TW200946635A - Organic electroluminescent devices - Google Patents
Organic electroluminescent devices Download PDFInfo
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Description
200946635 九、發明說明 【發明所屬之技術領域】 本發明關於發磷光之有機電致發光裝置,其含有式(I) ‘之金屬錯合物作爲發射層的基質材料。 【先前技術】 使用有機半導體作爲功能性材料的有機電致發光裝置 〇 (OLED)之結構被敘述在例如 US 4539507、US 51 5 1629、EP 0676461 及 WO 98/27136 中。近年來,漸漸 增加使用展現代替發螢光的發磷光之有機金屬錯合物(M. A. Baldo 等人之 Appl. Phys· Lett. 1 999,75, 4-6 )。以量 子-機械的理由而言,使用有機金屬化合物作爲發磷光之 發射體有可能增加高至4倍的能量及功率效能。通常,在 呈現三重態發射的0LED中仍有相當多的問題。例如,發 磷光之0LED的物理性質仍有關於在高品質及長壽命的電 © 致發光裝置中使用三重態發射體的效能、操作電壓及壽命 的不滿意度。 根據先前技藝’ 4,4’-雙(N-味哩基)聯苯(CBP)常被 用作發磷光之OLED中的基質材料。缺點是以其所製造之 裝置具有短壽命及高操作電壓,其造成低的功率效能。另 外’ CBP具有不當的高玻璃轉換溫度。雖然CPB有缺 點’但是其持續被用作三重態材料,因爲上述的問題也還 無法使用可替換的基質材料而加以滿意地解決。 此外’已知鋁錯合物(特別爲B-Alq )作爲三重態基 200946635 質材料(例如 ’ Chem. Phys. Lett. 2005, 404,121-125 )。 US 2006/0401 39敘述使用具有以希夫(Schiff)鹼爲 主之配位基的金屬錯合物作爲光活性材料的主體材料。然 . 而,僅揭示具有三價金屬的錯合物,特別爲五-或六配位 之鋁錯合物。 【發明內容】 © 本發明的目的係提供三重態基質材料,與先前技藝相 比,其具有足夠高的玻璃轉換溫度及非常好的熱穩定性和 具有水解穩定性,且改善有機電致發光裝置中的效能、壽 命及操作壓力。 驚訝地發現其中配位基係經由兩個亞胺氮原子與金屬 配位的某些具有二價金屬離子的金屬螯合物展現明顯的改 進,特別關於壽命、效能、對溫度應力的穩定性、玻璃轉 換溫度及水解穩定性。亦可具有二聚物形式的該等錯合物 〇 含有以正方平面、四面體或假四面體配位的呈氧化態+Π 的四配位金屬離子。本發明因此關於發磷光之電致發光裝 置,其含有該等錯合物作爲在發射層中的基質材料。 本發明因此關於有機電致發光裝置,其包含在發射層 中的至少一種發磷光化合物及至少一種式(I)化合物: -6 - 200946635
式0) 其中下述適用於所使用的符號及下標: Μ 在各次出現係相同或不同地爲具有氧化態+Π的 金屬離子,其係選自 Be、Mg、Ca、Sr、Ba、 F e、R u、O s、C ο、N i、P d、C u、Z n、C d、H g、 Sn 及 Pb ; x 在各次出現係相同或不同地爲0、s或co-o;
Ar1爲具有5至60個芳香族環原子之芳香族或雜芳 香族環系統,其可被一或多個R基取代且其中 各個芳香族基團可經由具有1至10個C原子之 伸烷基互相連結,另外,其中一或多個未鄰接之 C原子可被Ο或S替換;
Ar2在各次出現係相同或不同地爲具有5至60個芳 香族環原子之芳香族或雜芳香族環系統,其可被 一或多個R基取代; Y 在各次出現係相同或不同地爲單鍵或具有1至 10個C原子之伸烷基,另外,其中未與氮鍵結 的一或多個未鄰接之C原子可被〇替換且可被 200946635 一或多個R基取代; R 在各次出現係相同或不同地爲H、F、Cl、Br、 I、N(R2)2、CN、N〇2 · Si(R2)3、B(OR2)2、 C( = 0)R2、P( = 〇)(R2)2、S( = 0)R2、S( = 〇)2R2、 . OSO2R2、具有1至40個C原子之直鏈烷基、烷 氧基或硫烷基或具有3至40個C原子之分枝或 環狀烷基、烷氧基或硫烷基,每個該等基團可被 一或多個R2基取代’其中一或多個未鄰接之 0 CH2 基團可被 R2C = CR2、C 三 C、Si(R2)2、
Ge(R2)2、Sn(R2)2、C = 0、C = S、C = Se、C=NR2、 P( = 0)(R2)、SO、S02、NR2、O、S 或 CONR2 替 換,且其中一或多個H原子可被F、Cl、Br、 I、CN或NO2替換,或爲具有5至60個芳香族 環原子之芳香族或雜芳香族環系統,每個該等基 團可被一或多個R2基取代,或爲具有5至60個 芳香族環原子之芳氧基或雜芳氧基,其可被一或 〇 多個R2基取代,或爲該等系統之組合;二或多 個取代基R在此亦可互相形成單一或多環脂肪 — 族或芳香族環系統; R1 在各次出現係相同或不同地爲H、F、CF3、具有 1至40個C原子之直鏈院基或具有3至40個C 原子之分枝或環狀院基’每個該等基團可被一或 多個R2基取代’其中一或多個未鄰接之CH2基 團可被 R2C = CR2、C ξ C、Si(R2)2 ' Ge(R2)2、 -8 - 200946635
