TWI391396B - 環化金屬之咪唑并〔1,2-f〕啡啶及二咪唑〔1,2-a:1’,2’-c〕喹唑啉配位體的金屬錯合物、與其等電子及苯基化類似物 - Google Patents
環化金屬之咪唑并〔1,2-f〕啡啶及二咪唑〔1,2-a:1’,2’-c〕喹唑啉配位體的金屬錯合物、與其等電子及苯基化類似物 Download PDFInfo
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- TWI391396B TWI391396B TW096104920A TW96104920A TWI391396B TW I391396 B TWI391396 B TW I391396B TW 096104920 A TW096104920 A TW 096104920A TW 96104920 A TW96104920 A TW 96104920A TW I391396 B TWI391396 B TW I391396B
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- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
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- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 16
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- 229940125898 compound 5 Drugs 0.000 description 1
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- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- GELVFUZODOGHGL-UHFFFAOYSA-N ethyl n-[2-(2-methylphenyl)phenyl]carbamate Chemical group CCOC(=O)NC1=CC=CC=C1C1=CC=CC=C1C GELVFUZODOGHGL-UHFFFAOYSA-N 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 1
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- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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Description
大體言之本發明係關於有機發光裝置(OLED)及用於此等裝置中之有機化合物。
使用有機材料之光電裝置因許多原因而變得日益理想。由於許多用於製造該等裝置之材料相對廉價,因此有機光電裝置與無機裝置相比具有成本優勢之潛力。另外,有機材料之固有性質(諸如其可撓性)可使其良好適用於特定應用,諸如製造於可撓性基板上。有機光電裝置之實例包括有機發光裝置(OLED)、有機光電晶體、有機光電池及有機光偵測器。對於OLED而言,有機材料與習知材料相比可具有效能優勢。舉例而言,一般有機發射層之發光波長可易於以適當摻雜劑調整。
如本文所用之術語"有機"包括可用於製造有機光電裝置之聚合材料以及小分子有機材料。"小分子"係指非聚合物之任何有機材料且"小分子"實際上可相當大。在某些情況下,小分子可包括重複單元。舉例而言,使用長鏈烷基作為取代基並不將分子自"小分子"類別中移除。小分子亦可(例如)作為聚合物主鏈上之側基或作為主鏈之部分併入聚合物中。小分子亦可充當樹狀體之核心部分,該樹狀體由一系列建立在核心部分上之化學外殼組成。樹狀體之核心部分可為螢光或磷光小分子發射體。樹狀體可為"小分子",且據信目前用於OLED領域之所有樹狀體均為小分子。一般而言,小分子具有精確定義之化學式及單一分子量,而聚合物具有不同分子間不同之化學式及分子量。如本文所用之術語"有機"包括烴基及經雜原子取代之烴基配位體之金屬錯合物。
OLED使用當穿過裝置施加電壓時發光之有機薄膜。OLED成為用於(諸如)平板顯示器、照明及背光之應用中之日益令人關注的技術。美國專利第5,844,363號、第6,303,238號及第5,707,745號中描述了數種OLED材料及組態,該等專利以全文引用的方式併入本文中。
OLED裝置一般(但並非始終)預期經由至少一電極發光,且有機光電裝置中可使用一或多個透明電極。舉例而言,可使用透明電極材料(諸如氧化銦錫(ITO))作為底電極。亦可使用(諸如)揭示於美國專利第5,703,436號及第5,707,745號中之透明頂電極,該等專利以全文引用的方式合併入本文中。對於預期僅經由底電極發光之裝置而言,頂電極不需要為透明的,且可包含具有高電導率之厚的反射金屬層。類似地,對於預期僅經由頂電極發光之裝置而言,底電極可為不透明及/或反射性。當電極不需要為透明時,使用較厚之層可提供較佳電導率且使用反射電極可藉由將光反射回透明電極而增加經由另一電極發光之量。亦可製造完全透明之裝置,其中兩電極均為透明的。亦可製造側面發射OLED,且該等裝置中一或兩個電極可為不透明或反射性的。
如本文所用之"頂部"意謂最遠離基板,而"底部"意謂最接近基板。舉例而言,對於具有兩電極之裝置而言,底電極為最接近基板之電極且一般為首先製造之電極。底電極具有兩個表面,最接近基板之下表面及較遠離基板之上表面。當第一層描述為"安置於"第二層"上"時,該第一層係安置成較遠離基板。除非特定說明第一層為與第二層"實體接觸",否則在第一層與第二層之間可存在其他層。舉例而言,可描述成陰極"安置於"陽極"上",但其間可存在各種有機層。
如本文所用之"溶液可處理性"意謂能以溶液或懸浮液形式在液體介質中溶解、分散或傳遞及/或自液體介質沈積。
如本文所用且如熟習此項技術者通常所瞭解,若第一能級接近真空能級,則第一"最高佔用分子軌道"(HOMO)或"最低未佔用分子軌道"(LUMO)能級"大於"或"高於"第二HOMO或LUMO能級。由於游離電位(IP)相對於真空能級量測為負能量,因此較高HOMO能級對應於具有較小絕對值之IP(負值較小之IP)。類似地,較高LUMO能級對應於具有較小絕對值之電子親和力(EA)(負值較小之EA)。在習知能級表上,真空能級處於頂端,材料之LUMO能級高於相同材料之HOMO能級。"較高"HOMO能級或LUMO能級比"較低"HOMO能級或LUMO能級更接近該表之頂端。
長壽命藍光發射磷光摻雜劑之研發被視為目前OLED研究及發展之關鍵卻未實現之目標。隨著已展示發射峰位於深藍或近UV區之磷光OLED裝置,顯示100尼特初始亮度之藍光發射裝置之壽命已達到約數百小時(其中"壽命"係指在恆定電流下,亮度下降至初始水平之50%之時間)。舉例而言,可使用衍生自N-甲基-2-苯基咪唑之雙牙配位體之銥(III)錯合物製備藍色OLED裝置,但使用此等摻雜劑觀察到極短之壽命(在100尼特初始發光下約250小時)。
由於預期大部分商業應用要求在200尼特初始發光下超過10,000小時之壽命,因此欲尋求藍色磷光OLED裝置壽命之重要改良。
依照上述目標,本文描述數種新穎類別之磷光金屬錯合物及OLED裝置,其包含環化金屬之咪唑并[1,2-f]啡啶或二咪唑[1,2-a:1',2'-c]喹唑啉配位體或其等電子或苯基化類似物,該等物質可用於製備長壽命有效之藍光、綠光及紅光發射OLED裝置。許多此等錯合物具有對於該等高共軛分子而言令人驚奇較窄的磷光發射線形或令人驚奇較高的三重態能量,或同時具有兩者。使用G98/B31yp/cep-31g基底函數組進行密度泛函數理論(DFT)計算表明許多本發明之藍光發射錯合物具有相對較小之單態-三重態能隙(小於約0.25 eV)。不希望受限於理論,本發明者認為稠環之18π電子計數及特定排列與較小單態-三重態能帶隙相關且可對光譜線形及裝置壽命產生有益作用。較小單態-三重態能隙亦可促進低電壓OLED裝置之設計且有益降低包含該等化合物之OLED裝置之功率消耗。
大體而言,OLED包含至少一個安置於陽極與陰極之間且與其電連接之有機層。當施加電流時,陽極向有機層向有機層注入電洞且陰極向有機層注入電子。經注入之電洞及電子各向帶有相反電荷之電極遷移。當電子及電洞位於相同分子上時,形成具有激發能態之定域電子-電洞對,"激子"。當激子經由光電發射機制弛豫時發光。在某些情況下,激子可定域於準分子或激發複合物體上。亦可存在非輻射機制(諸如熱弛豫),但一般認為是不理想的。
如(例如)美國專利第4,769,292號(其以全文引用的方式併入本文中)中所揭示,最初之OLED使用自其單態發光("螢光")之發射分子。螢光發射一般發生在小於10奈秒之時段內。
最近已展示具有自其三重態發光("磷光")之發射材料之OLED。Baldo等人,"Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,"Nature,第395卷,151-154,1998;("Baldo-I")及Baldo等人,"Very high-efficiency green organic light-emitting devices based on electrophosphorescence,"Appl.Phys.Lett.,第75卷,第3期,4-6(1999)("Baldo-II"),其以全文引用的方式併入本文中。磷光可稱為"禁戒"躍遷,因為躍遷需要自旋態之變化,且量子力學指示該躍遷並非有利的。因此,磷光一般發生在超過至少10奈秒且通常大於100奈秒之時段內。若磷光之自然輻射壽命過長,則三重態可因非輻射機制而衰變使得不再發光。亦通常在極低溫度下在含有具有未共用電子對之雜原子的分子中觀察到有機磷光。該分子為2,2'-聯吡啶。非輻射衰變機制通常具有溫度相關性,使得在液氮溫度下展現磷光之有機材料通常在室溫下不展現出磷光。但如由Baldo所示,此問題可藉由選擇在室溫下發出磷光之磷光化合物來解決。代表性發射層包括(諸如)揭示於美國專利第6,303,238號、第6,310,360號、第6,830,828號及第6,835,469號;美國專利申請公開案第2002-0182441號及WO-02/074015中之摻雜或未摻雜磷光有機金屬材料。
大體而言,據信OLED中之激子係以約3:1之比例(亦即約75%三重態及25%單態)產生。參見Adachi等人,"Nearly 100% Internal Phosphorescent Efficiency In An Organic Light Emitting Device,"J.Appl.Phys.,90,5048(2001),其以全文引用的方式併入本文中。在許多情況下,單態激子可易於經由"系統間穿越"將其能量轉移至三重激發態,而三重態激子不能輕易將其能量轉移至單態激發態。因此,理論上100%內部量子效率對於磷光OLED係可能的。在螢光裝置中,三重態激子之能量通常在加熱裝置之無輻射衰變過程中損失,從而產生遠遠較低之內部量子效率。使用自三重激發態發射之磷光材料之OLED揭示於(例如)美國專利第6,303,238號中,其以全文引用的方式併入本文中。
磷光之前可為自三重激發態向中間非三重態(自此發生發射衰變)之躍遷。舉例而言,與鑭系元素配位之有機分子通常自定域於鑭系金屬上之激發態發出磷光。然而,該等材料並非直接自三重激發態發出磷光而是自集中於鑭系金屬離子上之原子激發態發射。二酮酸銪錯合物表示此等類型物質中之一群。
可藉由約束(較佳經由鍵結)有機分子接近高原子序之原子而使來自三重態之磷光增強超過螢光。稱為重原子效應之此現象係由稱為自旋軌道耦合之機制產生。可自有機金屬分子(諸如參(2-苯基吡啶)銥(III))之激發金屬-配位體電荷轉移(MLCT)狀態觀察到該磷光躍遷。雖然不希望受限於理論,但據信有機金屬錯合物中之有機金屬-碳鍵為達成所需有機分子接近高原子序原子之尤其較佳之方法。特定言之,在本申請案之範圍中,有機金屬錯合物中存在有機碳-金屬鍵可促進更大之MLCT特徵,此特徵可用於製造高效裝置。
如本文所用之術語"三重態能量"係指對應於既定材料之磷光光譜中可辨別之最高能量特徵之能量。最高能量特徵不必為磷光光譜中具有最大強度之峰,且可(例如)為該峰之高能量側上清晰肩部之局部最大值。
如本文所用之術語"有機金屬"如熟習此項技術者通常所瞭解且如(例如)Gary L.Miessler及Donald A.Tarr之"Inorganic Chemistry"(第2版),Prentice Hall(1998)中所給出。因此,術語有機金屬係指具有經由碳-金屬鍵與金屬鍵結之有機基團的化合物。此類化合物本身不包括配位化合物,配位化合物為僅具有雜原子之供體鍵之物質,諸如胺、鹵化物、擬鹵化物(CN等)之金屬錯合物及其類似物。實際上有機金屬化合物除一或多個與有機物質形成之碳-金屬鍵之外可包含一或多個雜原子之供體鍵。與有機物質形成之碳-金屬鍵係指金屬與有機基團(諸如苯基、烷基、烯基等)之碳原子之間的直接鍵,而並非指與"無機碳"(諸如CN或CO之碳)形成之金屬鍵。
圖1展示有機發光裝置100。圖示並非必須按比例繪製。裝置100可包括基板110、陽極115、電洞注入層120、電洞傳遞層125、電子阻擋層130、發射層135、電洞阻擋層140、電子傳遞層145、電子注入層150、保護層155及陰極160。陰極160為具有第一導電層162及第二導電層164之複合陰極。可藉由依序沈積所述層製造裝置100。
基板110可為提供所需結構性質之任何合適基板。基板110可為可撓性或硬質。基板110可為透明、半透明或不透明。塑料及玻璃為較佳硬質基板材料之實例。塑料及金屬箔片為較佳可撓性基板材料之實例。基板110可為半導體材料以有利於電路之製造。舉例而言,基板110可為電路在其上製造,能夠控制隨後沈積於基板上之OLED之矽晶圓。可使用其他基板。可對基板110之材料及厚度進行選擇以獲得所需結構及光學性質。
陽極115可為導電性足以將電洞傳遞至有機層之任何合適之陽極。陽極115之材料較佳具有高於約4 eV之功函數("高功函數材料")。較佳陽極材料包括導電金屬氧化物(諸如氧化銦錫(ITO)及氧化銦鋅(IZO)、氧化鋁鋅(AlZnO))及金屬。陽極115(及基板110)可足夠透明以產生底部發射裝置。較佳透明基板及陽極組合為沈積於玻璃或塑料(基板)上之市售ITO(陽極)。可撓性及透明基板-陽極組合揭示於美國專利第5,844,363號及第6,602,540 B2號中,該等專利以全文引用的方式併入本文中。陽極115可為不透明及/或反射性。反射性陽極115可較佳用於某些頂部發射裝置以增加裝置頂部發光之量。可對陽極115之材料及厚度進行選擇以獲得所需導電性質及光學性質。當陽極115為透明時,對於足夠厚以提供所需電導率但足夠薄以提供所需透明度之特定材料而言可存在一定厚度範圍。可使用其他陽極材料及結構。
電洞傳遞層125可包括能夠傳遞電洞之材料。電洞傳遞層130可為本質(未摻雜)或摻雜電洞傳遞層。可使用摻雜增強電導率。α-NPD及TPD為本質電洞傳遞層之實例。P型摻雜電洞傳遞層之實例為如頒予Forrest等人之美國專利申請公開案第2003-0230980號中(其以全文引用的方式併入本文中)所揭示之以50:1之莫耳比摻雜F4-TCNQ之m-MTDATA。可使用其他電洞傳遞層。
發射層135可包括當電流穿過陽極115與陰極160之間時能夠發光之有機材料。儘管亦可使用螢光發射材料,但發射層135較佳含有磷光發射材料。磷光材料因與該等材料相關之較高發光效率而較佳。發射層135亦可包含能夠傳遞電子及/或電洞,摻雜發射材料之主體材料,該發射材料可截獲電子、電洞及/或激子使得激子經由光電發射機制自發射材料弛豫。發射層135可包含組合傳遞性質與發射性質之單一材料。無論發射材料為摻雜劑還是主要成份,發射層135皆可包含其他材料,諸如調整發射材料之發射之摻雜劑。發射層135可包括複數種能夠組合發射所需光譜之發射材料。磷光發射材料之實例包括Ir(ppy)3
。螢光發射材料之實例包括DCM及DMQA。主體材料之實例包括Alq3
、CBP及mCP。發射材料及主體材料之實例揭示於頒予Thompson等人之美國專利第6,303,238號中,其以全文引用的方式併入本文中。發射材料可以許多方式包括於發射層135中。舉例而言,可將發射小分子併入聚合物中。可藉由數種方式完成此操作:藉由將小分子作為獨立且分離之分子物質摻雜至聚合物中;或藉由將小分子併入聚合物之主鏈中以形成共聚物;或藉由將小分子作為聚合物上之側基鍵結。可使用其他發射層材料及結構。舉例而言,小分子發射材料可作為樹狀體之核心存在。
許多可用之發射材料包括一或多個與金屬中心鍵結之配位體。若配位體直接向有機金屬發射材料貢獻光敏性質,則可將其稱為"光敏性"配位體。"光敏性"配位體與金屬結合可提供當發射光子時電子移動之最低及最高能級。其他配位體可稱為"輔助"配位體。輔助配位體可(例如)藉由使光敏性配位體之能級位移而改變分子之光敏性質,但輔助配位體不直接提供與發光相關之能級。在一分子中為光敏性之配位體在另一分子中可能為輔助性。光敏性及輔助性之此等定義意欲作為非限制性理論。
電子傳遞層145可包括能夠傳遞電子之材料。電子傳遞層145可為本質(未摻雜)或摻雜電子傳遞層。可使用摻雜增強電導率。Alq3
為本質電子傳遞層之實例。N型摻雜電子傳遞層之實例為如頒予Forrest等人之美國專利申請公開案第2003-0230980號中(其以全文引用的方式併入本文中)所揭示之以1:1之莫耳比摻雜Li之BPhen。可使用其他電子傳遞層。
可對電子傳遞層之載荷組份進行選擇使得可將電子有效自陰極注入電子傳遞層之LUMO(最低未佔用分子軌道)能級。"載荷組份"為負責實際上傳遞電子之LUMO能級之材料。此組份可為基礎材料或其可為摻雜劑。有機材料之LUMO能級一般可由該材料之電子親和力表徵且陰極之相對電子注入效率一般可根據陰極材料之功函數表徵。此意謂電子傳遞層及鄰近陰極之較佳性質可根據ETL載荷組份之電子親和力及陰極材料之功函數來規定。特定言之,為達成高電子注入效率,陰極材料之功函數較佳超過電子傳遞層載荷組份之電子親和力不大於約0.75 eV,更佳不大於約0.5 eV。類似條件適用於電子注入之任何層。
陰極160可為此項技術中已知之使得陰極160能夠傳導電子且將其注入裝置100之有機層之任何合適材料或材料組合。陰極160可為透明或不透明,且可為反射性。金屬及金屬氧化物為合適陰極材料之實例。陰極160可為單層或可具有複合結構。圖1展示具有薄金屬層162及較厚導電金屬氧化物層164之複合陰極160。在複合陰極中,用於較厚層164之較佳材料包括ITO、IZO及其他此項技術中已知之材料。美國專利第5,703,436號、第5,707,745號、第6,548,956 B2號及第6,576,134 B2號(該等專利以全文引用的方式併入本文中)揭示了陰極之實例,包括具有諸如Mg:Ag之金屬薄層及上覆透明導電濺鍍沈積ITO層之複合陰極。與下伏有機層接觸之陰極160之部分(無論其為單層陰極160、複合陰極之薄金屬層162還是某其他部分)較佳由功函數低於約4 eV之材料("低功函數材料")製成。可使用其他陰極材料及結構。
阻擋層可用於減少離開發射之層載荷子(電子或電洞)及/或激子之數目。電子阻擋層130可安置於發射層135與電洞傳遞層125之間以阻擋電子朝電洞傳遞層125之方向離開發射層135。類似地,電洞阻擋層140可安置於發射層135與電子傳遞層145之間以阻擋電洞朝電子傳遞層145之方向離開發射層135。阻擋層亦可用於阻擋激子擴散出發射層。阻擋層之理論及用途更詳細描述於美國專利第6,097,147號及頒予Forrest等人之美國專利申請公開案第2003-0230980號中,該等專利以全文引用的方式併入本文中。
如本文所用且如熟習此項技術者所瞭解,術語"阻擋層"意謂該層提供顯著抑制載荷子及/或激子傳遞穿過裝置之阻障,並非說明該層必須完全阻擋載荷子及/或激子。與無阻擋層之類似裝置相比,裝置中存在該阻擋層可產生實質上較高之效率。而且,阻擋層可用於將發射限制於OLED之所需區域。
大體而言,注入層包含可改良將載荷子自一層(諸如電極或有機層)注入鄰近有機層之材料。注入層亦可執行電荷傳遞功能。在裝置100中,電洞注入層120可為改良將電洞自陽極115注入電洞傳遞層125之任何層。CuPc為可用作自ITO陽極115及其他陽極注入之電洞注入層之材料的實例。在裝置100中,電子注入層150可為改良將電子注入電子傳遞層145之任何層。LiF/Al為可用作自鄰近層注入電子傳遞層之電子注入層之材料的實例。對於注入層可使用其他材料或材料組合。視特定裝置之組態而定,注入層以不同於裝置100中所示之位置安置。注入層之更多實例提供於頒予Lu等人之美國專利申請案第09/931,948號中,其以全文引用的方式併入本文中。電洞注入層可包含溶液沈積材料(諸如旋塗聚合物,例如PEDOT:PSS)或其可為蒸氣沈積小分子材料(例如CuPc或MTDATA)。
電洞注入層(HIL)可平面化或濕潤陽極表面以便提供將電洞自陽極有效注入電洞注入材料。電洞注入層亦可具有載荷組份,該載荷組份具有如由其本文所述相對游離電位(IP)能量所定義有利與HIL一側上之鄰近陽極層及HIL相對側上之電洞傳遞層相配之HOMO(最高佔用分子軌道)能級。"載荷組份"為負責實際上傳遞電洞之HOMO能級之材料。此組份可為HIL之基礎材料或其可為摻雜劑。使用摻雜HIL允許根據摻雜劑之電學性質對其進行選擇,且根據形態性質(諸如濕潤、可撓性、韌性等)選擇主體。HIL材料之較佳性質為可將電洞自陽極有效注入HIL材料之性質。特定言之,HIL之載荷組份較佳具有超過陽極材料之IP不大於約0.7 eV之IP。載荷組份更佳具有超過陽極材料不大於約0.5 eV之IP。類似條件適用於電洞注入之任何層。HIL材料與通常用於OLED之電洞傳遞層中之習知電洞傳遞材料的另外不同之處在於該等HIL材料之電洞電導率實質上小於習知電洞傳遞材料之電洞電導率。本發明HIL之厚度可足夠厚以有助於平面化或濕潤陽極層之表面。舉例而言,對於極平滑之陽極表面而言小至10 nm之HIL厚度可接受。然而,由於陽極表面傾向於極為粗糙,因此在某些情況下高達50 nm之HIL厚度可為理想的。
保護層可用於在後續製造過程期間保護下伏層。舉例而言,用於製造金屬或金屬氧化物頂電極之過程可能損壞有機層且保護層可用於減少或消除此損壞。在裝置100中,保護層155可減少在製造陰極160期間對下伏有機層之損壞。較佳保護層對其傳遞之載流子類型(裝置100中之電子)具有高載流子遷移率,使得其不會顯著增加裝置100之操作電壓。CuPc、BCP及各種金屬酞菁為可用於保護層中之材料之實例。可使用其他材料或材料組合。保護層155之厚度較佳足夠厚使得存在極少或不存在由於有機保護層160沈積之後進行之製造過程對下伏層之損壞,但厚至顯著增加裝置100之操作電壓。保護層155可經摻雜以增加其電導率。舉例而言,CuPc或BCP保護層160可摻雜Li。保護層更詳細之描述可見於頒予Lu等人之美國專利申請案第09/931,948號中,其以全文以引用的方式併入本文中。
圖2展示反向OLED 200。該裝置包括基板210、陰極215、發射層220、電洞傳遞層225及陽極230。可藉由依序沈積所述層製造裝置200。由於最常用之OLED組態具有安置於陽極上之陰極,而裝置200具有安置於陽極230下之陰極215,因此可將裝置200稱為"反向"OLED。類似於相關於裝置100所描述之材料可用於裝置200之相應層中。圖2提供裝置100之結構可如何省略一些層之一實例。
圖1及圖2中所說明之簡單分層結構作為非限制性實例提供,且當然本發明之實施例可以各種其他結構使用。所述之特定材料及結構本質上為例示性的,且可使用其他材料及結構。藉由以不同方式組合所述之各種層可獲得功能OLED,或可基於設計、效能及成本因素完全將層省略。亦可包括其他未特定描述之層。可使用除特定描述之材料之外的材料。儘管許多本文提供之實例描述各種層包含單一材料,但當然亦可使用材料之組合,諸如主體材料與摻雜劑之混合物或更一般而言為混合物。而且,該等層可具有各種子層。本文給予各種層之名稱不意欲具有嚴格限制性。舉例而言,在裝置200中,電洞傳遞層225向發射層220傳遞電洞及注入電洞,且可描述為電洞傳遞層或電洞注入層。在一實施例中,OLED可描述為具有安置於陰極與陽極之間的"有機層"。此有機層可包含單一層或可進一步包含如(例如)相關於圖1及圖2所描述之多層不同有機材料。
亦可使用未特定描述之結構及材料,諸如揭示於(諸如)頒予Friend等人之美國專利第5,247,190號(其以全文引用的方式併入本文中)之包含聚合材料之OLED(PLED)。作為其他實施例,可使用具有單一有機層之OLED。舉例而言,如頒予Forrest等人之美國專利第5,707,745號(其以全文引用的方式併入本文中)所述,OLED可經堆疊。該OLED結構可不同於圖1及圖2中所說明之簡單分層結構。舉例而言,基板可包括成角反射表面以改良外部耦合,諸如頒予Forrest等人之美國專利第6,091,195號中所述之凸起結構及/或頒予Bulovic等人之美國專利第5,834,893號中所述之凹陷結構,該等專利以全文引用的方式併入本文中。
除非另有特定說明,否則各種實施例之層之任一者可由任何合適之方法沈積。對於有機層而言,較佳方法包括(諸如)描述於美國專利第6,013,982號及第6,087,196號中(其以全文引用的方式併入本文中)之熱蒸鍍、噴墨;(諸如)描述於頒予Forrest等人之美國專利第6,337,102號中(其以全文引用的方式併入本文中)之有機氣相沈積(OVPD);及(諸如)描述於美國專利申請案第10/233,470號中(其以全文引用的方式併入本文中)之有機蒸氣噴射印刷沈積(OVJP)。其他合適之沈積方法包括旋塗及其他基於溶液之方法。基於溶液之方法較佳在氮氣或惰性氣氛下進行。對於其他層而言,較佳方法包括熱蒸鍍。較佳圖案化方法包括(諸如)描述於美國專利第6,294,398號及第6,468,819號中(其以全文引用的方式併入本文中)之經遮罩沈積、冷焊;及與某些沈積方法(諸如噴墨及OVJD)相關之圖案化。亦可使用其他方法。可將待沈積之材料改質以使其與特定沈積方法相容。舉例而言,可在小分子中使用支鏈或未分枝且較佳含有至少3個碳之取代基(諸如烷基及芳基)以增強其經歷溶液處理之能力。可使用具有20個或20個以上碳之取代基,且3-20個碳為較佳範圍。由於不對稱材料可具有較低再結晶之傾向,因此與具有對稱結構之材料相比具有不對稱結構之材料之溶液處理性較佳。可使用樹狀體取代基增強小分子經歷溶液處理之能力。
可在不背離本發明之範疇之情況下以許多不同方式取代本文所揭示之分子。舉例而言,可將取代基添加至具有3個雙牙配位體之化合物,使得在添加取代基之後一或多個雙牙配位體連接在一起形成(例如)四牙配位體或六牙配位體。可形成其他該等鍵聯。由於此項技術中通常所瞭解之"螯合效應"之原因,據信相對於無鍵聯之類似化合物此類型之鍵聯可增加穩定性。
根據本發明之實施例製造之裝置可併入各種消費型產品中,包括平板顯示器、電腦螢幕、電視、廣告牌、室內或室外照明燈及/或信號燈、抬頭顯示器、完全透明顯示器、可撓性顯示器、雷射印表機、電話、行動電話、個人數位助理(PDA)、膝上型電腦、數位相機、可攜式攝影機、檢景器、微顯示器、車輛、大面積牆體、劇院或運動場螢幕或標誌牌。可使用各種控制機制來控制根據本發明製造之裝置,包括被動型矩陣及主動型矩陣。許多裝置意欲用於對於人類舒適之溫度範圍中,諸如18℃至30℃,且更佳在室溫下(20-25℃)。
本文所述之材料及結構可應用於除OLED之外的裝置中。舉例而言,其他光電裝置(諸如有機太陽能電池及有機光電偵測器)可使用該等材料及結構。更一般而言,有機裝置(諸如有機電晶體)可使用該等材料及結構。
術語"芳基"係指芳族碳環單價基團。除非另有特定說明,否則芳族碳環單價基團可經取代或未經取代。取代基可為F、烴基、經雜原子取代之烴基、氰基及其類似基團。
"烴基"意謂僅含有碳原子及氫原子之單價或二價直鏈、支鏈或環狀基團。單價烴基之實例包括下列基團:C1
-C20
烷基;經一或多個選自C1
-C20
烷基、C3
-C8
環烷基及芳基之基團取代之C1
-C20
烷基;C3
-C8
環烷基;經一或多個選自C1
-C20
烷基、C3
-C8
環烷基及芳基之基團取代之C3
-C8
環烷基;C6
-C18
芳基;及經一或多個選自C1
-C20
烷基、C3
-C8
環烷基及芳基之基團取代之C6
-C18
芳基。二價(橋接)烴基之實例包括:-CH2
-、-CH2
CH2
-、-CH2
CH2
CH2
-及1,2-伸苯基。
"雜原子"係指除碳或氫之外的原子。雜原子之實例包括氧、氮、磷、硫、硒、砷、氯、溴、矽及氟。
"雜芳基"係指芳族雜環單價基團。除非另有特定說明,否則芳族雜環單價基團可經取代或未經取代。取代基可為F、烴基、經雜原子取代之烴基、氰基及其類似基團。雜芳基之實例包括1-吡咯基、2-吡咯基、3-吡咯基、呋喃基、噻吩基、茚基、咪唑基、噁唑基、異噁唑基、咔唑基、噻唑基、嘧啶基、吡啶基、嗒嗪基、吡嗪基、苯并噻吩基及其類似基團及其經取代衍生物。
"鄰位"意謂芳基或雜芳基上鄰近第二環與第一環之連接點之位置。在經由1位連接之6員環芳基(諸如2,6-二甲苯基)之情況下,2位與6位為鄰位。在經由1位連接之5員環雜芳基(諸如2,5-二苯基吡咯-1-基)之情況下,2位與5位為鄰位。在本發明之範圍中,將鄰近連接點之碳處的環稠合(如2,3,4,5,7,8,9,10-八氫蒽-1-基中)視為鄰位取代的一種類型。
因此,在第一態樣中,本發明係關於一種包含磷光金屬錯合物之化合物,該錯合物包含選自組1之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;組1;
其中:E1a-q
係選自由C及N組成之群且共同包含18π電子系統;其限制條件為E1a
與E1p
不同;且R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成飽和或不飽和、芳族或非芳族環;其限制條件為當與N連接時,R1a-i
不為H。
在此第一態樣之第一較佳實施例中,該金屬係選自由Re、Ru、Os、Rh、Ir、Pd、Pt、Cu及Au組成之群,且該雙牙配位體係選自組2;甚至更佳為該雙牙配位體具有組2中之式gs1-1;組2; 組2,續;
其中:R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成飽和或不飽和、芳族或非芳族環。
在第二較佳實施例中,金屬為Ir或Pt,且雙牙配位體係選自組2。在第三較佳實施例中,金屬錯合物為選自組2之配位體之均配Ir錯合物。在第四較佳實施例中,金屬錯合物為混配Ir錯合物,其包含兩個選自組2之雙牙配位體及第三單陰離子雙牙配位體(較佳為乙醯丙酮根或經取代之乙醯丙酮根)。在第五較佳實施例中,金屬係選自由Re、Ru、Os、Rh、Ir、Pd、Pt、Cu及Au組成之群,且R1a-i
中之至少一者為2,6-二取代芳基。在第六較佳實施例中,金屬係選自由Ir及Pt組成之群,配位體具有式gs1-1,且R1b
為2,6-二取代芳基,較佳選自由以下基團組成之群:2,6-二甲苯基、2,4,6-三甲苯基、2,6-二異丙苯基、2,4,6-三異丙苯基、2,6-二異丙基-4-苯基苯基、2,6-二甲基-4-苯基苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二苯基苯基、2,6-二苯基-4-異丙苯基、2,4,6-三苯基苯基、2,6-二異丙基-4-(4-異丙苯基)、2,6-二異丙基-4-(3,5-二甲苯基)苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二異丙基-4-(吡啶-4-基)苯基及2,6-二-(3,5-二甲苯基)苯基。
在第二態樣中,本發明係關於一種選自組3之化合物,其中acac為乙醯丙酮根;組3; 組3,續; 組3,續; 組3,續; 組3,續; 組3,續;
在第三態樣中,本發明係關於一種包含第一態樣或第二態樣之化合物中之任一者之OLED裝置。
在第四態樣中,本發明係關於一種包含磷光金屬錯合物之化合物,該錯合物包含選自組4之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;組4;
其中:E1a-q
各自獨立選自由C及N組成之群且共同包含18π電子系統;其限制條件為E1a
與E1p
不同;且R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成飽和或不飽和、芳族或非芳族環;其限制條件為當與N連接時,R1a-i
不為H。
在此第四態樣之第一較佳實施例中,該雙牙配位體係選自組5;組5;
其中:R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或組5,續;
其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成環。
在此第四態樣之第二較佳實施例中,該雙牙配位體係選自組6;
其中:R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成環。
在第四態樣之第三較佳實施例中,該雙牙配位體經一或多個2,6-二取代芳基或雜芳基取代,該等取代基較佳選自由以下基團組成之群:2,6-二甲苯基、2,4,6-三甲苯基、2,6-二異丙苯基、2,4,6-三異丙苯基、2,6-二異丙基-4-苯基苯基、2,6-二甲基-4-苯基苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二苯基苯基、2,6-二苯基-4-異丙苯基、2,4,6-三苯基苯基、2,6-二異丙基-4-(4-異丙苯基)、2,6-二異丙基-4-(3,5-二甲苯基)苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二異丙基-4-(吡啶-4-基)苯基及2,6-二-(3,5-二甲苯基)苯基。
在第四態樣之第四較佳實施例中,該金屬係選自由Re、Ru、Os、Rh、Ir、Pd、Pt、Cu及Au組成之群,且較佳選自由Os、Ir及Pt組成之群,且最佳為Ir。
在第五態樣中,本發明係關於一種包含第四態樣之化合物之OLED裝置。
在第六態樣中,本發明係關於一種對應於第四態樣之配位體之化合物,其中金屬已由H置換。
在第七態樣中,本發明係關於一種包含磷光金屬錯合物之化合物,該錯合物包含選自組7之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體包含碳烯供體且可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;
其中:E1a-q
係選自由C及N組成之群且共同包含18π電子系統;其限制條件為E1a
與E1p
均為碳;且R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成飽和或不飽和、芳族或非芳族環;其限制條件為當與N連接時,R1a-i
