CN110903305A - 一种磷光化合物和使用该化合物的有机发光二极管器件 - Google Patents
一种磷光化合物和使用该化合物的有机发光二极管器件 Download PDFInfo
- Publication number
- CN110903305A CN110903305A CN201910807578.0A CN201910807578A CN110903305A CN 110903305 A CN110903305 A CN 110903305A CN 201910807578 A CN201910807578 A CN 201910807578A CN 110903305 A CN110903305 A CN 110903305A
- Authority
- CN
- China
- Prior art keywords
- phosphorescent compound
- light emitting
- phosphorescent
- independently selected
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Abstract
Description
技术领域
本发明涉及一种磷光化合物和使用该化合物的有机发光二极管器件,更具体而言,涉及一种具有优异的色纯度和高亮度及发光效率的可溶的磷光主体化合物以及使用该化合物的OLED器件。
背景技术
近来,对于平板显示器(例如液晶显示器和等离子显示面板)的需求在增加。但是,这些平板显示器与阴极射线管(CRT)相比具有较低的响应时间和较窄的视角。
有机发光二极管(OLED)器件是能够解决以上问题并占地较小的下一代平板显示器之一。
OLED器件的元件可以在柔性基板(例如塑料基板)上形成。另外,OLED器件在视角、驱动电压、能耗和色纯度方面具有优势。侧外,OLED器件足以产生全色图像。
通常,OLED器件的发光二极管包括阳极、空穴注入层(HIL)、空穴输送层(HTL)、发光材料层(EML)、电子输送层(ETL)、电子注入层(EIL)和阴极。
OLED器件通过以下方式发光:由作为电子注入电极的阴极和由作为空穴注入电极的阳极分别将电子和空穴注入发光化合物层中,从而使电子与空穴复合以产生激子,并使激子由激发态跃迁至基态。
发光原理可以分为荧光发光和磷光发光。在荧光发光中,单线态激发状态的有机分子跃迁至基态,由此发出光。另一方面,在磷光发光中,三线态激发状态的有机分子跃迁至基态,由此发出光。
当发光材料层发射对应于能带隙的光时,具有0自旋的单线态激子和具有1自旋的三线态激子以1:3的比例产生。有机材料的基态为单线态,这使单线态激子可以跃迁至基态并伴随发光。但是,由于三线态激子不能发生伴随发光的跃迁,因此使用荧光材料的OLED器件的内量子效率被限制在25%以内。
另一方面,如果自旋轨道耦合动量很高,则单线态和三线态混合以使得在单线态和三线态之间产生系间跨越,并且三线态激子也可以跃迁至基态并伴随发光。磷光材料可以使用三线态激子和单线态激子,以使得使用磷光材料的OLED器件可以具有100%的内量子效率。
近来,已将铱络合物,例如双(2-苯基喹啉)(乙酰丙酮)铱(Ⅲ)(Ir(2-phq)2(acac))、双(2-苯并[b]噻吩-2-基吡啶)(乙酰丙酮)铱(Ⅲ)(Ir(btp)2(acac))和三(2-苯基喹啉)铱(Ⅲ)Ir(2-phq)3掺杂剂引入。
为了利用磷光材料获得高电流发光效率(Cd/A),需要优异的内部量子效率、高的色纯度和长寿命。特别是,参照图1,色纯度越高,即,CIE(X)越高,颜色灵敏度越差。结果,在高内量子效率下,非常难获得发光效率。因此,需要具有优异色纯度(CIE(X)≥0.65)和高发光效率的新型红色磷光化合物。
另一方面,除了上述的铱络合物之外,例如,4,4-N,N咔唑联苯(CBP)或其他金属络合物用作红色磷光化合物。然而,这些化合物在溶剂中不具有理想的溶解度,因而不能通过溶液工艺来形成发光层。发光层应当通过沉积工艺形成,因此,制造过程极为复杂,工艺效率也极低。另外,沉积工艺中的废料非常多,导致生产成本增大。
发明内容
本发明的目的是提供一种磷光化合物和使用该化合物的有机发光二极管器件以解决现有技术的不足之处。
本发明为解决其技术问题所采用的技术方案是:
一种磷光化合物,其特征在于:其结构式如式1和式2所示,
在上述化学式1和化学式2中Ar1和Ar2分别独立地选自C6~C60芳基,芴基,包括O,N,S,Si和P其中至少一种杂原子的C2~C60杂环基,C3~C60脂环族和C6~C60芳香族环的稠环基,C2~C20烯基,C2~C20炔基中的一种。L1分别独立地选自由单键、C6~C60亚芳基、芴烯基组成的基团,C3~C60脂环族和C6~C60芳香族环的稠环基,C2~C60杂环基中的一种。X1~X2独立地选自N原子或C原子,其中X1至X2中的至少一个为N。其中Y选自O,S和Se。其中Z选自O,S,Se和NAr3。
进一步的,所述的Ar3选自C6~C60芳基,芴基,包括O,N,S,Si和P其中至少一种杂原子的C2~C60杂环基,C3~C60脂环族和C6~C60芳香族环的稠环基,C2~C20烯基,C2~C20炔基中的一种。
进一步的,所述的结构式1和结构式2独立地选自以下任一式3至式10化合物:
进一步的,所述的磷光化合物独立地选自下列化合物:
进一步的,所述的有机电致发光器件顺次包括沉积的阳极,空穴注入层,空穴传输层,发光层,电子传输层,电子注入层和阴极,所述磷光化合物作为发光层的主体材料。
本发明的优点在于:本发明使用式1和式2所示的磷光化合物作为有机发光二极管器件的发光层,具有优异的色纯度和亮度以及延长的耐久性效果。
附图说明
图1为有机电发光二极管发光色度和可见度关系图。
图2为在本发明的实施方案中使用的化合物铜(Ⅱ)酞菁(CuPc),NPB,(mxmq)2Ir(acac),Alq3和CBP的结构式。
