TWI531567B - 有機電發光材料及裝置 - Google Patents

有機電發光材料及裝置 Download PDF

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TWI531567B
TWI531567B TW104127754A TW104127754A TWI531567B TW I531567 B TWI531567 B TW I531567B TW 104127754 A TW104127754 A TW 104127754A TW 104127754 A TW104127754 A TW 104127754A TW I531567 B TWI531567 B TW I531567B
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mmol
compound
triphenyl
mixture
group
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TW201546056A (zh
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馬斌
吳永鋼
林世崇
鄺志遠
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環球展覽公司
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Description

有機電發光材料及裝置
本發明係關於具有苯并稠合噻吩及/或苯并稠合呋喃及聯伸三苯的新穎有機材料。特定言之，該等材料具有二苯并噻吩及/或苯并呋喃及聯伸三苯。該等材料可用於發光裝置(OLED)中。
本申請案主張2007年8月8日申請之美國臨時申請案第60/963,944號、2007年12月28日申請之美國臨時申請案第61/017,506號及2007年12月28日申請之美國臨時申請案第61/017,391號的優先權，該等案全文以引用方式特此併入本文中。本申請案亦與2007年12月28日申請的國際申請案第PCT/US07/89131號有關。
所主張之本發明係依據大學公司聯合研究協定由以下各方中之一或多者、以其之名義及/或與其相關而創制：University of Michigan、Princeton University、University of Southern California及Universal Display Corporation之董事。該協定在所主張之本發明創制之日及之前生效，且作為在該協定範圍內從事之活動之結果，創制所主張之本發明。
使用有機材料的光電裝置因多種原因而正日益變得符合需要。用於製造該等裝置的多種材料相對低廉，因此有機光電裝置具有優於無機裝置之成本優勢的潛力。此外，有機材料之內在特性(諸如其撓 性)可使其非常適於特殊應用，諸如製造於撓性基板上。有機光電裝置之實例包括有機發光裝置(OLED)、有機光電晶體、有機光電電池及有機光偵測器。對於OLED，有機材料可具有優於習知材料的效能優勢。舉例而言，有機發光層發光時的波長一般易用適當摻雜劑調節。
OLED使用當對裝置兩端施加電壓時發出光的有機薄膜。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。美國專利第5,844,363號、第6,303,238號及第5,707,745號描述數種OLED材料及構型，該等專利全文以引用方式併入本文中。
磷光發光分子之一應用為全色顯示器。該顯示器之工業標準需要經調適以發出特定顏色(稱為"飽和"色)的像素。特定而言，該等標準需要飽和紅色、綠色及藍色像素。可使用此項技術熟知的CIE座標度量顏色。
綠色發光分子之一實例為參(2-苯基吡啶)銥(表示為Ir(ppy)3)，其具有以下結構：
在此圖及本文中之以下圖式中，將氮與金屬(本文中為Ir)之配價鍵描繪為直線。
如本文中所使用，術語"有機"包括可用於製造有機光電裝置的聚合物材料以及小分子有機材料。"小分子"係指不為聚合物的任何有機材料，且"小分子"實際上可能相當大。在有些情況下，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不會將分子自"小分子"類別中移除。小分子亦可例如作為在聚合物主鏈上之側基或作為 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，樹狀體係由一系列建立於核心部分上之化學殼體組成。樹狀體之核心部分可為螢光或磷光小分子發光物。樹狀體可為"小分子"，且據信OLED領域中目前所用的所有樹狀體皆為小分子。
如本文中所使用，"頂"意謂離基板最遠，而"底"意謂最靠近基板。在第一層被描述成"配置於第二層上"的情況下，第一層係遠離基板配置。第一層與第二層之間可能存在其他層，除非明確說明第一層與第二層"接觸"。舉例而言，陰極可描述成"配置於"陽極上，即使其間存在多個有機層。
如本文中所使用，"溶液可處理"意謂能夠以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/或經液體介質沈積。
當據信配位基形成發光材料之光敏性質時，稱配位基為"光敏"配位基。
有關OLED之更多細節及上述定義可見於美國專利第7,279,704號中，該專利全文以引用方式併入本文中。
本發明提供含有聯伸三苯的苯并稠合噻吩化合物。該等化合物可用於有機發光裝置中。該等化合物尤其可用作有機發光裝置之發光層之主體、用作增強層之材料，或兩者。
含有聯伸三苯之苯并稠合噻吩的實例包括具有式(I)、式(II)及式(III)之結構的化合物：
R1、R2及R3獨立地選自烷基、烷氧基、胺基、烯基、炔基、芳烷 基、芳基、雜芳基及氫。R1、R2及R3各自可表示多個取代基。R1、R2及R3中至少一者包括聯伸三苯基團。聯伸三苯基團可與式(I)、(II)或(III)之結構直接連接，但聯伸三苯基團與式(I)、(II)或(III)之結構之間亦可存在"間隔基"。
含有聯伸三苯之苯并稠合噻吩或苯并稠合呋喃之實例包括具有以下結構的化合物：
X為S或O。較佳地，R1、R2及R3為獨立選自以下各基的非稠合取代基：CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1，或無取代。R1、R2及R3各自可表示單取代、二取代、三取代或四取代。n為1、2、3、4、5、6、7、8、9或10。Ar1及Ar2獨立地選自由苯、聯苯、萘、聯伸三苯、咔唑及其雜芳族類似物組成之群。R1、R2及R3中至少一者包括聯伸三苯基團。
有用之含聯伸三苯苯并稠合噻吩化合物及含聯伸三苯苯并稠合呋喃化合物之更特定實例包括如本文中所揭示之化合物1G-48G及化合物1-48。該等化合物可用作有機發光裝置之發光層之主體、該裝置之增強層材料，或兩者。
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‧‧‧電子障壁層
135‧‧‧發光層
140‧‧‧電洞障壁層
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‧‧‧倒置OLED
210‧‧‧基板
215‧‧‧陰極
220‧‧‧發光層
225‧‧‧電洞傳遞層
230‧‧‧陽極
圖1展示有機發光裝置。
圖2展示不具有單獨電子傳遞層的倒置有機發光裝置。
圖3展示含有聯伸三苯的苯并稠合噻吩及/或苯并稠合呋喃化合物。
