CN107344923A - 电场发光装置的有机化合物 - Google Patents
电场发光装置的有机化合物 Download PDFInfo
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Abstract
本发明提供一种由下式(1)表示的有机化合物,其中A、m和R1至R3与本发明中所述的定义相同。使用该有机化合物作为荧光发射客体的有机EL装置,以深蓝色呈现(CIEy=0.09~0.12),并展现绝佳的功效。
Description
【技术领域】
本发明是关于使用有机材料的有机化合物和有机电场发光(有机EL)装置。具体而言,本发明提供具有通式(1)的有机化合物,使用该有机化合物作为发光层的荧光发光客体的有机EL装置。
【背景技术】
有机电场发光(有机EL)为发光二极管(LED),其中发射层为因呼应电流而发光的有机化合物所制成的薄膜。有机化合物的发射层夹在两个电极之间。有机EL因其高照度、低重量、超薄外形、无背光的自照明、低功耗、宽视角、高对比度度、制造简单、快速反应时间而应用于平板显示器中。
有机材料电场发光的首次发现于1950年代早期,由安德烈贝诺斯(AndreBernanose)与其同事于法国南锡大学所发现。马丁伯普(Martin Pope)与其纽约大学的同事,于1963年在真空下掺杂有稠四苯蒽的单一纯晶体上,首次观察到直流(DC)电场发光。
第一个二极管装置,是由在伊士曼柯达(Eastman Kodak)的邓青云(ChingW.Tang)和史蒂芬凡斯莱克(Steven Van Slyke)于1987年所提出。该装置采用具有单独的电洞传输和电子传输层的双层结构,可导致降低操作电压并提高效率,这促成当今主流的有机EL研究和装置生产方式。
一般而言,有机EL装置由位于两个电极间的有机材料层组成,其包括电洞传输层(HTL)、发射层(EML)、电子传输层(ETL)。有机EL的基本机制包括载子注入、载子传输、复合以及形成发光的激子。当外部电压施加到有机EL装置时,电子和电洞将分别自阴极和阳极注入,电子将从阴极注入最低未占用分子轨域(lowest unoccupied molecular orbital,LUMO)中,电洞将从阳极注入最高占用分子轨域(highest occupied molecular orbital,HOMO)中。当电子与发光层中的电洞复合时,将会形成激子然后发光。当发光分子吸收能量来达到激发态时,根据电子和电洞自旋组合方式,激子可处于单重或三重态。75%的激子藉由电子和电洞的重组形成而达到三重激发态。从三重态衰减是自旋禁阻(self forbidden)的,因此,荧光电场发光装置仅具有25%的内量子效率。与荧光电场发光装置相反,磷光有机EL装置利用自旋轨道相互作用,来促进单重态和三重态间的跨系统交叉,从而获得单重态和三重态的发射,以及电场发光装置的内部量子效率从25%至100%。
对于主动式有机发光二极管(AMOLED)的全色平板显示器,使用于荧光发射层的材料在半衰期、效率、驱动电压方面仍无法令人满意。于本发明中,为了延长使用于有机EL装置发光层中荧光客体的半衰期、并降低驱动电压的目的,我们使用茚并三亚苯基─蒽基骨架连接到咔唑基、二苯并噻吩基、二苯并呋喃基、二芳基胺基、和其它供体基反应来完成通式(1)表示的有机化合物。有机化合物显示出有机EL装置的良好热稳定性和电荷载子迁移率。用于有机EL装置的JP2013232520、KR20120072784、WO2008062636、WO2012091471、US8962160B2、US8993130B2、US9040174B2、US9048437B2、和20140175383A1中揭露的基于茚并三亚苯基骨架的衍生物。没有现有技术证明茚并三亚苯─蒽骨架链,与用作有机EL装置的荧光发光客体的咔唑基、二苯并噻吩基、二苯并呋喃基、二芳基胺基、和其它供体基相连。
根据上述原因,本发明的目的为解决现有技术的这些问题,并提供一种热稳定性、高发光效率、高亮度、和长半衰期的发光装置。本发明公开了具有通式(1)的有机材料,用作荧光发射客体材料,并具有良好电荷载子迁移率和优秀的操作耐久性,可降低驱动电压和功率消耗、增加有机EL装置效率和半衰期。
【发明内容】
本发明提供一种有机化合物与其用于有机EL装置发光层的荧光客体的用途。该有机化合物可克服传统材料的缺点,如:较短的半衰期、更低的效率、更高的驱动电压。
本发明的目的为将有机化合物用作有机EL装置的荧光发光客体,并且可降低驱动电压、降低功耗并提高效率。
本发明具有工业生产的经济优点。因此,本发明提供可用于有机EL装置的有机化合物,其中有机化合物由下式(1)表示:
其中A代表式(2)至式(5)其中之一:
其中m表示0至10的整数,n表示0或1的整数,X是选自原子或选自O、S和NR7的原子的二价桥,Y是选自原子或由O、S、C(R8)(R9)、Si(R10)(R11)和NR12组成的群组、Ar1和Ar2表示具有6至30个碳原子的取代或未取代的芳基,R1至R12独立地选自由以下组成的群组:氢原子、卤素、取代或未取代的碳原子数为1~30的烷基、取代或未取代的碳原子数为6~30的芳基、和取代或未取代的碳原子数为6~30的芳烷基。
