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TWI418607B - A compound for an organic electric field light emitting element, and an organic electric field light emitting element - Google Patents

A compound for an organic electric field light emitting element, and an organic electric field light emitting element Download PDF

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TWI418607B
TWI418607B TW096142493A TW96142493A TWI418607B TW I418607 B TWI418607 B TW I418607B TW 096142493 A TW096142493 A TW 096142493A TW 96142493 A TW96142493 A TW 96142493A TW I418607 B TWI418607 B TW I418607B
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Takahiro Kai
Masaki Komori
Toshihiro Yamamoto
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Nippon Steel & Sumikin Chem Co
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Description

有機電場發光元件用化合物及有機電場發光元件
本發明係關於一種新的有機電場發光元件用化合物及有機電場發光元件(以下稱為有機EL元件)，更詳細地係關於藉由併用磷光發光摻雜物及具有特定構造的主體化合物而顯示高亮度之有機EL元件。
一般有機EL元件，其最簡單之構造係由發光層及夾住該層的一對對向電極所構成。亦即，有機EL元件係利用兩電極間施加電場時，使電子從陰極注入，使電洞從陽極注入，這些於發光層之再結合能階從導電帶回到價電子帶時，能量以光放出之現象。
近年，進行使用有機薄膜之EL元件的開發。特別為了提高發光效率，以提高載子從電極注入之效率為目的，進行電極種類的最佳化，藉由將由芳香族二胺所構成的電洞傳輸層與由8-羥基喹啉鋁錯合物(以下稱為Alq3)所構成的發光層，以薄膜設置於電極之間之元件的開發，與傳統使用蔥等的單結晶之元件比較，由於可大幅地改善發光效率，朝具有所謂自發光‧高速應答性的特徵之高性能平面面板的實用為目標進展。
而且，嘗試提高元件的發光效率，也檢討使用磷光而非螢光。以設置上述由芳香族二胺所構成的電洞傳輸層與由Alq3所構成的發光層之元件為代表的多數元件係利用 螢光發光，若使用磷光發光，亦即利用三重態激發狀態的發光，與傳統使用螢光(單重態)的元件比較，被期待效率提高3倍的程度。為了該目的，雖檢討以香豆素(coumarin)衍生物、二苯基酮衍生物作為發光層，但只得到極低的亮度。然後，嘗試利用三重態，雖檢討使用銪錯合物，但也無法達到高效率的發光。
[專利文獻1]特表2003-515897號公報 [專利文獻2]特開2001-313178號公報 [專利文獻3]特開2002-305083號公報 [專利文獻4]特開2002-352957號公報 [專利文獻5]特開平11-162650號公報 [專利文獻6]特開平11-176578號公報
作為於有機EL元件的發光層所使用的磷光摻雜物，已於專利文獻1等揭露。作為代表者為三(2-苯基吡啶)銥錯合物(以下稱為Ir (ppy)3 )。