一般而言，OLED包含至少一層配置於陽極與陰極之間且與陽極及陰極電連接的有機層。當施加電流時，陽極將電洞注入有機層中且陰極將電子注入有機層中。所注射之電洞及電子各自向帶相反電荷的電極遷移。當電子與電洞定位於同一分子上時，則形成"激子"，激子為具有激發能態的定域電子電洞對。當激子經由光電發射機制鬆馳時，發出光。在有些情況下，激子可定位於激生分子或激發複合體上。亦可存在非輻射機制，諸如熱鬆弛，但通常視為非所要的。
初期OLED使用例如美國專利第4,769,292號中所揭示之由其單重態發光("螢光")的發光分子，該專利全文以引用方式併入本文中。螢光發光一般在小於10奈秒之時段內發生。
最近，具有由三重態發光("磷光")之發光材料的OLED已得到證明。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期(1999)("Baldo-II")，該等文獻全文以引用方式併入本文中。磷光現象詳述於美國專利第7,279,704號之第5-6欄，其以引用方式併入本文中。
圖1展示有機發光裝置100。該等圖式未必依比例繪製。裝置100可包括基板110、陽極115、電洞注入層120、電洞傳遞層125、電子障壁層130、發光層135、電洞障壁層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的複合陰極。裝置100可藉由將所述層依序沈積來製造。該等不同層之性質及功能以及實例材料詳述於US 7,279,704之第6-10欄，其以引用方式併入本文中。
該等各層可存在更多實例。舉例而言，撓性透明基板-陽極組合揭示於美國專利第5,844,363號中，該專利全文以引用方式併入本文中。p-摻雜電洞傳遞層之實例為如美國專利申請公開案第2003/0230980號中所揭示之以50：1莫耳比摻有F4-TCNQ的m-MTDATA，該案全文以引用方式併入本文中。發光材料及主體材料之實例揭示於Thompson等人之美國專利第6,303,238號中，該專利全文以引用方式併入本文中。n-摻雜電子傳遞層之實例為如美國專利申請公開案第2003/0230980號中所揭示之以1：1莫耳比摻有Li的BPhen，該案全文以引用方式併入本文中。美國專利第5,703,436號及第5,707,745號揭示陰極之實例，其包括具有金屬(諸如Mg：Ag)薄層、上覆濺鍍沈積之透明導電性ITO層的複合陰極，該等專利全文以引用方式併入本文中。障壁層之理論及用途詳述於美國專利第6,097,147號及美國專利申請公開案第2003/0230980號中，該等專利全文以引用方式併入本文中。注入層之實例提供於美國專利申請公開案第2004/0174116號中，該案全文以引用方式併入本文中。保護層之說明可見於美國專利申請公開案第2004/0174116號中，該案全文以引用方式併入本文中。"增強層"在裝置中佔據的位置與上述障壁層位置相同，且可具有阻擋功能或改良裝置效能的其他功能。
圖2展示倒置OLED 200。該裝置包括基板210、陰極215、發光層220、電洞傳遞層225及陽極230。裝置200可藉由將所述層依序沈積來製造。由於最常見的OLED組態具有配置於陽極上方的陰極，且裝置200具有配置於陽極230下方的陰極215，因此裝置200可稱為"倒置"OLED。裝置200之對應層可使用與相對於裝置100所述類似的材料。圖2提供一如何可將裝置100之結構中之某些層省去的實例。
圖1及2中所說明的簡單層狀結構係作為非限制性實例提供，且應瞭解本發明之實施例可結合各種各樣的其他結構使用。所述特定材 料及結構具有示範性，且可使用其他材料及結構。功能性OLED可藉由將所述不同層以不同方法組合來獲得，或可基於設計、效能及成本因素將該等層一概省去。亦可包括未具體描述的其他層。可使用不同於具體所述材料的材料。儘管本文中所提供的多個實例將各層描述為包含單一材料，但應瞭解可使用材料組合，諸如主體與摻雜劑之混合物，或一般而言之混合物。此外，該等層可具有多個亞層。不希望本文中給不同層的命名具有嚴格限制性。舉例而言，在裝置200中，電洞傳遞層225傳遞電洞並將電洞注入發光層220內，且可描述為電洞傳遞層或電洞注入層。在一實施例中，OLED可描述為具有配置於陰極與陽極之間的"有機層"。此有機層可包含單層，或可進一步包含例如相對於圖1及圖2所述之不同有機材料之多層。
亦可使用未具體描述的結構及材料，諸如包含聚合物材料的OLED(PLED)，諸如Friend等人之美國專利第5,247,190號中所揭示，該專利全文以引用方式併入本文中。作為另一實例，可使用具有單有機層的OLED。OLED可例如如Forrest等人的美國專利第5,707,745號所述堆疊，該專利全文以引用方式併入本文中。OLED結構可不同於圖1及2所說明的簡單層狀結構。舉例而言，基板可包括改良外耦的角狀反射表面，諸如Forrest等人之美國專利第6,091,195號中所述的台式結構及/或如Bulovic等人之美國專利第5,834,893號中所述的坑形構造，該等專利全文以引用方式併入本文中。
除非另有說明，否則不同實施例之任何層可藉由任何適當方法沈積。對於有機層，較佳方法包括熱蒸發法、噴墨法(諸如美國專利第6,013,982號及第6,087,196號中所述，該等專利全文以引用方式併入本文中)、有機氣相沈積法(OVPD)(諸如Forrest等人之美國專利第6,337,102號中所述，該專利全文以引用方式併入本文中)，及藉由有機氣體噴印(OVJP)之沈積法(諸如美國專利申請案第10/233,470號所 述，該案全文以引用方式併入本文中)。其他適當沈積方法包括旋塗法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執行。對於其他層，較佳方法包括熱蒸發法。較佳圖案化方法包括經由光罩沈積法、冷焊法(諸如美國專利第6,294,398號及第6,468,819號中所述，該等專利全文以引用方式併入本文中)，及與某些沈積法(諸如噴墨及OVJD)相關的圖案化方法。亦可使用其他方法。可修改待沈積的材料以使其與特定沈積法相容。舉例而言，小分子中可使用支鏈或非支鏈且較佳含有至少3個碳的取代基(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個碳或20個碳以上的取代基，且3-20個碳為較佳範圍。與具有對稱結構的材料相比，由於不對稱材料可具有更低的再結晶傾向，因此具有不對稱結構的材料可具有更佳的溶液可處理性。樹狀體取代基可用於增強小分子經歷溶液處理的能力。
根據本發明之實施例製成的裝置可併入各種各樣的消費型產品中，包括平板顯示器、電腦監視器、電視、廣告牌、內部或外部照明燈及/或信號燈、抬頭顯示器、全透明顯示器、撓性顯示器、雷射印表機、電話、蜂巢式手機、個人數位助理(PDA)、膝上型電腦、數位式相機、錄像攝像機、取景器、微顯示器、載具、大面積牆、電影院或運動場螢幕或標牌。可使用不同控制機構(包括被動式矩陣及主動式矩陣)控制根據本發明所製成之裝置。很多裝置指定在人類舒適的溫度範圍內(諸如18攝氏度至30攝氏度)且更佳在室溫(20-25攝氏度)下使用。
本文中所述的材料及結構可應用於不同於OLED的裝置中。舉例而言，其他光電裝置(諸如有機太陽電池及有機光偵測器)可使用該等材料及結構。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。
術語鹵基、鹵素、烷基、環烷基、烯基、炔基、芳烷基、雜環 基團、芳基及雜芳基已為此項技術所知且定義於US 7,279,704之31-32欄中，其以引用方式併入本文中。
