CN112080273B - 有机电致发光化合物及包含该化合物的有机电致发光器件 - Google Patents
有机电致发光化合物及包含该化合物的有机电致发光器件 Download PDFInfo
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- CN112080273B CN112080273B CN201910513283.2A CN201910513283A CN112080273B CN 112080273 B CN112080273 B CN 112080273B CN 201910513283 A CN201910513283 A CN 201910513283A CN 112080273 B CN112080273 B CN 112080273B
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- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 230000035939 shock Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 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及包含该化合物的有机电致发光器件,该有机电致发光化合物结构式如式I所示:
Description
技术领域
本发明属于有机电致发光材料技术领域,具体涉及一种有机电致发光化合物及包含该化合物的有机电致发光器件。
背景技术
有机电致发光器件(Organic Light-emitting Devices,OLED)具有既薄又轻、主动发光、宽视角、快速响应、能耗低、低温和抗震性能优异以及潜在的柔性设计等优点。OLED为全固态器件,无真空腔,无液态成分,所以不怕震动,使用方便,加上高分辨力、视角宽和工作温度范围宽等特点,在武器装备和恶劣环境领域将会得到广泛应用。此外,OLED还可作为显示领域的平面背光源和照明光源应用。因此,OLED具有良好的发展前景,目前在发光效率、发光寿命和生产成本方面还需要进一步改善,而影响OLED发光效率的最重要因素就是有机电致发光材料。
有机电致发光器件的工作原理是当施加电场时,有机电致发光器件内的有机电致发光材料通过正极注入的空穴和负极注入的电子的重新结合而发光。
尽管这些有机电致发光材料提供了良好发光特性,但其具有以下缺点:(1)由于其低玻璃化转变温度和不良热稳定性,因此其可能在高温沉积过程期间在真空中发生降解,并且装置的寿命降低。(2)有机电致发光装置的功率效率由[(π/电压)×电流效率]给出,并且功率效率与电压成反比。尽管包括磷光主体材料的有机电致发光装置提供了高于包括荧光材料的有机电致发光装置的电流效率(cd/A),但显著高的驱动电压是必需的。因此,在功率效率(lm/W)方面没有优势。(3)进一步,当这些材料用于有机电致发光装置中时,有机电致发光装置的工作寿命短,并且仍需要提高发光效率。
目前对于有机电致发光器件提高性能的研究包括:降低器件的驱动电压,提高器件的发光效率,提高器件的使用寿命等。为了实现有机电致发光器件性能的不断提升,不但需要有机电致发光器件的结构和制作工艺的创新,更需要有机电致光电功能材料的不断研究和创新,创制出更高性能的有机电致功能材料。
就当前有机电致发光产业的实际需求而言,目前有机电致发光材料的发展还远远不够,落后于面板制造企业的要求。
发明内容
发明目的:针对上述技术问题,本发明提供了一种有机电致发光化合物及包含该化合物的有机电致发光器件。
为了达到上述发明目的,本发明所采用的技术方案如下:
一种有机电致发光化合物,其结构式如下所示:
其中,L表示单键、取代或未取代的苯基、取代或为取代的联苯基、取代或未取代的萘基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的9,9-二甲基芴基、取代或未取代的9,9'-二苯基芴基、取代或未取代的咔唑基、取代或未取代的螺二芴基、取代或未取代的N-苯基咔唑基、取代或未取代的N-联苯基咔唑基;
优选的,L为:单键、苯基、联苯基、二苯并呋喃基、9,9-二甲基芴基、N-苯基咔唑基、N-联苯基咔唑基、9,9-二苯基芴基、螺二芴基。
R1、R2、R3、R4、R5独立地表示氢、取代或未取代的C6-C30芳基、取代或未取代的C4-C30杂芳基。
优选的,R1、R2、R3、R4、R5独立地表示苯基、甲苯基、联苯基、三联苯基、萘基、菲基、芴基、螺二芴基、9,9'-二甲基芴基、9,9'-二苯基芴基、氧芴基、二苯并噻吩基、呋喃基、噻吩基、蒽基、苯并蒽基、荧蒽基、吡啶基、嘧啶基、喹啉基、三嗪基、咔唑基;
