CN1871720B - 有机电致发光元件及其生产方法 - Google Patents
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Abstract
本发明公开了一种有机电致发光元件,所述元件具有顺序层合在发光层4一侧上的正极2和玻璃基质1,以及在所述发光层4另一侧上形成的负极5,所述元件具有功能层,所述功能层通过使至少一种选自染料和电荷传输材料的化合物的气体分子接触并渗透π共轭的有机高分子化合物而形成。
Description
技术领域
本发明涉及一种光亮且高效的电致发光元件,所述元件使具有电荷传输能力的低分子量化合物的气体分子渗透进π共轭的有机高分子化合物中,本发明还涉及所述元件的生产方法。
背景技术
近年来,大量的尝试已集中于开发利用有机化合物的电致发光元件,将其用于下一代平板显示器中。已经公开报道了具有双层结构的元件,其中将有机荧光染料用于发光层并且层合发光层和有机电荷传输化合物(例如日本特开昭59-194393号),以及利用高分子化合物作为荧光材料的元件(例如PCT专利申请WO 9013148,日本特开平3-244630号)。这些利用有机荧光材料的电致发光元件可以用低压直流驱动,并且除了高发光度外还可以容易地发出多种颜色的光。尤其是通过真空沉积法由低分子量化合物形成的层合薄膜可以用来配置高度可靠的彩色器件。但是,由上述方法配置的器件的缺点是成本高并且难以形成具有大面积的器件。
因此,提出了一种由薄膜形成的有机电致发光元件(高分子化合物电致发光元件),该薄膜通过使用以苯撑亚乙烯(phenylenevinylene)、噻吩、苯等作为基本骨架的共轭型高分子化合物来生产。除了主要是利用低分子量有机化合物的有机电致发光元件外,还提出了利用高分子化合物发光材料的高分子化合物LED,参见PCT专利申请WO9013148、日本特开平3-244630号、Appl.Phys.Lett.,第8卷,第1982页(1991年)等。PCT专利申请WO 9013148公开了通过在电极上形成可溶性前驱体薄膜并且热处理转化成共轭型高分子化合物来制备聚对苯撑乙炔(poly(p-phenylenevinylene))(PPV)薄膜,而且将该PPV用于元件的实例。
关于有机化合物薄膜的制备,日本特开2001-026884号描述了为了向树脂模制产品的表面上均匀地渗透并分散对树脂具有亲合力并且具有升华性质的有机化合物,将树脂模具和对树脂具有亲合力并且具有升华性质的有机化合物置于气密的容器中,并且调节该容器内部的压力和温度,使有机化合物处于饱和的升华压力的状态中,从而有机化合物蒸气均匀地粘附到树脂模具的表面上而且还渗透并分散入树脂模具中。
日本特开2001-003195号公开了修饰和/或着色树脂表面层的方法,从而通过将使对树脂具有亲合力并且具有升华性质的有机化合物均匀地渗透并分散入树脂模具的表面中而修饰和/或着色树脂表面层,其中将树脂模具和对树脂具有亲合力并且具有升华性质的有机化合物置于气密的容器中,并且调节内部的压力和温度,使有机化合物处于饱和的升华压力的状态中,从而促进有机化合物蒸气均匀地粘附到树脂模具的表面上,并且促进该有机化合物渗透并分散到整个树脂模具。
日本特开2000-281821号公开了修饰表面层以获得具有均匀厚度和组成的薄膜的方法,该方法通过能与目标物体相互作用的升华材料(sublimation material)修饰待涂布的目标物体表面层组合物,其中与目标物体表面层组合物相互作用的升华材料被置于密闭的空间中;调节该空间至升华材料的饱和升华压力状态;升华材料蒸气粘附到目标物体的表面层组合物上;并且粘附的升华材料从该表面层组合物的表面上进一步渗透并分散入表面层中,由此与表面层组合物相互作用。