不為H。
在此第七態樣之第一較佳實施例中,該化合物係選自組8;
其中:R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成飽和或不飽和、芳族或非芳族環;其限制條件為當與N連接時,R1a-i
不為H。
在第八態樣中,本發明係關於一種包含第七態樣之化合物之OLED裝置。
在第九態樣中,本發明係關於一種包含磷光金屬錯合物之化合物,該錯合物包含選自組9之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體包含碳烯供體且可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;組9;
其中:E1a-q
係選自由C及N組成之群且共同包含18π電子系統;其限制條件為E1a
與E1p
均為碳;且R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成飽和或不飽和、芳族或非芳族環;其限制條件為當與N連接時,R1a-i
不為H。
在此第九態樣之第一較佳實施例中,該化合物係選自組10;
其中:R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成飽和或不飽和、芳族或非芳族環;其限制條件為當與N連接時,R1a-i
不為H。
在第十態樣中,本發明係關於一種包含第九態樣之化合物之OLED裝置。
在第十一態樣中,本發明係關於一種包含磷光金屬錯合物之化合物,該錯合物包含選自組11之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;
其中:R1a-i
各自獨立為H、烴基、經雜原子取代之烴基、氰基、氟基、OR2a
、SR2a
、NR2a
R2b
、BR2a
R2b
或SiR2a
R2b
R2c
,其中R2a-c
各自獨立為烴基或經雜原子取代之烴基,且其中R1a-i
及R2a-c
中之任何兩者可連接形成飽和或不飽和、芳族或非芳族環;其限制條件為當與N連接時,R1a-i
不為H。
在第十二態樣中,本發明係關於一種包含第十一態樣之化合物之OLED裝置。
在第十三態樣中,本發明係關於一種對應於第十一態樣之配位體之化合物,其中金屬已由H置換。
在第十四態樣中,本發明係關於一種包含選自表1之金屬錯合物之化合物。
在第十五態樣中,本發明係關於一種包含第十四態樣之化合物之OLED裝置。
下表1提供使用G98/B31yp/cep-31g基底函數組進行密度泛函數理論(DFT)計算來估計本發明之各種化合物之HOMO、LUMO、能隙、偶極、S1及T1。
除非另有說明,否則本文所述之磷光金屬錯合物之製備及純化在暗室光中或使用黃色濾光片濾光或使用鋁箔包覆之玻璃器皿來進行以將金屬錯合物之光氧化降至最低。錯合物之敏感性相差較大。舉例而言,某些錯合物(諸如es20)僅需要適度小心而某些錯合物(諸如es1)在空氣中及在某些鹵化溶劑中極易光誘導分解。除非另有特定說明,否則分離面式異構體。
步驟1
將啡啶酮(5.0公克,0.027 mol)添加至含有五氯化磷(6.1公克,0.29 mol)及50 mL磷醯氯之反應燒瓶中。將反應混合物回流1小時,冷卻至室溫且以甲苯稀釋。在旋轉蒸發器上移除過量磷醯氯及甲苯。
將殘留物溶解於乙酸乙酯中且以蒸餾水繼而鹽水洗滌。將溶劑層經硫酸鎂乾燥,過濾且濃縮得到呈灰白色固體之pl2-il
(5.5公克,96%)。由質譜及1
H NMR確認產物且直接將產物用於下一步驟。
步驟2
將來自步驟1之化合物pl2-il
(5.5公克,0.026 mol)添加至含有溶解於200 mL二甘醇二甲醚中之胺基乙醛縮二甲醇(6.8公克,0.0646 mol)之反應燒瓶中,加熱至回流且在氮氣氛下攪拌。72小時之後如由TLC測定反應完成。將反應混合物冷卻至室溫且蒸餾移除過量溶劑。將殘留物溶解於二氯甲烷中且藉由真空過濾移除不溶物。經硫酸鎂乾燥溶劑,過濾且濃縮。藉由矽膠層析法使用80%乙酸乙酯及20%二氯甲烷作為溶離劑純化粗產物。收集經純化產物,以己烷洗滌且乾燥得到呈灰白色固體之pl2-H
(2.6公克,產率46%)。
步驟3
將來自以上步驟2之化合物pl2-H
(0.67 g,3.1 mmol)及乙醯丙酮銥(III)(0.38公克,0.77 mmol)在氮氣氛下加熱至250℃隔夜。反應物冷卻之後,將殘留物溶解於乙酸乙酯與二氯甲烷之1:1混合物中,過濾且藉由第一矽膠層析法使用1:1乙酸乙酯:己烷,繼而藉由第二矽膠管柱使用1:1氯仿:己烷純化得到呈米色固體之es1(0.15公克,產率23%)。二氯甲烷溶液中之磷光高能峰集中在458 nm,CIE座標0.18,0.27。
向1 L圓底燒瓶中添加2-碘-4,5-二甲基苯胺(24.7 g,100 mmol)、2-氰基苯基酸、四甲基乙二醇酯(27.5 g,120 mmol)、二氯雙(三苯膦)鈀(II)(3.51 g,5 mmol)、單水合磷酸三鉀(46.0 g,200 mmol)及400 mL甲苯。將反應物加熱至回流且在氮氣氛下攪拌4小時。冷卻之後,過濾所形成之沉澱物且以甲苯、己烷及水洗滌。產量為14 g。
向1 L圓底燒瓶中添加上述中間體、氯乙醛(水中之50重量%,15.7 g,100 mmol)、碳酸鈉(15.9 g,150 mmol)及300 mL 2-丙醇。將混合物加熱至回流歷時2小時。移除溶劑且以CH2
Cl2
萃取殘留物且進一步以矽膠管柱純化。產量為13 g。
以下程序在暗室光中或在光源上使用黃色濾光片或使用鋁箔包覆之玻璃器皿來進行以將金屬錯合物之光氧化降至最低。將6,7-二甲基咪唑并[1,2-f]啡啶(1.68 g,6.8 mmol)及參(乙醯丙酮)銥(III)(0.59 g,1.4 mmol)裝入50 mL史蘭克支管燒瓶(Schlenk tube flask)中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es12
(0.30 g)。由1
H NMR分析確認結構及純度。λmax
發射=456,486 nm(在CH2
Cl2
溶液中在室溫下);CIE=(0.18,0.23)。
將8b,13-二氮-茚并[1,2-f]非(3.49 g,13 mmol)及參(乙醯丙酮)銥(III)(1.27 g,2.6 mmol)裝入史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es3
(1.4 g)。1
H NMR結果確認所需化合物。發射λmaX
=492,524 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.23,0.51)。
將10-異丙基-8b,13-二氮-茚并[1,2-f]菲(6.07 g,19.6 mmol)及參(乙醯丙酮)銥(III)(1.91 g,3.92 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es4
(0.7 g)。1
H NMR結果確認所需化合物。發射λmaX
=496 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.26,0.57)。
步驟1:4-溴-6-胺基啡啶之合成
將2,6-二溴苯胺(143.51 g,0.57 mol)、2-氰基苯基酸丙二酯(34.35 g,0.19 mol)、K3
PO4
.H2
O(43.89 g,0.1906 mol)、PdCl2
(PPh3
)2
(6.67 g,9.5 mmole)及無水甲苯(700 ml)裝入3頸1 L圓底燒瓶中。在氮氣氛下將反應混合物加熱至100℃歷時6小時。接著將反應混合物濃縮至乾燥且使其經歷管柱層析法以獲得標題化合物(19.11 g,36.7%)。
步驟2:5-溴-咪唑并[1,2-f]啡啶之合成
向4-溴-6-胺基啡啶(19.11 g,69.91 mmole)、碳酸氫鈉(12.3 g,146 mmole)於2-丙醇(200 ml)中之混合物中添加氯乙醛(50%水溶液,17.35 g)。將反應混合物在75℃下加熱5小時之後,移除溶劑。將殘留物再溶解於二氯甲烷中且以水洗滌。將有機部分組合,經硫酸鈉乾燥,過濾且在真空下濃縮。藉由矽膠層法使用己烷/乙酸乙酯(80/20)純化粗混合物獲得標題化合物(13 g,62%)。
步驟3:5-(4-異丙苯基)-咪唑并[1,2-f]啡啶之合成
將5-溴-咪唑并[1,2-f]啡啶(4.55 g,15.31 mmole)、4-異丙苯基酸(3.59 g,21.89 mmole)、碳酸鉀(2 N水溶液,27 ml)、Pd(OAc)2
(223 mg,0.99 mmole)、三苯膦(1.044 g,3.98 mmole)及100 ml 1,2-二甲氧基乙烷裝入3頸1 L圓底燒瓶中。在氮氣氛下將反應混合物加熱至80℃歷時17小時。將反應混合物以二氯甲烷稀釋且以鹽水洗滌。將有機部分組合,經硫酸鈉乾燥,過濾且在真空下濃縮。藉由矽膠層析法使用己烷/乙酸乙酯(80/20)純化粗混合物獲得純5-(4-異丙苯基)-咪唑并[1,2-f]啡啶(4 g,77%)。
步驟4:錯合
將5-(4-異丙苯基)咪唑并[1,2-f]啡啶(2.94 g,8.74 mmol)及參(乙醯丙酮)銥(III)(0.86 g,1.75 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es7
(0.7 g)。1
H NMR結果確認所需化合物。發射λmaX
=496 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.26,0.57)。
步驟1:配位體合成
向500 mL圓底燒瓶中添加7-氯咪唑并[1,2-f]啡啶(3.8 g,15 mmol,自通用程序A製備)、4-異丙苯基酸(3.7 g,23 mmol)、乙酸鈀(II)(0.084 g,0.38 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,0.31 g,0.75 mmol)、單水合磷酸三鉀(6.9 g,30 mmol)及200 mL甲苯.將反應物加熱至回流且在氮氣氛下攪拌12小時。冷卻之後,以矽膠管柱純化混合物。產量為3.8 g。
步驟2:錯合
將7-(4-異丙苯基)咪唑并[1,2-f]啡啶(3.8 g,11.3 mmol)及參(乙醯丙酮)銥(III)(1.11 g,2.26 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es10
(1.2 g)。1
H NMR結果確認所需化合物。發射λmaX
=464,492 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.20,0.32)。
步驟1:配位體合成
向500 mL圓底燒瓶中添加7-氯咪唑并[1,2-f]啡啶(5.2 g,20.6 mmol,自通用程序A製備)、參(乙醯丙酮)鐵(III)(0.35 g,1.0 mmol)、30 mL NMP及300 mL無水THF。在室溫下伴隨攪拌向此混合物中逐滴添加15 mL環己基氯化鎂溶液(醚中之2 M)。添加之後反應完成。以I N HCl溶液中止混合物。以矽膠管柱進行一般處理及純化之後,產量為3.4 g。
步驟2:錯合
將7-環己基咪唑并[1,2-f]啡啶(3.4 g,11.2 mmol)及參(乙醯丙酮)銥(III)(1.1 g,2.25 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。
冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es8
(1.5 g)。1
H NMR結果確認所需化合物。發射λmaX
=462,486 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.17,0.27,)。
步驟1:配位體合成
向500 mL圓底燒瓶中添加7-氯咪唑并[1,2-f]啡啶(5.1 g,20 mmol,自通用程序A製備)、2,4,6-三異丙苯基酸(9.9 g,40 mmol)、Pd2
(dba)3
(0.92 g,1.0 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,1.64 g,4.0 mmol)、單水合磷酸三鉀(12.7 g,60 mmol)及200 mL甲苯。將反應物加熱至回流且在氮氣氛下攪拌72小時。冷卻之後,以矽膠管柱純化混合物。產量為2.6 g。
步驟2:錯合
將7-(2,4,6-三異丙苯基)咪唑并[1,2-f]啡啶(2.6 g,6.2 mmol)及參(乙醯丙酮)銥(III)(0.61 g,1.2 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es18
(0.3 g)。1
H NMR結果確認所需化合物。發射λmaX
=464,488 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.17,0.29)。
步驟1
向1 L圓底燒瓶中添加7-甲基咪唑并[1,2-f]啡啶(5.7 g,24.5 mmol,自通用程序A製備)及200 mL無水DMF。在室溫下在黑暗中伴隨攪拌向此混合物中逐滴添加100 mL N-溴代琥珀醯亞胺DMF溶液(4.6 g,25.7 mmol)。將反應混合物繼續攪拌隔夜。接著伴隨攪拌將混合物傾入1 L水中。過濾收集沉澱物,且進一步將其以大量水洗滌,且最終以MeOH(50 mL×2)洗滌,且接著乾燥。3-溴-7-甲基咪唑并[1,2-f]啡啶之產量為6.5g。
步驟2
向500 mL圓底燒瓶中添加3-溴-7-甲基咪唑并[1,2-f]啡啶(6.2 g,20 mmol)、2,6-二甲苯基酸(9.0 g,60 mmol)、Pd2
(dba)3
(4.58 g,5.0 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,8.2 g,20 mmol)、磷酸三鉀(17.0 g,80 mmol)及200 mL甲苯。將反應物加熱至回流且在氮氣氛下攪拌84小時。冷卻之後,以矽膠管柱純化混合物。產量為4.0 g。
步驟3
將3-(2,6-二甲苯基)-7甲基咪唑并[1,2-f]啡啶(3.3 g,10 mmol)及參(乙醯丙酮)銥(III)(0.98 g,2.0 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es20
(0.8 g)。1
H NMR結果確認所需化合物。發射λmaX
=466,492 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.17,0.30)。
步驟1
向1 L圓底燒瓶中添加6,7-二甲基咪唑并[1,2-f]啡啶(13.0 g,52.8 mmol,自通用程序A製備)及400 mL無水DMF。在室溫下在黑暗中伴隨攪拌向此混合物中逐滴添加150 mL N-溴代琥珀醯亞胺DMF溶液(10.3 g,58 mmol)。將反應混合物繼續攪拌隔夜。接著伴隨攪拌將混合物傾入1 L水中。過濾收集沉澱物,且進一步將其以大量水洗滌,且最終以MeOH(50 mL×2)洗滌,且乾燥。3-溴-6,7-二甲基咪唑并[1,2-f]啡啶之產量為14.7g。
步驟2
向500 mL圓底燒瓶中添加3-溴-6,7二甲基咪唑并[1,2-f]啡啶(6.5 g,20 mmol)、2,6-二甲苯基酸(9.0 g,60 mmol)、Pd2
(dba)3
(4.58 g,5.0 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,8.2 g,20 mmol)、磷酸三鉀(17.0 g,80 mmol)及200 mL甲苯。將反應物加熱至回流且在氮氣氛下攪拌84小時。冷卻之後,以矽膠管柱純化混合物。產量為2.6 g。
步驟3
將3-(2,6-二甲苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(2.6 g,7.4 mmol)及參(乙醯丙酮)銥(III)(0.73 g,1.5 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es21
(0.35 g)。1
H NMR結果確認所需化合物。發射λmaX
=460,490 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.16,0.27)。
步驟1
向500 mL圓底燒瓶中添加5-溴-7-第三丁基咪唑并[1,2-f]啡啶(3.9 g,11 mmol,自通用程序A製備)、2,6-二甲苯基酸(3.5 g,23 mmol)、Pd2
(dba)3
(0.51 g,0.56 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,0.91 g,2.2 mmol)、磷酸三鉀(7.2 g,34 mmol)及60 mL甲苯。將反應物加熱至回流且在氮氣氛下攪拌48小時。冷卻之後,以矽膠管柱純化混合物。產量為1.2 g。
步驟2
將5-(2,6-二甲苯基)-7-第三丁基咪唑并[1,2-f]啡啶(0.40 g,1.1 mmol)及參(乙醯丙酮)銥(III)(0.10 g,0.2 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱24小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到面式參銥(III)(0.01 g)。1
H NMR結果確認所需化合物。發射λmaX
=462,488 nm(CH2
Cl2
溶液,在室溫下)。
步驟1
向500 mL圓底燒瓶中添加3-溴-6,7二甲基咪唑并[1,2-f]啡啶(8.2 g,25.2 mmol)、2,6-二氯苯基酸(19.2 g,100.9 mmol)、Pd2
(dba)3
(2.29 g,2.5 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,4.11 g,10.0 mmol)、磷酸三鉀(26.7 g,126 mmol)及250 mL甲苯。將反應物加熱至回流且在氮氣氛下攪拌48小時。冷卻之後,以矽膠管柱純化混合物。3-(2,6-二氯苯基)-6,7-二甲基咪唑并[1,2-f]啡啶之產量為2.4 g。
步驟2
向500 mL圓底燒瓶中添加3-(2,6-二氯苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(2.4 g,6.1 mmol)、苯基酸(3.74 g,30 mmol)、Pd2
(dba)3
(1.1 g,1.2 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,1.97 g,4.8 mmol)、磷酸三鉀(7.64 g,36 mmol)及100 mL甲苯。將反應物加熱至回流且在氮氣氛下攪拌12小時。冷卻之後,以矽膠管柱純化混合物。3-(2,6-二苯基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶之產量為0.9 g。
步驟3
將3-(2,6-二苯基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(0.095 g,0.2 mmol)及參(乙醯丙酮)銥(III)(0.025 g,0.05 mmol)裝入25 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱24小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es22
(0.01 g)。1
H NMR結果確認所需化合物。發射λmaX
=468,496 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.19,0.35)。
將7-正十二烷基咪唑并[1,2-f]啡啶(3.66 g,9.34 mmol,經由通用程序A製備)及參(乙醯丙酮)銥(III)(0.92 g,1.87 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es25
(1.5 g)。1
H NMR結果確認所需化合物。
步驟1:2-(1,3,2-二氧硼 -2-基)苯甲腈之合成
在2 L圓底燒瓶中伴隨攪拌將49.0 g(334 mmol)2-氰基苯酸及25.9 g(340 mmol)1,3-丙二醇溶解於1 L CH2
Cl2
中歷時20 h。接著伴隨抽吸將溶液傾至過濾器上以移除膠狀固體。接著以無水MgSO4
乾燥濾液以移除殘留水份,過濾且蒸發溶劑得到輕度有色之油狀物。接著將油狀物溶解於CH2
Cl2
中且在矽膠栓上使用CH2
Cl2
作為溶離劑純化。
蒸發產物溶離份得到呈澄清油狀物之產物(35.7 g,產率57.2%)。
步驟2:2-(第三丁基)-6-胺基啡啶之合成
在含有400 ml甲苯及300 mL乙醇之2 L燒瓶中將35.7 g(190 mmol)2-(1,3,2-二氧硼-2-基)苯甲腈、31.9 g(158 mmol)2-溴-4-(第三丁基)苯胺、3.6 g(3.16 mmol)肆(三苯膦)鈀(0)及59.0 g(427 mmol)K2
CO3
加熱至回流。在恆定N2
淨化下將反應混合物加熱19小時。反應混合物之HPLC指示起始苯胺之消耗。冷卻混合物且接著過濾移除鹼。以EtOAc洗滌鹼以移除痕量有機物。蒸發經組合之濾液得到不純油狀物。在二氧化矽管柱上使用95/5/.05 CH2
Cl2
/MeOH/NH4
OH作為溶離劑純化油狀物獲得分離。蒸發產物溶離份之溶劑且使所得殘留物自CH2
Cl2
/己烷再結晶得到14.0 g呈白色固體之目標化合物(產率35.5%,由GC-MS確認)。
步驟3:es9配位體之合成
將13.0 g(52 mmol)2-(第三丁基)-6-胺基啡啶、12.3 g(78 mmol,H2
O中50% v/v)氯乙醛及8.74 g(104 mmol)碳酸氫鈉添加至500 mL燒瓶中且在N2
氣氛下在200 mL 2-丙醇中回流35小時。完成後,冷卻混合物,同時TLC及HPLC指示起始啡啶完全消耗。將混合物溶解於乙酸乙酯中且過濾移除鹼。接著蒸發濾液得到淺琥珀色油狀物。在二氧化矽管柱上使用95/5/.05 CH2
Cl2
/MeOH/NH4
OH作為溶離劑純化油狀物。或者,可使用Al2
O3
管柱自動層析法且使用2% EtOAc/己烷-20% EtOAc/己烷梯度作為溶離劑純化配位體。蒸發此等純化之產物溶離份之溶劑且自二氯甲烷/己烷再結晶得到共10.8 g呈白色固體之es9
配位體(產率76.1%,經NMR確認)。
步驟4
將10.6 g(38.7 mmol)es9
配位體及4.76 g(9.7 mmol)Ir(acac)3
添加至具備攪拌棒之50 mL史蘭克試管中。添加20滴十三烷,以隔膜將試管密封且以N2
徹底進行真空脫氣。將試管浸於沙浴中且在N2
氣氛下在245℃下加熱72小時。接著將冷卻混合物溶解於CH2
Cl2
中,使用超音波處理溶解雜質。在真空中過濾混合物,且以CH2
Cl2
及己烷沖洗固體得到8.5 g之量之深黃色固體。接著將固體溶解於1 L沸騰氯苯中且傾至矽藻土墊(熱)上以移除雜質。將所得濾液蒸發至500 mL,使摻雜劑以亮黃色固體形式再結晶(6.5 g,產率66.4%,經NMR確認,HPLC檢定99.3%)。作為另外之純化方法,將3.5 g摻雜劑在3區昇華器中在370℃及1.0×10-5
托真空下昇華得到400 mg呈亮黃色固體之es9
(HPLC檢定100%)。
步驟1:2-(正己基)-6-胺基啡啶之合成
將13.1 g(69.8 mmol)2-(1,3,2-二氧硼-2-基)苯甲腈、16.3 g(63.4 mmol)2-溴-4-己基苯胺、1.62 g(1.40 mmol)肆(三苯膦)鈀(0)及23.6 g(171 mmol)碳酸鉀在250 ml甲苯及100 ml EtOH中在N2
氣氛下回流20小時。HPLC及TLC顯示苯胺幾乎完全消耗。冷卻反應混合物且使其穿過過濾器。以乙酸乙酯洗滌固體以自所收集之鹼移除有機物。接著蒸發濾液且在二氧化矽上乾燥。使用矽膠層析法以100%乙酸乙酯作為溶離劑純化樣本。接著將產物溶離份蒸發至最小量且添加己烷以使產物以灰白色固體形式結晶(7.05 g,產率39.8%,經GC-MS確認)。
步驟2:es8配位體之合成
將7.02 g(25.2 mmol)2-(正己基)-6-胺基啡啶、2.99 g(37.8 mmol,H2
O中50% v/v)氯乙醛及4.24 g(50.4 mmol)碳酸氫鈉添加至500 mL燒瓶中且在N2
氣氛下在150 mL 2-丙醇中回流20小時。完成後,冷卻混合物,同時TLC及HPLC指示起始啡啶完全消耗。將混合物溶解於EtOAc中且過濾移除鹼。接著蒸發濾液得到淺琥珀色油狀物。接著在二氧化矽上乾燥油狀物且在二氧化矽管柱上使用70%乙酸乙酯/己烷-100%乙酸乙酯作為溶離劑純化。蒸發此純化之產物溶離份之溶劑且自乙酸乙酯/己烷再結晶得到共4.9 g呈白色固體之es8
配位體(產率55.1%,經GC-MS確認)。
步驟3
將2.9公克(9.6 mmol)es8
配位體、0.94 g(1.9 mmol)乙醯丙酮銥及20滴十三烷裝入50 ml史蘭克試管中。抽空反應器且重新填充氮氣3次。將反應物加熱至240℃歷時70小時。冷卻反應物且添加二氯甲烷。藉由管柱層析法使用二氯甲烷作為溶離劑純化產物。組合含有所需產物之溶離份且藉由旋轉蒸發移除溶劑。使產物自甲苯結晶得到300 mges8
,藉由昇華進一步將其純化。
步驟1:2-溴啡啶酮之合成
將99.8 g(511 mmol)啡啶酮添加至具備攪拌臂及冷凝器
之3 L多頸燒瓶中。添加1.2 L冰乙酸且將混合物在150 rpm下攪拌且加熱至回流。經3小時之時期將懸浮於100 ml乙酸中之90 g(562 mmol)Br2
逐滴添加至回流溶液中。添加之後,檢定混合物且顯示約80%完成。基於此檢定,將額外20 g Br2
(在30 mL乙酸中)逐滴添加至回流混合物中。此添加之後,檢定大於90%完成。逐滴添加最終20 g Br2
(在30 mL乙酸中)且在添加之後將混合物攪拌1小時。最終檢定為大於97%。冷卻混合物且添加1 L水且過濾混合物。接著在硫代硫酸鈉水溶液中攪拌濕潤固體以破壞殘留之溴且再過濾。以H2
O沖洗此等固體且在真空中乾燥以移除殘留水份。接著使固體自硝基苯(大於2公升)再結晶,且以漏斗收集得到128 g 2-溴啡啶酮(產率90.8%)。
步驟2:2-溴-6-氯啡啶之合成
將36.7 g(139 mmol)2-溴啡啶酮及30.7 g(147 mmol)PCl5
以及350 mL POCl3
添加至1 L多頸燒瓶(具備攪拌臂、冷凝器及鹼收集器)中且在93℃下加熱16小時(注意:HCl氣體之析出經鹼收集器顯著破壞)。隨後,檢定混合物確定2-溴啡啶酮完全消耗。將迪恩斯達克(dean stark)收集器與燒瓶連接以移除1/2體積溶劑。隨後,添加等體積甲苯且蒸餾移除大部分POCl3
。第三次添加甲苯之後,體積減至300 mL且經由旋轉蒸發移除剩餘溶劑。接著使固體自甲苯再結晶且乾燥得到30.8 g(產率78.6%,檢定98%)呈灰白色固體之2-溴-6-氯啡啶(經GC-MS確認)。
步驟3:es13-i1之合成
將20 g 4 A乾燥分子篩添加至具備攪拌臂及冷凝器之2 L多頸燒瓶中。將73.8 g(252 mmol)2-溴-6-氯啡啶及79.4 g(756 mmol)胺基乙醛縮二甲醇以及750 mL無水二甘醇二甲醚添加至燒瓶中。使用機械攪拌將混合物在135℃下在N2
氣氛下加熱18小時。混合物之HPLC顯示起始材料完全消耗。接著冷卻反應物且添加乙酸乙酯。自燒瓶側壁刮除成塊固體。接著在真空中過濾混合物且棄去濾液。接著使用研缽及杵將來自漏斗之固體碾碎(乾燥時)且添加至1 L燒瓶中且在600 mL氯苯中回流。過濾氯苯混合物且組合濾液。接著經由旋轉蒸發移除溶劑得到深色固體。接著在大型二氧化矽管柱上使用CH2
Cl2
及CH2
Cl2
/MeOH作為溶離劑純化固體(注意:當將產物之CH2
Cl2
溶液置於管柱頂時,並非所有之固體均溶解。經由添加額外溶離劑,固體才最終溶解)。在延長層析法之後,將產物溶離份之溶劑蒸發且以CH2
Cl2
/己烷清洗固體。過濾固體得到乾燥時62.0公克之標題化合物(產率83.1%,經NMR確認)。
步驟4:es13配位體之合成
將3.12 g(10.5 mmol)7[溴]-咪唑并[1,2-f]啡啶、3.93 g(26.2 mmol)2,6-二甲苯基酸、0.18 g(0.53 mmol)2-(二環己基膦基)聯苯、0.13 g(0.14 mmol)Pd2
(dba)3
及6.68 g(31.5 mmol)磷酸鉀添加至具備攪拌棒之50 mL無空氣燒瓶中且以N2
真空脫氣。添加20 mL無水間二甲苯且將混合物置於130℃ N2
氣氛下。16小時之後混合物之HPLC顯示起始啡啶完全消耗。向混合物添加乙酸乙酯及二氯甲烷且過濾移除鹼。接著將濾液與854-8741-076(1 g等級rxn)混合且蒸發得到深色油狀物。在二氧化矽上(使用二氯甲烷)乾燥油狀物且使用自動層析法使用5% EtOAc/己烷-50% EtOAc/己烷梯度經1小時之時期層析產物。蒸發純溶離份得到3.40 g卡其色固體(產率76.2%,HPLC檢定98%,經NMR確認)。
步驟5
將3.40 g(10.6 mmol)7-(2,6-二甲苯基)-咪唑并[1,2-f]啡啶及1.30 g(2.6 mmol)乙醯丙酮銥(IIl)以及12滴十三烷添加至具備攪拌棒之25 mL史蘭克試管中。將燒瓶密封且以N2
真空脫氣。接著將混合物浸於沙浴中且在N2
氣氛下在250℃下加熱96小時。接著將混合物溶解於二氯甲烷中且在二氧化矽管柱上使用二氯甲烷作為溶離劑純化。將產物溶離份之溶劑蒸發得到粗摻雜劑。接著使固體自二氯甲烷/甲醇再結晶得到2.1 g呈黃色固體之es13
(產率68.9%,HPLC檢定99.5%,經NMR確認)。
步驟1:2-(正丁基)-6-胺基啡啶之製備
將20.0 g(87.7 mmol)2-(1,3,2-二氧硼-2-基)苯甲腈、13.7 g(73.1 mmol)2-溴-4-丁基苯胺、1.70 g(1.46 mmol)肆(三苯膦)鈀(0)及27.2 g(198 mmol)碳酸鉀在400 ml甲苯及200 ml乙醇中在N2
氣氛下回流20 h。HPLC及TLC顯示苯胺幾乎完全消耗。添加額外1.8 g 2-(1,3,2-二氧硼-2-基)苯甲腈且繼續回流額外18 h。冷卻反應混合物且使其穿過過濾器。以乙酸乙酯洗滌固體以自所收集之鹼移除有機物。接著蒸發濾液且在二氧化矽上乾燥。使用矽膠層析法以100%乙酸乙酯作為溶離劑純化樣本。接著將產物溶離份蒸發至最小量且使產物自EtOAc/己烷再結晶得到12.0 g呈淺黃色固體之標題化合物(產率65.9%,經GC-MS確認)。
步驟2:es15配位體之合成
將12.0 g(48.0 mmol)2-(正丁基)-6-胺基啡啶、11.4 g(72.0 mmol,H2
O中50% v/v)氯乙醛及8.06 g(96.0 mmol)碳酸氫鈉添加至500 mL燒瓶中且在N2
氣氛下在200 mL 2-丙醇中回流20小時。完成後,冷卻混合物,同時TLC及HPLC指示起始啡啶完全消耗。將混合物溶解於EtOAc中且過濾移除鹼。接著蒸發濾液得到棕色油狀物。接著在二氧化矽上乾燥油狀物且在二氧化矽管柱上使用70%乙酸乙酯/己烷-100%乙酸乙酯作為溶離劑純化。蒸發此純化之產物溶離份之溶劑且自乙酸乙酯/己烷再結晶得到共5.22 g呈灰白色固體之es15
配位體(產率40.5%,經NMR確認)。
步驟3
將5.2 g(21.0 mmol)es15
配位體及2.58 g(5.25 mmol)乙醯丙酮銥(III)添加至具備攪拌棒之25 mL史蘭克試管中。添加10滴十三烷,以隔膜將試管密封且以N2
徹底進行真空脫氣。將試管浸於沙浴中且在N2
氣氛下在250℃下加熱72 h。接著將冷卻混合物溶解於CH2
Cl2
中,使用超音波處理溶解雜質。在真空中過濾混合物,且以CH2
Cl2
及己烷沖洗固體得到2.74 g之量之黃色固體。接著將固體溶解於130 mL沸騰氯苯中且傾至矽藻土墊(熱)上以移除雜質。將所得濾液蒸發至乾燥。將殘留物溶解於二氯甲烷中且在矽膠管柱上使用二氯甲烷快速純化內含物。蒸發產物溶離份之溶劑且使固體自氯苯再結晶得到1.52 g呈黃色固體之es15
(產率29.6%,經NMR確認,HPLC檢定96.3%),藉由在3區昇華器中在360℃及1.0×10-5
托真空下昇華進一步純化1.5 g該固體得到160 mg呈亮黃色固體之es15
。
步驟1:2-異丙基-啡啶-6-基胺之合成
將12.2公克(65.4 mmol)2-氰基苯基酸丙二醇酯、14.0 g(65.4 mmol)2-溴-4-異丙基苯胺、2.27(2 mmol)肆(三苯膦)鈀、18.0 g(131 mmol)碳酸鉀、150 ml甲苯及50 ml乙醇裝入500 ml圓底燒瓶中。在N2
下將反應物加熱至回流歷時18小時。冷卻至室溫之後,以乙酸乙酯及水萃取反應物。將有機物以鹽水洗滌且接著以硫酸鎂乾燥。過濾收集固體且自濾液移除溶劑。藉由矽膠層析法使用94.5%二氯甲烷、5%甲醇、0.5%氫氧化銨作為溶離劑純化產物。組合含有所需產物之溶離份且移除溶劑。由NMR及質譜確認產物。
步驟2:es6配位體之合成
將5公克(21.2 mmol)2-異丙基-啡啶-6-基胺、5公克(31.8 mmol,水中之50%溶液)氯乙醛、3.56公克(42.4 mmol)碳酸氫鈉及150 ml異丙醇裝入250 ml圓底燒瓶中。將混合物加熱至回流歷時18小時且接著冷卻至室溫。添加二氯甲烷且過濾固體。藉由旋轉蒸發移除溶劑且藉由管柱層析法使用40%己烷/乙酸乙酯作為溶離劑純化產物。組合含有所需產物之溶離份且移除溶劑。藉由庫格若蒸餾(Kugelrohr distillation)進一步純化產物。收集5.8公克es6
配位體。
步驟3
將2.8公克(10.8 mmol)7-異丙基-咪唑并[1,2-f]啡啶及1.05 g(2.2 mmol)乙醯丙酮銥裝入50 mL史蘭克試管中。抽空反應器且重新填充氮氣3次。將反應物加熱至250℃歷時24小時。冷卻反應物且添加二氯甲烷,且接著過濾固體得到1.5公克黃色固體。將固體溶解於熱1,2-二氯苯中。冷卻混合物且過濾固體得到0.4公克呈黃色固體之es6
。藉由昇華進一步純化材料。
將2.9公克(9.6 mmol)es8
配位體、0.94 g(1.9 mmol)乙醯丙酮銥及20滴十三烷裝入50 ml史蘭克試管中。抽空反應器且重新填充氮氣3次。將反應物加熱至240℃歷時70小時。冷卻反應物且添加二氯甲烷。藉由管柱層析法使用二氯甲烷作為溶離劑純化產物。組合含有所需產物之溶離份且藉由旋轉蒸發移除溶劑。使產物自甲苯結晶得到300 mges8
