CN107698490B - 一种有机发光化合物及其制备方法和应用 - Google Patents

一种有机发光化合物及其制备方法和应用 Download PDF

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CN107698490B
CN107698490B CN201710784735.1A CN201710784735A CN107698490B CN 107698490 B CN107698490 B CN 107698490B CN 201710784735 A CN201710784735 A CN 201710784735A CN 107698490 B CN107698490 B CN 107698490B
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林文晶
马晓宇
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Olide (Shanghai) Photoelectric Material Technology Co., Ltd.
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Abstract

本发明涉及一种有机发光化合物及其制备方法和应用，涉及有机电致发光器件领域。该有机发光化合物，具有式(I)结构，
Figure DDA0001397740860000011
其中，A选自取代或未取代的C1～C30的烷基、C3～C30的环烷基、C6～C60的芳基或C8～C60的稠环基；Ar选自取代或未取代的C6～C60的芳基或C4～C60的杂环芳基；Ar1、Ar2独立选自取代或未取代的C6～C60的芳基、C4～C60的杂环芳基或C8～C60的稠环基；n为1～5的整数。该有机发光化合物通过选择特定的母核结构以及取代基A、Ar、Ar1和Ar2，使得化合物应用于器件后，其发光效率提高，使用寿命长，实验结果表明，该有机发光化合物应用于OLED，得到的器件与现有空穴传输层材料应用于发光器件，发光效率提高20％以上，使用寿命提高50％以上。该有机发光化合物的制法简单易行，适于工业化生产。

Description

一种有机发光化合物及其制备方法和应用
技术领域
本发明涉及有机电致发光器件领域，具体涉及一种有机发光化合物及其制备方法和应用。
背景技术
一般的有机发光现象是利用有机物电子能量转换成光能量的现象。利用有机发光现象的有机电致器件是一般具有阳极和阴极及之间包含有机层的结构，这里有机层是为了提高有机电致器件的效率和稳定性各自不同物质组成的多层结构形成。比如空穴注入层、空穴传输层、发光层、电子传输层及电子注入层等组成。
有机电致器件里使用在有机层的材料按技能分为发光材料和电子传输材料，比如空穴注入材料、空穴传输材料、电子传输材料、电子注入材料等形式分类。
现在便携式显示屏是面板大小增加的趋势，因而导致基准便携式显示屏要求更高的消费电力。因而，有限的电力供应源的电池在便携式显示屏立场上一个很重要的因素，另外效率和寿命是必须解决的状况。
效率和寿命、驱动电压是互相连贯，一般效率增加启动电压低下，减少启动电压驱动时发生的电阻加热(Joule heating)而引起的有机物结晶，结果出现寿命增加的倾向。但是改善上述有机层不能极大化效率。因为，各有机层之间能级及T1值，物质的固有特性(移动度，界面特性等)等最佳组合时才能达到长寿命和高效率目的。
基准的空穴传输层为了降低驱动电压开发空穴移动度(hole mobility)快的物质，为了提高空穴移动度开发了组装密度(packing density)高HOMO价跟发光层HOMO价接近的物质，但空穴移动度快物质一般显现效率减少的倾向。
一般有机电致器件空穴移动度比电子移动度(electron mobility)快，因而出现电子不均衡(charge unbalance)现象最终出现发光效率及寿命减少现象。
使用组装密度(packing density)低的物质减少空穴移动度，因而调节发光层内的电子均衡情况会出现低的组装密度(packing density)提高驱动电压，驱动电压提高增加电子加热而减少器件寿命情况发生，因此迫切要求组装密度(packing density)高同时空穴俘获能力优秀的物质的开发。
