TWI429652B - 有機金屬化合物及包含其之有機電激發光裝置 - Google Patents

有機金屬化合物及包含其之有機電激發光裝置 Download PDF

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TWI429652B
TWI429652B TW100127917A TW100127917A TWI429652B TW I429652 B TWI429652 B TW I429652B TW 100127917 A TW100127917 A TW 100127917A TW 100127917 A TW100127917 A TW 100127917A TW I429652 B TWI429652 B TW I429652B
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Heh Lung Huang
Teng Chih Chao
Hao Chun Lee
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Ind Tech Res Inst
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Description

有機金屬化合物及包含其之有機電激發光裝置
本發明關於一種有機金屬化合物及包含其之有機電激發光裝置，特別關於一種有機金屬磷光化合物及包含其之磷光有機電激發光裝置。
有機電致發光裝置(organic electroluminescent device)，亦稱作有機發光二極體(organic light-emitting diode;OLED)，是以有機層作為主動層的一種發光二極體(LED)。由於有機電致發光裝置具有低電壓操作、高亮度、重量輕、廣視角、以及高對比值等優點，近年來已漸漸使用於平面面板顯示器(flat panel display)上。與液晶顯示器不同，有機電激發光顯示器所包含之有機發光二極體畫素陣列係具有自發光的特性，因此不需外加背光源。
一般而言，有機發光二極體元件包括一對電極，以及在電極之間的一有機發光介質層。發光是導因於以下的現象。當電場施於兩電極時，陰極射出電子到有機發光介質層，陽極射出電洞到有機發光介質層。當電子與電洞在有機發光介質層內結合時，會產生激子(excitons)。電子和電洞的再結合就伴隨著發光。
依據電洞和電子的自旋態(spin state)，由電洞和電子之再結合而產生的激子可具有三重態(triplet)或單重態(singlet)之自旋態。由單重態激子(singlet exciton)所產生的發光為螢光(fluorescence)，而由三重態激子(triplet exciton)所產生的發光為磷光(phosphorescence)。磷光的發光效率是螢光的三倍。因此，發展高效率的磷光材料以增進有機發光二極體元件的發光效率是非常重要的。
不過，傳統紅光有機磷光發光材料的發光效率並不佳，然而製作高CRI白光就必須要用紅光、綠光和藍光等三原色光譜的發光材料，且具有紅光光譜區域的有機發光二極體元件照射傷口時對傷口癒合有幫助。因此，開發出紅位移的有機磷光發光材料，對於有機發光二極體技術而，是一個很重要的課題。
本發明提出一種有機金屬化合物，其化學結構具有4-phenylnaphtho[1,2-b]thiophene基團，可使材料光色達到紅光光譜。本發明所述之有機金屬化合物，可應用在有機電激發光裝置，作為發光單元的材料，提升有機電激發光裝置的元件效率。
根據本發明一較佳實施例，該有機金屬化合物，具有如式(I)或式(II)所示之化學結構：
其中，X係為C-H或是N，Y係為CH2 或是NH；R1 係氫、或C1-8 烷基；以及A1 係乙醯丙酮(acetylacetone)配位基、具有苯環之乙醯丙酮(acetylacetone)配位基、或其衍生物。
根據本發明另一較佳實施例，本發明係提供一種有機電激發光裝置，該裝置包含一對電極；以及一有機發光單元，配置於該對電極之間，其中該有機發光單元包含上述之有機金屬化合物，可作為紅光磷光摻雜材料。
