CN113336796B - 一种含磷杂吲哚并噁唑类材料及应用 - Google Patents
一种含磷杂吲哚并噁唑类材料及应用 Download PDFInfo
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- CN113336796B CN113336796B CN202110570987.0A CN202110570987A CN113336796B CN 113336796 B CN113336796 B CN 113336796B CN 202110570987 A CN202110570987 A CN 202110570987A CN 113336796 B CN113336796 B CN 113336796B
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- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
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Abstract
Description
技术领域
本发明涉及一种含磷杂吲哚并噁唑类材料及应用,属于有机光电材料技术领域。
背景技术
有机电致发光二极管(OLED:Organic light Emission Diodes)器件技术目前已经应用于照明及显示装置,具有低能耗、色彩丰富、响应速度快等优点,有望替代现有的液晶显示和荧光灯照明,应用前景十分广泛。
近些年,随着OLED技术在照明和显示两大领域的不断推进,提升有机电致发光技术的竞争力,特别是提高有机地电致发光器件效率、寿命和降低驱动电压等性能的材料开发和器件结构研究具有更加重要的意义。性能优异的新材料可以提高效率和寿命同时进一步降低屏体的成本,寻找更优性能的材料,也是有机电致发光领域技术发展的关键因素。一个效率好寿命长的有机电致发光器件通常是器件结构与各种有机材料的优化搭配的结果。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,必须选择更适合,具有高性能的OLED功能材料,才能实现器件的高效率、长寿命和低电压的综合特性。当前OLED显示照明产业的实际需求而言,目前OLED材料的发展还远远不够,落后于面板制造企业的要求,作为材料企业开发更高性能的有机功能材料的开发显得尤为重要。
发明内容
本发明针对现有技术存在的不足,提供一种含磷杂吲哚并噁唑类材料及应用,所述含磷杂吲哚并噁唑类材料应用于OLED元件,OLED元件可进行低电压驱动、长寿命并且效率高,满足面板商的要求。
本发明解决上述技术问题的技术方案如下:一种含磷杂吲哚并噁唑类材料,所述含磷杂吲哚并噁唑类材料以含磷杂吲哚并噁唑为主体,其分子结构的通式如通式(1)所示:
通式(1)中,其中R表示为取代或未取代的C6-60芳基、含有一个或多个杂原子的取代或未取代的5-60元杂芳基;所述杂原子为氮、氧或硫。
进一步的,通式(1)中,R为苯、联苯、三联苯、萘、蒽、菲、芘、联萘、联蒽、荧蒽、苯并蒽、芴、苯并芴、N-苯基咔唑、N-萘基咔唑、N-苯基苯并咔唑、二苯并呋喃、二苯并噻吩中的一种。
进一步的,所述的R选自如下结构式中的任意一个:
进一步的,所述含磷杂吲哚并噁唑类材料为如下结构式(1)~(54)中的任意一个:
本发明还公开了所述含磷杂吲哚并噁唑类材料的应用:
所述的含磷杂吲哚并噁唑类材料应用于有机电致发光二极管。
优选的,所述的含磷杂吲哚并噁唑类材料作为发光层主体材料应用在有机电致发光二极管。
本发明的有益效果是:
磷杂吲哚并噁唑类材料具有特殊的生物活性和光电性能,可以成为良好的发光层材料。选用本发明的化合物作为OLED器件发光材料,对比现有材料应用的OLED发光器件,器件的发光效率以及寿命等性能均有良好的表现,电压驱动低,寿命长,效率高;磷杂吲哚并噁唑类材料在OLED器件的应用上具有很大的应用价值和商业价值,具备良好的产业化前景。
附图说明
图1为实施例所述电致发光器件的结构示意图;
图中,1ITO基板,2ITO阳极层,3空穴注入层,4空穴传输层,5发光层,6电子传输层,7电子注入层,8阴极反射电极层。
具体实施方式
为使本发明的上述目的、特征和优点能够更加明显易懂,下面对本发明的具体实施方式做详细的说明。在下面的描述中阐述了很多具体细节以便于充分理解本发明。但是本发明能够以很多不同于在此描述的其它方式来实施,本领域技术人员可以在不违背本发明内涵的情况下做类似改进,因此本发明不受下面公开的具体实施例的限制。