发明内容
本发明的目的是提供一种新型结构的有机发光化合物及其制备方法和应用，本发明所述的有机发光化合物作为空穴传输层材料应用于有机电致发光器件，使得得到的器件不仅发光效率高，而且使用寿命长。
为了实现上述目的，本发明的技术方案具体如下：
本发明提供了一种有机发光化合物，具有式(I)结构，
Figure BDA0001397740850000021
其中，所述A选自取代或未取代的C1～C30的烷基、C3～C30的环烷基、C6～C60的芳基或C8～C60的稠环基；
所述Ar选自取代或未取代的C6～C60的芳基或C4～C60的杂环芳基；
所述Ar1、Ar2各自独立的选自取代或未取代的C6～C60的芳基、C4～C60的杂环芳基或C8～C60的稠环基；
n为1～5的整数。
优选的，所述Ar选自取代的C6～C15的芳基或C4～C15的杂环芳基。
再优选的，所述Ar选自苯、联苯或三联苯。
优选的，所述A选自取代或未取代的C5～C15的烷基、C6～C30的环烷基、C12～C30的芳基或C13～C40的稠环基。
再优选的，所述A选自甲基、乙基、2-氟-乙基、2-氰基-丙基、异丙基、叔丁基、戊烷基、庚烷基、十二烷基、式(a-1)、式(a-2)、式(a-3)、式(a-4)、式(a-5)、式(a-6)、式(a-7)、式(a-8)、式(a-9)、式(a-10)、式(a-11)、式(a-12)、式(a-13)、式(a-14)、式(a-15)、式(a-16)、式(a-17)、式(a-18)、式(a-19)、式(a-20)、式(a-21)、式(a-22)或式(a-23)；
式(a-1)-式(a-23)的结构式如下：
Figure BDA0001397740850000031
Figure BDA0001397740850000041
优选的，所述Ar1或Ar2选自取代或未取代的C12～C30的芳基、C12～C30的杂环芳基或C12～C30的稠环基。
再优选的，所述Ar1或Ar2为苯基、萘基、联苯基、N-苯基-9H—咔唑基和式(b-1)～式(b-20)中的任意一种：
Figure BDA0001397740850000042
Figure BDA0001397740850000051
优选n为1或2。
优选的，所述有机发光化合物为式1～式51中的任意一种：
Figure BDA0001397740850000052
Figure BDA0001397740850000061
Figure BDA0001397740850000071
Figure BDA0001397740850000081
Figure BDA0001397740850000091
Figure BDA0001397740850000101
本发明还提供了一种本发明所述的有机发光化合物的制备方法，包括以下步骤：
将式(II)结构的化合物、含A取代基的溴化物和式(III)结构的化合物混合反应，得到式(I)结构的有机发光化合物：
Figure BDA0001397740850000111
其中，所述A选自取代或未取代的C1～C30的烷基、C3～C30的环烷基、C6～C60的芳基或C8～C60的稠环基；
所述Ar选自取代或未取代的C6～C60的芳基或C4～C60的杂环芳基；
所述Ar1、Ar2各自独立的选自取代或未取代的C6～C60的芳基、C4～C60的杂环芳基或C8～C60的稠环基；
n为1～5的整数。
本发明还提供了一种本发明所述的有机发光化合物的制备方法，具体包括以下步骤：
氮气条件下，将反应容器里加入含A取代基的溴化物和四氢呋喃，低温-78℃滴加n-丁基锂，加完后继续在-78℃搅拌30min，常温搅拌3h，然后在低温-78℃条件下，滴加溶解在四氢呋喃式(II)所示的苯并蒽酮，滴加以后常温搅拌16小时后停止反应，加入氯化铵水溶液，加入乙酸乙酯萃取有机物，有机层用无水MgSO4干燥后，减压蒸馏去掉有机溶剂，过硅胶柱提纯化合物得到S；
氮气条件下，在反应容器里加S，式(III)所示的化合物及二氯甲烷，在反应体系里，滴加溶解在二氯甲烷的三氟化硼乙醚，常温搅拌2h停止反应，加入甲醇和蒸馏水，用二氯甲烷萃取有机物，有机层用MgSO4干燥，减压蒸馏去掉溶剂，过硅胶柱提纯得到式(I)所示的有机发光化合物；合成路线如下：
Figure BDA0001397740850000121