以下藉由數個實施例及比較實施例，以更進一步說明本發明之方法、特徵及優點，但並非用來限制本發明之範圍，本發明之範圍應以所附之申請專利範圍為準。
有機金屬化合物
本發明係揭露一種有機金屬化合物，係為具有式(I)所示之化學式：
其中，X係為C-H或是N，Y係為CH2 或是NH；R1 係氫、或C1-8 烷基；以及A1 係乙醯丙酮(acetylacetone)配位基、具有苯環之乙醯丙酮(acetylacetone)配位基、或其衍生物。
根據本發明之實施例，A1 之另一側係以氧原子與Ir鍵結，A1 之另一側同樣係以氧原子與Ir鍵結。
根據本發明其他實施例，該有機金屬化合物可具有如式(III)、式(IV)、或式(V)所示之結構：
其中，R1 係氫、或C1-8 烷基；R2 係為氫、苯基(phenyl)、苯基衍生物、或聯苯基(biphenyl)；Y係為CH2 或是NH。表1係列舉出本發明一系列較佳實施例所得之具有公式(I)或式(II)之有機金屬化合物，其各自之化學結構均詳列於表中，因此可清楚辨識其不同取代基所分別代表的官能基。
為進一步說明本發明有機金屬化合物的製備方法，以下特別詳述實施例1-4所示之化合物其製備流程。
實施例1化合物Ir-THQ-acac之合成
取化合物1(2.00 g,10.00 mmole)放入250 mL單頸瓶中，加入50.00 mL甲苯(toluene)並接上加料漏斗。接著在加料漏斗中加入市售化合物2(1.29 g,10.00 mmole)、碳酸鉀(2M,20 mL)、Pd(PPH3 )4 (0.43g)、及(t-Bu)3 P)(0.23g)，於室溫下加入反應瓶中，加熱迴流24小時。反應完成及純化後，可得化合物3(，69%)。上述反應之反應式如下所示：
將化合物3(1.00g,4.90mmole)放入250 mL單頸圓底瓶中，加入鐵粉(2.17 g,38.90 mmol)與EtOH:AcOH:H2 O=2:2:1的混合溶劑50 mL。使用機械攪拌，加熱迴流15分鐘，室溫下攪拌25分鐘，抽氣過濾將鐵粉等固體濾掉，以NaHCO3中和之，以乙酸乙酯和水萃取，減壓濃縮後，可得到淡褐色液體，不需經過管柱層析，就可以得到純度高化合物4，產率91%。上述反應之反應式如下所示：
將化合物4(1.00g,5.70 mmole)放入250 mL單頸圓底瓶中，加入甲苯(100 mL)，加熱至甲苯迴流。反應數小時後，加入1當量TFA及化合物5(0.97g)，並通入氧氣，持續加熱至甲苯迴流。反應完成後，可得化合物6(79%)。上述反應之反應式如下所示：
將化合物6(3.68g,11.60mmol)和水合氯化銥化合物(IrCl3 .xH2O,1.65g)放入100 mL單頸圓底瓶中，分別加入2-methoxy ethanol(15 mL)和水(5 mL)，加熱至140℃。反應24小時後，分別加入acac(、0.72g)、碳酸鈉(0.76g)和30 mL的2-methoxyethanol，加熱至140℃。反應24小時後，回至室溫，加入50 mL水，過濾，可得紅色固體產物。再以管柱層析法純化(二氯甲烷/正己烷=1/3)，得到Ir-THQ-acac。上述反應之反應式如下所示：
利用核磁共振光譜分析Ir-THQ-acac，所得之光譜資訊如下：1 H NMR(CDCl3 ,200 MHz) δ 8.49(d,J =5.4 Hz,2H),8.41(d,J =8.8 Hz,2H)，8.23(d,J =8.4 Hz,2H),8.02(d,J =7.6 Hz,2H),7.69(d,J =5.4 Hz,2H),7.44(t,J =8.0 Hz,2H),7.28(t,J =8.0 Hz,2H),7.03(dd,J =8.0,1.8 Hz,2H),6.71(d,J =1.8 Hz,2H),4.47(s,1H),1.35(s,6H),0.88(s,18H)。
實施例2化合物Ir-THQ-phac之合成
