CN110305110B - 一种化合物、oled显示面板以及电子设备 - Google Patents
一种化合物、oled显示面板以及电子设备 Download PDFInfo
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- 239000000243 solution Substances 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- HITRWHKLCHWBNZ-UHFFFAOYSA-N triphenyl-[4-(9-phenylfluoren-9-yl)phenyl]silane Chemical compound C1=CC=CC=C1C1(C=2C=CC(=CC=2)[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HITRWHKLCHWBNZ-UHFFFAOYSA-N 0.000 description 1
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
本发明提供了一种化合物、OLED显示面板以及电子设备,所述化合物具有式(I)结构;所述OLED显示面板包括第一电极、第二电极以及设置于所述第一电极和第二电极之间的有机薄膜层,所述有机薄膜层包括电子传输层,所述电子传输层包括所述化合物中的任意一种或至少两种的组合;所述电子设备包括所述OLED显示面板;电致发光材料的三线态能级ET≥2.7eV,HOMO能级≤‑5.85eV,玻璃化转换温度>120℃,可以用于OLED显示面板中,提高发光效率,使包括其的电子设备具有更优异的性能。
Description
技术领域
本发明涉及OLED显示面板技术领域,尤其涉及一种化合物、OLED显示面板以及电子设备。
背景技术
随着电发光器件的产品化和实用化,人们希望得到传输效率更高、使用性能更好的电子传输材料,研究人员在这一领域做了一些探索性工作。传统电致发光器件中使用的电子传输材料是三(8-羟基喹啉)铝(Alq3),但Alq3的电子迁移率比较低(大约在l0-6cm2/Vs),使得器件的电子传输与空穴传输不均衡。随着电发光器件产品化和实用化,人们希望得到传输效率更高、使用性能更好的ETL材料,在这一领域,研究人员做了大量的探索性工作。
市场上现有较多使用的电子传输材料像红菲略啉(batho-phenanthroline,BPhen)、浴铜灵(bathocuproine,BCP)和TmPyPB,大体上能符合有机电致发光面板的市场需求,但它们的玻璃化转变温度较低,一般小于85℃,器件运行时,产生的焦耳热会导致分子的降解和分子结构的改变,使面板效率较低和热稳定性较差。同时,这种分子结构对称化很规则,长时间后很容易结晶。一旦电子传输材料结晶,分子间的电荷跃迀机制跟正常运作的非晶态薄膜机制就会产生差异,导致电子传输的性能降低,使得整个器件的电子和空穴迀移率失衡,激子形成效率大大降低,并且激子形成会集中在电子传输层与发光层的界面处,导致器件效率和寿命严重下降。
因此,开发一种具有较高的三线态能级、较高电子迁移率、优异的热稳定性以及薄膜稳定性的电子传输材料非常有必要。
发明内容
针对现有技术的不足,本发明的目的之一在于提供一种化合物,所述化合物具有式(I)结构:
式(I)中,R1、R2、R3、R4均各自独立地选自取代或未取代的C6-C40芳香环、取代或未取代的C5-C40芳香杂环中的任意一种;
式(I)中,X1、X2、X3、X4、X5、X6、X7、X8、X9均各自独立地选自碳原子或氮原子,且X1、X2、X3、X4、X5、X6、X7、X8、X9中至少有一个为氮原子;
式(I)中,Lm均各自独立地选自取代或未取代的C6-C40亚芳基、取代或未取代的C5-C40亚杂芳基中的任意一种;
式(I)中,n选自0或1,m为1;
式(I)中,Ai均各自独立地选自取代或未取代的咔唑基及其衍生物基团、取代或未取代的联咔唑基及其衍生物基团、取代或未取代的芳胺基及其衍生物基团、取代或未取代的吖啶基及其衍生物基团、取代或未取代的吩噻嗪基及其衍生物基团、取代或未取代的吩噁嗪基及其衍生物基团、取代或未取代的吩嗪基及其衍生物基团中的任意一种;
式(I)中,j为1-3的整数,i为1-j的整数;
所述取代的取代基为C1~C10的烷基或环烷基、C2~C10烯基、C1~C6的烷氧基或硫代烷氧基、C6~C30的单环芳烃或稠环芳烃基团、C3~C30的单环杂芳烃或稠环杂芳烃基团中的任意一种。
本发明的目的之二在于提供一种OLED显示面板,所述OLED显示面板包括第一电极、第二电极以及设置于所述第一电极和第二电极之间的有机薄膜层;所述有机薄膜层包括电子传输层;所述电子传输层的材料包括目的之一所述的化合物中的任意一种或至少两种的组合。
本发明的目的之三在于提供一种电子设备,所述电子设备包括目的之二所述的OLED显示面板。
与现有技术相比,本发明具有如下有益效果:
本发明提供的化合物以含氮芳香杂环为母环,并配合供电子基团使用,使得到的电子传输材料具有合适的HOMO和较低的LUMO值,可以提高电子传输的能力,有效阻挡空穴;具有较高的电子迁移率,保证电子能够在发光层中复合,使得激子的产生速率提高;具有较高的玻璃化温度和热分解温度,避免器件在工作时产生的焦耳热对器件寿命和效率的影响;具有优异的薄膜稳定性和均匀性,避免光散射或结晶诱导产生的降解或衰减;具有较高的还原电位,便于电子的传输;使其三线态能级ET≥2.7eV,HOMO能级≤-5.85eV,玻璃化转换温度>120℃。当用于电子传输材料,制备的OLED显示面板具有较低的驱动电压,以及较高的发光效率和使用寿命,其中驱动电压<3.70V,发光效率>120Cd/A,使用寿命>70h;此外该结构具有双极性,使化合物具有较小的激发态偶极矩,当用于发光主体材料时,又够有效降低效率滚降,提升发光亮度和发光效率,工作电压<3.70V,电流效率>70cd/A,寿命>70h;该化合物在应用于OLED显示面板时,能够降低OLED显示面板的阈值电压,并提高其发光效率,延长使用寿命,具有重要的实际应用价值。
附图说明
图1是本发明的一个具体实施方式中提供的OLED显示面板的示意图;
图2是本发明的一个具体实施方式中提供的电子设备的示意图。
具体实施方式
为便于理解本发明,本发明列举实施例如下。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明的目的之一在于提供一种化合物,所述化合物具有式(I)结构:
式(I)中,R1、R2、R3、R4均各自独立地选自取代或未取代的C6-C40芳香环、取代或未取代的C5-C40芳香杂环中的任意一种;
式(I)中,X1、X2、X3、X4、X5、X6、X7、X8、X9均各自独立地选自碳原子或氮原子,且X1、X2、X3、X4、X5、X6、X7、X8、X9中至少有一个为氮原子;
式(I)中,Lm均各自独立地选自取代或未取代的C6-C40亚芳基、取代或未取代的C5-C40亚杂芳基中的任意一种;
式(I)中,n选自0或1,m为1;
式(I)中,Ai均各自独立地选自取代或未取代的咔唑基及其衍生物基团、取代或未取代的芳胺基及其衍生物基团、取代或未取代的吖啶基及其衍生物基团中的任意一种;
式(I)中,j为1-3的整数,例如1、2、3,i为1-j的整数;
所述取代的取代基为C1~C10的烷基或环烷基、C2~C10烯基、C1~C6的烷氧基或硫代烷氧基、C6~C30的单环芳烃或稠环芳烃基团、C3~C30的单环杂芳烃或稠环杂芳烃基团中的任意一种。
所述C1~C10可以是C1、C2、C3、C4、C5、C6、C7、C8、C9、C10等。
所述C2~C10可以是C2、C3、C4、C5、C6、C7、C8、C9、C10等。
所述C1~C6可以是C1、C2、C3、C4、C5、C6等。
所述C6~C30可以是C6、C8、C10、C12、C14、C16、C18、C20、C22、C24、C26、C28、C30等。
所述C3~C30可以是C3、C4、C6、C8、C10、C12、C14、C16、C18、C20、C22、C24、C26、C28、C30等。
式(I)中采用Ai和Lm的方式来表示取代基,意义在于,Ai和Lm代表基团的选择范围,而并非代表一个具体的基团,如当Ai的个数大于等于两个时,取代基Ai可以相同也可以不同,示例性的,当母体基团上取代有两个Ai基团时,即j为2,i为1~2的整数,当两个Ai中的i均为1时,即母核基团上取代有两个D1基团,意味着这两个基团是相同,当着两个Ai中的i分别为1和2时,即母核基团上取代有一个A1和一个为A2,这时候的两个Ai基团则可以是相同的,也可以是不同的。
本发明提供的化合物以含氮芳香杂环为母环,并配合特定种类的供电子基使用,使得到的化合物具有合适的HOMO和较低的LUMO值,可以提高电子传输的能力,有效阻挡空穴;并具有较高的电子迁移率,保证电子能够在发光层中复合,使得激子的产生速率提高;具有较高的玻璃化温度和热分解温度,避免器件在工作时产生的焦耳热对器件寿命和效率的影响;具有优异的薄膜稳定性和均匀性,避免光散射或结晶诱导产生的降解或衰减;具有较高的还原电位,便于电子的传输;使其三线态能级ET≥2.7eV,HOMO能级≤-5.8eV,玻璃化转换温度>120℃;且具有双极性,使化合物具有较小的激发态偶极矩,当用于发光主体材料时,又够有效降低效率滚降,提升发光亮度和发光效率;其该化合物在用于OLED面板的电子传输材料时,可以有效提升器件的电子迁移能力,从而确保器件具有较高的发光效率,较久的使用寿命以及较低的阈值电压。
在一个实施方式中,所述X1、X2、X3、X7、X8、X9中至少有一个为氮原子。
本发明中,X1、X2、X3、X7、X8、X9中至少有一个为氮原子,N原子使得掺杂的基团具有相应的受电子能力,确保材料的LUMO能级与相邻层匹配。
在一个实施方式中,所述X1、X2、X3、X4、X5、X6、X7、X8、X9中有2-6个(例如2、3、4、5、6)为氮原子。
