CN111909126A - 基于杂蒽衍生物的有机电致发光材料及制备方法与应用 - Google Patents

基于杂蒽衍生物的有机电致发光材料及制备方法与应用 Download PDF

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CN111909126A
CN111909126A CN202010948200.5A CN202010948200A CN111909126A CN 111909126 A CN111909126 A CN 111909126A CN 202010948200 A CN202010948200 A CN 202010948200A CN 111909126 A CN111909126 A CN 111909126A
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organic electroluminescent
layer
ring
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汪康
张雪
王进政
高尚明
刘静
孙艳春
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及基于杂蒽衍生物的有机电致发光材料，化学结构式如式I所示：
Figure DDA0002676023160000011
X独立选自化学键，O，S，Si(R6R7)，C(R8R9)，NR10；R1‑R5各自独立地选自甲基、乙基、丙基、异丙基、叔丁基、烷氧基、芳氧基、苯基、联苯基、或萘基；R6‑R10各自独立地选自甲基、乙基、烷氧基、苯基、杂芳基；L为连接键，或L选自取代或非取代的C6‑C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10‑C30稠环基、取代或非取代的C5‑C30螺环基；Ar1、Ar2各自独立的表示经取代或未经取代的C1‑C30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元到30元杂芳基、取代或未经取代的C10‑C30稠环基、取代或未经取代的C5‑C30螺环基。该材料应用在有机电致发光器件中，能够显著降低驱动电压，提高效率和寿命。

Description

基于杂蒽衍生物的有机电致发光材料及制备方法与应用
技术领域
本发明涉及发光材料技术领域，具体涉及一种基于杂蒽衍生物的有机电致发光材料及制备方法与应用，及以该材料为发光辅助层的有机电致发光器件。
背景技术
有机发光现象是利用有机物质将电能转换为光能的现象。有机电致发光(OLED)是一种自发光装置，其优点在于其提供较宽的视角、较大的对比率以及较快的响应时间。利用有机发光现象的有机电气元件通常具有阳极、阴极及设置在它们之间的有机物层结构。为了提高有机电气元件的效率和稳定性，有机物层通常是由各种不同物质构成的多层结构组成，例如，由空穴注入层、空穴输送层、发光层、电子输送层及电子注入层等组成。然而，空穴传输层材料通常具有低的最高已占据分子轨道(HOMO)值，在发光层中生成的激子扩散到空穴传输层界面或者空穴传输层侧，最终导致在发光层内界面的发光或者发光层内的电荷不均衡，从而在空穴传输层的界面上发光，使有机电致发光器件的色纯度及效率变低，并且寿命变短。
有机电致发光器件的效率、寿命及驱动电压等相互具有关联，若效率增加，则驱动电压相对降低，而在降低驱动电压并驱动时所发生的基于焦耳加热(Joule heating)的有机物质的结晶化减少，最终呈现出寿命提高的倾向，但现有有机电致发光器件受结构限制，如单纯地改善上述有机物层，无法将效率极大化。
近年来，为了解决有机电致发光器件的寿命和效率问题，通常会在空穴输送层和发光层之间加入发光辅助层(多层空穴输送层)。发光辅助层主要起到辅助空穴传输层的作用，因此有时也称为第二空穴传输层。发光辅助层使得从阳极转移的空穴能够平稳地移动到发光层，并且可以阻挡从阴极转移的电子，以将电子限制在发光层内，减少空穴传输层与发光层之间的势垒，降低有机电致发光器件的驱动电压，进一步增加空穴的利用率，从而改善器件的发光效率和寿命。现有有机电致发光器件(OLED)中，空穴传输区域常用的材料主要包括酞菁铜(CuPc)、4，4’-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N，N’-二苯基-N，N’-双(3-甲基苯基)-(1，1’-联苯基)-4，4’-二胺(TPD)、4，4’，4”-三(3-甲基苯基苯基氨基)三苯胺(MTDATA)等。然而，使用这些材料的OLED，由于空穴传输区域中使用的有机材料具有非常高的空穴迁移率，所以可能破坏空穴-电子电荷平衡，导致量子效率(cd/A)降低。另外，当在高电流下驱动OLED时，在阳极与空穴注入层之间出现热应力，热应力显著降低装置的使用寿命。
发明内容
鉴于上述技术问题，本发明的第一个目的在于提供一种基于杂蒽衍生物的有机电致发光材料，以解决现有小分子发光材料驱动电压高，效率低，寿命短的问题。
为实现上述目的，本发明是采用如下技术方案实现的。
基于杂蒽衍生物的有机电致发光材料，其化学结构式如式I所示：
Figure BDA0002676023150000021
X独立选自化学键，O，S，Si(R6R7)，C(R8R9)，NR10；
