CN112266379A - 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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- CN112266379A CN112266379A CN202011193272.XA CN202011193272A CN112266379A CN 112266379 A CN112266379 A CN 112266379A CN 202011193272 A CN202011193272 A CN 202011193272A CN 112266379 A CN112266379 A CN 112266379A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 101
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 20
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 53
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- 239000007924 injection Substances 0.000 claims description 14
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
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- 230000009286 beneficial effect Effects 0.000 abstract description 5
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Abstract
本发明属于OLED技术领域且提供了化学式1所示的化合物,其中,X选自氧原子、硫原子、‑C(RaRb)‑、‑N(Ra)‑、‑PO(Ph)‑、‑PS(Ph)‑、‑SO2‑、‑Si(RaRb)‑,或者X与相邻的碳原子形成单键;Ra和Rb独立地为C6‑C30芳基、C2‑C30杂芳基、C1‑C20烷基/烷氧基/烷硫基、C3‑C20环烷基;X1‑X8各自独立地选自碳原子或氮原子;L1和L2各自独立地选自共价单键、C6‑C30亚芳基,C3‑C30亚杂芳基;R1和R2独立地为氢原子、C1‑C20烷基、C1‑C20烷氧基、C1‑C20烷硫基、C3‑C20环状烷基、C6‑C40芳基、C3‑C40杂芳基;n1和n2为0、1、2、3。本发明的化合物具有D‑A‑D型结构,可同时传输电子和空穴,有利于扩宽激子复合区域,提升器件效率。螺环结构有效降低分子间作用,有利于降低化合物的结晶性,提高器件的稳定性。本发明还提供一种显示面板和显示装置。
Description
技术领域
本发明属于OLED技术领域,具体涉及一种化合物以及包含该化合物的显示面板和显示装置。
背景技术
有机电致发光显示(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器件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OLED器件。
由于重金属磷光材料有较长的寿命(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,重金属磷光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。
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OLED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:
其中,在化学式1中,X选自氧原子、硫原子、-C(RaRb)-、-N(Ra)-、-PO(Ph)-、-PS(Ph)-、-SO2-、-Si(RaRb)-,或者X与相邻的碳原子形成单键;Ra和Rb各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C1-C20烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C1-C20烷硫基、取代或未取代的C3-C20环烷基;
X1-X8各自独立地选自碳原子或氮原子;
L1和L2各自独立地选自共价单键、取代或未取代的C6-C30亚芳基,取代或未取代的C3-C30亚杂芳基;
R1和R2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C1-C20烷氧基、取代或未取代的C1-C20烷硫基、取代或未取代的C3-C20环状烷基、取代或未取代的C6-C40芳基、取代或未取代的C3-C40杂芳基;n1和n2各自独立地选自0、1、2、3。
