CN1554126A - 用于有机薄膜晶体管的表面改性层 - Google Patents
用于有机薄膜晶体管的表面改性层 Download PDFInfo
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- CN1554126A CN1554126A CNA028175387A CN02817538A CN1554126A CN 1554126 A CN1554126 A CN 1554126A CN A028175387 A CNA028175387 A CN A028175387A CN 02817538 A CN02817538 A CN 02817538A CN 1554126 A CN1554126 A CN 1554126A
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Abstract
提供一种有机薄膜晶体管,它包括插入门介电层和有机半导体层之间的自组装单层。所述单层是所述门介电层与自组装单层前体反应形成的产物。所述单层前体组合物的通式为X-Y-Zn,其中,X是H或CH3,Y是直链或支链C5-C50脂族或脂环族连接基、或者是包含芳基和C3-C44脂族或脂环族连接基的C8-C50基团;Z选自-PO3H2、-OPO3H2、苯并三唑基(-C6H4N3)、羰氧基苯并三唑(-OC(=O)C6H4N3)、氧苯并三唑(-O-C6H4N3)、氨基苯并三唑(-NH-C6H4N3)、-CONHOH、-COOH、-OH、-SH、-COSH、-COSeH、-C5H4N、-SeH、-SO3H、-NC、-SiCl(CH3)2、-SiCl2CH3、氨基、氧膦基;n是1、2或3,其前提是当Z是-SiCl(CH3)2或-SiCl2CH3时,n=1。还提供制造薄膜晶体管和包含薄膜晶体管的集成电路的方法。
Description
发明领域
本发明涉及性能改进的有机薄膜晶体管。更具体的是,本发明涉及在所述半导体和门介电层之间具有自组装单层的有机薄膜晶体管。
发明背景
对于以低成本电子部件为中心的各种应用,有机半导体是很重要的一种观点是,可合成该有机物,为各种器件提供必需的电子性能,并且该有机物也可制成使之能进行低成本卷式加工,而这种加工对于晶体硅微电子部件来说目前是不可能的。
有机电子器件中我们所关心的一个方面是有机半导体和另一器件层之间所形成的界面质量。已进行许多研究工作,使用自组装单层(SAM)和其它类型的“掺杂”触点来控制有机半导体金属触点的性质。目前控制所述半导体/介电层界面的尝试包括在氧化硅表面上使用六甲基二硅氮烷(HMDS)和硅烷偶合剂。已经使用包括在真空中放置长时间的复杂沉积工艺来将十八烷基三氯硅烷(OTS)涂布到热生长二氧化硅门介电材料上,由此影响晶体管性能。用于这一工艺的材料具有一些缺点,包括在所述气氛和介电层表面上对水敏感、由于材料中的交联与介电层的成键反应相竞争而导致不稳定,以及难以获得可重复的薄膜性能。EP 1042652 A2揭示了使用几种表面处理方法来提高用于薄膜晶体管(TFT)的SiOx上溶液浇注低聚噻吩的晶域大小,虽然所测迁移值通常低于所述未处理的对照物。
概述
本发明人研究了有机电子器件,并着眼于所述有机半导体和所述介电材料之间的界面上。他们发现了提高有机薄膜晶体管性质的材料和方法。本发明的有机薄膜晶体管也适于通过卷式加工来制造。
简短地说,本发明提供一种插入到门介电层和有机半导体层之间的自组装单层,所述单层是所述门介电层和所述自组装单层前体反应形成的产品,所述前体包含具有如下通式的组合物:
X-Y-Zn
式中,X是H或CH3;
Y是C5-C50直链或支链脂族或脂环族连接基,或者是包含芳基和C3-C44脂族或脂环族连接基的C8-C50直链或支链基团;
Z选自-PO3H2、-OPO3H2、苯并三唑基(-C6H4N3)、羰氧基苯并三唑(-OC(=O)C6H4N3)、氧基苯并三唑(-O-C6H4N3)、氨基苯并三唑(-NH-C6H4N3)、-CONHOH、-COOH、-OH、-SH、-COSH、-COSeH、-C5H4N、-SeH、SO3H、-NC、-SiCl(CH3)2、-SiCl2CH3、氨基、氧膦基;
n是1、2或3,其前提是当Z是-SiCl(CH3)2或-SiCl2CH3时,n=1。
各种薄膜晶体管构造可以是任意的。例如,有机半导体层在源电极和漏极之上时,所述源电极和漏极可以邻接所述门介电层,或者所述有机半导体层可以插入所述源电极、漏极和门介电层之间。
另一方面,本发明提供制造薄膜晶体管的方法,所述方法包括如下步骤:提供一种基片;在所述基片上形成门电极材料;在所述门电极材料上形成门介电层;形成自组装单层(SAM),使其邻接所述门介电层,所述单层可以是所述门介电层和所述自组装单层前体反应形成的产物,形成有机半导体层使之邻接所述单层,并且形成源电极和漏极,使之邻接所述有机半导体层。所述前体与有机薄膜晶体管器件如上所述。也提供了一种包括有机薄膜晶体管器件的集成电路。
