TWI635068B - 新穎化合物及包含其之有機電子裝置 - Google Patents

新穎化合物及包含其之有機電子裝置 Download PDF

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TWI635068B
TWI635068B TW106103015A TW106103015A TWI635068B TW I635068 B TWI635068 B TW I635068B TW 106103015 A TW106103015 A TW 106103015A TW 106103015 A TW106103015 A TW 106103015A TW I635068 B TWI635068 B TW I635068B
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廖良玓
謝淑珠
陳濟中
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彩豐精技股份有限公司
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Abstract

本發明揭示如以下化學式(I)所表示之新化合物： 其中，Ar1、Ar2、Ar3、Ar4、L、Q、G、n1、n2、m1、m2及q係如說明書之定義。此外，本發明也揭露一有機電子裝置，其中的有機層包含本發明新穎化合物。

Description

新穎化合物及包含其之有機電子裝置
本發明係關於一種新穎化合物以及使用其之有機電子裝置。
有機發光裝置(OLED device)已公知最初是由Eastman Kodak公司提出通過真空蒸鍍法所發明的。Kodak公司的Tang及VanSlyke將電子傳遞材料如Alq3設置在表面上形成有一芳香族二胺有機層的透明氧化銦錫玻璃(縮寫為ITO)之上，接著氣相沉積金屬電極在Alq3層之上後完成有機電致發光(EL)裝置。因為具有高亮度、反應速度快、重量輕、小巧、色彩真實、無視角差別、不須使用任何LCD背光板以及低耗能的緣故，上述的有機EL裝置現在變成新一代的照明裝置或顯示裝置。
近年來，一些如電子傳遞層及電洞傳遞層的中間層被添加在陰極及陽極之間以增加OLED的電流效率及功率效率。例如，一種如圖1所示的有機發光二極體(OLED)1’被設計成包含有：一陰極11’、一電子注入層13’、一發光層14’、一電洞傳遞層16’及一陽極18’。
近年來，為了有效率的增加OLED的發光性能，OLED製造商及研究人員已努力地開發不同的化合物，作為OLED的材料。然而，儘管已經開發了 各種化合物，目前磷光的OLED仍然無法有優異的發光效率及裝置生命期，據此，基於用於OLED的常規或商業材料仍有缺點，本申請的發明人已作出了巨大的努力以做出創造性的研究，並最終提供了新穎化合物供OLED使用。
本揭露之目的在於提供一種新穎化合物和包含其之有機電子裝置。
根據一或多個實施例，化合物由以下化學式(I)所表示： 其中，Ar1、Ar2、Ar3和Ar4各自獨立為氫、氘、經取代或未經取代C1-C20之烷基、經取代或未經取代C6-C40之芳基、經取代或未經取代C1-C40之雜環基、或經取代或未經取代之胺基；或Ar1和Ar2與其所鍵結的N原子一起形成經取代或未經取代C1-C40之雜環基；或Ar3和Ar4與其所鍵結的N原子一起形成經取代或未經取代C1-C40之雜環基；L和Q各自獨立為經取代或未經取代C6-C40之亞芳基；G為氘、經取代或未經取代C1-C20之烷基、經取代或未經取代C6-C40之芳基、經取代或未經取代C1-C40之雜環基，或經取代或未經取代之胺基；n1和n2各自獨立為0或1；m1和m2各自獨立為0、1或2，且m1和m2不同時為0；以及q為0、1或2。
根據一或多個實施例，一有機電子裝置包含：一第一電極；一第二電極；以及一有機層，設置於該第一電極與該第二電極間，其中該有機層包含上述化學式(I)之化合物。
本發明提供一種新穎化合物，當本發明化合物用於有機電子裝置時，可以提升該有機電子裝置之效率，尤其是，當本發明之新穎化合物作為有機發光裝置的材料時，可以進一步提升該有機發光裝置之發光效率。
1’‧‧‧有機發光二極體
11‧‧‧基板
12、18’‧‧‧陽極