本发明还提供了一种本发明所述的有机发光化合物作为空穴传输层材料在制备有机电致发光器件中的应用。
本发明的有益效果是：
与现有技术相比，本发明提供了一种新型结构的有机发光化合物通过选择特定的母核结构以及取代基A、Ar、Ar1和Ar2，使得得到的化合物应用于有机电致发光器件后器件的发光效率提高，而且使用寿命长，实验结果表明，本发明提供的有机发光化合物应用于OLED，得到的器件与现有的空穴传输层材料应用于发光器件，其发光效率提高20％以上，使用寿命提高50％以上。该有机发光化合物的制法简单易行，适于工业化生产。
具体实施方式
实施例1化合物的合成
P1的合成
Figure BDA0001397740850000131
氮气条件下，将反应容器里加入1-溴二苯并呋喃(44g，178mmol)和四氢呋喃500mL，低温-78℃慢慢滴加n-丁基锂71mL(2.5M，178mmol)，加完后继续在-78℃搅拌30min，常温搅拌3h，然后在低温-78℃条件下，滴加溶解在四氢呋喃500mL的苯并蒽酮(41g，178mmol)，滴加以后常温搅拌16小时后停止反应，加入氯化铵水溶液，加入乙酸乙酯萃取有机物，有机层用无水MgSO4干燥后，减压蒸馏去掉有机溶剂，过硅胶柱提纯化合物得到S1(42.4g，60％)。
氮气条件下，在反应容器里加S1(11.4g，28.7mmol)，三苯胺(7.4g，30.1mmol)及二氯甲烷(MC)570mL，在反应体系里，慢慢滴加溶解在二氯甲烷(120mL)的三氟化硼乙醚(3.8mL，30.1mmol)，常温搅拌2h停止反应，加入甲醇和蒸馏水，用二氯甲烷萃取有机物，有机层用MgSO4干燥，减压蒸馏去掉溶剂，过硅胶柱提纯得到化合物P1(15.3g，85％)。
P10的合成
Figure BDA0001397740850000141
氮气条件下，将反应容器里加2-溴-9，9-二甲基芴(24.3g，89mmol)和四氢呋喃300mL，低温-78℃慢慢滴加n-丁基锂35.5mL(2.5M，89mmol)，加完后继续在-78℃搅拌30min，常温搅拌3h，然后在低温-78℃条件下，滴加溶解在四氢呋喃300mL的苯并蒽酮(20.5g，89mmol)，滴加以后常温搅拌16小时，停止反应后，加入氯化铵水溶液，加入乙酸乙酯萃取有机物，有机层用MgSO4干燥后，减压蒸馏去掉有机溶剂，用硅胶柱提纯化合物得到S10(26.4g，70％)。
氮气条件下，在反应容器里加S10(12.2g，28.7mmol)，N-([1，1'-联苯]-4-基)-N-苯基-[1，1'-联苯]-4-胺(11.97g，30.1mmol)及四氢呋喃450mL，在反应体系里，慢慢滴加溶解在150mL二氯甲烷的三氟化硼乙醚(3.8mL，30.1mmol)，常温搅拌2h停止反应，加入甲醇和蒸馏水，用二氯甲烷萃取有机物，有机层用MgSO4干燥，减压蒸馏去掉溶剂，过硅胶柱提纯得到化合物P10(17.3g，75％)。
P13的合成
Figure BDA0001397740850000151
氮气条件下，在反应容器里加入2-溴二苯并[b，d]噻吩(14g，89mmol)及四氢呋喃350mL，低温-78℃条件下，慢慢滴加n-丁基锂35.5mL(2.5M，89mmol)，-78℃搅拌30min，常温搅拌3h，然后在低温-78℃条件下，滴加溶解在四氢呋喃300mL的苯并蒽酮(20.4g，89mmol)，滴加以后常温搅拌16小时，停止反应后，加入NH4Cl水溶液，用乙酸乙酯萃取有机物，有机层用MgSO4干燥后，减压蒸馏去掉有机溶剂，用硅胶柱提纯化合物得到S13(29.5g，80％)。
氮气条件下，加S13(35.7g，86.1mmol)，4-溴三苯胺(84g，259mmol)及二氯甲烷(MC)600mL，慢慢滴加阿托恩试剂(Eaton's reagent)3mL，常温搅拌2h后，停止反应，加入乙醇和蒸馏水，用二氯甲烷萃取有机物，有机层用MgSO4干燥，减压蒸馏去掉溶剂以后，过硅胶柱提纯得到化合物S13-1(48.4g，78％)。
氮气条件下，在反应容器里加入S13-1(12.2g，16.9mmol)、2-萘硼酸(3.2g，18.4mmol)、四三苯基膦钯(0.7g，1.08mmol)、碳酸钾(5.3g，38.3mmol)，甲苯60mL，乙醇20mL及蒸馏水20mL，120℃条件下搅拌3h，反应结束后停止反应，加入蒸馏水和乙酸乙酯萃取，有机层用MgSO4干燥，减压蒸馏去掉溶剂后，过硅胶柱提纯得到化合物P13(8.4g，65％)。
