CN101061089A - 水杨酸酯取代的共轭聚合物及器件 - Google Patents
水杨酸酯取代的共轭聚合物及器件 Download PDFInfo
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- CN101061089A CN101061089A CNA2005800400003A CN200580040000A CN101061089A CN 101061089 A CN101061089 A CN 101061089A CN A2005800400003 A CNA2005800400003 A CN A2005800400003A CN 200580040000 A CN200580040000 A CN 200580040000A CN 101061089 A CN101061089 A CN 101061089A
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- Prior art keywords
- alkyl
- polymkeric substance
- formula
- oxygen base
- aryl
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- 229960001860 salicylate Drugs 0.000 title description 6
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Abstract
一种化合物,其具有式(I)的结构单元。一种聚合物,其具有式(II)的结构单元。一种共轭聚合物,其具有一个或多个下式(III)的侧基。另外,由这些聚合物制备组合物、聚合物共混物、膜、涂层和电子器件。
Description
本申请要求2004年12月3日提交的临时申请即美国申请60/663,356的优先权,该临时申请通过引用结合到此。
发明背景
本申请涉及水杨酸酯取代的单体比如水杨酸酯取代的芴单体以及具有水杨酸酯侧基的共轭聚合物。本发明还涉及由这些聚合物制备的组合物、膜和涂层以及含有这些聚合物的电子器件。
人们已经发现含各种取代芴的聚合物在光电器件比如发光二极管、晶体管和光电池中非常有用,例如,参见美国专利6,605,373;6,593,450;6,514,632;6,512,083;6,383,664;6,353,083;6,309,763;6,255,449;6,255,447;6,204,515;6,169,163;5,962,631和5,708,130,这些专利中的每一个都通过引用将其全部结合到此。尽管某些共轭聚合物以及由其制备的器件取得了显著的成功,但是如果发现共轭聚合物提高了由其制备的器件的效率和寿命特性,则将是本领域中的更进一步的进展。
发明内容
本发明包括为由其制备的器件提供增加效率和延长寿命的特性的共轭聚合物。在一个实施方案中,本发明是含下式(III)的侧基的共轭聚合物,其中R1和R3相同或不同,并且各自独立地为H;其中一个或多个C和/或H可以被任意杂原子比如O、N、S、Si、P和F取代的烷基;芳烷基;芳基;取代芳基;杂芳基或取代杂芳基。R5为氢、C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基氧羰基、C1-20烃基羰基氧基、氰基或氟。
