TWI554506B - 在磷光發光二極體中的含二苯并噻吩物質 - Google Patents

在磷光發光二極體中的含二苯并噻吩物質 Download PDF

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TWI554506B
TWI554506B TW103106912A TW103106912A TWI554506B TW I554506 B TWI554506 B TW I554506B TW 103106912 A TW103106912 A TW 103106912A TW 103106912 A TW103106912 A TW 103106912A TW I554506 B TWI554506 B TW I554506B
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林世崇
艾雷西 波里索維奇 迪亞金
傑納柏 艾榭納維
渥特Ｈ 亞吉爾
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環球展覽公司
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Description

在磷光發光二極體中的含二苯并噻吩物質
本發明係關於有機發光裝置(OLED)。更詳言之，本發明係關於磷光發光物質及可具有改良之裝置壽命之裝置。
本申請案主張於2007年12月28日申請之美國臨時申請案第61/017,480號之優先權，其揭示內容全文以引用的方式明確地併入本文中。本申請案亦係關於2007年12月28日申請之國際申請案第PCT/US07/89131號。
所主張之發明係由聯合大學公司研究協議之以下締約方中的一或多者進行，以其名義進行及/或聯合其進行：Regents of the University of Michigan、Princeton University、The University of Southern California及the Universal Display Corporation。該協定在所主張之發明進行之日及之前有效且所主張之發明係由於在該協定範疇內所進行之活動而進行。
利用有機物質之光電裝置由於許多原因而日益需要。用以製造該等裝置之許多物質相對廉價，因此有機光電裝置具有優於無機裝置之成本優勢潛力。此外，有機物質之固有特性(諸如其可撓性)可使其十分適用於諸如在可撓性基板上製造的特定應用。有機光電裝置之實例包括有機發光裝置(OLED)、有機光電晶體、有機光電電池及有機 光偵測器。對OLED而言，有機物質可具有優於習知物質之效能優勢。舉例而言，有機發射層發光之波長一般易於用適當摻雜物調節。
OLED利用有機薄膜，當跨越裝置施加電壓時該薄膜發光。OLED正成為用於諸如平板顯示器、照明及背光之應用的日益受關注之技術。若干OLED物質及組態係描述於美國專利第5,844,363號、第6,303,238號及第5,707,745號中，該等專利之全文係以引用的方式併入本文中。
磷光發射分子之一種應用為全色顯示器。該顯示器之工業標準要求經調適以發射特定色彩(稱為"飽和"色彩)之像素。詳言之，此等標準要求飽和紅色、綠色及藍色像素。可使用此項技術中熟知之CIE座標來量測色彩。
綠色發射分子之一實例為具有式I結構，表示為Ir(ppy)3之參(2-苯基吡啶)銥：
其中及在本文中隨後的圖中，吾人以直線形式描述自氮至金屬(此處Ir)之配價鍵。
本文中所使用之術語"有機"包括可用以製造有機光電裝置之聚合物質以及小分子有機物質。"小分子"係指不為聚合物之任何有機物質，且"小分子"事實上可相當大。在一些情況下，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自"小分子"類別中移除分子。小分子亦可(例如)作為在聚合物主鏈上之側接基團或作為主鏈之一部分併入聚合物中。小分子亦可用作樹狀體之核心部分，該樹狀體係由一系列建立在核心部分上之化學殼(chemical shell)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 "，且咸信目前用於OLED領域中之所有樹狀體均為小分子。
本文中所使用之"頂部"意謂距基板最遠，而"底部"意謂距基板最近。在將第一層描述為"經安置於"第二層上時，第一層係更遠離基板安置。除非規定第一層與第二層"接觸"，否則在第一層與第二層之間可存在其他層。舉例而言，可將陰極描述為"經安置於"陽極之上，即使在其間存在各種有機層。
本文中所使用之"溶液可處理"意謂能夠呈溶液或懸浮液形式溶解、分散於液體介質中或於液體介質中輸送及/或自液體介質沈積。
當咸信配位體直接促進發射性物質之光活性特性時，配位體可稱為"光活性的"。當咸信配位體不促進發射性物質之光活性特性時，將配位體稱為"輔助的"，儘管輔助配位體可改變光活性配位體之特性。
如本文中所使用且如熟習此項技術者所一般理解，若第一能階更接近於真空能階，則第一"最高佔據分子軌道"(HOMO)或"最低未占分子軌道"(LUMO)能階"大於"或"高於"第二HOMO或LUMO能階。因為電離電位(IP)經量測為相對於真空能階之負能量，所以較高HOMO能階對應於具有較小絕對值之IP(負性較小之IP)。類似地，較高LUMO能階對應於具有較小絕對值之電子親和力(EA)(負性較小之EA)。在頂部為真空能階之習知能階圖表上，物質之LUMO能階比相同物質之HOMO能階高。"較高"HOMO或LUMO能階似乎比"較低"HOMO或LUMO能階更接近於該圖表之頂部。
如本文中所使用且如熟習此項技術者一般理解，若第一功函數具有較高絕對值，則第一功函數"大於"或"高於"第二功函數。由於功函數一般經量測為相對於真空能階之負數，故其意謂"較高"功函數負值更高。在頂部為真空能階之習知能階圖表上，"較高"功函數被說明為在向下方向上較遠離真空能階。因此，HOMO及LUMO能階之定義 遵循與功函數不同之慣例。
關於OLED及上述定義之更詳細描述可見於全文以引用的方式併入本文中之美國專利第7,279,704號。
提供一種新型物質。該新型物質具有選自由下列各物組成之群之含二苯并噻吩的化合物：
其中R1至R6各自獨立選自由任何芳基及烷基取代基及H組成之群，且其中R1至R6各自可表示多個取代。在一態樣中R1至R6均為H。
亦提供一種有機發光裝置。該裝置具有陽極、陰極及安置於陽極與陰極之間之有機層。有機層另外包含含有化合物之物質，該化合物來自由具有或不具有取代基之如上所述化合物1G至12G組成之群。有機層較佳為具有主體及發射摻雜物之發射層，且該化合物為主體。化合物亦可較佳用作強化層中之物質。
提供新穎物質。該等物質具有選自由下列各物組成之群之含二 苯并噻吩及/或含二苯并呋喃的化合物：
其中R1至R8各自獨立選自由任何芳基及烷基取代基及H組成之群，且其中R1至R8各自可表示多個取代。在一態樣中，R1至R8均為H。
