CN102633820B - 有机电致发光元件用化合物及有机电致发光元件 - Google Patents

有机电致发光元件用化合物及有机电致发光元件 Download PDF

Info

Publication number
CN102633820B
CN102633820B CN201210072915.4A CN201210072915A CN102633820B CN 102633820 B CN102633820 B CN 102633820B CN 201210072915 A CN201210072915 A CN 201210072915A CN 102633820 B CN102633820 B CN 102633820B
Authority
CN
China
Prior art keywords
phenyl
organic electroluminescent
electroluminescent device
pyridyl
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.)
Active
Application number
CN201210072915.4A
Other languages
English (en)
Other versions
CN102633820A (zh
Inventor
古森正树
山本敏浩
甲斐孝弘
堀田正则
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.)
Nippon Steel Chemical and Materials Co Ltd
Original Assignee
Nippon Steel Chemical 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 Nippon Steel Chemical Co Ltd filed Critical Nippon Steel Chemical Co Ltd
Publication of CN102633820A publication Critical patent/CN102633820A/zh
Application granted granted Critical
Publication of CN102633820B publication Critical patent/CN102633820B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/33—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems
    • C07C309/34—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems formed by two rings
    • C07C309/35—Naphthalene sulfonic acids
    • C07C309/36—Naphthalene sulfonic acids substituted by alkyl groups
    • C07C309/37—Naphthalene sulfonic acids substituted by alkyl groups by alkyl groups containing at least three carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic 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
    • H10K85/654—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
    • 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
    • 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
    • C09K2211/1037—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
    • C09K2211/1059—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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/311—Phthalocyanine
    • 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
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

本发明涉及一种有机电致发光元件(有机EL元件)以及其使用的化合物，所述有机电致发光元件改善元件的发光效率、充分确保驱动稳定性，且具有简单的结构。该有机电致发光元件是在被层合于基板上的阳极和阴极之间具有发光层的有机电致发光元件，该发光层含有磷光发光性掺杂剂和有机电致发光元件用化合物作为主体材料，所述有机电致发光元件用化合物具有2个以上吲哚咔唑骨架。其使用的吲哚咔唑化合物可例示如下述式表示的化合物。

Description

有机电致发光元件用化合物及有机电致发光元件
本专利申请为在2006年11月22日提出申请的专利申请号为200680045030.8、名称为“有机电致发光元件用化合物及有机电致发光元件”的专利申请的分案申请。
技术领域
本发明涉及一种新的有机电致发光元件用化合物及有机电致发光元件(以下称为有机EL元件)，详细地来讲，涉及一种通过并用磷光发光掺杂剂和具有特定结构的主体化合物而显示高亮度的有机EL元件。
背景技术
通常，有机EL元件，作为其最简单的结构是由发光层及夹持该层的一对对置电极构成。即，在有机EL元件中，利用的是如下现象，即当在两个电极间施加电场时，从阴极注入电子，从阳极注入空穴，它们在发光层中，在复合能级从传导带返回到价电子带时作为能量发出光。
近年来，对使用了有机薄膜的EL元件进行了开发。特别是为了提高发光效率，通过以下元件的开发，即，为了提高从电极注入载流子的效率而对电极的种类进行最佳化，在电极间作为薄膜设置由芳香族二胺形成的空穴输送层和由8-羟基喹啉铝配合物(以下称为Alq3)形成的发光层，由此与现有的使用蒽等的单晶的元件相比，发光效率得到了大幅度的改善，因此，以实用于具有自发光·高速应答性的特征的高性能平板为目标取得了进展。
另外，作为提高元件的发光效率的尝试，还正在对不使用荧光而使用磷光进行研究。以上述的设置有由芳香族二胺形成的空穴输送层和由Alq3形成的发光层的元件为代表的许多元件利用的是荧光发光，但是，如果使用磷光发光、即利用来自三重激发态的发光，则与目前使用荧光(单态)的元件相比，可期待3倍左右的效率提高。为了这个目的，对将香豆素衍生物、二苯甲酮衍生物作为发光层进行了研究，但只得到非常低的亮度。其后，作为利用三重态的尝试，对使用铕配合物进行了研究，但其也达不到高效率的发光。作为磷光发光掺杂剂，多数进行的是如特表2003-515897号公报(专利文献1)所例举的发明。
专利文献1：特表2003-515897号公报
专利文献2：特开2001-313178号公报
专利文献3：特开2002-305083号公报
专利文献4：特开2002-352957号公报
专利文献5：特开平11-162650号公报
专利文献6：特开平11-176578号公报
在有机EL元件开发中，作为用于发光层的主体材料而提出的方案是特开2001-313178号公报中介绍的咔唑化合物的CBP。如果使用CBP作为绿色磷光发光材料的三(2-苯基吡啶)铱配合物(以下称为Ir(ppy)3)的主体材料，由于CBP容易使空穴流动而难以使电子流动的特性，电荷注入平衡瓦解，过剩的空穴流出至电子输送侧，结果来自Ir(ppy)3的发光效率下降。
作为上述的解决手段，有例如如特开2002-305083号公报那样在发光层和电子输送层间设置空穴阻挡层的手段。通过该空穴阻挡层将空穴高效率地积蓄在发光层中，由此可以提高和发光层中的电子的复合几率，达到发光的高效率化。作为目前通常使用的空穴阻挡材料，可例举2，9-二甲基-4，7-二苯基-1，10-菲咯啉(以下称为BCP)及对苯基苯酚-二(2-甲基-8-羟基喹啉-N1，08)铝(以下称为BAlq)。由此可以防止在电子输送层电子和空穴发生复合，但由于BCP即使在室温下也容易结晶，欠缺作为材料的可靠性，因此元件寿命极其短。另外，报告有BAlq的Tg为约100℃和比较良好的元件寿命结果，但空穴阻挡能力不充分，来自Ir(ppy)3的发光效率下降。
另一方面，特开2002-352957号公报中介绍的3-苯基-4-(1’-萘基)-5-苯基-1，2，4-三唑(以下称为TAZ)也被提出作为磷光有机EL元件的主体材料，但由于容易使电子流动而难以使空穴流动的特性，发光领域成为空穴输送层侧，因此也可以认为，因空穴输送层的材料而导致与Ir(ppy)3的相容性问题，由此来自Ir(ppy)3的发光效率下降。例如，从高性能、高可靠性、长寿命的观点考虑，作为空穴输送层最好使用的4，4’-双(N-(1-萘基)-N-苯氨基)联苯(以下称为NPB)存在的问题如下，即其与Ir(ppy)3的相容性差，从Ir(ppy)3向NPB发生能量转换，发光效率下降。
另外，特开平11-162650号公报及特开平11-176578号公报中对吲哚咔唑化合物进行了公开，但关于本发明的化合物没有公开。另外，特开平11-162650号公报及特开平11-176578号公报中公开的吲哚咔唑化合物被推荐作为空穴输送材料的使用，还强调了化合物的稳定性，但并没有教导作为磷光主体材料的使用。
发明内容
为了将有机EL元件应用于平板显示器等的显示元件，必须在改善元件的发光效率的同时充分确保驱动时的稳定性。本发明，鉴于上述现状，目的在于提供一种高效率且具有高驱动稳定性的实用上有用的有机EL元件以及适合其的化合物。
本发明人等进行了潜心研究，结果发现，通过将具有特定的吲哚咔唑骨架的化合物使用于有机EL元件可以解决上述问题，以至完成了本发明。
本发明的有机电致发光元件用化合物由下述通式(1)表示。
在此，Z表示由不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基组成的连接基团，
n表示2以上的整数，
Y表示下述式(1a)表示的基团；
在此，
环A表示和相邻环缩合的式(1b)表示的芳香族环或杂环，
环B表示和相邻环缩合的式(1c)表示的杂环，
X表示碳或氮，
R43表示氢、不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基、或和含有X的环缩合的环，
R44表示不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基，
R41、R42表示氢、烷基、芳烷基、链烯基、炔基、氰基、二烷基氨基、二芳基氨基、二芳烷基氨基、氨基、硝基、酰基、烷氧基羰基、羧基、烷氧基、烷基磺酰基、卤代烷基、羟基、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。
在通式(1)中，当Y为下述式(1d)表示的基团时，可得到优异的有机电致发光元件用化合物。或者，当n为2、3或4时，可得到优异的有机电致发光元件用化合物。
在此，
R45表示氢、不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基，
R46具有和R44相同的含义，
R47、R48独立地具有和R41相同的含义。
另外，通式(1)表示的本发明的有机电致发光元件用化合物有下述通式(2)或(3)表示的化合物。
在此，
环A、环A’表示和相邻环缩合的式(2a)表示的芳香环，
环B、环B’表示和相邻环缩合的式(2b)表示的杂环。
在此，
环C、环C’表示和相邻环缩合的式(3a)表示的芳香环，
环D、环D’表示和相邻环缩合的式(3b)表示的杂环，
环E、环E’表示和相邻环缩合的式(3c)表示的杂环。
而且，本发明的有机电致发光元件用化合物有下述通式(4)或(5)表示的化合物。
在此，
环F、环F’表示和相邻环缩合的式(5a)表示的杂环。
在上述通式(2)～(5)及式(2a)～(2c)、(3a)～(3c)、(5a)中，当环A、A’、C、C’为苯环、R6、R14、R15、R22、R23、R30、R31、R32为取代或未取代的苯基或吡啶基、且R1～R4、R7～R12、R16～R21、R24～R29为氢或苯基时，可得到优异的有机电致发光元件用化合物。
在上述通式(1)～(5)及式(1a)～(1d)、(2a)～(2c)、(3a)～(3c)、(5a)中，记号具有以下的意义。
X表示碳或氮，
R5、R13、R17、R20、R45独立地表示氢、不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基，
R6、R14～R15、R22～R23、R30～R32、R44、R46独立地表示不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基，
Ar1～Ar4独立地表示由不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基组成的2价的连接基团，
R1～R4、R7～R12、R16、R18～R19、R21、R24～R29、R41～R42、R47～R48独立地表示烷基、芳烷基、链烯基、炔基、氰基、二烷基氨基、二芳基氨基、二芳烷基氨基、氨基、硝基、酰基、烷氧基羰基、羧基、烷氧基、烷基磺酰基、卤代烷基、羟基、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。
另外，本发明为在被层合于基板上的阳极和阴极之间具有发光层的有机电致发光元件，其特征在于，该发光层含有磷光发光性掺杂剂和上述有机电致发光元件用化合物作为主体材料。希望该有机电致发光元件在阳极和发光层之间具有空穴注入输送层以及在阴极和发光层之间具有电子注入输送层。或者希望在发光层和电子注入输送层之间具有空穴阻挡层。
在本发明中，将上述通式(1)表示的化合物、优选通式(2)～(5)表示的化合物的任一种以上用于有机EL元件中的至少一个有机层中。
本发明的有机EL元件用化合物由上述通式(1)表示。通式(1)中，Z表示选自不是稠环结构的取代或未取代的芳香族烃基及不是稠环结构的取代或未取代的芳香族杂环基的连接基团。n表示2以上的整数。而且，Z是n价的基团。
在连接基团Z为芳香族烃基时，作为形成芳香族烃基的芳香族烃环，可优选例举苯环、联苯环、三联苯环等。在为芳香族杂环基时，可优选例举吡啶环、三唑环、二唑环、苯基吡啶环、苯基三唑环、三苯基三唑环等。当这些基团具有取代基时，作为取代基可优选例举碳数1～6的烷基、苯基、吡啶基等。取代基的数以0～4、优选0～2为宜。
Y为上述式(1a)表示的基团。式(1a)中，环A及环B表示和相邻环缩合的环。有利的是Y为上述通式(1d)表示的基团。
在R41、R42为取代或未取代的芳香族烃基或芳香族杂环基时，作为芳香族烃基可优选例举苯基、联苯基等。在为芳香族杂环基时，可优选例举吡啶基。当这些基团具有取代基时，作为取代基可优选例举碳数1～6的烷基、苯基、吡啶基等。取代基的个数以0～4、优选0～2为宜。
在R43或R44为芳香族烃基时，作为芳香族烃基可优选例举苯基、联苯基等。在为芳香族杂环基时，可优选例举吡啶基。当这些基团具有取代基时，作为取代基可例举碳数1～6的烷基、苯基、吡啶基等。取代基的个数以0～4、优选0～2为宜。R43除了可以为上述芳香族烃基或芳香族杂环基以外，还可以为氢或和式(1b)中的含有X的6元环缩合的环，优选为氢或上述环。
在为和式(1b)中的含有X的6元环缩合的环时，该环也可以是稠合环。作为其为稠合环时的例子，有通式(3)及(5)中的具有稠合环的环E、E’及环F、F’。即，优选也可以具有R9、R12、R25或R28的吲哚环。此时，吲哚环中的含氮环与含有X的6元环缩合。
在通式(1)中，由于环A为苯环时成为吲哚咔唑衍生物，因此，本发明的化合物可以称为具有吲哚咔唑单元的化合物。该吲哚咔唑单元是提高空穴输送性的单元，为了进一步提高空穴输送性，n必须为2以上。需要说明的是，对于通式(1)而言，由于通式(1)的化合物包括通式(2)～(5)表示的化合物，因此，在称为通式(1)的化合物时，可理解为含有这些式子表示的化合物的意思。
n优选为2～4，更优选为2～3。n为5以上时，分子量变大，升华性下降，在制作电致发光元件时，有时候在使用蒸镀法的情况下发生障碍或因杂质的高分子量升高而导致难以提纯。
作为n为2的通式(1)所含的化合物有通式(2)～(5)表示的化合物。通式(2)～(5)中出现具有和通式(1)相同含义的记号，优选为与通式(1)所述的同样的基团或环。
对本发明的有机EL元件而言，在层合于基板上的阳极和阴极之间具有发光层，该发光层含有磷光发光性掺杂剂和上述有机EL用化合物作为主体材料。有利的是在阳极和发光层之间具有空穴注入输送层以及在阴极和发光层之间具有电子注入输送层。另外，在发光层和电子注入输送层之间具有空穴阻挡层也是有利的。
更有利的是，本发明的有机EL元件，可以使用在上述通式(1)中Y为通式(1d)表示的化合物或通式(2)～(5)表示的化合物作为主体材料。
通式(1)表示的化合物可以用公知的方法容易地制造。例如，以Tetrahedron，1991，Vol.47，No.37，p7739-7750所示的合成例作为参考，可以通过以下的反应式来制造。
通式(2)表示的化合物可以通过以下的反应式来制造。
另外，通式(1)中，Y为通式(1d)、n＝3的化合物可以通过以下的反应式来制造。
通式(2)～(5)中的Ar1～Ar4表示2价的连接基团。具体而言可例举以下的Y-1～Y-118表示的连接基团。
另外，这些连接基团也可以具有取代基。作为取代基的例子可例举烷基、芳烷基、链烯基、炔基、氰基、二烷基氨基、二芳基氨基、二芳烷基氨基、氨基、硝基、酰基、烷氧基羰基、羧基、烷氧基、烷基磺酰基、卤代烷基、羟基、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。
作为取代基的优选例子，可例举以下的Z-1～Z-138表示的取代基。
上述通式(2)～(5)表示的化合物的优选具体例如下所示，但并不限于此。
上述通式(1)表示的Y为通式(1d)、n为3以上的有机EL元件用化合物的优选具体例如下所示，但并不限于此。
本发明的有机EL元件，在发光层中含有磷光发光性掺杂剂和上述有机EL用化合物作为主体材料。作为发光层中的磷光发光掺杂剂材料，可以含有包含选自钌、铑、钯、银、铼、锇、铱、铂及金中的至少一种金属的有机金属配合物。该有机金属配合物在上述专利文献等中是公知的，可以对它们进行选择使用。
作为优选的磷光发光掺杂剂，可例举具有Ir的等贵金属元素作为中心金属的Ir(ppy)3等的配合物类、Ir(bt)2·acac3等的配合物类、PtOEt3等的配合物类。这些配合物类的具体例如下所示，但不限定于下述的化合物。
上述磷光发光掺杂剂在发光层中所含有的量优选为5～10重量％的范围。
本发明的有机EL元件是在层合于基板上的阳极和阴极之间具有至少一个的发光层的有机EL元件，该发光层含有磷光发光性掺杂剂和通式(1)表示的化合物。
附图说明
图1是表示有机EL元件的一个实例的示意图。
符号的说明
1  基板
2  阳极
3  空穴注入层
4  空穴输送层
5  发光层
6  电子输送层
7  阴极
具体实施方式
下面，对于本发明的有机EL元件的结构，一边参照附图一边进行说明，但是本发明的有机EL元件的结构不受这些图示的任何限制。
图1是示意地表示在本发明中使用的通常的有机EL元件的结构例的剖示图，1表示基板、2表示阳极、3表示空穴注入层、4表示空穴输送层、5表示发光层、6表示电子输送层、7表示阴极。在本发明的有机EL元件中，具有基板、阳极、发光层及阴极作为必须的层，但除了必须的层以外，可具有空穴注入输送层、电子注入输送层，还可在发光层和电子注入输送层之间具有空穴阻挡层。需要说明的是，空穴注入输送层是指空穴注入层和空穴输送层的任一层或这两层，电子注入输送层是指电子注入层和电子输送层的任一层或这两层。
需要说明的是，也可以是和图1相反的结构，即，在基板1上依次层合阴极7、电子输送层6、发光层5、空穴输送层4、阳极2，如上所述，还可以在至少一个基板的透明性高的2个基板间设置本发明的有机EL元件。此时，也可以根据需要追加层或省略层。
本发明的有机EL元件可以适用于单一元件、含有以阵列状配置成的结构的元件、阳极和阴极以X-Y矩阵状配置成的结构的任一种。根据本发明的有机EL元件，通过使发光层含有具有特定的骨架的化合物和磷光发光掺杂剂，可得到与目前使用来自单态的发光的元件相比发光效率高、且驱动稳定性也得到大大改善的元件，可以在全色或多彩面板的应用中发挥优异性能。
实施例
以下，通过实施例更详细说明本发明，但本发明并不限于这些实施例，可以以各种形式进行实施。需要说明的是，化合物编号为对上述化学式赋予的编号。
实施例1
(化合物9的合成)
在进行脱气氮气置换了的200ml三口烧瓶中，加入1，2-环己二酮5.0g(44.59mmol)、苯肼盐酸盐12.9g(89.21mmol)，在其中加入乙醇145ml，进行搅拌。然后，在同一烧瓶内用5分钟滴加浓硫酸0.45g(4.59mmo l)。然后加热至65℃，搅拌4小时。冷却至室温后，滤取生成的紫褐色结晶后，将滤取的结晶用乙醇50ml进行两次再淤浆化洗涤(reslurried)。对其进行减压干燥，得到紫褐色粉末12.0g(43.59mmo l、收率97.7％)。
接着，在300ml三口烧瓶中，加入上述紫褐色粉末12.0g(43.59mmol)，在其中加入乙酸140g、三氟乙酸8.0g，进行搅拌。然后加热至100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用乙酸200ml进行漂洗洗涤后，用己烷200ml进行漂洗洗涤。对其进行减压干燥，得到白色粉末5.0g(19.51mmol、收率44.4％)。
在进行脱气氮气置换了的200ml三口烧瓶中，加入上述得到的白色粉末4.0g(15.61mmol)、4，4’-二碘联苯3.2g(7.88mmol)、碘化铜7.6g(39.91mmol)、碳酸钾9.7g(70.18mmol)，在其中加入喹啉150ml，进行搅拌。然后加热至190℃，搅拌24小时。暂时冷却至室温后，加入碘代苯40.0g(196.07mmol)、碘化铜7.6g(39.91mmol)，加热至190℃，搅拌3天。冷却至室温后，加入水200ml、二氯甲烷200ml，进行搅拌后，滤取生成的黄色结晶。将滤液转移到1000ml分液漏斗，分馏为有机层和水层。将有机层用200ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到白色固体(化合物9)3.0g(3.69mmol、收率46.8％)。
化合物9的EI-MS(M+1)为814、熔点为398℃。
实施例2
(化合物40的合成)
在进行脱气氮气置换了的2000ml三口烧瓶中，加入1，2-环己二酮33.3g(297.0mmol)、苯肼盐酸盐86.0g(594.7mmol)，在其中加入乙醇1000ml，进行搅拌。然后，用5分钟在同一烧瓶内滴加浓硫酸3.0g(30.6mmol)。然后加热至65℃，搅拌4小时。冷却至室温后，滤取生成的紫褐色结晶后，将滤取的结晶用乙醇500ml进行两次再淤浆化洗涤。对其进行减压干燥，得到紫褐色粉末80.0g(280.5mmol、收率96.3％)。
接着，在1000ml三口烧瓶中，加入上述紫褐色粉末72.0g(261.5mmol)，在其中加入乙酸720g、三氟乙酸72.0g，进行搅拌。然后加热至100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用乙酸200ml进行漂洗洗涤后，用己烷200ml进行漂洗洗涤。对其进行减压干燥，得到白色粉末30.0g(117.1mmol、收率44.8％)。
接着，在进行脱气氮气置换了的1000ml三口烧瓶中，加入上述得到的白色粉末26.0g(101.4mmol)、碘代苯122.7g(601.4mmol)、碘化铜54.7g(287.2mmol)、碳酸钾66.7g(482.6mmol)，在其中加入喹啉800ml，进行搅拌。然后加热至190℃，搅拌72小时。暂时冷却至室温后，加入水500ml、二氯甲烷500ml，进行搅拌后，滤取生成的黄色结晶。将滤液转移到2000ml分液漏斗，分馏为有机层和水层。将有机层用500ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到白色固体13.7g(41.2mmol、收率40.6％)。
接着，在进行脱气氮气置换了的500ml三口烧瓶中，加入55％氢化钠2.16g(49.5mmol)、脱水N，N’-二甲基甲酰胺70ml，在氮气流中进行搅拌。在上述得到的白色粉末13.7g(41.2mmol)中加入脱水N，N’-二甲基甲酰胺70ml，使其溶解，然后用15分钟滴加在同一烧瓶内。滴加结束后，继续搅拌1小时。然后，在氰尿酰氯3.76g(20.4mmol)中加入脱水N，N’-二甲基甲酰胺70ml，使其溶解，然后用15分钟滴加在同一烧瓶内。滴加结束后，继续搅拌2小时，然后，加入水350g，滤取析出的结晶。将滤取的结晶用水300g进行两次再淤浆化，然后用甲醇300g进行再淤浆化。对其进行减压干燥后，用柱色谱法进行提纯，得到白色粉末10.9g(14.0mmol、收率70.0％)。
接着，在300ml三口烧瓶中，加入上述得到的白色粉末10.0g(12.9mmol)、苯基硼酸2.0g(16.4mmol)、四(三苯基膦)钯(0)1.5g(1.3mmol)、乙醇50ml、甲苯100ml，进行搅拌。然后，使碳酸钠6.5g(47.0mmol)溶解于水50ml，加在同一烧瓶内，加热至85℃，搅拌5小时。暂时冷却至室温后，加入水100ml、甲苯100ml，进行搅拌后，暂时过滤分离不溶物。将滤液转移到1000ml分液漏斗，分馏为有机层和水层。将有机层用100ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到黄色固体5.3g(6.5mmol、收率50.2％)。
化合物40的EI-MS(M+1)为818、熔点未测出。
实施例3
(化合物27的合成)
在进行脱气氮气置换了的2000ml三口烧瓶中，加入1，2-环己二酮33.3g(297.0mmol)、苯肼盐酸盐86.0g(594.7mmol)，在其中加入乙醇1000ml，进行搅拌。然后，用5分钟在同一烧瓶内滴加浓硫酸3.0g(30.6mmol)。然后加热至65℃，搅拌4小时。冷却至室温后，滤取生成的紫褐色结晶后，将滤取的结晶用乙醇500ml进行两次再淤浆化洗涤。对其进行减压干燥，得到紫褐色粉末80.0g(280.5mmol、收率96.3％)。
接着，在1000ml三口烧瓶中，加入上述紫褐色粉末72.0g(261.5mmol)，在其中加入乙酸720g、三氟乙酸72.0g，进行搅拌。然后加热至100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用乙酸200ml进行漂洗洗涤后，用己烷200ml进行漂洗洗涤。对其进行减压干燥，得到白色粉末30.0g(117.1mmol、收率44.8％)。
接着，在进行脱气氮气置换了的1000ml三口烧瓶中，加入上述得到的白色粉末26.0g(101.4mmol)、碘代苯122.7g(601.4mmol)、碘化铜54.7g(287.2mmol)、碳酸钾66.7g(482.6mmol)，在其中加入喹啉800ml，进行搅拌。然后加热至190℃，搅拌72小时。暂时冷却至室温后，加入水500ml、二氯甲烷500ml，进行搅拌后，滤取生成的黄色结晶。将滤液转移到2000ml分液漏斗，分馏为有机层和水层。将有机层用500ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到白色固体13.7g(41.2mmol、收率40.6％)。
接着，在进行脱气氮气置换了的2000ml三口烧瓶中，加入上述得到的白色粉末13.7g(41.2mmol)、6，6’-二溴-2，2’-联二吡啶6.4g(20.4mmol)、碘化铜1.14g(5.98mmol)、磷酸三钾25.22g(118.8mmol)，其中加入1，4-二烷200ml，进行搅拌。一边继续搅拌一边加入tranc-1，2-环己二胺10ml。然后，加热至115℃，搅拌15小时。暂时冷却至室温后，滤取不溶物。将滤液减压蒸馏除去后，加入甲醇，滤取析出的白色固体。然后，用柱色谱法进行提纯，得到白色固体5.0g(6.14mmol、收率30.0％)。
化合物27的EI-MS(M+1)为816、熔点为362℃。
实施例4
在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从蒸镀源蒸镀化合物9，以/秒形成50nm厚的薄膜。用荧光测定装置评价作成的薄膜。
接着，在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从不同的蒸镀源蒸镀化合物9和Ir(ppy)3，以/秒形成50nm厚的Ir(ppy)3的浓度为7.0％的薄膜。
用荧光测定装置评价作成的薄膜。激发波长使用化合物9的极大吸收波长，观察此时发出的光，与单独化合物9的薄膜的情况下发出的光进行比较。结果示于表1。
实施例5
在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从蒸镀源蒸镀化合物40，以/秒形成50nm厚的薄膜。用荧光测定装置评价作成的薄膜。
接着，在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从不同的蒸镀源蒸镀化合物40和Ir(ppy)3，以/秒形成50nm厚的Ir(ppy)3的浓度为7.0％的薄膜。
用荧光测定装置评价作成的薄膜。激发波长使用化合物40的极大吸收波长，观察此时发出的光，并与单独化合物40的薄膜的情况下发出的光进行比较。结果示于表1。
实施例6
在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从蒸镀源蒸镀化合物27，以/秒形成50nm厚的薄膜。用荧光测定装置评价作成的薄膜。
接着，在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从不同的蒸镀源蒸镀化合物27和Ir(ppy)3，以/秒形成50nm厚的Ir(ppy)3的浓度为7.0％的薄膜。
用荧光测定装置评价作成的薄膜。激发波长使用化合物27的最大吸收波长，观察此时发出的光，并与单独化合物27的薄膜的情况下发出的光进行比较。结果示于表1。
比较例1
除将薄膜主要成分变更为Alq3作成薄膜以外，和实施例4同样进行。结果示于表1。由表1可知，在发光层的主要材料使用化合物9、40及27时，Ir(ppy)3发生能量转换，可观察到来自Ir(ppy)3的发光，但使用Alq3时，Ir(ppy)3没有发生能量转换，Alq3自身发出荧光。
[表1]
实施例7
在图1中，作成省略了空穴注入层、追加了电子注入层的构成的有机EL元件。在形成有膜厚150nm的由I TO形成的阳极的玻璃基板上，利用真空蒸镀法，在真空度4.0×10-4Pa下使各薄膜层合。首先，在ITO上形成60nm厚的NPB作为空穴输送层。
接着，在空穴输送层上，作为发光层，从不同的蒸镀源共蒸镀化合物9和Ir(ppy)3，形成25nm厚。此时，Ir(ppy)3的浓度为7.0％。接着，形成50nm厚的Alq3作为电子输送层。进而，在电子输送层上，形成0.5nm厚的氟化锂(LiF)作为电子注入层。最后，在电子注入层上，形成170nm厚的铝(Al)作为电极，作成有机EL元件。
实施例8
在图1中，作成省略了空穴注入层、追加了电子注入层的构成的有机EL元件。在形成有膜厚150nm的由ITO形成的阳极的玻璃基板上，利用真空蒸镀法，在真空度4.0×10-4Pa下使各薄膜层合。首先，在ITO上形成60nm厚的NPB作为空穴输送层。
接着，在空穴输送层上，作为发光层从不同的蒸镀源共蒸镀化合物40和Ir(ppy)3，形成25nm厚。此时，Ir(ppy)3的浓度为7.0％。接着，形成50nm厚的Alq3作为电子输送层。进而，在电子输送层上，形成0.5nm厚的氟化锂(LiF)作为电子注入层。最后，在电子注入层上，形成170nm厚的铝(Al)作为电极，作成有机EL元件。
实施例9
在图1中，作成省略了空穴注入层、追加了电子注入层的构成的有机EL元件。在形成有膜厚150nm的由ITO形成的阳极的玻璃基板上，利用真空蒸镀法，在真空度4.0×10-4Pa下使各薄膜层合。首先，在ITO上形成60nm厚的NPB作为空穴输送层。
接着，在空穴输送层上，作为发光层，从不同的蒸镀源共蒸镀化合物27和Ir(ppy)3，形成25nm厚。此时，Ir(ppy)3的浓度为7.0％。接着，形成50nm厚的Alq3作为电子输送层。进而，在电子输送层上，形成0.5nm厚的氟化锂(LiF)作为电子注入层。最后，在电子注入层上，形成170nm厚的铝(Al)作为电极，作成有机EL元件。
在得到的有机EL元件上连接外部电源，施加直流电压，可以确认具有表2所示的发光特性。在表2中，亮度、电压及发光效率表示在10mA/cm2下的值。予以说明的是，已知元件发光光谱的极大波长为517nm，可得到来自Ir(ppy)3的发光。
比较例2
除使用HMTPD作为空穴输送层、使用TAZ作为发光层的主成分以外，和实施例7同样进行地作成有机EL元件。
比较例3
除使用TAZ作为发光层的主成分以外，和实施例7同样地作成有机EL元件。
[表2]
实施例10
(化合物103的合成)
在进行脱气氮气置换了的200ml三口烧瓶中，加入1，2-环己二酮33.3g(0.297mol)、苯肼盐酸盐86.0g(0.595mol)，在其中加入乙醇1000ml，进行搅拌。然后，用5分钟在同一烧瓶内滴加浓硫酸3.0g(0.03mol)。然后加热至65℃，搅拌4小时。冷却至室温后，滤取生成的紫褐色结晶后，将滤取的结晶用乙醇500ml进行两次再淤浆化洗涤。对其进行减压干燥，得到紫褐色粉末80.0g(0.286mol、收率96.3％)。
接着，在上述紫褐色粉末72.0g(0.258mol)中加入乙酸720g、三氟乙酸72.0g，进行搅拌。然后加热至100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用乙酸200ml进行漂洗洗涤后，用己烷200ml进行漂洗洗涤。对其进行减压干燥，得到白色粉末30.0g(0.117mol、收率45.3％)。
接着，在进行脱气氮气置换了的1000ml三口烧瓶中，加入上述得到的白色粉末26.0g(0.101mol)、碘代苯122.7g(0.601mol)、碘化铜54.7g(0.287mol)、碳酸钾66.7g(0.482mol)，在其中加入喹啉800ml，进行搅拌。然后加热至190℃，搅拌72小时。暂时冷却至室温后，加入水500ml、二氯甲烷500ml，进行搅拌后，滤取生成的黄色结晶。将滤液转移到2000ml分液漏斗，分馏为有机层和水层。将有机层用500ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到白色固体13.7g(0.04mol、收率40.8％)。
接着，在进行脱气氮气置换了的500ml三口烧瓶中，加入55％氢化钠2.16g(49.5mmol)、脱水N，N’-二甲基甲酰胺70ml，在氮气流中进行搅拌。在上述得到的白色粉末13.7g(40mmol)中加入脱水N，N’-二甲基甲酰胺70ml，使其溶解，然后用15分钟滴加在同一烧瓶内。滴加结束后，继续搅拌1小时。然后，在氰尿酰氯2.46g(13mmol)中加入脱水N，N’-二甲基甲酰胺70ml，使其溶解，然后用15分钟滴加在同一烧瓶内。滴加结束后，在内温为80℃下继续搅拌24小时后，冷却至室温。冷却后，在同一烧瓶内加入水350g，滤取析出的结晶。将滤取的结晶用水300g进行两次再淤浆化，然后用甲醇300g进行再淤浆化。对其进行减压干燥后，用柱色谱法进行提纯，得到淡黄色粉末2.1g(2.0mmol、收率15.5％)。
化合物103的EI-MS(M+1)为1072、熔点为492℃。
实施例11
在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从蒸镀源蒸镀化合物103，以/秒形成50nm厚的薄膜。用荧光测定装置评价作成的薄膜。接着，在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从不同的蒸镀源蒸镀化合物3和Ir(ppy)3，以秒形成50nm厚的Ir(ppy)3的浓度为7.0％的薄膜。
用荧光测定装置评价作成的薄膜。激发波长使用化合物103的极大吸收波长，观察此时发出的光，并与单独化合物103的薄膜的情况下发出的光进行比较。结果示于表3。
比较例4
除将薄膜主成分变更为Alq3作成薄膜以外，和实施例11同样进行。结果示于表3。
[表3]
实施例12
在图1中，作成省略了空穴注入层、追加了电子注入层的构成的有机EL元件。在形成有膜厚150nm的由ITO形成的阳极的玻璃基板上，利用真空蒸镀法，在真空度4.0×10-4Pa下使各薄膜层合。首先，在ITO上形成60nm厚的NPB作为空穴输送层。
接着，在空穴输送层上，作为发光层从不同的蒸镀源共蒸镀化合物103和Ir(ppy)3，形成25nm厚。此时，Ir(ppy)3的浓度为7.0％。接着，形成50nm厚的Alq3作为电子输送层。进而，在电子输送层上，形成0.5nm厚的氟化锂(LiF)作为电子注入层。最后，在电子注入层上，形成170nm厚的铝(Al)作为电极，作成有机EL元件。
在得到的有机EL元件上连接外部电源、施加直流电压，结果可以确认具有表4所示的发光特性。在表4中，亮度、电压及发光效率表示在10mA/cm2下的值。予以说明的是，已知元件发光光谱的极大波长为517nm，可得到来自Ir(ppy)3的发光。
比较例5
除使用HMTPD作为空穴输送层、使用TAZ作为发光层的主成分以外，和实施例12同样地作成有机EL元件。
比较例6
除使用TAZ作为发光层的主成分以外，和实施例12同样地作成有机EL元件。
[表4]
产业上的可利用性
本发明的有机EL元件可以在低电压下以高亮度·高效率进行发光。因此可以认为，本发明的有机EL元件应用于平板显示器(例如OA计算机用或壁挂式电视)、车载显示元件、利用了作为手提电话显示或面发光体的特征的光源(例如复印机的光源、液晶显示器、仪表类的背光光源)、显示板、指示灯，其技术价值大。