本发明提供了一系列D-A-D型的磷光双极性主体材料,可以同时传输电子及空穴,有利于扩宽激子复合区域,从而提升效率;在D-A-D骨架下方的螺环有效地降低了分子间作用,有利于降低化合物的结晶性。本发明的有机化合物可以作为OLED发光器件中蓝光主体材料使用,其具有较高的三线态能级ET和较为合适的HOMO/LUMO能级,可以将能量高效地传递给客体材料并防止能量倒流。另外,化合物具有较高的玻璃化温度和热稳定性,易于在器件中形成无定形的薄膜,有利于器件的稳定性。在D-A-D骨架中引入的螺环结构可以降低分子间的作用力,使得分子的堆叠降低,有利于降低分子间浓度猝灭。本发明的化合物能够有效提高器件的发光效率并延长器件寿命,在OLED器件技术领域中可以得到很好的应用。
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:
其中,在化学式1中,X选自氧原子、硫原子、-C(RaRb)-、-N(Ra)-、-PO(Ph)-、-PS(Ph)-、-SO2-、-Si(RaRb)-,或者X与相邻的碳原子形成单键;Ra和Rb各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C1-C20烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C1-C20烷硫基、取代或未取代的C3-C20环烷基;
X1-X8各自独立地选自碳原子或氮原子;
L1和L2各自独立地选自共价单键、取代或未取代的C6-C30亚芳基,取代或未取代的C3-C30亚杂芳基;
R1和R2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C1-C20烷氧基、取代或未取代的C1-C20烷硫基、取代或未取代的C3-C20环状烷基、取代或未取代的C6-C40芳基、取代或未取代的C3-C40杂芳基;n1和n2各自独立地选自0、1、2、3。
在本发明的化合物中,取代基R1和R2连接给电子单元,而含有SO2的稠环母核结构作为受电子单元。在含有SO2的母核的连接给电子基团R1和R2,可以使化合物具有同时传输空穴和电子的能力,从而更易使载流子传输达到平衡,同时这种双极性传输也会使载流子复合区域更易处于发光层,进一步提升发光效率。
根据本发明所述化合物一种实施方式,X选自氧原子、硫原子、-C(RaRb)-、-N(Ra)-,或者X与相邻的碳原子形成单键。进一步地,X选自氧原子、硫原子、或者X与相邻的碳原子形成单键。
根据本发明所述化合物一种实施方式,所述化合物具有式1-1至式1-6所示的结构:
根据本发明所述化合物一种实施方式,所述化合物选自式1-1到式1-4表示的化合物。
进一步地,所述化合物选自由式1-1、式1-3或1-4表示的化合物。式1-1、1-3、1-4,这样的连接方式可能更易使之形成分子内、分子间C-H…N键,使得易于断裂的碳氮(C-N)键得到加强,分子的键解离能可能得到提升,使其在器件制备中更稳定,有利于提高器件的寿命。
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;m、n、p选自0、1或2;
U1、U2、U3和U4各自独立地选自氢原子、C1-C6烷基、C6-C18芳基、C4-C20杂芳基;当Z为氧原子或硫原子时,p为0;
#、#1、#2表示可能的连接位置。
根据本发明所述化合物一种实施方式,
R1和R2各自独立地选自以下基团中的任意一种:
在本实施例的化合物,R1和R2基团中的氮原子均被其他基团取代(非-NH),这种结构可以提高基团的稳定性,继而延长有机发光分子和有机发光器件的使用寿命。
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;m、n、q选自0、1或2;
U1、U2、U3和U4各自独立地选自氢原子、C1-C6烷基、C6-C18芳基、C4-C20杂芳基;
当Z为氧原子或硫原子时,p为0;
#、#1、#2表示可能的连接位置。。
根据本发明所述化合物一种实施方式,R1和R2各自独立地选自以下基团中的任意一种:
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;X选自C原子、N原子、O原子、S原子;m、n、p和q选自0、1或2;
U1、U2、U3和U4各自独立地选自氢原子、C1-C6烷基、C6-C18芳基、C4-C20杂芳基;
当Z或X为氧原子或硫原子时,p或q为0;
#表示可能的连接位置。
根据本发明所述化合物一种实施方式,R1和R2各自独立地选自以下基团中的任意一种:
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的任意一种:
本发明的化合物可以用作发光主体材料,也可以用作TADF材料、电子传输层(ETL)材料或空穴阻挡层(HBL)材料。
本发明还提供了示例性的编号为化合物1至化合物9的制备方法,如下所述。
实施例1
化合物1的制备
步骤(1)
在氮气氛围下,于60mL无水四氢呋喃(THF)中加入反应物a-1(5mmol),在-78℃下将n-BuLi(5mmol)逐滴加入,待滴加结束,保持-78℃下反应2h;将化合物A(5mmol)溶解到无水THF中,随后滴加到反应液中,继续低温反应1h,随后升温到室温反应过夜。待反应结束,加少量水淬灭,加入二氯甲烷/水(DCM/H2O)进行萃取,收集有机相并用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂得到粗品。
