TW200300790A - Electroluminescent platinum compounds and devices made with such compounds - Google Patents
Electroluminescent platinum compounds and devices made with such compounds Download PDFInfo
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Description
200300790 ⑴ 5¾、發明說明 (ί明說明應敘明··發明所屬之技術領域、先前技術、内容、實施方式及圖式簡單說明) 發明背景 枯術領域 本發明係關於鉑(11)之電發光錯合物’其具有橫越可見 光光譜之發射光譜。其亦關於其中活性層包括電發光 Pt(II)錯合物之電子裝置。 先前技術 發射光之有機電子裝置’如組成顯示器之發光二極管, 存在於許多不同種類之電子設備。在所有之此種裝置,有 機發光層夾在兩個電接觸層之間。至少一個電接觸層為透 光使得光可通過電接觸層。在橫越電接觸層施加電力時, 有機層發射通過透光電接觸層之光。 已知在發光二極管中使用有機電發光化合物作為活性 成分。已知如蒽、噻二唑衍生物、及薰草素之簡單有機分 子顯示電發光。亦已使用半導體共軛聚合物作為電發光成 分,例如,如Friend等人之美國專利5,247,19〇、等人之 美國專利5,408,109、與Nakano等人之公告歐洲專利申請案443 861所揭示。具有三價金屬離子(特別是鋁)之訌經基膣寧基 已廣泛地作為電發光成分,例如,如Tang等人之美國專利 5,552,678所揭示。 具有摻雜#有機金屬錯合物之聚合物之發光層之電發 光裝置已由Burrows與Thompson揭示於公告之pcT申請案w〇 00/57676 。 然而,對於發射橫越可見光譜之光夕古〜&人仏 %之有效電發光化合物 200300790
仍有持續之需求。 發明内容 本發明係關於一種具有式I或式II之金屬錯合物:
Ptl^L2 (I)
PtLlL3L4 (II) 其中: 在式I中: L2為單陰離子性雙牙配位基; 在式II中: L3為單牙配位基;及 L4為單牙膦配位基; 在式I與II中: L1選自圖1所示之式III,及圖2所示之式VII,其中: 在式III與VII中: E1至E4在各情形為相同或不同,而且為CR2或N; R2在各情形為相同或不同,而且選自H、D' Cn(H+F)2n+1、F 、OCn(H+F)2n+1、OCF2Y、SR3、與N(R3)2,或相鄰 R2基可結合形 成5-或6-員環; R3為 Η、CnH2n+1; Y為Η、Cl、或Br; η為1至12之整數; 在式III中: A為N或SR3; R1在各情形為相同或不同,而且選自D、Cn(H+F)2n+1、F、 OCn(H+F)2n+i、OCF2Y、SR3、與N(R3)2,或相鄰 R2 基可結合形成 200300790 (3) _ι_βι 5 -或6 -員環, α為0、1或2;及 在式VII中: R4至R7在各情形為相同或不同,而且選自H、D、Cn(H+F)2n+1 、F、OCn(H+F)2n+l、OCF2Y、SR3、與N(R3)2,或相鄰 R2 基可結合 形成5 -或6-貝壞。 在另一個具體實施例中,本發明係關於具有至少一個活
性層(其包含以上金屬錯合物或以上金屬錯合物之組合) 之有機電子裝置。
在此使用之名詞’’化合物'’意圖表示由分子(其更包括原 子)組成之未帶電物質,其中原子無法藉物理方法分離。 名詞π配位基”意圖表示連接金屬離子配位球體之分子、離 子、或原子。字母nL”用以表示由中性母體化合物nHLf’因 損失氫離子而形成之具有公稱(-1)電荷之配位基。術語” 錯合物”在作名詞使用時,意圖表示具有至少一個金屬離 子及至少一個配位基之化合物。名詞π β-二羰基’’意圖表示 其中存在兩個以CHR基分離之酮基之中性化合物。名詞” β-烯醇基’’意圖表示β-二羰基之陰離子形式,其中已摘除 來自兩個羰基間之CHR基之Η。名詞”基”意圖表示一部份 化合物,如有機化合物中之取代基或錯合物中之配位基。 片語π相鄰”在指裝置中之層時,不必然地表示一層緊鄰另 一層。另一方面,片語π相鄰R基”用以指彼此在化學式中 緊鄰之R基(即,在藉鍵結合之原子上之R基)。名詞π光活 性’’指呈現電發光及/或光敏性之任何材料。此外,全部使 200300790 (4) ii»i 用IUPAC編號系統,其中週期表之族由左自右邊編為1至18 (CRC Handbook of Chemistry and Physics,第 81 版,2000)。在式及 方程式中,字母A、E、L、R、Q、Y、與Z用以表示其内 定義之原子或基。所有其他字母用以表示習知原子符號。 名詞11 (H+F)n意圖表示氫與氟之所有組合,包括完全氫化、 部份氫化或全氟化取代基。"發射最大值”表示得到最大電 發光強度之波長奈米。電發光通常在二極管結構中測量, 其中測試之材料夾在兩個電接觸層之間且施加電壓。光強 度及波長各可藉,例如,光電二極管與光譜儀測量。 圖式說明 圖1顯示本發明金屬錯合物中配位基L1之式III至VII。 圖2顯示本發明金屬錯合物中配位基L1之式VII至X。 圖3顯示用於本發明之召-烯醇基配位基之式XI與膦基 烷氧化物之式XII。 圖4顯示合成用於本發明之母體配位基化合物HL1之方 程式(1)。 圖5顯示用於本發明之l 3配位基之式。 圖6A與6B顯示用於本發明之L4配位基之式。 圖7顯示形成用於本發明之式I錯合物之方程式(2)與(3)。 圖8顯示形成用於本發明之式Π錯合物之方糕式(4)。 圖9為發光裝置(LED)之略示圖。 圖10為LED測試裝置之略示圖。 