在另一个实施方案中,本发明是含下式(II)的结构单元的聚合物,其中R1、R2、R3、R4相同或不同,并且各自独立地为H;其中一个或多个C和/或H可以被任意杂原子比如O、N、S、Si、P和F取代的烷基;芳烷基;芳基;取代芳基;杂芳基或取代杂芳基;Y是共轭单元;R5和R6相同或不同,并且在每次出现时各自都独立地为氢、C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基氧羰基、C1-20烃基羰基氧基、氰基或氟;n是在大于等于0至小于等于0.999范围内的实数。
在另一个实施方案中,本发明是具有下式(I)的化合物,其中R1、R2、R3、R4相同或不同,并且各自独立地为H、其中一个或多个C和/或H可以被任意杂原子比如O、N、S、Si、P和F取代的烷基、芳烷基、芳基、取代芳基、杂芳基、取代杂芳基;X是任意的卤素、硼酸或硼酸酯;而R5和R6相同或不同,并且在每次出现时各自独立地为氢、C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基氧羰基、C1-20烃基羰基氧基、氰基或氟。
发明详述
在一个实施方案中,本发明是具有式(I)的化合物,其中R1、R2、R3、R4相同或不同,并且各自独立地为H、其中一个或多个C和/或H可以被任意杂原子比如O、N、S、Si、P和F取代的烷基、芳烷基、芳基、取代芳基、杂芳基、取代杂芳基;X是任意的卤素、硼酸或硼酸酯;而R5和R6相同或不同,并且在每次出现时各自独立地为氢、C1-20烃基、C1-20烃基氧基、硫醚、C1-20烃基氧羰基、C1-20烃基羰基氧基、氰基或氟。
式(I)
可以采用在上述被引专利中详述的过程制备具有式(I)的化合物。
在另一个实施方案中,本发明是含式(II)的结构单元的聚合物,其中R1、R2、R3、R4相同或不同,并且各自独立地为H、其中一个或多个C和/或H可以被任意杂原子比如O、N、S、Si、P和F取代的烷基、芳烷基、芳基、取代芳基、杂芳基、取代杂芳基;Y是任意共轭单元;R5和R6相同或不同,并且在每次出现时都各自独立地为氢、C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基氧羰基、C1-20烃基羰基氧基、氰基或氟;n是在大于等于0至小于等于0.999范围内的实数。
式(II)
在式(II)中,n可以是0,并且Y部分可以不存在。如果n不是0,则式(II)中的Y部分可以是下列部分中的一个或多个:
其中所述共轭单元可以带有取代基,这样的取代基在每次出现时都可以独立地为C1-20烃基、C1-20氢羧基氧基、C1-20硫醚、C1-20烃基氧羰基、C1-20氢羧基羰基氧基、氰基或氟基;
X1是O或S;
Q是R或Ar;
R是C1-40烃基或含一个或多个S、N、O、P或Si原子的C3-40烃基、氰基或氟;
Ar是C4至C40的芳基或杂芳基,或者是取代的C4至C40的芳基或杂芳基;
R’在每次出现时都独立地为H、C1-40烃基或含一个或多个S、N、O、P或Si原子的C3-40烃基,或者两个R’可以与芴上的9-碳一起形成可以含一个或多个S、N或O原子的C5-20环结构。
本发明的聚合物可以具有任意的拓扑结构,比如但不限于直链、支链、超支链(hyperbranched)的、均聚物、交替共聚物、无规共聚物、嵌段共聚物或接枝(grated)共聚物。
在另一个实施方案中,本发明是含式(III)的侧基的共轭聚合物,其中R1和R3相同或不同,并且各自独立地为H、其中一个或多个C和/或H可以被任意杂原子比如O、N、S、Si、P和F取代的烷基、芳烷基、芳基、取代芳基、杂芳基、取代杂芳基;R5为氢、C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基氧羰基、C1-20烃基羰基氧基、氰基或氟。
式(III)
