CN110642666B - 一种蓝色荧光主体化合物及其制备方法和器件 - Google Patents

一种蓝色荧光主体化合物及其制备方法和器件 Download PDF

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CN110642666B
CN110642666B CN201910924126.0A CN201910924126A CN110642666B CN 110642666 B CN110642666 B CN 110642666B CN 201910924126 A CN201910924126 A CN 201910924126A CN 110642666 B CN110642666 B CN 110642666B
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马晓宇
金成寿
赵贺
高尚明
于丹阳
张颖
张思铭
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Olide Shanghai Photoelectric Material Technology Co ltd
Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明涉及一种蓝色荧光主体化合物及其制备方法和器件，所述蓝色荧光主体化合物的其结构式如化学式1所示：

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一种蓝色荧光主体化合物及其制备方法和器件
技术领域
本发明涉及发光材料技术领域，具体涉及一种蓝色荧光主体化合物及其制备方法和器件。
背景技术
2000年以来，OLED被誉为第三代显示技术，由于其具有其他显示技术不可比拟的优良性能，受到了业界的极大关注。信息科学与技术的飞速发展，使得人们对信息显示器件的要求越来越高，特别是高品质图像即高分辨率、高对比度、高响应速度、宽视角，以及便携性即超薄、超轻、低功耗，成为未来信息显示的发展方向，而OLED恰恰满足了以上的各种需求。
OLED作为发光机理迥异的电致发光材料，是在电场作用下而产生的发光现象，是一个将电能直接转化为光能的发光过程。
与其他显示技术相比，OLED具备诸多优势，如材料选择范围广、发光亮度和效率高、可以实现蓝光到红光光谱区域的全彩色显示、视角宽、驱动电压低、制作过程相对简单，成本低，同时最具特色的是其可实现柔性显示。OLED能满足当今信息时代对显示设备更高性能和更大信息容量的要求，所以开发更高性能的OLED材料势在必行。
发明内容
本发明的目的是提供一种蓝色荧光主体化合物及其制备方法和器件。与常规材料相比本发明提供的化合物具有能显示优异电致发光性质、长的器件寿命和适当色坐标。
为了实现上述目的，本发明的技术方案具体如下：
本发明提供一种蓝色荧光主体化合物，其结构式如化学式1所示：
Figure BDA0002218410100000021
化学式1中，Ra和Rb各自独立地表示：氢、氢的同位素、卤素、氰基、羧基、硝基、羟基、磺酸基、磷酸基、硼烷基、取代或非取代的硅基、取代或非取代的C1-C60烷基、取代或非取代的C6-C60芳基、取代或非取代的C3-C60杂芳基、取代或非取代的C3-C60环烷基、取代或非取代的C1-C60烷氧基、取代或非取代的C1-C60烷基氨基、取代或非取代的C6-C60芳基氨基、取代或非取代的C6-C60芳氧基、或者取代或非取代的C6-C60芳硫基；或与相邻取代基连接形成经取代或未经取代的单环或多环，具体为C3-C30的脂肪族环或芳香族环；
m、n为0～4的整数；
L1、L2为连接键、或者各自独立地表示为取代或非取代的C1～C60烷基、取代或非取代的C3～C60的环烷基、取代或非取代的C6～C60芳基、或者取代或非取代的C6～C60杂环基；或与相邻取代基连接形成经取代或未经取代的单环或多环，具体为C3-C30的脂肪族环或芳香族环；优选L1、L2为连接键或苯基；
Ar为取代或非取代的C1-C60烷基、取代或非取代的C6-C60芳基、取代或非取代的C3-C60杂芳基、取代或非取代的C3-C60环烷基、取代或非取代的C1-C60烷基氨基、取代或非取代的C6-C60芳基氨基、取代或非取代的C6-C60芳氧基、或者取代或非取代的C6-C60芳硫基；或与相邻取代基连接形成经取代或未经取代的单环或多环，具体为C3-C30的脂肪族环或芳香族环；优选Ar为取代或非取代的C1-C60烷基、取代或非取代的C6-C60芳基、取代或非取代的C3-C60杂芳基、取代或非取代的C3-C60环烷基、取代或非取代的C1-C60烷基氨基、或者取代或非取代的C6-C60芳基氨基；进一步优选Ar为取代或非取代的C6-C60芳基、取代或非取代的C3-C60杂芳基、或者取代或非取代的C6-C60芳基氨基；
