CN110078755B - 化合物、显示面板以及显示装置 - Google Patents
化合物、显示面板以及显示装置 Download PDFInfo
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- CN110078755B CN110078755B CN201910460184.2A CN201910460184A CN110078755B CN 110078755 B CN110078755 B CN 110078755B CN 201910460184 A CN201910460184 A CN 201910460184A CN 110078755 B CN110078755 B CN 110078755B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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Abstract
Description
技术领域
本发明涉及有机电致发光材料技术领域,具体地涉及一种化合物以及包括该化合物的显示面板以及显示装置。
背景技术
有机电致发光器件(OLEDs)根据发光激子的类别可以分为荧光器件和磷光器件。
与仅能利用单线态激子能量(25%)发光的传统荧光器件相比,磷光器件因理论上可以达到100%的内量子效率而具备更为广阔的应用前景。但磷光器件也因为含有重金属导致成本过高(几乎是荧光材料的成本的数倍),稳定性差(使用寿命短)而饱受诟病。
最近两年来,一种全新的发光材料——热致延迟荧光(Thermally ActivatedDelayed Fluorescence,TADF)材料,利用E型上转换(E-type up conversion)的原理,能同时利用单线态与三线态激子的能量,拥有更高的内量子效率;由于其与传统荧光材料一样不含重金属,可以大大降低成本并提高稳定性而备受瞩目。目前,基于此类材料的器件外量子效率(EQE)已经足可与磷光器件相匹敌。
延迟荧光为了利用三线态向单线态能级逆向窜越(RISC)从而辐射发光,必须将单线态与三线态能级差降低到可以满足逆向窜越的值(一般情况下,△EST≤0.2ev)。由于△EST与HOMO,LUMO的重叠程度满足以下关系:
即△EST与HOMO,LUMO的重叠程度正相关,如要降低△EST,需要将HOMO、LUMO尽可能地分离。
目前,制约稳定高效蓝光发光材发展的因素主要有以下几点:
(1)发射蓝光需要3.0eV的带宽,这限制了芳香化合物的共轭长度,使得分子不能有很大的共轭结构,导致发光材料分子尺寸不能过大,然而小的分子结构又会导致发光材料的热稳定性能不高;
(2)大的分子刚性结构是获得高效蓝光的必备条件,然而分子结构刚性太大会导致得到相稳定的薄膜材料困难;
(3)宽的能带使得电子和空穴的同时注入变得异常困难,打破了电子和空穴的平衡,导致发光效率下降。
引入三苯胺结构,使得化合物形成了类似于螺旋桨结构的扭曲结构,很好地避免了分子间团聚的发生,光致发光波长在436nm的深蓝光范围。由于三苯胺结构是给电子基团,可以降低器件的开启电压,该类化合物制作的OLED器件需要较低的开启电压(3.7eV),最大亮度达到13306.5cd/m2,量子效率为0.816%,发光效率为2.156cd/A-1,流明效率为1.4641m/W-1。
以下式(1)的这种螺旋桨结构的化合物虽然能很好地避免因团聚引起的量子猝灭,但是,由于其具有很大的自由体积,这将会导致其玻璃化转变温度下降,进而导致热稳定性不能满足要求。
发明内容
针对现有技术中存在的问题,根据本发明的第一方面,提供了一种化合物,所述化合物具有式(I)所示的结构:
其中,L表示取代或未取代的苯基、萘基、吡啶基、嘧啶基、吡嗪基;
D为供电子基团,各自独立地选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的苊烯基、取代或未取代的芘基、取代或未取代的苝基、取代或未取代的芴基、取代或未取代的螺双芴基、取代或未取代的基、取代或未取代的苯并菲基、取代或未取代的苯并蒽基、取代或未取代的荧蒽基、取代或未取代的苉基、取代或未取代的呋喃基、取代或未取代的苯并呋喃基、取代或未取代的二苯并呋喃基、取代或未取代的噻吩基、取代或未取代的苯并噻吩基、取代或未取代的二苯并噻吩基、取代或未取代的吩噁嗪基、取代或未取代的吩嗪基、取代或未取代的吩噻嗪基、取代或未取代的噻蒽基、取代或未取代的咔唑基、取代或未取代的吖啶基、取代或未取代的二芳胺基中的任意一种。
