CN105793387A - 含有包含丙烯酸酯和/或甲基丙烯酸酯单元的聚合物粘结剂的组合物 - Google Patents
含有包含丙烯酸酯和/或甲基丙烯酸酯单元的聚合物粘结剂的组合物 Download PDFInfo
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- CN105793387A CN105793387A CN201480065940.7A CN201480065940A CN105793387A CN 105793387 A CN105793387 A CN 105793387A CN 201480065940 A CN201480065940 A CN 201480065940A CN 105793387 A CN105793387 A CN 105793387A
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- 239000011230 binding agent Substances 0.000 title abstract description 27
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- 125000005397 methacrylic acid ester group Chemical group 0.000 title abstract 2
- 239000000463 material Substances 0.000 claims abstract description 78
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
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- 125000003118 aryl group Chemical group 0.000 claims description 17
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Abstract
本发明涉及包含有机发光材料和/或电荷传输材料以及包含丙烯酸酯和/或甲基丙烯酸酯单元的聚合物粘结剂的新型组合物,涉及其作为用于制备有机发光二极管(OLED)器件的导电油墨的用途,涉及使用所述新型制剂制备OLED器件的方法,以及涉及由这样的方法和制剂制备的OLED器件。
Description
技术领域
本发明涉及包含有机发光材料和/或电荷传输材料以及包含丙烯酸酯和/或甲基丙烯酸酯单元的聚合物粘结剂(polymericbinder)的新型组合物,涉及其作为用于制备有机发光二极管(OLED)器件的油墨的用途,涉及使用所述新型组合物制备OLED器件的方法,以及涉及由这样的方法和组合物制备的OLED器件。
背景技术
当制备OLED器件时,通常使用印刷技术如喷墨印刷、卷对卷印刷、狭缝式染料涂布(slotdyecoating)、柔性版印刷或凹版印刷来施加活性层。基于大部分可用作发光材料和/或电荷传输材料的有机化合物的低溶解度,这些技术需要使用大量的溶剂。
为了改进成膜能力,可以使用粘合剂(bindingagent)。对于具有小分子量的发光材料和/或电荷传输材料或者具有低分子量的聚合物化合物来说,尤其需要这些添加剂。
EP1883124A1描述了特别适合通过印刷技术形成显示器和灯的发光材料的制剂,所述制剂包含容纳在保护性多孔基质材料中的有机发光材料,粘结剂和溶剂。然而,OLED材料也包含聚合物材料。此外,粘结剂材料作为不具有任何详细说明的长列表公开。
US2007/0103059A1公开了包含OLED材料和具有非常特定的重复单元的聚合物的组合物。添加所述具有特定重复单元的聚合物以提高OLED的发光效率。还可以使用聚合物OLED材料。
根据US6,818,919B1和US7,115,430B1,必须使用具有高玻璃化转变温度Tg的聚合物以加工低分子量有机发光和电荷传输材料。然而,这些材料是昂贵的并且限制组合物的应用。
US5,952,778B1涉及具有改进的保护罩的封装有机发光器件,所述保护罩包含钝化金属的第一层、无机介电材料的第二层和聚合物的第三层。有机发光材料可以是聚合的或单体的。组合物可含有聚合物粘结剂。然而,所述粘结剂材料以不具有任何详细说明的长列表公开。
US6,277,504B1公开了特定发光化合物和包含其的组合物。所述组合物可包括粘结剂。然而,未提供所述粘结剂的详细说明。
US6,294,273B1描述了可溶于甲醇中的发光化合物。包含这些化合物的组合物可含有聚合物粘结剂。然而,所述粘结剂材料以不具有任何详细说明的长列表公开。
WO2005/055248A2涉及包含特定有机半导体化合物和在1000Hz下具有3.3或更小的介电常数的有机粘结剂的组合物。然而,如WO2005/055248A2中所公开的特定有机半导体化合物应该形成具有高结晶度的层以达到高效率。与此相反,发光层通常应该具有低结晶度以提供高效率。因此,WO2005/055248A2的理念不能应用于OLED层。
小分子在溶剂中的溶液通常不会像聚合物情况下发生的一样对所得溶液的粘度具有很大影响。因此,用于常规印刷应用如喷墨印刷、柔性版或凹版印刷的小分子的组合物需要添加剂来增加油墨粘度并改进成膜性。现有技术提供可用于加工低分子量有机发光和电荷传输材料的组合物。然而,永久希望改进OLED层的性能,特别是在效率、寿命和关于氧化和/或水的敏感性方面改进。
因此希望具有包含适合通过前述的溶液系方法制备OLED器件的发光材料和/或电荷传输材料的流体,所述流体允许制造具有高效率、长寿命和针对水和/或氧化的低敏感性的非常均匀的OLED器件。本发明的一个目的是提供这样的改进流体。另一个目的是提供从这样的流体制备OLED器件的改进方法。另一个目的是提供从这样的流体和方法获得的改进的OLED器件。根据以下描述,其它目的对本领域技术人员是立即显而易见的。
令人惊讶的是,已发现,通过提供如本发明中所要求保护的方法、材料和器件,特别是通过提供使用含有包含丙烯酸酯和/或甲基丙烯酸酯单元的聚合物粘结剂的组合物来制备OLED器件的方法,能够实现这些目的,并且能够解决上述问题。
发明内容
本发明涉及一种组合物,所述组合物包含一种或多种具有至多5000g/摩尔的分子量的有机发光材料和/或电荷传输材料、一种或多种有机溶剂和一种或多种聚合物,其特征在于所述聚合物包含丙烯酸酯和/或甲基丙烯酸酯单元。
本发明还涉及如上文和下文所述的也经常称作制剂的组合物作为用于制备OLED器件、特别是用于刚性和柔性OLED器件的涂料或印刷油墨的用途。
本发明还涉及一种制备有机发光二极管(OLED)器件的方法,所述方法包括如下步骤:
a)将如上文和下文所述的组合物沉积在基底上,优选地形成膜或层,和
b)例如通过蒸发除去一种或多种溶剂。
本发明还涉及一种从如上文和下文所述的组合物和/或通过如上文和下文所述的方法制备的OLED器件。
OLED器件可以例如用于照明,用于医疗照明目的,用作信号装置,用作标志装置,和用在显示器中。可以使用无源矩阵驱动、总矩阵寻址或有源矩阵驱动来对显示器寻址。可以通过使用光学透明电极来制造透明OLED。可通过柔性基底的使用来获得(assessable)柔性OLED。
本发明的组合物、方法和器件提供OLED器件和其生产的效率的令人惊讶的改进。出乎意料的是,如果通过使用本发明的组合物实现OLED器件,则这些器件的性能、寿命和效率能够得到改进。此外,本发明的组合物提供非常惊人的高成膜水平。特别是,膜的均匀性和品质能够得到改进。除此之外,本发明能够实现多层器件的更好溶液印刷。
具体实施方式
所述有机发光材料和/或电荷传输材料可以选自本领域技术人员已知以及在文献中描述的具有至多5000g/摩尔的分子量的标准材料。优选地,所述组合物包含有机发光材料。根据本申请的有机发光材料是指具有在300至800nm范围内的λ最大的发光材料。
根据本发明的组合物优选包含0.01重量%和20重量%之间、更优选0.2重量%和10重量%之间,最优选0.25重量%和5重量%之间的所述有机发光材料和/或电荷传输材料或相应的掺合物。百分比数据涉及100%的溶剂或溶剂混合物。
在此使用的发光材料或电荷传输材料(下文合称为有机半导体)是纯组分或两种或更多种组分的混合物。所述有机发光材料和/或电荷传输材料优选包括磷光化合物。
合适的磷光化合物特别是如下的化合物,所述化合物在适当激发时发光,优选在可见区发光,并且另外含有至少一个原子序数大于20、优选大于38且小于84、更优选大于56且小于80的原子。使用的磷光发光体优选是含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,特别是含有铱或铂的化合物。
特别优选的有机磷光化合物是式(1)至(4)的化合物:
其中
DCy在每次出现时相同或不同地是含有至少一个供体原子,优选地氮、呈碳烯形式的碳或磷的环状基团,所述环状基团通过所述供体原子键合至金属,并且所述环状基团又可带有一个或多个取代基R1;所述基团DCy和CCy通过共价键彼此连接;
CCy在每次出现时相同或不同地是含有碳原子的环状基团,所述环状基团通过所述碳原子键合至金属并且所述环状基团又可带有一个或多个取代基R1;
A在每次出现时相同或不同地是单阴离子二齿螯合配体,优选地是二酮配体;
R1在每种情况下相同或不同并且是F,Cl,Br,I,NO2,CN,具有1至20个碳原子的直链、支链或环状的烷基或烷氧基基团,其中一个或多个非相邻的CH2基团可被-O-、-S-、-NR2-、-CONR2-、-CO-O-、-C=O-、-CH=CH-或-C≡C-代替,并且其中一个或多个氢原子可被F代替,或者具有4至14个碳原子并且可被一个或多个非芳族R1基团取代的芳基或杂芳基基团,并且多个在同一环上或在两个不同环上的取代基R1又可一起形成单环或多环的脂族或芳族环系;并且
