TWI653218B - 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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TWI653218B
TWI653218B TW106141975A TW106141975A TWI653218B TW I653218 B TWI653218 B TW I653218B TW 106141975 A TW106141975 A TW 106141975A TW 106141975 A TW106141975 A TW 106141975A TW I653218 B TWI653218 B TW I653218B
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carbons
carbon atoms
ring
groups
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TW106141975A
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TW201821401A (zh
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吳蕙玲
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

本發明提供一種化合物及其有機電子裝置，化合物如下式(I)所示：； 其中X1 和X2 分別獨立為C(Ra )，該二(Ra )彼此相同或不同，該二(Ra )相互連接形成一第一芳香環；X3 和X4 分別獨立為C(Rb )，該二(Rb )彼此相同或不同，該二(Rb )相互連接形成一第二芳香環，該第二芳香環為一多環芳香環。

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 VanSlyke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]聯吡啶 {(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係如下式(I)所示： 式(I)中，X1 和X2 分別獨立為C(Ra )，該二(Ra )彼此相同或不同，該二(Ra )相互連接形成一第一芳香環； 式(I)中，X3 和X4 分別獨立為C(Rb )，該二(Rb )彼此相同或不同，該二(Rb )相互連接形成一第二芳香環，該第二芳香環為一多環芳香環； 式(I)中，Z1 至Z12 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、碳數為1至40的烷基、碳數為2至40的烯基、碳數為2至40的炔基、碳數為3至60的環烷基、碳數為3至60的雜環烷基、碳數為6至60的芳香基、碳數為3至60的雜芳基、碳數為1至40的烷氧基、碳數為6至60的芳氧基、碳數為1至40的矽烷基 (alkylsilyl group)、碳數為6至60的芳矽基 (arylsilyl group)、碳數為1至40的硼烷基 (alkylboron group)、碳數為6至60的芳硼基 (alkylboron group)、碳數為1至40的膦基 (phosphine group)和碳數為1至40的氧膦基 (phosphine oxide group)。
根據本發明，式(I)中由X3 和X4 延伸形成的該多環芳香環包含至少二相互連接並合的芳香環，該多環芳香環中的該至少二芳香環之環上的原子為碳原子，不包含如氮、氧或硫的原子，即該至少二芳香環不會是雜芳環，但該芳香環可連接有任何取代基，且該取代基可包含除了碳以外的其他原子。
根據本發明，式(I)中X1 和X2 間的雙鍵以及該二(Ra )間的鍵共軛形成該第一芳香環。相似的，式(I)中由X3 和X4 間的雙鍵以及該二(Rb )間的鍵共軛形成該多環芳香環。根據本發明，由X1 和X2 延伸形成的第一芳香環和由X3 和X4 延伸形成的多環芳香環相互連接並合成一芳香基，該芳香基具有至少六個共軛的雙鍵，較佳的，該芳香基具有至少八個共軛的雙鍵。