本发明的优点提供有机薄膜晶体管是相比缺乏本发明特性的已知器件,其具有一种或多种改进特性。使用本发明,可以提高如阈电压、亚阈值斜率、通断率和电荷-载流子迁移率等性质。本发明提供的器件性能改进使得能够制造开关速度更快且加工条件更简单的更加复杂的电路。本发明也能够制造具有与带有小编辑部器件类似的性能的较大电路元件。由于不需要使用昂贵而精细的形成图形方法,具有较大细部尺寸的器件就不那么昂贵。
如本文所述,“一个”或者“所述一个”可以和“至少一个”互换使用,意指“一个或多个”改性元件。
本发明的其它特征和优点从本发明以下详述及权利要求书可以清楚看出。上述公开内容原理的概述并不是用于说明各说明性实例或本发明的各种实施方式。所述更具体的附图和详述举例说明了使用本文所述原理的某些优选实施方式。
附图简要说明
图1是本发明一个实施方式的截面示意图,未按比例绘制。
图2是本发明另一实施方式的截面示意图,未按比例绘制。
图3是本发明再一实施方式的截面示意图,未按比例绘制。
详述
通常,薄膜晶体管包括门电极、门电极上的门介电层、邻接所述门介电层的源电极和漏极、以及邻接所述门介电层、源电极和漏极的半导体层。具体地说,有机薄膜晶体管(OTFT)具有有机半导体层。
本发明所述的有机薄膜晶体管还包括插入所述门介电层和有机半导体层之间的自组装单层(SAM)。
参见图1,在本发明的一个实施方式中,在基片26上形成门电极12。在门电极12上形成一门介电层14。在门介电层14和有机半导体层18之间插入自组装单层16。形成源电极22和漏极24使之邻接有机半导体层18。
上述晶体管实施方式包括所述有机半导体层上的源电极和漏极。各种其它实施方式也在本发明的范围内,其中一些如下所述。
现在参见图2,在本发明另一实施方式中,在基片46上形成门电极32。在门电极32上形成门介电层34。源电极42和漏极44邻接门介电层34。在门介电层34和有机半导体层38之间插入自组装单层36。
现在参见图3,在本发明又一实施方式中,在基片66上形成门电极52、源电极62和漏极64。在门电极52上形成门介电层54。自组装单层56插入到门介电层54和有机半导体层58之间。门介电层54应包围门电极52,使门电极52与源电极62及漏极64电绝缘。门介电层54不必填满门电极52与源电极62和/或漏极64之间的整个区域,但是门介电层54必须包围门电极52。在这种情况下,门介电层54与源电极62和/或漏极64之间的区域中可以包括自组装单层56和/或有机半导体层58。
在制造、试验和/或使用过程中,所述基片可以支承所述OTFT。例如,可以选择一种基片来进行试验或筛选各种实施方式,而选择另一种基片作为商用实施方式。在一些实施方式中,所述基片并不为TFT提供任何必需的导电功能。这种类型的基片在所述文献中称为“不参与基片”。有用的材料可以包括有机或无机材料。例如,所述基片可以包括无机玻璃、陶瓷箔、聚合物材料、填充聚合物材料、涂覆的金属箔、丙烯酸类、环氧类、聚酰胺类、聚碳酸酯类、聚酰亚胺类、聚酮类、聚(氧-1,4-亚苯基氧-1,4-亚苯基羰基-1,4-亚苯基)(有时称为聚(醚醚酮)或PEEK)、聚降冰片烯类、聚苯醚、聚(萘二羧酸乙二酯)(PEN)、聚(对苯二甲酸乙二酯)(PET)、聚(苯硫醚)(PPS)和纤维增强的塑料(FRP)。
在本发明的一些实施方式中可以使用柔性基片。这样就可以进行卷式加工,就可以进行连续生产,就规模化经济和生产的经济性来说,优于平面和/或刚性基片。所选的柔性基片较好能绕着直径小于约50cm的圆柱周长卷绕,而不会变形或开裂。所选的基片更好是能绕着直径小于约25cm的圆柱周长卷绕,而不会变形或开裂。在一些实施方式中,所选的基片最好是能绕着直径小于约10cm,或者甚至是5cm的圆柱周长卷绕,而不会变形或开裂。用于使本发明柔性基片绕着具体的圆柱卷绕的作用力通常较小,例如仅用手,即不需要杠杆、机械、液压系统等辅助。优选的柔性基片可以绕着自身卷绕。
在本发明的一些实施方式中,基片是任选的。例如,在图1的实施方式中,当门电极12和/或门介电层14能为所得TFT所需应用提供足够支承时,就不需要使用基片26。此外,所述基片可以和临时支承物结合。在这种实施方式中,支承物可拆开地粘附或者机械固定于基片26上,例如当暂时需要支承物时,例如在制造、运输、试验和/或储存时。例如,柔性聚合物基片可以粘附到刚性玻璃支承物上,这种支承物可以除去。
所述门电极可以是任何可用的导电材料。例如,所述门电极可以包含掺杂硅或者金属如铝、铬、金、银、镍、钯、铂、钽和钛。也可以使用导电聚合物,例如聚苯胺、聚(3,4-亚乙基二氧噻吩)/聚(苯乙烯磺酸酯)(PEDOT∶PSS)。此外,可以使用这些材料的合金、组合以及多层结构。