13、13’‧‧‧電洞注入層
14、16’‧‧‧電洞傳遞層
15、14’‧‧‧發光層
16‧‧‧電子傳遞層
17‧‧‧電子注入層
18、11’‧‧‧陰極
21‧‧‧第一電極
22‧‧‧第二電極
23‧‧‧有機層
圖1係先前技術的OLED裝置示意圖。
圖2係本發明的OLED裝置示意圖。
圖3係本發明的有機太陽能電池裝置示意圖。
圖4係本揭露之化合物(1)(SGM 178)之NMR圖譜。
圖5係本揭露之化合物(2)(SGM 179)之NMR圖譜。
圖6係本揭露之化合物(3)(SGM 180)之NMR圖譜。
圖7係本揭露之化合物(4)(SGM 181)之NMR圖譜。
圖8係本揭露之化合物(5)(SGM 182)之NMR圖譜。
圖9係本揭露之化合物(6)(SGM 271)之NMR圖譜。
圖10係本揭露之化合物(8)(SGM 271)之NMR圖譜。
圖11係本揭露之化合物(9)(SGM 436)之NMR圖譜。
圖12係本揭露之化合物(10)(SGM 437)之NMR圖譜。
圖13係本揭露之化合物(11)(SGM 438)之NMR圖譜。
圖14係本揭露之化合物(12)(SGM 439)之NMR圖譜。
圖15係本揭露之化合物(13)(SGM 273)之NMR圖譜。
圖16係本揭露之化合物(15)(SGM 116)之NMR圖譜。
圖17係本揭露之化合物(16)(SGM 175)之NMR圖譜。
圖18係本揭露之化合物(17)(SGM 176)之NMR圖譜。
圖19係本揭露之化合物(18)(SGM 177)之NMR圖譜。
圖20係本揭露之化合物(19)(SGM 542)之NMR圖譜。
圖21係本揭露之化合物(21)(SGM 563)之NMR圖譜。
圖22係本揭露之化合物(23)(SGM 562)之NMR圖譜。
圖23係本揭露之化合物(24)(SGM 575)之NMR圖譜。
以下將詳細描述本發明。本揭露以說明性的方式進行對發明的描述，所使用的術語應被理解為旨在描述而不在限制。對於本揭露的許多修飾和改變根據教示是可能的。因此，在所附權利要求的範圍內，本發明或許可以透過不同於具體描述之方式被實施。
化合物
根據一例示性實施例之化合物可以下列化學式(I)所表示。
在化學式(I)中，Ar1、Ar2、Ar3和Ar4可各自獨立為氫、氘、經取代或未經取代C1-C20之烷基、經取代或未經取代C6-C40之芳基、經取代或未經取 代C1-C40之雜環基、或經取代或未經取代之胺基；或Ar1和Ar2與其所鍵結的N原子一起可形成經取代或未經取代C1-C40之雜環基；或Ar3和Ar4與其所鍵結的N原子一起可形成經取代或未經取代C1-C40之雜環基；L和Q可各自獨立為經取代或未經取代C6-C40之亞芳基；G可為氘、經取代或未經取代C1-C20之烷基、經取代或未經取代C6-C40之芳基、經取代或未經取代C1-C40之雜環基、或經取代或未經取代之胺基；n1和n2各自獨立為0或1；m1和m2各自獨立為0、1或2，且m1和m2不同時為0；以及q為0、1或2。
根據一實施例，Ar1、Ar2、Ar3和Ar4可各自獨立為經取代或未經取代C6-C40之芳基、或經取代或未經取代C1-C40之雜環基；或Ar1和Ar2與其所鍵結的N原子一起可形成經取代或未經取代C1-C40之雜環基；或Ar3和Ar4與其所鍵結的N原子一起可形成經取代或未經取代C1-C40之雜環基。優選地，Ar1、Ar2、Ar3和Ar4各自獨立為經取代或未經取代C6-C40之芳基、或經取代或未經取代C1-C40之雜芳基；或Ar1和Ar2與其所鍵結的N原子一起形成經取代或未經取代C1-C40之雜芳基；或Ar3和Ar4與其所鍵結的N原子一起形成經取代或未經取代C1-C40之雜芳基。
根據一實施例，Ar1、Ar2、Ar3和Ar4可各自獨立為經取代或未經取代之苯基、經取代或未經取代之聯苯基、經取代或未經取代之聯三苯基、經取代或未經取代之茀基、經取代或未經取代之三苄基氧雜環庚烯基(tribenzyloxepinyl)、經取代或未經取代之二苯並呋喃基(dibenzofuranyl)、經取代或未經取代之二苯並噻吩基(dibenzothiofuranyl)、經取代或未經取代之萘基、或 經取代或未經取代之三苄基-氮呯基(tribenzyl-azepinyl group)。優選地，Ar1、Ar2、Ar3和Ar4各自獨立為未經取代之苯基、經烷基取代之苯基、未經取代之聯苯基、未經取代之聯三苯基、未經取代之茀基、經烷基取代之茀基、未經取代之三苄基氧雜環庚烯基、未經取代之二苯並呋喃基、或未經取代之萘基。
