CN110903235B - 一种有机电致发光化合物及其制备方法与应用 - Google Patents

一种有机电致发光化合物及其制备方法与应用 Download PDF

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CN110903235B
CN110903235B CN201911236667.0A CN201911236667A CN110903235B CN 110903235 B CN110903235 B CN 110903235B CN 201911236667 A CN201911236667 A CN 201911236667A CN 110903235 B CN110903235 B CN 110903235B
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马晓宇
金成寿
汪康
孙向南
张雪
王钊
贺金新
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明公开了一种有机电致发光化合物及其制备方法与应用,所述有机电致发光化合物的结构通式如式

Description

一种有机电致发光化合物及其制备方法与应用
技术领域
本发明涉及有机发光材料技术领域,更具体的说是涉及一种有机电致发光化合物及其制备方法与应用。
背景技术
有机发光二极管(Organic Light-Emitting Diode,OLED)又称为有机电激光显示、有机发光半导体。由美籍华裔教授邓青云(Ching W.Tang)于1979年在实验室中发现。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。OLED显示技术具有自发光、广视角、几乎无穷高的对比度、较低耗电、极高反应速度等优点。但是,作为高端显示屏,价格上也会比液晶电视要贵。
OLED显示技术所具有得自发光特性,采用非常薄的有机材料涂层和玻璃基板,当有电流通过时,这些有机材料就会发光,而且OLED显示屏幕可视角度大,并且能够节省电能,从2003年开始这种显示设备在MP3播放器上得到了应用。从此以后逐渐进入人们的视野,成为研究的热点。
但是由于有机发光化合物的合成工艺比较复杂,耗时久,寿命低,针对当前OLED器件的产业应用要求,以及OLED器件的光电特性需求,必须选择更适合,具有高性能的电致发光材料,才能实现器件的高效率、长寿命和低电压的综合特性,因此,有机电致发光化合物的进一步开发迫在眉睫目前。
发明内容
有鉴于此,本发明提供了一种有机电致发光化合物及其制备方法与应用,本发明提供的有机电致发光化合物,具有良好的热稳定性,制备方法简单,含有该化合物的有机电致发光材料具有良好的发光效率和使用寿命。
为了实现上述目的,本发明采用如下技术方案:
一种有机电致发光化合物,所述有机电致发光化合物的结构通式如式I 所示:
Figure GDA0003907026520000021
其中:
Ar1、Ar2各自独立地表示取代或未取代的C1-C30烷基、取代或未取代的 C2-C30烯基、取代或未取代的C2-C30炔基、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~C60芳烷基胺基、取代或未取代的C6~C60杂芳基胺基、取代或未取代的C6~C60芳基胺基;所述Ar1、Ar2不成环,或连接形成C3-C30脂肪族环/芳香族环,其碳原子可置换为至少一个选自氮、氧和硫的杂原子,Ar1、Ar2相同或不同;
R1、R2、R3各自独立地表示氢、氘、卤素、腈基、硝基、羟基、取代或未取代的C1-C30烷基、取代或未取代的C2-C30烯基、取代或未取代的C2-C30炔基、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~C60芳烷基胺基、取代或未取代的C6~C60芳基胺基、取代或未取代的C6~C60杂芳基胺基;所述R1、R2、R3不成环,或与各自相邻的环连接形成C3-C30脂肪族环/芳香族环,其碳原子可置换至少一个选自氮、氧或硫原杂原子,R1、R2、R3相同或不同;
L独立地表示取代或未取代的C6-C30芳基、取代或未取代的C6-C30杂芳基;
X、Y各自独立地表示-O-、-S-、-SO2-、-C(R4)(R5)-、-N(R6)-、-Si(R7)(R8)-、 -Sn(R9)(R10)-和-Ge(R11)(R12)-,X、Y相同或不同;
R4~R12各自独立地表示取代或未取代的C1~C60烷基、取代或未取代的 C3~C60环烷基、取代或未取代的C6~C60芳基、取代或未取代的C6~C60杂芳基,R4~R12相同或不同;
G、Q、P独立地表示C6~C60芳基环、C6~C60的杂芳基环、C3~C30的脂肪族环,并且其碳原子可置换为至少一个选自氮、氧和硫的杂原子;G、Q、P 至少存在一个。
