CN114874169A - 有机化合物、包含该有机化合物的材料和有机发光器件 - Google Patents
有机化合物、包含该有机化合物的材料和有机发光器件 Download PDFInfo
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- CN114874169A CN114874169A CN202210268082.2A CN202210268082A CN114874169A CN 114874169 A CN114874169 A CN 114874169A CN 202210268082 A CN202210268082 A CN 202210268082A CN 114874169 A CN114874169 A CN 114874169A
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Classifications
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- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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Abstract
Description
技术领域
本发明属于有机光电材料领域,具体涉及有机发光元件用有机化合物、含有这种有机化合物的发光器件材料及发光器件,更具体而言,涉及一种具有优异的色纯度、高亮度及高发光效率的可溶性有机化合物以及使用该化合物的OLED器件。
背景技术
有机电激发光二极管(Organic Light-Emitting Diode,简称为OLED),该发光器件具有薄型且能在低驱动电压下高亮度发光以及能通过选择发光材料而进行多色发光的特征,因此倍受关注。该研究自从由柯达公司的C.W.Tang等揭示有机薄膜元件能以高亮度发光以来,大量OLED行业研究人员对于其应用,做了很多研究和推进。有机薄膜发光器件被广泛应用在各种主显示屏等中,其实用化取得长足的进展。尽管有机电致发光的研究进展非常迅速,但仍有很多亟待解决的问题,其中发光的高效利用及减少发光损耗是一个很大的课题。
根据OLED的出光方式,可以分为底发射有机发光器件和顶发射有机发光器件。最初的OLED都是底发射型器件,器件的结构从上至下依次是:不透明的金属阴极/有机功能层/透明阳极,光线从阳极出射,因而称为底发射。顶发射OLED是指光从器件顶部射出的OLED。其中,顶发射OLED由于不受基板是否透光的影响,可有效提高显示面板的开口率,拓展了基板上TFT电路的设计,丰富了电极材料的选择,有利于器件与TFT电路的集成。如果器件是以底发射形式出光,光经过基板的时候就会被基板上的TF和金属配线阻挡,这样就会影响实际的发光面积。如果光线是从器件上方出射,采用顶发射器件结构,那么基板的线路设计就不会影响器件的出光面积,相同亮度下OLED的工作电压更低,可以获得更长的使用寿命。因此,顶发射器件是小像素、高PPI的小屏如手机等主动显示的首选。
现有技术中,为了提高顶发射有机发光元件的出光效率,采用的方法有在使发光层的光透过的上部半透明金属电极上形成有机覆盖层,以此调节光学干涉距离,抑制外光反射和由表面等离子体能量移动引起的消光等(参见专利文献1-5,专利文献1:WO2001/039554;专利文献2:CN105849113B;专利文献3:JP2007-103303;专利文献4:CN 109535125;专利文献5:CN103579521)例如,专利文献2记载,所用的有机覆盖层的材料是具有特定化学结构的芳香胺化合物等,专利文献4记载所用的有机覆盖层的材料是二苯并六元环的为核心的化合物,专利文献5记载,使用的有机覆盖层材料是含有芴的芳香胺化合物等。
发明内容
如上所述,现有技术中使用具有高折射率的特定结构的芳香胺衍生物或使用符合特定参数要求的材料作为有机覆盖层材料来改善光取出效率和色纯度,但是尚未解决兼顾发光效率和色纯度的问题,特别是在制备蓝光发光元件的情况。
本发明提供一种用于提高有机发光元件的光取出效率以及改善色纯度的有机化合物、含有该化合物的有机发光元件材料和有机器件。本发明提供的含有该有机化合物的有机电致发光器件具有热稳定性好,发光效率高、使用寿命长的优点。
