TWI267544B - Electroluminescent materials - Google Patents
Electroluminescent materials Download PDFInfo
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- C09K2211/1018—Heterocyclic compounds
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Description
1267544 玖、發辦氛男 (發明說明麟明:發贿屬之技術賴、先前麟、料、實施方歧圖式簡單說明) 技術領域 本發明有關發光材料,其可藉由真空沈積而沈積成薄 層’且可於有機發光裝置(OLEDs)中作為沒有的摻雜劑。 先前技術 在過去20年内,發光二極體(LED)的發展主要著眼於無 機類型’係由於早期開發的有機發光裝置(0LEDS)導致不 良裝配及封裝,且壽命短之故。現在,在市面上提供以砰 化鎵為王的LEDs,其在某些光譜區的功效超過傳統的過濾 螢光燈。然而,在用於顯示器技術的發光材料開發中,無 機半導體材料不適宜大面積裝配之顯示器。 I960年代,P0pe等在紐約大學證明了以蒽材料為主的有 機電激發光(J. C/^所. 38, 2042,(1963))。自從 C· w· Tang 等(办〆户/^· z州.51,913,( 1987))在柯達(K〇dak)發現了基§ 於三(8-羥基醌化)銘(aw)的薄膜裝置,有機電激發光材料 已取得了很大進展。其大多歸功於不斷有新的和改良的電 激發光材料發現。從小的螢光分子到共輛之高分子,許多 OLEDs已顯示可展現足夠亮|、顯著功效、良好操作壽命 和所需之發光顏色範圍。 由於金屬錯合物之不尋常化學和電子性質,因此含有金 屬錯合物的有機發光裝置特別受到曝目。一些帶有重金屬 的化合物,由於其高的内量子效率而顯現出應用於沉腦 的潛在優勢。#統上’使用勞光材料作為發光主體(h〇sts) 的摻雜劑。按照_er機制,$穴和電子重組後形成單 84298-950510.doc
1267544 態激子(最大理論内量予效率=25%),藉由偶極-偶極相互 作用發出電激發光(美國專利6,31〇,36〇)。然而,對於重金 屬錯合物,強的自旋-執遒耦合可導致單態-三重態混合, 這會引起OLEDs中的高效電激發光(理論内量子效率高達 l00%)(Nature, 395, 151? ( 1998); Synthetic Metals, 93, 245, ( 1998);却;7/.尸/^· Ze". 77,904,(2000))。 然而’一些磷光材料有本質上的缺陷,例如由於過長的 壽命以及三重態·三重態消滅導致的發光位置(emissi〇n sites)飽和,以及在高摻雜量之下由於分子間相互作用增 強導致的濃度淬熄〇01^11加以011911611(^1^)(户/^.;^.5· 60, 14422, (1999))。 例如’在有機發光裝置中,使用四配位體的偶氮曱川-鋅錯合物作為藍色光發射體,其最大亮度僅約為1〇〇〇 cd/m2 (Jpn, 乂却尸/^·, 32, L5 11 (1993);美國專利 5,432,014) 〇 在OLEDs中’已使用偶氮甲川-鋁/鎵錯合物作為發光材 料。含有偶氮甲川-鎵錯合物的裝置在1〇 V時的電流密度 為1 mA/cm2,且電發出的光是呈綠色的藍光(美國專利 6,316,130) 〇 因此需要開發一種可實現OLEDs中基質和摻雜劑間能 量有效轉移的發光摻雜劑材料,同時在足夠高摻雜濃度 時,這些材料不會或很少自我淬熄(self_quenching)。 發明内容 本發明具體實施例中’其目的實例包括: 本發明之王要目的係製備接雜新穎發光材料的有機發 8429S-950510.doc (3) 1267544 展現低啟動電壓(turn-on 光裝置(OLEDs)。該裳置 voltages)、兩亮度和高效率。 本發明一目的係提供可藉沐 … 精/飞相/儿積万法沉積成已知厚 度的薄層的熱穩定、防潮的金屬_螯合材料。 再者,本發明有關高亮度接雜劑的設計,其可以低濃度 量使用在發光裝置中。 四配位體ONNO-型配 製備如式I和式Π所示之衍生
及第10族金屬(包括銷)的新穎發光材料