优选的,Ar1、Ar2各自独立地表示取代或未取代的C6-C30芳基、取代或未取代的C6-C30杂芳基、取代或未取代的C6~C60芳烷基胺基、取代或未取代的C6~C60杂芳基胺基、取代或未取代的C6~C60芳基胺基;所述Ar1、Ar2不成环,或连接形成咔唑/吖啶/吩噁嗪/吩噻嗪,Ar1、Ar2相同或不同。
优选的,R1、R2、R3各自独立地表示氢、氘、卤素、腈基、硝基、羟基、取代或未取代的C1-C30烷基、取代或未取代的C2-C30烯基、取代或未取代的 C2-C30炔基、取代或未取代的C6-C30芳基,所述R1、R2、R3不成环,或与各自相邻的环形成含N、O或S的五元环/六元环,R1、R2、R3相同或不同。
优选的,所述L独立地表示取代或未取代的C6-C30芳基。
优选的,所述X、Y各自独立地表示-O-、-S-、-SO2-、-C(R4)(R5)-、-N(R6)-, X、Y相同或不同;R4~R5各自独立地表示C1~C60烷基、C3~C60环烷基、C6~C60芳基、C6~C60杂芳基,R4~R5相同或不同。
优选的,所述有机发光化合物表示为[化学式2]-[化学式7]所示:
Figure GDA0003907026520000041
优选的,所述有机电致发光化合物的具体结构式为:
Figure GDA0003907026520000051
Figure GDA0003907026520000061
Figure GDA0003907026520000071
Figure GDA0003907026520000081
本发明还提供了所述的有机电致发光化合物的制备方法,包括如下步骤:
所述制备方法的合成路线为:
Figure GDA0003907026520000091
S1、将下述通式I-1的化合物、下述通式I-2的化合物、碳酸钾、四三苯基磷钯依次加入到体积比为3:1:1的甲苯/乙醇/水的混合溶剂中,其中,所述通式I-1的化合物与所述下述通式I-2的化合物的摩尔比为1:(1-1.2),接着在惰性气体保护下,在温度为95-105℃的条件下,回流搅拌至反应结束,经过后处理得到下述通式I-3的化合物;
S2、将下述通式I-3的化合物加入到三环己基膦中,在温度120-130℃的条件下,反应6-8h,反应结束后,经过后处理得到下述通式I-4的化合物;
S3、将下述通式I-4的化合物、下述通式I-5的化合物加入到甲苯中,其中,所述通式I-4的化合物与所述通式I-5的化合物的摩尔比为20:(20-21),在惰性气体保护下,依次加入三叔丁基磷、叔丁醇钠,在温度为110-111℃,速率为200-240rpm/min的条件下,回流搅拌至反应结束,经过后处理得到所述式I-6的目标化合物;
S4、将下述通式I-6的化合物、下述通式I-7的化合物加入到甲苯中,在惰性气体保护下,依次加入双钯、三叔丁基磷、叔丁醇钠,在温度为110-111℃,速率为200-240rpm/min的条件下,回流搅拌至反应结束,经过后处理得到所述式I的目标化合物;
Figure GDA0003907026520000101
优选的,所述通式I-6的化合物与所述通式I-7的化合物的摩尔比为 (20-24):(21-26)。
优选的,所述步骤S1中,后处理过程为:反应结束常温下,分液,水相使用二氯甲烷萃取,合并有机相,浓缩产品溶液,用二氯甲烷和石油醚析出,过滤得到所述通式I-3的化合物。
优选的,所述步骤S2中,后处理过程为:常温下,缓慢加入水,搅拌析出固体,过滤干燥,得到所述通式I-4的化合物。
优选的,所述步骤S3中,后处理过程为:常温下,加入水和二氯甲烷萃取,浓缩产品溶液,用二氯甲烷和石油醚析出,过滤得到所述通式I-6的化合物。
优选的,所述步骤S4中,后处理过程为:常温下,加入水和二氯甲烷萃取,有机层浓缩拌硅胶,柱层析(DCM:PE=1:7)得到所述通式I的目标化合物。
本发明进一步提供了一种有机电致发光器件,包括基板,以及依次蒸镀在基板上的阳极层、空穴注入层、空穴传输层、有机发光层、电子传输层、电子注入层和阴极层,所述有机发光层包括主体材料和掺杂材料,所述掺杂材料为式I 所述的有机电致发光化合物。
优选的,所述主体物质和所述掺杂材料的重量比为(97-99):(3:1),所述有机发光层的厚度为20-40nm。
本发明还进一步提供了上述有机电致发光器件在发光器件、太阳电池、电子纸、感光体或薄膜晶体管中的应用。
经由上述的技术方案可知,与现有技术相比,本发明提供了一种有机电致发光化合物、其制备方法及包含该发光化合物的有机电致发光器件,具有如下有益效果:
(1)本发明提供的有机电致发光化合物,具有良好的热稳定性,含有该化合物的有机电致发光器件具有良好的发光效率和使用寿命,利用本发明提供的有机电致发光化合物用作空穴传输层时,其寿命及效率与对比材料高近2 倍,而驱动电压仅是对比材料的1/2左右。
(2)本发明提供的有机电致发光化合物的制备方法,工艺简单高效,制备的产物纯度高。
具体实施方式
