TW201927742A - 有機化合物及使用其的有機電激發光元件 - Google Patents

有機化合物及使用其的有機電激發光元件 Download PDF

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TW201927742A
TW201927742A TW107132838A TW107132838A TW201927742A TW 201927742 A TW201927742 A TW 201927742A TW 107132838 A TW107132838 A TW 107132838A TW 107132838 A TW107132838 A TW 107132838A TW 201927742 A TW201927742 A TW 201927742A
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organic compound
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顏豐文
鄧進銘
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機光科技股份有限公司
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Abstract

揭示了可在有機電激發光元件中用作發光層的磷光主體材料、螢光主體材料、或螢光摻雜材料、及/或電子傳輸材料的有機化合物。採用該有機化合物的有機電激發光元件可以降低驅動電壓、延長半衰期、及提高電流效率。

Description

有機化合物及使用其的有機電激發光元件
本發明係關於一種新穎的有機化合物，更具體言之係關於一種使用該有機化合物的有機電激發光元件。
有機電激發光（有機EL）元件是一種有機發光二極體（OLED），其中發光層是由有機化合物製成的膜，有機化合物可響應電流而發光。包含有機化合物的發光層被夾置於兩個電極之間。有機EL元件由於其高照度、重量輕、超薄外形、自照明而無需背光、低功耗、廣視角、高對比、製造方法簡單以及反應時間快速而被應用於平板顯示器。
典型上，有機EL元件係由位於兩個電極之間的有機材料層構成。有機材料層包括例如電洞注入層（HIL）、電洞傳輸層（HTL）、發光層（EML）、電子傳輸層（ETL）、及電子注入層（EIL）。有機電激發光的基本機制涉及載子（carrier）的注入、傳輸、及復合以及激子（exciton）的形成，以進行發光。當施加外部電壓到有機EL元件時，電子和電洞分別從陰極和陽極注入。電子從陰極注入LUMO（最低未佔用分子軌域）中，而電洞從陽極注入HOMO（最高佔用分子軌域）中。隨後，電子在發光層中與電洞重組而形成激子，然後激子失活而發光。當發光分子吸收能量而達到激發態時，依據電子和電洞的自旋組合，激子可呈單重態或三重態。眾所周知，在電激發下形成的激子通常包括25％的單重態激子和75％的三重態激子。然而，在螢光材料中，75％的三重態激子中的電生成能量將作為熱量消散，因為從三重態衰減是自旋禁阻（spin forbidden）的。因此，螢光電激發光元件僅具有25%的內部量子效率（internal quantum efficiency），導致理論上最高的外部量子效率（EQE）僅有5％，因為元件的光輸出耦合效率只有約20％。相較於螢光電激發光元件，磷光有機EL元件利用自旋─軌域相互作用（spin-orbit interacttion）來促進單重態與三重態之間的系統間穿越（intersystem crossing），因此來自單重態和三重態的發光皆可取得，而且電激發光元件的內部量子效率可自25％升至100％。
對於使用有機EL元件的全彩平板顯示器來說，有機EL元件中使用的有機材料在半衰期、功耗、亮度及效率方面仍然無法令人滿意。除了以上所述之外，AMOLED的深藍光發射（CIE y坐標小於0.15）也需要改進。
因此，本發明之一目的是提供一種新穎的有機化合物及使用該有機化合物的有機EL元件，該有機EL元件可以表現出更高的亮度和電流效率、更長的半衰期、及改進的深藍光發射。
本發明之另一目的是提供一種新穎的有機化合物及使用該有機化合物的有機EL元件，該有機EL元件能夠在降低的電壓下操作並且表現出更高的電流效率和更長的半衰期。
本發明之又一目的是提供一種新穎的有機化合物及使用該有機化合物的有機EL元件，該有機EL元件可以表現出更高的亮度和電流效率及更長的半衰期。