,藉由昇華進一步將其純化。
步驟1:9-氟-6-啡啶胺之合成
向2-氯-4-氟苯甲腈(1.0 g,6.42 mmol)、2-胺基苯基酸四甲基乙二醇酯(1.6 g,7.1 mmol)、乙酸鈀(II)(0.07 g,0.32 mmol)、鹽酸三環癸胺(0.24 g,1.3 mmol)及碳酸銫(4.6 g,14.1 mmol)之溶液中添加預先以氮除氣之二噁烷且加熱至回流歷時17小時。冷卻之後,將蒸餾水與二氯甲烷(50 mL)添加至反應混合物中。分離溶劑層且濃縮得到粗油狀物,將其藉由管柱層析法首先使用1:1乙酸乙酯與己烷比率繼而4:1乙酸乙酯/己烷作為溶離劑純化。收集純產物得到9-氟-6-啡啶胺(42 g,產率32%),其NMR譜與設想結構一致。
步驟2:10-氟-咪唑并[1,2-f]啡啶之合成
將9-氟-6-啡啶胺(0.8 g,3.7 mmol)及含有碳酸氫鈉(0.6 g,7.54 mmol)之乙醯氯(0.4 g,5.66 mmol)於水中之50%溶液溶解於異丙醇(25 mL)中。將反應混合物在氮氣墊下回流17小時。將反應混合物冷卻至室溫且真空過濾沉澱物且將其以二氯甲烷洗滌。藉由管柱層析法使用1:1比率之乙酸乙酯與己烷作為溶離劑純化粗產物,繼而蒸餾得到10-氟-咪唑并[1,2-f|啡啶(0.46 g,產率52%)。
步驟3
將2.1公克(9.6 mmol)10-氟-咪唑并[1,2-f]啡啶、0.87 g(1.9 mmol)乙醯丙酮銥及15滴十三烷裝入50 mL史蘭克試管中。抽空反應器且重新填充氮氣3次。將反應物加熱至230℃歷時40小時。冷卻反應物且添加二氯甲烷。藉由管柱層析法使用二氯甲烷作為溶離劑純化產物。組合含有所需產物之溶離份且藉由旋轉蒸發移除溶劑。使產物自二氯甲烷/己烷混合物結晶得到500 mges5
,藉由昇華進一步將其純化。
步驟1:3-第三丁基苯基 酸之合成
向無水THF(10 mL)之溶液中添加鎂(1.25 g,52 mmol)、3-第三丁基溴苯(2.0 g,9.4 mmol)及碘晶體。首先將反應物微微加熱直至反應開始且接著移除加熱。經由加料漏斗添加剩餘之3-第三丁基溴苯(8.0 g,37.7 mmol)直至自發回流停止。將反應混合物加熱至回流歷時2小時。將格林納試劑(Grignard)經由注射器轉移至溶解於THF中之硼酸三甲酯之冷卻溶液(-40℃)中且經10分鐘之時期添加。使反應混合物升溫至室溫隔夜。將乙酸乙酯及蒸餾水添加至反應混合物中且將層分離。將有機物以鹽水洗滌且經硫酸鎂乾燥。濃縮溶劑且藉由矽膠管柱使用10%乙酸乙酯及己烷作為溶離劑純化產物得到呈白色固體之3-第三丁基苯基酸(4.0 g,產率46%)。由GCMS確認產物且將其直接用於下一步驟。
步驟2:2-胺基-3',5-二-第三丁基聯苯之合成
將3-第三丁基苯基酸(4.0 g,22.4 mmol)、2-溴-4-第三丁基苯胺(4.3 g,18.7 mmol)、乙酸鈀(II)(0.11 g,0.468 mmol)、三苯膦(0.5 g,1.8 mmol)及25 mL碳酸鉀於36 mL乙二醇二甲醚中之2 M溶液添加在一起。將反應混合物回流加熱18小時。將反應物冷卻至室溫且將水相與有機相分離。以乙酸乙酯萃取水相。組合有機萃取物,將其經硫酸鎂乾燥,過濾且濃縮。藉由管柱層析法使用20%乙酸乙酯及己烷作為溶離劑純化粗產物。收集呈白色固體之純產物2-胺基-3',5-二-第三丁基聯苯(3.0 g,產率57%),其NMR與設想結構一致。
步驟3:N-甲醯基-2-胺基-3',5-二-第三丁基聯苯之合成
將2-胺基-3',5-二-第三丁基聯苯(2.0 g,7.11 mmol)添加至甲酸溶液中且加熱至回流歷時16小時。冷卻之後,將水(25 mL)添加至產物中且藉由真空過濾收集沉澱物。將粗產物溶解於乙酸乙酯中,以水洗滌。將有機物經硫酸鎂乾燥且濃縮且藉由管柱層析法使用10%乙酸乙酯及己烷作為溶離劑純化得到純N-甲醯基-2-胺基-3',5-二-第三丁基聯苯(1.8 g,產率82%)(如由GCMS所測定)。
步驟4:2,9-二-第三丁基啡啶酮之合成
將上述化合物N-甲醯基-2-胺基-3',5-二-第三丁基聯苯(6.5 g,21 mmol)溶解於50 mL氯苯中,向該溶液中添加5當量之過氧化二-第三丁基。將反應混合物加熱至110℃歷時72小時。將反應混合物濃縮至一半且冷卻至0℃。藉由真空過濾收集所形成之沉澱物。以己烷洗滌灰白色固體得到2,9-二-第三丁基啡啶酮(如由GCMS所測定)且不進行任何進一步純化。
步驟5:2,9-二-第三丁基-6-氯啡啶之合成
將上述2,9-二-第三丁基啡啶酮(3.0 g,9.7 mmole)添加至含有五氯化磷(3.0 g,14.6 mmole)及50 mL磷醯氯之反應燒瓶中。將反應混合物回流隔夜,冷卻至室溫且以甲苯稀釋。藉由旋轉蒸發器移除過量磷醯氯及甲苯。將殘留物溶解於乙酸乙酯中且以蒸餾水繼而鹽水洗滌。將溶劑層經硫酸鎂乾燥,過濾且濃縮得到呈灰白色固體之所需2,9-二-第三丁基-6-氯啡啶(3.0公克,98%)。由GC質譜確認產物且將其不經進一步純化而直接用於下一步驟。
步驟5:7,10-二-第三丁基-咪唑并[1,2-f]啡啶之合成
將2,9-二-第三丁基-6-氯啡啶(3.7公克,11.0 mmole)添加至含有溶解於200 mL二甘醇二甲醚中之胺基乙醛縮二甲醇(2.4公克,23 mmole)之反應燒瓶中,加熱至回流且在氮氣氛下攪拌。96小時之後如由TLC測定反應完成。將反應混合物冷卻至室溫且蒸餾移除過量溶劑。將殘留物溶解於二氯甲烷中。經硫酸鎂乾燥溶劑,過濾且濃縮。藉由矽膠層析法使用10%乙酸乙酯及90%二氯甲烷作為溶離劑純化粗產物。收集經純化產物,以己烷洗滌且乾燥得到呈白色固體之7,10-二-第三丁基-咪唑并[1,2-f]啡啶(2.0公克,產率56%)。
步驟6
將2.0公克(6.1 mmol)10-氟-咪唑并[1,2-f]啡啶、0.84 g(1.7 mmol)乙醯丙酮銥及10滴十三烷裝入50 mL史蘭克試管中。抽空反應器且重新填充氮氣3次。將反應物加熱至240℃歷時18小時。冷卻反應物且添加二氯甲烷。藉由管柱層析法使用二氯甲烷作為溶離劑純化產物。組合含有所需產物之溶離份且藉由旋轉蒸發移除溶劑。使產物自二氯甲烷/己烷混合物結晶得到0.6 mges19
,藉由昇華進一步將其純化。
步驟1:3,5-二甲基-6-啡啶胺之合成
將2-氰基苯基酸四甲基乙二醇酯(13.7 g,60 mmol)、2-溴-4,6-二甲基苯胺(10.0 g,50 mmol)、肆(三苯膦)鈀(0)(2.3 g,2.0 mmol)及碳酸鉀(18.6 g,138.21 mol)一起添加至125 mL甲苯/甲醇之95/5混合物中。將溶劑脫氣且將反應混合物加熱至回流歷時48小時。冷卻之後,真空過濾反應混合物且蒸發有機物,且使用矽膠管柱層析法以三乙胺及1:9乙酸乙酯與二氯甲烷混合物作為溶離劑處理來純化粗產物。收集純產物且濃縮得到3,5-二甲基-6-啡啶胺(9.1 g,產率82%)。
步驟2:5,7-二甲基-咪唑并[1,2-f]啡啶之合成
將258 mL異丙醇中之3,5-二甲基-6-啡啶胺(8.6 g,39 mmol)、乙醯氯(4.6 g,58 mmol)於水中之50%溶液、碳酸氫鈉(6.5 g,77.4 mmol)加熱至回流歷時40小時。冷卻之後,將粗產物溶解於二氯甲烷中且真空過濾。濃縮濾液且使粗產物在二氯甲烷與乙酸乙酯混合物中結晶。藉由真空過濾收集純產物得到5,7-二甲基-咪唑并[1,2-f]啡啶(3.8 g,產率40%)(如由NMR所測定)。
步驟3
將3.7 g(15.0 mmol)5,7-二甲基(咪唑并[1,2-f]啡啶)及1.85 g(3.76 mmol)Ir(acac)3
添加至具備攪拌棒之50 mL史蘭克試管中。添加12滴十三烷,且將試管密封且以N2
真空脫氣。接著將試管浸於沙浴中且加熱至250℃歷時72小時。冷卻反應混合物且以CH2
Cl2
超音波處理內含物以使其溶解。過濾黃色固體且在氯苯中加熱。經由矽藻土過濾溶液且濃縮以誘發結晶。過濾固體得到600 mg呈黃色固體之es14
,藉由昇華進一步將其純化。
步驟1:2-胺基-2'-甲基-聯苯之合成
將2-甲基苯基酸(24.7 g,181 mmol)、2-溴苯胺(25.7 g,151 mmol)、乙酸鈀(II)(0.85 g,3.78 mmol)、三苯膦(4.0 g,15.1 mmol)、碳酸鉀之2 M溶液(204 mL)及乙二醇二甲醚(223 mL)添加在一起且將反應混合物回流加熱18小時。將反應物冷卻至室溫之後,將水相與有機相分離。以乙酸乙酯萃取水相且將有機萃取物組合,經硫酸鎂乾燥且過濾。藉由矽膠管柱層析法使用己烷中之10%乙酸乙酯作為溶離劑純化粗產物。收集純溶離份,將其組合且濃縮得到2-胺基-2'-甲基-聯苯(23.5 g,產率84.8%),由GCMS及NMR確認其結構。
步驟2:N-乙氧羰基-2-胺基-2'甲基聯苯之合成
將上述化合物2-胺基-2'-甲基-聯苯(11.0 g,60 mmol)添加至含有三乙胺(24 g,24 mmol)之無水甲苯(250 mL)中且在氮氣墊下攪拌。將氯甲酸乙酯(26 g,240 mmol)經由注射器緩慢添加至經攪拌溶液中。以鹽水洗滌反應混合物且將有機物分離,經硫酸鎂乾燥且濃縮得到呈無色油狀物之N-乙氧羰基-2-胺基-2'甲基聯苯(7.0 g,產率46%),由GCMS及NMR確認其結構。
步驟3:10-甲基-啡啶酮之合成
將上述化合物N-乙氧羰基-2-胺基-2'甲基聯苯(6.7 g,26 mmol)添加至多磷酸(15 g)中且加熱至170℃隔夜。冷卻之後,添加水且藉由真空過濾收集白色沉澱物得到10-甲基-啡啶酮(3.5 g,產率65%),其結構與CGMS及NMR一致。
步驟4:6-氯-10-甲基啡啶之合成
將上述化合物10-甲基-啡啶酮(4.0公克,19 mmole)添加至含有五氯化磷(6.0公克,0.29 mol)及磷醯氯(50 mL)之反應燒瓶中。將反應混合物回流4小時,冷卻至室溫且以甲苯稀釋。藉由旋轉蒸發器移除過量磷醯氯及甲苯。將殘留物溶解於乙酸乙酯中且以蒸餾水繼而鹽水洗滌。將溶劑層經硫酸鎂乾燥,過濾且濃縮得到呈灰白色固體之6-氯-10-甲基啡啶(4.1公克,95%)。由質譜及NMR確認產物且將其不經進一步純化而直接用於下一步驟。
步驟5:es27i-1之合成
向二甘醇二甲醚(100 mL)之溶液中添加上述6-氯-10-甲基-啡啶(1.8 g,7.9 mmol)及2-溴-4-異丙基苯胺(3.4 g,15.8 mmol)。將反應混合物在氮氣墊下在160℃下攪拌3小時。冷卻之後,真空過濾沉澱物,以乙酸乙酯繼而已烷洗滌得到呈米色固體之es27i-1
(2.5 g,產率78%)。
步驟6:10-異丙基-3-甲基-8b,13-二氮-茚并[1,2-f]菲之合成
將上述化合物(3.5 g,8.7 mmol)溶解於含有三苯膦(0.45 g,1.7 mmol)、乙酸鈀(0.12 g,0.5 mmol)、碳酸鉀(3.6 g,26 mmol)之甲苯中。將反應混合物在氮氣墊下回流隔夜。將反應混合物冷卻至室溫且以蒸餾水繼而鹽水洗滌。分離有機層之後,在矽膠管柱上純化es27
配位體產物。
步驟7
將1.8 g(5.5 mmol)10-異丙基-3-甲基-8b,13-二氮-茚并[1,2-f]菲、0.67 g(1.4 mmol)乙醯丙酮銥及20 ml乙二醇裝入50 ml圓底燒瓶中。在氮氣氛下將反應物加熱至回流歷時24小時。冷卻反應物且添加甲醇,繼而過濾黃色固體。將固體溶解於二氯甲烷中且藉由管柱層析法以二氯甲烷作為溶離劑純化。組合含有所需產物之溶離份且藉由旋轉蒸發移除溶劑。使產物自氯苯結晶得到0.3 ges27
。
步驟1:es17i-1之合成
將2,6-二溴-4-第三丁基苯胺(38 g,0.124 mol)、2-氰基苯基四甲基乙二醇酯(10 g,0.044 mol)、K3
PO4
.H2
O(35.4 g,0.154 mol)、PdCl2
(PPh3
)2
(1.8 g,2.6 mmole)及無水甲苯(500 ml)裝入3頸1 L圓底燒瓶中。在氮氣氛下將反應混合物加熱至100℃歷時6小時。接著將反應混合物濃縮至乾燥且使其經歷管柱層析法以得到es17i-1
(5.65 g,39%)。
步驟2:es17i-2之合成
向es17i-1
(2.75 g,8.4 mmole)、碳酸氫鈉(1.4 g,16.7 mmole)於2-丙醇(75 ml)中之混合物中添加氯乙醛(50%水溶液,1.96 g)。
將反應混合物在75℃下加熱5小時之後,移除溶劑。將殘留物再溶解於二氯甲烷中且以水洗滌。將有機部分組合,經硫酸鈉乾燥,過濾且在真空下濃縮。藉由矽膠層析法使用己烷/乙酸乙酯(80/20)純化粗混合物得到純es17i-2
(2.52 g,85%)。
步驟3:es17i-3之合成
將es17i-2
(4.5 g,12.7 mmol)、4-第三丁基苯基酸(5.09 g,29 mmol)、碳酸鈉(9.22 g,87 mmol)、Pd(PPh)4
(0.99 g,0.86 mmol)、50 ml水及400 ml甲苯裝入3頸1 L圓底燒瓶中。在氮氣氛下將反應混合物加熱至100℃歷時17小時。將反應混合物以二氯甲烷稀釋且以鹽水洗滌。將有機部分組合,經硫酸鈉乾燥,過濾且在真空下濃縮。藉由矽膠層析法使用己烷/乙酸乙酯(80/20)純化粗混合物得到純es17i-3
(5.05 g,97%)。
步驟4
將es17i-3
(3.41 g,8.38 mmol)、Ir(acac)3
(821.24 mg,1.67 mmol)及30滴十三烷裝入25 ml 2頸燒瓶中。燒瓶為真空且重新填充氮3次且接著加熱至220℃歷時65小時。將反應混合物溶解於二氯甲烷中且使其經歷管柱層析法以獲得es17
(1 g,產率42%)。
步驟1:3-(三丁錫)-咪唑并[1,2-f]啡啶之合成
將咪唑并[1,2-f]啡啶(11.6 g,53.21 mmol)及600 mL無水THF裝入3頸圓底燒瓶中。在-78℃下將正丁基鋰溶液(環己烷中之2 M溶液,39.9 mL,79.8 mmol)添加至反應混合物中。在-78℃下攪拌2小時之後,在-78℃下添加三丁基氯化錫(25.97 g,79.8 mmol)。
將反應混合物在-78℃下攪拌兩小時。將反應混合物在真空下濃縮至乾燥且使其經歷管柱層析法(以三乙胺、己烷中之50% EtOAC預處理之矽膠)以獲得標題化合物(24.61 g,產率91%)。
步驟2:3-(2,6-二氯苯基)-咪唑并[1,2-f]啡啶之合成
將3-(三丁錫)-咪唑并[1,2-f]啡啶(23.87 g,47 mmol)、2,6-二氯碘苯(12.84 g,47.08 mmol)、PdCl2
(PPh3
)2
(1.97 g,2.82 mmol)及170 ml無水對二甲苯裝入250 ml圓底燒瓶中。在氮氣氛下將反應混合物加熱至120℃歷時17小時。將反應混合物以二氯甲烷稀釋且以飽和KF水溶液洗滌。濾去沉澱物且使濾液經歷管柱層析法(矽膠,二氯甲烷)以獲得標題化合物(10.35 g,產率60.8%)。
步驟3:3-(2,6-二苯基苯基)-咪唑并[1,2-f]啡啶之合成
將3-(2,6-二氯苯基)-咪唑并[1,2-f]啡啶(2.1 g,5.8 mmol)、苯基酸(2.828 g,23.4 mmol)、Pd(OAc)2
(1.127 g,5.02 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(4.11 g,10.03 mmol)、K3
PO4
及70 ml無水甲苯裝入200 ml圓底燒瓶中。在氮氣氛下將反應混合物加熱至100℃歷時22小時。將反應混合物濃縮至乾燥且使其經歷管柱層析法以獲得標題化合物(1.62 g,產率62%)。
步驟4
將3-(2,6-二苯基苯基)-咪唑并[1,2-f]啡啶(2.93 g,6.56 mmol)、Ir(ACAC)3
(0.643 g,1.31 mmol)及30滴十三烷裝入25 mL 2頸燒瓶中。燒瓶為真空且重新填充氮3次且接著加熱至220℃歷時65小時。將反應混合物溶解於二氯甲烷中且使其經歷管柱層析法以獲得es23
(560 g,產率28%)。
步驟1:2-(1H-苯并[d]咪唑-1-基)苯甲腈1
將苯并咪唑(2.00公克,16.9 mmol)溶解於30 mL無水二甲基甲醯胺中。向此混合物中添加氫化鈉(0.68公克,60%,16.9 mmol)。將此混合物在環境溫度下攪拌30 min,隨後添加1.80 mL(16.9 mmol)2-氟苯甲腈。將反應物在50℃下攪拌18小時,此後在冰水浴中將混合物冷卻且以100 mL水稀釋。以乙酸乙酯萃取產物。將有機層以水洗滌,經硫酸鈉乾燥且在真空中蒸發得到標題化合物。質譜及NMR資料認同結構。亦類似合成5,6-二甲基苯并咪唑類似物。
步驟2:2-(2-溴-1H-苯并[d]咪唑-1-基)苯甲腈2
將化合物1
(25.75公克,117.5 mmol)溶解於二噁烷(400 mL)中。向此混合物中添加N-溴代琥珀醯亞胺(20.91公克,117.5 mmol)。將此混合物在回流下攪拌3小時,此後將混合物傾入水中且以乙酸乙酯萃取產物。將有機層經硫酸鈉乾燥,在真空中濃縮且使用二氯甲烷-乙酸乙酯5:1(v/v)移動相層析(矽膠)得到標題化合物。由質譜及NMR資料確認結構。亦類似合成5,6-二甲基苯并咪唑類似物。
步驟3:3之合成
在20 mL無水四氫呋喃中攪拌化合物2
(4.86公克,16.3 mmol)。向此混合物中添加25 mL六甲基二矽氮烷鋰於四氫呋喃中之1 N溶液。將反應物在65℃下攪拌2.5小時。接著將反應混合物冷卻至環境溫度且以水中止。添加鹽酸水溶液(25 mL 1 N溶液)且將此混合物攪拌10分鐘,隨後以氫氧化銨水溶液中和。過濾收集所得棕色固體且在真空下乾燥。由質譜及NMR資料確認結構。
步驟4:4之合成
將化合物3
(2.15公克,9.18 mmol)置於200 mL圓底燒瓶中。向此混合物中添加1,2-二碘苯(1.20 mL,9.18 mmol)、碘化銅(0.52公克,2.75 mmol)、1,10-非啉(0.50公克,2.75 mmol)及碳酸鉀(2.66公克,19.28 mmol)。將燒瓶脫氣且重新填充氮氣,隨後添加40 mL無水二甲基甲醯胺。將反應物在150℃下攪拌18小時,隨後冷卻且傾入水中。過濾粗固體且使用二氯甲烷-甲醇19:1之移動相層析(矽膠)得到產物4
。LCMS 309.2(ES+
),309.2(AP+
);1
H NMR(CDCl3
)δ 8.75(m,2H),8.36(d,1H),8.15(d,1H),7.95(m,2H),7.81(m,1H),7.56(m,3H),7.44(m,2H)。
步驟5
將4
(0.6 g,1.945 mmol)、Ir(acac)3
(0.19 g,0.389 mmol)及30滴十三烷裝入25 mL 2頸燒瓶中。抽空燒瓶且重新填充氮氣3次且接著加熱至240℃歷時26 h。將所得混合物溶解於二氯甲烷中且使其經歷矽膠管柱層析法得到es101
,由質譜確認其結構。
在15 mL異丙醇中攪拌化合物3
(0.59公克,2.52 mmol)。向此混合物中添加碳酸氫鈉(0.42公克,5.04 mmol)及氯乙醛(0.50 mL 50%溶液,3.78 mmol)。將此混合物在回流下攪拌7小時,隨後冷卻,以水稀釋且以二氯甲烷萃取。使用管柱層析法(矽膠)以二氯甲烷-甲醇19:1溶離純化產物。LCMS 258.7(AP+
),259.3(ES+
);1
H NMR(DMSO d6
)δ 8.66(d,1H),8.55(m,1H),8.46(dd,1H),8.28(d,1H),7.84(m,2H),7.62(m,2H),7.47(m,2H)。
在75 mL無水二甲基甲醯胺中攪拌氫化鈉(8.65公克,60%,0.216 mol)。向此混合物中逐滴添加2,4-二甲基咪唑(20.75公克,0.216 mol)於100 mL DMF中之溶液。在環境溫度下攪拌1小時之後,逐滴添加2-氟苯甲腈(23.0 mL,0.216 mol)於75 mL DMF中之溶液。將此混合物在50℃下攪拌2小時且接著在環境溫度下攪拌16小時。接著將混合物傾入水中且以乙酸乙酯萃取產物。將有機層以水洗滌且經硫酸鈉乾燥。層析(矽膠)粗產物且以19:1二氯甲烷-甲醇,接著9:1二氯甲烷-甲醇溶離得到呈固體之產物。LCMS資料確認結構。
將化合物6
(5.18公克,26.0 mmol)溶解於乙腈(150 mL)中。向此混合物中添加N-溴代琥珀醯亞胺(4.67公克,26.0 mmol)。將此混合物在回流下攪拌1小時,隨後在真空中蒸發。將殘留物溶解於二氯甲烷中且以水洗滌。在真空中蒸發有機層得到呈黃色固體之標題化合物。NMR確認結構。
將化合物6
(6.82公克,34.5 mmol)分多份添加至冷卻至0℃之三氟乙酸酐(50 mL)中。15分鐘之後,以乾冰丙酮浴替代氯化鈉冰水浴且逐滴添加硝酸(6.0 mL 70%)。將此混合物攪拌至環境溫度歷時16小時,此後將其傾入冰水中且以固體碳酸氫鈉中和。以二氯甲烷萃取產物且在矽膠急驟管柱上使用49:1二氯甲烷-甲醇溶離純化得到呈橙色糊狀物之所需產物。LCMS資料支持結構。
將鄰胺苯甲腈(10.0公克,85.0 mmol)溶解於350 mL乙酸中。向此混合物中添加2,5-二甲氧基四氫呋喃(11.0公克,85.0 mmol)。將此混合物在回流下攪拌2小時,此後將反應混合物傾入水中且以二氯甲烷萃取產物。將有機層以水洗滌,經硫酸鈉乾燥且在矽膠管柱上使用1:1二氯甲烷-己烷移動相層析得到呈白色固體之標題化合物。NMR確認結構。
將化合物9
(12.07公克,72.0 mmol)溶解於250 mL無水二甲基甲醯胺中。將此混合物在冰水浴中冷卻。向此混合物中添加N-溴代琥珀醯亞胺(12.77公克,72.0 mmol)。將反應混合物在0℃下攪拌3小時,隨後傾入水中。以二氯甲烷萃取產物。將有機層以水洗滌,經硫酸鈉乾燥且在真空中濃縮。使用1:1二氯甲烷-己烷移動相管柱層析(矽膠)粗產物得到呈無色油狀物之化合物10
。NMR及LCMS資料確認結構。
步驟1
向1 L圓底燒瓶中添加7-溴咪唑并[1,2,-f]啡啶(10 g,33.89 mmol,經由通用程序製備)、哌啶(8.66 g,101 mmol)、乙酸鈀(532 mg,2.37 mmol)、二-第三丁基聯苯膦(1.41 g,4.74 mmol)、第三丁氧化鈉(4.56 g,47.45 mmol)及200 mL無水甲苯。將反應混合物加熱至100℃歷時14小時。冷卻之後,以氧化鋁管柱層析法純化反應混合物。產量:3.19 g。
步驟2
向1 L圓底燒瓶中添加7-哌啶-咪唑并[1,2-f]啡啶(2.9 g,33.89 mmol,自步驟1製備)及200 mL無水DMF。在室溫下在黑暗中伴隨攪拌向此混合物中逐滴添加100 mL N-溴代琥珀醯亞胺DMF溶液(1.79 g,10.08 mmol)。將反應混合物繼續攪拌隔夜。接著伴隨攪拌將混合物傾入1 L水中。過濾收集沉澱物,且進一步將其以大量水洗滌,且最終以MeOH(50 mL×2)洗滌,且接著乾燥。3-溴-7-亞哌啶基-咪唑并[1,2-f]啡啶之產量為3.5 g。
步驟3
向500 mL圓底燒瓶中添加3-溴-7-亞哌啶基-咪唑并[1,2-f]啡啶(3.5 g,9.2 mmol)、2,6-二甲苯基酸(8.28 g,55.2 mmol)、Pd2
(dba)3
(4.21 g,4.6 mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,7.55 g,18.40 mmol)、磷酸三鉀(15.6 g,73.6 mmol)及200 mL二甲苯。將反應物加熱至回流且在氮氣氛下攪拌84小時。冷卻之後,以矽膠管柱純化混合物。產量為2.25 g。
步驟4
將3-(2,6-二甲苯基)-7-亞哌啶基-咪唑并[1,2-f]啡啶(1.75 g,4.32 mmol)及參(乙醯丙酮)銥(III)(0.5 g,1 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到所需化合物(0.38 g)。
經由注射器向300 ml圓底燒瓶中添加6-氯咪唑并[1,2,-f]啡啶(5 g,19.78 mmol,自通用程序製備)、pd2
(dba)3
(1.08 g,1.18 mmol)、2-(二環己基)膦基聯苯(998 mg,2.84 mmol)、THF中之雙(三甲基矽烷基)醯胺鋰(23.75 ml,1 M,23.74 ml)。抽空反應燒瓶且重新填充氮氣。將反應混合物加熱至65℃隔夜。將反應物冷卻至室溫,添加1 M HCl水溶液(100 ml)且將反應物在室溫下攪拌5 min。接著藉由添加NaOH水溶液中和溶液。以二氯甲烷萃取水相3次。組合有機層,在真空中濃縮。藉由急驟層析法純化殘留物。產量為1.56 g。
步驟2
向100 ml圓底燒瓶中添加6-胺基-咪唑并[1,2,-f]啡啶(100 mg,0.42 mmol,自步驟1製備)、丁醛(61.84 mg,0.85 mmol)、三乙醯氧基硼氫化鈉(272 mg,1.28 mmol)及50 ml二氯甲烷。將反應混合物在室溫下攪拌隔夜。藉由添加飽和NaHCO3
水溶液中止反應混合物且以EtOAC萃取產物。濃縮EtOAC層而得到所需產物(140 mg)。
步驟4
將6-N,N-二異丙基-咪唑并[1,2-f]啡啶(0.45 g,1.14 mmol)及參(乙醯丙酮)銥(III)(0.138 g,0.28 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到所需化合物(0.1 g)。
向500 mL 2頸圓底燒瓶中放入2-溴-4-正己基苯胺(8.87公克,0.035 mol)、2-氰基苯基酸四甲基乙二醇酯(8.82公克,0.039 mol)、二氯雙(三苯基膦)鈀(II)(0.98公克,4%)及單水合磷酸三鉀(12.1公克,0.053 mol)。將燒瓶脫氣且重新填充氮氣,隨後經由注射器添加甲苯(120 mL)。將反應物在回流下攪拌3小時,此後將混合物冷卻至環境溫度。添加二氯甲烷(200 mL)且以水洗滌混合物。將有機層經硫酸鈉乾燥,在真空中濃縮且層析(矽膠)。以二氯甲烷-甲醇9:1 v/v溶離得到呈褐色固體之所需產物。NMR、MS確認結構。
向250 mL圓底燒瓶中放入2-己基啡啶-6-胺(6.17公克,0.022 mol)、2,4,6-三異丙苯基溴乙醛(7.93公克,0.024 mol,經由通用程序B製備)及其丙醇(50 mL)。將此混合物在回流下攪拌2小時,隨後添加碳酸氫鈉(3.7公克,0.044 mol)。將此混合物在回流下攪拌額外18小時。添加水(100 mL)及二氯甲烷(100 mL)。分離層。將有機層經硫酸鈉乾燥,在真空中濃縮且層析(矽膠)。以乙酸乙酯-二氯甲烷1:1 v/v溶離得到呈橙色油狀物之所需產物,使該產物靜置固化。1
H NMR(CDCl3
)δ8.72(d,1H),8.37(d,1H),7.64(m,2H),7.36(s,1H),7.19(m,1H),7.14(s,2H),7.00(d,1H),3.00(p,1H),2.69(t,2H),2.59(p,2H),1.36(d,6H),1.09(d,6H),0.93(d,6H),0.83(t,3H);GC MS 504。
將7-己基-3-(2,4,6-三異丙苯基)咪唑并[1,2-f]啡啶(3.9 g,7.72 mmol)及參(乙醯丙酮)銥(III)(0.757 g,1.54 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到所需化合物(0.732 g)。
向具備機械攪拌器、溫度計及加料漏斗之2 L 3頸燒瓶中添加300 g冰及300 mL H2
SO4
。向此混合物中逐滴添加200 mL CH3
CN中之2,6-二異丙基-4-溴苯胺(46.0 g,0.18 mol),同時將溫度維持在5℃下。接著逐滴添加180 mL冰冷水中之亞硝酸鈉(22.5 g,0.32 mol),同時將溫度維持在約0℃。在室溫下將所得澄清溶液緩慢傾入碘化鉀(105 g,0.63 mol)於300 ml水中之溶液中。將混合物攪拌1小時。在常規處理之後,在170℃下在真空下蒸餾粗產物得到冷卻後呈淺棕色軟固體之1-碘-2,6-二異丙基-4-溴苯(60 g)。
將1-碘-2,6-二異丙基-4-溴苯(17.6 g,0.048 mol)之150 mL無水甲苯溶液在-78℃下以n-BuLi(己烷中之1.6 M,75 mL)處理30分鐘。攪拌15分鐘之後,逐滴添加50 mL甲苯中之無水DMF(20 mL)。使所得混合物緩慢升溫至室溫。在常規處理之後,在140℃下在真空下蒸餾粗產物得到2,6-二異丙基-4-溴苯甲醛(11.5 g)。
在-78℃下將甲氧基甲基氯化三苯鏻(18.68 g,54.5 mmol)懸浮於200 mL THF中。逐滴添加雙(三甲基矽烷)胺基鋰(THF中之1.0 M,50 mL)。伴隨攪拌使所得混合物升溫至0℃。在將溶液冷卻至-78℃之後,逐滴添加20 mL THF中之2,6-二異丙基-4-溴苯甲醛(11.5 g,42.7 mmol)。使混合物緩慢升溫至室溫且繼續攪拌隔夜。在常規處理之後,在165℃下在真空下蒸餾粗產物得到2,6-二異丙基-4-溴-β-甲氧基苯乙烯(10 g)。將此產物溶解於20 mL二噁烷及100 mL 18% HCl溶液中且在100℃下回流6小時。在常規處理之後,在160℃下在真空下蒸餾粗產物得到2,6-二異丙基-4-溴苯基乙醛(7.5 g)。
在0℃下向2,6-二異丙基-4-溴苯基乙醛(7.3 g,25.8 mmol)之無水DMF溶液中添加2,6-二-第三丁基-4-甲基苯酚(0.056 g,0.26 mmol),繼而添加NBS(4.59 g,25.8 mmol)。在攪拌幾分鐘之後,添加苯磺酸(8.16 g,51.6 mmol)。在氮氣氛下將所得混合物在35℃下攪拌12 h。在常規處理之後,藉由管柱層析法純化粗產物得到2-(2,6-二異丙基-4-溴苯基)丙醛(5.4 g)。
向500 mL圓底燒瓶中添加上述中間體、2,3-二甲基-6-胺基啡啶(6.6 g,30 mmol)及100 mL NMP。將混合物在80℃下攪拌48小時。在常規處理之後,以矽膠管柱純化粗產物。在不同操作中產量為約1至2 g。
應保護以下程序之各步驟使其免受光照。將3-(2,6-二甲基-4-苯基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(1.90 g,4.46 mmol,經由通用方法B
繼而鈴木偶合(Suzuki coupling)自3-(2,6-二甲基-4-溴苯基)-6,7-二甲基咪唑并[1,2-f]啡啶獲得)及參(乙醯丙酮)銥(III)(0.48 g,0.99 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es32
(0.60 g)。1
H NMR結果確認所需化合物。發射λmax
=468,490 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.17,0.33)。
應保護以下程序之各步驟使其免受光照。將3-(2,6-二異丙苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(2.10 g,5.17 mmol,經由通用方法B
繼而以n-BuLi處理此THF溶液且在-78℃下以水中止而自3-(2,6-二異丙基-4-溴苯基)-6,7-二甲基咪唑并[1,2-f]啡啶獲得)及參(乙醯丙酮)銥(III)(0.56 g,1.15 mmol)裝入50 mL史蘭克支管燒瓶中。
將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es24
(0.54 g)。1
H NMR結果確認所需化合物。發射λmax
=458,488 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.17,0.25)。
應保護以下程序之各步驟使其免受光照。將3-(2,6-二異丙基-4-苯基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(1.75 g,3.60 mmol,經由通用方法B
繼而鈴木偶合(Suzuki coupling)自3-(2,6-二異丙基-4-溴苯基)-6,7-二甲基咪唑并[1,2-f]啡啶獲得)及參(乙醯丙酮)銥(III)(0.40 g,0.80 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es37
(0.54 g)。1
H NMR結果確認所需化合物。發射λmax
=456,488 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.17,0.24)。
應保護以下程序之各步驟使其免受光照。將3-(2,4,6-三異丙苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(1.95 g,4.35 mmol,藉由使用2,4,6-三異丙基苯甲醛作為起始材料自通用方法B
獲得)及參(乙醯丙酮)銥(III)(0.43 g,0.96 mmol)裝入50 mL史蘭克支管燒瓶中。將反應混合物在氮氣氛下攪拌且在沙浴中在240℃下加熱48小時。冷卻之後,將固化混合物溶解於CH2
Cl2
中且進一步以矽膠管柱純化得到es31
(0.52 g)。1
H NMR結果確認所需化合物。發射λmax
=460,490 nm(CH2
Cl2
溶液,在室溫下);CIE=(0.16,0.25)。
根據Lin等人在美國專利申請案第11/241,981號及Tung等人在美國專利申請案第11/242,025號中描述之程序製造包含es101
作為發射化合物之OLED裝置且當10 mA/cm2
電流穿過該裝置時其發射藍綠色光。
根據Lin等人在美國專利申請案第11/241,981號及Tung等人在美國專利申請案第11/242,025號中描述之程序製造包含本發明之摻雜劑之OLED裝置且該等裝置產生詳述於圖3-圖13、圖15及圖16中之資料。
儘管相關於特定實例及較佳實施例描述本發明,但本發明當然不受限於此等實例及實施例。因此,如熟習此項技術者所清楚,所主張之本發明包括本文所述之特定實例及較佳實施例之變體。
100...有機發光裝置
110...基板
115...陽極
120...電洞注入層
125...電洞傳遞層
130...電子阻擋層
135...發射層
140...電洞阻擋層
145...電子傳遞層
150...電子注入層
155...保護層
160...陰極
162...第一導電層
164...第二導電層
200...反向OLED裝置
210...基板
215...陰極
220...發射層
225...電洞傳遞層
230...陽極
圖1展示具有獨立電子傳遞層、電洞傳遞層及發射層以及其他層之有機發光裝置。
圖2展示不具有獨立電子傳遞層之反向有機發光裝置。
