CN113896735B - 一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有机电致发光器件中的应用 - Google Patents

一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有机电致发光器件中的应用 Download PDF

Info

Publication number
CN113896735B
CN113896735B CN202111352483.8A CN202111352483A CN113896735B CN 113896735 B CN113896735 B CN 113896735B CN 202111352483 A CN202111352483 A CN 202111352483A CN 113896735 B CN113896735 B CN 113896735B
Authority
CN
China
Prior art keywords
red light
coumarin
pyrazine
light material
organic electroluminescent
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.)
Active
Application number
CN202111352483.8A
Other languages
English (en)
Other versions
CN113896735A (zh
Inventor
蔡昕良
李成龙
王悦
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jilin University
Original Assignee
Jilin University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jilin University filed Critical Jilin University
Priority to CN202111352483.8A priority Critical patent/CN113896735B/zh
Publication of CN113896735A publication Critical patent/CN113896735A/zh
Application granted granted Critical
Publication of CN113896735B publication Critical patent/CN113896735B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • 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
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

一种基于香豆素并吡嗪结构的化合物作为热活化延迟红光材料在有机电致发光器件中的应用，属于有机电子材料技术领域。本发明以香豆素并吡嗪为母核旨在获得一种新的高效红光TADF材料，解决现有红光TADF材料稀缺及发光效率低的问题。本发明所述的基于香豆素并吡嗪结构的热活化延迟红光材料可以用于制备有机电致发光器件，特别是作为客体材料掺杂到主体材料中作为发光层使用。本发明提供的基于香豆素并吡嗪结构的热活化延迟红光材料通过简单而有效地将发射光波长在短波区域的优良发光染料香豆素与吡嗪整合在一起，一方面获得吸电子能力强的片段，结合给电子基团，满足红光材料强电荷转移的设计要求；另一方面增强分子刚性，确保高荧光量子效率，获得了高效长波长发光的有机电致发光器件。