本發明之又一目的是提供一種有機化合物，該有機化合物可在有機EL元件中用作發光層的磷光主體材料、螢光主體材料、或螢光摻雜材料、及/或電子傳輸材料，以改善功耗、亮度、電流效率、元件光色、或壽命。
依據本發明，一種可用於有機EL元件的有機化合物被揭示出。該有機化合物係由下式（I）表示：式（I） 其中m為0至11的整數；n為0至3的整數；X為O、S、C(R3 )(R4 )、N(Ar3 )、或Si(R5 )(R6 )；Ar1 、Ar2 、及Ar3 各自獨立為氫原子、鹵素、具有5至50個環原子的經取代或未經取代芳胺基、具有5至50個環原子的經取代或未經取代雜芳胺基、具有5至50個環原子的經取代或未經取代芳基、或具有5至50個環原子的經取代或未經取代雜芳基；以及R1 至R6 係獨立選自由氫原子、鹵素、具有1至30個碳原子的經取代或未經取代烷基、具有6至30個碳原子的經取代或未經取代芳基、具有6至30個碳原子的經取代或未經取代芳烷基、及具有3至30個碳原子的經取代或未經取代雜芳基所組成之群組。
本發明進一步揭示一種有機電激發光元件。該有機電激發光元件包含由陰極和陽極組成的一電極對、及在該電極對之間的一發光層及一個或更多個有機薄膜層。該發光層和該有機薄膜層中之至少一者包含式（I）的有機化合物。
本發明探究有機化合物及使用該有機化合物的有機電激發光元件。下面將詳細說明生產、結構及組成部分，以使本發明可被充分理解。本發明的應用顯然不受限於所屬技術領域中具有通常知識者熟知的具體細節。另一方面，不對眾所周知的一般組成部分和程序作詳細描述，以避免對本發明造成不必要的限制。現在將在下面更詳細地描述本發明的一些較佳實施例。然而，應當理解的是，除了本文明確描述的實施例之外，本發明還可實施於各種其他實施例中，也就是說，本發明還可被廣泛應用於其他實施例，且本發明的範圍不會因此受到明確的限制，只受隨附申請專利範圍的內容限制。
在本發明的一個實施例中，揭露了可以在有機EL元件中用作發光層的磷光主體材料、螢光主體材料、或螢光摻雜材料、及/或電子傳輸材料的有機化合物。該有機化合物係由下式（I）表示：式（I） 其中m為0至11的整數；n為0至3的整數；X為O、S、C(R3 )(R4 )、N(Ar3 )、或Si(R5 )(R6 )；Ar1 、Ar2 、及Ar3 各自獨立為氫原子、鹵素、具有5至50個環原子的經取代或未經取代芳胺基、具有5至50個環原子的經取代或未經取代雜芳胺基、具有5至50個環原子的經取代或未經取代芳基、或具有5至50個環原子的經取代或未經取代雜芳基；以及R1 至R6 係獨立選自由氫原子、鹵素、具有1至30個碳原子的經取代或未經取代烷基、具有6至30個碳原子的經取代或未經取代芳基、具有6至30個碳原子的經取代或未經取代芳烷基、及具有3至30個碳原子的經取代或未經取代雜芳基所組成之群組。
在一些實施例中，Ar1 、Ar2 、及Ar3 係獨立選自由經取代或未經取代的苯基、經取代或未經取代的聯苯基、經取代或未經取代的芴基、經取代或未經取代的苯并芴基、經取代或未經取代的萘基、經取代或未經取代的蒽基、經取代或未經取代的菲基、經取代或未經取代的芘基、經取代或未經取代的屈基（chrysenyl group）、經取代或未經取代的三亞苯基（triphenylenyl group）、經取代或未經取代的芳胺基、經取代或未經取代的雜芳胺基、經取代或未經取代的苯并咪唑基、經取代或未經取代的咔唑基、經取代或未經取代的雙咔唑基、經取代或未經取代的二苯并呋喃基、經取代或未經取代的二苯并噻吩基、經取代或未經取代的二苯基氧化膦基（diphenylphosphine oxide group）、經取代或未經取代的三嗪基、經取代或未經取代的二嗪基、經取代或未經取代的吡啶基、經取代或未經取代的啡啉基、經取代或未經取代的二氫吖啶基、經取代或未經取代的吩噻嗪基、經取代或未經取代的吩噁嗪基、以及經取代或未經取代的二氫吩嗪基所組成之群組。
在一些實施例中，Ar1 、Ar2 、或Ar3 表示以下取代基中之一取代基： 。
較佳地，該有機化合物為以下化合物中之一者： 以及。
在本發明的另一個實施例中，揭示了一種有機電激發光元件。該有機電激發光元件包含由陰極和陽極組成的一電極對、及在該電極對之間的一發光層及一個或更多個有機薄膜層。該發光層和該有機薄膜層中之至少一者包含式（I）的有機化合物。
在一些實施例中，包含該式（I）之有機化合物的該發光層為一主體材料。該主體材料可以是磷光主體材料或螢光主體材料。在某些實施例中，包含該式（I）之有機化合物的該發光層被用作一螢光摻雜材料。