本发明的聚合物可以通过用于制备芳族化合物的任何已知的偶合反应进行组装。优选地,使用Suzuki偶合反应。Suzuki反应采用二硼化芳族部分和二卤化芳族部分偶合芳族化合物。该反应可以形成长链、高分子量的聚合物。另外,通过控制加成的顺序,可以制备无规或嵌段共聚物。优选地,Suzuki反应采用二硼化单体开始。Suzuki法在美国专利5,777,070中有教导,特通过引用将该专利结合在此。
本发明的聚合物优选具有的重均分子量为约10,000道尔顿或更大、20,000道尔顿或更大或优选50,000道尔顿或更大;1,000,000道尔顿或更小、500,000道尔顿或更小或优选400,000道尔顿或更小。使用采用聚苯乙烯作为内标的凝胶渗透色谱确定分子量。
本发明的另一个实施方案涉及聚合物共混物。共混物包括与至少一个其它共轭聚合物共混的含式(II)重复单元的聚合物或含式(III)侧基的聚合物。如此处使用的,术语″共轭聚合物″表示具有重叠π轨道的骨架的聚合物。可以在共混物中使用的共轭聚合物包括聚芴、聚(亚芳基亚乙烯基)、聚亚苯基、聚茚并芴和聚噻酚,包括这些共轭聚合物中任一个的均聚物、共聚物或取代的均聚物和/或共聚物。
优选地,聚合物共混物由至少1重量%的含式II单元或含式III侧基的聚合物。优选地,共轭聚合物的带隙比含式II单元的聚合物的带隙窄。优选的聚合物共混物具有高的光致发光和电致发光效率。可以任选加入其它添加剂,比如粘度调节剂、抗氧化剂和涂层改进剂。另外,还可以配方形成具有两种或更多种组成类似但分子量不同的多分散性低的聚合物的共混物。优选地,聚合物表现出的多分散性(Mw/Mn)为10或更小,更优选5或更小,还更优选4或更小,最优选3或更小。
本发明的另一个实施方案是由本发明的聚合物形成的膜。这样的膜可以用于聚合物的发光二极管、光电池和场效应晶体管中。优选地,这样的膜用作发射层或载流子传输层。这些膜还可以用作电子器件用的保护膜以及用作荧光涂层。膜或涂层的厚度取决于用途。
通常地,这样的厚度可以为0.005至200微米。当涂层被用作荧光涂层时,涂层或膜的厚度为50至200微米。当涂层被用作电子保护层时,涂层的厚度可以为5至20微米。当涂层被用于聚合物发光二极管时,所形成层的厚度为0.005至0.2微米。本发明的聚合物形成无针孔且无缺陷的优良膜。
将聚合物组合物进行涂布易于形成膜,其中所述组合物含有聚合物和至少一种有机溶剂。优选的溶剂是脂肪族烃、氯代烃、芳族烃、酮、醚及它们的混合物。可以使用的其它溶剂包括1,2,4-三甲基苯、1,2,3,4-四甲基苯、戊基苯、1,3,5-三甲基苯、枯烯、甲基·异丙基苯、环己基苯、二乙苯、1,2,3,4-四氢化萘、十氢化萘、2,6-二甲基吡啶、2-氟-间-二甲苯、3-氟-邻-二甲苯、2-氯三氟甲苯、二甲基甲酰胺、2-氯-6-氟甲苯、2-氟苯甲醚、苯甲醚、2,3-二甲基吡嗪、4-氟苯甲醚、3-氟苯甲醚、3-三氟-甲基苯甲醚、2-甲基苯甲醚、苯乙醚、4-甲基苯甲醚、3-甲基苯甲醚、4-氟-3-甲基苯甲醚、2-氟苄腈、4-氟藜芦醚、2,6-二甲基苯甲醚、3-氟苄腈、2,5-二甲基苯甲醚、2,4-二甲基苯甲醚、苄腈、3,5-二甲基苯甲醚、N,N-二甲基苯胺、苯甲酸乙酯、1-氟-3,5-二甲氧基苯、1-甲基萘、N-甲基吡咯烷酮、3-氟三氟甲苯、三氟甲苯、三氟甲苯、二噁烷、三氟甲氧基苯、4-氟三氟甲苯、3-氟吡啶、甲苯、2-氟甲苯、2-氟三氟甲苯、3-氟甲苯、4-异丙基联苯、苯醚、吡啶、4-氟甲苯、2,5-二氟甲苯、1-氯-2,4-二氟苯、2-氟吡啶、3-氯氟苯、3-氯氟苯、1-氯-2,5-二氟苯、4-氯氟苯、氯苯、邻-二氯苯、2-氯氟苯、对-二甲苯、间-二甲苯、邻-二甲苯或邻-、间-和对-异构体的混合物。优选的是,这些溶剂具有较低的极性。高沸点溶剂(High boilers)和溶剂混合物较适用于喷墨,而二甲苯和甲苯最适用于旋涂。优选地,溶液包含约0.1至5%的含式I重复单元的聚合物。膜可以通过本领域中熟知的方式制备,这些方式包括旋涂、喷涂、浸涂、辊涂、胶版印刷、喷墨印刷、丝网印刷、印花涂布(stamp-coating)或刮刀法。