由X3 和X4 延伸形成的多環芳香環可以為但不限：一經取代或未經取代的萘環(naphthalene ring)、一經取代或未經取代的蒽環(anthracene ring)、一經取代或未經取代的菲環(phenanthrene ring)、一經取代或未經取代的芴環(fluorene ring)、一經取代或未經取代的芘環(pyrene ring)、一經取代或未經取代的苯並菲環(benzophenanthrene ring)、一經取代或未經取代的苯並芘環(benzopyrene ring)、一經取代或未經取代的熒蒽環(fluoranthene ring)、一經取代或未經取代的苯並熒蒽環(benzofluoranthene ring)或一經取代或未經取代的三亞苯環(triphenylene ring)。前述多環芳香環可取代有至少一氘原子、至少一碳數為1至12的烷基、至少一碳數為2至12的烯基、至少一碳數為2至12的炔基或至少一碳數為6至12的芳香基。例如，該經取代的芴環可取代有一甲烷基、二甲烷基或二苯基，即，該經取代的芴環為9-二甲基芴環(9-methylfluorene ring)、9,9-二甲基芴環(9,9-dimethylfluorene ring)或9,9-二苯基芴環(9,9-diphenylfluorene ring)。
較佳的，Z1 至Z12 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、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30的雜芳基、碳數為1至12的烷氧基、碳數為6至30的芳氧基、碳數為1至12的矽烷基、碳數為6至30的芳矽基、碳數為1至12的硼烷基、碳數為6至30的芳硼基、碳數為1至12的膦基和碳數為1至12的氧膦基。
舉例而言，該化合物可下式(I-I)至(I-XII)中任一表示：
於上述式(I-I)至(I-XII)中，n1為0至4的正整數，T可以是但不限於：氫原子、氘原子、甲基、乙基、丙基、丁基、戊基、己基或苯基。
較佳的，所述任一通式中自X1 和X2 延伸形成的該第一芳香環為一經取代或未經取代且碳數為6至60的碳環，更佳的，自X1 和X2 延伸形成的該第一芳香環為一經取代或未經取代且碳數為6至20的碳環。例如，該經取代或未經取代且碳數為6至60的碳環可以選自於由下列所構成的群組：一經取代或未經取代的苯環結構、一經取代或未經取代的萘環結構、一經取代或未經取代的蒽環結構、一經取代或未經取代的菲環結構、一經取代或未經取代的芘環結構、一經取代或未經取代的苯並菲環結構、一經取代或未經取代的苯並芘環結構、一經取代或未經取代的熒蒽環結構、一經取代和未經取代的苯並熒蒽環結構和一經取代或未經取代的芴環結構，但不限於此。更佳的，該經取代或未經取代且碳數為6至60的碳環為一經取代或未經取代的苯環結構。該碳數為6至60的碳環上的取代基可以是但不限於氘原子、鹵基、氰基、硝基、碳數為1至12的烷基、碳數為2至12的烯基或碳數為2至12的炔基。
較佳的，所述任一通式中Z1 至Z8 中的至少一者是獨立選自於由下列所構成的群組：碳數為1至40且具有至少一官能基的烷基、碳數為2至40且具有至少一官能基的烯基、碳數為2至40且具有至少一官能基的炔基、碳數為3至60且具有至少一官能基的環烷基、碳數為3至60且具有至少一官能基的雜環烷基、碳數為6至60且具有至少一官能基的芳香基、碳數為1至40且具有至少一官能基的烷氧基、碳數為6至60且具有至少一官能基的芳氧基、碳數為1至40且具有至少一官能基的矽烷基、碳數為6至60且具有至少一官能基的芳矽基、碳數為1至40且具有至少一官能基的硼烷基、碳數為6至60且具有至少一官能基的芳硼基、碳數為1至40且具有至少一官能基的膦基和碳數為1至40且具有至少一官能基的氧膦基；而所述任一通式中Z1 至Z8 中的其他者可以是氫原子、氘原子或說明書中提到的其餘取代基。所述官能基可選自於由氰基、硝基、三氟甲基、氟基和氯基所構成的群組。
詳細來說，所述任一通式中Z1 至Z8 中的至少一者係一特定芳香取代基，該特定芳香取代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、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0至4的正整數；m為0至3的正整數；o是0至3的正整數；m和o的總和小於或等於5。
較佳的，R1 至R3 各自獨立為但不限於苯基、吡啶基、嘧啶基、吡嗪基、噠嗪基、苯並吡啶基、苯並嘧啶基、苯並吡嗪基或苯並噠嗪基。
於其中一實施例，所述任一通式中Z1 至Z8 中至少一者為，其中，R1 可以是吡啶基或苯氰基(cyanophenyl)，且R2 和R3 可以是上述之任一取代基。
於另一實施例，所述任一通式中Z1 至Z8 中至少一者為，其中，R2 可以是吡啶基或苯氰基(cyanophenyl)，且R1 和R3 可以是上述之任一取代基。
