CN111170928B - 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 PDF

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CN111170928B
CN111170928B CN202010005739.7A CN202010005739A CN111170928B CN 111170928 B CN111170928 B CN 111170928B CN 202010005739 A CN202010005739 A CN 202010005739A CN 111170928 B CN111170928 B CN 111170928B
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compound
electron
display panel
layer
light emitting
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CN111170928A (zh
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冉佺
张磊
高威
牛晶华
代文朋
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Xiamen Tianma Microelectronics Co Ltd
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Abstract

本发明提供了化学式1所示的化合物,Ar1、Ar2、Ar3和Ar4选自C6‑C40芳基、C5‑C40杂芳基;R1和R2选自‑C(R)2‑、‑N(R)‑、‑O‑、‑S‑;X1、X2和X3选自C原子或N原子;L1和L2选自亚苯基、亚萘基、亚联苯基;Y1和Y2选自含氮杂环类取代基、含氰基类取代基。本发明中X1、X2和X3所在的苯环或氮杂环两个取代位点上连接给电子基团,使化合物具有传输空穴的能力,另一个取代位点上连接含吸电子单元的氨基基团,使化合物达到传输电子的能力,通过引入双极传输主体有利于发光层中的电荷传输平衡,可以拓宽激子复合区域,简化器件结构,提高器件效率。本发明还提供显示面板和显示装置。

Description

化合物、显示面板以及显示装置
技术领域
本发明属于有机电致发光材料技术领域,具体地涉及一种可以用作OLED发光主体材料的化合物以及包含该化合物的显示面板以及显示装置。
背景技术
有机电致发光材料(OLED)作为新一代显示技术,具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点,已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
按发光机理,OLED发射的光可以分为电致荧光和电致磷光两种。荧光是单重态激子的辐射衰减跃迁所发射的光,磷光则是三重态激子辐射衰减到基态所发射的光。根据自旋量子统计理论,单重态激子和三重态激子的形成概率比例是1:3。荧光材料内量子效率不超过25%,外量子效率普遍低于5%;电致磷光材料的内量子效率理论上达到100%,外量子效率可达20%。1998年,我国吉林大学的马於光教授和美国普林斯顿大学的Forrest教授分别报道了采用锇配合物和铂配合物作为染料掺杂入发光层,第一次成功得到并解释了磷光电致发光现象,并开创性的将所制备磷光材料应用于电致发光器件。
由于磷光重金属材料有较长的寿命(μs),在高电流密度下,可能导致三线态-三线态湮灭和浓度淬灭,造成器件性能衰减,因此通常将重金属磷光材料掺杂到合适的主体材料中,形成一种主客体掺杂体系,使得能量传递最优化,发光效率和寿命最大化。在目前的研究现状中,重金属掺杂材料商业化已成熟,很难开发可替代的掺杂材料。因此,研发新的磷光主体材料成为了一个新的方向。
到目前为止,许多典型的主体材料,例如,咔唑衍生物9,9'-(1,3-苯基)-二-9H-咔唑(mCP)在OLED器件中已被广泛使用,但是其玻璃化转变温度相对较低(55℃左右),导致热稳定性和成膜性差,在器件蒸镀中不稳定。此外,由于mCP缺少吸电子基团,使其难以实现在OLED器件中空穴和电子相平衡的目的。因此,为了实现更好的OLED器件的性能,需要开发性能更加优异的OLED发光主体材料。
发明内容
有鉴于此,本发明提供一种可以用作发光主体材料的化合物,所述化合物具有化学式1所示的化学结构:
Figure BDA0002355214860000021
化学式1