本发明中,X1、X2、X3、X4、X5、X6、X7、X8、X9中有2-6个为氮原子,能够有效调节分子的LUMO能级,从而提高化合物的电子传输能力,并能有效阻挡空穴。
在一个实施方式中,所述Lm均各自独立地选自如下基团中的任意一种:
其中,Zr、Zx、Za、Zb、Zy、Zu、Zo、Zv均各自独立地选自氢原子、取代或未取代的C6-C30芳基、取代或未取代的C6-C30杂芳基、取代或未取代的C6-C30稠芳基、取代或未取代的C6-C30稠杂芳基、取代或未取代的C1-C16亚烷基、取代或未取代的C1-C16亚烷氧基;
p为0-4的整数,r为1-p的整数;
q为0-6的整数,x为1-q的整数;
s、t均各自独立地选自0-3的整数,a为1-t的整数,b为1-s的整数;
g为0-2的整数,y为1-g的整数;
c为0-5的整数,u为1-c的整数;
d为0-3的整数,o为1-d的整数;
e为0-2的整数,v为1-e的整数;
所述取代的取代基为C1~C10的烷基或环烷基、C2~C10烯基、C1~C6的烷氧基或硫代烷氧基、C6~C30的单环芳烃或稠环芳烃基团、C3~C30的单环杂芳烃或稠环杂芳烃基团中的任意一种;
其中,虚线表示连接位点。
在本发明中,Lm优选上述结构,是因为上述结构简单,能够避免过于复杂的基团的引入,增加了分子电化学环境中的不稳定因素,影响器件的使用寿命,并可以最大程度的提升分子结构的溶解度和三线态能级,且分子量较大的化合物不易蒸镀,因此,在不影响化合物发光性能的前提下,尽量设计为结构简单的化合物。
在一个实施方式中,所述Lm均各自独立地选自如下基团中的任意一种:
其中,虚线表示连接位点。
在本发明中,Lm进一步优选上述结构,是因为上述结构简单,一方面避免过于复杂的基团的引入,从而影响器件的使用寿命,并能较大程度的提升分子的溶解度和三线态能级,另一方面避免分子量较大的化合物不易蒸镀的问题,从而提高器件的发光效率和寿命。
在一个实施方式中,所述Ai均各自独立地选自取代或未取代的咔唑基及其衍生物基团,所述取代或未取代的咔唑基及其衍生物基团选自如下基团中的任意一种:
其中,Y选自碳原子、氮原子、氧原子、硫原子或硅原子中的任意一种;
所述r和s均各自独立地选自0-4的整数,所述g为1-r的整数,所述h为1-s的整数;
所述t选自0~3的整数,所述w为1~t的整数;
所述p选自0-2的整数,所述v为1-p的整数;
所述a为0~5的整数,所述d为1~a的整数;
Rg、Rh、Rv、Rw均各自独立地选自氢原子、C1-C20烷基、C1-C20烷氧基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C12-C40咔唑基及其衍生物基团、取代或未取代的C12-C40二苯胺基及其衍生物基团、取代或未取代的C12-C40吖啶基及其衍生物基团中的任意一种;
所述Rd均各自独立地选自取代或未取代的C1~C20亚烷基、取代或未取代的C1~C20亚烷氧基、取代或未取代的C6~C30亚芳基、取代或未取代的C3~C30亚杂芳基中的任意一种;
所述取代的取代基为C1~C10的烷基或环烷基、C2~C10烯基、C1~C6的烷氧基或硫代烷氧基、C6~C30的单环芳烃或稠环芳烃基团、C3~C30的单环杂芳烃或稠环杂芳烃基团中的任意一种;
虚线表示连接位点。
本发明中,Ai优选取代或未取代的咔唑基及其衍生物基团,其具有相对较弱的供电子基,HOMO能级下移,可以有效阻挡空穴越过发光层,提升空穴和电子的复合效率,拓宽发光区域,从而提升器件的寿命。
在一个实施方式中,所述取代或未取代的咔唑基及其衍生物基团选自如下基团中的任意一种:
其中,R选自C1-C20烷基、C1-C20烷氧基、C2-C20烯基、C2-C20炔基、C4-C8环烷基、C6-C40芳香基或C4-C40杂芳基中的任意一种;
虚线表示连接位点。
本发明中,取代或未取代的咔唑基及其衍生物基团进一步优选上述结构,分子之间的空间位阻较大,分子本身的扭曲性较大,增大分子的溶解度,且弱的供电基相连,可以有效调节分子的供受电子能力,从而匹配不同的材料体系。
在一个实施方式中,所述Ai均各自独立地选自取代或未取代的吖啶基及其衍生物基团,所述取代或未取代的吖啶基及其衍生物基团选自如下基团中的任意一种:
其中,所述Y和Z均各自独立地选自碳原子、氮原子、氧原子、硫原子和硅原子中的任意一种;
所述r、s均各自独立地选自0~4的整数,所述g为1~r的整数,所述h为1~s的整数;
所述p、q均各自独立地选自0~2的整数,所述v为1~p的整数,所述k为1~q的整数;
所述a为0~5的整数,所述d为1~a的整数;
所述Rg、Rh、Rv和Rk均各自独立地选自氢原子、C1~C20烷基、C1~C20烷氧基、取代或未取代的C6~C40芳基、取代或未取代的C4~C40杂芳基、取代或未取代的C12~C40咔唑基及其衍生物基团、取代或未取代的C12~C40二苯胺基及其衍生物基团、取代或未取代的C12~C40吖啶基及其衍生物基团、取代或未取代的C3~C40吖嗪基及其衍生物基团中的任意一种或至少两种的组合;
