TWI703204B - 雜芳族化合物及使用其的有機電激發光組件 - Google Patents

雜芳族化合物及使用其的有機電激發光組件 Download PDF

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TWI703204B
TWI703204B TW108115754A TW108115754A TWI703204B TW I703204 B TWI703204 B TW I703204B TW 108115754 A TW108115754 A TW 108115754A TW 108115754 A TW108115754 A TW 108115754A TW I703204 B TWI703204 B TW I703204B
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carbon atoms
substituted
heteroaromatic compound
organic
group
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TW201947013A (zh
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顏豐文
莊立杰
黃尊遠
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機光科技股份有限公司
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Abstract

本發明提供了一種雜芳族化合物，其可用作有機電激發光組件發光層的螢光摻雜材料。比起既有的有機電激發光組件，使用該雜芳族化合物的有機電激發光組件，可具有更低的功耗、更高的發光電流效率、或更長的半衰期。

Description

雜芳族化合物及使用其的有機電激發光組件
本發明是關於一種雜芳族化合物，特別是關於一種使用該雜芳族化合物的有機電激發光(下文稱為有機EL)組件。
有機電激發光(有機EL)組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，有機化合物可回應電流而發光。包含有機化合物的發光層被夾置於兩個電極之間。有機EL組件由於其高照度、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組件是由位於兩個電極之間的有機材料層構成。有機材料層包括電洞傳輸層(hole transporting layer；HTL)、發光層(emitting layer；EML)、及電子傳輸層(electron transporting layer；ETL)。有機電激發光的基本原理涉及載子(carrier)的注入、傳輸、及複合以及激子(exciton)的形成，以進行發光。當向有機EL組件施加外部電壓時，電子和電洞分別從陰極和陽極注入。電子從陰極注入最低未佔用分子軌域(lowest unoccupied molecular orbital，LUMO) 中，而電洞從陽極注入最高佔用分子軌域(highest occupied molecular orbital，HOMO)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，螢光電激發光組件僅具有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％，因為組件的光輸出耦合效率只有約20％。相較於螢光電激發光組件，磷光有機EL組件利用自旋─軌域相互作用(spin-orbit interaction)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，而且電激發光組件的內部量子效率可自25％升至100％。
對於使用有機EL組件的平板顯示器來說，有機EL組件中使用的有機材料仍無法令人滿意。如果可以在延長半衰期、降低驅動電壓、或提高電流效率等等任何一方面，能有改善，都足以使有機EL組件或平板顯示器等相關產業有明顯的發展與提升。因此，本發明的目的之一，是提供一種有機化合物，可以降低有機EL組件的驅動電壓、或提高其電流效率、或延長其半衰期。
因此，本發明的目的是提供一種新的雜芳族化合物，可以作為有機EL組件發光層的螢光客體材料，能夠降低有機EL組件的驅動電壓、或提高其電流效率、或延長其半衰期，或改善功耗。
本發明的另一目的是提供一種雜芳族化合物，或使用該雜芳族化合物的有機電激發光組件，其可以較低的驅動電壓運作，或者操作出較高的電流效率，或較長的半衰期。
依據本發明，揭示了一種雜芳族化合物，可用作有機EL組件發光層的螢光摻雜材料。該雜芳族化合物可由下式(1)表示：
Figure AA1
 其中Ar1 及Ar2 獨立為具有4、5或6 (4至6)個環碳原子的芳基或雜芳基；Ar3 為具有5至6個環碳原子的環烷基、環烯基、或芳基；R1 及R2 獨立為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基；W表示二價橋並選自於由O、S、Se、CR8 R9 、NR10 和 SiR11 R12 組成的群組；X是不存在，或是二價橋並選自於由O、S、Se、CR8 R9 、NR10 和 SiR11 R12 組成的群組；A是不存在，或表示以下式(2)：
Figure 02_image003
