CN112479987B - 一种芴类磷光化合物及其制备方法和有机电致发光器件 - Google Patents

一种芴类磷光化合物及其制备方法和有机电致发光器件 Download PDF

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CN112479987B
CN112479987B CN202011527964.3A CN202011527964A CN112479987B CN 112479987 B CN112479987 B CN 112479987B CN 202011527964 A CN202011527964 A CN 202011527964A CN 112479987 B CN112479987 B CN 112479987B
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王永光
汪康
张鹤
王进政
黄悦
张雪
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明公开了一种芴类磷光化合物及其制备方法和有机电致发光器件，属于化学及有机发光材料技术领域，该磷光化合物的结构通式为：
Figure DDA0002851385430000011
式中，L1、L2各自独立地为连接键、经取代或未经取代的C6‑C30芳基、经取代或未经取代的C6‑C30杂芳基中的至少一种。含该磷光化合物的有机电致发光器件的驱动电压较低，寿命和效率较高。本发明提供的磷光化合物，通过选择特定的杂环的配体结合，调节化合物的波长，使得其在用于有机电致发光器件后，可以提高器件的发光效率和使用寿命。

Description

一种芴类磷光化合物及其制备方法和有机电致发光器件
技术领域
本发明涉及化学及有机发光材料技术领域，具体是一种芴类磷光化合物及其制备方法和有机电致发光器件。
背景技术
OLED是空穴和电子双注入型发光器件，将电能直接转化为有机半导体材料分子的光能。相比传统的CRT、LCD、PDP等显示器件，OLED兼顾了已有显示器的所有优点，同时具有自己独特的优势，既有高亮度、高对比度、高清晰度、宽视角、宽色域等来实现高品质图像，又具备超薄、超轻、低驱动电压、低功耗、宽温度等特性来满足便携式设备的轻便、省电、始于户外操作的需求；而自发光、发光效率高、响应时间短、透明、柔性等更是OLED显示独具的特点。
贵金属配合物作为磷光材料，充分利用了单线态和三线态激子，相对荧光材料只利用单线态激子，比例高达75％的三线态激子的有效利用，使得基于磷光材料的PhOLED实现了100％的内量子效率。近三年来，磷光材料逐渐取代传统的荧光材料，成为OLED发光材料的研究热点。但是由于磷光材料合成工艺比较复杂，耗时久，寿命低，所以磷光材料的进一步开发迫在眉睫。
发明内容
本发明实施例的目的在于提供一种芴类磷光化合物，以解决上述背景技术中提出的问题。
为实现上述目的，本发明实施例提供如下技术方案：
一种芴类磷光化合物，其结构通式为式I：
Figure BDA0002851385420000021
式中，m为0或1，n为0或1，且m、n不能同时为0；
R1、R2各自独立地为经取代或未经取代的C1-C30烷基、经取代或未经取代的C2-C30烯基、经取代或未经取代的C2-C30炔基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的3到7元杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的3到30元杂芳基、与相邻取代基连接形成经取代或未经取代的单环或多环的C3-C30脂肪族环或芳香族环中的至少一种；
L1、L2各自独立地为连接键、经取代或未经取代的C6-C30芳基、经取代或未经取代的C6-C30杂芳基中的至少一种；