在本发明中,硼杂咔唑并邻菲罗啉的OLED材料用例如螺二芴等作为分子的P型生色团(电子给体单元),通过硼杂咔唑SP3杂化的连接基连接受体单元。该设计通过接入邻菲罗啉基团,能够提高材料的稳定性,有利于延长器件寿命,更能通过缩短共轭长度,提高能级,削弱分子内电荷转移,窄化发光光谱。
本发明设计的化合物具有TADF特性,可以利用传统荧光分子跃迁禁阻得三线态激子来发光,从而提高器件效率。其根本原因在于所设计分子具有大的刚性扭曲,降低了HOMO和LUMO之间的重叠,使得三重态和单重态之间的能级差可以降低到0.1eV左右,满足三线态能量向单线态逆向窜越从而提高发光效率。
根据本发明的第二方面,提供了一种显示面板,包括阳极、阴极、以及位于阳极和阴极之间的发光层,其中发光层的发光材料包括上述的化合物中的一种或一种以上。
根据本发明的第三方面,提供了显示装置,包括上述显示面板。
附图说明
图1是本发明的硼杂咔唑化合物的化学通式;
图2示出本发明的硼杂咔唑化合物M1的HOMO分布图;
图3示出本发明的硼杂咔唑化合物M1的LUMO分布图;
图4是本发明提供的OLED器件的结构示意图;
图5是本发明实施例提供的一种显示装置的示意图。
具体实施方式
下面通过实施例和对比例进一步说明本发明,这些实施例只是用于说明本发明,本发明不限于以下实施例。凡是对本发明技术方案进行修改或者等同替换,而不脱离本发明技术方案的范围,均应涵盖在本发明的保护范围中。
本发明的一方面是提供一种硼杂咔唑化合物,所述硼杂咔唑化合物具
有如图1所示的式(I)所示的结构:
其中,L表示取代或未取代的苯基、萘基、吡啶基、嘧啶基、吡嗪基;
D为供电子基团,各自独立地选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的苊烯基、取代或未取代的芘基、取代或未取代的苝基、取代或未取代的芴基、取代或未取代的螺双芴基、取代或未取代的基、取代或未取代的苯并菲基、取代或未取代的苯并蒽基、取代或未取代的荧蒽基、取代或未取代的苉基、取代或未取代的呋喃基、取代或未取代的苯并呋喃基、取代或未取代的二苯并呋喃基、取代或未取代的噻吩基、取代或未取代的苯并噻吩基、取代或未取代的二苯并噻吩基、取代或未取代的吩噁嗪基、取代或未取代的吩嗪基、取代或未取代的吩噻嗪基、取代或未取代的噻蒽基、取代或未取代的咔唑基、取代或未取代的吖啶基、取代或未取代的二芳胺基中的任意一种。
本发明中,硼杂咔唑并邻菲罗啉的OLED材料用例如螺二芴等作为分子的P型生色团(电子给体单元),通过硼杂咔唑SP3杂化的连接基连接受体单元。该设计通过接入邻菲罗啉基团,能够提高材料的稳定性,有利于延长器件寿命,更能通过缩短共轭长度,提高能级,削弱分子内电荷转移,窄化发光光谱。
本发明设计的化合物具有TADF特性,可以利用传统荧光分子跃迁禁阻得三线态激子来发光,从而提高器件效率。其根本原因在于所设计分子具有大的刚性扭曲,降低了HOMO和LUMO之间的重叠,使得三重态和单重态之间的能级差可以降低到0.1eV,满足三线态能量向单线态逆向窜越从而提高发光效率。
根据本发明所述化合物的一个实施方式,D选自以下基团中的任意一种:
Z选自C原子、N原子、O原子或S原子;q选自0、1或2;
U1、U2和U3各自独立地选自氢原子、C1-C6烷基、C1-C6烷氧基;
当Z为氧原子或硫原子时,q为0;
#表示连接位置。
在该实施方式中,本发明的化合物所含的咔唑类取代基是一种含氮芳杂环,具有特殊的刚性稠环。其具有如下特点:咔唑环易于形成相对稳定的正离子,分子内具有较大的共轭体系及强的分子内电子转移,普遍具有较高的热稳定性和光化学稳定性,咔唑环上易于进行结构修饰,引入多种官能团。咔唑自身是煤焦油产品之一,原料易得。另外,以上碳原子总数小于或等于30的咔唑类取代基与母核构成的化合物的共轭长度适中,并且在短波长的范围内有很强的吸收,其能级带隙为3.2eV左右,适用于高效的蓝光发光材料。
根据本发明所述化合物的一个实施方式,D选自以下基团中的任意一种:
根据本发明所述化合物的一个实施方式,D选自以下基团中的任意一种:
Z选自C原子、N原子、O原子、S原子或Si原子;X选自C原子、N原子、O原子或S原子;m、n、p和q各自独立地选自0、1或2;
U1、U2、U3、U4各自独立地选自氢原子、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C6-C12芳基;
当Z为氧原子或硫原子时,p为0;当X为氧原子或硫原子时,q为0;
#表示连接位置。在该实施方式中,本发明的含吖啶类取代基的化合物在外加电场的作用下可以形成铵离子自由基,三级胺上的N原子具有很强的给电子能力,因此很容易被氧化成阳离子自由基(空穴),因此其相应的空穴传输性能较好。
根据本发明所述化合物的一个实施方式,D选自以下基团中的任意一种:
其中,R和R’各自独立地选自氢原子、C1-C3烷基、苯基。在该实施方式中,本发明的化合物中所采用的吩噁嗪类取代基具有以下有益效果:氮原子上的供电子基以及氧上的孤对电子与共轭体系的相互作用,使分子的激发态更容易发生电荷转移,因此产生更好的光电转换性能。另外,以上碳原子总数小于或等于30的吩噁嗪类取代基与母核构成的化合物的共轭长度适中,适用于高效的蓝光发光材料。
根据本发明所述化合物的一个实施方式,D选自以下基团中的任意一种或一种以上:
R1、R2各自独立地选自氢原子、C1-C6烷基、C1-C6烷氧基;u、v各自独立地选自0、1或2;
#表示连接位置。本发明的含苯胺基的化合物在外加电场的作用下可以形成铵离子自由基,三级胺上的N原子具有很强的给电子能力,因此很容易被氧化成阳离子自由基(空穴),因此其相应的空穴传输性能较好。另外,以上碳原子总数小于或等于30的苯二胺类取代基与母核构成的化合物的共轭长度适中,适用于高效的蓝光发光材料。
根据本发明所述化合物的一个实施方式,D选自以下基团中的任意一种或一种以上:
其中,#表示连接位置。
根据本发明所述化合物的一个实施方式,D选自以下基团中的任意一种:
其中,X1、X2和X3各自独立地选自氢原子、C1-C6烷基、C1-C6烷氧基、C6-C12芳基、寡聚噻吩基,#表示连接位置。在该实施方式中,本发明的化合物中采用了螺二芴取代基,具有较大的共轭体系和特有的螺共轭效应,具有较好的刚性共性面,玻璃化温度高,热稳定性好。其中对于螺碳化合物,通过sp3杂化的碳原子相连的两条共轭链所形成的刚性结构能够有效地阻止激发子的形成,能够有效抑制强分子间作用以及发光过程中的非辐射跃迁,从而能有效地提高光学器件的光纯度和光稳定性。此外,当供电子基团D采用螺二芴取代基时,分子结构的刚性适中,非常适合用作高效的蓝光发光材料。
优选地,根据以上采用螺二芴取代基的化合物的一个实施方式,X1、X2和X3均为寡聚噻吩基。采用寡聚噻吩基,使得该类化台物的立体结构更为复杂,分子的共平面性明显变差从而导致分子间的不易相互排列,有效地阻止分子间的堆积,不仅使得化合物的无定型性增加,而且玻璃化转变温度也有明显的提高,从而提高器件的应用性能。
根据本发明所述化合物的一个实施方式,L选自以下基团:
D选自以下基团:
其中,U1和U2各自独立地选自C1-C3烷基;m和n各自独立地选自0、1或2,#表示连接位置。
根据本发明所述化合物的一个实施方式,L1与L2选自以下基团:
D选自以下基团:
其中,Z选自C原子、N原子、O原子或S原子;m和n为0,p为0、1或2;
U1、U2和U3各自独立地选自C1-C3烷基、C6-C12芳基;
当Z为氧原子或硫原子时,p为0;
#表示连接位置。在本发明的化合物中,当L为苯基时,可以使HOMO与LUMO更加容易分离。并且在实际制备中可以降低本发明化合物的工艺制备难度。另外,苯基为L时,对位连接的方式能够有效地调节化合物的光谱并提高热稳定性。
根据本发明所述化合物的一个实施方式,L1与L2选自以下基团:
D选自以下基团:
R1与R2各自独立地选自C1-C3烷基;u、v各自独立地选自0、1或2。
根据本发明所述化合物的一个实施方式,所述化合物选自以下化合物:
根据本发明所述化合物的一个实施方式,当所述化合物用作蓝光发光材料时,所述供电子基团D为碳原子数量不超过30的刚性分子结构。当本发明的供电子基团D为碳原子数量不超过30的刚性分子结构时,共轭长度适中,热稳定性好,非常适用于蓝光发光材料。
根据本发明所述化合物的一个实施方式,所述化合物的最低单重态能级S1与最低三重态能级T1之间的能级差ΔEst=ES1-ET1≤0.2eV。