式(2)， 其中Y可以表示二價橋並選自於由O、S、Se、CR13 R14 、NR15 和SiR16 R17 所組成的群組；R8 至R17 獨立為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基、或具有3至36個碳原子的經取代或未經取代雜芳基。
本發明進一步提供了一種有機電激發光組件。該有機電激發光組件包含由陰極和陽極組成的電極對、及在該電極對之間的發光層及一個或多個有機薄膜層，其中該發光層和該有機薄膜層中的至少一個包含式(1)所述的雜芳族化合物。
本發明欲探究前述有機材料以及使用此類有機材料的有機EL裝置。在下文中將提供生產、結構以及要素的詳細描述以使本發明可充分地被理解。顯然本發明的應用並不限於本領域所屬技術領域技術人員所熟悉的特定細節。另一方面，普遍周知的常見元素和過程並未詳細描述于本發明中，且不應對本發明產生不必要的限制。現將在下文中更詳細地描述本發明的一些較佳實施方式。但是，應認知的是，本發明可以在除明確描述的實施方式之外的廣泛多種其它實施方式中實踐，即，本發明還可以廣泛應用於其它實施方式，並且除了如本發明中所指定外，本發明的範圍不受明確限制。
在本發明實施方式中，涉及一種雜芳族化合物，可用作有機EL組件發光層的螢光摻雜材料。該雜芳族化合物可由下式(1)表示：
Figure AA1
 其中Ar1 及Ar2 獨立為具有4、5或6 (4至6)個環碳原子的芳基(優選苯基)、或具有4、5或6 (4至6)個環碳原子的雜芳基(優選4或5 個環碳原子的雜芳基；其中又更優選含S或N的雜芳基，最優選含S雜芳基)。 Ar3 為具有5至6個環碳原子的環烷基(優選；其中更優選5個環碳原子的環烷基、最優選具有5個環碳原子的環戊基)、具有5至6個環碳原子的環烯基(其中優選5個環碳原子的環戊烯基)、或具有5至6個環碳原子的芳基。 R1 為氫原子、具有1至36個碳原子的經取代或未經取代烷基(優選；更優選；最優選異丁基)、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基。 R2 為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基。 W表示二價橋並選自於由O、S、Se、CR3 R4 、NR5 和 SiR6 R7 組成的群組。其中，W優選O、S或CR8 R9 ，更優選O或S。R3 至R7 獨立為氫原子、或具有1至20個碳原子的經取代或未經取代烷基；其中，NR5 優選NCH3 ；CR3 R4 優選C(CH3 )2 或CH2 ；SiR6 R7 優選Si(CH3 )2 。 X是不存在，或是二價橋並選自於由O、S、Se、CR8 R9 、NR10 和 SiR11 R12 組成的群組(優選CR8 R9 )。可以理解的是，本發明所述的“X是不存在”，是指式（1）結構的右上方為開環，如下式（1’）所示：
Figure AA1
 A是不存在，或表示以下式(2)：
Figure 02_image003
式(2)， 其中Y可以表示二價橋並選自於由O、S、Se、CR13 R14 、NR15 和SiR16 R17 所組成的群組(優選S、CR13 R14 或NR15 ；更優選CR13 R14 或NR15 ；最優選CR13 R14 )，此時R2 可優選為氫原子。 R8 、R9 、R13 、及R14 獨立為氫原子、具有1至36個碳原子的經取代或未經取代烷基(優選具有1至20個碳原子的經取代或未經取代烷基；更優選具有1、2、或3個碳原子的經取代或未經取代烷基；最優選甲基)、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基、或具有3至36個碳原子的經取代或未經取代雜芳基。其中，CR8 R9 可以是C(CH3 )2 、CH2 、或表示以：
Figure 02_image007
。 且其中，CR13 R14 可以是C(CH3 )2 、或表示以：
Figure 02_image009
。 R10 至R12 、及 R16 至R17 獨立為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基、或具有3至36個碳原子的經取代或未經取代雜芳基。 其中，SiR11 R12 可以是Si(CH3 )2 ，或表示以：
Figure 02_image011
。 且其中，SiR16 R17 可以是Si(CH3 )2 、SH2 ，或表示以：
Figure 02_image013
。 且其中，NR10 可表示以：
Figure 02_image015
。 R15 為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基(優選具有6至20個碳原子的經取代或未經取代烷基；更優選具有6個碳原子的經取代或未經取代烷基；最優選苯基)、具有6至36個碳原子的經取代或未經取代芳烷基、或具有3至36個碳原子的經取代或未經取代雜芳基。其中，NR15 可表示以：
Figure 02_image017
。
在一些實施例中，Ar1 及Ar2 獨立為
Figure 02_image019
，
Figure 02_image021
，或
Figure 02_image023
。
在一些實施例中，Ar3 為
Figure 02_image025
或
Figure 02_image027
。
在一些實施方式，該雜芳族化合物可以由以下式(3)至式(12)中的一個表示：
Figure AA2
Figure AA3-1
Figure AA3
Figure AA4-1
Figure AA4
 。 優選地，該雜芳族化合物為以下化合物中之一化合物：
