TWI658038B - 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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TWI658038B
TWI658038B TW106141189A TW106141189A TWI658038B TW I658038 B TWI658038 B TW I658038B TW 106141189 A TW106141189 A TW 106141189A TW 106141189 A TW106141189 A TW 106141189A TW I658038 B TWI658038 B TW I658038B
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carbons
ring
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TW106141189A
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TW201821415A (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，其中X1 和X2 各自獨立為C(Ra )，該二(Ra )彼此相同或不同，該二(Ra )相互連接形成一芳香環；X3 和X4 各自獨立為C(Rb )，該二(Rb )彼此相同或不同，該二(Rb )相互連接形成具有至少一呋喃基、至少一噻吩基或至少一二氧化噻吩基的一雜芳環。

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： 其中，X1和X2各自獨立為C(Ra)，該二(Ra)彼此相同或不同，該二(Ra)相互連接形成一芳香環；其中，X3和X4各自獨立為C(Rb)，該二(Rb)彼此相同或不同，該二(Rb)相互連接形成具有至少一呋喃基(furan group)、至少一噻吩基(thiophene group)或至少一二氧化噻吩基(thiophene S,S-dioxide group)的一雜芳環；其中，Z1至Z12係各自獨立選自於由下列所構成的群組：氫原子、氘原子、三氟甲基(trifuloromethyl group)、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、環上碳數為3至60的環烷基、環上碳數為3至60的雜環烷基、環上碳數為6至60的芳香基、環上碳數為3至60的雜芳基、碳數為1至40的烷氧基、環上碳數為6至60的芳氧基、碳數為1至40的矽烷基(alkylsilyl group)、環上碳數為6至60的芳矽基(arylsilyl group)、碳數為1至40的硼烷基(alkylboron group)、環上碳數為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X1和X2包含的雙鍵和該二(Ra)連接形成的鍵相互共軛且構成該芳香環；相同的，式(I)中X3和X4包含的雙鍵和該二(Rb)連接形成的鍵相互共軛且構成該雜芳環。根據本發明，自X1和X2延伸形成的該芳 香環和自X3和X4延伸形成的該雜芳環相互連接並合，且該芳香環的雙鍵和該雜芳環的雙鍵相互共軛。
較佳的，Z1至Z12係各自獨立選自於由下列所構成的群組：氫原子、氘原子、三氟甲基、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、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至30的雜芳基、碳數為1至12的烷氧基、環上碳數為6至30的芳氧基、碳數為1至12的矽烷基、環上碳數為6至30的芳矽基、碳數為1至12的硼烷基、環上碳數為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。
較佳的，式(I)中由X3和X4延伸形成的該雜芳環具有至少一呋喃基。例如，該雜芳環可以是苯並呋喃環(benzofuran ring)、二苯並呋喃環(dibenzofuran ring)或萘並呋喃環(napththofuran ring)，但不限於此。
當自X3和X4延伸的雜芳環包含有至少一呋喃基時，該化合物可表示如下式(I-I)至(I-VI)：
較佳的，式(I)中由X3和X4延伸形成的該雜芳環具有至少一噻吩基。例如，該雜芳環可以是苯並噻吩環(benzothiophene ring)、二苯並噻吩環(dibenzothiophene ring)或萘並噻吩環(napththothiophene ring)，但不限於此。
當自X3和X4延伸的雜芳環包含有至少一噻吩基時，該化合物可表示如下式(I-VII)至(I-XII)：
當自X3和X4延伸的雜芳環包含有至少一二氧化噻吩基時，該化合物可表示如下式(I-XIII)至(I-XVIII)：
根據本發明，上述A1和A2各自獨立為C(Rc)，該二(Rc)彼此相同或不同，該二(Rc)相互連接形成一芳香結構，該芳香結構係包含在由前述X3和X4所延伸成型之雜芳環中。
較佳的，該芳香結構為一經取代或未經取代且碳數為6至20的芳香環狀結構。例如：一經取代或未經取代的苯環結構(benzene structure)、一經取代或未經取代的萘環結構(naphthalene structure)、一經取代或未經取代的蒽環結構(anthracene structure)、一經取代或未經取代的菲環結構(phenanthrene structure)、一經取代或未經取代的芴環結構(fluorene structure)、一經取代或未經取代的芘環結構(pyrene structure)、一經取代或未經取代的苯並菲結構(benzophenanthrene structure)、一經取代或未經取代的苯并芘結構(benzopyrene structure)、一經取代或未經取代的熒蒽環結構(fluoranthene structure)或一經取代和未經取代的苯並熒蒽環結構(benzofluoranthene structure)，但不限於此；該碳數為6至20的芳香環狀結構上的取代基可以為以下基團，但不限於：一鹵基、一氰基、一硝基、一碳數為1至12的烷基、一碳數為2至12的烯基或一碳數為2至12的炔基。