P20的合成
Figure BDA0001397740850000161
氮气条件下，反应容器里加入溴苯(38.2g，96.12mmol)及四氢呋喃500mL，低温-78℃条件下，慢慢滴加n-丁基锂38.34mL(2.5M，96.12mmol)，加入-78℃搅拌30min，常温搅拌3h以后重新低温-78℃条件下滴加溶解在四氢呋喃300mL的苯并蒽酮(22.1g，96.12mmol)，滴加以后常温搅拌16小时，用氯化铵水溶液停止反应，用乙酸乙酯萃取有机物，有机层用MgSO4干燥后减压蒸馏去掉有机溶剂，用硅胶柱提纯化合物得到S20(17.8g，60％)。
反应容器里氮气条件下加S20(8.9g，28.7mmol)，4-溴-N，N-二苯基胺(28g，86.1mmol)及二氯甲烷(MC)570mL。向体系里慢慢滴加溶解在120mL二氯甲烷的三氟化硼乙醚(3.8mL，30.1mmol)，常温搅拌2h停止反应，加入甲醇和蒸馏水，用二氯甲烷萃取有机物，有机层用硫酸镁干燥，减压蒸馏去掉溶剂以后，过硅胶柱提纯得到化合物S20-1(13.8g，78％)。
将反应物S20-1(10.4g，16.9mmol)，二苯并[b，d]噻吩-4-基硼酸(4.2g，18.4mmol)，(三苯酰膦)钯(0.7g，1.08mmol)，碳酸钾(5.3g，38.3mmol)，甲苯60mL，乙醇20mL及蒸馏水后120℃下搅拌3小时，反应结束后，用蒸馏水洗涤，乙酸乙酯萃取有机层，提取有机层用硫酸镁干燥，减压蒸馏去掉溶剂后，用硅胶柱提纯化合物得到化合物P20(7.9g，65％)。
P24的合成
Figure BDA0001397740850000171
氮气条件下，反应容器里加入1-溴-9，9'-螺二芴(52.7g，133.5mmol)及四氢呋喃350mL，低温-78℃条件下，慢慢滴加n-丁基锂53.25mL(2.5M，133.5mmol)，-78℃搅拌30min，常温搅拌3h，然后低温-78℃条件下，滴加溶解在四氢呋喃500mL的苯并蒽酮(30.7g，133.5mmol)，滴加后常温搅拌16小时停止反应，加入NH4Cl水溶液，用乙酸乙酯萃取有机物，有机层用MgSO4干燥后，减压蒸馏去掉有机溶剂，过硅胶柱提纯化合物得到S24(44g，60％)。
氮气条件下，反应容器里加入S24(16.7g，28.7mmol)，二苯胺(12g，30.1mmol)及二氯甲烷(MC)570mL，慢慢滴加溶解在120mL二氯甲烷的三氟化硼乙醚(3.8mL，30.1mmol)，常温搅拌2h停止反应，加入甲醇和蒸馏水，用二氯甲烷萃取有机物，有机层用硫酸镁干燥，减压蒸馏去掉溶剂后，用硅胶柱子提纯得到化合物S24-1(17g，85％)。
反应容器里加S24-1(15.5g，22.1mmol)、9，9-二甲基-2-溴芴(6.7g，24.4mmol)、醋酸钯(0.19g，0.88mmol)、2-二环己基膦-2′，6′-二甲氧基-联苯(S-Phos)(0.91g，2.21mmol)、叔丁醇钠(5.3g，55.4mmol)、甲苯110mL，回流条件下加热1h，反应结束后，蒸馏水洗涤，用二氯甲烷萃取有机物，有机层用MgSO4干燥后减压蒸馏去掉有机溶剂，用硅胶柱子提纯化合物得到P24(15.2g，77％)。
P44的合成
Figure BDA0001397740850000181
氮气条件下，反应容器里加入1-溴-9，9'-螺二芴(52.7g，133.5mmol)及四氢呋喃350mL，低温-78℃条件下，慢慢滴加n-丁基锂53.25mL(2.5M，133.5mmol)，-78℃搅拌30min，常温搅拌3h，然后低温-78℃条件下，滴加溶解在四氢呋喃500mL的苯并蒽酮(30.7g，133.5mmol)，滴加以后常温搅拌16小时停止反应，加入NH4Cl水溶液，用乙酸乙酯萃取有机物，有机层用MgSO4干燥后，减压蒸馏去掉有机溶剂，过硅胶柱提纯化合物得到S44(43.7g，60％)。
氮气条件下，应容器里加入S44(15.7g，28.7mmol)，N-([1，1'-联苯]-4-基)-N-苯基-[1，1'-联苯]-4-胺(12g，30.1mmol)及二氯甲烷570mL，常温搅拌2h停止反应，加入乙醇和蒸馏水，用二氯甲烷萃取有机物，有机层用MgSO4干燥，减压蒸馏去掉溶剂后，用硅胶柱子提纯得到化合物P44(22g，83％)。