其中,Ar1、Ar2、Ar3和Ar4各自独立地选自氢原子、氘原子、C1-C20烷基、C1-C20烷氧基、C1-C20烷硫基、C3-C20环烷基、取代或未取代的C6-C40芳基、取代或未取代的C5-C40杂芳基中的一种或多种,n1、n2、n3、n4各自独立地选自0、1、2;
R1和R2各自独立地选自-C(R)2-、-O-、-S-、-N(R)-、-Si(R)2-;R选自C1-C20烷基、C1-C20烷氧基、C1-C20烷硫基、C3-C20环烷基、取代或未取代的C6-C30芳基、或取代或未取代的C5-C30杂芳基;
X1、X2和X3各自立地选自C原子或N原子;
L1和L2各自独立地选自亚苯基、亚萘基、亚蒽基、亚菲基、亚芘基、亚联苯基;
Y1和Y2表示吸电子基团,且Y1和Y2各自独立地选自含氮杂环类取代基、含氰基类取代基、含羰基类取代基、含砜类取代基、含磷氧基或磷硫基类取代基、或硼杂环类取代基。
本发明的化合物中,X1、X2和X3所在的中央苯环或氮杂环的两个取代位点上连接给电子基团,使化合物具有传输空穴的能力;在另一个取代位点上连接含吸电子单元的氨基基团,使化合物达到传输电子的能力,从而使材料具有同时传输空穴和电子的能力。当本发明的化合物用作发光层主体材料时,化合物的双极性特性有利于发光层中的电荷传输平衡。通过在发光层中引入双极传输主体,可以拓宽激子复合区域,简化器件结构,提高器件效率。
此外,本发明的化合物中的两个给电子基团和一个含吸电子基单元的间位的连接方式使得分子具有较大的空间位阻,避免了分子的堆积。另外,这些基团的引入一定程度上增大了化合物的分子量,使化合物具有较高的玻璃化转变温度,在器件蒸镀中更能形成无定形的薄膜,从而达到量产的需求。
附图说明
图1是本发明实施例提供的化合物的化学通式;
图2是本发明实施例提供的一种OLED器件的结构示意图;
图3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。
本发明的一方面提供一种化合物,所述化合物具有化学式1所示的化学结构:
Figure BDA0002355214860000041
化学式1
其中,Ar1、Ar2、Ar3和Ar4各自独立地选自氢原子、氘原子、C1-C20烷基、C1-C20烷氧基、C1-C20烷硫基、C3-C20环烷基、取代或未取代的C6-C40芳基、取代或未取代的C5-C40杂芳基中的一种或多种,n1、n2、n3、n4各自独立地选自0、1、2;
R1和R2各自独立地选自-C(R)2-、-O-、-S-、-N(R)-、-Si(R)2-;R选自C1-C20烷基、C1-C20烷氧基、C1-C20烷硫基、C3-C20环烷基、取代或未取代的C6-C30芳基、或取代或未取代的C5-C30杂芳基;
X1、X2和X3各自立地选自C原子或N原子;
L1和L2各自独立地选自亚苯基、亚萘基、亚蒽基、亚菲基、亚芘基、亚联苯基;
Y1和Y2表示吸电子基团,且Y1和Y2各自独立地选自含氮杂环类取代基、含氰基类取代基、含羰基类取代基、含砜类取代基、含磷氧基或磷硫基类取代基、或硼杂环类取代基。
本发明的化合物中,X1、X2和X3所在的中央苯环或氮杂环的两个取代位点(1-位、3-位;即,X1与X3以及X2与X3之间的位点)上连接给电子基团,使化合物具有传输空穴的能力;在另一个取代位点(5位;X1与X2之间的位点)上连接含吸电子单元的氨基基团,使化合物达到传输电子的能力,从而使材料具有同时传输空穴和电子的双极性特性。当本发明的化合物用作发光层主体材料时,化合物的双极性特性有利于发光层中的电荷传输平衡。通过在发光层中引入双极传输主体,可以拓宽激子复合区域,简化器件结构,提高器件效率。
根据本发明所述化合物一种实施方式,其中,Y1和Y2选自相同的基团。
结构对称对于化合物的合成更为简单有利。这里列举的Y1和Y2选自相同的基团的情形只是其中的一些结构对称的情形,结构分子的不对称情形对于实现本发明的目的而言也是可以的。
根据本发明所述化合物一种实施方式,所述化合物具有如下所示的结构:
Figure BDA0002355214860000051
根据本发明所述化合物一种实施方式,所述化合物具有如下所示结构:
Figure BDA0002355214860000052
根据本发明所述化合物一种实施方式,所述化合物具有如下所示的结构:
Figure BDA0002355214860000061
吖啶类衍生物的给电子能力强于咔唑类衍生物的。因此,当1,3位连接相同的给电子基团时,其HOMO能级相差较大。当中心苯环的1、3位连接两个不同基团时,可以相应的改变其给电子能力,HOMO能级位于吖啶类和咔唑类衍生物之间,实现能级的调控,更能满足器件制备中匹配相邻功能层能级的要求。
根据本发明所述化合物一种实施方式,所述化合物具有以下任一种结构:
Figure BDA0002355214860000071
根据本发明所述化合物一种实施方式,所述含氮杂环类取代基选自以下基团中的任意一种:
Figure BDA0002355214860000081
其中,#表示在化学式1中的连接位置。
根据本发明所述化合物一种实施方式,所述含氰基类取代基选自以下基团中的任意一种:
Figure BDA0002355214860000082
其中,#表示在化学式1中可能的连接位置。
含氰基类取代基是也常见的电子受体。在本发明的化合物中,带氰基的苯环或氮杂环,它们的稳定性优于单纯的氰基,从而使整个双极性主体材料具有更高的稳定性。
根据本发明所述化合物一种实施方式,所述含羰基类取代基选自以下基团中的任意一种:
Figure BDA0002355214860000091
其中,#表示在化学式1中的连接位置,R表示C1-C20烷基、C1-C20烷氧基、C2-C20烯基、C2-C20炔基、C4-C8环烷基、C6-C40芳香基、C4-C40杂芳基。
根据本发明所述化合物一种实施方式,所述含砜类取代基选自以下基团中的任意一种:
Figure BDA0002355214860000092
根据本发明所述化合物一种实施方式,所述含膦氧基或膦硫基类取代基选自以下基团中的任意一种:
Figure BDA0002355214860000101
所述X选自O、S、-BR41、-C(R41)2、-Si(R41)2和-NR41中的任意一种;
所述R30、R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41各自独立地选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C2-C40杂芳基中的任意一种;
#表示在化学式1中的连接位置。
根据本发明所述化合物一种实施方式,所述硼杂环类取代基选自以下基团中的一种:
Figure BDA0002355214860000102
#表示在化学式1中的连接位置。
根据本发明所述化合物一种实施方式,X1、X2和X3中至少有一个为氮原子。
D-A型双极性主体材料的电子及空穴迁移不一定匹配,在这种D-A型双极性主体材料中,大多是空穴迁移率大于电子迁移率。在本发明的化合物中,当X1、X2和X3所在的环含有氮时,由于氮杂环具有吸电子性质,因此中心的氮杂环可以提升电子传输性能,使电子与空穴的传输具有更高的匹配度,载流子传输更加平衡。同时,氮原子取代后的化合物可能会形成分子内及分子间氢键,使得化合物更为稳定。
根据本发明所述化合物一种实施方式,R1和R2各自独立地选自-C(R)2-、-N(R)-或-Si(R)-,L1和L2各自独立地为亚苯基;其中,R的定义与权利要求1中关于R的定义相同。在这种实施方式中,通过R基团的变化,可以平衡电子传输能力和空穴传输能力。L1和L2为亚苯基时,第一方面,可以降低合成原料的成本,合成更为简单高效,更利于量产生产;第二方面,分子量适中,不会太大,蒸镀温度不会太高,材料的热稳定性得以保证,有利于蒸镀工艺生产;第三方面,对于发光主体材料而言,HOMO/LUMO要有足够的交叠以确保高效的电子交换,从而实现较高的效率,使用亚苯基能够使得此类D-A主体材料的HOMO/LUMO有所交叠,以便于电子交换。
根据本发明所述化合物一种实施方式,Ar1、Ar2、Ar3和Ar4各自独立地选自取代或未取代的C6-C40芳基或取代或未取代的C5-C40杂芳基,Y1和Y2各自独立地选自含氮杂环类取代基。
根据本发明所述化合物一种实施方式,所述化合物选自下列化合物:
Figure BDA0002355214860000121
Figure BDA0002355214860000131
Figure BDA0002355214860000141
Figure BDA0002355214860000151
Figure BDA0002355214860000161
Figure BDA0002355214860000171
Figure BDA0002355214860000181
Figure BDA0002355214860000191
Figure BDA0002355214860000201
本发明还提供了示例性化合物1、化合物10、化合物11、化合物17、化合物49和化合物114的制备方法,如下所述。
实施例1
化合物1的合成:
中间体M1的合成
Figure BDA0002355214860000211
中间体M1的合成:氮气氛围下,于300mL无水甲苯(Tol)中依次加入对氰基苯胺(6.50g,55mmol),4-溴苯腈(10.00g,55mmol),t-BuONa(10.60g,110mmol),Pd2(dba)3(504mg,0.55mmol),S-Phos(2-二环己基膦-2',6'-二甲氧基联苯,452mg,1.1mmol),除氧10min后,升温至80℃,反应24h,冷却并抽滤,收集滤液,加水、二氯甲烷萃取分液,收集有机相并用无水硫酸钠干燥,旋除溶剂,经柱层析纯化,得白色固体(9.04g,75%)。