且R1、R2、R3、R4、R5中的苯基、甲苯基、联苯基、三联苯基、萘基、菲基、芴基、螺二芴基、9,9'-二甲基芴基、9,9'-二苯基芴基、氧芴基、二苯并噻吩基、呋喃基、噻吩基、蒽基、苯并蒽基、荧蒽基、吡啶基、嘧啶基、喹啉基、三嗪基、咔唑基是未取代的或进一步被C1-5烷基、C6-C30芳基、C4-C30杂芳基中的一个或多个取代而成的基团。
进一步优选的,R1、R2、R3、R4、R5、R6中的苯基、甲苯基、联苯基、三联苯基、萘基、菲基、芴基、螺二芴基、9,9'-二甲基芴基、9,9'-二苯基芴基、氧芴基、二苯并噻吩基、呋喃基、噻吩基、蒽基、苯并蒽基、荧蒽基、吡啶基、嘧啶基、喹啉基、三嗪基、咔唑基是未取代的或进一步被甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、苯基、甲苯基、联苯基、三联苯基、萘基、菲基、芴基、螺二芴基、9,9'-二甲基芴基、9,9'-二苯基芴基、氧芴基、二苯并噻吩基、呋喃基、噻吩基、蒽基、苯并蒽基、荧蒽基、吡啶基、嘧啶基、喹啉基、三嗪基、咔唑基中的一个或多个取代基取代而成的基团。
更进一步优选的,所述有机电致发光化合物为下列结构式化合物中的任意一种:
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本发明还提供了一种上述有机电致发光化合物的制备方法,其制备方法包括如下步骤:
将结构通式为的化合物Ⅰ、/>的化合物Ⅱ和碳酸钠加入到乙二醇二胺醚和水的混合溶液中,搅拌混匀后再依次加入三(邻甲苯基)膦和乙酸钯(II),升温至回流反应15-20h后,将有机相分出,水洗后减压浓缩,再经过柱层析后得到所述有机电致发光化合物。反应式如下:
上述有机电致发光化合物在制备有机电致发光器件中的应用。
一种包含上述有机电致发光化合物的有机电致发光器件,所述有机电致发光器件为阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层以及阴极顺次堆积的构造;
其中,阳极和发光层之间还设置有电子阻隔层;
阴极和发光层之间还设置有空穴阻隔层;
阴极表面还设置有覆盖层;
进一步地,所述空穴传输层、电子阻隔层、空穴阻隔层、电子传输层、发光层或者覆盖层中的至少一层包含至少一种上述的有机电致发光化合物。
更进一步地,空穴传输层和/或电子阻隔层中包括至少一种上述有机电致发光化合物。
一种包含上述有机电致发光器件的有机电致发光显示设备。
本发明的有益效果:
本发明与对比文件相比,引入苯并芳香环结构,增大了材料分子的刚性及共轭效应,增加分子的热稳定性及发光效率,由于材料分子稳定性的增加,大大提高了材料的寿命并且扩展了该类材料的应用范围,以氧芴、硫芴、咔唑和苯并咔唑作为桥联,破坏了分子对称性,降低了结晶性,避免了分子间的聚集作用,具有良好的成膜性和优异的荧光量子效率,本发明有机电致发光化合物无论是作为发光层的绿色磷光主体材料,具有明显优异的器件表现,器件的效率,寿命及外量子效率均得到非常大的提高。
具体实施方式
实施例中未注明具体条件者,按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者,均为可以通过市售购买获得的常规产品。
实施例1:
化合物G2的合成方法如下:
将化合物1(100g,299.84g/mol,333.5mmol)、化合物2(1eq,50g,150g/mol,333.5mmol)、四硼酸钠(1.5eq,190.78g,381.37g/mol,500.25mmol)加入到THF(500g,化合物1的5倍质量)和水(300g,化合物1的3倍质量)中,搅拌混匀溶解后,再将双(三苯基膦)二氯化钯(II)(2%eq,4.68g,701.9g/mol,6.67mmol)和水合肼(3%eq,0.5g,50.06g/mol,10mmol)加入,氮气保护下升温至70℃,搅拌反应48h,冷却至室温后过滤,减压浓缩除去一定量THF后加乙酸乙酯,萃取后分液,有机相无水硫酸钠干燥后减压浓缩得到化合物3粗品,化合物3粗品再经过柱层析后得到化合物3纯品(72.58g,收率78%),MS(EI):279(M+)。
将化合物(70g,279g/mol,250mmol)加入到二氯甲烷中(700g,化合物3的10倍质量),搅拌溶解后降温至5℃,缓慢将三溴化硼(1eq,62.63g,250.52g/mol,250mmol)滴加进入,搅拌反应15h后,加水淬灭,分液,有机相无水硫酸钠干燥后减压浓缩得到化合物4粗品,化合物4粗品再经过柱层析后得到化合物4纯品(63.47g,收率95.8%),MS(EI):265(M+)。
将化合物4(60g,265g/mol,226.4mmol)加入到无水DMF(600g,化合物4的10倍质量)中,搅拌溶解后降温至5℃,将氢化钠(1.1eq,5.98g,24g/mol,249mmol)分多次加入后,搅拌30min,升温至100℃反应1h,冷却至室温后加入乙醇(300g,化合物4的5倍质量),减压浓缩后得到化合物5粗品,再经过柱层析后得到化合物5纯品(50.2g,收率90.5%),MS(EI):245(M+)。
