CN113620996A - 一种有机金属配合物和及其有机光电元件 - Google Patents

一种有机金属配合物和及其有机光电元件 Download PDF

Info

Publication number
CN113620996A
CN113620996A CN202110781965.9A CN202110781965A CN113620996A CN 113620996 A CN113620996 A CN 113620996A CN 202110781965 A CN202110781965 A CN 202110781965A CN 113620996 A CN113620996 A CN 113620996A
Authority
CN
China
Prior art keywords
organic
unsubstituted
organometallic complex
substituted
layer
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
Application number
CN202110781965.9A
Other languages
English (en)
Inventor
王子兴
申屠晓波
吴空物
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.)
Zhejiang Huadisplay Optoelectronics Co Ltd
Original Assignee
Zhejiang Huadisplay Optoelectronics Co Ltd
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 Zhejiang Huadisplay Optoelectronics Co Ltd filed Critical Zhejiang Huadisplay Optoelectronics Co Ltd
Priority to CN202110781965.9A priority Critical patent/CN113620996A/zh
Publication of CN113620996A publication Critical patent/CN113620996A/zh
Priority to CN202210170033.5A priority patent/CN114315914B/zh
Pending legal-status Critical Current

Links

Images

Classifications

    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/006—Palladium compounds
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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]
    • H10K50/17—Carrier injection layers
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • 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
    • 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
    • C09K2211/1018—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
    • C09K2211/1044—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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

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

Abstract

本发明提供了有机金属配合物及包含其的有机光电元件，特别是有机电致发光二极管，其中有机金属配合物的结构如式(I)所示：
Figure DDA0003155945560000011
M选自铂(Pt)或钯(Pd)；有机金属配合物和有机光电元件的详细信息可以通过本文提供的具体描述进行理解。本发明提供的有机金属化合物可以获得高效率、长寿命的OLED器件。铂和钯金属在地壳中含量丰富，有替代稀有金属铱形成可持续使用的有机金属配合物，具有很好的商业应用前景。