較佳的，上述任一通式中由X1和X2所延伸形成的該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，由X1和X2所延伸形成的該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的碳環可選自於由下列所構成的群組：一經取代或未經取代的苯環、一經取代或未經取代的萘環、一經取代或未經取代的蒽環、一經取代或未經取代的菲環、一經取代或未經取代的芴環、一經取代或未經取代的芘環、一經取代或未經取代的苯並菲環、一經取代或未經取代的苯并芘環、一經取代或未經取代的熒蒽環和一經取代和未經取代的苯並熒蒽環，但不限於此。更佳的，該經取代或未經取代且碳數為6至60的碳環為經取代或未經取代的苯環結構。該碳數為6至20的碳環上的取代基可以為以下基團：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，但不限於此。
較佳的，該上述任一通式中的Z1至Z8中至少一者是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環上碳數為3至60的環烷基、具有至少一官能基且環上碳數為3至60的雜環烷基、具有至少一官能基且環上碳數為6至60的芳香基、具有至少一氮原子且環上碳數為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環上碳數為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環上碳數為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環上碳數為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；而上述任一通式中的Z1至Z8中的其他者可以為氫原子、氘原子或說明書提及的其他取代基。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。
具體而言，上述任一通式中的Z1至Z8中至少一者是特定的芳香取代基，且該特定的芳香取代基是選自於由下列所構成的群組： 其中，R1至R7係各自獨立選自於由下列所構成的群組：氫原子、氘原子、三氟甲基、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、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至20的雜芳基、碳數為1至40的烷氧基、環上碳數為6至30的芳氧基、碳數為1至40的矽烷基、環上碳數為6至30的芳矽基、碳數為1至40的硼烷基、環上碳數為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，但不限於此。
於其中一實施態樣中，上述任一通式中的Z1至Z8中至少一者為，其中，R1可以是吡啶基或苯氰基(cyanophenyl)，R2和R3可以是上述之任一取代基。
於另一實施態樣中，上述任一通式中的Z1至Z8中至少一者為，其中，R2可以是吡啶基或苯氰基，R1和R3可以是上述之任一取代基。
於再一實施態樣中，上述任一通式中的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的三嗪基(triazine group)。
較佳的，上述任一通式中的Z1、Z2、Z3、Z6、Z7和Z8中至少一者是前述特定的芳香取代基，而Z4、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。或者，上述任一通式中的Z2、Z3、Z6和Z7中至少一者是前述特定的芳香取代基，而Z1、Z4、Z5、Z8各自獨立選自於由下列所構成的群組：氫原子、氘原子、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。
較佳的，上述任一通式中的Z2、Z3、Z6和Z7中至少一者是選自於由下列所構成的群組：
更佳的，上述任一通式中的Z9至Z12可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。
根據本發明，上述任一通式中的的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。
舉例而言，上述任一通式中的Z1及Z4至Z8可各自獨立為氫原子或氘原子，Z2及/或Z3可以是上述特定的芳香取代基。或者，Z1、Z2、Z4、Z5、Z7和Z8可各自獨立為氫原子或氘原子，且Z3及Z6二者皆是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CCLXII)所製成，本發明以該新穎化合物作為電子傳輸層材料的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設置有電洞阻擋層和/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(N 1 -(1-萘基))-N 4 ,N 4' -二苯基苯-1,4-二胺[N 1 ,N 1’ -(biphenyl-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4’ -diphenylbenzene-1,4-diamine)]或N 4 ,N 4' -二(萘-1-基)-N 4 ,N 4’ -二苯聯苯基-4,4'-二胺[N 4 ,N 4' -di(naphthalen-1-yl)-N 4 ,N 4’ -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。