Claims (9)

1.有机电致发光元件用化合物，其由下述通式(2)表示，
式中，环A、环A’表示和相邻环缩合的式(2a)表示的芳香环，
环B、环B’表示和相邻环缩合的式(2b)表示的杂环，
Ar1为未取代的或碳数1-6的烷基、苯基或吡啶基取代的、取代基的数为0-4的以下Y-7、Y-26～Y-44的连接基团；
X表示碳，
R5表示氢、未取代的或碳数1-6的烷基、苯基、吡啶基取代的、取代基的数0-4的苯基、联苯基、或吡啶基，
R6表示未取代的或碳数1-6的烷基、苯基、吡啶基取代的、取代基的数0-4的苯基、联苯基、或吡啶基，
R1～R4独立地表示氢、未取代的或碳数1-6的烷基、苯基、或吡啶基取代的、取代基的数0-4的苯基、联苯基、或吡啶基，
2.权利要求1所述的有机电致发光元件用化合物，其由下述通式(4)表示，
式中，Ar3为与通式(2)中的Ar1的含义相同；
R17、R20与通式(2)中的R5的含义相同；
R22、R23与通式(2)中的R6的含义相同；
R16、R18、R19、R21表示氢、未取代的或碳数1-6的烷基、苯基、或吡啶基取代的、取代基的数0-4的苯基、联苯基、或吡啶基，
3.权利要求1所述的有机电致发光元件用化合物，其中通式(2)及式(2a)～(2b)中，环A、环A’为苯环，R6为未取代的或碳数1-6的烷基、苯基或吡啶基取代的、取代基的数为0-4的苯基或吡啶基，且R1-R4为氢或苯基。
4.权利要求2所述的有机电致发光元件用化合物，其中通式(4)中，R22～R23为未取代的、或碳数1-6的烷基、苯基或吡啶基取代的、取代基的数为0-4的苯基或吡啶基，且R16～R21为氢或苯基。
5.权利要求1所述的有机电致发光元件用化合物，其中通式(2)的Ar1为由以下的Y-7或Y-28表示连接基团，
6.如权利要求1所述的有机电致发光元件用化合物，其中，通式(2)表示的有机电致发光元件用化合物，选自以下的化合物：
7.一种有机电致发光元件，其是在层合于基板上的阳极和阴极之间具有发光层的有机电致发光元件，其中，该发光层含有磷光发光性掺杂剂和权利要求1～6中任一项所述的有机电致发光元件用化合物作为主体材料。
8.如权利要求7所述的有机电致发光元件，其在阳极和发光层之间具有空穴注入输送层以及在阴极和发光层之间具有电子注入输送层而成。
9.如权利要求8所述的有机电致发光元件，其在发光层和电子注入输送层之间具有空穴阻挡层而成。
CN201210072915.4A 2005-12-01 2006-11-22 有机电致发光元件用化合物及有机电致发光元件 Active CN102633820B (zh)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2005-347990 2005-12-01
JP2005347990 2005-12-01
JP2006278619 2006-10-12
JP2006-278619 2006-10-12
JP2006288568 2006-10-24
JP2006-288568 2006-10-24

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CN200680045030.8A Division CN101321755B (zh) 2005-12-01 2006-11-22 有机电致发光元件用化合物及有机电致发光元件

Publications (2)

Publication Number Publication Date
CN102633820A CN102633820A (zh) 2012-08-15
CN102633820B true CN102633820B (zh) 2015-01-21

Family

ID=38092089

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201210072915.4A Active CN102633820B (zh) 2005-12-01 2006-11-22 有机电致发光元件用化合物及有机电致发光元件
CN200680045030.8A Active CN101321755B (zh) 2005-12-01 2006-11-22 有机电致发光元件用化合物及有机电致发光元件

Family Applications After (1)

Application Number Title Priority Date Filing Date
CN200680045030.8A Active CN101321755B (zh) 2005-12-01 2006-11-22 有机电致发光元件用化合物及有机电致发光元件

Country Status (7)

Country Link
US (1) US7993760B2 (zh)
EP (1) EP1956022B1 (zh)
JP (1) JP4593631B2 (zh)
KR (1) KR101082258B1 (zh)
CN (2) CN102633820B (zh)
TW (1) TW200734340A (zh)
WO (1) WO2007063754A1 (zh)

