CN112979626B - 一种用于有机发光的化合物及其应用 - Google Patents
一种用于有机发光的化合物及其应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及热激活延迟荧光材料领域,尤其涉及一种用于有机发光的化合物 及其应用。
背景技术
有机发光二极管(OLED)由于具有驱动电压低、响应速度快、色彩丰富、 视角宽、可挠曲等诸多优点而受到了科学界和产业界的高度重视,并被誉为继液 晶显示后的新一代显示技术,具有巨大的潜在应用。
热激活延迟荧光(TADF)材料是继有机荧光材料和有机磷光材料之后发展 的第三代有机发光材料。该类材料一般具有小的单线态-三线态能级差(△EST), 三线态激子可以通过反系间窜越转变成单线态激子发光。这可以充分利用电激发 下形成的单线态激子和三线态激子,器件的内量子效率可以达到100%。同时, 材料结构可控,性质稳定,价格便宜无需贵重金属,在OLEDs领域的应用前景广阔。
目前大多数的TADF发光材料在稀溶液状态下都具有较高的发光量子产率, 发光很强,但在固体状态其发光则往往变得很弱甚至不发光,这是由于聚集导致 了发光的猝灭(ACQ)。在实际应用中OLED发光材料必须在固体薄膜状态下使 用,而随着TADF材料固体薄膜的形成,聚集发光猝灭效应却往往使之失去实用意义。由于AIE材料在固体状态的发光效率要远远高于溶液状态,故而能克服 发光材料的ACQ效应。
因此,把聚集诱导发光(AIE)性质和TADF性质相结合,开发出具有AIE 性质的TADF材料,将能解决TADF材料的ACQ问题,有望制备出成本低效率 高的非掺杂OLED。
发明内容
本发明的目的是针对现有技术中的不足,提供一种用于有机发光的化合物及 其应用。
为实现上述目的,本发明采取的技术方案是:
本发明的第一方面是提供一种用于有机发光的化合物,所述化合物的结构如 式(I)所示:
其中,Ar1和Ar2分别独立地选自氢或给电子结构单元,但Ar1和Ar2不同时 为氢。
优选地,所述给电子结构单元由二苯胺、咔唑、吩噻嗪和吩噁嗪中的任意两 种构成。
优选地,所述给电子结构单元选自:
优选地,所述化合物选自:
本发明的第二方面是提供一种有机电致发光材料,包括如上所述的化合物。
本发明的第三方面是提供一种发光层,包括如上所述的有机电致发光材料。
本发明的第四方面是提供一种有机电致发光器件,包括如上所述的发光层。
本发明采用以上技术方案,与现有技术相比,具有如下技术效果:
本发明用于有机发光的化合物具有聚集诱导发光性质,可以克服传统热激活 延迟荧光材料的聚集淬灭,可以获得优异的发光性能;制备工艺简单,纯化容易, 产率高;同时具有较高的热分解温度和玻璃化转变温度;通过使用特定位置连接 的二苯并硫氧六元杂环化作为吸电子基团,通过和不同的给电子基团相连,在保 持其高三线态能级的同时,具有优良的电荷传输性能,使其同时具备优异的空穴和电子传输性能,拓宽电荷复合区域,同时具备大的反向系间窜越速率,从而有 效利用激发三重态能量;本发明使用上述热激活延迟聚集诱导发光材料中的砜基 可以与附近氢原子形成氢键,避免了化合物键角的过度扭曲导致的键能削弱,可 维持更好的化学稳定性,同时在合成上具有明显优势,有利于材料的产业化应用; 所制备的非掺杂OLED器件,其发光层的发光亮度高和稳定性好,从而使得 OLED器件的发光效率和使用寿命都能达到实用化要求,具有良好的产业化前 景。
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作出创造性劳动的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。
需要说明的是,在不冲突的情况下,本发明中的实施例及实施例中的特征可 以相互组合。
下面结合具体实施例对本发明作进一步说明,但不作为本发明的限定。
实施例1
中间体A1
将原料A(l0mmol)加入100mL的二口瓶,加入30mL的醋酸,并加入3 倍量双氧水,升温至回流反应2小时;反应后冷却至室温,析出固体用乙醇和水 洗涤,经MgSO4干燥,过滤,浓缩并经柱层析(硅胶,从50:1PE/CH2Cl2至 3:1PE/CH2Cl2),得中间体A1(82%收率),为白色固体。
中间体A2
取4-溴二苯胺(10mmol)溶于20mL DMF(二甲基甲酰胺)中,搅拌下加 入叔丁醇钾(12mmol)并升温到60℃恒温30min,然后加入中间体A1(10mmol), 再升温到110℃反应12h;停止反应,冷却后倒入200mL水中产生沉淀,抽滤, 用水洗多次;把固体溶于100mL二氯甲烷中成溶液,加入适量无水硫酸钠干燥,过滤;滤液中加入200mL丙酮,利用旋转蒸发仪蒸出二氯甲烷和大部分的丙酮 得到沉淀,抽滤,用少量丙酮洗3次,真空烘干得白色粉末,得到中间体A2, 产率80%。