下面将对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,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,都属于本发明保护的范围。
本发明提供了一种有机电致发光化合物,所述有机电致发光化合物的结构通式如式I所示:
Figure GDA0003907026520000121
其中:
Ar1、Ar2各自独立地表示取代或未取代的C1-C30烷基、取代或未取代的 C2-C30烯基、取代或未取代的C2-C30炔基、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~C60芳烷基胺基、取代或未取代的C6~C60杂芳基胺基、取代或未取代的C6~C60芳基胺基;所述Ar1、Ar2不成环,或连接形成C3-C30脂肪族环/芳香族环,其碳原子可置换为至少一个选自氮、氧和硫的杂原子,Ar1、Ar2相同或不同;
R1、R2、R3各自独立地表示氢、氘、卤素、腈基、硝基、羟基、取代或未取代的C1-C30烷基、取代或未取代的C2-C30烯基、取代或未取代的C2-C30炔基、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~C60芳烷基胺基、取代或未取代的C6~C60芳基胺基、取代或未取代的C6~C60杂芳基胺基;所述R1、R2、R3不成环,或与各自相邻的环连接形成C3-C30脂肪族或芳香族环,其碳原子可置换至少一个选自氮、氧或硫原杂原子,R1、R2、R3相同或不同;
L独立地表示取代或未取代的C6-C30芳基、取代或未取代的C6-C30杂芳基;
X、Y各自独立地表示-O-、-S-、-SO2-、-C(R4)(R5)-、-N(R6)-、-Si(R7)(R8)-、 -Sn(R9)(R10)-和-Ge(R11)(R12)-,X、Y相同或不同;
R4~R12各自独立地表示取代或未取代的C1~C60烷基、取代或未取代的 C3~C60环烷基、取代或未取代的C6~C60芳基、取代或未取代的C6~C60杂芳基, R4~R12相同或不同;
G、Q、P独立地表示C6~C60芳基环、C6~C60的杂芳基环、C3~C30的脂肪族环,并且其碳原子可置换为至少一个选自氮、氧和硫的杂原子;G、Q、P 至少存在一个。
实施例1
化合物1的合成,结构如下所示:
Figure GDA0003907026520000131
S1:中间体化合物1-3的制备
Figure GDA0003907026520000132
将50mmol中间体1-1、60mmol邻硝基苯硼酸(中间体1-2)、150mmol 碳酸钾、1mmol四三苯基磷钯,加入到300ml甲苯/乙醇/水的混合溶剂(体积比为3:1:1)中,氮气保护下升温至回流搅拌。反应结束常温下,分液,水相使用二氯甲烷萃取,合并有机相,浓缩产品溶液,用二氯甲烷和石油醚析出,过滤得中间体1-3,得到产品18.2g,收率80%,MW:455.02。
S2:中间体化合物1-4的制备
Figure GDA0003907026520000141
将40mmol中间体1-3,加入到50ml三环己基膦中,升温至120℃搅拌6h。反应结束,常温下,缓慢加入水,搅拌析出固体,过滤干燥,得到中间体1-4,得到产品16.29g,收率77%,MW:423.15。
S3:中间体化合物1-6的制备
Figure GDA0003907026520000142
将30mmol化合物1-4溶于150ml甲苯中,加入30mmol中间体1-5,氮气保护下加入双钯0.3mmol,三叔丁基膦3mmol,叔丁醇钠90mmol,升温至回流搅拌。反应结束常温下,加入水和二氯甲烷萃取,浓缩产品溶液,用二氯甲烷和石油醚析出,过滤得中间体1-6,得到产品13.85g,收率:80%, MW:577.74。
S4:化合物1的制备
Figure GDA0003907026520000143
将24mmol化合物1-6溶于150ml甲苯中,加入26mmol二苯基胺(中间体1-7),氮气保护下加入双钯0.25mmol,三叔丁基膦2.5mmol,叔丁醇钠 72mmol,升温至回流搅拌。反应结束常温下,加入水和二氯甲烷萃取,有机层浓缩拌硅胶,柱层析(DCM:PE=1:7)得化合物1,得到产品13.11g,收率 82%,MW:666.54。
实施例2~14
按照实施例1中步骤S1的中间体1-3的制备方法,以及反应摩尔用量,仅将相应反应物替换,可以合成实施例2~14的I-3中间体,其具体结构、产物质量、收率和FD-MS的结果如表1所示。
表1实施例2~14的I-3中间体的具体结构、产物质量、收率和FD-MS 的结果
Figure GDA0003907026520000151
Figure GDA0003907026520000161