将上述粗品于氮气条件下加入到30mL的醋酸中,搅拌加热,于120℃下回流(reflux)反应2h,随后加入3mL盐酸,于此温度下加热反应12h。待反应结束,冷却并进行萃取,收集有机相并旋除溶剂,经柱层析纯化,得到中间体B1(收率67%)。
MALDI-TOF:m/z:计算值:C26H16O:344.12,实测值:344.31。
步骤(2)
在氮气氛围下,于60mL无水THF中加入反应物a-3(5mmol),在-78℃下将n-BuLi(5mmol)逐滴加入,待滴加结束,保持-78℃下反应2h;将化合物B1(5mmol)溶解到无水THF中,随后滴加到反应液中,继续低温反应1h,随后升温到室温反应过夜。待反应结束,加少量水淬灭,加DCM/H2O进行萃取,收集有机相并用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂得到粗品;
将上述粗品于氮气条件下加入到30mL的醋酸中,搅拌加热,于120℃下回流(reflux)反应2h,随后加入3mL盐酸,于此温度下加热反应12h。待反应结束,冷却并进行萃取,收集有机相并旋除溶剂,经柱层析纯化,得到中间体C1(收率75%)。
MALDI-TOF:m/z:计算值:C38H24S:512.16,实测值:512.35。
步骤(3)
在氮气氛围下,在冰浴中于40mL醋酸中加入反应物C1(4mmol),后续加入Br2(8.8mmol),冰浴条件下反应2h,随后在室温下反应过夜。待反应结束,加入DCM/H2O进行萃取,收集有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到中间体D1(收率85%)。
MALDI-TOF:m/z:计算值:C38H22Br2S:667.98,实测值:668.20。
步骤(4)
于100mL反应瓶中加入40mL冰醋酸及反应中间体D1(4mmol),随后搅拌,缓慢加入约8mL的30%双氧水,加热回流,反应过夜。待反应完成后,冷却至室温,加二氯甲烷/H2O进行萃取,将收集到的有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到中间体E1(收率90%)。
MALDI-TOF:m/z:计算值:C38H22Br2O2S:699.97,实测值:700.19。
步骤(5)
在氮气氛围下,于250mL反应瓶中加入约100mL 1,4-二氧六环(1,4-dioxane)溶剂,然后依次加入K2CO3(2.5mmol)水溶液,中间化合物E1(1mmol),反应物1(2.2mmol),以及Pd(PPh3)4(0.05mmol),升温至100℃,反应过夜。待反应完成后,冷却至室温,加二氯甲烷/H2O进行萃取,将收集到的有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到化合物1(收率80%)。
MALDI-TOF:m/z:计算值:C74H46N2O2S:1026.33,实测值:1026.53。
化合物元素分析结果:计算值:C74H46N2O2S(%):C 86.52,H 4.51,N 2.73;测试值:C 86.51,H 4.50,N 2.75。
实施例2
化合物2的制备
该化合物2的制备方法与实施例1的区别仅在于,将实施例1的步骤(5)中的反应物1用等摩尔量的反应物2替换,其他原料、反应步骤以及反应条件与实施例1相同,最后得到化合物2(收率78%)。
MALDI-TOF:m/z:计算值:C72H44N4O2S:1028.32,实测值:1028.51。
化合物元素分析结果:计算值:C72H44N4O2S(%):C 84.02,H 4.31,N 5.44;测试值:C 84.01,H 4.30,N 5.46。
实施例3
化合物3的制备
该化合物3的制备方法与实施例1的区别仅在于,将实施例1的步骤(5)中的反应物1用等摩尔量的反应物3替换,其他原料、反应步骤以及反应条件与实施例1相同,最后得到化合物3(收率75%)。
MALDI-TOF:m/z:计算值:C70H42N6O2S:1030.31,实测值:1030.50。
化合物元素分析结果:计算值:C70H42N6O2S(%):C 81.53,H 4.11,N 8.15;测试值:C 81.52,H 4.10,N 8.17。
实施例4
化合物4的制备
该化合物4的制备方法与实施例1的区别仅在于,将实施例1的步骤(5)中的反应物1用等摩尔量的反应物4替换,其他原料、反应步骤以及反应条件与实施例1相同,最后得到化合物4(收率81%)。
MALDI-TOF:m/z:计算值:C74H46N2O2S:1026.33,实测值:1026.54。
化合物元素分析结果:计算值:C74H46N2O2S(%):C 86.52,H 4.51,N 2.73;测试值:C 86.51,H 4.50,N 2.75。
实施例5
化合物5的制备
步骤(1)
该中间体B2的制备方法与实施例1中间体B1的区别仅在于,将实施例1的步骤(1)中的反应物a-1用等摩尔量的反应物a-2替换,其、反应步骤、原料以及反应条件与实施例1相同,最后得到中间体B2(收率65%)。