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28分別為化合物I至XXVII的氫核磁共振光譜圖。
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。
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℃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：C15H9Br3O，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和呋喃(furan，1.5當量)溶解於四氫呋喃(tetrahydrofuran，THF，1.0M)中，降溫至0℃，再加入87.8克(3.0當量)的叔丁醇鉀(potassium tert-butoxide，K-OtBu)後於0℃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淡黃色固體產物，產率為60.3%。
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：C19H11BrO2，理論值351.19，檢測值為351.19。
步驟3：合成中間物A1-3
將1.0當量的中間物A1-2懸浮液和0.025當量、5%的鈀碳催化劑(palladium on carbon，Pd/C)於2.0M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：C19H13BrO2，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
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：C19H11BrO，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。
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A12、 中間物A13、 中間物A14和 中間物A15。
中間物B1至B6的合成
中間物B1至B6是以1-溴-2-碘苯(1-bromo-2-iodobenzene)與雜芳基硼酸反應而得，雜芳基硼酸為「反應物An(Reactant An)」，中間物B的合成路徑係如合成機制Bn所示。在合成機制B中，反應物An係選自下表2中反應物A1至A6，「中間物Bn(Intermediate Bn)」係選自於包括前述中間物B1至B6的群組。
根據合成機制B，中間物B1至B6係根據以下步驟進行合成：將水和甲苯置於一圓底燒瓶中形成一混合液，並裝設一通有氬氣的冷凝器於圓底燒瓶上，藉由通以氬氣使混合液攪動混合。接著，將1.5當量的碳酸鉀、1當量的1-溴-2碘苯、1.2當量的反應物An、3當量的碳酸鉀、200毫升的甲苯、0.06當量的三苯基膦(triphenylphosphine，PPh3)和0.015當量的乙酸鈀於70℃的油浴下加熱攪拌反應5小時形成反應混合液，當反應完成後，使混合液冷卻至室溫後，藉由飽和食鹽水和EA萃取獲得有機層並以硫酸鎂除水，接著以矽膠過濾，再將濾物以己烷洗滌並過濾獲得中間物Bn。在合成機制B中所有中間物Bn的分析方法皆同前述，分析結果列於下表2。
中間物B1至B6的修飾
除了中間物B1至B6之外，所所屬技術領域具有通常知識者可以其他二鹵代苯(dihalobenzene)代替1-溴-2碘苯，亦可以其他雜芳基硼酸代替反應物A1至A6，再藉由類似於合成機制B的合成路徑合成出其他中間物Bn，舉例來 說，根據上述方法可合成出類似於中間物B1至B6的中間物B7和B8，如下所示：
中間物C的合成
前述中間物B1至B8(尤其是中間物B1至B6)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」可以是任一選自於中間物A1至A15或其相似之中間物，「中間物Bn」可以是任一選自於中間物B1至B8或其相似之中間物，「中間物Cn」可以是任一選自於表3-1中所示之中間物C1至C9或其相似的中間物。中間物C1至C9分別以下述步驟所合成。
步驟1：醇中間物的合成
1.0當量的中間物Bn溶於120毫升的無水THF(0.4M)，降溫至-78℃後緩慢加入正丁基鋰(n-butyllithium，n-BuLi)(2.5M，1.0eq)形成反應溶液並攪拌1小時。接著，將中間物An(0.7eq)加入反應溶液中於室溫下再攪拌3小時， 待反應完成後，以飽和氯化銨水溶液冷卻該反應溶液，再以有機溶劑萃取使有機相分離，於濃縮後使用石油醚再結晶以獲得白色固體產物。
該白色產物以FD-MS分析確定為醇中間物，以中間物C1-1為例，FD-MS的分析結果為如下，分子式：C37H23BrO2，理論分子量：579.48，實際分子量：579.48。
該醇中間物不需另外純化即可直接使用於步驟2。並對不同中間物An和中間物Bn合成的所有醇中間物以FD-MS進行分析確定，所使用的各中間物An、中間物Bn和醇中間物的化學結構式列於表3-1。
步驟2：中間物Cn的合成
混合1當量的醇中間物、醋酸(相較於反應物，w/v=1/3)和5滴硫酸並在110℃下攪拌6小時，接著於低壓環境下去除溶劑，於管柱層析純化後以甲苯再結晶最後獲得白色固體產物。
該固體產物經FD-MS進行分析確定，各中間物C1至C9的化學結構式、產率、分子式和質量列於表3-1。
中間物C1至C9的修飾
除了前述中間物C1至C9，所屬領域具有通常知識者可採用其他有別於中間物A1至A3的中間物An以及/或有別於中間物B1至B6的中間物Bn，經由類似於反應機制C1合成路徑合成出其他中間物Cn。本發明之中間物C1至C9的可適當修飾為下列的中間物C10至C33，但並非僅限於下方之例子：
前述中間物C6至C9和C22至C33可再進一步被氧化合成出其他中間物Cn，以中間物C6和C7為例，中間物C6和C7可分別藉由合成機制C2和C3被氧化成中間物C34和C35。