圖3展示包含化合物es1之裝置之IVL、光譜及壽命資料。
圖4展示包含化合物es6之裝置之IVL、光譜及壽命資料。
圖5展示包含化合物es8之裝置之IVL、光譜及壽命資料。
圖6展示包含化合物es9之裝置之IVL、光譜及壽命資料。
圖7展示包含化合物es13之裝置之IVL、光譜及壽命資料。
圖8展示包含化合物es14之裝置之IVL、光譜及壽命資料。
圖9展示包含化合物es16之裝置之IVL、光譜及壽命資料。
圖10展示包含化合物es17之裝置之IVL、光譜及壽命資料。
圖11展示包含化合物es19之裝置之IVL及光譜資料。
圖12展示包含化合物es20之裝置之IVL、光譜及壽命資料。
圖13展示包含化合物es4之裝置之IVL、光譜及壽命資料。
圖14展示es101在二氯甲烷溶液中之發射光譜。
圖15展示包含作為發射體之化合物es20及作為電洞注入層材料之HILx之裝置的IVL、光譜及壽命資料。
圖16展示包含作為發射體與電洞注入層材料之化合物es20之裝置的IVL、光譜及壽命資料。
圖17展示化合物HILx之結構。
Claims (39)
- 一種化合物,其包含磷光金屬錯合物,該錯合物包含選自組1之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;組1;
- 如請求項1之化合物,其中該金屬係選自由Re、Ru、Os、Rh、Ir、Pd、Pt及Au組成之群,且該雙牙配位體係 選自組2;組2;
- 如請求項2之化合物,其中該雙牙配位體具有式gs1-1。
- 如請求項1之化合物,其中該金屬為Ir或Pt且該雙牙配位體係選自組2。
- 如請求項1之化合物,其中該金屬錯合物為選自組2之配位體之均配Ir錯合物。
- 如請求項1之化合物,其中該金屬錯合物為混配Ir錯合物,其包含兩個選自組2之雙牙配位體及一第三單陰離子雙牙配位體。
- 如請求項6之化合物,其中該第三單陰離子雙牙配位體為乙醯丙酮根或經取代之乙醯丙酮根。
- 如請求項1之化合物,其中該金屬係選自由Re、Ru、Os、Rh、Ir、Pd、Pt及Au組成之群,且R1a-i 中之至少一者為2,6-二取代芳基。
- 如請求項1之化合物,其中該金屬係選自由Ir及Pt組成之群,該配位體具有式gs1-1且R1b 為2,6-二取代芳基。
- 如請求項9之化合物,其中該2,6-二取代芳基係選自由以下基團組成之群:2,6-二甲苯基、2,4,6-三甲苯基、2,6-二異丙苯基、2,4,6-三異丙苯基、2,6-二異丙基-4-苯基苯基、2,6-二甲基-4-苯基苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二苯基苯基、2,6-二苯基-4-異丙苯基、2,4,6-三苯基苯基、2,6-二異丙基-4-(4-異丙苯基)苯基、2,6-二異丙基-4-(3,5-二甲苯基)苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二異丙基-4-(吡啶-4-基)苯基及2,6-二-(3,5-二甲苯基)苯基。
- 一種化合物,其係選自組3,其中acac為乙醯丙酮根; 組3;
- 一種OLED裝置,其包含如請求項1或11之化合物中之任一者。
- 一種化合物,其包含磷光金屬錯合物,該錯合物包含選 自組4之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;組4;
- 如請求項13之化合物,其中該雙牙配位體係選自組5; 組5;
- 如請求項13之化合物,其中該雙牙配位體係選自組6;組6;
- 如請求項14之化合物,其中該雙牙配位體經一或多個2,6-二取代芳基或雜芳基取代。
- 如請求項16之化合物,其中該2,6-二取代芳基係選自由以下基團組成之群:2,6-二甲苯基、2,4,6-三甲苯基、2,6-二異丙苯基、2,4,6-三異丙苯基、2,6-二異丙基-4-苯基苯基、2,6-二甲基-4-苯基苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二苯基苯基、2,6-二苯基-4-異丙苯基、2,4,6-三苯基苯基、2,6-二異丙基-4-(4-異丙苯基)苯基、2,6-二異丙基-4-(3,5-二甲苯基)苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二異丙基-4-(吡 啶-4-基)苯基及2,6-二-(3,5-二甲苯基)苯基。
- 如請求項14之化合物,其中該金屬係選自由Re、Ru、Os、Rh、Ir、Pd、Pt及Au組成之群。
- 如請求項14之化合物,其中該金屬係選自由Os、Ir及Pt組成之群。
- 如請求項14之化合物,其中該金屬為Ir。
- 一種OLED裝置,其包含如請求項14之化合物。
- 一種化合物,其係對應於如請求項14之配位體,其中該金屬已由H置換。
- 一種化合物,其包含磷光金屬錯合物,該錯合物包含選自組7之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體包含碳烯供體且可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;組7;
- 如請求項23之化合物,其中該化合物係選自組8;組8;
- 一種OLED裝置,其包含如請求項23之化合物。
- 一種化合物,其包含磷光金屬錯合物,該錯合物包含選自組9之單陰離子雙牙配位體,其中該金屬係選自由原 子序大於40之非放射性金屬組成之群,且其中該雙牙配位體包含碳烯供體且可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體;組9;
- 如請求項26之化合物,其中該化合物係選自組10; 組10;
- 一種OLED裝置,其包含如請求項26之化合物。
- 一種化合物,其包含磷光金屬錯合物,該錯合物包含選自組11之單陰離子雙牙配位體,其中該金屬係選自由原子序大於40之非放射性金屬組成之群,且其中該雙牙配位體可與其他配位體連接以包含三牙、四牙、五牙或六牙配位體; 組11;
- 一種OLED裝置,其包含如請求項29之化合物。
- 一種化合物,其係對應於如請求項29之配位體,其中該金屬已由H置換。
- 一種化合物,其包含選自下列之金屬錯合物:
- 一種OLED裝置,其包含如請求項32之化合物。
- 如請求項1之化合物,其中該雙牙配位體係具下式:
- 如請求項1之化合物,其中該金屬錯合物為混配Ir錯合 物。
- 如請求項1之化合物,其中該金屬係選自由Ir及Pt組成之群,且該配位體係具如下之式gs1-1,及R1b 係2,6-二取代芳基:
- 如請求項36之化合物,其中該2,6-二取代芳基係選自由以下基團組成之群:2,6-二甲苯基、2,4,6-三甲苯基、2,6-二異丙苯基、2,4,6-三異丙苯基、2,6-二異丙基-4-苯基苯基、2,6-二甲基-4-苯基苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二苯基苯基、2,6-二苯基-4-異丙苯基、2,4,6-三苯基苯基、2,6-二異丙基-4-(4-異丙苯基)苯基、2,6-二異丙基-4-(3,5-二甲苯基)苯基、2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基、2,6-二異丙基-4-(吡啶-4-基)苯基及2,6-二-(3,5-二甲苯基)苯基。
- 如請求項13之化合物,其中該雙牙配位體係具下式:
- 如請求項38之化合物,其中該雙牙配位體係經一或多個2,6-二取代芳基或雜芳基取代。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI637955B (zh) * | 2007-06-20 | 2018-10-11 | 環球展覽公司 | 藍色磷光咪唑并啡啶材料 |
Families Citing this family (789)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9157023B2 (en) | 2003-11-18 | 2015-10-13 | Koninklijke Philips N.V. | Light-emitting device with an iridium complex |
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 |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
KR20160030582A (ko) | 2006-02-10 | 2016-03-18 | 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 |
US7816018B2 (en) * | 2006-11-21 | 2010-10-19 | Grace Semiconductor Manufacturing Corporation | Organic electroluminescent materials and organic electroluminescent device using the same |
JP2008147400A (ja) * | 2006-12-08 | 2008-06-26 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
EP2097938B1 (en) * | 2006-12-28 | 2019-07-17 | Universal Display Corporation | Long lifetime phosphorescent organic light emitting device (oled) structures |
US20130032785A1 (en) | 2011-08-01 | 2013-02-07 | Universal Display Corporation | Materials for organic light emitting diode |
US8431243B2 (en) | 2007-03-08 | 2013-04-30 | Universal Display Corporation | Phosphorescent materials containing iridium complexes |
US9130177B2 (en) | 2011-01-13 | 2015-09-08 | Universal Display Corporation | 5-substituted 2 phenylquinoline complexes materials for light emitting diode |
WO2008140069A1 (ja) * | 2007-05-16 | 2008-11-20 | Konica Minolta Holdings, Inc. | 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材料、表示装置及び照明装置 |
WO2008140115A1 (ja) * | 2007-05-16 | 2008-11-20 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5256484B2 (ja) * | 2007-05-16 | 2013-08-07 | 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材料、表示装置及び照明装置 |
WO2008142976A1 (ja) * | 2007-05-16 | 2008-11-27 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料 |
WO2008143059A1 (ja) * | 2007-05-16 | 2008-11-27 | Konica Minolta Holdings, Inc. | 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材料、表示装置及び照明装置 |
US20100141126A1 (en) * | 2007-05-16 | 2010-06-10 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display and illuminating device |
KR20160086983A (ko) | 2007-08-08 | 2016-07-20 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
KR20160104752A (ko) | 2007-08-08 | 2016-09-05 | 유니버셜 디스플레이 코포레이션 | 인광성 발광 다이오드의 단일 트리페닐렌 발색단 |
WO2009047993A1 (ja) * | 2007-10-13 | 2009-04-16 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
CN101896493B (zh) * | 2007-10-17 | 2015-04-08 | 巴斯夫欧洲公司 | 具有桥连碳烯配体的过渡金属配合物及其在oled中的用途 |
KR101642030B1 (ko) * | 2007-10-17 | 2016-07-25 | 바스프 에스이 | 가교된 카르벤 리간드를 포함하는 전이 금속 착물 및 이의 용도 |
US8476822B2 (en) | 2007-11-09 | 2013-07-02 | Universal Display Corporation | Saturated color organic light emitting devices |
WO2009061716A1 (en) * | 2007-11-09 | 2009-05-14 | Universal Display Corporation | Saturated color organic light emitting devices |
US8815411B2 (en) | 2007-11-09 | 2014-08-26 | The Regents Of The University Of Michigan | Stable blue phosphorescent organic light emitting devices |
WO2009073245A1 (en) | 2007-12-06 | 2009-06-11 | Universal Display Corporation | Light-emitting organometallic complexes |
US20090153034A1 (en) * | 2007-12-13 | 2009-06-18 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emittinig diodes |
US8221905B2 (en) * | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-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 |
RU2010137300A (ru) | 2008-02-22 | 2012-03-27 | Ф. Хоффманн-Ля Рош Аг (Ch) | Модуляторы бета-амилоида |
JP5304010B2 (ja) * | 2008-04-23 | 2013-10-02 | 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、表示装置及び照明装置 |
KR101656793B1 (ko) * | 2008-06-10 | 2016-09-12 | 유디씨 아일랜드 리미티드 | 신규한 전이 금속 착물 및 이의 유기 발광 다이오드에서의 용도 - ⅲ |
US20110114933A1 (en) * | 2008-06-10 | 2011-05-19 | Basf Se | Novel transition metal complexes and use thereof in organic light-emitting diodes - iv |
KR20160126093A (ko) * | 2008-06-10 | 2016-11-01 | 유디씨 아일랜드 리미티드 | 중수소화된 전이 금속 착물 및 이의 유기 발광 다이오드에서의 용도 ⅴ |
KR20110043581A (ko) | 2008-06-20 | 2011-04-27 | 바스프 에스이 | 환형 포스파젠 화합물 및 유기 발광 다이오드에서 이의 용도 |
CN102131767B (zh) | 2008-06-30 | 2013-08-21 | 通用显示公司 | 含有苯并菲的空穴传输材料 |
WO2010004887A1 (ja) * | 2008-07-07 | 2010-01-14 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料 |
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) |
DE102008033929A1 (de) * | 2008-07-18 | 2010-01-21 | Siemens Aktiengesellschaft | Phosphoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement |
JP5320881B2 (ja) * | 2008-07-23 | 2013-10-23 | 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、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料 |
JP5359088B2 (ja) * | 2008-07-24 | 2013-12-04 | 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、表示装置及び照明装置 |
JP5338184B2 (ja) * | 2008-08-06 | 2013-11-13 | 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、表示装置、照明装置 |
JP5621187B2 (ja) * | 2008-08-06 | 2014-11-05 | 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、表示装置、照明装置 |
US20100033082A1 (en) * | 2008-08-07 | 2010-02-11 | General Electric Company | Method of Manufacture of a Multi-Layer Phosphorescent Organic Light Emitting Device, and Articles Thereof |
WO2010027583A1 (en) | 2008-09-03 | 2010-03-11 | Universal Display Corporation | Phosphorescent materials |
EP2329544B1 (en) * | 2008-09-04 | 2017-05-17 | 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 |
JP5522046B2 (ja) * | 2008-09-17 | 2014-06-18 | 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、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料 |
JP5272608B2 (ja) * | 2008-09-20 | 2013-08-28 | 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、表示装置、及び照明装置 |
CN102160206B (zh) | 2008-09-25 | 2014-06-11 | 通用显示公司 | 有机硒物质及其在有机发光装置中的用途 |
KR101761236B1 (ko) | 2008-10-07 | 2017-07-25 | 오스람 오엘이디 게엠베하 | 축합환계로 치환된 실롤 및 유기전자소자에서의 그 용도 |
US8053770B2 (en) * | 2008-10-14 | 2011-11-08 | Universal Display Corporation | Emissive layer patterning for OLED |
KR101104546B1 (ko) * | 2008-11-03 | 2012-01-11 | 주식회사 엘지화학 | 새로운 함질소 헤테로환 화합물 및 이를 이용한 유기전자소자 |
EP2311826B1 (en) | 2008-11-03 | 2017-05-24 | LG Chem, Ltd. | Novel nitrogen-containing heterocyclic compound and organic electronic device using the same |
WO2010056669A1 (en) * | 2008-11-11 | 2010-05-20 | Universal Display Corporation | Phosphorescent emitters |
JP5629970B2 (ja) * | 2008-11-14 | 2014-11-26 | 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、表示装置及び照明装置 |
JP5412809B2 (ja) * | 2008-11-21 | 2014-02-12 | コニカミノルタ株式会社 | イミダゾール化合物の製造方法 |
WO2010064621A1 (ja) * | 2008-12-03 | 2010-06-10 | コニカミノルタホールディングス株式会社 | 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材料、表示装置及び照明装置 |
JP5515283B2 (ja) * | 2008-12-10 | 2014-06-11 | 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、表示装置及び照明装置 |
EP2377181B1 (en) | 2008-12-12 | 2019-05-01 | Universal Display Corporation | Improved 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 |
WO2010071030A1 (ja) * | 2008-12-19 | 2010-06-24 | コニカミノルタホールディングス株式会社 | 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材料、表示装置及び照明装置 |
US8420234B2 (en) * | 2009-01-06 | 2013-04-16 | Udc Ireland Limited | Organic electroluminescent device |
WO2010079678A1 (ja) * | 2009-01-09 | 2010-07-15 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
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 |
US8592806B2 (en) | 2009-02-26 | 2013-11-26 | Novaled Ag | Quinone compounds as dopants in organic electronics |
KR101398711B1 (ko) | 2009-02-27 | 2014-05-27 | 주식회사 엘지화학 | 질소 함유 복소환 화합물 및 이를 이용한 유기전자소자 |
EP2333862B1 (en) * | 2009-03-13 | 2014-09-17 | Mitsubishi Chemical Corporation | Process for manufacturing organic electroluminescent element |
JP5600884B2 (ja) * | 2009-03-17 | 2014-10-08 | 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、有機エレクトロルミネッセンス素子材料、表示装置及び照明装置 |
US11910700B2 (en) | 2009-03-23 | 2024-02-20 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
US8722205B2 (en) * | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
US8709615B2 (en) | 2011-07-28 | 2014-04-29 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
JP2010235708A (ja) * | 2009-03-30 | 2010-10-21 | Mitsubishi Chemicals Corp | 蛍光発光材料、有機電界発光素子用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
EP2417215B1 (en) | 2009-04-06 | 2014-05-07 | Universal Display Corporation | Metal complex comprising novel ligand structures |
JP5531446B2 (ja) * | 2009-04-20 | 2014-06-25 | 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材料、表示装置および照明装置 |
TWI609855B (zh) * | 2009-04-28 | 2018-01-01 | 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 |
JP5600891B2 (ja) * | 2009-05-15 | 2014-10-08 | 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、表示装置および照明装置 |
US8586203B2 (en) | 2009-05-20 | 2013-11-19 | Universal Display Corporation | Metal complexes with boron-nitrogen heterocycle containing ligands |
JP5568889B2 (ja) * | 2009-05-22 | 2014-08-13 | 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、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料 |
JP5629980B2 (ja) * | 2009-05-22 | 2014-11-26 | 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、表示装置及び照明装置 |
JP5499519B2 (ja) * | 2009-05-27 | 2014-05-21 | 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、表示装置及び照明装置 |
DE102009031683A1 (de) | 2009-07-03 | 2011-03-24 | Siemens Aktiengesellschaft | Phophoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement |
JP4523992B1 (ja) * | 2009-07-31 | 2010-08-11 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4758513B2 (ja) * | 2009-07-31 | 2011-08-31 | 富士フイルム株式会社 | 容器のスクリーニング方法 |
JP5577650B2 (ja) * | 2009-08-24 | 2014-08-27 | 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材料、表示装置及び照明装置 |
JP4474492B1 (ja) | 2009-08-31 | 2010-06-02 | 富士フイルム株式会社 | 有機電界発光素子用材料、及び有機電界発光素子 |
JP2010185068A (ja) | 2009-08-31 | 2010-08-26 | Fujifilm Corp | 有機電界発光素子 |
JP6219443B2 (ja) * | 2009-08-31 | 2017-10-25 | ユー・ディー・シー アイルランド リミテッド | 金属錯体化合物の製造方法及び有機電界発光素子 |
JP5926477B2 (ja) | 2009-08-31 | 2016-05-25 | ユー・ディー・シー アイルランド リミテッド | 金属錯体化合物の製造方法及び有機電界発光素子 |
JP4551480B1 (ja) * | 2009-08-31 | 2010-09-29 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4523990B1 (ja) * | 2009-08-31 | 2010-08-11 | 富士フイルム株式会社 | 有機電界発光素子用材料及び有機電界発光素子 |
JP5779318B2 (ja) | 2009-08-31 | 2015-09-16 | 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 |
JP4564588B1 (ja) | 2009-08-31 | 2010-10-20 | 富士フイルム株式会社 | 有機電界発光素子用材料、及び有機電界発光素子 |
JP4599469B1 (ja) * | 2009-08-31 | 2010-12-15 | 富士フイルム株式会社 | 有機電界発光素子用材料及び有機電界発光素子 |
JP5926785B2 (ja) * | 2009-09-30 | 2016-05-25 | 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 |
JP5627896B2 (ja) * | 2009-09-30 | 2014-11-19 | 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 |
DE102009049587A1 (de) | 2009-10-16 | 2011-04-21 | Merck Patent Gmbh | Metallkomplexe |
CN102741265B (zh) | 2009-10-28 | 2015-12-09 | 巴斯夫欧洲公司 | 杂配卡宾配合物及其在有机电子品中的用途 |
WO2011052516A1 (en) * | 2009-11-02 | 2011-05-05 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, display device, electronic device, and lighting device |
US8545996B2 (en) | 2009-11-02 | 2013-10-01 | The University Of Southern California | Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes |
US8580394B2 (en) | 2009-11-19 | 2013-11-12 | Universal Display Corporation | 3-coordinate copper(I)-carbene complexes |
JP5463897B2 (ja) * | 2009-12-18 | 2014-04-09 | 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材料、表示装置及び照明装置 |
EP2517278B1 (en) | 2009-12-22 | 2019-07-17 | Merck Patent GmbH | Electroluminescent formulations |
EP2517275B1 (en) | 2009-12-22 | 2018-11-07 | Merck Patent GmbH | Formulations comprising phase-separated functional materials |
WO2011076326A1 (en) | 2009-12-22 | 2011-06-30 | Merck Patent Gmbh | Electroluminescent functional surfactants |
JP6212098B2 (ja) * | 2010-01-15 | 2017-10-11 | 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 |