根據一實施例，m1可為1；且m2可為0或1。根據另一實施例，m1可為1，而m2可為0。根據再一實施例，m1可為1，而m2可為1。
根據一實施例，m1可為1；m2可為0；且Ar1和Ar2與其所鍵結的N原子一起可形成經取代或未經取代C1-C40之雜芳基。優選地，Ar1和Ar2與其所鍵結的N原子一起形成未經取代之三苄基-氮呯基(tribenzyl-azepinyl group)。
根據一實施例，當m1及m2不同時為0，-Ln1-NAr1Ar2及-Qn2-NAr3Ar4可相同。
根據一實施例，m1及m2為1，，-Ln1-NAr1Ar2及-Qn2-NAr3Ar4可相同。
根據一實施例，L和Q可以各自獨立為經取代或未經取代之亞苯基、亞聯苯基或亞萘基。優選地，L和Q各自獨立為未經取代之亞苯基。
根據一實施例，q可為0或1。
當q為1時，G可以為經取代或未經取代C6-C40之芳基、或經取代或未經取代C1-C40之雜環基。優選地，G為經取代或未經取代C6-C40之芳基、或包含一氮原子之經取代或未經取代C1-C40之雜芳基。更優選地，G為經取代或未經取代苯基，或未經取代之吡啶基。
根據一實施例，G、-Ln1-NAr1Ar2及-Qn2-NAr3Ar4可相同或不同。例如，當m1為1、m2為1而q為1時，-Ln1-NAr1Ar2及-Qn2-NAr3Ar4可相同，且G與-Ln1-NAr1Ar2及-Qn2-NAr3Ar4不同。
根據一實施例，該化學式(I)所示之化合物可為以下化學式(I-1)至(I-6)任一者所表示：
其中，化學式(I-1)至(I-6)中的Ar1、Ar2、Ar3、Ar4、L、Q、G、n1和n2係與以上描述相同。
根據一實施例，-Ln1-NAr1Ar2及-Qn2-NAr3Ar4可各自獨立選自由下列所組成之群組： 及；其中，*代表鍵結位置；Ra及Rb各自獨立為C1-20烷基；以及x及y各自 獨立為1或2。在此，Ra及Rb可相同。x及y可相同。Ra及Rb之例子可為甲基、乙基或丙基。此外，n1或n2可為0。
根據一實施例，n1為0而n2為1。根據另一實施例，n1為1而n2為1。於此兩個實施例中，-Ln1-NAr1Ar2及-Qn2-NAr3Ar4可各自獨立選自由下列所組成之群組： 、、以及；其中，*代表鍵結 位置。Ra、Rb、x及y之定義如前所述。於此兩個實施例中，L及Q可各自獨立為經取代或為取代之C6-C40亞芳基，如亞苯基。
以下，將詳細描述化學式(I)之取代基，本揭露未定義之取代基表示與本領域已知之定義相同。
在本發明中，該未經取代之烷基可以為線型或支鏈型，例如包含C1-C20之烷基、C1-C10之烷基或C1-C6之烷基。未經取代的烷基的具體例子包含甲基、乙基、正丙基、異丙基、正丁基、仲丁基、異丁基、叔丁基、戊基、新戊基或己基，但不侷限於此。在此，該未經取代之烷基至少一個氫原子可以被鹵素、烷基、烯基、烷氧基、環烷基、芳基、芳烷基、芳烯基、雜環基、氰基或乙炔基所取代。
在本揭露中，該未經取代之芳基是指芳香族烴基，例如可為C6-C40之芳基或C6-C20之芳基。此外，該芳基可為單環、雙環、三環或多環芳香族烴基； 其中二或多環可以彼此稠合或藉由單一鍵彼此相聯。未經取代之芳基的具體例子包含苯基、聯苯基、聯三苯基、聯四苯基、萘基、蒽基、苯並蒽基(benzanthryl)、菲基(phenanthryl)、稠四苯基(naphthacetyl)、芘基(pyrenyl)、屈基(chrysenyl)、苯並[c]菲基、苯並[g]屈基、三亞苯基、芴基(fluorenyl)、螺環雙芴基(spirobifluorenyl)、苯並芴基(benzofluorenyl)或二苯並芴基(dibenzofluorenyl)，但不侷限於此。在此，該未經取代之芳基至少一個氫原子可被以上關於烷基描述之相同取代基取代。此外，該亞芳基之定義與以上敘述相同，且不在此詳細說明。