將化合物6(3.68g,11.60mmol)和水合氯化銥化合物(IrCl3 .xH2O,1.65 g)放入100 mL單頸圓底瓶中，分別加入2-methoxy ethanol(15 mL)和水(5 mL)，加熱至140℃。反應24小時後，分別加入化合物7(1.30g)、碳酸鈉(0.76 g)和30 mL的2-methoxyethanol，加熱至140℃。反應24小時後，回至室溫，加入50 mL水，過濾，可得紅色固體產物。再以管柱層析法純化(二氯甲烷/正己烷=1/3)，得到Ir-THQ-phac。上述反應之反應式如下所示：
利用核磁共振光譜分析Ir-THQ-phac，所得之光譜資訊如下：1 H NMR(CDCl3 ,200 MHz) δ 8.51(d,J =5.4 Hz,2H),8.45(d,J =8.8 Hz,2H),8.28(d,J =8.4 Hz,2H),8.08(d,J =7.6 Hz,2H),7.71(d,J =5.4 Hz,2H),7.66(d,J =8.0 Hz,2H),7.46(t,J =8.0 Hz,2H),7.41(d,J =1.8 Hz,1H),7.28(t,J =8.0 Hz,2H),7.13(dd,J =8.0,1.8 Hz,2H),7.03(dd,J =8.0,1.8 Hz,2H),6.73(d,J =1.8 Hz,2H),1.36(s,6H),0.89(s,18H)。
實 施例3化合物Ir-THQ-N-acac之合成
取化合物8(2.02g,10.00 mmole)放入250 mL單頸瓶中，加入50.00 mL甲苯(toluene)並接上加料漏斗。接著在加料漏斗中加入市售化合物9(1.29 g,10.00 mmole)、碳酸鉀(2M,20 mL)、Pd(PPH3 )4 (0.43g)、及(t-Bu)3 P)(0.23g)，於室溫下加入反應瓶中。反應完成及純化後，可得化合物10。上述反應之反應式如下所示：
將化合物10(1.01g,4.90mmole)放入250 mL單頸圓底瓶中，加入鐵粉(2.17 g,38.90 mmol)與EtOH:AcOH:H2 O=2:2:1的混合溶劑50 mL。使用機械攪拌，加熱迴流15分鐘，室溫下攪拌25分鐘，抽氣過濾將鐵粉等固體濾掉，以NaHCO3 中和之，以乙酸乙酯和水萃取，減壓濃縮後，可得到淡褐色液體，不需經過管柱層析，就可以得到純度高化合物11。上述反應之反應式如下所示：
將化合物11(1.00g,5.70 mmole)放入250 mL單頸圓底瓶中，加入甲苯(100 mL)，加熱至甲苯迴流。反應數小時後，加入1當量TFA及化合物5(0.97g)，並通入氧氣，持續加熱至甲苯迴流。反應完成後，可得化合物12(72%)。上述反應之反應式如下所示：
將化合物12(3.69g,11.60mmol)和水合氯化銥化合物(IrCl3 .xH2O,1.65g)放入100 mL單頸圓底瓶中，分別加入2-methoxy ethanol(15 mL)和水(5 mL)，加熱至140℃。反應24小時後，分別加入acac(、0.72g)、碳酸鈉(0.76 g)和30 mL的2-methoxyethanol，加熱至140℃。反應24小時後，回至室溫，加入50 mL水，過濾，可得紅色固體產物。再以管柱層析法純化(二氯甲烷/正己烷=1/3)，得到Ir-THQ-N-acac。上述反應之反應式如下所示：
實施例4化合物Ir-THQ-N-phac之合成
將化合物12(3.69g,11.60mmol)和水合氯化銥化合物(IrCl3 .xH2O,1.65 g)放入100 mL單頸圓底瓶中，分別加入2-methoxy ethanol(15 mL)和水(5 mL)，加熱至140℃。反應24小時後，分別加入化合物7(1.30g)、碳酸鈉(0.76 g)和30 mL的2-methoxyethanol，加熱至140℃。反應24小時後，回至室溫，加入50 mL水，過濾，可得紅色固體產物。再以管柱層析法純化(二氯甲烷/正己烷=1/3)，得到Ir-THQ-N-phac 。上述反應之反應式如下所示：
有機電激發光裝置
