TWI627170B - 延遲螢光化合物及使用該延遲螢光化合物之有機電致發光裝置 - Google Patents
延遲螢光化合物及使用該延遲螢光化合物之有機電致發光裝置 Download PDFInfo
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- TWI627170B TWI627170B TW106130389A TW106130389A TWI627170B TW I627170 B TWI627170 B TW I627170B TW 106130389 A TW106130389 A TW 106130389A TW 106130389 A TW106130389 A TW 106130389A TW I627170 B TWI627170 B TW I627170B
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- 230000003111 delayed effect Effects 0.000 title claims abstract description 55
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- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
本發明揭露一種延遲螢光化合物及使用該延遲螢光化合物作為發光層及/或電子傳輸層及/或電洞阻擋層的發光主體的有機電致發光裝置，本發明之有機電致發光裝置具有良好的性能表現。
Description
本發明係為一種化合物及使用該化合物的有機電致發光(Organic Electroluminescence，以下簡稱為有機EL)裝置。具體而言，本發明涉及一種具有通式(1)或通式(2)的延遲螢光化合物，且使用該延遲螢光化合物的有機EL裝置可顯示出極佳的性能。
有機電致發光因其高照度、低重量、超薄外型、無背光的自照明、低能耗、廣視角、高對比度、製造簡單及反應時間快速而應用在平板顯示器中。
有機材料電致發光的首次發現於1950年代早期，由法國南錫大學的安德烈貝諾斯(Andre Bernanose)及其同事所發現。馬丁伯普(Martin Pope)及其紐約大學的同事，於1963年在真空下摻有稠四苯蔥的單一純晶體上，首次觀察到直流(DC)電致發光。
伊士曼柯達(Eastman Kodak)公司的鄧青雲(Ching W.Tang)及史蒂芬范斯萊克(Steven Van Slyke)在1987年公佈了第一個二極體裝置。該裝置採用具有單獨的電洞傳輸層和電子傳輸層的雙層結構，
可導致操作電壓的降低及效率的提高，這促成當今主流的有機EL研究及其裝置生產方式。
一般而言，有機EL裝置由位於兩個電極之間的有機材料層組成，其包括電洞傳輸層(hole transport layer，HTL)、發光層(emitting layer，EML)、電子傳輸層(electron transport layer，ETL)。有機EL的基本機制包括載子的注入、載子傳輸、複合以及形成發光的激子。當外部電壓施加到有機EL裝置時，電子及電洞將分別自陰極及陽極注入，電子將從陰極注入最低未佔用分子軌域(lowest unoccupied molecular orbital，LUMO)中，且電洞將從陽極注入最高佔用分子軌域(highest occupied molecular orbital，HOMO)中。當電子與電洞在發光層中複合時，將會形成激子並隨後發光。當發光分子吸收能量以達到激發態時，根據電子及電洞自旋組合方式，而激子可處於單重態或三重態。透過重組電子及電洞形成75%的激子而達到三重激發態。從三重態的衰減為自旋禁阻，因此，螢光電致發光裝置僅具有25%的內部量子效率。與螢光電致發光裝置相反，磷光有機EL裝置利用自旋軌域交互作用來促進單重態及三重態之間的跨系統交叉，從而獲得單重態和三重態的發射，以及電致發光裝置的內部量子效率從25%到100%。自旋軌域交互作用由一些重原子完成，比如，銥、銠、鉑、鈀，且可從有機金屬複合物的激發金屬配位基電荷轉移(metal-to-ligand charge-transfer transition，MLCT)狀態來觀察磷光躍遷。
近來，安達(Adachi)及同事已開發熱活化型延遲螢光(thermally activated delayed fluorescence，TADF)機制，並將其整合至新型螢光有機EL裝置，其透過在單重態及三重態間使用具有較小能量間隙
的材料得到的逆向系統間穿越(reverse intersystem crossing，RISC)機制，將自旋禁阻的三重態激子轉化為單重態而獲得高效率的激子。然而，於高電流密度中仍需要進一步提高有機EL裝置的發光效率。