在本發明中，該未經取代之雜環基是指非芳香族或芳香族烴基，例如可為C1-C40之雜環基、C2-C20之雜環基或C4-C20之雜環基。此外，該雜環基可為具有至少一選自O、N、及S之雜原子之單環、雙環、三環或多環雜芳基或雜環烷基；其中二或多環可以彼此稠合或藉由單一鍵彼此相聯。未經取代之雜環基之具體例子包含吡咯基(pyroryl)、吡嗪基(pyrazinyl)、吡啶基、哌啶基、吲哚基、異吲哚基、咪唑基、苯並咪唑基、呋喃基、噁唑基(ozazolyl)-、噻唑基、噻二唑基(thiadiazolyl)、苯並噻唑基、四唑基、噁二唑基(oxadiazolyl)、三吖嗪基(triazinyl)、咔唑基、苯並呋喃基、二苯並呋喃基、二苯並噻吩基(dibenzothiofuranyl)、二苯並苯硫基(dibenzothiophenyl)、喹啉基、異喹啉基、喹喔啉基(quinoxalinyl)、菲唳基(phenantridinyl)、吖啶基(acridinyl)、菲咯啉基(phenanthrolinyl)、吩嗪基(phenazinyl)、啡噻嗪基(phenothiazinyl)、吩惡嗪基(phenoxazinyl)、噁唑基(oxazolyl)、噁二唑基(oxadiazolyl)、呋咱基(furazanyl)、噻吩基(thienyl)、苯並苯硫基(benzothiophenyl)、三苯基氧呯基(tribenzyloxepinyl)、苯硫基(thiophenyl)或苯並噁唑基(benzooxazolyl)，但不侷限 於此。在此，該未經取代之雜環基至少一氫原子可被以上關於烷基描述之相同取代基取代。
在本發明中，鹵素包含氟、氯、溴和碘；優選為氟或溴。
在本發明中，該未經取代之烷氧基是指上述定義之烷基與氧原子偶合的基團。例如可以包含線型或支鏈型C1-C10之烷氧基或線型或支鏈型C1-C6之烷氧基。具體例子包含甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、仲丁氧基、叔丁氧基、戊氧基、新戊氧基或己氧基，但不侷限於此。在此，該未經取代之烷氧基至少一氫原子可被以上關於烷基描述之相同取代基取代。
在本發明中，該未經取代之環烷基是指具有3-20個碳原子的單價飽和烴環，或3-12個碳原子的單價飽和烴環。未經取代之環烷基之具體例子包含環丙基、環丁基、環戊基、環己基、環庚基或環辛基，但不侷限於此。在此，該未經取代之環烷基至少一氫原子可被以上關於烷基描述之相同取代基取代。
在本發明中，該未經取代之烯基可以為線型或支鏈型，且具有至少一個碳-碳雙鍵。例如可以包含C1-C20之烯基、C1-C10之烯基或C1-C6之烯基。未經取代之烯基之具體例子包含乙烯基、丙烯基、丙亞烯基、烯丙基或1,4-丁二烯，但不侷限於此。在此，該未經取代之烯基至少一氫原子可被以上關於烷基描述之相同取代基取代。
化學式(I)所示之化合物可以包含下列化合物(1)至(122)任一者： 在此，化合物(1)-(122)中的至少一個氫原子可以進一步選擇性地被上述取代基取代。
有機電子裝置
本發明提供一包含上述化合物之有機電子裝置。
在一實施例中，該有機電子裝置包含：一第一電極；一第二電極以及一設置於上述第一電極與第二電極之間的有機層，其中，該有機層包含上述化合物中之任一者。
在此，「有機層」是指單層或多層，其設置於有機電子裝置之第一電極與第二電極之間。
本發明之有機電子裝置的應用包括但不限於有機發光裝置、有機太陽能電池裝置、有機薄膜電晶體、有機光感測器、平板顯示器、電腦顯示器、電視、廣告牌、室內或室外照明光、室內或室外信號光、抬頭顯示器、全透明顯示器、可撓式顯示器、雷射印表機、電話、手機、平板電腦、筆記型電腦、數位相機、便攜式攝像機、取景器、微型顯示器、交通工具、大電視牆、劇場 或體育場屏幕、信號標誌。較佳地，本揭露之有機電子裝置應用在有機發光裝置或有機太陽能電池裝置中。
在一實施例中，有機電子裝置可為有機發光裝置，圖2為本發明中之一實施例使用的有機發光裝置的示例性結構示意圖，如圖2所示，該有機發光裝置包含：一基板11；一陽極12；一陰極18；以及一有機層包含一電洞注入層13、一電洞傳遞層14、一發光層15、一電子傳遞層16和一電子注入層17。然而，本發明並不侷限於此。可以在本發明的有機發光裝置中形成能夠提高有機發光裝置之發光效率的其他層，例如一電子阻隔層或一電洞阻隔層。當本發明之有機發光裝置進一步包含電子阻隔層時，該電子阻隔層設置於電洞傳遞層14與發光層15之間。當本發明之有機發光裝置進一步包含電洞阻隔層時，該電洞阻隔層設置於電子傳遞層16與發光層15之間。