MALDI-TOF:m/z:计算值:C14H9N3:219.24,实测值:218.70。
1H NMR(400MHz,CDCl3)δ7.48(d,J=8.6Hz,4H),6.97(d,J=8.7Hz,4H),6.10(s,1H)。
中间体M2-1的合成:
Figure BDA0002355214860000212
中间体M2-1的合成:氮气条件下,于100mL无水甲苯中依次加入1,3-二溴-5-氯苯(2.00g,7.41mmol),咔唑(2.60g,15.56mmol),t-BuONa(2.85g,29.64mmol),Pd2(dba)3(339mg,0.37mmol),P(t-Bu)3HBF4(457mg,1.11mmol),除氧10min后,升温至80℃,反应4h,变为棕黑色溶液。待反应完成,冷却并抽滤,收集滤液,加水、DCM萃取,收集有机相并用无水Na2SO4干燥,旋除溶剂,经柱层析纯化(石油醚/DCM,8/1,V/V),得M2-1白色固体(2.46g,75%)。
MALDI-TOF m/z:计算值:C30H19ClN2:442.94,实测值:442.42。
1H NMR(400MHz,CDCl3)δ8.15(d,J=7.7Hz,4H),7.76(s,1H),7.72(s,2H),7.55(d,J=8.2Hz,4H),7.46(t,J=7.6Hz,4H),7.33(t,J=7.4Hz,4H)。
化合物1的合成:
Figure BDA0002355214860000221
化合物1的合成:氮气条件下,100mL无水甲苯中依次加入M2-1(1.05g,2.37mmol),M1(623mg,2.84mmol),t-BuONa(910mg,9.48mmol),Pd2(dba)3(109mg,0.12mmol),P(t-Bu)3HBF4(104mg,0.36mmol),除氧10min后,升温至110℃,反应24h,变为棕黑色溶液。待反应完成,冷却并抽滤,收集滤液,加水、DCM萃取分液得棕色有机相。收集的有机相用无水Na2SO4干燥,旋除溶剂,经柱层析纯化得白色固体(1.05g,71%)。
MALDI-TOF:m/z:计算值:C44H27N5:625.72,实测值:625.02.
1H NMR(400MHz,CDCl3)δ8.13(d,J=7.7Hz,4H),7.60(s,1H),7.51(d,J=8.2Hz,4H),7.49(d,J=8.5Hz,4H),7.48(d,J=8.6Hz,4H),7.44(t,J=7.9Hz,4H),7.40(s,2H),6.97(d,J=8.7Hz,4H)。
化合物1的元素分析结果:计算值:C44H27N5(%):C 84.46,H 4.35,N11.19;实测值:C 84.36,H 4.40,N 11.24。
实施例2
化合物10的合成:
中间体M2-10的合成:
Figure BDA0002355214860000231
中间体M2-10的合成:氮气条件下,于100mL无水甲苯中依次加入1,3-二溴-5-氯苯(2.00g,7.41mmol),吩噁嗪(2.85g,15.56mmol),t-BuONa(2.85g,29.64mmol),Pd2(dba)3(339mg,0.37mmol),P(t-Bu)3HBF4(457mg,1.11mmol),除氧10min后,升温至80℃,反应4h,变为棕黑色溶液。待反应完成,冷却并抽滤,收集滤液,加水、DCM萃取,收集有机相并用无水Na2SO4干燥,旋除溶剂,经柱层析纯化(石油醚/DCM,8/1,V/V),得M2-10白色固体(2.68g,76%)。
MALDI-TOF m/z:计算值:C30H19ClN2O2:474.94,实测值:474.50。1H NMR(400MHz,CDCl3)δ7.51(s,2H),7.29(d,J=7.4Hz,4H),7.20–7.16(m,5H),7.10(t,J=7.4Hz,4H),7.08–6.99(m,4H)
化合物10的合成:
Figure BDA0002355214860000232
化合物10的合成:氮气条件下,100mL无水甲苯中依次加入M2-10(1.13g,2.37mmol),M1(623mg,2.84mmol),t-BuONa(910mg,9.48mmol),Pd2(dba)3(109mg,0.12mmol),P(t-Bu)3HBF4(104mg,0.36mmol),除氧10min后,升温至110℃,反应24h,变为棕黑色溶液。待反应完成,冷却并抽滤,收集滤液,加水、DCM萃取分液得棕色有机相。收集的有机相用无水Na2SO4干燥,旋除溶剂,经柱层析纯化得白色固体(1.09g,70%)。
MALDI-TOF:m/z:计算值:C44H27N5O2:657.72,实测值:657.50.