上列详细说明系针对本发明的一可行实施例的具体说明,惟该实施例并非用以限制本发明的专利范围,凡未脱离本发明技艺精神所为的等效实施或变更,均应包含于本案的专利范围中。
综上所述,本案不但在空间型态上确属创新,并能较现有产品增进上述多项功效,应已充分符合新颖性及创造性的法定发明专利要件,爰依法提出申请。
【附图说明】
图1为本发明的电场发光装置的有机化合物的实施例的有机EL装置的示意图。
【本代表图的符号简单说明】:
6 透明电极
7 电洞注入层
8 电洞传输层
9 电子阻挡层
10 发射层
11 电子传输层
12 电子注入层
13 金属电极
【具体实施方式】
为利贵审查员了解本发明的技术特征、内容与优点及其所能达到的功效,兹将本发明配合附图,并以实施例的表达形式详细说明如下,而其中所使用的图式,其主旨仅为示意及辅助说明书之用,未必为本发明实施后的真实比例与精准配置,故不应就所附的图式的比例与配置关系解读、局限本发明于实际实施上的权利范围,合先叙明。
在本发明的第一实施实施例中,揭露了可用作有机EL装置荧光发光客体的有机化合物。所提及的衍生物由下式(1)表示:
其中A代表式(2)至式(5)其中之一:
其中m表示0至10的整数,n表示0或1的整数,X是选自原子或选自O、S和NR7的原子的二价桥,Y是选自原子或由O、S、C(R8)(R9)、Si(R10)(R11)和NR12组成的群组、Ar1和Ar2表示具有6至30个碳原子的取代或未取代的芳基,R1至R12独立地选自由以下组成的群组:氢原子、卤素、取代或未取代的碳原子数为1~30的烷基、取代或未取代的碳原子数为6~30的芳基、和取代或未取代的碳原子数为6~30的芳烷基。
于本实施例中,部分有机化合物如下所示:
本发明中有机化合物的详细制备可通过示例性实施方案来阐明,但是本发明不限于示例性实施方案。实施例1~7显示本发明中有机化合物的实施例的制备。实施例8显示有机EL装置的制造和I-V-B、有机EL装置测试报告的半衰期。
实施例1
化合物1的合成
2-(联苯-2-基)-7-溴-9,9-二甲基-9H-芴(2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene)的合成
将35.2g(100mmol)的2,7-二溴-9,9-二甲基-9H-芴(2,7-dibromo-9,9-dimethyl-9H-fluorene)、21.8g(110mmol)的联苯-2-基硼酸(biphenyl-2-ylboronic acid)、2.31g(2mmol)的Pd(PPh3)4、将75ml 2M Na2CO3、150ml EtOH的混合物和300ml甲苯脱气,并置于氮气下,然后在100℃加热12小时。反应完成后,使混合物冷却至室温。有机层用乙酸乙酯(ethyl acetate)和水萃取,用硫酸镁干燥,除去溶剂,通过以硅胶柱色谱来纯化残余物,得到黄色固体状的产物(26.8g,63.0mmol,63%)。
12-溴-10,10-二甲基-10H-茚并[2,1-b]三亚苯(12-bromo-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)的合成
在脱气并充满氮气的3000ml三颈烧瓶中,将26.8g(60mmol)的2-(联苯-2-基)-7-溴-9,9-二甲基-9H-芴(2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene)溶于无水二氯甲烷(1500ml)中,然后加入97.5g(600mmol)的氯化铁(III)(Iron(III)chloride),将混合物搅拌1小时。于混合物中加入500ml的甲醇,并分离有机层,以真空方式除去溶剂。残余物通过硅胶柱色谱(己烷-二氯甲烷)得到白色固体(10.7g,25.3mmol,40%)。1H NMR(CDCl3,400MHz):化学位移(ppm)8.95(s,1H),8.79~8.74(m,2H),8.69~8.68(m,3H),7.84(d,J=8.0Hz,1H),7.72~7.65(m,5H),7.57(d,J=8.0Hz,1H),1.66(s,6H)。
2-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)的合成