JP6014304B2 (ja) | 2010-01-15 | 2016-10-25 | 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 |
US8288187B2 (en) | 2010-01-20 | 2012-10-16 | Universal Display Corporation | Electroluminescent devices for lighting applications |
US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
US9156870B2 (en) * | 2010-02-25 | 2015-10-13 | Universal Display Corporation | Phosphorescent emitters |
US9175211B2 (en) * | 2010-03-03 | 2015-11-03 | Universal Display Corporation | Phosphorescent materials |
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 |
JP6246468B2 (ja) | 2010-03-11 | 2017-12-13 | メルク パテント ゲーエムベーハー | 治療および化粧品におけるファイバー |
US9005773B2 (en) | 2010-03-15 | 2015-04-14 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, display device, electronic device, and lighting device |
EP2550690B1 (en) | 2010-03-25 | 2018-12-26 | Universal Display Corporation | Solution processable doped triarylamine hole injection materials |
JP5724204B2 (ja) * | 2010-04-07 | 2015-05-27 | 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、表示装置、及び照明装置 |
US8968887B2 (en) | 2010-04-28 | 2015-03-03 | Universal Display Corporation | Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings |
US9520574B2 (en) * | 2010-04-28 | 2016-12-13 | Commonwealth Scientific And Industrial Research Organisation | Electroluminescent devices based on phosphorescent iridium and related group VIII metal multicyclic compounds |
CN103026521B (zh) | 2010-04-28 | 2016-11-09 | 通用显示公司 | 沉积预混合的材料 |
JP6312433B2 (ja) | 2010-05-27 | 2018-04-18 | メルク パテント ゲーエムベーハー | フォトルミネセント化合物を備えるアレイを具備する装置 |
US10190043B2 (en) | 2010-05-27 | 2019-01-29 | Merck Patent Gmbh | Compositions comprising quantum dots |
US8742657B2 (en) | 2010-06-11 | 2014-06-03 | Universal Display Corporation | Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications |
US8673458B2 (en) | 2010-06-11 | 2014-03-18 | Universal Display Corporation | Delayed fluorescence OLED |
JP6054290B2 (ja) * | 2010-06-15 | 2016-12-27 | メルク パテント ゲーエムベーハー | 金属錯体 |
EP2584019A4 (en) | 2010-06-17 | 2014-04-30 | Konica Minolta Holdings Inc | ORGANIC ELECTROLUMINESCENT MATERIAL, ORGANIC ELECTROLUMINESCENT ITEM, DISPLAY DEVICE AND LIGHTING DEVICE |
US9142792B2 (en) | 2010-06-18 | 2015-09-22 | Basf Se | Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide |
CN102947416B (zh) | 2010-06-18 | 2016-04-13 | 巴斯夫欧洲公司 | 包含二苯并呋喃化合物和8-羟基喹啉根合碱土金属或碱金属配合物的层的有机电子器件 |
CN102947415B (zh) | 2010-06-18 | 2016-01-06 | 巴斯夫欧洲公司 | 包含吡啶化合物和8-羟基喹啉根合碱土金属或碱金属配合物的层的有机电子器件 |
JP2012006878A (ja) * | 2010-06-25 | 2012-01-12 | Mitsubishi Chemicals Corp | 有機金属錯体、発光材料、有機電界発光素子材料、有機金属錯体含有組成物、有機電界発光素子、有機elディスプレイおよび有機el照明 |
DE102010027317A1 (de) * | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
DE102010027316A1 (de) * | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
JP5882318B2 (ja) | 2010-07-26 | 2016-03-09 | メルク パテント ゲーエムベーハー | デバイスにおけるナノ結晶 |
WO2012013272A1 (en) | 2010-07-26 | 2012-02-02 | Merck Patent Gmbh | Quantum dots and hosts |
WO2012016074A1 (en) | 2010-07-29 | 2012-02-02 | University Of Southern California | Co-deposition methods for the fabrication of organic optoelectronic devices |
CN103053043B (zh) | 2010-07-30 | 2016-03-16 | 默克专利有限公司 | 有机电致发光器件 |
KR101925158B1 (ko) | 2010-08-02 | 2018-12-04 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 트리아졸 유도체, 헤테로시클릭 화합물, 발광 엘리먼트, 발광 디바이스, 전자 디바이스 및 조명 디바이스 |
TW201223956A (en) * | 2010-08-13 | 2012-06-16 | Solvay | Light emitting materials for electronics |
EP2423214A1 (en) | 2010-08-13 | 2012-02-29 | Solvay SA | Light emitting materials for Electronics |
US9954180B2 (en) | 2010-08-20 | 2018-04-24 | Universal Display Corporation | Bicarbazole compounds for OLEDs |
EP2625171B1 (en) | 2010-10-07 | 2014-07-30 | Basf Se | Phenanthro[9,10-b]furans for electronic applications |
US9079872B2 (en) | 2010-10-07 | 2015-07-14 | Basf Se | Phenanthro[9, 10-B]furans for electronic applications |
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 |
US8269317B2 (en) | 2010-11-11 | 2012-09-18 | Universal Display Corporation | Phosphorescent materials |
US20120138906A1 (en) | 2010-12-07 | 2012-06-07 | The University of Southern California USC Stevens Institute for Innovation | Capture agents for unsaturated metal complexes |
US8362246B2 (en) | 2010-12-13 | 2013-01-29 | Basf Se | Bispyrimidines for electronic applications |
EP2651904B1 (en) | 2010-12-13 | 2014-11-12 | Basf Se | Bispyrimidines for electronic applications |
DE102010055901A1 (de) * | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
US10008677B2 (en) | 2011-01-13 | 2018-06-26 | Universal Display Corporation | Materials for organic light emitting diode |
US8415031B2 (en) | 2011-01-24 | 2013-04-09 | Universal Display Corporation | Electron transporting compounds |
WO2012110178A1 (en) | 2011-02-14 | 2012-08-23 | Merck Patent Gmbh | Device and method for treatment of cells and cell tissue |
US8748011B2 (en) | 2011-02-23 | 2014-06-10 | Universal Display Corporation | Ruthenium carbene complexes for OLED material |
US8563737B2 (en) | 2011-02-23 | 2013-10-22 | Universal Display Corporation | Methods of making bis-tridentate carbene complexes of ruthenium and osmium |
CN111732611B (zh) | 2011-02-23 | 2022-08-23 | 通用显示公司 | 新型的四齿铂络合物 |
US9005772B2 (en) | 2011-02-23 | 2015-04-14 | Universal Display Corporation | Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials |
US8492006B2 (en) | 2011-02-24 | 2013-07-23 | Universal Display Corporation | Germanium-containing red emitter materials for organic light emitting diode |
JP5747736B2 (ja) * | 2011-03-01 | 2015-07-15 | 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、表示装置及び照明装置 |
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 |
WO2012126566A1 (en) | 2011-03-24 | 2012-09-27 | Merck Patent Gmbh | Organic ionic functional materials |
EP2688889B1 (en) | 2011-03-25 | 2016-05-18 | Basf Se | 4h-imidazo[1,2-a]imidazoles for electronic applications |
US9806270B2 (en) | 2011-03-25 | 2017-10-31 | Udc Ireland Limited | 4H-imidazo[1,2-a]imidazoles for electronic applications |
US9155158B2 (en) | 2011-04-01 | 2015-10-06 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, display device, electronic device, and lighting device |
EP2694523B1 (de) | 2011-04-04 | 2017-01-11 | Merck Patent GmbH | Metallkomplexe |
US8580399B2 (en) | 2011-04-08 | 2013-11-12 | Universal Display Corporation | Substituted oligoazacarbazoles for light emitting diodes |
US8564192B2 (en) | 2011-05-11 | 2013-10-22 | Universal Display Corporation | Process for fabricating OLED lighting panels |
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 |
US9496502B2 (en) | 2011-05-12 | 2016-11-15 | Merck Patent Gmbh | Organic ionic compounds, compositions and electronic devices |
US9391288B2 (en) | 2011-05-12 | 2016-07-12 | Toray Industries, Inc. | Light emitting device material and light emitting device |
US8795850B2 (en) | 2011-05-19 | 2014-08-05 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology |
US9212197B2 (en) | 2011-05-19 | 2015-12-15 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants |
US8748012B2 (en) | 2011-05-25 | 2014-06-10 | Universal Display Corporation | Host materials for OLED |
US10158089B2 (en) | 2011-05-27 | 2018-12-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10079349B2 (en) | 2011-05-27 | 2018-09-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2012170461A1 (en) | 2011-06-08 | 2012-12-13 | Universal Display Corporation | Heteroleptic iridium carbene complexes and light emitting device using them |
KR101412437B1 (ko) | 2011-06-13 | 2014-06-26 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 전자 소자 |
US8884316B2 (en) | 2011-06-17 | 2014-11-11 | Universal Display Corporation | Non-common capping layer on an organic device |
US8659036B2 (en) | 2011-06-17 | 2014-02-25 | Universal Display Corporation | Fine tuning of emission spectra by combination of multiple emitter spectra |
WO2013000531A1 (de) | 2011-06-28 | 2013-01-03 | Merck Patent Gmbh | Metallkomplexe |
US9023420B2 (en) | 2011-07-14 | 2015-05-05 | Universal Display Corporation | Composite organic/inorganic layer for organic light-emitting devices |
US9252377B2 (en) | 2011-07-14 | 2016-02-02 | Universal Display Corporation | Inorganic hosts in OLEDs |
US9397310B2 (en) | 2011-07-14 | 2016-07-19 | Universal Display Corporation | Organice electroluminescent materials and devices |
US9783564B2 (en) | 2011-07-25 | 2017-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US8409729B2 (en) | 2011-07-28 | 2013-04-02 | Universal Display Corporation | Host materials for phosphorescent OLEDs |
US8926119B2 (en) | 2011-08-04 | 2015-01-06 | Universal Display Corporation | Extendable light source with variable light emitting area |
US8552420B2 (en) | 2011-08-09 | 2013-10-08 | Universal Display Corporation | OLED light panel with controlled brightness variation |
US9493698B2 (en) | 2011-08-31 | 2016-11-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN103814035A (zh) | 2011-09-12 | 2014-05-21 | 新日铁住金化学株式会社 | 具有含硅四元环构造的有机场致发光元件用材料及有机场致发光元件 |
KR101992874B1 (ko) | 2011-09-12 | 2019-06-26 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계 발광 소자 |
JP5914500B2 (ja) | 2011-09-12 | 2016-05-11 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
WO2013068376A1 (en) | 2011-11-10 | 2013-05-16 | Basf Se | 4h-imidazo[1,2-a]imidazoles for electronic applications |
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 |
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 |
KR101965292B1 (ko) | 2011-12-12 | 2019-04-04 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기전계발광 소자용 재료 및 그것을 사용한 유기전계발광 소자 |
US20130146875A1 (en) | 2011-12-13 | 2013-06-13 | Universal Display Corporation | Split electrode for organic devices |
US9461254B2 (en) | 2012-01-03 | 2016-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US8987451B2 (en) | 2012-01-03 | 2015-03-24 | Universal Display Corporation | Synthesis of cyclometallated platinum(II) complexes |
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 |
US10211413B2 (en) | 2012-01-17 | 2019-02-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2013113349A1 (en) | 2012-01-30 | 2013-08-08 | Merck Patent Gmbh | Nanocrystals on fibers |
JP5978843B2 (ja) | 2012-02-02 | 2016-08-24 | コニカミノルタ株式会社 | イリジウム錯体化合物、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、照明装置及び表示装置 |
US9118017B2 (en) | 2012-02-27 | 2015-08-25 | Universal Display Corporation | Host compounds for red phosphorescent OLEDs |
JP6140146B2 (ja) | 2012-03-12 | 2017-05-31 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
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 |
EP2834249A4 (en) | 2012-04-02 | 2015-11-04 | Du Pont | BLUE LUMINESCENT COMPOUNDS |
CN102643213B (zh) * | 2012-04-11 | 2014-04-09 | 暨明医药科技(苏州)有限公司 | 3,5-二甲基-4-溴甲基苯基腈的制备方法 |
US8723209B2 (en) | 2012-04-27 | 2014-05-13 | Universal Display Corporation | Out coupling layer containing particle polymer composite |
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 |
KR101640637B1 (ko) * | 2012-05-31 | 2016-07-18 | 주식회사 엘지화학 | 신규한 화합물, 그 제조 방법 및 상기 화합물을 이용한 유기 전자 소자 |
US9670404B2 (en) | 2012-06-06 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9502672B2 (en) | 2012-06-21 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP2869356B1 (en) | 2012-06-28 | 2016-10-12 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescence element and material for organic electroluminescence element |
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 |
WO2014009317A1 (en) | 2012-07-10 | 2014-01-16 | Basf Se | Benzimidazo[1,2-a]benzimidazole derivatives for electronic applications |
US20140014930A1 (en) * | 2012-07-13 | 2014-01-16 | Semiconductor Energy Laboratory Co., Ltd. | Organic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
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 |
JP6169078B2 (ja) | 2012-07-19 | 2017-07-26 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
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 |
US9540329B2 (en) | 2012-07-19 | 2017-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102095764B1 (ko) | 2012-07-25 | 2020-04-02 | 도레이 카부시키가이샤 | 발광 소자 재료 및 발광 소자 |
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 |
WO2014019710A1 (en) | 2012-08-02 | 2014-02-06 | Roche Diagnostics Gmbh | New bis-iridium-complexes for manufacturing of ecl-labels |
CN104769077B (zh) | 2012-08-02 | 2017-08-08 | 霍夫曼-拉罗奇有限公司 | 用于ecl的新型铱基配合物 |
ES2622998T3 (es) | 2012-08-02 | 2017-07-10 | F. Hoffmann-La Roche Ag | Nuevos complejos basados en iridio para EQL |
ES2625414T3 (es) | 2012-08-02 | 2017-07-19 | F. Hoffmann-La Roche Ag | Nuevos complejos basados en iridio para ECL |
EP2880123B1 (en) | 2012-08-02 | 2016-10-05 | Roche Diagnostics GmbH | New iridium-based complexes for ecl |
JP6146415B2 (ja) * | 2012-08-07 | 2017-06-14 | 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、照明装置及び表示装置 |
EP3424936B1 (de) | 2012-08-07 | 2021-04-07 | Merck Patent GmbH | Metallkomplexe |
US9978958B2 (en) * | 2012-08-24 | 2018-05-22 | Universal Display Corporation | Phosphorescent emitters with phenylimidazole ligands |
JP6217642B2 (ja) | 2012-08-24 | 2017-10-25 | コニカミノルタ株式会社 | 透明電極、電子デバイス、および透明電極の製造方法 |
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 |
EP3318566B1 (en) | 2012-09-20 | 2020-06-24 | UDC Ireland Limited | Azadibenzofurans for electronic applications |
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 |
TWI599570B (zh) | 2012-09-28 | 2017-09-21 | 新日鐵住金化學股份有限公司 | Compounds for organic electroluminescent devices and organic electroluminescent devices |
US9252363B2 (en) | 2012-10-04 | 2016-02-02 | Universal Display Corporation | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
JP5724987B2 (ja) * | 2012-10-31 | 2015-05-27 | 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、表示装置及び照明装置 |
WO2014072320A1 (en) | 2012-11-06 | 2014-05-15 | Basf Se | Phenoxasiline based compounds for electronic application |
US8692241B1 (en) | 2012-11-08 | 2014-04-08 | Universal Display Corporation | Transition metal complexes containing triazole and tetrazole carbene ligands |
US8946697B1 (en) | 2012-11-09 | 2015-02-03 | Universal Display Corporation | Iridium complexes with aza-benzo fused ligands |
US9748500B2 (en) | 2015-01-15 | 2017-08-29 | Universal Display Corporation | Organic light emitting materials |
US9685617B2 (en) | 2012-11-09 | 2017-06-20 | Universal Display Corporation | Organic electronuminescent materials and devices |
US9634264B2 (en) | 2012-11-09 | 2017-04-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9190623B2 (en) | 2012-11-20 | 2015-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10069090B2 (en) | 2012-11-20 | 2018-09-04 | 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 |
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 |
CN104885247B (zh) | 2012-12-17 | 2017-05-10 | 新日铁住金化学株式会社 | 有机电场发光元件 |
JP6363836B2 (ja) * | 2012-12-20 | 2018-07-25 | 株式会社半導体エネルギー研究所 | 発光素子 |
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 |
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 |
TWI609022B (zh) | 2013-03-20 | 2017-12-21 | Udc愛爾蘭責任有限公司 | 在有機發光二極體中作爲增效劑之氮雜苯并咪唑碳烯錯合物 |