Description

一种有机金属配合物和及其有机光电元件
技术领域
本发明属于有机光电领域，具体涉及一种铂金属配合物及包含其的光电元件，特别是有机电致发光二极管。
背景技术
有机电致发光二极管(OLED)作为一种新型的显示技术，具有自发光、宽视角、低能耗、效率高、薄、色彩丰富、响应速度快，适用温度范围广、低驱动电压、可制作柔性可弯曲与透明的显示面板以及环境友好等独特优点，可以应用在平板显示器和新一代照明上，也可以作为LCD的背光源。
20世纪80年代底发明以来，有机电致发光器件已经在产业上有所应用，OLED 发光分为荧光发光和磷光发光两种方式，根据理论推测，由载流子复合产生的单重激发态与三重激发态的比例为1∶3，所以使用小分子荧光材料时，能用于发光的仅为全部能量的25％，其余的75％的能量因三重激发态的非发光机制而损失掉，故一般认为荧光材料的内部量子效率极限为25％。1998年Forrest教授等人发现三线态磷光可以在室温下利用，并将原来内量子效率的上限提升到100％，三重态磷光体常常都是重金属原子组成的络合物，利用重原子效应，强烈的自旋轨域耦合作用使得原本被禁止的三重态能量以磷光的形式发光，量子效率也随之大幅提升。
目前有机OLED组件中的发光层几乎全部使用主客体发光体系机制，即在主体材料中掺杂客体发光材料，一般来说，有机主体材料的能系要比客体材料大，即能量由主体传递给客体，使客体材料被激发而发光。常用的磷光有机主体材料具有高三线态能级，当有机主体材料被电场激发时，三线态能量能够有效地从有机主体材料转移到客体磷光材料。常用的有机客体材料为铱和铂金属化合物。目前铱金属化合物应用于商业OLED材料已经成为主流，但是铂，钯配合物材料和器件的开发仍然存在一些技术难点，比如OLED要求效率高，寿命长，操作电压更低。
本发明发现拓展铂，钯金属化合物配体的设计，引入刚性的四齿配体单元、取代基等可以改善铂，钯金属化合物的发光效率，在提升铂金属化合物热稳定性，将此类铂，钯金属化合物应用于有机光电器件，特别是在有机电致发光器件中，可以提升电流效率、降低元器件的操作电压，获得长寿命的有机光电元件。
发明内容
本发明的目的是提供一种铂，钯金属配合物及包含其的光电元件，特别是有机电致发光二极管。
本发明提供的一种铂，钯金属配合物，其特征在于：铂，钯金属配合物的结构如式(I)示：
Figure BDA0003155945540000021
其中，在式(I)中，M选自铂(Pt)或钯(Pd)；X1至X3不存在、或独立地选自C-C、C＝C、C-O、C＝N、B-O、B-N、C-N、C-Si、O-Si化学键、O、S、N-R7、 B-R7、P-R7、O＝P-R7、C-R7R8、C＝O、S＝O、S(＝O)2或Si-R7R8的一种；Y1 至Y14独立地选自C或N或O；L1独立地选自O、N-R7、S中的一种；环CY1 至环CY5各自独立地与相应的Y1至Y14组成C6～C60的环基团和C1～C50杂环基团，CY1为五元环；R1至R8各自独立地选自氢、氘、CN、卤素、羟基、肼基、脒基、酰胺基、取代或未取代的C1～C60的烷基、取代或未取代的C2～C60的烯基、取代或未取代的C1～C60的烷氧基、取代或未取代的C1～C60的环烷基、取代或未取代的C1～C60的杂烷基、取代或未取代的C6～C60的芳基、取代或未取代的C1～C60的杂芳基、取代或未取代的C1～C60的胺基、取代或未取代的 C1～C60的硅基、取代或未取代的C6～C60的芳族稠环、取代或未取代的C1～C60 的杂芳族稠环；R1至R8各自独立地可被部分或全部氘代、各自独立地可被部分或全氟代；R1至R8可以根据价健原则不取代或多取代。
本发明的有机金属配合物，其特征在于，与金属M相连的原子与金属M形成共价键或配位健。
优选地，本发明所述的有机金属配合物，其特征在于式(I)中的
Figure BDA0003155945540000031
部分独立选自以下代表基团的一种：
Figure BDA0003155945540000032
其中，X8独立地选自O、S、N-R7、B-R7、P-R7、O＝P-R7、C-R7R8、C＝O、 S＝O、S(＝O)2或Si-R7R8的一种；Y为N或C-R9R10，R7、R8、R9、Ri0与权利要求1中R1所述相同。相邻的R1至R10可以成环。
优选地，本发明所述的有机金属配合物，其特征在于式(I)中的
Figure BDA0003155945540000033
Figure BDA0003155945540000034
部分独立地选自以下代表基团的一种：
Figure BDA0003155945540000041
其中，X8独立地选自O、S、N-R7、B-R7、P-R7、O＝P-R7、C-R7R8、C＝O、 S＝O、S(＝O)2或Si-R7R8的一种；Y为N或C-R9R10，R7、R8、R9、R10与权利要求1中R1所述相同。相邻的R1至Ri0可以成环。
优选地，本发明所述的有机金属配合物，其特征在于式(I)中的
Figure BDA0003155945540000042
部分独立地选自以下代表基团的一种：
Figure BDA0003155945540000043
其中，R1、R2、Y1、Y2、Y5权利要求1所述相同，X8独立地选自O、S、N-R6、 B-R6、P-R6、O＝P-R7、C-R7R8、C＝O、S＝O、S(＝O)2或Si-R7R8的一种；Y为 N或C-R9，R7、R8、R9与权利要求1中R1所述相同，当R9为2个或多个时，彼此相同或不同，相邻的R1至R9可以成环。
优选地，本发明所述的有机金属配合物，其特征在于，所述有机金属配合物式(I)选自以下代表结构的一种：
本发明涉及一种铂，钯金属配合物包含式(I)所述化合物与一种或多种与溶剂形成的制剂，所用的溶剂没有特别限制，可以使用本领域技术人员熟知的例如甲苯、二甲苯、均三甲苯、四氢化萘、十氢萘、双环己烷、正丁基苯、仲丁基苯、叔丁基苯等溶剂、四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、溴戊烷、氯己烷、溴己烷、氯环己烷、溴环己烷等卤化烃溶剂，氯苯、二氯苯、三氯苯等卤化不饱和烃溶剂，四氢呋喃、四氢吡喃等醚溶剂，苯甲酸烷基酯等酯类溶剂。
本发明还涉及一种有机光电器件，包括：第一电极；
第二电极，与所述第一电极相面对；
有机功能层，夹设于所述第一电极和所述第二电极之间；
其中，有机功能层包含所述的铂，钯金属配合物。
本发明还涉及一种有机电致发光器件，包括阴极层、阳极层和有机层，该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中至少一层，其中该器件的发光层中含有所述的铂，钯金属配合物。
本发明所述的有机电致发光器件发光层中含有所述铂，钯金属配合物和相应的主体材料，其中所述铂，钯金属配合物的质量百分数在0.1％-100％。
本发明所述的有机电致器件是有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)及有机内存器件(Organic Memory Element)、照明和显示装置中任意一种。
