CN101405884A - 制备掺杂的有机半导体材料的方法以及在该方法中使用的配方物 - Google Patents

制备掺杂的有机半导体材料的方法以及在该方法中使用的配方物 Download PDF

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CN101405884A
CN101405884A CNA2007800099547A CN200780009954A CN101405884A CN 101405884 A CN101405884 A CN 101405884A CN A2007800099547 A CNA2007800099547 A CN A2007800099547A CN 200780009954 A CN200780009954 A CN 200780009954A CN 101405884 A CN101405884 A CN 101405884A
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奥拉夫·蔡卡
安德利亚·卢克斯
迈克尔·利默特
霍斯特·哈特曼
安德烈·格吕辛
安斯加尔·维尔纳
马丁·安曼
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Abstract

本发明涉及用于制备掺杂的有机半导体材料的方法，所述方法包含如下步骤：(i)制备包含至少一种掺杂剂前体、至少一种待掺杂的有机材料和溶剂的溶液或悬浮液，(ii)将所述溶液或悬浮液施用于基材上并移除溶剂，(iii)通过施加活化能将掺杂剂前体转化为掺杂剂，其中所述掺杂剂前体是掺杂剂的二聚物、低聚物、聚合物、二螺化合物或多环，所述掺杂剂前体通过施加活化能解离为掺杂剂。

Description

制备掺杂的有机半导体材料的方法以及在该方法中使用的配方物
本发明涉及制备掺杂的有机半导体材料的方法以及可以在该方法中使用的配方物。
有机半导体在大量应用中正获得持续增加的应用范围，例如有机发光二极管(OLEDs)、有机太阳能电池、有机薄膜晶体管(TFTs)、射频识别标签(RFIDs)、传感器等。
由于有机材料与无机半导体材料相比具有出色的可加工性，因此有机材料被用于这些应用中。有机材料易于在真空中蒸发或易于由溶液处理，相反无机半导体如硅和砷化镓则由PECVD、外延工艺乃至在单晶晶片中处理。由于简单的工艺如旋涂或浸涂、印刷技术或者Langmuir-Blodgett技术可以用于制造层，因而由溶液处理将会导致成本的显著节约。而且，有机物不仅能提供简单的处理方法，而且与易碎的无机半导体材料相比还是柔韧性的。然而，无机半导体在导电性和载流子迁移性方面远优于有机材料，这使得无机半导体在许多应用中仍然是第一选择。
一种改进有机材料电性能的途径是有机半导体有意的氧化还原掺杂。此时，少量的强施主(受主)材料被加入到半导体主体。在主体材料中，掺杂剂经历与基质的化学反应而释放出负(正)电荷、即电子(空穴)到传输主体材料。当掺杂剂阳离子(阴离子)和主体阴离子(阳离子)形成时可发生这一情况。施主掺杂到传输层称为n-型掺杂，而受主掺杂到传输层称为p-型掺杂(这两个术语都类似用于无机半导体掺杂)。施主可以是具有低电离电位的化合物，受主可以是具有高电子亲和势的化合物。
通过使用这些载流子掺杂剂，在传输材料中自由、持久的(稳定状态的)载流子数量增加，这直接转化为掺杂材料更高的导电性。例如在OLED结构中使用了p-或n-掺杂的载流子传输层的PIN OLEDs证明了掺杂的传输层的有用性。通过这么做，由于载流子通过掺杂层的欧姆损耗减少以及由于电子进入掺杂层的注入势垒降低，器件的工作电压显著降低。