Sn(R2)2替換,且其中一或多個Η原子可被F、 Cl、Br'I、CN或N02替換,或爲具有5至60 _ 個芳香族環原子之芳香族或雜芳香族環系統,每 -個該等基團可被一或多個R2基取代,或爲該等 系統之組合;R1在此亦可與一或多個取代基R 形成單一或多環脂肪族或芳香族環系統; R2 在各次出現係相同或不同地爲H、F或具有1至 〇 20個C原子之脂肪族、芳香族或雜芳香族烴 基,另外,其中一或多個Η原子可被F替換; 二或多個取代基R2在此亦可互相形成單-或多 環脂肪族或芳香族環系統; η 在各次出現係相同或不同地爲0、1或2。 式(I)化合物較佳地具有大於100°c之玻璃轉換溫度 Tg,特佳地大於120°C。 就本發明的目的而言,發磷光化合物意指其從具有較 © 高的自旋多重性,亦即自旋態> 1之激發態(特別從激發 之三重態)發光的化合物。在此發射可從純三重態或從以 ' 三重態參與的混合態發生。就本發明的目的而言,任何從 銥或鉛錯合物的發光意指發磷光。 就本發明的目的而言,芳基含有6至40個C原子; 就本發明的目的而言,雜芳基含有2至40個C原子及至 少一個雜原子,其先決條件係C原子與雜原子之總數是至 少5個。雜原子較佳地選自N、〇及S。芳基或雜芳基在 此意指簡單芳香族環(亦即苯)或簡單雜芳香族環(例 -9 - 200946635 如,吡啶、嘧啶、噻吩)或縮合之芳基或雜芳基(例如, 萘、蒽、菲、喹啉、異喹啉)。 就本發明的目的而言,芳香族環系統含有6至40個 ' 的C原子在環系統中。就本發明的目的而言,雜芳香族環 系統含有2至40個C原子及至少一個雜原子在環系統 中,其先決條件係C原子與雜原子之總數是至少5個。雜 原子較佳地選自N、0及S。就本發明的目的而言,芳香 族或雜芳香族環系統意指不一定只含有芳基或雜芳基,反 © 而其中數個芳基或雜芳基亦可被非芳香族單元(較佳地小 於10%之原子不是H)中斷之系統,例如sp3混成之C、 N或Ο原子。因此,例如,諸如9,9’-螺旋二芴、9,9-二芳 芴、三芳胺、二芳醚、二苯乙烯之系統亦就本發明的目的 而被認爲是芳香族環系統,且同樣被認爲是其中二或多個 芳基例如被直鏈或環狀烷基或甲矽烷基中斷之系統。 就本發明的目的而言,C!-至C4G-烷基(另外,其中個 別的Η原子或CH2基團可被上述基團取代)較佳地意指甲 Ο 基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁 基、第三丁基、2-甲基丁基、正戊基、第二戊基、環戊 — 基、正己基、環己基、正庚基、環庚基、正辛基、環辛 基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙 基、乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯 基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、 乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛 炔基。-至 C4Q-烷氧基較佳地意指甲氧基、三氟甲氧 -10- 200946635 基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧 基、第二丁氧基、第三丁氧基或2-甲基丁氧基。具有5 至40個芳香族環原子之芳香族或雜芳香族系統(其亦可 - 在每個例子中被上述R基取代且可由任何所欲位置與芳 香族或雜芳香族環系統連結)特別意指從苯、萘、蒽、 菲、芘、筷、苯並蒽、茈、螢蒽、苯並螢蒽、並四苯、稠 五苯、苯並芘、二苯並蒽、聯苯、聯苯撐、三聯苯、三聯 〇 苯撐、芴、螺旋二芴、二氫菲、二氫芘、四氫芘、順一或 反-節並苟、順—或反-單苯並節並苟、順一或反—二苯 並茚並芴、三聚茚、異三聚茚、螺旋三聚茚、螺旋異三聚 茚、呋喃、苯並呋喃、異苯並呋喃、二苯並呋喃、噻吩、 苯並噻吩、異苯並噻吩、二苯並噻吩、吡咯、吲哚、異吲 哚、咔唑、吡啶、喹啉、異唾啉、吖啶、菲啶、苯並_5,6-喹啉、苯並-6,7 -喹啉、苯並-7,8 -喹啉、吩噻哄、吩噁 哄、妣哩、苗嗖、咪哩、苯並咪唑、萘咪哩、菲咪哩、耻 〇 啶咪唑、吡哄咪唑、喹噁啉咪唑、噁唑、苯並噁唑、萘噁 哩、惠嚼哇、菲嚼哩、異喔哩、丨,2 -噻哩、1,3_噻哩、苯 ' 並噻唑、嗒哄、苯並嗒哄、嘧啶、苯並嘧啶、喹噁啉、 1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、丨,6-二氮雜 拓、1,8-二氮雜芘、4,5-二氮雜芘、4,5,9,10-四氮雜茈、 吡畊、吩哄、菲噁哄、菲噻哄、螢紅環、萘啶、氮雜咔 嗤、苯並味琳、菲繞啉、1,2,3 -三嗤、丨,2,4·二哩、本並二 唑、1,2,3-噁二唑、1,2,4 -噁二唑、I,2,5·噁二唑、丨,3,4-噁二唑、1,2,3 -噻二唑、1,2,4-噻二唑、丨,2,5·噻二唑、 -11 - 200946635 1,3,4-噻二唑、1,3,5-三哄、1,2,4-三畊、1,2,3-三畊、四 唑、1,2,4,5-四畊、1,2,3,4-四畊、1,2,3,5-四阱、嘌呤、蝶 啶、吲哚畊及苯並噻二唑所衍生之基團。 ^ 在本發明較佳的具體實例中,金屬Μ係選自Be、 ·
Mg、Pd、Zn或Cd。金屬Μ特佳爲Zn。 指數n更佳爲0或1。指數η特佳爲0。 符號Υ更佳地在各次出現係相同或不同地代表單鍵 或C(R)2基團,特佳地代表單鍵。 0 符號X更佳地在各次出現係相同或不同地代表Ο或 S,特佳地代表0。 特別優先選擇其中上述的優先選擇同時存在的式(I) 化合物,亦即其中金屬 Μ係選自 Be、Mg、Pd、Zn或 Cd,且其中指數n = 〇或1,且其中符號Y在各次出現係相 同或不同地代表單鍵或C(R)2基團,且其中符號X在各次 出現係相同或不同地代表Ο或S之化合物。最特別優先 選擇其中金屬Μ爲Zn,且其中指數n = 0,且其中符號Y 〇 代表單鍵,且其中符號X代表Ο之式(I)化合物。 就n = 0之符號Ar1更佳地代表具有5至24個芳香族 _ 環原子之芳香族或雜芳香族環系統,每個該等基團可被一 或多個R基取代。就n = 0之基團Υ-Αι^-Υ特佳地代表下 式(II)至(XV)之基團: -12- 200946635
就n=l之符號Ar1更佳地代表具有5至24個芳香族 環原子之芳香族或雜芳香族環系統,特別是具有6至12 © 個芳香族環原子’每個該等基團可被一或多個R基取代。 就n=l之基團Ar1特佳地代表下式(XVI)至(XXI)之基團: -13- 200946635