Ar1、Ar2、Ar3、Ar4各自独立地为C1-C60烷基、C6-C60芳基、C3-C60杂芳基、C3-C60环烷基、C1-C60烷基氨基、C6-C60芳基氨基、C6-C60芳氧基、包含一个或多个选自N、O和S的杂原子的5-6元杂环烷基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基、C6-C60芳基甲硅烷基、三(C6-C60)芳基甲硅烷基、金刚烷基、C7-C60环烷基、C2-C60烯基、C2-C60炔基、C1-C60烷基羰基、C1-C60芳基羰基中的至少一种。
优选的，与相邻取代基连接形成经取代或未经取代的单环或多环的C3-C30脂肪族环或芳香族环中的碳原子置换成至少一个选自氮、氧和硫的杂原子。
优选的，Ar1、Ar2、Ar3、Ar4各自独立地为未经取代或经至少一个取代基取代的烷基、未经取代或经至少一个取代基取代的烯基、未经取代或经至少一个取代基取代的炔基、未经取代或经至少一个取代基取代的环烷基、未经取代或经至少一个取代基取代的杂环烷基、未经取代或经至少一个取代基取代的芳基、未经取代或经至少一个取代基取代的杂芳基、未经取代或经至少一个取代基取代的芳基甲硅烷基、未经取代或经至少一个取代基取代的烷基甲硅烷基、未经取代或经至少一个取代基取代的烷基氨基、未经取代或经至少一个取代基取代的芳基氨基中的至少一种。
优选的，所述取代基独立地为氘、卤素、氰基、羧基、硝基、羟基、C1-C60烷基、C6-C60芳基、C3-C60杂芳基、C3-C60环烷基、C1-C60烷氧基、C1-C60烷基氨基、C6-C60芳基氨基、C6-C60芳氧基、C6-C60芳硫基、包含一个或多个选自N、O和S的杂原子的5-6元杂环烷基、三(C1-C60)烷基甲硅烷基、二(C1-C60)烷基、(C6-C60)芳基甲硅烷基、三(C6-C60)芳基甲硅烷基、金刚烷基、C7-C60二环烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基羰基、C1-C60烷基羰基、C1-C60芳基羰基中的至少一种。
优选的，所述磷光化合物的化学结构式为式1～式114中的任一种：
Figure BDA0002851385420000031
Figure BDA0002851385420000041
Figure BDA0002851385420000051
Figure BDA0002851385420000061
Figure BDA0002851385420000071
Figure BDA0002851385420000081
Figure BDA0002851385420000091
Figure BDA0002851385420000101
需要说明的是，在上述技术方案中，术语“经取代或未经取代的”意指被选自以下的一个、两个或更多个取代基取代：氘；卤素基团；腈基；羟基；羰基；酯基；甲硅烷基；硼基；经取代或未经取代的烷基；经取代或未经取代的环烷基；经取代或未经取代的烷氧基；经取代或未经取代的烯基；经取代或未经取代的烷基胺基；经取代或未经取代的杂环基胺基；经取代或未经取代的芳基胺基；经取代或未经取代的芳基；和经取代或未经取代的杂环基，或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代，或者不具有取代基。例如，“两个或更多个取代基相连接的取代基”可以包括联苯基。换言之，联苯基可以为芳基，或者可以解释为两个苯基相连接的取代基。
本发明实施例的另一目的在于提供一种上述的芴类磷光化合物的制备方法，其包括以下步骤：
在保护气氛下，将反应物A、反应物B、Pd(pph3)4、碳酸钾置于溶剂中进行反应，并经提纯，得到中间体C；
在保护气氛下，将中间体C溶解于无水四氢呋喃(THF)中，并加入MgBr Me进行反应后，再滴加氯化铵溶液进行分液，提纯，得到中间体D；
将中间体D加入到四氢呋喃(THF)中，并加入甲磺酸(MSA)、多聚磷酸和乙醇进行反应后，再经提纯，得到中间体E；
将中间体E加入到二氯甲烷中后，再加入N-氯代丁二酰亚胺(NCS)进行反应，并经提纯，得到中间体F；
在保护气氛下，将Pd(pph3)4、碳酸钾、反应物H、反应物I和中间体F置于溶剂中进行反应，得到所述的磷光化合物；
