TW593623B - Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds - Google Patents

Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds Download PDF

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TW593623B
TW593623B TW090115959A TW90115959A TW593623B TW 593623 B TW593623 B TW 593623B TW 090115959 A TW090115959 A TW 090115959A TW 90115959 A TW90115959 A TW 90115959A TW 593623 B TW593623 B TW 593623B
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Viacheslav A Petrov
Ying Wang
Vladimir Grushin
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Du Pont
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Description

玖、發明說明： 發明背i 發明領域 本發明關於具氟化苯基p比咬、苯基㈣及苯基峻琳之電發 光11*(111)錯σ物。也關於其中活性層包含一種電發光錯 合物之電子裝置。 ii關技術之
I 可發射光有機電子裝置，如構成顯示器之發光二極體係 存在於許多不同種類之電子設備中。在所有此類裝置中，有 機活性層係以三明治方式被夾在兩電接觸層之間。至少一層 電接觸層是透光的，因此光可穿過電子接觸層。#橫跨電接 觸層施加電壓時，有機活性層放出光穿過透光電接觸層。 使用有機電發光化合物作為發光二極體之活性成份是為人 所熱知的。簡單有機分子如蒽、雙二唑衍生物及香豆素係熟 知可表現出電發光。半導體共軛聚合物也曾被用於作為電發 光成份，如，例如Friend等人，美國專利5,247，190，iieeger 等人，美國專利5,4〇8，109及Nakano等人，已發佈的歐洲專利 申請案443 861中曾揭示過的。、羥基喳啉與三價金屬離子， 特別是銘的錯合物曾被廣泛地用於作為電發光成份，如，例 如Tang等人，美國專利5,552,678中曾揭示過的。
Burrows及Thompson曾發表/ac_參（2_苯基吡啶）銥可用於有 機發光裝置中作為活性成份（Appl. Phys· Lett. 1 999，75 4)。
O:\72\72026-921219. DOC 593623 當銥化合物存在於主導電材料中時，成效可達最大。 Thompson另外發表活性層是摻有知參！^_(4，，5、二氟苯基风 哫C，N]Ir(IIl)之聚（N-乙烯基咔唑）的裝置。
Preprints 2〇〇〇, 41(1)，770)。 但是’對具有較佳效率之電發光化合物持續有需求。 發明概述 本發明係關於一種具至少兩個2_苯基吡配位基之銥化合物 (一般相當梦”Ir(III)化合物”），其中配位基上有至少一個氟或 氟化基團。此銥化合物具有下列第一式：
IrL L L xL’yLnz (第一式） 其中： X = 〇或1，y=〇、1或2及z = 0或1，條件為： x=〇或 y+z=0及 當 Y=2 時，z=0 ; L’ =雙配位基或單配位基，而且非為苯基吡啶、苯基嘧 啶或苯基喳啉；條件為： 當L’是單配位基時，y + z = 2，及 當L’是雙配位基時，z=0 ; L -早配位基’而且非為冬基p比淀和苯基。密淀或苯基 4 p林；及
La、Lb&Le是彼此類似或相異，而且La、Lb及L。各具有
O:\72\72026-921219. DOC 下列結構式（I): 其中：
其中 n=l-6且 X=H、C1 或 ΒΓ，
CnF
RriU與Rs-Rs之相鄰對可社 Ri-R纟中至少一個係選自F、 及
合以形成五-或六-員環， 2n+1、0CnF2n+1 及 OCF2X A=C或N ’條件為當A==N時，無、。 在另一個具體實例中，本笋 Λ月係關於mer-2 -苯基p比淀、苯 基嘧啶及苯基喳啉取代之弈μ 貝化合物，從此化合物可製得上 列Ir(III)化合物。此先質化人 負1匕。物具有下列結構式（11)或（m):
其中入及1^8係如上結構⑴中所定義般，而且m
O:\72\72026-9212I9.DOC (III) 593623 其中： _ R10-R19 中至少一個係選自 F、CnF2n+i、〇CnF2n+a〇CF2X， 其中n=l-6且X=H、Cl或Br，而且r2〇是H。 已知苯基-吡啶、苯基-嘧啶及苯基^奎啉鍵可自由旋轉。但 疋，本文所討論的，將以單一方向描述此類化合物。 在另一個具體實例中，本發明係關於一種具有至少一層放 射層包含七列Ir(III)化合物，或上列Mm)化合物之組合之有 鲁 機電子裝置。 本文中，”化合物”一詞欲指由分子所構成的不帶電物質， 其中該分子進一步由無法藉物理方法分離之原子所組成。，， 配位基” 一詞欲指一種連接在金屬離子之配位層的分子、離子 或原子。”錯合物”一詞（當其用作名詞時），欲指具有至少— 個金屬離子及至少一個配位基之化合物。，，基團"一詞欲指化 合物的一部份，如有機化合物中的取代基或錯合物中的配位 _ 基。’’facial”一詞欲指具有八面體結構之錯合物“心匕的一種 兴構物，其中二個”a"基團全部相鄰，即，位於八面體中一面 的角落。"mendicmal，，欲指具有八面體結構之錯合物Ma3b^々
一種異構物，其中三個”a”基團佔據三個位置使兩兩間彼此呈 反式形態。”相鄰”一詞（當其用於表示有關裝置中的各層 時），不必要指一層緊臨另一層。另一方面，”相鄰尺基，，一詞 用於表示化學式中彼此相鄰之尺基（即原子上以鍵相連之R
O:\72\72026-921219.DOC -9- 593623 基）。光敏的丨’ 一詞表示任何g ;目+父 了王見电發光及/或光敏性之物質。 - 凰AH說明 圖1是發光裝置（LED)之概略圖。 圖2是LED測試裝置的概略圖。 之細節抵色 本發明之Ir(III)化合物具有如上之第一式 Ιγ(ΙΙΙ)Ι/Ι^\Ι^。
I 上列ΐι·(ιμ)化合物經常被歸於環金屬錯合物。具有下列第二 式之Ir(III)化合物也經常被歸於雙_環金屬錯合物： IrLaLbL^L^ (第二式） 其中= y z L、L、L及L”係如上列第一式中所定義者。 具有下列第二式之Ir(III)化合物也經常被歸於參-環金屬錯合 物： (第三式）
IrLaLbL 其中：
La、L及I/係如上述第一式中所定義者。 較好的環至屬錯合物是中性及非離子性的，而且可完整地 昇華。這些物質經由真空沈積所獲得的薄膜呈現良好至極佳 的電發光性質。將氟取代基導入銥原子上的配位基中可增加 錯合物的安定性及揮發性。結果，真空沈積可在較低溫度下 O:\72\72026-921219.DOC -10 - 593623 進行並且可避免錯合物的分解。將氟取代基導入配位基經常 可降低非輕射衰退速率及固態中自淬滅現象（self_qUenching effect)。這些降低量可使發光效率提高。改變具有推電子及 拉電子性質之取代基可細微調整化合物的電發光性質並因此 最佳化電發光裝置的亮度及效率。 然而不希望受理論所束縛，相信從銥化合物之發射係以配 位基為基礎，導因於金屬對配位基之電荷轉移。因此，可呈 現電發光今化合物包括這些上列第二式IrLaLbL、L，，z及上式 第三式IrLaLbLc之化合物，其中第三式中所有La、Lb&Lc是苯 基吡呢、苯基嘧啶或苯基喹啉。上列結構式⑴及之 基和結構（III)之R1(rRl9基可選自慣用有機化合物之取代基， 如烷基、烷氧基、_素、硝基及氰基，以及氟、氟化烷基及 氟化烷氧基。此基團可部份或完全被氟化（全氟化）。較好的 鍊化合物具有皆選自敦、全氟化垸基（CnF2n+1)及全氟化垸氧 基（〇CnF2n+1)tRl_R8及RiQ-Ri9取代基，其中全氟烷基及烷氧 基具有1-6個碳原子，或式ocFj之基團，其中χ==Η、ci或玢。 已發現田$基中任一個或多個是確基時，環金 屬錶錯合物之電發光性質較I。因&，較佳係R「RAiWRl9 基中無硝基。 含虱％可為咐咬環”密咬或林，較佳係至少—個氣化取 代基係位於含氮環上，最佳係cf3。
