TW201726609A - 化合物及其有機電子裝置 - Google Patents

化合物及其有機電子裝置 Download PDF

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TW201726609A
TW201726609A TW106102571A TW106102571A TW201726609A TW 201726609 A TW201726609 A TW 201726609A TW 106102571 A TW106102571 A TW 106102571A TW 106102571 A TW106102571 A TW 106102571A TW 201726609 A TW201726609 A TW 201726609A
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TWI629257B (zh
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廖良玓
吳蕙玲
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

本發明提供一種化合物及其有機電子裝置，化合物如下式(I)所示，G1至G4中其中之一者為碳數小於或等於60且具有至少一氮原子的雜芳基、具有至少一官能基的環烷基、雜環烷基、芳香基、芳氧基、芳矽基或芳硼基；或者為碳數小於或等於40且具有至少一官能基的烷基、烯基、炔基、烷氧基、矽烷基、硼烷基、膦基或氧膦基；該官能基係選自於由氰基、硝基、氟基和氯基所構成的群組；G1至G4中其他者和G5分別獨立為經取代或未經取代的上述基團；h、i、j、k和l分別獨立為1至4的整數。□ 式(I)

Description

化合物及其有機電子裝置
本發明是關於一種新穎化合物以及一種使用其之有機電子裝置，尤指一種用於電子傳輸層的新穎化合物以及使用其之有機電子裝置。
隨著科技的進步，各種使用有機材料製成的有機電子裝置蓬勃發展，常見的有機電子裝置如有機發光二極體 (organic light emitting device，OLED)、有機光電晶體 (organic phototransistor)、有機光伏打電池 (organic photovoltaic cell)和有機光偵測器 (organic photodetector)。
OLED最初是由伊士曼柯達公司(Eastman Kodak)所發明並提出，伊士曼柯達公司的鄧青雲博士和Steven Van Slyke以真空蒸鍍法 (vacuum evaporation method)於形成有有機芳香二元胺電洞傳輸層的透明氧化銦錫 (indium tin oxide，ITO)玻璃上沉積一電子傳輸材料{例如三(8-羥基喹啉)鋁 [tris(8-hydroxyquinoline)aluminum(III)，簡稱為Alq3 ]}；再於電子傳輸層上沉積一金屬電極，即可完成OLED的製作。OLED因兼具反應速率快、質輕、薄形化、廣視角、亮度高、對比高、無需設置背光源以及低耗能的優點，因此備受關注，但OLED仍具有低效率和壽命短的問題。
為了克服低效率的問題，其中一種改善方式為於陰極和陽極間設置中間層，請參閱圖1所示，改良的OLED依序設置有一基板11、一陽極12、一電洞注入層13 (hole injection layer，HIL)、一電洞傳輸層14 (hole transport layer，HTL)、一發光層15 (an emitting layer，EL)、一電子傳輸層16 (electron transport layer，ETL)、一電子注入層17 (electron injection layer，EIL)和一陰極18。當於陽極12和陰極18施加一電壓時，由陽極12射出的電洞會穿過HIL和HTL並移動至EL，而由陰極18射出的電子會穿過EIL和ETL移動至EL，使電洞和電子在EL層重組成激子 (exciton)，當激子由激發態衰退返回基態時即可產生光線。
另一改善方式為改良OLED中ETL的材料，使電子傳輸材料展現出電洞阻擋能力，傳統的電子傳輸材料包括3,3′-[5′-[3-(3-吡啶基)苯基][1,1′:3′,1″-三聯苯]-3,3″-二基]二吡啶 {(3,3′-[5′-[3-(3-pyridinyl)phenyl][1,1′:3′,1″-terphenyl]-3,3″-diyl]bispyridine，TmPyPb}、1,3,5-三(1-苯基-1H-苯並咪唑-2-基)苯 [1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene，TPBi]、三(2,4,6-三甲基-3-(3-吡啶基)苯基)硼烷 [tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane，3TPYMB]、1,3-二(3,5-二吡啶-3-基-苯基)苯 [1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene，BmPyPb]和9,10-二(3-(3-吡啶基)苯基)蒽 [9,10-bis(3-(pyridin-3-yl)phenyl)anthracene，DPyPA]。