Families Citing this family (1108)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9070884B2 (en) 2005-04-13 2015-06-30 Universal Display Corporation Hybrid OLED having phosphorescent and fluorescent emitters
US8586204B2 (en) 2007-12-28 2013-11-19 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
CN102633820B (zh) 2005-12-01 2015-01-21 新日铁住金化学株式会社 有机电致发光元件用化合物及有机电致发光元件
KR20160030330A (ko) 2006-02-10 2016-03-16 유니버셜 디스플레이 코포레이션 시클로금속화 이미다조[1,2-ｆ]페난트리딘 및 디이미다조[1,2-ａ:1'',2''-ｃ]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체
WO2008056746A1 (fr) * 2006-11-09 2008-05-15 Nippon Steel Chemical Co., Ltd. Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique
JP5187493B2 (ja) * 2006-11-27 2013-04-24 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子および新規なインドール誘導体
JP2009076834A (ja) * 2006-11-27 2009-04-09 Fujifilm Corp 有機電界発光素子および新規なインドール誘導体
US8778508B2 (en) 2006-12-08 2014-07-15 Universal Display Corporation Light-emitting organometallic complexes
KR101118808B1 (ko) 2006-12-28 2012-03-22 유니버셜 디스플레이 코포레이션 긴 수명의 인광 유기 발광 소자(ｏｌｅｄ) 구조체
US20130032785A1 (en) 2011-08-01 2013-02-07 Universal Display Corporation Materials for organic light emitting diode
US9130177B2 (en) 2011-01-13 2015-09-08 Universal Display Corporation 5-substituted 2 phenylquinoline complexes materials for light emitting diode
CN103087109B (zh) 2007-03-08 2015-10-28 通用显示公司 磷光材料
EP2138486B2 (en) * 2007-03-26 2022-10-19 NIPPON STEEL Chemical & Material Co., Ltd. Organic electroluminescent device
EP2141152B1 (en) * 2007-03-27 2021-05-05 NIPPON STEEL Chemical & Material Co., Ltd. Compound for organic electroluminescent device and organic electroluminescent device
TWI468489B (zh) * 2007-05-29 2015-01-11 Nippon Steel & Sumikin Chem Co Organic electroluminescent element compounds and organic electroluminescent elements
JP4519946B2 (ja) * 2007-05-30 2010-08-04 新日鐵化学株式会社 有機電界発光素子用化合物及び有機電界発光素子
EP3424918A1 (en) 2007-08-08 2019-01-09 Universal Display Corporation Single triphenylene chromophores in phosphorescent light emitting diodes
TWI511964B (zh) 2007-08-08 2015-12-11 Universal Display Corp 苯并稠合噻吩／聯伸三苯混合材料
WO2009085344A2 (en) 2007-12-28 2009-07-09 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
US8040053B2 (en) 2008-02-09 2011-10-18 Universal Display Corporation Organic light emitting device architecture for reducing the number of organic materials
DE102008013691A1 (de) 2008-03-11 2009-09-17 Merck Patent Gmbh Verwendung von Zusammensetzungen neutraler Übergangsmetallkomplexe in opto-elektronischen Bauelementen
TWI472074B (zh) * 2008-03-17 2015-02-01 Nippon Steel & Sumikin Chem Co Organic electroluminescent elements
EP2284920B1 (en) * 2008-05-08 2015-07-29 Nippon Steel & Sumikin Chemical Co., Ltd. Compound for organic electric field light-emitting element and organic electric field light-emitting element
CN102017221B (zh) * 2008-05-08 2013-01-02 新日铁化学株式会社 有机场致发光元件用化合物及有机场致发光元件
US8703303B2 (en) * 2008-05-08 2014-04-22 Nippon Steel & Sumikin Chemical Co., Ltd. Organic electroluminescent device having a light-emitting layer comprising a host material of two or more compounds
CN102056929A (zh) 2008-06-05 2011-05-11 出光兴产株式会社 卤素化合物、多环系化合物及使用其的有机电致发光元件
US8318323B2 (en) * 2008-06-05 2012-11-27 Idemitsu Kosan Co., Ltd. Polycyclic compounds and organic electroluminescence device employing the same
US8057919B2 (en) 2008-06-05 2011-11-15 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
EP2301921A4 (en) 2008-06-05 2012-06-20 Idemitsu Kosan Co POLYCYCLIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THIS
DE102008027005A1 (de) 2008-06-05 2009-12-10 Merck Patent Gmbh Organische elektronische Vorrichtung enthaltend Metallkomplexe
CN102056911B (zh) * 2008-06-05 2015-07-22 出光兴产株式会社 卤素化合物、多环系化合物及使用其的有机电致发光元件
US8049411B2 (en) 2008-06-05 2011-11-01 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
DE102008033563A1 (de) 2008-07-17 2010-01-21 Merck Patent Gmbh Komplexe mit kleinen Singulett-Triplett-Energie-Abständen zur Verwendung in opto-elektronischen Bauteilen (Singulett-Harvesting-Effekt)
DE102008036247A1 (de) * 2008-08-04 2010-02-11 Merck Patent Gmbh Elektronische Vorrichtungen enthaltend Metallkomplexe
WO2010027583A1 (en) 2008-09-03 2010-03-11 Universal Display Corporation Phosphorescent materials
US8513658B2 (en) 2008-09-04 2013-08-20 Universal Display Corporation White phosphorescent organic light emitting devices
TWI555734B (zh) 2008-09-16 2016-11-01 環球展覽公司 磷光物質
DE102008048336A1 (de) 2008-09-22 2010-03-25 Merck Patent Gmbh Einkernige neutrale Kupfer(I)-Komplexe und deren Verwendung zur Herstellung von optoelektronischen Bauelementen
KR101678235B1 (ko) 2008-09-25 2016-11-21 유니버셜 디스플레이 코포레이션 유기 셀레늄 재료들 및 유기 발광 소자들에서 이들의 사용
DE102008050841B4 (de) 2008-10-08 2019-08-01 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
US8053770B2 (en) 2008-10-14 2011-11-08 Universal Display Corporation Emissive layer patterning for OLED
DE102009022858A1 (de) 2009-05-27 2011-12-15 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
US8865321B2 (en) 2008-11-11 2014-10-21 Merck Patent Gmbh Organic electroluminescent devices
DE102008057050B4 (de) 2008-11-13 2021-06-02 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
US8778511B2 (en) 2008-12-12 2014-07-15 Universal Display Corporation OLED stability via doped hole transport layer
US8815415B2 (en) 2008-12-12 2014-08-26 Universal Display Corporation Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes
DE102008063490B4 (de) 2008-12-17 2023-06-15 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung und Verfahren zum Einstellen des Farbortes einer weiß emittierenden Elektrolumineszenzvorrichtung
DE102008064200A1 (de) * 2008-12-22 2010-07-01 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
US9067947B2 (en) 2009-01-16 2015-06-30 Universal Display Corporation Organic electroluminescent materials and devices
DE102009007038A1 (de) 2009-02-02 2010-08-05 Merck Patent Gmbh Metallkomplexe
DE102009009277B4 (de) 2009-02-17 2023-12-07 Merck Patent Gmbh Organische elektronische Vorrichtung, Verfahren zu deren Herstellung und Verwendung von Verbindungen
US8759818B2 (en) 2009-02-27 2014-06-24 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
US8795852B2 (en) 2009-02-27 2014-08-05 Nippon Steel & Sumikin Chemical Co., Ltd. Organic electroluminescent device with host materials having same or similar IP, EA and T1 values
DE102009011223A1 (de) 2009-03-02 2010-09-23 Merck Patent Gmbh Metallkomplexe
DE102009012346B4 (de) 2009-03-09 2024-02-15 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung und Verfahren zu deren Herstellung
DE102009013041A1 (de) 2009-03-13 2010-09-16 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
KR101511072B1 (ko) * 2009-03-20 2015-04-10 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자
US8709615B2 (en) 2011-07-28 2014-04-29 Universal Display Corporation Heteroleptic iridium complexes as dopants
US8722205B2 (en) 2009-03-23 2014-05-13 Universal Display Corporation Heteroleptic iridium complex
US11910700B2 (en) 2009-03-23 2024-02-20 Universal Display Corporation Heteroleptic iridium complexes as dopants
KR101477613B1 (ko) * 2009-03-31 2014-12-30 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전자 소자
TWI471405B (zh) * 2009-03-31 2015-02-01 Nippon Steel & Sumikin Chem Co A phosphorescent element material, and an organic electroluminescent device using the same
WO2010113761A1 (ja) * 2009-03-31 2010-10-07 新日鐵化学株式会社 有機電界発光素子
EP2414481A4 (en) 2009-04-03 2013-02-20 Du Pont ELECTROACTIVE MATERIALS
US9359549B2 (en) 2009-04-06 2016-06-07 Universal Display Corporation Organic electroluminescent materials and devices
DE102009017064A1 (de) 2009-04-09 2010-10-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
TWI770731B (zh) 2009-04-28 2022-07-11 美商環球展覽公司 具有甲基-d3取代之銥錯合物
TWI541234B (zh) 2009-05-12 2016-07-11 環球展覽公司 用於有機發光二極體之２－氮雜聯伸三苯材料
US8586203B2 (en) 2009-05-20 2013-11-19 Universal Display Corporation Metal complexes with boron-nitrogen heterocycle containing ligands
DE102009023155A1 (de) * 2009-05-29 2010-12-02 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
EP2445976A2 (en) 2009-06-22 2012-05-02 Merck Patent GmbH Conducting formulation
KR101174088B1 (ko) * 2009-06-25 2012-08-14 제일모직주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
DE102009031021A1 (de) 2009-06-30 2011-01-05 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009032922B4 (de) 2009-07-14 2024-04-25 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen, Verfahren zu deren Herstellung, deren Verwendung sowie elektronische Vorrichtung
EP2818462B1 (en) * 2009-08-21 2017-11-08 Tosoh Corporation Cyclic azine derivatives, processes for producing these, and organic electrolumiscent element containing these as component
JP5457907B2 (ja) * 2009-08-31 2014-04-02 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子
JP4564584B1 (ja) * 2009-08-31 2010-10-20 富士フイルム株式会社 有機電界発光素子
DE102009041289A1 (de) 2009-09-16 2011-03-17 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102009053644B4 (de) 2009-11-17 2019-07-04 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009053645A1 (de) 2009-11-17 2011-05-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtung
DE102009041414A1 (de) 2009-09-16 2011-03-17 Merck Patent Gmbh Metallkomplexe
DE102009042693A1 (de) 2009-09-23 2011-03-24 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
US8431245B2 (en) 2009-09-29 2013-04-30 E. I. Du Pont De Nemours And Company Deuterated compounds for luminescent applications
DE102009048791A1 (de) 2009-10-08 2011-04-14 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009049587A1 (de) 2009-10-16 2011-04-21 Merck Patent Gmbh Metallkomplexe
EP2493887A4 (en) * 2009-10-29 2013-06-19 Du Pont DETERERATED COMPOUNDS FOR ELECTRONIC APPLICATIONS
KR101212670B1 (ko) * 2009-11-03 2012-12-14 제일모직주식회사 유기광전소자용 조성물, 이를 이용한 유기광전소자 및 이를 포함하는 표시장치
DE102009053382A1 (de) 2009-11-14 2011-05-19 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102009053836A1 (de) 2009-11-18 2011-05-26 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
US8580394B2 (en) 2009-11-19 2013-11-12 Universal Display Corporation 3-coordinate copper(I)-carbene complexes
DE102009057167A1 (de) 2009-12-05 2011-06-09 Merck Patent Gmbh Elektronische Vorrichtung enthaltend Metallkomplexe
CN102648268B (zh) * 2009-12-07 2014-08-13 新日铁住金化学株式会社 有机发光材料及有机发光元件
KR101219492B1 (ko) * 2009-12-11 2013-01-28 삼성디스플레이 주식회사 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말
WO2011076323A1 (en) 2009-12-22 2011-06-30 Merck Patent Gmbh Formulations comprising phase-separated functional materials
EP2517278B1 (en) 2009-12-22 2019-07-17 Merck Patent GmbH Electroluminescent formulations
EP2517537B1 (en) 2009-12-22 2019-04-03 Merck Patent GmbH Electroluminescent functional surfactants
US9178156B2 (en) 2009-12-23 2015-11-03 Merck Patent Gmbh Compositions comprising polymeric binders
KR20170093267A (ko) 2009-12-23 2017-08-14 메르크 파텐트 게엠베하 유기 반도성 화합물을 포함하는 조성물
WO2011080972A1 (ja) * 2009-12-28 2011-07-07 新日鐵化学株式会社 有機電界発光素子
DE102010004803A1 (de) 2010-01-16 2011-07-21 Merck Patent GmbH, 64293 Materialien für organische Elektrolumineszenzvorrichtungen
US8288187B2 (en) 2010-01-20 2012-10-16 Universal Display Corporation Electroluminescent devices for lighting applications
DE102010005697A1 (de) 2010-01-25 2011-07-28 Merck Patent GmbH, 64293 Verbindungen für elektronische Vorrichtungen
TWI429650B (zh) 2010-02-12 2014-03-11 Nippon Steel & Sumikin Chem Co Organic electroluminescent elements
DE102010009193B4 (de) 2010-02-24 2022-05-19 MERCK Patent Gesellschaft mit beschränkter Haftung Zusammensetzung enthaltend Fluor-Fluor Assoziate, Verfahren zu deren Herstellung, deren Verwendung sowie organische elektronische Vorrichtung diese enthaltend
US9156870B2 (en) 2010-02-25 2015-10-13 Universal Display Corporation Phosphorescent emitters
DE102010009903A1 (de) 2010-03-02 2011-09-08 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
US9175211B2 (en) 2010-03-03 2015-11-03 Universal Display Corporation Phosphorescent materials
DE102010010481A1 (de) 2010-03-06 2011-09-08 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
JP2013522816A (ja) 2010-03-11 2013-06-13 メルク パテント ゲーエムベーハー 発光ファイバー
KR20130020883A (ko) 2010-03-11 2013-03-04 메르크 파텐트 게엠베하 요법 및 미용에서의 섬유
JP5577122B2 (ja) * 2010-03-18 2014-08-20 新日鉄住金化学株式会社 有機電界発光素子
US9627632B2 (en) 2010-03-23 2017-04-18 Merck Patent Gmbh Materials for organic electroluminescent devices
DE102010012738A1 (de) 2010-03-25 2011-09-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
KR101910331B1 (ko) 2010-03-25 2018-10-19 유니버셜 디스플레이 코포레이션 용액 처리 가능한 도핑된 트리아릴아민 정공 주입 물질
DE102010013068A1 (de) 2010-03-26 2011-09-29 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
EP2371828B1 (en) 2010-04-01 2018-01-10 Samsung Display Co., Ltd. Condensed-Cyclic Compound and Organic Light-Emitting Device Including the Same
CN102933582A (zh) * 2010-04-06 2013-02-13 巴斯夫欧洲公司 取代的咔唑衍生物及其在有机电子器件中的用途
KR101896723B1 (ko) 2010-04-12 2018-09-07 메르크 파텐트 게엠베하 유기 전자 소자 제조용 조성물 및 방법
WO2011128034A1 (en) 2010-04-12 2011-10-20 Merck Patent Gmbh Composition having improved performance
DE102010014933A1 (de) 2010-04-14 2011-10-20 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
WO2011132684A1 (ja) 2010-04-20 2011-10-27 出光興産株式会社 ビスカルバゾール誘導体、有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
DE102010018321A1 (de) 2010-04-27 2011-10-27 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
EP2564438B1 (en) 2010-04-28 2016-10-19 Universal Display Corporation Depositing premixed materials
US8968887B2 (en) 2010-04-28 2015-03-03 Universal Display Corporation Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
DE102010019306B4 (de) 2010-05-04 2021-05-20 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
DE102010020044A1 (de) 2010-05-11 2011-11-17 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102010020567A1 (de) 2010-05-14 2011-11-17 Merck Patent Gmbh Metallkomplexe
JPWO2011148909A1 (ja) * 2010-05-24 2013-07-25 出光興産株式会社 有機エレクトロルミネッセンス素子
KR101251453B1 (ko) * 2010-05-26 2013-04-05 덕산하이메탈(주) 헤테로 원자를 포함하는 카바졸과 플루오렌이 융합된 화합물 및 이를 이용한 유기전기소자, 그 단말
EP2576723B1 (en) 2010-05-27 2017-09-20 Merck Patent GmbH Compositions comprising quantum dots
US9206352B2 (en) 2010-05-27 2015-12-08 Merck Patent Gmbh Formulation and method for preparation of organic electronic devices
US8673458B2 (en) 2010-06-11 2014-03-18 Universal Display Corporation Delayed fluorescence OLED
US8742657B2 (en) 2010-06-11 2014-06-03 Universal Display Corporation Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications
WO2011157339A1 (de) 2010-06-15 2011-12-22 Merck Patent Gmbh Metallkomplexe
DE102010024335A1 (de) 2010-06-18 2011-12-22 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
DE102010024542A1 (de) 2010-06-22 2011-12-22 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102010024897A1 (de) 2010-06-24 2011-12-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010027218A1 (de) 2010-07-15 2012-01-19 Merck Patent Gmbh Organische Komplexe enthaltend Metalle
DE102010027319A1 (de) 2010-07-16 2012-01-19 Merck Patent Gmbh Metallkomplexe
DE102010027316A1 (de) 2010-07-16 2012-01-19 Merck Patent Gmbh Metallkomplexe
DE102010027317A1 (de) 2010-07-16 2012-01-19 Merck Patent Gmbh Metallkomplexe
EP2599141B1 (en) 2010-07-26 2019-12-11 Merck Patent GmbH Quantum dots and hosts
CN103026525B (zh) 2010-07-26 2016-11-09 默克专利有限公司 在器件中的纳米晶体
US9435021B2 (en) 2010-07-29 2016-09-06 University Of Southern California Co-deposition methods for the fabrication of organic optoelectronic devices
US9236578B2 (en) 2010-07-30 2016-01-12 Merck Patent Gmbh Organic electroluminescent device
DE102010033548A1 (de) 2010-08-05 2012-02-09 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
KR101753172B1 (ko) 2010-08-20 2017-07-04 유니버셜 디스플레이 코포레이션 Ｏｌｅｄ를 위한 바이카르바졸 화합물
CN102372718B (zh) * 2010-08-20 2014-12-17 清华大学 一种含有吡啶基团的并咔唑类化合物及其应用
JP2012056880A (ja) * 2010-09-08 2012-03-22 Idemitsu Kosan Co Ltd インドロカルバゾール化合物、有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子
DE102010045405A1 (de) 2010-09-15 2012-03-15 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010046412B4 (de) 2010-09-23 2022-01-13 Merck Patent Gmbh Metall-Ligand Koordinationsverbindungen
DE102010046512A1 (de) 2010-09-24 2012-03-29 Merck Patent Gmbh Phosphorhaltige Metallkomplexe
US8932734B2 (en) 2010-10-08 2015-01-13 Universal Display Corporation Organic electroluminescent materials and devices
DE102010048074A1 (de) 2010-10-09 2012-04-12 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102010048608A1 (de) 2010-10-15 2012-04-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010048607A1 (de) 2010-10-15 2012-04-19 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
CN103228647B (zh) 2010-11-24 2017-02-15 默克专利有限公司 用于有机电致发光器件的材料
CN103229324B (zh) * 2010-11-25 2016-08-10 新日铁住金化学株式会社 有机电致发光元件
US20120138906A1 (en) 2010-12-07 2012-06-07 The University of Southern California USC Stevens Institute for Innovation Capture agents for unsaturated metal complexes
DE102010054316A1 (de) 2010-12-13 2012-06-14 Merck Patent Gmbh Substituierte Tetraarylbenzole
DE102010054525A1 (de) 2010-12-15 2012-04-26 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102011106849A1 (de) 2010-12-15 2012-06-21 Merck Patent Gmbh Verfahren zur Synthese N-N verknüpfter und um die N-N Bindung rotationsgehinderter bis-N-heterocyclische Carbene und deren Einsatz als Liganden für Metallkomplexe
WO2012087955A1 (en) 2010-12-20 2012-06-28 E. I. Du Pont De Nemours And Company Compositions for electronic applications
DE102010055902A1 (de) 2010-12-23 2012-06-28 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102010055901A1 (de) 2010-12-23 2012-06-28 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
JP5756288B2 (ja) * 2010-12-28 2015-07-29 出光興産株式会社 縮合多環化合物、有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子
JP2012140367A (ja) * 2010-12-28 2012-07-26 Idemitsu Kosan Co Ltd 縮合多環化合物、有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子
EP2663567B1 (de) 2011-01-13 2016-06-01 Merck Patent GmbH Verbindungen für organische elektrolumineszenzvorrichtungen
US10008677B2 (en) 2011-01-13 2018-06-26 Universal Display Corporation Materials for organic light emitting diode
DE102012000064A1 (de) 2011-01-21 2012-07-26 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
US8751777B2 (en) 2011-01-28 2014-06-10 Honeywell International Inc. Methods and reconfigurable systems to optimize the performance of a condition based health maintenance system
DE102011010841A1 (de) 2011-02-10 2012-08-16 Merck Patent Gmbh (1,3)-Dioxan-5-on-Verbindungen
DE102011011104A1 (de) 2011-02-12 2012-08-16 Merck Patent Gmbh Substituierte Dibenzonaphtacene
US9492681B2 (en) 2011-02-14 2016-11-15 Merck Patent Gmbh Device and method for treatment of cells and cell tissue
DE112012000831C5 (de) 2011-02-16 2022-06-15 Semiconductor Energy Laboratory Co., Ltd. Licht emittierendes Element
WO2012111579A1 (en) 2011-02-16 2012-08-23 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element
DE102011011539A1 (de) 2011-02-17 2012-08-23 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
US9564600B2 (en) 2011-02-22 2017-02-07 Hodogaya Chemical Co., Ltd. Compound having an indolocarbazole ring structure and organic electroluminescent device
US8563737B2 (en) 2011-02-23 2013-10-22 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
TW201841932A (zh) 2011-02-23 2018-12-01 美商環球展覽公司 新穎四牙鉑錯合物
US9005772B2 (en) 2011-02-23 2015-04-14 Universal Display Corporation Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials
TWI743606B (zh) 2011-02-28 2021-10-21 日商半導體能源研究所股份有限公司 發光元件
US8883322B2 (en) 2011-03-08 2014-11-11 Universal Display Corporation Pyridyl carbene phosphorescent emitters
CN103430344B (zh) 2011-03-14 2016-03-23 东丽株式会社 发光元件材料及发光元件
CN103582641B (zh) 2011-03-16 2016-05-04 新日铁住金化学株式会社 含氮芳香族化合物和有机场致发光元件
KR102333528B1 (ko) 2011-03-23 2021-12-01 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자
EP2688646A1 (en) 2011-03-24 2014-01-29 Merck Patent GmbH Organic ionic functional materials
TWI552406B (zh) * 2011-03-25 2016-10-01 出光興產股份有限公司 有機電致發光元件
US9469667B2 (en) 2011-04-04 2016-10-18 Merck Patent Gmbh Metal complexes
CN103477462B (zh) 2011-04-05 2016-05-25 默克专利有限公司 有机电致发光器件
JP5922223B2 (ja) 2011-04-13 2016-05-24 メルク パテント ゲーエムベーハー 電子デバイス用化合物
EP2697225B1 (de) 2011-04-13 2015-10-07 Merck Patent GmbH Materialien für elektronische vorrichtungen
US9735371B2 (en) 2011-04-18 2017-08-15 Merck Patent Gmbh Compounds for electronic devices
JP6215192B2 (ja) 2011-04-18 2017-10-18 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子用材料
WO2012149992A1 (de) 2011-05-04 2012-11-08 Merck Patent Gmbh Vorrichtung zur aufbewahrung von frischwaren
US10177312B2 (en) 2011-05-05 2019-01-08 Merck Patent Gmbh Compounds for electronic devices
JP6193215B2 (ja) 2011-05-05 2017-09-06 メルク パテント ゲーエムベーハー 電子デバイスのための化合物
US8927308B2 (en) 2011-05-12 2015-01-06 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
US8432095B2 (en) 2011-05-11 2013-04-30 Universal Display Corporation Process for fabricating metal bus lines for OLED lighting panels
KR101971895B1 (ko) 2011-05-12 2019-04-25 도레이 카부시키가이샤 발광 소자 재료 및 발광 소자
US9496502B2 (en) 2011-05-12 2016-11-15 Merck Patent Gmbh Organic ionic compounds, compositions and electronic devices
DE102012007810A1 (de) 2011-05-16 2012-11-22 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
US9212197B2 (en) 2011-05-19 2015-12-15 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants
US8795850B2 (en) 2011-05-19 2014-08-05 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology
US10079349B2 (en) 2011-05-27 2018-09-18 Universal Display Corporation Organic electroluminescent materials and devices
DE102011102586A1 (de) 2011-05-27 2012-11-29 Merck Patent Gmbh Organische elektronische Vorrichtung
US10158089B2 (en) 2011-05-27 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
KR101934135B1 (ko) 2011-06-03 2019-04-05 메르크 파텐트 게엠베하 유기 전계발광 디바이스
JP6125492B2 (ja) 2011-06-03 2017-05-10 メルク パテント ゲーエムベーハー 金属錯体
WO2012170571A1 (en) 2011-06-08 2012-12-13 Universal Display Corporation Heteroleptic iridium carbene complexes and light emitting device using them
US8659036B2 (en) 2011-06-17 2014-02-25 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
US8884316B2 (en) 2011-06-17 2014-11-11 Universal Display Corporation Non-common capping layer on an organic device
WO2013002053A1 (ja) * 2011-06-27 2013-01-03 新日鉄住金化学株式会社 有機電界発光素子用重合体及びそれを用いた有機電界発光素子
EP2726490B1 (de) 2011-06-28 2015-04-29 Merck Patent GmbH Metallkomplexe
US9397310B2 (en) 2011-07-14 2016-07-19 Universal Display Corporation Organice electroluminescent materials and devices
KR101965014B1 (ko) 2011-07-14 2019-04-02 유니버셜 디스플레이 코포레이션 Ｏｌｅｄ에서 무기 호스트
US9023420B2 (en) 2011-07-14 2015-05-05 Universal Display Corporation Composite organic/inorganic layer for organic light-emitting devices
US9783564B2 (en) 2011-07-25 2017-10-10 Universal Display Corporation Organic electroluminescent materials and devices
WO2013017189A1 (de) 2011-07-29 2013-02-07 Merck Patent Gmbh Verbindungen für elektronische vorrichtungen
CN103718317B (zh) 2011-08-03 2016-11-16 默克专利有限公司 用于电子器件的材料
US8926119B2 (en) 2011-08-04 2015-01-06 Universal Display Corporation Extendable light source with variable light emitting area
EP2742054B1 (de) 2011-08-10 2016-10-12 Merck Patent GmbH Metallkomplexe
DE102012016192A1 (de) 2011-08-19 2013-02-21 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
KR101914951B1 (ko) 2011-08-22 2018-11-05 메르크 파텐트 게엠베하 유기 전계발광 디바이스
US9493698B2 (en) 2011-08-31 2016-11-15 Universal Display Corporation Organic electroluminescent materials and devices
KR102077994B1 (ko) 2011-09-21 2020-02-17 메르크 파텐트 게엠베하 유기 전계발광 소자용 카르바졸 유도체
DE102011116165A1 (de) 2011-10-14 2013-04-18 Merck Patent Gmbh Benzodioxepin-3-on-Verbindungen
WO2013056776A1 (de) 2011-10-20 2013-04-25 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
US10128456B2 (en) 2011-10-26 2018-11-13 Idemitsu Kosan Co., Ltd. Organic electroluminescence element, and material for organic electroluminescence element
JP6223984B2 (ja) 2011-10-27 2017-11-01 メルク パテント ゲーエムベーハー 電子素子のための材料
DE102011117422A1 (de) 2011-10-28 2013-05-02 Merck Patent Gmbh Hyperverzweigte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung in elektronischen Vorrichtungen
KR102021162B1 (ko) 2011-11-01 2019-09-11 메르크 파텐트 게엠베하 유기 전계발광 소자
US8652656B2 (en) 2011-11-14 2014-02-18 Universal Display Corporation Triphenylene silane hosts
US9193745B2 (en) 2011-11-15 2015-11-24 Universal Display Corporation Heteroleptic iridium complex
KR102310368B1 (ko) 2011-11-17 2021-10-07 메르크 파텐트 게엠베하 스피로디히드로아크리딘 유도체 및 이의 유기 전계발광 소자용 재료로서의 용도
US9217004B2 (en) 2011-11-21 2015-12-22 Universal Display Corporation Organic light emitting materials
US9512355B2 (en) 2011-12-09 2016-12-06 Universal Display Corporation Organic light emitting materials
CN105742499B (zh) 2011-12-12 2018-02-13 默克专利有限公司 用于电子器件的化合物
US20130146875A1 (en) 2011-12-13 2013-06-13 Universal Display Corporation Split electrode for organic devices
DE102012022880A1 (de) 2011-12-22 2013-06-27 Merck Patent Gmbh Elektronische Vorrichtungen enthaltend organische Schichten
KR101497133B1 (ko) 2011-12-23 2015-02-27 제일모직 주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
JP2015504884A (ja) 2011-12-27 2015-02-16 メルク パテント ゲーエムベーハー １，２，３−トリアゾールを含む金属錯体
US8987451B2 (en) 2012-01-03 2015-03-24 Universal Display Corporation Synthesis of cyclometallated platinum(II) complexes
US9461254B2 (en) 2012-01-03 2016-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US9163174B2 (en) 2012-01-04 2015-10-20 Universal Display Corporation Highly efficient phosphorescent materials
KR102012047B1 (ko) 2012-01-06 2019-08-19 유니버셜 디스플레이 코포레이션 효율이 큰 인광 물질
US8969592B2 (en) 2012-01-10 2015-03-03 Universal Display Corporation Heterocyclic host materials
US9748502B2 (en) 2012-01-16 2017-08-29 Merck Patent Gmbh Organic metal complexes
US10211413B2 (en) 2012-01-17 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
KR101498278B1 (ko) 2012-01-18 2015-03-06 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치
WO2013113349A1 (en) 2012-01-30 2013-08-08 Merck Patent Gmbh Nanocrystals on fibers
KR101803537B1 (ko) * 2012-02-09 2017-11-30 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자
KR101605987B1 (ko) 2012-02-14 2016-03-23 메르크 파텐트 게엠베하 유기 전계발광 소자용 스피로비플루오렌 화합물
US9118017B2 (en) 2012-02-27 2015-08-25 Universal Display Corporation Host compounds for red phosphorescent OLEDs
KR102044720B1 (ko) * 2012-03-05 2019-11-14 도레이 카부시키가이샤 발광 소자
CN107254306B (zh) 2012-03-14 2020-08-25 株式会社半导体能源研究所 发光元件、发光装置、电子设备及照明装置
KR102268695B1 (ko) 2012-03-15 2021-06-23 메르크 파텐트 게엠베하 전자 소자
US9386657B2 (en) 2012-03-15 2016-07-05 Universal Display Corporation Organic Electroluminescent materials and devices
US9054323B2 (en) 2012-03-15 2015-06-09 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
CN104203955B (zh) 2012-03-23 2017-11-17 默克专利有限公司 用于电致发光器件的9,9，‑螺二氧杂蒽衍生物
KR101973166B1 (ko) 2012-03-27 2019-04-29 삼성디스플레이 주식회사 유기 발광 소자 및 이를 포함하는 유기 발광 표시 장치
