CN111253393B - 长寿命三线态激子限域材料及其在oled器件中的应用 - Google Patents
长寿命三线态激子限域材料及其在oled器件中的应用 Download PDFInfo
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Abstract
本发明涉及有机发光技术领域,尤其涉及一种长寿命三线态激子限域材料及其在OLED器件中的应用。所述激子限域材料具有式(I)、式(II)、式(Ⅲ)或式(IV)所示结构:D‑A(I);D‑π‑A(II);A‑D‑A(III);A‑π‑D‑A(IV);D选自芘基、三亚苯基、
Description
技术领域
本发明涉及有机发光技术领域,尤其涉及一种长寿命三线态激子限域材料及其在OLED器件中的应用。
背景技术
自从高效率的电致发光在有机小分子和共轭聚合物薄膜中被发现以来,大量的研究人员投入到这一领域。目前为止,有机发光二极管已成为平面显示技术(如智能手机显示,电视等)的首选,特别是柔性显示。有机发光二极管的出现,不仅使得色彩艳丽的平面显示成为可能,同时也展现出了成为下一代节能照明技术的巨大潜力。由于磷光材料及热活化延迟荧光材料的引入,使得器件可以达到100%的内部量子效率,尽管如此,器件仍然面临着效率滚降和器件使用寿命不足的严峻挑战。
比如通常激子限域材料的开发需要满足i)高电子迁移率来改善器件电荷传输平衡,提高器件效率;ii)高三重态能级改善器件的激子限域能力,提高器件效率;iii)高的化学及热稳定性提高器件的寿命。但是目前的激子限域材料很难同时满足以上三个条件,特别是对于蓝、绿光更是如此。因为随着发光波长越短,需要传输材料的三重态能级更高,才能有效限域高能量激子的逃逸,相应的能隙越宽,而随着能隙的变宽,其传输能力及稳定性往往下降,所以高迁移率及稳定性与高三重态很难同时实现。
发明内容
有鉴于此,本发明要解决的技术问题在于提供一种长寿命三线态激子限域材料及其在OLED器件中的应用,本发明提供的长寿命三线态激子限域材料可以限域高能量激子,电子传输性能较优,作为OLED器件的发光层主体材料和/或电子传输层材料时,可以获得较高的器件效率,且寿命较长。
本发明提供了一种长寿命三线态激子限域材料,具有式(I)、式(II)、式(Ⅲ)或式(IV)所示结构:
A选自吡嗪并邻菲罗啉基、苯并邻菲罗啉基、邻菲罗啉基、吖啶基、吩嗪基、二苯并-γ-吡喃酮基、1,8-萘啶基或1,5-萘啶基;
π选自含有取代基团的苯基或二苯并六元杂环基。
优选的,所述π选自式(1)~式(6)所示结构中的一种:
R1、R2和R3独立地选自碳原子数为1~6的烷基。
优选的,R1、R2和R3独立地选自甲基、乙基或叔丁基。
优选的,所述D为端基时,选自式(7)~式(12)所示结构中的一种:
优选的,所述D为端基时,选自式(7-1)~式(12-1)所示结构中的一种:
优选的,所述D为中间基团时,选自式(13)~式(78)所示结构中的一种:
优选的,所述A选自式(79)~式(86)所示结构中的一种:
优选的,所述A选自式(79-1)~式(85-1)所示结构中的一种:
优选的,所述长寿命三线态激子限域材料选自式(87)~(131)中的一种:
优选的,所述长寿命三线态激子限域材料的三线态寿命为1ms~10s。
本发明还提供了一种上文所述的长寿命三线态激子限域材料运用于有机发光器件中,作为发光层主体材料和/或电子传输层材料的应用。本来低三线态能量的材料不能限域高能量激子,而本发明提供的长寿命三线态激子限域材料为ms级,寿命长,可以限域高能量激子,电子传输性能较优,作为发光层主体材料和/或电子传输层材料时,可以获得较高的器件效率。因而,本发明请求保护上文所述的长寿命三线态激子限域材料运用于有机发光器件中,作为发光层主体材料和/或电子传输层材料的应用。
优选的,所述有机发光器件的结构包括第一电极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/第二电极。
