CN112457278B - 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 PDFInfo
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- CN112457278B CN112457278B CN202011331372.4A CN202011331372A CN112457278B CN 112457278 B CN112457278 B CN 112457278B CN 202011331372 A CN202011331372 A CN 202011331372A CN 112457278 B CN112457278 B CN 112457278B
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明公开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为
Description
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
信息时代的到来,现代人们的生活水平发生了日新月异的变化,对显示技术的要求也在不断的提高,作为下一代明星显示技术,OLED技术具有对比度高、柔性化、可视角广、响应快等优点。这使得OLED技术具有了良好的替代传统显示技术的潜力。目前中小尺寸的OLED显示屏已经在华为、小米、三星等公司出品的高端智能手机上得到了大规模的应用,市场反馈效果良好。
OLED发光器件犹如三明治的结构,空穴注入层、空穴传输层、发光层、电子传输层和电子注入层等结构组成。空穴传输层(HTL)负责调节空穴的注入速度和注入量,空穴传输材料直接影响OLED的效率和寿命。现有空穴传输区域中常用的化合物包括酞菁铜(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在使量子效率和使用寿命方面存在问题。这是因为空穴传输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。
另外,对于不同结构的OLED器件搭配而言,所使用的光电功能材料具有较强的选择性,相同的材料在不同结构器件中的性能表现,也可能完全迥异。因此,针对当前OLED器件的产业应用要求,以及OLED器件的不同功能膜层,器件的光电特性需求,必须选择更适合,具有高性能的OLED功能材料或材料组合,才能实现器件的高效率、长寿命和低电压的综合特性。
但是,目前公开的有机电致发光化合物,其发光效率和寿命均有一定不足。因此,开发一种发光效率高且寿命较好和低电压的材料是目前需要解决的技术问题。
发明内容
有鉴于此,本发明的目的在于提供了一种有机电致发光化合物及其制备方法与应用,母核引入的萘并呋喃使化合物整体的空间位阻增大,不对称的特定空间结构有利于减小分子间的凝聚力,减少结晶可能性,提高玻璃化转变温度,芳胺侧链基团是给电子基团,具有良好的空穴传输特性,即较高的空穴迁移率。该化合物在有机电致发光器件上的应用,使用该有机电致发光化合物制备的有机电致发光器件,具有较高的电流效率、低的驱动电压、较长的磷光寿命。
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如式I所示:
其中:
a,b独立地选自0或1,且a,b不能同时为0;
X为化学键,或X独立地选自O、S、Si(R5R6)、C(R7R8)或NR9;
R1-R4的位置分别为所在苯环的任意位置,且R1-R4的个数为0~4;
R1-R9独立地选自氢、氘、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(3元-30元)环烷基、取代或未取代的(3元-30元)杂环烷基、取代或未取代的(C6-C30)芳基、取代或未取代的(3元-30元)杂芳基、取代或未取代的(3到30元)杂芳基胺基、取代或未取代的(C6~C60)芳基胺基、取代或未取代的(C1-C30)烷氧基、取代或未取代的(C6-C60)芳氧基,
或与相邻取代基连接形成单环或多环(C3-C30)脂肪族环或(3元到30元)芳香族环,且其至少一个碳原子置换为杂原子氮、氧或硫;