亦提供一種有機發光裝置。該裝置具有陽極、陰極及安置於陽極與陰極之間之有機層。有機層另外包含含有化合物之物質，該化合物來自由具有或不具有取代基之如上所述化合物2G至35G組成之群。有機層較佳為具有主體及發射摻雜物之發射層，且該化合物為主體。化合物亦可較佳用作強化層中之物質。
亦提供一種消費型產品。該產品含有具有陽極、陰極及安置於陽極與陰極之間之有機層的裝置，其中該有機層另外包含含有化合物之物質，該化合物來自由具有或不具有取代基之如上所述化合物2G至35G組成之群。
100‧‧‧有機發光裝置
110‧‧‧基板
115‧‧‧陽極
120‧‧‧電洞注入層
125‧‧‧電洞傳輸層
130‧‧‧電子阻擋層
135‧‧‧發射層
140‧‧‧電洞阻擋層
145‧‧‧電子傳輸層
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‧‧‧倒轉OLED
210‧‧‧基板
215‧‧‧陰極
220‧‧‧發射層
225‧‧‧電洞傳輸層
230‧‧‧陽極
圖1展示有機發光裝置。
圖2展示不具有獨立電子傳輸層之倒轉的有機發光裝置。
圖3展示包括本文中所揭示之化合物之有機發光裝置。
圖4展示圖3之裝置的正規化發光對時間之曲線圖。
圖5展示圖3之裝置的外量子效率對亮度之曲線圖。
圖6展示圖3之裝置的功率功效對亮度之曲線圖。
圖7展示圖3之裝置的亮度對電壓之曲線圖。
圖8展示圖3之裝置的EL強度對波長之曲線圖。
圖9展示包括本文中所揭示之化合物之有機發光裝置。
圖10展示圖9之裝置的外量子效率對亮度之曲線圖。
圖11展示圖9之裝置的功率功效對亮度之曲線圖。
圖12展示圖9之裝置的亮度對電壓之曲線圖。
圖13展示圖9之裝置的EL強度對波長之曲線圖。
圖14展示含二苯并噻吩之化合物。
一般而言，OLED包含至少一個安置於陽極與陰極之間且與陽極及陰極電連接之有機層。當施加電流時，陽極注入電洞且陰極注入電子至有機層中。所注入之電洞及電子各自朝帶相反電荷之電極遷移。當電子及電洞定位於相同分子上時，形成"激子"，其為具有激發能態之局部電子-電洞對。當激子經由光電發射機制鬆馳時發光。在一些情況下，激子可定位於受激準分子或激發複合物上。亦可發生諸如熱 鬆弛之非輻射機制，但一般視其為不需要的。
如(例如)全文以引用的方式併入之美國專利第4,769,292號中所揭示，初始OLED使用自其單一態發射光("螢光")之發射分子。螢光發射一般在小於10奈秒之時段內發生。
近期，已表明具有自三重態發光("磷光")之發射物質之OLED。全文以引用的方式併入之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3,4-6號(1999)("Baldo-II")。磷光係更詳細描述於以引用的方式併入之美國專利第7,279,704號第5-6欄。
圖1展示有機發光裝置100。該等圖不一定按比例繪製。裝置100可包括基板110、陽極115、電洞注入層120(HIL)、電洞傳輸層125(HTL)、電子阻擋層130、發射層135、電洞阻擋層140、電子傳輸層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之化合物陰極。可藉由順次沈積所述層製造裝置100。此等各層以及實例物質之特性及功能係更詳細描述於以引用的方式併入之US 7,279,704第6-10欄。
可利用此等層之每一者許多實例。舉例而言，可撓性及透明基板-陽極組合係揭示於全文以引用的方式併入之美國專利第5,844,363號中。p摻雜電洞傳輸層之實例為如全文以引用的方式併入之美國專利申請公開案第2003/0230980號所揭示以50：1之莫耳比摻雜有F.sub.4-TCNQ之m-MTDATA。發射性物質及主體物質之實例係揭示於Thompson等人之美國專利第6,303,238號中，其全文係以引用的方式併入。n摻雜電子傳輸層之實例為如全文以引用的方式併入之美國專 利申請公開案第2003/0230980號所揭示的以1：1莫耳比摻雜有Li之BPhen。全文以引用的方式併入之美國專利第5,703,436號及第5,707,745號揭示包括具有諸如Mg：Ag之金屬薄層的化合物陰性之陰極之實例，該金屬薄層具有上覆透明、導電之濺鍍沈積ITO層。全文以引用的方式併入之美國專利第6,097,147號及美國專利申請公開案第2003/0230980號更詳細地描述阻擋層之理論及用途。注入層之實例係提供於全文以引用的方式併入之美國專利申請公開案第2004/0174116號中。保護層之描述可見於全文以引用的方式併入之美國專利申請公開案第2004/0174116號中。"強化層"在裝置中佔據與上述阻擋層相同之位置且可具有阻擋功能性或改良裝置效能之其他功能性。
圖2展示倒轉OLED 200。該裝置包括基板210、陰極215、發射層220、電洞傳輸層225及陽極230。裝置200可藉由順次沈積所述層而製造。因為大多數常見OLED組態具有安置於陽極上之陰極，且裝置200具有安置於陽極230下之陰極215，所以裝置200可稱為"倒轉"OLED。類似於彼等關於裝置100描述者之物質可用於裝置200之相應層。圖2提供如何可將某些層自裝置100之結構省去的一實例。
藉由非限制性實例，提供圖1及2中說明之簡單層狀結構，且應瞭解本發明之實施例可與多種其他結構聯合使用。所描述之特定物質及結構本質上為例示性的，且可使用其他物質及結構。功能性OLED可藉由以不同方式將所述之各種層組合來達到，或層可基於設計、效能及成本因素而完全被省略。亦可包括未具體描述之其他層。可使用不同於彼等具體描述物質之物質。儘管本文中提供之許多實例描述各種層包含單一物質，但應瞭解，可使用物質之組合，諸如主體與摻雜物之混合物或更一般而言之混合物。又，該等層可具有各種子層。本文中給出之各種層之名稱不欲具有嚴格限制性。舉例而言，在裝置200中，電洞傳輸層225傳輸電洞且將電洞注入至發射層220中，且可 被描述為電洞傳輸層或電洞注入層。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"。如(例如)關於圖1及2所述，此有機層可包含單一層，或可另外包含具有不同有機物質之多個層。
亦可使用未具體描述之結構及物質，諸如包含諸如揭示於Friend等人之美國專利第5,247,190號(其全文係以引用的方式併入)中之聚合物質的OLED(PLED)。另外舉例而言，可使用具有單一有機層之OLED。例如，如Forrest等人之美國專利第5,707,745號(其全文係以引用的方式併入)中所述，OLED可經堆疊。OLED結構可自說明於圖1及2中之簡單層狀結構偏離。舉例而言，基板可包括成角反射表面以改良向外耦合，諸如如Forrest等人之美國專利第6,091,195號中所述之台面結構，及/或如Bulovic等人之美國專利第5,834,893號中所述之凹形結構，該等專利之全文係以引用之方式併入。