其中，反应物A的结构式为式A，反应物B的结构式为式B，中间体C的结构式为式C，中间体D的结构式为式D，中间体E的结构式为式E，中间体F的结构式为式F，反应物H的结构式为式H，反应物I的结构式为式I：
Figure BDA0002851385420000121
优选的，所述溶剂为甲苯、乙醇和水的混合液。
具体的，上述制备方法的合成路线如下：
Figure BDA0002851385420000122
其具体包括以下步骤：
1)中间体C的制备：将反应物A和反应物B加入反应容器中之后，再加入Pd(pph3)4、碳酸钾，以及溶剂甲苯、乙醇和水的混合液，用氮气充分置换空气三次；升温至85-95℃，反应约16-20小时。反应完毕后降温分液，旋干甲苯层，得深色固体，用二氯溶解过硅胶柱，二氯甲烷：石油醚＝1：(3.5-4.5)冲出大部分产品，旋干得白色固体中间体C。
2)中间体D的制备：将产品C溶解到无水THF中，氮气保护，0℃搅拌20-40分钟。再加入化合物MgBrMe，反应1-3小时后，逐渐升温到室温并反应10-14小时。向反应液中滴加饱合的氯化铵溶液，分液，THF萃取一次水层，合并有机层并用无水硫酸镁干燥5-15分钟，旋干得到体中间体D所示的化合物。
3)中间体E的制备：将中间体D加入到THF中，0℃下冷却20-40分钟，再分别加入MSA(20-40mL)、多聚磷酸和乙醇。反应2-4小时后升到室温搅拌12-16小时，有固体析出，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体E。
4)中间体F的制备：将中间体E加入到二氯甲烷中，室温下搅拌20-40分钟，再缓慢加入NCS。反应14-18小时后结束，旋干有机层得到淡黄色固体，再加入石油醚、适量乙醇和水搅拌过夜，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体F。
5)磷光化合物的制备：将Pd(pph3)4、碳酸钾、原料H、I和中间体F加入到反应瓶中，再加入甲苯、乙醇和水的混合液，氮气保护，升温到80-100℃反应22-26小时。降温，抽滤，得深色滤液，旋干滤液，得到固体，加二氯甲烷溶解，过硅胶漏斗，得到化学式I所示的磷光化合物。
上述制备方法中，化学式I的合成，优选的溶剂是甲苯、乙醇和水体积比在2：0.5-1：0.5-1之间，所选用的催化剂和碱分别为Pd(pph3)4和碳酸钾，摩尔比在1：100-300之间，用量不超过主反应物的5％(mol)，且反应温度不超过100℃，反应时间不超过24小时。最终产物是根据反应试剂的大致摩尔比(基于组成)确定的。
本发明实施例的另一目的在于提供一种上述磷光化合物在制备有机电致发光器件中的应用。
本发明实施例的另一目的在于提供一种有机电致发光器件，包括阳极、阴极以及至少一层设置在所述阳极和所述阴极之间的有机物层，所述的有机物层包含上述的磷光化合物。
优选的，所述有机物层包括发光层；所述发光层包括主体材料和掺杂材料；所述主体材料部分或全部包含所述的磷光化合物。
所述阳极的种类没有特殊限制，为本领域技术人员熟知的常规阳极即可，更优选为ITO(氧化铟锡)、氧化锡、氧化锌、氧化铟中的一种。所述阳极的厚度优选为
Figure BDA0002851385420000141
所述阴极的种类没有特殊限制，为本领域技术人员熟知的常规阴极即可，更优选为Al、Li、Na、K、Mg、Ca、Au、Ag、Pb中的一种。所述阴极的厚度优选为
Figure BDA0002851385420000142
优选的，所述有机物层包括发光层；所述发光层包括主体材料和掺杂材料；所述掺杂材料部分或全部包含所述的磷光化合物。
所述掺杂材料优选为Ir(ppy)3等铱金属配合物。
此外，有机物层还可以包括其它功能层，其它功能层具体可选自以下功能层中的一种或几种：空穴注入层(HIL)、空穴传输层(HTL)、空穴注入-空穴传输功能层(即兼具空穴注入及空穴传输功能)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)、电子传输-电子注入功能层(即兼具电子传输及电子注入功能)。