但是,例如上述的未取代的π共轭有机高分子化合物的材料可加工性差,包括可掺杂性不好。因此,使用这些材料生产的电致发光元件具有相对差的发光度,并且发光的颜色仅局限于荧光的初始颜色。
发明内容
本发明通过控制包含冗共轭的有机高分子化合物的有机电致发光元件的发光颜色而有利地提高了发光度和发光效率。
为了提供上述的优点,本发明提供了包含兀共轭的有机高分子化合物的有机电致发光元件,该元件包括功能层,所述功能层通过使至少一种选自染料和电荷传输材料的化合物的气体分子接触并渗透冗共轭的有机高分子化合物中而形成。本发明的电荷传输材料是低分子量材料并且具有升华性质。除此之外,该材料给其非晶固态薄膜或分散体提供了向电介质高分子化合物基质(绝缘体)中传输电荷的能力。具有电荷传输能力的材料被分成传输正(+)电荷的空穴传输材料和传输负(-)电荷的电子传输材料。作为空穴传输材料,有具有咔唑环、噻吩环、三苯胺、三苯甲烷或二(distilbene)结构的低分子量化合物和被重氮基或叠氮基键合的所述低分子量化合物。作为电子传输材料,有具有二唑环、三唑环、醌环、咪唑环、黄酮环、噻唑环、苯并咪唑环、喹啉环、喹喔啉(quinozaline)环或吡嗪环的化合物和其中引入了硝基或氰基的前述化合物。还有具有发光能力的电子传输化合物,以及在配体中具有苯并二唑环、喹啉环、苯并喹啉环、苯并噻唑环或羟基黄酮环的铝、锌、铍、铕和铒的络合物。
而且,本发明的另一种电致发光元件以发光层和/或电荷传输层作为功能层。
附图说明
图1是根据本发明实施方式的高分子化合物电致发光元件的截面图;
图2是显示在实施例1的电致发光元件制造方法的一个阶段(至抽真空)中的光导制造设备轮廓的截面图;
图3是显示在实施例1的电致发光元件制造方法的一个阶段(至管的密封)中的光导制造设备轮廓的截面图;
图4是显示在实施例1的电致发光元件制造方法的一个阶段(密封所述管后)中的光导制造设备轮廓的截面图;
图5是显示在实施例1的电致发光元件制造方法的一个阶段(加热时)中的光导制造设备轮廓的截面图;
图6是显示在对比例1的电致发光元件制造方法的一个阶段(至抽真空)中的光导制造设备轮廓的截面图;
图7是显示在对比例1的电致发光元件制造方法的一个阶段(密封所述管后)中的光导制造设备轮廓的截面图;
图8是显示在对比例1的电致发光元件制造方法的一个阶段(加热时)中的光导制造设备轮廓的截面图;和
图9是显示根据实施例的电致发光元件制造方法的光导制造设备轮廓的截面图。
具体实施方式
参照附图说明本发明优选的实施方式。图1显示了本发明的高分子化合物电致发光元件的一个实施方式的截面图。如图1所示,本实施方式的高分子化合物电致发光元件具有顺序层合在发光层4一侧上的空穴注入层3和的正极2,以及层合在正极2另一侧上的玻璃基质1。同时,在发光层4的另一侧上形成负极5。
对于发光层4,使用通过施加电压而具备电荷传输能力并且发光的共轭型高分子化合物。共轭型高分子化合物的实例包括π共轭的有机高分子化合物,其具有由通式-(Ar)n-和/或-(ArA)n-表示的化学结构,其中Ar表示苯环、噻吩环、吡啶环、吡咯环或者二唑环,并且A表示双键、三键或者NH键,并且其具体的实例有包含苯撑乙炔或芴作为结构单元的高分子化合物材料。当使用聚对苯撑乙炔(PPV)作为共轭型高分子化合物时,获得530至570纳米的黄绿色发光。