把中间体A2(2.50mmol)、吩噁嗪(3.75mmol)、K2CO3(7.49mmol)、1,10- 邻菲罗啉(0.10g)、18-冠醚-6(0.10g)、碘化亚铜(0.20g)和30mL DMF加入 250mL三口瓶中,在氩气保护下加热到170℃反应36h。反应液冷却至室温后倒 200mL冰盐水中,抽滤,固体用蒸馏水洗涤3次。粗产物以体积比为1:1的正己 烷和二氯甲烷混合溶液为洗脱液进行硅胶柱层析分离提纯,所得固体经真空干燥 后为白色粉末,质量为0.75g,产率为62%。
质谱m/z:580.17(计算值:580.15)。理论元素含量(%)C36H24SN2O4:C, 74.47;H,4.17;N,4.82;S,5.52;实测元素含量(%):C,74.40;H,4.11; N,4.79;S,5.48。上述结果证实获得产物为目标产品。
实施例2
合成方法与实施例1类似:
中间体B2
把中间体B2(2.50mmol)、吩噁嗪(14mmol)、K2CO3(10mmol)、1,10-邻 菲罗啉(0.20g)、18-冠醚-6(0.20g)、碘化亚铜(0.40g)和40mL DMF加入250mL 三口瓶中,在氩气保护下加热到170℃反应36h。反应液冷却至室温后倒200mL 冰盐水中,抽滤,固体用蒸馏水洗涤3次。粗产物以体积比为2:1的正己烷和二氯甲烷混合溶液为洗脱液进行硅胶柱层析分离提纯,所得固体经真空干燥后为白 色粉末,产率为62%。
质谱m/z:928.25(计算值:928.27)。理论元素含量(%)C60H40SN4O5:C, 77.57;H,4.34;N,6.03;S,3.45;实测元素含量(%):C,77.59;H,4.39; N,6.11;S,3.44。上述结果证实获得产物为目标产品。
实施例3:Ar1/Ar2的合成
取3-溴咔唑(12mmol)置于100mL圆底烧瓶中,加入50mL乙酸酐,同时 加入乙醚三氟化硼0.1mL,回流20min,可以看见析出大量白色固体,抽滤,干 燥后即可得到外观白色,似面粉的产品中间体1;产率98%。
把中间体1(2.50mmol)、咔唑(3.75mmol)、K2CO3(7.49mmol)、1,10-菲 罗啉(0.10g)、18-冠醚-6(0.10g)、碘化亚铜(0.20g)和30mL DMF加入250mL 三口瓶中,在氩气保护下加热到170℃反应36h。反应液冷却至室温后倒200mL 冰盐水中,抽滤,固体用蒸馏水洗涤3次。粗产物以体积比为6:1的正己烷和二氯甲烷混合溶液为洗脱液进行硅胶柱层析分离提纯,所得固体经真空干燥后为白 色粉末,所得产物为中间体2,产率为62%。
取中间体2(3.7mmol),KOH(35.7mmol),10mL THF,5mL DMSO和2mL 水置于100mL圆底烧瓶中;加热搅拌回流反应4h,TLC法检测反应进程;反应 完毕,蒸出把THF后倒入水中析出,抽滤,干燥即得到的粗产物用EtOH重结 晶,以少量活性炭脱色,最终得到白色的晶体为中间体3;产率为95%。
按上述方法,以类似的合成路线合成以下中间体:
实施例4
取中间体304(10mmol)溶于20mL DMF(二甲基甲酰胺)中,搅拌下加入 叔丁醇钾(12mmol)并升温到60℃恒温30min,然后加入中间体A1(10mmol), 再升温到110℃反应12h;停止反应,冷却后倒入200mL水中产生沉淀,抽滤, 用水洗多次;把固体溶于100mL二氯甲烷中成溶液,加入适量无水硫酸钠干燥, 过滤;滤液中加入200mL丙酮,利用旋转蒸发仪蒸出二氯甲烷和大部分的丙酮 得到沉淀,抽滤,用少量丙酮洗3次,浓缩并经柱层析(硅胶,从50:1PE/CH2Cl2至3:1PE/CH2Cl2),产物为白色固体,产率77%。
质谱m/z:594.15(计算值:594.11)。理论元素含量(%)C36H22S2N2O3:C,72.71;H,3.73;N,4.71;S,10.78;实测元素含量(%):C,72.74;H, 3.75;N,4.76;S,10.70。上述结果证实获得产物为目标产品。
实施例5
取中间体310(10mmol)溶于20mL DMF(二甲基甲酰胺)中,搅拌下加入 叔丁醇钾(12mmol)并升温到60℃恒温30min,然后加入中间体B1(10mmol), 再升温到110℃反应12h;停止反应,冷却后倒入200mL水中产生沉淀,抽滤, 用水洗多次;把固体溶于100mL二氯甲烷中成溶液,加入适量无水硫酸钠干燥, 过滤;滤液中加入200mL丙酮,利用旋转蒸发仪蒸出二氯甲烷和大部分的丙酮 得到沉淀,抽滤,用少量丙酮洗3次,浓缩并经柱层析(硅胶,从50:1PE/CH2Cl2至3:1PE/CH2Cl2),产物为白色固体,产率82%。