Description

一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有 机电致发光器件中的应用
技术领域
本发明属于有机电子材料技术领域，具体涉及一种基于香豆素并吡嗪结构的化合物作为热活化延迟红光材料在有机电致发光器件中的应用。
背景技术
近年来，由于在生物成像、光纤通讯、有机发光二极管(OLEDs)以及有机固态激光器等领域的潜在应用前景，红光特别是近红外光有机发光材料已经引起了科研工作者的广泛关注。目前，基于铱、锇或铂等贵金属的红光磷光材料已经获得了较高的效率，但贵金属的稀有性和高成本限制了其在工业生产中的大规模应用。作为一种廉价的材料替代体系，不含贵金属的热活化延迟荧光(Thermally Activated Delayed Fluorescence,TADF)材料由于可以通过三重态到单重态的反向系间窜越(RISC)过程实现100％的内量子效率，已经逐渐成为有机电致发光 (Organic Light Emitting Diodes,OLEDs)领域研究的新热点。目前，高效的蓝光、绿光TADF材料已经取得了突破性的进展，外量子效率接近甚至达到了磷光器件的水平。然而，高性能的红光TADF材料发展却较为缓慢。因此，开发高效红光TADF材料具有重要的科研和应用价值。
近来研究表明，香豆素和吡嗪类发光材料具有较好的光物理和光化学性质，但由于其较弱的吸电子能力，其发射波长通常处于蓝光和绿光区域，限制了其在发光领域的应用范围。通过将香豆素和吡嗪类衍生物结合不仅可以有效增加吸电子能力，而且可以增加分子刚性降低非辐射跃迁，再结合给电子基团，从而可以获得获得高效红光TADF材料。
发明内容
鉴于上述现有技术不足，本发明的目的在于提供了一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有机电致发光器件中的应用，本发明以香豆素并吡嗪为母核旨在获得一种新的高效红光TADF材料，解决现有红光TADF材料稀缺及发光效率低的问题。
本发明所述的一种基于香豆素并吡嗪结构的热活化延迟红光材料，其特征在于：其结构如通式(Ⅰ)所示：
其中，A代表受体基团；D代表给体基团；
L为连接基团，选自氢、单键、取代或未取代的C6-C30的亚芳基；
虚线表示键连或者不键连；
所述受体基团选自芳基硼类取代基、含氮杂环类取代基、含氰基类取代基、含羰基类取代基、含氟类取代基、砜类取代基和含磷氧基类取代基；
所述给体基团选自取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的 C12-C40的二苯胺基及其衍生物基团、取代或未取代的C18-C60的三苯胺基及其衍生物基团、取代或未取代的C13-C40的吖啶基及其衍生物基团、取代或未取代的C12-C40的吩噻嗪及其衍生物基团、取代或未取代的C12-C40的吩噁嗪及其衍生物基团、取代或未取代的C12-C40的二苯并氮杂硅烷及其衍生物基团。
优选的，A选自氰基、氰基苯基、含氮杂环类取代基；D选自取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、取代或未取代的C13-C40的吖啶基及其衍生物基团、取代或未取代的C12-C40的吩噻嗪及其衍生物基团、取代或未取代的C12-C40的吩噁嗪及其衍生物基团、取代或未取代的C12-C40的二苯并氮杂硅烷及其衍生物基团；L选自氢、单键、亚苯基、亚萘基、亚蒽基、亚非那烯、亚三亚苯基。
进一步优选的，A选自氰基；L选自亚苯基；D选自如下结构之一：
波浪线表示与L键连。
本发明所述具体实施方案中，基于香豆素并吡嗪结构的热活化延迟红光材料作为发光层客体的结构式如下之一所示，但不限于此：
本发明所述具体实施方案中，基于香豆素并吡嗪结构的热活化延迟红光材料的制备步骤和条件可参考本领域类似反应的步骤和条件。
本发明提供了如通式Ⅰ所示，基于香豆素并吡嗪结构的热活化延迟红光材料的制备方法：
反应步骤中涉及的中间反应物结构为：
本发明提供的基于香豆素并吡嗪结构的热活化延迟红光材料通过简单而有效地将发射光波长在短波区域的优良发光染料香豆素与吡嗪整合在一起，一方面获得吸电子能力强的片段，结合给电子基团，满足红光材料强电荷转移的设计要求；另一方面增强分子刚性，确保高荧光量子效率，获得了高效长波长发光的有机电致发光器件。
本发明所述的基于香豆素并吡嗪结构的热活化延迟红光材料可以用于制备有机电致发光器件，该有机电致发光器件由阳极、阴极和布置在阳极和阴极之间的至少一层有机功能层组成；且有机功能层中应当包括发光层，本发明所述的基于香豆素并吡嗪结构的热活化延迟红光化合物作为客体材料掺杂到主体材料中作为发光层使用。
具体实施方式
下面结合具体的实施例，对本发明作进一步地详细说明，但本发明的实施方式不限于此。下列实施例中未注明具体条件的实验方法，按照常规方法和条件，或按照商品说明书选择。基于本发明中的实施例，本领域技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明的保护范围。
合成实施例1
表1.合成实施例产物数据汇总：
以化合物7、37为例说明合成实施例实验具体细节：
将6.21g 2,3-二氨基苯酚(50mmol)和10.51g苯偶酰(50mmol)按照1：1的摩尔比例加入到300mL醋酸和醋酸钠(醋酸和醋酸钠的摩尔比为1：1)溶液中，回流6个小时，冷却至室温后，将反应液倒入水中，过滤，分别用水和甲醇洗涤滤饼，所得滤饼真空干燥，得到2,3-二苯喹喔啉-5-酚。
将5.97g 2,3-二苯喹喔啉-5-酚(20mmol)、3.70g 4-溴苯甲醛(22mmol)、1.32g丙二腈 (22mmol)加入300mL乙醇中，加10滴三乙胺，在氮气氛围下，加热回流8小时。待反应完成后，停止加热，反应体系自行冷却至室温析出固体，过滤并用乙醇洗滤饼，烘箱干燥后得到固体。将所得固体与碘等摩尔比加入200mL乙醇溶液中，加热回流反应12h。待反应完成后，停止加热，反应体系自行冷却至室温析出固体，过滤并用乙醇洗滤饼，烘箱干燥后得到7-(4-溴苯)-9-芴酮-2,3-二苯-9H-吡喃酮并[2,3-f]喹喔啉-8-腈。