Figure 02_image050
Figure 02_image052
Figure 02_image054
Figure 02_image056
Figure 02_image058
Figure 02_image060
Figure 02_image062
Figure 02_image064
Figure 02_image066
Figure 02_image068
Figure 02_image070
Figure 02_image072
Figure 02_image074
Figure 02_image076
Figure 02_image078
Figure 02_image080
Figure 02_image082
Figure 02_image084
Figure 02_image086
Figure 02_image088
Figure 02_image090
Figure 02_image092
Figure 02_image094
Figure 02_image096
Figure 02_image098
Figure 02_image100
Figure 02_image102
Figure 02_image104
Figure 02_image106
Figure 02_image108
Figure 02_image110
Figure 02_image112
Figure 02_image114
Figure 02_image116
Figure 02_image118
Figure 02_image120
Figure 02_image122
Figure 02_image124
Figure 02_image126
Figure 02_image128
Figure 02_image130
Figure 02_image132
Figure 02_image134
Figure 02_image136
Figure 02_image138
Figure 02_image140
Figure 02_image142
Figure 02_image144
Figure 02_image146
Figure 02_image148
Figure 02_image150
Figure 02_image152
Figure 02_image154
Figure 02_image156
Figure 02_image158
。
本發明另一個實施方式，揭示了一種有機電激發光組件。該有機電激發光組件包含由陰極和陽極組成的電極對、及在該電極對之間的發光層及一個或多個有機薄膜層，其中該發光層和該有機薄膜層中的至少一個包含式(1)所述的雜芳族化合物。
在一些實施方式中，發光層所包含的式(1)雜芳族化合物可以是螢光摻雜材料。特別的，這樣的發光層可以發出藍色的螢光。
在本發明的另一實施方式中，該有機電激發光組件為一發光面板。在本發明的其他實施方式中，該有機電激發光組件為背光面板。
以下將通過實施例來清楚闡明本發明的雜芳族化合物的細節製備。可以理解的是，根據式(1)的主結構，先合成出類似主結構的目標化合物(例如，但不限於溴化物)，作為第一反應物，再根據式(1)的Ar1 、Ar2 及其兩者間的環戊烯A所組成的副結構，找出適當對應的酮類，作為第二反應物，就可以合成本發明各實施方式所要的各種化合物(包括但不限於式(1)、式(3)~式(12)表示的化合物，以及EX1~EX165)。然而，本發明並不限於這些實施例。實施例1至實施例7只是舉例說明本發明的雜芳族化合物的製備，而實施例8也僅只是舉例說明若干有機EL組件的製造及測試報告而已，並非用以限制本發明。 實施例1
中間體A的合成
Figure 02_image160
將13 g(40 mmol)的4,6-二溴苯並呋喃、11.3 g(40 mmol)的雙(4-叔丁基苯基)胺、0.9 g(0.8 mmol)的三(二亞苄基丙酮)二鈀(Pd2 (dba)3 )、1.2 g(0.6 mmol) 的三叔丁基磷(P(t-Bu)3 )、5.0 g(52 mmol)的叔丁醇鈉(NaOt Bu)、及150 ml甲苯的混合物置於氮氣下，然後在70o C下加熱24小時。反應完成後，使混合物冷卻至室溫。用100 ml的乙酸乙酯和300 ml水萃取有機層，然後用無水硫酸鎂乾燥。隨後，減壓除去溶劑，然後通過矽膠柱層析純化殘餘物，得到產物(16 g，30.4 mmol，76%)。
中間體B的合成
Figure 02_image162
將中間體A與100 ml的四氫呋喃(THF)混合物置於置於氮氣下，然後在-78o C下攪拌。逐滴加入2.5M正丁基鋰(n-BuLi)的正己烷溶液(13.6 mL)，使溫度上升至0o C。將溶液攪拌30分鐘，然後，溫度下降至-75o C，此時緩滴加入3.8 g (37 mmol)的甲基硼酸酯(Trimethylborate)。隨後，將混合物攪拌3小時，使溫度慢慢升至室溫。將3N的鹽酸加入混合物使其酸化後，以乙酸乙酯和水萃取有機層，然後用無水硫酸鎂乾燥。將殘餘物從甲苯再結晶，得到產物(11.2 g，22.8 mmol，75%)。
5,6-二溴-1,2-二氫苊的合成
Figure 02_image164
將100 g (650 mmol)的苊(Acenaphthene)以及150 ml二甲基甲醯胺(DMF)的混合物置於氮氣下，並在0o C下攪拌。在逐滴加入250 g (1430 mmol)的N-溴代丁二醯亞胺(N-bromosuccinimide，NBS)的500ml二甲基甲醯胺(DMF)溶液之後，溫度回升至室溫，並攪拌該混合物18小時。將沉澱的產物，抽氣過濾，並用乙醇洗滌，將殘餘物從乙醇再結晶，得到產物(46.5 g，149.5 mmol，23%)。