本发明的硼杂咔唑化合物具备TADF特性,可以用作OLED发光层的主体材料或客体材料。
本发明的另一方面提供了一种显示面板,包括阳极、阴极、以及位于阳极和阴极之间的发光层,其中发光层的发光材料包括如上所述的化合物中的一种或一种以上。
根据本发明的显示面板的一个实施方式,所述发光层的发光材料包括主体材料和客体材料,所述主体材料为如上所述的化合物中的一种或一种以上。
根据本发明的显示面板的一个实施方式,包括如上所述的显示面板。本发明的示例性硼杂咔唑化合物M1、M2、M3、M4的制备方法,如下示例性实施例1至实施例4所述。
实施例1
化合物M1的合成
化合物M1的合成路线如下。
化合物M1的具体合成步骤如下。
将氨基苯并邻菲罗啉24.5g(0.1mol)溶于100ml二氯甲烷中,在氮气氛围下,缓慢滴加100ml溶有18.7g(0.1mol)NBS的二氯甲烷溶液,在室温下搅拌4h。停止反应后向反应液中5ml的水淬灭未反应的NBS,使用(50ml*3)的二氯甲烷淬取有机相,有机相旋转蒸发干溶剂后,使用100ml正己烷回流打浆过夜,冷却至室温后抽滤,得到30.7g的B(99.5%,95mmol,收率95%)。
1H NMR(500MHz,氯仿)δ8.80(s,2H),8.14(s,2H),7.46(s,1H),7.58–7.19(m,3H),4.48(s,2H)。
13C NMR(125MHz,常见的NMR溶剂)δ150.32(s),148.79(s),144.83(s),142.19(s),141.69(s),133.47(s),129.82(s),128.72(s),128.00(s),124.79(s),124.39(s),122.28(s),119.85(s),118.80(s),114.60(s),108.20(s)。
向250ml四口烧瓶中加入180ml水、20ml乙醇、30.78g(95mmol)B、19.95g(99.75mmol)邻溴苯硼酸、39.33g(285mmol)碳酸钾、38mg四三苯基膦钯、6.08g四丁基溴化铵,加热至90℃。6h后监测到反应终点,将其冷却至25℃,用MTBE(3×100mL)萃取。用水洗涤有机层并用MgSO4干燥并减压浓缩。然后通过硅胶快速柱色谱(己烷)纯化粗产物,得到黄色油状物的C(35g,87.4mmol,92%)。
1H NMR(500MHz,氯仿)δ8.80(s,2H),8.14(s,2H),7.84(s,1H),7.66(s,1H),7.54(s,1H),7.44(s,1H),7.39(s,2H),7.28(d,J=15.0Hz,2H),2.92(s,2H)。
13C NMR(125MHz,常见的NMR溶剂)δ150.32(s),148.79(s),144.83(s),143.50(s),141.69(s),139.70(s),134.17(s),133.72(s),133.47(s),132.50(s),130.87(s),130.16(s),128.72(s),128.34(s),126.95(s),124.79(s),124.39(s),122.45(s),119.85(s),118.80(s),116.12(s),111.52(s)。
向100ml 0℃的CCl4中加入35g(70mmol)的C、18.38g(262.5mmol)NaNO2、40.16g(262.5mol)TMS-Br、3.99g(17.5mmol)TEBAC的混合物,保温搅拌1.5h后自然升温,随着温度在2小时内变为环境温度,混合物由黏稠状变得透明,8小时后,对上清液的分析表明,C几乎定量地转化为D,加入20ml水进行淬灭反应,将反应液过滤,清液用100ml水洗涤分液,有机相脱溶浓缩后使用硅胶柱分离,得到化合物D(29.2g,98%,62.9mmol,收率88%)。
1H NMR(500MHz,氯仿)δ8.80(s,2H),8.15(d,J=1.4Hz,1H),8.10(d,J=45.0Hz,2H),7.84(s,1H),7.66(s,1H),7.44(s,1H),7.39(s,2H),7.29(s,1H),7.23(s,1H)。