在一實施例中，本發明之有機發光裝置可以包含一含有上述化合物之電洞傳遞層。在另一實施例中，本發明之有機發光裝置可以包含一含有上述化合物之電洞注入層。在又一實施例中，本發明之有機發光裝置可以包含一含有上述化合物之電子阻隔層。然而，本發明並不侷限於此。
在一實施例中，發光層可以包含一含有銥或鉑的磷光發光材料。在另一實施例中，發光層可以包含一量子點或半導體奈米結晶材料。然而，本發明並不侷限於此。
在另一實施例中，有機電子裝置可為有機太陽能電池，圖3為本發明中之一實施例使用的有機太陽能電池的示例性結構示意圖，如圖3所示，該有機太陽能電池可包含：一第一電極21；一第二電極22；以及一設置於上述第 一電極21與第二電極22之間的有機層23，且有機層23包含上述化合物中之任一種。在此，該有機層23可以作為一載子傳遞層。
本發明之其他目的、優勢及新穎特徵可從下面的詳細描述結合附圖，變得更加清楚。
實施例
以下實施例是為了提供本發明特性之說明，然而本發明並不侷限於以下實施例之描述。
除非另有說明，否則以下合成是在保護氣體氣氛下執行。起始物可以從Aldrich或Alfa購得，或根據文獻所揭示的製程合成。
合成實施例1-中間物A1-A15及其合成
用於製備化學式(I)之化合物的中間物A1-A15列於以下表1中，其中，每個中間物下方的數字表示其CAS編號。
中間物A1-A10和A14-A15
中間物A1-A10和A14-A15從Aldrich或Alfa購買，且CAS編號列於上表。
中間物A11-A13之合成
中間物A11-A13可根據以上流程I來製備。起始物Ar1-NH2(芳基胺)和Br-Ar2(溴芳基)列於下表2中。
簡要地，將溴芳基(1.0eq)、芳基胺(1.05eq)、乙酸鈀(0.01eq)、1,1'-雙(二苯基膦)二茂鐵(dppf，0.04eq)、第三丁基氧化鈉(NaO-t-Bu，1.5eq)和甲苯之混合物置於圓底瓶中，於氮氣氣氛下加熱至80℃反應12小時，待反應完成後，於真空下移除揮發物，將剩餘之溶液以二氯甲烷萃取(3×60mL)，合併有機層以食鹽水洗，以硫酸鈉乾燥並濃縮後得黃色固體，進一步將粗產物以矽膠管柱層 析法純化，使用己烷/二氯甲烷混合物(體積比2：1)作為沖提液。所得產物即中間物A11-A14的分析數據列於下表2中。
合成實施例2-中間物B1-B4及其合成
用於製備化學式(I)之化合物的中間物B1-B4列於以下表3中。
中間物B1之合成
[流程II]
中間物B1可根據以上流程II來製備。
步驟1：中間物B1-1之合成
取3-溴二苯並[a,d]環庚-5-酮(86g，1.0eq)、N-溴琥珀醯亞胺(106g，2.0eq)和過氧化芐基(0.7g，0.01eq)溶於四氯化碳(430mL)，將混合物加熱至85℃，以HPLC監測反應，待反應完成後，過濾移除沉澱物並以甲醇洗，接著再結晶純化，純化後的產物濃縮至乾燥後得白色固體產物(123g，92.3%)。FD-MS分析C15H9Br3O：理論值444.94，實際值444.94。
步驟2：中間物B1-2之合成
取中間物B1-1(116.0g，1.0eq)溶於呋喃/四氫呋喃(體積比2/1，960ml)，將反應冷卻至0℃後加入第三級丁基氧化鉀(KO-t-Bu，87.8g，3.0eq)，反應於0℃下攪拌1小時再回溫至室溫攪拌12小時，待反應完成後，反應以去離子水終止反應，有機層以溶劑萃取回復並以硫酸鈉乾燥，從有機層中以減壓蒸餾移除溶劑，並將生成之殘餘物以矽膠管柱層析法純化，純化後之產物濃縮乾燥，得淺黃色固體產物(46.8g，51.1%)。FD-MS分析C19H11BrO2：理論值351.19，實際值351.19。
步驟3：中間物B1-3之合成
取中間物B1-2(53.5g，1.0eq)和5% Pd/C(8.1g，0.025eq)於乙酸乙酯(535ml)形成一懸浮液，反應在氫氣下攪拌3-6小時，生成之混合物以矽藻土過濾並以乙酸乙酯洗，減壓濃縮濾液後得黃色固體中間物B1-3(100g，100%)，中間物B1-3不經過進一步純化直接用於下一步反應。
步驟4：中間物B1之合成
取中間物B1-3(53g，1.0eq)和對甲苯磺酸(57g，2.0eq)於甲苯(530ml)下加熱至110℃反應12小時，將混合物冷卻至室溫後以飽和碳酸氫鈉水溶液終止反應，再以二氯甲烷萃取，有機層依序以水、食鹽水洗後，以無水硫酸鈉乾燥，減壓濃縮生成之溶液並以矽膠管柱層析法純化，使用二氯甲烷/己烷(體積比1/1)作為沖提液，得淺黃色固體中間物B1(46.0g，91.5%)。FD-MS分析C19H11BrO：理論值335.19，實際值335.19。
