TWI390006B - Organic EL materials with aluminum clamps - Google Patents

Organic EL materials with aluminum clamps Download PDF

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TWI390006B
TWI390006B TW093123403A TW93123403A TWI390006B TW I390006 B TWI390006 B TW I390006B TW 093123403 A TW093123403 A TW 093123403A TW 93123403 A TW93123403 A TW 93123403A TW I390006 B TWI390006 B TW I390006B
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organic
aluminum
reaction
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Shinji Matsuo
Hiroshi Miyazaki
Taishi Tsuji
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Nippon Steel Chemical Co
Pioneer Corp
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Description

有機EL材料用之鋁鉗合錯合物
本發明為有關一種有機電致發光元件(以下，簡稱有機EL元件)，及作為其發光層內所含有之材料的鋁鉗合錯合物。
一般而言，使用有機材料構成顯示面板之各種有機EL元件，係具有於顯示面之玻璃基板上，以薄膜形式依序層合作為透明電極之陽極、含有發光層之複數有機材料層、由金屬電極所形成之陰極之構造。有機材料層中，除有機發光層以外，尚包含電子洞注入層、電子洞輸送層等具有電子洞輸送能之材料所形成之層，或包含電子注入層、電子輸送層等具有電子輸送能之材料所形成之層，及由具有前述結構之有機EL元件。其中電子注入層亦包含無機化合物。
於對於有機發光層及具有電子或電子洞之輸送層的有機EL元件施加電場時，則電子洞由陽極、電子由陰極注入其中。有機EL元件，為利用此電子與電子洞於有機發光層再結合形成激動子，再使其回復至基底狀態時所釋出之發光之元件。為達成發光之高效率化或元件得以安定驅動之結果，發光層多使用色素作為客體材料進行摻雜而得。
近年來，發光層除螢光材料以外，尚有利用磷光材料 之提案。於有機EL元件之發光層中，電子與電子洞經再結合後之一重項激動子與三重項激動子之發生率一般約為1：3，故利用三重項激動子之磷光之元件較使用一重項激動子之螢光之元件而言，可達成其3至4倍之發光效率。
又，為提高有機EL元件之低電力性、發光效率與驅動安定性等，也有提出於有機發光層至陰極之間設置可限制由有機發光層向電子洞移動之電子洞阻滯層之方案。此電子洞阻滯層可使電子洞有效率的儲存於發光層中，因而可提高與電子之再結合率，而可使發光達到高效率化。其中，已有提出使用菲繞啉衍生物或三唑衍生物作為電子洞阻滯層材料較為有效之報告。
【專利文獻1】特開4-206685號公報 【專利文獻2】特開2001-237079號公報 【專利文獻3】特開2001-284056號公報
於JP04-206685A中，揭示一種使用羥基喹啉化合物與酚性化合物之鋁錯合物(以下簡稱AlQ2OR)作為藍光釋出性發光材料之有機EL材料使用為極有用之報告。此AlQ2OR為具有2分子之8-羥基喹啉化合物與1分子酚性化合物，與1個鋁原子形成錯合物之結構。
JP04-206685A中，則揭示使AlQ2OR存在於電子輸送層間，並使其發光之例示。