将10.7g(25.3mmol)的12-溴-10,10-二甲基-10H-茚并[1,2-b]三亚苯(12-bromo-10,10-dimethyl-10H-indeno-[1,2-b]triphenylene),7.7g(30.3mmol)的双(频哪醇)二硼(bis(pinacolato)diboron),0.3g(0.26mmol)的Pd(PPh3)4,7.4g(75.4mmol)的乙酸钾(potassium acetate)混合物,并将300ml的1,4-二恶烷(1,4-dioxane)脱气并置于氮气下,然后在90℃加热16小时。反应完成后,使混合物冷却至室温。分离有机相并用乙酸乙酯(ethyl acetate)和水洗涤。以硫酸镁(magnesium sulfate)干燥后,真空除去溶剂。残余物通过硅胶柱色谱(己烷-二氯甲烷)纯化,得到浅黄色固体产物(6.4g,13.7mmol,54%);1HNMR(CDCl3,400MHz):化学位移(ppm)9.03(s,1H),8.81(d,J=7.84Hz,1H),8.77(d,J=7.88Hz,1H),8.70~8.67(m,3H),8.02~7.93(m,3H),7.71~7.67(m,4H),1.69(s,6H),1.42(s,12H)。
12-(蒽-9-基)-10,10-二甲基-10H-茚并[2,1-b]三亚苯(12-(anthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)的合成
将4.7g(10mmol)的2-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane),2.8g(11mmol)的9-溴蒽(9-bromoanthracene),0.22g(0.2mmol)的四(三苯基膦)钯(tetrakis(triphenylphosphine)palladium),20ml 2M Na2CO3,20ml EtOH的混合物,和50ml的甲苯(toluene)的混合物脱气,置于氮气下,然后在90℃加热过夜。反应完成后,使混合物冷却至室温。之后加入150ml的MeOH,同时进行搅拌,并抽吸滤出沉淀的产物。得到3.5g(产率67%)黄色产物,将其从甲苯中再结晶。
12-(10-溴蒽-9-基)-10,10-二甲基-10H-茚并[2,1-b]三亚苯(12-(10-bromoanthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)的合成
将得到的12-(蒽-9-基)-10,10-二甲基-10H-茚并[2,1-b]三亚苯(12-(anthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)(3.5g)和DMF(35ml)加入反应容器中。在冰冷却的条件下,加入N-溴代琥珀酰亚胺(N-bromosuccinimide)(1.5g),将混合物搅拌9小时。加入水(350ml),有机层用二氯甲烷和水萃取,以无水硫酸镁(anhydrous magnesium sulfate)干燥,除去溶剂,残余物通过硅胶柱色谱(己烷-二氯甲烷)纯化,得到浅黄色固体产物(3.1g,5.2mmol,78%)。
3-(10-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)蒽-9-基)-9-苯基-9H-咔唑(3-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)-9-phe nyl-9H-carbazole)的合成
将3.1g(5.2mmol)的12-(10-溴蒽-9-基)-10,10-二甲基-10H-茚并[2,1-b]三亚苯(12-(10-bromoanthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene),2.2g(6mmol)的9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),0.22g(0.2mmol)的四(三苯基膦)钯(tetrakis(triphenylphosphine)palladium),20ml 2MNa2CO3,20ml EtOH的混合物和50ml的甲苯(toluene)脱气并置于氮气下,然后在110℃加热过夜。反应完成后,使混合物冷却至室温。之后加入150ml的MeOH,同时进行搅拌,并抽吸滤出沉淀的产物。得到2.6g(产率67%)黄色产物,将其从甲苯中再结晶。MS(m/z,FAB+):761.4,1H NMR(CDCl3,400MHz):化学位移(ppm)9.11(s,1H),8.87(d,J=7.84Hz,1H),8.80~8.75(m,2H),8.71~8.69(m,2H),8.28(d,J=7.84Hz,1H),8.22~8.11(m,2H),7.88~7.82(m,4H),7.76~7.63(m,10H),7.61~7.44(m,5H),7.39~7.28(m,5H),1.74(s,6H)。
实施例2
化合物6的合成
10-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)-N-苯基-N-间甲苯基蒽-9-胺(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-N-phenyl-N-m-tolylant hracen-9-amine)的合成