具体实施方式
为了使本发明实现的技术手段、创作特征、达成目的与功效易于明白了解,下面结合图示与具体实施例,进一步阐述本发明。
由于结构式如式1和式2的红色磷光化合物均具有优异的色纯度、高亮度和优异的发光效率,现以RH-001、RH-014、RH-022、RH-145、RH-158和RH-166制备方法和测试结果为例,证明本发明提供的技术方案和达到的技术效果。
以下实施方案中,NPB为4,4’-双[N-(1-萘基)-N-苯氨基]联苯,CBP为4,4’-N,N’-二咔哇联苯,CuPc为酞菁铜,LiF氟化锂,ITO为氧化铟锡,Alq3为三(8-羟基喹啉)铝。
LC-MS:液相色谱-质谱联用仪,M/Z:质子数/电荷数的比值。
形成例
1.中间体Sub-1的合成:
在2000mL反应瓶中加入1-羟基-8-溴萘(150.0g,672.4mmol),2-硝基苯基硼酸(123.5g,739.7mmol),四(三苯基膦)钯(5mol%),碳酸钾(278.8g,2017.3mmol),四氢呋喃(8000mL)和水(800mL)。反应体系升温至80℃,氮气保护下反应12小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到中间体Sub-1(114.2g,收率64%)LC-MS:M/Z 266.3(M+H)+。
2.中间体Sub-2的合成:
在1000mL反应瓶中加入中间体Sub-1(110.0g,414.7mmol)和亚磷酸三乙酯(700mL)。反应体系升温至80℃,氮气保护下反应18小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到中间体Sub-2(61.4g,收率63%)LC-MS:M/Z 234.3(M+H)+。
3.中间体Sub-3的合成:
在1000mL反应瓶中加入中间体Sub-2(60.0g,257.2mmol)和二氯甲烷(500mL),在0℃下滴加三氟甲磺酸酐(108.8g,385.8mmol)的二氯甲烷溶液(200mL)。搅拌过夜后,用饱和碳酸氢钠淬灭反应。分离有机相,用饱和食盐水洗涤并经硫酸钠干燥。蒸发掉溶剂后,粗产物用柱色谱纯化,用二氯甲烷作为洗脱剂得到中间体Sub-3(70.5g,收率75%)LC-MS:M/Z366.3(M+H)+。
4.中间体Sub-4的合成:
在2000mL反应瓶中加入中间体Sub-3(70.0g,191.6mmol),2-甲硫基苯硼酸(35.4g,210.8mmol),四(三苯基膦)钯(5mol%),碳酸钾(79.4g,574.8mmol),四氢呋喃(600mL)和水(600mL)。反应体系升温至80℃,氮气保护下反应12小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到中间体Sub-4(51.4g,收率79%)LC-MS:M/Z 340.5(M+H)+。
5.中间体Sub-5的合成:
在500mL反应瓶中加入中间体Sub-4(50.0g,147.3mmol),过氧化氢(32.6g,368.2mmol),乙酸(600mL)加入圆底烧瓶中并在室温下搅拌。反应完成后,除去乙酸,加入水析出固体,将固体溶解在二氯甲烷中,过柱分离浓缩,得到中间体Sub-5(42.9g,收率82%)LC-MS:M/Z 356.5(M+H)+。
6.中间体Sub-6的合成:
在500mL反应瓶中加入中间体Sub-5(40.0g,112.5mmol)溶于过量的硫酸(200mL)并在40℃下搅拌3天。当反应完成后,用0.2N-氢氧化钠水溶液将溶液中和至pH8-9。过滤后,将溶液用二氯甲烷萃取并浓缩,过柱分离并重结晶,得到中间体Sub-6(28.4g,收率78%)LC-MS:M/Z 324.4(M+H)+。
7.中间体Sub-7的合成:
在2000mL反应瓶中加入中间体Sub-6(28.0g,86.6mmol),硝基甲烷(150mL)溶于二氯甲烷(700mL),在氮气氛围下将温度降至0℃。加入三氯化铁(70.2g,432.9mmol)后搅拌1小时。加入甲醇(150mL)后,用水(200mL)萃取有机层。减压浓缩有机层,然后通过柱色谱分离,得到中间体Sub-7(19.2g,收率69%)LC-MS:M/Z 322.4(M+H)+。
8.RH-001的合成:
在250mL三口烧瓶中加入中间体I-1(3.0g,9.1mmol),中间体Sub-7(3.5g,10.9mmol),三(二亚苄基丙酮)二钯(4mol%),三叔丁基膦(8mol%),叔丁醇钾(3.1g,27.2mmol)和邻二甲苯(80mL)。反应体系升温至120℃,氮气保护下反应14小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到RH-001(4.2g,收率75%)。LC-MS:M/Z 616.7(M+H)+。
9.RH-014的合成:
在250mL三口烧瓶中加入中间体I-2(3.0g,6.2mmol),中间体Sub-7(2.4g,7.4mmol),三(二亚苄基丙酮)二钯(4mol%),三叔丁基膦(8mol%),叔丁醇钾(2.1g,18.6mmol)和邻二甲苯(80mL)。反应体系升温至120℃,氮气保护下反应14小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到RH-014(3.4g,收率72%)。LC-MS:M/Z 771.9(M+H)+。
10.RH-022的合成:
在250mL三口烧瓶中加入中间体I-3(3.0g,7.4mmol),中间体Sub-7(2.8g,8.8mmol),三(二亚苄基丙酮)二钯(4mol%),三叔丁基膦(8mol%),叔丁醇钾(2.5g,22.1mmol)和邻二甲苯(80mL)。反应体系升温至120℃,氮气保护下反应14小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到RH-022(3.6g,收率71%)。LC-MS:M/Z 692.8(M+H)+。