A如化学式2所示：
Figure BDA0002218410100000031
化学式2中：
Ar1、Ar2各自独立地表示为氰基、取代或非取代的C1～C60烷基、取代或非取代的C3～C60环烷基、取代或非取代的C2～C60烯基、取代或非取代的C3～C60环烯基、取代或非取代的C3～C60炔基、取代或非取代的C3～C60环炔基、取代或非取代的C6～C60芳基、或者取代或非取代的C6～C60的杂环基；或者Ar1、Ar2之间连接形成经取代或未经取代的单环或多环，具体为C3-C30的脂肪族环或芳香族环；优选Ar1、Ar2为C1～C60的烷基、取代或非取代的C6～C60的芳基、或者C6～C60的杂环基，或者Ar1、Ar2之间连接形成经取代或未经取代的单环或多环。
Rc和Rd各自独立地表示：氢、氢的同位素、卤素、氰基、羧基、硝基、羟基、磺酸基、磷酸基、硼烷基、取代或非取代的硅基、取代或非取代的C1-C60烷基、取代或非取代的C6-C60芳基、取代或非取代的C3-C60杂芳基、取代或非取代的C3-C60环烷基、取代或非取代的C1-C60烷氧基、取代或非取代的C1-C60烷基氨基、取代或非取代的C6-C60芳基氨基、取代或非取代的C6-C60芳氧基、或者取代或非取代的C6-C60芳硫基；或与相邻取代基连接形成经取代或未经取代的单环或多环，具体为C3-C30的脂肪族环或芳香族环；
p、q为0～3的整数；
Figure BDA0002218410100000041
代表与L1的连接键，为化学式2上的任意位置。
在上述技术方案中，当Ra和Rb分别与相邻取代基连接形成经取代或未经取代的单环或多环时，其碳原子可被置换成至少一个选自氮、氧、硫的杂原子；当L1、L2分别与相邻取代基连接形成经取代或未经取代的单环或多环时，其碳原子可被置换成至少一个选自氮、氧、硫的杂原子；当Ar与相邻取代基连接形成经取代或未经取代的单环或多环时，其碳原子可被置换成至少一个选自氮、氧、硫的杂原子；当Ar1、Ar2之间连接形成经取代或未经取代的单环或多环时，其碳原子可被置换成至少一个选自氮、氧、硫的杂原子；当Rc和Rd分别与相邻取代基连接形成经取代或未经取代的单环或多环时，其碳原子可被置换成至少一个选自氮、氧、硫的杂原子。
在上述技术方案中，优选A为如下结构：
Figure BDA0002218410100000042
Figure BDA0002218410100000051
其中，R的范围与Rc相同，R的取代数量为0个或者多个。
在上述技术方案中，Ar更具体的优选为苯基、二联苯基、三联苯基、萘基、蒽基、菲基、芘基、芴、螺、咔唑基、呋喃基、噻吩基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、喹唑啉、苯并咪唑、吖啶、吖啶衍生物、噁唑、噻唑、吩噻嗪、喹唑啉、喹喔啉、异丙基、环己基和叔丁基中的一种。
在上述技术方案中，Ar进一步优选自下述结构中的任意一个：
Figure BDA0002218410100000052
Figure BDA0002218410100000061
其中：R为氢、卤素、氰基、C1-C30烷基、C6-C50芳基、C7-C50芳烷基、C7-C50芳基、烷氧基、C7-C50芳基、烷巯基或C5-C50杂芳基；且所述—R表示在其所在苯环的任意位置，“*”为连接位置。
在上述技术方案中，最优选所述蓝色荧光主体化合物选自以下结构，但是不限于这些化合物：
Figure BDA0002218410100000062
Figure BDA0002218410100000071
Figure BDA0002218410100000081
Figure BDA0002218410100000091
Figure BDA0002218410100000101
Figure BDA0002218410100000111
Figure BDA0002218410100000121
Figure BDA0002218410100000131
本发明还提供一种蓝色荧光主体化合物的制备方法，包括以下步骤：
步骤1、中间体1的制备
将化合物1加至苯中搅拌至溶解毕，加入NBS，加毕，加热至回流，待反应毕，抽滤后浓缩的产品经硅胶漏斗及重结晶得到中间体1；