中間物B2-B4之合成
除了將製備中間物B1的3-溴二苯並[a,d]環庚-5-酮以製備中間物B2的2-溴二苯並[a,d]環庚-5-酮取代，以製備中間物B3的3,7-二溴二苯並[a,d]環庚-5-酮取代，或以製備中間物B4的苯並[a,d]環庚烯-5-酮取代外，中間物B2-B4之合成步驟與製備中間物B1之方法相似，所有步驟的中間物、產率和質譜分析數據列於下表4中。
中間物B4之合成
中間物B4可根據以上流程III來製備。
取中間物B3(1.0eq)、中間物A1(2.1eq)、乙酸鈀(0.01eq)、四氟硼酸三叔丁基磷(0.02eq)和叔丁基氧化鈉(1.5eq)溶於甲苯(0.3M)中，將混合物加熱至90℃反應12小時，待反應完成後，在真空下移除蒸發物，並將剩餘溶液以二氯甲烷萃取(3×60mL)，合併有機萃取物以食鹽水洗，硫酸鈉乾燥並濃縮剩下黃色固體，進一步將粗產物以矽膠管柱層析法純化，獲得黃色固體中間物B4(83%)。 合成實施例3-中間物C1-C7及其合成
用於製備化學式(I)之化合物的中間物C1-C7列於以下表5中。
中間物C1之合成
中間物C1可根據以上流程IV來製備。
步驟1：螺環醇之合成
取2-溴二苯基(46g，1eq)溶於無水四氫呋喃(0.3M)在-78℃下攪拌，逐滴加入正丁基鋰(79mL，2.5M，1.0eq)。攪拌20分鐘後，加入中間物 B1(46.3g，0.7eq)並將反應回溫至室溫，以HPLC監測反應，待反應完成後，以水洗反應溶液並將水層以乙酸乙酯萃取，合併有機層以飽和食鹽水洗，再以硫酸鎂乾燥，待乾燥後將混合物抽吸過濾並濃縮濾液，得到淺黃色螺環醇之粉狀固體(65g)，不須進一步純化直接用於步驟2。
步驟2：中間物C1之合成
於上述螺環醇(65g，1.0eq)中，加入乙酸(w/v=1/3的反應物)及硫酸(10滴)，於110℃下攪拌混合物6小時，以HPLC監測反應，待反應完成後以過濾分離沉澱物，以管柱層析法純化剩餘的物質，得白色固體中間物C1(58g，93.0%)。FD-MS分析C31H19Br：理論值471.39，實際值471.39。
中間物C2和C3之合成
除了將製備中間物C1的2-溴聯苯基中間物和中間物B以下表6的化合物取代，中間物C2和C3之合成步驟與製備中間物C1之方法相似，所得的中間物C2和C3為白色固體，此外，中間物C1-C3的產率和質譜分析數據列於下表6中。
中間物C4和C5之合成
步驟1：螺環醇之合成
除了將製備中間物C1的2-溴聯苯基中間物和中間物B以下表7的化合物取代，中間物C4和C5之合成步驟與製備中間物C1之方法相似。
步驟2：中間物C4和C5之合成
取螺環醇中間物(1.0eq)和對甲苯磺酸(2.0eq)溶於甲苯(螺環醇之10倍量)，將反應加熱回流12小時，反應混合物冷卻至室溫後以飽和碳酸氫鈉水溶液終止反應，並以二氯甲烷萃取，有機層依序以水、食鹽水洗，以無水硫酸鈉乾燥，接著在減壓條件下濃縮剩餘溶液，並以矽膠管柱層析法純化，得白色固體中間物C4和C5，此外，中間物C4和C5的產率和質譜分析數據列於下表7中。
中間物C6和C7之合成
中間物C6和C7可根據以上流程VI來製備。
取中間物C(1.0eq)、硼酸(1.1eq)、乙酸鈀(0.01eq)、三苯基膦(0.04eq)和3.0M碳酸鉀水溶液(1.5eq)溶於甲苯(0.4M)中，將反應加熱至100℃反應12小時，待完成反應後，以真空移除揮發物，並將剩餘的溶液以二氯甲烷萃取(3×60mL)，合併有機萃取物以食鹽水洗，硫酸鈉乾燥並濃縮留下黃色固體，進一步將粗產物以矽膠管柱層析法純化，此外，中間物C6和C7的產率和質譜分析數據列於下表8中。
合成實施例4-化合物(1)-(6)、(8)-(13)、(15)-(19)、(21)、(23)和(24) 化合物(1)-(6)、(8)-(13)、(15)-(19)、(21)、(23)和(24)之合成
本發明之化合物可根據以下流程VII或流程VIII來合成。