11.RH-145的合成:
在250mL三口烧瓶中加入中间体I-4(3.0g,9.1mmol),中间体Sub-7(3.5g,10.9mmol),三(二亚苄基丙酮)二钯(4mol%),三叔丁基膦(8mol%),叔丁醇钾(3.1g,27.2mmol)和邻二甲苯(80mL)。反应体系升温至120℃,氮气保护下反应14小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到RH-145(4.0g,收率72%)。LC-MS:M/Z 616.7(M+H)+。
12.RH-158的合成:
在250mL三口烧瓶中加入中间体I-5(3.0g,6.2mmol),中间体Sub-7(2.4g,7.4mmol),三(二亚苄基丙酮)二钯(4mol%),三叔丁基膦(8mol%),叔丁醇钾(2.1g,18.6mmol)和邻二甲苯(80mL)。反应体系升温至120℃,氮气保护下反应14小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到RH-158(3.5g,收率74%)。LC-MS:M/Z 771.9(M+H)+。
13.RH-166的合成:
在250mL三口烧瓶中加入中间体I-6(3.0g,7.4mmol),中间体Sub-7(2.8g,8.8mmol),三(二亚苄基丙酮)二钯(4mol%),三叔丁基膦(8mol%),叔丁醇钾(2.5g,22.1mmol)和邻二甲苯(80mL)。反应体系升温至120℃,氮气保护下反应14小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥,浓缩,重结晶所得粗品过硅胶柱得到RH-166(3.7g,收率72%)。LC-MS:M/Z 692.8(M+H)+。
实施方案
1.第一实施方案
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
在0.9mA下,亮度等于1832cd/m2(5.4V)。此时,CIEx=0.658,y=0.340。
2.第二实施方案
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
在0.9mA下,亮度等于1800cd/m2(5.3V)。此时,CIEx=0.657y=0.340。
3.第三实施方案
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
在0.9mA下,亮度等于1819cd/m2(5.5V)。此时,CIEx=0.657,y=0.341。
4.第四实施方案
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
在0.9mA下,亮度等于1831cd/m2(5.4V)。此时,CIEx=0.658,y=0.340。
5.第五实施方案
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
在0.9mA下,亮度等于1793cd/m2(5.4V)。此时,CIEx=0.657,y=0.341。
6.第六实施方案
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
在0.9mA下,亮度等于1808cd/m2(5.6V)。此时,CIEx=0.657,y=0.340。
7.对比例
使ITO玻璃基板图案化,以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。
在0.9mA下,亮度等于1409cd/m2(5.7V)。此时,CIEx=0.657,y=0.341。如图1所示显示有机电致发光器件的色纯度增加(即随色度坐标的X值变得更大)可见度降低。
依据上述实施方案和对比例,效率,色度坐标和亮度的特性显示在下表1中。
表1
如表1所示,甚至当色纯度高时,该器件在低电压下也高效率地运行。并且,与对比例相比,第二实施方案电流效率增加30%以上。
以上显示和描述了本发明的基本原理、主要特征和本发明的优点。本行业的技术人员应该了解,本发明不受上述实施例的限制,上述实施例和说明书中描述的只是说明本发明的原理,在不脱离本发明精神和范围的前提下本发明还会有各种变化和改进,这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等同物界定。
Claims (5)
2.如权利要求1所述磷光化合物,其特征在于:其中Ar3选自C6~C60芳基,芴基,包括O、N、S、Si和P其中至少一种杂原子的C2~C60杂环基,C3~C60脂环族和C6~C60芳香族环的稠环基,C2~C20烯基,C2~C20炔基中的一种。
5.一种使用权利要求1-4中任意一项所述的磷光化合物的有机电致发光二极管器件,其特征在于:所述的有机电致发光器件顺次包括沉积的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极,所述磷光化合物作为发光层的主体材料。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910807578.0A CN110903305A (zh) | 2019-08-29 | 2019-08-29 | 一种磷光化合物和使用该化合物的有机发光二极管器件 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910807578.0A CN110903305A (zh) | 2019-08-29 | 2019-08-29 | 一种磷光化合物和使用该化合物的有机发光二极管器件 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN110903305A true CN110903305A (zh) | 2020-03-24 |