實施方式 本發明之金屬錯合物具有上示式I或式II,而且稱為環 -9- 200300790 I發明說明讀頁, 金屬化錯合物。鉑為+ 2氧化狀態且為四配位。式I之錯合 物為具有額外單陰離子性雙牙配位基L2之環金屬化錯合 物。式II之錯合物為具有兩個額外單牙配位基L3與L4之環 金屬化錯合物。較佳環金屬化錯合物為中性及非離子性, 而且可完整地昇華。經真空沉積得到之這些材料之薄膜呈 現良好至優良之電發光性質。 本發明之錯合物具有最大值範圍為藍色區域至紅色區 域之發光光譜。發光之顏色可藉由選擇適當配位基而調整 ,如以下所討論。 圖1所示具有式III之配位基L1衍生自其中噻吩基(在A 為S時)或吼咯基(在A為NR3時)鍵結至具有至少一個氮之 6 -員環之母體化合物。較佳為α為0。在A為NR3時,較佳 為R3為CH3。 在所有之E均為CR2,及R2基為不結合形成環之個別取 代基時,配位基衍生自噻吩基一及吡咯基一吡啶母體化合 物。較佳為吼咬環上有至少一個氛或含敗取代基,更佳為 在E1與E3位置。較佳之含氟取代基為F與CF3。 其他型式之具有式III之一般結構之配位基具有喹寧或 異喹寧基取代吡啶,如圖1之式IV至VI所示。圖1所示具 有式IV之配位基L1衍生自噻吩基一或吡咯基一喹寧母體 化合物。圖1所示具有式V或式VI之配位基L 1衍生自噻吩 基一或吼咯基一異喹寧母體化合物。在這些圖中,δ為1 或1至4之整數,R1、α與Α如以上式III所定義。較佳為喹 寧或異膣寧環上之至少一個取代基選自D、Cn(F)2n+1、F、 200300790 ⑹ I發明說明續頁 〇cn(F)糾、與ocf2y。 圖2所示具有式VII之配位基L 1衍生自其中苯基鍵結至 具有至少一個氮之6 -員環之母體化合物。 在所有之E均為C R2,及R2基為不結合形成環之個別取 代基時,配位基衍生自苯基一吡啶母體化合物。較佳為配 位基上有至少一個氘或含氟取代基,更佳為在E1與E3位置 。較佳之含氟取代基為F與CF3。 其他型式之具有式VII之一般結構之配位基具有膣寧或 異喹寧基取代吡啶,如圖2之式VIII至X所示。圖2所示具 有式VIII之配位基L1衍生自苯基一膣寧母體化合物。圖2 所示具有式IX或式X之配位基L1衍生自苯基一異產寧母 體化合物。在這些圖中,δ為0或1至4之整數,及R1與α如 以上式III所定義,及R4至R7如以上式VII所定義。較佳為 配位基上之至少一個取代基選自D、Cn(F)2n+1、F、OCn(F)2n+1 、與 OCF2Y 〇 母體配位基化合物HL 1通常可藉對應氣化雜環芳基與 有機侧酸或有機鎂試劑之標準16催化Suzuki或Kumada交叉 偶合製備,例如,如 〇· Lohse、P. Thevenin、E. Waldvogel之Synlett, 1999, 45-48所述。對於苯基一異喹寧,此反應描述於圖4之 方程式(1 ),其中R與R’表示取代基。部份或全氘化配位基 母體化合物通常可使用氘化成分藉相同之偶合法製備。氘 化成分經常為商業可得,或可藉已知合成方法製備。— L2配位基為單陰離子性雙牙配位基。通常這些配位基具 有N、Ο、P、或S作為配位原子,而且在對鉑配位時形成 200300790 (7) 發明說明續頁 5 -或6-員環。適合之配位基包括胺基、亞胺基、醯胺基、 烷氧化物、羧酸基、膦基、硫醇基等。這些配位基之適合 母體化合物之實例包括β-二羰基(β-烯醇基配位基),及其 Ν與S同系物;胺基羧酸(胺基羧酸基配位基);吡啶羧酸( 亞胺基羧酸基配位基);柳酸衍生物(柳酸基配位基);羥 基堕寧(羥基膣寧基配位基)與其S同系物;及二芳基膦基 烷氧化物(二芳基膦基烷氧化物配位基)。
β-烯醇基配位基通常具有圖3所示之式XI,其中R8在各 情形為相同或不同。R8基可為氫、鹵素、經取代或未取代 烷基、芳基、烷芳基、或雜環基。相鄰R8基可結合形成五 一與六一員環,其可經取代。較佳之R8基選自Η、F、 Cn(H+F)2n+i、-C6H5、-C4H3S、與-C4H30,其中 η為 1 至 12 之整數, 較佳為1至6。 適合之β -烯醇基配位基包括下列化合物。β -烯醇基形式 之簡寫在以下以括號表示。
2,4 -戊二 _ 基[acac] 1,3-二苯基-1,3-丙二綱基[01] 2,2,6,6-四甲基-3,5-庚二酮基[丁“^1] 4,4,4-三氟-1-(2_噻吩基)-1,3-丁二酮基[丁丁?八] 7,7-二甲基-1,1,1,2,2,3,3-七氟-4,6-辛二酮基[卩00] 1,1,1,3,5,5,5-七氟-2,4-戊二酮基|^7&。3(:] 1,1,1,5,5,5-六氟-2,4-戊二酮基|^63〇&(:] — 1-苯基-3-甲基-4-異丁基吡唑啉基[FMBP] β-二羰基母體化合物通常為商業可得。母體化合物 -12- (8)200300790
1,1,1,3,5,5,5-七氟-2,4 全氟戊烤-2與氨之反應 製備。此化合物應在無 水解。 戊二 _ cf3c(o)cfhc(o)cf3 可基於 ’繼而水解步驟,使用二步驟合成 水條件下儲存及反應,因為其易於 羥基喹寧基配位基可瘦‘ ^ 、士如烷基或烷氧基之基取代,其 部份或全氟化。適合之羥其 6 暴邊争基配位基之實例包括( 寫提供於括號中): 8-經基璧寧基[8hq]
2_甲基-8-經基膣寧基[Me-8hq] 10-羥基苯并膣寧基[10_hbq] 母體經基膣寧化合物通常為商業可得。 膦基烷氧化物配位基通常具有圖3所示之式χπ,其中 R在各I#形為相同或不同,而且選自Cn(H + F)2⑴與 C6(H + F)5, 、 R15在各情形為相同或不同,而且選自1^與Cn(H+F)h+i,及 0為2或3。