提案作為於有機EL元件的發光層所使用的主體材料，有於專利文獻2所介紹之咔唑化合物的CBP。綠色磷光發光材料Ir (ppy)3 的主體材料使用CBP時，CBP有電洞容易流動而電子流動困難的特性，破壞電荷注入的平衡，過剩的電洞流出至電子傳輸層側，結果從Ir (ppy)3 的發光效率低。
作為上述的解決手段，例如專利文獻3，於發光層與電子傳輸層之間設置電洞阻隔層之手段。藉由該電洞阻隔層，使電洞有效地累積於發光層中，可提高發光層中與電 子的再結合機率，而達成發光的高效率化。現在一般所使用的電洞阻隔層材料，例如2,9-二甲基-4,7-二苯基-1,10-菲繞啉(phenanthroline)(以下稱為BCP)以及雙(2-甲基-8-喹啉-N1,08)對-聯苯氧基鋁(以下稱為BAlq)。藉此可防止電子與電洞在電子傳輸層的再結合，但BCP係為即使於室溫也容易結晶化的材料，缺乏信賴性，元件的壽命極短。此外，雖有報告指出BAlq的Tg約為100℃時，有較好的元件壽命結果，但其電洞阻隔能力不足，從Ir (ppy)3 的發光效率低。
另一方面，專利文獻4所介紹之3-苯基-4-(1'-萘基)-5-苯基-1,2,4-三唑(以下稱為TAZ)雖被提案作為磷光有機EL元件的主體材料，其電子容易流動而電洞流動困難的特性，發光區域變成在電洞傳輸層側。因而，根據電洞傳輸層的材料，認為因與Ir (ppy)3 的相容性的問題，而從Ir (ppy)3 的發光效率低。例如作為電洞傳輸層，使用從高性能、高信賴性、高壽命的點最好之4,4'-雙(N-(1-萘基)-N-苯基胺基)聯苯(以下稱為NPB)，與Ir (ppy)3 的相容性差，引起從Ir (ppy)3 能量轉移至NPB，有發光效率低的問題。
而且，專利文獻5及6所揭露之吲哚咔唑(indolocarbazole)化合物，被推薦使用作為電洞傳輸材料，化合物的安定性雖被稱讚，但沒有教導使用作為磷光主體材料。而且，化合物的構造也與本發明的化合物不同。
有機EL元件為了應用於平面面板‧顯示器等的顯示元件，改善元件的發光效率的同時，必須充分確保驅動時的安定性。本發明有鑑於現狀，以提供具有高效率及高驅動安定性之實用上有用的有機EL元件及適合其之化合物為目的。
本發明人等專心檢討的結果，發現於有機EL元件使用特定構造的化合物，可解決上述課題，因而完成本發明。
亦即，本發明係藉由使用特定吲哚咔唑骨架之化合物，提供具有高效率及高驅動安定性之實用上有用的有機EL元件者。
本發明的有機電場發光元件用化合物，係以下述一般式(1)所表示。
〔化1〕
此處，環A表示與鄰接環在任意位置進行縮合之式(1a)所表示的雜環，X表示N或CH，X中至少之一為氮原子。Ar1 ~Ar3 表示獨立之非縮環構造的取代或未取代之芳香族烴基或芳香族雜環基，Ar2 或Ar3 可與含有X的環形成縮合環。R為氫或1價取代基。
於一般式(1)所表示的有機電場發光元件用化合物，係下述一般式(2)或(3)所表示的化合物。
一般式(2)及(3)中，X及Ar1 ~Ar3 與一般式(1)的意義相同。
而且，本發明係具有含上述的有機電場發光元件用化合物之有機層的有機電場發光元件。有利地，有機電場發光元件係於基板上所層合的陽極與陰極之間具有發光層之有機電場發光元件，其特徵為該發光層含有磷光發光性摻雜物及上述一般式(1)、(2)或(3)所表示的有機電場發光元件用化合物作為主體材料。
以下，詳細說明本發明的實施形態。
本發明的有機EL元件用化合物係以上述一般式(1)表示。一般式(1)所表示的化合物，具有咔唑環與吲哚環縮合之吲哚咔唑骨架。然後，具有含3個X的環(稱為含X環)與咔唑環的N結合，於各環結合R或Ar1 ~Ar3 的構造。而且，吲哚環係環A與苯環的縮合環。
式中，環A為與鄰接環縮合之式(1a)所表示的雜環。此處，式(1a)所表示的雜環，可在鄰接的咔唑環之任 意位置進行縮合。具體地，可在咔唑環的2,3-位、3,4-位或4,5-位的位置進行縮合。