将化合物6(45.3g,245.97g/mol,184.4mmol)加入到无水THF中,冷却到-78℃,加入正丁基锂(1.1eq,12.99g,64.05g/mol,202.84mmol)的正己烷溶液,在此温度下继续搅拌2h,将硼酸三甲酯(2eq,38.32g,103.91g/mol,368.8mmol)缓慢恢复室温后反应15h,再冷却到-78℃,加水淬灭后过滤,滤液加二氯甲烷萃取,分液后有机相无水硫酸钠干燥后减压浓缩得到化合物7粗品,化合物7粗品再经过柱层析后得到化合物7纯品(35.74g,收率92.3%),MS(EI):212(M+)。
将化合物7(35g,212g/mol,166.7mmol)、化合物8(1.0eq,35g,212g/mol,166.7mmol)和碳酸钠(2eq,35.34g,105.99g/mol,333.4mmol)加入到乙二醇二胺醚(700g,化合物7的20倍质量)和水(700g,化合物7的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,1.52g,304.37g/mol,5mmol)和乙酸钯(II)(0.5%eq,1.87g,224.51g/mol,8.3mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物9粗品,化合物9粗品再经过柱层析后得到化合物9纯品(48.97g,收率85.4%),MS(EI):344(M+)。
将化合物9(48g,344g/mol,139.5mmol)加入到乙酸(960g,化合物9的20倍质量)和浓硫酸(960g,化合物9的20倍质量),混匀后再将N-溴代琥珀酰亚胺(1.0eq,24.8g,177.98g/mol,139.5mmol)避光反应2h,反应液倒入冰水混合物中,快速搅拌,将洗出的固体滤出,得到化合物10粗品,化合物10粗品再经过柱层析后得到化合物10纯品(35.79g,收率60.8%),MS(EI):422(M+)。
将化合物10(35g,422g/mol,82.9mmol)、化合物11(1.1eq,37.66g,413g/mol,91.2mmol)和碳酸钠(2eq,17.57g,105.99g/mol,165.8mmol)加入到乙二醇二胺醚(700g,化合物10的20倍质量)和水(700g,化合物10的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.76g,304.37g/mol,2.49mmol)和乙酸钯(II)(0.5%eq,0.93g,224.51g/mol,4.1mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G2粗品,化合物G2粗品再经过柱层析后得到化合物G2纯品(35.72g,收率60.6%),MS(EI):711(M+)。
实施例2:
化合物G15的合成方法如下:
步骤1-4与实施例1基本相同,其余步骤如下:
将化合物7(20g,212g/mol,94.3mmol)、化合物12(1.0eq,25.18g,267g/mol,94.3mmol)和碳酸钠(2eq,19.8g,105.99g/mol,188.6mmol)加入到乙二醇二胺醚(400g,化合物7的20倍质量)和水(400g,化合物7的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.86g,304.37g/mol,2.82mmol)和乙酸钯(II)(0.5%eq,1.06g,224.51g/mol,4.72mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物13粗品,化合物13粗品再经过柱层析后得到化合物13纯品(32.62g,收率86.7%),MS(EI):399(M+)。
将化合物13(32g,399g/mol,80.2mmol)加入到乙酸(640g,化合物13的20倍质量)和浓硫酸(640g,化合物13的20倍质量),混匀后再将N-溴代琥珀酰亚胺(1.0eq,14.3g,177.98g/mol,80.2mmol)避光反应2h,反应液倒入冰水混合物中,快速搅拌,将洗出的固体滤出,得到化合物14粗品,化合物14粗品再经过柱层析后得到化合物14纯品(23.41g,收率61.2%),MS(EI):477(M+)