至今，这些载流子传输掺杂有机半导体材料的用途在某些场合限制于经由热蒸发基质材料和掺杂剂而产生的层。其原因可归于施主或受主与基质的化学反应显著地改变了材料的物理特性这一事实，例如反应后产生了基质与掺杂剂的库伦作用。由于真空蒸发的限制，丧失了有机半导体材料的一个优点，即易于由溶液处理。
由于反应立即发生并且导致形成电荷转移络合物/有机盐，基质和掺杂剂的混合物难以由溶液直接处理。这些生成物与有机材料相比具有完全不同的溶解性，这显著地限制了掺杂剂-基质溶液的可加工性。因而可发生掺杂相与未掺杂相的分离，使得难以浇铸均匀的膜。可能需要具有高极性的溶剂(比如水)来溶解掺杂相。由于这些溶剂有限的电化学窗口、有限的化学稳定性、对溶解材料有限的反应活性、在结构上对在前制备的结构的不相容性、以及在有机电子器件中残留溶剂的不利影响，它们通常造成难以进行处理。由于掺杂溶液中反应性物质与溶剂间的不期望的副反应，使掺杂溶液的储存寿命也可能变短。
本发明的一个目的是提供一种用于制备掺杂的有机半导体材料的方法，其克服了现有技术的缺点。尤其是，该方法能以任何简单和成本有效的方式实现，以便在基材上提供均匀的掺杂剂和有机材料的层。
通过具有权利要求1特征的方法实现了这一目的。根据本发明还提供了如权利要求14所述的配方物，其可在本发明的方法中使用。优选的实施方式公开在从属权利要求中。
令人惊讶地发现，可以容易地由溶液掺杂有机半导体材料，其中在溶液中提供特定种类的掺杂剂前体，所述溶液还含有待掺杂的有机材料。将溶液优选以膜的形式施用于基材后，该掺杂剂前体被活化以解离(cleaved)为真正的掺杂剂。可以通过任意的大量能量的形式实现这种活化，其适用于本目的且对本领域技术人员显而易见。
本发明中术语“二聚物”的含义包含由两个单价基或双基相互反应产生的化合物。
术语“低聚物”的含义包含由几个双基组成的化合物，其中双基的第一基团末端与别的双基的第一末端反应，并且由此产生的较大的双基的第二末端与别的双基的第二末端反应。
术语“聚合物”的含义包含具有比低聚物更多数目的引入的双基的化合物。
“二螺化合物”根据本发明是双基的分子内加成产物，所述双基的基团中心由那一种类的结构要素分开，这类所述结构要素连接携带碳原子的基团，所述碳原子即相互加成的碳原子。
术语“多环”的含义包含双基的分子内加成产物，所述双基的基团中心由那一种类的结构要素分开，这类所述结构要素连接基团携带的碳原子以外的至少一个其他碳原子(例如至少一个在α位的原子)。
在部分或完全排除掺杂剂前体转变为掺杂剂必需的活化能以便防止掺杂剂前体过早解离的前提下，制备溶液并将其施用于基材上、并移除溶剂，这对于本发明的方法是有益的。如果必要的话，可在活化掺杂剂前体之前进行进一步的制备步骤，这是本领域技术人员所公知的。
掺杂剂前体转变为掺杂剂后，该掺杂剂将经历与基质的电荷转移。在n-型掺杂的情况下，掺杂剂将给予基质至少一个电子。结果基质将是带负电荷的。同样掺杂剂将是带单个(或多个)正电荷的。在p-型掺杂的情况下，掺杂剂将从基质接受至少一个电子。结果基质将是带正电荷的。同样掺杂剂将是带单个(或多个)负电荷的。
接下来，掺杂的细节将在n-型掺杂的实施例中解释。P-型掺杂的机理相似。
掺杂剂前体的活化时经历化学键不可逆的解离，使得与待掺杂的有机材料反应的氧化还原活性物质被释放，使得该有机材料被掺杂。有机材料的掺杂应理解为基于氧化还原化学而非基于酸/碱化学。为了避免酸/碱化学，尤其优选解离时没有氢或(路易斯)酸被释放。我们知道质子或酸能导致在有机材料中的p-型掺杂效果。因此氢或酸的释放可以导致对n-型掺杂效果不利的补偿。该化学键不可逆的解离据信是由于掺杂剂前体或基质的激发，接着从掺杂剂前体到基质的发生电子转移。于是该掺杂剂前体被氧化。据信该掺杂剂前体在氧化态经历不可逆的键解离。形成了自由基掺杂剂和/或掺杂剂阳离子。键解离不可逆的性质阻止了电子传递回来并稳定了掺杂状态。