将6.0g(10mmol)的12-(10-溴蒽-9-基)-10,10-二甲基-10H-茚并[2,1-b]三亚苯(12-(10-bromoanthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene),3g(15.1mmol)的3-甲基-N-苯基苯胺(3-methyl-N-phenylaniline),0.05g(0.2mmol)的乙酸钯(II)(palladium(II)acetate),0.15g(0.4mmol)的2-(二环己基膦基)联苯(2-(dicyclohexylphosphino)biphenyl),2g(20mmol)的叔丁醇钠(sodium tert-butoxide)的混合物和100ml的邻二甲苯(O-xylene)的混合物回流过夜。反应完成后,将溶液在100℃下过滤,以得到滤液,将滤液加入1L的MeOH中,同时进行搅拌,并将沉淀的产物抽滤。得到3.1g(产率45%)黄色产物,将其从甲苯中再结晶。MS(m/z,FAB+):701.6。
实施例3
化合物12的合成
N-(2-氯苯基)-9,9-二甲基-9H-芴-2-胺(N-(2-chlorophenyl)-9,9-dimethyl-9H-fluoren-2-amine)的合成
将6.9g(25.3mmol)的2-溴-9,9-二甲基-9H-芴(2-bromo-9,9-dimethyl-9H-fluorene),3.2g(25.3mmol)的2-氯苯胺(2-chloroaniline),0.11g(0.5mmol)的乙酸钯(II)(palladium(II)acetate),0.55g(1.0mmol)的1,1-双(二苯基膦基)二茂铁(1,1-bis(diphenyl-phosphino)ferrocene),4.85g(50.6mmol)的叔丁醇钠(sodium tert-butoxide)混合物和100ml甲苯(toluene)脱气,置于氮气下,然后在110℃加热过夜。反应完成后,使混合物冷却至室温。分离有机相并用乙酸乙酯和水洗涤。以硫酸镁干燥后,真空除去溶剂。残余物通过硅胶柱色谱(己烷-二氯甲烷)纯化,得到浅黄色固体产物(4.9g,18.0mmol,71%)。
3,3-二甲基-1,3-二氢茚并[2,1-b]咔唑(3,3-dimethyl-1,3-dihydroindeno[2,1-b]carbazole)的合成
将4.9g(18.0mmol)的N-(2-氯苯基)-9,9-二甲基-9H-芴-2-胺(N-(2-chlorophenyl)-9,9-dimethyl-9H-fluoren-2-amine),0.4g(1.6mmol)的乙酸钯(II)(palladium(II)acetate),75ml的新戊酸(pivalic acid),将0.8g的碳酸钾(6mmol)(potassium carbonate)和240ml的1-甲基-2-吡咯烷酮(1-methyl-2-pyrrolidone)的混合物脱气并置于氮气下,然后在130℃加热24小时。反应完成后,使混合物冷却至室温。有机层用二氯甲烷(dichloromethane)和水萃取,以无水硫酸镁(anhydrous magnesium sulfate)干燥,除去溶剂,残余物从己烷(hexane)和二氯甲烷(dichloromethane)中再结晶,得到产物(2.1g,7.4mmol,产率41%)。
3,3-二甲基-1-苯基-1,3-二氢茚并[2,1-b]咔唑(3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole)的合成
将4.9g(18mmol)的3,3-二甲基-1,3-二氢茚并[2,1-b]咔唑(3,3-dimethyl-1,3-dihydroindeno[2,1-b]carbazole),3.4g(21.6mmol)的溴苯(bromobenzene),0.1g(0.4mmol)的乙酸钯(II)(palladium(II)acetate),将0.3g(0.8mmol)的2-(二环己基膦基)联苯(2-(dicyclohexylphosphino)biphenyl),4g(40mmol)的叔丁醇钠(sodium tert-butoxide)的混合物和50ml的邻二甲苯(o-xylene)在氮气下回流过夜。反应完成后,将溶液在100℃下过滤以接收滤液,将滤液加入1L的MeOH中,同时进行搅拌,并将沉淀的产物抽吸过滤。得到(4.1g,11.5mmol,64%)黄色产物,将其从甲苯中再结晶。
10-溴-3,3-二甲基-1-苯基-1,3-二氢茚并[2,1-b]咔唑(10-bromo-3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole)的合成