適合之膦基烷氧化物配位基之實例包括(簡寫提供於括 號中): 3-(二苯基膦基)_1_氧基丙烷[dpp〇] 、 1,1-雙(三氟甲基)·2·(二苯基膦基)_乙氧化物[tfmdpe〇] 一些母體膦基烷醇化合物為商業可得,或可使用已知步 顿製備’例如,對於tfmdpeO,如Inorg. Chem. 1985,第24卷,第 3680頁所報告之步驟。 L3配位基為單牙配位基。較佳為此配位基為單陰離子性 -13- 200300790
。此配位基可具有〇或s作為配位原子,與如烧氧化物、 敌酸基、硫羧酸基、二硫魏酸基、續酸基、硫醇基、胺甲 酸基、二硫胺甲酸基、硫卡腙陰離子、磺醯胺陰離子等之 配位基。在某些情形,如β -烯醇基之配位基可作為單牙配 位基。L3配位基亦可為配位陰離子,如鹵化物、确酸基、 硫酸基、六鹵銻酸基等。適合之L3配位基之實例示於圖5。 L3配位基通常為商業可得。
L4配位基為單牙膦配位基。較佳為,此配位基為非離子 性。膦配位基可具有式XIII PAr3 (XIII) 其中Αι:表示芳基或雜芳基。Ar基可為未取代或經烷基、 雜烷基、芳基、雜芳基、齒化物、羧基、颯基、或胺基取 代。適合之L4配位基之實例示於圖6A與6B,其中在圖6A 之式 6-3、6-8、6-8 及圖 6B 之式 6-13、6-16、6-17、6-18、6-19 、與6-21中使用”Men表示甲基。L4膦配位基通常為商業可得。
式I與II之錯合物之發光顏色主要由配位基L1、L2、L3、與 L4之選擇決定。通常,在L1具有式III時,顏色偏向較長波 長(’’偏紅”)。在L1具有式VII時,顏色偏向較短波長(”偏藍 π)。在配位基之含氮環具有至少一個經具有非鍵結7Γ電子 之雜原子(最佳為氧)鍵結之取代基、或至少一個可給予σ 電子之取代基(如烷基,較佳為甲基)時,此錯合物亦偏藍 。然而,這些通則亦發生例外。 錯合物之發光效率可藉由使用其中一些或全部之氫已 被氘取代之L 1配位基而改良。 -14- 200300790 (ίο) 發明說明續頁 式I之錯合物通常藉由首先形成橋接氣二聚物而由金屬 氣鹽製備。對於噻吩一吡啶配位基,此反應描述於圖7所 示之方程式(2)。然後藉由將母體配位基化合物之鹽(如 N a L2)加入橋接氯二聚物而形成式I之錯合物。此反應在圖 7之方程式(3)中使用β-烯醇基配位基之鈉鹽描述。母體配 位基化合物之鹽可藉任何習知方法製備,如藉由在惰性溶 劑中將氫化納加入HL2。
本發明具有式I之金屬錯合物之實例示於以下表1。在各 情形,α與δ為零。 表1
錯合物 L1式 A 取代基 L2 1-a III n-ch3 E1=E3 = E4 = CH e1=ccf3 acac 1-b IX • 無 acac 1-c IX - R6=t-butyl acac 1-d IX - R5=OCH3 acac 1-e IX - r6=cf3 acac 1-f IX - R6=F acac 1-g VII 鱗 El=E2=E4=CH e3=cch3 r5=cf3 r7=cf, TMH 1-h VII - ei=e3=E4=CH e2=coch3 r5=cf3 tfmdpeO -15- 200300790 (11)
1-i VII E1=E3 = E4 = CH e2=coch3 r4=f r6=f TMH i-j VII E1=E2 = E4 = CH e3=cch3 R4=F r6=f tfmdpeO 1-k VII ** Ei=E3=E4=ch e2=coc(ch3)3 R4=F r6=f TMH 1-1 VII ei=E2=E4=ch e3=cch3 R4=F r6=f TMH 1-m VII - ei=E2=:E4=;ch e3=cch3 r5=cf3 TMH
式II之錯合物亦通常藉由形成橋接氯二聚物而製備。然 後將其他兩種配位基加入此二聚物。較佳為,L3為單陰離
子性且如銀鹽A g L3而加入。L4如中性配位基,或在陰離 子性配位基之情形如NaL4之鹽而加入。對於具有苯基一 吡啶配位基之橋接氣二聚物,較佳反應描述於圖8所示之 方程式(4)。 _ 在L1選自以下表2之配位基之一,L3選自圖5所示之配位 基,及L4選自圖6A與6B所示之配位基之處,製備具有式II 之錯合物之組合庫。 -16 - 200300790 (12) 麵_腳 表2 配位基 L1式 A a 取代基 2-a III s 0 Ei=E2 二 E4=CH e3=ccf3 2-b III n-ch3 0 ei=E2=E4=ch E3=CCF, 2-c VII 麵 - Ei=e3=E4=CH e2=coch3 R5=CF, 2-d VII - - El=E2=E4=CH e3=coch3 r5=cf3 2-e VII - - E1=E3=E4 = CH e2=cch3 R4=F R6=F 2-f VII - - El=E3=E4=CH e2=coch3 R4=F r6=f
大部份具有配位基2-a或2-b之錯合物具有紅至紅一橙 色發光。大部份具有配位基2-c、2-d、2-e、或2-f之錯合 物具有藍或藍一綠色發光。 · 電子裝置 本發明亦關於包含至少一個置於兩個電接觸層間之光 活性層之電子裝置,其中裝置之至少一個光活性層包括本 發明之錯合物。如圖9所示,典型裝置100具有陽極層110 與陰極層1 5 0,及在陽極1 1 0與陰極1 5 0間之電活性層1 20 、1 3 0及視情況之1 4 0。相鄰陽極為電洞注射/運輸層1 2 0 。相鄰陰極為包含電子運輸材料之選用層1 4 0。電洞注射/ 運輸層1 2 0與陰極(或選用電子運輸層)間為光活性層1 3 0 -17- 200300790 (13) I發明說明續頁 。層120、130、與140個別地及概括地稱為活性層。 視裝置100之應用而定’光活性層130可為藉施加電壓活 化之發光層(如發光二極管或發光電化學電池)、一層對應 輕射能量且產生信號(有或無施加偏壓·)之材料(如光電偵 測管)。光電偵測管之實例包括光電導電池、光敏電阻、 光電開關、光電晶體、與光電管,及光電伏打電池,這些 名詞敘述於 Markus, John之Electronics and Nucle〇nk Dicti〇nary,47〇