TWI585091B (zh) * 2012-03-30 2017-06-01 新日鐵住金化學股份有限公司 Organic electroluminescent elements
JP2013232629A (ja) 2012-04-06 2013-11-14 Semiconductor Energy Lab Co Ltd 発光素子、発光装置、電子機器、および照明装置
JP6158542B2 (ja) 2012-04-13 2017-07-05 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器、および照明装置
JP6076153B2 (ja) 2012-04-20 2017-02-08 株式会社半導体エネルギー研究所 発光素子、発光装置、表示装置、電子機器及び照明装置
KR20240129241A (ko) 2012-04-20 2024-08-27 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
US9184399B2 (en) 2012-05-04 2015-11-10 Universal Display Corporation Asymmetric hosts with triaryl silane side chains
US9773985B2 (en) 2012-05-21 2017-09-26 Universal Display Corporation Organic electroluminescent materials and devices
US9879177B2 (en) 2012-05-24 2018-01-30 Merck Patent Gmbh Metal complexes comprising condensed heteroaromatic rings
DE102012011335A1 (de) 2012-06-06 2013-12-12 Merck Patent Gmbh Verbindungen für Organische Elekronische Vorrichtungen
US9670404B2 (en) 2012-06-06 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
CN102738413B (zh) * 2012-06-15 2016-08-03 固安翌光科技有限公司 一种有机电致发光器件及其制备方法
US9502672B2 (en) 2012-06-21 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
KR101423375B1 (ko) * 2012-06-27 2014-07-28 (주) 에프엔지리서치 유기전계발광 소자 제조용 테트라키스 페닐계 유기화합물
US9725476B2 (en) 2012-07-09 2017-08-08 Universal Display Corporation Silylated metal complexes
US9231218B2 (en) 2012-07-10 2016-01-05 Universal Display Corporation Phosphorescent emitters containing dibenzo[1,4]azaborinine structure
EP2872589B1 (de) 2012-07-10 2017-07-26 Merck Patent GmbH Materialien für organische elektrolumineszenzvorrichtungen
JP2015529637A (ja) 2012-07-13 2015-10-08 メルク パテント ゲーエムベーハー 金属錯体
KR101401620B1 (ko) * 2012-07-17 2014-06-02 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
US9540329B2 (en) 2012-07-19 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9059412B2 (en) 2012-07-19 2015-06-16 Universal Display Corporation Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs
KR101452577B1 (ko) * 2012-07-20 2014-10-21 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102125199B1 (ko) 2012-07-23 2020-06-22 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
KR102337198B1 (ko) 2012-07-23 2021-12-09 메르크 파텐트 게엠베하 화합물 및 유기 전계 발광 디바이스
KR101452578B1 (ko) 2012-07-23 2014-10-23 주식회사 두산 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
DE202013012401U1 (de) 2012-07-23 2016-10-12 Merck Patent Gmbh Verbindungen und Organische Elektronische Vorrichtungen
US9768391B2 (en) 2012-07-23 2017-09-19 Merck Patent Gmbh Derivatives of 2-diarylaminofluorene and organic electronic compounds containing them
JP6299223B2 (ja) 2012-07-25 2018-03-28 東レ株式会社 発光素子材料および発光素子
US9663544B2 (en) 2012-07-25 2017-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US9318710B2 (en) 2012-07-30 2016-04-19 Universal Display Corporation Organic electroluminescent materials and devices
TWI666299B (zh) 2012-08-03 2019-07-21 日商半導體能源研究所股份有限公司 發光元件
KR102137376B1 (ko) 2012-08-03 2020-07-24 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 전자 기기, 및 조명 장치
CN107068913B (zh) 2012-08-03 2019-04-30 株式会社半导体能源研究所 发光元件、发光装置、电子设备以及照明装置
TWI733065B (zh) 2012-08-03 2021-07-11 日商半導體能源研究所股份有限公司 發光元件、發光裝置、顯示裝置、電子裝置及照明設備
EP2882763B1 (de) 2012-08-07 2018-08-22 Merck Patent GmbH Metallkomplexe
US20150243897A1 (en) 2012-08-10 2015-08-27 Merck Patent Gmbh Materials for organic electroluminescence devices
KR102204794B1 (ko) 2012-08-10 2021-01-18 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 전자 기기 및 조명 장치
EP2890221A4 (en) 2012-08-24 2016-09-14 Konica Minolta Inc TRANSPARENT ELECTRODE, ELECTRONIC DEVICE AND METHOD FOR PRODUCING THE TRANSPARENT ELECTRODE
US9978958B2 (en) 2012-08-24 2018-05-22 Universal Display Corporation Phosphorescent emitters with phenylimidazole ligands
US8952362B2 (en) 2012-08-31 2015-02-10 The Regents Of The University Of Michigan High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion
US10957870B2 (en) 2012-09-07 2021-03-23 Universal Display Corporation Organic light emitting device
EP2898042B1 (de) 2012-09-18 2016-07-06 Merck Patent GmbH Materialien für elektronische vorrichtungen
WO2014044347A1 (de) 2012-09-20 2014-03-27 Merck Patent Gmbh Metallkomplexe
US9287513B2 (en) 2012-09-24 2016-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US9312505B2 (en) 2012-09-25 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9252363B2 (en) 2012-10-04 2016-02-02 Universal Display Corporation Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers
EP2906661B1 (de) 2012-10-11 2016-10-26 Merck Patent GmbH Materialien für organische elektrolumineszenzvorrichtungen
DE102012020167A1 (de) 2012-10-13 2014-04-17 Eberhard Karls Universität Tübingen Metallkomplexe
JP6123679B2 (ja) * 2012-10-18 2017-05-10 東レ株式会社 ベンゾインドロカルバゾール誘導体、それを用いた発光素子材料および発光素子
EP3806176A1 (de) 2012-10-31 2021-04-14 Merck Patent GmbH Elektronische vorrichtung
DE102012021650A1 (de) 2012-11-03 2014-05-08 Eberhard Karls Universität Tübingen Metallkomplexe
US8692241B1 (en) 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands
US9685617B2 (en) 2012-11-09 2017-06-20 Universal Display Corporation Organic electronuminescent materials and devices
US8946697B1 (en) 2012-11-09 2015-02-03 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US9634264B2 (en) 2012-11-09 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US9748500B2 (en) 2015-01-15 2017-08-29 Universal Display Corporation Organic light emitting materials
WO2014072017A1 (de) 2012-11-12 2014-05-15 Merck Patent Gmbh Materialien für elektronische vorrichtungen
KR102105810B1 (ko) 2012-11-20 2020-04-29 메르크 파텐트 게엠베하 전자 장치 제조용 고순도 용매 중의 제형
US10069090B2 (en) 2012-11-20 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US9190623B2 (en) 2012-11-20 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9512136B2 (en) 2012-11-26 2016-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US9166175B2 (en) 2012-11-27 2015-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US10065959B2 (en) 2012-11-30 2018-09-04 Merck Patent Gmbh Electronic device
US9196860B2 (en) 2012-12-04 2015-11-24 Universal Display Corporation Compounds for triplet-triplet annihilation upconversion
US8716484B1 (en) 2012-12-05 2014-05-06 Universal Display Corporation Hole transporting materials with twisted aryl groups
US9209411B2 (en) 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US9653691B2 (en) 2012-12-12 2017-05-16 Universal Display Corporation Phosphorescence-sensitizing fluorescence material system
US20150329772A1 (en) 2013-01-03 2015-11-19 Merck Patent Gmbh Materials for Electronic Devices
EP2941469A2 (de) 2013-01-03 2015-11-11 Merck Patent GmbH Materialien für elektronische vorrichtungen
WO2014109274A1 (en) 2013-01-10 2014-07-17 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
US10400163B2 (en) 2013-02-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10367154B2 (en) 2013-02-21 2019-07-30 Universal Display Corporation Organic electroluminescent materials and devices
WO2014132922A1 (ja) 2013-02-28 2014-09-04 新日鉄住金化学株式会社 有機電界発光素子用ホウ素化合物及び有機電界発光素子
US8927749B2 (en) 2013-03-07 2015-01-06 Universal Display Corporation Organic electroluminescent materials and devices
US9419225B2 (en) 2013-03-14 2016-08-16 Universal Display Corporation Organic electroluminescent materials and devices
US9997712B2 (en) 2013-03-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
KR101798307B1 (ko) 2013-03-29 2017-11-15 코니카 미놀타 가부시키가이샤 유기 일렉트로루미네센스 소자용 재료, 유기 일렉트로루미네센스 소자, 표시 장치 및 조명 장치
WO2014157618A1 (ja) 2013-03-29 2014-10-02 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、それを具備した照明装置及び表示装置
KR20200133011A (ko) 2013-04-08 2020-11-25 메르크 파텐트 게엠베하 열 활성화 지연 형광 재료를 갖는 유기 전계발광 디바이스
CN105102581A (zh) * 2013-04-08 2015-11-25 默克专利有限公司 有机电致发光器件
US10193094B2 (en) 2013-04-08 2019-01-29 Merck Patent Gmbh Organic light-emitting device having delayed fluorescence
EP2984151B1 (de) 2013-04-08 2018-04-25 Merck Patent GmbH Organische elektrolumineszenzvorrichtung
US10043982B2 (en) 2013-04-26 2018-08-07 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, display device, electronic device, and lighting device
US9537106B2 (en) 2013-05-09 2017-01-03 Universal Display Corporation Organic electroluminescent materials and devices
DE102013008189A1 (de) 2013-05-14 2014-12-04 Eberhard Karls Universität Tübingen Metallkomplexe
KR102109485B1 (ko) * 2013-05-15 2020-05-12 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102198634B1 (ko) 2013-05-16 2021-01-06 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
US9735373B2 (en) 2013-06-10 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
KR102214317B1 (ko) 2013-06-14 2021-02-08 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 금속 이리듐 착체, 발광 소자, 발광 장치, 및 조명 장치
KR102691679B1 (ko) 2013-06-26 2024-08-05 이데미쓰 고산 가부시키가이샤 화합물, 유기 일렉트로 루미네선스 소자용 재료, 유기 일렉트로 루미네선스 소자, 및 전자 기기
US9673401B2 (en) 2013-06-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US10199581B2 (en) 2013-07-01 2019-02-05 Universal Display Corporation Organic electroluminescent materials and devices
WO2015000549A1 (de) * 2013-07-02 2015-01-08 Merck Patent Gmbh Materialien für elektronische vorrichtungen
US10121975B2 (en) 2013-07-03 2018-11-06 Universal Display Corporation Organic electroluminescent materials and devices
JP2016179943A (ja) 2013-07-11 2016-10-13 出光興産株式会社 化合物、及びそれを用いた有機エレクトロルミネッセンス素子
US9761807B2 (en) 2013-07-15 2017-09-12 Universal Display Corporation Organic light emitting diode materials
US9324949B2 (en) 2013-07-16 2016-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US9553274B2 (en) 2013-07-16 2017-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US9224958B2 (en) 2013-07-19 2015-12-29 Universal Display Corporation Organic electroluminescent materials and devices
US20150028290A1 (en) 2013-07-25 2015-01-29 Universal Display Corporation Heteroleptic osmium complex and method of making the same
EP3712229A1 (de) 2013-07-30 2020-09-23 Merck Patent GmbH Materialien für elektronische vorrichtungen
WO2015014434A1 (de) * 2013-07-30 2015-02-05 Merck Patent Gmbh Materialien für elektronische vorrichtungen
US9831437B2 (en) 2013-08-20 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US10074806B2 (en) 2013-08-20 2018-09-11 Universal Display Corporation Organic electroluminescent materials and devices
DE112014007321B3 (de) 2013-08-26 2022-01-20 Semiconductor Energy Laboratory Co., Ltd. Lichtemittierende Vorrichtung
US9932359B2 (en) 2013-08-30 2018-04-03 University Of Southern California Organic electroluminescent materials and devices
US10199582B2 (en) 2013-09-03 2019-02-05 University Of Southern California Organic electroluminescent materials and devices
US9735378B2 (en) 2013-09-09 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9748503B2 (en) 2013-09-13 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US10003034B2 (en) 2013-09-30 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
CN111848659A (zh) 2013-10-02 2020-10-30 默克专利有限公司 用于oled中的含硼化合物
US9831447B2 (en) 2013-10-08 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9293712B2 (en) 2013-10-11 2016-03-22 Universal Display Corporation Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same
US9853229B2 (en) 2013-10-23 2017-12-26 University Of Southern California Organic electroluminescent materials and devices
US20150115250A1 (en) 2013-10-29 2015-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US9306179B2 (en) 2013-11-08 2016-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US9647218B2 (en) 2013-11-14 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US10056565B2 (en) 2013-11-20 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
WO2015083021A1 (en) 2013-12-02 2015-06-11 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic appliance, and lighting device
KR102639622B1 (ko) 2013-12-02 2024-02-23 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 모듈, 조명 모듈, 발광 장치, 표시 장치, 전자 기기, 및 조명 장치
US10644251B2 (en) 2013-12-04 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
CN105980518B (zh) 2013-12-06 2019-07-12 默克专利有限公司 化合物和有机电子器件
WO2015082037A1 (en) 2013-12-06 2015-06-11 Merck Patent Gmbh Compositions containing a polymeric binder which comprises acrylic and/or methacrylic acid ester units
WO2015082046A2 (de) 2013-12-06 2015-06-11 Merck Patent Gmbh Substituierte oxepine
US9876173B2 (en) 2013-12-09 2018-01-23 Universal Display Corporation Organic electroluminescent materials and devices
JP6644688B2 (ja) 2013-12-12 2020-02-12 メルク パテント ゲーエムベーハー 電子素子のための材料
US10355227B2 (en) 2013-12-16 2019-07-16 Universal Display Corporation Metal complex for phosphorescent OLED
EP4438693A2 (de) 2013-12-19 2024-10-02 Merck Patent GmbH Heterocyclische spiroverbindungen
US9847496B2 (en) 2013-12-23 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10135008B2 (en) 2014-01-07 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US9978961B2 (en) 2014-01-08 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9755159B2 (en) 2014-01-23 2017-09-05 Universal Display Corporation Organic materials for OLEDs
US9935277B2 (en) 2014-01-30 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9590194B2 (en) 2014-02-14 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US10003033B2 (en) 2014-02-18 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9847497B2 (en) 2014-02-18 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10707423B2 (en) 2014-02-21 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US9647217B2 (en) 2014-02-24 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9502656B2 (en) 2014-02-24 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US10403825B2 (en) 2014-02-27 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US9673407B2 (en) 2014-02-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9181270B2 (en) 2014-02-28 2015-11-10 Universal Display Corporation Method of making sulfide compounds
US9590195B2 (en) 2014-02-28 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
KR20160132025A (ko) * 2014-03-12 2016-11-16 이데미쓰 고산 가부시키가이샤 조성물, 화합물, 유기 전기발광 소자용 재료, 잉크 조성물, 유기 전기발광 소자, 및 전자 기기
US9397309B2 (en) 2014-03-13 2016-07-19 Universal Display Corporation Organic electroluminescent devices
US10208026B2 (en) 2014-03-18 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US9748504B2 (en) 2014-03-25 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
EP2927300B1 (en) 2014-03-31 2016-11-16 Commonwealth Scientific and Industrial Research Organisation Phenylenediamine compounds for phosphorescent diazaborole metal complexes
EP2927221A1 (en) 2014-03-31 2015-10-07 Commonwealth Scientific and Industrial Research Organisation Diamine compounds for phosphorescent diazaborole metal complexes and electroluminescent devices
US9929353B2 (en) 2014-04-02 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9691993B2 (en) 2014-04-09 2017-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US10008679B2 (en) 2014-04-14 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US9847498B2 (en) 2014-04-14 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10256427B2 (en) 2014-04-15 2019-04-09 Universal Display Corporation Efficient organic electroluminescent devices
US9450198B2 (en) 2014-04-15 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US9741941B2 (en) 2014-04-29 2017-08-22 Universal Display Corporation Organic electroluminescent materials and devices
JP6789825B2 (ja) 2014-04-30 2020-11-25 メルク パテント ゲーエムベーハー 電子素子のための材料
US10457699B2 (en) 2014-05-02 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
KR101730779B1 (ko) 2014-05-05 2017-04-26 메르크 파텐트 게엠베하 유기 발광 소자용 재료
US10301338B2 (en) 2014-05-08 2019-05-28 Universal Display Corporation Organic electroluminescent materials and devices
EP3140871B1 (en) 2014-05-08 2018-12-26 Universal Display Corporation Stabilized imidazophenanthridine materials
US10636983B2 (en) 2014-05-08 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US10403830B2 (en) 2014-05-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
KR20150130224A (ko) 2014-05-13 2015-11-23 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 전자 기기, 및 조명 장치
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
TWI682563B (zh) 2014-05-30 2020-01-11 日商半導體能源研究所股份有限公司 發光元件，發光裝置，電子裝置以及照明裝置
US10461260B2 (en) 2014-06-03 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
DE102015006708A1 (de) 2014-06-12 2015-12-17 Merck Patent Gmbh Metallkomplexe
DE102014008722B4 (de) 2014-06-18 2024-08-22 Merck Patent Gmbh Zusammensetzungen für elektronische Vorrichtungen, Formulierung diese enthaltend, Verwendung der Zusammensetzung, Verwendung der Formulierung sowie organische elektronische Vorrichtung enthaltend die Zusammensetzung
JP6556764B2 (ja) 2014-06-25 2019-08-07 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
US9911931B2 (en) 2014-06-26 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
EP2960315A1 (de) 2014-06-27 2015-12-30 cynora GmbH Organische Elektrolumineszenzvorrichtung
EP2963044A1 (de) 2014-06-30 2016-01-06 cynora GmbH Zweikernige Metall(I)-Komplexe mit tetradentaten Liganden für optoelektronische Anwendungen
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10566546B2 (en) 2014-07-14 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
EP3172775B1 (de) 2014-07-21 2022-04-20 Merck Patent GmbH Materialien für elektronische vorrichtungen
US9929357B2 (en) 2014-07-22 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
JP6780925B2 (ja) 2014-07-25 2020-11-04 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器及び照明装置
US10411200B2 (en) 2014-08-07 2019-09-10 Universal Display Corporation Electroluminescent (2-phenylpyridine)iridium complexes and devices
US11108000B2 (en) 2014-08-07 2021-08-31 Unniversal Display Corporation Organic electroluminescent materials and devices
DE102014012818A1 (de) 2014-08-28 2016-03-03 Eberhard Karls Universität Tübingen Metallkomplexe
KR102353647B1 (ko) 2014-08-29 2022-01-20 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 및 조명 장치
JP6695863B2 (ja) 2014-09-05 2020-05-20 メルク パテント ゲーエムベーハー 調合物と電子素子
US10135007B2 (en) 2014-09-29 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
JP6383623B2 (ja) * 2014-09-29 2018-08-29 新日鉄住金化学株式会社 有機電界発光素子
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10043987B2 (en) 2014-09-29 2018-08-07 Universal Display Corporation Organic electroluminescent materials and devices
JP6378993B2 (ja) * 2014-09-29 2018-08-22 新日鉄住金化学株式会社 有機電界発光素子
WO2016051309A1 (en) 2014-09-30 2016-04-07 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display device, electronic device, and lighting device
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US9397302B2 (en) 2014-10-08 2016-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US10854826B2 (en) 2014-10-08 2020-12-01 Universal Display Corporation Organic electroluminescent compounds, compositions and devices
US10950803B2 (en) 2014-10-13 2021-03-16 Universal Display Corporation Compounds and uses in devices
US9484541B2 (en) 2014-10-20 2016-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US10868261B2 (en) 2014-11-10 2020-12-15 Universal Display Corporation Organic electroluminescent materials and devices
EP3218368B1 (de) 2014-11-11 2020-11-25 Merck Patent GmbH Materialien für organische elektrolumineszenzvorrichtungen
US10038151B2 (en) 2014-11-12 2018-07-31 Universal Display Corporation Organic electroluminescent materials and devices
US10411201B2 (en) 2014-11-12 2019-09-10 Universal Display Corporation Organic electroluminescent materials and devices
US9882151B2 (en) 2014-11-14 2018-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US9871212B2 (en) 2014-11-14 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
JP5930005B2 (ja) * 2014-11-17 2016-06-08 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子及びその製造方法、表示装置並びに照明装置
WO2016079097A1 (de) 2014-11-18 2016-05-26 Cynora Gmbh Kupfer(i)komplexe für optoelektronische anwendungen
US9761814B2 (en) 2014-11-18 2017-09-12 Universal Display Corporation Organic light-emitting materials and devices
US9444075B2 (en) 2014-11-26 2016-09-13 Universal Display Corporation Emissive display with photo-switchable polarization
CN107001334A (zh) 2014-12-12 2017-08-01 默克专利有限公司 具有可溶性基团的有机化合物
US9450195B2 (en) 2014-12-17 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US10636978B2 (en) 2014-12-30 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US10253252B2 (en) 2014-12-30 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
WO2016107663A1 (de) 2014-12-30 2016-07-07 Merck Patent Gmbh Formulierungen und elektronische vorrichtungen
US9312499B1 (en) 2015-01-05 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
KR20170102014A (ko) * 2015-01-13 2017-09-06 광저우 차이나레이 옵토일렉트로닉 머티리얼즈 엘티디. 화합물, 이를 포함하는 혼합물, 조성물 및 유기 전자 장치
US10418569B2 (en) 2015-01-25 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US9711730B2 (en) 2015-01-25 2017-07-18 Universal Display Corporation Organic electroluminescent materials and devices
KR102610947B1 (ko) 2015-01-30 2023-12-06 메르크 파텐트 게엠베하 낮은 입자 함유량을 갖는 조성물
JP6827938B2 (ja) 2015-01-30 2021-02-10 メルク パテント ゲーエムベーハー 電子素子のための材料
KR102554987B1 (ko) 2015-02-03 2023-07-12 메르크 파텐트 게엠베하 금속 착물
US10644247B2 (en) 2015-02-06 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US10418562B2 (en) 2015-02-06 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10355222B2 (en) 2015-02-06 2019-07-16 Universal Display Corporation Organic electroluminescent materials and devices
US10177316B2 (en) 2015-02-09 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10144867B2 (en) 2015-02-13 2018-12-04 Universal Display Corporation Organic electroluminescent materials and devices
JP5831654B1 (ja) 2015-02-13 2015-12-09 コニカミノルタ株式会社 芳香族複素環誘導体、それを用いた有機エレクトロルミネッセンス素子、照明装置及び表示装置
US10680183B2 (en) 2015-02-15 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US10903440B2 (en) 2015-02-24 2021-01-26 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
US10062861B2 (en) 2015-02-24 2018-08-28 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display device, electronic device, and lighting device
US11056657B2 (en) 2015-02-27 2021-07-06 University Display Corporation Organic electroluminescent materials and devices
US10600966B2 (en) 2015-02-27 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US10686143B2 (en) 2015-03-05 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
US10270046B2 (en) 2015-03-06 2019-04-23 Universal Display Corporation Organic electroluminescent materials and devices
TWI704706B (zh) 2015-03-09 2020-09-11 日商半導體能源研究所股份有限公司 發光元件、顯示裝置、電子裝置及照明設置
TWI779405B (zh) 2015-03-09 2022-10-01 日商半導體能源研究所股份有限公司 發光元件，顯示裝置，電子裝置，與照明裝置
US9911928B2 (en) 2015-03-19 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9871214B2 (en) 2015-03-23 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US10529931B2 (en) 2015-03-24 2020-01-07 Universal Display Corporation Organic Electroluminescent materials and devices
US10297770B2 (en) 2015-03-27 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
EP3279961B1 (en) * 2015-03-30 2023-07-19 NIPPON STEEL Chemical & Material Co., Ltd. Organic electroluminescent element
CN107431139B (zh) 2015-03-30 2020-12-01 默克专利有限公司 包含硅氧烷溶剂的有机功能材料的制剂
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US20160293855A1 (en) 2015-04-06 2016-10-06 Universal Display Corporation Organic Electroluminescent Materials and Devices
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US10777749B2 (en) 2015-05-07 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US10403826B2 (en) 2015-05-07 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US9478758B1 (en) 2015-05-08 2016-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
KR20240130152A (ko) 2015-05-21 2024-08-28 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 및 조명 장치
TWI757234B (zh) 2015-05-21 2022-03-11 日商半導體能源研究所股份有限公司 發光元件、顯示裝置、電子裝置、及照明裝置
US10256411B2 (en) 2015-05-21 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10109799B2 (en) 2015-05-21 2018-10-23 Universal Display Corporation Organic electroluminescent materials and devices
KR20180013958A (ko) 2015-05-29 2018-02-07 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 전자 기기, 및 조명 장치
US10418568B2 (en) 2015-06-01 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10033004B2 (en) 2015-06-01 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US10818853B2 (en) 2015-06-04 2020-10-27 University Of Southern California Organic electroluminescent materials and devices
US11925102B2 (en) 2015-06-04 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
EP3307735A1 (en) 2015-06-10 2018-04-18 Merck Patent GmbH Materials for organic electroluminescent devices
US10808170B2 (en) 2015-06-12 2020-10-20 Merck Patent Gmbh Esters containing non-aromatic cycles as solvents for OLED formulations
US10825997B2 (en) 2015-06-25 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10873036B2 (en) 2015-07-07 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US9978956B2 (en) 2015-07-15 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
KR102643183B1 (ko) 2015-07-15 2024-03-04 메르크 파텐트 게엠베하 유기 반도전성 화합물들을 포함하는 조성물
KR20240047495A (ko) 2015-07-21 2024-04-12 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 및 조명 장치
WO2017012687A1 (en) 2015-07-22 2017-01-26 Merck Patent Gmbh Materials for organic electroluminescent devices
GB201513037D0 (en) 2015-07-23 2015-09-09 Merck Patent Gmbh Phenyl-derived compound for use in organic electronic devices
KR20230048453A (ko) 2015-07-23 2023-04-11 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 및 조명 장치
US10700288B2 (en) 2015-07-24 2020-06-30 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, lighting device, and lighting system
JP6983754B2 (ja) 2015-07-29 2021-12-17 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
US11127905B2 (en) 2015-07-29 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
EP3328841B1 (en) 2015-07-30 2023-10-11 Merck Patent GmbH Materials for organic electroluminescent devices
US11018309B2 (en) 2015-08-03 2021-05-25 Universal Display Corporation Organic electroluminescent materials and devices
CN111710788B (zh) 2015-08-07 2023-07-21 株式会社半导体能源研究所 发光元件、显示装置、电子设备及照明装置
US10934292B2 (en) 2015-08-13 2021-03-02 Merck Patent Gmbh Hexamethylindanes
KR102599157B1 (ko) 2015-08-14 2023-11-06 메르크 파텐트 게엠베하 유기 전계발광 소자용 페녹사진 유도체
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US10522769B2 (en) 2015-08-18 2019-12-31 Universal Display Corporation Organic electroluminescent materials and devices
US10181564B2 (en) 2015-08-26 2019-01-15 Universal Display Corporation Organic electroluminescent materials and devices
US11046884B2 (en) 2015-08-28 2021-06-29 Merck Patent Gmbh Formulation of an organic functional material comprising an epoxy group containing solvent
WO2017036573A1 (en) 2015-08-28 2017-03-09 Merck Patent Gmbh Compounds for electronic devices
US10361381B2 (en) 2015-09-03 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US11706972B2 (en) 2015-09-08 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11302872B2 (en) 2015-09-09 2022-04-12 Universal Display Corporation Organic electroluminescent materials and devices