有機EL利用三重態激子和單重態激子。磷光有機EL通常在發光層(EML)及電子傳輸層(ETL)之間需要附加電洞阻擋層(hole blocking layer，HBL)，或在發光層(EML)及電洞傳輸層(HTL)之間附加電子阻擋層(electron blocking layer，EBL)，因此，與單重態激子相比，三重態激子壽命更長、擴散長度更長。使用HBL或EBL的目的是限制注入的電洞及電子的複合以及使EML內所產生的激子弛豫，藉此可提高裝置的效率。為了滿足這些作用，電洞阻擋材料或電子阻擋材料必須具有適合於阻斷電洞或電子從EML傳輸至ETL或到HTL的HOMO和LUMO能階。
對於主動矩陣有機發光二極體(active-matrix organic light-emitting diode，AMOLED)或有機發光二極體(organic light-emitting diode，OLED)為發光面板的全彩平板顯示器來說，使用於發光層中磷光主體材料之，對於工業實務使用而言，半衰期、效率及驅動電壓方面仍無法令人滿意。除此之外，為了呈現有機EL裝置的優異性能，磷光發光主體材料需與其他有機薄膜層(例如：電洞阻擋層及電子傳輸層)配位，以達到低能耗、長半衰期及高效率。因此，需要設計及開發用於有機EL裝置的新型材料。
在本發明中，為了使有機EL裝置中延遲螢光化合物的偶極材料延遲半衰期、提高效率及顯示極佳性能，我們使用一系列的苯并
[c][1,2,5]噻二唑(benzo[c][1,2,5]thiadiazole)、苯並[c][1,2,5]二唑(benzo[c][1,2,5]oxadiazole)、苯并[c][1,2,5]硒二唑(benzo[c][1,2,5]selenadiazole)、萘并[2,3-c][1,2,5]噻二唑(naphtho[2,3-c][1,2,5]thiadiazole)、萘并[2,3-c][1,2,5]二唑(naphtho[2,3-c][1,2,5]oxadiazole)及萘并[2,3-c][1,2,5]硒二唑(naphtho[2,3-c][1,2,5]selenadiazole)骨架作為供體並與二氫吲哚咔唑基團(dihydroindolocarbazole group)、二氫茚并咔唑基團(dihydroindenocarbazole group)、啡噻嗪基團(phenothiazine group)、啡嗪基團(phenoxazine group)、二氫吖啶基團(dihydroacridine group)、二氫啡嗪基團(dihydrophenazine group)的供體特徵聯接，二氫啡嗪基團作為偶極材料，以完成如通式(1)或通式(2)的延遲螢光化合物。先前技術：合成金屬161(2011)718-723基於具有咔唑(carbazole)部份的2,1,3-苯并噻二唑(2,1,3-benzothiadiazole)揭露了有效的發光材料，WO2015/105137A1亦揭露了具有咔唑衍生物作為延遲螢光化合物的苯并噻二唑偶聯(benzothiadiazole coupling)。但本文未有先前技術展示了本發明的用於有機EL裝置的延遲螢光化合物。
根據上述原因，本發明之目的為解決現有技術的這些問題，並提供一種發光裝置，其在熱穩定性、高發光效率及長衰期上表現極佳。本發明揭露一種具有通式(1)或通式(2)的有機化合物，其用作發光層的延遲螢光材料及/或發光層及/或電子傳輸層及/或電洞阻擋層的磷光
發光主體，該等層具有良好的電荷載子遷移率，且極佳的使用壽命可降低有機EL裝置的驅動電壓和能耗、增加有機EL裝置的效率並延長其半衰期。
本發明具有工業應用的經濟優點。相應地，本發明揭露了可用於有機EL裝置的延遲螢光化合物。所述延遲螢光化合物由下式(1)或式(2)表示：
6‧‧‧透明電極
7‧‧‧電洞注入層
8‧‧‧電洞傳輸層
9‧‧‧電子阻擋層
10‧‧‧發光層
11‧‧‧電洞阻擋層
12‧‧‧電子傳輸層
13‧‧‧電子注入層
14‧‧‧金屬電極
圖1為本發明之用於有機電致發光裝置之延遲螢光化合物之實施例的有機EL裝置之示意圖
圖2為化合物8的延遲螢光特性的瞬時衰變固化。圖3為化合物8的UV-Vis(nm)及PL(nm)圖表。
本發明研究用於使用化合物的有機EL裝置的延遲螢光化合物。下面將詳細說明生產、結構及組成部份，以使對本發明的理解更充分。本發明的應用明顯不受限於所屬技術領域具有通常知識者熟知的具
體細節。另一方面，眾所周知的一般組成成份和程序不作詳細說明，以避免對本發明造成不必要的限制。現在將在下面更詳細地介紹本發明的一些優選實施例。然而，應該瞭解本發明可實際操作於各種其他實施例中，而非本發明詳細所述的實施例中，也就是說，本發明還可廣泛地應用於其他實施例，且本發明的範圍沒有明確的限制，除隨附申請專利權利範圍限定的內容。