上述各个功能层的种类没有特殊限制，为本领域技术人员熟知的常规功能层即可。优选的：所述空穴注入层为2-TNATA(即N1-(2-萘基)-N4,N4-二(4-(2-萘基(苯基)氨基)苯基)-N1-苯基苯-1,4-二胺)、酞菁和卟啉化合物、星爆三芳基胺、导电聚合物、n型半导电有机络合物、金属有机络合物中的一种；所述空穴注入层的厚度优选为
Figure BDA0002851385420000151
所述空穴传输层为NPB(即N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺)、TPD(即N,N'-二苯基-N,N'-(3-甲基苯基)-1,1'-联苯-4,4'-二胺)、PAPB(即N,N'-双(菲-9-基)-N,N'-二苯基联苯胺)芳基胺咔唑化合物、吲哚并咔唑化合物中的一种；所述空穴传输层的厚度优选为
Figure BDA0002851385420000152
所述电子传输层为Alq3、香豆素6号、***衍生物、唑衍生物、噁二唑衍生物、咪唑衍生物、芴酮衍生物、蒽酮衍生物中的一种；所述电子传输层的厚度优选为
Figure BDA0002851385420000153
Figure BDA0002851385420000154
所述电子注入层为LiF、CsF、Li2O、Al2O3、MgO中的一种；所述电子注入层的厚度优选为0.1～10nm。
在本发明实施例中，可通过溶液涂覆法和真空沉积法的方式形成上述各种功能层。溶液涂覆法意指旋涂、浸涂、喷墨印刷、丝网印刷、喷洒法等，但不限于此。
另外，上述的有机电致发光器件可以同样原理应用在有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)或有机薄膜晶体管(OTF T)等上，但不限于此。
与现有技术相比，本发明实施例的有益效果是：
本发明实施例提供的一种芴类磷光化合物，通过选择特定的杂环的配体结合，调节化合物的波长，使得其在用于有机电致发光器件后，可以提高器件的发光效率和使用寿命。另外，本发明实施例提供的芴类磷光化合物的制备方法，原料易得，合成过程简单，产品产率较高。
具体实施方式
以下是本发明的实施举例，下面实施例是为了帮助本发明理解而提供的，并不是将本发明的内容限定在这个范围。并且本发明的各实施例中具体没有列举化合物的制备方法是有关行业通常应用的方法，实施例中记载的方法，在制备其他化合物时，也可以参考。
实施例1
该实施例提供了一种芴类磷光化合物，其制备方法如下：
Figure BDA0002851385420000161
1)中间体C1的制备：反应物A-1(73.5mmo)l和B1-1(80.85mmol)加入反应容器中之后，再加入Pd(pph3)4(7.35mmol)、碳酸钾(14.7mmol)，以及溶剂甲苯、乙醇和水的混合液600mL，用氮气充分置换空气三次；升温至90℃，反应约18小时。反应完毕后降温分液，旋干甲苯层，得深色固体，用二氯甲烷约30mL溶解，然后过硅胶柱，二氯甲烷：石油醚＝1：4冲出大部分产品，旋干得白色固体产品C1-1(61.7mmol)。
2)中间体D1-1的制备：将产品C1-1(61.7mmol)溶解到无水400mL THF中，氮气保护，0℃搅拌30分钟。再加入化合物MgBrMe约185.1mmol，反应2小时后，逐渐升温到室温并反应12小时。向反应液中滴加饱合的氯化铵溶液，分液，THF萃取一次水层，合并有机层并用无水硫酸镁干燥10分钟，旋干得到体中间体D1-1所示的化合物约55mmol。
3)中间体E1-1的制备：将中间体D1-1(55mmol)加入到THF(200mL)中，0℃下冷却30分钟，再分别加入MSA(60mL)、52g多聚磷酸和100mL乙醇。反应3小时后升到室温搅拌14小时，有固体析出，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体E1-1。
4)中间体F1-1的制备：将中间体E1-1(55mmol)加入到二氯甲烷中，室温下搅拌30分钟，再缓慢加入NCS(60mmol)。反应16小时后结束，旋干有机层得到淡黄色固体，再加入石油醚、适量乙醇和水搅拌过夜，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体F1-1。