R2在每种情况下相同或不同并且是具有1至20个碳原子的直链、支链或环状的烷基或烷氧基基团,其中一个或多个非相邻的CH2基团可被-O-、-S-、-CO-O-、-C=O-、-CH=CH-或-C≡C-代替,并且其中一个或多个氢原子可被F代替,或者具有4至14个碳原子并且可被一个或多个非芳族R1基团取代的芳基或杂芳基基团。
多个基团R1之间形成环系是指在基团DCy与CCy之间也可存在桥连基。此外,多个基团R1之间形成环系是指在两个或三个配体CCy-DCy之间或在一个或两个配体CCy-DCy与配体A之间也可存在桥连基,得到多齿或多足配体体系。
申请WO00/70655、WO01/41512、WO02/02714、WO02/15645、EP1191613、EP1191612、EP1191614、WO04/081017、WO05/033244、WO05/042550、WO05/113563、WO06/008069、WO06/061182、WO06/081973和DE102008027005揭示了上述发光体的实例。一般来说,根据现有技术用于磷光OLED的和在有机电致发光领域中的本领域技术人员所知的所有磷光络合物都是合适的,并且本领域技术人员将能够在无需创造性劳动的情况下使用其它磷光化合物。特别是,本领域技术人员已知何种磷光络合物以何种发光颜色发光。
优选磷光化合物的实例示于下表中。
优选的掺杂剂选自如下类别:单苯乙烯基胺、二苯乙烯基胺、三苯乙烯基胺、四苯乙烯基胺、苯乙烯基膦、苯乙烯基醚和芳基胺。单苯乙烯基胺被认为是指含有一个取代或未取代的苯乙烯基基团和至少一个胺、优选芳族胺的化合物。二苯乙烯基胺被认为是指含有两个取代或未取代的苯乙烯基基团和至少一个胺、优选芳族胺的化合物。三苯乙烯基胺被认为是指含有三个取代或未取代的苯乙烯基基团和至少一个胺、优选芳族胺的化合物。四苯乙烯基胺被认为是指含有四个取代或未取代的苯乙烯基基团和至少一个胺、优选芳族胺的化合物。所述苯乙烯基基团特别优选是还可被进一步取代的茋。与所述胺类似地定义相应的膦和醚。为了本发明的目的,芳基胺或芳族胺被认为是指含有与氮直接键合的三个取代或未取代的芳族或杂芳族环系的化合物。这些芳族或杂芳族环系中的至少一个优选是稠合环系,特别优选地具有至少14个芳族环原子的稠合环系。其优选的实例是芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族胺或芳族二胺。芳族蒽胺被认为是指其中一个二芳基氨基基团直接与蒽基团优选在9位键合的化合物。芳族蒽二胺被认为是指其中两个二芳基氨基基团直接与蒽基团优选在9,10位键合的化合物。与此类似地定义芳族的芘胺、芘二胺、胺和二胺,其中所述二芳基氨基基团优选与芘在1位或在1,6位键合。其它优选的掺杂剂选自茚并芴胺或茚并芴二胺,例如根据WO06/122630的,苯并茚并芴胺或苯并茚并芴二胺,例如根据WO08/006449的,和二苯并茚并芴胺或二苯并茚并芴二胺,例如根据WO07/140847的。来自苯乙烯基胺类别的掺杂剂的实例是取代或未取代的三茋胺或在WO06/000388、WO06/058737、WO06/000389、WO07/065549和WO07/115610中描述的掺杂剂。此外优选在DE102008035413中公开的稠合烃。
此外,合适的掺杂剂是下表中描绘的结构,和在JP06/001973、WO04/047499、WO06/098080、WO07/065678、US2005/0260442和WO04/092111中公开的这些结构的衍生物。
另一组掺杂剂是短(低聚-)亚芳基亚乙烯基(例如根据EP676461的DPVBi或螺-DPVBi)。
发光层混合物中的掺杂剂的比例优选是0.1重量%和50.0重量%之间,更优选是0.5重量%和20.0重量%之间,最优选是1.0重量%和10.0重量%之间。相应地,主体材料的比例优选是50.0重量%和99.9重量%之间,更优选是80.0重量%和99.5重量%之间,最优选是90.0重量%和99.0重量%之间。
适用于这个目的的主体材料是来自各种物质类别的材料。优选的主体材料选自如下的类别:低聚亚芳基(例如根据EP676461的2,2',7,7'-四苯基螺二芴,或二萘基蒽),特别是含有稠合芳族基团的低聚亚芳基,低聚亚芳基亚乙烯基,多足金属络合物(例如根据WO04/081017),空穴传导化合物(例如根据WO04/058911),电子传导化合物,特别是酮、氧化膦、亚砜等(例如根据WO05/084081和WO05/084082),阻转异构体(例如根据WO06/048268),硼酸衍生物(例如根据WO06/117052),苯并蒽(例如根据WO08/145239),三嗪或苯并咪唑。此外,合适的主体材料也是上述的根据本发明的苯并[c]菲化合物。除了根据本发明的化合物之外,特别优选的主体材料选自如下的类别:含有萘、蒽、苯并蒽和/或芘或这些化合物的阻转异构体的低聚亚芳基,低聚亚芳基亚乙烯基,酮,氧化膦和亚砜。除了根据本发明的苯并[c]菲化合物之外,非常特别优选的主体材料选自如下的类别:含有蒽、苯并蒽和/或芘或这些化合物的阻转异构体的低聚亚芳基。为了本发明的目的,低聚亚芳基旨在被认为是指其中至少三个芳基或亚芳基基团彼此键合的化合物。
此外,合适的主体材料例如是下表中描绘的材料,和如WO04/018587、WO08/006449、US5935721、US2005/0181232、JP2000/273056、EP681019、US2004/0247937和US2005/0211958中所公开的这些材料的衍生物。
为了本发明的目的,空穴注入层是与阳极直接相邻的层。为了本发明的目的,空穴传输层是位于空穴注入层与发光层之间的层。它们可优选用电子受体化合物、例如用F4-TCNQ或用如在EP1476881或EP1596445中所述的化合物进行掺杂。
除了根据本发明的材料之外,如可用于根据本发明的有机电致发光器件的空穴注入或空穴传输层中或电子注入或电子传输层中的合适的电荷传输材料例如是Y.Shirota等,Chem.Rev.(化学评论)2007,107(4),953-1010中所公开的化合物,或根据现有技术用于这些层中的其它材料。
可用于根据本发明的电致发光器件的空穴传输或空穴注入层中的优选的空穴传输材料的实例是茚并芴胺和衍生物(例如根据WO06/122630或WO06/100896)、如EP1661888中公开的胺衍生物、六氮杂苯并菲衍生物(例如根据WO01/049806)、具有稠合芳族化合物的胺衍生物(例如根据US5,061,569)、如WO95/09147中公开的胺衍生物、单苯并茚并芴胺(例如根据WO08/006449)或二苯并茚并芴胺(例如根据WO07/140847)。此外,合适的空穴传输和空穴注入材料是上述化合物的衍生物,如JP2001/226331、EP676461、EP650955、WO01/049806、US4780536、WO98/30071、EP891121、EP1661888、JP2006/253445、EP650955、WO06/073054和US5061569中所公开的。
此外,合适的空穴传输或空穴注入材料例如是下表中所示的材料。
可用于根据本发明的电致发光器件中的合适的电子传输或电子注入材料例如是下表中所示的材料。此外,合适的电子传输和电子注入材料是上述化合物的衍生物,如JP2000/053957、WO03/060956、WO04/028217和WO04/080975中所公开的。
对于根据本发明的化合物,合适的基质材料是酮、氧化膦、亚砜和砜,例如根据WO04/013080、WO04/093207、WO06/005627或DE102008033943的,三芳基胺,咔唑衍生物,例如CBP(N,N-双咔唑基联苯)或公开在WO05/039246、US2005/0069729、JP2004/288381、EP1205527或WO08/086851中的咔唑衍生物,吲哚并咔唑衍生物,例如根据WO07/063754或WO08/056746的,氮杂咔唑,例如根据EP1617710、EP1617711、EP1731584、JP2005/347160的,双极性基质材料,例如根据WO07/137725的,硅烷,例如根据WO05/111172的,氮杂硼杂环戊二烯或硼酸酯,例如根据WO06/117052的,三嗪衍生物,例如根据DE102008036982、WO07/063754或WO08/056746的,或锌络合物,例如根据DE102007053771的。
关于另外的优选,可以使用具有并三苯(triacene)结构、例如蒽和菲结构的电荷传输材料。并三苯结构是指具有正好三个稠合芳族环的稠合芳族烃结构。关于本发明的这个实施方式,并三苯结构不包括并四苯或并五苯结构。
所述发光材料和/或电荷传输材料具有至多5000g/摩尔、优选地至多2000g/摩尔、更优选地至多1500g/摩尔、最优选地至多1000g/摩尔的分子量。
根据本发明的一个特别实施方式,所述组合物优选包含0.01重量%至20重量%、更优选地0.2重量%至10重量%、最优选地0.25重量%至5重量%的发光材料和/或电荷传输材料。
此外,本发明的组合物包含至少一种包含丙烯酸酯和/或甲基丙烯酸酯单元的聚合物。所述聚合物可用作惰性粘结剂。这意味着,所述聚合物不具有半导性质或不与组合物中的半导体化合物中的任一种化学地反应。如上文和下文所用的术语“化学地反应”是指所述非导电添加剂与有机发光材料和/或电荷传输材料在用于制剂和OLED器件的制造、储存、运输和/或使用的条件下可能的氧化或其它化学反应。
所述聚合物包含5摩尔%至100摩尔%、优选地25摩尔%至100摩尔%、更优选地50摩尔%至100摩尔%、最优选地100摩尔%的选自丙烯酸酯和/或甲基丙烯酸酯单元的重复单元。
在第一优选实施方式中,所述聚合物包含5摩尔%至100摩尔%、优选地25摩尔%至100摩尔%、更优选地50摩尔%至100摩尔%、最优选地100摩尔%的选自甲基丙烯酸酯单元的重复单元。
在第二优选实施方式中,所述聚合物包含5摩尔%至100摩尔%、优选地25摩尔%至100摩尔%、更优选地50摩尔%至100摩尔%、最优选地100摩尔%的选自丙烯酸酯单元的重复单元。