在本發明的第一個實施例中，揭露了可用作有機EL裝置的發光層的熱活化延遲螢光(thermally activated delayed fluorescence，TADF)材料。所述延遲螢光化合物由下式(1)或式(2)表示：
如上述延遲螢光化合物式(1)或式(2)，其中L1及L2由下式(6)表示：
其中Z1及Z5分別表示氮原子或C(Rs)，且各個Rs表示氫原子、苯基、具有1到30個碳原子的取代或未取代烷基及具有6到30個碳原子的取代或未取
代芳基。
在本實施例中，該延遲螢光化合物的單重態能量與該延遲螢光化合物的三重態能量之間的差異小於0.25eV。在本實施例中，一些延遲螢光化合物所示如下：
本發明中延遲螢光化合物的詳細製備由示例性實施例闡明，但本發明不限於示例性實施例。實施例1至實施例4展示出了本發明中延遲螢光化合物的製備範例。實施例5展示出有機EL裝置及I-V-B的製作、有機EL裝置測試報告的半衰期。
實施例1
化合物4的合成
4,7-雙(12,12-二甲基茚并[2,1-a]咔唑-11(12氫)-基)苯并[c][1,2,5]噻二唑(4,7-bis(12,12-dimethylindeno[2,1-a]carbazol-11(12H)-yl)benzo[c][1,2,5]thiadiazole)的合成
在氮氣中將5g(17.0mmol)4,7-二溴苯并[c][1,2,5]噻二唑(4,7-dibromobenzo[c][1,2,5]thiadiazole)、12.5g(44.2mmol)12,12-二甲基-11,12-二氫茚並[2,1-a]咔唑(12,12-dimethyl-11,12-dihydroindeno[2,1-a]carbazole)、0.3g(0.16mmol)CuI、0.1g(0.51mmol)18-冠-6(18-Crown-6)、9.5g(68.4mmol)K2CO3及25ml NMP混合物迴流過夜。反應完成後，使混合物冷卻至室溫。將溶液倒入水中，隨後過濾。固體使用DMF再結晶並透過昇華純化，得到3.6g產物(產率31%)。MS(m/z,FAB+)：699.5
實施例2
化合物8的合成
4,7-雙(12,12-二甲基茚并[2,1-a]咔唑-11(12氫)-基)苯并[c][1,2,5]噻二唑(4,7-bis(12,12-dimethylindeno[2,1-a]carbazol-11(12H)-yl)benzo[c][1,2,5]thiadiazole)的合成
在氮氣中將5g(14.5mmol)4,7-二溴苯并[c][1,2,5]噻二唑(4,7-dibromobenzo[c][1,2,5]thiadiazole)、10.7g(37.8mmol)12,12-二甲基-11,12-二氫茚并[2,1-a]咔唑(12,12-dimethyl-11,12-dihydroindeno[2,1-a]carbazole)、0.3g(0.15mmol)CuI、0.1g(0.44mmol)18-冠-6(18-Crown-6)、8.0g(58.0mmol)K2CO3及25ml NMP混合物迴流過夜。反應完成後，使混合物冷卻至室溫。將溶液倒入水中，隨後過濾。固體使用DMF重結晶並透過昇華純化，得到2.9g產物(產率28%)。MS(m/z,FAB+)：748.9
實施例3
化合物29的合成
4,7-二(10氫-啡噻嗪-10-基)苯并[c][1,2,5]噻二唑(4,7-di(10H-phenothiazin-10-yl)benzo[c][1,2,5]thiadiazole)的合成
將2g(6.8mmol)4,7-二溴苯并[c][1,2,5]噻二唑
(4,7-dibromobenzo[c][1,2,5]thiadiazole)、3.4g(17mmol)啡噻嗪(phenothiazine)、1.3g(6.8mmol)碘化銅(I)(Copper(I)iodide)、4.4g(13.6mmol)Cs2CO3、1.25g(4.76mmol)18-冠-6(18-Crown-6)及40ml鄰二氯苯(o-Dichlorobenzene)混合物除氣並放置在氮氣中，隨後在180℃加熱16h。在反應完成後，將混合物熱過濾。液體使用二氯甲烷及水萃取，使用無水硫酸鎂乾燥，移除溶劑並透過矽膠管柱層析法純化，得到2.5g黃橙色固體產物(產率70%)。
實施例4
化合物31的合成
4,7-雙(9,9-二甲基吖啶-10(9氫)-基)苯并[c][1,2,5]噻二唑(4,7-bis(9,9-dimethylacridin-10(9H)-yl)benzo[c][1,2,5]thiadiazole)的合成