步骤2、中间体2的制备
将中间体1用乙腈溶解后，加入三苯基膦加热搅拌，反应结束后，用丙酮洗涤产品，抽滤得中间体2；
步骤3、中间体3的制备
将将中间体2用THF溶解后，再加入KOt-Bu并搅拌后加入化合物2，反应结束后，用甲醇淬灭，再用二氯和纯水进行分液萃取，有机相用无水MgSO4干燥，浓缩的有机相经硅胶漏斗及重结晶得到中间体3；
步骤4、中间体4的制备
在N2保护下，将三环己基膦、及三(二亚苄基丙酮)二钯加至二氧六环中，并于常温搅拌，随后将联硼酸频那醇酯和醋酸钾加入至体系中搅拌，最后加入中间体3并升温至回流至过夜，反应结束后，降至室温后，加入乙酸乙酯和超纯水进行分液，有机相用无水MgSO4干燥，浓缩的有机相经硅胶漏斗及重结晶得到中间体4；
步骤5、化学式1所示化合物的制备
将中间体4、化合物3、碳酸钾加入到1,4-二氧六环/水的混合溶剂中，使用氮气置换空气三次，加入四(三苯基磷)钯，再次用氮气置换空气三次，在氮气保护下加热，TLC监测；待反应结束后，在氮气保护下冷却至室温；使用分液漏斗进行分液，保留有机相；使用硅藻土除去催化剂，用DCM洗硅藻土至无产品；浓缩滤液至少量，硅胶拌样，使用硅胶漏斗进行分离，得到化学式1所示化合物；
其合成路线如下：
Figure BDA0002218410100000141
式中，Hal为卤素，其余取代基团与化学式1中的限定一致，这里不再赘述。
本发明提供的化学式1所示化合物还可以通过下述路线合成：
Figure BDA0002218410100000151
。
本发明还提供一种包含化学式1所示的化合物的有机发光器件。
所述有机发光器件包括相对设置的阳极、阴极，以及位于所述阳极与所述阴极之间的有机层；所述有机层包含本发明化学式1所示的化合物。
其中，所述有机层至少包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种；所述空穴注入层、所述空穴传输层、所述发光层、所述电子传输层、所述电子注入层中的至少一层的材料为本发明化学式1所示的化合物。
所述有机层中包含有化学式1所示的化合物；化学式1所示的化合物是单一形态或与其它物质混合存在于有机层中。
当本发明化学式1所示的化合物存在于所述有机层中的发光层时，本发明化学式1所示的化合物可以作为发光主体或者掺杂在其它荧光主体中。
当本发明化学式1所示的化合物存在于所述有机层中的空穴传输层或者空穴注入层时，本发明化学式1所示的化合物可以作为空穴传输层、空穴注入层以及既具备空穴注入又具备空穴传输功能层。
当本发明化学式1所示的化合物存在于所述有机层中的电子传输层或者电子注入层时，本发明化学式1所示的化合物可以作为电子传输层、电子注入层以及既具备电子注入又具备电子传输功能层。
本发明所述的包含有本发明化学式1所示的化合物制备的器件可以用于有机发光器件(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(OTFT)。
本发明所述的器件可以通过薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属以及具有导电性的氧化物及他们的合金形成阳极，也可以采用旋转涂膜(spin-coating)或薄带带头蒸镀；还可以采用成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等方法减少层数制造。
本发明的又一方面还提供一种显示装置，其包括如上所述的有机发光器件。
本发明的有益效果是：
本发明提供的蓝色荧光主体化合物，与常规材料相比本发明提供的化合物具有能显示优异电致发光性质、长的器件寿命和适当色坐标。
用本发明提供的蓝色荧光主体化合物制备的有机发光器件，由于使用化学式1所示的新型化合物，使本发明的器件成为可以达成高效率、长寿命的有机发光器件。
本发明提供的蓝色荧光主体化合物的制备方法，工艺简单，产率较高。
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。
实施例1：中间体B-1的制备
Figure BDA0002218410100000171
中间体B-1的合成：将2-溴芴A-1(24.51g，100mmol)加至苯中搅拌至，溶解毕，缓慢加入NBS(17.79g，100mmol)，加毕，加热至回流，待反应毕，抽滤后浓缩的产品经硅胶漏斗及重结晶得到产品B-1 24.5g(收率：76％)。
表1实施例1反应原料以及产物结构及表征汇总
Figure BDA0002218410100000172