與476(McGraw-Hill,1966) 〇 本發明之錯合物作為0LED之發射層之活性材料、或肩 14〇之電子運輸材料特別有用。較佳為,本發明之翻錯名 物作為二極管之發光材料。在用於層13〇時,已發現本潑 =之錯合物不需在固態基質稀釋劑中而有效。可使用基灰 1總重量為大於20重量%金屬錯合物,至多實質上 邀力 籾之層作為發射層。,,實質上100%”表示4 發=物為層中之唯一材料,與可能來自方法之雜質或倍
層1產物形成層。額外之材料可與金屬錯合物存在於發·
例如’可存在螢光染料以改變發 稀釋劑。& ^ +之顏色。亦可加A ^幸乂佳為,稀釋劑利於層中之電苻運_。^ 為聚人u Μ 电何運輸。稀釋劑月
。材料,如聚(Ν-乙稀基σ卡唑)與 分; ;丹歎矽烷0其亦可為/J ,如4,4’_Ν,Ν、二咔唑聯苯或第: 釋劑拄人μ 一方族胺。在使用制 ^時’金屬錯合物通常以少量存在,
量為小Μ Ο Λ 通吊基於層之總I 二夕於2 0重量%,較佳為少於1 0重量%。 - 〜種可用於本發明鉑金屬錯合物 聚合物,i由取X t稀釋劑型式為共奢 κ合物之三線激發狀態為比始錯合物之三勒 -18 - 200300790 (Η) —~……... 發明說明讀頁 激發狀態高之能量程度。適合之共, 、视聚合物之實例包括聚 伸方基亞乙烯、聚荞、聚噚二唑、 a本知、聚σ塞吩、聚0比 口定、聚伸笨基、其共聚物、及其組人 、 σ。共軛聚合物可為具 有,例如,丙烯酸、甲基丙烯酸、或 4乙烯基單體單位之非 共軏部份之共聚物。特別有用為第 ~< 均聚物與共聚物及經 取代第。 在某些情形,本發明之金屬錯合物 y 口物可存在超過一種異構
形式’或可存在不同錯合物之混合物。應了解在以上 OLEDs之討論中,名詞"金屬錯合物"意圖包含錯合物及 或異構物之混合物。
此裝置通常亦包括可相鄰陽極或陰極之撐體(未示最 常為,撐體相鄰陽極。撐體可為撓性或剛性、有機或無機 。通常使用玻璃或撓性有機膜作為撐體。陽極11〇可為注 射或收集正電荷載體特別有效之電極。陽極較佳為由含金 屬、混合金屬、合金 '金屬氧化物、或混合金屬氧化物之 材料製成。適合之金屬包括第Η族金屬、第4、5與6族金 屬、及第8 -1 0族過渡金屬。如果陽極為透光,則通常使用 第1 2、1 3與1 4族金屬之混合金屬氧化物,如銦錫氧化物。 陽極1 1 0亦可包含如聚苯胺之有機材料,如”Flexible ligh卜 emitting diodes made from soluble conducting polymers’丨,Nature 第 35 7卷,第 477-479 頁(1992年 6月 11 曰)。 陽極層1 1 0通常藉物理蒸氣沉積法或旋鑄法塗佈。名詞、 物理蒸氣沉積”指各種真空進行之沉積方式。因此,例如 ’物理蒸氣沉積包括所有之喷鍍形式(包括離子束噴鍍) -19- 200300790 (15) I發明説明績頁7 及所有之蒸氣沉積形式(如電子束蒸發與電阻蒸發)。可使 用之物理蒸氣沉積指定形式為rf磁控管喷鍍。 通常有相鄰陽極之電洞運輸層120。層120之電洞運輸材 料之實例已歸納於,例如,Y. Wang之Kirk-Othmer Encyclopedia of Chemical Technology,第 4版,第 18卷,第 837-860 頁,1996。 電洞運輸分子與聚合物均可使用。除了上述之TPD及 MPMP,常用之電洞運輸分子為:丨,丨·貳[(二-4·甲苯基胺 基)苯基]環己烷(TAPC) ; N,N’-貳(4_甲基苯基)-N,N,-貳 (4-乙基苯基)-[1,1’-(3,3,-二曱基)聯苯基]-4,4,-二胺 ^丁?0);肆-(3-甲基苯基)-1^,:^,;^’,:^’-2,5-伸苯二胺(?0八) ;α-苯基- 4-N,N-二苯基胺基笨乙烯(tps);對_(二乙胺基) 苯甲醛二苯基胼(DEH);三笨胺(TPA); 1-苯基-3-[對-(二 乙胺基)苯乙烯基]-5-[對-(二乙胺基)苯基]σ比唑啉(PPR或 DEASP) ; 1,2-反-雙(9Η-咔唑-9_ 基)環丁烧(DCZB); 1^,1^,1^’,1^’-肆(4-甲基苯基)-(1,1’-聯苯基)_4,4,-二胺(丁丁8) ’·及卟琳化合物,如酞氰銅。常用之電洞運輸聚合物為聚 乙烯基咔唾、(苯基甲基)聚矽烷、聚(3,4-乙二氧基噻吩 KPEDOT)、及聚苯胺。亦可藉由將如上所述之電洞運輸 分子摻雜至如聚笨乙烯與聚碳酸酯之聚合物中,而得到電 洞運輸聚合物。 選用層1 40可用以利於電子運輸,及作為防止層界面間 硬化反應之緩衝層或抗硬化層。較佳為,此層促進電子移 動力及減少硬化反應。選用層1 4 0用電子運輸材料之實例 包括金屬鉗合oxinoid化合物,如參(8·羥基喹寧基)銘(A1七) -20 - 200300790 (16) 發嗎說明續冥 ,啡啉為主化合物,如2,9 _二甲基-4,7 -二苯基-1,1 〇 _啡啉 (DDPA)或4,7-二苯基·uo-啡啉(DPA),及吡咯化合物, 如2-(仁聯笨基)_5气4_第三丁基苯基)-1,3,4-卩等二唑(Pbd) 與3-(4-聯笨基)_4_苯基-5-(4-第三丁基苯基)_1,2,4_三唑 (TAZ)。
陰極1 5 0為注射或收集電子或負電荷載體特別有效之電 極。陰極可為具有比第一電接觸層(在此情形,陽極)低之 作業函數之任何金屬或非金屬。用於第二電接觸層之材料 可選自第1族之鹼金屬(例如,Li、Cs)、第2族(鹼土)金屬 、第12族金屬、鑭系、及婀系。可使用如鋁、銦、舞、鎖 、釤、與鎂、及其組合。