然而，即使使用了所述電子傳輸材料，OLED的電流效率仍具有可改善的空間，因此，本發明提供了一種新穎的化合物以克服傳統低電流效率的問題。
本發明的目的為提供一種新穎化合物，其可用於有機電子裝置。
本發明的另一目的為提供一種使用該新穎化合物的有機電子裝置，藉此降低有機電子裝置之驅動電壓。
再者，本發明的另一目的為提供一種使用該新穎化合物的有機電子裝置，藉此提升有機電子裝置之效率。
為達上述目的，本發明的新穎化合物具有式(I)： 於式(I)中，G1 至G4 其中之一是選自於由下列所構成的群組：具有至少一氮原子且碳數為3至60的雜芳基、具有至少一官能基且碳數為1至40的烷基、具有至少一官能基且碳數為2至40的烯基、具有至少一官能基且碳數為2至40的炔基、具有至少一官能基且碳數為3至60的環烷基、具有至少一官能基且碳數為3至60的雜環烷基、具有至少一官能基且碳數為1至40的烷氧基、具有至少一官能基且碳數為6至60的芳香基、具有至少一官能基且碳數為6至60的芳氧基 (aryloxy group)、具有至少一官能基且碳數為1至40的矽烷基 (alkylsilyl group)、具有至少一官能基且碳數為6至60的芳矽基 (arylsilyl group)、具有至少一官能基且碳數為1至40的硼烷基 (alkylboron)、具有至少一官能基且碳數為6至60的芳硼基 (arylboron group)、具有至少一官能基且碳數為1至40的膦基 (phosphine group)和具有至少一官能基且碳數為1至40的氧膦基 (phosphine oxide group)； 該官能基係選自於由氰基、硝基、三氟甲基 (trifluoromethyl group)、氟基和氯基所構成的群組； G1 至G4 中其他者和G5 係分別獨立選自於由下列所構成的群組：氫原子、氘原子、鹵基、氰基、硝基、三氟甲基、經取代或未經取代且碳數為1至40的烷基、經取代或未經取代且碳數為2至40的烯基、經取代或未經取代且碳數為2至40的炔基、經取代或未經取代且碳數為3至60的環烷基、經取代或未經取代且碳數為3至60的雜環烷基、經取代或未經取代且碳數為1至40的烷氧基、經取代或未經取代且碳數為6至60的芳香基、經取代或未經取代且碳數為3至60的雜芳基、經取代或未經取代且碳數為6至60的芳氧基、經取代或未經取代且碳數為1至40的矽烷基、經取代或未經取代且碳數為6至60的芳矽基、經取代或未經取代且碳數為1至40的硼烷基、經取代或未經取代且碳數為6至60的芳硼基、經取代或未經取代且碳數為1至40的膦基和經取代或未經取代且碳數為1至40的氧膦基； 式(I)中，h、i、j、k和l分別獨立為1至4的整數，即h、i、j、k和l可分別為1、2、3或4。
更佳的，該化合物表係如下式(I-I)至(I-XV)但不限於： 於式(I)中，j、k和l分別獨立為1至3的整數。
較佳的，h、i、j、k和l分別獨立為1或2，且h、i、j、k和l的總和小於或等於6。
較佳的，其中G1 可與G2 相同或相異，其中G3 可與G4 相同或相異。
較佳的，G3 至G5 可分別獨立選自於由氫原子、氘原子、鹵基、未經取代且碳數為1至12的烷基、未經取代且碳數為2至12的烯基和未經取代且碳數為2至12的炔基所構成的群組。
較佳的，所述具有至少一氮原子且碳數為3至60的雜芳基可選自於由下列所構成的群組： 其中，R1 至R7 係分別獨立選自於由下列所構成的群組：氫原子、氘原子、鹵基、氰基、硝基、三氟甲基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基、碳數為3至30的環烷基、碳數為3至30的雜環烷基、碳數為6至30的芳香基、碳數為3至20的雜芳基、碳數為1至40的烷氧基、碳數為6至30的芳氧基、碳數為1至40的矽烷基、碳數為6至30的芳矽基、碳數為1至40的硼烷基、碳數為6至30的芳硼基、碳數為1至30的膦基和碳數為1至30的氧膦基； 其中n為1至4的整數；m為1至3的整數。
較佳的，該R1 至R7 各分別獨立為，但不限於：苯基、萘基 (napthyl group)、吡啶基 (pyridine group)、嘧啶基 (pyrimidine group)、吡嗪基 (pyrazine group)、噠嗪基 (pyridazine group)、氰基、硝基、三氟甲基、氟基、聯苯基 (biphenyl group)、萘苯基 (phenylnapthyl group)、吡啶苯基 (phenylpyridine group)、嘧啶苯基 (phenylpyrimidine group)、吡嗪苯基 (phenylpyrazine group)、噠嗪苯基 (phenylpyridazine group)、氰苯基 (cyanophenyl group)、硝苯基 (nitrophenyl group)或三氟甲基苯基 (trifluoromethylphenyl group)。
較佳的，前述「具有至少一氮原子且碳數為3至60的雜芳基」可選自以下構成的群組：