JP2001-237079A中，則揭示一種使AlQ2OR存在於電子輸送層間，並使其產生磷光發光或螢光發光之有機EL材料。又，JP2001-284056A中，則揭示於含有磷光材 料之發光層與電子輸送層間設置電子洞阻礙層，並使AlQ2OR存在於其中之磷光發光的有機EL元件之報告。
JP2001-237079A與JP2001-284056A中，AlQ2OR之具體例如，羥基喹啉化合物為2-甲基-8-羥基喹啉，酚性化合物為4-苯基酚之化合物所得之((1,1’-聯苯基)-4-酮鹽)雙(2-甲基-8-喹啉鹽-N1,08)鋁(以下簡稱BAlq)等例示。其中，BAlq雖具有優良之耐久性，但卻具有因Ip不大，故電子洞阻滯性能劣化之缺點。因此，作為電子洞阻止層之BAlq，於使用tris(8-hydroxyquinolato N1,08)aluminium(以下簡稱Alq3)作為電子輸送層時，可使電子輸送層產生發光。但於利用紅色磷光發光之有機EL元件中，Alq3之發光(綠色)之色度則為不佳。因此，於使用客體材料為磷光材料所得發光層之有機EL元件中，主體材料使用AlQ2OR，即可在維持良好發光特性下，而達成具有更長驅動壽命之結果。
但，於使用AlQ2OR之元件中，常因使用壽命之分歧，而造成實用上極大之障礙，目前對於其使用壽命分歧之原因仍未完全明瞭。因此，目前除以使用具有更高信賴度之實用元件作為製造上不可欠缺的材料為管理指標以外，對於改善使用壽命之指標仍處於研究之狀態。
本發明之目的為提供一種含有作為材料之AlQ2OR的有機EL元件，其除可釋明影響元件壽命之原因，提供解 決手段，並提供製造具有高度信賴性實用元件上所不可欠缺之材料的管理指標結果，而可使有機EL元件產生優良機能，此外可降低經時發光強度之劣化，且具有優良信賴性之具有實用程度之高品質有機EL材料，及使用其所得之有機EL元件。
本發明者們，對於開發實用且耐用之由AlQ2OR所得之有機EL材料作深入研究結果，得知依一般方法所製得之AlQ2OR中含有特徵之雜質，並經由闡明前述雜質之含量與有機EL元件之耐久性間之關聯性結果，而完成本發明。
本發明，為於式(1)所示鋁鉗合錯合物中，作為雜質的式(2)所示化合物之量為350wtppm以下之有機EL材料用之鋁鉗合錯合物，
式(1)與式(2)中，Ar1 為1至2環之伸芳基，Ar2 為1至2環之芳基，Ar1 與Ar2 中所含芳香族環之合計數目為2至4環，Ar1 與Ar2 中所含芳香族環之數目為2以上時，前述芳香族環可為縮合環；R1 至R6 為獨立之氫或碳數1至8之烴基，又，X為鹵素；又，式(1)與式(2)中，同一記號為具有相同之意義。
其中，伸芳基與芳基(Ar1 與Ar2 )必須直接結合，Ar1 與Ar2 可具有核取代之結構。Ar1 與Ar2 各自以H-Ar1 -H與Ar2 -H表示時，則分別為苯、萘、聯苯或其烷基取代基等。烷基取代基之烷基例如為碳數1至6之烷基(低級烷基)為佳，其取代數以3以下為佳。其中又以Ar1 為伸萘基或伸苯基，Ar2 為萘基或苯基為更佳。又，Ar1 與Ar2 中所含之芳香族環之合計數目以2至3環為較佳。
式(1)與式(2)中，R1 至R6 為獨立之氫或碳數1至8之烴基，烴基例如烷基、烯基等，較佳為碳數1至3之烷基。但，芳基或含芳基之基除外。又，X以Br、I或Cl為佳。
上述鋁鉗合錯合物，為將異丙氧化鋁依序與喹啉酚衍生物及以HO-Ar1 -Ar2 表示之酚性化合物反應所得者。前述鋁鉗合錯合物，於陽極與陰極間含有由有機化合物所得發光層之有機電致發光元件中，作為發光層之主體材料使用。
以下，將對本發明作詳細之說明。
由式(1)所示本發明之有機鋁鉗合錯合物(亦稱為AlQ2OR)所得之有機EL材料，於作為有機EL原劑閃用時，較佳為作為發光層之主體材料使用。AlQ2OR之製造方法，例如JP04-206685A所揭示之內容般，於乙醇溶劑中，依序與異丙氧化鋁與喹啉酚衍生物、酚性化合物反應，使其錯合物化之方法等。
此時，作為配位機使用之喹啉酚衍生物之合成方法，例如可採用芳基胺化合物與鹵芳基化合物進行烏耳曼反應以合成等，於8-羥基喹啉等常用化合物時，則可使用市售物。