已知有機電子裝置中具有其他層。例如,在導電性聚 物層1 2 0與活性層i 3 〇之間可有利於正電荷運輸及/或層 帶間隙相符,或作為保護層之層(未示)。類似地,活性 13 0與陰極層150之間可有利於負電荷運輸及/或層之帶 隙相符,或作為保護層之額外層(未示)。可使用^技I 知之層。此外,任何上述層可由二或更多層製成。或者 可將一些或全部無機陽極層110、導電性聚合物層12〇、 性層13〇、及陰極層150表面處理,以增加電荷載體運輸 率。用於各成分層之材料之選擇 ' 裝置效率之效率之目標而決定。 何択,、有 〇 應了解各功能層可由超過_層製成 裝置可藉由在適 可使用如玻璃及 當基材上循序 聚合膜之基材。 瘵氣沉積個別層而製備 可使用習知蒸氣沉積技 -21- (17)200300790 發明說明續頁 術’如熱蒸發、化學蒸氣沉積等。或者,可使用任何習知 塗覆技術由適當溶劑之溶液或分散液塗覆有機層。通常不 同之層具有以下之厚度範圍:陽極11〇, 5〇〇_5〇〇〇埃,較 佳為1 000-2000埃;電洞運輸層12〇, 5〇_25⑽埃較佳為 200-2000 埃;發光層 130, 1〇-1〇〇〇埃,較佳為 ι00·800 埃 ;選用電子運輸層⑷,50_ 1000埃,較佳為100_800埃;、
陰極1 50, 200-1 0,000埃,較佳為3〇〇_5〇〇〇埃。電子—電 洞重組區在裝置中之位置’因此及裝置之發射光譜,受各 層之相對厚度影響。例如’在使用如Α丨q 3之發射劑作為電 子運輸層時,電子一電洞重組區可在构3層。然後發射則 為Alq3而非所需之尖銳鑭系發射。因此必須選擇電子運輸 層之厚度使得電子一電洞重組區在發光層。層厚之所需比 例視所使用材料之確實本性而定。
應了解以金屬錯合物製造之本發明裝置之效率可藉由 將裝置中其他層最適化而進一步改良。例如,可使用如 Ca、Ba、Mg/Ag、或LiF/Al之更有效陽極。亦可應用造成 操作電壓降低或增加量子效率之成形基材及新穎電洞運 輸材料。亦可加入額外層以調整各層之能量程度及利於電 發光。 本發明之錯合物經常為磷光及光發光且可用於其他之 應用。例如’此錯合物可作為氧敏指示劑、在生物檢驗作 為磷光指示劑、及作為觸媒。 - 以下之實例描述本發明之特定特點及優點。其意圖為本 -22- 200300790
(18) 發明之描述而非限制。所有之百分比為莫耳百分比,除非 另有指示。 實例1 此實例描述母體配位基化合物2-(2,4-二氟苯基)-4-甲 氧基吡啶之製備。
在氮下將 2 -氯-4-甲氧基 〇比咬(Lancaster Synthesis,Inc.,3.50 克,24 ·4毫莫耳)、2,4-二氟苯基硼酸(Aldrich Chemical公司 ,3.85 克,24.4毫莫耳)、碳酸鉀(EM Science,6.74 克,48.8 莫耳)、肆三苯膦鈀(0)(Alddch Chemical公司,400毫克,0.346 毫莫耳)、二甲氧基乙烧(Aldrich,50毫升)、及水(50毫升 )在回流攪拌1 5小時。然後分離有機成分,及以3 X 2 5毫 升二乙醚萃取水性部份。組合有機部份以硫酸鈉乾燥且蒸 發至乾。生成之粗油以己烧/乙酸乙酯(6 : 1)作為溶離溶劑 藉矽膠急驟層析術純化,而提供所需產物如無色油,1 Η NMR為>9 5%純。隔離產率=3·8克(7 0%)。1HNMR(CDC13,296
Κ, 300 ΜΗζ):δ 8.52 (1H? d, J=5.9 Hz), 7.99 (1H, m), 7.27 (1H, dd5 J=2.1 及2.0 Hz),6.98 (1H,m),6.89 (1H,m),6·82 (1H,d,J=2.4 Hz),3.89 (3H, s) ppm. 19F NMR (CDC13, 296 K,282 MHz) δ=-109.05 (1F,dd,JF-F=li Hz 及JF-H=18 Hz),-112.80 (1F,brs) ppm. 實例2 此實例描述橋接氯二聚物[PtCl{2-(2,4-二氟苯基)·仁甲 氧基σ比啶}] 2之形成。 在氮下將得自實例1之2-(2,4 -二氟苯基)-4 -曱氧基α比咬 (1.50 克,6.79毫莫耳)、氣化鉑(H)(Strem Chemicals,1.641 -23- 200300790 (19) 發明:說明續頁 克,6.17毫莫耳)、氣化無水四丁銨(Aldrich Chemical公司 ,171毫克,0.617毫莫耳)、及氣苯(Aldrich)回流15小時 ,然後藉過濾隔離生成之沉澱產物,以甲醇清洗,及真空 乾燥,而提供所需產物如雜白色固體。隔離產率=2.31克 (7 5 %)。屮 NMR (DMSO-d6, 296 K,300 ΜΗζ):δ 9·32 (1H,d,J=7.0 Hz), 8.01 (1H,dd,J=10.8及2·4 Hz),7·50 (1H, dd, J=3.0及2·9 Hz),7.18 (1H, dd,J=6.9及2.7 Hz),7.05 (1H,m),3.99 (3H,s) ppm. 19F NMR (DMSO-d6, 296 K,282 MHz) δ=-106·79 (1F,dd,JF_F=11 Hz),-110.16 (IF, d,JF-F=11 Hz) ppm. 實例3 此實例描述化合物1-i,Pt(TMH){2-(2,4-二氟苯基)-4-曱氧基吡啶}之形成。 在120°C將得自實例2之[PtCl{2-(2,4-二氟苯基)-4 -曱氧 基吼啶}]2(2 00毫克,0.22毫莫耳)、2,2,6,6-四曱基- 3,5-庚二酮納鹽(由Aldrich Chemical公司之2,2,6,6 -四甲基-3,5 -庚二酮與Aldrich之氫化納製備;120毫克,0.56毫莫 耳)、及3 -乙氧基乙醇(Aldrich,20毫升)攪拌45分鐘。