其中，R1 和R2 係分別為苯基、萘基、吡啶基、嘧啶基、吡嗪基、噠嗪基、氰基、硝基、三氟甲基、氟基、聯苯基、萘苯基、吡啶苯基、嘧啶苯基、吡嗪苯基和噠嗪苯基、氰苯基、硝苯基或三氟甲基苯基。更佳的，R1 和R2 係分別為吡啶基、嘧啶基、吡嗪基、噠嗪基、氰基、硝基、三氟甲基、氟基、吡啶苯基、嘧啶苯基、吡嗪苯基和噠嗪苯基、氰苯基、硝苯基或三氟甲基苯基。於本發明中，R1 可與R2 相同或不同。
於本發明的一實施例中，G1 和/或G2 分別為主架構為吡啶基的基團，例如下述基團，但不限於：
於另一實施例，G1 和/或G2 分別為主架構為嘧啶基的基團，例如下述基團，但不限於：
於另一實施例，G1 和/或G2 分別為主架構為苯並咪唑基 (benzimidazole group)的基團，例如下述基團，但不限於：
於另一實施例，G1 和/或G2 分別為主架構為嘧啶基的基團，例如下述基團，但不限於：
於另一實施例，G1 和/或G2 分別為主架構為三嗪基(triazine group)的基團，例如下述基團，但不限於：
更佳的，前述「具有至少一氮原子且碳數為3至60的雜芳基」可以為一個經二苯基取代的三嗪基(triazine group)、經二吡啶基取代的三嗪基、經二嘧啶基取代的三嗪基、經二吡嗪基取代的三嗪基、經二噠嗪基取代的三嗪基、經二吡啶苯基取代的三嗪基、經二嘧啶苯基取代的三嗪基、經二吡嗪苯基取代的三嗪基、經二噠嗪苯基取代的三嗪基。
較佳的，該「具有至少一官能基且碳數為6至60的芳香基」係選自於由下列所構成的群組： 其中R1 是選自於由下列所構成的群組：氫原子、氘原子、鹵基、氰基、硝基、三氟甲基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基、碳數為3至30的環烷基、碳數為3至30的雜環烷基、碳數為6至30的芳香基、碳數為3至20的雜芳基、碳數為1至40的烷氧基、碳數為6至30的芳氧基、碳數為1至40的矽烷基、碳數為6至30的芳矽基、碳數為1至40的硼烷基、碳數為6至30的芳硼基、碳數為1至30的膦基和碳數為1至30的氧膦基； 其中o為0至4的整數；p為1至5的整數；o和p的總和小於或等於5。
較佳的，該新穎化合物可以為以下化合物，但並非僅限於此：
本發明另提供一有機電子裝置，其包括一第一電極、一第二電極和設置於該第一電極和該第二電極間的一有機層，該有機層包括所述化合物。
較佳的，該有機電子裝置為一有機發光二極體 (OLED)。更佳的，該新穎化合物可被使用於該電子傳輸層或電洞阻擋層。
具體而言，該有機發光二極體包括一電洞注入層、一電洞傳輸層、一發光層、一電子傳輸層和一電子注入層；該電洞注入層形成於該第一電極上；該電洞傳輸層形成於該電洞注入層上；該發光層形成於該電洞傳輸層上；該電子傳輸層形成於該發光層上，該有機層為該電子傳輸層；該電子注入層形成於該電子傳輸層和該第二電極之間。
較佳的，該電洞注入層可以為一雙層結構，即該OLED具有一第一電洞注入層和一第二電洞注入層，第一電洞注入層和第二電洞注入層設置於第一電極和電洞傳輸層之間。
相同的，該電洞傳輸層亦可以為一雙層結構，即該OLED具有一第一電洞注入層和一第二電洞注入層，第一電洞注入層和第二電洞注入層設置於電洞注入層的雙層結構與發光層之間。
較佳的，該電子傳輸層是由該新穎化合物 (如所述化合物I至CCXCIII)所製成，本發明的OLED相較於商業上的OLED具有較佳的電流效率，其中商業上的OLED使用的化合物如2-{4-[9,10-二(2-萘基)-2-蒽基]苯基}-1-苯基-1H-苯並[d]咪唑 {2-[4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl]-1-phenyl-1H-benzo[d]imidazole}、二(2-甲基-8-羥基喹啉)(p -苯基苯酚)鋁 [bis(2-methyl-8-quinolinolato)(p -phenylphenolato)aluminum]或2-(4-聯苯基)-5-(叔丁苯基)-1,3,4-惡二唑 [2-(4-biphenylyl)-5-(4-tert -butylphenyl)-1,3,4-oxadiazole)，PBD]。
較佳的，該OLED包括一電洞阻擋層，該電洞阻擋層形成於電子傳輸層和發光層之間，可防止電洞由發光層移動至電子傳輸層，所述電洞阻擋層可由前述化合物、2,9-二甲基-4,7-聯苯基-1,10-鄰二氮雜菲(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline，BCP)或2,3,5,6-四甲基-1-苯基-1,4-鄰苯二甲醯亞胺[2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide)，TMPP]所形成，但並不僅限於此。
較佳的，該OLED包括一電子阻擋層，該電子阻擋層形成於電洞傳輸層和發光層之間，可防止電子由發光層移動至電洞傳輸層，所述電子阻擋層可由4,4'-二(9-哢唑)聯苯[9,9'-(1,1'-biphenyl)-4,4'-diylbis-9H-carbazole，CBP]或4,4',4''-三(N -哢唑基)三苯胺 [4,4',4''-tri(N -carbazolyl)-triphenylamine，TCTA]所形成，但並不僅限於此。