提供的化合物包含含有聯伸三苯的苯并稠合噻吩。聯伸三苯為三重態能量高、然而π-共軛作用高且第一單重態能階與第一三重態能階之間能量差較小的多芳族烴。此說明，與具有類似三重態能量的其他芳族化合物(例如聯苯)相比，聯伸三苯具有較易近接的HOMO能階及LUMO能階。使用聯伸三苯及其衍生物作為主體的優點在於，其可容納紅色、綠色及甚至藍色磷光摻雜劑以得到高效率而無能量淬滅。聯伸三苯主體可用於提供高效率及穩定性PHOLED。參見Kwong及Alleyene,TriphenyleneHosts in Phosphorescent Light Emitting Diodes,2006，第60頁，US 2006/0280965 A1。苯并稠合噻吩可用作電洞傳遞有機導體。此外，苯并噻吩(亦即：二苯并[b,d]噻吩(本文中稱"二苯并噻吩")、苯并[b]噻吩及苯并[c]噻吩)之三重態能量較高。苯并稠合噻吩與聯伸三苯之組合用作PHOLED中的主體可為有益的。更特定而言，苯并稠合噻吩通常傳遞電洞多於傳遞電子，而聯伸三苯傳遞電子多於傳遞電洞。因此，將該等兩部分組合成一個分子可提供經改良之電荷平衡，從而可改良壽命、效率及低電壓方面的裝置效能。該等兩部分之不同化學鍵聯可用於調節所得化合物之性質，以使得其最適於特定磷光發光物、裝置結構及/或製造方法。舉例而言，間伸苯基鍵聯有望形成更高的三重態能量及更高的溶解度，而對伸苯基鍵聯有望形成更低的三重態能量及更低的溶解度。
與苯并稠合噻吩之表徵類似，苯并稠合呋喃通常亦為具有較高三重態能量的電洞傳遞材料。苯并稠合呋喃之實例包括苯并呋喃及二苯并呋喃。因此，含有聯伸三苯與苯并呋喃的材料可有利地用作PHOLED中之主體或電洞障壁材料。含有該等兩種基團的化合物可提供經改良之電子穩定化作用，從而改良低電壓下之裝置穩定性及效 率。需要時，可藉由使用連接聯伸三苯及苯并呋喃的不同化學鍵聯調節含有聯伸三苯之苯并呋喃化合物之性質。
該等化合物可經不一定為聯伸三苯、苯并稠合噻吩及苯并稠合呋喃的基團取代。較佳地，用作化合物之取代基的任何基團具有高足以維持具有聯伸三苯苯并稠合噻吩或苯并稠合呋喃之益處的三重態能量(亦即，取代基之三重態能量維持苯并稠合噻吩、苯并稠合呋喃及聯伸三苯之高三重態能量)。可用作化合物之取代基之該等基團之實例可包括選自以下各基的任何取代基：CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1，或無取代，其中n為1、2、3、4、5、6、7、8、9或10，且其中Ar1及Ar2獨立地選自由以下各者組成之群：苯、聯苯、萘、聯伸三苯、咔唑及其雜芳族類似物。本文中所述的化合物具有足夠高的三重態能量以適用於具有磷光藍色發光材料的裝置中。
本文中所述化合物之取代基可未經稠合，以使得該等取代基不與該化合物之聯伸三苯、苯并稠合呋喃或苯并稠合噻吩部分稠合。取代基視情況可相互稠合(亦即，彼此間稠合)。
除裝置穩定性及效率提高外，本文中所提供的材料亦可在如藉由氣相沈積與溶液處理方法所製造之裝置中提供經改良之膜形成。特定而言，提供經改良之製造的材料具有中心吡啶環，苯并稠合伸噻吩與聯伸三苯或苯并呋喃與聯伸三苯連接至中心吡啶環。據信經改良之膜形成係化合物中極性環與非極性環組合所致。
含有聯伸三苯之苯并稠合噻吩的實例包括具有式(I)、式(II)及式(III)之結構的化合物：
R1、R2及R3獨立地選自烷基、烷氧基、胺基、烯基、炔基、芳烷基、芳基、雜芳基及氫。R1、R2及R3各自可表示多個取代基。R1、R2及R3中至少一者包括聯伸三苯基團。聯伸三苯基團可與式(I)、(II)或(III)之結構直接連接，但聯伸三苯基團與式(I)、(II)或(III)之結構之間亦可存在"間隔基"。
含有聯伸三苯之苯并稠合噻吩或苯并稠合呋喃之實例包括具有以下結構的化合物：
X為S或O。較佳地，R1、R2及R3為獨立選自以下各基的非稠合取代基：CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1，或無取代。R1、R2及R3各自可表示單取代、二取代、三取代或四取代。n為1、2、3、4、5、6、7、8、9或10。Ar1及Ar2獨立地選自由苯、聯苯、萘、聯伸三苯、咔唑及其雜芳族類似物組成之群。R1、R2及R3中至少一者包括聯伸三苯基團。
具有式(I)結構之化合物之實例包括：
R1至Rn獨立地表示選自烷基、烷氧基、胺基、烯基、炔基、芳烷 基、芳基及雜芳基的單取代、二取代、三取代或四取代，或無取代。
具有式(IV)結構之化合物之實例包括：
X為S或O。X較佳為S。R1至Rn獨立地選自由以下各者組成之群：CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1，或無取代。R1至Rn各自可表示單取代、二取代、三取代或四取代。n為1、2、3、4、5、6、7、8、9或10。Ar1及Ar2獨立地選自由苯、聯苯、萘、聯伸三苯、咔唑及其雜芳族類似物組成之群。R1、R2及R3中至少一者包括聯伸三苯基團。
具有式(II)結構之化合物之實例包括：
R1至Rn獨立地表示選自烷基、烷氧基、胺基、烯基、炔基、芳烷基、芳基及雜芳基的單取代、二取代、三取代或四取代，或無取代。
具有式(V)結構之化合物之實例包括：
X為S或O。X較佳為S。R1至Rn獨立地選自由以下各者組成之群：CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1，或無取代。R1至Rn各自可表示單取代、二取代、三取代或四取代。n為1、2、3、4、5、6、7、8、9或10。Ar1及Ar2獨立地選自由苯、聯苯、萘、聯伸三苯、咔唑及其雜芳族類似物組成之群。R1、R2及R3中至少一者包括聯伸三苯基團。
具有式(III)結構之化合物之實例包括：
R1至Rn獨立地表示選自烷基、烷氧基、胺基、烯基、炔基、芳烷基、芳基及雜芳基的單取代、二取代、三取代或四取代，或無取代。
具有式(VI)結構之化合物之實例包括：
X為S或O。X較佳為S。R1至Rn獨立地選自由以下各者組成之群：CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1，或無取代。R1至Rn各自可表示單取代、二取代、三取代或四取代。n為1、2、3、4、5、6、7、8、9或10。Ar1及Ar2獨立地選自由苯、聯苯、萘、聯伸三苯、咔唑及其雜芳族類似物組成之群。R1、R2及R3中至少一者包括聯伸三苯基團。
以上所揭示之各種含有聯伸三苯之苯并稠合噻吩可有利地用於有機發光裝置中。該等化合物尤其可在有機發光裝置中用作發光層之主體、該裝置之增強層材料，或兩者。
實驗
化合物實例
實例1 4-(聯伸三苯-2-基)二苯并噻吩(化合物1S)
1.合成2-溴聯伸三苯
以上化合物之合成說明於US20060280965中。
2.合成4-(聯伸三苯-2-基)二苯并噻吩
將4.4g(14.6mmol)2-溴聯伸三苯、4.0g(17.5mmol)4-二苯并噻吩酸、0.51g(0.44mmol)肆三苯膦鈀及4.0g(43.4mmol)碳酸鉀與90mL甲苯及10mL水饋入250mL圓底燒瓶中。將反應混合物用氮氣清洗30分鐘且接著在氮氣下、在攪拌下、加熱至回流隔夜。將反應混合物冷卻且將有機萃取物藉由柱層析及使用甲苯之再結晶加以純化。獲得5.1g(86%)白色固體產物，藉由質子NMR確認。
實例2 4-(3-(聯伸三苯-2-基)苯基)二苯并噻吩(化合物2S)
1.合成3-(2-聯伸三苯)苯基三氟甲磺酸酯
以上化合物之合成說明於臨時申請案第60/963,944號中。