在本发明中，有机光电器件是可以利用喷溅涂覆法、电子束蒸发、真空蒸镀等方法在基板上蒸镀金属或具有导电性的氧化物以及它们的合金形成阳极；在制备得到的阳极表面按顺序蒸镀空穴注入层、空穴传输层、发光层、空穴阻挡层和电子传输层，以后再蒸镀阴极的方法制备。以上方法以外基板上按阴极、有机物层、阳极顺序蒸镀制作有机电致器件。所述有机物层是也可以包括空穴注入层、空穴传输层、发光层、空穴阻挡层及电子传输层等多层结构。在本发明中有机物层是采用高分子材料按溶剂工程(旋转涂膜、薄带成型、刮片法、丝网印刷、喷墨印刷或热成像等)替代蒸镀方法制备，可以减少器件层数。
根据本发明的有机电致器件所使用的材料可以分为顶发射、底发射或双面发射。根据本发明实施方案的有机电致器件的化合物可以有机发光器件类似的原理适用于有机太阳能电池、照明的OLED、柔性OLED、有机感光体，有机薄膜晶体管等电致器件方面。
本发明的涉及的铂，钯金属化合物都具有很好的热稳定性，本发明的涉及的铂，钯金属化合物具有较好的电子接收能力，可提升主体和客体之间的能量传输，具体表现为用本发明的铂，钯金属化合物作为功能层，尤其作为发光层制作的有机电致发光器件其电流效率提升，起亮电压降低，同时器件的寿命有较大提升，说明大部分电子和空穴复合后，能量都有效地传递给所述的铂，钯金属化合物用于发光，而非发热。
附图说明
图1为本发明有机电致发光二极管器件结构层图。
其中，110代表基板，120表示阳极，130表示空穴注入层，140表示空穴传输层， 150表示发光层，160表示空穴阻挡层，170表示电子传输层，180表示电子注入层，190表示阴极。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合具体实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
在本发明的一种优选实施方式中，本发明的OLED器件中含有空穴传输层，空穴传输材料可以优选自已知或未知的材料，特别优选地选自以下结构，但并不代表本发明限于以下结构：
Figure BDA0003155945540000071
在本发明的一种优选实施方式中，本发明的OLED器件中含有的空穴传输层，其包含一种或多种p型掺杂剂。本发明优选的p型掺杂剂为以下结构，但并不代表本发明限于以下结构：
Figure BDA0003155945540000072
本发明的一种优选实施方式中，所述的发光层可以选自以下结构中的至少一种，但并不代表本发明限于以下结构：
Figure BDA0003155945540000081
Figure BDA0003155945540000091
Figure BDA0003155945540000101
Figure BDA0003155945540000111
Figure BDA0003155945540000121
Figure BDA0003155945540000131
Figure BDA0003155945540000141
Figure BDA0003155945540000151
Figure BDA0003155945540000161
Figure BDA0003155945540000171
Figure BDA0003155945540000181
Figure BDA0003155945540000191
Figure BDA0003155945540000201
Figure BDA0003155945540000211
Figure BDA0003155945540000221
Figure BDA0003155945540000231
Figure BDA0003155945540000241
Figure BDA0003155945540000251
Figure BDA0003155945540000261
Figure BDA0003155945540000271
Figure BDA0003155945540000281
Figure BDA0003155945540000291
Figure BDA0003155945540000301
Figure BDA0003155945540000311
Figure BDA0003155945540000321
Figure BDA0003155945540000331
Figure BDA0003155945540000341
Figure BDA0003155945540000351
Figure BDA0003155945540000361
Figure BDA0003155945540000371
Figure BDA0003155945540000381
Figure BDA0003155945540000391
Figure BDA0003155945540000401
Figure BDA0003155945540000411
Figure BDA0003155945540000421
Figure BDA0003155945540000431
Figure BDA0003155945540000441
Figure BDA0003155945540000451
Figure BDA0003155945540000461
Figure BDA0003155945540000471
Figure BDA0003155945540000481
Figure BDA0003155945540000491
Figure BDA0003155945540000501
Figure BDA0003155945540000511
Figure BDA0003155945540000521
Figure BDA0003155945540000531
Figure BDA0003155945540000541
Figure BDA0003155945540000551
Figure BDA0003155945540000561
Figure BDA0003155945540000571
Figure BDA0003155945540000581
Figure BDA0003155945540000591
Figure BDA0003155945540000601
Figure BDA0003155945540000611
Figure BDA0003155945540000621
Figure BDA0003155945540000631
Figure BDA0003155945540000641
Figure BDA0003155945540000651
Figure BDA0003155945540000661
Figure BDA0003155945540000671
Figure BDA0003155945540000681
Figure BDA0003155945540000691
Figure BDA0003155945540000701
Figure BDA0003155945540000711
Figure BDA0003155945540000721
Figure BDA0003155945540000731
Figure BDA0003155945540000741
