1和R2独立地选自氢、烷基、被取代的烷基、芳基、被取代的芳基、杂芳基、-CN等,或其混合。在具体的实施方案中,R’为烷基。在另一些具体的实施方案中,R1不同于R2。
同样,参照Ar的含义,在式(32)中,a=3。Ar部分中的两个为具有一个侧链的噻吩(同样地,侧链连接于不同的碳上),第三个部分为二酮基吡咯并吡咯。
本发明的高分子半导体适宜用作n型半导体。这些聚合物的1,3,4-杂二唑部分为强吸电子基部分,其降低了所得高分子半导体的LUMO。二杂二唑部分应该比单杂二唑部分具有更强的接受电子的能力。此外,如对位置进行了编号的下图中所见,二杂二唑部分通过5和5’位置形成聚合物。
如此,在5和5’位置形成的键基本相互平行。这使所得所得的聚合物链为直链,从而增加了固体状态时分子堆积的有序性。该直链结构还导致两个杂二唑环和与其连接的相邻共轭单元之间较小的空间排斥。这使得聚合物主链高度共平面,进而再次使通过分子间pi-pi相互作用的分子堆积高度有序。
如果需要,半导体层还可含有另一种有机半导体材料。其他有机半导体材料的实例包括但不限于并苯,例如蒽、并四苯、并五苯、及它们被取代的衍生物、苝、富勒烯(fullerene)、低聚噻吩;其他高分子半导体例如三芳基胺聚合物、聚吲哚咔唑、聚咔唑、聚并苯、聚芴、聚噻吩,及其被取代的衍生物;酞菁例如铜酞菁或锌酞菁,及其被取代的衍生物。
半导体层为约5nm至约1000nm厚,尤其是约10nm至约100nm厚。半导体层可通过任何合适的方法形成。但是,半导体层通常由液体组合物例如分散液或溶液形成,然后将其沉积于晶体管的基底上。示例性沉积方法包括液相沉积例如旋涂、浸涂、刮涂(blade coating)、棒涂、筛网印刷、冲压、喷墨印刷等,及本领域已知的其他常规方法。
所述基底可由包括但不限于硅、玻璃板、塑料膜或薄片的材料组成。对于结构柔韧的装置,可使用塑料基底,例如聚酯、聚碳酸酯、聚酰亚胺薄片等。基底的厚度可为约10微米至超过10毫米,示例性厚度为约50微米至约5毫米——尤其对于柔韧的塑料基底,对于硬质基底例如玻璃或硅,厚度为约0.5至约10毫米。
栅极由电传导材料组成。其可为金属薄膜、传导聚合物膜、由传导油墨或糊剂制成的传导膜、或基底本身,例如重度掺杂的硅。栅极材料的实例包括但不限于铝、金、银、铬、铟锡氧化物、传导聚合物例如聚苯乙烯磺酸盐掺杂的聚(3,4-亚乙二氧噻吩)(PSS-PEDOT)、以及由炭黑/石墨或银胶体组成的传导油墨/糊剂。栅极可通过真空蒸发、溅射金属或传导性金属氧化物、常规平版印刷及刻蚀、化学气相沉积、旋涂、浇铸或印制、或其他沉积方法而制备。栅极的厚度,对于金属膜可在约10至约500纳米范围内,对于传导聚合物可在约0.5至约10微米范围内。
介电层通常可为无机材料膜、有机聚合物膜、或有机-无机复合膜。适于作为介电层的无机材料的实例包括氧化硅、氮化硅、氧化铝、钛酸钡、钡锆钛酸盐等。适宜的有机聚合物的实例包括聚酯、聚碳酸酯、聚乙烯基苯酚、聚酰亚胺、聚苯乙烯、聚甲基丙烯酸酯、聚丙烯酸酯、环氧树脂等。介电层的厚度取决于所用材料的介电常数,并且可为例如约10nm至约500nm。介电层可具有例如小于约10-12西门子每厘米(S/cm)的电导率。介电层使用本领域已知的常规方法形成,所述方法包括在形成栅极中所述的那些方法。
如果需要,可在介电层和半导体层之间设置一个界面层。当有机薄膜晶体管中的电荷传输发生在所述两层的界面处时,所述界面层可能会影响TFT的性能。示例性界面层可由硅烷形成,例如2008年4月11日提交的序列号为No.12/101,942的美国专利申请中所述。
适于用作源极和漏极的典型材料包括栅极材料中的那些,例如金、银、镍、铝、铂、传导聚合物和传导油墨。在具体的实施方案中,电极材料提供较低的对半导体的接触电阻。典型的厚度为例如约40纳米至约1微米,更具体的厚度为约100至约400纳米。本发明的OTFT装置含有半导体沟道。所述半导体沟道的宽度可为例如约5微米至约5毫米,具体的沟道宽度为约100微米至约1毫米。所述半导体沟道长度可为例如约1微米至约1毫米,更具体的沟道长度为约5微米至约100微米。
当向栅极施加例如约+10伏至约-80伏的电压时,可将源极接地并向漏极施加例如约0伏至约80伏的偏压来收集穿过半导体沟道传输的载流子。所述电极可使用本领域已知的常规方法来形成或沉积。
如果需要,也可在TFT的顶部沉积一个屏障层来保护其免受环境条件例如光、氧和湿气等的影响,这些可降低其电性能。所述屏障层为本领域已知并且可仅由聚合物组成。
OTFT的各个构件可以任意顺序沉积于基底上,如图中所见。术语“基底上”不应理解为要求每个构件直接接触基底。该术语应该解释为描述构件相对于基底的位置。但是,通常地,栅极和半导体层两者均应与介电层接触。此外,源极和漏极两者均应与半导体层接触。通过本发明的方法形成的高分子半导体可沉积于有机薄膜晶体管的任何合适的构件上从而形成该晶体管的半导体层。
所得晶体管在实施方案中可具有0.01cm2/V·s或更大的迁移率。
虽然对具体实施方案进行了描述,但是申请人或本领域其他技术人员,仍可想到目前无法预见或可能无法预见的替代、修改、改变、改进及基本等同的方案。因此,所提交的(也可能会进行修改)的权利要求书意在包括所有这些替代、修改、改变、改进及基本等同的方案。
Claims (9)
1.一种式(I)的高分子半导体:
式(I)
其中X独立地选自S、Se、O和NR,其中R独立地选自氢、烷基、被取代的烷基、芳基、被取代的芳基、杂芳基和-CN;
Ar独立地为共轭的二价部分;
a为1至约10的整数;并且
n为2至约5,000的整数。
2.权利要求1的高分子半导体,其中每一个X为O。
5.权利要求4的高分子半导体,其中R1为具有约4至约20个碳原子的烷基。
9.权利要求8的高分子半导体,其中R1为具有约4至约20个碳原子的烷基。