2.合成4-(3-(聯伸三苯-2-基)苯基)二苯并噻吩
將4.52g(10.0mmol)3-(聯伸三苯-2-基)苯基三氟甲磺酸酯、3.0 g(13.0mmol)4-二苯并噻吩酸、0.46g(0.5mmol)Pd2(dba)3、0.82g(2.0mmol)2-二環己基膦基-2',6'-二甲氧基聯苯、12.7g(60.0mmol)K3PO4及150mL甲苯及15mL水饋入250mL圓底燒瓶中。在氮氣下、將反應混合物加熱至回流隔夜。將反應混合物冷卻且將有機萃取物藉由柱層析及再結晶加以純化。獲得4.3g(88%)白色固體產物，藉由質子NMR確認。
實例3 2,8-二(聯伸三苯-2-基)二苯并噻吩(化合物5S)
1.合成4,4,5,5-四甲基-2-(聯伸三苯-2-基)-1,3,2-二氧硼戊烷
此化合物之合成說明於US2006/0280965中。
1.合成2,8-二(聯伸三苯-2-基)二苯并噻吩
將2.25g(6.3mmol)4,4,5,5-四甲基-2-(聯伸三苯-2-基)-1,3,2-二氧硼戊烷、0.92g(2.7mmol)2,8-二溴二苯并噻吩、0.12g(0.14mmol)Pd2(dba)3、0.22g(0.53mmol)2-二環己基膦基-2',6'-二甲氧基聯苯、3.4g(16.0mmol)K3PO4、100mL甲苯及10mL水饋入250mL圓底燒瓶中。將反應混合物用氮氣清洗20分鐘且接著在攪拌下，加熱至回流隔夜。將反應混合物冷卻且過濾。將白色固體用甲醇洗滌3次(3×100 mL)及二氯甲烷(2×100mL)。獲得1.6g(94%產率)固體產物，將其藉由使用甲苯之再結晶及昇華進一步純化。產物藉由固體探針MS確認。
實例4 化合物20S
1.合成2-溴二苯并噻吩
將15g(79.9mmol)二苯并噻吩溶於1.5L氯仿中。向此溶液中逐滴添加12.76g(79.9mmol)溴。將反應混合物在室溫下劇烈攪拌2天且接著用亞硫酸鈉水溶液處理。將有機相蒸發以得到白色固體，基於GC-MS及HPLC結果，其具有48%未反應二苯并噻吩、50%之2-溴二苯并噻吩及約小於2%之2,8-二溴二苯并噻吩。使用乙酸乙酯將混合物重複再結晶以得到純2-溴二苯并噻吩。
2.合成硼酯產物
將8g(17.5mmol)3-(2-聯伸三苯)苯基三氟甲磺酸酯、9.1g(35.2mmol)雙(頻哪醇根基)二硼、290mg(0.35mmol)Pd(dffp)2Cl2、5.2g(52.5mmol)KOAc及150mL無水二噁烷饋入250mL三頸燒瓶中。將反應混合物在氮氣下加熱至90℃歷時20小時。用己烷中之30%乙酸乙酯作為溶離劑進行管柱層析之後，獲得7.0g白色固體。產物藉由質子NMR確認。
3.合成化合物20S
將2g(7.1mmol)2-溴二苯并噻吩、4.0g(9.3mmol)步驟2之硼酯產物、325mg(0.355mmol)Pd2(dba)3、582g(1.4mmol)S-phose、9g(42mmol)K3PO4、90mL甲苯及10mL水饋入250mL燒瓶中。將反應混合物在氮氣下加熱至回流隔夜。將反應混合物用二氯甲烷萃取且將有機萃取物藉由二氧化矽凝膠柱層析法及再結晶法純化。獲得約2.9g(85%)白色固體產物，產物藉由質子NMR確認。
實例5 化合物10S
1.合成4,4'-二甲氧基-鄰聯三苯
製備由1,2-二溴苯(50g，212mmol)、4-甲氧基苯基酸(78g，513mmol)、三苯膦(11.12g，42.2mmol)、碳酸鉀(73.25g，530mmol)、二甲氧基乙烷(290mL)與水(290mL)組成的混合物。將氮氣直接鼓入混合物中20分鐘。添加乙酸鈀(4.76g，21.2mmol)且將混合物在氮氣下加熱至回流隔夜。將反應混合物冷卻且添加水及二氯甲 烷。將各層分離且將水層用二氯甲烷萃取。將所組合之有機層經由矽藻土過濾且用鹽水洗滌，經硫酸鎂乾燥，過濾，蒸發，得到黑色油狀物。藉由使用己烷中之0至100%二氯甲烷溶離的柱層析法純化粗物質。使用Kugelrohr、在200至220℃下、藉由蒸餾將主要溶離份純化。獲得49g(80%)產物。
2.合成2,11-二甲氧基聯伸三苯
將12.4g(42.7mmol)4,4'-二甲氧基-鄰聯三苯及16g(63.0mmol)碘片置於250mL反應容器中。添加200mL甲苯，接著添加30mL環氧丙烷。裝設配有藉由循環冷卻器冷卻之冷凝器的光反應器。使用400W中壓汞燈作為光源。將反應容器置於櫥櫃中。點燈且將冷卻器溫度設置成使得離開反應器之水維持在20℃與25℃之間(藉由連接排出流之熱電偶監測)。反應進行18小時。濾出固體且用己烷洗滌，僅回收2.2g物質。將濾液用甲苯稀釋且用硫酸鈉溶液洗滌。將水層用甲苯反萃取，且將有機層經硫酸鎂乾燥，過濾且蒸發。將物質溶於甲苯中且添加亞硫酸鈉溶液並攪拌。將各層分離，用甲苯萃取水層，且將所組合之有機層經硫酸鎂乾燥，過濾且蒸發。藉由使用0至100%乙酸乙酯/己烷溶離的柱層析法純化殘餘物。獲得8.8g物質(72%)。
3.合成聯伸三苯-2,11-二醇
將2,11-二甲氧基聯伸三苯(8.8g，30.5mmol)與鹽酸吡啶(31.73g，274.6mmol)之混合物加熱至220℃歷時2小時。將混合物冷卻並添加水。將所得固體濾出，用水洗滌，且在高真空下乾燥。獲得7.45g(94%)所要產物。
4.合成聯伸三苯-2,11-二基雙(三氟甲磺酸酯)
將聯伸三苯-2,11-二醇(7.45g，28.62mmol)添加至100mL二氯甲烷及13mL吡啶中且將溶液於冰鹽浴中冷卻。在氮氣下，將70mL二氯甲烷中之三氟甲烷磺酸酐(19mL，114.49mmol)逐滴添加至該溶液中。使反應進行2小時且藉由添加甲醇及水、繼之用二氯甲烷稀釋來中止反應。濾出黃褐色固體並用二氯甲烷及水洗滌。將濾液中之各層分離並用二氯甲烷萃取水層。將有機萃取物經硫酸鎂乾燥，過濾並蒸發以得到褐色固體。將褐色固體如下純化：在170℃下昇華之後，進行柱層析(用0至100%二氯甲烷/己烷溶離)，且自300mL沸騰甲苯中再結晶兩次。獲得11.4g產物(76%)。
5.合成化合物10S
製備聯伸三苯-2,11-二基雙(三氟甲磺酸酯)(1.5g，2.9mmol)、二苯并噻吩-4-酸(2.6g，11.4mmol)、氟化鉀(1.1g，19mmol)與50mL THF之混合物。將氮氣直接鼓入混合物中1小時。接著，添加乙酸 鉀(13mg，0.06mmol)及參環己基膦(19mg，0.07mmol)，且接著將氮氣鼓入混合物中另30分鐘。將混合物在50℃下加熱隔夜。接著將反應物冷卻至室溫。藉由過濾收集沈澱物。將白色固體置於一索氏萃取器(soxhlet extractor)中且藉由回流THF洗滌隔夜。收集萃取器中之固體，得到0.9克白色固體(產率53%)。
實例6 化合物9S
1.合成2-(3'-甲氧基聯苯-3-基)聯伸三苯
稱取12.9g(28.5mmol)3-(聯伸三苯-2-基)苯基三氟甲磺酸酯、6.5g(42.8mmol)3-甲氧基苯基酸、0.47g(1.1mmol)2-二環己基膦基-2',6'-二甲氧基聯苯(SPhos)與18.2g(85.5mmol)磷酸三鉀(K3PO4)置於一圓底燒瓶中。將150mL甲苯及80mL水作為溶劑添加至燒瓶內。將溶液用氮氣清洗且添加0.26g(0.28mmol)參(二亞苄基丙酮)二鈀(0)[Pd2(dba)3]。將溶液加熱至回流溫度歷時12個小時。經冷卻，將有機層分離，且經MgSO4乾燥。產物易藉由使用己烷/二氯甲烷作為溶離劑(1/0至3/2梯度)的柱層析法分離。藉由旋轉蒸發移除溶劑，形成11.7g(28mmol)產物2-(3'-甲氧基聯苯-3-基)聯伸三苯。