13C NMR(125MHz,常见的NMR溶剂)δ150.32(s),149.95(s),144.83(s),144.64(s),143.68(s),141.01(s),135.08(s),134.63(s),134.03(s),130.97(s),130.32(s),129.61(s),128.72(s),127.18(s),124.39(s),123.32(s),122.19(s),122.01(s),120.26(s),120.09(s),119.85(s),118.13(s)。
在室温下,向溶有29.2g(62.9mmol)D的甲苯(500ml)溶液中缓慢滴加2.5M n-BuLi的己烷溶液(50.3ml,125.8mmol),回流5h,将反应液降温至0℃,加入1M的BCl3的庚烷溶液(62.9ml,62.9mmol),反应液逐渐变黄,在室温下搅拌15h,监控反应终点,加入100ml水淬灭未反应的n-BuLi,将反应液过滤、分液,有机相脱溶浓缩后硅胶柱分离,得到E(13.2g,37.74mmol,收率60%)。
1H NMR(500MHz,氯仿)δ8.80(s,2H),8.12(d,J=25.0Hz,3H),7.94(s,1H),7.77(s,1H),7.45(dd,J=42.5,12.5Hz,5H)。
13C NMR(125MHz,常见的NMR溶剂)δ162.46(s),161.33(s),150.32(s),149.81(s),144.83(s),144.18(s),143.14(s),141.19(s),132.07(s),130.07(d,J=6.9Hz),130.04(s),128.94(s),128.72(s),127.63(s),127.43(s),127.25(s),126.36(s),124.39(s),123.66(s),122.47(s),120.18(s),119.85(s)。
将化合物F(11.35g,28.7mmol)、化合物E(13.2g,37.74mmol)、Pd(PPh3)4(1g,0.87mmol)、K2CO3(12.05g,86.86mmol)、蒸馏水(23ml)、甲苯(113.64ml)、乙醇(23ml)混合并回流下搅拌8h,将混合物冷却至室温,加入蒸馏水,用EA萃取并用硫酸镁干燥,浓缩后硅胶柱分离,得到化合物M1(13.27g,18.8mmol,收率56%)。
1H NMR(500MHz,氯仿)δ8.80(dd,J=7.5,1.4Hz,2H),8.14(dd,J=7.5,1.4Hz,2H),8.09(d,J=7.5Hz,1H),7.95(d,J=1.6Hz,1H),7.93(d,J=1.4Hz,1H),7.92–7.87(m,3H),7.83(s,1H),7.81(s,1H),7.80(d,J=1.6Hz,1H),7.79–7.76(m,3H),7.75–7.71(m,3H),7.62(td,J=7.5,1.4Hz,1H),7.53–7.46(m,3H),7.44–7.35(m,4H),7.27–7.20(m,4H)。
13C NMR(125MHz,常见的NMR溶剂)δ150.32(s),149.81(s),147.58(s),147.28(s),146.01(s),145.52(s),144.83(s),143.14(s),141.93(s),139.30(s),138.82(s),137.02(s),134.09(s),133.74(s),130.49(s),130.07(d,J=6.8Hz),129.08(s),128.72(s),127.55(d,J=0.6Hz),126.88(s),126.78–126.60(m),126.14(s),125.28(d,J=7.4Hz),124.39(s),123.80(s),123.62(s),122.47(s),121.91(s),121.60(d,J=3.7Hz),120.18(s),119.86(d,J=1.7Hz),115.94(s),109.74(s),61.28(s)。
实施例2
化合物M2的合成
将化合物F2(9.24g,28.7mmol)、化合物E(13.2g,37.74mmol)、Pd(PPh3)4(1g,0.87mmol)、K2CO3(12.05g,86.86mmol)、蒸馏水(23ml)、甲苯(113.64ml)、乙醇(23ml)混合并回流下搅拌8h,将混合物冷却至室温,加入蒸馏水,用EA萃取并用硫酸镁干燥,浓缩后硅胶柱分离,得到化合物M2(10.5g,18.8mmol,收率56%)。
