CN1504534A - 使用二聚二甲苯一羧酸的有机发光器件 - Google Patents
使用二聚二甲苯一羧酸的有机发光器件 Download PDFInfo
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- CN1504534A CN1504534A CNA200310119723A CN200310119723A CN1504534A CN 1504534 A CN1504534 A CN 1504534A CN A200310119723 A CNA200310119723 A CN A200310119723A CN 200310119723 A CN200310119723 A CN 200310119723A CN 1504534 A CN1504534 A CN 1504534A
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
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Abstract
一种有机发光器件(OLED),其中使用二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物作为发射层和/或一个或多个电荷迁移层,或者作为用于一个或多个这些层的主体材料。
Description
发明背景
发明领域
本发明涉及一种有机发光器件(OLED),其中使用二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物作为发射层和/或一个或多个电荷迁移层,或者作为用于一个或多个所述层的主体材料。
现有技术描述
人们已经努力进行有效的尝试,以发展适用于有机发光器件(OLED)的材料。所述器件是具有市场吸引力的,因为它们为具有长寿命和宽色彩范围,显示出明亮的电致发光的高密度像素显示器提供了低廉的制造成本。
OLED通常是通过将发射层夹在阳极和阴极之间而制成的。当施加偏流通过电极时,空穴和电子分别由阳极和阴极注入发射层,通常被临近各电极的空穴迁移和电子迁移层推动。空穴和电子在发射层辐射重组并发光。如果提供阻断层以阻断空穴或电子由相邻层注入及其从器件中随后逃逸,那么就能够使性能得以改善。可以将这些层中的一些合并起来。例如,由合并的空穴注入和迁移层,以及合并的电子迁移和发光层制成一个双层结构。类似地,空穴注入和迁移层、发光层和电子注入和迁移层组成了一个三层结构。
此外,可以在主体材料中掺入能够实现所需层效果的另一种材料(例如,为了实现空穴迁移效果、电子迁移效果或发光效果),以形成这些层。
因为消费者期望OLED具有良好效率、长使用寿命和纯的色度,因此存在发展适用于各种层的材料的需要。
发明概述
本发明的目的是提供一种改进的OLED,其中使用二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物作为发射层和/或一个或多个电荷迁移层,或者作为用于一种或多种所述层的主体材料。
因此,本发明一方面涉及一种OLED,其中发射层夹在至少阴极和阳极之间,并且其中发射层包括以下通式(I)所示的二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物:
其中,Ar表示任选地存在的芳族基团,其中R1-R8任选地存在,并且其中R1-R8各自独立地表示氢原子、卤原子、羟基、取代或未取代的氨基、硝基或氰基、取代或未取代的烷基、取代或未取代的链烯基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳烃基、取代或未取代的芳族杂环基、取代或未取代的芳烷基、取代或未取代的芳氧基或者取代或未取代的烷氧羰基或羧基。
优选Ar芳基不存在,但如果存在,可以是对位键连或邻位键连的基团。
式(I)所示的化合物可以直接用作发射层,或者在发射层含有二聚二甲苯一羧酸主体加上发射掺杂剂的情况下,作为用于发射掺杂剂的主体材料。
另一方面,本发明的器件是一种在至少一个电荷迁移层与阳极和阴极之间夹有发射层的OLED。电荷迁移层可以是电子迁移层或空穴迁移层,或以上二者。根据本发明的这一方面,电荷迁移层包括以上通式(I)的二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物,其中Ar和R1-R8定义同上。
根据这一方面,通式(I)所示的化合物可以直接用作电荷迁移层,或者在电荷迁移层含有主体材料加上电荷迁移掺杂剂的情况下,形成电荷迁移主体材料。
提供该概述是为了更快地理解本发明的特征。结合附图,参照以下优选实施方案的详细描述,可以更充分地理解本发明。
附图简要说明
图1是薄膜态的具有化合物(IV)的OLED的光致发光图谱。
图2是本发明OLED的横截面示意图。
发明详述
二聚二甲苯一羧酸和二聚二甲苯一羧酸衍生物具有以下通式:
在上式(I)中,R1、R2、R3、R4、R5、R6、R7和R8可以是取代或未取代的,这取决于在其合成中使用的原料,或欲实现的终产物的所需特性。取代基可以包括但不限于,氢原子、卤原子、羟基、取代或未取代的氨基、硝基或氰基、取代或未取代的烷基、取代或未取代的链烯基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳烃基、取代或未取代的芳族杂环基、取代或未取代的芳烷基、取代或未取代的芳氧基或者取代或未取代的烷氧羰基或羧基。
此外,在上式(I)中,Ar表示任选地存在的芳基。
适合本发明使用或作为制备本发明衍生物的原料的二聚二甲苯一羧酸材料可以使用本领域已知的方法制备。这些方法包括但不限于,在Chemical Reviews,Vol.95,No.7,2457-2483(1995)中公开的Suzuki偶合反应,此处引作参考;在Journal of the AmericanChemical Society,Vol.91,No.13,3527-3533(1969)中公开的步骤,此处引作参考;以及在Journal of the American Chemical Society,Vol.109,No.9,2631-39(1987)中公开的相关步骤,此处也引作参考。
本发明公开的用于OLED的二聚二甲苯一羧酸的一个优点在于,这些化合物显示出优异的光致发光量子效率。此外,由于其刚性的环状结构,预期二聚二甲苯一羧酸材料可以称为良好的主体,用于小分子化合物或金属。因此,预计二聚二甲苯一羧酸材料可以显示出优异的发射、电子迁移和空穴迁移能力。此外,由于这些特性,预期作为主体用于功能材料的二聚二甲苯一羧酸材料可以导致OLED的性能得以增强。
用于OLED制备的通用步骤如下:
1)获得覆盖了图形层的干净的ITO底物。
2)用O2等离子体处理底物1-5分钟。
3)将底物置于热蒸发器中并将压力压低至6×10-6torr。
4)将有机和金属层蒸发到底物上。
a.空穴迁移层蒸发为200的厚度。
b.通常用主体和掺杂剂蒸发出发射层。通过关闭光闸,以防止早期沉积,掺杂剂的蒸发稳定在约0.03/s的速率。随后,主体的蒸发稳定在约1-3/s的速率,得到的掺杂浓度为约1-3%。随后开启光闸,并通过石英晶体计量器计量沉积作用。发射层通常沉积为100-400。
c.以约1-3/s的速率蒸发电子迁移材料,以形成厚度通常为200-400的层。
d.将掩模邻近底物放置,以确定金属电极蒸发的位置。
e.蒸发约120的Li-Al合金,以改善电子向器件中的注入。
f.沉积约1500的Al,并将蒸发器冷却。
5)对器件进行亮度、色度和电流-电压特征的检测。
在本发明中,可以作为主体材料、电荷迁移体、空穴迁移体和发射体的式(I)所示二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物的一些具体例子包括以下的化合物。此外,这些化合物全部是对称的,其中,如果R1存在,那么R7也是存在的,并且相同;如果R2存在,那么R8也是存在的,并且相同;如果R1和R5存在,那么R3和R7也是存在的,并且相同;以及如果R2和R6存在,那么R4和R8也是存在的,并且相同。
实施例1-6显示了一些代表性二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物,包括非对称结构的合成。
实施例1
参照Journal of the American Chemical Society,Vol.91,No.13,3527-3533(1969),以及Journal of the American Chemical Society,Vol.109,No.9,2631-39(1987)中公开的步骤,合成化合物(I)。使用上述通用步骤,将化合物(I)制成OLED。
实施例2
按照实施例1所述的类似方式,参照Journal of the AmericanChemical Society,Vol.91,No.13,3527-3533(1969),以及Journal ofthe American Chemical Society,Vol.109,No.9,2631-39(1987)中公开的步骤,合成化合物(II)。使用上述通用步骤,将化合物(II)制成OLED。
实施例3
使用Suzuki偶合反应合成化合物(III)。在化合物(III)的合成中,在圆底烧瓶中装入假-间二溴-[2,2]二聚二甲苯一羧酸(0.26g,0.71mmol)、4-硼酸联苯(0.43g,2.2mmol)、Pd(O)(PPh3)4(100mg),以及20ml干燥甲苯和10ml干燥乙醇的混合物。在室温下搅拌10分钟后,向反应溶液中加入Na2CO3的2M脱气水溶液10ml。在N2下于80℃搅拌反应混合物2天。冷却后,将混合物倾入水中。产物用甲苯萃取、用水洗涤并经MgSO4干燥。过滤并浓缩后,通过柱色谱法(硅胶,CH2Cl2/己烷混合物)纯化。使用上述通用步骤,将化合物(III)制成OLED。
实施例4
按照实施例3所述的类似方式反应合成化合物(IV),使用9,9-二甲基-2-硼酸芴代替4-硼酸联苯。使用上述通用步骤,将化合物(IV)制成OLED。器件在其薄膜状态下发射出明亮的蓝光。使用薄膜状态的化合物(IV)的器件的光致发光(PL)图谱见图1所示。
实施例5