EP3141550B1 (en) * 2015-09-09 2020-03-18 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
KR102626916B1 (ko) * 2015-09-09 2024-01-19 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
US10770664B2 (en) 2015-09-21 2020-09-08 Universal Display Corporation Organic electroluminescent materials and devices
US20170092880A1 (en) 2015-09-25 2017-03-30 Universal Display Corporation Organic electroluminescent materials and devices
TW202425770A (zh) 2015-09-30 2024-06-16 日商半導體能源研究所股份有限公司 發光元件，顯示裝置，電子裝置，及照明裝置
KR20170038681A (ko) 2015-09-30 2017-04-07 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 및 조명 장치
US10593892B2 (en) 2015-10-01 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10847728B2 (en) 2015-10-01 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10991895B2 (en) 2015-10-06 2021-04-27 Universal Display Corporation Organic electroluminescent materials and devices
DE102015013381A1 (de) 2015-10-14 2017-04-20 Eberhard Karls Universität Tübingen Metallkomplexe
KR102678422B1 (ko) 2015-10-27 2024-06-25 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
US10388892B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10388893B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10177318B2 (en) 2015-10-29 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10998507B2 (en) 2015-11-23 2021-05-04 Universal Display Corporation Organic electroluminescent materials and devices
US10476010B2 (en) 2015-11-30 2019-11-12 Universal Display Corporation Organic electroluminescent materials and devices
DE112016005489B4 (de) 2015-12-01 2024-09-26 Semiconductor Energy Laboratory Co., Ltd. Licht emittierendes Element
JP7106451B2 (ja) 2015-12-10 2022-07-26 メルク パテント ゲーエムベーハー 非芳香族環を含むケトンを含む調合物
DE102015016016A1 (de) 2015-12-10 2017-06-14 Eberhard Karls Universität Tübingen Metallkomplexe
CN111477768B (zh) 2015-12-15 2023-04-07 默克专利有限公司 作为用于有机电子制剂的溶剂的含芳族基团的酯
US11407916B2 (en) 2015-12-16 2022-08-09 Merck Patent Gmbh Formulations containing a mixture of at least two different solvents
EP3390549B1 (en) 2015-12-16 2022-06-29 Merck Patent GmbH Formulations containing a solid solvent
CN106920883B (zh) 2015-12-25 2019-01-08 昆山工研院新型平板显示技术中心有限公司 一种有机电致发光器件
US11024808B2 (en) 2015-12-29 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US10957861B2 (en) 2015-12-29 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
JP6788314B2 (ja) 2016-01-06 2020-11-25 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置
JP7051691B2 (ja) 2016-02-05 2022-04-11 メルク パテント ゲーエムベーハー 電子素子のための材料
US20170229663A1 (en) 2016-02-09 2017-08-10 Universal Display Corporation Organic electroluminescent materials and devices
US10707427B2 (en) 2016-02-09 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US10457864B2 (en) 2016-02-09 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
WO2017140404A1 (en) 2016-02-17 2017-08-24 Merck Patent Gmbh Formulation of an organic functional material
US10600967B2 (en) 2016-02-18 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
WO2017148564A1 (de) 2016-03-03 2017-09-08 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
DE102016003104A1 (de) 2016-03-15 2017-09-21 Merck Patent Gmbh Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter
US11094891B2 (en) * 2016-03-16 2021-08-17 Universal Display Corporation Organic electroluminescent materials and devices
TWI745361B (zh) 2016-03-17 2021-11-11 德商麥克專利有限公司 具有螺聯茀結構之化合物
US10276809B2 (en) 2016-04-05 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
JP7444607B2 (ja) 2016-04-11 2024-03-06 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング ジベンゾフランおよび／またはジベンゾチオフェン構造を有する複素環式化合物
US10566552B2 (en) 2016-04-13 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US11228003B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US10096658B2 (en) 2016-04-22 2018-10-09 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display device, electronic device, and lighting device
US11081647B2 (en) 2016-04-22 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11228002B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11643414B2 (en) 2016-04-29 2023-05-09 Merck Patent Gmbh Materials for organic electroluminescent devices
DE102016108335B3 (de) * 2016-05-04 2016-12-22 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in organischen optoelektronischen Vorrichtungen
US20170324049A1 (en) 2016-05-05 2017-11-09 Universal Display Corporation Organic Electroluminescent Materials and Devices
US10756286B2 (en) 2016-05-06 2020-08-25 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display device, electronic device, and lighting device
KR102349892B1 (ko) 2016-05-06 2022-01-10 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 및 조명 장치
KR102289388B1 (ko) 2016-05-20 2021-08-11 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 및 조명 장치
US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10468609B2 (en) 2016-06-02 2019-11-05 Universal Display Corporation Organic electroluminescent materials and devices
TWI731981B (zh) 2016-06-03 2021-07-01 德商麥克專利有限公司 用於有機電激發光裝置之材料
KR20190019138A (ko) 2016-06-16 2019-02-26 메르크 파텐트 게엠베하 유기 기능성 재료의 제형
WO2017216128A1 (en) 2016-06-17 2017-12-21 Merck Patent Gmbh Formulation of an organic functional material
US10862054B2 (en) 2016-06-20 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US11482683B2 (en) 2016-06-20 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10686140B2 (en) 2016-06-20 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
US10727423B2 (en) 2016-06-20 2020-07-28 Universal Display Corporation Organic electroluminescent materials and devices
US10672997B2 (en) 2016-06-20 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10651403B2 (en) 2016-06-20 2020-05-12 Universal Display Corporation Organic electroluminescent materials and devices
TW201815998A (zh) 2016-06-28 2018-05-01 德商麥克專利有限公司 有機功能材料之調配物
EP3478698B1 (de) 2016-06-30 2021-01-13 Merck Patent GmbH Verfahren zur auftrennung von enantiomerenmischungen von metallkomplexen
US10988447B2 (en) * 2016-06-30 2021-04-27 Samsung Electronics Co., Ltd. Bipyridine derivatives and their uses for organic light emitting diodes
US10957866B2 (en) 2016-06-30 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
TWI745395B (zh) 2016-07-08 2021-11-11 德商麥克專利有限公司 有機電致發光裝置用之材料
US9929360B2 (en) 2016-07-08 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US10680184B2 (en) 2016-07-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
CN109415344B (zh) 2016-07-14 2022-06-03 默克专利有限公司 金属络合物
US10720587B2 (en) 2016-07-19 2020-07-21 Universal Display Corporation Organic electroluminescent materials and devices
US10153443B2 (en) 2016-07-19 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
KR20180010136A (ko) 2016-07-20 2018-01-30 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
WO2018019687A1 (de) 2016-07-25 2018-02-01 Merck Patent Gmbh Di- und oligonukleare metallkomplexe mit tripodalen bidentaten teilliganden sowie deren verwendung in elektronischen vorrichtungen
EP3487864B1 (de) 2016-07-25 2020-04-29 Merck Patent GmbH Metallkomplexe für den einsatz als emitter in organischen elektrolumineszenzvorrichtungen
JP6980757B2 (ja) 2016-08-04 2021-12-15 メルク パテント ゲーエムベーハー 有機機能材料の調合物
US10205105B2 (en) 2016-08-15 2019-02-12 Universal Display Corporation Organic electroluminescent materials and devices
WO2018033820A1 (en) 2016-08-17 2018-02-22 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
WO2018041769A1 (de) 2016-08-30 2018-03-08 Merck Patent Gmbh Bl- und trinukleare metallkomplexe aufgebaut aus zwei miteinander verknüpften tripodalen hexadentaten liganden zur verwendung in elektrolumineszenzvorrichtungen
KR102459000B1 (ko) 2016-09-14 2022-10-26 메르크 파텐트 게엠베하 카르바졸 구조를 갖는 화합물
EP3512841B1 (de) 2016-09-14 2023-04-26 Merck Patent GmbH Verbindungen mit spirobifluoren-strukturen
US10608186B2 (en) 2016-09-14 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10505127B2 (en) 2016-09-19 2019-12-10 Universal Display Corporation Organic electroluminescent materials and devices
CN109715642A (zh) 2016-09-21 2019-05-03 默克专利有限公司 用作有机电致发光器件中的发光体的双核金属络合物
US10680187B2 (en) 2016-09-23 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
CN113421989A (zh) 2016-09-29 2021-09-21 住友化学株式会社 发光元件及对于制造该发光元件而言有用的组合物
TWI766884B (zh) 2016-09-30 2022-06-11 德商麥克專利有限公司 具有二氮雜二苯并呋喃或二氮雜二苯并噻吩結構的化合物、其製法及其用途
KR20240033302A (ko) 2016-09-30 2024-03-12 메르크 파텐트 게엠베하 디아자디벤조푸란 또는 디아자디벤조티오펜 구조를 갖는 카르바졸
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US11189804B2 (en) 2016-10-03 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US11183642B2 (en) 2016-10-03 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11127906B2 (en) 2016-10-03 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11081658B2 (en) 2016-10-03 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
TWI764942B (zh) 2016-10-10 2022-05-21 德商麥克專利有限公司 電子裝置
JP7064487B2 (ja) 2016-10-12 2022-05-10 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 金属錯体
US11430962B2 (en) 2016-10-12 2022-08-30 Merck Patent Gmbh Binuclear metal complexes and electronic devices, in particular organic electroluminescent devices containing said metal complexes
EP3526226B1 (de) 2016-10-13 2020-07-22 Merck Patent GmbH Metallkomplexe
US11239432B2 (en) 2016-10-14 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US10608185B2 (en) 2016-10-17 2020-03-31 Univeral Display Corporation Organic electroluminescent materials and devices
DE102017008794A1 (de) 2016-10-17 2018-04-19 Merck Patent Gmbh Materialien zur Verwendung in elektronischen Vorrichtungen
US10236458B2 (en) 2016-10-24 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
WO2018077769A1 (de) 2016-10-25 2018-05-03 Merck Patent Gmbh Metallkomplexe
EP3532566B1 (en) 2016-10-31 2021-04-21 Merck Patent GmbH Formulation of an organic functional material
EP3532565B1 (en) 2016-10-31 2021-04-21 Merck Patent GmbH Formulation of an organic functional material
JP2020512273A (ja) 2016-11-02 2020-04-23 メルク パテント ゲーエムベーハー 電子デバイス用材料
US11440925B2 (en) 2016-11-08 2022-09-13 Merck Patent Gmbh Compounds for electronic devices
US20180130956A1 (en) 2016-11-09 2018-05-10 Universal Display Corporation Organic electroluminescent materials and devices
KR102474328B1 (ko) 2016-11-09 2022-12-06 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
US10340464B2 (en) 2016-11-10 2019-07-02 Universal Display Corporation Organic electroluminescent materials and devices
US10680188B2 (en) 2016-11-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10897016B2 (en) 2016-11-14 2021-01-19 Universal Display Corporation Organic electroluminescent materials and devices
TWI756292B (zh) 2016-11-14 2022-03-01 德商麥克專利有限公司 具有受體基團與供體基團之化合物
US10662196B2 (en) 2016-11-17 2020-05-26 Universal Display Corporation Organic electroluminescent materials and devices
KR102580980B1 (ko) 2016-11-17 2023-09-20 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
US10964893B2 (en) 2016-11-17 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US10153445B2 (en) 2016-11-21 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10833276B2 (en) 2016-11-21 2020-11-10 Universal Display Corporation Organic electroluminescent materials and devices
TW201833118A (zh) 2016-11-22 2018-09-16 德商麥克專利有限公司 用於電子裝置之材料
JP7127026B2 (ja) 2016-11-30 2022-08-29 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング バレロラクタム構造を有する化合物
US11555048B2 (en) 2016-12-01 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
TW201831468A (zh) 2016-12-05 2018-09-01 德商麥克專利有限公司 含氮的雜環化合物
EP3548486B1 (de) 2016-12-05 2021-10-27 Merck Patent GmbH Materialien für organische elektrolumineszenzvorrichtungen
WO2018104193A1 (de) 2016-12-05 2018-06-14 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
EP3552252B1 (en) 2016-12-06 2023-05-17 Merck Patent GmbH Preparation process for an electronic device
WO2018108760A1 (en) 2016-12-13 2018-06-21 Merck Patent Gmbh Formulation of an organic functional material
US10490753B2 (en) 2016-12-15 2019-11-26 Universal Display Corporation Organic electroluminescent materials and devices
US11548905B2 (en) 2016-12-15 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11545636B2 (en) 2016-12-15 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US10811618B2 (en) 2016-12-19 2020-10-20 Universal Display Corporation Organic electroluminescent materials and devices
WO2018114744A1 (en) 2016-12-20 2018-06-28 Merck Patent Gmbh A white light emitting solid state light source
KR102504432B1 (ko) 2016-12-22 2023-02-27 메르크 파텐트 게엠베하 적어도 2종의 유기-기능성 화합물을 포함하는 혼합물
US11261291B2 (en) 2016-12-22 2022-03-01 Merck Patent Gmbh Materials for electronic devices
US11152579B2 (en) 2016-12-28 2021-10-19 Universal Display Corporation Organic electroluminescent materials and devices
JP2020504762A (ja) 2017-01-04 2020-02-13 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイス用の材料
US11201298B2 (en) 2017-01-09 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US11780865B2 (en) 2017-01-09 2023-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US10804475B2 (en) 2017-01-11 2020-10-13 Universal Display Corporation Organic electroluminescent materials and devices
US11545637B2 (en) 2017-01-13 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US10629820B2 (en) 2017-01-18 2020-04-21 Universal Display Corporation Organic electroluminescent materials and devices
US10964904B2 (en) 2017-01-20 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US11053268B2 (en) 2017-01-20 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US11765968B2 (en) 2017-01-23 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11050028B2 (en) 2017-01-24 2021-06-29 Universal Display Corporation Organic electroluminescent materials and devices
US10964894B2 (en) 2017-01-25 2021-03-30 Merck Patent Gmbh Carbazole derivatives
TWI763772B (zh) 2017-01-30 2022-05-11 德商麥克專利有限公司 電子裝置之有機元件的形成方法
CN110167940A (zh) 2017-01-30 2019-08-23 默克专利有限公司 用于有机电致发光器件的材料
TWI791481B (zh) 2017-01-30 2023-02-11 德商麥克專利有限公司 形成有機電致發光（ｅｌ）元件之方法
JP7069184B2 (ja) 2017-02-02 2022-05-17 メルク パテント ゲーエムベーハー 電子デバイス用材料
US12089486B2 (en) 2017-02-08 2024-09-10 Universal Display Corporation Organic electroluminescent materials and devices
TW201835075A (zh) 2017-02-14 2018-10-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
US10978647B2 (en) 2017-02-15 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US10844084B2 (en) 2017-02-22 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US11393987B2 (en) 2017-03-01 2022-07-19 Merck Patent Gmbh Organic electroluminescent device
EP3589624A1 (de) 2017-03-02 2020-01-08 Merck Patent GmbH Materialien für organische elektronische vorrichtungen
US10186668B2 (en) 2017-03-04 2019-01-22 Feng-wen Yen Organic electroluminescent material and use thereof
US10745431B2 (en) 2017-03-08 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10741780B2 (en) 2017-03-10 2020-08-11 Universal Display Corporation Organic electroluminescent materials and devices
TW201843143A (zh) 2017-03-13 2018-12-16 德商麥克專利有限公司 含有芳基胺結構之化合物
JP7155142B2 (ja) 2017-03-15 2022-10-18 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセントデバイス用の材料
US10672998B2 (en) 2017-03-23 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10910577B2 (en) 2017-03-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US10873037B2 (en) 2017-03-28 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10844085B2 (en) 2017-03-29 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US11056658B2 (en) 2017-03-29 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US11158820B2 (en) 2017-03-29 2021-10-26 Universal Display Corporation Organic electroluminescent materials and devices
CN110446703A (zh) 2017-03-29 2019-11-12 默克专利有限公司 芳族化合物
US10862046B2 (en) 2017-03-30 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
CN106977514A (zh) * 2017-03-30 2017-07-25 上海道亦化工科技有限公司 一种含有咔唑衍生物的有机电致发光化合物及其发光器件
US11139443B2 (en) 2017-03-31 2021-10-05 Universal Display Corporation Organic electroluminescent materials and devices
KR20190131554A (ko) 2017-03-31 2019-11-26 메르크 파텐트 게엠베하 유기 발광 다이오드 (oled) 를 위한 인쇄 방법
US11276829B2 (en) 2017-03-31 2022-03-15 Universal Display Corporation Organic electroluminescent materials and devices
KR102632027B1 (ko) 2017-04-10 2024-01-31 메르크 파텐트 게엠베하 유기 기능성 재료의 제형
US11038117B2 (en) 2017-04-11 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US10777754B2 (en) 2017-04-11 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
TW201902891A (zh) 2017-04-13 2019-01-16 德商麥克專利有限公司 用於有機電子裝置之組成物
US11084838B2 (en) 2017-04-21 2021-08-10 Universal Display Corporation Organic electroluminescent materials and device
US10975113B2 (en) 2017-04-21 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US11101434B2 (en) 2017-04-21 2021-08-24 Universal Display Corporation Organic electroluminescent materials and devices
EP3615542B1 (de) 2017-04-25 2023-08-23 Merck Patent GmbH Verbindungen für elektronische vorrichtungen
US10910570B2 (en) 2017-04-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US11038137B2 (en) 2017-04-28 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US11117897B2 (en) 2017-05-01 2021-09-14 Universal Display Corporation Organic electroluminescent materials and devices
CN110546236A (zh) 2017-05-03 2019-12-06 默克专利有限公司 有机功能材料的制剂
US10941170B2 (en) 2017-05-03 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US11201299B2 (en) 2017-05-04 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US10870668B2 (en) 2017-05-05 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10862055B2 (en) 2017-05-05 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10930864B2 (en) 2017-05-10 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
EP3621971B1 (en) 2017-05-11 2021-06-23 Merck Patent GmbH Carbazole-based bodipys for organic electroluminescent devices
US10822362B2 (en) 2017-05-11 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
EP3621970B1 (en) 2017-05-11 2021-01-13 Merck Patent GmbH Organoboron complexes for organic electroluminescent devices
US10944060B2 (en) 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10934293B2 (en) 2017-05-18 2021-03-02 Universal Display Corporation Organic electroluminescent materials and devices
US11038115B2 (en) 2017-05-18 2021-06-15 Universal Display Corporation Organic electroluminescent materials and device
US10840459B2 (en) 2017-05-18 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10944062B2 (en) 2017-05-18 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10790455B2 (en) 2017-05-18 2020-09-29 Universal Display Corporation Organic electroluminescent materials and devices
WO2018215318A1 (de) 2017-05-22 2018-11-29 Merck Patent Gmbh Hexazyklische heteroaromatische verbindungen für elektronische vorrichtungen
US10930862B2 (en) 2017-06-01 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
TW201920343A (zh) 2017-06-21 2019-06-01 德商麥克專利有限公司 電子裝置用材料
US11678565B2 (en) 2017-06-23 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US12098157B2 (en) 2017-06-23 2024-09-24 Universal Display Corporation Organic electroluminescent materials and devices
US10968226B2 (en) 2017-06-23 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US11758804B2 (en) 2017-06-23 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
EP3418278B1 (en) * 2017-06-23 2020-10-21 Cynora Gmbh Organic molecules, in particular for use in optoelectronic devices
US11725022B2 (en) 2017-06-23 2023-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US11832510B2 (en) 2017-06-23 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
TW201920598A (zh) 2017-06-23 2019-06-01 德商麥克專利有限公司 用於有機電激發光裝置之材料
US11495757B2 (en) 2017-06-23 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11174259B2 (en) 2017-06-23 2021-11-16 Universal Display Corporation Organic electroluminescent materials and devices
US11552261B2 (en) 2017-06-23 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11802136B2 (en) 2017-06-23 2023-10-31 Universal Display Corporation Organic electroluminescent materials and devices
US11814403B2 (en) 2017-06-23 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11608321B2 (en) 2017-06-23 2023-03-21 Universal Display Corporation Organic electroluminescent materials and devices
KR20200022010A (ko) 2017-06-26 2020-03-02 메르크 파텐트 게엠베하 균질 혼합물
KR102661058B1 (ko) 2017-06-28 2024-04-25 메르크 파텐트 게엠베하 전자 디바이스용 재료
TWI813576B (zh) 2017-07-03 2023-09-01 德商麥克專利有限公司 具有低含量苯酚類雜質的調配物
KR102717279B1 (ko) 2017-07-05 2024-10-15 메르크 파텐트 게엠베하 유기 전자 디바이스용 조성물
WO2019007867A1 (de) 2017-07-05 2019-01-10 Merck Patent Gmbh Zusammensetzung für organische elektronische vorrichtungen
US11469382B2 (en) 2017-07-12 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
WO2019016184A1 (en) 2017-07-18 2019-01-24 Merck Patent Gmbh FORMULATION OF AN ORGANIC FUNCTIONAL MATERIAL
TWI776926B (zh) 2017-07-25 2022-09-11 德商麥克專利有限公司 金屬錯合物
US11968883B2 (en) 2017-07-26 2024-04-23 Universal Display Corporation Organic electroluminescent materials and devices
US11228010B2 (en) 2017-07-26 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11322691B2 (en) 2017-07-26 2022-05-03 Universal Display Corporation Organic electroluminescent materials and devices
US11917843B2 (en) 2017-07-26 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11765970B2 (en) 2017-07-26 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11239433B2 (en) 2017-07-26 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
WO2019020654A1 (en) 2017-07-28 2019-01-31 Merck Patent Gmbh SPIROBIFLUORENE DERIVATIVES FOR USE IN ELECTRONIC DEVICES
US11744141B2 (en) 2017-08-09 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11910699B2 (en) 2017-08-10 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US11349083B2 (en) 2017-08-10 2022-05-31 Universal Display Corporation Organic electroluminescent materials and devices
US11508913B2 (en) 2017-08-10 2022-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11462697B2 (en) 2017-08-22 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11723269B2 (en) 2017-08-22 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11437591B2 (en) 2017-08-24 2022-09-06 Universal Display Corporation Organic electroluminescent materials and devices
US11605791B2 (en) 2017-09-01 2023-03-14 Universal Display Corporation Organic electroluminescent materials and devices
EP3680945B1 (en) 2017-09-06 2023-09-06 Sumitomo Chemical Company Limited Light emitting element
US11424420B2 (en) 2017-09-07 2022-08-23 Universal Display Corporation Organic electroluminescent materials and devices
US11444249B2 (en) 2017-09-07 2022-09-13 Universal Display Corporation Organic electroluminescent materials and devices
US11696492B2 (en) 2017-09-07 2023-07-04 Universal Display Corporation Organic electroluminescent materials and devices
CN118405981A (zh) 2017-09-08 2024-07-30 默克专利有限公司 用于电子器件的材料
US10608188B2 (en) 2017-09-11 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
CN111065640B (zh) 2017-09-12 2023-04-18 默克专利有限公司 用于有机电致发光器件的材料
CN111051470B (zh) 2017-09-14 2020-11-10 住友化学株式会社 用于制备液体组合物的方法
US11778897B2 (en) 2017-09-20 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
CN111164086A (zh) 2017-10-06 2020-05-15 默克专利有限公司 用于有机电致发光器件的材料
CN108675975A (zh) 2017-10-17 2018-10-19 默克专利有限公司 用于有机电致发光器件的材料
EP3700909B1 (de) 2017-10-24 2024-01-24 Merck Patent GmbH Materialien für organische elektrolumineszenzvorrichtungen
WO2019087003A1 (en) 2017-11-02 2019-05-09 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display device, electronic device, and lighting device
US11910702B2 (en) 2017-11-07 2024-02-20 Universal Display Corporation Organic electroluminescent devices
US11183646B2 (en) 2017-11-07 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11214587B2 (en) 2017-11-07 2022-01-04 Universal Display Corporation Organic electroluminescent materials and devices
TWI785142B (zh) 2017-11-14 2022-12-01 德商麥克專利有限公司 用於有機電子裝置之組成物
US11168103B2 (en) 2017-11-17 2021-11-09 Universal Display Corporation Organic electroluminescent materials and devices
KR20200090817A (ko) 2017-11-23 2020-07-29 메르크 파텐트 게엠베하 전자 디바이스용 재료
TWI838352B (zh) 2017-11-24 2024-04-11 德商麥克專利有限公司 用於有機電致發光裝置的材料
TWI820057B (zh) 2017-11-24 2023-11-01 德商麥克專利有限公司 用於有機電致發光裝置的材料
US11825735B2 (en) 2017-11-28 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US20190161504A1 (en) 2017-11-28 2019-05-30 University Of Southern California Carbene compounds and organic electroluminescent devices
EP3492480B1 (en) 2017-11-29 2021-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US11937503B2 (en) 2017-11-30 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
WO2019115423A1 (de) 2017-12-13 2019-06-20 Merck Patent Gmbh Metallkomplexe
US11233205B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11233204B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US10971687B2 (en) 2017-12-14 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US12075690B2 (en) 2017-12-14 2024-08-27 Universal Display Corporation Organic electroluminescent materials and devices
WO2019115573A1 (en) 2017-12-15 2019-06-20 Merck Patent Gmbh Formulation of an organic functional material
EP3724175A1 (en) 2017-12-15 2020-10-21 Merck Patent GmbH Substituted aromatic amines for use in organic electroluminescent devices
TW201938562A (zh) 2017-12-19 2019-10-01 德商麥克專利有限公司 雜環化合物
WO2019121483A1 (en) 2017-12-20 2019-06-27 Merck Patent Gmbh Heteroaromatic compounds
US11700765B2 (en) 2018-01-10 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11081659B2 (en) 2018-01-10 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11271177B2 (en) 2018-01-11 2022-03-08 Universal Display Corporation Organic electroluminescent materials and devices
US11515493B2 (en) 2018-01-11 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11462696B2 (en) 2018-01-19 2022-10-04 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
TWI811290B (zh) 2018-01-25 2023-08-11 德商麥克專利有限公司 用於有機電致發光裝置的材料
US11845764B2 (en) 2018-01-26 2023-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11367840B2 (en) 2018-01-26 2022-06-21 Universal Display Corporation Organic electroluminescent materials and devices
US11542289B2 (en) 2018-01-26 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US12029055B2 (en) 2018-01-30 2024-07-02 The University Of Southern California OLED with hybrid emissive layer
US11180519B2 (en) 2018-02-09 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11342509B2 (en) 2018-02-09 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11957050B2 (en) 2018-02-09 2024-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US11239434B2 (en) 2018-02-09 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
EP3752512B1 (de) 2018-02-13 2023-03-01 Merck Patent GmbH Metallkomplexe
CN111712551A (zh) 2018-02-26 2020-09-25 默克专利有限公司 有机功能材料的制剂
TW201938761A (zh) 2018-03-06 2019-10-01 德商麥克專利有限公司 用於有機電致發光裝置的材料
TWI802656B (zh) 2018-03-06 2023-05-21 德商麥克專利有限公司 用於有機電致發光裝置之材料
KR20200130348A (ko) 2018-03-07 2020-11-18 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 유기 화합물, 및 조명 장치