本发明提供一种有机化合物,该化合物其具有下式(1)所示的结构:
式(1)中,X1和X2相同或不相同,独立选自单键、O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-;
X3和X4相同或不相同,独立选自O、S、-SO2-、-SO-、-CR8R9-、-NR10-、-SiR11R12-、-SeR13R14-;
Ar1和Ar2相同或不相同,独立选自如下任一个取代基团:
其中,Ar3、Ar4和Ar5独立选自取代或未取代的C6-C60芳基,且Ar3不为苯基;
X5选自O、S、-NR15-、-CR16R17-;
R1-R17相同或不相同,独立选自氢、氘、氰基、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C1-C60杂烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环;
*表示取代基的连接位置。
本发明的有机化合物可以用作有机发光器件的覆盖层材料可实现高发光效率及色纯度。本发明的有机发光器件可以为有机光伏器件、有机电致发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管,还可以用于显示或照明装置,如有机EL显示器或照明的光源、标示板和标识灯等场合,使用寿命长。
具体实施方式
本发明提供的一种有机化合物,其具有下式(1)所示的结构:
式(1)中,X1和X2相同或不相同,独立选自单键、O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-;
X3和X4相同或不相同,独立选自O、S、-SO2-、-SO-、-CR8R9-、-NR10-、-SiR11R12-、-SeR13R14-;
Ar1和Ar2相同或不相同,独立选自如下任一个取代基团:
其中,Ar3、Ar4和Ar5独立选自取代或未取代的C6-C60芳基,且Ar3不为苯基;
X5选自O、S、-NR15-、-CR16R17-;
R1-R17相同或不相同,独立选自氢、氘、氰基、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C1-C60杂烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环;
*表示取代基的连接位置。
一些实施方式中,式(1)中,X3和X4相同,且Ar1和Ar2相同。
一些实施方式中,式(1)中,Ar3为萘基。
一些实施方式中,式(1)中,X1和X2相同,选自O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-,其中R1-R7独立选自氢、氘、氰基、甲基、苯基、萘基、吡啶基或者与临近的原子键合成环。
一些实施方式中,式(1)中,X1和X2不同,X1选自单键、O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-,X2选自O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-,其中R1-R7独立选自氢、氘、氰基、甲基、苯基、萘基、吡啶基或者与临近的原子键合成环。
一些实施方式中,式(1)中,上述有机化合物选自以下任一个化学结构:
上述式(1)所示的有机化合物的合成可以使用已知的方法进行。例如,使用镍、钯等过渡金属的交叉偶合反应。其他合成方法是使用镁或锌等过渡金属的C-C、C-N偶联生成反应。上述反应,限于反应条件温和、各种官能团的选择性优越等特点,优选Suzuki、Buchwald反应。本发明的通式(1)所示的有机化合物可以单独使用也可以跟其他材料混合使用在有机发光元件中。