5)芴类磷光化合物1的制备：将Pd(pph3)4(0.5mmol)、碳酸钾(100mmol)、原料H1-1(60mmol)和中间体F1-1(50mmol)加入到反应瓶中，再加入甲苯、乙醇和水的混合液300mL，氮气保护，升温到90℃反应24小时。降温，抽滤，得淡黄色滤液，旋干滤液，得到固体，加二氯甲烷溶解，过硅胶漏斗，得到芴类磷光化合物1(18.6g，91％)。
该芴类磷光化合物的HPLC纯度:大于99.9％。质谱:理论值为420.56；测试值为420.13。
实施例2
该实施例提供了一种芴类磷光化合物，其制备方法如下：
Figure BDA0002851385420000171
1)中间体C1-1的制备：反应物A-1(73.5mmo)l和B1-1(80.85mmol)加入反应容器中之后，再加入Pd(pph3)4(7.35mmol)、碳酸钾(14.7mmol)，以及溶剂甲苯、乙醇和水的混合液600mL，用氮气充分置换空气三次；升温至90℃，反应约18小时。反应完毕后降温分液，旋干甲苯层，得深色固体，用二氯甲烷约30mL溶解，然后过硅胶柱，二氯甲烷：石油醚＝1：4冲出大部分产品，旋干得白色固体产品C1-1(61.7mmol)。
2)中间体D1-1的制备：将产品C1-1(61.7mmol)溶解到无水400mL THF中，氮气保护，0℃搅拌30分钟。再加入化合物MgBrMe约185.1mmol，反应2小时后，逐渐升温到室温并反应12小时。向反应液中滴加饱合的氯化铵溶液，分液，THF萃取一次水层，合并有机层并用无水硫酸镁干燥10分钟，旋干得到体中间体D1-1所示的化合物约55mmol。
3)中间体E1-1的制备：将中间体D1-1(55mmol)加入到THF(200mL)中，0℃下冷却30分钟，再分别加入MSA(60mL)、52g多聚磷酸和100mL乙醇。反应3小时后升到室温搅拌14小时，有固体析出，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体E1-1。
4)中间体F1-1的制备：将中间体E1-1(55mmol)加入到二氯甲烷中，室温下搅拌30分钟，再缓慢加入NCS(60mmol)。反应16小时后结束，旋干有机层得到淡黄色固体，再加入石油醚、适量乙醇和水搅拌过夜，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体F1-1。
5)芴类磷光化合物10的制备：将Pd(pph3)4(0.5mmol)、碳酸钾(100mmol)、原料H1-10(60mmol)和中间体F1-1(50mmol)加入到反应瓶中，再加入甲苯、乙醇和水的混合液300mL，氮气保护，升温到90℃反应24小时。降温，抽滤，得淡黄色滤液，旋干滤液，得到固体，加二氯甲烷溶解，过硅胶漏斗，得到芴类磷光化合物10(20.8g，产率84％)。
该芴类磷光化合物的HPLC纯度:大于99.9％。质谱:理论值为456.77；测试值为456.67。
实施例3
该实施例提供了一种芴类磷光化合物，其制备方法如下：
Figure BDA0002851385420000191
1)中间体C1-62的制备：反应物A-62(73.5mmo)l和B1-62(80.85mmol)加入反应容器中之后，再加入Pd(pph3)4(7.35mmol)、碳酸钾(14.7mmol)，以及溶剂甲苯、乙醇和水的混合液600mL，用氮气充分置换空气三次；升温至90℃，反应约18小时。反应完毕后降温分液，旋干甲苯层，得深色固体，用二氯甲烷约30mL溶解，然后过硅胶柱，二氯甲烷：石油醚＝1：4冲出大部分产品，旋干得白色固体产品C1-62(61.7mmol)。
2)中间体D1-62的制备：将产品C1-62(61.7mmol)溶解到无水400mL THF中，氮气保护，0℃搅拌30分钟。再加入化合物MgBrMe约185.1mmol，反应2小时后，逐渐升温到室温并反应12小时。向反应液中滴加饱合的氯化铵溶液，分液，THF萃取一次水层，合并有机层并用无水硫酸镁干燥10分钟，旋干得到体中间体D1-62所示的化合物约55mmol。