中間物C34的合成
將30%、1.52毫升的過氧化氫水溶液在0℃的溫度下逐滴加入75毫升的三氟乙酸中形成三氟過氧乙酸(trifluoroperacetic acid，TFA)溶液，並於滴加完成後移除冰浴，接著於攪拌的狀態下將中間物C6(5g、1.0eq)緩慢加入三氟過氧乙酸溶液中，反應完成後以水洗滌反應物溶液並於過濾後獲得固體，接著，將粗產物以矽膠管柱層析獲得3.3克、產率為62.5%的中間物C34，以FD-MS分析確定其分子式為：C37H21BrO2S，理論分子量：609.53，測量分子量：609.53。
中間物C35的合成
中間物C35是以類似於中間物C34的方式合成，其差異在於，中間物C6以中間物C7替代。固體產物以FD-MS分析確定為中間物C35，產率為85%，FD-MS分析結果：分子式為C37H21BrO2S，理論分子量為609.53，測量分子量為609.53。
中間物C34和C35的修飾
除了中間物C34和C35之外，所屬技術領域可選用具噻吩基的中間物Cn(例如中間物C8、C9、C22至C33)，並以類似於合成機制C2或C3的步驟來合成其他中間物Cn，例如下列中間物C36至C46：
中間物Cn-B的合成
前述中間物Cn可藉由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。
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℃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。該白黃色產物以FD-MS分析的結果列於表3-2中。
中間物Cn-B的修飾
除了上述中間物Cn-B之外，所屬技術領域具通常知識者可任選自前述中間物Cn所構成的群組，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
各中間物Cn以及中間物Cn-B可分別與不同的反應物合成出新穎化合物，新穎化合物可藉由下述合成機制I中的步驟進行合成。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」係選自於前述包括中間物Cn、中間物Cn-B及其相似物構成的群組。
1.0當量的中間物Cn、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)、3.0M的碳酸鉀水溶液和1.2當量的反應物Bn形成的混合液於氮氣環境下在100℃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XXVII的反應物Bn和中間物Cn列於表5中，各化合物I至XXVII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XXVII的氫核磁共振光譜圖如依序為圖2至圖28，且化合物I至XXVII的化學結構式、產率、分子式和質量列於表5中。
化合物I至XXVII的修飾
除了前述化合物I至XXVII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Bn，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1500Å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1x10-6torr至3x10-7torr，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19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的材料和作為HIL-2中的摻雜物；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；傳統的ET和本發明的新穎化合物是用於形成ETL的材料；Liq是用於形成EIL的材料和作為ETL中的摻雜物；RH/GH/BH分別為形成REL/GEL/BEL的主要材料；RD/GD/BD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。上述各化合物的詳細化學結構式列於表6。
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7中。
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8中。
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9中。
OLED裝置的效能
為了評估OLED裝置的效能，分別將紅光(R)、綠光(G)和藍光(B)的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 Internationalede 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19和比較例1至3中OLED裝置的ETL材料、顏色和CIE數據、驅動電壓、電流效率和外部量子效率(external quantum efficiency，EQE)列於下表10中。
根據表10的結果，相較於用於商業上OLED的材料(BCP)，本發明藉由添加化合物I至XXVII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量子效率，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和改善電流效率的功效。
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。

Claims (17)