除非另外規定，否則各種實施例之層中任一者可藉由任何合適方法來沈積。對於有機層而言，較佳方法包括熱蒸鍍；諸如美國專利第6,013,982號及第6,087,196號(其全文係以引用的方式併入)中所述之噴墨；諸如Forrest等人之美國專利第6,337,102號(其全文係以引用的方式併入)中所述之有機氣相沈積(OVPD)及諸如美國專利申請案第10/233,470號(其全文係以引用的方式併入)中所述之藉由有機蒸氣噴印(OVJP)之沈積。其他合適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或惰性氣氛中進行。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經由遮罩沈積；諸如美國專利第6,294,398號及第6,468,819號(其全文係以引用的方式併入)中所述之冷焊及與一些諸如噴墨及OVJD之沈積方法相關之圖案化。亦可使用其他方法。待沈積之物質可經改質以使其與特定沈積方法相容。舉例而言，可將取代基(諸如分枝或未分枝且較佳含有至少3個碳之烷基及芳基)用於小分子中以增強其經受溶液處理之能力。可使用具有 20個或20個以上之碳之取代基，且3-20個碳為較佳範圍。具有不對稱結構之物質可具有比具有對稱結構之彼等物質更佳之溶液處理性，因為不對稱物質可具有較低之再結晶傾向。樹狀體取代基可用以增強小分子經受溶液處理之能力。
根據本發明之實施例製造之裝置可併入多種消費型產品中，包括平板顯示器、電腦監視器、電視、廣告牌、用於內部或外部照明及/或信號傳輸之燈、抬頭顯示器(heads up display)、完全透明顯示器、可撓性顯示器、雷射印表機、電話、手機、個人數位助理(PDA)、膝上型電腦、數位相機、可攜式攝像機、瞄準器、微顯示器、運載工具、大面積牆、劇院或運動場螢幕或標牌(sign)。各種控制機構可用以控制根據本發明製造之裝置，該等機構包括被動型矩陣及主動型矩陣。許多裝置意欲在對人類而言舒適之溫度範圍，諸如18℃至30℃，且更佳在室溫下(20-25℃)使用。
本文中描述之物質及結構可應用於不同於OLED之裝置中。舉例而言，諸如有機太陽能電池及有機光偵測器之其他光電裝置可採用該等物質及結構。更一般而言，諸如有機電晶體之有機裝置可採用該等物質及結構。
術語鹵基、鹵素、烷基、環烷基、烯基、炔基、芳烷基、雜環基、芳基、芳族基團及雜芳基於此項技術中已知，且係於以引用的方式併入之US 7,279,704第31-32欄中定義。
提供含二苯并[b,d]噻吩(本文中亦稱作"二苯并噻吩")之物質，其可用於藉由氣相沈積或溶液處理製造之PHOLED裝置，在低電壓下提供長壽命穩定裝置。可將物質用作PHOLED裝置中之穩定主體，或用於諸如強化層之其他層。
提供包含二苯并噻吩及/或二苯并呋喃之化合物。可將二苯并噻吩及二苯并呋喃用作電洞及/或電子傳輸有機導體，其通常在溶液中 展現比一些常見有機基團(諸如聯苯)更可逆之電化學還原。二苯并噻吩及二苯并呋喃之三重態能量相對較高。因此，可將含二苯并噻吩及/或二苯并呋喃之化合物有利地用作PHOLED裝置中之主體或強化層中之物質。舉例而言，二苯并噻吩之三重態能量對於用於藍色或綠色PHOLED裝置而言足夠高。含二苯并噻吩及/或二苯并呋喃之化合物可提供改良之裝置穩定性，同時維持優良裝置效率。
含二苯并噻吩之物質可具有以下通式結構：
R1及R2各自可獨立選自由下列各物組成之群：任何烷基、烷氧基、胺基、烯基、炔基、芳烷基、芳基、雜芳基及氫，且其中R1及R2可表示多個取代。
提供可有利地用於OLED之具有以下結構之特定二苯并噻吩化合物：
R1至R6各自係獨立選自由下列各物組成之群：任何烷基、烷氧基、胺基、烯基、炔基、芳烷基、芳基、雜芳基及氫，且其中R1至R6 各自可表示多個取代。
此外，提供可有利地用於OLED之特定含二苯并噻吩之化合物：
提供可有利地用於OLED之具有以下結構之含二苯并噻吩及/或含二苯并呋喃的化合物：
R1至R8各自獨立選自由下列各物組成之群：任何烷基、烷氧基、胺基、烯基、炔基、芳烷基、芳基、雜芳基及氫，且其中R1至R8各自可表示多個取代。
此外，提供可有利地用於OLED之含二苯并噻吩及/或含二苯并呋喃之化合物：
如本文中所使用，以下化合物具有以下結構：
亦提供用於OLED發射層之特定主體-摻雜物組合，其可產生具有特別優良特性之裝置。詳言之，表明具有使用H1作為主體及P1、P2或P7作為發射摻雜物之發射層之裝置具有特別優良之特性。如圖3中所說明，當發射層包括兩個有機層，第一有機層包括摻雜有P1之H1，且第二有機層包括摻雜有P2之H1時，該等裝置可特別有利。
類似地，具有使用化合物1作為主體及P3、P4及/或P5作為摻雜物之發射層之裝置可產生具有特別優良特性之裝置。詳言之，裝置具有使用化合物1作為主體及P3作為發射摻雜物之發射層，及/或使用化合物1作為主體及P4與P5作為摻雜物之具有多種摻雜物之發射層，其中P5為層中之主要發射摻雜物。如圖9中所說明，當發射層包括兩個有機層，第一有機層包括摻雜有P3之化合物1，且第二有機層包括摻雜 有P4及P5之化合物1時，該等裝置可特別有利。
具有使用化合物23作為主體及P1作為摻雜物之發射層之裝置亦可產生具有特別優良特性之裝置。
此外，消費型產品包含具有陽極、陰極及安置在陽極與陰極之間之有機層之裝置。該有機層另外包含含有選自由化合物2G-35G組成之群之化合物的物質，其中R1至R8獨立選自由下列組成之群：任何烷基、烷氧基、胺基、烯基、炔基、芳烷基、芳基、雜芳基及氫，且其中R1至R8各自可表示多個取代。
本文中所述之可用於有機發光裝置中之特定層之物質可與存在於裝置中之多種其他物質併用。舉例而言，本文中揭示之發射摻雜物可與存在之多種主體、傳輸層、阻擋層、注入層、電極及其他層併用。以下描述或提及之物質為可與本文中所揭示之化合物併用之物質的非限制性實例，且熟習此項技術者可易於查閱文獻來確認其他可併用之物質。
除本文中所揭示之物質以外及/或與本文中所揭示之物質併用，許多電洞注入物質、電洞傳輸物質、主體物質、摻雜物質、激子/電洞阻擋層物質、電子傳輸及電子注入物質亦可用於OLED。可與本文中所揭示之物質併用以用於OLED之物質的非限制性實例係列於下表1中。表1列出非限制性物質種類、用於各種類之化合物之非限制性實例及揭示該等物質之參考文獻。
實驗： 化合物實例
如下合成某些含二苯并噻吩之化合物：
步驟1.將3,3'-二羥基聯苯(9.3g，50mmol)溶解於100mL CH2Cl2中，隨後添加吡啶(15.8g，200mmol)。在-15℃下向此溶液中逐滴添加Tf2O(42.3g，150mmol)。將混合物於室溫下持續攪拌5h。將有機相分離且以鹽水洗滌一次。將粗產物以二氧化矽管柱進一步純化。獲得呈淺白色固體之3,3'-二三氟甲磺酸聯苯(21.3g)。
步驟2.向500mL圓形燒瓶中添加3,3'-二三氟甲磺酸聯苯(2.7g，6mmol)、4-二苯并噻吩 酸(4.1g，18mmol)、Pd2(dba)3(0.2g，0.2mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(0.3g，0.8mmol)、磷酸三鉀(5.1g，24mmol)及150mL甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，藉由矽膠管柱純化混合物。產量為2.6g。