Family
ID=69814553
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910807578.0A Pending CN110903305A (zh) | 2019-08-29 | 2019-08-29 | 一种磷光化合物和使用该化合物的有机发光二极管器件 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110903305A (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111039850A (zh) * | 2019-09-04 | 2020-04-21 | 宁波卢米蓝新材料有限公司 | 一种稠环化合物及其制备方法和应用 |
WO2022059923A1 (ko) * | 2020-09-18 | 2022-03-24 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
CN114478562A (zh) * | 2020-10-23 | 2022-05-13 | 上海和辉光电股份有限公司 | 一种化合物及其应用 |
CN114630831A (zh) * | 2019-10-25 | 2022-06-14 | 默克专利有限公司 | 可用于有机电子器件中的化合物 |
CN115504983A (zh) * | 2022-02-28 | 2022-12-23 | 陕西莱特迈思光电材料有限公司 | 含氮化合物及包含其的电子元件和电子装置 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150077220A (ko) * | 2013-12-27 | 2015-07-07 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20150121337A (ko) * | 2014-04-18 | 2015-10-29 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN108391433A (zh) * | 2015-12-04 | 2018-08-10 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
WO2018159964A1 (en) * | 2017-02-28 | 2018-09-07 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
CN108727398A (zh) * | 2018-06-28 | 2018-11-02 | 宁波卢米蓝新材料有限公司 | 一种稠环化合物及其制备方法和用途 |
CN109451739A (zh) * | 2016-07-27 | 2019-03-08 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包括所述有机电致发光化合物的有机电致发光装置 |
WO2019107822A1 (en) * | 2017-11-28 | 2019-06-06 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
WO2019143184A1 (en) * | 2018-01-19 | 2019-07-25 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
-
2019
- 2019-08-29 CN CN201910807578.0A patent/CN110903305A/zh active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150077220A (ko) * | 2013-12-27 | 2015-07-07 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20150121337A (ko) * | 2014-04-18 | 2015-10-29 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN108391433A (zh) * | 2015-12-04 | 2018-08-10 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
CN109451739A (zh) * | 2016-07-27 | 2019-03-08 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包括所述有机电致发光化合物的有机电致发光装置 |
WO2018159964A1 (en) * | 2017-02-28 | 2018-09-07 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
WO2019107822A1 (en) * | 2017-11-28 | 2019-06-06 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
WO2019143184A1 (en) * | 2018-01-19 | 2019-07-25 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