在一些實施例中，包含該式（I）之有機化合物的該有機薄膜層為一電子傳輸層。
在本發明的另一實施例中，該有機電激發光元件為一發光面板。在本發明的其他實施例中，該有機電激發光元件為一背光面板。
將藉由以下的例示性實施例來清楚闡明本發明的有機化合物之詳細製備，但本發明並不限於此等例示性實施例。實施例1至實施例10說明本發明的有機化合物之製備，而實施例11至實施例13說明有機EL元件的製造及測試報告。 實施例1
中間物A之合成
將3 g（8.4 mmol）10-溴苯并[g]屈（合成參考資料：US 20100327266）、2.5 g（10.1 mmol）4,4,4',4',5,5,5',5'-八甲基-2,2'-雙(1,3,2-二噁硼烷）、0.12 g（0.1 mmol）Pd(PPh3 )4 、1.0 g（12.6 mmol）乙酸鈉、及60 ml 1,4-二噁烷的混合物除氣並置於氮氣下，然後在100℃下加熱6小時。反應完成後，使混合物冷卻至室溫。隨後，用乙酸乙酯和水萃取有機層，然後用無水硫酸鎂乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到中間物A（2.8 g，85％）。
中間物B之合成
將2 g（5.0 mmol）中間物A、1.7 g（5.0 mmol）5-溴-2-碘苯甲酸甲酯、0.06 g（0.05 mmol）Pd(PPh3 )4 、10 ml 2M Na2 CO3 水溶液、10 ml EtOH、及30 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫。 隨後，用二氯甲烷和水萃取有機層，然後用無水MgSO4 乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到中間物B（1.7 g，68％）。
中間物C之合成
在氮氣下，在乾燥的THF中攪拌1.5 g（3.1 mmol）中間物B的同時，向其中緩慢滴加甲基溴化鎂（6當量）。將混合物在室溫下攪拌16小時。反應完成後，緩慢加入少量的蒸餾水，然後將混合物依序用乙酸乙酯萃取及用水洗滌。然後用無水MgSO4 乾燥有機層以除去溶劑，得到殘餘物。隨後，將過量的磷酸溶劑（約10 ml）加到殘餘物中，然後將其在室溫下攪拌超過16小時。之後，緩慢加入蒸餾水（約50 ml），然後攪拌1小時。將沉澱的固體過濾之後，用二氯甲烷溶劑萃取濾出的固體，然後用氫氧化鈉水溶液洗滌。隨後，取出二氯甲烷溶劑層，然後使用硫酸鎂除去水分。最後，除去殘餘溶劑，得到中間物C（0.5 g，34％）。MS（m/z，FAB+）：474.1。
中間物D之合成
將2 g（5.0 mmol）中間物A、1.4 g（5.0 mmol）2,5-二溴硝基苯、0.06 g（0.05 mmol）Pd(PPh3 )4 、10 ml 2M Na2 CO3 水溶液、10 ml EtOH、及30 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫。隨後，用二氯甲烷和水萃取有機層，然後用無水MgSO4 乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到中間物D（0.8 g，35％）。
中間物E之合成
將1 g（2.1 mmol）中間物D、5.5 g（21.0 mmol）三苯基膦、及30 ml oDCB的混合物置於氮氣下，然後在180℃下加熱8小時。反應完成後，使混合物冷卻至室溫。將混合物倒入水中，然後過濾，得到中間物E（0.5 g，50％）。
中間物F之合成
將2.0 g（4.5 mmol）中間物E、1.1 g（6.7 mmol）溴苯、0.05 g（0.2 mmol）Pd(OAc)2 、0.1 g（0.4 mmol）三叔丁基鏻四氟硼酸鹽、0.9 g（9.0 mmol）叔丁醇鈉、及50 ml甲苯的混合物除氣並置於氮氣下，然後在120℃下加熱16小時。 反應完成後，使混合物冷卻至室溫。隨後，用二氯甲烷和水萃取有機層，然後用無水MgSO4 乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到中間物F（1.3 g，55％）。MS（m/z，FAB+）：523.5。
中間物G之合成