O:\72\72026-921219.DOC -11 - 593623 任何過渡金屬配位化學已知的慣用配位基適合作為L，及L，， 配位基。雙配位基實例包括具有兩個配位基之化合物，如伸 乙基二胺及乙醯基丙酮酸酯，其可被取代。單配位基實例包 括氯化物及硝酸根離子及單胺。較佳為該銥錯合物是中性且 可昇華。若使用單一個雙配位基，其淨電荷應為_丨。若使用 兩個單配位基，他們的組合淨電荷應為-1。雙_環金屬錯合物 可用於製備參-環金屬錯合物，其中配位基並非完全相同。
I 在一個轉佳具體實例中，銥化合物具有上述第三式 IrLaLbLc。 在一個更佳具體實例中，La=Lb=Lc。這些更好的化合物經 常呈現facial結構，如由單晶X-射線繞射所測得，其中配位在 银上之氮原子係與配位在银上之碳原子呈反式形態。這些較 好的化合物具有下列第四式： /ac-Ir(La)3 (第四式） 其中La具有上列結構式（I)。 化合物也可呈現meridional幾何，其中兩個配位在銀上的氮 原子係彼此呈反式。這些化合物具有下列第五式·· mer-Ir(La)3 (第五式） 其中La具有上列結構式（I) ° O:\72\72026.921219.DOC -12 - 593623 上列第四式及第五式之化合物實例係列於下面表1中。 表1 化合物 A Ri r2 Rs R4 Rs R6 Rt Rs 式 1-a C H H cf3 H H H H H 四 1-b C H H cf3 H H H F H 四 1-c C H H cf3 H F H H H 四 1-d C H H H H F H H H 四 1-e :c H H cf3 H H cf3 H H 四 1-f C H H H H H cf3 H H 四 i-g • C H H H H H H F H 四 1-h C Cl H cf3 H H H H H 四 1-i -t H H cf3 H H H 〇ch3 H 四 H C H H cf3 H H F H H 四 l-k c H H N〇2 H H cf3 H H 四 1-1 c H H cf3 H H H ocf3 H 四 1-m N — cf3 H H H H F H 四 i-q c H H cf3 H H och3 H H 四 1-r c H OCH, H H H H cf3 H 四 1-s c H H H H F H F H 四及五 1-t c H H cf3 H H F H F 五 1-u c H H cf3 H F H F H 五 1-v .c H H cf3 H H H F H 五 結 -w 上列第二式Ιι·Ι/Ι^υΑ”ζ之化合物實例包括各具有下列 構（IV)、（V)、（VI)、（IX)及（X)之化合物 I^il、1-〇、1-p、1 及 1 -X : O:\72\72026-921219.DOC -13 - 593623
O:\72\72026-921219.DOC -14-
593623 (X) 上列第三式IrLaLbLe之銥錯合物一般係由適當經取代2-苯 基吡啶、苯基嘧啶或苯基喳啉製得的。如上列結構（II)中所 示，此經取代2 _苯基ρ比淀、苯基p密淀及苯基峻淋係以良好至 極佳產量利用 0. Lohse，P.Thevenin，E. Waldvogel Synlett， 1999, 45-48中所描述之經取代2-氯吡啶、2-氯嘧啶或2-氯喳啉 與芳基硼酸進行蘇如奇（Suzuki)耦合所製得。此反應係以吡啶 衍生物進行說明，其中X及Y在下列式（I)中代表取代基：
具有上列結構（II)之2-苯基吡啶及2-苯基嘧啶化合物實例 作列於下面表2中。 2026-921219.DOC -15 - 593623
表2 化合物 A Ri R2 Rs R4 Rs Re r7 Rs R9 2-a C H H cf3 H F H H H H 2-b C H H cf3 H H cf3 H H H 2-c C H H N〇2 H H cf3 H H H 2-d Γ c H H cf3 H H F H H H 2-e r c H H cf3 H H H CH30 H H 2-f c Cl H CF3 H H H H H H 2-g c H H H ch3 H H F H H 2-h N — H H H H H F H H 2-i c H H cf3 H H H CF30 H H 2-j N — cf3 H H F H H H H 2-k C H H cf3 H H H F H H 2-1 r。 cf3 H H Γη~ H H H H H 2-m ,c Cl H cf3 H H H F H H 2-n c cf3 H H H H H F H H 2-0 ' c CF3 H H H H H CH30 H H 2-P c Cl H cf3 μ H H H CH30 H H 2-q 卜N — cf3 H 卜H H F H H 2-r c Cl H cf3 H H H H H F 2-s c H H cf3 H H H H H 2-t c Cl H H H F H H H H 2-v c H H cf3 H Γη CH30 H H H 2-w c H CH30 H H H H cf3 H H 2-x c H H H H H F F H H 2-y c H H cf3 H H F H F H 2-z c H H cf3 H F H F H H 2-3,3. c H H Br H H H Br H H
一個具有上列結構（III)之經取代的2-苯基喹啉化合物實例
是化合物 Μ，其中R17=CF3、R1〇-Rl6&Ri8_R2〇=H。 因此所製得之2-苯基吡啶、嘧啶及喹啉可用於環金屬銥錯 -合物之合成。已利用商業可取得之三氯化銥水合物及三氟醋 酸銀發展出一種便利的單步驟方法。此反應一般係以過量的 2-苯基峨淀”密咬或㈣，無溶劑，在3當量Ag〇c〇cF3的存 在下芫成。此2-苯基吡啶的反應係說明於下列式（？）中：
O:\72\72026-921219.DOC -16- 593623 Y-
IrCb, AgOCQCF^ X- r<^N'
190-195°C :Ir (2) X一一
N 參-環金屬銥錯合物被分離、純化並以元素分析、lH&Op nmr 光瑨數據及對於化合物U、&&&以單晶χ-射線繞射完整 表示其特薇。在某些例子中，獲得異構物之混合物。將常可 使用此混合物而不需分離出各個異構物。 具有上列第二式IrLaLbL’yL’’z之銥化合物，在某些例子中可 利用如製備這些具有上列第三式IrLaLbLC之銥化合物相同的 合成程序自反應混合物中分離。此錯合物也可藉首先製備具 有下列結構VII之銥二聚物中間物製得： bL\ CL dL /If、 Ϊ )\I/ B—〇 〇IB \ \ 一lr
\1/ (VII 其中： B=H、CH3或 C2H5，且
La、Lb、Le及Ld可相同或彼此相異，而且La、ρ 1/及1^可各具有上列結構（I)。 O:\72\72026-921219.DOC -17- 銀二臂私 物一般可藉先反應三氯化銥水合物與2-苯基吡啶、苯 基密％或苯基喳啉並加入Na〇B而製得。 種特別有用的銥二聚物是具有下列結構νπι之羥基銥二 聚物，