在式(π)至(XXI)中的虛線鍵在每個例子中代表與亞胺 氮之連結。在式(XIX)中的指數m爲1至10。 特別優先選擇同時具有上述就Μ、η、Y和X的優先 選擇及選自上述式(II)至(XXI)之基團Ar1的式(I)化合物。 符號Ar2更佳地在各次出現係相同或不同地代表具有 5至16個芳香族環原子之芳基或雜芳基,其可被一或多 個R基取代。符號Ar2特佳地在各次出現係相同或不同地 代表選自苯基、1-或2-萘基、4-聯苯基、1-或2-蒽基,2-或3 -噻吩基、2 -或3 -吡咯基、2 -或3 -呋喃基、2-、3 -或4-吡啶基、3-或4-嗒哄基、4-或5·嘧啶基、吡哄基、2-、3-、4-、5-、6-、7-或 8_ 喹啉基或 3-、4-、5-、6-、7-或 8-異喹啉基之芳基或雜芳基,每個該等基團可被一或多個R 基取代。最特別優先選擇苯基、1-萘基、2-萘基及4-聯苯 基’特別爲苯基,每個該等基團可被一或多個!^基取代。 特別優先選擇同時具有上述較佳的基團Ar2及選自上 述式(Π)至(XXI)之基團Ar1的式⑴化合物。最特別優先選 -14- 200946635 擇同時具有上述就Μ、η、Υ、Χ和Ar2及選自上述式(II) 至(XV)之基團Ar1的式(I)化合物。 : 符號R更佳地在各次出現係相同或不同地代表Η、 F、N(R2h、Si(R2)3、C( = 0)R2、P( = 〇)(R2)2、具有 1 至 10 個C原子之直鏈烷基或具有3至10個C原子之分枝或環 狀烷基,每個該等基團可被一或多個R2基取代,其中一 或多個未鄰接之CH2基團可被R2C = CR2、Ο或S替換,且 〇 —或多個Η原子可被F替換,或代表具有5至16個芳香 族環原子之芳基或雜芳基,每個該等基團可被一或多個 R2基取代,或代表該等系統之組合;二或多個取代基R 在此亦可互相形成單-或多環脂肪族或芳香族環系統。符 號R特佳地在各次出現係相同或不同地代表Η、F、具有 1至4個C原子之直鏈烷基或具有3或4個C原子之分枝 烷基’每個該等基圑可被一或多個R2基取代,其中一或 多個Η原子可被F替換,或代表具有6至10個芳香族環 ® 原子之芳基’該等基團在每個例子中可被一或多個R2基 取代;二或多個取代基R在此亦可互相形成單—或多環脂 肪族或芳香族環系統。 符1號R1更佳地在各次出現係相同或不同地代表Η、 具有1至6個C原子之直鏈烷基或具有3至6個C原子 之分枝或環狀烷基,其中在每個例子中的一或多個Η原 子亦可被F替換,或代表具有5至16個芳香族環原子之 芳基或雜芳基,每個該等基團可被一或多個R2基取代。 符號R1特佳地在各次出現係相同或不同地代表Η、甲基 -15- 200946635 或苯基或萘基’每個該等基團可被一或多個R2基取代。 式(I)化合物可選擇地爲呈固態的二聚物或寡聚物形 式’且-不一定爲簡單的錯合物形式,如以式(〗)中的簡化 形式所描述。含有二聚物或寡聚物形式之式⑴化合物的 有機電致發光裝置因此自然由本發明以與含有式(I)化合 物作爲簡單錯合物的電致發光裝置相同的方式所涵蓋。 更優先選擇對稱化合物,亦即其中所有符號Ar2是相 同的,所有符號X是相同的,所有符號R1是相同的,所 © 有符號Y是相同的,且被同樣地取代之化合物。 含有式(I)之結構成分的較佳化合物的實例爲下述之 化合物(1)至(180):
-16- 200946635
-17- 200946635
(21)
(22)
-18- 200946635
G31) (32) 19- 200946635
(33) (34)
ch3 ch3 (37)
CH,
Η3°Ύ^Ν~~^Ζη-一n^CH3☆ '方(40) h3c^n〜:z,v--N^CH3
(41) (42) 20- 200946635
-21 - 200946635
(61) (62)
22- 200946635
-23- 200946635
-24- 200946635
(83) (84)
(90)
-25- 200946635 (92) (91)
(99)
26- 200946635
(105) (106)
(107)
(108)
-27- 200946635
(115) (116)
-28- 200946635
(119)
(125)
(127) (120)
(128)
-29 200946635
(131)
(134)
'一 ΎSXX)
(136) (135)
(137)
(138)
30- (139) 200946635
(141)
(142)
(146)
(148)
-31 - 200946635 (150) (149)
(155)
(156) Ο
-32- 200946635
(161)
(158)
(162) -33- 200946635
--Pd--卜 ,〇/ \〇、 (167)
9-9
-34- 200946635 ❹
(177) ❹
(179) (178)
(180) 式(I)化合物可以標準的有機化學方法合成。特別 地,有兩種合成可能性適合於本文。因此,首先有可能從 對應之二胺及醛或酮隨著希夫鹼的形成而合成配位基,接 著在進一步的步驟中與適合的金屬鹽反應,得到對應之金 屬錯合物。亦更有可能在一個步驟中進行配位基合成及錯 合反應(模板合成),其係藉由二胺、醛或酮及適合的金 屬鹽同時互相反應(Eur. J. Inorg. Chem. 2004, 456卜 -35- 200946635 65 ) ° 式(I)化合物適合作爲在有機電致發光裝置中的發射 層中所使用的發磷光之發射體的基質材料。 -' 本發明因此更關於式(I)化合物作爲在有機電致發光 裝置中的發磷光化合物之基質材料的用途。 有機電致發光裝置包含陰極、陽極及至少一層發射 層。除了該等層以外,其亦可包含更多層,例如在每個例 子中的一或多個電洞注射層、電洞傳輸層、電子阻斷層、 © 電洞阻斷層、電子傳輸層、電子注射層、電荷產生層 (IDMC 2003 , Taiwan ; Session 21 OLED (5), T.