按照实施例1中步骤S2的中间体1-4的制备方法,以及反应摩尔用量,仅将相应反应物替换,可以合成实施例2~14的I-4中间体,具体结构、产物质量、收率和FD-MS的结果如表2所示。
表2实施例2~14的I-4中间体的具体结构、产物质量、收率和FD-MS 的结果
Figure GDA0003907026520000162
Figure GDA0003907026520000171
Figure GDA0003907026520000181
按照实施例1中步骤S3的中间体1-6的制备方法,以及反应摩尔用量,仅将相应反应物替换,可以合成实施例2~14的I-6中间体,具体结构、产物质量、收率和FD-MS的结果如表3所示。
表3实施例2~14的I-6中间体的具体结构、产物质量、收率和FD-MS 的结果
Figure GDA0003907026520000182
Figure GDA0003907026520000191
按照实施例1中步骤S4的化合物1的制备方法,以及反应摩尔用量,仅将相应反应物替换,可以合成实施例2~14的目标化合物,具体结构、产物质量、收率和FD-MS的结果如表4所示.
表4实施例2~14的目标化合物的具体结构、产物质量、收率和FD-MS 的结果
Figure GDA0003907026520000201
Figure GDA0003907026520000211
实施例15
本实施例提供一种有机电致发光器件,包括包括基板、设于基板上的阳极层、设于阳极层上的空穴注入层、设于空穴注入层上的空穴传输层、设于空穴传输层上的有机发光层、设于有机发光层的电子传输层、设于电子传输层上的电子注入层和设置于电子注入层上的阴极层。
所述有机电致发光器件的制备方法包括如下步骤:
(1)将涂层厚度为
Figure GDA0003907026520000212
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,在洁净的环境下烘烤至完全干燥;
(2)把上述处理好的ITO玻璃基板置于蒸镀机,在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")作为空穴注入层,蒸镀膜厚为50nm;在上述空穴注入层膜上继续蒸镀空穴传输层,蒸镀膜厚为50nm;
(3)在空穴传输层上继续蒸镀一层上述的化合物1和4,4'-N,N'-联苯二咔唑("CBP")作为器件的发光层,其中,CBP为主体材料,本发明的化合物 1为掺杂材料,CBP和掺杂材料化合物1的重量比为97:3,蒸镀膜厚为40nm;
(4)在有机发光层上继续蒸镀Alq3作为电子传输层,蒸镀膜厚为60nm 厚度;在电子传输层上继续真空蒸镀LiF作为电子注入层,蒸镀膜厚为0.5nm;最后,在电子注入层上继续蒸镀Al作为阴极层,蒸镀膜厚为100nm,制备得到有机电致发光器件。
实施例16
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物5,制备得到有机电致发光器件。
实施例17
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物10,制备得到有机电致发光器件。
实施例18
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物15,制备得到有机电致发光器件。
实施例19
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物17,制备得到有机电致发光器件。
实施例20
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物25,制备得到有机电致发光器件。
实施例21
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物28,制备得到有机电致发光器件。
实施例22
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物30,制备得到有机电致发光器件。
实施例23
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物35,制备得到有机电致发光器件。
实施例24
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物40,制备得到有机电致发光器件。
实施例25
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物43,制备得到有机电致发光器件。
实施例26
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物48,制备得到有机电致发光器件。
实施例27
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物52,制备得到有机电致发光器件。
实施例28