此中間物可藉乙醯醋酸乙基酯之添加用於製備化合物h。 本發明也關於一種電子裝置，其包含至少一層位於兩電接 觸層間的光敏層，其中裝置之至少一層包含本發明銥錯合 物。裝置經常具有額外的電洞傳遞及電子傳遞層。典型結構 係表不於圖1中。裝置100具有陽極層110及陰極層150。與陽 極相鄰是一層含有電洞傳遞物質之層120。與陰極相鄰是一層 έ有電子傳遞物質之層140。介於電洞傳遞層與電子傳遞層之 間的是光敏層130。 視裝置100的用途而定，光敏層13〇可為一種可被施加電壓 (如在發光二極體或發光電發光電池中）所活化之發光層，一 層對輻射能有應答且可在有或無施加偏壓下（如在光偵測器 中）產生訊號之物質。光偵測器實例包括光導電電池、光敏電 O:\72\72026-921219.DOC -18 - 593623 阻器、光控繼電器、光電晶體及光電管和光伏打電池，如這 些 Markus，John，電子與核子字典，47〇 及 476 (McGraw_Hiii 公司1966)中所描述之名詞。 本發明銥化合物特別可用於作為層130中光敏材料，或作為 層140中電子傳遞物質。本發明銥錯合物最好用於作為二極體 中的發光材料。在這些應用中曾發現本發明氟化化合物不需 存在於固體基質稀釋射以使其發揮效用。以該層總重量為 基準，一層含有大於20重量％至高達1〇〇重量％之銥化合物的 物質可祕作為發射層。與非氟化鍊化合物相反，發現當參 (2-苯基吡啶）Ir(III)在發射層中的存在量只有6_8重量％時可 達到最大效率。降低自淬減作用是必要的。額外的物質可存 在於σ銥化合物之發射層中。例如，螢光染料可存在於其中 以改又發光顏色。也可加入稀釋劑。稀釋劑可為聚合體物質， 如聚（Ν-乙埽基叶唾）及聚梦垸。其也可能是小分子，如 4,4 -Ν，Ν 咔唑二苯基或三級芳族胺。當使用稀釋劑時，銥 化合物的存在量一般不大，以該層總重量為基準，通常低於 2 0重量％ ’較佳係低於1 〇重量％。 在某些例子中，銥錯合物可能以超過一種異構物形式存 在’或者可能存在著不同錯合物之混合物。須了解在上面 OLED的时論中’欲以”銥化合物，’涵蓋化合物及，或異構物之 混合物。
O:\72\72026-921219.DOC -19- 593623 為了獲得高效率LED，電洞傳遞物質之h〇m〇(最高填入分 子軌道）應與陽極的工作函數成一直線，電子傳遞物質之 LUMO (最低未填入分子軌道）應與陰極的工作函數成一直 線。物質的化學互容性與昇華溫度在選擇電子與電洞傳遞物 質上也是重要考量。 0LED中其他層可由任何已知可用於該等層中之物質製 成。陽極1.10是一種對逐出正電荷載體特別有效率的電極。其 可能是由々例如含有金屬、混合金屬、合金、金屬氧化物或 · 混合金屬氧化物之物質所製成的，或者其可為導電聚合物。 適合的金屬包括族Η金屬，族4、5及6中之金屬和族8_1〇之過 渡金屬。若陰極是為透光的，一般可使用族12、13及14金屬 之混合金屬氧化物，如銦-錫氧化物。整個文章係使用 命名系統，其中週期表之各族從左至右被命名為丨_18 (CRC 化學及物理手冊，81版，2000)。陽極11〇也可包含有機物質 如聚苯胺，如”從可溶導電聚合物製得之撓曲發光二極體,，， · 自然，357卷，477-479頁（1992年6月11日）中所描述般。陽極 與陰極中至少一個應至少部份透光使所產生的光可被見到。 層120之電洞傳遞物質實例已被概述於，例如γ· Wang著 Kirk-Othmer化學技術百科全書，第4版，第18卷，837-86〇頁， 1996中。可使用電洞傳遞分子及聚合物。普遍使用的電洞傳 遞分子是：N，N’-二苯基-N，N，-雙（3-甲基苯基Hu，·二苯 O:\72\72026-921219.DOC -20- 593623 基]-4,4’-二胺（TPD)、1，1-雙[(二-4-甲苯基胺基）苯基]環己燒 (TAPC)、N，N’-雙（4-甲基苯基）-N，N，-雙（4-乙基苯 基）-[1，1’-(3,3’-二甲基）二苯基]-4,4，-二胺斤丁？0)、肆-(3_甲基 苯基）-N，N，N’，Nf-2,5-伸苯基二胺（PDA)、a-苯基-4-N，N-二苯 基胺基苯乙烯（TPS)、對-(二乙基胺基）_苯甲醛二苯基腙 (DEH)、三苯基胺（TPA)、雙[4-(N，N-二乙基胺基）-2-甲基苯 基](4-甲辱苯基）甲烷（MPMP)、1-苯基-3-[對-(二乙基胺基）苯 乙烯'基]-5^[對-(二乙基胺基）苯基]7比吐琳（PPR或deASP)、 1，2-反-雙（911-咔唑-9-基）環丁烷（0€2：6)、1^^，，>^肆（4-甲基 -苯基二苯基）-4,4’-二胺（TTB)及卟啉化合物，如酞花青 銅。常用的電洞傳遞聚合物是聚乙烯基咔唑、（苯基甲基）聚 矽烷及聚苯胺。藉掺入電洞傳遞分子，如上述，這些分子於 聚合物（如聚苯乙烯及聚碳酸酯）中也可獲得電洞傳遞聚合 物。 層140之電子傳遞物質實例包括鉗有金屬之似8_羥基喹啉 化合物，如參（8-羥基喳啉）鋁（Alq3);啡啉基質化合物，如2,9-二甲基_4,7-二苯基-l，l〇-啡啉（DDPA)或4,7-二苯基-1，10-啡 啉（DPA)及唑化合物如2-(4-二苯基）-5-(4-第三丁基苯 基）-1，3,4-呤二唑（？3〇)及3-(4-聯苯基）-4-苯基-5-(4-第三丁基 苯基）-1，2,4-三唑（TAZ)。層140可幫助電子傳遞，也可作為緩 衝層或限制層以防止激發子在層界面處淬滅。最好此層可促
O:\72\72026-921219.DOC 進電子移動並降低激發子淬滅。 陰極150是一種對逐出電子或負電荷載體特別有效率的電 極。此陰極可為任何工作函數比陽才亟低之金屬或非金屬。陰 極的材料可選自族i (如Ll、Cs)之驗金屬、族2(驗幻金屬、 族12金屬，包括稀土元素及鑭系元素和婀系元素。可使用材 料如鋁、銦、鈣、鋇、彭及鎂以及組合物。含U有機金屬合 物也可被声覆在有機層與陰極層之間，以降低操作電壓。 已知有機私子裝置中具有其他層。例如，導電聚合物層1 與活性層130之間可能有一層（未顯示出），用以幫助正電荷傳 遞及/或各層的帶-間隙配合，或作為保護層。相同地，活性 層130與陰極層150之間可能有額外層（未顯示出），用以幫助 負私荷傳遞及/或各層間帶-間隙的配合，或作為保護層。可 使用技術上已知的各層。而且，任何上述層可由兩或多層所 組成。或者，部份或所有無機陽極層11〇、導電聚合物層i2Q、 活性層130及陰極層150可經表面處理以增加電荷載體傳遞效 率。各成份層之材料的選擇，最好係權衡提供裝置高元件效 率之目標來決定。 已了解各功能層可由超過一層所構成的。 此裝置可依序藉蒸汽沈積各層於適合基材上而製得。可使 用如玻璃及聚合物膜之基材。可使用慣用蒸汽沈積技術，如 熱洛發、化學蒸汽沈積及類似物。或者，此有機層可由溶於 O:\72\72026-92I219.DOC -22- 593623 週當溶劑之溶液或分散液，利用任何慣用塗覆技術塗覆而成 的。一般而言，不同層將具有下列範圍之厚度：陽極ιι〇, 500-5_埃，較佳係1()()()_2_埃；電洞傳遞層12〇, 埃’較佳係200-800埃；發光層130, 1(M〇〇〇埃，較佳係⑽__ 埃；電子傳遞層140, 50-1000埃，較佳係2〇〇_8〇〇埃；陰極15〇， 20(M__，較佳係·麵埃。裝置中電子_電洞結合區 的位置及裝置的放射光譜可能受各層的相對厚度所影響。因 此’電子傳:遞層的厚度應經選擇，以使電子_電洞結合區落在 發光層。理想的層厚比例將視所用材料的實際性質而定。 已了解以本發明銥化合物所製成之裝置的效率，可進一步 藉取佳化裝置中其他層加以改善。例如，可使用較有效率的 陰極如Ca Ba或LiF °也可應用可使操作電壓降低或增加量 子效率之成形基材及新穎電洞傳遞物質。也可加入額外層以 修改不同層之能級並幫助電發光。 本發明鎮錯合物經常是磷光及光致發光，而且可用於異於 OLED的應用中。例如’録之有機金屬錯合物已被用於作為對 氧敏感的指示劑、在生物分析中作為磷光指示劑及作為觸 媒。二環金屬錯合物可用於合成參環金屬錯合物，其中第三 個配位基是相同或不同的。 實例 J說明一些本發明特徵及優點。他們意在說明本發