2.合成3'-(聯伸三苯-2-基)聯苯-3-醇
在氮氣下，在圓底燒瓶中，將11.5g(28mmol)2-(3'-甲氧基聯苯-3-基)聯伸三苯及21.1g(183mmol)鹽酸吡啶加熱至204℃。冷卻後，添加水並用二氯甲烷萃取。將所組合之有機溶離份用額外水洗滌並藉由旋轉蒸發移除溶劑。將固體乾燥裝填於矽藻土上，且藉由使用己烷：二氯甲烷(1：4)作為溶離劑的柱層析法純化產物。藉由旋轉蒸發移除溶劑，形成8.6g(22mmol)產物3'-(聯伸三苯-2-基)聯苯-3-醇。
3.合成3'-(聯伸三苯-2-基)聯苯-3-基三氟甲磺酸酯
在氮氣下，將8.6g(22mmol)3'-(聯伸三苯-2-基)聯苯-3-醇與3.4g(43.4mmol)無水吡啶及450mL無水二氯甲烷一起添加至燒瓶中。將溶液於冰浴中冷卻且經由注射器緩慢添加12.2g(43.4mmol)三氟甲烷磺酸酐(Tf2O)。將溶液溫至室溫且攪拌隔夜。將溶液用水洗滌，經MgSO4乾燥且藉由旋轉蒸發移除溶劑。藉由使用己烷/二氯甲烷作為溶離劑(1/0至1/1梯度)的柱層析法純化產物3'-(聯伸三苯-2-基)聯苯-3-基三氟甲磺酸酯，形成10.7g(20.2mmol)產物。
4.合成化合物9S
將5.5g(10.4mmol)上述步驟3之產物、3.0g(13.5mmol)4-酸二苯并噻吩、458mg(0.5mmol)Pd2(dba)3、820mg(2mmol)S- phose、12.7g(60mmol)磷酸鉀及150mL甲苯添加至250mL燒瓶中。將反應混合物在氮氣下加熱至回流隔夜。接著將其冷卻並處理。使用己烷中之20%二氯甲烷作為溶離劑進行二氧化矽凝膠柱層析且接著用甲醇洗滌之後，獲得約5g白色產物。產物藉由質子NMR確認。
實例7 化合物19S
1.合成3,3'-二甲氧基-鄰聯三苯
將1,2-二溴苯(50.0g，0.212mol)、3-甲氧基苯基酸(77.3g，0.509mol)、乙酸鈀(1.2g，5.33mmol)、三苯膦(21.4mmol)、碳酸鈉(78.9g，0.744mol)與二甲氧基乙烷(430mL)及水(290mL)組合於2000mL圓底燒瓶(裝配有攪棒、回流冷凝器及氮氣進口)中並在回流溫度下加熱4天。添加乙酸乙酯(500mL)並將有機層分離，經硫酸鎂乾燥並蒸乾，得到61.3g(99.7%)白色固體狀之3,3'-二甲氧基-鄰聯三苯。
2.合成2,9-二甲氧基聯伸三苯
在2000mL圓底燒瓶(裝配有氮氣進口及攪棒)中，將3,3'-二甲氧基-鄰聯三苯(61.3g，0.211mol)溶於無水二氯甲烷(1000mL)中。接著添加氯化鐵(III)(68.6g，0.423mol)，並將混合物攪拌隔夜。次日 晨，再添加兩個當量的氯化鐵(III)，且反應在一小時內完成。將甲醇及水添加至混合物中且將有機層分離，經硫酸鎂乾燥，並蒸乾。將粗產物藉由使用60/40二氯甲烷/己烷作為溶離劑的二氧化矽凝膠柱層析法進行純化，得到50.7g淺黃色固體，將其自700mL乙腈中再結晶，得到49.1g之2,9-二甲氧基聯伸三苯。
3.合成2,9-二羥基聯伸三苯
將2,9-二甲氧基聯伸三苯(49.1g，0.170mol)及鹽酸吡啶(200g，1.70mol)置於裝配有攪棒、回流冷凝器及氮氣進口的500mL圓底燒瓶中且在220℃下加熱90分鐘。將溶液冷卻且添加水，引起白色沈澱物形成，藉由真空過濾收集，用水洗滌且真空乾燥，得到43.7g(96%)2,9-二羥基聯伸三苯。
4.合成聯伸三苯-2,7-二基雙(三氟甲磺酸酯)
在裝配有攪棒及氮氣進口的1000mL圓底燒瓶中，將三氟甲烷磺醯酐(38.7g，137mmol)逐滴添加至2,9-二羥基聯伸三苯(17.5g，65mmol)與吡啶(300mL)之經冷卻溶液(0℃)中。將反應混合物在室溫下攪拌隔夜。將吡啶蒸發之後，將所得固體與甲醇(500mL)一起攪拌且 藉由真空過濾收集，得到32g白色粉末，自500mL之30/70庚烷/二氯乙烷中再結晶，得到28.3g(82%)2,9-雙(三氟甲烷磺醯基)聯伸三苯。
5.合成化合物19S
製備聯伸三苯-2,7-二基雙(三氟甲磺酸酯)(2g，3.8mmol)、二苯并噻吩-4-酸(3.5g，15mmol)、氟化鉀(1.5g，25mmol)與THF 100mL之混合物。將氮氣直接鼓入混合物中1小時。接著，添加乙酸鉀(17mg，0.08mmol)及參環己基膦(26mg，0.09mmol)，且接著將氮氣鼓入混合物中另30分鐘。將混合物在室溫下攪拌兩天。接著將反應物冷卻至室溫。藉由過濾收集沈澱物。添加乙酸鉀(17mg，0.08mmol)及參環己基膦(26mg，0.09mmol)，且接著將氮氣鼓入混合物中另15分鐘。將混合物在室溫下另攪拌兩天。將灰色固體置於一索氏萃取器中且藉由回流THF洗滌隔夜。收集萃取器中之固體，得到2.1克白色固體(產率92%)。
實例8 化合物22S
步驟1
製備2,6-二氯吡啶(13g，88mmol)、二苯并噻吩-4-酸(5g，22mmol)、磷酸三鉀(28g，132mmol)、甲苯(300mL)與水(30mL)之混合物。將氮氣直接鼓入混合物中1小時。接著添加參(二亞苄基丙 酮)(0.54g，1.3mmol)，且接著將氮氣鼓入混合物中另20分鐘。將混合物在室溫下攪拌兩天。接著收集有機層並藉由二氯甲烷萃取水層。將所組合之有機層經硫酸鎂乾燥且濃縮。將粗產物藉由二氧化矽凝膠急驟層析(使用己烷中之至多10%乙酸乙酯)純化，得到5克黃色固體。自二氯乙烷/庚烷中進一步再結晶，獲得2.5克白色固體(39%)。
2.合成化合物22S
製備4,4,5,5-四甲基-2-(聯伸三苯-2-基)-1,3,2-二氧硼戊烷(2.2g，6.1mmol)、2-氯-6-(二苯并噻吩-4-基)吡啶(1.5g，5.1mmol)、磷酸三鉀(3.3g，15.3mmol)、甲苯(150mL)與水(15mL)之混合物。將氮氣直接鼓入混合物中40分鐘。接著，添加參(二亞苄基丙酮)二鈀(56mg，0.06mmol)與雙(環己基)-2-二苯基膦(100mg，0.24mmol)，且接著將氮氣鼓入混合物中另17分鐘。將反應混合物在氮氣下回流隔夜。藉由過濾收集沈澱物且藉由甲苯、二氯甲烷及甲醇洗滌。接著將產物溶於250mL沸騰二甲苯中，經由小硫酸鎂柱塞過濾。將濾液加熱至回流以將所有固體溶解，且讓其緩慢冷卻。獲得2.3克白色固體狀之再結晶產物(93%)。
實例9 化合物21S
1.合成2-氯-6-(3-甲氧基苯基)吡啶
製備間甲氧基-苯基酸(10g，65.8mmol)、2,6-二氯吡啶(9.7 g，65.8mmol)、碳酸鉀(27.3g，197.4mmol)、三苯膦(2.07g，7.9mmol)、二甲氧基乙烷(250mL)及水(80mL)之混合物。將氮氣直接鼓入混合物中20分鐘。接著添加乙酸鈀(0.44g，2.0mmol)。再次將氮氣鼓入混合物中另10分鐘。將混合物在氮氣下加熱至回流隔夜。將反應混合物冷卻至室溫。將有機層分離且將水層用二氯甲烷萃取。將所組合之有機層經硫酸鎂乾燥，過濾且蒸發。將混合物藉由二氧化矽管柱(使用己烷中之至多10%乙酸乙酯)純化，得到6.5g無色油狀物(45%)。
2.合成2-(二苯并[b,d]噻吩-4-基)-6-(3-甲氧基苯基)吡啶