除非另有定义,本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施方式的目的,不是旨在于限制本发明。
实例中有共用的中间体化合物I,8-氯-2,5-二苯基-5H-苯并[2,3]磷杂吲哚[6,5-d]噁唑-5-氧,其合成方法如下:
中间体C的制备:在通氮气的2L三口瓶加入50.0g化合物A(188.68mmol),51.0g化合物B(471.69mmol),加入500g DMF(N,N-二甲基甲酰胺),在通氮气保护下,加入5.23gDPPF(1,1'-双(二苯基膦)二茂铁)(9.434mmol),料加毕,升温至130.0~140.0℃保温3~4h。TLC检测原料反应完毕,降至室温后水洗至中性,140℃脱干溶剂。用甲苯:石油醚=1:4重结晶。得35.0g化合物C,收率57.76%,纯度98.0%。
中间体F的制备:在通氮气的2L三口瓶加入125.8g(4.0mol)乙醇,降温0.0~10.0℃滴入化合物D 200g(0.684mol),滴加毕,保温2~3h后,控温20℃以下滴加三乙胺103.6g(1.026mol),滴毕保温5小时TLC检测原料反应完毕,先甲苯萃取后加水水洗至中性,分水过柱,95℃脱干溶剂,得180.0g化合物F,收率92.8%,纯度95.0%。
中间体G的制备:在通氮气的2L三口瓶加入180.0g化合物F(0.352mol),900.0g四氢呋喃溶液,料加毕,搅拌升温至50.0~60.0℃,滴加溴苯格式试剂(0.369mol),滴加毕保温2~3h。TLC检测原料反应完毕,甲苯萃取后过柱,95.0℃脱干溶剂。用甲苯:正己烷=1:3重结晶。得150.0g化合物G,收率74.8%,纯度99.0%。
中间体H的制备:在通氮气的1L三口瓶加入45.2g碳酸钾(327.07mmol),105.5g水,35.0g化合物C(109.02mmol),34.4g化合物G(109.02mmol),加入500g甲苯,在通氮气保护下,加入醋酸钯0.244g(1.09mmol)和X-Phos(2-二环己基磷-2′,4′,6′-三异丙基联苯)1.03g(2.18mmol),料加毕,升温至75.0~85.0℃保温10~12h。TLC检测原料反应完毕,降至室温后水洗至中性,过柱后95℃脱干溶剂。用甲苯:石油醚=1:2重结晶。得43.2.g化合物H,收率77.9%,纯度99.5%。
中间体I的制备:在通氮气的1L三口瓶加入83.0g碳酸铯(254.75mmol),43.2g化合物H(84.92mmol),加入500g NMP(N-甲基吡咯烷酮),在通氮气保护下,加入醋酸钯0.19g(0.84mmol)和三环己基膦0.47g(1.68mmol),料加毕,升温至130.0~140.0℃保温8~10h。TLC检测原料反应完毕,降至室温加入500g甲苯后水洗至中性,过柱后140℃脱干溶剂。用甲苯:石油醚=1:2重结晶。得15.2g化合物I,收率41.8%,纯度99.9%。
HPLC-MS:化合物I理论分子量为427.82,实际检测结果分子量为428.14。
1HNMR:δ7.23-7.37(5H,m),7.44(1H,t),7.57-7.76(3H,m),7.81(1H,dd,J=8.4,0.4Hz),7.96(2H,m),8.08(1H,d,J=0.5Hz),8.39(1H.d,j=0.5Hz)8.53(1H,dd,J=1.8,0.4Hz)。
13CNMR(101MHz,CDCl3)δ(ppm):149.8,141.9,111.0,128.7,131.9,132.5,142.2,130.7,142.1,128.9,124.3,128.6,128.2,128.3,132.7,127.9,127.9,128.8,128.9,131.2,130.8,130.9,127.1,130.6,164.4。
实施例1:化合物1的合成
化合物1的合成路线
化合物1的制备
在通氮气的500mL三口瓶加入10.0g化合物I(23.37mmol),9.69g碳酸钾(70.12mmol),22.61g水,加入100g甲苯,在通氮气保护下,加入0.27g Pd(PPh3)4(四三苯基膦合钯)(0.2337mmol),料加毕,升温至60.0~65.0℃滴加化合物1a 4.02g的四氢呋喃溶液,滴毕保温4~5h。TLC检测原料反应完毕,降至室温后用热水洗至中性后过硅胶柱,然后95℃脱干溶剂。用甲苯:乙醇=2:3重结晶。得8.3g化合物1,收率75.6%,纯度99.91%。