Figure BDA0003155945540000751
Figure BDA0003155945540000761
Figure BDA0003155945540000771
Figure BDA0003155945540000781
Figure BDA0003155945540000791
Figure BDA0003155945540000801
Figure BDA0003155945540000811
Figure BDA0003155945540000821
Figure BDA0003155945540000831
Figure BDA0003155945540000841
Figure BDA0003155945540000851
Figure BDA0003155945540000861
Figure BDA0003155945540000871
Figure BDA0003155945540000881
Figure BDA0003155945540000891
Figure BDA0003155945540000901
Figure BDA0003155945540000911
Figure BDA0003155945540000921
Figure BDA0003155945540000931
Figure BDA0003155945540000941
Figure BDA0003155945540000951
Figure BDA0003155945540000961
Figure BDA0003155945540000971
Figure BDA0003155945540000981
Figure BDA0003155945540000991
Figure BDA0003155945540001001
Figure BDA0003155945540001011
Figure BDA0003155945540001021
Figure BDA0003155945540001031
Figure BDA0003155945540001041
Figure BDA0003155945540001051
Figure BDA0003155945540001061
Figure BDA0003155945540001071
Figure BDA0003155945540001081
Figure BDA0003155945540001091
Figure BDA0003155945540001101
Figure BDA0003155945540001111
Figure BDA0003155945540001121
Figure BDA0003155945540001131
Figure BDA0003155945540001141
Figure BDA0003155945540001151
Figure BDA0003155945540001161
Figure BDA0003155945540001171
Figure BDA0003155945540001181
Figure BDA0003155945540001191
Figure BDA0003155945540001201
Figure BDA0003155945540001211
Figure BDA0003155945540001221
Figure BDA0003155945540001231
Figure BDA0003155945540001241
Figure BDA0003155945540001251
Figure BDA0003155945540001261
Figure BDA0003155945540001271
Figure BDA0003155945540001281
Figure BDA0003155945540001291
Figure BDA0003155945540001301
Figure BDA0003155945540001311
Figure BDA0003155945540001321
Figure BDA0003155945540001331
Figure BDA0003155945540001341
Figure BDA0003155945540001351
Figure BDA0003155945540001361
Figure BDA0003155945540001371
Figure BDA0003155945540001381
Figure BDA0003155945540001391
Figure BDA0003155945540001401
Figure BDA0003155945540001411
Figure BDA0003155945540001421
Figure BDA0003155945540001431
Figure BDA0003155945540001441
Figure BDA0003155945540001451
Figure BDA0003155945540001461
Figure BDA0003155945540001471
Figure BDA0003155945540001481
Figure BDA0003155945540001491
Figure BDA0003155945540001501
Figure BDA0003155945540001511
Figure BDA0003155945540001521
Figure BDA0003155945540001531
Figure BDA0003155945540001541
Figure BDA0003155945540001551
Figure BDA0003155945540001561
Figure BDA0003155945540001571
Figure BDA0003155945540001581
Figure BDA0003155945540001591
Figure BDA0003155945540001601
Figure BDA0003155945540001611
Figure BDA0003155945540001621
Figure BDA0003155945540001631
Figure BDA0003155945540001641
Figure BDA0003155945540001651
Figure BDA0003155945540001661
Figure BDA0003155945540001671
Figure BDA0003155945540001681
Figure BDA0003155945540001691
Figure BDA0003155945540001701
Figure BDA0003155945540001711
Figure BDA0003155945540001721
Figure BDA0003155945540001731
Figure BDA0003155945540001741
Figure BDA0003155945540001751
Figure BDA0003155945540001761
Figure BDA0003155945540001771