Figure BDA0002218410100000181
实施例2：中间体C-1的制备
Figure BDA0002218410100000182
中间体C-1的合成：将上述反应中得到的中间体B-1(24.5g，75.613mmol)用乙腈溶解后，加入三苯基膦(21.82，83.174mmol)并于80℃加热搅拌。反应结束后，用丙酮洗涤产品，抽滤得中间体C-1 8 37.6g(85％)。
Figure BDA0002218410100000183
Figure BDA0002218410100000191
实施例3：中间体E-1的制备
Figure BDA0002218410100000192
中间体E-1的合成：将上述反应得到的中间体C-1(37.6g，64.12mmol)用THF溶解后，于0℃缓慢加入1.0M KOt-Bu(64.12mL，64.12mmol)并搅拌30min后加入苯甲酮(11.68g，64.12mmol)，加毕缓慢升温至常温继续搅拌，反应结束后，用甲醇淬灭，再用二氯和纯水进行分液萃取。有机相用无水MgSO4干燥。浓缩的有机相经硅胶漏斗及重结晶得到中间体E-121.4g(收率：82％)。
Figure BDA0002218410100000193
Figure BDA0002218410100000201
实施例4：中间体F-1的制备
Figure BDA0002218410100000202
中间体F-1的合成：在N2保护下，将三环己基膦(0.73g，2.62mmol)、三(二亚苄基丙酮)二钯(2.39g,2.62mmol)加至二氧六环中，并于常温搅拌约30min.随后将联硼酸频那醇酯(13.94g，54.89mmol)和醋酸钾(10.26g，104.56mmol)加入至体系中搅拌约10分钟，最后加入上述得到的中间体E-1(21.4g，52.28mmol)并缓慢升温至回流至过夜。反应结束后，降至室温后，加入乙酸乙酯和超纯水进行分液，有机相用无水MgSO4干燥。浓缩的有机相经硅胶漏斗及重结晶得到中间体F-1 20.5g(收率：86％)。
Figure BDA0002218410100000211
Figure BDA0002218410100000221
实施例5：化合物1的制备
Figure BDA0002218410100000222
化合物1的合成：
将中间体F-1(20.3g 44.5mmol)、中间体G-1(14.77g 44.5mmol)、碳酸钾(18.4g133.5mmol)加入到500mL 1,4-二氧六环/水(体积比4:1)的混合溶剂中。使用氮气置换空气三次，加入四(三苯基磷)钯(2.57g 2.23mmol)，再次用氮气置换空气三次，在氮气保护下加热到90℃。TLC监测。待反应结束后，在氮气保护下冷却至室温。使用分液漏斗进行分液，保留有机相。使用硅藻土除去催化剂，用DCM洗硅藻土至无产品。浓缩滤液至少量，硅胶拌样，使用硅胶漏斗进行分离，得到化合物1 20.23g(收率：78％)。
Figure BDA0002218410100000231
Figure BDA0002218410100000241
使用本发明的蓝色荧光主体化合物制造OLED
器件实施例1：
将费希尔公司涂层厚度为
Figure BDA0002218410100000242
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50nm的4,4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)作为空穴注入层。
Figure BDA0002218410100000251
在形成的空穴注入层上面真空蒸镀厚度为30nm的N'-二(1-萘基)-N,N'-二苯基-(1,1'-联苯)-4,4'-二胺(a-NPD)作为空穴传输层。
Figure BDA0002218410100000252
然后在上述空穴传输层上蒸镀厚度为30nm的主体材料本发明的化合物1和掺杂材料4,4'-双[4-(二对甲苯基氨基)苯乙烯基]联苯(DPAVBi)。
Figure BDA0002218410100000253
接着在上述发光层上真空蒸镀厚度为10nm的双(2-甲基-8-羟基喹啉-N1，08)-(1,1’-联苯-4-羟基)铝(BAlq)作为空穴阻挡层。
Figure BDA0002218410100000254
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。