然 後真空移除揮發性成分,及將生成殘渣再溶於002(:12且以 CD2C12作為溶劑通過矽膠墊。收集藍色發光部份(Rf=l .0) 且蒸發至乾,而提供所需產物如乳白色固體。隔離產率 =2 12 毫克(80%)。iHNMRtCDfb,296 K,300 ΜΗζ): δ 8.76 (1H,d, J=6.8 Hz),7·51 (1H,dd,J=2.7及2.6 Hz),7.08 (1H,dd,J=8.7及2·3 Hz), 6·58 (1H,m),5·85 (1H,s),3·95 (3H,s),1·27 (18H,s) ppm. 19F NMR (CD2C12, 296 K,282 MHz) δ=-108·26 (1F,dd,JF-F=11 Hz),-113.36 (1F,d, 200300790 (20) JF.F=11 Hz) ppm. 以類似實例1-3之方式製備化合物Na至Nh,及丨-彳至i 實例4 此貫例描述使用本發明之鉑錯合物形成〇 L E D s。 藉熱蒸發技術製造包括電洞運輸層(HT層)、電發光層 (EL層)、及至少一個電子運輸層(ET層)之薄膜〇led裝置 。使用具油擴散泵之Edward Auto 306蒸發器。用於所有薄 膜沉積之基本真空為1〇·6托耳之範圍。沉積槽可沉積五種 不同之膜而無需中斷真空。 使用具有約1000-2000埃之ITO厚度之塗銦錫氧化物(itq) 玻璃基材。基材首先藉由以1N HC1溶液蝕刻不欲之IT〇區 域而圖樣化,以形成第一電極圖樣。使用聚醯亞胺帶作為 光罩。然後在水性清潔液中超音波清潔圖樣化j τ〇基材。 基材然後以蒸餾水繼而異丙醇清洗,然後在甲苯蒸氣中去 脂1-3小時。或者,使用得自Thin Film Devices, Inc.之圖樣 化ITO。這些1丁〇’5係以塗覆14〇(^IT〇塗層之c〇rningl737 玻璃為主,其具有3〇歐姆/平方之片電阻及8〇 %之透光度。 然後將已清潔、圖樣化IT 0基材裝入真空槽中且將槽下 泵至1〇4托耳。然後使用氧電漿將基材進一步清潔5-10分 鐘。在清潔後,然後藉熱蒸發將多層薄膜循序沉積在基材 上。最後經光罩沉積A1之圖樣化金屬電極。在沉積時使用 石英結晶監視器(Sycon STC-200)測量膜厚。實例中報告之 所有膜厚為假設沉積材料之密度為一而計算之公稱值。然 -25- 200300790 (21) fllgie 後自真空槽取出完成之OLED裝置且立即特徵化而不封包。 裝置層及厚度之結論示於表3。在所有之情形,陽極為 IΤ 〇,如以上所討論。 表3 樣品 HT層厚度,埃 EL層厚度,埃 ET層厚度,埃 陰極厚度,埃 1 MPMP 化合物1 -a DPA A1 511 412 408 737 2 MPMP 化合物1-b DPA A1 507 421 407 725 3 MPMP 化合物1-c DPA A1 507 419 415 738 4 MPMP 化合物1-d DPA A1 534 420 405 729 5 MPMP 化合物1-e DPA A1 616 404 406 730 6 MPMP 化合物1-f DPA A1 521 430 401 728 7 MPMP 化合物1-g DPA A1 518 407 418 727 8 MPMMP 化合物1 -h DPA A1 532 570 412 600 9 MPMP 化合物1-i DPA A1 528 418 404 736 10 MPMP 化合物1 -j DPA A1 514 483 416 727 11 MPMP 化合物1-k DPA A1 519 423 403 721 12 MPMP 化合物Μ DPA A1 525 411 412 752 13 MPMP 化合物1-m DPA A1 _ 550 406 409 918
〇?八=4,7-二苯基-1,10-啡啉 ET=電子運輸 EL=電發光 -26- 200300790 發曰月說明續頁 (22) Η T =電洞運輸 ΜΡΜΡ =戴[4-(Ν,Ν-二乙胺基)-2-甲基本基](4-甲基苯基) 甲烷 OLED樣品係藉由測量其(1)電流一電壓(I-V)曲線,(2) 電發光輻射相對電壓,及(3)電發光光譜相對電壓而特徵 化。使用之裝置200示於圖10。OLED樣品220之Kv曲線係 以 Keithley Source-Measurement Unit 237 型 280 測量。以 Minolta LS-110發光計測量電發光輻射(單位為Cd/平方公 尺)vs·電壓,而使用Keithley SMU掃描電壓。電發光光譜 係藉由使用一對鏡片23〇將光經電子光柵24〇散佈於光譜 儀250而收集光,然後以二極管陣列偵測器26〇測量而得到 。同時實行所有三種測量且以電腦270控㈣。在特定電壓 之裝置效率係藉由將LED之電發光輻射除以裝置運行所 需之電流密度而決定。單位為Cd/A。 結果示於以 下表4。 鉑化合物之電發本从肪 樣品 峰輻射 Λ / rri ^ ------- 1 一 峰效率 Cd/A 峰大約波長 nm 1 Cl/ 111 8 〜_於19 V 0.15 620 2 0.02 於 15 V 3 30 、^於 19 V -------- 0.6 600及640 4 80 於20 V 0.38 640及690 5 w、么 V/ Y 25 s於20 V 0.3 --—-— 600及640 -27- 200300790 (23) 發明說明續頁 6 120 於19 V 1.7 590及640 7 16 於20 V 0.4 540 8 60 於21 V ——--- 4 ’ 475及505 9 130 於23 V 4 ’ 458及489 10 80 於20 V 7 ' 476及508 11 '1----- 0.2 於23 V 0.035 12 90 於19 V 4.5 473及507 13 7〇〇 於22 V 9 474及507 t例5(預示性) 此實例描述在聚(第)聚合物基質中使用本發明之紅色 發光P t材料形成〇 L E D ’ s。