使用Suzuki偶合反应合成化合物(V)。在化合物(V)的合成中,向4,7,12,15-四溴[2,2]二聚二甲苯一羧酸(0.4g,0.76mmol)和11,12-二亚甲基-9,10-二氢-9,10-桥亚乙基蒽(0.38g,1.65mmol)于30ml干燥甲苯的溶液中滴加n-BuLi(1.6ml,2.5mmol,1.6M于己烷中)。在N2下将溶液搅拌过夜,并用少量水淬灭。有机层用甲苯萃取,用水洗涤并经MgSO4干燥。在除去溶剂后,从CH2Cl2中将产物重结晶出来。使用上述通用步骤,将化合物(V)制成OLED。
实施例6
使用Suzuki偶合反应合成化合物(VI)。在化合物(VI)的合成中,向烧瓶中加入化合物(V)(0.2g)、0.1g 0.5%的Pd/C和30ml邻二甲苯。溶液在氮气下回流2天。过滤热溶液,并在蒸馏除去溶剂后得到化合物(VI)。使用上述通用步骤,将化合物(VI)制成OLED。
实施例7
图1示意性地描述了本发明的OLED,其包括透明底物1、紧邻底物的阳极2、紧邻阳极的空穴迁移层3、发射层4、电子迁移层5和阴极6。这些层本身分别含有具有类似组成或功能的多个层。
适合用于底物1的材料包括玻璃、石英等,以及聚合物(包括但不限于聚酯、聚碳酸酯、聚丙烯酸酯、聚甲基丙烯酸酯和聚砜)。底物的厚度并不严格,可以在,例如约25-超过1000微米的范围内,这取决于器件的结构要求。
紧邻底物的阳极2可以由金属、合金、导电化合物或其混合物构成,特别是功函等于或大于约4电子伏特的上述材料。阳极的特定例子包括正电荷注入电极,诸如氧化铟锡(ITO)、氧化锡、氧化锌、金、铂、导电的碳和共轭聚合物,诸如聚苯胺、聚吡咯等。优选ITO。阳极的厚度可以在约10纳米-1微米的范围内任意变化。
空穴注入层3(此处也称为空穴迁移层)可以由一种或多种本领域已知的空穴迁移组分组成。任何能够将空穴注入和迁移至发射层的常规已知材料均可用以形成空穴注入层。优选的空穴注入和空穴迁移材料是具有以下结构的4,4’-双[N-(1-萘基-1)-N-苯基氨基]联苯(NPB):
NPB:4,4’-双[N-(1-萘基-1)-N-苯基氨基]联苯
发射层4可以是沉积的纯净物质。可用于本发明的一种适合的发射材料是蓝光发射体。蓝光发射体的合成是通过以下反应序列:
1)
2,7-二碘二甲基芴的合成
2)
蓝光发射体的合成
使用Suzuki偶合反应合成蓝光发射体。在该蓝光发射体的合成中,向Pd(dba)2(72mg,0.125mmol)于10ml甲苯的溶液中加入76mg三(叔丁基)膦于3ml甲苯的溶液,然后在氮气下搅拌30分钟。向暗褐色催化剂溶液中加入溶于20ml甲苯的2,7-二碘二甲基芴(360mg,0.564mmol)。将溶液搅拌约20分钟后,加入固体形式的217mg(2.26mmol)叔丁醇钠。在油浴中于80℃加热溶液5小时。接着,用水淬灭反应。然后用甲苯和乙酸乙酯萃取水相。有机相随后经MgSO4干燥,并接着蒸发溶剂。通过硅胶柱色谱法分离产物,并用正己烷和甲苯的2∶1(或3∶1)混合物洗脱,得到浅黄色固体。如果需要,可以通过再次的硅胶柱色谱法或重结晶进一步纯化产物。
在用于上述蓝光发射体合成的2,7-二碘二甲基芴的合成中,向20ml乙酸中的2FL(350mg,0.907mmol)、164mg(0.72mmol)H5I6O6-H2O和366mg I2(2.88mmol)中加入H2SO4(6ml)和H2O(4ml)的混合物。于80℃下搅拌溶液3小时,得到浅红色溶液。将溶液冷却至室温后,加入水。过滤沉淀的固体,随后用水和正己烷洗涤沉淀。随后将产物真空干燥,得到浅红色固体。如果通过硅胶柱纯化,浅红色被脱去。
发射层4也可以是客体-主体体系。适用于本发明的一个主体材料是9,9-二甲基芴-2-硼酸,其可以按照以下方式合成:
9,9-二甲基芴-2-硼酸的合成
使用Suzuki偶合反应合成9,9-二甲基芴-2-硼酸。在9,9-二甲基芴-2-硼酸的合成中,在氮气中,于-78℃的干冰-丙酮浴中,向溶于170ml乙醚的2-碘二甲基芴(16g,50mmol)的溶液中加入15%正丁基锂-己烷溶液(35.6ml,55mmol)。在搅拌淤浆溶液2.5小时后,将反应混合物温热至室温,随后继续搅拌1小时。于-78℃的冷浴中再次冷却溶液。随后向溶液中加入硼酸三甲酯(27.4ml,0.240mmol)。溶液在低温下搅拌1小时,并在室温下搅拌1小时。得到的反应混合物在室温下静置过夜。随后蒸除一半溶剂,然后加入50ml水。同时连续加入2M的HCl水溶液140ml。过滤沉淀并用甲苯洗涤。从有机相中除去溶剂,得到额外的硼酸。再用甲苯洗涤固体。随后在真空中干燥产物。
在客体-主体体系中,可以由掺有能够实现所需层效果的另一种材料(例如,为了实现空穴迁移效果、电子迁移效果或发光效果)的主体材料形成发射层4。一种适用于本发明的掺杂剂是双(二甲基芴),其可以按照以下方式合成:
双(二甲基芴)的合成