在另一个实施方案中,本发明是包含在溶剂中的本发明聚合物或聚合物共混物的组合物。可以使用的溶剂包括甲苯、二甲苯、二甲苯的邻、间和对-异构体的混合物、1,3,5-三甲基苯、二乙苯、乙苯或更高取代程度的苯衍生物。优选地,溶液含0.1至10重量%的组合物。对于薄涂层,优选溶液包含0.5至5.0重量%的组合物。通过适宜的方法将该组合物涂敷到合适的基底上,并且使溶剂蒸发。可以通过真空、热和/或通过用惰性气体比如氮吹扫,将残留溶剂除去。
除光致发光外,本发明的聚合物表现出强的电致发光。因此,本发明的另一个方面涉及有机电致发光(EL)器件,该器件具有含本发明聚合物的膜。相对于其中的电致发光聚合物膜不包含含三环胺的重复单元的器件,基于本发明聚合物的EL器件显示效率被提高。发明人的意思是将通常的三芳基胺部分和特别的三环胺结合到本发明的聚合物中,提高了EL器件的性能。优选地,当经受20伏或更小、10伏或更小或优选6伏或更小的施加电压时,本发明的EL器件发光。
有机EL器件通常由夹在阳极和阴极之间的有机膜构成。当将正偏压施加给器件时,空穴从阳极注入到有机膜中,而电子从阴极注入到有机膜中。空穴和电子的复合可以产生激子,而激子通过释放光子可以经历辐射衰变返回基态。
实际上,阳极为了其导电性和透明性而通常为锡和铟的混合氧化物。将混合氧化物(ITO)沉积在透明基底比如玻璃或塑料上,因而可以观察到有机膜发射的光。有机膜可以是各自为不同功能所设计的几个单独的层的复合体。由于空穴从阳极注入,因此与阳极相邻的层具有传输空穴的能力。类似地,与阴极相邻的层具有传输电子的能力。在很多情况下,电子或空穴传输层还可以作为发射层。在一些情况下,单层可以完成空穴及电子传输和发光的组合功能。
金属阴极可以通过热蒸发或溅射进行沉积。阴极的厚度可以为1nm至1000nm。优选的金属是钙、镁、铟、铝和钡。可以采用碱金属或碱土金属卤化物例如LiF、NaF、CsF或RbF的薄层(1-10nm)作为在发光聚合物和阴极即钙、钡或镁之间的缓冲层。还可以使用这些金属的合金。优选含1至5%锂的铝合金以及含至少80%镁的镁合金。
在优选实施方案中,电致发光器件包括至少一个空穴注入聚合物膜(例如,PEDOT膜)以及由本发明组合物构成且被安置在阳极材料和阴极材料之间的发光聚合物膜,使得当器件被施以正向偏压时,在所施加的电压下,空穴经由空穴注入聚合物膜从阳极材料注入发光聚合物中,而电子从阴极材料注入发光聚合物膜中,从而导致发光层发光。在另一个优选实施方案中,安置空穴传输聚合物的层,以使最靠近阳极的层具有最低的氧化电势,并且相邻层具有越来越高的氧化电势。通过这些方法,可以制备每单位电压具有较高光输出的电致发光器件。
″光电池″表示能够将入射光能量转变成电能的一类光电器件。光电池的实例是光生伏打器件、太阳能电池、光电二极管和光检测器。光电池通常包括沉积在透明基底上的透明或半透明第一电极。然后将聚合物膜形成到第一电极上,再涂上第二电极。传输穿过基底和第一电极的入射光被聚合物膜转变成激子,而激子在适当情况下能够离解成电子和空穴,因而产生电流。
本发明的另一个实施方案涉及金属-绝缘体-半导体场效应晶体管,该晶体管含有一种或多种用作半导体聚合物的本发明聚合物。场效应晶体管包括5个元件。第一元件是绝缘体层。该绝缘体层是电绝缘体,具有第一面和第二面。第二元件是栅极。栅极是电导体。栅极与所述绝缘体层的第一面相邻安置。