Ar1-Ar4独立地表示取代或未取代的(C6-C30)芳基、取代或未取代的(3元到30元)杂芳基、取代或未取代的(C10-C30)稠环基、取代或未取代的(3到30元)杂芳基胺基、取代或未取代的(C6~C60)芳基胺基、取代或未取代的(C10-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,且至少一个碳原子置换为杂原子氮、氧、硫或硅。
优选地,R1-R9独立地选自甲基、乙基、丙基、叔丁基、烷氧基、烷巯基、芳氧基、苯基、联苯基、萘基、二甲基芴基,二苯基芴基或螺环基。
优选地,Ar1-Ar4独立地选自萘基、蒽基、菲基、苯并菲,苯基、咔唑基、叔丁基苯基、甲基苯基、三联苯基、联苯基、二苯并呋喃基、二苯并噻吩基、芴基、螺基及其衍生物。
优选地,所述取代的取代基至少一个选自卤素、腈基、羟基、羰基、酯基、甲硅烷基、硼基、烷基、环烷基、环氧基、烯基、烷基胺基、杂环基胺基、芳基胺基、芳基或杂环基。
优选地,所述R1~R9中的氢原子被氘代;所述Ar1-Ar4中的氢原子被氘代。
优选地,所述有机电致发光化合物选自下述结构中的任意一个:
本发明还提供了一种所述的有机电致发光化合物的制备方法,当a=1,b=0时,有机电致发光化合物的结构式II所示;当a=1,b=1时,有机电致发光化合物的结构式III所示;当a=0,b=1时,有机电致发光化合物的结构式IV所示;
其中,式II、式III及式IV化合物的合成路线分别如下:
式II、式III及式IV化合物的制备方法均包括以下步骤:
S1、将M溶于四氢呋喃,在氮气氛围下,将反应体系降温至-70~-78℃,加入n-BuLi,并搅拌2-4h,在将溶于四氢呋喃的N,加入反应体系,再升温至室温搅拌10-12h,加入蒸馏水中止反应,经过后处理后得到K;
S2、在K中加入冰醋酸,加热至110-120℃,缓慢滴加浓硫酸,浓硫酸的体积是中间体摩尔数的0.1-0.2倍,滴加时间5-10分钟,搅拌5-20min,冷却至室温,加入碳酸氢钠溶液终止反应,经后处理后得到式II、式III或式IV化合物;
且根据式II、式III及式IV化合物的合成路线,M代表反应物A或反应物D,N代表反应物B或反应物C,所述K代表中间体II、中间体III或中间体IV。
更具体地说,式II化合物的合成路线如下:
式II化合物的制备方法包括以下步骤:
S1、将反应物A溶于四氢呋喃,在氮气氛围下,将反应体系降温至-75~-78℃,加入n-BuLi,并搅拌2-4h,在将溶于四氢呋喃的反应物B,加入反应体系,再升温至室温搅拌10-12h,加入蒸馏水中止反应,经过后处理后得到中间体II;
所述后处理的操作为:分液收集有机相,加入无水硫酸镁干燥。除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂,得到固体有机物。浓缩结束后向其中加入乙酸乙酯和乙醇加热至75-85℃回流,搅拌3-6h,抽滤得到固体,滤饼用石油醚淋洗,放入65-75℃烘箱中烘干8-12h;
S2、在中间体II中加入冰醋酸,加热至115-120℃,缓慢滴加浓硫酸,浓硫酸的体积是中间体摩尔数的0.1-0.2倍,滴加时间5-10分钟,搅拌5-10min,冷却至室温,加入碳酸氢钠溶液终止反应,经后处理后得到式II化合物;
所述后处理的操作为:分液水相用二氯甲烷萃取三次,收集有机相,加入无水硫酸镁干燥,除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂得到固体有机物,加入甲苯中重结晶,过滤,将滤饼用150-300mL石油醚淋洗,放入80-85℃烘箱干燥12-15h;
式III化合物的合成路线如下:
式III化合物的制备方法与式II的合成步骤相同,不同之处在于将反应物B换成反应物C,将中间体II换成中间体III;
式IV化合物的合成路线如下:
式IV化合物的制备方法与式II的合成步骤相同,不同之处在于将反应物A和反应物B换成反应物C和反应物D,将中间体II换成中间体IV。
优选地,所述化合物A、n-BuLi和化合物B的摩尔比为1:(1.1-1.2):(1.1-1.2);
所述化合物A、n-BuLi和化合物C的摩尔比为1:(1.1-1.2):(1.1-1.2);
所述化合物D、n-BuLi和化合物C的摩尔比为1:(1.1-1.2):(1.1-1.2)。
优选地,所述反应物A的合成:将原料A和原料B溶于干燥甲苯后,在氮气氛围下,加入Pd2(dba)3、P(t-Bu)3、t-BuONa;升温到110-120℃,并且搅拌混合物10-15h,经后处理后得到反应物A,其结构如下所示;