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 |
JP6314599B2 (ja) | 2013-03-29 | 2018-04-25 | 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用化合物、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 |
US9537106B2 (en) | 2013-05-09 | 2017-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9735373B2 (en) | 2013-06-10 | 2017-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
WO2015000955A1 (en) | 2013-07-02 | 2015-01-08 | Basf Se | Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes |
US10121975B2 (en) | 2013-07-03 | 2018-11-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9761807B2 (en) | 2013-07-15 | 2017-09-12 | Universal Display Corporation | Organic light emitting diode materials |
US9553274B2 (en) | 2013-07-16 | 2017-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9324949B2 (en) | 2013-07-16 | 2016-04-26 | 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 |
JP2016525781A (ja) | 2013-07-29 | 2016-08-25 | 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Merck Patent GmbH | 電気光学素子およびその使用 |
EP3028319A1 (de) | 2013-07-29 | 2016-06-08 | Merck Patent GmbH | Elekrolumineszenzvorrichtung |
WO2015014835A1 (en) | 2013-07-31 | 2015-02-05 | Basf Se | Luminescent diazabenzimidazole carbene metal complexes |
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 |
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 |
KR102218122B1 (ko) * | 2013-09-11 | 2021-02-19 | 메르크 파텐트 게엠베하 | 금속 착물 |
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 |
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 |
EP3063153B1 (en) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophenes for electronic applications |
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 |
US10033000B2 (en) | 2013-11-15 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10056565B2 (en) | 2013-11-20 | 2018-08-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102153039B1 (ko) | 2013-11-28 | 2020-09-07 | 삼성전자주식회사 | 카바졸계 화합물 및 이를 포함한 유기 발광 소자 |
GB2520738B (en) * | 2013-11-29 | 2018-08-08 | Cambridge Display Tech Ltd | Phosphorescent metal complex dendrimers containing an imidazo[1,2-f]phenanthridine ligand |
US10644251B2 (en) | 2013-12-04 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9876173B2 (en) | 2013-12-09 | 2018-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10355227B2 (en) | 2013-12-16 | 2019-07-16 | Universal Display Corporation | Metal complex for phosphorescent OLED |
CN105993083B (zh) | 2013-12-20 | 2018-07-03 | Udc 爱尔兰有限责任公司 | 具有极短衰变时间的高效oled装置 |
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 |
KR101833656B1 (ko) | 2014-01-10 | 2018-02-28 | 내셔날 인스티튜트 오브 어드밴스드 인더스트리얼 사이언스 앤드 테크놀로지 | 시클로메탈화 이리듐 착체의 원료 및 제조 방법 |
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 |
WO2015125986A1 (ko) * | 2014-02-20 | 2015-08-27 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
US10707423B2 (en) | 2014-02-21 | 2020-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9502656B2 (en) | 2014-02-24 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9647217B2 (en) | 2014-02-24 | 2017-05-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10403825B2 (en) | 2014-02-27 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9181270B2 (en) | 2014-02-28 | 2015-11-10 | Universal Display Corporation | Method of making sulfide compounds |
US9673407B2 (en) | 2014-02-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
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 |
KR102330660B1 (ko) | 2014-03-31 | 2021-11-24 | 유디씨 아일랜드 리미티드 | o-치환된 비-사이클로메탈화 아릴 그룹을 갖는 카르벤 리간드를 포함하는 금속 착체 및 유기 발광 다이오드에서의 이의 용도 |
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 |
US9847498B2 (en) * | 2014-04-14 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10008679B2 (en) * | 2014-04-14 | 2018-06-26 | 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 |
US10457699B2 (en) | 2014-05-02 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN106463619B (zh) * | 2014-05-08 | 2020-07-07 | 环球展览公司 | 稳定的咪唑并菲啶材料 |
US10636983B2 (en) | 2014-05-08 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10301338B2 (en) | 2014-05-08 | 2019-05-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10403830B2 (en) * | 2014-05-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9997716B2 (en) | 2014-05-27 | 2018-06-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10461260B2 (en) | 2014-06-03 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9911931B2 (en) * | 2014-06-26 | 2018-03-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10297762B2 (en) | 2014-07-09 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102304718B1 (ko) * | 2014-07-10 | 2021-09-27 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US10566546B2 (en) | 2014-07-14 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9929357B2 (en) | 2014-07-22 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672995B2 (en) * | 2014-07-24 | 2020-06-02 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
WO2016016791A1 (en) | 2014-07-28 | 2016-02-04 | Idemitsu Kosan Co., Ltd (Ikc) | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
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 |
EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
US10749113B2 (en) | 2014-09-29 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10135007B2 (en) | 2014-09-29 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10043987B2 (en) | 2014-09-29 | 2018-08-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
US10868261B2 (en) | 2014-11-10 | 2020-12-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10411201B2 (en) | 2014-11-12 | 2019-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10038151B2 (en) | 2014-11-12 | 2018-07-31 | 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 |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
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 |
EP3229288B1 (en) | 2014-12-04 | 2019-05-01 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Polymer, and mixture, formulation and organic electronic device containing the same, and monomer thereof |
US10323180B2 (en) | 2014-12-04 | 2019-06-18 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Deuterated organic compound, mixture and composition containing said compound, and organic electronic device |
WO2016091219A1 (zh) | 2014-12-11 | 2016-06-16 | 广州华睿光电材料有限公司 | 有机化合物、包含其的混合物、组合物和有机电子器件 |
EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
US9450195B2 (en) | 2014-12-17 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10253252B2 (en) | 2014-12-30 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10636978B2 (en) | 2014-12-30 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
CN107108862B (zh) | 2015-01-13 | 2019-08-02 | 广州华睿光电材料有限公司 | 含乙炔基交联基团的共轭聚合物、包含其的混合物、组合物、有机电子器件及其应用 |
US9711730B2 (en) | 2015-01-25 | 2017-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418569B2 (en) | 2015-01-25 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
US10355222B2 (en) | 2015-02-06 | 2019-07-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
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 |
EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
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 |
CN107406471B (zh) | 2015-03-05 | 2020-06-02 | 株式会社Lg化学 | 杂环化合物和包含其的有机发光元件 |
US10686143B2 (en) | 2015-03-05 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10700289B2 (en) | 2015-03-05 | 2020-06-30 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting element comprising same |
US10270046B2 (en) | 2015-03-06 | 2019-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9780316B2 (en) | 2015-03-16 | 2017-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
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 |
EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
US10297770B2 (en) | 2015-03-27 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10693082B2 (en) | 2015-04-06 | 2020-06-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102584846B1 (ko) * | 2015-05-05 | 2023-10-04 | 유니버셜 디스플레이 코포레이션 | 유기 전계발광 재료 및 디바이스 |
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 |
US10109799B2 (en) | 2015-05-21 | 2018-10-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10256411B2 (en) | 2015-05-21 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10033004B2 (en) | 2015-06-01 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2016193243A1 (en) | 2015-06-03 | 2016-12-08 | Udc Ireland Limited | Highly efficient oled devices with very short decay times |
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 |
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 |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11018309B2 (en) | 2015-08-03 | 2021-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US10672996B2 (en) | 2015-09-03 | 2020-06-02 | 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 |
KR102500272B1 (ko) | 2015-09-16 | 2023-02-16 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 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 |
EP3356368B1 (en) | 2015-10-01 | 2021-07-21 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
US10593892B2 (en) | 2015-10-01 | 2020-03-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
US10847728B2 (en) | 2015-10-01 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180269407A1 (en) | 2015-10-01 | 2018-09-20 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
US10991895B2 (en) | 2015-10-06 | 2021-04-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
KR20180079328A (ko) | 2015-11-04 | 2018-07-10 | 이데미쓰 고산 가부시키가이샤 | 벤즈이미다졸 축합 헤테로아릴 |
WO2017080326A1 (zh) | 2015-11-12 | 2017-05-18 | 广州华睿光电材料有限公司 | 印刷组合物、包含其的电子器件及功能材料薄膜的制备方法 |
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 |
US11174258B2 (en) | 2015-12-04 | 2021-11-16 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
US10968243B2 (en) | 2015-12-04 | 2021-04-06 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organometallic complex and application thereof in electronic devices |
US20190006601A1 (en) | 2015-12-21 | 2019-01-03 | Idemitsu Kosan Co., Ltd. | Nitrogen-containing heterocyclic compounds and organic electroluminescence devices containing them |
US10957861B2 (en) | 2015-12-29 | 2021-03-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11024808B2 (en) | 2015-12-29 | 2021-06-01 | 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 |
DE112016006231T5 (de) | 2016-01-14 | 2018-10-18 | National Institute Of Advanced Industrial Science And Technology | Verfahren zum Herstellen eines cyclometallierten Iridiumkomplexes |
US10457864B2 (en) | 2016-02-09 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US10600967B2 (en) | 2016-02-18 | 2020-03-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11094891B2 (en) | 2016-03-16 | 2021-08-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
TW201802075A (zh) * | 2016-03-18 | 2018-01-16 | 陶氏全球科技責任有限公司 | 菲并喹唑啉核化合物 |
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 |
WO2017178864A1 (en) | 2016-04-12 | 2017-10-19 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
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 |
US11228002B2 (en) | 2016-04-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11081647B2 (en) | 2016-04-22 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20170324049A1 (en) | 2016-05-05 | 2017-11-09 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
US10985328B2 (en) | 2016-05-25 | 2021-04-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10468609B2 (en) | 2016-06-02 | 2019-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862054B2 (en) | 2016-06-20 | 2020-12-08 | 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 |
US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10651403B2 (en) | 2016-06-20 | 2020-05-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2017221999A1 (en) | 2016-06-22 | 2017-12-28 | Idemitsu Kosan Co., Ltd. | Specifically substituted benzofuro- and benzothienoquinolines for organic light emitting diodes |
US10957866B2 (en) | 2016-06-30 | 2021-03-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
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 |
US20180039249A1 (en) * | 2016-08-02 | 2018-02-08 | General Electric Company | Automated dynamical control of operations and design of physical systems through time |
US10205105B2 (en) | 2016-08-15 | 2019-02-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11183642B2 (en) | 2016-10-03 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11081658B2 (en) | 2016-10-03 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11127906B2 (en) | 2016-10-03 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11189804B2 (en) | 2016-10-03 | 2021-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US10236458B2 (en) | 2016-10-24 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US10662196B2 (en) | 2016-11-17 | 2020-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10964893B2 (en) | 2016-11-17 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10833276B2 (en) | 2016-11-21 | 2020-11-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10153445B2 (en) | 2016-11-21 | 2018-12-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN109790459B (zh) | 2016-11-23 | 2022-08-12 | 广州华睿光电材料有限公司 | 有机化合物 |
CN109790460B (zh) | 2016-11-23 | 2023-10-13 | 广州华睿光电材料有限公司 | 含硼有机化合物及应用、有机混合物、有机电子器件 |
WO2018095392A1 (zh) | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | 有机混合物、组合物以及有机电子器件 |
WO2018095379A1 (zh) | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | 金属有机配合物、高聚物、组合物及有机电子器件 |
EP3546532B1 (en) | 2016-11-23 | 2021-06-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Printing ink composition, preparation method therefor, and uses thereof |
CN109791992B (zh) | 2016-11-23 | 2021-07-23 | 广州华睿光电材料有限公司 | 高聚物、包含其的混合物、组合物和有机电子器件以及用于聚合的单体 |
WO2018095389A1 (zh) | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | 含氮稠杂环的化合物及其应用 |
US11555048B2 (en) | 2016-12-01 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN109790461B (zh) | 2016-12-08 | 2022-08-12 | 广州华睿光电材料有限公司 | 混合物、组合物及有机电子器件 |
CN109790118A (zh) | 2016-12-13 | 2019-05-21 | 广州华睿光电材料有限公司 | 共轭聚合物及其在有机电子器件的应用 |
US11545636B2 (en) | 2016-12-15 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11548905B2 (en) | 2016-12-15 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10490753B2 (en) | 2016-12-15 | 2019-11-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10811618B2 (en) | 2016-12-19 | 2020-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN106784401A (zh) * | 2016-12-21 | 2017-05-31 | 武汉华星光电技术有限公司 | 有机发光器件及其制作方法 |
US11289654B2 (en) | 2016-12-22 | 2022-03-29 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Polymers containing furanyl crosslinkable groups and uses thereof |
CN109792003B (zh) | 2016-12-22 | 2020-10-16 | 广州华睿光电材料有限公司 | 基于狄尔斯-阿尔德反应的可交联聚合物及其在有机电子器件中的应用 |
US11152579B2 (en) | 2016-12-28 | 2021-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11201298B2 (en) | 2017-01-09 | 2021-12-14 | 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 |