O:\72\72026-92I2I9.DOC -23 - 593623 明，但不欲限制之。所有百分比皆以重量為基準，除非另外 指示。 實例1 此實例說明用於形成銥化合物之2_苯基(2及2-苯基嘧啶 的製備。 ^ 所用的一般程序係描述於〇. L〇hse，p . Thevenin5 &
Waldv〇gelSynlett，1999,45_48中。在典型實驗中，迴流加熱 ，如以㈣^升除氣過的水⑶克碳酸却叫別毫升以-二甲氧基乙燒、〇.5克Pd(PPh3)4、〇〇5莫耳經取代2'氯峨银 4或喊旬及0.05莫耳經取代苯基㈣所形成之混合…㈣ I寺、300毛升水稀釋所得反應混合物並以CH2C12 (2χ1〇〇 毫升）萃取之。以Mgs04乾燥合併的有機層並藉由真空除去溶 劑。藉真:空分_化液體產物。㈣產物從己料再处曰出 來。分離出的物質純度-般>98%。起始物、產率、新物:之 溶點及潍點係列於表3中。疆數據及分析數據係列於表4 中 〇
O:\72\72026-921219.DOC -24- 593623 表3 2 -苯基口比淀、苯基口密淀及苯基口奎口林之製備 化合物_產率0/〇_彿點/毫米汞柱（熔點rc 2-s 70 2-a 72 2-b 48 2-u 75 2-c 41 2-d 38 2-e 55 2-g 86 2-t 65 2-k 50 2-m 80 2-f 22 2-v 63 2-w 72 2-x 35 2-y 62 2-z 42 2-aa 60 (76-78) (95-96) (39-40) 74.5/0.1 71- 73/0.07 77-78/0.046 (38-40) 72- 73/0.01 52-33/0.12 95-96/13 61-62/0.095 (68-70) 66-67/0.06 (58-60)
O:\72\72026-921219.DOC -25- 593623 表4 2 -苯基ρ比淀、苯基口密淀及苯基口奎ρ林之4生質 化合物 ]H NMR 分析％， 19F NMR 發現（計算） 或 MS (M+) 2-s 7·48(3Η)， -62.68 C，64.50 7·70(1Η)， (64.57) 7.83(1H)， Η，3·49 7·90(2Η)， (3.59) I 8.75(1H) Ν，6·07 (6.28) 2-a 7·19(1Η)， -60.82(3F，s)， C，59.56 7·30(1Η)， -116.96(lF，m) (59.75) 7.43(1Η)， Η，3·19 7·98(2Η)， (2.90) 8.07(1Η) Ν，5·52 9.00(1Η) (5.81) 2-b 7·58(1Η)， -62.75(3F，s)， C.53.68 7·66(1Η)， -63.10(3F，s) (53.60) 7·88(1Η)， Η，2·61 8.03(1Η)， (2.40) 8.23(1Η)， Ν，4.53 8.35(1Η) (4.81) 8·99(1Η) 2-u 7·55(1Η)， -62.89(s) C，69.17 7·63(1Η)， (70.33) 7·75(2Η)， Η，3·79 7·89(2Η)， (3.66) 8.28(2Η)， Ν，4·88 O:\72\72026-921219.DOC -26-
593623 表4 (繼續） 化合物 NMR 分析％，發現（計算） 19F NMR 或 MS (M+) 8·38(1Η)， (5.12) 8.50(1H) 2-c 7·53(1Η)， -62.14(s) C,53.83(53.73) i 7.64(1H)， Η，2·89 7.90(1H)， (2.61) 8·18(1Η)， Ν，9·99 8·30(1Η)， (10.44) 8·53(1Η)， 9·43(1Η) 2-d 7·06(1Η)， -62.78(3F，s)， C，59.73 7·48(1Η)， -112.61 (59.75) 7·81(3Η)， Η，2·86 8·01(1Η)， (lF，m) (2.90) 8.95(1Η) Ν，5·70 (5.81) 2-e 3.80(3Η) -62.63 C，61.66 6·93(2Η)， (s) (61.90) 7·68(1Η)， Η，3·95 7·85(1Η)， (4.04) 7.96(2Η)， Ν，5·53
O:\72\72026-921219.DOC -27- 593623 表4 (繼續） 分析％，發現（計算） 化合物 !h nmr 19f nmr 或 MS (M+) 8·82(1Η)， (5.38) 2-g 2.70(3H) -114.03 C，76.56 7.10(3H)， ㈣ (77.00) 7·48(1Η)， Η，5·12 - ^ 7.60(1H)， (5.30) 8.05(2H)， Ν，5·43 (7.50) 2-1 7.10(2H)? -62.73 C，50.51 7.35(2H)， (3F，s) (52.17) 7·96(1Η)， -113.67 Η，1·97 8·78(1Η)， (lF，m) (2.17) Ν，5·09 (5.07) 2-k 7·08(2Η)， -62.75 C，60.39 7.62(1H)， (3F，s) (59·75)，Η，3·38 7·90(3Η)， -111.49 (2.90), 8·80(1Η)， (m) N，5.53 (5.51) 2-m 7·10(2Η)， -62.63 C，52.13 7·80(2Η)， (3F，s) (52.17)
O:\72\72026-921219.DOC - 28 - 593623 表4 (繼續） 分析％，發現（計算） 化合物 lU NMR 19F NMR 或 MS (M+) 8·00(1Η)， -1 1 1.24 H，2.16 8.75(1Η)， (m) (2.17) N，4.85 Ϊ (5.07) 2-f - ^ 7·55(3Η)， -62.57(s) 257(M+， 7·77(2Η)， C12H7F3C1N+)， 8·06(1Η)， 222(M-C1) 8.87(1Η) 2-v 3·8(3Η)， -62.70ppm C，61.66(61.37)， 6·95(1Η)， H，3.98(3.67)， 7·30(1Η)， Ν，5·53(5.48) 7·50(1Η)， 7·58(1Η)， 7·75(1Η)， 7·90(1Η)， 8.87(1Η) 2-w 8.54(lH，d)， -63.08(3F，s) 8.21(2H，d)， 7.70(2H，d)， 7.24(lH，s)，
O:\72\72026-921219.DOC -29- 593623 表4 (繼續） 分析％，發現（計算） 化合物 b NMR_19F NMR_或 MS (M+) 2-x 6.82(lH，dd)， 3.91(3H?s) 6.9(2H，m)， -109.70(lF，m)， , 7.18(2H，m)， -1 13.35(lF，m)· 2-y 7.68(2H，m)， 7.95(lH，m)， 8.65(lH，m); 6·94(1Η)， -62.72(3F，s)， 7·62(2Η), -109.11(2F，m) 2-z 7.82(1H)， 8·03(1Η)， 8.96(1H); 6·85(1Η)， -62.80(3F，s)， 6·93(1Η)， -107.65(lF，m)， 7.80,7.90， -112.45(lF，m)· 2-aa 8.05(3Η)， 8.89(1H); 7.70(3H，m)， 7.85(3H，m)， 7.80,7.90, 8.85(lH，m).