較佳的，所述任一通式中Z1 、Z2 、Z3 、Z6 、Z7 和Z8 中至少一者是一經二苯基、二吡啶基、二嘧啶基、二吡嗪基、二噠嗪基、二苯並吡啶基、二苯並嘧啶基、二苯並吡嗪基或二苯並噠嗪基取代的三嗪基(triazine group)。
較佳的，所述任一通式中Z1 、Z2 、Z3 、Z6 、Z7 和Z8 中至少一者是選自於上述特定芳香取代基，而Z4 和Z5 各自獨立選自於由氫原子、氘原子、鹵基、氰基、硝基、碳數為1至12的烷基、碳數為2至12的烯基和碳數為2至12的炔基所構成的群組。
較佳的，所述任一通式中Z2 、Z3 、Z6 和Z7 中至少一者是選自於由下列所構成的群組：
較佳的，所述任一通式中的Z9 至Z12 可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、碳數為1至12的烷基、碳數為2至12的烯基和碳數為2至12的炔基。
根據本發明，所述任一通式中的Z1 和Z8 可以是相同或是不同，Z2 和Z7 可以是相同或是不同，Z3 和Z6 可以是相同或是不同；於其中一實施例，Z1 、Z2 、Z3 、Z6 、Z7 和Z8 中的任其中二者可以是上述相同的取代基，而Z1 、Z2 、Z3 、Z6 、Z7 和Z8 中其他者可以選自於由下列所構成的群組：氫原子、氘原子、鹵基、氰基、硝基、碳數為1至12的烷基、碳數為2至12的烯基和碳數為2至12的炔基。
例如，Z1 、Z4 至Z8 各自獨立為氫原子或氘原子，Z2 和/或Z3 可以是該特定的芳香取代基；或者，Z1 、Z2 、Z4 、Z5 、Z7 和Z8 各自獨立為氫原子或氘原子，且Z3 和Z6 皆為上述特定的芳香取代基。
舉例而言，化合物可以選自於由下列所構成的群組：
本發明提供了一種有機電子裝置，該有機電子裝置包括一第一電極、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，該有機層具有前述化合物。
較佳的，該有機電子裝置為一有機發光二極體。更佳的，本發明的新穎化合物可被用於形成電子傳輸層或電洞阻擋層的材料。
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；該電子注入層形成於該電子傳輸層和該第二電極之間。
於其中一實施例，該有機層可以為電子傳輸層，即該電子傳輸層包含前述的新穎化合物。
較佳的，該電洞注入層可以為一雙層結構，即該OLED於第一電極和電洞傳輸層之間具有一第一電洞注入層和一第二電洞注入層。
較佳的，該電洞傳輸層亦可以為一雙層結構，即該OLED於電洞注入層的雙層結構與發光層之間具有一第一電洞傳輸層和一第二電洞傳輸層。
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CXXXVIII)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OLED中使用的已知電子傳輸層材料如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-(4-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所述化合物、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，但不限於上述。於另一實施例，該有機層可以為電洞阻擋層，該電洞阻擋層具有前述新穎化合物。
較佳的，該OLED包括一形成於電洞傳輸層和發光層之間的電子阻擋層，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9,9’-(1,1’-聯苯基)-4,4’-二基二-9H-咔唑[9,9'-(1,1'-biphenyl)-4,4'-diylbis-9H-carbazole，CBP]或4,4',4''-三(N -咔唑基)三苯胺 [4,4',4''-tri(N -carbazolyl)-triphenylamine，TCTA]所形成，但不限於上述。
當OLED設置有電洞阻擋層或電子阻擋層於時，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' -(聯苯-4,4’-二基)二(N1 -(1-萘基))-N4 ,N4' -二苯基苯-1,4-二胺 [N1 ,N1’ -(biphenyl-4,4'-diyl)bis(N1 -(naphthalen-1-yl)-N4 ,N4’ -diphenylbenzene-1,4-diamine)]或N4 ,N4' -二(萘-1-基)-N4 ,N4’ -二苯聯苯基-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 (polyaniline)或聚乙烯基二氧噻吩 (polyethylenedioxythiophene)所製成，但不限於上述。