Figure BDA0003155945540001781
Figure BDA0003155945540001791
Figure BDA0003155945540001801
Figure BDA0003155945540001811
Figure BDA0003155945540001821
Figure BDA0003155945540001831
Figure BDA0003155945540001841
Figure BDA0003155945540001851
本发明的一种优选实施方式中，所述的电子传输层可以选自以下结构中的至少一种，但并不代表本发明限于以下结构：
Figure BDA0003155945540001861
本发明还提供一种包括所述组合物和溶剂的制剂，所用的溶剂没有特别限制，可以使用本领域技术人员熟知的例如甲苯、二甲苯、均三甲苯、四氢化萘、十氢萘、双环己烷、正丁基苯、仲丁基苯、叔丁基苯等不饱和烃溶剂、四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、溴戊烷、氯己烷、溴己烷、氯环己烷、溴环己烷等卤化饱和烃溶剂，氯苯、二氯苯、三氯苯等卤化不饱和烃溶剂，四氢呋喃、四氢吡喃等醚溶剂，苯甲酸烷基酯等酯类溶剂。所述的制剂直接用于制备光电器件。
下文中，根据已有的文献和发明人的相关技术储备，式(I)所涉及的客体化合物其通用的合成步骤如下(但并不代表本发明限于如下合成步骤)：
Figure DEST_PATH_GDA0003253958920000011
(1)在氩气保护下，将溴化物1(0.10摩尔)、硼酯1(0.10摩尔)、Pd(PPh3)4(0.005 摩尔)、K2CO3(0.4摩尔)、甲苯(400毫升)、水(100毫升)的混合溶液，加热回流16～20小时，直至取上层清液，用高效液相色谱检测溴化物1的含量＜5％，停止加热，降温至室温，用柱层析法提纯得到浅黄色粉末的配体1，收率78～88％。
(2)将K2PtCl4(2.2mmol)，配体1(2.4mmol)，CHCl3(100mL)和AcOH(100 mL)加入双口圆底烧瓶中，然后加热回流反应48小时，停止加热，降至室温，除去溶剂。将固体溶解在二氯甲烷中，过硅胶短柱。在减压条件下除去溶剂，浓缩得到的固体先后用甲醇和石油醚洗涤，得到最终目标产品，收率37～65％。结合以下实施例详细地解释了所述铂，钯金属化合物即客体化合物的制备方法以及器件的发光性能。但这些仅仅用于举例描述本发明的实施方式，所以本发明的范围并不限于此。
实施例1：化合物1的合成
Figure BDA0003155945540001881
参考通用合成路线，终产物的产率为55％。质谱m/z，理论值952.37；实测值 M+H：953.5。
实施例2：化合物2的合成
Figure BDA0003155945540001882
参考通用合成路线，终产物的产率为59％。质谱m/z，理论值1008.43；实测值 M+H：1009.6。
实施例3：化合物3的合成
Figure BDA0003155945540001883
参考通用合成路线，终产物的产率为41％。质谱m/z，理论值952.37；实测值 M+H：953.4。
实施例4：化合物4的合成
Figure BDA0003155945540001891
参考通用合成路线，终产物的产率为61％。质谱m/z，理论值946.41；实测值 M+H：947.6。
实施例5：化合物5的合成
Figure BDA0003155945540001892
参考通用合成路线，终产物的产率为46％。质谱m/z，理论值964.41；实测值 M+H：965.6。
实施例6：化合物6的合成
Figure BDA0003155945540001901
参考通用合成路线，终产物的产率为59％。质谱m/z，理论值970.36；实测值 M+H：971.5。
实施例7：化合物7的合成
Figure BDA0003155945540001902
参考通用合成路线，终产物的产率为54％。质谱m/z，理论值932.29；实测值 M+H：933.4。
实施例8：化合物8的合成
Figure BDA0003155945540001911
参考通用合成路线，终产物的产率为59％。质谱m/z，理论值970.36；实测值 M+H：971.4。
实施例9：化合物9的合成
Figure BDA0003155945540001912
参考通用合成路线，终产物的产率为44％。质谱m/z，理论值988.35；实测值 M+H：989.5。
OLED器件的制造：在发光面积为2mm×2mm大小的ITO玻璃的表面或阳极上蒸镀p掺杂材料或者将此p掺杂材料以1％～50％浓度与表中所述的化合物共蒸形成5-100nm的空穴注入层(HIL)，5-200nm的空穴传输层(HTL)，随后在空穴传输层上形成10-100nm的发光层(EML)(可含有所述的化合物)，最后依次用所述的化合物形成电子传输层(ETL)20-200nm和阴极50-200nm，如有必要在HTL 和EML层中间加入电子阻挡层(EBL)，在ETL和阴极间加入电子注入层(EIL)从而制造了有机发光元件。
OLED器件实施例：
具体实施底发射OLED器件的结构为在含有ITO的玻璃上，HIL为HT-1：P-3(95：5 v/v％)，厚度为10纳米；HTL为HT-1，厚度为90纳米；EBL为HT-10，厚度为 10纳米，EML为GH-1：有机金属配合物(94：6v/v％)，厚度为35纳米，ETL为ET-13：LiQ(50：50v/v％)，厚度为35纳米，然后蒸镀阴极Al为70纳米。
Figure BDA0003155945540001921
依据上述器件实施例，OLED器件的电流效率、操作电压、寿命等特性显示在下表1中。
表1
实施例 化合物 操作电压(伏) 电流效率(cd/A) LT90(小时)
对比器件 GD-1 3.7 68.4 150
对比器件2 GD-2 3.7 76.8 208
器件例1 化合物1 3.7 77.9 239
器件例2 化合物2 3.7 82.3 245
器件例3 化合物3 3.7 83.5 190
器件例4 化合物4 3.7 75.3 185
器件例5 化合物5 3.7 77.2 176
器件例6 化合物6 3.7 87.3 256
器件例7 化合物7 3.6 85.9 213
器件例8 化合物8 3.7 83.1 209
器件例9 化合物9 3.6 88.4 186
本发明将与对比例相比，铂或钯金属形成新型的有机金属化合物，其特点在于苯并咪唑的位置与对比例不同，发现其具有很好的发光特性，用其作为客体材料掺杂到主体材料GH-1中，获得了电流效率为75.3至88.4cd/A的OLED器件，同时器件例1，2，6，7不仅仅效率有明显的提升，同时器件的操作寿命也有不同程度的提升。通常改变取代方式会大幅度影响材料的性能，本发明给出了一个获得具有高效率、长寿命绿光掺杂材料和器件的方案。同时铂或钯金属地壳中含量丰富，有替代铱金属有机金属配合物的潜力，具有很好的商业应用前景。
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 (13)