O:\72\72026-921219.DOC -30- 實例2 此貝例說明上列第四式/ac-Ir(La)3之銥化合物的製備。 在典型實驗中，在A中18(M95°C (油浴）下徹底攪拌lrCl3 · nH2〇 (53-55% Ir)、AgOCOCF3 (3.1 當量/lr)、2-芳基吡啶（過 里）及（選用的）少量水所形成之混合物約2_8小時。以CH2cl2 锨底萃取所得混合物直到萃取液是無色的。此萃取液經矽石 笞柱過濾以產生透明黃色溶液。蒸發此溶液獲得一殘留物， 以甲醇處禹之以產生參環金屬Ir錯合物之有色晶體。藉過濾 分離出此錯合物，以甲醇清洗之，在真空下乾燥並（視情況） 藉結晶作用、真空昇華或索格利特（soxhlet)萃取純化之。產 率：10-82%。以NMR光譜數據及元素分析表示所有物質之特 徵，並將結果表示於下面表5中。獲得該系列三種錯合物之單 晶X-射線結構。 化合物1 -b 在A氣流中隨溫度緩慢地（3〇分鐘）增加至185它（油浴），徹 底攪拌 IrCl3 · nH20 (54% Ιι· ; 508毫克）、2-(4-氟苯基）-5-三氟 甲基说呢’化合物kk (2.20克）、Ag〇COCF3 (1.01克）及水所形 成之混合物。在185-190°C下2小時之後，混合物固化。將混 合物冷卻至▲溫。以二氯甲燒萃取此固體直到萃取液脫色。 合併的一氯甲坑溶液經短石夕石管柱過濾並蒸發之。將甲醇（5〇 毫升）加入殘留物中之後，將燒瓶保持在·1〇〇c下放置隔夜。 O:\72\72026-921219. DOC •31 - 593623 刀離出參-環金屬錯合物，化合物b之黃色沈殿，以甲醇清洗 4並在真空下乾燥之。產量：1·〇7克（82%)。藉於丨，2-二氯乙 烷中緩慢冷卻其溫熱溶液可獲得該錯合物之X-射線品質的晶 體。 化合物1 - e 在N2氣流中隨溫度緩慢地（15分鐘）增加至192它（油浴），徹 底攪拌 Ii*Cl3 · nH2〇 (54% II*·，504毫克）、2-(3-三氟甲基苯基）-5-二氟甲基啤哫，化合物bb (1.6〇克）及Ag〇COCF3 (1.01克）所形 成之混合物。在190-195°C下6小時之後，混合物固化。將混 合物冷卻至室溫。將此固體置於矽石管柱上，然後以大量二 氣甲烷清洗之。濾液蒸發後以甲醇處理殘留物以產生黃色固 體。收集固體並在25毫升微-索格利特（s〇xhlet)萃取器中以二 氣甲燒萃取之以純化之。分離出參-環金屬錯合物，化合物e 之黃色沈澱，以甲醇清洗之並在真空下乾燥之。產量：〇· 5 9 克（39%)。從熱1，2-二氯乙烷中獲得該錯合物之χ-射線品質的 晶體。 化合物1 -d 在A氣流中190-195°C(油浴）下徹底攪拌IrCl3 · nH2〇 (54% Ir，508笔克）、2-(2-乳苯基）-5-三氟甲基吡啶，化合物aa (丨53 克）及AgOCOCFs (1.01克）所形成之混合物約6小時15分鐘。將 混合物冷卻至室溫’然後以熱1，2-二氯乙烷萃取之。此萃取 O:\72\72026-921219.DOC -32- 液經短石夕石管柱過濾並蒸發之。以甲醇（20毫升）處理殘留 物 &成所需產物，化合物d沈殿，過滤分離之’以甲醇清洗 之並在真空下乾燥之。產量：0.63克（49%)。從二氯甲烷/甲 醇中獲得該錯合物之X-射線品質的晶體。 化合物p 在乂氣流中190-195t：(油浴）下徹底攪拌IrCh · nH2〇 (54%
Ir ; 503毫克）、2-(心三氟甲氧基苯基三氟甲基吡啶，化合 物ee (2.00克）及Ag〇c〇CF3 (1·1〇克）所形成之混合物約2小時 45分鐘。將混合物冷卻至室溫，然後以二氯甲烷萃取之。此 萃取液經短矽石管柱過濾並蒸發之。以甲醇（20毫升）處理殘 留物’造成所需產物，化合物i沈澱，過濾分離之，以甲醇清 洗之並在真空下乾燥之。產量：〇86克。另外，藉蒸發母液 並添加石油醚至殘留物可獲得〇.27克錯合物。總產量：113 克（72%)。 4匕合物1 - q 在N2氣流中隨溫度緩丨更地（3 〇分鐘）增加至1 85。〇(油浴），徹 底授拌IrCl3 · nH20 (54%Ir ; 530毫克）、2-(3_甲氧基苯基）_5· 二氟甲基吡啶（2.50克）、八8〇(：〇€?3(1.12克）及水（1毫升）所形 成之混合物。在185°C下1小時之後，混合物固化。將混合物 冷卻至室溫。以二氯甲烷萃取此固體直到萃取液脫色為止。 合併的二氯甲烷溶液經短矽石管柱過濾並蒸發之。以己烷清 O:\72\72026-921219.DOC -33- 593623 洗殘留物，然後從丨，2-二氯乙烷-己烷再結晶（兩次）。產量： 0.30 克。BF NMR (CD2C12，20°C)，δ : -63 (s)。1H NMR (CD2Cl2, 2〇°C )，5 : 8·1 (1Η)，7.9 (1Η)，7.8 (1Η)，7.4 (1Η)， 6·6 (2H) ’ 4·8 (3H)。從1，2-二氯乙烷-己烷中可獲得該錯合物 (1，2-二氯乙燒，己烷溶劑化物）之X-射線品質的晶體。此面心 錯合物是橘色-光致發光。 相同地，製得化合物hk、1-f至1-h、丄」:丄至1-mii-r 〇 在化合物UL的製備中，獲得氟在心或〜位置之異構物的混合 物。
_____ 表 5 化合物 1-a 分析C計鼻發現） _ NMR (CD2C12，25〇C) H N Cl 2.5 (2.7) 4.9 (4.9) [：0.0 (0.2) lH: 6.8 (1H), 6.9 (1H), 7.0 (1H), 7.8 (2H), 7.95 (1H)? 8.1 (1H) 9F:-63.4 1-b C H N 47.4 (473) ^ 2.0(2.1) 4.6 (4.4) XU: 6.4 (1H), 6.75 (1H), 7.7 (1H), 7.8 (1H), 7.95 (1H)? 8.05 (1H) 19F: -63.4 (s); -109.5 (ddd) 1-c C H N 47.4 2.0 (2.0) 4.6 (4.5) 1ΐί: 6.6 (1H), 6.7 (1H), 6.9 (1H), 7.8 (1H), 8.0 (1H), 8.6 (1H) 19F: -63.5 (s);-112.8 (ddd) 1-d C H N 55.9 (561^ J 3.0(3.2) 5.9(5.8) lH: 6.6 (2H), 6.8 (1H), 7.0 (1H), 7.6 (1H), 7.7 (1H), 8.4 (1H) 19F:-115.0 (ddd) 1-e C H N 14.11433Γ ' 1.7(2.1) 3.9(3.6) 6.9 (1H), 7.1 (1H), 7.8 (1H), 8.0 (2H), 8.2 (1H) 19F: -63.0 (IF), -63.4 (IF) 1-f C H N 50.4 (563)^〜' 2.5 (2.7) 4.9 (4.9) !H: 6.9 (1H), 7.1 (2H), 7.6 (1H), 7.8 (1H), 7.9 (1H), 8.1 (1H) l9F: -62.4 O:\72\72026-921219.DOC -34- 593623 表5 (繼續） 化合物 分析（計算發現） NMR (CD2C12，25〇C) l-g C: 55.9 (56.3) H: 3.0 (3.2) N: 5.9 (6.0) 乜 6.4 (1H), 6.7 (1H)，7.0 (1H), 7·6 (1H)，7·7 ΡΗ)，7·9 (1Η) 19F:-112.6 (ddd) 1-h C: 51.0 (45.2) H: 2.1 (2.3) N: 4.9 (4.2) !Η: 6.8 (1H)5 6.95 (1H), 7.05 (1H), 7.7 (1H), 8.0 (1H), 8.9 (1H) 19F:-63.3 1-i C: 49.4 (49.3) Η: 2·9 P.8) N: 4.4 (4.4) 3·6 (3H)，6.3 (1H)，6.6 (1H)，7.7 (2H)，7.85 (1H)，7.95 (1H) 19F: -63.2 Η C： 47.4 (47.4) H: 2.0 (2.3) N: 4.6 (4.7) lR: 6.7 (m), 7.1 (m)? 7.5 (m)5 7.6 (m), 7.7 (m)? 8.0 (m), 8.2 (m) 19F: 8 s 共振(-63.0- -63.6)及 8 ddd 共振(-92.2- -125.5) l-k C: 43,5 (44.0) H: 1.8(2.1) N: 8.5 («.4) lH: 6.9 (1H)? 7.15 (1H)5 8.1 (1H)? 