將2 g（4.2 mmol）中間物C、1.4 g（5.5 mmol）4,4,4',4',5,5,5',5'-八甲基-2,2'-雙(1,3,2-二噁硼烷)、0.24 g（0.2 mmol）Pd(PPh3 )4 、0.8 g（8.4 mmol）乙酸鈉、及60 ml 1,4-二噁烷的混合物除氣並置於氮氣下，然後在100℃下加熱6小時。反應完成後，使混合物冷卻至室溫。隨後，用乙酸乙酯和水萃取有機層，然後用無水硫酸鎂乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到中間物G（1.7 g，80％）。
化合物C2之合成
將2.0 g（4.2 mmol）中間物C、1.2 g（5.5 mmol）雙(3,4-二甲基苯基)胺、0.05 g（0.2 mmol）Pd(OAc)2 、0.1 g（0.4 mmol）三叔丁基鏻四氟硼酸鹽、0.9 g（9.0 mmol）叔丁醇鈉、及60 ml鄰二甲苯的混合物除氣並置於氮氣下，然後在150℃下加熱8小時。反應完成後，使混合物冷卻至室溫。隨後，用二氯甲烷和水萃取有機層，然後用無水MgSO4 乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到化合物C2（1.9 g，75％）。MS（m/z，FAB+）：618.5。 實施例2
化合物C15之合成
將3 g（6.3 mmol）中間物C、2.1 g（9.4 mmol）蒽-9-基硼酸、0.07 g（0.06 mmol）Pd(PPh3 )4 、13 ml 2M Na2 CO3 水溶液、30 ml EtOH、及90 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫，然後過濾，得到化合物C15（3.1 g，88％）。MS（m / z，FAB+）：571.5。 實施例3
化合物C29之合成
將1 g（1.9 mmol）中間物G、1.1 g（4.4 mmol）2-氯-4,6-二苯基-1,3,5-三嗪、0.01 g（0.01 mmol）Pd(PPh3 )4 、4 ml 2M Na2 CO3 水溶液、10 ml EtOH、及30 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫。隨後，用二氯甲烷和水萃取有機層，然後用無水MgSO4 乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到化合物C29（0.6 g，53％）。MS（m/z，FAB+）：626.5。 實施例4
化合物C37之合成
將1 g（1.9 mmol）中間物G、1.0 g（4.4 mmol）2-氯-1,10-啡啉、0.01 g（0.01 mmol）Pd(PPh3 )4 、4 ml 2M Na2 CO3 水溶液、10 ml EtOH、及30 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫。隨後，用二氯甲烷和水萃取有機層，然後用無水MgSO4 乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到化合物C37（0.7 g，68％）。MS（m/z，FAB+）：573.6。 實施例5
化合物C23之合成
將1 g（1.9 mmol）中間物F、1.1 g（2.9 mmol）9-苯基-3-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-9H-咔唑、0.11 g（0.06 mmol）Pd(PPh3 )4 、3.8 ml 2M Na2 CO3 水溶液、20 ml EtOH、及60 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫，然後過濾，得到化合物C23（1.1 g，82％）。MS（m/z，FAB+）：685.8。 實施例6
中間物H之合成
將10 g（43.9 mmol）5-甲氧基聯苯-2-基硼酸、12.4 g（43.9 mmol）1,4-二溴萘、0.5 g（0.44 mmol）Pd(PPh3 )4 、87.8 ml 2M Na2 CO3 水溶液、100 ml EtOH、及300 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫，然後過濾，得到中間物H（12.6 g，74％）。
中間物I之合成