本发明的有机电致发光器件是包含通式(1)所示有机化合物的发光元件,该发光元件包含基板、第一电极、有机物层、第二电极以及覆盖层,优选的器件结构可包括基板、位于基板上的第一电极、位于第一电极上的有机物层、位于有机物层上的第二电极以及位于第二电极外侧的覆盖层,本发明的第二电极外侧是指背离第一电极的一侧。本发明的有机物层可以包含发光层、空穴注入层、空穴传输层、电子传输层、电子注入层作为有机物层的结构。发光元件的有机物层可以由单层结构形成,也可以由层叠包含发光层、空穴注入层、空穴传输层、电子传输层、电子注入层在内的多层结构形成;同时有机物层还可以包含一层或多层结构,例如,空穴传输层可以包含第一空穴传输层以及第二空穴传输层。本发明的发光元件中,除了所述覆盖层包含有本发明的有机化合物外,其它层均可以使用现有公知技术的用于所述层的任何材料。本发明的发光元件中,基板材料可选用典型的有机发光元件中使用的任何基板,可以是钠玻璃或无碱玻璃或者透明柔性基板,也可以是不透明材料如硅或不锈钢的基板,还可以是柔性聚酰亚胺薄膜。不同基板材料具有不同的性能,应用方向不同。
作为本发明的空穴传输层,可通过将空穴传输材料的一种或二种以上层叠或混合的方法,或通过使用空穴传输材料和高分子粘合剂的混合物的方法来形成。空穴传输材料需要在施加了电场的电极之间高效率地传输来自正极的空穴,因此希望空穴注入效率高、能够高效率地传输注入的空穴。因此,要求空穴传输材料具有适当电离势,适当的能级并且具有大的空穴迁移率,进一步材料稳定性优异,制造及使用过程中不容易产生会成为陷阱的杂质。对满足这样的条件的物质,没有特别限定,例如可以是咔唑衍生物、三芳胺衍生物、联苯二胺衍生物、芴衍生物、酞菁类化合物、六腈六氮杂苯并菲类化合物、喹吖啶酮类化合物、苝衍生物、蒽醌类化合物、F4-TCNQ、聚苯胺、聚噻吩、聚乙烯咔唑等,但不限于此。
作为本发明的发光层材料,可以包含主体材料(也称基质材料)和掺杂材料(也称客体材料),发光层材料可包含多个主体材料和多个掺杂材料。发光层可为单一的发光层,也可为横向或纵向叠加在一起的复合发光层。对于掺杂材料的种类选择,可以为荧光材料,也可以为磷光材料。对于掺杂材料的用量选择,优选0.1-70%质量,更优选为0.1-30质量%、进一步优选为1-30质量%、更进一步优选为1-20质量%、特别优选为1-10质量%。可用于本发明的荧光掺杂材料可包括:稠合多环芳族衍生物、苯乙烯基胺衍生物、稠环胺衍生物、含硼化合物、吡咯衍生物、吲哚衍生物、咔唑衍生物等,但不限于此。可用于本发明的磷光掺杂材料可包括:重金属配合物、磷光发光性的稀土类金属配合物等,但不限于此。重金属配合物可举出例如铱配合物、铂配合物、锇配合物等;稀土类金属配合物可举出例如铽络合物、铕络合物等,但不限于此。可用于本发明的主体材料可包括:主体材料包括稠合芳族环衍生物、含杂环的化合物等。具体地,稠合芳族环衍生物包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲衍生物、荧蒽衍生物等,以及含杂环的化合物包括咔唑衍生物、二苯并呋喃衍生物、二苯并噻吩衍生物、嘧啶衍生物等,但不限于此。
作为本发明的电子传输材料,优选具备良好电子迁移率的物质,同时具备合适的HOMO和LUMO能级。可作为本发明的电子传输材料包括:金属配合物、氧杂噻唑衍生物、噁唑衍生物、二氮唑衍生物、氮杂苯衍生物、菲罗啉衍生物、二氮蒽衍生物、含硅杂环类化合物、含硼杂环类化合物、氰基类化合物、喹啉衍生物、苯并咪唑衍生物等,但不限于此。
作为本发明的电子注入材料,优选具有传输电子能力的物质,同时具有从阴极注入电子的效应,具有优异的薄膜形成能力。可作为本发明的电子注入材料包括:碱金属化合物,例如氧化锂、氟化锂、8-羟基喹啉锂、氧化锂硼、碳酸铯、8-羟基喹啉铯、硅酸钾、氟化钙、氧化钙、氟化镁、氧化镁;芴酮;含氮五元环衍生物,例如,噁唑衍生物、恶二唑衍生物、咪唑衍生物;金属配合物;蒽醌二甲烷、联苯醌、蒽酮衍生物等,但不限于此,这些化合物可以单独使用,也可与其他材料混合使用。
作为本发明的阴极材料,优选具有低功函数的材料,以便容易地将电子注入有机层。可用于本发明的阴极材料包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、铝、银、锡、铅,或者它们的合金;以及多层材料,例如LiF/Al或LiO2/Al,但不限于此。本发明所述的有机物层材料,它们在使用时,可单独成膜形成单层结构,也可和其他材料一起混合成膜形成单层结构,或者形成单独成膜的单层的层叠结构、混合成膜的单层的叠层结构、单独成膜的单层和混合成膜的单层的叠层结构,但不限于此。