又，酚性化合物之合成，例如將有機硼化合物與鹵化物或三氟甲基磺酸酯化合物進行鈴木偶合反應(Ar1 -X or Ar1 -OTf+Ar2 -B(OH)2 →Ar1 -Ar2 )以外，例如使用二偶氮鎓鹽進行反應(Ar1 +Ar2 -N2 Cl→Ar1 -Ar2 )、將鹵化物於同觸媒下進行反應之烏耳曼反應(Ar1 -X+Ar2 -X→Ar1 -Ar2 )、使用格利雅試劑之利用各種有機金屬化合物所進行之(Ar1 -X+Ar2 -MgX→Ar1 -Ar2 、Ar1 -X+Ar2 -Li→Ar1 -Ar2 、Ar1 -X+Ar2 -ZnX→Ar1 -Ar2 、Ar1 -X+Ar2 -SnMe3 →Ar1 -Ar2 ) 等已知交又偶合反應。又，上述Ar1 與Ar2 為芳基。但，本反應中常會產生羥基芳基鹵化物等副產物或產生殘留而未反應等反應狀態。
酚性化合物，例如以HO-Ar1 -X所示之化合物與(Ar2 )a -Y所示化合物反應之方法為佳。其中Ar1 、Ar2 與X具有與式(1)中之Ar1 、Ar2 與X具有相同意義。又，Y為Cu、X、Li、B(OH)2 、MgX、ZnX、SnMe3 等，X為鹵素，a為1至10之整數，a為對應Y之價數，此反應中，HO-Ar1 -X所示之酚性化合物與，(X)a -Y所示之化合物或其分解產物係以反應產物方式製得。此反應中，一般於有機溶媒中進行，將其於酸性條件中，以水萃取之意思係指，將標的之酚性化合物於有機溶劑相中，將含有鹵素之化合物移至水相之意。此方法可以對標的之酚性化合物僅以水洗之方式即可精製之精製方法。
又，所得之酚性化合物，於作為鋁鉗合錯合物之原料使用時，因於鋁鉗合錯合物之合成反應中會產生副產物之醇類，而於反應後需進行洗淨等精製處理，此點為酚性化合物之精製上為極需注意之部份。
又，於合成HO-Ar1 -Ar2 所示酚性化合物之際，HO-Ar1 -X所示鹵化物若殘留數重量%~十數重量%時，則對於合成之酚性化合物之精製若僅以水萃取或以水洗方式之精製方法將會有未能充分將其去除之困難點。又，由前述含鹵化物之酚性化合物合成式(1)所示之AlQ2OR時，將會生成式(2)所示副產物(以下亦稱為AlQ2X)，此 反應物於精製時若依一般之醇洗淨等方法將會有未能充分去除之困難點。
因此，使用含有一定量以上副產物之鋁鉗合錯合物，於製造有機EL元件時，將會成為發光強度之劣化大幅提高之原因。故，一般於製造有機EL元件之際，於基板上之有機層上蒸鍍越多前述材料時，AlQ2X與AlQ2OR亦同時蒸鍍於其上，故可推測其含於有機EL元件之有機層之中。
AlQ2OR中之雜質AlQ2X之含量，若低於350ppm以下時，已可使劣化速度低於不會干涉實際使用之程度，故若於100ppm以下之痕量時，則可製造賦予實用上具有充分發光壽命之有機EL元件。
將AlQ2X之含量降低至350ppm之方法，例如(1)於合成HO-Ar1 -Ar2 所示酚性化合物之際，於反應結束後之分離、精製步驟中，除經過水洗、蒸餾分離以外，再配合使用有機溶媒進行再結晶等組合方式，將酚性化合物中雜質之含量降低至350ppm以下之方法；(2)依序將醇鋁錯合物、喹啉酚衍生物與酚性化合物進行反應以合成鋁鉗合錯合物之際，於反應結束後之分離、精製步驟中，除經過醇洗淨以外，再配合昇華精製等組合方式，將雜質之含量降低至350ppm以下之方法；(3)組合前述(1)與(2)所得之方法；(4)於合成HO-Ar1 -Ar2 -H所示酚性化合物之際，將未反應之HO-Ar1 -X所示之鹵化物限定至一定量以下之方式，使含有HO-Ar1 -X與Ar2 之化合物的莫耳 比較理論量為低或提高反應溫度等，於充分之反應時間下使前者之反應率達90%以上之方法。其中又以(3)之方法或將反應所得HO-Ar1 -Ar2 所示酚性化合物以再結晶精製，且對使用其所得之鋁鉗合錯合物進行昇華精製之方法最為有效。