所述Rd均各自独立地选自取代或未取代的C1~C20亚烷基、取代或未取代的C1~C20亚烷氧基、取代或未取代的C6~C30亚芳基、取代或未取代的C3~C30亚杂芳基中的任意一种;
所述取代的取代基为C1~C10的烷基或环烷基、C2~C10烯基、C1~C6的烷氧基或硫代烷氧基、C6~C30的单环芳烃或稠环芳烃基团、C3~C30的单环杂芳烃或稠环杂芳烃基团中的任意一种;
虚线表示连接位点。
本发明中,Ai优选为取代或未取代的吖啶基及其衍生物基团,由于吖啶基团本身强的供电子能力,使得分子的HOMO能级上移,匹配合适的母核,可以作为主体材料使用;分子容易合成,鉴于吖啶中N原子的sp3杂化,分子的溶解度较好;当吖啶基衍生物基团中Y为N时,吩嗪结构具有较强的供电子能力,而化合物的母环结构具有较强的受电子能力,使得化合物的带隙减少,三线态减少,适合作为主体材料,优选作为红光主体材料;当吖啶基衍生物基团中Y为O/S时,相比吩嗪具有相对较弱的供电子能力,带隙相对较大,三线态也相对较大,适合作为主体材料,优选作为红光主体材料和绿光主体材料。
在一个实施方式中,所述取代或未取代的吖啶基及其衍生物基团选自如下基团中的任意一种:
其中,虚线表示连接位点。
本发明中进一步优选取代或未取代的吖啶基及其衍生物基团选自上述结构,避免过多官能团的引入,增加了分子电化学环境中的不稳定因素,影响器件的使用寿命,且化合物具有较好的溶解度,能够提高器件的发光效率和寿命,此外分子量较大的化合物不易蒸镀,因此,在不影响化合物发光效率的前提下,尽量设计为结构简单的化合物。
在一个实施方式中,所述Ai均各自独立地选自取代或未取代的芳胺基及其衍生物基团,所述取代或未取代的芳胺基及其衍生物基团选自如下基团中的任意一种:
其中,所述a和b均各自独立地选自0~5的整数,所述e为1~a的整数,所述f为1~b的整数;
所述Re、Rf均各自独立地选自氢原子、C1-C20烷基、C1-C20烷氧基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40杂芳基、取代或未取代的C12-C40咔唑基及其衍生物基团、取代或未取代的C12-C40二苯胺基及其衍生物基团、取代或未取代的C12-C40吖啶基及其衍生物基团、取代或未取代的C3-C40吖嗪基及其衍生物基团中的任意一种;
所述取代的取代基为C1~C10的烷基或环烷基、C2~C10烯基、C1~C6的烷氧基或硫代烷氧基、C6~C30的单环芳烃或稠环芳烃基团、C3~C30的单环杂芳烃或稠环杂芳烃基团中的任意一种;
虚线表示连接位点。
本发明中Ai优选取代或未取代的芳胺基及其衍生物基团,是因为芳胺类基团的供电子能力介于咔唑衍生物和吖啶衍生物之间,可以有效的调节分子的HOMO能级,适合不同材料体系,与相邻层更好的匹配;且芳胺及其衍生物基团比较稳定,构成的分子热稳定性较好,具有较高的三线态能级,适合做主体材料,优选做红光和绿光主体材料,符合量产线对热稳定性的要求。
在一个实施方式中,所述取代或未取代的芳胺及其衍生物基团选自如下基团中的任意一种:
其中,虚线表示连接位点。
本发明中进一步优选取代或未取代的芳胺基及其衍生物基团选自上述结构,避免过多官能团的引入,增加了分子电化学环境中的不稳定因素,影响器件的使用寿命,且具有较好的溶解度,此外分子量较大的化合物不易蒸镀,因此,在不影响化合物发光效率的前提下,尽量设计为结构简单的化合物。
在一个实施方式中,所述R1和R4相同,且R2和R3相同。
本发明中,优选R1和R4相同,且R2和R3相同,这样化合物的分子对称性好,合成简便,且能保证化合物的受电子基团的受电子能力的均一性。
在一个实施方式中,所述j为1。
本发明中j为1,既能保证分子具有较高的玻璃化温度又利于分子的热稳定性,从而进一步提升了器件的寿命的稳定性;同时避免了蒸镀时因分子量过大,蒸镀温度过高而导致的热分解的风险,避免了器件制作过程中不必要的麻烦。
在一个实施方式中,所述化合物包括如下HB01-HB48结构的化合物中的任意一种:
木发明的目的之二在于提供一种OLED显示面板,所述OLED显示面板包括第一电极、第二电极以及设置于所述第一电极和第二电极之间的有机薄膜层;所述有机薄膜层包括电子传输层;所述电子传输层的材料包括目的之一所述的化合物中的任意一种或至少两种的组合。
在一个实施方式中,所述有机薄膜层还包括电子注入层,所述电子注入层包括目的之一所述的化合物中的任意一种或至少两种的组合。
在一个实施方式中,所述有机薄膜层还包括发光层,所述发光层的主体材料为包括目的之一所述的化合物中的任意一种或至少两种的组合。
在一个实施方式中,所述OLED显示面板,还包括空穴传输层、空穴注入层、电子阻挡层和空穴阻挡层中的任意一种或至少两种的组合。
在本发明提供的OLED显示面板中,第一电极(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。第一电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)等第一电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,第一电极材料还可以选自除以上列举的第一电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第一电极的材料。