在本发明的一些实施方式中,可以使用相同的材料来提供门电极功能,也可以为基片提供支承功能。例如,掺杂硅可以起到门电极和支承OTFT的作用。
在所述门电极上形成门介电层。这种门介电层使得所述门电极和OTFT器件的其余部件电绝缘。因此,所述门电极包含电绝缘材料。所述门介电层的介电常数应约为2以上,更好是约5以上。所述门电极的介电常数也可以很高,例如,80-100,甚至更高。用于门介电层的材料可以包括例如无机电绝缘材料。所述门介电层可以包含聚合物材料,如聚偏二氟乙烯(PVDF)、氰基纤维素、聚酰亚胺等,但是无机覆盖层较好包括粘结到所述自组装单层上的外层。
用于所述门介电层的具体材料例子包括锶酸盐、钽酸盐、钛酸盐、锆酸盐、氧化铝、氧化硅、氧化钽、氧化钛、氮化硅、钛酸钡、钛酸锶钡、锆酸酞酸钡、硒化锌和硫化锌。此外,也可以使用这些例子的合金、组合以及多层结构作为门介电层。这些材料中,优选氧化铝、氧化硅和硒化锌。
门介电层在OTFT中作为隔离层,或者通过将所述门材料氧化形成门介电层来形成在所述门上。
所述源电极和漏极通过门介电层与所述门电极隔开,而所述有机半导体层可以在源电极和漏极之上或之下。所述源电极和漏极可以是任何有用的导电材料。有用的材料包括上述用于门电极的那些材料中的大多数,例如,铝、钡、钙、铬、金、银、镍、钯、铂、钛、聚苯胺、PEDOT∶PSS、其它导电聚合物、其合金、其组合以及它们的多层结构。
所述薄膜电极(例如,门电极、源电极和漏极)可以通过任何有用的方法来形成,例如,物理蒸气沉积(例如,热蒸发、溅射)或者喷墨打印。这些电极图形的形成可以通过已知的方法如遮蔽掩模、相加光刻法、相减光刻法、打印、微接触打印以及图案涂布来完成。
用于有机半导体层的有用材料包括并苯。具体的例子包括蒽、萘、并回苯和并五苯。其它例子包括苝、富勒烯、酞菁、低聚噻吩和它们的取代衍生物。
所述有机半导体层可以通过任何有用的方法gadn,例如蒸气沉积、旋涂和打印技术。
所述自组装单层(SAM)插入到门介电层和有机半导体层之间。所述单层是所述门介电层与自组装单层前体反应形成的产物。
自组装单层前体提供形成自组装薄膜,通常是靶表面上单层薄膜的分子。自组装薄膜通常通过将自组装前体稀溶液涂布到所述基片上,或者暴露于包含所述前体的气相中,并进行成膜来制备。所述前体分子在基片上形成通常排列的分子膜。一旦形成,所述膜不会再次溶解在由其沉积的溶剂中。
通常,本发明单层前体并不需要能单独形成交联的形成单层的材料,如三官能硅烷,所述交联过程会和门介电层的吸附或成键反应相竞争。但是,可以使用具有能键合到门介电层的官能团并具有在SAM成形之后能形成交联的其它基团的材料。
所述单层前体包含具有如下通式的组合物:
X-Y-Zn
式中,X是H或CH3;
Y是C5-C50直链或支链脂族或脂环族连接基,或者是包含芳基和C3-C44脂族或脂环族连接基的C8-C50直链或支链基团;
Z选自-PO3H2、-OPO3H2、苯并三唑基(-C6H4N3)、羰氧基苯并三唑(-OC(=O)C6H4N3)、氧苯并三唑(-O-C6H4N3)、氨基苯并三唑(-NH-C6H4N3)、-CONHOH、-COOH、-OH、-SH、-COSH、-COSeH、-C5H4N、-SeH、-SO3H、-NC、-SiCl(CH3)2、-SiCl2CH3、氨基、氧膦基;
n是1、2或3,其前提是当Z是-SiCl(CH3)2或-SiCl2CH3时,n=1。
此处,任意门介电层和自组装单层前体中的官能团之间的反应较好是成键作用(例如,共价键或者离子键)。此处,自组装单层是指厚度约为5-30数量级的单分子层。
在优选的实施方式中,Y可以是饱和脂族基团、不饱和脂族基团、饱和脂环族基团以及不饱和脂环族基团,或者它们的组合,它们各自可以是直链或支链。
所述单层前体可以包含如下通式所示的组合物:
CH3-(CH2)m-PO3H2
式中,m是4-21的整数。
单体前体的具体例子包括1-膦酰基辛烷、1-膦酰基己烷、1-膦酰基十六烷以及1-膦酰基-3,7,11,15-四甲基十六烷。
一类本发明所用支链烃单层前体中的一种是1-膦酰基-3,7,11,15-四甲基十六烷。该类其它烃前体包括1-膦酰基-2-乙基己烷、1-膦酰基-2,4,4-三甲基戊烷以及1-膦酰基-3,5,5-二甲基己烷。所述1-膦酰基-3,7,11,15-四甲基十六烷可以由市售烯丙基醇前体通过还原链烯的双键、将醇转化为相应的溴化物、然后将溴化物转化成相应的膦酸来制备。更具体的是,1-膦酰基-3,7,11,15-四甲基十六烷可以通过将3,7,11,15-四甲基-2-十六碳烯-1-醇还原成3,7,11,15-四甲基-1-十六烷醇、将3,7,11,15-四甲基-1-十六烷醇转化成1-溴-3,7,11,15-四甲基十六烷、然后将所述1-溴-3,7,11,15-四甲基十六烷转化成1-膦酰基-3,7,11,15-四甲基十六烷来制得。这些合成转变过程使用本领域技术人员熟悉的材料和方法来完成。也可以使用3,7,11,15-四甲基-2-十六磷烯-1-醇以外的原料以及和上述不同的独特反应顺序来合成1-膦酰基-3,7,11,15-四甲基十六烷,以及其它这类支链烃单层前体中的其它前体,和所述具体例举的单层前体并且制备方法不应视为不适当的限制。