製備2-氯-6-(3-甲氧基苯基)吡啶(3.5g，16mmol)、二苯并噻吩-4-酸(4g，17.5mmol)、磷酸鉀(10.2g，48mmol)、二甲氧基乙烷(500mL)及水(50mL)之混合物。將氮氣直接鼓入混合物中15分鐘。接著添加參(二亞苄基丙酮)二鈀(147mg，0.16mmol)及2-二環己基膦基-2',6'-二甲氧基聯苯(263mg，0.64mmol)，且接著將氮氣鼓入混合物中另15分鐘。在氮氣下將反應混合物加熱至回流隔夜。次日，將反應混合物冷卻至室溫。將有機層分離且將水層用二氯甲烷萃取。將所組合之有機層經硫酸鎂乾燥，過濾且蒸發。將混合物藉由二氧化矽管柱(使用己烷中之至多10%乙酸乙酯)純化，得到3.8g黃色固體(65%)。
3.合成3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯酚
將2-(二苯并[b,d]噻吩-4-基)-6-(3-甲氧基苯基)吡啶(3.8g，10.3mmol)溶於120mL二氯甲烷中。在氮氣下，將溶液冷卻至0℃。在0℃下，緩慢添加BBr3(22.8mL，1M，於己烷中)，且接著緩慢升至室溫。將混合物在室溫下攪拌隔夜。觀測到褐色固體形成。藉由添加100mL水緩慢中止反應。藉由旋轉蒸發移除二氯甲烷。接著將混合物回流三小時。添加飽和碳酸氫鈉溶液以中和混合物，藉由二氯甲烷及乙酸乙酯萃取。將所組合之有機層經硫酸鎂乾燥，過濾且在減壓下濃縮，獲得4克暗褐色玻璃狀固體。該產物無需進一步純化便可用於下一步驟。
4.合成3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯基三氟甲磺酸酯
將3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯酚(4g，11.3mmol)懸浮於100mL吡啶中，用丙酮/冰浴冷卻至-10℃。在氮氣下緩慢添加三氟甲磺酸酐(2.29mL，13.6mmol)。將混合物在0℃下攪拌兩小時，接著傾注於飽和碳酸氫鈉溶液(200mL)中。藉由乙酸乙酯萃取混合物。將所組合之有機層經硫酸鎂乾燥，過濾且蒸發。將混合物藉由二氧化矽管柱(使用己烷中之至多15%乙酸乙酯)純化兩次。接著藉由添加己烷使產物自其二氯甲烷溶液中沈澱，得到1.8克白色固體(最後兩個步驟之組合產率為36%)。
5.合成化合物21S
製備3-(6-(二苯并[b,d]噻吩-4-基)吡啶-2-基)苯基三氟甲磺酸酯(1.65g，3.4mmol)、4,4,5,5-四甲基-2-(聯伸三苯-2-基)-1,3,2-二氧硼戊烷(1.32g，3.7mmol)、磷酸鉀(2.16g，10.2mmol)、甲苯(100mL)及水(10mL)之混合物。將氮氣直接鼓入混合物中25分鐘。接著添加參(二亞苄基丙酮)二鈀(31mg，0.034mmol)及2-二環己基膦基-2',6'-二甲氧基聯苯(55mg，0.14mmol)，且接著將氮氣鼓入混合物中另15分鐘。在氮氣下，將反應混合物加熱至回流歷時8小時。次日，將反應混合物冷卻至室溫。藉由過濾收集殘餘物，藉由甲苯、二氯甲烷及甲醇過量洗滌，得到1.8克灰色固體，在260℃下昇華兩次後，用於裝置製造。
實例10 化合物4S
1.合成2,11-雙(3-甲氧基苯基)聯伸三苯
製備聯伸三苯-2,11-二基雙(三氟甲磺酸酯)(2g，3.8mmol)、3-甲氧基苯基酸(2.3g，15mmol)、磷酸三鉀(4.8g，23mmol)、甲苯(100mL)及水(10mL)之混合物。將氮氣直接鼓入混合物中30分鐘。接著，添加參(二亞苄基丙酮)二鈀(70mg，0.076mmol)及雙(環己基)- 2-二苯基膦(125mg，0.30mmol)，且接著將氮氣鼓入混合物中另15分鐘。在氮氣下將反應物回流3小時。冷卻至室溫之後，收集反應混合物之有機層，經硫酸鎂乾燥，且在減壓下濃縮。將粗產物藉由二氧化矽凝膠急驟層析法純化，得到1.6g白色固體(產率95%)。
2.合成3,3'-(聯伸三苯-2,11-二基)二苯酚
在氮氣下，將2,11-雙(3-甲氧基苯基)聯伸三苯(1.6g，3.7mmol)與鹽酸吡啶(4.3g，37mmol)之混合物加熱至220℃歷時兩個半小時。將反應物冷卻至室溫，且用水洗滌。藉由過濾收集1.6g褐色殘餘物，在真空下乾燥且無需進一步純化便可用於下一步驟。
3.合成3,3'-(聯伸三苯-2,11-二基)雙(3,1-伸苯基)雙(三氟甲磺酸酯)
將3,3'-(聯伸三苯-2,11-二基)二苯酚(1.6g，3.9mmol)懸浮於50mL二氯甲烷與5mL吡啶之混合物中。將混合物藉由冰/水浴冷卻至0℃。將三氟甲磺酸酐(1.44mL，8.5mmol)溶於30mL二氯甲烷中且在氮氣下、在0℃下、緩慢添加入反應混合物中。接著，在氮氣下、在室溫下將反應物攪拌隔夜。將20mL甲醇添加至反應物中。藉由旋轉蒸發將混合物濃縮。將殘餘物懸浮於水中，接著藉由過濾收集。用水 洗滌之後，將殘餘物在真空下乾燥。將粗產物藉由二氧化矽急驟層析法(使用己烷中之至多30%二氯甲烷)純化，得到1.6克白色固體(最後兩個步驟之組合產率：65%)。
4.合成化合物4S
製備3,3'-(聯伸三苯-2,11-二基)雙(3,1-伸苯基)雙(三氟甲磺酸酯)(1.6g，2.4mmol)、二苯并噻吩-4-酸(2.7g，12mmol)、磷酸三鉀(3.4mmol，16mmol)、甲苯(100mL)與水(50mL)之混合物。將氮氣直接鼓入混合物中1小時。接著，添加參(二亞苄基丙酮)二鈀(44mg，0.048mmol)及雙(環己基)-2-二苯基膦(78mg，0.19mmol)，且接著將氮氣鼓入混合物中另30分鐘。將反應物回流隔夜。將反應物冷卻至室溫之後，藉由過濾收集殘餘物且藉由甲醇及二氯甲烷洗滌以得到最終產物。
實例11 化合物23S
1.合成4-苯基二苯并噻吩
將10g(41.6mmol)4-二苯并噻吩酸、6.25g(39.6mmol)溴苯、366mg(0.39mmol)Pd2(dba)3、656mg(1.6mmol)S-phose、25.4g(120mmol)K3PO4、180mL甲苯及20mL水饋入500mL燒瓶中。將混合物在氮氣下加熱至回流隔夜。將反應混合物藉由二氧化矽凝膠柱 層析法(使用純己烷作為溶離劑)純化。獲得約8.5g(83%)白色固體產物，產物藉由MS確認。
2.合成4-苯基二苯并噻吩-6- 酸
在250mL三頸燒瓶中，將3.5g(13.4mmol)4-苯基二苯并噻吩溶於約30mL無水THF中且冷卻至-78℃。向混合物中添加17mL(27mmol)1.6M BuLi(於己烷中)且攪拌30分鐘。移除冷卻浴且將反應物攪拌隔夜。再次將反應混合物冷卻至-78℃且添加4.5mL(40mmol)硼酸三甲酯且在室溫下攪拌4小時。添加約100 1M HCl且持續攪拌1小時。藉由乙酸乙酯萃取混合物且將有機萃取物組合。將溶劑蒸乾。將固體添加至約100mL於己烷中之20%乙酸乙酯中，攪拌數小時且接著過濾。將經過濾之固體藉由己烷洗滌數次。獲得約2.5g白色固體產物，產物藉由質子NMR確認。
3.合成化合物23S
將2.4g(7.89mmol)上述酸、3.3g(7.2mmol)3-(聯伸三苯-2-基)苯基三氟甲磺酸酯、67mg(0.08mmol)Pd2(dba)3、120mg(0.3mmol)S-phose、4.6g(21.7mmol)K3PO4、90mL甲苯及10mL水饋入250mL燒瓶中。在氮氣下，將混合物加熱至回流歷時6.5小時。將反 應混合物用分離漏斗分離且將有機相藉由二氧化矽凝膠柱層析法(使用己烷中之20%二氯甲烷作為溶離劑)及自甲苯及己烷混合物中再結晶來純化。獲得約3.8g(94%)白色固體產物，產物藉由質子NMR確認。
實例12 化合物24S
1.合成2,8-二苯基苯并噻吩