P1-P51分别对应式1-式51的化合物，采用与上述所述式(I)化合物的合成方法合成化合物P1～P51中的其它化合物，对得到的P1～P51的化合物的结构进行鉴定，其质谱(FD-MS)值如表1所示。
表1P1～P51化合物的质谱值
Figure BDA0001397740850000191
实施例2有机电致发光器件的制备
将实施例1制备的有机发光化合物作为空穴传输层材料用于制备绿光有机电致发光器件，具体制备方法为：
首先ITO(阳极)上面蒸镀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("2-TNATA")60nm，紧接着蒸镀本发明合成的化合物P1 60nm、主体物质4，4'-N，N'-联苯二咔唑("CBP")和掺杂物质三(2-苯基吡啶)铱("Ir(ppy)3")90:10重量比混合蒸镀30nm、蒸镀空穴阻挡层("BAlq")10nm厚度、蒸镀"Alq3"40nm厚度、蒸镀电子注入层LiF 0.2nm、蒸镀阴极Al为150nm形式制备得到有机电致发光器件。
同样的，将P1换成本发明实施例1所述的其他化合物，用同样的方法制备得到其他有机电致发光器件。
对比例1～3
用与实施例2的同样方法制备有机电致发光器件，将化合物P1替代成比较化合物1、比较化合物2、比较化合物3，得到对应的有机电致发光器件。
Figure BDA0001397740850000201
实施例3
将本发明的实施例1中的化合物P1～化合物P46制备的有机电致发光器件，比较例1-比较例3制备的有机电致发光器件加偏压(bias voltage)，用(photoresearch)公司的PR-650测试电致发光特性(EL)，5000cd/m2基准亮度下，mcscience制备的寿命装备测试T95，测定结果见表2。
表2
Figure BDA0001397740850000211
Figure BDA0001397740850000221
上述表2的结果能确认适用本发明的有机发光材料作为空穴材料的有机发光器件是表现出高的效率及表示长寿命，即本发明的有机发光化合物适用在空穴层时候跟比较化合物1(NPB)比明显提高了效率和寿命。
比较例4
以下述化学式a表示的化合物a用作蓝光主体物质，以下述化学式b表示的化合物b作蓝光掺杂物质，2-TNATA(4,4',4”-三[2-萘基苯基氨基]三苯基胺)用作空穴注入物质，α-NPD(N,N’-二(1-萘基)-N,N'-二苯基联苯二胺)作为空穴传输层，制备了如下结构的有机电致发光器件：ITO/2-TNATA(80nm)/α-NPD(30n m)/化合物a+化合物b(30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)。阳极用了康宁公司的(Corning)15Ω/cm2
Figure BDA0001397740850000223
ITO玻璃基板截成50mm x 50mm x 0.7mm大小，分别在纯的丙酮和异丙醇中超声清洗15分钟后，在UV臭氧中清洗30分钟后使用。上述基板上部真空蒸镀了2-TANATA(厚度为80nm)形成了空穴注入层，在上述空穴注入层上部真空蒸镀了α-NPD(厚度为30nm)形成了空穴传输层，在空穴传输层上部真空蒸镀了以化合物a及化合物b(5％掺杂)(厚度为30nm)形成了发光层，之后，在上述发光层上部真空蒸镀了Alq3化合物(厚度为30nm)形成了电子传输层，在上述电子传输层上部依次真空蒸镀了Lif(厚度为0.5nm)作电子注入层，Al(厚度为60nm)为阴极制备了如同表2中表示的有机电致发光器件，将此作为比较样品1。
Figure BDA0001397740850000222
Figure BDA0001397740850000231
实施例4
将本发明的有机发光化合物作为空穴传输层材料用于制备蓝光有机电致发光器件：
上述比较例1中：将作为发光层中荧光主体的化合物换成上述实施例1-46合成的化合物，与上述比较例1使用了同样的方法，制备了结构如：ITO/2-TN ATA(80nm)/α-NPD(30nm)/[主体化合物1～46+蓝光掺杂化合物b(5％)](30nm)/A lq3(30nm)/LiF(0.5nm)/Al(60nm)的有机电致发光器件。将此表示为样品1～46。
实施例5