在本发明的某些实施例中,所述第一电极为ITO透明电极。在本发明的某些实施例中,所述第二电极为Al。在本发明的某些实施例中,所述空穴注入层的材料为HAT-CN。在本发明的某些实施例中,所述空穴传输层的材料为NPB。在本发明的某些实施例中,所述电子阻挡层的材料为TCTA。在本发明的某些实施例中,所述发光层的材料包括发光层主体材料和Ir(ppy)3。在本发明的某些实施例中,所述发光层主体材料为DIC-TRZ或上文所述的长寿命三线态激子限域材料。在本发明的某些实施例中,所述电子传输层材料为TPBi或上文所述的长寿命三线态激子限域材料。在本发明的某些实施例中,所述电子注入层的材料为LiF。
本发明提供的长寿命三线态激子限域材料寿命长(ms及以上),可以限域高能量激子,电子传输性能较优,作为发光层主体材料和/或电子传输层材料时,可以获得较高的器件效率和稳定性。
具体实施方式
下面将结合本发明实施例,对本发明的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。本发明对所述原料的来源并无特殊的限制,可以为一般市售。
实施例1
式(130)所述长寿命三线态激子限域材料M1的合成:
1)于2L三口瓶中搅拌加入650mL 1,4-二氧六环、0.174mol 1-溴-4-碘二苯并[b,e][1,4]二恶英、0.166mol 4-芘硼酸、72g碳酸钾和100mL水,N2保护下加入1.4g四三苯基膦钯,保持N2环境下升温至溶液温度85℃,溶液为黑色,保持85℃反应12h,原料反应完毕降温至室温,过滤后,干燥,得到产品0.1mol,纯度为99.4%。
2)于1L三口瓶中搅拌加入450mL 1,4-二氧六环、0.1mol第一步产品、0.1308mol联硼酸频哪醇酯、25g乙酸钾和1g 132钯,在N2保护下升温至回流温度85℃,溶液未全溶为黄色。回流后溶液变灰棕色,有气体生成,反应3h原料消失,停止反应,降温至室温,过滤后,干燥,得到产品0.065mol。
3)于1L三口瓶中搅拌加入320mL 1,4-二氧六环、0.065mol第二步产品、0.065mol3-溴邻菲罗啉、23g碳酸钾和1g二茂铁二氯化钯,N2保护下升温至回流温度85℃,溶液未全溶为黄色。回流时有引发现象,有气体生成,反应液开始溶解。反应12h后原料剩余0.7wt%,14h后反应结束,降温至室温,过滤后,干燥,得到激子限域材料(纯度99.9%,0.045mol)。
对得到的材料进行元素分析,得到其中各原子的含量,结果如下:
化学式:C40H22N2O2;
m/z:562.17。
元素分析:C,85.39;H,3.94;N,4.98;O,5.69
1H-NMR(300MHz,CDCl3)(ppm)δ=6.82(2H,t),6.94(2H,t),7.56(1H,m),7.64(2H,s),7.91~7.92(2H,m),8.04~8.20(10H,m),8.26(1H,d),8.45(1H,m),8.80(1H,m)。
实施例2
式(131)所述长寿命三线态激子限域材料M2的合成:
于1L三口瓶中搅拌加入500mL 1,4-二氧六环,0.1mol 1-溴吩嗪,0.11mol克莱森-5-硼酸,24.3g碳酸钾,0.43g二茂铁二氯化钯,N2保护下升温至回流,溶液未全溶为黄色。后处理得到淡黄色产品41g,纯度94.3%。
化学式:C30H18N2;
m/z:406.15。
元素分析:C,88.64;H,4.46;N,6.89
1H-NMR(300MHz,CDCl3)(ppm)δ=7.63~7.70(7H,m),7.80~7.90(7H,m),8.02(1H,t),8.22(1H,s),8.84(1H,d),8.98(1H,s)。
实施例3
式(128)所述长寿命三线态激子限域材料M3的合成:
于1L三口瓶中搅拌加入500mL 1,4-二氧六环,0.1mol 1-溴吖啶,0.11mol菲-9-基硼酸,24.3g碳酸钾,0.43g二茂铁二氯化钯,N2保护下升温至回流,溶液未全溶为黄色。后处理得到淡黄色产品32g,纯度91.5%。
化学式:C27H17N;
m/z:355.14。
元素分析:C,91.24;H,4.82;N,3.94
1H-NMR(300MHz,CDCl3)(ppm)δ=7.63~8.11(14H,m),8.79~8.84(2H,m),9.08(1H,d)。
实施例4
式(129)所述长寿命三线态激子限域材料M4的合成:
于1L三口瓶中搅拌加入500mL 1,4-二氧六环,0.1mol 4-溴占吨酮,0.11mol 2-三亚苯基硼酸,24.3g碳酸钾,0.43g二茂铁二氯化钯,N2保护下升温至回流,溶液未全溶为黄色。后处理得到淡黄色产品39g,纯度91.0%。