将得到的3,3-二甲基-1-苯基-1,3-二氢茚并[2,1-b]咔唑(3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole)(4.1g)和DMF(40ml)加入到反应容器中。于冰冷却的条件下加入N-溴代琥珀酰亚胺(N-bromosuccinimide)(2g),将混合物搅拌6小时,然后静置一夜。加入400ml水,有机层用二氯甲烷(dichloromethane)和水萃取,用无水硫酸镁(anhydrous magnesium sulfate)干燥,除去溶剂,残余物通过硅胶柱色谱(己烷-二氯甲烷)纯化,得到产物(2.9g,6.7mmol,72%)。
3,3-二甲基-1-苯基-10-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-1,3-二氢茚并[2,1-b]咔唑(3,3-dimethyl-1-phenyl-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihy droindeno[2,1-b]carbazole)的合成
将2.9g(6.7mmol)的10-溴-3,3-二甲基-1-苯基-1,3-二氢茚并[2,1-b]咔唑(10-bromo-3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole),2.2g(8.67mmol)的双(频哪醇)二硼(bis(pinacolato)diboron),0.36g(0.32mmol)的四(三苯基膦)钯(tetrakis(triphenylphosphine)palladium),2g(20.28mmol)的乙酸钾(potassiumacetate)的混合物和300ml的1,4-二恶烷(1,4-dioxane)脱气,置于氮气下,然后在120℃加热16小时。反应完成后,使混合物冷却至室温。有机层用乙酸乙酯(ethyl acetate)和水萃取,以无水硫酸镁(anhydrous magnesium sulfate)干燥,除去溶剂,产物通过使用己烷(hexanes)和乙酸乙酯(ethyl acetate)的混合物,作为洗脱剂的柱纯化,得到2.4g浅黄色产物(产率76%)。
10-(10-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)蒽-9-基)-3,3-二甲基-1-苯基-1,3-二氢茚并[2,1-b]咔唑(10-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)-3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole)的合成
将5g(5mmol)的12-(10-溴蒽-9-基)-10,10-二甲基-10H-茚并[2,1-b]三亚苯(12-(10-bromoanthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene),2.4g(5mmol)的3,3-二甲基-1-苯基-10-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-1,3-二氢茚并[2,1-b]咔唑(3,3-dimethyl-1-phenyl-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihy droindeno[2,1-b]carbazole),0.22g(0.2mmol)的四(三苯基膦)钯(tetrakis(triphenyl phosphine)palladium),20ml 2M Na2CO3,20ml EtOH的混合物和50ml的甲苯(toluene)的混合物脱气,置于氮气下,然后在110℃加热过夜。反应完成后,使混合物冷却至室温。之后加入150ml的MeOH,同时进行搅拌,并抽吸滤出沉淀的产物。得到2.6g(产率67%)黄色产物,将其从甲苯中再结晶。MS(m/z,FAB+):877.6,1H NMR(CDCl3,400MHz):化学位移(ppm)9.13(s,1H),8.85(d,J=7.84Hz,1H),8.78~8.74(m,2H),8.73~8.68(m,2H),8.28~8.24(m,3H),8.22~8.11(m,2H),7.88~7.82(m,4H),7.76~7.63(m,10H),7.62~7.43(m,5H),7.38~7.28(m,5H),1.74(s,6H),1.57(s,6H)。
实施例4
化合物17的合成
2-(10-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)蒽-9-基)二苯并[b,d]呋喃(2-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)dibenz o[b,d]furan)的合成
二苯并[b,d]呋喃-2-基硼酸(Dibenzo[b,d]furan-2-ylboronic acid)代替9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-9H-咔唑(9-phenyl -3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),使用与合成实施实施例1相同的方法,获得化合物17的所需化合物(1.4g,产率=57%)。MS(m/z,FAB+):686.3。