向500mL圓形燒瓶中添加2,2'-二三氟甲磺酸聯苯(2.7g，6mmol)、4-二苯并噻吩 酸(4.1g，18mmol)、Pd2(dba)3(0.2g，0.2mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(0.3g，0.8mmol)、磷酸三鉀(5.1g，24mmol)及150mL甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，藉由矽膠管柱純化混合物。產量為2.5g。
向500mL圓形燒瓶中添加4,6-二碘基二苯并噻吩(4.2g，9.6 mmol)、4-二苯并噻吩 酸(5.3g，23.1mmol)、Pd2(dba)3(0.2g，0.2mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(0.3g，0.8mmol)、磷酸三鉀(7.4g，35mmol)及150mL甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，藉由矽膠管柱純化混合物。產量為2.4g。
向500mL圓形燒瓶中添加4,6-二碘基二苯并噻吩(3.9g，8.9mmol)、咔唑(3.3g，19.6mmol)、Pd2(dba)3(0.2g，0.2mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(0.3g，0.8mmol)、第三丁氧化鈉(5.8g，60mmol)及200mL二甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，藉由矽膠管柱純化混合物。產量為2.2g。
步驟1.將2,6-二溴-1,3,5-三甲基苯(8.34g，30mmol)溶解於50ml CHCl3中且與1.0g鐵粉一起懸浮於200mL圓底燒瓶中。在室溫下逐滴添加溴(2.00ml，31mmol)且將反應混合物加熱至回流持續3小時，冷卻至室溫且攪拌隔夜。將溶液傾析，以NaOH 10%水溶液洗滌，過濾 且蒸發。將固體殘餘物自氯仿結晶，提供7.00g黃色固體(2,4,6-三溴-1,3,5-三甲基苯)。
步驟2.向裝備有磁力攪拌器及回流冷凝器之1L圓底燒瓶中裝入2,4,6-三溴-1,3,5-三甲基苯(3.4g，9.5mmol)、4-二苯并噻吩 酸(8.7g，38mmol)、Pd2(OAc)2(0.16g，0.7mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(0.46g，1.1mmol)、磷酸三鉀(53g，250mmol)、1.2ml水及700mL甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，藉由矽膠管柱純化混合物。產量為5.2g。
向500mL圓形燒瓶中添加三聚氯化氰(1.5g，8.0mmol)、4-二苯并噻吩 酸(6.8g，30mmol)、Pd2(dba)3(0.2g，0.2mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(0.3g，0.8mmol)、磷酸三鉀(8.5g，40mmol)及250mL甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，過濾混合物。藉由自EtOAc再結晶將產物進一步純化。產量為3.0g。
在-78℃下以n-BuLi(己烷中1.6M，10mL，16mmol)處理150mL THF中的2,8-二溴苯并噻吩(2.5g，7.3mmol)歷時1h。逐滴添加40mL醚中二 基硼氟化物(5.0g，16.8mmol)。將混合物再攪拌1h後，使混合物緩慢溫至室溫且持續攪拌隔夜。藉由矽膠管柱純化產物。產量為2.8g。
將4-二苯并噻吩 酸(5.0g)懸浮於300mL二甲苯中且進行Dean-Stark萃取歷時5h。冷卻後，將固體收集，以EtOAc及己烷洗滌且在320℃下昇華兩次。產量為3.6g。
向500mL圓形燒瓶中添加醯胺鋰(0.2g，10mmol)、4-碘基二苯并噻吩(9.9g，32mmol)、Pd2(dba)3(0.2g，0.2mmol)、2-二環己基膦基-2',4',6'-三異丙基聯苯(0.4g，0.8mmol)、第三丁氧化鈉(2.9g，30mmol)及200mL甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，藉由矽膠管柱純化混合物。產量為4.0g。
向500mL圓形燒瓶中裝入30mL水中的2,3-二溴苯并[b]噻吩(5.0g，17.1mmol)、4-二苯并噻吩 酸(10.0g，43.8mmol)、Pd2(PPh3)4(0.8g，0.7mmol)、碳酸鉀(14.2g，103mmol)，隨後裝入200mL甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，分離含水相且蒸發，藉由矽膠管柱(己烷/乙酸乙酯4/1混合物)純化混合物，提供呈凝固無色油狀物之目標化合物(4.6g)。
步驟1.將二苯并噻吩(9.21g，50mmol)溶解於100ml無水THF中且將溶液冷卻至-50℃。逐滴添加n-BuLi(己烷中1.6莫耳溶液，40ml，64mmol)。將反應混合物溫至室溫，攪拌4小時且冷卻至-30℃。逐滴添加70ml THF中二苯并茀酮(9.0g，50mmol)，使反應混合物溫至室溫且攪拌隔夜。將反應混合物以乙酸乙酯(75ml)稀釋，以鹽水洗滌3次，經MgSO4乾燥，過濾且蒸發。藉由二氧化矽(己烷/乙酸乙酯7/3)管柱層析純化固體殘餘物，提供12.0g呈白色固體之9-(二苯并[b,d]噻吩-4-基)-9H-茀-9-醇。
步驟2.將9-(二苯并[b,d]噻吩-4-基)-9H-茀-9-醇(來自步驟1之產物，3.64g，10mmol)溶解於100ml無水甲苯中。在室溫下添加二十滴P2O5於CH3SO3H中之10%溶液，且將反應混合物攪拌5小時。將溶 液自固體殘餘物傾析，經由二氧化矽塞過濾且蒸發。使固體殘餘物經受管柱層析(二氧化矽、己烷/乙酸乙酯4/1)，提供4.0g白色固體。
步驟1.向裝備有回流冷凝器及磁性攪拌器之200ml圓底燒瓶中裝入咔唑(14.75g，88mmol)、3-碘溴苯(25.0g，88mmol)、Pd2(dba)3(0.8g，0.85mmol)及dppf(1,1'-雙(二苯基膦基)二茂鐵，0.98g，1.8mmol)、第三丁氧化鈉(25g，265mmol)及100ml無水二甲苯。使反應混合物在N2氣氛下回流48小時，冷卻至室溫且蒸發。使固體殘餘物經受二氧化矽管柱層析(溶離劑-己烷/乙酸乙酯9/1)，提供11.7g呈白色固體之9-(3-溴苯基)-9H-咔唑。