Matsumoto, Τ. Nakada, J. Endo, K. Mori, N. Kawamura, A.
Yokoi, J. Kido 之 Multiphoton Organic EL Device Having Charge Generation Layer)及/或有機或無機p/n接面。同 樣有可能將具有例如激發阻斷功能的中間層引入兩個發射 層之間。然而,應指出每個該等層不一定必須存在。 在本發明較佳的具體實施例中,包含式(I)化合物及 © 發磷光之發射體的發射層爲紅光-、綠光-或藍光-發射 層。 在本發明更佳的具體實施例中,有機電致發光裝置包 含數層發射層,其中至少一層包含至少—種式(I)化合物 及至少一種發磷光化合物。發射層特佳地總共具有最大介 於3 80奈米至750奈米之間的數種發射,整體上造成白光 發射,亦即將能夠發螢光或發磷光的各種發射化合物用在 發射層中。特別優先選擇三層系統,其中該三層展現藍、 -36- 200946635 綠及橘或紅色發射(基礎結構參見例如WO 05/01 1013 )0 發磷光化合物(=三重態發射體)包含至少一種在適 -合的激發時發射較佳地在可見光區中的光線且另外含有至 少一種具有原子數大於20,較佳地大於38及小於84,特 佳地大於56及小於80的原子之化合物。所使用的發磷光 之發射體較佳爲含有銅、鉬、鎢、銶、釕、餓、鍺、銥、 〇 鈀、鉑、銀、金或銪之化合物,特別爲含有銥或鉑之化合 物。 特佳的有機電致發光裝置含有至少一種式(XXII)至 (XXV)化合物作爲發磷光之發射體: A——lr〔 )Cy_ < tri L CCy」 2 _ CCy (XXIII) -DCy DCy (XXII)
A—Pt: 、CCy p< CCy (XXV) (XXIV) 其中R具有與上述式(i)之相同意義,且下述適用於 所使用的其他符號: DCy &名·次出現係相同或不同地爲環狀基團,其含有 個施體原子,較佳爲氮、碳烯形式的碳或 @ ’壤狀基團經由其與金屬鍵結,且其可依次攜 -37- 200946635 帶一或多個取代基R;基團DCy及CCy可經由 共價鍵互相連接; CCy在各次出現係相同或不同地爲環狀基團,其含有 碳原子,環狀基團經由其與金屬鍵結,且其可依 次攜帶一或多個取代基R; A 在各次出現係相同或不同地爲單陰離子、雙牙螯 合配位基,較佳爲二酮根(diketonate )配位 基。 在數個R基之間形成的環系統亦可產生在基團DCy 與CCy之間的橋。
上述之發射體的實例被揭露於申請案WO 00/70655、 W0 01/41512 、 W0 02/02714 、 WO 02/1 5645 、 EP 1191613、EP 1191612、EP 1191614 及 W0 05/033244 中。通常,適合的發磷光錯合物爲所有那些如根據先前技 藝用於發磷光之〇LED且如熟習有機電致發光之領域的本 技藝者已知的錯合物。 至少一種式(I)化合物與至少一種發磷光之發射體的 混合物包含以發射體與基質材料的整體混合物爲基準計介 於1與99重量%之間的至少一種發磷光之發射體,較佳 地介於2與90重量%之間,特佳地介於3與40重量%之 間,特別地介於5與1 5重量%之間。相應地’混合物包 含以發射體與基質材料的整體混合物爲基準計介於99與 1重量%之間的至少一種式(I)之基質材料,較佳地介於98 與1 〇重量%之間,特佳地介於97與60重量%之間’特別 -38- 200946635 地介於95與85重量%之間。除了式(I)之基質材料以外, 整體混合物亦可包含更多的基質材料。 ' 更優先選擇一種有機電致發光裝置’其特徵在於一或 • 多層係以昇華法的方式塗覆,其中將材料在真空昇華單位 中在低於10·5毫巴之壓力下蒸氣沉積,較佳地低於10·6 毫巴。 同樣地優先選擇一種有機電致發光裝置,其特徵在於 〇 一或多層係以OVPD (有機蒸氣相沉積)法的方式或以載 劑-氣體昇華的輔助方式塗覆,其中將材料在介於10·5 毫巴與1巴之間的壓力下塗覆。該方法的特殊例子爲 OVJP (有機蒸氣噴射印刷)法,其中將材料經由噴嘴直 接塗覆及因此結構化(例如,M. S. Arnold等人之Appl. Phys. Lett. 2008,92,05 3 3 0 1 ) ° 更優先選擇一種有機電致發光裝置,其特徵在於一或 多層係藉由例如旋轉塗佈或以任何所欲之印刷法的方式從 © 溶液製造,該印刷法爲例如網板印刷、橡皮版印刷或套版 印刷,但是特佳爲LITI (光誘致熱成像,熱轉移印刷) 或噴墨印刷。可溶性化合物爲該目的所必要的。 該等方法通常爲熟習本技藝者已知且可由其應用於包 含式(I)化合物及三重態發射體之根據本發明的系統而沒 有問題。 式(I)化合物在有機電致發光裝置中使用時具有下列 超越先前技藝的驚人優點: 1 ·與B-Alq及其他的鋁錯合物相比,操作電壓在使用 -39- 200946635 式(I)化合物時降低相當多,其造成明顯更高的#^ 效 能。 2·在使用式(I)化合物作爲三重態基質材料時,裝· 壽命亦有改進。 3·此外,在使用式(I)化合物作爲三重態基質材料時, 裝置的效能亦有改進。 4.式(I)化合物具有比根據先前技藝常被用作三重態、基 質材料的CBP明顯更高的玻璃轉換溫度。 & 該等上述優點不會隨著發生其他的電子性質的損傷。 本發明藉由下列的實例有更詳細解釋,而不想藉此限 制本發明。 【實施方式】 實例: 下列的合成係在保護性氣體環境下於無水溶劑中進 行’除非另有指示。原料可購自ALDRICH或從文獻已知 © 的方法製備。從2,2’·二硝基聯苯合成2,2,-二胺基聯苯係 根據在 Chem. Commun. 2005,46,5 799-5 80 1 中所敘述之 、 方法進行。4,4’-二溴_2,2’-二硝基聯苯的合成敘述在J.