HO-Ar1 -X所示鹵化物之分析方法，例如可使用HPLC進行，Br化合物之檢測下限為0.5ppm(wt)。此鹵化物之含量低於350ppm時，可使最後所得之鋁鉗合錯合物中AlQ2X之含量達350ppm以下。又，有關最後所得之鋁鉗合錯合物中AlQ2X之分析方法，因前述鋁鉗合錯合物於高溫下並不穩定，於通過色層分析中維持在高溫的柱體時將產生分解，故直接測定其含量仍存在相當困難度，但其可使用離子色層分析以測定鹵素含量，故可再將其換算為AlQ2X之含量。因此，本發明中有關式(2)所示AlQ2X之含量，為測定X表示之鹵素，再將其換算所得之值。
又，本發明之有機EL材料用之化合物的鋁鉗合錯合物中，為對式(2)所示化合物含量作350wtppm以下之品質管理，其他例如於生產、出貨或使用階段中，只要對此含量作測定管理即可。
一般去除製造本發明之錯合物時所使用之作為原料的酚性化合物於製造時所常產生副產物之鹵化物的方法，通常為使用再結晶、晶析、蒸餾、吸附等方法，其中又以再結晶為簡便、確實之方法而為較佳。又，製造喹啉酚衍生物時亦會生成副產物之鹵化物，一般可使用精製方式去除 ，可採用與上述相同之精製方法。去除之標準，為使喹啉酚衍生物與酚性化合物中之鹵素化合物之含量降至350wtppm以下，較佳為降低至檢測下限以下。
未對上述喹啉醇衍生物或酚性化合物進行精製時，最終製品之式(1)所示AlQ2OR中多含有達數~十數重量%之式(2)所示AlQ2X，於經過昇華精製等步驟後，可使其降低至1/10以下程度。
一般只要確實執行喹啉醇衍生物與酚性化合物之配位基階段之精製，與最後製品之鋁錯合物階段之精製中任一種精製方式時，即可達到本發明之目的，又以同時使用2種精製方式為更佳。
經使用本發明之有機EL用材料，於長時間驅動下可減少發光強度之劣化，而可製得具有優良耐久性之有機EL元件。
[實施發明之最佳形態]
以下為適合作為本發明有機EL材料用之鋁鉗合錯合物之AlQ2OR，以化合物(11)至(23)為例示，但並不僅限定於此。
本發明之鋁鉗合錯合物，可作為有機EL材料使用。此有機EL材料，可用於有機EL元件之電子輸送層、電子洞阻礙層、發光層等，其中又以用於發光層為最佳。更有利者為，於具有主體材料與客體材料之發光層中作為主體材料使用。此時，客體材料可使用釕、銠、鈀、銀、錸、鋨、銥、鉑或金等所選出之磷光性有機貴金屬錯合物化合物。含有前述主體材料與客體材料之有機EL元件，其為經時性發光強度之劣化較少，且具有信賴性之優良元件。
上述客體材料之磷光性有機貴金屬錯合物化合物，以化合物(31)至(40)為例示，但並不僅限定於此。
以下將本發明之有機EL元件之一例示，以參照說明有機EL元件之層結構的截面圖之圖1方式作說明。
圖1所示之有機EL元件，其為由玻璃等透明基板1、陽極2、電子洞輸送層3、發光層4、電子輸送層6與陰極7所構成。其為於玻璃等透明基板1上，層合透明陽極2、有機化合物所得之電子洞輸送層3、發光層4、電子輸送層6及低功函數材料之材料例如金屬陰極7層合所得者。具體而言，例如具有陽極為使用銦錫氧化物(以下簡稱ITO)、電子洞輸送層使用4,4’-雙(N-萘基-N-苯基-胺基)聯苯(以下簡稱NPB)(Ip=5.4eV)、發光層使用AlQ2OR所得之有機主體材料、電子輸送層使用Alq3、陰極使用 鋁等結構。
圖1所示有機EL元件以外之其他有機EL元件結構，例如於電子輸送層6與陰極7之間，層合由Li2 O等電子注入層之薄膜層，再進行成膜者亦佳。又，例如於陽極2與電子洞輸送層3之間，層合由銅酞菁(以下簡稱CuPc)等卟啉化合物等電子洞注入層之薄膜層，再進行成膜者亦佳。
陽極2，為由ITO等功函數較大之導電性材料所製得，厚度約為1000至3000左右，或使用厚度約為800至1500左右之金。又，使用金作為電極材料時，電極呈現半透明狀態。陰極與陽極中，只要其中任一為透明或半透明即可。又，陰極7，例如可使用鋁、鎂、銦、銀或各種合金等功函數較小之金屬所製得之厚度約為100至5000左右者。
電子洞輸送層3中所含之成分，只要具有電子洞輸送能力之物質即可使用。例如下示化合物(41)至(66)者。
作為構成發光層之主體材料使用之鋁鉗合錯合物，例如前述AlQ2OR等，作為客體材料使用之磷光性有機貴金屬錯合物化合物，例如前述有機貴金屬錯合物化合物。但，必要時，於不損及本發明之效果之範圍下，可再少量添加其他材料。又，對主體材料之客體材料之使用比例(wt)，一般以97：3至70：30左右為佳。