化学式:C31H18O2;
m/z:422.13。
元素分析:C,88.13;H,4.29;O,7.57
1H-NMR(300MHz,CDCl3)(ppm)δ=7.24(1H,m),7.36~7.42(2H,m),7.52(1H,t),7.64~7.80(7H,m),8.14(1H,d),8.30~8.37(4H,m),8.79(1H,d),9.27(1H,d)。
实施例5
长寿命三线态激子限域材料作为电子传输层材料在有机电致发光器件中的应用:
本实施例按照下述方法制备绿色电致发光器件:
a)清洗ITO玻璃:分别用去离子水、丙酮、乙醇超声清洗ITO玻璃各15min,然后在等离子体清洗器中处理2min;
g)在LiF之上真空蒸镀阴极Al,厚度为120nm。
器件结构为ITO/HAT-CN(5nm)/NPB(40nm)/TCTA(5nm)/DIC-TRZ:Ir(ppy)3(8wt%,20nm)/ETL(40nm)/LiF(0.7nm)/Al。
电子传输层(ETM)的材料分别使用了实施例1~4制得的长寿命三线态激子限域材料(M1,M2,M3,M4),并与使用TPBi作电子传输材料的器件性能进行比较,检测结果如表1所示:
表1 M1,M2,M3,M4作为电子传输材料的器件性能
通过表1中的数据可以看出,本发明的材料作为电子传输材料可以降低OLED器件的驱动电压,提高OLED器件的寿命、效率及亮度。
实施例6
长寿命三线态激子限域材料作为发光层主体材料在有机电致发光器件中的应用:
本实施例按照下述方法制备绿色电致发光器件:
a)清洗ITO玻璃:分别用去离子水、丙酮、乙醇超声清洗ITO玻璃各15min,然后在等离子体清洗器中处理2min;
g)在LiF之上真空蒸镀阴极Al,厚度为120nm。
器件结构为ITO/HAT-CN(5nm)/NPB(40nm)/TCTA(5nm)/主体:Ir(ppy)3(8wt%,20nm)/TPBi(40nm)/LiF(0.7nm)/Al。主体材料分别使用了实施例1~4制得的长寿命三线态激子限域材料(M1,M2,M3,M4),并与使用DIC-TRZ作发光层主体材料的器件性能进行比较,检测结果如表2所示:
表2 M1,M2,M3,M4作为发光层主体材料的器件性能
通过表2中的数据可以看出,本发明的材料作为发光主体可以降低OLED器件的驱动电压,提高OLED器件的寿命、效率及亮度。
实施例7
长寿命三线态激子限域材料作为发光层主体材料及电子传输材料在有机电致发光器件中的应用:
本实施例按照下述方法制备绿色电致发光器件:
a)清洗ITO玻璃:分别用去离子水、丙酮、乙醇超声清洗ITO玻璃各15min,然后在等离子体清洗器中处理2min;
g)在LiF之上真空蒸镀阴极Al,厚度为120nm。
器件结构为ITO/HAT-CN(5nm)/NPB(40nm)/TCTA(5nm)/主体:Ir(ppy)3(8wt%,20nm)/ETM(40nm)/LiF(0.7nm)/Al。
发光层主体材料及电子传输材料均分别使用了实施例1~4制得的长寿命三线态激子限域材料(M1,M2,M3,M4),并与使用TPBi作为发光层主体材料和电子传输层材料的器件性能进行比较,检测结果如表3所示:
表3 M1,M2,M3,M4作为发光层主体材料和电子传输层材料的器件性能
通过表3中的数据可以看出,本发明的材料同时作为发光主体材料及电子传输材料可以降低OLED器件的驱动电压,提高OLED器件的寿命、效率及亮度。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (7)
5.根据权利要求1所述的长寿命三线态激子限域材料,其特征在于,所述长寿命三线态激子限域材料的三线态寿命为1ms~10s。
6.权利要求1~5任意一项所述的长寿命三线态激子限域材料运用于有机发光器件中,作为发光层主体材料和/或电子传输层材料的应用。
7.根据权利要求6所述的应用,其特征在于,所述有机发光器件的结构包括第一电极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/第二电极。
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