將2g(6.8mmol)4,7-二溴苯并[c][1,2,5]噻二唑(4,7-dibromobenzo[c][1,2,5]thiadiazole)、3.6g(17mmol)9,9-二甲基-9,10-二氫吖啶(9,9-dimethyl-9,10-dihydroacridine)、1.3g(6.8mmol)碘化銅(I)(Copper(I)iodide)、4.4g(13.6mmol)Cs2CO3、1.25g(4.76mmol)18-冠-6(18-Crown-6)及40ml鄰二氯苯(o-Dichlorobenzene)混合物除氣並放置在氮氣中，隨後在180℃加熱16h。在反應完成後，將混合物熱過濾。液體使用二氯甲烷及水萃取，使用無水硫酸鎂乾燥，移除溶劑並透過矽膠
管柱層析法純化，得到2.2g橙色固體產物(產率58%)。
延遲螢光化合物之光物理特性的測量方法
光物理特徵：合成的化合物在高真空下透過溫度梯度昇華進行純化，隨後在之後的研究中使用。透過在基礎壓力<10-6torr的真空室中以1-2A/sec的速率於石英基材上熱蒸發來製備光物理特徵的薄膜。所得薄膜及吸收溶液的吸收光譜由UV-vis-NIR分光光度儀(UV-1650 PC，Shimadzu)檢測。光激螢光(Photoluminescence，PL)光譜、冷光量子吸收量(photoluminescence quantum yields，PLQYs)及磷光光譜由螢光分光光度儀(FluoroMax-P，Horiba Jobin Yvon Inc.)檢測薄膜或稀釋溶液的PLQYs使用配備校準積分球的該螢光分光光度儀來檢測。使用選定的單色激發光來激發位於校準積分球中的激發樣本。透過對比單色激發光及PL發射的光譜強度，測定PL量子吸收量。透過配有微秒閃光燈作為脉衝激發光源的螢光分光光度儀在77K(液氮溫度)下進行薄膜或稀釋溶液的磷光光譜。在發射光譜的脉衝激發及收集之間***10-ms延遲時間。透過使用具有螢光壽命系統的時間相關單光子計數技術(FluoroCube,Horiba Jobin Yvon Inc.)及來自UV發光二極管的奈秒(nanosecond)脉衝光激發(300nm)來監控PL峰值處強度的衰減，以確定時間解析(time-resolved)PL(PL衰減曲綫)。將樣本放置在具有溫度控制的真空低溫恆溫室中。使用具有發射光譜的脉衝激發及收集之間為200-ns延遲時間及10-ns延遲時間的相同螢光壽命系統來收集瞬時成份及延遲成份的PL光譜。電化學特徵：使用CHI619B恆電位儀的循環伏安法來量測氧化/還原電位。透過使用0.1M n-Bu4NPF6(TBAPF6)在CH2Cl2中作為支持電解質，掃描速率
為100mV s-1，藉由循環伏安法測定氧化電位。透過使用0.1M n-Bu4NClO4(TBAP)在DMF中作為支持電解質，掃描速率為100mV s-1，記錄還原電位。使用包含銀/氯化銀(Ag/AgCl)、鉑金線及玻璃碳電極分別作為參考、計數及工作電極的標準3-電極電池。記錄所有電位以Ag/AgCl(飽和)作為參考電極時，CH2Cl2/TBAPF6中二茂鐵鐵/二茂鐵離子(Fc/Fc+)氧化還原發生於氧化出現在E’o=+0.47V，且二茂鐵/二茂鐵離子(Fc/Fc+)氧化還原發生於還原出現在E”o=+0.51V。
圖2顯示化合物8的延遲螢光特徵的甲苯溶液的瞬時衰變曲綫的測量，且圖3顯示出了化合物8的光致發光光譜的測量。
生產有機EL裝置的一般方法
提供阻值為9~12歐姆/平方(ohm/square)及厚度為120~160nm的銦錫氧化物(Indium Tin Oxide，ITO)塗層玻璃並在超聲波浴(例如，洗滌劑、等離子水)中進行多步驟清洗。在氣相沉積有機層之前，透過紫外光(UV)和臭氧進一步處理清洗後的ITO基底。ITO基底的所有預處理過程在潔淨室(100級)內進行。
這些有幾次透過高真空單位(10-7Torr)的氣相沉積依次施加在ITO基底上，比如：電阻加熱石英船。每層的厚度和氣相沉積速率(0.1~0.3nm/sec)由石英晶體監視器來精確監控或設置。如上所述，還可能使單個層包含多於一種化合物，即一般主體材料摻雜有摻雜材料。這透過來自兩個或多個來源的共氣相來實現。
在該有機EL裝置中，使用二吡嗪[2,3-f：2,3-]喹喔啉-2,3,6,7,10,11-六腈(dipyrazino[2,3-f：2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitr
ile)(HAT-CN)用作電洞注入層，且N4,N4’-二二(聯苯-4-基)-N4,N4’-二二苯基聯苯基-4,4’-二胺(N4,N4’-di(biphenyl-4-yl)-N4,N4’-diphenylbiphenyl-4,4’-diamine)(HT1)用作電洞傳輸層，N-(聯苯-4-基)-9,9-二甲基-N-(4’-苯基聯苯-4-基)-9H-茀-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4’-phenyl biphenyl-4-yl)-9H-fluoren-2-amine)(EB2)用作電洞阻擋層，H1用作與本發明相當或標準的磷光主體及延遲螢光主體。所示化學結構如下：