5-(10-溴蒽-9-基)- 7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b]吖啶的合成
Figure 02_image166
將2.9g(8.9mmol)的7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b]吖啶(7,7,13,13-tetramethyl-7,13- dihydro-5H-indeno-[1,2-b]acridine)、3g(8.9mmol)的9,10-二溴蒽、0.08g (0.36mmol)的乙酸鈀(Pd(OAc)2 )、2.56g (26.7mmol)的叔丁醇鈉(NaOtBu；sodium tert-butoxide)、及50ml的鄰二甲苯(o-Xylene)，五者的混合物脫氣並置於氮氣下，然後在140℃加熱12小時。反應完成後，使混合物冷卻至室溫。隨後，將150 ml的甲醇加到混合物中，得到的沉澱物經過濾並用甲醇洗滌，得到黃色固體。產率：21.23g，23%。1 H NMR (CDCl3 , 400 MHz)：化學位移(ppm) 8.11 (d, 2H), 7.91(d, 2H),7.83(d, H), 7.54 (d, 2H), 7.45-7.41(m, 5H), 7.35(m, H), 7.25 (m, H), 7.05-7.02(m, 2H), 6.79(m, H),6.69(d, H) ,6.58(d, H), 1.56(s, 6H), 1.39(s, 6H)。
中間體C的合成
Figure 02_image168
將3.1 g(10 mmol)的5,6-二溴-1,2-二氫苊、4.9 g(10 mmol)的中間體B、0.58 g(0.5 mmol)的四(三苯基磷)鈀(Pd(PPh3 )4 )、7 ml 2M的碳酸鉀(K2 CO3 )、40 ml的乙醇(EtOH)、及40 ml甲苯的混合物脫氣並置於氮氣下，然後在90℃下加熱過夜。反應完成後，使混合物冷卻至室溫。用乙酸乙酯和水分離並洗滌出有機層。用無水硫酸鎂乾燥後，在真空中除去溶劑。然後通過矽膠柱層析純化殘餘物，得到產物(7.6 g，11.8 mmol，66％)。
EX1的合成
Figure 02_image170
將中間體C(第一反應物)與100 ml的四氫呋喃(THF)混合物置於置於氮氣下，然後在-78o C下攪拌。在逐滴加入2.5M正丁基鋰(n-BuLi)的正己烷溶液(3.4 mL)之後，攪拌該混合物1小時。隨後，將溶於15 ml四氫呋喃(THF)的1.17 g (6.5 mmol)9-芴酮 (9H-fluoren-9-one；第二反應物) 緩滴加入，溫度慢慢回到室溫，且將混合物攪拌12小時。加入70 ml飽和碳酸氫鈉(NaHCO3 )後，反應完成，將混合物以DCM萃取，以接收有機層。然後用無水硫酸鎂乾燥，在真空下移除溶劑。將殘餘物溶解在30 ml醋酸，並加入少量的3 N鹽酸(HCl)。在100℃下攪拌12小時後，，使混合物冷卻至室溫並過濾。加入150 ml的硝基甲烷。隨後，分離有機層，然後在真空下移除溶劑。使濾液通過矽膠柱層析純化，得到產物 (2.6 g，3.4 mmol，52%)。MS(m/z，EI+ )：760.3。 實施例2
EX6的合成
Figure 02_image172
使用與合成EX1相類似的合成過程，不同之處在於，是用0.77 g (4.0 mmol)的雙噻吩環戊烷酮(Cyclopentadithiophene Ketone；第二反應物)而不是用9-芴酮 (9H-fluoren-9-one)，得到1.2 g (40%)的EX6。MS(m/z，EI+ )：772.2。 實施例3
甲基2-((9,9-二甲基-9H-芴-2-基)胺基)苯甲酸(methyl 2-((9,9-dimethyl-9H-fluoren-2-yl)amino)-benzoate)的合成
Figure 02_image174
將10 g (36.6 mmol)的2-溴-9,9-二甲基-9H-芴、6.64 g (43.9 mmol)的甲基2-鄰氨基苯甲酸、0.3 g (1.46 mmol)的乙酸鈀(Pd(OAc)2 )、17.9 g (54.9 mmol)的碳酸銫(CS2 CO3 )、及120 ml 的鄰二甲苯(o-Xylene)，五者脫氣並置於氮氣下，然後加熱回流12小時。在反應完成後，可以讓混合物冷卻至室溫。隨後，減壓以將溶劑從有機層移除，用柱層析純化粗產物，得到10 g的黃色油狀甲基2-((9,9-二甲基-9H-芴-2-基)胺基)苯甲酸(79.6 %)。1 H NMR (CDCl3 ，400 MHz)：化學位移(ppm) 8.97(s, 1H), 8.11(d, 1H), 7.87(d, 1H), 7.75-7.64(m, 3H), 7.41-7.29(m, 3H), 7.08(m, 1H), 6.92(d, 1H), 6.77(d, 1H), 3.79(s, 3H), 1.57(s, 3H) , 1.54(s, 3H)。
2-(2-((9,9-二甲基-9H-芴-2-基)胺基)苯基)-丙烷-2-醇(2-(2-((9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)- propan-2-ol)的合成
Figure 02_image176