1H NMR(400MHz,CDCl3)δ7.58(s,1H)7.49–7.45(m,6H),7.38(t,J=7.8Hz,4H),7.19(d,J=8.5Hz,4H),7.14–7.08(m,4H),6.97(d,J=8.7Hz,4H),6.69(s,2H),6.08(s,2H)。
化合物10的元素分析结果:计算值:C44H27N5(%):C 80.35,H 4.14,N10.65;实测值:C 80.26,H 4.20,N 10.68。
实施例3
化合物11的合成:
中间体M2-11的合成:
Figure BDA0002355214860000241
中间体M2-11的合成与中间体M2-10的合成类似,得M2-11白色固体(2.74g,73%)。
MALDI-TOF m/z:计算值:C30H19ClN2S2:507.07,实测值:506.97。
1H NMR(400MHz,CDCl3)δ7.34(s,2H)7.19(d,J=7.4Hz,4H),7.16–7.12(m,5H),7.07(t,J=7.4Hz,4H),7.02–6.99(m,4H)。
化合物10的合成:
Figure BDA0002355214860000242
化合物11的合成与化合物10的合成类似,得白色固体(1.11g,68%)。
MALDI-TOF:m/z:计算值:C44H27N5S2:689.85,实测值:689.54.
1H NMR(400MHz,CDCl3)δ7.63(s,1H),7.45(td,J=8.6Hz,6H),7.35(t,J=7.7Hz,4H),7.18(t,J=8.5Hz,4H),7.10–7.06(m,4H),7.00(t,J=7.4Hz,4H),6.93(d,J=7.6Hz,2H),6.59(s,2H)。
化合物11的元素分析结果:计算值:C44H27N5(%):C 76.61,H 3.94,N10.15实测值:C 76.55,H 3.99,N 10.10。
实施例4
化合物17的合成:
Figure BDA0002355214860000251
化合物17的合成:氮气条件下,100mL无水甲苯中依次加入M2-1(1.05g,2.37mmol),双(4-吡啶-4-基-苯基)-胺(917mg,2.84mmol),t-BuONa(910mg,9.48mmol),Pd2(dba)3(109mg,0.12mmol),P(t-Bu)3HBF4(104mg,0.36mmol),除氧10min后,升温至110℃,反应24h,变为棕黑色溶液。待反应完成,冷却并抽滤,收集滤液,加水、DCM萃取分液得棕色有机相。收集的有机相用无水Na2SO4干燥,旋除溶剂,经柱层析纯化得白色固体(1.44g,83%)。
MALDI-TOF:m/z:计算值:C52H35N5:729.87,实测值:729.53。
1H NMR(400MHz,CDCl3)δ8.68(d,J=7.3Hz,4H),8.39-8.33(m,4H),8.13(d,J=7.7Hz,4H),7.60(s,1H),7.51(d,J=8.2Hz,4H),7.49(d,J=8.5Hz,4H),7.48-7.44(m,8H),7.40(s,2H),6.97(d,J=8.7Hz,4H)。
化合物17的元素分析结果:计算值:C52H35N5(%):C 85.57,H 4.83,N9.60;实测值:C 85.50,H 4.88,N 9.62。
实施例5
化合物49的合成:
Figure BDA0002355214860000252
中间体M3-1的合成与M2-1的合成类似,得白色固体(2.57g,78%)。
MALDI-TOF m/z:计算值:C29H18ClN3:443.93,实测值:443.52。
1H NMR(400MHz,CDCl3)δ8.18(d,J=7.7Hz,4H),7.82(s,2H),7.64(d,J=8.2Hz,4H),7.54(t,J=7.6Hz,4H),7.39(t,J=7.4Hz,4H)。
化合物49的合成与化合物17的合成类似,得白色固体(1.53g,88%)。
MALDI-TOF:m/z:计算值:C51H34N6:730.86,实测值:730.49。
1H NMR(400MHz,CDCl3)δ8.73(d,J=7.2Hz,4H),8.44-8.39(m,4H),8.17(d,J=7.8Hz,4H),7.69(d,J=8.2Hz,4H),7.51-7.47(m,8H),7.44(t,J=8.5Hz,4H),7.40(s,2H),6.98(d,J=8.7Hz,4H)。
化合物49的元素分析结果:计算值:C51H34N6(%):C 83.81,H 4.69,N11.50;实测值:C 83.77H 4.72,N 11.51。