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 (dopant)可以為具有苝配位基(perylene ligands)、熒蒽配位基 (fluoranthene ligands)或二茚並配位基 (periflanthene ligands)的二價銥有機金屬化合物，但不限於此。針對綠光OLED，發光層中的摻雜物可以為二氨基芴 (diaminofluorenes)、蒽二胺 (diaminoanthracenes)或具有苯基吡啶配位基 (phenylpyridine ligands)的二價銥有機金屬化合物，但不限於此。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，但不限於此。藉由不同的主發光體材料，OLED可發出紅光、綠光或藍光。
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)，但不限於上述。
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)於起始材料5倍體積的四氯化碳 (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，降溫至0°C，再加入87.8克 (3.0當量)的叔丁醇鉀 (potassiumtert -butoxide，K-Ot Bu)後於0°C下攪拌1小時，另接續於室溫下再攪拌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 g、1.0當量的中間物A1-3和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，在減壓環境下濃縮產物溶液，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46克的淡黃色固體產物，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：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 至 B4 和 B6 的合成
中間物B1至B4和B6是以1-溴-2-碘苯 (1-bromo-2-iodobenzene)與芳硼酸(boronic acid，即反應物A)，中間物Bn的合成路徑係如合成機制B1所示。在合成機制B1中，「反應物A」係選自表2中的反應物A1至A5，「中間物Bn (Intermediate Bn)」係選自於包括前述中間物B1至B4的群組。合成機制B1
中間物B1至B4和B6是根據合成機制B1中的步驟所合成。
將1.0當量的1-溴-2-碘苯、1.2當量的芳硼酸(反應物A)、3當量的碳酸鉀、200毫升的甲苯、0.06當量的三間基苯基膦(tri(m-tolyl)phosphine，P(m-toyl)3 )和0.015當量的醋酸鈀於80°C下攪拌混合12小時，再冷卻至室溫，接著以飽和氯化鈉水溶液和醋酸乙酯萃取有機層、以硫酸鎂乾燥再以活性碳於矽膠管柱中過濾純化；產物於濃縮後經減壓過濾並以己烷洗滌而獲得中間物B，上述中間物B皆以上述方法進行分析，並將結果列於表2中。 表2：用以合成中間物B1至B4和B6的反應物A以及中間物B1至B4和B6的化學結構式、產率和以FD-MS分析的分子式與質量。
中間物 B5 的合成
除了上述合成機制B1，中間物B5另可以合成機制B2來合成。合成機制B2
步驟1：合成中間物B5-1
將0.05當量的雙三苯基膦氯化鈀(dichloro bis-(triphenylphosphine) palladium)和1當量的2-溴苯甲醛混合於一0.13至0.15M的四氫呋喃中，再加入3.0當量的三乙基胺和0.05當量的碘化銅；接著，於室溫下攪拌24小時，再以飽和氯化銨水溶液快速冷卻、以醋酸乙酯萃取三次並以滷水洗滌；再以硫酸鈉乾燥並以減壓脫氣過濾，獲得一初產物，該初產物經矽膠管柱層析後獲得中間物B5-1的產率為92.4%，FD-MS的分析結果為如下，分子式：C15 H10 O，理論分子量：206.64，實際分子量：206.64。
步驟2：合成中間物B5