所述自组装单层前体可以通过任何已知方法放置在门介电层上。例如,所述前体可以通过涂布工艺如喷涂、旋涂、浸涂、凹版涂布、微接触打印、喷墨打印、烫印、转印和蒸气沉积放置。所述自组装单层前体可以和所述门介电层表面相互作用。所述相互作用或反应可以是瞬时的,或者需要一定时间,在这种情况下,提高温度可以减少所需的时间。当在所述门介电层上放置自组装单层前体溶液时,可以通过适用于所用材料的方法例如加热来除去溶剂。在沉积所述有机半导体之前,通常要清洗除去任何过量的单层前体。
在一个实施方式中,在放置单层前体之前,形成源电极和漏极使之邻接门介电层。然后,放置所述单层前体。在完成所述自组装单层之后,在源电极和漏极上以及邻接所述门介电层的自组装单层上形成所述有机半导体层。
本发明的有机薄膜晶体管(OTFT)具有一个或多个比已知有机薄膜晶体管有利的方面。这些优点是显而易见的,例如,电荷-载流子迁移率。本发明提供电荷-载流子迁移率比非本发明制造的没有本发明所述自组装单层的对比OTFT好的OTFT。本发明的OTFT的电荷-载流子迁移率较好至少比非本发明制造的对比OTFT的电荷-载流子迁移率好约25%,更好是至少好约50%,在某些实施方式中至少好约100%。本发明提高了电荷-载流子迁移率,同时使OTFT的其它性质保持在所需的范围内。例如,达到上述改进,同时使得阈电压在约25到-25V之间,亚阈值斜率低于约10V/十进制(绝对值),通断率至少约为104。
更具体的是,在用并五苯作为有机半导体的实施方式中,本发明提供电荷-载流子迁移率至少约为0.2cm2/Vs、更好是至少0.5cm2/Vs、甚至更好是至少1.0cm2/Vs的OTFT。在本发明的一些实施方式中,所述电荷-载流子迁移率为2.0cm2/Vs以上。
本发明提供阈电压约为-25到25V,较好是阈电压约为0到-10V,更好是约0到-5V的p-型半导体OTFT。本发明提供阈电压约为-25到25V,较好是阈电压约为10到0V,更好是约5到0V的n-型半导体OTFT。
本发明提供亚阈值斜率低于约10V/十进制(绝对值),较好是低于5V/十进制(绝对值),更好是低于约2V/十进制(绝对值)的OTFT。本发明提供通断率至少约为104,较好是至少约为105,更好是至少约为5×105,甚至更好是至少约106的OTFT。
这些性质可以进行各种组合。例如,在本发明的一个实施方式中,所述p-型半导体OTFT的电荷-载流子迁移率至少约为1cm2/Vs,负的阈电压,亚阈值斜率低于约5V/十进制(绝对值),且通断率至少约为105。
本发明也提供制造薄膜晶体管的方法,所述方法包括如下步骤:(a)提供一种基片;(b)在所述基片上形成门电极材料;(c)在所述门电极材料上形成门介电层;(d)形成自组装单层(SAM)使其邻接着所述门介电层,所述单层是所述门介电层和自组装单层前体的反应产物,所述前体包含通式为X-Y-Zn的组合物,上式中,X是H或CH3,Y是C5-C50直链或支链脂族或脂环族连接基,或者是包含芳基和C3-C44脂族或脂环族连接基的C8-C50直链或支链基团,Z选自-PO3H2、-OPO3H2、苯并三唑基(-C6H4N3)、羰氧基苯并三唑(-OC(=O)C6H4N3)、氧苯并三唑(-O-C6H4N3)、氨基苯并三唑(-NH-C6H4N3)、-CONHOH、-COOH、-OH、-SH、-COSH、-COSeH、-C5H4N、-SeH、-SO3H、-NC、-SiCl(CH3)2、-SiCl2CH3、氨基、氧膦基,且n是1、2或3,其前提是当Z是-SiCl(CH3)2或OR-SiCl2CH3时,n=1;(e)形成有机半导体层使之邻接所述单层;(f)形成源电极和漏极使之邻接所述有机半导体层。
所述有机半导体层在所述源电极和漏极之上或之下,如上述薄膜晶体管器件中所述的。本发明也提供包括许多本发明方法制得的OTFT的集成电路。
本发明还提供制备集成电路的方法,所述方法包括:提供许多上述的OTFT。因此,本发明包括一个或多个上述OTFT的器件。这种器件包括例如射频识别标签、用于有源矩阵显示器(activemetrixdisplay)的后连线板(backplane)、智能卡、存储器等。在包括本发明OTFT的器件中,这种OTFT通过本领域已知的方法进行连接。