8.3 (1H), 8.45 (1H), 8.6 (1H) 19F: -62.9 1-1 C: 42.2(42.1) H: 16(1.8) N: 3.8 (3.7) lH: 6.5 (1H), 6.7 (1H), 7.75 (1H), 7.85 (1H), 8.0 (1H), 8.1 (1H) 19F: -58.1 (IF), -63.4 (IF)
實例3 此實例說明上列第二式IrLaLbLcxL，yL"z之銥錯合物的製備。 \ 彳匕合物1 -η 在 190-195°〇下激烈攪拌11*(：13.11112〇(54%11*;510毫克）、 2-(3-三氟甲基苯基）喹啉（υο克）及三氟醋酸銀（11()克）所形 成之混合物約4小時。所得固體在矽石上以二氯甲烷進行色層 分析以形成二環金屬錯合物與未反應配位基之混合物。後者 可以溫己燒藉萃取混合物而將其除去。萃取液變無色後，收 集不溶於己烷之固體並在真空下乾燥之。產量為〇·29克。 NMR : -63·5 (s，6F)，-76·5 (s，3F)。藉單晶X射線繞射研究可 建立此錯合物之結構。 O:\72\72026-921219.DOC -35- 593623 化合物1 - o^ 在 190°C 下攪拌 IrCl3 · nH2〇（54% Ir ; 500毫克）、2_(2-氟苯 基）-3-氣-5-三氟甲基吡啶（2·22克）、水（0·3毫升）及三氟醋酸銀 (1 ·00克）所形成之混合物約1 ·5小時。在矽石上以二氯甲燒色 層分析此固體以產生0.33克二環金屬水三氟乙酸根，化合物 1-Ρ與未反應配位基之2:1共結晶加成物。19f NMR : -63.0 (9F)，-76·5 (3F) ’ -87.7 (2F)，-114.4 (1F)。藉從二氯甲燒_ 己^元再〜吨可除去共結晶之苯基ρ比淀配位基。藉單晶X射線 繞射研咒可建立此加成物及錯合物之結構。 實例4 此實例說明具有上列結構（VIII)之羥基銥二聚物的製備。
IrCl3· nH2〇(54%Ir; 510毫克）、2_(心氟苯基）巧_三氟〒基 吡啶（725毫克）、水（5毫升）與乙氧基乙醇（2〇毫升）所形成之 混合物在迴流加熱下激烈攪拌4·5小時。加入Na〇H(23克）溶 於水（5¾升）所形成之溶液後，接著加入2〇毫升的水，此混合 物在迴流加熱下攪拌2小時。將混合物冷卻至室溫，以5〇毫升 的水稀釋之並過遽之。此固體與3G毫升^二氯乙垸及水性 NaOH (2.2克溶於8毫升的水中）在迴流加熱下激烈攪掉— 時。從混合物中蒸掉有機溶劑，留下橘色固體於水相所形成 《懸/于液。過遽分離橘色固豸，以水徹底清洗之並在真空下 乾燥< 以產生〇·94克（95%)的銥羥基二聚物（光譜純的）。巾
O:\72\72026-9212I9.DOC -36- 593623 NMR (CD2C12) : -1.0 (s，1H，Ir0H)，5·5 (dd，2H)，6.6 (dt， 2H)，7.7 (dd，2H)，7.9 (dd，2H)，8 〇 (d，2H)，9_1 (d，2H)。 19F NMR (CD2C12) · -62.5 (s，3F)，〇 (ddd，IF)。 列5 此實例說明從银一聚物製備雙環金屬錯合物。 化合物1 -p 獲自貫例4之銥#至基二聚物（丨⑼毫克）、乙臨醋酸乙基酯 ί (〇·〇75毫升J 4倍過量）及二氯甲烷（4毫升）所形成之混合物在 i«溫下隔夜攪拌。此溶液經短碎石管柱過濾、並蒸發之並獲得 橘黃色固體，以己烷清洗之並乾燥之。此錯合物的產量是1〇9 毫克（94%)。bNMRCCDAl,): 3.9(dm，CH2)， 4·8 (s，CH3COCH)，5·9 (m)，6.7 (m)，7·7 (m)，8·0 (m)，8·8 ⑷。19F NMR (CD2C12) : _63·1 (s，3F)，-63.2 (s，3F)，-109.1 (ddd，IF) ’ -109.5 (ddd)。分析：計算：c，44.9 ; Η，2.6 ; N， 3.5。發現：c，44.4 ; H，2.6 ; N，3.3。 化合物1 - w
以50¾克三氟醋酸處理獲自實例4之羥基銥二聚物（〇2〇克） /合於THF (6晕升）所形成之溶液，經短矽石管拄過濾，蒸發之 計算量〇·5毫升，以己烷（8毫升）處理之並隔夜靜置。分離出黃 色固體結晶，以己烷清洗之並在真空下乾燥之。產量（1:1 THF /合戶,Η匕物）· 0.24克（96%)。19F NMR (CD2C12, 20°C )，（5 : -63·2
〇：\72\72026-921219 DOC -37- (S，3F)，.76.4 (s，3F) ’ -107 3 (ddd，1F)。1H NMR (CD2C12, 20 C )’ δ : 9.2 (br s，lH)，8.2 (dd，1H)，8·1 (d，1H)，7.7 (m，1H)， 6.7 (m，1H)，5.8 (dd，1H)，3·7 (m，2H，THF)，1.8 (m，2H， THF) 〇 化合物1 一x 在A氣中i5(M55t下攪拌三氟醋酸根中間物，化合物卜界 (75毫克）丨與2-(4_溴苯基）_5_溴吡啶（13〇毫克）所形成之混合 物約30分奠。將所得固體冷卻至室溫並將其溶於ch2ci2中。 所得溶液經矽膠過濾並蒸發之。以溫己烷清洗殘留物數次並 在真空下乾燥之以剩下黃色、黃色光致發光固體。產量·· 74 毫克（86%)。19F NMR (CD2C12, 20。〇, 5 : -63·1 (s，3F)，-63.3 (s，3F)，-1〇8·8 (ddd，IF)，-109.1 (ddd，IF)。4 NMR (CD2C12, 20°C )，（5 : 8.2(s)，7.9 (m)，7.7 (m)，7·0 (d)，6.7 (m)，6.2 (dd)，6.0 (dd)。如X-射線分析所確認，此錯合物是經線的， 其氟化配位基之氮呈反式形態。 實例6 此實例說明上列第五式mer-Ir(La)3之銥化合物的製備。 化合物1-s 此錯合物係依類似化合物1 ·η之方式合成之。根據NMR、 TLC及TGA數據，結果是近1:1之面心與經線異構物的混合 物0 O:\72\72026-921219. DOC -38- 化合物1 _t 在N2氣流中隨溫度緩慢地（30-40分鐘）增加至i65t (油 浴），激烈攪拌 IrCl3 · nH20 (54% Ir ; 〇·4〇克）、2-(3,5-二氟苯 基）-5-三氟甲基吡啶（1·40克）、Ag〇COCF3 (〇·81克）及水（0·5 毫升）所形成之混合物。在165 °C下40分鐘之後，混合物固化。 將混合物冷卻至室溫。以二氯甲燒萃取此固體直到萃取液脫 色為止。合併的二氯甲烷溶液經短矽石管柱過遽並蒸發之。 * 以己烷徹扈清洗殘留物並在真空下乾燥之。產量：〇 53克 (49%)。19F NMR (CD2C12, 20。(：），6 : -63.55 (s，3F)，-63.57 (s5 3F)’ -63.67 (s，3F)，-89·1 (t，IF)，-100.6 (t，IF)，-102.8 (dd， IF)，-118.6 (ddd，IF)，-119.3 (ddd，IF)，-123.3 (ddd，IF)。 4 NMR (CD2C12, 20。。），ά : 8·4 (s)，u (m)，7·9 ㈣，7.6 (s) ’ 7.5 (m)，6.6 (m)，6.4 (m)。也如藉x-射線分析所確認， 此錯合物是經線的。 化合物1 -u 此錯合物依類似化合物1 _q之方法製備並分離之，然後藉結 晶作用從1，2-二氯乙烷-己烷純化之。純化過之產物的產率為 53%。此錯合物是經的，如依照nmr數據。19FNMR(CD2C12, 2(TC )，5 : -63.48 (s，3F)，-63.52 (s，6F)，-105.5 (ddd，IF)， -105.9 (ddd，IF)，-106.1 (ddd，IF)，_1〇7·4 (t，IF)，_1〇7·9 (t， IF)，]〇9·3 (t，lF)。4 NMR (CD2C12, 20°C )，5 : 8.6 (m)， O:\72\72026-921219. DOC -39- 593623 8.3 (s)，8.2 (s) ’ 8·ι (m)，7.9 (m)，7.6 (m)，6·6 (m)，6.4 (m)， 6.0 (m)，5.8 (m)。 化合物1 -v 此mer-錯合物係依類似化合物丨_w之方法，利用三氟醋酸根 二環金屬中間物，化合物1-x，與2-(4-氟苯基）-5-三氟甲基吡 淀製得。19F NMR (CD2C12, 20°C )，5 : -63.3 0 (s，3F)，-63.34 (s，3F)，-63.37 (s，3F)，-108.9 (ddd，IF)，-109.0 (ddd，IF)， -1〇9·7 (ddd) IF)。^ NMR (CD2C12, 20°C )，5 ·· 8.3-7.6 (m)， 6·7 (m)’ 6·6 (dd)，6.3 (dd)，6·0 (dd)。