1.一种有机金属配合物，其特征在于，所述有机金属配合物的结构如式(I)所示：
Figure FDA0003155945530000011
其中，在式(I)中，M选自铂(Pt)或钯(Pd)；X1至X3不存在、或独立地选自C-C、C＝C、C-O、C＝N、B-O、B-N、C-N、C-Si、O-Si化学键、O、S、N-R7、B-R7、P-R7、O＝P-R7、C-R7R8、C＝O、S＝O、S(＝O)2或Si-R7R8的一种；Y1至Y14独立地选自C或N或O；L1独立地选自O、N-R7、S中的一种；环CY1至环CY5各自独立地与相应的Y1至Y14组成C6～C60的环基团和C1～C50杂环基团，CY1为五元环；R1至R8各自独立地选自氢、氘、CN、卤素、羟基、肼基、脒基、酰胺基、取代或未取代的C1～C60的烷基、取代或未取代的C2～C60的烯基、取代或未取代的C1～C60的烷氧基、取代或未取代的C1～C60的环烷基、取代或未取代的C1～C60的杂烷基、取代或未取代的C6～C60的芳基、取代或未取代的C1～C60的杂芳基、取代或未取代的C1～C60的胺基、取代或未取代的C1～C60的硅基、取代或未取代的C6～C60的芳族稠环、取代或未取代的C1～C60的杂芳族稠环；R1至R8各自独立地可被部分或全部氘代、各自独立地可被部分或全氟代；R1至R8可以根据价健原则不取代或多取代。
2.根据权利要求1所述的有机金属配合物，其特征在于，与金属M相连的原子与金属M形成共价键或配位健。
3.根据权利要求1或2所述的有机金属配合物，其特征在于式(I)中的
Figure FDA0003155945530000021
部分独立选自以下代表基团的一种：
Figure FDA0003155945530000022
其中，X8独立地选自O、S、N-R7、B-R7、P-R7、O＝P-R7、C-R7R8、C＝O、S＝O、S(＝O)2或Si-R7R8的一种；Y为N或C-R9R10，R7、R8、R9、R10与权利要求1中R1所述相同。相邻的R1至R10可以成环。
4.根据权利要求1或2所述的有机金属配合物，其特征在于式(I)中的
Figure FDA0003155945530000023
部分独立地选自以下代表基团的一种：
Figure FDA0003155945530000024
其中，X8独立地选自O、S、N-R7、B-R7、P-R7、O＝P-R7、C-R7R8、C＝O、S＝O、S(＝O)2或Si-R7R8的一种；Y为N或C-R9R10，R7、R8、R9、R10与权利要求1中R1所述相同。相邻的R1至R10可以成环。
5.根据权利要求1或2所述的有机金属配合物，其特征在于式(I)中的
Figure FDA0003155945530000031
部分独立地选自以下代表基团的一种：
Figure FDA0003155945530000032
其中，R1、R2、Y1、Y2、Y5权利要求1所述相同，X8独立地选自O、S、N-R6、B-R6、P-R6、O＝P-R7、C-R7R8、C＝O、S＝O、S(＝O)2或Si-R7R8的一种；Y为N或C-R9，R7、R8、R9与权利要求1中R1所述相同，当R9为2个或多个时，彼此相同或不同，相邻的R1至R9可以成环。
6.根据权利要求1至5任一项所述的有机金属配合物，其特征在于，所述有机金属配合物式(I)选自以下代表结构的一种：
Figure FDA0003155945530000041
Figure FDA0003155945530000051
Figure FDA0003155945530000061
Figure FDA0003155945530000071
Figure FDA0003155945530000081
Figure FDA0003155945530000091
Figure FDA0003155945530000101
Figure FDA0003155945530000111
Figure FDA0003155945530000121
Figure FDA0003155945530000131
Figure FDA0003155945530000141
Figure FDA0003155945530000151
Figure FDA0003155945530000161
Figure FDA0003155945530000171
Figure FDA0003155945530000181
Figure FDA0003155945530000191
Figure FDA0003155945530000201
Figure FDA0003155945530000211
Figure FDA0003155945530000221
Figure FDA0003155945530000231
Figure FDA0003155945530000241
Figure FDA0003155945530000251
Figure FDA0003155945530000261
Figure FDA0003155945530000271
Figure FDA0003155945530000281
Figure FDA0003155945530000291
Figure FDA0003155945530000301
Figure FDA0003155945530000311
Figure FDA0003155945530000321
Figure FDA0003155945530000331
Figure FDA0003155945530000341
Figure FDA0003155945530000351
Figure FDA0003155945530000361
Figure FDA0003155945530000371
Figure FDA0003155945530000381
Figure FDA0003155945530000391
Figure FDA0003155945530000401
Figure FDA0003155945530000411
Figure FDA0003155945530000421
Figure FDA0003155945530000431
Figure FDA0003155945530000441
Figure FDA0003155945530000451
Figure FDA0003155945530000461
Figure FDA0003155945530000471
Figure FDA0003155945530000481
Figure FDA0003155945530000491
Figure FDA0003155945530000501
Figure FDA0003155945530000511
Figure FDA0003155945530000521
Figure FDA0003155945530000531
Figure FDA0003155945530000541
Figure FDA0003155945530000551
Figure FDA0003155945530000561
Figure FDA0003155945530000571
Figure FDA0003155945530000581
Figure FDA0003155945530000591
Figure FDA0003155945530000601
Figure FDA0003155945530000611
Figure FDA0003155945530000621
Figure FDA0003155945530000631
Figure FDA0003155945530000641
Figure FDA0003155945530000651
Figure FDA0003155945530000661
Figure FDA0003155945530000671
Figure FDA0003155945530000681
Figure FDA0003155945530000691
Figure FDA0003155945530000701
Figure FDA0003155945530000711
Figure FDA0003155945530000721
Figure FDA0003155945530000731
Figure FDA0003155945530000741
Figure FDA0003155945530000751
Figure FDA0003155945530000761
Figure FDA0003155945530000771
Figure FDA0003155945530000781
Figure FDA0003155945530000791
Figure FDA0003155945530000801
Figure FDA0003155945530000811
Figure FDA0003155945530000821
Figure FDA0003155945530000831
Figure FDA0003155945530000841
Figure FDA0003155945530000851
Figure FDA0003155945530000861