本发明的有机电致发光器件可以通过依次层叠上述的结构而制造。制造方法可使用干式成膜法、湿式成膜法等公知方法。作为干式成膜法的具体例,可举出真空蒸镀法、溅射法、等离子体法、离子电镀法等。作为湿式成膜法的具体例,可举出旋涂法、浸渍法、流延法、喷墨法等各种涂布法,但不限于此。本发明所述有机发光器件可广泛应用于面板显示、照明光源、柔性OLED、电子纸、有机太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。上述有机电致发光器件的制造在以下实施例中具体地进行说明。但是,下述实施例只是用于例示说明书,说明书的范围并不限定于此。
本发明的有机化合物用以下实施例举例说明,但并不限于这些实施例举例的有机化合物和合成方法。本发明的溶剂购于国药,一些常用的OLED原料及中间体类等产品购于国内的OLED中间体厂商;各种钯催化剂、配体等购于贵研铂业股份有限公司。1H-NMR数据使用JEOL(400MHz)核磁共振仪来测定,HPLC数据使用岛津LC-20AD高效液相仪来测定。实施例中使用物质为:
实施例1
化合物1的合成
在氩气氛围下,向反应容器中加入化合物1-A 32.6克(100mmol),化合物1-B 30.7克(210mmol),Pd(PPh3)2Cl2 1.4克(2mmol),1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,大量固体析出,过滤,滤饼用水搅洗3次,真空干燥。粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到31.4克化合物1-C,收率85%,HPLC纯度99.5%。
在氩气氛围下,向反应容器中加入化合物1-C 36.9克(100mmol),化合物1-D 36.1克(210mmol),XPhos Pd G3 1.7克(2mmol),1.5M碳酸钠水液200ml(300mmol)和四氢呋喃1000ml(THF),加热回流搅拌一晚。冷却至室温,加入1500ml水,大量固体析出,过滤,滤饼用水搅洗3次,真空干燥。粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到31.4克化合物1,收率85%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.46(s,2H),8.11(d,2H),8.00(d,2H),7.96(d,2H),7.93(d,2H),7.88(d,2H),7.83(s,2H),7.79(s,2H),7.61~7.59(m,4H),7.07(s,4H).
实施例2
化合物5的合成
除了起始原料更换为5-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.03(m,2H),7.98(d,2H),7.88(d,2H),7.83(d,2H),7.82(d,2H),7.79(d,2H),7.76(s,2H),7.54(d,2H),7.39~7.31(m,4H),7.07(s,4H).
实施例3
化合物18的合成
除了起始原料更换为18-D以外,其他与实施例1相同。
1HNMR(DMSO):δ7.88(d,2H),7.83(d,2H),7.79(d,2H),7.74(m,4H),7.38(d,4H),7.07(s,4H).
实施例4
化合物37的合成
除了起始原料更换为37-A、37-C和37-D以外,其他与实施例1相同。
1HNMR(DMSO):δ9.27(s,2H),8.85(d,2H),8.52(d,2H),8.15(d,2H),7.99(d,2H),7.92(d,2H),7.90(d,2H),7.75(s,4H),7.68(m,2H),7.63(m,2H),7.07(s,4H).
实施例5
化合物44的合成
除了起始原料更换为776-A和776-B以外,其他与实施例1相同。
1HNMR(DMSO):δ8.95(d,2H),8.50(d,2H),8.20(d,2H),8.12(s,2H),8.09(d,2H),7.99(d,2H),7.96(d,2H),7.92(d,2H),7.77(m,2H),7.52(m,4H),7.39(m,2H),7.25(d,4H),7.07(s,4H).