當在 1 大氣壓下昇華時， 此發黃光之mer-錯合物異構化成發綠光的面心異構物，化合 物 1 -b。 實例7 此實例說明利用本發明銥錯合物形成OLED。 包含電洞傳遞層（HT)、電發光層（EL層）及至少一層電子傳 遞層（ET)之薄膜OLED裝置可藉熱蒸發技術製得。使用一種具 有油擴散幫浦之Edward Auto 306蒸發器。所有薄膜沈積之基 本真空度係在1(T6 torr範圍内。沈積槽可沈積五種不同的薄膜 而不需要破壞真空度。 使用塗有氧化銦錫（ITO)之玻璃基材，其具有約1〇〇〇_2〇⑻ 埃之IT0層。先以1NHC1溶液蝕刻掉不要的IT〇區域以式樣化 此基材以形成第一種電極圖案。使用聚亞胺帶作為屏蔽。然 O:\72\72026-9212I9.DOC -40- 593623 後在水性清潔劑溶 材。然後以蒸餾水 汽中脫脂〜3小時。 液中以超曰波方式清理已式樣化的1丁〇基 ，接著以異汚醇清洗基材，然後在甲苯蒸 然後將乾淨、已式_ _6 水、 基材放入真空槽中並將該槽 由土 10 ωπ·。然後另外利用氧電漿清理基材约㈣分鐘。清 理後，然後依序藉熱蒸發將多層薄膜沈積在基材上。最後， 透過屏蔽沈積A1之式樣化金屬電極。沈積過程中利用石英晶 體監測器咖。n STC_2GG)測量該膜厚度。實例中所描述之所 有膜厚係假設所沈積物質的密度41時定額算得的。然後將已 完成的〇咖裝置取出真空槽並立刻特徵化之而無封裝。 裝置各層及厚度之摘要係表示於表6中。在所有例子中，陽 極如上所討論般是IT〇，陰極是厚度在7〇〇_76〇埃範圍之Μ。 在部份樣品中，使用兩層電子傳遞層H係指相鄰队層 所塗覆之層。 O:\72\72026-921219.DOC -41 - 593623 表6 Alq3=參(8-羥基喳啉)鋁 〇〇卩八=2,9-二甲基-4,7-二苯基-1，10-啡啉 Ir(ppy)3 =/此-參(2-苯基p比淀)缺 MPMP =雙「4-ίΝ,Ν胃二乙基胺基)-2-甲基苯基](4-甲基苯基)甲烷 樣品 ΗΤ層（厚度，埃） EL層（厚度，埃） ET層（厚度，埃） 對照 MPMP (528) Ir(ppy)3 (408) DDPA(106)+Alq3 (320) 1 ΜΡΜΡ (520) 化合物life (499) DDPA(125)+Alq3 (365) 2 ΜΡΜΡ (541) 化合物1士（580) DDPA(407) 3 ΜΡΜΡ (540) 化合物U (499) DDPA(112)+Alq3 (340) 4 ΜΡΜΡ (525) 化合物1土 (406) DDPA(106)+Alq3 (341) 5 ΜΡΜΡ (570) 化合物lil (441) DDPA(107)+Alq3(339) 6 ΜΡΜΡ (545) 化合物id (462) DDPA(111)+Alq3 (319) 7 ΜΡΜΡ (643) 化合物lzg(4〇9) DDPA(112)+Alq3 (361) 8 ΜΡΜΡ (539) 化合物M(43〇) DDPA(109)+Alq3 (318) 9 ΜΡΜΡ (547) 化合物(412) DDPA(105)+Alq3 (300) 10 ΜΡΜΡ (532) 化合物1土 (457) DDPA(108)+Alq3 (306) 11 ΜΡΜΡ (603) 化合物Μ (415) DDPA(111)+Alq3 (303) 12 ΜΡΜΡ (551) 化合物(465) DDPA(106)+Alq3 (313) 13 ΜΡΜΡ (520) 化合物lzl(4〇5) DDPA(410) 14 ΜΡΜΡ (504) 化合物Μ (400) DDPA(393) 15 ΜΡΜΡ (518) 化合物(153) DDPA(418) 16 ΜΡΜΡ (556) 化合物1-m (416) DDPA(430) 17 ΜΡΜΡ (520) 化合物l-n(419) DDPA(420) 18 ΜΡΜΡ (511) 化合物13(412) DDPA(413) 19 ΜΡΜΡ (527) 化合物1iE(425) DDPA(412) 20 ΜΡΜΡ (504) 化合物iza(417) DPA(407) 21 ΜΡΜΡ (525) 化合物id (419) DPA(416) 22 ΜΡΜΡ (520) 化合物1^(421) DPA(405)
OLED樣品可藉測量其（1)電流-電位（I-V)曲線，（2)電發光輻 射隨電壓變化，及（3)電發光光譜隨電壓變化。所用裝置200 是表示於圖2。以Keithley源-測量單元型號237、280測量OLED 樣品220之I-V曲線。以Minolta LS-110發光計210測量電發光 輻射（單位為Cd/平方米）隨電壓之變化，同時利用Keithley SMU掃描電壓。電發光光譜係利用一對鏡片230經由電子光閘 O:\72\72026-921219. DOC -42- 593623 240分散穿過光譜儀250,然後以二極體列偵測器260測量之而 獲得。所有三種測量係同時完成並利用電腦270控制之。在特 定電壓下裝置的效率可藉LED的電發光輻射除以使裝置運作 所需電流密度測得。單位為Cd/安培。 結果係表示於下面表7 : 表7 銥化合物之電致發光性1 樣品 最大輻射， Cd/平方米 最大輻射時的效率， Cd/安培 最大效率， Cd/安培 近最大波長， 毫微米 對照 在22伏特下540 0.39 0.48 522 1 在2玉伏特下1400 3.4 11 525 2 在25伏特下1900 5.9 13 525 3 在18伏特下830 1.7 13.5 525 4 在27伏特下7.6 0.005 0.13 521 5 在25伏特下175 0.27 1.8 530, 563 6 在20伏特下514 1.5 2.2 560 7 在26伏特下800 0.57 1.9 514 8 在28伏特下1200 0.61 2 517 9 在18伏特下400 1.1 4 545 10 在16伏特下190 2.3 3.3 575 11 在25伏特下1150 1.2 3.8 506, 526 12 在20伏特下340 0.49 2.1 525 13 在21伏特下400 3 5 520 14 1900 5 9 525 15 2500 6 11 525 16 在27伏特下100 0.17 0.2 560 17 在28伏特下3.5 0.005 0.014 575 18 在26伏特下30 0.08 0.16 590 19 在21伏特下2000 6 8 532 20 在26伏特下350 0.60 1.6 595 21 在22伏特下1200 5 545 22 在19伏特下80 1 540 最大效率是裝置中電發光化合物之值的最佳指標。其提 供一種必須將多少電子輸入裝置以獲得特定輸出光子（輻 射）值之測量。其基本上是一個重要的值，其反應發光物質 之本質效率。其對實際應用也是重要的，因為較高的效率 O:\72\72026-921219.DOC -43 - 思、指需要較少兩 萑 耗。效率較高 、&得相同輻射量，因此指較少電力消 的射出泰子、由、裝置也易具有較長的壽命，因為較大部分 學心：轉變成光子，取代產生熱或造成不想要的化 心大邵分本發明銥錯合物具有遠高於起源介^參 人冬基吡哫）銥錯合物之最大效率。這些具有較低效率之錯 口物發現也有上述作為磷光或光致發光物質或作為觸媒之 效用。
O:\72\72026-921219.DOC -44-

Claims (1)

  1. 拾、申請專利範園： 1 · 一種包含— 個發射層之有機電子裝置，其中至少20重量 %之發射層包含至少 IrLaLbLcxL，yL，，z : 含至少一種具有下式之化合物： L’yL”z， 其中： P0或1，y=〇、！或2及z==0或1，其條件為： x：=〇 或 y+z=0及 ^ 當 7=2 時，z=0 ; L· 種雙配位基或一種單配位基，而且非為苯基 吡啶、苯基嘧啶或苯基喳啉；其條件為： 當L’是一種單配位基時，y+z=2，及 當L’是一種雙配位基時，z=〇 ; L’’ = 一種單配位基，且非為苯基吡啶和苯基嘧啶或 苯基峻P林；及 La、1^及1/係彼此類似或相異，而且La、Lb及Lc各 具有下列結構式（I):