实施例6
化合物114的合成:
中间体M4的合成:
Figure BDA0002355214860000261
化合物M4-A的合成:氮气条件下,于100mL无水DMF中依次加入1-溴-3-氯-5-碘苯(2.35g,7.41mmol),咔唑(1.24g,7.41mmol),K2CO3(4.09g,29.64mmol),CuI(70mg,0.37mmol),1,10-Phen(200mg,1.11mmol),除氧10min后,升温至80℃,反应12h,变为棕黑色溶液。待反应完成,冷却并抽滤,收集滤液,加水、DCM萃取,收集有机相并用无水Na2SO4干燥,旋除溶剂,经柱层析纯化(石油醚/DCM,12/1,V/V),得M4-A(2.12g,80%)。
MALDI-TOF m/z:计算值:C18H11BrClN:356.64,实测值:356.21。
1H NMR(400MHz,CDCl3)δ8.15(d,J=7.7Hz,2H),7.76(s,1H),7.68(s,2H),7.55-7.49(m,4H),7.29(t,J=7.4Hz,2H)。
中间体M4的合成与中间体M2-1、10、11的合成类似,得M4(2.59g,70%)。
MALDI-TOF m/z:计算值:C30H19ClN2S:475.00,实测值:469.87。
1H NMR(400MHz,CDCl3)δ7.34(s,2H)7.26-7.19(m,4H),7.16–7.12(m,5H),7.09(t,J=7.4Hz,4H),7.02–6.99(m,4H)。
化合物114的合成:
Figure BDA0002355214860000271
化合物114的合成与化合物1、10、11的合成类似,得白色固体(1.09g,75%)。
MALDI-TOF:m/z:计算值:C44H27N5S:657.78,实测值:657.23。
1H NMR(400MHz,CDCl3)δ7.64(s,1H),7.47-7.44(m,6H),7.37(t,J=7.7Hz,4H),7.19(t,J=8.5Hz,4H),7.09–7.06(m,4H),6.99-6.93(m,6H),6.61(s,2H)。
化合物114元素分析结果:计算值:C44H27N5S(%):C 80.34,H 4.14,N10.65;实测值:C 80.29,H 4.10,N 10.69。
运用密度泛函理论(DFT),针对化合物1、化合物10、化合物11、化合物17、化合物49和化合物114,利用Gaussian 09程序包在B3LYP/6-31G(d)计算水平下,优化并计算得到了分子前线轨道HOMO和LUMO的分布情况;同时基于含时密度泛函理论(TDDFT),模拟计算了分子的单线态能级S1和三线态能级T1。
化合物1、化合物10、化合物11、化合物17、化合物49和化合物114的HOMO、LUMO等参数的计算值及Tg的测试值结果如表1所示。
表1化合物的性能参数
Figure BDA0002355214860000272
Figure BDA0002355214860000281
注:S1表示单线态能级,T1表示三线态能级,Tg表示玻璃化转变温度。
由表1可以看出,本发明的化合物具有高的单线态和三线态能级,适于作为发光层中的主体材料。另外,本发明的化合物还具有较高玻璃化转变温度,有利于在器件制备中形成稳定的薄膜,提高器件的稳定性。
根据本发明的化合物的一种实施方式,所述化合物的单重态能级S1高于所述客体材料的单重态能级S1,所述主体材料的三重态能级T1高于所述客体材料的三重态能级T1。
本发明还提供一种显示面板,所述显示面板包括有机发光器件,其中所述有机发光器件包括相对设置的阳极、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化合物中的一种或一种以上。
根据本发明的显示面板的一种实施方式,所述发光层的发光材料包括主体材料和客体材料,所述主体材料为本发明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种实施方式,所述发光层包括红色发光层,所述主体材料为红光主体材料。
根据本发明的显示面板的一种实施方式,所述发光层包括绿色发光层,所述主体材料为绿光主体材料。
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。