將10 g（25.7 mmol）中間物H、0.07 g（0.25 mmol）碘、及1000 ml苯的混合物除氣並置於氮氣下，然後在UV光下暴露4小時。反應完成後除去溶劑，然後將殘餘物再結晶3次，得到中間物I（2.3 g，23％）。
中間物J之合成
將2 g（5.2 mmol）中間物I、1.4 g（5.5 mmol）4,4,4',4',5,5,5',5'-八甲基-2,2'-雙(1,3,2-二噁硼烷)、0.30 g（0.2 mmol）Pd(PPh3 )4 、0.6 g（7.8 mmol）乙酸鈉、及50 ml 1,4-二噁烷的混合物除氣並置於氮氣下，然後在100℃下加熱6小時。反應完成後，使混合物冷卻至室溫。隨後，用乙酸乙酯和水萃取有機層，然後用無水硫酸鎂乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到中間物J（1.7 g，65％）。
中間物K之合成
將1 g（2.3 mmol）中間物J、0.6 g（2.3 mmol）2-碘苯甲酸甲酯、0.05 g（0.05 mmol）Pd(PPh3 )4 、1.2 ml 2M Na2 CO3 水溶液、10 ml EtOH、及30 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫，然後過濾，得到中間物K（1.0 g，80％）。
中間物L之合成
在氮氣下，在乾燥的THF中攪拌1.5 g（3.4 mmol）中間物K的同時，向其中緩慢滴加甲基溴化鎂（6當量）。將混合物在室溫下攪拌過夜。反應完成後，緩慢加入少量的蒸餾水，然後將混合物用乙酸乙酯萃取及用水洗滌。用無水MgSO4 乾燥有機層，然後移除溶劑以得到殘餘物。隨後，將過量的磷酸溶劑（約10 ml）加到殘餘物中，然後將其在室溫下攪拌超過16小時。之後，緩慢加入蒸餾水（約50 ml），然後攪拌1小時。將沉澱的固體過濾之後，用二氯甲烷溶劑萃取濾出的固體，然後用氫氧化鈉水溶液洗滌。隨後，取出二氯甲烷溶劑層，然後使用硫酸鎂除去水分。最後，除去殘餘溶劑，得到中間物L（0.4 g，30％）。
化合物C87之合成
將1.0 g（2.3 mmol）中間物L、1.2 g（5.2 mmol）雙(3,4-二甲基苯基)胺、0.21 g（0.23 mmol）Pd2 (dba)3 、0.5 g（4.6 mmol）叔丁醇鉀、及30 ml甲苯的混合物除氣並置於氮氣下，然後在110℃下加熱16小時。反應完成後，使混合物冷卻至室溫。隨後，用二氯甲烷和水萃取有機層，然後用無水MgSO4 乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到化合物C87（1.0 g，72％）。 MS（m/z，FAB+）：618.3。 實施例7
中間物M之合成
在氮氣下將1 g（1.9 mmol）中間物L和二氯甲烷（30 ml）的混合物放入反應器中。向其中加入三溴化硼（1當量），然後攪拌2小時，直到反應結束。用二氯甲烷和水萃取反應混合物，然後用無水MgSO4 乾燥。將溶劑移除得到中間物M（0.63 g，產率 = 88％）。
中間物N之合成
將1 g（2.4 mmol）中間物M、0.7 g（2.8 mmol）4,4,4',4',5,5,5',5'-八甲基-2,2'-雙(1,3,2-二噁硼烷）、0.12 g（0.1 mmol）Pd(PPh3 )4 、0.3 g（3.6 mmol）乙酸鈉、及30 ml 1,4-二噁烷的混合物除氣並置於氮氣下，然後在100℃下加熱6小時。反應完成後，使混合物冷卻至室溫。隨後，用乙酸乙酯和水萃取有機層，然後用無水硫酸鎂乾燥。將溶劑移除之後，藉由矽膠管柱層析純化殘餘物，得到中間物N（1.0 g，65％）。
化合物C88之合成
將1 g（1.9 mmol）中間物N、0.6 g（1.2 mmol）1-溴芘、0.11 g（0.09 mmol）Pd(PPh3 )4 、1.0 ml 2M Na2 CO3 水溶液、10 ml EtOH、及30 ml甲苯的混合物除氣並置於氮氣下，然後在100℃下加熱12小時。反應完成後，使混合物冷卻至室溫，然後過濾得到化合物C88（1.0 g，88％）。MS（m/z，FAB+）：595.2。 實施例8
中間物O之合成
使用與中間物H之合成中相同的合成程序，不同之處僅在於使用10 g的5-溴苯并[d]萘并[2,1-b]呋喃取代1,4-二溴萘，得到期望的中間物O（11.6 g，66％）。
中間物P之合成
使用與中間物I之合成中相同的合成程序，不同之處僅在於使用11.6 g的中間物O取代中間物H，得到期望的中間物P（3.2 g，28％）。
中間物Q之合成