如果使用p-型掺杂的掺杂剂前体，尤其优选解离时没有(路易斯)碱被释放。我们知道碱能导致在有机材料中的n-型掺杂效果。这导致对有意的p-型掺杂效果不利的补偿。
在本发明优选的实施方式中，用于n-型掺杂的掺杂剂前体仅由类似于施主的部分组成，其在掺杂剂前体解离期间释放出。在尤其优选的实施方式中，所述类似于施主的部分是相同的。对于p-型掺杂，优选掺杂剂前体仅由类似于受主的部分组成，其在活化期间释放出。
优选溶液的溶剂有低的极性。所述溶剂可以选自例如甲苯、四氢呋喃或二氯甲烷。溶剂的低极性使在溶液中掺杂剂前体和基质的未反应状态得到稳定。
在本发明优选的实施方式中，溶液在储存或者处理层期间保持在暗处和/或冷却。
只要没有施加适合的用于解离的活化能，本发明允许由溶液处理，因为在溶液中没有盐形成。使用该方法可以由溶液制备层，例如通过标准的涂覆或印刷技术。
掺杂的有机材料的一个要求，例如在OLEDs中，是在发射区域产生的激子具有足够高以产生可见光的能量。需要用于在波长400～475nm的蓝色光谱范围发射的最高能量。为了避免在OLED器件中另外的注入势垒，理想地应仔细选择空穴传输层和电子传输层的能级，使得该能级与发射区域相匹配。
在这方面，材料的还原电势可以相对于Fc/Fc+的电压值的形式提供。Fc/Fc+表示二茂铁/二茂铁离子参考对。还原电势例如可在合适的溶剂如乙腈或四氢呋喃中通过循环伏安法测量。循环伏安法以及其他用于确定还原电势和二茂铁/二茂铁离子参考对与各种参比电极关系的方法的细节可以在A.J.Bard et al.，“Electrochemical Methods：Fundamentals and Applications(电化学方法：原理及应用)”，Wiley，第二版，2000中找到。
另一可选择的对于施主掺杂剂分子的氧化强度的测量可以是紫外光电子能谱法(UPS)。电离电位通过这种方法确定。但必须区分实验是在气相还是在固相中进行，即通过研究该材料的薄膜来区分。在后一种情况下，与气相相比较，固态效果比如移除光电子后在固体中残留的空穴的极化能量，会引起电离电位的偏移。通常极化能量的值为约1eV(E.V.Tsiper et al.，Phys.Rev.B 195124/1-12(2001))。
对于在OLED中通常的电子传输材料，其相对于Fc/Fc+的还原电位为约-2.3V。对于在太阳能电池中通常的电子传输材料，其相对于Fc/Fc+的还原电位为约-1V。对于在OLED中通常的空穴传输材料，其相对于Fc/Fc+的氧化电位为约0.2V。
n-型掺杂剂相对于Fc/Fc+的氧化电位等于或小于约-1V，优选等于或小于-2.0V，更优选等于或小于-2.2V。
p-型掺杂剂相对于Fc/Fc+的还原电位等于或大于0V。
对于本发明优选基质和掺杂剂前体在溶液中不会自发起反应，而仅在适当的活化后反应。据信如果掺杂剂前体的氧化电位Vox_DP和基质的还原电位Vred_Mat接近的话，可以发生从掺杂剂前体和基质自发的电子转移。作为一个实例，10c，10c’-双(8，9-二甲基-2，3，5，6-四氢-1H，4H-3a，6a，10b-三氮杂-荧蒽基)(二聚物)在室温下甚至在没有光照时能与萘四羧酸二酐(NTCDA)自发反应。