將1.0當量的中間物B5-1、0.05當量的三氟甲烷磺酸酮(copper(II) trifluoromethanesulfonate，Cu(OTf)2 )混合於相當於中間物B5-1五倍體積的1,2-二氯乙烷中，再依序於室溫和通以氬氣的環境下加入1.2當量的1-(2-溴乙炔基苯) (1-(2-bromoethynyl)benzene)和1.0當量的三氟醋酸形成一混合物，並使該混合物於100°C下攪拌15分鐘再冷卻至室溫；接著，以飽和碳酸氫鈉水溶液萃取混合物三次、以硫酸鎂乾燥、蒸乾再以己烷作為洗提液於矽膠管柱層析得中間物B5，產率為80%，FD-MS的分析結果為如下，分子式：C16 H11 Br，理論分子量：283.16，實際分子量：283.16。
中間物 B1 至 B6 的修飾
除了中間物B1至B6之外，所屬領域具有通常知識者可採用除了1-溴-2-碘苯的其他二鹵代苯與有別於反應物A1至A5的芳基硼酸反應，以類似於合成機制B1的合成步驟成功合成其他中間物Bn；同樣的，所屬技術領域具有通常知識者亦可採用除了2-溴苯甲醛外的其他鹵代芳香醛以類似於合成機制B2的方式合成出除了中間物B1至B6之外的其他中間物Bn。例如下列中間物B7至B14：
中間物 Cn 的合成
前述中間物B1至B14(尤其指中間物B1至B5)可另用於合成中間物Cn，中間物Cn的合成路徑係如合成機制C1所示。在合成機制C1中，「中間物An」係選自於包括中間物A1至A15及其相似物的群組；「中間物Bn」係選自於包括中間物B1至B14及其相似物的群組；「中間物Cn」係選自於表3-1中包括中間物C1至C11的群組；中間物C1至C11分別以下述步驟所合成。合成機制C1
步驟1：醇中間物的合成
1.0當量的中間物Bn溶於120毫升、0.4M的THF中，降溫至-78°C後緩慢加入1.0當量、2.5M的正丁基鋰(n -Butyllithium，n -BuLi)並攪拌1小時，接著將0.7當量的中間物An加入反應溶液中並於室溫下再攪拌3小時，反應完成後，以飽和氯化銨水溶液冷卻反應溶液並萃取有機相，分離有機相後以石油醚再結晶產物獲得白色產物。
接著使白色產物以FD-MS分析，以中間物C1-1為例，FD-MS的分析後的分子式：C37 H23 BrO2 ，理論分子量：579.48，實際分子量：579.48。各醇中間物Cn-1不需進一步純化即可用於步驟2，以不同中間物An和中間物Bn合成的醇中間物Cn-1的化學結構式以及FD-MS的測量結果列於表3-1中。
步驟2：中間物Cn的合成
將1.0當量的醇中間物Cn-1、醋酸(相較於反應物w/v=1/3)和五滴硫酸混合並於110°C下攪拌6小時，再以旋轉蒸發器去除溶劑，並藉由管柱層析純化，再以甲苯使殘餘物在結晶獲得中間物Cn，中間物C1至C11以FD-MS分析確定，並將分析結果列於表3-1中。 表3-1：合成中間物C1至C11使用的中間物An和Bn；醇中間物的化學結構式；中間物C1至C11的化學結構式和產率以FD-MS側得的分子式和質量。
中間物 C1 至 C11 的修飾
除了前述中間物C1至C11，所屬領域具有通常知識者可藉由置換除了中間物A1至A4外的其他中間物An，或是置換除了中間物B1至B5的其他中間物Bn，使用類似於反應機制C1的合成路徑合成出其他中間物Cn，例如下列的中間物C12至C23：
中間物 Cn-B 的合成
前述中間物Cn可再藉由Miyaura硼基化反應 (Miyaura borylation reaction)進一步修飾為中間物Cn-B，「中間物Cn-B」是將中間物Cn的溴基取代為頻那醇硼基 [(pinacolato)boron group]，中間物Cn-B可藉由下述合成機制C1-B中的合成路徑合成。合成機制C1-B
1.2當量的聯硼酸頻那醇酯 [bis(pinacolato)diboron]、1.0當量的中間物Cn、0.015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)]和3.0當量的醋酸鉀於在0.3M的無水1,4-二噁烷 (1,4-dioxane)中形成的混合溶液，並在110°C的氮氣環境下攪拌8小時，待冷卻至室溫後，於低壓環境下去除溶劑，並將殘餘物以管柱層析純化獲得白黃色產物。該白黃色產物的化學結構式和產率以及FD-MS分析的分子式和質量結果列於表3-2中。 表3-2：合成中間物Cn-B使用的中間物Cn以及中間物Cn-B的化學結構式和產率以FD-MS分析而得的分子式和質量。
中間物 Cn-B 的修飾