在第三优选实施方式中,所述聚合物包含5摩尔%至100摩尔%、优选地25摩尔%至100摩尔%、更优选地50摩尔%至100摩尔%、最优选地100摩尔%的选自丙烯酸酯单元和甲基丙烯酸酯单元的重复单元。
可以使用现有技术中已知的所有单元作为甲基丙烯酸酯单元。优选的是具有C1-10烷基基团、C3-8环烷基基团、C6-14芳基基团或C2-13杂芳基基团作为酯基团的甲基丙烯酸酯单元。更优选的是具有甲基、乙基、正丁基、异丁基、叔丁基、环己基、异冰片基、苄基或缩水甘油基(glycidly)基团作为酯基团的甲基丙烯酸酯单元。
可以使用现有技术中已知的所有单元作为丙烯酸酯单元。优选的是具有C1-10烷基基团、C3-8环烷基基团、C6-14芳基基团或C2-13杂芳基基团作为酯基团的丙烯酸酯单元。更优选的是具有甲基或乙基基团作为酯基团的丙烯酸酯单元。
除了所述丙烯酸酯和/或甲基丙烯酸酯单元之外,所述聚合物可以包含其它的重复单元。所述聚合物包含0摩尔%至95摩尔%、优选地0摩尔%至75摩尔%、更优选地0摩尔%至50摩尔%的另外的重复单元。
不同于所述丙烯酸酯单元和甲基丙烯酸酯单元的另外的重复单元可以选自现有技术中已知作为丙烯酸酯和/或甲基丙烯酸酯单元的共聚单元(co-unit)的所有单元。
优选作为另外的重复单元的是选自如下的单元:苯乙烯,在侧链中被烷基取代基取代的苯乙烯如α-甲基苯乙烯和α-乙基苯乙烯,在环上被烷基取代基取代的苯乙烯如乙烯基甲苯和对甲基苯乙烯,被卤素原子取代的苯乙烯如单氯苯乙烯、二氯苯乙烯、三溴苯乙烯和四溴苯乙烯,烯烃如乙烯、丙烯、丁烯、异戊二烯和1,3-丁二烯,丙烯腈和马来酸酐。
优选地,所述聚合物包含在500,000g/摩尔至50,000,000g/摩尔、更优选750,000g/摩尔至5,000,000g/摩尔、最优选1,000,000g/摩尔至3,000,000g/摩尔范围内的重均分子量。利用具有至少500,000g/摩尔、更优选地至少1,000,000g/摩尔的重均分子量的聚合物可以实现令人惊讶的效果。
在本发明的一个特别优选的实施方式中,所述聚合物是具有优选地在750,000g/摩尔至5,000,000g/摩尔范围内、更优选地在1,000,000g/摩尔至3,000,000g/摩尔范围内的重均分子量的聚甲基丙烯酸甲酯均聚物。
优选地,所述聚合物具有在1.0至10.0范围内、更优选地在1.0至4.0范围内、最优选地在1.05至3的范围内的多分散指数Mw/Mn。
通常,所述聚合物可分散或可溶在如上文和下文所述的本发明组合物的溶剂中。优选地,所述聚合物可溶在有机溶剂中,并且所述聚合物在溶剂中的溶解度是至少1g/l,更优选是至少5g/l,最优选是至少10g/l。
根据本发明的一个特别实施方式,所述组合物可以包含在优选地0.1重量%至80重量%、更优选地1重量%至50重量%、最优选地5重量%至40重量%的一种或多种固体化合物的范围内的总固体。
所述一种或多种聚合物相对于组合物内的所述发光材料和/或电荷传输材料的重量比优选在1:1000至4:1范围内,更优选在1:100至1:1范围内,最优选在1:20至2:3范围内。
有用且优选的聚合物包含如下的汉森溶解度参数:在14.5至23.0MPa0.5范围内的Hd,在0.0至20.0MPa0.5范围内的Hp和在0.0至15.5MPa0.5范围内的Hh。更优选的聚合物粘结剂包含如下的汉森溶解度参数:在15.0至21.0MPa0.5范围内的Hd,在1.0至8.0MPa0.5范围内的Hp和在5.0至15.0MPa0.5范围内的Hh。最优选的聚合物粘结剂包含如下的汉森溶解度参数:在16.0至20.0MPa0.5范围内的Hd,在3.0至5.0MPa0.5范围内的Hp和在5至12.0MPa0.5范围内的Hh。
可以根据如由Hanson和Abbot等提供的Practice(HSPiP)程序(第2版)中的汉森溶解度参数来确定所述汉森溶解度参数。
有用的聚合物的实例公开于表1中。
表1:有用的聚合物粘结剂的汉森溶解度参数
Hd是指分散性贡献
Hp是指极性贡献
Hh是指氢键贡献
根据本发明的一个优选的实施方式,所述聚合物具有在-70℃至160℃、优选地0℃至150℃、更优选地50℃至140℃、最优选地70℃至130℃范围内的玻璃化转变温度。可通过测量聚合物的DSC(DINENISO11357,加热速率是10℃/分钟)来确定所述玻璃化转变温度。
本发明的组合物包含至少一种溶剂,优选地至少一种芳族溶剂。所述溶剂优选地选自芳族烃,如甲苯,邻二甲苯、间二甲苯或对二甲苯,三甲基苯(例如1,2,3-三甲基苯、1,2,4-三甲基苯和1,3,5-三甲基苯),四氢化萘,其它的单烷基苯、二烷基苯、三烷基苯和四烷基苯(例如二乙基苯、甲基异丙基苯、四甲基苯等),芳族醚(例如苯甲醚、烷基苯甲醚,例如甲基苯甲醚的2、3和4异构体,二甲基苯甲醚的2,3-、2,4-、2,5-、2,6-、3,4-和3,5-异构体),萘衍生物,烷基萘衍生物(例如1-甲基萘和2-甲基萘),二氢萘和四氢萘衍生物。此外优选的是芳族酯(例如苯甲酸烷基酯)、芳族酮(例如苯乙酮、苯丙酮)、烷基酮(例如环己酮)、杂芳族溶剂(例如噻吩、单烷基噻吩、二烷基噻吩和三烷基噻吩、2-烷基噻唑、苯并噻唑等、吡啶)、卤族亚芳基和苯胺衍生物。这些溶剂可包含卤素原子。
特别优选的是:3-氟-三氟甲基苯、三氟甲基-苯、二烷、三氟甲氧基苯、4-氟-苯三氟化物、3-氟吡啶、甲苯、2-氟甲苯、2-氟-苯三氟化物、3-氟甲苯、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、1-氯-2,5-二氟苯、4-氯氟苯、氯苯、2-氯氟-苯、对二甲苯、间二甲苯、邻二甲苯、2,6-二甲基吡啶、2-氟-间二甲苯、3-氟-邻二甲苯、2-氯苯三氟化物、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、溴苯、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、苯并二氧杂环戊烯(benzenedioxol)、4-甲基苯甲醚、3-甲基苯甲醚、4-氟-3-甲基苯甲醚、1,2-二氯-苯、2-氟苯腈、4-氟邻二甲氧基苯、2,6-二甲基苯甲醚、苯胺、3-氟苯腈、2,5-二甲基苯甲醚、3,4-二甲基苯甲醚、2,4-二甲基苯甲醚、苯腈、3,5-二甲基苯甲醚、N,N-二甲基苯胺、1-氟-3,5-二甲氧基苯、苯乙酸酯(phenylacetate)、N-甲基苯胺、苯甲酸甲酯、N-甲基吡咯烷酮、吗啉、1,2-二氢萘、1,2,3,4-四氢萘、邻甲苯腈、邻二甲氧基苯、苯甲酸乙酯、N,N-二乙基苯胺、苯甲酸丙酯、1-甲基萘、苯甲酸丁酯、2-甲基联苯、2-苯基吡啶或2,2'-联甲苯。
更优选的是芳族烃,特别是甲苯、二甲基-苯(二甲苯)、三甲基苯、十二烷基苯、四氢化萘和甲基萘,芳族醚,特别是苯甲醚,和芳族酯,特别是苯甲酸烷基酯。
最优选的是芳族醚,特别是苯甲醚和其衍生物,例如烷基苯甲醚,和芳族酯,特别是苯甲酸甲酯。
这些溶剂可以以两种、三种或更多种的混合物使用。
优选的有机溶剂可以包含如下的汉森溶解度参数:在17.0至23.2MPa0.5范围内的Hd,在0.2至12.5MPa0.5范围内的Hp和在0.9至14.2MPa0.5范围内的Hh。更优选的有机溶剂包含如下的汉森溶解度参数:在18.5至21.0MPa0.5范围内的Hd,在2.0至6.0MPa0.5范围内的Hp和在2.0至6.0MPa0.5范围内的Hh。
表2:有用的溶剂的汉森溶解度参数
Hd是指分散性贡献
Hp是指极性贡献
Hh是指氢键贡献
优选地,所述溶剂在所用压力下,优选地在大气压力(1013hPa)下,具有<300℃、更优选地≤260℃、最优选地≤220℃的沸点或升华温度。还可以例如通过施加热和/或减压来加速蒸发。可以通过使用具有至少100℃、优选地至少130℃的沸点的溶剂来实现出人预料的改进。
通常,所述有机溶剂可以包含至少28mN/m、优选地至少30mN/m、更优选地至少32mN/m、最优选地至少35mN/m的表面张力。可以在25℃下使用FTA(FirstTenAngstrom)1000接触角测定器或KrussDSA100来测定表面张力。如由RogerP.Woodward,Ph.D.“SurfaceTensionMeasurementsUsingtheDropShapeMethod(使用滴形法的表面张力测定)”公布的,可由FirstTenAngstrom获得所述方法的细节。优选地,可以使用悬滴法来测定表面张力。
为了作出粗略估计,可以通过HansenSolubilityParameters:AUser’sHandbook(汉森溶解度参数:用户手册),第二版,C.M.Hansen(2007),TaylorandFrancisGroup,LLC(HSPiP手册)中详细说明的公式,使用汉森溶解度参数来计算表面张力。
表面张力=0.0146×(2.28×δHd 2+δHp 2+δHh 2)×MVol0.2,其中:
Hd是指分散性贡献
Hp是指极性贡献
Hh是指氢键贡献
MVol是指摩尔体积。
可以根据如由Hanson和Abbot等提供的Practice(HSPiP)程序(第2版)中的汉森溶解度参数来确定所述汉森溶解度参数。
优选地,所述溶剂包含至少0.01、优选地至少0.1、更优选地至少1、最优选地至少10的相对蒸发速率(乙酸丁酯=100)。可根据DIN53170:2009-08来确定相对蒸发速率。为了作出粗略估计,可以利用如上文和下文所提及的HSPiP程序使用汉森溶解度参数来计算相对蒸发速率。
优选地,当将0.5w/w至1%w/w的聚合物溶解在所述有机溶剂中时,所述聚合物使所述溶剂粘度增加至少0.4cps。
本发明的组合物优选包含至少70重量%、更优选地至少80重量%、最优选地至少90重量%的有机溶剂。