将化合物14(20g,477g/mol,41.9mmol)、化合物15(1.1eq,28.03g,608g/mol,46.1mmol)和碳酸钠(2eq,8.88g,105.99g/mol,83.8mmol)加入到乙二醇二胺醚(400g,化合物14的20倍质量)和水(400g,化合物14的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.38g,304.37g/mol,1.26mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G15粗品,化合物G15粗品再经过柱层析后得到化合物G15纯品(24.53g,收率60.9%),MS(EI):961(M+)。
实施例3:
化合物G40的合成方法如下:
步骤1-6与实施例1基本相同,其余步骤如下:
将化合物10(20g,422g/mol,47.4mmol)、化合物16(1.1eq,31.81g,654g/mol,52.1mmol)和碳酸钠(2eq,10.05g,105.99g/mol,94.8mmol)加入到乙二醇二胺醚(400g,化合物10的20倍质量)和水(400g,化合物10的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.38g,304.37g/mol,1.26mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G15粗品,化合物G15粗品再经过柱层析后得到化合物G15纯品(24.53g,收率60.9%),MS(EI):961(M+)。
实施例4:
化合物G57的合成方法如下:
步骤1-4与实施例1基本相同,其余步骤如下:
将化合物7(20g,212g/mol,94.3mmol)、化合物17(1.0eq,27.16g,288g/mol,94.3mmol)和碳酸钠(2eq,19.8g,105.99g/mol,188.6mmol)加入到乙二醇二胺醚(400g,化合物7的20倍质量)和水(400g,化合物7的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.86g,304.37g/mol,2.82mmol)和乙酸钯(II)(0.5%eq,1.06g,224.51g/mol,4.72mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物13粗品,化合物13粗品再经过柱层析后得到化合物13纯品(34.50g,收率87.1%),MS(EI):420(M+)。
将化合物18(34g,420g/mol,80.9mmol)加入到乙酸(680g,化合物18的20倍质量)和浓硫酸(680g,化合物13的20倍质量),混匀后再将N-溴代琥珀酰亚胺(1.0eq,14.4g,177.98g/mol,80.9mmol)避光反应2h,反应液倒入冰水混合物中,快速搅拌,将洗出的固体滤出,得到化合物19粗品,化合物19粗品再经过柱层析后得到化合物19纯品(24.41g,收率60.6%),MS(EI):498(M+)
将化合物19(20g,498g/mol,40.2mmol)、化合物20(1.1eq,29.54g,668g/mol,44.2mmol)和碳酸钠(2eq,8.52g,105.99g/mol,80.4mmol)加入到乙二醇二胺醚(400g,化合物19的20倍质量)和水(400g,化合物19的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.37g,304.37g/mol,1.21mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G57粗品,化合物G57粗品再经过柱层析后得到化合物G57纯品(25.64g,收率61.2%),MS(EI):1042(M+)。
实施例5:
化合物G69的合成方法如下:
步骤1-6与实施例4基本相同,其余步骤如下:
将化合物19(20g,498g/mol,40.2mmol)、化合物21(1.1eq,32.88g,744g/mol,44.2mmol)和碳酸钠(2eq,8.52g,105.99g/mol,80.4mmol)加入到乙二醇二胺醚(400g,化合物10的20倍质量)和水(400g,化合物14的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.37g,304.37g/mol,1.21mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G69粗品,化合物G69粗品再经过柱层析后得到化合物G69纯品(27.77g,收率61.8%),MS(EI):1118(M+)。
实施例6:
化合物G71的合成方法如下:
步骤1-4与实施例1基本相同,其余步骤如下:
将化合物7(20g,212g/mol,94.3mmol)、化合物22(1.0eq,17.73g,188g/mol,94.3mmol)和碳酸钠(2eq,19.8g,105.99g/mol,188.6mmol)加入到乙二醇二胺醚(400g,化合物7的20倍质量)和水(400g,化合物7的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.86g,304.37g/mol,2.82mmol)和乙酸钯(II)(0.5%eq,1.06g,224.51g/mol,4.72mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物23粗品,化合物23粗品再经过柱层析后得到化合物23纯品(26.19g,收率86.8%),MS(EI):320(M+)。
将化合物23(26g,320g/mol,81.3mmol)加入到乙酸(520g,化合物23的20倍质量)和浓硫酸(520g,化合物23的20倍质量),混匀后再将N-溴代琥珀酰亚胺(1.0eq,14.5g,177.98g/mol,81.3mmol)避光反应2h,反应液倒入冰水混合物中,快速搅拌,将洗出的固体滤出,得到化合物24粗品,化合物24粗品再经过柱层析后得到化合物24纯品(20.09g,收率62.1%),MS(EI):398(M+)
将化合物24(20g,398g/mol,50.3mmol)、化合物25(1.1eq,22.85g,413g/mol,55.3mmol)和碳酸钠(2eq,10.66g,105.99g/mol,100.6mmol)加入到乙二醇二胺醚(400g,化合物24的20倍质量)和水(400g,化合物24的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.46g,304.37g/mol,1.51mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G71粗品,化合物G71粗品再经过柱层析后得到化合物G71纯品(20.80g,收率60.2%),MS(EI):687(M+)。
实施例7:
化合物G105的合成方法如下:
步骤1-5与实施例6基本相同,其余步骤如下:
将化合物24(20g,398g/mol,50.3mmol)、化合物25(1.1eq,18.64g,337g/mol,55.3mmol)和碳酸钠(2eq,10.66g,105.99g/mol,100.6mmol)加入到乙二醇二胺醚(400g,化合物24的20倍质量)和水(400g,化合物24的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.46g,304.37g/mol,1.51mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G105粗品,化合物G105粗品再经过柱层析后得到化合物G105纯品(18.87g,收率61.4%),MS(EI):611(M+)。
实施例8:
化合物G110的合成方法如下:
步骤1-5与实施例2基本相同,其余步骤如下:
将化合物14(20g,477g/mol,41.9mmol)、化合物26(1.1eq,30.79g,668g/mol,46.1mmol)和碳酸钠(2eq,8.88g,105.99g/mol,83.8mmol)加入到乙二醇二胺醚(400g,化合物14的20倍质量)和水(400g,化合物14的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.38g,304.37g/mol,1.26mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G110粗品,化合物G110粗品再经过柱层析后得到化合物G110纯品(25.88g,收率60.5%),MS(EI):1021(M+)。
实施例9:
步骤1-4与实施例1基本相同,其余步骤如下:
将化合物7(20g,212g/mol,94.3mmol)、化合物27(1.0eq,10.56g,112g/mol,94.3mmol)和碳酸钠(2eq,19.8g,105.99g/mol,188.6mmol)加入到乙二醇二胺醚(400g,化合物7的20倍质量)和水(400g,化合物7的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.86g,304.37g/mol,2.82mmol)和乙酸钯(II)(0.5%eq,1.06g,224.51g/mol,4.72mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物28粗品,化合物28粗品再经过柱层析后得到化合物28纯品(20.18g,收率87.7%),MS(EI):244(M+)。