R1-R10各自独立地选自氢、经取代或未经取代的C1-C30烷基、取代或未经取代的C6-C30芳基、取代或未经取代的3元到30元杂芳基、取代或未经取代的C1-C30烷氧基、取代或未经取代的C6-C30芳基氨基、取代或未经取代的C6-C30芳氧基；R1，R4，R5取代基的位置为在所在苯环的任意位置，R1，R4的个数为0～4，R5的个数为0-3；
L为连接键，或L选自取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C5-C30螺环基；
Ar1、Ar2相同或不同，各自独立的表示经取代或未经取代的C1-C30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元到30元杂芳基、取代或未经取代的C10-C30稠环基、取代或未经取代的C5-C30螺环基、或与相邻取代基连接形成单环或C3-C30脂肪族环或C6-C30芳香族环，其碳原子可置换为氮、氧、硫、硅等杂原子中的一个或以上。
作为本发明的优选，R1-R5各自独立地选自甲基、乙基、丙基、异丙基、叔丁基、烷氧基、芳氧基、苯基、联苯基、或萘基；R6-R10各自独立地选自甲基、乙基、烷氧基、苯基、杂芳基。
作为本发明的进一步优选，该发光材料选自下述结构中的任意一个：
Figure BDA0002676023150000031
Figure BDA0002676023150000041
Figure BDA0002676023150000051
Figure BDA0002676023150000061
Figure BDA0002676023150000071
本发明的第二个目的在于提供上述基于杂蒽衍生物的有机电致发光材料的制备方法，当化学结构式I中L不为化学键时，合成路线如下：
Figure BDA0002676023150000072
具体制备方法包括以下步骤：
步骤1：在反应容器中加入反应物A以及反应物B溶于干燥甲苯之后，在氮气氛围下加入Pd2(dba)3、P(t-Bu)3、t-BuONa；添加后，使反应温度升温到110℃，并且搅拌混合物10h，使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相，接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂；用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:9，获得中间体C；
步骤2：N2保护下，将中间体C、反应物D、四(三苯基膦)钯和碳酸钾分别加入到甲苯、乙醇、水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤出去盐，再用少量乙醇淋洗，干燥滤饼，置于1,4-二氧六环中重结晶，得到通式I所示的化合物；
当化学结构式I中L为化学键时，合成路线如下：
Figure BDA0002676023150000081
具体制备方法为：在反应容器中加入反应物a以及反应物b溶于干燥甲苯之后，在氮气氛围下加入Pd2(dba)3、P(t-Bu)3、t-BuONa；添加后，使反应温度升温到110℃，并且搅拌混合物10h，使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相；接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:9，获得通式I所示化合物。
本发明的第三个目的在于提供上述式I所示的小分子有机电致发光材料作为发光辅助层材料、空穴传输层材料，在制作有机电致发光器件领域的应用。
本发明的第四个目的在于提供一种有机电致发光器件，其结构包括从下而上依次叠加的ITO玻璃基板、空穴注入层、空穴传输层、发光辅助层、发光层、空穴阻挡层、电子传输层、电子注入层和阴极层，所述发光辅助层中包含上述式I所示的有机电致发光材料。
作为本发明的优选，所述空穴注入层是厚度为45nm的化合物mCP与F4-TCNQ，所述mCP与F4-TCNQ掺杂比为97:3；所述空穴传输层是厚度为50nm的化合物mCP，所述发光辅助层是厚度为20nm的式I所示的有机电致发光材料；所述发光层是厚度为20nm的主体材料CBP和掺杂材料(btfmp)2Ir(dbm)，主体材料和掺杂材料的重量比为95:5；所述空穴阻挡层是厚度为10nm的BAlq；所述电子传输层是厚度为40nm的Alq3；所述电子注入层是厚度为0.5nm氟化锂。
本发明的优点和有益效果：
(1)本发明提供的发光材料在杂蒽上并上两个苯，同时用芳胺衍生物对母核结构进行性能调整，进一步改变杂蒽并苯的扭曲结构，该母核结构作为发光辅助材料在有机电致发光器件中显示了优异的稳定性，具有合适的HOMO和LUMO能级，能够显著提高有机电致发光器件的使用寿命。
(2)本发明的发光材料制备方法简单，原料易得，得到的粗品容易提纯，可得到高纯度的发光辅助材料，适合工业化生产。
(3)利用本发明的发光材料制备的有机电致发光器件的驱动电压大幅降低，寿命和效率显著提升，这些性能上的显著效果使材料满足量产的条件。
具体实施方式
下面将结合本申请实施例对本申请的技术方案进行清楚、完整地描述，显然，所描述的实施例仅是本申请一部分实施例，而不是全部的实施例。基于本申请中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本申请保护的范围。
一种基于杂蒽衍生物的有机电致发光材料，其化学结构式如式I所示：
Figure BDA0002676023150000091