    其中： O:\72\72026-921219.DOC 汉！土 R4與汉5至Rs之相鄰對可結合以形成一個五或 六員環； R^Rs 中至少一個係選自 F、CnF2n+1、〇CnF2n+a 〇〇2Χ，其中n=：1_6且Χ==Η、叫汾；及 A=C或Ν，其條件為當Α=Ν時，心不存在。 根據申請專利範圍第丨項之裝置，其中χ=ι、丫=〇及2=〇。 3 根據申凊專利範圍第2項之裝置，其中a=c而且心至!^ 中無係選自硝基。 ， 4_根據申請專利範圍第1項之裝置，其中R3>cf3。 根據申請專利範圍第4項之裝置，其中R5至118中至少一 個係選自 F、CnF2n+i、〇CnF2n+1 及 〇CF2X，其中 n=l_6且 Χ==Η、Cl或 Br。 6 •根據申請專利範圍第2項之裝置，其中A=C，r3 = cf3， R7==F而且 R1、R2、R4至 R6及 118為11。 7 •根據申請專利範圍第2項之裝置，其中A=C，r3及 R6 = CF3，而且Rl、R2、R4、r5、RaR^h。 8·根據申請專利範圍第2項之裝置，其中A=C，r3==cf3， 汉6及汉8外而且Ri、R2、R4、Rs及r7 = h。 9·根據申請專利範圍第1項之裝置，其中Χ = 〇及y=1時具有 —個下列結構（VI): O:\72\72026-921219.DOC 593623
    10. 一種包含一個發射層之有機電子裝置，其中該發射層包
    含一種稀釋劑及低於20重量％之至少一種具有下式之 化合物： IrLaLbLc， 其中： L、L及Lc係彼此類似或相異，而且La、^及厂各 具有下列結構式（I):
    其中： 1至IU與R5至Rs之相鄰對可結合形成一個五或六 員環，· 仏至118中至少一個係選自F、CnF2n+i、〇CnF2n+i及 OCF2X，其中 n=l-6且 X=H、Cl或 ΒΓ ;及 O:\72\72026-92I219.DOC 11.593623 A=C或N，其條件為當A=N時，心不存在。 根據申請專利範圍第i 0項之裝置，其中該稀釋劑係選自 聚（N-乙烯基咔唑）、聚矽烷、4,4，_n，n，-二咔唑二苯基及 三級芳族胺。 12. 根據申請專利範圍第丨項之裝置，另外包含一個電洞傳 遞層，其係選自N，N，-二苯基-N，N，-雙（3-甲基苯基）n — 二苯基]-4,4’·二胺（τργ))、；^!-雙[(二_心甲苯基胺基）苯基] 環己$(TAPC)、N，N’-雙（4-甲基苯基）·ν，Ν，_雙（4-乙基苯： # 基）_[1，1’-(3,3’-二甲基）二苯基]_4,4，-二胺（ETPD)、肆-(3- 甲基苯基）->1，；^，>^，>1’-2,5-伸苯基二胺（？〇八）、-苯基 -4-Ν，Ν-二苯基胺基苯乙缔（TPS)、對二乙基胺基）_苯甲 酸二苯基腙（DEH)、三苯基胺（TPA)、雙[4-(Ν，Ν·二乙基 胺基）-2-甲基苯基](4-甲基苯基）甲烷（ΜΡΜΡ)、1-苯基 -3-[對-(二乙基胺基）苯乙烯基][對_(二乙基胺基）苯 基]咐p坐啉（PPR或DEASP)、1，2-反-雙（9H-吟唑-9-基）環 % 丁烷（DCZB)、N，N，N，，N，-肆（4-甲基-苯基）-(1，1，-二苯 基）-4,4’-二胺（TTB)、外琳化合物及其組合。 13. 根據申請專利範圍第1項之裝置，其另外包含一個電子 傳遞層，其係選自參（8-羥基喹啉）鋁、2,9-二甲基-4,7-二苯基-1，10-啡啉（DDPA)、4,7-二苯基-l，l〇-啡啉 (DPA)、2-(4-二苯基）-5-(4-第三丁 基苯基）-1，3,4_崎二唑 O:\72\72026-921219.DOC -4- 14. (?80)、3-(4-聯苯基）-4-苯基-5-(4-第三丁基苯基）-1，2,4-三口坐（TAZ)及其組合。 一種化合物，其具有選自/flc七(L)3 (第四式）、七(l)3 (第五式）及其組合〈化學式，其中L係選自如下所示族 X^至群，並且具有一種下面結構⑴：
    Rs (I)
    O.\72\72026-9212\9.DOC 593623 1^至114與115至R8之相鄰對可結合形成一個五或六 員環； 1至尺8中至少一個係選自F、CnF2n+1、〇CnF2n+1及 OCF2X，其中 n=l-6且 X=H、Cl或 Br ;及 A=C或N，條件為當A=N時，1不存在。 15. —種化合物，其具有一種選自下面結構（IV)、（V)、（VI)、 (IX)及（X)之結構：
    (IV)
    (V)
    O:\72\72026-921219.DOC -6- 593623
    (ix)
    O:\72\72026-921219.DOC 16. 16.593623 一種包含一個發射層之有機電子裝置，其中該發射層包 含一種選自下列⑴與（ii)之化合物： ⑴一種具有選自/^-Ir(L)3 (第四式）、ma-Ir(L)3 (第五式）及其組合之化學式的化合物，其中L係選自如 下所示族JLi至Ιζπι及Ι-q至1-v之群，並且具有下面纟士構 ⑴：
    O:\72\72026-921219.DOC 593623 1至尺4與115至R8之相鄰對可結合形成一個五或六 員環； RiSRs中至少一個係選自F、CnF2n+1、〇CnF2n+1及 〇CF2X，其中 n=l-6且 X=H、Cl或 Br ;及 A=C或N，條件為當A=N時，心不存在；以及 (ii) 一種具有一種選自下面（IV)、（V)、（VI)、（IX) 及（X)之結構的化合物：
    (IV)
    (V)
    O:\72\72026-921219.DOC -9- 593623 O:\72\72026-921219.DOC
    (IX)
    -10- 593623 17. 根據申請專利範圍第16項之裝置，其中該發射層另外包 含一種稀釋劑。 18. 根據申請專利範圍第17項之裝置，其中該稀釋劑係選自 聚（N-乙烯基咔唑）、聚矽烷、4,4'N，N’-二咔唑二苯基及 三級芳族胺。 1 9. 一種選自如下所示化合物2-a至2-aa之化合物，其具有下 面結構（II):
    R3 ⑻
    R7
    化合物 A Ri r2 r3 R4 Rs R6 Rt Rs r9 2-a C H H cf3 H F H H H H 2-b C H H cf3 H H cf3 H H H 2-c C H H N〇2 H H cf3 H H H 2-d C H H cf3 H H F H H H 2-e C H H cf3 H H H ch3o H H 2-f C Cl H CF3 H H H H H H 2-g C H H H ch3 H H F H H 2-h N -- H H H H H F H H 2-i C H H cf3 H H H cf3o H H 2-j N — cf3 H H F H H H H 2-k C H H cf3 H H H F H H 2-1 C cf3 H H H H H H H H 2-m c Cl H cf3 H H H F H H 2-n c cf3 H H H H H F H H 2-0 c cf3 H H H H H ch3o H H 2-p c Cl H cf3 H H H ch3o H H 2-q N -- cf3 H H H H F H H 2-r c Cl H cf3 H H H H H F 2-s c H H cf3 H H H H H H 2-t c Cl H H H F H H H H 2-v c H H cf3 H H ch3o H H H 2-w c H ch3〇 H H H H cf3 H H 2-x c H H H H H F F H H 2-y c H H cf3 H H F H F H 2-z c H H cf3 H F H F H H 2-aa c H H Br H H H Br H H O:\72\72026-921219.DOC -11 - 593623 其中：R9是Η ; , 1至R4與R5至R8之相鄰對可結合形成一個五或六 員環； 1至以8中至少一個係選自F、CnF2n + 1、OCnF2n+1及 OCF2X，其中 n=l_6且 X=H、Cl或 Br ;及 A=C或N，條件為當A=N時，1不存在。 20. 一種具有下面結構（III)之化合物，
    其中 Rl7 = CF3 且 Rio 至 Ri6 及 Rl8 至 。 21. —種具有下面結構VII之化合物， CL dL /ΙΓ\ ΒΙΟ\ /Ο—Β \ \bA 1 其中： B=H、CH3 或 C2H5 ;且 La、Lb、Le及Ld可相同或彼此相異，而且 O:\72\72026-921219.DOC -12- 593623 La、Lb、Le&Ld各具有下列結構（I):
    其中： 1至R4與化至R8之相鄰對可結合形成一個五或六 員環； 1至118中至少一個係選自F、CnF2n+1、OCnF2n+1& OCF2X，其中 n=l-6且 X=H、Cl或 Br ;及 A=C或N，條件為當A=N時，；^不存在。 22.根據申請專利範圍第21項之化合物，其中： La=Lb=Lc=Ld ； B=H ; R3 = CF3 ； R7=F ;及 Ri、R2、R4至 R6及 R8=H。 O:\72\72026-921219.DOC -13-
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