第三元件是半导体层。半导体层包括含上述式II结构单元的聚合物。半导体层具有第一面、第二面、第一末端和第二末端,半导体层的第二面与绝缘体层的第二面相邻。将聚合物沉积到绝缘体上,其中这些聚合物作为单层膜或作为多层膜存在,其组合厚度在10nm至1000nm的范围内、优选在25nm至500nm的范围内、最优选在50nm至300nm的范围内。
场效应晶体管的第四元件是源极。源极是电导体。源极与半导体层的第一末端电接触。第五元件是漏极。漏极是电导体。漏极与半导体层的第二末端电接触。施加给栅极的负偏压导致在连接源极与漏极的半导体层中形成空穴输送通道。施加给栅极的正偏压导致在所述半导体层中形成电子输送通道。
与电致发光器件一样,可以通过溶剂基处理技术比如旋涂、辊涂、浸涂、喷涂和刮涂和喷墨打印形成含半导体层的聚合物膜。当使用两种或更多种聚合物时,它们可以由含有所需聚合物的共混物的溶液分别沉积为不同的层或沉积为一个层。
将两个电极(源极和漏极)连接到半导电聚合物上,而将第三电极(栅极)连接到绝缘体的反面上。如果半导电聚合物是空穴传输(即,主要的载流子是正的空穴)的,则向栅电极施加负DC电压导致空穴累积在聚合物-绝缘体的界面附近,从而产生传导通道,电流通过该传导通道可以在源极和漏极之间流动。晶体管处于″开″状态。将栅极电压反转,使在累积区域内的空穴被耗尽,电流停止。晶体管处于″关″状态。
下列实施例详述了本发明的具体优选聚合物和比较例的制备,本发明的这些优选聚合物用于例如但不限于发光二极管器件。
下列实施例详述了具体优选化合物的制备。
实施例1
单体芴-二-水杨酸酯或2,7-二溴-9,9-二(4-己氧基-3-乙氧羰基苯基)芴(2)的合成(方案1)
方案1
将2,7-二溴-9-芴酮(20.28g,60mmol)、水杨酸乙酯(59.82g 360mmol)、巯基乙酸(0.55g,6mmol)和甲磺酸(250mL)在氮气和75℃下搅拌过夜。将混合物冷却到环境温度,然后逐步加入到具有冰/水的烧杯中。将所得混合物搅拌1小时。沉淀出橙色固体。该固体用热的乙腈洗涤。粗产物用丙酮重结晶,得到22.2g的产物(1),为浅橙色固体,该产物的纯度为约97%。用质子NMR确定结构。将3.26g的(1)(5mmol)、2.48g的1-溴己烷(15mmol)、3.46g的碳酸钾(25mmol)、0.4g的18-冠-6(1.5mmol)和35毫升的DMF加入到装备有电磁搅拌棒的圆底烧瓶中。该混合物在105℃搅拌过夜。将混合物冷却到环境温度,然后逐步加入到具有冰/水的烧杯中。将所得混合物搅拌1小时。沉淀出固体。该产物用EtOH重结晶,得到2.6g的2,7-二溴-9,9-二(4-己氧基-3-乙氧羰基苯基)芴(2),为浅黄色固体,纯度为约97%。采用质子NMR和质谱确定结构(2)。
比较例2(聚合物1)
聚合物1-发蓝光的聚合物的制备过程
向装备有顶上搅拌器和冷凝器的250mL三口烧瓶中,放入9,9-二辛基芴-2,7-硼酸乙二醇酯(99.9%,3.206g,6.038mmol)、2,7-二溴-9,9-二(4′-乙氧基乙氧苯基)芴(99.5%,2.940g,4.483mmol)、3,7-二溴-N-(4-正丁基苯基)-吩噁嗪(99.9%,0.7079g,1.494mmol)、甲苯(50mL)、相转移剂Aliquat336(0.87g)、反式-二氯二-(三苯膦)-钯(II)(4.2mg)和2M碳酸钠水溶液(13mL)。系统用氮气吹扫。混合物在105℃温和回流,直到观察到粘稠混合物为止。为了终止聚合,加入0.2g在THF中的苯基硼酸和10mL甲苯。混合物回流6小时。加入二乙基二硫代氨基甲酸钠三水合物的水溶液(DDC,3.5g在35mL水中)。混合物在约88℃及氮气下搅拌过夜。粘稠混合物被转移到分液漏斗中,将水层除去。有机相用2%的乙酸(水溶液)洗涤2次,并用温蒸馏水洗涤3次,经过使用甲苯作为洗脱剂的硅藻土/硅胶/碱性氧化铝柱。将稀聚合物溶液在旋转蒸发器上浓缩成2重量%的溶液。加入甲醇使聚合物沉淀,然后在55℃真空下干燥。在加热下,将粗聚合物重新溶解在甲苯(CMOS级)中,并且加入甲醇(CMOS级)进行第二次沉淀。将聚合物过滤,用甲醇(CMOS级)洗涤,并在55℃的真空烘箱中干燥。得到3.6克聚合物,该聚合物的Mw为570,000克/摩尔,多分散指数为2.9。