Α II 其中Μ代表第10族金屬(包括鉑),Ri_Ri4各獨立選自由 氫、_素、烷基、經取代烷基、芳基、經取代芳基所成之 組群,該取代基係選自_素、低碳烷基以及辨識之供體和 受體基團。 本發明之具體實施例包括(但不限於)包含用以產生電 激發光的異質結構的OLEDs,其含有陽極(IT0玻璃物質)、 2穴傳送層(ΝΡΒ( α -莕基苯基聯苯基胺、基質發光層[主 體材料(具有不同濃度的如本文式I和式π所示的掺雜劑 的雙(2-(2’-經基苯基)吡啶鈹)(Bepp2))] ’電荷轉移層(氟化 鐘)和陰極(銘金屬)。 本文中’於OLEDs中作為有效掺雜劑之較佳具體實施例 84298-950510.doc
1267544 (4)
本發明提供一種可於電激發光裝置中作為發光摻雜劑 的新穎材料。本發明包括該等新穎錯合物的合成方法以及 其作為發光材料的用途。本發明的裝置可應用在顯示器、 發光體、信號燈的顯示板或液晶顯示器的光源等領域。 實施方式 本發明主要有關一種新穎發光材料的合成、光譜特徵鑒 定、磷光、發光性質以及其在OLEDs上的應用。實施例的 提出有助於理解本發明,但非用以且不應該被認為用於以 任何方式限制後述申請專利範圍中闡述的本發明範圍。 所提供之實施例說明配體la和2a以及鉑錯合物lb和2b 的合成方法。藉由文獻製程(厂<1:1^111.8〇(:.,?6^111^&113· 2,863,( 1998))之改良方法,製備四配位體ONNO-型配體la 和2a。製備ONNO-型配體之另一實施例已有報導(美國專利 6,177,419)。 實施例1 la的合成 84298-950510.doc 1267544 (5)
使6,6,·雙(2-甲氧基苯基)-4,4’-雙(第三丁基)-2,2’-聯吡 啶(1克)之氫溴酸(47%,20毫升)混合液回流12小時。冷卻 到室溫,以飽和Na2C03水溶液在室溫下中和。該有機產物 以氯仿萃取,且萃取液以去離子水洗滌(50毫升x2),以無 水Na2S04乾燥,除去溶劑得到固體殘留物。自甲醇/二氯甲 烷溶液中再結晶,獲得la的結晶產物。 EI-MS (m/z): 452 [M] + . lH NMR (CDC13, δ5 ppm): 14.45 (2H, s5 OH),8.16 (2H,d,J=1.4 Hz,ArH),7·97 (2H,d,J=1.3 Hz,AirH),7.90 (2H,dd,J=8,0 Hz,J=1.4 Hz,ArH),7.34 (2H,td,J=8.4 Hz,J=1.5 Hz, ArH),7.07 (2H,dd,J=8.2 Hz,J=1.6 Hz,ArH),6·96 (2H,td,J=8.1 Hz,J=1.2 Hz,ArH),1.47 (18H,s,ιΒιι)· 13C NMR (CDC13, δ,ppm): 163.3, 159.7, 157.5, 152.2, 131.5, 126.5, 119.2, 118.9, 118.4, 116.4, 35.6, 30.6 〇 實施例2 1 b的合成
描述金屬錯合物lb的合成方法。將NaOMe (0.014克,0.25 毫莫耳)和配體la(0. 113克,0.25毫莫耳)之甲醇(20毫升)混 84298-950510.doc
1267544 ⑹ 合液攪拌2小時。於該甲醇懸浮液中添加Pt(CH3CN)2Cl2 (0· 25毫莫耳)之乙腈溶液(20毫升),並回流24小時。所得懸 浮液過濾並濃縮到約5毫升。加入乙醚後得到黃褐色的固 體。粗產物藉由使乙醚擴散到二氯甲烷溶液中而再結晶, 獲得黃色結晶。FAB-MS (m/z): 645 [M] +,1292 (2M+ + 2),1938 (3M+ + 3) 〇 4 NMR (CDC13,δ,ppm): 8.32 (d,2Η,J=1.41 Hz
ArH),8·01 (d,2H,J=7.25 Hz,ArH),7.85 (d,2H,J=1.68 Hz, ArH),7.48 (dd,2H,J=7_38 Hz,J=1.13 Hz,ArH),7.38 (td,2H, J=5.35,1.61 Hz,ArH),6.79 (td,2H,J=5.40,1.35 Hz,ArH), 1.54 (s,18H,"Bu)。13C NMR (CDC13, δ,ppm): 162.745,159. 105, 155.291, 149.851, 131.269, 128.005, 124.060, 120.465, 120.402, 116.302,116.148,30.402,29.715,FTIR (KBr,cnT1): 3086 w, 2953 m,1612 w,1528 s,1351 s,1034 m,885 w,723 m。 實施例3 2a的合成