将化合物28(20g,244g/mol,82.0mmol)加入到乙酸(400g,化合物28的20倍质量)和浓硫酸(400g,化合物28的20倍质量),混匀后再将N-溴代琥珀酰亚胺(1.0eq,14.6,177.98g/mol,82.0mmol)避光反应2h,反应液倒入冰水混合物中,快速搅拌,将洗出的固体滤出,得到化合物29粗品,化合物29粗品再经过柱层析后得到化合物29纯品(16.58g,收率62.8%),MS(EI):322(M+)
将化合物29(20g,322g/mol,62.1mmol)、化合物30(1.1eq,20.97g,307g/mol,68.3mmol)和碳酸钠(2eq,13.16g,105.99g/mol,124.2mmol)加入到乙二醇二胺醚(400g,化合物24的20倍质量)和水(400g,化合物24的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.57g,304.37g/mol,1.86mmol)和乙酸钯(II)(0.5%eq,0.069g,224.51g/mol,0.31mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G120粗品,化合物G120粗品再经过柱层析后得到化合物G120纯品(20.75g,收率61.2%),MS(EI):549(M+)。
实施例10:
化合物G146的合成方法如下:
步骤1-5与实施例6基本相同,其余步骤如下:
将化合物24(20g,398g/mol,50.3mmol)、化合物31(1.1eq,23.61g,427g/mol,55.3mmol)和碳酸钠(2eq,10.66g,105.99g/mol,100.6mmol)加入到乙二醇二胺醚(400g,化合物24的20倍质量)和水(400g,化合物24的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.46g,304.37g/mol,1.51mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G146粗品,化合物G146粗品再经过柱层析后得到化合物G146纯品(21.72g,收率61.6%),MS(EI):701(M+)。
实施例11:
化合物G1的合成方法如下:
步骤1-6与实施例1基本相同,其余步骤如下:
将化合物14(20g,477g/mol,41.9mmol)、化合物15(1.1eq,19.04g,413g/mol,46.1mmol)和碳酸钠(2eq,8.88g,105.99g/mol,83.8mmol)加入到乙二醇二胺醚(400g,化合物14的20倍质量)和水(400g,化合物14的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.38g,304.37g/mol,1.26mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G1粗品,化合物G1粗品再经过柱层析后得到化合物G1纯品(21.02g,收率65.5%),MS(EI):766(M+)。
实施例12:
步骤1-6与实施例2基本相同,其余步骤如下:
将化合物14(20g,477g/mol,41.9mmol)、化合物32(1.1eq,23.19g,503.17g/mol,46.1mmol)和碳酸钠(2eq,8.88g,105.99g/mol,83.8mmol)加入到乙二醇二胺醚(400g,化合物14的20倍质量)和水(400g,化合物14的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.38g,304.37g/mol,1.26mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G182粗品,化合物G182粗品再经过柱层析后得到化合物G182纯品(26.11g,收率72.8%),MS(EI):856(M+)。
实施例13:
步骤1-6与实施例2基本相同,其余步骤如下:
将化合物14(20g,477g/mol,41.9mmol)、化合物33(1.1eq,19.05g,413.16g/mol,46.1mmol)和碳酸钠(2eq,8.88g,105.99g/mol,83.8mmol)加入到乙二醇二胺醚(400g,化合物14的20倍质量)和水(400g,化合物14的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.38g,304.37g/mol,1.26mmol)和乙酸钯(II)(0.5%eq,0.047g,224.51g/mol,0.2mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G189粗品,化合物G182粗品再经过柱层析后得到化合物G182纯品(22.53g,收率70.2%),MS(EI):766(M+)。