实施例3(聚合物2)
聚合物2-发蓝光聚合物的聚合过程
本实施例的这个过程类似于实施例2。下面列出的是用于聚合的单体及试剂:9,9-二辛基芴-2,7-硼酸乙二醇酯(99.9%,2.385g,4.491mmol)、2,7-二溴-9,9-二(4′-乙氧基乙氧苯基)芴(99.5%,1.094g,1.668mmol)、2,7-二溴-9,9-二(4-己氧基-3-乙氧羰基苯基)芴,2(99.5%,1.376g,1.668mmol)、3,7-二溴-N-(4-正丁基苯基)吩噁嗪(99.9%,0.527g,1.111mmol)、甲苯(40mL)、相转移剂Aliquat 336(0.66g)、反式-二氯二-(三苯膦)-钯(II)(3.1mg)和2M的碳酸钠水溶液(10mL)。得到2.9克聚合物,该聚合物的Mw为230,000克/摩尔,多分散指数为2.3。
实施例4(聚合物3)
聚合物3-发蓝光聚合物的聚合过程
本实施例的这个过程类似于实施例2。下面列出的是用于聚合的单体及试剂:9,9-二辛基芴-2,7-硼酸乙二醇酯(99.9%,2.442g,4.599mmol)、2,7-二溴-9,9-二(4′-乙氧基乙氧苯基)芴(99.6%,1.491g,2.277mmol)、2,7-二溴-9,9-二(4-己氧基-3-乙氧羰基苯基)芴,2(99.7%,0.937g,1.138mmol)、3,7-二溴-N-(4-正丁基苯基)吩噁嗪(99.9%,0.539g,1.138mmol)、甲苯(40mL)、相转移剂Aliquat 336(0.65g)、反式-二氯二-(三苯膦)-钯(II)(3.0mg)和2M的碳酸钠水溶液(10mL)。得到2.7克聚合物,该聚合物的Mw为290,000克/摩尔,多分散指数为2.3。
实施例5(聚合物4)
聚合物4-发蓝光聚合物的聚合过程
本实施例的这个过程类似于实施例2。下面列出的是用于聚合的单体及试剂:9,9-二辛基芴-2,7-硼酸乙二醇酯(99.9%,2.489g,4.689mmol)、2,7-二溴-9,9-二(4′-乙氧基乙氧苯基)芴(99.6%,1.824g,2.785mmol)、2,7-二溴-9,9-二(4-己氧基-3-乙氧羰基苯基)芴,2(99.7%,0.573g,0.696mmol)、3,7-二溴-N-(4-正丁基苯基)-吩噁嗪(99.9%,0.550g,1.161mmol)、甲苯(40mL)、相转移剂Aliquat 336(0.68g)、反式-二氯二-(三苯膦)-钯(II)(3.6mg)和2M的碳酸钠水溶液(10mL)。得到2.9克聚合物,该聚合物的Mw为339,000克/摩尔,多分散指数为2.5。
实施例6(聚合物5)
聚合物5-发蓝光聚合物的聚合过程
向装备有顶上搅拌器和冷凝器的250mL三口烧瓶中,放入9,9-二辛基芴-2,7-硼酸乙二醇酯(F8-BE)(99.9%,2.229g,4.197mmol)、2,7-二溴-9,9-二(4-己氧基-3-乙氧羰基苯基)芴(BSAFBr2)(99.7%,2.565g,3.117mmol)、3,7-二溴-N-(4-正丁基苯基)吩噁嗪(POZBr2)(99.9%,0.492g,1.039mmol)、甲苯(40mL)、相转移剂Aliquat 336(0.60g)、反式-二氯二(三苯膦)-钯(II)(2.9mg)和2M的碳酸钠水溶液(9mL)。