步驟2.將9-(3-溴苯基)-9H-咔唑(11.7g，36mmol)、雙(頻哪醇根基)二硼(13.85g，54mmol)、乙酸鉀(7.00g，71mmol)、1,1'-雙(二苯基膦基)二茂鐵]二氯鈀(II)(0.6g)溶解於100ml無水二噁烷中且在N2氣氛下回流隔夜。將反應混合物冷卻至室溫，以乙酸乙酯稀釋，以鹽水洗滌，經硫酸鎂乾燥且蒸發。使固體殘餘物經受二氧化矽管柱層析(溶離劑，己烷/乙酸乙酯5/1)，提供8.00呈黃色固體之9-(3-(4,4,5,5-四甲基-1,3,2-二氧硼 -2-基)苯基)-9H-咔唑。可藉由自己烷結晶來製備分析純物質，否則在無額外純化下使用產物。
步驟3.將2-溴大茴香醚(5.61g，30mmol)及4-二苯并噻吩 酸(6.84g，30mmol)、Pd2(PPh3)4(1.00g，0.8mmol)溶解於100ml甲苯中。添加碳酸鈉之飽和溶液(水中12.5g)且在N2氣氛下加熱反應混合物至回流隔夜。接著，將反應混合物冷卻至室溫，分離有機相且蒸發 甲苯。使固體殘餘物經受二氧化矽管柱層析(溶離劑-己烷/乙酸乙酯4/1)，提供呈6.6g無色凝固油狀物之4-(2-甲氧基苯基)二苯并[b,d]噻吩。
步驟4.將4-(2-甲氧基苯基)二苯并[b,d]噻吩(6.6g，23mmol)與鹽酸吡錠(27g，230mmol)混合在一起，置放於100ml圓底燒瓶中且加熱至回流持續45min。使反應混合物冷卻至60℃，以100ml水稀釋且以乙酸乙酯萃取。將有機相分離，經硫酸鎂乾燥，過濾且蒸發。使殘餘物經受二氧化矽管柱層析(溶離劑-己烷/乙酸乙酯5/1)，提供4.00g呈透明凝固油狀物之2-(二苯并[b,d]噻吩-4-基)苯酚。
步驟5.將2-(二苯并[b,d]噻吩-4-基)苯酚(3.9g，14mmol)溶解於80ml含有5ml無水吡啶之無水二氯甲烷中，且將溶液在冰浴中冷卻。逐滴添加三氟甲磺酸酐(5ml，28mmol)，將反應混合物在室溫下攪拌隔夜，以水洗滌且蒸發。以二氧化矽管柱層析純化殘餘物(溶離劑-己烷/乙酸乙酯9/1)，提供4.2g透明無色凝固油狀物。
步驟6.在具有回流冷凝器及磁力攪拌器之200ml圓底燒瓶中裝入來自步驟5之三氟甲磺酸鹽(4.1g，10mmol)及來自步驟2之 酸酯(3.7g，10mmol)，隨後添加磷酸三鉀(6.36g，30mmol)、乙酸鈀(0.67g，0.3mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(0.8g，0.6mmol)、200ml甲苯及6ml水。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，藉由使用溶離劑己烷/乙酸乙酯4/1之矽膠管柱純化混合物，提供2.8g呈白色固體之目標化合物。
向500mL圓形燒瓶中添加咔唑(3.7g，22mmol)、2,8-二溴苯并噻吩(3.4g，10mmol)、Pd(OAc)2(0.1g，0.5mmol)、三第三丁基膦(甲苯中1M，1.5mL，1.5mmol)、第三丁氧化鈉(6.3g，66mmol)及200mL二甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，以矽膠管柱純化混合物。產量為4.7g。
向500mL圓形燒瓶中添加4-碘基二苯并噻吩(6.2g，20mmol)、咔唑(4.0g，24mmol)、Pd2(dba)3(0.9g，1.0mmol)、2-二環己基膦基-2',6'-二甲氧基聯苯(1.6g，4.0mmol)、第三丁氧化鈉(5.8g，60mmol)及200mL二甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，以矽膠管柱純化混合物。產量為2.4g。
在0℃下，在氮下以n-BuLi(己烷中1.6M，48mL，76mmol)處理200mL無水DME中之間碳硼烷(5.0g，35mmol)歷時30分鐘。使混合物溫至室溫後，添加CuCl(9.5g，96mmol)。持續攪拌混合物達1h且添加30mL無水吡啶、4-碘基二苯并噻吩(22.6g，73mmol)。使所得混合物回流60h。冷卻後，以矽膠管柱純化混合物。產量為1.8g。
步驟1.在-50℃下，以n-BuLi(己烷中1.6M，100mL，160mmol)緩慢處理400mL THF中的二苯并噻吩(27g，147mmol)。使所得混合物緩慢溫至室溫且持續攪拌5h。使溶液冷卻回-78℃，緩慢添加100mL THF中的DMF(61mL)。在此溫度下再持續攪拌混合物2h且接著使其溫至室溫。將產物以EtOAc萃取且以矽膠管柱進一步純化。4-二苯并噻吩醛之產量為21g。
步驟2.在-78℃下向2,8-二溴二苯并噻吩(3.4g，10mmol)之300mL THF溶液中緩慢添加n-BuLi(己烷中1.6M，13.8mL，22mmol)。在此溫度下攪拌1h後，以4-二苯并噻吩醛(4.2g，20mmol)之100mL THF溶液緩慢處理混合物。接著使混合物溫至室溫。將產物以EtOAc萃取且以矽膠管柱進一步純化。二甲醇中間物之產量為4.2g。
步驟3.向以上二甲醇中間物(4.5g，7.4mmol)及CF3COOH(60mL)之50mL CH2Cl2溶液中逐份添加硼氫化鈉之固體粉末(2.8g，74mmol)。將混合物在氮下攪拌隔夜。以rotovap移除溶劑，且將固體以水洗滌，接著以NaHCO3溶液洗滌。以矽膠管柱進一步純化粗產物。最終產物之產量為2.4g。
在-50℃下，以n-BuLi(己烷中1.6M，50mL，80mmol)緩慢處理200mL THF中之二苯并噻吩(14g，76mmol)。使所得混合物緩慢溫至室溫且持續攪拌5h。使溶液冷卻回-78℃，緩慢添加SiCl4(2.0g，12mmol)。在此溫度下再持續攪拌混合物2h且在室溫下攪拌12h。將產物以EtOAc萃取且以矽膠管柱進一步純化。產量為3.5g。
向500mL圓形燒瓶中添加3,6-二(9-咔唑基)咔唑(3.0g，6mmol)，類似於以上關於3-(9-咔唑基)咔唑所述製備)、2-溴苯并噻吩(2.1g，7.8mmol)、CuI(0.4g，2.0mmol)、反-1,2-二胺基環己烷(0.4g，3.6mmol)、磷酸三鉀(3.2g，15mmol)及250mL甲苯。將反應加熱至回流且在氮氣氛下攪拌24小時。冷卻後，以矽膠管柱純化混合物。產量為3.1g。
向裝備有磁力攪拌器及回流冷凝器之300mL圓底燒瓶中裝入咔唑(7.1g，42.5mmol)、3-碘溴苯(25.00g，88mmol)、Pd2(dba)3(800mg，1mol%)、dppf(1',1'-雙(二苯基膦基)二茂鐵(975mg，2mol%)、第三丁氧化鈉(6.3g)及間二甲苯(100ml)。將反應混合物加熱至回流且在氮氣氛下攪拌48小時。接著使反應冷卻至室溫，經由二氧化矽塞過濾且蒸發。使殘餘物經受矽膠管柱層析(溶離劑梯度混合物，己烷-己烷/乙酸乙酯混合物9：1)，提供7.00g呈白色固體之9-(3-溴-苯基)-9H-咔唑，結構係以NMR及GCMS質譜分析確認。