所述原料A、原料B、Pd2(dba)3、P(t-Bu)3、t-BuONa的反应摩尔比为(1-1.2):(1-1.2):(0.011-0.015):(0.05-0.1):(2.0-3.0);
所述后处理的操作为:使用硅藻土趁热抽滤,滤液冷却至室温,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,置于1,4-二氧六环中,升温至100-120℃使固体有机物完全溶解,之后逐渐降低温度到大部分固体析出,过滤,将滤饼用150mL-300mL石油醚淋洗,放入65-75℃烘箱干燥12-18h;
所述反应物C的合成:将原料C和原料D溶于干燥甲苯后,在氮气氛围下,加入Pd2(dba)3、P(t-Bu)3、t-BuONa;升温到110-120℃,并且搅拌混合物10-15h,经后处理后得到反应物A,其结构如下所示;
所述原料C、原料D、Pd2(dba)3、P(t-Bu)3、t-BuONa的反应摩尔比为(1-1.2):(1-1.2):(0.011-0.015):(0.05-0.1):(2.0-3.0);
所述后处理的操作为:使用硅藻土趁热抽滤,滤液冷却至室温,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,置于1,4-二氧六环中,升温至100-120℃使固体有机物完全溶解,之后逐渐降低温度到大部分固体析出,过滤,将滤饼用150mL-300mL石油醚淋洗,放入65-75℃烘箱干燥12-18h;
本发明还进一步提供了上述的有机电致发光化合物在有机电致发光器件中的应用。
本发明还提供一种包含上述有机电致发光化合物的有机电致发光器件。
一种有机电致发光器件,包括第一电极、第二电极和有机物层,所述有机物层位于所述第一电极和所述第二电极之间;所述有机物层至少包括一个,且至少一个所述有机物层包含所述的有机电致发光化合物;所述有机电致发光化合物是以单一形态或与其它物质混合存在于有机物层中。
优选的,所述有机物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的组合。
优选的,所述有机电致发光器件包括发光层,所述发光层含有上述有机电致发光化合物。
本发明进一步提供了上述有机电致发光器件在有机发光器件、有机太阳能电池、电子纸、有机感光体或有机薄膜晶体管中的应用。
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,具有如下有益效果:
(1)本发明提供了一种新型结构的有机电致发光化合物,母核引入的萘并呋喃使化合物整体的空间位阻增大,不对称的特定空间结构有利于减小分子间的凝聚力,减少结晶可能性,提高玻璃化转变温度,芳胺侧链基团是给电子基团,具有良好的空穴传输特性,即较高的空穴迁移率。
(2)有机电致发光化合物具有合适的HOMO值,使空穴有小的注入势垒,使用这种有机电致发光化合物制备的有机电致发光器件驱动电压大幅降低,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。
(3)本发明的发光化合物制备方法简单,合成路线较短,原料易得,得到的粗品容易提纯,可得到高纯度的空穴传输材料,适合工业化生产。
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。
本发明实施例中,反应物A和反应物C的合成方法如下:
反应物A的合成:将原料A和原料B溶于干燥甲苯后,在氮气氛围下,加入Pd2(dba)3、P(t-Bu)3、t-BuONa;升温到110-120℃,并且搅拌混合物10-15h,使用硅藻土趁热抽滤,滤液冷却至室温,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,置于1,4-二氧六环中,升温至100-120℃使固体有机物完全溶解,之后逐渐降低温度到大部分固体析出,过滤,将滤饼用石油醚淋洗,放入65-75℃烘箱干燥12-18h,得到反应物A,其结构如下所示;其中,原料A、原料B、Pd2(dba)3、P(t-Bu)3、t-BuONa的反应摩尔比为(1-1.2):(1-1.2):(0.011-0.015):(0.05-0.1):(2.0-3.0)。