請參照第1圖，係顯示一符合本發明所述之有機電激發光裝置10之剖面結構示意圖，該有機電激發光裝置10包括一基底12、一下電極14、一有機發光單元16及一上電極18。該有機電激發光裝置10可為上發光、下發光、或雙面發光有機電激發光裝置。該基底可例如為玻璃、塑膠基板、或半導體基板。該下電極14及上電極18之材質可例如為鋰、鎂、鈣、鋁、銀、銦、金、鎢、鎳、鉑、銅、銦錫氧化物(ITO)、銦鋅氧化物(IZO)、鋅鋁氧化物(AZO)、氧化鋅(ZnO)或其結合，而其形成方式可為熱蒸鍍、濺射或電漿強化式化學氣相沉積方式。此外，該下電極14及上電極18至少一者需具有透光的性質。
該有機發光單元16至少包含一發光層，可更包含一電洞注入層、一電洞傳輸層、一電子傳輸層、一電子注入層或其他膜層。值得注意的是，根據本發明較佳實施例，該有機發光單元16必需包含本發明所述具有公式(I)或式(II)之有機金屬化合物。換言之，在該有機發光單元16中，至少有一膜層包含該有機金屬化合物。
根據本發明另一較佳實施例，該有機電激發光裝置可為一磷光有機電激發光裝置，而該磷光發光單元之發光單元包含一主體(host)材料及一磷光摻雜材料，而該磷光摻雜材料材料包含本發明所述具有式(I)或式(II)所示結構之有機金屬化合物。熟悉本技術者可視所使用之有機電激發光材料及所需之元件特性，將本發明所述之有機金屬化合物與所需的磷光摻雜材料摻雜，並改變所搭配的摻雜物之摻雜量。因此，摻雜物之摻雜量之多寡非關本發明之特徵，非為限制本發明範圍之依據。
為進一步說明本發明有機電激發光裝置，以下實施例係將由實施例1所得之有機金屬化合物作為摻雜材料，提供數個有機電激發光裝置的實施例，來驗證本發明所述之有機金屬化合物具有突出的光電特性。
實施例5:
使用中性清潔劑、丙酮、及乙醇以超音波振盪將已製作圖樣的ITO(厚度為100nm)玻璃基底洗淨。
接著，以氮氣將基材吹乾，然後UV-OZONE 30分鐘，接著於10-6 torr的壓力下依序沉積NPB(N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine、厚度為40nm)、CBP(4,4'-N,N'-dicarbazole-biphenyl)摻雜Ir-THQ-acac()(CBP與Ir-THQ-acac的比例為100:3、厚度為30nm)、Bphen(4,7-diphenyl-1,10-phenanthroline、厚度為30nm)、LiF(厚度為0.5nm)、及Al(厚度為120nm)，封裝後獲致該電激發光裝置(1)。該電激發光裝置(1)之結構可表示為：
NPB(40nm)/CBP: Ir-THQ-acac(3%)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)
接著，量測該電激發光裝置(1)之光學特性，其量測結果如下：最佳元件發光效率在34.1 cd/A，19.5 lm/W；元件效率在11.9 cd/A，4.2 lm/W＠1000 cd/m2 ；電激發光波長(EL)為612nm，CIE座標為(0.63,0.35)。
實施例6:
使用中性清潔劑、丙酮、及乙醇以超音波振盪將已製作圖樣的ITO(厚度為100nm)玻璃基底洗淨。
接著，以氮氣將基材吹乾，然後UV-OZONE 30分鐘，接著於10-6 torr的壓力下依序沉積NPB(N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine、厚度為40nm)、CBP(4,4'-N,N'-dicarbazole-biphenyl)摻雜Ir-THQ-acac()(CBP與Ir-THQ-acac的比例為100:4、厚度為30nm)、Bphen(4,7-diphenyl-1,10-phenanthroline、厚度為30nm)、LiF(厚度為0.5nm)、及Al(厚度為120nm)，封裝後獲致該電激發光裝置(2)。該電激發光裝置(2)之結構可表示為：NPB(40nm)/CBP: Ir-THQ-acac(4%)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)接著，量測該電激發光裝置(2)之光學特性，其量測結果如下：最佳元件發光效率在35.9 cd/A，28.2 lm/W；元件效率在11.4 cd/A，5.71m/W ＠1000 cd/m2；電激發光波長(EL)為616nm，CIE座標為(0.65,0.34)。