10c，10c’-双(8，9-二甲基-2，3，5，6-四氢-1H，4H-3a，6a，10b-三氮杂-荧蒽基)相对于Fc/Fc+的氧化电位是-0.74V(四氢呋喃中)，NTCDA相对于Fc/Fc+的还原电位是约-0.79V(二氯甲烷中)。因而优选Vox_DP-Vred_Mat至少大于0.05V，优选大于0.2V，更优选大于1V。较大的差值因增加了该方法的能垒，从而降低了热电子转移的速度。溶液变得易于在室温操作，并且仅在被光辐照时就会被活化。选择相应的能级使得仅在高能量的光(例如蓝色)下而不在低能量的光(例如黄色)下活化是有益的。这有助于在观察到黄色光条件的通常生产设备中操作。该方法能让操作者可视地监督而防止了过早的活化。
而且，有益的是在解离期间掺杂剂前体仅释放某些最小尺寸的成分。在这种情况下，层内掺杂剂的扩散或者向相邻层的扩散被阻碍或者甚至被阻止。因而优选掺杂剂由至少两个环组成，更优选由至少三个环组成。这些环可以相互键结或稠合，可以是饱和或不饱和的。它们可以包含或不包含杂原子。还优选掺杂剂由至少15个原子组成，更优选由至少35个原子组成。掺杂剂的摩尔质量优选大于100g/mol，更优选大于200g/mol。应该理解，对于掺杂剂前体，其相应地是这些重量或尺寸值的至少两倍。
根据本发明合适的用于形成掺杂层的基质材料可以是小分子电子传输材料，比如主族金属的喹啉络合物，酞菁络合物，卟啉络合物，菲咯啉化合物，噁二唑化合物，杂芳族化合物尤其是N-杂芳族化合物，及其混合物。尤其适合的是如下所述的共轭聚合物或低聚物，其中x和y在0到5之间变化，并且其中任一数字不为0。
Figure A20078000995400121
R＝烷基，-O烷基，全氟烷基，任何取代的烷基-、芳基-、全氟芳基-，任何取代的芳基-，-(O-CH2CH2)n-OCH3
其他适合的基质材料是如下所述的侧链聚合物。
Figure A20078000995400131
R＝烷基，-O烷基，全氟烷基，任何取代的烷基-、芳基、全氟芳基-，任何取代的芳基-，-(O-CH2CH2)n-OCH3
[6，6]-苯基C-61-丁酸甲酯(PCBM)作为基质材料尤其适用。其经常作为电子传输组分用于有机太阳能电池中。
特别优选如下的掺杂剂
Figure A20078000995400141
其中X1、Y1是N或P，R0、R1-R16如权利要求2中对R的定义。
本发明另外的特征和优点在以下的实施例中阐明，以下的实施例不被认为以任何方式限制本发明的范围。
如果没有特别说明，使用自旋涂覆技术(基材处于室温，3000转每分钟)由溶液制备膜。溶液所有的操作都在手套操作箱中进行。在手套操作箱中进行膜的制备和操作。对于某些实验，则将膜转移到高真空室内。膜被沉积在玻璃基材上，所述玻璃基材配备有14mm长间隔为1.25mm的平行ITO触头。通过施加10V电压至平行ITO触头以进行电流测量。由电流、电压和样品的几何形状计算出导电率。
实施例1a(比较例)
105mg的聚[9，9-二辛基芴基-2，7-二基]-共-1，4-苯并-{2，1′-3}噻二唑)(YE)溶解在7ml甲苯中得到溶液。
Figure A20078000995400151
由溶液制备YE的薄膜。该膜没有显示任何电流(＜10-11A)。通过光学方法测得层厚为50nm。
第二步中，该膜被引入高真空中。将5nm的四(1，2，3，3a，4，5，6，6a，7，8-十氢-1，9，9b-三氮杂菲那烯基)二钨(II)(Ndop)蒸发到膜上。沉积后，电流增加了两个数量级到10-9A。这证明了Ndop具有将导电性引入YE的大体上充分的掺杂剂强度。
实施例1b(对比例)
105mg的聚[9，9-二辛基芴基-2，7-二基]-共-1，4-苯并-{2，1′-3}噻二唑)(YE)溶解于7ml甲苯中得到溶液。为制备YE和Ndop的混合物，将3mg的Ndop添加入2ml所述溶液中。