於裝配有回流冷凝管的100毫升圓底燒瓶中,混合2,9-雙Ο甲氧基苯基)·4,7·二苯基-1,10-繞菲啉(細研磨,2克, 3.7毫莫耳)及鹽酸吡啶鹽(4.23克,37毫莫耳)。在氮氣流下 使混合物加熱至210°C歷時36小時。冷卻後加水(30毫升), 84298-950510.doc -10-
1267544 且水溶液以氯仿萃取(3x30毫升)。合併的有機萃取液以飽 和碳酸氫鈉溶液(5x30毫升)和水(3x3〇毫升)洗滌,以無水硫 酸鎂乾燥,蒸發後得到亮黃色固體。經矽膠層析,使用正 己烷:二氣甲烷(1:2)作為溶離液,獲得ο.”克黃色固體。 FAB-MS (m/z): 517 [M+H]+。4 NMR (300 MHz,CDC13,δ, ppm): 14.69 (2Η,s,ΟΗ),8·52 (2Η,s,ArH),8·41 (2Η,dd, J=8.0,1·3 Hz,ArH),7·90 (2H,s,ArH),7.71 (4H,d, J=7.4 Hz), 7.64 (6H,m,ArH),7.43 (2H,td5 J=7.7,ι·5 Hz,ArH),7.10 (2H, dd,J=7.4 Hz, 1.3 Hz,ArH),7.04 (2H,td,J=7.5,1.3 Hz,ArH)。 13C NMR (600 MHz,CDC13): δ=160·5,157.7,150.3,142·8, 137.8, 132.2, 129.6, 128.9, 128·8, 127.1, 125.7, 123.7, 120.6, 119.4, 119.2, 118.9 。 复立例4 2b的合成
使K2PtCl4(〇.08克’ 〇]9毫莫耳)和克,0.19毫莫耳 在冰醋酸(10毫升)中回流2天。冷卻後,過濾收集所產生 的懸浮液,以乙酸和水依序洗條,然後真空乾燥,獲得褐 色固體。粗產物經矽膠管枝屏士 C &枉層析純化,以二氯甲烷作為% 離液。緩慢蒸發二氣甲檢、发读 ...y/ 乳T砭/合履,使產物再結晶,獲得紅色 結晶。FAB-MS: m/z. ?1〇 [m+h]+。1h 麵^ (謂 MHz 84298-950510.doc ⑻ 1267544 DMSO-d6) 8·81 (2H,s,ArH),8·56 (2H,d,J=8.9 Hz,ArH),8.01 (2H,s,ArH),7·86 (4H,m,ArH),7·71 (6H,dd,J = 4.9,2.0 Hz,Ai:H),7.44 (2H,t,J=7.4 Hz,ArH),7·24 (2H,d,J=8.2 Hz, ArH),6.80 (2H,t,J=7.6 Hz,ArH) 〇 本發明的舶錯合物lb和2b的光譜特徵如表1所示。對於 錯合物lb,在250-350 nm觀察到強吸收譜帶(ε = 38400- 17500 dn^morknT1),在Xmax 398 nm觀察到中強度的吸收譜帶 (ε= 10800 dn^morknT1)(圖 1)。此外,在約 480 nm可發現一 個寬吸收譜帶(2800 dn^morkm·1)。對於錯合物2b(圖1),於 CH2C12中,在291-375 nm處觀察到有幾個電子振動躍遷 (ε = 39200至 24700 (Ιπ^ιηοΓ^πΓ1)及在 504 nm處觀察到一個寬 帶(ε = 7200 dn^mor1。!!!·1)。 表1 : lb和2b在CH2CI2中的UV/vis吸收數據 錯合物 λ„1&χ/ηιη(ε/104χάπι3οοΓ1οηι'1) lb 255 (3.80),315 (1.75),400 (0.82),480 (0.25),505 (0.22) 2b 291 (3.92),315 (3.40),325 (3.23),352 (2.58),375 (2.47), 420 (0.52), 488 (0.67), 504 (0.72) 鉑錯合物lb和2b在溶液中以及作成薄膜時的光致發光 (PL)概述於表2。圖2中,錯合物lb在CH2C12中及作成薄膜 時,分別在595 nm和599 nm觀察到298K無結構發射 (structureless emission)。錯合物2b在溶液中及作成薄膜時的 PL性質如圖3所示。與在溶液中比較,作成薄膜的2b的發 射最大值遷移了 1704 cm·1。