當OLED設置有電洞阻擋層或電子阻擋層時，本發明的OLED相較於傳統的OLED具有較高的發光效率。
所述第一和第二電洞傳輸層可由N,N' -(4,4’-二聯苯基)二(N1 -(1-萘基))-N,N' -聯苯基苯-1,4-二胺 [N1 ,N1’ -(biphenyl-4,4'-diyl)bis(N1 -(naphthalen-1-yl)-N4 ,N4’ -diphenylbenzene-1,4-diamine)]或N,N' -二聯苯基-N,N' -二(1-萘基)-1,1'-聯苯-4,4'-二胺 [N4 ,N4' -di(naphthalen-1-yl)-N4 ,N4’ -diphenylbiphenyl-4,4'-diamine，NPB]所製成。
所述第一和第二電洞注入層可由聚苯胺或聚乙烯基二氧噻吩 (polyethylenedioxythiophene)所製成，但並不僅限於此。
所述發光層可由一發光材料製成，該發光材料包括一主發光體 (host)和一摻雜物 (dopant)，其中主發光體的材料例如9-[4-(1-萘基)苯基]-10-(2-萘基)蒽 [9-(4-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl)anthracene]，但不限於此。
針對紅光OLED，發光層中的摻雜物可以為具有苝 (perylene)配位基、熒蒽 (fluoranthene)配位基或二茚並 (periflanthene)配位基的二價銥有機金屬化合物，但並不僅限於此。針對綠光OLED，發光層中的摻雜物可以為二氨基芴 (diaminoflourenes)、蒽二胺 (diaminoanthracenes)或具有苯基吡啶 (phenylpyridine)配位基的二價銥有機金屬化合物，但並不僅限於此。針對藍光OLED，發光層中的摻雜物可以為二氨基芴、蒽二胺、芘二胺 (diaminopyrenes)或具有苯基吡啶配位基的二價銥有機金屬化合物，但並不僅限於此。藉由不同的主發光體材料，OLED可產生紅光、綠光或藍光的光線。
所述電子注入層可以一電子注入材料製成，例如8-氧代萘-1-基鋰 [(8-oxidonaphthalen-1-yl)lithium(II)]，但不限於此。
所述第一電極可以為氧化銦錫電極 (indium-doped tin oxide electrode)，但並不僅限於此。
所述第二電極的功函數 (work function)低於第一電極的功函數。因此，第二電極可以是但不侷限於鋁電極、銦電極或鎂電極。
本發明的其他目的、功效和技術特徵，會以圖式、實施例和比較例進行更詳細的說明。
以下列舉數種實施例作為例示說明本發明的化合物及其有機電子裝置的實施方式，以突顯本發明相較於現有技術的差異；熟習此技藝者可經由本說明書的內容輕易了解本發明所能達成的優點與功效，並且於不悖離本發明之精神下進行各種修飾與變更，以施行或應用本發明的內容。
中間物 A1 的合成
中間物A1 (Intermediate A1)係用於製備一種新穎化合物，中間物A1可藉由下述合成機制A1中的步驟進行合成。合成機制A1
步驟1：合成中間物A1-1
混合86克 (1.0當量)的3-溴二苯並[a,d]環庚烯-5-酮 (3-bromodibenzo[a,d]cyclohepten-5-one)、106克 (2.0當量)的N -溴代丁二醯亞胺(N -bromosuccinimide，NBS)和0.7克 (0.01當量)的過氧化苯甲醯 (benzyl peroxide)於430毫升的四氯化碳 (carbon tetrachloride，CCl4 )中，並加熱至85°C進行反應，在反應的過程中以高效液相層析儀 (high performance liquid chromatography，HPLC)進行監測；當反應完成後，過濾分離反應產生的沉澱物，並以甲醇沖洗再以再結晶的方式純化，接著經濃縮和乾燥後，獲得123克的白色固體產物，產率為92.3%。
經場脫附質譜 (field desorption mass spectroscopy，FD-MS)分析確定，白色固體產物即為中間物A1-1。FD-MS分析結果：C15 H9 Br3 O，理論值444.94，檢測值444.94。
步驟2：合成中間物A1-2
秤取116.0克 (1.0當量)的中間物A1-1，使中間物A1-1溶解於960毫升呋喃 (furan)和四氫呋喃 (tetrahydrofuran，THF)體積比為2：1的混合溶液中，並降溫至0°C，加入87.8克 (3.0當量)的叔丁醇鉀 (potassiumtert -butoxide，KO-t -Bu)後於0°C下攪拌1小時，另接續於室溫下攪拌12小時。在反應進行後，以去離子水急速冷卻並以溶劑萃取獲得有機層，再以硫酸鈉達到除水的目的，接著透過減壓蒸餾法去除有機層中的溶劑，並以矽膠管柱層析純化獲得純化產物，純化產物經濃縮和乾燥後可獲得46.8克的淡黃色固體產物，產率為51.1%。
經FD-MS分析確定，淡黃色固體產物即為中間物A1-2。FD-MS分析結果：C19 H11 BrO2 ，理論值351.19，檢測值為351.19。