HPLC-MS:材料理论分子量为469.47,实际检测结果分子量为469.1。
1H NMR:δ(ppm):7.26-7.37(4H,m),7.41-7.57(4H,m),7.64-7.82(4H,m),7.90(2H,dd,J=7.9,1.8,Hz),8.02(2H,m),8.39(1H,dd,J=2.0,0.5Hz)。
13CNMR(101MHz,CDCl3):δ(ppm):127.9,127.8,128.9,128.9,127.0,126.0,124.3,131.1,131.6,142.1,130.8,130.8,132.7,138.5,127.9,128.9,130.9,127.8,130.5,128.3,128.3,141.1,149.8,141.9,127.1,164.3,111.0,128.8,127.8,127.6,138.2。
实施例2化合物3的合成
化合物3的合成路线
化合物3的制备
在通氮气的500mL三口瓶加入10.0g化合物I(23.37mmol),9.69g碳酸钾(70.12mmol),22.61g水,加入100g甲苯,在通氮气保护下,加入0.27g Pd(PPh3)4(四三苯基膦合钯)(0.2337mmol),料加毕,升温至70.0~75.0℃滴加4.02g化合物3a(23.37mmol)的四氢呋喃溶液,滴毕保温4~5h。TLC检测原料反应完毕,降至室温后用热水洗至中性后过硅胶柱,然后95℃脱干溶剂。用甲苯:乙醇=1:2.5重结晶。得10.1g化合物3,收率82.1%,纯度99.85%。
HPLC-MS:材料理论分子量为519.53,实际检测结果分子量为520.0。
1H NMR:δ(ppm):7.25-7.37(4H,),7.44(1H,t),7.48-7.83(6H,m),8.03-8.15(4H,m),8.16(1H,d,J=0.5Hz),8.21-8.34(4H,m),8.24(1H,ddt,J=7.4,2.0,1.9,0.4Hz),8.52(1H,dd,J=1.9,0.5Hz)。
13CNMR(101MHz,CDCl3)(ppm):131.1,142.1,128.0,128.8,141.8,128.9,128.9,127.7,130.8,130.8,149.8,128.3,128.3,128.6,139.1,135.6,124.3,163.3,126.0,128.3,141.1133.7,126.5,131.9,130.8,139.2,127.8,132.6,127.1,1278,127.9,125.7,131.3,111.0,129.0。
实施例3:化合物6的合成
化合物6的合成路线
化合物6的制备
在通氮气的500mL三口瓶加入10.0g化合物I(23.37mmol),9.69g碳酸钾(70.12mmol),22.61g水,加入100g二氧六环,在通氮气保护下,加入0.05g醋酸钯(0.2337mmol)和0.19g S-Phos(2-二环己基膦基-2′,6′-二甲氧基联苯基)(0.4674mmol),料加毕,升温至70.0~75.0℃滴加5.19g化合物6a(23.37mmol)的四氢呋喃溶液,滴毕保温5~6h。TLC检测原料反应完毕,降至室温后用热水洗至中性后过硅胶柱,然后95℃脱干溶剂。用甲苯:乙醇=2:2重结晶。得9.7g化合物6,收率72.87%,纯度99.9%。
HPLC-MS:材料理论分子量为569.59,实际检测结果分子量为570.1。
1H NMR:δ(ppm):7.24-7.37(4H,m),7.44(1H,t,J=7.6,1.7Hz),7.67-7.90(7H,m),8.12(1H,dd,J=5.8,2.0Hz),8.15-8.22(4H,m),8.69(1H,dd,J=5.8,0.5Hz),8.95(1H,t,J=0.5Hz)。
13CNMR(101MHz,CDCl3):δ(ppm):111.0,164.3,142.1,130.8,130.8,130.6,131.9,139.1,132.6,122.6,,131.1,126.7,131.3,141.9,126.9,132.7,130.0,127.1,149.8,129.0,127.8,127.6,128.3,128.3,124.3,126.5,127.6130.7,128.9,140.0,127.9,127.9,142.1,122.4,128.0,128.9,128.9,128.0,130.8。