下面将描述根据本实施方式的高分子化合物电致发光元件制造方法的实例。将未取代的π共轭高分子化合物,例如PPV前驱体(聚对二甲苯氯化噻吩)(poly(p-xylenethiopheniumchloride))溶液施加到玻璃基质1上,该玻璃基质1上通过溅射形成有500纳米厚的ITO薄膜,然后煅烧以形成PPV膜。然后,向该PPV膜上一起沉积银和镁,以层合负极5,从而生产出电致发光元件。结果是该PPV膜的电子传输能力低于空穴传输能力,并且发光度和发光效率不足。此外,因为PPV是不溶且不熔的,所以不可能进行掺杂。但是,发现通过将层合有负极的PPV薄膜放入玻璃管中,将2-(4-联苯基)-5-(4-叔丁苯基)-1,3,4-二唑(2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole)(PBD)作为电子传输化合物置于上述管中;排空并将该管密封入安瓿中,并且热处理该安瓿,获得具有渗透的PBD的PPV层薄膜。除此之外,发现在渗透过程后通过在具有负极的PPV薄膜上一起沉积银和镁,具有负极5层合的电致发光元件具有明显的电子传输和改善的发光度。
电荷传输化合物、荧光染料等渗透入不溶且不熔的PPV中的具体机理尚不清楚,但是推测因为电荷传输化合物和荧光染料在玻璃管内升华,所以该化合物分解成分子水平并且渗透通过PPV薄膜的细隙。
除了上述PPV外,聚噻吩、聚噻吩乙炔(polythiophenevinylene)、对聚苯(poly(p-phenylene))、聚对苯基乙炔(poly(p-phenylacetylene))等可以用作具有电荷传输能力的发光层4。
空穴注入层3适当地在电致发光元件的正极2上形成。空穴注入层的优选材料的实例包括含聚苯乙烯磺酸的聚(乙烯二氧噻吩)(polystyrene sulfonic acid-containing poly(ethylene dioxythiophene)(PEDOT-PSS)和由化学式I表示的PTPDES;由化学式II表示的Et-PTPDEK和由化学式III表示的PBBA;以及作为低分子量化合物的铜酞菁和由化学式IV表示的TBPAH。
适当地在发光层4和空穴注入层3之间插入空穴传输层,并且使用聚苯胺、聚噻吩、聚吡咯、聚噻吩乙炔及其衍生物。当使用未取代的π共轭高分子化合物作为空穴传输层时,因为类似地其不溶且不熔,所以可以通过上述方法渗透空穴传输化合物。因此,可以生产具有更好效率的空穴传输层。上述空穴传输材料可以用作渗透化合物。
用于空穴传输层的具有发光能力的π共轭高分子化合物的电子传输能力低于空穴传输能力,从而不仅PBD,而且上述的电子传输材料和具有发光能力的电子传输材料都可以作为提高电子传输能力的低分子量化合物而用作渗透化合物。
根据本发明,不仅通过使用具有电荷传输能力的化合物,而且通过使用具有发光能力的π共轭高分子化合物的荧光染料作为用于空穴传输层的化合物,可以控制发光颜色。例如,当PPV的发光是峰值为550纳米的绿光时,发光峰在550纳米长波长侧的荧光染料可以改变荧光颜色。可以使用荧光染料包括香豆素型、喹吖啶酮型、二氰基亚甲基(dicyanomethylene)型、二氰基二氮杂(dicyanodiazepine)型、苯并噻唑型、苝型、乙腈-三苯胺型、含铕原子络合物型和氮杂苯并蒽(azabenzoanthracene)-吡喃型染料。
实施例
下面将参照附图描述本发明的实施例。应该理解本发明并不局限于下面的实施例。
实施例1