按照与上述实施例5相同的步骤,仅将步骤(3)所用化合物1替换为化合物59,制备得到有机电致发光器件。
对比例1
按照与上述实施例15相同的步骤,仅将步骤(3)所用化合物1替换为化合物NPB,制备得到有机电致发光器件,NPB结构如下所示:
Figure GDA0003907026520000241
为了进一步说明本发明提供的有机电致发光化合物的发光性能,对实施例15~实施例28以及对比例1中所得到有机电致发光器件的性能发光特性进行测试,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,发光亮度,发光效率。
表5实施例15~实施例2 8以及比较例1中有机电致发光器件检测结果
Figure GDA0003907026520000242
结论:由表1中性能测试结果可知,器件测试的亮度为2500cd/m2,本发明提供的有机电致发光器件可以应用于OLED发光器件,并且与对比例1相比,本发明提供的有机电致发光器件的驱动电压为3.1~3.7V,仅是对比例1 (驱动电压为6.4)的一半,寿命(123.8~145.2)以及效率(17.0~18.9)是对比例1(寿命:77.5,效率:8.0)的两倍左右,因此,与已知OLED材料相比,本发明提供的有机电致发光器件具有效率高、寿命长的特性,光学性能更加优异,具有显著的进步。
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。对于实施例公开的装置而言,由于其与实施例公开的方法相对应,所以描述的比较简单,相关之处参见方法部分说明即可。
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使用本发明。对这些实施例的多种修改对本领域的专业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,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要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 (6)

1.一种有机电致发光化合物,其特征在于,所述有机电致发光化合物的结构包括以下具体结构
Figure FDA0003907026510000011
Figure FDA0003907026510000021
2.一种根据权利要求1所述的有机电致发光化合物的制备方法,其特征在于,包括如下步骤:
S1、将下述通式I-1的化合物、下述通式I-2的化合物、碳酸钾、四三苯基磷钯依次加入到体积比为3:1:1的甲苯/乙醇/水的混合溶剂中,其中,所述通式I-1的化合物与所述下述通式I-2的化合物的摩尔比为1:(1-1.2),接着在惰性气体保护下,在温度为95-105℃的条件下,回流搅拌至反应结束,经过后处理得到下述通式I-3的化合物;
S2、将下述通式I-3的化合物加入到三环己基膦中,在温度120-130℃的条件下,反应6-8h,反应结束后,经过后处理得到下述通式I-4的化合物;
S3、将下述通式I-4的化合物、下述通式I-5的化合物加入到甲苯中,其中,所述通式I-4的化合物与所述通式I-5的化合物的摩尔比为20:(20-21),在惰性气体保护下,依次加入三叔丁基磷、叔丁醇钠,在温度为110-111℃,速率为200-240rpm/min的条件下,回流搅拌至反应结束,经过后处理得到所述式I-6的目标化合物;
S4、将下述通式I-6的化合物、下述通式I-7的化合物加入到甲苯中,在惰性气体保护下,依次加入双钯、三叔丁基磷、叔丁醇钠,在温度为110-111℃,速率为200-240rpm/min的条件下,回流搅拌至反应结束,经过后处理得到所述式I的目标化合物;
Figure FDA0003907026510000031
上述式中Ar1、Ar2、R1~R3、L、G、Q、P、X、Y与权利要求1所述化合物 中相同部分表示一致。
3.根据权利要求2所述有机电致发光化合物的制备方法,其特征在于,所述通式I-6的化合物与所述通式I-7的化合物的摩尔比为(20-24):(21-26)。
4.一种有机电致发光器件,包括基板,以及依次蒸镀在基板上的阳极层、空穴注入层、空穴传输层、有机发光层、电子传输层、电子注入层和阴极层,其特征在于,所述有机发光层包括主体材料和掺杂材料,所述掺杂材料为权利要求1所述的有机电致发光化合物。
5.根据权利要求4所述的一种有机电致发光器件,其特征在于,所述主体材料和所述掺杂材料的重量比为(97-99):(3-1),所述有机发光层的厚度为20-40nm。
6.一种有机电致发光器件的应用,其特征在于,所述应用为 权利要求4或5所述的有机电致发光器件在发光器件、太阳能 电池、电子纸、感光体或薄膜晶体管中的应用。
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