3)中间体E1-62的制备：将中间体D1-62(55mmol)加入到THF(200mL)中，0℃下冷却30分钟，再分别加入MSA(60mL)、52g多聚磷酸和100mL乙醇。反应3小时后升到室温搅拌14小时，有固体析出，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体E1-1。
4)中间体F1-62的制备：将中间体E1-1(55mmol)加入到二氯甲烷中，室温下搅拌30分钟，再缓慢加入NCS(60mmol)。反应16小时后结束，旋干有机层得到淡黄色固体，再加入石油醚、适量乙醇和水搅拌过夜，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体F1-62。
5)芴类磷光化合物62的制备：将Pd(pph3)4(0.5mmol)、碳酸钾(100mmol)、原料H1-10(60mmol)和中间体F1-1(50mmol)加入到反应瓶中，再加入甲苯、乙醇和水的混合液300mL，氮气保护，升温到90℃反应24小时。降温，抽滤，得淡黄色滤液，旋干滤液，得到固体，加二氯甲烷溶解，过硅胶漏斗，得到芴类磷光化合物62(20.8g，产率84％)。
该芴类磷光化合物的HPLC纯度:大于99.9％。质谱:理论值为560.74；测试值为560.18。
实施例4
该实施例提供了一种芴类磷光化合物，其制备方法如下：
Figure BDA0002851385420000201
1)中间体C1-76的制备：反应物A-76(73.5mmo)l和B2-76(80.85mmol)加入反应容器中之后，再加入Pd(pph3)4(7.35mmol)、碳酸钾(14.7mmol)，以及溶剂甲苯、乙醇和水的混合液600mL，用氮气充分置换空气三次；升温至90℃，反应约18小时。反应完毕后降温分液，旋干甲苯层，得深色固体，用二氯甲烷约30mL溶解，然后过硅胶柱，二氯甲烷：石油醚＝1：4冲出大部分产品，旋干得白色固体产品C2-76(61.7mmol)。
2)中间体D2-76的制备：将产品C2-76(61.7mmol)溶解到无水400mL THF中，氮气保护，0℃搅拌30分钟。再加入化合物MgBrMe约185.1mmol，反应2小时后，逐渐升温到室温并反应12小时。向反应液中滴加饱合的氯化铵溶液，分液，THF萃取一次水层，合并有机层并用无水硫酸镁干燥10分钟，旋干得到体中间体D2-76所示的化合物约55mmol。
3)中间体E2-76的制备：将中间体D2-76(55mmol)加入到THF(200mL)中，0℃下冷却30分钟，再分别加入MSA(60mL)、52g多聚磷酸和100mL乙醇。反应3小时后升到室温搅拌14小时，有固体析出，直接抽滤，分别用水、乙醇和石油醚冲洗滤饼，干燥，得到中间体E2-76。
4)芴类磷光化合物76的制备：化合物76的制备：将Pd2(dba)3(0.6mmol)和叔丁醇钠(66mmol)，加入到无水甲苯中，氮气保护，室温搅拌30分钟。再加入中间体D-76(30mmol)和反应物E-76(36mmol)，最后加P(t-bu)3(6mmol)，升温到100℃反应24小时。降温，抽滤，过硅胶漏斗，得到芴类磷光化合物76(13.6g，产率84％)。
该芴类磷光化合物的HPLC纯度:大于99.9％。质谱:计算值为539.72；测试值为539.84。
实施例5
该实施例提供了一种芴类磷光化合物，其制备方法如下：
Figure BDA0002851385420000221
1)中间体F3-103的制备方法与中间体F1-10的相同。
2)芴类磷光化合物102的制备：化合物102的制备：将Pd(pph3)4(0.5mmol)、碳酸钾(100mmol)、原料H3-102(60mmol)和中间体F3-102(50mmol)加入到反应瓶中，再加入甲苯、乙醇和水的混合液300mL，氮气保护，升温到90℃反应24小时。降温，抽滤，得淡黄色滤液，旋干滤液，得到固体，加二氯甲烷溶解，过硅胶漏斗，得到芴类磷光化合物102(20.8g，产率84％)。
该芴类磷光化合物的HPLC纯度:大于99.9％。质谱:计算值为587.77；测试值为587.93。