除了上述中間物C1-B、C2-B、C4-B、C6-B、C8-B和C10-B之外，所屬領域具有通常知識者可任選自前述中間物Cn所構成的群組中除了中間物C1、C2、C4、C6、C8和C10的其他中間物Cn，並以類似於合成機制C1-B的方式對任一中間物Cn進行Miyaura硼基化反應以合成中間物Cn-B，如下所示。
新穎化合物的合成
前述中間物C1至C11和C1-B至C11-B可依合成機制I用以合成所述新穎化合物，於合成機制I中，「反應物B」係選自於表4中包括反應物B1至B34的群組；「中間物C」係包含前述中間物Cn、Cn-B及其相似物。合成機制I 表4：反應物B1至B34的化學結構式和CAS編號。
1.0當量的中間物Cn、2.1當量的反應物Bn、0.01當量的醋酸鈀、0.04當量的2-(二環己基磷基)聯苯 [dicyclohexylphosphine(2-biphenyl)，P(Cy)2 (2-biPh)]、甲苯/乙醇(0.5M、v/v=10/1)和3.0 M的碳酸鉀水溶液混合，於氮氣環境下以100°C的溫度下回流12小時，反應完全後，將水和甲苯加入反應物溶液中，接著，使用溶劑將有機相萃取出來並以硫酸鈉乾燥，於低壓環境下使溶劑揮發後利用矽膠管柱層析純化剩餘物，並以甲苯再結晶獲得新穎化合物
用以合成化合物I至XII的反應物Bn和中間物C列於表5中，各化合物I至XII分別以氫核磁共振光譜儀 (H1 -NMR)和FD-MS分析確定，化合物I至XVIII的氫核磁共振光譜圖如依序為圖2至圖13，且化合物I至XII的化學結構式、產率、分子式和質量列於表5中。 表5：合成化合物I至XII使用的反應物B和中間物C以及化合物I至XII的化學結構式和產率以FD-MS分析而得的分子式和質量。
化合物 I 至 XII 的修飾
除了前述化合物I至XII之外，所屬技術領域具有通常知識者可更替不同的中間物C(即中間物Cn或Cn-B)和反應物B，並以類似於合成機制I的合成路徑合成出其他新穎化合物。
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，並獲得實施例1至29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的材料和添加於HIL-2的摻雜物；HI-2是用於形成HIL-2的材料；HT-1和HT-2分別是用於形成HTL-1和HTL-2的材料；傳統ET材料和本發明的新穎化合物是用於形成ETL的材料；Liq是添加於ETL的摻雜物和形成EIL的材料；RH/GH/BH分別為形成REL/GEL/BEL的主要材料；RD/GD/BD分別可作為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5的新穎化合物所製成。上述各傳統材料的詳細化學結構式列於表6。 表6：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，用以製備紅光OLED的各有機層的材料和厚度分別列於表7中。 表7：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，各有機層依序沉積於ITO基板上，用以製備綠光OLED的各有機層的材料和厚度分別列於表8中。 表8：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，各有機層依序沉積於ITO基板上，用以製備藍光OLED的各有機層的材料和厚度分別列於表9中。 表9：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10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1至29和比較例1至3中OLED裝置的ETL材料、CIE顏色、驅動電壓、電流效率和外部量子效率(external quantum efficiency，EQE)列於表10中。 表10：實施例1至29和比較例1至3中OLED裝置的特性及效能表現。
根據表10的結果，相較於用於商業上電子傳輸材料(BCP)，本發明藉由添加化合物I至XII於電子傳輸層中，可降低紅光、綠光或藍光OLED裝置的驅動電壓並改善電流效率和外部電流效率，證實本發明的新穎化合物適用添加於各色OLED裝置中，並可達到降低驅動電壓、改善電流效率和改善外部電流效率的功效。
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13分別為化合物I至XII的氫核磁共振光譜圖。
無

Claims (15)