步驟3：合成中間物A1-3
將53.5克 (1.0當量)的中間物A1-2懸浮液和8.1克 (0.025當量)5%的鈀碳催化劑(palladium on carbon，Pd/C)於535毫升的乙酸乙酯 (ethyl acetate，EA)中混合，並在氫氣氣球提供的氫氣環境下攪拌3至6小時；接著，反應後的混合產物以矽藻土層過濾並以EA洗淨，並使濾液在減壓環境下進行濃縮，最後獲得100克的黃色固體產物，產率為100%。
經FD-MS分析確定，黃色固體產物即為中間物A1-3。FD-MS分析結果：C19 H13 BrO2 ，理論值為353.21，檢測值為353.21，中間物A1-3不需進一步純化即可直接使用於接下來的步驟。
步驟4：合成中間物A1-4
53克 (1.0當量)的中間物A1-3和57克 (2.0當量)的對甲苯磺酸 (p -toluenesulfonic acid，PTSA)在530毫升的甲苯中加熱迴流12小時，形成反應混合液；待反應混合液降至室溫後，以碳酸氫鈉飽和水溶液急速冷卻反應混合液，再以二氯甲烷萃取獲得有機層，並水洗有機層、使有機層浸泡於無水硫酸鈉中乾燥獲得產物溶液，產物溶液以減壓濃縮，並以二氯甲烷和己烷體積比為1：1的洗提液於矽膠管柱中層析純化，最後獲得淡黃色固體產物，產率為91.5%。
經FD-MS分析確定，淡黃色固體產物即為中間物A1-4。FD-MS分析結果：C19 H11 BrO，理論值335.19，檢測值為335.19。
中間物 A2 的合成
中間物A2係用於製備一種新穎化合物，中間物A2是以類似於合成中間物A1的步驟1至步驟4所合成，其差異在於起始物3-溴二苯並[a,d]環庚烯-5-酮以2-溴二苯並[a,d]環庚烯-5-酮 (CAS No. 198707-82-3)代替，中間物A2的合成路徑統整於合成機制A2中，在合成機制A2中所有中間物的分析方法皆同前述，分析結果列於下表1。合成機制A2
中間物 A3 的合成
中間物A3係用於製備一種新穎化合物，中間物A3是以類似於合成中間物A1的步驟1至步驟4所合成，其差異在於起始物3-溴二苯並[a,d]環庚烯-5-酮以3,7-二溴二苯並[a,d]環庚烯-5-酮 (3,7-dibromodibenzo[a,d]cyclohepten-5-one) (CAS No. 226946-20-9)代替，中間物A3的合成路徑統整於合成機制A3中，在合成機制A3中所有中間物的分析方法皆同前述，分析結果列於下表1。合成機制A3 表1：各中間物的化學結構式、產率、分子式與以FD-MS分析所得質量。
中間物 A1 至 A3 的修飾
除了中間物A1至A3之外，所屬技術領域具有通常知識者可更替合成機制A1至A3中的起始物，並以類似於合成機制A1至A3的合成路徑合成出其他中間物，例如以下列出的中間物A4至A15：
中間物 B1 的合成
前述中間物A1進一步與2-溴聯苯 (2-bromo-biphenyl)反應，以合成出中間物B1，該中間物B1的合成路徑係如合成機制B1所示。合成機制B1
步驟1：合成中間物B1-1
1.0當量的2-溴聯苯溶解於120毫升的無水THF，並降溫至-78°C，再將2.5 M (1.0當量)的正丁基鋰 (n -butyl lithium，n -BuLi)緩慢加入前述低溫溶液中並攪拌1小時後形成反應溶液。接著，將0.7當量的中間物A1加入反應溶液中在室溫下攪拌3小時，反應完成後，以飽和氯化銨水溶液冷卻，再以有機溶劑萃取出有機層，並將有機層分離、濃縮並以石油醚 (petroleum ether)使之再結晶，最後可得白色固體產物，產率為83.1%。
經FD-MS分析確定，白色固體產物即為中間物B1-1。FD-MS分析結果：C31 H21 BrO，理論值489.40，檢測值為489.40。
步驟2：合成中間物B1
將1.0當量的中間物B1-1、體積為中間物B1-1質量3倍的醋酸(即w/v=1/3)和5滴的硫酸於110°C下攪拌混合6小時。然後減壓蒸發去除溶劑，並以管柱層析純化殘留物，接著以甲苯依序進行濃縮和再結晶的步驟，最後可得白色固體產物，產率為93.0%。
經FD-MS分析確定，白色固體產物即為中間物B1。FD-MS分析結果：C31 H19 Br，理論值471.39，檢測值為471.39。
中間物 B2 的合成
中間物B2是以類似於合成中間物B1的步驟1和步驟2所合成，其差異在於將步驟1中的中間物A1以中間物A2代替，中間物B2的合成路徑統整於合成機制B2中。本實驗係以如前述相同的分析方法分析合成機制B2中所得之所有中間物，分析結果列於下表2。合成機制B2
中間物 B3 的合成
中間物B3是以類似於合成中間物B1的步驟1和步驟2所合成，其差異在於將步驟1中的中間物A1以中間物A3代替，中間物B3的合成路徑統整於合成機制B3中。本實驗係以如前述相同的分析方法分析合成機制B3中所得之所有中間物的，分析結果列於下表2。合成機制B3 表2：各中間物的化學結構式、產率、分子式與以FD-MS分析所得質量。
中間物 B1 至 B3 的修飾
除了中間物B1至B3之外，所屬技術領域具有通常知識者可自中間物A1至A15中選擇，作為更替合成機制B1至B3中的起始物，並以類似於合成機制B1至B3的合成路徑合成出其他中間物，例如下述的中間物B4至B15：