構成電子輸送層6之材料，例如可使用下述化合物(71)至(89)中所選出之公知材料。
又，上述式中，t-Bu為三級丁基。又，具有電子輸送能力之有機材料，例如下述化合物(90)至(125)所示之鋁鉗合物。
又，可用於電子輸送層6之具有電子輸送能力之有機材料，例如由下述化合物(126)至(134)所示之菲繞啉衍生物所選出者。
以下，本發明將以實施例為基礎，作更詳細之說明。其中，「%」與「ppm」分別表示「wt%」與「wtppm」之意。又，酚性化合物中鹵化物之分析，為使用HPLC進行(Br化合物之檢測界限為0.5ppm)。鋁鉗合錯合物中之AlQ2X之分析，為使用離子色層分析儀測定鹵素含量(檢測界限為50ppm)，再將其換算為AlQ2X之方式進行。
合成例1
於裝置冷卻管、溫度計、攪拌機之三口燒瓶中，投入6-溴-2-萘酚26.8g、四-三苯基次膦酸鈀4.6g、甲苯100ml後，於50℃下進行攪拌。於固體成分幾乎溶解之際，加入溶解有苯基硼酸14.6g之100ml乙醇溶液，再進行攪拌。於溶液混合時，投入含有碳酸鈉30g之100ml水溶液，加熱至迴流溫度後，再進行1小時攪拌。反應結束後，將稀鹽酸加至水層呈弱酸性為止，隨後回收有機層，以減壓蒸餾方式去除溶媒。所得粗產物中再加入50ml甲苯進行再 結晶，將濾取所得之結晶以甲苯洗淨，於80℃下進行減壓乾燥，得11.9g之6-苯基-2-萘酚。經使用HPLC測定未反應之6-溴-2-萘酚，得知並未檢測出結果。
合成例2
於三口燒瓶中，投入2-甲基-8-喹啉酚(純度98.0%以上)8.3g、異丙氧基鋁10.7g、脫水乙醇290ml後，於氮氣流下加熱至迴流溫度後，再進行1小時攪拌。將反應液冷卻至室溫，以氟鎂石過濾以去除不溶成分。將此濾液於室溫下攪拌中，緩緩加入2-甲基-8-喹啉酚8.3g、溶解有依合成例1所得6-苯基-2-萘酚11.5g之脫水乙醇75ml，再攪拌1小時。濾取所產生之沉澱，依序以乙醇、甲醇洗淨，於70℃下減壓乾燥5小時，得化合物(14)27.9g。經使用離子色層分析測定Br，得知並未檢測出結果，又，相當於化合物(14)之苯基被Br取代之式(2)所示化合物：雙-(2-甲基-8-喹啉鹽)-鋁-(III)(以下簡稱BQMA)之雜質，經計算結果為低於350ppm。
合成例3
於三口燒瓶中，投入6-溴-2-萘酚17.9g、四-三苯基次膦酸鈀4.6g、甲苯200ml後，於室溫下進行攪拌。於固體成分幾乎溶解之際，加入溶解有苯基硼酸9.8g之200ml乙醇溶液，再進行攪拌。其後投入含有碳酸鈉20g之200ml水溶液，於室溫下進行1小時攪拌。反應結束後，將稀鹽 酸加至水層呈弱酸性為止，隨後回收有機層，以減壓蒸餾方式去除溶媒。得22g之6-苯基-2-萘酚。經測定未反應之6-溴-2-萘酚的殘留量，得知為16%。
合成例4
於三口燒瓶中，投入2-甲基-8-喹啉酚7.2g、異丙氧基鋁9.2g、脫水乙醇270ml後，於氮氣流下加熱至迴流溫度後，再進行1小時攪拌。將反應液冷卻至室溫，以氟鎂石過濾以去除不溶成分。將此濾液於室溫下攪拌中，緩緩加入2-甲基-8-喹啉酚7.2g、溶解有依合成例3所得6-苯基-2-萘酚9.9g之脫水乙醇50ml，再攪拌1小時。濾取所產生之沉澱，依序以乙醇、甲醇洗淨，於70℃下減壓乾燥5小時，得化合物(14)14g。計算得知此化合物(14)中Br量為2000ppm，BQMA為500ppm。
合成例5
將合成例2所得之化合物(14)再進行昇華精製。昇華精製，為將合成例2所得之化合物2.0g，使用由玻璃製外筒與玻璃製內筒所構成之具有加熱部與收集部之昇華精製裝置進行精製。收集部，為使用所供應之氮氣進行冷卻。並使用真空幫浦將反應系內減壓至2.0Torr，將加熱部溫度設定為360℃，於收集部之玻璃內壁上收集化合物。收集部所收集之化合物(14)為1.1g，並未檢測出Br，BQMA經計算結果為低於350ppm。
合成例6