如图2所示,举例来说将100毫克电子传输化合物2-(4-联苯基)-5-(4-叔丁苯基)-1,3,4-二唑(PBD)作为具有蒸气压的有机化合物20置于一端封闭的玻璃管10(例如外径15毫米、内径12毫米)内的一端。然后,将在具有ITO电极的玻璃基质上形成的PPV树脂薄膜30(1毫米厚、8毫米宽、40毫米长)置于玻璃管的中部。玻璃管10的开口端与抽空装置50连接以进行抽空,然后如图3所示,使用玻璃管密封燃烧器60熔化与该抽空装置50相连的玻璃管10的接近开口端的部分。因此,将有机化合物20和树脂薄膜30密封在玻璃管11中,如图4所示。在密封后,如图5所示将密封的玻璃管11置于恒温室70中,在内部温度维持在120℃的恒温室70中保持1小时,然后在1小时内缓慢冷却至室温。切断玻璃管11,移出其中已经渗透并分散有有机化合物20的树脂薄膜30。然后,一起沉积银和镁,以层合负极,由此生产出电致发光元件。该电致发光元件发射黄绿色光并且在14V下最大发光度为3000c d/m2。外部量子效率为3.21m/w。
考虑要开发显示监视器,发光度必须大约为1000c d或更高,但是发光度根据像素的精细度(fineness)可变。如果发光度低于1000c d,不能在室内环境下(在荧光灯下)识别图像。当外部量子效率为1.0lm/w或更小时,能耗大,并且常规电池可能在只发光几分钟内就耗尽,而且发热量高达可能会损伤元件本身。上面和后面实施例中使用的“1m/w”意指“流明/瓦特”(lumen/watt)。
对比例1
为了确定实施例1中2-(4-联苯基)-5-(4-叔丁苯基)-1,3,4-二唑(PBD)的效果,如下进行在具有ITO电极的玻璃基质上形成的PPV树脂薄膜31(1毫米厚、8毫米宽、40毫米长)的加热对比实验。具体地说,如图6所示,仅将在具有ITO电极的玻璃基质上形成的PPV树脂薄膜31置于外径15毫米、内径12毫米、长200毫米的一端封闭的玻璃管12中。玻璃管12的开口端与抽空装置51连接以进行抽空。然后,通过玻璃管密封燃烧器61熔化并密封与该抽空装置51相连的玻璃管12的接近其开口端的部分,从而将树脂薄膜密封在密封的玻璃管12中,如图7所示。将密封的玻璃管12置于恒温室71中,在恒温室71的内部温度维持在120℃时保持24小时,然后缓慢冷却至室温。冷却后,切断玻璃管12,取出热处理过的在具有ITO电极的玻璃基质上形成的PPV树脂薄膜31。然后,一起沉积银和镁以层合负极,从而生产出电致发光元件。所制造的电致发光元件发射黄绿色光并且在14V下最大发光度为20c d/m2,外部量子效率为0.71m/w。对比例2
除了使用全氟辛烷代替PBD外,按照与实施例1相同的方式,将在具有ITO电极的玻璃基质上形成的PPV树脂薄膜密封于玻璃管中、加热并缓慢冷却。测量所得PPV树脂薄膜的紫外、可见和红外吸收光谱,未识别出源于全氟辛烷的吸收。这些结果证明全氟辛烷对PPV树脂薄膜没有亲合力,因此不会渗透并分散入树脂薄膜板内。
从实施例1和对比例1和2中发现当在减压密封的玻璃管中通过加热蒸发有机化合物时,玻璃管填充蒸气,并且当蒸气保持在加热状态而不冷却并且将对有机化合物具有亲合力的树脂薄膜置于该蒸气中时,可以产生所需功能的有机分子被分散在树脂薄膜内。
实施例2
如图2所示,作为具有蒸气压的有机化合物20,将100毫克有机显色荧光染料4-(二氰基甲基)-2-甲基-6-(4-二甲基氨基苯乙烯基)-4-H-吡喃(4-(dicyanomethyl)-2-methyl-6-(4-dimethylaminostyryl)-4-H-pyran)(DCM)置于一端封闭的外径15毫米且内径12毫米的玻璃管10的一端。然后,将在具有ITO电极的玻璃基质上形成的PPV树脂薄膜30(1毫米厚、8毫米宽、40毫米长)置于玻璃管的中部。玻璃管10的开口端与抽空装置50连接以进行抽空,然后如图3所示,使用玻璃管密封燃烧器60熔化与该抽空装置50相连的玻璃管10的接近开口端的部分以进行密封。因此,将有机化合物20和树脂薄膜30密封在密封的玻璃管11中,如图4所示。在密封后,如图5所示将密封的玻璃管11置于恒温室70中,在内部温度维持在120℃的恒温室70中保持1小时,然后在1小时内缓慢冷却至室温。冷却后,切断玻璃管11,取出已经在其中渗透并分散有有机化合物20的PPV。然后,一起沉积银和镁以层合负极,从而生产出电致发光元件。该电致发光元件发射桔黄色光并且在14V下最大发光度为2000c d/m2。外部量子效率为4.11m/w。