MALDI-TOF:m/z:计算值:C27H20O2:376.15,实测值:376.34。
步骤(2)
该中间体C2的制备方法与实施例1中间体C1的区别仅在于,将实施例1的步骤(2)中的中间体B1用等摩尔量的中间体B2替换,其反应步骤、原料以及反应条件与实施例1相同,最后得到中间体C2(收率73%)。
MALDI-TOF:m/z:计算值:C38H24OS:528.15,实测值:528.34。
步骤(3)
在氮气氛围下,在冰浴中于40mL醋酸中加入反应物C2(4mmol),后续加入Br2(8.8mmol),冰浴条件下反应2h,随后在室温下反应过夜。待反应结束,加入DCM/H2O进行萃取,收集有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到中间体D2(收率84%)。
MALDI-TOF:m/z:计算值:C38H22Br2OS:683.98,实测值:684.17。
步骤(4)
于100mL反应瓶中加入40mL冰醋酸及反应中间体D2(4mmol),随后搅拌,缓慢加入约8mL的30%双氧水,加热回流,反应过夜。待反应完成后,冷却至室温,加二氯甲烷/H2O进行萃取,将收集到的有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到中间体E2(收率89%)。
MALDI-TOF:m/z:计算值:C38H22Br2O3S:715.97,实测值:716.20。
步骤(5)
在氮气氛围下,于250mL反应瓶中加入约100mL 1,4-二氧六环溶剂,然后依次加入K2CO3(2.5mmol)水溶液,中间化合物E2(1mmol),反应物1(2.2mmol),以及Pd(PPh3)4(0.05mmol),升温至100℃,反应过夜。待反应完成后,冷却至室温,加二氯甲烷/H2O进行萃取,将收集到的有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到化合物5(收率79%)。
MALDI-TOF:m/z:计算值:C74H46N2O3S:1042.32,实测值:1042.51。
化合物元素分析结果:计算值:C74H46N2O3S(%):C 85.20,H 4.44,N 2.69;测试值:C 85.19,H 4.43,N 2.70。
实施例6
化合物6的制备
该化合物6的制备方法与实施例5的区别仅在于,将实施例5的步骤(5)中的反应物1用等摩尔量的反应物2替换,其反应步骤、原料以及反应条件与实施例5相同,最后得到化合物6(收率77%)。
MALDI-TOF:m/z:计算值:C72H44N4O3S:1044.31,实测值:1044.50。
化合物元素分析结果:计算值:C72H44N4O3S(%):C 82.74,H 4.24,N 5.36;测试值:C 82.73,H 4.23,N 5.38。
实施例7
化合物7的制备
该化合物7的制备方法与实施例5的区别仅在于,将实施例5的步骤(5)中的反应物1用等摩尔量的反应物3替换,其他原料、反应步骤以及反应条件与实施例5相同,最后得到化合物7(收率74%)。
MALDI-TOF:m/z:计算值:C70H42N6O3S:1046.30,实测值:1046.51。
化合物元素分析结果:计算值:C70H42N6O3S(%):C 80.29,H 4.04,N 8.03;测试值:C 80.28,H 4.03,N 8.05。
实施例8
化合物8的制备
步骤(1)
该中间体B3的制备方法与实施例1中间体B1的区别仅在于,将实施例1的步骤(1)中的反应物a-1用等摩尔量的反应物a-3替换,其他原料、反应步骤以及反应条件与实施例1相同,最后得到中间体B3(收率64%)。
MALDI-TOF:m/z:计算值:C26H16OS:376.09,实测值:376.28。
步骤(2)
在氮气氛围下,在冰浴中于40mL醋酸中加入反应物中间体B3(4mmol),后续加入Br2(8.8mmol),冰浴条件下反应2h,随后在室温下反应过夜。待反应结束,加入DCM/H2O进行萃取,收集有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到中间体C3(收率87%)。
MALDI-TOF:m/z:计算值:C26H14Br2OS:531.91,实测值:532.10。
步骤(3)
于100mL反应瓶中加入40mL冰醋酸及反应中间体C3(4mmol),随后搅拌,缓慢加入约8mL的30%双氧水,加热回流,反应过夜。待反应完成后,冷却至室温,加二氯甲烷/H2O进行萃取,将收集到的有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到中间体D3(收率92%)。
MALDI-TOF:m/z:计算值:C26H14Br2O3S:563.90,实测值:564.11。
步骤(4)
在氮气氛围下,于60mL无水THF中加入反应物a-3(2mmol),在-78℃下将n-BuLi(2mmol)逐滴加入,待滴加结束,保持-78℃下反应2h;将中间化合物D3(2mmol)溶解到无水THF中,随后滴加到反应液中,继续低温反应1h,随后升温到室温反应过夜。待反应结束,加少量水淬灭,加DCM/H2O进行萃取,收集有机相并用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂得到粗品;