簡要地，取中間物C1-C3和C6-C7(1.0eq)、中間物A1-A13(1.05eq)、乙酸鈀(0.005eq)、四氟硼酸三叔丁基磷(P(t-Bu)3HBF4，0.02eq)和第三丁基氧化鈉(1.5eq)溶於甲苯(40mL)，將反應加熱至90℃反應12小時(藉由改變中間物A1-A13和催化劑的當量，可以區域選擇性的得到單-和雙-耦合產物)，待反應完成後，在真空下移除揮發物，並將殘餘溶液以二氯甲烷萃取(3×60mL)，合併有機萃取物以食鹽水洗，硫酸鈉乾燥並濃縮留下黃色固體，進一步將粗產物以矽膠管柱層析法純化，得到白色固體之最終產物。
簡要地，取中間物C4-C5(1.0eq)、中間物A14-A15(2.0eq)、三(二亞苄基丙酮)二鈀(Pd2(dba)3，0.01eq)、P(Cy)3HBF4(0.04eq)和磷酸鉀(3.0eq)溶於甲苯(40mL)，將混合物加熱至100℃反應12小時，待完成反應後，在真空下移除揮發物，並將殘餘溶液以二氯甲烷萃取(3×60mL)，合併有機萃取物以食鹽水洗，硫酸鈉乾燥並濃縮留下黃色固體，進一步將粗產物以矽膠管柱層析法純化，得到白色固體之最終產物。
產物(1)-(6)、(8)-(13)、(15)-(19)、(21)、(23)和(24)、所使用的中間物、產率及質譜分析數據列於下表9中。
實施例-OLED裝置製造
將一具有厚度為1500Å之ITO(氧化銦錫)塗層的玻璃基板放置於包含清洗劑的蒸餾水中，以超聲波洗滌，在此，該清洗劑是由Fischer Co.所製造，且蒸餾水是經過過濾器(Millipore Co.)二次過濾而得。ITO以清潔劑經過30分鐘清洗後，以蒸餾水進行2次超聲波清洗共10分鐘，接著以異丙醇、丙酮和甲醇溶劑超聲波清洗並乾燥，再將其轉移到等離子體清潔器(plasma cleaner)，接著以氧等離子體將該基板清潔5分鐘，並將其轉移至真空蒸發器。
各種有機材料和金屬材料依序沉積於ITO基板上而獲得本實施例之OLED裝置，在沉積期間，真空程度維持在1x10-6至3x10-7torr。此外，下述OLED裝置所使用的材料的化學式及代號，列於下表10中。
製備藍色OLED裝置
於製備本實施例之藍色OLED裝置時，首先將HAT沉積在ITO基板上，而得厚度為100Å的第一電洞注入層。再將摻雜有HAT(5.0wt%)的HI-2沉積於第一電洞注入層上，而得到厚度為750Å之第二電洞注入層。
接著，沉積HT-1或本揭露化合物而得到第一電洞傳遞層(HT1)，厚度為100Å；及/或沉積HT-2或本揭露化合物而得到第二電洞傳遞層(HT2)，厚度為100Å。
而後，將摻雜有BD(3.5wt%)的BH沉積在第一或第二電洞傳遞層上，而得到厚度為250Å的發光層。將摻雜有Liq(35.0wt%)的ET沉積在發光層上，而得到厚度為250Å的電子傳遞層。將Liq沉積於電子傳遞層上，得到厚度為15Å的電子注入層。將Al沉積在電子注入層上，而得到厚度為1500Å的陰極。
經由前述步驟，可得到下述測試例所使用的藍色OLED裝置。
製備綠色OLED裝置
綠色OLED裝置的製備與藍色OLED裝置的製備相似，除了第二電洞注入層、發光層及電子傳遞層不同外。
在此，第二電洞注入層厚度為1300Å。將摻雜有GD(10wt%)的GH沉積在電洞傳遞層上，而得到厚度為400Å的發光層。電子傳遞層厚度為350Å。
製備紅色OLED裝置
紅色OLED裝置的製備與藍色OLED裝置的製備相似，除了第二電洞注入層、發光層及電子傳遞層不同外。
在此，第二電洞注入層厚度為2100Å。將摻雜有RD(3.5wt%)的RH沉積在電洞傳遞層上，而得到厚度為300Å的發光層。電子傳遞層厚度為350Å。
OLED裝置測量
以PR-650測量所製得的藍色、綠色和紅色OLED裝置的裝置性能。以1000尼特(nit)收集藍色和紅色OLED裝置數據，以3000尼特(nit)收集綠色OLED裝置數據。數據如CIE、發光效率(Eff.)和驅動電壓(Voltage)列於下表11-13中。
根據表11-13的結果，使用化學式(I)所示之化合物的OLED裝置具有提升之發光效率以及低驅動電壓，因此，本發明之化學式(I)所示之化合物可以有效地用來作為OLED裝置的電洞傳遞材料。
雖然本發明已透過較佳實施例進行說明，應了解在不悖離本發明隨附申請專利範圍的精神及範圍的前提下，可對本發明作出許多可能的修飾及改變。

Claims (21)