实施例6
化合物63的合成
除了起始原料更换为63-D以外,其他与实施例1相同。
1HNMR(DMSO):δ9.51(s,2H),9.32(s,2H),8.52(d,2H),8.12(s,2H),7.99(d,2H),7.92(d,2H),7.84(s,2H),7.76(s,4H),7.63(d,2H),7.07(s,4H).
实施例7
化合物73的合成
除了起始原料更换为73-A、73-C和73-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.52(d,2H),8.31(d,2H),8.18(s,2H),8.15(d,2H),8.08(s,4H),8.07(d,2H),8.04(m,2H),7.92(d,2H),7.74(d,2H),7.70(d,2H),7.68(d,2H),7.07(s,4H).
实施例8
化合物85的合成
除了起始原料更换为73-A、85-B、85-C和85-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.18(s,2H),8.07(d,4H),7.74(d,2H),7.68(d,2H),7.60(m,6H),7,30(s,4H),7.07(s,4H).
实施例9
化合物90的合成
除了起始原料更换为73-A、73-C和90-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.18(s,2H),7.96(d,2H),7.75(d,2H),7.74(d,2H),7.68(d,2H),7.49(m,4H),7.41(s,2H),7.25(m,12H),7.07(s,4H),
实施例10
化合物112的合成
除了起始原料更换为112-A、112-C和112-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.18(s,2H),8.09(d,2H),7.90(d,2H),7.89(s,2H),7.78(d,2H),7.74(d,2H),7.68(d,2H),7.55(d,2H),7.38(m,2H),7.28(m,2H),7.26(m,4H),7.18(m,2H),7.10(m,2H),7.07(s,4H).
实施例11
化合物141的合成
除了起始原料更换为141-A和141-C以外,其他与实施例1相同。
1HNMR(DMSO):δ8.46(s,2H),8.18(s,2H),8.11(d,2H),8.00(d,1H),7.96(d,2H),7.93(d,2H),7.89(d,2H),7.74(d,2H),7.68(d,2H),7.61(m,2H),7.59(m,2H),7.45(d,2H),7.28(m,2H),7.27(m,2H),7.07(s,4H)
实施例12
化合物176的合成
除了起始原料更换为176-A和176-C以外,其他与实施例1相同。
1HNMR(DMSO):δ8.46(s,2H),8.30(d,2H),8.13(d,2H),8.11(d,2H),8.00(d,2H),7.96(d,2H),7.93(d,2H),7.89(s,2H),7.62(m,2H),7.61(m,2H),7.59(m,2H),7.50(d,2H),7.07(s,4H).
实施例13
化合物181的合成
除了起始原料更换为176-A、176-C和181-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.45(d,2H),8.30(d,2H),8.24(d,2H),8.20(s,2H),8.13(d,2H),7.94(d,2H),7.93(d,2H),7.89(s,2H),7.62(m,2H),7.58(m,1H),7.56(m,2H),7.50(d,2H),7.49(m,2H),7.07(s,4H).
实施例14
化合物194的合成
除了起始原料更换为176-A、176-C和194-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.30(d,2H),8.13(d,2H),8.09(d,2H),8.06(d,2H),7.99(d,2H),7.96(d,4H),7.89(s,2H),7.63(m,2H),7.62(m,2H),7.58(s,1H),7.55(s,2H),7.50(d,2H),7.38(d,2H),7.25(d,4H),7.07(s,4H).
实施例15
化合物228的合成
除了起始原料更换为228-A、228-C和228-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.04(s,2H),7.97(d,2H),7.84(d,2H),7.74(m,4H),7.38(d,4H),7.07(s,4H).
实施例16
化合物247的合成
除了起始原料更换为247-A、247-C和37-D以外,其他与实施例1相同。
1HNMR(DMSO):δ9.27(s,2H),8.85(d,2H),8.52(d,2H),8.30(d,2H),8.15(d,2H),8.13(d,2H),8.03(d,3H),7.90(d,2H),7.89(s,2H),7.83(s,1H),7.75(s,4H),7.68(m,2H),7.63(m,2H),7.36(d,1H),7.07(s,4H).