X独立选自化学键，O，S，Si(R6R7)，C(R8R9)，NR10；
R1-R10各自独立地选自氢、经取代或未经取代的C1-C30烷基、取代或未经取代的C6-C30芳基、取代或未经取代的3元到30元杂芳基、取代或未经取代的C1-C30烷氧基、取代或未经取代的C6-C30芳基氨基、取代或未经取代的C6-C30芳氧基；R1，R4，R5取代基的位置为在所在苯环的任意位置，R1，R4的个数为0～4，R5的个数为0-3；
L为连接键，或L选自取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C5-C30螺环基；
Ar1、Ar2相同或不同，各自独立的表示经取代或未经取代的C1-C30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元到30元)杂芳基、取代或未经取代的C10-C30稠环基、取代或未经取代的C5-C30螺环基、或与相邻取代基连接形成单环或多环(C3-C30)脂肪族环或(C6-C30)芳香族环，其碳原子可置换为氮、氧、硫、硅等杂原子中的一个或以上。
进一步，R1-R5各自独立地选自甲基、乙基、丙基、异丙基、叔丁基、烷氧基、芳氧基、苯基、联苯基、或萘基；R6-R10各自独立地选自甲基、乙基、烷氧基、苯基、杂芳基。
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。
实施例1化合物2的合成
合成路线：
Figure BDA0002676023150000101
具体合成方法：
步骤1：在反应容器中加入化学式反应物A-2(50mmol)和反应物B-2(55mmol)溶于200ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后，使反应温度缓慢(1小时)升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚＝1:9作为洗脱剂(体积比)，用管柱色谱法纯化剩余物质，获得中间体C-2(15.6g，产率为75％，Ms:417.17)。
步骤2：N2保护下，将中间体C-2(35mmol)、中间体D-2(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤出去盐，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(150mL)，得到终产品2(20.3g，产率为82％，MS：709.30)。
注：反应物D-2是参照J.Org.Chem.2017,82,4964-4969、CN105968045A公开的方法进行合成的。
实施例2化合物29的合成
合成路线：
Figure BDA0002676023150000111
具体合成方法：
步骤1：在反应容器中加入化学式反应物A-29(50mmol)和反应物B-29(55mmol)溶于200ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后，使反应温度缓慢(1小时)升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚＝1:9作为洗脱剂(体积比)，用管柱色谱法纯化剩余物质，获得中间体C-29(15.0g，产率为72％，MS：415.17)。
步骤2：N2保护下，将中间体C-29(35mmol)、中间体D-29(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤出去盐，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(150mL)，得到终产品29(21.3g，产率为84％，MS：725.28)。
注：反应物D-29是参照J.Org.Chem.2017,82,4964-4969、CN105968045A公开的方法进行合成的。
实施例3化合物51的合成
合成路线：
Figure BDA0002676023150000121
具体合成方法：
步骤1：在反应容器中加入化学式反应物A-51(50mmol)和反应物B-51(55mmol)溶于200ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后，使反应温度缓慢(1小时)升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚＝1:9作为洗脱剂(体积比)，用管柱色谱法纯化剩余物质，获得中间体C-51(17.0g，产率为77％，Ms:441.19)。
步骤2：N2保护下，将中间体C-51(35mmol)、中间体D-51(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤出去盐，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(150mL)，得到终产品51(21.2g，产率为83％，MS：731.36)。
注：反应物D-51是参照J.Org.Chem.2017,82,4964-4969、CN105968045A公开的方法进行合成的。
实施例4化合物65的合成
合成路线：
Figure BDA0002676023150000131
具体合成方法：