反应物C的合成:将原料C和原料D溶于干燥甲苯后,在氮气氛围下,加入Pd2(dba)3、P(t-Bu)3、t-BuONa;升温到110-120℃,并且搅拌混合物10-15h,使用硅藻土趁热抽滤,滤液冷却至室温,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,置于1,4-二氧六环中,升温至100-120℃使固体有机物完全溶解,之后逐渐降低温度到大部分固体析出,过滤,将滤饼用石油醚淋洗,放入65-75℃烘箱干燥12-18h,得到反应物A,其结构如下所示;其中原料C、原料D、Pd2(dba)3、P(t-Bu)3、t-BuONa的反应摩尔比为(1-1.2):(1-1.2):(0.011-0.015):(0.05-0.1):(2.0-3.0)。
实施例1
化合物1的合成,其具体的合成步骤如下:
(1)将反应物A-1(50mmol)加入到三口瓶中,加入200mL无水四氢呋喃,氮气置换三次,随后将反应体系降温至-78℃,滴加(2.5M)n-BuLi(55mmol),在-78℃下搅拌2h。将反应物B-1(55mmol)溶于四氢呋喃中,滴加至反应体系,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂,得到固体有机物。浓缩结束后向其中加入50mL乙酸乙酯和250mL乙醇加热至80℃回流,搅拌3h,抽滤得到固体,滤饼用150mL石油醚淋洗,放入65℃烘箱中烘干12h,得到中间体1(28.2g,Ms:725.53,产率:78%)。
(2)将中间体1(35mmol)加入三口瓶中,加入冰醋酸,加热至120℃,用滴定管缓慢滴加浓硫酸5mL,滴加时间10分钟,搅拌5min。冷却至室温,加入碳酸氢钠溶液终止反应,分液,水相用二氯甲烷萃取三次,收集有机相,加入无水硫酸镁干燥,除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂得到固体有机物,加入甲苯中,过滤,将滤饼用150mL石油醚淋洗,放入80℃烘箱干燥12h,得到化合物1(21.3g,Ms:707.79,产率:86%)。
对所得化合物1进行检测分析,结果如下:
质谱测试:理论值为707.92;测试值为707.79。
元素分析:
理论值:C,89.92;H,5.84;N,1.98;O,2.26;
测试值:C,89.89;H,5.88;N,1.99;O,2.24。
实施例2
化合物45的合成,其具体的合成步骤如下:
(1)将反应物A-45(50mmol)加入到三口瓶中,加入200mL无水四氢呋喃,氮气置换三次,随后将反应体系降温至-78℃,滴加(2.5M)n-BuLi(55mmol),在-78℃下搅拌2h。将反应物B-45(55mmol)溶于四氢呋喃中,滴加至反应体系,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂,得到固体有机物。浓缩结束后向其中加入50mL乙酸乙酯和250mL乙醇加热至80℃回流,搅拌3h,抽滤得到固体,滤饼用150mL石油醚淋洗,放入65℃烘箱中烘干12h,得到中间体45(25.5g,Ms:707.54,产率:72%)。
(2)将中间体45(35mmol)加入三口瓶中,加入175mL冰醋酸,加热至120℃,用滴定管缓慢滴加5mL浓硫酸,滴加时间10分钟,搅拌5min。冷却至室温,加入175mL碳酸氢钠溶液终止反应,分液,水相用175mL二氯甲烷萃取三次,收集有机相,加入无水硫酸镁干燥,除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂得到固体有机物,加入甲苯中重结晶,过滤,将滤饼用150mL石油醚淋洗,放入80℃烘箱干燥12h,得到化合物45(21.2g,Ms:689.56,产率:88%)。
对所得化合物45进行检测分析,结果如下:
质谱测试:理论值为689.90;测试值为689.56。
元素分析:
理论值:C,87.05;H,6.28;N,2.03;O,4.64;
测试值:C,87.10;H,6.26;N,2.01;O,4.62。
实施例3
化合物72的合成,其具体的合成步骤如下:
(1)将反应物D-72(50mmol)加入到三口瓶中,加入200mL无水四氢呋喃,氮气置换三次,随后将反应体系降温至-78℃,滴加(2.5M)n-BuLi(55mmol),在-78℃下搅拌2h。将反应物C-72(55mmol)溶于四氢呋喃中,滴加至反应体系,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂,得到固体有机物。浓缩结束后向其中加入50mL乙酸乙酯和250mL乙醇加热至80℃回流,搅拌3h,抽滤得到固体,滤饼用150mL石油醚淋洗,放入65℃烘箱中烘干12h,得到中间体72(28.2g,Ms:657.46,产率:74%)。