使用生成摻合物作為〇 L E D之活 性紅色發射層。如實例3所述製備鉑錯合物pt(acac){ 1-(5_ 第二丁基本基)異堕寧},表1之化合物1-c。如Yamamoto 之 Progress in Polymer Science,第 17卷,第 1153 頁(1992) 所述而製備聚苐,其中將單聚單位之二_ (較佳為二溴) 衍生物與化學計量之零價鎳化合物(如貳(丨,5 -環辛二烯) 鎳(〇))反應。 此實例中之有機膜成分均為溶液處理。裝置組件如下··-如貫例4所述將ιτο /玻璃基材(Applied Films)圖樣化(裝置 有效面積==全部3平方公分)及清潔。基材藉由置於3〇〇瓦電 聚烤箱中1 5分鐘而進一步清潔。將聚(乙二氧基噻吩)一聚 -28- (24) 200300790
(苯乙烯磺酸)(PEDOT-PSSA,BaverA n、/ yer公司)緩衝層(即,電洞 運輸/注射層)旋塗至9 0奈米之厚唐。时+ 。 子度。膜在200°C加熱板上 乾燥3分鐘。然後將基材轉移至充填f L , u臀I手套箱,此時將聚( 第)聚合物溶液、[Pt(acac){i_(5_第三丁基苯基)異膣寧 }](1·6微莫耳)、與無水甲苯(7·5亳升)旋塗至基材上至7〇 奈米之厚度。然後將基材轉移至高真空槽,在以2·〇 χ 1〇_0 托耳熱沉積Ba(3.5奈米)繼而Al(400奈米)。使用υν-可硬
化壞氧樹脂將玻璃片膠合在陰極頂部而使生成〇 L ε D裝置 為氣密。 此裝置藉由獲得電流一電壓、發光一電壓、發光一電流 、效率一電壓、及效率一電流外形而完全特徵化。其係使 用電腦驅動(Labview軟體)Keithley Source-Measurement Unit 及光電二極管完成,後者整合在全部3平方公分裝置有效 面積之光輸出。 圖式代表符號說明
100 裝置 11〇 陽極層 120 電洞注射/運輸層 130 光活性層 140 選用層 15 0 陰極層 200 裝置 220 0LED 樣品 23 0 鏡片 -29- 200300790
(25) 240 電子光柵 2 50 光譜儀 260 二極管陣列偵測器 270 電腦 2 8 0 Keithley Source-Measurement Unit 237型
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Claims (1)
- 200300790 、申請專利範圍 一種活性層,其包含至少 一種具有選自式I與式II之化 合物: PtLlL2 (I) ?tVVL4 (II) 其中: 在式i中: L2為單陰離子性雙牙配位基; 在式II中: L3為單牙配位基;及 L4為單牙膦配位基; 在式I與II中: L1選自圖1所示之式III,及圖2所示之式VII,其中: 在式III與VII中: E1至E4在各情形為相同或不同,而且為CR2或N ; R2在各情形為相同或不同,而且選自H、D、Cn(H + F)2n + ; 、F、OCn(H + F)2n + i、OCF2Y、SR3、與 N(R3)2,或 相鄰R2基可結合形成5 -或6-貝環; R3為 Η、CnH2n + 1 ; Y為 Η、Cl、或 Br; η為1至12之整數; - 在式III中: Α為Ν或SR3 ; R1在各情形為相同或不同,而且選自D、Cn(H+F)2n+ 200300790 申請:專利範圍績 、F、OCn(H+F)2n+i、OCF2Y、SR3、與N(R3)2,或相鄰 R基可 結合形成5 -或6 -員環; α為0、1或2 ;及 在式VII中: R4至R7在各情形為相同或不同,而且選自H、D、 Cn(H+F)2n+1、F、OCJH+FLnw、OCF2Y、SR3、與N(R3)2,或 相鄰R基可結合形成5-或6 -員環; 其條件為,在活性層含少於2 0重量%之此至少一種化合 物之處,亦存在稀釋劑。 2.根據申請專利範圍第1項之活性層,其中E1至E4為CR2 及至少一個 R2 選自 D、Cn(F)2n+1、F、OCn(F)2n+1、與OCF2Y。 3 .根據申請專利範圍第1或2項之活性層,其中L 1具有選自 圖1所示之式IV、式V與式VI之式,其中δ為0或1至4之 整數,或L1具有選自圖2所示之式VIII、式IX與式X之式 ,其中δ為0或1至4之整數,或L1具有式III,Ε1至Ε4至少 之一為CR2,及R2選自D、F、CF3、與OCF3,或L1選自 式IV、式V與式VI,α為0,及至少一個R1選自D、F、 CF3、與OCF3,或L1具有式VII,Ε1至Ε4至少之一為CR2 ,及R2選自D、F、CF3、與OCF3,或L1選自式VIII、式 IX與式X,及至少一個R1選自D、F、CF3、與OCF3。 4.根據申請專利範圍第1或2項之活性層,其中L3為單陰離 子性且L4為非離子性。 5 .根據申請專利範圍第1或2項之活性層,其中化合物具有 式I且L2選自烯醇基、胺基羧酸基、亞胺基羧酸基、 柳酸基、羥基膣寧基、及二芳基膦基烷氧化物。 -2- 200300790 申請專利範圍績頁 6 .根據申請專利範圍第1或2項之活性層,其中化合物具有 式11且L3包含選自以下之配位基:烷氧化物、羧酸基、 硫羧酸基、二硫羧酸基、磺酸基、硫醇基、胺甲酸基、 二硫胺甲酸基、硫卡腙陰離子、磺醯胺陰離子、li化物 、石肖酸基、硫酸基、與六鹵銻酸基。 7 .根據申請專利範圍第1或2項之活性層,其中至少一種化 合物具有式II且L4具有式ΧΠΙ, PAr3 (XIII) 其中Ar選自芳基與雜芳基。 