本發明中製備的以下延遲螢光範例可透過有機EL裝置驗證為並用作為延遲螢光摻雜劑、磷光主體、電洞阻擋材料或電子傳輸材料。使用對比化合物Q(CCQ)作為本發明中對比化合物的延遲螢光摻雜劑。
有機銥絡合物廣泛用作發光層的磷光摻雜劑，Ir(ppy)3廣泛用作有機EL裝置的發光層的磷光綠色摻雜劑。
2,2’,2”-(1,3,5-苯并三嗪)-三(1-苯基-1-H-苯并咪唑)(2,2’,2”-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole))(TPBi)及HB3(參見下列化學結構)用作電洞阻擋材料(HBM)，且2-(10,10-二甲基-10氫-茚并[2,1-b]三亞苯-12-基)-4,6-二苯基-1,3,5-三嗪(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,6-diphenyl-1,3,5-triazine)(ET2)用作電子傳輸材料，以在有機EL裝置中與8-羥基喹啉-鋰(8-hydroxyquinolato-lithium，LiQ)共沉積。本發明中用於生產標準有機EL裝置控制及可比材料的其他OLED材料的先前技術所示如下：
有機EL裝置一般包含透過熱蒸發作為陰極的低功函數金屬，比如，Al、Mg、Ca、Li及K，且該低功函數金屬可有助於電子從陰極注入電子傳輸層。另外，在陰極及電子傳輸層之間引入薄膜電子注入
層，用於減少電子注入障礙並提高有機EL裝置性能。習知的電洞注入層材料為具有低功函數的金屬鹵化物或金屬氧化物，比如：LiF、LiQ、MgO或Li2O。另一方面，在製作有機EL裝置之後，透過使用PR650光譜掃描光譜儀量測EL光譜及CIE座標。此外，電流/電壓、發光/電壓及產率/電壓特徵都使用吉時利(Keithley)2400可編程電壓電流源來檢測。上述設備在室溫(約25℃)及大氣壓下操作。
實施例5
使用與上述一般方法類似的程序，生產具有下列裝置結構的有機EL裝置(參閱圖1)。有機EL裝置包含，透明電極6~金屬電極14，其之間依序分別為沉積在透明電極6上的電洞注入層7，沉積在電洞注入層7上的電洞傳輸層8，沉積在電洞傳輸層8上的電子阻擋層9，沉積在電子阻擋層9上的發光層10，沉積在發光層10上的電洞阻擋層11，沉積在電洞阻擋層11上的電子傳輸層12，沉積在電子傳輸層12上的電子注入層13，以及沉積在電子注入層13上的金屬電極14。裝置：ITO/HAT-CN(20nm)/HT1(110nm)/EB2(5nm)/主體+10%~30%dopant(30nm)/HBM(10nm)/ETM doped 40% LiQ(35nm)/LiQ(1nm)/Al(160nm)有機EL裝置的I-V-B(1000nits亮度時)的測試報告如表1所示。
在上述有機EL裝置測試報告的最佳實施例中(參閱表1)，我們揭露了本發明中具有通式(1)或通式(2)的延遲螢光化合物作為發光層及/或電子傳輸層及/或電洞阻擋層的發光主體及/或有機EL器件裝置的發光層的延遲螢光(TADF)材料時，本發明之有機EL裝置的性能顯現比有機EL材料的先前技術更好。尤其是，本發明中使用二氫吲哚咔唑骨架(比如C4及C8)用作有機EL裝置的延遲螢光化合物時，顯現出了比先前技術中使用咔唑核(比如CCQ)更好的效率。
總而言之，本發明揭示了一種延遲螢光化合物，其可作為發光層及/或電子傳輸層及/或電洞阻擋層的磷光發光主體及/或作為有機EL裝置的發光層的延遲螢光材料。所述延遲螢光化合物由下式(1)或式(2)表示：
鑒於上述教示，可能作出多數明顯的修改及變化。因此，應該瞭解，在隨附權利要求的範圍內，本發明可以除本文具體所述方
式之外的其他方式來進行實踐。雖然，本文已示出並說明了具體實施例，但對於所屬領域具有通常知識者來說，可在不偏離旨在單獨由隨附權利要求所限制的那些的情況下，作出多數修改。
Claims (18)
- 一種延遲螢光化合物，其由下式(1)或式(2)表示：
其中D1及D2中的至少一個分別選自由式(3)至式(4)組成的群組：
L1及L2表示單鍵、具有6到30個環碳原子的取代或未取代亞芳基或具有3到30個環碳原子的取代或未取代雜亞芳基，X分別選自氧原子、硫原子及硒原子，p表示0到4的整數，Z為包含選自O、S、NR9及Si(R10)(R11)組成的原子或基團的二價橋，Y1至Y6表示氮原子或C(Rs)，且各個Rs表示氫原子、具有1到30個碳原子的取代或未取代烷基、或具有6到30個碳原子的取代或未取代芳基；R1至R4及R9至R11分別選自由氫原子、鹵化物、具有1到30個碳原子的取代或未取代烷基、具有6到30個碳原子的取代或未取代芳基、具有6到30個碳原子的取代或未取代芳烷基及具有3到30個碳原子的一取代或未取代雜芳基組成的群組。