将上述粗品于氮气条件下加入到30mL的醋酸中,搅拌加热,于120℃下回流(reflux)反应2h,随后加入3mL盐酸,于此温度下加热反应12h。待反应结束,冷却并进行萃取,收集有机相并旋除溶剂,经柱层析纯化,得到中间体E3(收率60%)。
MALDI-TOF:m/z:计算值:C38H22Br2O2S2:731.94,实测值:732.13。
步骤(5)
在氮气氛围下,于250mL反应瓶中加入约100mL 1,4-二氧六环溶剂,然后依次加入K2CO3(2.5mmol)水溶液,中间化合物E3(1mmol),反应物1(2.2mmol),以及Pd(PPh3)4(0.05mmol),升温至100℃,反应过夜。待反应完成后,冷却至室温,加二氯甲烷/H2O进行萃取,将收集到的有机相用无水Na2SO4干燥,抽滤收集滤液、旋除溶剂并进行柱层析纯化,得到化合物8(收率78%)。
MALDI-TOF:m/z:计算值:C74H46N2O2S2:1058.30,实测值:1058.51。
化合物元素分析结果:计算值:C74H46N2O2S2(%):C 83.90,H 4.38,N 2.64;测试值:C 83.89,H 4.37,N 2.66。
实施例9
化合物9的制备
该化合物9的制备方法与实施例8的区别仅在于,将实施例8的步骤(5)中的反应物1用等摩尔量的反应物3替换,其他原料、反应步骤以及反应条件与实施例8相同,最后得到化合物9(收率73%)。
MALDI-TOF:m/z:计算值:C70H42N6O2S2:1062.28,实测值:1062.47。
化合物元素分析结果:计算值:C70H42N6O2S2(%):C 79.07,H 3.98,N 7.90;测试值:C 79.06,H 3.97,N 7.92。
运用密度泛函理论(DFT),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E S1和三线态能级ET1。
表1化合物1至化合物9的性能参数
由表1可以看出,本发明的化合物具有较高的三线态能级,当其作为发光层中的主体材料使用时,可以将其三线态激子有效地转移到客体,并防止能量从客体倒流到主体。另外,本发明的化合物还具有较合适的HOMO/LUMO能级,可与相邻层进行能级的匹配,也能覆盖客体的能级。
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有机薄膜层;所述有机薄膜层包括发光层,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2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(HATCN)、聚(3,4-乙烯二氧噻吩)-聚苯乙烯磺酸(PEDOT:PSS)、聚乙烯咔唑(PVK)、三氧化钼(MoO3);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)、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)、9-苯基-3,9-联咔唑(CCP)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、空穴传输层4、电子阻挡层5、发光层6、空穴阻挡层7、电子传输层8、电子注入层9、阴极10。
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膜层,在有机薄膜层上形成阴极。有机薄膜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。
应用例1
本实施例提供一种有机发光器件(OLED器件),具体制备步骤如下:
1)将带有氧化铟锡(ITO)阳极2(厚度为100nm)的玻璃基板1切成50mm×50mm×0.7mm的大小,分别在异丙醇和去离子水中超声处理30分钟,然后暴露在臭氧下约10分钟来进行清洁,将清洗后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化合物a作为空穴注入层3,厚度为10nm;
3)在空穴注入层3上真空蒸镀化合物b作为空穴传输层4,厚度为40nm;
4)在空穴传输层4上真空蒸镀化合物c作为电子阻挡层5,厚度为10nm;
5)在电子阻挡层5上真空共同蒸镀本发明化合物1和掺杂材料化合物d,掺杂比例为3%(质量比),厚度为20nm,作为发光层6;
6)在发光层6上真空蒸镀化合物e作为空穴阻挡层7,厚度为10nm;
7)在空穴阻挡层7上真空蒸镀化合物f与化合物g,掺杂质量比1:1;厚度为30nm,作为电子传输层8;
8)在电子传输层8上真空蒸镀化合物h:LiF,厚度为5nm,作为电子注入层9
9)在电子注入层9上真空蒸镀铝电极,厚度为100nm,作为阴极10。
OLED器件的制备过程中使用的化合物的结构如下:
应用例2
本应用例与应用例1的区别在于,将步骤5)中的化合物1等量替换为化合物2,其他制备步骤均相同。