US12089486B2 (en) | 2017-02-08 | 2024-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US10745431B2 (en) | 2017-03-08 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3372611B1 (en) | 2017-03-08 | 2020-06-24 | Samsung Electronics Co., Ltd. | Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound |
US10741780B2 (en) | 2017-03-10 | 2020-08-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672998B2 (en) | 2017-03-23 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10873037B2 (en) | 2017-03-28 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10910577B2 (en) | 2017-03-28 | 2021-02-02 | 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 |
US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862046B2 (en) | 2017-03-30 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11276829B2 (en) | 2017-03-31 | 2022-03-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11139443B2 (en) | 2017-03-31 | 2021-10-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US11084838B2 (en) | 2017-04-21 | 2021-08-10 | Universal Display Corporation | Organic electroluminescent materials and device |
US11101434B2 (en) | 2017-04-21 | 2021-08-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10975113B2 (en) | 2017-04-21 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
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 |
US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10822362B2 (en) | 2017-05-11 | 2020-11-03 | 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 |
US10930862B2 (en) | 2017-06-01 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11832510B2 (en) | 2017-06-23 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10968226B2 (en) | 2017-06-23 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11725022B2 (en) | 2017-06-23 | 2023-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11758804B2 (en) | 2017-06-23 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11608321B2 (en) | 2017-06-23 | 2023-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11678565B2 (en) | 2017-06-23 | 2023-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11495757B2 (en) | 2017-06-23 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN109111486A (zh) | 2017-06-23 | 2019-01-01 | 环球展览公司 | 有机电致发光材料和装置 |
US11814403B2 (en) | 2017-06-23 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11802136B2 (en) | 2017-06-23 | 2023-10-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11552261B2 (en) | 2017-06-23 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11174259B2 (en) | 2017-06-23 | 2021-11-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11469382B2 (en) | 2017-07-12 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11322691B2 (en) | 2017-07-26 | 2022-05-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11239433B2 (en) | 2017-07-26 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11765970B2 (en) | 2017-07-26 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11917843B2 (en) | 2017-07-26 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11968883B2 (en) | 2017-07-26 | 2024-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11678499B2 (en) | 2017-07-27 | 2023-06-13 | Universal Display Corporation | Use of singlet-triplet gap hosts for increasing stability of blue phosphorescent emission |
US11744141B2 (en) | 2017-08-09 | 2023-08-29 | 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 |
US11910699B2 (en) | 2017-08-10 | 2024-02-20 | 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 |
US11696492B2 (en) | 2017-09-07 | 2023-07-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11444249B2 (en) | 2017-09-07 | 2022-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11424420B2 (en) | 2017-09-07 | 2022-08-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10608188B2 (en) | 2017-09-11 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11778897B2 (en) | 2017-09-20 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3466954A1 (en) | 2017-10-04 | 2019-04-10 | Idemitsu Kosan Co., Ltd. | Fused phenylquinazolines bridged with a heteroatom |
US11214587B2 (en) | 2017-11-07 | 2022-01-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11183646B2 (en) | 2017-11-07 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11910702B2 (en) | 2017-11-07 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent devices |
US11168103B2 (en) | 2017-11-17 | 2021-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US11404651B2 (en) | 2017-12-14 | 2022-08-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex material and application thereof in electronic devices |
US12075690B2 (en) | 2017-12-14 | 2024-08-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11233204B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11233205B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2019114764A1 (zh) | 2017-12-14 | 2019-06-20 | 广州华睿光电材料有限公司 | 一种有机金属配合物,包含其的聚合物、混合物和组合物,及其在电子器件中的应用 |
US11674080B2 (en) | 2017-12-14 | 2023-06-13 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex, polymer, mixture, formulation and use thereof |
US10971687B2 (en) | 2017-12-14 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2019120263A1 (zh) | 2017-12-21 | 2019-06-27 | 广州华睿光电材料有限公司 | 有机混合物及其在有机电子器件中的应用 |
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 |
US11515493B2 (en) | 2018-01-11 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11271177B2 (en) | 2018-01-11 | 2022-03-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102637103B1 (ko) * | 2018-01-23 | 2024-02-20 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물 |
US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11367840B2 (en) | 2018-01-26 | 2022-06-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11845764B2 (en) | 2018-01-26 | 2023-12-19 | 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 |
US11342509B2 (en) | 2018-02-09 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11180519B2 (en) | 2018-02-09 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11239434B2 (en) | 2018-02-09 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11957050B2 (en) | 2018-02-09 | 2024-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
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 |
US11217757B2 (en) | 2018-03-12 | 2022-01-04 | Universal Display Corporation | Host materials for electroluminescent devices |
JPWO2019181465A1 (ja) | 2018-03-19 | 2021-04-30 | 日鉄ケミカル&マテリアル株式会社 | 有機電界発光素子 |
US11882759B2 (en) | 2018-04-13 | 2024-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11616203B2 (en) | 2018-04-17 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11342513B2 (en) | 2018-05-04 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11515494B2 (en) | 2018-05-04 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11753427B2 (en) | 2018-05-04 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11793073B2 (en) | 2018-05-06 | 2023-10-17 | Universal Display Corporation | Host materials for electroluminescent devices |
US11459349B2 (en) | 2018-05-25 | 2022-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11450822B2 (en) | 2018-05-25 | 2022-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11716900B2 (en) | 2018-05-30 | 2023-08-01 | Universal Display Corporation | Host materials for electroluminescent devices |
US11296283B2 (en) | 2018-06-04 | 2022-04-05 | 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 |
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 |
US11753425B2 (en) | 2018-07-11 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3604477A1 (en) | 2018-07-30 | 2020-02-05 | Idemitsu Kosan Co., Ltd. | Polycyclic compound, organic electroluminescence device, and electronic device |
EP3608319A1 (en) | 2018-08-07 | 2020-02-12 | Idemitsu Kosan Co., Ltd. | Condensed aza cycles as organic light emitting device and materials for use in same |
US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
WO2020053150A1 (en) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TW202030902A (zh) | 2018-09-12 | 2020-08-16 | 德商麥克專利有限公司 | 電致發光裝置 |
TWI826522B (zh) | 2018-09-12 | 2023-12-21 | 德商麥克專利有限公司 | 電致發光裝置 |
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 |
US11495752B2 (en) | 2018-10-08 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11469383B2 (en) | 2018-10-08 | 2022-10-11 | 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 |
US11469384B2 (en) | 2018-11-02 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US11889708B2 (en) | 2019-11-14 | 2024-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11672165B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11706980B2 (en) | 2018-11-28 | 2023-07-18 | Universal Display Corporation | Host materials for electroluminescent devices |
US11672176B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Host materials for electroluminescent devices |
US11690285B2 (en) | 2018-11-28 | 2023-06-27 | Universal Display Corporation | Electroluminescent devices |
US11716899B2 (en) | 2018-11-28 | 2023-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11623936B2 (en) | 2018-12-11 | 2023-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for 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 |
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 |
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 |
US11637261B2 (en) | 2019-03-12 | 2023-04-25 | Universal Display Corporation | Nanopatch antenna outcoupling structure for use in OLEDs |
US11569480B2 (en) | 2019-03-12 | 2023-01-31 | Universal Display Corporation | Plasmonic OLEDs and vertical dipole emitters |
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 |
US11963438B2 (en) | 2019-03-26 | 2024-04-16 | The University Of Southern California | Organic electroluminescent materials and devices |
KR20210151882A (ko) | 2019-04-11 | 2021-12-14 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
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 |
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 |
CN110534650B (zh) * | 2019-05-28 | 2021-08-10 | 华南理工大学 | 一种自滤光窄光谱响应有机光探测器 |
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 |
US11926638B2 (en) | 2019-07-22 | 2024-03-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11685754B2 (en) | 2019-07-22 | 2023-06-27 | Universal Display Corporation | Heteroleptic organic electroluminescent materials |
KR20210014813A (ko) | 2019-07-30 | 2021-02-10 | 삼성디스플레이 주식회사 | 표시장치 |
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 |
US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11925105B2 (en) | 2019-08-26 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US11820783B2 (en) | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
US11919914B2 (en) | 2019-10-25 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11765965B2 (en) | 2019-10-30 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20220092590A (ko) | 2019-11-04 | 2022-07-01 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
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 |
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 |
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 |
US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11917900B2 (en) | 2020-01-28 | 2024-02-27 | 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 |
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 |
KR20230002860A (ko) | 2020-04-21 | 2023-01-05 | 메르크 파텐트 게엠베하 | 유기 기능성 재료를 포함하는 에멀젼 |
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 |
KR20210153245A (ko) | 2020-06-10 | 2021-12-17 | 박문석 | 압전소자의 진동에너지 흡수효율 증진을 위한 혼합조성물 |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US12065451B2 (en) | 2020-08-19 | 2024-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240049492A1 (en) | 2020-09-18 | 2024-02-08 | Samsung Display Co., Ltd. | Organic electroluminescent device |
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 |
US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
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 |
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 |
US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
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 |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4231804A3 (en) | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
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 |
US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240188316A1 (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 |
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 |
US20240188419A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
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 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005049762A1 (en) * | 2003-11-18 | 2005-06-02 | Philips Intellectual Property & Standards Gmbh | Light-emitting device with an iridium complex |
JP2005298483A (ja) * | 2004-03-17 | 2005-10-27 | National Institute Of Advanced Industrial & Technology | イリジウム錯体およびこれを用いた発光材料 |
WO2005113704A2 (en) * | 2004-05-18 | 2005-12-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
Family Cites Families (190)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB633158A (en) * | 1946-07-06 | 1949-12-12 | Du Pont | Improvements in or relating to photographic sensitising dyes and intermediates |
US3707745A (en) | 1970-12-16 | 1973-01-02 | Phillips Petroleum Co | Yarn texturing |
SU691450A1 (ru) * | 1977-04-04 | 1979-10-15 | Ростовский Ордена Трудового Красного Знамени Государственный Университет | Производные 2 фенилфенатр-(9,10)оксазола в качестве люминофоров |
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
US5336674A (en) * | 1993-01-27 | 1994-08-09 | Merck & Co., Inc. | 2-phenanthridinyl carbaphenem antibacterial agent |
DE69412567T2 (de) | 1993-11-01 | 1999-02-04 | Hodogaya Chemical Co., Ltd., Tokio/Tokyo | Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US6548956B2 (en) | 1994-12-13 | 2003-04-15 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
JP2000516761A (ja) | 1996-08-12 | 2000-12-12 | ザ トラスティーズ オブ プリンストン ユニバーシティ | 非ポリマー可撓性有機発光デバイス |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
GB9822963D0 (en) | 1998-10-20 | 1998-12-16 | Agner Erik | Improvements in or relating to chromatography |
US6310360B1 (en) | 1999-07-21 | 2001-10-30 | The Trustees Of Princeton University | Intersystem crossing agents for efficient utilization of excitons in organic light emitting devices |
US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
DE60045110D1 (de) † | 1999-12-01 | 2010-11-25 | Univ Princeton | Erungsmittel in organischen led's |
KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
US6565994B2 (en) | 2000-02-10 | 2003-05-20 | Fuji Photo Film Co., Ltd. | Light emitting device material comprising iridium complex and light emitting device using same material |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
JP2002050860A (ja) | 2000-08-04 | 2002-02-15 | Toray Eng Co Ltd | 実装方法および実装装置 |
WO2002015645A1 (en) | 2000-08-11 | 2002-02-21 | The Trustees Of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorescence |
US6939624B2 (en) | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
EP2276084A1 (en) | 2001-03-14 | 2011-01-19 | The Trustees of Princeton University | Materials and devices for blue phosphorescence based organic light emitting diodes |