根据本发明的组合物可另外包含一种或多种另外的组分,例如表面活性化合物、润滑剂、润湿剂、分散剂、疏水剂、粘着剂、流动改进剂、消泡剂、脱气剂、可以是反应性或无反应性的稀释剂、助剂、着色剂、染料或颜料、敏化剂、稳定剂、纳米粒子或抑制剂。然而,这些另外的组分不应该具氧化性或者以其它方式能够与有机发光材料和/或电荷传输材料化学地反应,或者应该对有机发光材料和/或电荷传输材料具有电掺杂作用。
可以利用挥发性润湿剂来实现令人惊讶的改进。如上文和下文所用的术语“挥发性”指的是,所述试剂在有机发光材料和/或电荷传输材料已经沉积在OLED器件的基底上之后,在不显著破坏这些材料或所述OLED器件的条件(如温度和/或减压)下,可以通过蒸发从这些材料中除去。优选地,这意味着润湿剂在所用压力下,优选地在大气压力(1013hPa)下,具有≤350℃、更优选地≤300℃、最优选地≤250℃的沸点或升华温度。还可以例如通过施加热和/或减压来加速蒸发。
可以通过包含具有类似沸点的挥发性组分的组合物来实现令人惊讶的效果。优选地,润湿剂与有机溶剂的沸点差异在-50℃至50℃范围内,更优选地在-30℃至30℃范围内,最优选地在-20℃至20℃范围内。
优选的润湿剂是非芳族化合物。进一步优选的润湿剂是非离子型化合物。特别有用的润湿剂包含至多35mN/m、优选地至多30mN/m、更优选地至多25mN/m的表面张力。可以在25℃下使用FTA(FirstTenAngstrom)1000接触角测定器或KrussDSA100来测量表面张力。如由RogerP.Woodward,Ph.D.“SurfaceTensionMeasurementsUsingtheDropShapeMethod(使用滴形法的表面张力测定)”公布的,可由FirstTenAngstrom获得所述方法的细节。优选地,可以使用悬滴法来测定表面张力。
根据本发明的一个特别方面,有机溶剂与润湿剂的表面张力差异优选地是至少1mN/m,更优选地是至少5mN/m,最优选地是至少10mN/m。
根据本发明的一个特别方面,所述润湿添加剂包含至少0.01、优选地至少0.1、更优选地至少1、最优选地至少10的相对蒸发速率(乙酸丁酯=100)。
利用包含具有类似相对蒸发速率(乙酸丁酯=100)的溶剂和润湿剂的组合物可以实现出人预料的改进。优选地,润湿剂与有机溶剂的相对蒸发速率(乙酸丁酯=100)的差异在-20至20范围内,更优选地在-10至10范围内。根据本发明的一个优选的实施方式,润湿剂的相对蒸发速率(乙酸丁酯=100)对有机溶剂的相对蒸发速率(乙酸丁酯=100)的比可在230:1至1:230、优选地20:1至1:20、更优选地5:1至1:5的范围内。
利用包含至少100g/摩尔、优选地至少150g/摩尔、更优选地至少180g/摩尔、最优选地至少200g/摩尔的分子量的润湿剂可以实现出人预料的改进。不氧化有机半导电材料或者以其它方式与有机半导电材料化学反应的合适且优选的润湿剂选自硅氧烷、烷烃、胺、烯烃、炔烃、醇和/或这些化合物的卤化衍生物。此外,可以使用氟醚、氟酯和/或氟酮。更优选地,这些化合物选自具有6至20个碳原子、特别是8至16个碳原子的甲基硅氧烷;C7-C14烷烃、C7-C14烯烃、C7-C14炔烃、具有7至14个碳原子的醇、具有7至14个碳原子的氟醚、具有7至14个碳原子的氟酯和具有7至14个碳原子的氟酮。最优选的润湿剂是具有8至14个碳原子的甲基硅氧烷。
具有7至14个碳原子的有用且优选的烷烃包括庚烷、辛烷、壬烷、癸烷、十一碳烷、十二碳烷、十三碳烷、十四碳烷、3-甲基庚烷、4-乙基庚烷、5-丙基癸烷、三甲基环己烷和十氢化萘。
具有7至14个碳原子的卤代烷烃包括1-氯庚烷、1,2-二氯辛烷、四氟辛烷、十氟十二碳烷、全氟-壬烷、1,1,1-三氟甲基癸烷和全氟甲基十氢化萘。
具有7至14个碳原子的有用且优选的烯烃包括庚烯、辛烯、壬烯、1-癸烯、4-癸烯、十一碳烯、十二碳烯、十三碳烯、十四碳烯、3-甲基庚烯、4-乙基庚烯、5-丙基癸烯和三甲基环己烯。
具有7至14个碳原子的卤代烯烃包括1-氯庚烯、1,2-二氯辛烯、四氟辛烯、十氟十二碳烯、全氟-壬烯和1,1,1-三氟甲基癸烯。
具有7至14个碳原子的有用且优选的炔烃包括庚炔、辛炔、壬炔、1-癸炔、4-癸炔、十一碳炔、十二碳炔、十三碳炔、十四碳炔、3-甲基庚炔、4-乙基庚炔、5-丙基癸炔和三甲基环己炔。
具有7至14个碳原子的卤代炔烃包括1-氯庚炔、1,2-二氯辛炔、四氟辛炔、十氟十二碳炔、全氟-壬炔和1,1,1-三氟甲基癸炔。
具有7至14个碳原子的有用且优选的醇包括3,5-二甲基-1-己炔-3-醇、庚醇、辛醇、壬醇、癸醇、十一烷醇、十二烷醇、十三烷醇、十四烷醇、3-甲基庚醇、4-乙基庚醇、5-丙基癸醇、三甲基环己醇和羟基十氢化萘。
具有7至14个碳原子的卤代烷醇包括1-氯-庚醇、1,2-二氯辛醇、四氟辛醇、十氟十二烷醇、全氟壬醇、1,1,1-三氟甲基癸醇和2-三氟甲基-1-羟基十氢化萘。
具有4至15个碳原子的有用且优选的胺包括己基胺、三丙基胺、三丁基胺、二丁基胺、哌嗪、庚基胺、辛基胺、壬基胺、癸基胺、十一烷基胺、十二烷基胺、十三烷基胺、十四烷基胺、3-甲基庚基胺、4-乙基庚基胺、5-丙基癸基胺、三甲基环己基胺。
具有4至15个碳原子的卤代胺包括1-氯庚基-胺、1,2-二氯辛基胺、四氟辛基胺、十氟十二烷基-胺、全氟壬基胺、1,1,1-三氟甲基癸基胺、全氟三丁基胺和全氟三戊基胺。
具有7至14个碳原子的有用且优选的氟醚包括3-乙氧基-1,1,1,2,3,4,4,5,5,6,6,6-十二氟-2-三氟甲基-己烷、3-丙氧基-1,1,1,2,3,4,4,5,5,6,6,6-十二氟-2-三氟甲基-己烷、3-乙氧基-1,1,1,2,3,4,4,5,5,6,6,7,7,7-十四氟-2-三氟甲基-庚烷、3-乙氧基-1,1,1,2,3,4,4,5,5,5-十氟-2-三氟甲基-戊烷和3-丙氧基-1,1,1,2,3,4,4,5,5,5-十氟-2-三氟甲基-戊烷。
具有7至14个碳原子的有用且优选的氟酯包括乙酸3-(1,1,1,2,3,4,4,5,5,6,6,6-十二氟-2-三氟甲基-己基)酯、丙酸3-(1,1,1,2,3,4,4,5,5,6,6,6-十二氟-2-三氟甲基-己基)酯、乙酸3-(1,1,1,2,3,4,4,5,5,6,6,7,7,7-十四氟-2-三氟甲基-庚基)酯、乙酸3-(1,1,1,2,3,4,4,5,5,5-十氟-2-三氟甲基-戊基)酯和丙酸3-(1,1,1,2,3,4,4,5,5,5-十氟-2-三氟甲基-戊基)酯。
具有7至14个碳原子的有用且优选的氟酮包括3-(1,1,1,2,3,4,4,5,5,6,6,6-十二氟-2-三氟甲基-己基)乙基酮、3-(1,1,1,2,3,4,4,5,5,6,6,6-十二氟-2-三氟甲基-己基)丙基-酮、3-(1,1,1,2,3,4,4,5,5,6,6,7,7,7-十四氟-2-三氟甲基-庚基)乙基酮、3-(1,1,1,2,3,4,4,5,5,5-十氟-2-三氟甲基-戊基)乙基酮和3-(1,1,1,2,3,4,4,5,5,5-十氟-2-三氟甲基-戊基)丙基酮。
有用且优选的硅氧烷包括六甲基二硅氧烷、八甲基-三硅氧烷、十甲基四硅氧烷、十二甲基五硅氧烷和十四甲基六硅氧烷。
可用作润湿剂的化合物的实例在表3中公开。利用如上文和下文所提及的Hanson和Abbott等提供的HSPiP程序使用汉森溶解度参数来计算所提供的相对蒸发速率(RER)和表面张力值。
表3:优选的润湿剂
Hd是指分散性贡献
Hp是指极性贡献
Hh是指氢键贡献
MVol是指摩尔体积。
优选地,所述组合物包含至多5重量%、更优选地至多3重量%、最优选地至多1重量%的润湿添加剂。优选地,所述组合物包含0.01重量%至5重量%、更优选地0.1重量%至3重量%的润湿剂。
优选地,所述溶剂应该被选择以使得它可以与润湿剂一起,优选地在同一加工步骤中,从包含发光材料和/或电荷传输材料的涂布或印刷层中蒸发。用于除去溶剂和挥发性添加剂的加工温度应该被选择以使得不损坏包含有机发光材料和/或电荷传输材料的层。优选地,沉积加工温度是从室温(RT;约25℃)至135℃,更优选地是从RT至100℃。
优选地,本发明的组合物包含在20mN/m至60mN/m、更优选地25mN/m至45mN/m范围内的表面张力。可使用如上文和下文所提及的FTA(FirstTenAngstrom)1000接触角测定器或KrussDSA100来测量所述表面张力。通过以适当方式选择聚合物粘结剂和溶剂可以实现所述表面张力。如上文所提及的汉森溶解度参数的使用为本领域技术人员提供了有用的帮助。此外,通过使用润湿剂、优选地如上文所提及的挥发性润湿剂可以实现所述表面张力。
优选地,所述组合物具有在1mPas至100mPas范围内、优选地在2.0mPas至40mPas范围内、更优选地在2.1mPas至20mPas范围内、最优选地在2.1mPas至15mPas范围内的粘度。在25℃的温度下通过在由Haake制造的MARSIII流变仪上进行测定来确定所述粘度。这是使用1°锥板几何结构测定的。
优选地,所述组合物可以被过滤至例如1微米或更小。
在制备OLED器件的过程期间,将包含有机发光材料和/或电荷传输材料的层沉积在基底上,接着除去溶剂以及任何存在的一种或多种挥发性导电添加剂,以形成膜或层。
所述基底可以是适于制备OLED器件的任何基底,或者也可以是所述OLED器件或其一部分。合适且优选的基底例如是玻璃,ITO涂布玻璃,包括PEDOT、PANI等的具有预涂布层的ITO玻璃,聚对苯二甲酸乙二醇酯(PET)、聚萘二甲酸乙二醇酯(PEN)、聚酰亚胺的柔性膜,和具有ITO的柔性膜,或其它导电层和阻挡层例如Vitex膜。
可以通过本领域技术人员已知和在文献中描述的标准方法来实现包含有机发光材料和/或电荷传输材料的层的沉积。合适且优选的沉积方法包括液体涂布和印刷技术。非常优选的沉积方法包括(但不限于)浸涂、旋涂、喷墨印刷、喷嘴印刷、凸版印刷(letter-pressprinting)、丝网印刷、凹版印刷、刮刀涂布、辊筒印刷、反向辊筒印刷、平版光刻印刷(offsetlithographyprinting)、柔性版印刷、轮转机印刷、喷涂、帘涂、刷涂、气刷涂布、狭缝式染料涂布或移印。凹版、柔性版和喷墨印刷是优选的。