將甲基2-((9,9-二甲基-9H-芴-2-基)胺基)苯甲酸(10 g，29.1 mmol)的化合物，與100 ml的四氫呋喃(THF)混合。對此混合物，在室溫下，慢慢加入58 ml，3M的甲基溴化鎂(CH3 MgBr)，接著在室溫下攪拌混合物3小時。在反應完成後，加入氯化銨溶液，得到反應混合物。然後，用乙酸乙酯/水進行萃取，分離出有機層。減壓以將溶劑從有機層移除，用柱層析純化粗產物，得到9 g的黃色油狀2-(2-((9,9-二甲基-9H-芴-2-基)胺基)苯基)-丙烷-2-醇(90 %)。1 H NMR (CDCl3 ，400 MHz)：化學位移(ppm) 8.91(s, 1H),7.81(d, 1H), 7.59(d, 1H), 7.54(d, 1H), 7.35-7.39(m, 3H), 7.29(m, 1H), 6.92(m, 1H), 6.76-6.74(d, 2H), 6.58(d, 1H), 3.88(s, 1H), 1.53(s, 3H) , 1.51(s, 3H) , 1.35(s, 6H)。
7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b]-吖啶(7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno-[1,2-b]-acridine)的合成
Figure 02_image178
將化合物2-(2-((9,9-二甲基-9H-芴-2-基)胺基)苯基)-丙-2-醇(2-(2-((9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-propan-2-ol) 27 g (78.6 mmol)與400 ml的二氯甲烷(CH2 Cl2 )混合。對此，在室溫下，慢慢加入51 ml的甲基磺酸(CH3 SO3 H)和37 ml的磷酸(H3 PO4 )，得到混合物。接著在室溫下攪拌混合物12小時。反應完成後，加入冰水(ice-cold water)，得到反應混合物。隨後，將20 %氫氧化鈉溶液加入混合物，然後用乙酸乙酯/水進行萃取，分離出有機層。減壓將溶劑從有機層移除。用柱層析純化粗產物，得到15 g的黃色固體狀7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b] 吖啶(58.8％)。1 H NMR (CDCl3 ，400 MHz)：化學位移(ppm) 8.95(s, 1H),7.79(s, 1H), 7.72(d, 1H), 7.43(d, 1H), 7.36(d, 1H), 7.25(m, 1H), 7.16(dd, 1H), 7.04(m, 1H), 6.87(s, 1H),6.81-6.78(m, 2H) 1.55(s, 6H), 1.38(s, 6H)。
中間體D的合成
Figure 02_image180
使用與合成中間體A相同的合成過程，不同之處在於，是用4,6-二溴硫茚(4,6-dibromobenzothiophene)(6.8 g，20 mmol)而不是用4,6-二溴苯並呋喃，是用7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b]-吖啶(6.5 g，20 mmol)而不是用雙(4-叔丁基苯基)胺，得到8.3 g (71%)的中間體D。
中間體E的合成
Figure 02_image182
使用與合成中間體B相同的合成過程，不同之處在於，是用中間體D(8.3 g，14.2 mmol)而不是用中間體A，得到5.7 g (73%)的中間體E。
中間體F的合成
Figure 02_image184
使用與合成中間體C相同的合成過程，不同之處在於，是用中間體E(5.7 g，10.3 mmol)而不是用中間體B，得到4.6 g (61%)的中間體F。
EX9的合成
Figure 02_image186
使用與合成EX1相同的合成過程，不同之處在於，是用中間體F (3.6 g, 4.8 mmol的第一反應物)而不是用中間體C，得到2.0 g (51%)的EX9。MS(m/z，EI+ )：820.4。 實施例4
EX10的合成
Figure 02_image188
使用與合成EX1相同的合成過程，不同之處在於，是用中間體F (3.6 g, 4.8 mmol的第一反應物)而不是用中間體C，得到2.5 g (48%)的EX10。MS(m/z，EI+ )：832.3。 實施例5
甲基2-(二苯並[b,d]呋喃-3-基氨基)苯甲酸(methyl 2-(dibenzo[b,d]thiophen-3-ylamino)benzoate)的合成
Figure 02_image190
將5 g (19 mmol)的3-二苯並[b,d]呋喃、3.45 g (22.8 mmol)的甲基2-鄰氨基苯甲酸、0.17 g (0.76 mmol)的乙酸鈀(Pd(OAc)2 )、9.28 g (28.5 mmol)的碳酸銫(CS2 CO3 )、及60 ml 的鄰二甲苯(o-Xylene)混合物脫氣並置於氮氣下，然後加熱回流12小時。在反應完成後，可以讓混合物冷卻至室溫。隨後，減壓以將溶劑從有機層移除，用柱層析純化粗產物，得到4.8 g的黃色油狀甲基2-(二苯並[b,d]呋喃-3-基氨基)苯甲酸 (75.8 %)。1 H NMR (CDCl3 ，400 MHz)：化學位移(ppm) 8.99(s, 1H),8.14(d, 1H), 7.89(d, 1H), 7.79-7.68(m, 3H), 7.45-7.33(m, 3H), 7.12(m, 1H), 6.97(d, 1H), 6.81(d, 1H), 3.79(s, 3H)。