由该混合物经自旋涂覆技术浇铸薄膜。观察到电流小于10-11A的测限。根据实施例1a(比较例)，可以推断出尽管Ndop具有足够的掺杂强度，但并不能通过溶液处理而使YE被Ndop掺杂。
使数滴溶液在另一基材上干燥。发现得到的膜是不均匀的。其显示190pA的极小电流。
总之，对比例证明了含基质和施主部分的溶液在处理中遭遇的困难。
实施例2(本发明)
10mg聚[9，9-二辛基芴基-2，7-二基]-共-1，4-苯并-{2，1′-3}噻二唑)(YE)溶解于1ml甲苯中得到溶液。10c，10c’-双(8，9-二甲基-2，3，5，6-四氢-1H，4H-3a，6a，10b-三氮杂-荧蒽基)(二聚物)的溶液由10mg该二聚物溶解在1ml甲苯中而制备。YE：二聚物的混合溶液通过将1ml YE溶液和100μl二聚物溶液混合而制备。
通过自旋涂覆由该混合物浇铸薄膜。测得电流为180pA。通过光学方法测得层厚为50nm。该层相应的导电率为约3×10-7S/cm。
使一滴该混合溶液在另一基材上干燥。发现得到的膜是均匀的。开始它是透明黄色的。暴露于环境光一周后它显示出深棕色。这意味着发生了化学反应。暴露后它显示出180nA的电流。
实施例3(本发明)
将105mg聚[9，9-二辛基芴基-2，7-二基]-共-1，4-苯并-{2，1′-3}噻二唑)(YE)溶解于7ml甲苯中得到溶液。10c，10c’-双(8，9-二甲基-2，3，5，6-四氢-1H，4H-3a，6a，10b-三氮杂-荧蒽基)(二聚物)溶液由15mg二聚物溶解于1ml甲苯中而制备。YE：二聚物的混合溶液通过将1ml YE溶液和100μl二聚物溶液混合而制备。通过自旋涂覆由该混合溶液制备薄膜。所有步骤在受限的光照条件下进行。
受限光照条件的性能是防止蓝光和绿光在制备和操作期间到达溶剂和样品。这可以通过用具有RAL1028颜色的橙色透明箔遮盖操作区域来完成。将样品引入真空室。在没有绿光和蓝光的条件下，样品没有检测到导电性。最终，用白光直射样品。检测到2.1nA的电流，相应的导电率为4×10-6S/cm(测得层厚为50nm)。该实施例证明了使用本发明的掺杂剂能够避免薄膜处理中离子溶液遭遇的困难。YE在DCM中对Fc/Fc+的还原电位是-1.92V。因此，二聚物的氧化电位与YE的还原电位的能量差大于1eV。这确保了在没有足够能量的光存在的情况，掺杂剂前体不会发生活化。
实施例4(本发明)
如实施例3公开的同样条件制备膜。制备之后，将膜暴露在没有光的环境大气中10分钟。接下来，将该样品引入真空室内并暴露在白光下。暴露后测量电流为1.4nA。
该实施例证明在没有光的条件下膜甚至可以暴露在氧气和/或湿气中而对暴露于光后得到的导电性没有负作用。众所周之，传统n-型掺杂膜由于离子性物质对氧的高反应性因而会快速失去导电性。这样就允许例如在空气中通过溶液处理生产包括n-型掺杂电子传输层的OLED。这样可以促进生产，因为在印刷期间在大的基材上提供惰性气氛一直是一个问题。采用该方法可以涉及在环境气氛中印刷电子传输层，优选没有光的情况。在随后的步骤中，将该有机层引入真空中从而从有机层移除痕量的氧气和水，接着活化掺杂剂前体。
在前述的说明书和在权利要求中公开的特征，独自或者以其任意组合，是以其不同形式用于实现本发明的材料。

Claims (15)

1.用于制备掺杂的有机半导体材料的方法，其包含如下步骤：
(i)制备包含至少一种掺杂剂前体、至少一种待掺杂的有机材料和溶剂的溶液或悬浮液，
(ii)将所述溶液或悬浮液施用于基材上并移除溶剂，