评价比较样品1及样品1～46的发光特性。
将本发明的实施例1中的化合物1～化合物46制备的有机电致发光器件，比较例1制备的有机电致发光器件加偏压(bias voltage)，用(photoresearch)公司的PR-650测试电致发光特性(EL)，5000cd/m2基准亮度下，mcscience制备的寿命装备测试T95，测定结果见表3。
表3
Figure BDA0001397740850000232
Figure BDA0001397740850000241
上述表3的结果能确认适用本发明提供的有机发光化合物还可以作为发光层主体材料用于制备蓝光有机电致发光器件，所得器件表现出高的效率及表示长寿命，即本发明的化合物适用在主体层时候跟比较化合物a比明显提高了效率和寿命。
以上的说明是本发明的简单的说明而已，本发明的应用不限于上述举例，对本领域普通技术人员来说，可以根据上述说明范围内加以改进或变换，所有这些改进和变换应属于本发明权利要求的保护范围。假如本发明实施例是为了说明本发明而已，发明内容范围不是限定在这个范围。本发明的保护范围是权利要求所限定的保护范围，跟本发明同等范围的一切技术是包含在本发明的权利范围内。

Claims (5)

1.一种有机发光化合物，其特征在于，具有式(I)结构，
Figure FDA0002739474730000011
其中，
所述A选自式(a-1)、式(a-2)、式(a-3)、式(a-4)、式(a-5)、式(a-6)、式(a-7)、式(a-8)、式(a-9)、式(a-10)、式(a-11)、式(a-12)、式(a-13)、式(a-14)、式(a-15)、式(a-16)、式(a-17)、式(a-18)、式(a-19)、式(a-20)、式(a-21)、式(a-22)或式(a-23)；
式(a-1)-式(a-23)的结构式如下：
Figure FDA0002739474730000012
Figure FDA0002739474730000021
所述Ar选自苯基；
所述Ar1或Ar2为苯基、萘基、联苯基、N-苯基-9H—咔唑基和式(b-1)～式(b-20)中的任意一种：
Figure FDA0002739474730000022
Figure FDA0002739474730000031
n为1。
2.根据权利要求1所述的有机发光化合物，其特征在于，所述有机发光化合物为下述结构中的任意一种：
Figure FDA0002739474730000032
Figure FDA0002739474730000041
Figure FDA0002739474730000051
Figure FDA0002739474730000061
Figure FDA0002739474730000071
3.根据权利要求1或2所述的有机发光化合物的制备方法，其特征在于，包括以下步骤：
将式(II)结构的化合物、含A取代基的溴化物和式(III)结构的化合物混合反应，得到式(I)结构的有机发光化合物：
Figure FDA0002739474730000081
其中，Ar选自苯基，n为1，A、Ar1、Ar2与权利要求1或2中各化合物上的取代基团对应。
4.根据权利要求3所述的有机发光化合物的制备方法，其特征在于，具体包括以下步骤：
氮气条件下，将反应容器里加入含A取代基的溴化物和四氢呋喃，低温-78℃滴加n-丁基锂，加完后继续在-78℃搅拌30min，常温搅拌3h，然后在低温-78℃条件下，滴加溶解在四氢呋喃式(II)所示的苯并蒽酮，滴加以后常温搅拌16小时后停止反应，加入氯化铵水溶液，加入乙酸乙酯萃取有机物，有机层用无水MgSO4干燥后，减压蒸馏去掉有机溶剂，过硅胶柱提纯化合物得到S；
氮气条件下，在反应容器里加S，式(III)所示的化合物及二氯甲烷，在反应体系里，滴加溶解在二氯甲烷的三氟化硼乙醚，常温搅拌2h停止反应，加入甲醇和蒸馏水，用二氯甲烷萃取有机物，有机层用MgSO4干燥，减压蒸馏去掉溶剂，过硅胶柱提纯得到式(I)所示的有机发光化合物；合成路线如下：
Figure FDA0002739474730000091
5.根据权利要求1或2所述的有机发光化合物的应用，其特征在于，所述的有机发光化合物作为空穴传输层材料用于制备有机电致发光器件。
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