步骤1：在反应容器中加入化学式反应物A-65(50mmol)和反应物B-65(55mmol)溶于200ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后，使反应温度缓慢(1小时)升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚＝1:9作为洗脱剂(体积比)，用管柱色谱法纯化剩余物质，获得中间体C-65(16.9g，产率为76％，Ms:445.18)。
步骤2：N2保护下，将中间体C-65(35mmol)、中间体D-65(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤出去盐，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(150mL)，得到终产品65(20.4g，产率为84％，MS：693.30)。
注：反应物D-65是参照J.Org.Chem.2017,82,4964-4969、CN105968045A公开的方法进行合成的。
实施例5化合物83的合成
合成路线：
Figure BDA0002676023150000141
具体合成方法：
步骤1：在反应容器中加入化学式反应物A-83(50mmol)和反应物B-83(55mmol)溶于200ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后，使反应温度缓慢(1小时)升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚＝1:9作为洗脱剂(体积比)，用管柱色谱法纯化剩余物质，获得中间体C-83(17.4g，产率为78％，Ms:445.18)。
步骤2：N2保护下，将中间体C-83(35mmol)、中间体D-83(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤出去盐，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(150mL)，得到终产品83(23.2g，产率为83％，MS：798.36)。
注：反应物D-83是参照J.Org.Chem.2017,82,4964-4969、CN105968045A公开的方法进行合成的。
实施例6化合物90的合成
合成路线：
Figure BDA0002676023150000151
具体合成方法：
步骤1：在反应容器中加入化学式反应物A-90(50mmol)和反应物B-90(55mmol)溶于200ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后，使反应温度缓慢(1小时)升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚＝1:9作为洗脱剂(体积比)，用管柱色谱法纯化剩余物质，获得中间体C-90(18.3g，产率为77％，Ms:476.42)。
步骤2：N2保护下，将中间体C-90(35mmol)、中间体D-90(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中，升温至100℃回流反应8h，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤出去盐，再用少量乙醇淋洗，干燥滤饼。置于1,4-二氧六环中重结晶(150mL)，得到终产品90(22.2g，产率为85％，MS：747.33)。
注：反应物D-90是参照J.Org.Chem.2017,82,4964-4969、CN105968045A公开的方法进行合成的。
实施例7至实施例22
参照实施例1至6的合成方法完成对化合物6、18、23、34、45、55、62、68、74、78、80、85、88、92、95、98的合成，质谱和分子式列于下表1。
表1：
实施例 化合物 分子式 质谱理论值 质谱测试值
实施例7 6 C<sub>52</sub>H<sub>37</sub>NO 691.29 691.57
实施例8 18 C<sub>56</sub>H<sub>40</sub>N<sub>2</sub>O 756.95 756.96
实施例9 23 C<sub>68</sub>H<sub>63</sub>NO 910.26 910.47
实施例10 34 C<sub>51</sub>H<sub>37</sub>NS 695.26 695.83
实施例11 45 C<sub>56</sub>H<sub>40</sub>N<sub>2</sub>S 772.29 772.21
实施例12 55 C<sub>51</sub>H<sub>37</sub>N 663.29 663.58
实施例13 62 C<sub>60</sub>H<sub>41</sub>N 775.32 775.24
实施例14 68 C<sub>47</sub>H<sub>23</sub>D<sub>12</sub>N 625.35 625.37
实施例15 74 C<sub>73</sub>H<sub>55</sub>N 945.43 945.16
实施例16 78 C<sub>67</sub>H<sub>55</sub>N 873.43 873.30
实施例17 80 C<sub>66</sub>H<sub>46</sub>N<sub>2</sub> 866.37 866.44