使用與中間物M之合成中相同的合成程序，不同之處僅在於使用10 g的中間物P取代中間物L，得到期望的中間物Q（8.5 g，88％）。
中間物R之合成
使用與中間物N之合成中相同的合成程序，不同之處僅在於使用8.5 g的中間物Q取代中間物M，得到期望的中間物R（7.3 g，65％）。
化合物C89之合成
使用與化合物C88之合成中相同的合成程序，不同之處僅在於使用2 g的中間物R取代中間物N，並使用2-氯-4,6-二苯基-1,3,5-三嗪取代1-溴芘，得到期望的化合物C89（0.7 g，60％）。 實施例9
中間物S之合成
使用與中間物H之合成中相同的合成程序，不同之處僅在於使用10 g的5-溴苯并[d]萘并[2,1-b]噻吩取代1,4-二溴萘，得到期望的中間物S（10.0 g，55％）。
中間物T之合成
使用與中間物I之合成中相同的合成程序，不同之處僅在於使用10.0 g的中間物S取代中間物H，得到期望的中間物T（3.2 g，32％）。
中間物U之合成
使用與中間物M之合成中相同的合成程序，不同之處僅在於使用3.2 g的中間物T取代中間物L，得到期望的中間物U（2.5 g，80％）。
中間物V之合成
使用與中間物N之合成中相同的合成程序，不同之處僅在於使用3.2 g的中間物U取代中間物M，得到期望的中間物V（2.9 g，75％）。
化合物C90之合成
使用與化合物C88之合成中相同的合成程序，不同之處僅在於使用2 g的中間物V取代中間物N，並使用1.3 g的10-(4-溴苯基)-10H-吩噁嗪取代1-溴芘，得到期望的化合物C90（1.9 g，76％）。 實施例10
中間物W之合成
使用與中間物H之合成中相同的合成程序，不同之處僅在於使用10 g的5-氯-7,7-二甲基-7H-苯并[d]萘并[2,1-b]噻咯取代1,4-二溴萘，得到期望的中間物W（12.0 g，62％）。
中間物X之合成
使用與中間物I之合成中相同的合成程序，不同之處僅在於使用12.0 g的中間物W取代中間物H，得到期望的中間物X（2.5 g，21％）。
中間物Y之合成
使用與中間物M之合成中相同的合成程序，不同之處僅在於使用2.5 g的中間物X取代中間物L，得到期望的中間物Y（1.5 g，64％）。
中間物Z之合成
使用與中間物N之合成中相同的合成程序，不同之處僅在於使用1.5 g的中間物Y取代中間物M，得到期望的中間物Z（1.3 g，69％）。
化合物C91之合成
使用與化合物C88之合成中相同的合成程序，不同之處僅在於使用1.3 g的中間物Z取代中間物N，並使用0.7 g的3-溴-9-苯基-9H-咔唑取代1-溴芘，得到期望的化合物C91（1.3 g，產率 = 85％）。 生產有機電激發光元件之一般方法
提供阻值為12歐姆/平方（ohm/square）及厚度為120 nm的銦錫氧化物塗層玻璃（以下稱為ITO基板），並在超音波浴（例如洗滌劑、去離子水）中進行多步驟清洗。在氣相沉積有機層之前，藉由紫外光（UV）和臭氧進一步處理清洗過的ITO基板。ITO基板的所有預處理製程皆在潔淨室（100級）內進行。
在高真空設備下（10-7 Torr）利用電阻加熱的石英舟以氣相沉積將這些有機層依序塗佈到ITO基板上。藉助石英晶體監視器來精確監控或設定各層的厚度和氣相沉積速率（0.1~0.3 nm/sec）。如上所述，還可以使個別層包含不只一種化合物，即通常摻雜有摻雜材料的主體材料。此可藉由來自兩個或更多個來源的共氣相沉積成功地實現，表示本發明的有機化合物是熱穩定的。
使用二吡嗪并[2,3-f:2',3'-h]喹喔啉-2,3,6,7,10,11-六腈（dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile）（HAT-CN）形成電洞注入層，並使用N,N-雙(萘-1-基)-N,N-雙(苯基)-聯苯胺（NPB）形成有機EL元件的電洞傳輸層。使用2,9-雙(萘-2-基)-4,7-二苯基-1,10-啡啉（NPhen）作為有機EL元件的電子傳輸材料，因其相較於BPhen或BCP具有更高的熱穩定性和更長的壽命。對於螢光發光元件，使用1,1'-(9,9-二甲基-9H-芴-2,7-二基)二芘（DFDP）作為主體材料，並使用(E)-6-(4-(二苯基胺基)苯乙烯基)-N,N-二苯基萘-2-胺（D1）作為螢光摻雜劑。對於磷光發光元件，使用雙(2-甲基-8-羥基喹啉)-4-(苯基苯酚)鋁（BAlq）作為發光層的主體材料，並使用三(1-苯基異喹啉) 銥（III）（Ir(piq)3 ）或三(2-苯基喹啉)銥（III）（Ir(2-phq)3 ）作為摻雜材料。