质谱m/z:928.24(计算值:928.27)。理论元素含量(%)C60H40SN4O5:C, 77.57;H,4.34;N,6.03;S,3.45;实测元素含量(%):C,77.52;H,4.37; N,6.05;S,3.49;。上述结果证实获得产物为目标产品。
实施例6
取中间体309(10mmol)溶于20mL DMF(二甲基甲酰胺)中,搅拌下加入 叔丁醇钾(12mmol)并升温到60℃恒温30min,然后加入中间体A1(10mmol), 再升温到110℃反应12h;停止反应,冷却后倒入200mL水中产生沉淀,抽滤, 用水洗多次;把固体溶于100mL二氯甲烷中成溶液,加入适量无水硫酸钠干燥, 过滤;滤液中加入200mL丙酮,利用旋转蒸发仪蒸出二氯甲烷和大部分的丙酮 得到沉淀,抽滤,用少量丙酮洗3次,浓缩并经柱层析(硅胶,从50:1PE/CH2Cl2至3:1PE/CH2Cl2)产物为白色固体,产率75%。
质谱m/z:578.28(计算值:578.13)。理论元素含量(%)C36H21SN2O4:C, 74.73;H,3.83;N,4.84;S,5.54;实测元素含量(%):C,74.77;H,3.88; N,4.90;S,5.61。上述结果证实获得产物为目标产品。
实施例7
取中间体305(10mmol)溶于20mLDMF(二甲基甲酰胺)中,搅拌下加入 叔丁醇钾(12mmol)并升温到60℃恒温30min,然后加入中间体B1(10mmol), 再升温到110℃反应12h;停止反应,冷却后倒入200mL水中产生沉淀,抽滤, 用水洗多次;把固体溶于100mL二氯甲烷中成溶液,加入适量无水硫酸钠干燥, 过滤;滤液中加入200mL丙酮,利用旋转蒸发仪蒸出二氯甲烷和大部分的丙酮得到沉淀,抽滤,用少量丙酮洗3次,浓缩并经柱层析(硅胶,从50:1PE/CH2Cl2至3:1PE/CH2Cl2),产物为白色固体,产率82%。
质谱m/z:956.11(计算值:956.19)。理论元素含量(%)C60H36S3N4O3: C,75.29;H,3.79;N,5.85;S,10.05;实测元素含量(%):C,75.22;H, 3.77;N,5.81;S,10.10。上述结果证实获得产物为目标产品。
对比例1(即化合物EM)
检测实施例1
对化合物1-5和对比例1进行了性能测试,主要考察了其热性能和发光性能, 其结果如表1所示。
表1
其中,Tg为玻璃化转变温度,通过差示扫描量热法(DSC,德国耐驰公司 DSC 204F1差示扫描量热仪)测定,升温速率10℃/min;热失重温度Td,1%是 在氮气气氛中失重1%时的温度,在日本岛津公司的TGA-50H热重分析仪上进 行测定,氮气流量为20mL/min;波长是利用日本岛津公司的RF-5301PC荧光分 光光度计测定的样品固体粉末的最大荧光发射波长;
应用实施例
本应用实施例提供一种有机电致发光器件,从下至上依次包括有透明基板 层、阳极层、空穴注入层、空穴传输层、发光层、电子传输层/空穴阻挡层、电 子注入层和阴极电极层。
具体的制作方法如下:
清洗透明玻璃基板层上的ITO阳极层,分别用去离子水、丙酮、乙醇超声 清洗各15分钟,然后在等离子体清洗器中处理2分钟;然后蒸镀HAT-CN,膜 厚10nm,该层为空穴注入层;接着,蒸镀NPB膜厚50nm,该层作为空穴传输 层;接着,蒸镀40nm的发光层;其中,主体材料如表2所示,GD-01作为掺杂 材料,掺杂质量浓度为6%;在发光层之上,通过真空蒸镀方式蒸镀TPBi,厚度 为35nm,这层有机材料作为空穴阻挡/电子传输层;在空穴阻挡/电子传输层之上, 真空蒸镀电子注入层LiF,厚度为1nm,该层为电子注入层;在电子注入层之上,真空蒸镀阴极Al(80nm),该层为阴极电极层。
表2
其中,器件测试性能以比较例1作为参照,电流效率均在10mA/cm2条件下 测得;寿命测试系统为Chroma的MODEL 58131OLED器件寿命测试仪。
所使用材料的具体结构如下:
从以上器件数据可以看出本发明化合物作为发光层主体材料可应用与 OLED发光器件制作,并且与对比元件1相比,无论是电流效率还是寿命均比已 知OLED材料获得较大改观,特别是器件的寿命获得较大的提升。
以上所述仅为本发明较佳的实施例,并非因此限制本发明的实施方式及保护 范围,对于本领域技术人员而言,应当能够意识到凡运用本发明说明书内容所作 出的等同替换和显而易见的变化所得到的方案,均应当包含在本发明的保护范围 内。
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