  1. 一種化合物，其係如下式(I)所示：其中，X1和X2分別獨立為C(Ra)，該二(Ra)彼此相同或不同，該二(Ra)相互連接形成一苯環；X3和X4分別獨立為C(Rb)，該二(Rb)彼此相同或不同，該二(Rb)相互連接形成一第二芳香環，該第二芳香環為一多環芳香環；Z1至Z12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、碳數為1至40的烷基、碳數為2至40的烯基、碳數為2至40的炔基、碳數為3至60的環烷基、碳數為3至60的雜環烷基、碳數為6至60的芳香基、碳數為3至60的雜芳基、碳數為1至40的烷氧基、碳數為6至60的芳氧基、碳數為1至40的矽烷基、碳數為6至60的芳矽基、碳數為1至40的硼烷基、碳數為6至60的芳硼基、碳數為1至40的膦基和碳數為1至40的氧膦基。
  2. 如請求項1所述之化合物，其中該多環芳香環是選自於由下列所構成的群組：萘環、蒽環、菲環、花環、9,9-二甲基芴環、苯並菲環、苯並花環、熒蒽環、三亞苯環和苯並熒蒽環。
  3. 如請求項1所述之化合物，其中該化合物係以任一下述式(I-I)至(I-XII)表示： 其中，n1為0至4的正整數，T選自於由下列所構成的群組：氫原子、氘原子、甲基、乙基、丙基、丁基、戊基、己基及苯基。
  4. 如請求項1至3中任一項所述之化合物，其中該Z1至Z8中的至少一者係選自於由下列所構成的群組：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6至60的芳香基、具有至少一官能基且碳數為3至60的雜芳基、具有至少一官能基且碳數為1至40的烷氧基、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；其中，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。
  5. 如請求項1至3中任一項所述之化合物，其中該Z1至Z8中的至少一者係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、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0至4的正整數；m為0至3的正整數；o是0至3的正整數；m和o的總和小於或等於5。
  6. 如請求項1至3中任一項所述之化合物，其中該Z1、Z2、Z3、Z6、Z7和Z8中的至少一者係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、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0至4的正整數；m為0至3的正整數；o是0至3的正整數；m和o的總和小於或等於5；Z4和Z5各自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、碳數為1至12的烷基、碳數為2至12的烯基和碳數為2至12的炔基。
  7. 如請求項1至3中任一項所述之化合物，其中該Z2、Z3、Z6和Z7中至少一者是是選自於由下列所構成的群組：
  8. 如請求項1至3中任一項所述之化合物，其中該Z1、Z2、Z3、Z6、Z7和Z8中至少一者是一經二苯基、二吡啶基、二嘧啶基、二吡嗪基、二噠嗪基、二苯並吡啶基、二苯並嘧啶基、二苯並吡嗪基或二苯並噠嗪基取代的三嗪基。
  9. 如請求項1至3中任一項所述之化合物，其中該Z9至Z12可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、碳數為1至12的烷基、碳數為2至12的烯基和碳數為2至12的炔基。
  10. 如請求項1所述之化合物，其中該化合物是選自於由下列所構成的群組：
  11. 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10中任一項所述的化合物。
  12. 如請求項11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。
  13. 如請求項12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。
  14. 如請求項12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。
  15. 如請求項11所述的有機電子裝置，其中該化合物係選自於由下列所構成的群組：
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