將7.00g 9-(3-溴-苯基)-9H-咔唑(21.7mmol)、雙頻哪醇根基二硼烷(8.3g，32.7mmol)、乙酸鉀(4.30g)及(1,1'-雙(二苯基膦基)-二茂鐵)二氯鈀(II)(500mg)溶解於100ml二噁烷中且在氮下回流24小時。蒸發後，使殘餘物經受矽膠管柱層析(溶離劑，己烷/乙酸乙酯9/1混合物)，提供呈白色固體之純9-[3-(4,4,5,5-四甲基-[1,3,2]二氧硼 -2-基)-苯基]-9H-咔唑(11.8g)。
向裝備有磁力攪拌器及回流冷凝器之300mL圓底燒瓶中裝入2,8-二溴-二苯并噻吩(3.42g，10mmol)、9-[3-(4,4,5,5-四甲基-[1,3,2]二氧硼 -2-基)-苯基]-9H-咔唑(11.7g，30mmol)、乙酸鈀(II)(64mg)、2-二環己基膦基-2',6'-二甲氧基聯苯(234mg)、無水磷酸三鉀(53.0g)、700ml甲苯及2ml水。將反應混合物加熱至回流且在氮氣氛下攪拌24小時。接著使反應冷卻至室溫，經由二氧化矽塞過濾且蒸發。將殘餘物以己烷、乙醇、水、乙醇及己烷洗滌，接著由甲苯結晶。昇華(255℃，在10-5mm Hg下)提供純物質(白色固體，2.0g，結構係以NMR確定)。
將2,6-二甲氧基苯胺(5.5g，0.036mol)、2,2'-二溴聯苯(13.45g，0.043mol)、第三丁氧化鈉(8.58g，0.089mol)及Pd2(dba)3(1.15g，13mmol)裝入具有300mL無水甲苯之500mL 3頸燒瓶中。將此燒瓶抽空且以N2回填(此程序總共重複3次)。最後，將甲苯中1.0M(9.6mL，96mmol)P(t-Bu)3經由隔膜注入反應容器中。將反應混合物在回流下加熱18h。接著停止加熱。將反應混合物以200mL水稀釋。分離甲苯層。將含水相以200mL甲苯萃取一次。將甲苯萃取物合併，經硫酸鎂乾燥，接著過濾且在真空下濃縮。將粗產物矽膠層析。所使用之溶劑系統為20-35%二氯甲烷/己烷。
將9-(2,6-二甲氧基苯基)-9H-咔唑(10.00g)及吡錠鹽酸鹽(50.0g)置放於裝備有磁力攪拌器且浸沒於預熱油浴(230℃，45min)中之250ml圓底燒瓶中。將反應混合物冷卻至室溫，以400ml水稀釋且以乙酸乙酯(3×150ml)萃取。將有機部分合併，經無水硫酸鈉乾燥，過濾且蒸發，提供5.5g純2-咔唑-9-基-苯-1,3-二醇。將2-咔唑-9-基-苯-1,3-二醇(5.5g，20mmol)及吡啶(6.0ml)溶解於50ml DCM(無水)中且於冰浴中冷卻。在強力攪拌下逐滴添加三氟甲磺酸酐(6.0ml)於20ml DCM中之溶液，使反應混合物溫至室溫且攪拌隔夜。將反應混合物 以水洗滌，經硫酸鈉乾燥，過濾且蒸發，提供粗三氟甲磺酸鹽。以矽膠管柱層析(溶離劑-己烷/乙酸乙酯1/1混合物)獲得純物質(白色固體，6.0g)。
將雙三氟甲磺酸鹽(3.13g，5.8mmol)、4-二苯并噻吩 酸(3.30g，14.5mmol)、Pd2(dba)3(212mg，2mol%)、2-二環己基膦基-2',6'-二甲氧基聯苯(190mg，4mol%)、單水合磷酸三鉀(8.00g)、100ml甲苯及1ml水在氮氣氛下於圓底燒瓶中回流24小時，經由二氧化矽塞熱過濾，且蒸發。將殘餘物以己烷、乙醇、水、乙醇及己烷洗滌，接著自甲苯結晶，提供純物質(4.1g)。
將2,6-二甲氧基苯酚(15.4g，0.1mol)及15ml吡啶溶解於150ml DCM中且將溶液於冰浴中冷卻。在用力攪拌下逐滴添加三氟甲磺酸酐，使反應混合物溫至室溫，以水洗滌且蒸發。Kugelrohr蒸餾 (200℃，2mm Hg)提供25g凝固透明油狀物。
將2,6-二甲氧基三氟甲磺酸鹽(8.58g，30mmol)、4-二苯并噻吩 酸(6.84g，30mmol)、單水合磷酸三鉀(20.7g)、乙酸鈀(II)(672mg)、2-二環己基膦基-2',6'-二甲氧基聯苯(700mg)及150ml甲苯及3ml水加熱至回流且在氮氣氛下攪拌24小時。將熱反應混合物經由二氧化矽塞過濾且蒸發，使殘餘物經受二氧化矽管柱層析(溶離劑-己烷/乙酸乙酯4/1混合物)，提供4-(2,6-二甲氧基苯基)-二苯并噻吩(9.00g，來自乙酸乙酯之稜柱晶體)。
將4-(2,6-二甲氧基苯基)-二苯并噻吩(9.00g)及吡錠鹽酸鹽(20g)置放於裝備有磁力攪拌器之100mL圓底燒瓶中。將燒瓶浸沒於預熱油浴(220℃，1小時)中，冷卻至室溫且溶解於200ml水中。將溶液以乙酸乙酯(4×50mL)萃取，將有機部分合併，經硫酸鈉乾燥，過濾且蒸發，提供2-(二苯并[b,d]噻吩-4-基)苯-1,3-二醇(7.2g，白色固體)。
將2-(二苯并[b,d]噻吩-4-基)苯-1,3-二醇(7.2g)溶解於含有15mL吡啶之150mL無水DCM中。將溶液於冰浴中冷卻，接著逐滴添加三氟甲磺酸酐(25mL DCM中18mL)。使反應溫至室溫且以水中10%重碳酸鈉溶液洗滌。將DCM蒸發，且使殘餘物經受管柱層析，提供14.5g雙三氟甲磺酸鹽。
將三氟甲磺酸鹽(5.56g，10mmol)、4-二苯并噻吩 酸(5.35g，25mmol)、乙酸鈀(II)(44mg)、2-二環己基膦基-2',6'-二甲氧基聯苯(161mg)及三水合磷酸三鉀(7.00g)懸浮於100ml甲苯中且在氮氣氛下回流24小時。將熱反應混合物過濾且蒸發，使殘餘物自甲苯結晶兩次。昇華(245℃，10-5mm Hg)提供5.0g目標化合物。
在裝備有回流冷凝器及磁力攪拌器之300ml圓底燒瓶中裝入2,6-二甲氧基三氟甲磺酸鹽(10.00g，35mmol)、苯基 酸(4.25g，35mmol)、單水合磷酸三鉀(24.1g)、乙酸鈀(II)(156mg，2mol%)、2-二環己基膦基-2',6'-二甲氧基聯苯(573mg，4mol%)、甲苯(100ml)及水(2ml)。將反應混合物回流隔夜，經由二氧化矽塞過濾並使液體蒸發。將殘餘物以矽膠管柱層析(溶離劑為己烷/乙酸乙酯4/1混合物)，得到呈白色固體之二甲氧基聯苯(5.00g)。
將2,6-二甲氧基聯苯(5.00g)及15g吡錠鹽酸鹽置於圓底燒瓶中，並浸沒於油浴(210℃，1.5小時)中。接著使反應物冷卻至室溫，以200ml水稀釋並以乙酸乙酯(4×50ml)萃取。將有機溶離份合併，以硫酸鈉乾燥並使液體蒸發乾。將殘餘物以矽膠管柱層析(溶離劑為己烷/乙酸乙酯1/1混合物)，得到3.3g呈黃色固體之聯苯-2,6-二醇。
將聯苯-2,6-二醇(7.2g，39mmol)溶解於DCM(100ml)及吡啶(10ml)中。將溶液於冰浴中冷卻，且在用力攪拌下逐滴添加三氟甲磺酸酐(27.3g)。使反應混合物回溫至室溫，以水洗滌，乾燥並使液體蒸發。將殘餘物以矽膠管柱層析(溶離劑為己烷/乙酸乙酯4/1混合物)，得到8.00g純三氟甲磺酸鹽。