實施例7 :
使用中性清潔劑、丙酮、及乙醇以超音波振盪將已製作圖樣的ITO(厚度為100nm)玻璃基底洗淨。
接著，以氮氣將基材吹乾，然後UV-OZONE 30分鐘，接著於10-6 torr的壓力下依序沉積NPB(N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine、厚度為40nm)、CBP(4,4'-N,N'-dicarbazole-biphenyl)摻雜Ir-THQ-acac()(CBP與Ir-THQ-acac的比例為100:5、厚度為30nm)、Bphen(4,7-diphenyl-1,10-phenanthroline、厚度為30nm)、LiF(厚度為0.5nm)、及Al(厚度為120nm)，封裝後獲致該電激發光裝置(3)。該電激發光裝置(3)之結構可表示為：NPB(40nm)/CBP: Ir-THQ-acac(4%)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)接著，量測該電激發光裝置(3)之光學特性，其量測結果如下：最佳元件發光效率在18.7 cd/A，9.7 lm/W；元件效率在10.0 cd/A，3.5 lm/W ＠1000 cd/m2 ；電激發光波長(EL)為616nm，CIE座標為(0.65,0.34)。
雖然本發明已以較佳實施例揭露如上，然其並非用以限定本發明，任何熟習此技藝者，在不脫離本發明之精神和範圍內，當可作些許之更動與潤飾，因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。
10．．．有機電激發光裝置
12．．．基底
14．．．下電極
16．．．有機發光單元
以及
18．．．上電極
第1圖係為本發明一較佳實施例所述之有機電激發光裝置的剖面結構圖。
10．．．有機電激發光裝置
12．．．基底
14．．．下電極
16．．．有機發光單元
18．．．上電極

Claims (7)

  1. 一種有機金屬化合物，其係具有如式(I)所示之結構： 其中，X係為C-H或是N，Y係為CH2 或是NH；R1 係氫、或C1-8 烷基；以及A1 係乙醯丙酮(acetylacetone)配位基、具有苯環之乙醯丙酮(acetylacetone)配位基、或其衍生物。
  2. 如申請專利範圍第1項所述之有機金屬化合物，其中A1 之一側係以氧原子與Ir鍵結，A1 之另一側係以氧原子與Ir鍵結。
  3. 如申請專利範圍第1項所述之有機化合物，其中R1 係包含甲基、乙基、丙基、異丙基、丁基、異丁基、戊基、或己基。
  4. 如申請專利範圍第2項所述之有機金屬化合物，其係具有如式(III)、或式(IV)所示之結構： 其中，R1 係氫、或C1-8 烷基；R2 係為氫、苯基(phenyl)、苯基衍生物、或聯苯基(biphenyl)；Y係為CH2 或是NH。
  5. 如申請專利範圍第4項所述之有機金屬化合物， 其中該有機金屬化合物係為、、、或。
  6. 一種有機電激發光裝置，包括：一對電極；以及一有機發光單元，配置於該對電極之間，其中該有機發光單元包含具有式(I)所示結構之化合物： 其中，X係為C-H或是N，Y係為CH2 或是NH；R1 係氫、或C1-8 烷基；以及A1 係乙醯丙酮(acetylacetone)配位基、具有苯環之乙醯丙酮(acetylacetone)配位基、或其衍生物。
  7. 如申請專利範圍第6項所述之有機電激發光裝置，其中該發光單元係發出紅光。
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CN102911212A (zh) 2013-02-06
JP5544390B2 (ja) 2014-07-09
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