Figure FDA0003155945530000871
Figure FDA0003155945530000881
Figure FDA0003155945530000891
Figure FDA0003155945530000901
Figure FDA0003155945530000911
Figure FDA0003155945530000921
Figure FDA0003155945530000931
Figure FDA0003155945530000941
Figure FDA0003155945530000951
Figure FDA0003155945530000961
Figure FDA0003155945530000971
Figure FDA0003155945530000981
Figure FDA0003155945530000991
Figure FDA0003155945530001001
Figure FDA0003155945530001011
Figure FDA0003155945530001021
Figure FDA0003155945530001031
Figure FDA0003155945530001041
Figure FDA0003155945530001051
Figure FDA0003155945530001061
Figure FDA0003155945530001071
Figure FDA0003155945530001081
Figure FDA0003155945530001091
Figure FDA0003155945530001101
Figure FDA0003155945530001111
Figure FDA0003155945530001121
Figure FDA0003155945530001131
Figure FDA0003155945530001141
Figure FDA0003155945530001151
Figure FDA0003155945530001161
Figure FDA0003155945530001171
Figure FDA0003155945530001181
Figure FDA0003155945530001191
Figure FDA0003155945530001201
Figure FDA0003155945530001211
Figure FDA0003155945530001221
Figure FDA0003155945530001231
Figure FDA0003155945530001241
Figure FDA0003155945530001251
Figure FDA0003155945530001261
Figure FDA0003155945530001271
Figure FDA0003155945530001281
Figure FDA0003155945530001291
Figure FDA0003155945530001301
Figure FDA0003155945530001311
Figure FDA0003155945530001321
Figure FDA0003155945530001331
Figure FDA0003155945530001341
Figure FDA0003155945530001351
Figure FDA0003155945530001361
Figure FDA0003155945530001371
Figure FDA0003155945530001381
Figure FDA0003155945530001391
Figure FDA0003155945530001401
Figure FDA0003155945530001411
Figure FDA0003155945530001421
Figure FDA0003155945530001431
Figure FDA0003155945530001441
Figure FDA0003155945530001451
Figure FDA0003155945530001461
Figure FDA0003155945530001471
Figure FDA0003155945530001481
Figure FDA0003155945530001491
Figure FDA0003155945530001501
Figure FDA0003155945530001511
Figure FDA0003155945530001521
Figure FDA0003155945530001531
Figure FDA0003155945530001541
Figure FDA0003155945530001551
Figure FDA0003155945530001561
Figure FDA0003155945530001571
Figure FDA0003155945530001581
Figure FDA0003155945530001591
Figure FDA0003155945530001601
Figure FDA0003155945530001611
Figure FDA0003155945530001621
Figure FDA0003155945530001631
Figure FDA0003155945530001641
Figure FDA0003155945530001651
Figure FDA0003155945530001661
Figure FDA0003155945530001671
Figure FDA0003155945530001681
Figure FDA0003155945530001691
Figure FDA0003155945530001701
Figure FDA0003155945530001711
Figure FDA0003155945530001721
Figure FDA0003155945530001731
Figure FDA0003155945530001741
Figure FDA0003155945530001751
Figure FDA0003155945530001761
Figure FDA0003155945530001771
Figure FDA0003155945530001781
Figure FDA0003155945530001791
Figure FDA0003155945530001801
Figure FDA0003155945530001811
7.一种制剂，其特征在于，包含权利要求1-6任一项所述的有机金属配合物和至少一种溶剂。
8.根据权利要求7所述的一种制剂，其特征在于所述的有机金属配合物和溶剂形成制剂，所用的溶剂没有特别限制，可以使用本领域技术人员熟知的例如甲苯、二甲苯、均三甲苯、四氢化萘、十氢萘、双环己烷、正丁基苯、仲丁基苯、叔丁基苯等不饱和烃溶剂、四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、溴戊烷、氯己烷、溴己烷、氯环己烷、溴环己烷等卤化饱和烃溶剂，氯苯、二氯苯、三氯苯等卤化不饱和烃溶剂，四氢呋喃、四氢吡喃等醚溶剂，苯甲酸烷基酯等酯类溶剂。
9.一种有机光电器件，其特征在于，包括：第一电极；第二电极，与所述第一电极相面对；有机功能层，夹设于所述第一电极和所述第二电极之间；其中，有机功能层包含权利要求1至6任一项所述的有机金属配合物。
10.一种有机光电元件，包括阴极层、阳极层和有机层，该有机层包括空穴注入层、空穴传输层、发光层或活性层、电子注入层、电子传输层中至少一层，其特征在于：该器件的任一层中含有权利要求1至6所述的有机金属配合物。
11.根据权利要求9所述的有机光电元件，其特征在于，有机光电元件为有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)及有机内存器件(Organic Memory Element)、照明和显示装置。
12.根据权利要求9至11所述的有机光电元件为有机电致发光器件，其特征在于，发光层中含有所述有机金属配合物和相应的主体材料，其中所述有机金属配合物的质量百分数在1％至50％，主体材料没有任何限制。
13.一种显示或照明装置，其特征在于，所述的显示或照明装置含有权利要求9至12所述的有机光电元件。
CN202110781965.9A 2021-07-09 2021-07-09 一种有机金属配合物和及其有机光电元件 Pending CN113620996A (zh)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202110781965.9A CN113620996A (zh) 2021-07-09 2021-07-09 一种有机金属配合物和及其有机光电元件
CN202210170033.5A CN114315914B (zh) 2021-07-09 2022-02-23 有机金属配合物、制剂、有机光电器件及显示或照明装置