实施例4:化合物9的合成
化合物9的合成路线
化合物9的制备
在通氮气的500mL三口瓶加入10.0g化合物I(23.37mmol),7.43g碳酸钠(70.12mmol),17.33g水,加入100g二甲苯,在通氮气保护下,加入0.05g醋酸钯(0.2337mmol)和0.19g S-Phos(2-二环己基膦基-2′,6′-二甲氧基联苯基)(0.4674mmol),料加毕,升温至60.0~65.0℃滴加4.63g化合物9a(23.37mmol)的四氢呋喃溶液,滴毕保温3~4h。TLC检测原料反应完毕,降至室温后用热水洗至中性后过硅胶柱,然后95℃脱干溶剂。用甲苯:乙醇=1:2重结晶。得10.1g化合物9,收率79.21%,纯度99.83%。
HPLC-MS:材料理论分子量为545.57,实际检测结果分子量为546.0。
1H NMR:δ7.26-7.37(4H,m),7.68-7.84(5H,7.80(dd,J=7.9,1.8,1.5,0.4Hz),7.73(tdd,J=7.7,1.9,1.5Hz),7.75m),8.01(2H,ddd,J=7.3,1.8,0.5Hz),8.07-8.19(6H,m),8.17(1H,d,J=0.5Hz),8.25(1H,dd,J=7.0,0.5Hz),8.39(1H,dd,J=1.8,0.5Hz)。
13CNMR(101MHz,CDCl3):δ(ppm):131.9138.2132.6164.3127.5127.5128.8128.8128.9130.8127.9127.9140.3142.6130.8130.8128.3128.3127.0127.0142.1142.1149.8141.9131.1127.8127.6127.51127.51111.0128.9127.1139.0132.7128.9128.9124.3。
实施例5:化合物33的合成
化合物33的合成路线
化合物33的制备
在通氮气的500mL三口瓶加入10.0g化合物I(23.37mmol),9.69g碳酸钾(70.12mmol),22.61g水,加入100g二氧六环,在通氮气保护下,加入0.203g Pd2(dba)3(三(二亚苄基丙酮)二钯)(0.2337mmol)和X-Phos 0.22g(2-二环己基磷-2′,4′,6′-三异丙基联苯)(0.4674mmol),料加毕,升温至80.0~85.0℃滴加4.96g化合物33a(23.37mmol)的四氢呋喃溶液,滴毕保温7~8h。TLC检测原料反应完毕,降至室温后用热水洗至中性后过硅胶柱,然后95℃脱干溶剂。用甲苯:石油醚=1:2重结晶。得9.8g化合物33,收率74.9%,纯度99.86%。
HPLC-MS:材料理论分子量为559.55,实际检测结果分子量为560.6。
1H NMR:δ7.26-7.37(4H,m),7.44(1H,tt,J=7.6,1.7Hz),7.60-7.77(5H,m),7.82-7.94(2H,m),7.99(1H,dd,J=5.9,2.0Hz),8.04(1H,t,J=0.5Hz),8.06-8.12(3H,m),8.16(1H,d,J=0.5Hz),8.24(1H,dd,J=5.9,0.5Hz),8.34(1H,t,J=0.5Hz),8.49-8.55(2H,m)。
13CNMR(101MHz,CDCl3)δ(ppm):130.8,130.7,142.1,128.9,126.2,127.3,117.9,121.4,130.8,130.2,155.6,142.1,127.9,126.9,127.8,126.9,128.9,131.9128.3,128.3,141.8,111.6,124.6,1237,149.8,132.6,124.3,131.1,127.2,111.0,155.2,121.1,127.1,164.3,132.7,127.6,126.4。
实施例6:化合物34的合成
化合物34的合成路线
化合物34的制备
在通氮气的500mL三口瓶加入10.0g化合物I(23.37mmol),9.69g碳酸钾(70.12mmol),22.61g水,加入100g二氧六环,在通氮气保护下,加入0.203g Pd2(dba)3(三(二亚苄基丙酮)二钯)(0.2337mmol)和0.22g X-Phos(2-二环己基磷-2′,4′,6′-三异丙基联苯)(0.4674mmol),料加毕,升温至80.0~85.0℃滴加5.33g化合物34a(23.37mmol)的四氢呋喃溶液,滴毕保温7~8h。TLC检测原料反应完毕,降至室温后用热水洗至中性后过硅胶柱,然后95℃脱干溶剂。用甲苯:石油醚=2:3重结晶。得9.6g化合物34,收率71.37%,纯度99.88%。