  1. 一種化合物，其係如下式(I)所示：其中，X1和X2各自獨立為C(Ra)，該二(Ra)彼此相同或不同，該二(Ra)相互連接形成一芳香環；其中，X3和X4各自獨立為C(Rb)，該二(Rb)彼此相同或不同，該二(Rb)相互連接形成具有至少一呋喃基、至少一噻吩基或至少一二氧化噻吩基的一雜芳環；其中，Z1至Z12係各自獨立選自於由下列所構成的群組：氫原子、氘原子、三氟甲基、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、環上碳數為3至60的環烷基、環上碳數為3至60的雜環烷基、環上碳數為6至60的芳香基、環上碳數為3至60的雜芳基、碳數為1至40的烷氧基、環上碳數為6至60的芳氧基、碳數為1至40的矽烷基、環上碳數為6至60的芳矽基、碳數為1至40的硼烷基、環上碳數為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；其中當Z1至Z8中至少一者係環上碳數為3至60的雜芳基時，該環上碳數為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、三氟甲基、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、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至20的雜芳基、碳數為1至40的烷氧基、環上碳數為6至30的芳氧基、碳數為1至40的矽烷基、環上碳數為6至30的芳矽基、碳數為1至40的硼烷基、環上碳數為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。
  2. 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-XVIII)所示： 其中，A1和A2分別獨立為C(Rc)，該二(Rc)彼此相同或不同，該二(Rc)相互連接形成一芳香結構，該芳香結構係包含在由前述X3和X4所延伸成型之雜芳環。
  3. 如請求項2所述之化合物，其中該雜芳環中的芳香結構為一經取代或未經取代且碳數為6至20的芳香環狀結構。
  4. 如請求項3所述之化合物，其中該經取代或未經取代且碳數為6至20的芳香環狀結構係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芴環結構、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結構、一經取代或未經取代的苯并芘結構、一經取代或未經取代的熒蒽環結構和一經取代和未經取代的苯並熒蒽環結構。
  5. 如請求項1所述之化合物，其中由前述X1和X2所延伸成型之該芳香環為一經取代或未經取代且環上碳數為6至60的碳環。
  6. 如請求項5所述之化合物，其中該經取代或未經取代且碳數為6至60的碳環係選自於由下列所構成的群組：一經取代或未經取代的苯環、一經取代或未經取代的萘環、一經取代或未經取代的蒽環、一經取代或未經取代的菲環、一經取代或未經取代的芴環、一經取代或未經取代的芘環、一經取代或未經取代的苯並菲結構、一經取代或未經取代的苯并芘結構、一經取代或未經取代的熒蒽環和一經取代和未經取代的苯並熒蒽環。
  7. 如請求項6所述之化合物，其中該經取代或未經取代且碳數為6至60的碳環為經取代或未經取代的苯環。
  8. 如請求項1所述之化合物，其中該式(I)中Z1至Z8中至少一者是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環上碳數為3至60的環烷基、具有至少一官能基且環上碳數為3至60的雜環烷基、具有至少一官能基且環上碳數為6至60的芳香基、具有至少一氮原子且環上碳數為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環上碳數為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環上碳數為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環上碳數為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。
  9. 如請求項1所述之化合物，其中該式(I)中Z2、Z3、Z6和Z7中至少一者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、三氟甲基、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、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至20的雜芳基、碳數為1至40的烷氧基、環上碳數為6至30的芳氧基、碳數為1至40的矽烷基、環上碳數為6至30的芳矽基、碳數為1至40的硼烷基、環上碳數為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。該式(I)中Z1、Z4、Z5和Z8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的烯基和碳數為2至12的炔基所構成的群組。
  10. 如請求項9所述之化合物，其中該式(I)中Z2、Z3、Z6和Z7中至少一者是選自於由下列所構成的群組：
  11. 如請求項1所述之化合物，其中該式(I)中Z9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的烯基和碳數為2至12的炔基所構成的群組。
  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。
  17. 如請求項13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：
TW106141189A 2016-12-07 2017-11-27 化合物及其有機電子裝置 TWI658038B (zh)

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