將7.0g(20.4mmol)2,8-二溴二苯并噻吩、6.4g(51.1mmol)苯基酸、187mg(0.2mmol)Pd2(dba)3、335mg(0.8mmol)S-phose、13g(61.2mmol)K3PO4、90mL甲苯及10mL水饋入250mL燒瓶中。在氮氣下，將混合物加熱至回流歷時4小時。將反應混合物用分離漏斗分離且將有機相藉由二氧化矽凝膠柱層析法(使用己烷中之20%二氯甲烷作為溶離劑)純化。獲得約6.6g(96%)白色固體產物，產物藉由GC-MS確認。
2.合成2,8-二苯基二苯并噻吩-4- 酸
在250mL三頸燒瓶中，將3.8g(11.3mmol)2,8-二苯基苯并噻吩 溶於約30mL無水THF中。在氮氣下，在-78℃下，向混合物中添加約18mL(28.3mmol)1.6M BuLi(於己烷中)。將混合物溫至室溫且持續攪拌18小時。再次將反應混合物冷卻至-78℃且添加3.8mL(34mmol)硼酸三甲酯且在室溫下將混合物持續攪拌4小時，接著添加約60mL 1M HCl，攪拌1小時。藉由乙酸乙酯萃取混合物，且將有機相組合。將溶劑蒸乾。將固體添加至約100mL於己烷中之20%乙酸乙酯中。攪拌數小時且接著過濾。將經過濾之固體用己烷洗滌3次。獲得2g白色固體產物，產物藉由質子NMR確認。
3.合成化合物24S
將2.0g(5.26mmol)2,8-二苯基二苯并噻吩-4-酸、2.18g(4.78mmol)3-(聯伸三苯-2-基)苯基三氟甲磺酸酯、45mg(0.05mmol)Pd2(dba)3、80mg(0.19mmol)S-phose、3.2g(14mmol)K3PO4、90mL甲苯及10mL水饋入250mL燒瓶中。將混合物在氮氣下加熱至回流隔夜。將反應混合物用分離漏斗分離且將有機相藉由二氧化矽凝膠柱層析法(使用己烷中之20%二氯甲烷作為溶離劑)及自甲苯及己烷混合物中再結晶來純化。獲得約2.52g(84%)白色固體產物，產物藉由質子NMR確認。
實例13 化合物25S
1.合成2,8-二苯基苯并噻吩
將7.0g(20.4mmol)2,8-二溴二苯并噻吩、6.4g(51.1mmol)苯基酸、187mg(0.2mmol)Pd2(dba)3、335mg(0.8mmol)S-phose、13g(61.2mmol)K3PO4、90mL甲苯及10mL水饋入250mL燒瓶中。在氮氣下，將混合物加熱至回流歷時4小時。將反應混合物用分離漏斗分離且將有機相藉由二氧化矽凝膠柱層析法(使用己烷中之20%二氯甲烷作為溶離劑)純化。獲得約6.6g(96%)白色固體產物，產物藉由GC-MS確認。
2.合成2,8-二苯基二苯并噻吩-4- 酸
[UDC請核實對上述中間物所指定之名稱]
在250mL三頸燒瓶中，將3.8g(11.3mmol)2,8-二苯基苯并噻吩溶於約30mL無水THF中。在氮氣下，在-78℃下，向混合物中添加約18mL(28.3mmol)1.6M BuLi(於己烷中)。將混合物溫至室溫且持續攪拌18小時。再次將反應混合物冷卻至-78℃，且添加3.8mL(34mmol)硼酸三甲酯，且將混合物在室溫下持續攪拌4小時。接著添加約60mL 1M HCl，連續攪拌1小時。藉由乙酸乙酯萃取混合物，且將有機相組合。將溶劑蒸乾。將固體添加至約100mL於己烷中之20%乙酸乙酯中，攪拌數小時且接著過濾。將經過濾之固體用己烷洗滌。獲得約2.2g白色固體產物，產物藉由質子NMR確認。
3.合成2,4,8-三苯基苯并噻吩
將5.5g(14.5mmol)2,8-二苯基二苯并噻吩-4-酸、2.3g(14.5mmol)溴苯、135mg(0.15mmol)Pd2(dba)3、238mg(0.58mmol)S-phose、9.2g(43.2mmol)K3PO4、180mL甲苯及20mL水饋入500mL燒瓶中。將混合物在氮氣下加熱至回流隔夜。將反應混合物用分離漏斗分離且將有機相藉由二氧化矽凝膠柱層析法(使用己烷中之20%乙酸乙酯作為溶離劑)純化。獲得約5.1g之2,4,8-三苯基苯并噻吩白色固體產物，產物藉由質子NMR確認。
4.合成2,4,8-三苯基二苯并噻吩-6- 酸
將5.0g(12.13mmol)2,4,8-三苯基苯并噻吩溶於250mL三頸燒瓶中之約100mL無水THF中。在氮氣下，在-78℃下，向混合物中添加約19mL(30.3mmol)1.6M BuLi(於己烷中)。將混合物溫至室溫且持續攪拌18小時。再次將反應混合物冷卻至-78℃且添加3.8mL(34mmol)硼酸三甲酯且將混合物在室溫下持續攪拌4小時，接著添加約100mL 1M HCl，攪拌1.5小時。藉由乙酸乙酯萃取混合物，且將有機相組合。將溶劑蒸乾。將固體添加至約150mL於己烷中之20%乙酸 乙酯中。將混合物攪拌數小時且接著過濾。將經過濾之固體用己烷洗滌3次。獲得約4.5g白色固體產物，產物藉由質子NMR確認。
5.合成化合物25S
將3.5g(7.67mmol)2,4,8-三苯基二苯并噻吩-6-酸、3.2g(6.98mmol)3-(聯伸三苯-2-基)苯基三氟甲磺酸酯、64mg(0.077mmol)Pd2(dba)3、115mg(0.30mmol)S-phose、4.5g(22mmol)K3PO4、90mL甲苯及10mL水饋入250mL燒瓶中。將混合物在氮氣下加熱至回流隔夜。將反應混合物用分離漏斗分離且將有機相藉由二氧化矽凝膠柱層析法(使用己烷中之25%二氯甲烷作為溶離劑)及自甲苯及己烷混合物中再結晶來純化。獲得約4.5g(92%)白色固體產物，產物藉由質子NMR確認。
實例14 化合物2O
將3.9g(18.4mmol)二苯并呋喃-4-酸、7.0g(15.4mmol)3-(聯伸三苯-2-基)苯基三氟甲磺酸酯、141mg(0.154mmol)Pd2(dba)3、252 mg(0.46mmol)S-phose、9.8g(46mmol)K3PO4、180mL甲苯及20mL水饋入500mL燒瓶中。將混合物在氮氣下加熱至回流隔夜。將反應混合物用分離漏斗分離且將有機相藉由二氧化矽凝膠柱層析法(使用己烷中之20%二氯甲烷作為溶離劑)純化。獲得約6.2g(87%)白色固體產物，產物藉由質子NMR確認。
裝置實例
所有實例裝置皆藉由高真空(<10-7托(Torr))熱蒸發法製造。陽極電極為約800Å或1200Å之氧化銦錫(ITO)。陰極由10Å之LiF、繼之1,000Å之Al組成。所有裝置在製造之後立即在氮氣手套箱(H2O與O2<1ppm)中用密封有環氧樹脂的玻璃蓋封裝，且將吸濕劑併入封裝內。
表1及2中之裝置實例1-30之有機堆疊由以下各者依序組成：ITO表面；100Å之化合物A作為電洞注入層(HIL)；300Å之4,4'-雙[N-(1-萘基)-N-苯基胺基]聯苯(α-NPD)作為電洞傳遞層(HTL)；300Å之摻有10wt%或15wt% Ir磷光化合物之本發明化合物作為發光層(EML)；50Å或100Å之HPT或本發明化合物作為ETL2；及400Å或450Å之Alq3(參-8-羥基喹啉鋁)作為ETL1。
比較實例1及2之製造類似於裝置實例，例外之處為CBP作為主體。
裝置結構及數據總結於表1至5中。表1展示裝置結構且表2展示彼等裝置之對應量測結果，而表3至5各展示裝置結構與所測實驗結果。如本文中所使用，化合物A、化合物B、NPD及HPT具有以下結構：
由裝置實例1-30可見，化合物1S、2S、20S、9S、23S、24S及2O在綠色磷光OLED中作為主體可得到高裝置效率(在1000cd/m2時，LE>40cd/A)，說明聯伸三苯與苯并噻吩組合(直接連接或間伸苯基連接)對於有效綠色電致磷光發光具有足夠高的三重態能量。