將三氟甲磺酸鹽(7.4g，16.4mmol)、4-二苯并噻吩 酸(11.2g，49mmol)、單水合磷酸三鉀(22.7g)、乙酸鈀(II)(70mg)、2-二環己基 膦基-2',6'-二甲氧基聯苯(270mg)及100ml甲苯在氮氣氛圍下回流隔夜。將熱溶液經由二氧化矽塞過濾並使液體蒸發。將殘餘物以己烷/乙酸乙酯結晶，得到呈白色固體之目標產物(5.01g)。另外藉由昇華純化物質(220℃，10-5mm Hg)。
向裝備有回流冷凝器及磁力攪拌器之300ml圓底燒瓶中裝入2-溴苯胺(8.00g，46.5mmol)、4-二苯并噻吩 酸(10.5g，46.5mmol)、碳酸鉀(20g，水中飽和溶液)、肆(三苯基膦)鈀(0)(500mg)及100ml甲苯。將反應混合物在氮氣氛下回流隔夜，經由二氧化矽塞過濾且蒸發。以矽膠管柱層析(溶離劑，己烷/乙酸乙酯4/1混合物)純化產物，提供呈黃色油狀物之2-(二苯并[b,d]噻吩-4-基)苯胺(10.1g)。
將2-(二苯并[b,d]噻吩-4-基)苯胺(10.1g，36.4mmol)、2,2'-二溴聯苯(12.0g，38.5mmol)、第三丁氧化鈉(7.00g，72.9mmol)及Pd2(dba)3(330mg)裝入具有300mL無水甲苯之500mL 3頸燒瓶中。將此燒瓶抽空且以N2回填(重複此程序總共3次)。最後，將甲苯中1.0M(5mL，96mmol)P(t-Bu)3經由隔膜注射入反應容器中。將反應混合物在回流下加熱18h。接著停止加熱。將反應混合物以200mL水稀釋。分離甲苯層。將含水相以200mL甲苯萃取一次。將甲苯萃取物合併，經硫酸鎂乾燥，接著過濾且在真空下濃縮。將原料以己烷洗滌 且自甲苯-DCM結晶。另外藉由昇華(190℃，10-5mm Hg)純化物質，提供6.23g純晶體物質。
向裝備有磁力攪拌器及回流冷凝器之300mL圓底燒瓶中裝入2,6-二溴吡啶(2.20g，9.2mmol)、4-二苯并噻吩 酸(4.62g，20mmol)、Pd2(dba)3(180mg)、S-phos(220mg)、三磷酸鉀(6.00g)及100mL無水甲苯。以氮填充燒瓶且將溶液在回流下攪拌隔夜。接著將熱反應混合物經由二氧化矽塞過濾，以熱甲苯洗滌二氧化矽。將有機部分合併且蒸發。使殘餘物經受矽膠管柱層析(溶離劑，己烷/乙酸乙酯4/1混合物)，提供呈白色固體之目標化合物(3.01g)。將物質另外藉由昇華(225℃，10-5mm Hg)純化，且用於裝置製造。
裝置實例
所有實例裝置係藉由高真空(<10-7Torr)熱蒸鍍製造。陽極電極為約800Å，1200Å或2000Å氧化銦錫(ITO)，或800Å藍寶石/IZO。陰極係由10Å LiF，隨後1000Å Al組成。在製造後，即刻將所有裝置用以環氧樹脂密封之玻璃蓋封裝於氮手套箱中(<1ppm之H2O及O2)，且將吸濕劑併入包裝內部。
裝置實例1-8之有機堆疊係依次由ITO表面(1200Å)；作為電洞注入層(HIL)之100Å P1；作為電洞傳輸層(HTL)之300Å 4,4'-雙[N-(1-萘基)-N-苯基胺基]聯苯(α-NPD)；作為發射層(EML)之300Å摻雜有10或15wt% Ir磷光化合物之本發明化合物；作為ETL2之50Å或100Å HPT或本發明化合物及作為ETL1之400或450Å參-8-羥基喹啉鋁(Alq3)組成。
類似於裝置實例，但將CBP用作主體來製造比較實例1。
將裝置實例1-8中用於發射層之物質，及ETL2及ETL1之物質及厚度提供於表2中。測試裝置，且將所量測之結果提供於表3中。使用術語Cmpd來縮寫化合物。
由裝置實例1-8可見本發明化合物作為綠色磷光OLED中之主體提供高裝置效率(在1000cd/m2下LE>35cd/A)，表示作為發色團之二苯 并噻吩具有對於有效綠色電致磷光而言足夠高之三重態能量。最顯著為併入化合物1作為主體之裝置之高穩定性。裝置實例3與比較實例1僅在主體中不同。裝置實例3使用化合物1作為主體，而比較實例1使用常用主體CBP。壽命，T80%(定義為在室溫下，在40mA/cm2之恆定電流密度下，初始亮度L0衰減至其值之80%所需之時間)分別為300小時及105小時，其中裝置實例3具有略微較高之L0。可將其解釋為裝置穩定性的幾乎3倍改良。本發明化合物可良好地用作強化層(ETL2)。裝置實例1及裝置實例3皆將化合物1作為主體，但分別將化合物1及2,3,6,7,10,11-六苯基聯伸三苯(HPT)作為強化層。其在類似L0(約13600cd/m2)下分別具有325及300小時之T0.8，表示本發明化合物作為強化層之優良效能。
資料表明芳基苯并噻吩(尤其為經聯苯取代之二苯并噻吩)為用於磷光OLED之極佳主體及強化層，提供與常用CBP作為主體相比至少相同效能及多倍穩定性改良。
製造具有兩個不同經摻雜發射層之許多裝置，其中裝置不包括使用諸如NPD之物質之電洞傳輸層。表4展示用於此等裝置之結構。表5展示用於此等裝置之經量測實驗結果。一般而言，裝置具有ITO陽極，LG101TM(購自LG Chemical，Korea)的電洞注入層，及具有第一有機層及第二有機層(其之間具有界面)之發射層。一些裝置具有強化層(ETL2)。所有裝置均具有可自與LG101相同來源獲得之LG201的電子傳輸層(ETL1)。裝置9-16具有使用相同非發射性物質及不同磷光物質之第一及第二有機層，其中第一有機層另外包括低能量發射性物質。所有裝置9-16均包括具有第一及第二有機層(其之間具有界面)之發射層。有所在此等裝置中，磷光物質之濃度在第一(更接近陽極)有機層中較高。裝置實例9-16之物質及厚度提供於表4中。測試裝置，且將所量測之結果提供於表5中。使用術語Cmpd來縮寫化合物。除非 另有說明，否則所有百分比為wt%。
由裝置實例9、10及11可見裝置效率隨P3濃度增加而減低，且裝 置隨P3濃度減低而CIE紅移。裝置實例9-11僅在發射化合物P3之濃度上不同(亦即裝置含有不同P3濃度)，因為所有裝置實例9-11均含有本發明化合物1作為主體，且在EML與LG201之間不具有阻擋層。
由裝置實例12、13及14可見裝置效率隨P3濃度增加而減低，且裝置隨P3濃度減低而CIE紅移，且裝置工作電壓隨P3濃度減低而增加。裝置12-14僅在發射性化合物P3濃度上不同，因為所有裝置12-14含有本發明化合物1作為主體且阻擋層位於EML與ETL之間。顯著地，化合物1為有效電子傳輸及阻擋層物質，因為展示裝置12、13及14各自之效率超過裝置9、10及11之效率。又，發現化合物1之電子穩定性較顯著，因為裝置12-14表明自1000cd/m2初始亮度起超過100000小時之LT60%穩定性。
由裝置實例15及16可見裝置在注入層LG101厚度變化(例如200Å對100Å)時展示裝置特徵(例如CIE，效率)之變化。
裝置實例17-20之有機堆疊依次由ITO表面；作為電洞注入層(HIL)之100Å P1；作為電洞傳輸層(HTL)之300Å NPD；作為發射層(EML)之300Å摻雜有10wt%或15wt% P1 Ir磷光化合物之本發明化合物；作為強化層(ETL2)之50Å或100Å HPT或本發明化合物；具有表5所識別之厚度之Alq3電子傳輸層(ETL1)及LiF/Al陰極組成。詳言之，BL及ETL具有總計500Å。因此，表5裝置之一般裝置結構為：ITO(1200Å)/P1(100Å)/NPD(300Å)/主體：P1 x%(300Å)/ETL2(50Å或100Å)/Alq3(400Å或450Å)/LiF(10Å)/Al(1000Å)。