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US3238183A (en) * | 1963-01-28 | 1966-03-01 | Du Pont | Aromatic poly-1, 3, 4-oxadiazoles and process of making same |
DE19840195C1 (de) * | 1998-09-03 | 2000-06-15 | Fraunhofer Ges Forschung | Aromatische Poly(1,3,4-heterodiazole), Verfahren zu ihrer Herstellung und ihre Verwendung in optischen Vorrichtungen, insbesondere Elektrolumineszenzbauelementen |
DE60102456T2 (de) * | 2000-04-11 | 2005-03-03 | DuPont Displays, Inc., Santa Barbara | Lösbare poly(aryl-oxadiazol) konjugierte polymere |
JP3892795B2 (ja) * | 2002-10-31 | 2007-03-14 | 株式会社東芝 | ポリイミド光学材料、ポリイミド前駆体溶液、および光導波路素子 |
JP4066802B2 (ja) * | 2002-12-17 | 2008-03-26 | 富士ゼロックス株式会社 | ポリエステル樹脂及びそれを用いた機能素子、有機電界発光素子、並びに有機電界発光素子の製造方法 |
US20050146263A1 (en) * | 2003-09-25 | 2005-07-07 | Kelly Stephen M. | Lighting elements, devices and methods |
ES2387304T3 (es) * | 2003-10-28 | 2012-09-20 | Basf Se | Nuevos polímeros de dicetopirrolopirrol |
KR101069519B1 (ko) * | 2004-07-08 | 2011-09-30 | 삼성전자주식회사 | 올리고티오펜과 n-형 방향족 화합물을 주쇄에 교호로 포함하는 유기 반도체 고분자 |
CN1663971A (zh) | 2005-02-03 | 2005-09-07 | 华南理工大学 | 一种含硅杂环戊二烯的共轭聚合物及其应用 |
JP2006241267A (ja) * | 2005-03-02 | 2006-09-14 | Seiko Epson Corp | 導電性材料用組成物、導電性材料、導電層、電子デバイスおよび電子機器 |
US7758757B2 (en) * | 2007-10-19 | 2010-07-20 | E. I. Du Pont De Nemours And Company | Method for removing hydrazine compounds |
US7928433B2 (en) * | 2008-08-18 | 2011-04-19 | Xerox Corporation | Electronic device comprising semiconducting polymers |
US20160073171A1 (en) | 2014-09-05 | 2016-03-10 | Paul Wessel | Television enabled therapeutic communication systems and methods |
-
2008
- 2008-08-18 US US12/193,152 patent/US7928181B2/en active Active
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2009
- 2009-08-03 EP EP09167039A patent/EP2157114A1/en not_active Withdrawn
- 2009-08-11 CA CA2675188A patent/CA2675188C/en not_active Expired - Fee Related
- 2009-08-12 JP JP2009187132A patent/JP5103448B2/ja not_active Expired - Fee Related
- 2009-08-14 KR KR1020090075357A patent/KR101506349B1/ko active IP Right Grant
- 2009-08-17 CN CN2009101665139A patent/CN101654510B/zh not_active Expired - Fee Related
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CA2675188A1 (en) | 2010-02-18 |
EP2157114A1 (en) | 2010-02-24 |
JP5103448B2 (ja) | 2012-12-19 |
CN101654510B (zh) | 2013-06-26 |
US20100041861A1 (en) | 2010-02-18 |
KR20100021977A (ko) | 2010-02-26 |
CA2675188C (en) | 2013-04-30 |
KR101506349B1 (ko) | 2015-03-26 |
US7928181B2 (en) | 2011-04-19 |
JP2010045366A (ja) | 2010-02-25 |
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