优选通过蒸发,例如通过使沉积层暴露于高温和/或减压,优选地在50至200℃下,更优选地在60至135℃下来实现溶剂和任何一种或多种挥发性导电添加剂的除去。
包含有机发光材料和/或电荷传输材料的层的厚度优选是1nm至500nm,更优选是2至150nm。
除了如上文和下文所述的材料和方法之外,可以从本领域技术人员已知和在文献中描述的标准材料和标准方法来制备OLED器件和其组件。
应理解,可以在仍落在本发明范围内的同时对本发明的前述实施方式做出变化。除非另外说明,否则本说明书中公开的每种特征可被提供相同、等效或类似目的的可选特征代替。因此,除非另外说明,否则所公开的每种特征仅是通用系列的等效或类似特征的一个实例。
本说明书中公开的所有特征能够以除其中这样的特征和/或步骤中的至少一些相互排斥的组合外的任何组合进行组合。特别是,本发明的优选特征可应用于本发明的所有方面并且可以任何组合使用。同样,以非必要的组合描述的特征可单独地(而非组合)使用。
将理解,上述的许多特征,特别是优选实施方式的许多特征,自身是发明性的,而不仅仅是作为本发明的实施方式的一部分。除了当前要求保护的任何发明或作为当前要求保护的任何发明的可选方案,可对这些特征寻求独立的保护。
除非上下文另外明确说明,否则如本文所用的,本文中术语的复数形式被理解为包括单数形式,反之亦然。
在整个本说明书的描述和权利要求书中,词语“包含”和“含有”和所述词语的变体是指“包括但不限于”,而不旨在(并且不)排除其它组分。
术语“聚合物”包括均聚物和共聚物,例如统计、交替或嵌段共聚物。另外,如下文中使用的术语“聚合物”还包括低聚物和树枝状大分子。树枝状大分子通常是由多官能核心基团组成的支链大分子化合物,以规律方式在所述多官能核心基团上添加其它支链单体,得到树状结构,如在例如M.Fischer和F.Angew.Chem.,Int.Ed.(德国应用化学)1999,38,885中所述的。
术语“共轭聚合物”是指在其骨架(或主链)中主要含有具有sp2杂化或任选地sp杂化的C原子的聚合物,所述C原子也可被杂原子代替,使得一个π轨道与另一个跨过间隔的σ键相互作用。在最简单的情况下,这例如是具有交替的碳-碳(或碳-杂原子)单键和多键(例如双键或三键)的骨架,但确实也包括具有如1,3-亚苯基的单元的聚合物。“主要地”在这方面是指具有可导致共轭中断的天然地(自发地)存在的缺陷的聚合物仍然被视为共轭聚合物。在这个含义中还包括如下的聚合物,其中骨架包含例如如芳基胺、芳基膦和/或某些杂环(即通过N、O、P或S原子的共轭)和/或金属有机络合物(即通过金属原子的共轭)的单元。术语“共轭的连接基团”是指连接两个由具有sp2杂化或sp杂化的C原子或杂原子组成的环(通常是芳族环)的基团。也参见“IUPACCompendiumofChemicalterminology(IUPAC化学术语目录),电子版”。
除非另外说明,否则分子量以除非另外说明否则通过凝胶渗透色谱法(GPC)相对于聚苯乙烯标准物测定的数均分子量Mn或重均分子量Mw给出。
聚合度(n)是指数均聚合度,除非另外说明,否则以n=Mn/MU给出,其中MU是单个重复单元的分子量。
术语“小分子”是指单体的、即非聚合的化合物。
除非另外说明,否则固体的百分比是重量百分比(“重量%”),液体(如例如在溶剂混合物中)的百分比或比率是体积百分比(“体积%”),并且所有温度以摄氏度(℃)给出。
除非另外说明,否则以百分比或ppm给出的混合物组分如导电添加剂的浓度或比例与包括溶剂的整个制剂有关。
现在将通过参考以下实施例来更详细地描述本发明,所述实施例仅是示例性的,而不限制本发明的范围。
实施例
比较例1
通过将根据式(A)的磷光化合物
根据式(B)的主体材料
和根据式(C)的主体材料
以1:2:2的重量比率A:B:C混合并将所得混合物溶解在苯甲醚中来制备印刷油墨。半导体化合物的浓度是约2.5重量%。
使用RKK印刷打样机将OLED油墨凹版印刷在覆盖有10个基底(25×25mm)的PET基底(120×220mm)上,所述基底各自具有4个ITO像素结构和凹版印刷的PEDOT层。使用两个干燥程序,在120℃下的热板以及在120℃下的热空气对流干燥器,以评估膜品质差异。
这种制剂的凹版印刷得到极其差的膜品质,如图3中可见的。
比较例2
基本上重复比较例1。然而,已经向印刷油墨添加惰性聚苯乙烯粘结剂。所述印刷油墨包含0.5重量%的具有2,000,000g/摩尔的Mw的聚苯乙烯(如由SigmaAldrich提供)和2.5重量%的如比较例1中所提及的半导体化合物。
在PEDOT和PET上的润湿好于比较例1中,但不良。润湿显示显著的问题,如图4中可见的。
比较例3
基本上重复比较例1。然而,已经向印刷油墨添加惰性聚苯乙烯粘结剂。所述印刷油墨包含1.0重量%的具有2,000,000g/摩尔的Mw的聚苯乙烯(如由SigmaAldrich提供)和2.5重量%的如比较例1中所提及的半导体化合物。
相比于比较例2,在PEDOT上达到更好的润湿。然而,在层中可见大的针孔,如图5中可见的。然而,相比于比较例1和2,结果得以改进。
实施例4
基本上重复比较例1。然而,已经向印刷油墨添加惰性聚(甲基丙烯酸甲酯)粘结剂。所述印刷油墨包含0.25重量%的具有2,400,000g/摩尔的Mw的聚(甲基丙烯酸甲酯)(如由SigmaAldrich提供)和2.5重量%的如比较例3中所提及的半导体化合物。
在PEDOT层上达到更好的润湿。相比于比较例3,结果得以改进。
实施例5
基本上重复比较例1。然而,已经向印刷油墨添加惰性聚(甲基丙烯酸甲酯)粘结剂。所述印刷油墨包含0.5重量%的具有2,400,000g/摩尔的Mw的聚(甲基丙烯酸甲酯)(如由SigmaAldrich提供)和2.5重量%的如实施例4中所提及的半导体化合物。
在干燥后,已经达到非常良好的膜品质和在PEDOT上的润湿。相比于实施例4,结果得以改进,如图6中可见的。
器件实施例6和7
溶液加工的OLED的器件制备
文献中描述了关于从溶液中制备有机发光二极管的许多实例,主要是用于聚合物器件(“PLED”,例如WO2004/037887A2)。为了说明本发明制剂不仅产生更好的膜,而且性能良好,在标准测试设置中制造OLED器件。典型的设置描绘于图1中,所用的器件布局示于图2中。ITO(氧化铟锡)是如下的透明空穴注入阳极,其通过溅射沉积在PET箔上并通过凹版印刷光刻进行结构化以获得十个尺寸为6×4mm的各自由4个像素组成的基底。在本情况下,所述基底是自制备的。
在洁净室环境中在超声浴中使用丙酮和IPA对175μm厚的聚对苯二甲酸乙二醇酯(PET)基底进行清洁。然后用UV/臭氧处理将表面活化。通过凹版印刷在基底上沉积约60nm的PEDOT作为第一层并在130℃下干燥60秒。(PEDOT是PEDOT、聚噻吩和PSSH、聚磺酸的水基分散液,获自H.C.Starck,Goslar;此处使用的是CleviosP4083AI,但来自H.C.Starck的其它PEDOT产品或来自其它供应商的“缓冲”材料也将起作用)。EML的膜厚度是约100nm,并且将基底在130℃下再退火10分钟以除去剩余溶剂。溶液粘度随着固体浓度,即随着小分子、聚合物含量和惰性成膜剂含量而改变。在以下实施例中,使用苯甲醚作为溶剂,但也可以使用其它溶剂(参见说明书)。在这种情况下,必须相应地调整凹版印刷条件和干燥程序。使用在UV光激发下的CanonEOS550D数码相机和具有LMPLFLN20倍物镜的OlympusBX51偏光显微镜在印刷操作后检查干燥层。
为了进行电接触,将阴极结构通过金属掩模真空沉积在有机膜的顶部。所述阴极可由仅一种金属(例如Yb)组成,是反应性的两层结构且因此是电子注入金属(例如Mg、Ba、Sr等)与封盖金属(通常是Al或Ag)组合,是含有碱金属或碱土金属氟化物或氧化物作为第一沉积层(例如LiF、Li2O、BaF2、BaO、MgO、NaF等)的双层或三层结构,或者具有一个或多个真空沉积的电子传输层,接着是适当的电子注入金属或金属氟化物、氧化物或喹啉盐。在本情况下,仅沉积Ca和Al以保持器件简单,并且显示即使这样的简单设置也能够提供非常好的器件。为了封闭有机和阴极结构免于水分和/或氧气,将所述器件封装并且然后可以在手套箱外部处理。
用来自Botest的设置进行表征。将所述器件固定在样品固持器中,所述样品固持器具有将阳极和阴极连接至测定电路的弹簧接触。将具有眼睛校正滤镜的光电二极管紧密放置在顶部以防止外部光线篡改结果。然后电压以0.2V的步长逐步增大到10V,同时测定通过样品的电流和来自光电二极管的光电流。以这种方式收集所谓的IVL数据(电流、电压、亮度)。重要的数据是最大效率(以cd/A计量)、外量子效率(EQE)(以%计量)和特定亮度所需的电压。
实施例6和7:
具有惰性聚苯乙烯(PS)粘结剂的器件与具有惰性聚(甲基丙烯酸甲酯)(PMMA)粘
结剂的器件的比较
比较例6
将化合物(A)、(B)和(C)以25g/l的浓度溶解在苯甲醚中,另外以5g/l的浓度添加聚苯乙烯(2.000.000g/摩尔,Aldrich)作为惰性粘结剂以改进成膜性并且进行凹版印刷。器件表征结果示于表4中。
实施例7
将化合物(A)、(B)和(C)以25g/l的浓度溶解在苯甲醚中,另外以5g/l的浓度添加聚(甲基丙烯酸甲酯)(2.400.000g/摩尔,Aldrich)作为惰性粘结剂以改进成膜性并且进行凹版印刷。器件表征结果示于表4中。
表4
实施例 | 最大效率[cd/A] | 添加剂 |
6 | 6 | 聚苯乙烯 |
7 | 20 | 聚(甲基丙烯酸甲酯) |
Claims (16)
1.一种组合物,所述组合物包含一种或多种具有至多5000g/摩尔的分子量的有机发光材料和/或电荷传输材料、一种或多种有机溶剂和一种或多种聚合物,其特征在于所述聚合物包含丙烯酸酯和/或甲基丙烯酸酯单元。