2-(2-(二苯並[b,d]呋喃-3-基氨基)苯基)-丙烷-2-醇(2-(2-(dibenzo[b,d]thiophen-3-ylamino)phenyl)propan- 2-ol)的合成
Figure 02_image192
將甲基2-(二苯並[b,d]呋喃-3-基氨基)-苯甲酸(4.8 g, 14.4 mmol)的化合物，與50 ml的四氫呋喃(THF)混合。對此混合物，在室溫下，慢慢加入28 ml，3M的甲基溴化鎂(CH3 MgBr)，接著在室溫下攪拌混合物3小時。在反應完成後，加入氯化銨溶液，得到反應混合物。然後，用乙酸乙酯/水進行萃取，分離出有機層。減壓以將溶劑從有機層移除，用柱層析純化粗產物，得到4.5 g的黃色油狀2-(2-(二苯並[b,d]呋喃-3-基氨基)苯基)-丙烷-2-醇(93.7 %)。1 H NMR (CDCl3 ，400 MHz)：化學位移(ppm) 8.94(s, 1H),7.83(d, 1H), 7.62(d, 1H), 7.55(d, 1H), 7.41-7.36(m, 3H), 7.29(m, 1H), 6.94(m, 1H), 6.78-6.75(d, 2H), 6.59(d, 1H), 3.91(s, 1H), 1.35(s, 6H)。
中間體G的合成
Figure 02_image194
使用與合成中間體A相同的合成過程，不同之處在於，是用1,8-二溴-9,9-二甲基-9H-芴(1,8-dibromo-9,9-dimethyl-9H-fluorene) (7.0 g, 20 mmol)而不是用4,6-二溴苯並呋喃，是用12,12-二甲基-7,12-二氫苯並[4,5]噻吩[3,2-b]-吖啶(6.3 g, 20 mmol)而不是用雙(4-叔丁基苯基)胺，得到7.6 g (65%)的中間體G。
中間體H的合成
Figure 02_image196
使用與合成中間體B相同的合成過程，不同之處在於，是用中間體G(7.6 g, 13 mmol)而不是用中間體A，得到4.9 g (69%)的中間體H。
5,6-二溴-1,2-二氫苊烯的合成
Figure 02_image198
將70 g (460 mmol)的苊烯(Acenaphthylene)以及100 ml二甲基甲醯胺(DMF)的混合物置於氮氣下，並在0o C下攪拌。在逐滴加入180 g (1012 mmol)的N-溴代丁二醯亞胺(N-bromosuccinimide，NBS)的300ml二甲基甲醯胺(DMF)溶液之後，溫度回升至室溫，並攪拌該混合物18小時。將沉澱的產物，抽氣過濾，並用乙醇洗滌，將殘餘物從乙醇再結晶，得到產物(47 g，151.8 mmol，33%)。
中間體I的合成
Figure 02_image200
將3.1 g(10 mmol)的5,6-二溴-1,2-二氫苊、4.9 g(10 mmol)的中間體B、0.58 g(0.5 mmol)的四(三苯基磷)鈀(Pd(PPh3 )4 )、7 ml 2M的碳酸鉀(K2 CO3 )、40 ml的乙醇(EtOH)、及40 ml甲苯的混合物脫氣並置於氮氣下，然後在90℃下加熱過夜。反應完成後，使混合物冷卻至室溫。用乙酸乙酯和水分離並洗滌出有機層。用無水硫酸鎂乾燥後，在真空中除去溶劑。然後通過矽膠柱層析純化殘餘物，得到產物(7.6 g，11.8 mmol，66％)。
EX95的合成
Figure 02_image202
使用與合成EX1相同的合成過程，不同之處在於，是用中間體I(4.1 g, 5.6 mmol的第一反應物)而不是用中間體C，且是用4,5-二氮芴-9-酮(4,5-Diazafluoren-9-one)(1.0 g，5.6 mmol的第二反應物)而不是9-芴酮 (9H-fluoren-9-one)，得到1.6 g (35%)的EX95。MS(m/z，EI+ )：818.3。 實施例6
中間體J的合成
Figure 02_image204
使用與合成中間體A相同的合成過程，不同之處在於，是用6.7 g (20 mmol)的N,9-二苯基-9H-咔唑-2-胺(N,9-diphenyl-9H-carbazol-2-amine)而不是用4,6-二溴苯並呋喃，得到6.8 g (59%)的中間體J。
中間體K的合成
Figure 02_image206
使用與合成中間體B相同的合成過程，不同之處在於，是用中間體J 6.8 g (11.8 mmol)而不是用中間體A，得到4.8 g (75%)的中間體K。
中間體L的合成
Figure 02_image208
使用與合成中間體C相同的合成過程，不同之處在於，是用4.8 g (8.8 mmol)的中間體K而不是用中間體B，得到4.0 g (62%)的中間體L。
EX21的合成
Figure 02_image210
使用與合成EX1相同的合成過程，不同之處在於，是用4.0 g (5.5 mmol)的中間體L(第一反應物)而不是用中間體C，得到1.9 g (35%)的EX21。MS(m/z，EI+ )：813.3。 實施例7
EX23的合成
Figure 02_image212
使用與合成EX1相同的合成過程，不同之處在於，是用4.0 g (5.5 mmol)的中間體L(第一反應物)而不是用中間體C，且用1.0 g (5.5 mmol)的雙噻吩環戊烷酮(Cyclopentadithiophene Ketone；第二反應物)而不是用9-芴酮 (9H-fluoren-9-one)，得到2.1 g (47%)的EX23。MS(m/z，EI+ )：825.2。 生產有機電激發光組件的一般方法