US11557733B2 (en) 2018-03-12 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11165028B2 (en) 2018-03-12 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
US11217757B2 (en) 2018-03-12 2022-01-04 Universal Display Corporation Host materials for electroluminescent devices
US11142538B2 (en) 2018-03-12 2021-10-12 Universal Display Corporation Organic electroluminescent materials and devices
US11279722B2 (en) 2018-03-12 2022-03-22 Universal Display Corporation Organic electroluminescent materials and devices
CN111819167A (zh) 2018-03-16 2020-10-23 默克专利有限公司 用于有机电致发光器件的材料
TWI828664B (zh) 2018-03-19 2024-01-11 愛爾蘭商Ｕｄｃ愛爾蘭責任有限公司 金屬錯合物
KR102703716B1 (ko) * 2018-04-09 2024-09-06 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
US11390639B2 (en) 2018-04-13 2022-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US11882759B2 (en) 2018-04-13 2024-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US11616203B2 (en) 2018-04-17 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US11753427B2 (en) 2018-05-04 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11515494B2 (en) 2018-05-04 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11342513B2 (en) 2018-05-04 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11793073B2 (en) 2018-05-06 2023-10-17 Universal Display Corporation Host materials for electroluminescent devices
US11450822B2 (en) 2018-05-25 2022-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US11459349B2 (en) 2018-05-25 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
EP3802520A1 (de) 2018-05-30 2021-04-14 Merck Patent GmbH Zusammensetzung für organische elektronische vorrichtungen
US11716900B2 (en) 2018-05-30 2023-08-01 Universal Display Corporation Host materials for electroluminescent devices
US11404653B2 (en) 2018-06-04 2022-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US11925103B2 (en) 2018-06-05 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11339182B2 (en) 2018-06-07 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US20220336754A1 (en) 2018-06-07 2022-10-20 Merck Patent Gmbh Organic electroluminescence devices
JP6657487B1 (ja) 2018-06-12 2020-03-04 住友化学株式会社 有機エレクトロルミネッセンス素子
TWI835803B (zh) 2018-06-15 2024-03-21 德商麥克專利有限公司 有機功能性材料之調配物
US11228004B2 (en) 2018-06-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11261207B2 (en) 2018-06-25 2022-03-01 Universal Display Corporation Organic electroluminescent materials and devices
KR20210031714A (ko) 2018-07-09 2021-03-22 메르크 파텐트 게엠베하 유기 전계발광 디바이스용 재료
US11753425B2 (en) 2018-07-11 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
CN112424169A (zh) 2018-07-20 2021-02-26 默克专利有限公司 用于有机电致发光器件的材料
US20200075870A1 (en) 2018-08-22 2020-03-05 Universal Display Corporation Organic electroluminescent materials and devices
TWI823993B (zh) 2018-08-28 2023-12-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
EP3844243B1 (en) 2018-08-28 2022-06-22 Merck Patent GmbH Materials for organic electroluminescent devices
TWI837167B (zh) 2018-08-28 2024-04-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
US11233203B2 (en) 2018-09-06 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11485706B2 (en) 2018-09-11 2022-11-01 Universal Display Corporation Organic electroluminescent materials and devices
TWI826522B (zh) 2018-09-12 2023-12-21 德商麥克專利有限公司 電致發光裝置
TW202030902A (zh) 2018-09-12 2020-08-16 德商麥克專利有限公司 電致發光裝置
EP3850055A1 (en) 2018-09-12 2021-07-21 Merck Patent GmbH Materials for organic electroluminescent devices
US11718634B2 (en) 2018-09-14 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11903305B2 (en) 2018-09-24 2024-02-13 Universal Display Corporation Organic electroluminescent materials and devices
JP2022502829A (ja) 2018-09-24 2022-01-11 メルク パテント ゲーエムベーハー 粒状材料を製造するための方法
CN112771024A (zh) 2018-09-27 2021-05-07 默克专利有限公司 用于制备空间位阻型含氮杂芳族化合物的方法
KR20210068054A (ko) 2018-09-27 2021-06-08 메르크 파텐트 게엠베하 유기 전자 디바이스에서 활성 화합물로 사용될 수 있는 화합물
US11469383B2 (en) 2018-10-08 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11495752B2 (en) 2018-10-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11476430B2 (en) 2018-10-15 2022-10-18 Universal Display Corporation Organic electroluminescent materials and devices
US11515482B2 (en) 2018-10-23 2022-11-29 Universal Display Corporation Deep HOMO (highest occupied molecular orbital) emitter device structures
US20220223801A1 (en) 2018-10-31 2022-07-14 Merck Patent Gmbh Materials for organic electroluminescent devices
US11469384B2 (en) 2018-11-02 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
WO2020094539A1 (de) 2018-11-05 2020-05-14 Merck Patent Gmbh In einer organischen elektronischen vorrichtung einsetzbare verbindungen
TWI846749B (zh) 2018-11-06 2024-07-01 德商麥克專利有限公司 用於形成電子裝置的有機元件之方法以及墨水套組
KR20210089205A (ko) 2018-11-06 2021-07-15 메르크 파텐트 게엠베하 Oled 용 유기 전계 발광 재료로서 5,6-디페닐-5,6-디히드로디벤즈[c,e][1,2]아자포스포린 및 6-페닐-6h-디벤조[c,e][1,2]티아진-5,5-디옥사이드 유도체 및 유사한 화합물
KR20210091769A (ko) 2018-11-14 2021-07-22 메르크 파텐트 게엠베하 유기 전자 디바이스의 제조에 사용될 수 있는 화합물
EP3880682B1 (de) 2018-11-15 2023-06-14 Merck Patent GmbH Materialien für organische elektrolumineszenzvorrichtungen
US11825736B2 (en) 2018-11-19 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11963441B2 (en) 2018-11-26 2024-04-16 Universal Display Corporation Organic electroluminescent materials and devices
US11690285B2 (en) 2018-11-28 2023-06-27 Universal Display Corporation Electroluminescent devices
US11672176B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Host materials for electroluminescent devices
US11706980B2 (en) 2018-11-28 2023-07-18 Universal Display Corporation Host materials for electroluminescent devices
US11889708B2 (en) 2019-11-14 2024-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US11716899B2 (en) 2018-11-28 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US11672165B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US11623936B2 (en) 2018-12-11 2023-04-11 Universal Display Corporation Organic electroluminescent materials and devices
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
US11737349B2 (en) 2018-12-12 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
TW202039493A (zh) 2018-12-19 2020-11-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
WO2020148243A1 (en) 2019-01-16 2020-07-23 Merck Patent Gmbh Materials for organic electroluminescent devices
US11812624B2 (en) 2019-01-30 2023-11-07 The University Of Southern California Organic electroluminescent materials and devices
US11780829B2 (en) 2019-01-30 2023-10-10 The University Of Southern California Organic electroluminescent materials and devices
US20200251664A1 (en) 2019-02-01 2020-08-06 Universal Display Corporation Organic electroluminescent materials and devices
CN113412508A (zh) 2019-02-06 2021-09-17 株式会社半导体能源研究所 发光器件、发光设备、显示装置、电子设备及照明装置
US11370809B2 (en) 2019-02-08 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11325932B2 (en) 2019-02-08 2022-05-10 Universal Display Corporation Organic electroluminescent materials and devices
US20220098477A1 (en) 2019-02-11 2022-03-31 Merck Patent Gmbh Mononuclear iridium complexes containing three ortho-metallated bidentate ligands and optical orientating anistrophy
JP2022520284A (ja) 2019-02-18 2022-03-29 メルク パテント ゲーエムベーハー 有機電子デバイス用の組成物
US11773320B2 (en) 2019-02-21 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11871653B2 (en) 2019-02-22 2024-01-09 Universal Display Corporation Organic electroluminescent materials and devices
US11758807B2 (en) 2019-02-22 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11512093B2 (en) 2019-03-04 2022-11-29 Universal Display Corporation Compound used for organic light emitting device (OLED), consumer product and formulation
US20220127286A1 (en) 2019-03-04 2022-04-28 Merck Patent Gmbh Ligands for nano-sized materials
US11739081B2 (en) 2019-03-11 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
KR20210137148A (ko) 2019-03-12 2021-11-17 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 재료
US11637261B2 (en) 2019-03-12 2023-04-25 Universal Display Corporation Nanopatch antenna outcoupling structure for use in OLEDs
US12082428B2 (en) 2019-03-12 2024-09-03 Universal Display Corporation OLED with triplet emitter and excited state lifetime less than 200 ns
US11569480B2 (en) 2019-03-12 2023-01-31 Universal Display Corporation Plasmonic OLEDs and vertical dipole emitters
CN113508117A (zh) 2019-03-20 2021-10-15 默克专利有限公司 用于有机电致发光器件的材料
WO2020193447A1 (de) 2019-03-25 2020-10-01 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
KR20200115795A (ko) * 2019-03-26 2020-10-08 삼성디스플레이 주식회사 유기 발광 소자 및 전자 장치
US11963438B2 (en) 2019-03-26 2024-04-16 The University Of Southern California Organic electroluminescent materials and devices
JP2020158491A (ja) 2019-03-26 2020-10-01 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料及びデバイス
US12122793B2 (en) 2019-03-27 2024-10-22 Universal Display Corporation Organic electroluminescent materials and devices
JP6894025B2 (ja) 2019-03-29 2021-06-23 住友化学株式会社 発光素子及びその製造方法並びに発光素子用組成物及びその製造方法
JP2022527591A (ja) 2019-04-11 2022-06-02 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機エレクトロルミネッセンス素子のための材料
WO2020212296A1 (de) 2019-04-15 2020-10-22 Merck Patent Gmbh Metallkomplexe
US11639363B2 (en) 2019-04-22 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US11613550B2 (en) 2019-04-30 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes
US12075691B2 (en) 2019-04-30 2024-08-27 Universal Display Corporation Organic electroluminescent materials and devices
US11495756B2 (en) 2019-05-07 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11560398B2 (en) 2019-05-07 2023-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US12103942B2 (en) 2019-05-13 2024-10-01 Universal Display Corporation Organic electroluminescent materials and devices
US11827651B2 (en) 2019-05-13 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11634445B2 (en) 2019-05-21 2023-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US12010859B2 (en) 2019-05-24 2024-06-11 Universal Display Corporation Organic electroluminescent materials and devices
JP7289729B2 (ja) * 2019-05-31 2023-06-12 キヤノン株式会社 有機化合物及び有機発光素子
US11647667B2 (en) 2019-06-14 2023-05-09 Universal Display Corporation Organic electroluminescent compounds and organic light emitting devices using the same
US12077550B2 (en) 2019-07-02 2024-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US11920070B2 (en) 2019-07-12 2024-03-05 The University Of Southern California Luminescent janus-type, two-coordinated metal complexes
US11685754B2 (en) 2019-07-22 2023-06-27 Universal Display Corporation Heteroleptic organic electroluminescent materials
US11926638B2 (en) 2019-07-22 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US20210032278A1 (en) 2019-07-30 2021-02-04 Universal Display Corporation Organic electroluminescent materials and devices
US11708355B2 (en) 2019-08-01 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11985888B2 (en) 2019-08-12 2024-05-14 The Regents Of The University Of Michigan Organic electroluminescent device
US11374181B2 (en) 2019-08-14 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11930699B2 (en) 2019-08-15 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
JP2021031490A (ja) 2019-08-16 2021-03-01 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料及びデバイス
US11925105B2 (en) 2019-08-26 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
WO2021037401A1 (de) 2019-08-26 2021-03-04 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
US11937494B2 (en) 2019-08-28 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11600787B2 (en) 2019-08-30 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
WO2021043703A1 (de) 2019-09-02 2021-03-11 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
TW202122558A (zh) 2019-09-03 2021-06-16 德商麥克專利有限公司 用於有機電致發光裝置之材料
US11820783B2 (en) 2019-09-06 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
CN114450286A (zh) 2019-09-16 2022-05-06 默克专利有限公司 有机电致发光器件的材料
CN114342103A (zh) 2019-09-19 2022-04-12 默克专利有限公司 两种主体材料的混合物和包含所述混合物的有机电致发光器件
WO2021053046A1 (de) 2019-09-20 2021-03-25 Merck Patent Gmbh Peri-kondensierte heterozyklische verbindungen als materialien für elektronische vorrichtungen
US11999886B2 (en) 2019-09-26 2024-06-04 Universal Display Corporation Organic electroluminescent materials and devices
US11864458B2 (en) 2019-10-08 2024-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US11950493B2 (en) 2019-10-15 2024-04-02 Universal Display Corporation Organic electroluminescent materials and devices
US11697653B2 (en) 2019-10-21 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
CN114514628A (zh) 2019-10-22 2022-05-17 默克专利有限公司 用于有机电致发光器件的材料
US11919914B2 (en) 2019-10-25 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
KR20220090539A (ko) 2019-10-25 2022-06-29 메르크 파텐트 게엠베하 유기 전자 디바이스에서 사용될 수 있는 화합물
US11765965B2 (en) 2019-10-30 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
WO2021089450A1 (en) 2019-11-04 2021-05-14 Merck Patent Gmbh Materials for organic electroluminescent devices
US20210135130A1 (en) 2019-11-04 2021-05-06 Universal Display Corporation Organic electroluminescent materials and devices
TW202134252A (zh) 2019-11-12 2021-09-16 德商麥克專利有限公司 有機電致發光裝置用材料
JP7488091B2 (ja) 2019-11-14 2024-05-21 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料及びデバイス
US20230056324A1 (en) 2019-12-04 2023-02-23 Merck Patent Gmbh Metal complexes
TW202136181A (zh) 2019-12-04 2021-10-01 德商麥克專利有限公司 有機電致發光裝置用的材料
TW202136471A (zh) 2019-12-17 2021-10-01 德商麥克專利有限公司 有機電致發光裝置用的材料
WO2021122538A1 (de) 2019-12-18 2021-06-24 Merck Patent Gmbh Aromatische verbindungen für organische elektrolumineszenzvorrichtungen
CN114867729A (zh) 2019-12-19 2022-08-05 默克专利有限公司 用于有机电致发光器件的多环化合物
US20210217969A1 (en) 2020-01-06 2021-07-15 Universal Display Corporation Organic electroluminescent materials and devices
US11778895B2 (en) 2020-01-13 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11917900B2 (en) 2020-01-28 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US20220336759A1 (en) 2020-01-28 2022-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US11932660B2 (en) 2020-01-29 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
CN115052865A (zh) 2020-01-29 2022-09-13 默克专利有限公司 苯并咪唑衍生物
US12084465B2 (en) 2020-02-24 2024-09-10 Universal Display Corporation Organic electroluminescent materials and devices
EP4110884A1 (de) 2020-02-25 2023-01-04 Merck Patent GmbH Verwendung von heterocyclischen verbindungen in einer organischen elektronischen vorrichtung
CN115244728A (zh) 2020-03-02 2022-10-25 默克专利有限公司 砜化合物在有机电子器件中的用途
US20230147279A1 (en) 2020-03-17 2023-05-11 Merck Patent Gmbh Heterocyclic compounds for organic electroluminescent devices
EP4121432A1 (de) 2020-03-17 2023-01-25 Merck Patent GmbH Heteroaromatische verbindungen für organische elektrolumineszenzvorrichtungen
US20230337537A1 (en) 2020-03-23 2023-10-19 Merck Patent Gmbh Materials for organic electroluminescent devices
US12018035B2 (en) 2020-03-23 2024-06-25 Universal Display Corporation Organic electroluminescent materials and devices
KR20220158017A (ko) 2020-03-24 2022-11-29 메르크 파텐트 게엠베하 전자 디바이스용 재료
KR20220158771A (ko) 2020-03-26 2022-12-01 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 환형 화합물
EP4126870A1 (de) 2020-04-02 2023-02-08 Merck Patent GmbH Materialien für organische elektrolumineszenzvorrichtungen
CN115362159A (zh) 2020-04-06 2022-11-18 默克专利有限公司 用于有机电致发光器件的多环化合物
US12129269B2 (en) 2020-04-13 2024-10-29 Universal Display Corporation Organic electroluminescent materials and devices
WO2021213918A1 (en) 2020-04-21 2021-10-28 Merck Patent Gmbh Formulation of an organic functional material
CN115700058A (zh) 2020-04-21 2023-02-03 默克专利有限公司 包含有机功能材料的乳液
US11970508B2 (en) 2020-04-22 2024-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US12035613B2 (en) 2020-05-26 2024-07-09 Universal Display Corporation Organic electroluminescent materials and devices
TW202208594A (zh) 2020-05-27 2022-03-01 德商麥克專利有限公司 電子裝置用材料
US20230234937A1 (en) 2020-06-18 2023-07-27 Merck Patent Gmbh Indenoazanaphthalenes
EP4169082A1 (de) 2020-06-23 2023-04-26 Merck Patent GmbH Verfahren zur herstellung einer mischung
EP4172164A1 (de) 2020-06-29 2023-05-03 Merck Patent GmbH Heteroaromatische verbindungen für organische elektrolumineszenzvorrichtungen
JP2023530915A (ja) 2020-06-29 2023-07-20 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機エレクトロルミネッセンス素子のためのヘテロ環式化合物
EP3937268A1 (en) 2020-07-10 2022-01-12 Universal Display Corporation Plasmonic oleds and vertical dipole emitters
TW202216952A (zh) 2020-07-22 2022-05-01 德商麥克專利有限公司 用於有機電發光裝置之材料
JP2022024744A (ja) 2020-07-28 2022-02-09 住友化学株式会社 組成物及び発光素子
WO2022029096A1 (de) 2020-08-06 2022-02-10 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
CN116134113A (zh) 2020-08-13 2023-05-16 默克专利有限公司 金属络合物
WO2022038065A1 (de) 2020-08-18 2022-02-24 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
US12065451B2 (en) 2020-08-19 2024-08-20 Universal Display Corporation Organic electroluminescent materials and devices
TW202223066A (zh) 2020-08-19 2022-06-16 德商麥克專利有限公司 用於有機電致發光裝置之材料
KR20230077726A (ko) 2020-09-18 2023-06-01 삼성디스플레이 주식회사 유기 전계 발광 소자
EP4222155A1 (de) 2020-09-29 2023-08-09 Merck Patent GmbH Mononukleare tripodale hexadentate iridium komplexe zur verwendung in oleds
TW202229215A (zh) 2020-09-30 2022-08-01 德商麥克專利有限公司 用於有機電致發光裝置功能層之結構化的化合物
TW202222748A (zh) 2020-09-30 2022-06-16 德商麥克專利有限公司 用於結構化有機電致發光裝置的功能層之化合物
US20230389423A1 (en) 2020-10-16 2023-11-30 Merck Patent Gmbh Heterocyclic compounds for organic electroluminescent devices
EP4229145A1 (de) 2020-10-16 2023-08-23 Merck Patent GmbH Verbindungen mit heteroatomen für organische elektrolumineszenzvorrichtungen
US20230422610A1 (en) 2020-11-10 2023-12-28 Merck Patent Gmbh Sulfurous compounds for organic electroluminescent devices
US20220158096A1 (en) 2020-11-16 2022-05-19 Universal Display Corporation Organic electroluminescent materials and devices
US20220162243A1 (en) 2020-11-24 2022-05-26 Universal Display Corporation Organic electroluminescent materials and devices
US20220165967A1 (en) 2020-11-24 2022-05-26 Universal Display Corporation Organic electroluminescent materials and devices
EP4255905A1 (de) 2020-12-02 2023-10-11 Merck Patent GmbH Heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen
KR20230114756A (ko) 2020-12-08 2023-08-01 메르크 파텐트 게엠베하 잉크 시스템 및 잉크젯 인쇄를 위한 방법
WO2022122682A2 (de) 2020-12-10 2022-06-16 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
CN116724040A (zh) 2020-12-18 2023-09-08 默克专利有限公司 用于有机电致发光器件的含氮化合物
WO2022129113A1 (de) 2020-12-18 2022-06-23 Merck Patent Gmbh Stickstoffhaltige heteroaromaten für organische elektrolumineszenzvorrichtungen
WO2022129116A1 (de) 2020-12-18 2022-06-23 Merck Patent Gmbh Indolo[3.2.1-jk]carbazole-6-carbonitril-derivate als blau fluoreszierende emitter zur verwendung in oleds
JP2024502093A (ja) 2021-01-05 2024-01-17 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセントデバイスのための材料
KR20230137375A (ko) 2021-01-25 2023-10-04 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 질소 화합물
CN114105997B (zh) * 2021-01-28 2023-05-19 陕西莱特光电材料股份有限公司 一种含氮化合物及包含其的电子元件和电子装置
US20220271241A1 (en) 2021-02-03 2022-08-25 Universal Display Corporation Organic electroluminescent materials and devices
JP2024501664A (ja) * 2021-02-26 2024-01-15 エルジー・ケム・リミテッド 有機発光素子
EP4059915A3 (en) 2021-02-26 2022-12-28 Universal Display Corporation Organic electroluminescent materials and devices
EP4060758A3 (en) 2021-02-26 2023-03-29 Universal Display Corporation Organic electroluminescent materials and devices
WO2022184601A1 (de) 2021-03-02 2022-09-09 Merck Patent Gmbh Verbindungen für organische elektrolumineszenzvorrichtungen
US20220298192A1 (en) 2021-03-05 2022-09-22 Universal Display Corporation Organic electroluminescent materials and devices
US20220298190A1 (en) 2021-03-12 2022-09-22 Universal Display Corporation Organic electroluminescent materials and devices
US20220298193A1 (en) 2021-03-15 2022-09-22 Universal Display Corporation Organic electroluminescent materials and devices
WO2022194799A1 (de) 2021-03-18 2022-09-22 Merck Patent Gmbh Heteroaromatische verbindungen für organische elektrolumineszenzvorrichtungen
US20220340607A1 (en) 2021-04-05 2022-10-27 Universal Display Corporation Organic electroluminescent materials and devices
EP4075531A1 (en) 2021-04-13 2022-10-19 Universal Display Corporation Plasmonic oleds and vertical dipole emitters
EP4079742A1 (de) 2021-04-14 2022-10-26 Merck Patent GmbH Metallkomplexe
US20220352478A1 (en) 2021-04-14 2022-11-03 Universal Display Corporation Organic eletroluminescent materials and devices
US20220407020A1 (en) 2021-04-23 2022-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US20230006149A1 (en) 2021-04-23 2023-01-05 Universal Display Corporation Organic electroluminescent materials and devices
JP2024515366A (ja) 2021-04-23 2024-04-09 メルク パテント ゲーエムベーハー 有機機能材料の調合物
WO2022229126A1 (de) 2021-04-29 2022-11-03 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
KR20240005806A (ko) 2021-04-29 2024-01-12 메르크 파텐트 게엠베하 유기 전계발광 디바이스용 재료
EP4330257A1 (de) 2021-04-30 2024-03-06 Merck Patent GmbH Stickstoffhaltige, heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen
CN117355364A (zh) 2021-05-21 2024-01-05 默克专利有限公司 用于连续纯化至少一种功能材料的方法和用于连续纯化至少一种功能材料的装置
US20230133787A1 (en) 2021-06-08 2023-05-04 University Of Southern California Molecular Alignment of Homoleptic Iridium Phosphors
DE112022003409A5 (de) 2021-07-06 2024-05-23 MERCK Patent Gesellschaft mit beschränkter Haftung Materialien für organische elektrolumineszenzvorrichtungen
CN117730638A (zh) 2021-08-02 2024-03-19 默克专利有限公司 通过组合油墨进行的印刷方法
EP4402221A1 (de) 2021-09-14 2024-07-24 Merck Patent GmbH Borhaltige, heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen
EP4151699A1 (en) 2021-09-17 2023-03-22 Universal Display Corporation Organic electroluminescent materials and devices
EP4410071A1 (de) 2021-09-28 2024-08-07 Merck Patent GmbH Materialien für elektronische vorrichtungen
DE112022004658A5 (de) 2021-09-28 2024-07-25 Merck Patent Gmbh Materialien für elektronische vorrichtungen
WO2023052313A1 (de) 2021-09-28 2023-04-06 Merck Patent Gmbh Materialien für elektronische vorrichtungen
CN118056486A (zh) 2021-09-28 2024-05-17 默克专利有限公司 用于电子器件的材料
TW202349760A (zh) 2021-10-05 2023-12-16 德商麥克專利有限公司 電子裝置之有機元件的形成方法
EP4423209A1 (de) 2021-10-27 2024-09-04 Merck Patent GmbH Bor- und stickstoffhaltige, heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen
WO2023094412A1 (de) 2021-11-25 2023-06-01 Merck Patent Gmbh Materialien für elektronische vorrichtungen
EP4442093A1 (en) 2021-11-30 2024-10-09 Merck Patent GmbH Compounds having fluorene structures
CN118401524A (zh) 2021-12-13 2024-07-26 默克专利有限公司 用于有机电致发光器件的材料
US20240343970A1 (en) 2021-12-16 2024-10-17 Universal Display Corporation Organic electroluminescent materials and devices
KR20240123834A (ko) 2021-12-21 2024-08-14 메르크 파텐트 게엠베하 전자 디바이스
WO2023117837A1 (de) 2021-12-21 2023-06-29 Merck Patent Gmbh Verfahren zur herstellung von deuterierten organischen verbindungen
KR20240127395A (ko) 2021-12-21 2024-08-22 메르크 파텐트 게엠베하 전자 디바이스
TW202340423A (zh) 2022-01-20 2023-10-16 德商麥克專利有限公司 具有混合主體系統之有機電元件
KR20240146680A (ko) 2022-02-09 2024-10-08 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 재료
CN118647604A (zh) 2022-02-14 2024-09-13 默克专利有限公司 用于电子器件的材料
WO2023161168A1 (de) 2022-02-23 2023-08-31 Merck Patent Gmbh Aromatische heterocyclen für organische elektrolumineszenzvorrichtungen
CN118696106A (zh) 2022-02-23 2024-09-24 默克专利有限公司 用于有机电致发光器件的含氮杂环化合物
US20230292592A1 (en) 2022-03-09 2023-09-14 Universal Display Corporation Organic electroluminescent materials and devices
US20230337516A1 (en) 2022-04-18 2023-10-19 Universal Display Corporation Organic electroluminescent materials and devices
WO2023213837A1 (de) 2022-05-06 2023-11-09 Merck Patent Gmbh Cyclische verbindungen für organische elektrolumineszenzvorrichtungen
WO2023222559A1 (de) 2022-05-18 2023-11-23 Merck Patent Gmbh Verfahren zur herstellung von deuterierten organischen verbindungen
US20230389421A1 (en) 2022-05-24 2023-11-30 Universal Display Corporation Organic electroluminescent materials and devices
TW202411366A (zh) 2022-06-07 2024-03-16 德商麥克專利有限公司 藉由組合油墨來印刷電子裝置功能層之方法
EP4293001A1 (en) 2022-06-08 2023-12-20 Universal Display Corporation Organic electroluminescent materials and devices
WO2023247345A1 (de) 2022-06-20 2023-12-28 Merck Patent Gmbh Heterocyclen für photoelektrische vorrichtungen
WO2023247338A1 (de) 2022-06-20 2023-12-28 Merck Patent Gmbh Organische heterocyclen für photoelektrische vorrichtungen
US20240016051A1 (en) 2022-06-28 2024-01-11 Universal Display Corporation Organic electroluminescent materials and devices
WO2024013004A1 (de) 2022-07-11 2024-01-18 Merck Patent Gmbh Materialien für elektronische vorrichtungen
EP4311849A1 (en) 2022-07-27 2024-01-31 UDC Ireland Limited Metal complexes
US20240107880A1 (en) 2022-08-17 2024-03-28 Universal Display Corporation Organic electroluminescent materials and devices
WO2024061942A1 (de) 2022-09-22 2024-03-28 Merck Patent Gmbh Stickstoffenthaltende verbindungen für organische elektrolumineszenzvorrichtungen
WO2024061948A1 (de) 2022-09-22 2024-03-28 Merck Patent Gmbh Stickstoffenthaltende heterocyclen für organische elektrolumineszenzvorrichtungen
US20240196730A1 (en) 2022-10-27 2024-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US20240188319A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US20240188316A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US20240188419A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US20240180025A1 (en) 2022-10-27 2024-05-30 Universal Display Corporation Organic electroluminescent materials and devices
WO2024094592A2 (de) 2022-11-01 2024-05-10 Merck Patent Gmbh Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen
WO2024105066A1 (en) 2022-11-17 2024-05-23 Merck Patent Gmbh Materials for organic electroluminescent devices
US20240247017A1 (en) 2022-12-14 2024-07-25 Universal Display Corporation Organic electroluminescent materials and devices
WO2024126635A1 (en) 2022-12-16 2024-06-20 Merck Patent Gmbh Formulation of an organic functional material
WO2024132993A1 (de) 2022-12-19 2024-06-27 Merck Patent Gmbh Materialien für elektronische vorrichtungen
WO2024133048A1 (en) 2022-12-20 2024-06-27 Merck Patent Gmbh Method for preparing deuterated aromatic compounds
WO2024149694A1 (de) 2023-01-10 2024-07-18 Merck Patent Gmbh Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen
WO2024153568A1 (de) 2023-01-17 2024-07-25 Merck Patent Gmbh Heterocyclen für organische elektrolumineszenzvorrichtungen
WO2024170605A1 (en) 2023-02-17 2024-08-22 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2024184050A1 (de) 2023-03-07 2024-09-12 Merck Patent Gmbh Cyclische stickstoffverbindungen für organische elektrolumineszenzvorrichtungen
WO2024194264A1 (de) 2023-03-20 2024-09-26 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
WO2024218109A1 (de) 2023-04-20 2024-10-24 Merck Patent Gmbh Materialien für elektronische vorrichtungen