实施例18 85 C<sub>69</sub>H<sub>63</sub>N<sub>3</sub> 933.50 933.76
实施例19 88 C<sub>49</sub>H<sub>41</sub>NSi 671.30 671.22
实施例20 92 C<sub>53</sub>H<sub>43</sub>NSi 721.32 721.23
实施例21 95 C<sub>58</sub>H<sub>49</sub>NSi 787.36 787.18
实施例22 98 C<sub>59</sub>H<sub>44</sub>N<sub>2</sub>O 796.35 796.53
实施例23
Figure BDA0002676023150000171
具体合成方法：
在反应容器中加入化学式反应物A-27(50mmol)和反应物B-27(55mmol)溶于200ml甲苯之后，在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后，使反应温度缓慢(1小时)升温到110℃，并且搅拌混合物10h。使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂。以二氯甲烷：石油醚＝1:9作为洗脱剂(体积比)，用管柱色谱法纯化剩余物质，获得产物27(30.0g，产率为80％，Ms:749.28)。
注：A-27合成方法参照专利KR1020190122078A；B-27合成方法参照J.Org.Chem.2017,82,4964-4969、CN105968045A；
另外，需要说明，本申请其他化合物参照上述所列举的实施例的合成方法即可获得，所以在此不再一一例举。
实施例24制造含有化合物2的有机电致发光器件
将涂层厚度为150nm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。
将已经准备好的ITO透明电极上蒸镀厚度为45nm的化合物mCP与F4-TCNQ(掺杂比为97:3)作为空穴注入层。然后将化合物mCP在形成的空穴注入层上面真空蒸镀厚度为50nm的空穴传输层。在上述空穴传输层上蒸镀厚度为20nm的化合物2作为发光辅助层；
然后在上述发光辅助层上蒸镀厚度为20nm的主体材料CBP和掺杂材料(btfmp)2Ir(dbm)。主体材料和掺杂材料的重量比为95:5。接着在上述发光层上真空蒸镀厚度为10nm的BAlq作为空穴阻挡层及厚度为40nm的电子传输层Alq3。在上述电子传输层上真空蒸镀厚度为0.5nm氟化锂(LiF)，作为电子注入层。最后蒸镀厚度为150nm的铝作为阴极，以此完成了有机电致发光器件的制备。
上述原料的化学结构式如下所示：
Figure BDA0002676023150000181
实施例25-实施例46
将实施例24中的化合物2分别置换为化合物6，18，23，27，29，34，45，51，55，62，65，68，74，78，80，83，85，88，90，92，95，98，其他方法相同，分别制作含有化合物2，6，18，23，27，29，34，45，51，55，62，65，68，74，78，80，83，85，88，90，92，95，98的有机电致发光器件。
对比例1
制造含有对比化合物1的有机电致发光器件。按照实施例24的方法，将发光辅助层的化合物2置换为对比化合物1，其他方法相同，制作含有对比化合物1的有机电致发光器件。
Figure BDA0002676023150000182
对比例2
制造含有对比化合物2的有机电致发光器件。按照器件实施例1的方法，将发光辅助层的化合物2置换为对比化合物2，其他方法相同，制作含有对比化合物2的有机电致发光器件。
Figure BDA0002676023150000191
对比例3
制造含有对比化合物3的有机电致发光器件。按照器件实施例1的方法，将发光辅助层的化合物2置换为对比化合物3，其他方法相同，制作含有对比化合物3的有机电致发光器件。
Figure BDA0002676023150000192
对比例4
按照器件实施例1的方法，制作器件对比例4，不同之处在于不含有发光辅助层。
表2为本发明实施例24～45的器件以及对比例1～4的器件发光特性测试结果(亮度值为5000cd/m2)。
Figure BDA0002676023150000193
Figure BDA0002676023150000201
由表2可以看出，使用本发明提供化合物作为发光辅助层材料所制备的有机电致发光器件与使用对比化合物1、2作为发光辅助层材料以及不使用发光辅助层的有机电致发光器件相比，驱动电压，发光效率以及寿命得到显著提高。
从器件数据发现，与结构相似的对比化合物3相比，虽然本发明的发光辅助层化合物与对比化合物3的结构相似，区别在于母核上的杂原子数不同，但是驱动电压，发光效率，寿命都要显著提升，这种情况产生的原因可能是母核上R2，R3取代的存在改变杂蒽并苯的扭曲结构，使其具有合适的HOMO和LUMO能级。在器件性能上体现为具有两个氧原子的杂蒽母核的对比化合物3驱动电压增加0.4左右，效率下降，尤其是寿命降低约20h。
并且与对比例1-2相比，驱动电压下降0.8-2.1V，发光效率提升约7-18.4％，同时器件寿命提高约15-50h，寿命在138h以上。
本领域的技术人员将明显看到，在不脱离本发明的精神和范围下，本发明可以有许多修改和变化。因此可以预期到，本发明覆盖在附带权利要求的范围及其相当范围内提供的本发明修改和变化。