[实施例2]除了用化合物8代替主体材料化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
[器件实施例3]除了用化合物22代替主体材料化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
[器件实施例4]除了用化合物39代替主体材料化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
[器件实施例5]除了用化合物50代替主体材料化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
[器件实施例6]除了用化合物56代替主体材料化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
[器件实施例7]除了用化合物57代替主体材料化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
[器件实施例8]除了用化合物90代替主体材料化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
[器件实施例9]除了用化合物95代替主体材料化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
[器件比较例1]除了用化合物9,10-双-(1-萘基)蒽(ADN)代替化合物1以外，用与实施例1相同的方法制备有机电致发光器件。
Figure BDA0002218410100000271
制造的OLED的电致发光性质
评价根据器件实施例1到器件实施例9和器件比较例1制造的每个有机电致发光器件的效率和寿命。
Figure BDA0002218410100000272
因此，施用了本发明的化合物作为主体材料的器件在色纯度方面显示显著的改进。在色纯度和发光效率两个方面的改进证实本发明的材料具有优异的性质。
显然，上述实施例仅仅是为清楚地说明所作的举例，而并非对实施方式的限定。对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。

Claims (3)

1.一种蓝色荧光主体化合物，其特征在于，其选自以下结构：
Figure FDA0003700286860000011
Figure FDA0003700286860000021
Figure FDA0003700286860000031
Figure FDA0003700286860000041
2.根据权利要求1所述的蓝色荧光主体化合物的制备方法，其特征在于，包括以下步骤：
步骤1、中间体1的制备
将化合物1加至苯中搅拌至溶解毕，加入NBS，加毕，加热至回流，待反应毕，抽滤后浓缩的产品经硅胶漏斗及重结晶得到中间体1；
步骤2、中间体2的制备
将中间体1用乙腈溶解后，加入三苯基膦加热搅拌，反应结束后，用丙酮洗涤产品，抽滤得中间体2；
步骤3、中间体3的制备
将中间体2用THF溶解后，再加入KOt-Bu并搅拌后加入化合物2，反应结束后，用甲醇淬灭，再用二氯和纯水进行分液萃取，有机相用无水MgSO4干燥，浓缩的有机相经硅胶漏斗及重结晶得到中间体3；
步骤4、中间体4的制备
在N2保护下，将三环己基膦、及三(二亚苄基丙酮)二钯加至二氧六环中，并于常温搅拌，随后将联硼酸频那醇酯和醋酸钾加入至体系中搅拌，最后加入中间体3并升温至回流至过夜，反应结束后，降至室温后，加入乙酸乙酯和超纯水进行分液，有机相用无水MgSO4干燥，浓缩的有机相经硅胶漏斗及重结晶得到中间体4；
步骤5、化学式1所示化合物的制备
将中间体4、化合物3、碳酸钾加入到1,4-二氧六环/水的混合溶剂中，使用氮气置换空气三次，加入四(三苯基磷)钯，再次用氮气置换空气三次，在氮气保护下加热，TLC监测；待反应结束后，在氮气保护下冷却至室温；使用分液漏斗进行分液，保留有机相；使用硅藻土除去催化剂，用DCM洗硅藻土至无产品；浓缩滤液至少量，硅胶拌样，使用硅胶漏斗进行分离，得到化学式1所示化合物；
其合成路线如下：
Figure FDA0003700286860000061
式中，Hal为卤素，Ra、Rb、m、n、L1、L2、A、Ar与权利要求1中各化合物上的取代基团相对应。
3.一种包含权利要求1所述的蓝色荧光主体化合物的有机电致发光器件。
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