(2)将中间体72(35mmol)加入三口瓶中,加入175mL冰醋酸,加热至120℃,用滴定管缓慢滴加5mL浓硫酸,滴加时间10分钟,搅拌5min。冷却至室温,加入175mL碳酸氢钠溶液终止反应,分液,水相用175mL二氯甲烷萃取三次,收集有机相,加入无水硫酸镁干燥,除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂得到固体有机物,加入甲苯中重结晶,过滤,将滤饼用150mL石油醚淋洗,放入80℃烘箱干燥12h,得到化合物72(21.3g,Ms:639.45,产率:90%)。
对所得化合物72进行检测分析,结果如下:
质谱测试:理论值为639.26;测试值为639.45。
元素分析:
理论值:C,90.11;H,5.20;N,2.19;O,2.50;
测试值:C,90.18;H,5.16;N,2.20;O,2.48。
实施例4
化合物105的合成,其具体的合成步骤如下:
(1)将反应物A-105(50mmol)加入到三口瓶中,加入200mL无水四氢呋喃,氮气置换三次,随后将反应体系降温至-78℃,滴加(2.5M)n-BuLi(55mmol),在-78℃下搅拌2h。将反应物C-105(55mmol)溶于四氢呋喃中,滴加至反应体系,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂,得到固体有机物。浓缩结束后向其中加入50mL乙酸乙酯和250mL乙醇加热至80℃回流,搅拌3h,抽滤得到固体,滤饼用150mL石油醚淋洗,放入65℃烘箱中烘干12h,得到中间体105(28.2g,Ms:725.53,产率:78%)。
(2)将中间体105(35mmol)加入三口瓶中,加入175mL冰醋酸,加热至120℃,用滴定管缓慢滴加5mL浓硫酸,滴加时间10分钟,搅拌5min。冷却至室温,加入175mL碳酸氢钠溶液终止反应,分液,水相用175mL二氯甲烷萃取三次,收集有机相,加入无水硫酸镁干燥,除去剩余的水分,过滤除去无水硫酸镁,将有机相通过旋转蒸发仪除去溶剂得到固体有机物,加入甲苯中重结晶,过滤,将滤饼用150mL石油醚淋洗,放入80℃烘箱干燥12h,得到化合物105(21.3g,Ms:707.79,产率:86%)。
对所得化合物105进行检测分析,结果如下:
质谱测试:理论值为707.92;测试值为707.79。
元素分析:
理论值:C,89.92;H,5.84;N,1.98;O,2.26;
测试值:C,89.89;H,5.88;N,1.99;O,2.24。
实施例5至实施例22
参照实施例1至4的合成方法完成对化合物5,15,18,23,29,32,38,42,50,56,62,67,77,84,88,90,95,100的合成,质谱和分子式以及产率如表1。
表1:
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。
本发明提供了一种有机电致发光器件,包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层,至少一个有机化合物层包含本发明制备的有机电致发光化合物。
所述第一电极和第二电极之间设置包括空穴注入层、空穴传输层、发光辅助层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层的至少一层或多层。
第一电极作为阳极,阳极优选包含具有高逸出功的材料。例如Ag、Pt或Au。优选的阳极材料在此是导电混合金属氧化物。特别优选的是氧化锡铟(ITO)或氧化铟锌(IZO)。
电子阻挡层可以设置在空穴传输层与发光层之间。作为电子阻挡层,可以使用本领域中已知的材料,例如基于芳基胺的有机材料。
发光层的材料是一种通过分别接收来自空穴传输层和电子传输层的空穴和电子,并将所接收的空穴和电子结合而能发出可见光的材料。此外,发光层可以包含主体材料和掺杂材料;主体材料和掺杂材料的质量比为90-99.5:0.5-10;掺杂材料可以包括荧光掺杂和磷光掺杂。