对所公开的实施例的上述说明，使本领域专业技术人员能够实现或者使用本发明。对这些实施例的多种修改对本领域的技术人员来说将是显而易见的，本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下，在其他实施例中实现。因此，本发明将不会被限制与本文所示的这些实施例，而是符合与本文所公开的原理和新颖特点相一致的最宽的范围。

Claims (7)

1.基于杂蒽衍生物的有机电致发光材料，其特征在于，其化学结构式如式I所示：
Figure FDA0002676023140000011
X独立选自化学键，O，S，Si(R6R7)，C(R8R9)，NR10；
R1-R10各自独立地选自氢、经取代或未经取代的C1-C30烷基、取代或未经取代的C6-C30芳基、取代或未经取代的3元到30元杂芳基、取代或未经取代的C1-C30烷氧基、取代或未经取代的C6-C30芳基氨基、取代或未经取代的C6-C30芳氧基；R1，R4，R5取代基的位置为在所在苯环的任意位置，R1，R4的个数为0～4，R5的个数为0-3；
L为连接键，或L选自取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C5-C30螺环基；
Ar1、Ar2相同或不同，各自独立的表示经取代或未经取代的C1-C30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元到30元杂芳基、取代或未经取代的C10-C30稠环基、取代或未经取代的C5-C30螺环基、或与相邻取代基连接形成单环或C3-C30脂肪族环或C6-C30芳香族环，其碳原子可置换为氮、氧、硫、硅等杂原子中的一个或以上。
2.根据权利要求1所述的基于杂蒽衍生物的有机电致发光材料，其特征在于，R1-R5各自独立地选自甲基、乙基、丙基、异丙基、叔丁基、烷氧基、芳氧基、苯基、联苯基、或萘基；R6-R10各自独立地选自甲基、乙基、烷氧基、苯基、杂芳基。
3.根据权利要求1所述的基于杂蒽衍生物的有机电致发光材料，其特征在于，该发光材料选自下述结构中的任意一个：
Figure FDA0002676023140000021
Figure FDA0002676023140000031
Figure FDA0002676023140000041
Figure FDA0002676023140000051
Figure FDA0002676023140000061
4.权利要求1所述的基于杂蒽衍生物的有机电致发光材料的制备方法，其特征在于，当权利要求1化学结构式I中L不为化学键时，合成路线如下：
Figure FDA0002676023140000062
具体制备方法包括以下步骤：
步骤1：在反应容器中加入反应物A以及反应物B溶于干燥甲苯之后，在氮气氛围下加入Pd2(dba)3、P(t-Bu)3、t-BuONa；添加后，升温，并且搅拌混合物，使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相，接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂；用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:9，获得中间体C；
步骤2：N2保护下，将中间体C、反应物D、四(三苯基膦)钯和碳酸钾分别加入到甲苯、乙醇、水的混合溶剂中，升温，回流反应，反应结束后，冷却至室温，待固体析出完毕后，抽滤后用水洗涤出去盐，再用少量乙醇淋洗，干燥滤饼，置于1,4-二氧六环中重结晶，得到通式I所示的化合物；
当权利要求1化学结构式I中L为化学键时，合成路线如下：
Figure FDA0002676023140000071
具体制备方法为：在反应容器中加入反应物a以及反应物b溶于干燥甲苯之后，在氮气氛围下加入Pd2(dba)3、P(t-Bu)3、t-BuONa；添加后，升温，并且搅拌混合物，使用硅藻土趁热抽滤，除去盐和催化剂，滤液冷却至室温后，接着将蒸馏水添加到滤液中进行洗涤，分液后保留有机相，用乙酸乙酯萃取水相；接着使用硫酸镁干燥合并后的有机层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质，洗脱剂体积比为二氯甲烷：石油醚＝1:9，获得通式I所示化合物。
5.权利要求1所述的基于杂蒽衍生物的有机电致发光材料作为发光辅助层材料、空穴传输层材料，在制作有机电致发光器件领域的应用。
6.一种有机电致发光器件，其结构包括：从下而上依次叠加的ITO玻璃基板、空穴注入层、空穴传输层、发光辅助层、发光层、空穴阻挡层、电子传输层、电子注入层和阴极层，其特征在于，所述发光辅助层中包含权利要求1中式I所示的有机电致发光材料。
7.根据权利要求6所述的一种有机电致发光器件，其特征在于，所述空穴注入层是厚度为45nm的化合物mCP与F4-TCNQ，所述mCP与F4-TCNQ掺杂比为97:3；所述空穴传输层是厚度为50nm的化合物mCP，所述发光辅助层是厚度为20nm的式I所示的有机电致发光材料；所述发光层是厚度为20nm的主体材料CBP和掺杂材料(btfmp)2Ir(dbm)，主体材料和掺杂材料的重量比为95:5；所述空穴阻挡层是厚度为10nm的BAlq；所述电子传输层是厚度为40nm的Alq3；所述电子注入层是厚度为0.5nm氟化锂。
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