使用Suzuki偶合反应合成双(二甲基芴)。在双(二甲基芴)的合成中,将2-碘二甲基芴(1.98g,6.18mmol)和1.5g(4.73mmol)二甲基芴-2-硼酸溶于脱气甲苯(80ml)和脱气乙醇(40ml)的混合物中。向溶液中加入碳酸钠水溶液(41ml),然后在室温下搅拌30分钟,所述碳酸钠水溶液是将9g碳酸钠溶于45ml水而制成的。向所得的混浊溶液中加入238mg(0.206mmol)Pd(PPh3)4固体。随后在80℃油浴中,于氮气流下加热溶液5小时。冷却至室温后,向反应混合物中加入乙酸乙酯和水。分离有机相和水相。用甲苯和乙酸乙酯萃取水相。合并的有机相经MgSO4干燥,并蒸发溶剂。通过硅胶柱色谱法分离所需产物,并用正己烷和甲苯的2∶1(或3∶1)混合物洗脱,得到白色,浅黄色固体。如果需要,可以通过再次的硅胶柱色谱法或重结晶进一步纯化产物。
电荷迁移层5含有电荷迁移材料。在电荷迁移能力也结合至基于二聚二甲苯一羧酸物质的发射层4的情况下,电荷迁移层是任选的。任何已知的电荷迁移材料均可作为任选的电荷迁移层使用。AlQ型材料,诸如三(8-羟基喹啉)铝及其衍生物特别优选。一个优选的电荷迁移材料是具有以下结构的4,7-二苯基-1,10-菲咯啉(Bphen):
4,7-二苯基-1,10-菲咯啉(Bphen)
阴极6可以由任何金属,包括高或低功函的金属组成。铝、锂、镁和钙特别优选。
再次参照图2的参考数字,通过以下步骤制备本发明的OLED:首先在异丙醇中将玻璃底物1清洗5分钟,所述底物上具有ITO阳极2图样,然后在去离子水中洗涤5分钟,并在异丙醇中再清洗5分钟。用O2等离子体处理清洁后的ITO底物,并将其置于热蒸发器中,其中压力下降至6×10-2Torr。加热NPB层,并以1-3nm/秒的速度,通过真空沉积,将其沉积为厚度20nm的空穴注入层3。接着,以3nm/秒的速度,通过真空沉积,将化合物(II)和02wt%的蓝光发射体沉积为厚度30nm的发射层4,并且加入9,9-二甲基芴-2-硼酸作为主体,加入双(二甲基芴)作为蓝光掺杂剂。通过真空沉积,将Bphen沉积为厚度20nm的电子迁移层5。最后,施加含有Li-Al层(12nm),然后是Al层(150nm)的双层阴极6,以改善OLED中的电子注入。施加驱动电压并观测均匀的蓝光色度。7V下器件产生的电流密度是200mA/cm2。7V下器件产生的发光度是1000cd/m2。最大外量子效率是7%,最大外功率是0.4lm/W。CIE色坐标是(0.18,0.11)。
上述实施例仅用于阐述,而不应认为是对发明的限制,本发明的范围是由以下权利要求定义的,并认为其包含的各种变型和改进对于本领域技术人员是显而易见的。
Claims (16)
2.权利要求1的有机发光器件,其中如果Ar基团存在,它们是对位键连的。
3.权利要求1的有机发光器件,其中如果Ar基团存在,它们是邻位键连的。
4.权利要求1的有机发光器件,其中所述发射层由二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物的功能发光层组成。
5.权利要求1的有机发光器件,其中所述发射层由二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物的主体材料,以及功能发光掺杂剂组成。
6.权利要求1的有机发光器件,其中对称地提供R1-R8。
7.权利要求1的有机发光器件,其中非对称地提供R1-R8。
9.权利要求8的有机发光器件,其中如果Ar基团存在,它们是对位键连的。
10.权利要求8的有机发光器件,其中如果Ar基团存在,它们是邻位键连的。
11.权利要求8的有机发光器件,其中所述电荷迁移层由二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物的功能电荷迁移层组成。
12.权利要求8的有机发光器件,其中所述电荷迁移层由二聚二甲苯一羧酸或二聚二甲苯一羧酸衍生物的主体材料,以及功能电荷迁移掺杂剂组成。
13.权利要求8的有机发光器件,其中电荷迁移层是电子迁移层。
14.权利要求8的有机发光器件,其中电荷迁移层是空穴迁移层。
15.权利要求8的有机发光器件,其中对称地提供R1-R8。
16.权利要求8的有机发光器件,其中非对称地提供R1-R8。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/309,116 US6869698B2 (en) | 2002-12-04 | 2002-12-04 | Organic light-emitting device using paracyclophane |
US10/309,116 | 2002-12-04 |
Publications (1)
Publication Number | Publication Date |
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CN1504534A true CN1504534A (zh) | 2004-06-16 |
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Application Number | Title | Priority Date | Filing Date |