将2.65g 7-(4-溴苯)-9-芴酮-2,3-二苯-9H-吡喃酮并[2,3-f]喹喔啉-8-腈(5mmol)和中间反应物1.23g 4-苯胺基联苯(5.5mmol)按照1：1.1经一步反应或者两步同类型反应在氮气的保护下，在30mL邻二氯苯中与5.38g碳酸铯、0.075g双(二亚苄基丙酮)钯和0.025g三叔丁基膦加热回流24小时后，之后冷却至室温，将反应液过滤，向滤液中加入水，用二氯甲烷萃取有机相，分离出有机相后浓缩，用二氯甲烷洗脱剂进行柱层析分离得到目标产物，然后通过真空升华得到3.02g黄色纯品产物(产率87％)，即化合物7。
将6.21g 2,3-二氨基苯酚(50mmol)和10.41g菲-9,10-二酮(50mmol)按照1:1的比例加入到300mL醋酸和醋酸钠(醋酸和醋酸钠的摩尔比为1：1)溶液中，回流6个小时，冷却至室温后，将反应液倒入水中，过滤，分别用水和甲醇洗涤滤饼，所得滤饼真空干燥，得到二苯并[a,c]吩嗪-10-酚。
将5.93g二苯并[a,c]吩嗪-10-酚(20mmol)、3.70g 4-溴苯甲醛(20mmol)、1.32g丙二腈 (22mmol)加入300mL乙醇中，加10滴三乙胺，在氮气氛围下，加热回流8小时。待反应完成后，停止加热，反应体系自行冷却至室温析出固体，过滤并用乙醇洗滤饼，烘箱干燥后得到固体。将所得固体与碘等摩尔比加入200mL乙醇溶液中，加热回流反应12h。待反应完成后，停止加热，反应体系自行冷却至室温析出固体，过滤并用乙醇洗滤饼，烘箱干燥后得到或 4-(4-溴苯)-2-芴酮-2H-二苯并[a,c]吡喃酮并[2,3-h]吩嗪-3-腈。
将2.64g 4-(4-溴苯)-2-芴酮-2H-二苯并[a,c]吡喃酮并[2,3-h]吩嗪-3-腈(5mmol)和中间反应物1.82g 10H-螺[吖啶-9,9,-芴](5.5mmol)按照1：1.1经一步反应或者两步同类型反应在氮气的保护下，在30mL邻二氯苯中与5.38g碳酸铯、0.075g双(二亚苄基丙酮)钯和0.025g三叔丁基膦加热回流24小时后，之后冷却至室温，将反应液过滤，向滤液中加入水，用二氯甲烷萃取有机相，分离出有机相后浓缩，用二氯甲烷洗脱剂进行柱层析分离得到目标产物，然后通过真空升华得到3.15g黄色纯品产物(产率81％)，即化合物37。
获得的目标化合物有关数据见表1。
效果实施例
以下利用本发明的材料制备电致发光器件实施例，具体的器件制备工艺及器件性能测试实验操作如下：透明ITO玻璃作为制备器件的基底材料，后先以5vt％ITO洗液超声处理30min，之后依次以蒸馏水(2次)、丙酮(2次)、异丙醇(2次)超声洗涤，最后将ITO玻璃保存在异丙醇中。每次使用前，先用丙酮棉球和异丙醇棉球小心擦拭ITO玻璃表面，待异丙醇冲洗后烘干，之后用等离子体处理5min。器件的制备利用真空镀膜设备采用真空蒸镀工艺完成，当真空蒸镀系统的真空度达到5*10-4Pa以下时开始蒸镀，沉积速率由赛恩斯膜厚仪，利用真空蒸镀工艺在ITO玻璃上依次沉积各种有机层(HIL、HTL、EML(Host:Dopant)、ETL，HIL、HTL、EML(Host:Dopant)、ETL分别表示空穴注入层、空穴传输层、发光层(主体：客体)和电子传输层)及LiF电子注入层和金属Al电极(具体器件结构见如下效果实施例)。器件的电流、电压、亮度、发光光谱等特性采用PR655光谱扫描亮度计和Keithley K 2400数字源表系统同步测试。器件的性能测试在空气中进行。
实施例1
实施例1有机电致发光器件结构为[ITO/TAPC(45nm)/TCTA(10nm)/EML(DCzDPy:Dopant (5wt％),20nm)/B3PymPm(50nm)/LiF(1nm)/Al(100nm)]，EML代表发光层。应用实施例中发光层客体(Dopant)换成化合物1、5、7、9、14、17、18、21、25、27、29、34、37、38，掺杂比均为5wt％。效果实施例结果见表2。
表2.效果实施例1所提供的电致发光器件数据参数：
器件代号 发光层客体 启亮电压(V) 发光亮度(cd/m2) EQE(％)
应用实施例1 化合物1 2.4 100/1000 28.8/22.8
应用实施例2 化合物5 2.5 100/1000 30.2/21.9
应用实施例3 化合物7 2.4 100/1000 29.6/22.4
应用实施例4 化合物9 2.6 100/1000 29.3/21.8
应用实施例5 化合物14 2.4 100/1000 31.2/23.9
应用实施例6 化合物17 2.4 100/1000 30.6/23.4
应用实施例7 化合物18 2.5 100/1000 31.5/24.8
应用实施例8 化合物21 2.3 100/1000 29.2/23.9
应用实施例9 化合物25 2.6 100/1000 28.6/23.4
应用实施例10 化合物27 2.4 100/1000 30.5/26.2
应用实施例11 化合物29 2.5 100/1000 32.4/28.3
应用实施例12 化合物34 2.3 100/1000 30.9/24.4
应用实施例13 化合物37 2.4 100/1000 29.8/23.9
应用实施例14 化合物38 2.6 100/1000 32.2/25.9
依据效果实施例的结果证明，本发明所提供的基于香豆素并吡嗪结构的热活化延迟红光材料作为TADF红光客体材料应用于有机电致发光器件，实现外量子效率均超过25％，达到了 30％左右，是性能优良的红光客体材料。
应当理解的是，本发明的应用不限于上述的举例，对本领域普通技术人员来说，可以根据上述说明加以改进或变换，所有这些改进和变换都应属于本发明所附权利要求的保护范围。