於300ml三口燒瓶中，投入2-甲基-8-喹啉酚4.33g、異丙氧基鋁5.56g、脫水乙醇160ml後，於氮氣流下加熱至迴流溫度後，再進行1小時攪拌。將反應液冷卻至室溫，以氟鎂石過濾以去除不溶成分。將此濾液於室溫下攪拌中，緩緩加入2-甲基-8-喹啉酚4.33g、溶解有6-溴-2-萘酚6.07g之脫水乙醇30ml，再攪拌1小時。濾取所產生之沉澱，依序以乙醇、甲醇洗淨，於70℃下減壓乾燥5小時，得BQMA14g。
合成例7
於三口燒瓶中，投入o-胺基酚33g、濃鹽酸207g，加熱至迴流溫度後，進行1小時之攪拌。再於加熱迴流下以2小時時間緩緩加入純度為65%之3-戊烯-2-酮51g後，再進行2小時之反應。反應結束後，冷卻至室溫，再加入48% NaOH水溶液300ml，使水相呈鹼性。再加入乙酸乙酯以回收有機層，以減壓蒸餾方式去除溶媒。將所得之粗產物使用柱體色層分析儀精製，再使用己烷進行再結晶，將濾取所得之結晶使用己烷洗淨，於80℃下進行減壓乾燥，得18.9g之2,4-二甲基-8-萘酚。
合成例8
於三口燒瓶中，投入合成例7所得2,4-二甲基-8-萘酚3.5g、異丙氧基鋁4.1g、脫水乙醇150ml後，於氮氣流下 加熱至迴流溫度後，再進行1小時攪拌。將反應液冷卻至室溫，以氟鎂石過濾以去除不溶成分。將此濾液於室溫下攪拌中，緩緩加入2,4-二甲基-8-萘酚3.5g、溶解有依合成例1所得6-苯基-2-萘酚4.7g之脫水乙醇100ml，再攪拌1小時。濾取所產生之沉澱，依序以乙醇、甲醇洗淨，於70℃下減壓乾燥5小時，得化合物(23)9.0g。使用離子色層分析儀分析結果，並未檢測出Br。又，相當於化合物(23)之苯基被Br取代之式(2)所示化合物：雙-(2,4-二甲基-8-喹啉鹽)(6-溴-2-萘鹽)-鋁-(III)(以下簡稱BDQMA)之雜質，經計算結果為低於350ppm。
合成例9
於三口燒瓶中，投入6-溴-2-萘酚26.8g、四-三苯基次膦酸鈀4.6g、甲苯200ml後，於50℃下進行攪拌。於固體成分幾乎溶解之際，加入溶解有2-萘硼酸20.6g之100ml乙醇溶液，再進行攪拌。於溶液混合之際，投入含有碳酸鈉30g之100ml水溶液，加熱至迴流溫度後，進行1小時攪拌。反應結束後，將稀鹽酸加至水層呈弱酸性為止，隨後回收有機層，以減壓蒸餾方式去除溶媒。所得粗產物中，加入甲苯、乙酸乙酯後進行再結晶，將濾取所得之結晶以甲苯洗淨，於80℃下進行減壓乾燥，得15.6g之6-(2-萘基)-2-萘酚。經測定未反應之6-溴-2-萘酚的殘留量結果並未測得。
合成例10
於三口燒瓶中，投入2-甲基-8-喹啉酚8.3g、異丙氧基鋁10.7g、脫水乙醇290ml後，於氮氣流下加熱至迴流溫度後，再進行1小時攪拌。將反應液冷卻至室溫，以氟鎂石過濾以去除不溶成分。將此濾液於室溫下攪拌中，緩緩加入2-甲基-8-喹啉酚8.3g、溶解有依合成例9所得6-(2-萘基)-2-萘酚14.1g之脫水乙醇75ml，再攪拌1小時。濾取所產生之沉澱，依序以乙醇、甲醇洗淨，於70℃下減壓乾燥5小時，得化合物(15)28.7g。並未檢測出Br，化合物(15)之萘基被Br取代之BQMA，經計算結果為低於350ppm。
合成例11
將合成例8所得之2.0g化合物(23)再使用合成例5所使用之昇華精製裝置進行昇華精製。其為使用真空幫浦將反應系內減壓至2.0Torr，將加熱部溫度設定為370℃後，於收集部之玻璃內壁上收集化合物。收集部所收集之化合物(23)為1.2g，並未檢測出Br，雜質之BDQMA經計算結果為低於350ppm。
合成例12
將合成例10所得之2.0g化合物(15)再使用合成例5所使用之昇華精製裝置進行昇華精製。其為使用真空幫浦將反應系內減壓至2.0Torr，將加熱部溫度設定為380℃後 ，於收集部之玻璃內壁上收集化合物。收集部所收集之化合物(15)為1.1g，並未檢測出Br，雜質之BQMA經計算結果為低於350ppm。
合成例13