制造本发明薄膜晶体管或集成电路的整个工艺可以在低于约450℃的最大基片温度下进行,较好是低于约250℃,更好是低于约150℃,甚至更好是低于约70℃,或者甚至在室温附近的温度下(约25℃)。一旦掌握本文所包含的发明知识,所述温度选择通常取决于本技术领域中已知的基片和加工参数。这些温度常低于传统集成电路和半导体的加工温度,它能使用任意种类的较便宜的基片,如柔性聚合物基片。因此,本发明也可以制造包含具有明显改进性能的有机薄膜晶体管的较便宜的集成电路。
本发明的目的和优点通过以下实施例来进一步说明,但是这些实施例中引用的具体材料和量、以及其它条件和细节不应限制本发明。
实施例
试验方法
A.薄膜厚度
使用单波长椭圆储藏振光法来评估表面处理有机薄膜的厚度。使用Gaertner Dualmode Automatic Ellipsometer,L116A型(Gaertner Co.,Skokie,IL)以70°入射角、632.8nm的波长从清洁基片上获得基片的值Psi和Delta(ψs和Δs)。将所述薄膜施加到所述基片上,并测量薄膜的值(ψf和Δf)。
使用椭圆藏振光法模型软件WVASE32(来自J.A.Woollam,Inc.,Lincoln,NE)来构建由1500Al2O3-10SiO2-Si组成的光学模型。对SiO2和Si层而言,使用典型的光学常数(软件中包括有)。拟合度的不浮动变量是Al2O3的厚度(d)和折射系数(n)。使用1500和n=1.77的起始值。通常最终的拟合值为1400-1700,n为1.56-1.60。
一旦ψs和Δs拟合,那么浮动变量(dAl2O3和nAl2O3)就不变。将有机层加入光学模型,在空气和介电层之间。该层的厚度变化,但是其折射指数固定在1.46。然后,所述有机层厚度变化,使最好地拟合ψf和Δf。这有机层厚度记录为所述自组装单层的厚度。
更多的信息可见Laibinis等的″Comparison of the structures andwetting properties of self-assembledmonolayers of normal-alkanethiolson the coinagemetal surfaces,Cu,Ag,Au″,J.Am.Chem.Soc.,第113卷,第7152-67页,1991。
B.水接触角(WCA)
使用视频接触角仪器(VCA-2500XE型,来自AST Products,Billerica,mA)测量静态、前进和后退时的水接触角。记录值是各试验表面上至少三滴两侧的测量值的平均值。这些测量值在静态和前进测量时的测不准估计值为±1°,在后退测量时为±2°。表面特征数据列于表I。
C.自组装单层质量
使用接触角和椭圆偏振光厚度数据以及例如Bain,等在J.Am.Chem.Soc.,第111卷,第321-35页,1989中所述的技术确定所述单层的结构和排列有序情况。本方法中,当前进水接触值为111-115°,后退角大于100°时,可能是为排列有序良好的甲基封端表面。当椭圆偏振光厚度约为分子计算长度的约70-100%(即对于1-膦酰基十六烷来说约18-19)时,所述膦酰基链烷分子的排列方向可能是基本上垂直于表面,其分子的甲基(-CH3)在空气/膦酰基链烷薄膜界面处,其膦酰基在膦酰基链烷薄膜/介电层界面处。相反,前进水接触角为100-110°,表明所述薄膜的链烷链排列有序较差,认为空气/膦酰基链烷薄膜界面由亚甲基(-CH2-)和甲基组成。
D.薄膜晶体管性能
在室温下空气中,使用本领域已知的技术如S.M.Sze,Physics ofSemiconductor Devices,第442页,John Wiley & Sons,New York,1981中所示的技术测试晶体管性能。使用半导体参数分析仪(4145A型,来自Hewlett-Packard,San Jose,CA),结果如下。
将漏电流(Id)的平方根作为门-源偏压(Vg)从+10V到-40V的函数作图,用于-40V的恒定源-漏偏压(Vd),且使用门介电层的比电容、沟道(chaunel)宽度和沟道长度由曲线的直线部分计算饱和场效应迁移率。这直线拟合的x轴外推值作为阈电压(Vt)。此外,将Id作为Vg的函数作图,该图得到沿包含Vt的曲线部分画直线拟合的曲线。该直线斜率的倒数就是亚阈值斜率(S)。所述通断率是Id-Vg曲线的最小值和最大值之间的差。
材料
前体
所述自组装单层前体1-膦酰基十六烷(CH3-(CH2)15-PO3H2)从OryzaLaboratories,Chelmsford,mA购得,1-膦酰基辛烷(CH3-(CH2)7-PO3H2)从AlfaAesar,Ward Hill,mA购得,1-膦酰基己烷从Organometallics,Inc.,EastHampstead,NH购得。
在那些得到的膦酸包含残留乙酯的情况中,使用本领域中技术人员已知的步骤通过在100℃下,在盐酸水溶液中水解残留酯,之后庚烷或甲醇中重结晶所述膦酸来纯化所述原料。