1H NMR(500MHz,氯仿)δ8.80(dd,J=7.5,1.4Hz,2H),8.14(dd,J=7.5,1.4Hz,2H),8.09(d,J=7.5Hz,1H),7.95(d,J=1.6Hz,1H),7.93(d,J=1.4Hz,1H),7.92–7.87(m,3H),7.83(s,1H),7.81(s,1H),7.80(d,J=1.6Hz,1H),7.79–7.76(m,3H),7.75–7.71(m,3H),7.62(td,J=7.5,1.4Hz,1H),7.53–7.46(m,3H),7.44–7.35(m,4H),7.27–7.20(m,4H)。
13C NMR(125MHz,常见的NMR溶剂)δ150.32(s),149.81(s),147.58(s),147.28(s),146.01(s),145.52(s),144.83(s),143.14(s),141.93(s),139.30(s),138.82(s),137.02(s),134.09(s),133.74(s),130.49(s),130.07(d,J=6.8Hz),129.08(s),128.72(s),127.55(d,J=0.6Hz),126.88(s),126.78–126.60(m),126.14(s),125.28(d,J=7.4Hz),124.39(s),123.80(s),123.62(s),122.47(s),121.91(s),121.60(d,J=3.7Hz),120.18(s),119.86(d,J=1.7Hz),115.94(s),109.74(s),61.28(s)。
实施例3
化合物M3的合成
将化合物F3(9.7g,28.7mmol)、化合物E(13.2g,37.74mmol)、Pd(PPh3)4(1g,0.87mmol)、K2CO3(12.05g,86.86mmol)、蒸馏水(23ml)、甲苯(113.64ml)、乙醇(23ml)混合并回流下搅拌8h,将混合物冷却至室温,加入蒸馏水,用EA萃取并用硫酸镁干燥,浓缩后硅胶柱分离,得到化合物M3(10.78g,18.8mmol,收率56%)。
1H NMR(500MHz,氯仿)δ8.80(dd,J=7.5,1.4Hz,2H),8.14(dd,J=7.5,1.4Hz,2H),8.09(d,J=7.5Hz,1H),7.95(d,J=1.6Hz,1H),7.93(d,J=1.4Hz,1H),7.92–7.87(m,3H),7.83(s,1H),7.81(s,1H),7.80(d,J=1.6Hz,1H),7.79–7.76(m,3H),7.75–7.71(m,3H),7.62(td,J=7.5,1.4Hz,1H),7.53–7.46(m,3H),7.44–7.35(m,4H),7.27–7.20(m,4H)。
13C NMR(125MHz,常见的NMR溶剂)δ150.32(s),149.81(s),147.58(s),147.28(s),146.01(s),145.52(s),144.83(s),143.14(s),141.93(s),139.30(s),138.82(s),137.02(s),134.09(s),133.74(s),130.49(s),130.07(d,J=6.8Hz),129.08(s),128.72(s),127.55(d,J=0.6Hz),126.88(s),126.78–126.60(m),126.14(s),125.28(d,J=7.4Hz),124.39(s),123.80(s),123.62(s),122.47(s),121.91(s),121.60(d,J=3.7Hz),120.18(s),119.86(d,J=1.7Hz),115.94(s),109.74(s),61.28(s)。
实施例4
化合物M4的合成
将化合物F(10.92g,28.7mmol)、化合物E(13.2g,37.74mmol)、Pd(PPh3)4(1g,0.87mmol)、K2CO3(12.05g,86.86mmol)、蒸馏水(23ml)、甲苯(113.64ml)、乙醇(23ml)混合并回流下搅拌8h,将混合物冷却至室温,加入蒸馏水,用EA萃取并用硫酸镁干燥,浓缩后硅胶柱分离,得到化合物M4(13.46g,18.8mmol,收率56%)。