於三口燒瓶中，投入合成例7所製得之2,4-二甲基-8-喹啉酚3.5g、異丙氧基鋁4.1g、脫水乙醇150ml後，於氮氣流下加熱至迴流溫度後，再進行1小時攪拌。將反應液冷卻至室溫，以氟鎂石過濾以去除不溶成分。將此濾液於室溫下攪拌中，緩緩加入2,4-二甲基-8-喹啉酚3.5g、溶解有6-溴-2-萘酚4.5g之脫水乙醇100ml，再攪拌1小時。濾取所產生之沉澱，依序以乙醇、甲醇洗淨，於70℃下減壓乾燥5小時，得BDQMA 14g。
使用上述合成例所得之化合物調製下述樣品1至5。
樣品1：合成例2所得之化合物(14)樣品2：合成例4所得之化合物(14)樣品3：合成例5所得之化合物(14)樣品4：合成例2所得之化合物(14)中添加1000ppm合成例6所得之BQMA樣品5：合成例2所得之化合物(14)中添加10000ppm合成例6所得之BQMA樣品6：合成例11所得之化合物(23)樣品7：合成例12所得之化合物(15)樣品8：合成例11所得之化合物(23)中添加 1000ppm合成例13所得之BDQMA樣品9：合成例12所得之化合物(15)中添加1000ppm合成例6所得之BQMA
又，樣品2、4、5、8與9為作為比較之樣品。
實施例1
於ITO陽極上，將CuPc以蒸鍍速度為3/s之速度形成厚度250之膜，而形成電子洞注入層。其次，於CuPc電子洞注入層上，將NPB以蒸鍍速度為3/s之速度形成厚度550之膜，而形成電子洞輸入層。其次，於NPB之電子洞輸送層上，將作為有機主體材料之上述樣品1，與發出紅色磷光之有機客體材料之上述化合物(31)：2,3,7,8,12,13,17,18-octaethyl-21H,23H-prophine Platium(II)(以下簡稱PtOEP)使用不同蒸鍍源共蒸鍍而得厚度475之膜，而形成發光層。此時，發光層中有機客體材料之濃度為7%。
其次，於此發光層上，將Alq3以蒸鍍速度為3/s之速度形成厚度300之膜，而形成電子輸送層。其次，再於Alq3電子輸送層上，將作為電子注入層之氧化鋰(Li2 O)以蒸鍍速度為0.1/s之速度蒸鍍10，再於其上將作為陰極之鋁(Al)以10/s之速度層合1000，而製得有機EL元件。
實施例2
除將樣品1以樣品3代替以外，其他皆依實施例1相同方法製得有機EL元件。
比較例1至3
於有機主體材料中，除將樣品1以樣品2、4或5代替以外，其他皆依實施例1相同方法製得有機EL元件。
對於依上述實施例與比較例所得之有機EL元件，測定以7mA/cm2 驅動時，亮度衰減50%時所需要的時間。其結果如表1所示。
由表1得知，雜質BQMA之含量，與發光之衰減具有極強烈之關係，此雜質之含量於350ppm以下之範圍中，可顯著的改善發光衰減率之問題。
實施例3
於ITO陽極上，將CuPc以蒸鍍速度為3/s之速度形成厚度250之膜，而形成電子洞注入層。其次，於CuPc電子洞注入層上，將NPB以蒸鍍速度為3/s之速度形成厚度550之膜，而形成電子洞輸入層。其次，於NPB之電子洞輸送層上，將作為有機主體材料之上述樣品1，與發出紅色磷光之有機客體材料之PtOEP，使用不同蒸鍍源共蒸鍍而得厚度475之膜，而形成發光層。此時，發光層中之PtOEP之濃度為7%。
其次，於此混合發光層上，將Alq3以蒸鍍速度為3/s之速度蒸鍍為厚度300之膜，而形成電子輸送層。其次，再於Alq3電子輸送層上，將作為電子注入層之氧化鋰以蒸鍍速度為0.1/s之速度蒸鍍10，再於其上將作為陰極之鋁以10/s之速度層合1000，而製得有機EL元件。
實施例4至5
除將樣品1以樣品6或7代替以外，其他皆依實施例3相同方法製得有機EL元件。
比較例4至8
除將樣品1以樣品2、4、5、8或9代替以外，其他皆依實施例3相同方法製得有機EL元件。
對於依上述實施例與比較例所得之有機EL元件，測定以5.5mA/cm2 驅動時，亮度衰減50%時所需要的時間。 其結果如表2所示。
由表2得知，雜質BQMA或BDQMA之含量，與發光之衰減具有相當密切之關係，此雜質之含量於350ppm以下之範圍中，可顯著的改善發光衰減率之問題。
1‧‧‧玻璃基板
2‧‧‧透明電極(陽極)
3‧‧‧有機電子洞輸送層
4‧‧‧有機發光層
6‧‧‧電子輸送層