於與咔唑環的N結合之含X環，X表示CH或N，X中至少之一為氮原子。較理想為1、2或3個X為氮原子。
Ar1 ~Ar3 表示非縮環構造的取代或未取代之芳香族烴基或非縮環構造的取代或未取代之芳香族雜環基。較理想的未取代之芳香族烴基，例如苯基、聯苯基、三苯基、四苯基等。較理想的未取代之芳香族雜環基，例如吡啶基(pyridyl)、嘧啶基(pyrimidyl)、三嗪基(triazyl)、咪唑基(imidazolyl)、噻吩基(thienyl)等。
於這些芳香族烴基或芳香族雜環基具有取代基的情況，作為較理想的取代基，例如C1 ~C4 的烷基、C1 ~C4 的烷氧基、苯氧基、烷硫基、取代的胺基、乙醯基等。此外，例如碳數5~18的芳香族烴基以及碳數3~17的芳香族雜環基等。
而且，Ar2 或Ar3 可與含X環縮合而形成縮合環。
於與咔唑環的N結合之含X環，該環為吡啶環時，一般式(1)中，對於與咔唑環的N結合的碳而言p-位的X為氮較理想，於嘧啶環的情況，o-位的2個X為氮較理想。
R表示氫或1價的取代基。R為獨立之烷基、芳烷基、烯基、炔基、氰基、二烷基胺基、二芳基胺基、二芳烷基胺基、胺基、硝基、醯基、烷氧基羰基、羧基、烷氧基 、烷基磺醯基、鹵烷基、羥基、醯胺基、取代或未取代的芳香族烴基或芳香族雜環基。較理想的1價的取代基，例如C1 ~C4 的烷基、C1 ~C4 的烷氧基、苯氧基、烷硫基、取代的胺基、乙醯基等。再者，例如取代或未取代的碳數5~18的芳香族烴基或碳數3~17的芳香族雜環基較理想。
上述一般式(1)所表示的化合物中，作為較理想的化合物為上述一般式(2)及(3)所表示的化合物。然後，一般式(2)及(3)之X、Ar1 ~Ar3 及R，與一般式(1)式中的X、Ar1 ~Ar3 及R對應，意義相同。較理想的X、Ar1 ~Ar3 及R，也與上述相同。而且，所謂意義相同，係指這些記號的定義相同，這些記號有複數個存在的情況下，在上述的定義範圍內，可互相變化。
本發明的有機EL元件用化合物，可以習知的方法容易地製造。例如上述一般式(2)所表示的化合物，參考Synlett, 2005, No. 1. p42-48所表示的合成例，可藉由以下的反應式製造。
而且，一般式(3)可參考Arcbiv der Pharmazie(Weinheim,德國),1987, 320 (3), p280-2所表示的合成例，可藉由以下的反應式製造。下式中，L與Ar1 ~Ar3 具有相同的意義。
一般式(1)或(2)、(3)所表示的化合物之較理想的具體例，如以下所示，但不限於這些例子。
藉由使本發明的有機電場發光元件用化合物含於有機EL元件的有機層，可賦予優異的有機電場發光元件。有利地可使其含於選自發光層、電洞傳輸層、電子傳輸層及電洞阻隔元件層中至少一有機層。更理想地，可使其含於含有磷光發光摻雜物的發光層，作為主體材料。
本發明的有機電場發光元件，係於基板上所層合的陽極與陰極之間具有發光層之有機電場發光元件，該發光層含有磷光發光性摻雜物及上述的有機EL元件用化合物作為主體材料。有機EL元件的構造，只要是具有基板、陽極、陰極及發光層者即可，於陽極與發光層之間，具有電洞注入傳輸層以及於陰極與發光層之間具有電子注入傳輸層較理想。再者，於發光層與電子注入傳輸層之間具有電 洞阻隔層較理想。
作為發光層中磷光發光摻雜物材料，具有含有選自釕、銠、鈀、銀、錸、鋨、銥、鉑及金中至少之一金屬之有機金屬錯合物。如此的有機金屬錯合物，在前述專利文獻等為習知者，可從這些之中選擇使用。
作為較理想的磷光發光摻雜物，例如以Ir等貴重金屬為中心金屬之Ir (ppy)3 等錯合物類、Ir (bt)2．acac3等錯合物類、PtOEt3等錯合物類。這些錯合物類的具體例如以下所示，但不限於下述的化合物。
前述磷光發光摻雜物含於發光層中的量，以5~10重量%的範圍較理想。
然後，一邊參照圖面，說明本發明的有機EL元件的構造，但本發明的有機EL元件的構造不限於任何圖示。