JP3650082B2 (ja) | 2001-06-04 | 2005-05-18 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子、発光材料および有機化合物 |
JP4310077B2 (ja) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
ATE431970T1 (de) | 2001-06-20 | 2009-06-15 | Showa Denko Kk | Licht emittierendes material und organische leuchtdiode |
US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
US7431968B1 (en) * | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
US6878975B2 (en) | 2002-02-08 | 2005-04-12 | Agilent Technologies, Inc. | Polarization field enhanced tunnel structures |
JP2003253129A (ja) † | 2002-02-28 | 2003-09-10 | Jsr Corp | 発光性組成物 |
JP3919583B2 (ja) | 2002-04-12 | 2007-05-30 | キヤノン株式会社 | 有機発光素子 |
US20030230980A1 (en) | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
JP4193523B2 (ja) * | 2002-08-14 | 2008-12-10 | 三菱化学株式会社 | 有機金属錯体、発光色素、有機電界発光素子材料、および有機電界発光素子 |
US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
DE10238903A1 (de) | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
CN100439469C (zh) | 2002-08-27 | 2008-12-03 | 富士胶片株式会社 | 有机金属配位化合物、有机el元件及有机el显示器 |
JP2004155728A (ja) † | 2002-11-07 | 2004-06-03 | Mitsubishi Chemicals Corp | 金属錯体の製造方法 |
US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
EP2248870B1 (en) | 2002-11-26 | 2018-12-26 | Konica Minolta Holdings, Inc. | Organic electroluminscent element and display and illuminator |
JP4365199B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4365196B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
CN100387607C (zh) | 2003-03-24 | 2008-05-14 | 南加利福尼亚大学 | Ir的苯基-吡唑配合物 |
US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
EP1717291A3 (de) | 2003-04-15 | 2007-03-21 | Merck Patent GmbH | Mischungen von organischen, zur Emission befähigten Halbleitern und Maxtrixmaterialien, deren Verwendung und diese Mischungen enthaltende Elektronikbauteile |
US7029765B2 (en) | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
WO2004095890A1 (ja) | 2003-04-23 | 2004-11-04 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置、表示装置 |
US20060186791A1 (en) | 2003-05-29 | 2006-08-24 | Osamu Yoshitake | Organic electroluminescent element |
EP3623444B1 (en) | 2003-06-02 | 2021-05-26 | UDC Ireland Limited | Organic electroluminescent devices and metal complex compounds |
TW200504175A (en) | 2003-06-09 | 2005-02-01 | Hitachi Chemical Co Ltd | Metal coordination compound, polymer composition and organic electroluminescence element using the same |
JP2005011610A (ja) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
JP2005042106A (ja) * | 2003-07-08 | 2005-02-17 | Univ Nihon | 芳香族−イリジウム錯体系りん光発光材料の製造方法、芳香族−イリジウム錯体系りん光発光材料、及び芳香族−イリジウム錯体系発光素子 |
ATE522539T1 (de) * | 2003-07-22 | 2011-09-15 | Idemitsu Kosan Co | Iridiumorganischer komplex und elektrolumineszenzgerät, in dem dieser verwendet wird |
US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
TWI390006B (zh) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
US7504049B2 (en) | 2003-08-25 | 2009-03-17 | Semiconductor Energy Laboratory Co., Ltd. | Electrode device for organic device, electronic device having electrode device for organic device, and method of forming electrode device for organic device |
JP4259236B2 (ja) * | 2003-09-05 | 2009-04-30 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子用材料および有機エレクトロルミネッセンス素子 |
HU0302888D0 (en) | 2003-09-09 | 2003-11-28 | Pribenszky Csaba Dr | In creasing of efficacity of stable storage by freezing of embryos in preimplantation stage with pretreatment by pressure |
US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
WO2005042444A2 (ja) | 2003-11-04 | 2005-05-12 | Takasago Perfumery Co Ltd | 白金錯体及び発光素子 |
JP4822687B2 (ja) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
KR100834327B1 (ko) | 2004-03-11 | 2008-06-02 | 미쓰비시 가가꾸 가부시키가이샤 | 전하 수송막용 조성물 및 이온 화합물, 이를 이용한 전하수송막 및 유기 전계 발광 장치, 및 유기 전계 발광 장치의제조 방법 및 전하 수송막의 제조 방법 |
TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
JP4869565B2 (ja) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
US7154114B2 (en) | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
US7601436B2 (en) * | 2004-05-18 | 2009-10-13 | The University Of Southern California | Carbene metal complexes as OLED materials |
US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
US7655323B2 (en) | 2004-05-18 | 2010-02-02 | The University Of Southern California | OLEDs utilizing macrocyclic ligand systems |
US7491823B2 (en) * | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
WO2005123873A1 (ja) | 2004-06-17 | 2005-12-29 | Konica Minolta Holdings, Inc. | 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、表示装置及び照明装置 |
JP5000496B2 (ja) | 2004-06-28 | 2012-08-15 | チバ ホールディング インコーポレーテッド | トリアゾールとベンゾトリアゾールのエレクトロルミネセンス金属錯体 |
US20060008670A1 (en) * | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
US7504657B2 (en) * | 2004-07-23 | 2009-03-17 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display and illuminator |
DE102004057072A1 (de) | 2004-11-25 | 2006-06-01 | Basf Ag | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
CN101087863B (zh) | 2004-12-23 | 2012-06-20 | 西巴特殊化学品控股有限公司 | 具有亲核卡宾配体的电致发光金属络合物 |
US7230107B1 (en) | 2004-12-29 | 2007-06-12 | E. I. Du Pont De Nemours And Company | Metal quinoline complexes |
JP2008526766A (ja) | 2004-12-30 | 2008-07-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機金属錯体 |
US8377571B2 (en) | 2005-02-04 | 2013-02-19 | Konica Minolta Holdings, Inc. | Material for organic electroluminescence element, organic electroluminescence element, display device and lighting device |
KR100803125B1 (ko) | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
WO2006098120A1 (ja) | 2005-03-16 | 2006-09-21 | Konica Minolta Holdings, Inc. | 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 |
DE102005014284A1 (de) | 2005-03-24 | 2006-09-28 | Basf Ag | Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden |
JPWO2006103874A1 (ja) | 2005-03-29 | 2008-09-04 | コニカミノルタホールディングス株式会社 | 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、表示装置及び照明装置 |
GB2439030B (en) | 2005-04-18 | 2011-03-02 | Konica Minolta Holdings Inc | Organic electroluminescent device, display and illuminating device |
US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
JP4533796B2 (ja) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | 有機電界発光素子 |
US8586204B2 (en) | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
WO2006126389A1 (ja) † | 2005-05-25 | 2006-11-30 | Konica Minolta Holdings, Inc. | 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、表示装置及び照明装置 |
EP1888708B1 (en) | 2005-05-31 | 2012-11-21 | Universal Display Corporation | Triphenylene hosts in phosphorescent light emitting diodes |
US8709614B2 (en) | 2005-06-07 | 2014-04-29 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic metal complex and its use in organic electroluminescent device |
WO2007002683A2 (en) | 2005-06-27 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
WO2007004380A1 (ja) | 2005-07-01 | 2007-01-11 | Konica Minolta Holdings, Inc. | 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、表示装置及び照明装置 |
WO2007028417A1 (en) * | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
JP4887731B2 (ja) | 2005-10-26 | 2012-02-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US7462406B2 (en) | 2005-11-15 | 2008-12-09 | Eastman Kodak Company | OLED devices with dinuclear copper compounds |
JPWO2007063796A1 (ja) | 2005-12-01 | 2009-05-07 | 新日鐵化学株式会社 | 有機電界発光素子 |
US7993760B2 (en) | 2005-12-01 | 2011-08-09 | Nippon Steel Chemical Co., Ltd. | Compound for use in organic electroluminescent device and organic electroluminescent device |
KR20160030582A (ko) * | 2006-02-10 | 2016-03-18 | 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 |
US8142909B2 (en) * | 2006-02-10 | 2012-03-27 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
JP4823730B2 (ja) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | 発光層化合物及び有機電界発光素子 |
EP2011790B1 (en) | 2006-04-26 | 2016-06-29 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescence element using the same |
WO2007132678A1 (ja) | 2006-05-11 | 2007-11-22 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子 |
CN101461074B (zh) | 2006-06-02 | 2011-06-15 | 出光兴产株式会社 | 有机电致发光元件用材料及使用了它的有机电致发光元件 |
WO2008009024A2 (en) | 2006-07-14 | 2008-01-17 | Holm, Llc | A portable vacuum system with self-cleaning filter system |
KR20090040896A (ko) | 2006-08-23 | 2009-04-27 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 이들을 이용한 유기 전기발광 소자 |
JP5589251B2 (ja) | 2006-09-21 | 2014-09-17 | 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 |
WO2008044723A1 (fr) | 2006-10-13 | 2008-04-17 | Konica Minolta Holdings, Inc. | Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, dispositif d'affichage et d'éclairage |
US20080102223A1 (en) | 2006-11-01 | 2008-05-01 | Sigurd Wagner | Hybrid layers for use in coatings on electronic devices or other articles |
US7968146B2 (en) | 2006-11-01 | 2011-06-28 | The Trustees Of Princeton University | Hybrid layers for use in coatings on electronic devices or other articles |
EP2080762B1 (en) | 2006-11-09 | 2016-09-14 | Nippon Steel & Sumikin Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
KR101347519B1 (ko) | 2006-11-24 | 2014-01-03 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그것을 이용한 유기 전기발광 소자 |
US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
WO2008072596A1 (ja) | 2006-12-13 | 2008-06-19 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
EP2097938B1 (en) | 2006-12-28 | 2019-07-17 | Universal Display Corporation | Long lifetime phosphorescent organic light emitting device (oled) structures |
WO2008101842A1 (en) | 2007-02-23 | 2008-08-28 | Basf Se | Electroluminescent metal complexes with benzotriazoles |
US8431243B2 (en) | 2007-03-08 | 2013-04-30 | Universal Display Corporation | Phosphorescent materials containing iridium complexes |
CN101687893B (zh) | 2007-04-26 | 2014-01-22 | 巴斯夫欧洲公司 | 含有吩噻嗪s-氧化物或吩噻嗪s,s-二氧化物基团的硅烷及其在oled中的用途 |
EP2170911B1 (en) | 2007-06-22 | 2018-11-28 | UDC Ireland Limited | Light emitting cu(i) complexes |
WO2009003898A1 (de) | 2007-07-05 | 2009-01-08 | Basf Se | Organische leuchtdioden enthaltend carben-übergangsmetall-komplex-emitter und mindestens eine verbindung ausgewählt aus disilylcarbazolen; disilyldibenzofuranen, disilyldibenzothiophenen, disilyldibenzophospholen, disilyldibenzothiophen-s-oxiden und disilyldibenzothiophen-s,s-dioxiden |
WO2009008205A1 (ja) | 2007-07-07 | 2009-01-15 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料 |
US8021574B2 (en) | 2007-07-07 | 2011-09-20 | Idemitsu Kosan Co., Ltd. | Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same |
US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
JP5473600B2 (ja) | 2007-07-07 | 2014-04-16 | 出光興産株式会社 | クリセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US8114530B2 (en) | 2007-07-10 | 2012-02-14 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device utilizing the same |
US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
EP2173811A1 (en) | 2007-07-27 | 2010-04-14 | E. I. du Pont de Nemours and Company | Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles |
KR20160086983A (ko) | 2007-08-08 | 2016-07-20 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
JP2009040728A (ja) | 2007-08-09 | 2009-02-26 | Canon Inc | 有機金属錯体及びこれを用いた有機発光素子 |
KR101642030B1 (ko) | 2007-10-17 | 2016-07-25 | 바스프 에스이 | 가교된 카르벤 리간드를 포함하는 전이 금속 착물 및 이의 용도 |
CN101896493B (zh) * | 2007-10-17 | 2015-04-08 | 巴斯夫欧洲公司 | 具有桥连碳烯配体的过渡金属配合物及其在oled中的用途 |
US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
EP2216313B1 (en) | 2007-11-15 | 2013-02-20 | Idemitsu Kosan Co., Ltd. | Benzochrysene derivative and organic electroluminescent device using the same |
JP5270571B2 (ja) | 2007-11-22 | 2013-08-21 | 出光興産株式会社 | 有機el素子 |
EP2221897A4 (en) | 2007-11-22 | 2012-08-08 | Idemitsu Kosan Co | ORGANIC EL ELEMENT AND ORGANIC EL-MATERIAL SOLUTION |
WO2009073245A1 (en) | 2007-12-06 | 2009-06-11 | Universal Display Corporation | Light-emitting organometallic complexes |
US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
US8471248B2 (en) | 2008-02-12 | 2013-06-25 | Basf Se | Electroluminiscent metal complexes with dibenzo[f,h] quinoxalines |
JP5258339B2 (ja) | 2008-03-24 | 2013-08-07 | 株式会社トクヤマ | シリコン製造プロセス |
CN104141112B (zh) | 2008-05-07 | 2017-09-19 | 普林斯顿大学理事会 | 用于电子器件或其他物品上的涂层中的混合层 |
US8318323B2 (en) | 2008-06-05 | 2012-11-27 | Idemitsu Kosan Co., Ltd. | Polycyclic compounds and organic electroluminescence device employing the same |
US8049411B2 (en) | 2008-06-05 | 2011-11-01 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using 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 |
JP5536054B2 (ja) | 2008-06-30 | 2014-07-02 | ユニバーサル・ディスプレイ・コーポレーション | 硫黄含有基を有するホール輸送材料 |
WO2010027583A1 (en) | 2008-09-03 | 2010-03-11 | Universal Display Corporation | Phosphorescent materials |
TWI555734B (zh) | 2008-09-16 | 2016-11-01 | 環球展覽公司 | 磷光物質 |
WO2010062558A1 (en) | 2008-10-27 | 2010-06-03 | Plextronics Inc. | Charge injection and transport layers |
KR100901888B1 (ko) | 2008-11-13 | 2009-06-09 | (주)그라쎌 | 신규한 전기발광용 유기금속 화합물 및 이를 발광재료로 채용하고 있는 전기발광소자 |
JP5707665B2 (ja) | 2008-12-03 | 2015-04-30 | 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、該素子を備えた照明装置及び表示装置 |
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 |
CN102341403B (zh) | 2009-01-07 | 2014-12-03 | 巴斯夫欧洲公司 | 选自咔唑类、二苯并呋喃类、二苯并噻吩类和二苯并磷杂环戊二烯类的甲硅烷基和杂原子取代的化合物及其在有机电子器件中的应用 |
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 |
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 |
US8586203B2 (en) | 2009-05-20 | 2013-11-19 | Universal Display Corporation | Metal complexes with boron-nitrogen heterocycle containing ligands |
DE102009049587A1 (de) | 2009-10-16 | 2011-04-21 | Merck Patent Gmbh | Metallkomplexe |
CN102741265B (zh) | 2009-10-28 | 2015-12-09 | 巴斯夫欧洲公司 | 杂配卡宾配合物及其在有机电子品中的用途 |
WO2011075644A2 (en) | 2009-12-18 | 2011-06-23 | Plextronics, Inc. | Copolymers of 3,4-dialkoxythiophenes and methods for making and devices |
JP4617393B1 (ja) | 2010-01-15 | 2011-01-26 | 富士フイルム株式会社 | 有機電界発光素子 |
US9156870B2 (en) | 2010-02-25 | 2015-10-13 | Universal Display Corporation | Phosphorescent emitters |
US9193745B2 (en) | 2011-11-15 | 2015-11-24 | Universal Display Corporation | Heteroleptic iridium complex |
-
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- 2007-02-09 KR KR1020167005292A patent/KR20160030582A/ko not_active Application Discontinuation
- 2007-02-09 EP EP10007603.3A patent/EP2243785B1/en active Active
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005049762A1 (en) * | 2003-11-18 | 2005-06-02 | Philips Intellectual Property & Standards Gmbh | Light-emitting device with an iridium complex |
JP2005298483A (ja) * | 2004-03-17 | 2005-10-27 | National Institute Of Advanced Industrial & Technology | イリジウム錯体およびこれを用いた発光材料 |
WO2005113704A2 (en) * | 2004-05-18 | 2005-12-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI637955B (zh) * | 2007-06-20 | 2018-10-11 | 環球展覽公司 | 藍色磷光咪唑并啡啶材料 |
TWI683884B (zh) * | 2007-06-20 | 2020-02-01 | 美商環球展覽公司 | 藍色磷光咪唑并啡啶材料 |
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