发光层可以发射红色、绿色或蓝色的光,并且可以由磷光材料或荧光材料形成。发光材料是能够通过接收分别来自空穴传输层和电子传输层的空穴和电子并使空穴与电子结合而发出在可见光区域内的光的材料。
所述磷光掺杂材料的包括铱、铂等的金属络合物的磷光材料。例如,可以使用Ir(ppy)3等绿色磷光材料,FIrpic、FIr6等蓝色磷光材料和Btp2Ir(acac)等红色磷光材料。对于荧光掺杂材料,可以用现有技术中公知的具有电子传输作用的化合物。
空穴阻挡层材料,可以使用现有技术中公知的具有空穴阻挡作用的化合物,例如,浴铜灵(BCP)等菲咯啉衍生物、噁唑衍生物、三唑衍生物、三嗪衍生物等,但不限于此。
空穴传输层包括通式I所示的含有萘并呋喃的有机电致发光化合物。
电子注入层可以起到促进电子注入的作用。具有传输电子的能力,防止发光层中产生的激子迁移至空穴注入层。本发明中使用的电子注入材料包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等及其衍生物,金属配合物,含氮五元环衍生物等,但不限于此。
第二电极作为阴极,优选包含具有低逸出功的金属,包含多种金属例如碱土金属、碱金属、主族金属或镧系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm等)的金属合金或多层结构。羟基喹啉锂(Liq)也可用于此目的。该层的层厚度优选在0.5和5nm之间。
本发明所述的器件可以用于有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
以下是本发明的实施举例,下面实施例是为了帮助本发明理解而提供的,并不是将本发明的内容限定在这个范围。并且本发明的各实施例中具体没有列举化合物的制备方法是有关行业通常应用的方法,实施例中记载的方法,在制备其他化合物时,也可以参考。
为了更进一步的描述本发明,以下列举更具体的器件实施例。
[器件实施例1]:制造含有化合物1的有机电致发光器件
将本发明的化合物用作发光辅助层物质,按照通常的方法,制备有机电致发光元件。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30nm的HAT-CN作为空穴注入层;接着蒸镀60nm厚度的化合物1作为空穴传输层。上述空穴传输材料蒸镀结束后,制作OLED发光器件的发光层,其结构包括OLED发光层所使用CBP作为主体材料(比例为97%重量比),Ir(ppy)3作为掺杂材料,掺杂比例为3%重量比,发光层膜厚为40nm。
接着,在上述发光层上以10nm的厚度真空沉积BAlq来形成空穴阻挡层,在上述空穴阻挡层上以40nm的厚度真空沉积Alq3来形成电子输送层。然后,以0.2nm厚度的LiF来形成电子注入层,接着,以150nm的厚度沉积铝(Al)来形成阴极,由此,制备出有机电致发光元件。
器件结构:ITO/HAT-CN/化合物1/CBP:Ir(ppy)3/BAlq/Alq3/LiF/Al。
如上所述地完成OLED发光器件后,用公知的驱动电路将阳极和阴极连接起来,测量器件的电流效率以及器件的寿命。按照上述步骤完成电致发光器件的制作后,测量器件的驱动电压,发光效率和寿命。
相关材料的分子结构式如下所示:
[器件实施例2]-[器件实施例22]
将器件实施例1中的化合物1分别置换为化合物5,15,18,23,29,32,38,42,45,50,56,62,67,72,76,84,88,90,95,100,105其他方法相同,分别制作含有化合物有机电致发光器件实施例2-器件实施例22。
[器件比较例1]
按照器件实施例1相同的方法制备有机电致发光器件,空穴传输层化合物结构如下:
对上述制备的有机电致发光器件加以正向直流偏置电压,利用Photo Research公司的PR-650光度测量设备测定有机电致发光特性,亮度为8000cd/m2下利用McScience公司的寿命测定装置测定了T95的寿命。结果见表2。
表2:本发明器件实施例1~22以及器件对比例1-2的发光特性测试结果(亮度值为8000cd/m2)
与传统的空穴传输材料(比较化合物1),驱动电压下降1.3-1.8V,发光效率提升30.6-39.4%,器件寿命提高57-97h。器件性能均得到显著提升。