8 ·根據申請專利範圍第1或2項之活性層,其中實質上1 00 重量%之活性層包含至少一種具有選自式I與式II之化 合物。 9. 根據申請專利範圍第1或2項之活性層,其中稀釋劑選自 聚(N-乙烯基咔唑);聚矽烷;4,4’-N,N’-二咔唑聯苯; 與第三芳族胺;或稀釋劑為共軛聚合物,其選自聚伸芳 基亞乙烯、聚苐、聚噚二唑、聚苯胺、聚噻吩、聚吡啶 、聚伸笨基、其共聚物、及其組合。 10. 根據申請專利範圍第1或2項之活性層,其中至少一種 化合物選自表1所示之錯合物Ι-a至1-m。 11. 一種化合物,其選自表1所示之錯合物1-a至1-m。 12. —種有機電子裝置,其包含一個根據申請專利範圍第1 項之活性層。 13. 根據申請專利範圍第12項之裝置,其中E1至E4為CR2及 至少一個 R2選自 D、Cn(F)2n+1、F、OCn(F)2n+1、與OCF2Y。 200300790 申着專利範®讀頁 14. 根據申請專利範圍第12項之裝置,其中L1具有選自圖1 所示之式IV、式V與式VI之式,其中δ為0或1至4之整數 ,或L1具有選自圖2所示之式VIII、式IX與式X之式,其 中δ為0或1至4之整數,或L1具有式III,Ε1至Ε4至少之一 為CR2,及R2選自D、F、CF3、與OCF3,或L1選自式IV 、式V與式VI,α為0,及至少一個R1選自D、F、CF3、 與OCF3,或L1具有式VII,E1至E4至少之一為CR2,及R2 選自D、F、CF3、與OCF3,或L1選自式VIII、式IX與式 X,及至少一個R1選自D、F、CF3、與OCF3。 15. 根據申請專利範圍第12或14項之裝置,其中L3為單陰離 子性且L4為非離子性。 16. 根據申請專利範圍第12或14項之裝置,其中化合物具 有式I且L2選自β-烯醇基、胺基羧酸基、亞胺基羧酸基 、柳酸基、羥基喹寧基、及二芳基膦基烷氧化物。 17. 根據申請專利範圍第12或14項之裝置,其中化合物具 有式II且L3包含選自以下之配位基:烷氧化物、羧酸基 、硫羧酸基、二硫羧酸基、磺酸基、硫醇基、胺甲酸基 、二硫胺甲酸基、硫卡腙陰離子、磺醯胺陰離子、li化 物、硝酸基、硫酸基、與六鹵錄酸基。 18. 根據申請專利範圍第12或14項之裝置,其中至少一種 化合物具有式II且L4具有式XIII, PAr3 (XIII) 一 其中Αι·選自芳基與雜芳基。 19.根據申請專利範圍第12或14項之裝置,其中實質上100 200300790 申請專利範園續頁 重量%之活性層包含至少一種具有選自式I與式11之化 合物。 20. 根據申請專利範圍第1 2或1 4項之裝置,其中活性層為 電荷運輸層。 21. 根據申請專利範圍第12或14項之裝置,其中稀釋劑選 自聚(N -乙烯基咔唑);聚矽烷;4,4’-N,N’-二咔唑聯苯 :與第三芳族胺;或稀釋劑為共軛聚合物,其選自聚伸 芳基亞乙烯、聚苐、聚噚二唑、聚苯胺、聚噻吩、聚。比 啶、聚伸苯基、其共聚物、及其組合。 22. 根據申請專利範圍第1 2或1 4項之裝置,其更包含: 一電洞運輸層,其選自N,N’-二苯基-N,N’-雙(3 -甲基 苯基)-[1,1’-聯苯基]-4,4’-二胺;1,1-雙[(二-4 -曱苯基 胺基)苯基]環己烷;N,N’-雙(4 -曱基苯基)-N,N’-雙(4-乙基苯基)-[1,1’-(3,3’-二甲基)聯苯基]-4,4’-二胺;肆-(3 -甲基苯基)-Ν,Ν,Ν’,Ν’-2,5 -伸苯二胺;α-苯基-4-Ν,Ν-二苯基胺基苯乙烯;對-(二乙胺基)苯甲醛二苯基 :三苯胺;雙[4-(Ν,Ν-二乙胺基)-2 -甲基苯基](4 -甲基 苯基)甲烷;1-苯基-3-[對-(二乙胺基)苯乙烯基]-5-[對-(二乙胺基)笨基]吨唑啉;1,2-反-雙(9Η-咔唑-9-基)環 丁烷;Ν,Ν,Ν’,Ν’-肆(4 -甲基苯基)-(1,1’-聯苯基)-4,4’-二胺;卟啉化合物;及其組合;及/或 一電子運輸層,其選自叁(8-羥基膣寧基)鋁;2,9-二 甲基-4,7 -二苯基-1,10-啡啉;4,7 -二苯基-1,10-啡啉; 2 - (4 -聯苯基)-5-(4-第二丁 基苯基)-1,3,4 - Β等二 σ圭,3 - (4 - 200300790聯苯基)-4 -苯基- 5- (4_第二丁基苯基)-1,2,4-三σ坐;萎 (2 -苯基σ比唆)鉉;及其組合。 23.根據申請專利範圍第12或14項之裝置,其中至少一種 化合物選自表1所示之錯合物Ι-a至1-m。
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- 2002-11-04 CA CA002466119A patent/CA2466119A1/en not_active Abandoned
- 2002-11-04 JP JP2003542297A patent/JP2005508438A/ja active Pending
- 2002-11-04 EP EP02789431A patent/EP1442095A1/en not_active Withdrawn
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JP2005508438A (ja) | 2005-03-31 |
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US7517594B2 (en) | 2009-04-14 |
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CA2466119A1 (en) | 2003-05-15 |
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