1H NMR(500MHz,氯仿)δ8.80(dd,J=7.5,1.4Hz,2H),8.14(dd,J=7.5,1.4Hz,2H),8.09(d,J=7.5Hz,1H),7.95(d,J=1.6Hz,1H),7.93(d,J=1.4Hz,1H),7.92–7.87(m,3H),7.83(s,1H),7.81(s,1H),7.80(d,J=1.6Hz,1H),7.79–7.76(m,3H),7.75–7.71(m,3H),7.62(td,J=7.5,1.4Hz,1H),7.53–7.46(m,3H),7.44–7.35(m,4H),7.27–7.20(m,4H)。
13C NMR(125MHz,常见的NMR溶剂)δ150.32(s),149.81(s),147.58(s),147.28(s),146.01(s),145.52(s),144.83(s),143.14(s),141.93(s),139.30(s),138.82(s),137.02(s),134.09(s),133.74(s),130.49(s),130.07(d,J=6.8Hz),129.08(s),128.72(s),127.55(d,J=0.6Hz),126.88(s),126.78–126.60(m),126.14(s),125.28(d,J=7.4Hz),124.39(s),123.80(s),123.62(s),122.47(s),121.91(s),121.60(d,J=3.7Hz),120.18(s),119.86(d,J=1.7Hz),115.94(s),109.74(s),61.28(s)。
实施例5
利用Gaussian软件模拟本发明所述的示例性硼杂咔唑化合物M1、M2、M3和M4的电致发光性质。
图2和图3分别示出了本发明的示例性硼杂咔唑化合物M1的HOMO和LUMO能级图。由图2和图3可以明显地看出,化合物分子M1的HOMO和LUMO分别排布在给体单元和受体单元上,降低了HOMO和LUMO的完全分离,这有助于减小系间能差△EST,从而提高逆系间窜越能力。
对硼杂咔唑化合物M1、M2、M3和M4的HOMO、LUMO以及其他参数进行了测试,得到的结果如表1所示。
表1四个代表性硼杂咔唑化合物的参数
从表1可以看出,本发明的硼杂咔唑化合物具有明显更低的LUMO能级,从而使电子跃迁更容易发生。本发明的硼杂咔唑化合物的最低单重态能级S1与最低三重态能级T1之间的能级差ΔEst=ES1-ET1≤0.2eV,实现了较小的单线态和三线态能级差,适于作为热活化延迟荧光材料。(表1中,S1表示单线态能级,T1表示三线态能级,△EST表示单线态和三线态能级差,τ表示激子寿命)。
本发明的另一方面提供了一种显示面板,所述显示面板包括有机发光器件,所述有机发光器件包括阳极、阴极、以及位于阳极和阴极之间的发光层,其中发光层的发光材料包括本发明所述的硼杂咔唑化合物中的一种或多种。
根据本发明所述显示面板的一个实施方式,所述发光层的发光材料包括主体材料和客体材料,其中所述主体材料为本发明所述化合物中的一种或多种。
根据本发明所述显示面板的一个实施方式,所述有机发光器件还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层或电子注入层中的一层或多层。
在本发明所述显示面板的一个实施方式中,有机发光器件(OLED)的结构如图4所示。其中,1为玻璃或其他适合材质(如塑料)做成的基底(substrate);2为ITO或IGZO等透明阳极;3为有机膜层(包括发光层);4为金属阴极,共同构成一个完整的OLED器件。两个电极1和4可以互换。
在本发明提供的显示面板中,有机发光器件的阳极材料可以选自金属例如铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金。阳极材料也可以选自金属氧化物如氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)等;阳极材料还可以选自导电性聚合物例如聚苯胺、聚吡咯、聚(3-甲基噻吩)等。此外,阳极材料还可以选自除以列举的阳极材料以外的有助于空穴注入的材料及其组合,其包括已知的适合做阳极的材料。