- 如申請專利範圍第1項所述之延遲螢光化合物，其中L1及L2由下式(6)表示：其中Z1至Z5分別表示氮原子或C(Rs)，且各個Rs表示氫原子、具有1到30個碳原子的取代或未取代烷基、或具有6到30個碳原子的取代或未取代芳基。
- 如申請專利範圍第1項所述之延遲螢光化合物，其中該延遲螢光化合物的單重態能量與該延遲螢光化合物的三重態能量之間的差異小於0.25eV。
- 如申請專利範圍第1項所述之延遲螢光化合物，具有式(1)或式(2)結構的該化合物為一發光材料。
- 如申請專利範圍第4項所述之延遲螢光化合物，其中該發光材料發出延遲螢光。
- 一種有機電致發光裝置，其包含由陰極及陽極組成的一對電極對，且其中該對電極對之間至少包含一層發光層、一層或多層有機薄膜層，其中該發光層、該有機薄膜層其中之一或二者包含具有一如申請專利範圍第1項所述之通式(1)或通式(2)的該延遲螢光化合物。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中該延遲螢光化合物的單重態能量與該延遲螢光化合物的三重態能量之間的差異小於0.25eV。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中該發光層包括該延遲螢光化合物及/或該螢光化合物。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有通式(1)或通式(2)之該延遲螢光化合物的該發光層為一延遲螢光主體材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有通式(1)或通式(2)之該延遲螢光化合物的該發光層為一延遲螢光摻雜材料。
- 如申請專利範圍第10項所述之有機電致發光裝置，其中該發光層包括一第二螢光摻雜材料。
- 如申請專利範圍第9項所述之有機電致發光裝置，其中該發光層包括一第二螢光主體材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有通式(1)或通式(2)之該延遲螢光化合物的該發光層為一磷光主體材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有通式(1)或通式(2)之該延遲螢光化合物的該有機薄膜層為一電洞阻擋材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有通式(1)或通式(2)之該延遲螢光化合物的該有機薄膜層為一電子傳輸層(ETL)材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中該裝置為一有機發光裝置。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中該裝置為一發光面板。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中該裝置為一背光面板。
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| US15/390,720 US10224488B2 (en) | 2016-12-27 | 2016-12-27 | Delayed fluorescence compound for organic EL device and using the same |
| US15/390,720 | 2016-12-27 |
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| TWI627170B true TWI627170B (zh) | 2018-06-21 |
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| TW106130389A TWI627170B (zh) | 2016-12-27 | 2017-09-06 | 延遲螢光化合物及使用該延遲螢光化合物之有機電致發光裝置 |
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| CN (1) | CN107674087A (zh) |
| TW (2) | TWI633102B (zh) |
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| KR20180062561A (ko) * | 2016-11-30 | 2018-06-11 | 삼성디스플레이 주식회사 | 다환 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| CN110386930B (zh) * | 2018-04-18 | 2023-07-14 | 香港科技大学 | 聚集诱导发光化合物、其制备方法及其应用 |