提供阻值為9~12歐姆/平方(ohm/square)及厚度為120~160 nm的銦錫氧化物塗層玻璃(以下稱為ITO基板)，並在超聲波浴(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，通過紫外光(UV)和臭氧進一步處理清洗過的ITO基板。ITO基板的所有前處理工藝皆在潔淨室(100級)內進行。
在高真空設備(例如：電阻加熱的石英舟，10-7 Torr)中通過氣相沉積將這些有機層依序塗布到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多於一種化合物(即通常摻雜有摻雜材料的主體材料)，此可通過來自兩個或更多個來源的共氣相沉積成功地實現，表示本發明的化合物具有熱穩定性。
在此有機電致發光組件中使用二吡嗪並[2,3-f:2,3-]喹喔啉-2,3,6,7,10,11-六腈(dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11- hexacarbonitrile)(HAT-CN)作為電洞注入層。N,N-雙(萘-1-基)-N,N-雙(苯基)-聯苯胺(NPB)最常用來作為電洞傳輸層。10,10-二甲基-13-(3-(芘-1-基)苯基)-10H-茚並[2,1-b]三亞苯 (10,10-dimeth-yl-13-(3-(pyren-1-yl)phenyl)-10H-indeno [2,1-b]triphenylene) (H1)、10,10-二甲基-12-(4-(芘-1-基)苯基)-10H-茚並[2,1-b]三亞苯 (10,10-dimethyl-12-(4- (pyren-1-yl)phenyl)-10H-indeno[2,1-b]triphenylene) (H2)、及10,10-二甲基-12-(10-(4-(萘-1-基)-苯基)蒽-9-基)-10H-茚並[2,1-b]三亞苯10,10-dimethyl-12-(10-(4-(naphthalene-1-yl)-phenyl)anthracen-9-yl)-10H-indeno[2,1-b]triphenylene (H3)可用來作為有機 EL 組件中的發光主體 (emitting host)，且N1,N1,N6,N6-四-甲苯芘- 1,6-二胺(D1)可作為藍光摻雜(blue dopant)，以進行對照比較。使用HB3(參見下列化學結構)作為電洞阻擋材料(HBM)，並使用2-(10,10-二甲基-10氫-茚並[2,1-b]三伸苯-12-基)-4,6-二苯基-1,3,5-三嗪(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,6-diphenyl-1,3,5-triazine)(ET2)作為電子傳輸材料，以在有機EL組件中與8-羥基喹啉-鋰(8-hydroxyquinolato-lithium，LiQ)共沉積。本發明中用於製作對照與示例性有機EL組件的OLED材料、與本發明的示例性有機EL組件的化學結構，包括，但不限於：
Figure AA5
Figure AA6
有機EL組件通常包含通過熱蒸發形成作為陰極的低功函數金屬，例如Al、Mg、Ca、Li及K，且所述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提高有機EL組件性能。已知的電洞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、LiQ、MgO或Li2 O。另一方面，在製作有機EL組件之後，通過使用PR650光譜掃描光譜儀測量EL光譜及CIE座標。此外，電流/電壓、發光/電壓及產率/電壓特性都使用吉時利(Keithley)2400可程式設計電壓電流源來檢測。在室溫(約25℃)及大氣壓下操作上述設備。 實施例8
使用與上述方法類似的過程製作具有下列組件結構(如圖1所示)的發螢光有機EL組件：ITO/HAT-CN(20 nm)/NPB(110 nm)/摻雜5%發光摻雜材料的發光主體 (30 nm)/HB3/摻雜50% LiQ的ET2(35 nm)/LiQ(1 nm)/鋁(Al；160 nm)。在圖1所示的組件中，將電洞注入層(HIL)20(HAT-CN)沉積到透明電極10(ITO)上，將電洞傳輸層30(NPB)沉積到電洞注入層20上，將螢光發光層40(發光主體)沉積到電洞傳輸層(HTL)30上，將電洞阻擋層50(HB3)沉積到螢光發光層40上，將電子傳輸層60(ET2)沉積到電洞阻擋層(HBL)50上，將電子注入層70(LiQ)沉積到電子傳輸層(ETL)60上，並將金屬電極80(Al)沉積到電子注入層70上。將該實施例的有機EL組件的I-V-B(1000 尼特亮度時)等測試報告舉例總結於下表1。 表1
Figure 108115754-A0304-0001
根據上述示例的有機EL組件(表1)的測試報告總結，可知用作發光顏色為藍色之有機EL組件的發光摻雜材料，表現出比現有技術的材料更佳的性能。舉例來說，本發明使用式(1)的雜芳族化合物作為發光摻雜材料，來與主體材料例如H1、H2、或H3搭配的有機EL組件，可具有更低的功耗、更高的發光電流效率、或更長的半衰期。
總而言之，本發明揭示了一種雜芳族化合物，可用作有機EL組件發光層的螢光摻雜材料。該雜芳族化合物可由下式(1)表示：
Figure AA7