HPLC-MS:材料理论分子量为575.61,实际检测结果分子量为576.7。
1H NMR:δ7.26-7.37(4H,m),7.44(1H,t,J=7.6,1.7Hz),7.59-7.76(6H,m),7.82(1H,dd,J=7.0,2.0Hz),8.06-8.13(3H,m),8.16(1H,d,J=0.5Hz),8.22-8.28(2H,dd),8.42-8.53(4H,m)。
13CNMR(101MHz,CDCl3):δ(ppm):128.2,120.4,139.1,136.2,122.9,132.6,149.8,131.0,141.9,164.3,126.9,142.1,127.9,127.8,132.5,135.4,124.3,128.2,128.3,121.8,126.8,132.9,111.0128.9,142.1,128.6,128.9,138.4,131.9,138.6,130.8,130.2,127.6,127.8。
下面通过应用实施例1~6详细说明本发明合成的化合物在OLED器件上的应用效果。对比例:一种电致发光器件,其制备步骤包括:
将透明阳极电极ITO基板1在异丙醇中超声清洗10分钟,并暴露在紫外光下30分钟,随后用plasma处理10分钟;在ITO阳极层2上,通过真空蒸镀方式蒸镀空穴注入层材料HAT-CN,厚度为15nm,这层作为空穴注入层3;在空穴注入层3上,通过真空蒸镀方式蒸镀空穴传输层4材料NPB,厚度为40nm,该层为空穴传输层4;在空穴传输层4之上蒸镀发光层5,使用化合物a(如下图)作为主体材料,Ir(ppy)3作为掺杂材料,Ir(ppy)3和化合物a的质量比为5:9,厚度为30nm;在发光层之上,通过真空蒸镀方式蒸镀电子传输材料TPBI,厚度为50nm;在电子传输层6之上,真空蒸镀电子注入层7LiF,厚度为1.2nm,该层为电子注入层;在电子注入层7之上,真空蒸镀阴极Al(100nm),该层为阴极反射电极层8,制成所述电致发光器件。如图1所示。
应用例1
所述器件的制作工艺与对比例的完全相同,并且使用相同的基板材料和电极材料,并且电极材料的膜厚度相同,不同处仅将发光层主体材料分别换成了实施例1制备的化合物。
应用例2
所述器件的制作工艺与对比例的完全相同,并且使用相同的基板材料和电极材料,并且电极材料的膜厚度相同,不同处仅将发光层主体材料分别换成了实施例2制备的化合物。
应用例3
所述器件的制作工艺与对比例的完全相同,并且使用相同的基板材料和电极材料,并且电极材料的膜厚度相同,不同处仅将发光层主体材料分别换成了实施例3制备的化合物。
应用例4
所述器件的制作工艺与对比例的完全相同,并且使用相同的基板材料和电极材料,并且电极材料的膜厚度相同,不同处仅将发光层主体材料分别换成了实施例4制备的化合物。
应用例5
所述器件的制作工艺与对比例的完全相同,并且使用相同的基板材料和电极材料,并且电极材料的膜厚度相同,不同处仅将发光层主体材料分别换成了实施例5制备的化合物。
应用例6
所述器件的制作工艺与对比例的完全相同,并且使用相同的基板材料和电极材料,并且电极材料的膜厚度相同,不同处仅将发光层主体材料分别换成了实施例6制备的化合物。
对比例1和应用例1~6所制作的OLED发光器件的测试结果如表1所示。
表1 OLED发光器件的测试结果
由表1分析得出,选用本发明的化合物作为OLED器件发光材料,对比现有材料应用的OLED发光器件,器件的发光效率以及寿命等性能均有良好的表现;在OLED器件的应用上具有很大的应用价值和商业价值,具备良好的产业化前景。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (6)
2.根据权利要求1所述的一种含磷杂吲哚并噁唑类材料,其特征在于,通式(1)中,R为苯、联苯、三联苯、萘、蒽、菲、芘、联萘、联蒽、苯并蒽、二苯并呋喃、二苯并噻吩中的一种。
5.一种根据权利要求1-4任意一项所述的一种含磷杂吲哚并噁唑类材料的应用,其特征在于,所述的含磷杂吲哚并噁唑类材料应用于有机电致发光二极管。
6.根据权利要求5所述的一种含磷杂吲哚并噁唑类材料的应用,其特征在于,所述的含磷杂吲哚并噁唑类材料作为发光层主体材料应用在有机电致发光二极管。
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