Claims (4)

1.一种基于香豆素并吡嗪结构的热活化延迟红光材料，其特征在于：其结构如通式(Ⅰ)所示：
其中A代表受体基团，D代表给体基团；A选自氰基，L选自亚苯基，D选自如下结构之一，
波浪线表示与L键连。
2.如权利要求1所述的一种基于香豆素并吡嗪结构的热活化延迟红光材料，其特征在于：其结构式如下之一所示，
3.权利要求1或2所述的一种基于香豆素并吡嗪结构的热活化延迟红光化合物在有机电致发光器件中的应用。
4.如权利要求3所述的基于香豆素并吡嗪结构的热活化延迟红光化合物在有机电致发光器件中的应用，其特征在于：基于香豆素并吡嗪结构的热活化延迟红光化合物作为客体材料掺杂到主体材料中作为发光层使用。
CN202111352483.8A 2021-11-16 2021-11-16 一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有机电致发光器件中的应用 Active CN113896735B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111352483.8A CN113896735B (zh) 2021-11-16 2021-11-16 一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有机电致发光器件中的应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111352483.8A CN113896735B (zh) 2021-11-16 2021-11-16 一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有机电致发光器件中的应用

Publications (2)

Publication Number Publication Date
CN113896735A CN113896735A (zh) 2022-01-07
CN113896735B true CN113896735B (zh) 2023-10-27

Family

ID=79194383

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111352483.8A Active CN113896735B (zh) 2021-11-16 2021-11-16 一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有机电致发光器件中的应用

Country Status (1)

Country Link
CN (1) CN113896735B (zh)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106206958A (zh) * 2015-04-30 2016-12-07 北京维信诺科技有限公司 一种白光有机电致发光器件
CN108658960A (zh) * 2018-06-01 2018-10-16 中节能万润股份有限公司 一种热活化延迟荧光材料及其应用

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106206958A (zh) * 2015-04-30 2016-12-07 北京维信诺科技有限公司 一种白光有机电致发光器件
CN108658960A (zh) * 2018-06-01 2018-10-16 中节能万润股份有限公司 一种热活化延迟荧光材料及其应用

Also Published As

Publication number Publication date
CN113896735A (zh) 2022-01-07

Similar Documents

Publication Publication Date Title
KR101465270B1 (ko) 유기 전계발광 소자용 물질
JP5951544B2 (ja) 有機エレクトロルミネセンス素子のための新規材料
KR100974562B1 (ko) 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자
CN109678844B (zh) 一种橙红光热激活延迟荧光材料及有机电致发光器件
CN112321587B (zh) 一种有机化合物、电致发光材料及其应用
CN110016058B (zh) 金属配合物、有机电致发光材料、有机电致发光器件
JP5641688B2 (ja) 電気発光用の有機金属化合物及びこれを使用する有機電気発光素子
Kotchapradist et al. N-coumarin derivatives as hole-transporting emitters for high efficiency solution-processed pure green electroluminescent devices
KR20220065850A (ko) 금속 착물 및 그 응용
CN108203403A (zh) 具有热致延迟荧光的发光材料、其应用及电致发光器件
CN111479799A (zh) 有机化合物及包含其的有机电致发光元件
CN110256439B (zh) 有机电致发光材料及器件
CN112939993B (zh) 一种苯并吡喃类发光辅助材料及其制备方法和有机电致发光器件
CN113354689A (zh) 一种含联苯衍生物配位的中性铱配合物及其制备方法和应用
CN111170928B (zh) 化合物、显示面板以及显示装置
CN114044781B (zh) 一种以香豆素并菲啰啉吡嗪为母核的热活化延迟红光材料及其在有机电致发光器件中的应用
CN117736218A (zh) 一种螺环羰基氮化合物、聚合物、混合物及其应用
CN113896735B (zh) 一种基于香豆素并吡嗪结构的热活化延迟红光材料及其在有机电致发光器件中的应用
CN111285877A (zh) 有机电致发光材料及器件
CN111574535B (zh) 一种有机电致发光化合物及其制备方法和应用
CN113121500B (zh) 一种作为oled掺杂材料的磷光铂配合物及其应用
CN113292606B (zh) 金属配合物、有机电致发光材料、发光器件和电子设备
CN114685465B (zh) 一种含酮的有机化合物及包含该有机化合物的有机电致发光器件
CN113121508B (zh) 一种含金属铂的有机电致发光材料及其应用
CN116082318B (zh) 一种蓝光发光辅助材料及其制备方法和有机电致发光器件

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
GR01 Patent grant
GR01 Patent grant