实施例6～实施例15
因结构通式为发明内容中的化学式I的其他磷光化合物的制备方法的合成路线和原理均与上述所列举的实施例1相同，只需要将原料分别替换为目标产物中的相应配体结构对应的原料，物料用量按照相应化学计量比相应调整即可得到相对应的磷光化合物，所以在此不再穷举，本发明实施例参照实施例1至5的制备方法完成对磷光化合物2，10，15，36，39，42，43，58，62，67的合成，其质谱、分子式、产率如表1所示。
表1
Figure BDA0002851385420000222
Figure BDA0002851385420000231
器件实施例1
该器件实施例提供了一种有机电致发光器件，其具体的制备方法包括以下步骤：
将涂层厚度为
Figure BDA0002851385420000232
的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥，转移到等离子体清洗机里，将上述基板洗涤5分钟，送到蒸镀机里。首先ITO(阳极)上面蒸镀
Figure BDA0002851385420000233
紧接着蒸镀
Figure BDA0002851385420000234
上述芴类磷光化合物1和掺杂物质Ir(ppy)3 95:5重量比混合蒸镀
Figure BDA0002851385420000235
蒸镀电子传输层
Figure BDA0002851385420000236
蒸镀电子注入层
Figure BDA0002851385420000237
蒸镀阴极
Figure BDA0002851385420000238
形式制备得到有机电致发光器件。
器件实施例2～器件实施例14
参照上述器件实施例1提供的制备方法，将器件实施例1中使用的芴类磷光化合物1分别替换为上述实施例提供的芴类磷光化合物2，5，10，15，17，36，39，42，43，58，62，67，76作为主体材料，制备得到相应的有机电致发光器件。
器件对比例1
该器件对比例制造了一种有机电致发光器件。具体的，按照器件实施例1的制备方法，将发光层中的主体材料芴类磷光化合物1替换为化合物CBP，其他方法相同，以制得有机电致发光器件。其中，CBP的结构式如下：
Figure BDA0002851385420000241
对上述得到的器件的性能发光特性测试，测量采用KEITHLEY 2400型源测量单元，CS-2000分光辐射亮度计，以评价驱动电压，发光效率和器件寿命，评价结果如下表2。
表2
Figure BDA0002851385420000242
Figure BDA0002851385420000251
表2中，器件性能测试结果是以器件对比例1作为参照，即将器件对比例1各项性能指标设为1.0，器件实施例的各项性能指标的值为与器件对比例1相比的倍数。由表2的结果可以看出本发明提供的芴类磷光化合物可以应用于有机电致发光器件，并且与含现有主体材料的有机电致发光器件相比，含本发明提供的芴类磷光化合物的有机电致发光器件的电压、效率与寿命均获得改善。
以上述依据本发明的理想实施例为启示，通过上述的说明内容，相关工作人员完全可以在不偏离本项发明技术思想的范围内，进行多样的变更以及修改。本项发明的技术性范围并不局限于说明书上的内容，必须要根据权利要求范围来确定其技术性范围。

Claims (3)

1.一种芴类磷光化合物，其特征在于，所述磷光化合物的化学结构式为式1，2，5，10，15，17，36，39，42，43，58，62，67，76中的任一种：
Figure FDA0003463132960000011
2.一种有机电致发光器件，包括阳极、阴极以及至少一层设置在所述阳极和所述阴极之间的有机物层，其特征在于，所述的有机物层包含如权利要求1所述的磷光化合物。
3.根据权利要求2所述的一种有机电致发光器件，其特征在于，所述有机物层包括发光层；所述发光层包括主体材料和掺杂材料；所述主体材料部分或全部包含所述的磷光化合物。
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