圖1為表示本發明所使用的一般有機EL元件的構造 例之模型剖面圖，1表示基板，2表示陽極，3表示電洞注入層，4表示電洞傳輸層，5表示發光層，6表示電子傳輸層，7表示陰極。於本發明的有機EL元件，具有基板、陽極、發光層及陰極作為必須的層，於必須的層以外的層以外，可具有電洞注入傳輸層、電子注入傳輸層，再者於發光層與電子注入傳輸層之間，可具有電洞阻隔層。而且，電洞注入傳輸層係指電洞注入層與電洞傳輸層中之一或兩者，電子注入傳輸層係指電子注入層與電子傳輸層中之一或兩者。
而且，與圖1相反的構造，亦即於基板1上，可依序層合陰極7、電子傳輸層6、發光層5、電洞傳輸層4、陽極2，如上述可於至少一側為透明性高的2片基板之間，設置本發明的有機EL元件。於該情況，也可依據需要而可追加或省略層。
本發明可適用有機EL元件為單一元件、配置成陣列狀的構造所構成的元件、陽極與陰極配置成X-Y矩陣狀的構造的任一種。根據本發明的有機EL元件，藉由使發光層含有具有特定骨架之化合物及磷光發光摻雜物，可得比傳統使用由單重態發光之元件的發光效率高，且驅動安定性也大幅改善之元件，於全彩或多彩的面板之應用，可發揮優異的性能。
[實施例]
以下，藉由實施例，更詳細地說明本發明，但本發明 當然不限於這些實施例，只要不超過其主旨，可以各種形態實施。而且，化合物的編號係對應上述化學式所附的編號。
實施例1
於除氣、氮氣取代之2000毫升的3口燒瓶，加入1,2-環己二酮33.3g(297.0毫莫耳)、苯基聯胺鹽酸鹽86.0g(594.7毫莫耳)，於其中加入乙醇1000毫升，使其攪拌。然後，於同一燒瓶內，以5分鐘滴入濃硫酸3.0g(30.6毫莫耳)。然後加熱至65℃，攪拌4小時。冷卻至室溫後，過濾所產生的紫茶色結晶後，將過濾的結晶以500毫升的乙醇進行2次的再成漿(reslurrying)洗淨。將其減壓乾燥，得到紫茶色粉末80.0g(280.5毫莫耳，產率96.3%)。
然後，於1000毫升的3口燒瓶，加入上述紫茶色粉末72.0g(261.5毫莫耳)，於其中加入乙酸720g、三氟乙酸72.0g，使其攪拌。然後加熱至100℃，攪拌15小時。冷卻至室溫後，過濾所產生的黃色結晶後，將過濾的結晶以200毫升的乙酸進行洗滌洗淨後，以己烷200毫升進行洗滌洗淨。將其減壓乾燥，得到白色粉末A' 30.0g(117.1毫莫耳，產率44.8%)。所得的白色粉末A'為吲哚[2,3-a]咔唑。
然後，於1000毫升的3口燒瓶，加入上述所得的白色粉末26.0g(101.4毫莫耳)、碘苯122.7g(601.4毫莫 耳)、碘化銅54.7g(287.2毫莫耳)、碳酸鉀66.7g(482.6毫莫耳)，於其中加入喹啉(quinoline)800毫升，使其攪拌。然後加熱至190℃，攪拌72小時。一旦冷卻至室溫後，加入水500毫升、二氯甲烷500毫升，進行攪拌後，過濾所生成的黃色結晶。將過濾液移至2000毫升的分液漏斗，分成有機層與水層。將有機層以500毫升的水進行3次洗淨，然後，將所得的有機層以硫酸鎂進行脫水，過濾硫酸鎂後，將溶劑減壓蒸餾除去。然後，以管柱層析法進行精製，得到白色固體A 13.7g(41.2毫莫耳，產率40.6%)。所得的白色粉末A為11-苯基吲哚[2,3-a]咔唑。
接著，於除氣、氮氣取代之200毫升的3口燒瓶，加入三聚氯化氰12.5g(0.068莫耳)、脫水THF55毫升，於冰浴中氮氣氣流下進行攪拌。然後，於同一燒瓶內以2小時滴入32%溴化苯鎂的THF溶液105.6g(0.186莫耳)。滴入中的溫度保持於15℃以下。滴完後，持續攪拌1.5小時。然後，於同一燒瓶內加入甲苯80g。然後，於冰浴中進行冷卻，於同一燒瓶內以15分鐘滴入12%HClaq76.5g(0.254莫耳)。滴入中的溫度保持於30℃以下。將燒瓶的內容物移至500毫升的分液漏斗，分成有機層與水層。將有機層以100毫升的水進行3次洗淨，然後，將所得的有機層以硫酸鎂進行脫水，過濾硫酸鎂後，將溶劑減壓蒸餾除去，得到21.1g的粗製品。然後，加入甲醇110g，進行攪拌1小時後，過濾析出物，以真空乾燥機進行減壓 乾燥，得到白色固體B 14.5g(6.5毫莫耳，產率50.2%)。所得的白色固體B為2-氯-4,6-二苯基-1,3,5-三嗪(triazine)。