在本发明提供的显示面板中,有机发光器件的阴极材料可以选自金属例如铝、镁、银、铟、锡、钛等及它们的合金。阴极材料也可以选自多层金属材料例如LiF/Al、LiO2/Al、BaF2/Al等。除了以上列举的阴极材料以外,阴极材料还可以是有助于电子注入的材料及其组合,包括已知的适合做阴极的材料。
在本发明的显示面板中,有机发光器件可以这样制作:在透明或不透明的光滑的基板上形成阳极,在阳极上形成有机薄层,在有机薄层上形成阴极。有机薄层的形成可以采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
下面的实施例6和实施例7提供了示例性的实施例,用于说明本发明的硼杂咔唑化合物在有机发明显示面板中的实际应用。
实施例6
有机发光器件制作步骤:
将具有膜厚为100nm的ITO薄膜的阳极基板用蒸馏水、丙酮、异内醇超声清洗并放入烘箱干燥,通过UV处理表面30分钟,然后移至真空蒸镀腔中。在真空度为2×10-6Pa下开始蒸镀各层薄膜,蒸镀5nm厚的HATCN形成空穴注入层,蒸镀40nm厚的N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPD),然后蒸镀10nm厚的4,4',4”-三(咔唑-9-基)三苯胺(TCTA)形成空穴传输层(HTL)。在空穴传输层上,用本发明的目标化合物作为发光层的掺杂材料,3,3'-二(N-咔唑基)-1,1'-联苯(mCBP)作为发光层的主体材料,同时蒸镀该掺杂材料和主体材料,形成35nm厚的发光层。然后在发光层上蒸镀二苯基[4-(三苯基硅烷基)苯基]氧膦(TSPO1)形成5nm厚的空穴阻挡层(HBL)。在空穴阻挡层上蒸镀4,7-二苯基-1,10-菲啰啉(Bphen)以形成30nm的电子传输层(ETL)。在电子传输层上依次蒸镀2.5nm厚的LIF和100nm厚的Al作为电子注入层(EIL)和阴极,从而制成有机发光显示装置。
以本发明的硼杂环化合物M1例,将M1其作为荧光掺杂剂,设计以下发光器件D1。发光器件D1的结构如下:
ITO(100nm)/HATCN(5nm)/α-NPD(40nm)/TCTA(10nm)/CBP:M1(35n m,8%)/TSPO1(5nm)/Bphen(30nm)/LiF(2.5nm)/Al(100nm)。
在上述发光器件的结构的基础上,将上述发光器件中的荧光掺杂剂硼杂环化合物M1替换为本发明的硼杂环化合物M2、M3和M4,设计发光器件D2、D3、D4。
作为对比,在上述发光器件的结构的基础上,将上述发光器件中的荧光掺杂剂硼杂环化合物M1替换为DCJTB,设计对比器件Dref。
实施例7
以本发明的硼杂咔唑化合物M1、M2、M3、M4例,将其作为荧光掺杂剂,分别设计以下发光器件D1、D2、D3和D4。
表2器件发光性能测定结果
Vturn-on:启电压;EL(10mA/cm 2 ):电流密度为10mA/cm2时的电流效率;PE(max):最大功率效率;EQE(max):外量子效率(External Quantum Efficiency);CIE(x,y):色坐标
采用本发明化合物的OLED器件具有较高的外量子效率(EQE),最大能达到6.97%。与对比例Dref相比较,本发明的硼杂咔唑化合物的结构具有TADF特性,当其用在有机发光器件中时,可以利用传统荧光分子跃迁禁阻的三线态激子来发光,从而提高器件效率。同时,含有咔唑基团的化合物TADF材料本身具有双极性特性,其作为发光层的材料可以大大提高两种载流子的传输能力和改善载流子平衡,提高荧光外量子效率,最大能达到6.97%。
本发明的又一方面还提供一种显示装置,其包括如上文所述的有机发光显示面板。
在本发明中,有机发光器件可以是OLED,其可以用在有机发光显示装置中,其中有机发光显示装置可以是手机显示屏、电脑显示屏、液晶电视显示屏、智能手表显示屏、智能汽车显示面板、VR或AR头盔显示屏、各种智能设备的显示屏等。图5是根据本发明实施例提供的一种显示装置的示意图。在图5中,10表示手机显示面板,20表示显示装置。
本申请虽然以较佳实施例公开如上,但并不是用来限定权利要求,任何本领域技术人员在不脱离本申请构思的前提下,都可以做出若干可能的变动和修改,因此本申请的保护范围应当以本申请权利要求所界定的范围为准。
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