  1. 一種如化學式(I)所示之化合物：其中，Ar1、Ar2、Ar3和Ar4各自獨立為氫、氘、經取代或未經取代C1-C20之烷基、經取代或未經取代之苯基、經取代或未經取代之聯苯基、經取代或未經取代之聯三苯基、經取代或未經取代之茀基、經取代或未經取代之三苄基氧雜環庚烯基、經取代或未經取代之二苯並呋喃基、經取代或未經取代之二苯並噻吩基、經取代或未經取代之萘基、或經取代或未經取代之三苄基-氮呯基；或Ar1和Ar2與其所鍵結的N原子一起形成經取代或未經取代C1-C40之雜環基；或Ar3和Ar4與其所鍵結的N原子一起形成經取代或未經取代C1-C40之雜環基；L和Q各自獨立為經取代或未經取代C6-C40之亞芳基；G為氘、經取代或未經取代C1-C20之烷基、經取代或未經取代C6-C40之芳基、經取代或未經取代C1-C40之雜環基、或經取代或未經取代之胺基；n1和n2各自獨立為0或1；m1和m2各自獨立為0、1或2，且m1和m2不同時為0；以及q為0、1或2。
  2. 如申請專利範圍第1項所述之化合物，其中，Ar1、Ar2、Ar3和Ar4各自獨立為未經取代之苯基、經烷基取代之苯基、未經取代之聯苯基、未經取代之聯三苯基、未經取代之茀基、經烷基取代之茀基、未經取代之三苄基氧雜環庚烯基、未經取代之二苯並呋喃基、或未經取代之萘基。
  3. 如申請專利範圍第1項所述之化合物，其中，m1為1；且m2為0或1。
  4. 如申請專利範圍第1項所述之化合物，其中，m1為1；m2為0；且Ar1和Ar2與其所鍵結的N原子一起形成經取代或未經取代C1-C40之雜芳基。
  5. 如申請專利範圍第4項所述之化合物，其中，Ar1和Ar2與其所鍵結的N原子一起形成未經取代之三苄基-氮呯基。
  6. 如申請專利範圍第1項所述之化合物，其中，L和Q各自獨立為經取代或未經取代之亞苯基、亞聯苯基或亞萘基。
  7. 如申請專利範圍第6項所述之化合物，其中，L和Q各自獨立為未經取代之亞苯基。
  8. 如申請專利範圍第1項所述之化合物，其中，q為0或1。
  9. 如申請專利範圍第1項所述之化合物，其中，q為1；且G為經取代或未經取代C6-C40之芳基或經取代或未經取代C1-C40之雜環基。
  10. 如申請專利範圍第9項所述之化合物，其中，G為經取代或未經取代C6-C40之芳基、或包含一氮原子之經取代或未經取代C1-C40之雜芳基。
  11. 如申請專利範圍第10項所述之化合物，其中，G為經取代或未經取代之苯基或未經取代之吡啶基。
  12. 如申請專利範圍第1項所述之化合物，其中，該化合物為以下化學式(I-1)至(I-6)任一者所表示： 其中，Ar1、Ar2、Ar3、Ar4、L、Q、G、n1、n2係與化學式(I)所示相同。
  13. 如申請專利範圍第1項所述之化合物，其中-Ln1-NAr1Ar2及-Qn2-NAr3Ar4各自獨立選自由下列所組成之群組： 其中，*代表鍵結位置；Ra及Rb各自獨立為C1-20烷基；以及x及y各自獨立為1或2。
  14. 如申請專利範圍第13項所述之化合物，其中n1或n2為0。
  15. 如申請專利範圍第1項所述之化合物，其中n1或n2為1，-Ln1-NAr1Ar2及-Qn2-NAr3Ar4各自獨立選自由下列所組成之群組： 、、以及；其中，*代表鍵結位置；Ra及Rb各自獨立為C1-20烷基；以及x及y各自獨立為1或2。
  16. 如申請專利範圍第1項所述之化合物，其中該化合物為下列化合物(1)至(122)任一者所表示：
  17. 一種有機電子裝置，包含：一第一電極；一第二電極；以及一有機層，設置於該第一電極與該第二電極間，其中該有機層包含如申請專利範圍第1項所述之化合物。
  18. 如申請專利範圍第17項所述之有機電子裝置，其中，該有機電子裝置為一有機發光裝置。
  19. 如申請專利範圍第18項所述之有機電子裝置，其中，該有機層包含一電洞傳遞層；且該電洞傳遞層包含如申請專利範圍第1項所述之化合物。
  20. 如申請專利範圍第18項所述之有機電子裝置，其中，該有機層包含一電洞注入層；且該電洞注入層包含如申請專利範圍第1項所述之化合物。
  21. 如申請專利範圍第18項所述之有機電子裝置，其中，該有機層包含一電子阻隔層；且該電子阻隔層包含如申請專利範圍第1項所述之化合物。
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