然後，於除氣、氮氣取代之2000毫升的3口燒瓶，加入55%氫氧化鈉2.18g(50.0毫莫耳)、脫水N,N'-二甲基甲醯胺70毫升，在氮氣氣流中進行攪拌。於上述所得的白色固體A 13.5g(40.6毫莫耳)中加入脫水N,N'-二甲基甲醯胺150毫升，使其溶解，然後於同一燒瓶內以10分鐘滴入。滴完後，持續攪拌1小時。然後，於上述所得的白色固體B 10.4g(39.0毫莫耳)中加入脫水N,N'-二甲基甲醯胺150毫升，使其溶解，然後於同一燒瓶內以1小時滴入。滴完後，持續攪拌3小時。然後，加入水600g，過濾所析出的結晶。將所過濾的結晶以水300g進行2次的再成漿，然後以甲醇300g進行再成漿，所得的結晶以真空乾燥機進行減壓乾燥，得到黃色結晶21.0g。
接著，於1000毫升的燒瓶，加入所得的黃色結晶21.0g、THF108.6g，使其溶解。於同一燒瓶內，滴入甲醇660g。過濾析出物，以真空乾燥機進行減壓乾燥，得到黃色固體(化合物3)12.7g(22.6毫莫耳、產率54.6%)。
化合物3的EI-MS (M+1)為563，熔點為263℃。
實施例2
於玻璃基板上，以真空蒸鍍法，在真空度4×10-4 Pa的條件，將化合物3從蒸鍍源進行蒸鍍，以0.1nm/秒形成厚 度50nm的薄膜。將所製作的薄膜以螢光測定裝置進行評價時，觀察到發光。
另外，於玻璃基板上，以真空蒸鍍法，在真空度4.0×10-4 Pa的條件，將化合物3與Ir (ppy)3 從不同的蒸鍍源進行蒸鍍，以0.1nm/秒形成厚度50nm的Ir (ppy)3 的濃度為7.0%之薄膜。所製作的該薄膜以螢光測定裝置進行評價，激發波長係使用化合物3的最大吸收波長，此時觀察所發出的光，與只有化合物3的薄膜時所發出的光比較。結果表示於表1。
比較例1
將薄膜的主體材料，以Alq3取代化合物3製作薄膜以外，與實施例2同樣地進行評價。結果表示於表1。
得知發光層的主體材料使用化合物3的情況下，能量轉移至Ir (ppy)3 ，觀察到從Ir (ppy)3 的發光，使用Alq3的情況下，能量沒有轉移至Ir (ppy)3 ，Alq3本身發出螢光。
實施例3
製作圖1中，省略電洞注入層，追加電子注入層之構 成的有機EL元件。於形成有膜厚150nm的ITO所構成的陽極之玻璃基板上，各薄膜以真空蒸鍍法，在真空度4.0×10-4 Pa下層合。首先，於ITO上形成60nm厚度的NPB，作為電洞傳輸層。
然後，於電洞傳輸層上，將作為發光層之化合物3與Ir (ppy)3 從不同的蒸鍍源進行共蒸鍍，形成25nm的厚度。此時，Ir (ppy)3 的濃度為7.0重量%。然後，形成50nm厚度的Alq3作為電子傳輸層。再於電子傳輸層上，形成0.5nm厚度的氟化鋰(LiF)作為電子注入層。最後於電子注入層上，形成170nm厚度的鋁(Al)作為電極，而製作完成有機EL元件。
於所得的有機EL元件，連接外部電源，施以直流電壓時，確認具有如表2所示的發光特性。於表2中，亮度、電壓及發光效率係表示在10mA/m2 的值。而且，元件發光光譜的最大波長為517nm，得知得到來自Ir (ppy)3 的發光。
比較例2
除使用HMTPD作為電洞傳輸層、TAZ作為發光層的主體材料以外，與實施例3同樣地製作有機EL元件。
比較例3
除使用TAZ作為發光層的主體材料以外，與實施例3同樣地製作有機EL元件。
實施例4