中間物 C1 的合成
前述中間物B1可進一步與聯硼酸頻那醇酯 [bis(pinacolato)diboron]反應合成中間物C1，中間物C1可藉由下述合成機制C1合成。合成機制C1
混合1.0 當量的中間物B1、1.2當量的聯硼酸頻那醇酯、0.0025當量的 [1,1-雙(二苯基膦基)二茂鐵]二氯化鈀 [1,1-bis(diphenylphosphino)-ferrocene dichloropalladium(II)，PdCl2 (dppf)2 ]和3.0當量的醋酸鉀於0.3 M的1,4-二噁烷 (1,4-dioxane)中，加熱至100°C的並在氮氣環境下攪拌8小時，冷卻於室溫後減壓去除溶劑，並以管柱層析儀純化殘留液而可獲得白色固體產物，產率95.7%。
經由FD-MS分析確定，白色固體產物即為中間物C1。FD-MS分析結果：C37 H31 BO2 ，理論值518.45，檢測值為518.45。
中間物 C2 的合成 中間物C2是以類似於中間物C1的方式所合成，其差異在於：該中間物B1是以中間物B2代替，中間物C2可藉由下述合成機制C2合成，產率為96.1%。
經由FD-MS分析確定，獲得的固體產物即為中間物C2。FD-MS分析結果：C37 H31 BO2 ，理論值518.45，檢測值為518.45。合成機制C2
中間物 C3 的合成
中間物C3是以類似於中間物C1的方式所合成，其差異在於：該中間物B1是以中間物B3代替，且聯硼酸頻那醇酯的使用當量增加為2.4當量。具體而言，中間物C3可藉由下述合成機制C3合成，產率為84.2%。 經由FD-MS分析確定，獲得的固體產物即為中間物C3。FD-MS分析結果：C43 H42 B2 O4 ，理論值644.41，檢測值為644.40。合成機制C3
新穎化合物 I 至 XIV 的合成
方法1：
中間物B1至B3皆可被用於合成新穎化合物，合成路徑統整於合成機制I中，其中，「中間物B」係選自於包括中間物B1至B3的群組，「反應物A (Reactant A)」係選自於下表3中包括反應物A1至A6的群組。合成機制I 表3：各反應物A1至A6的化學結構式與CAS編號。
方法2：
中間物C1至C3可分別與各反應物合成出各種本發明所保護的新穎化合物，該新穎化合物可藉由下述合成機制II所合成。其中，「中間物C」可以選自由中間物C1至C3所構成的群組；「反應物B」可以選自由表3-2中反應物B1至B5所構成的群組。合成機制II 表3-2：各反應物B1至B5的的化學結構式與CAS編號。
具體而言，將1.2當量的反應物A、1.0當量的中間物B或C、0.005當量的三(二亞苄基丙酮)二鈀 [tris(dibenzylideneacetone)dipalladium(0)，Pd2 (dba)3 ]、0.5%當量的乙酸鈀 [palladium acetate，Pd(OAc)2 ]、0.02當量的(SPhos)、0.5 M甲苯和乙醇體積比為10：1的溶液中和3.0 M的碳酸鉀水溶液置於500毫升的茄形瓶中，在100°C通有氮氣的環境下攪拌12小時；於此步驟中，可藉由改變反應物A或反應物B以及催化劑的使用當量數，會依位置選擇性 (regioselectivity)合成出單一或偶聯的產物。反應完成後，於茄形瓶中加入水和甲苯使反應溶液分層，接著，將萃取出的有機層以硫酸鈉乾燥，並以減壓蒸餾去除有機層中的溶劑，再將殘留物以矽膠管柱層析純化，並以甲苯進行濃縮和再結晶的步驟，最後可得白色固體產物，即為本發明的新穎化合物。
前述各種反應物和中間物可用以合成化合物I至化合物XIV並列於表4，化合物I至化合物XIV可以氫核磁共振(1 H nuclear magnetic resonance，1 H-NMR)和FD-MS分析確定，並且，化合物I至化合物XIV的化學結構式、產率、分子式和以FD-MS分析所得質量亦列於表4中。根據圖2至圖15以及表4的質量資訊，化合物I至化合物XIV的化學結構式確認如下。 表4：合成各化合物I至化合物XIV使用的反應物、中間物、產率、分子式與以FD-MS分析所得質量。
化合物 I 至化合物 XIV 的修飾
除了前述化合物I至化合物XIV之外，所屬技術領域具有通常知識者可選用其他反應物和中間物B1至B3或中間物C1至C3，並以類似於合成機制I或II的合成路徑合成出本發明所請之各種新穎化合物。
OLED 裝置的製備
將塗佈有1500 Å厚ITO層的玻璃基板 (以下簡稱為ITO基板)置於含有洗潔劑 (廠牌：Fischer Co.)的蒸餾水 (以Millipore Co.公司的濾器過濾二次而得的蒸餾水)中，並以超音波震盪30分鐘；更換蒸餾水後再以超音波震盪10分鐘以洗淨ITO基板，並重複上述洗淨步驟一次；洗淨後，將前述玻璃基板以異丙醇、丙酮和甲醇以超音波震盪洗淨，並使之乾燥；接著，將玻璃基板置於電漿表面清潔機內，並以氧電漿清潔玻璃基板5分鐘，再將清潔後的玻璃基板置於真空蒸鍍機內。
之後，將真空蒸鍍機的真空度維持在1x10-6 torr至3x10-7 torr，並於ITO基板上依序沉積各種有機材料和金屬材料，並獲得上述實施例和比較例的OLED裝置。於此，該ITO基板上係依序沉積有第一電洞注入層 (HIL-1)、第二電洞注入層 (HIL-2)、第一電洞傳輸層 (HTL-1)、第二電洞傳輸層 (HTL-2)、藍/綠/紅發光層 (BEL/GEL/REL)、電子傳輸層 (ETL)、電子注入層 (EIL)和陰極 (Cthd)。