(iii)通过施加活化能将掺杂剂前体转化为掺杂剂，其中所述掺杂剂前体是掺杂剂的二聚物、低聚物、聚合物、二螺化合物或多环，所述掺杂剂前体通过施加活化能解离为所述掺杂剂。
2.如权利要求1所述的制备掺杂的有机半导体材料的方法，其中所述掺杂剂选自：
Figure A2007800099540002C1
Figure A2007800099540003C1
其中结构3具有一个或多个环状键结A和/或A1和/或A2，其中A、A1和A2可以是碳环、杂环和/或多环体系，其可以被取代或未被取代；
其中结构5中A1和A2可单独或结合存在并且如上所限定，以及T＝CR22、CR22R23、N、NR21、O或S；
其中结构7具有一个或多个桥式键结Z和/或Z1和/或Z2，并且其中Z、Z1和Z2独立地选自烷基、烯基、炔基、环烷基、甲硅烷基、烷基甲硅烷基、重氮基、二硫基、杂环烷基、杂环基、哌嗪基、二烷基醚、聚醚、伯烷基胺、芳胺、多胺、芳基和杂芳基；
其中结构8a～8c中每个杂环的环尺寸可以在5～7个原子间改变；
其中X、Y＝O、S、N、NR21、P或PR21；R0-18、R21、R22和R23独立地选自取代或未取代的芳基、杂芳基、杂环基、二芳胺、二杂芳胺、二烷基胺、杂芳基烷基胺、芳基烷基胺、H、F、环烷基、卤代环烷基、杂环烷基、烷基、烯基、炔基、三烷基甲硅烷基、三芳基甲硅烷基、卤素、苯乙烯基、烷氧基、芳氧基、硫代烷氧基、硫代芳氧基、甲硅烷基和三烷基甲硅烷基炔基，或者其中R0-18、R21、R22和R23单独地或组合起来是(杂)脂族或(杂)芳族环体系的一部分。
3.如权利要求1或2所述的方法，其特征在于在步骤(iii)中的活化是经由光能、微波、超声、热能和/或电能实现的。
4.如前述任意权利要求所述的方法，其特征在于所述待掺杂的有机材料和所述掺杂剂前体在无电荷条件下使用。
5.如前述任意权利要求所述的方法，其特征在于在步骤(ii)中于基材上形成膜。
6.如权利要求5所述的方法，其特征在于所述膜通过旋涂、浸涂或印刷技术而制备，所述印刷技术例如喷墨印刷。
7.如前述任意权利要求所述的方法，其特征在于在步骤(iii)中所述掺杂剂前体不可逆地解离。
8.如前述任意权利要求所述的方法，其特征在于所述掺杂剂前体仅由类似于施主的部分组成，其在施加能量期间解离。
9.如前述任意权利要求所述的方法，其特征在于选择所述前体使得由其产生的n-掺杂剂相对于Fc/Fc+具有等于或小于-1.5V的氧化电位，优选相对于Fc/Fc+具有等于或小于-2.0V的氧化电位，更优选相对于Fc/Fc+具有等于或小于-2.2V的氧化电位。
10.如前述任意权利要求所述的方法，其特征在于所述溶剂选自四氯甲烷、苯、二氯甲烷、氯仿和四氢呋喃。
11.如前述任意权利要求所述的方法，其特征在于所述待掺杂的有机材料选自主族金属的喹啉络合物、酞菁络合物、卟啉络合物、菲咯啉、噁二唑、杂芳族化合物尤其是N-杂芳族化合物、及其混合物。
12.如前述任意权利要求所述的方法，其特征在于所述待掺杂的有机材料选自具有电荷传输功能的共轭聚合物、共聚物、低聚物或侧链聚合物。
13.如前述任意权利要求所述的方法，其特征在于所述基材选自柔性基材、玻璃基材、金属基材、聚合物膜、无机半导体。
14.如前述任意权利要求所述的方法，其特征在于步骤(i)和(ii)在排除掺杂剂前体转化为掺杂剂所必需的活化能的条件下进行。
15.一种配方物，其含有至少一种掺杂剂前体、至少一种待掺杂的有机材料、和溶剂，其中所述掺杂剂前体是掺杂剂的二聚物、低聚物、聚合物、二螺化合物或多环，所述掺杂剂前体通过施加活化能解离为所述掺杂剂。
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