应用例3
本应用例与应用例1的区别在于,将步骤5)中的化合物1等量替换为化合物3,其他制备步骤均相同。
应用例4
本应用例与应用例1的区别在于,将步骤5)中的化合物1等量替换为化合物4,其他制备步骤均相同。
应用例5
本应用例与应用例1的区别在于,将步骤5)中的化合物1等量替换为化合物5,其他制备步骤均相同。
应用例6
本应用例与应用例1的区别在于,将步骤5)中的化合物1等量替换为化合物6,其他制备步骤均相同。
应用例7
本应用例与应用例1的区别在于,将步骤5)中的化合物1等量替换为化合物7,其他制备步骤均相同。
应用例8
本应用例与应用例1的区别在于,将步骤5)中的化合物1等量替换为化合物8,其他制备步骤均相同。
应用例9
本应用例与应用例1的区别在于,将步骤5)中的化合物1等量替换为化合物9,其他制备步骤均相同。
对比例1
本对比例与应用例1的区别在于,将步骤5)中的化合物1等量替换为对比化合物1,其他制备步骤均相同。
OLED器件性能的测试
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流,然后用电流除以发光面积得到OLED器件在不同电压下的电流密度;用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度;根据OLED器件在不同电压下的电流密度和亮度,得到在相同电流密度下(10mA/cm2)的工作电压V及电流效率CE(cd/A);通过测量OLED器件的亮度达到初始亮度的95%时的时间而获得寿命LT95(在50mA/cm2测试条件下);测试数据如表2所示。
从表2可以看出,本发明提供的OLED器件具有较低的驱动电压、较高的发光效率以及较长的器件寿命,其中工作电压≤3.9V,电流效率CE≥18.2cd/A,寿命LT95≥73h。其中,相对于对比例1,采用本发明化合物的OLED器件的工作电压降低,效率及寿命均提升,这可能得益于本发明的化合物具有合适的HOMO能级,与相邻层更为匹配,更高的三线态能级(≥2.90eV),可以有效地将能量转移到客体并防止其从客体倒流到主体,有效提高OLED器件效率。同时本发明化合物含有螺环的结构有效降低了分子的堆叠,降低分子的结晶性,保证其具有优异的热稳定性和薄膜稳定性,在OLED器件工作时更为稳定,从而提高了OLED器件的寿命。特别地,采用本发明化合物3、化合物7、化合物9的OLED器件均有较高的器件寿命,这可能是因为除了分子间C-H…N作用,还有分子内的C-H…N作用,使得整个分子更为稳定,化学键不易断裂,有利于器件寿命的提升。
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,20表示手机显示面板,30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 (14)
1.一种化合物,所述化合物具有化学式1所示的化学结构:
其中,在化学式1中,X选自氧原子、硫原子、-C(RaRb)-、-N(Ra)-、-PO(Ph)-、-PS(Ph)-、-SO2-、-Si(RaRb)-,或者X与相邻的碳原子形成单键;Ra和Rb各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基、取代或未取代的C1-C20烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C1-C20烷硫基、取代或未取代的C3-C20环烷基;
X1-X8各自独立地选自碳原子或氮原子;
L1和L2各自独立地选自共价单键、取代或未取代的C6-C30亚芳基,取代或未取代的C3-C30亚杂芳基;
R1和R2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C1-C20烷氧基、取代或未取代的C1-C20烷硫基、取代或未取代的C3-C20环状烷基、取代或未取代的C6-C40芳基、取代或未取代的C3-C40杂芳基;n1和n2各自独立地选自0、1、2、3。
10.一种显示面板,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9任一项所述的化合物中的一种或多种。
11.一种显示面板,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,其中发光层包括主体材料和客体材料,其特征在于,所述发光层的客体材料为权利要求1至9任一项所述的化合物中的一种或多种。
12.一种显示面板,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和电子传输层,其中,所述电子传输层的材料为权利要求1至9任一项所述的化合物中的一种或多种。
13.根据权利要求11至12任一项所述的显示面板,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。
14.一种显示装置,包括权利要求11至13任一项所述的显示面板。
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