2.根据权利要求1所述的组合物,其特征在于所述聚合物包含5摩尔%至100摩尔%的选自丙烯酸酯和/或甲基丙烯酸酯单元的重复单元。
3.根据权利要求1或2所述的组合物,其特征在于所述丙烯酸酯和/或甲基丙烯酸酯单元选自具有C1-10烷基基团、C3-8环烷基基团、C6-14芳基基团或C2-13杂芳基基团作为酯基团的丙烯酸酯和/或甲基丙烯酸酯单元。
4.根据权利要求1至3中的一项或多项所述的组合物,其特征在于所述聚合物具有至少500.000g/摩尔的重均分子量Mw。
5.根据权利要求1至4中的一项或多项所述的组合物,其特征在于所述组合物包含在25℃下在1至100mPas范围内的粘度。
6.根据权利要求1至5中的一项或多项所述的组合物,其特征在于所述聚合物具有在-70℃至160℃范围内的玻璃化转变温度。
7.根据权利要求1至6中的一项或多项所述的组合物,其特征在于所述组合物包含在0.01重量%至20重量%范围内的所述聚合物。
8.根据权利要求1至7中的一项或多项所述的组合物,其特征在于所述有机溶剂是芳族有机溶剂。
9.根据权利要求8所述的组合物,其特征在于所述有机溶剂选自芳族烃、芳族醚、芳族酯、芳族酮、杂芳族溶剂和苯胺衍生物。
10.根据权利要求1至9中的一项或多项所述的组合物,其特征在于所述有机溶剂具有≤260℃的沸点。
11.根据权利要求1至10中的一项或多项所述的组合物,其特征在于所述组合物包含至少80重量%的所述有机溶剂。
12.根据权利要求1至11中的一项或多项所述的组合物,其特征在于所述一种或多种具有至多5000g/摩尔的分子量的有机发光材料是有机磷光化合物,所述有机磷光化合物发光并且另外含有至少一个具有大于38的原子序数的原子。
13.根据权利要求12所述的组合物,其特征在于所述有机磷光化合物选自式(1)至(4)的化合物:
其中
DCy在每次出现时相同或不同地是含有至少一个供体原子、优选地氮、呈碳烯形式的碳或磷的环状基团,所述环状基团通过所述供体原子键合至金属,并且所述环状基团又可带有一个或多个取代基R1;所述基团DCy和CCy通过共价键彼此连接;
CCy在每次出现时相同或不同地是含有碳原子的环状基团,所述环状基团通过所述碳原子键合至金属并且所述环状基团又可以带有一个或多个取代基R1;
A在每次出现时相同或不同地是单阴离子二齿螯合配体,优选地是二酮配体;
R1在每种情况下相同或不同并且是F,Cl,Br,I,NO2,CN,具有1至20个碳原子的直链、支链或环状的烷基或烷氧基基团,其中一个或多个非相邻的CH2基团可被-O-、-S-、-NR2-、-CONR2-、-CO-O-、-C=O-、-CH=CH-或-C≡C-代替,并且其中一个或多个氢原子可被F代替,或者具有4至14个碳原子并且可被一个或多个非芳族R1基团取代的芳基或杂芳基基团,并且在同一环上或在两个不同环上的多个取代基R1又可一起形成单环或多环的脂族或芳族环系;并且
R2在每种情况下相同或不同并且是具有1至20个碳原子的直链、支链或环状的烷基或烷氧基基团,其中一个或多个非相邻的CH2基团可被-O-、-S-、-CO-O-、-C=O-、-CH=CH-或-C≡C-代替,并且其中一个或多个氢原子可被F代替,或者具有4至14个碳原子并且可被一个或多个非芳族R1基团取代的芳基或杂芳基基团。
14.根据权利要求1至13中的一项或多项所述的组合物,其特征在于所述组合物包含0.25重量%至5重量%的具有至多5000g/摩尔的分子量的有机发光材料和/或电荷传输材料。
15.根据权利要求1至14中的一项或多项所述的组合物作为用于制备有机电致发光(EL)器件、优选地OLED器件的涂料或印刷油墨的用途。
16.一种有机电致发光器件、优选地OLED器件,所述器件是从根据权利要求1至14中的一项或多项所述的组合物制备的。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101663337A (zh) * | 2007-04-17 | 2010-03-03 | 通用电气公司 | 聚咔唑基(甲基)丙烯酸酯光发射组合物 |
CN102668152A (zh) * | 2009-12-23 | 2012-09-12 | 默克专利有限公司 | 包括聚合粘结剂的组合物 |
TW201245439A (en) * | 2011-03-29 | 2012-11-16 | Toppan Printing Co Ltd | Ink composition, organic electroluminescence element using same and method for manufacturing same |
Family Cites Families (87)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4780536A (en) | 1986-09-05 | 1988-10-25 | The Ohio State University Research Foundation | Hexaazatriphenylene hexanitrile and its derivatives and their preparations |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
JPH061973A (ja) | 1992-06-18 | 1994-01-11 | Konica Corp | 有機エレクトロルミネッセンス素子 |
US5837166A (en) | 1993-09-29 | 1998-11-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and arylenediamine derivative |
EP0650955B1 (en) | 1993-11-01 | 1998-08-19 | Hodogaya Chemical Co., Ltd. | Amine compound and electro-luminescence device comprising same |
DE59510315D1 (de) | 1994-04-07 | 2002-09-19 | Covion Organic Semiconductors | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
DE69511755T2 (de) | 1994-04-26 | 2000-01-13 | Tdk Corp | Phenylanthracenderivat und organisches EL-Element |
US6344283B1 (en) | 1996-12-28 | 2002-02-05 | Tdk Corporation | Organic electroluminescent elements |
US5952778A (en) | 1997-03-18 | 1999-09-14 | International Business Machines Corporation | Encapsulated organic light emitting device |
DE19812259A1 (de) | 1998-03-20 | 1999-10-21 | Bayer Ag | EL-Anordnung auf Basis von tert.-Aminen, in Alkohol löslichen Alq3-Derivaten bzw. Mischungen und polymeren Bindern |
US5935721A (en) | 1998-03-20 | 1999-08-10 | Eastman Kodak Company | Organic electroluminescent elements for stable electroluminescent |
DE19825737A1 (de) * | 1998-06-09 | 1999-12-16 | Bayer Ag | Elektrolumineszierende Anordnungen mit N-Alkyl-2,2'-imino-bis-(8-hydroxychinolin)-Metallkomplexen |
JP3302945B2 (ja) | 1998-06-23 | 2002-07-15 | ネースディスプレイ・カンパニー・リミテッド | 新規な有機金属発光物質およびそれを含む有機電気発光素子 |
JP4429438B2 (ja) | 1999-01-19 | 2010-03-10 | 出光興産株式会社 | アミノ化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
CN101312235B (zh) | 1999-05-13 | 2010-06-09 | 普林斯顿大学理事会 | 基于电致磷光的极高效有机发光器件 |
WO2001041512A1 (en) | 1999-12-01 | 2001-06-07 | The Trustees Of Princeton University | Complexes of form l2mx as phosphorescent dopants for organic leds |
KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
JP4220644B2 (ja) | 2000-02-14 | 2009-02-04 | 三井化学株式会社 | アミン化合物および該化合物を含有する有機電界発光素子 |
US6660410B2 (en) | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
EP2566302B1 (en) | 2000-08-11 | 2015-12-16 | The Trustees of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorence |
JP4154138B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
JP4154140B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
JP4154139B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子 |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
DE10207859A1 (de) | 2002-02-20 | 2003-09-04 | Univ Dresden Tech | Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung |
ITRM20020411A1 (it) | 2002-08-01 | 2004-02-02 | Univ Roma La Sapienza | Derivati dello spirobifluorene, loro preparazione e loro uso. |
ATE452954T1 (de) | 2002-08-23 | 2010-01-15 | Idemitsu Kosan Co | Organische elektrolumineszenzvorrichtung und anthracenderivat |
US20060035109A1 (en) | 2002-09-20 | 2006-02-16 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
US6818919B2 (en) | 2002-09-23 | 2004-11-16 | Air Products And Chemicals, Inc. | Light emitting layers for LED devices based on high Tg polymer matrix compositions |
DE10249723A1 (de) | 2002-10-25 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Arylamin-Einheiten enthaltende konjugierte Polymere, deren Darstellung und Verwendung |
JP4287198B2 (ja) | 2002-11-18 | 2009-07-01 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
US20060063027A1 (en) | 2002-12-23 | 2006-03-23 | Covion Organic Semiconductors Gmbh | Organic electroluminescent element |
DE10310887A1 (de) | 2003-03-11 | 2004-09-30 | Covion Organic Semiconductors Gmbh | Matallkomplexe |
WO2004080975A1 (ja) | 2003-03-13 | 2004-09-23 | Idemitsu Kosan Co., Ltd. | 新規含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
JP4411851B2 (ja) | 2003-03-19 | 2010-02-10 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
KR101035795B1 (ko) | 2003-04-10 | 2011-05-20 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그것을 이용한 유기 전기발광 소자 |
WO2004093207A2 (de) | 2003-04-15 | 2004-10-28 | Covion Organic Semiconductors Gmbh | Mischungen von organischen zur emission befähigten halbleitern und matrixmaterialien, deren verwendung und elektronikbauteile enthaltend diese mischungen |
US7326475B2 (en) | 2003-04-23 | 2008-02-05 | Konica Minolta Holdings, Inc. | Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display |
GB0311234D0 (en) * | 2003-05-16 | 2003-06-18 | Isis Innovation | Organic phosphorescent material and organic optoelectronic device |
WO2004101682A1 (ja) | 2003-05-16 | 2004-11-25 | Sumitomo Chemical Company, Limited | 組成物および高分子発光素子 |
TWI224473B (en) | 2003-06-03 | 2004-11-21 | Chin-Hsin Chen | Doped co-host emitter system in organic electroluminescent devices |
DE10345572A1 (de) | 2003-09-29 | 2005-05-19 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
US7795801B2 (en) | 2003-09-30 | 2010-09-14 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, display and compound |
DE10350722A1 (de) | 2003-10-30 | 2005-05-25 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
ATE475971T1 (de) | 2003-11-28 | 2010-08-15 | Merck Patent Gmbh | Organische halbleiterschicht-formulierungen mit polyacenen und organischen binderpolymeren |
DE10357044A1 (de) | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten |
US7252893B2 (en) | 2004-02-17 | 2007-08-07 | Eastman Kodak Company | Anthracene derivative host having ranges of dopants |
DE102004008304A1 (de) | 2004-02-20 | 2005-09-08 | Covion Organic Semiconductors Gmbh | Organische elektronische Vorrichtungen |
US7326371B2 (en) | 2004-03-25 | 2008-02-05 | Eastman Kodak Company | Electroluminescent device with anthracene derivative host |
US7790890B2 (en) | 2004-03-31 | 2010-09-07 | Konica Minolta Holdings, Inc. | Organic electroluminescence element material, organic electroluminescence element, display device and illumination device |
KR100787425B1 (ko) | 2004-11-29 | 2007-12-26 | 삼성에스디아이 주식회사 | 페닐카바졸계 화합물 및 이를 이용한 유기 전계 발광 소자 |
DE102004023277A1 (de) | 2004-05-11 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Neue Materialmischungen für die Elektrolumineszenz |
ATE473230T1 (de) | 2004-05-19 | 2010-07-15 | Merck Patent Gmbh | Metallkomplexe |
TWI327563B (en) | 2004-05-24 | 2010-07-21 | Au Optronics Corp | Anthracene compound and organic electroluminescent device including the anthracene compound |
JP4862248B2 (ja) | 2004-06-04 | 2012-01-25 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