(化合物114的合成) 於除氣、氮氣取代之2000毫升的3口燒瓶，加入3,3'-亞甲基二吲哚(3,3'-methylenediindole)50.69g(0.2058莫耳)、原甲酸三乙酯(triethyl orthoformate)30.55g(0.2061莫耳)，於其中加入甲醇640g，使其攪拌。於其中，以3分鐘滴入濃硫酸5.0g(0.0515莫耳)後，進行1小時的加熱回流。冷卻至室溫後，過濾所生成的紅茶色結晶，將所得的結晶以甲醇500毫升，進行2次再成漿洗淨。減壓蒸餾除去溶劑，得到紅茶色粉末狀的固體C36.81g(0.1438莫耳、產率69.9%)。該固體C為吲哚[3,2-b]咔唑。
然後，於除氣、氮氣取代之2000毫升的3口燒瓶，加入55%氫氧化鈉4.36g(100.0毫莫耳)、脫水DMF 70毫升，在氮氣氣流中進行攪拌。於其中，花費10分鐘滴入上述固體C 10.4g(40.6毫莫耳)的脫水DMF溶液(150毫升)，滴完後，持續攪拌1小時。然後，以1小時滴入2-氯-4,6-二苯基-1,3,5-三嗪(triazine)20.9g(78.0 毫莫耳)的脫水DMF(300毫升)溶液。滴完後，持續攪拌3小時。然後，加入水900g，過濾所析出的結晶。將所過濾的結晶以水450g進行2次的再成漿洗淨，然後以甲醇450g進行再成漿洗淨。減壓蒸餾除去溶劑，得到褐色結晶42.0g。將其以THF及甲醇進行結晶析出精製後，減壓蒸餾除去溶劑，得到淡褐色固體(化合物114)13.4g(18.6毫莫耳、產率46%)。
APCI-MS, m/z 719 [M+1]+ 熔點498℃。
實施例5
(化合物116的合成) 於除氣、氮氣取代之200毫升的3口燒瓶，加入吲哚[3,2-b]咔唑1.3g(5.1毫莫耳)、第3丁氧化鈉1.4g(14.6毫莫耳)、乙酸鈀8.2mg(0.037毫莫耳)、2,6-二苯基-4-碘吡啶6.4g(17.9毫莫耳)及二甲苯80毫升，於室溫下攪拌1小時。於其中加入三-第3丁基膦64mg(0.32毫莫耳)，於120℃下加熱攪拌40小時。冷卻至室溫後，加入水70毫升，過濾析出物。將所得的固體依序以甲醇、甲苯、三氯甲烷，藉由加熱再成漿精製，得到淡褐色固體(化合物116)1.0g(1.4毫莫耳、產率27.5%)APCI-MS, m/z 715 [M+1]+ 熔點426℃。
實施例6
(化合物2的合成) 於除氣、氮氣取代之1000毫升的3口燒瓶，加入55%氫氧化鈉2.18g(0.056莫耳)、脫水DMF240毫升，在氮氣氣流中進行攪拌。於其中，花費10分鐘滴入11-苯基吲哚[2,3-a]咔唑13.3g(0.04莫耳)的脫水DMF溶液(25毫升)，滴完後，持續攪拌1小時。然後，以1小時滴入2,4,6-三氯-1,3-嘧啶8.8g(0.048莫耳)的脫水DMF(150毫升)溶液。滴完後，持續攪拌3小時。然後，加入水500毫升，過濾所析出的結晶。將所過濾的結晶以水300g進行2次的再成漿洗淨，然後以甲醇300g進行再成漿洗淨。減壓蒸餾除去溶劑，得到純黃色結晶18.2g。所得的結晶不進行精製而用於以下的反應。
然後，於2000毫升的3口燒瓶，加入上述所得的純黃色結晶18.2g(0.038莫耳)、苯硼酸9.73g(0.08莫耳)、四(三苯膦)鈀1.84g(0.0016莫耳)、乙醇150毫升、甲苯450毫升後，進行攪拌。然後，加入碳酸鈉29.8g(0.28莫耳)的水(140毫升)溶液，於85℃下攪拌4小時。冷卻至室溫後，加入水200毫升、甲苯200毫升，分成有機層與水層，將有機層以200毫升的水洗淨。將有機層以硫酸鎂進行脫水，過濾硫酸鎂後，減壓蒸餾除去溶劑。將其以二氯甲烷及乙醇進行結晶析出精製後，減壓蒸餾除去溶劑，得到白色固體(化合物2)5.2g(0.0092莫耳、產率23%)。
APCI-MS, m/z 563 [M+1]+ 熔點252℃。
實施例7