实施例17
化合物281的合成
除了起始原料更换为281-A和281-C以外,其他与实施例1相同。
1HNMR(DMSO):δ8.56(d,2H),8.46(s,2H),8.30(d,2H),8.11(d,2H),8.00(d,2H),7.96(d,2H),7.93(d,2H),7.89(s,2H),7.61(m,2H),7.59(m,2H),7.50(d,2H),7.07(s,4H).
实施例18
化合物320的合成
除了起始原料更换为320-A、320-C和5-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.03(d,2H),7.98(d,2H),7.82(d,2H),7.77(s,4H),7.54(d,2H),7.52(d,2H),7.39(m,2H),7.31(m,2H),7.18(d,2H),7.07(s,4H),1.69(s,6H).
实施例19
化合物356的合成
除了起始原料更换为356-A、356-B和181-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.45(d,2H),8.24(d,2H),8.20(s,2H),7.94(d,2H),7.93(d,2H),7.56(m,2H),7.49(m,2H),7.34(d,2H),7.29(s,2H),7.15(d,2H),7.07(s,4H).
实施例20
化合物403的合成
除了起始原料更换为403-A、403-C和18-D以外,其他与实施例1相同。
1HNMR(DMSO):δ7.74(m,4H),7.38(d,4H),7.35(d,2H),7.33(d,2H),7.29(s,2H),7.24(m,2H),7.07(s,4H),7.08(d,2H),7.00(m,1H).
实施例21
化合物425的合成
除了起始原料更换为425-A、425-B、425-C和5-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.03(d,2H),7.98(d,2H),7.82(d,2H),7.76(d,2H),7.60(s,2H),7.56(d,2H),7.54(d,2H),7.47(d,2H),7.31(m,2H),7.30(s,4H),1.69(s,4H).
实施例22
化合物460的合成
除了起始原料更换为460-A、460-C和5-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.03(d,2H),7.98(d,2H),7.82(d,2H),7.76(s,2H),7.54(d,2H),7.39(m,2H),7.37(m,2H),7.34(s,2H),7.31(d,4H),7.07(s,4H).
实施例23
化合物509的合成
除了起始原料更换为509-A、509-C和194-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.09(d,2H),8.06(d,2H),7.99(d,2H),7.96(d,4H),7.63(m,2H),7.60(m,2H),7.55(s,1H),7.39(d,2H),7.38(d,2H),7.33(d,2H),7.26(s,2H),7.25(d,4H),7.24(m,2H),7.07(s,4H),7.08(d,2H),7.00(m,1H).
实施例24
化合物553的合成
除了起始原料更换为553-A、553-B、553-C和63-D以外,其他与实施例18相同。
1HNMR(DMSO):δ9.51(s,2H),9.32(s,2H),8.52(d,2H),7.84(s,2H),7.76(s,4H),7.65(s,2H),7.63(d,2H),7.62(m,4H),7.58(m,2H),7.53(d,2H),7.50(d,4H),6.60(s,4H),1.69(s,12H).
实施例25
化合物573的合成
除了起始原料更换为573-A、425-B、573-C和18-D以外,其他与实施例1相同。
1HNMR(DMSO):δ7.74(m,4H),7.71(s,2H),7.59(s,2H),7.38(d,4H),7.33(d,2H),7.24(m,4H),7.23(s,2H),7.08(d,4H),7.00(m,2H),6.65(d,2H).
实施例26
化合物599的合成
除了起始原料更换为599-A、599-C和5-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.15(s,2H),8.08(d,2H),8.03(d,2H),7.98(d,2H),7.87(d,2H),7.82(d,2H),7.76(d,2H),7.54(d,2H),7.39(m,2H),7.31(m,2H),7.07(s,4H).