Am. Chem. Soc. 2006,128,9034-903 5 中。2-锍基苯甲醛 的合成敘述在 Synlett 200 1, 1 956- 1 95 8 中。 實例1 : 3’,2”-二胺一對—四聯苯的合成 a)3’,2”_二硝一對—四聯苯的製備 -40- 200946635
將2.4公克(2.1毫莫耳)Pd(PPh3)4加入在300毫升 水與300毫升THF之混合物中的18.8公克(154.5毫莫 耳)苯基硼酸、30公克(74·6毫莫耳)2,5-二溴基硝苯及 53公克(212.7毫莫耳)碳酸鉀的完全攪拌之脫氣懸浮液 中,並將混合物在回流下加熱2 0小時。在冷卻之後,將 有機相分離’以200毫升水清洗三次及以200毫升氯化鈉 飽和溶液清洗一次,經硫酸鎂乾燥及在旋轉蒸發器中的真 空中蒸發至乾燥。將灰色殘餘物從己烷再結晶。將沉積之 晶體以抽氣過濾,以少量MeOH清洗及在真空中乾燥;產 率:23公克,80%之理論値;純度:根據 HPLC的 99.2%。 b)3’,2”-二胺—對一四聯苯的製備
將16.6公克(42毫莫耳)3’,2”-二硝一對一四聯苯 及1.99公克Pd/C(10。/。)懸浮在200毫升甲醇中及在〇°C 下以攪拌分批加入8.4公克(222毫莫耳)硼氫化鈉。在 攪拌2小時之後’將澄清溶液以稀釋的HC1中和。接著移 -41 - 200946635 除溶劑,並將殘餘物以水極力清洗及從二噁烷再結晶。將 沉澱物過濾及在真空中乾燥’得到11公克(35.6毫莫 耳)結晶固體。總產率爲78% ° 實例2:金屬錯合物的通用合成程序 有兩種製備錯合物的通用方法: A) 芳香族胺與金屬鹽及鄰-羥基醛或鄰一羥基酮的反 應; ❹ B) 芳香族胺的希夫鹼與金屬鹽的反應。 如果副產物(H20 )不破壞所製備之錯合物,則可以 使用方法A。如果該錯合物具有水份敏感性或如果亞胺形 成作用不具定量性,則方法B是適合的。
將260毫莫耳鄰-羥基醛或鄰—羥基酮加入在1〇〇〇 毫升無水甲醇及100毫升三乙胺中的121毫莫耳芳香族二 胺的溶液中。接著將127毫莫耳金屬鹽(例如,乙酸鋅) 加入混合物中’將其在室溫下攪拌24小時,接著過濾及 以冷甲醇清洗。將產物以再結晶純化。 -42- 200946635
i)配位基的合成 配位基的合成係使用移除所形成之水的共沸蒸餾來進 行。將300毫升無水甲苯在具有三頸燒瓶、攪拌器、內溫 度計及滴液漏斗的蒸餾裝置中加熱至沸騰。接著緩慢地逐 滴加入在50毫升無水甲苯中的60毫莫耳芳香族胺之溶液 及在50毫升甲苯中的120毫莫耳醛或酮之溶液。將催化 量之對一甲苯磺酸加入混合物中。進行蒸餾,直到出現澄 清的冷凝甲苯爲止。將溶劑殘餘物在油幫浦真空中(1 3 0 帕斯卡)移除。分離出成爲黃色固體的偶氮甲鹼,從甲苯 再結晶及以MeOH清洗。 Π)錯合物的合成 將在100毫升甲醇中的相應之亞胺配位基(17毫莫 耳)的溶液加入在1〇〇毫升甲醇中的19毫莫耳適合的金 屬鹽(例如,3.4公克乙酸鋅二水合物)之溶液中,並將 混合物在室溫下攪拌3天。在過濾之後,將固體在真空中 乾燥及接著在保護性氣體下再結晶。 -43- 200946635
[[2,2’-[[1,1,-聯苯]-2,2’-二基雙(氮基次甲基)]雙[苯 酚]](2-)-N,N’,0,0’]鋅的合成第一次由 Journal of the Chemical Society, Dalton Transactions; Inorganic Chemistry 1 996, 283 5-28 3 8中的方法(B)敘述。以該方法 所獲得的錯合物含有自由配位基作爲副產物,其使得純度 >99 %之錯合物的製備更困難。從在400毫升純MeOH中 的8.9公克(48毫莫耳)2,2’-二胺基聯苯、17公克(140 毫莫耳)2-羥基苯甲醛、8.8公克(48毫莫耳)乙酸鋅二 水合物及40毫升三乙胺開始的上述方法(A)得到具有非常 高產率及純度> 99.9%之錯合物。在24小時之後,將沉澱 之固體以冷甲醇清洗,在真空中乾燥及接著在保護性氣體 Ο 下從純EtOH再結晶,得到21.5公克(47毫莫耳)結晶 固體。總產率爲 98% ( Tg=152.(TC,Tm = 280_0°C ) 。 · 實例4 : Zn錯合物(22)的合成
-44- 200946635 該錯合物係以從在400毫升純MeOH中的8.9公克 (48毫莫耳)2,2’-二胺基聯苯、24.3公克(140毫莫 耳)3,4-二—第三丁基-2-羥基苯甲醛、8.8公克(48毫莫 -耳)乙酸鋅二水合物及40毫升三乙胺開始的方法(A)合 成。在24小時之後,將沉澱之固體以冷甲醇清洗,在真 空中乾燥及接著在保護性氣體下從純EtOH再結晶,得到 29公克(42毫莫耳)結晶固體。總產率爲 96% ❹ (Tg=170.5°C,Tm = 3 14.2°C )。 實例5 : Zn錯合物(16)的合成
φ 該錯合物係以從在400毫升純MeOH中的16公克 ' (48毫莫耳)3’,2”-二胺-對一四聯苯、24.3公克(140 - 毫莫耳)2-羥基苯甲醛、8.8公克(48毫莫耳)乙酸鋅二 水合物及40毫升三乙胺開始的方法(A)合成。在24小時 之後,將沉澱之固體以冷甲醇清洗,在真空中乾燥及接著 在保護性氣體下從純EtOH再結晶,得到27公克(44毫 莫耳)結晶固體。總產率爲96% ( Tg = 252.7°C,Tm = 367.6 °C )。 實例6 : Zn錯合物(2)的合成 -45- 200946635