在上述OLED裝置的各層中，HAT是用於形成HIL-1和HID；HI-2是用於形成HIL-2；HT-1和HT-2是用於形成HTL-1和HTL-2；傳統的ET和本發明的新穎化合物是用於形成ETL；Liq是用於形成ETD和EIL；RH/GH/BH分別為形成REL/GEL/BEL的主要材料；RD/GD/BD-1/BD-2可作為REL/GEL/BEL的摻雜物。實施例的OLED裝置和比較例的OLED裝置的主要差異為：比較例的OLED裝置中ETL是以BCP製成，實施例的OELD裝置中ETL是以列於表4的新穎化合物所製成。上述各化合物的詳細化學結構式列於表5。 表5：使用於OLED裝置中商業材料的化學結構式。
紅光 OLED 裝置的製備
紅光OLED裝置包括複數有機層，各有機層依序沉積於ITO基板上，各有機層的材料和厚度分別列於表6中。 表6：紅光OLED裝置中各有機層的塗佈順序、名稱、材料和厚度。
綠光 OLED 裝置的製備
綠光OLED裝置包括複數有機層，該等有機層依序沉積於ITO基板上，各有機層的材料和厚度分別列於表7中。 表7：綠光OLED裝置中各有機層的塗佈順序、名稱、材料和厚度。
藍光 OLED 裝置的製備
藍光OLED裝置包括複數有機層，該等有機層依序沉積於ITO基板上，各有機層的材料和厚度分別列於表8中。
針對藍光OLED裝置，發光層摻雜物可以是表5中的BD-1或BD-2，實施例B-4至B-8以及比較例B-1的OLED裝置中所選用的摻雜物是BD-1；實施例B-1至B-3以及比較例B-2的OLED裝置中所選用的摻雜物是BD-2。 表8：藍光OLED裝置中各有機層的塗佈順序、名稱、材料和厚度。
OLED 裝置的效能
為了評估OLED裝置的效能，分別將紅光、綠光和藍光OLED裝置連接於電源供應器 (廠牌：Keithley；型號：2400)，並以PR650的光度計檢測，所測得之色度以為國際照明委員會 (Commission Internationale de L’Eclairage 1931，CIE)制定的色度座標[color coordinate (x,y)]示之，檢測結果列於下表9中。其中，藍光和紅光的OLED裝置是在1000尼特 (1 nit=1 cd/m2 )的亮度下檢測；綠光的OLED裝置是在3000尼特的亮度下檢測。
實施例R-1至R-4和比較例R中OLED裝置的ETL材料、顏色、CIE、驅動電壓和電流效率列於下表9中。實施例G-1至G-5以及比較例G中OLED裝置的ETL材料、顏色、CIE、驅動電壓和電流效率列於下表10中。實施例B-1至B-8以及比較例B-1和B-2中OLED裝置的ETL材料、顏色、CIE、驅動電壓和電流效率列於下表11中。 表9：實施例R-1至R-4和比較例R中OLED裝置的ETL材料、顏色、CIE、驅動電壓和電流效率。 表10：實施例G-1至G-5和比較例G中OLED裝置的ETL材料、顏色、CIE、驅動電壓和電流效率。 表11：實施例B-1至B-8和比較例B-1和B-2中OLED裝置的ETL材料、顏色、CIE、驅動電壓和電流效率。
根據實驗結果可知，相較於市面上電子傳輸層材料(BCP)，選用本發明之新穎化合物作為電子傳輸材料可降低紅光、綠光或藍光OLED裝置的驅動電壓並提升電流效率。實驗結果證實本發明的新穎化合物確實能適用添加於各色OLED裝置中，並可達到降低驅動電壓和提升電流效率的功效。
上述實施例僅係為說明本創作之例示，並非於任何方面限制本創作所主張之權利範圍，所屬技術領域中具有通常知識者能根據本創作之精神針對例如取代基的數量、位置或排列加以調整。本創作所主張之權利範圍自應以申請專利範圍所述為準，而非僅限於上述具體實施例。
11‧‧‧基板 12‧‧‧陽極 13‧‧‧電洞注入層 14‧‧‧電洞傳輸層 15‧‧‧發光層 16‧‧‧電子傳輸層 17‧‧‧電子注入層 18‧‧‧陰極
圖1為OLED的側視剖面圖。 圖2至圖15分別為化合物I至化合物XIV的氫核磁共振光譜圖。
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Claims (16)

  1. 一種化合物，其係如下式(I)所示： G1 至G4 中其中之一者是選自於由下列所構成的群組：具有至少一氮原子且碳數為3至60的雜芳基、具有至少一官能基且碳數為1至40的烷基、具有至少一官能基且碳數為2至40的烯基、具有至少一官能基且碳數為2至40的炔基、具有至少一官能基且碳數為3至60的環烷基、具有至少一官能基且碳數為3至60的雜環烷基、具有至少一官能基且碳數為1至40的烷氧基、具有至少一官能基且碳數為6至60的芳香基、具有至少一官能基且碳數為6至60的芳氧基、具有至少一官能基且碳數為1至40的矽烷基、具有至少一官能基且碳數為6至60的芳矽基、具有至少一官能基且碳數為1至40的硼烷基、具有至少一官能基且碳數為6至60的芳硼基、具有至少一官能基且碳數為1至40的膦基和具有至少一官能基且碳數為1至40的氧膦基； 