7‧‧‧金屬電極(陰極)
圖1為有機EL元件之層結構之一例示的結構圖。
1‧‧‧玻璃基板
2‧‧‧透明電極(陽極)
3‧‧‧有機電子洞輸送層
4‧‧‧有機發光層
6‧‧‧電子輸送層
7‧‧‧金屬電極(陰極)

Claims (4)

  1. 一種式(2)所示化合物之量為350wtppm以下之有機EL材料用之鋁鉗合錯合物之製造方法，其特徵為，使異丙氧化鋁依序與喹啉酚衍生物及HO-Ar1 -Ar2 所示之酚性化合物反應，以製造式(1)所示鋁鉗合錯合物之製造方法中，上述酚性化合物為由HO-Ar1 -X所示之化合物與(Ar2 )a -Y所示化合物反應所得者，且將喹啉酚衍生物及酚性化合物中所含有之HO-Ar1 -X所示化合物之量精製至350wtppm以下後，再供應於反應之方法， (式(1)與式(2)中，Ar1 為2環之伸芳基，Ar2 為1至2環之芳基，Ar1 與Ar2 中所含芳香族環之合計數目為3至4環，該些芳香環可相互縮合；R1 至R6 各自獨立地表示氫或碳數1至8之烴基，X表示鹵素；又上述HO-Ar1 -Ar2 、HO-Ar1 -X，及(Ar2 )a -Y中，Ar1 、Ar2 及X內容係與上述為相同之內容；Y表示Cu、X、Li、B(OH)2 、MgX、ZnX、SnMe3 ，其中，X表示鹵素，a表示1~10之整數)。
  2. 一種式(2)所示化合物之量為350wtppm以下之有機EL材料用之鋁鉗合錯合物之製造方法，其特徵為，使異丙氧化鋁依序與喹啉酚衍生物及HO-Ar1 -Ar2 所示之酚性化合物反應以製造式(1)所示鋁鉗合錯合物之製造方法中，上述酚性化合物為由HO-Ar1 -X所示之化合物與(Ar2 )a -Y所示化合物反應所得者，且式(2)所示化合物之量為350wtppm以上之粗鋁鉗合錯合物經有機溶媒洗淨或再結晶後，經昇華精製將鹵化物之量精製至350wtppm以下之方法， (式(1)與式(2)中，Ar1 為2環之伸芳基，Ar2 為1至2環之芳基，Ar1 與Ar2 中所含芳香族環之合計數目為3至4環，該些芳香環可相互縮合；R1 至R6 各自獨立地表示氫或碳數1至8之烴基，X為鹵素；又上述HO-Ar1 -Ar2 、HO-Ar1 -X，及(Ar2 )a -Y中，Ar1 、Ar2 及X之內容係與上述為相同之內容；Y表示Cu、X、Li、B(OH)2 、MgX、ZnX、SnMe3 ，其中，X表示鹵素，a表示1~10之整數)。
  3. 如申請專利範圍第1項之有機EL材料用之鋁鉗合錯合物之製造方法，其中，酚性化合物為由HO-Ar1 -X所示 之化合物與(Ar2 )a -Y所示化合物反應所得之粗製酚性化合物，經再結晶使HO-Ar1 -X所示化合物之量為350wtppm以下所得之精製物。
  4. 如申請專利範圍第2項之有機EL材料用之鋁鉗合錯合物之製造方法，其中，酚性化合物為由HO-Ar1 -X所示之化合物與(Ar2 )a -Y所示化合物反應所得之粗製酚性化合物，經再結晶使HO-Ar1 -X所示化合物之量為350wtppm以下所得之精製物。
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US8263770B2 (en) 2012-09-11
JP4700494B2 (ja) 2011-06-15
KR101111542B1 (ko) 2012-02-15
CN1832924A (zh) 2006-09-13
JPWO2005014551A1 (ja) 2007-11-22
CN100462358C (zh) 2009-02-18
TW200508360A (en) 2005-03-01
US20100256377A1 (en) 2010-10-07
WO2005014551A1 (ja) 2005-02-17
KR20060036114A (ko) 2006-04-27
US20070054148A1 (en) 2007-03-08

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