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0906948A1 (en) * 1997-10-02 1999-04-07 Xerox Corporation Electroluminescent devices

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5942340A (en) * 1997-10-02 1999-08-24 Xerox Corporation Indolocarbazole electroluminescent devices
JP3924868B2 (ja) * 1997-11-05 2007-06-06 東レ株式会社 有機積層薄膜発光素子
US7001536B2 (en) 1999-03-23 2006-02-21 The Trustees Of Princeton University Organometallic complexes as phosphorescent emitters in organic LEDs
EP2278637B2 (en) * 1999-12-01 2021-06-09 The Trustees of Princeton University Complexes of form L2MX
JP4068279B2 (ja) * 2000-02-23 2008-03-26 パイオニア株式会社 有機エレクトロルミネッセンス素子
US6614175B2 (en) * 2001-01-26 2003-09-02 Xerox Corporation Organic light emitting devices
JP2002305083A (ja) 2001-04-04 2002-10-18 Mitsubishi Chemicals Corp 有機電界発光素子
JP2002352957A (ja) 2001-05-23 2002-12-06 Honda Motor Co Ltd 有機エレクトロルミネッセンス素子
US20030205696A1 (en) * 2002-04-25 2003-11-06 Canon Kabushiki Kaisha Carbazole-based materials for guest-host electroluminescent systems
US6670054B1 (en) * 2002-07-25 2003-12-30 Xerox Corporation Electroluminescent devices
KR100695106B1 (ko) * 2002-12-24 2007-03-14 삼성에스디아이 주식회사 청색 발광 고분자 및 이를 채용한 유기 전계 발광 소자
JP4630637B2 (ja) 2003-11-21 2011-02-09 キヤノン株式会社 有機発光素子及び有機化合物
JP2005213188A (ja) 2004-01-29 2005-08-11 Mitsubishi Chemicals Corp 化合物、電荷輸送材料、有機電界発光素子材料および有機電界発光素子
JP5040070B2 (ja) 2004-05-25 2012-10-03 三菱化学株式会社 電荷輸送材料、積層体及び有機電界発光素子
US7402681B2 (en) * 2004-12-14 2008-07-22 Xerox Corporation Compound with indolocarbazole moieties and devices containing such compound
WO2006033538A1 (en) 2004-09-20 2006-03-30 Lg Chem. Ltd. Carbazole derivative and organic light emitting device using same
KR20080085000A (ko) 2005-12-01 2008-09-22 신닛테츠가가쿠 가부시키가이샤 유기 전계 발광소자
CN102633820B (zh) 2005-12-01 2015-01-21 新日铁住金化学株式会社 有机电致发光元件用化合物及有机电致发光元件
WO2008056746A1 (fr) 2006-11-09 2008-05-15 Nippon Steel Chemical Co., Ltd. Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0906948A1 (en) * 1997-10-02 1999-04-07 Xerox Corporation Electroluminescent devices