按以下所述的方法合成所述1-膦酰基-3,7,11,15四甲基十六烷(CH3-(CHCH3CH2CH2CH2)3CHCH3CH2CH2-PO3H2)自组装单层前体。材料均从例如AldrichChemicals,milwaukee,WI处购得。
往50.0g(169mmol)3,7,11,15-四甲基-2-十六碳烯-1-醇在200mL乙醇中的溶液中加入0.3g(3mmol)三乙胺和500mg碳-5%钯。将混合物保持在Parr氢气发生器的50psi(345kPa)氢气中24小时。过滤所述混合物,并浓缩,蒸馏得到41.7g(83%)3,7,11,15-四甲基-1-十六烷醇,为透明无色液体,在0.05mm Hg下沸点150-155℃。
往40.0g(134mmol)3,7,11,15-四甲基-1-十六烷醇和400mL 48%氢溴酸的混合物中缓慢加入40ml浓硫酸。并在100℃下加热所述反应混合物24小时,并将其倒入1.2L的水中。用己烷提取所述混合物,并用饱和NaHCO3水溶液洗涤所述合并的有机相,并用MgSO4干燥。将所述溶液浓缩至深色液体,它用己烷经过3英寸(7.6cm)二氧化硅洗提。浓缩洗提液,制得淡琥珀色的液体,并经球形冷凝器蒸馏,制得40.8g(84%)1-溴-3,7,11,15-四甲基十六烷,为透明无色液体,在0.06mmHg下的沸点为160-180℃。
在150℃下,加热21.69g(60mmol)1-溴-3,7,11,15-四甲基十六烷和25g(150mmol)亚磷酸三乙酯的混合物。18小时后,再加入20g(120mmol)亚磷酸三乙酯,并继续加热24小时。在0.05mmHg下沸点30-50℃下蒸馏乙基膦酸二乙酯和其它挥发性组分,并经球形冷凝器蒸馏浓缩物,得到23.51g(94%)1-(二乙基膦酰基)-3,7,11,15-四甲基十六烷,为透明无色液体,在0.05mm Hg下的沸点为190-230℃。
往14.6g(3mmol)1-(二乙基膦酰基)-3,7,11,15-四甲基十六烷在40mL二氯甲烷中的溶液中加入15.0g(98mmol)溴代三甲基硅烷。在室温下24小时后,将所述溶液浓缩成淡黄色液体,将所述甲硅烷基磺酸酯中间体溶解在100mL甲醇中。所得溶液在室温下搅拌30分钟,并浓缩成白色固体。重复在甲醇中的溶解过程以及浓缩过程两次,并从乙酸乙酯中重结晶,得到10.5g(83%)1-膦酰基-3,7,11,15-四甲基十六烷,为白色结晶,熔点为69-72℃。
最终产物和所有中间体的1H、13C和31P NMR光谱和所述目标化合物的结构一致。
基片
单晶<100>bc向硅片从Silicon Valleymicroelectronics,San Jose,California获得。通过化学蒸气沉积法将1500氧化铝层沉积在各片正面。将5000铝金属层蒸气沉积到各片的背面。在这种实施方式中,将覆盖有铝的掺杂片作为门电极,且当制备有机薄膜晶体管时氧化铝作为门介电层。
实施例1
将上述硅片基片一分为四,并置于UV/臭氧室(家用造型,短波UV)中5分钟来进行清洁。以300rpm旋涂0.1重量%的所述前体在纯乙醇中的溶液5秒,之后以2000rpm旋涂15秒,由此将所选的自组装单层前体(1-膦酰基十六烷)施加到所制得基片的氧化铝表面上。然后,在真空加热板上在150℃下加热所涂覆基片3分钟,然后在新鲜的乙醇中清洗,并在氮气流中干燥。结果在所述基片氧化铝层上得到自组装单层。
使用上述步骤测量所述涂覆样品上所得自组装单层的水接触角和涂层厚度。结果列于表1(下面)。
在恒定氮气流中,在减压条件下,在3-区炉(Thermolyne 79500管式炉,来自Barnstead Thermolyne,Dubuque,Iowa)中纯化并五苯(从Aldrich Chemical获得)。
在真空条件(约10-6乇(或1.33×10-4Pa))下,通过升华以每秒0.5的速度将所述纯化的并五苯沉积到自组装单层表面上,直到厚度达到500(由石英晶体微量天平测得)。然后,将钯或金源电极和漏极用遮蔽掩模到形成所述并五苯层上。所述器件尺寸为40微米沟道长度,1000微米沟道宽度。
制备许多OTFT,并对7个沉积试验中的每一个试验3-7个OTFT的代表样品。所述平均结果显示在表2中。例外结果出现在单个OTFT中,其电荷-载流子迁移率约3.7cm2/Vs,而其它值为所述平均值或其附近。
实施例2-4
如实施例1所述制备实施例2-4,所述前体选择如表所示改变。在实施例4中,使用0.5重量%前体溶液。
在实施例2(1-膦酰基-3,7,11,15-四甲基十六烷)中,制备许多OTFT,并试验对3个沉积试验的每一个试验3-6个OTFT的代表样品。平均值列于表2中。
在实施例3(1-膦酰基辛烷)中,制备许多OTFT,并对6个沉积试验的每一个试验1-4个OTFT的代表样品。平均值列于表2中。