同時,錯合物lb和2b在CH2C12 中的壽命分別是1·9和5.3 ps,光量子產率分別是〇·ΐ和 0·6(以Ru(bpy)3Cl2為參照標準)。 84298-950510.doc -12- (9) 1267544 表2 :錯合物lb和2b在溶液中和作成薄膜時的PL性質 錯合物(測量介質/溫度) 發射波長(最大值/nm) 壽命(# s) 量子產率 lb(CH2Cl2/298K) 595 1.9 0.1 lb(薄膜/298K) 599 / / 2b(CH2Cl2/298K) 586 5.3 0.6 2b(薄膜/298K) 651 / / 濃度= lXl〇'5mol dm 錯合物lb和2b的TGA溫度記錄圖如圖4所示。兩種錯合物 均證明了在氮氣和空氣中,加熱速度為15°C /分鐘條件下 有高的溫度穩定性。錯合物2b在氮氣中在高達536°C下和 在空氣中379 °C下穩定。lb在氮氣中的起始溫度(on-set temperatures)為438°C,在空氣中為382°C。這些觀測結果顯 示這些發光材料在製備OLEDs時,在真空沈積條件下可以 昇華而且穩定。 在圖5中圖示說明根據本發明的電激發光裝置。作為本 發明的一實施例,製造結構配置如下的OLEDs: ΙΤΟ/ΝΡΒ( α 莕基苯基聯苯基胺)(500 Α)/[0·3 wt% (裝置A),1 wt°/〇(裝置 B),或 2 wt% (裝置 C)的錯合物 lb] : Bepp2 (400 A)/LiF (15 A)/A1 (2000 A)。裝置 A (0.3 wt% 的 lb)的製造如下: 實施例5 裝置A的裝配如下:在玻璃基材上薄層電阻為20Ω/平方 的錮錫氧化物(ITO)電極、厚度500 A的空穴傳送材料 ΝΡΒ( α -莕基苯基聯苯基胺)、由0.3 wt%錯合物lb和藍發光 材料Bepp2(雙(2-(2f-羥基苯基)吡啶鈹)製成的厚度400 A的 發光層、厚度15 A的增強電荷轉移層LiF、及厚度2000 A的 84298-950510.doc -13- 1267544 (ίο) 鋁層。在5 X l〇·6 mbari下依序層壓金屬層和有機層,但不 同真空沉積方法之間不切斷真空。各層沉積速率為每秒2 或5 A。由陽極和陰極重疊區域所界定之装置發射區域為3 X 3 mm2。ITO塗層的玻璃基材以有機溶劑(丙酮·異丙醇甲 醇)、去離子水和紫外線臭氧清洗劑先後清洗。在室溫下, 以分光光度計和電腦控制的直流電源分別測量裝置的EL 光譜和電流密度-電壓-亮度特性。 對於該等實施例,當錯合物113的摻雜濃度量從2 wt%調 整到0.3 wt%時’裝置的外邵效率增加。該特定實施例進 一步說明如下: 复列6 含有0.3 wt%摻雜量錯合物ib的裝置A的性能如圖6所 示。當裝置受前向偏壓驅動時,在453 nm和540 nm觀察到 兩個強的EL發光。圖中亦顯示裝置A的電流密度-電壓-亮 度特徵曲線。啟動電壓約為6- 7 V。裝置最大功率在亮度 2849 cd/m2下為4.1 cd/A。在驅動電壓10 V時達到最大亮度 9325 cd/m2。裝置A的EL顏色為黃色(CIE座標:χ=〇·33, y=0.47) 〇 實施例7 含有1.0 wt%摻雜量錯合物lb的裝置B的性能如圖7所 示。該裝置在546 nm有一個強的EL發光峰,在457 nm有弱 的發光。裝置B的啟動電壓約為6-7 V。效率在亮度1927 cd/m2下為1.9 cd/A,最大亮度在9.5 V驅動電壓時為6563 cd/m2。裝置B的EL顏色為黃色(CIE座標:x=0.39, y=0.54)。 實施例8 84298-950510.doc -14- (ii) 1267544
口有2·〇 Wt/°摻雜量錯合物lb的裝置C在548 nm顯示強EL 發光峰在大约450 nm有非常弱的發光(圖8);檢測到EL 效率為丨·5 Cd/A。在驅動電壓12 V時觀察到亮度6450 cd/m2。 裝置C的EL顏色為黃色(cie座標:x==〇 42,y=0.56)。 典土上’據報導在有機或聚合物發光裝置中高於5%的 摻雜蓋可達到摻雜劑發光。本發明中,當摻雜量約2%時, OLEDs顯示錯合物11}實際上完全發光,當錯合物掺雜量從 2·0 Wt%降到〇·3 wt°/◦時,裝置效率從1.5 cd/A升至4.1 cd/A。 圖式簡單翁_明 圖1錯合物lb及2b在CH2C12中的吸收光譜 圖2錯合物ib在CH2C12中和作成薄膜時在298K下的發射 光譜 圖3錯合物2b在CH2C12中和作成薄膜時在298K下的發射 光譜 圖4在氮氣和空氣下錯合物lb和2b的TGA溫度記錄圖 圖5本發明的〇LED示意圖 圖6含錯合物ib (摻入量0.3 wt%)的裝置A的電激發光光 譜、電流密度-電壓-亮度曲線 圖7含錯合物ib (摻入量1·〇 wt%)的裝置B的電激發光光 譜、電流-電壓-亮度曲線 圖8含錯合物ib(摻入量2.0 wt%)的裝置c的電激發光光 譜 84298-950510.doc -15·