本发明化合物与结构相似的比较化合物2相比,二者的主要区别在于萘并呋喃的引入,母核引入的萘并呋喃使化合物整体的空间位阻增大,不对称的特定空间结构有利于减小分子间的凝聚力,减少结晶可能性,提高玻璃化转变温度。引入的芳胺侧链基团是给电子基团,具有良好的空穴传输特性,即较高的空穴迁移率;材料的化合物具有合适的HOMO值,使空穴有小的注入势垒,利用本发明的发光化合物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。
驱动电压降低0.9-1.4V,效率降低提高15.3-24.1%,寿命提高26-66h,玻璃态转变温度提高7-18℃。由上述表2的结果能确认使用本发明提供的化合物作为空穴传输材料制备的有机电致发光器件表现出高的发光效率及长寿命并降低驱动电压。综上所述,本发明公开的含有苯并呋喃的有机电致发光器件在母核引入的萘并呋喃使化合物整体的空间位阻增大,不对称的特定空间结构有利于减小分子间的凝聚力,减少结晶可能性,提高玻璃化转变温度。芳胺侧链基团是给电子基团,具有良好的空穴传输特性,即较高的空穴迁移率;材料的化合物具有合适的HOMO值,使空穴有小的注入势垒,利用本发明的发光化合物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。此外,本发明的发光化合物制备方法简单,合成路线较短,原料易得,得到的粗品容易提纯,可得到高纯度的空穴传输材料,适合工业化生产。
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 (7)
2.根据权利要求1所述的一种有机电致发光化合物,其特征在于,所述R1~R4中的氢原子被氘代;所述Ar1-Ar4中的氢原子被氘代。
3.一种权利要求1所述的有机电致发光化合物的制备方法,其特征在于,当a=1,b=0时,有机电致发光化合物的结构式II所示;当a=1,b=1时,有机电致发光化合物的结构式III所示;当a=0,b=1时,有机电致发光化合物的结构式IV所示;
其中,式II、式III及式IV化合物的合成路线分别如下:
式II、式III及式IV化合物的制备方法均包括以下步骤:
S1、将M溶于四氢呋喃,在氮气氛围下,将反应体系降温至-70~-78℃,加入n-BuLi,并搅拌2-4h,再将溶于四氢呋喃的N,加入反应体系,再升温至室温搅拌10-12h,加入蒸馏水中止反应,经过后处理后得到K;
S2、在K中加入冰醋酸,加热至110-120℃,滴加浓硫酸,搅拌5-20min,冷却至室温,加入碳酸氢钠溶液终止反应,经后处理后得到式II、式III或式IV化合物;
且根据式II、式III及式IV化合物的合成路线,M代表反应物A或反应物D,N代表反应物B或反应物C,所述K代表中间体II、中间体III或中间体IV。
4.根据权利要求3所述的有机电致发光化合物的制备方法,其特征在于,所述反应物M、n-BuLi和反应物N的摩尔比为1:(1.1-1.2):(1.1-1.2)。
5.根据权利要求3所述的有机电致发光化合物的制备方法,其特征在于,所述反应物A的合成:将原料A和原料B溶于干燥甲苯后,在氮气氛围下,加入Pd2(dba)3、P(t-Bu)3、t-BuONa;升温到110-120℃,并且搅拌混合物10-14h,经后处理后得到反应物A,其结构如下所示;
所述原料A、原料B、Pd2(dba)3、P(t-Bu)3、t-BuONa的摩尔比为1:(1-1.2):(0.011-0.015):(0.05-0.1):(2.0-3.0);
所述反应物C的合成:将原料C和原料D溶于干燥甲苯后,在氮气氛围下,加入Pd2(dba)3、P(t-Bu)3、t-BuONa;升温到110-130℃,并且搅拌混合物10-15h,经后处理后得到反应物C,其结构如下所示;
所述原料C、原料D、Pd2(dba)3、P(t-Bu)3、t-BuONa的反应摩尔比为1:(1-1.2):(0.011-0.015):(0.05-0.1):(2.0-3.0);
6.一种权利要求1~2任一项所述的有机电致发光化合物的应用,其特征在于,所述有机电致发光化合物在有机电致发光器件中的应用。
7.一种有机电致发光器件,其特征在于,包括第一电极、第二电极和有机物层,所述有机物层位于所述第一电极和所述第二电极之间;所述有机物层至少包括一个,且至少一个所述有机物层包含权利要求1~2任一项所述的有机电致发光化合物;所述有机电致发光化合物是以单一形态或与其它物质混合存在于有机物层中,所述有机物层为空穴传输层。
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