系统用氮气吹扫。将混合物温和回流(105℃)~2.5小时,直到观察到粘稠混合物为止。为了终止聚合,加入0.2g在THF中的苯基硼酸和10mL甲苯。混合物回流5小时。加入二乙基二硫代氨基甲酸钠三水合物的水溶液(DDC,3.5g在35mL水中)。混合物在~88℃及氮气下搅拌过夜。混合物被转移到分液漏斗中,将水层除去。有机相用2%的乙酸(水溶液)和温蒸馏水洗涤,经过硅藻土/硅胶/碱性氧化铝柱,并用甲苯洗脱。将稀聚合物溶液在旋转蒸发器上浓缩成~1-2重量%的溶液。用甲醇使聚合物沉淀,并在55℃真空下干燥。在加热下,将粗聚合物重新溶解在甲苯(CMOS级)中,并且用甲醇(CMOS级)进行第二次沉淀。将聚合物过滤,用甲醇(CMOS级)洗涤,并在55℃的真空烘箱中干燥。得到2.8克聚合物:Mw=370,000;PDI(多分散指数)=2.2。DSC测量显示这种聚合物是玻璃化转变温度(Tg)为135℃的无定形聚合物。
聚合物1-5在发光二极管器件中的比较
聚合物 | 光效率(Cd/A)@200cd/m2 | 光效率(Cd/A)@1000cd/m2 | 光效率(Cd/A)@4000cd/m2 | 光效率(Cd/A)@10000cd/m2 | 最大亮度(Cd/m2) | 色坐标CIE(1931)(X,Y) | AC寿命(小时) |
聚合物1 | 3.55 | 4.39 | 4.87 | 4.84 | 13489 | 0.15,0.26 | 396 |
聚合物2 | 3.14 | 3.81 | 4.01 | 3.85 | 9241 | 0.17,0.27 | 472 |
聚合物3 | 3.68 | 4.33 | 4.60 | 4.37 | 10992 | 0.15,0.26 | 469 |
聚合物4 | 3.71 | 4.45 | 4.79 | 4.70 | 13018 | 0.15,0.25 | 439 |
聚合物5 | 4.4 | 4.5 | 4.1 | N/A | 4404 | 0.15,0.27 | 508 |
上表中的数据表明,相比于现有技术的聚合物(聚合物1),由本发明聚合物(聚合物2-4)制备的器件的寿命得到了显著的提高。因此,在不希望受理论束缚的情况下,申请人认为,本发明的水杨酸酯基与在阳离子态的阴极金属配位,使得来自阴极的电子注入得到提高,因此,促进器件的效率及寿命得到令人惊奇的改善。
结论
尽管本发明已经作为优选方面进行了描述,但是本发明可以在此公开内容的精神和范围内进一步改进。因此,本申请欲采用此处公开的通则涵盖本发明所有的变化、用途或适应性。此外,本申请欲涵盖这些与本发明公开内容有偏离但来自本发明所从属的领域内的已知或通常实践中并且落入后附的权利要求的限制内的情况。
Claims (20)
1.一种化合物,其包含式(I)的结构单元:
式(I)
其中R1、R2、R3、R4相同或不同,并且各自独立地为H、其中一个或多个C和/或H可以被O、N、S、Si、P和F中至少一个取代的烷基、芳烷基、芳基、取代芳基、杂芳基、取代杂芳基;X是卤素、硼酸或硼酸酯;而R5和R6相同或不同,并且在每次出现时各自独立地为氢、C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基氧羰基、C1-20烃基羰基氧基、氰基或氟。
4.权利要求2的聚合物,其中n为0。
5.权利要求2的聚合物,其中Y为下面中的一个或多个:
其中所述共轭单元可以带有取代基,取代基在每次出现时可以独立地为C1-20烃基、C1-20氢羧基氧基、C1-20硫醚、C1-20烃基氧羰基、C1-20氢羧基羰基氧基、氰基或氟基;
X1是O或S;
Q是R或Ar;