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110781965.9A CN113620996A (zh) 2021-07-09 2021-07-09 一种有机金属配合物和及其有机光电元件

Publications (1)

Publication Number Publication Date
CN113620996A true CN113620996A (zh) 2021-11-09

Family

ID=78379476

Family Applications (2)

Application Number Title Priority Date Filing Date
CN202110781965.9A Pending CN113620996A (zh) 2021-07-09 2021-07-09 一种有机金属配合物和及其有机光电元件
CN202210170033.5A Active CN114315914B (zh) 2021-07-09 2022-02-23 有机金属配合物、制剂、有机光电器件及显示或照明装置

Family Applications After (1)

Application Number Title Priority Date Filing Date
CN202210170033.5A Active CN114315914B (zh) 2021-07-09 2022-02-23 有机金属配合物、制剂、有机光电器件及显示或照明装置

Country Status (1)

Country Link
CN (2) CN113620996A (zh)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115181133A (zh) * 2022-07-07 2022-10-14 宇瑞(上海)化学有限公司 有机金属配合物、组合物、有机光电器件及显示或照明装置

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180045738A (ko) * 2016-10-26 2018-05-04 삼성전자주식회사 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물
KR102496480B1 (ko) * 2017-04-25 2023-02-06 삼성전자주식회사 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 조성물
KR102486392B1 (ko) * 2017-11-24 2023-01-09 삼성전자주식회사 유기 발광 소자 및 이의 제조 방법
US20190360043A1 (en) * 2018-05-23 2019-11-28 Pacific Biosciences Of California, Inc. Enrichment of dna comprising target sequence of interest
KR102626926B1 (ko) * 2018-08-31 2024-01-19 삼성전자주식회사 유기금속 화합물 및 이를 포함한 유기 발광 소자
CN112939940A (zh) * 2021-01-29 2021-06-11 浙江华显光电科技有限公司 一种有机金属配合物和含有该化合物的有机光电元件
CN112940043A (zh) * 2021-01-29 2021-06-11 浙江华显光电科技有限公司 一种有机金属配合物和含有该化合物的有机光电元件
CN112940041A (zh) * 2021-01-29 2021-06-11 浙江华显光电科技有限公司 一种有机金属配合物和含有该化合物的有机光电元件
CN112940042A (zh) * 2021-01-29 2021-06-11 浙江华显光电科技有限公司 一种有机金属配合物和含有该化合物的有机光电元件

Also Published As

Publication number Publication date
CN114315914B (zh) 2022-12-09
CN114315914A (zh) 2022-04-12

Similar Documents

Publication Publication Date Title
CN112940041A (zh) 一种有机金属配合物和含有该化合物的有机光电元件
CN112680219B (zh) 一种组合物及包含其的有机电致发光元件
CN113717232A (zh) 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN112940043A (zh) 一种有机金属配合物和含有该化合物的有机光电元件
CN112645985A (zh) 一种铱金属配合物和使用该化合物的有机光电元件
CN112724178A (zh) 一种具有氘氟协同效应的铱金属化合物及包含其的光电元件
CN114644660A (zh) 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN114315914B (zh) 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN112939940A (zh) 一种有机金属配合物和含有该化合物的有机光电元件
CN112851714A (zh) 一种铱金属配合物和使用该化合物的有机光电元件
CN112679552A (zh) 一种铱金属配合物和使用该化合物的有机光电元件
CN112920209A (zh) 一种有机金属配合物及含有该化合物的有机光电元件
CN113461736A (zh) 一种有机金属配合物和含有该化合物的有机光电元件
CN112694502A (zh) 一种铱金属配合物和使用该化合物的有机光电元件
CN112645987A (zh) 一种铱金属配合物和使用该化合物的有机光电元件
CN112679550A (zh) 一种铱金属配合物和使用该化合物的有机光电元件
CN112645988A (zh) 一种铱金属配合物和使用该化合物的有机光电元件
CN114621296B (zh) 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN114181262A (zh) 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN112940042A (zh) 一种有机金属配合物和含有该化合物的有机光电元件
CN112876518A (zh) 一种有机金属配合物和含有该化合物的有机光电元件
CN112694501A (zh) 一种铱金属配合物和使用该化合物的有机光电元件
CN112920226A (zh) 一种有机金属配合物和含有该化合物的有机光电元件
CN114773395B (zh) 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN114933616B (zh) 有机金属配合物、有机光电器件及显示或照明装置

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
WD01 Invention patent application deemed withdrawn after publication
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20211109