实施例5
化合物18的合成
4-(10-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)蒽-9-基)二苯并[b,d]噻吩(4-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)dibenzo[b,d]thiophene)的合成
二苯并[b,d]噻吩-4-基硼酸(Dibenzo[b,d]thiophen-4-ylboronic acid)代替9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),使用与合成实施实施例1中相同的方法,获得化合物18的所需化合物(1.8g,产率=68%)。MS(m/z,FAB+):720.8。
实施例6
化合物19的合成
4-(10-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)蒽-9-基)二苯并[b,d]噻吩(4-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)dibenz o[b,d]thiophene)的合成
二苯并[b,d]噻吩-4-基硼酸(Dibenzo[b,d]thiophen-4-ylboronic acid)代替9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),使用与合成实施例1中相同的方法,获得化合物19的所需化合物(1.8g,产率=68%)。MS(m/z,FAB+):720.8。
实施例7
化合物20的合成
4-(10-(10,10-二甲基-10H-茚并[2,1-b]三苯基-12-基)蒽-9-基)二苯并[b,d]呋喃(4-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)dibenz o[b,d]furan)的合成
二苯并[b,d]呋喃-4-基硼酸(Dibenzo[b,d]furan-4-ylboronic acid)代替9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),使用与合成实施实施例1中相同的方法,获得化合物20的所需化合物(2.6g,产率=53%)。MS(m/z,FAB+):686.4。
生产有机EL装置的一般方法
提供具有9~12奥姆/平方的电阻、120~160nm厚度的ITO涂装的玻璃(以下称为ITO基材),并在超声波浴(例如:清洁剂、去离子水)中进行清洁。在有机层的气相沉积之前,通过UV和臭氧进一步处理经清洁后的ITO基材。ITO基材的所有预处理流程,都在净化室(100级)下进行。
通过气相沉积在高真空单元(10-7Torr),将这些有机层按顺序施加至ITO基材上,例如:电阻加热的石英舟。借助于石英晶体监测器来精确地监测、或设置各层的厚度和气相沉积速率(0.1~0.3nm/sec)。如上所述,单个层也可以由一种以上的化合物所组成,例:通常是掺杂有掺杂剂材料的主体材料。这可通过两个或更多个来源的共蒸发来实现。
二吡嗪并[2,3-f:2,3]喹喔啉-2,3,6,7,10,11-六腈(Dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitrile,HAT-CN)用作该有机EL装置中的电洞注入层,N,N-双(萘-1-基)-N,N-双(苯基)-联苯胺(N,N-Bis(naphthalene-1-yl)-N,N-bis(phenyl)-benzidine,NPB)被最广泛地用作电洞传输层;在有机EL装置中使用10,10-二甲基-12-(10-(4-(萘-1-基)苯基)蒽-9-基)-10H-茚并[2,1-b]三亚苯(H3)(10,10-dimethyl-12-(10-(4-(naphthalene-1-yl)phenyl)anthracen-9-yl)-10H-ind eno[2,1-b]triphenylene)和10,10-二甲基-13-(10-(3-(萘-2-基)苯基)蒽-9-基)-10H-茚并[2,1-b]三亚苯(H4)(10,10-dimethyl-13-(10-(3-(naphthalen-2-yl)phenyl)anthracen-9-yl)-10H-inde no[2,1-b]triphenylene)作为发射主体,N1,N1,N6,N6-四-甲苯基芘-1,6-二胺(D1)(N1,N1,N6,N6-tetram-tolylpyrene-1,6-diamine)作为蓝色客体并使用于比较用途;HB3(参见下面的化学结构)用作电洞阻挡材料(HBM)和1-(4-(10-(萘-2-基)蒽-9-基)苯基)-2-苯基-1H-苯并[d]咪唑(ET2)(1-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imi dazole)用作电子传输材料,以在有机EL装置中与8-羟基喹啉锂(8-hydroxyquinolato-lithium,LiQ)共沉淀。用于产生标准有机EL装置控制组的现有技术的OLED材料,和本发明中比较性材料的化学结构如下:
典型的有机EL装置由低功函数金属所组成,如:Al,Mg,Ca,Li和K,藉由热蒸发来作为阴极,低功函数金属可帮助从阴极注入电子传输层的电子。此外,为了减少电子注入阻障,并且改善有机EL装置的性能,在阴极与电子传输层之间导入薄膜电子注入层。电子注入层的传统材料为具有低功函数的金属卤化物或金属氧化物,例如:LiF、LiQ、MgO、或Li2O.。
另一方面,于有机EL装置制造后,可使用PR650光谱扫描光谱仪来测量EL光谱和CIE坐标。此外,使用Keithley 2400可编程设计电压-电流源,来获得电流/电压、发光/电压以及良率/电压等特性。上述提及的设备可在室温(约25℃)下,并且于大气压力下进行操作。
实施例8
使用与上述一般方法类似的方法,制作具有以下器件结构的荧光发射有机EL装置(参见图1),其中具有透明电极6及金属电极13,及金属电极13之间具有机依序沉积至透明电极6上的电洞注入层7、电洞传输层8,沉积到电洞传输层8上的电子阻挡层9,沉积到电子阻挡层9上的荧光或磷光发射层10,沉积到发射层10上的电子传输层11,沉积到电子传输层11上的电子注入层12。装置:ITO/HAT-CN(20nm)/NPB(110nm)/发射主体掺杂5%发光客体(30nm)/HB3/ET2掺杂50%LiQ(35nm)/LiQ(1nm)/Al(160nm)。发射荧光的有机EL装置测试报告的I-V-B(1000尼特(nit)下)和半衰期时间如表1所报导。半衰期时间被定义为1000cd/m2的初始亮度降到一半的时间。
表1
在上述有机EL装置试验报告(参见表1)的优选实施方案中,我们显示于本发明中用作有机EL的发光客体材料通式(1)的有机化合物,能显示出良好的性能。更具体而言,本发明中的有机EL装置使用具有通式(1)的有机化合物,作为发光客体材料,以及例如:H3和H4的发光主体材料配位,来表现出更低的功耗、更高的效率和更长的半衰期。
总而言之,本发明揭露了一种用作有机EL装置的发光客体材料通式(1)的有机化合物。所述有机化合物由下式(1)表示:
本发明具有工业生产的经济优点。因此,本发明提供可用于有机EL装置的有机化合物,其中有机化合物由下式(1)表示:
其中A代表式(2)至式(5)其中之一:
其中m表示0至10的整数,n表示0或1的整数,X是选自原子或选自O、S和NR7的原子的二价桥,Y是选自原子或由O、S、C(R8)(R9)、Si(R10)(R11)和NR12组成的群组、Ar1和Ar2表示具有6至30个碳原子的取代或未取代的芳基,R1至R12独立地选自由以下组成的群组:氢原子、卤素、取代或未取代的碳原子数为1~30的烷基、取代或未取代的碳原子数为6~30的芳基、和取代或未取代的碳原子数为6~30的芳烷基。
综上所述,本案不仅于技术思想上确属创新,并具备现有的传统方法所不及的上述多项功效,已充分符合新颖性及创造性的法定发明专利要件,爰依法提出申请,恳请贵局核准本件发明专利申请案,以励发明,至感德便。
Claims (9)
1.一种具有通式(1)的有机化合物如下:
其中A代表式(2)至式(5)其中之一:
其中m表示0至10的整数,n表示0或1的整数,X是选自原子或选自O、S和NR7的原子的二价桥,Y是选自原子或由O、S、C(R8)(R9)、Si(R10)(R11)和NR12组成的群组、Ar1和Ar2表示具有6至30个碳原子的取代或未取代的芳基,R1至R12独立地选自由以下组成的群组:氢原子、卤素、取代或未取代的碳原子数为1~30的烷基、取代或未取代的碳原子数为6~30的芳基、和取代或未取代的碳原子数为6~30的芳烷基。
2.如权利要求1所述的有机化合物,其中该有机化合物进一步选自:
3.一种有机电激发光装置,其包括由阴极和阳极组成的一对电极对,其中该对电极对之间至少包含一层发光层、复数个有机薄膜层,其中该发光层包含如权利要求1所述的有机化合物。
4.如权利要求3所述的有机电激发光装置,其中该发光层是由如权利要求1项所述的有机化合物作为客体材料。
5.如权利要求3所述的有机电激发光装置,其中该发光层是由如权利要求1所述的有机化合物作为荧光发射客体材料。
6.如权利要求3所述的有机电激发光装置,其中该发光层发射蓝色荧光。
7.如权利要求3所述的有机电激发光装置,其中该有机电激发光装置为有机发光装置(organic light emitting device,OLED)。
8.如权利要求3所述的有机电激发光装置,其中该有机电激发光装置为照明面板。
9.如权利要求3所述的有机电激发光装置,其中该有机电激发光装置为背光面板。
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