R是C1-40烃基或含一个或多个S、N、O、P或Si原子的C3-40烃基、氰基或氟;
Ar是C4至C40的芳基或杂芳基,或者是取代的C4至C40的芳基或杂芳基;
R’在每次出现时独立地为H、C1-40烃基或含一个或多个S、N、O、P或Si原子的C3-40烃基,或者两个R’可以与芴上的9-碳一起形成可以含一个或多个S、N或O原子的C5-20环结构。
6.一种组合物,其含有权利要求2的聚合物。
7.一种组合物,其含有权利要求3的聚合物。
8.一种电子器件,其包含含权利要求2的聚合物的膜或涂层。
9.一种电子器件,其包含含权利要求3的聚合物的膜或涂层。
11.权利要求2的聚合物,其中所述聚合物是共轭或部分共轭的。
12.权利要求3的聚合物,其中所述聚合物是共轭或部分共轭的。
13.权利要求2的聚合物,其中所述聚合物是直链、支链、超支链的、均聚物、交替共聚物、无规共聚物、嵌段共聚物或接枝共聚物。
14.权利要求3的聚合物,其中所述聚合物是直链、支链、超支链的、均聚物、交替共聚物、无规共聚物、嵌段共聚物或接枝共聚物。
15.权利要求6的组合物,进一步包括溶剂、低聚物或聚合物。
16.权利要求7的组合物,进一步包括溶剂、低聚物或聚合物。
17.一种聚合物共混物,其包括权利要求2的聚合物。
18.一种聚合物共混物,其包括权利要求3的聚合物。
19.一种膜,其包括权利要求2的聚合物。
20.一种膜,其包括权利要求3的聚合物。
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JP5144938B2 (ja) | 2007-02-02 | 2013-02-13 | 住友化学株式会社 | 高分子発光素子、高分子化合物、組成物、液状組成物及び導電性薄膜 |
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US9780308B2 (en) | 2009-12-25 | 2017-10-03 | Sumitomo Chemical Company, Limited | Composition and light emitting device using the same |
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WO2006060437A3 (en) | 2006-11-09 |
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CN101838387A (zh) | 2010-09-22 |
DE112005003032T5 (de) | 2007-12-13 |
CN101061089B (zh) | 2011-07-27 |
US20090001324A1 (en) | 2009-01-01 |
WO2006060437A2 (en) | 2006-06-08 |
TWI365200B (en) | 2012-06-01 |
GB2436758B (en) | 2009-10-21 |
CN101838387B (zh) | 2012-02-29 |
KR101240694B1 (ko) | 2013-03-07 |
GB2436758A (en) | 2007-10-03 |
GB0712285D0 (en) | 2007-08-01 |
US8052894B2 (en) | 2011-11-08 |
JP5457634B2 (ja) | 2014-04-02 |
KR20070089928A (ko) | 2007-09-04 |
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