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CNA200310119723A Pending CN1504534A (zh) | 2002-12-04 | 2003-12-03 | 使用二聚二甲苯一羧酸的有机发光器件 |
Country Status (3)
Country | Link |
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US (1) | US6869698B2 (zh) |
JP (1) | JP2004186158A (zh) |
CN (1) | CN1504534A (zh) |
Cited By (1)
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CN101577315B (zh) * | 2004-12-06 | 2012-08-01 | 株式会社半导体能源研究所 | 电子设备以及发光器件 |
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JP4035499B2 (ja) * | 2003-10-08 | 2008-01-23 | キヤノン株式会社 | 有機発光素子 |
US7462750B2 (en) * | 2005-10-31 | 2008-12-09 | Specialty Coating Systems, Inc. | Parylene variants and methods of synthesis and use |
US7994372B2 (en) * | 2005-10-31 | 2011-08-09 | Specialty Coating Systems, Inc. | Parylene variants and methods of synthesis and use |
US7652178B2 (en) * | 2007-02-26 | 2010-01-26 | Specialty Coating Systems, Inc. | Perfluoroparacyclophane and methods of synthesis and use thereof |
US8945307B2 (en) | 2009-12-23 | 2015-02-03 | Aeroquest Research Group Llc | Apparatus and method for vapor deposition of dielectric wire coating |
DE102010002482B3 (de) | 2010-03-01 | 2012-01-05 | Technische Universität Braunschweig | Lumineszente Organometallverbindung |
ES2952036T3 (es) | 2013-06-12 | 2023-10-26 | Rohinni Inc | Teclado de retroiluminación con fuentes generadoras de luz depositadas |
KR101607594B1 (ko) * | 2015-02-03 | 2016-03-30 | 한국과학기술연구원 | 전도성 유기 반도체 화합물을 포함하는 유무기 하이브리드 광전변환 소자 및 이의 제조방법 |
US10629393B2 (en) | 2016-01-15 | 2020-04-21 | Rohinni, LLC | Apparatus and method of backlighting through a cover on the apparatus |
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-
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- 2003-12-02 JP JP2003403751A patent/JP2004186158A/ja not_active Withdrawn
- 2003-12-03 CN CNA200310119723A patent/CN1504534A/zh active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101577315B (zh) * | 2004-12-06 | 2012-08-01 | 株式会社半导体能源研究所 | 电子设备以及发光器件 |
Also Published As
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US20040110027A1 (en) | 2004-06-10 |
JP2004186158A (ja) | 2004-07-02 |
US6869698B2 (en) | 2005-03-22 |
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