实施例3
图9是显示本实施例中使用的电致发光元件制造设备示意结构的截面图。使用具有PPV的树脂薄膜300,该薄膜通过在具有ITO的玻璃基质上形成PEDOT-PSS膜、向其上施加聚(对二甲苯氯化噻吩溶液并且煅烧而形成。同时,制备放置了PBT的升华源240(5毫米厚、10毫米宽、400毫米长)。将具有ITO的PEDOT-PSS/PPV树脂薄膜300放入气密性的容器110中,并且在另一个气密性的容器120中放入升华源240。两个气密性的容器110、120通过管道和阀195互相连接。放置具有ITO的PEDOT-PSS/PPV树脂薄膜300的气密性容器110具有不锈钢或铝外壁和为了装载和卸载树脂薄膜300而分成上部和下部的结构(未示出)。
气密性容器110的内部100通过真空阀190和抽空管道系统130与抽空系统150连接,并且排气,使室温下气密性容器110的内部压力为10-4帕斯卡或更低,并且关闭真空阀190。因此,密封气密性容器110。
作为加热装置,可以使用升华源基质加热器410、树脂薄膜棒状加热器400以及由铝形成的例如具有真空规格包埋的外鞘电加热线的真空阀加热器790。通过由热传导性质好的材料制成的加热器均匀地加热气密性容器110的内部100和真空阀190,并且处理后不留下任何缝隙。
在本实施例中,气密性容器110的内部100被减压,并且使用如上所述的升华源基质加热器410进行加热,以控制整体的温度至预设的温度(例如当PBD用作蒸发源240时为150℃)。按照相同的方式,还将具有气密性密封蒸发源的气密性容器120加热至高于其中放置了具有ITO的PEDOT-PSS/PPV树脂薄膜300的气密性容器110预设温度的温度(在此情况下为155℃)。然后,打开连接两个气密性容器110和120的阀195,并且维持每个容器内设定的温度30分钟。然后,将气密性容器110和120内的温度缓慢降低至25℃。然后,恢复气密性容器110的内部100至大气压,并且取出其中渗透并分散有PBD的PEDOT-PSS/PPV树脂薄膜300。一起沉积银和镁以层合负极,从而生产出电致发光元件。该电致发光元件发射桔黄色光并且在14V下最大发光度为4500c d/m2。外部量子效率为4.81m/w。
如上所述,因为使用升华或挥发性的电荷传输有机化合物和荧光染料代替例如掺杂的过程,并且以气体分子接触以使其渗透从而包含在π共轭的有机高分子化合物中,所以本发明的电致发光元件在π共轭的有机高分子化合物中完全并且可靠地不含杂质。另外,因为在本发明方法制造的电致发光元件中,通过以气体分子接触并且渗透而可以在π共轭的有机高分子化合物中包含升华或挥发性的电荷传输有机化合物和荧光染料,所以不可能在π共轭的有机高分子化合物中含有杂质。因此,可以生产出由不可能包含杂质的π共轭的有机高分子化合物形成的有机薄膜。结果,可以高效地生产具有高发光效率并且能够发出可改变的或者改变颜色的光的电致发光元件。
工业应用性
如上详细所述,本发明提供了具有高发光效率并且能够改变发光颜色的电致发光元件。
Claims (13)
1.包含未取代的π共轭的有机高分子化合物的有机电致发光元件,其包括功能层,所述功能层通过使至少一种选自染料和电荷传输材料的化合物的气体分子接触并渗透所述未取代的π共轭的有机高分子化合物而形成。