使用化合物C15、C17、C53、C86、及C88作為螢光主體材料來與DFDP比較。使用中間物C、C2、C5、C6、C7、C56、C79、C87、及C90作為螢光摻雜材料來與D1比較。使用化合物C29、C37、C42、C70、及C89作為電子傳輸材料來與NPhen比較。使用化合物C23、C29及C91作為磷光主體材料來與BAlq比較。本發明中用於製作對照和例示性有機EL元件的傳統OLED材料和本發明的例示性有機化合物之化學結構如下所示： 中間物CC2C5C6C7C15C17C23C29C37C42C53C56C70C79C86C87C88C89C90C91。
有機EL元件一般包含透過熱蒸發形成為陰極的低功函數金屬，例如Al、Mg、Ca、Li及K，且該低功函數金屬可有助於電子從陰極注入電子傳輸層。另外，在陰極與電子傳輸層之間引入薄膜電子注入層，用於降低電子注入阻障並改善有機EL元件的性能。習知的電子注入層材料為具有低功函數的金屬鹵化物或金屬氧化物，例如：LiF、MgO、或Li2 O。
另一方面，在製作有機EL元件之後，透過使用PR650光譜掃描光譜儀量測EL光譜及CIE座標。此外，使用吉時利（Keithley）2400可程式化電壓電流源測得電流/電壓、亮度/電壓、及效率/電壓特性。在室溫（約25℃）及大氣壓下操作上述設備。 實施例11
使用與上述一般方法類似的程序製作發射藍色螢光並具有以下如圖1所示元件結構的有機EL元件：ITO/HAT-CN（20 nm）/NPB（50 nm）/藍色螢光主體（DFDP、C15、C17、C53、C86、或C88）+ 5%摻雜劑（D1、中間物C、C2、C5、C6、C7、C56、C79、C87、或C90）（30 nm）/NPhen（30 nm）/LiF（0.5 nm）/Al（160 nm）。將此等發射藍色螢光的有機EL元件的I-V-B和半衰期測試報告總結於下表1，並將半衰期定義為3000 cd/m2 的初始亮度降低一半的時間。 表1
根據上述有機EL元件的測試報告總結，顯而易見的是，用作藍色螢光主體或摻雜材料的式（I）有機化合物表現出比現有技術的材料更佳的性能。具體來說，本發明使用式（I）的有機化合物作為摻雜材料或主體材料來與主體材料DFDP或摻雜材料D1搭配的有機EL元件在相同電壓下具有更高的亮度和電流效率、更長的半衰期、以及改進的深藍光發射。 實施例12
使用與上述一般方法類似的程序製作具有以下如圖1所示元件結構的有機EL元件：ITO/HAT-CN（20 nm）/NPB（50 nm）/ DFDP + 5% D1（30 nm）/NPhen或C29、C37、C42、C70、或C89（30 nm）/LiF（0.5 nm）/Al（160 nm）。將此等發射藍色螢光的有機EL元件的I-V-B和半衰期測試報告總結於下表2，並將半衰期定義為3000 cd/m2 的初始亮度降低一半的時間。 表2
根據上述有機EL元件的測試報告總結，顯而易見的是，用作電子傳輸材料的式（I）有機化合物表現出比現有技術的材料NPhen更佳的性能。具體來說，本發明的有機EL元件使用式（I）的有機化合物作為電子傳輸材料來與主體材料DFDP和摻雜材料D1搭配可具有更低的功耗、更高的電流效率、及更長的半衰期。 實施例13
使用與上述一般方法類似的程序製作發射磷光並具有以下如圖1所示元件結構的有機EL元件：ITO/HAT-CN（20 nm）/NPB（50 nm）/磷光主體（C29、C23、或C91）+ 10%摻雜劑（30 nm）/NPhen（30 nm）/LiF（0.5 nm）/Al（160 nm）。將此等發射磷光的有機EL元件的I-V-B和半衰期測試報告總結於下表3，並將半衰期定義為3000 cd/m2 的初始亮度降低一半的時間。 表3
根據上述有機EL元件的測試報告總結，顯而易見的是，用作磷光主體材料的式（I）有機化合物表現出比現有技術的材料BAlq更佳的性能。具體來說，本發明的有機EL元件使用式（I）的有機化合物作為磷光主體材料來與摻雜材料Ir(piq)3 或Ir(2-phq)3 搭配在相同電壓下可具有更高的亮度和電流效率及更長的半衰期。