(化合物29的合成) 於除氣、氮氣取代之100毫升的3口燒瓶，加入乙酸鈀(II)0.21g(0.94毫莫耳)、二甲苯(20毫升)、三第3丁基膦0.76g(3.76毫莫耳)，於60℃下加熱攪拌30分鐘。將該溶液送至氮氣氣流下加熱至60℃之吲哚[2,3-a]咔唑4.61g(0.0180莫耳)、4-咔唑基溴苯5.8g(0.018莫耳)及第3丁氧化鈉7.7g(0.080莫耳)的二甲苯(180毫升)溶液中。然後升溫至130℃，於同樣溫度下加熱攪拌5小時。冷卻至室溫後，加入水200毫升。油水分離，將有機層減壓濃縮，得到粗製生成物。將其以二氯甲烷及乙醇進行結晶析出精製後，減壓蒸餾除去溶劑，得到11-(4-咔唑基苯基)吲哚[2,3-a]咔唑4.2g(0.0084莫耳、產率47%)。
然後，於除氣、氮氣取代之200毫升的3口燒瓶，加入55%氫氧化鈉0.42g(0.0096莫耳)、脫水DMF 10毫升，在氮氣氣流中進行攪拌。於其中，花費10分鐘滴入上述11-(4-咔唑基苯基)吲哚[2,3-a]咔唑4.0g(0.008莫耳)的脫水DMF溶液(20毫升)。滴完後，持續攪拌1小時。然後，以1小時滴入2-氯-4,6-二苯基-1,3,5-三嗪(triazine)2.14g(0.008莫耳)的脫水DMF(20毫升)溶液。滴完後，持續攪拌3小時。然後，加入水100g，過濾所析出的結晶。將所過濾的結晶以水100g進行2次的再成漿洗淨，然後以甲醇100g進行再成漿洗淨。減壓蒸 餾除去溶劑，藉由THF/甲醇之結晶析出精製，得到黃色固體(化合物29)3.0g(0.0041莫耳、產率51%)。
APCI-MS, m/z 729 [M+1]+ 熔點319℃。
實施例8
(化合物37的合成) 於除氣、氮氣取代之2000毫升的3口燒瓶，加入55%氫氧化鈉4.80g(110.0毫莫耳)、脫水DMF 70毫升，在氮氣氣流中進行攪拌。於其中，花費10分鐘滴入吲哚[2,3-a]咔唑13.5g(52.7毫莫耳)的脫水DMF溶液(150毫升)。滴完後，持續攪拌1小時後，於其中，以1小時滴入2-氯-4,6-二苯基-1,3,5-三嗪(triazine)29.4g(110.0毫莫耳)的脫水DMF(150毫升)溶液。滴完後，持續攪拌3小時，加入水900g，過濾所析出的結晶。將所過濾的結晶以水450g進行2次的再成漿洗淨，然後以甲醇450g進行再成漿洗淨。減壓蒸餾除去溶劑，得到結晶35.0g。將其藉由THF/甲醇之結晶析出精製，得到黃色固體(化合物37)24g(33.4毫莫耳、產率63.4%)。
APCI-MS, m/z 719 [M+1]+ 熔點426℃。
實施例9
(化合物1的合成) 於除氣、氮氣取代之20毫升的3口燒瓶，加入乙酸鈀(II)0.071g(0.32毫莫耳)、二甲苯(5毫升)、三 第3丁基膦0.32毫升(1.26毫莫耳)，於60℃下加熱攪拌30分鐘。將該溶液送至氮氣氣流下加熱至60℃之11-苯基吲哚[2,3-a]咔唑1.99g(0.0060莫耳)、2,6-二苯基-4-碘吡啶2.46g(0.0069莫耳)及第3丁氧化鈉2.57g(0.0267莫耳)的二甲苯(60毫升)溶液中。然後升溫至130℃，於同樣溫度下加熱攪拌5小時。冷卻至室溫後，加入水70毫升。油水分離，將有機層減壓濃縮，得到粗製生成物4.85g。將其以二氯甲烷及乙醇進行結晶析出精製後，減壓蒸餾除去溶劑，得到白色固體(化合物1)1.43g(0.0025莫耳、產率36%)。
APCI-MS, m/z 562 [M+1]+ 熔點277℃、287℃。
實施例10
製作圖1中，追加電子注入層之構成的有機EL元件。於形成有膜厚150nm的ITO所構成的陽極之玻璃基板上，各薄膜以真空蒸鍍法，在真空度4.0×10-4 Pa下層合。首先，於ITO上，形成20nm厚度的銅酞青(CuPc)作為電洞注入層。然後於形成40nm厚度的NPB，作為電洞傳輸層。然後，於電洞傳輸層上，將作為發光層之化合物3與Ir (ppy)3 從不同的蒸鍍源進行共蒸鍍，形成35nm的厚度。此時，Ir (ppy)3 的濃度為7.0重量%。然後，形成40nm厚度的Alq3作為電子傳輸層。再於電子傳輸層上，形成0.5nm厚度的氟化鋰(LiF)作為電子注入層。最後於電子注入層上，形成170nm厚度的鋁(Al)作為電極 ，而製作完成有機EL元件。