实施例27
化合物613的合成
除了起始原料更换为613-A、613-B、613-C和194-D以外,其他与实施例1相同。
1HNMR(DMSO):δ8.12(s,2H),8.09(d,2H),8.06(d,2H),7.99(d,2H),7.90(d,2H),7.63(m,2H),7.61(d,2H),7.60(m,2H),7.59(d,4H),7.55(s,2H),7.53(d,4H),7.38(d,2H),7.04(s,4H).
实施例28
薄膜样品的制作方法,具体如下:无碱玻璃基板首先进行20分钟的UV臭氧洗涤处理,然后放置于真空蒸镀装置内,进行排气,直到装置内的真空度达到1×10-3Pa的条件下,用电阻加热蒸镀法,以0.1纳米/s的蒸镀速度将化合物1加热蒸镀制备约厚度约为50纳米的薄膜。上述制备的薄膜样品折射率和衰减系数的测定使用仪器是椭圆偏振光谱(J.A.Woollam Co.Inc M-2000),※光学常数(折射率:n是小数点3位数四舍五入)。
实施例29
除了化合物5代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例30
除了化合物18代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例31
除了化合物37代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例32
除了化合物44代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价。评价结果见表1。
实施例33
除了化合物63代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例34
除了化合物73代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例35
除了化合物81代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例36
除了化合物90代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例37
除了化合物112代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例38
除了化合物141代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例39
除了化合物176代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例40
除了化合物181代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例41
除了化合物194代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价。评价结果见表1。
实施例42
除了化合物228代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例43
除了化合物247代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,评价结果见表1。
实施例44
除了化合物281代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例45
除了化合物320代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例46
除了化合物356代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例47
除了化合物403代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例48
除了化合物425代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例49
除了化合物460代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例50
除了化合物509代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例51
除了化合物553代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例52
除了化合物573代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例53
除了化合物599代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
实施例54
除了化合物613代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
比较例1
除了SMD1代替化合物1以外,其余与实施例28相同。对有机发光器件进行评价,结果见表1。
表1
由表1所示可知,采用本发明的有机化合物,有机发光器件的折射率相较于SMD1有较大的提升。
实施例55
首先用超声波清洗仪,使用异丙醇洗涤无碱玻璃15分钟,然后在空气中进行30分钟UV臭氧洗涤处理。处理好的基板利用真空蒸镀法,首先蒸镀铝100纳米作为阳极,然后在阳极上蒸镀空穴注入层(HATCN,50纳米),空穴传输层(NPD,30纳米),蓝色发光层(主体ADN和掺杂BD(重量比95:5,30纳米),电子传输层(Alq3:Liq3=1:1,30纳米),电子注入层(LiF,0.5纳米)依次层叠蒸镀后,共蒸镀Mg:Ag金属(重量比10:1,15纳米)作成半透明阴极。然后蒸镀化合物1(60纳米)作为覆盖层。最后在氮气氛围下利用环氧树脂粘合剂封装封发光器件。
发光器件的测试方法为:上述发光器件在室温,大气中,用10毫安每平方米直流电流,分光放射辉度计(CS1000,柯尼卡美能达株式会社)测试封口板的发光性能。测试得到发光效率为7.4cd/A,色纯度为CIE(x,y)=(0.139,0.051),使用化合物1作为覆盖层得到高发光效率,高色纯度的高性能发光元件,测试结果见表2。
实施例56
除了覆盖层材料为化合物5以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例57
除了覆盖层材料为化合物18以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例58
除了覆盖层材料为化合物37以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例59
除了覆盖层材料为化合物44以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例60
除了覆盖层材料为化合物63以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例61
除了覆盖层材料为化合物73以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例62