在实施例4(1-膦酰基己烷)中,制备许多OTFT,并对3个沉积试验的每一个试验3个OTFT的代表样品。平均值列于表2中。
对比例1
相继使用丙酮、甲醇、2-丙醇和去离子水进行冲洗,由此清洁硅片基片,之后在加热板上100℃下加热3分钟,并置于UV/臭氧室(家用构型)中15分钟。如实施例1-4所述,测量WCA,结果列于表1中(下面)。
如实施例1-4所述,沉积并五苯和源电极、漏极。在对比例1(未进行表面处理)中,制备许多OTFT,并对40个沉积试验的每一个试验3-7个OTFT的代表样品。平均值列于表2中。
表1.厚度和水接触角
实施例 前体 厚度 静态 前进 后退
() WCA WCA WCA
1 1-膦酰基十六烷 19 109 116 103
2 1-膦酰基-3,7,11,15-四甲基十六烷 14 112 113 101
3 1-膦酰基辛烷 7 106 112 100
4 1-膦酰基己烷 4 100 106 93
对比例1 Al2O3对照物 - <40 <40 <40
表2.性能
迁移率 阈电压 亚阈值斜率
实施例 前体 通断率
(cm2/Vs) (V) (V/十进制)
2.056 -4.86 5.24 2.38
1 1-膦酰基十六烷
(0.89) (5.37) (6.86) ×106
1-膦酰基-3,7,11,15- 1.831 5.40 2.85 4.52
2
四甲基十六烷 (0.72) (7.86) (1.29) ×105
1.959 -1.93 1.95 3.57
3 1-膦酰基辛烷
(0.36) (2.43) (0.77) ×106
1.820 1.11 4.02 1.80
4 1-膦酰基己烷
(0.57) (3.57) (4.21) ×106
0.972 -6.72 1.72 8.74
对比例1 Al2O3对照物
(0.35) (3.23) (0.86) ×106
在表2中,括号中的数字是标准偏差。
为了进行比较,用OTS处理的已知器件具有很高的阈电压(60V以上),但OTFT仍旧可行,如Jackson等在Pentacene-Based Organic Thin FilmTransistors,IEEE Transactions on Electron Devices,第44卷,第1325-31页,1997中所述的。
在不背离本发明范围和原理的条件下,本发明的各种修改和替换对本领域的那些技术人员来说是显而易见的,应理解,本发明决不是限于上述的说明性
实施方式。
Claims (13)
1.一种有机薄膜晶体管(OTFT),它包括插入门介电层和有机半导体层之间的自组装单层,所述单层是所述门介电层与自组装单层前体反应形成的产物,所述前体包含如下通式的组合物:
X-Y-Zn,其中,X是H或CH3;
Y是直链或支链C5-C50脂族或脂环族连接基、或者是包含芳基和C3-C44脂族或脂环族连接基的C8-C50基团;
Z选自-PO3H2、-OPO3H2、苯并三唑基(-C6H4N3)、羰氧基苯并三唑(-OC(=O)C6H4N3)、氧苯并三唑(-O-C6H4N3)、氨基苯并三唑(-NH-C6H4N3)、-CONHOH、-COOH、-OH、-SH、-COSH、-COSeH、-C5H4N、-SeH、-SO3H、-NC、-SiCl(CH3)2、-SiCl2CH3、氨基、氧膦基;
n是1、2或3,其前提是当Z是-SiCl(CH3)2或-SiCl2CH3时,n=1。
2.权利要求1所述的薄膜晶体管,其特征在于,所述薄膜晶体管的阈电压约为-25到25V,亚阈值斜率低于约10V/十进制(绝对值),通断率至少约为104,电荷-载流子迁移率至少约比没有自组装单层的OTFT对照物好约25%。
3.权利要求1所述的薄膜晶体管,所述薄膜晶体管包括门介电层,所述门介电层包含无机电绝缘材料。
4.权利要求1所述的薄膜晶体管,所述薄膜晶体管还包括未参与的基片。
5.权利要求1所述的薄膜晶体管,所述薄膜晶体管包括门电极、源电极和漏极,它们各自包含选自掺杂硅、金属和导电聚合物的材料。
6.权利要求1所述的薄膜晶体管,其中,Y选自饱和脂族基团、不饱和脂族基团、饱和脂环族基团以及不饱和脂环族基团,或者它们的组合,它们各自可以是直链或支链。
7.权利要求1所述的薄膜晶体管,其特征在于,所述单层前体包含选自CH3-(CH2)m-PO3H2的组合物,该式中,m是4-21的整数。
8.权利要求1所述的薄膜晶体管,其特征在于,所述单层前体包含选自1-膦酰基己烷、1-膦酰基辛烷、1-膦酰基十六烷以及1-膦酰基-3,7,11,15-四甲基上六烷的组合物。
9.权利要求1所述的薄膜晶体管,其特征在于,所述有机半导体层包含选自并苯、苝、富勒烯、酞菁和低聚噻吩的材料。
10.一种集成电路,它包含权利要求1所述的许多薄膜晶体管。
11.一种组合物,所述组合物包含1-膦酰基-3,7,11,15-四甲基十六烷。
12.一种制造有机薄膜晶体管的方法,所述方法包括:
a)提供一种基片;
b)在所述基片上形成门电极材料;
c)在所述门电极材料上形成门介电层;
d)形成自组装单层使其邻接所述门介电层,所述单层是所述门介电层和自组装单层前体的反应产物,所述前体包含通式如下的组合物:
X-Y-Zn式中, X是H或CH3;Y是C5-C50直链或支链脂族或脂环族连接基,或者是包含芳基和 C3-C44脂族或脂环族连接基的C8-C50直链或支链基团;Z选自-PO3H2、-OPO3H2、苯并三唑基(-C6H4N3)、羰氧基苯并三唑(-OC(=O)C6H4N3)、氧苯并三唑(-O-C6H4N3)、氨基苯并三唑(-NH-C6H4N3)、-CONHOH、-COOH、-OH、-SH、-COSH、-COSeH、-C5H4N、-SeH、-SO3H、-NC、-SiCl(CH3)2、-SiCl2CH3、氨基、氧膦基;且n是1、2或3,其前提是当Z是-SiCl(CH3)2或-SiCl2CH3时,n=1;
e)形成有机半导体层使之邻接所述单层;
f)形成源电极和漏极,使之邻接所述有机半导体层。
13.一种集成电路,所述集成电路包括权利要求12所述方法制得的许多薄膜晶体管。
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- 2002-08-26 EP EP02768718A patent/EP1425806A2/en not_active Withdrawn
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- 2002-08-26 JP JP2003527816A patent/JP4511175B2/ja not_active Expired - Fee Related
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CN102723439A (zh) * | 2011-03-29 | 2012-10-10 | 中国科学院微电子研究所 | 基于有机场效应晶体管的存储单元、存储器及其制备方法 |
WO2015189701A3 (en) * | 2014-06-13 | 2016-03-10 | The Chinese University Of Hong Kong | Self-assembled monolayers of phosphonic acids as dielectric surfaces for high-performance organic thin film transistors |
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US9701698B2 (en) | 2014-06-13 | 2017-07-11 | The Chinese University Of Hong Kong | Self-assembled monolayers of phosphonic acids as dielectric surfaces for high-performance organic thin film transistors |
CN105636968B (zh) * | 2014-06-13 | 2019-05-10 | 香港中文大学 | 作为高性能有机薄膜晶体管的电介质表面的膦酸自组装单分子膜 |
CN109713125A (zh) * | 2018-12-27 | 2019-05-03 | 广州天极电子科技有限公司 | 一种晶体管及其制备方法 |
CN113488591A (zh) * | 2021-07-05 | 2021-10-08 | 南京大学 | 一种平面型无寄生电容的有机场效应晶体管及其制作方法 |
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EP1425806A2 (en) | 2004-06-09 |
TWI225708B (en) | 2004-12-21 |
KR20040029143A (ko) | 2004-04-03 |
US6433359B1 (en) | 2002-08-13 |
AU2002331736A1 (en) | 2003-03-24 |
WO2003023877A2 (en) | 2003-03-20 |
JP4511175B2 (ja) | 2010-07-28 |
WO2003023877A3 (en) | 2003-09-25 |
JP2005503026A (ja) | 2005-01-27 |
CN100407473C (zh) | 2008-07-30 |
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