 其中Ar1 及Ar2 獨立為具有4、5或6 (4至6)個環碳原子的芳基或雜芳基；Ar3 為具有5至6個環碳原子的環烷基、環烯基、或芳基；R1 及R2 獨立為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基；W表示二價橋並選自於由O、S、Se、CR8 R9 、NR10 和 SiR11 R12 組成的群組；X是不存在，或是二價橋並選自於由O、S、Se、CR8 R9 、NR10 和 SiR11 R12 組成的群組；A是不存在，或表示以下式(2)：
Figure 02_image004
式(2)， 其中Y可以表示二價橋並選自於由O、S、Se、CR13 R14 、NR15 和SiR16 R17 所組成的群組；R8 至R17 獨立為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基、或具有3至36個碳原子的經取代或未經取代雜芳基。
根據上述教導顯然可以作出許多的修改及變化。因此，應當瞭解的是，在本發明的範圍內，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方式，但對於本領域技術人員來說，顯而易見的，在不偏離欲單獨由本發明範圍限制的情況下，是可以對本發明作出許多修改，但不足以限制本發明。
10‧‧‧透明電極20‧‧‧電洞注入層30‧‧‧電洞傳輸層40‧‧‧發光層50‧‧‧電洞阻擋層60‧‧‧電子傳輸層70‧‧‧電子注入層80‧‧‧金屬電極
圖1為本發明的有機EL元件的一個實施方式。
10‧‧‧透明電極
20‧‧‧電洞注入層
30‧‧‧電洞傳輸層
40‧‧‧發光層
50‧‧‧電洞阻擋層
60‧‧‧電子傳輸層
70‧‧‧電子注入層
80‧‧‧金屬電極

Claims (10)

  1. 一種以下式(1)的雜芳族化合物：
    Figure 108115754-A0305-02-0047-1
     其中Ar1及Ar2獨立為具有4、5或6(4至6)個環碳原子的雜芳基或芳基；Ar3為具有5至6個環碳原子的環烷基、環烯基、或芳基；R1及R2獨立為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基；W表示二價橋並選自於由O、S、Se、CR8R9、NR10和SiR11R12組成的群組；X是不存在或是二價橋並選自於由O、S、Se、CR8R9、NR10和SiR11R12組成的群組；A是不存在，或表示以下式(2)：
    Figure 108115754-A0305-02-0047-2
     其中Y可以表示二價橋並選自於由O、S、Se、CR13R14、NR15和SiR16R17所組成的群組；R8至R17獨立為氫原子、具有1至36個碳原子的經取代或未經取代烷基、具有6至36個碳原子的經取代或未經取代芳基、具有6至36個碳原子的經取代或未經取代芳烷基、或具有3至36個碳原子的經取代或未經取代雜芳基。
  2. 如請求項1所述的雜芳族化合物，其中Ar1及Ar2獨立為
    Figure 108115754-A0305-02-0048-5
  3. 如請求項1所述的雜芳族化合物，其中Ar3為
    Figure 108115754-A0305-02-0048-6
    或
    Figure 108115754-A0305-02-0048-7
    。
  4. 如請求項1所述的雜芳族化合物，其中該化合物可以由以下式(3)至式(12)中的一個表示：
    Figure 108115754-A0305-02-0048-3
    Figure 108115754-A0305-02-0049-4
  5. 如請求項1所述的雜芳族化合物，其中該雜芳族化合物為以下化合物中之一化合物：
    Figure 108115754-A0305-02-0049-8
    Figure 108115754-A0305-02-0050-10
    Figure 108115754-A0305-02-0051-11
    Figure 108115754-A0305-02-0052-12
    Figure 108115754-A0305-02-0053-13
    Figure 108115754-A0305-02-0054-14
    Figure 108115754-A0305-02-0055-15
    Figure 108115754-A0305-02-0056-16
    Figure 108115754-A0305-02-0057-17
    Figure 108115754-A0305-02-0058-18
    Figure 108115754-A0305-02-0059-19
    Figure 108115754-A0305-02-0060-20
    Figure 108115754-A0305-02-0061-22
    Figure 108115754-A0305-02-0062-23
    Figure 108115754-A0305-02-0063-24
  6. 一種有機電激發光組件，包括由陰極和陽極組成的電極對、及在該電極對之間的發光層及一個或多個有機薄膜層，其中該發光層和該有機薄膜層中的至少一個包括如請求項1所述的雜芳族化合物。
  7. 如請求項6所述的有機電激發光組件，其中包括式(1)的雜芳族化合物的發光層為螢光摻雜材料。
  8. 如請求項6所述的有機電激發光組件，其中包括式(1)的雜芳族化合物的發光層發射藍色的螢光。
  9. 如請求項6所述的有機電激發光組件，其中該有機電激發光組件為發光面板。
  10. 如請求項6所述的有機電激發光組件，其中該有機電激發光組件為背光面板。
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