該錯合物係以方法(B)合成。 a) 配位基的合成 該合成係從在400毫升甲苯中的11.16公克(60.59 毫莫耳)2,,2’-二胺基聯苯、16.3公克(120毫莫耳)2- © 羥基乙醯苯及0.2公克(1.1毫莫耳)對一甲苯磺酸來進 行。在24小時之後,將沉澱之固體以冷甲醇清洗,得到 2〇公克(47毫莫耳)結晶固體。總產率爲76%。 b) 錯合物的合成
該合成係從在200毫升甲醇中的3.4公克(19毫莫 耳)乙酸鋅二水合物及6公克(17毫莫耳)配位基來進 行。在24小時之後,將沉澱之固體以冷甲醇清洗,在真 G 空中乾燥及接著在保護性氣體下從純EtOH再結晶,得到 6公克(13.1毫莫耳)結晶固體。總產率爲 86% (Tg=l43.4〇C,Tm = 261.〇〇C )。 實例7 : Zn錯合物(15)的合成
-46' 200946635 該錯合物係以方法(B)合成。 ' a)配位基的合成 該合成係從在400毫升甲苯中的1 1.16公克(60.59 毫莫耳)2,2’-二胺基聯苯、23公克(120毫莫耳)2_翔基 —本基酮及〇·2公克(1.1毫旲耳)對-甲.苯擴酸來進 行。在24小時之後,將沉澱之固體以冷甲醇清洗,得到 Ο 22.5公克(41毫莫耳)結晶固體。總產率爲70%。 b)錯合物的合成 該合成係從在200毫升甲醇中的3.4公克(19毫莫 耳)乙酸鋅二水合物及9.2公克(17毫莫耳)配位基來進 行。在24小時之後,將沉澱之固體以冷甲醇清洗,在真 空中乾燥及接著在保護性氣體下從純EtOH再結晶,得到 7-5公克(11毫莫耳)結晶固體。總產率爲 73% © ( Tg = 232.8°C,Tm = 3 54.5 °C )。 實例8 : Zn錯合物(134)的合成
該錯合物係以從在400毫升純MeOH中的8·9公克 (48毫莫耳)2,2,-二胺基聯苯、19.3公克(14〇毫莫 -47- 200946635 耳)2-锍基苯甲醛、8.8公克(48毫莫耳)乙酸鋅二水合 物及40毫升三乙胺開始的方法(A)合成。在24小時之 後,將沉澱之固體以冷甲醇清洗,在真空中乾燥及接著在 保護性氣體下從純EtOH再結晶,得到22公克(45毫莫 耳)結晶固體。總產率爲94% ( Tg= 165.5 °C ,1^ = 290.0 °C )。 實例9至11 :含有式(I)化合物的有機電致發光裝置 ◎ 的製造及特徵 根據本發明的有機電致發光裝置可如在例如 WO 05/003253中的敘述而製造。在此比較各種OLED的結 果。爲了更具比較性,其基本結構、所使用的材料、摻雜 程度及層厚度相同。僅改變在發射層中的主體。第一個裝 置實例敘述根據先前技藝的比較標準,其中發射層由主體 材料B-Alq及客體材料(摻雜劑)Ir(piq)3所組成。此 外,敘述由主體材料Zn錯合物(1)及客體材料(摻雜劑) ◎
Ir(piq)3所組成之具有發射體層的0LED。以類似於上述 的通用方法製造具有下列結構的0LED : 電洞注射層(HIL) 10奈米2,2’,7,7’-肆(二—對-甲 苯胺基)螺旋-9,9’-二芴 電洞傳輸層(HTL) 30奈米NPB(N-萘基-N-苯基_4,4’- 二胺基聯苯) 發射層(EML) 主體:B-Alq(以蒸氣沉積;來自 E-Ray且以昇華兩次進一步純化; -48- 200946635 以雙(2 -甲基-8-羥基喹啉-Nl,08)-(1,1’_聯苯·4-酚)鋁)或CBP(雙(咔 唑-9-基)聯苯)作爲比較或Ζη錯合 ’物(1) 〇 摻雜劑:Ir(piq)3(10°/。摻雜,以蒸 氣沉積;根據WO 03/0068526合 成)。 ® 電子導體(ETL) 20奈米A1Q3(購自E-Ray,參(經 基喹啉)鋁(III))。 陰極 1奈米LiF,在頂端上的150奈米 A1。 爲了清楚起見,將Ir(piq)3的結構顯示於下:
這些尙未最優化之OLED係以標準方法特徵化;就該 目的而言’測定電致發光光譜、從電流/電壓/發光強度特 徵線(IUL特徵線)所計算以發光強度函數表示的效能 (以cd/A測量)及壽命。 以主體CBP所製造之OLED作爲比較實驗,在上述 條件下典型地獲得約6.5 cd/A之最大效能,具有CIE之 -49- 200946635 色彩坐標:χ = 〇·68,y = 〇_32。就1 000 cd/平方公尺之參考 用發光密度而言,需要6.8 V之電壓。在1〇〇〇 cd/平方公 尺之初發光密度下的壽命約6000小時(參見表1 )。 以主體B-Alq所製造之OLED作爲另一比較實驗,在 上述條件下典型地獲得約8_0 cd/A之最大效能,具有ciE 之色彩坐標:χ = 〇·68’ y = 0.32。就1000 cd/平方公尺之參 考用發光密度而言,需要7.5 V之電壓。在1〇〇〇 cd/平方 公尺之初發光密度下的壽命約7000小時(參見表1 )。 對照之下,以主體Zn錯合物(1)所製造之根據本發明 的OLED展現8.5 cd/A之最大效能,具有ciE之色彩坐 標:x = 0.68’ y = 0.32’具有其他相同的結構,就i〇〇〇 cd/ 平方公尺之參考用發光密度而言,必要的電壓爲5.0 V (參見表1)。在1〇〇〇 cd/平方公尺之初發光密度下的壽 命爲9000小時,其明顯比較長,且在5.0 V之電壓明顯 低於參考材料CBP及B-Alq的例子(參見表。 表1 :具有各種主體 才料及以Ir(Piq),作爲j _雜劑的裝置結果 實驗 EML 最大 纖 [cd/Al 在1000 cd/平方 公尺下的電壓 rvi CIE (x,y) 壽命[小時] 初發光強度 1000[cd/平方 實例9 (比較) CBP : 10% 之 Ir_3 (40奈米) 6.5 6.8 0.68/ 0.32 6000 實例10 (比較) BAlq : 10%之 Ir(piq)3 (40奈米) 8.0 7.5 0.68/ 0.32 7000 實例11 Zn錯合物⑴: 10% 之 Ir(piq>3 (40奈米) 8.5 5.0 0.68/ 0.32 9000