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JP特开2004-204234A 2004.07.22 *
JP特表2003-515897A 2003.05.07 *

Also Published As

Publication number Publication date
US7993760B2 (en) 2011-08-09
TWI378099B (zh) 2012-12-01
EP1956022A1 (en) 2008-08-13
CN102633820A (zh) 2012-08-15
KR101082258B1 (ko) 2011-11-09
US20090302742A1 (en) 2009-12-10
EP1956022B1 (en) 2012-07-25
TW200734340A (en) 2007-09-16
JP4593631B2 (ja) 2010-12-08
EP1956022A4 (en) 2011-07-13
JPWO2007063754A1 (ja) 2009-05-07
KR20080085001A (ko) 2008-09-22
CN101321755B (zh) 2012-04-18
CN101321755A (zh) 2008-12-10
WO2007063754A1 (ja) 2007-06-07

Similar Documents

Publication Publication Date Title
CN102633820B (zh) 有机电致发光元件用化合物及有机电致发光元件
CN101511834B (zh) 有机场致发光元件用化合物及有机场致发光元件
EP2565249B1 (en) Cyclometallated tetradentate Pt (II) complexes
CN102754237B (zh) 有机电致发光元件
KR101005160B1 (ko) 유기 전계 발광 소자용 화합물 및 유기 전계 발광 소자
CN102939674B (zh) 有机场致发光元件
CN101233127B (zh) 杂环化合物及使用它的有机电致发光元件
TWI518071B (zh) Organic light field components
EP2415772B1 (en) Material for use in phosphorescent device and organic electroluminescent device using same
CN107793437B (zh) 3配位铜(i)-卡宾配合物
TWI438195B (zh) A compound for an organic electroluminescent device, and an organic electroluminescent device using the same
TWI466980B (zh) Organic electroluminescent elements
CN102282695B (zh) 有机电致发光元件
WO2009136586A1 (ja) 有機電界発光素子用化合物及び有機電界発光素子
EP2075310B1 (en) Organic electroluminescent device material and organic electroluminescent device
CN101959857B (zh) 有机场致发光元件用化合物及使用其的有机场致发光元件
WO2012108881A1 (en) Organic light emitting device and materials for use in same
CN101939296A (zh) 磷光发光二极管中的含咔唑材料
CN101371377A (zh) 有机场致发光元件
WO2005089025A1 (ja) 有機電界発光素子
KR20120131151A (ko) 유기금속성 착체를 기초로 한 이온쌍 형성 연질 염 및 유기 발광 다이오드에서의 상기 염의 용도
CN103159745A (zh) 用于有机电激发光装置的化合物及有机电激发光装置
KR20240110118A (ko) 신규한 유기 금속 화합물 및 이를 포함하는 유기발광소자
KR20140083413A (ko) 적색 인광 화합물 및 이를 이용한 유기전계발광소자

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C53 Correction of patent of invention or patent application
CB02 Change of applicant information

Address after: Tokyo, Japan

Applicant after: Nippon Steel Chemical Co.

Address before: Tokyo, Japan

Applicant before: Nippon Seel Chemical Co., Ltd.

COR Change of bibliographic data

Free format text: CORRECT: APPLICANT; FROM: NIPPON SEEL CHEMICAL CO., LTD. TO: NIPPON STEEL + SUMITOMO METAL CORPORATION

C14 Grant of patent or utility model
GR01 Patent grant
TR01 Transfer of patent right

Effective date of registration: 20191210

Address after: No.13-1, No.1, No.1, No

Patentee after: Nippon Iron Chemical Materials Co., Ltd.

Address before: Tokyo, Japan

Patentee before: Nippon Steel Chemical Co.

TR01 Transfer of patent right