TW200613515A (en) | 2004-06-26 | 2006-05-01 | Merck Patent Gmbh | Compounds for organic electronic devices |
DE102004031000A1 (de) | 2004-06-26 | 2006-01-12 | Covion Organic Semiconductors Gmbh | Organische Elektrolumineszenzvorrichtungen |
ITRM20040352A1 (it) | 2004-07-15 | 2004-10-15 | Univ Roma La Sapienza | Derivati oligomerici dello spirobifluorene, loro preparazione e loro uso. |
DE102004034517A1 (de) | 2004-07-16 | 2006-02-16 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
EP1655359A1 (de) | 2004-11-06 | 2006-05-10 | Covion Organic Semiconductors GmbH | Organische Elektrolumineszenzvorrichtung |
TW200639140A (en) | 2004-12-01 | 2006-11-16 | Merck Patent Gmbh | Compounds for organic electronic devices |
TW200634020A (en) | 2004-12-09 | 2006-10-01 | Merck Patent Gmbh | Metal complexes |
KR20070091319A (ko) | 2005-01-05 | 2007-09-10 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 이를 이용한 유기 전기발광 소자 |
CN101115762A (zh) | 2005-02-03 | 2008-01-30 | 默克专利有限公司 | 金属络合物 |
JP2006253445A (ja) | 2005-03-11 | 2006-09-21 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子 |
JP4263700B2 (ja) | 2005-03-15 | 2009-05-13 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2006100896A1 (ja) | 2005-03-18 | 2006-09-28 | Idemitsu Kosan Co., Ltd. | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
KR101289923B1 (ko) | 2005-05-03 | 2013-07-25 | 메르크 파텐트 게엠베하 | 유기 전계발광 장치 및 그에 사용되는 붕산 및 보린산유도체 |
DE102005023437A1 (de) | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
EP1956022B1 (en) | 2005-12-01 | 2012-07-25 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent element and organic electroluminescent element |
DE102005058557A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102005058543A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
US8440324B2 (en) * | 2005-12-27 | 2013-05-14 | E I Du Pont De Nemours And Company | Compositions comprising novel copolymers and electronic devices made with such compositions |
DE102006015183A1 (de) | 2006-04-01 | 2007-10-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006025777A1 (de) | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006025846A1 (de) | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006031990A1 (de) | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
EP1883124A1 (en) | 2006-07-27 | 2008-01-30 | IEE INTERNATIONAL ELECTRONICS & ENGINEERING S.A. | Organic light emitting material formulation |
WO2008056746A1 (fr) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
DE102007002714A1 (de) | 2007-01-18 | 2008-07-31 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102007024850A1 (de) | 2007-05-29 | 2008-12-04 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102008027005A1 (de) | 2008-06-05 | 2009-12-10 | Merck Patent Gmbh | Organische elektronische Vorrichtung enthaltend Metallkomplexe |
DE102008033943A1 (de) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008035413A1 (de) | 2008-07-29 | 2010-02-04 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
DE102008036982A1 (de) | 2008-08-08 | 2010-02-11 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
-
2014
- 2014-11-11 US US15/101,066 patent/US20160301003A1/en not_active Abandoned
- 2014-11-11 JP JP2016536834A patent/JP6716457B2/ja active Active
- 2014-11-11 EP EP14799670.6A patent/EP3077475B1/en active Active
- 2014-11-11 CN CN201480065940.7A patent/CN105793387B/zh active Active
- 2014-11-11 KR KR1020167017870A patent/KR20160094430A/ko not_active IP Right Cessation
- 2014-11-11 WO PCT/EP2014/003015 patent/WO2015082037A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101663337A (zh) * | 2007-04-17 | 2010-03-03 | 通用电气公司 | 聚咔唑基(甲基)丙烯酸酯光发射组合物 |
CN102668152A (zh) * | 2009-12-23 | 2012-09-12 | 默克专利有限公司 | 包括聚合粘结剂的组合物 |
TW201245439A (en) * | 2011-03-29 | 2012-11-16 | Toppan Printing Co Ltd | Ink composition, organic electroluminescence element using same and method for manufacturing same |
Also Published As
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WO2015082037A1 (en) | 2015-06-11 |
US20160301003A1 (en) | 2016-10-13 |
JP2017501263A (ja) | 2017-01-12 |
CN105793387B (zh) | 2019-04-30 |
EP3077475A1 (en) | 2016-10-12 |
KR20160094430A (ko) | 2016-08-09 |
JP6716457B2 (ja) | 2020-07-01 |
EP3077475B1 (en) | 2018-07-04 |
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