Claims (1)
- 200946635 十、申請專利範圍 h一種有機電致發光裝置,其包含在發射層中的至少 一種發磷光化合物及至少一種式(I)化合物:Ο 式(I) 其中下述適用於所使用的符號及下標: Μ 在各次出現係相同或不同地爲具有氧化態+ΙΙ的 金屬離子,其係選自 Be、Mg、Ca、Sr、Ba、 Fe、Ru、Os、Co、Ni、Pd、Cu、Zn、Cd、Hg、 Sn 及 Pb ; X 在各次出現係相同或不同地爲0、S或CO-O ; Ar1爲具有5至60個芳香族環原子之芳香族或雜芳 香族環系統,其可被一或多個R基取代且其中 各個芳香族基團可經由具有1至10個C原子之 伸烷基互相連結,另外,其中一或多個未鄰接之 C原子可被0或S替換; Ar2在各次出現係相同或不同地爲具有5至60個芳 香族環原子之芳香族或雜芳香族環系統,其可被 一或多個R基取代; Y 在各次出現係相同或不同地爲單鍵或具有1至 -51 - 200946635 ι〇個c原子之伸烷基,另外,其中未與氮鍵結 的一或多個未鄰接之c原子可被0替換且可被 一或多個R基取代; · R 在各次出現係相同或不同地爲Η、F、Cl、Br、 I、N(R2)2、CN、N〇2、Si(R2)3、B(〇R2)2、 C( = 0)R2、P( = 0)(R2)2、S( = 0)R2、S( = 〇)2R2、 0S02R2、具有1至40個C原子之直鏈烷基、烷 氧基或硫烷基或具有3至40個C原子之分枝或 0 環狀烷基、烷氧基或硫烷基,每個該等基團可被 一或多個R2基取代,其中一或多個未鄰接之 CH2 基團可被 R2C = CR2、C e C、Si(R2)2、 Ge(R2)2、Sn(R2)2、C = 0、C = S、C = Se、C = NR2、 P( = 0)(R2)、SO、S02、NR2、O、S 或 CONR2 替 換,且其中一或多個 H原子可被F、Cl、Br、 I、CN或N〇2替換,或爲具有5至60個芳香族 環原子之芳香族或雜芳香族環系統,每個該等基 © 團可被一或多個R2基取代,或爲具有5至60個 芳香族環原子之芳氧基或雜芳氧基,其可被一或 ' 多個R2基取代,或爲該等系統之組合;二或多 個取代基R在此亦可互相形成單-或多環脂肪 族或芳香族環系統; R1 在各次出現係相同或不同地爲Η、F、CF3、具有 1至40個C原子之直鏈烷基或具有3至40個C 原子之分枝或環狀烷基,每個該等基團可被一或 -52- 200946635 多個R2基取代,其中一或多個未鄰接之(:仏基 團可被 R2C = CR2、C Ξ C、Si(R2)2、Ge(R2)2、 ^ Sn(R2)2替換,且其中一或多個Η原子可被F、 - Cl、Br、I、CN或N〇2替換,或爲具有5至6〇 個芳香族環原子之芳香族或雜芳香族環系統,每 個該等基團可被一或多個R2基取代,或爲該等 系統之組合;R1在此亦可與一或多個取代基R 〇 形成單-或多環脂肪族或芳香族環系統; R2 在各次出現係相同或不同地爲H、F或具有1至 2〇個C原子之脂肪族、芳香族或雜芳香族經 基,另外,其中一或多個Η原子可被F替換; 二或多個取代基R2在此亦可互相形成單-或多 環脂肪族或芳香族環系統; η 在各次出現係相同或不同地爲0、1或2。 2.根據申請專利範圍第1項之有機電致發光裝置,其 〇 中’符號γ在各次出現係相同或不同地代表單鍵或c(r)2 ' 基團。 3·根據申請專利範圍第1或2項之有機電致發光裝 置’其中’就n = 〇之基團γ-Αι^-γ代表式(π)至(χν)之基 團’其中虛線鍵表示與亞胺氮之連結: -53- 200946635(XV)4.根據申請專利範圍第1或2項之有機電致發光裝 置,其中,就n=l之符號 Ar1代表式(XVI)至(XXI)之基 團,其中虛線鍵表示與亞胺氮之連結:5.根據申請專利範圍第1或2項之有機電致發光裝 置,其中,符號Ar2在各次出現係相同或不同地代表具有 5至16個芳香族環原子之芳基或雜芳基’其可被一或多 個R基取代,特別是選自苯基、1-或2_萘基、4_聯苯基、 -54- 200946635 1-或2-蒽基,2-或3-噻吩基、2-或3-吡咯基、2-或3-呋喃 基、2-、3-或4-吡啶基、3-或4-嗒畊基、4-或5-嘧啶基、 '耻哄基-、2-、3-、4-、5-、6-、7 -或 8 -喹啉基或 3-、4-、 - 5-、6-、7-或8-異喹啉基,每個該等基團可被一或多個R 基取代。 6.根據申請專利範圍第1或2項之有機電致發光裝 置,其中,符號R在各次出現係相同或不同地代表F、 0 n(r2)2、Si(R2)3、C( = 0)R2、P( = 〇)(R2)2、具有 1 至 10 個 C原子之直鏈烷基或具有3至10個C原子之分枝或環狀 烷基,每個該等基團可被一或多個R2基取代,其中一或 多個未鄰接之CH2基團可被R2C = CR2-、Ο或S替換,且 一或多個Η原子可被F替換,或爲具有5至16個芳香族 環原子之芳基或雜芳基,每個該等基團可被一或多個R2 基取代,或該等系統之組合;二或多個取代基R在此亦可 互相形成單-或多環脂肪族或芳香族環系統。 