總而言之，本發明揭示了有機化合物，該有機化合物可在有機EL元件中用作發光層的磷光主體材料、螢光主體材料、或螢光摻雜材料、或電子傳輸材料。所述的有機化合物係由下式（I）表示：式（I） 其中m為0至11的整數；n為0至3的整數；X為O、S、C(R3 )(R4 )、N(Ar3 )、或Si(R5 )(R6 )；Ar1 、Ar2 、及Ar3 各自獨立為氫原子、鹵素、具有5至50個環原子的經取代或未經取代芳胺基、具有5至50個環原子的經取代或未經取代雜芳胺基、具有5至50個環原子的經取代或未經取代芳基、或具有5至50個環原子的經取代或未經取代雜芳基；以及R1 至R6 係獨立選自由氫原子、鹵素、具有1至30個碳原子的經取代或未經取代烷基、具有6至30個碳原子的經取代或未經取代芳基、具有6至30個碳原子的經取代或未經取代芳烷基、及具有3至30個碳原子的經取代或未經取代雜芳基所組成之群組。
根據上述教示顯然可以作出許多的修改及變化。因此，應當瞭解的是，在隨附申請專利範圍的範圍內，可以以本文具體描述的方式以外的其他方式來實施本發明。雖然，本文中已說明並描述了具體實施例，但對於所屬技術領域中具有通常知識者來說，顯而易見的是可以在不偏離欲單獨由隨附申請專利範圍限制的情況下對本發明作出許多修改。
6‧‧‧透明電極
7‧‧‧電洞注入層
8‧‧‧電洞傳輸層
9‧‧‧發光層
10‧‧‧電子傳輸層
11‧‧‧電子注入層
12‧‧‧金屬電極
圖1顯示本發明的有機EL元件的一個實施例。在該元件中，電洞注入層7沉積在透明電極6上，電洞傳輸層8沉積在電洞注入層7上，螢光或磷光發光層9沉積在電洞傳輸層8上，電子傳輸層10沉積在發光層9上，電子注入層11沉積在電子傳輸層10上，以及金屬電極12沉積在電子注入層11上。

Claims (10)

  1. 一種以下式（I）之有機化合物：式（I）， 其中m為0至11的整數；n為0至3的整數；X為O、S、C(R3 )(R4 )、N(Ar3 )、或Si(R5 )(R6 )；Ar1 、Ar2 、及Ar3 各自獨立為氫原子、鹵素、具有5至50個環原子的經取代或未經取代芳胺基、具有5至50個環原子的經取代或未經取代雜芳胺基、具有5至50個環原子的經取代或未經取代芳基、或具有5至50個環原子的經取代或未經取代雜芳基；以及R1 至R6 係獨立選自由氫原子、鹵素、具有1至30個碳原子的經取代或未經取代烷基、具有6至30個碳原子的經取代或未經取代芳基、具有6至30個碳原子的經取代或未經取代芳烷基、及具有3至30個碳原子的經取代或未經取代雜芳基所組成之群組。
  2. 如請求項1所述之有機化合物，其中Ar1 、Ar2 、及Ar3 係獨立選自由經取代或未經取代的苯基、經取代或未經取代的聯苯基、經取代或未經取代的芴基、經取代或未經取代的苯并芴基、經取代或未經取代的萘基、經取代或未經取代的蒽基、經取代或未經取代的菲基、經取代或未經取代的芘基、經取代或未經取代的屈基（chrysenyl group）、經取代或未經取代的三亞苯基（triphenylenyl group）、經取代或未經取代的芳胺基、經取代或未經取代的雜芳胺基、經取代或未經取代的苯并咪唑基、經取代或未經取代的咔唑基、經取代或未經取代的雙咔唑基、經取代或未經取代的二苯并呋喃基、經取代或未經取代的二苯并噻吩基、經取代或未經取代的二苯基氧化膦基（diphenylphosphine oxide group）、經取代或未經取代的三嗪基、經取代或未經取代的二嗪基、經取代或未經取代的吡啶基、經取代或未經取代的啡啉基、經取代或未經取代的二氫吖啶基、經取代或未經取代的吩噻嗪基、經取代或未經取代的吩噁嗪基、以及經取代或未經取代的二氫吩嗪基所組成之群組。
  3. 如請求項1所述之有機化合物，其中Ar1 、Ar2 、或Ar3 表示以下取代基中之一取代基： 。
  4. 如請求項1所述之有機化合物，其中該有機化合物為以下化合物中之一化合物： 以及。
  5. 一種有機電激發光元件，包含由陰極和陽極組成的一電極對、及在該電極對之間的一發光層及一個或更多個有機薄膜層，其中該發光層和該有機薄膜層中之至少一者包含如請求項1所述之有機化合物。
  6. 如請求項5所述之有機電激發光元件，其中包含式（I）之該有機化合物的該發光層為一主體材料。
  7. 如請求項5所述之有機電激發光元件，其中包含式（I）之該有機化合物的該發光層為一螢光摻雜材料。
  8. 如請求項5所述之有機電激發光元件，其中包含式（I）之該有機化合物的該有機薄膜層為一電子傳輸層。
  9. 如請求項5所述之有機電激發光元件，其中該有機電激發光元件為一發光面板。
  10. 如請求項5所述之有機電激發光元件，其中該有機電激發光元件為一背光面板。
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