顯然，將化合物1S、2S、21S、23S及2O作為主體併入的裝置具有高穩定性。裝置實例1與比較實例2僅主體不同。裝置實例1使用化合物1作為主體，而比較實例2使用常用主體CBP。壽命期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%所需的時間)分別為270小時及105小時，裝置實例1具有稍微更高之L0。此說明裝置穩定性幾乎改良3倍。類似地，使用化合物2S作為主體的裝置實例5穩定性比比較實例2至少大2.5倍。使用化合物2S作為主體的裝置實例9比使用CBP作為主體的比較實例1穩定性大至少3倍。亦顯然，該等化合物可很好地起增強層材料(ETL2)之作用。裝置實例10與裝置實例9皆以化合物2S作為主體，但分別以化合物2及HPT作為增強層。裝置實例10與裝置實例9分別具有450小時及380小時之T0.8，說明化合物2S作為增強層材料之良好效能。裝置實例21具有620小時之T0.8，此大大高於具有CBP之比較實例1或2裝置之壽 命期。
此數據說明，含有聯伸三苯的苯并噻吩(尤其含有聯伸三苯的二苯并噻吩)為磷光OLED之優良主體及增強層材料，與常用作主體的CBP相比，可提供至少相同之效率及穩定性之多倍改良。含有聯伸三苯之苯并噻吩之更多共軛型式(例如經由對伸苯基(諸如4,4'-聯苯)連接的聯伸三苯與苯并噻吩單元)非常適於能量更低(黃色至紅色)的磷光OLED。
表3展示具有發光層之某些裝置之裝置結構及實驗量測結果，該發光層具有介於第一有機層與第二有機層(其中兩層中之主體與摻雜劑(亦即非發光材料)為相同材料且兩層中之磷光材料為相同材料，但濃度不同)之間的介面。表3中之所有裝置具有化合物A之100Å電洞注入層；視特定裝置而定之不同材料之100Å增強層(ETL2)；400Å電子傳遞層(ETL1)；及LiF/Al陰極。發光層包括第一有機層與第二有機層(之間具有一介面)，其中第一有機層為300Å之非發光材料(表3中之"主體")(濃度為70wt%)與磷光材料(表3中之"摻雜劑")(濃度為30wt%)，第二有機層為300Å之相同非發光材料(表3中之"主體")(但濃度為90wt%)與相同磷光材料(表3中之"摻雜劑")(但濃度為10wt%)。各裝置之特定主體及摻雜劑標明於表3中。因此，表3之裝置之一般裝置結構為：ITO(1200Å)/化合物A(100Å)/主體(70wt%)：摻雜劑(30wt%)(300Å)/主體(90wt%)：摻雜劑(10wt%)(300Å)/ETL2(100Å)/Alq3(400Å)/LiF/Al。
表3中之裝置(使用化合物2S作為主體且使用化合物2S或HPT作為增強層材料)展示高效率(在1000cd/m2下，>46cd/A)。更顯著的為1000小時(裝置實例A、B及D)或甚至2000小時(裝置實例C)之LT80%之穩定性，使得該等裝置成為迄今為止壽命期最長的綠色磷光OLED。
具有聯伸三苯-苯并噻吩組合之裝置之良好效能及高穩定性據信可歸因於聯伸三苯與苯并噻吩電荷傳遞單元所提供之良好電荷平衡，及苯并噻吩與聯伸三苯單元所提供之π-共軛對分子之氧化態/還原態的穩定化作用。
表4及表5展示具有發光層之裝置之裝置結構及實驗量測結果，該發光層含有與中心吡啶連接的聯伸三苯及苯并稠合噻吩。
表4中之所有裝置具有化合物A之100Å電洞注入層；NPD之300Å電洞傳遞層；以化合物21S作為主體及化合物A作為摻雜劑的300Å發光層；具有表4中所標明之材料及厚度的障壁層(BL)；具有表4中所標明之厚度之Alq電子傳遞層(ETL)；及LiF/Al陰極。特定而言，BL厚度與ETL厚度合計500Å。發光層為包括主體及摻雜劑的單層。各裝置之摻雜劑之特定百分比標明於表4中。因此，表4之一般裝置結構為：ITO(1200Å)/化合物A(100Å)/NPD(300Å)/化合物21S：化合物A x%(300Å)/BL/Alq(500Å-BL)/LiF(10)/Al(1000)。
表5之所有裝置具有化合物A之100Å電洞注入層；具有表5中所標明之材料的300Å電洞傳遞層；以化合物22S作為主體及化合物A作為摻雜劑的300Å發光層；具有表5中所標明之材料及厚度的障壁層(BL)；厚度等於500Å減去障壁層(BL)厚度(Å)的電子傳遞層；及LiF/Al陰極。特定而言，BL厚度與ETL厚度合計500Å。發光層為包括主體及摻雜劑的單層。各裝置之特定百分比標明於表5中。因此，表5之一般裝置結構為：ITO(1200Å)/化合物A(100Å)/HTL(300Å)/化合物22S：化合物A x%(300Å)/BL/Alq(500Å-BL)/LiF(10)/Al(1000)。
應瞭解，本文中所述的不同實施例僅視為實例，且不希望限制本發明之範圍。舉例而言，在不背離本發明之精神的情況下，本文中所述的很多物質及結構可經其他物質及結構取代。因此，如熟習此項技術者所顯而易見，所主張之本發明包括本文中所述之特定實例及較佳實施例之變化形式。特定而言，含有聯伸三苯的基團可與任何位置之苯并噻吩或苯并呋喃連接。應瞭解本發明運作原理不希望受到各種理論限制。

Claims (21)

  1. 一種化合物，其係選自由以下結構所組成之群： 其中R1、R2、R3、R4、R5、R6、R7、R8、及R9表示單取代、二取代、三取代、四取代或無取代；及其中R1、R2、R3、R4、R5、R6、R7、R8及R9為獨立選自由以下各基組成之群的非稠合取代基：氫、CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2及CnH2n-Ar1，其中n為1、2、3、4、5、6、7、8、9或10，且Ar1及Ar2獨立地選自由苯、聯苯、萘、聯伸三苯及咔唑所組成之群。
  2. 如請求項1之化合物，其中該化合物係選自由以下各者所組成之群：
  3. 如請求項1之化合物，其具有結構為：
  4. 如請求項1之化合物，其具有結構為：
  5. 如請求項1之化合物，其具有結構為：
  6. 如請求項1之化合物，其具有結構為：
  7. 如請求項1之化合物，其具有結構為：
  8. 如請求項1之化合物，其具有結構為：
  9. 如請求項1之化合物，其具有結構為：
  10. 如請求項1之化合物，其具有結構為：
  11. 如請求項1之化合物，其具有結構為：
  12. 如請求項1之化合物，其具有結構為：
  13. 如請求項1之化合物，其具有結構為：
  14. 如請求項1之化合物，其具有結構為：
  15. 如請求項1之化合物，其具有結構為：
  16. 一種有機發光裝置，其包含：一陽極；一陰極；及一配置於該陽極與該陰極之間的有機層，其中該有機層包含選自由以下結構所組成之群所表示的化合物： 其中R1、R2、R3、R4、R5、R6、R7、R8、及R9表示單取代、二取代、三取代、四取代或無取代；及其中R1、R2、R3、R4、R5、R6、R7、R8及R9為獨立選自由以下各基組成之群的非稠合取代基：氫、CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2及CnH2n-Ar1，其中n為1、2、3、4、5、6、7、8、9或10，且Ar1及Ar2獨立地選自由苯、聯苯、萘、聯伸三苯及咔唑所組成之群。
  17. 如請求項16之裝置，其中該有機層為發光層。
  18. 如請求項17之裝置，其中該有機層進一步包括磷光發光物。
  19. 如請求項18之裝置，其中該磷光發光物為銥錯合物。
  20. 如請求項16之裝置，其中該有機層包含化合物2S，及銥錯合物。
  21. 如請求項16之裝置，其中芳基獨立地選自由苯、聯苯、萘、聯伸三苯及咔唑所組成之群。
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