Ο 7.根據申請專利範圍第1或2項之有機電致發光裝 置’其中’符號R1在各次出現係相同或不同地代表Η、 " 具有1至6個C原子之直鏈烷基或具有3至6個C原子 之分枝或環狀烷基,其中在每個例子中的一或多個Η原 子亦可被F替換,或爲具有5至16個芳香族環原子之芳 基或雜芳基,每個該等基團可被一或多個R2基取代。 8.根據申請專利範圍第1或2項之有機電致發光裝 置’其中’該式(I)化合物爲簡單的錯合物形式或爲呈固 態的二聚物或寡聚物形式。 -55- 200946635 9. 根據申請專利範圍第1或2項之有機電致發光裝 置,其中,該式(I)化合物中的所有符號Ar2是相同的,所 有符號X是相同的所有符號R1是相同的,所有符號Υ 是相同的,且該化合物被同樣地取代。 10. 根據申請專利範圍第1或2項之有機電致發光裝 置,其中,該裝置包含陰極、陽極及至少一個發射層,且 可選擇地包含更多選自電洞注射層、電洞傳輸層、電子阻 斷層、電洞阻斷層、電子傳輸層、電子注射層、電荷產生 層及有機或無機ρ/η接面之層。 1 1 .根據申請專利範圍第1或2項之有機電致發光裝 置,其中,該有機電致發光裝置包含數個發射層,其中至 少一層包含至少一種式(I)化合物及至少一種發磷光化合 物。 12. 根據申請專利範圍第1或2項之有機電致發光裝 置,其中,該發磷光化合物含有銅、鉬、鎢、銶、釕、 餓、鍺、銥、鈀、鈾、銀、金或銪。 13. 根據申請專利範圍第12項之有機電致發光裝置, 其中’該發磷光化合物包含至少一種式(XXII)至(XXV)化 合物:(XXII)(XXIII)200946635 其中R具有與申請專利範圍第1項所定義之相 義,且下述適用於所使用的其他符號: _ DCy在各次出現係相同或不同地爲環狀基團,其#胃 •至少一個施體原子,較佳爲氮或磷,該環狀ggj 經由其與金屬鍵結,且其可依次攜帶一或多個取 代基R ;基團DCy及CCy可經由共價鍵互相連 接; 〇 CCy在各次出現係相同或不同地爲環狀基團,其含有 碳原子,該環狀基團經由其與金屬鍵結,且其可 依次攜帶一或多個取代基R; A 在各次出現係相同或不同地爲單陰離子、雙牙螯 合配位基,較佳爲二酮根(diketonate)配位基。 14. 一種製造根據申請專利範圍第1項之有機電致發 光裝置的方法,其特徵在於一或多層係以昇華法的方式或 以0VPD (有機蒸氣相沉積)法的方式或以0VJP (有機 © 蒸氣噴射印刷)法的方式或以載劑-氣體昇華的輔助方式 * 塗覆,或藉由旋轉塗佈或以印刷法的方式從溶液製造。 ' 15.—種根據申請專利範圍第1項之式(I)化合物的用 途,其作爲在有機電致發光裝置中的發磷光化合物的基質 材料。 -57- 200946635 七、指定代表圖·· (一) 、本案指定代表圖為:無 (二) 、本代表圖之元件代表符號簡單說明:無 Ο 八、本案若有化學式時,請揭示最能顯示發明特徵的化學 式:式I式①-4-
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-
2007
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2008
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- 2008-10-14 JP JP2010533453A patent/JP5591710B2/ja not_active Expired - Fee Related
- 2008-10-14 EP EP08802877A patent/EP2207864A1/de not_active Withdrawn
- 2008-10-14 CN CN200880115344.XA patent/CN101878279B/zh not_active Expired - Fee Related
- 2008-10-14 US US12/742,549 patent/US8487300B2/en not_active Expired - Fee Related
- 2008-11-07 TW TW097143149A patent/TW200946635A/zh unknown
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KR101571178B1 (ko) | 2015-11-23 |
JP5591710B2 (ja) | 2014-09-17 |
US20100244009A1 (en) | 2010-09-30 |
WO2009062578A1 (de) | 2009-05-22 |
KR20100096162A (ko) | 2010-09-01 |
DE102007053771A1 (de) | 2009-05-14 |
JP2011503886A (ja) | 2011-01-27 |
CN101878279A (zh) | 2010-11-03 |
CN101878279B (zh) | 2016-05-11 |
EP2207864A1 (de) | 2010-07-21 |
US8487300B2 (en) | 2013-07-16 |
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