於所得的有機EL元件，連接外部電源，施以直流電壓時，確認具有如表3所示的發光特性。於表3中，亮度、電壓及發光效率係表示在10mA/m2 的值。而且，元件發光光譜的最大波長為517nm，得知得到來自Ir (ppy)3 的發光。
實施例11~16
除使用實施例4~8所得的化合物(化合物第114、116、2、29、37及1號)作為發光層的主成分以外，與實施例10同樣地製作有機EL元件。於表3中，表示發光特性。實施例4~8所得的化合物(化合物第114、116、2、29、37及1號)全部，確認可得來自Ir (ppy)3 的發光。
〔產業上的利用可能性〕
本發明的有機EL元件，可在低電壓下以高亮度‧高效率發光。所以，根據本發明的有機EL元件，被視為朝產生作為平面面板‧顯示器(例如OA用電腦用、壁掛式電視)、車用顯示元件、手機顯示、面發光體之特徵的光源(例如影印機的光源、液晶顯示器、儀器類的背光源)、告示板、標誌燈的應用，其技術的價值非常大。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧電洞注入層
4‧‧‧電洞傳輸層
5‧‧‧發光層
6‧‧‧電子傳輸層
7‧‧‧陰極
圖1為表示有機EL元件的一例之模型式剖面圖。

Claims (10)

  1. 一種有機電場發光元件用化合物，其特徵為：以下述一般式(1)所示的有機電場發光元件用化合物， 此處，環A表示與鄰接環B在任意位置進行縮合之式(1a)所表示的雜環，環B表示以式(1b)所示之芳香族烴環，X表示CH或N，X中至少之一為氮原子，Ar1 ~Ar3 表示獨立之非縮環構造的取代或未取代之芳香族烴基或芳香族雜環基，Ar2 或Ar3 可與含有X的環形成縮合環，R為氫或1價取代基。
  2. 如申請專利範圍第1項之有機電場發光元件用化合物，其中一般式(1)中，R為獨立之氫或烷基、芳烷基、烯基、炔基、氰基、二烷基胺基、二芳基胺基、二芳 烷基胺基、胺基、硝基、醯基、烷氧基羰基、羧基、烷氧基、烷基磺醯基、鹵烷基、羥基、醯胺基、取代或未取代的芳香族烴基或芳香族雜環基。
  3. 如申請專利範圍第1項之有機電場發光元件用化合物，其中一般式(1)中，R為獨立之氫、取代或未取代的碳數5~18的芳香族烴基或碳數3~17的芳香族雜環基所構成。
  4. 如申請專利範圍第1項之有機電場發光元件用化合物，其中一般式(1)中，Ar1 ~Ar3 為獨立之取代或未取代的苯基、或取代或未取代的碳數2~5的芳香族雜環基所構成。
  5. 如申請專利範圍第1項之有機電場發光元件用化合物，其係以下述一般式(2)或(3)所表示之化合物， 此處，X及Ar1 ~Ar3 與式(1)及(1a)中的X及Ar1 ~Ar3 意義相同。
  6. 一種有機電場發光元件，其特徵為：具有含如申請專利範圍第1~5項中任一項之有機電場發光元件用化合物之有機層。
  7. 如申請專利範圍第6項之有機電場發光元件，其中該含有機電場發光元件用化合物之有機層，係選自發光層、電洞傳輸層、電子傳輸層及電洞阻隔元件層中的至少一層。
  8. 如申請專利範圍第6項之有機電場發光元件，其中該含有機電場發光元件用化合物之有機層，係於基板上所層合的陽極與陰極之間具有發光層之有機電場發光元件的發光層，該發光層含有磷光發光性摻雜物及吲哚咔唑(indolocarbazole)作為主體材料。
  9. 如申請專利範圍第8項之有機電場發光元件，其係於陽極與發光層之間具有電洞注入傳輸層，於陰極與發光層之間具有電子注入傳輸層所構成。
  10. 如申請專利範圍第9項之有機電場發光元件，其 係於發光層與電子注入傳輸層之間具有電洞阻隔層所構成。
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US20100187977A1 (en) 2010-07-29
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