該官能基係選自於由氰基、硝基、三氟甲基、氟基和氯基所構成的群組； G1 至G4 中其他者以及G5 係分別獨立選自於由下列所構成的群組：氫原子、氘原子、鹵基、氰基、硝基、三氟甲基、經取代或未經取代且碳數為1至40的烷基、經取代或未經取代且碳數為2至40的烯基、經取代或未經取代且碳數為2至40的炔基、經取代或未經取代且碳數為3至60的環烷基、經取代或未經取代且碳數為3至60的雜環烷基、經取代或未經取代且碳數為1至40的烷氧基、經取代或未經取代且碳數為6至60的芳香基、經取代或未經取代且碳數為3至60的雜芳基、經取代或未經取代且碳數為6至60的芳氧基、經取代或未經取代且碳數為1至40的矽烷基、經取代或未經取代且碳數為6至60的芳矽基、經取代或未經取代且碳數為1至40的硼烷基、經取代或未經取代且碳數為6至60的芳硼基、經取代或未經取代且碳數為1至40的膦基和經取代或未經取代且碳數為1至40的氧膦基； 其中，h、i、j、k和l分別獨立為1至4的整數。
  2. 如請求項1所述之化合物，其中h、i、j、k和l分別獨立為1至2的整數，且h、i、j、k和l的總和小於或等於6。
  3. 如請求項1所述之化合物，其中該化合物表係如下式(I-I)至(I-XV)所示： 其中j、k和l分別獨立為1至3的整數。
  4. 如請求項1所述之化合物，其中該具有至少一氮原子且碳數為3至60的雜芳基是選自於由下列所構成的群組： 其中，R1 至R7 係分別獨立選自於由下列所構成的群組：氫原子、氘原子、鹵基、氰基、硝基、三氟甲基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基、碳數為3至30的環烷基、碳數為3至30的雜環烷基、碳數為6至30的芳香基、碳數為3至20的雜芳基、碳數為1至40的烷氧基、碳數為6至30的芳氧基、碳數為1至40的矽烷基、碳數為6至30的芳矽基、碳數為1至40的硼烷基、碳數為6至30的芳硼基、碳數為1至30的膦基和碳數為1至30的氧膦基； 其中n為1至4的整數；m為1至3的整數。
  5. 如請求項1所述之化合物，其中該具有至少一氮原子且碳數為3至60的雜芳基係選自於由下列所構成的群組： 其中，R1 和R2 係分別獨立選自於由下列所構成的群組：苯基、萘基、吡啶基、嘧啶基、吡嗪基、噠嗪基、氰基、硝基、三氟甲基、氟基、聯苯基、萘苯基、吡啶苯基、嘧啶苯基、吡嗪苯基、噠嗪苯基、氰苯基、硝苯基、三氟甲基和苯基。
  6. 如請求項5所述之化合物，其中該R1 和R2 係分別獨立選自於由下列所構成的群組：吡啶基、嘧啶基、吡嗪基、噠嗪基、氰基、硝基、三氟甲基、氟基、吡啶苯基、嘧啶苯基、吡嗪苯基和噠嗪苯基、氰苯基、硝苯基和三氟甲基苯基。
  7. 如請求項1所述之化合物，其中該具有至少一氮原子且碳數為3至60的雜芳基係選自於由下列所構成的群組：
  8. 如請求項1所述之化合物，其中該具有至少一官能基且碳數為6至60的芳香基係選自於由下列所構成的群組： 其中R1是選自於由下列所構成的群組：氫原子、氘原子、鹵基、氰基、硝基、三氟甲基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基、碳數為3至30的環烷基、碳數為3至30的雜環烷基、碳數為6至30的芳香基、碳數為3至20的雜芳基、碳數為1至40的烷氧基、碳數為6至30的芳氧基、碳數為1至40的矽烷基、碳數為6至30的芳矽基、碳數為1至40的硼烷基、碳數為6至30的芳硼基、碳數為1至30的膦基和碳數為1至30的氧膦基； 其中o為0至4的整數；p為1至5的整數；o和p的總和小於或等於5。
  9. 如請求項1所述之化合物，其中G3 至G5 是分別獨立選自於由氫原子、氘原子、鹵基、未經取代且碳數為1至12的烷基、未經取代且碳數為2至12的烯基和未經取代且碳數為2至12的炔基所構成的群組。
  10. 如請求項1所述之化合物，其中G1 和G2 相同。
  11. 如請求項1所述之化合物，其中G3 和G4 相同。
  12. 如請求項1所述之化合物，其中該化合物係選自於由下列所構成的群組：
  13. 一種有機電子裝置，其包括一第一電極、一第二電極和設置於該第一電極和該第二電極間的一有機層，其中該有機層包括如請求項1至12中任一項所述的化合物。
  14. 如請求項13所述的有機電子裝置，其中該有機電子裝置為一有機發光二極體。
  15. 如請求項14所述的有機電子裝置，其中該有機發光二極體包括： 一電洞注入層，其形成於該第一電極上； 一電洞傳輸層，其形成於該電洞注入層上； 一發光層，其形成於該電洞傳輸層上； 一電子傳輸層，其形成於該發光層上，該有機層為該電子傳輸層；和 一電子注入層，其形成於該電子傳輸層和該第二電極之間。
  16. 如請求項14所述的有機電子裝置，其中該有機發光二極體包括： 一電洞注入層，其形成於該第一電極上； 一電洞傳輸層，其形成於該電洞注入層上； 一發光層，其形成於該電洞傳輸層上； 一電洞阻擋層，其形成於該發光層上，該有機層為該電洞阻擋層； 一電子傳輸層，其形成於該電洞阻擋層上；和 一電子注入層，其形成於該電子傳輸層和該第二電極之間。
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