CN108727398A (zh) * | 2018-06-28 | 2018-11-02 | 宁波卢米蓝新材料有限公司 | 一种稠环化合物及其制备方法和用途 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111039850A (zh) * | 2019-09-04 | 2020-04-21 | 宁波卢米蓝新材料有限公司 | 一种稠环化合物及其制备方法和应用 |
CN111039850B (zh) * | 2019-09-04 | 2022-02-25 | 宁波卢米蓝新材料有限公司 | 一种稠环化合物及其制备方法和应用 |
CN114630831A (zh) * | 2019-10-25 | 2022-06-14 | 默克专利有限公司 | 可用于有机电子器件中的化合物 |
WO2022059923A1 (ko) * | 2020-09-18 | 2022-03-24 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
CN114478562A (zh) * | 2020-10-23 | 2022-05-13 | 上海和辉光电股份有限公司 | 一种化合物及其应用 |
CN115504983A (zh) * | 2022-02-28 | 2022-12-23 | 陕西莱特迈思光电材料有限公司 | 含氮化合物及包含其的电子元件和电子装置 |
CN115504983B (zh) * | 2022-02-28 | 2023-11-14 | 陕西莱特迈思光电材料有限公司 | 含氮化合物及包含其的电子元件和电子装置 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109593097B (zh) | 一种磷光主体化合物及其使用该化合物的有机电致发光器件 | |
CN110467630A (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
CN109678867B (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
CN110903305A (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
US7449593B2 (en) | Silicon-contained anthracene compound for organic electroluminescent device | |
CN109678875B (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
CN110330481B (zh) | 一种红色磷光化合物和使用该化合物的有机发光器件 | |
CN110903301A (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
CN110746401A (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
KR20100118700A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
CN111153888A (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
KR20110116635A (ko) | 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
KR20120038056A (ko) | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
KR20120020901A (ko) | 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
CN110437242A (zh) | 一种红色磷光化合物和使用该化合物的有机电致发光器件 | |
KR20120033017A (ko) | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
CN111978355A (zh) | 有机化合物和使用该化合物的有机电致发光器件 | |
CN110903300A (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
CN110437241A (zh) | 一种红色磷光主体化合物和使用该化合物的有机发光器件 | |
CN110981913A (zh) | 绿色磷光化合物和使用该化合物的有机电致发光器件 | |
KR20120020818A (ko) | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
CN112079876A (zh) | 一种有机化合物和使用该化合物的有机电致发光器件 | |
CN110872301A (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
CN107056807A (zh) | 一种以均苯为核心的化合物及其在有机电致发光器件中的应用 | |
CN106467551B (zh) | 一种以均苯为核心的光电材料及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200324 |
|
RJ01 | Rejection of invention patent application after publication |