除了覆盖层材料为化合物81以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例63
除了覆盖层材料为化合物90以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例64
除了覆盖层材料为化合物112以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例65
除了覆盖层材料为化合物141以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例66
除了覆盖层材料为化合物176以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例67
除了覆盖层材料为化合物181以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例68
除了覆盖层材料为化合物194以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例69
除了覆盖层材料为化合物228以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例70
除了覆盖层材料为化合物247以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例71
除了覆盖层材料为化合物281以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例72
除了覆盖层材料为化合物320以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例73
除了覆盖层材料为化合物356以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例74
除了覆盖层材料为化合物403以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例75
除了覆盖层材料为化合物425以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例76
除了覆盖层材料为化合物460以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例77
除了覆盖层材料为化合物509以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例78
除了覆盖层材料为化合物553以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例79
除了覆盖层材料为化合物573以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例80
除了覆盖层材料为化合物599以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
实施例81
除了覆盖层材料为化合物613以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
比较例2
除了覆盖层材料为NPD以外,其余与实施例55制作相同的元件进行评价,测试结果见表2。
比较例3
除了覆盖层材料为TBDB以外,其余与实施例55制作相同的元件进行评价,评价结果见表2。
表2
从表2所示可知,本发明的有机化合物用于OLED发光器件,与比较例2、比较例3相比,光取出得到了显著的提升,在相同电流密度下,器件效率得到了提升。同时,由于OLED发光器件的效率得到了提升,在同等亮度的功耗下发光器件的寿命也得以提升。另外,本发明的化合物作为覆盖层材料应用于OLED发光器件,能够得到高色纯度的发光器件,更加适合于工业商业应用。
以上测试结果得出,本发明的化合物适用于有机发光器件材料,能够同时得到高发光效率和高色纯度得发光器件,更适用于OLED发光器件。
以上所述,仅为本发明较佳的具体实施方式,但本发明的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明揭露的技术范围内,根据本发明的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明的保护范围之内。
Claims (11)
1.一种有机化合物,其具有下式(1)所示的结构:
式(1)中,X1和X2相同或不相同,独立选自单键、O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-;
X3和X4相同或不相同,独立选自O、S、-SO2-、-SO-、-CR8R9-、-NR10-、-SiR11R12-、-SeR13R14-;
Ar1和Ar2相同或不相同,独立选自如下任一个取代基团:
其中,Ar3、Ar4和Ar5独立选自取代或未取代的C6-C60芳基,且Ar3不为苯基;
X5选自O、S、-NR15-、-CR16R17-;
R1-R17相同或不相同,独立选自氢、氘、氰基、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C1-C60杂烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环;
*表示取代基的连接位置。
2.根据权利要求1所述的有机化合物,其特征在于,X3和X4相同,且Ar1和Ar2相同。
3.根据权利要求1所述的有机化合物,其特征在于,Ar3为萘基。
4.根据权利要求1所述的有机化合物,其特征在于,X1和X2相同,选自O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-,其中R1-R7独立选自氢、氘、氰基、甲基、苯基、萘基、吡啶基或者与临近的原子键合成环。
5.根据权利要求1所述的有机化合物,其特征在于,X1和X2不同,X1选自单键、O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-,X2选自O、S、-SO2-、-SO-、-CR1R2-、-NR3-、-SiR4R5-、-SeR6R7-,其中R1-R7独立选自氢、氘、氰基、甲基、苯基、萘基、吡啶基或者与临近的原子键合成环。
7.一种有机材料,包括权利要求1-6任一项所述有机化合物中的一种或多种。
8.一种有机发光器件,包括权利要求1-6任一项所述的有机化合物中的一种或多种、或者权利要求7所述的有机材料。
9.根据权利要求8所述的有机发光器件,其特征在于,
包括基板、第一电极、包含发光层在内的一层以上有机层和第二电极元件;
还包含覆盖层,所述覆盖层材料含有权利要求1-6任一项所述有机化合物中的一种或多种、或者权利要求7所述的有机材料。
10.根据权利要求8或9所述的有机发光器件,其特征在于,所述有机发光器件包括有机光伏器件、有机电致发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
11.显示或照明装置,其特征在于,其包括权利要求8-10任一项所述的有机发光器件。
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