| CN109369684B (zh) * | 2018-11-01 | 2021-07-27 | 华东师范大学 | 一类电子供体-受体-供体荧光分子及制备方法和应用 |
| CN109659442B (zh) * | 2018-12-13 | 2022-04-26 | 云谷（固安）科技有限公司 | 一种有机电致发光器件和显示装置 |
| US20200207752A1 (en) * | 2018-12-26 | 2020-07-02 | Int Tech Co., Ltd. | Organic electroluminescent compound and organic electroluminescent device containing the same |
| CN109796451B (zh) * | 2019-02-18 | 2020-07-14 | 中国科学院化学研究所 | 一种以萘啶作为电子受体的多色热激活延迟荧光材料及其制备方法与应用 |
| CN115279748A (zh) * | 2020-02-04 | 2022-11-01 | 九州有机光材股份有限公司 | 化合物、发光材料、延迟荧光材料及有机光器件 |
| CN112341452A (zh) * | 2020-11-06 | 2021-02-09 | 广东工业大学 | 一种化合物及其制备方法和三重态-三重态湮灭上转换体系 |
| GB2609688A (en) * | 2021-08-06 | 2023-02-15 | Sumitomo Chemical Co | Compound |
| CN116709880B (zh) * | 2023-08-10 | 2023-09-29 | 南开大学 | 基于单磷光分子场效应管的单光子源及其制备方法 |
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| CN103187531A (zh) * | 2011-12-30 | 2013-07-03 | 昆山维信诺显示技术有限公司 | 有机电致发光器件及双极性有机化合物的用途 |
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| AU2003221969A1 (en) * | 2002-04-19 | 2003-11-03 | 3M Innovative Properties Company | Materials for organic electronic devices |
| JP6383538B2 (ja) * | 2014-01-08 | 2018-08-29 | 株式会社Ｋｙｕｌｕｘ | 発光材料、有機発光素子および化合物 |
| EP3020783B1 (en) * | 2014-11-12 | 2018-06-06 | LG Display Co., Ltd. | Delayed fluorescence compound, and organic light emitting diode and display device using the same |
| KR102454041B1 (ko) * | 2014-12-05 | 2022-10-14 | 엘지디스플레이 주식회사 | 지연 형광 화합물, 이를 포함하는 유기발광다이오드소자 및 표시장치 |
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| CN103187531A (zh) * | 2011-12-30 | 2013-07-03 | 昆山维信诺显示技术有限公司 | 有机电致发光器件及双极性有机化合物的用途 |
Also Published As
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| TW201823240A (zh) | 2018-07-01 |
| US10224488B2 (en) | 2019-03-05 |
| TWI633102B (zh) | 2018-08-21 |
| CN107674087A (zh) | 2018-02-09 |
| TW201823241A (zh) | 2018-07-01 |
| US20180182975A1 (en) | 2018-06-28 |
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