表6中之資料描述裝置實例17-20之效能。電壓、發光效率、外量子效率及功率效率資料係在1000cd/m2(顯示水平亮度)下量測。壽命係在加速條件：40ma/cm2 DC下量測。亦將壽命測試條件(40mA/cm2)下初始裝置亮度(L0)展示於表5中。將化合物23用作綠色磷光發射體P1之主體。兩種不同摻雜物濃度(10%或15%)及兩個不同ETL1層(400Å或450Å之Alq3)在裝置中變化且經實驗測試。資料展示裝置效能無歸因於摻雜物濃度變化之顯著差異。然而，存在歸因於ETL1層變化之裝置效能差異。在具有HPT作為ETL1層之裝置中，裝置效率由於HPT之較強BL特性而略微較高。然而，具有化合物23作為ETL1之裝置壽命較長。資料表明化合物23可用作綠色磷光發射體之有效主體及裝置中之ETL1。具有化合物23作為裝置中之ETL1層之裝置穩定性高於具有類似整體結構，但使用HPT作為ETL1層之裝置的穩定性。
裝置實例21-24之有機堆疊依次由陽極表面；作為電洞注入層(HIL)之100Å P1或LG101；作為電洞傳輸層(HTL)之300Å NPD或無HTL；作為發射層(EML)之摻雜有9wt%、15wt%或20wt%P2或P7 Ir磷光化合物之300Å本發明化合物；作為強化層(ETL2)之50Å、150Å 或250Å H1；及作為電子傳輸層(ETL1)之200Å、300Å或400Å Alq3組成。裝置實例21-24之物質及厚度係提供於表7中。測試裝置，且將所量測之相應結果提供於表8中。
由裝置21、22、23及24可見，在具有含有H1及發射性化合物P2或P7之發射層之裝置結構之間展現差異。裝置實例21不具有HTL，且使用厚EML來增強裝置之操作穩定性。裝置實例21之經量測CIE座標並非藍色飽和，因此裝置實例22、23及24結構使用30nm EML。裝置實例22亦併入200nm ITO層以使裝置藍色CIE飽和。裝置實例23為未為操作穩定性而最佳化之標準藍色PHOLED。裝置實例24為使用與用於裝置實例23相同之發射化合物P7之藍色PHOLED。然而，裝置實例24具有使得能夠延長壽命之數種特徵，諸如無NPD、藍寶石散熱基 板、厚阻擋層及高發射體濃度。因此，裝置實例24之LT80%超過裝置實例23之LT80%，且裝置實例24與裝置實例23相比具有改良之藍色CIE。
圖3展示具有在發射層與陽極之間的高電洞導電率之唯一層，與用作發射層中非發射性主體相同的物質之強化層及具有第一及第二有機層(具有不同磷光物質及非發射性物質濃度，其中第二有機層中之磷光物質濃度不同)之發射層的有機發光裝置。圖3之裝置包括10nm厚之LG101電洞注入層，30nm厚之摻雜有30wt% P2之H1的第一有機發射層，30nm厚之摻雜有X wt% P2之H1的第二有機發射層，25nm厚之H1強化層，20nm厚之Alq3電子傳輸層，及LiF/Al陰極。在所製造之裝置中X自10wt%至18wt%變化，X=10、14及18wt%之裝置係如圖4圖例中所表示。
圖4展示圖3之裝置的正規化發光對時間之曲線圖。
圖5展示圖3之裝置的外量子效率對亮度之曲線圖。
圖6展示圖3之裝置的功率功效對亮度之曲線圖。
圖7展示圖3之裝置的亮度對電壓之曲線圖。
圖8展示圖3之裝置的EL強度對波長之曲線圖。
圖9展示具有在發射層與陽極之間的高電洞導電率之唯一層，與用作發射層中非發射性主體相同的物質之強化層及具有第一及第二有機層(在第一及第二有機層中具有不同磷光物質，其中第二有機發射層中之磷光物質濃度不同)之發射層的有機發光裝置。圖9之裝置包括10nm厚之LG101電洞注入層，30nm厚之摻雜有30wt% P1之H1第一有機發射層，30nm厚之摻雜有X wt% P2之H1第二有機發射層，25nm厚之H1強化層，20nm厚之Alq3電子傳輸層，及LiF/Al陰極。在所製造之裝置中X自10wt%至18wt%變化，X=10、14及18wt%之裝置係如圖4圖例中所表示。圖9之裝置與圖3之裝置極為類似，其差異在 於圖9裝置在第一及第二有機發射層中使用不同發射磷光物質，而圖3裝置於兩層中皆使用相同磷光物質。與圖9裝置相比，圖3裝置中磷光物質濃度相同。
圖10展示圖9之裝置的外量子效率對亮度之曲線圖。
圖11展示圖9之裝置的功率功效對亮度之曲線圖。
圖12展示圖9之裝置的亮度對電壓之曲線圖。
圖13展示圖9之裝置的EL強度對波長之曲線圖。
可將圖9之裝置與圖3之裝置比較。就裝置結構而言，裝置除發射層以外類似，其中圖9之裝置具有摻雜有磷光發射體P1之發射層及摻雜有磷光發射體P2之另一發射層，而圖3之裝置僅具有磷光發射體P2。兩個裝置皆具有摻雜物濃度步進，且即使在實際摻雜物不同之層中亦具有類似濃度。可由比較此等兩個裝置結構來理解若干點。第一，圖9之裝置展現為P1與P2之發射組合之寬發射譜。因此，可推斷圖3之裝置自摻雜有30% P2之層及摻雜有較低濃度P2之層發射。比較圖5與圖10可見，與圖3裝置之兩個數量級相比，由圖9裝置在三個數量級中外量子效率相對平坦所證明，圖9裝置具有比圖3裝置好的電荷平衡。
應瞭解，本文中所述之各種實施例僅為例示性的，且不欲限制本發明之範疇。舉例而言，本文中所述之許多物質及結構可在不偏離本發明精神下經其他物質及結構取代。因此，如熟習此項技術者顯而易見，所主張之本發明可包括來自本文所述之特定實例及較佳實施例之變化。應瞭解關於本發明為何起作用之各種理論不意欲為限制性的。

Claims (7)

  1. 一種有機發光裝置，其包含：一陽極；一陰極；一發射層；及一強化層，其中 係位於該強化層中；其中該發射層包含發射摻雜物，其包含： 其中R1、R2及R3各自獨立選自由下列所組成之群：任何烷基、烷氧基、胺基、烯基、炔基、芳烷基、芳基、雜芳基及氫。
  2. 如請求項1之有機發光裝置，其中(a)R1及R3形成稠合環，其視情況經進一步取代；(b)R2及R3形成稠合環，其視情況經進一步取代；或(c)兩者皆是。
  3. 如請求項2之有機發光裝置，其中R2及R3形成稠合環，其視情況經進一步取代。
  4. 如請求項3之有機發光裝置，其中該發射摻雜物包含：
  5. 如請求項3之有機發光裝置，其中該發射摻雜物包含：
  6. 如請求項2之有機發光裝置，其中該發射層包含H1作為主體。
  7. 如請求項2之有機發光裝置，其中該強化層為電洞阻擋層。
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US8007927B2 (en) 2011-08-30
US20160372685A1 (en) 2016-12-22
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