在本发明提供的OLED显示面板中,第二电极(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。第二电极材料也可以选自多层金属材料例如LiF/Al、LiO2/Al、BaF2/Al等。除了以上列举的第二电极材料以外,第二电极材料还可以是有助于电子注入的材料及其组合,包括已知的适合做第二电极的材料。
OLED显示面板的基底可以是刚性基板,例如硼硅酸盐玻璃、浮法钠钙玻璃、高折射率玻璃、不锈钢等,也可以是柔性基板,例如聚酰亚胺(PI)塑料衬底、聚对苯二甲酸乙二酯(PET)塑料衬底、聚萘二甲酸乙二醇酯(PEN)塑料衬底、聚醚砜树脂衬底(PES)、聚碳酸酯塑料衬底(PC)、超薄柔性玻璃衬底、金属箔片衬底等。
在本发明提供的OLED显示面板中,空穴注入材料、空穴传输材料及电子阻挡材料均各自独立地选自N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺、4,4',4″-三(咔唑-9-基)三苯胺、1,3-二咔唑-9-基苯、4,4'-二(9-咔唑)联苯、3,3'-二(N-咔唑基)-1,1'-联苯、2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺、N,N'-二(萘-2-基)-N,N'-二(苯基)联苯-4,4'-二胺、聚(3,4-乙烯二氧噻吩)-聚苯乙烯磺酸、聚乙烯咔唑、9-苯基-3,9-联咔唑、三氧化钼中的任意1种或至少2种的组合。
在本发明提供的OLED显示面板中,发光材料包括主体材料和客体材料。其中,主体材料选自2,8-二(二苯基氧膦基)二苯并噻吩(PPT)、4,4'-二(9-咔唑)联苯(CBP)、2,8-双(二苯基膦氧基)二苯并呋喃(PPF)、双(4-(9H-咔唑基-9-基)苯基)二苯硅烷(SiCz)、二(2-二苯氧化膦基)二苯醚(DPEPO)、1,3-双[3,5-二(吡啶-3-基)苯基]苯(BMPYPHB)、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶(B3PYMPM)、9-(3-(9H-咔唑基-9-基)苯基)-9H-咔唑-3-氰基(mCPCN)、9-苯基-9-[4-(三苯基硅烷基)苯基]-9H-芴(TPSi-F)、聚乙烯基咔唑(PVK)和聚芴(PFO)中的任意一种或一种以上,或目的之一提供的化合物中的任意一种或至少两种的组合。客体材料选自荧光材料、磷光发光材料或热活化延迟荧光材料。荧光材料例如可以选自BczVBi、香豆素-6、DCJTB等,磷光发光材料例如可以选自Ir配合物、Pt配合物、Cu配合物、Os配合物等。
在本发明提供的OLED显示面板中,空穴阻挡材料选自2,8-二(二苯基氧膦基)二苯并噻吩、TSPO1、TPBi、2,8-双(二苯基膦氧基)二苯并呋喃、二(2-二苯氧化膦基)二苯醚、氟化锂、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶、4,7-二苯基-1,10-菲啰啉、1,3,5-三[(3-吡啶基)-3-苯基]苯、三[2,4,6-三甲基-3-(3-吡啶基)苯基]硼烷、1,3-双(3,5-二吡啶-3-基苯基)苯、1,3-双[3,5-二(吡啶-3-基)苯基]苯、2,4,6-三(联苯基-3-基)-1,3,5-三嗪、二苯基二[4-(吡啶-3-基)苯基]硅烷、碳酸铯、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝、8-羟基喹啉-锂、三(8-羟基喹啉)铝中的任意1种或至少2种的组合。
在本发明实施例中,OLED显示面板的制作过程为:在透明或不透明的光滑的基板上形成阳极(第一电极),在阳极上形成有机薄层,在有机薄层上形成阴极(第二电极)。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。
本发明的目的之三在于提供一种电子设备,所述电子设备包括目的之二所述的OLED显示面板。
在一个实施方式中,所述电子设备可以是手机、电脑、液晶电视、智能手表、智能汽车、VR或AR头盔等。
本发明提供了若干个示例性的式(1)结构的化合物的制备方法。在随后的制备例中,对化合物的合成进行示例性的描述。
制备例1
化合物HB03的制备
制备方法如下:
(1)化合物HB03-1的制备:
在250mL圆底烧瓶中,2,6-二溴-4-碘-吡啶(10mmol)、2,4-二苯-6-硼酸酯基-嘧啶(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物HB03-1。
(2)化合物HB03的制备:
在250mL圆底烧瓶中,将中间产物HB03-1、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和9H-咔唑(25mmol)加入到干燥的1,4-二氧六环(150mL)中,在氮气氛围下回流48小时,得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物HB03。
化合物HB03元素分析结构(分子式C49H32N6):理论值:C,83.50;H,4.58;N,11.92。测试值:C,83.50;H,4.59;N,11.91。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:704.27,测试值:704.82。
制备例2
化合物HB11的制备
制备方法如下:
(1)化合物HB11-1的制备:
在250mL圆底烧瓶中,2,6-二溴-4-碘-苯(10mmol)、2,6-二萘基-4-硼酸酯基-吡啶(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物HB11-1。
(2)化合物HB11的制备:
在250mL圆底烧瓶中,将中间产物HB11-1、碘化铜(15mmol)、叔丁醇钾(65mmol)、1,2-二氨基环己烷(12mmol)和9H-咔唑(25mmol)加入到干燥的1,4-二氧六环(150mL)中,在氮气氛围下回流48小时,得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间产物HB11。
化合物HB11元素分析结构(分子式C68H43N3):理论值:C,90.54;H,4.80;N,4.66。测试值:C,90.55;H,4.79;N,4.66。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:901.35,测试值:902.09。
制备例3
化合物HB35的制备
备方法如下:
(1)化合物HB35-1的制备:
在250mL圆底烧瓶中,2,6-二溴-4-碘-苯(10mmol)、2,6-二苯基-4-硼酸酯基-吡啶(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物HB35-1。
(2)化合物HB35的制备:
在250mL圆底烧瓶中,将中间产物HB35-1(10mmol)、2-(4-硼酸酯基)苯-咔唑(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物HB35。
化合物HB35元素分析结构(分子式C64H43N3):理论值:C,90.01;H,5.07;N,4.92。测试值:C,90.02;H,5.06;N,4.92。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:853.35,测试值:854.05。
制备例4
化合物HB44的制备
制备方法如下:
(1)化合物HB44-1的制备:
在250mL圆底烧瓶中,2,6-二溴-4-碘-苯(10mmol)、2,4-二苯基-6-硼酸酯基-嘧啶(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物HB44-1。
(2)化合物HB44的制备:
在250mL圆底烧瓶中,将中间产物HB44-1(10mmol)、10-(4-硼酸酯基)苯-吩噁嗪(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物HB44。
化合物HB35元素分析结构(分子式C56H37N5O):理论值:C,84.51;H,4.69;N,8.80;O,2.01。测试值:C,84.52;H,4.68;N,8.80;O,2.01。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:795.30,测试值:795.93。
制备例5
化合物HB31的制备
(1)化合物HB31-1的制备:
在250mL圆底烧瓶中,2,6-二溴-4-碘代吡啶(10mmol)、2,4-二苯基-6-硼酸酯基-嘧啶(22mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物HB31-1。
(2)化合物HB31的制备:
在250mL圆底烧瓶中,将中间产物HB31-1(10mmol)、(4-硼酸酯基苯)-二苯胺(12mmol)和Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/乙醇(20mL)和碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到最终产物HB31。
化合物HB31元素分析结构(分子式C55H38N6):理论值:C,84.37;H,4.89;N,10.73。测试值:C,84.37;H,4.88;N,10.74。通过液相质谱联用分析得ESI-MS(m/z)(M+):理论值:782.32,测试值:782.93。
将制备例1-5制备得到的化合物进行化合物的模拟计算:
有机材料的单线态和三线态的能级差可以通过Guassian 09软件(Guassian Inc.完成,能级差ΔEst具体的模拟方法参照J.Chem.Theory Comput.,2013,DOI:10.1021/ct400415r,分子结构优化和激发均可用TD-DFT方法“B3LYP”和基组“6-31g(d)”完成,Tg采用差示扫描量热法测量,本案针对制备例1-8制备的化合物以及对比例选用的化合物C1和C2,结果如表1所示。
表1
由表1可以看出,本发明实施例中所有化合物的三线态能级均大于2.8eV,玻璃化转换温度均大于127℃左右。同时,本案实施例材料的三线态能级大于2.8eV,可以有效的利用在蓝光中,阻止激子的回传,使激子限制在发光区,利于扩宽发光区域,提升器件发光效率和寿命。
下文中,本发明将通过如下实施例进行详细解释以便更好的理解本发明的各个方面及其优点。然而,应当理解,以下的实施例是非限制性的而且仅用于说明本发明的某些实施方案。
实施例1
本实施例提供一种OLED显示面板,如图1所示,OLED显示面板包括: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、电子注入层9和阴极10(铝电极),其中ITO阳极2的厚度是10nm,空穴注入层3的厚度是5nm,第一空穴传输层4的厚度是50nm、第二空穴传输层5的厚度是10nm、发光层6的厚度是20nm、第一电子传输层7的厚度是5nm、第二电子传输层8的厚度是20nm、电子注入层9的厚度是1nm,铝电极10的厚度是15nm,其中图中箭头表示出光方向。
OLED显示面板的制备步骤如下:
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;将所得的具有ITO阳极2的玻璃基板安装到真空沉积设备上;
2)在真空度为2×10-6Pa下,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,厚度为5nm,该层作为空穴注入层3;
3)在空穴注入层3上真空蒸镀第一空穴传输层2材料为N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPD),厚度为50nm,作为第一空穴传输层4;
4)在第一空穴传输层4上真空蒸镀第二空穴传输层5材料为1,3-二咔唑-9-基苯(mCP),厚度为10nm,作为第二空穴传输层5;
5)第二空穴传输层5上共沉积发光层6,发光层6的主体材料为CBP,客体材料为Ir(pyy)3,化合物CBP与Ir(ppy)3的质量比为97:3,厚度为20nm;
6)在发光层6上真空蒸镀第一电子传输层7,第一电子传输层7的材料为制备例1制备得到的HB03,厚度为5nm;
7)在第一电子传输层7上真空蒸镀第二电子传输层8,第二电子传输层8的材料为BPen,厚度为20nm;
8)在第二电子传输层8真空蒸镀电子注入层9,电子注入层9的材料为LiF,厚度为1nm;
9)在电子注入层9上真空蒸镀铝电极,厚度为15nm,作为阴极10。
实施例2
与实施例1的区别在于,将HB03替换为HB11。
实施例3
与实施例1的区别在于,将HB03替换为HB35。
实施例4
与实施例1的区别在于,将HB03替换为HB44。
实施例5
与实施例1的区别在于,将HB03替换为HB31。
对比例1
与实施例1的区别在于,将HB03替换为C1。
OLED显示面板性能测试:
本案涉及到表1中的制备例1-5制备的化合物以及对比例选用的化合物C1作为电子传输层材料,分别做成OLED显示面板,采用Spectroscan PR 705光谱仪和Keithley 236电流电压源测量系统检测器件的效率、电压,电压和效率均是在电流密度为10mA/cm2测得的,LT95的寿命测试如下:使用亮度计在10000cd/m2亮度下,保持恒定的电流,测量有机电致发光器件的亮度降为9500cd/m2的时间,单位为小时结果如表2所示。
表2
由表2可知,本发明提供的OLED显示面板具有较低的驱动电压,以及较高的发光效率和使用寿命,其中驱动电压小于3.70V,发光效率大于120Cd/A,使用寿命大于70h。相对于对比例1,显示面板的以上性能均具有明显的提升,这主要得益于本发明的材料具有较浅的LUMO值,与相邻发光层的能级更匹配;具有更高的三线态能级,可以有效阻挡激子的回流和空穴越过发光层。
实施例6
本实施例提供一种OLED显示面板,如图1所示,OLED显示面板包括: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、电子注入层9和阴极10(铝电极),其中ITO阳极2的厚度是10nm,空穴注入层3的厚度是5nm,第一空穴传输层4的厚度是50nm、第二空穴传输层5的厚度是10nm、发光层6的厚度是20nm、第一电子传输层7的厚度是5nm、第二电子传输层8的厚度是20nm、电子注入层9的厚度是1nm,铝电极10的厚度是15nm。
OLED显示面板的制备步骤如下:
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;将所得的具有ITO阳极2的玻璃基板安装到真空沉积设备上;
2)在真空度为2×10-6Pa下,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,厚度为5nm,该层作为空穴注入层3;
3)在空穴注入层3上真空蒸镀第一空穴传输层2材料为N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPD),厚度为50nm,作为第一空穴传输层4;
4)在第一空穴传输层4上真空蒸镀第二空穴传输层5材料为1,3-二咔唑-9-基苯(mCP),厚度为10nm,作为第二空穴传输层5;
5)第二空穴传输层5上共沉积发光层6,发光层6的主体材料为制备例1制备得到的HB03,客体材料为FIrpic,化合物HB03与FIrpic的质量比为97:3,厚度为20nm;
6)在发光层6上真空蒸镀第一电子传输层7,第一电子传输层7的材料为BPen,厚度为5nm;
7)在第一电子传输层7上真空蒸镀第二电子传输层8,第二电子传输层8的材料为Alq3,厚度为20nm;
8)在第二电子传输层8真空蒸镀电子注入层9,电子注入层9的材料为LiF,厚度为1nm;
9)在电子注入层9上真空蒸镀铝电极,厚度为15nm,作为阴极10。
实施例7
与实施例6的区别在于,将HB03替换为HB11。
实施例8
与实施例6的区别在于,将HB03替换为HB35。
实施例9
与实施例6的区别在于,将HB03替换为HB44。
实施例10
与实施例6的区别在于,将HB03替换为HB31。
对比例2
与实施例6的区别在于,将HB03替换为C1。
将制备例1-5制备的化合物以及对比例选用的化合物C1作为发光层的主体材料分别做成OLED显示面板,对其进行性能测试,具体测试方法与上述相同,测试结果见表3:
表3
由表3可知,相对于对比例2,本发明提供的OLED显示面板具有更小的工作电压,工作电压<3.70V,提升3%左右;更高的电流效率,大于70cd/A以上,提升10%左右;更长的器件寿命,寿命>70h,提升11%以上。显示面板的以上性能均具有明显的提升,这主要得益于本发明的材料具有高的三线态能级,可以有效的将能量从主体材料传递到客体发光材料,防止激子回传,拓宽发光区域,有效的提升激子的利用率,提升光致发光效率。
本发明实施例的又一方面提供了一种电子设备,包括上文所述的OLED显示面板,其中电子设备可以为触摸显示屏、手机、平板计算机、笔记本电脑、电纸书、电视机、VR或AR头盔或智能手表等任何具有显示功能的电子设备。图2为本发明实施例提供的一种电子设备的示意图。其中,1为手机显示屏。
申请人声明,本发明通过上述实施例来说明本发明的详细工艺设备和工艺流程,但本发明并不局限于上述详细工艺设备和工艺流程,即不意味着本发明必须依赖上述详细工艺设备和工艺流程才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (8)
1.一种化合物,其特征在于,所述化合物具有式(I)结构:
式(I)中,R1、R2、R3、R4均各自独立地选自取代或未取代的C6芳香环、取代或未取代的C5芳香杂环中的任意一种;
式(I)中,X1、X2、X3、X4、X5、X6、X7、X8、X9均各自独立地选自碳原子或氮原子,且X1、X2、X3、X4、X5、X6、X7、X8、X9中有2-6个为氮原子,X4、X5、X6均为碳原子;
式(I)中,Lm选自如下基团中的任意一种:
式(I)中,n选自0或1;
Rg、Rh、Rv、Rw各自独立地选自氢原子、C1~C20烷基、C1~C20烷氧基、取代或未取代的C6芳基、取代或未取代的C12二苯胺基;
Rd选自取代或未取代的C6亚芳基;
Re、Rf均各自独立地选自氢原子、C1-C20烷基、C1-C20烷氧基、取代或未取代的C12二苯胺基;
r、s各自独立地选自0~4的整数;
t选自0~3的整数;
p为0~2的整数;
a和b各自独立地选自0~5的整数;
式(I)中,j为1;
所述取代的取代基为C1~C10的烷基或环烷基、C1~C6的烷氧基或硫代烷氧基、C6~C14的单环芳烃或稠环芳烃基团中的任意一种。
4.根据权利要求1所述的化合物,其特征在于,所述R1和R4相同,且R2和R3相同。
6.一种OLED显示面板,其特征在于,所述OLED显示面板包括第一电极、第二电极以及设置于所述第一电极和第二电极之间的有机薄膜层;
所述有机薄膜层包括电子传输层;
所述电子传输层的材料包括权利要求1-5任一项所述的化合物中的任意一种或至少两种的组合。
7.根据权利要求6所述的OLED显示面板,其特征在于,所述有机薄膜层还包括发光层,所述发光层的主体材料为1-5任一项所述的化合物中的任意一种或至少两种的组合。
8.一种电子设备,其特征在于,所述电子设备包括权利要求6或7所述的OLED显示面板。
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