Claims (1)
1267544 拾、申請專利範園 1. 一種於含有用於產生電激發光的異質結構的有機發光 裝置中之發光層,其包含至少一種主體材料及存在於 該主體材料中作為摻雜劑之發光分子,其中該發光分 子係選自帶有四配位體的金屬錯合物,該四配位體含 有至少一個p比淀或經取代P比淀基。 2. 如申請專利範圍第1項之發光層,其中該發光分子係選 自帶有四配位體ONNO-型配體的金屬錯合物,其中NN 為2,2、聯毗啶或經取代之2,2’-聯吡啶或1,10-繞菲啉或 經取代之1,10-繞菲啉。 3. 如申請專利範圍第1項之發光層,其中該金屬錯合物之 金屬係選自第10族金屬。 4. 如申請專利範圍第1項之發光層,其中該發光分子可具 有式I和式Π所示之化學結構:
I II 其中Μ代表第10族金屬(包括鉑),及RKR14各獨立選自 氫、函素、烷基、經取代烷基、芳基、經取代芳基所 成之組群,該取代基係選自函素、低碳烷基以及辨識 之供體和受體基團。 84298-950510.doc 1267544 1 5.如申请專利範圍第4項之發光層,其中該發光分子在卞 主體材料中係存在低濃度作為摻雜劑, 巴栝以王體材 料重量計之〇·3至2 〇重量%。 係產生黃色電激發 6·如申凊專利範圍第4項之發光層 光0 7· 一種轉變由包括如申請專利範圍第5項之發光層之 機發光裝置所發射之顏色(CIE座標)之方法。 8.如申請專利範圍第4項之發光層’其中該主體材 (2-(2f-羥基苯基)p比啶鈹(Β·2)。 9_如申請專利範圍第4項之發光層’其中該主體材料及該 發光分子可藉由昇華或真空沈積或汽相沉積或旋轉:塗 布或其他方法予以沈積成薄層。 10· —種發光分子,係以如申請專利範圍第4項之發光層之 、斤示其中忒Us、反7_化8及R10-Ri4基為質子原子, R6及R9基為第三丁基,且Μ為鉑,亦即
11· 一種發光分子, 式II所示,其中 及R9基為苯基, 係以如申請專利範圍第4項之發光層 R1-R5、117-118及R1(rR14基為質子原子, 且Μ為銘,亦即 84298-950510.doc
1267544 84298-950510.doc 1267544 陸、(一)、本案指定代表圖為:第5圖 (二)、本代表圖之元件代表符號簡單說明: 柒、本案若有化學式時,請揭示最能顯示發明特徵的化學式: 84298-950510.doc
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TWI758070B (zh) * | 2016-06-20 | 2022-03-11 | 美商環球展覽公司 | 有機電致發光材料及裝置 |
TWI813176B (zh) * | 2016-06-20 | 2023-08-21 | 美商環球展覽公司 | 有機電致發光材料及裝置 |
TWI835688B (zh) * | 2016-06-20 | 2024-03-11 | 美商環球展覽公司 | 有機電致發光材料及裝置 |
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CN100509827C (zh) | 2009-07-08 |
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JP2010050451A (ja) | 2010-03-04 |
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EP1499624A4 (en) | 2006-05-03 |
JP4981252B2 (ja) | 2012-07-18 |
TW200427814A (en) | 2004-12-16 |
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