实施例14:
步骤1-4与实施例1基本相同,其余步骤如下:
将化合物7(10g,212g/mol,47.17mmol)、化合物34(1.0eq,16.18g,343g/mol,47.17mmol)和碳酸钠(2eq,9.99g,105.99g/mol,94.34mmol)加入到乙二醇二胺醚(200g,化合物7的20倍质量)和水(200g,化合物7的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.43g,304.37g/mol,1.42mmol)和乙酸钯(II)(0.5%eq,0.053g,224.51g/mol,0.23mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物35粗品,化合物35粗品再经过柱层析后得到化合物35纯品(19.76g,收率88.2%),MS(EI):475(M+)。
将化合物35(19g,475g/mol,40mmol)加入到乙酸(380g,化合物35的20倍质量)和浓硫酸(380g,化合物35的20倍质量),混匀后再将N-溴代琥珀酰亚胺(1.0eq,7.12g,177.98g/mol,40mmol)避光反应2h,反应液倒入冰水混合物中,快速搅拌,将洗出的固体滤出,得到化合物36粗品,化合物36粗品再经过柱层析后得到化合物36纯品(15.95g,收率72.1%),MS(EI):553(M+)。
将化合物36(15g,553g/mol,27.12mmol)、化合物37(1.1eq,12.33g,413.16g/mol,29.83mmol)和碳酸钠(2eq,5.75g,105.99g/mol,54.24mmol)加入到乙二醇二胺醚(300g,化合物36的20倍质量)和水(300g,化合物36的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.25g,304.37g/mol,0.81mmol)和乙酸钯(II)(0.5%eq,0.03g,224.51g/mol,0.14mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G189粗品,化合物G182粗品再经过柱层析后得到化合物G182纯品(17.10g,收率74.9%),MS(EI):842(M+)。
实施例15:
步骤1-4与实施例1基本相同,其余步骤如下:
将化合物7(10g,212g/mol,47.17mmol)、化合物38(1.0eq,16.18g,343g/mol,47.17mmol)和碳酸钠(2eq,9.99g,105.99g/mol,94.34mmol)加入到乙二醇二胺醚(200g,化合物7的20倍质量)和水(200g,化合物7的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.43g,304.37g/mol,1.42mmol)和乙酸钯(II)(0.5%eq,0.053g,224.51g/mol,0.23mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物39粗品,化合物39粗品再经过柱层析后得到化合物39纯品(18.5g,收率82.6%),MS(EI):475(M+)。
将化合物39(18g,475g/mol,37.89mmol)加入到乙酸(360g,化合物39的20倍质量)和浓硫酸(360g,化合物39的20倍质量),混匀后再将N-溴代琥珀酰亚胺(1.0eq,6.74g,177.98g/mol,37.89mmol)避光反应2h,反应液倒入冰水混合物中,快速搅拌,将洗出的固体滤出,得到化合物40粗品,化合物40粗品再经过柱层析后得到化合物40纯品(15.46g,收率73.8%),MS(EI):553(M+)。
将化合物40(15g,553g/mol,27.12mmol)、化合物37(1.1eq,12.33g,413.16g/mol,29.83mmol)和碳酸钠(2eq,5.75g,105.99g/mol,54.24mmol)加入到乙二醇二胺醚(300g,化合物36的20倍质量)和水(300g,化合物36的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.25g,304.37g/mol,0.81mmol)和乙酸钯(II)(0.5%eq,0.03g,224.51g/mol,0.14mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到化合物G190粗品,化合物G190粗品再经过柱层析后得到化合物G190纯品(17.26g,收率75.6%),MS(EI):842(M+)。
实施例16:
步骤1-6与实施例14基本相同,其余步骤如下:
将化合物36(15g,553g/mol,27.12mmol)、化合物41(1.1eq,13.34g,447.06g/mol,29.83mmol)和碳酸钠(2eq,5.75g,105.99g/mol,54.24mmol)加入到乙二醇二胺醚(300g,化合物36的20倍质量)和水(300g,化合物36的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(3%eq,0.25g,304.37g/mol,0.81mmol)和乙酸钯(II)(0.5%eq,0.03g,224.51g/mol,0.14mmol),升温至回流反应20h后,将有机相分出,水洗后减压浓缩,得到化合物G191粗品,化合物G191粗品再经过柱层析后得到化合物G191纯品(17.4g,收率76.2%),MS(EI):842(M+)。
以下将通过实施例和对照例对本发明进行详细的说明。下属实施例于对照例只是为了举例说明本发明,本发明的范围并不限于下述实施例和对照例。
《有机电致发光器件的制造》
应用例1:
其采用ITO作为反射层阳极基板材料,并以N2等离子或UV-Ozone对其进行表面处理.在阳极基板上方,向空穴注入层(HIL)沉积HAT-CN 10纳米厚度的HAT-CN,在其上方选使用NPD以120纳米厚度形成空穴传输层(HTL).在上述空穴传输层(HTL)上,选择本发明中的有机电致发光化合物G1真空蒸镀形成Green EML作为发光层,选择GD-1为dopant材料,掺杂约5%的25纳米厚度形成发光层,并在上方以1:1的比例混合蒸镀35纳米厚度的ETM和LiQ到电子输送层(ETL),之后在电子注入层(EIL)上以2纳米厚度的LiQ进行蒸镀.此后在阴极将镁(Mg)和银(Ag)以9:1的比例混合且以厚度为15纳米进行蒸镀,在上述阴极封口层上沉积65纳米厚度的N4,N4′-BIS[4-BIS(3-methylphenyl)Amino phenyl)]-N4,N4′-Diphenyl-[1,1′-Biphenyl]-4,4′Diamin(DNTPD)。
此外,在阴极表面以UV硬化胶合剂和含有除湿剂的封装薄膜(seal cap)进行密封,以保护有机电致发光器件不被大气中的氧气或水分所影响至此制备获得有机电致发光器件。
应用例2-16
分别以本发明有机电致发光化合物G2、G15、G40、G57、G69、G71、G105、G110、G120、G146、G182、G189、G190、G191、G192替换G1,其他部分与应用例1一致,据此制作出应用例2~16的有机电致发光器件。
对照例1、2
与应用例1的区别在于,使用GH-1及GH-2代替本发明的化合物作为绿光主体材料(Greenhost),其余与应用例1相同。上述应用例制造的有机电致发光器件及对照例制造的有机电致发光器件的特性是在电流密度为10mA/cm2的条件下测定的,结果如表1所示。
表1:
由如上表1的实验对比数据可知,采用本发明所述的化合物制备的有机电致发光器件与对照例相比,电压降低30%左右,发光效率提高一倍左右,寿命提高70%左右,由此可见,本发明的化合物能使器件的驱动电压大幅降低,有效减少了电能的消耗、显著提高了发光效率及发光器件的寿命。
Claims (7)
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为下列结构式化合物中的任意一种:
2.一种如权利要求1所述的有机电致发光化合物的制备方法,其特征在于,其制备方法如下:
将结构通式为的化合物Ⅰ、/>的化合物Ⅱ和碳酸钠加入到乙二醇二胺醚和水的混合溶液中,搅拌混匀后再依次加入三(邻甲苯基)膦和乙酸钯(II),升温至回流反应15-20h后,将有机相分出,水洗后减压浓缩,再经过柱层析后得到所述有机电致发光化合物。
3.如权利要求1所述的有机电致发光化合物在制备有机电致发光器件中的应用。
4.一种包含如权利要求1所述的有机电致发光化合物的有机电致发光器件,其特征在于,所述有机电致发光器件为阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层以及阴极顺次堆积的构造;
其中,阳极和发光层之间还设置有电子阻隔层;
阴极和发光层之间还设置有空穴阻隔层;
阴极表面还设置有覆盖层。
5.如权利要求4所述的有机电致发光器件,其特征在于,所述空穴传输层、电子阻隔层、空穴阻隔层、电子传输层、发光层或者覆盖层中的至少一层包含至少一种如权利要求1所述的有机电致发光化合物。
6.如权利要求4或5所述的有机电致发光器件,其特征在于,空穴传输层和/或电子阻隔层中包括至少一种如权利要求1所述的有机电致发光化合物。
7.一种包含权利要求6所述的有机电致发光器件的有机电致发光显示设备。
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