2.包含未取代的π共轭的有机高分子化合物的有机电致发光元件,其包括发光层,所述发光层通过使至少一种选自染料和电荷传输材料的化合物的气体分子接触并渗透所述未取代的π共轭的有机高分子化合物而形成。
3.包含未取代的π共轭的有机高分子化合物的有机电致发光元件,其包括电荷传输层,所述电荷传输层通过使至少一种选自染料和电荷传输材料的化合物的气体分子接触并渗透所述未取代的π共轭的有机高分子化合物而形成。
4.如权利要求1至3任何一项所述的有机电致发光元件,其中所述未取代的π共轭的有机高分子化合物具有由通式-(Ar)n-和/或-(ArA)n-表示的化学结构,其中Ar表示苯环、噻吩环、吡啶环、吡咯环或者噁二唑环,并且A表示双键、三键或者NH键。
5.如权利要求1至3任何一项所述的有机电致发光元件,其中所述未取代的π共轭的有机高分子化合物是至少一种选自聚对苯撑乙炔、聚噻吩、聚噻吩乙炔、对聚苯和聚对苯基乙炔的物质。
6.如权利要求1至3任何一项所述的有机电致发光元件,其中所述染料是荧光染料。
7.如权利要求6所述的有机电致发光元件,其中所述荧光染料是至少一种选自香豆素型染料、喹吖啶酮型染料、二氰基亚甲基型染料、二氰基氮杂型染料、苯并噻唑型染料、型染料、乙腈-三苯胺型染料、含铕原子络合物型染料和氮杂苯并蒽-吡喃型染料的染料。
8.如权利要求1至3任何一项所述的有机电致发光元件,其中所述电荷传输材料是至少一种选自传输正(+)电荷的空穴传输材料、传输负(-)电荷的电子传输材料和具有发光能力的电子传输化合物的化合物。
9.如权利要求8所述的有机电致发光元件,其中所述空穴传输材料是至少一种选自具有咔唑环、噻吩环、三苯胺、三苯甲烷或二芪结构的低分子量化合物和被重氮基或叠氮基键合的所述低分子量化合物的空穴传输材料。
10.如权利要求8所述的有机电致发光元件,其中所述电子传输材料是至少一种选自具有噁二唑环、三唑环、醌环、咪唑环、黄酮环、噻唑环、苯并咪唑环、喹啉环、喹喔啉环或吡嗪环的化合物和其中引入了硝基或氰基的前述化合物的电子传输材料。
11.如权利要求8所述的有机电致发光元件,其中所述具有发光能力的电子传输化合物是至少一种选自配体中具有苯并噁二唑环、喹啉环、苯并喹啉环、苯并噻唑环或羟基黄酮环的铝、锌、铍、铕和铒的络合物的化合物。
12.包含未取代的π共轭的有机高分子化合物的有机电致发光元件,其包括发光层和电荷传输层,所述发光层和电荷传输层通过使至少一种选自染料和电荷传输材料的化合物的气体分子接触并渗透所述未取代的π共轭的有机高分子化合物而形成。
13.有机电致发光元件的制备方法,其包括加热未取代的π共轭的有机高分子化合物;并使至少一种选自染料和电荷传输材料的化合物的气体分子接触并渗透所述未取代的π共轭的有机高分子化合物。
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US20070072000A1 (en) | 2007-03-29 |
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TWI390750B (zh) | 2013-03-21 |
GB0605822D0 (en) | 2006-05-03 |
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US20110081478A1 (en) | 2011-04-07 |
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