空穴注入材料、空穴传输材料及电子阻挡材料可选自2,2'-二甲基-N,N'-二-1-萘基-N,N'-二苯基[1,1'-联苯]-4,4'-二胺(α-NPD)、4,4',4”-三(咔唑-9-基)三苯胺(TCTA)、1,3-二咔唑-9-基苯(mCP)、4,4'-二(9-咔唑)联苯(CBP)、3,3'-二(N-咔唑基)-1,1'-联苯(mCBP)、2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(HATCN)、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺(TAPC)、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPB)、N,N'-二(萘-2-基)-N,N'-二(苯基)联苯-4,4'-二胺(NPB)、聚(3,4-乙烯二氧噻吩)-聚苯乙烯磺酸(PEDOT:PSS)、聚乙烯咔唑(PVK)、9-苯基-3,9-联咔唑(CCP)、三氧化钼(MoO3)等材料,但不局限于以上几种材料。
空穴阻挡材料、电子传输材料、电子注入材料可选自2,8-二(二苯基氧膦基)二苯并噻吩(PPT)、TSPO1、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯(TPBi)、2,8-双(二苯基膦氧基)二苯并呋喃(PPF)、二(2-二苯氧化膦基)二苯醚(DPEPO)、氟化锂(LiF)、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶(B3PYMPM)、4,7-二苯基-1,10-菲啰啉(Bphen)、1,3,5-三[(3-吡啶基)-3-苯基]苯(TmPyBP)、三[2,4,6-三甲基-3-(3-吡啶基)苯基]硼烷(3TPYMB)、1,3-双(3,5-二吡啶-3-基苯基)苯(B3PYPB)、1,3-双[3,5-二(吡啶-3-基)苯基]苯(BMPYPHB)、2,4,6-三(联苯基-3-基)-1,3,5-三嗪(T2T)、二苯基二[4-(吡啶-3-基)苯基]硅烷(DPPS)、碳酸铯(Cs2O3)、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝(BAlq)、8-羟基喹啉-锂(Liq)、三(8-羟基喹啉)铝(Alq3)等材料,但不局限于以上几种材料。
在本发明提供的显示面板的一个实施方式中,所述发光层包括主体材料和客体材料,主体材料选自2,8-二(二苯基氧膦基)二苯并噻吩、4,4'-二(9-咔唑)联苯、3,3'-二(N-咔唑基)-1,1'-联苯、2,8-双(二苯基膦氧基)二苯并呋喃、双(4-(9H-咔唑基-9-基)苯基)二苯硅烷、9-(4-叔丁基苯基)-3,6-双(三苯基甲硅烷基)-9H-咔唑、二(2-二苯氧化膦基)二苯醚、1,3-双[3,5-二(吡啶-3-基)苯基]苯、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶、9-(3-(9H-咔唑基-9-基)苯基)-9H-咔唑-3-氰基、9-苯基-9-[4-(三苯基硅烷基)苯基]-9H-芴、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯、二苯基[4-(三苯基硅烷基)苯基]氧膦、4,4',4”-三(咔唑-9-基)三苯胺、2,6-二咔唑-1,5-吡啶、聚乙烯基咔唑和聚芴中的任意一种或一种以上,客体材料可选自荧光材料、磷光材料或热活化延迟荧光材料和聚集诱导发光材料中的一种或一种以上。
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。
在本发明提供的显示面板中,有机发光器件如图2示意性地示出,其包括:基板1、ITO阳极2、空穴注入层3、第一空穴传输层4、第二空穴传输层5、发光层6、第一电子传输层7、第二电子传输层8、阴极9(银电极)。
有机发光器件可以按照本领域公知的方法进行制作,在此不再详述。在本发明中,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。
下面具体介绍本发明的显示面板中的有机发光器件的一种制备方法。
实施例7
本实施例提供一种有机发光器件,器件结构为:
ITO(10nm)/HAT-CN(10nm)/NPB(40nm)/TAPC(10nm)/化合物1:Ir(MDQ)2(acac)(20nm)/TPBi(30nm)/LiF(2nm)/Al(100nm)。
在上述器件结构中,ITO作为阳极材料;HAT-CN用作空穴注入层材料,NPB和TAPC分别用作第一、第二空穴传输层材料;发光层由客体材料(Ir(MDQ)2(acac))以一定比例掺杂到主体材料(化合物1)中;TPBi作为电子传输层材料;LiF作为电子注入层材料;Al作为阴极材料。
具体制备步骤如下:
1)将玻璃基板1切成50mm×50mm×0.7mm的大小,分别在丙酮、异丙醇和去离子水中超声清洁30分钟,然后将其在UV臭氧下清洁30分钟来进行清洁。将所得的厚度为10nm的氧化铟锡(ITO)阳极1的玻璃基板安装到真空沉积设备上;
2)在ITO阳极层2上,通过真空蒸镀方式蒸镀空穴注入层材料HAT-CN作为空穴注入层3,厚度为10nm;
3)在空穴注入层3上真空蒸镀空穴传输层材料NPB作为第一空穴传输层4,厚度为40nm;
4)在第一空穴传输层4上真空蒸镀空穴传输型材料TAPC作为第二空穴传输层5,厚度为10nm;
5)第二空穴传输层5上真空蒸镀一层发光层6,厚度为20nm;其中,本发明的化合物1作为主体材料,Ir(MDQ)2(acac)作为掺杂材料(客体材料),掺杂比例为3%(质量比)6;
6)在发光层6上真空蒸镀电子传输型材料TPBi作为电子传输层7,厚度为30nm;
7)电子传输层6上真空蒸镀电子传输材料LiF作为电子注入层8,厚度为2nm;
8)电子传输层8上真空蒸镀铝(Al)电极作为阴极9,厚度为100nm。
OLED器件的制备过程中使用的化合物的结构如下:
Figure BDA0002355214860000311
实施例8
本实施例与实施例7的区别在于,将化合物1替换为化合物10。
实施例9
本实施例与实施例7的区别在于,将化合物1替换为化合物11。
实施例10
本实施例与实施例7的区别在于,将化合物1替换为化合物17。
实施例11
本实施例与实施例7的区别在于,将化合物1替换为化合物49。
实施例12
本实施例与实施例7的区别在于,将化合物1替换为化合物114。
对比例1
本对比例与实施例7的区别在于,将化合物1替换为化合物mCP。
Figure BDA0002355214860000321
有机电致发光器件性能见表2。
表2
Figure BDA0002355214860000322
Figure BDA0002355214860000331
由表2可知,本发明提供的有机发光器件具有较低的驱动电压、以及较高的发光效率,其中驱动电压小于3.50V,电流效率(CE(max))大于20cd/A,功率效率(PE(max))大于18lm/W。相对于对比器件1,性能均具有明显的提升,这主要得益于本发明的材料具有同时传输空穴和电子的双极性特征,这样的化合物有利于发光层中的电荷传输平衡,可拓宽激子复合区域,提高器件效率。
本发明还提供了一种显示装置,其包括如上文所述的有机发光显示面板。显示装置可以是手机显示屏、电脑显示屏、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3是根据本发明实施例提供的一种显示装置的示意图。在图3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。

Claims (7)

1.一种化合物,所述化合物具有化学式1所示的化学结构:
Figure FDA0003367941610000011
其中,Ar1、Ar2、Ar3和Ar4均为氢原子,n1、n2、n3、n4均为1;
R1和R2各自独立地选自不存在、-O-、-S-;当R1和R2选自不存在时,化学式1中虚线-----表示单键;当R1和R2各自独立地选自-O-、-S-时,化学式1中虚线-----不存在;
X1、X2和X3各自独立地选自C原子或N原子;
L1和L2均为亚苯基;
Y1和Y2各自独立地选自#-CN、
Figure FDA0003367941610000012
中的一种;
#表示在化学式1中的连接位置。
2.根据权利要求1所述的化合物,其特征在于,Y1和Y2选自相同的基团。
3.根据权利要求1所述的化合物,其特征在于,所述化合物选自下列化合物:
Figure FDA0003367941610000021
Figure FDA0003367941610000031
4.一种显示面板,包括有机发光器件,所述有机发光器件包括相对设置的阳极、阴极,以及位于阳极和阴极之间的发光层,其中发光层包括主体材料和客体材料,其特征在于,所述发光层的主体材料为权利要求1至3任一项所述的化合物中的一种或多种。
5.根据权利要求4所述的显示面板,其特征在于,所述主体材料的单重态能级S1高于所述客体材料的单重态能级S1,所述主体材料的三重态能级T1高于所述客体材料的三重态能级T1。
6.根据权利要求4或5所述的显示面板,其特征在于,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。
7.一种显示装置,包括权利要求4至6任一项所述的显示面板。
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